 
data_s92
 
_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C24 H21 Br N2 O4 S'
_chemical_formula_sum
 'C24 H21 Br N2 O4 S'
_chemical_formula_weight          513.40
 
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'
 '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            Monoclinic
_symmetry_space_group_name_H-M    P21/c
_symmetry_space_group_name_hall   '-P 2ybc'
 
loop_
 _symmetry_equiv_pos_as_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    10.4834(4)
_cell_length_b                    16.5076(7)
_cell_length_c                    12.7374(3)
_cell_angle_alpha                 90.00
_cell_angle_beta                  96.520(2)
_cell_angle_gamma                 90.00
_cell_volume                      2190.02(14)
_cell_formula_units_Z             4
_cell_measurement_temperature     120(2)
_cell_measurement_reflns_used     9903
_cell_measurement_theta_min       2.91
_cell_measurement_theta_max       27.48
 
_exptl_crystal_description        Plate
_exptl_crystal_colour             Colourless
_exptl_crystal_size_max           0.25
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.04
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.557
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              1048
_exptl_absorpt_coefficient_mu     2.007
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6338
_exptl_absorpt_correction_T_max   0.9240
_exptl_absorpt_process_details    'SORTAV (Blessing, 1997)'
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       120(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'Enraf Nonius FR591 rotating anode'
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Enraf Nonius KappaCCD area detector'
_diffrn_measurement_method        'ω and φ scans to fill Ewald sphere'
_diffrn_detector_area_resol_mean  '9.091 pixels/mm'
_diffrn_standards_number          'n/a'
_diffrn_standards_interval_count  'n/a'
_diffrn_standards_interval_time   'n/a'
_diffrn_standards_decay_%         'n/a'
_diffrn_reflns_number             7239
_diffrn_reflns_av_R_equivalents   0.0335
_diffrn_reflns_av_sigmaI/netI     0.0537
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -19
_diffrn_reflns_limit_k_max        19
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.94
_diffrn_reflns_theta_max          25.03
_reflns_number_total              3872
_reflns_number_gt                 2719
_reflns_threshold_expression      >2σ(I)
 
_computing_data_collection        
;
'DENZO (Otwinowski and Minor, 1997) & COLLECT (Hooft, 1998) '
;
_computing_cell_refinement        'DENZO and COLLECT'
_computing_data_reduction         'DENZO and COLLECT'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 2008)' 
_computing_molecular_graphics     'PLATON (Watkin, Pearce 1995)'
_computing_publication_material   SHELXL-97
 
_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)+(0.0627P)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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          3872
_refine_ls_number_parameters      253
_refine_ls_number_restraints      8
_refine_ls_R_factor_all           0.0714
_refine_ls_R_factor_gt            0.0424
_refine_ls_wR_factor_ref          0.1143
_refine_ls_wR_factor_gt           0.1026
_refine_ls_goodness_of_fit_ref    1.013
_refine_ls_restrained_S_all       2.436
_refine_ls_shift/su_max           0.010
_refine_ls_shift/su_mean          0.001
 
