#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/11/2221187.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_2221187
loop_
_publ_author_name
'Rahmani, Hossein'
'Pirelahi, Hooshang'
'Ng, Seik Weng'
_publ_section_title
;
 4-Methyl-2,4,6-triphenyl-4H-thiopyran
;
_journal_coeditor_code           SJ2578
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o603
_journal_paper_doi               10.1107/S1600536809005911
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C24 H20 S'
_chemical_formula_moiety         'C24 H20 S'
_chemical_formula_sum            'C24 H20 S'
_chemical_formula_weight         340.46
_chemical_name_systematic
;
4-Methyl-2,4,6-triphenyl-4H-thiopyran
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 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                 118.9870(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8737(2)
_cell_length_b                   22.5282(4)
_cell_length_c                   9.2288(2)
_cell_measurement_reflns_used    4067
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      2.5
_cell_volume                     1795.67(6)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      115(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8464
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.81
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.183
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.175
_refine_ls_abs_structure_details 'Flack (1983), 1825 Friedel pairs'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0401P)²+0.2571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0720
_reflns_number_gt                3698
_reflns_number_total             3883
_reflns_threshold_expression     I>σ(I)
_cod_data_source_file            sj2578.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2221187
_cod_database_fobs_code          2221187
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'
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_disorder_assembly
_atom_site_disorder_group
S S1 0.49977(4) 0.892322(17) 0.49963(4) 0.01993(9) Uani d . 1 . .
C C1 0.48277(17) 0.87133(6) 0.67575(18) 0.0169(3) Uani d . 1 . .
C C2 0.37550(18) 0.83350(7) 0.66660(19) 0.0197(3) Uani d . 1 . .
H H2 0.3740 0.8259 0.7671 0.024 Uiso calc R 1 . .
C C3 0.25547(17) 0.80107(7) 0.51476(19) 0.0187(3) Uani d . 1 . .
C C4 0.22225(18) 0.83423(7) 0.35828(18) 0.0180(3) Uani d . 1 . .
H H4 0.1228 0.8283 0.2651 0.022 Uiso calc R 1 . .
C C5 0.31709(16) 0.87086(6) 0.33675(17) 0.0156(3) Uani d . 1 . .
C C6 0.3178(2) 0.73921(7) 0.5054(2) 0.0252(4) Uani d . 1 . .
H H6A 0.3487 0.7178 0.6092 0.038 Uiso calc R 1 . .
H H6B 0.4075 0.7437 0.4879 0.038 Uiso calc R 1 . .
H H6C 0.2366 0.7168 0.4131 0.038 Uiso calc R 1 . .
C C7 0.59735(17) 0.90088(7) 0.83149(19) 0.0174(3) Uani d . 1 . .
C C8 0.55816(18) 0.91435(7) 0.95401(19) 0.0210(3) Uani d . 1 . .
H H8 0.4585 0.9041 0.9379 0.025 Uiso calc R 1 . .
C C9 0.66275(19) 0.94253(7) 1.0990(2) 0.0241(3) Uani d . 1 . .
H H9 0.6341 0.9517 1.1810 0.029 Uiso calc R 1 . .
C C10 0.8091(2) 0.95738(7) 1.1249(2) 0.0236(4) Uani d . 1 . .
H H10 0.8809 0.9766 1.2245 0.028 Uiso calc R 1 . .
C C11 0.84996(18) 0.94407(7) 1.0045(2) 0.0237(3) Uani d . 1 . .
H H11 0.9503 0.9540 1.0221 0.028 Uiso calc R 1 . .
C C12 0.74509(18) 0.91643(7) 0.85877(19) 0.0207(3) Uani d . 1 . .
H H12 0.7738 0.9079 0.7765 0.025 Uiso calc R 1 . .
C C13 0.10640(17) 0.79667(7) 0.52855(18) 0.0183(3) Uani d . 1 . .
C C14 0.0894(2) 0.75238(8) 0.6233(2) 0.0255(3) Uani d . 1 . .
H H14 0.1679 0.7231 0.6742 0.031 Uiso calc R 1 . .
C C15 -0.0402(2) 0.75009(8) 0.6451(2) 0.0294(4) Uani d . 1 . .
H H15 -0.0487 0.7198 0.7118 0.035 Uiso calc R 1 . .
C C16 -0.1572(2) 0.79169(8) 0.5702(2) 0.0284(4) Uani d . 1 . .
H H16 -0.2465 0.7899 0.5836 0.034 Uiso calc R 1 . .
C C17 -0.14174(19) 0.83609(8) 0.47516(19) 0.0257(4) Uani d . 1 . .
