data_C22H19BrNOP 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C22 H19 Br N O P' 
_chemical_formula_sum 
 'C22 H19 Br N O P' 
_chemical_formula_weight          424.26 
 
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' 
 'Br'  'Br'  -0.2901   2.4595 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting           'Tetragonal'
_symmetry_space_group_name_H-M   'I 4' 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-y, x, z' 
 'y, -x, z' 
 '-x, -y, z' 
 'x+1/2, y+1/2, z+1/2' 
 '-y+1/2, x+1/2, z+1/2' 
 'y+1/2, -x+1/2, z+1/2' 
 '-x+1/2, -y+1/2, z+1/2' 
 
_cell_length_a                    27.1750(9) 
_cell_length_b                    27.1750(9) 
_cell_length_c                    5.2579(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      3882.9(2) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     6852
_cell_measurement_theta_min       2.37
_cell_measurement_theta_max       26.37 
 
_exptl_crystal_description        needle 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.05 
_exptl_crystal_size_min           0.03 
_exptl_crystal_density_meas       'not measured' 
_exptl_crystal_density_diffrn     1.452 
_exptl_crystal_density_method     none 
_exptl_crystal_F_000              1728 
_exptl_absorpt_coefficient_mu     2.210 
_exptl_absorpt_correction_type    'multi-scan' 
_exptl_absorpt_correction_T_min   0.6662 
_exptl_absorpt_correction_T_max   0.9367 
_exptl_absorpt_process_details    
;
Sheldrick, G.M. (2008). SADABS v2008/1. Bruker AXS Inc. Madison, WI USA.
;
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       100(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   'Bruker Kappa DUO CCD diffractometer'
_diffrn_measurement_method        '\f and \w scans'  
_diffrn_detector_area_resol_mean  ?   
_diffrn_reflns_number             29844 
_diffrn_reflns_av_R_equivalents   0.1011 
_diffrn_reflns_av_sigmaI/netI     0.0827 
_diffrn_reflns_limit_h_min        -36 
_diffrn_reflns_limit_h_max        36 
_diffrn_reflns_limit_k_min        -36 
_diffrn_reflns_limit_k_max        34 
_diffrn_reflns_limit_l_min        -7 
_diffrn_reflns_limit_l_max        6 
_diffrn_reflns_theta_min          1.50 
_diffrn_reflns_theta_max          28.34 
_reflns_number_total              4780 
_reflns_number_gt                 3632 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
 
_refine_special_details 
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.0735P)^2^+26.5294P] where P=(Fo^2^+2Fc^2^)/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        na
_chemical_absolute_configuration  ad 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.03(2) 
_refine_ls_number_reflns          4780 
_refine_ls_number_parameters      282 
_refine_ls_number_restraints      287 
_refine_ls_R_factor_all           0.1098 
_refine_ls_R_factor_gt            0.0770 
_refine_ls_wR_factor_ref          0.1901 
_refine_ls_wR_factor_gt           0.1752 
_refine_ls_goodness_of_fit_ref    1.058 
_refine_ls_restrained_S_all       1.060 
_refine_ls_shift/su_max           0.001 
_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 0.70812(4) 1.00894(4) 0.1788(3) 0.0147(3) Uani 1 1 d . B . 
O1 O 0.70714(13) 0.98890(14) -0.0839(8) 0.0197(8) Uani 1 1 d . . . 
N1 N 0.71537(16) 0.96477(16) 0.3927(9) 0.0148(9) Uani 1 1 d D . . 
H1N H 0.716(2) 0.972(2) 0.562(5) 0.018 Uiso 1 1 d D . . 
C1 C 0.65253(18) 1.03930(18) 0.2745(10) 0.0183(10) Uani 1 1 d DU . . 
C4 C 0.5653(3) 1.0861(3) 0.4041(13) 0.0467(18) Uani 1 1 d DU . . 
