data_global

_publ_contact_author
;
  Shishkina S.V.
  Institute for Single Crystals
  60 Lenina ave.
  Kharkiv, 61072
  Ukraine
;
_publ_contact_author_phone   '380 57 341 02 58'
_publ_contact_author_fax     '380 57 341 02 73'
_publ_contact_author_email   sveta@xray.isc.kharkov.com

_publ_requested_journal      'test'

_publ_contact_letter
;
 Paper containing this structure has been
submitted to Beilstein Journal of Organic Chemistry.
;

_iucr_compatibility_tag       ACTA95

_publ_section_title
;
 The regioselective synthesis of spirooxindolo pyrrolidines and 
pyrrolizidines via three-component reactions of acrylamides and 
aroylacrylic acids with isatins and ?-amino acids.
;
loop_
 _publ_author_name
    'Pavlovskaya T.L.'
    'Yaremenko F.G.'
    'Lipson V.V.'
    'Shishkina S.V.'
    'Shishkin O.V.'
    'Musatov V.I.'
    'Karpenko A.S.'
    
_publ_section_exptl_prep
;
?
;

data_4a 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C13 H14 Br N3 O2' 
_chemical_formula_sum 
 'C13 H14 Br N3 O2' 
_chemical_formula_weight          324.18 
 
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' 
 'Br'  'Br'  -0.2901   2.4595 
 '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                    6.9659(3) 
_cell_length_b                    7.5441(4) 
_cell_length_c                    13.4092(5) 
_cell_angle_alpha                 90.994(4) 
_cell_angle_beta                  90.947(4) 
_cell_angle_gamma                 106.218(5) 
_cell_volume                      676.36(5) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     273(2) 
_cell_measurement_reflns_used     1901 
_cell_measurement_theta_min       3.0 
_cell_measurement_theta_max       31.9 
 
_exptl_crystal_description        stick 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.592 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              328 
_exptl_absorpt_coefficient_mu     3.040 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.5815 
_exptl_absorpt_correction_T_max   0.7508 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       273(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Enhance (Mo) X-ray Source' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   "Xcalibur"3" 
_diffrn_measurement_method        'ω-scans'  
_diffrn_detector_area_resol_mean  16.1827 
_diffrn_standards_number          2 
_diffrn_standards_interval_count  50 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             6331 
_diffrn_reflns_av_R_equivalents   0.0177 
_diffrn_reflns_av_sigmaI/netI     0.0352 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        18 
_diffrn_reflns_theta_min          3.04 
_diffrn_reflns_theta_max          30.00 
_reflns_number_total              3908 
_reflns_number_gt                 2795 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection         
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr  1 2005,17:53:34)
;         
_computing_cell_refinement         
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr  1 2005,17:53:34)
;
_computing_data_reduction          
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.27p5 beta (release 01-04-2005 CrysAlis171 .NET)
(compiled Apr  1 2005,17:53:34)
;
_computing_structure_solution     'SHELXTL (Sheldrick, 1998)' 
_computing_structure_refinement   'SHELXTL (Sheldrick, 1998)' 
_computing_molecular_graphics     'XP (Siemens, 1998)' 
_computing_publication_material   'SHELXTL (Sheldrick, 1998)' 
 
