#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/54/2205400.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_2205400
loop_
_publ_author_name
'Kırılmış, Cumhur'
'Koca, Murat'
'Arıcı, Cengiz'
'W. Heinemann, Frank'
_publ_section_title
3-Cyclohexyl-4-(3-methyl-3-phenylcyclobutyl)-1,3-thiazole-2(3H)-thione
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1176
_journal_page_last               o1177
_journal_paper_doi               10.1107/S160053680500930X
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C20 H25 N S2'
_chemical_formula_moiety         'C20 H25 N S2'
_chemical_formula_sum            'C20 H25 N S2'
_chemical_formula_weight         343.53
_chemical_name_systematic
;
3-Cyclohexyl-4-(3-methyl-3-phenylcyclobutyl)-1,3-thiazole-2(3H)-thione
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9686(8)
_cell_length_b                   12.2843(8)
_cell_length_c                   14.7707(3)
_cell_measurement_reflns_used    264
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      6.0
_cell_volume                     1808.78(19)
_computing_cell_refinement       'EVALCCD (Bruker--Nonius, 2002)'
_computing_data_collection       'COLLECT (Bruker--Nonius, 2002)'
_computing_data_reduction        EVALCCD
_computing_molecular_graphics
;
SHELXTL and ORTEP-3 (Farrugia, 1997)
;
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 2001)'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius KappaCCD'
_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  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            27385
_diffrn_reflns_theta_full        27.86
_diffrn_reflns_theta_max         27.86
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.294
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.209
_refine_ls_abs_structure_details 'Flack (1983), 1856 Freidel pairs'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4306
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0314
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.039P)²+0.201P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                3828
_reflns_number_total             4306
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at6001.cif
_cod_data_source_block           I
_cod_original_cell_volume        1808.8(2)
_cod_database_code               2205400
_cod_database_fobs_code          2205400
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_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
_atom_site_type_symbol
S1 0.15976(4) 0.68713(3) 0.01800(3) 0.01436(10) Uani d 1 S
S2 -0.11815(4) 0.65353(3) 0.08574(3) 0.01770(11) Uani d 1 S
N1 0.11752(14) 0.58259(10) 0.16288(9) 0.0101(3) Uani d 1 N
C1 0.44514(18) 0.19189(14) 0.11652(11) 0.0166(4) Uani d 1 C
C2 0.4973(2) 0.11228(15) 0.05902(12) 0.0192(4) Uani d 1 C
C3 0.62952(19) 0.11879(14) 0.03051(12) 0.0188(4) Uani d 1 C
C4 0.70939(18) 0.20476(15) 0.05863(11) 0.0176(4) Uani d 1 C
C5 0.65786(18) 0.28444(14) 0.11541(11) 0.0152(4) Uani d 1 C
C6 0.52396(17) 0.27913(13) 0.14524(11) 0.0117(3) Uani d 1 C
C7 0.47087(16) 0.36513(13) 0.20865(11) 0.0121(3) Uani d 1 C
C8 0.52228(19) 0.34469(17) 0.30462(12) 0.0179(4) Uani d 1 C
