# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_SPSA247122LTCuX820240507_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2410894'
loop_
_audit_author_name
_audit_author_address
'Hannah Haeusler'
;Currenta GmbH and Co OHG
Germany
;
_audit_update_record             
;
2024-12-17 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 F2 N2 O6'
_chemical_formula_sum            'C17 H16 F2 N2 O6'
_chemical_formula_weight         382.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.7401(5)
_cell_length_b                   15.6633(10)
_cell_length_c                   16.0978(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1699.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    110
_cell_measurement_reflns_used    7160
_cell_measurement_theta_min      3.94
_cell_measurement_theta_max      64.10

_exptl_crystal_description       Block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   0.8
_exptl_transmission_factor_max   0.92
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.107
_shelx_estimated_absorpt_T_min   0.471
_shelx_estimated_absorpt_T_max   0.874
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus source tube IuS'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            11024
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         5.496
_diffrn_reflns_theta_max         64.258
_diffrn_reflns_theta_full        64.258
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             2785
_reflns_number_gt                2594
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_max     0.975
_reflns_Friedel_fraction_full    0.975

_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 (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)+(0.0345P)²+0.1811P] 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_abs_structure_details 
;
 Flack x determined using 1029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2785
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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
F1 F 1.2192(2) 0.20341(11) 0.82842(12) 0.0463(5) Uani 1 1 d . . . . .
F2 F 0.6405(3) 0.15789(10) 0.98280(11) 0.0433(4) Uani 1 1 d . . . . .
O1 O 0.6710(2) 0.53356(11) 0.74953(10) 0.0218(4) Uani 1 1 d . . . . .
O2 O 0.4505(2) 0.46277(11) 0.91034(10) 0.0227(4) Uani 1 1 d . . . . .
H2A H 0.538754 0.498486 0.922604 0.034 Uiso 1 1 calc R U . . .
O3 O 0.2173(2) 0.44065(13) 0.68091(11) 0.0321(5) Uani 1 1 d . . . . .
O4 O 0.7030(2) 0.44093(11) 0.43777(10) 0.0248(4) Uani 1 1 d . . . . .
O5 O 0.8813(3) 0.30307(12) 0.59765(13) 0.0398(5) Uani 1 1 d . . . . .
O6 O 0.9218(2) 0.44241(11) 0.57260(11) 0.0259(4) Uani 1 1 d . . . . .
H6A H 1.004610 0.438482 0.611420 0.039 Uiso 1 1 calc R U . . .
N1 N 0.7880(3) 0.46087(13) 0.76909(12) 0.0209(4) Uani 1 1 d . . . . .
N2 N 0.4884(3) 0.49055(13) 0.61282(12) 0.0223(5) Uani 1 1 d . . . . .
H2B H 0.600187 0.519143 0.617693 0.027 Uiso 1 1 calc R U . . .
C1 C 1.0325(4) 0.22763(17) 0.84948(18) 0.0302(6) Uani 1 1 d . . . . .
C2 C 0.9571(4) 0.30117(16) 0.81585(16) 0.0254(6) Uani 1 1 d . . . . .
H2C H 1.032386 0.333901 0.777444 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7669(4) 0.32676(15) 0.83949(15) 0.0209(5) Uani 1 1 d . . . . .
C4 C 0.6588(4) 0.27737(16) 0.89591(15) 0.0248(6) Uani 1 1 d . . . . .
H4A H 0.529047 0.293802 0.912572 0.030 Uiso 1 1 calc R U . . .
C5 C 0.7451(4) 0.20441(17) 0.92663(17) 0.0287(6) Uani 1 1 d . . . . .
C6 C 0.9302(4) 0.17689(17) 0.90510(18) 0.0319(7) Uani 1 1 d . . . . .
H6B H 0.985523 0.125871 0.927072 0.038 Uiso 1 1 calc R U . . .
C7 C 0.6816(3) 0.40682(15) 0.80873(14) 0.0193(5) Uani 1 1 d . . . . .
C8 C 0.4646(3) 0.51120(16) 0.76241(15) 0.0222(5) Uani 1 1 d . . . . .
