# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_me200606Fe1
_database_code_depnum_ccdc_archive 'CCDC 2053757'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka' 'University of Pardubice'
_audit_update_record             
;
2021-08-25 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 Fe N2 P'
_chemical_formula_weight         312.12

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'
Fe Fe 0.3463 0.8444 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   7.3267(5)
_cell_length_b                   10.2286(7)
_cell_length_c                   18.5961(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.660(2)
_cell_angle_gamma                90
_cell_volume                     1393.53(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    31521
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.511
_exptl_crystal_size_mid          0.327
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.183
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5165
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.693
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            31521
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.1080
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.272
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3219
_reflns_number_gt                2451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0256P)²+0.8244P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3219
_refine_ls_number_parameters     178
_refine_ls_number_restraints     240
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0667
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.53902(4) 0.18795(3) 0.62304(2) 0.02184(10) Uani 1 1 d . U . . .
H1 H -0.045(3) 0.617(2) 0.5125(13) 0.030(7) Uiso 1 1 d . . . . .
P1 P 0.06087(10) 0.77977(6) 0.58297(4) 0.03692(18) Uani 1 1 d . U . . .
N1 N 0.0301(3) 0.63699(18) 0.54227(11) 0.0264(4) Uani 1 1 d . U . . .
C1 C 0.3867(3) 0.3545(2) 0.60780(11) 0.0179(4) Uani 1 1 d . U . . .
N2 N 0.1405(2) 0.53621(16) 0.56184(9) 0.0219(4) Uani 1 1 d . U . . .
C2 C 0.2735(3) 0.2468(2) 0.62735(13) 0.0252(5) Uani 1 1 d . U . . .
H2 H 0.1940 0.2425 0.6707 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2935(3) 0.1467(2) 0.57543(14) 0.0358(6) Uani 1 1 d . U . . .
H3 H 0.2304 0.0600 0.5757 0.043 Uiso 1 1 calc R U . . .
C4 C 0.4190(3) 0.1903(2) 0.52337(13) 0.0353(6) Uani 1 1 d . U . . .
H4 H 0.4601 0.1402 0.4803 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3985(3) 0.4857(2) 0.64520(11) 0.0218(5) Uani 1 1 d . U . . .
C5 C 0.4769(3) 0.3181(2) 0.54342(11) 0.0250(5) Uani 1 1 d . U . . .
H5 H 0.5667 0.3730 0.5169 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5892(3) 0.5459(2) 0.63540(13) 0.0351(6) Uani 1 1 d . U . . .
H9A H 0.6139 0.5554 0.5840 0.053 Uiso 1 1 calc R U . . .
H9B H 0.6814 0.4888 0.6575 0.053 Uiso 1 1 calc R U . . .
H9C H 0.5937 0.6320 0.6585 0.053 Uiso 1 1 calc R U . . .
C8 C 0.2340(4) 0.7099(2) 0.63151(13) 0.0332(6) Uani 1 1 d . U . . .
H8 H 0.3057 0.7542 0.6667 0.040 Uiso 1 1 calc R U . . .
C7 C 0.2563(3) 0.5782(2) 0.61257(11) 0.0210(4) Uani 1 1 d . U . . .
C10 C 0.3605(4) 0.4725(3) 0.72606(12) 0.0404(7) Uani 1 1 d . U . . .
H10A H 0.2361 0.4398 0.7328 0.061 Uiso 1 1 calc R U . . .
H10B H 0.3733 0.5581 0.7492 0.061 Uiso 1 1 calc R U . . .
H10C H 0.4479 0.4111 0.7477 0.061 Uiso 1 1 calc R U . . .
C11 C 0.7208(3) 0.2190(2) 0.70541(13) 0.0349(6) Uani 1 1 d . U . . .
H11 H 0.7273 0.2989 0.7363 0.042 Uiso 1 1 calc R U . . .
C12 C 0.6156(3) 0.1065(2) 0.71929(13) 0.0348(6) Uani 1 1 d . U . . .
H12 H 0.5354 0.0919 0.7617 0.042 Uiso 1 1 calc R U . . .
C13 C 0.6460(4) 0.0174(3) 0.66230(15) 0.0443(7) Uani 1 1 d . U . . .
H13 H 0.5897 -0.0712 0.6573 0.053 Uiso 1 1 calc R U . . .
C14 C 0.7666(4) 0.0755(3) 0.61353(15) 0.0510(8) Uani 1 1 d . U . . .
H14 H 0.8116 0.0350 0.5681 0.061 Uiso 1 1 calc R U . . .
C15 C 0.8135(3) 0.2004(3) 0.63966(15) 0.0458(7) Uani 1 1 d . U . . .
H15 H 0.8980 0.2640 0.6164 0.055 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C15 2.035(2) . ?
Fe1 C14 2.035(2) . ?
Fe1 C5 2.039(2) . ?
Fe1 C2 2.039(2) . ?
Fe1 C3 2.040(2) . ?
Fe1 C4 2.043(2) . ?
Fe1 C11 2.043(2) . ?
Fe1 C13 2.043(2) . ?
Fe1 C12 2.047(2) . ?
Fe1 C1 2.054(2) . ?
P1 N1 1.659(2) . ?
P1 C8 1.705(2) . ?
N1 N2 1.358(2) . ?
N1 H1 0.80(2) . ?
C1 C5 1.424(3) . ?
C1 C2 1.429(3) . ?
C1 C6 1.514(3) . ?
N2 C7 1.333(3) . ?
C2 C3 1.416(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.415(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.422(3) . ?
C4 H4 1.0000 . ?
C6 C7 1.528(3) . ?
C6 C10 1.538(3) . ?
C6 C9 1.540(3) . ?
C5 H5 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 C7 1.402(3) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.410(3) . ?
C11 C15 1.418(4) . ?
C11 H11 1.0000 . ?
C12 C13 1.417(4) . ?
C12 H12 1.0000 . ?
C13 C14 1.406(4) . ?
C13 H13 1.0000 . ?
C14 C15 1.408(4) . ?
C14 H14 1.0000 . ?
C15 H15 1.0000 . ?

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
C15 Fe1 C14 40.47(12) . . ?
C15 Fe1 C5 106.35(10) . . ?
C14 Fe1 C5 118.83(11) . . ?
C15 Fe1 C2 156.53(11) . . ?
C14 Fe1 C2 162.44(12) . . ?
C5 Fe1 C2 68.32(9) . . ?
C15 Fe1 C3 160.70(12) . . ?
C14 Fe1 C3 124.39(12) . . ?
C5 Fe1 C3 68.37(10) . . ?
C2 Fe1 C3 40.62(9) . . ?
C15 Fe1 C4 123.47(11) . . ?
C14 Fe1 C4 105.82(11) . . ?
C5 Fe1 C4 40.79(9) . . ?
C2 Fe1 C4 68.35(10) . . ?
C3 Fe1 C4 40.56(11) . . ?
C15 Fe1 C11 40.71(11) . . ?
C14 Fe1 C11 67.99(11) . . ?
C5 Fe1 C11 125.54(10) . . ?
C2 Fe1 C11 122.60(10) . . ?
C3 Fe1 C11 157.15(11) . . ?
C4 Fe1 C11 161.57(11) . . ?
C15 Fe1 C13 67.97(12) . . ?
C14 Fe1 C13 40.32(12) . . ?
C5 Fe1 C13 153.94(10) . . ?
C2 Fe1 C13 126.87(11) . . ?
C3 Fe1 C13 108.13(10) . . ?
C4 Fe1 C13 119.59(10) . . ?
C11 Fe1 C13 67.71(10) . . ?
C15 Fe1 C12 68.43(11) . . ?
C14 Fe1 C12 68.25(11) . . ?
C5 Fe1 C12 163.26(10) . . ?
C2 Fe1 C12 109.74(10) . . ?
C3 Fe1 C12 121.78(11) . . ?
C4 Fe1 C12 155.39(10) . . ?
C11 Fe1 C12 40.35(10) . . ?
C13 Fe1 C12 40.53(10) . . ?
C15 Fe1 C1 120.23(11) . . ?
C14 Fe1 C1 154.29(12) . . ?
C5 Fe1 C1 40.70(8) . . ?
C2 Fe1 C1 40.85(8) . . ?
C3 Fe1 C1 68.69(8) . . ?
C4 Fe1 C1 68.73(9) . . ?
C11 Fe1 C1 108.85(9) . . ?
C13 Fe1 C1 164.25(11) . . ?
C12 Fe1 C1 126.96(9) . . ?
N1 P1 C8 88.21(10) . . ?
N2 N1 P1 117.94(15) . . ?
N2 N1 H1 113.1(18) . . ?
P1 N1 H1 128.9(18) . . ?
C5 C1 C2 106.80(19) . . ?
C5 C1 C6 126.41(19) . . ?
C2 C1 C6 126.65(19) . . ?
C5 C1 Fe1 69.06(12) . . ?
C2 C1 Fe1 69.00(12) . . ?
C6 C1 Fe1 130.07(13) . . ?
C7 N2 N1 108.53(17) . . ?
C3 C2 C1 108.6(2) . . ?
C3 C2 Fe1 69.72(13) . . ?
C1 C2 Fe1 70.15(12) . . ?
C3 C2 H2 125.7 . . ?
C1 C2 H2 125.7 . . ?
Fe1 C2 H2 125.7 . . ?
C4 C3 C2 108.2(2) . . ?
C4 C3 Fe1 69.82(13) . . ?
C2 C3 Fe1 69.65(12) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 125.9 . . ?
C3 C4 C5 107.7(2) . . ?
C3 C4 Fe1 69.62(13) . . ?
C5 C4 Fe1 69.46(12) . . ?
C3 C4 H4 126.1 . . ?
C5 C4 H4 126.1 . . ?
Fe1 C4 H4 126.1 . . ?
C1 C6 C7 109.37(16) . . ?
C1 C6 C10 111.19(18) . . ?
C7 C6 C10 108.21(18) . . ?
C1 C6 C9 110.34(18) . . ?
C7 C6 C9 108.69(18) . . ?
C10 C6 C9 108.98(19) . . ?
C4 C5 C1 108.7(2) . . ?
C4 C5 Fe1 69.75(13) . . ?
C1 C5 Fe1 70.23(12) . . ?
C4 C5 H5 125.6 . . ?
C1 C5 H5 125.6 . . ?
Fe1 C5 H5 125.6 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C8 P1 110.98(17) . . ?
C7 C8 H8 124.5 . . ?
P1 C8 H8 124.5 . . ?
N2 C7 C8 114.34(19) . . ?
N2 C7 C6 120.48(18) . . ?
C8 C7 C6 125.19(19) . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C15 108.5(2) . . ?
C12 C11 Fe1 69.98(13) . . ?
C15 C11 Fe1 69.35(14) . . ?
C12 C11 H11 125.8 . . ?
C15 C11 H11 125.8 . . ?
Fe1 C11 H11 125.8 . . ?
C11 C12 C13 107.3(2) . . ?
C11 C12 Fe1 69.67(13) . . ?
C13 C12 Fe1 69.61(13) . . ?
C11 C12 H12 126.4 . . ?
C13 C12 H12 126.4 . . ?
Fe1 C12 H12 126.4 . . ?
C14 C13 C12 108.4(3) . . ?
C14 C13 Fe1 69.52(14) . . ?
C12 C13 Fe1 69.86(13) . . ?
C14 C13 H13 125.8 . . ?
C12 C13 H13 125.8 . . ?
Fe1 C13 H13 125.8 . . ?
C13 C14 C15 108.3(3) . . ?
C13 C14 Fe1 70.16(15) . . ?
C15 C14 Fe1 69.76(14) . . ?
C13 C14 H14 125.9 . . ?
C15 C14 H14 125.9 . . ?
Fe1 C14 H14 125.9 . . ?
C14 C15 C11 107.6(3) . . ?
C14 C15 Fe1 69.77(15) . . ?
C11 C15 Fe1 69.93(13) . . ?
C14 C15 H15 126.2 . . ?
C11 C15 H15 126.2 . . ?
Fe1 C15 H15 126.2 . . ?

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
N1 H1 N2 0.80(2) 2.20(2) 2.897(3) 146(2) 3_566

_refine_diff_density_max         0.312
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_me190729Fe1
_database_code_depnum_ccdc_archive 'CCDC 2053758'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice, Faculty of Chemical Technology, Pardubice
Czech Republic
;
_audit_update_record             
;
2021-01-04 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H36 Fe2 N2'
_chemical_formula_weight         536.31

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'
Fe Fe 0.3463 0.8444 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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'

_cell_length_a                   7.5627(10)
_cell_length_b                   10.1352(14)
_cell_length_c                   16.263(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.888(5)
_cell_angle_gamma                90
_cell_volume                     1231.6(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9897
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      28.62

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.204
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    1.200
_shelx_estimated_absorpt_T_min   0.549
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6166
_exptl_absorpt_correction_T_max  0.7677
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.803
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            29953
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.1276
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.376
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2937
_reflns_number_gt                2560
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2018.1-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1329P)²+9.6423P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2937
_refine_ls_number_parameters     158
_refine_ls_number_restraints     225
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0835
_refine_ls_wR_factor_ref         0.2450
_refine_ls_wR_factor_gt          0.2367
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.25559(12) 0.39811(10) 0.72547(5) 0.0125(3) Uani 1 1 d . . . . .
N1 N 0.4266(8) 0.0346(6) 0.5124(4) 0.0235(13) Uani 1 1 d . . . . .
C1 C 0.3668(8) 0.2740(6) 0.6470(4) 0.0110(10) Uani 1 1 d . . . . .
C2 C 0.3211(9) 0.2039(6) 0.7177(4) 0.0188(12) Uani 1 1 d . . . . .
H2A H 0.236006 0.128052 0.715547 0.023 Uiso 1 1 calc R U . . .
C3 C 0.4175(10) 0.2605(7) 0.7913(4) 0.0238(14) Uani 1 1 d . . . . .
H3A H 0.410509 0.231358 0.849401 0.029 Uiso 1 1 calc R U . . .
C4 C 0.5200(9) 0.3678(7) 0.7689(4) 0.0199(13) Uani 1 1 d . . . . .
H4A H 0.599917 0.426336 0.807867 0.024 Uiso 1 1 calc R U . . .
C5 C 0.4900(8) 0.3750(6) 0.6791(4) 0.0144(11) Uani 1 1 d . . . . .
H5A H 0.544298 0.441533 0.645009 0.017 Uiso 1 1 calc R U . . .
C6 C 0.3080(9) 0.2383(7) 0.5560(4) 0.0200(13) Uani 1 1 d . . . . .
C7 C 0.4578(8) 0.1565(7) 0.5284(4) 0.0160(12) Uani 1 1 d . . . . .
C8 C 0.2728(12) 0.3629(9) 0.5036(5) 0.0349(19) Uani 1 1 d . . . . .
H8A H 0.381088 0.417441 0.510551 0.052 Uiso 1 1 calc R U . . .
H8B H 0.174641 0.412608 0.521748 0.052 Uiso 1 1 calc R U . . .
H8C H 0.240211 0.338661 0.444900 0.052 Uiso 1 1 calc R U . . .
C9 C 0.1318(10) 0.1572(9) 0.5476(5) 0.0328(19) Uani 1 1 d . . . . .
H9A H 0.153420 0.074761 0.578958 0.049 Uiso 1 1 calc R U . . .
H9B H 0.090884 0.137146 0.488756 0.049 Uiso 1 1 calc R U . . .
H9C H 0.039971 0.208676 0.569648 0.049 Uiso 1 1 calc R U . . .
C10 C 0.6331(9) 0.2232(7) 0.5211(5) 0.0229(14) Uani 1 1 d . . . . .
H10A H 0.699787 0.169415 0.486238 0.034 Uiso 1 1 calc R U . . .
H10B H 0.703702 0.233025 0.576566 0.034 Uiso 1 1 calc R U . . .
H10C H 0.609686 0.310365 0.495688 0.034 Uiso 1 1 calc R U . . .
C11 C 0.0059(10) 0.4602(8) 0.6731(6) 0.0322(16) Uani 1 1 d . . . . .
H11A H -0.064462 0.425304 0.620510 0.039 Uiso 1 1 calc R U . . .
C12 C -0.0003(11) 0.4113(8) 0.7540(6) 0.0305(15) Uani 1 1 d . U . . .
H12A H -0.075505 0.336465 0.768876 0.037 Uiso 1 1 calc R U . . .
C13 C 0.1220(10) 0.4879(7) 0.8103(5) 0.0254(14) Uani 1 1 d . . . . .
H13A H 0.147527 0.476302 0.872078 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2022(10) 0.5832(6) 0.7634(5) 0.0217(13) Uani 1 1 d . . . . .
H14A H 0.293289 0.650305 0.786618 0.026 Uiso 1 1 calc R U . . .
C15 C 0.1312(11) 0.5673(7) 0.6788(5) 0.0252(14) Uani 1 1 d . . . . .
H15A H 0.162250 0.620811 0.631395 0.030 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C14 2.034(7) . ?
Fe1 C4 2.038(7) . ?
Fe1 C2 2.038(6) . ?
Fe1 C15 2.044(7) . ?
Fe1 C5 2.045(6) . ?
Fe1 C13 2.045(7) . ?
Fe1 C3 2.046(7) . ?
Fe1 C11 2.047(8) . ?
Fe1 C1 2.062(6) . ?
Fe1 C12 2.063(8) . ?
N1 C7 1.276(9) . ?
N1 N1 1.423(11) 3_656 ?
C1 C5 1.429(8) . ?
C1 C2 1.439(8) . ?
C1 C6 1.521(8) . ?
C2 C3 1.422(10) . ?
C2 H2A 1.0000 . ?
C3 C4 1.415(11) . ?
C3 H3A 1.0000 . ?
C4 C5 1.445(9) . ?
C4 H4A 1.0000 . ?
C5 H5A 1.0000 . ?
C6 C8 1.523(11) . ?
C6 C7 1.526(9) . ?
C6 C9 1.553(10) . ?
C7 C10 1.509(9) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.413(13) . ?
C11 C15 1.434(12) . ?
C11 H11A 1.0000 . ?
C12 C13 1.427(12) . ?
C12 H12A 1.0000 . ?
C13 C14 1.424(10) . ?
C13 H13A 1.0000 . ?
C14 C15 1.406(11) . ?
C14 H14A 1.0000 . ?
C15 H15A 1.0000 . ?

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
C14 Fe1 C4 105.3(3) . . ?
C14 Fe1 C2 166.1(3) . . ?
C4 Fe1 C2 69.0(3) . . ?
C14 Fe1 C15 40.3(3) . . ?
C4 Fe1 C15 128.7(3) . . ?
C2 Fe1 C15 152.8(3) . . ?
C14 Fe1 C5 116.2(3) . . ?
C4 Fe1 C5 41.5(3) . . ?
C2 Fe1 C5 68.5(3) . . ?
C15 Fe1 C5 109.5(3) . . ?
C14 Fe1 C13 40.8(3) . . ?
C4 Fe1 C13 113.2(3) . . ?
C2 Fe1 C13 128.4(3) . . ?
C15 Fe1 C13 68.3(3) . . ?
C5 Fe1 C13 147.8(3) . . ?
C14 Fe1 C3 126.9(3) . . ?
C4 Fe1 C3 40.5(3) . . ?
C2 Fe1 C3 40.7(3) . . ?
C15 Fe1 C3 165.9(3) . . ?
C5 Fe1 C3 68.4(3) . . ?
C13 Fe1 C3 105.6(3) . . ?
C14 Fe1 C11 68.2(3) . . ?
C4 Fe1 C11 169.4(3) . . ?
C2 Fe1 C11 119.3(3) . . ?
C15 Fe1 C11 41.0(3) . . ?
C5 Fe1 C11 132.7(3) . . ?
C13 Fe1 C11 67.9(3) . . ?
C3 Fe1 C11 150.1(4) . . ?
C14 Fe1 C1 150.4(3) . . ?
C4 Fe1 C1 69.6(2) . . ?
C2 Fe1 C1 41.1(2) . . ?
C15 Fe1 C1 119.3(3) . . ?
C5 Fe1 C1 40.7(2) . . ?
C13 Fe1 C1 168.6(3) . . ?
C3 Fe1 C1 68.9(3) . . ?
C11 Fe1 C1 111.6(3) . . ?
C14 Fe1 C12 68.6(3) . . ?
C4 Fe1 C12 146.7(3) . . ?
C2 Fe1 C12 108.8(3) . . ?
C15 Fe1 C12 68.6(3) . . ?
C5 Fe1 C12 170.9(3) . . ?
C13 Fe1 C12 40.6(3) . . ?
C3 Fe1 C12 115.7(3) . . ?
C11 Fe1 C12 40.2(4) . . ?
C1 Fe1 C12 131.7(3) . . ?
C7 N1 N1 114.1(8) . 3_656 ?
C5 C1 C2 106.6(5) . . ?
C5 C1 C6 127.0(6) . . ?
C2 C1 C6 126.2(6) . . ?
C5 C1 Fe1 69.0(3) . . ?
C2 C1 Fe1 68.6(3) . . ?
C6 C1 Fe1 131.4(4) . . ?
C3 C2 C1 108.6(6) . . ?
C3 C2 Fe1 69.9(4) . . ?
C1 C2 Fe1 70.4(3) . . ?
C3 C2 H2A 125.7 . . ?
C1 C2 H2A 125.7 . . ?
Fe1 C2 H2A 125.7 . . ?
C4 C3 C2 108.9(6) . . ?
C4 C3 Fe1 69.5(4) . . ?
C2 C3 Fe1 69.3(4) . . ?
C4 C3 H3A 125.5 . . ?
C2 C3 H3A 125.5 . . ?
Fe1 C3 H3A 125.5 . . ?
C3 C4 C5 107.0(6) . . ?
C3 C4 Fe1 70.0(4) . . ?
C5 C4 Fe1 69.5(4) . . ?
C3 C4 H4A 126.5 . . ?
C5 C4 H4A 126.5 . . ?
Fe1 C4 H4A 126.5 . . ?
C1 C5 C4 109.0(6) . . ?
C1 C5 Fe1 70.3(3) . . ?
C4 C5 Fe1 69.0(4) . . ?
C1 C5 H5A 125.5 . . ?
C4 C5 H5A 125.5 . . ?
Fe1 C5 H5A 125.5 . . ?
C1 C6 C8 110.2(6) . . ?
C1 C6 C7 107.2(5) . . ?
C8 C6 C7 111.1(6) . . ?
C1 C6 C9 109.2(6) . . ?
C8 C6 C9 108.4(7) . . ?
C7 C6 C9 110.6(6) . . ?
N1 C7 C10 123.6(6) . . ?
N1 C7 C6 117.6(6) . . ?
C10 C7 C6 118.7(6) . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C15 108.8(7) . . ?
C12 C11 Fe1 70.5(5) . . ?
C15 C11 Fe1 69.4(4) . . ?
C12 C11 H11A 125.6 . . ?
C15 C11 H11A 125.6 . . ?
Fe1 C11 H11A 125.6 . . ?
C11 C12 C13 107.2(7) . . ?
C11 C12 Fe1 69.3(4) . . ?
C13 C12 Fe1 69.0(4) . . ?
C11 C12 H12A 126.4 . . ?
C13 C12 H12A 126.4 . . ?
Fe1 C12 H12A 126.4 . . ?
C14 C13 C12 108.2(7) . . ?
C14 C13 Fe1 69.2(4) . . ?
C12 C13 Fe1 70.3(4) . . ?
C14 C13 H13A 125.9 . . ?
C12 C13 H13A 125.9 . . ?
Fe1 C13 H13A 125.9 . . ?
C15 C14 C13 108.5(7) . . ?
C15 C14 Fe1 70.2(4) . . ?
C13 C14 Fe1 70.0(4) . . ?
C15 C14 H14A 125.8 . . ?
C13 C14 H14A 125.8 . . ?
Fe1 C14 H14A 125.8 . . ?
C14 C15 C11 107.4(7) . . ?
C14 C15 Fe1 69.5(4) . . ?
C11 C15 Fe1 69.6(4) . . ?
C14 C15 H15A 126.3 . . ?
C11 C15 H15A 126.3 . . ?
Fe1 C15 H15A 126.3 . . ?

