# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_marijana_zuco_nh4_29
_database_code_depnum_ccdc_archive 'CCDC 2178037'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-06-09 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;

_audit_creation_date             2022-03-14T12:46:14-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C2 H12 Cl3 Fe N2 O6'
_chemical_formula_moiety         'C2 H2 Cl3 Fe O5, H2 O, 2(H4 N)'
_chemical_formula_weight         322.34

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/m'
_symmetry_space_group_name_Hall  '-P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,1/2+y,-z
3 -x,-y,-z
4 x,1/2-y,z

_cell_length_a                   9.0027(3)
_cell_length_b                   7.5270(2)
_cell_length_c                   9.0306(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.109(5)
_cell_angle_gamma                90
_cell_volume                     558.56(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2710
_cell_measurement_theta_min      5.368
_cell_measurement_theta_max      75.614
_cell_measurement_temperature    293(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_F_000             326
_exptl_absorpt_coefficient_mu    17.573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.0047
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            3912
_diffrn_reflns_av_R_equivalents  0.0848
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_theta_min         5.366
_diffrn_reflns_theta_max         75.793
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   difmap

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             1249
_reflns_number_gt                1154
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.079
_refine_ls_wR_factor_ref         0.2251
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.166
_refine_ls_number_reflns         1249
_refine_ls_number_parameters     92
_refine_ls_number_restraints     17
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1706P)²+0.0193P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         1.665
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.214
_refine_ls_extinction_method     none
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'
Fe Fe -1.1336 3.1974 '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'

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.32848(10) 0.25 0.78524(10) 0.0287(4) Uani d 1 . . Fe
Cl1 0.16753(15) 0.01293(18) 0.79689(15) 0.0448(5) Uani d 1 . . Cl
Cl2 0.2118(2) 0.25 0.50127(19) 0.0501(6) Uani d 1 . . Cl
O1 0.5094(4) 0.0777(5) 0.7992(4) 0.0366(8) Uani d 1 . . O
O2 0.7600(5) 0.0687(7) 0.8052(6) 0.0561(12) Uani d 1 . . O
O3 0.4316(7) 0.25 1.0402(6) 0.0450(12) Uani d 1 . . O
H3A 0.475(8) 0.161(8) 1.118(8) 0.067 Uiso d 1 . . H
C1 0.6410(5) 0.1495(7) 0.8022(5) 0.0363(11) Uani d 1 . . C
N1 0.9326(7) -0.25 0.9229(8) 0.0415(13) Uani d 1 . . N
H1A 1.004(8) -0.25 0.870(9) 0.062 Uiso d 1 . . H
H1B 0.999(8) -0.25 1.034(3) 0.062 Uiso d 1 . . H
H1C 0.875(6) -0.142(5) 0.894(7) 0.062 Uiso d 1 . . H
N2 0.4819(10) -0.25 0.5780(11) 0.084(4) Uani d 1 . . N
H2A 0.546(8) -0.150(8) 0.631(9) 0.126 Uiso d 1 . . H
H2B 0.461(15) -0.25 0.468(4) 0.126 Uiso d 1 . . H
H2C 0.384(8) -0.25 0.590(15) 0.126 Uiso d 1 . . H
O4 0.8517(9) 0.25 0.5307(10) 0.085(3) Uani d 1 . . O
H4A 0.975041 0.25 0.620296 0.127 Uiso d 1 . . H
H4B 0.802(6) 0.25 0.606(6) 0.127 Uiso d 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O1 . 2.045(3) ?
Fe1 O3 . 2.102(5) ?
Fe1 Cl1 . 2.3280(13) ?
Fe1 Cl2 . 2.3407(18) ?
O1 C1 . 1.293(6) ?
O2 C1 . 1.222(6) ?
O3 H3A . 0.93(2) ?
N1 H1A . 0.941(19) ?
N1 H1B . 0.94(2) ?
N1 H1C . 0.939(19) ?
N2 H2A . 0.950(19) ?
N2 H2B . 0.93(2) ?
N2 H2C . 0.93(2) ?
O4 H4A . 1.074(7) ?
O4 H4B . 0.95(2) ?

