#------------------------------------------------------------------------------
#$Date: 2024-09-06 02:58:27 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294495 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/22/1572201.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_1572201
loop_
_publ_author_name
'Fan, Zi-Heng'
'Kang, Jia-Xin'
'Jia, Sihan'
'Pan, Qiao-Jing'
'Cao, Lei'
'Chen, Xi-Meng'
'Xu, Cong-Qiao'
'Ma, Yan-Na'
'Chen, Xuenian'
_publ_section_title
;
 Triborane (B₃H₇)-mediated regioselective
 substitution reactions of pyridine derivatives.
;
_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              13923
_journal_page_last               13929
_journal_paper_doi               10.1039/d4sc03109a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C5 H12 B3 N'
_chemical_formula_sum            'C5 H12 B3 N'
_chemical_formula_weight         118.59
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-10
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-11-15 deposited with the CCDC.	2024-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9099(8)
_cell_length_b                   8.0101(4)
_cell_length_c                   14.4607(8)
_cell_measurement_reflns_used    1906
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6820
_cell_measurement_theta_min      6.3670
_cell_volume                     1611.21(15)
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -44.00   1.00    1.51    --  -35.62 -57.00 -42.00   58
  2  ω      4.00  33.00   1.00    1.51    --   35.62 -96.00  87.00   29
  3  ω      4.00  45.00   1.00    1.51    --   35.62 -73.00-177.00   41
  4  ω    110.00 168.00   1.00    6.03    --  106.81  73.00 -48.00   58
  5  ω    111.00 165.00   1.00    6.03    --  106.81  57.00  98.00   54
  6  ω     40.00 104.00   1.00    6.03    --  106.81 -57.00 -42.00   64
  7  ω     41.00 101.00   1.00    6.03    --  106.81 -96.00  87.00   60
  8  ω     64.00  94.00   1.00    1.51    --   35.62 178.00   0.00   30
  9  ω     58.00 108.00   1.00    1.51    --   35.62-178.00-150.00   50
 10  ω     66.00 105.00   1.00    1.51    --   35.62 178.00  90.00   39
 11  ω    108.00 157.00   1.00    6.03    --  106.81  77.00  60.00   49
 12  ω     53.00 105.00   1.00    6.03    --  106.81-111.00-150.00   52
 13  ω    127.00 173.00   1.00    6.03    --  106.81 111.00 -90.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0672201000
_diffrn_orient_matrix_UB_12      -0.1410068000
_diffrn_orient_matrix_UB_13      0.0327000000
_diffrn_orient_matrix_UB_21      0.0349498000
_diffrn_orient_matrix_UB_22      0.1106990000
_diffrn_orient_matrix_UB_23      0.0805265000
_diffrn_orient_matrix_UB_31      -0.0809223000
_diffrn_orient_matrix_UB_32      -0.0689226000
_diffrn_orient_matrix_UB_33      0.0617386000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0182
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4012
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.205
_diffrn_reflns_theta_min         6.121
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    0.978
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0546
_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)+(0.0724P)²+0.3844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1744
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1154
_reflns_number_total             1486
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4sc03109a2.cif
_cod_data_source_block           20231010-fzh_auto
_cod_depositor_comments
'Adding full bibliography for 1572200--1572201.cif.'
_cod_database_code               1572201
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C1 N1 B1 H1'
_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_max   0.996
_shelx_estimated_absorpt_t_min   0.996
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C3(H3), C4(H4)
;
_smtbx_masks_void_probe_radius   0.5
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.257
_oxdiff_exptl_absorpt_empirical_full_min 0.667
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
N1 N 0.31253(10) 0.70380(18) 0.58800(9) 0.0504(4) Uani 1 1 d . . . . .
C2 C 0.33097(15) 0.6509(3) 0.50245(13) 0.0650(6) Uani 1 1 d . . . . .
H2 H 0.394621 0.644974 0.483038 0.078 Uiso 1 1 calc R U . . .
C6 C 0.22028(13) 0.7152(3) 0.61416(15) 0.0613(5) Uani 1 1 d . . . . .
H6 H 0.206066 0.753158 0.673379 0.074 Uiso 1 1 calc R U . . .
C5 C 0.14639(16) 0.6725(3) 0.55623(18) 0.0764(7) Uani 1 1 d . . . . .
H5 H 0.082975 0.681551 0.575995 0.092 Uiso 1 1 calc R U . . .
C3 C 0.26009(19) 0.6049(3) 0.44206(15) 0.0786(7) Uani 1 1 d . . . . .
H3 H 0.275546 0.566301 0.383265 0.094 Uiso 1 1 calc R U . . .
C4 C 0.16664(18) 0.6165(3) 0.46916(17) 0.0802(7) Uani 1 1 d . . . . .
H4 H 0.117312 0.586799 0.428995 0.096 Uiso 1 1 calc R U . . .
B7 B 0.39616(16) 0.7573(3) 0.65596(16) 0.0583(6) Uani 1 1 d . . . . .
B9 B 0.4899(2) 0.5994(4) 0.6703(2) 0.0746(8) Uani 1 1 d . . . . .
