#------------------------------------------------------------------------------
#$Date: 2025-08-19 01:15:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301787 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/00/1560097.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_1560097
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            'C21 H30 B F2 N O5'
_chemical_formula_weight         425.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 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                 94.364(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.1856(8)
_cell_length_b                   17.0247(8)
_cell_length_c                   9.5406(5)
_cell_measurement_reflns_used    3893
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      50.77
_cell_measurement_theta_min      3.53
_cell_volume                     2297.4(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      190(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0789
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17884
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.137
_diffrn_reflns_theta_min         2.718
_exptl_absorpt_coefficient_mu    0.515
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1197
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1283P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1819
_refine_ls_wR_factor_ref         0.2237
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2347
_reflns_number_total             4231
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc06186g2.cif
_cod_data_source_block           1_a
_cod_depositor_comments
'Adding full bibliography for 1560097--1560099.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1560097
_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   0.941
_shelx_estimated_absorpt_t_max   0.960
loop_
_space_group_symop_operation_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_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
B1 B 0.4490(2) 0.3602(2) 0.6383(4) 0.0504(9) Uani 1 1 d . . . . .
C1 C 0.8789(2) 0.1134(2) 0.7704(4) 0.0652(10) Uani 1 1 d . . . . .
H1A H 0.826117 0.077835 0.784161 0.098 Uiso 1 1 calc R U . . .
H1B H 0.934971 0.082641 0.751550 0.098 Uiso 1 1 calc R U . . .
H1C H 0.862072 0.148166 0.690534 0.098 Uiso 1 1 calc R U . . .
C2 C 0.9732(2) 0.2259(2) 0.8752(4) 0.0694(11) Uani 1 1 d . . . . .
H2A H 0.950191 0.257660 0.793981 0.104 Uiso 1 1 calc R U . . .
H2B H 1.033153 0.200981 0.856082 0.104 Uiso 1 1 calc R U . . .
H2C H 0.983032 0.259763 0.958170 0.104 Uiso 1 1 calc R U . . .
C3 C 0.9389(2) 0.1098(2) 1.0219(4) 0.0630(9) Uani 1 1 d . . . . .
H3A H 0.958184 0.142017 1.104267 0.095 Uiso 1 1 calc R U . . .
H3B H 0.993646 0.080673 0.992565 0.095 Uiso 1 1 calc R U . . .
H3C H 0.889836 0.072670 1.045982 0.095 Uiso 1 1 calc R U . . .
C4 C 0.9001(2) 0.16249(16) 0.9025(3) 0.0435(7) Uani 1 1 d . . . . .
C5 C 0.8124(2) 0.20559(16) 0.9463(3) 0.0428(7) Uani 1 1 d . . . . .
C6 C 0.8782(3) 0.5911(2) 0.9658(5) 0.0764(12) Uani 1 1 d . . . . .
C7 C 0.7608(2) 0.51480(18) 1.0218(4) 0.0579(9) Uani 1 1 d . . . . .
C8 C 0.8074(2) 0.47769(18) 0.9214(4) 0.0552(8) Uani 1 1 d . . . . .
C9 C 0.7842(2) 0.40463(17) 0.8720(3) 0.0497(8) Uani 1 1 d . . . . .
H9 H 0.817076 0.380092 0.800821 0.060 Uiso 1 1 calc R U . . .
C10 C 0.7091(2) 0.36790(17) 0.9323(3) 0.0440(7) Uani 1 1 d . . . . .
C11 C 0.6623(2) 0.40623(17) 1.0355(3) 0.0501(8) Uani 1 1 d . . . . .
H11 H 0.611656 0.379908 1.075364 0.060 Uiso 1 1 calc R U . . .
C12 C 0.6864(2) 0.48170(18) 1.0830(3) 0.0569(9) Uani 1 1 d . . . . .
H12 H 0.653598 0.507994 1.152378 0.068 Uiso 1 1 calc R U . . .
C13 C 0.6745(2) 0.28834(16) 0.8783(3) 0.0422(7) Uani 1 1 d . . . . .
H13 H 0.639595 0.262578 0.952979 0.051 Uiso 1 1 calc R U . . .