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
O1 Fe1 O3 87.02(17) . . ?
O1 Fe1 Cl1 90.35(10) . . ?
O3 Fe1 Cl1 87.43(12) . . ?
O1 Fe1 Cl2 93.28(11) . . ?
O3 Fe1 Cl2 179.61(17) . . ?
Cl1 Fe1 Cl2 92.32(5) . . ?
C1 O1 Fe1 115.9(3) . . ?
Fe1 O3 H3A 133(5) . . ?
O2 C1 O1 125.4(5) . . ?
H1A N1 H1B 106(4) . . ?
H1A N1 H1C 106(3) . . ?
H1B N1 H1C 110(4) . . ?
H2A N2 H2B 111(4) . . ?
H2A N2 H2C 110(4) . . ?
H2B N2 H2C 110(5) . . ?
H4A O4 H4B 96(4) . . ?

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 O1 C1 O2 -177.6(4) . . . . ?
Fe1 O1 C1 C1 2.6(3) . . . 4_565 ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_marijana_zuco3_100k
_database_code_depnum_ccdc_archive 'CCDC 2178038'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-06-09 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;

_audit_creation_date             2022-03-24T11:27:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_moiety         'C2 Cl2 Fe O4, C4 H12 N, H2 O'
_chemical_formula_sum            'C6 H14 Cl2 Fe N O5'
_chemical_formula_weight         306.93

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   7.4880(3)
_cell_length_b                   8.5970(4)
_cell_length_c                   9.8960(3)
_cell_angle_alpha                90.603(3)
_cell_angle_beta                 99.679(3)
_cell_angle_gamma                95.105(3)
_cell_volume                     625.28(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5694
_cell_measurement_theta_min      5.154
_cell_measurement_theta_max      75.492
_cell_measurement_temperature    100(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.63
_exptl_crystal_F_000             314
_exptl_absorpt_coefficient_mu    13.665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.26522
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Ruby, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4323
_diffrn_reflns_number            8586
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_theta_min         5.167
_diffrn_reflns_theta_max         76.308
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.97
_diffrn_reflns_Laue_measured_fraction_full 0.97
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.97
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   mixed

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             2503
_reflns_number_gt                2302
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0621
_refine_ls_wR_factor_ref         0.2126
_refine_ls_goodness_of_fit_ref   1.448
_refine_ls_restrained_S_all      1.447
_refine_ls_number_reflns         2503
_refine_ls_number_parameters     142
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1073P)²+0.5628P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.227
_refine_diff_density_min         -1.003
_refine_diff_density_rms         0.186
_refine_ls_extinction_method     none
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'
Fe Fe -1.1336 3.1974 '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'