B8 B 0.4051(2) 0.6153(4) 0.75523(18) 0.0718(7) Uani 1 1 d . . . . .
H7A H 0.4546(16) 0.820(3) 0.6119(15) 0.071(6) Uiso 1 1 d . . . . .
H8A H 0.3328(18) 0.549(3) 0.7573(18) 0.095(8) Uiso 1 1 d . . . . .
H8B H 0.4248(18) 0.682(3) 0.8212(17) 0.091(7) Uiso 1 1 d . . . . .
H9A H 0.565(2) 0.645(3) 0.6843(17) 0.107(9) Uiso 1 1 d . . . . .
H9B H 0.4832(17) 0.521(3) 0.6095(18) 0.087(7) Uiso 1 1 d . . . . .
H9C H 0.465(2) 0.509(4) 0.7376(19) 0.106(9) Uiso 1 1 d . . . . .
H7B H 0.3710(19) 0.853(3) 0.7006(17) 0.097(8) Uiso 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 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C2 N1 C6 117.89(17) . . ?
C2 N1 B7 121.42(16) . . ?
C6 N1 B7 120.66(16) . . ?
N1 C2 H2 118.7 . . ?
N1 C2 C3 122.7(2) . . ?
C3 C2 H2 118.7 . . ?
N1 C6 H6 119.0 . . ?
N1 C6 C5 121.9(2) . . ?
C5 C6 H6 119.0 . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.4(2) . . ?
C4 C5 H5 120.3 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3 120.4 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
N1 B7 B9 114.02(18) . . ?
N1 B7 B8 111.56(16) . . ?
N1 B7 H7A 107.1(11) . . ?
N1 B7 H7B 109.3(15) . . ?
B9 B7 B8 55.58(14) . . ?
B9 B7 H7A 81.9(11) . . ?
B9 B7 H7B 131.8(14) . . ?
B8 B7 H7A 131.0(11) . . ?
B8 B7 H7B 89.6(14) . . ?
H7A B7 H7B 104.9(17) . . ?
B7 B9 H9A 117.1(14) . . ?
B7 B9 H9B 104.4(13) . . ?
B7 B9 H9C 106.6(14) . . ?
B8 B9 B7 62.44(15) . . ?
B8 B9 H9A 119.0(14) . . ?
B8 B9 H9B 124.6(13) . . ?
B8 B9 H9C 45.3(13) . . ?
H9A B9 H9B 114.6(19) . . ?
H9A B9 H9C 107.8(18) . . ?
H9B B9 H9C 105.6(18) . . ?
B7 B8 H8A 104.4(13) . . ?
B7 B8 H8B 112.5(12) . . ?
B7 B8 H9C 108.4(13) . . ?
B9 B8 B7 61.98(14) . . ?
B9 B8 H8A 126.5(13) . . ?
B9 B8 H8B 118.4(13) . . ?
B9 B8 H9C 47.6(13) . . ?
H8A B8 H8B 114.5(18) . . ?
H8A B8 H9C 106.4(19) . . ?
H8B B8 H9C 110.2(18) . . ?
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
N1 C2 1.333(2) . ?
N1 C6 1.341(2) . ?
N1 B7 1.582(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.369(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.366(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.361(4) . ?
C4 H4 0.9300 . ?
B7 B9 1.828(3) . ?
B7 B8 1.836(3) . ?
B7 H7A 1.15(2) . ?
B7 H7B 1.06(3) . ?
B9 B8 1.708(4) . ?
B9 H9A 1.12(3) . ?
B9 H9B 1.08(3) . ?
B9 H9C 1.26(3) . ?
B8 H8A 1.14(3) . ?
B8 H8B 1.13(2) . ?
B8 H9C 1.21(3) . ?
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
N1 C2 C3 C4 1.4(4) . . . . ?
N1 C6 C5 C4 0.0(3) . . . . ?
N1 B7 B9 B8 -100.5(2) . . . . ?
N1 B7 B8 B9 105.1(2) . . . . ?
C2 N1 C6 C5 0.8(3) . . . . ?
C2 N1 B7 B9 -53.4(2) . . . . ?
C2 N1 B7 B8 -114.1(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C6 N1 C2 C3 -1.5(3) . . . . ?
C6 N1 B7 B9 128.6(2) . . . . ?
C6 N1 B7 B8 67.9(2) . . . . ?
C6 C5 C4 C3 -0.1(4) . . . . ?
B7 N1 C2 C3 -179.6(2) . . . . ?
B7 N1 C6 C5 178.85(19) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.496 -0.804 -0.673 483.0 9.1 ?
2 0.125 0.000 0.125 0.0 0.0 ?
3 0.125 0.500 0.625 0.0 0.0 ?
4 0.375 0.000 0.625 0.0 0.0 ?
5 0.375 0.500 0.125 0.0 0.0 ?
6 0.625 0.000 0.375 0.0 0.0 ?
7 0.625 0.500 0.875 0.0 0.0 ?
8 0.875 0.000 0.875 0.0 0.0 ?
9 0.875 0.500 0.375 0.0 0.0 ?
