# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1846439'
_audit_update_record             
;
2018-05-31 deposited with the CCDC.	2019-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 F5 N3 O4'
_chemical_formula_weight         467.35

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.2387(14)
_cell_length_b                   9.1226(15)
_cell_length_c                   15.647(3)
_cell_angle_alpha                78.884(2)
_cell_angle_beta                 77.335(2)
_cell_angle_gamma                63.875(2)
_cell_volume                     1023.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3188
_cell_measurement_theta_min      2.0
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            pink
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7987
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.502
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             3571
_reflns_number_gt                2672
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0856P)²+0.2544P] 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     SHELXL
_refine_ls_extinction_coef       0.023(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3571
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1619
_refine_ls_wR_factor_gt          0.1497
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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 0.7472(3) 0.7305(3) 0.75253(12) 0.0955(6) Uani 1 1 d . . . . .
F2 F 1.0110(3) -0.1945(2) 0.06244(13) 0.1017(7) Uani 1 1 d . . . . .
F3 F 0.6202(4) 0.8520(2) 0.30890(18) 0.1369(11) Uani 1 1 d . . . . .
F4 F 0.3768(3) 0.8276(3) 0.3195(2) 0.1541(13) Uani 1 1 d . . . . .
F5 F 0.5415(3) 0.8224(2) 0.19780(12) 0.0976(6) Uani 1 1 d . . . . .
N1 N 0.8182(3) 0.3552(2) 0.49751(13) 0.0635(6) Uani 1 1 d . . . . .
H1 H 0.8688 0.2517 0.5144 0.076 Uiso 1 1 calc R U . . .
N2 N 0.6849(2) 0.5512(2) 0.38533(12) 0.0491(5) Uani 1 1 d . . . . .
N3 N 0.9018(3) 0.0991(2) 0.39513(13) 0.0603(6) Uani 1 1 d . . . . .
O1 O 1.0560(3) 0.0439(2) 0.41231(13) 0.0814(6) Uani 1 1 d . . . . .
O2 O 0.8103(4) 0.0209(3) 0.40737(17) 0.0961(8) Uani 1 1 d . . . . .
O3 O 0.4836(2) 0.5683(3) 0.13982(12) 0.0731(6) Uani 1 1 d . . . . .
O4 O 0.7776(2) 0.5192(2) 0.09213(11) 0.0608(5) Uani 1 1 d . . . . .
C1 C 0.7931(3) 0.4599(3) 0.56015(15) 0.0526(6) Uani 1 1 d . . . . .
C2 C 0.8854(4) 0.3871(4) 0.63118(18) 0.0706(8) Uani 1 1 d . . . . .
H2 H 0.9598 0.2751 0.6352 0.085 Uiso 1 1 calc R U . . .
C3 C 0.8700(4) 0.4763(4) 0.69624(19) 0.0731(8) Uani 1 1 d . . . . .
H3 H 0.9320 0.4260 0.7443 0.088 Uiso 1 1 calc R U . . .
C4 C 0.7622(4) 0.6395(4) 0.68850(18) 0.0671(7) Uani 1 1 d . . . . .
C5 C 0.6672(5) 0.7165(4) 0.6203(2) 0.0868(10) Uani 1 1 d . . . . .
H5 H 0.5940 0.8288 0.6169 0.104 Uiso 1 1 calc R U . . .
C6 C 0.6812(4) 0.6251(4) 0.5559(2) 0.0783(9) Uani 1 1 d . . . . .
H6 H 0.6145 0.6757 0.5094 0.094 Uiso 1 1 calc R U . . .
C7 C 0.7741(3) 0.3943(3) 0.41465(15) 0.0487(5) Uani 1 1 d . . . . .
C8 C 0.8185(3) 0.2728(3) 0.35891(15) 0.0484(5) Uani 1 1 d . . . . .
C9 C 0.7821(3) 0.3098(3) 0.27363(15) 0.0460(5) Uani 1 1 d . . . . .
C10 C 0.6884(3) 0.4779(3) 0.24433(14) 0.0458(5) Uani 1 1 d . . . . .
C11 C 0.6441(3) 0.5895(3) 0.30378(15) 0.0476(5) Uani 1 1 d . . . . .
C12 C 0.8426(3) 0.1783(3) 0.21505(14) 0.0462(5) Uani 1 1 d . . . . .
C13 C 1.0246(3) 0.0679(3) 0.20195(16) 0.0548(6) Uani 1 1 d . . . . .
