1'-Acetylferrocene-1-carboxylic acid: an instance of hydrogen bonding in the rare dimeric acid-to-ketone mode
Newman, Jacob M.; Papadakis, Markos M.; Thompson, Hugh W.; Lalancette, Roger A.; Acta Crystallographica Section C 58 (2002) m89–m91; doi:10.1107/S0108270101021771

data_2012495
_publ_section_title
;
 1'-Acetylferrocene-1-carboxylic acid: an instance of hydrogen bonding
 in the rare dimeric acid-to-ketone mode
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m89
_journal_page_last               m91
_journal_paper_doi               10.1107/S0108270101021771
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          '[Fe (C6 H5 O2) (C7 H7 O)]'
_chemical_formula_moiety         'C13 H12 Fe O3'
_chemical_formula_sum            'C13 H12 Fe O3'
_chemical_formula_weight         272.08
_chemical_melting_point          431
_chemical_name_systematic
;
1-Acetylferrocene-1'-carboxylic acid
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.290(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.331(5)
_cell_length_b                   8.769(5)
_cell_length_c                   13.616(8)
_cell_measurement_reflns_used    26
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      8.4
_cell_measurement_theta_min      2.7
_cell_volume                     1113.2(11)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       2\q/\q
_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    .066
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            2676
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        'variation <2\%'
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.345
_exptl_absorpt_correction_T_max  .92
_exptl_absorpt_correction_T_min  .68
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(SHELXTL; Sheldrick, 1997)'
_exptl_crystal_colour            red--orange
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flat plate'
_exptl_crystal_F_000             560
_exptl_crystal_size_max          .42
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .06
_refine_diff_density_max         .30
_refine_diff_density_min         -.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          .070
_refine_ls_R_factor_gt           .042
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0340P)^2^+0.3257P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .085
_refine_ls_wR_factor_ref         .095
_reflns_number_gt                1441
_reflns_number_total             1957
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fr1360.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2012495
_cod_database_fobs_code          2012495