# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_d8v21803_0m
_database_code_depnum_ccdc_archive 'CCDC 2116700'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-10-20 deposited with the CCDC.	2022-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 F2 N O'
_chemical_formula_weight         311.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           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                   5.5106(2)
_cell_length_b                   7.7117(3)
_cell_length_c                   9.6692(3)
_cell_angle_alpha                70.0900(10)
_cell_angle_beta                 86.9720(10)
_cell_angle_gamma                85.4380(10)
_cell_volume                     384.97(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5270
_cell_measurement_theta_min      4.482
_cell_measurement_theta_max      54.200

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             162
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_T_max  0.7456
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7760
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.389
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2960
_reflns_number_gt                2800
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.988
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.981

_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-2013 (Sheldrick, 2013)'
_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)+(0.0453P)²+0.0240P] 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       0.17(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1299 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.2(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2960
_refine_ls_number_parameters     210
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0809
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.007
_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 0.2518(3) 0.8391(2) 0.35258(16) 0.0640(4) Uani 1 1 d . . . . .
F2 F 0.3483(3) 1.01369(19) 0.4747(2) 0.0728(5) Uani 1 1 d . . . . .
O1 O 0.1061(3) 0.7444(3) 0.6698(2) 0.0634(5) Uani 1 1 d . . . . .
N1 N 0.6864(3) 0.2985(2) 0.6301(2) 0.0433(5) Uani 1 1 d . . . . .
C1 C 0.5268(4) 0.2163(3) 0.7462(2) 0.0463(5) Uani 1 1 d . . . . .
C2 C 0.5302(6) 0.0325(4) 0.8391(3) 0.0637(7) Uani 1 1 d . . . . .
H2 H 0.6494 -0.0552 0.8292 0.076 Uiso 1 1 calc R U . . .
C3 C 0.3483(7) -0.0126(4) 0.9462(4) 0.0773(9) Uani 1 1 d . . . . .
H3 H 0.3450 -0.1338 1.0104 0.093 Uiso 1 1 calc R U . . .
C4 C 0.1693(6) 0.1186(5) 0.9607(3) 0.0732(8) Uani 1 1 d . . . . .
H4 H 0.0481 0.0831 1.0336 0.088 Uiso 1 1 calc R U . . .
C5 C 0.1684(5) 0.3002(4) 0.8692(3) 0.0580(7) Uani 1 1 d . . . . .
H5 H 0.0492 0.3874 0.8801 0.070 Uiso 1 1 calc R U . . .
C6 C 0.3508(4) 0.3501(3) 0.7599(2) 0.0443(5) Uani 1 1 d . . . . .
C7 C 0.4078(4) 0.5196(3) 0.6459(2) 0.0403(5) Uani 1 1 d . . . . .
C8 C 0.2855(4) 0.6989(3) 0.6066(2) 0.0445(5) Uani 1 1 d . . . . .
C9 C 0.3896(4) 0.8406(3) 0.4668(3) 0.0469(5) Uani 1 1 d . . . . .
C10 C 0.6562(4) 0.8105(3) 0.4321(3) 0.0471(5) Uani 1 1 d . . . . .
H10A H 0.7511 0.8412 0.5012 0.056 Uiso 1 1 calc R U . . .
H10B H 0.6943 0.8944 0.3344 0.056 Uiso 1 1 calc R U . . .
C11 C 0.7342(4) 0.6108(3) 0.4388(2) 0.0397(5) Uani 1 1 d . . . . .
H11 H 0.9098 0.5926 0.4552 0.048 Uiso 1 1 calc R U . . .
C12 C 0.6138(4) 0.4795(3) 0.5703(2) 0.0382(5) Uani 1 1 d . . . . .
C13 C 0.6934(4) 0.5723(3) 0.2971(2) 0.0411(5) Uani 1 1 d . . . . .
C14 C 0.5078(4) 0.4691(4) 0.2835(3) 0.0539(6) Uani 1 1 d . . . . .
H14 H 0.3997 0.4218 0.3622 0.065 Uiso 1 1 calc R U . . .
C15 C 0.4821(5) 0.4357(5) 0.1536(3) 0.0677(8) Uani 1 1 d . . . . .
H15 H 0.3568 0.3660 0.1456 0.081 Uiso 1 1 calc R U . . .
C16 C 0.6394(6) 0.5044(5) 0.0365(3) 0.0689(8) Uani 1 1 d . . . . .
H16 H 0.6204 0.4823 -0.0509 0.083 Uiso 1 1 calc R U . . .
C17 C 0.8258(5) 0.6062(4) 0.0490(3) 0.0623(7) Uani 1 1 d . . . . .
H17 H 0.9338 0.6525 -0.0300 0.075 Uiso 1 1 calc R U . . .
C18 C 0.8528(4) 0.6398(3) 0.1785(3) 0.0505(6) Uani 1 1 d . . . . .
H18 H 0.9794 0.7085 0.1863 0.061 Uiso 1 1 calc R U . . .
