# 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 2022

####################################################################### 
# 
# 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. 
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data_test2
_database_code_depnum_ccdc_archive 'CCDC 2129661'
loop_
_audit_author_name
_audit_author_address
'Mauricio Fuentealba'
;Pontificia Universidad Catolica de Valparaiso
Chile
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;
_audit_creation_date             2017-06-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 Fe N2 O'
_chemical_formula_sum            'C20 H26 Fe N2 O'
_chemical_formula_weight         366.28
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.5430(4)
_cell_length_b                   8.7848(5)
_cell_length_c                   27.6566(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1832.63(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7341
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.850
_exptl_absorpt_coefficient_mu    0.831
_exptl_absorpt_correction_T_max  0.9366
_exptl_absorpt_correction_T_min  0.8484
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0636 before and 0.0596 after correction. The Ratio of minimum to maximum transmission is 0.9058. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.137
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            25642
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.404
_diffrn_reflns_theta_min         2.433
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3024
_reflns_number_total             3758
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1065 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3758
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+0.3850P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0768
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8),
 C9(H9), C12(H12)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.60247(6) 0.49307(6) 0.44195(2) 0.03975(14) Uani 1 1 d . . . . .
O1 O 0.9042(4) 0.5116(3) 0.33150(8) 0.0634(7) Uani 1 1 d . . . . .
N1 N 0.8246(5) 0.6266(4) 0.24532(10) 0.0523(9) Uani 1 1 d . . . . .
H1 H 0.8835 0.5632 0.2627 0.063 Uiso 1 1 calc R . . . .
N2 N 1.1821(7) 0.6821(6) 0.20634(18) 0.0816(14) Uani 1 1 d . . . . .
H2A H 1.151(8) 0.765(6) 0.1941(19) 0.098 Uiso 1 1 d R . . . .
H2B H 1.166(8) 0.686(7) 0.2359(19) 0.098 Uiso 1 1 d R . . . .
C1 C 0.3620(7) 0.4453(7) 0.4134(2) 0.097(2) Uani 1 1 d . . . . .
H1A H 0.2965 0.5088 0.3933 0.116 Uiso 1 1 calc R . . . .
C2 C 0.3552(6) 0.4389(6) 0.4650(2) 0.0824(16) Uani 1 1 d . . . . .
H2 H 0.2848 0.4987 0.4850 0.099 Uiso 1 1 calc R . . . .
C3 C 0.4730(6) 0.3273(5) 0.47949(17) 0.0639(12) Uani 1 1 d . . . . .
H3 H 0.4951 0.2988 0.5113 0.077 Uiso 1 1 calc R . . . .
C4 C 0.5525(6) 0.2651(5) 0.43908(18) 0.0652(12) Uani 1 1 d . . . . .
H4 H 0.6364 0.1875 0.4393 0.078 Uiso 1 1 calc R . . . .
C5 C 0.4884(7) 0.3354(7) 0.39909(18) 0.0786(16) Uani 1 1 d . . . . .
H5 H 0.5222 0.3147 0.3674 0.094 Uiso 1 1 calc R . . . .
C6 C 0.6659(6) 0.7142(4) 0.42893(13) 0.0498(10) Uani 1 1 d . . . . .
H6 H 0.5902 0.7881 0.4165 0.060 Uiso 1 1 calc R . . . .
C7 C 0.6914(6) 0.6800(5) 0.47855(13) 0.0533(11) Uani 1 1 d . . . . .
H7 H 0.6356 0.7278 0.5044 0.064 Uiso 1 1 calc R . . . .
C8 C 0.8149(5) 0.5618(5) 0.48186(13) 0.0515(10) Uani 1 1 d . . . . .
H8 H 0.8548 0.5168 0.5103 0.062 Uiso 1 1 calc R . . . .
C9 C 0.8686(4) 0.5226(4) 0.43447(11) 0.0432(8) Uani 1 1 d . . . . .
H9 H 0.9508 0.4479 0.4264 0.052 Uiso 1 1 calc R . . . .
C10 C 0.7759(5) 0.6162(4) 0.40156(12) 0.0404(8) Uani 1 1 d . . . . .
C11 C 0.7950(5) 0.6052(4) 0.34783(12) 0.0434(9) Uani 1 1 d . . . . .
C12 C 0.6964(5) 0.7063(4) 0.31864(12) 0.0458(9) Uani 1 1 d . . . . .
H12 H 0.6144 0.7697 0.3337 0.055 Uiso 1 1 calc R . . . .
C13 C 0.7145(5) 0.7167(4) 0.26906(13) 0.0444(9) Uani 1 1 d . . . . .
C14 C 0.6135(6) 0.8346(5) 0.24115(14) 0.0670(12) Uani 1 1 d . . . . .
H14A H 0.6940 0.8917 0.2213 0.101 Uiso 1 1 calc GR . . . .
H14B H 0.5547 0.9020 0.2633 0.101 Uiso 1 1 calc GR . . . .
H14C H 0.5270 0.7854 0.2210 0.101 Uiso 1 1 calc GR . . . .
C15 C 0.8594(5) 0.6206(4) 0.19315(11) 0.0444(9) Uani 1 1 d . . . . .
H15 H 0.8397 0.7220 0.1795 0.053 Uiso 1 1 calc R . . . .
C16 C 1.0533(5) 0.5771(4) 0.18552(13) 0.0494(9) Uani 1 1 d . . . . .
H16 H 1.0719 0.4774 0.2006 0.059 Uiso 1 1 calc R . . . .
C17 C 1.0907(6) 0.5603(5) 0.13151(15) 0.0644(12) Uani 1 1 d . . . . .
H17A H 1.0800 0.6592 0.1162 0.077 Uiso 1 1 calc R . . . .
H17B H 1.2117 0.5256 0.1271 0.077 Uiso 1 1 calc R . . . .
C18 C 0.9675(7) 0.4508(5) 0.10707(14) 0.0694(14) Uani 1 1 d . . . . .
