#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224837.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_2224837
loop_
_publ_author_name
'Saeed, Aamer'
'Abbas, Naeem'
'Rafique, Hummera'
'Bolte, Michael'
_publ_section_title
;
 3,3'-Dibutanoyl-1,1'-(o-phenylene)dithiourea
;
_journal_coeditor_code           BG2318
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o441
_journal_paper_doi               10.1107/S1600536810001789
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C16 H22 N4 O2 S2'
_chemical_formula_moiety         'C16 H22 N4 O2 S2'
_chemical_formula_sum            'C16 H22 N4 O2 S2'
_chemical_formula_weight         366.50
_chemical_name_systematic
;
3,3'-Dibutanoyl-1,1'-(o-phenylene)dithiourea
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 91.949(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8099(5)
_cell_length_b                   16.4925(7)
_cell_length_c                   12.3923(8)
_cell_measurement_reflns_used    20465
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      3.4
_cell_volume                     1799.53(17)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Stoe IPDS II two-circle diffractometer'
_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  0.0866
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            22483
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.61
_diffrn_reflns_theta_min         3.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  0.9316
_exptl_absorpt_correction_T_min  0.9176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 2009; Blessing, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.332
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0360
_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)+(0.0595P)²+0.1390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                2890
_reflns_number_total             3360
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2318.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.

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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224837
_cod_database_fobs_code          2224837
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.07444(5) 0.68569(3) 0.35994(3) 0.02446(14) Uani d . 1 . .
S S2 0.47542(5) 0.79179(3) 0.52094(3) 0.02947(14) Uani d . 1 . .
O O1 0.38901(14) 0.53284(9) 0.57778(9) 0.0278(3) Uani d . 1 . .
O O2 0.83408(13) 0.59749(8) 0.58037(9) 0.0224(3) Uani d . 1 . .
C C1 0.42857(18) 0.65251(9) 0.31239(12) 0.0152(3) Uani d . 1 . .
C C2 0.57714(18) 0.67920(9) 0.33537(12) 0.0154(3) Uani d . 1 . .
C C3 0.66576(19) 0.70843(10) 0.25383(13) 0.0206(3) Uani d . 1 . .
H H3 0.7674 0.7249 0.2695 0.025 Uiso calc R 1 . .
C C4 0.6054(2) 0.71355(11) 0.14871(13) 0.0228(4) Uani d . 1 . .
H H4 0.6654 0.7342 0.0927 0.027 Uiso calc R 1 . .
C C5 0.4579(2) 0.68847(10) 0.12589(12) 0.0211(4) Uani d . 1 . .
H H5 0.4170 0.6924 0.0542 0.025 Uiso calc R 1 . .
C C6 0.36860(19) 0.65746(10) 0.20698(12) 0.0180(3) Uani d . 1 . .
H H6 0.2678 0.6399 0.1906 0.022 Uiso calc R 1 . .
N N11 0.34909(15) 0.61572(8) 0.39740(10) 0.0160(3) Uani d . 1 . .
H H11 0.401(2) 0.5867(12) 0.4430(16) 0.019 Uiso d . 1 . .
C C11 0.20588(17) 0.62849(10) 0.42462(12) 0.0159(3) Uani d . 1 . .
N N12 0.16371(16) 0.58921(8) 0.51872(10) 0.0168(3) Uani d . 1 . .
H H12 0.072(2) 0.5945(12) 0.5357(15) 0.020 Uiso d . 1 . .
C C12 0.25388(19) 0.54519(10) 0.59085(12) 0.0195(3) Uani d . 1 . .
C C13 0.1723(2) 0.51260(12) 0.68687(14) 0.0272(4) Uani d . 1 . .
H H13A 0.1316 0.4581 0.6691 0.033 Uiso calc R 1 . .
H H13B 0.0852 0.5484 0.7017 0.033 Uiso calc R 1 . .
C C14 0.2751(2) 0.50692(12) 0.78795(14) 0.0285(4) Uani d . 1 . .
H H14A 0.2206 0.4776 0.8446 0.034 Uiso calc R 1 . .
H H14B 0.3663 0.4748 0.7711 0.034 Uiso calc R 1 . .
C C15 0.3251(3) 0.58888(14) 0.83166(17) 0.0447(5) Uani d . 1 . .
H H15A 0.3912 0.5812 0.8961 0.054 Uiso calc R 1 . .
