# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_cd16720
_database_code_depnum_ccdc_archive 'CCDC 1521105'
_audit_update_record             
;
2016-12-07 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 Cl F3 N O5'
_chemical_formula_weight         481.84

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'
Cl Cl 0.1484 0.1585 '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                   7.3052(11)
_cell_length_b                   10.5757(16)
_cell_length_c                   14.449(2)
_cell_angle_alpha                88.853(3)
_cell_angle_beta                 83.694(3)
_cell_angle_gamma                77.708(3)
_cell_volume                     1084.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1798
_cell_measurement_theta_min      4.848
_cell_measurement_theta_max      46.217

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.238
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6761
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6268
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.971
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4012
_reflns_number_gt                3024
_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 SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0595P)²+0.1782P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4012
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.022
_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
Cl1 Cl 0.27266(10) 0.24334(7) -0.27216(4) 0.0716(2) Uani 1 1 d . . . . .
F1 F -0.03170(18) 0.24923(12) 0.15572(10) 0.0636(4) Uani 1 1 d . . . . .
F2 F -0.02968(19) 0.39836(13) 0.05324(10) 0.0696(4) Uani 1 1 d . . . . .
F3 F 0.0588(2) 0.42189(13) 0.18727(10) 0.0726(4) Uani 1 1 d . . . . .
N1 N 0.2417(2) -0.00682(16) 0.09785(12) 0.0407(4) Uani 1 1 d . . . . .
O1 O 0.3427(2) 0.20205(12) 0.16359(9) 0.0455(4) Uani 1 1 d . . . . .
O2 O 0.5774(2) 0.45673(15) 0.16407(13) 0.0656(5) Uani 1 1 d . . . . .
O3 O 0.2345(2) -0.21402(14) 0.05994(10) 0.0574(4) Uani 1 1 d . . . . .
O4 O 0.1078(3) -0.2082(2) 0.56776(13) 0.0872(6) Uani 1 1 d . . . . .
O5 O 0.1827(4) -0.40891(18) 0.51315(12) 0.0922(7) Uani 1 1 d . . . . .
C1 C 0.2512(3) 0.05323(18) 0.01027(13) 0.0379(4) Uani 1 1 d . . . . .
C2 C 0.2417(3) -0.0142(2) -0.07039(14) 0.0447(5) Uani 1 1 d . . . . .
H2 H 0.2304 -0.1001 -0.0660 0.054 Uiso 1 1 calc R U . . .
C3 C 0.2487(3) 0.0437(2) -0.15627(14) 0.0474(5) Uani 1 1 d . . . . .
H3 H 0.2429 -0.0029 -0.2094 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2644(3) 0.1706(2) -0.16345(14) 0.0468(5) Uani 1 1 d . . . . .
C5 C 0.2735(3) 0.2396(2) -0.08555(14) 0.0457(5) Uani 1 1 d . . . . .
H5 H 0.2835 0.3257 -0.0915 0.055 Uiso 1 1 calc R U . . .
C6 C 0.2682(3) 0.18346(18) 0.00239(13) 0.0378(4) Uani 1 1 d . . . . .
C7 C 0.2667(3) 0.27284(18) 0.08428(13) 0.0407(5) Uani 1 1 d . . . . .
C8 C 0.3854(3) 0.37665(19) 0.06311(15) 0.0477(5) Uani 1 1 d . . . . .
H8A H 0.4752 0.3532 0.0084 0.057 Uiso 1 1 calc R U . . .
H8B H 0.3053 0.4604 0.0529 0.057 Uiso 1 1 calc R U . . .
C9 C 0.4846(3) 0.37932(19) 0.14785(16) 0.0486(5) Uani 1 1 d . . . . .
C10 C 0.4484(3) 0.2718(2) 0.20774(16) 0.0483(5) Uani 1 1 d . . . . .
C11 C 0.5021(4) 0.2435(3) 0.29108(18) 0.0684(7) Uani 1 1 d . . . . .
H11 H 0.5795 0.2938 0.3118 0.082 Uiso 1 1 calc R U . . .
C12 C 0.4555(6) 0.1422(3) 0.3563(2) 0.1019(11) Uani 1 1 d . . . . .
H12A H 0.5681 0.0751 0.3598 0.122 Uiso 1 1 calc R U . . .
H12B H 0.3627 0.1031 0.3313 0.122 Uiso 1 1 calc R U . . .
C13 C 0.3812(6) 0.1899(5) 0.4521(2) 0.1282(15) Uani 1 1 d . . . . .
H13A H 0.4728 0.2275 0.4780 0.192 Uiso 1 1 calc R U . . .
H13B H 0.3557 0.1190 0.4902 0.192 Uiso 1 1 calc R U . . .
H13C H 0.2670 0.2541 0.4498 0.192 Uiso 1 1 calc R U . . .
C14 C 0.0641(3) 0.3359(2) 0.12006(15) 0.0494(5) Uani 1 1 d . . . . .
C15 C 0.2296(3) -0.13125(18) 0.11807(14) 0.0407(5) Uani 1 1 d . . . . .
C16 C 0.2110(3) -0.16325(18) 0.21983(13) 0.0395(5) Uani 1 1 d . . . . .
C17 C 0.2598(3) -0.2925(2) 0.24297(16) 0.0539(6) Uani 1 1 d . . . . .
H17 H 0.3048 -0.3538 0.1961 0.065 Uiso 1 1 calc R U . . .
C18 C 0.2430(3) -0.3318(2) 0.33402(16) 0.0579(6) Uani 1 1 d . . . . .
H18 H 0.2769 -0.4193 0.3483 0.069 Uiso 1 1 calc R U . . .
