Design and Synthesis of Stable Four-Coordinated Benzotriazole-Borane with Tunable Fluorescence Emission
Tang, Qi; Shi, Xiaodong; Richardson, David; Wojtas, Lukasz; Shan, Chuan; He, Ying; Lan, Yu; Yuan, Teng; Ye, Xiaohan; Li, Shi-Jun; Zhao, Kai; Chemical Science  (2022) –; doi:10.1039/D2SC01103D

data_1566815
_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         'C19 H13 B N4 S, C H Cl3'
_chemical_formula_sum            'C20 H14 B Cl3 N4 S'
_chemical_formula_weight         459.57
_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             2021-07-09
_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                102.614(2)
_cell_angle_beta                 92.073(2)
_cell_angle_gamma                115.981(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5849(6)
_cell_length_b                   9.6966(6)
_cell_length_c                   12.5042(7)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      79.77
_cell_measurement_theta_min      3.66
_cell_volume                     1007.91(11)
_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 0.967
_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  0.0294
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20495
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.354
_diffrn_reflns_theta_min         3.664
_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    5.205
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0644 before and 0.0467 after correction.
The Ratio of minimum to maximum transmission is 0.8361.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4261
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0259
_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/[\s^2^(Fo^2^)+(0.0270P)^2^+0.4754P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0663
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4074
_reflns_number_total             4261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc01103d2.cif
_cod_data_source_block           QT_N3_24
_cod_database_code               1566815
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.819
_shelx_estimated_absorpt_t_min   0.490
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 H32-H5
 -2.2 with sigma of 0.02
 C4-C31 \\sim C4-C21
 with sigma of 0.01
3. Restrained planarity
 C4, C31, C32, S33, C34, C35
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(S23) = Uanis(C34)
Uanis(C31) = Uanis(C21)
5. Rigid body (RIGU) restrains
 C21, C22, S23, C24, C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C31, C32, S33, C34, C35
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
6. Same fragment restrains
{C21, C22, S23, C24, C25} sigma for 1-2: 0.01, 1-3: 0.04
as in
{C31, C32, S33, C34, C35}
7. Others
 Sof(C31)=Sof(C32)=Sof(H32)=Sof(S33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=1-
 FVAR(1)
 Sof(C21)=Sof(C22)=Sof(H22)=Sof(S23)=Sof(C24)=Sof(H24)=Sof(C25)=Sof(H25)=FVAR(1)
8.a Ternary CH refined with riding coordinates:
 C41(H41)
8.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), C24(H24), C25(H25), C32(H32), C34(H34), C35(H35)
;
_shelx_res_checksum              19337
_shelx_hkl_checksum              86556
_olex2_submission_special_instructions 'No special instructions were received'