#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/57/2205726.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2205726
loop_
_publ_author_name
'Duan, Xine'
'Zhang, Zhao'
'Huo, Fangjun'
_publ_section_title
;
 1,2-Bis(ferrocenylcarbonylthioureido)ethane chloroform disolvate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1004
_journal_page_last               m1005
_journal_paper_doi               10.1107/S1600536805012705
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Fe2 (C5 H5)2 (C16 H16 N4 O2 S2)], 2C H Cl3'
_chemical_formula_moiety         'C26 H26 Fe2 N4 O2 S2, 2C H Cl3'
_chemical_formula_sum            'C28 H28 Cl6 Fe2 N4 O2 S2'
_chemical_formula_weight         841.06
_chemical_name_common            'Bis(ferrocenoyl thioureylene)ethane'
_chemical_name_systematic
;
1,2-Bis(ferrocenylcarbonylthioureido)ethane chloroform trisolvate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.481(5)
_cell_angle_beta                 111.579(5)
_cell_angle_gamma                116.199(5)
_cell_formula_units_Z            1
_cell_length_a                   9.705(4)
_cell_length_b                   10.205(4)
_cell_length_c                   10.866(4)
_cell_measurement_reflns_used    3333513
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      25.43
_cell_measurement_theta_min      2.36
_cell_volume                     847.7(6)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2000)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2000)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean '100x100 microns'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2927
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.36
_diffrn_standards_decay_%        2.87
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.486
_exptl_absorpt_correction_T_max  0.866
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             426
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.631
_refine_diff_density_min         -0.581
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0684
_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)+(0.0632P)²+1.4465P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1591
_reflns_number_gt                2619
_reflns_number_total             2921
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6186.cif
_cod_data_source_block           I
_cod_original_cell_volume        847.6(6)
_cod_database_code               2205726
_cod_database_fobs_code          2205726
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Fe1 0.66907(9) 0.85815(8) 0.25395(7) 0.0365(3) Uani d . 1 Fe
C2 0.6976(7) 0.7286(6) 0.1210(6) 0.0471(13) Uani d . 1 C
H2 0.7476 0.7632 0.0618 0.056 Uiso calc R 1 H
C11 0.3892(6) 0.6422(6) -0.0490(5) 0.0373(11) Uani d . 1 C
C1 0.5178(6) 0.6628(6) 0.0857(5) 0.0393(12) Uani d . 1 C
Cl1 0.5229(3) 0.7298(3) 0.5776(2) 0.0957(7) Uani d . 1 Cl
Cl2 0.8113(4) 0.7106(3) 0.7599(4) 0.1353(12) Uani d . 1 Cl
