data_global

_audit_creation_method            
;
manual editing of the CIF file 
created by SHELXL93
;

# 1. SUBMISSION DETAILS

_publ_contact_author_name
;
Beck, Johannes 
;
_publ_contact_author_address
;
Institute for Inorganic Chemistry
University of Bonn
Gerhard-Domagk-Str. 1
53121 Bonn
Germany
;

_publ_contact_author_phone    'intl. + 49 228 733114'
_publ_contact_author_fax      'intl. + 49 228 735660'
_publ_contact_author_email    j.beck@uni-bonn.de

_publ_requested_journal      
;
 Beilstein Journal of Organic Chemistry
;


# 2. TITLE AND AUTHOR LIST

_publ_section_title
;
 Macrocyclic Bis(ureas) as Ligands for Anion Complexation
;

loop_
_publ_author_name
_publ_author_address

;
'Fritschi, Claudia'
;
;
Institute for Inorganic Chemistry
University of Bonn
Gerhard-Domagk-Str. 1
53121 Bonn
Germany
;

;
'Dittmann, Gertrud'
;
;
Institute for Inorganic Chemistry
University of Bonn
Gerhard-Domagk-Str. 1
53121 Bonn
Germany
;


data_1
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 cyclo-bis(ethinyldiphenylurea) - bis(dimethylformamide)
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C40 H34 N6 O4' 
_chemical_formula_weight          662.73 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            triclinic 
_symmetry_space_group_name_H-M    P-1 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    8.2597(9) 
_cell_length_b                    9.7720(10) 
_cell_length_c                    11.0233(9) 
_cell_angle_alpha                 95.851(7) 
_cell_angle_beta                  99.783(8) 
_cell_angle_gamma                 100.761(9) 
_cell_volume                      853.13(15) 
_cell_formula_units_Z             1 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.290 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              348 
_exptl_absorpt_coefficient_mu     0.085 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             6682 
_diffrn_reflns_av_R_equivalents   0.0254 
_diffrn_reflns_av_sigmaI/netI     0.0346 
_diffrn_reflns_limit_h_min        -10 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -13 
_diffrn_reflns_limit_l_max        13 
_diffrn_reflns_theta_min          1.89 
_diffrn_reflns_theta_max          25.97 
_reflns_number_total              3341 
_reflns_number_gt                 2174 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0541P)²+0.0919P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.013(3) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3341 
_refine_ls_number_parameters      295 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0727 
_refine_ls_R_factor_gt            0.0364 
_refine_ls_wR_factor_ref          0.1048 
_refine_ls_wR_factor_gt           0.0903 
_refine_ls_goodness_of_fit_ref    0.991 
_refine_ls_restrained_S_all       0.991 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.20803(14) 0.66159(12) 0.33448(13) 0.0597(4) Uani 1 1 d . . . 
N1 N -0.00558(16) 0.76526(14) 0.25564(13) 0.0457(3) Uani 1 1 d . . . 
N2 N 0.26924(16) 0.87563(14) 0.26767(12) 0.0439(3) Uani 1 1 d . . . 
C1 C 0.16130(19) 0.75991(16) 0.29069(14) 0.0422(4) Uani 1 1 d . . . 
C2 C -0.14106(19) 0.66719(15) 0.28022(14) 0.0400(4) Uani 1 1 d . . . 
C3 C -0.2982(2) 0.64482(16) 0.20012(14) 0.0426(4) Uani 1 1 d . . . 
C4 C -0.4352(2) 0.55178(19) 0.22592(18) 0.0558(5) Uani 1 1 d . . . 
C5 C -0.4172(2) 0.4822(2) 0.32771(19) 0.0624(5) Uani 1 1 d . . . 
C6 C -0.2637(2) 0.5058(2) 0.40667(19) 0.0595(5) Uani 1 1 d . . . 
C7 C -0.1265(2) 0.59775(18) 0.38388(17) 0.0503(4) Uani 1 1 d . . . 
C8 C 0.44279(18) 0.91642(15) 0.31827(13) 0.0388(4) Uani 1 1 d . . . 
C9 C 0.53309(19) 1.03397(17) 0.27731(14) 0.0425(4) Uani 1 1 d . . . 
C10 C 0.7023(2) 1.0886(2) 0.33421(16) 0.0529(4) Uani 1 1 d . . . 
C11 C 0.7818(2) 1.0252(2) 0.42490(17) 0.0571(5) Uani 1 1 d . . . 
C12 C 0.6940(2) 0.9065(2) 0.46061(17) 0.0533(4) Uani 1 1 d . . . 
C13 C 0.5266(2) 0.85190(18) 0.40894(15) 0.0470(4) Uani 1 1 d . . . 
C14 C -0.3243(2) 0.71803(17) 0.09512(15) 0.0468(4) Uani 1 1 d . . . 
C15 C -0.3592(2) 0.77696(18) 0.00700(16) 0.0496(4) Uani 1 1 d . . . 
C16 C 0.45969(19) 1.09909(17) 0.17802(15) 0.0460(4) Uani 1 1 d . . . 
C17 C 0.4089(2) 1.15625(17) 0.09204(15) 0.0491(4) Uani 1 1 d . . . 
N3 N -0.03992(18) 1.24213(14) 0.12884(14) 0.0532(4) Uani 1 1 d . . . 
O2 O 0.02227(16) 1.03416(13) 0.16859(14) 0.0700(4) Uani 1 1 d . . . 
C18 C -0.0629(2) 1.10471(18) 0.11046(18) 0.0542(4) Uani 1 1 d . . . 
C19 C -0.1515(5) 1.3151(3) 0.0547(3) 0.0904(8) Uani 1 1 d . . . 
C20 C 0.0946(4) 1.3220(3) 0.2258(5) 0.1050(11) Uani 1 1 d . . . 
HN1 H -0.027(2) 0.8395(19) 0.2147(17) 0.057(5) Uiso 1 1 d . . . 
HN2 H 0.218(2) 0.9382(17) 0.2308(15) 0.045(4) Uiso 1 1 d . . . 
H4 H -0.541(3) 0.5425(19) 0.1697(17) 0.063(5) Uiso 1 1 d . . . 
H5 H -0.513(3) 0.418(2) 0.3411(17) 0.067(5) Uiso 1 1 d . . . 
H6 H -0.249(2) 0.4586(19) 0.4791(17) 0.061(5) Uiso 1 1 d . . . 
H7 H -0.025(2) 0.6137(18) 0.4386(17) 0.057(5) Uiso 1 1 d . . . 
H10 H 0.757(2) 1.173(2) 0.3054(17) 0.063(5) Uiso 1 1 d . . . 
H11 H 0.896(3) 1.0662(19) 0.4618(17) 0.066(5) Uiso 1 1 d . . . 
H12 H 0.747(2) 0.8600(18) 0.5255(17) 0.057(5) Uiso 1 1 d . . . 
H13 H 0.465(2) 0.7695(19) 0.4360(16) 0.056(5) Uiso 1 1 d . . . 
H18 H -0.165(3) 1.058(2) 0.043(2) 0.089(7) Uiso 1 1 d . . . 
H20 H -0.190(3) 1.378(3) 0.110(3) 0.107(9) Uiso 1 1 d . . . 
H22 H -0.240(5) 1.245(4) -0.004(3) 0.156(14) Uiso 1 1 d . . . 
H21 H -0.070(4) 1.377(3) 0.017(3) 0.141(12) Uiso 1 1 d . . . 
H24 H 0.073(6) 1.386(5) 0.268(4) 0.188(19) Uiso 1 1 d . . . 
H25 H 0.169(4) 1.259(4) 0.260(3) 0.146(12) Uiso 1 1 d . . . 
H26 H 0.146(7) 1.381(6) 0.182(5) 0.22(3) Uiso 1 1 d . . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C1 1.2144(17) . ? 
N1 C1 1.379(2) . ? 
N1 C2 1.4141(19) . ? 
N1 HN1 0.922(18) . ? 
N2 C1 1.3773(19) . ? 
N2 C8 1.4122(19) . ? 
N2 HN2 0.897(17) . ? 
C2 C7 1.387(2) . ? 
C2 C3 1.406(2) . ? 
C3 C4 1.402(2) . ? 
C3 C14 1.428(2) . ? 
C4 C5 1.371(3) . ? 
C4 H4 0.96(2) . ? 
C5 C6 1.376(3) . ? 
C5 H5 0.96(2) . ? 
C6 C7 1.385(2) . ? 
C6 H6 0.963(18) . ? 
C7 H7 0.924(19) . ? 
C8 C13 1.390(2) . ? 
C8 C9 1.407(2) . ? 
C9 C10 1.410(2) . ? 
C9 C16 1.425(2) . ? 
C10 C11 1.368(2) . ? 
C10 H10 0.970(19) . ? 
C11 C12 1.379(3) . ? 
C11 H11 0.95(2) . ? 
C12 C13 1.384(2) . ? 
C12 H12 0.972(18) . ? 
C13 H13 0.971(18) . ? 
C14 C15 1.200(2) . ? 
C15 C17 1.371(2) 2_575 ? 
C16 C17 1.203(2) . ? 
C17 C15 1.371(2) 2_575 ? 
N3 C18 1.310(2) . ? 
N3 C20 1.445(3) . ? 
N3 C19 1.461(3) . ? 
O2 O2 0.000(4) 1 ? 
O2 C18 1.224(2) . ? 
C18 O2 1.224(2) 1 ? 
C18 H18 1.03(2) . ? 
C19 H20 0.95(3) . ? 
C19 H22 0.99(4) . ? 
C19 H21 0.99(3) . ? 
C20 H24 0.81(5) . ? 
C20 H25 1.01(3) . ? 
C20 H26 0.88(5) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C1 N1 C2 124.43(13) . . ? 
C1 N1 HN1 116.3(11) . . ? 
C2 N1 HN1 119.3(11) . . ? 
C1 N2 C8 125.94(13) . . ? 
C1 N2 HN2 114.5(11) . . ? 
C8 N2 HN2 118.1(10) . . ? 
O1 C1 N2 123.50(14) . . ? 
O1 C1 N1 123.40(14) . . ? 
N2 C1 N1 113.08(13) . . ? 
C7 C2 C3 118.90(14) . . ? 
C7 C2 N1 122.27(14) . . ? 
C3 C2 N1 118.75(13) . . ? 
C4 C3 C2 119.38(14) . . ? 
C4 C3 C14 118.69(14) . . ? 
C2 C3 C14 121.89(14) . . ? 
C5 C4 C3 120.73(16) . . ? 
C5 C4 H4 123.2(11) . . ? 
C3 C4 H4 116.0(11) . . ? 
C4 C5 C6 119.66(17) . . ? 
C4 C5 H5 118.4(11) . . ? 
C6 C5 H5 122.0(11) . . ? 
C5 C6 C7 120.83(16) . . ? 
C5 C6 H6 120.8(11) . . ? 
C7 C6 H6 118.4(11) . . ? 
C6 C7 C2 120.48(16) . . ? 
C6 C7 H7 119.7(11) . . ? 
C2 C7 H7 119.8(11) . . ? 
C13 C8 C9 118.71(14) . . ? 
C13 C8 N2 124.15(14) . . ? 
C9 C8 N2 117.08(12) . . ? 
C8 C9 C10 119.52(14) . . ? 
C8 C9 C16 122.05(13) . . ? 
C10 C9 C16 118.43(14) . . ? 
C11 C10 C9 120.83(17) . . ? 
C11 C10 H10 123.1(11) . . ? 
C9 C10 H10 116.1(11) . . ? 
C10 C11 C12 119.08(17) . . ? 
C10 C11 H11 118.1(11) . . ? 
C12 C11 H11 122.8(11) . . ? 
C11 C12 C13 121.69(16) . . ? 
C11 C12 H12 120.8(11) . . ? 
C13 C12 H12 117.4(11) . . ? 
C12 C13 C8 120.07(16) . . ? 
C12 C13 H13 121.1(10) . . ? 
C8 C13 H13 118.8(10) . . ? 
C15 C14 C3 174.93(17) . . ? 
C14 C15 C17 176.45(18) . 2_575 ? 
C17 C16 C9 175.31(16) . . ? 
C16 C17 C15 177.10(17) . 2_575 ? 
C18 N3 C20 119.5(2) . . ? 
C18 N3 C19 120.7(2) . . ? 
C20 N3 C19 119.7(2) . . ? 
O2 O2 C18 0(10) 1 . ? 
O2 C18 O2 0.00(13) 1 . ? 
O2 C18 N3 125.57(19) 1 . ? 
O2 C18 N3 125.57(19) . . ? 
O2 C18 H18 120.9(12) 1 . ? 
O2 C18 H18 120.9(12) . . ? 
N3 C18 H18 113.5(12) . . ? 
N3 C19 H20 108.4(16) . . ? 
N3 C19 H22 109.5(19) . . ? 
H20 C19 H22 116(3) . . ? 
N3 C19 H21 100.8(19) . . ? 
H20 C19 H21 105(2) . . ? 
H22 C19 H21 116(3) . . ? 
N3 C20 H24 116(3) . . ? 
N3 C20 H25 110.1(19) . . ? 
H24 C20 H25 124(4) . . ? 
N3 C20 H26 100(4) . . ? 
H24 C20 H26 90(4) . . ? 
H25 C20 H26 112(4) . . ? 
 
