#------------------------------------------------------------------------------
#$Date: 2024-04-05 02:07:11 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290888 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/82/7248216.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_7248216
loop_
_publ_author_name
'Lozančić, Ana'
'Burazer, Sanja'
'Renka, Sanja'
'Molčanov, Krešimir'
'Molčanov, Lidija'
'Jurić, Marijana'
_publ_section_title
;
 Proton transport in oxalate compounds of iron(iii) containing
 (alkyl)ammonium cations: the influence of the density of hydrogen bonds
 on conductivity
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              1892
_journal_page_last               1901
_journal_paper_doi               10.1039/D3CE01267K
_journal_volume                  26
_journal_year                    2024
_chemical_formula_sum            'C9 H18 Cl2 Fe N O4'
_chemical_formula_weight         330.99
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-03-25T12:08:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2022-06-09 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.469(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2146(5)
_cell_length_b                   8.5542(3)
_cell_length_c                   15.9856(7)
_cell_measurement_reflns_used    5837
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.218
_cell_measurement_theta_min      4.213
_cell_volume                     1445.85(11)
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.051
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.97
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10979
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.97
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.202
_diffrn_reflns_theta_min         4.232
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    11.810
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.25335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_description       prism
_exptl_crystal_F_000             1105
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3063
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0733
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0681P)²+10.6631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1934
_reflns_number_gt                2581
_reflns_number_total             3063
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce01267k2.cif
_cod_data_source_block           marijana_spoj5_100k_auto
_cod_depositor_comments
'Adding full bibliography for 7248214--7248217.cif.'
_cod_original_cell_volume        1445.84(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7248216
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Fe1 0.38010(8) 0.24995(9) 0.04427(6) 0.0288(3) Uani d 1 . . Fe
Cl1A 0.18001(14) 0.1652(2) -0.01236(12) 0.0446(4) Uani d 0.903(3) A 1 Cl
Cl2A 0.38083(15) 0.33362(19) 0.17898(11) 0.0406(4) Uani d 0.903(3) A 1 Cl
O1A 0.4239(4) 0.1555(5) -0.0660(3) 0.0330(9) Uani d 0.903(3) A 1 O
O2A 0.4729(4) 0.0470(5) 0.0976(3) 0.0325(9) Uani d 0.903(3) A 1 O
O3A 0.5655(4) 0.3435(5) 0.0685(3) 0.0327(9) Uani d 0.903(3) A 1 O
O4A 0.3408(4) 0.4535(5) -0.0264(3) 0.0335(9) Uani d 0.903(3) A 1 O
C1A 0.4860(6) 0.0313(7) -0.0471(4) 0.0280(12) Uani d 0.903(3) A 1 C
C2A 0.5648(5) 0.4692(7) 0.0274(4) 0.0291(12) Uani d 0.903(3) A 1 C
