#------------------------------------------------------------------------------
#$Date: 2020-12-02 05:56:04 +0100 (Wed 02 de Dec de 2020) $
#$Revision: 259428 $
#$URL: svn://www.crystallography.net/cod/cif/7/06/01/7060107.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_7060107
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 H11 F N2 O2'
_chemical_formula_sum            'C13 H11 F N2 O2'
_chemical_formula_weight         246.24
_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'
_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                 107.930(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7343(10)
_cell_length_b                   13.7655(14)
_cell_length_c                   9.5215(10)
_cell_measurement_reflns_used    8043
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4821
_cell_measurement_theta_min      2.6507
_cell_measurement_wavelength     0.710730
_cell_volume                     1213.9(2)
_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 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_orient_matrix_UB_11      0.0947509
_diffrn_orient_matrix_UB_12      -0.0361328
_diffrn_orient_matrix_UB_13      0.0414609
_diffrn_orient_matrix_UB_21      0.0441069
_diffrn_orient_matrix_UB_22      0.0582566
_diffrn_orient_matrix_UB_23      0.0589077
_diffrn_orient_matrix_UB_31      -0.0355262
_diffrn_orient_matrix_UB_32      -0.0240412
_diffrn_orient_matrix_UB_33      0.0804312
_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  0.0380
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10320
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_min         2.199
_diffrn_source_current           1.0
_diffrn_source_voltage           55.0
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.769
_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    1.347
_exptl_crystal_description       prism
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.390
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.033(3)
_refine_ls_extinction_method     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2762
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0386P)²+0.9826P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                2371
_reflns_number_total             2762
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0nj05334a2.cif
_cod_data_source_block           MW285
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7060107
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
F1 F 0.26304(13) 0.03288(7) 0.54284(12) 0.0365(3) Uani 1 1 d . . . . .
C2 C 0.34600(19) 0.11264(12) 0.54614(18) 0.0257(4) Uani 1 1 d . . . . .
C3 C 0.4893(2) 0.10872(14) 0.6301(2) 0.0360(4) Uani 1 1 d . . . . .
H3 H 0.529181 0.051653 0.683165 0.043 Uiso 1 1 calc R U . . .
C4 C 0.5732(2) 0.19040(16) 0.6345(3) 0.0450(5) Uani 1 1 d . . . . .
H4 H 0.672102 0.189789 0.692097 0.054 Uiso 1 1 calc R U . . .
C5 C 0.5146(2) 0.27322(14) 0.5558(2) 0.0377(5) Uani 1 1 d . . . . .
H5 H 0.572745 0.328938 0.557939 0.045 Uiso 1 1 calc R U . . .
C6 C 0.36996(17) 0.27330(11) 0.47432(18) 0.0239(3) Uani 1 1 d . . . . .
C7 C 0.28244(17) 0.19340(12) 0.46728(17) 0.0232(3) Uani 1 1 d . . . . .
H7 H 0.183204 0.194088 0.410808 0.028 Uiso 1 1 calc R U . . .
O8 O 0.31112(13) 0.35667(8) 0.39329(12) 0.0265(3) Uani 1 1 d . . . . .
C9 C 0.25525(16) 0.42575(11) 0.46363(16) 0.0195(3) Uani 1 1 d . . . . .
C10 C 0.24612(17) 0.41548(11) 0.60584(16) 0.0211(3) Uani 1 1 d . . . . .
H10 H 0.278264 0.358048 0.661610 0.025 Uiso 1 1 calc R U . . .
C11 C 0.18823(17) 0.49240(11) 0.66294(16) 0.0216(3) Uani 1 1 d . . . . .
H11 H 0.180420 0.485260 0.759430 0.026 Uiso 1 1 calc R U . . .
N12 N 0.14265(14) 0.57580(9) 0.59222(13) 0.0196(3) Uani 1 1 d . . . . .
C13 C 0.15134(15) 0.58272(10) 0.45421(15) 0.0171(3) Uani 1 1 d . . . . .
C14 C 0.20566(16) 0.51056(11) 0.38523(16) 0.0189(3) Uani 1 1 d . . . . .
H14 H 0.208989 0.518703 0.287249 0.023 Uiso 1 1 calc R U . . .
C15 C 0.09772(16) 0.67587(11) 0.37200(16) 0.0184(3) Uani 1 1 d . . . . .
O16 O 0.08145(14) 0.68125(8) 0.23796(12) 0.0281(3) Uani 1 1 d . . . . .
N17 N 0.07190(14) 0.74816(9) 0.45201(14) 0.0203(3) Uani 1 1 d . . . . .
H17 H 0.086(2) 0.7396(14) 0.546(2) 0.024 Uiso 1 1 d . U . . .