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
N1 HN1 O2  0.922(18) 2.005(18) 2.8708(18) 155.6(15) 1 
N2 HN2 O2  0.897(17) 2.072(17) 2.9192(18) 157.1(14) 1 
 
_diffrn_measured_fraction_theta_max    1.000 
_diffrn_reflns_theta_full              25.97 
_diffrn_measured_fraction_theta_full   1.000 
_refine_diff_density_max    0.184 
_refine_diff_density_min   -0.161 
_refine_diff_density_rms    0.032 

data_2 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
  cyclo-bis(ethinyldiphenylurea) - bis(dimethylsulfoxide) 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C38 H32 N4 O4 S2' 
_chemical_formula_weight          672.80 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'S'  'S'   0.1246   0.1234 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P21/c 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    8.2244(13) 
_cell_length_b                    17.995(2) 
_cell_length_c                    12.1198(17) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  113.483(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      1645.1(4) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     123(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.358 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              704 
_exptl_absorpt_coefficient_mu     0.210 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       123(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             6646 
_diffrn_reflns_av_R_equivalents   0.1051 
_diffrn_reflns_av_sigmaI/netI     0.2040 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -19 
_diffrn_reflns_limit_k_max        22 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        10 
_diffrn_reflns_theta_min          2.83 
_diffrn_reflns_theta_max          25.96 
_reflns_number_total              3136 
_reflns_number_gt                 1261 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0177P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3136 
_refine_ls_number_parameters      227 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1531 
_refine_ls_R_factor_gt            0.0522 
_refine_ls_wR_factor_ref          0.1038 
_refine_ls_wR_factor_gt           0.0803 
_refine_ls_goodness_of_fit_ref    0.738 
_refine_ls_restrained_S_all       0.738 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
C1 C 0.1062(5) -0.1709(2) 0.2950(4) 0.0398(10) Uani 1 1 d . . . 
C2 C 0.3279(4) -0.2116(2) 0.4933(4) 0.0370(9) Uani 1 1 d . . . 
C3 C 0.3861(5) -0.2731(2) 0.4495(4) 0.0447(11) Uani 1 1 d . . . 
H3 H 0.3344 -0.2842 0.3660 0.054 Uiso 1 1 calc R . . 
C4 C 0.5189(5) -0.3179(2) 0.5270(4) 0.0488(11) Uani 1 1 d . . . 
H4 H 0.5563 -0.3599 0.4958 0.059 Uiso 1 1 calc R . . 
C5 C 0.5983(5) -0.3032(2) 0.6486(4) 0.0486(11) Uani 1 1 d . . . 
H5 H 0.6917 -0.3337 0.7005 0.058 Uiso 1 1 calc R . . 
C6 C 0.5389(4) -0.2429(2) 0.6936(4) 0.0415(10) Uani 1 1 d . . . 
H6 H 0.5912 -0.2327 0.7774 0.050 Uiso 1 1 calc R . . 
C7 C 0.4033(4) -0.1969(2) 0.6175(4) 0.0351(9) Uani 1 1 d . . . 
C8 C 0.3442(5) -0.1372(2) 0.6702(4) 0.0388(10) Uani 1 1 d . . . 
C9 C 0.3014(5) -0.0917(2) 0.7265(4) 0.0395(10) Uani 1 1 d . . . 
C10 C -0.0403(4) -0.0995(2) 0.1077(4) 0.0350(9) Uani 1 1 d . . . 
C11 C -0.1639(4) -0.04200(19) 0.0602(4) 0.0350(9) Uani 1 1 d . . . 
C12 C -0.2428(4) -0.0305(2) -0.0656(4) 0.0378(10) Uani 1 1 d . . . 
H12 H -0.3249 0.0089 -0.0981 0.045 Uiso 1 1 calc R . . 
C13 C -0.2001(5) -0.0769(2) -0.1411(4) 0.0452(10) Uani 1 1 d . . . 
H13 H -0.2543 -0.0698 -0.2257 0.054 Uiso 1 1 calc R . . 
C14 C -0.0778(5) -0.1339(2) -0.0931(4) 0.0435(11) Uani 1 1 d . . . 
H14 H -0.0480 -0.1653 -0.1452 0.052 Uiso 1 1 calc R . . 
C15 C 0.0010(5) -0.1452(2) 0.0302(4) 0.0412(10) Uani 1 1 d . . . 
H15 H 0.0838 -0.1845 0.0619 0.049 Uiso 1 1 calc R . . 
C16 C -0.2129(4) 0.0046(2) 0.1373(4) 0.0375(10) Uani 1 1 d . . . 
C17 C -0.2531(4) 0.0440(2) 0.2034(4) 0.0377(9) Uani 1 1 d . . . 
N1 N 0.0442(4) -0.10538(17) 0.2342(3) 0.0389(8) Uani 1 1 d . . . 
H1 H 0.0596 -0.0645 0.2770 0.047 Uiso 1 1 d R . . 
N2 N 0.2009(3) -0.16051(16) 0.4171(3) 0.0371(8) Uani 1 1 d . . . 
H2 H 0.1842 -0.1190 0.4496 0.045 Uiso 1 1 d R . . 
O1 O 0.0804(3) -0.23161(15) 0.2451(3) 0.0472(8) Uani 1 1 d . . . 
O2 O 0.1998(3) 0.00074(15) 0.4284(3) 0.0490(8) Uani 1 1 d . . . 
S1A S 0.20383(15) 0.05798(6) 0.51968(12) 0.0387(4) Uani 0.869(3) 1 d P . . 
S1B S 0.3088(11) 0.0720(5) 0.4655(9) 0.053(3) Uani 0.131(3) 1 d P . . 
C18 C 0.1686(5) 0.1461(2) 0.4486(4) 0.0560(14) Uani 1 1 d . . . 
H18A H 0.0447 0.1490 0.3887 0.067 Uiso 1 1 d R . . 
H18B H 0.1643 0.1896 0.5019 0.067 Uiso 1 1 d R . . 
H18C H 0.2497 0.1456 0.3978 0.067 Uiso 1 1 d R . . 
C19 C 0.4330(4) 0.0695(2) 0.6139(4) 0.0491(11) Uani 1 1 d . . . 
H19A H 0.4672 0.0187 0.6479 0.059 Uiso 1 1 d R . . 
H19B H 0.4894 0.0727 0.5617 0.059 Uiso 1 1 d R . . 
H19C H 0.4470 0.1193 0.6556 0.059 Uiso 1 1 d R . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
C1 O1 1.225(5) . ? 
C1 N1 1.376(5) . ? 
C1 N2 1.383(5) . ? 
C2 C3 1.392(5) . ? 
C2 C7 1.406(6) . ? 
C2 N2 1.421(4) . ? 
C3 C4 1.382(5) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.378(6) . ? 
C4 H4 0.9500 . ? 
C5 C6 1.387(6) . ? 
C5 H5 0.9500 . ? 
C6 C7 1.400(5) . ? 
C6 H6 0.9500 . ? 
C7 C8 1.430(6) . ? 
C8 C9 1.205(5) . ? 
C9 C17 1.373(6) 3_556 ? 
C10 C15 1.388(5) . ? 
C10 C11 1.404(5) . ? 
C10 N1 1.413(5) . ? 
C11 C12 1.414(6) . ? 
C11 C16 1.429(6) . ? 
C12 C13 1.382(6) . ? 
C12 H12 0.9500 . ? 
C13 C14 1.392(5) . ? 
C13 H13 0.9500 . ? 
C14 C15 1.386(6) . ? 
C14 H14 0.9500 . ? 
C15 H15 0.9500 . ? 
C16 C17 1.210(6) . ? 
C17 C9 1.373(6) 3_556 ? 
N1 H1 0.8799 . ? 
N2 H2 0.8800 . ? 
O2 S1A 1.502(3) . ? 
O2 S1B 1.525(9) . ? 
S1A S1B 1.301(9) . ? 
S1A C18 1.773(4) . ? 
S1A C19 1.785(3) . ? 
S1B C19 1.678(10) . ? 
S1B C18 1.721(9) . ? 
S1B H18C 1.5332 . ? 
S1B H19B 1.4782 . ? 
C18 H18A 0.9892 . ? 
C18 H18B 1.0257 . ? 
C18 H18C 1.0722 . ? 
C19 H19A 0.9965 . ? 
C19 H19B 0.9229 . ? 
C19 H19C 1.0124 . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
O1 C1 N1 123.0(4) . . ? 
O1 C1 N2 124.2(4) . . ? 
N1 C1 N2 112.8(3) . . ? 
C3 C2 C7 119.0(3) . . ? 
C3 C2 N2 122.8(4) . . ? 
C7 C2 N2 118.1(3) . . ? 
C4 C3 C2 120.2(4) . . ? 
C4 C3 H3 119.9 . . ? 
C2 C3 H3 119.9 . . ? 
C5 C4 C3 121.6(4) . . ? 
C5 C4 H4 119.2 . . ? 
C3 C4 H4 119.2 . . ? 
C4 C5 C6 118.6(4) . . ? 
C4 C5 H5 120.7 . . ? 
C6 C5 H5 120.7 . . ? 
C5 C6 C7 121.1(4) . . ? 
C5 C6 H6 119.5 . . ? 
C7 C6 H6 119.5 . . ? 
C6 C7 C2 119.3(4) . . ? 
C6 C7 C8 118.3(4) . . ? 
C2 C7 C8 122.4(3) . . ? 
C9 C8 C7 172.5(5) . . ? 
C8 C9 C17 175.8(5) . 3_556 ? 
C15 C10 C11 119.5(4) . . ? 
C15 C10 N1 122.9(3) . . ? 
C11 C10 N1 117.5(4) . . ? 
C10 C11 C12 119.7(4) . . ? 
C10 C11 C16 120.8(4) . . ? 
C12 C11 C16 119.5(3) . . ? 
C13 C12 C11 119.8(4) . . ? 
C13 C12 H12 120.1 . . ? 
C11 C12 H12 120.1 . . ? 
C12 C13 C14 120.0(4) . . ? 
C12 C13 H13 120.0 . . ? 
C14 C13 H13 120.0 . . ? 
C15 C14 C13 120.6(4) . . ? 
C15 C14 H14 119.7 . . ? 
C13 C14 H14 119.7 . . ? 
C14 C15 C10 120.4(4) . . ? 
C14 C15 H15 119.8 . . ? 
C10 C15 H15 119.8 . . ? 
C17 C16 C11 179.5(5) . . ? 
C16 C17 C9 176.7(5) . 3_556 ? 
C1 N1 C10 124.2(3) . . ? 
C1 N1 H1 117.8 . . ? 
C10 N1 H1 118.0 . . ? 
C1 N2 C2 124.2(3) . . ? 
C1 N2 H2 118.2 . . ? 
C2 N2 H2 117.6 . . ? 
S1A O2 S1B 50.9(4) . . ? 
S1B S1A O2 65.5(4) . . ? 
S1B S1A C18 66.1(4) . . ? 
O2 S1A C18 107.7(2) . . ? 
S1B S1A C19 63.6(4) . . ? 
O2 S1A C19 105.00(18) . . ? 
C18 S1A C19 97.7(2) . . ? 
S1A S1B O2 63.6(4) . . ? 
S1A S1B C19 72.4(5) . . ? 
O2 S1B C19 109.2(6) . . ? 
S1A S1B C18 70.3(4) . . ? 
O2 S1B C18 109.2(5) . . ? 
C19 S1B C18 103.9(6) . . ? 
S1A S1B H18C 107.7 . . ? 
O2 S1B H18C 123.0 . . ? 
C19 S1B H18C 121.6 . . ? 
C18 S1B H18C 37.9 . . ? 
S1A S1B H19B 105.3 . . ? 
O2 S1B H19B 121.8 . . ? 
C19 S1B H19B 33.2 . . ? 
C18 S1B H19B 120.2 . . ? 
H18C S1B H19B 114.8 . . ? 
S1B C18 S1A 43.7(3) . . ? 
S1B C18 H18A 125.1 . . ? 
S1A C18 H18A 109.0 . . ? 
S1B C18 H18B 135.0 . . ? 
S1A C18 H18B 114.6 . . ? 
H18A C18 H18B 97.9 . . ? 
S1B C18 H18C 61.5 . . ? 
S1A C18 H18C 104.7 . . ? 
H18A C18 H18C 105.9 . . ? 
H18B C18 H18C 123.6 . . ? 
S1B C19 S1A 44.0(3) . . ? 
S1B C19 H19A 114.7 . . ? 
S1A C19 H19A 102.1 . . ? 
S1B C19 H19B 61.4 . . ? 
S1A C19 H19B 105.0 . . ? 
H19A C19 H19B 101.8 . . ? 
S1B C19 H19C 114.3 . . ? 
S1A C19 H19C 107.7 . . ? 
H19A C19 H19C 130.4 . . ? 
H19B C19 H19C 107.5 . . ? 
 
