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#$Date: 2025-08-21 17:09:30 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301850 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/20/7042007.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_7042007
loop_
_publ_author_name
'Diehl, Tobias'
'Krause, Melanie T. S.'
'Ueberlein, Sven'
'Becker, Stefanie'
'Trommer, Aline'
'Schnakenburg, Gregor'
'Engeser, Marianne'
_publ_section_title
;
 Synthesis of hydroxyl-functionalized N-heterocyclic carbene gold(i)
 complexes and peptide conjugates.
;
_journal_issue                   9
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2988
_journal_page_last               2997
_journal_paper_doi               10.1039/c6dt04834j
_journal_volume                  46
_journal_year                    2017
_chemical_formula_moiety         'C22 H26 Au N4 O2, Br'
_chemical_formula_sum            'C22 H26 Au Br N4 O2'
_chemical_formula_weight         655.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-10-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2017-01-18 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.142(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.4734(10)
_cell_length_b                   14.2194(10)
_cell_length_c                   11.8904(8)
_cell_measurement_reflns_used    5855
_cell_measurement_temperature    123
_cell_measurement_theta_max      29.26
_cell_measurement_theta_min      2.81
_cell_volume                     2264.9(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1547
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11112
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.81
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.00
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    8.285
_exptl_absorpt_correction_T_max  0.5082
_exptl_absorpt_correction_T_min  0.2484
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plank
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         4.917
_refine_diff_density_min         -11.835
_refine_diff_density_rms         0.481
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.368
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2222
_refine_ls_number_restraints     55
_refine_ls_restrained_S_all      1.354
_refine_ls_R_factor_all          0.1482
_refine_ls_R_factor_gt           0.1461
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0001P)²+623.7133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3493
_refine_ls_wR_factor_ref         0.3503
_reflns_number_gt                2145
_reflns_number_total             2222
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6dt04834j2.cif
_cod_data_source_block           3716
_cod_depositor_comments
'Adding full bibliography for 7042003--7042010.cif.'
_cod_database_code               7042007
_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, All O(H) groups
2. Restrained distances
 C10-C11
 1.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C6) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C11)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N2) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
4.d Idealised tetrahedral OH refined as rotating group:
 O(H)
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 '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_calc_flag
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Au Au 0.0000 0.31519(12) 0.2500 0.0326(5) Uani 1 d 2 S T P
O O 0.135(2) 0.105(2) -0.042(2) 0.062(8) Uani 1 d 1 . . .
H H 0.1320 0.0709 0.0152 0.093 Uiso 1 calc 1 GR . .
N1 N -0.080(2) 0.2483(17) 0.016(2) 0.037(6) Uani 1 d 1 . . .
N2 N -0.1424(18) 0.3849(19) 0.056(2) 0.035(6) Uani 1 d 1 . U .
C1 C -0.079(2) 0.314(2) 0.094(2) 0.036(6) Uani 1 d 1 . . .
C2 C -0.143(3) 0.272(3) -0.079(3) 0.047(8) Uani 1 d 1 . U .
C3 C -0.183(2) 0.357(2) -0.059(3) 0.040(7) Uani 1 d 1 . U .
C4 C -0.166(3) 0.223(3) -0.182(3) 0.051(9) Uani 1 d 1 . U .
H4 H -0.1364 0.1645 -0.1992 0.061 Uiso 1 calc 1 R . .
C5 C -0.237(4) 0.271(3) -0.258(4) 0.070(12) Uani 1 d 1 . U .
H5 H -0.2565 0.2417 -0.3288 0.084 Uiso 1 calc 1 R . .
C6 C -0.281(4) 0.353(3) -0.237(4) 0.071(12) Uani 1 d 1 . U .
H6 H -0.3289 0.3791 -0.2926 0.085 Uiso 1 calc 1 R . .
C7 C -0.256(3) 0.400(3) -0.137(3) 0.049(8) Uani 1 d 1 . U .
C8 C -0.012(3) 0.165(2) 0.023(3) 0.060(13) Uani 1 d 1 . . .
H8A H -0.0461 0.1115 -0.0175 0.072 Uiso 1 calc 1 R . .
H8B H 0.0054 0.1471 0.1029 0.072 Uiso 1 calc 1 R . .
C9 C 0.081(2) 0.189(2) -0.030(3) 0.043(7) Uani 1 d 1 . U .
H9A H 0.0636 0.2189 -0.1048 0.051 Uiso 1 calc 1 R . .
H9B H 0.1222 0.2343 0.0187 0.051 Uiso 1 calc 1 R . .
C10 C -0.165(3) 0.469(2) 0.108(4) 0.054(10) Uani 1 d 1 D . .
H10A H -0.1653 0.4582 0.1898 0.065 Uiso 1 calc 1 R . .
