Covalent and non-covalent albumin binding of Au(i) bis-NHCs <i>via</i> post-synthetic amide modification.
Sen, Sajal; Perrin, Mark W.; Sedgwick, Adam C.; Lynch, Vincent M.; Sessler, Jonathan L.; Arambula, Jonathan F.; Chemical science 12 (2021) 7547–7553; doi:10.1039/d1sc01055g

data_1562122
_publ_section_title
;
 Covalent and non-covalent albumin binding of Au(i) bis-NHCs <i>via</i>
 post-synthetic amide modification.
;
_journal_issue                   21
_journal_name_full               'Chemical science'
_journal_page_first              7547
_journal_page_last               7553
_journal_paper_doi               10.1039/d1sc01055g
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C27 H36 N2, C16 H21 N3 O2, Au 1+, P F6 1-''
_chemical_formula_sum            'C43 H57 Au F6 N5 O2 P'
_chemical_formula_weight         1017.87
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-01
_audit_creation_method
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_audit_update_record
;
2021-02-10 deposited with the CCDC.	2021-04-26 downloaded from the CCDC.
;
_cell_angle_alpha                101.6313(18)
_cell_angle_beta                 93.6495(19)
_cell_angle_gamma                101.640(2)
_cell_formula_units_Z            4
_cell_length_a                   11.0894(3)
_cell_length_b                   18.0488(4)
_cell_length_c                   24.6597(5)
_cell_measurement_reflns_used    13606
_cell_measurement_temperature    100.04(11)
_cell_measurement_theta_max      73.3150
_cell_measurement_theta_min      2.7610
_cell_volume                     4706.8(2)
_computing_cell_refinement       'CrysAlisPro 1.171.41.70a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.70a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.70a (Rigaku OD, 2020)'
_computing_molecular_graphics    'SHELXLTL-Plus/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_environment      N~2~
_diffrn_ambient_temperature      100.04(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2940
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -116.00 -17.00   0.50    5.50    --  -41.59 -38.00-120.00  198
  2  \w     34.00 133.00   0.50   20.50    --  107.09 -45.00  30.00  198
  3  \w    -66.00  33.00   0.50    5.50    --  -41.59  38.00  60.00  198
  4  \w    103.00 178.00   0.50   20.50    --  107.09  77.00-180.00  150
  5  \w    -74.00  35.00   0.50    5.50    --  -41.59  77.00 150.00  218
  6  \w     30.00 109.00   0.50   20.50    --  107.09-109.00-165.00  158
  7  \w      7.00  33.00   0.50    5.50    --   41.59  84.00-125.39   52
  8  \w     24.00 107.00   0.50   20.50    --  107.09 -94.00-150.00  166
  9  \w     34.00 133.00   0.50   20.50    --  107.09 -45.00-120.00  198
 10  \w    103.00 178.00   0.50   20.50    --  107.09  77.00 -30.00  150
 11  \w     24.00 107.00   0.50   20.50    --  107.09 -94.00 -90.00  166
 12  \w     24.00 107.00   0.50   20.50    --  107.09 -94.00  30.00  166
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1327516000
_diffrn_orient_matrix_UB_12      -0.0121261000
_diffrn_orient_matrix_UB_13      -0.0280675000
_diffrn_orient_matrix_UB_21      0.0512756000
_diffrn_orient_matrix_UB_22      0.0059063000
_diffrn_orient_matrix_UB_23      -0.0559695000
_diffrn_orient_matrix_UB_31      -0.0100233000
_diffrn_orient_matrix_UB_32      -0.0883135000
_diffrn_orient_matrix_UB_33      -0.0141553000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            32664
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.445
_diffrn_reflns_theta_min         2.808
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50826
_exptl_absorpt_correction_type   'gaussian and multi-scan'
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.70a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       needle
_exptl_crystal_F_000             2056
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.067
_refine_diff_density_max         1.953
_refine_diff_density_min         -1.452
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1208
_refine_ls_number_reflns         17996
_refine_ls_number_restraints     350
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0748P)^2^+1.8220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15115
_reflns_number_total             17996
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01055g2.cif
_cod_data_source_block           Complex3
_cod_depositor_comments
'Adding full bibliography for 1562121--1562124.cif.'
