#------------------------------------------------------------------------------
#$Date: 2022-11-15 01:02:50 +0200 (Tue, 15 Nov 2022) $
#$Revision: 279265 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/10/7131001.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_7131001
loop_
_publ_author_name
'Wu, Jiaping'
'Sun, Peng-Peng'
'Hong, Yuwen'
'Yang, Haitao'
'Xie, Meihua'
'Zhang, Jitan'
_publ_section_title
;
 Palladium-catalyzed Interannular C-H Amination of Biaryl Amines
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC05129J
_journal_year                    2022
_chemical_formula_sum            'C24 H24 N2 O3 S'
_chemical_formula_weight         420.51
_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'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2750jz
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2021-02-02 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.4750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.8985(3)
_cell_length_b                   22.3112(9)
_cell_length_c                   10.5503(5)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      2.96
_cell_volume                     2052.75(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            50315
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         2.888
_exptl_absorpt_coefficient_mu    0.187
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0083(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0555P)²+0.9400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3744
_reflns_number_total             4707
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc05129j2.cif
_cod_data_source_block           mo_20200731a_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7131001
_shelx_shelxl_version_number     2018/1
_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.
;
_shelx_estimated_absorpt_t_min   0.958
_shelx_estimated_absorpt_t_max   0.964
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_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
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5923(3) 0.13513(9) 0.5949(3) 0.0653(6) Uani 1 1 d . . . . .
H1A H 0.501919 0.111304 0.567196 0.098 Uiso 1 1 calc R U . . .
H1B H 0.635684 0.126296 0.683709 0.098 Uiso 1 1 calc R U . . .
H1C H 0.665823 0.126083 0.542280 0.098 Uiso 1 1 calc R U . . .
C2 C 0.5507(2) 0.20069(8) 0.58165(18) 0.0435(4) Uani 1 1 d . . . . .
C3 C 0.6551(2) 0.24428(8) 0.63622(19) 0.0459(4) Uani 1 1 d . . . . .
H3 H 0.749629 0.232536 0.684467 0.055 Uiso 1 1 calc R U . . .
C4 C 0.62216(19) 0.30457(8) 0.62065(18) 0.0414(4) Uani 1 1 d . . . . .
H4 H 0.694129 0.333012 0.657508 0.050 Uiso 1 1 calc R U . . .
C5 C 0.48119(18) 0.32248(7) 0.54978(15) 0.0318(3) Uani 1 1 d . . . . .
C6 C 0.3729(2) 0.27999(8) 0.49731(18) 0.0403(4) Uani 1 1 d . . . . .
H6 H 0.277022 0.291789 0.451766 0.048 Uiso 1 1 calc R U . . .
C7 C 0.4093(2) 0.21958(8) 0.5136(2) 0.0473(4) Uani 1 1 d . . . . .
H7 H 0.336872 0.191096 0.477818 0.057 Uiso 1 1 calc R U . . .
C8 C 0.46391(16) 0.42649(7) 0.77015(15) 0.0297(3) Uani 1 1 d . . . . .
C9 C 0.56741(19) 0.47333(8) 0.80340(19) 0.0408(4) Uani 1 1 d . . . . .
H9 H 0.572714 0.504064 0.744899 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6623(2) 0.47375(9) 0.9242(2) 0.0520(5) Uani 1 1 d . . . . .
H10 H 0.731393 0.504982 0.947748 0.062 Uiso 1 1 calc R U . . .
C11 C 0.6542(2) 0.42785(10) 1.0095(2) 0.0544(5) Uani 1 1 d . . . . .
H11 H 0.719452 0.427918 1.090185 0.065 Uiso 1 1 calc R U . . .
C12 C 0.5505(2) 0.38171(9) 0.97714(18) 0.0458(4) Uani 1 1 d . . . . .
H12 H 0.546029 0.351283 1.036525 0.055 Uiso 1 1 calc R U . . .
C13 C 0.45213(18) 0.38012(7) 0.85617(15) 0.0327(3) Uani 1 1 d . . . . .
C14 C 0.33922(18) 0.33123(7) 0.81991(15) 0.0318(3) Uani 1 1 d . . . . .
C15 C 0.3804(2) 0.27191(7) 0.85010(16) 0.0391(4) Uani 1 1 d . . . . .
H15 H 0.480616 0.263481 0.891212 0.047 Uiso 1 1 calc R U . . .
C16 C 0.2767(2) 0.22482(7) 0.82085(18) 0.0443(4) Uani 1 1 d . . . . .
C17 C 0.1289(2) 0.23857(8) 0.76076(19) 0.0469(5) Uani 1 1 d . . . . .
H17 H 0.057093 0.207933 0.741913 0.056 Uiso 1 1 calc R U . . .
C18 C 0.0844(2) 0.29714(8) 0.72753(18) 0.0402(4) Uani 1 1 d . . . . .
H18 H -0.015846 0.304964 0.685516 0.048 Uiso 1 1 calc R U . . .
C19 C 0.18808(18) 0.34413(7) 0.75644(15) 0.0310(3) Uani 1 1 d . . . . .
C20 C 0.3266(3) 0.16102(9) 0.8536(2) 0.0643(6) Uani 1 1 d . . . . .
H20A H 0.244906 0.139493 0.880471 0.096 Uiso 1 1 calc R U . . .
H20B H 0.415279 0.161005 0.922379 0.096 Uiso 1 1 calc R U . . .
H20C H 0.351351 0.142012 0.778711 0.096 Uiso 1 1 calc R U . . .
C21 C 0.20347(16) 0.43553(7) 0.62990(14) 0.0276(3) Uani 1 1 d . . . . .