H18A H 0.9874 0.3493 0.1197 0.083 Uiso 1 1 calc R . . . .
H18B H 0.9928 0.4489 0.0727 0.083 Uiso 1 1 calc R . . . .
C19 C 0.7764(5) 0.4943(7) 0.11476(13) 0.0675(11) Uani 1 1 d . . . . .
H19A H 0.7001 0.4176 0.1005 0.081 Uiso 1 1 calc R . . . .
H19B H 0.7526 0.5905 0.0988 0.081 Uiso 1 1 calc R . . . .
C20 C 0.7355(5) 0.5088(6) 0.16834(12) 0.0588(9) Uani 1 1 d . . . . .
H20A H 0.7467 0.4097 0.1835 0.071 Uiso 1 1 calc R . . . .
H20B H 0.6140 0.5427 0.1724 0.071 Uiso 1 1 calc R . . . .


_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 2.023(4) . ?
Fe1 C2 2.027(4) . ?
Fe1 C3 2.038(4) . ?
Fe1 C4 2.040(4) . ?
Fe1 C5 2.016(4) . ?
Fe1 C6 2.033(4) . ?
Fe1 C7 2.042(4) . ?
Fe1 C8 2.037(4) . ?
Fe1 C9 2.034(3) . ?
Fe1 C10 2.032(3) . ?
O1 C11 1.248(4) . ?
N1 H1 0.8600 . ?
N1 C13 1.321(5) . ?
N1 C15 1.468(4) . ?
N2 H2A 0.84(5) . ?
N2 H2B 0.83(5) . ?
N2 C16 1.458(6) . ?
C1 H1A 0.9300 . ?
C1 C2 1.429(8) . ?
C1 C5 1.413(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.383(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.356(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.418(5) . ?
C6 C10 1.415(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.398(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.414(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.412(5) . ?
C10 C11 1.496(5) . ?
C11 C12 1.412(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(5) . ?
C13 C14 1.500(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9800 . ?
C15 C16 1.526(5) . ?
C15 C20 1.520(6) . ?
C16 H16 0.9800 . ?
C16 C17 1.527(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.499(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.506(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.519(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

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 C2 41.3(2) . . ?
C1 Fe1 C3 67.7(2) . . ?
C1 Fe1 C4 67.4(2) . . ?
C1 Fe1 C6 109.9(2) . . ?
C1 Fe1 C7 130.9(2) . . ?
C1 Fe1 C8 168.1(2) . . ?
C1 Fe1 C9 150.6(2) . . ?
C1 Fe1 C10 118.2(2) . . ?
C2 Fe1 C3 39.77(19) . . ?
C2 Fe1 C4 67.2(2) . . ?
C2 Fe1 C6 119.8(2) . . ?
C2 Fe1 C7 109.6(2) . . ?
C2 Fe1 C8 128.5(2) . . ?
C2 Fe1 C9 165.8(2) . . ?
C2 Fe1 C10 152.8(2) . . ?
C3 Fe1 C4 39.61(17) . . ?
C3 Fe1 C7 118.64(17) . . ?
C4 Fe1 C7 150.40(18) . . ?
C5 Fe1 C1 41.0(2) . . ?
C5 Fe1 C2 68.3(2) . . ?
C5 Fe1 C3 66.67(19) . . ?
C5 Fe1 C4 39.06(19) . . ?
C5 Fe1 C6 130.8(2) . . ?
C5 Fe1 C7 169.8(2) . . ?
C5 Fe1 C8 149.1(2) . . ?
C5 Fe1 C9 116.67(19) . . ?
C5 Fe1 C10 108.50(18) . . ?
C6 Fe1 C3 152.37(17) . . ?
C6 Fe1 C4 167.17(17) . . ?
C6 Fe1 C7 40.72(15) . . ?
C6 Fe1 C8 68.14(16) . . ?
C6 Fe1 C9 68.16(17) . . ?
C8 Fe1 C3 108.22(18) . . ?
C8 Fe1 C4 117.21(18) . . ?
C8 Fe1 C7 40.09(17) . . ?
C9 Fe1 C3 128.00(18) . . ?
C9 Fe1 C4 107.66(17) . . ?
C9 Fe1 C7 67.92(16) . . ?
C9 Fe1 C8 40.66(13) . . ?
C10 Fe1 C3 165.71(18) . . ?
C10 Fe1 C4 128.33(17) . . ?
C10 Fe1 C6 40.75(15) . . ?
C10 Fe1 C7 68.48(15) . . ?
C10 Fe1 C8 68.52(14) . . ?
C10 Fe1 C9 40.64(14) . . ?
C13 N1 H1 115.7 . . ?
C13 N1 C15 128.5(3) . . ?
C15 N1 H1 115.7 . . ?
H2A N2 H2B 109(6) . . ?
C16 N2 H2A 102(4) . . ?
C16 N2 H2B 108(4) . . ?
Fe1 C1 H1A 125.8 . . ?
C2 C1 Fe1 69.5(3) . . ?
C2 C1 H1A 127.0 . . ?
C5 C1 Fe1 69.3(3) . . ?
C5 C1 H1A 127.0 . . ?
C5 C1 C2 106.1(5) . . ?
Fe1 C2 H2 125.5 . . ?
C1 C2 Fe1 69.2(3) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 Fe1 70.5(3) . . ?
C3 C2 C1 107.1(5) . . ?
C3 C2 H2 126.4 . . ?
Fe1 C3 H3 126.1 . . ?
C2 C3 Fe1 69.7(3) . . ?
C2 C3 H3 125.5 . . ?
C4 C3 Fe1 70.3(2) . . ?
C4 C3 C2 109.0(5) . . ?
C4 C3 H3 125.5 . . ?
Fe1 C4 H4 126.4 . . ?
C3 C4 Fe1 70.1(2) . . ?
C3 C4 H4 125.5 . . ?
C5 C4 Fe1 69.5(3) . . ?
