#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/55/2235578.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_2235578
loop_
_publ_author_name
'El-Emam, Ali A.'
'Al-Deeb, Omar A.'
'Al-Turkistani, Abdulghafoor A.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 2-[(4-Chlorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-(phenylsulfanyl)pyrimidine-5-carbonitrile
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2055
_journal_page_last               o2056
_journal_paper_doi               10.1107/S1600536812025810
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C22 H20 Cl N3 S2'
_chemical_formula_moiety         'C22 H20 Cl N3 S2'
_chemical_formula_sum            'C22 H20 Cl N3 S2'
_chemical_formula_weight         425.98
_chemical_name_systematic
;
2-[(4-Chlorobenzyl)sulfanyl]-4-(2-methylpropyl)-6-(phenylsulfanyl)pyrimidine-
5-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.5590(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7771(2)
_cell_length_b                   8.49610(10)
_cell_length_c                   18.5878(2)
_cell_measurement_reflns_used    8707
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      76.4387
_cell_measurement_theta_min      3.7634
_cell_volume                     2156.82(5)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg,
2006)
;
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
'Agilent SuperNova Dual diffractometer with Atlas detector'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0183
_diffrn_reflns_av_sigmaI/netI    0.0148
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15819
_diffrn_reflns_theta_full        76.64
_diffrn_reflns_theta_max         76.64
_diffrn_reflns_theta_min         4.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.466
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.61059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2012)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.461
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4512
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0411
_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)+(0.0576P)²+0.7026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1166
_reflns_number_gt                4113
_reflns_number_total             4512
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2554.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235578
_cod_database_fobs_code          2235578
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.54678(4) 0.70944(6) 0.73269(3) 0.06701(18) Uani d . 1 1
S S2 0.49600(3) 0.22299(6) 0.55116(3) 0.06114(16) Uani d . 1 1
Cl Cl1 0.03279(4) 0.03665(9) 0.36870(4) 0.0973(2) Uani d . 1 1
N N1 0.53172(10) 0.46391(16) 0.64164(8) 0.0477(3) Uani d . 1 1
N N2 0.66645(10) 0.30012(16) 0.61951(8) 0.0505(3) Uani d . 1 1
N N3 0.80681(16) 0.6954(3) 0.78507(12) 0.0912(7) Uani d . 1 1
C C1 0.57237(12) 0.34328(19) 0.61056(9) 0.0466(3) Uani d . 1 1
C C2 0.59250(12) 0.55031(19) 0.68709(9) 0.0474(4) Uani d . 1 1
