#------------------------------------------------------------------------------
#$Date: 2021-08-20 04:12:43 +0300 (Fri, 20 Aug 2021) $
#$Revision: 268148 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243397.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_7243397
loop_
_publ_author_name
'Asressu, Kesatebrhan Haile'
'Chan, Chieh-Kai'
'Wang, Cheng-Chung'
_publ_section_title
;
 TMSOTf-catalyzed synthesis of trisubstituted imidazoles using
 hexamethyldisilazane as a nitrogen source under neat and microwave
 irradiation conditions
;
_journal_issue                   45
_journal_name_full               'RSC Advances'
_journal_page_first              28061
_journal_page_last               28071
_journal_paper_doi               10.1039/D1RA05802A
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H18 N2'
_chemical_formula_sum            'C22 H18 N2'
_chemical_formula_weight         310.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-06 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.9490(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7445(3)
_cell_length_b                   19.4078(5)
_cell_length_c                   8.7809(2)
_cell_measurement_reflns_used    7607
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.31
_cell_volume                     1686.13(8)
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            24629
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.764
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9987
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       niddle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3652
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0334
_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)+(0.0351P)²+0.6802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0808
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.911
_reflns_Friedel_fraction_max     0.887
_reflns_number_gt                3331
_reflns_number_total             3652
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra05802a2.cif
_cod_data_source_block           i18082
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7243397
_shelx_shelxl_version_number     2018/3
_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   0.983
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_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'
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
N1 N 0.53057(17) 0.48640(9) 0.3924(2) 0.0171(4) Uani 1 1 d . . . . .
H1 H 0.521(3) 0.5163(14) 0.311(4) 0.030(7) Uiso 1 1 d . . . . .
N2 N 0.49254(18) 0.43381(8) 0.5938(2) 0.0172(3) Uani 1 1 d . . . . .
C1 C 0.45827(19) 0.48640(10) 0.4888(2) 0.0172(4) Uani 1 1 d . . . . .
C2 C 0.6145(2) 0.42955(10) 0.4339(2) 0.0180(4) Uani 1 1 d . . . . .
C3 C 0.5908(2) 0.39754(10) 0.5608(2) 0.0173(4) Uani 1 1 d . . . . .
C4 C 0.3619(2) 0.54176(11) 0.4802(2) 0.0195(4) Uani 1 1 d . . . . .
C5 C 0.2378(2) 0.52841(12) 0.4920(3) 0.0244(5) Uani 1 1 d . . . . .
C6 C 0.1545(3) 0.58469(13) 0.4837(3) 0.0342(6) Uani 1 1 d . . . . .
H6 H 0.069661 0.576997 0.490930 0.041 Uiso 1 1 calc R U . . .
C7 C 0.1920(3) 0.65125(14) 0.4652(4) 0.0389(6) Uani 1 1 d . . . . .
H7 H 0.133536 0.688563 0.461246 0.047 Uiso 1 1 calc R U . . .
C8 C 0.3140(3) 0.66369(12) 0.4526(3) 0.0332(6) Uani 1 1 d . . . . .
H8 H 0.339639 0.709429 0.439295 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3989(2) 0.60904(11) 0.4594(3) 0.0245(5) Uani 1 1 d . . . . .
H9 H 0.482720 0.617328 0.449952 0.029 Uiso 1 1 calc R U . . .
C10 C 0.1907(2) 0.45666(13) 0.5083(3) 0.0306(5) Uani 1 1 d . . . . .
H10A H 0.097769 0.458508 0.502215 0.046 Uiso 1 1 calc R U . . .
H10B H 0.249824 0.437033 0.614863 0.046 Uiso 1 1 calc R U . . .
H10C H 0.194050 0.427780 0.418406 0.046 Uiso 1 1 calc R U . . .
C11 C 0.6982(2) 0.41303(11) 0.3409(2) 0.0191(4) Uani 1 1 d . . . . .
C12 C 0.7640(2) 0.46496(12) 0.2914(3) 0.0233(5) Uani 1 1 d . . . . .
H12 H 0.758525 0.511322 0.322907 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8376(2) 0.44924(13) 0.1960(3) 0.0289(5) Uani 1 1 d . . . . .