H4 H 0.5335 1.1004 0.4177 0.056 Uiso 1 1 calc R A 1 
C2 C 0.6173(4) 1.0125(4) 0.413(2) 0.029(3) Uani 0.538(8) 1 d PDU B 1 
H2 H 0.6227 0.9792 0.4597 0.035 Uiso 0.538(8) 1 calc PR B 1 
C3 C 0.5722(4) 1.0379(4) 0.482(3) 0.036(3) Uani 0.538(8) 1 d PDU B 1 
H3 H 0.5477 1.0216 0.5793 0.043 Uiso 0.538(8) 1 calc PR B 1 
C5 C 0.6016(4) 1.1127(4) 0.312(3) 0.0359(19) Uani 0.538(8) 1 d PDU B 1 
H5 H 0.5982 1.1472 0.2911 0.043 Uiso 0.538(8) 1 calc PR B 1 
C6 C 0.6453(4) 1.0889(3) 0.245(2) 0.024(2) Uani 0.538(8) 1 d PDU B 1 
H6 H 0.6713 1.1080 0.1760 0.029 Uiso 0.538(8) 1 calc PR B 1 
C2X C 0.6366(4) 1.0425(5) 0.5204(18) 0.023(3) Uani 0.462(8) 1 d PDU B 2 
H2X H 0.6558 1.0280 0.6512 0.028 Uiso 0.462(8) 1 calc PR B 2 
C3X C 0.5931(5) 1.0663(7) 0.585(2) 0.041(4) Uani 0.462(8) 1 d PDU B 2 
H3X H 0.5833 1.0684 0.7586 0.049 Uiso 0.462(8) 1 calc PR B 2 
C5X C 0.5859(5) 1.0928(5) 0.164(2) 0.0359(19) Uani 0.462(8) 1 d PDU B 2 
H5X H 0.5705 1.1151 0.0499 0.043 Uiso 0.462(8) 1 calc PR B 2 
C6X C 0.6303(4) 1.0668(4) 0.079(2) 0.021(3) Uani 0.462(8) 1 d PDU B 2 
H6X H 0.6428 1.0684 -0.0892 0.026 Uiso 0.462(8) 1 calc PR B 2 
C7 C 0.75644(18) 1.05466(18) 0.2031(13) 0.0213(11) Uani 1 1 d U . . 
C8 C 0.7587(2) 1.0867(2) 0.4014(15) 0.0345(15) Uani 1 1 d U B . 
H8 H 0.7338 1.0860 0.5279 0.041 Uiso 1 1 calc R . . 
C9 C 0.7972(2) 1.1205(2) 0.4222(16) 0.0364(16) Uani 1 1 d U . . 
H9 H 0.7977 1.1435 0.5582 0.044 Uiso 1 1 calc R B . 
C10 C 0.8343(2) 1.1205(2) 0.2460(16) 0.0395(17) Uani 1 1 d U B . 
H10 H 0.8610 1.1428 0.2604 0.047 Uiso 1 1 calc R . . 
C11 C 0.8322(3) 1.0878(3) 0.0498(15) 0.0392(17) Uani 1 1 d U . . 
H11 H 0.8581 1.0874 -0.0714 0.047 Uiso 1 1 calc R B . 
C12 C 0.7934(3) 1.0551(3) 0.0215(15) 0.0373(16) Uani 1 1 d U B . 
H12 H 0.7922 1.0334 -0.1199 0.045 Uiso 1 1 calc R . . 
C13 C 0.7538(2) 0.9273(2) 0.3438(11) 0.0190(11) Uani 1 1 d DU . . 
H13 H 0.754(2) 0.919(2) 0.158(5) 0.023 Uiso 1 1 d D . . 
C14 C 0.8032(2) 0.9474(2) 0.3999(12) 0.0217(12) Uani 1 1 d U C . 
C15 C 0.8417(2) 0.9667(2) 0.4342(15) 0.0331(15) Uani 1 1 d U . . 
C16 C 0.8877(2) 0.9928(3) 0.4727(19) 0.0467(17) Uani 1 1 d U C 1 
H16A H 0.9042 0.9799 0.6268 0.056 Uiso 1 1 calc R C 1 
H16B H 0.8807 1.0281 0.5013 0.056 Uiso 1 1 calc R C 1 
Br1 Br 0.92958(4) 0.98636(5) 0.1969(3) 0.0359(4) Uani 0.498(2) 1 d PU C 1 
Br1X Br 0.92126(5) 0.97798(6) 0.7655(3) 0.0449(5) Uani 0.502(2) 1 d P C 2 
C17 C 0.7433(2) 0.88022(19) 0.4900(12) 0.0202(11) Uani 1 1 d U . . 
C18 C 0.7706(2) 0.8657(2) 0.6948(14) 0.0263(11) Uani 1 1 d U . . 
H18 H 0.7972 0.8856 0.7516 0.032 Uiso 1 1 calc R . . 
C19 C 0.7600(2) 0.8224(2) 0.8196(13) 0.0285(13) Uani 1 1 d U . . 
H19 H 0.7793 0.8132 0.9628 0.034 Uiso 1 1 calc R . . 
