#------------------------------------------------------------------------------
#$Date: 2017-07-27 05:04:43 +0300 (Thu, 27 Jul 2017) $
#$Revision: 199356 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/87/7228766.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_7228766
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, C10 H4 I2'
_chemical_formula_sum            'C20 H14 Fe I2'
_chemical_formula_weight         563.96
_chemical_name_systematic        'ferrocene 1,4-bis(iodoethynyl)benzene'
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/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                 118.987(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.501(5)
_cell_length_b                   8.851(4)
_cell_length_c                   9.680(4)
_cell_measurement_reflns_used    1179
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      3
_cell_volume                     936.9(7)
_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      293(2)
_diffrn_measured_fraction_theta_full 1.000
_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  0.0210
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5206
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.997
_diffrn_reflns_theta_min         2.405
_exptl_absorpt_coefficient_mu    4.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_description       plate
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.639
_exptl_transmission_factor_min   0.480
_refine_diff_density_max         1.009
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.0072(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     51
_refine_ls_number_reflns         1331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0360
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0300P)²+4.2200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0931
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1066
_reflns_number_total             1331
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c7ce00857k2.cif
_cod_data_source_block           11_a
_cod_original_cell_volume        936.9(6)
_cod_database_code               7228766
_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   0.480
_shelx_estimated_absorpt_t_max   0.639
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 1.0000 0.5000 0.5000 0.0638(4) Uani 1 4 d S T P . .
C1 C 0.8445(5) 0.5571(7) 0.2943(6) 0.0684(12) Uani 0.5 1 d G . P A 1
H1A H 0.8412 0.5862 0.1968 0.082 Uiso 0.5 1 d R U P A 1
C2 C 0.8517(7) 0.6546(6) 0.4150(8) 0.0684(12) Uani 0.5 1 d G . P A 1
H2A H 0.8586 0.7626 0.4164 0.082 Uiso 0.5 1 d R U P A 1
C3 C 0.8564(5) 0.5635(8) 0.5386(6) 0.0684(12) Uani 0.5 1 d G . P A 1
H3A H 0.8647 0.5995 0.6369 0.082 Uiso 0.5 1 d R U P A 1
C4 C 0.8521(5) 0.4098(7) 0.4943(7) 0.0684(12) Uani 0.5 1 d G . P A 1
H4A H 0.8507 0.3238 0.5539 0.082 Uiso 0.5 1 d R U P A 1
C5 C 0.8447(6) 0.4058(7) 0.3433(7) 0.0684(12) Uani 0.5 1 d G . P A 1
H5A H 0.8360 0.3167 0.2821 0.082 Uiso 0.5 1 d R U P A 1
I1 I 0.54627(3) 0.5000 0.27839(6) 0.0768(3) Uani 1 2 d S T P . .
C1I C 0.3649(5) 0.5000 0.1829(7) 0.0559(13) Uani 1 2 d S T P . .
C2I C 0.2574(5) 0.5000 0.1301(7) 0.0526(13) Uani 1 2 d S T P . .
C3I C 0.1268(4) 0.5000 0.0635(6) 0.0470(11) Uani 1 2 d S T P . .
C4I C 0.0631(3) 0.3656(5) 0.0311(6) 0.0627(11) Uani 1 1 d . . . . .
H4IA H 0.1049 0.2744 0.0510 0.075 Uiso 1 1 calc 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
C5 Fe1 C5 130.1(6) 5_766 6_565
C5 Fe1 C5 49.9(10) 5_766 2_756
C5 Fe1 C5 180.0(6) 6_565 2_756
C5 Fe1 C5 180.0(7) 5_766 .
C5 Fe1 C5 49.9(3) 6_565 .
C5 Fe1 C5 130.1(5) 2_756 .
C5 Fe1 C4 138.1(4) 5_766 .
C5 Fe1 C4 66.1(2) 6_565 .
C5 Fe1 C4 113.9(4) 2_756 .
