#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/59/2015966.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2015966
loop_
_publ_author_name
'Ghazzali, Mohamed'
'Langer, Vratislav'
'Öhrström, Lars'
'Abu-Youssef, Morsy'
_publ_section_title
;
 4,4'-(Azinodimethylene)dipyridinium bis(tetrafluoroborate) and
 4-[(4-pyridylmethylene)hydrazonomethyl]pyridinium perchlorate: two
 different hydrogen-bonding motifs
;
_journal_coeditor_code           SK3115
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o312
_journal_page_last               o314
_journal_paper_doi               10.1107/S0108270107015764
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C12 H11 N4 + , Cl O4 -'
_chemical_formula_moiety         'C12 H11 N4 + , Cl O4 -'
_chemical_formula_sum            'C12 H11 Cl N4 O4'
_chemical_formula_weight         310.70
_chemical_name_systematic
;
4-[4-pyridylmethylene)hydrazonomethyl]pyridinium perchlorate
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.0896(6)
_cell_length_b                   11.5525(5)
_cell_length_c                   7.8694(3)
_cell_measurement_reflns_used    5650
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      3.22
_cell_volume                     1371.81(10)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        'SAINT and SADABS (Sheldrick, 2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2003)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18851
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.9763
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.210
_refine_ls_abs_structure_details 'Flack (1983), with 1594 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3440
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0322
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0484P)²+0.1706P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                2994
_reflns_number_total             3440
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk3115.cif
_cod_data_source_block           II
_cod_database_code               2015966
_cod_database_fobs_code          2015966
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cl Cl1 0.98221(3) 0.76602(3) 0.00534(6) 0.02777(11) Uani d . 1
O O1 0.92927(10) 0.69864(14) 0.12131(19) 0.0396(4) Uani d . 1
O O2 1.01859(10) 0.69249(14) -0.1247(2) 0.0428(4) Uani d . 1
O O3 0.92716(9) 0.85251(13) -0.0748(2) 0.0403(4) Uani d . 1
O O4 1.05271(10) 0.82178(15) 0.0958(2) 0.0440(4) Uani d . 1
N N1A 0.81434(11) 0.08944(13) 0.1570(2) 0.0262(3) Uani d . 1
C C1A 0.87944(12) 0.04458(16) 0.2366(2) 0.0237(4) Uani d . 1
H H1A 0.9372 0.0759 0.2235 0.028 Uiso calc R 1
C C2A 0.86515(12) -0.05595(15) 0.3491(2) 0.0221(4) Uani d . 1
C C3A 0.93832(12) -0.10634(15) 0.4283(2) 0.0238(4) Uani d . 1
H H3A 0.9959 -0.0748 0.4126 0.029 Uiso calc R 1
C C4A 0.92612(11) -0.20199(15) 0.5293(2) 0.0244(4) Uani d . 1
H H4A 0.9754 -0.2365 0.5848 0.029 Uiso calc R 1
N N5A 0.84507(10) -0.24675(12) 0.5495(2) 0.0243(3) Uani d . 1
H H5A 0.8387 -0.3095 0.6117 0.029 Uiso calc R 1
C C6A 0.77331(12) -0.19892(15) 0.4779(2) 0.0261(4) Uani d . 1
H H6A 0.7166 -0.2320 0.4972 0.031 Uiso calc R 1
C C7A 0.78106(12) -0.10232(15) 0.3766(2) 0.0239(4) Uani d . 1
H H7A 0.7302 -0.0680 0.3265 0.029 Uiso calc R 1
N N1B 0.84225(10) 0.18383(12) 0.0567(2) 0.0254(3) Uani d . 1
C C1B 0.77652(11) 0.23963(14) -0.0032(3) 0.0238(3) Uani d . 1
