#------------------------------------------------------------------------------
#$Date: 2023-05-05 03:08:36 +0300 (Fri, 05 May 2023) $
#$Revision: 283033 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/11/7131125.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_7131125
loop_
_publ_author_name
'Mandal, Dipendu'
'Hussain, Zahid'
'Luo, Yong-An'
'Wu, Yile'
'Stephan, Douglas W.'
_publ_section_title
;
 Transient hydroboration and hydroalumination of activated azo-species:
 avenues to NBO and NAlO-heterobicycles.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              780
_journal_page_last               783
_journal_paper_doi               10.1039/d2cc06207k
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C20 H7 B F10 N O2, 0.4(O)'
_chemical_formula_sum            'C20 H7 B F10 N O2.4'
_chemical_formula_weight         500.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-11-02
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-02 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                100.785(8)
_cell_angle_beta                 110.992(7)
_cell_angle_gamma                95.161(8)
_cell_formula_units_Z            2
_cell_length_a                   9.3567(11)
_cell_length_b                   9.9389(13)
_cell_length_c                   11.9720(14)
_cell_measurement_reflns_used    3505
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      24.21
_cell_measurement_theta_min      3.14
_cell_volume                     1006.0(2)
_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)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0805
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16370
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.436
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3527
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0582
_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)+(0.0599P)²+1.4029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1676
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2172
_reflns_number_total             3527
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc06207k2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7131121--7131128.cif.'
_cod_original_formula_sum        'C20 H7 B F10 N O2.40'
_cod_database_code               7131125
_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_max   0.982
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C26 \\sim F15: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
3. Others
 Fixed Sof: O3(0.4)
4.a Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B)
4.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C29(H29), C31(H31), C33(H33), C34(H34)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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 0.0980(3) 0.7435(2) 0.6899(2) 0.0306(6) Uani 1 1 d . . . . .
O2 O -0.0967(3) 0.6879(2) 0.5009(2) 0.0289(6) Uani 1 1 d . . . . .
F3 F 0.0493(3) 0.8014(2) 0.3774(2) 0.0497(7) Uani 1 1 d . . . . .
F4 F -0.3300(3) 0.4043(3) 0.1381(2) 0.0554(7) Uani 1 1 d . . . . .
F6 F 0.0897(3) 0.8404(3) 0.1765(2) 0.0543(7) Uani 1 1 d . . . . .
F7 F -0.3445(3) 0.2916(3) 0.3877(2) 0.0538(7) Uani 1 1 d . . . . .
C8 C 0.0196(4) 0.6586(4) 0.5848(3) 0.0234(8) Uani 1 1 d . . . . .
F9 F -0.3794(3) 0.7520(3) 0.3461(3) 0.0667(9) Uani 1 1 d . . . . .
C10 C -0.1438(4) 0.6014(4) 0.2681(3) 0.0254(8) Uani 1 1 d . . . . .
F11 F -0.0768(3) 0.6625(3) -0.0461(2) 0.0644(8) Uani 1 1 d . . . . .
F12 F -0.6443(3) 0.2472(3) 0.3509(2) 0.0748(10) Uani 1 1 d . . . . .
C14 C -0.3487(4) 0.5238(4) 0.3674(3) 0.0304(9) Uani 1 1 d . . . . .
F15 F -0.6794(3) 0.7071(4) 0.3150(3) 0.0920(12) Uani 1 1 d . U . . .
C16 C -0.0145(4) 0.7323(4) 0.1673(4) 0.0355(10) Uani 1 1 d . . . . .
C17 C -0.0379(4) 0.7095(4) 0.2703(3) 0.0306(9) Uani 1 1 d . . . . .
F18 F -0.2855(4) 0.4454(3) -0.0616(2) 0.0813(10) Uani 1 1 d . . . . .
C20 C 0.1657(5) 0.9618(4) 0.9407(4) 0.0424(10) Uani 1 1 d . . . . .
H20 H 0.085126 0.898877 0.943613 0.051 Uiso 1 1 calc R U . . .
C21 C -0.4418(4) 0.6252(5) 0.3482(4) 0.0460(12) Uani 1 1 d . . . . .
C22 C -0.2247(4) 0.5160(4) 0.1523(3) 0.0359(9) Uani 1 1 d . . . . .
C23 C -0.4227(4) 0.3989(5) 0.3685(3) 0.0386(10) Uani 1 1 d . . . . .