_diffrn_measured_fraction_theta_max    0.973 
_diffrn_reflns_theta_full              25.96 
_diffrn_measured_fraction_theta_full   0.973 
_refine_diff_density_max    0.185 
_refine_diff_density_min   -0.244 
_refine_diff_density_rms    0.046 


data_3
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
Tetraethylammonium-cyclo-bis(butadiynyldiphenylurea)-bromide complex 
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C42 H36 Br1 N5 O2'
_chemical_formula_sum
 'C42 H40 Br N5 O2'
_chemical_formula_weight          726.70
 
loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Br'  'Br'  -0.2901   2.4595
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M    P21/c
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    12.7152(6)
_cell_length_b                    17.5556(8)
_cell_length_c                    20.5472(8)
_cell_angle_alpha                 90.00
_cell_angle_beta                  125.548(3)
_cell_angle_gamma                 90.00
_cell_volume                      3731.8(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     7920
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       25.35
 
_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.122
_exptl_crystal_size_mid           0.112
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.293
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1512
_exptl_absorpt_coefficient_mu     1.144
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.8719
_exptl_absorpt_correction_T_max   0.9225
_exptl_absorpt_process_details
;
Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;
 
_exptl_special_details
;
Department of Chemistry
University of Anywhere
Sometown
Somewhere, UK
;
 
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   KappaCCD
_diffrn_measurement_method        'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean  9
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             32096
_diffrn_reflns_av_R_equivalents   0.1425
_diffrn_reflns_av_sigmaI/netI     0.1014
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -21
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        24
_diffrn_reflns_theta_min          3.04
_diffrn_reflns_theta_max          25.40
_reflns_number_total              6837
_reflns_number_gt                 3078
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement        'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction         'HKL Denzo and Scalepack (Otwinowski & Minor'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material   'WinGX publication routines (Farrugia, 1999)'
 
