#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:01:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180284 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/70/7117067.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_7117067
loop_
_publ_author_name
'Xiaohan Ye'
'Jeffrey L. Petersen'
'Xiaodong Shi'
_publ_section_title
;
 Nickel-catalyzed directed sulfenylation of sp2 and sp3 C-H bonds
;
_journal_name_full               Chem.Commun.
_journal_page_first              7863
_journal_paper_doi               10.1039/C5cc01970B
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C22 H15 Cl N2 O S'
_chemical_formula_weight         390.87
_chemical_name_systematic
3-chloro-2-(phenylthio)-N-(quinolin-8-yl)benzamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2015-03-05 deposited with the CCDC.
2015-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.3945(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0459(5)
_cell_length_b                   10.3781(5)
_cell_length_c                   15.4051(7)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    293.(2)
_cell_measurement_theta_max      32.5824
_cell_measurement_theta_min      3.2223
_cell_volume                     1837.78(14)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker AXS D8 Venture fixed-chi'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  Triumph
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28740
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.77
_diffrn_source_type              fine-focus
_exptl_absorpt_coefficient_mu    0.336
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/3 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method 'Vapour Deposition'
_exptl_crystal_size_max          0.660
_exptl_crystal_size_mid          0.607
_exptl_crystal_size_min          0.526
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.380
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0560
_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)+(0.0835P)²+1.1019P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1676
_reflns_number_gt                3444
_reflns_number_total             4214
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc01970b2.cif
_cod_data_source_block           Ia
_cod_database_code               7117067
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.33168(7) 0.52839(8) 0.11672(5) 0.0787(3) Uani d . . . 1 . .
S S1 0.59522(5) 0.48751(6) 0.23561(4) 0.0533(2) Uani d . . . 1 . .
O O1 0.67933(18) 0.13640(19) 0.32607(14) 0.0748(6) Uani d . . . 1 . .
N N1 0.69058(17) 0.31069(19) 0.41662(13) 0.0507(4) Uani d . . . 1 . .
H H1 0.6483 0.3698 0.4299 0.061 Uiso calc U . R 1 . .
N N2 0.75732(17) 0.49700(18) 0.53759(13) 0.0505(4) Uani d . . . 1 . .
C C1 0.6362(2) 0.2325(2) 0.34750(15) 0.0478(5) Uani d . . . 1 . .
C C2 0.51317(19) 0.2684(2) 0.29605(14) 0.0453(5) Uani d . . . 1 . .
C C3 0.4261(2) 0.1793(3) 0.29601(17) 0.0580(6) Uani d . . . 1 . .
H H3 0.444 0.105 0.3312 0.07 Uiso calc U . R 1 . .
C C4 0.3126(2) 0.2025(3) 0.24305(19) 0.0681(8) Uani d . . . 1 . .
H H4 0.2546 0.1439 0.2439 0.082 Uiso calc U . R 1 . .
C C5 0.2845(2) 0.3098(3) 0.18969(18) 0.0647(7) Uani d . . . 1 . .
H H5 0.2081 0.3241 0.1545 0.078 Uiso calc U . R 1 . .
C C6 0.3705(2) 0.3964(2) 0.18859(16) 0.0540(5) Uani d . . . 1 . .
C C7 0.48536(19) 0.3786(2) 0.24198(14) 0.0450(5) Uani d . . . 1 . .
C C8 0.58105(18) 0.6120(2) 0.31105(15) 0.0451(5) Uani d . . . 1 . .
C C9 0.6468(2) 0.7222(2) 0.31205(18) 0.0560(6) Uani d . . . 1 . .
H H9 0.6924 0.7288 0.2731 0.067 Uiso calc U . R 1 . .
C C10 0.6445(2) 0.8216(3) 0.3706(2) 0.0700(8) Uani d . . . 1 . .
H H10 0.6888 0.8951 0.3712 0.084 Uiso calc U . R 1 . .
C C11 0.5769(3) 0.8130(3) 0.4284(2) 0.0752(9) Uani d . . . 1 . .
H H11 0.576 0.88 0.4682 0.09 Uiso calc U . R 1 . .
C C12 0.5109(2) 0.7043(3) 0.42684(19) 0.0657(7) Uani d . . . 1 . .
H H12 0.4649 0.6985 0.4656 0.079 Uiso calc U . R 1 . .
C C13 0.5122(2) 0.6038(2) 0.36840(17) 0.0538(5) Uani d . . . 1 . .
H H13 0.467 0.5309 0.3676 0.065 Uiso calc U . R 1 . .
C C14 0.80788(19) 0.3082(2) 0.47011(14) 0.0454(5) Uani d . . . 1 . .
