#------------------------------------------------------------------------------
#$Date: 2024-01-06 09:19:12 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/00/1570065.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_1570065
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         'C23 H14 B F2 N3 O'
_chemical_formula_sum            'C23 H14 B F2 N3 O'
_chemical_formula_weight         397.18
_chemical_melting_point          250
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/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                 97.4790(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6135(2)
_cell_length_b                   6.83220(10)
_cell_length_c                   20.0023(3)
_cell_measurement_reflns_used    9106
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.3070
_cell_measurement_theta_min      4.4490
_cell_volume                     1844.59(5)
_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 0.998
_diffrn_measured_fraction_theta_max 0.987
_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  0.0257
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15449
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.614
_diffrn_reflns_theta_min         4.459
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.690
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.70a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0384
_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)+(0.0672P)²+0.5365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3431
_reflns_number_total             3888
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc03876a3.cif
_cod_data_source_block           3b
_cod_depositor_comments
'Adding full bibliography for 1570062--1570068.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1570065
_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 0.800
_oxdiff_exptl_absorpt_empirical_full_max 1.530
_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.21686(6) 0.91901(13) 0.13370(4) 0.0322(2) Uani 1 1 d . . . . .
F2 F 0.11030(7) 0.60222(14) 0.11723(4) 0.0367(2) Uani 1 1 d . . . . .
O1 O 0.38838(6) 0.54710(13) -0.07853(4) 0.0225(2) Uani 1 1 d . . . . .
N3 N 0.24284(7) 0.68229(15) -0.15258(5) 0.0197(2) Uani 1 1 d . . . . .
N2 N 0.31782(8) 1.09606(17) 0.07783(6) 0.0276(2) Uani 1 1 d . . . . .
N1 N 0.08639(8) 0.34808(18) 0.04672(6) 0.0285(3) Uani 1 1 d . . . . .
C4 C 0.10356(9) 0.2571(2) -0.00991(7) 0.0271(3) Uani 1 1 d . . . . .
H4 H 0.0715 0.1356 -0.0207 0.033 Uiso 1 1 calc R U . . .
C7 C 0.30243(9) 0.82547(19) -0.02770(6) 0.0211(3) Uani 1 1 d . . . . .
C18 C 0.34642(9) 0.43614(18) -0.19207(6) 0.0209(2) Uani 1 1 d . . . . .
C1 C 0.19524(9) 0.60674(19) 0.02091(6) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.21320(9) 0.50817(19) -0.03821(6) 0.0212(3) Uani 1 1 d . . . . .
C6 C 0.24999(9) 0.79552(19) 0.02781(6) 0.0220(3) Uani 1 1 d . . . . .
C23 C 0.40757(9) 0.43295(18) -0.12926(6) 0.0208(2) Uani 1 1 d . . . . .
C16 C 0.18558(9) 0.97048(19) -0.21848(6) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.2439 0.9649 -0.2399 0.028 Uiso 1 1 calc R U . . .
C11 C 0.17075(8) 0.83523(18) -0.16890(6) 0.0205(2) Uani 1 1 d . . . . .
C9 C 0.36694(10) 1.1223(2) 0.02451(7) 0.0272(3) Uani 1 1 d . . . . .
H9 H 0.4071 1.2356 0.0232 0.033 Uiso 1 1 calc R U . . .
C3 C 0.16569(9) 0.33066(19) -0.05375(7) 0.0243(3) Uani 1 1 d . . . . .
H3 H 0.1755 0.2612 -0.0935 0.029 Uiso 1 1 calc R U . . .
C19 C 0.36809(9) 0.31651(19) -0.24547(6) 0.0228(3) Uani 1 1 d . . . . .
H19 H 0.3265 0.3193 -0.2875 0.027 Uiso 1 1 calc R U . . .
C17 C 0.26852(9) 0.57805(18) -0.20175(6) 0.0205(2) Uani 1 1 d . . . . .
