#------------------------------------------------------------------------------
#$Date: 2024-11-09 14:07:10 +0200 (Sat, 09 Nov 2024) $
#$Revision: 295862 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/38/7233865.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_7233865
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, F2 H, 0.5(H2 O)'
_chemical_formula_sum            'C10 H12 F2 N3 O0.5'
_chemical_formula_weight         220.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2b'
_space_group_name_H-M_alt        'P b c 21'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9450(2)
_cell_length_b                   7.63438(9)
_cell_length_c                   19.5974(3)
_cell_measurement_reflns_used    5611
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3160
_cell_measurement_theta_min      3.1560
_cell_volume                     2086.37(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics
'CrystaMaker (CrystalMaker Software ltd., 2012)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6831
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.492
_diffrn_reflns_theta_min         3.169
_diffrn_source                   micro-source
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.345
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         2475
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0425
_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)+(0.0852P)²+0.7481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.934
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2434
_reflns_number_total             2475
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000001.cif
_cod_data_source_block           PCOD1000001
_cod_depositor_comments
;

2024-11-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C20 H24 F4 N6 O'
_cod_original_formula_weight         440.45
_cod_original_formula_moiety         '2(C10 H10 N3), 2(F2 H), H2 O'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        2086.36(5)
_cod_database_code               7233865
_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   0.662
_shelx_estimated_absorpt_t_max   0.908
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, 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
N2A N 0.58652(17) 0.0596(3) 0.28690(13) 0.0224(6) Uani 1 1 d . . . . .
H2NA H 0.6153 0.1122 0.2526 0.027 Uiso 1 1 calc R U . . .
N1A N 0.43932(17) 0.1165(3) 0.23447(15) 0.0253(6) Uani 1 1 d . . . . .
H1NA H 0.3766 0.1118 0.2391 0.030 Uiso 1 1 calc R U . . .
C1A C 0.4913(2) 0.0463(4) 0.28637(15) 0.0222(6) Uani 1 1 d . . . . .
C2A C 0.4451(2) -0.0369(4) 0.34182(18) 0.0241(7) Uani 1 1 d . . . . .
H2A H 0.3771 -0.0460 0.3431 0.029 Uiso 1 1 calc R U . . .
N3A N 0.56684(19) 0.2148(3) 0.16800(14) 0.0294(6) Uani 1 1 d . . . . .
C4A C 0.5992(2) -0.0881(4) 0.39228(18) 0.0287(7) Uani 1 1 d . . . . .
H4A H 0.6371 -0.1343 0.4283 0.034 Uiso 1 1 calc R U . . .
C6A C 0.4730(2) 0.1954(4) 0.17446(17) 0.0268(7) Uani 1 1 d . . . . .
C5A C 0.6407(2) -0.0054(4) 0.33865(19) 0.0283(7) Uani 1 1 d . . . . .
H5A H 0.7085 0.0072 0.3372 0.034 Uiso 1 1 calc R U . . .
C8A C 0.4428(3) 0.3292(5) 0.06659(19) 0.0395(9) Uani 1 1 d . . . . .
H8A H 0.4005 0.3691 0.0319 0.047 Uiso 1 1 calc R U . . .
C3A C 0.4992(3) -0.1037(3) 0.39336(18) 0.0280(6) Uani 1 1 d . . . . .
H3A H 0.4689 -0.1615 0.4305 0.034 Uiso 1 1 calc R U . . .
C7A C 0.4067(3) 0.2521(4) 0.12560(18) 0.0335(8) Uani 1 1 d . . . . .
H7A H 0.3397 0.2386 0.1325 0.040 Uiso 1 1 calc R U . . .
C9A C 0.5404(3) 0.3467(4) 0.05923(19) 0.0378(9) Uani 1 1 d . . . . .
H9A H 0.5665 0.3984 0.0192 0.045 Uiso 1 1 calc R U . . .
C10A C 0.5998(3) 0.2884(4) 0.11037(19) 0.0335(8) Uani 1 1 d . . . . .
H10A H 0.6672 0.3006 0.1047 0.040 Uiso 1 1 calc R U . . .
F1B F 0.74321(12) 0.5280(2) 0.23329(17) 0.0427(5) Uani 1 1 d . . . . .
N2B N 0.92467(18) 0.0608(3) 0.18600(15) 0.0265(6) Uani 1 1 d . . . . .
H2NB H 0.8978 0.1084 0.2222 0.032 Uiso 1 1 calc R U . . .
C1B C 1.0203(2) 0.0499(4) 0.18159(17) 0.0245(7) Uani 1 1 d . . . . .
