# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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 
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data_32079403_0m
_database_code_depnum_ccdc_archive 'CCDC 2225832'
loop_
_audit_author_name
_audit_author_address
'Laura Valencia Matarranz'
;Universidade de Vigo
Spain
;
_audit_update_record             
;
2022-12-12 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;
_audit_creation_date             2022-11-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 Fe N4 O4, F6 P, H2 O'
_chemical_formula_sum            'C18 H20 F6 Fe N4 O5 P'
_chemical_formula_weight         573.20
_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'
F F 0.0171 0.0103 '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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.4135(5)
_cell_length_b                   10.9733(4)
_cell_length_c                   15.5664(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.6190(10)
_cell_angle_gamma                90
_cell_volume                     2116.18(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9798
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.76
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.839
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1065 before and 0.0459 after correction. The Ratio of minimum to maximum transmission is 0.9261. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.017
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43559
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_min         2.479
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Incoatec HeliosTM multilayer optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4893
_reflns_number_total             5254
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     319
_refine_ls_number_reflns         5254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0270P)²+2.0747P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0710
_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
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 N2(H2), N3(H3), C8(H8), C11(H11)
2.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C7(H7A,H7B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C14(H14), C4(H4), C16(H16), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.19840(2) 0.37999(2) 0.74071(2) 0.00874(6) Uani 1 1 d . . . . .
P1 P 0.59559(3) 0.38408(4) 0.73756(3) 0.01324(9) Uani 1 1 d . . . . .
F5 F 0.57237(9) 0.24975(9) 0.77128(7) 0.0255(2) Uani 1 1 d . . . . .
F4 F 0.52009(9) 0.44020(10) 0.80705(7) 0.0244(2) Uani 1 1 d . . . . .
F1 F 0.67184(9) 0.32797(11) 0.66772(7) 0.0279(2) Uani 1 1 d . . . . .
F3 F 0.49359(9) 0.37159(11) 0.66917(7) 0.0257(2) Uani 1 1 d . . . . .
F6 F 0.69720(9) 0.39380(11) 0.80601(7) 0.0299(3) Uani 1 1 d . . . . .
O3 O 0.30586(9) 0.25783(10) 0.78179(7) 0.0113(2) Uani 1 1 d . . . . .
O1 O 0.29575(9) 0.51572(10) 0.71511(7) 0.0108(2) Uani 1 1 d . . . . .
O4 O 0.39228(9) 0.16755(10) 0.89547(7) 0.0155(2) Uani 1 1 d . . . . .
O2 O 0.37807(9) 0.62026(10) 0.61559(7) 0.0151(2) Uani 1 1 d . . . . .
F2 F 0.61873(12) 0.51773(11) 0.70335(8) 0.0386(3) Uani 1 1 d . . . . .
O5 O 0.50174(12) 0.74613(12) 0.49722(9) 0.0256(3) Uani 1 1 d . . . . .
H5A H 0.466745 0.699945 0.531346 0.038 Uiso 1 1 d G . . . .
H5B H 0.494050 0.710325 0.447386 0.038 Uiso 1 1 d G . . . .
N4 N 0.20724(10) 0.40828(11) 0.87199(8) 0.0103(2) Uani 1 1 d . . . . .
N1 N 0.21333(10) 0.36059(12) 0.60994(8) 0.0106(2) Uani 1 1 d . . . . .
N2 N 0.08207(10) 0.23561(12) 0.70339(8) 0.0114(2) Uani 1 1 d . . . . .
H2 H 0.094785 0.168689 0.746440 0.014 Uiso 1 1 calc R . . . .
N3 N 0.06702(10) 0.51017(12) 0.75953(8) 0.0113(2) Uani 1 1 d . . . . .
H3 H 0.073019 0.575295 0.715148 0.014 Uiso 1 1 calc R . . . .
C18 C 0.33115(12) 0.24481(14) 0.86362(10) 0.0111(3) Uani 1 1 d . . . . .
C6 C 0.16144(12) 0.27302(14) 0.56436(10) 0.0122(3) Uani 1 1 d . . . . .
C3 C 0.28283(13) 0.44588(15) 0.48463(10) 0.0156(3) Uani 1 1 d . . . . .
H3A H 0.325889 0.505071 0.458359 0.019 Uiso 1 1 calc R . . . .
C2 C 0.27251(12) 0.44545(13) 0.57235(10) 0.0112(3) Uani 1 1 d . . . . .
C13 C 0.14932(12) 0.49456(14) 0.90823(10) 0.0116(3) Uani 1 1 d . . . . .
C1 C 0.32165(12) 0.53544(14) 0.63689(10) 0.0110(3) Uani 1 1 d . . . . .
C8 C -0.03321(12) 0.27045(14) 0.70647(10) 0.0134(3) Uani 1 1 d . . . . .
H8 H -0.084960 0.202998 0.690859 0.016 Uiso 1 1 calc R . . . .
C9 C -0.05982(13) 0.39206(14) 0.65909(10) 0.0149(3) Uani 1 1 d . . . . .
