Design of a multifunctionalizable BODIPY platform for the facile elaboration of a large series of gold(i)-based optical theranostics.
Pliquett, Jacques; Amor, Souheila; Ponce-Vargas, Miguel; Laly, Myriam; Racoeur, Cindy; Rousselin, Yoann; Denat, Franck; Bettaïeb, Ali; Fleurat-Lessard, Paul; Paul, Catherine; Goze, Christine; Bodio, Ewen; Dalton transactions (Cambridge, England : 2003) 47 (2018) 11203–11218; doi:10.1039/c8dt02364f

data_7047040
_publ_section_title
;
 Design of a multifunctionalizable BODIPY platform for the facile
 elaboration of a large series of gold(i)-based optical theranostics.
;
_journal_issue                   32
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11203
_journal_page_last               11218
_journal_paper_doi               10.1039/c8dt02364f
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety
'0.5(C58 H48 Au2 B2 Cl4 F4 N6 P2), 1(C H2 Cl2)'
_chemical_formula_sum            'C30 H26 Au B Cl4 F2 N3 P'
_chemical_formula_weight         847.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-02-26
_audit_creation_method
;
Olex2 1.2
(compiled Aug 10 2017 17:28:52 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-02-26 deposited with the CCDC.
2018-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.500(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.9927(4)
_cell_length_b                   29.9994(8)
_cell_length_c                   15.2788(5)
_cell_measurement_reflns_used    9812
_cell_measurement_temperature    115(1)
_cell_measurement_theta_max      27.472
_cell_measurement_theta_min      2.480
_cell_volume                     6384.1(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      115(1)
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_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_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            113257
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.617
_diffrn_reflns_theta_min         2.438
_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    5.031
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1361 before and 0.0534 after correction.
The Ratio of minimum to maximum transmission is 0.6090.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_description       prism
_exptl_crystal_F_000             3296
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM and hexane by slow evaporation'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.312
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     774
_refine_ls_number_reflns         14774
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0252
_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^)+(0.0142P)^2^+12.8578P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0489
_refine_ls_wR_factor_ref         0.0542
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12297
_reflns_number_total             14774
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt02364f2.cif
_cod_data_source_block           BODI_Au_7
_cod_depositor_comments
'Adding full bibliography for 7047037--7047040.cif.'
_cod_database_code               7047040
_publcif_datablock.id            {26261bbf-df25-4f70-8a9e-cc35b1dbf5ef}
_shelx_shelxl_version_number     2018/1
_shelx_estimated_absorpt_t_max   0.465
_shelx_estimated_absorpt_t_min   0.244
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Rigid body (RIGU) restrains
 C53, C58, C57, C56, C55, C54
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
3. Others
 1*[Sof(Cl1A)+Sof(Cl2A)+Sof(C1A)+Sof(H1AA)+Sof(H1AB)]+1*[Sof(Cl1B)+Sof(Cl2B)+
 Sof(C1B)+Sof(H1BA)+Sof(H1BB)]+1*[Sof(Cl1C)+Sof(Cl2C)+Sof(C1C)+Sof(H1CA)+
 Sof(H1CB)]=1 with esd of 0.0001
 1*[Sof(Cl1D)+Sof(Cl2D)+Sof(C1D)+Sof(H1DA)+Sof(H1DB)]+1*[Sof(Cl1E)+Sof(Cl2E)+
 Sof(C1E)+Sof(H1EA)+Sof(H1EB)]+1*[Sof(Cl1F)+Sof(Cl2F)+Sof(C1F)+Sof(H1FA)+
 Sof(H1FB)]=1 with esd of 0.0001
 Sof(C53A)=Sof(C58A)=Sof(H58A)=Sof(C57A)=Sof(H57A)=Sof(C56A)=Sof(H56A)=
 Sof(C55A)=Sof(H55A)=Sof(C54A)=Sof(H54A)=1-FVAR(1)
 Sof(C53)=Sof(C58)=Sof(H58)=Sof(C57)=Sof(H57)=Sof(C56)=Sof(H56)=Sof(C55)=
 Sof(H55)=Sof(C54)=Sof(H54)=FVAR(1)
 Sof(Cl1A)=Sof(Cl2A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=FVAR(2)
 Sof(Cl1B)=Sof(Cl2B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=FVAR(3)
 Sof(Cl1C)=Sof(Cl2C)=Sof(C1C)=Sof(H1CA)=Sof(H1CB)=FVAR(4)
 Sof(Cl1D)=Sof(Cl2D)=Sof(C1D)=Sof(H1DA)=Sof(H1DB)=FVAR(5)
 Sof(Cl1E)=Sof(Cl2E)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=FVAR(6)
 Sof(Cl1F)=Sof(Cl2F)=Sof(C1F)=Sof(H1FA)=Sof(H1FB)=FVAR(7)
 Uiso(Cl1F)=Uiso(Cl2F)=Uiso(C1F)=Uiso(Cl1C)=Uiso(Cl2C)=Uiso(C1C)=FVAR(8)
4.a Free rotating group:
 Cl1D(Cl2D,C1D), Cl1F(Cl2F,C1F), Cl1A(Cl2A,C1A), Cl1C(Cl2C,C1C), Cl1E(Cl2E,
 C1E), Cl1B(Cl2B,C1B)
4.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C42(H42A,H42B), C43(H43A,H43B), C1D(H1DA,
 H1DB), C1F(H1FA,H1FB), C1A(H1AA,H1AB), C1C(H1CA,H1CB), C1E(H1EA,H1EB),
 C1B(H1BA,H1BB)
4.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N6(H6), C2(H2), C3(H3A), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C13(H13), C14(H14), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
  C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C32(H32), C33(H33),
 C34(H34), C35(H35), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41), C45(H45),
  C46(H46), C50(H50), C51(H51), C58(H58), C57(H57), C56(H56), C55(H55),
 C54(H54), C58A(H58A), C57A(H57A), C56A(H56A), C55A(H55A), C54A(H54A)
4.d Fitted hexagon refined as free rotating group:
 C53(C58,C57,C56,C55,C54), C53A(C58A,C57A,C56A,C55A,C54A)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder oil'
_olex2_submission_special_instructions 'No special instructions were received'