#------------------------------------------------------------------------------
#$Date: 2020-12-10 04:27:11 +0100 (jue 10 de dic de 2020) $
#$Revision: 259727 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/17/7241705.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_7241705
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            'C26 H26 Cl2 Fe N10 O2'
_chemical_formula_weight         637.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 95.040(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7562(6)
_cell_length_b                   13.1732(10)
_cell_length_c                   12.6457(7)
_cell_measurement_reflns_used    1403
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      36.4044
_cell_measurement_theta_min      3.8000
_cell_volume                     1453.01(17)
_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)'
_computing_structure_solution
;
SHELXT (Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0886
_diffrn_reflns_av_unetI/netI     0.1451
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5298
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.986
_diffrn_reflns_theta_max         24.986
_diffrn_reflns_theta_min         3.877
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08615
_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            green
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.998
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2531
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      0.868
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0657
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0776P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1443
_refine_ls_wR_factor_ref         0.1551
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1273
_reflns_number_total             2531
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01359e2.cif
_cod_data_source_block           HCF_2ClPy
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7241705
_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Fe1 Fe 0.500000 0.500000 0.000000 0.0316(3) Uani 1 2 d S . P . .
Cl1 Cl 0.6705(2) 0.94673(18) 0.07133(15) 0.1018(7) Uani 1 1 d . . . . .
N3 N 0.2582(5) 0.3908(3) 0.1185(3) 0.0490(7) Uani 1 1 d . . . . .
N1 N 0.4869(5) 0.6850(4) 0.1475(3) 0.0490(7) Uani 1 1 d . . . . .
C3 C 0.3515(6) 0.4319(4) 0.0760(4) 0.0354(7) Uani 1 1 d . . . . .
N2 N 0.7693(5) 0.4086(3) 0.1353(3) 0.0490(7) Uani 1 1 d . . . . .
N4 N 0.8723(6) 0.8542(4) -0.0263(4) 0.0594(14) Uani 1 1 d . . . . .
C1 C 0.4931(5) 0.6136(4) 0.0938(4) 0.0354(7) Uani 1 1 d . . . . .
C9 C 0.1481(7) 0.6176(4) 0.2269(5) 0.0579(16) Uani 1 1 d . . . . .
H9 H 0.244903 0.591606 0.218181 0.069 Uiso 1 1 calc R U . . .
C10 C 0.0357(8) 0.6095(5) 0.1488(5) 0.0638(17) Uani 1 1 d . . . . .
H10 H 0.053978 0.578271 0.085209 0.077 Uiso 1 1 calc R U . . .
N5 N 0.1215(6) 0.6620(4) 0.3150(4) 0.0576(13) Uani 1 1 d . . . . .
H5N H 0.195019 0.665772 0.364635 0.069 Uiso 1 1 calc R U . . .
C2 C 0.6651(5) 0.4432(4) 0.0860(3) 0.0354(7) Uani 1 1 d . . . . .
C11 C -0.1061(7) 0.6474(4) 0.1630(5) 0.0589(16) Uani 1 1 d . . . . .
H11 H -0.186135 0.641209 0.109980 0.071 Uiso 1 1 calc R U . . .
C13 C -0.0128(7) 0.7020(5) 0.3328(5) 0.0596(16) Uani 1 1 d . . . . .
H13 H -0.026994 0.734300 0.396541 0.071 Uiso 1 1 calc R U . . .
C4 C 0.8542(7) 0.9051(5) 0.0578(5) 0.0594(16) Uani 1 1 d . . . . .
C5 C 0.9698(9) 0.9275(5) 0.1370(4) 0.075(2) Uani 1 1 d . . . . .
H5 H 0.951286 0.965023 0.196783 0.090 Uiso 1 1 calc R U . . .
C8 C 1.0147(9) 0.8215(6) -0.0370(5) 0.082(2) Uani 1 1 d . . . . .
H8 H 1.031962 0.785405 -0.098026 0.098 Uiso 1 1 calc R U . . .
C7 C 1.1352(9) 0.8377(5) 0.0357(6) 0.0793(18) Uani 1 1 d . U . . .
H7 H 1.231633 0.811909 0.025411 0.095 Uiso 1 1 calc R U . . .
C6 C 1.1131(9) 0.8908(5) 0.1215(6) 0.0782(18) Uani 1 1 d . U . . .
