# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_dan8956
_database_code_depnum_ccdc_archive 'CCDC 1855494'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H11 Cl F5 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         287.62

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5790(5)
_cell_length_b                   10.2974(4)
_cell_length_c                   9.8109(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.426(2)
_cell_angle_gamma                90
_cell_volume                     1103.19(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5379
_cell_measurement_theta_min      4.0484
_cell_measurement_theta_max      66.8042
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584

_exptl_absorpt_coefficient_mu    3.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.86

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            14163
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_theta_min         4.05
_diffrn_reflns_theta_max         66.80
_diffrn_reflns_theta_full        66.80
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_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.
;

_reflns_number_total             1940
_reflns_number_gt                1700
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0735
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_number_reflns         1940
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+0.4753P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.237
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.12017(4) 0.32393(4) 0.51492(5) 0.01672(14) Uani d . . . 1 . .
N N1 0.12732(15) 0.95513(16) 0.23026(18) 0.0156(3) Uani d . . . 1 . .
H H1A 0.103(2) 1.017(2) 0.163(3) 0.023(6) Uiso d . . . 1 . .
H H1B 0.064(2) 0.923(2) 0.248(2) 0.021(6) Uiso d . . . 1 . .
O O1 0.10205(12) 0.70731(13) 0.31089(14) 0.0191(3) Uani d . . . 1 . .
O O2 0.17230(13) 0.62229(14) 0.14308(16) 0.0218(3) Uani d . . . 1 . .
H H2A 0.151(3) 0.549(3) 0.171(3) 0.042(8) Uiso d . . . 1 . .
O O3 0.09952(13) 0.40489(14) 0.20912(18) 0.0193(3) Uani d . . . 1 . .
H H3A 0.101(2) 0.349(3) 0.158(3) 0.033(8) Uiso d . . . 1 . .
H H3B 0.127(2) 0.379(2) 0.296(3) 0.029(7) Uiso d . . . 1 . .
F F1 0.35710(11) 0.93612(12) 0.02848(12) 0.0258(3) Uani d . . . 1 . .
F F2 0.38150(10) 0.73156(11) 0.08580(12) 0.0230(3) Uani d . . . 1 . .
F F3 0.56315(11) 0.99738(13) 0.24042(17) 0.0400(4) Uani d . . . 1 . .
F F4 0.57914(11) 0.80435(14) 0.33063(14) 0.0368(3) Uani d . . . 1 . .
F F5 0.59352(11) 0.83432(12) 0.11990(14) 0.0300(3) Uani d . . . 1 . .
C C2 0.18598(17) 0.84783(18) 0.1729(2) 0.0146(4) Uani d . . . 1 . .
H H2 0.1626 0.8539 0.0654 0.018 Uiso calc U . R 1 . .
C C3 0.32646(16) 0.86959(18) 0.2462(2) 0.0147(4) Uani d . . . 1 . .
H H3 0.3579 0.8045 0.3256 0.018 Uiso calc U . R 1 . .
C C4 0.33682(17) 1.00573(19) 0.3142(2) 0.0187(4) Uani d . . . 1 . .
H H4A 0.4122 1.0139 0.3991 0.022 Uiso calc U . R 1 . .
H H4B 0.3365 1.0742 0.2432 0.022 Uiso calc U . R 1 . .
C C5 0.22327(18) 1.01358(19) 0.3581(2) 0.0194(4) Uani d . . . 1 . .
H H5A 0.2334 0.9629 0.4471 0.023 Uiso calc U . R 1 . .
H H5B 0.2033 1.1047 0.3736 0.023 Uiso calc U . R 1 . .
C C6 0.14677(16) 0.71789(18) 0.2167(2) 0.0141(4) Uani d . . . 1 . .
C C7 0.39661(17) 0.85372(18) 0.1421(2) 0.0159(4) Uani d . . . 1 . .
C C8 0.53617(18) 0.8733(2) 0.2091(2) 0.0230(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 . 1.498(3) ?
N1 C2 . 1.501(2) ?
N1 H1A . 0.89(3) ?
N1 H1B . 0.87(3) ?
O1 C6 . 1.205(2) ?
O2 C6 . 1.312(2) ?
O2 H2A . 0.87(3) ?
O3 H3A . 0.77(3) ?
O3 H3B . 0.85(3) ?
F1 C7 . 1.354(2) ?
F2 C7 . 1.362(2) ?
F3 C8 . 1.327(2) ?
F4 C8 . 1.333(3) ?
F5 C8 . 1.325(2) ?
C2 C6 . 1.520(3) ?
C2 C3 . 1.560(2) ?
C2 H2 . 1.0 ?
C3 C7 . 1.510(3) ?
C3 C4 . 1.540(3) ?
C3 H3 . 1.0 ?
C4 C5 . 1.516(3) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C7 C8 . 1.542(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C2 . . 107.92(15) ?
C5 N1 H1A . . 107.4(15) ?
C2 N1 H1A . . 108.8(15) ?
C5 N1 H1B . . 114.8(15) ?
C2 N1 H1B . . 108.3(15) ?
H1A N1 H1B . . 110.(2) ?
C6 O2 H2A . . 110.1(19) ?
H3A O3 H3B . . 110.(3) ?
N1 C2 C6 . . 109.08(15) ?
N1 C2 C3 . . 104.71(14) ?
C6 C2 C3 . . 111.08(15) ?
N1 C2 H2 . . 110.6 ?
C6 C2 H2 . . 110.6 ?
C3 C2 H2 . . 110.6 ?
C7 C3 C4 . . 114.17(15) ?
C7 C3 C2 . . 112.70(15) ?
C4 C3 C2 . . 104.43(15) ?
C7 C3 H3 . . 108.4 ?
C4 C3 H3 . . 108.4 ?
C2 C3 H3 . . 108.4 ?
C5 C4 C3 . . 102.82(15) ?
C5 C4 H4A . . 111.2 ?
C3 C4 H4A . . 111.2 ?
C5 C4 H4B . . 111.2 ?
C3 C4 H4B . . 111.2 ?
H4A C4 H4B . . 109.1 ?
N1 C5 C4 . . 102.26(15) ?
N1 C5 H5A . . 111.3 ?
C4 C5 H5A . . 111.3 ?
N1 C5 H5B . . 111.3 ?
C4 C5 H5B . . 111.3 ?
H5A C5 H5B . . 109.2 ?
O1 C6 O2 . . 125.98(17) ?
O1 C6 C2 . . 122.77(17) ?
O2 C6 C2 . . 111.20(16) ?
F1 C7 F2 . . 106.38(15) ?