C9 C 0.4725(3) 0.43799(15) 0.82648(15) 0.0208(5) Uani 1 1 d . . . . .
H9A H 0.373565 0.392795 0.812015 0.025 Uiso 1 1 calc R U . . .
C10 C 0.3478(4) 0.58812(18) 0.78918(15) 0.0294(6) Uani 1 1 d . . . . .
H10A H 0.207695 0.582448 0.792762 0.035 Uiso 1 1 calc R U . . .
C11 C 0.4242(5) 0.6618(2) 0.80779(18) 0.0421(8) Uani 1 1 d . . . . .
H11A H 0.563724 0.669915 0.804941 0.051 Uiso 1 1 calc R U . . .
H11B H 0.340579 0.707616 0.824258 0.051 Uiso 1 1 calc R U . . .
C12 C 0.3800(3) 0.47679(17) 0.68044(16) 0.0225(5) Uani 1 1 d . . . . .
C13 C 0.4292(3) 0.46007(17) 0.53060(15) 0.0239(6) Uani 1 1 d . . . . .
H13A H 0.285037 0.471438 0.521035 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5534(3) 0.50149(17) 0.46230(16) 0.0244(6) Uani 1 1 d . . . . .
H14A H 0.468456 0.516318 0.414250 0.029 Uiso 1 1 calc R U . . .
H14B H 0.616290 0.554402 0.483235 0.029 Uiso 1 1 calc R U . . .
C15 C 0.6894(4) 0.36633(16) 0.48826(15) 0.0247(6) Uani 1 1 d . . . . .
H15A H 0.712391 0.314898 0.452733 0.030 Uiso 1 1 calc R U . . .
C16 C 0.4738(4) 0.36552(17) 0.51903(17) 0.0274(6) Uani 1 1 d . . . . .
H16A H 0.384213 0.339532 0.477372 0.033 Uiso 1 1 calc R U . . .
H16B H 0.461422 0.334027 0.572097 0.033 Uiso 1 1 calc R U . . .
C17 C 0.8405(4) 0.36653(17) 0.55878(15) 0.0245(6) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.357(3) . ?
F2 C5 1.358(3) . ?
O1 N1 1.420(3) . ?
O1 C8 1.450(3) . ?
O2 C9 1.412(3) . ?
O2 H2A 0.8400 . ?
O3 C12 1.234(3) . ?
O4 C15 1.426(3) . ?
O4 C14 1.439(3) . ?
O5 C17 1.206(3) . ?
O6 C17 1.328(3) . ?
O6 H6A 0.8400 . ?
N1 C7 1.280(3) . ?
N2 C12 1.329(3) . ?
N2 C13 1.462(3) . ?
N2 H2B 0.8800 . ?
C1 C2 1.370(4) . ?
C1 C6 1.381(4) . ?
C2 C3 1.396(4) . ?
C2 H2C 0.9500 . ?
C3 C4 1.398(4) . ?
C3 C7 1.466(4) . ?
C4 C5 1.374(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.365(4) . ?
C6 H6B 0.9500 . ?
C7 C9 1.518(3) . ?
C8 C10 1.502(4) . ?
C8 C12 1.535(4) . ?
C8 C9 1.543(3) . ?
C9 H9A 1.0000 . ?
C10 C11 1.299(4) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
C13 C16 1.523(4) . ?
C13 C14 1.527(3) . ?
C13 H13A 1.0000 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C17 1.525(4) . ?
C15 C16 1.535(3) . ?
C15 H15A 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 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
N1 O1 C8 107.91(16) . . ?
C9 O2 H2A 109.5 . . ?
C15 O4 C14 109.81(18) . . ?
C17 O6 H6A 109.5 . . ?
C7 N1 O1 109.23(17) . . ?
C12 N2 C13 122.6(2) . . ?
C12 N2 H2B 118.7 . . ?
C13 N2 H2B 118.7 . . ?
F1 C1 C2 118.7(3) . . ?
F1 C1 C6 117.6(2) . . ?
C2 C1 C6 123.7(2) . . ?
C1 C2 C3 118.3(2) . . ?
