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_1562124
_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         '2(C47 H58 Au N6 O3), 2(F6 P), C H2 Cl2'
_chemical_formula_sum            'C95 H118 Au2 Cl2 F12 N12 O6 P2'
_chemical_formula_weight         2278.78
_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             2020-07-21
_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                102.579(2)
_cell_angle_beta                 92.7990(10)
_cell_angle_gamma                98.3590(10)
_cell_formula_units_Z            2
_cell_length_a                   11.0621(2)
_cell_length_b                   18.0164(3)
_cell_length_c                   25.9531(5)
_cell_measurement_reflns_used    30088
_cell_measurement_temperature    100.04(11)
_cell_measurement_theta_max      73.1890
_cell_measurement_theta_min      2.7100
_cell_volume                     4977.26(16)
_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    '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)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.971
_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   1.00    4.00    --  -41.59 -38.00 150.00   99
  2  \w     31.00 135.00   1.00   16.00    --  107.09 -30.00  60.00  104
  3  \w    -66.00  33.00   1.00    4.00    --  -41.59  38.00 -30.00   99
  4  \w     81.00 178.00   1.00   16.00    --  107.09  45.00-120.00   97
  5  \w    -74.00  35.00   1.00    4.00    --  -41.59  77.00  60.00  109
  6  \w     24.00 107.00   1.00   16.00    --  107.09 -94.00  90.00   83
  7  \w      7.00  34.00   1.00    4.00    --   41.59  83.00 152.63   27
  8  \w     34.00 133.00   1.00   16.00    --  107.09 -45.00-120.00   99
  9  \w     26.00 160.00   1.00   16.00    --  107.09 -15.00-120.00  134
 10  \w     24.00 107.00   1.00   16.00    --  107.09 -94.00 -90.00   83
 11  \w     34.00 112.00   1.00   16.00    --  107.09-125.00  90.00   78
 12  \w     34.00 133.00   1.00   16.00    --  107.09 -45.00 150.00   99
 13  \w     26.00 107.00   1.00   16.00    --  107.09 -99.00-174.50   81
 14  \w   -115.00 -13.00   1.00    4.00    --  -41.59 -57.00 -30.00  102
 15  \w      9.00  42.00   1.00    4.00    --   41.59  77.00  90.44   33
 16  \w      7.00  33.00   1.00    4.00    --   41.59  84.00 -62.75   26
 17  \w     54.00 178.00   1.00   16.00    --  107.09  15.00 150.00  124
 18  \w     79.00 178.00   1.00   16.00    --  107.09  30.00 -30.00   99
 19  \w     78.00 178.00   1.00   16.00    --  107.09  61.00-180.00  100
 20  \w     81.00 178.00   1.00   16.00    --  107.09  45.00   0.00   97
 21  \w     78.00 178.00   1.00   16.00    --  107.09  61.00 -90.00  100
 22  \w     79.00 178.00   1.00   16.00    --  107.09  30.00  60.00   99
 23  \w    -87.00  -6.00   1.00    4.00    --  -41.59 125.00 120.00   81
 24  \w      7.00  34.00   1.00    4.00    --   41.59  83.00 -22.99   27
 25  \w      7.00  33.00   1.00    4.00    --   41.59  84.00 -89.90   26
 26  \w     78.00 153.00   1.00   16.00    --  107.09  61.00 150.00   75
;
_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      -0.1410227000
_diffrn_orient_matrix_UB_12      -0.0158084000
_diffrn_orient_matrix_UB_13      -0.0021253000
_diffrn_orient_matrix_UB_21      0.0078778000
_diffrn_orient_matrix_UB_22      -0.0098331000
_diffrn_orient_matrix_UB_23      0.0575057000
_diffrn_orient_matrix_UB_31      -0.0016753000
_diffrn_orient_matrix_UB_32      0.0867817000
_diffrn_orient_matrix_UB_33      0.0203339000
_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  0.0350
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            66015
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.389
_diffrn_reflns_theta_min         2.742
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.933
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.307
_exptl_absorpt_correction_type   'gaussian and multi-scan'
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.70a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.521
_exptl_crystal_description       plank
_exptl_crystal_F_000             2300
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.046
_refine_diff_density_max         1.105
_refine_diff_density_min         -1.538
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1467
_refine_ls_number_reflns         19449
_refine_ls_number_restraints     1779
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+14.9740P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0940
_reflns_Friedel_coverage         0.000
_reflns_number_gt                17241
_reflns_number_total             19449
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01055g2.cif
_cod_data_source_block           Complex7
_cod_depositor_comments
'Adding full bibliography for 1562121--1562124.cif.'