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 0.1447(8) -0.3083(6) 0.6301(6) 0.040(2) Uani 1 1 d . . .
H1A H 0.1967 -0.2594 0.6448 0.060 Uiso 1 1 calc R . .
H1B H 0.0797 -0.2983 0.5700 0.060 Uiso 1 1 calc R . .
H1C H 0.2001 -0.3531 0.6133 0.060 Uiso 1 1 calc R . .
C2 C -0.1140(8) -0.3912(5) 0.9553(7) 0.042(2) Uani 1 1 d . . .
H2A H -0.0859 -0.4431 0.9874 0.062 Uiso 1 1 calc R . .
H2B H -0.2047 -0.3949 0.9267 0.062 Uiso 1 1 calc R . .
H2C H -0.1033 -0.3484 1.0089 0.062 Uiso 1 1 calc R . .
C3 C 0.3580(7) -0.3498(4) 0.9269(5) 0.0236(16) Uani 1 1 d . . .
C4 C 0.2913(7) -0.3327(4) 0.8272(5) 0.0234(16) Uani 1 1 d . . .
H4 H 0.3361 -0.3152 0.7705 0.028 Uiso 1 1 calc R . .
C5 C 0.1604(7) -0.3419(4) 0.8132(5) 0.0248(17) Uani 1 1 d . . .
C6 C 0.0904(7) -0.3671(4) 0.8973(6) 0.0276(17) Uani 1 1 d . . .
C7 C 0.1564(7) -0.3847(5) 0.9947(6) 0.0283(18) Uani 1 1 d . . .
H7 H 0.1124 -0.4018 1.0520 0.034 Uiso 1 1 calc R . .
C8 C 0.2894(7) -0.3766(5) 1.0061(5) 0.0262(17) Uani 1 1 d . . .
C9 C 0.5009(7) -0.3455(5) 0.9561(5) 0.0267(17) Uani 1 1 d . A .
H9 H 0.5434 -0.3802 0.9059 0.032 Uiso 1 1 calc R . .
C10 C 0.5590(7) -0.2600(5) 0.9555(5) 0.0288(18) Uani 1 1 d . . .
H10A H 0.6532 -0.2648 0.9561 0.035 Uiso 1 1 calc R . .
H10B H 0.5250 -0.2324 0.8892 0.035 Uiso 1 1 calc R . .
C11 C 0.5306(8) -0.2079(5) 1.0488(6) 0.0321(19) Uani 1 1 d . A .
C12 C 0.4456(8) -0.1370(5) 1.0316(5) 0.0304(19) Uani 1 1 d . . .
C13 C 0.3610(8) -0.1285(5) 0.9389(6) 0.034(2) Uani 1 1 d . . .
H13 H 0.3562 -0.1702 0.8873 0.041 Uiso 1 1 calc R . .
C14 C 0.2838(8) -0.0602(5) 0.9209(6) 0.036(2) Uani 1 1 d . . .
H14 H 0.2280 -0.0545 0.8572 0.043 Uiso 1 1 calc R . .
C15 C 0.2901(9) -0.0011(5) 0.9973(7) 0.041(2) Uani 1 1 d . . .
C16 C 0.3732(8) -0.0067(5) 1.0901(6) 0.040(2) Uani 1 1 d . . .
H16 H 0.3772 0.0355 1.1412 0.048 Uiso 1 1 calc R . .
C17 C 0.4500(8) -0.0744(5) 1.1069(6) 0.036(2) Uani 1 1 d . . .
H17 H 0.5066 -0.0789 1.1704 0.044 Uiso 1 1 calc R . .
C18A C 0.6381(10) -0.3698(10) 1.1295(12) 0.0356(13) Uani 0.582(10) 1 d PG A 1
C19A C 0.7158(11) -0.4367(8) 1.1559(11) 0.0356(13) Uani 0.582(10) 1 d PG A 1
H19A H 0.6893 -0.4890 1.1311 0.043 Uiso 0.582(10) 1 calc PR A 1
C20A C 0.8323(9) -0.4269(6) 1.2185(8) 0.0356(13) Uani 0.582(10) 1 d PGD A 1
H20A H 0.8854 -0.4726 1.2366 0.043 Uiso 0.582(10) 1 calc PR A 1
C21A C 0.8710(7) -0.3504(5) 1.2547(6) 0.0356(13) Uani 0.582(10) 1 d PGD A 1
C22A C 0.7933(10) -0.2836(6) 1.2283(9) 0.0356(13) Uani 0.582(10) 1 d PGD A 1
H22A H 0.8198 -0.2313 1.2531 0.043 Uiso 0.582(10) 1 calc PR A 1
C23A C 0.6768(11) -0.2933(9) 1.1657(12) 0.0356(13) Uani 0.582(10) 1 d PG A 1
C24A C 0.9939(8) -0.3401(7) 1.3208(8) 0.0356(13) Uani 0.582(10) 1 d PD A 1
H24A H 1.0360 -0.3929 1.3320 0.053 Uiso 0.582(10) 1 calc PR A 1
H24B H 0.9786 -0.3170 1.3891 0.053 Uiso 0.582(10) 1 calc PR A 1
H24C H 1.0491 -0.3036 1.2854 0.053 Uiso 0.582(10) 1 calc PR A 1
C18B C 0.6412(14) -0.3614(13) 1.1315(17) 0.0356(13) Uani 0.418(10) 1 d PG A 2
C19B C 0.7309(14) -0.4204(10) 1.1659(14) 0.0356(13) Uani 0.418(10) 1 d PGD A 2
H19B H 0.7171 -0.4751 1.1443 0.043 Uiso 0.418(10) 1 calc PR A 2
C20B C 0.8406(10) -0.3994(8) 1.2320(9) 0.0356(13) Uani 0.418(10) 1 d PGD A 2
C21B C 0.8607(12) -0.3194(8) 1.2636(10) 0.0356(13) Uani 0.418(10) 1 d PGD A 2
H21B H 0.9358 -0.3051 1.3087 0.043 Uiso 0.418(10) 1 calc PR A 2
C22B C 0.7711(17) -0.2604(9) 1.2292(14) 0.0356(13) Uani 0.418(10) 1 d PG A 2
H22B H 0.7848 -0.2057 1.2508 0.043 Uiso 0.418(10) 1 calc PR A 2
C23B C 0.6613(16) -0.2814(12) 1.1631(17) 0.0356(13) Uani 0.418(10) 1 d PG A 2
C24B C 0.9351(14) -0.4617(8) 1.2682(12) 0.0356(13) Uani 0.418(10) 1 d PD A 2
H24D H 0.9050 -0.5146 1.2408 0.053 Uiso 0.418(10) 1 calc PR A 2
H24E H 0.9462 -0.4632 1.3456 0.053 Uiso 0.418(10) 1 calc PR A 2
H24F H 1.0175 -0.4489 1.2425 0.053 Uiso 0.418(10) 1 calc PR A 2
N1 N 0.5218(6) -0.3825(4) 1.0626(4) 0.0273(15) Uani 1 1 d . . .
N2 N 0.5844(7) -0.2213(4) 1.1435(5) 0.0374(17) Uani 1 1 d . . .
O1 O 0.0831(5) -0.3286(3) 0.7208(4) 0.0341(13) Uani 1 1 d . . .
O2 O -0.0386(5) -0.3726(4) 0.8721(4) 0.0384(14) Uani 1 1 d . . .
O3 O 0.3780(5) -0.3428(3) 1.2034(4) 0.0361(14) Uani 1 1 d . . .
O4 O 0.3830(5) -0.4836(3) 1.1484(4) 0.0394(14) Uani 1 1 d . . .
S1 S 0.39162(19) -0.39973(12) 1.11958(14) 0.0283(5) Uani 1 1 d . A .
Br1 Br 0.18365(10) 0.09173(6) 0.97091(8) 0.0545(4) Uani 1 1 d . . .
 
