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#$Date: 2024-01-06 09:19:12 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/00/1570067.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_1570067
loop_
_publ_author_name
'Adamek, Jan'
'Marek-Urban, Paulina H'
'Woźniak, Krzysztof'
'Durka, Krzysztof'
'Luliński, Sergiusz'
_publ_section_title
;
 Highly electron-deficient 3,6-diaza-9-borafluorene scaffolds for the
 construction of luminescent chelate complexes.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              12133
_journal_page_last               12142
_journal_paper_doi               10.1039/d3sc03876a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C21 H12 B F2 N3 O'
_chemical_formula_sum            'C21 H12 B F2 N3 O'
_chemical_formula_weight         371.15
_chemical_melting_point          309
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-02-21 deposited with the CCDC.	2023-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.9080(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.0134(2)
_cell_length_b                   8.61830(10)
_cell_length_c                   11.09470(10)
_cell_measurement_reflns_used    6741
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.8230
_cell_measurement_theta_min      5.3620
_cell_volume                     1574.61(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.70a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_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  0.0295
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8250
_diffrn_reflns_point_group_measured_fraction_full 0.846
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.009
_diffrn_reflns_theta_min         5.372
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.566
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(9)
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2714
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0304
_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)+(0.0510P)²+0.9732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.691
_reflns_Friedel_fraction_max     0.634
_reflns_number_gt                2686
_reflns_number_total             2714
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc03876a3.cif
_cod_data_source_block           3f
_cod_depositor_comments
'Adding full bibliography for 1570062--1570068.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1570067
_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.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.695
_oxdiff_exptl_absorpt_empirical_full_max 1.340
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
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
F1 F 0.01759(9) 0.07377(19) 0.44638(15) 0.0246(4) Uani 1 1 d . . . . .
C15 C -0.00829(14) 0.2931(3) -0.1615(2) 0.0145(5) Uani 1 1 d . . . . .
F2 F -0.11948(9) 0.21266(18) 0.38169(15) 0.0232(4) Uani 1 1 d . . . . .
C14 C -0.03496(15) 0.2206(3) -0.2843(3) 0.0177(5) Uani 1 1 d . . . . .
H14 H -0.0035 0.2279 -0.3352 0.021 Uiso 1 1 calc R U . . .
C16 C 0.06664(14) 0.3850(3) -0.1049(2) 0.0148(5) Uani 1 1 d . . . . .
N3 N -0.05521(12) 0.2862(2) -0.0914(2) 0.0143(4) Uani 1 1 d . . . . .
O1 O 0.01724(10) 0.51326(19) 0.03927(17) 0.0154(4) Uani 1 1 d . . . . .
C6 C -0.07363(13) 0.2971(3) 0.2192(2) 0.0139(5) Uani 1 1 d . . . . .
C21 C 0.07423(14) 0.4990(3) -0.0103(2) 0.0141(5) Uani 1 1 d . . . . .
C10 C -0.09067(14) 0.3905(3) 0.1065(2) 0.0144(5) Uani 1 1 d . . . . .
C20 C 0.13981(15) 0.6015(3) 0.0303(2) 0.0166(5) Uani 1 1 d . . . . .
H20 H 0.1436 0.6823 0.0907 0.020 Uiso 1 1 calc R U . . .
C19 C 0.19950(14) 0.5849(3) -0.0180(2) 0.0185(5) Uani 1 1 d . . . . .
H19 H 0.2436 0.6558 0.0089 0.022 Uiso 1 1 calc R U . . .
C9 C -0.16046(14) 0.4813(3) 0.0615(2) 0.0167(5) Uani 1 1 d . . . . .
H9 H -0.1732 0.5464 -0.0133 0.020 Uiso 1 1 calc R U . . .
N1 N 0.11313(13) 0.0362(2) 0.3697(2) 0.0194(4) Uani 1 1 d . . . . .
C8 C -0.21140(14) 0.4750(3) 0.1279(3) 0.0179(5) Uani 1 1 d . . . . .
H8 H -0.2591 0.5369 0.0965 0.021 Uiso 1 1 calc R U . . .
C7 C -0.12972(15) 0.3017(3) 0.2754(2) 0.0168(5) Uani 1 1 d . . . . .
C1 C 0.00367(15) 0.2105(3) 0.2525(3) 0.0150(5) Uani 1 1 d . . . . .
N2 N -0.19624(12) 0.3855(3) 0.2344(2) 0.0184(4) Uani 1 1 d . . . . .
C17 C 0.12875(15) 0.3672(3) -0.1494(2) 0.0175(5) Uani 1 1 d . . . . .
H17 H 0.1251 0.2869 -0.2102 0.021 Uiso 1 1 calc R U . . .
C12 C -0.15399(15) 0.1322(3) -0.2590(3) 0.0191(5) Uani 1 1 d . . . . .
H12 H -0.2039 0.0770 -0.2906 0.023 Uiso 1 1 calc R U . . .
C2 C 0.03725(14) 0.2441(3) 0.1611(2) 0.0151(5) Uani 1 1 d . . . . .
C13 C -0.10664(15) 0.1384(3) -0.3320(3) 0.0191(5) Uani 1 1 d . . . . .
H13 H -0.1238 0.0861 -0.4142 0.023 Uiso 1 1 calc R U . . .
