#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:30:50 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179249 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/69/4316938.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_4316938
loop_
_publ_author_name
'Yuji Miura'
'Fumiko Shimizu'
'Tomoyuki Mochida'
_publ_section_title
;
 Preparation, Properties, and Crystal Structures of Organometallic Ionic
 Liquids Comprising 1-Ferrocenyl-3-alkylimidazolium-Based Salts of
 Bis(trifluoromethanesulfonyl)amide and Hexafluorophosphate
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10032
_journal_page_last               10040
_journal_paper_doi               10.1021/ic1013363
_journal_volume                  49
_journal_year                    2010
_chemical_formula_moiety         'C13 H14 Fe N3, I'
_chemical_formula_sum            'C13 H14 Fe I N3'
_chemical_formula_weight         395.02
_chemical_name_systematic
;
 Ferrocenylmethyltriazole iodide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 98.553(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.163(4)
_cell_length_b                   13.981(5)
_cell_length_c                   9.696(3)
_cell_measurement_reflns_used    2485
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      2.50
_cell_volume                     1362.4(8)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            15227
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    3.358
_exptl_absorpt_correction_T_max  0.8239
_exptl_absorpt_correction_T_min  0.1887
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.926
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.257
_refine_diff_density_min         -1.121
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         5587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0424
_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/[σ²(Fo²)+(0.0643P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1127
_reflns_number_gt                4674
_reflns_number_total             5587
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic1013363_si_002_2.cif
_cod_data_source_block           9-I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4316938
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
I1 I 0.86575(2) 0.400102(16) 0.22993(3) 0.01660(10) Uani 1 1 d . . .
Fe2 Fe 0.39847(5) 0.56394(4) 0.23871(5) 0.01264(13) Uani 1 1 d . . .
C10 C 0.3860(4) 0.4447(2) 0.3588(4) 0.0168(8) Uani 1 1 d . . .
H10A H 0.4607 0.4164 0.4249 0.020 Uiso 1 1 calc R . .
C7 C 0.2095(3) 0.5362(2) 0.2675(4) 0.0143(7) Uani 1 1 d . . .
C9 C 0.3532(3) 0.4213(3) 0.2146(4) 0.0154(8) Uani 1 1 d . . .
H9A H 0.4007 0.3738 0.1627 0.019 Uiso 1 1 calc R . .
C12 C 0.0299(4) 0.6394(2) 0.1425(4) 0.0157(8) Uani 1 1 d . . .
H12A H 0.0509 0.6351 0.0504 0.019 Uiso 1 1 calc R . .
C8 C 0.2427(3) 0.4787(2) 0.1565(4) 0.0145(7) Uani 1 1 d . . .
H8A H 0.1970 0.4781 0.0577 0.017 Uiso 1 1 calc R . .
C4 C 0.5913(4) 0.6122(3) 0.2752(4) 0.0176(8) Uani 1 1 d . . .
H4A H 0.6655 0.5833 0.3413 0.021 Uiso 1 1 calc R . .
C3 C 0.5554(4) 0.5876(3) 0.1327(4) 0.0178(8) Uani 1 1 d . . .
H3A H 0.6000 0.5383 0.0808 0.021 Uiso 1 1 calc R . .
C6 C 0.2962(3) 0.5162(2) 0.3925(4) 0.0162(8) Uani 1 1 d . . .
H6A H 0.2946 0.5463 0.4858 0.019 Uiso 1 1 calc R . .
C1 C 0.4117(4) 0.7049(3) 0.1857(4) 0.0206(9) Uani 1 1 d . . .
H1A H 0.3377 0.7526 0.1776 0.025 Uiso 1 1 calc R . .
C2 C 0.4437(4) 0.6447(3) 0.0763(4) 0.0181(8) Uani 1 1 d . . .
H2A H 0.3967 0.6431 -0.0220 0.022 Uiso 1 1 calc R . .
C11 C 0.0322(4) 0.6245(3) 0.3656(4) 0.0167(8) Uani 1 1 d . . .
H11A H 0.0586 0.6056 0.4598 0.020 Uiso 1 1 calc R . .
C13 C -0.1729(4) 0.7439(3) 0.0989(4) 0.0186(8) Uani 1 1 d . . .
H13A H -0.1594 0.7422 0.0010 0.028 Uiso 1 1 calc R . .
