#------------------------------------------------------------------------------
#$Date: 2020-12-10 05:27:11 +0200 (Thu, 10 Dec 2020) $
#$Revision: 259727 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/17/7241710.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_7241710
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            'C16 H16 Br2 Fe N8 O2'
_chemical_formula_weight         568.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/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                 108.439(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7058(15)
_cell_length_b                   8.3867(6)
_cell_length_c                   18.3571(18)
_cell_measurement_reflns_used    2392
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.4060
_cell_measurement_theta_min      4.8820
_cell_volume                     2147.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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 0.987
_diffrn_measured_fraction_theta_max 0.982
_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  0.0313
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7901
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         4.670
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.452
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0055(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0309
_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)+(0.0352P)²+1.5024P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0767
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1932
_reflns_number_total             2302
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01359e2.cif
_cod_data_source_block           HCF_3BrPy
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7241710
_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.
;
_exptl_absorpt_special_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.66611(5) 0.750000 0.02394(15) Uani 1 2 d S T P . .
Br1 Br 0.01790(2) 0.25941(4) 0.49891(2) 0.06028(16) Uani 1 1 d . . . . .
O1 O 0.70168(13) 0.1506(2) 0.66103(11) 0.0395(4) Uani 1 1 d D . . . .
N1 N 0.36935(16) 0.6613(3) 0.58288(12) 0.0432(5) Uani 1 1 d . . . . .
N4 N 0.24284(15) 0.4970(3) 0.46956(13) 0.0371(5) Uani 1 1 d . . . . .
H4N H 0.283413 0.565945 0.495685 0.044 Uiso 1 1 calc R U . . .
C2 C 0.42245(16) 0.5047(3) 0.77575(13) 0.0276(5) Uani 1 1 d . . . . .
N3 N 0.62108(18) 0.9147(3) 0.70712(14) 0.0490(6) Uani 1 1 d D . . . .
N2 N 0.37574(16) 0.4096(3) 0.79206(13) 0.0420(5) Uani 1 1 d . . . . .
C1 C 0.41840(17) 0.6635(3) 0.64555(13) 0.0287(5) Uani 1 1 d . . . . .
C3 C 0.57471(18) 0.8212(3) 0.72379(13) 0.0315(5) Uani 1 1 d D . . . .
C5 C 0.10994(19) 0.3354(3) 0.45639(14) 0.0366(6) Uani 1 1 d . . . . .
C4 C 0.17445(18) 0.4466(3) 0.49686(14) 0.0374(6) Uani 1 1 d . . . . .
H4 H 0.170328 0.486480 0.542990 0.045 Uiso 1 1 calc R U . . .
C8 C 0.2513(2) 0.4455(4) 0.40374(16) 0.0445(7) Uani 1 1 d . . . . .
H8 H 0.300189 0.483854 0.386465 0.053 Uiso 1 1 calc R U . . .
C6 C 0.1157(2) 0.2794(3) 0.38773(16) 0.0472(7) Uani 1 1 d . . . . .
H6 H 0.071909 0.204865 0.359390 0.057 Uiso 1 1 calc R U . . .
C7 C 0.1879(2) 0.3361(4) 0.36163(15) 0.0518(8) Uani 1 1 d . . . . .
H7 H 0.193223 0.299522 0.315322 0.062 Uiso 1 1 calc R U . . .
H3N H 0.656(2) 0.999(3) 0.688(2) 0.092(13) Uiso 1 1 d D . . . .
H1V H 0.7702(3) 0.142(5) 0.677(2) 0.083(12) Uiso 1 1 d D . . . .
H2V H 0.682(3) 0.250(2) 0.677(2) 0.069(11) Uiso 1 1 d 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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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 91.36(15) . 2_656 ?
C3 Fe1 C1 89.05(10) . . ?
C3 Fe1 C1 91.88(10) 2_656 . ?
C3 Fe1 C1 91.88(10) . 2_656 ?
C3 Fe1 C1 89.05(10) 2_656 2_656 ?
C1 Fe1 C1 178.67(15) . 2_656 ?
C3 Fe1 C2 179.24(10) . . ?
C3 Fe1 C2 89.08(10) 2_656 . ?
C1 Fe1 C2 90.31(10) . . ?
C1 Fe1 C2 88.75(10) 2_656 . ?
C3 Fe1 C2 89.07(10) . 2_656 ?
C3 Fe1 C2 179.24(10) 2_656 2_656 ?
C1 Fe1 C2 88.75(10) . 2_656 ?
C1 Fe1 C2 90.31(10) 2_656 2_656 ?
C2 Fe1 C2 90.50(13) . 2_656 ?
H1V O1 H2V 111(3) . . ?
C8 N4 C4 122.8(2) . . ?
C8 N4 H4N 118.6 . . ?
C4 N4 H4N 118.6 . . ?
N2 C2 Fe1 178.9(2) . . ?
C3 N3 H3N 175(2) . . ?
N1 C1 Fe1 179.8(2) . . ?
N3 C3 Fe1 179.0(2) . . ?
C4 C5 C6 119.8(3) . . ?
C4 C5 Br1 118.22(19) . . ?
C6 C5 Br1 121.9(2) . . ?
N4 C4 C5 119.3(2) . . ?
N4 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N4 C8 C7 119.5(3) . . ?
N4 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C5 C6 C7 118.6(3) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
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 C3 1.861(3) . ?
Fe1 C3 1.861(3) 2_656 ?
Fe1 C1 1.914(2) . ?
Fe1 C1 1.914(2) 2_656 ?
Fe1 C2 1.923(2) . ?
Fe1 C2 1.923(2) 2_656 ?
Br1 C5 1.875(3) . ?
O1 H1V 0.959(2) . ?
O1 H2V 0.960(2) . ?
N1 C1 1.149(3) . ?
N4 C8 1.325(4) . ?
N4 C4 1.327(3) . ?
N4 H4N 0.8600 . ?
C2 N2 1.152(3) . ?
N3 C3 1.143(3) . ?
N3 H3N 0.997(10) . ?
C5 C4 1.370(4) . ?
C5 C6 1.372(4) . ?
C4 H4 0.9300 . ?
C8 C7 1.362(4) . ?
C8 H8 0.9300 . ?
C6 C7 1.380(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