C20 C 0.7219(2) 0.7917(2) 0.7419(12) 0.0303(14) Uani 1 1 d U . . 
H20 H 0.7147 0.7618 0.8279 0.036 Uiso 1 1 calc R . . 
C21 C 0.6951(3) 0.8070(3) 0.5327(13) 0.0346(15) Uani 1 1 d U . . 
H21 H 0.6692 0.7866 0.4732 0.042 Uiso 1 1 calc R . . 
C22 C 0.7041(2) 0.8501(2) 0.4079(13) 0.0305(14) Uani 1 1 d U . . 
H22 H 0.6842 0.8597 0.2677 0.037 Uiso 1 1 calc R . . 
 
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 
P1 0.0147(6) 0.0173(6) 0.0122(6) -0.0034(6) -0.0006(6) -0.0003(4) 
O1 0.0202(19) 0.0213(19) 0.017(2) -0.0007(16) 0.0011(16) 0.0010(15) 
N1 0.016(2) 0.016(2) 0.012(2) -0.0004(18) -0.0016(17) 0.0037(17) 
C1 0.014(2) 0.023(2) 0.019(3) -0.007(2) -0.0017(19) 0.0002(18) 
C4 0.038(4) 0.059(4) 0.044(4) -0.023(3) -0.008(3) 0.029(3) 
C2 0.036(6) 0.035(6) 0.016(6) 0.007(5) 0.010(5) 0.010(4) 
C3 0.023(5) 0.065(7) 0.020(6) 0.007(6) 0.005(5) 0.011(5) 
C5 0.031(4) 0.026(4) 0.050(5) -0.002(4) -0.010(4) 0.016(3) 
C6 0.032(5) 0.015(4) 0.026(6) -0.003(4) -0.004(4) 0.003(4) 
C2X 0.027(6) 0.024(6) 0.019(6) -0.002(5) 0.007(5) 0.013(5) 
C3X 0.034(8) 0.065(10) 0.022(6) -0.008(7) 0.005(5) 0.026(7) 
C5X 0.031(4) 0.026(4) 0.050(5) -0.002(4) -0.010(4) 0.016(3) 
C6X 0.033(6) 0.016(6) 0.015(5) 0.003(5) 0.009(5) 0.002(5) 
C7 0.022(2) 0.020(2) 0.022(3) 0.006(2) -0.011(2) -0.0052(19) 
C8 0.027(3) 0.027(3) 0.049(4) -0.013(3) 0.000(3) -0.008(2) 
C9 0.032(3) 0.024(3) 0.053(5) -0.010(3) -0.011(3) -0.009(2) 
C10 0.029(3) 0.030(3) 0.060(5) 0.010(3) -0.015(3) -0.013(2) 
C11 0.028(3) 0.049(4) 0.040(4) 0.004(3) 0.001(3) -0.018(3) 
C12 0.036(4) 0.039(4) 0.037(4) 0.002(3) 0.001(3) -0.015(3) 
C13 0.019(2) 0.021(3) 0.017(3) -0.002(2) 0.002(2) 0.004(2) 
C14 0.022(3) 0.017(2) 0.026(3) 0.000(2) 0.003(2) 0.0092(19) 
C15 0.024(3) 0.031(3) 0.044(4) 0.004(3) 0.000(3) 0.002(2) 
C16 0.026(3) 0.054(4) 0.060(5) 0.009(4) -0.006(3) -0.009(3) 
Br1 0.0236(6) 0.0411(7) 0.0430(9) 0.0116(7) 0.0027(6) -0.0017(5) 
Br1X 0.0381(8) 0.0547(10) 0.0419(9) -0.0084(7) -0.0061(6) 0.0025(6) 
C17 0.022(3) 0.015(2) 0.024(3) -0.006(2) 0.005(2) 0.0042(19) 
C18 0.025(3) 0.026(3) 0.028(3) 0.003(3) 0.005(3) 0.007(2) 
C19 0.028(3) 0.028(3) 0.030(4) 0.003(2) 0.001(2) 0.006(2) 
C20 0.038(3) 0.024(3) 0.029(4) -0.008(2) 0.006(3) 0.005(2) 
C21 0.036(4) 0.032(3) 0.036(4) -0.004(3) -0.004(3) -0.007(3) 
C22 0.029(3) 0.028(3) 0.034(4) -0.003(3) -0.009(3) -0.002(2) 
 
_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 1.485(4) . ? 
P1 N1 1.657(5) . ? 
P1 C1 1.793(5) . ? 
