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_1562123
_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, C18 H23 N3 O2, Au 1+, P F6 1-'
_chemical_formula_sum            'C45 H59 Au F6 N5 O2 P'
_chemical_formula_weight         1043.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-24
_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                90
_cell_angle_beta                 100.564(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.3001(3)
_cell_length_b                   50.4909(13)
_cell_length_c                   17.6766(4)
_cell_measurement_reflns_used    12634
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.5390
_cell_measurement_theta_min      3.5140
_cell_volume                     9914.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.67a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.67a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.67a (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      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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    -42.00  13.00   0.50    8.00    --  -47.95  37.00  90.00  110
  2  \w    -29.00  28.00   0.50    8.00    --  -47.95  19.00 -30.00  114
  3  \w    -34.00  22.00   0.50    8.00    --  -47.95  37.00  30.00  112
  4  \w    -20.00  24.00   0.50    8.00    --   47.95 -19.00 -90.00   88
  5  \w      7.00  46.00   0.50    8.00    --   47.95 -99.00-150.00   78
  6  \w    -63.00 -37.00   0.50   32.00    --  -91.75  57.00-180.00   52
  7  \w    -84.00 -20.00   0.50   32.00    --  -91.75 125.00 -90.00  128
  8  \w    -68.00 -26.00   0.50   32.00    --  -91.75 125.00-150.00   84
  9  \w   -131.00-103.00   0.50   32.00    --  -91.75 -57.00 -30.00   56
 10  \w     38.00  65.00   0.50   32.00    --  107.11 -57.00-120.00   54
 11  \w     72.00 103.00   0.50   32.00    --  107.11 -99.00  90.00   62
 12  \w    102.00 162.00   0.50   32.00    --  107.11  57.00  90.00  120
 13  \w     35.00  93.00   0.50   32.00    --  107.11 -77.00   0.00  116
 14  \w     71.00  97.00   0.50   32.00    --  107.11 -99.00   0.00   52
 15  \w     40.00  66.00   0.50   32.00    --  107.11 -57.00-150.00   52
 16  \w     49.00  96.00   0.50   32.00    --  107.11 -77.00  30.00   94
 17  \w    113.00 155.00   0.50   32.00    --  107.11  37.00  60.00   84
 18  \w     36.00 110.00   0.50   32.00    --  107.11-125.00-180.00  148
 19  \w     88.00 168.00   0.50   32.00    --  107.11  77.00  60.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0018401000
_diffrn_orient_matrix_UB_12      -0.0174691000
_diffrn_orient_matrix_UB_13      0.0715265000
_diffrn_orient_matrix_UB_21      0.0304122000
_diffrn_orient_matrix_UB_22      -0.0243533000
_diffrn_orient_matrix_UB_23      -0.0454947000
_diffrn_orient_matrix_UB_31      0.1353826000
_diffrn_orient_matrix_UB_32      0.0056943000
_diffrn_orient_matrix_UB_33      0.0258912000
_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  0.0781
_diffrn_reflns_av_unetI/netI     0.1061
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       60
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            56285
_diffrn_reflns_point_group_measured_fraction_full 0.797
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         2.543
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.401
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72943
_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    1.399
_exptl_crystal_description       needle
_exptl_crystal_F_000             4224
_exptl_crystal_size_max          0.093
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.643
_refine_diff_density_min         -1.715
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.465(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2345
_refine_ls_number_reflns         28213
_refine_ls_number_restraints     4029
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0615
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0605P)^2^+14.3210P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1375
_refine_ls_wR_factor_ref         0.1499
_reflns_Friedel_coverage         0.591
_reflns_Friedel_fraction_full    0.600
_reflns_Friedel_fraction_max     0.600
_reflns_number_gt                20082
_reflns_number_total             28213
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc01055g2.cif
_cod_data_source_block           Complex4
_cod_depositor_comments
'Adding full bibliography for 1562121--1562124.cif.'