C19 C 0.8909(5) 0.2018(3) 0.5796(3) 0.0536(6) Uani 1 1 d . . . . .
H19A H 0.8396 0.1625 0.5022 0.080 Uiso 1 1 calc R U . . .
H19B H 0.9474 0.0958 0.6600 0.080 Uiso 1 1 calc R U . . .
H19C H 1.0204 0.2832 0.5433 0.080 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 C9 1.377(3) . ?
F2 C9 1.363(3) . ?
O1 C8 1.225(3) . ?
N1 C12 1.352(3) . ?
N1 C1 1.391(3) . ?
N1 C19 1.456(3) . ?
C1 C6 1.394(3) . ?
C1 C2 1.395(4) . ?
C2 C3 1.378(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(3) . ?
C7 C12 1.388(3) . ?
C7 C8 1.425(3) . ?
C8 C9 1.537(3) . ?
C9 C10 1.507(3) . ?
C10 C11 1.546(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.491(3) . ?
C11 C13 1.529(3) . ?
C11 H11 0.9800 . ?
C13 C14 1.383(3) . ?
C13 C18 1.384(3) . ?
C14 C15 1.381(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.380(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C12 N1 C1 108.54(17) . . ?
C12 N1 C19 126.46(19) . . ?
C1 N1 C19 124.96(19) . . ?
N1 C1 C6 108.85(19) . . ?
N1 C1 C2 128.7(2) . . ?
C6 C1 C2 122.5(2) . . ?
C3 C2 C1 116.8(3) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.4(3) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C5 119.5(2) . . ?
C1 C6 C7 106.00(19) . . ?
C5 C6 C7 134.5(2) . . ?
C12 C7 C8 122.9(2) . . ?
C12 C7 C6 106.9(2) . . ?
C8 C7 C6 130.2(2) . . ?
O1 C8 C7 126.3(2) . . ?
O1 C8 C9 119.4(2) . . ?
C7 C8 C9 114.28(18) . . ?
F2 C9 F1 105.45(18) . . ?
F2 C9 C10 108.71(19) . . ?
F1 C9 C10 110.1(2) . . ?
F2 C9 C8 109.47(19) . . ?
F1 C9 C8 106.27(18) . . ?
C10 C9 C8 116.28(19) . . ?
C9 C10 C11 114.02(18) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C13 112.78(17) . . ?
C12 C11 C10 108.72(17) . . ?
C13 C11 C10 114.23(19) . . ?
C12 C11 H11 106.9 . . ?
C13 C11 H11 106.9 . . ?
C10 C11 H11 106.9 . . ?
N1 C12 C7 109.70(19) . . ?
N1 C12 C11 123.99(18) . . ?
C7 C12 C11 126.3(2) . . ?
C14 C13 C18 118.6(2) . . ?
C14 C13 C11 122.8(2) . . ?
C18 C13 C11 118.6(2) . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.6(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 119.6(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 120.7(2) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C12 N1 C1 C6 -0.5(2) . . . . ?
C19 N1 C1 C6 -178.3(2) . . . . ?
C12 N1 C1 C2 179.9(2) . . . . ?
C19 N1 C1 C2 2.1(4) . . . . ?
N1 C1 C2 C3 -180.0(3) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
C1 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 -0.7(6) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
N1 C1 C6 C5 179.7(2) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
N1 C1 C6 C7 0.4(2) . . . . ?
C2 C1 C6 C7 -180.0(2) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 C7 179.2(3) . . . . ?
C1 C6 C7 C12 -0.2(2) . . . . ?
C5 C6 C7 C12 -179.3(3) . . . . ?
C1 C6 C7 C8 178.3(2) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C12 C7 C8 O1 -178.6(2) . . . . ?
C6 C7 C8 O1 3.1(4) . . . . ?
C12 C7 C8 C9 4.2(3) . . . . ?
C6 C7 C8 C9 -174.0(2) . . . . ?
O1 C8 C9 F2 30.8(3) . . . . ?
C7 C8 C9 F2 -151.84(19) . . . . ?
O1 C8 C9 F1 -82.6(3) . . . . ?
C7 C8 C9 F1 94.7(2) . . . . ?
O1 C8 C9 C10 154.5(2) . . . . ?
C7 C8 C9 C10 -28.2(3) . . . . ?
F2 C9 C10 C11 172.90(18) . . . . ?
F1 C9 C10 C11 -72.0(3) . . . . ?
C8 C9 C10 C11 48.9(3) . . . . ?
C9 C10 C11 C12 -42.2(3) . . . . ?
C9 C10 C11 C13 84.7(2) . . . . ?
C1 N1 C12 C7 0.4(2) . . . . ?
C19 N1 C12 C7 178.2(2) . . . . ?
C1 N1 C12 C11 -177.12(18) . . . . ?
C19 N1 C12 C11 0.6(3) . . . . ?
C8 C7 C12 N1 -178.7(2) . . . . ?
C6 C7 C12 N1 -0.2(2) . . . . ?
C8 C7 C12 C11 -1.3(3) . . . . ?
C6 C7 C12 C11 177.30(19) . . . . ?
C13 C11 C12 N1 69.6(3) . . . . ?
C10 C11 C12 N1 -162.66(19) . . . . ?
C13 C11 C12 C7 -107.5(2) . . . . ?
C10 C11 C12 C7 20.2(3) . . . . ?
C12 C11 C13 C14 19.0(3) . . . . ?
C10 C11 C13 C14 -105.8(2) . . . . ?
C12 C11 C13 C18 -159.32(19) . . . . ?
C10 C11 C13 C18 75.9(2) . . . . ?
C18 C13 C14 C15 -0.5(4) . . . . ?
C11 C13 C14 C15 -178.8(2) . . . . ?
C13 C14 C15 C16 -0.1(5) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C16 C17 C18 C13 -0.2(4) . . . . ?
C14 C13 C18 C17 0.6(4) . . . . ?
C11 C13 C18 C17 179.0(2) . . . . ?

