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_7126638
_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         'C60 H70 Au N6 O6, F6 P'
_chemical_formula_sum            'C60 H70 Au F6 N6 O6 P'
_chemical_formula_weight         1313.15
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-04-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-04-26 deposited with the CCDC.	2020-06-03 downloaded from the CCDC.
;
_cell_angle_alpha                102.209(4)
_cell_angle_beta                 97.728(4)
_cell_angle_gamma                104.498(5)
_cell_formula_units_Z            4
_cell_length_a                   10.8241(6)
_cell_length_b                   18.2147(9)
_cell_length_c                   32.3647(17)
_cell_measurement_reflns_used    2707
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.2
_cell_measurement_theta_min      1.65
_cell_volume                     5918.4(6)
_computing_cell_refinement       'ALS Beamline Operating Software, B3'
_computing_data_collection       'ALS Beamline Operating Software, B3'
_computing_data_reduction        'Rigaku OD, CrysAlisPro 1.171.40.46a'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.507
_diffrn_measured_fraction_theta_max 0.507
_diffrn_measurement_device_type  'ALS Beamline 5.0.1'
_diffrn_measurement_method       \p-scans
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.97741
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.507
_diffrn_reflns_Laue_measured_fraction_max 0.507
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6065
_diffrn_reflns_point_group_measured_fraction_full 0.507
_diffrn_reflns_point_group_measured_fraction_max 0.507
_diffrn_reflns_theta_full        26.257
_diffrn_reflns_theta_max         26.257
_diffrn_reflns_theta_min         2.067
_diffrn_source                   synchrotron
_exptl_absorpt_coefficient_mu    3.797
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.02
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       needle
_exptl_crystal_F_000             2672
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.224
_refine_diff_density_min         -2.429
_refine_diff_density_rms         0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.718
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1484
_refine_ls_number_reflns         4661
_refine_ls_number_restraints     1264
_refine_ls_restrained_S_all      2.151
_refine_ls_R_factor_all          0.1414
_refine_ls_R_factor_gt           0.1301
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3272
_refine_ls_wR_factor_ref         0.3380
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3729
_reflns_number_total             4661
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc03339a2.cif
_cod_data_source_block           au-morpholine
_cod_depositor_comments
'Adding full bibliography for 7126638--7126640.cif.'
_cod_database_code               7126638
_shelx_shelxl_version_number     2018/3
_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
 P1-F1 = P1-F2 = P1-F3 = P1-F4 = P1-F5 = P1-F6
 1.58 with sigma of 0.02
 P2-F7 = P2-F8 = P2-F9 = P2-F10 = P2-F11 = P2-F12
 1.58 with sigma of 0.02
 F1-F3 = F1-F4 = F1-F5 = F2-F3 = F2-F4 = F2-F5 = F2-F6 = F1-F6
 2.48 with sigma of 0.02
 F3-F4 = F3-F6 = F4-F6 = F5-F6 = F9_$1-F10_$1 = F9_$1-F11_$1 = F9_$1-F12_$1 =
 F10_$1-F11_$1 = F10_$1-F12_$1 = F11_$1-F12_$1
 2.48 with sigma of 0.02
 F7-F9 = F7-F10 = F7-F11 = F7-F12 = F8-F9 = F8-F10 = F8-F11 = F8-F12
 2.58 with sigma of 0.02
 C28-N3 = C28-N4 = C1-N2 = C1-N1 = C61-N7 = C61-N8 = C87-N9 = C87-N10
 1.35 with sigma of 0.02
 N4-C30 = N3-C29 = N1-C2 = N2-C3 = N7-C62 = N8-C63 = N9-C88 = N10-C89
 1.46 with sigma of 0.02
 C29-C30 = C2-C3 = C62-C63 = C88-C89
 1.34 with sigma of 0.02
 N3-C31 = N1-C4 = N2-C16 = N7-C64 = N8-C76 = N9-C90
 1.35 with sigma of 0.02
 C55-O5 = C45-O4
 1.22 with sigma of 0.02
 C45-C55
 2.48 with sigma of 0.02
 C54-C55 = C45-C46
 1.48 with sigma of 0.02
 C54-C56 = C46-C56
 1.41 with sigma of 0.02
 C49-N6
 1.4 with sigma of 0.02
 C50-C49
 1.4 with sigma of 0.02
 C50-C51
 1.4 with sigma of 0.02
 C109-C115
 1.45 with sigma of 0.02
 C109-C110
 1.4 with sigma of 0.02
 C109-C108
 1.4 with sigma of 0.02
 C108-C107
 1.4 with sigma of 0.02
 C104-C114
 2.48 with sigma of 0.02
 C114-C113
 1.47 with sigma of 0.02
 C113-C115
 1.41 with sigma of 0.02
 C115-C105