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.11788(9) 0.26052(9) 1.16438(7) 0.0152(3) Uani d 1 . . Fe
Cl1 0.03952(15) 0.35350(16) 1.35660(11) 0.0227(3) Uani d 1 . . Cl
Cl2 0.40047(14) 0.19917(15) 1.24945(11) 0.0207(3) Uani d 1 . . Cl
O1 -0.1250(4) 0.3361(5) 1.0491(3) 0.0210(8) Uani d 1 . . O
O2 0.2143(4) 0.4695(4) 1.0884(3) 0.0170(7) Uani d 1 . . O
O3 0.1328(4) 0.1650(4) 0.9648(3) 0.0186(7) Uani d 1 . . O
O4 0.0260(4) -0.0491(5) 0.8336(3) 0.0211(8) Uani d 1 . . O
C1 0.0984(6) 0.5365(7) 1.0117(4) 0.0203(11) Uani d 1 . . C
C2 0.0473(6) 0.0358(6) 0.9422(5) 0.0177(10) Uani d 1 . . C
N1 0.5749(6) 0.7317(5) 0.2993(4) 0.0200(9) Uani d 1 . . N
H1 0.517141 0.760612 0.207805 0.024 Uiso calc 1 . . H
C3 0.6951(7) 0.6072(7) 0.2809(6) 0.0275(12) Uani d 1 . . C
H3A 0.788919 0.647681 0.232152 0.041 Uiso calc 1 . . H
H3B 0.749357 0.572745 0.369055 0.041 Uiso calc 1 . . H
H3C 0.624543 0.520671 0.229586 0.041 Uiso calc 1 . . H
C4 0.6825(7) 0.8763(7) 0.3682(5) 0.0265(12) Uani d 1 . . C
H4A 0.601301 0.954279 0.378546 0.04 Uiso calc 1 . . H
H4B 0.745093 0.850621 0.456761 0.04 Uiso calc 1 . . H
H4C 0.769375 0.915887 0.312996 0.04 Uiso calc 1 . . H
C5 0.4268(7) 0.6728(7) 0.3749(5) 0.0242(11) Uani d 1 . . C
H5A 0.477303 0.667112 0.471479 0.029 Uiso calc 1 . . H
H5B 0.381473 0.567753 0.341606 0.029 Uiso calc 1 . . H
C6 0.2694(8) 0.7734(8) 0.3600(6) 0.0332(14) Uani d 1 . . C
H6A 0.179383 0.729547 0.410723 0.05 Uiso calc 1 . . H
H6B 0.312452 0.877063 0.394878 0.05 Uiso calc 1 . . H
H6C 0.216553 0.777633 0.264911 0.05 Uiso calc 1 . . H
O5 0.5579(5) 0.1556(6) 0.9536(4) 0.0298(10) Uani d 1 . . O
H5C 0.656(6) 0.211(8) 1.012(6) 0.045 Uiso d 1 . . H
H5D 0.476(7) 0.125(9) 1.014(6) 0.045 Uiso d 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O4 2_557 2.031(4) ?
Fe1 O2 . 2.072(4) ?
Fe1 O1 . 2.136(3) ?
Fe1 O3 . 2.154(3) ?
Fe1 Cl1 . 2.2424(13) ?
Fe1 Cl2 . 2.2524(12) ?
O1 C1 2_567 1.271(7) ?
O2 C1 . 1.240(6) ?
O3 C2 . 1.231(6) ?
O4 C2 . 1.272(6) ?
C1 C1 2_567 1.528(9) ?
C2 C2 2_557 1.548(9) ?
N1 C3 . 1.487(7) ?
N1 C5 . 1.495(6) ?
N1 C4 . 1.509(7) ?
C5 C6 . 1.511(8) ?

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
O4 Fe1 O2 158.74(14) 2_557 . ?
O4 Fe1 O1 86.01(15) 2_557 . ?
O2 Fe1 O1 78.30(14) . . ?
O4 Fe1 O3 78.45(14) 2_557 . ?
O2 Fe1 O3 84.72(14) . . ?
O1 Fe1 O3 79.99(14) . . ?
O4 Fe1 Cl1 95.27(11) 2_557 . ?
O2 Fe1 Cl1 98.80(11) . . ?
O1 Fe1 Cl1 89.46(11) . . ?
O3 Fe1 Cl1 168.02(10) . . ?
O4 Fe1 Cl2 100.74(11) 2_557 . ?
O2 Fe1 Cl2 92.61(10) . . ?
O1 Fe1 Cl2 168.19(11) . . ?
O3 Fe1 Cl2 91.78(10) . . ?
Cl1 Fe1 Cl2 99.46(5) . . ?
C1 O1 Fe1 113.3(3) 2_567 . ?
C1 O2 Fe1 114.9(3) . . ?
C2 O3 Fe1 112.5(3) . . ?
C2 O4 Fe1 116.8(3) . 2_557 ?
O2 C1 O1 126.5(4) . 2_567 ?
O2 C1 C1 118.2(6) . 2_567 ?
O1 C1 C1 115.3(5) 2_567 2_567 ?
O3 C2 O4 127.8(4) . . ?
O3 C2 C2 117.6(5) . 2_557 ?
O4 C2 C2 114.5(6) . 2_557 ?
C3 N1 C5 111.0(4) . . ?
C3 N1 C4 111.5(4) . . ?
C5 N1 C4 111.7(4) . . ?
N1 C5 C6 113.6(5) . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_marijana_spoj5_100k_auto
_database_code_depnum_ccdc_archive 'CCDC 2178039'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-06-09 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;

