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#$Date: 2025-04-03 08:32:21 +0300 (Thu, 03 Apr 2025) $
#$Revision: 298703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/35/7713576.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_7713576
loop_
_publ_author_name
'Jiménez, M. Victoria'
'González-Lainez, Miguel'
'Passarelli, Vincenzo'
'Pérez-Torrente, Jesús J.'
_publ_section_title
;
 β-(Z)-Selective Alkyne Hydrosilylation by a N,O-Functionalized NHC-based
 Rhodium(I) Catalyst
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT01911J
_journal_year                    2023
_chemical_formula_moiety         'C16 H21 Br N3 O2 Rh'
_chemical_formula_sum            'C16 H21 Br N3 O2 Rh'
_chemical_formula_weight         490.17
_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     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2023-03-15 deposited with the CCDC.	2023-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.1460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9388(8)
_cell_length_b                   9.9973(7)
_cell_length_c                   14.8252(10)
_cell_measurement_reflns_used    5227
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.152
_cell_measurement_theta_min      2.494
_cell_volume                     1690.8(2)
_computing_cell_refinement       'APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_data_collection       'APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_data_reduction        'APEX2 v. 2008.4 (Bruker AXS, 2008)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ENCIFER
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker SMART APEX CCD system'
_diffrn_measurement_method       'ω rotations with narrow frames'
_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  0.0385
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19228
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.538
_diffrn_reflns_theta_min         2.494
_exptl_absorpt_coefficient_mu    3.386
_exptl_absorpt_correction_T_max  0.6656
_exptl_absorpt_correction_T_min  0.5582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Multi-scan correction included in APEX2 package (Bruker AXS, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.667
_refine_diff_density_min         -1.196
_refine_diff_density_rms         0.119
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0321
_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)+(0.0367P)²+2.9743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0801
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3442
_reflns_number_total             4097
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt01911j3.cif
_cod_data_source_block           cmpd_6_VPX83
_cod_depositor_comments
;

2025-04-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C32 H42 Br2 N6 O4 Rh2'
_cod_original_formula_weight         940.35
_cod_original_formula_moiety         'C32 H42 Br2 N6 O4 Rh2'
_cod_original_formula_units_Z            2
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7713576
_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.
;
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 0.0716(3) 0.2714(3) 0.2748(2) 0.0146(6) Uani 1 1 d . . . . .
C3 C 0.1209(3) 0.4622(3) 0.3577(2) 0.0162(6) Uani 1 1 d . . . . .
H3 H 0.1137 0.5450 0.3869 0.019 Uiso 1 1 calc R U . . .
C4 C 0.2214(3) 0.4043(3) 0.3559(2) 0.0163(6) Uani 1 1 d . . . . .
H4 H 0.2986 0.4367 0.3843 0.020 Uiso 1 1 calc R U . . .
C6 C -0.0987(3) 0.4113(3) 0.2958(2) 0.0180(7) Uani 1 1 d . . . . .
C7 C -0.1441(3) 0.4896(4) 0.2048(3) 0.0236(7) Uani 1 1 d . . . . .
H7A H -0.0972 0.5710 0.2083 0.035 Uiso 1 1 calc R U . . .
H7B H -0.2262 0.5140 0.1956 0.035 Uiso 1 1 calc R U . . .
H7C H -0.1382 0.4345 0.1517 0.035 Uiso 1 1 calc R U . . .
C8 C -0.1675(3) 0.2818(3) 0.2962(2) 0.0190(7) Uani 1 1 d . . . . .
H8A H -0.1647 0.2258 0.2426 0.028 Uiso 1 1 calc R U . . .
H8B H -0.2492 0.3035 0.2910 0.028 Uiso 1 1 calc R U . . .
H8C H -0.1324 0.2332 0.3552 0.028 Uiso 1 1 calc R U . . .
C9 C -0.1081(3) 0.4946(4) 0.3797(3) 0.0267(8) Uani 1 1 d . . . . .
H9A H -0.0737 0.4449 0.4383 0.040 Uiso 1 1 calc R U . . .
H9B H -0.1908 0.5132 0.3729 0.040 Uiso 1 1 calc R U . . .
H9C H -0.0659 0.5791 0.3817 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2687(3) 0.1854(3) 0.2872(2) 0.0171(6) Uani 1 1 d . . . . .
H10A H 0.3507 0.2172 0.3103 0.021 Uiso 1 1 calc R U . . .