C1 C2 H2C 120.9 . . ?
C3 C2 H2C 120.9 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 C7 120.9(2) . . ?
C4 C3 C7 119.2(2) . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 H4A 120.9 . . ?
C3 C4 H4A 120.9 . . ?
F2 C5 C6 118.3(2) . . ?
F2 C5 C4 117.8(2) . . ?
C6 C5 C4 123.9(3) . . ?
C5 C6 C1 116.0(3) . . ?
C5 C6 H6B 122.0 . . ?
C1 C6 H6B 122.0 . . ?
N1 C7 C3 120.9(2) . . ?
N1 C7 C9 113.7(2) . . ?
C3 C7 C9 125.1(2) . . ?
O1 C8 C10 110.5(2) . . ?
O1 C8 C12 108.55(19) . . ?
C10 C8 C12 109.5(2) . . ?
O1 C8 C9 104.00(18) . . ?
C10 C8 C9 115.0(2) . . ?
C12 C8 C9 109.1(2) . . ?
O2 C9 C7 111.44(19) . . ?
O2 C9 C8 115.5(2) . . ?
C7 C9 C8 98.35(18) . . ?
O2 C9 H9A 110.3 . . ?
C7 C9 H9A 110.3 . . ?
C8 C9 H9A 110.3 . . ?
C11 C10 C8 124.8(3) . . ?
C11 C10 H10A 117.6 . . ?
C8 C10 H10A 117.6 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
O3 C12 N2 124.6(2) . . ?
O3 C12 C8 119.1(2) . . ?
N2 C12 C8 116.3(2) . . ?
N2 C13 C16 112.0(2) . . ?
N2 C13 C14 111.32(19) . . ?
C16 C13 C14 102.5(2) . . ?
N2 C13 H13A 110.3 . . ?
C16 C13 H13A 110.3 . . ?
C14 C13 H13A 110.3 . . ?
O4 C14 C13 107.5(2) . . ?
O4 C14 H14A 110.2 . . ?
C13 C14 H14A 110.2 . . ?
O4 C14 H14B 110.2 . . ?
C13 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
O4 C15 C17 112.3(2) . . ?
O4 C15 C16 104.5(2) . . ?
C17 C15 C16 113.1(2) . . ?
O4 C15 H15A 108.9 . . ?
C17 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C13 C16 C15 102.6(2) . . ?
C13 C16 H16A 111.2 . . ?
C15 C16 H16A 111.2 . . ?
C13 C16 H16B 111.2 . . ?
C15 C16 H16B 111.2 . . ?
H16A C16 H16B 109.2 . . ?
O5 C17 O6 123.8(2) . . ?
O5 C17 C15 122.5(2) . . ?
O6 C17 C15 113.7(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
C8 O1 N1 C7 -14.4(2) . . . . ?
F1 C1 C2 C3 -178.4(2) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C7 177.2(2) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C7 C3 C4 C5 -177.3(2) . . . . ?
C3 C4 C5 F2 178.6(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
F2 C5 C6 C1 -178.3(2) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
F1 C1 C6 C5 178.3(2) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
O1 N1 C7 C3 -177.73(19) . . . . ?
O1 N1 C7 C9 -3.2(3) . . . . ?
C2 C3 C7 N1 -9.8(4) . . . . ?
C4 C3 C7 N1 167.6(2) . . . . ?
C2 C3 C7 C9 176.3(2) . . . . ?
C4 C3 C7 C9 -6.3(3) . . . . ?
N1 O1 C8 C10 148.82(18) . . . . ?
N1 O1 C8 C12 -91.1(2) . . . . ?
N1 O1 C8 C9 24.9(2) . . . . ?
N1 C7 C9 O2 -104.0(2) . . . . ?
C3 C7 C9 O2 70.3(3) . . . . ?
N1 C7 C9 C8 17.7(3) . . . . ?
C3 C7 C9 C8 -168.0(2) . . . . ?
O1 C8 C9 O2 94.4(2) . . . . ?
C10 C8 C9 O2 -26.6(3) . . . . ?
C12 C8 C9 O2 -149.98(19) . . . . ?