_audit_creation_date             2022-03-25T12:08:49-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C9 H18 Cl2 Fe N O4'
_chemical_formula_weight         330.99

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
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

_cell_length_a                   11.2146(5)
_cell_length_b                   8.5542(3)
_cell_length_c                   15.9856(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.469(4)
_cell_angle_gamma                90
_cell_volume                     1445.84(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5837
_cell_measurement_theta_min      4.213
_cell_measurement_theta_max      78.218
_cell_measurement_temperature    100(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             1105
_exptl_absorpt_coefficient_mu    11.810
_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_absorpt_correction_T_min  0.25335
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            10979
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.051
_diffrn_reflns_theta_min         4.232
_diffrn_reflns_theta_max         80.202
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.97
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.97
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             3063
_reflns_number_gt                2581
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0733
_refine_ls_wR_factor_ref         0.1934
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.031
_refine_ls_number_reflns         3063
_refine_ls_number_parameters     219
_refine_ls_number_restraints     44
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0681P)²+10.6631P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
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'

_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_cell_refinement       '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)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_marijana_30feoxcl_auto
_database_code_depnum_ccdc_archive 'CCDC 2178040'
loop_
_audit_author_name
_audit_author_address
'Kresimir Molcanov'
;Rudjer Boskovic Institute
Croatia
;
_audit_update_record             
;
2022-06-09 deposited with the CCDC.	2024-02-23 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_marijana_30feoxcl_auto 
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Very small and poorly diffracting crystal with disorder.
;
_vrf_PLAT020_marijana_30feoxcl_auto 
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.287 Report
RESPONSE: Very small and poorly diffracting crystal with disorder.
;
# Added during the CSD deposition process: Thursday 09 June 2022 09:57 AM
# end Validation Reply Form


_audit_creation_date             2022-03-25T11:42:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#==============================================================================

# CHEMICAL DATA

_chemical_formula_sum            'C9 H18 Cl2 Fe N O4'
_chemical_formula_weight         330.99

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
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

_cell_length_a                   11.2283(16)
_cell_length_b                   8.6109(9)
_cell_length_c                   16.306(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.460(19)
_cell_angle_gamma                90
_cell_volume                     1486.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2789
_cell_measurement_theta_min      4.236
_cell_measurement_theta_max      76.473
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             684
_exptl_absorpt_coefficient_mu    11.488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.4217
_exptl_absorpt_correction_T_max  1

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            18962
_diffrn_reflns_av_R_equivalents  0.2874
_diffrn_reflns_av_unetI/netI     0.2005
_diffrn_reflns_theta_min         4.208
_diffrn_reflns_theta_max         82.952
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

#==============================================================================

# STRUCTURE SOLUTION

_atom_sites_solution_hydrogens   geom

#==============================================================================

# REFINEMENT DATA

_reflns_number_total             3167
_reflns_number_gt                1459
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2281
_refine_ls_R_factor_gt           0.153
_refine_ls_wR_factor_ref         0.4212
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_restrained_S_all      1.21
_refine_ls_number_reflns         3167
_refine_ls_number_parameters     154
_refine_ls_number_restraints     61
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.837
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.242
_refine_ls_extinction_method     none
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'