H10B H 0.2499 0.1689 0.2185 0.021 Uiso 1 1 calc R U . . .
C11 C 0.2562(3) 0.0564(3) 0.3369(2) 0.0149(6) Uani 1 1 d . . . . .
C13 C 0.1284(3) -0.0891(3) 0.3789(2) 0.0152(6) Uani 1 1 d . . . . .
C14 C 0.2220(3) -0.1585(3) 0.4391(2) 0.0186(7) Uani 1 1 d . . . . .
H14 H 0.2082 -0.2311 0.4758 0.022 Uiso 1 1 calc R U . . .
C15 C 0.3353(3) -0.1204(3) 0.4449(2) 0.0195(7) Uani 1 1 d . . . . .
H15 H 0.4003 -0.1697 0.4826 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3528(3) -0.0088(3) 0.3946(2) 0.0164(6) Uani 1 1 d . . . . .
H16 H 0.4298 0.0220 0.3999 0.020 Uiso 1 1 calc R U . . .
C17 C 0.0036(3) -0.1177(3) 0.3753(2) 0.0200(7) Uani 1 1 d . . . . .
H17A H -0.0414 -0.0332 0.3676 0.024 Uiso 1 1 calc R U . . .
H17B H -0.0334 -0.1764 0.3209 0.024 Uiso 1 1 calc R U . . .
C19 C -0.1125(3) -0.1819(4) 0.4703(3) 0.0224(7) Uani 1 1 d . . . . .
H19A H -0.1382 -0.0896 0.4745 0.034 Uiso 1 1 calc R U . . .
H19B H -0.1121 -0.2306 0.5277 0.034 Uiso 1 1 calc R U . . .
H19C H -0.1664 -0.2258 0.4154 0.034 Uiso 1 1 calc R U . . .
C20 C -0.0724(3) 0.1869(3) 0.1018(2) 0.0177(7) Uani 1 1 d . . . . .
N2 N 0.0283(2) 0.3791(3) 0.30896(19) 0.0137(5) Uani 1 1 d . . . . .
N5 N 0.1902(2) 0.2880(3) 0.30440(19) 0.0141(5) Uani 1 1 d . . . . .
N12 N 0.1456(2) 0.0130(3) 0.32490(18) 0.0144(5) Uani 1 1 d . . . . .
O18 O 0.0027(2) -0.1813(3) 0.46039(17) 0.0228(5) Uani 1 1 d . . . . .
O21 O -0.1206(2) 0.2434(3) 0.03475(17) 0.0264(6) Uani 1 1 d . . . . .
Br1 Br -0.04905(3) -0.12043(3) 0.12871(3) 0.02292(10) Uani 1 1 d . . . . .
Rh1 Rh 0.01292(2) 0.10150(2) 0.20774(2) 0.01256(8) 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh -1.1178 0.9187 '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
N2 C1 N5 104.9(3) . . ?
N2 C1 Rh1 138.5(2) . . ?
N5 C1 Rh1 116.3(2) . . ?
C4 C3 N2 108.0(3) . . ?
C4 C3 H3 126.0 . . ?
N2 C3 H3 126.0 . . ?
C3 C4 N5 106.1(3) . . ?
C3 C4 H4 126.9 . . ?
N5 C4 H4 126.9 . . ?
N2 C6 C7 107.9(3) . . ?
N2 C6 C9 108.9(3) . . ?
C7 C6 C9 110.5(3) . . ?
N2 C6 C8 109.8(3) . . ?
C7 C6 C8 112.8(3) . . ?
C9 C6 C8 106.8(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N5 C10 C11 110.6(3) . . ?
N5 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
N5 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
N12 C11 C16 122.5(3) . . ?
N12 C11 C10 116.2(3) . . ?
C16 C11 C10 121.3(3) . . ?
N12 C13 C14 121.6(3) . . ?
N12 C13 C17 116.5(3) . . ?
C14 C13 C17 121.8(3) . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 119.1(3) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C15 118.7(3) . . ?
C11 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
O18 C17 C13 108.8(3) . . ?
O18 C17 H17A 109.9 . . ?
C13 C17 H17A 109.9 . . ?
O18 C17 H17B 109.9 . . ?
C13 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
O18 C19 H19A 109.5 . . ?
O18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O21 C20 Rh1 176.3(3) . . ?
C1 N2 C3 109.5(3) . . ?