C19 C 0.1761(3) -0.2426(2) 0.40438(15) 0.0502(5) Uani 1 1 d . . . . .
C20 C 0.1259(3) -0.1128(2) 0.38184(15) 0.0555(6) Uani 1 1 d . . . . .
H20 H 0.0807 -0.0517 0.4288 0.067 Uiso 1 1 calc R U . . .
C21 C 0.1426(3) -0.07361(19) 0.29030(14) 0.0489(5) Uani 1 1 d . . . . .
H21 H 0.1076 0.0137 0.2759 0.059 Uiso 1 1 calc R U . . .
C22 C 0.1517(4) -0.2813(3) 0.50344(18) 0.0608(6) Uani 1 1 d . . . . .
C23 C 0.1554(7) -0.4586(3) 0.6062(2) 0.1199(15) Uani 1 1 d . . . . .
H23A H 0.0699 -0.3940 0.6446 0.180 Uiso 1 1 calc R U . . .
H23B H 0.2742 -0.4801 0.6315 0.180 Uiso 1 1 calc R U . . .
H23C H 0.1038 -0.5346 0.6043 0.180 Uiso 1 1 calc R U . . .
H1 H 0.246(3) 0.038(2) 0.1430(15) 0.046(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.736(2) . ?
F1 C14 1.330(2) . ?
F2 C14 1.329(3) . ?
F3 C14 1.336(2) . ?
N1 C15 1.361(2) . ?
N1 C1 1.406(2) . ?
N1 H1 0.82(2) . ?
O1 C10 1.384(2) . ?
O1 C7 1.453(2) . ?
O2 C9 1.210(2) . ?
O3 C15 1.218(2) . ?
O4 C22 1.192(3) . ?
O5 C22 1.328(3) . ?
O5 C23 1.442(3) . ?
C1 C2 1.394(3) . ?
C1 C6 1.410(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.527(3) . ?
C7 C14 1.526(3) . ?
C7 C8 1.545(3) . ?
C8 C9 1.493(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.466(3) . ?
C10 C11 1.316(3) . ?
C11 C12 1.482(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.487(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.500(3) . ?
C16 C17 1.381(3) . ?
C16 C21 1.382(3) . ?
C17 C18 1.372(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(3) . ?
C19 C22 1.483(3) . ?
C20 C21 1.378(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
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
C15 N1 C1 128.49(18) . . ?
C15 N1 H1 115.0(15) . . ?
C1 N1 H1 116.5(15) . . ?
C10 O1 C7 110.83(14) . . ?
C22 O5 C23 117.3(2) . . ?
C2 C1 N1 120.72(17) . . ?
C2 C1 C6 118.65(17) . . ?
N1 C1 C6 120.62(17) . . ?
C3 C2 C1 121.32(19) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C4 C3 C2 119.8(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.36(19) . . ?
C5 C4 Cl1 120.11(16) . . ?
C3 C4 Cl1 119.54(17) . . ?
C4 C5 C6 121.26(19) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.64(18) . . ?
C5 C6 C7 116.22(17) . . ?
C1 C6 C7 124.98(17) . . ?
O1 C7 C14 104.67(15) . . ?
O1 C7 C6 111.99(15) . . ?
C14 C7 C6 109.87(17) . . ?
O1 C7 C8 104.94(16) . . ?
C14 C7 C8 110.54(16) . . ?
C6 C7 C8 114.33(16) . . ?
C9 C8 C7 104.52(17) . . ?
C9 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
O2 C9 C10 126.3(2) . . ?
O2 C9 C8 126.0(2) . . ?
C10 C9 C8 107.68(17) . . ?
C11 C10 O1 123.5(2) . . ?
C11 C10 C9 127.3(2) . . ?
O1 C10 C9 109.16(19) . . ?
C10 C11 C12 128.7(3) . . ?
C10 C11 H11 115.7 . . ?
C12 C11 H11 115.7 . . ?
C11 C12 C13 114.3(3) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
F2 C14 F1 107.39(19) . . ?
F2 C14 F3 107.10(17) . . ?
F1 C14 F3 107.00(17) . . ?
F2 C14 C7 112.07(17) . . ?
F1 C14 C7 111.82(16) . . ?
F3 C14 C7 111.18(18) . . ?
O3 C15 N1 124.38(19) . . ?
O3 C15 C16 120.33(17) . . ?
N1 C15 C16 115.28(17) . . ?
C17 C16 C21 118.68(19) . . ?
C17 C16 C15 116.66(18) . . ?
C21 C16 C15 124.61(17) . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 120.4(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C18 C19 C20 119.0(2) . . ?
C18 C19 C22 122.1(2) . . ?
C20 C19 C22 118.9(2) . . ?
C21 C20 C19 120.5(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C16 120.41(19) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
O4 C22 O5 123.0(2) . . ?
O4 C22 C19 125.1(2) . . ?
O5 C22 C19 112.0(2) . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O5 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
C15 N1 C1 C2 2.4(3) . . . . ?
C15 N1 C1 C6 -178.35(19) . . . . ?
N1 C1 C2 C3 179.29(19) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C2 C3 C4 Cl1 -179.85(16) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
Cl1 C4 C5 C6 -179.66(16) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 -176.19(18) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
N1 C1 C6 C5 -178.82(17) . . . . ?
C2 C1 C6 C7 175.59(18) . . . . ?
N1 C1 C6 C7 -3.7(3) . . . . ?
C10 O1 C7 C14 -98.93(18) . . . . ?
C10 O1 C7 C6 142.08(16) . . . . ?
C10 O1 C7 C8 17.5(2) . . . . ?
