Phosphinoamine coinage metal complexes with a coumarin fluorophore: synthesis, characterization, and <i>in vitro</i> (photo)cytotoxicity.
Naina, Vanitha R.; Shubham, ?; Rönicke, Franziska; Wagenknecht, Hans-Achim; Roesky, Peter W.; Dalton transactions (Cambridge, England : 2003) 54 (2025) 14701–14709; doi:10.1039/d5dt01532d

data_7719467
_publ_section_title
;
 Phosphinoamine coinage metal complexes with a coumarin fluorophore:
 synthesis, characterization, and <i>in vitro</i> (photo)cytotoxicity.
;
_journal_issue                   39
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14701
_journal_page_last               14709
_journal_paper_doi               10.1039/d5dt01532d
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety
'C60 H68 Au N2 O4 P2, 1(F6 Sb1), 2[C4H8O], 1[C4H8O]'
_chemical_formula_sum            'C72 H92 Au F6 N2 O7 P2 Sb'
_chemical_formula_weight         1592.13
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-1
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_audit_update_record
;
2025-06-25 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.316(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.6767(4)
_cell_length_b                   15.3577(4)
_cell_length_c                   28.0869(11)
_cell_measurement_reflns_used    43630
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.02
_cell_measurement_theta_min      1.96
_cell_volume                     3742.6(2)
_computing_cell_refinement
;
X-Area Recipe 1.37.0.0 (STOE, 2021)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.186.0 (STOE, 2022)
;
_computing_data_reduction
;
X-Area Integrate 2.5.3.0 (STOE, 2021)
X-Area LANA 2.7.5.0 (STOE, 2022)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'EIGER2 1M CDTE'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
 564 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            39804
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_min         1.965
_diffrn_source                   Axo_Mo
_diffrn_source_current           0.830
_diffrn_source_power             0.050
_diffrn_source_voltage           60
_exptl_absorpt_coefficient_mu    2.426
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  1.0000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.026
_refine_diff_density_max         1.099
_refine_diff_density_min         -0.928
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         6784
_refine_ls_number_restraints     1023
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0476
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+10.0386P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4825
_reflns_number_total             6784
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt01532d2.cif
_cod_data_source_block           nv324
_cod_depositor_comments
'Adding full bibliography for 7719466--7719467.cif.'
_cod_database_code               7719467
_shelx_shelxl_version_number     2018/3
_audit_contact_author
;
      Prof. Dr. Peter W. Roesky
      Karlsruher Institut fuer Technologie (KIT), CS
      Institut fuer Anorganische Chemie (AOC)
      Lehrstuhl fuer Anorganische Funktionsmaterialien
      Engesserstr. 15, Geb. 30.45
      76131 Karlsruhe 
      Bundesrepublik Deutschland
;
_audit_contact_letter
;
;
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.746
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 SbB-F2B = SbB-F1B
 1.87 with sigma of 0.02
 SbA-F2A = SbA-F1A
 1.87 with sigma of 0.02
 SbB-F6B = SbB-F3B = SbB-F5B = SbB-F4B
 1.88 with sigma of 0.02
 SbA-F3A = SbA-F4A = SbA-F6A = SbA-F5A
 1.88 with sigma of 0.02
 C24A-C30A \\sim C24B-C28B
 with sigma of 0.04
 P-C21A \\sim P-C21B
 with sigma of 0.02
 F3A-F4A \\sim F3A-F2A \\sim F3A-F6A \\sim F3A-F1A \\sim F4A-F2A \\sim F4A-F1A
\\sim F4A-F5A \\sim F2A-F6A
