A novel aminotriazole-based NHC complex for the design of gold(i) anti-cancer agents: synthesis and biological evaluation
Serebryanskaya, T. V.; Zolotarev, A. A.; Ott, I.; Med. Chem. Commun. 6 (2015) 1186–; doi:10.1039/C5MD00185D

data_7117165
_publ_section_title
;
 A novel aminotriazole-based NHC complex for the design of gold(i)
 anti-cancer agents: synthesis and biological evaluation
;
_journal_issue                   6
_journal_name_full               'Med. Chem. Commun.'
_journal_page_first              1186
_journal_paper_doi               10.1039/C5MD00185D
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C20 H36 Au N8, Cl O4'
_chemical_formula_sum            'C20 H36 Au Cl N8 O4'
_chemical_formula_weight         684.98
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-03-23 deposited with the CCDC.
2015-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5632(4)
_cell_length_b                   12.4279(4)
_cell_length_c                   19.2238(9)
_cell_measurement_reflns_used    11279
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.8650
_cell_measurement_theta_min      3.5820
_cell_volume                     2762.58(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -18.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0037   38.0000  -90.0000 53

  2 omega -126.00  -36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0037  178.0000   90.0000 90

  3 omega -116.00  -44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0037  -77.0000  -30.0000 72

  4 omega   68.00  122.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0037  178.0000 -180.0000 54

  5 omega   32.00   57.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 25

  6 omega   38.00   94.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 56

  7 omega   48.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 61

  8 omega   81.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   30.0000 28

  9 omega   38.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 49

 10 omega  122.00  149.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000   30.0000 27

 11 omega   84.00  117.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -30.0000 33

 12 omega   62.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   30.0000 47

 13 omega   66.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  120.0000 27

 14 omega   39.00   73.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  150.0000 34

 15 omega   45.00  116.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000    0.0000 71

 16 omega   88.00  125.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 37

 17 omega   55.00  104.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -180.0000 49

 18 omega   72.00   98.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -180.0000 26

 19 omega   43.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 42

 20 omega   65.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 32

 21 omega   83.00  124.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 41

 22 omega  126.00  153.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 27

 23 omega   48.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000    0.0000 45

 24 omega   55.00   85.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 30

 25 omega   69.00   97.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 28

 26 omega  104.00  133.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 29

 27 omega   78.00  103.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -21.0000  102.9286 25

 28 omega  118.00  168.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  120.0000 50

 29 omega   89.00  114.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -107.0000  -59.0000 25

 30 omega   66.00   93.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 27

 31 omega   33.00   69.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -21.0000  102.9286 36

 32 omega  -83.00  -33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0037  -38.0000    0.0000 50

 33 omega  -90.00  -47.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0037  -57.0000    0.0000 43

 34 omega  -38.00   14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0037   38.0000  150.0000 52

 35 omega  -98.00   -8.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0037  -77.0000    0.0000 90

 36 omega  -61.00  -15.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0037  -57.0000   30.0000 46

 37 omega  -44.00  -19.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0037  -38.0000 -150.0000 25

 38 omega   25.00   53.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0037   38.0000    0.0000 28

 39 omega   83.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   60.0000   16.3269 26

 40 omega   81.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   70.0000   17.5311 27

 41 omega   88.00  115.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   36.0000   64.4862 27

 42 omega   31.00   76.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    5.0000  138.5558 45

 43 omega   67.00   94.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   19.0000  103.9200 27

 44 omega  108.00  135.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   50.0000  151.3007 27

 45 omega  123.00  150.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 27

 46 omega   81.00  108.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   70.0000   50.7579 27

 47 omega   83.00  110.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   69.0000   21.4597 27

 48 omega  119.00  146.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   65.0000   63.4958 27

 49 omega   79.00  106.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 27

 50 omega   84.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 25

 51 omega   84.00  120.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 36

 52 omega   79.00  105.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 26

 53 omega   37.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 34

 54 omega   84.00  111.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 27

 55 omega  143.00  171.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000    0.0000 28

