#------------------------------------------------------------------------------
#$Date: 2020-12-02 06:56:04 +0200 (Wed, 02 Dec 2020) $
#$Revision: 259428 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/01/7060106.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7060106
loop_
_publ_author_name
'Wilde, Myron'
'Arzur, Danielle'
'Baratte, Blandine'
'Lefebvre, Dorian'
'Robert, Thomas'
'Roisnel, Thierry'
'Le Jossic-Corcos, Catherine'
'Bach, Stéphane'
'Corcos, Laurent'
'Erb, William'
_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_compound_source        'synthesis as described'
_chemical_formula_moiety         'C13 H12 F N3 O2'
_chemical_formula_sum            'C13 H12 F N3 O2'
_chemical_formula_weight         261.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                108.895(3)
_cell_angle_beta                 99.835(3)
_cell_angle_gamma                97.095(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2126(7)
_cell_length_b                   7.7988(7)
_cell_length_c                   11.6303(11)
_cell_measurement_reflns_used    8607
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.5084
_cell_measurement_theta_min      2.8128
_cell_measurement_wavelength     0.710730
_cell_volume                     598.52(10)
_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, 2020)'
_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 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0548299
_diffrn_orient_matrix_UB_12      -0.1083369
_diffrn_orient_matrix_UB_13      -0.0434647
_diffrn_orient_matrix_UB_21      0.0971617
_diffrn_orient_matrix_UB_22      0.0240543
_diffrn_orient_matrix_UB_23      0.0786260
_diffrn_orient_matrix_UB_31      -0.0900579
_diffrn_orient_matrix_UB_32      -0.0821837
_diffrn_orient_matrix_UB_33      0.0250267
_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  0.0275
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11230
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.508
_diffrn_reflns_theta_min         2.813
_diffrn_source_current           1.0
_diffrn_source_voltage           55.0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_description       prism
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.056(9)
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0424
_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/[σ²(Fo²)+(0.0643P)²+0.3934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1229
_reflns_number_gt                2411
_reflns_number_total             2726
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0nj05334a2.cif
_cod_data_source_block           MW1404
_cod_database_code               7060106
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4331(2) 0.22854(18) 0.49357(13) 0.0210(3) Uani 1 1 d . . . . .
H1 H 0.559093 0.210102 0.519176 0.025 Uiso 1 1 calc R U . . .
C2 C 0.3874(2) 0.29279(18) 0.39706(12) 0.0212(3) Uani 1 1 d . . . . .
C5 C 0.1055(2) 0.22156(19) 0.51571(13) 0.0217(3) Uani 1 1 d . . . . .
H5 H 0.008089 0.196666 0.556905 0.026 Uiso 1 1 calc R U . A 1
C6 C 0.2888(2) 0.19176(18) 0.55195(12) 0.0195(3) Uani 1 1 d . . . . .
F7 F 0.52499(15) 0.32233(14) 0.33530(9) 0.0370(3) Uani 1 1 d . . . . .
C3A C 0.2056(2) 0.32292(18) 0.35536(12) 0.0213(3) Uani 0.901(3) 1 d . . P B 1
C4A C 0.0660(2) 0.28793(19) 0.41893(13) 0.0220(3) Uani 0.901(3) 1 d . . P B 1
