#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2009135.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_2009135
loop_
_publ_author_name
'Xiao, W.'
'Lu, Z.-L.'
'Li, R.-Y.'
'Su, C.-Y.'
'Kang, B.-S.'
'Shanmuga Sundara Raj, S.'
'Fun, H.-K.'
_publ_section_title
;
 1,1'-Diacetylferrocene bis(thiosemicarbazone) monohydrate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1762
_journal_page_last               1764
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          '[Fe (C8 H10 N3 S)2] , H2 O'
_chemical_formula_sum            'C16 H22 Fe N6 O S2'
_chemical_formula_weight         434.37
_chemical_name_systematic
;
1,1'-Diacetylferrocene bis(thiosemicarbazone) monohydrate
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 125.9780(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.0676(2)
_cell_length_b                   8.80130(10)
_cell_length_c                   18.44700(10)
_cell_measurement_reflns_used    8192
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.19
_cell_measurement_theta_min      2.73
_cell_volume                     3819.10(7)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PARST (Nardelli, 1995)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Siemens SMART CCD area detector'
_diffrn_measurement_method       '\w scan'
_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  0.023
_diffrn_reflns_av_sigmaI/netI    0.033
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            16834
_diffrn_reflns_theta_full        33.15
_diffrn_reflns_theta_max         33.15
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    1.027
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.563
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         7072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[\s^2^(Fo^2^)+(0.0290P)^2^+3.2041P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.092
_reflns_number_gt                5528
_reflns_number_total             7072
_reflns_threshold_expression     'I > 2\s(I)'
_[local]_cod_data_source_file    ha1259.cif
_[local]_cod_data_source_block   I
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
_cod_original_cell_volume        3819.09(5)
_cod_database_code               2009135
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_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_occupancy
_atom_site_type_symbol
Fe1 0.137062(9) 0.46447(3) 0.366253(15) 0.03011(6) Uani d 1 Fe
S1 0.00288(2) -0.20160(6) 0.45250(4) 0.05009(13) Uani d 1 S
S2 0.175394(17) 0.07205(5) 0.75890(3) 0.03835(10) Uani d 1 S
N1 0.06817(5) 0.08200(15) 0.37101(9) 0.0314(3) Uani d 1 N
N2 0.06260(6) -0.02165(16) 0.42170(9) 0.0348(3) Uani d 1 N
N3 -0.03391(6) -0.0130(2) 0.31818(11) 0.0484(4) Uani d 1 N
N4 0.15776(6) 0.37979(17) 0.59024(9) 0.0373(3) Uani d 1 N
