#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:01:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180368 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/37/7203701.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7203701
loop_
_publ_author_name
'Petr Štěpnička'
'Ivana Císařová'
_publ_section_title
;
 Preparation and hydrogen bonding in ferrocenecarboxamides substituted
 with 2-hydroxyethyl groups at the amide nitrogen atoms
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              37
_journal_paper_doi               10.1039/b417062h
_journal_volume                  7
_journal_year                    2005
_chemical_formula_moiety         'C20 H28 Fe N2 O6'
_chemical_formula_sum            'C20 H28 Fe N2 O6'
_chemical_formula_weight         448.29
_chemical_name_common
N,N,N',N'-tetrakis(2-hydroxyethyl)-1,1'-ferrocenedicarboxamide
_chemical_name_systematic
;
N,N,N',N'-tetrakis(2-hydroxyethyl)-1,1'-ferrocenedicarboxamide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 130.317(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.3500(3)
_cell_length_b                   7.7500(4)
_cell_length_c                   15.5960(5)
_cell_measurement_reflns_used    4289
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1967.61(14)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'ω and π scans to fill the Ewald sphere'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18339
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0365
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0295P)²+2.2617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0785
_reflns_number_gt                1791
_reflns_number_total             2261
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b417062h.txt
_cod_data_source_block           ps1064
_cod_original_cell_volume        1967.6(1)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7203701
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe Fe 0.0000 0.35140(5) 0.2500 0.01639(12) Uani 1 2 d S . .
O1 O -0.02786(8) -0.07467(17) 0.35381(12) 0.0243(3) Uani 1 1 d . . .
O2 O 0.18183(9) 0.1360(2) 0.73177(12) 0.0256(3) Uani 1 1 d . . .
H91 H 0.1403(17) 0.105(4) 0.715(2) 0.049(9) Uiso 1 1 d . . .
O3 O 0.18869(9) -0.39777(19) 0.54148(14) 0.0290(4) Uani 1 1 d . . .
H92 H 0.2265(18) -0.381(4) 0.608(3) 0.061(10) Uiso 1 1 d . . .
N N 0.09563(9) 0.0346(2) 0.49660(13) 0.0192(4) Uani 1 1 d . . .
C1 C -0.01833(11) 0.2249(2) 0.34623(16) 0.0177(4) Uani 1 1 d . . .
C2 C -0.09328(11) 0.2321(3) 0.23158(16) 0.0193(4) Uani 1 1 d . . .
H2 H -0.1234 0.1374 0.1862 0.023 Uiso 1 1 calc R . .
C3 C -0.11377(12) 0.4077(3) 0.19899(18) 0.0217(4) Uani 1 1 d . . .
H3 H -0.1592 0.4479 0.1287 0.026 Uiso 1 1 calc R . .
C4 C -0.05280(12) 0.5105(3) 0.29238(17) 0.0218(4) Uani 1 1 d . . .
H4 H -0.0515 0.6305 0.2939 0.026 Uiso 1 1 calc R . .
C5 C 0.00596(12) 0.4009(2) 0.38311(17) 0.0196(4) Uani 1 1 d . . .
H5 H 0.0523 0.4364 0.4543 0.023 Uiso 1 1 calc R . .
C6 C 0.01735(11) 0.0544(2) 0.40055(16) 0.0184(4) Uani 1 1 d . . .
C7 C 0.12351(12) -0.1418(3) 0.54121(17) 0.0220(4) Uani 1 1 d . . .
H7A H 0.0780 -0.2073 0.5244 0.026 Uiso 1 1 calc R . .
H7B H 0.1664 -0.1367 0.6223 0.026 Uiso 1 1 calc R . .
C8 C 0.15613(12) -0.2329(3) 0.49114(18) 0.0249(5) Uani 1 1 d . . .
H8A H 0.1121 -0.2467 0.4108 0.030 Uiso 1 1 calc R . .
H8B H 0.1988 -0.1632 0.5027 0.030 Uiso 1 1 calc R . .
C9 C 0.15826(11) 0.1703(3) 0.55661(17) 0.0213(4) Uani 1 1 d . . .
H9A H 0.1458 0.2577 0.5030 0.026 Uiso 1 1 calc R . .
H9B H 0.2112 0.1207 0.5890 0.026 Uiso 1 1 calc R . .
C10 C 0.16458(12) 0.2559(3) 0.64938(17) 0.0246(5) Uani 1 1 d . . .
H10A H 0.2077 0.3422 0.6859 0.029 Uiso 1 1 calc R . .
H10B H 0.1133 0.3145 0.6164 0.029 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Fe C1 122.27(11) . 2 ?
C1 Fe C5 41.53(8) . . ?
C1 Fe C5 158.59(8) 2 . ?
C1 Fe C5 158.59(8) . 2 ?
C1 Fe C5 41.53(8) 2 2 ?
C5 Fe C5 158.22(11) . 2 ?
C1 Fe C2 41.26(7) . . ?
C1 Fe C2 108.32(8) 2 . ?
