 
data_compound-7 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C29 H24 N O2 P' 
_chemical_formula_weight          449.46 
 
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' 
 'P'  'P'   0.1023   0.0942 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    P2(1)/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                    9.9427(15) 
_cell_length_b                    16.894(3) 
_cell_length_c                    14.819(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  109.195(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      2350.8(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     273(2) 
_cell_measurement_reflns_used     8410 
_cell_measurement_theta_min       2.41 
_cell_measurement_theta_max       26.09 
 
_exptl_crystal_description        blocks 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.26 
_exptl_crystal_size_mid           0.24 
_exptl_crystal_size_min           0.22 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.270 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              944 
_exptl_absorpt_coefficient_mu     0.143 
_exptl_absorpt_correction_type    empirical 
_exptl_absorpt_correction_T_min   0.96 
_exptl_absorpt_correction_T_max   1.0000 
_exptl_absorpt_process_details    'SADABS, Sheldrick (1996)' 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       273(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   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          'not applicable' 
_diffrn_standards_interval_count  'not applicable' 
_diffrn_standards_interval_time   'not applicable' 
_diffrn_standards_decay_%         none 
_diffrn_reflns_number             12558 
_diffrn_reflns_av_R_equivalents   0.0209 
_diffrn_reflns_av_sigmaI/netI     0.0208 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -20 
_diffrn_reflns_limit_k_max        20 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          1.89 
_diffrn_reflns_theta_max          24.99 
_reflns_number_total              4141 
_reflns_number_gt                 3565 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Bruker SMART' 
_computing_cell_refinement        'Bruker SMART' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
 
_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)+(0.0689P)²+0.3040P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          4141 
_refine_ls_number_parameters      299 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0465 
_refine_ls_R_factor_gt            0.0408 
_refine_ls_wR_factor_ref          0.1140 
_refine_ls_wR_factor_gt           0.1101 
_refine_ls_goodness_of_fit_ref    1.074 
_refine_ls_restrained_S_all       1.074 
_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 
P1 P 0.41438(4) 0.16428(2) 0.13144(3) 0.04009(14) Uani 1 1 d . . . 
O2 O 0.13084(14) 0.30529(7) -0.20278(8) 0.0595(3) Uani 1 1 d . . . 
N1 N 0.16988(13) 0.25807(7) -0.05407(8) 0.0420(3) Uani 1 1 d . . . 
O1 O 0.47740(13) 0.17185(7) 0.05416(8) 0.0551(3) Uani 1 1 d . . . 
C1 C 0.36408(15) 0.06346(9) 0.14460(10) 0.0427(3) Uani 1 1 d . . . 
C13 C 0.25424(15) 0.22575(8) 0.11071(10) 0.0390(3) Uani 1 1 d . . . 
H13 H 0.2151 0.2211 0.1632 0.047 Uiso 1 1 calc R . . 
C19 C 0.23593(16) 0.32755(8) -0.00360(11) 0.0427(3) Uani 1 1 d . . . 
C21 C 0.03203(17) 0.15852(10) -0.00309(11) 0.0487(4) Uani 1 1 d . . . 
H21 H -0.0272 0.1562 -0.0664 0.058 Uiso 1 1 calc R . . 
C20 C 0.14456(15) 0.20472(8) 0.01536(10) 0.0393(3) Uani 1 1 d . . . 
C23 C 0.13665(16) 0.24807(9) -0.15058(10) 0.0449(4) Uani 1 1 d . . . 
C14 C 0.28690(15) 0.31087(9) 0.09404(11) 0.0418(3) Uani 1 1 d . . . 
C24 C 0.11486(17) 0.16701(9) -0.19222(11) 0.0475(4) Uani 1 1 d . . . 
C7 C 0.53862(16) 0.18703(8) 0.24821(11) 0.0435(4) Uani 1 1 d . . . 
C18 C 0.2509(2) 0.40178(10) -0.03823(13) 0.0568(4) Uani 1 1 d . . . 
H18 H 0.2160 0.4129 -0.1033 0.068 Uiso 1 1 calc R . . 
C15 C 0.35456(17) 0.36862(10) 0.15832(12) 0.0531(4) Uani 1 1 d . . . 
H15 H 0.3891 0.3578 0.2235 0.064 Uiso 1 1 calc R . . 
C12 C 0.68266(18) 0.17872(9) 0.25984(14) 0.0560(4) Uani 1 1 d . . . 
H12 H 0.7117 0.1694 0.2072 0.067 Uiso 1 1 calc R . . 
C8 C 0.49858(19) 0.20283(10) 0.32756(12) 0.0520(4) Uani 1 1 d . . . 
H8 H 0.4027 0.2093 0.3203 0.062 Uiso 1 1 calc R . . 
C29 C 0.0169(2) 0.15738(11) -0.28322(12) 0.0585(4) Uani 1 1 d . . . 
H29 H -0.0385 0.2000 -0.3140 0.070 Uiso 1 1 calc R . . 
C9 C 0.5999(2) 0.20919(11) 0.41794(13) 0.0655(5) Uani 1 1 d . . . 
H9 H 0.5722 0.2201 0.4708 0.079 Uiso 1 1 calc R . . 
C4 C 0.31359(19) -0.09479(10) 0.16728(15) 0.0634(5) Uani 1 1 d . . . 
H4 H 0.2975 -0.1481 0.1756 0.076 Uiso 1 1 calc R . . 
C6 C 0.39838(19) 0.00638(10) 0.08880(12) 0.0538(4) Uani 1 1 d . . . 
H6 H 0.4386 0.0216 0.0430 0.065 Uiso 1 1 calc R . . 
C3 C 0.2770(2) -0.03886(11) 0.22227(15) 0.0655(5) Uani 1 1 d . . . 
H3 H 0.2350 -0.0544 0.2670 0.079 Uiso 1 1 calc R . . 
C16 C 0.3703(2) 0.44329(11) 0.12409(15) 0.0661(5) Uani 1 1 d . . . 
H16 H 0.4154 0.4830 0.1668 0.079 Uiso 1 1 calc R . . 
C2 C 0.30239(19) 0.04033(10) 0.21141(13) 0.0563(4) Uani 1 1 d . . . 
H2 H 0.2780 0.0781 0.2490 0.068 Uiso 1 1 calc R . . 
C26 C 0.1828(2) 0.03109(12) -0.19412(15) 0.0711(5) Uani 1 1 d . . . 
H26 H 0.2392 -0.0115 -0.1644 0.085 Uiso 1 1 calc R . . 
C17 C 0.3200(2) 0.45917(10) 0.02775(15) 0.0672(5) Uani 1 1 d . . . 
H17 H 0.3326 0.5095 0.0063 0.081 Uiso 1 1 calc R . . 
C22 C -0.0102(2) 0.10964(12) 0.06684(13) 0.0630(5) Uani 1 1 d . . . 
H22A H 0.0043 0.0547 0.0565 0.094 Uiso 1 1 calc R . . 
H22B H -0.1089 0.1186 0.0585 0.094 Uiso 1 1 calc R . . 
H22C H 0.0467 0.1241 0.1306 0.094 Uiso 1 1 calc R . . 
C28 C 0.0017(2) 0.08472(13) -0.32820(15) 0.0736(6) Uani 1 1 d . . . 
H28 H -0.0644 0.0785 -0.3890 0.088 Uiso 1 1 calc R . . 
C25 C 0.1991(2) 0.10331(11) -0.14842(13) 0.0581(4) Uani 1 1 d . . . 
H25 H 0.2666 0.1093 -0.0881 0.070 Uiso 1 1 calc R . . 
C11 C 0.7826(2) 0.18444(11) 0.35064(17) 0.0715(6) Uani 1 1 d . . . 
H11 H 0.8788 0.1782 0.3588 0.086 Uiso 1 1 calc R . . 
C10 C 0.7405(2) 0.19927(11) 0.42834(16) 0.0715(6) Uani 1 1 d . . . 
H10 H 0.8085 0.2026 0.4888 0.086 Uiso 1 1 calc R . . 
C5 C 0.3737(2) -0.07264(10) 0.10021(14) 0.0644(5) Uani 1 1 d . . . 
H5 H 0.3976 -0.1106 0.0627 0.077 Uiso 1 1 calc R . . 
C27 C 0.0835(3) 0.02173(13) -0.28359(17) 0.0781(6) Uani 1 1 d . . . 
H27 H 0.0719 -0.0273 -0.3137 0.094 Uiso 1 1 calc 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 
P1 O1 1.4805(11) . ? 
P1 C1 1.8038(16) . ? 
P1 C7 1.8062(16) . ? 
P1 C13 1.8402(15) . ? 
O2 C23 1.2277(18) . ? 
N1 C23 1.3683(18) . ? 
N1 C19 1.4302(19) . ? 
N1 C20 1.4508(18) . ? 
C1 C2 1.381(2) . ? 
C1 C6 1.384(2) . ? 
C13 C14 1.512(2) . ? 
C13 C20 1.5161(19) . ? 
C13 H13 0.9800 . ? 
C19 C18 1.381(2) . ? 
C19 C14 1.395(2) . ? 
C21 C20 1.317(2) . ? 
C21 C22 1.490(2) . ? 
C21 H21 0.9300 . ? 
C23 C24 1.488(2) . ? 
C14 C15 1.375(2) . ? 
C24 C25 1.387(2) . ? 
C24 C29 1.389(2) . ? 
C7 C8 1.386(2) . ? 
C7 C12 1.392(2) . ? 
C18 C17 1.388(3) . ? 
C18 H18 0.9300 . ? 
C15 C16 1.388(2) . ? 
C15 H15 0.9300 . ? 
C12 C11 1.389(3) . ? 
C12 H12 0.9300 . ? 
C8 C9 1.391(2) . ? 
C8 H8 0.9300 . ? 
C29 C28 1.381(3) . ? 
C29 H29 0.9300 . ? 
C9 C10 1.365(3) . ? 
C9 H9 0.9300 . ? 
C4 C5 1.369(3) . ? 
C4 C3 1.373(3) . ? 
C4 H4 0.9300 . ? 
C6 C5 1.378(2) . ? 
C6 H6 0.9300 . ? 
C3 C2 1.381(2) . ? 
C3 H3 0.9300 . ? 
C16 C17 1.375(3) . ? 
C16 H16 0.9300 . ? 
C2 H2 0.9300 . ? 
C26 C27 1.377(3) . ? 
C26 C25 1.379(3) . ? 
C26 H26 0.9300 . ? 
C17 H17 0.9300 . ? 
C22 H22A 0.9600 . ? 
C22 H22B 0.9600 . ? 
C22 H22C 0.9600 . ? 
C28 C27 1.370(3) . ? 
C28 H28 0.9300 . ? 
C25 H25 0.9300 . ? 
C11 C10 1.372(3) . ? 
C11 H11 0.9300 . ? 
C10 H10 0.9300 . ? 
C5 H5 0.9300 . ? 
C27 H27 0.9300 . ? 
 
