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#$Date: 2020-01-04 23:54:05 +0200 (Sat, 04 Jan 2020) $
#$Revision: 246593 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/57/7125750.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_7125750
loop_
_publ_author_name
'Kureja, Kunal'
'Zinke, Julian'
'Bruhn, Clemens'
'Siemeling, Ulrich'
_publ_section_title
;
 Imidazolium-benzimidazolates as convenient sources of
 donor-functionalised normal and abnormal N-heterocyclic carbenes.
;
_journal_issue                   65
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9705
_journal_page_last               9708
_journal_paper_doi               10.1039/c9cc05283f
_journal_volume                  55
_journal_year                    2019
_chemical_formula_moiety         'C14 H17 N4, Cl'
_chemical_formula_sum            'C14 H17 Cl N4'
_chemical_formula_weight         276.76
_space_group_crystal_system      orthorhombic
_space_group_IT_number           64
_space_group_name_Hall           '-C 2ac 2'
_space_group_name_H-M_alt        'C m c e'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-07-08 deposited with the CCDC.	2019-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.4586(5)
_cell_length_b                   24.9625(12)
_cell_length_c                   17.2461(7)
_cell_measurement_reflns_used    4848
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      1.63
_cell_volume                     2780.5(3)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 Pilatus200K
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      ' 356 frames, detector distance = 60 mm'
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            6154
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_min         1.632
_diffrn_source                   'Mo Genix'
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.267
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       plate
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0918
_refine_ls_R_factor_gt           0.0512
_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)+(0.0506P)²+4.1580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1231
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1038
_reflns_number_total             1493
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc05283f2.cif
_cod_data_source_block           sv0621
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_original_sg_symbol_H-M      'C m c a'
_cod_database_code               7125750
_shelx_shelxl_version_number     2017/1
_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   0.939
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x, -y, -z'
'-x, y+1/2, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1, -z+1/2'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x, y, z'
'x, -y-1/2, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'-x+1/2, y+1/2, z'
'x+1/2, -y, 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.500000 0.20969(13) 0.6289(2) 0.0205(9) Uani 1 2 d S T P
H1A H 0.500000 0.205440 0.683691 0.025 Uiso 1 2 calc R U P
C2 C 0.500000 0.19338(14) 0.5044(2) 0.0231(9) Uani 1 2 d S T P
H2A H 0.500000 0.174513 0.456565 0.028 Uiso 1 2 calc R U P
C3 C 0.500000 0.24664(15) 0.51238(19) 0.0203(8) Uani 1 2 d S T P
H3A H 0.500000 0.272578 0.472073 0.024 Uiso 1 2 calc R U P
C4 C 0.500000 0.30726(14) 0.6248(2) 0.0197(8) Uani 1 2 d S T P
C5 C 0.500000 0.36878(16) 0.7132(2) 0.0399(12) Uani 1 2 d S T P
C6 C 0.500000 0.39973(17) 0.7798(2) 0.0631(18) Uani 1 2 d S T P
H6A H 0.500000 0.383926 0.829905 0.076 Uiso 1 2 calc R U P
C7 C 0.500000 0.45432(18) 0.7701(3) 0.081(2) Uani 1 2 d S T P
H7A H 0.500000 0.476806 0.814561 0.097 Uiso 1 2 calc R U P
C8 C 0.500000 0.47773(18) 0.6959(3) 0.074(2) Uani 1 2 d S T P
H8A H 0.500000 0.515657 0.691387 0.089 Uiso 1 2 calc R U P
C9 C 0.500000 0.44700(16) 0.6301(2) 0.0507(15) Uani 1 2 d S T P
H9A H 0.500000 0.463027 0.580155 0.061 Uiso 1 2 calc R U P
C10 C 0.500000 0.39153(15) 0.6388(2) 0.0360(12) Uani 1 2 d S T P
C11 C 0.500000 0.11181(14) 0.5956(2) 0.0202(8) Uani 1 2 d S T P
C12 C 0.5884(9) 0.10413(19) 0.6758(3) 0.0291(14) Uani 0.5 1 d . . P
H12A H 0.727733 0.119620 0.678083 0.044 Uiso 0.5 1 calc R U P
H12B H 0.595706 0.065777 0.687692 0.044 Uiso 0.5 1 calc R U P
H12C H 0.499286 0.121999 0.713855 0.044 Uiso 0.5 1 calc R U P
C13 C 0.6258(11) 0.0823(2) 0.5356(4) 0.0435(17) Uani 0.5 1 d . . P
H13A H 0.561432 0.086618 0.484534 0.065 Uiso 0.5 1 calc R U P
H13B H 0.631153 0.044123 0.548920 0.065 Uiso 0.5 1 calc R U P
H13C H 0.766663 0.096847 0.534377 0.065 Uiso 0.5 1 calc R U P
C14 C 0.2696(9) 0.0941(2) 0.5935(3) 0.0302(14) Uani 0.5 1 d . . P
H14A H 0.191843 0.113732 0.633225 0.045 Uiso 0.5 1 calc R U P
H14B H 0.260274 0.055598 0.603670 0.045 Uiso 0.5 1 calc R U P
H14C H 0.211114 0.101967 0.542293 0.045 Uiso 0.5 1 calc R U P
Cl1 Cl 0.500000 0.22338(4) 0.82542(5) 0.0270(3) Uani 1 2 d S T P
N1 N 0.500000 0.17020(11) 0.57753(15) 0.0175(7) Uani 1 2 d S T P
N2 N 0.500000 0.25622(11) 0.59136(15) 0.0163(7) Uani 1 2 d S T P
N3 N 0.500000 0.31400(12) 0.70230(16) 0.0282(8) Uani 1 2 d S T P
H3 H 0.500000 0.288933 0.738173 0.034 Uiso 1 2 calc R U P
N4 N 0.500000 0.35111(12) 0.58311(16) 0.0240(8) Uani 1 2 d S T P
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'
Cl Cl 0.1484 0.1585 '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'
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 C1 N2 108.9(3) . .
