3,3-Difluoro-5-nitro-1<i>H</i>-indol-2(3<i>H</i>)-one: sheets of <i>R</i>~2~^2^(8) and <i>R</i>~4~^6^(34) rings built from three-centre N—H···(O)~2~ hydrogen bonds
Glidewell, Christopher; Low, John N.; Wardell, James L.; Acta Crystallographica Section C 61 (2005) o57–o59; doi:10.1107/S0108270104031026

data_2014739
_publ_section_title
;
 3,3-Difluoro-5-nitro-1<i>H</i>-indol-2(3<i>H</i>)-one: sheets of
 <i>R</i>~2~^2^(8) and <i>R</i>~4~^6^(34) rings built from three-centre
 N---H&#x00B7;&#x00B7;&#x00B7;(O)~2~ hydrogen bonds
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o57
_journal_page_last               o59
_journal_paper_doi               10.1107/S0108270104031026
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C8 H4 F2 N2 O3'
_chemical_formula_moiety         'C8 H4 F2 N2 O3'
_chemical_formula_sum            'C8 H4 F2 N2 O3'
_chemical_formula_weight         214.13
_chemical_name_systematic
;
3,3-Difluoro-5-nitro-1H-indol-2(3H)-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
_cell_angle_alpha                90.00
_cell_angle_beta                 90.951(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.0529(4)
_cell_length_b                   15.4381(6)
_cell_length_c                   9.2768(4)
_cell_measurement_reflns_used    3611
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.52
_cell_measurement_theta_min      3.13
_cell_volume                     1582.74(11)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997) and COLLECT'
_computing_data_collection       'COLLECT (Hooft, 1999)'
_computing_data_reduction        'DENZO and COLLECT'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97  and PRPKAPPA (Ferguson, 1999)'
_computing_structure_refinement  'OSCAIL and SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
'OSCAIL (McArdle , 2003) and SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            18600
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        negligible
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.241
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.7598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0902
_reflns_number_gt                2980
_reflns_number_total             3611
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk1799.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2014739
_cod_database_fobs_code          2014739