C5 C6 C7 O1 -154.66(17) . . . . ?
C1 C6 C7 O1 30.1(3) . . . . ?
C5 C6 C7 C14 89.5(2) . . . . ?
C1 C6 C7 C14 -85.8(2) . . . . ?
C5 C6 C7 C8 -35.5(2) . . . . ?
C1 C6 C7 C8 149.27(19) . . . . ?
O1 C7 C8 C9 -14.9(2) . . . . ?
C14 C7 C8 C9 97.4(2) . . . . ?
C6 C7 C8 C9 -137.99(17) . . . . ?
C7 C8 C9 O2 -172.0(2) . . . . ?
C7 C8 C9 C10 7.8(2) . . . . ?
C7 O1 C10 C11 166.1(2) . . . . ?
C7 O1 C10 C9 -13.0(2) . . . . ?
O2 C9 C10 C11 3.4(4) . . . . ?
C8 C9 C10 C11 -176.4(2) . . . . ?
O2 C9 C10 O1 -177.6(2) . . . . ?
C8 C9 C10 O1 2.6(2) . . . . ?
O1 C10 C11 C12 -4.1(5) . . . . ?
C9 C10 C11 C12 174.8(3) . . . . ?
C10 C11 C12 C13 -128.5(3) . . . . ?
O1 C7 C14 F2 -175.99(15) . . . . ?
C6 C7 C14 F2 -55.6(2) . . . . ?
C8 C7 C14 F2 71.5(2) . . . . ?
O1 C7 C14 F1 -55.3(2) . . . . ?
C6 C7 C14 F1 65.1(2) . . . . ?
C8 C7 C14 F1 -167.84(18) . . . . ?
O1 C7 C14 F3 64.18(19) . . . . ?
C6 C7 C14 F3 -175.41(15) . . . . ?
C8 C7 C14 F3 -48.3(2) . . . . ?
C1 N1 C15 O3 3.8(3) . . . . ?
C1 N1 C15 C16 -176.74(17) . . . . ?
O3 C15 C16 C17 20.1(3) . . . . ?
N1 C15 C16 C17 -159.34(19) . . . . ?
O3 C15 C16 C21 -157.4(2) . . . . ?
N1 C15 C16 C21 23.2(3) . . . . ?
C21 C16 C17 C18 -0.6(3) . . . . ?
C15 C16 C17 C18 -178.3(2) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C20 0.1(4) . . . . ?
C17 C18 C19 C22 178.6(2) . . . . ?
C18 C19 C20 C21 0.0(4) . . . . ?
C22 C19 C20 C21 -178.5(2) . . . . ?
C19 C20 C21 C16 -0.5(4) . . . . ?
C17 C16 C21 C20 0.8(3) . . . . ?
C15 C16 C21 C20 178.2(2) . . . . ?
C23 O5 C22 O4 2.0(4) . . . . ?
C23 O5 C22 C19 -177.4(3) . . . . ?
C18 C19 C22 O4 174.2(3) . . . . ?
C20 C19 C22 O4 -7.3(4) . . . . ?
C18 C19 C22 O5 -6.5(3) . . . . ?
C20 C19 C22 O5 172.0(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
N1 H1 O1 0.82(2) 2.05(2) 2.694(2) 135.5(19) .
C23 H23A F3 0.96 2.54 3.204(4) 126.3 2_556
C8 H8A O3 0.97 2.43 3.291(3) 147.6 2_655
C2 H2 O3 0.93 2.16 2.807(2) 125.7 .

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.049

_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_cd16063
_database_code_depnum_ccdc_archive 'CCDC 1451585'
_audit_update_record             
;
2016-02-03 deposited with the CCDC.
2017-08-29 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 H23 Cl F3 N O4'
_chemical_formula_weight         421.83

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'
Cl Cl 0.1484 0.1585 '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                   11.287(2)
_cell_length_b                   12.727(2)
_cell_length_c                   14.808(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.680(4)
_cell_angle_gamma                90
_cell_volume                     2066.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2364
_cell_measurement_theta_min      4.903
_cell_measurement_theta_max      44.637

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.235
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6080
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11575
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.051
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3849
_reflns_number_gt                2750
_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 SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0657P)²+0.8169P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3849
_refine_ls_number_parameters     292
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0568
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1427
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 1.19837(9) 1.23121(8) 1.04471(7) 0.0997(4) Uani 1 1 d . . . . .
F1 F 1.0630(2) 1.05168(16) 0.59521(13) 0.0983(7) Uani 1 1 d . . . . .
F2 F 1.1065(2) 1.17220(15) 0.69852(14) 0.0924(6) Uani 1 1 d . . . . .
F3 F 0.9220(2) 1.12565(15) 0.64632(13) 0.0906(6) Uani 1 1 d . . . . .
N1 N 0.80209(19) 1.00185(18) 0.78839(17) 0.0521(6) Uani 1 1 d . . . . .
O1 O 0.97010(14) 0.92344(13) 0.70921(12) 0.0511(5) Uani 1 1 d . . . . .
O2 O 1.03281(19) 0.76218(15) 0.77312(12) 0.0635(5) Uani 1 1 d . . . . .
H2 H 0.9803 0.7171 0.7567 0.095 Uiso 1 1 calc R U . . .
O3 O 1.1034(2) 0.63816(18) 0.61807(17) 0.0843(7) Uani 1 1 d . . . . .
O4 O 0.65087(18) 1.11571(17) 0.78974(16) 0.0785(7) Uani 1 1 d . . . . .
C1 C 1.0496(2) 1.00674(19) 0.74852(17) 0.0439(6) Uani 1 1 d . . . . .
