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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/7/23/38/7233868.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_7233868
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, I, H2 O'
_chemical_formula_sum            'C10 H12 I N3 O'
_chemical_formula_weight         317.13
_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                104.349(2)
_cell_angle_beta                 108.232(3)
_cell_angle_gamma                90.833(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3741(5)
_cell_length_b                   8.9009(6)
_cell_length_c                   9.5009(6)
_cell_measurement_reflns_used    9759
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      40.29
_cell_measurement_theta_min      3.09
_cell_volume                     570.94(7)
_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      100(2)
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device
'62mm x 62mm CCD camera on three-circle goniostat'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_radiation_monochromator  'flat graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23341
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         40.310
_diffrn_reflns_theta_min         2.341
_exptl_absorpt_coefficient_mu    2.783
_exptl_absorpt_correction_T_max  0.7135
_exptl_absorpt_correction_T_min  0.4580
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008).
Additional spherical absorption correction applied with mu*r =  0.0000
Lambda/2 correction factor = 0.0015'
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.845
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.502
_exptl_crystal_size_mid          0.417
_exptl_crystal_size_min          0.226
_refine_diff_density_max         1.501
_refine_diff_density_min         -1.498
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         7046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.0209
_refine_ls_R_factor_gt           0.0194
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0250P)²+0.1085P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0510
_refine_ls_wR_factor_ref         0.0518
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6708
_reflns_number_total             7046
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000004.cif
_cod_data_source_block           PCOD1000004
_cod_database_code               7233868
_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   0.336
_shelx_estimated_absorpt_t_max   0.572
_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 0.19792(12) 0.13971(9) -0.02879(9) 0.01412(11) Uani 1 1 d . . . . .
H1N H 0.221(3) 0.124(2) 0.070(2) 0.027(5) Uiso 1 1 d . . . . .
N2 N 0.29034(12) -0.11367(9) -0.09311(9) 0.01464(11) Uani 1 1 d . . . . .
H2N H 0.300(3) -0.189(2) -0.163(3) 0.032(5) Uiso 1 1 d . . . . .
N3 N 0.29733(12) -0.03834(9) 0.16239(9) 0.01496(12) Uani 1 1 d . . . . .
C1 C 0.13855(15) 0.27382(11) -0.06437(11) 0.01731(14) Uani 1 1 d . . . . .
H1 H 0.1169 0.3565 0.0118 0.021 Uiso 1 1 calc R U . . .
C2 C 0.10993(16) 0.29050(12) -0.20853(12) 0.01943(15) Uani 1 1 d . . . . .
H2 H 0.0696 0.3842 -0.2336 0.023 Uiso 1 1 calc R U . . .
C3 C 0.14165(16) 0.16517(13) -0.31923(11) 0.01925(15) Uani 1 1 d . . . . .
H3 H 0.1226 0.1745 -0.4202 0.023 Uiso 1 1 calc R U . . .
C4 C 0.19958(15) 0.03008(11) -0.28286(10) 0.01672(14) Uani 1 1 d . . . . .
H4 H 0.2194 -0.0545 -0.3583 0.020 Uiso 1 1 calc R U . . .
C5 C 0.22950(13) 0.01785(10) -0.13185(9) 0.01333(12) Uani 1 1 d . . . . .
C6 C 0.31674(13) -0.14907(10) 0.04610(10) 0.01325(12) Uani 1 1 d . . . . .
C7 C 0.36411(15) -0.29887(11) 0.05758(11) 0.01701(14) Uani 1 1 d . . . . .
H7 H 0.3743 -0.3757 -0.0283 0.020 Uiso 1 1 calc R U . . .
C8 C 0.39533(16) -0.33070(12) 0.19811(13) 0.01975(16) Uani 1 1 d . . . . .
H8 H 0.4292 -0.4303 0.2108 0.024 Uiso 1 1 calc R U . . .