H13 H 1.1092 0.0790 0.2280 0.066 Uiso 1 1 calc R U . . .
C14 C 1.0820(4) -0.0586(3) 0.15059(17) 0.0630(7) Uani 1 1 d . . . . .
H14 H 1.2038 -0.1339 0.1425 0.076 Uiso 1 1 calc R U . . .
C15 C 0.9557(4) -0.0700(3) 0.11224(18) 0.0663(7) Uani 1 1 d . . . . .
C16 C 0.7761(4) 0.0383(3) 0.12140(18) 0.0668(7) Uani 1 1 d . . . . .
H16 H 0.6940 0.0285 0.0929 0.080 Uiso 1 1 calc R U . . .
C17 C 0.7187(3) 0.1627(3) 0.17382(17) 0.0578(6) Uani 1 1 d . . . . .
H17 H 0.5964 0.2367 0.1816 0.069 Uiso 1 1 calc R U . . .
C18 C 0.5457(4) 0.7724(3) 0.28218(18) 0.0638(7) Uani 1 1 d . . . . .
C19 C 0.6354(3) 0.5286(3) 0.15328(15) 0.0494(6) Uani 1 1 d . . . . .
C20 C 0.7434(4) 0.5639(4) 0.00020(17) 0.0716(8) Uani 1 1 d . . . . .
H20A H 0.6521 0.5292 -0.0072 0.086 Uiso 1 1 calc R U . . .
H20B H 0.8552 0.5076 -0.0387 0.086 Uiso 1 1 calc R U . . .
C21 C 0.6788(6) 0.7425(4) -0.0237(2) 0.0979(11) Uani 1 1 d . . . . .
H21A H 0.6628 0.7687 -0.0846 0.147 Uiso 1 1 calc R U . . .
H21B H 0.7674 0.7774 -0.0145 0.147 Uiso 1 1 calc R U . . .
H21C H 0.5643 0.7979 0.0124 0.147 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 C4 1.373(3) . ?
F2 C15 1.355(3) . ?
F3 C18 1.305(3) . ?
F4 C18 1.292(3) . ?
F5 C18 1.314(3) . ?
N1 C7 1.362(3) . ?
N1 C1 1.419(3) . ?
N1 H1 0.8600 . ?
N2 C7 1.329(3) . ?
N2 C11 1.333(3) . ?
N3 O2 1.214(3) . ?
N3 O1 1.214(3) . ?
N3 C8 1.473(3) . ?
O3 C19 1.195(3) . ?
O4 C19 1.321(3) . ?
O4 C20 1.472(3) . ?
C1 C6 1.375(4) . ?
C1 C2 1.377(4) . ?
C2 C3 1.373(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.354(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(4) . ?
C5 C6 1.383(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.413(3) . ?
C8 C9 1.377(3) . ?
C9 C10 1.414(3) . ?
C9 C12 1.492(3) . ?
C10 C11 1.387(3) . ?
C10 C19 1.508(3) . ?
C11 C18 1.505(3) . ?
C12 C13 1.386(3) . ?
C12 C17 1.389(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.359(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(4) . ?
C16 C17 1.379(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C20 C21 1.472(5) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

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
C7 N1 C1 129.6(2) . . ?
C7 N1 H1 115.2 . . ?
C1 N1 H1 115.2 . . ?
C7 N2 C11 119.22(19) . . ?
O2 N3 O1 124.1(2) . . ?
O2 N3 C8 117.7(2) . . ?
O1 N3 C8 118.2(2) . . ?
C19 O4 C20 116.60(19) . . ?
C6 C1 C2 118.6(2) . . ?
C6 C1 N1 124.9(2) . . ?
C2 C1 N1 116.5(2) . . ?
C3 C2 C1 121.5(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C3 C4 C5 122.6(3) . . ?
C3 C4 F1 118.8(3) . . ?
C5 C4 F1 118.6(3) . . ?
C4 C5 C6 118.8(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 120.3(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N2 C7 N1 119.2(2) . . ?
N2 C7 C8 118.76(19) . . ?
N1 C7 C8 122.01(19) . . ?
C9 C8 C7 123.0(2) . . ?
C9 C8 N3 118.85(19) . . ?
C7 C8 N3 118.14(19) . . ?
C8 C9 C10 116.7(2) . . ?
C8 C9 C12 121.20(19) . . ?
C10 C9 C12 122.07(19) . . ?
C11 C10 C9 116.9(2) . . ?
C11 C10 C19 122.89(19) . . ?