F1 C7 C3 . . 112.24(15) ?
F2 C7 C3 . . 110.43(15) ?
F1 C7 C8 . . 106.75(15) ?
F2 C7 C8 . . 105.59(15) ?
C3 C7 C8 . . 114.89(16) ?
F5 C8 F3 . . 108.26(17) ?
F5 C8 F4 . . 108.02(17) ?
F3 C8 F4 . . 108.47(18) ?
F5 C8 C7 . . 111.31(17) ?
F3 C8 C7 . . 110.93(16) ?
F4 C8 C7 . . 109.76(17) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C2 C6 . . . . 104.46(17) ?
C5 N1 C2 C3 . . . . -14.51(19) ?
N1 C2 C3 C7 . . . . -136.51(16) ?
C6 C2 C3 C7 . . . . 105.88(18) ?
N1 C2 C3 C4 . . . . -12.04(19) ?
C6 C2 C3 C4 . . . . -129.65(16) ?
C7 C3 C4 C5 . . . . 157.13(16) ?
C2 C3 C4 C5 . . . . 33.61(18) ?
C2 N1 C5 C4 . . . . 35.74(19) ?
C3 C4 C5 N1 . . . . -42.28(18) ?
N1 C2 C6 O1 . . . . -16.6(2) ?
C3 C2 C6 O1 . . . . 98.3(2) ?
N1 C2 C6 O2 . . . . 165.68(15) ?
C3 C2 C6 O2 . . . . -79.40(19) ?
C4 C3 C7 F1 . . . . -60.8(2) ?
C2 C3 C7 F1 . . . . 58.2(2) ?
C4 C3 C7 F2 . . . . -179.28(14) ?
C2 C3 C7 F2 . . . . -60.34(19) ?
C4 C3 C7 C8 . . . . 61.4(2) ?
C2 C3 C7 C8 . . . . -179.62(16) ?
F1 C7 C8 F5 . . . . -66.7(2) ?
F2 C7 C8 F5 . . . . 46.2(2) ?
C3 C7 C8 F5 . . . . 168.17(16) ?
F1 C7 C8 F3 . . . . 53.9(2) ?
F2 C7 C8 F3 . . . . 166.85(16) ?
C3 C7 C8 F3 . . . . -71.2(2) ?
F1 C7 C8 F4 . . . . 173.76(15) ?
F2 C7 C8 F4 . . . . -73.30(19) ?
C3 C7 C8 F4 . . . . 48.6(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A Cl1 4_575 0.89(3) 2.24(3) 3.0871(18) 157.(2) ?
N1 H1B O3 2 0.87(3) 2.08(3) 2.926(2) 163.(2) ?
O2 H2A O3 . 0.87(3) 1.68(3) 2.5505(19) 174.(3) ?
O3 H3A Cl1 4_565 0.77(3) 2.32(3) 3.0891(17) 176.(3) ?
O3 H3B Cl1 . 0.85(3) 2.24(3) 3.0456(17) 157.(2) ?
C2 H2 O1 4_575 1.0 2.44 3.404(2) 161.4 ?
C3 H3 F2 4_576 1.0 2.5 3.344(2) 141.5 ?
C5 H5A O2 4_576 0.99 2.42 3.350(2) 155.6 ?
C5 H5B Cl1 1_565 0.99 2.97 3.902(2) 156.9 ?

####################################################################### 
# 
# 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_haf8893
_database_code_depnum_ccdc_archive 'CCDC 1855498'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H20 Cl F2 N O5'
_chemical_formula_weight         343.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   19.3791(4)
_cell_length_b                   9.2260(2)
_cell_length_c                   19.4047(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.3220(10)
_cell_angle_gamma                90.00
_cell_volume                     3346.08(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7691
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    0.269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9407
_exptl_absorpt_correction_T_max  0.9893
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21562
_diffrn_reflns_av_R_equivalents  0.050
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.11
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5760
_reflns_number_gt                4993
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XP-SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1672P)²+6.1313P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5760
_refine_ls_number_parameters     408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0866
_refine_ls_wR_factor_ref         0.2717
_refine_ls_wR_factor_gt          0.2572
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.8878(3) 0.6701(5) 0.2031(3) 0.0380(11) Uani 1 1 d . . .
C2 C 0.9122(3) 0.6095(6) 0.2747(3) 0.0314(12) Uani 1 1 d . . .
H2 H 0.9505 0.5360 0.2761 0.038 Uiso 1 1 calc R . .
C3 C 0.9452(3) 0.7460(6) 0.3191(3) 0.0357(13) Uani 1 1 d . . .
C4 C 0.8961(3) 0.8693(7) 0.2788(4) 0.0417(14) Uani 1 1 d . . .
H4A H 0.8499 0.8714 0.2917 0.050 Uiso 1 1 calc R . .
H4B H 0.9196 0.9650 0.2895 0.050 Uiso 1 1 calc R . .
C5 C 0.8854(3) 0.8289(6) 0.2011(3) 0.0372(13) Uani 1 1 d . . .
H5A H 0.8388 0.8642 0.1714 0.045 Uiso 1 1 calc R . .
H5B H 0.9242 0.8689 0.1821 0.045 Uiso 1 1 calc R . .
O1 O 0.8307(3) 0.6373(5) 0.0858(2) 0.0451(11) Uani 1 1 d . . .
O2 O 0.8650(2) 0.4468(4) 0.1619(2) 0.0391(10) Uani 1 1 d . . .
O3 O 0.7887(2) 0.5795(6) 0.2755(3) 0.0545(13) Uani 1 1 d . . .
O4 O 0.8714(2) 0.4283(5) 0.3388(3) 0.0484(11) Uani 1 1 d . . .
O5 O 1.0136(2) 0.7710(5) 0.3099(2) 0.0405(10) Uani 1 1 d . . .
H5 H 1.0397 0.6986 0.3243 0.061 Uiso 1 1 calc R . .
C6 C 0.9496(4) 0.7391(8) 0.3983(3) 0.0445(15) Uani 1 1 d . . .
F1 F 0.8850(2) 0.7180(6) 0.4105(2) 0.0675(13) Uani 1 1 d . . .
F2 F 0.9814(2) 0.8872(3) 0.43989(17) 0.0371(8) Uani 1 1 d . . .
Cl1 Cl 1.00088(18) 0.6176(3) 0.44191(18) 0.0956(9) Uani 1 1 d . . .
C7 C 0.8590(3) 0.5881(6) 0.1453(3) 0.0346(12) Uani 1 1 d . . .
