#------------------------------------------------------------------------------
#$Date: 2022-04-19 01:11:11 +0300 (Tue, 19 Apr 2022) $
#$Revision: 274562 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/68/1566809.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_1566809
loop_
_publ_author_name
'Tang, Qi'
'Shi, Xiaodong'
'Richardson, David'
'Wojtas, Lukasz'
'Shan, Chuan'
'He, Ying'
'Lan, Yu'
'Yuan, Teng'
'Ye, Xiaohan'
'Li, Shi-Jun'
'Zhao, Kai'
_publ_section_title
;
 Design and Synthesis of Stable Four-Coordinated Benzotriazole-Borane with
 Tunable Fluorescence Emission
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC01103D
_journal_year                    2022
_chemical_formula_moiety         'C21 H15 B N4, C H2 Cl2'
_chemical_formula_sum            'C22 H17 B Cl2 N4'
_chemical_formula_weight         419.10
_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   mixed
_audit_creation_date             2021-07-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-03 deposited with the CCDC.	2022-04-18 downloaded from the CCDC.
;
_cell_angle_alpha                95.9950(10)
_cell_angle_beta                 100.5720(10)
_cell_angle_gamma                91.4500(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6707(2)
_cell_length_b                   8.6999(3)
_cell_length_c                   15.3408(5)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      79.61
_cell_measurement_theta_min      5.62
_cell_volume                     999.84(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON II CPAD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20096
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.024
_diffrn_reflns_theta_min         2.948
_diffrn_source                   'INCOATEC Imus micro-focus source'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.041
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0910 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.7930.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4231
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0335
_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)+(0.0442P)²+0.4426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3913
_reflns_number_total             4231
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc01103d2.cif
_cod_data_source_block           QT_167
_cod_database_code               1566809
_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   0.839
_shelx_estimated_absorpt_t_min   0.581
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26)
;
_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
N1 N 0.98104(15) 0.32688(15) 0.71340(8) 0.0248(3) Uani 1 1 d . . . . .
C2 C 0.85692(17) 0.36133(15) 0.66682(9) 0.0178(3) Uani 1 1 d . . . . .
B3 B 0.68320(19) 0.41285(17) 0.60422(10) 0.0170(3) Uani 1 1 d . . . . .
H3 H 0.713(2) 0.5343(18) 0.5882(10) 0.015(4) Uiso 1 1 d . . . . .
C4 C 0.50950(16) 0.40026(15) 0.65042(9) 0.0162(2) Uani 1 1 d . . . . .
C5 C 0.35907(16) 0.31537(15) 0.61205(9) 0.0174(3) Uani 1 1 d . . . . .
H5 H 0.260214 0.318736 0.641411 0.021 Uiso 1 1 calc R U . . .
C6 C 0.34456(16) 0.21932(15) 0.52729(9) 0.0167(2) Uani 1 1 d . . . . .
C7 C 0.49264(16) 0.21752(15) 0.48519(9) 0.0163(2) Uani 1 1 d . . . . .
N8 N 0.64789(13) 0.30120(12) 0.51455(7) 0.0158(2) Uani 1 1 d . . . . .
N9 N 0.75373(14) 0.28094(13) 0.45643(7) 0.0176(2) Uani 1 1 d . . . . .
N10 N 0.66554(14) 0.18255(13) 0.38858(7) 0.0165(2) Uani 1 1 d . . . . .
C11 C 0.49974(16) 0.13870(15) 0.40303(9) 0.0165(2) Uani 1 1 d . . . . .
C12 C 0.35204(17) 0.04784(15) 0.35471(9) 0.0189(3) Uani 1 1 d . . . . .
H12 H 0.353148 -0.008439 0.298321 0.023 Uiso 1 1 calc R U . . .
C13 C 0.20511(17) 0.04642(15) 0.39526(9) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.102302 -0.013531 0.365153 0.023 Uiso 1 1 calc R U . . .
C14 C 0.19944(17) 0.12958(15) 0.47938(9) 0.0188(3) Uani 1 1 d . . . . .
H14 H 0.094034 0.123621 0.503342 0.023 Uiso 1 1 calc R U . . .
C15 C 0.74376(16) 0.14833(16) 0.31103(8) 0.0174(3) Uani 1 1 d . . . . .
C16 C 0.84307(17) 0.26425(16) 0.28433(9) 0.0191(3) Uani 1 1 d . . . . .
H16 H 0.861437 0.363755 0.317393 0.023 Uiso 1 1 calc R U . . .
C17 C 0.91488(18) 0.23117(17) 0.20811(9) 0.0217(3) Uani 1 1 d . . . . .
H17 H 0.982843 0.308970 0.188509 0.026 Uiso 1 1 calc R U . . .
C18 C 0.88814(18) 0.08513(17) 0.16027(9) 0.0232(3) Uani 1 1 d . . . . .
H18 H 0.937641 0.063552 0.108142 0.028 Uiso 1 1 calc R U . . .
C19 C 0.78909(19) -0.02935(17) 0.18858(10) 0.0233(3) Uani 1 1 d . . . . .