C9 C10 C19 120.15(19) . . ?
N2 C11 C10 125.3(2) . . ?
N2 C11 C18 111.5(2) . . ?
C10 C11 C18 123.2(2) . . ?
C13 C12 C17 119.0(2) . . ?
C13 C12 C9 119.96(19) . . ?
C17 C12 C9 121.1(2) . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 118.2(2) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
F2 C15 C14 118.4(3) . . ?
F2 C15 C16 118.5(2) . . ?
C14 C15 C16 123.1(2) . . ?
C15 C16 C17 118.6(2) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C16 C17 C12 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
F4 C18 F3 106.5(3) . . ?
F4 C18 F5 105.7(3) . . ?
F3 C18 F5 105.5(2) . . ?
F4 C18 C11 111.8(2) . . ?
F3 C18 C11 111.9(2) . . ?
F5 C18 C11 114.8(2) . . ?
O3 C19 O4 125.4(2) . . ?
O3 C19 C10 123.0(2) . . ?
O4 C19 C10 111.54(18) . . ?
O4 C20 C21 110.7(2) . . ?
O4 C20 H20A 109.5 . . ?
C21 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 108.1 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C21 H21A F1 0.96 2.54 3.437(4) 155.6 1_554
C20 H20B F2 0.97 2.64 3.288(3) 124.5 2_755
C6 H6 N2 0.93 2.27 2.867(3) 121.0 .
C2 H2 O2 0.93 2.64 3.534(4) 162.0 2_756
N1 H1 O1 0.86 2.57 3.414(3) 166.1 2_756
N1 H1 O1 0.86 2.46 3.016(3) 123.3 .
C21 H21A F1 0.96 2.54 3.437(4) 155.6 1_554
C20 H20B F2 0.97 2.64 3.288(3) 124.5 2_755
C6 H6 N2 0.93 2.27 2.867(3) 121.0 .
C2 H2 O2 0.93 2.64 3.534(4) 162.0 2_756
N1 H1 O1 0.86 2.57 3.414(3) 166.1 2_756
N1 H1 O1 0.86 2.46 3.016(3) 123.3 .
C21 H21A F1 0.96 2.54 3.437(4) 155.6 1_554
C20 H20B F2 0.97 2.64 3.288(3) 124.5 2_755
C6 H6 N2 0.93 2.27 2.867(3) 121.0 .
C2 H2 O2 0.93 2.64 3.534(4) 162.0 2_756
N1 H1 O1 0.86 2.57 3.414(3) 166.1 2_756
N1 H1 O1 0.86 2.46 3.016(3) 123.3 .
N1 H1 O1 0.86 2.46 3.016(3) 123.3 .
N1 H1 O1 0.86 2.57 3.414(3) 166.1 2_756
C2 H2 O2 0.93 2.64 3.534(4) 162.0 2_756
C6 H6 N2 0.93 2.27 2.867(3) 121.0 .
C20 H20B F2 0.97 2.64 3.288(3) 124.5 2_755
C21 H21A F1 0.96 2.54 3.437(4) 155.6 1_554
N1 H1 O1 0.86 2.46 3.016(3) 123.3 .
N1 H1 O1 0.86 2.57 3.414(3) 166.1 2_756
C2 H2 O2 0.93 2.64 3.534(4) 162.0 2_756
C6 H6 N2 0.93 2.27 2.867(3) 121.0 .
C20 H20B F2 0.97 2.64 3.288(3) 124.5 2_755
C21 H21A F1 0.96 2.54 3.437(4) 155.6 1_554
N1 H1 O1 0.86 2.46 3.016(3) 123.3 .
N1 H1 O1 0.86 2.57 3.414(3) 166.1 2_756
C2 H2 O2 0.93 2.64 3.534(4) 162.0 2_756
C6 H6 N2 0.93 2.27 2.867(3) 121.0 .
C20 H20B F2 0.97 2.64 3.288(3) 124.5 2_755
C21 H21A F1 0.96 2.54 3.437(4) 155.6 1_554

_refine_diff_density_max         0.432
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.040

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1846441'
_audit_update_record             
;
2018-05-31 deposited with the CCDC.	2019-02-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 F5 N2 O2'
_chemical_formula_weight         450.40

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                   8.6308(16)
_cell_length_b                   9.4049(18)
_cell_length_c                   13.955(3)
_cell_angle_alpha                78.895(2)
_cell_angle_beta                 81.887(2)
_cell_angle_gamma                74.726(2)
_cell_volume                     1067.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2016
_cell_measurement_theta_min      2.4575
_cell_measurement_theta_max      21.6051

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.959
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8534
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.494
_diffrn_reflns_theta_max         25.150
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3809
_reflns_number_gt                2382
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0817P)²+0.3047P] 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         3809
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1386
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 0.2086(4) 1.1738(3) -0.38934(16) 0.1330(10) Uani 1 1 d . . . . .