 \\sim F2A-F5A \\sim F6A-F1A \\sim F6A-F5A \\sim F1A-F5A
 with sigma of 0.04
 F6B-F3B \\sim F6B-F2B \\sim F6B-F5B \\sim F6B-F1B \\sim F3B-F2B \\sim F3B-F1B
\\sim F3B-F4B \\sim F2B-F5B
 \\sim F2B-F4B \\sim F5B-F1B \\sim F5B-F4B \\sim F1B-F4B
 with sigma of 0.04
 C14A-C13A \\sim C14B-C13B
 with sigma of 0.02
3. Rigid bond restraints
 C13, C11, C14, C15, C16, C17, C18
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C13 \\sim C11 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18: within 2.5A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2.5A
SbA \\sim F3A \\sim F4A \\sim F2A \\sim F6A \\sim F1A \\sim F5A \\sim SbB \\sim
F6B \\sim F3B \\sim F2B \\sim F5B \\sim F1B \\sim F4B: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
SbA \\sim F3A \\sim F4A \\sim F2A \\sim F6A \\sim F1A \\sim F5A: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
SbB \\sim F6B \\sim F3B \\sim F2B \\sim F5B \\sim F1B \\sim F4B: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C21A \\sim C21B \\sim C22B \\sim C22A \\sim C23B \\sim C23A \\sim C24A \\sim
C24B \\sim C25B \\sim C25A \\sim C26A \\sim C26B \\sim C27A \\sim C27B \\sim
C29A \\sim C30B \\sim C28B \\sim C28A \\sim C30A \\sim C29B: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C11A \\sim C14A \\sim C13A \\sim C16A \\sim C12A \\sim C15A \\sim C13B \\sim
C12B \\sim C11B \\sim C16B \\sim C15B \\sim C14B: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 2A
Uanis(C28A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 SbB, F6B, F3B, F2B, F5B, F1B, F4B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 SbA, F3A, F4A, F2A, F6A, F1A, F5A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(SbB)=Sof(F6B)=Sof(F3B)=Sof(F2B)=Sof(F5B)=Sof(F1B)=Sof(F4B)=0.5*(1-FVAR(2))
 Sof(SbA)=Sof(F3A)=Sof(F4A)=Sof(F2A)=Sof(F6A)=Sof(F1A)=Sof(F5A)=0.5*FVAR(2)
 Sof(C11B)=Sof(C16B)=Sof(H16B)=Sof(C15B)=Sof(H15B)=Sof(C14B)=Sof(C13B)=
 Sof(H13B)=Sof(C12B)=Sof(H12B)=1-FVAR(2)
 Sof(C16A)=Sof(H16A)=Sof(C15A)=Sof(H15A)=Sof(C14A)=Sof(C13A)=Sof(H13A)=
 Sof(C12A)=Sof(H12A)=Sof(C11A)=FVAR(2)
 Sof(C16)=Sof(H16C)=Sof(H16D)=Sof(H16E)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=1-FVAR(3)
 Sof(C13)=Sof(H13C)=Sof(H13D)=Sof(H13E)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(3)
 Fixed Sof: C22A(0.691) H22A(0.691) C23A(0.691) H23A(0.691) C24A(0.691)
 C25A(0.691) H25A(0.691) C26A(0.691) H26A(0.691) C21A(0.691) C29A(0.691)
 H29A(0.691) H29B(0.691) H29C(0.691) C27A(0.691) C30A(0.691) H30A(0.691)
 H30B(0.691) H30C(0.691) C28A(0.691) H28A(0.691) H28B(0.691) H28C(0.691)
 C22B(0.309) H22B(0.309) C23B(0.309) H23B(0.309) C24B(0.309) C25B(0.309)
 H25B(0.309) C26B(0.309) H26B(0.309) C21B(0.309) C27B(0.309) C29B(0.309)
 H29D(0.309) H29E(0.309) H29F(0.309) C30B(0.309) H30D(0.309) H30E(0.309)
 H30F(0.309) C28B(0.309) H28D(0.309) H28E(0.309) H28F(0.309)
7.a Me refined with riding coordinates:
 C28B(H28D,H28E,H28F)
7.b Aromatic/amide H refined with riding coordinates:
 N(H), C2(H2), C3(H3), C6(H6), C8(H8), C22A(H22A), C23A(H23A), C25A(H25A),
 C26A(H26A), C22B(H22B), C23B(H23B), C25B(H25B), C26B(H26B), C16A(H16A),
 C15A(H15A), C13A(H13A), C12A(H12A), C16B(H16B), C15B(H15B), C13B(H13B),
 C12B(H12B)
7.c Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6), C22A(C23A,C24A,C25A,C26A,C21A), C22B(C23B,C24B,C25B,C26B,
 C21B), C16A(C15A,C14A,C13A,C12A,C11A), C11B(C16B,C15B,C14B,C13B,C12B)
7.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C29A(H29A,H29B,H29C), C30A(H30A,H30B,H30C), C28A(H28A,
 H28B,H28C), C29B(H29D,H29E,H29F), C30B(H30D,H30E,H30F), C13(H13C,H13D,H13E),
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C16(H16C,H16D,H16E), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 224 electrons were 
found in a volume of 658\%A^3^ in 2 voids per unit cell. 
