 
data_s92 
 
_audit_creation_method            SHELXL 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_structural      ? 
_chemical_formula_analytical      ? 
_chemical_formula_sum             'C26 H26 Br N O' 
_chemical_formula_weight          448.39 
_chemical_melting_point           ? 
_chemical_compound_source         ? 
 
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            Orthorhombic 
_symmetry_space_group_name_H-M    P2(1)2(1)2(1) 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 
_cell_length_a                    8.028(3) 
_cell_length_b                    10.396(2) 
_cell_length_c                    24.955(2) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      2082.7(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       2.12 
_cell_measurement_theta_max       25.03 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.08 
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.05 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.430 
_exptl_crystal_density_method     ? 
_exptl_crystal_F_000              928 
_exptl_absorpt_coefficient_mu     1.991 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71069 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device        ? 
_diffrn_measurement_method        ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             8160 
_diffrn_reflns_av_R_equivalents   0.0790 
_diffrn_reflns_av_sigmaI/netI     0.2683 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -8 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -27 
_diffrn_reflns_limit_l_max        26 
_diffrn_reflns_theta_min          2.12 
_diffrn_reflns_theta_max          25.03 
_reflns_number_total              3192 
_reflns_number_observed           1229 
_reflns_observed_criterion        >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-86 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-92 (Sheldrick, 1993)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_refine_special_details 
; 
 Refinement on F² for ALL reflections except for 0 with very negative F² 
 or flagged by the user for potential systematic errors.  Weighted R-factors 
 wR and all goodnesses of fit S are based on F², conventional R-factors R 
 are based on F, with F set to zero for negative F². The observed criterion 
 of F² > 2sigma(F²) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     ? 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    0.277(13) 
_refine_ls_number_reflns          3192 
_refine_ls_number_parameters      264 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1004 
_refine_ls_R_factor_obs           0.0327 
_refine_ls_wR_factor_all          0.0584 
_refine_ls_wR_factor_obs          0.0468 
_refine_ls_goodness_of_fit_all    0.470 
_refine_ls_goodness_of_fit_obs    0.654 
_refine_ls_restrained_S_all       0.470 
_refine_ls_restrained_S_obs       0.654 
_refine_ls_shift/esd_max          -0.026 
_refine_ls_shift/esd_mean         0.003 
 
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_thermal_displace_type 
 _atom_site_occupancy 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_group 
Br1 Br 0.48437(7) 0.74871(9) 0.15878(3) 0.0539(2) Uani 1 d . . 
O1 O 0.5555(4) 1.0484(4) 0.2153(2) 0.0408(13) Uani 1 d . . 
N1 N 0.6815(5) 1.0357(5) 0.1342(2) 0.0269(14) Uani 1 d . . 
C1 C 0.7660(7) 0.9640(6) 0.0935(3) 0.029(2) Uani 1 d . . 
C2 C 0.9206(7) 0.9052(6) 0.1028(3) 0.031(2) Uani 1 d . . 
C3 C 0.9774(7) 0.8230(5) 0.0628(3) 0.034(2) Uani 1 d . . 
H3 H 1.0623(7) 0.7651(5) 0.0705(3) 0.041 Uiso 1 calc R . 
C4 C 0.9107(7) 0.8256(6) 0.0125(3) 0.040(2) Uani 1 d . . 
H4 H 0.9504(7) 0.7682(6) -0.0130(3) 0.048 Uiso 1 calc R . 
C5 C 0.7841(7) 0.9121(6) -0.0018(3) 0.032(2) Uani 1 d . . 
C6 C 0.7041(7) 0.9692(6) 0.0412(3) 0.029(2) Uani 1 d . . 
H6 H 0.6049(7) 1.0128(6) 0.0351(3) 0.035 Uiso 1 calc R . 
C7 C 1.0344(6) 0.9466(5) 0.1476(3) 0.040(2) Uani 1 d . . 
H7A H 1.0819(6) 0.8708(5) 0.1643(3) 0.048 Uiso 1 calc R . 
H7B H 0.9695(6) 0.9916(5) 0.1745(3) 0.048 Uiso 1 calc R . 
