#------------------------------------------------------------------------------
#$Date: 2024-04-05 01:21:18 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290795 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/10/1571022.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_1571022
loop_
_publ_author_name
'Durin, Gabriel'
'Romero, R. Martin'
'Godou, Timothé'
'Chauvier, Clément'
'Thuéry, Pierre'
'Nicolas, Emmanuel'
'Cantat, Thibault'
_publ_section_title
;
 Formoxyboranes as hydroborane surrogates for the catalytic reduction of
 carbonyls through transfer hydroboration
;
_journal_issue                   7
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              1848
_journal_page_last               1853
_journal_paper_doi               10.1039/D3CY01702H
_journal_volume                  14
_journal_year                    2024
_chemical_formula_sum            'C16 H25 B N2 O2'
_chemical_formula_weight         288.19
_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
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2023-07-25 deposited with the CCDC.	2024-02-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.551(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8725(5)
_cell_length_b                   7.3758(4)
_cell_length_c                   21.8820(12)
_cell_measurement_reflns_used    70088
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.92
_cell_volume                     1575.68(15)
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method
'two φ and nine ω scans with 2° steps (625 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  0.0222
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            70088
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_min         2.918
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0367
_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)+(0.0549P)²+0.3088P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2550
_reflns_number_total             2965
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cy01702h3.cif
_cod_data_source_block           1b
_cod_depositor_comments
'Adding full bibliography for 1571020--1571024.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1571022
_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.
;
_shelxl_version_number           2014-3
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
O1 O 0.91841(8) 0.04291(12) 0.56420(4) 0.0267(2) Uani 1 1 d . . . . .
O2 O 0.72479(8) -0.11148(12) 0.52927(4) 0.0284(2) Uani 1 1 d . . . . .
N1 N 0.75223(9) 0.22065(14) 0.61583(4) 0.0224(2) Uani 1 1 d . . . . .
N2 N 0.40321(10) 0.54531(14) 0.57353(5) 0.0255(2) Uani 1 1 d . . . . .
B1 B 0.88720(13) 0.09525(19) 0.62849(6) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.83833(12) -0.05541(18) 0.52457(5) 0.0276(3) Uani 1 1 d . . . . .
H1 H 0.8729 -0.0868 0.4877 0.033 Uiso 1 1 calc R U . . .
C2 C 1.01921(11) 0.20640(17) 0.66115(5) 0.0236(3) Uani 1 1 d . . . . .
H2 H 1.0336 0.3122 0.6343 0.028 Uiso 1 1 calc R U . . .
C3 C 1.14673(11) 0.08198(18) 0.66532(6) 0.0269(3) Uani 1 1 d . . . . .
H3A H 1.1689 0.0640 0.6231 0.032 Uiso 1 1 calc R U . . .
H3B H 1.2252 0.1457 0.6895 0.032 Uiso 1 1 calc R U . . .
C4 C 1.13287(12) -0.10531(18) 0.69461(6) 0.0299(3) Uani 1 1 d . . . . .
H4A H 1.2067 -0.1848 0.6840 0.036 Uiso 1 1 calc R U . . .
H4B H 1.1466 -0.0915 0.7401 0.036 Uiso 1 1 calc R U . . .
C5 C 0.99462(12) -0.19923(18) 0.67438(6) 0.0302(3) Uani 1 1 d . . . . .
H5A H 0.9857 -0.3011 0.7030 0.036 Uiso 1 1 calc R U . . .
H5B H 0.9945 -0.2510 0.6326 0.036 Uiso 1 1 calc R U . . .
C6 C 0.86849(12) -0.07436(17) 0.67284(5) 0.0245(3) Uani 1 1 d . . . . .
H6 H 0.7851 -0.1436 0.6546 0.029 Uiso 1 1 calc R U . . .
C7 C 0.84689(12) -0.00522(18) 0.73748(5) 0.0276(3) Uani 1 1 d . . . . .
H7A H 0.7548 0.0504 0.7339 0.033 Uiso 1 1 calc R U . . .
H7B H 0.8477 -0.1110 0.7654 0.033 Uiso 1 1 calc R U . . .
C8 C 0.95245(13) 0.13338(18) 0.76796(5) 0.0289(3) Uani 1 1 d . . . . .
H8A H 0.9149 0.1934 0.8023 0.035 Uiso 1 1 calc R U . . .
H8B H 1.0363 0.0676 0.7860 0.035 Uiso 1 1 calc R U . . .
C9 C 0.99180(12) 0.27955(18) 0.72400(5) 0.0265(3) Uani 1 1 d . . . . .
H9A H 1.0750 0.3427 0.7443 0.032 Uiso 1 1 calc R U . . .
H9B H 0.9170 0.3700 0.7168 0.032 Uiso 1 1 calc R U . . .
C10 C 0.76013(12) 0.39539(17) 0.59806(5) 0.0244(3) Uani 1 1 d . . . . .
H10 H 0.8482 0.4438 0.5953 0.029 Uiso 1 1 calc R U . . .