 1.41 with sigma of 0.02
 O11-C104
 1.22 with sigma of 0.02
 C114-O10
 1.22 with sigma of 0.02
 N11-O10
 2.27 with sigma of 0.02
 N11-O11
 2.27 with sigma of 0.02
 C109-C107
 2.42 with sigma of 0.02
 C109-C111
 2.42 with sigma of 0.02
 C113-C111
 2.42 with sigma of 0.02
 N12-C116
 1.48 with sigma of 0.02
 N12-C119
 1.48 with sigma of 0.02
 C116-C117
 1.5 with sigma of 0.02
 C119-C118
 1.5 with sigma of 0.02
 C118-O12
 1.42 with sigma of 0.02
 O12-C117
 1.42 with sigma of 0.02
 C119-C117
 2.8 with sigma of 0.02
 C118-C116
 2.8 with sigma of 0.02
 N12-O12
 2.8 with sigma of 0.02
 C118-C117
 2.32 with sigma of 0.02
 C119-C116
 2.4 with sigma of 0.02
 N11-C102
 2.4 with sigma of 0.03
 C103-C104
 2.4 with sigma of 0.03
 C103-C114
 2.4 with sigma of 0.03
 C103-O10
 2.6 with sigma of 0.05
 C103-O11
 2.6 with sigma of 0.05
 C103-C102
 1.45 with sigma of 0.04
 O9-C101
 1.3 with sigma of 0.03
 C101-O7
 1.3 with sigma of 0.03
 C101-O8
 1.2 with sigma of 0.03
 O9-O7
 2.3 with sigma of 0.03
 C111-C115
 2.8 with sigma of 0.02
 C105-C109
 2.4 with sigma of 0.02
 C115-C108
 2.4 with sigma of 0.02
 C105-C107
 2.4 with sigma of 0.02
 C106-C107
 1.38 with sigma of 0.02
 C112-C109
 2.8 with sigma of 0.02
 C109-C106
 2.8 with sigma of 0.02
 C113-C105
 2.4 with sigma of 0.02
 C105-C108
 2.8 with sigma of 0.02
 C108-C106
 2.4 with sigma of 0.02
 C110-C113
 2.8 with sigma of 0.02
 C115-C107
 2.8 with sigma of 0.02
 C61-C63
 2.15 with sigma of 0.02
 F9A-F12A
 2.36 with sigma of 0.02
 F10A-F11A
 2.36 with sigma of 0.02
 C87-C89
 2.2 with sigma of 0.02
 C102-C101
 2.4 with sigma of 0.03
 C103-O9
 2.4 with sigma of 0.02
 C102-C103
 1.45 with sigma of 0.02
 O9-C102
 1.3 with sigma of 0.02
 O9-C103
 2.25 with sigma of 0.02
 P2-F7 \\sim P2-F7A
 with sigma of 0.02
 P2-F11 \\sim P2-F11A
 with sigma of 0.02
 P2-F12 \\sim P2-F12A
 with sigma of 0.02
 P2-F8 \\sim P2-F8A
 with sigma of 0.02
 P2-F9 \\sim P2-F9A
 with sigma of 0.02
 P2-F10 \\sim P2-F10A
 with sigma of 0.02
 O7-O8 \\sim O8-O9
 with sigma of 0.01
3. Restrained planarity
 P2, F9, F10, F11, F12
 with sigma of 0.01
 O1, O2, O3, C42
 with sigma of 0.02
 O4, O5, N5, C45, C46, C47, C48, C49, C50, C51, C52, C53, C54, C55, C56
 with sigma of 0.02
 O10, O11, N11, C104, C105, C106, C107, C108, C109, C110, C111, C112, C113,
 C114, C115
 with sigma of 0.02
 O7, O8, O9, C101
 with sigma of 0.02
 N11, C104, C105, C106, C107, C108, C109, C115, C113, C114, O10, O11, C112,
 C111, C110
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
F10 \\sim F8A \\sim F8 \\sim F11A \\sim F9 \\sim F12A \\sim F7 \\sim F9A \\sim
F11 \\sim F10A \\sim F7A \\sim F12: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
F6 \\sim F3 \\sim F1 \\sim F4 \\sim F5 \\sim F2: 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
5. Others
 Sof(F7A)=Sof(F8A)=Sof(F9A)=Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(1)
 Sof(F7)=Sof(F8)=Sof(F9)=Sof(F10)=Sof(F11)=Sof(F12)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C70(H70), C73(H73), C82(H82), C85(H85), C10(H10), C13(H13), C22(H22), C25(H25)
6.b Secondary CH2 refined with riding coordinates:
 C99(H99A,H99B), C100(H10A,H10B), C102(H10C,H10D), C103(H10E,H10F), C116(H11D,
 H11E), C117(H11F,H11G), C118(H11H,H11I), C119(H11J,H11K), C40(H40A,H40B),
 C41(H41A,H41B), C43(H43A,H43B), C44(H44A,H44B), C57(H57A,H57B), C58(H58A,H58B),
  C59(H59A,H59B), C60(H60A,H60B)
6.c Me refined with riding coordinates:
 C11(H11A,H11B,H11C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C), C74(H74A,H74B,
 H74C), C75(H75A,H75B,H75C), C83(H83A,H83B,H83C), C84(H84A,H84B,H84C), C86(H86A,
 H86B,H86C), C96(H96A,H96B,H96C), C97(H97A,H97B,H97C), C98(H98A,H98B,H98C),
 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), C120(H12D,H12E,H12F)
6.d Aromatic/amide H refined with riding coordinates:
 C62(H62), C63(H63), C66(H66), C67(H67), C68(H68), C78(H78), C79(H79),
 C80(H80), C88(H88), C89(H89), C92(H92), C94(H94), C106(H106), C107(H107),
 C108(H108), C111(H111), C112(H112), C2(H2), C3(H3), C6(H6), C7(H7), C8(H8),
 C18(H18), C19(H19), C20(H20), C29(H29), C30(H30), C33(H33), C35(H35), C47(H47),
  C48(H48), C51(H51), C52(H52), C53(H53)
6.e Fitted hexagon refined as free rotating group:
 C109(C110,C111,C112,C113,C115)
;
_shelx_res_checksum              12436
_olex2_submission_special_instructions 'No special instructions were received'