#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/37/2213754.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_2213754
loop_
_publ_author_name
'Jing-Cai Yao'
'Li Zhang'
'Li Qu'
'Cong Liu'
'Wei Wang'
_publ_section_title
;
 1,1'-(Butane-1,4-diyl)bis(imidazolium) bis(perchlorate)
;
_journal_coeditor_code           DN2176
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3029
_journal_page_last               o3029
_journal_paper_doi               10.1107/S1600536807024889
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C10 H16 N4 2+, 2Cl O4 -'
_chemical_formula_moiety         'C10 H16 N4 2+, 2(Cl O4 -)'
_chemical_formula_sum            'C10 H16 Cl2 N4 O8'
_chemical_formula_weight         391.17
_chemical_name_systematic
;
1,1'-(Butane-1,4-diyl)bis(imidazolium) 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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.273(2)
_cell_angle_beta                 96.074(2)
_cell_angle_gamma                95.853(2)
_cell_formula_units_Z            1
_cell_length_a                   5.5570(10)
_cell_length_b                   7.6280(14)
_cell_length_c                   9.6139(17)
_cell_measurement_reflns_used    2535
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.20
_cell_measurement_theta_min      2.70
_cell_volume                     400.94(13)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            2949
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.454
_exptl_absorpt_correction_T_max  0.8493
_exptl_absorpt_correction_T_min  0.8126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             202
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.354
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1475
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.141
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0352
_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)+(0.0424P)²+0.2168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0955
_reflns_number_gt                1396
_reflns_number_total             1475
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2176.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        400.93(13)
_cod_database_code               2213754
_cod_database_fobs_code          2213754
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_refinement_flags
_atom_site_occupancy
Cl Cl1 0.08600(9) 0.78746(6) 0.73164(5) 0.03864(19) Uani d . 1
O O1 0.0172(4) 0.8598(2) 0.86226(18) 0.0652(5) Uani d . 1
O O2 -0.0516(4) 0.6196(2) 0.6882(2) 0.0732(6) Uani d . 1
O O3 0.0428(4) 0.9096(2) 0.62750(18) 0.0639(5) Uani d . 1
O O4 0.3407(3) 0.7663(3) 0.74746(18) 0.0616(5) Uani d . 1
N N1 0.5280(3) 0.7551(2) 0.21145(17) 0.0378(4) Uani d . 1
N N2 0.3307(4) 0.8272(3) 0.3850(2) 0.0569(5) Uani d . 1
H H2 0.2264 0.8723 0.4335 0.068 Uiso calc R 1
C C1 0.5040(5) 0.7278(3) 0.4347(2) 0.0488(5) Uani d . 1