C9 0.48996(17) 0.48595(14) 0.17840(12) 0.0132(3) Uani d 1 C
C10 0.31703(17) 0.38502(14) 0.20951(12) 0.0133(3) Uani d 1 C
C11 0.34450(17) 0.51059(13) 0.20972(11) 0.0112(3) Uani d 1 C
C12 0.25767(16) 0.57763(13) 0.14866(11) 0.0103(3) Uani d 1 C
C13 0.29573(17) 0.63181(13) 0.07376(11) 0.0128(3) Uani d 1 C
C14 0.04775(17) 0.63528(13) 0.09680(11) 0.0133(3) Uani d 1 C
C15 0.05573(17) 0.53817(13) 0.24697(11) 0.0114(3) Uani d 1 C
C16 -0.00798(19) 0.62749(14) 0.30485(12) 0.0156(4) Uani d 1 C
C17 -0.0537(2) 0.57754(16) 0.39491(13) 0.0207(4) Uani d 1 C
C18 -0.1497(2) 0.48230(15) 0.37902(14) 0.0235(4) Uani d 1 C
C19 -0.08497(18) 0.39573(15) 0.31933(13) 0.0191(4) Uani d 1 C
C20 -0.03935(19) 0.44332(14) 0.22870(12) 0.0161(4) Uani d 1 C
H1 0.348(2) 0.1830(19) 0.1421(15) 0.040 Uiso d 1 H
H2 0.443(2) 0.052(2) 0.0419(16) 0.040 Uiso d 1 H
H3 0.664(2) 0.0652(19) -0.0092(17) 0.040 Uiso d 1 H
H4 0.795(3) 0.214(2) 0.0379(16) 0.040 Uiso d 1 H
H5 0.712(2) 0.346(2) 0.1360(16) 0.040 Uiso d 1 H
H8A 0.481(2) 0.399(2) 0.3464(17) 0.040 Uiso d 1 H
H8B 0.619(3) 0.3418(19) 0.3058(15) 0.040 Uiso d 1 H
H8C 0.492(2) 0.273(2) 0.3297(16) 0.040 Uiso d 1 H
H9A 0.498(2) 0.4902(19) 0.1122(17) 0.040 Uiso d 1 H
H9B 0.563(2) 0.527(2) 0.2108(15) 0.040 Uiso d 1 H
H10A 0.268(2) 0.357(2) 0.2625(17) 0.040 Uiso d 1 H
H10B 0.270(2) 0.363(2) 0.1546(17) 0.040 Uiso d 1 H
H11 0.345(2) 0.5446(18) 0.2735(16) 0.040 Uiso d 1 H
H13 0.383(3) 0.6400(19) 0.0477(15) 0.040 Uiso d 1 H
H15 0.133(3) 0.505(2) 0.2786(16) 0.040 Uiso d 1 H
H16A 0.063(2) 0.685(2) 0.3177(15) 0.040 Uiso d 1 H
H16B -0.086(2) 0.657(2) 0.2728(16) 0.040 Uiso d 1 H
H17A -0.092(2) 0.636(2) 0.4335(16) 0.040 Uiso d 1 H
H17B 0.022(3) 0.554(2) 0.4261(17) 0.040 Uiso d 1 H
H18A -0.175(3) 0.4497(19) 0.4348(17) 0.040 Uiso d 1 H
H18B -0.233(2) 0.511(2) 0.3472(17) 0.040 Uiso d 1 H
H19A -0.006(3) 0.363(2) 0.3497(16) 0.040 Uiso d 1 H
H19B -0.149(2) 0.3312(19) 0.3059(15) 0.040 Uiso d 1 H
H20A -0.117(3) 0.471(2) 0.1941(15) 0.040 Uiso d 1 H
H20B 0.002(3) 0.385(2) 0.1922(16) 0.040 Uiso d 1 H
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'
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
_geom_angle_publ_flag
C13 S1 C14 92.34(8) yes
C14 N1 C12 114.74(14) ?
C14 N1 C15 124.08(14) ?
C12 N1 C15 121.09(13) ?
C6 C1 C2 120.89(17) ?
C6 C1 H1 119.5(13) ?
C2 C1 H1 119.5(13) ?
C3 C2 C1 119.92(17) ?
C3 C2 H2 120.4(15) ?
C1 C2 H2 119.6(15) ?
C2 C3 C4 119.94(17) ?
C2 C3 H3 119.8(15) ?
C4 C3 H3 120.3(15) ?
C3 C4 C5 120.39(17) ?
C3 C4 H4 122.2(16) ?
C5 C4 H4 117.3(16) ?
C4 C5 C6 120.51(16) ?
C4 C5 H5 122.2(14) ?
C6 C5 H5 117.3(14) ?
C1 C6 C5 118.34(16) ?
C1 C6 C7 121.97(15) ?
C5 C6 C7 119.66(15) ?
C6 C7 C8 110.09(13) ?
C6 C7 C10 117.51(14) ?
C8 C7 C10 110.45(14) ?
C6 C7 C9 116.45(14) ?
C8 C7 C9 112.38(14) ?
C10 C7 C9 88.47(12) ?
C7 C8 H8A 109.2(14) ?
C7 C8 H8B 111.0(13) ?
H8A C8 H8B 115(2) ?
C7 C8 H8C 112.8(14) ?
H8A C8 H8C 103.3(19) ?
H8B C8 H8C 105(2) ?
C11 C9 C7 89.21(12) ?
C11 C9 H9A 111.5(14) ?
C7 C9 H9A 110.2(14) ?
C11 C9 H9B 115.7(13) ?
C7 C9 H9B 115.6(14) ?
H9A C9 H9B 112.6(19) ?
C7 C10 C11 88.99(12) ?
C7 C10 H10A 116.3(14) ?
C11 C10 H10A 115.4(15) ?