C14 C 0.6070(2) 0.29679(17) 0.7465(3) 0.0467(7) Uani 1 1 d . . . . .
H14A H 0.584584 0.243941 0.716307 0.056 Uiso 1 1 calc R U . . .
H14B H 0.642326 0.319031 0.670119 0.056 Uiso 1 1 calc R U . . .
C15 C 0.5212(2) 0.34889(18) 0.7664(3) 0.0521(8) Uani 1 1 d . . . . .
H15A H 0.544563 0.401405 0.797036 0.063 Uiso 1 1 calc R U . . .
H15B H 0.487195 0.326603 0.844039 0.063 Uiso 1 1 calc R U . . .
C16 C 0.3680(3) 0.3474(2) 0.4222(4) 0.0708(11) Uani 1 1 d . . . . .
C19 C 0.3232(3) 0.4132(2) 0.5085(4) 0.0667(10) Uani 1 1 d . . . . .
F1 F 0.87264(18) 0.65707(12) 0.8895(3) 0.0937(8) Uani 1 1 d . . . . .
F2 F 0.95860(17) 0.59601(13) 1.0463(3) 0.1034(9) Uani 1 1 d . . . . .
N1 N 0.75310(16) 0.23679(13) 0.8455(3) 0.0443(6) Uani 1 1 d . . . . .
H1 H 0.761359 0.226142 0.757043 0.053 Uiso 1 1 calc R U . . .
O1 O 0.45140(17) 0.32503(15) 0.5120(3) 0.0759(8) Uani 1 1 d . . . . .
O2 O 0.3742(2) 0.40829(17) 0.6425(3) 0.0898(10) Uani 1 1 d . . . . .
O3 O 0.79894(14) 0.21360(12) 1.0723(2) 0.0548(6) Uani 1 1 d . . . . .
O4 O 0.80323(19) 0.58795(13) 1.0492(3) 0.0740(8) Uani 1 1 d . . . . .
O5 O 0.87956(16) 0.52703(14) 0.8800(3) 0.0729(8) Uani 1 1 d . . . . .
C23 C 0.2199(3) 0.4028(4) 0.5270(7) 0.131(2) Uani 1 1 d . . . . .
H23A H 0.209316 0.351083 0.567907 0.196 Uiso 1 1 calc R U . . .
H23B H 0.183984 0.406911 0.435421 0.196 Uiso 1 1 calc R U . . .
H23C H 0.198950 0.443791 0.589800 0.196 Uiso 1 1 calc R U . . .
C21 C 0.3069(4) 0.2740(3) 0.4066(8) 0.134(2) Uani 1 1 d . . . . .
H21A H 0.345417 0.229742 0.378608 0.201 Uiso 1 1 calc R U . . .
H21B H 0.255008 0.282981 0.334538 0.201 Uiso 1 1 calc R U . . .
H21C H 0.280939 0.262128 0.496449 0.201 Uiso 1 1 calc R U . . .
C22 C 0.4019(5) 0.3733(5) 0.2849(6) 0.169(3) Uani 1 1 d . . . . .
H22A H 0.449358 0.414748 0.301470 0.253 Uiso 1 1 calc R U . . .
H22B H 0.348448 0.393482 0.224368 0.253 Uiso 1 1 calc R U . . .
H22C H 0.430156 0.328527 0.238850 0.253 Uiso 1 1 calc R U . . .
C20 C 0.3380(5) 0.4958(3) 0.4549(6) 0.129(2) Uani 1 1 d . . . . .
H20A H 0.324174 0.533830 0.527640 0.193 Uiso 1 1 calc R U . . .
H20B H 0.295645 0.504995 0.370464 0.193 Uiso 1 1 calc R U . . .
H20C H 0.403761 0.501979 0.431841 0.193 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 0.0137 0.0067 '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'
B B 0.0070 0.0029 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0583 0.0400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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
O2 B1 O1 111.7(3) . . ?
O2 B1 C15 122.0(3) . . ?
O1 B1 C15 126.3(3) . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C3 C4 C1 109.5(3) . . ?
C3 C4 C2 109.4(3) . . ?