H H15B 0.2357 0.6205 0.8506 0.054 Uiso calc R 1 . .
H H15C 0.3809 0.6179 0.7765 0.054 Uiso calc R 1 . .
N N21 0.64067(16) 0.67101(9) 0.44277(10) 0.0170(3) Uani d . 1 . .
H H21 0.708(2) 0.6374(13) 0.4558(15) 0.020 Uiso d . 1 . .
C C21 0.59630(17) 0.71486(10) 0.52676(12) 0.0171(3) Uani d . 1 . .
N N22 0.65944(15) 0.69253(8) 0.62711(11) 0.0172(3) Uani d . 1 . .
H H22 0.630(2) 0.7231(13) 0.6794(16) 0.021 Uiso d . 1 . .
C C22 0.77077(18) 0.63670(10) 0.65070(12) 0.0178(3) Uani d . 1 . .
C C23 0.8064(2) 0.62499(11) 0.76915(12) 0.0223(4) Uani d . 1 . .
H H23A 0.7462 0.6636 0.8114 0.027 Uiso calc R 1 . .
H H23B 0.9154 0.6361 0.7847 0.027 Uiso calc R 1 . .
C C24 0.7692(2) 0.53829(12) 0.80244(14) 0.0308(4) Uani d . 1 . .
H H24A 0.6617 0.5264 0.7825 0.037 Uiso calc R 1 . .
H H24B 0.8335 0.5000 0.7627 0.037 Uiso calc R 1 . .
C C25 0.7954(4) 0.52563(15) 0.92284(17) 0.0580(8) Uani d . 1 . .
H H25A 0.7694 0.4697 0.9415 0.070 Uiso calc R 1 . .
H H25B 0.7314 0.5632 0.9623 0.070 Uiso calc R 1 . .
H H25C 0.9024 0.5358 0.9424 0.070 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'
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
C6 C1 C2 . . 119.57(14) ?
C6 C1 N11 . . 122.61(14) ?
C2 C1 N11 . . 117.65(13) ?
C3 C2 C1 . . 120.47(14) ?
C3 C2 N21 . . 119.91(14) ?
C1 C2 N21 . . 119.48(14) ?
C2 C3 C4 . . 119.80(15) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C5 C4 C3 . . 119.94(15) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.74(15) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C1 . . 119.45(15) ?
C5 C6 H6 . . 120.3 ?
C1 C6 H6 . . 120.3 ?
C11 N11 C1 . . 127.91(14) ?
C11 N11 H11 . . 114.1(12) ?
C1 N11 H11 . . 117.4(13) ?
N11 C11 N12 . . 114.78(14) ?
N11 C11 S1 . . 127.73(12) ?
N12 C11 S1 . . 117.49(11) ?
C12 N12 C11 . . 128.39(14) ?
C12 N12 H12 . . 115.2(13) ?
C11 N12 H12 . . 116.3(13) ?
O1 C12 N12 . . 122.84(14) ?
O1 C12 C13 . . 122.44(15) ?
N12 C12 C13 . . 114.71(14) ?
C12 C13 C14 . . 112.57(15) ?
C12 C13 H13A . . 109.1 ?
C14 C13 H13A . . 109.1 ?
C12 C13 H13B . . 109.1 ?
C14 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.8 ?
C15 C14 C13 . . 113.35(16) ?
C15 C14 H14A . . 108.9 ?
C13 C14 H14A . . 108.9 ?
C15 C14 H14B . . 108.9 ?
C13 C14 H14B . . 108.9 ?
H14A C14 H14B . . 107.7 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C21 N21 C2 . . 123.85(14) ?
C21 N21 H21 . . 116.0(13) ?
C2 N21 H21 . . 120.1(13) ?
N21 C21 N22 . . 115.68(14) ?
N21 C21 S2 . . 125.81(12) ?
N22 C21 S2 . . 118.52(12) ?
C22 N22 C21 . . 128.97(14) ?
C22 N22 H22 . . 117.5(13) ?
C21 N22 H22 . . 113.1(13) ?
O2 C22 N22 . . 122.64(14) ?
O2 C22 C23 . . 122.56(15) ?
N22 C22 C23 . . 114.77(14) ?
C22 C23 C24 . . 110.15(14) ?
C22 C23 H23A . . 109.6 ?
