The Knoevenagel product of indolin-2-one and ferrocene-1,1'-dicarbaldehyde
Spencer, John; Nielsen, Birthe V.; Thomas, Michael J. K.; Male, Louise; Coles, Simon J.; Acta Crystallographica Section C 67 (2011) m245–m248; doi:10.1107/S0108270111021536

data_2018145
_publ_section_title
;
 The Knoevenagel product of indolin-2-one and
 ferrocene-1,1'-dicarbaldehyde
;
_journal_coeditor_code           GG3253
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m245
_journal_page_last               m248
_journal_paper_doi               10.1107/S0108270111021536
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          '[Fe (C28 H20 N2 O2)] , 2C H2 Cl2'
_chemical_formula_moiety         'C28 H20 Fe N2 O2, 2(C H2 Cl2)'
_chemical_formula_sum            'C30 H24 Cl4 Fe N2 O2'
_chemical_formula_weight         642.16
_chemical_name_systematic
;
3,3'-[(<i>E</i>,<i>E</i>)-ferrocene-1,1'-diyldimethylidyne]diindolin-2-one
dichloromethane disolvate
;
_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                 90.0990(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.8609(2)
_cell_length_b                   14.1905(4)
_cell_length_c                   49.5413(12)
_cell_measurement_reflns_used    95670
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     5526.3(2)
_computing_cell_refinement
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)
;
_computing_molecular_graphics    'OLEX2 (Dolomanov <i>et al.</i>, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999), Mercury (Version 2.4; Macrae <i>et al.</i>,
2008) and
PARST95 (Nardelli, 1995)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 4096x4096pixels/62x62mm
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type
'Bruker Nonius APEX II CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_sigmaI/netI    0.0522
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_number            54405
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.96
_exptl_absorpt_coefficient_mu    0.965
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_correction_T_min  0.8531
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             2624
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.554
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     703
_refine_ls_number_reflns         9612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.166
_refine_ls_R_factor_all          0.1075
_refine_ls_R_factor_gt           0.0849
_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/[\s^2^(Fo^2^)+47.692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1734
_reflns_number_gt                7846
_reflns_number_total             9612
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            gg3253.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018145
_cod_database_fobs_code          2018145