 56 omega   80.00  101.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 21
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0197223000
_diffrn_orient_matrix_UB_12      0.0319620000
_diffrn_orient_matrix_UB_13      0.0765397000
_diffrn_orient_matrix_UB_21      0.1301574000
_diffrn_orient_matrix_UB_22      0.0136447000
_diffrn_orient_matrix_UB_23      -0.0145612000
_diffrn_orient_matrix_UB_31      -0.0201220000
_diffrn_orient_matrix_UB_32      0.1190080000
_diffrn_orient_matrix_UB_33      -0.0189077000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1207
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_laue_measured_fraction_full 0.995
_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       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26372
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.482
_diffrn_reflns_theta_min         3.556
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.647
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         6.182
_refine_diff_density_min         -2.200
_refine_diff_density_rms         0.301
_refine_ls_abs_structure_details
;
 Flack x determined using 1606 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         4486
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0855
_refine_ls_R_factor_gt           0.0804
_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/[\s^2^(Fo^2^)+(0.0756P)^2^+126.8455P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2039
_refine_ls_wR_factor_ref         0.2075
_reflns_Friedel_coverage         0.939
_reflns_friedel_fraction_full    0.997
_reflns_friedel_fraction_max     1.000
_reflns_number_gt                4127
_reflns_number_total             4486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5md00185d2.cif
_cod_data_source_block           Au(NHC)2ClO4
_cod_depositor_comments          'Adding full bibliography for 7117165.cif.'
_cod_database_code               7117165
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C20 H36 Au Cl N8 O4'
_reflns_odcompleteness_completeness 94.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H10A(0.047) H10B(0.047) H10C(0.047) H8AA(0.047) H8AB(0.047)
 H8AC(0.047) H13A(0.047) H13B(0.047) H13C(0.047) H14A(0.047) H14B(0.047)
 H14C(0.047) H12A(0.047) H12B(0.047) H12C(0.047) H13D(0.047) H13E(0.047)
 H13F(0.047) H14D(0.047) H14E(0.047) H14F(0.047) H12D(0.047) H12E(0.047)
 H12F(0.047) H9AA(0.047) H9AB(0.047) H9AC(0.047) H10D(0.047) H10E(0.047)
 H10F(0.047) H8A(0.047) H8B(0.047) H8C(0.047) H9A(0.047) H9B(0.047) H9C(0.047)
 Fixed X: H10A(0.7935) H10B(0.7213) H10C(0.7797) H8AA(0.5852) H8AB(0.5266)
 H8AC(0.4792) H13A(0.6176) H13B(0.6237) H13C(0.543) H14A(0.8851) H14B(0.8108)
 H14C(0.8504) H12A(0.6269) H12B(0.7018) H12C(0.7642) H13D(0.3536) H13E(0.2577)
 H13F(0.2272) H14D(0.0536) H14E(0.1171) H14F(0.1007) H12D(0.2883) H12E(0.3127)
 H12F(0.3915) H9AA(0.4996) H9AB(0.5604) H9AC(0.6236) H10D(0.3319) H10E(0.3623)
 H10F(0.4439) H8A(0.4245) H8B(0.3509) H8C(0.3002) H9A(0.1212) H9B(0.1742)
 H9C(0.1338)
 Fixed Y: H10A(0.6924) H10B(0.794) H10C(0.7137) H8AA(0.6927) H8AB(0.7676)
 H8AC(0.6482) H13A(0.2663) H13B(0.2612) H13C(0.3484) H14A(0.3783) H14B(0.2754)
 H14C(0.2897) H12A(0.509) H12B(0.4367) H12C(0.5239) H13D(0.4525) H13E(0.4081)
 H13F(0.5047) H14D(0.3606) H14E(0.2869) H14F(0.2441) H12D(0.2221) H12E(0.2186)
 H12F(0.2917) H9AA(0.6115) H9AB(0.7233) H9AC(0.6121) H10D(0.6807) H10E(0.7862)
 H10F(0.6825) H8A(0.6605) H8B(0.7695) H8C(0.661) H9A(0.6839) H9B(0.7918)
 H9C(0.6961)
 Fixed Z: H10A(0.4881) H10B(0.4612) H10C(0.4065) H8AA(0.3516) H8AB(0.4094)
 H8AC(0.3967) H13A(0.2442) H13B(0.1611) H13C(0.1985) H14A(0.1721) H14B(0.1496)
 H14C(0.2288) H12A(0.1522) H12B(0.1001) H12C(0.1485) H13D(0.4608) H13E(0.5136)
 H13F(0.4617) H14D(0.4256) H14E(0.4822) H14F(0.4043) H12D(0.362) H12E(0.4439)
 H12F(0.3944) H9AA(0.5184) H9AB(0.5377) H9AC(0.5553) H10D(0.2939) H10E(0.2498)
 H10F(0.2451) H8A(0.1193) H8B(0.1155) H8C(0.0827) H9A(0.1549) H9B(0.1873)
 H9C(0.2374)
;
_olex2_submission_special_instructions 'No special instructions were received'