N5 0.14449(6) 0.27609(18) 0.63203(9) 0.0374(3) Uani d 1 N
N6 0.23890(7) 0.2743(3) 0.74717(13) 0.0525(4) Uani d 1 N
C1 0.07853(7) 0.3177(2) 0.27065(11) 0.0404(4) Uani d 1 C
C2 0.10193(10) 0.4085(3) 0.23570(13) 0.0507(5) Uani d 1 C
C3 0.16126(10) 0.3834(3) 0.28898(15) 0.0522(5) Uani d 1 C
C4 0.17528(8) 0.2772(2) 0.35661(14) 0.0423(4) Uani d 1 C
C5 0.12379(6) 0.23335(19) 0.34568(11) 0.0335(3) Uani d 1 C
C6 0.11906(6) 0.12392(17) 0.40093(10) 0.0310(3) Uani d 1 C
C7 0.17228(8) 0.0661(3) 0.48559(15) 0.0461(4) Uani d 1 C
C8 0.01032(6) -0.07049(18) 0.39339(11) 0.0327(3) Uani d 1 C
C9 0.09374(8) 0.6183(2) 0.38842(13) 0.0418(4) Uani d 1 C
C10 0.12591(10) 0.6944(2) 0.36373(15) 0.0477(4) Uani d 1 C
C11 0.18403(9) 0.6573(2) 0.42706(14) 0.0459(4) Uani d 1 C
C12 0.18873(8) 0.5580(2) 0.49199(12) 0.0388(4) Uani d 1 C
C13 0.13251(7) 0.53338(18) 0.46837(11) 0.0333(3) Uani d 1 C
C14 0.11669(7) 0.43278(18) 0.51381(11) 0.0327(3) Uani d 1 C
C15 0.05501(8) 0.3978(3) 0.46773(15) 0.0472(4) Uani d 1 C
C16 0.18749(6) 0.21608(19) 0.71077(10) 0.0340(3) Uani d 1 C
O1W 0.14081(8) -0.1773(2) 0.59997(11) 0.0610(4) Uani d 1 O
H12 0.2246(10) 0.514(3) 0.5446(16) 0.054(6) Uiso d 1 H
H4 0.2113(10) 0.244(3) 0.4009(15) 0.051(6) Uiso d 1 H
H9 0.0528(9) 0.622(2) 0.3545(14) 0.044(5) Uiso d 1 H
H1N2 0.0938(10) -0.064(3) 0.4724(16) 0.056(7) Uiso d 1 H
H2N3 -0.0283(10) 0.048(3) 0.2862(16) 0.053(6) Uiso d 1 H
H2N6 0.2651(11) 0.242(3) 0.7954(18) 0.061(7) Uiso d 1 H
H3 0.1884(10) 0.438(3) 0.2863(15) 0.055(6) Uiso d 1 H
H10 0.1083(10) 0.757(3) 0.3103(16) 0.057(6) Uiso d 1 H
H1N5 0.1125(9) 0.241(3) 0.6089(14) 0.046(6) Uiso d 1 H
H1 0.0393(10) 0.314(3) 0.2474(15) 0.053(6) Uiso d 1 H
H2 0.0832(10) 0.479(3) 0.1881(17) 0.059(7) Uiso d 1 H
H11 0.2146(10) 0.688(3) 0.4259(15) 0.055(6) Uiso d 1 H
H1N3 -0.0685(10) -0.031(3) 0.3020(15) 0.052(6) Uiso d 1 H
H15C 0.0476(12) 0.289(4) 0.4647(19) 0.081(9) Uiso d 1 H
H15B 0.0455(12) 0.434(3) 0.4998(19) 0.069(8) Uiso d 1 H
H7B 0.1721(14) -0.036(4) 0.487(2) 0.098(11) Uiso d 1 H
H1N6 0.2436(10) 0.343(3) 0.7228(16) 0.055(7) Uiso d 1 H
H15A 0.0335(13) 0.443(4) 0.414(2) 0.087(9) Uiso d 1 H
H1W1 0.1449(12) -0.119(4) 0.638(2) 0.077(9) Uiso d 1 H
H7A 0.2030(15) 0.095(4) 0.496(2) 0.105(11) Uiso d 1 H
H7C 0.1744(16) 0.087(4) 0.533(3) 0.118(13) Uiso d 1 H
H2W1 0.1079(16) -0.221(4) 0.577(2) 0.103(12) Uiso d 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Fe1 0.02975(10) 0.02907(11) 0.03392(11) -0.00654(8) 0.02005(9) -0.00174(8)
S1 0.0432(2) 0.0509(3) 0.0591(3) 0.00106(19) 0.0316(2) 0.0209(2)
S2 0.03445(19) 0.0438(2) 0.03548(19) 0.00544(16) 0.01979(16) 0.00768(17)
N1 0.0275(5) 0.0294(6) 0.0346(6) -0.0042(5) 0.0167(5) 0.0003(5)
N2 0.0279(6) 0.0337(7) 0.0373(7) -0.0001(5) 0.0162(5) 0.0076(5)