C5 C4 C3 108.9(5) . . ?
C5 C4 H4 125.5 . . ?
Fe1 C5 H5 124.8 . . ?
C1 C5 Fe1 69.8(3) . . ?
C1 C5 H5 125.5 . . ?
C4 C5 Fe1 71.4(3) . . ?
C4 C5 C1 108.9(5) . . ?
C4 C5 H5 125.5 . . ?
Fe1 C6 H6 126.0 . . ?
C7 C6 Fe1 70.0(2) . . ?
C7 C6 H6 126.0 . . ?
C10 C6 Fe1 69.6(2) . . ?
C10 C6 H6 126.0 . . ?
C10 C6 C7 108.0(4) . . ?
Fe1 C7 H7 126.6 . . ?
C6 C7 Fe1 69.3(2) . . ?
C6 C7 H7 125.9 . . ?
C8 C7 Fe1 69.8(2) . . ?
C8 C7 C6 108.1(4) . . ?
C8 C7 H7 125.9 . . ?
Fe1 C8 H8 125.9 . . ?
C7 C8 Fe1 70.2(2) . . ?
C7 C8 H8 125.9 . . ?
C7 C8 C9 108.1(3) . . ?
C9 C8 Fe1 69.56(19) . . ?
C9 C8 H8 125.9 . . ?
Fe1 C9 H9 126.3 . . ?
C8 C9 Fe1 69.8(2) . . ?
C8 C9 H9 125.9 . . ?
C10 C9 Fe1 69.6(2) . . ?
C10 C9 C8 108.3(3) . . ?
C10 C9 H9 125.9 . . ?
C6 C10 Fe1 69.7(2) . . ?
C6 C10 C11 128.8(3) . . ?
C9 C10 Fe1 69.77(19) . . ?
C9 C10 C6 107.4(3) . . ?
C9 C10 C11 123.7(3) . . ?
C11 C10 Fe1 125.0(3) . . ?
O1 C11 C10 117.7(3) . . ?
O1 C11 C12 123.7(3) . . ?
C12 C11 C10 118.4(3) . . ?
C11 C12 H12 118.1 . . ?
C13 C12 C11 123.8(3) . . ?
C13 C12 H12 118.1 . . ?
N1 C13 C12 121.1(3) . . ?
N1 C13 C14 118.5(3) . . ?
C12 C13 C14 120.4(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 H15 108.6 . . ?
N1 C15 C16 108.5(3) . . ?
N1 C15 C20 110.9(3) . . ?
C16 C15 H15 108.6 . . ?
C20 C15 H15 108.6 . . ?
C20 C15 C16 111.4(3) . . ?
N2 C16 C15 115.2(3) . . ?
N2 C16 H16 107.6 . . ?
N2 C16 C17 108.9(4) . . ?
C15 C16 H16 107.6 . . ?
C15 C16 C17 109.7(3) . . ?
C17 C16 H16 107.6 . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C16 112.9(4) . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
C17 C18 C19 111.5(4) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 C20 110.7(3) . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C15 C20 H20A 109.3 . . ?
C15 C20 H20B 109.3 . . ?
C19 C20 C15 111.7(4) . . ?
C19 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?

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 O1 0.86 1.96 2.658(4) 137.2 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 C1 C2 C3 -60.6(3) . . . . ?
Fe1 C1 C5 C4 61.0(3) . . . . ?
Fe1 C2 C3 C4 -59.5(3) . . . . ?
Fe1 C3 C4 C5 -58.8(3) . . . . ?
Fe1 C4 C5 C1 -60.0(3) . . . . ?
Fe1 C6 C7 C8 59.1(3) . . . . ?
Fe1 C6 C10 C9 -59.8(2) . . . . ?
Fe1 C6 C10 C11 119.1(4) . . . . ?
Fe1 C7 C8 C9 59.4(3) . . . . ?
Fe1 C8 C9 C10 59.1(2) . . . . ?
Fe1 C9 C10 C6 59.7(3) . . . . ?
Fe1 C9 C10 C11 -119.3(3) . . . . ?
Fe1 C10 C11 O1 -90.5(4) . . . . ?
Fe1 C10 C11 C12 92.9(4) . . . . ?
O1 C11 C12 C13 -2.5(6) . . . . ?
N1 C15 C16 N2 -60.2(4) . . . . ?
N1 C15 C16 C17 176.5(3) . . . . ?
N1 C15 C20 C19 -176.8(4) . . . . ?
N2 C16 C17 C18 178.5(4) . . . . ?
C1 C2 C3 Fe1 59.7(3) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C1 C5 Fe1 -60.1(3) . . . . ?
C2 C1 C5 C4 0.9(5) . . . . ?
C2 C3 C4 Fe1 59.2(3) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C3 C4 C5 Fe1 59.2(3) . . . . ?
C3 C4 C5 C1 -0.8(5) . . . . ?
C5 C1 C2 Fe1 59.9(3) . . . . ?
C5 C1 C2 C3 -0.7(5) . . . . ?
C6 C7 C8 Fe1 -58.9(3) . . . . ?
C6 C7 C8 C9 0.6(4) . . . . ?
C6 C10 C11 O1 178.4(4) . . . . ?
C6 C10 C11 C12 1.8(6) . . . . ?
C7 C6 C10 Fe1 59.7(3) . . . . ?
C7 C6 C10 C9 -0.1(4) . . . . ?
C7 C6 C10 C11 178.8(4) . . . . ?
C7 C8 C9 Fe1 -59.8(3) . . . . ?
C7 C8 C9 C10 -0.7(4) . . . . ?
C8 C9 C10 Fe1 -59.3(2) . . . . ?
C8 C9 C10 C6 0.5(4) . . . . ?
C8 C9 C10 C11 -178.5(3) . . . . ?
C9 C10 C11 O1 -2.8(5) . . . . ?
C9 C10 C11 C12 -179.4(3) . . . . ?
C10 C6 C7 Fe1 -59.4(3) . . . . ?
