#------------------------------------------------------------------------------
#$Date: 2019-11-25 15:32:59 +0200 (Mon, 25 Nov 2019) $
#$Revision: 241212 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/08/4130854.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_4130854
loop_
_publ_author_name
'Xie, Weilong'
'Yoon, Jung Hee'
'Chang, Sukbok'
_publ_section_title
;
 (NHC)Cu-Catalyzed Mild C-H Amidation of (Hetero)arenes with Deprotectable
 Carbamates: Scope and Mechanistic Studies.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12605
_journal_page_last               12614
_journal_paper_doi               10.1021/jacs.6b07486
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C12 H14 N2 O2 S'
_chemical_formula_weight         250.31
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 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                 94.893(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1687(2)
_cell_length_b                   22.8670(8)
_cell_length_c                   8.7061(3)
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      27.354
_cell_measurement_theta_min      2.957
_cell_volume                     1223.60(7)
_computing_cell_refinement       'Bruker SMART APEXll'
_computing_data_collection       'Bruker SMART APEXll'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega phi scan'
_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  0.1457
_diffrn_reflns_av_sigmaI/netI    0.0532
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            44087
_diffrn_reflns_theta_full        27.65
_diffrn_reflns_theta_max         27.65
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.9798
_exptl_absorpt_correction_T_min  0.9435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0367P)²+3.2826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1621
_refine_ls_wR_factor_ref         0.1746
_reflns_number_gt                2067
_reflns_number_total             2831
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja6b07486_si_005.cif
_cod_data_source_block           p21c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4130854
_shelx_estimated_absorpt_t_min   0.943
_shelx_estimated_absorpt_t_max   0.980
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.4708(6) 0.40433(16) 0.2861(4) 0.0275(8) Uani 1 1 d .
C2 C 0.2877(5) 0.48967(15) 0.1803(4) 0.0243(7) Uani 1 1 d .
C3 C -0.0326(6) 0.54768(16) 0.2217(4) 0.0274(8) Uani 1 1 d .
C4 C -0.2200(6) 0.57693(17) 0.2551(4) 0.0319(8) Uani 1 1 d .
H4 H -0.3036 0.5635 0.3348 0.038 Uiso 1 1 calc R
C5 C -0.2821(6) 0.62592(18) 0.1698(4) 0.0342(9) Uani 1 1 d .
H5 H -0.4097 0.6467 0.1909 0.041 Uiso 1 1 calc R
C6 C -0.1584(6) 0.64515(18) 0.0528(4) 0.0349(9) Uani 1 1 d .
H6 H -0.2033 0.6789 -0.0051 0.042 Uiso 1 1 calc R
C7 C 0.0276(6) 0.61608(16) 0.0198(4) 0.0311(8) Uani 1 1 d .
H7 H 0.1112 0.6298 -0.0595 0.037 Uiso 1 1 calc R
C8 C 0.0915(6) 0.56649(15) 0.1035(4) 0.0258(7) Uani 1 1 d .
C9 C 0.7038(6) 0.32308(16) 0.3741(4) 0.0307(8) Uani 1 1 d .
C10 C 0.8983(7) 0.29574(19) 0.3070(5) 0.0446(11) Uani 1 1 d .
H10A H 0.8552 0.2815 0.2027 0.067 Uiso 1 1 calc R
H10B H 0.9522 0.2630 0.3721 0.067 Uiso 1 1 calc R
H10C H 1.0135 0.3251 0.3027 0.067 Uiso 1 1 calc R
C11 C 0.7717(8) 0.3517(2) 0.5281(5) 0.0498(12) Uani 1 1 d .
H11A H 0.8323 0.3221 0.6008 0.075 Uiso 1 1 calc R
H11B H 0.6447 0.3700 0.5687 0.075 Uiso 1 1 calc R
H11C H 0.8821 0.3817 0.5140 0.075 Uiso 1 1 calc R
C12 C 0.5242(7) 0.27827(18) 0.3826(5) 0.0453(11) Uani 1 1 d .
H12A H 0.4728 0.2656 0.2783 0.068 Uiso 1 1 calc R
H12B H 0.4032 0.2958 0.4325 0.068 Uiso 1 1 calc R
H12C H 0.5803 0.2444 0.4426 0.068 Uiso 1 1 calc R
N1 N 0.2724(5) 0.53216(13) 0.0814(3) 0.0256(6) Uani 1 1 d .
