#------------------------------------------------------------------------------
#$Date: 2018-09-29 05:09:18 +0300 (Sat, 29 Sep 2018) $
#$Revision: 211228 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/26/2242654.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_2242654
loop_
_publ_author_name
'Yennawar, Hemant P.'
'Moyer, Quentin J.'
'Silverberg, Lee J.'
_publ_section_title
;
 Crystal structure of
 meso-3,3'-(1,4-phenylene)bis(2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one)
;
_journal_coeditor_code           HB7772
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1497
_journal_page_last               1499
_journal_paper_doi               10.1107/S2056989018013397
_journal_volume                  74
_journal_year                    2018
_chemical_formula_iupac          'C26 H24 N2 O2 S2'
_chemical_formula_moiety         'C26 H24 N2 O2 S2'
_chemical_formula_sum            'C26 H24 N2 O2 S2'
_chemical_formula_weight         460.59
_chemical_name_systematic
meso-3,3'-(1,4-Phenylene)bis(2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.289(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.080(2)
_cell_length_b                   13.017(4)
_cell_length_c                   12.093(3)
_cell_measurement_reflns_used    1747
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.152
_cell_measurement_theta_min      2.309
_cell_volume                     1102.9(5)
_computing_cell_refinement
;
SAINT  (Bruker, 2001)
;
_computing_data_collection
;
SMART  (Bruker, 2001)
;
_computing_data_reduction
;
SAINT  (Bruker, 2001)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7575
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.31
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_T_max  0.9
_exptl_absorpt_correction_T_min  0.857198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 20014)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0560
_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)+(0.0717P)²+0.4464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1485
_reflns_number_gt                2055
_reflns_number_total             2757
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7772sup1.cif
_cod_data_source_block           I
_cod_database_code               2242654
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -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_occupancy
C C1 0.9688(3) 0.29893(15) 0.21227(18) 0.0388(5) Uani d 1
H H1 1.0585 0.2852 0.1594 0.047 Uiso calc 1
C C2 0.6918(3) 0.41602(17) 0.20879(17) 0.0392(5) Uani d 1
C C3 0.5997(4) 0.3422(2) 0.2815(2) 0.0588(7) Uani d 1
H H3A 0.5923 0.3776 0.3514 0.071 Uiso calc 1
H H3B 0.4694 0.3322 0.2457 0.071 Uiso calc 1
C C4 0.6802(4) 0.2374(2) 0.3114(2) 0.0601(7) Uani d 1
H H4A 0.5760 0.1906 0.3187 0.072 Uiso calc 1
H H4B 0.7608 0.2410 0.3833 0.072 Uiso calc 1
C C5 1.0882(3) 0.31690(16) 0.32526(18) 0.0387(5) Uani d 1
C C6 1.1926(3) 0.2367(2) 0.3796(2) 0.0523(6) Uani d 1
H H6 1.1855 0.1714 0.3480 0.063 Uiso calc 1
C C7 1.3066(3) 0.2534(3) 0.4800(2) 0.0654(8) Uani d 1
H H7 1.3765 0.1993 0.5156 0.078 Uiso calc 1
C C8 1.3185(4) 0.3491(3) 0.5283(2) 0.0739(9) Uani d 1
H H8 1.3950 0.3597 0.5965 0.089 Uiso calc 1
C C9 1.2166(4) 0.4288(3) 0.4751(2) 0.0675(8) Uani d 1
H H9 1.2248 0.4939 0.5069 0.081 Uiso calc 1
C C10 1.1016(3) 0.4123(2) 0.37427(19) 0.0502(6) Uani d 1
