# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2431109'
loop_
_audit_author_name
_audit_author_address
'Luis Alves'
;Associacao do Instituto Superior Tecnico para a Investigacao e Desenvolvimento
Portugal
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2026-02-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_shelx               
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.932 Why?
RESPONSE: The crystal has poor diffracting power and low quality.
;
_vrf_PLAT213_shelx               
;
PROBLEM: Atom F3              has ADP max/min Ratio .....        4.4 prolat
RESPONSE: The disorder found in the CF3 groups were modelled but some F atoms are still elongated.
;
# Added during the CSD deposition process: Thursday 13 March 2025 02:08 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H46 F6 N4 O4'
_chemical_formula_sum            'C34 H46 F6 N4 O4'
_chemical_formula_weight         688.75

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'
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'
F F 0.0171 0.0103 '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'

_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                   5.3622(7)
_cell_length_b                   8.688(1)
_cell_length_c                   19.054(2)
_cell_angle_alpha                95.539(8)
_cell_angle_beta                 91.382(8)
_cell_angle_gamma                105.270(7)
_cell_volume                     851.19(18)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    837
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      23.51

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5551
_diffrn_reflns_av_unetI/netI     0.1024
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.075
_diffrn_reflns_theta_max         25.755
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 0.932
_reflns_number_total             3269
_reflns_number_gt                1597
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.1783P)²+0.0607P] 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         3269
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1745
_refine_ls_R_factor_gt           0.0993
_refine_ls_wR_factor_ref         0.3110
_refine_ls_wR_factor_gt          0.2686
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
N1 N 0.0745(7) 0.3119(4) 0.3858(2) 0.0286(10) Uani 1 1 d . . . . .
N2 N -0.1505(7) 0.3285(4) 0.6012(2) 0.0251(10) Uani 1 1 d . . . . .
O2 O -0.2310(7) 0.2784(5) 0.7873(2) 0.0462(11) Uani 1 1 d . . . . .
O1 O -0.5123(7) 0.1599(4) 0.6974(2) 0.0478(11) Uani 1 1 d . . . . .
C15 C -0.3026(10) 0.2446(6) 0.7192(3) 0.0310(12) Uani 1 1 d . . . . .
C8 C -0.1872(10) 0.2626(6) 0.2439(3) 0.0349(13) Uani 1 1 d . . . . .
H8 H -0.2787 0.3053 0.2796 0.042 Uiso 1 1 calc R U . . .
C7 C -0.0067(9) 0.1828(5) 0.2623(3) 0.0305(12) Uani 1 1 d . . . . .
C3 C -0.1946(9) 0.1716(5) 0.5600(3) 0.0312(12) Uani 1 1 d . . . . .
H3A H -0.3662 0.1038 0.5705 0.037 Uiso 1 1 calc R U . . .
H3B H -0.0626 0.1195 0.5757 0.037 Uiso 1 1 calc R U . . .
C4 C -0.1847(9) 0.1771(5) 0.4807(3) 0.0298(12) Uani 1 1 d . . . . .
H4A H -0.3256 0.2210 0.4640 0.036 Uiso 1 1 calc R U . . .
H4B H -0.2148 0.0665 0.4573 0.036 Uiso 1 1 calc R U . . .
C5 C 0.0727(9) 0.2791(5) 0.4592(3) 0.0277(11) Uani 1 1 d . . . . .
H5A H 0.1184 0.3825 0.4897 0.033 Uiso 1 1 calc R U . . .
H5B H 0.2082 0.2238 0.4680 0.033 Uiso 1 1 calc R U . . .
C10 C -0.1046(11) 0.2183(6) 0.1222(3) 0.0402(14) Uani 1 1 d . . . . .
C6 C 0.0444(10) 0.1641(5) 0.3387(3) 0.0336(13) Uani 1 1 d . . . . .
H6A H -0.1008 0.0797 0.3540 0.040 Uiso 1 1 calc R U . . .
H6B H 0.2037 0.1278 0.3432 0.040 Uiso 1 1 calc R U . . .
C9 C -0.2342(11) 0.2804(6) 0.1744(3) 0.0422(14) Uani 1 1 d . . . . .
H9 H -0.3571 0.3359 0.1623 0.051 Uiso 1 1 calc R U . . .
C14 C -0.0888(9) 0.3250(6) 0.6747(3) 0.0320(12) Uani 1 1 d . . . . .
H14A H -0.0182 0.4372 0.6960 0.038 Uiso 1 1 calc R U . . .
H14B H 0.0515 0.2710 0.6780 0.038 Uiso 1 1 calc R U . . .
C11 C 0.0723(11) 0.1368(7) 0.1405(3) 0.0448(15) Uani 1 1 d . . . . .
H11 H 0.1608 0.0917 0.1048 0.054 Uiso 1 1 calc R U . . .
