 
data_SB-B-NCL_0ma_a
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C28 H21 Cl N4 O2 S' 
_chemical_formula_weight          513.00

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'
 'Cl'  'Cl'   0.1484   0.1585
 '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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    13.267(2)
_cell_length_b                    11.8390(19)
_cell_length_c                    16.549(3)
_cell_angle_alpha                 90
_cell_angle_beta                  110.301(5)
_cell_angle_gamma                 90
_cell_volume                      2437.9(7)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     9915
_cell_measurement_theta_min       2.16
_cell_measurement_theta_max       23.42
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.398          
_exptl_crystal_F_000              1064
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           ?
_exptl_crystal_size_mid           ?
_exptl_crystal_size_min           ?
_exptl_absorpt_coefficient_mu     0.277
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             83278
_diffrn_reflns_av_unetI/netI      0.0304
_diffrn_reflns_av_R_equivalents   0.0925
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          1.637
_diffrn_reflns_theta_max          24.999
_diffrn_reflns_theta_full         24.999
_diffrn_measured_fraction_theta_max   1.000
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    1.000
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   1.000
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              4294
_reflns_number_gt                 3362
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²+0.8067P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4294
_refine_ls_number_parameters      325
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0688
_refine_ls_R_factor_gt            0.0501
_refine_ls_wR_factor_ref          0.1747
_refine_ls_wR_factor_gt           0.1473
_refine_ls_goodness_of_fit_ref    1.162
_refine_ls_restrained_S_all       1.162
_refine_ls_shift/su_max           0.000
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.79956(6) 0.12799(6) 0.62902(4) 0.0405(2) Uani 1 1 d . . . . .
Cl1 Cl 0.80735(9) 0.56321(8) 0.84199(6) 0.0733(3) Uani 1 1 d . . . . .
O2 O 0.72155(19) 0.05106(17) 0.63915(14) 0.0565(6) Uani 1 1 d . . . . .
O1 O 0.90512(17) 0.08996(19) 0.63929(13) 0.0566(6) Uani 1 1 d . . . . .
N4 N 0.74778(17) 0.17800(18) 0.53013(13) 0.0346(5) Uani 1 1 d . . . . .
N1 N 0.79699(18) 0.54846(19) 0.42076(14) 0.0385(5) Uani 1 1 d . . . . .
N2 N 0.7734(2) 0.5872(2) 0.55050(15) 0.0442(6) Uani 1 1 d . . . . .
N3 N 0.7655(2) 0.7334(2) 0.44888(17) 0.0555(7) Uani 1 1 d . . . . .
C13 C 0.6665(2) 0.3633(2) 0.49980(17) 0.0351(6) Uani 1 1 d . . . . .
H13 H 0.6826 0.3983 0.5566 0.042 Uiso 1 1 calc R U . . .
C23 C 0.8081(2) 0.2440(2) 0.69767(15) 0.0361(6) Uani 1 1 d . . . . .
C6 C 0.82069(19) 0.4333(2) 0.44248(15) 0.0335(6) Uani 1 1 d . . . . .
C1 C 0.76913(19) 0.3563(2) 0.47877(15) 0.0329(6) Uani 1 1 d . . . . .
C22 C 0.6406(2) 0.2364(2) 0.50567(16) 0.0340(6) Uani 1 1 d . . . . .
H22 H 0.6101 0.2255 0.5513 0.041 Uiso 1 1 calc R U . . .
C9 C 0.7777(2) 0.6257(2) 0.47573(17) 0.0378(6) Uani 1 1 d . . . . .
C2 C 0.8136(2) 0.2483(2) 0.49677(15) 0.0334(6) Uani 1 1 d . . . . .
C5 C 0.9063(2) 0.3972(2) 0.41741(16) 0.0391(6) Uani 1 1 d . . . . .
C28 C 0.8923(2) 0.3196(3) 0.71268(17) 0.0436(7) Uani 1 1 d . . . . .
H28 H 0.9480 0.3046 0.6923 0.052 Uiso 1 1 calc R U . . .
C4 C 0.9476(2) 0.2892(3) 0.43604(17) 0.0433(7) Uani 1 1 d . . . . .
H4 H 1.0058 0.2673 0.4206 0.052 Uiso 1 1 calc R U . . .
C3 C 0.9023(2) 0.2134(2) 0.47784(17) 0.0413(7) Uani 1 1 d . . . . .
H3 H 0.9308 0.1414 0.4926 0.050 Uiso 1 1 calc R U . . .
C7 C 0.9392(2) 0.4925(3) 0.37124(17) 0.0470(7) Uani 1 1 d . . . . .
H7A H 0.9402 0.4680 0.3156 0.056 Uiso 1 1 calc R U . . .
H7B H 1.0098 0.5210 0.4052 0.056 Uiso 1 1 calc R U . . .