B24 B -0.1685(4) 0.5667(4) 0.3870(4) 0.0260(9) Uani 1 1 d . . . . .
C25 C 0.1721(4) 0.9693(4) 0.8280(3) 0.0333(9) Uani 1 1 d . . . . .
C26 C -0.5963(5) 0.6047(6) 0.3320(4) 0.0552(14) Uani 1 1 d . U . . .
C27 C 0.0531(5) 0.8826(4) 0.7118(4) 0.0431(10) Uani 1 1 d . . . . .
H27A H 0.046787 0.926226 0.642681 0.052 Uiso 1 1 calc R U . . .
H27B H -0.049957 0.873650 0.717923 0.052 Uiso 1 1 calc R U . . .
C28 C -0.2043(5) 0.5345(5) 0.0475(4) 0.0453(11) Uani 1 1 d . . . . .
C29 C 0.2918(5) 1.0607(4) 0.8257(4) 0.0407(10) Uani 1 1 d . . . . .
H29 H 0.298481 1.064703 0.749051 0.049 Uiso 1 1 calc R U . . .
C30 C -0.0984(5) 0.6435(5) 0.0554(4) 0.0421(11) Uani 1 1 d . . . . .
C31 C 0.2747(5) 1.0445(5) 1.0478(4) 0.0476(11) Uani 1 1 d . . . . .
H31 H 0.269156 1.038804 1.124542 0.057 Uiso 1 1 calc R U . . .
C32 C -0.5788(5) 0.3724(5) 0.3497(3) 0.0491(13) Uani 1 1 d . . . . .
C33 C 0.4007(5) 1.1457(4) 0.9324(4) 0.0456(11) Uani 1 1 d . . . . .
H33 H 0.480255 1.209719 0.929382 0.055 Uiso 1 1 calc R U . . .
C34 C 0.3931(5) 1.1366(5) 1.0447(4) 0.0498(12) Uani 1 1 d . . . . .
H34 H 0.468760 1.193326 1.119207 0.060 Uiso 1 1 calc R U . . .
C1 C -0.6648(4) 0.4781(6) 0.3321(4) 0.0558(14) Uani 1 1 d . . . . .
N2 N 0.0562(3) 0.5359(3) 0.5587(2) 0.0242(7) Uani 1 1 d . . . . .
F1 F -0.8153(2) 0.4544(4) 0.3154(2) 0.0844(11) Uani 1 1 d . . . . .
O3 O -0.3422(10) 0.9969(10) 0.5104(9) 0.091(3) Uani 0.4 1 d . . P . .
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'
F F 0.0171 0.0103 '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
C8 O1 C27 117.4(3) . . ?
C8 O2 B24 111.5(3) . . ?
O1 C8 N2 120.3(3) . . ?
O2 C8 O1 123.2(3) . . ?
O2 C8 N2 116.6(3) . . ?
C17 C10 B24 125.5(3) . . ?
C22 C10 C17 113.8(3) . . ?
C22 C10 B24 120.7(3) . . ?
C21 C14 B24 117.1(3) . . ?
C23 C14 C21 114.7(3) . . ?
C23 C14 B24 128.2(3) . . ?
F6 C16 C17 120.6(4) . . ?
F6 C16 C30 120.1(3) . . ?
C30 C16 C17 119.3(3) . . ?
F3 C17 C10 120.2(3) . . ?
F3 C17 C16 115.9(3) . . ?
C16 C17 C10 123.9(3) . . ?
C25 C20 H20 119.8 . . ?
C31 C20 H20 119.8 . . ?
C31 C20 C25 120.5(4) . . ?
F9 C21 C14 119.1(3) . . ?
F9 C21 C26 117.2(4) . . ?
C26 C21 C14 123.7(4) . . ?
F4 C22 C10 119.5(3) . . ?
F4 C22 C28 116.3(3) . . ?
C28 C22 C10 124.1(4) . . ?
F7 C23 C14 120.6(3) . . ?
F7 C23 C32 115.7(4) . . ?
C14 C23 C32 123.7(4) . . ?
O2 B24 C10 112.7(3) . . ?
O2 B24 C14 106.8(3) . . ?
O2 B24 N2 95.8(2) . 2_566 ?
C10 B24 C14 114.4(3) . . ?
N2 B24 C10 110.0(3) 2_566 . ?
N2 B24 C14 115.7(3) 2_566 . ?
C20 C25 C27 120.8(4) . . ?
C20 C25 C29 118.9(4) . . ?
