#------------------------------------------------------------------------------
#$Date: 2020-12-10 05:27:11 +0200 (Thu, 10 Dec 2020) $
#$Revision: 259727 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/17/7241707.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_7241707
loop_
_publ_author_name
'Jakupec, Nikola'
'Fotović, Luka'
'Stilinović, Vladimir'
_publ_section_title
;
 The effect of halogen bonding on protonated hexacyanoferrate networks in
 hexacyanoferrates of halogenopyridines
;
_journal_issue                   46
_journal_name_full               CrystEngComm
_journal_page_first              8142
_journal_page_last               8150
_journal_paper_doi               10.1039/D0CE01359E
_journal_volume                  22
_journal_year                    2020
_chemical_formula_sum            'C18 H20 Fe I2 N8 O2'
_chemical_formula_weight         690.07
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-09-14 deposited with the CCDC.	2020-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.027(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8231(4)
_cell_length_b                   11.0729(3)
_cell_length_c                   13.2703(7)
_cell_measurement_reflns_used    3835
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.4017
_cell_measurement_theta_min      4.0015
_cell_volume                     1246.08(10)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7757
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_min         4.012
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58060
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.752
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.872
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2680
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      0.872
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0301
_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)+(0.0365P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0661
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1932
_reflns_number_total             2680
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01359e2.cif
_cod_data_source_block           HCF_4IPy
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7241707
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_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_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
I1 I 0.33870(3) 0.89672(2) 0.06256(2) 0.05686(11) Uani 1 1 d . . . . .
Fe1 Fe 0.500000 0.500000 0.000000 0.01993(13) Uani 1 2 d S . P . .
N4 N 0.0639(3) 1.2730(3) 0.0237(3) 0.0470(7) Uani 1 1 d D U . . .
C3 C 0.5252(3) 0.6163(3) -0.0970(2) 0.0266(6) Uani 1 1 d . . . . .
C4 C 0.1348(4) 1.2422(4) -0.0485(3) 0.0497(6) Uani 1 1 d . U . . .
H4 H 0.131497 1.293824 -0.104380 0.060 Uiso 1 1 calc R U . . .
N2 N 0.5666(3) 0.6851(2) 0.1784(2) 0.0408(7) Uani 1 1 d . . . . .
C1 C 0.2787(3) 0.5352(2) -0.0341(2) 0.0271(6) Uani 1 1 d . . . . .
C2 C 0.5416(3) 0.6169(2) 0.1106(2) 0.0264(6) Uani 1 1 d . . . . .
C8 C 0.0660(4) 1.2026(3) 0.1051(3) 0.0497(6) Uani 1 1 d . . . . .
H8 H 0.013617 1.226724 0.153646 0.060 Uiso 1 1 calc R U . . .
C5 C 0.2124(4) 1.1350(3) -0.0408(3) 0.0462(6) Uani 1 1 d . . . . .
H5 H 0.261876 1.112632 -0.091392 0.055 Uiso 1 1 calc R U . . .
C7 C 0.1447(4) 1.0953(3) 0.1178(3) 0.0462(6) Uani 1 1 d . . . . .
H7 H 0.149371 1.046861 0.175846 0.055 Uiso 1 1 calc R U . . .
C6 C 0.2170(3) 1.0598(3) 0.0429(3) 0.0387(8) Uani 1 1 d . . . . .
N1 N 0.1454(3) 0.5534(3) -0.0543(2) 0.0455(7) Uani 1 1 d . . . . .
N3 N 0.5429(3) 0.6851(3) -0.1577(2) 0.0400(7) Uani 1 1 d . . . . .
O1 O -0.0747(4) 1.0532(4) 0.2638(3) 0.0981(12) Uani 1 1 d . . . . .
H1 H -0.050387 0.987502 0.292229 0.147 Uiso 1 1 calc R U . . .
C9 C -0.2218(5) 1.0843(6) 0.2687(4) 0.0894(17) Uani 1 1 d . . . . .
H9A H -0.219265 1.100723 0.340225 0.134 Uiso 1 1 calc R U . . .
H9B H -0.293488 1.019055 0.242562 0.134 Uiso 1 1 calc R U . . .
H9C H -0.256313 1.155110 0.226955 0.134 Uiso 1 1 calc R U . . .
H4N H 0.013(4) 1.3435(19) 0.019(3) 0.063(12) Uiso 1 1 d D . . . .
H3N H 0.547(5) 0.741(4) -0.212(4) 0.103(17) Uiso 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 Fe1 C3 180.0 3_665 . ?
C3 Fe1 C2 91.58(12) 3_665 3_665 ?
C3 Fe1 C2 88.42(12) . 3_665 ?
C3 Fe1 C2 88.42(12) 3_665 . ?
C3 Fe1 C2 91.58(12) . . ?
C2 Fe1 C2 180.00(12) 3_665 . ?
C3 Fe1 C1 90.22(12) 3_665 3_665 ?
C3 Fe1 C1 89.78(12) . 3_665 ?
C2 Fe1 C1 90.63(12) 3_665 3_665 ?
C2 Fe1 C1 89.38(12) . 3_665 ?
C3 Fe1 C1 89.78(12) 3_665 . ?
C3 Fe1 C1 90.22(12) . . ?
C2 Fe1 C1 89.37(12) 3_665 . ?
C2 Fe1 C1 90.62(12) . . ?
C1 Fe1 C1 180.0 3_665 . ?
C4 N4 C8 122.3(3) . . ?
C4 N4 H4N 120(3) . . ?
C8 N4 H4N 118(3) . . ?
N3 C3 Fe1 178.0(3) . . ?
N4 C4 C5 119.9(4) . . ?
N4 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C1 Fe1 178.3(3) . . ?
N2 C2 Fe1 178.6(3) . . ?
N4 C8 C7 120.3(3) . . ?
N4 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C8 C7 C6 118.7(3) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 I1 118.8(3) . . ?
C5 C6 I1 121.7(3) . . ?
C3 N3 H3N 174(3) . . ?
C9 O1 H1 109.5 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
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
I1 C6 2.080(3) . ?
Fe1 C3 1.877(3) 3_665 ?
Fe1 C3 1.877(3) . ?
Fe1 C2 1.915(3) 3_665 ?
Fe1 C2 1.915(3) . ?
Fe1 C1 1.918(3) 3_665 ?
Fe1 C1 1.918(3) . ?
N4 C4 1.325(5) . ?
N4 C8 1.328(5) . ?
N4 H4N 0.893(10) . ?
C3 N3 1.151(4) . ?
C4 C5 1.360(5) . ?
C4 H4 0.9300 . ?
N2 C2 1.148(4) . ?
C1 N1 1.150(3) . ?
C8 C7 1.363(5) . ?
C8 H8 0.9300 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9300 . ?
C7 C6 1.379(5) . ?
C7 H7 0.9300 . ?
N3 H3N 0.96(5) . ?
O1 C9 1.362(5) . ?
O1 H1 0.8200 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