C8 C 0.8423(3) 0.3364(6) 0.1042(4) 0.0394(14) Uani 1 1 d . . .
C9 C 0.7627(4) 0.3463(9) 0.0725(5) 0.062(2) Uani 1 1 d . . .
H9A H 0.7390 0.3614 0.1108 0.094 Uiso 1 1 calc R . .
H9B H 0.7453 0.2562 0.0471 0.094 Uiso 1 1 calc R . .
H9C H 0.7519 0.4279 0.0390 0.094 Uiso 1 1 calc R . .
C10 C 0.8851(5) 0.3492(9) 0.0518(5) 0.068(2) Uani 1 1 d . . .
H10A H 0.9358 0.3602 0.0771 0.101 Uiso 1 1 calc R . .
H10B H 0.8692 0.4342 0.0214 0.101 Uiso 1 1 calc R . .
H10C H 0.8788 0.2619 0.0220 0.101 Uiso 1 1 calc R . .
C11 C 0.8596(5) 0.1960(7) 0.1476(5) 0.060(2) Uani 1 1 d . . .
H11A H 0.8342 0.1952 0.1850 0.090 Uiso 1 1 calc R . .
H11B H 0.9112 0.1903 0.1695 0.090 Uiso 1 1 calc R . .
H11C H 0.8444 0.1126 0.1159 0.090 Uiso 1 1 calc R . .
C12 C 0.8497(3) 0.5391(7) 0.2970(3) 0.0419(14) Uani 1 1 d . . .
C13 C 0.8156(4) 0.3485(9) 0.3618(5) 0.064(2) Uani 1 1 d . . .
H13A H 0.7942 0.4116 0.3919 0.077 Uiso 1 1 calc R . .
H13B H 0.7772 0.3184 0.3196 0.077 Uiso 1 1 calc R . .
C14 C 0.8476(5) 0.2220(12) 0.4021(7) 0.091(3) Uani 1 1 d . . .
H14A H 0.8911 0.2507 0.4382 0.137 Uiso 1 1 calc R . .
H14B H 0.8598 0.1510 0.3696 0.137 Uiso 1 1 calc R . .
H14C H 0.8136 0.1788 0.4255 0.137 Uiso 1 1 calc R . .
N1A N 0.7017(2) 0.9598(5) -0.1156(3) 0.0370(11) Uani 1 1 d . . .
C2A C 0.7716(3) 1.0244(6) -0.0901(3) 0.0348(13) Uani 1 1 d . . .
H2A H 0.7700 1.1008 -0.0540 0.042 Uiso 1 1 calc R . .
C3A C 0.8154(3) 0.8916(6) -0.0515(3) 0.0333(12) Uani 1 1 d . . .
C4A C 0.7808(3) 0.7630(7) -0.0956(4) 0.0411(15) Uani 1 1 d . . .
H401 H 0.7914 0.6717 -0.0681 0.049 Uiso 1 1 calc R . .
H402 H 0.7966 0.7540 -0.1399 0.049 Uiso 1 1 calc R . .
C5A C 0.7014(3) 0.8012(6) -0.1121(3) 0.0387(13) Uani 1 1 d . . .
H501 H 0.6744 0.7587 -0.1582 0.046 Uiso 1 1 calc R . .
H502 H 0.6803 0.7668 -0.0738 0.046 Uiso 1 1 calc R . .
O1A O 0.5841(2) 0.9850(5) -0.1720(3) 0.0462(11) Uani 1 1 d . . .
O2A O 0.6586(2) 1.1795(4) -0.1388(2) 0.0421(10) Uani 1 1 d . . .
O3A O 0.7754(3) 1.0509(6) -0.2132(3) 0.0585(13) Uani 1 1 d . . .
O4A O 0.8368(2) 1.2057(5) -0.1295(2) 0.0438(10) Uani 1 1 d . . .
O5A O 0.8052(2) 0.8933(4) 0.0174(2) 0.0375(9) Uani 1 1 d . . .
H5C H 0.8136 0.8106 0.0357 0.056 Uiso 1 1 calc R . .
C6A C 0.8958(3) 0.9049(7) -0.0453(4) 0.0451(15) Uani 1 1 d . . .
F1A F 0.9098(2) 0.9198(5) -0.1088(2) 0.0593(11) Uani 1 1 d . . .
F2A F 0.92351(19) 1.0210(4) -0.0059(2) 0.0506(10) Uani 1 1 d . . .
Cl1A Cl 0.94254(9) 0.7497(2) -0.00371(14) 0.0664(6) Uani 1 1 d . . .
C7A C 0.6431(3) 1.0390(6) -0.1446(3) 0.0366(13) Uani 1 1 d . . .
C8A C 0.6025(3) 1.2915(6) -0.1624(4) 0.0396(14) Uani 1 1 d . . .
C9A C 0.6435(4) 1.4313(8) -0.1433(5) 0.061(2) Uani 1 1 d . . .
H901 H 0.6636 1.4365 -0.0914 0.091 Uiso 1 1 calc R . .
H902 H 0.6113 1.5136 -0.1593 0.091 Uiso 1 1 calc R . .
H903 H 0.6824 1.4347 -0.1669 0.091 Uiso 1 1 calc R . .
C10A C 0.5711(5) 1.2809(11) -0.2429(5) 0.072(2) Uani 1 1 d . . .
H10D H 0.5365 1.2011 -0.2538 0.108 Uiso 1 1 calc R . .
H10E H 0.6096 1.2627 -0.2660 0.108 Uiso 1 1 calc R . .
H10F H 0.5470 1.3720 -0.2609 0.108 Uiso 1 1 calc R . .
C11A C 0.5473(5) 1.2729(9) -0.1200(6) 0.074(3) Uani 1 1 d . . .
H11D H 0.5161 1.1906 -0.1391 0.110 Uiso 1 1 calc R . .
H11E H 0.5184 1.3612 -0.1238 0.110 Uiso 1 1 calc R . .
H11F H 0.5718 1.2548 -0.0697 0.110 Uiso 1 1 calc R . .
C12A C 0.7952(3) 1.0926(7) -0.1522(3) 0.0400(14) Uani 1 1 d . . .
C13A C 0.8629(5) 1.2827(10) -0.1841(4) 0.065(2) Uani 1 1 d . . .
H13C H 0.8915 1.2165 -0.2057 0.078 Uiso 1 1 calc R . .
H13D H 0.8220 1.3190 -0.2224 0.078 Uiso 1 1 calc R . .
C14A C 0.9069(7) 1.4036(11) -0.1488(5) 0.093(4) Uani 1 1 d . . .