P1 C7 1.812(5) . ? 
N1 C13 1.480(7) . ? 
N1 H1N 0.91(2) . ? 
C1 C2X 1.367(9) . ? 
C1 C6 1.371(8) . ? 
C1 C6X 1.405(8) . ? 
C1 C2 1.407(8) . ? 
C4 C5 1.315(10) . ? 
C4 C3X 1.331(10) . ? 
C4 C3 1.386(10) . ? 
C4 C5X 1.393(10) . ? 
C4 H4 0.9500 . ? 
C2 C3 1.451(13) . ? 
C2 H2 0.9500 . ? 
C3 H3 0.9500 . ? 
C5 C6 1.397(13) . ? 
C5 H5 0.9500 . ? 
C6 H6 0.9500 . ? 
C2X C3X 1.389(14) . ? 
C2X H2X 0.9500 . ? 
C3X H3X 0.9500 . ? 
C5X C6X 1.469(14) . ? 
C5X H5X 0.9500 . ? 
C6X H6X 0.9500 . ? 
C7 C8 1.359(9) . ? 
C7 C12 1.386(9) . ? 
C8 C9 1.398(8) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.368(11) . ? 
C9 H9 0.9500 . ? 
C10 C11 1.362(11) . ? 
C10 H10 0.9500 . ? 
C11 C12 1.386(9) . ? 
C11 H11 0.9500 . ? 
C12 H12 0.9500 . ? 
C13 C14 1.479(8) . ? 
C13 C17 1.520(8) . ? 
C13 H13 1.00(2) . ? 
C14 C15 1.186(9) . ? 
C15 C16 1.451(9) . ? 
C16 Br1 1.851(9) . ? 
C16 H16A 0.9900 . ? 
C16 H16B 0.9900 . ? 
Br1 Br1 2.7566(16) 3_575 ? 
Br1 Br1 2.7567(16) 2_755 ? 
C17 C18 1.366(9) . ? 
C17 C22 1.412(8) . ? 
C18 C19 1.378(8) . ? 
C18 H18 0.9500 . ? 
C19 C20 1.390(9) . ? 
C19 H19 0.9500 . ? 
C20 C21 1.384(10) . ? 
C20 H20 0.9500 . ? 
C21 C22 1.364(9) . ? 
C21 H21 0.9500 . ? 
C22 H22 0.9500 . ? 
 
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 N1 111.6(2) . . ? 
O1 P1 C1 114.5(2) . . ? 
N1 P1 C1 104.1(2) . . ? 
O1 P1 C7 109.3(3) . . ? 
N1 P1 C7 111.3(3) . . ? 
C1 P1 C7 106.0(2) . . ? 
C13 N1 P1 117.6(4) . . ? 
C13 N1 H1N 108(4) . . ? 
P1 N1 H1N 121(4) . . ? 
C2X C1 C6 89.9(8) . . ? 
C2X C1 C6X 121.3(8) . . ? 
C6 C1 C6X 48.2(7) . . ? 
C2X C1 C2 47.7(7) . . ? 
C6 C1 C2 118.0(7) . . ? 
C6X C1 C2 111.2(8) . . ? 
C2X C1 P1 124.2(6) . . ? 
C6 C1 P1 122.8(5) . . ? 
C6X C1 P1 113.7(6) . . ? 
C2 C1 P1 118.7(5) . . ? 
C5 C4 C3X 93.4(11) . . ? 
C5 C4 C3 121.8(8) . . ? 
C3X C4 C3 47.9(9) . . ? 
C5 C4 C5X 45.0(8) . . ? 
C3X C4 C5X 118.4(9) . . ? 
C3 C4 C5X 109.7(9) . . ? 
C5 C4 H4 119.1 . . ? 
C3X C4 H4 128.9 . . ? 
C3 C4 H4 119.1 . . ? 
C5X C4 H4 112.3 . . ? 
C1 C2 C3 117.2(8) . . ? 
C1 C2 H2 121.4 . . ? 
C3 C2 H2 121.4 . . ? 
C4 C3 C2 119.4(9) . . ? 
C4 C3 H3 120.3 . . ? 
C2 C3 H3 120.3 . . ? 
C4 C5 C6 118.4(9) . . ? 
C4 C5 H5 120.8 . . ? 
C6 C5 H5 120.8 . . ? 
C1 C6 C5 123.3(9) . . ? 
C1 C6 H6 118.4 . . ? 
C5 C6 H6 118.4 . . ? 