C12 C 0.1204(10) 0.1211(6) 0.2099(3) 0.0381(13) Uani 1 1 d . . . . .
H12 H 0.2444 0.0662 0.2219 0.046 Uiso 1 1 calc R U . . .
C16 C -0.4186(13) 0.2117(8) 0.8374(3) 0.0559(18) Uani 1 1 d . . . . .
H16A H -0.3287 0.1851 0.8787 0.067 Uiso 1 1 calc R U . . .
H16B H -0.5407 0.1118 0.8151 0.067 Uiso 1 1 calc R U . . .
C13 C -0.1533(16) 0.2395(9) 0.0490(4) 0.0647(19) Uani 1 1 d . . . . .
C17 C -0.5630(13) 0.3298(8) 0.8609(4) 0.067(2) Uani 1 1 d . . . . .
H17A H -0.4402 0.4325 0.8781 0.100 Uiso 1 1 calc R U . . .
H17B H -0.6740 0.2902 0.8989 0.100 Uiso 1 1 calc R U . . .
H17C H -0.6701 0.3449 0.8210 0.100 Uiso 1 1 calc R U . . .
F1 F -0.3307(15) 0.2970(11) 0.0338(2) 0.186(4) Uani 1 1 d . . . . .
F2 F 0.0344(14) 0.3268(14) 0.0207(4) 0.226(5) Uani 1 1 d . . . . .
F3 F -0.187(3) 0.1151(10) 0.0060(3) 0.251(6) Uani 1 1 d . . . . .
C1 C 0.3173(9) 0.4279(5) 0.3714(3) 0.0300(12) Uani 1 1 d . . . . .
H1A H 0.3193 0.4379 0.3201 0.036 Uiso 1 1 calc R U . . .
H1B H 0.4640 0.3848 0.3841 0.036 Uiso 1 1 calc R U . . .
C2 C 0.3594(9) 0.5945(5) 0.4109(3) 0.0296(12) Uani 1 1 d . . . . .
H2A H 0.3787 0.5863 0.4622 0.036 Uiso 1 1 calc R U . . .
H2B H 0.5237 0.6645 0.3967 0.036 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
N1 C5 1.455(6) . ?
N1 C6 1.462(6) . ?
N1 C1 1.471(6) . ?
N2 C14 1.438(6) . ?
N2 C3 1.464(6) . ?
N2 C2 1.472(6) 2_566 ?
O2 C15 1.328(6) . ?
O2 C16 1.451(7) . ?
O1 C15 1.209(6) . ?
C15 C14 1.503(7) . ?
C8 C9 1.373(7) . ?
C8 C7 1.387(7) . ?
C8 H8 0.9500 . ?
C7 C12 1.369(7) . ?
C7 C6 1.507(7) . ?
C3 C4 1.519(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.520(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C10 C9 1.375(8) . ?
C10 C11 1.381(8) . ?
C10 C13 1.451(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C9 H9 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C11 C12 1.367(8) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C16 C17 1.483(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C13 F1 1.226(8) . ?
C13 F2 1.258(9) . ?
C13 F3 1.262(9) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C1 C2 1.525(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N2 1.472(6) 2_566 ?
C2 H2A 0.9900 . ?
C2 H2B 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
C5 N1 C6 110.6(3) . . ?
C5 N1 C1 111.1(4) . . ?
C6 N1 C1 108.9(4) . . ?
C14 N2 C3 113.0(4) . . ?
C14 N2 C2 113.2(4) . 2_566 ?
C3 N2 C2 112.6(4) . 2_566 ?
C15 O2 C16 117.4(5) . . ?
O1 C15 O2 123.4(5) . . ?
O1 C15 C14 125.9(5) . . ?
O2 C15 C14 110.7(4) . . ?
C9 C8 C7 120.3(5) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C12 C7 C8 118.7(5) . . ?
C12 C7 C6 121.3(5) . . ?
C8 C7 C6 120.0(4) . . ?
N2 C3 C4 114.6(3) . . ?
N2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
N2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 C5 112.6(4) . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C4 114.3(4) . . ?
N1 C5 H5A 108.7 . . ?
C4 C5 H5A 108.7 . . ?
N1 C5 H5B 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C9 C10 C11 119.1(5) . . ?
C9 C10 C13 120.0(6) . . ?
C11 C10 C13 120.8(6) . . ?
N1 C6 C7 113.4(4) . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C9 C10 120.5(5) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
N2 C14 C15 117.9(4) . . ?
N2 C14 H14A 107.8 . . ?
C15 C14 H14A 107.8 . . ?
N2 C14 H14B 107.8 . . ?
C15 C14 H14B 107.8 . . ?
H14A C14 H14B 107.2 . . ?
C12 C11 C10 120.1(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C7 121.3(5) . . ?
C11 C12 H12 119.4 . . ?
C7 C12 H12 119.4 . . ?
O2 C16 C17 109.6(5) . . ?
O2 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
O2 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
F1 C13 F2 102.1(8) . . ?
F1 C13 F3 104.5(8) . . ?
F2 C13 F3 97.8(8) . . ?
F1 C13 C10 119.1(7) . . ?
F2 C13 C10 115.1(7) . . ?
F3 C13 C10 115.3(6) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C1 C2 114.6(4) . . ?
N1 C1 H1A 108.6 . . ?
C2 C1 H1A 108.6 . . ?
N1 C1 H1B 108.6 . . ?
C2 C1 H1B 108.6 . . ?
H1A C1 H1B 107.6 . . ?
N2 C2 C1 114.6(4) 2_566 . ?
N2 C2 H2A 108.6 2_566 . ?
C1 C2 H2A 108.6 . . ?
N2 C2 H2B 108.6 2_566 . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?