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 P1 C1 111.60(7) . . ? 
O1 P1 C7 113.12(7) . . ? 
C1 P1 C7 102.94(7) . . ? 
O1 P1 C13 112.65(7) . . ? 
C1 P1 C13 107.18(7) . . ? 
C7 P1 C13 108.75(7) . . ? 
C23 N1 C19 124.03(12) . . ? 
C23 N1 C20 128.75(12) . . ? 
C19 N1 C20 107.21(11) . . ? 
C2 C1 C6 119.07(15) . . ? 
C2 C1 P1 123.29(12) . . ? 
C6 C1 P1 117.50(12) . . ? 
C14 C13 C20 101.41(11) . . ? 
C14 C13 P1 110.08(10) . . ? 
C20 C13 P1 109.94(10) . . ? 
C14 C13 H13 111.7 . . ? 
C20 C13 H13 111.7 . . ? 
P1 C13 H13 111.7 . . ? 
C18 C19 C14 121.44(15) . . ? 
C18 C19 N1 129.63(15) . . ? 
C14 C19 N1 108.92(12) . . ? 
C20 C21 C22 126.79(15) . . ? 
C20 C21 H21 116.6 . . ? 
C22 C21 H21 116.6 . . ? 
C21 C20 N1 123.69(13) . . ? 
C21 C20 C13 129.34(13) . . ? 
N1 C20 C13 106.02(11) . . ? 
O2 C23 N1 120.43(14) . . ? 
O2 C23 C24 119.55(13) . . ? 
N1 C23 C24 119.95(13) . . ? 
C15 C14 C19 120.21(14) . . ? 
C15 C14 C13 130.09(14) . . ? 
C19 C14 C13 109.70(13) . . ? 
C25 C24 C29 119.09(16) . . ? 
C25 C24 C23 122.47(15) . . ? 
C29 C24 C23 118.05(15) . . ? 
C8 C7 C12 119.02(16) . . ? 
C8 C7 P1 123.86(12) . . ? 
C12 C7 P1 116.67(13) . . ? 
C19 C18 C17 117.48(16) . . ? 
C19 C18 H18 121.3 . . ? 
C17 C18 H18 121.3 . . ? 
C14 C15 C16 118.70(16) . . ? 
C14 C15 H15 120.7 . . ? 
C16 C15 H15 120.7 . . ? 
C11 C12 C7 119.50(18) . . ? 
C11 C12 H12 120.2 . . ? 
C7 C12 H12 120.2 . . ? 
C7 C8 C9 120.85(17) . . ? 
C7 C8 H8 119.6 . . ? 
C9 C8 H8 119.6 . . ? 
C28 C29 C24 120.22(18) . . ? 
C28 C29 H29 119.9 . . ? 
C24 C29 H29 119.9 . . ? 
C10 C9 C8 119.35(19) . . ? 
C10 C9 H9 120.3 . . ? 
C8 C9 H9 120.3 . . ? 
C5 C4 C3 120.44(17) . . ? 
C5 C4 H4 119.8 . . ? 
C3 C4 H4 119.8 . . ? 
C5 C6 C1 120.85(17) . . ? 
C5 C6 H6 119.6 . . ? 
C1 C6 H6 119.6 . . ? 
C4 C3 C2 120.24(18) . . ? 
C4 C3 H3 119.9 . . ? 
C2 C3 H3 119.9 . . ? 
C17 C16 C15 120.70(17) . . ? 
C17 C16 H16 119.6 . . ? 
C15 C16 H16 119.6 . . ? 
C3 C2 C1 119.92(16) . . ? 
C3 C2 H2 120.0 . . ? 
C1 C2 H2 120.0 . . ? 
C27 C26 C25 120.38(19) . . ? 
C27 C26 H26 119.8 . . ? 
C25 C26 H26 119.8 . . ? 
C16 C17 C18 121.46(17) . . ? 
C16 C17 H17 119.3 . . ? 
C18 C17 H17 119.3 . . ? 
C21 C22 H22A 109.5 . . ? 
C21 C22 H22B 109.5 . . ? 
H22A C22 H22B 109.5 . . ? 
C21 C22 H22C 109.5 . . ? 
H22A C22 H22C 109.5 . . ? 
H22B C22 H22C 109.5 . . ? 
C27 C28 C29 120.25(19) . . ? 
C27 C28 H28 119.9 . . ? 
C29 C28 H28 119.9 . . ? 
C26 C25 C24 120.09(17) . . ? 
C26 C25 H25 120.0 . . ? 
C24 C25 H25 120.0 . . ? 
C10 C11 C12 120.48(18) . . ? 
C10 C11 H11 119.8 . . ? 
C12 C11 H11 119.8 . . ? 
C9 C10 C11 120.77(18) . . ? 
C9 C10 H10 119.6 . . ? 
C11 C10 H10 119.6 . . ? 
C4 C5 C6 119.46(17) . . ? 
C4 C5 H5 120.3 . . ? 
C6 C5 H5 120.3 . . ? 
C28 C27 C26 119.94(19) . . ? 
C28 C27 H27 120.0 . . ? 
C26 C27 H27 120.0 . . ? 
 