_cod_database_code               1562123
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'Au N5 O2 C45 H62 P F6'
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.587
_reflns_odcompleteness_completeness 99.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.535(13)
 0.465(13)
2. 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
3. Restrained distances
 P4-F19 = P4-F20 = P4-F21 = P4-F22 = P4-F23 = P4-F24
 1.58 with sigma of 0.02
 F19-F21 = F19-F22 = F19-F23 = F19-F24
 2.33 with sigma of 0.02
 F20-F21 = F20-F22 = F20-F23 = F20-F24 = F21-F22 = F21-F24 = F22-F23 = F23-F24
 2.33 with sigma of 0.02
 C68-C62
 2.5 with sigma of 0.02
 C69-C62
 2.5 with sigma of 0.02
 C67-C68 = C67-C69
 1.5 with sigma of 0.02
 C231-C230
 1.5 with sigma of 0.02
 C130-C131
 1.5 with sigma of 0.02
 C231-O5A
 1.2 with sigma of 0.02
 O5-C131
 1.2 with sigma of 0.02
 N15A-C231
 1.35 with sigma of 0.02
 N15-C131
 1.35 with sigma of 0.02
 C235-N15A
 1.47 with sigma of 0.02
 C232-N15A
 1.47 with sigma of 0.02
 N15-C132
 1.47 with sigma of 0.02
 C135-N15
 1.47 with sigma of 0.02
 C234-C235
 1.49 with sigma of 0.02
 C135-C134
 1.49 with sigma of 0.02
 C133-C132
 1.49 with sigma of 0.02
 C232-C233
 1.49 with sigma of 0.02
 O6-C133
 1.42 with sigma of 0.02
 O6-C134
 1.42 with sigma of 0.02
 C234-O6A
 1.42 with sigma of 0.02
 O6A-C233
 1.42 with sigma of 0.02
 C134-C133
 2.33 with sigma of 0.02
 C233-C234
 2.33 with sigma of 0.02
 C232-C235
 2.44 with sigma of 0.02
 C132-C135
 2.44 with sigma of 0.02
 N15-O6
 2.8 with sigma of 0.02
 N15A-O6A
 2.8 with sigma of 0.02
 C133-C135
 2.8 with sigma of 0.02
 C233-C235
 2.8 with sigma of 0.02
 C132-C134
 2.8 with sigma of 0.02
 C234-C232
 2.8 with sigma of 0.02
 C231-C235
 2.47 with sigma of 0.02
 C232-C231
 2.47 with sigma of 0.02
 C131-C132
 2.47 with sigma of 0.02
 C131-C135
 2.47 with sigma of 0.02
 P4-F19 \\sim P4A-F23A
 with sigma of 0.02
 P4-F21 \\sim P4A-F24A
 with sigma of 0.02
 P4-F23 \\sim P4A-F19A
 with sigma of 0.02
 P4-F24 \\sim P4A-F21A
 with sigma of 0.02
 P4-F19 \\sim P4A-F19A
 with sigma of 0.02
 P4-F20 \\sim P4A-F20A
 with sigma of 0.02
 P4-F21 \\sim P4A-F21A
 with sigma of 0.02
 P4-F22 \\sim P4A-F22A
 with sigma of 0.02
 P4-F23 \\sim P4A-F23A
 with sigma of 0.02
 P4-F24 \\sim P4A-F24A
 with sigma of 0.02
 O5-C131 \\sim O5A-C231
 with sigma of 0.02
 O6-C133 \\sim O6A-C233
 with sigma of 0.02
 O6-C134 \\sim O6A-C234
 with sigma of 0.02
 N14-C130 \\sim N14-C230
 with sigma of 0.02
 N15-C131 \\sim N15A-C231
 with sigma of 0.02
 N15-C132 \\sim N15A-C232
 with sigma of 0.02
 N15-C135 \\sim N15A-C235
 with sigma of 0.02
 C130-C131 \\sim C230-C231
 with sigma of 0.02
 C132-C133 \\sim C232-C233
 with sigma of 0.02
 C134-C135 \\sim C234-C235
 with sigma of 0.02
 O5-N15 \\sim O5A-N15A
 with sigma of 0.04
 O5-C130 \\sim O5A-C230
 with sigma of 0.04
 O6-C132 \\sim O6A-C232
 with sigma of 0.04
 O6-C135 \\sim O6A-C235
 with sigma of 0.04
 N14-C131 \\sim N14-C231
 with sigma of 0.04
 N15-C130 \\sim N15A-C230
 with sigma of 0.04
 N15-C133 \\sim N15A-C233
 with sigma of 0.04
 N15-C134 \\sim N15A-C234
 with sigma of 0.04
 C131-C132 \\sim C231-C232
 with sigma of 0.04
 C131-C135 \\sim C231-C235
 with sigma of 0.04
 C132-C135 \\sim C232-C235
 with sigma of 0.04
 C133-C134 \\sim C233-C234
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
F19 \\sim F20 \\sim F21 \\sim F22 \\sim F23 \\sim F24 \\sim F19A \\sim F20A