C1 C4 C2 109.9(3) . . ?
C3 C4 C5 109.5(2) . . ?
C1 C4 C5 112.1(2) . . ?
C2 C4 C5 106.4(2) . . ?
O3 C5 N1 121.2(2) . . ?
O3 C5 C4 120.4(3) . . ?
N1 C5 C4 118.3(2) . . ?
F2 C6 F1 106.0(3) . . ?
F2 C6 O5 110.2(3) . . ?
F1 C6 O5 110.4(4) . . ?
F2 C6 O4 109.6(4) . . ?
F1 C6 O4 109.3(3) . . ?
O5 C6 O4 111.2(3) . . ?
C8 C7 C12 122.8(3) . . ?
C8 C7 O4 108.7(3) . . ?
C12 C7 O4 128.5(3) . . ?
C7 C8 C9 123.3(3) . . ?
C7 C8 O5 108.9(3) . . ?
C9 C8 O5 127.8(3) . . ?
C8 C9 C10 116.1(3) . . ?
C8 C9 H9 122.0 . . ?
C10 C9 H9 122.0 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 C13 120.0(2) . . ?
C9 C10 C13 119.8(2) . . ?
C10 C11 C12 122.8(3) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C7 C12 C11 114.8(3) . . ?
C7 C12 H12 122.6 . . ?
C11 C12 H12 122.6 . . ?
N1 C13 C10 112.0(2) . . ?
N1 C13 C14 108.6(2) . . ?
C10 C13 C14 111.2(2) . . ?
N1 C13 H13 108.3 . . ?
C10 C13 H13 108.3 . . ?
C14 C13 H13 108.3 . . ?
C13 C14 C15 114.0(2) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C14 C15 B1 117.4(3) . . ?
C14 C15 H15A 108.0 . . ?
B1 C15 H15A 108.0 . . ?
C14 C15 H15B 108.0 . . ?
B1 C15 H15B 108.0 . . ?
H15A C15 H15B 107.2 . . ?
O1 C16 C22 106.9(4) . . ?
O1 C16 C21 105.9(4) . . ?
C22 C16 C21 112.0(5) . . ?
O1 C16 C19 102.9(3) . . ?
C22 C16 C19 115.1(4) . . ?
C21 C16 C19 113.0(4) . . ?
O2 C19 C23 108.8(4) . . ?
O2 C19 C20 106.5(4) . . ?
C23 C19 C20 108.1(4) . . ?
O2 C19 C16 103.5(3) . . ?
C23 C19 C16 114.9(4) . . ?
C20 C19 C16 114.7(4) . . ?
C5 N1 C13 122.0(2) . . ?
C5 N1 H1 119.0 . . ?
C13 N1 H1 119.0 . . ?
B1 O1 C16 109.6(3) . . ?
B1 O2 C19 110.9(3) . . ?
C6 O4 C7 105.5(3) . . ?
C6 O5 C8 105.5(3) . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
B1 O2 1.344(4) . ?
B1 O1 1.348(4) . ?
B1 C15 1.545(5) . ?
C1 C4 1.523(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C4 1.533(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.520(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.530(4) . ?
C5 O3 1.239(3) . ?
C5 N1 1.338(4) . ?
C6 F2 1.328(5) . ?
C6 F1 1.337(4) . ?
C6 O5 1.365(5) . ?
C6 O4 1.377(5) . ?
C7 C8 1.361(4) . ?
C7 C12 1.366(5) . ?
C7 O4 1.399(4) . ?
C8 C9 1.362(4) . ?
C8 O5 1.403(4) . ?
C9 C10 1.396(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(4) . ?
C10 C13 1.517(4) . ?
C11 C12 1.396(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N1 1.471(3) . ?
C13 C14 1.528(4) . ?
C13 H13 1.0000 . ?
C14 C15 1.530(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 O1 1.457(4) . ?
C16 C22 1.496(7) . ?
C16 C21 1.521(6) . ?
C16 C19 1.554(5) . ?
C19 O2 1.422(4) . ?
C19 C23 1.500(6) . ?
C19 C20 1.517(6) . ?
N1 H1 0.8800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168307118