C5 Fe C2 68.89(8) . . ?
C5 Fe C2 122.10(8) 2 . ?
C1 Fe C2 108.32(8) . 2 ?
C1 Fe C2 41.26(7) 2 2 ?
C5 Fe C2 122.10(8) . 2 ?
C5 Fe C2 68.89(8) 2 2 ?
C2 Fe C2 126.11(11) . 2 ?
C1 Fe C4 159.82(8) . 2 ?
C1 Fe C4 69.07(8) 2 2 ?
C5 Fe C4 122.16(8) . 2 ?
C5 Fe C4 40.56(8) 2 2 ?
C2 Fe C4 156.71(8) . 2 ?
C2 Fe C4 68.11(8) 2 2 ?
C1 Fe C4 69.07(8) . . ?
C1 Fe C4 159.82(8) 2 . ?
C5 Fe C4 40.56(8) . . ?
C5 Fe C4 122.16(8) 2 . ?
C2 Fe C4 68.11(8) . . ?
C2 Fe C4 156.71(8) 2 . ?
C4 Fe C4 105.94(12) 2 . ?
C1 Fe C3 124.12(8) . 2 ?
C1 Fe C3 69.14(8) 2 2 ?
C5 Fe C3 106.70(8) . 2 ?
C5 Fe C3 68.44(8) 2 2 ?
C2 Fe C3 162.22(8) . 2 ?
C2 Fe C3 40.54(8) 2 2 ?
C4 Fe C3 40.30(8) 2 2 ?
C4 Fe C3 120.47(8) . 2 ?
C1 Fe C3 69.14(8) . . ?
C1 Fe C3 124.12(8) 2 . ?
C5 Fe C3 68.44(8) . . ?
C5 Fe C3 106.70(8) 2 . ?
C2 Fe C3 40.54(8) . . ?
C2 Fe C3 162.22(8) 2 . ?
C4 Fe C3 120.47(8) 2 . ?
C4 Fe C3 40.30(8) . . ?
C3 Fe C3 155.50(12) 2 . ?
C10 O2 H91 109(2) . . ?
C8 O3 H92 107(2) . . ?
C6 N C9 126.14(16) . . ?
C6 N C7 117.50(16) . . ?
C9 N C7 116.16(15) . . ?
C2 C1 C5 106.48(17) . . ?
C2 C1 C6 119.49(17) . . ?
C5 C1 C6 134.03(17) . . ?
C2 C1 Fe 69.71(11) . . ?
C5 C1 Fe 69.27(11) . . ?
C6 C1 Fe 125.28(13) . . ?
C3 C2 C1 108.70(17) . . ?
C3 C2 Fe 70.27(11) . . ?
C1 C2 Fe 69.04(10) . . ?
C3 C2 H2 125.7 . . ?
C1 C2 H2 125.7 . . ?
Fe C2 H2 126.6 . . ?
C4 C3 C2 107.86(17) . . ?
C4 C3 Fe 69.57(11) . . ?
C2 C3 Fe 69.18(10) . . ?
C4 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
Fe C3 H3 126.7 . . ?
C3 C4 C5 108.77(17) . . ?
C3 C4 Fe 70.12(11) . . ?
C5 C4 Fe 69.15(11) . . ?
C3 C4 H4 125.6 . . ?
C5 C4 H4 125.6 . . ?
Fe C4 H4 126.7 . . ?
C4 C5 C1 108.18(17) . . ?
C4 C5 Fe 70.29(12) . . ?
C1 C5 Fe 69.20(11) . . ?
C4 C5 H5 125.9 . . ?
C1 C5 H5 125.9 . . ?
Fe C5 H5 126.2 . . ?
O1 C6 N 119.48(18) . . ?
O1 C6 C1 117.56(16) . . ?
N C6 C1 122.96(17) . . ?
N C7 C8 111.66(17) . . ?
N C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
N C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
O3 C8 C7 110.94(17) . . ?
O3 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.0 . . ?
N C9 C10 113.85(16) . . ?
N C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
N C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
O2 C10 C9 112.69(17) . . ?
O2 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
O2 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe C1 2.0315(19) . ?
Fe C1 2.0315(19) 2 ?
Fe C5 2.033(2) . ?
Fe C5 2.033(2) 2 ?
Fe C2 2.0405(19) . ?
Fe C2 2.0405(19) 2 ?
Fe C4 2.048(2) 2 ?
Fe C4 2.048(2) . ?
Fe C3 2.0549(19) 2 ?
Fe C3 2.0549(19) . ?
O1 C6 1.246(2) . ?
O2 C10 1.428(2) . ?
O2 H91 0.78(3) . ?
O3 C8 1.423(2) . ?
O3 H92 0.81(3) . ?
N C6 1.349(2) . ?
N C9 1.467(2) . ?
N C7 1.473(2) . ?
C1 C2 1.435(3) . ?
C1 C5 1.441(3) . ?
C1 C6 1.486(3) . ?
C2 C3 1.419(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.413(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.414(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C7 C8 1.516(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.516(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