_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)+(0.0404P)²+0.4820P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    difmap 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3908 
_refine_ls_number_parameters      185 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0728 
_refine_ls_R_factor_gt            0.0464 
_refine_ls_wR_factor_ref          0.1110 
_refine_ls_wR_factor_gt           0.1022 
_refine_ls_goodness_of_fit_ref    1.049 
_refine_ls_restrained_S_all       1.049 
_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 0.74464(5) 0.20917(6) 0.46647(2) 0.07075(16) Uani 1 1 d . . . 
O1 O 0.2709(3) 0.5141(3) 0.92761(16) 0.0515(5) Uani 1 1 d . . . 
O2 O 0.6324(3) 0.0073(2) 0.81685(15) 0.0404(4) Uani 1 1 d . . . 
N1 N 0.4814(4) 0.6233(3) 0.7986(2) 0.0443(6) Uani 1 1 d . . . 
H1N H 0.511(5) 0.722(5) 0.815(3) 0.048(9) Uiso 1 1 d . . . 
N2 N 0.1557(3) 0.1915(3) 0.78855(15) 0.0305(4) Uani 1 1 d . . . 
N3 N 0.7985(3) 0.2751(3) 0.89181(18) 0.0355(5) Uani 1 1 d . . . 
H3NB H 0.790(5) 0.347(5) 0.928(3) 0.045(9) Uiso 1 1 d . . . 
H3NA H 0.911(5) 0.264(4) 0.875(2) 0.046(8) Uiso 1 1 d . . . 
C1 C 0.5591(4) 0.5481(3) 0.7179(2) 0.0373(5) Uani 1 1 d . . . 
C2 C 0.6787(4) 0.6402(4) 0.6436(2) 0.0507(7) Uani 1 1 d . . . 
H2 H 0.7230 0.7685 0.6440 0.061 Uiso 1 1 calc R . . 
C3 C 0.7306(4) 0.5358(5) 0.5687(2) 0.0543(8) Uani 1 1 d . . . 
H3 H 0.8099 0.5941 0.5171 0.065 Uiso 1 1 calc R . . 
C4 C 0.6662(4) 0.3469(4) 0.5699(2) 0.0441(6) Uani 1 1 d . . . 
C5 C 0.5495(3) 0.2530(4) 0.64584(18) 0.0339(5) Uani 1 1 d . . . 
H5 H 0.5090 0.1247 0.6462 0.041 Uiso 1 1 calc R . . 
C6 C 0.4956(3) 0.3564(3) 0.72082(17) 0.0292(4) Uani 1 1 d . . . 
C7 C 0.3632(3) 0.3007(3) 0.81019(16) 0.0262(4) Uani 1 1 d . . . 
C8 C 0.3629(4) 0.4917(3) 0.8548(2) 0.0353(5) Uani 1 1 d . . . 
C9 C 0.4372(3) 0.1882(3) 0.89264(17) 0.0296(5) Uani 1 1 d . . . 
H9 H 0.4576 0.2589 0.9558 0.035 Uiso 1 1 calc R . . 
C10 C 0.2623(4) 0.0125(4) 0.9028(2) 0.0420(6) Uani 1 1 d . . . 
H10B H 0.3111 -0.0951 0.9104 0.050 Uiso 1 1 calc R . . 
H10A H 0.1821 0.0233 0.9598 0.050 Uiso 1 1 calc R . . 
C11 C 0.1431(4) -0.0011(3) 0.8075(2) 0.0411(6) Uani 1 1 d . . . 
H11B H 0.2015 -0.0553 0.7539 0.049 Uiso 1 1 calc R . . 
H11A H 0.0057 -0.0736 0.8155 0.049 Uiso 1 1 calc R . . 
C12 C 0.0704(4) 0.2226(5) 0.6931(2) 0.0488(7) Uani 1 1 d . . . 
H12C H 0.0892 0.3526 0.6853 0.073 Uiso 1 1 calc R . . 
H12B H -0.0699 0.1596 0.6907 0.073 Uiso 1 1 calc R . . 
H12A H 0.1356 0.1763 0.6403 0.073 Uiso 1 1 calc R . . 
C13 C 0.6316(3) 0.1479(3) 0.86433(17) 0.0283(4) Uani 1 1 d . . . 
 
