#------------------------------------------------------------------------------
#$Date: 2025-04-03 08:32:21 +0300 (Thu, 03 Apr 2025) $
#$Revision: 298703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/53/7705335.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_7705335
loop_
_publ_author_name
'Li, Zili'
'Mackie, Emily R. R.'
'Ramkissoon, Pria'
'Mather, Joel C.'
'Wiratpruk, Nuchareenat'
'Soares da Costa, Tatiana P.'
'Barnard, Peter J.'
_publ_section_title
;
 Synthesis, conformational analysis and antibacterial activity of
 Au(I)-Ag(I) and Au(I)-Hg(II) heterobimetallic N-heterocyclic carbene
 complexes.
;
_journal_issue                   36
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12820
_journal_page_last               12834
_journal_paper_doi               10.1039/d0dt02225j
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C9 H13 N4, I'
_chemical_formula_sum            'C9 H13 I N4'
_chemical_formula_weight         304.13
_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     direct
_audit_creation_date             2020-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-17 deposited with the CCDC.	2020-09-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 124.136(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.8428(6)
_cell_length_b                   11.5230(5)
_cell_length_c                   17.2878(15)
_cell_measurement_reflns_used    5123
_cell_measurement_temperature    133.0(4)
_cell_measurement_theta_max      76.5850
_cell_measurement_theta_min      4.9220
_cell_volume                     1128.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      133.0(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3309
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00  70.00   1.00    1.00    --   41.58 -57.00   0.00   94
  2  ω     16.00  42.00   1.00    1.00    --   41.58 -77.00   0.00   26
  3  ω      2.00  95.00   1.00    1.00    --   41.58-125.00 -90.00   93
  4  ω     43.00  75.00   1.00    4.00    --  112.00 -61.00-120.00   32
  5  ω     89.00 115.00   1.00    4.00    --  112.00 -61.00-120.00   26
  6  ω     76.00 104.00   1.00    4.00    --  112.00-111.00 -60.00   28
  7  ω     89.00 116.00   1.00    4.00    --  112.00-111.00-150.00   27
  8  ω     41.00 115.00   1.00    4.00    --  112.00-111.00 -30.00   74
  9  ω     57.00 111.00   1.00    4.00    --  112.00-111.00  60.00   54
 10  ω     74.00 115.00   1.00    4.00    --  112.00-111.00 120.00   41
 11  ω     56.00 136.00   1.00    4.00    --  112.00 -45.00 120.00   80
 12  ω    122.00 148.00   1.00    4.00    --  112.00  15.00   0.00   26
 13  ω     79.00 130.00   1.00    4.00    --  112.00  77.00  90.00   51
 14  ω     95.00 121.00   1.00    4.00    --  112.00  61.00 150.00   26
 15  ω     65.00  96.00   1.00    4.00    --  112.00  15.00   0.00   31
 16  ω     36.00 127.00   1.00    4.00    --  112.00 -30.00 -90.00   91
 17  ω     92.00 158.00   1.00    4.00    --  112.00  45.00-180.00   66
 18  ω    113.00 155.00   1.00    4.00    --  112.00  61.00-150.00   42
 19  ω     81.00 157.00   1.00    4.00    --  112.00 111.00-150.00   76
 20  ω     63.00 128.00   1.00    4.00    --  112.00  15.00-180.00   65
 21  ω     36.00  62.00   1.00    4.00    --  112.00-111.00 -60.00   26
 22  ω     57.00  93.00   1.00    4.00    --  112.00-111.00  30.00   36
 23  ω     36.00  97.00   1.00    4.00    --  112.00-111.00  90.00   61
 24  ω     36.00 142.00   1.00    4.00    --  112.00 -77.00 120.00  106
 25  ω     28.00 116.00   1.00    1.00    --   41.58  38.00 150.00   88
 26  ω     22.00  58.00   1.00    1.00    --   41.58  57.00 -30.00   36
 27  ω    -33.00  -6.00   1.00    1.00    --   41.58 -77.00   0.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0382959000
_diffrn_orient_matrix_UB_12      0.1321592000
_diffrn_orient_matrix_UB_13      -0.0132979000
_diffrn_orient_matrix_UB_21      -0.0046491000
_diffrn_orient_matrix_UB_22      0.0069389000
_diffrn_orient_matrix_UB_23      0.0879630000
_diffrn_orient_matrix_UB_31      0.2692696000
_diffrn_orient_matrix_UB_32      0.0188473000
_diffrn_orient_matrix_UB_33      0.0606802000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9269
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.480
_diffrn_reflns_theta_min         4.928
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    22.055
_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 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.626
_refine_diff_density_min         -1.334
_refine_diff_density_rms         0.136
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0581P)²+0.8684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0842
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2138
_reflns_number_total             2314
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt02225j2.cif
_cod_data_source_block           10a
_cod_depositor_comments
;
Adding full bibliography for 7705334--7705337.cif.