C10 C6 C7 C8 -0.3(5) . . . . ?
C10 C11 C12 C13 173.9(4) . . . . ?
C11 C12 C13 N1 2.1(6) . . . . ?
C11 C12 C13 C14 -175.8(4) . . . . ?
C13 N1 C15 C16 147.1(4) . . . . ?
C13 N1 C15 C20 -90.2(5) . . . . ?
C15 N1 C13 C12 179.4(4) . . . . ?
C15 N1 C13 C14 -2.6(6) . . . . ?
C15 C16 C17 C18 -54.6(4) . . . . ?
C16 C15 C20 C19 -55.9(5) . . . . ?
C16 C17 C18 C19 55.8(5) . . . . ?
C17 C18 C19 C20 -55.2(6) . . . . ?
C18 C19 C20 C15 55.6(6) . . . . ?
C20 C15 C16 N2 177.4(4) . . . . ?
C20 C15 C16 C17 54.1(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_test
_database_code_depnum_ccdc_archive 'CCDC 2129662'
loop_
_audit_author_name
_audit_author_address
'Mauricio Fuentealba'
;Pontificia Universidad Catolica de Valparaiso
Chile
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-02-02 downloaded from the CCDC.
;
_audit_creation_date             2020-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H28 Fe N2 O2, C3 H8 O'
_chemical_formula_sum            'C28 H36 Fe N2 O3'
_chemical_formula_weight         504.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   10.2197(6)
_cell_length_b                   10.3087(5)
_cell_length_c                   25.1548(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2650.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9553
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.17
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  0.9668
_exptl_absorpt_correction_T_min  0.8480
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0612 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.8771. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.098
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0173
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            88090
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_min         2.135
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.762
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4801
_reflns_number_total             5444
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'Apex3 v2017.3-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.414
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 1899 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         5444
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0617P)²+0.5146P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Shared sites
{O3, O3A}
{C26, C28A}
{C26A, C28}
3. Restrained distances
 C26-C27 = C27-C28
 1.498 with sigma of 0.01
 C26A-C27A = C27A-C28A
 1.498 with sigma of 0.01
 O3-C27
 1.429 with sigma of 0.01
 O3A-C27A
 1.429 with sigma of 0.01
 C26-C28
 2.435 with sigma of 0.004
 C26A-C28A
 2.435 with sigma of 0.004
 O3-C26
 2.348 with sigma of 0.004
 O3-C28
 2.348 with sigma of 0.004
 O3A-C26A
 2.348 with sigma of 0.004
 O3A-C28A
 2.348 with sigma of 0.004
4. Uiso/Uaniso restraints and constraints
Uanis(C28A) \\sim Ueq, Uanis(C26) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C26A) \\sim Ueq, Uanis(C28) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C27A) = Uanis(C27)
Uanis(C28A) = Uanis(C26)
Uanis(C26) = Uanis(C28A)
Uanis(C26A) = Uanis(C28)
Uanis(O3) = Uanis(O3A)
5. Others
 Sof(C26A)=Sof(H)=Sof(HA)=Sof(HB)=Sof(C27A)=Sof(HC)=Sof(C28A)=Sof(HD)=Sof(HE)=
 Sof(HF)=Sof(O3A)=Sof(HG)=1-FVAR(1)
 Sof(O3)=Sof(H3A)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=Sof(C27)=Sof(H27)=
 Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C20(H20), C25(H25), C27(H27), C27A(HC)
6.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
6.c Me refined with riding coordinates:
 C28(H28A,H28B,H28C), C26(H26A,H26B,H26C), C26A(H,HA,HB), C28A(HD,HE,HF)
6.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2C), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8),
 C9(H9), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19)
6.e Tetrahedral OH refined with riding coordinates:
 O3(H3A), O3A(HG)
6.f Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.35353(5) 0.65012(5) 0.23559(2) 0.04823(16) Uani 1 1 d . . . . .
O1 O 0.3312(3) 0.8188(2) 0.09899(9) 0.0474(6) Uani 1 1 d . . . . .
O2 O 0.0196(3) 0.1908(2) -0.07995(10) 0.0468(6) Uani 1 1 d . . . . .
H2 H 0.049270 0.122685 -0.068174 0.070 Uiso 1 1 calc GR . . . .
N1 N 0.2278(3) 0.7386(2) 0.00702(10) 0.0384(6) Uani 1 1 d . . . . .
H1 H 0.213195 0.803811 0.027482 0.046 Uiso 1 1 calc R . . . .
N2 N 0.1032(3) 0.9605(3) -0.04259(15) 0.0478(7) Uani 1 1 d . . . . .
H2A H 0.050(5) 0.910(4) -0.0602(18) 0.057 Uiso 1 1 d R . . . .
H2B H 0.092(4) 0.970(4) -0.0069(18) 0.057 Uiso 1 1 d R . . . .
C1 C 0.2216(5) 0.7709(6) 0.2709(2) 0.0826(14) Uani 1 1 d . . . . .
H1A H 0.216095 0.860190 0.266024 0.099 Uiso 1 1 calc R . . . .
C2 C 0.2933(6) 0.7119(7) 0.30874(17) 0.0876(17) Uani 1 1 d . . . . .
H2C H 0.345977 0.752985 0.333747 0.105 Uiso 1 1 calc R . . . .
C3 C 0.2753(7) 0.5802(8) 0.3040(2) 0.099(2) Uani 1 1 d . . . . .
H3 H 0.312721 0.517657 0.325860 0.119 Uiso 1 1 calc R . . . .
C4 C 0.1913(7) 0.5546(7) 0.2608(3) 0.111(2) Uani 1 1 d . . . . .
H4 H 0.164090 0.474121 0.248241 0.133 Uiso 1 1 calc R . . . .
C5 C 0.1574(5) 0.6795(7) 0.24048(19) 0.0918(18) Uani 1 1 d . . . . .