C2 C 1.1773(2) 0.9588(2) 0.7705(2) 0.0565(7) Uani 1 1 d . . . . .
H2A H 1.2018 0.9371 0.8350 0.068 Uiso 1 1 calc R U . . .
H2B H 1.2366 1.0084 0.7579 0.068 Uiso 1 1 calc R U . . .
C3 C 1.1646(2) 0.8637(2) 0.7052(2) 0.0585(7) Uani 1 1 d . . . . .
H3A H 1.1762 0.8839 0.6447 0.070 Uiso 1 1 calc R U . . .
H3B H 1.2229 0.8093 0.7311 0.070 Uiso 1 1 calc R U . . .
C4 C 1.0356(2) 0.82740(19) 0.69856(17) 0.0452(6) Uani 1 1 d . . . . .
C5 C 0.9671(2) 0.78325(19) 0.60623(17) 0.0469(6) Uani 1 1 d . . . . .
H5A H 0.8834 0.7712 0.6096 0.056 Uiso 1 1 calc R U . . .
H5B H 0.9657 0.8366 0.5592 0.056 Uiso 1 1 calc R U . . .
C6 C 1.0146(3) 0.6833(2) 0.5736(2) 0.0556(7) Uani 1 1 d . . . . .
C7 C 0.9428(4) 0.6417(3) 0.4827(2) 0.0883(11) Uani 1 1 d . . . . .
H7A H 0.9955 0.6330 0.4410 0.132 Uiso 1 1 calc R U . . .
H7B H 0.8789 0.6904 0.4564 0.132 Uiso 1 1 calc R U . . .
H7C H 0.9077 0.5752 0.4924 0.132 Uiso 1 1 calc R U . . .
C8 C 1.0349(3) 1.0895(2) 0.6719(2) 0.0652(8) Uani 1 1 d . . . . .
C9 C 1.0154(2) 1.05708(18) 0.83273(16) 0.0430(6) Uani 1 1 d . . . . .
C10 C 1.1064(3) 1.1115(2) 0.89480(18) 0.0534(7) Uani 1 1 d . . . . .
H10 H 1.1845 1.1146 0.8845 0.064 Uiso 1 1 calc R U . . .
C11 C 1.0828(3) 1.1607(2) 0.97093(19) 0.0590(7) Uani 1 1 d . . . . .
C12 C 0.9700(3) 1.1553(2) 0.99001(19) 0.0612(8) Uani 1 1 d . . . . .
H12 H 0.9553 1.1871 1.0428 0.073 Uiso 1 1 calc R U . . .
C13 C 0.8789(3) 1.1018(2) 0.92933(18) 0.0560(7) Uani 1 1 d . . . . .
H13 H 0.8022 1.0969 0.9420 0.067 Uiso 1 1 calc R U . . .
C14 C 0.8988(2) 1.05488(19) 0.84964(17) 0.0458(6) Uani 1 1 d . . . . .
C15 C 0.6856(2) 1.0337(2) 0.76137(18) 0.0503(6) Uani 1 1 d . . . . .
C16 C 0.6002(2) 0.9622(2) 0.6934(2) 0.0562(7) Uani 1 1 d . . . . .
C17 C 0.6465(5) 0.9501(6) 0.6030(4) 0.0991(18) Uani 0.7 1 d . U P A 1
H17A H 0.5935 0.9034 0.5611 0.149 Uiso 0.7 1 calc R U P A 1
H17B H 0.7277 0.9219 0.6181 0.149 Uiso 0.7 1 calc R U P A 1
H17C H 0.6469 1.0176 0.5741 0.149 Uiso 0.7 1 calc R U P A 1
C18 C 0.6104(8) 0.8478(5) 0.7291(5) 0.105(2) Uani 0.6 1 d . U P A 1
H18A H 0.6079 0.8470 0.7935 0.158 Uiso 0.6 1 calc R U P A 1
H18B H 0.6861 0.8181 0.7225 0.158 Uiso 0.6 1 calc R U P A 1
H18C H 0.5438 0.8073 0.6937 0.158 Uiso 0.6 1 calc R U P A 1
C19 C 0.4732(9) 0.9925(9) 0.6771(8) 0.104(3) Uani 0.5 1 d . U P A 1
H19A H 0.4484 0.9915 0.7348 0.156 Uiso 0.5 1 calc R U P A 1
H19B H 0.4241 0.9441 0.6344 0.156 Uiso 0.5 1 calc R U P A 1
H19C H 0.4630 1.0621 0.6514 0.156 Uiso 0.5 1 calc R U P A 1
C17' C 0.6559(13) 0.8817(12) 0.6531(11) 0.096(3) Uani 0.3 1 d . U P A 2
H17D H 0.7002 0.9119 0.6116 0.144 Uiso 0.3 1 calc R U P A 2
H17E H 0.5944 0.8350 0.6190 0.144 Uiso 0.3 1 calc R U P A 2
H17F H 0.7109 0.8432 0.7010 0.144 Uiso 0.3 1 calc R U P A 2
C18' C 0.5274(10) 0.9054(9) 0.7559(8) 0.102(3) Uani 0.4 1 d . U P A 2
H18D H 0.4717 0.8562 0.7191 0.152 Uiso 0.4 1 calc R U P A 2
H18E H 0.4827 0.9562 0.7825 0.152 Uiso 0.4 1 calc R U P A 2
H18F H 0.5830 0.8686 0.8048 0.152 Uiso 0.4 1 calc R U P A 2
C19' C 0.4931(10) 1.0319(7) 0.6338(6) 0.093(3) Uani 0.5 1 d . U P A 2
H19D H 0.5254 1.0788 0.5949 0.140 Uiso 0.5 1 calc R U P A 2
H19E H 0.4560 1.0719 0.6747 0.140 Uiso 0.5 1 calc R U P A 2
H19F H 0.4330 0.9870 0.5958 0.140 Uiso 0.5 1 calc R U P A 2
H1 H 0.823(3) 0.956(2) 0.757(2) 0.057(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C11 1.740(3) . ?