2025-04-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C18 H26 I2 N8'
_cod_original_formula_weight         608.27
_cod_original_formula_moiety         '2(C9 H13 N4), 2(I)'
_cod_original_formula_units_Z            2
_cod_database_code               7705335
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H20 N12 Br2'
_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   0.667
_shelx_estimated_absorpt_t_min   0.472
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_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'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.939
_oxdiff_exptl_absorpt_empirical_full_min 0.692
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
C1 C 0.8846(6) 0.2658(2) 0.6449(2) 0.0197(6) Uani 1 1 d . . . . .
H1 H 0.8505 0.2150 0.6776 0.024 Uiso 1 1 calc R . . . .
C2 C 0.9382(5) 0.4259(3) 0.5897(2) 0.0250(6) Uani 1 1 d . . . . .
H2 H 0.9481 0.5041 0.5788 0.030 Uiso 1 1 calc R . . . .
C3 C 0.9741(5) 0.3343(3) 0.5499(2) 0.0241(6) Uani 1 1 d . . . . .
H3 H 1.0133 0.3375 0.5065 0.029 Uiso 1 1 calc R . . . .
C4 C 0.4625(6) 0.6230(3) 0.7196(2) 0.0279(6) Uani 1 1 d . . . . .
H4 H 0.4613 0.6777 0.6797 0.033 Uiso 1 1 calc R . . . .
C5 C 0.4894(6) 0.4576(3) 0.7860(2) 0.0268(6) Uani 1 1 d . . . . .
H5 H 0.5091 0.3793 0.8017 0.032 Uiso 1 1 calc R . . . .
C6 C 0.4419(6) 0.5443(3) 0.8260(2) 0.0288(7) Uani 1 1 d . . . . .
H6 H 0.4231 0.5346 0.8749 0.035 Uiso 1 1 calc R . . . .
C7 C 0.8247(5) 0.4475(2) 0.70538(19) 0.0216(5) Uani 1 1 d . . . . .
H7A H 0.8859 0.5258 0.7142 0.026 Uiso 1 1 calc R . . . .
H7B H 0.8974 0.4118 0.7664 0.026 Uiso 1 1 calc R . . . .
C8 C 0.5591(5) 0.4517(3) 0.6573(2) 0.0225(6) Uani 1 1 d . . . . .
H8A H 0.4874 0.4935 0.5987 0.027 Uiso 1 1 calc R . . . .
H8B H 0.4960 0.3735 0.6436 0.027 Uiso 1 1 calc R . . . .
C9 C 0.9454(6) 0.1174(3) 0.5560(2) 0.0291(7) Uani 1 1 d . . . . .
H9A H 0.9929 0.0644 0.6065 0.044 Uiso 1 1 calc GR . . . .
H9B H 1.0552 0.1132 0.5382 0.044 Uiso 1 1 calc GR . . . .
H9C H 0.7905 0.0970 0.5036 0.044 Uiso 1 1 calc GR . . . .
I1 I 0.28039(3) 0.24303(2) 0.42402(2) 0.02147(11) Uani 1 1 d . . . . .
N1 N 0.8842(4) 0.3809(2) 0.64929(15) 0.0186(4) Uani 1 1 d . . . . .
N2 N 0.9416(5) 0.2356(2) 0.5860(2) 0.0191(5) Uani 1 1 d . . . . .
N3 N 0.5023(4) 0.5091(2) 0.71723(17) 0.0197(5) Uani 1 1 d . . . . .
N4 N 0.4255(5) 0.6484(3) 0.78434(19) 0.0339(6) Uani 1 1 d . . . . .
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
N2 C1 N1 108.5(3) . . ?
C3 C2 N1 106.6(3) . . ?
C2 C3 N2 107.1(3) . . ?
N4 C4 N3 112.5(3) . . ?
C6 C5 N3 105.9(3) . . ?
C5 C6 N4 110.4(3) . . ?
N1 C7 C8 110.3(2) . . ?
N3 C8 C7 110.0(2) . . ?
C1 N1 C2 108.9(2) . . ?
C1 N1 C7 124.9(3) . . ?
C2 N1 C7 126.2(2) . . ?
C1 N2 C3 108.9(2) . . ?
C1 N2 C9 126.1(3) . . ?
C3 N2 C9 124.7(3) . . ?
C4 N3 C5 106.4(3) . . ?
C4 N3 C8 127.2(3) . . ?
C5 N3 C8 126.3(3) . . ?
C4 N4 C6 104.8(3) . . ?
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
C1 N1 1.329(4) . ?
C1 N2 1.324(4) . ?
C2 C3 1.356(4) . ?
C2 N1 1.376(4) . ?
C3 N2 1.374(4) . ?
C4 N3 1.346(4) . ?
C4 N4 1.312(4) . ?
C5 C6 1.355(5) . ?
C5 N3 1.375(4) . ?
C6 N4 1.371(5) . ?
C7 C8 1.517(4) . ?
C7 N1 1.462(3) . ?
C8 N3 1.454(4) . ?
C9 N2 1.463(4) . ?