_diffrn_measured_fraction_theta_max    1.000 
_diffrn_reflns_theta_full              24.99 
_diffrn_measured_fraction_theta_full   1.000 
_refine_diff_density_max    0.181 
_refine_diff_density_min   -0.315 
_refine_diff_density_rms    0.057 


#===END


data_compound-9 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C22 H20 N O P' 
_chemical_formula_weight          345.36 
 
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' 
 'P'  'P'   0.1023   0.0942 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            Orthorhombic 
_symmetry_space_group_name_H-M    Pccn 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y+1/2, z' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, y-1/2, -z' 
 'x, -y-1/2, z-1/2' 
 '-x-1/2, y, z-1/2' 
 
_cell_length_a                    11.2497(6) 
_cell_length_b                    21.1287(9) 
_cell_length_c                    15.2880(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      3633.8(3) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     3746 
_cell_measurement_theta_min       3.2720 
_cell_measurement_theta_max       28.9440 
 
_exptl_crystal_description        blocks 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.26 
_exptl_crystal_size_mid           0.24 
_exptl_crystal_size_min           0.20 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.263 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1456 
_exptl_absorpt_coefficient_mu     0.160 
_exptl_absorpt_correction_type    empirical 
_exptl_absorpt_correction_T_min   0.9595 
_exptl_absorpt_correction_T_max   0.9687 
_exptl_absorpt_process_details    'CrysAlisPro, Oxford Diffraction Ltd.'  
 