C24 C 0.7258(2) 0.2643(3) 0.72945(18) 0.0439(7) Uani 1 1 d . . . . .
H24 H 0.6706 0.2120 0.7203 0.053 Uiso 1 1 calc R U . . .
C21 C 0.5663(2) 0.1847(2) 0.42222(17) 0.0388(6) Uani 1 1 d . . . . .
C14 C 0.5769(2) 0.4273(3) 0.4349(2) 0.0487(7) Uani 1 1 d . . . . .
H14 H 0.5727 0.5050 0.4412 0.058 Uiso 1 1 calc R U . . .
C16 C 0.5014(2) 0.2555(3) 0.35620(17) 0.0471(7) Uani 1 1 d . . . . .
C27 C 0.8927(3) 0.4175(3) 0.75828(18) 0.0497(7) Uani 1 1 d . . . . .
H27 H 0.9490 0.4689 0.7693 0.060 Uiso 1 1 calc R U . . .
C8 C 0.8528(2) 0.5827(3) 0.36082(19) 0.0494(7) Uani 1 1 d . . . . .
H8A H 0.8851 0.6567 0.3759 0.059 Uiso 1 1 calc R U . . .
H8B H 0.8029 0.5847 0.3019 0.059 Uiso 1 1 calc R U . . .
C26 C 0.8088(3) 0.4380(2) 0.78716(17) 0.0456(7) Uani 1 1 d . . . . .
C15 C 0.5033(2) 0.3769(3) 0.3689(2) 0.0534(8) Uani 1 1 d . . . . .
H15 H 0.4512 0.4209 0.3294 0.064 Uiso 1 1 calc R U . . .
C25 C 0.7262(2) 0.3624(3) 0.77466(18) 0.0478(7) Uani 1 1 d . . . . .
H25 H 0.6715 0.3770 0.7963 0.057 Uiso 1 1 calc R U . . .
C20 C 0.5600(2) 0.0695(3) 0.4119(2) 0.0489(7) Uani 1 1 d . . . . .
H20 H 0.6001 0.0230 0.4570 0.059 Uiso 1 1 calc R U . . .
C10 C 0.7554(3) 0.6650(3) 0.6022(2) 0.0576(8) Uani 1 1 d . . . . .
H10 H 0.7507 0.6414 0.6544 0.069 Uiso 1 1 calc R U . . .
C17 C 0.4354(2) 0.2042(4) 0.2797(2) 0.0635(10) Uani 1 1 d . . . . .
H17 H 0.3923 0.2490 0.2349 0.076 Uiso 1 1 calc R U . . .
C12 C 0.7508(3) 0.8075(3) 0.5045(3) 0.0721(11) Uani 1 1 d . . . . .
H12 H 0.7450 0.8836 0.4897 0.086 Uiso 1 1 calc R U . . .
C11 C 0.7436(4) 0.7773(3) 0.5826(3) 0.0725(11) Uani 1 1 d . . . . .
H11 H 0.7315 0.8302 0.6197 0.087 Uiso 1 1 calc R U . . .
C19 C 0.4945(3) 0.0216(3) 0.3351(2) 0.0656(10) Uani 1 1 d . . . . .
H19 H 0.4923 -0.0564 0.3283 0.079 Uiso 1 1 calc R U . . .
C18 C 0.4335(3) 0.0888(4) 0.2698(2) 0.0711(11) Uani 1 1 d . . . . .
H18 H 0.3901 0.0566 0.2182 0.085 Uiso 1 1 calc R U . . .
 
 
_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 O1 1.424(2) . ?
S1 O2 1.432(2) . ?
S1 N4 1.649(2) . ?
S1 C23 1.761(3) . ?
Cl1 C26 1.741(3) . ?
N4 C2 1.447(3) . ?
N4 C22 1.505(3) . ?
N1 C9 1.375(3) . ?
N1 C6 1.417(3) . ?
N1 C8 1.485(3) . ?
N2 C10 1.334(4) . ?
N2 C9 1.338(3) . ?
N3 C12 1.335(5) . ?
N3 C9 1.341(4) . ?
C13 C14 1.501(4) . ?
C13 C1 1.520(4) . ?
C13 C22 1.552(4) . ?
C13 H13 0.9800 . ?
C23 C28 1.385(4) . ?
C23 C24 1.388(4) . ?
C6 C1 1.395(4) . ?
C6 C5 1.404(4) . ?
C1 C2 1.396(4) . ?
C22 C21 1.520(3) . ?
C22 H22 0.9800 . ?
C2 C3 1.382(4) . ?
C5 C4 1.382(4) . ?
C5 C7 1.510(4) . ?
C28 C27 1.382(4) . ?
C28 H28 0.9300 . ?
C4 C3 1.391(4) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C7 C8 1.532(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C24 C25 1.381(4) . ?
C24 H24 0.9300 . ?
C21 C20 1.373(4) . ?
C21 C16 1.409(4) . ?