C5 0.5013(6) 0.6289(6) 0.2059(5) 0.0391(12) Uani d . 1 C
H5 0.3970 0.5846 0.2135 0.047 Uiso calc R 1 H
N1 0.2178(5) 0.5665(5) -0.0748(4) 0.0392(10) Uani d . 1 N
H15 0.2000 0.5557 -0.0018 0.047 Uiso calc R 1 H
O1 0.4297(4) 0.6873(5) -0.1377(4) 0.0507(10) Uani d . 1 O
N2 0.0963(5) 0.5430(5) -0.3089(4) 0.0424(11) Uani d . 1 N
H16 0.2037 0.6080 -0.2909 0.039(14) Uiso calc R 1 H
C13 -0.0397(6) 0.4845(7) -0.4516(5) 0.0451(13) Uani d . 1 C
H13A -0.1071 0.5357 -0.4592 0.054 Uiso calc R 1 H
H13B -0.1200 0.3718 -0.4784 0.054 Uiso calc R 1 H
C14 0.6906(9) 0.7967(9) 0.7493(9) 0.079(2) Uani d . 1 C
H17 0.6360 0.7677 0.8118 0.095 Uiso calc R 1 H
Cl3 0.8232(3) 0.9985(3) 0.8082(3) 0.0992(7) Uani d . 1 Cl
C12 0.0702(6) 0.5054(6) -0.2039(5) 0.0363(11) Uani d . 1 C
C8 0.8605(8) 1.0824(7) 0.3653(7) 0.0622(17) Uani d . 1 C
H8 0.9819 1.1222 0.4070 0.075 Uiso calc R 1 H
C3 0.7876(7) 0.7333(7) 0.2589(6) 0.0507(14) Uani d . 1 C
H3 0.9082 0.7705 0.3081 0.061 Uiso calc R 1 H
C6 0.5849(9) 1.0058(7) 0.2102(8) 0.0671(18) Uani d . 1 C
H6 0.4876 0.9855 0.1276 0.081 Uiso calc R 1 H
C7 0.7564(9) 1.0692(7) 0.2291(8) 0.0667(18) Uani d . 1 C
H7 0.7941 1.0976 0.1619 0.080 Uiso calc R 1 H
S1 -0.12359(17) 0.38476(19) -0.21840(15) 0.0530(4) Uani d . 1 S
C4 0.6675(7) 0.6732(6) 0.3108(6) 0.0469(13) Uani d . 1 C
H4 0.6940 0.6639 0.4015 0.056 Uiso calc R 1 H
C9 0.7533(9) 1.0262(7) 0.4303(7) 0.0590(16) Uani d . 1 C
H9 0.7907 1.0218 0.5229 0.071 Uiso calc R 1 H
C10 0.5810(9) 0.9775(7) 0.3330(8) 0.0639(17) Uani d . 1 C
H10 0.4818 0.9342 0.3478 0.077 Uiso calc R 1 H
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 Fe1 C2 . . 41.52(19) n
C1 Fe1 C7 . . 120.7(3) n
C2 Fe1 C7 . . 107.0(3) n
C1 Fe1 C8 . . 155.5(2) n
C2 Fe1 C8 . . 119.7(3) n
C7 Fe1 C8 . . 40.4(3) n
C1 Fe1 C6 . . 108.2(3) n
C2 Fe1 C6 . . 125.8(3) n
C7 Fe1 C6 . . 40.7(3) n
C8 Fe1 C6 . . 67.9(3) n
C1 Fe1 C5 . . 41.4(2) n
C2 Fe1 C5 . . 69.2(2) n
C7 Fe1 C5 . . 157.0(3) n
C8 Fe1 C5 . . 161.4(2) n
C6 Fe1 C5 . . 122.0(3) n
C1 Fe1 C9 . . 162.2(2) n
C2 Fe1 C9 . . 155.0(2) n
C7 Fe1 C9 . . 68.4(3) n
C8 Fe1 C9 . . 40.8(3) n
C6 Fe1 C9 . . 67.8(3) n
C5 Fe1 C9 . . 124.7(2) n
C1 Fe1 C10 . . 125.0(2) n
C2 Fe1 C10 . . 162.7(3) n
C7 Fe1 C10 . . 68.8(3) n
C8 Fe1 C10 . . 68.7(3) n
C6 Fe1 C10 . . 40.4(3) n
C5 Fe1 C10 . . 107.7(2) n
C9 Fe1 C10 . . 40.7(3) n
C1 Fe1 C4 . . 68.9(2) n
C2 Fe1 C4 . . 68.3(2) n
C7 Fe1 C4 . . 161.0(3) n
C8 Fe1 C4 . . 124.5(2) n
C6 Fe1 C4 . . 156.7(3) n
C5 Fe1 C4 . . 40.5(2) n
C9 Fe1 C4 . . 107.6(2) n
C10 Fe1 C4 . . 121.2(3) n
C1 Fe1 C3 . . 68.9(2) n
C2 Fe1 C3 . . 40.5(2) n
C7 Fe1 C3 . . 124.5(3) n
C8 Fe1 C3 . . 107.0(3) n
C6 Fe1 C3 . . 162.2(3) n
C5 Fe1 C3 . . 68.3(2) n
C9 Fe1 C3 . . 120.4(3) n
C10 Fe1 C3 . . 155.6(3) n
C4 Fe1 C3 . . 40.2(2) n
C3 C2 C1 . . 108.2(5) n
C3 C2 Fe1 . . 70.8(3) n
C1 C2 Fe1 . . 69.2(3) n
C3 C2 H2 . . 125.9 n
C1 C2 H2 . . 125.9 n
Fe1 C2 H2 . . 125.7 n
O1 C11 N1 . . 121.3(5) n
O1 C11 C1 . . 121.6(4) n
N1 C11 C1 . . 117.0(4) n