H H1B 0.7179 0.2126 0.0158 0.029 Uiso calc R 1
C C2B 0.79149(12) 0.34610(15) -0.1022(2) 0.0233(4) Uani d . 1
C C3B 0.71989(12) 0.41495(16) -0.1477(3) 0.0269(4) Uani d . 1
H H3B 0.6611 0.3915 -0.1215 0.032 Uiso calc R 1
C C4B 0.73543(14) 0.51879(15) -0.2322(3) 0.0289(4) Uani d . 1
H H4B 0.6862 0.5657 -0.2624 0.035 Uiso calc R 1
N N5B 0.81684(11) 0.55534(14) -0.2726(2) 0.0294(4) Uani d . 1
C C6B 0.88550(14) 0.48630(17) -0.2334(3) 0.0338(5) Uani d . 1
H H6B 0.9435 0.5103 -0.2647 0.041 Uiso calc R 1
C C7B 0.87559(12) 0.38182(16) -0.1495(3) 0.0306(4) Uani d . 1
H H7B 0.9258 0.3352 -0.1247 0.037 Uiso calc R 1
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'
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'
Cl Cl 0.1484 0.1585 '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
O4 Cl1 O2 109.61(10)
O4 Cl1 O1 109.86(10)
O2 Cl1 O1 110.05(9)
O4 Cl1 O3 109.45(10)
O2 Cl1 O3 108.50(9)
O1 Cl1 O3 109.35(9)
C1A N1A N1B 111.04(15)
N1A C1A C2A 120.12(16)
N1A C1A H1A 119.9
C2A C1A H1A 119.9
C7A C2A C3A 119.37(16)
C7A C2A C1A 121.90(16)
C3A C2A C1A 118.73(16)
C4A C3A C2A 119.22(16)
C4A C3A H3A 120.4
C2A C3A H3A 120.4
N5A C4A C3A 120.17(16)
N5A C4A H4A 119.9
C3A C4A H4A 119.9
C6A N5A C4A 121.98(15)
C6A N5A H5A 119.0
C4A N5A H5A 119.0
N5A C6A C7A 120.61(16)
N5A C6A H6A 119.7
C7A C6A H6A 119.7
C6A C7A C2A 118.61(16)
C6A C7A H7A 120.7
C2A C7A H7A 120.7
C1B N1B N1A 111.48(15)
N1B C1B C2B 119.93(15)
N1B C1B H1B 120.0
C2B C1B H1B 120.0
C7B C2B C3B 118.22(16)
C7B C2B C1B 122.09(16)
C3B C2B C1B 119.68(16)
C4B C3B C2B 119.07(17)
C4B C3B H3B 120.5
C2B C3B H3B 120.5
N5B C4B C3B 122.72(18)
N5B C4B H4B 118.6
C3B C4B H4B 118.6
C4B N5B C6B 117.81(16)
N5B C6B C7B 122.96(19)
N5B C6B H6B 118.5
C7B C6B H6B 118.5
C6B C7B C2B 119.14(18)
C6B C7B H7B 120.4
C2B C7B H7B 120.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 O4 1.4330(15)
Cl1 O2 1.4386(16)
Cl1 O1 1.4412(15)
Cl1 O3 1.4444(15)
N1A C1A 1.275(2)
N1A N1B 1.410(2)
C1A C2A 1.476(3)
C1A H1A 0.9500
C2A C7A 1.394(2)
C2A C3A 1.395(2)
C3A C4A 1.373(3)
C3A H3A 0.9500
C4A N5A 1.337(2)
C4A H4A 0.9500
N5A C6A 1.340(2)
N5A H5A 0.8800
C6A C7A 1.376(3)
C6A H6A 0.9500
C7A H7A 0.9500
N1B C1B 1.273(2)
C1B C2B 1.473(2)
C1B H1B 0.9500
C2B C7B 1.385(3)
C2B C3B 1.388(2)
C3B C4B 1.392(3)
C3B H3B 0.9500
C4B N5B 1.337(3)
C4B H4B 0.9500
N5B C6B 1.343(3)
C6B C7B 1.384(3)
C6B H6B 0.9500
C7B H7B 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N5A H5A N5B 1_546 0.88 1.84 2.715(2) 174 y
C3B H3B O2 3_465 0.95 2.36 3.286(2) 165 ?
C4A H4A O2 1_546 0.95 2.51 3.294(2) 139 ?
C4B H4B O1 4_654 0.95 2.50 3.438(2) 171 ?
C6A H6A O1 4_645 0.95 2.54 3.467(2) 166 ?
C6A H6A O3 4_645 0.95 2.44 3.111(2) 127 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
N1B N1A C1A C2A -179.83(16)
N1A C1A C2A C7A -2.2(3)
N1A C1A C2A C3A 177.12(18)
C7A C2A C3A C4A 1.2(3)
C1A C2A C3A C4A -178.10(16)
C2A C3A C4A N5A 0.7(3)
C3A C4A N5A C6A -2.1(3)
C4A N5A C6A C7A 1.5(3)
N5A C6A C7A C2A 0.5(3)
C3A C2A C7A C6A -1.8(3)
C1A C2A C7A C6A 177.48(17)
C1A N1A N1B C1B -170.36(17)
N1A N1B C1B C2B 175.91(17)
N1B C1B C2B C7B 7.4(3)
N1B C1B C2B C3B -171.35(19)
C7B C2B C3B C4B -2.6(3)
C1B C2B C3B C4B 176.15(17)
C2B C3B C4B N5B 0.3(3)
C3B C4B N5B C6B 2.0(3)
C4B N5B C6B C7B -1.9(3)
N5B C6B C7B C2B -0.4(3)
C3B C2B C7B C6B 2.7(3)
C1B C2B C7B C6B -176.08(18)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21180662