_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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 0.88301(15) 0.75050(16) 0.04439(13) 0.0746(7) Uani d 1 . . Fe
Cl1 0.6844(3) 0.8402(4) -0.0086(3) 0.1241(15) Uani d 1 . . Cl
Cl2 0.8834(4) 0.6644(4) 0.1743(3) 0.1181(14) Uani d 1 . . Cl
O1 1.0685(6) 0.6551(8) 0.0652(5) 0.082(2) Uani d 1 . . O
O2 0.8411(6) 0.5495(9) -0.0268(6) 0.089(2) Uani d 1 . . O
O3 0.9227(6) 0.8476(8) -0.0651(5) 0.0779(19) Uani d 1 . . O
O4 0.9788(7) 0.9512(8) 0.0960(5) 0.085(2) Uani d 1 . . O
C1 1.0653(9) 0.5311(11) 0.0269(8) 0.070(3) Uani d 1 . . C
C2 0.9841(10) 0.9706(10) -0.0462(7) 0.070(3) Uani d 1 . . C
N1 0.4643(11) 0.6961(14) 0.1817(9) 0.107(3) Uani d 1 . . N
C3 0.579(2) 0.772(2) 0.2145(17) 0.153(6) Uani d 1 . . C
H3A 0.567549 0.883858 0.209609 0.184 Uiso calc 1 . . H
H3B 0.635421 0.741435 0.18327 0.184 Uiso calc 1 . . H
C4 0.630(2) 0.726(2) 0.3047(16) 0.175(10) Uani d 1 . . C
H4A 0.710812 0.775565 0.331305 0.262 Uiso calc 1 . . H
H4B 0.573534 0.757123 0.334513 0.262 Uiso calc 1 . . H
H4C 0.640999 0.615553 0.308332 0.262 Uiso calc 1 . . H
C5 0.4711(13) 0.5205(18) 0.1734(11) 0.119(4) Uani d 1 . . C
H5A 0.485395 0.4746 0.230179 0.143 Uiso calc 1 . . H
H5B 0.389889 0.483781 0.135229 0.143 Uiso calc 1 . . H
C6 0.5695(19) 0.464(2) 0.1398(15) 0.179(8) Uani d 1 . . C
H6A 0.566678 0.352781 0.136747 0.269 Uiso calc 1 . . H
H6B 0.555117 0.505982 0.082698 0.269 Uiso calc 1 . . H
H6C 0.65083 0.496781 0.177854 0.269 Uiso calc 1 . . H
C7 0.3608(14) 0.7221(16) 0.2169(10) 0.109(4) Uani d 1 . . C
H7A 0.286683 0.668748 0.179156 0.131 Uiso calc 1 . . H
H7B 0.384074 0.671863 0.273272 0.131 Uiso calc 1 . . H
C8 0.3238(14) 0.8814(18) 0.2276(12) 0.141(6) Uani d 1 . . C
H8A 0.255736 0.88022 0.250961 0.211 Uiso calc 1 . . H
H8B 0.39454 0.935931 0.266807 0.211 Uiso calc 1 . . H
H8C 0.296666 0.932801 0.172224 0.211 Uiso calc 1 . . H
C9 0.428(3) 0.767(2) 0.0836(17) 0.169(8) Uani d 1 . . C
H9A 0.347626 0.726854 0.048202 0.253 Uiso calc 1 . . H
H9B 0.42418 0.877952 0.085911 0.253 Uiso calc 1 . . H
H9C 0.491477 0.736964 0.059033 0.253 Uiso calc 1 . . H



#==============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O2 . 2.049(8) ?
Fe1 O4 . 2.061(7) ?
Fe1 O3 . 2.149(7) ?
Fe1 O1 . 2.158(7) ?
Fe1 Cl2 . 2.243(4) ?
Fe1 Cl1 . 2.244(4) ?
O1 C1 . 1.232(11) ?
O2 C1 3_765 1.259(10) ?
O3 C2 . 1.245(10) ?
O4 C2 3_775 1.230(10) ?
C1 C1 3_765 1.53(2) ?
C2 C2 3_775 1.51(2) ?
N1 C3 . 1.39(2) ?
N1 C7 . 1.474(16) ?
N1 C5 . 1.523(19) ?
N1 C9 . 1.63(2) ?
C3 C4 . 1.445(17) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
C4 H4A . 0.96 ?
C4 H4B . 0.96 ?
C4 H4C . 0.96 ?
C5 C6 . 1.469(14) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C6 H6A . 0.96 ?
C6 H6B . 0.96 ?
C6 H6C . 0.96 ?
C7 C8 . 1.461(15) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C8 H8A . 0.96 ?
C8 H8B . 0.96 ?
C8 H8C . 0.96 ?
C9 H9A . 0.96 ?
C9 H9B . 0.96 ?
C9 H9C . 0.96 ?