H14D H 0.9481 1.3661 -0.1122 0.139 Uiso 1 1 calc R . .
H14E H 0.8785 1.4665 -0.1262 0.139 Uiso 1 1 calc R . .
H14F H 0.9238 1.4593 -0.1841 0.139 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.347(8) . ?
N1 C2 1.454(7) . ?
N1 C5 1.467(7) . ?
C2 C12 1.534(8) . ?
C2 C3 1.564(8) . ?
C2 H2 1.0000 . ?
C3 O5 1.404(7) . ?
C3 C6 1.517(9) . ?
C3 C4 1.554(8) . ?
C4 C5 1.514(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
O1 C7 1.227(7) . ?
O2 C7 1.341(7) . ?
O2 C8 1.490(7) . ?
O3 C12 1.205(8) . ?
O4 C12 1.303(8) . ?
O4 C13 1.472(8) . ?
O5 H5 0.8400 . ?
C6 F1 1.349(9) . ?
C6 Cl1 1.586(7) . ?
C6 F2 1.623(7) . ?
C8 C10 1.479(11) . ?
C8 C9 1.506(9) . ?
C8 C11 1.532(9) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.450(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N1A C7A 1.343(8) . ?
N1A C2A 1.443(7) . ?
N1A C5A 1.465(8) . ?
C2A C12A 1.534(9) . ?
C2A C3A 1.563(8) . ?
C2A H2A 1.0000 . ?
C3A O5A 1.402(7) . ?
C3A C4A 1.512(8) . ?
C3A C6A 1.536(8) . ?
C4A C5A 1.527(9) . ?
C4A H401 0.9900 . ?
C4A H402 0.9900 . ?
C5A H501 0.9900 . ?
C5A H502 0.9900 . ?
O1A C7A 1.231(7) . ?
O2A C7A 1.329(7) . ?
O2A C8A 1.482(7) . ?
O3A C12A 1.206(8) . ?
O4A C12A 1.320(7) . ?
O4A C13A 1.472(8) . ?
O5A H5C 0.8400 . ?
C6A F1A 1.338(9) . ?
C6A F2A 1.343(7) . ?
C6A Cl1A 1.771(7) . ?
C8A C9A 1.510(9) . ?
C8A C11A 1.522(10) . ?
C8A C10A 1.523(11) . ?
C9A H901 0.9800 . ?
C9A H902 0.9800 . ?
C9A H903 0.9800 . ?
C10A H10D 0.9800 . ?
C10A H10E 0.9800 . ?
C10A H10F 0.9800 . ?
C11A H11D 0.9800 . ?
C11A H11E 0.9800 . ?
C11A H11F 0.9800 . ?
C13A C14A 1.462(12) . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C2 122.6(5) . . ?
C7 N1 C5 122.4(5) . . ?
C2 N1 C5 114.2(5) . . ?
N1 C2 C12 110.5(5) . . ?
N1 C2 C3 101.5(4) . . ?
C12 C2 C3 115.0(5) . . ?
N1 C2 H2 109.8 . . ?
C12 C2 H2 109.8 . . ?
C3 C2 H2 109.8 . . ?
O5 C3 C6 109.5(5) . . ?
O5 C3 C4 106.8(5) . . ?
C6 C3 C4 113.8(5) . . ?
O5 C3 C2 108.9(5) . . ?
C6 C3 C2 115.5(5) . . ?
C4 C3 C2 101.9(5) . . ?
C5 C4 C3 103.0(5) . . ?
C5 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
N1 C5 C4 102.9(5) . . ?
N1 C5 H5A 111.2 . . ?
C4 C5 H5A 111.2 . . ?
N1 C5 H5B 111.2 . . ?
C4 C5 H5B 111.2 . . ?
H5A C5 H5B 109.1 . . ?
C7 O2 C8 119.6(4) . . ?
C12 O4 C13 116.1(5) . . ?
C3 O5 H5 109.5 . . ?
F1 C6 C3 112.1(5) . . ?
F1 C6 Cl1 106.5(5) . . ?
C3 C6 Cl1 115.5(5) . . ?
F1 C6 F2 106.4(5) . . ?
C3 C6 F2 112.4(5) . . ?
Cl1 C6 F2 103.1(4) . . ?
O1 C7 O2 125.1(5) . . ?
O1 C7 N1 124.1(5) . . ?
O2 C7 N1 110.8(5) . . ?
C10 C8 O2 110.7(5) . . ?
C10 C8 C9 114.5(7) . . ?
O2 C8 C9 109.4(5) . . ?
C10 C8 C11 111.4(7) . . ?
O2 C8 C11 100.8(5) . . ?
C9 C8 C11 109.1(6) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 125.7(6) . . ?
O3 C12 C2 123.1(6) . . ?
O4 C12 C2 111.1(5) . . ?
C14 C13 O4 108.8(7) . . ?
C14 C13 H13A 109.9 . . ?
O4 C13 H13A 109.9 . . ?
C14 C13 H13B 109.9 . . ?
O4 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7A N1A C2A 122.2(5) . . ?
C7A N1A C5A 123.4(5) . . ?
C2A N1A C5A 114.3(5) . . ?
N1A C2A C12A 110.4(5) . . ?
N1A C2A C3A 100.5(4) . . ?
C12A C2A C3A 117.5(5) . . ?
N1A C2A H2A 109.3 . . ?
C12A C2A H2A 109.4 . . ?
C3A C2A H2A 109.3 . . ?
O5A C3A C4A 113.3(5) . . ?
O5A C3A C6A 108.6(5) . . ?
C4A C3A C6A 113.4(5) . . ?
O5A C3A C2A 104.6(4) . . ?
C4A C3A C2A 103.9(5) . . ?
C6A C3A C2A 112.7(5) . . ?
C3A C4A C5A 102.1(5) . . ?
C3A C4A H401 111.4 . . ?
C5A C4A H401 111.4 . . ?
C3A C4A H402 111.4 . . ?
C5A C4A H402 111.4 . . ?
H401 C4A H402 109.2 . . ?
N1A C5A C4A 103.0(5) . . ?
N1A C5A H501 111.2 . . ?
C4A C5A H501 111.2 . . ?
N1A C5A H502 111.2 . . ?
C4A C5A H502 111.2 . . ?
H501 C5A H502 109.1 . . ?
C7A O2A C8A 121.5(5) . . ?
C12A O4A C13A 115.8(5) . . ?
C3A O5A H5C 109.5 . . ?
F1A C6A F2A 107.2(5) . . ?
F1A C6A C3A 112.6(5) . . ?
F2A C6A C3A 110.7(5) . . ?