F1 C8 1.339(3) . ?
F2 C8 1.329(4) . ?
F3 C8 1.323(4) . ?
N1 C15 1.343(3) . ?
N1 C14 1.414(3) . ?
O1 C1 1.421(3) . ?
O1 C4 1.456(3) . ?
O2 C4 1.388(3) . ?
O3 C6 1.206(3) . ?
O4 C15 1.223(3) . ?
C1 C2 1.528(3) . ?
C1 C8 1.528(4) . ?
C1 C9 1.530(3) . ?
C2 C3 1.534(4) . ?
C3 C4 1.509(4) . ?
C4 C5 1.511(3) . ?
C5 C6 1.504(4) . ?
C6 C7 1.494(4) . ?
C9 C10 1.391(3) . ?
C9 C14 1.397(3) . ?
C10 C11 1.369(4) . ?
C11 C12 1.370(4) . ?
C12 C13 1.375(4) . ?
C13 C14 1.387(4) . ?
C15 C16 1.521(4) . ?
C16 C17' 1.407(15) . ?
C16 C19 1.448(11) . ?
C16 C18 1.544(7) . ?
C16 C18' 1.553(11) . ?
C16 C17 1.556(6) . ?
C16 C19' 1.588(9) . ?

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
C15 N1 C14 126.8(2) . . ?
C1 O1 C4 112.52(17) . . ?
O1 C1 C2 105.16(19) . . ?
O1 C1 C8 105.3(2) . . ?
C2 C1 C8 111.4(2) . . ?
O1 C1 C9 112.91(19) . . ?
C2 C1 C9 113.6(2) . . ?
C8 C1 C9 108.2(2) . . ?
C1 C2 C3 103.8(2) . . ?
C4 C3 C2 103.2(2) . . ?
O2 C4 O1 108.0(2) . . ?
O2 C4 C3 109.6(2) . . ?
O1 C4 C3 104.04(19) . . ?
O2 C4 C5 113.2(2) . . ?
O1 C4 C5 104.25(18) . . ?
C3 C4 C5 116.9(2) . . ?
C6 C5 C4 117.4(2) . . ?
O3 C6 C7 121.8(3) . . ?
O3 C6 C5 122.7(3) . . ?
C7 C6 C5 115.5(3) . . ?
F3 C8 F2 106.7(3) . . ?
F3 C8 F1 106.7(2) . . ?
F2 C8 F1 106.7(3) . . ?
F3 C8 C1 112.4(3) . . ?
F2 C8 C1 112.0(2) . . ?
F1 C8 C1 112.1(2) . . ?
C10 C9 C14 118.2(2) . . ?
C10 C9 C1 117.2(2) . . ?
C14 C9 C1 124.6(2) . . ?
C11 C10 C9 121.0(3) . . ?
C10 C11 C12 121.2(2) . . ?
C10 C11 Cl1 119.4(2) . . ?
C12 C11 Cl1 119.4(2) . . ?
C11 C12 C13 118.5(3) . . ?
C12 C13 C14 121.5(3) . . ?
C13 C14 C9 119.5(2) . . ?
C13 C14 N1 119.7(2) . . ?
C9 C14 N1 120.7(2) . . ?
O4 C15 N1 121.8(2) . . ?
O4 C15 C16 122.2(2) . . ?
N1 C15 C16 116.1(2) . . ?
C17' C16 C15 116.1(5) . . ?
C19 C16 C15 113.5(5) . . ?
C19 C16 C18 107.4(6) . . ?
C15 C16 C18 110.7(3) . . ?
C17' C16 C18' 105.4(8) . . ?
C15 C16 C18' 103.1(4) . . ?
C19 C16 C17 113.8(5) . . ?
C15 C16 C17 109.8(3) . . ?
C18 C16 C17 100.8(5) . . ?
C17' C16 C19' 121.9(8) . . ?
C15 C16 C19' 108.3(4) . . ?
C18' C16 C19' 98.7(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 C1 C2 -3.5(3) . . . . ?
C4 O1 C1 C8 114.3(2) . . . . ?
C4 O1 C1 C9 -127.9(2) . . . . ?
O1 C1 C2 C3 22.8(3) . . . . ?
C8 C1 C2 C3 -90.7(3) . . . . ?
C9 C1 C2 C3 146.8(2) . . . . ?
C1 C2 C3 C4 -33.0(3) . . . . ?
C1 O1 C4 O2 98.7(2) . . . . ?
C1 O1 C4 C3 -17.6(3) . . . . ?
C1 O1 C4 C5 -140.6(2) . . . . ?
C2 C3 C4 O2 -84.4(3) . . . . ?
C2 C3 C4 O1 30.8(3) . . . . ?
C2 C3 C4 C5 145.1(2) . . . . ?
O2 C4 C5 C6 -64.2(3) . . . . ?
O1 C4 C5 C6 178.8(2) . . . . ?
C3 C4 C5 C6 64.6(3) . . . . ?
C4 C5 C6 O3 0.3(4) . . . . ?
C4 C5 C6 C7 179.0(3) . . . . ?
O1 C1 C8 F3 61.2(3) . . . . ?
C2 C1 C8 F3 174.6(2) . . . . ?