C18 C 0.0217(2) 0.84282(11) 0.38923(18) 0.0267(4) Uani 1 1 d . . . . .
H18A H 0.065715 0.858265 0.312172 0.040 Uiso 1 1 calc R U . . .
H18B H 0.049234 0.892289 0.466900 0.040 Uiso 1 1 calc R U . . .
H18C H -0.083600 0.841705 0.346308 0.040 Uiso 1 1 calc R U . . .
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
F1 C2 C7 118.43(15) . . ?
F1 C2 C3 118.06(15) . . ?
C7 C2 C3 123.51(16) . . ?
C2 C3 C4 117.94(17) . . ?
C2 C3 H3 121.0 . . ?
C4 C3 H3 121.0 . . ?
C3 C4 C5 120.72(18) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.86(17) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C7 C6 C5 122.23(15) . . ?
C7 C6 O8 118.93(14) . . ?
C5 C6 O8 118.83(15) . . ?
C2 C7 C6 116.73(15) . . ?
C2 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C9 O8 C6 117.11(12) . . ?
O8 C9 C14 116.46(13) . . ?
O8 C9 C10 124.04(13) . . ?
C14 C9 C10 119.51(14) . . ?
C11 C10 C9 117.35(14) . . ?
C11 C10 H10 121.3 . . ?
C9 C10 H10 121.3 . . ?
N12 C11 C10 124.79(14) . . ?
N12 C11 H11 117.6 . . ?
C10 C11 H11 117.6 . . ?
C11 N12 C13 116.23(13) . . ?
N12 C13 C14 124.14(13) . . ?
N12 C13 C15 116.80(13) . . ?
C14 C13 C15 119.06(13) . . ?
C13 C14 C9 117.95(13) . . ?
C13 C14 H14 121.0 . . ?
C9 C14 H14 121.0 . . ?
O16 C15 N17 124.15(14) . . ?
O16 C15 C13 119.95(13) . . ?
N17 C15 C13 115.90(13) . . ?
C15 N17 C18 122.44(13) . . ?
C15 N17 H17 119.5(13) . . ?
C18 N17 H17 118.1(13) . . ?
N17 C18 H18A 109.5 . . ?
N17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
F1 C2 1.3575(19) . ?
C2 C7 1.377(2) . ?
C2 C3 1.379(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.380(2) . ?
C6 O8 1.4029(19) . ?
C7 H7 0.9500 . ?
O8 C9 1.3685(18) . ?
C9 C14 1.390(2) . ?
C9 C10 1.391(2) . ?
C10 C11 1.387(2) . ?
C10 H10 0.9500 . ?
C11 N12 1.3358(19) . ?
C11 H11 0.9500 . ?
N12 C13 1.3459(19) . ?
C13 C14 1.383(2) . ?
C13 C15 1.509(2) . ?
C14 H14 0.9500 . ?
C15 O16 1.2389(18) . ?
C15 N17 1.324(2) . ?
N17 C18 1.4540(19) . ?
N17 H17 0.87(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
F1 C2 C3 C4 -179.31(18) . . . . ?
C7 C2 C3 C4 -0.2(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C4 C5 C6 O8 -179.21(18) . . . . ?
F1 C2 C7 C6 179.48(14) . . . . ?
C3 C2 C7 C6 0.3(2) . . . . ?
C5 C6 C7 C2 0.1(2) . . . . ?
O8 C6 C7 C2 178.59(14) . . . . ?
C7 C6 O8 C9 91.82(17) . . . . ?
C5 C6 O8 C9 -89.66(19) . . . . ?
C6 O8 C9 C14 176.07(13) . . . . ?
C6 O8 C9 C10 -3.9(2) . . . . ?
O8 C9 C10 C11 179.28(14) . . . . ?
C14 C9 C10 C11 -0.6(2) . . . . ?
C9 C10 C11 N12 -1.0(2) . . . . ?
C10 C11 N12 C13 1.8(2) . . . . ?
C11 N12 C13 C14 -1.1(2) . . . . ?
C11 N12 C13 C15 178.94(13) . . . . ?
N12 C13 C14 C9 -0.4(2) . . . . ?
C15 C13 C14 C9 179.57(13) . . . . ?
O8 C9 C14 C13 -178.66(13) . . . . ?
C10 C9 C14 C13 1.3(2) . . . . ?
N12 C13 C15 O16 -168.69(14) . . . . ?
C14 C13 C15 O16 11.3(2) . . . . ?
N12 C13 C15 N17 11.81(19) . . . . ?
C14 C13 C15 N17 -168.18(13) . . . . ?
O16 C15 N17 C18 -0.3(2) . . . . ?
C13 C15 N17 C18 179.14(13) . . . . ?