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
 
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
 'calc w=1/[σ²(Fo²)+(0.0573P)²+1.5843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          6837
_refine_ls_number_parameters      535
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1654
_refine_ls_R_factor_gt            0.0617
_refine_ls_wR_factor_ref          0.1628
_refine_ls_wR_factor_gt           0.1230
_refine_ls_goodness_of_fit_ref    1.005
_refine_ls_restrained_S_all       1.005
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_symmetry_multiplicity
 _atom_site_calc_flag
 _atom_site_refinement_flags
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Br1 Br 0.03151(5) -0.00112(4) 0.28080(3) 0.0708(2) Uani 1 1 d . . .
O1 O 0.0863(4) 0.1731(2) 0.5090(2) 0.0762(12) Uani 1 1 d . . .
O2 O -0.0193(4) -0.1221(2) 0.0321(2) 0.0791(12) Uani 1 1 d . . .
N1 N -0.0302(5) 0.0892(3) 0.4054(3) 0.0600(13) Uani 1 1 d . . .
N2 N 0.1579(4) 0.1408(3) 0.4334(3) 0.0572(12) Uani 1 1 d . . .
N3 N 0.1002(5) -0.1025(3) 0.1664(3) 0.0633(15) Uani 1 1 d . . .
N4 N -0.0924(5) -0.0382(3) 0.0825(3) 0.0642(14) Uani 1 1 d . . .
C1 C 0.0740(5) 0.1370(3) 0.4543(3) 0.0564(14) Uani 1 1 d . . .
C2 C -0.1271(5) 0.0700(3) 0.4155(3) 0.0559(14) Uani 1 1 d . . .
C3 C -0.1054(6) 0.0715(3) 0.4900(4) 0.0646(16) Uani 1 1 d . . .
C4 C -0.2042(6) 0.0521(4) 0.4970(4) 0.0747(18) Uani 1 1 d . . .
C5 C -0.3218(7) 0.0308(4) 0.4311(4) 0.085(2) Uani 1 1 d . . .
C6 C -0.3439(7) 0.0268(4) 0.3578(4) 0.082(2) Uani 1 1 d . . .
C7 C -0.2472(5) 0.0485(3) 0.3488(3) 0.0618(15) Uani 1 1 d . . .
C8 C -0.2718(5) 0.0464(4) 0.2718(4) 0.0673(16) Uani 1 1 d . . .
C9 C -0.2844(5) 0.0439(4) 0.2097(4) 0.0663(16) Uani 1 1 d . . .
C10 C -0.2937(5) 0.0369(3) 0.1390(4) 0.0675(16) Uani 1 1 d . . .
C11 C -0.2975(5) 0.0300(3) 0.0801(3) 0.0677(16) Uani 1 1 d . . .
C12 C -0.3010(5) 0.0239(3) 0.0093(3) 0.0656(16) Uani 1 1 d . . .
C13 C -0.4074(7) 0.0540(4) -0.0621(4) 0.0778(19) Uani 1 1 d . . .
C14 C -0.4151(7) 0.0504(4) -0.1315(4) 0.081(2) Uani 1 1 d . . .
C15 C -0.3181(7) 0.0160(4) -0.1305(4) 0.0792(19) Uani 1 1 d . . .
C16 C -0.2074(6) -0.0146(3) -0.0610(3) 0.0731(18) Uani 1 1 d . . .
C17 C -0.2006(5) -0.0103(3) 0.0104(3) 0.0614(15) Uani 1 1 d . . .
C18 C -0.0046(5) -0.0898(3) 0.0893(3) 0.0600(15) Uani 1 1 d . . .
C19 C 0.2031(6) -0.1504(3) 0.1908(3) 0.0616(15) Uani 1 1 d . . .
C20 C 0.1940(7) -0.2122(3) 0.1436(4) 0.0717(17) Uani 1 1 d . . .
C21 C 0.3004(8) -0.2572(4) 0.1701(5) 0.088(2) Uani 1 1 d . . .
C22 C 0.4130(10) -0.2459(4) 0.2417(5) 0.098(3) Uani 1 1 d . . .
C23 C 0.4266(7) -0.1863(4) 0.2902(4) 0.0806(19) Uani 1 1 d . . .
C24 C 0.3225(5) -0.1380(3) 0.2649(3) 0.0603(14) Uani 1 1 d . . .
C25 C 0.3381(5) -0.0761(4) 0.3142(3) 0.0629(15) Uani 1 1 d . . .
C26 C 0.3494(5) -0.0227(4) 0.3546(3) 0.0620(16) Uani 1 1 d . . .
C27 C 0.3609(5) 0.0406(4) 0.3974(3) 0.0643(15) Uani 1 1 d . . .
C28 C 0.3685(5) 0.0984(4) 0.4323(3) 0.0633(15) Uani 1 1 d . . .
C29 C 0.3711(6) 0.1679(3) 0.4681(3) 0.0601(15) Uani 1 1 d . . .
C30 C 0.4784(6) 0.2170(4) 0.5009(4) 0.0765(19) Uani 1 1 d . . .
C31 C 0.4790(8) 0.2857(4) 0.5334(5) 0.088(2) Uani 1 1 d . . .
C32 C 0.3750(7) 0.3067(4) 0.5329(4) 0.082(2) Uani 1 1 d . . .
C33 C 0.2713(7) 0.2602(4) 0.5010(4) 0.0660(17) Uani 1 1 d . . .
C34 C 0.2672(5) 0.1895(3) 0.4691(3) 0.0565(14) Uani 1 1 d . . .
N5 N 0.0664(5) 0.2389(3) 0.1882(3) 0.0740(14) Uani 1 1 d . . .
C35 C -0.0328(10) 0.2482(8) 0.1038(5) 0.204(7) Uani 1 1 d . . .
H35A H 0.0088 0.2596 0.0777 0.245 Uiso 1 1 calc R . .
H35B H -0.0847 0.2921 0.0969 0.245 Uiso 1 1 calc R . .
C36 C -0.1185(15) 0.1844(11) 0.0631(7) 0.311(12) Uani 1 1 d . . .
H36A H -0.1287 0.1571 0.0996 0.467 Uiso 1 1 calc R . .
H36B H -0.0827 0.1511 0.0436 0.467 Uiso 1 1 calc R . .
H36C H -0.2012 0.2026 0.0189 0.467 Uiso 1 1 calc R . .
C37 C 0.1364(11) 0.3145(5) 0.2153(7) 0.161(4) Uani 1 1 d . . .
H37A H 0.1730 0.3222 0.1854 0.193 Uiso 1 1 calc R . .
H37B H 0.0708 0.3534 0.1973 0.193 Uiso 1 1 calc R . .
C38 C 0.2346(15) 0.3309(8) 0.2953(9) 0.288(11) Uani 1 1 d . . .
H38A H 0.2024 0.3244 0.3271 0.431 Uiso 1 1 calc R . .
H38B H 0.2630 0.3825 0.2996 0.431 Uiso 1 1 calc R . .
H38C H 0.3060 0.2969 0.3140 0.431 Uiso 1 1 calc R . .
C39 C 0.0050(12) 0.2155(9) 0.2284(6) 0.201(6) Uani 1 1 d . . .
H39A H -0.0198 0.1627 0.2136 0.241 Uiso 1 1 calc R . .
H39B H 0.0739 0.2155 0.2852 0.241 Uiso 1 1 calc R . .
C40 C -0.0947(18) 0.2489(11) 0.2211(12) 0.316(13) Uani 1 1 d . . .
H40A H -0.0649 0.2912 0.2573 0.474 Uiso 1 1 calc R . .
H40B H -0.1376 0.2129 0.2335 0.474 Uiso 1 1 calc R . .
H40C H -0.1541 0.2667 0.1672 0.474 Uiso 1 1 calc R . .
C41 C 0.1656(13) 0.1800(6) 0.2093(12) 0.280(11) Uani 1 1 d . . .
H41A H 0.2146 0.1775 0.2672 0.336 Uiso 1 1 calc R . .
H41B H 0.1155 0.1334 0.1902 0.336 Uiso 1 1 calc R . .
C42 C 0.2482(13) 0.1689(10) 0.1974(10) 0.303(12) Uani 1 1 d . . .