C9 C1 C8 F3 -59.8(3) . . . . ?
O1 C1 C8 F2 -178.8(2) . . . . ?
C2 C1 C8 F2 -65.3(3) . . . . ?
C9 C1 C8 F2 60.3(3) . . . . ?
O1 C1 C8 F1 -58.9(3) . . . . ?
C2 C1 C8 F1 54.5(3) . . . . ?
C9 C1 C8 F1 -179.9(2) . . . . ?
O1 C1 C9 C10 158.1(2) . . . . ?
C2 C1 C9 C10 38.5(3) . . . . ?
C8 C1 C9 C10 -85.8(3) . . . . ?
O1 C1 C9 C14 -24.0(3) . . . . ?
C2 C1 C9 C14 -143.7(2) . . . . ?
C8 C1 C9 C14 92.1(3) . . . . ?
C14 C9 C10 C11 0.7(4) . . . . ?
C1 C9 C10 C11 178.7(2) . . . . ?
C9 C10 C11 C12 2.0(4) . . . . ?
C9 C10 C11 Cl1 -178.04(19) . . . . ?
C10 C11 C12 C13 -1.9(4) . . . . ?
Cl1 C11 C12 C13 178.1(2) . . . . ?
C11 C12 C13 C14 -0.8(4) . . . . ?
C12 C13 C14 C9 3.4(4) . . . . ?
C12 C13 C14 N1 -179.1(2) . . . . ?
C10 C9 C14 C13 -3.3(4) . . . . ?
C1 C9 C14 C13 178.9(2) . . . . ?
C10 C9 C14 N1 179.3(2) . . . . ?
C1 C9 C14 N1 1.4(4) . . . . ?
C15 N1 C14 C13 42.0(4) . . . . ?
C15 N1 C14 C9 -140.6(3) . . . . ?
C14 N1 C15 O4 -0.8(4) . . . . ?
C14 N1 C15 C16 179.1(2) . . . . ?
O4 C15 C16 C17' 168.3(9) . . . . ?
N1 C15 C16 C17' -11.5(9) . . . . ?
O4 C15 C16 C19 -8.5(6) . . . . ?
N1 C15 C16 C19 171.7(6) . . . . ?
O4 C15 C16 C18 -129.4(5) . . . . ?
N1 C15 C16 C18 50.8(5) . . . . ?
O4 C15 C16 C18' -77.0(6) . . . . ?
N1 C15 C16 C18' 103.2(6) . . . . ?
O4 C15 C16 C17 120.1(4) . . . . ?
N1 C15 C16 C17 -59.7(4) . . . . ?
O4 C15 C16 C19' 27.0(6) . . . . ?
N1 C15 C16 C19' -152.9(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
N1 H1 O1 0.82(3) 1.99(3) 2.649(3) 137(3) .
C10 H10 O3 0.93 2.42 3.343(4) 170.4 2_756
C5 H5A O4 0.97 2.56 3.109(3) 115.8 2_646
C3 H3B F2 0.97 2.62 3.593(3) 175.7 2_746
O2 H2 O4 0.82 1.96 2.780(3) 176.0 2_646
N1 H1 O1 0.82(3) 1.99(3) 2.649(3) 137(3) .
C10 H10 O3 0.93 2.42 3.343(4) 170.4 2_756
C5 H5A O4 0.97 2.56 3.109(3) 115.8 2_646
C3 H3B F2 0.97 2.62 3.593(3) 175.7 2_746
O2 H2 O4 0.82 1.96 2.780(3) 176.0 2_646
N1 H1 O1 0.82(3) 1.99(3) 2.649(3) 137(3) .
N1 H1 O1 0.82(3) 1.99(3) 2.649(3) 137(3) .
N1 H1 O1 0.82(3) 1.99(3) 2.649(3) 137(3) .
O2 H2 O4 0.82 1.96 2.780(3) 176.0 2_646
C3 H3B F2 0.97 2.62 3.593(3) 175.7 2_746
C5 H5A O4 0.97 2.56 3.109(3) 115.8 2_646
C10 H10 O3 0.93 2.42 3.343(4) 170.4 2_756
N1 H1 O1 0.82(3) 1.99(3) 2.649(3) 137(3) .

_refine_diff_density_max         0.339
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.043

_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_cd16477
_database_code_depnum_ccdc_archive 'CCDC 1500323'
_audit_update_record             
;
2016-08-22 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 Cl F3 N O3'
_chemical_formula_weight         423.81

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   21.872(3)
_cell_length_b                   7.6040(10)
_cell_length_c                   24.313(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.597(3)
_cell_angle_gamma                90
_cell_volume                     3785.2(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2023
_cell_measurement_theta_min      5.715
_cell_measurement_theta_max      45.387

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.254
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6195
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10493
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.790
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3513
_reflns_number_gt                2658
_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 SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_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)+(0.0567P)²+1.4406P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3513
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1212
_refine_ls_wR_factor_gt          0.1124
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
Cl1 Cl 0.32688(3) 0.38900(10) 1.06986(3) 0.0650(2) Uani 1 1 d . . . . .
F1 F 0.33782(7) 0.27499(19) 0.79317(5) 0.0591(4) Uani 1 1 d . . . . .
F2 F 0.32307(8) 0.4342(2) 0.85983(7) 0.0702(5) Uani 1 1 d . . . . .
F3 F 0.41916(7) 0.39816(18) 0.85789(6) 0.0600(4) Uani 1 1 d . . . . .
N1 N 0.51505(9) 0.1883(3) 0.95615(9) 0.0419(5) Uani 1 1 d . . . . .
