#------------------------------------------------------------------------------
#$Date: 2023-05-05 03:08:36 +0300 (Fri, 05 May 2023) $
#$Revision: 283033 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/11/7131122.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_7131122
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         'C16 H7 B F10 N O2'
_chemical_formula_sum            'C16 H7 B F10 N O2'
_chemical_formula_weight         446.04
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-01 deposited with the CCDC.	2022-12-15 downloaded from the CCDC.
;
_cell_angle_alpha                97.826(2)
_cell_angle_beta                 104.572(2)
_cell_angle_gamma                112.363(2)
_cell_formula_units_Z            2
_cell_length_a                   9.4139(2)
_cell_length_b                   9.7064(3)
_cell_length_c                   10.5352(3)
_cell_measurement_reflns_used    2796
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      69.852
_cell_measurement_theta_min      4.490
_cell_volume                     832.20(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200.0
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.981
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7603
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.059
_diffrn_reflns_theta_min         4.490
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.741
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0948 before and 0.0507 after correction. The Ratio of minimum to maximum transmission is 0.8346. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_description       block
_exptl_crystal_F_000             442
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0474
_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)+(0.0659P)²+0.1989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1337
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2380
_reflns_number_total             3107
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cc06207k2.cif
_cod_data_source_block           l2
_cod_depositor_comments
'Adding full bibliography for 7131121--7131128.cif.'
_cod_database_code               7131122
_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   0.818
_shelx_estimated_absorpt_t_min   0.722
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_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
F5 F 0.24536(19) -0.08983(17) 0.67983(18) 0.0508(4) Uani 1 1 d . . . . .
F10 F 0.76025(18) 0.36291(18) 0.52725(16) 0.0511(4) Uani 1 1 d . . . . .
F4 F -0.02172(19) -0.09421(19) 0.72812(18) 0.0545(4) Uani 1 1 d . . . . .
F1 F 0.34358(19) 0.38400(17) 0.56537(18) 0.0522(4) Uani 1 1 d . . . . .
F3 F -0.10728(19) 0.1389(2) 0.69855(19) 0.0587(5) Uani 1 1 d . . . . .
O2 O 0.44278(19) 0.18165(18) 0.44214(15) 0.0347(4) Uani 1 1 d . . . . .
O1 O 0.4239(2) 0.05001(18) 0.23873(16) 0.0383(4) Uani 1 1 d . . . . .
F9 F 1.0137(2) 0.61897(18) 0.6939(2) 0.0663(5) Uani 1 1 d . . . . .
F2 F 0.0781(2) 0.3784(2) 0.6175(2) 0.0669(5) Uani 1 1 d . . . . .
F6 F 0.5359(2) 0.2992(3) 0.87965(16) 0.0825(7) Uani 1 1 d . . . . .
N1 N 0.4926(2) -0.0238(2) 0.43095(18) 0.0321(4) Uani 1 1 d . . . . .
F8 F 1.0350(2) 0.7121(2) 0.9548(2) 0.0843(7) Uani 1 1 d . . . . .
F7 F 0.7934(3) 0.5522(3) 1.0442(2) 0.1015(9) Uani 1 1 d . . . . .
C1 C 0.4531(2) 0.0702(2) 0.3677(2) 0.0278(4) Uani 1 1 d . . . . .
C5 C 0.3076(3) 0.1483(2) 0.6215(2) 0.0316(5) Uani 1 1 d . . . . .
C10 C 0.2080(3) 0.0284(3) 0.6621(2) 0.0337(5) Uani 1 1 d . . . . .
C11 C 0.6331(3) 0.3209(2) 0.6939(2) 0.0335(5) Uani 1 1 d . . . . .
C6 C 0.2561(3) 0.2627(3) 0.6066(2) 0.0379(5) Uani 1 1 d . . . . .
C9 C 0.0698(3) 0.0236(3) 0.6878(2) 0.0384(5) Uani 1 1 d . . . . .
C16 C 0.7615(3) 0.4076(3) 0.6540(2) 0.0364(5) Uani 1 1 d . . . . .
C8 C 0.0255(3) 0.1418(3) 0.6733(2) 0.0410(6) Uani 1 1 d . . . . .
C2 C 0.3958(3) 0.1702(3) 0.1760(2) 0.0415(6) Uani 1 1 d . . . . .
H2 H 0.339019 0.215313 0.225077 0.050 Uiso 1 1 calc R . . . .
C7 C 0.1200(3) 0.2632(3) 0.6316(3) 0.0423(6) Uani 1 1 d . . . . .
C15 C 0.8946(3) 0.5389(3) 0.7387(3) 0.0452(6) Uani 1 1 d . . . . .
C12 C 0.6512(3) 0.3753(3) 0.8269(3) 0.0483(6) Uani 1 1 d . . . . .
C14 C 0.9049(3) 0.5863(3) 0.8692(3) 0.0563(8) Uani 1 1 d . . . . .
B1 B 0.4741(3) 0.1703(3) 0.5906(3) 0.0330(5) Uani 1 1 d . . . . .
C13 C 0.7826(4) 0.5052(4) 0.9154(3) 0.0604(8) Uani 1 1 d . . . . .