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
C16 O2 C15 O1 -1.3(7) . . . . ?
C16 O2 C15 C14 179.0(4) . . . . ?
C9 C8 C7 C12 -0.7(7) . . . . ?
C9 C8 C7 C6 179.9(4) . . . . ?
C14 N2 C3 C4 -163.5(4) . . . . ?
C2 N2 C3 C4 66.7(5) 2_566 . . . ?
N2 C3 C4 C5 58.3(5) . . . . ?
C6 N1 C5 C4 -66.5(5) . . . . ?
C1 N1 C5 C4 172.6(4) . . . . ?
C3 C4 C5 N1 -169.3(4) . . . . ?
C5 N1 C6 C7 168.9(4) . . . . ?
C1 N1 C6 C7 -68.8(5) . . . . ?
C12 C7 C6 N1 135.0(5) . . . . ?
C8 C7 C6 N1 -45.6(6) . . . . ?
C7 C8 C9 C10 0.5(7) . . . . ?
C11 C10 C9 C8 0.4(8) . . . . ?
C13 C10 C9 C8 -179.2(5) . . . . ?
C3 N2 C14 C15 -72.2(5) . . . . ?
C2 N2 C14 C15 57.3(5) 2_566 . . . ?
O1 C15 C14 N2 12.7(7) . . . . ?
O2 C15 C14 N2 -167.6(4) . . . . ?
C9 C10 C11 C12 -1.1(8) . . . . ?
C13 C10 C11 C12 178.5(5) . . . . ?
C10 C11 C12 C7 0.9(8) . . . . ?
C8 C7 C12 C11 0.0(7) . . . . ?
C6 C7 C12 C11 179.4(5) . . . . ?
C15 O2 C16 C17 -93.9(6) . . . . ?
C9 C10 C13 F1 -8.1(10) . . . . ?
C11 C10 C13 F1 172.2(7) . . . . ?
C9 C10 C13 F2 113.6(9) . . . . ?
C11 C10 C13 F2 -66.1(10) . . . . ?
C9 C10 C13 F3 -133.6(10) . . . . ?
C11 C10 C13 F3 46.8(12) . . . . ?
C5 N1 C1 C2 -64.5(5) . . . . ?
C6 N1 C1 C2 173.5(4) . . . . ?
N1 C1 C2 N2 -56.5(5) . . . 2_566 ?