H4A H -0.058950 0.310160 0.395259 0.026 Uiso 0.901(3) 1 calc R U P B 1
N9A N 0.1672(3) 0.3878(2) 0.25694(13) 0.0241(3) Uani 0.901(3) 1 d . . P B 1
H9A H 0.065(3) 0.364(3) 0.226(2) 0.029 Uiso 0.9015 1 d . U P B 1
H9B H 0.233(3) 0.371(3) 0.219(2) 0.029 Uiso 0.9015 1 d . U P B 1
C3B C 0.2056(2) 0.32292(18) 0.35536(12) 0.0213(3) Uani 0.099(3) 1 d . . P B 2
H3B H 0.178069 0.364977 0.287379 0.026 Uiso 0.099(3) 1 calc R U P B 2
C4B C 0.0660(2) 0.28793(19) 0.41893(13) 0.0220(3) Uani 0.099(3) 1 d . . P B 2
N9B N -0.1096(19) 0.3125(17) 0.3839(11) 0.0241(3) Uani 0.099(3) 1 d . . P B 2
H9B1 H -0.199171 0.286821 0.421814 0.029 Uiso 0.099(3) 1 calc R U P B 2
H9B2 H -0.137182 0.354536 0.322588 0.029 Uiso 0.099(3) 1 calc R U P B 2
O9 O 0.33057(17) 0.10633(14) 0.63980(9) 0.0253(3) Uani 1 1 d . . . C 2
C10 C 0.30596(19) 0.18622(18) 0.75821(12) 0.0175(3) Uani 1 1 d . . . C 2
C11 C 0.31445(19) 0.07703(18) 0.83168(13) 0.0185(3) Uani 1 1 d . . . C 2
H11 H 0.329590 -0.047605 0.798882 0.022 Uiso 1 1 calc R U . C 2
C12 C 0.3002(2) 0.15520(19) 0.95421(13) 0.0203(3) Uani 1 1 d . . . C 2
H12 H 0.308490 0.081254 1.005024 0.024 Uiso 1 1 calc R U . C 2
N13 N 0.27539(16) 0.32932(16) 1.00561(10) 0.0190(3) Uani 1 1 d . . . C 2
C14 C 0.26413(17) 0.43038(17) 0.93195(12) 0.0157(3) Uani 1 1 d . . . C 2
C15 C 0.27997(18) 0.36743(18) 0.80827(12) 0.0167(3) Uani 1 1 d . . . C 2
H15 H 0.273338 0.444920 0.759881 0.020 Uiso 1 1 calc R U . C 2
C16 C 0.23289(18) 0.62559(18) 0.98803(12) 0.0173(3) Uani 1 1 d . . . C 2
O17 O 0.21670(16) 0.72568(14) 0.92513(10) 0.0252(3) Uani 1 1 d . . . C 2
N18 N 0.22293(17) 0.67764(16) 1.10787(11) 0.0198(3) Uani 1 1 d . . . C 2
H18 H 0.237(3) 0.601(3) 1.1471(17) 0.024 Uiso 1 1 d . U . D 2
C19 C 0.1973(2) 0.86181(19) 1.17692(14) 0.0240(3) Uani 1 1 d . . . C 2
H19A H 0.318922 0.949099 1.199477 0.036 Uiso 1 1 calc R U . C 2
H19B H 0.155736 0.861664 1.252849 0.036 Uiso 1 1 calc R U . C 2
H19C H 0.099800 0.898873 1.125009 0.036 Uiso 1 1 calc R U . C 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.64(13) . . ?
C2 C1 H1 121.2 . . ?
C6 C1 H1 121.2 . . ?
F7 C2 C1 118.45(13) . . ?
F7 C2 C3B 117.61(12) . . ?
C1 C2 C3B 123.89(13) . . ?
F7 C2 C3A 117.61(12) . . ?
C1 C2 C3A 123.89(13) . . ?
C4B C5 C6 119.41(13) . . ?
C4A C5 C6 119.41(13) . . ?
C4A C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 121.11(12) . . ?
C1 C6 O9 117.10(12) . . ?
C5 C6 O9 121.48(12) . . ?
C2 C3A N9A 121.46(14) . . ?
C2 C3A C4A 116.40(12) . . ?
N9A C3A C4A 122.13(14) . . ?
C5 C4A C3A 121.53(13) . . ?
C5 C4A H4A 119.2 . . ?
C3A C4A H4A 119.2 . . ?
C3A N9A H9A 112.7(18) . . ?
C3A N9A H9B 112.4(19) . . ?
H9A N9A H9B 117(3) . . ?
C2 C3B C4B 116.40(12) . . ?
C2 C3B H3B 121.8 . . ?
C4B C3B H3B 121.8 . . ?
N9B C4B C5 118.8(5) . . ?
N9B C4B C3B 119.6(5) . . ?
C5 C4B C3B 121.53(13) . . ?
C4B N9B H9B1 120.0 . . ?
C4B N9B H9B2 120.0 . . ?
H9B1 N9B H9B2 120.0 . . ?
C10 O9 C6 119.77(10) . . ?
O9 C10 C11 115.96(11) . . ?
O9 C10 C15 124.34(12) . . ?
C11 C10 C15 119.67(12) . . ?
C12 C11 C10 117.99(12) . . ?
C12 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
N13 C12 C11 123.94(12) . . ?
N13 C12 H12 118.0 . . ?
C11 C12 H12 118.0 . . ?
C14 N13 C12 116.78(11) . . ?
N13 C14 C15 124.24(12) . . ?
N13 C14 C16 117.32(11) . . ?
C15 C14 C16 118.44(11) . . ?
