Dual Targeting of the Cancer Antioxidant Network with Naphthoquinone Fused Gold(I) N-heterocyclic Carbene Complexes
McCall, Rebecca; Miles, Meredith; Lascuna, Paul; Burney, Briana; Patel, Zarana; Sidoran, Kevin; Sittaramane, Vinoth; Kocerha, Jannet; Grossie, David; Sessler, Jonathan L.; Arumugam, Kuppuswamy; Arambula, Jonathan; Chem. Sci.  (2017) –; doi:10.1039/C7SC02153D

data_1546585
_publ_section_title
;
 Dual Targeting of the Cancer Antioxidant Network with Naphthoquinone
 Fused Gold(I) N-heterocyclic Carbene Complexes
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC02153D
_journal_year                    2017
_chemical_formula_moiety         'C58 H52 Au N4 O4, Ag Cl2'
_chemical_formula_sum            'C58 H52 Ag Au Cl2 N4 O4'
_chemical_formula_weight         1244.77
_chemical_name_common            '[Bis(NQMes)Au][AgCl2]'
_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
_audit_creation_date             2016-11-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_audit_update_record
;
2016-12-01 deposited with the CCDC.
2017-07-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.040(3)
_cell_length_b                   16.674(2)
_cell_length_c                   14.2441(17)
_cell_measurement_reflns_used    9524
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.118
_cell_measurement_theta_min      2.216
_cell_volume                     5234.6(11)
_computing_cell_refinement       'APEX2. Ver. 2014.11-0.  (Bruker-AXS, 2014a)'
_computing_data_collection       'APEX2. Ver. 2014.11-0.  (Bruker-AXS, 2014a)'
_computing_data_reduction        'SAINT. Ver. 8.34A. (Bruker-AXS, 2014b)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
;
Olex2 (Dolomanov et al., 2009), Platon (Spek, 2009), Mercury (Macrae et al, 2006)'
;
_computing_structure_refinement  'XL. Ver. 2014/7. (Sheldrick, 2015b)'
_computing_structure_solution    'XT. Ver. 2014/4. (Sheldrick, 2015a)'
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            120752
_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         28.320
_diffrn_reflns_theta_min         1.531
_exptl_absorpt_coefficient_mu    3.326
_exptl_absorpt_correction_T_max  0.8113
_exptl_absorpt_correction_T_min  0.5900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1777 before and 0.0857 after correction.
The Ratio of minimum to maximum transmission is 0.4129.
The \l/2 correction factor is 0.0040.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.093
_refine_diff_density_max         1.040
_refine_diff_density_min         -1.742
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.410(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     644
_refine_ls_number_reflns         13013
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0297
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0415P)^2^+2.8359P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0645
_refine_ls_wR_factor_ref         0.0672
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                11671
_reflns_number_total             13013
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc02153d2.cif
_cod_data_source_block           compound_1
_cod_original_cell_volume        5234.7(11)
_cod_database_code               1546585
_publcif_datablock.id            {7259a5ee-e9c8-4c69-b841-77786af0f793}
_shelx_estimated_absorpt_t_max   0.747
_shelx_estimated_absorpt_t_min   0.553
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.590(5) 0.410(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C16(H16), C23(H23), C25(H25),
 C34(H34), C35(H35), C36(H36), C37(H37), C43(H43), C45(H45), C52(H52), C54(H54)
3.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C47(H47A,H47B,H47C), C48(H48A,
 H48B,H48C), C49(H49A,H49B,H49C), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C),
 C58(H58A,H58B,H58C)
;
_shelx_res_checksum              72074
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'