#------------------------------------------------------------------------------
#$Date: 2017-07-27 05:04:43 +0300 (Thu, 27 Jul 2017) $
#$Revision: 199356 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/87/7228767.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_7228767
loop_
_publ_author_name
'Torubaev, Yury'
'Lyssenko, Konstantin A.'
'Barzilovich, Petro Yu.'
'Mobin, Shaikh M.'
'Singh, Ajeet'
'Saratov, George A.'
'Mathur, Pradeep'
_publ_section_title
;
 Self-assembly of conducting cocrystals via iodine----π(Cp) interactions
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE00857K
_journal_year                    2017
_chemical_formula_moiety         'C10 H10 Fe, C8 H5 I'
_chemical_formula_sum            'C18 H15 Fe I'
_chemical_formula_weight         414.05
_chemical_name_systematic        'ferrocene iodophenylacetylene'
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2017-06-26 deposited with the CCDC.
2017-07-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.63(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5077(19)
_cell_length_b                   8.6571(17)
_cell_length_c                   10.041(2)
_cell_measurement_reflns_used    1224
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     768.3(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0095
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            39983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.982
_diffrn_reflns_theta_min         2.182
_exptl_absorpt_coefficient_mu    2.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.210
_exptl_transmission_factor_max   0.574
_exptl_transmission_factor_min   0.449
_refine_diff_density_max         1.545
_refine_diff_density_min         -1.194
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         2372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0177
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0291P)²+0.5267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0501
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2303
_reflns_number_total             2372
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c7ce00857k2.cif
_cod_data_source_block           a
_cod_database_code               7228767
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.449
_shelx_estimated_absorpt_t_max   0.574
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Fe1 Fe 0.65154(3) 0.2500 0.91871(3) 0.01118(6) Uani 1 2 d S T P
I1 I 0.79308(2) 0.7500 0.79760(2) 0.01999(5) Uani 1 2 d S T P
C1I C 0.5722(2) 0.7500 0.6766(2) 0.0183(3) Uani 1 2 d S T P
C2I C 0.4397(2) 0.7500 0.6038(2) 0.0170(3) Uani 1 2 d S T P
C3I C 0.2814(2) 0.7500 0.51477(19) 0.0166(3) Uani 1 2 d S T P
C4I C 0.20423(17) 0.89037(19) 0.47094(15) 0.0221(3) Uani 1 1 d . . .
H4I H 0.2564 0.9855 0.4998 0.027 Uiso 1 1 calc R U .
C5I C 0.05066(18) 0.8899(2) 0.38482(16) 0.0281(3) Uani 1 1 d . . .
H5I H -0.0016 0.9848 0.3549 0.034 Uiso 1 1 calc R U .
C6I C -0.0263(3) 0.7500 0.3426(2) 0.0294(5) Uani 1 2 d S T P
H6I H -0.1311 0.7500 0.2851 0.035 Uiso 1 2 calc R U P
C1 C 0.86366(14) 0.16725(16) 0.95058(14) 0.0161(2) Uani 1 1 d . . .
H1A H 0.8935 0.0941 0.8779 0.019 Uiso 1 1 d R U .
C2 C 0.81539(15) 0.38396(17) 1.06265(14) 0.0183(2) Uani 1 1 d . . .
H2A H 0.8032 0.5027 1.0895 0.022 Uiso 1 1 d R U .
C3 C 0.7861(2) 0.2500 1.1320(2) 0.0195(4) Uani 1 2 d S T P
H7A H 0.7475 0.2500 1.2206 0.023 Uiso 1 2 d R U P
C5 C 0.46076(15) 0.38412(17) 0.83428(14) 0.0176(2) Uani 1 1 d . . .
H5A H 0.4492 0.5027 0.8619 0.021 Uiso 1 1 d R U .
C6 C 0.4307(2) 0.2500 0.9036(2) 0.0179(3) Uani 1 2 d S T P
H10A H 0.3920 0.2500 0.9921 0.022 Uiso 1 2 d R U P
C7 C 0.51009(15) 0.16729(16) 0.72323(13) 0.0160(2) Uani 1 1 d . . .
H8A H 0.5423 0.0939 0.6522 0.019 Uiso 1 1 d R U .
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'
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
C6 Fe1 C2 122.97(6) . .
C6 Fe1 C2 122.97(6) . 4_565
C2 Fe1 C2 68.92(9) . 4_565
C6 Fe1 C3 107.78(8) . .
C2 Fe1 C3 40.89(5) . .
C2 Fe1 C3 40.89(5) 4_565 .
C6 Fe1 C1 158.99(4) . .
C2 Fe1 C1 68.87(6) . .
C2 Fe1 C1 40.91(5) 4_565 .
C3 Fe1 C1 68.78(7) . .
C6 Fe1 C1 158.99(4) . 4_565
C2 Fe1 C1 40.92(5) . 4_565
C2 Fe1 C1 68.87(6) 4_565 4_565
C3 Fe1 C1 68.78(7) . 4_565
C1 Fe1 C1 40.88(8) . 4_565
C6 Fe1 C5 40.95(5) . 4_565
C2 Fe1 C5 159.46(6) . 4_565
C2 Fe1 C5 107.28(6) 4_565 4_565
C3 Fe1 C5 123.15(6) . 4_565
C1 Fe1 C5 122.32(6) . 4_565
C1 Fe1 C5 158.32(6) 4_565 4_565
C6 Fe1 C5 40.95(5) . .
C2 Fe1 C5 107.28(6) . .
C2 Fe1 C5 159.46(6) 4_565 .
C3 Fe1 C5 123.15(6) . .
C1 Fe1 C5 158.32(6) . .
C1 Fe1 C5 122.32(6) 4_565 .
