#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/33/2223336.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_2223336
loop_
_publ_author_name
'El Ashry, El Sayed H.'
'Amer, Mohammed R.'
'Raza Shah, Muhammad'
'Ng, Seik Weng'
_publ_section_title
;
 n-Butyl
 2-(2,4-dichloroanilino)-4,4-dimethyl-6-oxocyclohex-1-enecarbodithioate
;
_journal_coeditor_code           CI2904
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2459
_journal_paper_doi               10.1107/S1600536809036320
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H23 Cl2 N O S2'
_chemical_formula_moiety         'C19 H23 Cl2 N O S2'
_chemical_formula_sum            'C19 H23 Cl2 N O S2'
_chemical_formula_weight         416.40
_chemical_name_systematic
;
n-Butyl
2-(2,4-dichloroanilino)-4,4-dimethyl-6-oxocyclohex-1-enecarbodithioate
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.3310(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.03210(10)
_cell_length_b                   19.4422(2)
_cell_length_c                   11.47000(10)
_cell_measurement_reflns_used    9957
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.5
_cell_volume                     1981.52(4)
_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      123(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  0.0162
_diffrn_reflns_av_sigmaI/netI    0.0129
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18747
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.09
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.546
_exptl_absorpt_correction_T_max  0.9474
_exptl_absorpt_correction_T_min  0.8533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.250
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0251
_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)+(0.0405P)²+0.9836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                4279
_reflns_number_total             4554
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2904.cif
_cod_data_source_block           I
_cod_original_cell_volume        1981.52(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223336
_cod_database_fobs_code          2223336
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_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.66246(3) 0.420713(17) 0.99199(3) 0.02548(8) Uani d . 1 . .
Cl Cl2 1.25630(3) 0.391875(17) 1.00782(3) 0.02572(8) Uani d . 1 . .
S S1 0.17044(3) 0.547076(14) 0.56447(2) 0.01521(7) Uani d . 1 . .
S S2 0.45310(3) 0.595199(14) 0.71292(3) 0.01818(8) Uani d . 1 . .
O O1 0.18119(12) 0.41970(5) 0.52118(12) 0.0435(3) Uani d . 1 . .
N N1 0.65717(11) 0.47990(5) 0.74995(8) 0.01551(19) Uani d . 1 . .
H H1 0.625(2) 0.5237(10) 0.7584(16) 0.033(4) Uiso d . 1 . .
C C1 0.31311(14) 0.40793(6) 0.56335(11) 0.0194(2) Uani d . 1 . .
C C2 0.37252(13) 0.33742(6) 0.54278(10) 0.0176(2) Uani d . 1 . .
H H2A 0.4118 0.3381 0.4676 0.021 Uiso calc R 1 . .
H H2B 0.2878 0.3044 0.5331 0.021 Uiso calc R 1 . .
C C3 0.49613(12) 0.31158(6) 0.64090(10) 0.0150(2) Uani d . 1 . .
C C4 0.61567(12) 0.36787(6) 0.66192(10) 0.0163(2) Uani d . 1 . .
H H4A 0.6925 0.3547 0.7312 0.020 Uiso calc R 1 . .
H H4B 0.6662 0.3698 0.5922 0.020 Uiso calc R 1 . .
C C5 0.55899(12) 0.43880(6) 0.68327(9) 0.0133(2) Uani d . 1 . .
C C6 0.41136(12) 0.46044(6) 0.63000(10) 0.0141(2) Uani d . 1 . .
C C7 0.56586(14) 0.24599(6) 0.60044(11) 0.0203(2) Uani d . 1 . .
H H7A 0.6051 0.2554 0.5277 0.030 Uiso calc R 1 . .
H H7B 0.4890 0.2100 0.5851 0.030 Uiso calc R 1 . .
H H7C 0.6482 0.2306 0.6626 0.030 Uiso calc R 1 . .
C C8 0.43521(15) 0.29707(7) 0.75460(11) 0.0246(3) Uani d . 1 . .
H H8A 0.3590 0.2607 0.7397 0.037 Uiso calc R 1 . .
H H8B 0.3898 0.3390 0.7800 0.037 Uiso calc R 1 . .
H H8C 0.5178 0.2822 0.8170 0.037 Uiso calc R 1 . .
C C9 0.80208(12) 0.45912(6) 0.81146(10) 0.0144(2) Uani d . 1 . .
C C10 0.81793(13) 0.43077(6) 0.92496(10) 0.0160(2) Uani d . 1 . .
C C11 0.95775(13) 0.40992(6) 0.98561(10) 0.0171(2) Uani d . 1 . .
H H11 0.9681 0.3902 1.0624 0.021 Uiso calc R 1 . .
C C12 1.08177(13) 0.41848(6) 0.93158(10) 0.0171(2) Uani d . 1 . .
C C13 1.07029(13) 0.44805(6) 0.82040(10) 0.0187(2) Uani d . 1 . .