H13B H -0.1652 0.8100 0.1329 0.028 Uiso 1 1 calc R . .
H13C H -0.2617 0.7192 0.1072 0.028 Uiso 1 1 calc R . .
C5 C 0.5024(4) 0.6846(3) 0.3083(4) 0.0208(8) Uani 1 1 d . . .
H5A H 0.5034 0.7155 0.4015 0.025 Uiso 1 1 calc R . .
N1 N 0.0982(3) 0.6003(2) 0.2575(3) 0.0143(6) Uani 1 1 d . . .
N2 N -0.0719(3) 0.6770(2) 0.3221(3) 0.0173(7) Uani 1 1 d . . .
N3 N -0.0725(3) 0.6850(2) 0.1819(3) 0.0145(6) Uani 1 1 d . . .
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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
C7 Fe2 C2 122.66(15) . . ?
C7 Fe2 C1 108.60(15) . . ?
C2 Fe2 C1 40.91(15) . . ?
C7 Fe2 C8 41.01(14) . . ?
C2 Fe2 C8 105.70(15) . . ?
C1 Fe2 C8 122.62(15) . . ?
C7 Fe2 C10 67.96(14) . . ?
C2 Fe2 C10 158.00(15) . . ?
C1 Fe2 C10 159.83(16) . . ?
C8 Fe2 C10 68.77(14) . . ?
C7 Fe2 C3 158.09(15) . . ?
C2 Fe2 C3 40.84(15) . . ?
C1 Fe2 C3 68.50(15) . . ?
C8 Fe2 C3 120.87(15) . . ?
C10 Fe2 C3 122.36(15) . . ?
C7 Fe2 C5 124.49(15) . . ?
C2 Fe2 C5 68.64(15) . . ?
C1 Fe2 C5 40.57(15) . . ?
C8 Fe2 C5 159.74(15) . . ?
C10 Fe2 C5 123.70(16) . . ?
C3 Fe2 C5 68.37(15) . . ?
C7 Fe2 C6 40.71(14) . . ?
C2 Fe2 C6 159.29(15) . . ?
C1 Fe2 C6 123.70(15) . . ?
C8 Fe2 C6 69.37(14) . . ?
C10 Fe2 C6 40.67(14) . . ?
C3 Fe2 C6 158.99(15) . . ?
C5 Fe2 C6 108.66(15) . . ?
C7 Fe2 C9 68.13(14) . . ?
C2 Fe2 C9 121.39(15) . . ?
C1 Fe2 C9 158.34(16) . . ?
C8 Fe2 C9 40.73(13) . . ?
C10 Fe2 C9 40.71(15) . . ?
C3 Fe2 C9 106.13(14) . . ?
C5 Fe2 C9 158.88(16) . . ?
C6 Fe2 C9 68.75(14) . . ?
C7 Fe2 C4 160.48(16) . . ?
C2 Fe2 C4 68.47(15) . . ?
C1 Fe2 C4 68.27(15) . . ?
C8 Fe2 C4 157.22(15) . . ?
C10 Fe2 C4 107.94(15) . . ?
C3 Fe2 C4 40.46(15) . . ?
C5 Fe2 C4 40.63(15) . . ?
C6 Fe2 C4 123.75(15) . . ?
C9 Fe2 C4 122.11(15) . . ?
C6 C10 C9 108.8(3) . . ?
C6 C10 Fe2 69.8(2) . . ?
C9 C10 Fe2 69.8(2) . . ?
C6 C10 H10A 125.6 . . ?
C9 C10 H10A 125.6 . . ?
Fe2 C10 H10A 125.6 . . ?
C6 C7 C8 110.4(3) . . ?
C6 C7 N1 124.4(3) . . ?
C8 C7 N1 125.1(3) . . ?
C6 C7 Fe2 70.9(2) . . ?
C8 C7 Fe2 70.5(2) . . ?
N1 C7 Fe2 128.9(2) . . ?
C10 C9 C8 108.3(3) . . ?
C10 C9 Fe2 69.5(2) . . ?
C8 C9 Fe2 69.4(2) . . ?
C10 C9 H9A 125.8 . . ?
C8 C9 H9A 125.8 . . ?
Fe2 C9 H9A 125.8 . . ?
N3 C12 N1 106.7(3) . . ?
N3 C12 H12A 126.6 . . ?