F2 F 0.8479(2) 0.7425(3) -0.03675(13) 0.1016(8) Uani 1 1 d . . . . .
F3 F 0.9207(2) 0.8325(2) 0.07376(16) 0.0909(6) Uani 1 1 d . . . . .
F4 F 1.03416(19) 0.61130(19) 0.04922(12) 0.0711(5) Uani 1 1 d . . . . .
F5 F 0.7564(3) 0.1553(2) 0.64535(13) 0.0965(7) Uani 1 1 d . . . . .
N1 N 0.3488(3) 0.7147(3) 0.12613(17) 0.0667(7) Uani 1 1 d . . . . .
H1 H 0.2688 0.6873 0.1620 0.080 Uiso 1 1 calc R U . . .
N2 N 0.6196(3) 0.7044(2) 0.09806(15) 0.0510(6) Uani 1 1 d . . . . .
O1 O 1.0619(2) 0.5833(2) 0.25155(15) 0.0719(6) Uani 1 1 d . . . . .
O2 O 1.0221(2) 0.3569(2) 0.25038(16) 0.0686(6) Uani 1 1 d . . . . .
C1 C 0.2465(5) 1.0686(4) -0.3083(2) 0.0783(10) Uani 1 1 d . . . . .
C2 C 0.1447(5) 0.9796(4) -0.2700(3) 0.0854(10) Uani 1 1 d . . . . .
H2 H 0.0493 0.9907 -0.2975 0.102 Uiso 1 1 calc R U . . .
C3 C 0.1859(4) 0.8724(4) -0.1893(2) 0.0674(8) Uani 1 1 d . . . . .
H3 H 0.1169 0.8109 -0.1626 0.081 Uiso 1 1 calc R U . . .
C4 C 0.3257(3) 0.8539(3) -0.1473(2) 0.0556(7) Uani 1 1 d . . . . .
C5 C 0.4249(4) 0.9490(3) -0.1879(2) 0.0647(8) Uani 1 1 d . . . . .
H5 H 0.5189 0.9408 -0.1596 0.078 Uiso 1 1 calc R U . . .
C6 C 0.3863(5) 1.0559(4) -0.2699(2) 0.0774(10) Uani 1 1 d . . . . .
H6 H 0.4547 1.1175 -0.2980 0.093 Uiso 1 1 calc R U . . .
C7 C 0.3638(4) 0.7423(3) -0.0559(2) 0.0660(8) Uani 1 1 d . . . . .
H7A H 0.4782 0.6947 -0.0601 0.079 Uiso 1 1 calc R U . . .
H7B H 0.3054 0.6656 -0.0505 0.079 Uiso 1 1 calc R U . . .
C8 C 0.3177(3) 0.8169(3) 0.0349(2) 0.0611(7) Uani 1 1 d . . . . .
H8A H 0.3773 0.8929 0.0291 0.073 Uiso 1 1 calc R U . . .
H8B H 0.2038 0.8666 0.0374 0.073 Uiso 1 1 calc R U . . .
C9 C 0.4975(3) 0.6607(3) 0.15734(19) 0.0511(7) Uani 1 1 d . . . . .
C10 C 0.5240(3) 0.5663(3) 0.24767(19) 0.0536(7) Uani 1 1 d . . . . .
H10 H 0.4377 0.5377 0.2874 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6768(3) 0.5161(3) 0.27767(18) 0.0471(6) Uani 1 1 d . . . . .
C12 C 0.8063(3) 0.5614(3) 0.21565(18) 0.0455(6) Uani 1 1 d . . . . .
C13 C 0.7672(3) 0.6539(3) 0.12771(18) 0.0471(6) Uani 1 1 d . . . . .
C14 C 0.8917(3) 0.7102(3) 0.0532(2) 0.0585(7) Uani 1 1 d . . . . .
C15 C 0.6999(3) 0.4209(3) 0.37564(18) 0.0492(6) Uani 1 1 d . . . . .
C16 C 0.6355(4) 0.2967(3) 0.4013(2) 0.0634(8) Uani 1 1 d . . . . .
