#------------------------------------------------------------------------------
#$Date: 2019-09-16 12:14:22 +0300 (Mon, 16 Sep 2019) $
#$Revision: 218318 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/38/7233872.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_7233872
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                117.066(2)
_cell_angle_beta                 100.294(3)
_cell_angle_gamma                98.373(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1604(10)
_cell_length_b                   9.0853(5)
_cell_length_c                   9.8694(6)
_cell_measurement_reflns_used    3284
_cell_measurement_temperature    290(2)
_cell_volume                     543.33(9)
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_molecular_graphics
'CrystaMaker (CrystalMaker Software ltd., 2011)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0370
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9282
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.413
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9064
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.597
_exptl_crystal_description       block
_exptl_crystal_F_000             270
_exptl_crystal_size_max          0.667
_exptl_crystal_size_mid          0.556
_exptl_crystal_size_min          0.229
_exptl_transmission_factor_max   0.98003
_exptl_transmission_factor_min   0.94928
_refine_diff_density_max         1.586
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0712
_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)+(0.1248P)²+0.4974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2060
_refine_ls_wR_factor_ref         0.2268
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1696
_reflns_number_total             2478
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000008.cif
_cod_data_source_block           PCOD1000008
_cod_original_formula_sum        'C10 H12 F3 N3 O Si0.50'
_cod_database_code               7233872
_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   0.882
_shelx_estimated_absorpt_t_max   0.957
_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
F3 F 0.5107(4) 0.4217(3) 0.8119(3) 0.0620(7) Uani 1 1 d . . . . .
O1S O 0.9156(4) 0.3454(4) 0.7936(4) 0.0668(9) Uani 1 1 d . . . . .
H1O H 1.0231 0.4126 0.8500 0.100 Uiso 1 1 d R U . . .
H2O H 0.8419 0.3708 0.8508 0.100 Uiso 1 1 d R U . . .
F1 F 0.6705(4) 0.4012(3) 1.0310(3) 0.0633(7) Uani 1 1 d . . . . .
F2 F 0.6764(4) 0.6719(3) 1.0541(3) 0.0697(8) Uani 1 1 d . . . . .
N3 N 0.8678(4) 0.6139(4) 0.6454(4) 0.0428(7) Uani 1 1 d . . . . .
Si1 Si 0.5000 0.5000 1.0000 0.0349(4) Uani 1 2 d S . P . .
C9 C 1.0346(5) 0.9089(5) 0.7979(5) 0.0453(9) Uani 1 1 d . . . . .
H9 H 1.1161 1.0009 0.8926 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5305(5) 0.0000(5) 0.3038(4) 0.0401(8) Uani 1 1 d . . . . .
H4 H 0.5033 -0.1116 0.2859 0.048 Uiso 1 1 calc R U . . .
C5 C 0.6460(5) 0.1295(5) 0.4447(4) 0.0396(8) Uani 1 1 d . . . . .
H5 H 0.6963 0.1071 0.5250 0.048 Uiso 1 1 calc R U . . .
C6 C 0.7962(5) 0.6381(4) 0.5246(4) 0.0353(7) Uani 1 1 d . . . . .
C7 C 0.8380(5) 0.7948(5) 0.5344(4) 0.0415(8) Uani 1 1 d . . . . .
H7 H 0.7856 0.8080 0.4486 0.050 Uiso 1 1 calc R U . . .
N1 N 0.6724(5) 0.4922(5) 0.3935(4) 0.0550(9) Uani 1 1 d . . . . .
H1N H 0.6192 0.5109 0.3196 0.066 Uiso 1 1 calc R U . . .
C10 C 0.9897(6) 0.7513(5) 0.7817(4) 0.0448(9) Uani 1 1 d . . . . .
H10 H 1.0432 0.7357 0.8658 0.054 Uiso 1 1 calc R U . . .
C8 C 0.9585(6) 0.9325(5) 0.6729(5) 0.0461(9) Uani 1 1 d . . . . .
H8 H 0.9884 1.0403 0.6822 0.055 Uiso 1 1 calc R U . . .
C1 C 0.6168(5) 0.3289(4) 0.3561(4) 0.0337(7) Uani 1 1 d . . . . .