H H13 1.1572 0.4543 0.7856 0.022 Uiso calc R 1 . .
C C14 0.92928(13) 0.46846(6) 0.76063(10) 0.0169(2) Uani d . 1 . .
H H14 0.9198 0.4889 0.6845 0.020 Uiso calc R 1 . .
C C15 0.35496(12) 0.53004(6) 0.63903(9) 0.0140(2) Uani d . 1 . .
C C16 0.14330(13) 0.63819(6) 0.58501(10) 0.0162(2) Uani d . 1 . .
H H16A 0.2411 0.6618 0.5885 0.019 Uiso calc R 1 . .
H H16B 0.0737 0.6561 0.5150 0.019 Uiso calc R 1 . .
C C17 0.08095(13) 0.65650(6) 0.69585(10) 0.0169(2) Uani d . 1 . .
H H17A 0.1575 0.6462 0.7669 0.020 Uiso calc R 1 . .
H H17B -0.0089 0.6280 0.6994 0.020 Uiso calc R 1 . .
C C18 0.03800(14) 0.73269(6) 0.69634(11) 0.0226(2) Uani d . 1 . .
H H18A 0.1254 0.7609 0.6846 0.027 Uiso calc R 1 . .
H H18B -0.0451 0.7418 0.6292 0.027 Uiso calc R 1 . .
C C19 -0.01100(17) 0.75431(7) 0.81137(13) 0.0308(3) Uani d . 1 . .
H H19A -0.0374 0.8033 0.8074 0.046 Uiso calc R 1 . .
H H19B 0.0716 0.7464 0.8780 0.046 Uiso calc R 1 . .
H H19C -0.0988 0.7272 0.8227 0.046 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'
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'
Cl Cl 0.1484 0.1585 '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
C15 S1 C16 . . 105.02(5) ?
C5 N1 C9 . . 124.86(10) ?
C5 N1 H1 . . 115.5(11) ?
C9 N1 H1 . . 119.6(11) ?
O1 C1 C6 . . 121.90(11) ?
O1 C1 C2 . . 117.19(11) ?
C6 C1 C2 . . 120.90(10) ?
C1 C2 C3 . . 114.80(9) ?
C1 C2 H2A . . 108.6 ?
C3 C2 H2A . . 108.6 ?
C1 C2 H2B . . 108.6 ?
C3 C2 H2B . . 108.6 ?
H2A C2 H2B . . 107.5 ?
C2 C3 C4 . . 106.54(9) ?
C2 C3 C8 . . 111.29(10) ?
C4 C3 C8 . . 110.49(10) ?
C2 C3 C7 . . 109.76(9) ?
C4 C3 C7 . . 109.11(9) ?
C8 C3 C7 . . 109.58(10) ?
C5 C4 C3 . . 115.52(9) ?
C5 C4 H4A . . 108.4 ?
C3 C4 H4A . . 108.4 ?
C5 C4 H4B . . 108.4 ?
C3 C4 H4B . . 108.4 ?
H4A C4 H4B . . 107.5 ?
N1 C5 C6 . . 123.03(10) ?
N1 C5 C4 . . 115.65(10) ?
C6 C5 C4 . . 121.26(10) ?
C5 C6 C15 . . 123.74(10) ?
C5 C6 C1 . . 116.59(10) ?
C15 C6 C1 . . 119.67(10) ?
C3 C7 H7A . . 109.5 ?
C3 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C3 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C3 C8 H8A . . 109.5 ?
C3 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C3 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C14 C9 C10 . . 119.20(10) ?
C14 C9 N1 . . 120.57(10) ?
C10 C9 N1 . . 120.21(10) ?
C11 C10 C9 . . 120.93(10) ?
C11 C10 Cl1 . . 118.85(9) ?
C9 C10 Cl1 . . 120.22(9) ?
C12 C11 C10 . . 118.49(10) ?
C12 C11 H11 . . 120.8 ?
C10 C11 H11 . . 120.8 ?
C11 C12 C13 . . 121.94(11) ?
C11 C12 Cl2 . . 118.20(9) ?
C13 C12 Cl2 . . 119.85(9) ?
C12 C13 C14 . . 118.85(11) ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C9 C14 C13 . . 120.55(11) ?
C9 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C6 C15 S2 . . 125.12(8) ?
C6 C15 S1 . . 116.90(8) ?
S2 C15 S1 . . 117.97(6) ?
C17 C16 S1 . . 114.63(8) ?
C17 C16 H16A . . 108.6 ?
S1 C16 H16A . . 108.6 ?
C17 C16 H16B . . 108.6 ?
S1 C16 H16B . . 108.6 ?
H16A C16 H16B . . 107.6 ?
C16 C17 C18 . . 111.18(10) ?
C16 C17 H17A . . 109.4 ?
C18 C17 H17A . . 109.4 ?
C16 C17 H17B . . 109.4 ?
