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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/7/23/38/7233871.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_7233871
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, F3 Si0.5, H2 O'
_chemical_formula_sum            'C10 H12 F3 N3 O Si0.5'
_chemical_formula_weight         261.27
_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
_cell_angle_alpha                117.118(8)
_cell_angle_beta                 99.869(6)
_cell_angle_gamma                98.207(6)
_cell_formula_units_Z            2
_cell_length_a                   7.1165(5)
_cell_length_b                   9.0759(7)
_cell_length_c                   9.8120(8)
_cell_measurement_reflns_used    2652
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      30.5330
_cell_measurement_theta_min      2.4140
_cell_volume                     537.81(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
'CrystaMaker (CrystalMaker Software ltd., 2012)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0089
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4321
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.492
_diffrn_reflns_theta_min         2.421
_diffrn_source                   micro-source
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_description       block
_exptl_crystal_F_000             270
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.101
_refine_diff_density_max         2.163
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0666
_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)+(0.1078P)²+0.9532P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1911
_refine_ls_wR_factor_ref         0.1940
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2080
_reflns_number_total             2227
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000007.cif
_cod_data_source_block           PCOD1000007
_cod_original_cell_volume        537.80(8)
_cod_original_formula_sum        'C10 H12 F3 N3 O Si0.50'
_cod_database_code               7233871
_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   0.958
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2013-4
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 0.3281(4) 0.0083(4) 0.1069(3) 0.0378(7) Uani 1 1 d . . . . .
H1 H 0.3816 -0.0109 0.1831 0.045 Uiso 1 1 calc R U . . .
N3 N 0.1300(4) -0.1134(3) -0.1473(3) 0.0281(5) Uani 1 1 d . . . . .
C1 C 0.3832(4) 0.1713(3) 0.1437(3) 0.0236(6) Uani 1 1 d . . . . .
C2 C 0.5071(4) 0.3019(4) 0.2902(3) 0.0237(6) Uani 1 1 d . . . . .
H2 H 0.5610 0.2771 0.3705 0.028 Uiso 1 1 calc R U . . .
C3 C 0.5495(4) 0.4665(3) 0.3158(3) 0.0236(6) Uani 1 1 d . . . . .
H3 H 0.6336 0.5561 0.4145 0.028 Uiso 1 1 calc R U . . .
C4 C 0.4694(4) 0.5031(4) 0.1971(3) 0.0245(6) Uani 1 1 d . . . . .
H4 H 0.4968 0.6173 0.2158 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3522(4) 0.3733(4) 0.0552(3) 0.0253(6) Uani 1 1 d . . . . .
H5 H 0.2995 0.3969 -0.0263 0.030 Uiso 1 1 calc R U . . .
C6 C 0.2043(4) -0.1384(3) -0.0260(3) 0.0242(6) Uani 1 1 d . . . . .
C7 C 0.1623(4) -0.2961(4) -0.0348(3) 0.0254(6) Uani 1 1 d . . . . .
H7 H 0.2156 -0.3094 0.0534 0.030 Uiso 1 1 calc R U . . .
C8 C 0.0413(4) -0.4347(4) -0.1741(4) 0.0281(6) Uani 1 1 d . . . . .
H8 H 0.0115 -0.5449 -0.1835 0.034 Uiso 1 1 calc R U . . .
C9 C -0.0362(4) -0.4104(4) -0.3004(3) 0.0268(6) Uani 1 1 d . . . . .
H9 H -0.1196 -0.5039 -0.3972 0.032 Uiso 1 1 calc R U . . .
C10 C 0.0093(4) -0.2497(4) -0.2837(3) 0.0271(6) Uani 1 1 d . . . . .
H10 H -0.0450 -0.2332 -0.3696 0.033 Uiso 1 1 calc R U . . .
Si1 Si 0.5000 0.0000 0.5000 0.0220(3) Uani 1 2 d S . P . .
F1 F 0.5108(3) -0.0791(3) 0.3095(2) 0.0378(5) Uani 1 1 d . . . . .
F2 F 0.3268(3) 0.0990(3) 0.4694(2) 0.0423(5) Uani 1 1 d . . . . .