C2B C 1.0652(2) -0.0262(4) 0.12478(17) 0.0271(7) Uani 1 1 d . . . . .
H2B H 1.1331 -0.0328 0.1218 0.033 Uiso 1 1 calc R U . . .
C10B C 0.9192(2) 0.2945(4) 0.36079(18) 0.0303(7) Uani 1 1 d . . . . .
H10B H 0.8522 0.3093 0.3674 0.036 Uiso 1 1 calc R U . . .
C9B C 0.9811(3) 0.3514(4) 0.41010(18) 0.0310(7) Uani 1 1 d . . . . .
H9B H 0.9573 0.4066 0.4501 0.037 Uiso 1 1 calc R U . . .
N1B N 1.07494(17) 0.1170(3) 0.23455(14) 0.0243(5) Uani 1 1 d . . . . .
H1NB H 1.1375 0.1081 0.2295 0.029 Uiso 1 1 calc R U . . .
C4B C 0.9090(3) -0.0788(4) 0.0786(2) 0.0364(8) Uani 1 1 d . . . . .
H4B H 0.8689 -0.1237 0.0436 0.044 Uiso 1 1 calc R U . . .
N3B N 0.95060(17) 0.2182(3) 0.30320(14) 0.0250(6) Uani 1 1 d . . . . .
C6B C 1.0449(2) 0.1947(3) 0.29326(16) 0.0227(6) Uani 1 1 d . . . . .
C5B C 0.8699(2) -0.0009(4) 0.13516(19) 0.0314(7) Uani 1 1 d . . . . .
H5B H 0.8021 0.0097 0.1384 0.038 Uiso 1 1 calc R U . . .
C8B C 1.0792(3) 0.3278(4) 0.40118(18) 0.0311(7) Uani 1 1 d . . . . .
H8B H 1.1231 0.3665 0.4351 0.037 Uiso 1 1 calc R U . . .
C7B C 1.1120(2) 0.2483(4) 0.34301(18) 0.0285(7) Uani 1 1 d . . . . .
H7B H 1.1787 0.2295 0.3363 0.034 Uiso 1 1 calc R U . . .
C3B C 1.0079(3) -0.0911(4) 0.07342(18) 0.0330(8) Uani 1 1 d . . . . .
H3B H 1.0362 -0.1441 0.0345 0.040 Uiso 1 1 calc R U . . .
F2B F 0.75700(12) 0.2305(3) 0.24572(19) 0.0625(9) Uani 1 1 d . . . . .
H1FB H 0.7516 0.3795 0.2395 0.094 Uiso 1 1 d R U . . .
O1 O 1.21959(19) -0.0833(4) 0.00601(16) 0.0492(7) Uani 1 1 d . . . . .
H1O H 1.2444 -0.1543 -0.0200 0.074 Uiso 1 1 d R U . . .
H2O H 1.2380 0.0206 -0.0062 0.074 Uiso 1 1 d R U . . .
F1A F 1.26046(15) 0.1003(3) 0.46059(17) 0.0537(6) Uani 1 1 d . . . . .
H1FA H 1.2703 -0.0470 0.4497 0.081 Uiso 1 1 d R U . . .
F2A F 1.28320(16) -0.1940(3) 0.43908(17) 0.0554(6) 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'
F F 0.0727 0.0534 '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'
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
C1A N2A C5A 122.2(3) . .
C1A N2A H2NA 118.9 . .
C5A N2A H2NA 118.9 . .
C1A N1A C6A 128.2(3) . .
C1A N1A H1NA 115.9 . .
C6A N1A H1NA 115.9 . .
N2A C1A N1A 120.5(3) . .
N2A C1A C2A 118.9(3) . .
N1A C1A C2A 120.6(3) . .
C3A C2A C1A 119.0(3) . .
C3A C2A H2A 120.5 . .
C1A C2A H2A 120.5 . .
C6A N3A C10A 117.8(3) . .
C5A C4A C3A 118.5(3) . .
C5A C4A H4A 120.8 . .
C3A C4A H4A 120.8 . .
N3A C6A C7A 123.6(3) . .
N3A C6A N1A 117.3(3) . .
C7A C6A N1A 119.1(3) . .
C4A C5A N2A 120.7(3) . .
C4A C5A H5A 119.6 . .
N2A C5A H5A 119.6 . .
C9A C8A C7A 119.1(3) . .
C9A C8A H8A 120.5 . .
C7A C8A H8A 120.5 . .
C2A C3A C4A 120.7(3) . .
