#------------------------------------------------------------------------------
#$Date: 2022-07-23 03:18:52 +0300 (Sat, 23 Jul 2022) $
#$Revision: 276842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/07/7710765.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_7710765
loop_
_publ_author_name
'Barnard, Peter'
'Mather , Joel'
'Wyllie, Jessica Anne'
'Hamilton, Alex'
'Soares da Costa, Tatiana P.'
_publ_section_title
;
 Antibacterial silver and gold complexes of imidazole and 1,2,4-triazole
 derived N-heterocyclic carbenes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01657E
_journal_year                    2022
_chemical_formula_moiety         'I, C9 H10 N3'
_chemical_formula_sum            'C9 H10 I N3'
_chemical_formula_weight         287.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-26
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-07-13 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 131.433(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.83570(10)
_cell_length_b                   12.72860(10)
_cell_length_c                   14.2408(2)
_cell_measurement_reflns_used    16311
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      71.1170
_cell_measurement_theta_min      4.1480
_cell_volume                     1064.87(4)
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      149.99(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Oxford Diffraction SuperNova'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21563
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.237
_diffrn_reflns_theta_min         5.408
_exptl_absorpt_coefficient_mu    23.302
_exptl_absorpt_correction_T_max  0.98425
_exptl_absorpt_correction_T_min  0.98425
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.36a (Rigaku Oxford Diffraction, 2018)
Spherical absorption correction
 using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.328
_refine_diff_density_min         -1.010
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2066
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0559P)²+0.5651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0759
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2045
_reflns_number_total             2066
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt01657e2.cif
_cod_data_source_block           1e
_cod_original_cell_volume        1064.87(3)
_cod_database_code               7710765
_shelx_shelxl_version_number     2014/7
_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_max   0.653
_shelx_estimated_absorpt_t_min   0.456
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C2(H2), C4(H4), C6(H6), C8(H8), C7(H7)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
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'
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
I1 I 0.50152(3) 0.56031(2) 0.67067(2) 0.02583(11) Uani 1 1 d . . . . .
N1 N 0.3862(4) 0.76112(17) 0.4294(2) 0.0240(4) Uani 1 1 d . . . . .
N2 N 0.0710(4) 0.68869(18) 0.3518(2) 0.0277(5) Uani 1 1 d . . . . .
N3 N 0.2498(4) 0.84076(19) 0.4127(3) 0.0342(5) Uani 1 1 d . . . . .
C3 C 0.6183(5) 0.7811(2) 0.4884(2) 0.0249(5) Uani 1 1 d . . . . .
C1 C 0.2788(5) 0.6697(2) 0.3937(2) 0.0250(5) Uani 1 1 d . . . . .
H1 H 0.3383 0.6033 0.3973 0.030 Uiso 1 1 calc R U . . .
C5 C 0.9928(5) 0.7169(3) 0.5935(3) 0.0360(6) Uani 1 1 d . . . . .
H5 H 1.0968 0.6602 0.6247 0.043 Uiso 1 1 calc R U . . .
C2 C 0.0607(5) 0.7929(3) 0.3658(3) 0.0350(6) Uani 1 1 d . . . . .
H2 H -0.0689 0.8273 0.3440 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7673(5) 0.6967(2) 0.5356(3) 0.0300(6) Uani 1 1 d . . . . .
H4 H 0.7166 0.6270 0.5284 0.036 Uiso 1 1 calc R U . . .
C6 C 1.0664(6) 0.8195(3) 0.6061(3) 0.0374(7) Uani 1 1 d . . . . .
H6 H 1.2207 0.8329 0.6465 0.045 Uiso 1 1 calc R U . . .
C8 C 0.6882(5) 0.8832(2) 0.4986(3) 0.0320(6) Uani 1 1 d . . . . .
H8 H 0.5829 0.9397 0.4642 0.038 Uiso 1 1 calc R U . . .
C7 C 0.9145(6) 0.9018(3) 0.5598(3) 0.0389(7) Uani 1 1 d . . . . .
H7 H 0.9661 0.9719 0.5701 0.047 Uiso 1 1 calc R U . . .
C9 C -0.1021(5) 0.6092(3) 0.3118(3) 0.0387(7) Uani 1 1 d . . . . .
H9A H -0.0980 0.5530 0.2663 0.058 Uiso 1 1 calc R U . . .
H9B H -0.2531 0.6420 0.2569 0.058 Uiso 1 1 calc R U . . .
H9C H -0.0704 0.5798 0.3856 0.058 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 0.0181 0.0091 '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'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
N3 N1 C3 120.7(2) . . ?
C1 N1 N3 110.9(2) . . ?
C1 N1 C3 128.2(2) . . ?
C1 N2 C2 106.6(2) . . ?
C1 N2 C9 126.0(3) . . ?
C2 N2 C9 127.1(3) . . ?
C2 N3 N1 103.5(2) . . ?
C4 C3 N1 118.7(2) . . ?
C8 C3 N1 119.3(2) . . ?
C8 C3 C4 121.9(3) . . ?
N1 C1 N2 106.9(2) . . ?
N1 C1 H1 126.6 . . ?
N2 C1 H1 126.6 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.3(3) . . ?
N2 C2 H2 124.0 . . ?
N3 C2 N2 112.1(3) . . ?
N3 C2 H2 124.0 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C5 C6 H6 120.1 . . ?
C7 C6 C5 119.9(3) . . ?
C7 C6 H6 120.1 . . ?
C3 C8 H8 120.6 . . ?
C3 C8 C7 118.7(3) . . ?
C7 C8 H8 120.6 . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
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 N3 1.375(3) . ?
N1 C3 1.434(4) . ?
N1 C1 1.325(3) . ?
N2 C1 1.334(4) . ?
N2 C2 1.352(4) . ?
N2 C9 1.471(4) . ?
N3 C2 1.304(4) . ?
C3 C4 1.389(4) . ?
C3 C8 1.381(4) . ?
C1 H1 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.392(4) . ?
C5 C6 1.390(5) . ?
C2 H2 0.9500 . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.382(5) . ?
C8 H8 0.9500 . ?
C8 C7 1.384(5) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N3 C2 N2 -0.3(3) . . . . ?
N1 C3 C4 C5 -179.5(3) . . . . ?
N1 C3 C8 C7 177.6(3) . . . . ?
N3 N1 C3 C4 161.9(3) . . . . ?
N3 N1 C3 C8 -17.1(4) . . . . ?
N3 N1 C1 N2 0.9(3) . . . . ?
C3 N1 N3 C2 -175.6(2) . . . . ?
C3 N1 C1 N2 175.6(2) . . . . ?
C3 C8 C7 C6 2.3(4) . . . . ?
C1 N1 N3 C2 -0.4(3) . . . . ?
C1 N1 C3 C4 -12.4(4) . . . . ?
C1 N1 C3 C8 168.6(3) . . . . ?
C1 N2 C2 N3 0.8(3) . . . . ?
C5 C6 C7 C8 -1.3(5) . . . . ?
C2 N2 C1 N1 -1.0(3) . . . . ?
C4 C3 C8 C7 -1.3(4) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C6 C5 C4 C3 1.5(4) . . . . ?
C8 C3 C4 C5 -0.5(4) . . . . ?
C9 N2 C1 N1 -174.8(2) . . . . ?
C9 N2 C2 N3 174.5(3) . . . . ?
