#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/92/2239245.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2239245
loop_
_publ_author_name
'Yennawar, Hemant P.'
'Bendinsky, Ryan V.'
'Coyle, David J.'
'Cali, Aaron S.'
'Silverberg, Lee J.'
_publ_section_title
;
 2,3-Diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one
;
_journal_coeditor_code           FY2112
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o465
_journal_paper_doi               10.1107/S1600536814005881
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C20 H15 N O S'
_chemical_formula_moiety         'C20 H15 N O S'
_chemical_formula_sum            'C20 H15 N O S'
_chemical_formula_weight         317.39
_chemical_name_systematic
;
2,3-Diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.736(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.799(4)
_cell_length_b                   9.606(3)
_cell_length_c                   22.492(6)
_cell_measurement_reflns_used    4538
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.022
_cell_measurement_theta_min      2.536
_cell_volume                     3160.3(16)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'XSHELL in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 8.34
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            14747
_diffrn_reflns_theta_full        28.39
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_correction_T_min  0.9634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.251
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0506
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0565P)²+1.8423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1205
_refine_ls_wR_factor_ref         0.1268
_reflns_number_gt                3300
_reflns_number_total             3956
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fy2112sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        3160.1(15)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2239245
_cod_database_fobs_code          2239245
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'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.03935(11) 0.32561(17) 0.11547(7) 0.0434(4) Uani d . 1 1
C C2 0.01411(11) 0.46594(17) 0.13594(7) 0.0434(4) Uani d . 1 1
C C3 0.04910(12) 0.58978(17) 0.11600(7) 0.0460(4) Uani d . 1 1
C C4 0.18665(11) 0.42745(15) 0.09649(7) 0.0406(3) Uani d . 1 1
H H4 0.2301 0.4022 0.0695 0.049 Uiso calc R 1 1
C C5 0.24251(10) 0.45006(15) 0.15831(7) 0.0377(3) Uani d . 1 1
C C6 0.23025(12) 0.37177(17) 0.20814(8) 0.0469(4) Uani d . 1 1
H H6 0.1848 0.3041 0.2048 0.056 Uiso calc R 1 1
C C7 0.28512(13) 0.3933(2) 0.26298(8) 0.0557(4) Uani d . 1 1
H H7 0.2759 0.3408 0.2963 0.067 Uiso calc R 1 1
C C8 0.35351(13) 0.4925(2) 0.26842(9) 0.0559(4) Uani d . 1 1
H H8 0.3903 0.5069 0.3052 0.067 Uiso calc R 1 1
C C9 0.36669(12) 0.56958(17) 0.21908(9) 0.0519(4) Uani d . 1 1
H H9 0.4131 0.6357 0.2225 0.062 Uiso calc R 1 1
C C10 0.31166(11) 0.54979(16) 0.16442(8) 0.0442(4) Uani d . 1 1
H H10 0.3208 0.6034 0.1314 0.053 Uiso calc R 1 1
C C11 0.14103(11) 0.18738(16) 0.06409(7) 0.0393(3) Uani d . 1 1
C C12 0.21265(16) 0.1052(2) 0.08852(9) 0.0657(6) Uani d . 1 1
H H12 0.2492 0.1317 0.1241 0.079 Uiso calc R 1 1
C C13 0.23063(18) -0.0177(2) 0.06018(10) 0.0759(7) Uani d . 1 1
H H13 0.2795 -0.0733 0.0767 0.091 Uiso calc R 1 1
C C14 0.17703(15) -0.05742(19) 0.00829(9) 0.0592(5) Uani d . 1 1
H H14 0.1882 -0.1412 -0.0100 0.071 Uiso calc R 1 1
C C15 0.10730(15) 0.0256(2) -0.01663(9) 0.0670(6) Uani d . 1 1
H H15 0.0715 -0.0005 -0.0525 0.080 Uiso calc R 1 1
C C16 0.08922(14) 0.1488(2) 0.01100(8) 0.0603(5) Uani d . 1 1
H H16 0.0417 0.2057 -0.0065 0.072 Uiso calc R 1 1
C C17 -0.05168(12) 0.4728(2) 0.17424(8) 0.0514(4) Uani d . 1 1
H H17 -0.0753 0.3909 0.1877 0.062 Uiso calc R 1 1
C C18 -0.08209(14) 0.5990(2) 0.19226(9) 0.0619(5) Uani d . 1 1