H H17 -0.2212 0.8649 0.4232 0.031 Uiso calc R 1 . .
C C18 -0.01103(19) 0.83879(7) 0.45533(18) 0.0222(3) Uani d . 1 . .
H H18 -0.0016 0.8698 0.3910 0.027 Uiso calc R 1 . .
C C19 0.27339(17) 0.89872(7) 0.17441(18) 0.0165(3) Uani d . 1 . .
C C20 0.18705(18) 0.86626(7) 0.02926(18) 0.0191(3) Uani d . 1 . .
H H20 0.1658 0.8255 0.0359 0.023 Uiso calc R 1 . .
C C21 0.13179(19) 0.89302(7) -0.1250(2) 0.0222(3) Uani d . 1 . .
H H21 0.0729 0.8706 -0.2230 0.027 Uiso calc R 1 . .
C C22 0.16242(19) 0.95233(8) -0.1358(2) 0.0238(4) Uani d . 1 . .
H H22 0.1232 0.9708 -0.2412 0.029 Uiso calc R 1 . .
C C23 0.25068(19) 0.98482(7) 0.0078(2) 0.0242(3) Uani d . 1 . .
H H23 0.2722 1.0255 0.0005 0.029 Uiso calc R 1 . .
C C24 0.30752(18) 0.95805(7) 0.16187(18) 0.0192(3) Uani d . 1 . .
H H24 0.3700 0.9802 0.2594 0.023 Uiso calc R 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'
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
_geom_angle_publ_flag
C5 S1 C1 . . 101.27(7) ?
C2 C1 C7 . . 123.89(14) ?
C2 C1 S1 . . 122.53(12) ?
C7 C1 S1 . . 113.57(11) ?
C1 C2 C3 . . 127.59(14) ?
C1 C2 H2 . . 116.2 ?
C3 C2 H2 . . 116.2 ?
C4 C3 C2 . . 110.82(12) ?
C4 C3 C13 . . 109.66(12) ?
C2 C3 C13 . . 107.77(13) ?
C4 C3 C6 . . 107.47(13) ?
C2 C3 C6 . . 109.47(13) ?
C13 C3 C6 . . 111.67(12) ?
C5 C4 C3 . . 127.18(13) ?
C5 C4 H4 . . 116.4 ?
C3 C4 H4 . . 116.4 ?
C4 C5 C19 . . 122.09(13) ?
C4 C5 S1 . . 122.96(11) ?
C19 C5 S1 . . 114.91(11) ?
C3 C6 H6A . . 109.5 ?
C3 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C3 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C8 C7 C12 . . 118.32(14) ?
C8 C7 C1 . . 120.06(14) ?
C12 C7 C1 . . 121.62(14) ?
C9 C8 C7 . . 120.86(15) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C10 . . 120.22(15) ?
C8 C9 H9 . . 119.9 ?
C10 C9 H9 . . 119.9 ?
C11 C10 C9 . . 119.59(15) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C12 C11 C10 . . 120.30(15) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C7 . . 120.71(15) ?
C11 C12 H12 . . 119.6 ?
C7 C12 H12 . . 119.6 ?
C14 C13 C18 . . 117.92(14) ?
C14 C13 C3 . . 120.65(14) ?
C18 C13 C3 . . 121.32(14) ?
C15 C14 C13 . . 121.22(16) ?
C15 C14 H14 . . 119.4 ?
C13 C14 H14 . . 119.4 ?
C16 C15 C14 . . 120.43(16) ?
C16 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
C15 C16 C17 . . 118.94(16) ?
C15 C16 H16 . . 120.5 ?
C17 C16 H16 . . 120.5 ?
C16 C17 C18 . . 120.56(16) ?
C16 C17 H17 . . 119.7 ?
C18 C17 H17 . . 119.7 ?
C17 C18 C13 . . 120.92(15) ?
C17 C18 H18 . . 119.5 ?
C13 C18 H18 . . 119.5 ?
C20 C19 C24 . . 118.78(14) ?
C20 C19 C5 . . 119.41(13) ?
C24 C19 C5 . . 121.68(13) ?
C21 C20 C19 . . 120.60(15) ?
C21 C20 H20 . . 119.7 ?
C19 C20 H20 . . 119.7 ?
C22 C21 C20 . . 120.09(15) ?
C22 C21 H21 . . 120.0 ?
C20 C21 H21 . . 120.0 ?
C21 C22 C23 . . 119.82(15) ?
C21 C22 H22 . . 120.1 ?
C23 C22 H22 . . 120.1 ?
