#------------------------------------------------------------------------------
#$Date: 2023-09-05 22:23:20 +0300 (Tue, 05 Sep 2023) $
#$Revision: 286076 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/96/1569605.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_1569605
loop_
_publ_author_name
'Peng, Marie'
'Ari, Denis'
'Roisnel, Thierry'
'Doucet, Henri'
'Soulé, Jean-François'
_publ_section_title
;
 Rhodium(i)-catalyzed cascade C(sp²)-H bond alkylation -
 amidation of anilines: phosphorus as traceless directing group.
;
_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              9055
_journal_page_last               9062
_journal_paper_doi               10.1039/d3sc02992a
_journal_volume                  14
_journal_year                    2023
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H10 Cl N O'
_chemical_formula_sum            'C10 H10 Cl N O'
_chemical_formula_weight         195.64
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2023-03-29 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.950(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4075(13)
_cell_length_b                   6.8598(8)
_cell_length_c                   12.7321(15)
_cell_measurement_reflns_used    1745
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4352
_cell_measurement_theta_min      2.8334
_cell_measurement_wavelength     0.710730
_cell_volume                     889.29(19)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_orient_matrix_UB_11      0.0818586
_diffrn_orient_matrix_UB_12      -0.0669256
_diffrn_orient_matrix_UB_13      -0.0102692
_diffrn_orient_matrix_UB_21      0.0525803
_diffrn_orient_matrix_UB_22      0.1178187
_diffrn_orient_matrix_UB_23      0.0281303
_diffrn_orient_matrix_UB_31      0.0133342
_diffrn_orient_matrix_UB_32      -0.0537339
_diffrn_orient_matrix_UB_33      0.0744698
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5583
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.271
_diffrn_source_current           1.0
_diffrn_source_power             50.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0404P)²+0.0687P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                1555
_reflns_number_total             2024
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3sc02992a2.cif
_cod_data_source_block           2AD24
_cod_depositor_comments          'Adding full bibliography for 1569605.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1569605
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 0.20350(17) 0.3008(2) 0.31215(14) 0.0186(4) Uani 1 1 d . . . . .
C2 C 0.25727(19) 0.2731(2) 0.41956(14) 0.0224(4) Uani 1 1 d . . . . .
H2 H 0.203091 0.262471 0.470866 0.027 Uiso 1 1 calc R U . . .
C3 C 0.39310(19) 0.2614(2) 0.45036(14) 0.0224(4) Uani 1 1 d . . . . .
H3 H 0.431700 0.243915 0.524170 0.027 Uiso 1 1 calc R U . . .
C4 C 0.47394(17) 0.2742(2) 0.37708(14) 0.0187(4) Uani 1 1 d . . . . .
C5 C 0.62048(18) 0.2550(3) 0.40815(14) 0.0238(4) Uani 1 1 d . . . . .
H5A H 0.645983 0.117537 0.400489 0.029 Uiso 1 1 calc R U . . .
H5B H 0.650880 0.293381 0.484199 0.029 Uiso 1 1 calc R U . . .
C6 C 0.68515(18) 0.3844(3) 0.33698(14) 0.0240(4) Uani 1 1 d . . . . .
H6A H 0.672877 0.522647 0.354892 0.029 Uiso 1 1 calc R U . . .
H6B H 0.780669 0.357490 0.351907 0.029 Uiso 1 1 calc R U . . .
C7 C 0.62970(18) 0.3524(2) 0.21967(14) 0.0212(4) Uani 1 1 d . . . . .
O8 O 0.69739(13) 0.36653(19) 0.15189(10) 0.0280(3) Uani 1 1 d . . . . .
N9 N 0.49846(14) 0.30947(19) 0.19206(11) 0.0179(3) Uani 1 1 d . . . . .
C10 C 0.43918(19) 0.2792(3) 0.07844(14) 0.0253(4) Uani 1 1 d . . . . .
H10A H 0.389347 0.395566 0.049867 0.038 Uiso 1 1 calc R U . . .
H10B H 0.380061 0.166568 0.071122 0.038 Uiso 1 1 calc R U . . .
H10C H 0.508472 0.255209 0.038335 0.038 Uiso 1 1 calc R U . . .
C11 C 0.41655(17) 0.3017(2) 0.26857(13) 0.0166(4) Uani 1 1 d . . . . .
C12 C 0.28083(17) 0.3170(2) 0.23605(13) 0.0174(4) Uani 1 1 d . . . . .
H12 H 0.241673 0.338169 0.162665 0.021 Uiso 1 1 calc R U . . .
Cl1 Cl 0.03318(4) 0.31479(6) 0.26990(4) 0.02514(15) 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'
Cl Cl 0.1484 0.1585 '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'
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 C12 121.93(16) . . ?
C2 C1 Cl1 119.40(13) . . ?
C12 C1 Cl1 118.67(13) . . ?
C1 C2 C3 117.92(16) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 122.13(17) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C11 118.67(16) . . ?
C3 C4 C5 122.96(16) . . ?
C11 C4 C5 118.35(15) . . ?
C4 C5 C6 110.06(14) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
C7 C6 C5 112.39(15) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
O8 C7 N9 121.62(16) . . ?
O8 C7 C6 122.02(17) . . ?
N9 C7 C6 116.36(15) . . ?
C7 N9 C11 122.65(14) . . ?
C7 N9 C10 118.52(14) . . ?
C11 N9 C10 118.77(14) . . ?
N9 C10 H10A 109.5 . . ?
N9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C4 120.23(16) . . ?
C12 C11 N9 120.60(15) . . ?
C4 C11 N9 119.16(15) . . ?
C1 C12 C11 119.11(16) . . ?
C1 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
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 1.379(2) . ?
C1 C12 1.386(2) . ?
C1 Cl1 1.7452(18) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C11 1.400(2) . ?
C4 C5 1.500(2) . ?
C5 C6 1.521(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.502(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O8 1.226(2) . ?
C7 N9 1.370(2) . ?
N9 C11 1.422(2) . ?
N9 C10 1.465(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.391(2) . ?
C12 H12 0.9500 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C1 C2 C3 -0.1(2) . . . . ?
Cl1 C1 C2 C3 179.58(13) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C11 0.6(3) . . . . ?
C2 C3 C4 C5 -177.86(16) . . . . ?
C3 C4 C5 C6 -146.70(16) . . . . ?
C11 C4 C5 C6 34.8(2) . . . . ?
C4 C5 C6 C7 -51.5(2) . . . . ?
C5 C6 C7 O8 -146.43(17) . . . . ?
C5 C6 C7 N9 34.5(2) . . . . ?
O8 C7 N9 C11 -176.84(15) . . . . ?
C6 C7 N9 C11 2.2(2) . . . . ?
O8 C7 N9 C10 0.3(2) . . . . ?
C6 C7 N9 C10 179.30(15) . . . . ?
C3 C4 C11 C12 0.4(2) . . . . ?
C5 C4 C11 C12 178.94(15) . . . . ?
C3 C4 C11 N9 -178.20(15) . . . . ?
C5 C4 C11 N9 0.3(2) . . . . ?
C7 N9 C11 C12 160.32(15) . . . . ?
C10 N9 C11 C12 -16.8(2) . . . . ?
C7 N9 C11 C4 -21.1(2) . . . . ?
C10 N9 C11 C4 161.81(15) . . . . ?
C2 C1 C12 C11 1.1(2) . . . . ?
Cl1 C1 C12 C11 -178.60(12) . . . . ?
C4 C11 C12 C1 -1.2(2) . . . . ?
N9 C11 C12 C1 177.37(14) . . . . ?
