#------------------------------------------------------------------------------
#$Date: 2021-08-20 04:12:43 +0300 (Fri, 20 Aug 2021) $
#$Revision: 268148 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/33/7243398.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_7243398
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_formula_moiety         'C19 H20 N2'
_chemical_formula_sum            'C19 H20 N2'
_chemical_formula_weight         276.37
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-07-21 deposited with the CCDC.	2021-08-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.5878(5)
_cell_length_b                   9.2549(3)
_cell_length_c                   20.0075(6)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.38
_cell_volume                     3071.52(16)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonIII'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            61188
_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         27.101
_diffrn_reflns_theta_min         2.036
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8011
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.317
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.167
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0398
_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)+(0.0357P)²+1.4127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0972
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2731
_reflns_number_total             3375
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra05802a2.cif
_cod_data_source_block           i18259
_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_database_code               7243398
_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   0.978
_shelx_estimated_absorpt_t_max   0.988
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
N1 N 0.30994(7) 0.60788(11) 0.27097(5) 0.0182(2) Uani 1 1 d . . . . .
N2 N 0.25898(7) 0.39119(11) 0.28928(5) 0.0179(2) Uani 1 1 d . . . . .
H2 H 0.226381 0.316405 0.286575 0.021 Uiso 1 1 calc R U . . .
C1 C 0.25052(8) 0.51756(13) 0.25631(6) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.35854(8) 0.53552(13) 0.31651(6) 0.0171(3) Uani 1 1 d . . . . .
C3 C 0.32785(8) 0.39981(13) 0.32805(6) 0.0173(3) Uani 1 1 d . . . . .
C4 C 0.17888(8) 0.55381(14) 0.21409(7) 0.0214(3) Uani 1 1 d . . . . .
H4A H 0.192489 0.638251 0.185887 0.026 Uiso 1 1 calc R U . . .
H4AB H 0.134032 0.582726 0.243876 0.026 Uiso 1 1 calc R U . . .
C5 C 0.14954(8) 0.43180(14) 0.16877(7) 0.0212(3) Uani 1 1 d . . . . .
H5A H 0.139687 0.344819 0.196383 0.025 Uiso 1 1 calc R U . . .
H5AB H 0.097527 0.460564 0.148474 0.025 Uiso 1 1 calc R U . . .
C6 C 0.20830(9) 0.39314(16) 0.11324(7) 0.0269(3) Uani 1 1 d . . . . .
H6A H 0.261471 0.370287 0.133071 0.032 Uiso 1 1 calc R U . . .
H6AB H 0.215208 0.477623 0.083430 0.032 Uiso 1 1 calc R U . . .
C7 C 0.17952(10) 0.26444(17) 0.07213(8) 0.0344(4) Uani 1 1 d . . . . .
H7A H 0.127869 0.287952 0.050982 0.052 Uiso 1 1 calc R U . . .
H7B H 0.172694 0.180457 0.101423 0.052 Uiso 1 1 calc R U . . .
H7C H 0.219483 0.242164 0.037561 0.052 Uiso 1 1 calc R U . . .
C8 C 0.42757(8) 0.61108(13) 0.34711(6) 0.0181(3) Uani 1 1 d . . . . .
C9 C 0.47322(8) 0.70834(14) 0.30932(7) 0.0210(3) Uani 1 1 d . . . . .
H9 H 0.460623 0.722811 0.263485 0.025 Uiso 1 1 calc R U . . .
C10 C 0.53673(8) 0.78403(14) 0.33792(7) 0.0241(3) Uani 1 1 d . . . . .
H10 H 0.567041 0.850199 0.311718 0.029 Uiso 1 1 calc R U . . .
C11 C 0.55596(8) 0.76317(15) 0.40463(7) 0.0250(3) Uani 1 1 d . . . . .
H11 H 0.599844 0.813954 0.424095 0.030 Uiso 1 1 calc R U . . .
C12 C 0.51087(8) 0.66789(14) 0.44282(7) 0.0242(3) Uani 1 1 d . . . . .