H16 H 0.5790 0.2734 0.3569 0.076 Uiso 1 1 calc R U . . .
C17 C 0.6540(4) 0.2071(4) 0.4920(2) 0.0740(9) Uani 1 1 d . . . . .
H17 H 0.6103 0.1241 0.5089 0.089 Uiso 1 1 calc R U . . .
C18 C 0.7376(4) 0.2430(4) 0.5559(2) 0.0659(8) Uani 1 1 d . . . . .
C19 C 0.8022(4) 0.3641(4) 0.5345(2) 0.0668(8) Uani 1 1 d . . . . .
H19 H 0.8584 0.3862 0.5797 0.080 Uiso 1 1 calc R U . . .
C20 C 0.7822(3) 0.4534(3) 0.4439(2) 0.0588(7) Uani 1 1 d . . . . .
H20 H 0.8248 0.5371 0.4283 0.071 Uiso 1 1 calc R U . . .
C21 C 0.9761(3) 0.5063(3) 0.24151(19) 0.0541(7) Uani 1 1 d . . . . .
C22 C 1.1869(4) 0.2815(5) 0.2713(3) 0.0976(12) Uani 1 1 d . . . . .
H22A H 1.2257 0.1991 0.2347 0.117 Uiso 1 1 calc R U . . .
H22B H 1.2552 0.3508 0.2493 0.117 Uiso 1 1 calc R U . . .
C23 C 1.2000(5) 0.2255(6) 0.3734(3) 0.1224(16) Uani 1 1 d . . . . .
H23A H 1.1760 0.3077 0.4090 0.184 Uiso 1 1 calc R U . . .
H23B H 1.3078 0.1670 0.3826 0.184 Uiso 1 1 calc R U . . .
H23C H 1.1250 0.1644 0.3971 0.184 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 1.367(4) . ?
F2 C14 1.318(3) . ?
F3 C14 1.329(3) . ?
F4 C14 1.333(3) . ?
F5 C18 1.362(3) . ?
N1 C9 1.350(3) . ?
N1 C8 1.451(3) . ?
N1 H1 0.8600 . ?
N2 C13 1.332(3) . ?
N2 C9 1.347(3) . ?
O1 C21 1.201(3) . ?
O2 C21 1.342(3) . ?
O2 C22 1.455(4) . ?
C1 C6 1.356(5) . ?
C1 C2 1.357(5) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(4) . ?
C4 C7 1.502(4) . ?
C5 C6 1.385(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.519(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.404(4) . ?
C10 C11 1.375(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.420(3) . ?
C11 C15 1.491(3) . ?
C12 C13 1.388(3) . ?
C12 C21 1.491(4) . ?
C13 C14 1.513(4) . ?
C15 C20 1.387(4) . ?
C15 C16 1.387(4) . ?
C16 C17 1.383(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.361(4) . ?
C19 C20 1.382(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C22 C23 1.430(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C9 N1 C8 123.0(2) . . ?
C9 N1 H1 118.5 . . ?
C8 N1 H1 118.5 . . ?
C13 N2 C9 117.6(2) . . ?
C21 O2 C22 118.9(2) . . ?
C6 C1 C2 122.4(3) . . ?
C6 C1 F1 118.4(4) . . ?
C2 C1 F1 119.1(4) . . ?
C1 C2 C3 118.4(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C7 121.1(3) . . ?
C5 C4 C7 121.1(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C4 C7 C8 111.1(2) . . ?
C4 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C4 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 C7 114.0(2) . . ?
N1 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
N1 C9 N2 116.5(2) . . ?
N1 C9 C10 122.1(2) . . ?
N2 C9 C10 121.4(2) . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 118.7(2) . . ?
C10 C11 C15 118.9(2) . . ?
C12 C11 C15 122.3(2) . . ?
C13 C12 C11 116.4(2) . . ?
C13 C12 C21 121.9(2) . . ?
C11 C12 C21 121.7(2) . . ?
N2 C13 C12 125.5(2) . . ?
N2 C13 C14 111.7(2) . . ?
C12 C13 C14 122.8(2) . . ?
F2 C14 F3 107.3(2) . . ?
F2 C14 F4 105.9(2) . . ?
F3 C14 F4 105.8(2) . . ?
F2 C14 C13 112.7(2) . . ?
F3 C14 C13 111.8(2) . . ?
F4 C14 C13 112.9(2) . . ?
C20 C15 C16 118.1(3) . . ?
C20 C15 C11 122.0(2) . . ?
