#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/56/7105610.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_7105610
loop_
_publ_author_name
'Drab, David M.'
'Shamshina, Julia L.'
'Smiglak, Marcin'
'Hines, C. Corey'
'Cordes, David B.'
'Rogers, Robin D.'
_publ_section_title
;
 A general design platform for ionic liquid ions based on bridged
 multi-heterocycles with flexible symmetry and charge
;
_journal_issue                   20
_journal_name_full               'Chemical Communications'
_journal_page_first              3544
_journal_paper_doi               10.1039/c002861d
_journal_volume                  46
_journal_year                    2010
_chemical_formula_sum            'C6 H9 Cl N6'
_chemical_formula_weight         200.64
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.339(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.128(5)
_cell_length_b                   5.2371(9)
_cell_length_c                   12.583(2)
_cell_measurement_reflns_used    3395
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.87
_cell_volume                     1867.7(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0288
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5782
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_correction_T_min  0.8502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorles
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0421
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0666P)²+0.8013P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                1863
_reflns_number_total             2210
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c002861d.txt
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7105610
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.568383(15) 0.91922(8) 0.39673(3) 0.04381(17) Uani 1 1 d . . .
N1 N 0.58337(5) 0.5680(3) 0.64232(12) 0.0466(4) Uani 1 1 d . . .
N2 N 0.64664(5) 0.4883(3) 0.58937(12) 0.0400(3) Uani 1 1 d . . .
N3 N 0.66496(6) 0.7086(3) 0.39395(12) 0.0441(4) Uani 1 1 d . . .
H3N H 0.6315(9) 0.770(5) 0.395(2) 0.074(7) Uiso 1 1 d . . .
N4 N 0.68779(6) 0.8139(3) 0.32346(13) 0.0524(4) Uani 1 1 d . . .
N5 N 0.72771(6) 0.6967(4) 0.33713(14) 0.0528(4) Uani 1 1 d . . .
N6 N 0.73173(6) 0.5152(3) 0.41606(13) 0.0505(4) Uani 1 1 d . . .
C1 C 0.53464(9) 0.5573(7) 0.6553(2) 0.0858(9) Uani 1 1 d . . .
H1A H 0.5202 0.4011 0.6245 0.129 Uiso 1 1 calc R . .
H1B H 0.5172 0.6998 0.6183 0.129 Uiso 1 1 calc R . .
H1C H 0.5346 0.5642 0.7315 0.129 Uiso 1 1 calc R . .
C2 C 0.60199(7) 0.4187(4) 0.57919(15) 0.0441(4) Uani 1 1 d . . .
H2A H 0.5867(7) 0.298(4) 0.5326(17) 0.048(5) Uiso 1 1 d . . .
C3 C 0.65633(7) 0.6910(4) 0.66094(14) 0.0440(4) Uani 1 1 d . . .
H3A H 0.6882(9) 0.762(5) 0.685(2) 0.067(7) Uiso 1 1 d . . .
C4 C 0.61654(7) 0.7405(4) 0.69305(15) 0.0473(4) Uani 1 1 d . . .
H4A H 0.6101(9) 0.869(5) 0.746(2) 0.074(7) Uiso 1 1 d . . .
C5 C 0.68005(9) 0.3632(4) 0.5358(2) 0.0551(5) Uani 1 1 d . . .
H5A H 0.6644(10) 0.209(6) 0.500(2) 0.085(9) Uiso 1 1 d . . .
H5B H 0.7092(11) 0.305(6) 0.587(2) 0.091(9) Uiso 1 1 d . . .
C6 C 0.69223(6) 0.5274(3) 0.44975(14) 0.0401(4) Uani 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0402(2) 0.0482(3) 0.0448(3) 0.00196(18) 0.01323(18) 0.00579(17)
N1 0.0409(8) 0.0624(10) 0.0408(8) 0.0028(7) 0.0186(6) 0.0013(7)
N2 0.0436(8) 0.0399(7) 0.0408(7) 0.0044(6) 0.0183(6) 0.0056(6)
N3 0.0442(8) 0.0460(9) 0.0454(8) 0.0021(7) 0.0173(7) 0.0068(6)
N4 0.0586(10) 0.0571(10) 0.0452(9) 0.0060(7) 0.0194(8) 0.0061(8)
N5 0.0529(9) 0.0607(10) 0.0505(9) 0.0028(8) 0.0236(8) 0.0040(8)
N6 0.0472(9) 0.0594(10) 0.0506(9) 0.0034(8) 0.0231(7) 0.0105(7)
C1 0.0466(12) 0.137(3) 0.0825(18) -0.0057(17) 0.0334(12) -0.0042(14)
C2 0.0482(10) 0.0465(10) 0.0390(9) -0.0016(8) 0.0132(8) -0.0061(8)
C3 0.0448(10) 0.0482(10) 0.0392(9) -0.0004(7) 0.0105(7) -0.0017(8)
C4 0.0547(11) 0.0533(11) 0.0369(9) -0.0057(8) 0.0167(8) 0.0026(8)
C5 0.0651(13) 0.0474(11) 0.0638(13) 0.0101(10) 0.0373(11) 0.0198(10)
C6 0.0420(9) 0.0403(9) 0.0411(9) -0.0033(7) 0.0158(7) 0.0073(7)
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C4 109.17(15) . . ?
C2 N1 C1 126.0(2) . . ?
C4 N1 C1 124.79(19) . . ?
C2 N2 C3 108.82(15) . . ?
C2 N2 C5 125.03(18) . . ?
C3 N2 C5 126.11(17) . . ?
C6 N3 N4 108.37(15) . . ?
N5 N4 N3 106.54(16) . . ?
N4 N5 N6 110.66(15) . . ?
C6 N6 N5 105.47(15) . . ?
N1 C2 N2 108.02(17) . . ?
C4 C3 N2 106.61(17) . . ?
C3 C4 N1 107.37(17) . . ?
N2 C5 C6 111.86(16) . . ?
N6 C6 N3 108.96(16) . . ?
N6 C6 C5 125.37(17) . . ?
N3 C6 C5 125.67(16) . . ?
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 C2 1.317(2) . ?
N1 C4 1.369(3) . ?
N1 C1 1.466(3) . ?
N2 C2 1.328(2) . ?
N2 C3 1.378(2) . ?
N2 C5 1.461(2) . ?
N3 C6 1.329(2) . ?
N3 N4 1.344(2) . ?
N4 N5 1.291(2) . ?
N5 N6 1.360(2) . ?
N6 C6 1.316(2) . ?
C3 C4 1.338(3) . ?
C5 C6 1.488(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653215