H H1 0.5315 0.6969 0.5259 0.059 Uiso calc R 1
C C2 0.6280(4) 0.6827(3) 0.3267(2) 0.0435(5) Uani d . 1
H H2A 0.7579 0.6149 0.3295 0.052 Uiso calc R 1
C C3 0.3476(4) 0.8438(3) 0.2504(3) 0.0502(6) Uani d . 1
H H3 0.2504 0.9066 0.1929 0.060 Uiso calc R 1
C C4 0.6119(5) 0.7460(3) 0.0705(2) 0.0499(6) Uani d . 1
H H4A 0.7726 0.8112 0.0768 0.060 Uiso calc R 1
H H4B 0.5024 0.8024 0.0079 0.060 Uiso calc R 1
C C5 0.6226(4) 0.5566(3) 0.0085(2) 0.0431(5) Uani d . 1
H H5A 0.7381 0.5024 0.0690 0.052 Uiso calc R 1
H H5B 0.6820 0.5587 -0.0827 0.052 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0467(3) 0.0361(3) 0.0359(3) 0.0107(2) 0.0101(2) 0.00608(19)
O1 0.0902(14) 0.0611(11) 0.0498(10) 0.0131(10) 0.0330(9) 0.0013(8)
O2 0.0756(13) 0.0462(10) 0.0915(15) -0.0008(9) 0.0017(10) -0.0088(9)
O3 0.0812(13) 0.0673(11) 0.0549(10) 0.0354(10) 0.0171(9) 0.0279(9)
O4 0.0482(10) 0.0834(13) 0.0590(11) 0.0187(9) 0.0095(8) 0.0211(9)
N1 0.0487(10) 0.0310(8) 0.0332(9) 0.0046(7) 0.0051(7) -0.0002(6)
N2 0.0592(13) 0.0520(12) 0.0606(13) 0.0085(10) 0.0234(10) -0.0106(10)
C1 0.0647(15) 0.0474(12) 0.0339(11) 0.0038(11) 0.0096(10) 0.0001(9)
C2 0.0515(12) 0.0423(11) 0.0379(11) 0.0122(9) 0.0040(9) 0.0035(9)
C3 0.0490(13) 0.0399(11) 0.0610(15) 0.0126(10) 0.0006(10) 0.0012(10)
C4 0.0732(16) 0.0398(11) 0.0352(11) -0.0069(10) 0.0129(10) 0.0034(9)
C5 0.0541(13) 0.0428(11) 0.0326(10) -0.0015(9) 0.0155(9) 0.0002(8)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
O2 Cl1 O1 . . 109.83(12)
O2 Cl1 O4 . . 109.42(12)
O1 Cl1 O4 . . 109.85(12)
O2 Cl1 O3 . . 110.53(13)
O1 Cl1 O3 . . 108.80(11)
O4 Cl1 O3 . . 108.39(11)
C3 N1 C2 . . 108.00(18)
C3 N1 C4 . . 125.27(19)
C2 N1 C4 . . 126.65(19)
C3 N2 C1 . . 109.38(19)
C3 N2 H2 . . 125.3
C1 N2 H2 . . 125.3
C2 C1 N2 . . 106.8(2)
C2 C1 H1 . . 126.6
N2 C1 H1 . . 126.6
C1 C2 N1 . . 107.6(2)
C1 C2 H2A . . 126.2
N1 C2 H2A . . 126.2
N2 C3 N1 . . 108.2(2)
N2 C3 H3 . . 125.9
N1 C3 H3 . . 125.9
N1 C4 C5 . . 112.46(17)
N1 C4 H4A . . 109.1
C5 C4 H4A . . 109.1
N1 C4 H4B . . 109.1
C5 C4 H4B . . 109.1
H4A C4 H4B . . 107.8
C4 C5 C5 . 2_665 113.3(2)
C4 C5 H5A . . 108.9
C5 C5 H5A 2_665 . 108.9
C4 C5 H5B . . 108.9
C5 C5 H5B 2_665 . 108.9
H5A C5 H5B . . 107.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 O2 . 1.4262(19)
Cl1 O1 . 1.4301(17)
Cl1 O4 . 1.4346(18)
Cl1 O3 . 1.4471(17)
N1 C3 . 1.332(3)
N1 C2 . 1.373(3)
N1 C4 . 1.478(3)
N2 C3 . 1.325(3)
N2 C1 . 1.360(3)
N2 H2 . 0.8600
C1 C2 . 1.343(3)
C1 H1 . 0.9300
C2 H2A . 0.9300
C3 H3 . 0.9300
C4 C5 . 1.520(3)
C4 H4A . 0.9700
C4 H4B . 0.9700
C5 C5 2_665 1.522(4)
C5 H5A . 0.9700
C5 H5B . 0.9700
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
N2 H2 O3 . 0.86 2.23 3.019(3) 152.8
N2 H2 O3 2_576 0.86 2.42 3.032(3) 128.7
C1 H1 O4 . 0.93 2.51 3.228(3) 133.7
C3 H3 O1 2_576 0.93 2.49 3.363(3) 156.0
C2 H2A O2 2_666 0.93 2.55 3.464(3) 168.6
C4 H4B O4 1_554 0.97 2.55 3.329(3) 137.5