N3 0.0277(6) 0.0607(11) 0.0470(8) -0.0028(6) 0.0165(6) 0.0182(8)
N4 0.0370(7) 0.0398(8) 0.0373(7) -0.0035(6) 0.0230(6) 0.0022(6)
N5 0.0306(6) 0.0433(8) 0.0358(7) -0.0019(6) 0.0181(6) 0.0065(6)
N6 0.0324(7) 0.0674(12) 0.0461(9) -0.0065(7) 0.0166(7) 0.0101(9)
C1 0.0363(8) 0.0445(9) 0.0336(7) -0.0136(7) 0.0167(7) -0.0038(7)
C2 0.0619(12) 0.0541(12) 0.0376(9) -0.0180(10) 0.0301(9) -0.0043(8)
C3 0.0665(12) 0.0515(11) 0.0659(12) -0.0195(10) 0.0541(11) -0.0144(10)
C4 0.0384(8) 0.0381(9) 0.0612(11) -0.0090(7) 0.0352(9) -0.0122(8)
C5 0.0305(7) 0.0315(7) 0.0383(7) -0.0096(6) 0.0202(6) -0.0085(6)
C6 0.0271(6) 0.0269(7) 0.0358(7) -0.0049(5) 0.0167(6) -0.0071(6)
C7 0.0272(7) 0.0453(11) 0.0493(10) -0.0030(7) 0.0133(7) 0.0030(8)
C8 0.0303(7) 0.0308(7) 0.0381(7) -0.0011(5) 0.0206(6) 0.0015(6)
C9 0.0484(9) 0.0345(8) 0.0509(10) 0.0082(7) 0.0338(8) 0.0084(7)
C10 0.0688(13) 0.0278(8) 0.0587(11) 0.0017(8) 0.0442(11) 0.0081(8)
C11 0.0565(11) 0.0355(9) 0.0551(10) -0.0206(8) 0.0381(9) -0.0107(8)
C12 0.0401(8) 0.0367(9) 0.0398(8) -0.0139(7) 0.0236(7) -0.0081(7)
C13 0.0395(7) 0.0273(7) 0.0382(7) -0.0034(6) 0.0257(6) -0.0024(6)
C14 0.0362(7) 0.0308(7) 0.0369(7) -0.0007(6) 0.0247(6) -0.0006(6)
C15 0.0362(8) 0.0567(13) 0.0505(10) 0.0021(8) 0.0265(8) 0.0160(9)
C16 0.0313(7) 0.0392(8) 0.0320(7) 0.0021(6) 0.0190(6) -0.0015(6)
O1W 0.0539(9) 0.0672(11) 0.0427(8) 0.0005(8) 0.0177(7) -0.0026(8)
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'
S S 0.1246 0.1234 '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'
O O 0.0106 0.0060 '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_publ_flag
C1 Fe1 C10 124.55(9) ?
C1 Fe1 C9 107.06(8) ?
C10 Fe1 C9 40.76(7) ?
C1 Fe1 C2 40.84(7) ?
C10 Fe1 C2 104.39(9) ?
C9 Fe1 C2 116.98(9) ?
C1 Fe1 C11 161.41(8) ?
C10 Fe1 C11 40.47(9) ?
C9 Fe1 C11 68.50(8) ?
C2 Fe1 C11 123.67(8) ?
C1 Fe1 C4 68.60(8) ?
C10 Fe1 C4 151.49(8) ?
C9 Fe1 C4 167.41(7) ?
C2 Fe1 C4 68.06(9) ?
C11 Fe1 C4 119.44(8) ?
C1 Fe1 C3 68.34(8) ?
C10 Fe1 C3 116.26(8) ?
C9 Fe1 C3 150.52(9) ?
C2 Fe1 C3 40.31(9) ?
C11 Fe1 C3 106.14(8) ?
C4 Fe1 C3 40.28(9) ?
C1 Fe1 C12 156.42(7) ?
C10 Fe1 C12 68.30(8) ?
C9 Fe1 C12 68.71(8) ?
C2 Fe1 C12 162.32(7) ?
C11 Fe1 C12 40.57(7) ?
C4 Fe1 C12 110.22(8) ?
C3 Fe1 C12 127.01(8) ?
C1 Fe1 C13 120.65(7) ?
C10 Fe1 C13 68.55(7) ?
C9 Fe1 C13 40.85(7) ?
C2 Fe1 C13 153.16(8) ?
C11 Fe1 C13 68.60(7) ?
C4 Fe1 C13 130.22(8) ?
C3 Fe1 C13 166.30(8) ?
C12 Fe1 C13 40.98(7) ?
C1 Fe1 C5 40.96(7) ?
C10 Fe1 C5 163.93(8) ?
C9 Fe1 C5 128.17(7) ?
C2 Fe1 C5 68.68(8) ?
C11 Fe1 C5 155.37(8) ?
C4 Fe1 C5 40.98(6) ?
C3 Fe1 C5 68.47(7) ?
C12 Fe1 C5 122.43(7) ?
C13 Fe1 C5 110.70(6) ?
C6 N1 N2 117.34(13) ?
C8 N2 N1 119.97(13) ?
C14 N4 N5 117.76(13) ?
C16 N5 N4 118.15(14) ?
C2 C1 C5 108.4(2) ?
C2 C1 Fe1 70.00(10) ?
C5 C1 Fe1 70.53(9) ?
C3 C2 C1 108.0(2) ?