C5 C1 C2 . . 106.8(4) n
C5 C1 C11 . . 130.8(4) y
C2 C1 C11 . . 122.4(5) y
C5 C1 Fe1 . . 69.6(3) n
C2 C1 Fe1 . . 69.3(3) n
C11 C1 Fe1 . . 125.2(4) n
C4 C5 C1 . . 107.9(5) n
C4 C5 Fe1 . . 70.3(3) n
C1 C5 Fe1 . . 68.9(3) n
C4 C5 H5 . . 126.0 n
C1 C5 H5 . . 126.0 n
Fe1 C5 H5 . . 126.3 n
C11 N1 C12 . . 127.1(4) n
C11 N1 H15 . . 116.5 n
C12 N1 H15 . . 116.5 n
C12 N2 C13 . . 124.4(4) n
C12 N2 H16 . . 117.8 n
C13 N2 H16 . . 117.8 n
N2 C13 C13 . 2_564 109.5(5) n
N2 C13 H13A . . 109.8 n
C13 C13 H13A 2_564 . 109.8 n
N2 C13 H13B . . 109.8 n
C13 C13 H13B 2_564 . 109.8 n
H13A C13 H13B . . 108.2 n
Cl2 C14 Cl3 . . 111.0(4) n
Cl2 C14 Cl1 . . 111.3(5) n
Cl3 C14 Cl1 . . 110.5(4) n
Cl2 C14 H17 . . 108.0 n
Cl3 C14 H17 . . 108.0 n
Cl1 C14 H17 . . 108.0 n
N2 C12 N1 . . 116.5(4) n
N2 C12 S1 . . 124.4(4) n
N1 C12 S1 . . 119.0(4) n
C7 C8 C9 . . 108.3(6) n
C7 C8 Fe1 . . 69.8(3) n
C9 C8 Fe1 . . 69.8(3) n
C7 C8 H8 . . 125.9 n
C9 C8 H8 . . 125.9 n
Fe1 C8 H8 . . 126.1 n
C4 C3 C2 . . 108.2(5) n
C4 C3 Fe1 . . 69.7(3) n
C2 C3 Fe1 . . 68.7(3) n
C4 C3 H3 . . 125.9 n
C2 C3 H3 . . 125.9 n
Fe1 C3 H3 . . 127.3 n
C10 C6 C7 . . 109.3(6) n
C10 C6 Fe1 . . 70.3(3) n
C7 C6 Fe1 . . 69.5(4) n
C10 C6 H6 . . 125.3 n
C7 C6 H6 . . 125.3 n
Fe1 C6 H6 . . 126.4 n
C8 C7 C6 . . 107.4(6) n
C8 C7 Fe1 . . 69.8(3) n
C6 C7 Fe1 . . 69.7(3) n
C8 C7 H7 . . 126.3 n
C6 C7 H7 . . 126.3 n
Fe1 C7 H7 . . 125.7 n
C3 C4 C5 . . 108.8(5) n
C3 C4 Fe1 . . 70.1(3) n
C5 C4 Fe1 . . 69.2(3) n
C3 C4 H4 . . 125.6 n
C5 C4 H4 . . 125.6 n
Fe1 C4 H4 . . 126.6 n
C10 C9 C8 . . 108.2(6) n
C10 C9 Fe1 . . 69.9(3) n
C8 C9 Fe1 . . 69.3(3) n
C10 C9 H9 . . 125.9 n
C8 C9 H9 . . 125.9 n
Fe1 C9 H9 . . 126.4 n
C6 C10 C9 . . 106.8(6) n
C6 C10 Fe1 . . 69.3(4) n
C9 C10 Fe1 . . 69.4(3) n
C6 C10 H10 . . 126.6 n
C9 C10 H10 . . 126.6 n
Fe1 C10 H10 . . 126.3 n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Fe1 C1 . 2.023(5) n
Fe1 C2 . 2.024(5) n
Fe1 C7 . 2.029(6) n
Fe1 C8 . 2.030(6) n
Fe1 C6 . 2.031(6) n
Fe1 C5 . 2.033(5) n
Fe1 C9 . 2.036(6) n
Fe1 C10 . 2.044(6) n
Fe1 C4 . 2.047(5) n
Fe1 C3 . 2.053(5) n
C2 C3 . 1.412(8) n
C2 C1 . 1.435(7) n
C2 H2 . 0.9500 n
C11 O1 . 1.231(6) n
C11 N1 . 1.384(6) n
C11 C1 . 1.448(7) n
C1 C5 . 1.434(7) n
Cl1 C14 . 1.758(8) n
Cl2 C14 . 1.729(8) n
C5 C4 . 1.412(7) n
C5 H5 . 0.9500 n
N1 C12 . 1.394(6) n
N1 H15 . 0.8800 n
N2 C12 . 1.318(6) n
N2 C13 . 1.447(6) n
N2 H16 . 0.8800 ?
C13 C13 2_564 1.502(10) n
C13 H13A . 0.9900 n
C13 H13B . 0.9900 n
C14 Cl3 . 1.751(8) n
C14 H17 . 1.0000 n
C12 S1 . 1.665(5) n
C8 C7 . 1.401(9) n
C8 C9 . 1.419(9) n
C8 H8 . 0.9500 n
C3 C4 . 1.408(8) n
C3 H3 . 0.9500 n
C6 C10 . 1.407(10) n
C6 C7 . 1.413(9) n
C6 H6 . 0.9500 n
C7 H7 . 0.9500 n
C4 H4 . 0.9500 n
C9 C10 . 1.418(9) n
C9 H9 . 0.9500 n
C10 H10 . 0.9500 n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H16 O1 . 0.88 1.92 2.616(5) 135 y
N1 H15 S1 2_565 0.88 2.83 3.663(4) 158 y
C5 H5 S1 2_565 0.95 2.82 3.660(5) 147 y
C14 H17 O1 1_556 1.00 2.11 3.044(7) 155 y