C14 C15 C10 117.35(12) . . ?
C14 C15 H15 121.3 . . ?
C10 C15 H15 121.3 . . ?
O17 C16 N18 123.87(12) . . ?
O17 C16 C14 121.05(12) . . ?
N18 C16 C14 115.08(11) . . ?
C16 N18 C19 122.29(12) . . ?
C16 N18 H18 119.3(12) . . ?
C19 N18 H18 118.4(12) . . ?
N18 C19 H19A 109.5 . . ?
N18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3778(19) . ?
C1 C6 1.3857(19) . ?
C1 H1 0.9500 . ?
C2 F7 1.3594(16) . ?
C2 C3B 1.394(2) . ?
C2 C3A 1.394(2) . ?
C5 C4B 1.3858(19) . ?
C5 C4A 1.3858(19) . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 O9 1.4013(15) . ?
C3A N9A 1.3946(18) . ?
C3A C4A 1.397(2) . ?
C4A H4A 0.9500 . ?
N9A H9A 0.74(2) . ?
N9A H9B 0.70(2) . ?
C3B C4B 1.397(2) . ?
C3B H3B 0.9500 . ?
C4B N9B 1.319(13) . ?
N9B H9B1 0.8800 . ?
N9B H9B2 0.8800 . ?
O9 C10 1.3680(15) . ?
C10 C11 1.3876(18) . ?
C10 C15 1.3932(18) . ?
C11 C12 1.3841(19) . ?
C11 H11 0.9500 . ?
C12 N13 1.3432(18) . ?
C12 H12 0.9500 . ?
N13 C14 1.3383(16) . ?
C14 C15 1.3913(18) . ?
C14 C16 1.5119(18) . ?
C15 H15 0.9500 . ?
C16 O17 1.2334(16) . ?
C16 N18 1.3369(17) . ?
N18 C19 1.4532(17) . ?
N18 H18 0.865(19) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F7 -177.31(12) . . . . ?
C6 C1 C2 C3B 0.1(2) . . . . ?
C6 C1 C2 C3A 0.1(2) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C2 C1 C6 O9 172.71(11) . . . . ?
C4B C5 C6 C1 0.5(2) . . . . ?
C4A C5 C6 C1 0.5(2) . . . . ?
C4B C5 C6 O9 -173.00(12) . . . . ?
F7 C2 C3A N9A -2.4(2) . . . . ?
C1 C2 C3A N9A -179.86(13) . . . . ?
F7 C2 C3A C4A 178.75(12) . . . . ?
C1 C2 C3A C4A 1.3(2) . . . . ?
C6 C5 C4A C3A 1.0(2) . . . . ?
C2 C3A C4A C5 -1.9(2) . . . . ?
N9A C3A C4A C5 179.30(13) . . . . ?
F7 C2 C3B C4B 178.75(12) . . . . ?
C1 C2 C3B C4B 1.3(2) . . . . ?
C6 C5 C4B N9B 178.8(6) . . . . ?
C6 C5 C4B C3B 1.0(2) . . . . ?
C2 C3B C4B N9B -179.6(6) . . . . ?
C2 C3B C4B C5 -1.9(2) . . . . ?
C1 C6 O9 C10 125.11(14) . . . . ?
C5 C6 O9 C10 -61.17(18) . . . . ?
C6 O9 C10 C11 168.01(12) . . . . ?
C6 O9 C10 C15 -14.1(2) . . . . ?
O9 C10 C11 C12 176.74(12) . . . . ?
C15 C10 C11 C12 -1.23(19) . . . . ?
C10 C11 C12 N13 1.2(2) . . . . ?
C11 C12 N13 C14 0.0(2) . . . . ?
C12 N13 C14 C15 -1.23(19) . . . . ?
C12 N13 C14 C16 179.01(11) . . . . ?
N13 C14 C15 C10 1.1(2) . . . . ?
C16 C14 C15 C10 -179.10(11) . . . . ?
O9 C10 C15 C14 -177.63(12) . . . . ?
C11 C10 C15 C14 0.16(19) . . . . ?
N13 C14 C16 O17 -178.35(12) . . . . ?
C15 C14 C16 O17 1.87(19) . . . . ?
N13 C14 C16 N18 1.07(17) . . . . ?
C15 C14 C16 N18 -178.71(11) . . . . ?
O17 C16 N18 C19 -1.9(2) . . . . ?
C14 C16 N18 C19 178.73(11) . . . . ?
