#------------------------------------------------------------------------------
#$Date: 2017-07-25 12:39:10 +0300 (Tue, 25 Jul 2017) $
#$Revision: 199158 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/21/2242188.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2242188
loop_
_publ_author_name
'Martins, Bianca Barreto'
'Bresolin, Leandro'
'de Farias, Renan Lira'
'de Oliveira, Adriano Bof'
'Gervini, Vanessa Carratu'
_publ_section_title
;
 Crystal structure, Hirshfeld analysis and molecular docking with the
 vascular endothelial growth factor receptor-2 of
 (3Z)-5-fluoro-3-(hydroxyimino)indolin-2-one
;
_journal_coeditor_code           RZ5215
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              987
_journal_page_last               992
_journal_paper_doi               10.1107/S2056989017008301
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C8 H5 F N2 O2'
_chemical_formula_moiety         'C8 H5 F N2 O2'
_chemical_formula_sum            'C8 H5 F N2 O2'
_chemical_formula_weight         180.14
_chemical_name_common            5-Fluoroisatin-3-oxime
_chemical_name_systematic
;
(3Z)-5-Fluoro-3-(hydroxyimino)indolin-2-one
;
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 94.736(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3036(10)
_cell_length_b                   7.2045(10)
_cell_length_c                   14.009(2)
_cell_measurement_reflns_used    3387
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      30.03
_cell_measurement_theta_min      2.80
_cell_volume                     734.62(18)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2006), GOLD (Chen et al.,
2015),
MOPAC (Stewart, 2016), CRYSTAL EXPLORER (Wolff, et
al.,
2012)
;
_computing_publication_material
;
publCIF (Westrip, 2010), enCIFer (Allen et al.,
2004)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015b), WinGX (Farrugia,
2012)
;
_computing_structure_solution
;
SHELXT2014/4 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8386
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.053
_diffrn_reflns_theta_min         2.798
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0404
_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)+(0.0428P)²+0.3741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                1687
_reflns_number_total             2142
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            rz5215sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        734.61(18)
_cod_database_code               2242188
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.955
_shelx_estimated_absorpt_t_max   0.992
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.40095(17) 0.78184(19) 0.56663(9) 0.0247(3) Uani d 1
C C2 0.34449(16) 0.59266(19) 0.59782(9) 0.0225(3) Uani d 1
C C3 0.25830(15) 0.49961(19) 0.51303(8) 0.0219(3) Uani d 1
C C4 0.18138(17) 0.3250(2) 0.49698(10) 0.0263(3) Uani d 1
H H1 0.176175 0.236360 0.546869 0.032 Uiso calc 1
C C5 0.11244(18) 0.2879(2) 0.40349(10) 0.0297(3) Uani d 1
C C6 0.11742(18) 0.4116(2) 0.32854(10) 0.0306(3) Uani d 1
H H2 0.068596 0.377653 0.266022 0.037 Uiso calc 1
C C7 0.19449(18) 0.5867(2) 0.34516(9) 0.0277(3) Uani d 1
H H3 0.199749 0.674448 0.294847 0.033 Uiso calc 1
C C8 0.26306(16) 0.62779(19) 0.43768(9) 0.0227(3) Uani d 1
F F1 0.03607(14) 0.11739(14) 0.38491(7) 0.0459(3) Uani d 1
N N1 0.34730(16) 0.79375(17) 0.47154(8) 0.0261(3) Uani d 1
N N2 0.39084(15) 0.54652(17) 0.68513(8) 0.0262(3) Uani d 1
O O1 0.48449(15) 0.90064(15) 0.61615(7) 0.0324(3) Uani d 1
O O2 0.34792(15) 0.36593(15) 0.70338(7) 0.0340(3) Uani d 1
H H4 0.384(3) 0.889(3) 0.4351(15) 0.046(5) Uiso d 1
H H5 0.409(3) 0.352(3) 0.7684(18) 0.073(7) Uiso d 1
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
O1 C1 N1 126.68(13)
O1 C1 C2 127.09(12)
N1 C1 C2 106.19(11)
N2 C2 C3 135.81(13)
N2 C2 C1 117.07(12)
C3 C2 C1 106.90(10)
C4 C3 C8 120.57(12)
C4 C3 C2 133.56(12)
C8 C3 C2 105.88(12)
C3 C4 C5 115.94(13)
C3 C4 H1 122.0
C5 C4 H1 122.0
F1 C5 C6 118.18(12)
F1 C5 C4 117.62(14)
C6 C5 C4 124.20(14)
C5 C6 C7 119.57(12)
C5 C6 H2 120.2
C7 C6 H2 120.2
C8 C7 C6 117.44(13)
C8 C7 H3 121.3
C6 C7 H3 121.3
C7 C8 C3 122.27(13)
C7 C8 N1 127.72(13)
C3 C8 N1 110.00(11)
C1 N1 C8 111.02(11)
C1 N1 H4 121.6(13)
C8 N1 H4 126.2(13)
C2 N2 O2 112.17(11)
N2 O2 H5 100.2(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.2313(16)
C1 N1 1.3599(16)
C1 C2 1.4994(19)
C2 N2 1.2857(16)
C2 C3 1.4605(17)
C3 C4 1.3883(19)
C3 C8 1.4051(18)
C4 C5 1.3898(19)
C4 H1 0.9500
C5 F1 1.3651(17)
C5 C6 1.380(2)
C6 C7 1.393(2)
C6 H2 0.9500
C7 C8 1.3825(18)
C7 H3 0.9500
C8 N1 1.4089(18)
N1 H4 0.91(2)
N2 O2 1.3674(16)
O2 H5 0.99(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H4 O1 3_676 0.91(2) 1.96(2) 2.8487(16) 164.7(18)
O2 H5 N2 2_646 0.99(3) 2.69(2) 3.2989(16) 120.2(18)
O2 H5 O1 2_646 0.99(3) 1.77(3) 2.7280(15) 163(2)
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
O1 C1 C2 N2 -1.5(2)
N1 C1 C2 N2 176.30(12)
O1 C1 C2 C3 -176.99(13)
N1 C1 C2 C3 0.84(13)
N2 C2 C3 C4 5.3(2)
C1 C2 C3 C4 179.49(13)
N2 C2 C3 C8 -174.73(14)
C1 C2 C3 C8 -0.53(13)
C8 C3 C4 C5 0.28(18)
C2 C3 C4 C5 -179.75(13)
C3 C4 C5 F1 179.86(11)
C3 C4 C5 C6 0.3(2)
F1 C5 C6 C7 -179.98(12)
C4 C5 C6 C7 -0.4(2)
C5 C6 C7 C8 -0.05(19)
C6 C7 C8 C3 0.59(19)
C6 C7 C8 N1 179.71(12)
C4 C3 C8 C7 -0.73(18)
C2 C3 C8 C7 179.29(11)
C4 C3 C8 N1 -179.98(11)
C2 C3 C8 N1 0.04(14)
O1 C1 N1 C8 177.00(13)
C2 C1 N1 C8 -0.83(14)
C7 C8 N1 C1 -178.67(12)
C3 C8 N1 C1 0.53(15)
C3 C2 N2 O2 -0.5(2)
C1 C2 N2 O2 -174.24(10)

_cod_database_fobs_code 2242188