C4 C 0.14450(14) 0.0671(3) 0.2810(3) 0.0205(5) Uani 1 1 d . . . . .
H4 H 0.1934 0.0165 0.2905 0.025 Uiso 1 1 calc R U . . .
C11 C -0.12602(15) 0.2085(3) -0.1397(3) 0.0177(5) Uani 1 1 d . . . . .
H11 H -0.1580 0.2061 -0.0895 0.021 Uiso 1 1 calc R U . . .
B1 B -0.02087(16) 0.3672(3) 0.0520(3) 0.0151(5) Uani 1 1 d . . . . .
C5 C 0.04557(15) 0.1081(3) 0.3537(2) 0.0172(5) Uani 1 1 d . . . . .
C18 C 0.19550(15) 0.4656(3) -0.1054(3) 0.0185(5) Uani 1 1 d . . . . .
H18 H 0.2380 0.4518 -0.1344 0.022 Uiso 1 1 calc R U . . .
C3 C 0.10936(14) 0.1685(3) 0.1769(2) 0.0171(5) Uani 1 1 d . . . . .
H3 H 0.1338 0.1867 0.1167 0.021 Uiso 1 1 calc R U . . .
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'
O O 0.0492 0.0322 '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'
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
N3 C15 C14 119.3(2) . . ?
N3 C15 C16 117.1(2) . . ?
C14 C15 C16 123.5(2) . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C17 C16 C21 119.3(2) . . ?
C17 C16 C15 121.1(2) . . ?
C21 C16 C15 119.4(2) . . ?
C11 N3 C15 120.1(2) . . ?
C11 N3 B1 122.1(2) . . ?
C15 N3 B1 117.73(19) . . ?
C21 O1 B1 115.00(18) . . ?
C7 C6 C10 116.4(2) . . ?
C7 C6 C1 133.0(2) . . ?
C10 C6 C1 110.6(2) . . ?
O1 C21 C20 119.6(2) . . ?
O1 C21 C16 120.5(2) . . ?
C20 C21 C16 119.8(2) . . ?
C9 C10 C6 118.7(2) . . ?
C9 C10 B1 131.6(2) . . ?
C6 C10 B1 109.7(2) . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C5 N1 C4 116.7(2) . . ?
N2 C8 C9 123.1(2) . . ?
N2 C8 H8 118.5 . . ?
C9 C8 H8 118.5 . . ?
N2 C7 F2 113.3(2) . . ?
N2 C7 C6 126.1(2) . . ?
F2 C7 C6 120.6(2) . . ?
C5 C1 C2 117.6(2) . . ?
C5 C1 C6 131.9(2) . . ?
C2 C1 C6 110.5(2) . . ?
C7 N2 C8 116.9(2) . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C11 C12 C13 117.9(2) . . ?
C11 C12 H12 121.1 . . ?
C13 C12 H12 121.1 . . ?
C3 C2 C1 117.5(2) . . ?
C3 C2 B1 132.8(2) . . ?
C1 C2 B1 109.6(2) . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
N1 C4 C3 123.5(2) . . ?
N1 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
N3 C11 C12 122.6(2) . . ?
N3 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
O1 B1 N3 106.5(2) . . ?
O1 B1 C10 113.3(2) . . ?
N3 B1 C10 112.20(19) . . ?
O1 B1 C2 116.4(2) . . ?
N3 B1 C2 108.95(18) . . ?
C10 B1 C2 99.57(19) . . ?
N1 C5 F1 113.9(2) . . ?
N1 C5 C1 125.5(2) . . ?
F1 C5 C1 120.5(2) . . ?
C17 C18 C19 119.2(2) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C4 C3 C2 119.1(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
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
F1 C5 1.349(3) . ?
C15 N3 1.363(3) . ?
C15 C14 1.396(3) . ?
C15 C16 1.468(3) . ?
F2 C7 1.355(3) . ?
C14 C13 1.377(3) . ?
C14 H14 0.9500 . ?
C16 C17 1.402(3) . ?
C16 C21 1.404(3) . ?
N3 C11 1.345(3) . ?
N3 B1 1.613(3) . ?
O1 C21 1.352(3) . ?
O1 B1 1.468(3) . ?
C6 C7 1.386(3) . ?
C6 C10 1.412(3) . ?
C6 C1 1.489(3) . ?
C21 C20 1.395(3) . ?
C10 C9 1.390(3) . ?
C10 B1 1.614(3) . ?
C20 C19 1.389(4) . ?
C20 H20 0.9500 . ?
C19 C18 1.395(4) . ?
C19 H19 0.9500 . ?
C9 C8 1.392(4) . ?
C9 H9 0.9500 . ?
N1 C5 1.312(3) . ?
N1 C4 1.345(4) . ?
C8 N2 1.343(4) . ?
C8 H8 0.9500 . ?
C7 N2 1.313(3) . ?
C1 C5 1.386(3) . ?
C1 C2 1.406(4) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C12 C11 1.378(4) . ?
C12 C13 1.395(4) . ?
C12 H12 0.9500 . ?
C2 C3 1.399(3) . ?
C2 B1 1.630(4) . ?
C13 H13 0.9500 . ?
C4 C3 1.381(4) . ?
C4 H4 0.9500 . ?
C11 H11 0.9500 . ?
C18 H18 0.9500 . ?
C3 H3 0.9500 . ?