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
C3 H3A O1 0.99 2.60 3.153(6) 115.3 .
C6 H6A O1 0.99 2.61 3.441(6) 141.1 2_456
C2 H2B O1 0.99 2.47 3.082(6) 119.3 2_566

_refine_diff_density_max         0.597
_refine_diff_density_min         -0.671
_refine_diff_density_rms         0.092



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2431110'
loop_
_audit_author_name
_audit_author_address
'Luis Alves'
;Associacao do Instituto Superior Tecnico para a Investigacao e Desenvolvimento
Portugal
;
_audit_update_record             
;
2025-03-13 deposited with the CCDC.	2026-02-10 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         'C30 H42 F6 N4 O2'
_chemical_formula_sum            'C30 H42 F6 N4 O2'
_chemical_formula_weight         604.68

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'
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'
F F 0.0171 0.0103 '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                   8.930(1)
_cell_length_b                   9.2703(9)
_cell_length_c                   9.6657(9)
_cell_angle_alpha                91.972(5)
_cell_angle_beta                 106.372(6)
_cell_angle_gamma                101.663(5)
_cell_volume                     748.30(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1633
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      25.61

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6863
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.207
_diffrn_reflns_theta_max         26.467
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3093
_reflns_number_gt                2074
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_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)+(0.0641P)²+0.3967P] 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         3093
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1671
_refine_ls_wR_factor_gt          0.1540
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
N1 N 0.6849(2) 0.2885(2) 0.0402(2) 0.0240(5) Uani 1 1 d . . . . .
O1 O 0.8938(3) 0.5690(2) 0.2073(2) 0.0385(5) Uani 1 1 d . . . . .
N2 N 0.5865(2) 0.4383(2) 0.24991(19) 0.0237(5) Uani 1 1 d . . . . .
C10 C 1.1176(3) 0.0396(3) 0.3250(3) 0.0289(6) Uani 1 1 d . . . . .
C7 C 0.9003(3) 0.1462(3) 0.1082(3) 0.0277(6) Uani 1 1 d . . . . .
C12 C 0.8902(3) -0.0053(3) 0.1140(3) 0.0293(6) Uani 1 1 d . . . . .
H12 H 0.8077 -0.0732 0.0435 0.035 Uiso 1 1 calc R U . . .
C5 C 0.5690(3) 0.3285(3) -0.0850(2) 0.0261(5) Uani 1 1 d . . . . .
H5A H 0.4919 0.3718 -0.0505 0.031 Uiso 1 1 calc R U . . .
H5B H 0.5084 0.2374 -0.1491 0.031 Uiso 1 1 calc R U . . .
C4 C 0.6448(3) 0.4378(3) -0.1727(2) 0.0289(6) Uani 1 1 d . . . . .
H4A H 0.7094 0.5277 -0.1086 0.035 Uiso 1 1 calc R U . . .
H4B H 0.7175 0.3930 -0.2125 0.035 Uiso 1 1 calc R U . . .
C8 C 1.0207(3) 0.2433(3) 0.2124(3) 0.0310(6) Uani 1 1 d . . . . .
H8 H 1.0292 0.3470 0.2098 0.037 Uiso 1 1 calc R U . . .
C11 C 0.9986(3) -0.0582(3) 0.2213(3) 0.0296(6) Uani 1 1 d . . . . .
H11 H 0.9911 -0.1617 0.2235 0.035 Uiso 1 1 calc R U . . .
C2 C 0.5070(3) 0.2850(3) 0.2009(3) 0.0268(5) Uani 1 1 d . . . . .
H2A H 0.4019 0.2818 0.1297 0.032 Uiso 1 1 calc R U . . .
H2B H 0.4873 0.2342 0.2846 0.032 Uiso 1 1 calc R U . . .
C6 C 0.7841(3) 0.2019(3) -0.0114(3) 0.0313(6) Uani 1 1 d . . . . .
H6A H 0.8446 0.2645 -0.0673 0.038 Uiso 1 1 calc R U . . .
H6B H 0.7127 0.1162 -0.0780 0.038 Uiso 1 1 calc R U . . .
C1 C 0.6020(3) 0.2013(3) 0.1318(2) 0.0266(6) Uani 1 1 d . . . . .
H1A H 0.6823 0.1675 0.2095 0.032 Uiso 1 1 calc R U . . .
H1B H 0.5283 0.1122 0.0723 0.032 Uiso 1 1 calc R U . . .
