Synthesis and crystal structures of 2-(ferrocenylcarbonyl)benzoic acid and 3-ferrocenylphthalide
Pokharel, Uttam R.; Bergeron, Jonathan T.; Fronczek, Frank R.; Acta Crystallographica Section E 76 (2020) 1163–1167; doi:10.1107/S2056989020008452

data_2243456
_publ_section_title
;
 Synthesis and crystal structures of 2-(ferrocenylcarbonyl)benzoic acid
 and 3-ferrocenylphthalide
;
_journal_coeditor_code           ZL2783
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1163
_journal_page_last               1167
_journal_paper_doi               10.1107/S2056989020008452
_journal_volume                  76
_journal_year                    2020
_chemical_formula_iupac          '[Fe (C5 H5) (C13 H9 O3)]'
_chemical_formula_moiety         'C18 H14 Fe O3'
_chemical_formula_sum            'C18 H14 Fe O3'
_chemical_formula_weight         334.14
_chemical_name_systematic
;
2-(Ferrocenylcarbonyl)benzoic acid
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.758(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.1332(13)
_cell_length_b                   7.4478(5)
_cell_length_c                   11.0345(8)
_cell_measurement_reflns_used    7843
_cell_measurement_temperature    110.0(5)
_cell_measurement_theta_max      31.99
_cell_measurement_theta_min      2.47
_cell_volume                     1355.14(17)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>, 2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2014/7</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      110.0(5)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25434
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.109
_diffrn_reflns_theta_min         1.235
_exptl_absorpt_coefficient_mu    1.123
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4737
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0391P)^2^+0.6785P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                3834
_reflns_number_total             4737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zl2783sup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        1355.13(17)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2243456
_shelx_estimated_absorpt_t_min   0.767
_shelx_estimated_absorpt_t_max   0.946
_shelx_hkl_checksum              96540
_shelx_res_checksum              79492
_cod_database_fobs_code 2243456