Cl1B 0.1729(12) 0.3327(16) -0.0303(10) 0.037(3) Uani d 0.097(3) A 2 Cl
Cl2B 0.3563(15) 0.1674(18) 0.1651(10) 0.042(4) Uani d 0.097(3) A 2 Cl
O1B 0.339(4) 0.046(5) -0.039(3) 0.0330(9) Uani d 0.097(3) A 2 O
O2B 0.557(4) 0.155(4) 0.070(2) 0.0325(9) Uani d 0.097(3) A 2 O
O3B 0.463(3) 0.455(5) 0.095(3) 0.0327(9) Uani d 0.097(3) A 2 O
O4B 0.427(3) 0.340(5) -0.071(3) 0.0335(9) Uani d 0.097(3) A 2 O
C1B 0.444(5) -0.020(7) -0.030(4) 0.0280(12) Uani d 0.097(3) A 2 C
C2B 0.509(5) 0.528(7) 0.044(4) 0.0291(12) Uani d 0.097(3) A 2 C
N1 0.9603(5) 0.3043(7) 0.1781(4) 0.0490(13) Uani d 1 . . N
C3 0.8542(5) 0.2735(8) 0.2161(4) 0.0395(14) Uani d 1 . . C
H3A 0.876948 0.324515 0.274905 0.047 Uiso calc 1 . . H
H3B 0.776342 0.324454 0.176986 0.047 Uiso calc 1 . . H
C4 0.8255(6) 0.1085(9) 0.2264(5) 0.0517(17) Uani d 1 . . C
H4A 0.756511 0.101843 0.251092 0.078 Uiso calc 1 . . H
H4B 0.799911 0.056759 0.168416 0.078 Uiso calc 1 . . H
H4C 0.900816 0.05682 0.266628 0.078 Uiso calc 1 . . H
C5A 1.0754(13) 0.2159(18) 0.2117(9) 0.047(4) Uani d 0.515(18) B 1 C
H5A1 1.132714 0.24053 0.177922 0.056 Uiso calc 0.515(18) B 1 H
H5A2 1.057099 0.102425 0.206749 0.056 Uiso calc 0.515(18) B 1 H
C6A 1.1363(12) 0.2635(18) 0.3097(10) 0.046(4) Uani d 0.515(18) B 1 C
H6A1 1.215662 0.206054 0.335866 0.069 Uiso calc 0.515(18) B 1 H
H6A2 1.153597 0.376043 0.31345 0.069 Uiso calc 0.515(18) B 1 H
H6A3 1.078371 0.238647 0.342129 0.069 Uiso calc 0.515(18) B 1 H
C5B 0.9692(14) 0.2078(19) 0.1078(10) 0.051(4) Uani d 0.485(18) B 2 C
H5B1 0.972322 0.096106 0.124558 0.062 Uiso calc 0.485(18) B 2 H
H5B2 1.046358 0.233296 0.093481 0.062 Uiso calc 0.485(18) B 2 H
C6B 0.8521(15) 0.2413(16) 0.0292(10) 0.044(4) Uani d 0.485(18) B 2 C
H6B1 0.853376 0.177492 -0.021464 0.066 Uiso calc 0.485(18) B 2 H
H6B2 0.776694 0.215757 0.044454 0.066 Uiso calc 0.485(18) B 2 H
H6B3 0.850339 0.352223 0.013541 0.066 Uiso calc 0.485(18) B 2 H
C7 0.9699(6) 0.4816(8) 0.1725(4) 0.0438(14) Uani d 1 . . C
H7A 0.888064 0.522323 0.132613 0.053 Uiso calc 1 . . H
H7B 0.984214 0.526336 0.232157 0.053 Uiso calc 1 . . H
C8 1.0729(7) 0.5374(9) 0.1395(5) 0.0582(18) Uani d 1 . . C
H8A 1.072678 0.651974 0.137876 0.087 Uiso calc 1 . . H
H8B 1.154778 0.500463 0.179431 0.087 Uiso calc 1 . . H
H8C 1.058462 0.496443 0.079716 0.087 Uiso calc 1 . . H
C9A 0.9047(16) 0.2536(17) 0.0793(9) 0.044(4) Uani d 0.515(18) B 1 C
H9A1 0.824911 0.308897 0.050797 0.065 Uiso calc 0.515(18) B 1 H
H9A2 0.964835 0.279182 0.048817 0.065 Uiso calc 0.515(18) B 1 H
H9A3 0.889194 0.140616 0.076086 0.065 Uiso calc 0.515(18) B 1 H
C9B 1.0827(12) 0.2574(17) 0.2580(14) 0.050(6) Uani d 0.485(18) B . C
H9B1 1.085931 0.318082 0.310729 0.075 Uiso calc 0.485(18) . . H
H9B2 1.079706 0.145665 0.270639 0.075 Uiso calc 0.485(18) . . H
H9B3 1.15819 0.279512 0.242115 0.075 Uiso calc 0.485(18) . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 '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
O3B Fe1 O2B 88.7(15) . . ?
O4A Fe1 O2A 159.21(17) . . ?
O4A Fe1 O3A 78.40(15) . . ?
O2A Fe1 O3A 85.04(16) . . ?
O4A Fe1 O1A 86.15(17) . . ?
O2A Fe1 O1A 78.43(16) . . ?
O3A Fe1 O1A 79.30(17) . . ?
O3B Fe1 Cl2B 95.8(12) . . ?
O2B Fe1 Cl2B 95.2(11) . . ?
O3B Fe1 O1B 158.0(15) . . ?
O2B Fe1 O1B 78.2(15) . . ?
Cl2B Fe1 O1B 102.8(11) . . ?