F1A C6A Cl1A 107.4(5) . . ?
F2A C6A Cl1A 107.8(4) . . ?
C3A C6A Cl1A 110.9(4) . . ?
O1A C7A O2A 126.5(5) . . ?
O1A C7A N1A 123.1(5) . . ?
O2A C7A N1A 110.4(5) . . ?
O2A C8A C9A 102.9(5) . . ?
O2A C8A C11A 108.5(6) . . ?
C9A C8A C11A 111.4(7) . . ?
O2A C8A C10A 109.5(6) . . ?
C9A C8A C10A 110.4(7) . . ?
C11A C8A C10A 113.6(7) . . ?
C8A C9A H901 109.5 . . ?
C8A C9A H902 109.5 . . ?
H901 C9A H902 109.5 . . ?
C8A C9A H903 109.5 . . ?
H901 C9A H903 109.5 . . ?
H902 C9A H903 109.5 . . ?
C8A C10A H10D 109.5 . . ?
C8A C10A H10E 109.5 . . ?
H10D C10A H10E 109.5 . . ?
C8A C10A H10F 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C8A C11A H11D 109.5 . . ?
C8A C11A H11E 109.5 . . ?
H11D C11A H11E 109.5 . . ?
C8A C11A H11F 109.5 . . ?
H11D C11A H11F 109.5 . . ?
H11E C11A H11F 109.5 . . ?
O3A C12A O4A 126.0(6) . . ?
O3A C12A C2A 123.8(5) . . ?
O4A C12A C2A 110.1(5) . . ?
C14A C13A O4A 107.5(7) . . ?
C14A C13A H13C 110.2 . . ?
O4A C13A H13C 110.2 . . ?
C14A C13A H13D 110.2 . . ?
O4A C13A H13D 110.2 . . ?
H13C C13A H13D 108.5 . . ?
C13A C14A H14D 109.5 . . ?
C13A C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
C13A C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 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
C7 N1 C2 C12 -61.6(7) . . . . ?
C5 N1 C2 C12 108.1(6) . . . . ?
C7 N1 C2 C3 175.9(5) . . . . ?
C5 N1 C2 C3 -14.3(6) . . . . ?
N1 C2 C3 O5 -79.5(5) . . . . ?
C12 C2 C3 O5 161.2(5) . . . . ?
N1 C2 C3 C6 156.9(5) . . . . ?
C12 C2 C3 C6 37.6(7) . . . . ?
N1 C2 C3 C4 33.1(6) . . . . ?
C12 C2 C3 C4 -86.2(6) . . . . ?
O5 C3 C4 C5 73.3(6) . . . . ?
C6 C3 C4 C5 -165.7(5) . . . . ?
C2 C3 C4 C5 -40.8(6) . . . . ?
C7 N1 C5 C4 158.6(6) . . . . ?
C2 N1 C5 C4 -11.1(7) . . . . ?
C3 C4 C5 N1 31.9(6) . . . . ?
O5 C3 C6 F1 178.8(5) . . . . ?
C4 C3 C6 F1 59.4(7) . . . . ?
C2 C3 C6 F1 -57.9(7) . . . . ?
O5 C3 C6 Cl1 -58.9(6) . . . . ?
C4 C3 C6 Cl1 -178.3(5) . . . . ?
C2 C3 C6 Cl1 64.4(7) . . . . ?
O5 C3 C6 F2 59.1(6) . . . . ?
C4 C3 C6 F2 -60.4(7) . . . . ?
C2 C3 C6 F2 -177.7(4) . . . . ?
C8 O2 C7 O1 5.8(9) . . . . ?
C8 O2 C7 N1 -174.7(5) . . . . ?
C2 N1 C7 O1 171.5(6) . . . . ?
C5 N1 C7 O1 2.6(10) . . . . ?
C2 N1 C7 O2 -8.0(8) . . . . ?
C5 N1 C7 O2 -177.0(5) . . . . ?
C7 O2 C8 C10 61.4(7) . . . . ?
C7 O2 C8 C9 -65.7(8) . . . . ?
C7 O2 C8 C11 179.4(6) . . . . ?
C13 O4 C12 O3 -1.0(10) . . . . ?
C13 O4 C12 C2 -177.9(6) . . . . ?
N1 C2 C12 O3 -29.3(9) . . . . ?
C3 C2 C12 O3 84.8(8) . . . . ?
N1 C2 C12 O4 147.7(5) . . . . ?
C3 C2 C12 O4 -98.1(6) . . . . ?
C12 O4 C13 C14 174.8(8) . . . . ?
C7A N1A C2A C12A -64.3(7) . . . . ?
C5A N1A C2A C12A 111.2(6) . . . . ?
C7A N1A C2A C3A 171.0(6) . . . . ?
C5A N1A C2A C3A -13.5(7) . . . . ?
N1A C2A C3A O5A -85.8(5) . . . . ?
C12A C2A C3A O5A 154.6(5) . . . . ?
N1A C2A C3A C4A 33.3(6) . . . . ?
C12A C2A C3A C4A -86.4(6) . . . . ?
N1A C2A C3A C6A 156.4(5) . . . . ?
C12A C2A C3A C6A 36.7(7) . . . . ?
O5A C3A C4A C5A 72.3(6) . . . . ?
C6A C3A C4A C5A -163.3(5) . . . . ?
C2A C3A C4A C5A -40.6(6) . . . . ?
C7A N1A C5A C4A 164.3(6) . . . . ?
C2A N1A C5A C4A -11.1(7) . . . . ?
C3A C4A C5A N1A 31.6(6) . . . . ?
O5A C3A C6A F1A -173.3(5) . . . . ?
C4A C3A C6A F1A 59.9(7) . . . . ?
C2A C3A C6A F1A -57.9(7) . . . . ?
O5A C3A C6A F2A -53.3(6) . . . . ?
C4A C3A C6A F2A 179.8(5) . . . . ?
C2A C3A C6A F2A 62.1(7) . . . . ?
O5A C3A C6A Cl1A 66.3(6) . . . . ?
C4A C3A C6A Cl1A -60.6(7) . . . . ?
C2A C3A C6A Cl1A -178.3(4) . . . . ?
C8A O2A C7A O1A 3.8(10) . . . . ?
C8A O2A C7A N1A -176.0(5) . . . . ?
C2A N1A C7A O1A 173.7(6) . . . . ?
C5A N1A C7A O1A -1.3(10) . . . . ?
C2A N1A C7A O2A -6.5(8) . . . . ?
C5A N1A C7A O2A 178.5(6) . . . . ?
C7A O2A C8A C9A 177.9(6) . . . . ?