F3 F 0.3223(3) -0.1734(2) 0.4459(3) 0.0438(5) Uani 1 1 d . . . . .
O1 O 0.0836(3) 0.1564(3) -0.2927(3) 0.0407(6) Uani 1 1 d . . . . .
H1S H -0.0300 0.1013 -0.3478 0.061 Uiso 1 1 d R U . . .
H2S H 0.1561 0.1210 -0.3566 0.061 Uiso 1 1 d R U . . .
N2 N 0.3094(3) 0.2097(3) 0.0287(3) 0.0269(5) Uani 1 1 d . . . . .
H2N H 0.1997 0.0562 -0.0952 0.040 Uiso 1 1 d 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 0.0033 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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
C1 N1 C6 133.9(3) . .
C1 N1 H1 113.0 . .
C6 N1 H1 113.0 . .
C6 N3 C10 118.4(3) . .
C6 N3 H2N 106.1 . .
C10 N3 H2N 135.5 . .
N1 C1 N2 116.2(3) . .
N1 C1 C2 124.3(3) . .
N2 C1 C2 119.5(2) . .
C3 C2 C1 119.0(3) . .
C3 C2 H2 120.5 . .
C1 C2 H2 120.5 . .
C2 C3 C4 120.5(2) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C5 C4 C3 119.2(3) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
C4 C5 N2 120.7(3) . .
C4 C5 H5 119.6 . .
N2 C5 H5 119.6 . .
N3 C6 C7 122.5(3) . .
N3 C6 N1 113.9(3) . .
C7 C6 N1 123.6(3) . .
C6 C7 C8 118.9(3) . .
C6 C7 H7 120.5 . .
C8 C7 H7 120.5 . .
C7 C8 C9 119.1(3) . .
C7 C8 H8 120.5 . .
C9 C8 H8 120.5 . .
C10 C9 C8 119.3(3) . .
C10 C9 H9 120.4 . .
C8 C9 H9 120.4 . .
N3 C10 C9 121.8(3) . .
N3 C10 H10 119.1 . .
C9 C10 H10 119.1 . .
F3 Si1 F3 180.0 . 2_656
F3 Si1 F2 89.72(11) . .
F3 Si1 F2 90.28(11) 2_656 .
F3 Si1 F2 90.28(11) . 2_656
F3 Si1 F2 89.72(11) 2_656 2_656
F2 Si1 F2 180.0 . 2_656
F3 Si1 F1 90.00(10) . .
F3 Si1 F1 90.00(10) 2_656 .
F2 Si1 F1 90.77(10) . .
F2 Si1 F1 89.23(10) 2_656 .
F3 Si1 F1 90.00(10) . 2_656
F3 Si1 F1 90.00(10) 2_656 2_656
F2 Si1 F1 89.23(10) . 2_656
F2 Si1 F1 90.77(10) 2_656 2_656
F1 Si1 F1 180.00(14) . 2_656
H1S O1 H2S 104.6 . .
C5 N2 C1 121.1(2) . .
C5 N2 H2N 135.0 . .
C1 N2 H2N 103.9 . .
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 C1 1.331(4) . yes
N1 C6 1.392(4) . yes
N1 H1 0.8800 . ?
N3 C6 1.346(4) . ?
N3 C10 1.361(4) . ?
N3 H2N 1.3623 . ?
C1 N2 1.370(4) . ?
C1 C2 1.401(4) . ?
C2 C3 1.374(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.360(4) . ?
C4 H4 0.9500 . ?
C5 N2 1.363(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.379(4) . ?
C7 C8 1.382(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
Si1 F3 1.6723(18) . ?
Si1 F3 1.6723(18) 2_656 ?
Si1 F2 1.6891(18) . ?
Si1 F2 1.6891(18) 2_656 ?
Si1 F1 1.6904(18) . ?
Si1 F1 1.6904(18) 2_656 ?
O1 H1S 0.8274 . ?
O1 H2S 0.8586 . ?
N2 H2N 1.3593 . ?
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 H1 F1 0.88 1.80 2.668(3) 168.6 . yes
N2 H2N N3 1.36 1.36 2.602(3) 145.9 . yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168338812
