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_2243457
_publ_section_title
;
 Synthesis and crystal structures of 2-(ferrocenylcarbonyl)benzoic acid
 and 3-ferrocenylphthalide
;
_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 O2)]'
_chemical_formula_moiety         'C18 H14 Fe O2'
_chemical_formula_sum            'C18 H14 Fe O2'
_chemical_formula_weight         318.14
_chemical_name_common
;
3-Ferrocenylphthalide
;
_chemical_name_systematic
;
3-Ferrocenyl-2-benzofuran-1(3<i>H</i>)-one
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.2019(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   35.4613(11)
_cell_length_b                   5.6873(2)
_cell_length_c                   13.1523(4)
_cell_measurement_reflns_used    7794
_cell_measurement_temperature    110.0(5)
_cell_measurement_theta_max      32.06
_cell_measurement_theta_min      3.15
_cell_volume                     2610.61(15)
_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 0.988
_diffrn_measured_fraction_theta_max 0.991
_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  0.0283
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_limit_h_max       52
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18463
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.096
_diffrn_reflns_theta_min         3.157
_exptl_absorpt_coefficient_mu    1.156
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause <i>et al.</i>, 2015)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.910
_refine_diff_density_min         -0.493
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         4536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.178
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0467
_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^)+(0.0315P)^2^+13.1297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                3996
_reflns_number_total             4536
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            zl2783sup1.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2243457
_shelx_estimated_absorpt_t_min   0.643
_shelx_estimated_absorpt_t_max   0.966
_shelx_hkl_checksum              2561
_shelx_res_checksum              12035
_cod_database_fobs_code 2243457