H17 H 0.2343 0.5967 -0.2458 0.025 Uiso 1 1 calc R U . . .
C10 C 0.26243(9) 0.9381(2) 0.07746(6) 0.0245(3) Uani 1 1 d . . . . .
C5 C 0.13147(9) 0.5162(2) 0.06020(6) 0.0256(3) Uani 1 1 d . . . . .
C22 C 0.49230(9) 0.3147(2) -0.12198(6) 0.0250(3) Uani 1 1 d . . . . .
H22 H 0.5362 0.3153 -0.0810 0.030 Uiso 1 1 calc R U . . .
C20 C 0.44960(10) 0.1953(2) -0.23688(7) 0.0262(3) Uani 1 1 d . . . . .
H20 H 0.4637 0.1116 -0.2723 0.031 Uiso 1 1 calc R U . . .
C15 C 0.11477(10) 1.11383(19) -0.23659(7) 0.0261(3) Uani 1 1 d . . . . .
H15 H 0.1241 1.2057 -0.2708 0.031 Uiso 1 1 calc R U . . .
C12 C 0.08606(9) 0.84162(19) -0.13671(6) 0.0223(3) Uani 1 1 d . . . . .
H12 H 0.0763 0.7487 -0.1029 0.027 Uiso 1 1 calc R U . . .
C13 C 0.01609(9) 0.9867(2) -0.15511(6) 0.0247(3) Uani 1 1 d . . . . .
H13 H -0.0421 0.9928 -0.1336 0.030 Uiso 1 1 calc R U . . .
C14 C 0.03015(9) 1.1227(2) -0.20451(7) 0.0258(3) Uani 1 1 d . . . . .
H14 H -0.0180 1.2217 -0.2164 0.031 Uiso 1 1 calc R U . . .
C21 C 0.51156(10) 0.1971(2) -0.17505(7) 0.0276(3) Uani 1 1 d . . . . .
H21 H 0.5684 0.1152 -0.1695 0.033 Uiso 1 1 calc R U . . .
C8 C 0.36145(9) 0.9907(2) -0.02871(7) 0.0250(3) Uani 1 1 d . . . . .
H8 H 0.3977 1.0136 -0.0654 0.030 Uiso 1 1 calc R U . . .
B1 B 0.28932(10) 0.6367(2) -0.07662(7) 0.0205(3) 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'
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'
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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 3 0.0639
5 0 -3 0.0676
2 -2 -1 0.1610
-2 4 1 0.1372
0 0 -1 0.0231
0 0 1 0.0456
0 -1 5 0.1139
3 0 5 0.0694
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
C23 O1 B1 121.95(10) . . ?
C17 N3 C11 117.94(10) . . ?
C17 N3 B1 120.05(10) . . ?
C11 N3 B1 122.00(10) . . ?
C10 N2 C9 116.71(12) . . ?
C5 N1 C4 116.81(11) . . ?
N1 C4 C3 123.62(13) . . ?
N1 C4 H4 118.2 . . ?
C3 C4 H4 118.2 . . ?
C8 C7 C6 118.86(12) . . ?
C8 C7 B1 131.28(11) . . ?
C6 C7 B1 109.50(11) . . ?
C19 C18 C23 120.56(11) . . ?
C19 C18 C17 121.05(11) . . ?
C23 C18 C17 118.09(11) . . ?
C5 C1 C2 116.81(12) . . ?
C5 C1 C6 132.53(12) . . ?
C2 C1 C6 110.65(11) . . ?
C3 C2 C1 118.55(11) . . ?
C3 C2 B1 132.23(11) . . ?
C1 C2 B1 109.22(11) . . ?
C10 C6 C7 115.78(12) . . ?
C10 C6 C1 133.58(12) . . ?
C7 C6 C1 110.58(11) . . ?
O1 C23 C22 119.93(11) . . ?
O1 C23 C18 121.10(11) . . ?