C C15 0.8889(2) 0.2174(3) 0.46488(16) 0.0582(6) Uani d . . . 1 . .
H H15 0.8674 0.1483 0.4249 0.07 Uiso calc U . R 1 . .
C C16 1.0041(2) 0.2301(3) 0.52041(18) 0.0683(8) Uani d . . . 1 . .
H H16 1.0584 0.1683 0.5165 0.082 Uiso calc U . R 1 . .
C C17 1.0392(2) 0.3291(3) 0.57955(16) 0.0618(7) Uani d . . . 1 . .
H H17 1.1165 0.3351 0.6149 0.074 Uiso calc U . R 1 . .
C C18 0.95850(19) 0.4227(2) 0.58741(14) 0.0489(5) Uani d . . . 1 . .
C C19 0.9862(2) 0.5283(3) 0.64795(17) 0.0587(6) Uani d . . . 1 . .
H H19 1.0621 0.5397 0.6851 0.07 Uiso calc U . R 1 . .
C C20 0.9026(2) 0.6126(3) 0.65187(18) 0.0639(7) Uani d . . . 1 . .
H H20 0.9201 0.6823 0.6916 0.077 Uiso calc U . R 1 . .
C C21 0.7883(2) 0.5935(3) 0.59484(18) 0.0627(7) Uani d . . . 1 . .
H H21 0.7316 0.6526 0.5979 0.075 Uiso calc U . R 1 . .
C C22 0.84156(18) 0.4121(2) 0.53288(13) 0.0436(5) Uani d . . . 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
C7 S1 C8 . . 102.03(10)
C1 N1 C14 . . 128.3(2)
C21 N2 C22 . . 117.5(2)
O1 C1 N1 . . 124.4(2)
O1 C1 C2 . . 119.7(2)
N1 C1 C2 . . 116.0(2)
C7 C2 C3 . . 119.7(2)
C7 C2 C1 . . 122.75(19)
C3 C2 C1 . . 117.2(2)
C4 C3 C2 . . 119.5(2)
C5 C4 C3 . . 121.3(2)
C4 C5 C6 . . 119.2(2)
C5 C6 C7 . . 121.6(2)
C5 C6 Cl1 . . 117.6(2)
C7 C6 Cl1 . . 120.76(19)
C6 C7 C2 . . 118.6(2)
C6 C7 S1 . . 120.71(18)
C2 C7 S1 . . 120.51(17)
C13 C8 C9 . . 119.5(2)
C13 C8 S1 . . 124.42(18)
C9 C8 S1 . . 116.07(18)
C10 C9 C8 . . 120.1(3)
C9 C10 C11 . . 120.5(3)
C12 C11 C10 . . 119.5(3)
C11 C12 C13 . . 120.8(3)
C12 C13 C8 . . 119.7(2)
C15 C14 N1 . . 125.7(2)
C15 C14 C22 . . 119.7(2)
N1 C14 C22 . . 114.57(18)
C14 C15 C16 . . 119.4(2)
C17 C16 C15 . . 122.3(2)
C16 C17 C18 . . 119.9(2)
C17 C18 C22 . . 119.2(2)
C17 C18 C19 . . 124.1(2)
C22 C18 C19 . . 116.7(2)
C20 C19 C18 . . 120.0(2)
C19 C20 C21 . . 119.0(2)
N2 C21 C20 . . 123.7(2)
N2 C22 C18 . . 123.0(2)
N2 C22 C14 . . 117.41(18)
C18 C22 C14 . . 119.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C6 . 1.735(3)
S1 C7 . 1.765(2)
S1 C8 . 1.780(2)
O1 C1 . 1.215(3)
N1 C1 . 1.344(3)
N1 C14 . 1.407(3)
N2 C21 . 1.313(3)
N2 C22 . 1.362(3)
C1 C2 . 1.504(3)
C2 C7 . 1.396(3)
C2 C3 . 1.399(3)
C3 C4 . 1.387(4)
C4 C5 . 1.365(4)
C5 C6 . 1.376(4)
C6 C7 . 1.394(3)
C8 C13 . 1.384(3)
C8 C9 . 1.389(3)
C9 C10 . 1.377(4)
C10 C11 . 1.377(5)
C11 C12 . 1.376(4)
C12 C13 . 1.381(4)
C14 C15 . 1.376(3)
C14 C22 . 1.424(3)
C15 C16 . 1.402(4)
C16 C17 . 1.355(4)
C17 C18 . 1.405(3)
C18 C22 . 1.412(3)
C18 C19 . 1.413(4)
C19 C20 . 1.349(4)
C20 C21 . 1.408(4)