C14 C15 1.328(4) . ?
C14 H14 0.9300 . ?
C16 C17 1.403(4) . ?
C16 C15 1.451(5) . ?
C27 C26 1.377(4) . ?
C27 H27 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C26 C25 1.374(4) . ?
C15 H15 0.9300 . ?
C25 H25 0.9300 . ?
C20 C19 1.388(4) . ?
C20 H20 0.9300 . ?
C10 C11 1.365(5) . ?
C10 H10 0.9300 . ?
C17 C18 1.375(5) . ?
C17 H17 0.9300 . ?
C12 C11 1.375(5) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C19 C18 1.360(6) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
 
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 S1 O2 120.39(14) . . ?
O1 S1 N4 106.60(12) . . ?
O2 S1 N4 105.99(12) . . ?
O1 S1 C23 109.21(13) . . ?
O2 S1 C23 107.95(13) . . ?
N4 S1 C23 105.75(11) . . ?
C2 N4 C22 105.79(19) . . ?
C2 N4 S1 119.09(16) . . ?
C22 N4 S1 117.46(17) . . ?
C9 N1 C6 123.2(2) . . ?
C9 N1 C8 120.7(2) . . ?
C6 N1 C8 108.3(2) . . ?
C10 N2 C9 115.6(3) . . ?
C12 N3 C9 115.2(3) . . ?
C14 C13 C1 114.5(2) . . ?
C14 C13 C22 113.3(2) . . ?
C1 C13 C22 101.3(2) . . ?
C14 C13 H13 109.1 . . ?
C1 C13 H13 109.1 . . ?
C22 C13 H13 109.1 . . ?
C28 C23 C24 120.8(3) . . ?
C28 C23 S1 119.2(2) . . ?
C24 C23 S1 119.8(2) . . ?
C1 C6 C5 119.7(2) . . ?
C1 C6 N1 129.7(2) . . ?
C5 C6 N1 110.5(2) . . ?
C6 C1 C2 117.2(2) . . ?
C6 C1 C13 132.4(2) . . ?
C2 C1 C13 110.3(2) . . ?
N4 C22 C21 108.3(2) . . ?
N4 C22 C13 104.6(2) . . ?
C21 C22 C13 114.9(2) . . ?
N4 C22 H22 109.6 . . ?
C21 C22 H22 109.6 . . ?
C13 C22 H22 109.6 . . ?
N2 C9 N3 126.3(3) . . ?
N2 C9 N1 117.5(2) . . ?
N3 C9 N1 116.2(2) . . ?
C3 C2 C1 123.7(2) . . ?
C3 C2 N4 126.1(2) . . ?
C1 C2 N4 110.0(2) . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 C7 129.9(3) . . ?
C6 C5 C7 109.1(3) . . ?
C27 C28 C23 119.4(3) . . ?
C27 C28 H28 120.3 . . ?
C23 C28 H28 120.3 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C2 C3 C4 117.9(3) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C5 C7 C8 104.0(2) . . ?
C5 C7 H7A 111.0 . . ?
C8 C7 H7A 111.0 . . ?
C5 C7 H7B 111.0 . . ?
C8 C7 H7B 111.0 . . ?
H7A C7 H7B 109.0 . . ?
C25 C24 C23 119.7(3) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C20 C21 C16 120.0(3) . . ?
C20 C21 C22 120.4(3) . . ?
C16 C21 C22 119.6(3) . . ?
C15 C14 C13 122.4(3) . . ?
C15 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
C17 C16 C21 117.6(3) . . ?
C17 C16 C15 122.3(3) . . ?
C21 C16 C15 120.1(3) . . ?
C26 C27 C28 119.1(3) . . ?
C26 C27 H27 120.4 . . ?
C28 C27 H27 120.4 . . ?
N1 C8 C7 105.2(2) . . ?
N1 C8 H8A 110.7 . . ?
C7 C8 H8A 110.7 . . ?
N1 C8 H8B 110.7 . . ?
C7 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C25 C26 C27 122.1(3) . . ?
C25 C26 Cl1 118.7(2) . . ?
C27 C26 Cl1 119.2(2) . . ?
C14 C15 C16 122.4(3) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C26 C25 C24 118.9(3) . . ?
C26 C25 H25 120.6 . . ?
C24 C25 H25 120.6 . . ?
C21 C20 C19 120.7(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
N2 C10 C11 123.4(3) . . ?
N2 C10 H10 118.3 . . ?
C11 C10 H10 118.3 . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
N3 C12 C11 123.4(3) . . ?
N3 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
C10 C11 C12 116.0(3) . . ?
C10 C11 H11 122.0 . . ?
C12 C11 H11 122.0 . . ?
C18 C19 C20 120.0(4) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
 
_refine_diff_density_max    0.279
_refine_diff_density_min   -0.376
_refine_diff_density_rms    0.051