_cod_database_code               1562124
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C95H118Au2Cl2P2F12N12O6
_reflns_odcompleteness_completeness 99.50
_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
2. Restrained distances
 P2A-F7A = P2A-F8A = P2A-F9A = P2A-F10A = P2A-F11A = P2A-F12A
 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
 C44-O2 = C47-O3 = C44A-O2A = C47A-O3A
 1.21 with sigma of 0.02
 N6-C44 = N6-C47 = N6A-C44A = N6A-C47A
 1.39 with sigma of 0.02
 C44-C45 = C46-C47 = C44A-C45A = C46A-C47A
 1.49 with sigma of 0.02
 C45-C46 = C45A-C46A
 1.33 with sigma of 0.02
 N6-C43 = N6A-C43A
 1.45 with sigma of 0.02
 C43-C44 = C43-C47 = C43A-C44A = C43A-C47A
 2.52 with sigma of 0.02
 C44-C47 = C44A-C47A = C44-C46 = C44A-C46A = C45-C47 = C45A-C47A
 2.29 with sigma of 0.02
 N6-O2 = N6-O3 = N6A-O2A = N6A-O3A
 2.29 with sigma of 0.02
 Cl1-C1A = Cl2-C1A = Cl1A-C1B = Cl2A-C1B
 1.75 with sigma of 0.02
 O4A-C88A
 1.2 with sigma of 0.02
 N11A-C88A
 1.33 with sigma of 0.02
 C88A-C87A
 1.5 with sigma of 0.02
 C89-N11
 1.35 with sigma of 0.02
 C89A-N11A
 1.35 with sigma of 0.02
 C90A-C89A
 1.52 with sigma of 0.02
 F7A-F9A \\sim F7A-F10A \\sim F7A-F11A \\sim F7A-F12A \\sim F8A-F9A \\sim
F8A-F10A \\sim F8A-F11A ~
 F8A-F12A
 with sigma of 0.01
 F9A-F10A \\sim F9A-F12A \\sim F10A-F11A \\sim F11A-F12A
 with sigma of 0.01
 F8-F9 \\sim F7-F10 \\sim F7-F11 \\sim F7-F12 \\sim F8-F9 \\sim F8-F10 \\sim
F8-F11 \\sim F8-F12
 with sigma of 0.01
 F9-F10 \\sim F9-F12 \\sim F10-F11 \\sim F11-F12
 with sigma of 0.01
 N6-C43 \\sim N6A-C43A
 with sigma of 0.02
 N6-C47 \\sim N6A-C47A
 with sigma of 0.02
 N6-C44 \\sim N6A-C44A
 with sigma of 0.02
 O3-C47 \\sim O3A-C47A
 with sigma of 0.02
 O2-C44 \\sim O2A-C44A
 with sigma of 0.02
 C42-C43 \\sim C42-C43A
 with sigma of 0.02
 C47-C46 \\sim C47A-C46A
 with sigma of 0.02
 C44-C45 \\sim C44A-C45A
 with sigma of 0.02
 C46-C45 \\sim C46A-C45A
 with sigma of 0.02
 N6-O3 \\sim N6A-O3A
 with sigma of 0.04
 N6-O2 \\sim N6A-O2A
 with sigma of 0.04
 N6-C42 \\sim N6A-C42
 with sigma of 0.04
 N6-C46 \\sim N6A-C46A
 with sigma of 0.04
 N6-C45 \\sim N6A-C45A
 with sigma of 0.04
 O3-C46 \\sim O3A-C46A
 with sigma of 0.04
 O2-C45 \\sim O2A-C45A
 with sigma of 0.04
 C43-C47 \\sim C43A-C47A
 with sigma of 0.04
 C43-C44 \\sim C43A-C44A
 with sigma of 0.04
 C47-C44 \\sim C47A-C44A
 with sigma of 0.04
 C47-C45 \\sim C47A-C45A
 with sigma of 0.04
 C44-C46 \\sim C44A-C46A
 with sigma of 0.04
 Cl2-C1A \\sim Cl2A-C1B