_refine_diff_density_max         1.997
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.151


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
####################################################################### 
# 
# 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_me200615Fe1
_database_code_depnum_ccdc_archive 'CCDC 2053759'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice, Faculty of Chemical Technology, Pardubice
Czech Republic
;
_audit_update_record             
;
2021-01-04 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 Fe N2 P'
_chemical_formula_weight         346.14

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'
Fe Fe 0.3463 0.8444 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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'

_cell_length_a                   19.1416(10)
_cell_length_b                   9.7740(6)
_cell_length_c                   8.2857(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.672(2)
_cell_angle_gamma                90
_cell_volume                     1545.02(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    35672
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.692
_exptl_crystal_size_mid          0.197
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    1.076
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5202
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.776
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            35672
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.135
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3555
_reflns_number_gt                2922
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0245P)²+3.3003P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3555
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.12613(2) 0.51093(4) 0.20806(5) 0.01542(12) Uani 1 1 d . . . . .
H1 H 0.560(2) 0.522(4) 0.952(5) 0.045(12) Uiso 1 1 d . . . . .
P1 P 0.59287(4) 0.62654(10) 0.72028(12) 0.0325(2) Uani 1 1 d . . . . .
C1 C 0.17243(15) 0.6161(3) 0.4026(3) 0.0175(6) Uani 1 1 d . . . . .
N1 N 0.54502(14) 0.5539(3) 0.8565(4) 0.0292(6) Uani 1 1 d . . . . .
C2 C 0.14532(16) 0.7087(3) 0.2781(3) 0.0202(6) Uani 1 1 d . . . . .
H2 H 0.173424 0.776684 0.220545 0.024 Uiso 1 1 calc R U . . .
N2 N 0.47442(13) 0.5461(3) 0.8214(3) 0.0249(6) Uani 1 1 d . . . . .
C3 C 0.07208(16) 0.6867(3) 0.2496(4) 0.0233(6) Uani 1 1 d . . . . .
H3 H 0.039781 0.736261 0.168588 0.028 Uiso 1 1 calc R U . . .
C5 C 0.11447(15) 0.5361(3) 0.4481(3) 0.0210(6) Uani 1 1 d . . . . .
H5 H 0.116807 0.461909 0.531518 0.025 Uiso 1 1 calc R U . . .
C4 C 0.05281(15) 0.5802(3) 0.3539(4) 0.0234(6) Uani 1 1 d . . . . .
H4 H 0.004568 0.542279 0.359669 0.028 Uiso 1 1 calc R U . . .
C7 C 0.26754(15) 0.5137(3) 0.5907(3) 0.0206(6) Uani 1 1 d . . . . .
H7 H 0.234675 0.450483 0.627675 0.025 Uiso 1 1 calc R U . . .
C6 C 0.24586(14) 0.6080(3) 0.4698(3) 0.0173(5) Uani 1 1 d . . . . .
C9 C 0.38605(15) 0.6032(3) 0.6068(3) 0.0194(6) Uani 1 1 d . . . . .
C8 C 0.33664(15) 0.5113(3) 0.6574(3) 0.0206(6) Uani 1 1 d . . . . .
H8 H 0.350349 0.445924 0.738720 0.025 Uiso 1 1 calc R U . . .
C10 C 0.36430(16) 0.6963(3) 0.4849(4) 0.0250(6) Uani 1 1 d . . . . .
H10 H 0.397053 0.759660 0.447716 0.030 Uiso 1 1 calc R U . . .
C11 C 0.29577(15) 0.6976(3) 0.4177(4) 0.0238(6) Uani 1 1 d . . . . .
H11 H 0.282485 0.761178 0.333975 0.029 Uiso 1 1 calc R U . . .
C12 C 0.45960(15) 0.6020(3) 0.6751(3) 0.0205(6) Uani 1 1 d . . . . .
C13 C 0.51771(16) 0.6529(4) 0.6014(4) 0.0296(7) Uani 1 1 d . . . . .
H13 H 0.515274 0.696404 0.498554 0.036 Uiso 1 1 calc R U . . .
C14 C 0.19929(18) 0.3796(4) 0.1319(4) 0.0351(8) Uani 1 1 d . . . . .
H14 H 0.247763 0.365892 0.183965 0.042 Uiso 1 1 calc R U . . .
C15 C 0.17926(19) 0.4752(3) 0.0086(4) 0.0339(8) Uani 1 1 d . . . . .
H15 H 0.211027 0.541031 -0.041801 0.041 Uiso 1 1 calc R U . . .
C16 C 0.1069(2) 0.4610(4) -0.0307(4) 0.0346(8) Uani 1 1 d . . . . .
H16 H 0.078219 0.515789 -0.113699 0.041 Uiso 1 1 calc R U . . .
C17 C 0.08156(18) 0.3579(4) 0.0669(4) 0.0337(8) Uani 1 1 d . . . . .
H17 H 0.031848 0.326134 0.065183 0.040 Uiso 1 1 calc R U . . .
C18 C 0.1388(2) 0.3072(3) 0.1686(4) 0.0354(8) Uani 1 1 d . . . . .
H18 H 0.136772 0.232795 0.251012 0.043 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C5 2.035(3) . ?
Fe1 C18 2.036(3) . ?
Fe1 C14 2.037(3) . ?
Fe1 C15 2.040(3) . ?
Fe1 C4 2.041(3) . ?
Fe1 C16 2.042(3) . ?
Fe1 C17 2.042(3) . ?
Fe1 C2 2.043(3) . ?
Fe1 C3 2.049(3) . ?
Fe1 C1 2.051(3) . ?
P1 N1 1.669(3) . ?
P1 C13 1.696(3) . ?
C1 C5 1.433(4) . ?
C1 C2 1.437(4) . ?
C1 C6 1.471(4) . ?
N1 N2 1.361(4) . ?
N1 H1 0.87(4) . ?
C2 C3 1.419(4) . ?
C2 H2 1.0000 . ?
N2 C12 1.339(4) . ?
C3 C4 1.420(4) . ?
C3 H3 1.0000 . ?
C5 C4 1.428(4) . ?
C5 H5 1.0000 . ?
C4 H4 1.0000 . ?
C7 C8 1.392(4) . ?
C7 C6 1.399(4) . ?
C7 H7 0.9500 . ?
C6 C11 1.391(4) . ?
C9 C8 1.393(4) . ?
C9 C10 1.398(4) . ?
C9 C12 1.474(4) . ?
C8 H8 0.9500 . ?
C10 C11 1.383(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.403(4) . ?
C13 H13 0.9500 . ?
C14 C18 1.412(5) . ?
C14 C15 1.414(5) . ?
C14 H14 1.0000 . ?
C15 C16 1.403(5) . ?
C15 H15 1.0000 . ?
C16 C17 1.404(5) . ?
C16 H16 1.0000 . ?
C17 C18 1.416(5) . ?
C17 H17 1.0000 . ?
C18 H18 1.0000 . ?

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
C5 Fe1 C18 107.40(13) . . ?
C5 Fe1 C14 120.80(14) . . ?
C18 Fe1 C14 40.56(15) . . ?
C5 Fe1 C15 156.12(14) . . ?
C18 Fe1 C15 68.21(14) . . ?
C14 Fe1 C15 40.58(15) . . ?
C5 Fe1 C4 41.01(11) . . ?
C18 Fe1 C4 121.08(14) . . ?
C14 Fe1 C4 156.31(14) . . ?
C15 Fe1 C4 161.59(14) . . ?
C5 Fe1 C16 161.96(14) . . ?
C18 Fe1 C16 67.99(14) . . ?
C14 Fe1 C16 67.87(14) . . ?
C15 Fe1 C16 40.20(15) . . ?
C4 Fe1 C16 125.10(14) . . ?
C5 Fe1 C17 125.07(13) . . ?
C18 Fe1 C17 40.65(15) . . ?
C14 Fe1 C17 68.10(14) . . ?
C15 Fe1 C17 67.86(14) . . ?
C4 Fe1 C17 107.87(13) . . ?
C16 Fe1 C17 40.20(14) . . ?
C5 Fe1 C2 68.86(12) . . ?
C18 Fe1 C2 161.85(14) . . ?
C14 Fe1 C2 124.88(14) . . ?
C15 Fe1 C2 107.60(13) . . ?
C4 Fe1 C2 68.53(12) . . ?
C16 Fe1 C2 121.02(13) . . ?
C17 Fe1 C2 155.89(14) . . ?
C5 Fe1 C3 68.73(12) . . ?
C18 Fe1 C3 156.27(14) . . ?
C14 Fe1 C3 161.71(15) . . ?
C15 Fe1 C3 124.86(13) . . ?
C4 Fe1 C3 40.64(12) . . ?
C16 Fe1 C3 108.04(13) . . ?
C17 Fe1 C3 121.14(13) . . ?
C2 Fe1 C3 40.58(12) . . ?
C5 Fe1 C1 41.05(11) . . ?
C18 Fe1 C1 124.52(13) . . ?
C14 Fe1 C1 107.16(13) . . ?
C15 Fe1 C1 120.69(13) . . ?
C4 Fe1 C1 69.04(11) . . ?
C16 Fe1 C1 155.97(14) . . ?
C17 Fe1 C1 161.93(13) . . ?
C2 Fe1 C1 41.11(11) . . ?
C3 Fe1 C1 68.88(11) . . ?
N1 P1 C13 88.35(15) . . ?
C5 C1 C2 106.9(2) . . ?
C5 C1 C6 127.4(3) . . ?
C2 C1 C6 125.7(3) . . ?
C5 C1 Fe1 68.86(16) . . ?
C2 C1 Fe1 69.16(15) . . ?
C6 C1 Fe1 127.50(19) . . ?
N2 N1 P1 118.0(2) . . ?
N2 N1 H1 115(3) . . ?
P1 N1 H1 127(3) . . ?
C3 C2 C1 108.5(3) . . ?
C3 C2 Fe1 69.92(16) . . ?
C1 C2 Fe1 69.74(15) . . ?
C3 C2 H2 125.7 . . ?
C1 C2 H2 125.7 . . ?
Fe1 C2 H2 125.7 . . ?
C12 N2 N1 107.7(3) . . ?
C2 C3 C4 108.2(3) . . ?
C2 C3 Fe1 69.50(16) . . ?
C4 C3 Fe1 69.38(17) . . ?
C2 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
Fe1 C3 H3 125.9 . . ?
C4 C5 C1 108.3(3) . . ?
C4 C5 Fe1 69.73(16) . . ?
C1 C5 Fe1 70.09(16) . . ?
C4 C5 H5 125.8 . . ?
C1 C5 H5 125.8 . . ?
Fe1 C5 H5 125.8 . . ?
C3 C4 C5 108.1(3) . . ?
C3 C4 Fe1 69.98(16) . . ?
C5 C4 Fe1 69.26(16) . . ?
C3 C4 H4 126.0 . . ?
C5 C4 H4 126.0 . . ?
Fe1 C4 H4 126.0 . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C11 C6 C7 117.8(3) . . ?
C11 C6 C1 120.5(3) . . ?
C7 C6 C1 121.7(3) . . ?
C8 C9 C10 117.9(3) . . ?
C8 C9 C12 122.0(3) . . ?
C10 C9 C12 120.1(3) . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C6 121.5(3) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
N2 C12 C13 114.9(3) . . ?
N2 C12 C9 118.4(3) . . ?
C13 C12 C9 126.6(3) . . ?
C12 C13 P1 111.0(2) . . ?
C12 C13 H13 124.5 . . ?
P1 C13 H13 124.5 . . ?
C18 C14 C15 108.0(3) . . ?
C18 C14 Fe1 69.67(19) . . ?
C15 C14 Fe1 69.81(19) . . ?
C18 C14 H14 126.0 . . ?
C15 C14 H14 126.0 . . ?
Fe1 C14 H14 126.0 . . ?
C16 C15 C14 107.9(3) . . ?
C16 C15 Fe1 69.97(19) . . ?
C14 C15 Fe1 69.61(19) . . ?
C16 C15 H15 126.1 . . ?
C14 C15 H15 126.1 . . ?
Fe1 C15 H15 126.1 . . ?
C15 C16 C17 108.6(3) . . ?
C15 C16 Fe1 69.82(19) . . ?
C17 C16 Fe1 69.90(19) . . ?
C15 C16 H16 125.7 . . ?
C17 C16 H16 125.7 . . ?
Fe1 C16 H16 125.7 . . ?
C16 C17 C18 107.9(3) . . ?
C16 C17 Fe1 69.89(18) . . ?
C18 C17 Fe1 69.45(18) . . ?
C16 C17 H17 126.1 . . ?
C18 C17 H17 126.1 . . ?
Fe1 C17 H17 126.1 . . ?
C14 C18 C17 107.7(3) . . ?
C14 C18 Fe1 69.77(19) . . ?
C17 C18 Fe1 69.90(18) . . ?
C14 C18 H18 126.1 . . ?
C17 C18 H18 126.1 . . ?
Fe1 C18 H18 126.1 . . ?

_refine_diff_density_max         0.902
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.087


_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_me181210Fe1
_database_code_depnum_ccdc_archive 'CCDC 2053760'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 Fe N2 P'
_chemical_formula_weight         270.05

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'
Fe Fe 0.3463 0.8444 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, -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'

_cell_length_a                   41.9024(10)
_cell_length_b                   10.1534(3)
_cell_length_c                   21.7438(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.1470(10)
_cell_angle_gamma                90
_cell_volume                     8970.4(4)
_cell_formula_units_Z            32
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    110656
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_F_000             4416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.176
_exptl_absorpt_coefficient_mu    1.457
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6671
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.894
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            94553
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_h_max       53
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.333
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             9768
_reflns_number_gt                7977
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0204P)²+17.6401P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13816
_refine_ls_number_parameters     581
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0652
_refine_ls_wR_factor_gt          0.0621
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.69223(2) 1.09542(3) 0.45264(2) 0.01781(7) Uani 1 1 d . . . . .
C1 C 0.66560(5) 1.0990(2) 0.52036(10) 0.0196(4) Uani 1 1 d . . . . .
N1' N 0.65770(4) 0.88559(19) 0.64589(8) 0.0246(4) Uani 1 1 d . . . . .
H1' H 0.644609 0.835632 0.661986 0.029 Uiso 1 1 calc R U . . .
P1 P 0.69758(2) 0.90381(7) 0.68275(3) 0.03014(14) Uani 1 1 d . . . . .
Fe2 Fe 0.68619(2) 0.42284(3) 0.76480(2) 0.02146(7) Uani 1 1 d . . . . .
C2 C 0.68004(5) 1.2251(2) 0.51508(11) 0.0226(5) Uani 1 1 d . . . . .
H2 H 0.695842 1.272840 0.549840 0.027 Uiso 1 1 calc R U . . .
N2' N 0.64643(4) 0.95036(18) 0.59064(8) 0.0217(4) Uani 1 1 d . . . . .
P2 P 0.68469(2) 0.66161(7) 0.53306(3) 0.03124(15) Uani 1 1 d . . . . .
Fe4 Fe 0.56955(2) 1.09935(3) 0.73662(2) 0.02075(7) Uani 1 1 d . . . . .
C4 C 0.64639(5) 1.1731(2) 0.41769(11) 0.0267(5) Uani 1 1 d . . . . .
H4 H 0.634447 1.178136 0.371923 0.032 Uiso 1 1 calc R U . . .
N4' N 0.64675(4) 0.5405(2) 0.59275(9) 0.0265(4) Uani 1 1 d . . . . .
P4 P 0.55137(2) 0.61424(6) 0.63212(3) 0.02564(13) Uani 1 1 d . . . . .
Fe3 Fe 0.55793(2) 0.39972(3) 0.42189(2) 0.01889(7) Uani 1 1 d . . . . .
C3 C 0.66807(5) 1.2703(2) 0.45191(11) 0.0275(5) Uani 1 1 d . . . . .
H3 H 0.673977 1.355446 0.434406 0.033 Uiso 1 1 calc R U . . .
N3' N 0.64788(5) 0.6246(2) 0.54532(9) 0.0303(5) Uani 1 1 d . . . . .
H3' H 0.629760 0.659007 0.521530 0.036 Uiso 1 1 calc R U . . .
P3 P 0.54375(2) 0.89778(6) 0.50608(3) 0.02639(13) Uani 1 1 d . . . . .
N6' N 0.58900(4) 0.75368(18) 0.47699(8) 0.0214(4) Uani 1 1 d . . . . .
C6 C 0.67134(5) 1.0189(2) 0.57794(10) 0.0189(4) Uani 1 1 d . . . . .
N5' N 0.58305(4) 0.85677(18) 0.51210(8) 0.0228(4) Uani 1 1 d . . . . .
H5' H 0.599259 0.900540 0.537142 0.027 Uiso 1 1 calc R U . . .
C5 C 0.64483(5) 1.0673(2) 0.45956(10) 0.0229(5) Uani 1 1 d . . . . .
H5 H 0.631630 0.984805 0.448431 0.027 Uiso 1 1 calc R U . . .
N8' N 0.60352(4) 0.74913(17) 0.68533(8) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.72729(5) 0.9504(2) 0.47484(11) 0.0238(5) Uani 1 1 d . . . . .
H8 H 0.730461 0.888176 0.511490 0.029 Uiso 1 1 calc R U . . .
N7' N 0.59159(4) 0.64804(19) 0.64560(9) 0.0224(4) Uani 1 1 d . . . . .
H7' H 0.6054(6) 0.609(2) 0.6310(11) 0.023(6) Uiso 1 1 d . . . . .
C7 C 0.70141(5) 1.0067(2) 0.62325(10) 0.0251(5) Uani 1 1 d . . . . .
H7 H 0.721200 1.050012 0.621015 0.030 Uiso 1 1 calc R U . . .
C9 C 0.74235(5) 1.0758(2) 0.47529(10) 0.0232(5) Uani 1 1 d . . . . .
H9 H 0.758049 1.117313 0.512331 0.028 Uiso 1 1 calc R U . . .
C10 C 0.73101(5) 1.1325(2) 0.41402(11) 0.0256(5) Uani 1 1 d . . . . .
H10 H 0.737450 1.220552 0.400309 0.031 Uiso 1 1 calc R U . . .
C11 C 0.70897(6) 1.0419(3) 0.37571(11) 0.0301(5) Uani 1 1 d . . . . .
H11 H 0.697135 1.054969 0.330281 0.036 Uiso 1 1 calc R U . . .
C12 C 0.70673(6) 0.9294(2) 0.41322(11) 0.0286(5) Uani 1 1 d . . . . .
H12 H 0.692879 0.849729 0.398910 0.034 Uiso 1 1 calc R U . . .
C101 C 0.68387(5) 0.4027(2) 0.66971(10) 0.0229(5) Uani 1 1 d . . . . .
C102 C 0.71559(6) 0.3646(2) 0.70737(10) 0.0258(5) Uani 1 1 d . . . . .
H102 H 0.737037 0.405856 0.705689 0.031 Uiso 1 1 calc R U . . .
C103 C 0.71152(7) 0.2604(2) 0.74806(12) 0.0362(6) Uani 1 1 d . . . . .
H103 H 0.729501 0.214775 0.779618 0.043 Uiso 1 1 calc R U . . .
C104 C 0.67765(7) 0.2323(2) 0.73617(13) 0.0418(7) Uani 1 1 d . . . . .
H104 H 0.667425 0.163303 0.758034 0.050 Uiso 1 1 calc R U . . .
C105 C 0.66042(6) 0.3190(2) 0.68814(11) 0.0330(6) Uani 1 1 d . . . . .
H105 H 0.636032 0.321543 0.670527 0.040 Uiso 1 1 calc R U . . .
C106 C 0.67764(5) 0.5032(2) 0.62015(10) 0.0198(4) Uani 1 1 d . . . . .
C107 C 0.70188(5) 0.5606(2) 0.59455(10) 0.0243(5) Uani 1 1 d . . . . .
H107 H 0.724835 0.545246 0.609519 0.029 Uiso 1 1 calc R U . . .
C201 C 0.55933(5) 0.5958(2) 0.40023(10) 0.0202(4) Uani 1 1 d . . . . .
C112 C 0.65339(6) 0.5281(3) 0.80089(11) 0.0337(6) Uani 1 1 d . . . . .
H112 H 0.628900 0.526885 0.784927 0.040 Uiso 1 1 calc R U . . .
C111 C 0.67239(7) 0.4438(3) 0.84792(11) 0.0369(6) Uani 1 1 d . . . . .
H111 H 0.663592 0.372470 0.870913 0.044 Uiso 1 1 calc R U . . .
C110 C 0.70595(6) 0.4773(3) 0.85623(11) 0.0342(6) Uani 1 1 d . . . . .
H110 H 0.725004 0.434160 0.886229 0.041 Uiso 1 1 calc R U . . .
C109 C 0.70782(6) 0.5826(2) 0.81467(11) 0.0310(5) Uani 1 1 d . . . . .
H109 H 0.728419 0.626949 0.810068 0.037 Uiso 1 1 calc R U . . .
C108 C 0.67532(6) 0.6144(2) 0.78073(11) 0.0300(5) Uani 1 1 d . . . . .
H108 H 0.669030 0.684603 0.747731 0.036 Uiso 1 1 calc R U . . .
C202 C 0.53011(5) 0.5354(2) 0.36274(10) 0.0250(5) Uani 1 1 d . . . . .
H202 H 0.506986 0.561153 0.362025 0.030 Uiso 1 1 calc R U . . .
C203 C 0.53969(6) 0.4325(2) 0.32702(10) 0.0305(5) Uani 1 1 d . . . . .
H203 H 0.524420 0.372827 0.296915 0.037 Uiso 1 1 calc R U . . .
C204 C 0.57446(6) 0.4270(2) 0.34178(11) 0.0308(5) Uani 1 1 d . . . . .
H204 H 0.587978 0.363269 0.323819 0.037 Uiso 1 1 calc R U . . .
C205 C 0.58682(5) 0.5268(2) 0.38707(10) 0.0251(5) Uani 1 1 d . . . . .
H205 H 0.610571 0.545779 0.406427 0.030 Uiso 1 1 calc R U . . .
C206 C 0.56007(5) 0.7066(2) 0.44373(9) 0.0180(4) Uani 1 1 d . . . . .
C207 C 0.53237(5) 0.7729(2) 0.45329(10) 0.0219(5) Uani 1 1 d . . . . .
H207 H 0.510259 0.751040 0.433031 0.026 Uiso 1 1 calc R U . . .
C208 C 0.58833(6) 0.2976(2) 0.49438(10) 0.0263(5) Uani 1 1 d . . . . .
H208 H 0.612940 0.298936 0.505246 0.032 Uiso 1 1 calc R U . . .
C209 C 0.56796(6) 0.3845(2) 0.51828(11) 0.0309(5) Uani 1 1 d . . . . .
H209 H 0.575658 0.457509 0.549192 0.037 Uiso 1 1 calc R U . . .
C210 C 0.53484(6) 0.3505(2) 0.49100(12) 0.0342(6) Uani 1 1 d . . . . .
H210 H 0.515001 0.394766 0.499353 0.041 Uiso 1 1 calc R U . . .
C211 C 0.53475(6) 0.2421(2) 0.45000(12) 0.0323(6) Uani 1 1 d . . . . .
H211 H 0.514789 0.196626 0.424083 0.039 Uiso 1 1 calc R U . . .
C212 C 0.56794(6) 0.2093(2) 0.45200(11) 0.0280(5) Uani 1 1 d . . . . .
H212 H 0.575517 0.136908 0.427761 0.034 Uiso 1 1 calc R U . . .
C301 C 0.58509(5) 0.9086(2) 0.75186(10) 0.0229(5) Uani 1 1 d . . . . .
C302 C 0.56499(6) 0.9449(2) 0.79349(10) 0.0280(5) Uani 1 1 d . . . . .
H302 H 0.543890 0.901593 0.795860 0.034 Uiso 1 1 calc R U . . .
C303 C 0.57995(7) 1.0535(2) 0.83063(10) 0.0347(6) Uani 1 1 d . . . . .
H303 H 0.571240 1.099895 0.863680 0.042 Uiso 1 1 calc R U . . .
C304 C 0.60915(6) 1.0852(3) 0.81247(12) 0.0392(6) Uani 1 1 d . . . . .
H304 H 0.624657 1.158182 0.830370 0.047 Uiso 1 1 calc R U . . .
C305 C 0.61256(6) 0.9963(2) 0.76383(12) 0.0321(6) Uani 1 1 d . . . . .
H305 H 0.630845 0.995889 0.741670 0.039 Uiso 1 1 calc R U . . .
C306 C 0.57866(5) 0.8005(2) 0.70598(9) 0.0186(4) Uani 1 1 d . . . . .
C307 C 0.54808(5) 0.7397(2) 0.68196(10) 0.0222(5) Uani 1 1 d . . . . .
H307 H 0.528183 0.765277 0.692183 0.027 Uiso 1 1 calc R U . . .
C308 C 0.54116(7) 1.1137(3) 0.64672(11) 0.0379(6) Uani 1 1 d . . . . .
H308 H 0.534336 1.038653 0.616568 0.045 Uiso 1 1 calc R U . . .
C309 C 0.52358(6) 1.1608(3) 0.69041(11) 0.0361(6) Uani 1 1 d . . . . .
H309 H 0.502268 1.125448 0.696382 0.043 Uiso 1 1 calc R U . . .
C310 C 0.54181(7) 1.2671(3) 0.72412(12) 0.0378(6) Uani 1 1 d . . . . .
H310 H 0.535697 1.319908 0.758357 0.045 Uiso 1 1 calc R U . . .
C311 C 0.57033(8) 1.2846(3) 0.70108(14) 0.0454(7) Uani 1 1 d . . . . .
H311 H 0.587886 1.351988 0.716246 0.054 Uiso 1 1 calc R U . . .
C312 C 0.56980(8) 1.1898(3) 0.65301(12) 0.0436(7) Uani 1 1 d . . . . .
H312 H 0.586823 1.178679 0.628212 0.052 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C10 2.038(2) . ?
Fe1 C11 2.039(2) . ?
Fe1 C3 2.042(2) . ?
Fe1 C4 2.044(2) . ?
Fe1 C2 2.044(2) . ?
Fe1 C9 2.046(2) . ?
Fe1 C5 2.048(2) . ?
Fe1 C12 2.049(2) . ?
Fe1 C8 2.053(2) . ?
Fe1 C1 2.054(2) . ?
C1 C5 1.431(3) . ?
C1 C2 1.432(3) . ?
C1 C6 1.463(3) . ?
N1' N2' 1.350(2) . ?
N1' P1 1.6776(18) . ?
N1' H1' 0.8800 . ?
P1 C7 1.701(2) . ?
Fe2 C110 2.034(2) . ?
Fe2 C109 2.037(2) . ?
Fe2 C104 2.037(2) . ?
Fe2 C111 2.039(2) . ?
Fe2 C103 2.042(2) . ?
Fe2 C112 2.043(2) . ?
Fe2 C105 2.044(2) . ?
Fe2 C102 2.044(2) . ?
Fe2 C108 2.046(2) . ?
Fe2 C101 2.056(2) . ?
C2 C3 1.418(3) . ?
C2 H2 1.0000 . ?
N2' C6 1.338(3) . ?
P2 N3' 1.671(2) . ?
P2 C107 1.699(2) . ?
Fe4 C308 2.030(2) . ?
Fe4 C302 2.035(2) . ?
Fe4 C311 2.037(3) . ?
Fe4 C303 2.037(2) . ?
Fe4 C312 2.039(2) . ?
Fe4 C304 2.039(2) . ?
Fe4 C309 2.041(2) . ?
Fe4 C305 2.043(2) . ?
Fe4 C310 2.043(2) . ?
Fe4 C301 2.044(2) . ?
C4 C5 1.420(3) . ?
C4 C3 1.422(3) . ?
C4 H4 1.0000 . ?
N4' C106 1.340(3) . ?
N4' N3' 1.349(3) . ?
P4 N7' 1.6741(19) . ?
P4 C307 1.700(2) . ?
Fe3 C205 2.037(2) . ?
Fe3 C210 2.038(2) . ?
Fe3 C209 2.040(2) . ?
Fe3 C211 2.042(2) . ?
Fe3 C203 2.044(2) . ?
Fe3 C202 2.044(2) . ?
Fe3 C204 2.044(2) . ?
Fe3 C208 2.049(2) . ?
Fe3 C201 2.050(2) . ?
Fe3 C212 2.052(2) . ?
C3 H3 1.0000 . ?
N3' H3' 0.8800 . ?
P3 N5' 1.6724(18) . ?
P3 C207 1.698(2) . ?
N6' C206 1.339(3) . ?
N6' N5' 1.354(2) . ?
C6 C7 1.403(3) . ?
N5' H5' 0.8800 . ?
C5 H5 1.0000 . ?
N8' C306 1.337(3) . ?
N8' N7' 1.356(2) . ?
C8 C9 1.420(3) . ?
C8 C12 1.421(3) . ?
C8 H8 1.0000 . ?
N7' H7' 0.82(2) . ?
C7 H7 0.9500 . ?
C9 C10 1.422(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.420(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.420(3) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C101 C105 1.429(3) . ?
C101 C102 1.434(3) . ?
C101 C106 1.460(3) . ?
C102 C103 1.416(3) . ?
C102 H102 1.0000 . ?
C103 C104 1.408(4) . ?
C103 H103 1.0000 . ?
C104 C105 1.421(4) . ?
C104 H104 1.0000 . ?
C105 H105 1.0000 . ?
C106 C107 1.399(3) . ?
C107 H107 0.9500 . ?
C201 C202 1.432(3) . ?
C201 C205 1.436(3) . ?
C201 C206 1.465(3) . ?
C112 C108 1.414(4) . ?
C112 C111 1.420(4) . ?
C112 H112 1.0000 . ?
C111 C110 1.415(4) . ?
C111 H111 1.0000 . ?
C110 C109 1.414(3) . ?
C110 H110 1.0000 . ?
C109 C108 1.418(3) . ?
C109 H109 1.0000 . ?
C108 H108 1.0000 . ?
C202 C203 1.418(3) . ?
C202 H202 1.0000 . ?
C203 C204 1.414(3) . ?
C203 H203 1.0000 . ?
C204 C205 1.420(3) . ?
C204 H204 1.0000 . ?
C205 H205 1.0000 . ?
C206 C207 1.400(3) . ?
C207 H207 0.9500 . ?
C208 C209 1.412(3) . ?
C208 C212 1.414(3) . ?
C208 H208 1.0000 . ?
C209 C210 1.412(3) . ?
C209 H209 1.0000 . ?
C210 C211 1.416(4) . ?
C210 H210 1.0000 . ?
C211 C212 1.421(3) . ?
C211 H211 1.0000 . ?
C212 H212 1.0000 . ?
C301 C305 1.427(3) . ?
C301 C302 1.427(3) . ?
C301 C306 1.464(3) . ?
C302 C303 1.419(3) . ?
C302 H302 1.0000 . ?
C303 C304 1.411(4) . ?
C303 H303 1.0000 . ?
C304 C305 1.424(3) . ?
C304 H304 1.0000 . ?
C305 H305 1.0000 . ?
C306 C307 1.403(3) . ?
C307 H307 0.9500 . ?
C308 C312 1.406(4) . ?
C308 C309 1.420(3) . ?
C308 H308 1.0000 . ?
C309 C310 1.419(4) . ?
C309 H309 1.0000 . ?
C310 C311 1.415(4) . ?
C310 H310 1.0000 . ?
C311 C312 1.417(4) . ?
C311 H311 1.0000 . ?
C312 H312 1.0000 . ?