N2 N 0.4532(5) 0.44950(13) 0.1826(3) 0.0268(7) Uani 1 1 d .
H2 H 0.5513 0.4529 0.1154 0.032 Uiso 1 1 calc R
O1 O 0.3484(5) 0.39799(12) 0.3863(3) 0.0397(7) Uani 1 1 d .
O2 O 0.6367(4) 0.36926(11) 0.2597(3) 0.0295(6) Uani 1 1 d .
S1 S 0.08534(16) 0.48598(4) 0.31003(10) 0.0303(3) Uani 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 0.0033 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
O1 C1 O2 125.9(3)
O1 C1 N2 123.1(3)
O2 C1 N2 111.0(3)
N1 C2 N2 121.6(3)
N1 C2 S1 116.6(3)
N2 C2 S1 121.8(3)
C4 C3 C8 121.5(3)
C4 C3 S1 128.6(3)
C8 C3 S1 109.9(3)
C5 C4 C3 118.5(3)
C5 C4 H4 120.8
C3 C4 H4 120.8
C4 C5 C6 120.3(4)
C4 C5 H5 119.8
C6 C5 H5 119.8
C7 C6 C5 121.2(4)
C7 C6 H6 119.4
C5 C6 H6 119.4
C6 C7 C8 119.3(3)
C6 C7 H7 120.4
C8 C7 H7 120.4
C7 C8 N1 125.7(3)
C7 C8 C3 119.2(3)
N1 C8 C3 115.0(3)
O2 C9 C10 102.7(3)
O2 C9 C12 110.5(3)
C10 C9 C12 110.3(3)
O2 C9 C11 109.0(3)
C10 C9 C11 110.5(4)
C12 C9 C11 113.3(4)
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C2 N1 C8 110.2(3)
C1 N2 C2 122.1(3)
C1 N2 H2 118.9
C2 N2 H2 118.9
C1 O2 C9 119.0(3)
C3 S1 C2 88.28(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.210(4)
C1 O2 1.336(4)
C1 N2 1.369(4)
C2 N1 1.296(4)
C2 N2 1.372(4)
C2 S1 1.755(3)
C3 C4 1.388(5)
C3 C8 1.401(5)
C3 S1 1.737(4)
C4 C5 1.380(6)
C4 H4 0.9500
C5 C6 1.395(5)
C5 H5 0.9500
C6 C7 1.378(5)
C6 H6 0.9500
C7 C8 1.387(5)
C7 H7 0.9500
C8 N1 1.391(4)
C9 O2 1.486(4)
C9 C10 1.514(6)
C9 C12 1.516(5)
C9 C11 1.519(6)
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 H11A 0.9800
C11 H11B 0.9800
C11 H11C 0.9800
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
N2 H2 0.8800
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
C8 C3 C4 C5 -0.6(6)
S1 C3 C4 C5 179.3(3)
C3 C4 C5 C6 0.1(6)
C4 C5 C6 C7 -0.2(6)
C5 C6 C7 C8 0.7(6)
C6 C7 C8 N1 178.7(3)
C6 C7 C8 C3 -1.1(5)
C4 C3 C8 C7 1.1(5)
S1 C3 C8 C7 -178.8(3)
C4 C3 C8 N1 -178.7(3)
S1 C3 C8 N1 1.3(4)
N2 C2 N1 C8 -179.9(3)
S1 C2 N1 C8 0.4(4)
C7 C8 N1 C2 179.0(4)
C3 C8 N1 C2 -1.1(4)
O1 C1 N2 C2 -3.2(6)
O2 C1 N2 C2 176.3(3)
N1 C2 N2 C1 -179.8(3)
S1 C2 N2 C1 -0.2(5)
O1 C1 O2 C9 -9.9(6)
N2 C1 O2 C9 170.6(3)
C10 C9 O2 C1 -177.4(3)
C12 C9 O2 C1 65.0(4)
C11 C9 O2 C1 -60.2(4)
C4 C3 S1 C2 179.2(4)
C8 C3 S1 C2 -0.9(3)
N1 C2 S1 C3 0.3(3)
N2 C2 S1 C3 -179.4(3)
