Regorafenib analogues and their ferrocenic counterparts: synthesis and biological evaluation
Wilde, Myron; Arzur, Danielle; Baratte, Blandine; Lefebvre, Dorian; Robert, Thomas; Roisnel, Thierry; Le Jossic-Corcos, Catherine; Bach, Stéphane; Corcos, Laurent; Erb, William; New Journal of Chemistry 44 (2020) 19723–19733; doi:10.1039/D0NJ05334A

data_7060109
_publ_section_title
;
 Regorafenib analogues and their ferrocenic counterparts: synthesis and
 biological evaluation
;
_journal_issue                   45
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19723
_journal_page_last               19733
_journal_paper_doi               10.1039/D0NJ05334A
_journal_volume                  44
_journal_year                    2020
_chemical_absolute_configuration rm/ad/rmad/syn/unk/.
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H13 Cl Fe N2 O'
_chemical_formula_sum            'C16 H13 Cl Fe N2 O'
_chemical_formula_weight         340.58
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-07-17 deposited with the CCDC.	2020-11-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2083(11)
_cell_length_b                   9.7083(8)
_cell_length_c                   10.6102(7)
_cell_measurement_reflns_used    9377
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4831
_cell_measurement_theta_min      2.6037
_cell_measurement_wavelength     0.710730
_cell_volume                     1360.55(18)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      -0.0858577
_diffrn_orient_matrix_UB_12      -0.0275747
_diffrn_orient_matrix_UB_13      0.0354809
_diffrn_orient_matrix_UB_21      -0.0411974
_diffrn_orient_matrix_UB_22      -0.0250359
_diffrn_orient_matrix_UB_23      -0.0664123
_diffrn_orient_matrix_UB_31      0.0392584
_diffrn_orient_matrix_UB_32      -0.0865781
_diffrn_orient_matrix_UB_33      0.0079040
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24782
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.604
_diffrn_source_current           1.0
_diffrn_source_voltage           55.0
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
Flack x determined using 1249 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.007(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2980
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0236
_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^)+(0.0495P)^2^+0.6072P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0633
_refine_ls_wR_factor_ref         0.0649
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.903
_reflns_number_gt                2882
_reflns_number_total             2980
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0nj05334a2.cif
_cod_data_source_block           MW139pur
_cod_database_code               7060109
_shelx_res_checksum              30712