C7 C10 H10B 115.0(14) ?
C11 C10 H10B 111.0(15) ?
H10A C10 H10B 109.1(19) ?
C12 C11 C9 117.91(14) ?
C12 C11 C10 116.07(14) ?
C9 C11 C10 88.32(12) ?
C12 C11 H11 109.2(13) ?
C9 C11 H11 110.5(14) ?
C10 C11 H11 113.6(13) ?
C13 C12 N1 112.29(15) ?
C13 C12 C11 127.19(15) ?
N1 C12 C11 120.36(14) ?
C12 C13 S1 111.50(10) yes
C12 C13 H13 129.7(14) ?
S1 C13 H13 118.7(14) ?
N1 C14 S2 129.60(10) yes
N1 C14 S1 109.10(10) yes
S2 C14 S1 121.40(10) yes
N1 C15 C20 112.90(14) ?
N1 C15 C16 112.02(13) ?
C20 C15 C16 112.87(14) ?
N1 C15 H15 102.9(14) ?
C20 C15 H15 104.9(14) ?
C16 C15 H15 110.5(14) ?
C15 C16 C17 108.74(14) ?
C15 C16 H16A 108.3(13) ?
C17 C16 H16A 108.9(13) ?
C15 C16 H16B 109.1(14) ?
C17 C16 H16B 109.6(14) ?
H16A C16 H16B 112.2(19) ?
C18 C17 C16 111.02(16) ?
C18 C17 H17A 113.7(13) ?
C16 C17 H17A 108.7(13) ?
C18 C17 H17B 110.3(15) ?
C16 C17 H17B 108.2(15) ?
H17A C17 H17B 105(2) ?
C19 C18 C17 110.94(15) ?
C19 C18 H18A 108.6(15) ?
C17 C18 H18A 110.7(14) ?
C19 C18 H18B 108.5(14) ?
C17 C18 H18B 108.7(14) ?
H18A C18 H18B 109(2) ?
C18 C19 C20 111.42(15) ?
C18 C19 H19A 111.0(14) ?
C20 C19 H19A 108.2(14) ?
C18 C19 H19B 112.7(13) ?
C20 C19 H19B 107.9(13) ?
H19A C19 H19B 105.4(18) ?
C15 C20 C19 108.77(15) ?
C15 C20 H20A 108.5(15) ?
C19 C20 H20A 110.5(14) ?
C15 C20 H20B 113.1(15) ?
C19 C20 H20B 109.1(14) ?
H20A C20 H20B 107(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C13 1.725(2) yes
S1 C14 1.734(2) yes
S2 C14 1.677(2) yes
N1 C14 1.362(2) ?
N1 C12 1.414(2) ?
N1 C15 1.490(2) ?
C1 C6 1.395(2) ?
C1 C2 1.396(3) ?
C1 H1 1.05(2) ?
C2 C3 1.386(3) ?
C2 H2 0.95(3) ?
C3 C4 1.386(3) ?
C3 H3 0.95(3) ?
C4 C5 1.388(2) ?
C4 H4 0.91(2) ?
C5 C6 1.407(2) ?
C5 H5 0.98(2) ?
C6 C7 1.508(2) ?
C7 C8 1.528(2) ?
C7 C10 1.553(2) ?
C7 C9 1.562(2) ?
C8 H8A 0.99(3) ?
C8 H8B 0.96(2) ?
C8 H8C 1.00(3) ?
C9 C11 1.552(2) ?
C9 H9A 0.98(2) ?
C9 H9B 1.01(3) ?
C10 C11 1.567(2) ?
C10 H10A 0.98(2) ?
C10 H10B 0.97(3) ?
C11 C12 1.497(2) ?
C11 H11 1.03(2) ?
C12 C13 1.346(2) ?
C13 H13 0.96(3) ?
C15 C20 1.526(2) ?
C15 C16 1.529(2) ?
C15 H15 0.98(3) ?
C16 C17 1.534(2) ?
C16 H16A 1.02(3) ?
C16 H16B 0.98(2) ?
C17 C18 1.530(3) ?
C17 H17A 1.00(3) ?
C17 H17B 0.93(3) ?
C18 C19 1.525(3) ?
C18 H18A 0.95(2) ?
C18 H18B 1.01(3) ?
C19 C20 1.530(3) ?
C19 H19A 1.00(3) ?
C19 H19B 1.04(2) ?
C20 H20A 0.99(3) ?
C20 H20B 0.98(3) ?