C3 C2 Fe1 70.00(10) ?
C1 C2 Fe1 69.10(10) ?
C2 C3 C4 108.6(2) ?
C2 C3 Fe1 69.70(10) ?
C4 C3 Fe1 69.86(10) ?
C3 C4 C5 108.4(2) ?
C3 C4 Fe1 69.86(11) ?
C5 C4 Fe1 69.92(10) ?
C1 C5 C4 106.5(2) ?
C1 C5 C6 127.11(14) ?
C4 C5 C6 126.35(16) ?
C1 C5 Fe1 68.51(10) ?
C4 C5 Fe1 69.10(9) ?
C6 C5 Fe1 127.12(11) ?
N1 C6 C5 116.20(10) y
N1 C6 C7 124.7(2) y
C5 C6 C7 119.10(10) ?
N3 C8 N2 117.6(2) y
N3 C8 S1 121.80(10) y
N2 C8 S1 120.60(10) y
C10 C9 C13 107.9(2) ?
C10 C9 Fe1 69.56(11) ?
C13 C9 Fe1 69.90(9) ?
C11 C10 C9 108.5(2) ?
C11 C10 Fe1 69.93(11) ?
C9 C10 Fe1 69.68(10) ?
C10 C11 C12 108.3(2) ?
C10 C11 Fe1 69.59(11) ?
C12 C11 Fe1 69.88(9) ?
C11 C12 C13 107.9(2) ?
C11 C12 Fe1 69.55(10) ?
C13 C12 Fe1 69.57(9) ?
C9 C13 C12 107.5(2) ?
C9 C13 C14 125.6(2) ?
C12 C13 C14 126.82(15) ?
C9 C13 Fe1 69.25(10) ?
C12 C13 Fe1 69.45(9) ?
C14 C13 Fe1 123.79(11) ?
N4 C14 C13 116.42(14) y
N4 C14 C15 125.36(15) y
C13 C14 C15 118.21(15) ?
N6 C16 N5 116.7(2) y
N6 C16 S2 122.70(10) y
N5 C16 S2 120.70(10) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Fe1 C1 2.037(2) ?
Fe1 C10 2.046(2) ?
Fe1 C9 2.047(2) ?
Fe1 C2 2.049(2) ?
Fe1 C11 2.050(2) ?
Fe1 C4 2.053(2) ?
Fe1 C3 2.053(2) ?
Fe1 C12 2.054(2) ?
Fe1 C13 2.056(2) ?
Fe1 C5 2.064(2) ?
S1 C8 1.687(2) y
S2 C16 1.699(2) y
N1 C6 1.292(2) y
N1 N2 1.382(2) y
N2 C8 1.354(2) y
N3 C8 1.318(2) y
N4 C14 1.286(2) y
N4 N5 1.388(2) y
N5 C16 1.348(2) y
N6 C16 1.330(2) y
C1 C2 1.425(3) ?
C1 C5 1.435(2) ?
C2 C3 1.413(3) ?
C3 C4 1.414(3) ?
C4 C5 1.441(2) ?
C5 C6 1.466(2) ?
C6 C7 1.501(2) ?
C9 C10 1.425(3) ?
C9 C13 1.432(2) ?
C10 C11 1.417(3) ?
C11 C12 1.423(3) ?
C12 C13 1.439(2) ?
C13 C14 1.467(2) ?
C14 C15 1.497(2) ?
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
O1W H1W1 S2 1_555 0.82(3) 2.50(3) 3.311(2) 169(4) yes
N2 H1N2 O1W 1_555 0.92(3) 2.15(2) 3.013(2) 157(3) yes
N6 H1N6 N4 1_555 0.81(3) 2.27(3) 2.604(3) 105(2) yes
O1W H2W1 S1 1_555 0.88(5) 2.53(4) 3.272(2) 143(3) yes
N3 H2N3 N1 1_555 0.88(3) 2.29(3) 2.656(3) 105(2) yes
N3 H1N3 S2 5_556 0.88(3) 2.64(3) 3.512(2) 175(2) yes
N5 H1N5 S1 5_556 0.82(3) 2.86(3) 3.656(2) 163(2) yes
N3 H3N3 N1 2_555 0.88(3) 2.43(2) 3.128(2) 137(2) yes
N6 H2N6 O1W 4_556 0.81(3) 2.35(3) 2.962(3) 133(3) yes