H9A H -0.006887 0.415090 0.616953 0.018 Uiso 1 1 calc R . . . .
H9B H -0.134551 0.396638 0.633038 0.018 Uiso 1 1 calc R . . . .
C17 C 0.27405(12) 0.33450(14) 0.91896(10) 0.0113(3) Uani 1 1 d . . . . .
C5 C 0.16620(14) 0.26912(15) 0.47533(10) 0.0162(3) Uani 1 1 d . . . . .
H5 H 0.128229 0.208264 0.442261 0.019 Uiso 1 1 calc R . . . .
C14 C 0.15739(13) 0.51029(15) 0.99741(10) 0.0154(3) Uani 1 1 d . . . . .
H14 H 0.117936 0.572698 1.023760 0.018 Uiso 1 1 calc R . . . .
C11 C -0.04335(12) 0.45879(15) 0.74626(10) 0.0136(3) Uani 1 1 d . . . . .
H11 H -0.102048 0.517963 0.757595 0.016 Uiso 1 1 calc R . . . .
C4 C 0.22760(14) 0.35605(16) 0.43584(10) 0.0179(3) Uani 1 1 d . . . . .
H4 H 0.232098 0.354441 0.375158 0.021 Uiso 1 1 calc R . . . .
C16 C 0.28422(13) 0.34281(15) 1.00730(10) 0.0157(3) Uani 1 1 d . . . . .
H16 H 0.330383 0.289271 1.040454 0.019 Uiso 1 1 calc R . . . .
C10 C -0.05405(13) 0.33459(15) 0.79215(10) 0.0149(3) Uani 1 1 d . . . . .
H10A H 0.002682 0.319663 0.838544 0.018 Uiso 1 1 calc R . . . .
H10B H -0.126782 0.319190 0.812495 0.018 Uiso 1 1 calc R . . . .
C12 C 0.08193(13) 0.57156(14) 0.84519(10) 0.0128(3) Uani 1 1 d . . . . .
H12A H 0.010484 0.586587 0.868048 0.015 Uiso 1 1 calc R . . . .
H12B H 0.117643 0.651312 0.838275 0.015 Uiso 1 1 calc R . . . .
C15 C 0.22447(14) 0.43254(16) 1.04667(10) 0.0182(3) Uani 1 1 d . . . . .
H15 H 0.229763 0.440411 1.107566 0.022 Uiso 1 1 calc R . . . .
C7 C 0.10431(13) 0.18257(14) 0.61826(10) 0.0137(3) Uani 1 1 d . . . . .
H7A H 0.035430 0.158082 0.587558 0.016 Uiso 1 1 calc R . . . .
H7B H 0.149557 0.108781 0.627008 0.016 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 O3 1.9692(11) . ?
Fe1 O1 1.9744(11) . ?
Fe1 N4 2.0631(13) . ?
Fe1 N1 2.0667(13) . ?
Fe1 N2 2.1970(13) . ?
Fe1 N3 2.2015(13) . ?
P1 F5 1.5971(11) . ?
P1 F4 1.5986(10) . ?
P1 F1 1.6084(11) . ?
P1 F3 1.6078(11) . ?
P1 F6 1.6025(11) . ?
P1 F2 1.5926(12) . ?
O3 C18 1.3005(18) . ?
O1 C1 1.2969(18) . ?
O4 C18 1.2218(19) . ?
O2 C1 1.2232(19) . ?
O5 H5A 0.8700 . ?
O5 H5B 0.8695 . ?
N4 C13 1.3353(19) . ?
N4 C17 1.342(2) . ?
N1 C6 1.336(2) . ?
N1 C2 1.3429(19) . ?
N2 H2 1.0000 . ?
N2 C8 1.4849(19) . ?
N2 C7 1.4890(19) . ?
N3 H3 1.0000 . ?
N3 C11 1.484(2) . ?
N3 C12 1.4951(19) . ?
C18 C17 1.513(2) . ?
C6 C5 1.391(2) . ?
C6 C7 1.506(2) . ?
C3 H3A 0.9500 . ?
C3 C2 1.379(2) . ?
C3 C4 1.397(2) . ?
C2 C1 1.510(2) . ?
C13 C14 1.396(2) . ?
C13 C12 1.508(2) . ?
C8 H8 1.0000 . ?
C8 C9 1.550(2) . ?
C8 C10 1.544(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C11 1.544(2) . ?
C17 C16 1.376(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.388(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.389(2) . ?
C11 H11 1.0000 . ?
C11 C10 1.548(2) . ?
C4 H4 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.397(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C15 H15 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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
O3 Fe1 O1 99.69(4) . . ?
O3 Fe1 N4 77.77(5) . . ?
O3 Fe1 N1 98.55(5) . . ?
O3 Fe1 N2 90.89(5) . . ?
O3 Fe1 N3 152.98(5) . . ?
O1 Fe1 N4 95.25(5) . . ?
O1 Fe1 N1 77.57(5) . . ?
O1 Fe1 N2 153.01(5) . . ?