C16 C15 C11 119.8(2) . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 118.5(3) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
C17 C18 F5 118.9(3) . . ?
C17 C18 C19 122.8(3) . . ?
F5 C18 C19 118.4(3) . . ?
C18 C19 C20 118.3(3) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 H19 120.9 . . ?
C19 C20 C15 121.3(3) . . ?
C19 C20 H20 119.3 . . ?
C15 C20 H20 119.3 . . ?
O1 C21 O2 124.1(3) . . ?
O1 C21 C12 125.6(3) . . ?
O2 C21 C12 110.3(2) . . ?
C23 C22 O2 112.6(3) . . ?
C23 C22 H22A 109.1 . . ?
O2 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
O2 C22 H22B 109.1 . . ?
H22A C22 H22B 107.8 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C6 C1 C2 C3 -0.2(5) . . . . ?
F1 C1 C2 C3 178.9(3) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C2 C3 C4 C7 176.4(3) . . . . ?
C3 C4 C5 C6 -1.9(4) . . . . ?
C7 C4 C5 C6 -177.3(3) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
F1 C1 C6 C5 -179.8(3) . . . . ?
C4 C5 C6 C1 1.8(5) . . . . ?
C3 C4 C7 C8 -97.4(3) . . . . ?
C5 C4 C7 C8 77.9(3) . . . . ?
C9 N1 C8 C7 77.5(3) . . . . ?
C4 C7 C8 N1 179.0(2) . . . . ?
C8 N1 C9 N2 -1.2(4) . . . . ?
C8 N1 C9 C10 177.5(3) . . . . ?
C13 N2 C9 N1 179.3(2) . . . . ?
C13 N2 C9 C10 0.6(4) . . . . ?
N1 C9 C10 C11 -178.7(3) . . . . ?
N2 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 -0.1(4) . . . . ?
C9 C10 C11 C15 177.7(2) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C15 C11 C12 C13 -178.1(2) . . . . ?
C10 C11 C12 C21 -177.4(2) . . . . ?
C15 C11 C12 C21 4.9(4) . . . . ?
C9 N2 C13 C12 -1.1(4) . . . . ?
C9 N2 C13 C14 179.1(2) . . . . ?
C11 C12 C13 N2 1.0(4) . . . . ?
C21 C12 C13 N2 178.0(2) . . . . ?
C11 C12 C13 C14 -179.2(2) . . . . ?
C21 C12 C13 C14 -2.2(4) . . . . ?
N2 C13 C14 F2 -25.8(3) . . . . ?
C12 C13 C14 F2 154.4(3) . . . . ?
N2 C13 C14 F3 95.1(3) . . . . ?
C12 C13 C14 F3 -84.7(3) . . . . ?
N2 C13 C14 F4 -145.7(2) . . . . ?
C12 C13 C14 F4 34.5(4) . . . . ?
C10 C11 C15 C20 -128.3(3) . . . . ?
C12 C11 C15 C20 49.3(4) . . . . ?
C10 C11 C15 C16 50.5(4) . . . . ?
C12 C11 C15 C16 -131.8(3) . . . . ?
C20 C15 C16 C17 -0.6(4) . . . . ?
C11 C15 C16 C17 -179.5(3) . . . . ?
C15 C16 C17 C18 -0.2(5) . . . . ?
C16 C17 C18 F5 180.0(3) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C17 C18 C19 C20 -0.3(5) . . . . ?
F5 C18 C19 C20 -179.6(3) . . . . ?
C18 C19 C20 C15 -0.5(4) . . . . ?
C16 C15 C20 C19 1.0(4) . . . . ?
C11 C15 C20 C19 179.8(3) . . . . ?
C22 O2 C21 O1 -1.4(4) . . . . ?
C22 O2 C21 C12 177.4(3) . . . . ?
C13 C12 C21 O1 61.8(4) . . . . ?
C11 C12 C21 O1 -121.3(3) . . . . ?
C13 C12 C21 O2 -116.9(3) . . . . ?
C11 C12 C21 O2 59.9(3) . . . . ?
C21 O2 C22 C23 97.1(4) . . . . ?

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 2.35 3.206(3) 172.6 1_455
C7 H7A N2 0.97 2.70 3.201(4) 113.0 .
C8 H8B F3 0.97 2.52 3.361(3) 145.6 1_455
C19 H19 O1 0.93 2.63 3.521(4) 160.3 2_766

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.046

_shelxl_version_number           2014-3



