#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/94/2019402.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_2019402
loop_
_publ_author_name
'Gholizadeh, Mostafa'
'Pourayoubi, Mehrdad'
'Farimaneh, Masoumeh'
'Tarahhomi, Atekeh'
'Dušek, Michal'
'Eigner, Václav'
_publ_section_title
;
 Hirshfeld surface analysis of the 1,1'-(ethane-1,2-diyl)dipyridinium
 dication in two new salts: perchlorate and peroxodisulfate
;
_journal_coeditor_code           LG3130
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              230
_journal_page_last               235
_journal_paper_doi               10.1107/S2053229614000576
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C12 H14 N2 2+ , 2Cl O4 -'
_chemical_formula_moiety         'C12 H14 N2 2+, 2(Cl O4 -)'
_chemical_formula_sum            'C12 H14 Cl2 N2 O8'
_chemical_formula_weight         385.15
_chemical_name_systematic
;
1,1'-(Ethane-1,2-diyl)dipyridinium bis(perchlorate)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                97.858(4)
_cell_angle_beta                 95.503(4)
_cell_angle_gamma                100.655(4)
_cell_formula_units_Z            1
_cell_length_a                   6.0687(3)
_cell_length_b                   6.7263(4)
_cell_length_c                   9.8005(3)
_cell_measurement_reflns_used    4357
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      29.26
_cell_measurement_theta_min      3.11
_cell_volume                     386.44(3)
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2010)'
_computing_data_collection       'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2010)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material
;
JANA2006 (Petříček et al., 2006), enCIFer (Allen,
et al., 2004) and PLATON (Spek, 2009)
;
_computing_structure_refinement
'JANA2006 (Petříček et al., 2006)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.89
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type
'Agilent Xcalibur Gemini Ultra diffractometer with Atlas detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0186
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6178
_diffrn_reflns_theta_full        27.9
_diffrn_reflns_theta_max         29.32
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.466
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.6545
_exptl_crystal_description       prism
_exptl_crystal_F_000             198
_exptl_crystal_size_max          0.569
_exptl_crystal_size_mid          0.314
_exptl_crystal_size_min          0.172
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.33
_refine_ls_extinction_coef       16E2(4)
_refine_ls_extinction_method
;
B--C type 1 Gaussian isotropic (Becker & Coppens, 1974)
Becker, P. J. & Coppens, P. (1974). Acta Cryst. A30,
129--147.
;
_refine_ls_goodness_of_fit_ref   1.79
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_constraints    28
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1904
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.0104
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/(σ²(I)+0.0016I²)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1039
_reflns_number_gt                1717
_reflns_number_total             1904
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            lg3130sup1.cif
_cod_data_source_block           I
_cod_database_code               2019402
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
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_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 0.51205(6) 0.20569(6) 0.21529(3) 0.01404(14) Uani d 1 2
O O1 0.75374(18) 0.23345(19) 0.24274(12) 0.0210(4) Uani d 1 2
O O2 0.45627(19) 0.32895(18) 0.11147(11) 0.0195(4) Uani d 1 2
O O3 0.4230(2) 0.2722(2) 0.34055(12) 0.0296(5) Uani d 1 2
O O4 0.4163(2) -0.0060(2) 0.16526(14) 0.0328(5) Uani d 1 2
N N2 0.0120(2) 0.66514(19) 0.17194(12) 0.0120(4) Uani d 1 2
C C6 -0.2013(3) 0.7874(2) 0.34153(16) 0.0170(5) Uani d 1 2
C C4 0.1380(3) 0.6737(2) 0.40854(15) 0.0163(5) Uani d 1 2
C C5 -0.0477(3) 0.7514(2) 0.44444(15) 0.0167(5) Uani d 1 2
C C1 0.0473(2) 0.6135(2) 0.02463(14) 0.0141(5) Uani d 1 2
C C3 0.1645(3) 0.6299(2) 0.27022(15) 0.0145(5) Uani d 1 2
C C7 -0.1676(3) 0.7436(2) 0.20407(15) 0.0148(5) Uani d 1 2
H H1C6 -0.330164 0.842353 0.365405 0.0204 Uiso d 1 2
H H1C4 0.247221 0.650526 0.479091 0.0195 Uiso d 1 2
H H1C5 -0.070031 0.780266 0.540231 0.0201 Uiso d 1 2
H H1C1 0.206125 0.642718 0.016718 0.017 Uiso d 1 2
H H2C1 -0.02975 0.692644 -0.030912 0.017 Uiso d 1 2
H H1C3 0.291729 0.574231 0.243952 0.0174 Uiso d 1 2
H H1C7 -0.272253 0.769263 0.13189 0.0178 Uiso d 1 2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Cl 0.1484 0.1585 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cl1 O2 . . 109.06(7) yes
O1 Cl1 O3 . . 109.45(7) yes
O1 Cl1 O4 . . 109.70(8) yes
O2 Cl1 O3 . . 108.85(8) yes
O2 Cl1 O4 . . 109.68(7) yes
O3 Cl1 O4 . . 110.09(8) yes
C1 N2 C3 . . 117.85(13) yes
C1 N2 C7 . . 120.22(12) yes
C3 N2 C7 . . 121.93(13) yes
C5 C6 C7 . . 119.46(16) ?