C29 C25 C27 120.2(4) . . ?
F15 C26 C21 120.8(5) . . ?
F15 C26 C1 119.9(4) . . ?
C1 C26 C21 119.3(4) . . ?
O1 C27 H27A 110.1 . . ?
O1 C27 H27B 110.1 . . ?
C25 C27 O1 108.2(3) . . ?
C25 C27 H27A 110.1 . . ?
C25 C27 H27B 110.1 . . ?
H27A C27 H27B 108.4 . . ?
F18 C28 C22 120.7(4) . . ?
F18 C28 C30 119.9(3) . . ?
C30 C28 C22 119.5(4) . . ?
C25 C29 H29 119.4 . . ?
C33 C29 C25 121.2(4) . . ?
C33 C29 H29 119.4 . . ?
F11 C30 C16 120.5(4) . . ?
F11 C30 C28 120.1(4) . . ?
C28 C30 C16 119.4(3) . . ?
C20 C31 H31 119.9 . . ?
C20 C31 C34 120.3(4) . . ?
C34 C31 H31 119.9 . . ?
F12 C32 C23 120.6(5) . . ?
F12 C32 C1 120.6(4) . . ?
C1 C32 C23 118.7(4) . . ?
C29 C33 H33 120.4 . . ?
C29 C33 C34 119.2(4) . . ?
C34 C33 H33 120.4 . . ?
C31 C34 C33 119.9(4) . . ?
C31 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C26 C1 C32 119.9(4) . . ?
F1 C1 C26 120.8(5) . . ?
F1 C1 C32 119.4(5) . . ?
C8 N2 B24 143.8(3) . 2_566 ?
C8 N2 N2 107.1(3) . 2_566 ?
N2 N2 B24 108.8(3) 2_566 2_566 ?
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 C8 1.290(4) . ?
O1 C27 1.485(4) . ?
O2 C8 1.288(4) . ?
O2 B24 1.531(5) . ?
F3 C17 1.349(4) . ?
F4 C22 1.358(4) . ?
F6 C16 1.344(4) . ?
F7 C23 1.356(5) . ?
C8 N2 1.308(4) . ?
F9 C21 1.349(5) . ?
C10 C17 1.384(5) . ?
C10 C22 1.381(5) . ?
C10 B24 1.615(5) . ?
F11 C30 1.345(4) . ?
F12 C32 1.342(5) . ?
C14 C21 1.389(5) . ?
C14 C23 1.370(5) . ?
C14 B24 1.621(5) . ?
F15 C26 1.337(5) . ?
C16 C17 1.382(5) . ?
C16 C30 1.367(6) . ?
F18 C28 1.343(5) . ?
C20 H20 0.9500 . ?
C20 C25 1.387(5) . ?
C20 C31 1.371(6) . ?
C21 C26 1.379(6) . ?
C22 C28 1.378(5) . ?
C23 C32 1.389(5) . ?
B24 N2 1.586(5) 2_566 ?
C25 C27 1.479(5) . ?
C25 C29 1.389(5) . ?
C26 C1 1.360(7) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C30 1.365(6) . ?
C29 H29 0.9500 . ?
C29 C33 1.375(6) . ?
C31 H31 0.9500 . ?
C31 C34 1.388(6) . ?
C32 C1 1.382(7) . ?
C33 H33 0.9500 . ?
C33 C34 1.391(6) . ?
C34 H34 0.9500 . ?
C1 F1 1.341(4) . ?
N2 N2 1.422(5) 2_566 ?
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
O1 C8 N2 B24 3.9(6) . . . 2_566 ?
O1 C8 N2 N2 176.2(3) . . . 2_566 ?
O2 C8 N2 B24 -175.9(4) . . . 2_566 ?
O2 C8 N2 N2 -3.6(4) . . . 2_566 ?
F4 C22 C28 F18 0.0(6) . . . . ?
F4 C22 C28 C30 -178.9(4) . . . . ?
F6 C16 C17 F3 -0.1(5) . . . . ?
F6 C16 C17 C10 179.5(3) . . . . ?
F6 C16 C30 F11 0.6(6) . . . . ?
F6 C16 C30 C28 -179.7(3) . . . . ?
F7 C23 C32 F12 -0.1(5) . . . . ?
F7 C23 C32 C1 178.7(3) . . . . ?
C8 O1 C27 C25 -171.1(3) . . . . ?
C8 O2 B24 C10 -112.5(3) . . . . ?