_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   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          'not applicable'
_diffrn_standards_interval_count  'not applicable' 
_diffrn_standards_interval_time   'not applicable' 
_diffrn_standards_decay_%         none
_diffrn_reflns_number             9322 
_diffrn_reflns_av_R_equivalents   0.0218 
_diffrn_reflns_av_sigmaI/netI     0.0223 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -25 
_diffrn_reflns_limit_k_max        23 
_diffrn_reflns_limit_l_min        -18 
_diffrn_reflns_limit_l_max        12 
_diffrn_reflns_theta_min          2.83 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              3205 
_reflns_number_gt                 2672 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'CrysAlisPro, Oxford Diffraction Ltd.' 
_computing_cell_refinement        'CrysAlisPro, Oxford Diffraction Ltd.' 
_computing_data_reduction         'CrysAlisPro, Oxford Diffraction Ltd.'  
_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)+(0.0476P)²+1.9293P] 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          3205 
_refine_ls_number_parameters      231 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0537 
_refine_ls_R_factor_gt            0.0430 
_refine_ls_wR_factor_ref          0.1141 
_refine_ls_wR_factor_gt           0.1076 
_refine_ls_goodness_of_fit_ref    1.085 
_refine_ls_restrained_S_all       1.085 
_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 
P1 P -0.00616(4) 0.38329(2) 0.21269(3) 0.02960(16) Uani 1 1 d . . . 
O1 O -0.06343(12) 0.42401(6) 0.28043(8) 0.0387(3) Uani 1 1 d . . . 
C7 C -0.09583(18) 0.38147(9) 0.11457(12) 0.0339(4) Uani 1 1 d . . . 
N1 N 0.30328(16) 0.46749(9) 0.18054(11) 0.0393(4) Uani 1 1 d . . . 
C13 C 0.13664(17) 0.41007(9) 0.18082(12) 0.0314(4) Uani 1 1 d . . . 
C14 C 0.20814(17) 0.39125(9) 0.10631(12) 0.0337(4) Uani 1 1 d . . . 
C20 C 0.19943(18) 0.45715(9) 0.22374(12) 0.0339(4) Uani 1 1 d . . . 
C19 C 0.31150(18) 0.42863(9) 0.10886(13) 0.0363(5) Uani 1 1 d . . . 
C15 C 0.1957(2) 0.34751(10) 0.03830(14) 0.0449(5) Uani 1 1 d . . . 
H15 H 0.1285 0.3221 0.0346 0.054 Uiso 1 1 calc R . . 
C8 C -0.1880(2) 0.33878(11) 0.10447(15) 0.0488(6) Uani 1 1 d . . . 
H8 H -0.1961 0.3053 0.1435 0.059 Uiso 1 1 calc R . . 
C10 C -0.2574(2) 0.39455(12) -0.02133(15) 0.0545(6) Uani 1 1 d . . . 
H10 H -0.3123 0.3994 -0.0663 0.065 Uiso 1 1 calc R . . 
C1 C 0.00409(17) 0.30324(9) 0.25338(13) 0.0330(4) Uani 1 1 d . . . 
C17 C 0.3862(2) 0.38046(13) -0.01868(16) 0.0564(6) Uani 1 1 d . . . 
H17 H 0.4450 0.3760 -0.0610 0.068 Uiso 1 1 calc R . . 
C21 C 0.1688(2) 0.49830(10) 0.29955(13) 0.0450(5) Uani 1 1 d . . . 
H21A H 0.2397 0.5063 0.3339 0.054 Uiso 1 1 calc R . . 
H21B H 0.1118 0.4767 0.3366 0.054 Uiso 1 1 calc R . . 
C18 C 0.4008(2) 0.42393(11) 0.04670(14) 0.0481(6) Uani 1 1 d . . . 
H18 H 0.4682 0.4494 0.0494 0.058 Uiso 1 1 calc R . . 
C9 C -0.2684(2) 0.34566(12) 0.03635(16) 0.0597(7) Uani 1 1 d . . . 
H9 H -0.3302 0.3168 0.0300 0.072 Uiso 1 1 calc R . . 
C12 C -0.0855(2) 0.42991(11) 0.05442(14) 0.0480(6) Uani 1 1 d . . . 
H12 H -0.0232 0.4586 0.0596 0.058 Uiso 1 1 calc R . . 
C22 C 0.1165(3) 0.56078(11) 0.26902(17) 0.0595(7) Uani 1 1 d . . . 
H22A H 0.1739 0.5829 0.2340 0.089 Uiso 1 1 calc R . . 
H22B H 0.0960 0.5861 0.3189 0.089 Uiso 1 1 calc R . . 
H22C H 0.0464 0.5528 0.2349 0.089 Uiso 1 1 calc R . . 
C6 C 0.0877(3) 0.26041(11) 0.22656(17) 0.0652(8) Uani 1 1 d . . . 
H6 H 0.1398 0.2711 0.1817 0.078 Uiso 1 1 calc R . . 
C16 C 0.2847(2) 0.34273(12) -0.02299(15) 0.0560(6) Uani 1 1 d . . . 
H16 H 0.2770 0.3137 -0.0683 0.067 Uiso 1 1 calc R . . 
C11 C -0.1655(2) 0.43649(12) -0.01308(15) 0.0557(6) Uani 1 1 d . . . 
H11 H -0.1571 0.4694 -0.0530 0.067 Uiso 1 1 calc R . . 
C2 C -0.0718(2) 0.28527(11) 0.31893(16) 0.0603(7) Uani 1 1 d . . . 
H2 H -0.1305 0.3131 0.3377 0.072 Uiso 1 1 calc R . . 
C5 C 0.0959(3) 0.20129(13) 0.2653(2) 0.0797(9) Uani 1 1 d . . . 
H5 H 0.1531 0.1727 0.2462 0.096 Uiso 1 1 calc R . . 
C3 C -0.0622(3) 0.22619(12) 0.35756(18) 0.0752(9) Uani 1 1 d . . . 
H3 H -0.1140 0.2149 0.4024 0.090 Uiso 1 1 calc R . . 
C4 C 0.0216(3) 0.18503(11) 0.33061(18) 0.0634(7) Uani 1 1 d . . . 
H4 H 0.0281 0.1455 0.3570 0.076 Uiso 1 1 calc R . . 
H1D H 0.352(2) 0.4967(11) 0.1941(14) 0.045(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 
P1 O1 1.4926(14) . ? 
P1 C13 1.771(2) . ? 
P1 C1 1.8059(19) . ? 
P1 C7 1.808(2) . ? 
C7 C12 1.381(3) . ? 
C7 C8 1.383(3) . ? 
N1 C20 1.360(3) . ? 
N1 C19 1.372(3) . ? 
N1 H1D 0.85(2) . ? 
C13 C20 1.385(3) . ? 
C13 C14 1.450(3) . ? 
C14 C15 1.398(3) . ? 
C14 C19 1.406(3) . ? 
C20 C21 1.489(3) . ? 
C19 C18 1.387(3) . ? 
C15 C16 1.375(3) . ? 
C15 H15 0.9300 . ? 
C8 C9 1.387(3) . ? 
C8 H8 0.9300 . ? 
C10 C9 1.364(3) . ? 
C10 C11 1.367(3) . ? 
C10 H10 0.9300 . ? 
C1 C6 1.368(3) . ? 
C1 C2 1.370(3) . ? 
C17 C18 1.367(3) . ? 
C17 C16 1.394(3) . ? 
C17 H17 0.9300 . ? 
C21 C22 1.519(3) . ? 
C21 H21A 0.9700 . ? 
C21 H21B 0.9700 . ? 
C18 H18 0.9300 . ? 
C9 H9 0.9300 . ? 
C12 C11 1.377(3) . ? 
C12 H12 0.9300 . ? 
C22 H22A 0.9600 . ? 
C22 H22B 0.9600 . ? 
C22 H22C 0.9600 . ? 
C6 C5 1.386(4) . ? 
C6 H6 0.9300 . ? 
C16 H16 0.9300 . ? 
C11 H11 0.9300 . ? 
C2 C3 1.385(3) . ? 
C2 H2 0.9300 . ? 
C5 C4 1.347(4) . ? 
C5 H5 0.9300 . ? 
C3 C4 1.347(4) . ? 
C3 H3 0.9300 . ? 
C4 H4 0.9300 . ? 
 