C3 C 0.5555(4) 0.2933(4) 0.1880(3) 0.0652(9) Uani 1 1 d . . . . .
H3A H 0.624803 0.333825 0.283614 0.098 Uiso 1 1 calc GR . . . .
H3B H 0.539087 0.376792 0.153430 0.098 Uiso 1 1 calc GR . . . .
H3C H 0.608137 0.250739 0.135051 0.098 Uiso 1 1 calc GR . . . .
C4 C 0.2857(4) 0.0859(4) 0.0330(3) 0.0702(10) Uani 1 1 d . . . . .
H4A H 0.340991 0.041287 -0.015093 0.105 Uiso 1 1 calc GR . . . .
H4B H 0.258273 0.157931 -0.013273 0.105 Uiso 1 1 calc GR . . . .
H4C H 0.185771 0.003330 0.034006 0.105 Uiso 1 1 calc GR . . . .
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'
F F 0.0727 0.0534 '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'
O O 0.0492 0.0322 '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 O2 B1 110.90(17) . . ?
C1 O1 C2 118.16(18) . . ?
N1 N1 B1 109.2(2) 2_656 2_656 ?
C1 N1 N1 107.7(2) . 2_656 ?
C1 N1 B1 143.11(19) . 2_656 ?
O2 C1 N1 116.01(18) . . ?
O1 C1 O2 122.70(19) . . ?
O1 C1 N1 121.27(19) . . ?
C10 C5 B1 128.4(2) . . ?
C6 C5 C10 114.5(2) . . ?
C6 C5 B1 117.1(2) . . ?
F5 C10 C5 120.0(2) . . ?
F5 C10 C9 116.8(2) . . ?
C9 C10 C5 123.2(2) . . ?
C16 C11 B1 122.7(2) . . ?
C12 C11 C16 114.0(2) . . ?
C12 C11 B1 123.3(2) . . ?
F1 C6 C5 119.2(2) . . ?
F1 C6 C7 116.4(2) . . ?
C7 C6 C5 124.3(2) . . ?
F4 C9 C10 120.9(2) . . ?
F4 C9 C8 119.3(2) . . ?
C8 C9 C10 119.8(2) . . ?
F10 C16 C11 119.5(2) . . ?
F10 C16 C15 117.0(2) . . ?
C15 C16 C11 123.5(2) . . ?
F3 C8 C9 120.4(2) . . ?
F3 C8 C7 120.5(2) . . ?
C9 C8 C7 119.1(2) . . ?
O1 C2 C4 105.2(2) . . ?
C3 C2 O1 108.7(2) . . ?
C3 C2 C4 114.6(2) . . ?
F2 C7 C6 121.5(2) . . ?
F2 C7 C8 119.5(2) . . ?
C6 C7 C8 119.0(2) . . ?
F9 C15 C16 120.8(3) . . ?
F9 C15 C14 119.8(2) . . ?
C14 C15 C16 119.4(3) . . ?
F6 C12 C11 120.0(2) . . ?
F6 C12 C13 115.6(2) . . ?
C11 C12 C13 124.5(3) . . ?
F8 C14 C15 120.6(3) . . ?
F8 C14 C13 119.4(3) . . ?
C15 C14 C13 120.0(2) . . ?
O2 B1 N1 96.16(17) . 2_656 ?
O2 B1 C5 105.58(18) . . ?
O2 B1 C11 111.39(18) . . ?
N1 B1 C5 116.72(19) 2_656 . ?
N1 B1 C11 112.23(19) 2_656 . ?
C5 B1 C11 113.17(19) . . ?
F7 C13 C12 121.6(3) . . ?
F7 C13 C14 119.8(3) . . ?
C14 C13 C12 118.6(3) . . ?
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
F5 C10 1.344(3) . ?
F10 C16 1.342(3) . ?
F4 C9 1.341(3) . ?
F1 C6 1.355(3) . ?
F3 C8 1.333(3) . ?
O2 C1 1.297(3) . ?
O2 B1 1.544(3) . ?
O1 C1 1.288(3) . ?
O1 C2 1.492(3) . ?
F9 C15 1.337(3) . ?
F2 C7 1.334(3) . ?
F6 C12 1.356(3) . ?
N1 N1 1.419(4) 2_656 ?
N1 C1 1.308(3) . ?
N1 B1 1.569(3) 2_656 ?
F8 C14 1.346(3) . ?
F7 C13 1.336(4) . ?
C5 C10 1.388(3) . ?
C5 C6 1.383(3) . ?
C5 B1 1.621(3) . ?
C10 C9 1.379(3) . ?
C11 C16 1.388(3) . ?
C11 C12 1.372(4) . ?
C11 B1 1.626(3) . ?
C6 C7 1.372(4) . ?
C9 C8 1.376(4) . ?
C16 C15 1.379(3) . ?
C8 C7 1.383(4) . ?
C2 C3 1.483(4) . ?
C2 C4 1.498(4) . ?
C15 C14 1.356(4) . ?
C12 C13 1.379(4) . ?
C14 C13 1.370(5) . ?