H42A H 0.2280 0.1982 0.1520 0.455 Uiso 1 1 calc R . .
H42B H 0.2501 0.1158 0.1872 0.455 Uiso 1 1 calc R . .
H42C H 0.3311 0.1841 0.2437 0.455 Uiso 1 1 calc R . .
H3 H -0.018(5) 0.087(3) 0.537(3) 0.053(14) Uiso 1 1 d . . .
H4 H -0.199(6) 0.062(4) 0.545(4) 0.11(2) Uiso 1 1 d . . .
H5 H -0.392(5) 0.024(3) 0.434(3) 0.054(15) Uiso 1 1 d . . .
H6 H -0.430(7) 0.017(4) 0.309(4) 0.11(2) Uiso 1 1 d . . .
H13 H -0.471(6) 0.071(3) -0.056(3) 0.08(2) Uiso 1 1 d . . .
H14 H -0.494(6) 0.072(3) -0.175(4) 0.09(2) Uiso 1 1 d . . .
H15 H -0.311(5) 0.014(3) -0.178(3) 0.075(16) Uiso 1 1 d . . .
H16 H -0.130(5) -0.040(2) -0.056(3) 0.042(12) Uiso 1 1 d . . .
H20 H 0.096(5) -0.219(3) 0.089(3) 0.069(16) Uiso 1 1 d . . .
H21 H 0.287(6) -0.299(4) 0.135(4) 0.11(2) Uiso 1 1 d . . .
H22 H 0.476(6) -0.273(3) 0.265(3) 0.07(2) Uiso 1 1 d . . .
H23 H 0.511(6) -0.171(3) 0.338(3) 0.080(19) Uiso 1 1 d . . .
H30 H 0.554(6) 0.198(3) 0.497(3) 0.10(2) Uiso 1 1 d . . .
H31 H 0.557(6) 0.313(3) 0.554(3) 0.081(19) Uiso 1 1 d . . .
H32 H 0.374(5) 0.351(3) 0.558(3) 0.08(2) Uiso 1 1 d . . .
H33 H 0.212(5) 0.273(3) 0.504(3) 0.047(16) Uiso 1 1 d . . .
HN1 H -0.038(6) 0.073(3) 0.367(3) 0.07(2) Uiso 1 1 d . . .
HN2 H 0.161(6) 0.100(3) 0.406(4) 0.09(2) Uiso 1 1 d . . .
HN3 H 0.096(5) -0.083(3) 0.194(3) 0.05(2) Uiso 1 1 d . . .
HN4 H -0.084(6) -0.027(3) 0.123(4) 0.08(2) Uiso 1 1 d . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C1 1.218(6) . ?
O2 C18 1.217(6) . ?
N1 C1 1.386(7) . ?
N1 C2 1.403(7) . ?
N1 HN1 0.78(6) . ?
N2 C1 1.364(7) . ?
N2 C34 1.419(7) . ?
N2 HN2 0.93(6) . ?
N3 C18 1.371(7) . ?
N3 C19 1.382(7) . ?
N3 HN3 0.70(5) . ?
N4 C18 1.381(7) . ?
N4 C17 1.399(7) . ?
N4 HN4 0.79(6) . ?
C2 C7 1.385(7) . ?
C2 C3 1.390(7) . ?
C3 C4 1.387(8) . ?
C3 H3 0.99(5) . ?
C4 C5 1.362(9) . ?
C4 H4 0.97(7) . ?
C5 C6 1.364(9) . ?
C5 H5 0.93(5) . ?
C6 C7 1.397(8) . ?
C6 H6 0.98(7) . ?
C7 C8 1.424(8) . ?
C8 C9 1.192(8) . ?
C9 C10 1.393(9) . ?
C10 C11 1.188(8) . ?
C11 C12 1.434(8) . ?
C12 C13 1.398(8) . ?
C12 C17 1.399(8) . ?
C13 C14 1.373(9) . ?
C13 H13 0.93(6) . ?
C14 C15 1.362(9) . ?
C14 H14 0.96(6) . ?
C15 C16 1.405(8) . ?
C15 H15 1.04(5) . ?
C16 C17 1.420(7) . ?
C19 C24 1.408(7) . ?
C19 C20 1.414(8) . ?
C20 C21 1.376(9) . ?
C20 H20 1.10(5) . ?
C21 C22 1.343(10) . ?
C21 H21 0.97(7) . ?
C22 C23 1.386(9) . ?
C22 H22 0.81(5) . ?
C23 C24 1.393(8) . ?
C23 H23 0.98(6) . ?
C24 C25 1.418(8) . ?
C25 C26 1.205(8) . ?
C26 C27 1.370(9) . ?
C27 C28 1.216(8) . ?
C28 C29 1.414(8) . ?
C29 C34 1.385(8) . ?
C29 C30 1.411(8) . ?
C30 C31 1.378(9) . ?
C30 H30 1.06(7) . ?
C31 C32 1.366(10) . ?
C31 H31 0.95(6) . ?
C32 C33 1.352(9) . ?
C32 H32 0.94(6) . ?
C33 C34 1.391(8) . ?
C33 H33 0.83(5) . ?
N5 C35 1.442(9) . ?
N5 C41 1.487(12) . ?
N5 C39 1.486(11) . ?
N5 C37 1.513(10) . ?
C35 C36 1.442(14) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 C38 1.399(14) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C37 H16 1.30(4) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.324(17) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.224(18) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C1 N1 C2 126.2(5) . . ?
C1 N1 HN1 118(4) . . ?
C2 N1 HN1 116(4) . . ?
C1 N2 C34 125.2(5) . . ?
C1 N2 HN2 118(4) . . ?
C34 N2 HN2 114(4) . . ?
C18 N3 C19 126.7(6) . . ?
C18 N3 HN3 112(5) . . ?
C19 N3 HN3 121(5) . . ?
C18 N4 C17 125.2(5) . . ?
C18 N4 HN4 116(5) . . ?
C17 N4 HN4 118(5) . . ?
O1 C1 N2 124.1(5) . . ?
O1 C1 N1 122.6(5) . . ?
N2 C1 N1 113.3(5) . . ?
C7 C2 C3 119.5(5) . . ?
C7 C2 N1 118.6(5) . . ?
C3 C2 N1 121.9(5) . . ?
C4 C3 C2 119.9(6) . . ?
C4 C3 H3 123(3) . . ?
C2 C3 H3 118(3) . . ?
C5 C4 C3 120.1(6) . . ?
C5 C4 H4 117(4) . . ?
C3 C4 H4 122(4) . . ?
C4 C5 C6 120.9(7) . . ?
C4 C5 H5 121(3) . . ?
C6 C5 H5 118(3) . . ?
C5 C6 C7 120.0(6) . . ?
C5 C6 H6 122(4) . . ?
C7 C6 H6 117(4) . . ?
C2 C7 C6 119.6(6) . . ?
C2 C7 C8 120.6(5) . . ?
C6 C7 C8 119.8(6) . . ?
C9 C8 C7 175.9(6) . . ?
C8 C9 C10 176.2(7) . . ?
C11 C10 C9 177.8(6) . . ?
C10 C11 C12 178.3(7) . . ?
C13 C12 C17 119.8(6) . . ?
C13 C12 C11 118.5(6) . . ?
C17 C12 C11 121.8(5) . . ?
C14 C13 C12 120.9(7) . . ?
C14 C13 H13 127(4) . . ?
C12 C13 H13 112(4) . . ?
C15 C14 C13 119.2(7) . . ?
C15 C14 H14 130(4) . . ?
C13 C14 H14 111(4) . . ?
C14 C15 C16 123.3(6) . . ?
C14 C15 H15 125(3) . . ?
C16 C15 H15 111(3) . . ?
C15 C16 C17 116.9(6) . . ?
C12 C17 N4 119.5(5) . . ?
C12 C17 C16 119.9(5) . . ?
N4 C17 C16 120.5(6) . . ?
O2 C18 N3 122.8(6) . . ?
O2 C18 N4 123.1(5) . . ?
N3 C18 N4 114.2(5) . . ?
N3 C19 C24 119.7(5) . . ?
N3 C19 C20 122.4(6) . . ?
C24 C19 C20 117.9(6) . . ?
C21 C20 C19 120.0(7) . . ?
C21 C20 H20 127(3) . . ?
C19 C20 H20 113(3) . . ?
C22 C21 C20 121.7(8) . . ?
C22 C21 H21 123(4) . . ?
C20 C21 H21 115(4) . . ?
C21 C22 C23 120.4(8) . . ?
C21 C22 H22 129(4) . . ?
C23 C22 H22 111(4) . . ?
C22 C23 C24 119.8(7) . . ?
