 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C14 H22 Br N O3 S' 
_chemical_formula_sum
 'C14 H22 Br N O3 S'
_chemical_formula_weight          364.30
_chemical_absolute_configuration  unknown
 
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'
 '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'
 '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    P21212
_symmetry_space_group_name_hall   P22ab
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, -y, z'
 '-x+1/2, y+1/2, -z'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    14.7756(8)
_cell_length_b                    14.178(3)
_cell_length_c                    7.7793(11)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1629.7(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used    ? 
_cell_measurement_theta_min       ?
_cell_measurement_theta_max      ?

_exptl_crystal_description fragment
_exptl_crystal_colour   colourless
_exptl_crystal_size_max           0.30
_exptl_crystal_size_mid           0.16
_exptl_crystal_size_min           0.14
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.485
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              752
_exptl_absorpt_coefficient_mu     2.657
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source         'rotating anode generator'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Delft instruments FAST area detector'
_diffrn_measurement_method
 'Intensity measurements as described by Darr, Drake, Hursthouse & Malik (1993)'
_diffrn_standards_number         'None'
_diffrn_standards_interval_count 'N/A'
_diffrn_standards_interval_time  'N/A'
_diffrn_standards_decay_%        'N/A'
_diffrn_reflns_number             6530
_diffrn_reflns_av_R_equivalents   0.0495
_diffrn_reflns_av_sigmaI/netI     0.1668
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -9
_diffrn_reflns_limit_l_max        7
_diffrn_reflns_theta_min          2.96
_diffrn_reflns_theta_max          25.03
_reflns_number_total              2841
_reflns_number_gt                 1778
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        'MADNES (Pflugrath & Messerschmidt, 1989)'
_computing_cell_refinement        REFINE
_computing_data_reduction         'ABSURD (Karaulov, 1992)'
_computing_structure_solution     'SIR92 (Altomare, Cascarano, Giacovazzo & Guaglitardi, 1993)'
_computing_structure_refinement   'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material   SHELXL97
 
_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 > 2σ(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)+(0.0000P)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      SHELXL
_refine_ls_extinction_coef        0.016(2)
_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    -0.008(16)
_refine_ls_number_reflns          2841
_refine_ls_number_parameters      207
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0621
_refine_ls_R_factor_gt            0.0453
_refine_ls_wR_factor_ref          0.1268
_refine_ls_wR_factor_gt           0.1065
_refine_ls_goodness_of_fit_ref    0.577
_refine_ls_restrained_S_all       0.577
_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
Br Br 0.16145(6) 0.88439(7) 0.07088(12) 0.0986(4) Uani 1 1 d . . .
S S 0.35441(9) 0.93279(8) 0.44866(16) 0.0403(3) Uani 1 1 d . . .
N N 0.3727(3) 0.8678(2) 0.2709(4) 0.0346(9) Uani 1 1 d . . .
O1 O 0.3864(4) 0.8653(3) -0.0161(5) 0.0818(16) Uani 1 1 d . . .
O2 O 0.3898(3) 1.0248(2) 0.4221(5) 0.0584(10) Uani 1 1 d . . .
O3 O 0.2616(3) 0.9263(3) 0.4965(5) 0.0598(11) Uani 1 1 d . . .
C1 C 0.2756(5) 1.0287(4) -0.0613(9) 0.0682(17) Uani 1 1 d . . .
H1A H 0.2194 1.0664 -0.0698 0.08(2) Uiso 1 1 calc R . .
H1B H 0.2813 0.9907 -0.1675 0.09(2) Uiso 1 1 calc R . .
C2 C 0.2694(4) 0.9638(4) 0.0914(6) 0.0456(13) Uani 1 1 d . . .
H2 H 0.2645 1.0026 0.1984 0.058(15) Uiso 1 1 calc R . .
C3 C 0.3470(4) 0.8963(3) 0.1100(6) 0.0443(12) Uani 1 1 d . . .
C4 C 0.4271(4) 0.8651(3) 0.5832(6) 0.0445(12) Uani 1 1 d . . .
H4A H 0.4815 0.9022 0.6137 0.068(18) Uiso 1 1 calc R . .
H4B H 0.3953 0.8477 0.6906 0.08(2) Uiso 1 1 calc R . .
C5 C 0.4540(3) 0.7774(3) 0.4852(6) 0.0335(10) Uani 1 1 d . . .
C6 C 0.5499(4) 0.7401(3) 0.5123(7) 0.0509(14) Uani 1 1 d . . .
H6A H 0.5637 0.7325 0.6361 0.033(12) Uiso 1 1 calc R . .
H6B H 0.5954 0.7826 0.4599 0.033(12) Uiso 1 1 calc R . .
C7 C 0.5472(4) 0.6434(4) 0.4191(8) 0.0620(16) Uani 1 1 d . . .
H7A H 0.5640 0.5914 0.4980 0.054(16) Uiso 1 1 calc R . .
H7B H 0.5885 0.6427 0.3188 0.12(3) Uiso 1 1 calc R . .
C8 C 0.4468(4) 0.6351(3) 0.3619(7) 0.0560(15) Uani 1 1 d . . .
H8 H 0.4259 0.5690 0.3410 0.08(2) Uiso 1 1 calc R . .
C9 C 0.4335(5) 0.7021(3) 0.2083(7) 0.0581(17) Uani 1 1 d . . .
H9A H 0.4791 0.6905 0.1175 0.066(18) Uiso 1 1 calc R . .
H9B H 0.3721 0.6956 0.1584 0.049(15) Uiso 1 1 calc R . .
C10 C 0.4466(3) 0.7994(3) 0.2916(6) 0.0381(11) Uani 1 1 d . . .
H10 H 0.5046 0.8279 0.2503 0.034(12) Uiso 1 1 calc R . .
C11 C 0.3958(4) 0.6867(3) 0.5058(7) 0.0461(14) Uani 1 1 d . . .
C12 C 0.4071(5) 0.6402(5) 0.6838(8) 0.073(2) Uani 1 1 d . . .
H12A H 0.3760 0.6782 0.7707 0.10(3) Uiso 1 1 calc R . .
H12B H 0.4716 0.6361 0.7122 0.054(16) Uiso 1 1 calc R . .
H12C H 0.3809 0.5767 0.6815 0.054(16) Uiso 1 1 calc R . .
C13 C 0.2937(4) 0.6967(4) 0.4756(11) 0.076(2) Uani 1 1 d . . .
H13A H 0.2658 0.7270 0.5756 0.16(5) Uiso 1 1 calc R . .
H13B H 0.2670 0.6341 0.4587 0.080(19) Uiso 1 1 calc R . .
H13C H 0.2832 0.7354 0.3731 0.060(17) Uiso 1 1 calc R . .
C14 C 0.3564(7) 1.0944(7) -0.0459(14) 0.117(3) Uani 1 1 d . . .
H14A H 0.3665 1.1261 -0.1562 0.18(4) Uiso 1 1 calc R . .
H14B H 0.4102 1.0579 -0.0149 0.13(4) Uiso 1 1 calc R . .
H14C H 0.3444 1.1417 0.0431 0.09(3) Uiso 1 1 calc R . .
 