_cod_original_cell_volume        4706.79(19)
_cod_database_code               1562122
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C43H57N5O2PF6Au
_reflns_odcompleteness_completeness 90.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 P3-F13 = P3-F14 = P3-F15 = P3-F16 = P3-F17 = P3-F18
 1.58 with sigma of 0.02
 F13-F15 = F13-F16 = F13-F17 = F13-F18 = F14-F15 = F14-F16 = F14-F17 = F14-F18
 2.42 with sigma of 0.02
 F15-F16 = F15-F18 = F16-F17 = F17-F18
 2.42 with sigma of 0.02
 F7-F9 = F7-F10 = F7-F11 = F7-F12 = F8-F9 = F8-F10 = F8-F11 = F8-F12
 2.42 with sigma of 0.02
 P2-F7 = P2-F8 = P2-F9 = P2-F10 = P2-F11 = P2-F12
 1.57 with sigma of 0.02
 F9-F10 = F9-F12 = F10-F11 = F11-F12
 2.42 with sigma of 0.02
 C84-N10
 1.4 with sigma of 0.02
 C84A-N10A
 1.4 with sigma of 0.02
 C84A-C83
 1.5 with sigma of 0.02
 C84A-O3A
 1.22 with sigma of 0.02
 C84-O3
 1.22 with sigma of 0.02
 N10-C85
 1.45 with sigma of 0.02
 N10A-C85A
 1.45 with sigma of 0.02
 C85-C86A
 1.45 with sigma of 0.02
 N10-C86A
 2.4 with sigma of 0.02
 C85-O4
 2.4 with sigma of 0.02
 C86-O4
 1.4 with sigma of 0.02
 C86A-O4A
 1.4 with sigma of 0.02
 C86-C85
 1.48 with sigma of 0.02
 C86A-C85A
 1.48 with sigma of 0.02
 C60-C65 \\sim C60-C65A
 with sigma of 0.02
 C65-C66 \\sim C65A-C66A
 with sigma of 0.02
 C65-C67 \\sim C65A-C67A
 with sigma of 0.02
 C60-C66 \\sim C60-C66A
 with sigma of 0.04
 C60-C67 \\sim C60-C67A
 with sigma of 0.04
 C66-C67 \\sim C66A-C67A
 with sigma of 0.04
3. Restrained planarity
 C83, O3, N10, C84
 with sigma of 0.02
 C83, O3A, N10A, C84A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
F8 \\sim F15 \\sim F12 \\sim F10 \\sim F13 \\sim F17 \\sim F7 \\sim F9 \\sim
F11 \\sim F14 \\sim F16 \\sim F18: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
P2 \\sim P3: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
C66 \\sim C67A \\sim C67 \\sim C66A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
Uanis(P2) \\sim Ueq, Uanis(P3) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F8) \\sim
Ueq, Uanis(F9) \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F11) \\sim Ueq,
Uanis(F12) \\sim Ueq, Uanis(F13) \\sim Ueq, Uanis(F14) \\sim Ueq, Uanis(F15)
\\sim Ueq, Uanis(F16) \\sim Ueq, Uanis(F17) \\sim Ueq, Uanis(F18) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C84) \\sim Ueq, Uanis(C84A) \\sim Ueq, Uanis(N10) \\sim Ueq, Uanis(O3A)
\\sim Ueq, Uanis(O3) \\sim Ueq, Uanis(N10A) \\sim Ueq, Uanis(C85A) \\sim Ueq,
Uanis(C86A) \\sim Ueq, Uanis(O4A) \\sim Ueq, Uanis(C85) \\sim Ueq, Uanis(C86)
\\sim Ueq, Uanis(O4) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.02
Uanis(C65A) = Uanis(C65)
5. Rigid body (RIGU) restrains
 C84, C84A, N10, O3, O3A, C85, C86, O4, N10A, C85A, C86A, O4A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F15)=Sof(F13)=Sof(F17)=Sof(P3)=Sof(F14)=Sof(F16)=Sof(F18)=1-FVAR(1)
 Sof(F8)=Sof(F12)=Sof(P2)=Sof(F10)=Sof(F7)=Sof(F9)=Sof(F11)=FVAR(1)
 Sof(H83C)=Sof(H83D)=Sof(O3A)=Sof(O4A)=Sof(H4A)=Sof(N10A)=Sof(H10A)=Sof(C84A)=
 Sof(C85A)=Sof(H85C)=Sof(H85D)=Sof(C86A)=Sof(H86C)=Sof(H86D)=1-FVAR(2)
 Sof(H83A)=Sof(H83B)=Sof(O3)=Sof(O4)=Sof(H4)=Sof(N10)=Sof(H10)=Sof(C84)=
 Sof(C85)=Sof(H85A)=Sof(H85B)=Sof(C86)=Sof(H86A)=Sof(H86B)=FVAR(2)
 Sof(C67A)=Sof(H67D)=Sof(H67E)=Sof(H67F)=Sof(C65A)=Sof(H65A)=Sof(C66A)=
 Sof(H66D)=Sof(H66E)=Sof(H66F)=1-FVAR(3)
 Sof(C65)=Sof(H65)=Sof(C66)=Sof(H66A)=Sof(H66B)=Sof(H66C)=Sof(C67)=Sof(H67A)=
 Sof(H67B)=Sof(H67C)=FVAR(3)
7.a Ternary CH refined with riding coordinates:
 C53(H53), C56(H56), C65(H65), C68(H68), C10(H10B), C13(H13), C22(H22),
 C25(H25), C65A(H65A)
7.b Secondary CH2 refined with riding coordinates:
 C83(H83A,H83B), C83(H83C,H83D), C85(H85A,H85B), C86(H86A,H86B), C85A(H85C,
 H85D), C86A(H86C,H86D), C40(H40A,H40B), C42(H42A,H42B), C43(H43A,H43B)
7.c Me refined with riding coordinates:
 C66(H66A,H66B,H66C), C67(H67A,H67B,H67C), C67A(H67D,H67E,H67F), C66A(H66D,
 H66E,H66F)
7.d Aromatic/amide H refined with riding coordinates:
 C45(H45), C46(H46), C49(H49), C50(H50), C51(H51), C61(H61), C62(H62),
 C63(H63), C72(H72), C73(H73), C76(H76), C78(H78), N10(H10), N10A(H10A), N5(H5),
  C2(H2A), C3(H3), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20),
 C29(H29), C30(H30), C33(H33), C35(H35)
7.e Tetrahedral OH refined with riding coordinates:
 O4A(H4A)
7.f Idealised Me refined as rotating group:
 C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C57(H57A,H57B,H57C), C58(H58A,H58B,
 H58C), C69(H69A,H69B,H69C), C70(H70A,H70B,H70C), C80(H80A,H80B,H80C), C81(H81A,
 H81B,H81C), C82(H82A,H82B,H82C), 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)
7.g Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              22677
_shelx_hkl_checksum              27115
_shelx_fab_checksum              3073
_olex2_date_sample_data_collection 2020-06-29
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.688
_oxdiff_exptl_absorpt_empirical_full_min 0.571