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
C10 Fe1 C11 40.77(9) . . ?
C10 Fe1 C3 106.25(9) . . ?
C11 Fe1 C3 119.65(10) . . ?
C10 Fe1 C4 123.16(9) . . ?
C11 Fe1 C4 106.17(9) . . ?
C3 Fe1 C4 40.73(9) . . ?
C10 Fe1 C2 120.57(9) . . ?
C11 Fe1 C2 155.30(10) . . ?
C3 Fe1 C2 40.62(9) . . ?
C4 Fe1 C2 68.49(9) . . ?
C10 Fe1 C9 40.76(9) . . ?
C11 Fe1 C9 68.47(9) . . ?
C3 Fe1 C9 124.35(9) . . ?
C4 Fe1 C9 160.60(9) . . ?
C2 Fe1 C9 108.14(9) . . ?
C10 Fe1 C5 160.23(9) . . ?
C11 Fe1 C5 123.86(9) . . ?
C3 Fe1 C5 68.54(9) . . ?
C4 Fe1 C5 40.62(9) . . ?
C2 Fe1 C5 68.70(9) . . ?
C9 Fe1 C5 157.72(9) . . ?
C10 Fe1 C12 68.41(9) . . ?
C11 Fe1 C12 40.64(10) . . ?
C3 Fe1 C12 155.38(9) . . ?
C4 Fe1 C12 120.65(9) . . ?
C2 Fe1 C12 162.85(9) . . ?
C9 Fe1 C12 68.21(9) . . ?
C5 Fe1 C12 107.93(9) . . ?
C10 Fe1 C8 68.45(9) . . ?
C11 Fe1 C8 68.39(9) . . ?
C3 Fe1 C8 161.92(9) . . ?
C4 Fe1 C8 156.65(9) . . ?
C2 Fe1 C8 125.93(9) . . ?
C9 Fe1 C8 40.54(9) . . ?
C5 Fe1 C8 122.26(9) . . ?
C12 Fe1 C8 40.53(9) . . ?
C10 Fe1 C1 156.88(9) . . ?
C11 Fe1 C1 161.60(10) . . ?
C3 Fe1 C1 68.58(9) . . ?
C4 Fe1 C1 68.50(9) . . ?
C2 Fe1 C1 40.92(8) . . ?
C9 Fe1 C1 122.33(8) . . ?
C5 Fe1 C1 40.82(8) . . ?
C12 Fe1 C1 125.67(9) . . ?
C8 Fe1 C1 109.11(9) . . ?
C5 C1 C2 107.52(19) . . ?
C5 C1 C6 126.95(19) . . ?
C2 C1 C6 125.53(19) . . ?
C5 C1 Fe1 69.39(11) . . ?
C2 C1 Fe1 69.17(12) . . ?
C6 C1 Fe1 126.81(15) . . ?
N2' N1' P1 117.55(14) . . ?
N2' N1' H1' 121.2 . . ?
P1 N1' H1' 121.2 . . ?
N1' P1 C7 88.43(10) . . ?
C110 Fe2 C109 40.66(10) . . ?
C110 Fe2 C104 123.77(11) . . ?
C109 Fe2 C104 160.26(11) . . ?
C110 Fe2 C111 40.66(10) . . ?
C109 Fe2 C111 68.33(10) . . ?
C104 Fe2 C111 107.65(11) . . ?
C110 Fe2 C103 106.77(10) . . ?
C109 Fe2 C103 123.73(11) . . ?
C104 Fe2 C103 40.40(11) . . ?
C111 Fe2 C103 120.97(10) . . ?
C110 Fe2 C112 68.52(10) . . ?
C109 Fe2 C112 68.43(10) . . ?
C104 Fe2 C112 122.00(11) . . ?
C111 Fe2 C112 40.70(10) . . ?
C103 Fe2 C112 156.78(11) . . ?
C110 Fe2 C105 160.91(11) . . ?
C109 Fe2 C105 157.34(10) . . ?
C104 Fe2 C105 40.74(11) . . ?
C111 Fe2 C105 124.69(10) . . ?
C103 Fe2 C105 68.40(11) . . ?
C112 Fe2 C105 108.20(10) . . ?
C110 Fe2 C102 120.88(10) . . ?
C109 Fe2 C102 107.41(10) . . ?
C104 Fe2 C102 68.02(10) . . ?
C111 Fe2 C102 156.27(10) . . ?
C103 Fe2 C102 40.56(9) . . ?
C112 Fe2 C102 161.50(10) . . ?
C105 Fe2 C102 68.27(9) . . ?
C110 Fe2 C108 68.32(10) . . ?
C109 Fe2 C108 40.65(9) . . ?
C104 Fe2 C108 157.62(11) . . ?
C111 Fe2 C108 68.15(10) . . ?
C103 Fe2 C108 160.90(11) . . ?
C112 Fe2 C108 40.47(10) . . ?
C105 Fe2 C108 122.23(10) . . ?
C102 Fe2 C108 124.79(10) . . ?
C110 Fe2 C101 156.56(10) . . ?
C109 Fe2 C101 121.33(10) . . ?
C104 Fe2 C101 68.69(10) . . ?
C111 Fe2 C101 161.41(10) . . ?
C103 Fe2 C101 68.86(9) . . ?
C112 Fe2 C101 124.57(9) . . ?
C105 Fe2 C101 40.79(9) . . ?
C102 Fe2 C101 40.92(8) . . ?
C108 Fe2 C101 107.88(9) . . ?
C3 C2 C1 108.07(19) . . ?
C3 C2 Fe1 69.61(13) . . ?
C1 C2 Fe1 69.91(12) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
Fe1 C2 H2 126.0 . . ?
C6 N2' N1' 108.43(17) . . ?
N3' P2 C107 88.22(10) . . ?
C308 Fe4 C302 121.37(11) . . ?
C308 Fe4 C311 68.18(12) . . ?
C302 Fe4 C311 162.74(11) . . ?
C308 Fe4 C303 156.07(12) . . ?
C302 Fe4 C303 40.78(10) . . ?
C311 Fe4 C303 124.93(11) . . ?
C308 Fe4 C312 40.42(11) . . ?
C302 Fe4 C312 155.59(11) . . ?
C311 Fe4 C312 40.69(11) . . ?
C303 Fe4 C312 162.01(12) . . ?
C308 Fe4 C304 162.47(12) . . ?
C302 Fe4 C304 68.44(11) . . ?
C311 Fe4 C304 106.67(12) . . ?
C303 Fe4 C304 40.52(11) . . ?
C312 Fe4 C304 124.92(12) . . ?
C308 Fe4 C309 40.84(10) . . ?
C302 Fe4 C309 108.52(11) . . ?
C311 Fe4 C309 68.37(12) . . ?
C303 Fe4 C309 120.59(11) . . ?
C312 Fe4 C309 68.48(11) . . ?
C304 Fe4 C309 154.65(10) . . ?
C308 Fe4 C305 125.69(10) . . ?
C302 Fe4 C305 68.67(10) . . ?
C311 Fe4 C305 119.22(12) . . ?
C303 Fe4 C305 68.59(11) . . ?
C312 Fe4 C305 107.00(11) . . ?
C304 Fe4 C305 40.83(10) . . ?
C309 Fe4 C305 163.59(10) . . ?
C308 Fe4 C310 68.39(10) . . ?
C302 Fe4 C310 126.08(10) . . ?
C311 Fe4 C310 40.60(11) . . ?
C303 Fe4 C310 107.43(10) . . ?
C312 Fe4 C310 68.44(11) . . ?
C304 Fe4 C310 119.39(10) . . ?
C309 Fe4 C310 40.66(10) . . ?
C305 Fe4 C310 154.01(11) . . ?
C308 Fe4 C301 108.20(10) . . ?
C302 Fe4 C301 40.97(9) . . ?
C311 Fe4 C301 154.45(11) . . ?
C303 Fe4 C301 68.85(9) . . ?
C312 Fe4 C301 120.01(10) . . ?
C304 Fe4 C301 68.76(9) . . ?
C309 Fe4 C301 126.50(10) . . ?
C305 Fe4 C301 40.89(9) . . ?
C310 Fe4 C301 163.76(11) . . ?
C5 C4 C3 108.25(19) . . ?
C5 C4 Fe1 69.87(12) . . ?
C3 C4 Fe1 69.57(12) . . ?
C5 C4 H4 125.9 . . ?
C3 C4 H4 125.9 . . ?
Fe1 C4 H4 125.9 . . ?
C106 N4' N3' 107.96(18) . . ?
N7' P4 C307 88.27(10) . . ?
C205 Fe3 C210 149.47(10) . . ?
C205 Fe3 C209 115.97(10) . . ?
C210 Fe3 C209 40.51(10) . . ?
C205 Fe3 C211 167.68(10) . . ?
C210 Fe3 C211 40.61(10) . . ?
C209 Fe3 C211 68.07(10) . . ?
C205 Fe3 C203 68.39(9) . . ?
C210 Fe3 C203 131.00(10) . . ?
C209 Fe3 C203 168.88(10) . . ?
C211 Fe3 C203 109.98(10) . . ?
C205 Fe3 C202 68.82(9) . . ?
C210 Fe3 C202 109.18(9) . . ?
C209 Fe3 C202 129.79(10) . . ?
C211 Fe3 C202 118.48(9) . . ?
C203 Fe3 C202 40.57(9) . . ?
C205 Fe3 C204 40.71(9) . . ?
C210 Fe3 C204 169.11(10) . . ?
C209 Fe3 C204 149.08(10) . . ?
C211 Fe3 C204 130.26(10) . . ?
C203 Fe3 C204 40.47(10) . . ?
C202 Fe3 C204 68.44(10) . . ?
C205 Fe3 C208 106.98(9) . . ?
C210 Fe3 C208 68.09(9) . . ?
C209 Fe3 C208 40.38(9) . . ?
C211 Fe3 C208 67.98(9) . . ?
C203 Fe3 C208 150.13(10) . . ?
C202 Fe3 C208 167.55(9) . . ?
C204 Fe3 C208 116.58(10) . . ?
C205 Fe3 C201 41.13(9) . . ?
C210 Fe3 C201 116.92(9) . . ?
C209 Fe3 C201 107.42(9) . . ?
C211 Fe3 C201 150.74(9) . . ?
C203 Fe3 C201 68.59(9) . . ?
C202 Fe3 C201 40.95(8) . . ?
C204 Fe3 C201 68.79(9) . . ?
C208 Fe3 C201 128.36(9) . . ?
C205 Fe3 C212 128.44(9) . . ?
C210 Fe3 C212 68.32(10) . . ?
C209 Fe3 C212 68.03(10) . . ?
C211 Fe3 C212 40.61(9) . . ?
C203 Fe3 C212 118.18(10) . . ?
C202 Fe3 C212 151.25(9) . . ?
C204 Fe3 C212 108.31(10) . . ?
C208 Fe3 C212 40.34(9) . . ?
C201 Fe3 C212 166.79(9) . . ?
C2 C3 C4 108.2(2) . . ?
C2 C3 Fe1 69.77(12) . . ?
C4 C3 Fe1 69.70(13) . . ?
C2 C3 H3 125.9 . . ?
C4 C3 H3 125.9 . . ?
Fe1 C3 H3 125.9 . . ?
N4' N3' P2 118.08(14) . . ?
N4' N3' H3' 121.0 . . ?
P2 N3' H3' 121.0 . . ?
N5' P3 C207 88.59(10) . . ?
C206 N6' N5' 108.27(17) . . ?
N2' C6 C7 114.92(19) . . ?
N2' C6 C1 119.50(18) . . ?
C7 C6 C1 125.57(19) . . ?
N6' N5' P3 117.49(14) . . ?
N6' N5' H5' 121.3 . . ?
P3 N5' H5' 121.3 . . ?
C4 C5 C1 107.98(19) . . ?
C4 C5 Fe1 69.50(12) . . ?
C1 C5 Fe1 69.79(11) . . ?
C4 C5 H5 126.0 . . ?
C1 C5 H5 126.0 . . ?
Fe1 C5 H5 126.0 . . ?
C306 N8' N7' 108.23(17) . . ?
C9 C8 C12 107.9(2) . . ?
C9 C8 Fe1 69.49(12) . . ?
C12 C8 Fe1 69.61(13) . . ?
C9 C8 H8 126.1 . . ?
C12 C8 H8 126.1 . . ?
Fe1 C8 H8 126.1 . . ?
N8' N7' P4 117.73(14) . . ?
N8' N7' H7' 115.0(16) . . ?
P4 N7' H7' 127.2(16) . . ?
C6 C7 P1 110.65(16) . . ?
C6 C7 H7 124.7 . . ?
P1 C7 H7 124.7 . . ?
C8 C9 C10 108.08(19) . . ?
C8 C9 Fe1 69.97(12) . . ?
C10 C9 Fe1 69.32(12) . . ?
C8 C9 H9 126.0 . . ?
C10 C9 H9 126.0 . . ?
Fe1 C9 H9 126.0 . . ?
C11 C10 C9 107.9(2) . . ?
C11 C10 Fe1 69.66(13) . . ?
C9 C10 Fe1 69.93(12) . . ?
C11 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
Fe1 C10 H10 126.0 . . ?
C12 C11 C10 108.0(2) . . ?
C12 C11 Fe1 70.05(13) . . ?
C10 C11 Fe1 69.57(12) . . ?
C12 C11 H11 126.0 . . ?
C10 C11 H11 126.0 . . ?
Fe1 C11 H11 126.0 . . ?
C11 C12 C8 108.1(2) . . ?
C11 C12 Fe1 69.31(13) . . ?
C8 C12 Fe1 69.86(13) . . ?
C11 C12 H12 125.9 . . ?
C8 C12 H12 125.9 . . ?
Fe1 C12 H12 125.9 . . ?
C105 C101 C102 106.5(2) . . ?
C105 C101 C106 127.7(2) . . ?
C102 C101 C106 125.7(2) . . ?
C105 C101 Fe2 69.13(13) . . ?
C102 C101 Fe2 69.10(12) . . ?
C106 C101 Fe2 128.94(15) . . ?
C103 C102 C101 108.8(2) . . ?
C103 C102 Fe2 69.63(13) . . ?
C101 C102 Fe2 69.98(12) . . ?
C103 C102 H102 125.6 . . ?
C101 C102 H102 125.6 . . ?
Fe2 C102 H102 125.6 . . ?
C104 C103 C102 107.8(2) . . ?
C104 C103 Fe2 69.60(14) . . ?
C102 C103 Fe2 69.81(13) . . ?
C104 C103 H103 126.1 . . ?
C102 C103 H103 126.1 . . ?
Fe2 C103 H103 126.1 . . ?
C103 C104 C105 108.5(2) . . ?
C103 C104 Fe2 70.00(14) . . ?
C105 C104 Fe2 69.89(14) . . ?
C103 C104 H104 125.7 . . ?
C105 C104 H104 125.7 . . ?
Fe2 C104 H104 125.7 . . ?
C104 C105 C101 108.3(2) . . ?
C104 C105 Fe2 69.37(14) . . ?
C101 C105 Fe2 70.08(12) . . ?
C104 C105 H105 125.9 . . ?
C101 C105 H105 125.9 . . ?
Fe2 C105 H105 125.9 . . ?
N4' C106 C107 114.9(2) . . ?
N4' C106 C101 120.3(2) . . ?
C107 C106 C101 124.66(19) . . ?
C106 C107 P2 110.82(16) . . ?
C106 C107 H107 124.6 . . ?
P2 C107 H107 124.6 . . ?
C202 C201 C205 107.05(19) . . ?
C202 C201 C206 125.2(2) . . ?
C205 C201 C206 127.74(19) . . ?
C202 C201 Fe3 69.30(12) . . ?
C205 C201 Fe3 68.95(12) . . ?
C206 C201 Fe3 126.49(14) . . ?
C108 C112 C111 107.7(2) . . ?
C108 C112 Fe2 69.89(13) . . ?
C111 C112 Fe2 69.49(13) . . ?
C108 C112 H112 126.1 . . ?
C111 C112 H112 126.1 . . ?
Fe2 C112 H112 126.1 . . ?
C110 C111 C112 108.2(2) . . ?
C110 C111 Fe2 69.50(14) . . ?
C112 C111 Fe2 69.81(13) . . ?
C110 C111 H111 125.9 . . ?
C112 C111 H111 125.9 . . ?
Fe2 C111 H111 125.9 . . ?
C111 C110 C109 108.0(2) . . ?
C111 C110 Fe2 69.84(14) . . ?
C109 C110 Fe2 69.76(13) . . ?
C111 C110 H110 126.0 . . ?
C109 C110 H110 126.0 . . ?
Fe2 C110 H110 126.0 . . ?
C110 C109 C108 108.0(2) . . ?
C110 C109 Fe2 69.58(14) . . ?
C108 C109 Fe2 70.03(13) . . ?
C110 C109 H109 126.0 . . ?
C108 C109 H109 126.0 . . ?
Fe2 C109 H109 126.0 . . ?
C112 C108 C109 108.2(2) . . ?
C112 C108 Fe2 69.64(14) . . ?
C109 C108 Fe2 69.32(13) . . ?
C112 C108 H108 125.9 . . ?
C109 C108 H108 125.9 . . ?
Fe2 C108 H108 125.9 . . ?
C203 C202 C201 108.1(2) . . ?
C203 C202 Fe3 69.71(13) . . ?
C201 C202 Fe3 69.75(12) . . ?
C203 C202 H202 126.0 . . ?
C201 C202 H202 126.0 . . ?
Fe3 C202 H202 126.0 . . ?
C204 C203 C202 108.6(2) . . ?
C204 C203 Fe3 69.77(13) . . ?
C202 C203 Fe3 69.71(12) . . ?
C204 C203 H203 125.7 . . ?
C202 C203 H203 125.7 . . ?
Fe3 C203 H203 125.7 . . ?
C203 C204 C205 108.1(2) . . ?
C203 C204 Fe3 69.76(13) . . ?
C205 C204 Fe3 69.37(12) . . ?
C203 C204 H204 126.0 . . ?
C205 C204 H204 126.0 . . ?
Fe3 C204 H204 126.0 . . ?
C204 C205 C201 108.2(2) . . ?
C204 C205 Fe3 69.92(13) . . ?
C201 C205 Fe3 69.92(12) . . ?
C204 C205 H205 125.9 . . ?
C201 C205 H205 125.9 . . ?
Fe3 C205 H205 125.9 . . ?
N6' C206 C207 114.97(19) . . ?
N6' C206 C201 119.76(18) . . ?
C207 C206 C201 125.25(18) . . ?
C206 C207 P3 110.67(15) . . ?
C206 C207 H207 124.7 . . ?
P3 C207 H207 124.7 . . ?
C209 C208 C212 108.2(2) . . ?
C209 C208 Fe3 69.46(13) . . ?
C212 C208 Fe3 69.92(13) . . ?
C209 C208 H208 125.9 . . ?
C212 C208 H208 125.9 . . ?
Fe3 C208 H208 125.9 . . ?
C210 C209 C208 108.3(2) . . ?
C210 C209 Fe3 69.67(13) . . ?
C208 C209 Fe3 70.16(13) . . ?
C210 C209 H209 125.9 . . ?
C208 C209 H209 125.9 . . ?
Fe3 C209 H209 125.9 . . ?
C209 C210 C211 107.8(2) . . ?
C209 C210 Fe3 69.82(13) . . ?
C211 C210 Fe3 69.82(13) . . ?
C209 C210 H210 126.1 . . ?
C211 C210 H210 126.1 . . ?
Fe3 C210 H210 126.1 . . ?
C210 C211 C212 108.1(2) . . ?
C210 C211 Fe3 69.57(13) . . ?
C212 C211 Fe3 70.08(13) . . ?
C210 C211 H211 125.9 . . ?
C212 C211 H211 125.9 . . ?
Fe3 C211 H211 125.9 . . ?
C208 C212 C211 107.6(2) . . ?
C208 C212 Fe3 69.74(13) . . ?
C211 C212 Fe3 69.31(13) . . ?
C208 C212 H212 126.2 . . ?
C211 C212 H212 126.2 . . ?
Fe3 C212 H212 126.2 . . ?
C305 C301 C302 107.3(2) . . ?
C305 C301 C306 126.7(2) . . ?
C302 C301 C306 125.9(2) . . ?
C305 C301 Fe4 69.49(13) . . ?
C302 C301 Fe4 69.16(12) . . ?
C306 C301 Fe4 127.01(14) . . ?
C303 C302 C301 108.3(2) . . ?
C303 C302 Fe4 69.69(13) . . ?
C301 C302 Fe4 69.87(13) . . ?
C303 C302 H302 125.8 . . ?
C301 C302 H302 125.8 . . ?
Fe4 C302 H302 125.8 . . ?
C304 C303 C302 108.1(2) . . ?
C304 C303 Fe4 69.81(14) . . ?
C302 C303 Fe4 69.52(12) . . ?
C304 C303 H303 126.0 . . ?
C302 C303 H303 126.0 . . ?
Fe4 C303 H303 126.0 . . ?
C303 C304 C305 108.3(2) . . ?
C303 C304 Fe4 69.67(13) . . ?
C305 C304 Fe4 69.73(13) . . ?
C303 C304 H304 125.8 . . ?
C305 C304 H304 125.8 . . ?
Fe4 C304 H304 125.8 . . ?
C304 C305 C301 107.9(2) . . ?
C304 C305 Fe4 69.44(13) . . ?
C301 C305 Fe4 69.62(12) . . ?
C304 C305 H305 126.0 . . ?
C301 C305 H305 126.0 . . ?
Fe4 C305 H305 126.0 . . ?
N8' C306 C307 114.79(19) . . ?
N8' C306 C301 119.50(19) . . ?
C307 C306 C301 125.67(19) . . ?
C306 C307 P4 110.98(16) . . ?
C306 C307 H307 124.5 . . ?
P4 C307 H307 124.5 . . ?
C312 C308 C309 108.6(2) . . ?
C312 C308 Fe4 70.15(15) . . ?
C309 C308 Fe4 69.98(13) . . ?
C312 C308 H308 125.7 . . ?
C309 C308 H308 125.7 . . ?
Fe4 C308 H308 125.7 . . ?
C310 C309 C308 107.5(2) . . ?
C310 C309 Fe4 69.75(13) . . ?
C308 C309 Fe4 69.18(14) . . ?
C310 C309 H309 126.3 . . ?
C308 C309 H309 126.3 . . ?
Fe4 C309 H309 126.3 . . ?
C311 C310 C309 107.9(2) . . ?
C311 C310 Fe4 69.47(14) . . ?
C309 C310 Fe4 69.59(14) . . ?
C311 C310 H310 126.1 . . ?
C309 C310 H310 126.1 . . ?
Fe4 C310 H310 126.1 . . ?
C310 C311 C312 108.3(3) . . ?
C310 C311 Fe4 69.93(15) . . ?
C312 C311 Fe4 69.75(15) . . ?
C310 C311 H311 125.8 . . ?
C312 C311 H311 125.8 . . ?
Fe4 C311 H311 125.8 . . ?
C308 C312 C311 107.7(2) . . ?
C308 C312 Fe4 69.43(14) . . ?
C311 C312 Fe4 69.56(15) . . ?
C308 C312 H312 126.1 . . ?
C311 C312 H312 126.1 . . ?
Fe4 C312 H312 126.1 . . ?