H5 H 0.102015 0.696276 0.211948 0.110 Uiso 1 1 calc R . . . .
C6 C 0.4802(4) 0.7573(4) 0.19059(14) 0.0498(8) Uani 1 1 d . . . . .
H6 H 0.478740 0.846785 0.185901 0.060 Uiso 1 1 calc R . . . .
C7 C 0.5493(4) 0.6908(5) 0.23058(17) 0.0627(10) Uani 1 1 d . . . . .
H7 H 0.600469 0.728430 0.256973 0.075 Uiso 1 1 calc R . . . .
C8 C 0.5272(4) 0.5567(5) 0.22351(14) 0.0615(11) Uani 1 1 d . . . . .
H8 H 0.561746 0.490692 0.244444 0.074 Uiso 1 1 calc R . . . .
C9 C 0.4439(4) 0.5396(3) 0.17937(13) 0.0497(8) Uani 1 1 d . . . . .
H9 H 0.414183 0.460761 0.166099 0.060 Uiso 1 1 calc R . . . .
C10 C 0.4131(3) 0.6655(3) 0.15859(12) 0.0400(7) Uani 1 1 d . . . . .
C11 C 0.3339(3) 0.7017(3) 0.11164(11) 0.0358(6) Uani 1 1 d . . . . .
C12 C 0.2733(3) 0.6024(3) 0.08116(12) 0.0370(7) Uani 1 1 d . . . . .
H12 H 0.263189 0.521171 0.096730 0.044 Uiso 1 1 calc R . . . .
C13 C 0.2287(3) 0.6191(3) 0.02996(12) 0.0342(6) Uani 1 1 d . . . . .
C14 C 0.1776(3) 0.5075(3) -0.00075(12) 0.0347(6) Uani 1 1 d . . . . .
C15 C 0.2385(3) 0.3876(3) 0.00254(13) 0.0417(7) Uani 1 1 d . . . . .
H15 H 0.314252 0.378621 0.022679 0.050 Uiso 1 1 calc R . . . .
C16 C 0.1873(3) 0.2807(3) -0.02402(14) 0.0427(7) Uani 1 1 d . . . . .
H16 H 0.229480 0.200934 -0.021718 0.051 Uiso 1 1 calc R . . . .
C17 C 0.0741(3) 0.2922(3) -0.05384(12) 0.0367(7) Uani 1 1 d . . . . .
C18 C 0.0140(3) 0.4124(3) -0.05776(14) 0.0423(7) Uani 1 1 d . . . . .
H18 H -0.061441 0.421429 -0.078077 0.051 Uiso 1 1 calc R . . . .
C19 C 0.0649(3) 0.5182(3) -0.03197(13) 0.0399(7) Uani 1 1 d . . . . .
H19 H 0.023803 0.598246 -0.035288 0.048 Uiso 1 1 calc R . . . .
C20 C 0.2494(3) 0.7660(3) -0.04952(12) 0.0367(7) Uani 1 1 d . . . . .
H20 H 0.182569 0.721240 -0.070596 0.044 Uiso 1 1 calc R . . . .
C21 C 0.3839(4) 0.7200(4) -0.06686(15) 0.0564(10) Uani 1 1 d . . . . .
H21A H 0.388711 0.626424 -0.063428 0.068 Uiso 1 1 calc R . . . .
H21B H 0.449705 0.757606 -0.043746 0.068 Uiso 1 1 calc R . . . .
C22 C 0.4127(6) 0.7582(5) -0.12433(19) 0.0782(14) Uani 1 1 d . . . . .
H22A H 0.500452 0.730942 -0.133820 0.094 Uiso 1 1 calc R . . . .
H22B H 0.351553 0.714944 -0.147916 0.094 Uiso 1 1 calc R . . . .
C23 C 0.4004(5) 0.9044(4) -0.1309(2) 0.0737(14) Uani 1 1 d . . . . .
H23A H 0.467280 0.946975 -0.109781 0.088 Uiso 1 1 calc R . . . .
H23B H 0.414623 0.927195 -0.167827 0.088 Uiso 1 1 calc R . . . .
C24 C 0.2666(4) 0.9519(4) -0.11355(15) 0.0534(9) Uani 1 1 d . . . . .
H24A H 0.263811 1.045734 -0.116390 0.064 Uiso 1 1 calc R . . . .
H24B H 0.200776 0.916753 -0.137286 0.064 Uiso 1 1 calc R . . . .
C25 C 0.2344(3) 0.9128(3) -0.05699(13) 0.0370(7) Uani 1 1 d . . . . .
H25 H 0.297750 0.955468 -0.033513 0.044 Uiso 1 1 calc R . . . .