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
C10 H10A O1 0.97 2.51 3.360(3) 145.8 1_655

_refine_diff_density_max         0.121
_refine_diff_density_min         -0.094
_refine_diff_density_rms         0.021

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_d8v21903_0m
_database_code_depnum_ccdc_archive 'CCDC 2123014'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-11-19 deposited with the CCDC.	2022-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 F2 N O'
_chemical_formula_weight         289.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.9237(4)
_cell_length_b                   10.5309(4)
_cell_length_c                   12.4165(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.4820(10)
_cell_angle_gamma                90
_cell_volume                     1418.93(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5040
_cell_measurement_theta_min      5.288
_cell_measurement_theta_max      53.529

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6680
_exptl_absorpt_correction_T_max  0.7456
_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                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12351
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.606
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2761
_reflns_number_gt                2125
_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-2013 (Sheldrick, 2013)'
_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)+(0.0495P)²+0.2509P] 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       0.043(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2761
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1043
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.001

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 0.78908(9) 0.84208(13) 0.39143(10) 0.0957(4) Uani 1 1 d . . . . .
F2 F 0.68096(14) 0.94797(13) 0.46413(12) 0.1191(5) Uani 1 1 d . . . . .
O1 O 0.75524(13) 0.74325(17) 0.59955(11) 0.0963(5) Uani 1 1 d . . . . .
N1 N 0.53343(11) 0.47932(13) 0.29045(11) 0.0566(4) Uani 1 1 d . . . . .
C1 C 0.57576(14) 0.40724(17) 0.39422(14) 0.0608(4) Uani 1 1 d . . . . .
C2 C 0.55768(19) 0.27915(19) 0.40880(19) 0.0775(6) Uani 1 1 d . . . . .
H2 H 0.5111 0.2277 0.3450 0.093 Uiso 1 1 calc R U . . .
C3 C 0.6122(2) 0.2322(2) 0.5225(2) 0.0919(7) Uani 1 1 d . . . . .
H3 H 0.6033 0.1466 0.5355 0.110 Uiso 1 1 calc R U . . .
C4 C 0.6796(2) 0.3089(3) 0.6175(2) 0.0927(8) Uani 1 1 d . . . . .
H4 H 0.7142 0.2739 0.6930 0.111 Uiso 1 1 calc R U . . .
C5 C 0.69696(17) 0.4363(2) 0.60299(16) 0.0810(6) Uani 1 1 d . . . . .
H5 H 0.7423 0.4873 0.6676 0.097 Uiso 1 1 calc R U . . .
C6 C 0.64441(14) 0.48656(18) 0.48829(13) 0.0626(5) Uani 1 1 d . . . . .
C7 C 0.64343(13) 0.60974(17) 0.43858(13) 0.0573(4) Uani 1 1 d . . . . .
C8 C 0.69716(14) 0.7265(2) 0.49292(14) 0.0678(5) Uani 1 1 d . . . . .