N1 C12 H12A 126.6 . . ?
C7 C8 C9 106.3(3) . . ?
C7 C8 Fe2 68.5(2) . . ?
C9 C8 Fe2 69.9(2) . . ?
C7 C8 H8A 126.9 . . ?
C9 C8 H8A 126.9 . . ?
Fe2 C8 H8A 126.9 . . ?
C3 C4 C5 108.2(3) . . ?
C3 C4 Fe2 69.6(2) . . ?
C5 C4 Fe2 69.6(2) . . ?
C3 C4 H4A 125.9 . . ?
C5 C4 H4A 125.9 . . ?
Fe2 C4 H4A 125.9 . . ?
C4 C3 C2 108.2(3) . . ?
C4 C3 Fe2 70.0(2) . . ?
C2 C3 Fe2 69.4(2) . . ?
C4 C3 H3A 125.9 . . ?
C2 C3 H3A 125.9 . . ?
Fe2 C3 H3A 125.9 . . ?
C7 C6 C10 106.3(3) . . ?
C7 C6 Fe2 68.4(2) . . ?
C10 C6 Fe2 69.5(2) . . ?
C7 C6 H6A 126.9 . . ?
C10 C6 H6A 126.9 . . ?
Fe2 C6 H6A 126.9 . . ?
C5 C1 C2 108.2(3) . . ?
C5 C1 Fe2 69.9(2) . . ?
C2 C1 Fe2 69.5(2) . . ?
C5 C1 H1A 125.9 . . ?
C2 C1 H1A 125.9 . . ?
Fe2 C1 H1A 125.9 . . ?
C3 C2 C1 107.5(3) . . ?
C3 C2 Fe2 69.7(2) . . ?
C1 C2 Fe2 69.6(2) . . ?
C3 C2 H2A 126.3 . . ?
C1 C2 H2A 126.3 . . ?
Fe2 C2 H2A 126.3 . . ?
N2 C11 N1 110.9(3) . . ?
N2 C11 H11A 124.5 . . ?
N1 C11 H11A 124.5 . . ?
N3 C13 H13A 109.5 . . ?
N3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C5 C4 107.9(3) . . ?
C1 C5 Fe2 69.5(2) . . ?
C4 C5 Fe2 69.8(2) . . ?
C1 C5 H5A 126.0 . . ?
C4 C5 H5A 126.0 . . ?
Fe2 C5 H5A 126.0 . . ?
C12 N1 C11 106.6(3) . . ?
C12 N1 C7 128.0(3) . . ?
C11 N1 C7 125.0(3) . . ?
C11 N2 N3 104.6(3) . . ?
C12 N3 N2 111.2(3) . . ?
C12 N3 C13 129.0(3) . . ?
N2 N3 C13 119.7(3) . . ?
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
Fe2 C7 2.019(3) . ?
Fe2 C2 2.045(4) . ?
Fe2 C1 2.046(4) . ?
Fe2 C8 2.046(3) . ?
Fe2 C10 2.047(4) . ?
Fe2 C3 2.049(4) . ?
Fe2 C5 2.050(4) . ?
Fe2 C6 2.052(4) . ?
Fe2 C9 2.052(4) . ?
Fe2 C4 2.053(4) . ?
C10 C6 1.424(5) . ?
C10 C9 1.426(5) . ?
C10 H10A 1.0000 . ?
C7 C6 1.416(5) . ?
C7 C8 1.424(5) . ?
C7 N1 1.435(4) . ?
C9 C8 1.426(5) . ?
C9 H9A 1.0000 . ?
C12 N3 1.325(5) . ?
C12 N1 1.339(5) . ?
C12 H12A 0.9500 . ?
C8 H8A 1.0000 . ?
C4 C3 1.418(5) . ?
C4 C5 1.425(5) . ?
C4 H4A 1.0000 . ?
C3 C2 1.428(5) . ?
C3 H3A 1.0000 . ?
C6 H6A 1.0000 . ?
C1 C5 1.420(5) . ?
C1 C2 1.430(5) . ?
C1 H1A 1.0000 . ?
C2 H2A 1.0000 . ?
C11 N2 1.306(5) . ?
C11 N1 1.368(5) . ?
C11 H11A 0.9500 . ?
C13 N3 1.457(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C5 H5A 1.0000 . ?
N2 N3 1.363(4) . ?