H10B H -0.2332 0.4891 0.0773 0.065 Uiso 1 calc 1 R . .
C11 C -0.093(4) 0.547(3) 0.090(5) 0.082(14) Uani 1 d 1 D U .
H11A H -0.0253 0.5267 0.1166 0.123 Uiso 1 calc 1 GR . .
H11B H -0.1104 0.6027 0.1322 0.123 Uiso 1 calc 1 GR . .
H11C H -0.0972 0.5621 0.0091 0.123 Uiso 1 calc 1 GR . .
Br Br 0.0000 0.0185(4) -0.2500 0.078(2) Uani 1 d 2 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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 '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
C1 Au C1 178.8(19) 2
C9 O H 109.5 .
C1 N1 C2 111(3) .
C1 N1 C8 125(3) .
C2 N1 C8 124(3) .
C1 N2 C3 106(2) .
C1 N2 C10 130(3) .
C10 N2 C3 124(3) .
N1 C1 Au 128(2) .
N1 C1 N2 110(3) .
N2 C1 Au 123(2) .
N1 C2 C4 130(3) .
C3 C2 N1 107(3) .
C3 C2 C4 123(3) .
C2 C3 N2 107(3) .
C2 C3 C7 122(3) .
C7 C3 N2 131(3) .
C2 C4 H4 123.8 .
C5 C4 C2 112(4) .
C5 C4 H4 123.8 .
C4 C5 H5 117.2 .
C6 C5 C4 126(5) .
C6 C5 H5 117.2 .
C5 C6 H6 119.6 .
C5 C6 C7 121(4) .
C7 C6 H6 119.6 .
C6 C7 C3 117(4) .
N1 C8 H8A 109.8 .
N1 C8 H8B 109.8 .
N1 C8 C9 109(3) .
H8A C8 H8B 108.2 .
C9 C8 H8A 109.8 .
C9 C8 H8B 109.8 .
O C9 C8 108(3) .
O C9 H9A 110.1 .
O C9 H9B 110.1 .
C8 C9 H9A 110.1 .
C8 C9 H9B 110.1 .
H9A C9 H9B 108.4 .
N2 C10 H10A 108.9 .
N2 C10 H10B 108.9 .
N2 C10 C11 113(3) .
H10A C10 H10B 107.7 .
C11 C10 H10A 108.9 .
C11 C10 H10B 108.9 .
C10 C11 H11A 109.5 .
C10 C11 H11B 109.5 .
C10 C11 H11C 109.5 .
H11A C11 H11B 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Au C1 2.04(3) 2
Au C1 2.04(3) .
O H 0.8400 .
O C9 1.42(4) .
N1 C1 1.31(4) .
N1 C2 1.39(4) .
N1 C8 1.49(4) .
N2 C1 1.37(4) .
N2 C3 1.47(4) .
N2 C10 1.40(5) .
C2 C3 1.36(5) .
C2 C4 1.42(5) .
C3 C7 1.41(5) .
C4 H4 0.9500 .
C4 C5 1.42(6) .
C5 H5 0.9500 .
C5 C6 1.34(6) .
C6 H6 0.9500 .
C6 C7 1.37(6) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C8 C9 1.50(6) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C10 C11 1.499(10) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 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
N1 C2 C3 N2 -1(4) .
N1 C2 C3 C7 -177(3) .
N1 C2 C4 C5 178(4) .
N1 C8 C9 O -169(3) .
N2 C3 C7 C6 -177(4) .
C1 Au C1 N1 -27(3) 2
C1 Au C1 N2 152(2) 2
C1 N1 C2 C3 1(4) .
C1 N1 C2 C4 179(4) .
C1 N1 C8 C9 -90(4) .
C1 N2 C3 C2 2(3) .
C1 N2 C3 C7 176(4) .
C1 N2 C10 C11 85(5) .
C2 N1 C1 Au 180(2) .
C2 N1 C1 N2 1(4) .
C2 N1 C8 C9 82(4) .
C2 C3 C7 C6 -3(5) .
C2 C4 C5 C6 0(6) .
C3 N2 C1 Au 180(2) .
C3 N2 C1 N1 -1(3) .
C3 N2 C10 C11 -92(4) .
C3 C2 C4 C5 -3(5) .
C4 C2 C3 N2 180(3) .
C4 C2 C3 C7 5(5) .
C4 C5 C6 C7 1(7) .
C5 C6 C7 C3 0(6) .
C8 N1 C1 Au -8(5) .
C8 N1 C1 N2 173(3) .
C8 N1 C2 C3 -172(3) .
C8 N1 C2 C4 6(6) .
C10 N2 C1 Au 2(4) .
C10 N2 C1 N1 -179(3) .
C10 N2 C3 C2 180(3) .
C10 N2 C3 C7 -6(5) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139170165