C22 C23 C18 118.88(11) . . ?
C11 C16 C15 119.65(11) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C11 C12 121.01(11) . . ?
C16 C11 N3 119.06(11) . . ?
C12 C11 N3 119.89(11) . . ?
N2 C9 C8 122.68(12) . . ?
N2 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
C4 C3 C2 118.56(12) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C20 C19 C18 119.99(12) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
N3 C17 C18 122.46(11) . . ?
N3 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
N2 C10 F1 113.38(11) . . ?
N2 C10 C6 126.66(12) . . ?
F1 C10 C6 119.94(12) . . ?
N1 C5 F2 114.16(11) . . ?
N1 C5 C1 125.64(12) . . ?
F2 C5 C1 120.19(12) . . ?
C21 C22 C23 119.42(12) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C19 C20 C21 119.12(12) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C16 C15 C14 119.92(12) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C13 C12 C11 118.67(12) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C14 C13 C12 120.83(12) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.92(12) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C22 C21 C20 121.95(12) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C7 C8 C9 119.31(12) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
O1 B1 N3 107.70(9) . . ?
O1 B1 C7 108.40(10) . . ?
N3 B1 C7 114.79(10) . . ?
O1 B1 C2 115.21(10) . . ?
N3 B1 C2 110.89(9) . . ?
C7 B1 C2 99.90(10) . . ?
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 C10 1.3599(14) . ?
F2 C5 1.3474(15) . ?
O1 C23 1.3324(15) . ?
O1 B1 1.4861(15) . ?
N3 C17 1.2986(16) . ?
N3 C11 1.4416(15) . ?
N3 B1 1.5986(16) . ?
N2 C10 1.3160(18) . ?
N2 C9 1.3425(18) . ?
N1 C5 1.3137(18) . ?
N1 C4 1.3392(18) . ?
C4 C3 1.3892(18) . ?
C4 H4 0.9500 . ?
C7 C8 1.3876(18) . ?
C7 C6 1.4110(16) . ?
C7 B1 1.6145(18) . ?
C18 C19 1.4065(17) . ?
C18 C23 1.4139(17) . ?
C18 C17 1.4313(16) . ?
C1 C5 1.3897(18) . ?
C1 C2 1.4096(17) . ?
C1 C6 1.4871(17) . ?
C2 C3 1.3905(18) . ?
C2 B1 1.6257(18) . ?
C6 C10 1.3856(18) . ?
C23 C22 1.4002(17) . ?
C16 C11 1.3894(18) . ?
C16 C15 1.3888(18) . ?
C16 H16 0.9500 . ?
C11 C12 1.3924(17) . ?
C9 C8 1.3879(19) . ?
C9 H9 0.9500 . ?
C3 H3 0.9500 . ?
C19 C20 1.3774(18) . ?
C19 H19 0.9500 . ?
C17 H17 0.9500 . ?
C22 C21 1.3832(19) . ?
C22 H22 0.9500 . ?
C20 C21 1.4035(19) . ?
C20 H20 0.9500 . ?
C15 C14 1.3909(19) . ?
C15 H15 0.9500 . ?
C12 C13 1.3906(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3875(19) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C21 H21 0.9500 . ?
C8 H8 0.9500 . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.9970 0.0045 2.9858 -0.1062 -0.5728 -0.0749
4.9970 -0.0045 -2.9858 0.1062 0.5728 0.0749
1.9972 -2.0027 -0.9464 0.0256 0.1689 0.4771
-1.9958 4.0042 0.8985 -0.0242 -0.1101 -0.9244
0.0010 -0.0027 -1.0003 0.0774 0.0070 0.0011
-0.0010 0.0027 1.0003 -0.0774 -0.0070 -0.0011
-0.0055 -0.9870 5.0256 -0.3875 -0.0645 0.2180
2.9917 0.0160 5.0107 -0.4623 0.2960 0.0372
