data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C21 H24 Br N O'
_chemical_formula_weight          386.32
 
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            Monoclinic
_symmetry_space_group_name_H-M    Cc
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 'x, -y, z+1/2'
 'x+1/2, y+1/2, z'
 'x+1/2, -y+1/2, z+1/2'
 
_cell_length_a                    14.845(3)
_cell_length_b                    15.000(3)
_cell_length_c                    9.0450(18)
_cell_angle_alpha                 90.00
_cell_angle_beta                  115.04(3)
_cell_angle_gamma                 90.00
_cell_volume                      1824.8(6)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     13383
_cell_measurement_theta_min       1.00
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        plate
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.24
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.05
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.406
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              800
_exptl_absorpt_coefficient_mu     2.260
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6131
_exptl_absorpt_correction_T_max   0.8954
_exptl_absorpt_process_details    SORTAV
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius KappaCCD Area Detector'
_diffrn_measurement_method        'Phi and Omega scans to fill Ewald Sphere'
_diffrn_detector_area_resol_mean  9.091
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             7242
_diffrn_reflns_av_R_equivalents   0.0642
_diffrn_reflns_av_sigmaI/netI     0.0766
_diffrn_reflns_limit_h_min        -16
_diffrn_reflns_limit_h_max        19
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        19
_diffrn_reflns_limit_l_min        -11
_diffrn_reflns_limit_l_max        11
_diffrn_reflns_theta_min          2.03
_diffrn_reflns_theta_max          27.44
_reflns_number_total              3768
_reflns_number_gt                 3225
_reflns_threshold_expression      >2sigma(I)
 
