 
data_2013ncs0121 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C19 H25 Br N2 S' 
_chemical_formula_weight          393.38 
 
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' 
 'Br'  'Br'  -0.2901   2.4595 
 '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' 
 'S'  'S'   0.1246   0.1234 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting            ? 
_symmetry_space_group_name_H-M    ? 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 'x+1/2, -y+1/2, -z' 
 '-x, y+1/2, -z+1/2' 
 
_cell_length_a                    12.0601(8) 
_cell_length_b                    12.5854(3) 
_cell_length_c                    12.9527(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1965.98(15) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     ? 
_cell_measurement_theta_min       ? 
_cell_measurement_theta_max       ? 
 
_exptl_crystal_description        ? 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.329 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              816 
_exptl_absorpt_coefficient_mu     2.198 
_exptl_absorpt_correction_type    ? 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
_exptl_absorpt_process_details    ? 
 
_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   ? 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             15819 
_diffrn_reflns_av_R_equivalents   0.0333 
_diffrn_reflns_av_sigmaI/netI     0.0442 
_diffrn_reflns_limit_h_min        -15 
_diffrn_reflns_limit_h_max        15 
_diffrn_reflns_limit_k_min        -16 
_diffrn_reflns_limit_k_max        16 
_diffrn_reflns_limit_l_min        -16 
_diffrn_reflns_limit_l_max        16 
_diffrn_reflns_theta_min          3.15 
_diffrn_reflns_theta_max          27.48 
_reflns_number_total              4486 
_reflns_number_gt                 3978 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_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)+(0.0132P)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     mixed 
_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    -0.006(5) 
_refine_ls_number_reflns          4486 
_refine_ls_number_parameters      211 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0306 
_refine_ls_R_factor_gt            0.0228 
_refine_ls_wR_factor_ref          0.0428 
_refine_ls_wR_factor_gt           0.0407 
_refine_ls_goodness_of_fit_ref    1.022 
_refine_ls_restrained_S_all       1.022 
_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 
Br1 Br -0.623843(14) -0.430681(14) -0.027047(13) 0.02270(5) Uani 1 1 d . . . 
S1 S -0.52615(4) -0.74691(4) -0.24283(4) 0.02502(11) Uani 1 1 d . . . 
N1 N -0.61201(11) -0.79769(11) -0.42674(10) 0.0182(3) Uani 1 1 d . . . 
H1 H -0.5492 -0.8326 -0.4335 0.022 Uiso 1 1 calc R . . 
C18 C -0.83604(15) -1.06040(16) -0.39927(14) 0.0281(4) Uani 1 1 d . . . 
H18 H -0.8151 -1.1269 -0.3707 0.034 Uiso 1 1 calc R . . 
N0AA N -0.70162(11) -0.66322(12) -0.33639(11) 0.0205(3) Uani 1 1 d . . . 
H0AA H -0.7372 -0.6448 -0.3930 0.025 Uiso 1 1 calc R . . 
C16 C -0.97709(14) -0.93794(16) -0.45052(14) 0.0276(4) Uani 1 1 d . . . 
H16 H -1.0533 -0.9205 -0.4582 0.033 Uiso 1 1 calc R . . 
C3 C -0.62295(14) -0.73600(13) -0.34474(12) 0.0181(4) Uani 1 1 d . . . 
C8 C -0.85830(14) -0.74894(15) -0.00525(15) 0.0308(5) Uani 1 1 d . . . 
H8 H -0.8492 -0.7485 0.0676 0.037 Uiso 1 1 calc R . . 
C15 C -0.89679(12) -0.86595(13) -0.48122(14) 0.0216(4) Uani 1 1 d . . . 
H15 H -0.9181 -0.7992 -0.5090 0.026 Uiso 1 1 calc R . . 
C14 C -0.78443(12) -0.89118(12) -0.47145(14) 0.0164(3) Uani 1 1 d . . . 
C10 C -0.52116(15) -0.89059(15) -0.22271(15) 0.0273(4) Uani 1 1 d . . . 
H10A H -0.4999 -0.9255 -0.2882 0.033 Uiso 1 1 calc R . . 
H10B H -0.4633 -0.9070 -0.1709 0.033 Uiso 1 1 calc R . . 
C11 C -0.63108(16) -0.93611(16) -0.18620(14) 0.0366(5) Uani 1 1 d . . . 
H11A H -0.6882 -0.9227 -0.2384 0.055 Uiso 1 1 calc R . . 
H11B H -0.6525 -0.9021 -0.1211 0.055 Uiso 1 1 calc R . . 
H11C H -0.6234 -1.0128 -0.1755 0.055 Uiso 1 1 calc R . . 
C17 C -0.94766(15) -1.03475(16) -0.40891(15) 0.0290(5) Uani 1 1 d . . . 
H17 H -1.0031 -1.0834 -0.3871 0.035 Uiso 1 1 calc R . . 
C9 C -0.79106(14) -0.68538(14) -0.06574(14) 0.0227(4) Uani 1 1 d . . . 
H9 H -0.7360 -0.6421 -0.0344 0.027 Uiso 1 1 calc R . . 
C4 C -0.80394(13) -0.68466(14) -0.17255(14) 0.0198(4) Uani 1 1 d . . . 
C13 C -0.64069(15) -0.84915(16) -0.60723(13) 0.0285(5) Uani 1 1 d . . . 
H13A H -0.5876 -0.7949 -0.6297 0.043 Uiso 1 1 calc R . . 
H13B H -0.6966 -0.8598 -0.6611 0.043 Uiso 1 1 calc R . . 
H13C H -0.6015 -0.9161 -0.5946 0.043 Uiso 1 1 calc R . . 
C5 C -0.88433(14) -0.75008(13) -0.21609(14) 0.0283(4) Uani 1 1 d . . . 
H5 H -0.8937 -0.7509 -0.2889 0.034 Uiso 1 1 calc R . . 
C12 C -0.69709(13) -0.81298(14) -0.50837(13) 0.0185(4) Uani 1 1 d . . . 
H12 H -0.7339 -0.7431 -0.5217 0.022 Uiso 1 1 calc R . . 
C19 C -0.75541(15) -0.98955(15) -0.43106(14) 0.0222(4) Uani 1 1 d . . . 
H19 H -0.6794 -1.0083 -0.4252 0.027 Uiso 1 1 calc R . . 
C2 C -0.79580(14) -0.50775(14) -0.26309(14) 0.0265(4) Uani 1 1 d . . . 
H2A H -0.7494 -0.4631 -0.3075 0.040 Uiso 1 1 calc R . . 
H2B H -0.8123 -0.4697 -0.1989 0.040 Uiso 1 1 calc R . . 
H2C H -0.8652 -0.5245 -0.2989 0.040 Uiso 1 1 calc R . . 
C6 C -0.73446(14) -0.61010(14) -0.23824(13) 0.0199(4) Uani 1 1 d . . . 
H6 H -0.6656 -0.5918 -0.1990 0.024 Uiso 1 1 calc R . . 
C7 C -0.93861(15) -0.81310(15) -0.04916(18) 0.0360(6) Uani 1 1 d . . . 
H7 H -0.9848 -0.8561 -0.0069 0.043 Uiso 1 1 calc R . . 
C1A C -0.95071(16) -0.81386(17) -0.15504(18) 0.0358(5) Uani 1 1 d . . . 
H1A H -1.0049 -0.8584 -0.1861 0.043 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 
S1 C3 1.7675(16) . ? 
S1 C10 1.8280(19) . ? 
N1 C3 1.322(2) . ? 
N1 C12 1.486(2) . ? 
C18 C19 1.382(3) . ? 
C18 C17 1.390(3) . ? 
N0AA C3 1.323(2) . ? 
N0AA C6 1.490(2) . ? 
C16 C17 1.379(3) . ? 
C16 C15 1.385(2) . ? 
C8 C9 1.382(2) . ? 
C8 C7 1.383(3) . ? 
C15 C14 1.398(2) . ? 
C14 C19 1.389(2) . ? 
C14 C12 1.519(2) . ? 
C10 C11 1.520(3) . ? 
C9 C4 1.392(2) . ? 
C4 C5 1.391(2) . ? 
C4 C6 1.519(2) . ? 
C13 C12 1.520(2) . ? 
C5 C1A 1.382(3) . ? 
C2 C6 1.520(2) . ? 
C7 C1A 1.379(3) . ? 
 