C2 C 0.4943(5) 0.1980(5) 0.2106(4) 0.0378(8) Uani 1 1 d . . . . .
H2 H 0.4418 0.2218 0.1318 0.045 Uiso 1 1 calc R U . . .
C3 C 0.4523(5) 0.0352(5) 0.1851(4) 0.0392(8) Uani 1 1 d . . . . .
H3 H 0.3710 -0.0531 0.0882 0.047 Uiso 1 1 calc R U . . .
N2 N 0.6894(4) 0.2915(4) 0.4704(3) 0.0386(7) Uani 1 1 d . . . . .
H2N H 0.7988 0.4436 0.5935 0.058 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
_geom_angle_publ_flag
H1O O1S H2O 104.6 . . ?
C6 N3 C10 118.1(3) . . ?
C6 N3 H2N 106.4 . . ?
C10 N3 H2N 135.4 . . ?
F2 Si1 F2 180.0 . 2_667 ?
F2 Si1 F3 89.73(14) . . ?
F2 Si1 F3 90.27(14) 2_667 . ?
F2 Si1 F3 90.27(14) . 2_667 ?
F2 Si1 F3 89.73(14) 2_667 2_667 ?
F3 Si1 F3 180.0(2) . 2_667 ?
F2 Si1 F1 90.14(14) . 2_667 ?
F2 Si1 F1 89.86(14) 2_667 2_667 ?
F3 Si1 F1 90.86(13) . 2_667 ?
F3 Si1 F1 89.14(13) 2_667 2_667 ?
F2 Si1 F1 89.86(14) . . ?
F2 Si1 F1 90.14(14) 2_667 . ?
F3 Si1 F1 89.14(13) . . ?
F3 Si1 F1 90.86(13) 2_667 . ?
F1 Si1 F1 180.0 2_667 . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 N2 120.7(3) . . ?
C4 C5 H5 119.7 . . ?
N2 C5 H5 119.7 . . ?
N3 C6 C7 122.3(3) . . ?
N3 C6 N1 113.6(3) . . ?
C7 C6 N1 124.0(3) . . ?
C6 C7 C8 119.0(4) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C1 N1 C6 134.2(3) . . yes
C1 N1 H1N 112.9 . . ?
C6 N1 H1N 112.9 . . ?
C9 C10 N3 121.9(4) . . ?
C9 C10 H10 119.1 . . ?
N3 C10 H10 119.1 . . ?
C7 C8 C9 119.2(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
N1 C1 N2 116.0(3) . . ?
N1 C1 C2 124.7(3) . . ?
N2 C1 C2 119.4(3) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 N2 C1 121.2(3) . . ?
C5 N2 H2N 134.7 . . ?
C1 N2 H2N 104.2 . . ?
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
F3 Si1 1.680(2) . ?
O1S H1O 0.8222 . ?
O1S H2O 0.8214 . ?
F1 Si1 1.681(2) . ?
F2 Si1 1.657(2) . ?
N3 C6 1.336(5) . ?
N3 C10 1.365(5) . ?
N3 H2N 1.3661 . ?
Si1 F2 1.657(2) 2_667 ?
Si1 F3 1.680(2) 2_667 ?
Si1 F1 1.681(2) 2_667 ?
C9 C10 1.348(6) . ?
C9 C8 1.378(6) . ?
C9 H9 0.9300 . ?
C4 C5 1.349(5) . ?
C4 C3 1.395(5) . ?
C4 H4 0.9300 . ?
C5 N2 1.351(5) . yes
C5 H5 0.9300 . ?
C6 C7 1.366(5) . ?
C6 N1 1.380(5) . ?
C7 C8 1.373(5) . ?
C7 H7 0.9300 . ?
N1 C1 1.332(5) . yes
N1 H1N 0.8600 . ?
C10 H10 0.9300 . ?
C8 H8 0.9300 . ?
C1 N2 1.360(5) . ?
C1 C2 1.392(5) . ?
C2 C3 1.359(5) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
N2 H2N 1.3475 . yes
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 F3 0.86 1.84 2.689(4) 169.9 2_666 yes
N2 H2N N3 1.35 1.37 2.591(4) 145.5 . yes