O3 O 0.1455(5) 1.0193(3) 0.08132(13) 0.0976(12) Uani 0.580(10) 1 d D . P A 1
H3A H 0.198092 0.965528 0.092277 0.146 Uiso 0.580(10) 1 calc R . P A 1
C28 C 0.0209(8) 1.2008(6) 0.1062(3) 0.154(4) Uani 0.580(10) 1 d D U P A 1
H28A H -0.017682 1.244888 0.135902 0.231 Uiso 0.580(10) 1 calc R . P A 1
H28B H 0.082227 1.257313 0.088887 0.231 Uiso 0.580(10) 1 calc R . P A 1
H28C H -0.046448 1.176528 0.081473 0.231 Uiso 0.580(10) 1 calc R . P A 1
C27 C 0.0886(10) 1.0847(9) 0.1248(3) 0.079(2) Uani 0.580(10) 1 d D . P A 1
H27 H 0.020639 1.026768 0.138660 0.095 Uiso 0.580(10) 1 calc R . P A 1
C26 C 0.1796(11) 1.1032(10) 0.1670(3) 0.198(5) Uani 0.580(10) 1 d D U P A 1
H26A H 0.137410 1.147854 0.195749 0.297 Uiso 0.580(10) 1 calc R . P A 1
H26B H 0.210460 1.020411 0.179154 0.297 Uiso 0.580(10) 1 calc R . P A 1
H26C H 0.252190 1.153783 0.154476 0.297 Uiso 0.580(10) 1 calc R . P A 1
C26A C 0.0209(8) 1.2008(6) 0.1062(3) 0.154(4) Uani 0.420(10) 1 d D U P A 2
H H 0.021039 1.276200 0.128552 0.231 Uiso 0.420(10) 1 calc R . P A 2
HA H 0.012881 1.226956 0.069682 0.231 Uiso 0.420(10) 1 calc R . P A 2
HB H -0.051602 1.146098 0.115503 0.231 Uiso 0.420(10) 1 calc R . P A 2
C27A C 0.1434(13) 1.1292(11) 0.1134(4) 0.079(2) Uani 0.420(10) 1 d D . P A 2
HC H 0.212082 1.186048 0.099402 0.095 Uiso 0.420(10) 1 calc R . P A 2
C28A C 0.1796(11) 1.1032(10) 0.1670(3) 0.198(5) Uani 0.420(10) 1 d D U P A 2
HD H 0.176425 1.182087 0.187207 0.297 Uiso 0.420(10) 1 calc R . P A 2
HE H 0.119964 1.041261 0.182004 0.297 Uiso 0.420(10) 1 calc R . P A 2
HF H 0.266781 1.068632 0.167854 0.297 Uiso 0.420(10) 1 calc R . P A 2
O3A O 0.1455(5) 1.0193(3) 0.08132(13) 0.0976(12) Uani 0.420(10) 1 d D . P A 2
HG H 0.182764 0.960186 0.097012 0.146 Uiso 0.420(10) 1 calc R . P A 2


_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 2.039(5) . ?
Fe1 C2 2.042(4) . ?
Fe1 C3 2.029(5) . ?
Fe1 C4 2.029(5) . ?
Fe1 C5 2.031(5) . ?
Fe1 C6 2.044(4) . ?
Fe1 C7 2.048(4) . ?
Fe1 C8 2.042(4) . ?
Fe1 C9 2.037(3) . ?
Fe1 C10 2.036(3) . ?
O1 C11 1.249(4) . ?
O2 H2 0.8200 . ?
O2 C17 1.354(4) . ?
N1 H1 0.8600 . ?
N1 C13 1.360(4) . ?
N1 C20 1.467(4) . ?
N2 H2A 0.87(5) . ?
N2 H2B 0.91(4) . ?
N2 C25 1.473(5) . ?
C1 H1A 0.9300 . ?
C1 C2 1.347(7) . ?
C1 C5 1.380(8) . ?
C2 H2C 0.9300 . ?
C2 C3 1.375(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.409(9) . ?
C4 H4 0.9300 . ?
C4 C5 1.428(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.408(6) . ?
C6 C10 1.419(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.412(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.410(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.434(5) . ?
C10 C11 1.479(4) . ?
C11 C12 1.421(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.377(4) . ?
C13 C14 1.481(4) . ?
C14 C15 1.386(4) . ?
C14 C19 1.398(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.391(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(5) . ?
C17 C18 1.387(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.371(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9800 . ?
C20 C21 1.518(5) . ?
C20 C25 1.533(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.527(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.521(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.517(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.515(5) . ?
C25 H25 0.9800 . ?
O3 H3A 0.8200 . ?
O3 C27 1.409(8) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C28 C27 1.460(9) . ?
C27 H27 0.9800 . ?
C27 C26 1.425(9) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C26A H 0.9600 . ?
C26A HA 0.9600 . ?
C26A HB 0.9600 . ?
C26A C27A 1.464(10) . ?
C27A HC 0.9800 . ?
C27A C28A 1.423(10) . ?
C27A O3A 1.392(10) . ?
C28A HD 0.9600 . ?
C28A HE 0.9600 . ?
C28A HF 0.9600 . ?
O3A HG 0.8200 . ?

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 C2 38.5(2) . . ?
C1 Fe1 C6 109.3(2) . . ?
C1 Fe1 C7 123.2(2) . . ?
C1 Fe1 C8 158.1(2) . . ?
C2 Fe1 C6 121.4(2) . . ?
C2 Fe1 C7 106.6(2) . . ?
C3 Fe1 C1 65.6(3) . . ?
C3 Fe1 C2 39.5(3) . . ?
C3 Fe1 C4 40.6(3) . . ?
C3 Fe1 C5 67.2(2) . . ?
C3 Fe1 C6 155.6(3) . . ?
C3 Fe1 C7 120.6(2) . . ?
C3 Fe1 C8 107.5(2) . . ?
C3 Fe1 C9 124.6(2) . . ?
C3 Fe1 C10 162.1(3) . . ?
C4 Fe1 C1 67.7(3) . . ?
C4 Fe1 C2 67.9(3) . . ?
C4 Fe1 C5 41.2(3) . . ?
C4 Fe1 C6 162.3(3) . . ?
C4 Fe1 C7 156.4(3) . . ?
C4 Fe1 C8 121.8(3) . . ?
C4 Fe1 C9 108.4(2) . . ?
C4 Fe1 C10 125.4(2) . . ?
C5 Fe1 C1 39.6(2) . . ?
C5 Fe1 C2 66.5(2) . . ?
C5 Fe1 C6 125.3(2) . . ?
C5 Fe1 C7 159.6(2) . . ?
C5 Fe1 C8 159.6(3) . . ?
C5 Fe1 C9 125.0(2) . . ?
C5 Fe1 C10 109.93(17) . . ?
C6 Fe1 C7 40.25(16) . . ?
C8 Fe1 C2 122.9(2) . . ?
C8 Fe1 C6 67.80(17) . . ?
C8 Fe1 C7 40.38(19) . . ?
C9 Fe1 C1 160.67(19) . . ?
C9 Fe1 C2 159.5(2) . . ?
C9 Fe1 C6 68.33(15) . . ?
C9 Fe1 C7 68.21(17) . . ?