C1 C2X C3X 122.2(10) . . ? 
C1 C2X H2X 118.9 . . ? 
C3X C2X H2X 118.9 . . ? 
C4 C3X C2X 119.6(11) . . ? 
C4 C3X H3X 120.2 . . ? 
C2X C3X H3X 120.2 . . ? 
C4 C5X C6X 122.8(9) . . ? 
C4 C5X H5X 118.6 . . ? 
C6X C5X H5X 118.6 . . ? 
C1 C6X C5X 112.8(9) . . ? 
C1 C6X H6X 123.6 . . ? 
C5X C6X H6X 123.6 . . ? 
C8 C7 C12 119.3(5) . . ? 
C8 C7 P1 121.8(5) . . ? 
C12 C7 P1 118.9(5) . . ? 
C7 C8 C9 121.1(7) . . ? 
C7 C8 H8 119.5 . . ? 
C9 C8 H8 119.5 . . ? 
C10 C9 C8 119.8(7) . . ? 
C10 C9 H9 120.1 . . ? 
C8 C9 H9 120.1 . . ? 
C11 C10 C9 118.9(6) . . ? 
C11 C10 H10 120.6 . . ? 
C9 C10 H10 120.6 . . ? 
C10 C11 C12 122.0(7) . . ? 
C10 C11 H11 119.0 . . ? 
C12 C11 H11 119.0 . . ? 
C11 C12 C7 118.9(7) . . ? 
C11 C12 H12 120.6 . . ? 
C7 C12 H12 120.6 . . ? 
C14 C13 N1 110.6(4) . . ? 
C14 C13 C17 112.3(5) . . ? 
N1 C13 C17 111.1(4) . . ? 
C14 C13 H13 106(3) . . ? 
N1 C13 H13 109(4) . . ? 
C17 C13 H13 108(4) . . ? 
C15 C14 C13 174.8(6) . . ? 
C14 C15 C16 177.0(7) . . ? 
C15 C16 Br1 111.9(6) . . ? 
C15 C16 H16A 109.2 . . ? 
Br1 C16 H16A 109.2 . . ? 
C15 C16 H16B 109.2 . . ? 
Br1 C16 H16B 109.2 . . ? 
H16A C16 H16B 107.9 . . ? 
C16 Br1 Br1 105.4(3) . 3_575 ? 
C16 Br1 Br1 124.2(3) . 2_755 ? 
Br1 Br1 Br1 89.998(1) 3_575 2_755 ? 
C18 C17 C22 118.9(5) . . ? 
C18 C17 C13 122.8(5) . . ? 
C22 C17 C13 118.3(5) . . ? 
C17 C18 C19 120.6(6) . . ? 
C17 C18 H18 119.7 . . ? 
C19 C18 H18 119.7 . . ? 
C18 C19 C20 121.8(6) . . ? 
C18 C19 H19 119.1 . . ? 
C20 C19 H19 119.1 . . ? 
C21 C20 C19 116.5(6) . . ? 
C21 C20 H20 121.8 . . ? 
C19 C20 H20 121.8 . . ? 
C22 C21 C20 123.1(6) . . ? 
C22 C21 H21 118.4 . . ? 
C20 C21 H21 118.4 . . ? 
C21 C22 C17 119.0(6) . . ? 
C21 C22 H22 120.5 . . ? 
C17 C22 H22 120.5 . . ? 
 
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 
O1 P1 N1 C13 46.0(4) . . . . ? 
C1 P1 N1 C13 170.0(4) . . . . ? 
C7 P1 N1 C13 -76.3(5) . . . . ? 
O1 P1 C1 C2X 152.1(8) . . . . ? 
N1 P1 C1 C2X 30.0(8) . . . . ? 
C7 P1 C1 C2X -87.4(8) . . . . ? 
O1 P1 C1 C6 -92.2(7) . . . . ? 
N1 P1 C1 C6 145.7(7) . . . . ? 
C7 P1 C1 C6 28.3(7) . . . . ? 
O1 P1 C1 C6X -37.9(7) . . . . ? 
N1 P1 C1 C6X -160.0(6) . . . . ? 
C7 P1 C1 C6X 82.6(7) . . . . ? 
O1 P1 C1 C2 95.8(7) . . . . ? 
N1 P1 C1 C2 -26.3(7) . . . . ? 
C7 P1 C1 C2 -143.7(7) . . . . ? 
C2X C1 C2 C3 69.9(12) . . . . ? 
C6 C1 C2 C3 9.1(14) . . . . ? 