 with sigma of 0.02
 Cl1-C1A \\sim Cl1A-C1B
 with sigma of 0.02
 Cl2-Cl1 \\sim Cl2A-Cl1A
 with sigma of 0.04
 Cl1-Cl2 \\sim Cl1A-Cl2A
 with sigma of 0.01
 C91-O5 \\sim C91A-O5A
 with sigma of 0.02
 C91-N12 \\sim C91A-N12A
 with sigma of 0.02
 C91-C92 \\sim C91A-C92A
 with sigma of 0.02
 N12-C94 \\sim N12A-C94A
 with sigma of 0.02
 N12-C90 \\sim N12A-C90A
 with sigma of 0.02
 O6-C94 \\sim O6A-C94A
 with sigma of 0.02
 C89-C90 \\sim C89-C90A
 with sigma of 0.02
 C92-C93 \\sim C92A-C93A
 with sigma of 0.02
 C94-C93 \\sim C94A-C93A
 with sigma of 0.02
 C91-C94 \\sim C91A-C94A
 with sigma of 0.04
 C91-C93 \\sim C91A-C93A
 with sigma of 0.04
 C91-C90 \\sim C91A-C90A
 with sigma of 0.04
 O5-N12 \\sim O5A-N12A
 with sigma of 0.04
 O5-C92 \\sim O5A-C92A
 with sigma of 0.04
 N12-O6 \\sim N12A-O6A
 with sigma of 0.04
 N12-C89 \\sim N12A-C89
 with sigma of 0.04
 N12-C92 \\sim N12A-C92A
 with sigma of 0.04
 N12-C93 \\sim N12A-C93A
 with sigma of 0.04
 O6-C93 \\sim O6A-C93A
 with sigma of 0.04
 C92-C94 \\sim C92A-C94A
 with sigma of 0.04
 C94-C90 \\sim C94A-C90A
 with sigma of 0.04
3. Restrained planarity
 C43, N6, C44, O2, C45, C46, C47, O3
 with sigma of 0.01
 C43A, N6A, C44A, O2A, C45A, C46A, C47A, O3A
 with sigma of 0.01
 O6, C94, C93, C92, C91, N12, O5
 with sigma of 0.01
 C90A, N12A, C94A, O6A, C93A, C92A, O5A, C91A
 with sigma of 0.01
 O6A, C94A, C93A, C92A, C91A, N12A, C90A, O5A
 with sigma of 0.02
 C87A, C88A, O4A, N11A
 with sigma of 0.02
 C87, C88, N11, O4
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
F9 \\sim F7 \\sim F12 \\sim F10 \\sim F8 \\sim F11 \\sim F11A \\sim F12A \\sim
F10A \\sim F7A \\sim F9A \\sim F8A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
P2 \\sim P2A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
within 2A
C43A \\sim C43 \\sim N6A \\sim N6 \\sim C47A \\sim C47 \\sim O3 \\sim O3A \\sim
C46A \\sim C46 \\sim C45A \\sim C45 \\sim C44A \\sim C44 \\sim O2 \\sim O2A:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C1A \\sim C1B \\sim Cl2 \\sim Cl2A \\sim Cl1A \\sim Cl1: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
C90A \\sim C90 \\sim N12 \\sim N12A \\sim O6 \\sim O6A \\sim C94A \\sim C94
\\sim C93 \\sim C93A \\sim C92 \\sim C92A \\sim C91A \\sim O5A \\sim O5 \\sim
C91: 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
Uanis(Cl2A) = Uanis(Cl2) = Uanis(Cl1A) = Uanis(Cl1)
5. Others
 Sof(C90A)=Sof(H90C)=Sof(H90D)=Sof(N12A)=Sof(C91A)=Sof(C94A)=Sof(C93A)=