C9 Fe1 C8 40.45(16) . . ?
C10 Fe1 C1 124.37(19) . . ?
C10 Fe1 C2 157.4(2) . . ?
C10 Fe1 C6 40.71(13) . . ?
C10 Fe1 C7 68.52(15) . . ?
C10 Fe1 C8 68.63(14) . . ?
C10 Fe1 C9 41.22(13) . . ?
C17 O2 H2 109.5 . . ?
C13 N1 H1 117.1 . . ?
C13 N1 C20 125.8(2) . . ?
C20 N1 H1 117.1 . . ?
H2A N2 H2B 119(4) . . ?
C25 N2 H2A 104(3) . . ?
C25 N2 H2B 113(3) . . ?
Fe1 C1 H1A 125.9 . . ?
C2 C1 Fe1 70.8(3) . . ?
C2 C1 H1A 125.0 . . ?
C2 C1 C5 110.0(6) . . ?
C5 C1 Fe1 69.9(3) . . ?
C5 C1 H1A 125.0 . . ?
Fe1 C2 H2C 125.3 . . ?
C1 C2 Fe1 70.6(3) . . ?
C1 C2 H2C 125.9 . . ?
C1 C2 C3 108.2(6) . . ?
C3 C2 Fe1 69.8(3) . . ?
C3 C2 H2C 125.9 . . ?
Fe1 C3 H3 125.9 . . ?
C2 C3 Fe1 70.8(3) . . ?
C2 C3 H3 125.3 . . ?
C2 C3 C4 109.5(6) . . ?
C4 C3 Fe1 69.7(3) . . ?
C4 C3 H3 125.3 . . ?
Fe1 C4 H4 124.9 . . ?
C3 C4 Fe1 69.7(3) . . ?
C3 C4 H4 127.6 . . ?
C3 C4 C5 104.8(6) . . ?
C5 C4 Fe1 69.5(3) . . ?
C5 C4 H4 127.6 . . ?
Fe1 C5 H5 125.5 . . ?
C1 C5 Fe1 70.5(3) . . ?
C1 C5 C4 107.6(5) . . ?
C1 C5 H5 126.2 . . ?
C4 C5 Fe1 69.3(3) . . ?
C4 C5 H5 126.2 . . ?
Fe1 C6 H6 126.6 . . ?
C7 C6 Fe1 70.0(2) . . ?
C7 C6 H6 125.6 . . ?
C7 C6 C10 108.8(3) . . ?
C10 C6 Fe1 69.35(19) . . ?
C10 C6 H6 125.6 . . ?
Fe1 C7 H7 126.2 . . ?
C6 C7 Fe1 69.7(2) . . ?
C6 C7 H7 126.1 . . ?
C6 C7 C8 107.9(4) . . ?
C8 C7 Fe1 69.6(3) . . ?
C8 C7 H7 126.1 . . ?
Fe1 C8 H8 126.2 . . ?
C7 C8 Fe1 70.0(2) . . ?
C7 C8 H8 125.7 . . ?
C9 C8 Fe1 69.6(2) . . ?
C9 C8 C7 108.5(3) . . ?
C9 C8 H8 125.7 . . ?
Fe1 C9 H9 126.2 . . ?
C8 C9 Fe1 70.0(2) . . ?
C8 C9 H9 126.1 . . ?
C8 C9 C10 107.9(3) . . ?
C10 C9 Fe1 69.37(19) . . ?
C10 C9 H9 126.1 . . ?
C6 C10 Fe1 69.93(19) . . ?
C6 C10 C9 106.9(3) . . ?
C6 C10 C11 123.3(3) . . ?
C9 C10 Fe1 69.41(18) . . ?
C9 C10 C11 129.8(3) . . ?
C11 C10 Fe1 128.0(2) . . ?
O1 C11 C10 117.4(3) . . ?
O1 C11 C12 123.3(3) . . ?
C12 C11 C10 119.2(3) . . ?
C11 C12 H12 118.0 . . ?
C13 C12 C11 124.0(3) . . ?
C13 C12 H12 118.0 . . ?
N1 C13 C12 120.8(3) . . ?
N1 C13 C14 118.6(3) . . ?
C12 C13 C14 120.5(3) . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 C19 118.2(3) . . ?
C19 C14 C13 121.5(3) . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(3) . . ?
C17 C16 H16 119.8 . . ?
O2 C17 C16 122.7(3) . . ?
O2 C17 C18 118.3(3) . . ?
C16 C17 C18 119.0(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 121.1(3) . . ?
C18 C19 H19 119.5 . . ?
N1 C20 H20 109.2 . . ?
N1 C20 C21 110.8(3) . . ?
N1 C20 C25 107.1(2) . . ?
C21 C20 H20 109.2 . . ?
C21 C20 C25 111.3(3) . . ?
C25 C20 H20 109.2 . . ?
C20 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
C20 C21 C22 111.5(3) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C21 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C23 C22 C21 110.0(4) . . ?
C23 C22 H22A 109.7 . . ?
C23 C22 H22B 109.7 . . ?
C22 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C24 C23 C22 111.3(4) . . ?
C24 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C23 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
C25 C24 C23 112.3(3) . . ?
C25 C24 H24A 109.1 . . ?
C25 C24 H24B 109.1 . . ?
N2 C25 C20 113.0(3) . . ?
N2 C25 C24 109.9(3) . . ?
N2 C25 H25 107.7 . . ?
C20 C25 H25 107.7 . . ?
C24 C25 C20 110.9(3) . . ?
C24 C25 H25 107.7 . . ?
C27 O3 H3A 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
O3 C27 C28 109.8(6) . . ?
O3 C27 H27 106.1 . . ?
O3 C27 C26 111.9(6) . . ?
C28 C27 H27 106.1 . . ?
C26 C27 C28 116.0(7) . . ?
C26 C27 H27 106.1 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
C27 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
H C26A HA 109.5 . . ?
H C26A HB 109.5 . . ?