C C3 0.69249(12) 0.5177(2) 0.70000(9) 0.0483(4) Uani d . 1 1
C C4 0.72740(11) 0.3888(2) 0.66431(9) 0.0466(4) Uani d . 1 1
C C5 0.83447(12) 0.3509(2) 0.67331(10) 0.0541(4) Uani d . 1 1
H H5A 0.8431 0.2392 0.6652 0.065 Uiso calc R 1 1
H H5B 0.8631 0.3749 0.7226 0.065 Uiso calc R 1 1
C C6 0.88789(13) 0.4457(2) 0.61966(11) 0.0578(4) Uani d . 1 1
H H6 0.8652 0.5549 0.6198 0.069 Uiso calc R 1 1
C C7 0.86479(17) 0.3820(3) 0.54342(12) 0.0774(6) Uani d . 1 1
H H7A 0.8969 0.4452 0.5109 0.116 Uiso calc R 1 1
H H7B 0.7953 0.3850 0.5289 0.116 Uiso calc R 1 1
H H7C 0.8874 0.2753 0.5421 0.116 Uiso calc R 1 1
C C8 0.99730(16) 0.4440(4) 0.64422(16) 0.0962(9) Uani d . 1 1
H H8A 1.0300 0.5050 0.6112 0.144 Uiso calc R 1 1
H H8B 1.0208 0.3375 0.6450 0.144 Uiso calc R 1 1
H H8C 1.0104 0.4882 0.6920 0.144 Uiso calc R 1 1
C C9 0.75677(14) 0.6152(3) 0.74776(11) 0.0616(5) Uani d . 1 1
C C10 0.42250(13) 0.7160(2) 0.69300(10) 0.0532(4) Uani d . 1 1
C C11 0.39312(19) 0.8248(3) 0.63982(13) 0.0737(6) Uani d . 1 1
H H11 0.4385 0.8918 0.6229 0.088 Uiso calc R 1 1
C C12 0.2950(2) 0.8330(3) 0.61170(15) 0.0912(8) Uani d . 1 1
H H12 0.2744 0.9069 0.5760 0.109 Uiso calc R 1 1
C C13 0.22799(19) 0.7338(3) 0.63589(14) 0.0811(7) Uani d . 1 1
H H13 0.1623 0.7404 0.6166 0.097 Uiso calc R 1 1
C C14 0.25756(15) 0.6249(3) 0.68832(13) 0.0698(5) Uani d . 1 1
H H14 0.2122 0.5564 0.7042 0.084 Uiso calc R 1 1
C C15 0.35460(14) 0.6169(2) 0.71770(11) 0.0592(4) Uani d . 1 1
H H15 0.3744 0.5445 0.7542 0.071 Uiso calc R 1 1
C C16 0.37985(15) 0.3241(3) 0.55162(13) 0.0707(6) Uani d . 1 1
H H16A 0.3653 0.3319 0.6011 0.085 Uiso calc R 1 1
H H16B 0.3852 0.4301 0.5331 0.085 Uiso calc R 1 1
C C17 0.29733(13) 0.2398(2) 0.50618(10) 0.0530(4) Uani d . 1 1
C C18 0.20723(15) 0.2336(3) 0.53091(11) 0.0636(5) Uani d . 1 1
H H18 0.2008 0.2733 0.5767 0.076 Uiso calc R 1 1
C C19 0.12653(15) 0.1699(3) 0.48935(12) 0.0672(5) Uani d . 1 1
H H19 0.0663 0.1673 0.5068 0.081 Uiso calc R 1 1
C C20 0.13592(14) 0.1106(2) 0.42242(11) 0.0604(5) Uani d . 1 1
C C21 0.22472(16) 0.1110(3) 0.39687(11) 0.0685(5) Uani d . 1 1
H H21 0.2309 0.0679 0.3517 0.082 Uiso calc R 1 1
C C22 0.30503(15) 0.1760(3) 0.43874(11) 0.0636(5) Uani d . 1 1
H H22 0.3653 0.1769 0.4213 0.076 Uiso calc R 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C2 S1 C10 102.20(8)
C1 S2 C16 100.23(9)
C2 N1 C1 115.71(14)
C4 N2 C1 116.30(14)
N1 C1 N2 127.73(15)
N1 C1 S2 118.00(12)
N2 C1 S2 114.27(12)
N1 C2 C3 121.65(15)
N1 C2 S1 119.73(12)
C3 C2 S1 118.62(13)
C2 C3 C4 117.89(15)
C2 C3 C9 120.51(16)
C4 C3 C9 121.59(16)
N2 C4 C3 120.71(15)
N2 C4 C5 118.54(15)
C3 C4 C5 120.72(16)
C4 C5 C6 111.24(15)
C4 C5 H5A 109.4
C6 C5 H5A 109.4
C4 C5 H5B 109.4
C6 C5 H5B 109.4
H5A C5 H5B 108.0
C7 C6 C8 110.93(18)
C7 C6 C5 111.11(17)
C8 C6 C5 109.91(18)
C7 C6 H6 108.3
C8 C6 H6 108.3
C5 C6 H6 108.3
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C6 C8 H8A 109.5
C6 C8 H8B 109.5
H8A C8 H8B 109.5