_computing_data_collection        ?
_computing_cell_refinement        'DENZO, COLLECT'
_computing_data_reduction         'DENZO, COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'CAMERON (Watkin, Pearce 1995)'
_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)+(0.0497P)²+2.2969P] 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      SHELXL
_refine_ls_extinction_coef        0.0048(9)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details
 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    -0.010(12)
_refine_ls_number_reflns          3768
_refine_ls_number_parameters      220
_refine_ls_number_restraints      2
_refine_ls_R_factor_all           0.0613
_refine_ls_R_factor_gt            0.0481
_refine_ls_wR_factor_ref          0.1159
_refine_ls_wR_factor_gt           0.1076
_refine_ls_goodness_of_fit_ref    1.024
_refine_ls_restrained_S_all       1.024
_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
C1 C 0.7873(3) 0.6619(3) 0.3330(5) 0.0306(9) Uani 1 1 d . . .
C2 C 0.8602(3) 0.6250(3) 0.2961(5) 0.0330(10) Uani 1 1 d . . .
H2 H 0.9282 0.6352 0.3663 0.040 Uiso 1 1 calc R . .
C3 C 0.8352(3) 0.5730(3) 0.1569(5) 0.0353(10) Uani 1 1 d . . .
C4 C 0.7356(4) 0.5467(3) 0.0758(6) 0.0382(11) Uani 1 1 d . . .
H4 H 0.7175 0.4997 -0.0019 0.046 Uiso 1 1 calc R . .
C5 C 0.6638(3) 0.5893(3) 0.1092(6) 0.0367(10) Uani 1 1 d . . .
H5 H 0.5961 0.5728 0.0498 0.044 Uiso 1 1 calc R . .
C6 C 0.6874(3) 0.6557(3) 0.2271(5) 0.0313(9) Uani 1 1 d . . .
C7 C 0.6134(3) 0.7295(3) 0.2093(6) 0.0355(10) Uani 1 1 d . . .
H7A H 0.6115 0.7399 0.3161 0.043 Uiso 1 1 calc R . .
H7B H 0.5463 0.7104 0.1311 0.043 Uiso 1 1 calc R . .
C8 C 0.6410(3) 0.8194(3) 0.1477(5) 0.0336(10) Uani 1 1 d . . .
H8A H 0.5794 0.8536 0.0854 0.040 Uiso 1 1 calc R . .
H8B H 0.6837 0.8557 0.2431 0.040 Uiso 1 1 calc R . .
C9 C 0.6948(3) 0.8033(3) 0.0406(5) 0.0300(9) Uani 1 1 d . . .
C10 C 0.6530(4) 0.7484(3) -0.0969(6) 0.0379(11) Uani 1 1 d . . .
H10 H 0.5827 0.7437 -0.1523 0.045 Uiso 1 1 calc R . .
C11 C 0.7114(4) 0.7011(3) -0.1538(5) 0.0391(10) Uani 1 1 d . . .
H11 H 0.6809 0.6663 -0.2501 0.047 Uiso 1 1 calc R . .
C12 C 0.8147(4) 0.7037(3) -0.0716(6) 0.0369(10) Uani 1 1 d . . .
C13 C 0.8546(3) 0.7723(3) 0.0397(6) 0.0300(10) Uani 1 1 d . . .
H13 H 0.9236 0.7850 0.0793 0.036 Uiso 1 1 calc R . .
C14 C 0.7971(3) 0.8233(3) 0.0955(5) 0.0280(9) Uani 1 1 d . . .
C15 C 0.8772(4) 0.6260(4) -0.0763(6) 0.0460(13) Uani 1 1 d . . .
H15A H 0.9386 0.6484 -0.0813 0.055 Uiso 1 1 calc R . .
H15B H 0.8401 0.5906 -0.1762 0.055 Uiso 1 1 calc R . .
C16 C 0.9061(4) 0.5638(3) 0.0787(6) 0.0425(11) Uani 1 1 d . . .
H16A H 0.9068 0.5010 0.0458 0.051 Uiso 1 1 calc R . .
H16B H 0.9740 0.5791 0.1597 0.051 Uiso 1 1 calc R . .
C17 C 0.8523(3) 0.8904(3) 0.2250(5) 0.0295(9) Uani 1 1 d . . .
C18 C 0.7473(3) 1.0139(3) 0.0511(5) 0.0326(9) Uani 1 1 d . . .
H18A H 0.7230 0.9659 -0.0319 0.039 Uiso 1 1 calc R . .
H18B H 0.7797 1.0596 0.0111 0.039 Uiso 1 1 calc R . .
C19 C 0.6590(4) 1.0557(4) 0.0676(7) 0.0505(13) Uani 1 1 d . . .
H19A H 0.6252 1.0105 0.1041 0.076 Uiso 1 1 calc R . .
H19B H 0.6127 1.0796 -0.0382 0.076 Uiso 1 1 calc R . .
H19C H 0.6822 1.1042 0.1478 0.076 Uiso 1 1 calc R . .
C20 C 0.8838(4) 1.0413(3) 0.3252(6) 0.0387(11) Uani 1 1 d . . .
H20A H 0.9073 1.0149 0.4356 0.046 Uiso 1 1 calc R . .
H20B H 0.8433 1.0944 0.3215 0.046 Uiso 1 1 calc R . .
C21 C 0.9723(4) 1.0696(4) 0.2958(6) 0.0445(12) Uani 1 1 d . . .
H21A H 1.0125 1.0172 0.2993 0.067 Uiso 1 1 calc R . .
H21B H 1.0125 1.1120 0.3804 0.067 Uiso 1 1 calc R . .
H21C H 0.9493 1.0981 0.1884 0.067 Uiso 1 1 calc R . .
N1 N 0.8216(3) 0.9763(2) 0.2042(4) 0.0290(8) Uani 1 1 d . . .
O1 O 0.9280(2) 0.8672(2) 0.3458(4) 0.0391(8) Uani 1 1 d . . .
Br1 Br 0.82537(4) 0.73130(3) 0.52692(4) 0.04194(18) 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
C1 C2 1.377(6) . ?
C1 C6 1.386(6) . ?
C1 Br1 1.908(4) . ?
C2 C3 1.391(6) . ?
C3 C4 1.401(7) . ?
C3 C16 1.502(7) . ?
C4 C5 1.383(7) . ?
C5 C6 1.391(7) . ?
C6 C7 1.520(7) . ?
C7 C8 1.577(7) . ?
C8 C9 1.514(6) . ?
C9 C10 1.398(7) . ?
C9 C14 1.416(6) . ?
C10 C11 1.378(8) . ?
C11 C12 1.394(7) . ?
C12 C13 1.385(7) . ?
C12 C15 1.502(7) . ?
C13 C14 1.389(6) . ?
C14 C17 1.498(6) . ?
C15 C16 1.584(7) . ?
C17 O1 1.240(5) . ?
C17 N1 1.353(6) . ?
C18 N1 1.470(5) . ?
C18 C19 1.517(7) . ?
C20 N1 1.465(6) . ?
C20 C21 1.508(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
C2 C1 C6 121.8(4) . . ?
C2 C1 Br1 119.0(3) . . ?
C6 C1 Br1 119.1(3) . . ?
C1 C2 C3 120.6(4) . . ?
C2 C3 C4 116.7(4) . . ?
C2 C3 C16 120.4(4) . . ?
C4 C3 C16 121.5(4) . . ?
C5 C4 C3 119.7(4) . . ?
C4 C5 C6 122.1(4) . . ?
C1 C6 C5 115.3(4) . . ?
C1 C6 C7 122.6(4) . . ?
C5 C6 C7 120.2(4) . . ?
C6 C7 C8 112.1(4) . . ?
C9 C8 C7 112.1(4) . . ?
C10 C9 C14 116.3(4) . . ?
C10 C9 C8 120.5(4) . . ?
C14 C9 C8 121.4(4) . . ?
C11 C10 C9 121.6(5) . . ?
C10 C11 C12 120.7(4) . . ?
C13 C12 C11 116.4(4) . . ?
C13 C12 C15 121.2(4) . . ?
C11 C12 C15 121.1(5) . . ?
C12 C13 C14 122.2(4) . . ?
C13 C14 C9 119.3(4) . . ?
C13 C14 C17 115.9(4) . . ?
C9 C14 C17 124.5(4) . . ?
C12 C15 C16 111.8(4) . . ?
C3 C16 C15 112.4(4) . . ?
O1 C17 N1 121.0(4) . . ?
O1 C17 C14 119.5(4) . . ?
N1 C17 C14 119.4(4) . . ?
N1 C18 C19 113.6(4) . . ?
N1 C20 C21 112.1(4) . . ?
C17 N1 C20 117.5(4) . . ?
C17 N1 C18 124.8(4) . . ?
C20 N1 C18 115.7(4) . . ?
 
_diffrn_measured_fraction_theta_max    0.986
_diffrn_reflns_theta_full              27.44
_diffrn_measured_fraction_theta_full   0.986
_refine_diff_density_max    0.742
_refine_diff_density_min   -0.616
_refine_diff_density_rms    0.070