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
Br1 0.04823(19) 0.1142(3) 0.04170(18) -0.01941(18) 0.01531(13) 0.00972(18) 
O1 0.0596(12) 0.0460(11) 0.0527(12) -0.0156(9) 0.0119(10) 0.0214(9) 
O2 0.0386(9) 0.0269(8) 0.0557(11) -0.0058(8) 0.0086(8) 0.0089(7) 
N1 0.0506(13) 0.0233(11) 0.0558(15) -0.0032(10) 0.0031(11) 0.0048(9) 
N2 0.0237(8) 0.0349(10) 0.0310(10) -0.0020(8) 0.0008(7) 0.0049(7) 
N3 0.0306(10) 0.0359(11) 0.0401(12) -0.0068(9) 0.0005(9) 0.0098(9) 
C1 0.0344(12) 0.0328(12) 0.0409(13) 0.0042(10) -0.0010(10) 0.0028(10) 
C2 0.0465(15) 0.0421(15) 0.0533(17) 0.0162(13) 0.0003(13) -0.0052(12) 
C3 0.0387(14) 0.073(2) 0.0399(15) 0.0186(14) 0.0073(12) -0.0038(14) 
C4 0.0302(11) 0.0662(18) 0.0307(12) -0.0006(12) 0.0033(10) 0.0046(12) 
C5 0.0289(10) 0.0416(13) 0.0293(11) -0.0003(10) 0.0033(9) 0.0065(10) 
C6 0.0256(10) 0.0311(11) 0.0291(11) 0.0021(9) 0.0022(8) 0.0048(8) 
C7 0.0259(9) 0.0251(10) 0.0277(10) -0.0024(8) 0.0030(8) 0.0070(8) 
C8 0.0349(11) 0.0307(12) 0.0417(13) -0.0060(10) -0.0005(10) 0.0119(10) 
C9 0.0293(10) 0.0344(11) 0.0268(10) 0.0013(9) 0.0048(8) 0.0115(9) 
C10 0.0358(12) 0.0409(14) 0.0507(15) 0.0156(12) 0.0154(11) 0.0112(11) 
C11 0.0307(11) 0.0320(12) 0.0557(16) -0.0030(11) 0.0084(11) 0.0005(10) 
C12 0.0316(12) 0.073(2) 0.0393(14) 0.0054(14) -0.0036(11) 0.0110(13) 
C13 0.0295(10) 0.0282(11) 0.0279(10) 0.0045(8) 0.0030(8) 0.0088(8) 
 
_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 
Br1 C4 1.895(3) . ? 
O1 C8 1.211(3) . ? 
O2 C13 1.230(3) . ? 
N1 C8 1.351(4) . ? 
N1 C1 1.398(4) . ? 
N2 C12 1.452(3) . ? 
N2 C11 1.458(3) . ? 
N2 C7 1.471(3) . ? 
N3 C13 1.326(3) . ? 
C1 C2 1.378(4) . ? 
C1 C6 1.390(3) . ? 
C2 C3 1.380(5) . ? 
C3 C4 1.370(5) . ? 
C4 C5 1.390(3) . ? 
C5 C6 1.382(3) . ? 
C6 C7 1.517(3) . ? 
C7 C8 1.551(3) . ? 
C7 C9 1.570(3) . ? 
C9 C13 1.521(3) . ? 
C9 C10 1.539(3) . ? 
C10 C11 1.499(4) . ? 
 
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 
C8 N1 C1 112.1(2) . . ? 
C12 N2 C11 114.6(2) . . ? 
C12 N2 C7 116.22(19) . . ? 
C11 N2 C7 107.49(18) . . ? 
C2 C1 C6 122.3(3) . . ? 
C2 C1 N1 128.1(3) . . ? 
C6 C1 N1 109.6(2) . . ? 
C1 C2 C3 117.8(3) . . ? 
C4 C3 C2 120.5(2) . . ? 
C3 C4 C5 122.0(3) . . ? 
C3 C4 Br1 119.0(2) . . ? 
C5 C4 Br1 119.0(2) . . ? 
C6 C5 C4 117.9(2) . . ? 
C5 C6 C1 119.5(2) . . ? 
C5 C6 C7 131.7(2) . . ? 
C1 C6 C7 108.7(2) . . ? 
N2 C7 C6 116.31(18) . . ? 
N2 C7 C8 109.08(18) . . ? 
C6 C7 C8 101.46(18) . . ? 
N2 C7 C9 103.78(17) . . ? 
C6 C7 C9 116.98(18) . . ? 
C8 C7 C9 109.02(18) . . ? 
O1 C8 N1 127.4(2) . . ? 
O1 C8 C7 124.6(2) . . ? 
N1 C8 C7 108.0(2) . . ? 
C13 C9 C10 113.1(2) . . ? 
C13 C9 C7 111.60(17) . . ? 
C10 C9 C7 104.33(19) . . ? 
C11 C10 C9 104.5(2) . . ? 
N2 C11 C10 102.5(2) . . ? 
O2 C13 N3 122.4(2) . . ? 
O2 C13 C9 121.5(2) . . ? 
N3 C13 C9 116.1(2) . . ? 
 