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 P1 C13 113.46(9) . . ? 
O1 P1 C1 109.17(9) . . ? 
C13 P1 C1 109.63(9) . . ? 
O1 P1 C7 110.31(8) . . ? 
C13 P1 C7 106.53(9) . . ? 
C1 P1 C7 107.54(9) . . ? 
C12 C7 C8 118.19(19) . . ? 
C12 C7 P1 119.31(16) . . ? 
C8 C7 P1 121.66(16) . . ? 
C20 N1 C19 110.46(17) . . ? 
C20 N1 H1D 123.3(15) . . ? 
C19 N1 H1D 125.9(15) . . ? 
C20 C13 C14 106.62(17) . . ? 
C20 C13 P1 124.16(15) . . ? 
C14 C13 P1 129.16(14) . . ? 
C15 C14 C19 118.32(19) . . ? 
C15 C14 C13 135.24(19) . . ? 
C19 C14 C13 106.43(17) . . ? 
N1 C20 C13 108.87(17) . . ? 
N1 C20 C21 118.88(18) . . ? 
C13 C20 C21 132.05(19) . . ? 
N1 C19 C18 129.7(2) . . ? 
N1 C19 C14 107.61(18) . . ? 
C18 C19 C14 122.69(19) . . ? 
C16 C15 C14 118.9(2) . . ? 
C16 C15 H15 120.6 . . ? 
C14 C15 H15 120.6 . . ? 
C7 C8 C9 120.3(2) . . ? 
C7 C8 H8 119.8 . . ? 
C9 C8 H8 119.8 . . ? 
C9 C10 C11 120.0(2) . . ? 
C9 C10 H10 120.0 . . ? 
C11 C10 H10 120.0 . . ? 
C6 C1 C2 117.7(2) . . ? 
C6 C1 P1 124.06(16) . . ? 
C2 C1 P1 118.14(16) . . ? 
C18 C17 C16 121.2(2) . . ? 
C18 C17 H17 119.4 . . ? 
C16 C17 H17 119.4 . . ? 
C20 C21 C22 110.98(18) . . ? 
C20 C21 H21A 109.4 . . ? 
C22 C21 H21A 109.4 . . ? 
C20 C21 H21B 109.4 . . ? 
C22 C21 H21B 109.4 . . ? 
H21A C21 H21B 108.0 . . ? 
C17 C18 C19 117.5(2) . . ? 
C17 C18 H18 121.3 . . ? 
C19 C18 H18 121.3 . . ? 
C10 C9 C8 120.3(2) . . ? 
C10 C9 H9 119.8 . . ? 
C8 C9 H9 119.8 . . ? 
C11 C12 C7 121.2(2) . . ? 
C11 C12 H12 119.4 . . ? 
C7 C12 H12 119.4 . . ? 
C21 C22 H22A 109.5 . . ? 
C21 C22 H22B 109.5 . . ? 
H22A C22 H22B 109.5 . . ? 
C21 C22 H22C 109.5 . . ? 
H22A C22 H22C 109.5 . . ? 
H22B C22 H22C 109.5 . . ? 
C1 C6 C5 120.9(2) . . ? 
C1 C6 H6 119.5 . . ? 
C5 C6 H6 119.5 . . ? 
C15 C16 C17 121.5(2) . . ? 
C15 C16 H16 119.3 . . ? 
C17 C16 H16 119.3 . . ? 
C10 C11 C12 119.9(2) . . ? 
C10 C11 H11 120.1 . . ? 
C12 C11 H11 120.1 . . ? 
C1 C2 C3 120.9(2) . . ? 
C1 C2 H2 119.6 . . ? 
C3 C2 H2 119.6 . . ? 
C4 C5 C6 120.4(3) . . ? 
C4 C5 H5 119.8 . . ? 
C6 C5 H5 119.8 . . ? 
C4 C3 C2 120.4(2) . . ? 
C4 C3 H3 119.8 . . ? 
C2 C3 H3 119.8 . . ? 
C5 C4 C3 119.8(2) . . ? 
C5 C4 H4 120.1 . . ? 
C3 C4 H4 120.1 . . ? 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.339 
_refine_diff_density_min   -0.296 
_refine_diff_density_rms    0.040 

#===END

 
data_compound-20 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C22 H17 O3 P' 
_chemical_formula_weight          360.33 
 
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' 
 'O'  'O'   0.0106   0.0060 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'P'  'P'   0.1023   0.0942 
 '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                    9.7440(19) 
_cell_length_b                    9.9918(17) 
_cell_length_c                    10.2864(18) 
_cell_angle_alpha                 84.229(14) 
_cell_angle_beta                  76.556(16) 
_cell_angle_gamma                 66.323(18) 
_cell_volume                      892.0(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     298(2) 
_cell_measurement_reflns_used     1632 
_cell_measurement_theta_min       2.8946 
_cell_measurement_theta_max       28.9481 
 
_exptl_crystal_description        blocks 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.22 
_exptl_crystal_size_mid           0.20 
_exptl_crystal_size_min           0.18 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.342 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              376 
_exptl_absorpt_coefficient_mu     0.173 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.94787 
_exptl_absorpt_correction_T_max   1.00000 
_exptl_absorpt_process_details    'CrysAlisPro, Oxford Diffraction Ltd.' 
 