C9 C 0.68134(16) 0.83717(18) 0.40763(16) 0.0708(5) Uani 1 1 d . . . . .
C10 C 0.56870(14) 0.83317(15) 0.29119(14) 0.0593(4) Uani 1 1 d . . . . .
H10 H 0.4979 0.8420 0.3114 0.071 Uiso 1 1 calc R U . . .
C11 C 0.55877(17) 0.94332(18) 0.20745(17) 0.0726(5) Uani 1 1 d . . . . .
H11A H 0.4731 0.9536 0.1529 0.087 Uiso 1 1 calc R U . . .
H11B H 0.5846 1.0208 0.2535 0.087 Uiso 1 1 calc R U . . .
C12 C 0.63533(17) 0.92618(19) 0.13647(17) 0.0734(5) Uani 1 1 d . . . . .
H12A H 0.6169 0.9943 0.0791 0.088 Uiso 1 1 calc R U . . .
H12B H 0.7221 0.9313 0.1892 0.088 Uiso 1 1 calc R U . . .
C13 C 0.60951(18) 0.80035(18) 0.07304(16) 0.0718(5) Uani 1 1 d . . . . .
H13A H 0.6619 0.7910 0.0310 0.086 Uiso 1 1 calc R U . . .
H13B H 0.5244 0.7981 0.0153 0.086 Uiso 1 1 calc R U . . .
C14 C 0.63287(16) 0.69087(17) 0.15949(15) 0.0647(5) Uani 1 1 d . . . . .
H14A H 0.7192 0.6898 0.2142 0.078 Uiso 1 1 calc R U . . .
H14B H 0.6143 0.6112 0.1164 0.078 Uiso 1 1 calc R U . . .
C15 C 0.55267(13) 0.70386(15) 0.22924(13) 0.0529(4) Uani 1 1 d . . . . .
H15 H 0.4664 0.6976 0.1721 0.064 Uiso 1 1 calc R U . . .
C16 C 0.57501(12) 0.60012(15) 0.31720(12) 0.0513(4) Uani 1 1 d . . . . .
C17 C 0.45306(19) 0.43080(19) 0.17403(16) 0.0804(6) Uani 1 1 d . . . . .
H17A H 0.4183 0.5006 0.1208 0.121 Uiso 1 1 calc R U . . .
H17B H 0.3881 0.3816 0.1799 0.121 Uiso 1 1 calc R U . . .
H17C H 0.4999 0.3782 0.1446 0.121 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 C9 1.381(2) . ?
F2 C9 1.362(2) . ?
O1 C8 1.2263(19) . ?
N1 C16 1.356(2) . ?
N1 C1 1.397(2) . ?
N1 C17 1.456(2) . ?
C1 C2 1.390(3) . ?
C1 C6 1.393(2) . ?
C2 C3 1.378(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.434(2) . ?
C7 C16 1.389(2) . ?
C7 C8 1.421(2) . ?
C8 C9 1.533(3) . ?
C9 C10 1.512(2) . ?
C10 C11 1.529(2) . ?
C10 C15 1.537(2) . ?
C10 H10 0.9800 . ?
C11 C12 1.520(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.507(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.520(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.539(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.489(2) . ?
C15 H15 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C16 N1 C1 109.16(13) . . ?
C16 N1 C17 126.57(14) . . ?
C1 N1 C17 124.22(15) . . ?
C2 C1 C6 122.82(17) . . ?
C2 C1 N1 129.14(17) . . ?
C6 C1 N1 108.04(15) . . ?
C3 C2 C1 116.7(2) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 121.53(19) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C6 118.1(2) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 119.08(19) . . ?
C1 C6 C7 106.52(14) . . ?
C5 C6 C7 134.40(19) . . ?
C16 C7 C8 121.67(16) . . ?
C16 C7 C6 107.30(15) . . ?
C8 C7 C6 131.03(15) . . ?
O1 C8 C7 125.39(19) . . ?
O1 C8 C9 119.27(17) . . ?
C7 C8 C9 115.33(14) . . ?
F2 C9 F1 104.17(14) . . ?
F2 C9 C10 108.96(15) . . ?
F1 C9 C10 111.90(14) . . ?
F2 C9 C8 108.74(15) . . ?
F1 C9 C8 105.87(15) . . ?
C10 C9 C8 116.45(14) . . ?