H6 H 1.194911 0.903561 0.171750 0.094 Uiso 1 1 calc R U . . .
C12 C -0.1281(7) 0.6942(5) 0.2555(5) 0.0629(17) Uani 1 1 d . . . . .
H12 H -0.223721 0.721214 0.265825 0.075 Uiso 1 1 calc R U . . .
O1 O 0.0228(4) 0.3563(3) 0.2375(3) 0.0492(10) Uani 1 1 d D . . . .
H1 H 0.119(2) 0.372(4) 0.204(3) 0.11(3) Uiso 1 1 d D . . . .
H3 H 0.022(7) 0.316(3) 0.304(2) 0.20(4) Uiso 1 1 d D . . . .
H2 H -0.074(2) 0.373(4) 0.193(3) 0.100 Uiso 1 1 d D 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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 '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'
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
C2 Fe1 C2 180.0 3_665 . ?
C2 Fe1 C3 92.57(19) 3_665 3_665 ?
C2 Fe1 C3 87.4(2) . 3_665 ?
C2 Fe1 C3 87.4(2) 3_665 . ?
C2 Fe1 C3 92.57(19) . . ?
C3 Fe1 C3 180.0 3_665 . ?
C2 Fe1 C1 91.0(2) 3_665 3_665 ?
C2 Fe1 C1 89.0(2) . 3_665 ?
C3 Fe1 C1 89.7(2) 3_665 3_665 ?
C3 Fe1 C1 90.3(2) . 3_665 ?
C2 Fe1 C1 89.0(2) 3_665 . ?
C2 Fe1 C1 91.0(2) . . ?
C3 Fe1 C1 90.3(2) 3_665 . ?
C3 Fe1 C1 89.7(2) . . ?
C1 Fe1 C1 180.0 3_665 . ?
N3 C3 Fe1 177.5(4) . . ?
C4 N4 C8 116.0(6) . . ?
N1 C1 Fe1 177.4(4) . . ?
N5 C9 C10 119.7(6) . . ?
N5 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 119.5(6) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C9 N5 C13 123.6(5) . . ?
C9 N5 H5N 118.2 . . ?
C13 N5 H5N 118.2 . . ?
N2 C2 Fe1 177.4(4) . . ?
C12 C11 C10 118.8(6) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
N5 C13 C12 117.8(6) . . ?
N5 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
N4 C4 C5 125.0(6) . . ?
N4 C4 Cl1 115.8(5) . . ?
C5 C4 Cl1 119.2(5) . . ?
C6 C5 C4 116.1(6) . . ?
C6 C5 H5 122.0 . . ?
C4 C5 H5 122.0 . . ?
N4 C8 C7 123.9(6) . . ?
N4 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
C6 C7 C8 118.7(7) . . ?
C6 C7 H7 120.7 . . ?
C8 C7 H7 120.7 . . ?
C7 C6 C5 120.3(7) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C13 C12 C11 120.6(6) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
H1 O1 H3 123(3) . . ?
H1 O1 H2 115(3) . . ?
H3 O1 H2 121(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
Fe1 C2 1.886(5) 3_665 ?
Fe1 C2 1.886(5) . ?
Fe1 C3 1.907(5) 3_665 ?
Fe1 C3 1.907(5) . ?
Fe1 C1 1.913(5) 3_665 ?
Fe1 C1 1.913(5) . ?
Cl1 C4 1.722(7) . ?
N3 C3 1.151(5) . ?
N1 C1 1.165(6) . ?
N2 C2 1.153(6) . ?
N4 C4 1.279(7) . ?
N4 C8 1.336(8) . ?
C9 N5 1.298(6) . ?
C9 C10 1.336(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(8) . ?
C10 H10 0.9300 . ?
N5 C13 1.325(7) . ?
N5 H5N 0.8600 . ?
C11 C12 1.350(8) . ?
C11 H11 0.9300 . ?
C13 C12 1.346(8) . ?
C13 H13 0.9300 . ?
C4 C5 1.392(8) . ?
C5 C6 1.374(9) . ?
C5 H5 0.9300 . ?
C8 C7 1.355(9) . ?
C8 H8 0.9300 . ?
C7 C6 1.319(9) . ?
C7 H7 0.9300 . ?
C6 H6 0.9300 . ?
C12 H12 0.9300 . ?
O1 H1 1.0003(11) . ?
O1 H3 1.0003(10) . ?
O1 H2 1.0003(10) . ?