 
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.959(5) . ?
S O2 1.421(4) . ?
S O3 1.424(4) . ?
S N 1.684(4) . ?
S C4 1.780(5) . ?
N C3 1.369(6) . ?
N C10 1.469(6) . ?
O1 C3 1.223(6) . ?
C1 C2 1.505(7) . ?
C1 C14 1.518(11) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.500(7) . ?
C2 H2 1.0000 . ?
C4 C5 1.512(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.528(7) . ?
C5 C10 1.542(6) . ?
C5 C11 1.556(6) . ?
C6 C7 1.553(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.554(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C11 1.535(8) . ?
C8 C9 1.539(7) . ?
C8 H8 1.0000 . ?
C9 C10 1.537(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 1.0000 . ?
C11 C13 1.532(8) . ?
C11 C12 1.543(7) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
 
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
O2 S O3 116.9(2) . . ?
O2 S N 108.9(2) . . ?
O3 S N 109.5(2) . . ?
O2 S C4 111.0(2) . . ?
O3 S C4 113.1(3) . . ?
N S C4 95.2(2) . . ?
C3 N C10 120.1(4) . . ?
C3 N S 123.0(3) . . ?
C10 N S 113.0(3) . . ?
C2 C1 C14 111.2(6) . . ?
C2 C1 H1A 109.4 . . ?
C14 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
C14 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C1 114.8(5) . . ?
C3 C2 Br 105.3(3) . . ?
C1 C2 Br 109.7(4) . . ?
C3 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
Br C2 H2 109.0 . . ?
O1 C3 N 119.7(5) . . ?
O1 C3 C2 121.1(4) . . ?
N C3 C2 119.2(4) . . ?
C5 C4 S 107.8(3) . . ?
C5 C4 H4A 110.2 . . ?
S C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
S C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C4 C5 C6 117.3(4) . . ?
C4 C5 C10 107.9(4) . . ?
C6 C5 C10 105.7(4) . . ?
C4 C5 C11 118.9(4) . . ?
C6 C5 C11 102.3(4) . . ?
C10 C5 C11 103.2(4) . . ?
C5 C6 C7 102.6(4) . . ?
C5 C6 H6A 111.3 . . ?
C7 C6 H6A 111.3 . . ?
C5 C6 H6B 111.3 . . ?
C7 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
C6 C7 C8 103.0(4) . . ?
C6 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
C6 C7 H7B 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
C11 C8 C9 102.1(4) . . ?
C11 C8 C7 103.0(4) . . ?
C9 C8 C7 107.4(5) . . ?
C11 C8 H8 114.4 . . ?
C9 C8 H8 114.4 . . ?
C7 C8 H8 114.4 . . ?
C10 C9 C8 102.1(4) . . ?
C10 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
C10 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
N C10 C9 116.9(4) . . ?
N C10 C5 107.0(4) . . ?
C9 C10 C5 103.8(4) . . ?
N C10 H10 109.6 . . ?
C9 C10 H10 109.6 . . ?
C5 C10 H10 109.6 . . ?
C13 C11 C8 114.6(5) . . ?
C13 C11 C12 106.5(5) . . ?
C8 C11 C12 113.4(5) . . ?
C13 C11 C5 116.8(4) . . ?
C8 C11 C5 92.7(4) . . ?
C12 C11 C5 112.7(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C14 H14A 109.5 . . ?
C1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
 