H H18 -0.1253 0.6023 0.2182 0.074 Uiso calc R 1 1
C C19 -0.04820(14) 0.7204(2) 0.17166(10) 0.0660(6) Uani d . 1 1
H H19 -0.0696 0.8056 0.1834 0.079 Uiso calc R 1 1
C C20 0.01695(14) 0.7175(2) 0.13392(9) 0.0583(5) Uani d . 1 1
H H20 0.0394 0.8002 0.1204 0.070 Uiso calc R 1 1
N N1 0.12016(9) 0.31448(13) 0.09313(6) 0.0408(3) Uani d . 1 1
O O1 -0.01007(9) 0.22507(14) 0.11818(6) 0.0617(4) Uani d . 1 1
S S1 0.13067(3) 0.58704(5) 0.06672(2) 0.05412(16) Uani d . 1 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 N1 121.37(15)
O1 C1 C2 121.40(15)
N1 C1 C2 117.23(14)
C17 C2 C3 119.01(16)
C17 C2 C1 117.65(15)
C3 C2 C1 123.24(15)
C20 C3 C2 119.70(17)
C20 C3 S1 119.44(14)
C2 C3 S1 120.83(13)
N1 C4 C5 114.97(12)
N1 C4 S1 109.96(11)
C5 C4 S1 111.69(10)
N1 C4 H4 106.6
C5 C4 H4 106.6
S1 C4 H4 106.6
C6 C5 C10 118.58(15)
C6 C5 C4 122.85(14)
C10 C5 C4 118.51(14)
C5 C6 C7 120.57(16)
C5 C6 H6 119.7
C7 C6 H6 119.7
C8 C7 C6 120.27(17)
C8 C7 H7 119.9
C6 C7 H7 119.9
C9 C8 C7 119.51(17)
C9 C8 H8 120.2
C7 C8 H8 120.2
C8 C9 C10 120.57(17)
C8 C9 H9 119.7
C10 C9 H9 119.7
C9 C10 C5 120.50(16)
C9 C10 H10 119.8
C5 C10 H10 119.8
C12 C11 C16 119.43(16)
C12 C11 N1 120.90(15)
C16 C11 N1 119.66(15)
C11 C12 C13 119.86(18)
C11 C12 H12 120.1
C13 C12 H12 120.1
C14 C13 C12 120.3(2)
C14 C13 H13 119.8
C12 C13 H13 119.8
C15 C14 C13 119.79(18)
C15 C14 H14 120.1
C13 C14 H14 120.1
C14 C15 C16 120.32(18)
C14 C15 H15 119.8
C16 C15 H15 119.8
C11 C16 C15 120.21(18)
C11 C16 H16 119.9
C15 C16 H16 119.9
C18 C17 C2 120.88(19)
C18 C17 H17 119.6
C2 C17 H17 119.6
C17 C18 C19 119.67(19)
C17 C18 H18 120.2
C19 C18 H18 120.2
C18 C19 C20 120.95(18)
C18 C19 H19 119.5
C20 C19 H19 119.5
C19 C20 C3 119.77(19)
C19 C20 H20 120.1
C3 C20 H20 120.1
C1 N1 C11 119.46(13)
C1 N1 C4 122.85(13)
C11 N1 C4 117.68(12)
C3 S1 C4 95.64(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.218(2)
C1 N1 1.370(2)
C1 C2 1.490(2)
C2 C17 1.396(2)
C2 C3 1.398(2)
C3 C20 1.397(2)
C3 S1 1.7587(19)
C4 N1 1.4590(19)
C4 C5 1.521(2)
C4 S1 1.8211(16)
C4 H4 0.9800
C5 C6 1.384(2)
C5 C10 1.393(2)
C6 C7 1.385(2)
C6 H6 0.9300
C7 C8 1.382(3)
C7 H7 0.9300
C8 C9 1.373(3)
C8 H8 0.9300
C9 C10 1.381(2)
C9 H9 0.9300
C10 H10 0.9300
C11 C12 1.368(2)
C11 C16 1.368(2)
C11 N1 1.4401(19)
C12 C13 1.386(3)
C12 H12 0.9300
C13 C14 1.362(3)
C13 H13 0.9300
C14 C15 1.356(3)
C14 H14 0.9300
C15 C16 1.382(3)
C15 H15 0.9300
C16 H16 0.9300
C17 C18 1.376(3)
C17 H17 0.9300
C18 C19 1.377(3)
C18 H18 0.9300
C19 C20 1.378(3)
C19 H19 0.9300
C20 H20 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C10 H10 O1 3 0.93 2.82 3.422(2) 123.6
C15 H15 O1 5 0.93 2.69 3.477(2) 142.4
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
O1 C1 C2 C17 18.8(2)
N1 C1 C2 C17 -161.54(14)
O1 C1 C2 C3 -157.41(17)
N1 C1 C2 C3 22.2(2)
C17 C2 C3 C20 -0.9(2)
C1 C2 C3 C20 175.31(15)
C17 C2 C3 S1 -178.93(12)
C1 C2 C3 S1 -2.7(2)
N1 C4 C5 C6 -1.3(2)
S1 C4 C5 C6 124.86(14)
N1 C4 C5 C10 175.80(13)
S1 C4 C5 C10 -58.01(16)
C10 C5 C6 C7 0.6(2)
C4 C5 C6 C7 177.72(15)
C5 C6 C7 C8 -0.7(3)
C6 C7 C8 C9 0.0(3)
C7 C8 C9 C10 0.7(3)
C8 C9 C10 C5 -0.7(3)
C6 C5 C10 C9 0.1(2)
C4 C5 C10 C9 -177.16(14)
C16 C11 C12 C13 -1.6(3)
N1 C11 C12 C13 179.11(19)
C11 C12 C13 C14 -0.4(4)
C12 C13 C14 C15 1.8(4)
C13 C14 C15 C16 -1.3(3)
C12 C11 C16 C15 2.1(3)
N1 C11 C16 C15 -178.59(18)
C14 C15 C16 C11 -0.6(3)
C3 C2 C17 C18 0.1(3)
C1 C2 C17 C18 -176.35(16)
C2 C17 C18 C19 0.9(3)
C17 C18 C19 C20 -1.0(3)
C18 C19 C20 C3 0.2(3)
C2 C3 C20 C19 0.8(3)
S1 C3 C20 C19 178.82(14)
O1 C1 N1 C11 9.4(2)
C2 C1 N1 C11 -170.25(13)
O1 C1 N1 C4 -171.62(16)
C2 C1 N1 C4 8.8(2)
C12 C11 N1 C1 -114.62(19)
C16 C11 N1 C1 66.1(2)
C12 C11 N1 C4 66.3(2)
C16 C11 N1 C4 -113.00(18)
C5 C4 N1 C1 75.41(18)
S1 C4 N1 C1 -51.67(17)
C5 C4 N1 C11 -105.55(15)
S1 C4 N1 C11 127.37(12)
C20 C3 S1 C4 148.70(14)
C2 C3 S1 C4 -33.26(15)
N1 C4 S1 C3 56.83(12)
C5 C4 S1 C3 -72.06(12)