C2A C3A H3A 119.7 . .
C4A C3A H3A 119.7 . .
C8A C7A C6A 117.5(3) . .
C8A C7A H7A 121.3 . .
C6A C7A H7A 121.3 . .
C10A C9A C8A 119.2(3) . .
C10A C9A H9A 120.4 . .
C8A C9A H9A 120.4 . .
N3A C10A C9A 122.9(3) . .
N3A C10A H10A 118.6 . .
C9A C10A H10A 118.6 . .
C1B N2B C5B 119.8(3) . .
C1B N2B H2NB 120.1 . .
C5B N2B H2NB 120.1 . .
N2B C1B N1B 118.4(3) . .
N2B C1B C2B 121.4(3) . .
N1B C1B C2B 120.1(3) . .
C3B C2B C1B 118.0(3) . .
C3B C2B H2B 121.0 . .
C1B C2B H2B 121.0 . .
N3B C10B C9B 121.7(3) . .
N3B C10B H10B 119.1 . .
C9B C10B H10B 119.1 . .
C10B C9B C8B 119.4(3) . .
C10B C9B H9B 120.3 . .
C8B C9B H9B 120.3 . .
C6B N1B C1B 128.7(2) . .
C6B N1B H1NB 115.6 . .
C1B N1B H1NB 115.6 . .
C5B C4B C3B 119.0(3) . .
C5B C4B H4B 120.5 . .
C3B C4B H4B 120.5 . .
C6B N3B C10B 120.0(3) . .
N3B C6B N1B 118.8(3) . .
N3B C6B C7B 120.7(3) . .
N1B C6B C7B 120.4(3) . .
N2B C5B C4B 121.7(3) . .
N2B C5B H5B 119.1 . .
C4B C5B H5B 119.1 . .
C7B C8B C9B 119.4(3) . .
C7B C8B H8B 120.3 . .
C9B C8B H8B 120.3 . .
C8B C7B C6B 118.8(3) . .
C8B C7B H7B 120.6 . .
C6B C7B H7B 120.6 . .
C2B C3B C4B 119.9(3) . .
C2B C3B H3B 120.0 . .
C4B C3B H3B 120.0 . .
H1O O1 H2O 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2A C1A 1.332(4) .
N2A C5A 1.359(4) .
N2A H2NA 0.8800 .
N1A C1A 1.359(4) .
N1A C6A 1.402(4) .
N1A H1NA 0.8800 .
C1A C2A 1.414(4) .
C2A C3A 1.361(5) .
C2A H2A 0.9500 .
N3A C6A 1.324(4) .
N3A C10A 1.343(4) .
C4A C5A 1.356(5) .
C4A C3A 1.399(5) .
C4A H4A 0.9500 .
C6A C7A 1.399(5) .
C5A H5A 0.9500 .
C8A C9A 1.376(6) .
C8A C7A 1.391(5) .
C8A H8A 0.9500 .
C3A H3A 0.9500 .
C7A H7A 0.9500 .
C9A C10A 1.374(5) .
C9A H9A 0.9500 .
C10A H10A 0.9500 .
F1B H1FB 1.1458 .
N2B C1B 1.339(4) .
N2B C5B 1.341(5) .
N2B H2NB 0.8800 .
C1B N1B 1.386(4) .
C1B C2B 1.403(5) .
C2B C3B 1.377(5) .
C2B H2B 0.9500 .
C10B N3B 1.343(4) .
C10B C9B 1.367(5) .
C10B H10B 0.9500 .
C9B C8B 1.391(5) .
C9B H9B 0.9500 .
N1B C6B 1.361(4) .
N1B H1NB 0.8800 .
C4B C5B 1.370(5) .
C4B C3B 1.387(6) .
C4B H4B 0.9500 .
N3B C6B 1.342(4) .
C6B C7B 1.412(4) .
C5B H5B 0.9500 .
C8B C7B 1.370(5) .
C8B H8B 0.9500 .
C7B H7B 0.9500 .
C3B H3B 0.9500 .
F2B H1FB 1.1471 .
O1 H1O 0.8210 .
O1 H2O 0.8672 .
F1A H1FA 1.1528 .
F2A H1FA 1.1555 .
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
F1B H1FB F2B 1.15 1.15 2.292(3) 177.9 . yes
F1A H1FA F2A 1.15 1.16 2.308(3) 177.9 . yes
N2A H2NA N3A 0.88 1.95 2.629(4) 132.3 . yes
N2B H2NB N3B 0.88 1.94 2.617(4) 132.6 . yes