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
O2 S N C3 -52.9(5) . . . . ?
O3 S N C3 76.1(4) . . . . ?
C4 S N C3 -167.2(4) . . . . ?
O2 S N C10 104.7(3) . . . . ?
O3 S N C10 -126.4(3) . . . . ?
C4 S N C10 -9.6(4) . . . . ?
C14 C1 C2 C3 -64.3(8) . . . . ?
C14 C1 C2 Br 177.5(6) . . . . ?
C10 N C3 O1 -0.6(8) . . . . ?
S N C3 O1 155.4(5) . . . . ?
C10 N C3 C2 178.1(4) . . . . ?
S N C3 C2 -25.9(6) . . . . ?
C1 C2 C3 O1 -32.1(8) . . . . ?
Br C2 C3 O1 88.6(6) . . . . ?
C1 C2 C3 N 149.2(5) . . . . ?
Br C2 C3 N -90.1(5) . . . . ?
O2 S C4 C5 -122.4(3) . . . . ?
O3 S C4 C5 104.0(4) . . . . ?
N S C4 C5 -9.8(4) . . . . ?
S C4 C5 C6 144.3(4) . . . . ?
S C4 C5 C10 25.2(5) . . . . ?
S C4 C5 C11 -91.7(5) . . . . ?
C4 C5 C6 C7 170.8(4) . . . . ?
C10 C5 C6 C7 -68.9(5) . . . . ?
C11 C5 C6 C7 38.8(5) . . . . ?
C5 C6 C7 C8 -4.0(6) . . . . ?
C6 C7 C8 C11 -32.7(6) . . . . ?
C6 C7 C8 C9 74.6(5) . . . . ?
C11 C8 C9 C10 41.4(6) . . . . ?
C7 C8 C9 C10 -66.5(5) . . . . ?
C3 N C10 C9 -60.3(6) . . . . ?
S N C10 C9 141.4(4) . . . . ?
C3 N C10 C5 -176.2(4) . . . . ?
S N C10 C5 25.5(5) . . . . ?
C8 C9 C10 N -124.4(5) . . . . ?
C8 C9 C10 C5 -6.8(6) . . . . ?
C4 C5 C10 N -31.8(5) . . . . ?
C6 C5 C10 N -158.1(4) . . . . ?
C11 C5 C10 N 94.8(4) . . . . ?
C4 C5 C10 C9 -156.1(4) . . . . ?
C6 C5 C10 C9 77.6(5) . . . . ?
C11 C5 C10 C9 -29.4(5) . . . . ?
C9 C8 C11 C13 64.0(6) . . . . ?
C7 C8 C11 C13 175.3(4) . . . . ?
C9 C8 C11 C12 -173.4(5) . . . . ?
C7 C8 C11 C12 -62.1(6) . . . . ?
C9 C8 C11 C5 -57.2(5) . . . . ?
C7 C8 C11 C5 54.1(4) . . . . ?
C4 C5 C11 C13 52.5(7) . . . . ?
C6 C5 C11 C13 -176.5(5) . . . . ?
C10 C5 C11 C13 -66.9(6) . . . . ?
C4 C5 C11 C8 171.9(4) . . . . ?
C6 C5 C11 C8 -57.1(4) . . . . ?
C10 C5 C11 C8 52.5(4) . . . . ?
C4 C5 C11 C12 -71.3(6) . . . . ?
C6 C5 C11 C12 59.7(5) . . . . ?
C10 C5 C11 C12 169.3(5) . . . . ?
 
_diffrn_measured_fraction_theta_max    0.986
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.986
_refine_diff_density_max    0.558
_refine_diff_density_min   -0.594
_refine_diff_density_rms    0.064
