Esterification of the free carboxylic group from the lutidinic acid ligand as a tool to improve the cytotoxicity of Ru(ii) complexes
Honorato, João; Colina-Vegas, Legna; Correa, Rodrigo S.; Guedes, Adriana P. M.; Miyata, Marcelo; Pavan, Fernando R.; Ellena, Javier; Batista, Alzir A.; Inorganic Chemistry Frontiers 6 (2019) 376–; doi:10.1039/C8QI00941D

data_4349916
_publ_section_title
;
 Esterification of the free carboxylic group from the lutidinic acid
 ligand as a tool to improve the cytotoxicity of Ru(ii) complexes
;
_journal_issue                   2
_journal_name_full               'Inorganic Chemistry Frontiers'
_journal_page_first              376
_journal_paper_doi               10.1039/C8QI00941D
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C47 H44 N3 O4 P2 Ru, F6 P'
_chemical_formula_sum            'C47 H44 F6 N3 O4 P3 Ru'
_chemical_formula_weight         1022.83
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-11-09 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.746(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.5183(4)
_cell_length_b                   12.8666(3)
_cell_length_c                   28.1285(7)
_cell_measurement_reflns_used    28762
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.4760
_cell_measurement_theta_min      2.8080
_cell_volume                     4806.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      298.0
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -69.00 118.00   1.00   20.00    --   27.63  54.00   0.00  187
  2  \w    -69.00 118.00   1.00   20.00    --   27.63  54.00-120.00  187
  3  \w    -69.00 118.00   1.00   20.00    --   27.63  54.00-120.00  187
  4  \w    -69.00 118.00   1.00   20.00    --   27.63  54.00  90.00  187
  5  \w    -69.00 118.00   1.00   20.00    --   27.63  54.00   0.00  187
  6  \w    -69.00  40.00   1.00   20.00    --   27.63  54.00-180.00  109
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0134102000
_diffrn_orient_matrix_UB_12      0.0529609000
_diffrn_orient_matrix_UB_13      0.0042211000
_diffrn_orient_matrix_UB_21      -0.0492922000
_diffrn_orient_matrix_UB_22      0.0152108000
_diffrn_orient_matrix_UB_23      -0.0111987000
_diffrn_orient_matrix_UB_31      -0.0155448000
_diffrn_orient_matrix_UB_32      -0.0024206000
_diffrn_orient_matrix_UB_33      0.0226974000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            117587
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.719
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92523
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       prism
_exptl_crystal_F_000             2088
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.360
_refine_diff_density_min         -0.949
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     574
_refine_ls_number_reflns         14670
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0548
_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^)+(0.0644P)^2^+8.9302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1385
_refine_ls_wR_factor_ref         0.1617
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11326
_reflns_number_total             14670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qi00941d2.cif
_cod_data_source_block           cb24e
_cod_database_code               4349916
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C30 H35 O4 N3 P3 F6 Ru1'
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.903
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. 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
2. Uiso/Uaniso restraints and constraints
Uanis(F1') = Uanis(F3') = Uanis(F5') = Uanis(F2') = Uanis(F6') = Uanis(F4')
Uanis(F1) = Uanis(F4) = Uanis(F6) = Uanis(F5) = Uanis(F2) = Uanis(F3)
3. Others
 Sof(F5)=Sof(F4)=Sof(F1)=1-FVAR(1)
 Sof(F2)=Sof(F6)=Sof(F3)=FVAR(1)
 Sof(F5')=Sof(F2')=Sof(F6')=1-FVAR(2)
 Sof(F1')=Sof(F3')=Sof(F4')=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C131(H13A,H13B), C232(H23A,H23B), C231(H23C,H23D), C132(H13C,H13D), C17(H17A,
 H17B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C212(H212), C11(H11), C14(H14), C2(H2), C12(H12), C122(H122),
 C10(H10), C226(H226), C126(H126), C213(H213), C112(H112), C4(H4), C116(H116),
 C216(H216), C9(H9), C3(H3), C7(H7), C125(H125), C113(H113), C222(H222),
 C114(H114), C225(H225), C115(H115), C8(H8), C214(H214), C215(H215), C123(H123),
  C223(H223), C224(H224), C124(H124)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 1.093
_oxdiff_exptl_absorpt_empirical_full_min 0.931