C8 C 1.1808(7) 1.0373(7) 0.1281(3) 0.049(2) Uani 1 d . . 
H8A H 1.1888(7) 1.1102(7) 0.1522(3) 0.059 Uiso 1 calc R . 
H8B H 1.2849(7) 0.9902(7) 0.1301(3) 0.059 Uiso 1 calc R . 
C9 C 1.1578(7) 1.0863(6) 0.0717(3) 0.038(2) Uani 1 d . . 
C10 C 1.0370(6) 1.1774(5) 0.0604(2) 0.030(2) Uani 1 d . . 
H10 H 1.0018(6) 1.2336(5) 0.0871(2) 0.036 Uiso 1 calc R . 
C11 C 0.9695(7) 1.1850(5) 0.0106(3) 0.033(2) Uani 1 d . . 
H11 H 0.8911(7) 1.2485(5) 0.0033(3) 0.040 Uiso 1 calc R . 
C12 C 1.0153(8) 1.0996(5) -0.0299(2) 0.033(2) Uani 1 d . . 
C13 C 1.1576(8) 1.0276(6) -0.0229(3) 0.043(2) Uani 1 d . . 
H13 H 1.2063(8) 0.9844(6) -0.0516(3) 0.052 Uiso 1 calc R . 
C14 C 1.2269(7) 1.0212(6) 0.0283(3) 0.043(2) Uani 1 d . . 
H14 H 1.3222(7) 0.9720(6) 0.0337(3) 0.052 Uiso 1 calc R . 
C15 C 0.8956(7) 1.0676(6) -0.0747(3) 0.044(2) Uani 1 d . . 
H15A H 0.9582(7) 1.0387(6) -0.1057(3) 0.053 Uiso 1 calc R . 
H15B H 0.8351(7) 1.1446(6) -0.0848(3) 0.053 Uiso 1 calc R . 
C16 C 0.7661(7) 0.9586(6) -0.0578(3) 0.041(2) Uani 1 d . . 
H16A H 0.6542(7) 0.9918(6) -0.0625(3) 0.050 Uiso 1 calc R . 
H16B H 0.7791(7) 0.8860(6) -0.0819(3) 0.050 Uiso 1 calc R . 
C17 C 0.6141(6) 1.1633(5) 0.1207(2) 0.032(2) Uani 1 d . . 
H17A H 0.5149(20) 1.1534(5) 0.0996(9) 0.048 Uiso 1 calc R . 
H17B H 0.6955(15) 1.2109(11) 0.1006(10) 0.048 Uiso 1 calc R . 
H17C H 0.5880(31) 1.2090(11) 0.1531(2) 0.048 Uiso 1 calc R . 
C18 C 0.6324(7) 0.9860(6) 0.1827(3) 0.029(2) Uani 1 d . . 
C19 C 0.6641(7) 0.8442(6) 0.1936(2) 0.032(2) Uani 1 d . . 
H19 H 0.7701(7) 0.8198(6) 0.1770(2) 0.039 Uiso 1 calc R . 
C20 C 0.6726(6) 0.8146(5) 0.2527(2) 0.037(2) Uani 1 d . . 
H20A H 0.5819(6) 0.8580(5) 0.2709(2) 0.045 Uiso 1 calc R . 
H20B H 0.6587(6) 0.7227(5) 0.2580(2) 0.045 Uiso 1 calc R . 
C21 C 0.8364(8) 0.8567(8) 0.2769(3) 0.037(2) Uani 1 d . . 
C22 C 0.9762(9) 0.7816(6) 0.2696(2) 0.051(2) Uani 1 d . . 
H22 H 0.9678(9) 0.7027(6) 0.2524(2) 0.061 Uiso 1 calc R . 
C23 C 1.1283(8) 0.8239(8) 0.2880(3) 0.058(3) Uani 1 d . . 
H23 H 1.2226(8) 0.7738(8) 0.2824(3) 0.069 Uiso 1 calc R . 
C24 C 1.1426(9) 0.9386(8) 0.3144(3) 0.054(3) Uani 1 d . . 
H24 H 1.2464(9) 0.9669(8) 0.3260(3) 0.065 Uiso 1 calc R . 