C22 C23 H23 122(3) . . ?
C24 C23 H23 117(3) . . ?
C23 C24 C19 120.1(6) . . ?
C23 C24 C25 119.4(5) . . ?
C19 C24 C25 120.4(5) . . ?
C26 C25 C24 178.5(6) . . ?
C25 C26 C27 177.0(6) . . ?
C28 C27 C26 177.2(6) . . ?
C27 C28 C29 176.3(6) . . ?
C34 C29 C30 119.5(5) . . ?
C34 C29 C28 120.6(5) . . ?
C30 C29 C28 119.9(6) . . ?
C31 C30 C29 119.8(6) . . ?
C31 C30 H30 124(3) . . ?
C29 C30 H30 116(3) . . ?
C32 C31 C30 120.0(7) . . ?
C32 C31 H31 128(4) . . ?
C30 C31 H31 112(4) . . ?
C33 C32 C31 120.5(7) . . ?
C33 C32 H32 116(4) . . ?
C31 C32 H32 123(4) . . ?
C32 C33 C34 121.7(7) . . ?
C32 C33 H33 118(4) . . ?
C34 C33 H33 120(4) . . ?
C29 C34 C33 118.4(6) . . ?
C29 C34 N2 118.9(5) . . ?
C33 C34 N2 122.6(6) . . ?
C35 N5 C41 115.5(11) . . ?
C35 N5 C39 108.9(7) . . ?
C41 N5 C39 106.0(10) . . ?
C35 N5 C37 105.0(7) . . ?
C41 N5 C37 106.5(7) . . ?
C39 N5 C37 115.1(9) . . ?
N5 C35 C36 116.6(10) . . ?
N5 C35 H35A 108.1 . . ?
C36 C35 H35A 108.1 . . ?
N5 C35 H35B 108.1 . . ?
C36 C35 H35B 108.1 . . ?
H35A C35 H35B 107.3 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 N5 123.0(12) . . ?
C38 C37 H37A 106.6 . . ?
N5 C37 H37A 106.6 . . ?
C38 C37 H37B 106.6 . . ?
N5 C37 H37B 106.6 . . ?
H37A C37 H37B 106.5 . . ?
C38 C37 H16 73(2) . . ?
N5 C37 H16 137(2) . . ?
H37A C37 H16 35.6 . . ?
H37B C37 H16 104.9 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 N5 126.4(14) . . ?
C40 C39 H39A 105.7 . . ?
N5 C39 H39A 105.7 . . ?
C40 C39 H39B 105.7 . . ?
N5 C39 H39B 105.7 . . ?
H39A C39 H39B 106.2 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 N5 137.1(18) . . ?
C42 C41 H41A 102.8 . . ?
N5 C41 H41A 102.8 . . ?
C42 C41 H41B 102.8 . . ?
N5 C41 H41B 102.8 . . ?
H41A C41 H41B 105.0 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C34 N2 C1 O1 -3.1(9) . . . . ?
C34 N2 C1 N1 175.0(5) . . . . ?
C2 N1 C1 O1 -6.4(9) . . . . ?
C2 N1 C1 N2 175.4(5) . . . . ?
C1 N1 C2 C7 154.4(5) . . . . ?
C1 N1 C2 C3 -25.9(9) . . . . ?
C7 C2 C3 C4 -0.5(9) . . . . ?
N1 C2 C3 C4 179.9(6) . . . . ?
C2 C3 C4 C5 0.7(10) . . . . ?
C3 C4 C5 C6 1.1(11) . . . . ?
C4 C5 C6 C7 -3.2(11) . . . . ?
C3 C2 C7 C6 -1.6(9) . . . . ?
N1 C2 C7 C6 178.1(6) . . . . ?
C3 C2 C7 C8 -180.0(5) . . . . ?
N1 C2 C7 C8 -0.3(8) . . . . ?
C5 C6 C7 C2 3.4(10) . . . . ?
C5 C6 C7 C8 -178.2(6) . . . . ?
C2 C7 C8 C9 26(10) . . . . ?
C6 C7 C8 C9 -152(10) . . . . ?
C7 C8 C9 C10 44(18) . . . . ?
C8 C9 C10 C11 -33(25) . . . . ?
C9 C10 C11 C12 -93(30) . . . . ?
C10 C11 C12 C13 -79(22) . . . . ?
C10 C11 C12 C17 100(22) . . . . ?
C17 C12 C13 C14 0.1(10) . . . . ?
C11 C12 C13 C14 179.4(6) . . . . ?
C12 C13 C14 C15 0.9(11) . . . . ?
C13 C14 C15 C16 -1.8(11) . . . . ?
C14 C15 C16 C17 1.6(10) . . . . ?
C13 C12 C17 N4 178.0(5) . . . . ?
C11 C12 C17 N4 -1.3(9) . . . . ?
C13 C12 C17 C16 -0.2(9) . . . . ?
C11 C12 C17 C16 -179.5(5) . . . . ?
C18 N4 C17 C12 162.0(5) . . . . ?
C18 N4 C17 C16 -19.8(9) . . . . ?
C15 C16 C17 C12 -0.6(8) . . . . ?
C15 C16 C17 N4 -178.8(5) . . . . ?
C19 N3 C18 O2 1.5(9) . . . . ?
C19 N3 C18 N4 -179.4(5) . . . . ?
C17 N4 C18 O2 -7.1(9) . . . . ?
C17 N4 C18 N3 173.8(5) . . . . ?
C18 N3 C19 C24 156.8(6) . . . . ?
C18 N3 C19 C20 -22.8(9) . . . . ?
N3 C19 C20 C21 178.7(6) . . . . ?
C24 C19 C20 C21 -0.9(9) . . . . ?
C19 C20 C21 C22 2.4(11) . . . . ?
C20 C21 C22 C23 -2.2(13) . . . . ?
C21 C22 C23 C24 0.5(12) . . . . ?
C22 C23 C24 C19 1.0(10) . . . . ?
C22 C23 C24 C25 -178.6(7) . . . . ?
N3 C19 C24 C23 179.6(6) . . . . ?
C20 C19 C24 C23 -0.8(9) . . . . ?
N3 C19 C24 C25 -0.7(9) . . . . ?
C20 C19 C24 C25 178.9(5) . . . . ?
C23 C24 C25 C26 148(26) . . . . ?
C19 C24 C25 C26 -32(27) . . . . ?
C24 C25 C26 C27 -30(35) . . . . ?
C25 C26 C27 C28 17(22) . . . . ?
C26 C27 C28 C29 15(21) . . . . ?
C27 C28 C29 C34 70(10) . . . . ?
C27 C28 C29 C30 -108(10) . . . . ?
C34 C29 C30 C31 0.0(9) . . . . ?
C28 C29 C30 C31 177.9(6) . . . . ?
C29 C30 C31 C32 -1.0(11) . . . . ?
C30 C31 C32 C33 0.4(11) . . . . ?
C31 C32 C33 C34 1.1(11) . . . . ?
C30 C29 C34 C33 1.5(8) . . . . ?
C28 C29 C34 C33 -176.5(5) . . . . ?
C30 C29 C34 N2 177.7(5) . . . . ?
C28 C29 C34 N2 -0.2(8) . . . . ?
C32 C33 C34 C29 -2.0(9) . . . . ?
C32 C33 C34 N2 -178.2(6) . . . . ?
C1 N2 C34 C29 153.4(5) . . . . ?
C1 N2 C34 C33 -30.5(8) . . . . ?
C41 N5 C35 C36 65.4(15) . . . . ?
C39 N5 C35 C36 -53.8(16) . . . . ?
C37 N5 C35 C36 -177.6(12) . . . . ?
C35 N5 C37 C38 175.4(15) . . . . ?
C41 N5 C37 C38 -61.6(18) . . . . ?
C39 N5 C37 C38 55.6(17) . . . . ?
C35 N5 C39 C40 -50.0(19) . . . . ?
C41 N5 C39 C40 -174.9(16) . . . . ?
C37 N5 C39 C40 67.6(17) . . . . ?
C35 N5 C41 C42 62(2) . . . . ?
C39 N5 C41 C42 -177(2) . . . . ?
C37 N5 C41 C42 -54(3) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.994
_diffrn_reflns_theta_full              25.40
_diffrn_measured_fraction_theta_full   0.994
_refine_diff_density_max    0.326
_refine_diff_density_min   -0.301
_refine_diff_density_rms    0.055