C5 C6 H1C6 . . 120.27 ?
C7 C6 H1C6 . . 120.27 ?
C5 C4 C3 . . 119.21(15) ?
C5 C4 H1C4 . . 120.4 ?
C3 C4 H1C4 . . 120.4 ?
C6 C5 C4 . . 119.62(14) ?
C6 C5 H1C5 . . 120.19 ?
C4 C5 H1C5 . . 120.19 ?
N2 C1 C1 . 2_565 108.98(12) ?
N2 C1 H1C1 . . 109.47 ?
N2 C1 H2C1 . . 109.47 ?
C1 C1 H1C1 2_565 . 109.47 ?
C1 C1 H2C1 2_565 . 109.47 ?
H1C1 C1 H2C1 . . 109.95 ?
N2 C3 C4 . . 120.04(15) ?
N2 C3 H1C3 . . 119.98 ?
C4 C3 H1C3 . . 119.98 ?
N2 C7 C6 . . 119.73(14) ?
N2 C7 H1C7 . . 120.14 ?
C6 C7 H1C7 . . 120.14 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 O1 . 1.4381(12) yes
Cl1 O2 . 1.4510(13) yes
Cl1 O3 . 1.4374(13) yes
Cl1 O4 . 1.4332(13) yes
N2 C1 . 1.4835(18) yes
N2 C3 . 1.347(2) yes
N2 C7 . 1.341(2) yes
C6 C5 . 1.383(2) ?
C6 C7 . 1.382(2) ?
C6 H1C6 . 0.96 ?
C4 C5 . 1.382(2) ?
C4 C3 . 1.379(2) ?
C4 H1C4 . 0.96 ?
C5 H1C5 . 0.96 ?
C1 C1 2_565 1.5211(19) ?
C1 H1C1 . 0.96 ?
C1 H2C1 . 0.96 ?
C3 H1C3 . 0.96 ?
C7 H1C7 . 0.96 ?
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
C3 H1C3 O2 . 0.96 2.38 3.263(2) 152 yes
C7 H1C7 O2 2_565 0.96 2.48 3.3322(18) 148 yes
C1 H2C1 O2 2_565 0.96 2.60 3.326(2) 132 yes
C3 H1C3 O3 . 0.96 2.58 3.220(2) 125 yes
C4 H1C4 O3 2_666 0.96 2.47 3.3792(19) 159 yes
C1 H1C1 O2 2_665 0.96 2.50 3.3888(19) 155 yes
C3 . O4 1_565 . . 3.000(2) . yes
N2 . O4 1_565 . . 2.997(2) . yes
C1 H1C1 O4 1_565 0.96 2.63 3.129(2) 113 yes
C5 . C5 1_576 . . 3.297(2) . yes
C5 H1C5 O3 2_566 0.96 2.53 3.245(2) 132 yes
C5 . C4 2_566 . . 3.354(2) . yes
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_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 N2 C1 C1 2_565 83.48(15) yes
C7 N2 C1 C1 2_565 -96.28(15) yes
C4 C3 N2 C1 . -179.44(13) yes
C6 C7 N2 C1 . 178.73(13) yes