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
O2 Fe1 O4 158.3(3) . . ?
O2 Fe1 O3 86.0(3) . . ?
O4 Fe1 O3 77.8(3) . . ?
O2 Fe1 O1 78.2(3) . . ?
O4 Fe1 O1 84.8(3) . . ?
O3 Fe1 O1 79.8(3) . . ?
O2 Fe1 Cl2 100.6(3) . . ?
O4 Fe1 Cl2 93.1(2) . . ?
O3 Fe1 Cl2 167.9(2) . . ?
O1 Fe1 Cl2 91.6(2) . . ?
O2 Fe1 Cl1 93.5(2) . . ?
O4 Fe1 Cl1 100.7(3) . . ?
O3 Fe1 Cl1 90.0(2) . . ?
O1 Fe1 Cl1 167.2(3) . . ?
Cl2 Fe1 Cl1 99.56(16) . . ?
C1 O1 Fe1 112.7(6) . . ?
C1 O2 Fe1 115.6(7) 3_765 . ?
C2 O3 Fe1 112.1(6) . . ?
C2 O4 Fe1 115.8(6) 3_775 . ?
O1 C1 O2 126.5(10) . 3_765 ?
O1 C1 C1 116.9(10) . 3_765 ?
O2 C1 C1 116.5(11) 3_765 3_765 ?
O4 C2 O3 125.7(10) 3_775 . ?
O4 C2 C2 117.0(9) 3_775 3_775 ?
O3 C2 C2 117.3(10) . 3_775 ?
C3 N1 C7 122.1(16) . . ?
C3 N1 C5 115.8(13) . . ?
C7 N1 C5 104.8(9) . . ?
C3 N1 C9 95.6(14) . . ?
C7 N1 C9 110.7(13) . . ?
C5 N1 C9 106.6(13) . . ?
N1 C3 C4 105.5(15) . . ?
N1 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
N1 C3 H3B 110.7 . . ?
C4 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
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 . . ?
C6 C5 N1 115.3(13) . . ?
C6 C5 H5A 108.4 . . ?
N1 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
N1 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N1 118.8(13) . . ?
C8 C7 H7A 107.6 . . ?
N1 C7 H7A 107.6 . . ?
C8 C7 H7B 107.6 . . ?
N1 C7 H7B 107.6 . . ?
H7A C7 H7B 107 . . ?
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 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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 O1 C1 O2 179.4(9) . . . 3_765 ?
Fe1 O1 C1 C1 0.0(15) . . . 3_765 ?
Fe1 O3 C2 O4 178.8(9) . . . 3_775 ?
Fe1 O3 C2 C2 -1.4(14) . . . 3_775 ?
C7 N1 C3 C4 61(2) . . . . ?
C5 N1 C3 C4 -69(2) . . . . ?
C9 N1 C3 C4 179.6(19) . . . . ?
C3 N1 C5 C6 -42(2) . . . . ?
C7 N1 C5 C6 -179.5(16) . . . . ?
C9 N1 C5 C6 63(2) . . . . ?
C3 N1 C7 C8 50(2) . . . . ?
C5 N1 C7 C8 -176.1(15) . . . . ?
C9 N1 C7 C8 -62(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3B Cl2 0.97 2.91 3.80(2) 152.6 . yes
C3 H3A Cl2 0.97 3 3.79(2) 138.9 2_655 yes
C5 H5B O2 0.97 2.62 3.576(17) 167.3 3_665 yes
C7 H7A O1 0.97 2.54 3.437(17) 154.4 1_455 yes
C9 H9C Cl1 0.96 2.88 3.72(2) 146.5 . yes
C9 H9B Cl1 0.96 2.82 3.677(17) 149.4 3_675 yes
C3 H3B Cl2 0.97 2.91 3.80(2) 152.6 . yes
C3 H3A Cl2 0.97 3 3.79(2) 138.9 2_655 yes
C5 H5B O2 0.97 2.62 3.576(17) 167.3 3_665 yes
C7 H7A O1 0.97 2.54 3.437(17) 154.4 1_455 yes
C9 H9C Cl1 0.96 2.88 3.72(2) 146.5 . yes
C9 H9B Cl1 0.96 2.82 3.677(17) 149.4 3_675 yes



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