\\sim F21A \\sim F22A \\sim F23A \\sim F24A: within 2A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 2A
O5A \\sim C231 \\sim C230 \\sim C130 \\sim C131 \\sim O5 \\sim N15A \\sim N15
\\sim C235 \\sim C135 \\sim C134 \\sim C234 \\sim O6 \\sim O6A \\sim C233 \\sim
C133 \\sim C132 \\sim C232: 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(P4) = Uanis(P4A)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(P4A)=Sof(F19A)=Sof(F20A)=Sof(F21A)=Sof(F22A)=Sof(F23A)=Sof(F24A)=1-FVAR(1)
 Sof(P4)=Sof(F19)=Sof(F20)=Sof(F21)=Sof(F22)=Sof(F23)=Sof(F24)=FVAR(1)
 Sof(C230)=Sof(H23A)=Sof(H23B)=Sof(C231)=Sof(O5A)=Sof(N15A)=Sof(C232)=
 Sof(H23C)=Sof(H23D)=Sof(C233)=Sof(H23E)=Sof(H23F)=Sof(C235)=Sof(H23G)=
 Sof(H23H)=Sof(C234)=Sof(H23I)=Sof(H23J)=Sof(O6A)=1-FVAR(2)
 Sof(O5)=Sof(O6)=Sof(N15)=Sof(C130)=Sof(H13A)=Sof(H13B)=Sof(C131)=Sof(C132)=
 Sof(H13C)=Sof(H13D)=Sof(C133)=Sof(H13E)=Sof(H13F)=Sof(C134)=Sof(H13G)=
 Sof(H13H)=Sof(C135)=Sof(H13I)=Sof(H13J)=FVAR(2)
 Fixed Y: Au1(0.490749)
7.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25), C100(H100), C103(H103), C112(H112),
 C115(H115), C55(H55), C58(H58), C67(H67), C70(H70), C145(H145), C148(H148),
 C157(H157), C160(H160)
7.b Secondary CH2 refined with riding coordinates:
 C40(H40A,H40B), C42(H42A,H42B), C43(H43A,H43B), C44(H44A,H44B), C45(H45A,
 H45B), C130(H13A,H13B), C132(H13C,H13D), C133(H13E,H13F), C134(H13G,H13H),
 C135(H13I,H13J), C85(H85A,H85B), C87(H87A,H87B), C88(H88A,H88B), C89(H89A,
 H89B), C90(H90A,H90B), C175(H17J,H17K), C177(H17L,H17M), C178(H17N,H17O),
 C179(H17P,H17Q), C180(H18A,H18B), C230(H23A,H23B), C232(H23C,H23D), C233(H23E,
 H23F), C235(H23G,H23H), C234(H23I,H23J)
7.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), C92(H92), C93(H93), C96(H96), C97(H97),
  C98(H98), C108(H108), C109(H109), C110(H110), C119(H119), C120(H120),
 C123(H123), C125(H125), C47(H47), C48(H48), C51(H51), C52(H52), C53(H53),
 C63(H63), C64(H64), C65(H65), C74(H74), C75(H75), C78(H78), C80(H80),
 C137(H137), C138(H138), C141(H141), C142(H142), C143(H143), C153(H153),
 C154(H154), C155(H155), C164(H164), C165(H165), C168(H168), C170(H170)
7.d Idealised Me refined as rotating group:
 C11(H11M,H11N,H11O), C12(H12J,H12K,H12L), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23K,H23L,H23M), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C),
 C101(H10A,H10B,H10C), C102(H10D,H10E,H10F), C104(H10G,H10H,H10I), C105(H10J,
 H10K,H10L), C113(H11A,H11B,H11C), C114(H11D,H11E,H11F), C116(H11G,H11H,H11I),
 C117(H11J,H11K,H11L), C127(H12A,H12B,H12C), C128(H12D,H12E,H12F), C129(H12G,
 H12H,H12I), C56(H56A,H56B,H56C), C57(H57A,H57B,H57C), C59(H59A,H59B,H59C),
 C60(H60A,H60B,H60C), C71(H71A,H71B,H71C), C72(H72A,H72B,H72C), C82(H82A,H82B,
 H82C), C83(H83A,H83B,H83C), C84(H84A,H84B,H84C), C146(H14D,H14E,H14F),
 C147(H14G,H14H,H14I), C149(H14J,H14K,H14L), C150(H15D,H15E,H15F), C158(H15G,
 H15H,H15I), C159(H15J,H15K,H15L), C161(H16A,H16B,H16C), C162(H16D,H16E,H16F),
 C172(H17A,H17B,H17C), C173(H17D,H17E,H17F), C174(H17G,H17H,H17I), C68(H68A,
 H68B,H68C), C69(H69A,H69B,H69C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              52342
_shelx_hkl_checksum              80399
_shelx_fab_checksum              74935
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   2097
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.474
_oxdiff_exptl_absorpt_empirical_full_min 0.560