H12 H 0.523805 0.653870 0.488617 0.029 Uiso 1 1 calc R U . . .
C13 C 0.44696(8) 0.59285(14) 0.41460(7) 0.0210(3) Uani 1 1 d . . . . .
H13 H 0.416115 0.528545 0.441357 0.025 Uiso 1 1 calc R U . . .
C14 C 0.35372(8) 0.27544(13) 0.36838(6) 0.0180(3) Uani 1 1 d . . . . .
C15 C 0.43483(8) 0.23430(14) 0.37154(6) 0.0208(3) Uani 1 1 d . . . . .
H15 H 0.474618 0.291305 0.349827 0.025 Uiso 1 1 calc R U . . .
C16 C 0.45759(9) 0.11092(15) 0.40613(7) 0.0258(3) Uani 1 1 d . . . . .
H16 H 0.512807 0.083999 0.407971 0.031 Uiso 1 1 calc R U . . .
C17 C 0.40000(9) 0.02652(15) 0.43809(7) 0.0275(3) Uani 1 1 d . . . . .
H17 H 0.415581 -0.058853 0.461073 0.033 Uiso 1 1 calc R U . . .
C18 C 0.31982(9) 0.06766(15) 0.43623(7) 0.0254(3) Uani 1 1 d . . . . .
H18 H 0.280394 0.010849 0.458492 0.030 Uiso 1 1 calc R U . . .
C19 C 0.29659(8) 0.19145(14) 0.40202(6) 0.0210(3) Uani 1 1 d . . . . .
H19 H 0.241462 0.219263 0.401472 0.025 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 105.83(10) . . ?
C1 N2 C3 108.05(11) . . ?
C1 N2 H2 126.0 . . ?
C3 N2 H2 126.0 . . ?
N1 C1 N2 111.16(11) . . ?
N1 C1 C4 125.05(11) . . ?
N2 C1 C4 123.56(12) . . ?
C3 C2 N1 109.61(11) . . ?
C3 C2 C8 130.63(11) . . ?
N1 C2 C8 119.63(11) . . ?
C2 C3 N2 105.34(11) . . ?
C2 C3 C14 134.39(12) . . ?
N2 C3 C14 120.25(11) . . ?
C1 C4 C5 114.98(11) . . ?
C1 C4 H4A 108.5 . . ?
C5 C4 H4A 108.5 . . ?
C1 C4 H4AB 108.5 . . ?
C5 C4 H4AB 108.5 . . ?
H4A C4 H4AB 107.5 . . ?
C6 C5 C4 113.79(11) . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5AB 108.8 . . ?
C4 C5 H5AB 108.8 . . ?
H5A C5 H5AB 107.7 . . ?
C5 C6 C7 112.17(12) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6AB 109.2 . . ?
C7 C6 H6AB 109.2 . . ?
H6A C6 H6AB 107.9 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 118.37(12) . . ?
C13 C8 C2 121.48(12) . . ?
C9 C8 C2 120.08(11) . . ?
C10 C9 C8 120.85(13) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 120.08(13) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.70(13) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 120.43(13) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.55(13) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C19 C14 C15 118.59(12) . . ?
C19 C14 C3 120.12(12) . . ?
C15 C14 C3 121.23(12) . . ?
C16 C15 C14 120.52(13) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.34(13) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 C16 119.57(13) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.45(13) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C14 120.51(13) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
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 1.3252(17) . ?
N1 C2 1.3889(16) . ?
N2 C1 1.3501(16) . ?
N2 C3 1.3831(16) . ?
N2 H2 0.8800 . ?
C1 C4 1.4960(18) . ?
C2 C3 1.3748(17) . ?
C2 C8 1.4746(18) . ?
C3 C14 1.4697(17) . ?
C4 C5 1.5278(18) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C6 1.521(2) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C7 1.524(2) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.3983(18) . ?
C8 C9 1.3984(18) . ?
C9 C10 1.3885(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3874(19) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C19 1.3983(19) . ?
C14 C15 1.3998(19) . ?
C15 C16 1.3876(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3890(18) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
