#------------------------------------------------------------------------------
#$Date: 2016-05-06 04:17:31 +0300 (Fri, 06 May 2016) $
#$Revision: 182688 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/05/2020501.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_2020501
loop_
_publ_author_name
'Cebollada, Andrea'
'Vellé, Alba'
'Sanz Miguel, Pablo J.'
_publ_section_title
;
 Hirshfeld and DFT analysis of the N-heterocyclic carbene proligand
 methylenebis(N-butylimidazolium) as the acetonitrile-solvated diiodide
 salt
;
_journal_coeditor_code           EG3202
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section C Structural Chemistry'
_journal_paper_doi               10.1107/S2053229616006781
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C15 H26 N4 2+, 2I -, C2 H3 N'
_chemical_formula_moiety         'C15 H26 N4 2+, 2(I -), C2 H3 N'
_chemical_formula_sum            'C17 H29 I2 N5'
_chemical_formula_weight         557.25
_chemical_name_systematic
;
1,1'-Methylenebis(3-butylimidazolium) diiodide acetonitrile monosolvate
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                101.7655(5)
_cell_angle_beta                 93.2300(5)
_cell_angle_gamma                99.0746(5)
_cell_formula_units_Z            2
_cell_length_a                   5.2513(2)
_cell_length_b                   13.9534(6)
_cell_length_c                   16.0336(7)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.51
_cell_measurement_theta_min      2.20
_cell_volume                     1130.99(8)
_computing_cell_refinement
;
SAINT (Bruker, 2011)
;
_computing_data_collection
;
APEX2 (Bruker, 2011)
;
_computing_data_reduction
;
SAINT (Bruker, 2011)
;
_computing_molecular_graphics
;
SHELXTL (Bruker, 2011)
;
_computing_publication_material
;
SHELXTL (Bruker, 2011)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14589
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.603
_diffrn_reflns_theta_min         1.514
_exptl_absorpt_coefficient_mu    2.789
_exptl_absorpt_correction_T_max  0.658
_exptl_absorpt_correction_T_min  0.441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2011)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       prisms
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.420
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0188
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0224P)²+0.5576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0455
_refine_ls_wR_factor_ref         0.0468
_reflns_number_gt                4794
_reflns_number_total             5242
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            eg3202sup1.cif
_cod_data_source_block           I
_cod_database_code               2020501
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.367
_shelx_estimated_absorpt_t_max   0.680
loop_
_space_group_symop_operation_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_occupancy
I I1 0.42021(2) 0.58093(2) 0.35311(2) 0.01844(4) Uani d 1
I I2 0.72032(2) 0.76194(2) 0.00980(2) 0.02117(4) Uani d 1
N N11 -0.1149(3) 0.36742(12) 0.23753(10) 0.0182(3) Uani d 1
C C12 -0.1418(4) 0.39156(14) 0.32081(12) 0.0182(4) Uani d 1
H H12 -0.2492 0.4357 0.3468 0.022 Uiso calc 1
N N13 0.0060(3) 0.34381(12) 0.36144(10) 0.0162(3) Uani d 1
C C14 0.1377(4) 0.28869(15) 0.30215(13) 0.0195(4) Uani d 1
H H14 0.2585 0.2481 0.3140 0.023 Uiso calc 1
C C15 0.0630(4) 0.30320(15) 0.22457(13) 0.0204(4) Uani d 1
H H15 0.1206 0.2750 0.1714 0.024 Uiso calc 1
C C16 0.0363(4) 0.35405(15) 0.45488(12) 0.0192(4) Uani d 1