C25 C 1.0050(9) 1.0110(6) 0.3237(2) 0.044(2) Uani 1 d . . 
H25 H 1.0141(9) 1.0867(6) 0.3433(2) 0.053 Uiso 1 calc R . 
C26 C 0.8520(8) 0.9734(7) 0.3044(3) 0.039(2) Uani 1 d . . 
H26 H 0.7592(8) 1.0255(7) 0.3096(3) 0.047 Uiso 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 
Br1 C19 1.955(5) . ? 
O1 C18 1.212(6) . ? 
N1 C18 1.373(7) . ? 
N1 C1 1.431(7) . ? 
N1 C17 1.472(6) . ? 
C1 C6 1.396(8) . ? 
C1 C2 1.403(7) . ? 
C2 C3 1.390(7) . ? 
C2 C7 1.507(8) . ? 
C3 C4 1.365(8) . ? 
C4 C5 1.403(7) . ? 
C5 C6 1.385(8) . ? 
C5 C16 1.485(9) . ? 
C7 C8 1.583(7) . ? 
C8 C9 1.509(8) . ? 
C9 C10 1.384(7) . ? 
C9 C14 1.391(8) . ? 
C10 C11 1.359(7) . ? 
C11 C12 1.394(7) . ? 
C12 C13 1.377(8) . ? 
C12 C15 1.513(7) . ? 
C13 C14 1.396(9) . ? 
C15 C16 1.595(7) . ? 
C18 C19 1.520(7) . ? 
C19 C20 1.508(7) . ? 
C20 C21 1.512(8) . ? 
C21 C22 1.379(7) . ? 
C21 C26 1.400(9) . ? 
C22 C23 1.376(8) . ? 
C23 C24 1.367(10) . ? 
C24 C25 1.357(8) . ? 
C25 C26 1.376(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 
C18 N1 C1 124.4(5) . . ? 
C18 N1 C17 115.8(5) . . ? 
C1 N1 C17 118.8(5) . . ? 
C6 C1 C2 119.0(6) . . ? 
C6 C1 N1 118.3(5) . . ? 
C2 C1 N1 121.9(6) . . ? 
C3 C2 C1 116.1(6) . . ? 
C3 C2 C7 120.6(6) . . ? 
C1 C2 C7 122.3(6) . . ? 
C4 C3 C2 121.2(6) . . ? 
C3 C4 C5 122.1(6) . . ? 
C6 C5 C4 114.3(7) . . ? 
C6 C5 C16 123.0(6) . . ? 
C4 C5 C16 121.3(7) . . ? 
C5 C6 C1 122.9(6) . . ? 
C2 C7 C8 113.1(5) . . ? 
C9 C8 C7 113.4(5) . . ? 
C10 C9 C14 117.0(7) . . ? 
C10 C9 C8 120.4(7) . . ? 
C14 C9 C8 120.8(6) . . ? 
C11 C10 C9 120.3(6) . . ? 
C10 C11 C12 121.4(6) . . ? 
C13 C12 C11 118.3(6) . . ? 
C13 C12 C15 120.0(6) . . ? 
C11 C12 C15 120.5(6) . . ? 
C12 C13 C14 118.1(7) . . ? 
C9 C14 C13 122.0(7) . . ? 
C12 C15 C16 112.0(5) . . ? 
C5 C16 C15 114.7(5) . . ? 
O1 C18 N1 122.5(6) . . ? 
O1 C18 C19 119.0(6) . . ? 
N1 C18 C19 118.4(6) . . ? 
C20 C19 C18 112.4(5) . . ? 
C20 C19 Br1 111.3(4) . . ? 
C18 C19 Br1 106.8(4) . . ? 
C21 C20 C19 111.8(5) . . ? 
C22 C21 C26 118.8(6) . . ? 
C22 C21 C20 119.5(7) . . ? 
C26 C21 C20 121.6(6) . . ? 
C23 C22 C21 119.8(6) . . ? 
C24 C23 C22 120.9(7) . . ? 
C23 C24 C25 119.9(7) . . ? 
C24 C25 C26 120.6(6) . . ? 