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
N1' H1' N8' 0.88 2.10 2.960(3) 164.5 . yes
N3' H3' N6' 0.88 1.99 2.867(3) 172.4 . yes
N5' H5' N2' 0.88 2.10 2.942(2) 161.1 . yes
N7' H7' N4' 0.82(2) 2.21(2) 3.026(3) 170(2) . yes

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_me180521Fe1
_database_code_depnum_ccdc_archive 'CCDC 2053765'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice, Faculty of Chemical Technology, Pardubice
Czech Republic
;
_audit_update_record             
;
2021-01-04 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 Fe N2 O P'
_chemical_formula_weight         312.08

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'
Fe Fe 0.3463 0.8444 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   11.6640(8)
_cell_length_b                   7.3497(5)
_cell_length_c                   15.3627(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.718(2)
_cell_angle_gamma                90
_cell_volume                     1316.40(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    27273
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.590
_exptl_crystal_size_mid          0.509
_exptl_crystal_size_min          0.376
_exptl_absorpt_coefficient_mu    1.258
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4410
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.591
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            27273
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.225
_diffrn_reflns_theta_max         27.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3028
_reflns_number_gt                2763
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+0.5209P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0357(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3028
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0746
_refine_ls_goodness_of_fit_ref   1.187
_refine_ls_restrained_S_all      1.187
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 0.76457(2) 0.45668(3) 0.54475(2) 0.01533(10) Uani 1 1 d . . . . .
P1 P 0.46938(4) 0.58168(7) 0.80045(3) 0.02754(14) Uani 1 1 d . . . . .
O1 O 0.30127(12) 0.8844(2) 0.78191(10) 0.0365(3) Uani 1 1 d . . . . .
N1 N 0.46578(12) 0.7670(2) 0.73277(9) 0.0196(3) Uani 1 1 d . . . . .
C1 C 0.72940(13) 0.6417(2) 0.63861(10) 0.0170(3) Uani 1 1 d . . . . .
N2 N 0.55416(11) 0.78559(19) 0.67685(9) 0.0177(3) Uani 1 1 d . . . . .
H2 H 0.6891(19) 0.806(3) 0.5260(14) 0.032(6) Uiso 1 1 d . . . . .
C2 C 0.74688(15) 0.7318(2) 0.55768(11) 0.0194(3) Uani 1 1 d . . . . .
C3 C 0.85922(16) 0.6896(2) 0.53089(12) 0.0245(4) Uani 1 1 d . . . . .
H3 H 0.8941(19) 0.731(3) 0.4781(14) 0.034(6) Uiso 1 1 d . . . . .
C4 C 0.91172(15) 0.5741(3) 0.59473(13) 0.0248(4) Uani 1 1 d . . . . .
H4 H 0.987(2) 0.522(3) 0.5931(16) 0.034(6) Uiso 1 1 d . . . . .
C5 C 0.83206(15) 0.5439(2) 0.66148(12) 0.0210(3) Uani 1 1 d . . . . .
H5 H 0.847(2) 0.477(3) 0.7103(17) 0.033(6) Uiso 1 1 d . . . . .
C6 C 0.62530(14) 0.6481(2) 0.68982(10) 0.0173(3) Uani 1 1 d . . . . .
C8 C 0.37840(15) 0.9006(2) 0.73171(12) 0.0251(4) Uani 1 1 d . . . . .
C7 C 0.59415(17) 0.5213(2) 0.75471(12) 0.0247(4) Uani 1 1 d . . . . .
H7 H 0.6376 0.4163 0.7704 0.030 Uiso 1 1 calc R U . . .
C9 C 0.38952(18) 1.0527(3) 0.66815(15) 0.0323(4) Uani 1 1 d . . . . .
H9A H 0.4006 1.0027 0.6099 0.048 Uiso 1 1 calc R U . . .
H9B H 0.4556 1.1284 0.6852 0.048 Uiso 1 1 calc R U . . .
H9C H 0.3197 1.1268 0.6676 0.048 Uiso 1 1 calc R U . . .
C10 C 0.61778(16) 0.3119(3) 0.52016(14) 0.0303(4) Uani 1 1 d . . . . .
H10 H 0.546(2) 0.333(4) 0.5420(16) 0.044(7) Uiso 1 1 d . . . . .
C11 C 0.66126(17) 0.3806(3) 0.44170(13) 0.0283(4) Uani 1 1 d . . . . .
H11 H 0.626(2) 0.462(4) 0.4032(18) 0.044(7) Uiso 1 1 d . . . . .
C12 C 0.77287(16) 0.3081(2) 0.43208(12) 0.0259(4) Uani 1 1 d . . . . .
H12 H 0.8233(19) 0.335(3) 0.3850(15) 0.036(6) Uiso 1 1 d . . . . .
C13 C 0.79886(17) 0.1964(2) 0.50507(13) 0.0275(4) Uani 1 1 d . . . . .
H13 H 0.8654(19) 0.133(3) 0.5151(14) 0.030(6) Uiso 1 1 d . . . . .
C14 C 0.70265(18) 0.1986(2) 0.55966(13) 0.0293(4) Uani 1 1 d . . . . .
H14 H 0.7002(19) 0.135(3) 0.6108(15) 0.033(6) Uiso 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C1 2.0327(16) . ?
Fe1 C11 2.0388(18) . ?
Fe1 C5 2.0400(17) . ?
Fe1 C10 2.0415(18) . ?
Fe1 C2 2.0427(16) . ?
Fe1 C14 2.0447(18) . ?
Fe1 C4 2.0496(18) . ?
Fe1 C13 2.0508(17) . ?
Fe1 C12 2.0513(17) . ?
Fe1 C3 2.0515(17) . ?
P1 C7 1.694(2) . ?
P1 N1 1.7130(15) . ?
O1 C8 1.208(2) . ?
N1 N2 1.3684(18) . ?
N1 C8 1.415(2) . ?
C1 C2 1.429(2) . ?
C1 C5 1.431(2) . ?
C1 C6 1.467(2) . ?
N2 C6 1.319(2) . ?
C2 C3 1.419(2) . ?
C2 H2 0.98(2) . ?
C3 C4 1.422(3) . ?
C3 H3 0.97(2) . ?
C4 C5 1.422(3) . ?
C4 H4 0.95(3) . ?
C5 H5 0.91(3) . ?
C6 C7 1.420(2) . ?
C8 C9 1.492(3) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.415(3) . ?
C10 C14 1.416(3) . ?
C10 H10 0.92(3) . ?
C11 C12 1.418(3) . ?
C11 H11 0.93(3) . ?
C12 C13 1.415(3) . ?
C12 H12 0.97(2) . ?
C13 C14 1.421(3) . ?
C13 H13 0.91(2) . ?
C14 H14 0.92(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
C1 Fe1 C11 127.38(7) . . ?
C1 Fe1 C5 41.15(6) . . ?
C11 Fe1 C5 166.47(8) . . ?
C1 Fe1 C10 107.09(7) . . ?
C11 Fe1 C10 40.57(8) . . ?
C5 Fe1 C10 128.74(8) . . ?
C1 Fe1 C2 41.04(6) . . ?
C11 Fe1 C2 106.73(7) . . ?
C5 Fe1 C2 68.96(7) . . ?
C10 Fe1 C2 116.57(8) . . ?
C1 Fe1 C14 117.48(7) . . ?
C11 Fe1 C14 68.29(8) . . ?
C5 Fe1 C14 108.74(8) . . ?
C10 Fe1 C14 40.55(8) . . ?
C2 Fe1 C14 150.48(8) . . ?
C1 Fe1 C4 68.73(7) . . ?
C11 Fe1 C4 151.06(8) . . ?
C5 Fe1 C4 40.69(7) . . ?
C10 Fe1 C4 167.69(8) . . ?
C2 Fe1 C4 68.45(7) . . ?
C14 Fe1 C4 130.03(8) . . ?
C1 Fe1 C13 151.66(7) . . ?
C11 Fe1 C13 68.24(8) . . ?
C5 Fe1 C13 118.74(7) . . ?
C10 Fe1 C13 68.21(8) . . ?
C2 Fe1 C13 166.75(7) . . ?
C14 Fe1 C13 40.61(8) . . ?
C4 Fe1 C13 109.60(8) . . ?
C1 Fe1 C12 166.00(7) . . ?
C11 Fe1 C12 40.58(8) . . ?
C5 Fe1 C12 151.92(7) . . ?
C10 Fe1 C12 68.10(8) . . ?
C2 Fe1 C12 128.05(7) . . ?
C14 Fe1 C12 68.08(8) . . ?
C4 Fe1 C12 118.69(7) . . ?
C13 Fe1 C12 40.37(8) . . ?
C1 Fe1 C3 68.66(7) . . ?
C11 Fe1 C3 117.11(8) . . ?
C5 Fe1 C3 68.56(7) . . ?
C10 Fe1 C3 150.07(8) . . ?
C2 Fe1 C3 40.57(7) . . ?
C14 Fe1 C3 168.12(8) . . ?
C4 Fe1 C3 40.57(8) . . ?
C13 Fe1 C3 129.58(8) . . ?
C12 Fe1 C3 108.50(7) . . ?
C7 P1 N1 87.85(8) . . ?
N2 N1 C8 118.62(14) . . ?
N2 N1 P1 117.09(11) . . ?
C8 N1 P1 124.29(12) . . ?
C2 C1 C5 107.83(14) . . ?
C2 C1 C6 126.43(15) . . ?
C5 C1 C6 125.74(15) . . ?
C2 C1 Fe1 69.85(9) . . ?
C5 C1 Fe1 69.70(9) . . ?
C6 C1 Fe1 126.13(11) . . ?
C6 N2 N1 108.11(13) . . ?
C3 C2 C1 107.95(15) . . ?
C3 C2 Fe1 70.05(10) . . ?
C1 C2 Fe1 69.10(9) . . ?
C3 C2 H2 127.1(13) . . ?
C1 C2 H2 124.9(13) . . ?
Fe1 C2 H2 124.7(13) . . ?
C2 C3 C4 108.22(16) . . ?
C2 C3 Fe1 69.38(9) . . ?
C4 C3 Fe1 69.64(10) . . ?
C2 C3 H3 126.2(13) . . ?
C4 C3 H3 125.6(14) . . ?
Fe1 C3 H3 126.1(14) . . ?
C5 C4 C3 108.27(15) . . ?
C5 C4 Fe1 69.29(10) . . ?
C3 C4 Fe1 69.79(10) . . ?
C5 C4 H4 125.0(15) . . ?
C3 C4 H4 126.7(15) . . ?
Fe1 C4 H4 125.3(15) . . ?
C4 C5 C1 107.73(15) . . ?
C4 C5 Fe1 70.02(10) . . ?
C1 C5 Fe1 69.15(9) . . ?
C4 C5 H5 124.6(15) . . ?
C1 C5 H5 127.6(15) . . ?
Fe1 C5 H5 127.8(15) . . ?
N2 C6 C7 115.85(15) . . ?
N2 C6 C1 118.06(14) . . ?
C7 C6 C1 126.07(15) . . ?
O1 C8 N1 118.29(18) . . ?
O1 C8 C9 124.92(18) . . ?
N1 C8 C9 116.79(15) . . ?
C6 C7 P1 111.11(13) . . ?
C6 C7 H7 124.4 . . ?
P1 C7 H7 124.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C14 108.12(17) . . ?
C11 C10 Fe1 69.61(10) . . ?
C14 C10 Fe1 69.84(11) . . ?
C11 C10 H10 127.1(16) . . ?
C14 C10 H10 124.8(16) . . ?
Fe1 C10 H10 127.7(16) . . ?
C10 C11 C12 107.96(17) . . ?
C10 C11 Fe1 69.82(11) . . ?
C12 C11 Fe1 70.18(10) . . ?
C10 C11 H11 127.3(18) . . ?
C12 C11 H11 124.7(18) . . ?
Fe1 C11 H11 124.1(17) . . ?
C13 C12 C11 108.10(17) . . ?
C13 C12 Fe1 69.80(10) . . ?
C11 C12 Fe1 69.24(10) . . ?
C13 C12 H12 126.2(14) . . ?
C11 C12 H12 125.6(14) . . ?
Fe1 C12 H12 124.7(14) . . ?
C12 C13 C14 107.86(17) . . ?
C12 C13 Fe1 69.84(10) . . ?
C14 C13 Fe1 69.47(10) . . ?
C12 C13 H13 126.1(14) . . ?
C14 C13 H13 126.1(14) . . ?
Fe1 C13 H13 126.6(15) . . ?
C10 C14 C13 107.95(17) . . ?
C10 C14 Fe1 69.60(10) . . ?
C13 C14 Fe1 69.93(10) . . ?
C10 C14 H14 129.0(15) . . ?
C13 C14 H14 123.1(15) . . ?
Fe1 C14 H14 126.2(15) . . ?

_refine_diff_density_max         0.458
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.136


_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_me200622Fe1
_database_code_depnum_ccdc_archive 'CCDC 2053764'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;






_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 Fe N4 P2'
_chemical_formula_weight         354.07

