Intermolecular interactions in two (ferrocenylmethyl)benzimidazoles incorporating the 4-MeOC~6~H~4~ and 3,4-(MeO)~2~C~6~H~3~ groups: analysis of MeO—C—C distortions from ideal 120{^i̧rc} geometry
Gallagher, John F.; Hanlon, Keith; Howarth, Joshua; Acta Crystallographica Section C 57 (2001) 1410–1414; doi:10.1107/S0108270101015591

data_2012396
_publ_section_title
;
 Intermolecular interactions in two (ferrocenylmethyl)benzimidazoles
 incorporating the 4-MeOC~6~H~4~ and 3,4-(MeO)~2~C~6~H~3~ groups:
 analysis of MeO---C---C distortions from ideal 120{^\,irc} geometry
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1410
_journal_page_last               1414
_journal_paper_doi               10.1107/S0108270101015591
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          '[Fe (C5 H5) (C20 H17 N2 O)]'
_chemical_formula_moiety         'C25 H22 Fe N2 O'
_chemical_formula_structural     'C25 H22 Fe N2 O'
_chemical_formula_sum            'C25 H22 Fe N2 O'
_chemical_formula_weight         422.30
_chemical_melting_point          417
_chemical_name_systematic
;
1-Ferrocenylmethyl-2-(4-methoxyphenyl)-1H-benzimidazole
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 97.400(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4326(10)
_cell_length_b                   9.5414(7)
_cell_length_c                   17.1682(8)
_cell_measurement_reflns_used    75
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      15.6
_cell_measurement_theta_min      2.4
_cell_volume                     2019.6(2)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics
'ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 1998)'
_computing_publication_material  'SHELXL97 and PREP8 (Ferguson, 1998)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294.0(10)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .011
_diffrn_reflns_av_sigmaI/netI    .024
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6105
_diffrn_reflns_theta_full        28.0
_diffrn_reflns_theta_max         28.0
_diffrn_reflns_theta_min         2.2
_diffrn_standards_decay_%        'variation 1'
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .765
_exptl_absorpt_correction_T_max  .803
_exptl_absorpt_correction_T_min  .737
_exptl_absorpt_correction_type   \y-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          .43
_exptl_crystal_size_mid          .33
_exptl_crystal_size_min          .30
_refine_diff_density_max         .58
_refine_diff_density_min         -.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.04
_refine_ls_R_factor_all          .056
_refine_ls_R_factor_gt           .040
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.055P)^2^+0.456P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .099
_refine_ls_wR_factor_ref         .110
_reflns_number_gt                3693
_reflns_number_total             4830
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            sk1507.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2012396
_cod_database_fobs_code          2012396