C24 C23 C22 . . 120.22(15) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C23 C24 C19 . . 120.44(14) ?
C23 C24 H24 . . 119.8 ?
C19 C24 H24 . . 119.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C5 . 1.7661(14) ?
S1 C1 . 1.7772(15) ?
C1 C2 . 1.330(2) ?
C1 C7 . 1.488(2) ?
C2 C3 . 1.514(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.514(2) ?
C3 C13 . 1.541(2) ?
C3 C6 . 1.543(2) ?
C4 C5 . 1.333(2) ?
C4 H4 . 0.9500 ?
C5 C19 . 1.483(2) ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 C8 . 1.394(2) ?
C7 C12 . 1.399(2) ?
C8 C9 . 1.386(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.387(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.386(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.386(2) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 C14 . 1.390(2) ?
C13 C18 . 1.393(2) ?
C14 C15 . 1.390(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.384(3) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.386(3) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.390(2) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 C20 . 1.396(2) ?
C19 C24 . 1.397(2) ?
C20 C21 . 1.391(2) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.384(2) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.390(2) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.388(2) ?
C23 H23 . 0.9500 ?
C24 H24 . 0.9500 ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 S1 C1 C2 . . . . 17.61(15) ?
C5 S1 C1 C7 . . . . -161.33(11) ?
C7 C1 C2 C3 . . . . -179.48(15) ?
S1 C1 C2 C3 . . . . 1.7(2) ?
C1 C2 C3 C4 . . . . -24.4(2) ?
C1 C2 C3 C13 . . . . -144.35(16) ?
C1 C2 C3 C6 . . . . 94.01(19) ?
C2 C3 C4 C5 . . . . 26.5(2) ?
C13 C3 C4 C5 . . . . 145.30(15) ?
C6 C3 C4 C5 . . . . -93.12(19) ?
C3 C4 C5 C19 . . . . 177.18(14) ?
C3 C4 C5 S1 . . . . -5.5(2) ?
C1 S1 C5 C4 . . . . -15.81(15) ?
C1 S1 C5 C19 . . . . 161.67(11) ?
C2 C1 C7 C8 . . . . -31.3(2) ?
S1 C1 C7 C8 . . . . 147.59(12) ?
C2 C1 C7 C12 . . . . 149.37(16) ?
S1 C1 C7 C12 . . . . -31.71(19) ?
C12 C7 C8 C9 . . . . 0.1(2) ?
C1 C7 C8 C9 . . . . -179.21(15) ?
C7 C8 C9 C10 . . . . -0.5(3) ?
C8 C9 C10 C11 . . . . 0.2(3) ?
C9 C10 C11 C12 . . . . 0.4(3) ?
C10 C11 C12 C7 . . . . -0.8(3) ?
C8 C7 C12 C11 . . . . 0.5(2) ?
C1 C7 C12 C11 . . . . 179.82(15) ?
C4 C3 C13 C14 . . . . 157.18(14) ?
C2 C3 C13 C14 . . . . -82.11(17) ?
C6 C3 C13 C14 . . . . 38.2(2) ?
C4 C3 C13 C18 . . . . -26.78(19) ?
C2 C3 C13 C18 . . . . 93.93(16) ?
C6 C3 C13 C18 . . . . -145.80(14) ?
C18 C13 C14 C15 . . . . -0.2(2) ?
C3 C13 C14 C15 . . . . 175.99(16) ?
C13 C14 C15 C16 . . . . 1.0(3) ?
C14 C15 C16 C17 . . . . -0.9(3) ?
C15 C16 C17 C18 . . . . 0.0(3) ?
C16 C17 C18 C13 . . . . 0.8(2) ?
C14 C13 C18 C17 . . . . -0.7(2) ?
C3 C13 C18 C17 . . . . -176.85(14) ?
C4 C5 C19 C20 . . . . -37.1(2) ?
S1 C5 C19 C20 . . . . 145.37(12) ?
C4 C5 C19 C24 . . . . 138.58(16) ?
S1 C5 C19 C24 . . . . -38.92(19) ?
C24 C19 C20 C21 . . . . -2.1(2) ?
C5 C19 C20 C21 . . . . 173.78(14) ?
C19 C20 C21 C22 . . . . 0.1(2) ?
C20 C21 C22 C23 . . . . 1.0(2) ?
C21 C22 C23 C24 . . . . -0.3(2) ?
C22 C23 C24 C19 . . . . -1.7(2) ?
C20 C19 C24 C23 . . . . 2.8(2) ?
C5 C19 C24 C23 . . . . -172.93(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741786