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'
Fe Fe 0.3463 0.8444 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.7557(4)
_cell_length_b                   12.9751(5)
_cell_length_c                   13.2097(6)
_cell_angle_alpha                65.892(2)
_cell_angle_beta                 70.324(2)
_cell_angle_gamma                72.391(2)
_cell_volume                     1410.41(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    52824
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.517
_exptl_crystal_size_mid          0.304
_exptl_crystal_size_min          0.161
_exptl_absorpt_coefficient_mu    1.292
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6268
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.939
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            43018
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.259
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6159
_reflns_number_gt                5149
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0198P)²+1.2850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6159
_refine_ls_number_parameters     395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0606
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.56511(3) 0.26029(2) 0.76663(2) 0.01340(7) Uani 1 1 d . . . . .
N1 N 0.92585(18) 0.38897(14) 0.55353(14) 0.0181(4) Uani 1 1 d . . . . .
P1 P 1.16023(6) 0.22727(5) 0.57185(5) 0.02402(13) Uani 1 1 d . . . . .
C1 C 0.7220(2) 0.29236(16) 0.61400(15) 0.0151(4) Uani 1 1 d . . . . .
C2 C 0.6039(2) 0.39034(17) 0.61321(16) 0.0188(4) Uani 1 1 d . . . . .
H2 H 0.614282 0.468998 0.601682 0.023 Uiso 1 1 calc R U . . .
H2' H 1.113(3) 0.421(2) 0.515(2) 0.022(6) Uiso 1 1 d . . . . .
H2N H 0.596(3) 0.570(2) 0.931(2) 0.024(6) Uiso 1 1 d . . . . .
P2 P 1.07754(6) 0.26162(5) 0.84312(5) 0.02684(13) Uani 1 1 d . . . . .
N2 N 1.07481(19) 0.36549(16) 0.53796(15) 0.0213(4) Uani 1 1 d . . . . .
C3 C 0.4695(2) 0.35616(18) 0.63189(17) 0.0214(4) Uani 1 1 d . . . . .
H3 H 0.368806 0.406608 0.636164 0.026 Uiso 1 1 calc R U . . .
N3 N 0.90827(19) 0.11105(15) 0.92101(14) 0.0208(4) Uani 1 1 d . . . . .
C4 C 0.5023(2) 0.23777(18) 0.64523(17) 0.0215(4) Uani 1 1 d . . . . .
H4 H 0.428897 0.190432 0.660311 0.026 Uiso 1 1 calc R U . . .
H4' H 1.104(3) 0.065(2) 0.928(2) 0.031(7) Uiso 1 1 d . . . . .
H4N H 0.551(3) 0.988(2) 0.578(2) 0.037(8) Uiso 1 1 d . . . . .
N4 N 1.0464(2) 0.12682(17) 0.90391(15) 0.0235(4) Uani 1 1 d . . . . .
C5 C 0.6574(2) 0.19771(17) 0.63506(17) 0.0183(4) Uani 1 1 d . . . . .
H5 H 0.711991 0.117409 0.641270 0.022 Uiso 1 1 calc R U . . .
C6 C 0.8798(2) 0.28910(16) 0.59439(15) 0.0155(4) Uani 1 1 d . . . . .
C7 C 0.9914(2) 0.19051(17) 0.61051(17) 0.0197(4) Uani 1 1 d . . . . .
H7 H 0.975388 0.113915 0.638951 0.024 Uiso 1 1 calc R U . . .
C8 C 0.6678(2) 0.21949(17) 0.89410(16) 0.0175(4) Uani 1 1 d . . . . .
C9 C 0.5542(2) 0.31973(19) 0.89067(17) 0.0211(4) Uani 1 1 d . . . . .
H9 H 0.568451 0.397642 0.877921 0.025 Uiso 1 1 calc R U . . .
C10 C 0.4173(2) 0.2898(2) 0.90805(17) 0.0260(5) Uani 1 1 d . . . . .
H10 H 0.318617 0.343069 0.909716 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4451(2) 0.1716(2) 0.92178(18) 0.0288(5) Uani 1 1 d . . . . .
H11 H 0.369574 0.126934 0.934804 0.035 Uiso 1 1 calc R U . . .
C12 C 0.6003(2) 0.12806(18) 0.91246(17) 0.0235(5) Uani 1 1 d . . . . .
H12 H 0.652458 0.047460 0.917759 0.028 Uiso 1 1 calc R U . . .
C14 C 0.8965(2) 0.30776(18) 0.83712(18) 0.0216(4) Uani 1 1 d . . . . .
H14 H 0.850507 0.385963 0.807507 0.026 Uiso 1 1 calc R U . . .
C13 C 0.8249(2) 0.21385(17) 0.88215(16) 0.0164(4) Uani 1 1 d . . . . .
C1A C 0.2502(2) 0.61070(16) 0.78515(16) 0.0161(4) Uani 1 1 d . . . . .
Fe1A Fe 0.07331(3) 0.74091(2) 0.74677(2) 0.01405(7) Uani 1 1 d . . . . .
P1A P 0.65672(6) 0.65495(5) 0.73950(5) 0.02320(13) Uani 1 1 d . . . . .
N1A N 0.42288(18) 0.58379(14) 0.89167(14) 0.0183(4) Uani 1 1 d . . . . .
C2A C 0.1211(2) 0.59434(18) 0.87810(17) 0.0219(4) Uani 1 1 d . . . . .
H2A H 0.111939 0.589216 0.957654 0.026 Uiso 1 1 calc R U . . .
P2A P 0.48742(6) 0.92590(5) 0.77087(5) 0.02557(13) Uani 1 1 d . . . . .
N2A N 0.56182(19) 0.59791(16) 0.87425(16) 0.0211(4) Uani 1 1 d . . . . .
C3A C 0.0084(2) 0.58606(18) 0.83756(19) 0.0264(5) Uani 1 1 d . . . . .
H3A H -0.094083 0.574507 0.883730 0.032 Uiso 1 1 calc R U . . .
N3A N 0.36893(19) 0.95129(14) 0.61088(14) 0.0202(4) Uani 1 1 d . . . . .
C5A C 0.2147(2) 0.61429(16) 0.68725(17) 0.0189(4) Uani 1 1 d . . . . .
H5A H 0.282627 0.626145 0.609107 0.023 Uiso 1 1 calc R U . . .
C6A C 0.3932(2) 0.62070(16) 0.78965(16) 0.0155(4) Uani 1 1 d . . . . .
C7A C 0.5080(2) 0.66296(17) 0.69459(17) 0.0188(4) Uani 1 1 d . . . . .
H7A H 0.503054 0.691660 0.616986 0.023 Uiso 1 1 calc R U . . .
C8A C 0.1314(2) 0.89400(16) 0.71018(16) 0.0157(4) Uani 1 1 d . . . . .
C9A C 0.0072(2) 0.87489(17) 0.80725(17) 0.0202(4) Uani 1 1 d . . . . .
H9A H 0.003617 0.869280 0.885859 0.024 Uiso 1 1 calc R U . . .
C10A C -0.1097(2) 0.86465(19) 0.77275(19) 0.0250(5) Uani 1 1 d . . . . .
H10A H -0.209777 0.850517 0.822925 0.030 Uiso 1 1 calc R U . . .
C11A C -0.0595(2) 0.87661(17) 0.65534(18) 0.0230(5) Uani 1 1 d . . . . .
H11A H -0.118060 0.872750 0.608171 0.028 Uiso 1 1 calc R U . . .
C12A C 0.0897(2) 0.89451(16) 0.61633(17) 0.0194(4) Uani 1 1 d . . . . .
H12A H 0.153872 0.905376 0.537032 0.023 Uiso 1 1 calc R U . . .
C13A C 0.2727(2) 0.91116(16) 0.71052(16) 0.0162(4) Uani 1 1 d . . . . .
C14A C 0.3177(2) 0.89190(18) 0.80800(18) 0.0207(4) Uani 1 1 d . . . . .
H14A H 0.261132 0.863694 0.884403 0.025 Uiso 1 1 calc R U . . .
C4A C 0.0658(2) 0.59834(17) 0.71987(19) 0.0235(5) Uani 1 1 d . . . . .
H4A H 0.010950 0.596911 0.668858 0.028 Uiso 1 1 calc R U . . .
N4A N 0.4878(2) 0.96333(16) 0.63348(16) 0.0243(4) Uani 1 1 d . . . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C5 2.036(2) . ?
Fe1 C10 2.038(2) . ?
Fe1 C9 2.039(2) . ?
Fe1 C12 2.040(2) . ?
Fe1 C11 2.042(2) . ?
Fe1 C2 2.0430(19) . ?
Fe1 C4 2.046(2) . ?
Fe1 C3 2.048(2) . ?
Fe1 C1 2.0499(19) . ?
Fe1 C8 2.051(2) . ?
N1 C6 1.338(2) . ?
N1 N2 1.352(2) . ?
P1 N2 1.6740(19) . ?
P1 C7 1.706(2) . ?
C1 C2 1.433(3) . ?
C1 C5 1.433(3) . ?
C1 C6 1.464(3) . ?
C2 C3 1.422(3) . ?
C2 H2 1.0000 . ?
P2 N4 1.675(2) . ?
P2 C14 1.703(2) . ?
N2 H2' 0.81(2) . ?
C3 C4 1.419(3) . ?
C3 H3 1.0000 . ?
N3 C13 1.330(2) . ?
N3 N4 1.354(2) . ?
C4 C5 1.422(3) . ?
C4 H4 1.0000 . ?
N4 H4' 0.84(3) . ?
C5 H5 1.0000 . ?
C6 C7 1.399(3) . ?
C7 H7 0.9500 . ?
C8 C12 1.425(3) . ?
C8 C9 1.427(3) . ?
C8 C13 1.469(3) . ?
C9 C10 1.421(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.419(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.428(3) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C14 C13 1.403(3) . ?
C14 H14 0.9500 . ?
C1A C5A 1.428(3) . ?
C1A C2A 1.430(3) . ?
C1A C6A 1.462(3) . ?
C1A Fe1A 2.0532(19) . ?
Fe1A C2A 2.0389(19) . ?
Fe1A C3A 2.041(2) . ?
Fe1A C12A 2.0418(19) . ?
Fe1A C11A 2.043(2) . ?
Fe1A C5A 2.043(2) . ?
Fe1A C9A 2.046(2) . ?
Fe1A C10A 2.046(2) . ?
Fe1A C4A 2.047(2) . ?
Fe1A C8A 2.052(2) . ?
P1A N2A 1.6739(19) . ?
P1A C7A 1.705(2) . ?
N1A C6A 1.334(2) . ?
N1A N2A 1.353(2) . ?
C2A C3A 1.422(3) . ?
C2A H2A 1.0000 . ?
P2A N4A 1.675(2) . ?
P2A C14A 1.702(2) . ?
N2A H2N 0.83(2) . ?
C3A C4A 1.422(3) . ?
C3A H3A 1.0000 . ?
N3A C13A 1.338(2) . ?
N3A N4A 1.356(3) . ?
C5A C4A 1.423(3) . ?
C5A H5A 1.0000 . ?
C6A C7A 1.412(3) . ?
C7A H7A 0.9500 . ?
C8A C12A 1.426(3) . ?
C8A C9A 1.431(3) . ?
C8A C13A 1.463(3) . ?
C9A C10A 1.420(3) . ?
C9A H9A 1.0000 . ?
C10A C11A 1.417(3) . ?
C10A H10A 1.0000 . ?
C11A C12A 1.428(3) . ?
C11A H11A 1.0000 . ?
C12A H12A 1.0000 . ?
C13A C14A 1.402(3) . ?
C14A H14A 0.9500 . ?
C4A H4A 1.0000 . ?
N4A H4N 0.80(3) . ?

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
C5 Fe1 C10 159.18(9) . . ?
C5 Fe1 C9 158.62(8) . . ?
C10 Fe1 C9 40.81(9) . . ?
C5 Fe1 C12 107.30(9) . . ?
C10 Fe1 C12 68.74(9) . . ?
C9 Fe1 C12 68.70(9) . . ?
C5 Fe1 C11 123.00(9) . . ?
C10 Fe1 C11 40.71(10) . . ?
C9 Fe1 C11 68.64(10) . . ?
C12 Fe1 C11 40.97(9) . . ?
C5 Fe1 C2 68.90(8) . . ?
C10 Fe1 C2 121.65(9) . . ?
C9 Fe1 C2 107.51(9) . . ?
C12 Fe1 C2 160.61(8) . . ?
C11 Fe1 C2 157.11(9) . . ?
C5 Fe1 C4 40.76(8) . . ?
C10 Fe1 C4 122.64(9) . . ?
C9 Fe1 C4 159.34(8) . . ?
C12 Fe1 C4 121.80(9) . . ?
C11 Fe1 C4 106.67(9) . . ?
C2 Fe1 C4 68.55(8) . . ?
C5 Fe1 C3 68.55(8) . . ?
C10 Fe1 C3 106.79(9) . . ?
C9 Fe1 C3 123.34(9) . . ?
C12 Fe1 C3 157.32(9) . . ?
C11 Fe1 C3 121.22(9) . . ?
C2 Fe1 C3 40.69(8) . . ?
C4 Fe1 C3 40.55(8) . . ?
C5 Fe1 C1 41.06(8) . . ?
C10 Fe1 C1 158.04(9) . . ?
C9 Fe1 C1 122.45(8) . . ?
C12 Fe1 C1 123.77(8) . . ?
C11 Fe1 C1 160.14(9) . . ?
C2 Fe1 C1 40.99(8) . . ?
C4 Fe1 C1 68.76(8) . . ?
C3 Fe1 C1 68.68(8) . . ?
C5 Fe1 C8 122.50(8) . . ?
C10 Fe1 C8 68.71(8) . . ?
C9 Fe1 C8 40.84(8) . . ?
C12 Fe1 C8 40.77(8) . . ?
C11 Fe1 C8 68.73(9) . . ?
C2 Fe1 C8 124.04(8) . . ?
C4 Fe1 C8 158.08(8) . . ?
C3 Fe1 C8 160.26(9) . . ?
C1 Fe1 C8 107.89(8) . . ?
C6 N1 N2 108.02(16) . . ?
N2 P1 C7 88.37(9) . . ?
C2 C1 C5 107.25(17) . . ?
C2 C1 C6 126.82(18) . . ?
C5 C1 C6 125.92(17) . . ?
C2 C1 Fe1 69.25(11) . . ?
C5 C1 Fe1 68.97(11) . . ?
C6 C1 Fe1 128.02(13) . . ?
C3 C2 C1 108.09(18) . . ?
C3 C2 Fe1 69.83(11) . . ?
C1 C2 Fe1 69.76(10) . . ?
C3 C2 H2 126.0 . . ?
C1 C2 H2 126.0 . . ?
Fe1 C2 H2 126.0 . . ?
N4 P2 C14 88.23(10) . . ?
N1 N2 P1 117.81(14) . . ?
N1 N2 H2' 115.5(17) . . ?
P1 N2 H2' 126.6(17) . . ?
C4 C3 C2 108.29(18) . . ?
C4 C3 Fe1 69.65(11) . . ?
C2 C3 Fe1 69.48(11) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
Fe1 C3 H3 125.9 . . ?
C13 N3 N4 107.80(17) . . ?
C3 C4 C5 108.15(19) . . ?
C3 C4 Fe1 69.80(12) . . ?
C5 C4 Fe1 69.27(12) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe1 C4 H4 125.9 . . ?
N3 N4 P2 117.98(14) . . ?
N3 N4 H4' 112.4(18) . . ?
P2 N4 H4' 129.6(18) . . ?
C4 C5 C1 108.21(18) . . ?
C4 C5 Fe1 69.97(12) . . ?
C1 C5 Fe1 69.97(11) . . ?
C4 C5 H5 125.9 . . ?
C1 C5 H5 125.9 . . ?
Fe1 C5 H5 125.9 . . ?
N1 C6 C7 115.39(18) . . ?
N1 C6 C1 118.27(17) . . ?
C7 C6 C1 126.30(18) . . ?
C6 C7 P1 110.41(15) . . ?
C6 C7 H7 124.8 . . ?
P1 C7 H7 124.8 . . ?
C12 C8 C9 107.60(18) . . ?
C12 C8 C13 127.26(18) . . ?
C9 C8 C13 125.13(19) . . ?
C12 C8 Fe1 69.20(12) . . ?
C9 C8 Fe1 69.12(11) . . ?
C13 C8 Fe1 127.64(13) . . ?
C10 C9 C8 108.21(19) . . ?
C10 C9 Fe1 69.57(12) . . ?
C8 C9 Fe1 70.04(12) . . ?
C10 C9 H9 125.9 . . ?
C8 C9 H9 125.9 . . ?
Fe1 C9 H9 125.9 . . ?
C11 C10 C9 108.17(19) . . ?
C11 C10 Fe1 69.78(12) . . ?
C9 C10 Fe1 69.62(11) . . ?
C11 C10 H10 125.9 . . ?
C9 C10 H10 125.9 . . ?
Fe1 C10 H10 125.9 . . ?
C10 C11 C12 107.9(2) . . ?
C10 C11 Fe1 69.51(12) . . ?
C12 C11 Fe1 69.45(11) . . ?
C10 C11 H11 126.1 . . ?
C12 C11 H11 126.1 . . ?
Fe1 C11 H11 126.1 . . ?
C8 C12 C11 108.1(2) . . ?
C8 C12 Fe1 70.03(11) . . ?
C11 C12 Fe1 69.58(12) . . ?
C8 C12 H12 125.9 . . ?
C11 C12 H12 125.9 . . ?
Fe1 C12 H12 125.9 . . ?
C13 C14 P2 110.35(15) . . ?
C13 C14 H14 124.8 . . ?
P2 C14 H14 124.8 . . ?
N3 C13 C14 115.63(18) . . ?
N3 C13 C8 118.04(18) . . ?
C14 C13 C8 126.28(18) . . ?
C5A C1A C2A 107.54(18) . . ?
C5A C1A C6A 126.13(18) . . ?
C2A C1A C6A 126.33(18) . . ?
C5A C1A Fe1A 69.21(11) . . ?
C2A C1A Fe1A 69.00(11) . . ?
C6A C1A Fe1A 127.60(14) . . ?
C2A Fe1A C3A 40.79(9) . . ?
C2A Fe1A C12A 161.25(9) . . ?
C3A Fe1A C12A 156.76(9) . . ?
C2A Fe1A C11A 156.33(9) . . ?
C3A Fe1A C11A 120.69(9) . . ?
C12A Fe1A C11A 40.93(8) . . ?
C2A Fe1A C5A 68.79(8) . . ?
C3A Fe1A C5A 68.53(9) . . ?
C12A Fe1A C5A 107.77(8) . . ?
C11A Fe1A C5A 123.84(8) . . ?
C2A Fe1A C9A 107.36(9) . . ?
C3A Fe1A C9A 123.46(9) . . ?
C12A Fe1A C9A 68.60(8) . . ?
C11A Fe1A C9A 68.42(9) . . ?
C5A Fe1A C9A 158.19(8) . . ?
C2A Fe1A C10A 121.11(9) . . ?
C3A Fe1A C10A 106.65(9) . . ?
C12A Fe1A C10A 68.55(8) . . ?
C11A Fe1A C10A 40.54(9) . . ?
C5A Fe1A C10A 159.95(9) . . ?
C9A Fe1A C10A 40.62(9) . . ?
C2A Fe1A C4A 68.71(9) . . ?
C3A Fe1A C4A 40.71(9) . . ?
C12A Fe1A C4A 121.51(9) . . ?
C11A Fe1A C4A 106.76(9) . . ?
C5A Fe1A C4A 40.72(8) . . ?
C9A Fe1A C4A 159.74(9) . . ?
C10A Fe1A C4A 123.07(9) . . ?
C2A Fe1A C8A 124.32(8) . . ?
C3A Fe1A C8A 160.65(9) . . ?
C12A Fe1A C8A 40.76(8) . . ?
C11A Fe1A C8A 68.69(8) . . ?
C5A Fe1A C8A 122.35(8) . . ?
C9A Fe1A C8A 40.88(8) . . ?
C10A Fe1A C8A 68.60(8) . . ?
C4A Fe1A C8A 157.60(8) . . ?
C2A Fe1A C1A 40.92(8) . . ?
C3A Fe1A C1A 68.59(8) . . ?
C12A Fe1A C1A 124.56(8) . . ?
C11A Fe1A C1A 161.03(8) . . ?
C5A Fe1A C1A 40.80(8) . . ?
C9A Fe1A C1A 122.30(8) . . ?
C10A Fe1A C1A 157.41(9) . . ?
C4A Fe1A C1A 68.60(8) . . ?
C8A Fe1A C1A 108.18(8) . . ?
N2A P1A C7A 88.46(9) . . ?
C6A N1A N2A 107.83(16) . . ?
C3A C2A C1A 107.95(19) . . ?
C3A C2A Fe1A 69.68(11) . . ?
C1A C2A Fe1A 70.08(11) . . ?
C3A C2A H2A 126.0 . . ?
C1A C2A H2A 126.0 . . ?
Fe1A C2A H2A 126.0 . . ?
N4A P2A C14A 88.35(10) . . ?
N1A N2A P1A 118.15(14) . . ?
N1A N2A H2N 116.3(17) . . ?
P1A N2A H2N 125.2(17) . . ?
C4A C3A C2A 108.36(19) . . ?
C4A C3A Fe1A 69.87(12) . . ?
C2A C3A Fe1A 69.53(12) . . ?
C4A C3A H3A 125.8 . . ?
C2A C3A H3A 125.8 . . ?
Fe1A C3A H3A 125.8 . . ?
C13A N3A N4A 108.14(17) . . ?
C4A C5A C1A 108.30(18) . . ?
C4A C5A Fe1A 69.79(12) . . ?
C1A C5A Fe1A 70.00(11) . . ?
C4A C5A H5A 125.8 . . ?
C1A C5A H5A 125.8 . . ?
Fe1A C5A H5A 125.8 . . ?
N1A C6A C7A 115.52(18) . . ?
N1A C6A C1A 118.45(17) . . ?
C7A C6A C1A 126.00(18) . . ?
C6A C7A P1A 110.04(15) . . ?
C6A C7A H7A 125.0 . . ?
P1A C7A H7A 125.0 . . ?
C12A C8A C9A 107.45(18) . . ?
C12A C8A C13A 127.76(18) . . ?
C9A C8A C13A 124.78(18) . . ?
C12A C8A Fe1A 69.22(11) . . ?
C9A C8A Fe1A 69.32(12) . . ?
C13A C8A Fe1A 127.40(13) . . ?
C10A C9A C8A 108.17(18) . . ?
C10A C9A Fe1A 69.69(12) . . ?
C8A C9A Fe1A 69.80(11) . . ?
C10A C9A H9A 125.9 . . ?
C8A C9A H9A 125.9 . . ?
Fe1A C9A H9A 125.9 . . ?
C11A C10A C9A 108.26(19) . . ?
C11A C10A Fe1A 69.61(12) . . ?
C9A C10A Fe1A 69.69(11) . . ?
C11A C10A H10A 125.9 . . ?
C9A C10A H10A 125.9 . . ?
Fe1A C10A H10A 125.9 . . ?
C10A C11A C12A 108.02(19) . . ?
C10A C11A Fe1A 69.84(12) . . ?
C12A C11A Fe1A 69.49(11) . . ?
C10A C11A H11A 126.0 . . ?
C12A C11A H11A 126.0 . . ?
Fe1A C11A H11A 126.0 . . ?
C8A C12A C11A 108.10(18) . . ?
C8A C12A Fe1A 70.02(11) . . ?
C11A C12A Fe1A 69.58(11) . . ?
C8A C12A H12A 126.0 . . ?
C11A C12A H12A 126.0 . . ?
Fe1A C12A H12A 126.0 . . ?
N3A C13A C14A 115.04(19) . . ?
N3A C13A C8A 119.27(18) . . ?
C14A C13A C8A 125.67(18) . . ?
C13A C14A P2A 110.78(15) . . ?
C13A C14A H14A 124.6 . . ?
P2A C14A H14A 124.6 . . ?
C3A C4A C5A 107.84(19) . . ?
C3A C4A Fe1A 69.42(13) . . ?
C5A C4A Fe1A 69.49(12) . . ?
C3A C4A H4A 126.1 . . ?
C5A C4A H4A 126.1 . . ?
Fe1A C4A H4A 126.1 . . ?
N3A N4A P2A 117.69(14) . . ?
N3A N4A H4N 115(2) . . ?
P2A N4A H4N 128(2) . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_me201001As1
_database_code_depnum_ccdc_archive 'CCDC 2055302'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2021-01-11 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 As Fe N2 O'
_chemical_formula_weight         356.03

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'
As As 0.0499 2.0058 '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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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'

