#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/02/2230215.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_2230215
loop_
_publ_author_name
'Wei, Wen-Bin'
'Tian, Shuo'
'Shen, Hong'
'Sun, Jie'
'Wang, Hai-Bo'
_publ_section_title
;
 5-Fluoro-3-(2-phenylhydrazinylidene)indolin-2-one
;
_journal_coeditor_code           AA2004
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1294
_journal_paper_doi               10.1107/S1600536811015285
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H10 F N3 O'
_chemical_formula_moiety         'C14 H10 F N3 O'
_chemical_formula_sum            'C14 H10 F N3 O'
_chemical_formula_weight         255.25
_chemical_melting_point          543
_chemical_name_systematic
;
5-Fluoro-3-(2-phenylhydrazinylidene)indolin-2-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                69.98(3)
_cell_angle_beta                 75.43(3)
_cell_angle_gamma                88.33(3)
_cell_formula_units_Z            2
_cell_length_a                   6.4840(13)
_cell_length_b                   8.7250(17)
_cell_length_c                   11.672(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      10
_cell_volume                     599.3(2)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_reduction        'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2413
_diffrn_reflns_theta_full        25.38
_diffrn_reflns_theta_max         25.38
_diffrn_reflns_theta_min         1.92
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  7200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.9696
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.199
_refine_ls_extinction_coef       0.058(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2202
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.1080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1533
_reflns_number_gt                1767
_reflns_number_total             2202
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            aa2004.cif
_cod_data_source_block           I
_cod_database_code               2230215
_cod_database_fobs_code          2230215
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.3760(2) 0.63511(17) 1.06116(14) 0.0569(4) Uani d . 1 1 . .
F F1 0.5373(2) 0.7060(2) 0.55092(14) 0.0974(6) Uani d . 1 1 . .
N N1 -0.2569(2) 0.5813(2) 0.87432(15) 0.0520(4) Uani d . 1 1 . .
H H1A -0.3724 0.5353 0.8743 0.062 Uiso calc R 1 1 . .
C C1 -0.2376(3) 0.6408(2) 0.96456(18) 0.0462(5) Uani d . 1 1 . .
N N2 0.0754(2) 0.77749(18) 0.98762(14) 0.0453(4) Uani d . 1 1 . .
C C2 -0.0150(3) 0.7110(2) 0.92643(17) 0.0438(4) Uani d . 1 1 . .
N N3 -0.0413(2) 0.78890(19) 1.09465(15) 0.0494(4) Uani d . 1 1 . .
H H3A -0.1751 0.7592 1.1191 0.059 Uiso calc R 1 1 . .
C C3 0.2929(3) 0.7207(2) 0.73265(18) 0.0539(5) Uani d . 1 1 . .
H H3B 0.3971 0.7736 0.7502 0.065 Uiso calc R 1 1 . .
C C4 0.3360(3) 0.6740(3) 0.6286(2) 0.0634(6) Uani d . 1 1 . .
C C5 0.1875(4) 0.5940(3) 0.5986(2) 0.0671(6) Uani d . 1 1 . .
H H5A 0.2252 0.5640 0.5273 0.081 Uiso calc R 1 1 . .
C C6 -0.0170(4) 0.5592(3) 0.6761(2) 0.0587(5) Uani d . 1 1 . .
H H6A -0.1202 0.5065 0.6576 0.070 Uiso calc R 1 1 . .
C C7 -0.0645(3) 0.6043(2) 0.78105(18) 0.0472(5) Uani d . 1 1 . .
C C8 0.0879(3) 0.6855(2) 0.81030(17) 0.0451(5) Uani d . 1 1 . .
C C9 0.0503(3) 0.8486(2) 1.16853(17) 0.0451(5) Uani d . 1 1 . .
C C10 0.2649(3) 0.8988(2) 1.13266(19) 0.0529(5) Uani d . 1 1 . .
H H10A 0.3526 0.8928 1.0580 0.063 Uiso calc R 1 1 . .
C C11 0.3471(4) 0.9576(3) 1.2088(2) 0.0632(6) Uani d . 1 1 . .
H H11A 0.4906 0.9929 1.1841 0.076 Uiso calc R 1 1 . .
C C12 0.2208(4) 0.9652(3) 1.3206(2) 0.0662(6) Uani d . 1 1 . .
H H12A 0.2783 1.0050 1.3711 0.079 Uiso calc R 1 1 . .
C C13 0.0094(4) 0.9132(3) 1.3566(2) 0.0658(6) Uani d . 1 1 . .
H H13A -0.0764 0.9169 1.4324 0.079 Uiso calc R 1 1 . .
C C14 -0.0778(3) 0.8555(2) 1.28156(19) 0.0555(5) Uani d . 1 1 . .
H H14A -0.2218 0.8213 1.3066 0.067 Uiso calc R 1 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'
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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C7 . . 111.36(15) ?
C1 N1 H1A . . 124.3 ?
C7 N1 H1A . . 124.3 ?
O1 C1 N1 . . 127.23(16) ?
O1 C1 C2 . . 126.46(17) ?
N1 C1 C2 . . 106.29(16) ?
C2 N2 N3 . . 118.21(15) ?
N2 C2 C8 . . 125.87(16) ?
N2 C2 C1 . . 127.33(17) ?
C8 C2 C1 . . 106.74(15) ?
N2 N3 C9 . . 120.78(15) ?
