#------------------------------------------------------------------------------
#$Date: 2024-04-05 01:21:18 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290795 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/10/1571021.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_1571021
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            'C14 H20 B N O2'
_chemical_formula_weight         245.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.7670(2)
_cell_length_b                   12.8036(5)
_cell_length_c                   18.9389(8)
_cell_measurement_reflns_used    59510
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.70
_cell_volume                     2610.85(16)
_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      150(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Nonius Kappa-CCD area-detector diffractometer'
_diffrn_measurement_method
'two φ and two ω scans with 2° steps (302 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  0.0177
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            59510
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         2.696
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2468
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0392
_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)+(0.0509P)²+0.6479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2140
_reflns_number_total             2468
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cy01702h3.cif
_cod_data_source_block           1a
_cod_depositor_comments
'Adding full bibliography for 1571020--1571024.cif.'
_cod_database_code               1571021
_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.21022(8) 0.21466(6) 0.58874(5) 0.0314(2) Uani 1 1 d . . . . .
O2 O 0.01755(8) 0.28478(7) 0.58795(5) 0.0380(2) Uani 1 1 d . . . . .
B1 B 0.28193(12) 0.31501(11) 0.60311(7) 0.0269(3) Uani 1 1 d . . . . .
N1 N 0.24775(9) 0.38712(8) 0.53482(5) 0.0274(2) Uani 1 1 d . . . . .
C1 C 0.08900(12) 0.21218(10) 0.58367(7) 0.0346(3) Uani 1 1 d . . . . .
H1 H 0.0529 0.1455 0.5757 0.042 Uiso 1 1 calc R U . . .
C2 C 0.25042(12) 0.36920(10) 0.67780(6) 0.0301(3) Uani 1 1 d . . . . .
H2 H 0.1618 0.3925 0.6774 0.036 Uiso 1 1 calc R U . . .
C3 C 0.26617(12) 0.28337(10) 0.73466(7) 0.0364(3) Uani 1 1 d . . . . .
H3A H 0.2492 0.3144 0.7816 0.044 Uiso 1 1 calc R U . . .
H3B H 0.2032 0.2284 0.7263 0.044 Uiso 1 1 calc R U . . .
C4 C 0.39515(13) 0.23231(11) 0.73630(7) 0.0388(3) Uani 1 1 d . . . . .
H4A H 0.3902 0.1676 0.7647 0.047 Uiso 1 1 calc R U . . .
H4B H 0.4534 0.2802 0.7605 0.047 Uiso 1 1 calc R U . . .
C5 C 0.44865(12) 0.20506(10) 0.66338(7) 0.0345(3) Uani 1 1 d . . . . .
H5A H 0.4122 0.1378 0.6480 0.041 Uiso 1 1 calc R U . . .
H5B H 0.5393 0.1943 0.6685 0.041 Uiso 1 1 calc R U . . .
C6 C 0.42713(11) 0.28613(10) 0.60425(6) 0.0304(3) Uani 1 1 d . . . . .
H6 H 0.4491 0.2531 0.5580 0.036 Uiso 1 1 calc R U . . .
C7 C 0.50498(12) 0.38602(11) 0.61284(7) 0.0390(3) Uani 1 1 d . . . . .
H7A H 0.5940 0.3666 0.6141 0.047 Uiso 1 1 calc R U . . .
H7B H 0.4919 0.4310 0.5710 0.047 Uiso 1 1 calc R U . . .
C8 C 0.47420(13) 0.44888(11) 0.67917(8) 0.0427(3) Uani 1 1 d . . . . .
H8A H 0.5147 0.5181 0.6757 0.051 Uiso 1 1 calc R U . . .
H8B H 0.5098 0.4126 0.7206 0.051 Uiso 1 1 calc R U . . .
C9 C 0.33448(13) 0.46507(10) 0.69165(7) 0.0377(3) Uani 1 1 d . . . . .
H9A H 0.3060 0.5230 0.6610 0.045 Uiso 1 1 calc R U . . .
H9B H 0.3224 0.4874 0.7412 0.045 Uiso 1 1 calc R U . . .
C10 C 0.28120(11) 0.35379(11) 0.46986(6) 0.0337(3) Uani 1 1 d . . . . .
H10 H 0.3288 0.2916 0.4656 0.040 Uiso 1 1 calc R U . . .
C11 C 0.24828(13) 0.40724(12) 0.40965(7) 0.0403(3) Uani 1 1 d . . . . .
H11 H 0.2719 0.3816 0.3645 0.048 Uiso 1 1 calc R U . . .
C12 C 0.18048(13) 0.49866(11) 0.41545(7) 0.0409(3) Uani 1 1 d . . . . .
H12 H 0.1576 0.5370 0.3745 0.049 Uiso 1 1 calc R U . . .
C13 C 0.14692(13) 0.53288(11) 0.48152(7) 0.0386(3) Uani 1 1 d . . . . .
H13 H 0.1009 0.5957 0.4870 0.046 Uiso 1 1 calc R U . . .
C14 C 0.18084(12) 0.47503(9) 0.53983(7) 0.0332(3) Uani 1 1 d . . . . .
H14 H 0.1558 0.4984 0.5853 0.040 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 122.61(10) . . ?
O1 B1 C6 107.54(10) . . ?
O1 B1 C2 114.40(10) . . ?
C6 B1 C2 106.98(10) . . ?
O1 B1 N1 102.79(9) . . ?
C6 B1 N1 111.13(10) . . ?
C2 B1 N1 113.88(10) . . ?
C14 N1 C10 118.25(10) . . ?
C14 N1 B1 122.73(10) . . ?
C10 N1 B1 118.89(10) . . ?
O2 C1 O1 127.64(12) . . ?
O2 C1 H1 116.2 . . ?
O1 C1 H1 116.2 . . ?
C9 C2 C3 112.40(10) . . ?
C9 C2 B1 111.54(10) . . ?
C3 C2 B1 106.38(10) . . ?
C9 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
B1 C2 H2 108.8 . . ?
C4 C3 C2 114.55(10) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 114.68(10) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 116.29(10) . . ?
C4 C5 H5A 108.2 . . ?
C6 C5 H5A 108.2 . . ?
C4 C5 H5B 108.2 . . ?
C6 C5 H5B 108.2 . . ?
H5A C5 H5B 107.4 . . ?
C7 C6 C5 113.61(10) . . ?
C7 C6 B1 109.90(10) . . ?
C5 C6 B1 108.08(10) . . ?
C7 C6 H6 108.4 . . ?
C5 C6 H6 108.4 . . ?
B1 C6 H6 108.4 . . ?
C8 C7 C6 114.00(11) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C9 114.19(11) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C2 116.07(11) . . ?
C8 C9 H9A 108.3 . . ?
C2 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
C2 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
N1 C10 C11 121.92(12) . . ?
N1 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 119.38(12) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 118.73(12) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 119.23(13) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N1 C14 C13 122.48(12) . . ?
N1 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
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 1.3091(16) . ?
O1 B1 1.5235(16) . ?
O2 C1 1.2093(16) . ?
B1 C6 1.6067(18) . ?
B1 C2 1.6116(17) . ?
B1 N1 1.6311(16) . ?
N1 C14 1.3397(16) . ?
N1 C10 1.3511(15) . ?
C1 H1 0.9500 . ?
C2 C9 1.5476(18) . ?
C2 C3 1.5479(17) . ?
C2 H2 1.0000 . ?
C3 C4 1.5352(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5365(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5443(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5377(17) . ?
C6 H6 1.0000 . ?
C7 C8 1.528(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.537(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.3764(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3789(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