N1 C1 H1A 125.6 . .
N2 C1 H1A 125.6 . .
C3 C2 N1 108.7(3) . .
C3 C2 H2A 125.6 . .
N1 C2 H2A 125.6 . .
C2 C3 N2 105.9(3) . .
C2 C3 H3A 127.1 . .
N2 C3 H3A 127.1 . .
N4 C4 N3 116.1(3) . .
N4 C4 N2 122.4(3) . .
N3 C4 N2 121.5(3) . .
N3 C5 C6 131.7(4) . .
N3 C5 C10 106.1(3) . .
C6 C5 C10 122.2(4) . .
C7 C6 C5 116.9(4) . .
C7 C6 H6A 121.5 . .
C5 C6 H6A 121.5 . .
C6 C7 C8 121.5(4) . .
C6 C7 H7A 119.2 . .
C8 C7 H7A 119.2 . .
C9 C8 C7 121.4(4) . .
C9 C8 H8A 119.3 . .
C7 C8 H8A 119.3 . .
C8 C9 C10 117.9(4) . .
C8 C9 H9A 121.1 . .
C10 C9 H9A 121.1 . .
N4 C10 C9 130.3(3) . .
N4 C10 C5 109.7(3) . .
C9 C10 C5 120.0(4) . .
N1 C11 C13 109.6(3) . 11_655
N1 C11 C13 109.6(3) . .
C13 C11 C13 65.2(6) 11_655 .
N1 C11 C12 108.4(3) . .
C13 C11 C12 140.4(4) 11_655 .
C13 C11 C12 111.3(4) . .
N1 C11 C12 108.4(3) . 11_655
C13 C11 C12 111.3(4) 11_655 11_655
C13 C11 C12 140.4(4) . 11_655
C12 C11 C12 44.5(5) . 11_655
N1 C11 C14 105.8(2) . .
C13 C11 C14 47.8(3) 11_655 .
C13 C11 C14 111.2(4) . .
C12 C11 C14 110.3(4) . .
C12 C11 C14 67.8(3) 11_655 .
N1 C11 C14 105.8(2) . 11_655
C13 C11 C14 111.2(4) 11_655 11_655
C13 C11 C14 47.8(3) . 11_655
C12 C11 C14 67.8(3) . 11_655
C12 C11 C14 110.3(4) 11_655 11_655
C14 C11 C14 146.9(5) . 11_655
C11 C12 H12A 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C11 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C11 C13 H13A 109.5 . .
C11 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C11 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C11 C14 H14A 109.5 . .
C11 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C11 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C1 N1 C2 107.3(3) . .
C1 N1 C11 126.0(3) . .
C2 N1 C11 126.7(3) . .
C1 N2 C3 109.2(3) . .
C1 N2 C4 126.5(3) . .
C3 N2 C4 124.3(3) . .
C4 N3 C5 105.0(3) . .
C4 N3 H3 127.5 . .
C5 N3 H3 127.5 . .
C4 N4 C10 103.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.326(4) .
C1 N2 1.330(4) .
C1 H1A 0.9500 .
C2 C3 1.337(5) .
C2 N1 1.388(4) .
C2 H2A 0.9500 .
C3 N2 1.383(4) .
C3 H3A 0.9500 .
C4 N4 1.309(4) .
C4 N3 1.348(4) .
C4 N2 1.398(4) .
C5 N3 1.380(5) .
C5 C6 1.385(5) .
C5 C10 1.403(5) .
C6 C7 1.373(6) .
C6 H6A 0.9500 .
C7 C8 1.406(6) .
C7 H7A 0.9500 .
C8 C9 1.370(6) .
C8 H8A 0.9500 .
C9 C10 1.393(5) .
C9 H9A 0.9500 .
C10 N4 1.393(5) .
C11 N1 1.490(4) .
C11 C13 1.508(6) 11_655
C11 C13 1.508(6) .
C11 C12 1.510(6) .
C11 C12 1.510(6) 11_655
C11 C14 1.553(6) .
C11 C14 1.553(6) 11_655
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
N3 H3 0.8800 .