_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   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          'not applicable'
_diffrn_standards_interval_count  'not applicable' 
_diffrn_standards_interval_time   'not applicable' 
_diffrn_standards_decay_%         none 
_diffrn_reflns_number             6130 
_diffrn_reflns_av_R_equivalents   0.0229 
_diffrn_reflns_av_sigmaI/netI     0.0444 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        10 
_diffrn_reflns_limit_k_min        -12 
_diffrn_reflns_limit_k_max        11 
_diffrn_reflns_limit_l_min        -12 
_diffrn_reflns_limit_l_max        8 
_diffrn_reflns_theta_min          2.90 
_diffrn_reflns_theta_max          26.37 
_reflns_number_total              3647 
_reflns_number_gt                 2565 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'CrysAlisPro, Oxford Diffraction Ltd.' 
_computing_cell_refinement        'CrysAlisPro, Oxford Diffraction Ltd.' 
_computing_data_reduction         'CrysAlisPro, Oxford Diffraction Ltd.'  
_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)+(0.0636P)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     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          3647 
_refine_ls_number_parameters      236 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0686 
_refine_ls_R_factor_gt            0.0455 
_refine_ls_wR_factor_ref          0.1191 
_refine_ls_wR_factor_gt           0.1114 
_refine_ls_goodness_of_fit_ref    1.010 
_refine_ls_restrained_S_all       1.010 
_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 
P1 P 0.27438(6) 0.33994(5) 0.36034(5) 0.04064(17) Uani 1 1 d . . . 
O3 O -0.07849(15) 0.56038(13) 0.16580(14) 0.0507(4) Uani 1 1 d . . . 
O1 O 0.23801(17) 0.28108(14) 0.49639(14) 0.0557(4) Uani 1 1 d . . . 
C13 C 0.1156(2) 0.39397(18) 0.27569(19) 0.0391(4) Uani 1 1 d . . . 
O2 O -0.21175(17) 0.49584(16) 0.05784(16) 0.0660(5) Uani 1 1 d . . . 
C19 C -0.0431(2) 0.3081(2) 0.1751(2) 0.0441(5) Uani 1 1 d . . . 
C1 C 0.4313(2) 0.20362(18) 0.25145(19) 0.0390(4) Uani 1 1 d . . . 
C14 C 0.0676(2) 0.27788(19) 0.2523(2) 0.0415(5) Uani 1 1 d . . . 
C7 C 0.3332(2) 0.48801(19) 0.36581(19) 0.0406(4) Uani 1 1 d . . . 
C6 C 0.4641(2) 0.2156(2) 0.1137(2) 0.0494(5) Uani 1 1 d . . . 
H6 H 0.4044 0.2979 0.0716 0.059 Uiso 1 1 calc R . . 
C2 C 0.5207(2) 0.0781(2) 0.3127(2) 0.0517(5) Uani 1 1 d . . . 
H2 H 0.5009 0.0694 0.4054 0.062 Uiso 1 1 calc R . . 
C8 C 0.4333(2) 0.5251(2) 0.2626(2) 0.0494(5) Uani 1 1 d . . . 
H8 H 0.4742 0.4717 0.1839 0.059 Uiso 1 1 calc R . . 
C20 C -0.1173(2) 0.4554(2) 0.1271(2) 0.0479(5) Uani 1 1 d . . . 
C15 C 0.1258(2) 0.1350(2) 0.3049(2) 0.0545(6) Uani 1 1 d . . . 
H15 H 0.1971 0.1107 0.3587 0.065 Uiso 1 1 calc R . . 
C21 C 0.0382(2) 0.53075(19) 0.2335(2) 0.0447(5) Uani 1 1 d . . . 
C9 C 0.4717(2) 0.6410(2) 0.2770(2) 0.0573(6) Uani 1 1 d . . . 
H9 H 0.5373 0.6662 0.2073 0.069 Uiso 1 1 calc R . . 
C3 C 0.6390(2) -0.0340(2) 0.2357(3) 0.0637(7) Uani 1 1 d . . . 
H3 H 0.6963 -0.1186 0.2769 0.076 Uiso 1 1 calc R . . 
C10 C 0.4135(3) 0.7190(2) 0.3939(3) 0.0601(6) Uani 1 1 d . . . 
H10 H 0.4388 0.7974 0.4030 0.072 Uiso 1 1 calc R . . 
C4 C 0.6714(2) -0.0203(2) 0.1003(3) 0.0652(7) Uani 1 1 d . . . 
H4 H 0.7512 -0.0953 0.0492 0.078 Uiso 1 1 calc R . . 
C22 C 0.0512(3) 0.67187(19) 0.2460(3) 0.0617(7) Uani 1 1 d . . . 
H22A H 0.0098 0.7050 0.3367 0.093 Uiso 1 1 calc R . . 
H22B H -0.0048 0.7432 0.1876 0.093 Uiso 1 1 calc R . . 
H22C H 0.1571 0.6586 0.2219 0.093 Uiso 1 1 calc R . . 
C11 C 0.3184(3) 0.6809(2) 0.4965(3) 0.0672(7) Uani 1 1 d . . . 
H11 H 0.2798 0.7329 0.5759 0.081 Uiso 1 1 calc R . . 
C18 C -0.0902(3) 0.2019(2) 0.1479(2) 0.0606(6) Uani 1 1 d . . . 
H18 H -0.1636 0.2250 0.0964 0.073 Uiso 1 1 calc R . . 
C5 C 0.5856(3) 0.1053(2) 0.0384(2) 0.0621(6) Uani 1 1 d . . . 
H5 H 0.6099 0.1154 -0.0540 0.074 Uiso 1 1 calc R . . 
C12 C 0.2793(3) 0.5663(2) 0.4830(2) 0.0567(6) Uani 1 1 d . . . 
H12 H 0.2155 0.5408 0.5541 0.068 Uiso 1 1 calc R . . 
C16 C 0.0774(3) 0.0309(2) 0.2768(3) 0.0704(7) Uani 1 1 d . . . 
H16 H 0.1169 -0.0627 0.3123 0.084 Uiso 1 1 calc R . . 
C17 C -0.0278(3) 0.0622(2) 0.1975(3) 0.0718(7) Uani 1 1 d . . . 
H17 H -0.0565 -0.0104 0.1775 0.086 Uiso 1 1 calc 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 
P1 O1 1.4837(14) . ? 
P1 C7 1.7981(19) . ? 
P1 C1 1.813(2) . ? 
P1 C13 1.8178(19) . ? 
O3 C20 1.369(2) . ? 
O3 C21 1.386(2) . ? 
C13 C21 1.353(2) . ? 
C13 C14 1.472(2) . ? 
O2 C20 1.210(2) . ? 
C19 C18 1.387(3) . ? 
C19 C14 1.405(3) . ? 
C19 C20 1.449(3) . ? 
C1 C6 1.382(3) . ? 
C1 C2 1.396(2) . ? 
C14 C15 1.411(3) . ? 
C7 C12 1.381(3) . ? 
C7 C8 1.395(3) . ? 
C6 C5 1.383(3) . ? 
C6 H6 0.9300 . ? 
C2 C3 1.388(3) . ? 
C2 H2 0.9300 . ? 
C8 C9 1.383(3) . ? 
C8 H8 0.9300 . ? 
C15 C16 1.380(3) . ? 
C15 H15 0.9300 . ? 
C21 C22 1.486(3) . ? 
C9 C10 1.375(3) . ? 
C9 H9 0.9300 . ? 
C3 C4 1.360(3) . ? 
C3 H3 0.9300 . ? 
C10 C11 1.366(3) . ? 
C10 H10 0.9300 . ? 
C4 C5 1.387(3) . ? 
C4 H4 0.9300 . ? 
C22 H22A 0.9600 . ? 
C22 H22B 0.9600 . ? 
C22 H22C 0.9600 . ? 
C11 C12 1.371(3) . ? 
C11 H11 0.9300 . ? 
C18 C17 1.378(3) . ? 
C18 H18 0.9300 . ? 
C5 H5 0.9300 . ? 
C12 H12 0.9300 . ? 
C16 C17 1.376(3) . ? 
C16 H16 0.9300 . ? 
C17 H17 0.9300 . ? 
 