H13 H 0.882438 0.484829 0.162955 0.035 Uiso 1 1 calc R U . . .
C14 C 0.8456(2) 0.38175(14) 0.1493(3) 0.0324(6) Uani 1 1 d . . . . .
H14 H 0.894711 0.371208 0.082745 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7823(2) 0.32986(13) 0.1991(3) 0.0298(5) Uani 1 1 d . . . . .
H15 H 0.789300 0.283533 0.168378 0.036 Uiso 1 1 calc R U . . .
C16 C 0.7084(2) 0.34501(12) 0.2938(3) 0.0245(5) Uani 1 1 d . . . . .
H16 H 0.664446 0.309029 0.326942 0.029 Uiso 1 1 calc R U . . .
C17 C 0.6548(2) 0.33682(10) 0.6608(3) 0.0187(4) Uani 1 1 d . . . . .
C18 C 0.7901(2) 0.31962(11) 0.6971(3) 0.0227(4) Uani 1 1 d . . . . .
H18 H 0.843258 0.347884 0.657515 0.027 Uiso 1 1 calc R U . . .
C19 C 0.8469(2) 0.26162(11) 0.7905(3) 0.0272(5) Uani 1 1 d . . . . .
H19 H 0.938435 0.250219 0.813322 0.033 Uiso 1 1 calc R U . . .
C20 C 0.7716(2) 0.22002(11) 0.8511(3) 0.0276(5) Uani 1 1 d . . . . .
H20 H 0.810835 0.180094 0.914136 0.033 Uiso 1 1 calc R U . . .
C21 C 0.6388(2) 0.23722(12) 0.8189(3) 0.0264(5) Uani 1 1 d . . . . .
H21 H 0.586847 0.209211 0.860808 0.032 Uiso 1 1 calc R U . . .
C22 C 0.5810(2) 0.29514(11) 0.7257(3) 0.0215(4) Uani 1 1 d . . . . .
H22 H 0.490057 0.306718 0.705610 0.026 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'
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
C1 N1 C2 108.00(17) . . ?
C1 N1 H1 125.8(17) . . ?
C2 N1 H1 126.0(17) . . ?
C1 N2 C3 105.82(16) . . ?
N2 C1 N1 111.27(17) . . ?
N2 C1 C4 126.55(18) . . ?
N1 C1 C4 122.06(18) . . ?
N1 C2 C3 105.40(17) . . ?
N1 C2 C11 120.41(18) . . ?
C3 C2 C11 134.09(19) . . ?
C2 C3 N2 109.48(17) . . ?
C2 C3 C17 130.60(18) . . ?
N2 C3 C17 119.88(17) . . ?
C9 C4 C5 120.6(2) . . ?
C9 C4 C1 117.27(19) . . ?
C5 C4 C1 122.09(19) . . ?
C6 C5 C4 117.4(2) . . ?
C6 C5 C10 119.8(2) . . ?
C4 C5 C10 122.8(2) . . ?
C7 C6 C5 121.9(2) . . ?
C7 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C8 C7 C6 120.2(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.5(2) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C8 C9 C4 120.4(2) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 118.79(19) . . ?
C12 C11 C2 120.75(19) . . ?
C16 C11 C2 120.40(19) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C11 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C22 C17 C18 118.12(19) . . ?
C22 C17 C3 119.93(18) . . ?
C18 C17 C3 121.93(19) . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C21 C20 C19 119.4(2) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C20 C21 C22 120.3(2) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C21 C22 C17 121.0(2) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
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 C1 1.354(3) . ?
N1 C2 1.381(3) . ?
N1 H1 0.90(3) . ?
N2 C1 1.327(3) . ?
N2 C3 1.390(3) . ?
C1 C4 1.473(3) . ?
C2 C3 1.383(3) . ?
C2 C11 1.467(3) . ?
C3 C17 1.470(3) . ?
C4 C9 1.397(3) . ?
C4 C5 1.402(3) . ?
C5 C6 1.396(3) . ?
C5 C10 1.507(3) . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.394(3) . ?
C11 C16 1.400(3) . ?
C12 C13 1.391(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C22 1.400(3) . ?
C17 C18 1.402(3) . ?
C18 C19 1.386(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.386(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
