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#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/38/7233874.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_7233874
loop_
_publ_author_name
'Alexander N. Chernyshev'
'Dmitry Morozov'
'Jarkko Mutanen'
'Vadim Yu Kukushkin'
'Gerrit Groenhof'
'Matti Haukka'
_publ_section_title
;
 Weak intermolecular interactions promote blue luminescence of protonated
 2,2'-dipyridylamine salts
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              8285
_journal_page_last               8294
_journal_paper_doi               10.1039/C4TC01165A
_journal_volume                  2
_journal_year                    2014
_chemical_formula_moiety         'C10 H10 N3, B F4'
_chemical_formula_sum            'C10 H10 B F4 N3'
_chemical_formula_weight         259.02
_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   mixed
_cell_angle_alpha                90
_cell_angle_beta                 103.447(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2733(5)
_cell_length_b                   15.9517(10)
_cell_length_c                   8.6360(5)
_cell_measurement_reflns_used    3952
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.84
_cell_measurement_theta_min      2.53
_cell_volume                     1108.48(12)
_computing_cell_refinement       'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2008)'
_computing_data_reduction        'Denzo/Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
'CrystaMaker (CrystalMaker Software ltd., 2011)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2013)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II CCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10637
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.531
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7537
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1456 before and 0.0635 after correction.
The Ratio of minimum to maximum transmission is 0.7537.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.371
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0469
_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)+(0.0600P)²+0.3871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1331
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1870
_reflns_number_total             2542
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000010.cif
_cod_data_source_block           PCOD1000010
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7233874
_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_min   0.944
_shelx_estimated_absorpt_t_max   0.949
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
N3 N -0.15613(17) 0.32520(9) 0.45652(17) 0.0267(3) Uani 1 1 d . . . . .
N1 N 0.06457(18) 0.26279(9) 0.37674(18) 0.0300(4) Uani 1 1 d . . . . .
H1N H 0.1161 0.2155 0.3675 0.036 Uiso 1 1 calc R U . . .
N2 N 0.06351(17) 0.40733(9) 0.34006(16) 0.0247(3) Uani 1 1 d . . . . .
C6 C -0.0762(2) 0.25475(10) 0.43748(19) 0.0231(4) Uani 1 1 d . . . . .
C7 C -0.1275(2) 0.17562(10) 0.47457(19) 0.0248(4) Uani 1 1 d . . . . .
H7 H -0.0667 0.1268 0.4605 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1290(2) 0.47914(11) 0.2970(2) 0.0274(4) Uani 1 1 d . . . . .
H5 H 0.0765 0.5312 0.3065 0.033 Uiso 1 1 calc R U . . .
C10 C -0.2938(2) 0.31834(11) 0.5127(2) 0.0275(4) Uani 1 1 d . . . . .
H10 H -0.3524 0.3680 0.5263 0.033 Uiso 1 1 calc R U . . .
C1 C 0.1348(2) 0.33202(10) 0.32959(19) 0.0236(4) Uani 1 1 d . . . . .
C8 C -0.2687(2) 0.17029(11) 0.5321(2) 0.0289(4) Uani 1 1 d . . . . .
H8 H -0.3076 0.1173 0.5582 0.035 Uiso 1 1 calc R U . . .
C2 C 0.2778(2) 0.32798(11) 0.2696(2) 0.0275(4) Uani 1 1 d . . . . .
H2 H 0.3285 0.2755 0.2593 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2689(2) 0.47738(11) 0.2402(2) 0.0285(4) Uani 1 1 d . . . . .
H4 H 0.3151 0.5278 0.2106 0.034 Uiso 1 1 calc R U . . .
B1 B -0.3008(2) 0.57581(14) 0.2531(2) 0.0281(4) Uani 1 1 d . . . . .
C9 C -0.3538(2) 0.24293(11) 0.5516(2) 0.0293(4) Uani 1 1 d . . . . .
H9 H -0.4517 0.2406 0.5911 0.035 Uiso 1 1 calc R U . . .
C3 C 0.3438(2) 0.40003(11) 0.2262(2) 0.0298(4) Uani 1 1 d . . . . .
H3A H 0.4414 0.3977 0.1862 0.036 Uiso 1 1 calc R U . . .
