#------------------------------------------------------------------------------
#$Date: 2022-09-21 10:27:06 +0300 (Wed, 21 Sep 2022) $
#$Revision: 278022 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/58/8105808.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_8105808
loop_
_publ_author_name
'Li, Zongmu'
_publ_section_title
;
 The crystal structure of
 dichlorido-bis(1-butyl-1H-imidazole-\kN)zinc(II), C14H24Cl2ZnN4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              649
_journal_page_last               651
_journal_paper_doi               10.1515/ncrs-2019-0001
_journal_volume                  234
_journal_year                    2019
_chemical_formula_sum            'C14 H24 Cl2 N4 Zn'
_chemical_formula_weight         384.64
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.3238(11)
_cell_length_b                   15.9366(13)
_cell_length_c                   18.0943(16)
_cell_measurement_reflns_used    4.51
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.556
_cell_measurement_theta_min      2.556
_cell_volume                     3842.1(6)
_computing_cell_refinement       'SMART [1]'
_computing_data_collection       'SMART [1]'
_computing_data_reduction        'SMART [1]'
_computing_molecular_graphics    'XP in SHELXTL [2]'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)[2]'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2015)[2]'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17488
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.015
_diffrn_reflns_theta_max         25.015
_diffrn_reflns_theta_min         2.556
_exptl_absorpt_coefficient_mu    1.555
_exptl_absorpt_correction_T_max  0.7671
_exptl_absorpt_correction_T_min  0.7359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       0.0030(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0372P)²+3.5287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.1053
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2163
_reflns_number_total             3387
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0001_suppl.cif
_cod_data_source_block           lzm
_cod_database_code               8105808
_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   0.736
_shelx_estimated_absorpt_t_max   0.767
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.27259(3) 0.01046(3) 0.54028(2) 0.04888(18) Uani 1 1 d . . . . .
Cl1 Cl 0.12184(8) 0.00207(7) 0.59470(7) 0.0712(3) Uani 1 1 d . . . . .
Cl2 Cl 0.39173(8) -0.07427(7) 0.58430(6) 0.0694(3) Uani 1 1 d . . . . .
N1 N 0.3192(2) 0.13022(19) 0.54875(17) 0.0528(8) Uani 1 1 d . . . . .
N2 N 0.4098(3) 0.2424(2) 0.5307(2) 0.0672(10) Uani 1 1 d . . . . .
N3 N 0.2525(2) -0.00860(19) 0.43056(18) 0.0509(8) Uani 1 1 d . . . . .
N4 N 0.1766(3) -0.0171(2) 0.32355(17) 0.0599(9) Uani 1 1 d . . . . .
C1 C 0.4012(3) 0.1601(3) 0.5192(2) 0.0618(11) Uani 1 1 d . . . . .
H1 H 0.447705 0.127911 0.493442 0.074 Uiso 1 1 calc R U . . .
C2 C 0.2720(3) 0.1975(3) 0.5803(2) 0.0657(12) Uani 1 1 d . . . . .
H2 H 0.210971 0.195981 0.605144 0.079 Uiso 1 1 calc R U . . .
C3 C 0.3284(4) 0.2663(3) 0.5695(3) 0.0736(14) Uani 1 1 d . . . . .
H3 H 0.314003 0.320299 0.585685 0.088 Uiso 1 1 calc R U . . .
C4 C 0.4937(4) 0.2950(3) 0.5055(3) 0.0982(19) Uani 1 1 d . . . . .
H4A H 0.467129 0.347662 0.487012 0.118 Uiso 1 1 calc R U . . .
H4B H 0.527288 0.267020 0.464858 0.118 Uiso 1 1 calc R U . . .
C5 C 0.5684(4) 0.3131(3) 0.5645(3) 0.0772(14) Uani 1 1 d . . . . .
H5A H 0.618203 0.351553 0.544920 0.093 Uiso 1 1 calc R U . . .
H5B H 0.534487 0.341231 0.604919 0.093 Uiso 1 1 calc R U . . .
C6 C 0.6205(4) 0.2383(3) 0.5939(4) 0.0990(18) Uani 1 1 d . . . . .
H6A H 0.649307 0.206765 0.553243 0.119 Uiso 1 1 calc R U . . .
H6B H 0.572228 0.202425 0.618657 0.119 Uiso 1 1 calc R U . . .
C7 C 0.7022(5) 0.2614(5) 0.6473(5) 0.168(4) Uani 1 1 d . . . . .
H7A H 0.752512 0.293663 0.622120 0.252 Uiso 1 1 calc R U . . .
H7B H 0.731881 0.211270 0.666948 0.252 Uiso 1 1 calc R U . . .
H7C H 0.674330 0.294035 0.686865 0.252 Uiso 1 1 calc R U . . .
C8 C 0.1661(3) -0.0149(2) 0.3967(2) 0.0512(10) Uani 1 1 d . . . . .
