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#$Date: 2021-04-05 17:11:47 +0300 (Mon, 05 Apr 2021) $
#$Revision: 263664 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/00/1560098.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_1560098
loop_
_publ_author_name
'Wang, Yandong'
'Bai, Jingyi'
'Yang, Youqing'
'Zhao, Wenxuan'
'Liang, Yong'
'Wang, Di'
'Zhao, Yue'
'Shi, Zhuangzhi'
_publ_section_title
;
 Rhodium-catalysed selective C--C bond activation and borylation of
 cyclopropanes
;
_journal_issue                   10
_journal_name_full               'Chemical Science'
_journal_page_first              3599
_journal_page_last               3607
_journal_paper_doi               10.1039/D0SC06186G
_journal_volume                  12
_journal_year                    2021
_chemical_formula_sum            'C22 H34 Cl2 N2 O6 Rh2'
_chemical_formula_weight         699.23
_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_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-09-16 deposited with the CCDC.	2021-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.0060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.2163(4)
_cell_length_b                   11.7129(5)
_cell_length_c                   13.3216(5)
_cell_measurement_reflns_used    5684
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.37
_cell_volume                     1367.63(10)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(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  0.0391
_diffrn_reflns_av_unetI/netI     0.0346
_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       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12154
_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         27.492
_diffrn_reflns_theta_min         2.368
_exptl_absorpt_coefficient_mu    1.440
_exptl_crystal_density_diffrn    1.698
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.028
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         3123
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0292
_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)+(0.0374P)²+0.5681P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0804
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2756
_reflns_number_total             3123
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc06186g2.cif
_cod_data_source_block           20200728ZH_SZZ_WS64_0m_a
_cod_depositor_comments
'Adding full bibliography for 1560097--1560099.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1560098
_shelx_shelxl_version_number     2018/3
_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   0.846
_shelx_estimated_absorpt_t_max   0.894
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
Rh01 Rh 0.66526(2) 0.58777(2) 0.56807(2) 0.02539(9) Uani 1 1 d . . . . .
Cl1 Cl 0.44366(9) 0.60755(7) 0.40649(6) 0.03428(18) Uani 1 1 d . . . . .
O1 O 0.5442(2) 0.65445(19) 0.65899(15) 0.0321(5) Uani 1 1 d . . . . .
O3 O 0.8408(3) 0.4948(2) 0.43325(17) 0.0483(7) Uani 1 1 d . . . . .
O2 O 0.7148(3) 0.8077(2) 0.4921(2) 0.0573(7) Uani 1 1 d . . . . .
N1 N 0.7470(3) 0.6012(2) 0.79056(19) 0.0340(6) Uani 1 1 d . . . . .
C7 C 0.8259(3) 0.5748(3) 0.7107(2) 0.0326(7) Uani 1 1 d . . . . .
H7 H 0.866343 0.496834 0.721079 0.039 Uiso 1 1 calc R U . . .
C10 C 0.7604(4) 0.7413(3) 0.5653(3) 0.0368(7) Uani 1 1 d . . . . .
C5 C 0.6080(3) 0.6424(3) 0.7570(2) 0.0311(6) Uani 1 1 d . . . . .
C11 C 0.7779(3) 0.5293(3) 0.4871(2) 0.0326(7) Uani 1 1 d . . . . .
C2 C 0.5084(4) 0.6735(3) 0.8274(3) 0.0390(8) Uani 1 1 d . . . . .
C6 C 0.8380(4) 0.5765(3) 0.9002(3) 0.0472(9) Uani 1 1 d . . . . .
H6A H 0.914540 0.520689 0.900762 0.071 Uiso 1 1 calc R U . . .
H6B H 0.772570 0.547319 0.938039 0.071 Uiso 1 1 calc R U . . .
H6C H 0.886268 0.645278 0.933478 0.071 Uiso 1 1 calc R U . . .
C3 C 0.4424(5) 0.5618(4) 0.8535(3) 0.0563(11) Uani 1 1 d . . . . .
H3A H 0.394279 0.520766 0.789464 0.084 Uiso 1 1 calc R U . . .
H3B H 0.368538 0.578163 0.888910 0.084 Uiso 1 1 calc R U . . .
H3C H 0.523032 0.516182 0.898582 0.084 Uiso 1 1 calc R U . . .
C8 C 0.9537(4) 0.6583(4) 0.7163(3) 0.0498(10) Uani 1 1 d . . . . .
H8A H 1.009994 0.674111 0.789420 0.060 Uiso 1 1 calc R U . . .