data_4  
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 Dihydroindoloquinolinone 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C15 H10 N2 O' 
_chemical_formula_weight          234.25 
 
loop_ 
 _atom_type_symbol 
 _atom_type_description 
 _atom_type_scat_dispersion_real 
 _atom_type_scat_dispersion_imag 
 _atom_type_scat_source 
 'C'  'C'   0.0033   0.0016 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'H'  'H'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'N'  'N'   0.0061   0.0033 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            monoclinic 
_symmetry_space_group_name_H-M    P21/c 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    11.8302(16) 
_cell_length_b                    7.0980(15) 
_cell_length_c                    13.4700(13) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  102.437(8) 
_cell_angle_gamma                 90.00 
_cell_volume                      1104.5(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.409 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              488 
_exptl_absorpt_coefficient_mu     0.091 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             5062 
_diffrn_reflns_av_R_equivalents   0.0490 
_diffrn_reflns_av_sigmaI/netI     0.0609 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        0 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          3.10 
_diffrn_reflns_theta_max          27.48 
_reflns_number_total              2534 
_reflns_number_gt                 1449 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
 
_refine_ls_structure_factor_coef  Fsqd  
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc  
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0611P)²+0.0071P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          2534 
_refine_ls_number_parameters      203 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0988 
_refine_ls_R_factor_gt            0.0421 
_refine_ls_wR_factor_ref          0.1160 
_refine_ls_wR_factor_gt           0.0978 
_refine_ls_goodness_of_fit_ref    0.985 
_refine_ls_restrained_S_all       0.985 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.35879(10) 0.58642(17) 0.00508(8) 0.0482(3) Uani 1 1 d . . . 
N1 N 0.31285(12) 0.6629(2) 0.33469(10) 0.0444(4) Uani 1 1 d . . . 
N2 N 0.51934(12) 0.5929(2) 0.13211(9) 0.0420(4) Uani 1 1 d . . . 
C1 C 0.20411(15) 0.6732(2) 0.27033(12) 0.0427(4) Uani 1 1 d . . . 
C2 C 0.09828(17) 0.7164(3) 0.29328(16) 0.0568(5) Uani 1 1 d . . . 
C3 C 0.00379(19) 0.7256(3) 0.21400(17) 0.0630(6) Uani 1 1 d . . . 
C4 C 0.01285(18) 0.6894(3) 0.11397(16) 0.0607(5) Uani 1 1 d . . . 
C5 C 0.11809(17) 0.6464(3) 0.09195(14) 0.0517(5) Uani 1 1 d . . . 
C6 C 0.21581(14) 0.6414(2) 0.17026(11) 0.0407(4) Uani 1 1 d . . . 
C7 C 0.40193(15) 0.5977(2) 0.09848(11) 0.0387(4) Uani 1 1 d . . . 
C8 C 0.33750(14) 0.6190(2) 0.17596(11) 0.0372(4) Uani 1 1 d . . . 
C9 C 0.39343(14) 0.6346(2) 0.27706(11) 0.0377(4) Uani 1 1 d . . . 
C10 C 0.51610(14) 0.6254(2) 0.31023(11) 0.0381(4) Uani 1 1 d . . . 
C11 C 0.57806(16) 0.6346(2) 0.41141(12) 0.0460(4) Uani 1 1 d . . . 
C12 C 0.69632(17) 0.6259(3) 0.43417(14) 0.0535(5) Uani 1 1 d . . . 
C13 C 0.75627(18) 0.6101(3) 0.35634(15) 0.0539(5) Uani 1 1 d . . . 
C14 C 0.69872(16) 0.6014(3) 0.25705(14) 0.0473(4) Uani 1 1 d . . . 
C15 C 0.57809(14) 0.6063(2) 0.23260(11) 0.0389(4) Uani 1 1 d . . . 
HN1 H 0.3301(16) 0.709(3) 0.4016(16) 0.072(6) Uiso 1 1 d . . . 
HN2 H 0.5614(16) 0.560(3) 0.0827(14) 0.063(6) Uiso 1 1 d . . . 
H2 H 0.0935(16) 0.735(3) 0.3601(15) 0.062(6) Uiso 1 1 d . . . 
H3 H -0.0714(17) 0.758(3) 0.2266(13) 0.062(6) Uiso 1 1 d . . . 
H4 H -0.0637(15) 0.703(2) 0.0578(13) 0.050(5) Uiso 1 1 d . . . 
H5 H 0.1256(14) 0.619(2) 0.0194(13) 0.052(5) Uiso 1 1 d . . . 
H11 H 0.5354(14) 0.651(2) 0.4666(12) 0.047(5) Uiso 1 1 d . . . 
H12 H 0.7427(14) 0.633(2) 0.5122(13) 0.046(4) Uiso 1 1 d . . . 
H13 H 0.8375(16) 0.604(3) 0.3708(13) 0.059(6) Uiso 1 1 d . . . 
H14 H 0.7402(16) 0.588(3) 0.2035(14) 0.062(6) Uiso 1 1 d . . . 
 
