#------------------------------------------------------------------------------
#$Date: 2019-09-16 12:14:06 +0300 (Mon, 16 Sep 2019) $
#$Revision: 218316 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/38/7233870.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_7233870
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, C H Cl3, I'
_chemical_formula_sum            'C11 H11 Cl3 I N3'
_chemical_formula_weight         418.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.65379(12)
_cell_length_b                   14.07388(14)
_cell_length_c                   10.48437(10)
_cell_measurement_reflns_used    13420
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      32.4180
_cell_measurement_theta_min      2.4020
_cell_volume                     1572.03(3)
_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      290(2)
_diffrn_detector_area_resol_mean 16.0107
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0207
_diffrn_reflns_av_unetI/netI     0.0070
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34119
_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         29.493
_diffrn_reflns_theta_min         2.422
_diffrn_source                   micro-source
_exptl_absorpt_coefficient_mu    2.533
_exptl_absorpt_correction_T_max  0.545
_exptl_absorpt_correction_T_min  0.369
_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            yellow
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.153
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.513
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0536P)²+0.9274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2043
_reflns_number_total             2276
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            1000006.cif
_cod_data_source_block           PCOD1000006
_cod_database_code               7233870
_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   0.697
_shelx_estimated_absorpt_t_max   0.817
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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
I1 I 0.49128(2) 0.2500 0.21709(2) 0.05263(10) Uani 1 2 d S T P . .
Cl1 Cl 0.12858(14) 0.64827(9) 0.31023(12) 0.1237(4) Uani 1 1 d . . . . .
Cl2 Cl 0.34890(16) 0.7500 0.3786(3) 0.1474(7) Uani 1 2 d S T P . .
N1 N 0.4993(3) 0.4356(3) 0.4377(5) 0.0550(10) Uani 0.5 1 d . . P . .
H1 H 0.4996 0.3853 0.3912 0.066 Uiso 0.5 1 calc R U P A 1
C2 C 0.2764(2) 0.39836(18) 0.4675(2) 0.0609(5) Uani 1 1 d . . . . .
H2 H 0.2765 0.3456 0.4140 0.073 Uiso 1 1 calc R U . B 1
C3 C 0.1683(2) 0.4246(2) 0.5274(3) 0.0692(6) Uani 1 1 d . . . . .
H3 H 0.0952 0.3895 0.5159 0.083 Uiso 1 1 calc R U . . .
C4 C 0.1683(2) 0.5040(2) 0.6056(3) 0.0695(7) Uani 1 1 d . . . . .
H4 H 0.0953 0.5228 0.6471 0.083 Uiso 1 1 calc R U . . .
C5 C 0.2768(2) 0.55426(19) 0.6209(2) 0.0626(6) Uani 1 1 d . . . . .
H5 H 0.2773 0.6084 0.6718 0.075 Uiso 1 1 calc R U . C 1
C6 C 0.1867(5) 0.7500 0.3822(4) 0.0792(11) Uani 1 2 d S T P . .
H6 H 0.1599 0.7500 0.4716 0.095 Uiso 1 2 calc R U P . .
N2 N 0.3833(2) 0.52579(17) 0.5627(2) 0.0612(5) Uani 0.5 1 d . . P D 1
H2A H 0.4563 0.5549 0.5754 0.073 Uiso 0.25 1 d R U P D 1
C1 C 0.3838(2) 0.44835(17) 0.4850(2) 0.0604(5) Uani 0.5 1 d . . P D 1
C1B C 0.3833(2) 0.52579(17) 0.5627(2) 0.0612(5) Uani 0.5 1 d . . P D 2
N2B N 0.3838(2) 0.44835(17) 0.4850(2) 0.0604(5) Uani 0.5 1 d . . P D 2
H2B H 0.4561 0.4305 0.4489 0.072 Uiso 0.25 1 d R U P D 2
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'
Cl Cl 0.1484 0.1585 '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'
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 N2 142.2(3) . 5_666
C1 N1 H1 108.9 . .
N2 N1 H1 108.9 5_666 .
C1B N1 H2B 159.8 5_666 .
C1 C2 C3 120.7(2) . .
C1 C2 H2 119.7 . .
C3 C2 H2 119.7 . .
C2 C3 C4 119.4(2) . .
C2 C3 H3 120.3 . .
C4 C3 H3 120.3 . .
C5 C4 C3 119.2(2) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
N2 C5 C4 120.3(2) . .
N2 C5 H5 119.8 . .
C4 C5 H5 119.8 . .
Cl2 C6 Cl1 110.35(17) . 8_575
Cl2 C6 Cl1 110.35(17) . .
Cl1 C6 Cl1 111.5(3) 8_575 .
Cl2 C6 H6 108.2 . .
Cl1 C6 H6 108.2 8_575 .
Cl1 C6 H6 108.2 . .
C5 N2 C1 120.8(2) . .
C5 N2 N1 130.8(3) . 5_666
C1 N2 N1 108.3(2) . 5_666
C5 N2 H2A 122.0 . .
C1 N2 H2A 117.1 . .
N1 N2 H2A 9.8 5_666 .
N1 C1 C2 131.0(3) . .
N1 C1 N2 109.4(2) . .
C2 C1 N2 119.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C6 1.732(3) .
Cl2 C6 1.729(5) .
N1 C1 1.339(4) .
N1 C1B 1.364(4) 5_666
N1 N2 1.364(4) 5_666
N1 H1 0.8600 .
N1 H2B 0.4804 .
C2 C1 1.355(3) .
C2 C3 1.363(3) .
C2 H2 0.9300 .
C3 C4 1.387(4) .
C3 H3 0.9300 .
C4 C5 1.364(4) .
C4 H4 0.9300 .
C5 N2 1.350(3) .
C5 H5 0.9300 .
C6 Cl1 1.732(3) 8_575
C6 H6 0.9800 .
N2 C1 1.361(4) .
N2 N1 1.364(4) 5_666
N2 H2A 0.8896 .
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 I1 0.86 2.64 3.490(4) 170.5 . yes