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 P1 C7 110.95(9) . . ? 
O1 P1 C1 112.09(9) . . ? 
C7 P1 C1 106.21(9) . . ? 
O1 P1 C13 111.84(9) . . ? 
C7 P1 C13 111.43(8) . . ? 
C1 P1 C13 103.99(8) . . ? 
C20 O3 C21 123.92(14) . . ? 
C21 C13 C14 117.75(17) . . ? 
C21 C13 P1 125.71(15) . . ? 
C14 C13 P1 116.54(12) . . ? 
C18 C19 C14 121.98(18) . . ? 
C18 C19 C20 118.00(19) . . ? 
C14 C19 C20 119.95(18) . . ? 
C6 C1 C2 119.06(18) . . ? 
C6 C1 P1 124.13(13) . . ? 
C2 C1 P1 116.79(16) . . ? 
C19 C14 C15 116.80(18) . . ? 
C19 C14 C13 119.66(16) . . ? 
C15 C14 C13 123.53(18) . . ? 
C12 C7 C8 118.19(19) . . ? 
C12 C7 P1 117.07(16) . . ? 
C8 C7 P1 124.69(15) . . ? 
C1 C6 C5 120.15(18) . . ? 
C1 C6 H6 119.9 . . ? 
C5 C6 H6 119.9 . . ? 
C3 C2 C1 120.2(2) . . ? 
C3 C2 H2 119.9 . . ? 
C1 C2 H2 119.9 . . ? 
C9 C8 C7 120.2(2) . . ? 
C9 C8 H8 119.9 . . ? 
C7 C8 H8 119.9 . . ? 
O2 C20 O3 116.56(18) . . ? 
O2 C20 C19 126.8(2) . . ? 
O3 C20 C19 116.62(18) . . ? 
C16 C15 C14 120.3(2) . . ? 
C16 C15 H15 119.8 . . ? 
C14 C15 H15 119.8 . . ? 
C13 C21 O3 121.46(17) . . ? 
C13 C21 C22 131.75(19) . . ? 
O3 C21 C22 106.78(15) . . ? 
C10 C9 C8 120.2(2) . . ? 
C10 C9 H9 119.9 . . ? 
C8 C9 H9 119.9 . . ? 
C4 C3 C2 120.19(19) . . ? 
C4 C3 H3 119.9 . . ? 
C2 C3 H3 119.9 . . ? 
C11 C10 C9 119.8(2) . . ? 
C11 C10 H10 120.1 . . ? 
C9 C10 H10 120.1 . . ? 
C3 C4 C5 120.2(2) . . ? 
C3 C4 H4 119.9 . . ? 
C5 C4 H4 119.9 . . ? 
C21 C22 H22A 109.5 . . ? 
C21 C22 H22B 109.5 . . ? 
H22A C22 H22B 109.5 . . ? 
C21 C22 H22C 109.5 . . ? 
H22A C22 H22C 109.5 . . ? 
H22B C22 H22C 109.5 . . ? 
C10 C11 C12 120.3(2) . . ? 
C10 C11 H11 119.8 . . ? 
C12 C11 H11 119.8 . . ? 
C17 C18 C19 119.8(2) . . ? 
C17 C18 H18 120.1 . . ? 
C19 C18 H18 120.1 . . ? 
C6 C5 C4 120.1(2) . . ? 
C6 C5 H5 119.9 . . ? 
C4 C5 H5 119.9 . . ? 
C11 C12 C7 121.2(2) . . ? 
C11 C12 H12 119.4 . . ? 
C7 C12 H12 119.4 . . ? 
C17 C16 C15 121.7(2) . . ? 
C17 C16 H16 119.1 . . ? 
C15 C16 H16 119.1 . . ? 
C16 C17 C18 119.4(2) . . ? 
C16 C17 H17 120.3 . . ? 
C18 C17 H17 120.3 . . ? 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              26.37 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.210 
_refine_diff_density_min   -0.283 
_refine_diff_density_rms    0.052 


#===END

 
data_compound-33 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C11 H9 Br O2' 
_chemical_formula_weight          253.09 
 
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' 
 '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                    7.9413(19) 
_cell_length_b                    7.9674(19) 
_cell_length_c                    9.746(2) 
_cell_angle_alpha                 66.05(2) 
_cell_angle_beta                  79.379(19) 
_cell_angle_gamma                 62.93(2) 
_cell_volume                      501.8(2) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     1262 
_cell_measurement_theta_min       2.8654 
_cell_measurement_theta_max       28.7787 
 
_exptl_crystal_description        needles 
_exptl_crystal_colour             colourless 
_exptl_crystal_size_max           0.18 
_exptl_crystal_size_mid           0.16 
_exptl_crystal_size_min           0.12 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.675 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              252 
_exptl_absorpt_coefficient_mu     4.064 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.44463 
_exptl_absorpt_correction_T_max   1.00000 
_exptl_absorpt_process_details    'CrysAlisPro, Oxford Diffraction Ltd.' 
 