H19 H 0.771198 -0.129055 0.155726 0.028 Uiso 1 1 calc R U . . .
C20 C 0.71598(18) 0.00132(16) 0.26479(9) 0.0206(3) Uani 1 1 d . . . . .
H20 H 0.648635 -0.076540 0.284701 0.025 Uiso 1 1 calc R U . . .
C21 C 0.51672(16) 0.49204(15) 0.73842(9) 0.0172(2) Uani 1 1 d . . . . .
C22 C 0.62728(17) 0.62622(15) 0.76331(9) 0.0193(3) Uani 1 1 d . . . . .
H22 H 0.701511 0.656260 0.724226 0.023 Uiso 1 1 calc R U . . .
C23 C 0.63043(18) 0.71608(16) 0.84397(10) 0.0233(3) Uani 1 1 d . . . . .
H23 H 0.704254 0.807904 0.858848 0.028 Uiso 1 1 calc R U . . .
C24 C 0.52583(19) 0.67208(18) 0.90303(10) 0.0254(3) Uani 1 1 d . . . . .
H24 H 0.527644 0.733463 0.958195 0.030 Uiso 1 1 calc R U . . .
C25 C 0.41870(18) 0.53741(18) 0.88049(9) 0.0243(3) Uani 1 1 d . . . . .
H25 H 0.348292 0.505839 0.920911 0.029 Uiso 1 1 calc R U . . .
C26 C 0.41372(17) 0.44876(16) 0.79950(9) 0.0205(3) Uani 1 1 d . . . . .
H26 H 0.339422 0.357182 0.785043 0.025 Uiso 1 1 calc R U . . .
C31 C 0.8338(2) 0.31170(18) 0.90534(10) 0.0276(3) Uani 1 1 d . . . . .
H31A H 0.773948 0.405284 0.924669 0.033 Uiso 1 1 calc R U . . .
H31B H 0.862098 0.323739 0.845931 0.033 Uiso 1 1 calc R U . . .
Cl32 Cl 0.68855(5) 0.14743(4) 0.89693(3) 0.03229(11) Uani 1 1 d . . . . .
Cl33 Cl 1.03312(4) 0.29562(4) 0.98225(2) 0.02709(10) Uani 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'
Cl Cl 0.3639 0.7018 '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
N1 C2 B3 178.37(14) . . ?
C2 B3 H3 107.1(8) . . ?
C2 B3 C4 111.49(10) . . ?
C4 B3 H3 113.3(8) . . ?
N8 B3 C2 108.55(11) . . ?
N8 B3 H3 108.4(8) . . ?
N8 B3 C4 107.87(10) . . ?
C5 C4 B3 123.80(12) . . ?
C5 C4 C21 119.05(11) . . ?
C21 C4 B3 117.12(11) . . ?
C4 C5 H5 119.0 . . ?
C4 C5 C6 121.99(12) . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 117.67(11) . . ?
C14 C6 C5 128.46(12) . . ?
C14 C6 C7 113.84(12) . . ?
N8 C7 C6 126.22(12) . . ?
N8 C7 C11 108.13(11) . . ?
C11 C7 C6 125.49(12) . . ?
C7 N8 B3 122.29(10) . . ?
N9 N8 B3 126.88(10) . . ?
N9 N8 C7 110.74(11) . . ?
N8 N9 N10 106.14(10) . . ?
N9 N10 C11 111.69(10) . . ?
N9 N10 C15 118.65(10) . . ?
C11 N10 C15 129.42(11) . . ?
C7 C11 N10 103.31(11) . . ?
C7 C11 C12 120.41(12) . . ?
N10 C11 C12 136.19(12) . . ?
C11 C12 H12 122.4 . . ?
C13 C12 C11 115.18(12) . . ?
C13 C12 H12 122.4 . . ?
C12 C13 H13 118.2 . . ?
C12 C13 C14 123.67(12) . . ?
C14 C13 H13 118.2 . . ?
C6 C14 C13 121.41(12) . . ?
C6 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 N10 118.75(12) . . ?
C20 C15 N10 118.98(11) . . ?
C20 C15 C16 122.26(12) . . ?
C15 C16 H16 120.8 . . ?
C15 C16 C17 118.36(13) . . ?
C17 C16 H16 120.8 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.52(13) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.09(13) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.33(13) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 C19 118.43(12) . . ?
C15 C20 H20 120.8 . . ?
C19 C20 H20 120.8 . . ?
C22 C21 C4 120.75(12) . . ?
C22 C21 C26 117.51(12) . . ?
C26 C21 C4 121.73(12) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.31(12) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.21(13) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.4 . . ?
C25 C24 C23 119.30(13) . . ?
C25 C24 H24 120.4 . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.52(13) . . ?
C26 C25 H25 119.7 . . ?
C21 C26 H26 119.4 . . ?
C25 C26 C21 121.12(13) . . ?
C25 C26 H26 119.4 . . ?
H31A C31 H31B 108.0 . . ?
Cl32 C31 H31A 109.3 . . ?