 Sof(H93A)=Sof(C92A)=Sof(H92A)=Sof(O6A)=Sof(O5A)=Sof(O4A)=Sof(C88A)=Sof(C87A)=
 Sof(H87C)=Sof(H87D)=Sof(C89A)=Sof(H89C)=Sof(H89D)=Sof(N11A)=Sof(H11A)=1-FVAR(1)
 Sof(C91)=Sof(N11)=Sof(H11)=Sof(O4)=Sof(O5)=Sof(C87)=Sof(H87A)=Sof(H87B)=
 Sof(N12)=Sof(C88)=Sof(O6)=Sof(C89)=Sof(H89A)=Sof(H89B)=Sof(C92)=Sof(H92)=
 Sof(C94)=Sof(C93)=Sof(H93)=Sof(C90)=Sof(H90A)=Sof(H90B)=FVAR(1)
 Sof(P2A)=Sof(F11A)=Sof(F12A)=Sof(F10A)=Sof(F7A)=Sof(F9A)=Sof(F8A)=1-FVAR(2)
 Sof(P2)=Sof(F9)=Sof(F7)=Sof(F12)=Sof(F10)=Sof(F8)=Sof(F11)=FVAR(2)
 Sof(H42C)=Sof(H42D)=Sof(O3A)=Sof(C47A)=Sof(C46A)=Sof(H46A)=Sof(C45A)=
 Sof(H45A)=Sof(C44A)=Sof(O2A)=Sof(N6A)=Sof(C43A)=Sof(H43C)=Sof(H43D)=1-FVAR(3)
 Sof(N6)=Sof(O3)=Sof(O2)=Sof(H42A)=Sof(H42B)=Sof(C43)=Sof(H43A)=Sof(H43B)=
 Sof(C47)=Sof(C44)=Sof(C46)=Sof(H46)=Sof(C45)=Sof(H45)=FVAR(3)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=1-FVAR(4)
 Sof(Cl2)=Sof(Cl1)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=FVAR(4)
6.a Ternary CH refined with riding coordinates:
 C60(H60), C25(H25), C10(H10), C72(H72), C57(H57), C13(H13), C69(H69), C22(H22)
6.b Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C87(H87A,H87B), C42(H42A,H42B), C42(H42C,H42D), C43(H43A,
 H43B), C89(H89A,H89B), C90(H90A,H90B), C1A(H1AA,H1AB), C90A(H90C,H90D),
 C43A(H43C,H43D), C1B(H1BA,H1BB), C87A(H87C,H87D), C89A(H89C,H89D)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C54(H54), C7(H7), C55(H55), C3(H3), C50(H50), C53(H53), C49(H49),
 C35(H35), C20(H20), C6(H6), C82(H82), C19(H19), C18(H18), N5(H5), C8(H8),
 C33(H33), C76(H76), C67(H67), C80(H80), N11(H11), C77(H77), C29(H29), C30(H30),
  C66(H66), C65(H65), C92(H92), C46(H46), C93(H93), C45(H45), C93A(H93A),
 C92A(H92A), C46A(H46A), C45A(H45A), N11A(H11A)
6.d Idealised Me refined as rotating group:
 C74(H74A,H74B,H74C), C86(H86A,H86B,H86C), C11(H11B,H11C,H11D), C38(H38A,H38B,
 H38C), C84(H84A,H84B,H84C), C37(H37A,H37B,H37C), C39(H39A,H39B,H39C), C58(H58A,
 H58B,H58C), C70(H70A,H70B,H70C), C85(H85A,H85B,H85C), C62(H62A,H62B,H62C),
 C15(H15A,H15B,H15C), C59(H59A,H59B,H59C), C14(H14A,H14B,H14C), C24(H24A,H24B,
 H24C), C12(H12A,H12B,H12C), C23(H23A,H23B,H23C), C61(H61A,H61B,H61C), C73(H73A,
 H73B,H73C), C27(H27A,H27B,H27C), C26(H26A,H26B,H26C), C71(H71A,H71B,H71C)
;
_shelx_res_checksum              83081
_shelx_hkl_checksum              64559
_olex2_date_sample_data_collection 2020-07-14
_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 1.692
_oxdiff_exptl_absorpt_empirical_full_min 0.724