C9 C 0.37679(16) -0.21548(13) 0.32121(12) 0.01958(15) Uani 1 1 d . . . . .
H9 H 0.3978 -0.2350 0.4187 0.023 Uiso 1 1 calc R U . . .
C10 C 0.32722(15) -0.07240(12) 0.29794(11) 0.01758(14) Uani 1 1 d . . . . .
H10 H 0.3135 0.0058 0.3815 0.021 Uiso 1 1 calc R U . . .
O1S O 0.62552(14) 0.33360(11) 0.31892(11) 0.02822(18) Uani 1 1 d . . . . .
H1O H 0.5202 0.3341 0.3356 0.042 Uiso 1 1 d R U . . .
H1P H 0.7142 0.3971 0.3927 0.042 Uiso 1 1 d R U . . .
I1 I 0.16168(2) 0.35160(2) 0.34953(2) 0.01533(2) 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 0.0033 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'
I I -0.4742 1.8119 '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'
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
C5 N1 C1 122.59(8) . .
C5 N1 H1N 114.4(12) . .
C1 N1 H1N 123.1(12) . .
C5 N2 C6 127.76(8) . .
C5 N2 H2N 117.7(15) . .
C6 N2 H2N 114.0(15) . .
C6 N3 C10 117.84(8) . .
N1 C1 C2 120.56(9) . .
N1 C1 H1 119.7 . .
C2 C1 H1 119.7 . .
C1 C2 C3 118.32(9) . .
C1 C2 H2 120.8 . .
C3 C2 H2 120.8 . .
C4 C3 C2 120.73(9) . .
C4 C3 H3 119.6 . .
C2 C3 H3 119.6 . .
C3 C4 C5 119.26(9) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
N1 C5 N2 121.42(8) . .
N1 C5 C4 118.53(8) . .
N2 C5 C4 120.05(8) . .
N3 C6 N2 118.16(8) . .
N3 C6 C7 123.33(8) . .
N2 C6 C7 118.50(8) . .
C8 C7 C6 117.75(9) . .
C8 C7 H7 121.1 . .
C6 C7 H7 121.1 . .
C7 C8 C9 119.52(9) . .
C7 C8 H8 120.2 . .
C9 C8 H8 120.2 . .
C10 C9 C8 118.40(9) . .
C10 C9 H9 120.8 . .
C8 C9 H9 120.8 . .
N3 C10 C9 123.14(9) . .
N3 C10 H10 118.4 . .
C9 C10 H10 118.4 . .
H1O O1S H1P 112.2 . .
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
N1 C5 1.3466(12) . yes
N1 C1 1.3614(12) . yes
N1 H1N 0.95(2) . yes
N2 C5 1.3538(12) . yes
N2 C6 1.3906(12) . yes
N2 H2N 0.84(2) . ?
N3 C6 1.3326(12) . yes
N3 C10 1.3479(12) . yes
C1 C2 1.3651(14) . ?
C1 H1 0.9500 . ?
C2 C3 1.4090(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.3697(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.4139(12) . ?
C4 H4 0.9500 . ?
C6 C7 1.4049(13) . ?
C7 C8 1.3830(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.3957(16) . ?
C8 H8 0.9500 . ?
C9 C10 1.3809(14) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
O1S H1O 0.8393 . ?
O1S H1P 0.8626 . ?
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 N3 0.95(2) 1.88(2) 2.6412(11) 136.0(17) . yes
N1 H1N I1 0.95(2) 3.07(2) 3.7153(8) 126.8(15) . yes
N2 H2N O1S 0.84(2) 1.93(2) 2.7580(12) 167(2) 2_655 yes
O1S H1O I1 0.84 2.69 3.5249(10) 171.1 . yes
O1S H1P I1 0.86 3.47 3.8705(10) 111.7 1_655 yes
O1S H1P I1 0.86 2.77 3.5553(9) 152.4 2_666 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168338811