C18 C17 H17B . . 109.4 ?
H17A C17 H17B . . 108.0 ?
C19 C18 C17 . . 112.52(11) ?
C19 C18 H18A . . 109.1 ?
C17 C18 H18A . . 109.1 ?
C19 C18 H18B . . 109.1 ?
C17 C18 H18B . . 109.1 ?
H18A C18 H18B . . 107.8 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
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
Cl1 C10 . 1.7287(11) ?
Cl2 C12 . 1.7387(12) ?
S1 C15 . 1.7628(11) ?
S1 C16 . 1.8094(12) ?
S2 C15 . 1.6851(11) ?
O1 C1 . 1.2244(16) ?
N1 C5 . 1.3291(14) ?
N1 C9 . 1.4293(14) ?
N1 H1 . 0.911(18) ?
C1 C6 . 1.4733(15) ?
C1 C2 . 1.5061(16) ?
C2 C3 . 1.5214(15) ?
C2 H2A . 0.99 ?
C2 H2B . 0.99 ?
C3 C4 . 1.5258(15) ?
C3 C8 . 1.5300(16) ?
C3 C7 . 1.5307(16) ?
C4 C5 . 1.5063(15) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.4269(15) ?
C6 C15 . 1.4562(15) ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9 C14 . 1.3903(16) ?
C9 C10 . 1.3973(16) ?
C10 C11 . 1.3885(16) ?
C11 C12 . 1.3840(17) ?
C11 H11 . 0.95 ?
C12 C13 . 1.3856(17) ?
C13 C14 . 1.3916(16) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?
C16 C17 . 1.5222(16) ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C17 C18 . 1.5315(16) ?
C17 H17A . 0.99 ?
C17 H17B . 0.99 ?
C18 C19 . 1.5240(19) ?
C18 H18A . 0.99 ?
C18 H18B . 0.99 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
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
_geom_hbond_publ_flag
N1 H1 S2 . 0.91(2) 2.08(2) 2.8850(10) 147(2) yes
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
O1 C1 C2 C3 . . . . -149.43(13) ?
C6 C1 C2 C3 . . . . 31.47(16) ?
C1 C2 C3 C4 . . . . -52.05(13) ?
C1 C2 C3 C8 . . . . 68.46(13) ?
C1 C2 C3 C7 . . . . -170.06(10) ?
C2 C3 C4 C5 . . . . 52.18(12) ?
C8 C3 C4 C5 . . . . -68.83(13) ?
C7 C3 C4 C5 . . . . 170.62(9) ?
C9 N1 C5 C6 . . . . 175.52(10) ?
C9 N1 C5 C4 . . . . -7.29(16) ?
C3 C4 C5 N1 . . . . 151.63(10) ?
C3 C4 C5 C6 . . . . -31.13(15) ?
N1 C5 C6 C15 . . . . 2.50(17) ?
C4 C5 C6 C15 . . . . -174.53(10) ?
N1 C5 C6 C1 . . . . -177.12(10) ?
C4 C5 C6 C1 . . . . 5.84(15) ?
O1 C1 C6 C5 . . . . 174.85(13) ?
C2 C1 C6 C5 . . . . -6.09(16) ?
O1 C1 C6 C15 . . . . -4.79(19) ?
C2 C1 C6 C15 . . . . 174.27(10) ?
C5 N1 C9 C14 . . . . 95.10(14) ?
C5 N1 C9 C10 . . . . -86.58(14) ?
C14 C9 C10 C11 . . . . -2.07(17) ?
N1 C9 C10 C11 . . . . 179.58(10) ?
C14 C9 C10 Cl1 . . . . 178.25(9) ?
N1 C9 C10 Cl1 . . . . -0.10(15) ?
C9 C10 C11 C12 . . . . 0.65(17) ?
Cl1 C10 C11 C12 . . . . -179.66(9) ?
C10 C11 C12 C13 . . . . 1.04(17) ?
C10 C11 C12 Cl2 . . . . -179.71(9) ?
C11 C12 C13 C14 . . . . -1.26(18) ?
Cl2 C12 C13 C14 . . . . 179.50(9) ?
C10 C9 C14 C13 . . . . 1.84(17) ?
N1 C9 C14 C13 . . . . -179.82(10) ?
C12 C13 C14 C9 . . . . -0.21(17) ?
C5 C6 C15 S2 . . . . -0.17(16) ?
C1 C6 C15 S2 . . . . 179.44(9) ?
C5 C6 C15 S1 . . . . 178.79(8) ?
C1 C6 C15 S1 . . . . -1.60(14) ?
C16 S1 C15 C6 . . . . -175.86(8) ?
C16 S1 C15 S2 . . . . 3.18(8) ?
C15 S1 C16 C17 . . . . -89.34(9) ?
S1 C16 C17 C18 . . . . -170.96(8) ?
C16 C17 C18 C19 . . . . -174.62(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743284