O1 C8 C9 C7 -24.3(2) . . . . ?
C10 C8 C9 C7 -145.2(2) . . . . ?
C12 C8 C9 C7 91.4(2) . . . . ?
O1 C8 C10 C11 -7.6(4) . . . . ?
C12 C8 C10 C11 -127.1(3) . . . . ?
C9 C8 C10 C11 109.7(3) . . . . ?
C13 N2 C12 O3 -3.0(4) . . . . ?
C13 N2 C12 C8 178.7(2) . . . . ?
O1 C8 C12 O3 167.8(2) . . . . ?
C10 C8 C12 O3 -71.5(3) . . . . ?
C9 C8 C12 O3 55.1(3) . . . . ?
O1 C8 C12 N2 -13.8(3) . . . . ?
C10 C8 C12 N2 106.9(2) . . . . ?
C9 C8 C12 N2 -126.5(2) . . . . ?
C12 N2 C13 C16 -78.9(3) . . . . ?
C12 N2 C13 C14 167.0(2) . . . . ?
C15 O4 C14 C13 -3.1(2) . . . . ?
N2 C13 C14 O4 100.6(2) . . . . ?
C16 C13 C14 O4 -19.3(2) . . . . ?
C14 O4 C15 C17 -98.8(2) . . . . ?
C14 O4 C15 C16 24.2(2) . . . . ?
N2 C13 C16 C15 -86.8(2) . . . . ?
C14 C13 C16 C15 32.6(2) . . . . ?
O4 C15 C16 C13 -35.5(2) . . . . ?
C17 C15 C16 C13 87.0(2) . . . . ?
O4 C15 C17 O5 -164.5(2) . . . . ?
C16 C15 C17 O5 77.5(3) . . . . ?
O4 C15 C17 O6 15.2(3) . . . . ?
C16 C15 C17 O6 -102.8(3) . . . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_SPSA2114211LTCuX820230825_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2410895'
loop_
_audit_author_name
_audit_author_address
'Hannah Haeusler'
;Currenta GmbH and Co OHG
Germany
;
_audit_update_record             
;
2024-12-17 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 F2 N O4'
_chemical_formula_sum            'C13 H11 F2 N O4'
_chemical_formula_weight         283.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   5.8796(8)
_cell_length_b                   6.5729(9)
_cell_length_c                   8.5183(11)
_cell_angle_alpha                84.671(5)
_cell_angle_beta                 79.616(7)
_cell_angle_gamma                73.035(5)
_cell_volume                     309.43(7)
_cell_formula_units_Z            1
_cell_measurement_temperature    110
_cell_measurement_reflns_used    7633
_cell_measurement_theta_min      5.2840
_cell_measurement_theta_max      63.6947

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             146
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.151
_shelx_estimated_absorpt_T_min   0.724
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      110
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            6636
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.284
_diffrn_reflns_theta_max         63.867
_diffrn_reflns_theta_full        63.867
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.923
_reflns_number_total             1886
_reflns_number_gt                1846
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.880
_reflns_Friedel_fraction_max     0.864
_reflns_Friedel_fraction_full    0.864

_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 (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)+(0.0424P)²+0.0331P] 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_abs_structure_details 
;
 Flack x determined using 847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1886
_refine_ls_number_parameters     183
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0687
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_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
F1 F 1.2499(3) 0.1998(3) 0.06164(19) 0.0383(4) Uani 1 1 d . . . . .
F2 F 0.6150(3) -0.1075(2) 0.22108(18) 0.0350(4) Uani 1 1 d . . . . .
O1 O 0.5859(3) 0.7796(3) 0.6323(2) 0.0242(4) Uani 1 1 d . . . . .
O2 O 0.2034(3) 0.6871(3) 0.4417(2) 0.0250(4) Uani 1 1 d . . . . .
H2A H 0.065828 0.668223 0.465219 0.038 Uiso 1 1 calc R U . . .
O3 O 0.1888(3) 1.1082(3) 0.6407(2) 0.0313(4) Uani 1 1 d . . . . .
O4 O -0.0459(3) 0.9059(3) 0.76302(19) 0.0221(4) Uani 1 1 d . . . . .