C5 Fe1 C4 41.94(12) . .
C5 Fe1 C4 41.94(12) 5_766 5_766
C5 Fe1 C4 113.9(6) 6_565 5_766
C5 Fe1 C4 66.1(7) 2_756 5_766
C5 Fe1 C4 138.1(4) . 5_766
C4 Fe1 C4 180.0(6) . 5_766
C5 Fe1 C4 113.9(6) 5_766 6_565
C5 Fe1 C4 41.94(11) 6_565 6_565
C5 Fe1 C4 138.1(4) 2_756 6_565
C5 Fe1 C4 66.1(3) . 6_565
C4 Fe1 C4 47.3(4) . 6_565
C4 Fe1 C4 132.7(6) 5_766 6_565
C5 Fe1 C4 66.1(7) 5_766 2_756
C5 Fe1 C4 138.1(4) 6_565 2_756
C5 Fe1 C4 41.9(3) 2_756 2_756
C5 Fe1 C4 113.9(4) . 2_756
C4 Fe1 C4 132.7(5) . 2_756
C4 Fe1 C4 47.3(10) 5_766 2_756
C4 Fe1 C4 180.0(6) 6_565 2_756
C5 Fe1 C1 138.9(5) 5_766 .
C5 Fe1 C1 16.2(2) 6_565 .
C5 Fe1 C1 163.8(5) 2_756 .
C5 Fe1 C1 41.10(9) . .
C4 Fe1 C1 69.07(10) . .
C4 Fe1 C1 110.9(5) 5_766 .
C4 Fe1 C1 56.38(11) 6_565 .
C4 Fe1 C1 123.6(4) 2_756 .
C5 Fe1 C1 16.2(5) 5_766 2_756
C5 Fe1 C1 138.90(12) 6_565 2_756
C5 Fe1 C1 41.1(5) 2_756 2_756
C5 Fe1 C1 163.8(3) . 2_756
C4 Fe1 C1 123.62(16) . 2_756
C4 Fe1 C1 56.4(4) 5_766 2_756
C4 Fe1 C1 110.92(17) 6_565 2_756
C4 Fe1 C1 69.1(4) 2_756 2_756
C1 Fe1 C1 151.6(4) . 2_756
C5 Fe1 C1 163.8(5) 5_766 6_565
C5 Fe1 C1 41.10(12) 6_565 6_565
C5 Fe1 C1 138.9(5) 2_756 6_565
C5 Fe1 C1 16.2(3) . 6_565
C4 Fe1 C1 56.38(16) . 6_565
C4 Fe1 C1 123.6(4) 5_766 6_565
C4 Fe1 C1 69.08(17) 6_565 6_565
C4 Fe1 C1 110.9(4) 2_756 6_565
C1 Fe1 C1 28.4(4) . 6_565
C1 Fe1 C1 180.0 2_756 6_565
C5 Fe1 C1 41.1(5) 5_766 5_766
C5 Fe1 C1 163.8(2) 6_565 5_766
C5 Fe1 C1 16.2(5) 2_756 5_766
C5 Fe1 C1 138.90(9) . 5_766
C4 Fe1 C1 110.92(10) . 5_766
C4 Fe1 C1 69.1(5) 5_766 5_766
C4 Fe1 C1 123.62(11) 6_565 5_766
C4 Fe1 C1 56.4(4) 2_756 5_766
C1 Fe1 C1 180.0(3) . 5_766
C1 Fe1 C1 28.4(4) 2_756 5_766
C1 Fe1 C1 151.6(4) 6_565 5_766
C5 C1 C1 124.8(10) 6_565 6_565
C5 C1 C5 105.4(10) 6_565 .
C1 C1 C5 19.46(19) 6_565 .
C5 C1 C2 4.0(7) 6_565 .
C1 C1 C2 127.42(19) 6_565 .
C5 C1 C2 108.0 . .
