#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/93/2229365.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_2229365
loop_
_publ_author_name
'Selvakumaran, N.'
'Karvembu, R.'
'Ng, Seik Weng'
'Tiekink, Edward R. T.'
_publ_section_title
;
 1-Benzoyl-3,3-bis(2-methylpropyl)thiourea
;
_journal_coeditor_code           EZ2230
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o602
_journal_paper_doi               10.1107/S1600536811004557
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H24 N2 O S'
_chemical_formula_moiety         'C16 H24 N2 O S'
_chemical_formula_sum            'C16 H24 N2 O S'
_chemical_formula_weight         292.43
_chemical_name_systematic
;
1-Benzoyl-3,3-bis(2-methylpropyl)thiourea
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.776(9)
_cell_angle_beta                 112.734(10)
_cell_angle_gamma                100.782(9)
_cell_formula_units_Z            2
_cell_length_a                   8.9331(10)
_cell_length_b                   10.1023(9)
_cell_length_c                   11.0725(12)
_cell_measurement_reflns_used    1845
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.2
_cell_measurement_theta_min      2.2
_cell_volume                     837.47(19)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics
'ORTEP-3 (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      295(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type
;
Agilent Supernova Dual diffractometer with an Atlas detector
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_av_sigmaI/netI    0.052
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6265
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.2
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.86
_refine_diff_density_min         -0.58
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3693
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.08
_refine_ls_R_factor_all          0.122
_refine_ls_R_factor_gt           0.074
_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)+(0.078P)²+0.7593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.176
_refine_ls_wR_factor_ref         0.219
_reflns_number_gt                2232
_reflns_number_total             3693
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2230.cif
_cod_data_source_block           I
_cod_database_code               2229365
_cod_database_fobs_code          2229365
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.74828(14) 0.92803(11) 0.99096(12) 0.0711(4) Uani d . 1 . .
O O1 0.6998(3) 0.5295(2) 0.7153(3) 0.0585(7) Uani d . 1 . .
N N1 0.8690(3) 0.7638(3) 0.8494(3) 0.0512(7) Uani d . 1 . .
H H1 0.9753 0.8236 0.8909 0.061 Uiso calc R 1 . .
N N2 0.6172(3) 0.7981(3) 0.7098(3) 0.0515(7) Uani d . 1 . .
C C1 0.9961(4) 0.5699(3) 0.8524(3) 0.0431(7) Uani d . 1 . .
C C2 0.9697(5) 0.4222(4) 0.8112(4) 0.0535(9) Uani d . 1 . .
H H2 0.8597 0.3566 0.7487 0.064 Uiso calc R 1 . .
C C3 1.1045(5) 0.3706(4) 0.8615(5) 0.0653(11) Uani d . 1 . .
H H3 1.0847 0.2708 0.8335 0.078 Uiso calc R 1 . .
C C4 1.2664(5) 0.4656(5) 0.9522(5) 0.0669(11) Uani d . 1 . .
H H4 1.3568 0.4306 0.9866 0.080 Uiso calc R 1 . .
C C5 1.2961(5) 0.6133(5) 0.9929(5) 0.0661(11) Uani d . 1 . .
H H5 1.4069 0.6780 1.0542 0.079 Uiso calc R 1 . .
C C6 1.1618(4) 0.6657(4) 0.9431(4) 0.0538(9) Uani d . 1 . .
H H6 1.1826 0.7656 0.9705 0.065 Uiso calc R 1 . .
C C7 0.8421(4) 0.6165(3) 0.7986(3) 0.0426(7) Uani d . 1 . .
C C8 0.7372(4) 0.8250(3) 0.8392(4) 0.0513(9) Uani d . 1 . .
C C9 0.6351(4) 0.7432(3) 0.5811(4) 0.0526(9) Uani d D 1 . .
H H9A 0.5352 0.6588 0.5122 0.063 Uiso calc R 1 . .
H H9B 0.7353 0.7118 0.6035 0.063 Uiso calc R 1 . .
C C10 0.6535(5) 0.8564(4) 0.5150(4) 0.0654(11) Uani d D 1 . .
H H10 0.5463 0.8792 0.4831 0.079 Uiso calc R 1 . .
C C11 0.6790(7) 0.7906(5) 0.3856(4) 0.0892(15) Uani d D 1 . .
H H11A 0.5849 0.7025 0.3204 0.134 Uiso calc R 1 . .
H H11B 0.7847 0.7691 0.4149 0.134 Uiso calc R 1 . .
H H11C 0.6835 0.8587 0.3403 0.134 Uiso calc R 1 . .
C C12 0.7998(6) 0.9970(4) 0.6237(5) 0.0877(15) Uani d D 1 . .
H H12A 0.8091 1.0661 0.5801 0.132 Uiso calc R 1 . .
H H12B 0.9057 0.9765 0.6583 0.132 Uiso calc R 1 . .
H H12C 0.7765 1.0367 0.7012 0.132 Uiso calc R 1 . .
C C13 0.4659(4) 0.8426(4) 0.6909(5) 0.0662(11) Uani d D 1 . .
H H13A 0.4206 0.8536 0.6005 0.079 Uiso calc R 1 . .
H H13B 0.5025 0.9377 0.7640 0.079 Uiso calc R 1 . .
C C14 0.3240(5) 0.7441(4) 0.6949(7) 0.106(2) Uani d D 1 . .
H H14 0.3640 0.7625 0.7957 0.127 Uiso calc R 1 . .
C C15 0.1645(5) 0.7914(5) 0.6518(6) 0.0888(15) Uani d D 1 . .
H H15A 0.1979 0.8950 0.6987 0.133 Uiso calc R 1 . .