C6 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N3 C9 C3 178.5(3)
C11 C10 C15 120.0(2)
C11 C10 S1 119.80(16)
C15 C10 S1 120.09(15)
C10 C11 C12 119.1(2)
C10 C11 H11 120.5
C12 C11 H11 120.5
C13 C12 C11 120.8(2)
C13 C12 H12 119.6
C11 C12 H12 119.6
C14 C13 C12 120.0(2)
C14 C13 H13 120.0
C12 C13 H13 120.0
C13 C14 C15 120.0(2)
C13 C14 H14 120.0
C15 C14 H14 120.0
C14 C15 C10 120.1(2)
C14 C15 H15 119.9
C10 C15 H15 119.9
C17 C16 S2 111.90(14)
C17 C16 H16A 109.2
S2 C16 H16A 109.2
C17 C16 H16B 109.2
S2 C16 H16B 109.2
H16A C16 H16B 107.9
C18 C17 C22 117.82(18)
C18 C17 C16 118.50(17)
C22 C17 C16 123.56(18)
C19 C18 C17 121.52(18)
C19 C18 H18 119.2
C17 C18 H18 119.2
C20 C19 C18 119.33(19)
C20 C19 H19 120.3
C18 C19 H19 120.3
C19 C20 C21 120.78(19)
C19 C20 Cl1 119.19(16)
C21 C20 Cl1 120.02(16)
C20 C21 C22 119.44(19)
C20 C21 H21 120.3
C22 C21 H21 120.3
C21 C22 C17 121.07(18)
C21 C22 H22 119.5
C17 C22 H22 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.7559(16)
S1 C10 1.774(2)
S2 C1 1.7508(17)
S2 C16 1.817(2)
Cl1 C20 1.743(2)
N1 C2 1.330(2)
N1 C1 1.335(2)
N2 C4 1.335(2)
N2 C1 1.336(2)
N3 C9 1.138(3)
C2 C3 1.395(2)
C3 C4 1.398(2)
C3 C9 1.432(2)
C4 C5 1.498(2)
C5 C6 1.542(2)
C5 H5A 0.9700
C5 H5B 0.9700
C6 C7 1.511(3)
C6 C8 1.516(3)
C6 H6 0.9800
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C10 C11 1.375(3)
C10 C15 1.382(3)
C11 C12 1.386(4)
C11 H11 0.9300
C12 C13 1.369(4)
C12 H12 0.9300
C13 C14 1.366(4)
C13 H13 0.9300
C14 C15 1.378(3)
C14 H14 0.9300
C15 H15 0.9300
C16 C17 1.505(3)
C16 H16A 0.9700
C16 H16B 0.9700
C17 C18 1.380(3)
C17 C22 1.382(3)
C18 C19 1.378(3)
C18 H18 0.9300
C19 C20 1.364(3)
C19 H19 0.9300
C20 C21 1.369(3)
C21 C22 1.381(3)
C21 H21 0.9300
C22 H22 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
C6 H6 Cg1 3_666 0.98 2.92 3.789(2) 148
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
C2 N1 C1 N2 -0.4(3)
C2 N1 C1 S2 179.05(12)
C4 N2 C1 N1 -0.7(3)
C4 N2 C1 S2 179.89(12)
C16 S2 C1 N1 2.66(17)
C16 S2 C1 N2 -177.85(15)
C1 N1 C2 C3 1.2(2)
C1 N1 C2 S1 -178.59(12)
C10 S1 C2 N1 -5.74(16)
C10 S1 C2 C3 174.49(14)
N1 C2 C3 C4 -0.9(2)
S1 C2 C3 C4 178.83(12)
N1 C2 C3 C9 178.32(17)
S1 C2 C3 C9 -1.9(2)
C1 N2 C4 C3 0.9(2)
C1 N2 C4 C5 -176.83(15)
C2 C3 C4 N2 -0.2(2)
C9 C3 C4 N2 -179.41(16)
C2 C3 C4 C5 177.52(15)
C9 C3 C4 C5 -1.7(3)
N2 C4 C5 C6 92.3(2)
C3 C4 C5 C6 -85.4(2)
C4 C5 C6 C7 -73.9(2)
C4 C5 C6 C8 162.9(2)
C2 S1 C10 C11 -100.58(16)
C2 S1 C10 C15 82.29(16)
C15 C10 C11 C12 0.0(3)
S1 C10 C11 C12 -177.11(19)
C10 C11 C12 C13 -0.5(4)
C11 C12 C13 C14 0.0(4)
C12 C13 C14 C15 1.1(4)
C13 C14 C15 C10 -1.6(3)
C11 C10 C15 C14 1.0(3)
S1 C10 C15 C14 178.16(15)
C1 S2 C16 C17 -177.46(16)
S2 C16 C17 C18 141.33(18)
S2 C16 C17 C22 -42.7(3)
C22 C17 C18 C19 -1.7(3)
C16 C17 C18 C19 174.6(2)
C17 C18 C19 C20 0.4(3)
C18 C19 C20 C21 1.3(3)
C18 C19 C20 Cl1 -177.69(17)
C19 C20 C21 C22 -1.7(3)
Cl1 C20 C21 C22 177.29(18)
C20 C21 C22 C17 0.4(3)
C18 C17 C22 C21 1.2(3)
C16 C17 C22 C21 -174.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657902