C7A O2A C8A C11A 59.8(8) . . . . ?
C7A O2A C8A C10A -64.7(8) . . . . ?
C13A O4A C12A O3A -2.6(10) . . . . ?
C13A O4A C12A C2A -179.5(6) . . . . ?
N1A C2A C12A O3A -27.9(9) . . . . ?
C3A C2A C12A O3A 86.5(8) . . . . ?
N1A C2A C12A O4A 149.1(5) . . . . ?
C3A C2A C12A O4A -96.5(6) . . . . ?
C12A O4A C13A C14A 179.6(8) . . . . ?

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
O5A H5C O1 0.84 1.85 2.691(6) 173.4 .
O5 H5 O1A 0.84 1.89 2.705(6) 162.1 4_676

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.103
####################################################################### 
# 
# 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_haf8943
_database_code_depnum_ccdc_archive 'CCDC 1855499'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H15.50 Cl2 F2 N O4.25'
_chemical_formula_iupac          ?
_chemical_formula_weight         302.61

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   32.3706(15)
_cell_length_b                   5.5808(3)
_cell_length_c                   32.0773(15)
_cell_angle_alpha                90
_cell_angle_beta                 113.0500(10)
_cell_angle_gamma                90
_cell_volume                     5332.2(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9849
_cell_measurement_theta_min      3.2886
_cell_measurement_theta_max      68.3400
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.120
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2504

_exptl_absorpt_coefficient_mu    4.702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.36
_exptl_absorpt_correction_T_max  0.60

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            33870
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         68.37
_diffrn_reflns_theta_full        68.37
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38

_refine_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.

Two ethoxy and one CF2Cl groups are disordered over two positions. 
Several restraints (SADI, SAME, ISOR and SIMU) were used in order
to improve refinement stability.
;

_reflns_number_total             4837
_reflns_number_gt                4616
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1386
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.092
_refine_ls_number_reflns         4837
_refine_ls_number_parameters     414
_refine_ls_number_restraints     148
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+27.6415P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.746
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1A 1.14623(4) 0.14023(15) 0.42988(3) 0.0451(3) Uani d . . . 1.0 . .
Cl Cl2A 0.96930(2) 0.29232(13) 0.29879(2) 0.02656(19) Uani d . . . 1.0 . .
N N1A 1.06869(8) 0.5513(4) 0.29360(8) 0.0215(5) Uani d . . D 1.0 . .
H H1A 1.0468(8) 0.650(5) 0.2889(10) 0.017(8) Uiso d . . D 1.0 . .
H H1B 1.0570(12) 0.442(6) 0.2734(10) 0.038(11) Uiso d . . D 1.0 . .
F F1A 1.20489(6) 0.3721(4) 0.41421(7) 0.0415(5) Uani d . . . 1.0 . .
F F2A 1.15571(7) 0.5877(3) 0.42884(6) 0.0344(4) Uani d . . . 1.0 . .
O O1A 1.13849(8) 0.2157(4) 0.33243(8) 0.0283(5) Uani d . . D 1.0 . .
H H1 1.1623(10) 0.234(8) 0.3268(14) 0.045(12) Uiso d . . D 1.0 . .
O O2A 1.05749(8) 0.8306(4) 0.35618(7) 0.0311(5) Uani d . . . 1.0 . .
O O4A 1.0 0.8871(5) 0.25 0.0241(6) Uani d T P DS 1.0 . .
H H4A 0.9897(12) 0.978(6) 0.2654(11) 0.034(10) Uiso d . . D 1.0 . .
C C2A 1.08147(10) 0.4478(5) 0.33989(10) 0.0234(6) Uani d . . . 1.0 . .
H H2A 1.0671 0.2877 0.3383 0.028 Uiso calc U . R 1.0 . .
C C3A 1.13287(10) 0.4211(5) 0.35502(10) 0.0219(6) Uani d . . . 1.0 . .
C C4A 1.14586(10) 0.6500(5) 0.33721(10) 0.0229(6) Uani d . . . 1.0 . .
H H401 1.1462 0.7892 0.3565 0.028 Uiso calc U . R 1.0 . .
H H402 1.1757 0.6342 0.3357 0.028 Uiso calc U . R 1.0 . .
C C5A 1.10897(10) 0.6745(5) 0.29016(10) 0.0262(6) Uani d . . . 1.0 . .
H H501 1.1024 0.8453 0.2819 0.031 Uiso calc U . R 1.0 . .
H H502 1.1177 0.5953 0.2672 0.031 Uiso calc U . R 1.0 . .
C C6A 1.15985(12) 0.3927(6) 0.40603(11) 0.0314(7) Uani d . . . 1.0 . .
C C7A 1.06579(10) 0.6241(6) 0.36689(10) 0.0266(7) Uani d . . . 1.0 . .
O O3A 1.06255(8) 0.5150(4) 0.40214(7) 0.0362(6) Uani d . . D 1.0 . .
C C8A 1.0490(3) 0.6697(13) 0.4317(3) 0.0443(19) Uani d U P D 0.87(3) A 1
H H831 1.0233 0.772 0.4135 0.053 Uiso calc U P R 0.87(3) A 1
H H832 1.0742 0.7739 0.4504 0.053 Uiso calc U P R 0.87(3) A 1
C C9A 1.0362(4) 0.5010(13) 0.4609(3) 0.067(3) Uani d U P D 0.87(3) A 1
H H931 1.0265 0.5929 0.4815 0.101 Uiso calc U P R 0.87(3) A 1
H H932 1.0621 0.4016 0.4785 0.101 Uiso calc U P R 0.87(3) A 1
H H933 1.0115 0.3981 0.4417 0.101 Uiso calc U P R 0.87(3) A 1
C C8C 1.052(2) 0.636(11) 0.438(2) 0.047(10) Uani d U P D 0.13(3) A 2
H H841 1.045 0.8063 0.4296 0.056 Uiso calc U P R 0.13(3) A 2
H H842 1.0788 0.6285 0.4669 0.056 Uiso calc U P R 0.13(3) A 2
C C9C 1.013(2) 0.510(11) 0.441(3) 0.081(14) Uani d U P D 0.13(3) A 2
H H941 1.0044 0.5934 0.4632 0.121 Uiso calc U P R 0.13(3) A 2
H H942 1.022 0.3447 0.4515 0.121 Uiso calc U P R 0.13(3) A 2
H H943 0.9884 0.5079 0.4116 0.121 Uiso calc U P R 0.13(3) A 2
Cl Cl2B 0.71187(3) 0.22536(16) 0.26346(3) 0.0375(2) Uani d . . . 1.0 . .