O1 O 0.41366(6) 0.03987(19) 0.87197(6) 0.0391(4) Uani 1 1 d . . . . .
O2 O 0.31296(9) -0.3233(3) 0.74215(8) 0.0703(6) Uani 1 1 d . . . . .
O3 O 0.61446(8) 0.2539(3) 1.02421(7) 0.0609(5) Uani 1 1 d . . . . .
C1 C 0.47084(10) 0.2333(3) 0.98392(9) 0.0364(5) Uani 1 1 d . . . . .
C2 C 0.49213(12) 0.2995(3) 1.04093(9) 0.0447(6) Uani 1 1 d . . . . .
H2 H 0.5367 0.3119 1.0614 0.054 Uiso 1 1 calc R U . . .
C3 C 0.44876(12) 0.3467(3) 1.06743(10) 0.0474(6) Uani 1 1 d . . . . .
H3 H 0.4638 0.3916 1.1054 0.057 Uiso 1 1 calc R U . . .
C4 C 0.38269(11) 0.3276(3) 1.03751(9) 0.0432(6) Uani 1 1 d . . . . .
C5 C 0.36052(11) 0.2613(3) 0.98150(9) 0.0410(5) Uani 1 1 d . . . . .
H5 H 0.3158 0.2484 0.9619 0.049 Uiso 1 1 calc R U . . .
C6 C 0.40320(10) 0.2132(3) 0.95348(9) 0.0349(5) Uani 1 1 d . . . . .
C7 C 0.37161(10) 0.1560(3) 0.88950(9) 0.0356(5) Uani 1 1 d . . . . .
C8 C 0.30774(10) 0.0533(3) 0.87502(9) 0.0420(5) Uani 1 1 d . . . . .
H8A H 0.3061 -0.0081 0.9094 0.050 Uiso 1 1 calc R U . . .
H8B H 0.2704 0.1313 0.8606 0.050 Uiso 1 1 calc R U . . .
C9 C 0.30870(11) -0.0761(3) 0.82765(10) 0.0469(6) Uani 1 1 d . . . . .
H9A H 0.2946 -0.1918 0.8351 0.056 Uiso 1 1 calc R U . . .
H9B H 0.2803 -0.0367 0.7892 0.056 Uiso 1 1 calc R U . . .
C10 C 0.37756(10) -0.0800(3) 0.83113(9) 0.0373(5) Uani 1 1 d . . . . .
C11 C 0.40684(11) -0.1762(3) 0.80232(9) 0.0429(6) Uani 1 1 d . . . . .
H11 H 0.4515 -0.1629 0.8111 0.052 Uiso 1 1 calc R U . . .
C12 C 0.37114(13) -0.3031(3) 0.75707(10) 0.0489(6) Uani 1 1 d . . . . .
C13 C 0.41033(15) -0.4081(4) 0.72989(12) 0.0771(9) Uani 1 1 d . . . . .
H13A H 0.3826 -0.4925 0.7033 0.116 Uiso 1 1 calc R U . . .
H13B H 0.4445 -0.4684 0.7601 0.116 Uiso 1 1 calc R U . . .
H13C H 0.4291 -0.3313 0.7088 0.116 Uiso 1 1 calc R U . . .
C14 C 0.36250(11) 0.3175(3) 0.84969(10) 0.0445(6) Uani 1 1 d . . . . .
C15 C 0.58130(11) 0.2058(3) 0.97519(10) 0.0420(5) Uani 1 1 d . . . . .
C16 C 0.61096(11) 0.1594(3) 0.93013(10) 0.0427(5) Uani 1 1 d . . . . .
C17 C 0.57639(13) 0.1493(4) 0.87053(11) 0.0592(7) Uani 1 1 d . . . . .
H17 H 0.5315 0.1684 0.8565 0.071 Uiso 1 1 calc R U . . .
C18 C 0.60771(15) 0.1111(4) 0.83149(13) 0.0718(8) Uani 1 1 d . . . . .
H18 H 0.5839 0.1033 0.7915 0.086 Uiso 1 1 calc R U . . .
C19 C 0.67390(15) 0.0847(4) 0.85182(14) 0.0716(8) Uani 1 1 d . . . . .
H19 H 0.6951 0.0595 0.8256 0.086 Uiso 1 1 calc R U . . .
C20 C 0.70873(14) 0.0953(4) 0.91059(14) 0.0677(8) Uani 1 1 d . . . . .
H20 H 0.7537 0.0775 0.9243 0.081 Uiso 1 1 calc R U . . .
C21 C 0.67778(11) 0.1323(3) 0.94955(12) 0.0526(6) Uani 1 1 d . . . . .
H21 H 0.7020 0.1391 0.9895 0.063 Uiso 1 1 calc R U . . .
H1 H 0.4963(11) 0.140(3) 0.9226(10) 0.040(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.733(2) . ?
F1 C14 1.327(3) . ?
F2 C14 1.320(3) . ?
F3 C14 1.333(3) . ?
N1 C15 1.364(3) . ?
N1 C1 1.403(3) . ?
N1 H1 0.86(2) . ?
O1 C10 1.374(2) . ?
O1 C7 1.443(2) . ?
O2 C12 1.204(3) . ?
O3 C15 1.213(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.410(3) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(3) . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.526(3) . ?
C7 C8 1.529(3) . ?
C7 C14 1.532(3) . ?
C8 C9 1.521(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.479(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.324(3) . ?
C11 C12 1.465(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.486(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 C16 1.499(3) . ?
C16 C17 1.381(3) . ?
C16 C21 1.384(3) . ?
C17 C18 1.383(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.373(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?

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
C15 N1 C1 130.0(2) . . ?