_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   'CCD area detector' 
_diffrn_measurement_method        'phi and omega scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          'not applicable'
_diffrn_standards_interval_count  'not applicable' 
_diffrn_standards_interval_time   'not applicable' 
_diffrn_standards_decay_%         none
_diffrn_reflns_number             1856 
_diffrn_reflns_av_R_equivalents   0.0183 
_diffrn_reflns_av_sigmaI/netI     0.0453 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        5 
_diffrn_reflns_limit_k_min        -9 
_diffrn_reflns_limit_k_max        9 
_diffrn_reflns_limit_l_min        -10 
_diffrn_reflns_limit_l_max        11 
_diffrn_reflns_theta_min          3.09 
_diffrn_reflns_theta_max          24.99 
_reflns_number_total              1354 
_reflns_number_gt                 1155 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'CrysAlisPro, Oxford Diffraction Ltd.' 
_computing_cell_refinement        'CrysAlisPro, Oxford Diffraction Ltd.' 
_computing_data_reduction         'CrysAlisPro, Oxford Diffraction Ltd.'  
_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)+(0.0555P)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     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          1354 
_refine_ls_number_parameters      128 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0513 
_refine_ls_R_factor_gt            0.0425 
_refine_ls_wR_factor_ref          0.1108 
_refine_ls_wR_factor_gt           0.1021 
_refine_ls_goodness_of_fit_ref    1.097 
_refine_ls_restrained_S_all       1.097 
_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 
Br Br 1.29394(7) 0.17180(9) -0.41881(6) 0.0597(3) Uani 1 1 d . . . 
C4 C 1.1885(7) 0.1810(8) -0.2284(7) 0.0401(13) Uani 1 1 d . . . 
O2 O 0.6844(5) 0.5153(6) 0.0584(5) 0.0500(10) Uani 1 1 d . . . 
O1 O 0.6667(5) 0.6591(7) -0.1900(5) 0.0610(11) Uani 1 1 d . . . 
C7 C 0.7562(8) 0.5205(10) -0.0840(7) 0.0459(14) Uani 1 1 d . . . 
C5 C 1.0138(6) 0.3431(8) -0.2271(6) 0.0435(13) Uani 1 1 d . . . 
H5 H 0.9505 0.4423 -0.3155 0.052 Uiso 1 1 calc R . . 
C8 C 0.7774(7) 0.3676(9) 0.1894(6) 0.0435(14) Uani 1 1 d . . . 
C10 C 0.6613(7) 0.4097(9) 0.3205(6) 0.0527(15) Uani 1 1 d . . . 
H10A H 0.5469 0.3931 0.3235 0.063 Uiso 1 1 calc R . . 
H10B H 0.6242 0.5499 0.3058 0.063 Uiso 1 1 calc R . . 
C3 C 1.2823(8) 0.0343(9) -0.0999(7) 0.0486(15) Uani 1 1 d . . . 
H3 H 1.3976 -0.0714 -0.1048 0.058 Uiso 1 1 calc R . . 
C11 C 0.7630(9) 0.2728(11) 0.4724(7) 0.0694(18) Uani 1 1 d . . . 
H11A H 0.7862 0.1353 0.4940 0.104 Uiso 1 1 calc R . . 
H11B H 0.6851 0.3170 0.5498 0.104 Uiso 1 1 calc R . . 
H11C H 0.8810 0.2806 0.4683 0.104 Uiso 1 1 calc R . . 
C9 C 0.9435(7) 0.2161(8) 0.1872(6) 0.0438(13) Uani 1 1 d . . . 
H8 H 1.0039 0.1179 0.2770 0.053 Uiso 1 1 calc R . . 
C2 C 1.2066(7) 0.0424(8) 0.0371(7) 0.0473(14) Uani 1 1 d . . . 
H2 H 1.2707 -0.0581 0.1248 0.057 Uiso 1 1 calc R . . 
C6 C 0.9393(6) 0.3481(7) -0.0856(6) 0.0335(11) Uani 1 1 d . . . 
C1 C 1.0314(6) 0.2030(8) 0.0452(6) 0.0419(14) Uani 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 
Br C4 1.905(5) . ? 
C4 C3 1.361(8) . ? 
C4 C5 1.403(7) . ? 
O2 C8 1.378(7) . ? 
O2 C7 1.391(6) . ? 
O1 C7 1.192(7) . ? 
C7 C6 1.481(7) . ? 
C5 C6 1.406(7) . ? 
C5 H5 0.9300 . ? 
C8 C9 1.326(7) . ? 
C8 C10 1.492(6) . ? 
C10 C11 1.537(10) . ? 
C10 H10A 0.9700 . ? 
C10 H10B 0.9700 . ? 
C3 C2 1.374(8) . ? 
C3 H3 0.9300 . ? 
C11 H11A 0.9600 . ? 
C11 H11B 0.9600 . ? 
C11 H11C 0.9600 . ? 
C9 C1 1.452(7) . ? 
C9 H8 0.9300 . ? 
C2 C1 1.414(6) . ? 
C2 H2 0.9300 . ? 
C6 C1 1.369(7) . ? 
 
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 
C3 C4 C5 122.2(5) . . ? 
C3 C4 Br 120.2(4) . . ? 
C5 C4 Br 117.6(5) . . ? 
C8 O2 C7 123.6(4) . . ? 
O1 C7 O2 118.1(5) . . ? 
O1 C7 C6 127.1(5) . . ? 
O2 C7 C6 114.8(6) . . ? 
C4 C5 C6 116.7(5) . . ? 
C4 C5 H5 121.6 . . ? 
C6 C5 H5 121.6 . . ? 
C9 C8 O2 121.2(5) . . ? 
C9 C8 C10 129.4(6) . . ? 
O2 C8 C10 109.4(4) . . ? 
C8 C10 C11 114.1(5) . . ? 
C8 C10 H10A 108.7 . . ? 
C11 C10 H10A 108.7 . . ? 
C8 C10 H10B 108.7 . . ? 
C11 C10 H10B 108.7 . . ? 
H10A C10 H10B 107.6 . . ? 
C4 C3 C2 120.0(5) . . ? 
C4 C3 H3 120.0 . . ? 
C2 C3 H3 120.0 . . ? 
C10 C11 H11A 109.5 . . ? 
C10 C11 H11B 109.5 . . ? 
H11A C11 H11B 109.5 . . ? 
C10 C11 H11C 109.5 . . ? 
H11A C11 H11C 109.5 . . ? 
H11B C11 H11C 109.5 . . ? 
C8 C9 C1 120.2(5) . . ? 
C8 C9 H8 119.9 . . ? 
C1 C9 H8 119.9 . . ? 
C3 C2 C1 120.2(6) . . ? 
C3 C2 H2 119.9 . . ? 
C1 C2 H2 119.9 . . ? 
C1 C6 C5 122.1(4) . . ? 
C1 C6 C7 121.0(5) . . ? 
C5 C6 C7 116.8(5) . . ? 
C6 C1 C2 118.7(5) . . ? 
C6 C1 C9 119.0(4) . . ? 
C2 C1 C9 122.3(6) . . ? 
 
_diffrn_measured_fraction_theta_max    0.761 
_diffrn_reflns_theta_full              24.99 
_diffrn_measured_fraction_theta_full   'ACTA 50' 
_refine_diff_density_max    0.821 
_refine_diff_density_min   -0.598 
_refine_diff_density_rms    0.094 

#===END