C9 C10 C11 114.63(14) . . ?
C9 C10 C15 112.35(14) . . ?
C11 C10 C15 111.92(13) . . ?
C9 C10 H10 105.7 . . ?
C11 C10 H10 105.7 . . ?
C15 C10 H10 105.7 . . ?
C12 C11 C10 114.10(15) . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 111.47(15) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 C14 111.09(15) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 110.80(14) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C10 109.62(12) . . ?
C16 C15 C14 112.55(13) . . ?
C10 C15 C14 112.52(13) . . ?
C16 C15 H15 107.3 . . ?
C10 C15 H15 107.3 . . ?
C14 C15 H15 107.3 . . ?
N1 C16 C7 108.97(14) . . ?
N1 C16 C15 124.95(13) . . ?
C7 C16 C15 126.07(14) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C16 N1 C1 C2 -178.83(16) . . . . ?
C17 N1 C1 C2 3.6(3) . . . . ?
C16 N1 C1 C6 0.77(16) . . . . ?
C17 N1 C1 C6 -176.83(15) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
N1 C1 C2 C3 179.13(16) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?
N1 C1 C6 C5 179.79(13) . . . . ?
C2 C1 C6 C7 179.28(15) . . . . ?
N1 C1 C6 C7 -0.36(16) . . . . ?
C4 C5 C6 C1 0.9(2) . . . . ?
C4 C5 C6 C7 -178.88(17) . . . . ?
C1 C6 C7 C16 -0.17(16) . . . . ?
C5 C6 C7 C16 179.66(16) . . . . ?
C1 C6 C7 C8 179.34(15) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C16 C7 C8 O1 177.53(16) . . . . ?
C6 C7 C8 O1 -1.9(3) . . . . ?
C16 C7 C8 C9 -3.9(2) . . . . ?
C6 C7 C8 C9 176.68(15) . . . . ?
O1 C8 C9 F2 -30.0(2) . . . . ?
C7 C8 C9 F2 151.32(14) . . . . ?
O1 C8 C9 F1 81.43(18) . . . . ?
C7 C8 C9 F1 -97.26(15) . . . . ?
O1 C8 C9 C10 -153.49(16) . . . . ?
C7 C8 C9 C10 27.8(2) . . . . ?
F2 C9 C10 C11 58.38(19) . . . . ?
F1 C9 C10 C11 -56.3(2) . . . . ?
C8 C9 C10 C11 -178.23(14) . . . . ?
F2 C9 C10 C15 -172.38(14) . . . . ?
F1 C9 C10 C15 72.97(18) . . . . ?
C8 C9 C10 C15 -48.99(19) . . . . ?
C9 C10 C11 C12 81.59(19) . . . . ?
C15 C10 C11 C12 -47.86(19) . . . . ?
C10 C11 C12 C13 52.3(2) . . . . ?
C11 C12 C13 C14 -57.0(2) . . . . ?
C12 C13 C14 C15 58.16(19) . . . . ?
C9 C10 C15 C16 44.00(17) . . . . ?
C11 C10 C15 C16 174.63(12) . . . . ?
C9 C10 C15 C14 -82.06(17) . . . . ?
C11 C10 C15 C14 48.57(17) . . . . ?
C13 C14 C15 C16 -178.57(13) . . . . ?
C13 C14 C15 C10 -54.11(17) . . . . ?
C1 N1 C16 C7 -0.89(16) . . . . ?
C17 N1 C16 C7 176.64(15) . . . . ?
C1 N1 C16 C15 177.76(13) . . . . ?
C17 N1 C16 C15 -4.7(2) . . . . ?
C8 C7 C16 N1 -178.91(13) . . . . ?
C6 C7 C16 N1 0.65(16) . . . . ?
C8 C7 C16 C15 2.5(2) . . . . ?
C6 C7 C16 C15 -177.98(13) . . . . ?
C10 C15 C16 N1 158.61(13) . . . . ?
C14 C15 C16 N1 -75.35(18) . . . . ?
C10 C15 C16 C7 -22.97(19) . . . . ?
C14 C15 C16 C7 103.07(17) . . . . ?

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
C15 H15 O1 0.98 2.38 3.2783(19) 152.3 4_575

_refine_diff_density_max         0.127
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.024

_shelxl_version_number           2013-4