C6X C1 C2 C3 -43.8(13) . . . . ? 
P1 C1 C2 C3 -178.5(8) . . . . ? 
C5 C4 C3 C2 -13.0(18) . . . . ? 
C3X C4 C3 C2 -75.3(13) . . . . ? 
C5X C4 C3 C2 35.6(15) . . . . ? 
C1 C2 C3 C4 1.7(17) . . . . ? 
C3X C4 C5 C6 53.8(14) . . . . ? 
C3 C4 C5 C6 12.7(18) . . . . ? 
C5X C4 C5 C6 -74.0(13) . . . . ? 
C2X C1 C6 C5 -50.1(13) . . . . ? 
C6X C1 C6 C5 84.3(13) . . . . ? 
C2 C1 C6 C5 -9.9(15) . . . . ? 
P1 C1 C6 C5 178.0(9) . . . . ? 
C4 C5 C6 C1 -1.0(18) . . . . ? 
C6 C1 C2X C3X 49.4(15) . . . . ? 
C6X C1 C2X C3X 10.9(19) . . . . ? 
C2 C1 C2X C3X -80.2(15) . . . . ? 
P1 C1 C2X C3X -179.8(12) . . . . ? 
C5 C4 C3X C2X -54.6(17) . . . . ? 
C3 C4 C3X C2X 76.5(16) . . . . ? 
C5X C4 C3X C2X -15(2) . . . . ? 
C1 C2X C3X C4 1(2) . . . . ? 
C5 C4 C5X C6X 82.0(15) . . . . ? 
C3X C4 C5X C6X 18.3(19) . . . . ? 
C3 C4 C5X C6X -33.6(16) . . . . ? 
C2X C1 C6X C5X -7.6(15) . . . . ? 
C6 C1 C6X C5X -64.3(11) . . . . ? 
C2 C1 C6X C5X 44.9(13) . . . . ? 
P1 C1 C6X C5X -178.0(9) . . . . ? 
C4 C5X C6X C1 -6.7(18) . . . . ? 
O1 P1 C7 C8 165.0(5) . . . . ? 
N1 P1 C7 C8 -71.3(5) . . . . ? 
C1 P1 C7 C8 41.2(6) . . . . ? 
O1 P1 C7 C12 -18.5(6) . . . . ? 
N1 P1 C7 C12 105.1(5) . . . . ? 
C1 P1 C7 C12 -142.4(5) . . . . ? 
C12 C7 C8 C9 1.2(10) . . . . ? 
P1 C7 C8 C9 177.7(5) . . . . ? 
C7 C8 C9 C10 -2.5(11) . . . . ? 
C8 C9 C10 C11 1.5(11) . . . . ? 
C9 C10 C11 C12 0.8(12) . . . . ? 
C10 C11 C12 C7 -2.1(12) . . . . ? 
C8 C7 C12 C11 1.0(10) . . . . ? 
P1 C7 C12 C11 -175.5(6) . . . . ? 
P1 N1 C13 C14 77.0(5) . . . . ? 
P1 N1 C13 C17 -157.7(4) . . . . ? 
N1 C13 C14 C15 -47(7) . . . . ? 
C17 C13 C14 C15 -172(7) . . . . ? 
C13 C14 C15 C16 19(21) . . . . ? 
C14 C15 C16 Br1 -101(15) . . . . ? 
C15 C16 Br1 Br1 151.8(5) . . . 3_575 ? 
C15 C16 Br1 Br1 -107.4(5) . . . 2_755 ? 
C14 C13 C17 C18 15.8(8) . . . . ? 
N1 C13 C17 C18 -108.6(6) . . . . ? 
C14 C13 C17 C22 -163.4(5) . . . . ? 
N1 C13 C17 C22 72.2(7) . . . . ? 
C22 C17 C18 C19 -0.2(9) . . . . ? 
C13 C17 C18 C19 -179.3(5) . . . . ? 
C17 C18 C19 C20 0.8(9) . . . . ? 
C18 C19 C20 C21 -0.1(9) . . . . ? 
C19 C20 C21 C22 -1.1(10) . . . . ? 
C20 C21 C22 C17 1.7(10) . . . . ? 
C18 C17 C22 C21 -1.0(9) . . . . ? 
C13 C17 C22 C21 178.2(6) . . . . ? 
 
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 O1  0.91(2) 1.93(2) 2.838(6) 171(6) 1_556 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              28.34 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    0.874 
_refine_diff_density_min   -0.686 
_refine_diff_density_rms    0.113