#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/75/2017548.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_2017548
loop_
_publ_author_name
'Insuasty, Henry'
'Castro, Edison'
'Sánchez, Edison'
'Cobo, Justo'
'Glidewell, Christopher'
_publ_section_title
;
 Hydrogen-bonding patterns in two aroylthiocarbamates and two
 aroylimidothiocarbonates
;
_journal_coeditor_code           FA3214
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o141
_journal_page_last               o146
_journal_paper_doi               10.1107/S0108270110005032
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H17 N O2 S'
_chemical_formula_moiety         'C13 H17 N O2 S'
_chemical_formula_sum            'C13 H17 N O2 S'
_chemical_formula_weight         251.35
_chemical_name_systematic
;
O,S-diethyl (4-methylbenzoyl)imidothiocarbonate
;
_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
_cell_angle_alpha                100.691(7)
_cell_angle_beta                 99.984(13)
_cell_angle_gamma                107.307(11)
_cell_formula_units_Z            2
_cell_length_a                   7.2470(16)
_cell_length_b                   8.8870(7)
_cell_length_c                   10.7370(10)
_cell_measurement_reflns_used    2460
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      3.20
_cell_volume                     629.19(17)
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg et al.,  2000)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EVALCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2460
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2460
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0597
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0398P)²+1.4311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1610
_refine_ls_wR_factor_ref         0.1671
_reflns_number_gt                2064
_reflns_number_total             2460
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3214.cif
_cod_data_source_block           III
_cod_database_code               2017548
_cod_database_fobs_code          2017548
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
C C1 0.2399(5) 0.3732(4) 0.3110(3) 0.0209(8) Uani d . 1 . .
O O1 0.2428(4) 0.4849(3) 0.2609(2) 0.0273(6) Uani d . 1 . .
N N2 0.2465(4) 0.3780(4) 0.4408(3) 0.0209(6) Uani d . 1 . .
C C3 0.2579(5) 0.5096(4) 0.5199(3) 0.0192(7) Uani d . 1 . .
S S31 0.26244(14) 0.69351(11) 0.48636(9) 0.0220(3) Uani d . 1 . .
C C32 0.2713(6) 0.8125(4) 0.6447(3) 0.0233(8) Uani d . 1 . .
H H32A 0.1534 0.7594 0.6756 0.028 Uiso calc R 1 . .
H H32B 0.3927 0.8227 0.7092 0.028 Uiso calc R 1 . .
C C33 0.2735(7) 0.9786(5) 0.6291(4) 0.0295(9) Uani d . 1 . .
H H33A 0.3915 1.0302 0.5993 0.044 Uiso calc R 1 . .
H H33B 0.2772 1.0464 0.7133 0.044 Uiso calc R 1 . .
H H33C 0.1531 0.9668 0.5646 0.044 Uiso calc R 1 . .
O O41 0.2677(4) 0.5126(3) 0.6444(2) 0.0214(6) Uani d . 1 . .
C C42 0.2605(6) 0.3634(4) 0.6821(3) 0.0232(8) Uani d . 1 . .
H H42A 0.3754 0.3314 0.6652 0.028 Uiso calc R 1 . .
H H42B 0.1361 0.2741 0.6320 0.028 Uiso calc R 1 . .
C C43 0.2679(8) 0.3969(5) 0.8243(4) 0.0361(10) Uani d . 1 . .
H H43A 0.3918 0.4854 0.8725 0.054 Uiso calc R 1 . .
H H43B 0.2630 0.2986 0.8545 0.054 Uiso calc R 1 . .
H H43C 0.1537 0.4288 0.8395 0.054 Uiso calc R 1 . .
C C11 0.2342(5) 0.2128(4) 0.2367(3) 0.0213(7) Uani d . 1 . .
C C12 0.2106(5) 0.0801(4) 0.2895(3) 0.0237(8) Uani d . 1 . .
H H12 0.1963 0.0905 0.3767 0.028 Uiso calc R 1 . .
C C13 0.2074(6) -0.0675(4) 0.2185(4) 0.0250(8) Uani d . 1 . .
H H13 0.1892 -0.1575 0.2566 0.030 Uiso calc R 1 . .
C C14 0.2305(6) -0.0847(4) 0.0919(4) 0.0251(8) Uani d . 1 . .
C C15 0.2545(6) 0.0478(5) 0.0396(4) 0.0292(9) Uani d . 1 . .
H H15 0.2718 0.0379 -0.0469 0.035 Uiso calc R 1 . .
C C16 0.2542(6) 0.1947(5) 0.1091(3) 0.0249(8) Uani d . 1 . .
H H16 0.2676 0.2834 0.0697 0.030 Uiso calc R 1 . .
C C17 0.2257(7) -0.2452(5) 0.0150(4) 0.0344(10) Uani d . 1 . .
H H17A 0.0910 -0.3060 -0.0399 0.052 Uiso calc R 1 . .
H H17B 0.2629 -0.3079 0.0750 0.052 Uiso calc R 1 . .
H H17C 0.3201 -0.2268 -0.0405 0.052 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
O1 C1 N2 . . 125.7(3) ?