C8 O2 B24 C14 121.1(3) . . . . ?
C8 O2 B24 N2 2.0(3) . . . 2_566 ?
F9 C21 C26 F15 0.0(6) . . . . ?
F9 C21 C26 C1 179.3(4) . . . . ?
C10 C22 C28 F18 178.8(4) . . . . ?
C10 C22 C28 C30 -0.2(6) . . . . ?
F12 C32 C1 C26 179.6(4) . . . . ?
F12 C32 C1 F1 -0.4(6) . . . . ?
C14 C21 C26 F15 179.4(4) . . . . ?
C14 C21 C26 C1 -1.3(6) . . . . ?
C14 C23 C32 F12 179.4(3) . . . . ?
C14 C23 C32 C1 -1.8(6) . . . . ?
F15 C26 C1 C32 -180.0(4) . . . . ?
F15 C26 C1 F1 0.0(6) . . . . ?
C17 C10 C22 F4 178.7(3) . . . . ?
C17 C10 C22 C28 0.0(6) . . . . ?
C17 C10 B24 O2 16.3(5) . . . . ?
C17 C10 B24 C14 138.5(4) . . . . ?
C17 C10 B24 N2 -89.3(4) . . . 2_566 ?
C17 C16 C30 F11 -179.4(3) . . . . ?
C17 C16 C30 C28 0.3(6) . . . . ?
F18 C28 C30 F11 0.8(6) . . . . ?
F18 C28 C30 C16 -178.9(4) . . . . ?
C20 C25 C27 O1 -83.7(4) . . . . ?
C20 C25 C29 C33 -1.6(6) . . . . ?
C20 C31 C34 C33 0.4(7) . . . . ?
C21 C14 C23 F7 -179.3(3) . . . . ?
C21 C14 C23 C32 1.2(5) . . . . ?
C21 C14 B24 O2 60.1(4) . . . . ?
C21 C14 B24 C10 -65.3(4) . . . . ?
C21 C14 B24 N2 165.3(3) . . . 2_566 ?
C21 C26 C1 C32 0.7(6) . . . . ?
C21 C26 C1 F1 -179.3(4) . . . . ?
C22 C10 C17 F3 179.9(3) . . . . ?
C22 C10 C17 C16 0.4(5) . . . . ?
C22 C10 B24 O2 -167.6(3) . . . . ?
C22 C10 B24 C14 -45.4(5) . . . . ?
C22 C10 B24 N2 86.8(4) . . . 2_566 ?
C22 C28 C30 F11 179.7(4) . . . . ?
C22 C28 C30 C16 0.0(6) . . . . ?
C23 C14 C21 F9 179.7(3) . . . . ?
C23 C14 C21 C26 0.4(6) . . . . ?
C23 C14 B24 O2 -119.2(4) . . . . ?
C23 C14 B24 C10 115.5(4) . . . . ?
C23 C14 B24 N2 -14.0(5) . . . 2_566 ?
C23 C32 C1 C26 0.8(6) . . . . ?
C23 C32 C1 F1 -179.2(3) . . . . ?
B24 O2 C8 O1 -179.0(3) . . . . ?
B24 O2 C8 N2 0.8(4) . . . . ?
B24 C10 C17 F3 -3.8(5) . . . . ?
B24 C10 C17 C16 176.7(3) . . . . ?
B24 C10 C22 F4 2.2(5) . . . . ?
B24 C10 C22 C28 -176.5(4) . . . . ?
B24 C14 C21 F9 0.4(5) . . . . ?
B24 C14 C21 C26 -179.0(4) . . . . ?
B24 C14 C23 F7 -0.1(6) . . . . ?
B24 C14 C23 C32 -179.5(3) . . . . ?
C25 C20 C31 C34 -0.2(7) . . . . ?
C25 C29 C33 C34 1.9(6) . . . . ?
C27 O1 C8 O2 -2.0(5) . . . . ?
C27 O1 C8 N2 178.2(3) . . . . ?
C27 C25 C29 C33 177.8(4) . . . . ?
C29 C25 C27 O1 96.9(4) . . . . ?
C29 C33 C34 C31 -1.2(6) . . . . ?
C30 C16 C17 F3 179.9(3) . . . . ?
C30 C16 C17 C10 -0.5(6) . . . . ?
C31 C20 C25 C27 -178.7(4) . . . . ?
C31 C20 C25 C29 0.8(6) . . . . ?