H8 H 0.104569 -0.017579 0.420893 0.061 Uiso 1 1 calc R U . . .
C9 C 0.3228(4) -0.0060(3) 0.3765(3) 0.0675(12) Uani 1 1 d . . . . .
H9 H 0.391622 -0.001345 0.384100 0.081 Uiso 1 1 calc R U . . .
C10 C 0.2779(4) -0.0112(3) 0.3105(3) 0.0734(13) Uani 1 1 d . . . . .
H10 H 0.309270 -0.010906 0.264545 0.088 Uiso 1 1 calc R U . . .
C11 C 0.0964(4) -0.0262(3) 0.2685(2) 0.0813(15) Uani 1 1 d . . . . .
H11A H 0.110616 0.009783 0.226562 0.098 Uiso 1 1 calc R U . . .
H11B H 0.033257 -0.008150 0.289981 0.098 Uiso 1 1 calc R U . . .
C12 C 0.0863(4) -0.1158(4) 0.2422(3) 0.0943(17) Uani 1 1 d . . . . .
H12A H 0.042092 -0.116885 0.199557 0.113 Uiso 1 1 calc R U . . .
H12B H 0.151619 -0.135624 0.226238 0.113 Uiso 1 1 calc R U . . .
C13 C 0.0462(4) -0.1748(4) 0.2992(3) 0.1025(18) Uani 1 1 d . . . . .
H13A H -0.020701 -0.156635 0.313032 0.123 Uiso 1 1 calc R U . . .
H13B H 0.088154 -0.171095 0.342891 0.123 Uiso 1 1 calc R U . . .
C14 C 0.0410(6) -0.2657(4) 0.2754(4) 0.151(3) Uani 1 1 d . . . . .
H14A H -0.009331 -0.271921 0.237793 0.227 Uiso 1 1 calc R U . . .
H14B H 0.024026 -0.300088 0.317087 0.227 Uiso 1 1 calc R U . . .
H14C H 0.104952 -0.282686 0.256092 0.227 Uiso 1 1 calc R U . . .
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'
Zn Zn 0.2839 1.4301 '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
N1 Zn1 N3 104.92(13) . .
N1 Zn1 Cl2 109.11(9) . .
N3 Zn1 Cl2 110.68(9) . .
N1 Zn1 Cl1 107.43(10) . .
N3 Zn1 Cl1 107.63(10) . .
Cl2 Zn1 Cl1 116.41(5) . .
C1 N1 C2 105.6(4) . .
C1 N1 Zn1 124.9(3) . .
C2 N1 Zn1 129.3(3) . .
C1 N2 C3 106.9(4) . .
C1 N2 C4 125.4(4) . .
C3 N2 C4 127.7(4) . .
C8 N3 C9 105.8(3) . .
C8 N3 Zn1 125.9(3) . .
C9 N3 Zn1 127.7(3) . .
C8 N4 C10 105.8(3) . .
C8 N4 C11 126.9(4) . .
C10 N4 C11 127.2(4) . .
N1 C1 N2 111.5(4) . .
C3 C2 N1 108.8(4) . .
C2 C3 N2 107.2(4) . .
N2 C4 C5 113.4(4) . .
C6 C5 C4 114.6(4) . .
C5 C6 C7 112.0(5) . .
N3 C8 N4 112.0(4) . .
C10 C9 N3 109.5(4) . .
C9 C10 N4 106.8(4) . .
N4 C11 C12 111.9(4) . .
C13 C12 C11 114.1(4) . .
C12 C13 C14 114.9(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N1 2.013(3) .
Zn1 N3 2.026(3) .
Zn1 Cl2 2.2311(11) .
Zn1 Cl1 2.2409(12) .
N1 C1 1.306(5) .
N1 C2 1.368(5) .
N2 C1 1.333(5) .
N2 C3 1.346(6) .
N2 C4 1.470(6) .
N3 C8 1.308(5) .
N3 C9 1.355(5) .
N4 C8 1.332(5) .
N4 C10 1.374(5) .
N4 C11 1.468(5) .
C2 C3 1.343(6) .
C4 C5 1.487(6) .
C5 C6 1.480(7) .
C6 C7 1.500(8) .
C9 C10 1.339(6) .
C11 C12 1.512(6) .
C12 C13 1.495(7) .
C13 C14 1.512(8) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 Cl2 0.93 2.70 3.605(5) 164.7 5_656 yes
C11 H11A Cl2 0.97 2.77 3.701(5) 160.7 2_554 yes
C11 H11B Cl1 0.97 2.94 3.838(5) 154.7 5_556 yes
C1 H1 Cl2 0.93 2.70 3.605(5) 164.7 5_656 yes
C11 H11A Cl2 0.97 2.77 3.701(5) 160.7 2_554 yes
C11 H11B Cl1 0.97 2.94 3.838(5) 154.7 5_556 yes
