#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/13/2011368.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_2011368
loop_
_publ_author_name
'Naumov, Pance'
'Anastasova, Frosa'
'Drew, Michael G. B.'
'Ng, Seik Weng'
_publ_section_title
;
 5-Fluoroindoline-2,3-dione
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              e406
_journal_page_last               e407
_journal_paper_doi               10.1107/S0108270100010568
_journal_volume                  56
_journal_year                    2000
_chemical_formula_moiety         'C8 H4 F N O2'
_chemical_formula_sum            'C8 H4 F N O2'
_chemical_formula_weight         165.12
_chemical_name_systematic
;
 5-Fluoro-2,3-indolinedione
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.410(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.789(7)
_cell_length_b                   12.200(10)
_cell_length_c                   14.99(2)
_cell_measurement_reflns_used    2310
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.97
_cell_measurement_theta_min      2.15
_cell_volume                     690.9(17)
_computing_cell_refinement       XDS
_computing_data_collection       'XDS (Kabsch, 1988)'
_computing_data_reduction        XDS
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full .930
_diffrn_measured_fraction_theta_max .930
_diffrn_measurement_device_type  'MarResearch Image Plate'
_diffrn_measurement_method
'Method: 95 frames at 2° intervals, counting time 2 min.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .034
_diffrn_reflns_av_sigmaI/netI    .0396
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2310
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    .134
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Parallelepiped
_exptl_crystal_F_000             336
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .25
_refine_diff_density_max         .20
_refine_diff_density_min         -.19
_refine_ls_extinction_coef       .040(10)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          .088
_refine_ls_R_factor_gt           .053
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0891P)²+0.1412P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .166
_reflns_number_gt                851
_reflns_number_total             1265
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qd0008.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        691(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2011368
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_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
_atom_site_type_symbol
F1 .3855(6) 1.0281(2) .26140(10) .0844(7) Uani d . 1 . . F
O1 .9244(6) .8277(2) .57240(10) .0685(7) Uani d . 1 . . O
O2 .7484(6) .5926(2) .57590(10) .0708(7) Uani d . 1 . . O
N1 .4707(6) .6339(2) .43710(10) .0537(7) Uani d . 1 . . N
C1 .4261(7) .7294(2) .3836(2) .0443(7) Uani d . 1 . . C
C2 .2582(7) .7380(2) .2989(2) .0511(7) Uani d . 1 . . C
C3 .2485(7) .8403(3) .2589(2) .0541(7) Uani d . 1 . . C
C4 .4036(8) .9289(2) .3041(2) .0549(8) Uani d . 1 . . C
C5 .5729(7) .9227(2) .3879(2) .0524(7) Uani d . 1 . . C
C6 .5829(6) .8200(2) .4278(2) .0431(7) Uani d . 1 . . C
C7 .7472(7) .7809(2) .5134(2) .0477(7) Uani d . 1 . . C
C8 .6606(8) .6565(2) .5154(2) .0530(7) Uani d . 1 . . C
H1 .3885 .5703 .4220 .064 Uiso calc R 1 . . H
H2 .1552 .6773 .2698 .061 Uiso calc R 1 . . H
H3 .1381 .8495 .2018 .065 Uiso calc R 1 . . H
H5 .6753 .9838 .4165 .063 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
F1 .115(2) .0610(10) .0760(10) -.0010(10) -.0020(10) .0240(10)
O1 .084(2) .0690(10) .0500(10) -.0150(10) -.0150(10) -.0090(10)
O2 .099(2) .0610(10) .0480(10) -.0120(10) -.0210(10) .0100(10)
N1 .072(2) .0430(10) .0440(10) -.0080(10) -.0110(10) .0010(10)
C1 .050(2) .045(2) .0380(10) -.0040(10) .0030(10) -.0020(10)
C2 .056(2) .054(2) .042(2) -.0010(10) -.0030(10) -.0070(10)
C3 .058(2) .066(2) .0370(10) .0060(10) .0000(10) .0020(10)
C4 .067(2) .048(2) .051(2) .0070(10) .0090(10) .0120(10)
C5 .060(2) .048(2) .050(2) -.0030(10) .0090(10) -.0020(10)
C6 .0470(10) .0430(10) .0390(10) -.0030(10) .0030(10) -.0030(10)
C7 .052(2) .051(2) .0400(10) -.0040(10) -.0010(10) -.0050(10)
C8 .062(2) .057(2) .0390(10) -.0070(10) -.0050(10) .0020(10)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F .0171 .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
C8 N1 C1 110.8(2)
C2 C1 C6 121.7(3)
C2 C1 N1 127.6(2)
C6 C1 N1 110.7(2)
C1 C2 C3 117.5(3)
C2 C3 C4 119.8(3)
C5 C4 F1 118.8(3)
C5 C4 C3 124.0(3)
F1 C4 C3 117.3(3)
C4 C5 C6 116.2(3)
C5 C6 C1 120.9(2)
C5 C6 C7 131.9(2)
C1 C6 C7 107.1(2)
O1 C7 C6 131.4(3)
O1 C7 C8 123.6(2)
C6 C7 C8 105.0(2)
O2 C8 N1 127.5(3)
O2 C8 C7 126.2(2)
N1 C8 C7 106.3(2)
C8 N1 H1 124.6
C1 C2 H2 121.2
C3 C2 H2 121.2
C4 C3 H3 120.1
C2 C3 H3 120.1
C4 C5 H5 121.9
C6 C5 H5 121.9
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
F1 C4 . 1.368(3) ?
O1 C7 . 1.211(3) ?
O2 C8 . 1.222(3) ?
N1 C1 . 1.417(3) ?
N1 C8 . 1.356(4) ?
C1 C2 . 1.378(4) ?
C1 C6 . 1.398(4) ?
C2 C3 . 1.385(4) ?
C3 C4 . 1.382(4) ?
C4 C5 . 1.368(4) ?
C5 C6 . 1.388(4) ?
C6 C7 . 1.463(4) ?
C7 C8 . 1.554(4) ?
N1 H1 . .8600 ?
C2 H2 . .9300 ?
C3 H3 . .9300 ?
C5 H5 . .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
_geom_hbond_publ_flag
N1 H1 O2 3_666 .86 2.06 2.888(4) 162.8 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 206493