C24 C23 H23A . . 109.6 ?
C22 C23 H23B . . 109.6 ?
C24 C23 H23B . . 109.6 ?
H23A C23 H23B . . 108.1 ?
C25 C24 C23 . . 111.58(16) ?
C25 C24 H24A . . 109.3 ?
C23 C24 H24A . . 109.3 ?
C25 C24 H24B . . 109.3 ?
C23 C24 H24B . . 109.3 ?
H24A C24 H24B . . 108.0 ?
C24 C25 H25A . . 109.5 ?
C24 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C24 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 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
S1 C11 . 1.6763(16) ?
S2 C21 . 1.6566(16) ?
O1 C12 . 1.224(2) ?
O2 C22 . 1.234(2) ?
C1 C6 . 1.395(2) ?
C1 C2 . 1.401(2) ?
C1 N11 . 1.4207(19) ?
C2 C3 . 1.385(2) ?
C2 N21 . 1.4325(19) ?
C3 C4 . 1.393(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.384(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.394(2) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
N11 C11 . 1.334(2) ?
N11 H11 . 0.86(2) ?
C11 N12 . 1.395(2) ?
N12 C12 . 1.382(2) ?
N12 H12 . 0.84(2) ?
C12 C13 . 1.510(2) ?
C13 C14 . 1.524(3) ?
C13 H13A . 0.9900 ?
C13 H13B . 0.9900 ?
C14 C15 . 1.516(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
N21 C21 . 1.337(2) ?
N21 H21 . 0.83(2) ?
C21 N22 . 1.395(2) ?
N22 C22 . 1.370(2) ?
N22 H22 . 0.87(2) ?
C22 C23 . 1.503(2) ?
C23 C24 . 1.527(3) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 C25 . 1.516(3) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
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
N11 H11 O1 . 0.86(2) 1.90(2) 2.6336(17) 142.6(17)
N12 H12 O2 1_455 0.84(2) 2.19(2) 3.0309(18) 175.3(19)
N21 H21 O2 . 0.83(2) 1.98(2) 2.6616(18) 139.1(18)
N22 H22 S1 4_676 0.87(2) 2.75(2) 3.6147(14) 172.0(17)
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
C6 C1 C2 C3 . . . . -1.7(2) ?
N11 C1 C2 C3 . . . . 173.81(15) ?
C6 C1 C2 N21 . . . . -177.47(14) ?
N11 C1 C2 N21 . . . . -2.0(2) ?
C1 C2 C3 C4 . . . . 1.9(2) ?
N21 C2 C3 C4 . . . . 177.67(15) ?
C2 C3 C4 C5 . . . . -0.8(3) ?
C3 C4 C5 C6 . . . . -0.4(3) ?
C4 C5 C6 C1 . . . . 0.6(2) ?
C2 C1 C6 C5 . . . . 0.4(2) ?
N11 C1 C6 C5 . . . . -174.83(15) ?
C6 C1 N11 C11 . . . . -49.1(2) ?
C2 C1 N11 C11 . . . . 135.57(16) ?
C1 N11 C11 N12 . . . . -174.00(14) ?
C1 N11 C11 S1 . . . . 5.6(2) ?
N11 C11 N12 C12 . . . . 6.0(2) ?
S1 C11 N12 C12 . . . . -173.65(13) ?
C11 N12 C12 O1 . . . . -2.4(3) ?
C11 N12 C12 C13 . . . . 178.22(16) ?
O1 C12 C13 C14 . . . . 31.9(2) ?
N12 C12 C13 C14 . . . . -148.67(15) ?
C12 C13 C14 C15 . . . . 67.2(2) ?
C3 C2 N21 C21 . . . . 113.70(18) ?
C1 C2 N21 C21 . . . . -70.5(2) ?
C2 N21 C21 N22 . . . . 173.38(14) ?
C2 N21 C21 S2 . . . . -6.7(2) ?
N21 C21 N22 C22 . . . . 6.5(2) ?
S2 C21 N22 C22 . . . . -173.42(13) ?
C21 N22 C22 O2 . . . . 1.0(3) ?
C21 N22 C22 C23 . . . . -177.18(15) ?
O2 C22 C23 C24 . . . . -61.4(2) ?
N22 C22 C23 C24 . . . . 116.77(17) ?
C22 C23 C24 C25 . . . . -176.8(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744315