H H161 -0.0679 0.4031 0.4820 0.023 Uiso calc 1
H H162 0.2201 0.3797 0.4760 0.023 Uiso calc 1
C C17 -0.0480(4) 0.25647(15) 0.48106(13) 0.0201(4) Uani d 1
H H171 -0.0251 0.2677 0.5442 0.024 Uiso calc 1
H H172 0.0656 0.2092 0.4576 0.024 Uiso calc 1
C C18 -0.3285(4) 0.20997(15) 0.45049(13) 0.0216(4) Uani d 1
H H181 -0.4391 0.2614 0.4634 0.026 Uiso calc 1
H H182 -0.3441 0.1853 0.3877 0.026 Uiso calc 1
C C19 -0.4247(5) 0.12446(17) 0.49273(16) 0.0313(5) Uani d 1
H H191 -0.5990 0.0923 0.4671 0.047 Uiso calc 1
H H192 -0.4298 0.1501 0.5541 0.047 Uiso calc 1
H H193 -0.3073 0.0760 0.4841 0.047 Uiso calc 1
N N21 -0.0729(3) 0.49440(12) 0.15562(10) 0.0196(3) Uani d 1
C C22 -0.0651(4) 0.58842(15) 0.19695(13) 0.0190(4) Uani d 1
H H22 -0.1740 0.6105 0.2396 0.023 Uiso calc 1
N N23 0.1212(3) 0.64552(13) 0.16814(11) 0.0188(3) Uani d 1
C C24 0.2411(4) 0.58611(16) 0.10818(13) 0.0237(4) Uani d 1
H H24 0.3823 0.6079 0.0782 0.028 Uiso calc 1
C C25 0.1201(4) 0.49146(16) 0.10025(13) 0.0232(4) Uani d 1
H H25 0.1596 0.4340 0.0638 0.028 Uiso calc 1
C C26 0.2100(4) 0.75326(15) 0.19954(14) 0.0225(4) Uani d 1
H H261 0.2452 0.7841 0.1500 0.027 Uiso calc 1
H H262 0.3748 0.7640 0.2361 0.027 Uiso calc 1
C C27 0.0177(4) 0.80450(15) 0.25005(13) 0.0219(4) Uani d 1
H H271 -0.0055 0.7790 0.3029 0.026 Uiso calc 1
H H272 -0.1520 0.7899 0.2157 0.026 Uiso calc 1
C C28 0.1121(4) 0.91589(16) 0.27323(16) 0.0290(5) Uani d 1
H H281 0.1403 0.9404 0.2201 0.035 Uiso calc 1
H H282 0.2807 0.9298 0.3081 0.035 Uiso calc 1
C C29 -0.0770(5) 0.9724(2) 0.3228(2) 0.0431(6) Uani d 1
H H291 -0.0081 1.0438 0.3352 0.065 Uiso calc 1
H H292 -0.1005 0.9504 0.3765 0.065 Uiso calc 1
H H293 -0.2441 0.9593 0.2884 0.065 Uiso calc 1
C C31 -0.2422(4) 0.40854(15) 0.17320(13) 0.0232(4) Uani d 1
H H311 -0.4040 0.4288 0.1937 0.028 Uiso calc 1
H H312 -0.2884 0.3570 0.1198 0.028 Uiso calc 1
N N41 0.4743(4) 0.13329(17) 0.21320(14) 0.0380(5) Uani d 1
C C42 0.5987(4) 0.10146(17) 0.16261(15) 0.0286(5) Uani d 1
C C43 0.7612(5) 0.06174(19) 0.09817(19) 0.0414(6) Uani d 1
H H431 0.7504 0.0945 0.0498 0.062 Uiso calc 1
H H432 0.7016 -0.0099 0.0782 0.062 Uiso calc 1
H H433 0.9412 0.0740 0.1231 0.062 Uiso calc 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'
I I -0.4742 1.8119 '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_publ_flag
C12 N11 C15 108.78(16) y
N13 C12 N11 108.64(17) y
N13 C12 H12 125.7 ?
N11 C12 H12 125.7 ?
C12 N13 C14 108.63(16) y
C15 C14 N13 107.39(18) y
C15 C14 H14 126.3 ?
N13 C14 H14 126.3 ?
C14 C15 N11 106.54(17) y
C12 N11 C31 124.01(18) y
C15 N11 C31 127.10(17) y
C12 N13 C16 124.92(16) y
C14 N13 C16 126.33(17) y
C14 C15 H15 126.7 ?
N11 C15 H15 126.7 ?
N13 C16 C17 112.29(16) y
N13 C16 H161 109.1 ?
C17 C16 H161 109.1 ?
N13 C16 H162 109.1 ?
C17 C16 H162 109.1 ?
H161 C16 H162 107.9 ?
C16 C17 C18 113.26(17) y
C16 C17 H171 108.9 ?
C18 C17 H171 108.9 ?
C16 C17 H172 108.9 ?
C18 C17 H172 108.9 ?
H171 C17 H172 107.7 ?
C19 C18 C17 112.06(18) y
N11 C31 N21 110.80(16) y
C19 C18 H181 109.2 ?
C17 C18 H181 109.2 ?
C19 C18 H182 109.2 ?
C17 C18 H182 109.2 ?
H181 C18 H182 107.9 ?
C18 C19 H191 109.5 ?
C18 C19 H192 109.5 ?
H191 C19 H192 109.5 ?
C18 C19 H193 109.5 ?
H191 C19 H193 109.5 ?
H192 C19 H193 109.5 ?
C22 N21 C25 109.01(17) y
C22 N21 C31 124.65(18) ?
N23 C22 N21 108.14(18) y
N23 C22 H22 125.9 ?
N21 C22 H22 125.9 ?
C22 N23 C24 108.93(17) y
C25 C24 N23 107.27(18) y
C25 C24 H24 126.4 ?
N23 C24 H24 126.4 ?
C24 C25 N21 106.63(19) y
C25 N21 C31 126.08(18) y
C22 N23 C26 126.91(17) y
C24 N23 C26 123.88(17) y
C24 C25 H25 126.7 ?