This is consistent with the presence of 
2[C4H8O], 1[C4H8O] per Asymmetric Unit 
which account for 240 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              76793
_shelx_fab_checksum              67234
_olex2_submission_special_instructions 'No special instructions were received'
_stoe_detector_distance          '40.0 mm'
_stoe_detector_pixelsize_x       '0.075 mm'
_stoe_detector_pixelsize_y       '0.075 mm'
_stoe_detector_size_x            '8.0 cm'
_stoe_detector_size_y            '7.7 cm'
_stoe_evaluation_integration_a   10.1
_stoe_evaluation_integration_b   -0.1
_stoe_evaluation_integration_ems 0.014
_stoe_evaluation_lana_bis_l_even_max -
_stoe_evaluation_lana_bis_l_odd_max -
_stoe_evaluation_lana_bos_l_even_max 4
_stoe_evaluation_lana_bos_l_odd_max 1
_stoe_evaluation_lana_completeness 80.8
_stoe_evaluation_lana_dxs_max_order 1
_stoe_evaluation_lana_dys_max_order 1
_stoe_evaluation_lana_fs_max_order 3
_stoe_evaluation_lana_max_2theta_available 60.4
_stoe_evaluation_lana_max_2theta_desired 60.4
_stoe_evaluation_lana_mean_redundancy 2.6
_stoe_evaluation_lana_number_refls_after_or 47077
_stoe_evaluation_lana_number_refls_outliers 9161
_stoe_evaluation_lana_number_refls_total 56238
_stoe_evaluation_lana_number_refls_unique 17967
_stoe_evaluation_lana_number_refls_written 47077
_stoe_evaluation_lana_or_c1      0.035
_stoe_evaluation_lana_or_c2      0
_stoe_evaluation_lana_or_c3      0
_stoe_evaluation_lana_or_c4      0.7
_stoe_evaluation_lana_point_group m
_stoe_evaluation_lana_table
;
2Theta           6.6   13.0   19.4   25.8   32.2   38.6   45.0   51.4   57.8
<Resolution>    5.50   2.97   2.06   1.57   1.27   1.07   0.93   0.82   0.75
N(total)         333   1476   3974   6974  10633  11539  10354   8755   2200
<Redundancy>     2.5    2.9    3.6    3.7    3.9    3.2    2.4    1.8    1.3
Complet. [%%]    99.0   98.4   99.9   99.7   99.8   99.5   98.1   90.9   31.5
<I/sigma>       96.3   54.8   32.9   20.6   11.4    7.5    3.5    1.6    0.7
R(int)         0.036  0.028  0.025  0.029  0.042  0.062  0.123  0.215  0.364
;
_stoe_measurement_identifier     NV324
_stoe_measurement_max_exposure_per_frame '10.0 s'
_stoe_measurement_mean_exposure_per_frame '10.0 s'
_stoe_measurement_min_exposure_per_frame '10.0 s'
_stoe_measurement_total_exposure_time '94 min'
_stoe_measurement_total_frame_number 564
_stoe_measurement_total_run_number 14
_stoe_measurement_tube_power     '49.8 W'