C C6B 0.88842(11) 0.0341(7) 0.42749(12) 0.0378(8) Uani d . . D 1.0 . .
Cl Cl1B 0.94617(4) -0.0282(3) 0.45136(4) 0.0620(4) Uani d U P D 0.934(3) B 1
F F1B 0.88181(11) 0.2476(5) 0.44417(11) 0.0418(7) Uani d U P D 0.934(3) B 1
F F2B 0.86714(12) -0.1475(4) 0.44556(16) 0.0503(8) Uani d U P D 0.934(3) B 1
Cl Cl1D 0.9383(5) 0.120(4) 0.4436(6) 0.0620(4) Uani d U P D 0.066(3) B 2
F F1D 0.8681(14) 0.212(6) 0.4453(19) 0.050(14) Uani d U P D 0.066(3) B 2
F F2D 0.8735(19) -0.183(5) 0.440(3) 0.0503(8) Uani d U P D 0.066(3) B 2
N N1B 0.81667(9) 0.1469(6) 0.30535(9) 0.0325(6) Uani d . . D 1.0 . .
H H1C 0.8106(15) 0.021(6) 0.2877(13) 0.052(13) Uiso d . . D 1.0 . .
H H1D 0.7950(12) 0.249(7) 0.2924(15) 0.066(15) Uiso d . . D 1.0 . .
O O1B 0.87977(8) -0.1812(4) 0.36069(9) 0.0322(5) Uani d . . D 1.0 . .
H H2 0.9047(9) -0.174(8) 0.3575(15) 0.052(13) Uiso d . . D 1.0 . .
O O2B 0.79939(9) 0.4856(4) 0.35649(9) 0.0414(6) Uani d . . . 1.0 . .
O O4B 0.70844(10) 0.7413(5) 0.30997(11) 0.0484(7) Uani d . . D 1.0 . .
H H4C 0.7198(14) 0.611(5) 0.3056(15) 0.048(12) Uiso d . . D 1.0 . .
H H4D 0.709(2) 0.870(7) 0.2952(17) 0.083(19) Uiso d . . D 1.0 . .
O O5B 0.95035(10) 0.7892(5) 0.33853(11) 0.0476(7) Uani d . . D 1.0 . .
H H5A 0.9596(15) 0.659(5) 0.3304(15) 0.054(13) Uiso d . . D 1.0 . .
H H5B 0.9596(14) 0.911(6) 0.3280(14) 0.050(12) Uiso d . . D 1.0 . .
C C2B 0.81986(10) 0.0786(6) 0.35151(11) 0.0271(7) Uani d . . . 1.0 . .
H H2B 0.8034 -0.0741 0.3506 0.033 Uiso calc U . R 1.0 . .
C C3B 0.87166(10) 0.0422(5) 0.37611(10) 0.0243(6) Uani d . . . 1.0 . .
C C4B 0.89053(10) 0.2487(5) 0.35841(10) 0.0250(6) Uani d . . . 1.0 . .
H H411 0.922 0.217 0.3625 0.03 Uiso calc U . R 1.0 . .
H H412 0.8894 0.4 0.374 0.03 Uiso calc U . R 1.0 . .
C C5B 0.86007(11) 0.2605(6) 0.30851(11) 0.0331(7) Uani d . . . 1.0 . .
H H511 0.8551 0.4287 0.2979 0.04 Uiso calc U . R 1.0 . .
H H512 0.8732 0.1708 0.29 0.04 Uiso calc U . R 1.0 . .
C C7B 0.80023(10) 0.2845(6) 0.36905(11) 0.0283(7) Uani d . . . 1.0 . .
O O3B 0.78400(9) 0.2083(5) 0.39859(9) 0.0398(6) Uani d . . D 1.0 . .
C C8B 0.7698(8) 0.408(3) 0.4208(6) 0.052(5) Uani d U P D 0.47(2) C 1
H H811 0.7377 0.4457 0.4035 0.062 Uiso calc U P R 0.47(2) C 1
H H812 0.7877 0.5533 0.4219 0.062 Uiso calc U P R 0.47(2) C 1
C C9B 0.7770(6) 0.331(3) 0.4677(4) 0.072(4) Uani d U P D 0.47(2) C 1
H H911 0.7625 0.446 0.4808 0.107 Uiso calc U P R 0.47(2) C 1
H H912 0.8093 0.3258 0.4864 0.107 Uiso calc U P R 0.47(2) C 1
H H913 0.764 0.1719 0.4668 0.107 Uiso calc U P R 0.47(2) C 1
C C8D 0.7614(5) 0.384(3) 0.4168(4) 0.033(3) Uani d U P D 0.53(2) C 2
H H821 0.7343 0.312 0.4188 0.04 Uiso calc U P R 0.53(2) C 2
H H822 0.7521 0.5259 0.3967 0.04 Uiso calc U P R 0.53(2) C 2
C C9D 0.7937(4) 0.455(3) 0.4625(3) 0.059(4) Uani d U P D 0.53(2) C 2
H H921 0.7794 0.5691 0.4759 0.088 Uiso calc U P R 0.53(2) C 2
H H922 0.82 0.5306 0.46 0.088 Uiso calc U P R 0.53(2) C 2
H H923 0.8032 0.3129 0.4818 0.088 Uiso calc U P R 0.53(2) C 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1A C6A . 1.740(3) ?
N1A C2A . 1.493(4) ?
N1A C5A . 1.516(4) ?
N1A H1A . 0.862(18) ?
N1A H1B . 0.861(19) ?
F1A C6A . 1.382(4) ?
F2A C6A . 1.347(4) ?
O1A C3A . 1.406(3) ?
O1A H1 . 0.863(19) ?
O2A C7A . 1.202(4) ?
O4A H4A . 0.861(18) ?
C2A C7A . 1.523(4) ?
C2A C3A . 1.547(4) ?
C2A H2A . 1.0 ?
C3A C4A . 1.524(4) ?
C3A C6A . 1.532(4) ?
C4A C5A . 1.520(4) ?
C4A H401 . 0.99 ?
C4A H402 . 0.99 ?
C5A H501 . 0.99 ?
C5A H502 . 0.99 ?
C7A O3A . 1.324(4) ?
O3A C8C . 1.466(19) ?
O3A C8A . 1.469(5) ?
C8A C9A . 1.497(8) ?
C8A H831 . 0.99 ?
C8A H832 . 0.99 ?
C9A H931 . 0.98 ?
C9A H932 . 0.98 ?
C9A H933 . 0.98 ?