_cell_length_a                   11.5955(13)
_cell_length_b                   7.3503(8)
_cell_length_c                   15.4894(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.284(4)
_cell_angle_gamma                90
_cell_volume                     1319.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    25512
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.793
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.507
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_min          0.134
_exptl_absorpt_coefficient_mu    3.624
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3872
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.512
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            25512
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.153
_diffrn_reflns_theta_max         27.598
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3058
_reflns_number_gt                2535
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0116P)²+5.5142P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3058
_refine_ls_number_parameters     173
_refine_ls_number_restraints     237
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
As1 As 0.46647(4) 0.43625(6) 0.80435(3) 0.02779(13) Uani 1 1 d . U . . .
Fe1 Fe 0.76452(5) 0.54250(7) 0.54418(3) 0.01489(13) Uani 1 1 d . U . . .
O1 O 0.3015(3) 0.1144(4) 0.7798(2) 0.0349(7) Uani 1 1 d . U . . .
N1 N 0.4654(3) 0.2343(4) 0.7324(2) 0.0184(6) Uani 1 1 d . U . . .
C1 C 0.7298(3) 0.3600(5) 0.6384(2) 0.0149(7) Uani 1 1 d . U . . .
N2 N 0.5542(3) 0.2186(4) 0.67869(19) 0.0162(6) Uani 1 1 d . U . . .
C2 C 0.8344(3) 0.4569(5) 0.6596(3) 0.0204(7) Uani 1 1 d . U . . .
H2 H 0.8493 0.5344 0.7120 0.024 Uiso 1 1 calc R U . . .
C3 C 0.9131(3) 0.4242(5) 0.5934(3) 0.0246(8) Uani 1 1 d . U . . .
H3 H 0.9928 0.4752 0.5906 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8574(4) 0.3071(5) 0.5310(3) 0.0237(8) Uani 1 1 d . U . . .
H4 H 0.8913 0.2625 0.4765 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7452(3) 0.2685(5) 0.5585(2) 0.0173(7) Uani 1 1 d . U . . .
H5 H 0.6864 0.1910 0.5271 0.021 Uiso 1 1 calc R U . . .
C6 C 0.6179(4) 0.6917(5) 0.5212(3) 0.0299(9) Uani 1 1 d . U . . .
H6 H 0.5410 0.6679 0.5461 0.036 Uiso 1 1 calc R U . . .
C8 C 0.8002(4) 0.8008(5) 0.5028(3) 0.0251(9) Uani 1 1 d . U . . .
H8 H 0.8750 0.8671 0.5123 0.030 Uiso 1 1 calc R U . . .
C7 C 0.7061(4) 0.8035(5) 0.5581(3) 0.0288(9) Uani 1 1 d . U . . .
H7 H 0.7027 0.8721 0.6137 0.035 Uiso 1 1 calc R U . . .
C9 C 0.7698(4) 0.6869(5) 0.4315(3) 0.0246(8) Uani 1 1 d . U . . .
H9 H 0.8194 0.6590 0.3818 0.030 Uiso 1 1 calc R U . . .
C10 C 0.6575(4) 0.6189(5) 0.4434(3) 0.0272(9) Uani 1 1 d . U . . .
H10 H 0.6134 0.5351 0.4033 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6270(3) 0.3575(5) 0.6900(2) 0.0153(7) Uani 1 1 d . U . . .
C12 C 0.5996(4) 0.4891(5) 0.7524(3) 0.0230(8) Uani 1 1 d . U . . .
H12 H 0.6456 0.5931 0.7656 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3790(3) 0.1001(5) 0.7305(3) 0.0240(8) Uani 1 1 d . U . . .
C14 C 0.3922(4) -0.0527(6) 0.6679(3) 0.0301(9) Uani 1 1 d . U . . .
H14A H 0.3922 -0.0040 0.6090 0.045 Uiso 1 1 calc R U . . .
H14B H 0.3279 -0.1381 0.6728 0.045 Uiso 1 1 calc R U . . .
H14C H 0.4652 -0.1161 0.6810 0.045 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
As1 C12 1.811(4) . ?
As1 N1 1.856(3) . ?
Fe1 C2 2.033(4) . ?
Fe1 C1 2.035(3) . ?
Fe1 C10 2.035(4) . ?
Fe1 C5 2.040(3) . ?
Fe1 C6 2.043(4) . ?
Fe1 C9 2.046(4) . ?
Fe1 C7 2.049(4) . ?
Fe1 C3 2.049(4) . ?
Fe1 C8 2.052(4) . ?
Fe1 C4 2.052(4) . ?
O1 C13 1.208(5) . ?
N1 N2 1.354(4) . ?
N1 C13 1.405(5) . ?
C1 C5 1.426(5) . ?
C1 C2 1.434(5) . ?
C1 C11 1.461(5) . ?
N2 C11 1.332(5) . ?
C2 C3 1.421(6) . ?
C2 H2 1.0000 . ?
C3 C4 1.429(6) . ?
C3 H3 1.0000 . ?
C4 C5 1.415(5) . ?
C4 H4 1.0000 . ?
C5 H5 1.0000 . ?
C6 C10 1.413(6) . ?
C6 C7 1.415(6) . ?
C6 H6 1.0000 . ?
C8 C7 1.415(6) . ?
C8 C9 1.419(6) . ?
C8 H8 1.0000 . ?
C7 H7 1.0000 . ?
C9 C10 1.414(6) . ?
C9 H9 1.0000 . ?
C10 H10 1.0000 . ?
C11 C12 1.413(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.495(6) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C12 As1 N1 83.71(16) . . ?
C2 Fe1 C1 41.28(14) . . ?
C2 Fe1 C10 165.88(17) . . ?
C1 Fe1 C10 126.88(16) . . ?
C2 Fe1 C5 68.93(15) . . ?
C1 Fe1 C5 40.96(14) . . ?
C10 Fe1 C5 106.83(16) . . ?
C2 Fe1 C6 128.24(17) . . ?
C1 Fe1 C6 106.96(16) . . ?
C10 Fe1 C6 40.54(18) . . ?
C5 Fe1 C6 117.04(17) . . ?
C2 Fe1 C9 152.43(17) . . ?
C1 Fe1 C9 165.39(16) . . ?
C10 Fe1 C9 40.56(17) . . ?
C5 Fe1 C9 127.77(16) . . ?
C6 Fe1 C9 68.03(17) . . ?
C2 Fe1 C7 108.58(17) . . ?
C1 Fe1 C7 117.78(16) . . ?
C10 Fe1 C7 68.20(18) . . ?
C5 Fe1 C7 151.03(17) . . ?
C6 Fe1 C7 40.47(18) . . ?
C9 Fe1 C7 68.01(17) . . ?
C2 Fe1 C3 40.73(16) . . ?
C1 Fe1 C3 68.97(15) . . ?
C10 Fe1 C3 151.70(17) . . ?
C5 Fe1 C3 68.60(16) . . ?
C6 Fe1 C3 166.95(18) . . ?
C9 Fe1 C3 118.95(17) . . ?
C7 Fe1 C3 129.39(18) . . ?
C2 Fe1 C8 118.88(16) . . ?
C1 Fe1 C8 151.98(16) . . ?
C10 Fe1 C8 68.24(17) . . ?
C5 Fe1 C8 166.50(16) . . ?
C6 Fe1 C8 68.01(17) . . ?
C9 Fe1 C8 40.52(17) . . ?
C7 Fe1 C8 40.36(17) . . ?
C3 Fe1 C8 109.38(17) . . ?
C2 Fe1 C4 68.58(16) . . ?
C1 Fe1 C4 68.61(15) . . ?
C10 Fe1 C4 117.54(17) . . ?
C5 Fe1 C4 40.44(15) . . ?
C6 Fe1 C4 150.65(18) . . ?
C9 Fe1 C4 108.57(16) . . ?
C7 Fe1 C4 167.64(18) . . ?
C3 Fe1 C4 40.79(17) . . ?
C8 Fe1 C4 129.48(17) . . ?
N2 N1 C13 119.0(3) . . ?
N2 N1 As1 116.8(2) . . ?
C13 N1 As1 124.2(3) . . ?
C5 C1 C2 107.4(3) . . ?
C5 C1 C11 127.0(3) . . ?
C2 C1 C11 125.6(3) . . ?
C5 C1 Fe1 69.7(2) . . ?
C2 C1 Fe1 69.3(2) . . ?
C11 C1 Fe1 126.1(2) . . ?
C11 N2 N1 110.3(3) . . ?
C3 C2 C1 108.2(3) . . ?
C3 C2 Fe1 70.2(2) . . ?
C1 C2 Fe1 69.4(2) . . ?
C3 C2 H2 125.9 . . ?
C1 C2 H2 125.9 . . ?
Fe1 C2 H2 125.9 . . ?
C2 C3 C4 107.7(4) . . ?
C2 C3 Fe1 69.0(2) . . ?
C4 C3 Fe1 69.7(2) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
Fe1 C3 H3 126.1 . . ?
C5 C4 C3 108.3(4) . . ?
C5 C4 Fe1 69.3(2) . . ?
C3 C4 Fe1 69.5(2) . . ?
C5 C4 H4 125.9 . . ?
C3 C4 H4 125.9 . . ?
Fe1 C4 H4 125.9 . . ?
C4 C5 C1 108.4(3) . . ?
C4 C5 Fe1 70.3(2) . . ?
C1 C5 Fe1 69.32(19) . . ?
C4 C5 H5 125.8 . . ?
C1 C5 H5 125.8 . . ?
Fe1 C5 H5 125.8 . . ?
C10 C6 C7 108.1(4) . . ?
C10 C6 Fe1 69.4(2) . . ?
C7 C6 Fe1 70.0(2) . . ?
C10 C6 H6 125.9 . . ?
C7 C6 H6 125.9 . . ?
Fe1 C6 H6 125.9 . . ?
C7 C8 C9 107.8(4) . . ?
C7 C8 Fe1 69.7(2) . . ?
C9 C8 Fe1 69.5(2) . . ?
C7 C8 H8 126.1 . . ?
C9 C8 H8 126.1 . . ?
Fe1 C8 H8 126.1 . . ?
C8 C7 C6 108.0(4) . . ?
C8 C7 Fe1 69.9(2) . . ?
C6 C7 Fe1 69.5(2) . . ?
C8 C7 H7 126.0 . . ?
C6 C7 H7 126.0 . . ?
Fe1 C7 H7 126.0 . . ?
C10 C9 C8 108.0(4) . . ?
C10 C9 Fe1 69.3(2) . . ?
C8 C9 Fe1 70.0(2) . . ?
C10 C9 H9 126.0 . . ?
C8 C9 H9 126.0 . . ?
Fe1 C9 H9 126.0 . . ?
C6 C10 C9 108.0(4) . . ?
C6 C10 Fe1 70.0(2) . . ?
C9 C10 Fe1 70.1(2) . . ?
C6 C10 H10 126.0 . . ?
C9 C10 H10 126.0 . . ?
Fe1 C10 H10 126.0 . . ?
N2 C11 C12 117.2(3) . . ?
N2 C11 C1 117.7(3) . . ?
C12 C11 C1 125.2(3) . . ?
C11 C12 As1 112.1(3) . . ?
C11 C12 H12 124.0 . . ?
As1 C12 H12 124.0 . . ?
O1 C13 N1 118.3(4) . . ?
O1 C13 C14 125.0(4) . . ?
N1 C13 C14 116.7(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.690
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.112

####################################################################### 
# 
# 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_me200504Fe1
_database_code_depnum_ccdc_archive 'CCDC 2053761'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice, Faculty of Chemical Technology, Pardubice
Czech Republic
;
_audit_update_record             
;
2021-01-04 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 Fe N4 O2 P2'
_chemical_formula_weight         438.14

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'
Fe Fe 0.3463 0.8444 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   8.8683(7)
_cell_length_b                   9.7413(7)
_cell_length_c                   21.2822(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1838.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14825
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.016
_exptl_absorpt_coefficient_mu    1.016
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5355
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.718
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            14825
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0759
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.835
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2118
_reflns_number_gt                1621
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0321P)²+0.9871P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2118
_refine_ls_number_parameters     124
_refine_ls_number_restraints     117
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0813
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.7500 0.7500 0.81702(2) 0.01312(12) Uani 1 2 d S TU P . .
P1 P 0.47834(8) 0.77436(6) 0.59766(3) 0.02562(17) Uani 1 1 d . U . . .
O1 O 0.6136(2) 0.62284(19) 0.49117(8) 0.0356(5) Uani 1 1 d . U . . .
N1 N 0.6379(2) 0.58090(19) 0.65337(8) 0.0171(4) Uani 1 1 d . U . . .
C1 C 0.6136(3) 0.6279(2) 0.76375(10) 0.0154(5) Uani 1 1 d . U . . .
N2 N 0.5937(2) 0.63343(18) 0.59664(8) 0.0182(4) Uani 1 1 d . U . . .
C2 C 0.5344(3) 0.6777(2) 0.81778(10) 0.0206(5) Uani 1 1 d . U . . .
H2 H 0.4405 0.7345 0.8175 0.025 Uiso 1 1 calc R U . . .
C3 C 0.6136(3) 0.6315(2) 0.87207(11) 0.0243(5) Uani 1 1 d . U . . .
H3 H 0.5853 0.6512 0.9166 0.029 Uiso 1 1 calc R U . . .
C4 C 0.7399(3) 0.5548(2) 0.85228(10) 0.0231(5) Uani 1 1 d . U . . .
H4 H 0.8164 0.5113 0.8805 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7414(3) 0.5518(2) 0.78531(10) 0.0187(5) Uani 1 1 d . U . . .
H5 H 0.8183 0.5053 0.7583 0.022 Uiso 1 1 calc R U . . .
C6 C 0.5772(3) 0.6582(2) 0.69784(9) 0.0155(5) Uani 1 1 d . U . . .
C8 C 0.6451(3) 0.5703(3) 0.54070(11) 0.0249(6) Uani 1 1 d . U . . .
C7 C 0.4859(3) 0.7676(2) 0.67690(11) 0.0243(5) Uani 1 1 d . U . . .
H7 H 0.4350 0.8297 0.7040 0.029 Uiso 1 1 calc R U . . .
C9 C 0.7334(3) 0.4405(3) 0.54832(12) 0.0376(7) Uani 1 1 d . U . . .
H9A H 0.6677 0.3686 0.5653 0.056 Uiso 1 1 calc R U . . .
H9B H 0.8175 0.4564 0.5773 0.056 Uiso 1 1 calc R U . . .
H9C H 0.7727 0.4115 0.5074 0.056 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C2 2.038(2) . ?
Fe1 C2 2.038(2) 2_665 ?
Fe1 C1 2.040(2) 2_665 ?
Fe1 C1 2.040(2) . ?
Fe1 C3 2.042(2) . ?
Fe1 C3 2.042(2) 2_665 ?
Fe1 C4 2.046(2) . ?
Fe1 C4 2.046(2) 2_665 ?
Fe1 C5 2.047(2) . ?
Fe1 C5 2.047(2) 2_665 ?
P1 C7 1.689(2) . ?
P1 N2 1.712(2) . ?
O1 C8 1.204(3) . ?
N1 C6 1.324(3) . ?
N1 N2 1.369(2) . ?
C1 C5 1.430(3) . ?
C1 C2 1.432(3) . ?
C1 C6 1.469(3) . ?
N2 C8 1.415(3) . ?
C2 C3 1.425(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.410(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.426(3) . ?
C4 H4 1.0000 . ?
C5 H5 1.0000 . ?
C6 C7 1.410(3) . ?
C8 C9 1.496(4) . ?
C7 H7 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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 179.09(12) . 2_665 ?
C2 Fe1 C1 139.65(9) . 2_665 ?
C2 Fe1 C1 41.12(9) 2_665 2_665 ?
C2 Fe1 C1 41.12(9) . . ?
C2 Fe1 C1 139.65(9) 2_665 . ?
C1 Fe1 C1 112.49(12) 2_665 . ?
C2 Fe1 C3 40.90(10) . . ?
C2 Fe1 C3 138.31(10) 2_665 . ?
C1 Fe1 C3 178.55(9) 2_665 . ?
C1 Fe1 C3 68.78(9) . . ?
C2 Fe1 C3 138.31(10) . 2_665 ?
C2 Fe1 C3 40.90(10) 2_665 2_665 ?
C1 Fe1 C3 68.78(9) 2_665 2_665 ?
C1 Fe1 C3 178.55(9) . 2_665 ?
C3 Fe1 C3 109.96(13) . 2_665 ?
C2 Fe1 C4 68.58(11) . . ?
C2 Fe1 C4 111.06(10) 2_665 . ?
C1 Fe1 C4 140.49(10) 2_665 . ?
C1 Fe1 C4 68.66(9) . . ?
C3 Fe1 C4 40.37(10) . . ?
C3 Fe1 C4 109.94(10) 2_665 . ?
C2 Fe1 C4 111.06(11) . 2_665 ?
C2 Fe1 C4 68.58(11) 2_665 2_665 ?
C1 Fe1 C4 68.66(9) 2_665 2_665 ?
C1 Fe1 C4 140.49(10) . 2_665 ?
C3 Fe1 C4 109.94(10) . 2_665 ?
C3 Fe1 C4 40.37(10) 2_665 2_665 ?
C4 Fe1 C4 136.97(12) . 2_665 ?
C2 Fe1 C5 69.01(10) . . ?
C2 Fe1 C5 111.31(10) 2_665 . ?
C1 Fe1 C5 112.88(9) 2_665 . ?
C1 Fe1 C5 40.97(9) . . ?
C3 Fe1 C5 68.52(9) . . ?
C3 Fe1 C5 138.12(10) 2_665 . ?
C4 Fe1 C5 40.77(8) . . ?
C4 Fe1 C5 177.69(9) 2_665 . ?
C2 Fe1 C5 111.31(10) . 2_665 ?
C2 Fe1 C5 69.01(10) 2_665 2_665 ?
C1 Fe1 C5 40.96(9) 2_665 2_665 ?
C1 Fe1 C5 112.88(9) . 2_665 ?
C3 Fe1 C5 138.12(10) . 2_665 ?
C3 Fe1 C5 68.52(9) 2_665 2_665 ?
C4 Fe1 C5 177.70(9) . 2_665 ?
C4 Fe1 C5 40.77(8) 2_665 2_665 ?
C5 Fe1 C5 141.50(12) . 2_665 ?
C7 P1 N2 87.56(10) . . ?
C6 N1 N2 107.54(18) . . ?
C5 C1 C2 107.87(19) . . ?
C5 C1 C6 125.77(19) . . ?
C2 C1 C6 126.2(2) . . ?
C5 C1 Fe1 69.77(12) . . ?
C2 C1 Fe1 69.34(12) . . ?
C6 C1 Fe1 122.95(15) . . ?
N1 N2 C8 119.15(19) . . ?
N1 N2 P1 117.38(14) . . ?
C8 N2 P1 123.46(16) . . ?
C3 C2 C1 107.6(2) . . ?
C3 C2 Fe1 69.71(14) . . ?
C1 C2 Fe1 69.54(13) . . ?
C3 C2 H2 126.2 . . ?
C1 C2 H2 126.2 . . ?
Fe1 C2 H2 126.2 . . ?
C4 C3 C2 108.5(2) . . ?
C4 C3 Fe1 69.98(13) . . ?
C2 C3 Fe1 69.40(13) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
Fe1 C3 H3 125.8 . . ?
C3 C4 C5 108.5(2) . . ?
C3 C4 Fe1 69.65(13) . . ?
C5 C4 Fe1 69.65(12) . . ?
C3 C4 H4 125.7 . . ?
C5 C4 H4 125.7 . . ?
Fe1 C4 H4 125.7 . . ?
C4 C5 C1 107.6(2) . . ?
C4 C5 Fe1 69.58(13) . . ?
C1 C5 Fe1 69.26(12) . . ?
C4 C5 H5 126.2 . . ?
C1 C5 H5 126.2 . . ?
Fe1 C5 H5 126.2 . . ?
N1 C6 C7 115.93(19) . . ?
N1 C6 C1 118.62(19) . . ?
C7 C6 C1 125.40(19) . . ?
O1 C8 N2 118.5(2) . . ?
O1 C8 C9 125.1(2) . . ?
N2 C8 C9 116.4(2) . . ?
C6 C7 P1 111.58(17) . . ?
C6 C7 H7 124.2 . . ?
P1 C7 H7 124.2 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.075


_exptl_crystal_recrystallization_method Sublimation
####################################################################### 
# 
# 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_me190110As2
_database_code_depnum_ccdc_archive 'CCDC 2053766'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Fe N2 O'
_chemical_formula_weight         284.14

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'
Fe Fe 0.3463 0.8444 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.7872(5)
_cell_length_b                   12.8584(5)
_cell_length_c                   20.2069(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2543.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    28543
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.484
_exptl_crystal_size_mid          0.222
_exptl_crystal_size_min          0.157
_exptl_absorpt_coefficient_mu    1.174
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5698
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.763
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            24400
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.312
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5560
_reflns_number_gt                4644
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.999

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0234P)²+0.8259P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1757 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5560
_refine_ls_number_parameters     332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0674
_refine_ls_wR_factor_gt          0.0636
_refine_ls_goodness_of_fit_ref   0.981
_refine_ls_restrained_S_all      0.981
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.66903(5) 0.61868(4) 0.97829(3) 0.01193(13) Uani 1 1 d . . . . .
N1' N 0.6548(4) 0.5729(3) 0.78288(15) 0.0169(7) Uani 1 1 d . . . . .
O1 O 0.5643(3) 0.6139(2) 0.61722(13) 0.0229(7) Uani 1 1 d . . . . .
C1 C 0.7458(4) 0.5716(3) 0.88979(19) 0.0137(9) Uani 1 1 d . . . . .
Fe2 Fe 0.63755(6) 0.83425(4) 0.31467(3) 0.01480(14) Uani 1 1 d . . . . .
N2' N 0.6327(3) 0.6232(3) 0.72296(14) 0.0181(7) Uani 1 1 d . . . . .
H2' H 0.653168 0.689562 0.718704 0.022 Uiso 1 1 calc R U . . .
O2 O 0.7223(3) 0.8350(3) 0.68206(14) 0.0308(7) Uani 1 1 d . . . . .
C2 C 0.8549(4) 0.5964(3) 0.93454(17) 0.0134(8) Uani 1 1 d . . . . .
H2A H 0.926454 0.650789 0.927521 0.016 Uiso 1 1 calc R U . . .
C4 C 0.7274(4) 0.4659(3) 0.9814(2) 0.0183(9) Uani 1 1 d . . . . .
H4 H 0.693144 0.412595 1.013399 0.022 Uiso 1 1 calc R U . . .
N4' N 0.6555(4) 0.8285(3) 0.57625(15) 0.0165(7) Uani 1 1 d . . . . .
H4' H 0.614(4) 0.771(3) 0.582(2) 0.020 Uiso 1 1 d . U . . .
C3 C 0.8431(4) 0.5306(3) 0.99068(18) 0.0174(9) Uani 1 1 d . . . . .
H3 H 0.904164 0.531187 1.030354 0.021 Uiso 1 1 calc R U . . .
N3' N 0.6520(3) 0.8769(3) 0.51457(14) 0.0163(7) Uani 1 1 d . . . . .
C5 C 0.6662(4) 0.4910(3) 0.91892(18) 0.0146(9) Uani 1 1 d . . . . .
H5 H 0.583338 0.457614 0.899253 0.018 Uiso 1 1 calc R U . . .
C6 C 0.7204(4) 0.6247(3) 0.82714(18) 0.0136(8) Uani 1 1 d . . . . .
C7 C 0.7722(5) 0.7340(3) 0.8178(2) 0.0232(10) Uani 1 1 d . . . . .
H7A H 0.836629 0.735705 0.780757 0.035 Uiso 1 1 calc R U . . .
H7B H 0.818427 0.756997 0.858287 0.035 Uiso 1 1 calc R U . . .
H7C H 0.695130 0.780391 0.808445 0.035 Uiso 1 1 calc R U . . .
C8 C 0.5799(4) 0.5701(3) 0.6713(2) 0.0194(10) Uani 1 1 d . . . . .
C9 C 0.5423(5) 0.4592(3) 0.6819(2) 0.0327(12) Uani 1 1 d . . . . .
H9A H 0.499650 0.431587 0.641701 0.049 Uiso 1 1 calc R U . . .
H9B H 0.477923 0.454091 0.718879 0.049 Uiso 1 1 calc R U . . .
H9C H 0.624713 0.418971 0.692085 0.049 Uiso 1 1 calc R U . . .
C10 C 0.5140(4) 0.7200(3) 0.9591(2) 0.0226(11) Uani 1 1 d . . . . .
H10 H 0.471031 0.732975 0.914925 0.027 Uiso 1 1 calc R U . . .
C11 C 0.6280(5) 0.7735(3) 0.9857(2) 0.0225(10) Uani 1 1 d . . . . .
H11 H 0.679875 0.830889 0.963667 0.027 Uiso 1 1 calc R U . . .
C12 C 0.6556(5) 0.7314(3) 1.0497(2) 0.0207(10) Uani 1 1 d . . . . .
H12 H 0.730492 0.753615 1.080196 0.025 Uiso 1 1 calc R U . . .
C13 C 0.5588(4) 0.6518(3) 1.0619(2) 0.0200(10) Uani 1 1 d . . . . .
H13 H 0.553767 0.607668 1.102594 0.024 Uiso 1 1 calc R U . . .
C14 C 0.4716(4) 0.6446(3) 1.0064(2) 0.0211(10) Uani 1 1 d . . . . .
H14 H 0.393831 0.594805 1.001078 0.025 Uiso 1 1 calc R U . . .
C15 C 0.5757(4) 0.8880(3) 0.40540(19) 0.0149(9) Uani 1 1 d . . . . .
C16 C 0.6813(5) 0.9524(3) 0.37944(19) 0.0181(10) Uani 1 1 d . . . . .
H16 H 0.771885 0.965982 0.400607 0.022 Uiso 1 1 calc R U . . .
C17 C 0.6361(4) 0.9927(3) 0.3176(2) 0.0194(9) Uani 1 1 d . . . . .
H17 H 0.689027 1.040045 0.287880 0.023 Uiso 1 1 calc R U . . .
C18 C 0.5014(5) 0.9541(3) 0.3056(2) 0.0208(10) Uani 1 1 d . . . . .
H18 H 0.444078 0.969353 0.265772 0.025 Uiso 1 1 calc R U . . .
C19 C 0.4644(4) 0.8888(3) 0.35871(19) 0.0175(9) Uani 1 1 d . . . . .
H19 H 0.376143 0.850260 0.363332 0.021 Uiso 1 1 calc R U . . .
C20 C 0.5775(4) 0.8339(3) 0.46985(19) 0.0146(8) Uani 1 1 d . . . . .
C21 C 0.4927(4) 0.7375(3) 0.4790(2) 0.0233(10) Uani 1 1 d . . . . .
H21A H 0.443266 0.722320 0.437950 0.035 Uiso 1 1 calc R U . . .
H21B H 0.427178 0.748566 0.514973 0.035 Uiso 1 1 calc R U . . .
H21C H 0.552452 0.678858 0.490014 0.035 Uiso 1 1 calc R U . . .
C22 C 0.7174(4) 0.8774(4) 0.6273(2) 0.0203(9) Uani 1 1 d . . . . .
C23 C 0.7796(5) 0.9824(4) 0.6152(2) 0.0358(13) Uani 1 1 d . . . . .
H23A H 0.846384 0.977475 0.579201 0.054 Uiso 1 1 calc R U . . .
H23B H 0.825327 1.006394 0.655552 0.054 Uiso 1 1 calc R U . . .
H23C H 0.707703 1.031809 0.602970 0.054 Uiso 1 1 calc R U . . .
C24 C 0.6888(5) 0.6809(3) 0.3233(2) 0.0274(11) Uani 1 1 d . . . . .
H24 H 0.676658 0.637241 0.363825 0.033 Uiso 1 1 calc R U . . .
C25 C 0.8052(5) 0.7396(3) 0.3077(2) 0.0288(11) Uani 1 1 d . . . . .
H25 H 0.890022 0.744859 0.335146 0.035 Uiso 1 1 calc R U . . .
C26 C 0.7810(5) 0.7916(4) 0.2464(2) 0.0299(12) Uani 1 1 d . . . . .
H26 H 0.845763 0.839036 0.222863 0.036 Uiso 1 1 calc R U . . .
C27 C 0.6475(5) 0.7630(3) 0.2250(2) 0.0281(11) Uani 1 1 d . . . . .
H27 H 0.601673 0.787300 0.183548 0.034 Uiso 1 1 calc R U . . .
C28 C 0.5903(5) 0.6951(3) 0.2725(2) 0.0254(11) Uani 1 1 d . . . . .
H28 H 0.497656 0.662479 0.270584 0.030 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C1 2.032(4) . ?
Fe1 C5 2.034(4) . ?
Fe1 C11 2.037(4) . ?
Fe1 C10 2.038(4) . ?
Fe1 C14 2.041(4) . ?
Fe1 C2 2.043(4) . ?
Fe1 C4 2.047(4) . ?
Fe1 C12 2.049(4) . ?
Fe1 C13 2.049(4) . ?
Fe1 C3 2.061(4) . ?
N1' C6 1.287(5) . ?
N1' N2' 1.390(4) . ?
O1 C8 1.238(5) . ?
C1 C5 1.424(5) . ?
C1 C2 1.435(5) . ?
C1 C6 1.460(5) . ?
Fe2 C27 2.032(4) . ?
Fe2 C28 2.035(4) . ?
Fe2 C17 2.038(4) . ?
Fe2 C19 2.039(4) . ?
Fe2 C24 2.042(4) . ?
Fe2 C26 2.043(4) . ?
Fe2 C18 2.046(4) . ?
Fe2 C25 2.048(4) . ?
Fe2 C15 2.051(4) . ?
Fe2 C16 2.050(4) . ?
N2' C8 1.351(5) . ?
N2' H2' 0.8800 . ?
O2 C22 1.234(5) . ?
C2 C3 1.420(5) . ?
C2 H2A 1.0000 . ?
C4 C3 1.418(6) . ?
C4 C5 1.434(6) . ?
C4 H4 1.0000 . ?
N4' C22 1.351(5) . ?
N4' N3' 1.394(4) . ?
N4' H4' 0.85(4) . ?
C3 H3 1.0000 . ?
N3' C20 1.286(5) . ?
C5 H5 1.0000 . ?
C6 C7 1.505(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.488(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.417(6) . ?
C10 C14 1.424(6) . ?
C10 H10 1.0000 . ?
C11 C12 1.426(6) . ?
C11 H11 1.0000 . ?
C12 C13 1.417(6) . ?
C12 H12 1.0000 . ?
C13 C14 1.413(6) . ?
C13 H13 1.0000 . ?
C14 H14 1.0000 . ?
C15 C16 1.424(6) . ?
C15 C19 1.441(5) . ?
C15 C20 1.476(5) . ?
C16 C17 1.423(6) . ?
C16 H16 1.0000 . ?
C17 C18 1.429(6) . ?
C17 H17 1.0000 . ?
C18 C19 1.410(6) . ?
C18 H18 1.0000 . ?
C19 H19 1.0000 . ?
C20 C21 1.503(6) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.501(6) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.402(6) . ?
C24 C28 1.419(6) . ?
C24 H24 1.0000 . ?
C25 C26 1.428(7) . ?
C25 H25 1.0000 . ?
C26 C27 1.425(7) . ?
C26 H26 1.0000 . ?
C27 C28 1.414(6) . ?
C27 H27 1.0000 . ?
C28 H28 1.0000 . ?