F3 F 1.3064(3) -0.1046(4) 0.3914(2) 0.1119(11) Uani 1 1 d . . . . .
F1 F 1.1614(3) -0.0994(3) 0.5233(3) 0.0986(9) Uani 1 1 d . . . . .
C13 C 1.2319(3) -0.0180(3) 0.4402(3) 0.0381(7) Uani 1 1 d . . . . .
C14 C 0.7404(3) 0.4562(3) 0.3613(2) 0.0289(6) Uani 1 1 d . . . . .
H14A H 0.7832 0.3663 0.3562 0.035 Uiso 1 1 calc R U . . .
H14B H 0.7255 0.4693 0.4584 0.035 Uiso 1 1 calc R U . . .
C3 C 0.5188(3) 0.4805(3) -0.2961(2) 0.0287(6) Uani 1 1 d . . . . .
H3A H 0.5732 0.5423 -0.3569 0.034 Uiso 1 1 calc R U . . .
H3B H 0.4523 0.3895 -0.3573 0.034 Uiso 1 1 calc R U . . .
C9 C 1.1286(3) 0.1909(3) 0.3199(3) 0.0323(6) Uani 1 1 d . . . . .
H9 H 1.2107 0.2586 0.3909 0.039 Uiso 1 1 calc R U . . .
F2 F 1.3414(3) 0.0836(3) 0.5310(3) 0.0989(10) Uani 1 1 d . . . . .
C15 C 0.8571(3) 0.5888(3) 0.3396(3) 0.0340(6) Uani 1 1 d . . . . .
H15A H 0.8110 0.6774 0.3394 0.041 Uiso 1 1 calc R U . . .
H15B H 0.9568 0.6060 0.4213 0.041 Uiso 1 1 calc R U . . .
H1O H 0.823(4) 0.498(4) 0.158(4) 0.064(12) 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
N1 C5 1.467(3) . ?
N1 C1 1.470(3) . ?
N1 C6 1.479(3) . ?
O1 C15 1.422(3) . ?
O1 H1O 0.84(4) . ?
N2 C2 1.451(3) . ?
N2 C14 1.461(3) . ?
N2 C3 1.466(3) 2_665 ?
C10 C11 1.380(4) . ?
C10 C9 1.390(4) . ?
C10 C13 1.479(4) . ?
C7 C8 1.384(4) . ?
C7 C12 1.393(3) . ?
C7 C6 1.504(3) . ?
C12 C11 1.383(3) . ?
C12 H12 0.9500 . ?
C5 C4 1.519(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 C3 1.518(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C8 C9 1.380(4) . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C2 C1 1.523(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
F3 C13 1.295(3) . ?
F1 C13 1.321(3) . ?
C13 F2 1.304(3) . ?
C14 C15 1.505(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C3 N2 1.466(3) 2_665 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C9 H9 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 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
C5 N1 C1 110.61(19) . . ?
C5 N1 C6 109.26(17) . . ?
C1 N1 C6 109.82(18) . . ?
C15 O1 H1O 106(2) . . ?
C2 N2 C14 113.59(18) . . ?
C2 N2 C3 111.4(2) . 2_665 ?
C14 N2 C3 111.38(18) . 2_665 ?
C11 C10 C9 119.6(2) . . ?
C11 C10 C13 119.6(2) . . ?
C9 C10 C13 120.8(2) . . ?
C8 C7 C12 118.8(2) . . ?
C8 C7 C6 121.1(2) . . ?
C12 C7 C6 120.1(2) . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
N1 C5 C4 113.8(2) . . ?
N1 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
N1 C5 H5B 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C3 C4 C5 111.3(2) . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
N2 C2 C1 113.6(2) . . ?
N2 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
N2 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N1 C6 C7 113.84(19) . . ?
N1 C6 H6A 108.8 . . ?
C7 C6 H6A 108.8 . . ?
N1 C6 H6B 108.8 . . ?
C7 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
N1 C1 C2 114.12(18) . . ?
N1 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
F3 C13 F2 106.6(3) . . ?
F3 C13 F1 104.1(3) . . ?
F2 C13 F1 104.1(3) . . ?
F3 C13 C10 113.7(2) . . ?
F2 C13 C10 114.7(2) . . ?
F1 C13 C10 112.6(2) . . ?
N2 C14 C15 110.04(19) . . ?
N2 C14 H14A 109.7 . . ?
C15 C14 H14A 109.7 . . ?
N2 C14 H14B 109.7 . . ?
C15 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
N2 C3 C4 114.44(18) 2_665 . ?
N2 C3 H3A 108.7 2_665 . ?
C4 C3 H3A 108.7 . . ?
N2 C3 H3B 108.7 2_665 . ?
C4 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C8 C9 C10 120.3(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
O1 C15 C14 111.7(2) . . ?
O1 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
O1 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?