O1 Fe1 N3 90.31(5) . . ?
N4 Fe1 N1 171.38(5) . . ?
N4 Fe1 N2 111.31(5) . . ?
N4 Fe1 N3 76.36(5) . . ?
N1 Fe1 N2 76.32(5) . . ?
N1 Fe1 N3 108.13(5) . . ?
N2 Fe1 N3 91.32(5) . . ?
F5 P1 F4 90.43(6) . . ?
F5 P1 F1 89.71(6) . . ?
F5 P1 F3 89.31(6) . . ?
F5 P1 F6 89.64(6) . . ?
F4 P1 F1 179.81(7) . . ?
F4 P1 F3 90.58(6) . . ?
F4 P1 F6 89.71(6) . . ?
F3 P1 F1 89.56(6) . . ?
F6 P1 F1 90.16(6) . . ?
F6 P1 F3 178.91(7) . . ?
F2 P1 F5 179.65(7) . . ?
F2 P1 F4 89.85(7) . . ?
F2 P1 F1 90.02(7) . . ?
F2 P1 F3 90.47(7) . . ?
F2 P1 F6 90.58(7) . . ?
C18 O3 Fe1 120.63(10) . . ?
C1 O1 Fe1 120.43(10) . . ?
H5A O5 H5B 104.5 . . ?
C13 N4 Fe1 121.93(10) . . ?
C13 N4 C17 121.89(13) . . ?
C17 N4 Fe1 116.18(10) . . ?
C6 N1 Fe1 121.81(10) . . ?
C6 N1 C2 121.75(13) . . ?
C2 N1 Fe1 116.31(10) . . ?
Fe1 N2 H2 106.2 . . ?
C8 N2 Fe1 115.12(9) . . ?
C8 N2 H2 106.2 . . ?
C8 N2 C7 111.26(12) . . ?
C7 N2 Fe1 111.19(9) . . ?
C7 N2 H2 106.2 . . ?
Fe1 N3 H3 106.5 . . ?
C11 N3 Fe1 114.85(9) . . ?
C11 N3 H3 106.5 . . ?
C11 N3 C12 110.89(12) . . ?
C12 N3 Fe1 111.10(9) . . ?
C12 N3 H3 106.5 . . ?
O3 C18 C17 113.16(13) . . ?
O4 C18 O3 125.38(14) . . ?
O4 C18 C17 121.44(14) . . ?
N1 C6 C5 120.12(14) . . ?
N1 C6 C7 113.99(13) . . ?
C5 C6 C7 125.86(14) . . ?
C2 C3 H3A 121.2 . . ?
C2 C3 C4 117.55(15) . . ?
C4 C3 H3A 121.2 . . ?
N1 C2 C3 121.41(14) . . ?
N1 C2 C1 111.89(13) . . ?
C3 C2 C1 126.70(14) . . ?
N4 C13 C14 120.07(14) . . ?
N4 C13 C12 114.45(13) . . ?
C14 C13 C12 125.44(14) . . ?
O1 C1 C2 113.70(13) . . ?
O2 C1 O1 124.16(14) . . ?
O2 C1 C2 122.11(14) . . ?
N2 C8 H8 114.0 . . ?
N2 C8 C9 112.52(12) . . ?
N2 C8 C10 111.08(12) . . ?
C9 C8 H8 114.0 . . ?
C10 C8 H8 114.0 . . ?
C10 C8 C9 88.65(12) . . ?
C8 C9 H9A 113.9 . . ?
C8 C9 H9B 113.9 . . ?
H9A C9 H9B 111.1 . . ?
C11 C9 C8 88.72(12) . . ?
C11 C9 H9A 113.9 . . ?
C11 C9 H9B 113.9 . . ?
N4 C17 C18 112.20(13) . . ?
N4 C17 C16 121.27(14) . . ?
C16 C17 C18 126.52(14) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 C6 118.61(15) . . ?
C4 C5 H5 120.7 . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.42(15) . . ?
C15 C14 H14 120.8 . . ?
N3 C11 C9 111.86(12) . . ?
N3 C11 H11 113.9 . . ?
N3 C11 C10 112.06(12) . . ?
C9 C11 H11 113.9 . . ?
C9 C11 C10 88.72(12) . . ?
C10 C11 H11 113.9 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.55(15) . . ?
C5 C4 H4 119.7 . . ?
C17 C16 H16 121.1 . . ?
C17 C16 C15 117.85(15) . . ?
C15 C16 H16 121.1 . . ?
C8 C10 C11 88.78(12) . . ?
C8 C10 H10A 113.9 . . ?
C8 C10 H10B 113.9 . . ?
C11 C10 H10A 113.9 . . ?
C11 C10 H10B 113.9 . . ?
H10A C10 H10B 111.1 . . ?
N3 C12 C13 111.12(12) . . ?
N3 C12 H12A 109.4 . . ?
N3 C12 H12B 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C15 C16 120.47(15) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
N2 C7 C6 111.01(12) . . ?
N2 C7 H7A 109.4 . . ?
N2 C7 H7B 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