H H10 1.0321 0.4668 0.3390 0.060 Uiso calc 1
C C11 0.9278(3) 0.44770(14) 0.08461(15) 0.0317(4) Uani d 1
C C12 1.1198(3) 0.47343(16) 0.09557(16) 0.0350(4) Uani d 1
H H12 1.2007 0.4556 0.1602 0.042 Uiso calc 1
C C13 0.8087(3) 0.47470(15) -0.01124(16) 0.0347(4) Uani d 1
H H13 0.6798 0.4579 -0.0191 0.042 Uiso calc 1
N N1 0.8566(2) 0.38859(13) 0.16985(14) 0.0355(4) Uani d 1
O O1 0.6121(2) 0.49719(13) 0.18357(15) 0.0539(4) Uani d 1
S S1 0.81637(9) 0.18725(5) 0.21024(6) 0.0574(2) Uani d 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C5 C1 H1 . . 106.6
C5 C1 S1 . . 112.95(14)
N1 C1 H1 . . 106.6
N1 C1 C5 . . 113.37(17)
N1 C1 S1 . . 110.10(13)
S1 C1 H1 . . 106.6
N1 C2 C3 . . 119.70(19)
O1 C2 C3 . . 118.33(19)
O1 C2 N1 . . 121.92(19)
C2 C3 H3A . . 106.7
C2 C3 H3B . . 106.7
H3A C3 H3B . . 106.6
C4 C3 C2 . . 122.4(2)
C4 C3 H3A . . 106.7
C4 C3 H3B . . 106.7
C3 C4 H4A . . 109.0
C3 C4 H4B . . 109.0
C3 C4 S1 . . 113.01(18)
H4A C4 H4B . . 107.8
S1 C4 H4A . . 109.0
S1 C4 H4B . . 109.0
C6 C5 C1 . . 120.0(2)
C10 C5 C1 . . 121.50(18)
C10 C5 C6 . . 118.5(2)
C5 C6 H6 . . 119.9
C7 C6 C5 . . 120.2(3)
C7 C6 H6 . . 119.9
C6 C7 H7 . . 119.6
C8 C7 C6 . . 120.8(2)
C8 C7 H7 . . 119.6
C7 C8 H8 . . 120.3
C9 C8 C7 . . 119.4(3)
C9 C8 H8 . . 120.3
C8 C9 H9 . . 120.0
C8 C9 C10 . . 120.1(3)
C10 C9 H9 . . 120.0
C5 C10 C9 . . 121.0(2)
C5 C10 H10 . . 119.5
C9 C10 H10 . . 119.5
C12 C11 N1 . . 120.09(16)
C13 C11 C12 . . 119.42(17)
C13 C11 N1 . . 120.40(17)
C11 C12 H12 . . 119.8
C13 C12 C11 3_765 . 120.44(17)
C13 C12 H12 3_765 . 119.8
C11 C13 C12 . 3_765 120.14(17)
C11 C13 H13 . . 119.9
C12 C13 H13 3_765 . 119.9
C2 N1 C1 . . 122.35(17)
C2 N1 C11 . . 120.86(16)
C11 N1 C1 . . 116.80(15)
C4 S1 C1 . . 94.42(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 H1 . 0.9800
C1 C5 . 1.518(3)
C1 N1 . 1.462(2)
C1 S1 . 1.809(2)
C2 C3 . 1.512(3)
C2 N1 . 1.367(3)
C2 O1 . 1.216(3)
C3 H3A . 0.9700
C3 H3B . 0.9700
C3 C4 . 1.502(4)
C4 H4A . 0.9700
C4 H4B . 0.9700
C4 S1 . 1.787(3)
C5 C6 . 1.389(3)
C5 C10 . 1.374(3)
C6 H6 . 0.9300
C6 C7 . 1.375(4)
C7 H7 . 0.9300
C7 C8 . 1.373(5)
C8 H8 . 0.9300
C8 C9 . 1.370(4)
C9 H9 . 0.9300
C9 C10 . 1.382(3)
C10 H10 . 0.9300
C11 C12 . 1.388(3)
C11 C13 . 1.377(3)
C11 N1 . 1.435(2)
C12 H12 . 0.9300
C12 C13 3_765 1.379(3)
C13 C12 3_765 1.379(3)
C13 H13 . 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
C13 H13 O1 3_665 0.93 2.72 3.401(3) 131
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_site_symmetry_4
_geom_torsion
C1 C5 C6 C7 . 177.6(2)
C1 C5 C10 C9 . -177.4(2)
C2 C3 C4 S1 . -26.3(3)
C3 C2 N1 C1 . -11.9(3)
C3 C2 N1 C11 . 168.2(2)
C3 C4 S1 C1 . 53.0(2)
C5 C1 N1 C2 . -77.3(2)
C5 C1 N1 C11 . 102.54(19)
C5 C1 S1 C4 . 62.97(17)
C5 C6 C7 C8 . 0.3(4)
C6 C5 C10 C9 . 0.2(3)
C6 C7 C8 C9 . -0.5(4)
C7 C8 C9 C10 . 0.6(4)
C8 C9 C10 C5 . -0.5(4)
C10 C5 C6 C7 . -0.1(3)
C12 C11 C13 C12 3_765 0.2(3)
C12 C11 N1 C1 . -45.4(2)
C12 C11 N1 C2 . 134.4(2)
C13 C11 C12 C13 3_765 -0.2(3)
C13 C11 N1 C1 . 131.14(19)
C13 C11 N1 C2 . -49.0(3)
N1 C1 C5 C6 . 175.76(18)
N1 C1 C5 C10 . -6.6(3)
N1 C1 S1 C4 . -64.88(16)
N1 C2 C3 C4 . -1.4(4)
N1 C11 C12 C13 3_765 176.39(18)
N1 C11 C13 C12 3_765 -176.38(18)
O1 C2 C3 C4 . 176.1(3)
O1 C2 N1 C1 . 170.7(2)
O1 C2 N1 C11 . -9.2(3)
S1 C1 C5 C6 . 49.6(2)
S1 C1 C5 C10 . -132.72(19)
S1 C1 N1 C2 . 50.3(2)
S1 C1 N1 C11 . -129.85(15)

_cod_database_fobs_code 2242654
