#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/06/2220619.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_2220619
loop_
_publ_author_name
'Zhang, Hongming'
'Ankati, Haribabu'
'Akubathini, Shashidhar Kumar'
'Biehl, Ed'
_publ_section_title
;
 (Z)-5-Fluoro-3-[(1H-pyrrol-2-yl)methylene]indolin-2-one
;
_journal_coeditor_code           SI2132
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o8
_journal_paper_doi               10.1107/S1600536808040178
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H9 F N2 O'
_chemical_formula_moiety         'C13 H9 F N2 O'
_chemical_formula_sum            'C13 H9 F N2 O'
_chemical_formula_weight         228.22
_chemical_name_systematic
;
(Z)-5-Fluoro-3-[(1H-pyrrol-2-yl)methylene]indolin-2-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.3900(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6093(5)
_cell_length_b                   6.1270(4)
_cell_length_c                   22.8912(16)
_cell_measurement_reflns_used    3595
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.67
_cell_volume                     1066.92(12)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'Bruker APEX'
_diffrn_measurement_method       'φ and ω'
_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  0.022
_diffrn_reflns_av_sigmaI/netI    0.017
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12282
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plates
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2552
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.054
_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)+(0.0587P)²+0.3105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.131
_refine_ls_wR_factor_ref         0.137
_reflns_number_gt                2167
_reflns_number_total             2552
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            si2132.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220619
_cod_database_fobs_code          2220619
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.36941(18) 0.7704(2) -0.02026(6) 0.0462(3) Uani d . 1 . .
H H1 0.4156 0.8783 -0.0384 0.055 Uiso calc R 1 . .
C C2 0.3608(2) 0.7558(3) 0.03865(7) 0.0422(4) Uani d . 1 . .
O O2 0.41973(16) 0.89761(19) 0.07266(5) 0.0515(3) Uani d . 1 . .
C C3 0.27094(19) 0.5468(2) 0.05187(7) 0.0395(3) Uani d . 1 . .
C C4 0.1488(2) 0.2559(3) -0.02156(7) 0.0457(4) Uani d . 1 . .
H H4 0.1059 0.1591 0.0060 0.055 Uiso calc R 1 . .
C C5 0.1325(2) 0.2144(3) -0.08055(8) 0.0503(4) Uani d . 1 . .
F F5 0.04936(17) 0.0275(2) -0.09798(5) 0.0727(4) Uani d . 1 . .
C C6 0.1934(2) 0.3515(3) -0.12313(7) 0.0536(4) Uani d . 1 . .
H H6 0.1788 0.3157 -0.1624 0.064 Uiso calc R 1 . .
C C7 0.2772(2) 0.5443(3) -0.10659(7) 0.0511(4) Uani d . 1 . .
H H7 0.3204 0.6399 -0.1343 0.061 Uiso calc R 1 . .
C C8 0.2942(2) 0.5888(3) -0.04789(7) 0.0421(4) Uani d . 1 . .
C C9 0.23179(19) 0.4481(2) -0.00504(6) 0.0395(3) Uani d . 1 . .
C C10 0.2305(2) 0.4604(3) 0.10429(7) 0.0448(4) Uani d . 1 . .
H H10 0.1771 0.3241 0.1019 0.054 Uiso calc R 1 . .
N N11 0.3347(2) 0.7320(3) 0.17745(6) 0.0587(4) Uani d . 1 . .
H H11 0.3819 0.8215 0.1535 0.070 Uiso calc R 1 . .
C C12 0.2548(2) 0.5398(3) 0.16222(7) 0.0488(4) Uani d . 1 . .
C C13 0.1974(3) 0.4470(4) 0.21346(8) 0.0667(6) Uani d . 1 . .
H H13 0.1390 0.3144 0.2167 0.080 Uiso calc R 1 . .
C C14 0.2423(4) 0.5862(4) 0.25906(9) 0.0792(7) Uani d . 1 . .
H H14 0.2184 0.5654 0.2983 0.095 Uiso calc R 1 . .
C C15 0.3282(4) 0.7598(4) 0.23562(9) 0.0756(7) Uani d . 1 . .
H H15 0.3746 0.8777 0.2564 0.091 Uiso calc R 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
C2 N1 C8 . . 111.66(13) ?
C2 N1 H1 . . 124.2 ?
C8 N1 H1 . . 124.2 ?
O2 C2 N1 . . 123.50(14) ?
O2 C2 C3 . . 129.46(14) ?
N1 C2 C3 . . 107.04(14) ?
C10 C3 C9 . . 125.66(15) ?
C10 C3 C2 . . 129.26(15) ?
C9 C3 C2 . . 105.08(13) ?
C5 C4 C9 . . 117.01(15) ?
C5 C4 H4 . . 121.5 ?
C9 C4 H4 . . 121.5 ?
F5 C5 C6 . . 117.86(15) ?
F5 C5 C4 . . 118.16(16) ?
C6 C5 C4 . . 123.97(16) ?
C5 C6 C7 . . 119.06(15) ?
C5 C6 H6 . . 120.5 ?
C7 C6 H6 . . 120.5 ?
C8 C7 C6 . . 117.81(15) ?
C8 C7 H7 . . 121.1 ?
C6 C7 H7 . . 121.1 ?
C7 C8 N1 . . 128.97(15) ?
C7 C8 C9 . . 122.58(15) ?
N1 C8 C9 . . 108.45(14) ?
C4 C9 C8 . . 119.57(14) ?
C4 C9 C3 . . 132.66(14) ?
C8 C9 C3 . . 107.77(14) ?
C3 C10 C12 . . 131.79(16) ?
C3 C10 H10 . . 114.1 ?
C12 C10 H10 . . 114.1 ?
C15 N11 C12 . . 109.57(16) ?
C15 N11 H11 . . 125.2 ?
C12 N11 H11 . . 125.2 ?
N11 C12 C13 . . 106.60(16) ?
N11 C12 C10 . . 125.47(15) ?
C13 C12 C10 . . 127.88(17) ?
C12 C13 C14 . . 107.97(19) ?
C12 C13 H13 . . 126.0 ?
C14 C13 H13 . . 126.0 ?
C15 C14 C13 . . 107.19(18) ?
C15 C14 H14 . . 126.4 ?
C13 C14 H14 . . 126.4 ?
N11 C15 C14 . . 108.66(19) ?
N11 C15 H15 . . 125.7 ?
C14 C15 H15 . . 125.7 ?
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
N1 C2 . 1.355(2) ?
N1 C8 . 1.396(2) ?
N1 H1 . 0.8600 ?
C2 O2 . 1.2429(19) ?
C2 C3 . 1.486(2) ?
C3 C10 . 1.354(2) ?
C3 C9 . 1.460(2) ?
C4 C5 . 1.377(2) ?
C4 C9 . 1.385(2) ?
C4 H4 . 0.9300 ?
C5 F5 . 1.364(2) ?
C5 C6 . 1.376(3) ?
C6 C7 . 1.390(3) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.374(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.397(2) ?
C10 C12 . 1.421(2) ?
C10 H10 . 0.9300 ?
N11 C15 . 1.344(2) ?
N11 C12 . 1.367(2) ?
N11 H11 . 0.8600 ?
C12 C13 . 1.384(2) ?
C13 C14 . 1.385(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.365(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 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 H1 O2 3_675 0.86 2.03 2.8711(17) 165.9
N11 H11 O2 . 0.86 1.94 2.6977(19) 146.8
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741305