O3B Fe1 O4B 80.1(15) . . ?
O2B Fe1 O4B 79.7(14) . . ?
Cl2B Fe1 O4B 173.5(10) . . ?
O1B Fe1 O4B 80.2(14) . . ?
O4A Fe1 Cl1A 92.86(12) . . ?
O2A Fe1 Cl1A 101.21(13) . . ?
O3A Fe1 Cl1A 167.32(13) . . ?
O1A Fe1 Cl1A 91.07(13) . . ?
O4A Fe1 Cl2A 100.84(14) . . ?
O2A Fe1 Cl2A 91.81(12) . . ?
O3A Fe1 Cl2A 90.83(13) . . ?
O1A Fe1 Cl2A 166.60(12) . . ?
Cl1A Fe1 Cl2A 99.90(7) . . ?
O3B Fe1 Cl1B 101.0(11) . . ?
O2B Fe1 Cl1B 161.8(11) . . ?
Cl2B Fe1 Cl1B 99.0(5) . . ?
O1B Fe1 Cl1B 87.6(11) . . ?
O4B Fe1 Cl1B 86.7(10) . . ?
C1A O1A Fe1 112.6(4) . . ?
C1A O2A Fe1 115.4(4) 3_655 . ?
C2A O3A Fe1 112.9(3) . . ?
C2A O4A Fe1 115.5(4) 3_665 . ?
O1A C1A O2A 126.5(6) . 3_655 ?
O1A C1A C1A 116.8(6) . 3_655 ?
O2A C1A C1A 116.7(6) 3_655 3_655 ?
O4A C2A O3A 126.8(5) 3_665 . ?
O4A C2A C2A 117.3(6) 3_665 3_665 ?
O3A C2A C2A 115.8(6) . 3_665 ?
C1B O1B Fe1 107(4) . . ?
C1B O2B Fe1 114(4) 3_655 . ?
C2B O3B Fe1 113(4) . . ?
C2B O4B Fe1 106(3) 3_665 . ?
O3B C2B C2B 121(6) . 3_665 ?
O4B C2B C2B 119(6) 3_665 3_665 ?
C5B N1 C7 120.3(9) . . ?
C5A N1 C7 118.3(8) . . ?
C5B N1 C3 118.8(8) . . ?
C5A N1 C3 118.8(8) . . ?
C7 N1 C3 105.9(5) . . ?
C5A N1 C9A 103.8(9) . . ?
C7 N1 C9A 103.3(7) . . ?
C3 N1 C9A 104.7(7) . . ?
C5B N1 C9B 102.7(10) . . ?
C5A N1 C9B 30.2(7) . . ?
C7 N1 C9B 103.9(7) . . ?
C3 N1 C9B 102.5(7) . . ?
C9A N1 C9B 134.1(10) . . ?
C4 C3 N1 116.1(5) . . ?
C4 C3 H3A 108.3 . . ?
N1 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
N1 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5A C6A 106.2(9) . . ?
N1 C5A H5A1 110.5 . . ?
C6A C5A H5A1 110.5 . . ?
N1 C5A H5A2 110.5 . . ?
C6A C5A H5A2 110.5 . . ?
H5A1 C5A H5A2 108.7 . . ?
C5A C6A H6A1 109.5 . . ?
C5A C6A H6A2 109.5 . . ?
H6A1 C6A H6A2 109.5 . . ?
C5A C6A H6A3 109.5 . . ?
H6A1 C6A H6A3 109.5 . . ?
H6A2 C6A H6A3 109.5 . . ?
N1 C5B C6B 106.1(10) . . ?
N1 C5B H5B1 110.5 . . ?
C6B C5B H5B1 110.5 . . ?
N1 C5B H5B2 110.5 . . ?
C6B C5B H5B2 110.5 . . ?
H5B1 C5B H5B2 108.7 . . ?
C5B C6B H6B1 109.5 . . ?
C5B C6B H6B2 109.5 . . ?
H6B1 C6B H6B2 109.5 . . ?
C5B C6B H6B3 109.5 . . ?
H6B1 C6B H6B3 109.5 . . ?
H6B2 C6B H6B3 109.5 . . ?
C8 C7 N1 114.5(5) . . ?
C8 C7 H7A 108.6 . . ?