H H15B 0.0863 0.7435 0.6785 0.133 Uiso calc R 1 . .
H H15C 0.1094 0.7655 0.5512 0.133 Uiso calc R 1 . .
C C16 0.2816(6) 0.5830(4) 0.6261(6) 0.0816(13) Uani d D 1 . .
H H16A 0.3853 0.5586 0.6554 0.122 Uiso calc R 1 . .
H H16B 0.2264 0.5542 0.5251 0.122 Uiso calc R 1 . .
H H16C 0.2058 0.5330 0.6536 0.122 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
C7 N1 C8 . . 124.2(3) ?
C7 N1 H1 . . 117.9 ?
C8 N1 H1 . . 117.9 ?
C8 N2 C13 . . 120.0(3) ?
C8 N2 C9 . . 124.2(3) ?
C13 N2 C9 . . 115.2(3) ?
C2 C1 C6 . . 118.6(3) ?
C2 C1 C7 . . 117.4(3) ?
C6 C1 C7 . . 124.0(3) ?
C1 C2 C3 . . 120.9(4) ?
C1 C2 H2 . . 119.6 ?
C3 C2 H2 . . 119.6 ?
C4 C3 C2 . . 120.1(4) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 120.0(3) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C4 C5 C6 . . 120.2(4) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C5 C6 C1 . . 120.2(3) ?
C5 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
O1 C7 N1 . . 121.4(3) ?
O1 C7 C1 . . 122.1(3) ?
N1 C7 C1 . . 116.6(3) ?
N2 C8 N1 . . 117.1(3) ?
N2 C8 S1 . . 125.9(3) ?
N1 C8 S1 . . 117.1(3) ?
N2 C9 C10 . . 113.3(3) ?
N2 C9 H9A . . 108.9 ?
C10 C9 H9A . . 108.9 ?
N2 C9 H9B . . 108.9 ?
C10 C9 H9B . . 108.9 ?
H9A C9 H9B . . 107.7 ?
C12 C10 C11 . . 112.2(3) ?
C12 C10 C9 . . 110.9(3) ?
C11 C10 C9 . . 109.1(3) ?
C12 C10 H10 . . 108.2 ?
C11 C10 H10 . . 108.2 ?
C9 C10 H10 . . 108.2 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C10 C12 H12A . . 109.5 ?
C10 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C10 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N2 C13 C14 . . 116.6(3) ?
N2 C13 H13A . . 108.1 ?
C14 C13 H13A . . 108.1 ?
N2 C13 H13B . . 108.1 ?
C14 C13 H13B . . 108.1 ?
H13A C13 H13B . . 107.3 ?
C13 C14 C16 . . 118.4(4) ?
C13 C14 C15 . . 111.0(3) ?
C16 C14 C15 . . 112.5(4) ?
C13 C14 H14 . . 104.5 ?
C16 C14 H14 . . 104.5 ?
C15 C14 H14 . . 104.5 ?
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 ?
C14 C16 H16A . . 109.5 ?
C14 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C14 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 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 C8 . 1.673(4) ?
O1 C7 . 1.214(4) ?
N1 C7 . 1.377(4) ?
N1 C8 . 1.410(4) ?
N1 H1 . 0.8800 ?
N2 C8 . 1.330(4) ?
N2 C13 . 1.461(4) ?
N2 C9 . 1.464(5) ?
C1 C2 . 1.380(5) ?
C1 C6 . 1.386(5) ?
C1 C7 . 1.493(4) ?
C2 C3 . 1.381(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.362(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.376(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.382(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C9 C10 . 1.533(4) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C12 . 1.528(4) ?
C10 C11 . 1.529(4) ?
C10 H10 . 0.9800 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.482(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C16 . 1.498(4) ?
C14 C15 . 1.530(4) ?
C14 H14 . 0.9800 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
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
N1 H1 S1 2_777 0.88 2.74 3.586(3) 162
C9 H9a O1 2_666 0.97 2.49 3.424(5) 162
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 . . . . 1.4(5) ?
C7 C1 C2 C3 . . . . -177.1(3) ?
C1 C2 C3 C4 . . . . -0.5(6) ?
C2 C3 C4 C5 . . . . -0.5(6) ?
C3 C4 C5 C6 . . . . 0.6(7) ?
C4 C5 C6 C1 . . . . 0.4(6) ?
C2 C1 C6 C5 . . . . -1.4(5) ?
C7 C1 C6 C5 . . . . 177.1(3) ?
C8 N1 C7 O1 . . . . 15.7(5) ?
C8 N1 C7 C1 . . . . -163.6(3) ?
C2 C1 C7 O1 . . . . -4.2(5) ?
C6 C1 C7 O1 . . . . 177.4(3) ?
C2 C1 C7 N1 . . . . 175.2(3) ?
C6 C1 C7 N1 . . . . -3.3(5) ?
C13 N2 C8 N1 . . . . 172.5(3) ?
C9 N2 C8 N1 . . . . -16.3(5) ?
C13 N2 C8 S1 . . . . -9.0(5) ?
C9 N2 C8 S1 . . . . 162.2(3) ?
C7 N1 C8 N2 . . . . -61.8(5) ?
C7 N1 C8 S1 . . . . 119.6(3) ?
C8 N2 C9 C10 . . . . -109.9(4) ?
C13 N2 C9 C10 . . . . 61.7(4) ?
N2 C9 C10 C12 . . . . 53.6(4) ?
N2 C9 C10 C11 . . . . 177.6(3) ?
C8 N2 C13 C14 . . . . -82.1(5) ?
C9 N2 C13 C14 . . . . 105.9(4) ?
N2 C13 C14 C16 . . . . -39.2(7) ?
N2 C13 C14 C15 . . . . -171.4(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 3353558