C5 C1 C4 26.1(7) 6_565 6_565
C1 C1 C4 98.8(3) 6_565 6_565
C5 C1 C4 79.4(4) . 6_565
C2 C1 C4 28.6(4) . 6_565
C5 C1 Fe1 73.6(5) 6_565 .
C1 C1 Fe1 75.82(18) 6_565 .
C5 C1 Fe1 66.3(3) . .
C2 C1 Fe1 72.5(2) . .
C4 C1 Fe1 59.9(2) 6_565 .
C5 C1 H1A 129.6 6_565 .
C1 C1 H1A 105.6 6_565 .
C5 C1 H1A 125.0 . .
C2 C1 H1A 127.0 . .
C4 C1 H1A 155.6 6_565 .
Fe1 C1 H1A 125.9 . .
C5 C2 C4 104.0(12) 6_565 6_565
C5 C2 C3 106.2(6) 6_565 .
C4 C2 C3 2.8(5) 6_565 .
C5 C2 C1 2.7(4) 6_565 .
C4 C2 C1 105.8(6) 6_565 .
C3 C2 C1 108.0 . .
C5 C2 Fe1 68.6(5) 6_565 .
C4 C2 Fe1 68.9(5) 6_565 .
C3 C2 Fe1 68.7(2) . .
C1 C2 Fe1 67.8(2) . .
C5 C2 H2A 127.8 6_565 .
C4 C2 H2A 128.2 6_565 .
C3 C2 H2A 125.9 . .
C1 C2 H2A 125.9 . .
Fe1 C2 H2A 125.5 . .
C4 C3 C3 120.2(14) 6_565 6_565
C4 C3 C4 103.6(14) 6_565 .
C3 C3 C4 16.6 6_565 .
C4 C3 C2 5.6(11) 6_565 .
C3 C3 C2 124.6 6_565 .
C4 C3 C2 108.0 . .
C4 C3 C5 21.9(11) 6_565 6_565
C3 C3 C5 98.5(4) 6_565 6_565
C4 C3 C5 81.9(4) . 6_565
C2 C3 C5 26.1(4) . 6_565
C4 C3 Fe1 72.5(7) 6_565 .
C3 C3 Fe1 74.3(3) 6_565 .
C4 C3 Fe1 66.2(3) . .
C2 C3 Fe1 71.9(2) . .
C5 C3 Fe1 60.2(2) 6_565 .
C4 C3 H3A 130.4 6_565 .
C3 C3 H3A 109.4 6_565 .
C4 C3 H3A 126.0 . .
C2 C3 H3A 126.0 . .
C5 C3 H3A 152.1 6_565 .
Fe1 C3 H3A 125.4 . .
C3 C4 C2 171.6(16) 6_565 6_565
C3 C4 C3 43.2(15) 6_565 .
C2 C4 C3 143.1(6) 6_565 .
C3 C4 C5 151.0(15) 6_565 .
C2 C4 C5 35.3(6) 6_565 .
C3 C4 C5 108.0 . .
C3 C4 C4 59.8(15) 6_565 6_565
C2 C4 C4 126.7(6) 6_565 6_565
C3 C4 C4 16.6 . 6_565
C5 C4 C4 91.4 . 6_565
C3 C4 C1 140.8(17) 6_565 6_565
C2 C4 C1 45.5(3) 6_565 6_565
C3 C4 C1 97.7(4) . 6_565
C5 C4 C1 10.3(4) . 6_565
C4 C4 C1 81.2(4) 6_565 6_565
C3 C4 Fe1 94.5(9) 6_565 .
C2 C4 Fe1 84.5(3) 6_565 .
C3 C4 Fe1 73.0(3) . .
C5 C4 Fe1 68.6(2) . .
C4 C4 Fe1 66.3(3) 6_565 .
C1 C4 Fe1 63.7(3) 6_565 .
C3 C4 H4A 83.0 6_565 .
C2 C4 H4A 90.9 6_565 .
C3 C4 H4A 126.0 . .