C5 Fe1 C5 68.80(8) 4_565 .
C6 Fe1 C7 68.73(7) . .
C2 Fe1 C7 158.41(6) . .
C2 Fe1 C7 122.40(6) 4_565 .
C3 Fe1 C7 159.04(4) . .
C1 Fe1 C7 106.67(6) . .
C1 Fe1 C7 122.01(6) 4_565 .
C5 Fe1 C7 40.73(5) 4_565 .
C5 Fe1 C7 68.63(6) . .
C6 Fe1 C7 68.73(7) . 4_565
C2 Fe1 C7 122.40(6) . 4_565
C2 Fe1 C7 158.41(6) 4_565 4_565
C3 Fe1 C7 159.04(4) . 4_565
C1 Fe1 C7 122.01(6) . 4_565
C1 Fe1 C7 106.67(6) 4_565 4_565
C5 Fe1 C7 68.63(6) 4_565 4_565
C5 Fe1 C7 40.73(5) . 4_565
C7 Fe1 C7 40.76(8) . 4_565
C2I C1I I1 179.90(18) . .
C1I C2I C3I 179.2(2) . .
C4I C3I C4I 119.89(19) 4_575 .
C4I C3I C2I 120.06(9) 4_575 .
C4I C3I C2I 120.06(9) . .
C5I C4I C3I 119.87(16) . .
C5I C4I H4I 120.1 . .
C3I C4I H4I 120.1 . .
C4I C5I C6I 120.13(17) . .
C4I C5I H5I 119.9 . .
C6I C5I H5I 119.9 . .
C5I C6I C5I 120.1(2) 4_575 .
C5I C6I H6I 120.0 4_575 .
C5I C6I H6I 120.0 . .
C1 C1 C2 108.02(8) 4_565 4_565
C1 C1 Fe1 69.56(4) 4_565 .
C2 C1 Fe1 69.49(8) 4_565 .
C1 C1 H1A 125.9 4_565 .
C2 C1 H1A 126.1 4_565 .
Fe1 C1 H1A 126.0 . .
C3 C2 C1 107.90(13) . 4_565
C3 C2 Fe1 69.58(9) . .
C1 C2 Fe1 69.60(8) 4_565 .
C3 C2 H2A 126.3 . .
C1 C2 H2A 125.8 4_565 .
Fe1 C2 H2A 126.3 . .
C2 C3 C2 108.17(17) . 4_565
C2 C3 Fe1 69.53(9) . .
C2 C3 Fe1 69.54(9) 4_565 .
C2 C3 H7A 125.9 . .
C2 C3 H7A 125.9 4_565 .
Fe1 C3 H7A 126.2 . .
C7 C5 C6 107.89(13) 4_565 .
C7 C5 Fe1 69.68(8) 4_565 .
C6 C5 Fe1 69.29(9) . .
C7 C5 H5A 126.2 4_565 .
C6 C5 H5A 125.9 . .
Fe1 C5 H5A 126.1 . .
C5 C6 C5 107.97(16) 4_565 .
C5 C6 Fe1 69.77(9) 4_565 .
C5 C6 Fe1 69.77(9) . .
C5 C6 H10A 126.0 4_565 .
C5 C6 H10A 126.0 . .
Fe1 C6 H10A 126.1 . .
C5 C7 C7 108.12(8) 4_565 4_565
C5 C7 Fe1 69.59(7) 4_565 .
C7 C7 Fe1 69.62(4) 4_565 .
C5 C7 H8A 125.8 4_565 .
C7 C7 H8A 126.0 4_565 .
Fe1 C7 H8A 126.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 C6 2.0487(19) .
Fe1 C2 2.0496(15) .
Fe1 C2 2.0496(15) 4_565
Fe1 C3 2.050(2) .
Fe1 C1 2.0511(13) .
Fe1 C1 2.0512(13) 4_565
Fe1 C5 2.0551(14) 4_565
Fe1 C5 2.0551(14) .
Fe1 C7 2.0562(14) .
Fe1 C7 2.0562(14) 4_565
I1 C1I 2.001(2) .
C1I C2I 1.201(3) .
C2I C3I 1.439(3) .
C3I C4I 1.4040(18) 4_575
C3I C4I 1.4040(18) .
C4I C5I 1.396(2) .
C4I H4I 0.9500 .
C5I C6I 1.397(2) .
C5I H5I 0.9500 .
C6I C5I 1.397(2) 4_575
C6I H6I 0.9500 .
C1 C1 1.433(3) 4_565
C1 C2 1.4333(19) 4_565
C1 H1A 1.0801 .
C2 C3 1.4320(19) .
C2 C1 1.4333(18) 4_565
C2 H2A 1.0800 .
C3 C2 1.4320(19) 4_565
C3 H7A 1.0800 .
C5 C7 1.4307(18) 4_565
C5 C6 1.4355(18) .
C5 H5A 1.0800 .
C6 C5 1.4354(18) 4_565
C6 H10A 1.0800 .
C7 C5 1.4307(18) 4_565
C7 C7 1.432(3) 4_565
C7 H8A 1.0799 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C4I C3I C4I C5I 0.5(3) 4_575 .
C2I C3I C4I C5I -179.87(15) . .
C3I C4I C5I C6I 0.2(2) . .
C4I C5I C6I C5I -0.9(3) . 4_575
C1 C2 C3 C2 -0.3(2) 4_565 4_565
Fe1 C2 C3 C2 58.99(13) . 4_565
C1 C2 C3 Fe1 -59.27(10) 4_565 .
C7 C5 C6 C5 -0.3(2) 4_565 4_565
Fe1 C5 C6 C5 -59.53(13) . 4_565
C7 C5 C6 Fe1 59.18(10) 4_565 .
