#------------------------------------------------------------------------------
#$Date: 2017-04-05 12:12:26 +0300 (Wed, 05 Apr 2017) $
#$Revision: 194948 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/97/7119797.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7119797
loop_
_publ_author_name
'Noor, Asif'
'Li, Jiawei'
'Khairallah, George N.'
'Li, Zhen'
'Ghari, Hossein'
'Canty, Allan J.'
'Ariafard, Alireza'
'Donnelly, Paul S.'
'O'Hair, Richard A J'
_publ_section_title
;
 A one-pot route to thioamides discovered by gas-phase studies:
 palladium-mediated CO2 extrusion followed by insertion of
 isothiocyanates.
;
_journal_issue                   27
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3854
_journal_page_last               3857
_journal_paper_doi               10.1039/c7cc00865a
_journal_volume                  53
_journal_year                    2017
_chemical_formula_sum            'C10 H13 N O2 S'
_chemical_formula_weight         211.27
_chemical_name_systematic        2,6-dimethoxy-N-methylbenzothioamide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-03-16 deposited with the CCDC.
2017-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.1567(2)
_cell_length_b                   8.34180(10)
_cell_length_c                   8.61660(10)
_cell_measurement_reflns_used    7167
_cell_measurement_temperature    130.00(10)
_cell_measurement_theta_max      76.9920
_cell_measurement_theta_min      6.0520
_cell_volume                     1089.43(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      130.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8872
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.001
_diffrn_reflns_theta_min         6.055
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.445
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       Block
_exptl_crystal_F_000             448
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.723
_exptl_crystal_size_mid          0.431
_exptl_crystal_size_min          0.358
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 983 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2220
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0251
_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)+(0.0523P)²+0.0311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0659
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                2209
_reflns_number_total             2220
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cc00865a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7119797--7119802.cif.'
_cod_database_code               7119797
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_solvent_exptl_crystal_recrystallization_method
'Slow evaporation of dichloromethane and pentane mixtures'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
S1 S 0.61332(2) 0.60397(4) 0.74235(5) 0.02069(14) Uani 1 1 d
O1 O 0.62871(8) 0.80037(18) 0.37974(18) 0.0303(3) Uani 1 1 d
O2 O 0.38594(7) 0.59223(16) 0.63869(19) 0.0264(3) Uani 1 1 d
N1 N 0.56450(10) 0.44574(17) 0.48899(18) 0.0226(3) Uani 1 1 d
C8 C 0.50402(10) 0.70560(17) 0.50652(18) 0.0178(3) Uani 1 1 d
C6 C 0.41379(11) 0.70968(19) 0.54018(19) 0.0199(3) Uani 1 1 d
C5 C 0.35997(11) 0.8278(2) 0.4758(2) 0.0249(4) Uani 1 1 d
C2 C 0.54062(11) 0.81869(19) 0.4069(2) 0.0221(3) Uani 1 1 d
C9 C 0.56075(10) 0.57642(18) 0.57371(19) 0.0163(3) Uani 1 1 d
C3 C 0.48781(13) 0.9393(2) 0.3429(2) 0.0289(4) Uani 1 1 d
C4 C 0.39898(13) 0.9420(2) 0.3792(3) 0.0286(4) Uani 1 1 d
C7 C 0.29365(13) 0.5652(3) 0.6516(3) 0.0386(5) Uani 1 1 d
C1 C 0.66620(15) 0.8927(3) 0.2573(3) 0.0402(5) Uani 1 1 d
C10 C 0.61475(15) 0.3035(3) 0.5304(3) 0.0347(5) Uani 1 1 d
H4 H 0.5135(17) 1.022(3) 0.273(3) 0.037(6) Uiso 1 1 d
H1 H 0.731(2) 0.854(4) 0.259(4) 0.049(7) Uiso 1 1 d
H6 H 0.3013(16) 0.838(3) 0.489(3) 0.025(6) Uiso 1 1 d
H5 H 0.3626(19) 1.029(3) 0.334(3) 0.037(7) Uiso 1 1 d
H9 H 0.2886(17) 0.468(3) 0.712(4) 0.034(6) Uiso 1 1 d
H10 H 0.532(2) 0.438(4) 0.403(4) 0.050(8) Uiso 1 1 d
H3 H 0.642(2) 0.862(4) 0.163(4) 0.045(8) Uiso 1 1 d
H2 H 0.662(2) 1.013(4) 0.275(4) 0.057(9) Uiso 1 1 d
H7 H 0.257(3) 0.664(4) 0.693(5) 0.074(11) Uiso 1 1 d
H13 H 0.607(2) 0.278(4) 0.638(5) 0.052(9) Uiso 1 1 d
H8 H 0.270(2) 0.544(4) 0.549(5) 0.062(9) Uiso 1 1 d
H11 H 0.672(2) 0.320(4) 0.504(5) 0.065(10) Uiso 1 1 d
H12 H 0.590(2) 0.210(5) 0.492(5) 0.067(11) Uiso 1 1 d
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'
O O 0.0492 0.0322 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 C1 117.18(15)
C6 O2 C7 117.87(15)
C9 N1 C10 124.30(16)
C9 N1 H10 119.7(19)
C10 N1 H10 115.9(19)
C2 C8 C6 120.10(15)
C2 C8 C9 119.90(14)
C6 C8 C9 119.97(14)
O2 C6 C5 125.06(15)
O2 C6 C8 114.49(14)
C5 C6 C8 120.45(16)
C6 C5 C4 118.13(17)
C6 C5 H6 126.4(15)
C4 C5 H6 115.4(15)
O1 C2 C8 114.84(14)
O1 C2 C3 124.98(16)
C8 C2 C3 120.18(16)
N1 C9 C8 114.07(14)
N1 C9 S1 125.19(12)
C8 C9 S1 120.74(12)
C4 C3 C2 118.67(17)
C4 C3 H4 120.4(16)
C2 C3 H4 120.9(16)
C3 C4 C5 122.43(16)
C3 C4 H5 117.8(17)
C5 C4 H5 119.8(17)
O2 C7 H9 104.7(15)
O2 C7 H7 115(2)
H9 C7 H7 116(3)
O2 C7 H8 109(2)
H9 C7 H8 108(3)
H7 C7 H8 104(3)
O1 C1 H1 101.6(18)
O1 C1 H3 110(2)
H1 C1 H3 107(3)
O1 C1 H2 113(2)
H1 C1 H2 112(2)
H3 C1 H2 112(3)
N1 C10 H13 111(2)
N1 C10 H11 109(2)
H13 C10 H11 113(3)
N1 C10 H12 113(2)
H13 C10 H12 96(3)
H11 C10 H12 115(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C9 1.6731(17)
O1 C2 1.364(2)
O1 C1 1.424(3)
O2 C6 1.363(2)
O2 C7 1.421(2)
N1 C9 1.313(2)
N1 C10 1.454(2)
N1 H10 0.90(4)
C8 C2 1.391(2)
C8 C6 1.398(2)
C8 C9 1.495(2)
C6 C5 1.394(2)
C5 C4 1.396(3)
C5 H6 0.90(2)
C2 C3 1.399(2)
C3 C4 1.382(3)
C3 H4 0.99(3)
C4 H5 0.99(3)
C7 H9 0.96(3)
C7 H7 1.05(4)
C7 H8 0.97(4)
C1 H1 1.03(3)
C1 H3 0.93(4)
C1 H2 1.02(3)
C10 H13 0.95(4)
C10 H11 0.91(4)
C10 H12 0.93(4)