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 S1 C10 101.83(8) . . ? 
C3 N1 C12 125.36(14) . . ? 
C19 C18 C17 120.32(19) . . ? 
C3 N0AA C6 124.82(14) . . ? 
C17 C16 C15 120.70(17) . . ? 
N1 C3 N0AA 122.94(15) . . ? 
N1 C3 S1 119.23(13) . . ? 
N0AA C3 S1 117.79(12) . . ? 
C9 C8 C7 121.03(19) . . ? 
C16 C15 C14 120.23(17) . . ? 
C19 C14 C15 118.75(16) . . ? 
C19 C14 C12 121.43(14) . . ? 
C15 C14 C12 119.77(15) . . ? 
C11 C10 S1 112.87(14) . . ? 
C16 C17 C18 119.32(18) . . ? 
C8 C9 C4 120.10(18) . . ? 
C5 C4 C9 118.47(17) . . ? 
C5 C4 C6 121.53(17) . . ? 
C9 C4 C6 119.95(16) . . ? 
C1A C5 C4 121.02(19) . . ? 
N1 C12 C14 109.79(14) . . ? 
N1 C12 C13 109.22(12) . . ? 
C14 C12 C13 112.43(14) . . ? 
C18 C19 C14 120.66(17) . . ? 
N0AA C6 C4 110.33(14) . . ? 
N0AA C6 C2 109.20(14) . . ? 
C4 C6 C2 111.95(14) . . ? 
C1A C7 C8 119.14(19) . . ? 
C7 C1A C5 120.23(19) . . ? 
 
_diffrn_measured_fraction_theta_max    0.998 
_diffrn_reflns_theta_full              27.48 
_diffrn_measured_fraction_theta_full   0.998 
_refine_diff_density_max    0.324 
_refine_diff_density_min   -0.215 
_refine_diff_density_rms    0.055 