Cl32 C31 H31B 109.3 . . ?
Cl32 C31 Cl33 111.61(8) . . ?
Cl33 C31 H31A 109.3 . . ?
Cl33 C31 H31B 109.3 . . ?
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
N1 C2 1.1473(18) . ?
C2 B3 1.5968(19) . ?
B3 H3 1.137(16) . ?
B3 C4 1.6263(18) . ?
B3 N8 1.5748(18) . ?
C4 C5 1.3566(18) . ?
C4 C21 1.4861(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.4548(19) . ?
C6 C7 1.4055(17) . ?
C6 C14 1.3874(18) . ?
C7 N8 1.3572(16) . ?
C7 C11 1.3815(19) . ?
N8 N9 1.3134(15) . ?
N9 N10 1.3416(16) . ?
N10 C11 1.3816(16) . ?
N10 C15 1.4356(16) . ?
C11 C12 1.4078(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3841(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.421(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.3881(18) . ?
C15 C20 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3883(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.4020(18) . ?
C21 C26 1.4051(18) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.389(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.386(2) . ?
C26 H26 0.9500 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 Cl32 1.7689(15) . ?
C31 Cl33 1.7698(15) . ?
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
C2 B3 C4 C5 -123.52(13) . . . . ?
C2 B3 C4 C21 58.53(15) . . . . ?
C2 B3 N8 C7 122.84(12) . . . . ?
C2 B3 N8 N9 -61.01(15) . . . . ?
B3 C4 C5 C6 3.91(19) . . . . ?
B3 C4 C21 C22 25.36(17) . . . . ?
B3 C4 C21 C26 -154.83(12) . . . . ?
B3 N8 N9 N10 -176.59(11) . . . . ?
C4 B3 N8 C7 1.90(16) . . . . ?
C4 B3 N8 N9 178.05(11) . . . . ?
C4 C5 C6 C7 -0.41(18) . . . . ?
C4 C5 C6 C14 -178.47(13) . . . . ?
C4 C21 C22 C23 177.63(12) . . . . ?
C4 C21 C26 C25 -178.49(12) . . . . ?
C5 C4 C21 C22 -152.70(12) . . . . ?
C5 C4 C21 C26 27.11(18) . . . . ?
C5 C6 C7 N8 -2.28(19) . . . . ?
C5 C6 C7 C11 -177.02(12) . . . . ?
C5 C6 C14 C13 177.58(12) . . . . ?
C6 C7 N8 B3 1.22(19) . . . . ?
C6 C7 N8 N9 -175.49(12) . . . . ?
C6 C7 C11 N10 175.60(12) . . . . ?
C6 C7 C11 C12 -1.4(2) . . . . ?
C7 C6 C14 C13 -0.55(18) . . . . ?
C7 N8 N9 N10 -0.07(13) . . . . ?
C7 C11 C12 C13 0.58(18) . . . . ?
N8 B3 C4 C5 -4.43(17) . . . . ?
N8 B3 C4 C21 177.62(10) . . . . ?
N8 C7 C11 N10 0.06(13) . . . . ?
N8 C7 C11 C12 -176.93(11) . . . . ?
N8 N9 N10 C11 0.11(14) . . . . ?
N8 N9 N10 C15 175.02(10) . . . . ?
N9 N10 C11 C7 -0.10(14) . . . . ?
N9 N10 C11 C12 176.14(14) . . . . ?
N9 N10 C15 C16 -34.55(17) . . . . ?
N9 N10 C15 C20 146.16(12) . . . . ?
N10 C11 C12 C13 -175.18(14) . . . . ?
N10 C15 C16 C17 -178.57(11) . . . . ?
N10 C15 C20 C19 178.55(12) . . . . ?
C11 C7 N8 B3 176.72(11) . . . . ?
C11 C7 N8 N9 0.01(14) . . . . ?
C11 N10 C15 C16 139.32(13) . . . . ?
C11 N10 C15 C20 -39.97(19) . . . . ?
C11 C12 C13 C14 0.13(19) . . . . ?
C12 C13 C14 C6 -0.1(2) . . . . ?
C14 C6 C7 N8 176.06(12) . . . . ?
C14 C6 C7 C11 1.32(19) . . . . ?
C15 N10 C11 C7 -174.32(12) . . . . ?
C15 N10 C11 C12 1.9(2) . . . . ?
C15 C16 C17 C18 -0.3(2) . . . . ?
C16 C15 C20 C19 -0.7(2) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C18 C19 C20 0.1(2) . . . . ?
C18 C19 C20 C15 0.3(2) . . . . ?
C20 C15 C16 C17 0.69(19) . . . . ?
C21 C4 C5 C6 -178.17(11) . . . . ?
C21 C22 C23 C24 1.5(2) . . . . ?
C22 C21 C26 C25 1.33(19) . . . . ?
C22 C23 C24 C25 0.1(2) . . . . ?
C23 C24 C25 C26 -1.0(2) . . . . ?
C24 C25 C26 C21 0.2(2) . . . . ?
C26 C21 C22 C23 -2.19(19) . . . . ?