N1 N 0.7304(4) 0.6308(3) 0.5216(2) 0.0227(4) Uani 1 1 d . . . . .
C1 C 1.0395(4) 0.1980(4) 0.1577(3) 0.0267(6) Uani 1 1 d . . . . .
C2 C 0.9396(5) 0.0371(4) 0.1417(3) 0.0290(6) Uani 1 1 d . . . . .
H2B H 1.016805 -0.073016 0.069088 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7220(5) 0.0450(4) 0.2364(3) 0.0256(5) Uani 1 1 d . . . . .
C4 C 0.6063(4) 0.1998(4) 0.3457(3) 0.0235(5) Uani 1 1 d . . . . .
H4 H 0.455609 0.199811 0.408835 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7178(4) 0.3562(4) 0.3602(3) 0.0208(5) Uani 1 1 d . . . . .
C6 C 0.9374(4) 0.3566(4) 0.2632(3) 0.0248(5) Uani 1 1 d . . . . .
H6 H 1.013118 0.464009 0.270589 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6072(4) 0.5186(4) 0.4797(3) 0.0205(5) Uani 1 1 d . . . . .
C8 C 0.3451(4) 0.5820(4) 0.5582(3) 0.0203(5) Uani 1 1 d . . . . .
H8 H 0.293598 0.455717 0.608920 0.024 Uiso 1 1 calc R U . . .
C9 C 0.3613(4) 0.7287(4) 0.6851(3) 0.0211(5) Uani 1 1 d . . . . .
C10 C 0.3617(5) 0.6183(4) 0.8492(3) 0.0253(6) Uani 1 1 d . . . . .
H10A H 0.232334 0.559418 0.890664 0.030 Uiso 1 1 calc R U . . .
C11 C 0.5293(5) 0.5981(4) 0.9389(3) 0.0326(6) Uani 1 1 d . . . . .
H11A H 0.661318 0.655074 0.901297 0.039 Uiso 1 1 calc R U . . .
H11B H 0.517768 0.526687 1.040988 0.039 Uiso 1 1 calc R U . . .
C12 C 0.1618(4) 0.9388(4) 0.6904(3) 0.0210(5) Uani 1 1 d . . . . .
C13 C -0.2503(4) 1.0953(4) 0.7810(3) 0.0245(5) Uani 1 1 d . . . . .
H13C H -0.201983 1.210514 0.818667 0.037 Uiso 1 1 calc R U . . .
H13B H -0.381723 1.064151 0.858701 0.037 Uiso 1 1 calc R U . . .
H13A H -0.304806 1.138961 0.677702 0.037 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
F1 C1 1.357(3) . ?
F2 C3 1.356(3) . ?
O1 N1 1.402(3) . ?
O1 C9 1.440(3) . ?
O2 C8 1.411(3) . ?
O2 H2A 0.8400 . ?
O3 C12 1.198(3) . ?
O4 C12 1.334(3) . ?
O4 C13 1.454(3) . ?
N1 C7 1.284(3) . ?
C1 C6 1.367(4) . ?
C1 C2 1.378(4) . ?
C2 C3 1.374(4) . ?
C2 H2B 0.9500 . ?
C3 C4 1.381(4) . ?
C4 C5 1.396(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.403(3) . ?
C5 C7 1.469(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.517(3) . ?
C8 C9 1.547(4) . ?
C8 H8 1.0000 . ?
C9 C10 1.514(3) . ?
C9 C12 1.528(3) . ?
C10 C11 1.323(4) . ?
C10 H10A 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
C13 H13C 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13A 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C9 108.56(17) . . ?
C8 O2 H2A 109.5 . . ?
C12 O4 C13 115.19(17) . . ?
C7 N1 O1 110.51(18) . . ?
F1 C1 C6 118.3(2) . . ?
F1 C1 C2 117.9(2) . . ?
C6 C1 C2 123.8(2) . . ?
C3 C2 C1 116.3(2) . . ?
C3 C2 H2B 121.9 . . ?
C1 C2 H2B 121.9 . . ?