C15 N1 H1 117.5(15) . . ?
C1 N1 H1 112.5(15) . . ?
C10 O1 C7 110.82(15) . . ?
C2 C1 N1 121.4(2) . . ?
C2 C1 C6 118.9(2) . . ?
N1 C1 C6 119.63(19) . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 119.7(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.1(2) . . ?
C5 C4 Cl1 119.37(18) . . ?
C3 C4 Cl1 120.48(18) . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.52(19) . . ?
C5 C6 C7 115.77(18) . . ?
C1 C6 C7 125.5(2) . . ?
O1 C7 C6 111.60(16) . . ?
O1 C7 C8 104.17(17) . . ?
C6 C7 C8 115.43(18) . . ?
O1 C7 C14 104.98(17) . . ?
C6 C7 C14 109.10(18) . . ?
C8 C7 C14 110.99(17) . . ?
C9 C8 C7 104.48(18) . . ?
C9 C8 H8A 110.9 . . ?
C7 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 C8 104.75(18) . . ?
C10 C9 H9A 110.8 . . ?
C8 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C11 C10 O1 119.15(19) . . ?
C11 C10 C9 130.8(2) . . ?
O1 C10 C9 110.05(18) . . ?
C10 C11 C12 122.1(2) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 H11 118.9 . . ?
O2 C12 C11 122.6(2) . . ?
O2 C12 C13 120.7(2) . . ?
C11 C12 C13 116.7(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
F2 C14 F1 107.62(19) . . ?
F2 C14 F3 107.3(2) . . ?
F1 C14 F3 106.56(19) . . ?
F2 C14 C7 111.65(19) . . ?
F1 C14 C7 111.96(19) . . ?
F3 C14 C7 111.50(18) . . ?
O3 C15 N1 124.0(2) . . ?
O3 C15 C16 121.7(2) . . ?
N1 C15 C16 114.24(19) . . ?
C17 C16 C21 118.2(2) . . ?
C17 C16 C15 124.2(2) . . ?
C21 C16 C15 117.5(2) . . ?
C16 C17 C18 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 C1 C2 -3.5(4) . . . . ?
C15 N1 C1 C6 175.7(2) . . . . ?
N1 C1 C2 C3 178.6(2) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C2 C3 C4 Cl1 -179.22(18) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
Cl1 C4 C5 C6 178.90(17) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 -175.1(2) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
N1 C1 C6 C5 -178.92(19) . . . . ?
C2 C1 C6 C7 175.1(2) . . . . ?
N1 C1 C6 C7 -4.2(3) . . . . ?
C10 O1 C7 C6 147.55(17) . . . . ?
C10 O1 C7 C8 22.4(2) . . . . ?
C10 O1 C7 C14 -94.39(19) . . . . ?
C5 C6 C7 O1 -154.68(18) . . . . ?
C1 C6 C7 O1 30.5(3) . . . . ?
C5 C6 C7 C8 -36.0(3) . . . . ?
C1 C6 C7 C8 149.1(2) . . . . ?
C5 C6 C7 C14 89.8(2) . . . . ?
C1 C6 C7 C14 -85.1(2) . . . . ?
O1 C7 C8 C9 -23.5(2) . . . . ?
C6 C7 C8 C9 -146.22(19) . . . . ?
C14 C7 C8 C9 89.0(2) . . . . ?
C7 C8 C9 C10 16.9(2) . . . . ?
C7 O1 C10 C11 168.05(19) . . . . ?
C7 O1 C10 C9 -11.9(2) . . . . ?
C8 C9 C10 C11 176.1(2) . . . . ?
C8 C9 C10 O1 -3.9(2) . . . . ?
O1 C10 C11 C12 -178.3(2) . . . . ?
C9 C10 C11 C12 1.7(4) . . . . ?
C10 C11 C12 O2 2.4(4) . . . . ?
C10 C11 C12 C13 -177.5(2) . . . . ?
O1 C7 C14 F2 178.20(17) . . . . ?
C6 C7 C14 F2 -62.1(2) . . . . ?
C8 C7 C14 F2 66.2(2) . . . . ?
O1 C7 C14 F1 57.4(2) . . . . ?
C6 C7 C14 F1 177.18(18) . . . . ?
C8 C7 C14 F1 -54.5(2) . . . . ?
O1 C7 C14 F3 -61.8(2) . . . . ?
C6 C7 C14 F3 57.9(2) . . . . ?
C8 C7 C14 F3 -173.81(18) . . . . ?
C1 N1 C15 O3 6.2(4) . . . . ?
C1 N1 C15 C16 -174.0(2) . . . . ?
O3 C15 C16 C17 -162.1(2) . . . . ?
N1 C15 C16 C17 18.1(3) . . . . ?
O3 C15 C16 C21 15.1(3) . . . . ?
N1 C15 C16 C21 -164.7(2) . . . . ?
C21 C16 C17 C18 0.7(4) . . . . ?
C15 C16 C17 C18 177.9(3) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C17 C18 C19 C20 0.3(5) . . . . ?
C18 C19 C20 C21 0.1(5) . . . . ?
C19 C20 C21 C16 0.0(4) . . . . ?
C17 C16 C21 C20 -0.4(4) . . . . ?
C15 C16 C21 C20 -177.7(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
N1 H1 O1 0.86(2) 1.95(2) 2.681(2) 143(2) .
C9 H9B O2 0.97 2.51 3.237(3) 132.0 4_556
C8 H8B O2 0.97 2.54 3.267(3) 131.3 4_556
C2 H2 O3 0.93 2.23 2.865(3) 124.5 .

_refine_diff_density_max         0.228
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-4