C11 C 0.64936(12) 0.50657(17) 0.58378(5) 0.0248(3) Uani 1 1 d . . . . .
H11 H 0.6617 0.6283 0.5716 0.030 Uiso 1 1 calc R U . . .
C12 C 0.51611(12) 0.44040(17) 0.58715(5) 0.0232(3) Uani 1 1 d . . . . .
C13 C 0.50850(12) 0.25773(17) 0.60562(5) 0.0245(3) Uani 1 1 d . . . . .
H13 H 0.4220 0.2051 0.6089 0.029 Uiso 1 1 calc R U . . .
C14 C 0.62513(11) 0.15606(17) 0.61888(5) 0.0240(3) Uani 1 1 d . . . . .
H14 H 0.6164 0.0334 0.6309 0.029 Uiso 1 1 calc R U . . .
C15 C 0.41075(12) 0.73817(18) 0.56030(6) 0.0293(3) Uani 1 1 d . . . . .
H15A H 0.4142 0.8072 0.5988 0.044 Uiso 1 1 calc R U . . .
H15B H 0.3297 0.7743 0.5314 0.044 Uiso 1 1 calc R U . . .
H15C H 0.4934 0.7628 0.5418 0.044 Uiso 1 1 calc R U . . .
C16 C 0.26917(12) 0.47510(19) 0.58180(6) 0.0317(3) Uani 1 1 d . . . . .
H16A H 0.2513 0.3622 0.5584 0.048 Uiso 1 1 calc R U . . .
H16B H 0.1986 0.5646 0.5669 0.048 Uiso 1 1 calc R U . . .
H16C H 0.2675 0.4513 0.6257 0.048 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'
B B 0.0013 0.0007 '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
C1 O1 B1 124.45(9) . . ?
C10 N1 C14 116.32(10) . . ?
C10 N1 B1 120.99(9) . . ?
C14 N1 B1 122.59(10) . . ?
C12 N2 C15 122.53(10) . . ?
C12 N2 C16 120.19(11) . . ?
C15 N2 C16 116.50(10) . . ?
O1 B1 C6 114.45(10) . . ?
O1 B1 N1 105.10(9) . . ?
C6 B1 N1 112.53(9) . . ?
O1 B1 C2 105.96(9) . . ?
C6 B1 C2 106.56(9) . . ?
N1 B1 C2 112.16(10) . . ?
O2 C1 O1 127.57(11) . . ?
O2 C1 H1 116.2 . . ?
O1 C1 H1 116.2 . . ?
C9 C2 C3 113.86(9) . . ?
C9 C2 B1 109.65(9) . . ?
C3 C2 B1 108.71(10) . . ?
C9 C2 H2 108.2 . . ?
C3 C2 H2 108.2 . . ?
B1 C2 H2 108.2 . . ?
C4 C3 C2 115.77(10) . . ?
C4 C3 H3A 108.3 . . ?
C2 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
C2 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C5 C4 C3 114.55(10) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 114.59(11) . . ?
C4 C5 H5A 108.6 . . ?
C6 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
C6 C5 H5B 108.6 . . ?
H5A C5 H5B 107.6 . . ?
C5 C6 C7 113.36(10) . . ?
C5 C6 B1 108.17(10) . . ?
C7 C6 B1 109.78(10) . . ?
C5 C6 H6 108.5 . . ?
C7 C6 H6 108.5 . . ?
B1 C6 H6 108.5 . . ?
C8 C7 C6 116.00(10) . . ?
C8 C7 H7A 108.3 . . ?
C6 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C9 C8 C7 114.43(10) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C2 114.14(11) . . ?
C8 C9 H9A 108.7 . . ?
C2 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C2 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N1 C10 C11 124.05(11) . . ?
N1 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
C10 C11 C12 120.00(11) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N2 C12 C13 122.12(11) . . ?
N2 C12 C11 122.20(11) . . ?
C13 C12 C11 115.68(11) . . ?
C14 C13 C12 120.31(11) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
N1 C14 C13 123.63(11) . . ?
N1 C14 H14 118.2 . . ?
C13 C14 H14 118.2 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O1 C1 1.3035(15) . ?
O1 B1 1.5336(15) . ?
O2 C1 1.2134(15) . ?
N1 C10 1.3519(16) . ?
N1 C14 1.3530(15) . ?
N1 B1 1.6119(16) . ?
N2 C12 1.3532(15) . ?
N2 C15 1.4558(17) . ?
N2 C16 1.4571(16) . ?
B1 C6 1.6107(18) . ?
B1 C2 1.6138(17) . ?
C1 H1 0.9500 . ?
C2 C9 1.5382(16) . ?
C2 C3 1.5496(16) . ?
C2 H2 1.0000 . ?
C3 C4 1.5375(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5359(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5452(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5478(17) . ?
C6 H6 1.0000 . ?
C7 C8 1.5393(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5329(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3654(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.4153(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.4119(18) . ?
C13 C14 1.3686(17) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