HA C26A HB 109.5 . . ?
C27A C26A H 109.5 . . ?
C27A C26A HA 109.5 . . ?
C27A C26A HB 109.5 . . ?
C26A C27A HC 105.5 . . ?
C28A C27A C26A 115.8(8) . . ?
C28A C27A HC 105.5 . . ?
O3A C27A C26A 110.6(8) . . ?
O3A C27A HC 105.5 . . ?
O3A C27A C28A 113.0(8) . . ?
C27A C28A HD 109.5 . . ?
C27A C28A HE 109.5 . . ?
C27A C28A HF 109.5 . . ?
HD C28A HE 109.5 . . ?
HD C28A HF 109.5 . . ?
HE C28A HF 109.5 . . ?
C27A O3A HG 109.5 . . ?

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
O2 H2 N2 0.82 1.87 2.692(4) 175.1 1_545
N1 H1 O1 0.86 2.17 2.675(3) 117.1 .
N2 H2B O3 0.91(4) 2.34(4) 3.205(5) 159(4) .
N2 H2B O3A 0.91(4) 2.34(4) 3.205(5) 159(4) .
O3 H3A O1 0.82 2.04 2.841(4) 165.0 .
O3A HG O1 0.82 2.10 2.841(4) 149.5 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe1 C1 C2 C3 -59.9(4) . . . . ?
Fe1 C1 C5 C4 59.7(4) . . . . ?
Fe1 C2 C3 C4 -59.1(4) . . . . ?
Fe1 C3 C4 C5 -61.0(4) . . . . ?
Fe1 C4 C5 C1 -60.4(3) . . . . ?
Fe1 C6 C7 C8 59.3(3) . . . . ?
Fe1 C6 C10 C9 -59.9(2) . . . . ?
Fe1 C6 C10 C11 123.0(3) . . . . ?
Fe1 C7 C8 C9 59.1(3) . . . . ?
Fe1 C8 C9 C10 59.2(3) . . . . ?
Fe1 C9 C10 C6 60.2(2) . . . . ?
Fe1 C9 C10 C11 -122.9(4) . . . . ?
Fe1 C10 C11 O1 92.3(4) . . . . ?
Fe1 C10 C11 C12 -92.2(3) . . . . ?
O1 C11 C12 C13 13.6(5) . . . . ?
O2 C17 C18 C19 179.8(3) . . . . ?
N1 C13 C14 C15 141.6(3) . . . . ?
N1 C13 C14 C19 -40.9(4) . . . . ?
N1 C20 C21 C22 -175.1(3) . . . . ?
N1 C20 C25 N2 -61.1(4) . . . . ?
N1 C20 C25 C24 175.2(3) . . . . ?
C1 C2 C3 Fe1 60.5(4) . . . . ?
C1 C2 C3 C4 1.4(7) . . . . ?
C2 C1 C5 Fe1 -59.6(4) . . . . ?
C2 C1 C5 C4 0.1(6) . . . . ?
C2 C3 C4 Fe1 59.7(4) . . . . ?
C2 C3 C4 C5 -1.3(6) . . . . ?
C3 C4 C5 Fe1 61.2(4) . . . . ?
C3 C4 C5 C1 0.8(6) . . . . ?
C5 C1 C2 Fe1 59.0(4) . . . . ?
C5 C1 C2 C3 -0.9(6) . . . . ?
C6 C7 C8 Fe1 -59.4(3) . . . . ?
C6 C7 C8 C9 -0.3(5) . . . . ?
C6 C10 C11 O1 2.7(5) . . . . ?
C6 C10 C11 C12 178.2(3) . . . . ?
C7 C6 C10 Fe1 59.1(3) . . . . ?
C7 C6 C10 C9 -0.8(4) . . . . ?
C7 C6 C10 C11 -178.0(3) . . . . ?
C7 C8 C9 Fe1 -59.4(3) . . . . ?
C7 C8 C9 C10 -0.2(5) . . . . ?
C8 C9 C10 Fe1 -59.6(3) . . . . ?
C8 C9 C10 C6 0.6(4) . . . . ?
C8 C9 C10 C11 177.5(3) . . . . ?
C9 C10 C11 O1 -173.7(4) . . . . ?
C9 C10 C11 C12 1.7(5) . . . . ?
C10 C6 C7 Fe1 -58.7(3) . . . . ?
C10 C6 C7 C8 0.7(5) . . . . ?
C10 C11 C12 C13 -161.6(3) . . . . ?
C11 C12 C13 N1 -7.1(5) . . . . ?
C11 C12 C13 C14 174.5(3) . . . . ?
C12 C13 C14 C15 -39.9(4) . . . . ?
C12 C13 C14 C19 137.6(3) . . . . ?
C13 N1 C20 C21 -60.4(4) . . . . ?
C13 N1 C20 C25 178.0(3) . . . . ?
C13 C14 C15 C16 176.7(3) . . . . ?
C13 C14 C19 C18 -176.1(3) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
C15 C14 C19 C18 1.4(5) . . . . ?
C15 C16 C17 O2 -179.3(3) . . . . ?
C15 C16 C17 C18 1.4(5) . . . . ?
C16 C17 C18 C19 -0.8(5) . . . . ?
C17 C18 C19 C14 -0.6(5) . . . . ?
C19 C14 C15 C16 -0.9(5) . . . . ?
C20 N1 C13 C12 146.6(3) . . . . ?
C20 N1 C13 C14 -35.0(5) . . . . ?
C20 C21 C22 C23 56.9(6) . . . . ?
C21 C20 C25 N2 177.7(3) . . . . ?
C21 C20 C25 C24 53.9(4) . . . . ?
C21 C22 C23 C24 -56.2(6) . . . . ?
C22 C23 C24 C25 55.7(6) . . . . ?
C23 C24 C25 N2 -179.5(3) . . . . ?
C23 C24 C25 C20 -53.9(5) . . . . ?
C25 C20 C21 C22 -56.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

