Gold(I)-BODIPY-imidazole bimetallic complexes as new potential anti-inflammatory and anticancer trackable agents
Trommenschlager, Audrey; Chotard, Florian; Bertrand, Benoît; Amor, Souheila; Dondaine, Lucile; Picquet, Michel; Richard, Philippe; Bettaeib, Ali; Le Gendre, Pierre; Paul, Catherine; Goze, Christine; Bodio, Ewen; Dalton Trans.  (2017) –; doi:10.1039/C7DT01377A

data_7043058
_publ_section_title
;
 Gold(I)-BODIPY-imidazole bimetallic complexes as new potential
 anti-inflammatory and anticancer trackable agents
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT01377A
_journal_year                    2017
_chemical_formula_moiety         '2.5(C21 H15 B F2 N6), 0.5(C H2 Cl2)'
_chemical_formula_sum            'C53 H38.5 B2.5 Cl F5 N15'
_chemical_formula_weight         1042.96
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-03-15 deposited with the CCDC.
2017-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0671(5)
_cell_length_b                   32.4681(14)
_cell_length_c                   12.0173(5)
_cell_measurement_reflns_used    9730
_cell_measurement_temperature    150
_cell_measurement_theta_max      23.148
_cell_measurement_theta_min      2.39
_cell_volume                     4708.3(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans''
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0722
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            144944
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         3.025
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0813 before and 0.0749 after correction. The Ratio of minimum to maximum transmission is 0.8782. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_description       plate
_exptl_crystal_F_000             2144
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 3442 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     730
_refine_ls_number_reflns         10767
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+2.3893P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1380
_reflns_Friedel_coverage         0.805
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                9045
_reflns_number_total             10767
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7dt01377a3.cif
_cod_data_source_block           aud100217_0ma_a
_cod_original_formula_sum        'C53 H38.50 B2.50 Cl F5 N15'
_cod_database_code               7043058
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.924
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 N3B, N3, C16B, C18, N4, C17B, C17, N4B, C16, C18B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(N3B)=Sof(C18B)=Sof(H18B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=Sof(H17B)=Sof(N4B)=
 1-FVAR(1)
 Sof(N3)=Sof(C18)=Sof(H18)=Sof(C16)=Sof(H16)=Sof(C17)=Sof(H17)=Sof(N4)=FVAR(1)
 Fixed Sof: Cl1(0.5) Cl2(0.5) C55(0.5) H55A(0.5) H55B(0.5)
4.a Free rotating group:
 N3(C18,C16,C17,N4), N3B(C18B,C16B,C17B,N4B), Cl1(Cl2,C55)
4.b Secondary CH2 refined with riding coordinates:
 C55(H55A,H55B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C19(H19), C20(H20), C21(H21), C18(H18), C16(H16), C17(H17),
 C18B(H18B), C16B(H16B), C17B(H17B), C23(H23), C24(H24), C28(H28), C29(H29),
 C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39),
  C40(H40), C41(H41), C42(H42), C44(H44), C45(H45), C49(H49), C50(H50),
 C51(H51), C52(H52), C53(H53), C54(H54)
;
_olex2_submission_special_instructions 'No special instructions were received'