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
C8 C7 C12 C11 -0.3(4) . . . . ?
C6 C7 C12 C11 178.4(2) . . . . ?
C1 N1 C5 C4 171.32(19) . . . . ?
C6 N1 C5 C4 -67.7(3) . . . . ?
N1 C5 C4 C3 -177.23(19) . . . . ?
C12 C7 C8 C9 0.0(4) . . . . ?
C6 C7 C8 C9 -178.7(2) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C13 C10 C11 C12 179.3(2) . . . . ?
C7 C12 C11 C10 0.7(4) . . . . ?
C14 N2 C2 C1 -61.4(3) . . . . ?
C3 N2 C2 C1 171.81(18) 2_665 . . . ?
C5 N1 C6 C7 -176.2(2) . . . . ?
C1 N1 C6 C7 -54.7(3) . . . . ?
C8 C7 C6 N1 -62.4(3) . . . . ?
C12 C7 C6 N1 118.9(3) . . . . ?
C5 N1 C1 C2 -64.1(3) . . . . ?
C6 N1 C1 C2 175.2(2) . . . . ?
N2 C2 C1 N1 -39.2(3) . . . . ?
C11 C10 C13 F3 55.7(4) . . . . ?
C9 C10 C13 F3 -124.3(3) . . . . ?
C11 C10 C13 F2 178.7(3) . . . . ?
C9 C10 C13 F2 -1.3(4) . . . . ?
C11 C10 C13 F1 -62.4(3) . . . . ?
C9 C10 C13 F1 117.6(3) . . . . ?
C2 N2 C14 C15 143.2(2) . . . . ?
C3 N2 C14 C15 -90.0(2) 2_665 . . . ?
C5 C4 C3 N2 64.8(3) . . . 2_665 ?
C7 C8 C9 C10 0.0(4) . . . . ?
C11 C10 C9 C8 0.3(4) . . . . ?
C13 C10 C9 C8 -179.7(2) . . . . ?
N2 C14 C15 O1 -64.9(3) . . . . ?

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
O1 H1O N1 0.84(4) 2.16(4) 2.984(3) 167(3) .
O1 H1O N2 0.84(4) 2.48(4) 2.914(3) 113(3) .

_refine_diff_density_max         0.616
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.057