N1 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
N1 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9A H9A1 109.5 . . ?
N1 C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
N1 C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
N1 C9B H9B1 109.5 . . ?
N1 C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
N1 C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Fe1 O3B . 2.02(4) ?
Fe1 O4A . 2.042(4) ?
Fe1 O2B . 2.05(4) ?
Fe1 O2A . 2.057(4) ?
Fe1 O3A . 2.140(4) ?
Fe1 O1A . 2.139(4) ?
Fe1 Cl2B . 2.155(13) ?
Fe1 O1B . 2.15(4) ?
Fe1 O4B . 2.22(4) ?
Fe1 Cl1A . 2.2420(17) ?
Fe1 Cl2A . 2.2666(17) ?
Fe1 Cl1B . 2.340(14) ?
O1A C1A . 1.251(7) ?
O2A C1A 3_655 1.250(7) ?
O3A C2A . 1.258(7) ?
O4A C2A 3_665 1.253(7) ?
C1A C1A 3_655 1.529(12) ?
C2A C2A 3_665 1.521(11) ?
O1B C1B . 1.27(7) ?
O2B C1B 3_655 1.32(7) ?
O3B C2B . 1.27(7) ?
O4B C2B 3_665 1.33(7) ?
C1B C1B 3_655 1.35(12) ?
C2B C2B 3_665 1.42(11) ?
N1 C5B . 1.425(13) ?
N1 C5A . 1.436(13) ?
N1 C7 . 1.525(9) ?
N1 C3 . 1.528(7) ?
N1 C9A . 1.554(13) ?
N1 C9B . 1.583(15) ?
C3 C4 . 1.469(9) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 H4A . 0.98 ?
C4 H4B . 0.98 ?
C4 H4C . 0.98 ?
C5A C6A . 1.541(15) ?
C5A H5A1 . 0.99 ?
C5A H5A2 . 0.99 ?
C6A H6A1 . 0.98 ?
C6A H6A2 . 0.98 ?
C6A H6A3 . 0.98 ?
C5B C6B . 1.512(16) ?
C5B H5B1 . 0.99 ?
C5B H5B2 . 0.99 ?
C6B H6B1 . 0.98 ?
C6B H6B2 . 0.98 ?
C6B H6B3 . 0.98 ?
C7 C8 . 1.498(9) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C9A H9A1 . 0.98 ?
C9A H9A2 . 0.98 ?
C9A H9A3 . 0.98 ?
C9B H9B1 . 0.98 ?
C9B H9B2 . 0.98 ?
C9B H9B3 . 0.98 ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 O1A C1A O2A -178.1(5) . . . 3_655 ?
Fe1 O1A C1A C1A 2.1(9) . . . 3_655 ?
Fe1 O3A C2A O4A -177.1(5) . . . 3_665 ?
Fe1 O3A C2A C2A 1.9(8) . . . 3_665 ?
Fe1 O1B C1B O2B 175(4) . . . 3_655 ?
Fe1 O1B C1B C1B 9(10) . . . 3_655 ?
Fe1 O3B C2B O4B -176(4) . . . 3_665 ?
Fe1 O3B C2B C2B 4(8) . . . 3_665 ?
C5B N1 C3 C4 39.9(11) . . . . ?
C5A N1 C3 C4 -45.0(10) . . . . ?
C7 N1 C3 C4 179.0(5) . . . . ?
C9A N1 C3 C4 70.2(9) . . . . ?
C9B N1 C3 C4 -72.4(9) . . . . ?
C7 N1 C5A C6A 65.5(13) . . . . ?
C3 N1 C5A C6A -65.2(14) . . . . ?
C9A N1 C5A C6A 179.2(11) . . . . ?
C9B N1 C5A C6A -2.2(13) . . . . ?
C7 N1 C5B C6B -67.4(13) . . . . ?
C3 N1 C5B C6B 65.7(14) . . . . ?
C9B N1 C5B C6B 177.9(11) . . . . ?
C5B N1 C7 C8 -43.8(10) . . . . ?
C5A N1 C7 C8 41.6(10) . . . . ?
C3 N1 C7 C8 177.9(5) . . . . ?
C9A N1 C7 C8 -72.4(9) . . . . ?
C9B N1 C7 C8 70.3(9) . . . . ?