 
_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
C1 O1 1.426(9) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O2 1.426(9) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C8 1.377(10) . ?
C3 C4 1.408(9) . ?
C3 C9 1.503(10) . ?
C4 C5 1.372(10) . ?
C4 H4 0.9500 . ?
C5 O1 1.369(8) . ?
C5 C6 1.427(10) . ?
C6 O2 1.357(9) . ?
C6 C7 1.381(10) . ?
C7 C8 1.392(10) . ?
C7 H7 0.9500 . ?
C8 S1 1.741(8) . ?
C9 N1 1.481(9) . ?
C9 C10 1.537(11) . ?
C9 H9 1.0000 . ?
C10 C11 1.523(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N2 1.291(10) . ?
C11 C12 1.473(12) . ?
C12 C13 1.401(11) . ?
C12 C17 1.407(11) . ?
C13 C14 1.391(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.374(11) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(13) . ?
C15 Br1 1.902(9) . ?
C16 C17 1.380(12) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18A C19A 1.3900 . ?
C18A C23A 1.3900 . ?
C18A N1 1.422(9) . ?
C19A C20A 1.3900 . ?
C19A H19A 0.9500 . ?
C20A C21A 1.3900 . ?
C20A H20A 0.9500 . ?
C21A C22A 1.3900 . ?
C21A C24A 1.4656(16) . ?
C22A C23A 1.3900 . ?
C22A H22A 0.9500 . ?
C23A N2 1.539(12) . ?
C24A H24A 0.9800 . ?
C24A H24B 0.9800 . ?
C24A H24C 0.9800 . ?
C18B C19B 1.3900 . ?
C18B C23B 1.3900 . ?
C18B N1 1.487(12) . ?
C19B C20B 1.3900 . ?
C19B H19B 0.9500 . ?
C20B C21B 1.3900 . ?
C20B C24B 1.4653(16) . ?
C21B C22B 1.3900 . ?
C21B H21B 0.9500 . ?
C22B C23B 1.3900 . ?
C22B H22B 0.9500 . ?
C23B N2 1.284(15) . ?
C24B H24D 0.9800 . ?
C24B H24E 0.9800 . ?
C24B H24F 0.9800 . ?
N1 S1 1.641(6) . ?
O3 S1 1.441(5) . ?
O4 S1 1.438(6) . ?
 