H21 H 0.148348 0.421145 0.545638 0.033 Uiso 1 1 calc R U . . .
C22 C 0.18031(18) 0.50285(7) 0.64117(17) 0.0354(4) Uani 1 1 d . . . . .
H22A H 0.244734 0.517100 0.720603 0.042 Uiso 1 1 calc R U . . .
H22B H 0.213084 0.522773 0.569576 0.042 Uiso 1 1 calc R U . . .
C23 C -0.0323(2) 0.48739(8) 0.73731(18) 0.0417(4) Uani 1 1 d . . . . .
H23A H -0.139467 0.497624 0.731006 0.050 Uiso 1 1 calc R U . . .
H23B H 0.023004 0.499648 0.822035 0.050 Uiso 1 1 calc R U . . .
C24 C -0.01732(18) 0.42029(7) 0.72329(18) 0.0369(4) Uani 1 1 d . . . . .
H24A H -0.058009 0.399854 0.790309 0.044 Uiso 1 1 calc R U . . .
H24B H -0.075082 0.407402 0.639902 0.044 Uiso 1 1 calc R U . . .
N1 N 0.36804(14) 0.42458(6) 0.64312(12) 0.0285(3) Uani 1 1 d . . . . .
N2 N 0.14533(14) 0.40536(5) 0.73430(13) 0.0296(3) Uani 1 1 d . . . . .
O1 O 0.58836(15) 0.42802(6) 0.53301(15) 0.0520(4) Uani 1 1 d . . . . .
O2 O 0.32825(17) 0.40593(6) 0.40826(12) 0.0504(3) Uani 1 1 d . . . . .
O3 O 0.02613(13) 0.51881(5) 0.64096(13) 0.0427(3) Uani 1 1 d . . . . .
S1 S 0.44292(5) 0.39962(2) 0.52328(4) 0.03498(13) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 117.77(17) . . ?
C7 C2 C1 121.63(19) . . ?
C3 C2 C1 120.60(19) . . ?
C4 C3 C2 121.66(17) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.58(16) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.09(16) . . ?
C4 C5 S1 119.46(13) . . ?
C6 C5 S1 120.43(13) . . ?
C5 C6 C7 119.19(17) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C2 C7 C6 121.68(17) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C9 C8 C13 121.68(15) . . ?
C9 C8 N1 119.81(14) . . ?
C13 C8 N1 118.49(13) . . ?
C10 C9 C8 119.34(17) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 119.80(17) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.89(18) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 120.79(18) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 117.48(16) . . ?
C8 C13 C14 120.90(14) . . ?
C12 C13 C14 121.62(15) . . ?
C15 C14 C19 119.06(15) . . ?
C15 C14 C13 120.44(15) . . ?
C19 C14 C13 120.48(13) . . ?
C16 C15 C14 122.25(17) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C17 C16 C15 117.68(16) . . ?
C17 C16 C20 121.75(19) . . ?
C15 C16 C20 120.57(19) . . ?
C16 C17 C18 121.62(17) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 120.67(17) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 118.69(15) . . ?
C18 C19 N2 122.91(15) . . ?
C14 C19 N2 118.20(13) . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 N2 110.29(12) . . ?
N1 C21 C22 107.78(12) . . ?
N2 C21 C22 108.64(12) . . ?
N1 C21 H21 110.0 . . ?
N2 C21 H21 110.0 . . ?
C22 C21 H21 110.0 . . ?
O3 C22 C21 113.17(13) . . ?
O3 C22 H22A 108.9 . . ?
C21 C22 H22A 108.9 . . ?
O3 C22 H22B 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
O3 C23 C24 111.57(14) . . ?
O3 C23 H23A 109.3 . . ?
C24 C23 H23A 109.3 . . ?
O3 C23 H23B 109.3 . . ?
C24 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
N2 C24 C23 108.76(13) . . ?
N2 C24 H24A 109.9 . . ?
C23 C24 H24A 109.9 . . ?
N2 C24 H24B 109.9 . . ?
C23 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
C8 N1 C21 118.71(12) . . ?
C8 N1 S1 118.14(10) . . ?
C21 N1 S1 122.39(10) . . ?
C19 N2 C24 117.24(12) . . ?
C19 N2 C21 116.08(12) . . ?
C24 N2 C21 108.99(12) . . ?
C23 O3 C22 111.60(12) . . ?
O1 S1 O2 120.13(9) . . ?
O1 S1 N1 107.21(8) . . ?
O2 S1 N1 106.88(7) . . ?
O1 S1 C5 106.14(8) . . ?
O2 S1 C5 108.25(8) . . ?
N1 S1 C5 107.70(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.508(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C7 1.385(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.380(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(2) . ?
C5 S1 1.7661(16) . ?
C6 C7 1.389(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.391(2) . ?
C8 C13 1.394(2) . ?
C8 N1 1.4390(19) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.397(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.481(2) . ?
C14 C15 1.393(2) . ?
C14 C19 1.408(2) . ?
C15 C16 1.392(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(3) . ?
C16 C20 1.511(2) . ?
C17 C18 1.390(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.390(2) . ?
C18 H18 0.9300 . ?
C19 N2 1.4249(19) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N1 1.4637(18) . ?
C21 N2 1.4699(19) . ?
C21 C22 1.524(2) . ?
C21 H21 0.9800 . ?
C22 O3 1.4170(18) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 O3 1.416(2) . ?
C23 C24 1.513(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 N2 1.4671(19) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
N1 S1 1.6395(13) . ?
O1 S1 1.4262(13) . ?
O2 S1 1.4287(14) . ?