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
C1 Fe1 C5 41.00(15) . . ?
C1 Fe1 C11 115.40(17) . . ?
C5 Fe1 C11 146.12(17) . . ?
C1 Fe1 C10 107.34(17) . . ?
C5 Fe1 C10 113.20(17) . . ?
C11 Fe1 C10 40.71(18) . . ?
C1 Fe1 C14 130.02(17) . . ?
C5 Fe1 C14 106.43(17) . . ?
C11 Fe1 C14 68.50(17) . . ?
C10 Fe1 C14 40.86(16) . . ?
C1 Fe1 C2 41.25(15) . . ?
C5 Fe1 C2 69.11(16) . . ?
C11 Fe1 C2 110.16(17) . . ?
C10 Fe1 C2 132.10(16) . . ?
C14 Fe1 C2 170.46(16) . . ?
C1 Fe1 C4 68.77(17) . . ?
C5 Fe1 C4 41.14(16) . . ?
C11 Fe1 C4 172.33(19) . . ?
C10 Fe1 C4 145.84(19) . . ?
C14 Fe1 C4 114.34(18) . . ?
C2 Fe1 C4 68.30(16) . . ?
C1 Fe1 C12 148.64(17) . . ?
C5 Fe1 C12 170.23(17) . . ?
C11 Fe1 C12 40.86(17) . . ?
C10 Fe1 C12 68.51(17) . . ?
C14 Fe1 C12 68.17(17) . . ?
C2 Fe1 C12 117.46(16) . . ?
C4 Fe1 C12 132.49(18) . . ?
C1 Fe1 C13 169.14(17) . . ?
C5 Fe1 C13 130.30(17) . . ?
C11 Fe1 C13 68.44(17) . . ?
C10 Fe1 C13 68.43(17) . . ?
C14 Fe1 C13 40.42(16) . . ?
C2 Fe1 C13 148.73(16) . . ?
C4 Fe1 C13 108.71(17) . . ?
C12 Fe1 C13 40.45(17) . . ?
C1 Fe1 C3 68.76(15) . . ?
C5 Fe1 C3 68.86(16) . . ?
C11 Fe1 C3 133.71(18) . . ?
C10 Fe1 C3 171.96(18) . . ?
C14 Fe1 C3 146.98(17) . . ?
C2 Fe1 C3 40.48(14) . . ?
C4 Fe1 C3 40.40(16) . . ?
C12 Fe1 C3 110.88(17) . . ?
C13 Fe1 C3 116.68(16) . . ?
C6 N1' N2' 116.2(3) . . ?
C5 C1 C2 107.9(3) . . ?
C5 C1 C6 127.3(4) . . ?
C2 C1 C6 124.7(4) . . ?
C5 C1 Fe1 69.6(2) . . ?
C2 C1 Fe1 69.8(2) . . ?
C6 C1 Fe1 124.1(3) . . ?
C27 Fe2 C28 40.68(18) . . ?
C27 Fe2 C17 118.46(18) . . ?
C28 Fe2 C17 152.82(18) . . ?
C27 Fe2 C19 125.72(18) . . ?
C28 Fe2 C19 107.25(18) . . ?
C17 Fe2 C19 68.74(17) . . ?
C27 Fe2 C24 68.25(18) . . ?
C28 Fe2 C24 40.75(17) . . ?
C17 Fe2 C24 164.66(18) . . ?
C19 Fe2 C24 119.96(19) . . ?
C27 Fe2 C26 40.95(19) . . ?
C28 Fe2 C26 68.8(2) . . ?
C17 Fe2 C26 107.01(19) . . ?
C19 Fe2 C26 163.40(18) . . ?
C24 Fe2 C26 68.3(2) . . ?
C27 Fe2 C18 106.88(17) . . ?
C28 Fe2 C18 118.49(18) . . ?
C17 Fe2 C18 40.98(16) . . ?
C19 Fe2 C18 40.39(16) . . ?
C24 Fe2 C18 153.53(18) . . ?
C26 Fe2 C18 126.11(19) . . ?
C27 Fe2 C25 68.47(19) . . ?
C28 Fe2 C25 68.32(18) . . ?
C17 Fe2 C25 127.00(18) . . ?
C19 Fe2 C25 154.22(18) . . ?
C24 Fe2 C25 40.09(18) . . ?
C26 Fe2 C25 40.85(19) . . ?
C18 Fe2 C25 164.51(19) . . ?
C27 Fe2 C15 164.34(19) . . ?
C28 Fe2 C15 127.10(19) . . ?
C17 Fe2 C15 68.61(17) . . ?
C19 Fe2 C15 41.27(15) . . ?
C24 Fe2 C15 108.75(18) . . ?
C26 Fe2 C15 153.73(18) . . ?
C18 Fe2 C15 68.54(16) . . ?
C25 Fe2 C15 119.86(18) . . ?
C27 Fe2 C16 153.25(19) . . ?
C28 Fe2 C16 165.02(18) . . ?
C17 Fe2 C16 40.75(16) . . ?
C19 Fe2 C16 68.89(17) . . ?
C24 Fe2 C16 127.56(18) . . ?
C26 Fe2 C16 119.09(19) . . ?
C18 Fe2 C16 68.60(17) . . ?
C25 Fe2 C16 108.47(19) . . ?
C15 Fe2 C16 40.65(16) . . ?
C8 N2' N1' 119.8(4) . . ?
C8 N2' H2' 120.1 . . ?
N1' N2' H2' 120.1 . . ?
C3 C2 C1 108.1(3) . . ?
C3 C2 Fe1 70.4(2) . . ?
C1 C2 Fe1 69.0(2) . . ?
C3 C2 H2A 125.9 . . ?
C1 C2 H2A 125.9 . . ?
Fe1 C2 H2A 125.9 . . ?
C3 C4 C5 108.5(4) . . ?
C3 C4 Fe1 70.3(2) . . ?
C5 C4 Fe1 68.9(2) . . ?
C3 C4 H4 125.7 . . ?
C5 C4 H4 125.7 . . ?
Fe1 C4 H4 125.7 . . ?
C22 N4' N3' 119.1(4) . . ?
C22 N4' H4' 121(3) . . ?
N3' N4' H4' 120(3) . . ?
C4 C3 C2 108.0(4) . . ?
C4 C3 Fe1 69.3(2) . . ?
C2 C3 Fe1 69.1(2) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
Fe1 C3 H3 126.0 . . ?
C20 N3' N4' 116.8(3) . . ?
C1 C5 C4 107.4(4) . . ?
C1 C5 Fe1 69.4(2) . . ?
C4 C5 Fe1 69.9(2) . . ?
C1 C5 H5 126.3 . . ?
C4 C5 H5 126.3 . . ?
Fe1 C5 H5 126.3 . . ?
N1' C6 C1 116.4(4) . . ?
N1' C6 C7 124.4(4) . . ?
C1 C6 C7 119.2(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N2' 119.9(4) . . ?
O1 C8 C9 122.2(4) . . ?
N2' C8 C9 117.9(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C14 107.8(4) . . ?
C11 C10 Fe1 69.6(2) . . ?
C14 C10 Fe1 69.7(2) . . ?
C11 C10 H10 126.1 . . ?
C14 C10 H10 126.1 . . ?
Fe1 C10 H10 126.1 . . ?
C10 C11 C12 108.0(4) . . ?
C10 C11 Fe1 69.7(2) . . ?
C12 C11 Fe1 70.0(2) . . ?
C10 C11 H11 126.0 . . ?
C12 C11 H11 126.0 . . ?
Fe1 C11 H11 126.0 . . ?
C13 C12 C11 107.8(4) . . ?
C13 C12 Fe1 69.8(2) . . ?
C11 C12 Fe1 69.1(2) . . ?
C13 C12 H12 126.1 . . ?
C11 C12 H12 126.1 . . ?
Fe1 C12 H12 126.1 . . ?
C14 C13 C12 108.2(4) . . ?
C14 C13 Fe1 69.5(2) . . ?
C12 C13 Fe1 69.8(2) . . ?
C14 C13 H13 125.9 . . ?
C12 C13 H13 125.9 . . ?
Fe1 C13 H13 125.9 . . ?
C13 C14 C10 108.2(4) . . ?
C13 C14 Fe1 70.1(2) . . ?
C10 C14 Fe1 69.4(2) . . ?
C13 C14 H14 125.9 . . ?
C10 C14 H14 125.9 . . ?
Fe1 C14 H14 125.9 . . ?
C16 C15 C19 107.6(3) . . ?
C16 C15 C20 126.1(4) . . ?
C19 C15 C20 126.2(4) . . ?
C16 C15 Fe2 69.7(2) . . ?
C19 C15 Fe2 68.9(2) . . ?
C20 C15 Fe2 128.8(3) . . ?
C17 C16 C15 108.0(4) . . ?
C17 C16 Fe2 69.2(2) . . ?
C15 C16 Fe2 69.7(2) . . ?
C17 C16 H16 126.0 . . ?
C15 C16 H16 126.0 . . ?
Fe2 C16 H16 126.0 . . ?
C16 C17 C18 108.0(4) . . ?
C16 C17 Fe2 70.1(2) . . ?
C18 C17 Fe2 69.8(2) . . ?
C16 C17 H17 126.0 . . ?
C18 C17 H17 126.0 . . ?
Fe2 C17 H17 126.0 . . ?
C19 C18 C17 108.3(4) . . ?
C19 C18 Fe2 69.6(2) . . ?
C17 C18 Fe2 69.2(2) . . ?
C19 C18 H18 125.8 . . ?
C17 C18 H18 125.8 . . ?
Fe2 C18 H18 125.8 . . ?
C18 C19 C15 108.0(4) . . ?
C18 C19 Fe2 70.1(2) . . ?
C15 C19 Fe2 69.8(2) . . ?
C18 C19 H19 126.0 . . ?
C15 C19 H19 126.0 . . ?
Fe2 C19 H19 126.0 . . ?
N3' C20 C15 115.1(4) . . ?
N3' C20 C21 125.5(4) . . ?
C15 C20 C21 119.3(4) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O2 C22 N4' 119.7(4) . . ?
O2 C22 C23 121.8(4) . . ?
N4' C22 C23 118.4(4) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C28 108.7(4) . . ?
C25 C24 Fe2 70.2(2) . . ?
C28 C24 Fe2 69.4(2) . . ?
C25 C24 H24 125.6 . . ?
C28 C24 H24 125.6 . . ?
Fe2 C24 H24 125.6 . . ?
C24 C25 C26 108.2(4) . . ?
C24 C25 Fe2 69.7(2) . . ?
C26 C25 Fe2 69.4(3) . . ?
C24 C25 H25 125.9 . . ?
C26 C25 H25 125.9 . . ?
Fe2 C25 H25 125.9 . . ?
C25 C26 C27 107.1(4) . . ?
C25 C26 Fe2 69.8(3) . . ?
C27 C26 Fe2 69.1(3) . . ?
C25 C26 H26 126.4 . . ?
C27 C26 H26 126.4 . . ?
Fe2 C26 H26 126.4 . . ?
C28 C27 C26 108.4(4) . . ?
C28 C27 Fe2 69.8(2) . . ?
C26 C27 Fe2 69.9(2) . . ?
C28 C27 H27 125.8 . . ?
C26 C27 H27 125.8 . . ?
Fe2 C27 H27 125.8 . . ?
C27 C28 C24 107.6(4) . . ?
C27 C28 Fe2 69.6(2) . . ?
C24 C28 Fe2 69.9(2) . . ?
C27 C28 H28 126.2 . . ?
C24 C28 H28 126.2 . . ?
Fe2 C28 H28 126.2 . . ?

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
N2' H2' O2 0.88 2.12 2.977(5) 163.8 . yes
N4' H4' O1 0.85(4) 2.20(4) 3.015(5) 162(4) . yes

_refine_diff_density_max         0.316
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_me181127Fe1
_database_code_depnum_ccdc_archive 'CCDC 2053762'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Fe1 N2 O1'
_chemical_formula_weight         284.14

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'
Fe Fe 0.3463 0.8444 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.3414(11)
_cell_length_b                   7.8369(5)
_cell_length_c                   19.8330(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2539.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    23544
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.501
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.176
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5300
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector
scaling and absorption correction
;
_exptl_absorpt_special_details   
;
The ratio of minimum to maximum
apparent transmission was 0.703
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            20629
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_av_R_equivalents  0.1419
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.402
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2766
_reflns_number_gt                1879
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0366P)²+2.2729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2766
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.39869(3) 0.38264(6) 0.34706(2) 0.01859(14) Uani 1 1 d . . . . .
N1 N 0.28722(15) 0.3103(3) 0.52622(11) 0.0175(6) Uani 1 1 d . . . . .
O1 O 0.16240(13) 0.3642(3) 0.61235(11) 0.0268(5) Uani 1 1 d . . . . .
C1 C 0.38200(18) 0.4134(4) 0.44830(13) 0.0176(7) Uani 1 1 d . . . . .
C2 C 0.46525(19) 0.4496(4) 0.42886(14) 0.0213(7) Uani 1 1 d . . . . .
H2 H 0.515439 0.390707 0.445895 0.026 Uiso 1 1 calc R U . . .
N2 N 0.26066(15) 0.1875(3) 0.57171(11) 0.0183(6) Uani 1 1 d . . . . .
H2A H 0.285183 0.087716 0.574347 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4629(2) 0.5867(4) 0.38205(14) 0.0248(8) Uani 1 1 d . . . . .
H3 H 0.511503 0.639406 0.359577 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3807(2) 0.6346(4) 0.37177(16) 0.0291(8) Uani 1 1 d . . . . .
H4 H 0.361050 0.726018 0.340539 0.035 Uiso 1 1 calc R U . . .
C5 C 0.3302(2) 0.5278(4) 0.41280(15) 0.0250(8) Uani 1 1 d . . . . .
H5 H 0.269060 0.531287 0.415258 0.030 Uiso 1 1 calc R U . . .
C6 C 0.35583(19) 0.2806(4) 0.49636(14) 0.0185(7) Uani 1 1 d . . . . .
C8 C 0.16925(19) 0.0814(4) 0.65694(15) 0.0255(7) Uani 1 1 d . . . . .
H8A H 0.124177 0.120616 0.685616 0.038 Uiso 1 1 calc R U . . .
H8B H 0.215164 0.045095 0.685305 0.038 Uiso 1 1 calc R U . . .
H8C H 0.150729 -0.014886 0.629354 0.038 Uiso 1 1 calc R U . . .
C7 C 0.19638(19) 0.2247(4) 0.61174(14) 0.0199(7) Uani 1 1 d . . . . .
C9 C 0.4098(2) 0.1282(4) 0.50788(16) 0.0317(8) Uani 1 1 d . . . . .
H9A H 0.458730 0.137395 0.479532 0.048 Uiso 1 1 calc R U . . .
H9B H 0.379844 0.024004 0.496222 0.048 Uiso 1 1 calc R U . . .
H9C H 0.426073 0.123843 0.555414 0.048 Uiso 1 1 calc R U . . .
C10 C 0.3750(3) 0.1333(5) 0.32499(18) 0.0403(10) Uani 1 1 d . . . . .
H10 H 0.355476 0.044473 0.357426 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4578(2) 0.1739(4) 0.31064(16) 0.0332(9) Uani 1 1 d . . . . .
H11 H 0.506976 0.118380 0.331156 0.040 Uiso 1 1 calc R U . . .
C12 C 0.4587(2) 0.3062(4) 0.26206(14) 0.0284(8) Uani 1 1 d . . . . .
H12 H 0.508667 0.361001 0.242569 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3766(2) 0.3484(5) 0.24605(16) 0.0348(9) Uani 1 1 d . . . . .
H13 H 0.358203 0.437844 0.213430 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3251(2) 0.2406(5) 0.28533(17) 0.0424(10) Uani 1 1 d . . . . .
H14 H 0.263924 0.241754 0.285234 0.051 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C2 2.022(3) . ?
Fe1 C11 2.033(3) . ?
Fe1 C3 2.035(3) . ?
Fe1 C10 2.040(4) . ?
Fe1 C1 2.041(3) . ?
Fe1 C12 2.040(3) . ?
Fe1 C14 2.045(3) . ?
Fe1 C13 2.053(3) . ?
Fe1 C4 2.056(3) . ?
Fe1 C5 2.061(3) . ?
N1 C6 1.289(4) . ?
N1 N2 1.389(3) . ?
O1 C7 1.226(4) . ?
C1 C5 1.421(4) . ?
C1 C2 1.442(4) . ?
C1 C6 1.474(4) . ?
C2 C3 1.420(4) . ?
C2 H2 1.0000 . ?
N2 C7 1.349(4) . ?
N2 H2A 0.8800 . ?
C3 C4 1.410(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.430(4) . ?
C4 H4 1.0000 . ?
C5 H5 1.0000 . ?
C6 C9 1.502(4) . ?
C8 C7 1.504(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C14 1.411(5) . ?
C10 C11 1.419(5) . ?
C10 H10 1.0000 . ?
C11 C12 1.416(5) . ?
C11 H11 1.0000 . ?
C12 C13 1.418(5) . ?
C12 H12 1.0000 . ?
C13 C14 1.424(5) . ?
C13 H13 1.0000 . ?
C14 H14 1.0000 . ?

