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#$Date: 2016-03-23 01:36:30 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179148 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/09/4310918.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_4310918
loop_
_publ_author_name
'Philipp Kölle'
'Richard Dronskowski'
_publ_section_title
;
 Hydrogen Bonding in the Crystal Structures of the Ionic Liquid Compounds
 Butyldimethylimidazolium Hydrogen Sulfate, Chloride, and
 Chloroferrate(II,III)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2803
_journal_page_last               2809
_journal_paper_doi               10.1021/ic035237l
_journal_volume                  43
_journal_year                    2004
_chemical_formula_sum            'C9 H17 Cl N2'
_chemical_formula_weight         188.70
_chemical_melting_point          373(1)
_chemical_name_systematic        '1-butyl-2,3-dimethylimidazolium chloride'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.74(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3800(17)
_cell_length_b                   11.710(2)
_cell_length_c                   10.760(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1055.8(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0609
_diffrn_reflns_av_sigmaI/netI    0.0798
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7441
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.315
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1200
_refine_ls_R_factor_gt           0.0641
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0661P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1570
_reflns_number_gt                1497
_reflns_number_total             2614
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic035237lsi20031027_082338.cif
_cod_data_source_block           bdmimcl_213
_cod_original_cell_volume        1055.8(4)
_cod_database_code               4310918
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Cl Cl 0.06237(9) 0.21112(7) 0.77204(7) 0.0515(3) Uani 1 1 d . . .
C5 C -0.3602(3) -0.0696(2) 0.8863(3) 0.0397(7) Uani 1 1 d . . .
H5 H -0.3988 -0.1337 0.8447 0.060 Uiso 1 1 calc R . .
C2 C -0.3135(3) 0.1106(2) 0.9362(2) 0.0346(6) Uani 1 1 d . . .
N1 N -0.3898(3) 0.0431(2) 0.8550(2) 0.0368(6) Uani 1 1 d . . .
N3 N -0.2373(2) 0.04361(19) 1.01797(19) 0.0338(5) Uani 1 1 d . . .
C4 C -0.2655(3) -0.0692(2) 0.9877(3) 0.0377(6) Uani 1 1 d . . .
H4 H -0.2263 -0.1329 1.0297 0.045 Uiso 1 1 calc R . .
C6 C -0.1400(3) 0.0844(3) 1.1233(3) 0.0455(8) Uani 1 1 d . . .
H6A H -0.0976 0.0202 1.1683 0.055 Uiso 1 1 calc R . .
H6B H -0.2050 0.1294 1.1774 0.055 Uiso 1 1 calc R . .
H6C H -0.0538 0.1302 1.0931 0.055 Uiso 1 1 calc R . .
C7 C -0.3116(4) 0.2375(2) 0.9377(3) 0.0492(8) Uani 1 1 d . . .
H7A H -0.2472 0.2637 1.0064 0.059 Uiso 0.50 1 calc PR . .
H7B H -0.4186 0.2655 0.9462 0.059 Uiso 0.50 1 calc PR . .
H7C H -0.2679 0.2652 0.8614 0.059 Uiso 0.50 1 calc PR . .
H7D H -0.3752 0.2660 0.8696 0.059 Uiso 0.50 1 calc PR . .
H7E H -0.2039 0.2641 0.9298 0.059 Uiso 0.50 1 calc PR . .
H7F H -0.3546 0.2644 1.0146 0.059 Uiso 0.50 1 calc PR . .
C10 C -0.2849(4) 0.0323(3) 0.5818(3) 0.0445(7) Uani 1 1 d . . .
H10A H -0.2124 0.0005 0.6436 0.053 Uiso 1 1 calc R . .
H10B H -0.3541 -0.0287 0.5525 0.053 Uiso 1 1 calc R . .
C9 C -0.3854(3) 0.1242(3) 0.6415(2) 0.0425(7) Uani 1 1 d . . .
H9A H -0.4551 0.1575 0.5786 0.051 Uiso 1 1 calc R . .
H9B H -0.3155 0.1841 0.6724 0.051 Uiso 1 1 calc R . .
C8 C -0.4869(4) 0.0812(3) 0.7483(3) 0.0489(8) Uani 1 1 d . . .
H8A H -0.5575 0.1419 0.7747 0.059 Uiso 1 1 calc R . .
H8B H -0.5525 0.0182 0.7191 0.059 Uiso 1 1 calc R . .
C11 C -0.1901(4) 0.0775(3) 0.4745(3) 0.0636(10) Uani 1 1 d . . .
H11A H -0.1285 0.0168 0.4393 0.076 Uiso 1 1 calc R . .
H11B H -0.1198 0.1368 0.5035 0.076 Uiso 1 1 calc R . .
H11C H -0.2616 0.1079 0.4124 0.076 Uiso 1 1 calc R . .
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'
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'
H H 0.0000 0.0000 '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
H5 Cl H4 152.5 2_456 3_557 ?
H5 Cl C4 160.2 2_456 3_557 ?
H4 Cl C4 8.4 3_557 3_557 ?
H5 Cl C5 3.2 2_456 2_456 ?
H4 Cl C5 151.1 3_557 2_456 ?
C4 Cl C5 159.20(7) 3_557 2_456 ?
C4 C5 N1 107.3(2) . . ?
N3 C2 N1 107.7(2) . . ?
N3 C2 C7 125.1(2) . . ?
N1 C2 C7 127.2(3) . . ?
C2 N1 C5 108.8(2) . . ?
C2 N1 C8 126.0(3) . . ?
C5 N1 C8 125.2(2) . . ?
C2 N3 C4 109.2(2) . . ?
C2 N3 C6 125.0(2) . . ?
C4 N3 C6 125.8(2) . . ?
C5 C4 N3 107.0(2) . . ?
C11 C10 C9 112.1(3) . . ?
C10 C9 C8 113.8(2) . . ?
N1 C8 C9 112.4(2) . . ?
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
Cl H5 2.5909 2_456 ?
Cl H4 2.6830 3_557 ?
Cl C4 3.497(3) 3_557 ?
Cl C5 3.506(3) 2_456 ?
C5 C4 1.341(4) . ?
C5 N1 1.384(4) . ?
C2 N3 1.335(3) . ?
C2 N1 1.335(3) . ?
C2 C7 1.486(4) . ?
N1 C8 1.469(4) . ?
N3 C4 1.381(3) . ?
N3 C6 1.467(3) . ?
C10 C11 1.506(4) . ?
C10 C9 1.515(4) . ?
C9 C8 1.523(4) . ?