F2A F -0.3701(10) 0.6248(4) 0.3434(8) 0.0594(17) Uani 0.638(9) 1 d . . P A 1
F1A F -0.2329(6) 0.5039(3) 0.3431(4) 0.0395(9) Uani 0.638(9) 1 d . . P A 1
F4A F -0.4152(3) 0.5438(2) 0.1211(3) 0.0483(9) Uani 0.638(9) 1 d . . P A 1
F3A F -0.1741(3) 0.61016(18) 0.1926(7) 0.0493(11) Uani 0.638(9) 1 d . . P A 1
F4B F -0.1508(5) 0.6247(3) 0.3013(13) 0.052(2) Uani 0.362(9) 1 d . . P A 2
F3B F -0.3566(17) 0.5953(10) 0.1031(7) 0.157(7) Uani 0.362(9) 1 d . . P A 2
F1B F -0.2738(14) 0.5026(6) 0.2994(16) 0.080(3) Uani 0.362(9) 1 d . . P A 2
F2B F -0.4074(17) 0.6267(7) 0.3156(16) 0.062(3) Uani 0.362(9) 1 d . . P A 2
H2N H -0.0540(18) 0.3919(10) 0.3849(17) 0.008(4) Uiso 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 0.0033 0.0016 '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 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C6 N3 C10 117.58(14) . .
C1 N1 C6 130.13(15) . .
C1 N1 H1N 114.9 . .
C6 N1 H1N 114.9 . .
C1 N2 C5 121.64(14) . .
C1 N2 H2N 104.3(8) . .
C5 N2 H2N 134.0(8) . .
N3 C6 N1 116.87(14) . .
N3 C6 C7 123.28(15) . .
N1 C6 C7 119.84(15) . .
C8 C7 C6 118.01(16) . .
C8 C7 H7 121.0 . .
C6 C7 H7 121.0 . .
N2 C5 C4 120.68(16) . .
N2 C5 H5 119.7 . .
C4 C5 H5 119.7 . .
N3 C10 C9 123.06(16) . .
N3 C10 H10 118.5 . .
C9 C10 H10 118.5 . .
N2 C1 N1 118.76(15) . .
N2 C1 C2 119.05(14) . .
N1 C1 C2 122.19(15) . .
C7 C8 C9 119.39(16) . .
C7 C8 H8 120.3 . .
C9 C8 H8 120.3 . .
C3 C2 C1 119.39(16) . .
C3 C2 H2 120.3 . .
C1 C2 H2 120.3 . .
C5 C4 C3 118.77(16) . .
C5 C4 H4 120.6 . .
C3 C4 H4 120.6 . .
F1B B1 F3B 122.7(7) . .
F2A B1 F3A 117.2(4) . .
F1B B1 F2B 120.4(7) . .
F3B B1 F2B 97.8(7) . .
F2A B1 F4A 113.0(4) . .
F3A B1 F4A 105.3(3) . .
F2A B1 F1A 108.9(4) . .
F3A B1 F1A 106.7(2) . .
F4A B1 F1A 104.9(3) . .
F1B B1 F4B 109.8(5) . .
F3B B1 F4B 103.9(7) . .
F2B B1 F4B 98.8(5) . .
C10 C9 C8 118.67(16) . .
C10 C9 H9 120.7 . .
C8 C9 H9 120.7 . .
C2 C3 C4 120.44(16) . .
C2 C3 H3A 119.8 . .
C4 C3 H3A 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N3 C6 1.334(2) .
N3 C10 1.342(2) .
N1 C1 1.354(2) .
N1 C6 1.390(2) .
N1 H1N 0.8800 .
N2 C1 1.350(2) .
N2 C5 1.356(2) .
N2 H2N 1.154(14) .
C6 C7 1.393(2) .
C7 C8 1.374(2) .
C7 H7 0.9500 .
C5 C4 1.358(2) .
C5 H5 0.9500 .
C10 C9 1.373(2) .
C10 H10 0.9500 .
C1 C2 1.400(2) .
C8 C9 1.386(3) .
C8 H8 0.9500 .
C2 C3 1.362(2) .
C2 H2 0.9500 .
C4 C3 1.399(3) .
C4 H4 0.9500 .
B1 F1B 1.238(10) .
B1 F3B 1.308(7) .
B1 F2A 1.326(6) .
B1 F3A 1.388(3) .
B1 F2B 1.397(13) .
B1 F4A 1.398(3) .
B1 F1A 1.426(5) .
B1 F4B 1.442(5) .
C9 H9 0.9500 .
C3 H3A 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1N F3A 0.88 1.85 2.713(3) 164.9 2_545 yes
N1 H1N F4B 0.88 2.12 2.870(6) 142.6 2_545 yes
N2 H2N N3 1.154(14) 1.572(15) 2.6230(19) 148.0(12) . yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168338814