 
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
 
loop_ 
 _geom_bond_atom_site_label_1 
 _geom_bond_atom_site_label_2 
 _geom_bond_distance 
 _geom_bond_site_symmetry_2 
 _geom_bond_publ_flag 
O1 C7 1.2542(18) . ? 
N1 C9 1.368(2) . ? 
N1 C1 1.390(2) . ? 
N1 HN1 0.94(2) . ? 
N2 C7 1.365(2) . ? 
N2 C15 1.385(2) . ? 
N2 HN2 0.94(2) . ? 
C1 C2 1.387(3) . ? 
C1 C6 1.403(2) . ? 
C2 C3 1.371(3) . ? 
C2 H2 0.92(2) . ? 
C3 C4 1.398(3) . ? 
C3 H3 0.97(2) . ? 
C4 C5 1.375(3) . ? 
C4 H4 1.053(16) . ? 
C5 C6 1.387(2) . ? 
C5 H5 1.019(16) . ? 
C6 C8 1.434(2) . ? 
C7 C8 1.427(2) . ? 
C8 C9 1.384(2) . ? 
C9 C10 1.425(2) . ? 
C10 C11 1.403(2) . ? 
C10 C15 1.407(2) . ? 
C11 C12 1.368(3) . ? 
C11 H11 0.991(17) . ? 
C12 C13 1.391(3) . ? 
C12 H12 1.077(17) . ? 
C13 C14 1.365(3) . ? 
C13 H13 0.939(18) . ? 
C14 C15 1.394(2) . ? 
C14 H14 0.961(19) . ? 
 
loop_ 
 _geom_angle_atom_site_label_1 
 _geom_angle_atom_site_label_2 
 _geom_angle_atom_site_label_3 
 _geom_angle 
 _geom_angle_site_symmetry_1 
 _geom_angle_site_symmetry_3 
 _geom_angle_publ_flag 
C9 N1 C1 108.56(13) . . ? 
C9 N1 HN1 124.2(12) . . ? 
C1 N1 HN1 124.2(12) . . ? 
C7 N2 C15 125.65(13) . . ? 
C7 N2 HN2 115.2(11) . . ? 
C15 N2 HN2 118.5(11) . . ? 
C2 C1 N1 129.16(16) . . ? 
C2 C1 C6 122.03(17) . . ? 
N1 C1 C6 108.74(14) . . ? 
C3 C2 C1 117.43(18) . . ? 
C3 C2 H2 122.8(12) . . ? 
C1 C2 H2 119.8(12) . . ? 
C2 C3 C4 121.5(2) . . ? 
C2 C3 H3 120.0(11) . . ? 
C4 C3 H3 118.4(11) . . ? 
C5 C4 C3 120.64(19) . . ? 
C5 C4 H4 123.0(9) . . ? 
C3 C4 H4 116.3(9) . . ? 
C4 C5 C6 119.12(17) . . ? 
C4 C5 H5 121.3(10) . . ? 
C6 C5 H5 119.6(10) . . ? 
C5 C6 C1 119.21(16) . . ? 
C5 C6 C8 134.92(15) . . ? 
C1 C6 C8 105.78(14) . . ? 
O1 C7 N2 119.75(14) . . ? 
O1 C7 C8 125.06(16) . . ? 
N2 C7 C8 115.18(14) . . ? 
C9 C8 C7 120.70(15) . . ? 
C9 C8 C6 107.79(13) . . ? 
C7 C8 C6 131.37(14) . . ? 
N1 C9 C8 109.04(14) . . ? 
N1 C9 C10 128.02(14) . . ? 
C8 C9 C10 122.93(14) . . ? 
C11 C10 C15 118.65(16) . . ? 
C11 C10 C9 125.88(15) . . ? 
C15 C10 C9 115.47(14) . . ? 
C12 C11 C10 120.72(16) . . ? 
C12 C11 H11 119.9(9) . . ? 
C10 C11 H11 119.4(9) . . ? 
C11 C12 C13 119.84(17) . . ? 
C11 C12 H12 119.9(9) . . ? 
C13 C12 H12 120.3(9) . . ? 
C14 C13 C12 120.96(18) . . ? 
C14 C13 H13 118.2(11) . . ? 
C12 C13 H13 120.8(11) . . ? 
C13 C14 C15 119.96(17) . . ? 
C13 C14 H14 120.8(11) . . ? 
C15 C14 H14 119.2(11) . . ? 
N2 C15 C14 120.12(14) . . ? 
N2 C15 C10 120.04(15) . . ? 
C14 C15 C10 119.84(15) . . ? 
 
loop_ 
 _geom_torsion_atom_site_label_1 
 _geom_torsion_atom_site_label_2 
 _geom_torsion_atom_site_label_3 
 _geom_torsion_atom_site_label_4 
 _geom_torsion 
 _geom_torsion_site_symmetry_1 
 _geom_torsion_site_symmetry_2 
 _geom_torsion_site_symmetry_3 
 _geom_torsion_site_symmetry_4 
 _geom_torsion_publ_flag 
C9 N1 C1 C2 -173.90(18) . . . . ? 
C9 N1 C1 C6 2.95(19) . . . . ? 
N1 C1 C2 C3 177.00(19) . . . . ? 
C6 C1 C2 C3 0.5(3) . . . . ? 
C1 C2 C3 C4 1.2(3) . . . . ? 
C2 C3 C4 C5 -1.2(3) . . . . ? 
C3 C4 C5 C6 -0.7(3) . . . . ? 
C4 C5 C6 C1 2.4(3) . . . . ? 
C4 C5 C6 C8 -173.65(19) . . . . ? 
C2 C1 C6 C5 -2.3(3) . . . . ? 
N1 C1 C6 C5 -179.47(15) . . . . ? 
C2 C1 C6 C8 174.73(17) . . . . ? 
N1 C1 C6 C8 -2.39(18) . . . . ? 
C15 N2 C7 O1 179.16(15) . . . . ? 
C15 N2 C7 C8 0.1(2) . . . . ? 
O1 C7 C8 C9 -178.51(15) . . . . ? 
N2 C7 C8 C9 0.5(2) . . . . ? 
O1 C7 C8 C6 -3.4(3) . . . . ? 
N2 C7 C8 C6 175.61(16) . . . . ? 
C5 C6 C8 C9 177.39(19) . . . . ? 
C1 C6 C8 C9 0.98(18) . . . . ? 
C5 C6 C8 C7 1.8(3) . . . . ? 
C1 C6 C8 C7 -174.62(17) . . . . ? 
C1 N1 C9 C8 -2.32(19) . . . . ? 
C1 N1 C9 C10 176.32(16) . . . . ? 
C7 C8 C9 N1 176.97(15) . . . . ? 
C6 C8 C9 N1 0.81(18) . . . . ? 
C7 C8 C9 C10 -1.7(2) . . . . ? 
C6 C8 C9 C10 -177.91(15) . . . . ? 
N1 C9 C10 C11 3.5(3) . . . . ? 
C8 C9 C10 C11 -178.01(16) . . . . ? 
N1 C9 C10 C15 -176.20(16) . . . . ? 
C8 C9 C10 C15 2.3(2) . . . . ? 
C15 C10 C11 C12 0.3(2) . . . . ? 
C9 C10 C11 C12 -179.45(16) . . . . ? 
C10 C11 C12 C13 0.8(3) . . . . ? 
C11 C12 C13 C14 -0.6(3) . . . . ? 
C12 C13 C14 C15 -0.7(3) . . . . ? 
C7 N2 C15 C14 -179.34(15) . . . . ? 
C7 N2 C15 C10 0.5(2) . . . . ? 
C13 C14 C15 N2 -178.43(16) . . . . ? 
C13 C14 C15 C10 1.7(3) . . . . ? 
C11 C10 C15 N2 178.64(15) . . . . ? 
C9 C10 C15 N2 -1.6(2) . . . . ? 
C11 C10 C15 C14 -1.5(2) . . . . ? 
C9 C10 C15 C14 178.23(15) . . . . ? 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              27.48 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.136 
_refine_diff_density_min   -0.183 
_refine_diff_density_rms    0.036 