C1 N2 C6 127.0(3) . . ?
C3 N2 C6 123.5(3) . . ?
C1 N5 C4 111.4(3) . . ?
C1 N5 C10 121.2(3) . . ?
C4 N5 C10 127.2(3) . . ?
C13 N12 C11 118.5(3) . . ?
C13 N12 Rh1 125.6(2) . . ?
C11 N12 Rh1 115.5(2) . . ?
C17 O18 C19 110.8(3) . . ?
C20 Rh1 C1 93.21(14) . . ?
C20 Rh1 N12 168.08(12) . . ?
C1 Rh1 N12 83.17(11) . . ?
C20 Rh1 Br1 89.94(10) . . ?
C1 Rh1 Br1 176.31(9) . . ?
N12 Rh1 Br1 93.36(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 N2 1.355(4) . ?
C1 N5 1.363(4) . ?
C1 Rh1 1.988(3) . ?
C3 C4 1.340(5) . ?
C3 N2 1.402(4) . ?
C3 H3 0.9500 . ?
C4 N5 1.381(4) . ?
C4 H4 0.9500 . ?
C6 N2 1.505(4) . ?
C6 C7 1.515(5) . ?
C6 C9 1.528(5) . ?
C6 C8 1.534(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 N5 1.461(4) . ?
C10 C11 1.515(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 N12 1.350(4) . ?
C11 C16 1.380(4) . ?
C13 N12 1.350(4) . ?
C13 C14 1.392(5) . ?
C13 C17 1.503(4) . ?
C14 C15 1.384(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.391(5) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O18 1.415(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C19 O18 1.426(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O21 1.140(4) . ?
C20 Rh1 1.814(3) . ?
N12 Rh1 2.165(3) . ?
Br1 Rh1 2.5162(4) . ?
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
N2 C3 C4 N5 1.3(3) . . . . ?
N5 C10 C11 N12 48.2(4) . . . . ?
N5 C10 C11 C16 -128.9(3) . . . . ?
N12 C13 C14 C15 1.0(5) . . . . ?
C17 C13 C14 C15 -174.7(3) . . . . ?
C13 C14 C15 C16 3.8(5) . . . . ?
N12 C11 C16 C15 -2.4(5) . . . . ?
C10 C11 C16 C15 174.5(3) . . . . ?
C14 C15 C16 C11 -3.2(5) . . . . ?
N12 C13 C17 O18 -154.8(3) . . . . ?
C14 C13 C17 O18 21.1(4) . . . . ?
N5 C1 N2 C3 1.1(3) . . . . ?
Rh1 C1 N2 C3 174.8(3) . . . . ?
N5 C1 N2 C6 179.3(3) . . . . ?
Rh1 C1 N2 C6 -7.1(5) . . . . ?
C4 C3 N2 C1 -1.6(4) . . . . ?
C4 C3 N2 C6 -179.8(3) . . . . ?
C7 C6 N2 C1 -87.6(4) . . . . ?
C9 C6 N2 C1 152.4(3) . . . . ?
C8 C6 N2 C1 35.8(4) . . . . ?
C7 C6 N2 C3 90.3(4) . . . . ?
C9 C6 N2 C3 -29.7(4) . . . . ?
C8 C6 N2 C3 -146.4(3) . . . . ?
N2 C1 N5 C4 -0.3(3) . . . . ?
Rh1 C1 N5 C4 -175.6(2) . . . . ?
N2 C1 N5 C10 175.3(3) . . . . ?
Rh1 C1 N5 C10 0.0(4) . . . . ?
C3 C4 N5 C1 -0.7(4) . . . . ?
C3 C4 N5 C10 -175.9(3) . . . . ?
C11 C10 N5 C1 -62.4(4) . . . . ?
C11 C10 N5 C4 112.4(3) . . . . ?
C14 C13 N12 C11 -6.4(5) . . . . ?
C17 C13 N12 C11 169.5(3) . . . . ?
C14 C13 N12 Rh1 166.1(2) . . . . ?
C17 C13 N12 Rh1 -18.0(4) . . . . ?
C16 C11 N12 C13 7.2(5) . . . . ?
C10 C11 N12 C13 -169.9(3) . . . . ?
C16 C11 N12 Rh1 -166.1(2) . . . . ?
C10 C11 N12 Rh1 16.9(3) . . . . ?
C13 C17 O18 C19 166.2(3) . . . . ?