H8B H 1.023576 0.625584 0.682659 0.060 Uiso 1 1 calc R U . . .
C1 C 0.3756(5) 0.7476(4) 0.7615(3) 0.0570(11) Uani 1 1 d . . . . .
H1A H 0.415132 0.816072 0.740027 0.085 Uiso 1 1 calc R U . . .
H1B H 0.310820 0.767250 0.803131 0.085 Uiso 1 1 calc R U . . .
H1C H 0.317805 0.705897 0.700140 0.085 Uiso 1 1 calc R U . . .
C9 C 0.8886(5) 0.7647(4) 0.6625(3) 0.0551(11) Uani 1 1 d . . . . .
H9A H 0.967363 0.807066 0.644218 0.066 Uiso 1 1 calc R U . . .
H9B H 0.852446 0.811495 0.709906 0.066 Uiso 1 1 calc R U . . .
C4 C 0.5927(5) 0.7398(4) 0.9271(3) 0.0621(12) Uani 1 1 d . . . . .
H4A H 0.656046 0.688462 0.978297 0.093 Uiso 1 1 calc R U . . .
H4B H 0.519937 0.774979 0.955672 0.093 Uiso 1 1 calc R U . . .
H4C H 0.655008 0.797667 0.910043 0.093 Uiso 1 1 calc R U . . .
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'
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
C11 Rh01 C10 89.65(13) . . ?
C11 Rh01 C7 98.06(13) . . ?
C10 Rh01 C7 83.53(14) . . ?
C11 Rh01 O1 178.87(11) . . ?
C10 Rh01 O1 89.43(10) . . ?
C7 Rh01 O1 81.19(10) . . ?
C11 Rh01 Cl1 89.35(9) . . ?
C10 Rh01 Cl1 98.49(10) . . ?
C7 Rh01 Cl1 172.34(9) . . ?
O1 Rh01 Cl1 91.43(6) . . ?
C11 Rh01 Cl1 93.44(10) . 3_666 ?
C10 Rh01 Cl1 173.77(10) . 3_666 ?
C7 Rh01 Cl1 90.68(10) . 3_666 ?
O1 Rh01 Cl1 87.41(7) . 3_666 ?
Cl1 Rh01 Cl1 86.96(3) . 3_666 ?
Rh01 Cl1 Rh01 93.04(3) . 3_666 ?
C5 O1 Rh01 113.97(19) . . ?
C5 N1 C6 127.4(3) . . ?
C5 N1 C7 118.2(2) . . ?
C6 N1 C7 114.4(3) . . ?
N1 C7 C8 111.9(3) . . ?
N1 C7 Rh01 106.10(19) . . ?
C8 C7 Rh01 109.3(2) . . ?
N1 C7 H7 109.8 . . ?
C8 C7 H7 109.8 . . ?
Rh01 C7 H7 109.8 . . ?
O2 C10 C9 124.5(3) . . ?
O2 C10 Rh01 122.9(3) . . ?
C9 C10 Rh01 112.6(3) . . ?
O1 C5 N1 119.1(3) . . ?
O1 C5 C2 115.3(3) . . ?
N1 C5 C2 125.5(3) . . ?
O3 C11 Rh01 176.5(3) . . ?
C4 C2 C3 111.6(3) . . ?
C4 C2 C1 108.1(3) . . ?
C3 C2 C1 108.1(3) . . ?
C4 C2 C5 114.2(3) . . ?
C3 C2 C5 106.8(3) . . ?
C1 C2 C5 107.7(3) . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C9 C8 C7 109.3(3) . . ?
C9 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
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 . . ?
C8 C9 C10 111.3(3) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
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
Rh01 C11 1.845(3) . ?
Rh01 C10 2.006(3) . ?
Rh01 C7 2.021(3) . ?
Rh01 O1 2.0387(19) . ?
Rh01 Cl1 2.4779(8) . ?
Rh01 Cl1 2.5625(8) 3_666 ?
O1 C5 1.263(4) . ?
O3 C11 1.128(3) . ?
O2 C10 1.216(4) . ?
N1 C5 1.311(4) . ?
N1 C6 1.471(4) . ?
N1 C7 1.495(4) . ?
C7 C8 1.515(5) . ?
C7 H7 0.9800 . ?
C10 C9 1.484(5) . ?
C5 C2 1.545(4) . ?
C2 C4 1.527(5) . ?
C2 C3 1.528(5) . ?
C2 C1 1.536(5) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C8 C9 1.470(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