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 C11 103.79(14) . . ?
C2 Fe1 C3 40.98(12) . . ?
C11 Fe1 C3 120.57(15) . . ?
C2 Fe1 C10 121.53(15) . . ?
C11 Fe1 C10 40.78(15) . . ?
C3 Fe1 C10 157.53(16) . . ?
C2 Fe1 C1 41.58(11) . . ?
C11 Fe1 C1 120.54(13) . . ?
C3 Fe1 C1 68.94(12) . . ?
C10 Fe1 C1 107.39(13) . . ?
C2 Fe1 C12 118.71(13) . . ?
C11 Fe1 C12 40.68(13) . . ?
C3 Fe1 C12 105.34(13) . . ?
C10 Fe1 C12 68.45(14) . . ?
C1 Fe1 C12 155.77(13) . . ?
C2 Fe1 C14 159.64(15) . . ?
C11 Fe1 C14 68.20(16) . . ?
C3 Fe1 C14 159.23(15) . . ?
C10 Fe1 C14 40.41(16) . . ?
C1 Fe1 C14 125.07(13) . . ?
C12 Fe1 C14 68.18(14) . . ?
C2 Fe1 C13 155.67(13) . . ?
C11 Fe1 C13 68.39(14) . . ?
C3 Fe1 C13 121.75(14) . . ?
C10 Fe1 C13 68.41(15) . . ?
C1 Fe1 C13 162.17(13) . . ?
C12 Fe1 C13 40.54(13) . . ?
C14 Fe1 C13 40.66(14) . . ?
C2 Fe1 C4 68.68(13) . . ?
C11 Fe1 C4 157.80(14) . . ?
C3 Fe1 C4 40.32(13) . . ?
C10 Fe1 C4 160.79(15) . . ?
C1 Fe1 C4 68.47(12) . . ?
C12 Fe1 C4 123.21(13) . . ?
C14 Fe1 C4 125.55(16) . . ?
C13 Fe1 C4 109.45(15) . . ?
C2 Fe1 C5 69.00(13) . . ?
C11 Fe1 C5 158.02(13) . . ?
C3 Fe1 C5 68.33(13) . . ?
C10 Fe1 C5 124.16(14) . . ?
C1 Fe1 C5 40.52(11) . . ?
C12 Fe1 C5 161.06(13) . . ?
C14 Fe1 C5 111.07(15) . . ?
C13 Fe1 C5 126.42(14) . . ?
C4 Fe1 C5 40.65(12) . . ?
C6 N1 N2 116.4(2) . . ?
C5 C1 C2 107.8(3) . . ?
C5 C1 C6 126.4(3) . . ?
C2 C1 C6 125.8(3) . . ?
C5 C1 Fe1 70.51(16) . . ?
C2 C1 Fe1 68.53(15) . . ?
C6 C1 Fe1 126.3(2) . . ?
C3 C2 C1 107.4(3) . . ?
C3 C2 Fe1 69.97(18) . . ?
C1 C2 Fe1 69.88(16) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
Fe1 C2 H2 126.3 . . ?
C7 N2 N1 118.4(3) . . ?
C7 N2 H2A 120.8 . . ?
N1 N2 H2A 120.8 . . ?
C4 C3 C2 108.8(3) . . ?
C4 C3 Fe1 70.6(2) . . ?
C2 C3 Fe1 69.05(18) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
Fe1 C3 H3 125.6 . . ?
C3 C4 C5 108.2(3) . . ?
C3 C4 Fe1 69.04(19) . . ?
C5 C4 Fe1 69.88(18) . . ?
C3 C4 H4 125.9 . . ?
C5 C4 H4 125.9 . . ?
Fe1 C4 H4 125.9 . . ?
C1 C5 C4 107.9(3) . . ?
C1 C5 Fe1 68.97(17) . . ?
C4 C5 Fe1 69.47(18) . . ?
C1 C5 H5 126.0 . . ?
C4 C5 H5 126.0 . . ?
Fe1 C5 H5 126.0 . . ?
N1 C6 C1 115.0(3) . . ?
N1 C6 C9 125.7(3) . . ?
C1 C6 C9 119.3(3) . . ?
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 . . ?
O1 C7 N2 123.5(3) . . ?
O1 C7 C8 121.8(3) . . ?
N2 C7 C8 114.8(3) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C14 C10 C11 107.8(3) . . ?
C14 C10 Fe1 70.0(2) . . ?
C11 C10 Fe1 69.3(2) . . ?
C14 C10 H10 126.1 . . ?
C11 C10 H10 126.1 . . ?
Fe1 C10 H10 126.1 . . ?
C12 C11 C10 108.1(4) . . ?
C12 C11 Fe1 69.94(19) . . ?
C10 C11 Fe1 69.9(2) . . ?
C12 C11 H11 126.0 . . ?
C10 C11 H11 126.0 . . ?
Fe1 C11 H11 126.0 . . ?
C11 C12 C13 108.3(3) . . ?
C11 C12 Fe1 69.38(18) . . ?
C13 C12 Fe1 70.23(18) . . ?
C11 C12 H12 125.9 . . ?
C13 C12 H12 125.9 . . ?
Fe1 C12 H12 125.9 . . ?
C12 C13 C14 107.3(3) . . ?
C12 C13 Fe1 69.23(17) . . ?
C14 C13 Fe1 69.36(18) . . ?
C12 C13 H13 126.3 . . ?
C14 C13 H13 126.3 . . ?
Fe1 C13 H13 126.3 . . ?
C10 C14 C13 108.5(3) . . ?
C10 C14 Fe1 69.6(2) . . ?
C13 C14 Fe1 69.97(19) . . ?
C10 C14 H14 125.7 . . ?
C13 C14 H14 125.7 . . ?
Fe1 C14 H14 125.7 . . ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_me161101fe1
_database_code_depnum_ccdc_archive 'CCDC 2053763'
loop_
_audit_author_name
_audit_author_address
'Ales Ruzicka'
;University of Pardubice
Czech Republic
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2021-08-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 Fe N2'
_chemical_formula_weight         242.10

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'
Fe Fe 0.3463 0.8444 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

_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, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   28.021(2)
_cell_length_b                   7.3169(5)
_cell_length_c                   10.7673(8)
_cell_angle_alpha                90
_cell_angle_beta                 101.809(2)
_cell_angle_gamma                90
_cell_volume                     2160.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    32050
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       bar
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.361
_shelx_estimated_absorpt_T_min   0.692
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 - Venture'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            32050
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.667
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4817
_reflns_number_gt                4458
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_max     0.949
_reflns_Friedel_fraction_full    0.973

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.3'
_computing_cell_refinement       'APEX3 v2016.9-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component twin. There are two unacceptably large residual peaks of magnitude 2.5. 
These are in chemically impossible positions and we have no explaination for these.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+20.5090P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1818 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.052(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4817
_refine_ls_number_parameters     286
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1366
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_restrained_S_all      1.182
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.34295(3) 0.72306(18) 0.16339(8) 0.0122(2) Uani 1 1 d . . . . .
N1 N 0.4671(2) 0.5171(11) 0.1048(7) 0.0187(14) Uani 1 1 d . . . . .
C1 C 0.3843(3) 0.5188(11) 0.1103(7) 0.0137(14) Uani 1 1 d . . . . .
Fe2 Fe 0.34011(3) 1.22507(17) 0.68115(8) 0.0122(2) Uani 1 1 d . . . . .
N2 N 0.5164(3) 0.4805(12) 0.1634(7) 0.0234(16) Uani 1 1 d . . . . .
H2A H 0.525(4) 0.381(16) 0.215(11) 0.028 Uiso 1 1 d . U . . .
H2B H 0.541(4) 0.526(15) 0.095(10) 0.028 Uiso 1 1 d . U . . .
C2 C 0.3690(3) 0.6418(12) 0.0080(7) 0.0179(16) Uani 1 1 d . . . . .
H2 H 0.391065 0.714693 -0.035275 0.021 Uiso 1 1 calc R U . . .
C3 C 0.3166(3) 0.6463(12) -0.0217(8) 0.0208(17) Uani 1 1 d . . . . .
H3 H 0.295676 0.721661 -0.089089 0.025 Uiso 1 1 calc R U . . .
N3 N 0.4668(2) 1.0179(10) 0.8616(6) 0.0156(13) Uani 1 1 d . . . . .
C5 C 0.3408(3) 0.4461(11) 0.1465(8) 0.0197(17) Uani 1 1 d . . . . .
H5 H 0.339917 0.356260 0.215998 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3000(3) 0.5236(12) 0.0636(8) 0.0179(16) Uani 1 1 d . . . . .
H4 H 0.265118 0.499950 0.066623 0.022 Uiso 1 1 calc R U . . .
N4 N 0.5151(3) 0.9796(12) 0.8524(8) 0.0247(16) Uani 1 1 d . . . . .
H4A H 0.519(4) 0.863(16) 0.821(11) 0.030 Uiso 1 1 d . U . . .
H4B H 0.532(4) 0.974(15) 0.942(11) 0.030 Uiso 1 1 d . U . . .
C9 C 0.3692(3) 0.9817(11) 0.2083(8) 0.0193(16) Uani 1 1 d . . . . .
H9 H 0.389225 1.056271 0.160188 0.023 Uiso 1 1 calc R U . . .
C8 C 0.3870(3) 0.8592(12) 0.3085(8) 0.0223(18) Uani 1 1 d . . . . .
H8 H 0.422163 0.831277 0.342985 0.027 Uiso 1 1 calc R U . . .
C7 C 0.4471(3) 0.3883(14) 0.3004(8) 0.0263(19) Uani 1 1 d . . . . .
H7A H 0.417978 0.387050 0.337516 0.039 Uiso 1 1 calc R U . . .
H7B H 0.472931 0.458530 0.355173 0.039 Uiso 1 1 calc R U . . .
H7C H 0.458312 0.262638 0.292768 0.039 Uiso 1 1 calc R U . . .
C6 C 0.4351(3) 0.4752(11) 0.1709(7) 0.0166(15) Uani 1 1 d . . . . .
C10 C 0.3172(3) 0.9795(12) 0.1887(9) 0.0254(19) Uani 1 1 d . . . . .
H10 H 0.294441 1.051878 0.123195 0.030 Uiso 1 1 calc R U . . .
C11 C 0.3033(3) 0.8571(12) 0.2759(9) 0.025(2) Uani 1 1 d . . . . .
H11 H 0.269094 0.827962 0.283023 0.030 Uiso 1 1 calc R U . . .
C12 C 0.3467(3) 0.7796(11) 0.3517(8) 0.0229(18) Uani 1 1 d . . . . .
H12 H 0.348488 0.688569 0.421747 0.027 Uiso 1 1 calc R U . . .
C13 C 0.3829(3) 1.0206(11) 0.7748(7) 0.0147(15) Uani 1 1 d . . . . .
C14 C 0.3386(3) 0.9484(11) 0.7003(7) 0.0141(15) Uani 1 1 d . . . . .
H14 H 0.336060 0.857255 0.630065 0.017 Uiso 1 1 calc R U . . .
C15 C 0.2989(3) 1.0292(12) 0.7432(8) 0.0213(17) Uani 1 1 d . . . . .
H15 H 0.263560 1.004928 0.708330 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3182(3) 1.1534(12) 0.8452(8) 0.0183(16) Uani 1 1 d . . . . .
H16 H 0.298703 1.230720 0.893225 0.022 Uiso 1 1 calc R U . . .
C17 C 0.3695(3) 1.1470(11) 0.8643(7) 0.0155(15) Uani 1 1 d . . . . .
H17 H 0.392653 1.220931 0.927753 0.019 Uiso 1 1 calc R U . . .
C18 C 0.4331(3) 0.9764(10) 0.7650(7) 0.0145(14) Uani 1 1 d . . . . .
C19 C 0.4429(3) 0.8903(13) 0.6465(8) 0.0236(18) Uani 1 1 d . . . . .
H19A H 0.413581 0.897705 0.579257 0.035 Uiso 1 1 calc R U . . .
H19B H 0.451931 0.761846 0.663114 0.035 Uiso 1 1 calc R U . . .
H19C H 0.469737 0.955022 0.619675 0.035 Uiso 1 1 calc R U . . .
C20 C 0.3813(3) 1.3575(12) 0.5737(8) 0.0221(18) Uani 1 1 d . . . . .
H20 H 0.416105 1.330444 0.571713 0.027 Uiso 1 1 calc R U . . .
C21 C 0.3397(4) 1.2762(12) 0.4946(8) 0.026(2) Uani 1 1 d . . . . .
H21 H 0.340184 1.182436 0.427271 0.031 Uiso 1 1 calc R U . . .
C22 C 0.2974(4) 1.3517(13) 0.5290(8) 0.026(2) Uani 1 1 d . . . . .
H22 H 0.262805 1.320269 0.490274 0.031 Uiso 1 1 calc R U . . .
C23 C 0.3129(3) 1.4791(12) 0.6270(8) 0.0231(18) Uani 1 1 d . . . . .
H23 H 0.291086 1.552711 0.670510 0.028 Uiso 1 1 calc R U . . .
C24 C 0.3649(3) 1.4829(11) 0.6557(7) 0.0203(17) Uani 1 1 d . . . . .
H24 H 0.385854 1.560137 0.721719 0.024 Uiso 1 1 calc R U . . .


_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C5 2.034(8) . ?
Fe1 C8 2.042(8) . ?
Fe1 C1 2.043(7) . ?
Fe1 C2 2.046(8) . ?
Fe1 C10 2.048(9) . ?
Fe1 C12 2.050(8) . ?
Fe1 C4 2.050(8) . ?
Fe1 C9 2.052(8) . ?
Fe1 C11 2.053(9) . ?
Fe1 C3 2.056(8) . ?
N1 C6 1.292(10) . ?
N1 N2 1.421(10) . ?
C1 C2 1.419(11) . ?
C1 C5 1.452(11) . ?
C1 C6 1.475(11) . ?
Fe2 C14 2.036(8) . ?
Fe2 C15 2.038(8) . ?
Fe2 C20 2.038(8) . ?
Fe2 C21 2.041(8) . ?
Fe2 C22 2.043(8) . ?
Fe2 C24 2.048(8) . ?
Fe2 C23 2.048(9) . ?
Fe2 C13 2.049(8) . ?
Fe2 C16 2.054(8) . ?
Fe2 C17 2.056(7) . ?
N2 H2A 0.92(12) . ?
N2 H2B 1.16(10) . ?
C2 C3 1.439(12) . ?
C2 H2 1.0000 . ?
C3 C4 1.428(12) . ?
C3 H3 1.0000 . ?
N3 C18 1.290(10) . ?
N3 N4 1.405(10) . ?
C5 C4 1.418(12) . ?
C5 H5 1.0000 . ?
C4 H4 1.0000 . ?
N4 H4A 0.93(12) . ?
N4 H4B 0.98(11) . ?
C9 C8 1.414(12) . ?
C9 C10 1.428(12) . ?
C9 H9 1.0000 . ?
C8 C12 1.429(12) . ?
C8 H8 1.0000 . ?
C7 C6 1.507(11) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 C11 1.410(14) . ?
C10 H10 1.0000 . ?
C11 C12 1.436(13) . ?
C11 H11 1.0000 . ?
C12 H12 1.0000 . ?
C13 C14 1.436(11) . ?
C13 C17 1.440(11) . ?
C13 C18 1.467(11) . ?
C14 C15 1.417(12) . ?
C14 H14 1.0000 . ?
C15 C16 1.443(12) . ?
C15 H15 1.0000 . ?
C16 C17 1.411(12) . ?
C16 H16 1.0000 . ?
C17 H17 1.0000 . ?
C18 C19 1.498(11) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C24 1.414(12) . ?
C20 C21 1.425(13) . ?
C20 H20 1.0000 . ?
C21 C22 1.425(14) . ?
C21 H21 1.0000 . ?
C22 C23 1.408(13) . ?
C22 H22 1.0000 . ?
C23 C24 1.426(13) . ?
C23 H23 1.0000 . ?
C24 H24 1.0000 . ?

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
C5 Fe1 C8 123.8(4) . . ?
C5 Fe1 C1 41.7(3) . . ?
C8 Fe1 C1 106.4(3) . . ?
C5 Fe1 C2 69.3(4) . . ?
C8 Fe1 C2 120.4(4) . . ?
C1 Fe1 C2 40.6(3) . . ?
C5 Fe1 C10 156.9(4) . . ?
C8 Fe1 C10 68.0(4) . . ?
C1 Fe1 C10 160.5(4) . . ?
C2 Fe1 C10 124.7(4) . . ?
C5 Fe1 C12 106.5(4) . . ?
C8 Fe1 C12 40.9(3) . . ?
C1 Fe1 C12 120.4(3) . . ?
C2 Fe1 C12 155.8(4) . . ?
C10 Fe1 C12 68.4(4) . . ?
C5 Fe1 C4 40.6(3) . . ?
C8 Fe1 C4 161.2(4) . . ?
C1 Fe1 C4 68.8(3) . . ?
C2 Fe1 C4 68.5(3) . . ?
C10 Fe1 C4 122.5(4) . . ?
C12 Fe1 C4 124.6(3) . . ?
C5 Fe1 C9 160.4(4) . . ?
C8 Fe1 C9 40.4(3) . . ?
C1 Fe1 C9 123.0(3) . . ?
C2 Fe1 C9 106.8(3) . . ?
C10 Fe1 C9 40.8(3) . . ?
C12 Fe1 C9 68.8(3) . . ?
C4 Fe1 C9 157.5(3) . . ?
C5 Fe1 C11 121.3(4) . . ?
C8 Fe1 C11 68.3(4) . . ?
C1 Fe1 C11 157.1(4) . . ?
C2 Fe1 C11 161.5(4) . . ?
C10 Fe1 C11 40.2(4) . . ?
C12 Fe1 C11 41.0(4) . . ?
C4 Fe1 C11 108.6(3) . . ?
C9 Fe1 C11 68.4(3) . . ?
C5 Fe1 C3 69.1(4) . . ?
C8 Fe1 C3 156.3(4) . . ?
C1 Fe1 C3 68.9(3) . . ?
C2 Fe1 C3 41.1(3) . . ?
C10 Fe1 C3 108.2(4) . . ?
C12 Fe1 C3 161.6(4) . . ?
C4 Fe1 C3 40.7(3) . . ?
C9 Fe1 C3 121.4(4) . . ?
C11 Fe1 C3 124.9(4) . . ?
C6 N1 N2 115.6(7) . . ?
C2 C1 C5 107.8(7) . . ?
C2 C1 C6 126.2(7) . . ?
C5 C1 C6 126.0(7) . . ?
C2 C1 Fe1 69.8(4) . . ?
C5 C1 Fe1 68.8(4) . . ?
C6 C1 Fe1 125.8(5) . . ?
C14 Fe2 C15 40.7(3) . . ?
C14 Fe2 C20 123.8(3) . . ?
C15 Fe2 C20 161.0(4) . . ?
C14 Fe2 C21 106.6(3) . . ?
C15 Fe2 C21 124.2(4) . . ?
C20 Fe2 C21 40.9(4) . . ?
C14 Fe2 C22 120.7(4) . . ?
C15 Fe2 C22 107.7(4) . . ?
C20 Fe2 C22 68.7(4) . . ?
C21 Fe2 C22 40.9(4) . . ?
C14 Fe2 C24 160.8(4) . . ?
C15 Fe2 C24 157.3(4) . . ?
C20 Fe2 C24 40.5(3) . . ?
C21 Fe2 C24 68.5(3) . . ?
C22 Fe2 C24 68.5(3) . . ?
C14 Fe2 C23 156.4(4) . . ?
C15 Fe2 C23 121.9(3) . . ?
C20 Fe2 C23 68.2(4) . . ?
C21 Fe2 C23 68.1(4) . . ?
C22 Fe2 C23 40.3(4) . . ?
C24 Fe2 C23 40.7(4) . . ?
C14 Fe2 C13 41.1(3) . . ?
C15 Fe2 C13 68.9(3) . . ?
C20 Fe2 C13 106.5(3) . . ?
C21 Fe2 C13 120.2(3) . . ?
C22 Fe2 C13 156.0(4) . . ?
C24 Fe2 C13 123.9(3) . . ?
C23 Fe2 C13 161.6(4) . . ?
C14 Fe2 C16 69.1(3) . . ?
C15 Fe2 C16 41.3(3) . . ?
C20 Fe2 C16 156.0(4) . . ?
C21 Fe2 C16 162.0(4) . . ?
C22 Fe2 C16 125.2(4) . . ?
C24 Fe2 C16 121.3(3) . . ?
C23 Fe2 C16 108.5(3) . . ?
C13 Fe2 C16 68.8(3) . . ?
C14 Fe2 C17 68.9(3) . . ?
C15 Fe2 C17 68.4(3) . . ?
C20 Fe2 C17 121.0(4) . . ?
C21 Fe2 C17 156.2(4) . . ?
C22 Fe2 C17 161.6(4) . . ?
C24 Fe2 C17 107.7(3) . . ?
C23 Fe2 C17 125.3(4) . . ?
C13 Fe2 C17 41.1(3) . . ?
C16 Fe2 C17 40.1(3) . . ?
N1 N2 H2A 122(7) . . ?
N1 N2 H2B 108(5) . . ?
H2A N2 H2B 119(9) . . ?
C1 C2 C3 108.5(7) . . ?
C1 C2 Fe1 69.5(4) . . ?
C3 C2 Fe1 69.8(4) . . ?
C1 C2 H2 125.7 . . ?
C3 C2 H2 125.7 . . ?
Fe1 C2 H2 125.7 . . ?
C4 C3 C2 107.1(7) . . ?
C4 C3 Fe1 69.4(5) . . ?
C2 C3 Fe1 69.1(4) . . ?
C4 C3 H3 126.4 . . ?
C2 C3 H3 126.4 . . ?
Fe1 C3 H3 126.4 . . ?
C18 N3 N4 116.9(7) . . ?
C4 C5 C1 107.3(7) . . ?
C4 C5 Fe1 70.3(5) . . ?
C1 C5 Fe1 69.4(4) . . ?
C4 C5 H5 126.4 . . ?
C1 C5 H5 126.4 . . ?
Fe1 C5 H5 126.4 . . ?
C5 C4 C3 109.3(7) . . ?
C5 C4 Fe1 69.1(5) . . ?
C3 C4 Fe1 69.9(5) . . ?
C5 C4 H4 125.4 . . ?
C3 C4 H4 125.4 . . ?
Fe1 C4 H4 125.4 . . ?
N3 N4 H4A 113(7) . . ?
N3 N4 H4B 103(6) . . ?
H4A N4 H4B 104(9) . . ?
C8 C9 C10 107.2(7) . . ?
C8 C9 Fe1 69.4(5) . . ?
C10 C9 Fe1 69.5(5) . . ?
C8 C9 H9 126.4 . . ?
C10 C9 H9 126.4 . . ?
Fe1 C9 H9 126.4 . . ?
C9 C8 C12 109.1(8) . . ?
C9 C8 Fe1 70.2(5) . . ?
C12 C8 Fe1 69.9(5) . . ?
C9 C8 H8 125.4 . . ?
C12 C8 H8 125.4 . . ?
Fe1 C8 H8 125.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C6 C1 115.0(7) . . ?
N1 C6 C7 124.1(8) . . ?
C1 C6 C7 120.9(7) . . ?
C11 C10 C9 108.7(8) . . ?
C11 C10 Fe1 70.1(5) . . ?
C9 C10 Fe1 69.7(5) . . ?
C11 C10 H10 125.6 . . ?
C9 C10 H10 125.6 . . ?
Fe1 C10 H10 125.6 . . ?
C10 C11 C12 108.2(8) . . ?
C10 C11 Fe1 69.7(5) . . ?
C12 C11 Fe1 69.4(5) . . ?
C10 C11 H11 125.9 . . ?
C12 C11 H11 125.9 . . ?
Fe1 C11 H11 125.9 . . ?
C8 C12 C11 106.8(8) . . ?
C8 C12 Fe1 69.2(5) . . ?
C11 C12 Fe1 69.6(5) . . ?
C8 C12 H12 126.6 . . ?
C11 C12 H12 126.6 . . ?
Fe1 C12 H12 126.6 . . ?
C14 C13 C17 107.1(7) . . ?
C14 C13 C18 127.7(7) . . ?
C17 C13 C18 125.1(7) . . ?
C14 C13 Fe2 68.9(4) . . ?
C17 C13 Fe2 69.7(4) . . ?
C18 C13 Fe2 126.8(5) . . ?
C15 C14 C13 108.2(7) . . ?
C15 C14 Fe2 69.7(5) . . ?
C13 C14 Fe2 69.9(4) . . ?
C15 C14 H14 125.9 . . ?
C13 C14 H14 125.9 . . ?
Fe2 C14 H14 125.9 . . ?
C14 C15 C16 108.3(7) . . ?
C14 C15 Fe2 69.6(4) . . ?
C16 C15 Fe2 70.0(5) . . ?
C14 C15 H15 125.8 . . ?
C16 C15 H15 125.8 . . ?
Fe2 C15 H15 125.8 . . ?
C17 C16 C15 107.6(7) . . ?
C17 C16 Fe2 70.0(4) . . ?
C15 C16 Fe2 68.7(4) . . ?
C17 C16 H16 126.2 . . ?
C15 C16 H16 126.2 . . ?
Fe2 C16 H16 126.2 . . ?
C16 C17 C13 108.8(7) . . ?
C16 C17 Fe2 69.9(4) . . ?
C13 C17 Fe2 69.2(4) . . ?
C16 C17 H17 125.6 . . ?
C13 C17 H17 125.6 . . ?
Fe2 C17 H17 125.6 . . ?
N3 C18 C13 116.4(7) . . ?
N3 C18 C19 123.6(7) . . ?
C13 C18 C19 120.0(7) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C24 C20 C21 108.3(8) . . ?
C24 C20 Fe2 70.1(5) . . ?
C21 C20 Fe2 69.6(5) . . ?
C24 C20 H20 125.9 . . ?
C21 C20 H20 125.9 . . ?
Fe2 C20 H20 125.9 . . ?
C20 C21 C22 107.7(8) . . ?
C20 C21 Fe2 69.5(5) . . ?
C22 C21 Fe2 69.6(5) . . ?
C20 C21 H21 126.1 . . ?
C22 C21 H21 126.1 . . ?
Fe2 C21 H21 126.1 . . ?
C23 C22 C21 107.8(8) . . ?
C23 C22 Fe2 70.1(5) . . ?
C21 C22 Fe2 69.5(5) . . ?
C23 C22 H22 126.1 . . ?
C21 C22 H22 126.1 . . ?
Fe2 C22 H22 126.1 . . ?
C22 C23 C24 108.7(8) . . ?
C22 C23 Fe2 69.7(5) . . ?
C24 C23 Fe2 69.6(5) . . ?
C22 C23 H23 125.7 . . ?
C24 C23 H23 125.7 . . ?
Fe2 C23 H23 125.7 . . ?
C20 C24 C23 107.5(8) . . ?
C20 C24 Fe2 69.4(5) . . ?
C23 C24 Fe2 69.6(5) . . ?
C20 C24 H24 126.2 . . ?
C23 C24 H24 126.2 . . ?
Fe2 C24 H24 126.2 . . ?

_refine_diff_density_max         2.371
_refine_diff_density_min         -1.573
_refine_diff_density_rms         0.137

