2-{[(3-Fluorophenyl)amino]methylidene}-3-oxobutanenitrile and 5-{[(3-fluorophenyl)amino]methylidene}-2,2-dimethyl-1,3-dioxane-4,6-dione: X-ray and DFT studies
Langer, Vratislav; Mach, Pavol; Smrčok, Ľubomír; Milata, Viktor; Plevová, Kristína; Acta Crystallographica Section C 66 (2010) o392–o395; doi:10.1107/S0108270110023334

data_2017760
_publ_section_title
;
 2-{[(3-Fluorophenyl)amino]methylidene}-3-oxobutanenitrile and
 5-{[(3-fluorophenyl)amino]methylidene}-2,2-dimethyl-1,3-dioxane-4,6-dione:
 X-ray and DFT studies
;
_journal_coeditor_code           SK3374
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o392
_journal_page_last               o395
_journal_paper_doi               10.1107/S0108270110023334
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H9 F N2 O'
_chemical_formula_moiety         'C11 H9 F N2 O'
_chemical_formula_sum            'C11 H9 F N2 O'
_chemical_formula_weight         204.20
_chemical_name_systematic
;
2-{[(3-Fluorophenyl)amino]methylidene}-3-oxobutanenitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.946(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.907(2)
_cell_length_b                   5.0357(8)
_cell_length_c                   14.233(2)
_cell_measurement_reflns_used    2408
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      29.05
_cell_measurement_theta_min      2.49
_cell_volume                     942.8(2)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction
'SAINT (Bruker, 2003), SADABS (Sheldrick, 2003)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Siemens CCD area-detector'
_diffrn_measurement_method       \w
_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  0.0719
_diffrn_reflns_av_sigmaI/netI    0.0550
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13411
_diffrn_reflns_theta_full        29.26
_diffrn_reflns_theta_max         29.26
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.1626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                1650
_reflns_number_total             2554
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk3374.cif
_cod_data_source_block           I
_cod_original_cell_volume        942.8(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017760
_cod_database_fobs_code          2017760