F2 C3 C2 118.0(2) . . ?
F2 C3 C4 118.3(2) . . ?
C2 C3 C4 123.6(2) . . ?
C3 C4 C5 117.9(2) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 C7 119.9(2) . . ?
C6 C5 C7 119.8(2) . . ?
C1 C6 C5 118.1(2) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
N1 C7 C5 120.6(2) . . ?
N1 C7 C8 113.2(2) . . ?
C5 C7 C8 126.1(2) . . ?
O2 C8 C7 108.42(17) . . ?
O2 C8 C9 114.35(18) . . ?
C7 C8 C9 99.02(19) . . ?
O2 C8 H8 111.5 . . ?
C7 C8 H8 111.5 . . ?
C9 C8 H8 111.5 . . ?
O1 C9 C10 109.89(19) . . ?
O1 C9 C12 106.89(18) . . ?
C10 C9 C12 110.5(2) . . ?
O1 C9 C8 105.27(19) . . ?
C10 C9 C8 111.80(19) . . ?
C12 C9 C8 112.18(19) . . ?
C11 C10 C9 124.6(2) . . ?
C11 C10 H10A 117.7 . . ?
C9 C10 H10A 117.7 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
O3 C12 O4 125.2(2) . . ?
O3 C12 C9 125.3(2) . . ?
O4 C12 C9 109.52(19) . . ?
O4 C13 H13C 109.5 . . ?
O4 C13 H13B 109.5 . . ?
H13C C13 H13B 109.5 . . ?
O4 C13 H13A 109.5 . . ?
H13C C13 H13A 109.5 . . ?
H13B C13 H13A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 N1 C7 11.1(2) . . . . ?
F1 C1 C2 C3 -177.6(2) . . . . ?
C6 C1 C2 C3 1.6(4) . . . . ?
C1 C2 C3 F2 178.3(2) . . . . ?
C1 C2 C3 C4 -1.4(3) . . . . ?
F2 C3 C4 C5 -179.9(2) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
C3 C4 C5 C7 -177.3(2) . . . . ?
F1 C1 C6 C5 178.9(2) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C7 C5 C6 C1 177.5(2) . . . . ?
O1 N1 C7 C5 177.97(19) . . . . ?
O1 N1 C7 C8 1.2(2) . . . . ?
C4 C5 C7 N1 163.4(2) . . . . ?
C6 C5 C7 N1 -15.5(3) . . . . ?
C4 C5 C7 C8 -20.3(3) . . . . ?
C6 C5 C7 C8 160.8(2) . . . . ?
N1 C7 C8 O2 107.8(2) . . . . ?
C5 C7 C8 O2 -68.7(3) . . . . ?
N1 C7 C8 C9 -11.7(2) . . . . ?
C5 C7 C8 C9 171.7(2) . . . . ?
N1 O1 C9 C10 102.4(2) . . . . ?
N1 O1 C9 C12 -137.57(19) . . . . ?
N1 O1 C9 C8 -18.1(2) . . . . ?
O2 C8 C9 O1 -97.9(2) . . . . ?
C7 C8 C9 O1 17.1(2) . . . . ?
O2 C8 C9 C10 142.8(2) . . . . ?
C7 C8 C9 C10 -102.1(2) . . . . ?
O2 C8 C9 C12 18.0(3) . . . . ?
C7 C8 C9 C12 133.03(19) . . . . ?
O1 C9 C10 C11 8.4(3) . . . . ?
C12 C9 C10 C11 -109.3(3) . . . . ?
C8 C9 C10 C11 124.9(3) . . . . ?
C13 O4 C12 O3 -0.2(3) . . . . ?
C13 O4 C12 C9 178.00(19) . . . . ?
O1 C9 C12 O3 8.3(3) . . . . ?
C10 C9 C12 O3 127.9(3) . . . . ?
C8 C9 C12 O3 -106.6(3) . . . . ?
O1 C9 C12 O4 -169.89(18) . . . . ?
C10 C9 C12 O4 -50.3(3) . . . . ?
C8 C9 C12 O4 75.2(2) . . . . ?

_refine_diff_density_max         0.142
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.045