N21 C25 H25 126.7 ?
N23 C26 C27 113.44(16) y
N23 C26 H261 108.9 ?
C27 C26 H261 108.9 ?
N23 C26 H262 108.9 ?
C27 C26 H262 108.9 ?
H261 C26 H262 107.7 ?
C26 C27 C28 110.24(17) y
C26 C27 H271 109.6 ?
C28 C27 H271 109.6 ?
C26 C27 H272 109.6 ?
C28 C27 H272 109.6 ?
H271 C27 H272 108.1 ?
C27 C28 C29 112.85(19) y
C27 C28 H281 109.0 ?
C29 C28 H281 109.0 ?
C27 C28 H282 109.0 ?
C29 C28 H282 109.0 ?
H281 C28 H282 107.8 ?
C28 C29 H291 109.5 ?
C28 C29 H292 109.5 ?
H291 C29 H292 109.5 ?
C28 C29 H293 109.5 ?
H291 C29 H293 109.5 ?
H292 C29 H293 109.5 ?
N11 C31 H311 109.5 ?
N21 C31 H311 109.5 ?
N11 C31 H312 109.5 ?
N21 C31 H312 109.5 ?
H311 C31 H312 108.1 ?
N41 C42 C43 179.2(3) ?
C42 C43 H431 109.5 ?
C42 C43 H432 109.5 ?
H431 C43 H432 109.5 ?
C42 C43 H433 109.5 ?
H431 C43 H433 109.5 ?
H432 C43 H433 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N11 C12 1.330(3) y
N11 C15 1.389(3) y
N11 C31 1.457(3) y
C12 N13 1.324(3) y
C12 H12 0.9500 ?
N13 C14 1.385(2) y
N13 C16 1.473(2) y
C14 C15 1.347(3) y
C14 H14 0.9500 ?
C15 H15 0.9500 ?
C16 C17 1.513(3) y
C16 H161 0.9900 ?
C16 H162 0.9900 ?
C17 C18 1.523(3) y
C17 H171 0.9900 ?
C17 H172 0.9900 ?
C18 C19 1.522(3) y
C18 H181 0.9900 ?
C18 H182 0.9900 ?
C19 H191 0.9800 ?
C19 H192 0.9800 ?
C19 H193 0.9800 ?
N21 C22 1.337(3) y
N21 C25 1.384(3) y
N21 C31 1.461(2) y
C22 N23 1.327(3) y
C22 H22 0.9500 ?
N23 C24 1.384(3) y
N23 C26 1.475(3) y
C24 C25 1.350(3) y
C24 H24 0.9500 ?
C25 H25 0.9500 ?
C26 C27 1.507(3) y
C26 H261 0.9900 ?
C26 H262 0.9900 ?
C27 C28 1.517(3) y
C27 H271 0.9900 ?
C27 H272 0.9900 ?
C28 C29 1.523(3) y
C28 H281 0.9900 ?
C28 H282 0.9900 ?
C29 H291 0.9800 ?
C29 H292 0.9800 ?
C29 H293 0.9800 ?
C31 H311 0.9900 ?
C31 H312 0.9900 ?
N41 C42 1.134(3) ?
C42 C43 1.456(3) ?
C43 H431 0.9800 ?
C43 H432 0.9800 ?
C43 H433 0.9800 ?
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
C15 N11 C12 N13 -1.5(2)
C31 N11 C12 N13 -177.84(16)
N11 C12 N13 C14 1.5(2)
N11 C12 N13 C16 177.62(17)
C12 N13 C14 C15 -0.9(2)
C16 N13 C14 C15 -176.96(17)
N13 C14 C15 N11 0.0(2)
C12 N11 C15 C14 0.9(2)
C31 N11 C15 C14 177.14(18)
C12 N13 C16 C17 119.9(2)
C14 N13 C16 C17 -64.6(2)
N13 C16 C17 C18 -58.1(2)
C16 C17 C18 C19 -168.04(18)
C25 N21 C22 N23 1.7(2)
C31 N21 C22 N23 176.07(17)
N21 C22 N23 C24 -1.6(2)
N21 C22 N23 C26 -175.68(18)
C22 N23 C24 C25 1.0(2)
C26 N23 C24 C25 175.23(18)
N23 C24 C25 N21 0.1(2)
C22 N21 C25 C24 -1.1(2)
C31 N21 C25 C24 -175.36(18)
C22 N23 C26 C27 -18.8(3)
C24 N23 C26 C27 168.00(18)
N23 C26 C27 C28 -174.97(18)
C26 C27 C28 C29 178.7(2)
C12 N11 C31 N21 94.2(2)
C15 N11 C31 N21 -81.5(2)
C22 N21 C31 N11 -90.3(2)
C25 N21 C31 N11 83.1(2)

_cod_database_fobs_code 2020501