N2 N3 H3A . . 119.6 ?
C9 N3 H3A . . 119.6 ?
C4 C3 C8 . . 117.08(19) ?
C4 C3 H3B . . 121.5 ?
C8 C3 H3B . . 121.5 ?
F1 C4 C3 . . 118.3(2) ?
F1 C4 C5 . . 117.90(19) ?
C3 C4 C5 . . 123.8(2) ?
C6 C5 C4 . . 119.1(2) ?
C6 C5 H5A . . 120.5 ?
C4 C5 H5A . . 120.5 ?
C7 C6 C5 . . 118.42(19) ?
C7 C6 H6A . . 120.8 ?
C5 C6 H6A . . 120.8 ?
C6 C7 N1 . . 129.42(18) ?
C6 C7 C8 . . 121.89(19) ?
N1 C7 C8 . . 108.69(16) ?
C3 C8 C7 . . 119.75(18) ?
C3 C8 C2 . . 133.33(17) ?
C7 C8 C2 . . 106.90(16) ?
C10 C9 C14 . . 119.59(18) ?
C10 C9 N3 . . 121.66(17) ?
C14 C9 N3 . . 118.75(17) ?
C11 C10 C9 . . 119.34(19) ?
C11 C10 H10A . . 120.3 ?
C9 C10 H10A . . 120.3 ?
C12 C11 C10 . . 121.3(2) ?
C12 C11 H11A . . 119.4 ?
C10 C11 H11A . . 119.4 ?
C13 C12 C11 . . 119.2(2) ?
C13 C12 H12A . . 120.4 ?
C11 C12 H12A . . 120.4 ?
C12 C13 C14 . . 120.8(2) ?
C12 C13 H13A . . 119.6 ?
C14 C13 H13A . . 119.6 ?
C13 C14 C9 . . 119.79(19) ?
C13 C14 H14A . . 120.1 ?
C9 C14 H14A . . 120.1 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.239(2) ?
F1 C4 . 1.363(2) ?
N1 C1 . 1.356(2) ?
N1 C7 . 1.401(2) ?
N1 H1A . 0.8600 ?
C1 C2 . 1.483(2) ?
N2 C2 . 1.306(2) ?
N2 N3 . 1.322(2) ?
C2 C8 . 1.441(3) ?
N3 C9 . 1.396(2) ?
N3 H3A . 0.8600 ?
C3 C4 . 1.371(3) ?
C3 C8 . 1.382(3) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.382(3) ?
C5 C6 . 1.378(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.373(3) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.404(2) ?
C9 C10 . 1.386(3) ?
C9 C14 . 1.391(3) ?
C10 C11 . 1.380(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.377(3) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.370(3) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.382(3) ?
C13 H13A . 0.9300 ?
C14 H14A . 0.9300 ?
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 H1A O1 2_467 0.86 2.05 2.861(2) 157
N3 H3A O1 . 0.86 2.09 2.760(2) 135
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C1 O1 . . . . -177.71(18) ?
C7 N1 C1 C2 . . . . 0.9(2) ?
N3 N2 C2 C8 . . . . -178.66(16) ?
N3 N2 C2 C1 . . . . -1.7(3) ?
O1 C1 C2 N2 . . . . 0.7(3) ?
N1 C1 C2 N2 . . . . -177.91(17) ?
O1 C1 C2 C8 . . . . 178.17(18) ?
N1 C1 C2 C8 . . . . -0.5(2) ?
C2 N2 N3 C9 . . . . 175.62(16) ?
C8 C3 C4 F1 . . . . -179.48(19) ?
C8 C3 C4 C5 . . . . -0.5(3) ?
F1 C4 C5 C6 . . . . 179.6(2) ?
C3 C4 C5 C6 . . . . 0.6(4) ?
C4 C5 C6 C7 . . . . -0.7(3) ?
C5 C6 C7 N1 . . . . -179.05(19) ?
C5 C6 C7 C8 . . . . 0.7(3) ?
C1 N1 C7 C6 . . . . 178.71(19) ?
C1 N1 C7 C8 . . . . -1.0(2) ?
C4 C3 C8 C7 . . . . 0.4(3) ?
C4 C3 C8 C2 . . . . 178.50(19) ?
C6 C7 C8 C3 . . . . -0.6(3) ?
N1 C7 C8 C3 . . . . 179.20(16) ?
C6 C7 C8 C2 . . . . -179.09(17) ?
N1 C7 C8 C2 . . . . 0.7(2) ?
N2 C2 C8 C3 . . . . -0.9(3) ?
C1 C2 C8 C3 . . . . -178.4(2) ?
N2 C2 C8 C7 . . . . 177.35(17) ?
C1 C2 C8 C7 . . . . -0.1(2) ?
N2 N3 C9 C10 . . . . 0.4(3) ?
N2 N3 C9 C14 . . . . -178.79(16) ?
C14 C9 C10 C11 . . . . -1.2(3) ?
N3 C9 C10 C11 . . . . 179.65(17) ?
C9 C10 C11 C12 . . . . 1.0(3) ?
C10 C11 C12 C13 . . . . -0.1(4) ?
C11 C12 C13 C14 . . . . -0.7(4) ?
C12 C13 C14 C9 . . . . 0.5(3) ?
C10 C9 C14 C13 . . . . 0.4(3) ?
N3 C9 C14 C13 . . . . 179.65(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4643639