C25 C26 C21 119.8(6) . . ? 
 
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 
 C18 N1 C1 C6 130.0(6) . . . . ? 
 C17 N1 C1 C6 -38.1(8) . . . . ? 
 C18 N1 C1 C2 -59.6(8) . . . . ? 
 C17 N1 C1 C2 132.3(5) . . . . ? 
 C6 C1 C2 C3 -18.9(8) . . . . ? 
 N1 C1 C2 C3 170.7(5) . . . . ? 
 C6 C1 C2 C7 149.8(6) . . . . ? 
 N1 C1 C2 C7 -20.6(9) . . . . ? 
 C1 C2 C3 C4 16.7(8) . . . . ? 
 C7 C2 C3 C4 -152.2(6) . . . . ? 
 C2 C3 C4 C5 1.0(9) . . . . ? 
 C3 C4 C5 C6 -15.9(8) . . . . ? 
 C3 C4 C5 C16 151.1(6) . . . . ? 
 C4 C5 C6 C1 13.4(9) . . . . ? 
 C16 C5 C6 C1 -153.4(6) . . . . ? 
 C2 C1 C6 C5 3.8(9) . . . . ? 
 N1 C1 C6 C5 174.6(5) . . . . ? 
 C3 C2 C7 C8 68.0(7) . . . . ? 
 C1 C2 C7 C8 -100.2(7) . . . . ? 
 C2 C7 C8 C9 11.9(8) . . . . ? 
 C7 C8 C9 C10 71.5(8) . . . . ? 
 C7 C8 C9 C14 -93.0(7) . . . . ? 
 C14 C9 C10 C11 11.4(8) . . . . ? 
 C8 C9 C10 C11 -153.6(6) . . . . ? 
 C9 C10 C11 C12 2.1(8) . . . . ? 
 C10 C11 C12 C13 -15.5(8) . . . . ? 
 C10 C11 C12 C15 152.7(5) . . . . ? 
 C11 C12 C13 C14 14.5(9) . . . . ? 
 C15 C12 C13 C14 -153.8(6) . . . . ? 
 C10 C9 C14 C13 -12.1(10) . . . . ? 
 C8 C9 C14 C13 152.8(6) . . . . ? 
 C12 C13 C14 C9 -0.9(10) . . . . ? 
 C13 C12 C15 C16 85.3(7) . . . . ? 
 C11 C12 C15 C16 -82.7(7) . . . . ? 
 C6 C5 C16 C15 88.2(7) . . . . ? 
 C4 C5 C16 C15 -77.7(7) . . . . ? 
 C12 C15 C16 C5 1.4(8) . . . . ? 
 C1 N1 C18 O1 -177.1(6) . . . . ? 
 C17 N1 C18 O1 -8.7(8) . . . . ? 
 C1 N1 C18 C19 -2.1(8) . . . . ? 
 C17 N1 C18 C19 166.3(5) . . . . ? 
 O1 C18 C19 C20 -28.6(8) . . . . ? 
 N1 C18 C19 C20 156.2(5) . . . . ? 
 O1 C18 C19 Br1 93.8(6) . . . . ? 
 N1 C18 C19 Br1 -81.4(5) . . . . ? 
 C18 C19 C20 C21 -76.2(7) . . . . ? 
 Br1 C19 C20 C21 164.0(4) . . . . ? 
 C19 C20 C21 C22 -78.7(8) . . . . ? 
 C19 C20 C21 C26 98.1(8) . . . . ? 
 C26 C21 C22 C23 -1.8(10) . . . . ? 
 C20 C21 C22 C23 175.1(7) . . . . ? 
 C21 C22 C23 C24 1.3(12) . . . . ? 
 C22 C23 C24 C25 1.3(13) . . . . ? 
 C23 C24 C25 C26 -3.4(11) . . . . ? 
 C24 C25 C26 C21 2.8(10) . . . . ? 
 C22 C21 C26 C25 -0.3(11) . . . . ? 
 C20 C21 C26 C25 -177.0(5) . . . . ? 
 
_refine_diff_density_max    0.259 
_refine_diff_density_min   -0.254 
_refine_diff_density_rms    0.049 
