Toward multifunctional anticancer therapeutics: post-synthetic carbonate functionalisation of asymmetric Au(i) bis-N-heterocyclic carbenes.
Sen, Sajal; Perrin, Mark W.; Sedgwick, Adam C.; Dunsky, Evie Y.; Lynch, Vincent M.; He, Xiao-Peng; Sessler, Jonathan L.; Arambula, Jonathan F.; Chemical communications (Cambridge, England) 56 (2020) 7877–7880; doi:10.1039/d0cc03339a

data_7126640
_publ_section_title
;
 Toward multifunctional anticancer therapeutics: post-synthetic carbonate
 functionalisation of asymmetric Au(i) bis-N-heterocyclic carbenes.
;
_journal_issue                   57
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7877
_journal_page_last               7880
_journal_paper_doi               10.1039/d0cc03339a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C50 H62 Au N4 O3, F6 P'
_chemical_formula_sum            'C50 H62 Au F6 N4 O3 P'
_chemical_formula_weight         1108.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-19
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2020-04-26 deposited with the CCDC.	2020-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.130(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.129(4)
_cell_length_b                   14.925(3)
_cell_length_c                   19.946(4)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.45
_cell_measurement_theta_min      2.31
_cell_volume                     4873.0(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'SHELXTL/XP, Bruker AXS, Inc. 2009'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT n/a (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            83413
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.642
_diffrn_reflns_theta_min         2.137
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    3.120
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5510
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0909 before and 0.0602 after correction.
The Ratio of minimum to maximum transmission is 0.7385.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_description       prism
_exptl_crystal_F_000             2248
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.09
_refine_diff_density_max         2.601
_refine_diff_density_min         -2.412
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     656
_refine_ls_number_reflns         14947
_refine_ls_number_restraints     456
_refine_ls_restrained_S_all      1.818
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0269P)^2^+6.2058P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11080
_reflns_number_total             14947
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc03339a2.cif
_cod_data_source_block           mebzau
_cod_depositor_comments
'Adding full bibliography for 7126638--7126640.cif.'
_cod_original_cell_volume        4872.8(17)
_cod_database_code               7126640
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.767
_shelx_estimated_absorpt_t_min   0.400
_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. Restrained distances
 C22-C13 = C13-C15A
 1.52 with sigma of 0.02
 C13-C15
 1.52 with sigma of 0.02
 C13-C14A
 1.52 with sigma of 0.02
 C13-C14
 1.52 with sigma of 0.02
 C44-C45 \\sim C44-C45A
 with sigma of 0.02
 C44-C49 \\sim C44-C49A
 with sigma of 0.02
 C45-C46 \\sim C45A-C46A
 with sigma of 0.02
 C46-C47 \\sim C46A-C47
 with sigma of 0.02
 C47-C48 \\sim C47-C48A
 with sigma of 0.02
 C48-C49 \\sim C48A-C49A
 with sigma of 0.02
 C44-C46 \\sim C44-C46A
 with sigma of 0.04
 C44-C48 \\sim C44-C48A
 with sigma of 0.04
 C45-C47 \\sim C45A-C47
 with sigma of 0.04
 C47-C49 \\sim C47-C49A
 with sigma of 0.04
 C13-C14 \\sim C13-C14A
 with sigma of 0.02
 C13-C15 \\sim C13-C15A
 with sigma of 0.02
 C14-C15 \\sim C14A-C15A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C15A \\sim C15 \\sim C14A \\sim C14: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
4. Others
 Sof(C45A)=Sof(H45A)=Sof(C46A)=Sof(H46A)=Sof(C48A)=Sof(H48A)=Sof(C49A)=
 Sof(H49A)=1-FVAR(1)
 Sof(C45)=Sof(H45)=Sof(C46)=Sof(H46)=Sof(C48)=Sof(H48)=Sof(C49)=Sof(H49)=FVAR(1)
 Sof(H13A)=Sof(C15A)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C14A)=Sof(H14D)=
 Sof(H14E)=Sof(H14F)=1-FVAR(2)
 Sof(H13)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=Sof(C15)=Sof(H15A)=Sof(H15B)=
 Sof(H15C)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C13(H13A), C22(H22), C25(H25)
5.b Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C41(H41A,H41B), C43(H43A,H43B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20),
 C29(H29), C30(H30), C33(H33), C35(H35), C45(H45), C46(H46), C48(H48), C49(H49),
  C45A(H45A), C46A(H46A), C48A(H48A), C49A(H49A)
5.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C),
 C50(H50A,H50B,H50C), C15A(H15D,H15E,H15F), C14A(H14D,H14E,H14F)
;
_shelx_res_checksum              7314
_olex2_submission_special_instructions 'No special instructions were received'