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 
C8 N1 C1 C2 177.4(3) . . . . ? 
C8 N1 C1 C6 -1.9(3) . . . . ? 
C6 C1 C2 C3 1.9(4) . . . . ? 
N1 C1 C2 C3 -177.3(3) . . . . ? 
C1 C2 C3 C4 -0.8(5) . . . . ? 
C2 C3 C4 C5 -0.8(4) . . . . ? 
C2 C3 C4 Br1 -179.1(2) . . . . ? 
C3 C4 C5 C6 1.2(4) . . . . ? 
Br1 C4 C5 C6 179.47(18) . . . . ? 
C4 C5 C6 C1 -0.1(4) . . . . ? 
C4 C5 C6 C7 176.3(2) . . . . ? 
C2 C1 C6 C5 -1.5(4) . . . . ? 
N1 C1 C6 C5 177.9(2) . . . . ? 
C2 C1 C6 C7 -178.7(2) . . . . ? 
N1 C1 C6 C7 0.7(3) . . . . ? 
C12 N2 C7 C6 -29.2(3) . . . . ? 
C11 N2 C7 C6 100.8(2) . . . . ? 
C12 N2 C7 C8 84.8(3) . . . . ? 
C11 N2 C7 C8 -145.3(2) . . . . ? 
C12 N2 C7 C9 -159.1(2) . . . . ? 
C11 N2 C7 C9 -29.2(2) . . . . ? 
C5 C6 C7 N2 -58.0(3) . . . . ? 
C1 C6 C7 N2 118.7(2) . . . . ? 
C5 C6 C7 C8 -176.2(3) . . . . ? 
C1 C6 C7 C8 0.5(2) . . . . ? 
C5 C6 C7 C9 65.4(3) . . . . ? 
C1 C6 C7 C9 -117.9(2) . . . . ? 
C1 N1 C8 O1 -177.9(3) . . . . ? 
C1 N1 C8 C7 2.2(3) . . . . ? 
N2 C7 C8 O1 55.2(3) . . . . ? 
C6 C7 C8 O1 178.5(3) . . . . ? 
C9 C7 C8 O1 -57.5(3) . . . . ? 
N2 C7 C8 N1 -124.9(2) . . . . ? 
C6 C7 C8 N1 -1.6(3) . . . . ? 
C9 C7 C8 N1 122.4(2) . . . . ? 
N2 C7 C9 C13 127.19(19) . . . . ? 
C6 C7 C9 C13 -2.4(3) . . . . ? 
C8 C7 C9 C13 -116.7(2) . . . . ? 
N2 C7 C9 C10 4.7(2) . . . . ? 
C6 C7 C9 C10 -124.9(2) . . . . ? 
C8 C7 C9 C10 120.8(2) . . . . ? 
C13 C9 C10 C11 -101.3(2) . . . . ? 
C7 C9 C10 C11 20.1(2) . . . . ? 
C12 N2 C11 C10 173.4(2) . . . . ? 
C7 N2 C11 C10 42.6(2) . . . . ? 
C9 C10 C11 N2 -37.8(2) . . . . ? 
C10 C9 C13 O2 27.3(3) . . . . ? 
C7 C9 C13 O2 -89.9(3) . . . . ? 
C10 C9 C13 N3 -154.2(2) . . . . ? 
C7 C9 C13 N3 88.5(2) . . . . ? 
 
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 H1N O2  0.74(3) 2.08(3) 2.797(3) 163(4) 1_565 
N3 H3NA N2  0.85(3) 2.26(4) 3.077(3) 163(3) 1_655 
N3 H3NB O1  0.74(3) 2.28(4) 2.994(3) 161(3) 2_667 
 
_diffrn_measured_fraction_theta_max    0.990 
_diffrn_reflns_theta_full              30.00 
_diffrn_measured_fraction_theta_full   0.990 
_refine_diff_density_max    1.041 
_refine_diff_density_min   -1.005 
_refine_diff_density_rms    0.066 