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 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C8 C3 C4 118.6(7) . . ?
C8 C3 C9 115.0(6) . . ?
C4 C3 C9 126.4(6) . . ?
C5 C4 C3 118.8(6) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
O1 C5 C4 125.4(6) . . ?
O1 C5 C6 112.8(6) . . ?
C4 C5 C6 121.8(6) . . ?
O2 C6 C7 125.6(6) . . ?
O2 C6 C5 115.2(6) . . ?
C7 C6 C5 119.2(7) . . ?
C6 C7 C8 117.9(7) . . ?
C6 C7 H7 121.1 . . ?
C8 C7 H7 121.1 . . ?
C3 C8 C7 123.7(7) . . ?
C3 C8 S1 110.8(6) . . ?
C7 C8 S1 125.5(5) . . ?
N1 C9 C3 104.2(5) . . ?
N1 C9 C10 111.5(6) . . ?
C3 C9 C10 115.3(6) . . ?
N1 C9 H9 108.5 . . ?
C3 C9 H9 108.5 . . ?
C10 C9 H9 108.5 . . ?
C11 C10 C9 113.7(6) . . ?
C11 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
C11 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N2 C11 C12 117.9(7) . . ?
N2 C11 C10 121.9(8) . . ?
C12 C11 C10 120.1(7) . . ?
C13 C12 C17 118.0(8) . . ?
C13 C12 C11 121.3(7) . . ?
C17 C12 C11 120.7(7) . . ?
C14 C13 C12 121.4(7) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C15 C14 C13 118.6(8) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C14 C15 C16 122.0(8) . . ?
C14 C15 Br1 117.8(7) . . ?
C16 C15 Br1 120.2(6) . . ?
C17 C16 C15 118.9(8) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C12 121.1(8) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?
C19A C18A C23A 120.0 . . ?
C19A C18A N1 117.9(9) . . ?
C23A C18A N1 122.1(9) . . ?
C20A C19A C18A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C19A C20A C21A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C21A C20A H20A 120.0 . . ?
C22A C21A C20A 120.0 . . ?
C22A C21A C24A 119.99(14) . . ?
C20A C21A C24A 120.01(14) . . ?
C21A C22A C23A 120.0 . . ?
C21A C22A H22A 120.0 . . ?
C23A C22A H22A 120.0 . . ?
C22A C23A C18A 120.0 . . ?
C22A C23A N2 120.7(8) . . ?
C18A C23A N2 119.1(8) . . ?
C21A C24A H24A 109.5 . . ?
C21A C24A H24B 109.5 . . ?
H24A C24A H24B 109.5 . . ?
C21A C24A H24C 109.5 . . ?
H24A C24A H24C 109.5 . . ?
H24B C24A H24C 109.5 . . ?
C19B C18B C23B 120.0 . . ?
C19B C18B N1 121.0(12) . . ?
C23B C18B N1 119.0(12) . . ?
C18B C19B C20B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C20B C19B H19B 120.0 . . ?
C19B C20B C21B 120.0 . . ?
C19B C20B C24B 119.98(14) . . ?
C21B C20B C24B 120.02(14) . . ?
C22B C21B C20B 120.0 . . ?
C22B C21B H21B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C21B C22B C23B 120.0 . . ?
C21B C22B H22B 120.0 . . ?
C23B C22B H22B 120.0 . . ?
N2 C23B C22B 112.6(13) . . ?
N2 C23B C18B 127.3(13) . . ?
C22B C23B C18B 120.0 . . ?
C20B C24B H24D 109.5 . . ?
C20B C24B H24E 109.5 . . ?
H24D C24B H24E 109.5 . . ?
C20B C24B H24F 109.5 . . ?
H24D C24B H24F 109.5 . . ?
H24E C24B H24F 109.5 . . ?
C18A N1 C9 121.0(9) . . ?
C9 N1 C18B 118.1(11) . . ?
C18A N1 S1 117.4(8) . . ?
C9 N1 S1 115.6(5) . . ?
C18B N1 S1 117.8(11) . . ?
C23B N2 C11 120.8(12) . . ?
C11 N2 C23A 120.2(8) . . ?
C5 O1 C1 117.1(6) . . ?
C6 O2 C2 117.4(6) . . ?
O4 S1 O3 115.1(3) . . ?
O4 S1 N1 111.0(3) . . ?
O3 S1 N1 111.8(3) . . ?
O4 S1 C8 111.8(4) . . ?
O3 S1 C8 111.7(3) . . ?
N1 S1 C8 93.4(3) . . ?
 
_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              25.03
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.404
_refine_diff_density_min   -0.545
_refine_diff_density_rms    0.071