C5 C4 H4A 126.0 . .
C4 C4 H4A 142.4 6_565 .
C1 C4 H4A 136.2 6_565 .
Fe1 C4 H4A 126.0 . .
C1 C5 C2 173.3(11) 6_565 6_565
C1 C5 C1 35.7(10) 6_565 .
C2 C5 C1 148.4(6) 6_565 .
C1 C5 C4 143.7(10) 6_565 .
C2 C5 C4 40.7(6) 6_565 .
C1 C5 C4 108.0 . .
C1 C5 C5 55.2(10) 6_565 6_565
C2 C5 C5 129.1(6) 6_565 6_565
C1 C5 C5 19.5 . 6_565
C4 C5 C5 88.6 . 6_565
C1 C5 C3 136.6(13) 6_565 6_565
C2 C5 C3 47.7(3) 6_565 6_565
C1 C5 C3 101.0(4) . 6_565
C4 C5 C3 7.1(4) . 6_565
C5 C5 C3 81.5(4) 6_565 6_565
C1 C5 Fe1 90.1(9) 6_565 .
C2 C5 Fe1 87.9(3) 6_565 .
C1 C5 Fe1 72.6(3) . .
C4 C5 Fe1 69.5(2) . .
C5 C5 Fe1 65.1(3) 6_565 .
C3 C5 Fe1 65.8(3) 6_565 .
C1 C5 H5A 90.4 6_565 .
C2 C5 H5A 85.6 6_565 .
C1 C5 H5A 125.9 . .
C4 C5 H5A 125.9 . .
C5 C5 H5A 145.2 6_565 .
C3 C5 H5A 133.0 6_565 .
Fe1 C5 H5A 126.5 . .
C2I C1I I1 178.2(6) . .
C1I C2I C3I 179.1(6) . .
C4I C3I C4I 119.0(5) . 6_565
C4I C3I C2I 120.5(2) . .
C4I C3I C2I 120.5(2) 6_565 .
C3I C4I C4I 120.5(2) . 2
C3I C4I H4IA 119.8 . .
C4I C4I H4IA 119.8 2 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Fe1 C5 1.978(6) 5_766
Fe1 C5 1.978(5) 6_565
Fe1 C5 1.978(12) 2_756
Fe1 C5 1.978(6) .
Fe1 C4 1.990(6) .
Fe1 C4 1.990(6) 5_766
Fe1 C4 1.990(6) 6_565
Fe1 C4 1.990(12) 2_756
Fe1 C1 2.061(5) .
Fe1 C1 2.061(5) 2_756
Fe1 C1 2.061(5) 6_565
Fe1 C1 2.061(5) 5_766
C1 C5 0.576(7) 6_565
C1 C1 1.010(13) 6_565
C1 C5 1.4200 .
C1 C2 1.4200 .
C1 C4 1.915(2) 6_565
C1 H1A 0.9600 .
C2 C5 0.846(7) 6_565
C2 C4 0.954(8) 6_565
C2 C3 1.4200 .
C2 H2A 0.9600 .
C3 C4 0.469(7) 6_565
C3 C3 1.125(15) 6_565
C3 C4 1.4200 .
C3 C5 1.8448(19) 6_565
C3 H3A 0.9600 .
C4 C3 0.469(7) 6_565
C4 C2 0.954(7) 6_565
C4 C5 1.4200 .
C4 C4 1.597(13) 6_565
C4 C1 1.915(5) 6_565
C4 H4A 0.9600 .
C5 C1 0.576(9) 6_565
C5 C2 0.846(7) 6_565
C5 C5 1.668(12) 6_565
C5 C3 1.845(2) 6_565
C5 H5A 0.9600 .
I1 C1I 1.991(6) .
C1I C2I 1.184(8) .
C2I C3I 1.436(7) .
C3I C4I 1.380(5) .
C3I C4I 1.380(5) 6_565
C4I C4I 1.389(8) 2
C4I H4IA 0.9300 .