O1 C1 C11 . . 122.4(3) ?
N2 C1 C11 . . 111.9(3) ?
C3 N2 C1 . . 120.0(3) ?
N2 C3 O41 . . 119.1(3) ?
N2 C3 S31 . . 128.3(3) ?
O41 C3 S31 . . 112.6(2) ?
C3 S31 C32 . . 101.54(16) ?
C33 C32 S31 . . 107.2(2) ?
C33 C32 H32A . . 110.3 ?
S31 C32 H32A . . 110.3 ?
C33 C32 H32B . . 110.3 ?
S31 C32 H32B . . 110.3 ?
H32A C32 H32B . . 108.5 ?
C32 C33 H33A . . 109.5 ?
C32 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
C32 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C3 O41 C42 . . 116.9(3) ?
O41 C42 C43 . . 106.4(3) ?
O41 C42 H42A . . 110.4 ?
C43 C42 H42A . . 110.4 ?
O41 C42 H42B . . 110.4 ?
C43 C42 H42B . . 110.4 ?
H42A C42 H42B . . 108.6 ?
C42 C43 H43A . . 109.5 ?
C42 C43 H43B . . 109.5 ?
H43A C43 H43B . . 109.5 ?
C42 C43 H43C . . 109.5 ?
H43A C43 H43C . . 109.5 ?
H43B C43 H43C . . 109.5 ?
C12 C11 C16 . . 118.3(3) ?
C12 C11 C1 . . 122.6(3) ?
C16 C11 C1 . . 119.1(3) ?
C11 C12 C13 . . 121.4(3) ?
C11 C12 H12 . . 119.3 ?
C13 C12 H12 . . 119.3 ?
C12 C13 C14 . . 120.2(4) ?
C12 C13 H13 . . 119.9 ?
C14 C13 H13 . . 119.9 ?
C15 C14 C13 . . 118.2(3) ?
C15 C14 C17 . . 121.7(3) ?
C13 C14 C17 . . 120.0(4) ?
C14 C15 C16 . . 121.8(3) ?
C14 C15 H15 . . 119.1 ?
C16 C15 H15 . . 119.1 ?
C15 C16 C11 . . 119.9(4) ?
C15 C16 H16 . . 120.0 ?
C11 C16 H16 . . 120.0 ?
C14 C17 H17A . . 109.5 ?
C14 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C14 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 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
C1 O1 . 1.210(4) ?
C1 N2 . 1.379(4) ?
C1 C11 . 1.484(5) ?
N2 C3 . 1.283(4) ?
C3 O41 . 1.321(4) ?
C3 S31 . 1.730(4) ?
S31 C32 . 1.807(4) ?
C32 C33 . 1.512(5) ?
C32 H32A . 0.9900 ?
C32 H32B . 0.9900 ?
C33 H33A . 0.9800 ?
C33 H33B . 0.9800 ?
C33 H33C . 0.9800 ?
O41 C42 . 1.445(4) ?
C42 C43 . 1.489(5) ?
C42 H42A . 0.9900 ?
C42 H42B . 0.9900 ?
C43 H43A . 0.9800 ?
C43 H43B . 0.9800 ?
C43 H43C . 0.9800 ?
C11 C12 . 1.380(5) ?
C11 C16 . 1.386(5) ?
C12 C13 . 1.381(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.384(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.375(5) ?
C14 C17 . 1.497(5) ?
C15 C16 . 1.380(5) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 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
_geom_hbond_publ_flag
C32 H32B Cg1 2_666 0.99 2.62 3.554(5) 158 no
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 N2 C3 . . . . -0.4(6) ?
C11 C1 N2 C3 . . . . 177.9(3) ?
C1 N2 C3 O41 . . . . -178.8(3) ?
C1 N2 C3 S31 . . . . 1.3(5) ?
N2 C3 S31 C32 . . . . 178.1(3) ?
O41 C3 S31 C32 . . . . -1.8(3) ?
C3 S31 C32 C33 . . . . -179.4(3) ?
N2 C3 O41 C42 . . . . -1.3(5) ?
S31 C3 O41 C42 . . . . 178.7(3) ?
C3 O41 C42 C43 . . . . -178.4(3) ?
O1 C1 C11 C12 . . . . -173.3(4) ?
N2 C1 C11 C12 . . . . 8.3(5) ?
O1 C1 C11 C16 . . . . 7.0(5) ?
N2 C1 C11 C16 . . . . -171.4(3) ?
C16 C11 C12 C13 . . . . 0.2(5) ?
C1 C11 C12 C13 . . . . -179.5(3) ?
C11 C12 C13 C14 . . . . 0.8(6) ?
C12 C13 C14 C15 . . . . -0.6(6) ?
C12 C13 C14 C17 . . . . -179.6(4) ?
C13 C14 C15 C16 . . . . -0.6(6) ?
C17 C14 C15 C16 . . . . 178.4(4) ?
C14 C15 C16 C11 . . . . 1.6(6) ?
C12 C11 C16 C15 . . . . -1.4(6) ?
C1 C11 C16 C15 . . . . 178.3(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654217