C8C C9C . 1.49(2) ?
C8C H841 . 0.99 ?
C8C H842 . 0.99 ?
C9C H941 . 0.98 ?
C9C H942 . 0.98 ?
C9C H943 . 0.98 ?
C6B F1B . 1.357(5) ?
C6B F2D . 1.419(16) ?
C6B F1D . 1.429(16) ?
C6B F2B . 1.466(4) ?
C6B C3B . 1.521(5) ?
C6B Cl1D . 1.566(14) ?
C6B Cl1B . 1.755(4) ?
N1B C2B . 1.493(4) ?
N1B C5B . 1.508(4) ?
N1B H1C . 0.874(19) ?
N1B H1D . 0.87(2) ?
O1B C3B . 1.403(4) ?
O1B H2 . 0.851(19) ?
O2B C7B . 1.189(4) ?
O4B H4C . 0.853(19) ?
O4B H4D . 0.86(2) ?
O5B H5A . 0.865(19) ?
O5B H5B . 0.863(19) ?
C2B C7B . 1.523(4) ?
C2B C3B . 1.562(4) ?
C2B H2B . 1.0 ?
C3B C4B . 1.515(4) ?
C4B C5B . 1.517(4) ?
C4B H411 . 0.99 ?
C4B H412 . 0.99 ?
C5B H511 . 0.99 ?
C5B H512 . 0.99 ?
C7B O3B . 1.321(4) ?
O3B C8D . 1.474(9) ?
O3B C8B . 1.490(12) ?
C8B C9B . 1.491(16) ?
C8B H811 . 0.99 ?
C8B H812 . 0.99 ?
C9B H911 . 0.98 ?
C9B H912 . 0.98 ?
C9B H913 . 0.98 ?
C8D C9D . 1.485(13) ?
C8D H821 . 0.99 ?
C8D H822 . 0.99 ?
C9D H921 . 0.98 ?
C9D H922 . 0.98 ?
C9D H923 . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A N1A C5A . . 109.7(2) ?
C2A N1A H1A . . 108.(2) ?
C5A N1A H1A . . 112.(2) ?
C2A N1A H1B . . 110.(3) ?
C5A N1A H1B . . 114.(3) ?
H1A N1A H1B . . 103.(3) ?
C3A O1A H1 . . 108.(3) ?
N1A C2A C7A . . 106.9(2) ?
N1A C2A C3A . . 101.2(2) ?
C7A C2A C3A . . 116.1(2) ?
N1A C2A H2A . . 110.7 ?
C7A C2A H2A . . 110.7 ?
C3A C2A H2A . . 110.7 ?
O1A C3A C4A . . 112.3(2) ?
O1A C3A C6A . . 109.4(2) ?
C4A C3A C6A . . 111.2(2) ?
O1A C3A C2A . . 104.9(2) ?
C4A C3A C2A . . 102.9(2) ?
C6A C3A C2A . . 116.0(3) ?
C5A C4A C3A . . 102.9(2) ?
C5A C4A H401 . . 111.2 ?
C3A C4A H401 . . 111.2 ?
C5A C4A H402 . . 111.2 ?
C3A C4A H402 . . 111.2 ?
H401 C4A H402 . . 109.1 ?
N1A C5A C4A . . 104.5(2) ?
N1A C5A H501 . . 110.9 ?
C4A C5A H501 . . 110.9 ?
N1A C5A H502 . . 110.9 ?
C4A C5A H502 . . 110.9 ?
H501 C5A H502 . . 108.9 ?
F2A C6A F1A . . 106.6(3) ?
F2A C6A C3A . . 111.1(2) ?
F1A C6A C3A . . 109.2(3) ?
F2A C6A Cl1A . . 108.6(2) ?
F1A C6A Cl1A . . 106.2(2) ?
C3A C6A Cl1A . . 114.6(2) ?
O2A C7A O3A . . 127.0(3) ?
O2A C7A C2A . . 122.9(3) ?
O3A C7A C2A . . 110.1(3) ?
C7A O3A C8C . . 125.(3) ?
C7A O3A C8A . . 115.0(4) ?
O3A C8A C9A . . 105.0(5) ?
O3A C8A H831 . . 110.7 ?
C9A C8A H831 . . 110.7 ?
O3A C8A H832 . . 110.7 ?
C9A C8A H832 . . 110.7 ?
H831 C8A H832 . . 108.8 ?
C8A C9A H931 . . 109.5 ?
C8A C9A H932 . . 109.5 ?
H931 C9A H932 . . 109.5 ?
C8A C9A H933 . . 109.5 ?
H931 C9A H933 . . 109.5 ?
H932 C9A H933 . . 109.5 ?
O3A C8C C9C . . 107.(2) ?
O3A C8C H841 . . 110.3 ?
C9C C8C H841 . . 110.3 ?
O3A C8C H842 . . 110.3 ?
C9C C8C H842 . . 110.3 ?
H841 C8C H842 . . 108.5 ?
C8C C9C H941 . . 109.5 ?
C8C C9C H942 . . 109.5 ?
H941 C9C H942 . . 109.5 ?
C8C C9C H943 . . 109.5 ?
H941 C9C H943 . . 109.5 ?
H942 C9C H943 . . 109.5 ?
F2D C6B F1D . . 103.(2) ?
F1B C6B F2B . . 106.3(3) ?
F1B C6B C3B . . 110.9(3) ?
F2D C6B C3B . . 108.(3) ?
F1D C6B C3B . . 113.(2) ?
F2B C6B C3B . . 115.2(3) ?
F2D C6B Cl1D . . 126.(3) ?
F1D C6B Cl1D . . 103.3(17) ?
C3B C6B Cl1D . . 103.5(7) ?
F1B C6B Cl1B . . 107.9(3) ?
F2B C6B Cl1B . . 106.0(2) ?
C3B C6B Cl1B . . 110.2(2) ?
C2B N1B C5B . . 109.9(2) ?
C2B N1B H1C . . 110.(3) ?
C5B N1B H1C . . 110.(3) ?
C2B N1B H1D . . 112.(3) ?
C5B N1B H1D . . 108.(3) ?
H1C N1B H1D . . 106.(4) ?
C3B O1B H2 . . 108.(3) ?
H4C O4B H4D . . 121.(5) ?
H5A O5B H5B . . 109.(4) ?
N1B C2B C7B . . 107.3(3) ?
N1B C2B C3B . . 100.2(2) ?
C7B C2B C3B . . 115.6(3) ?
N1B C2B H2B . . 111.0 ?
C7B C2B H2B . . 111.0 ?
C3B C2B H2B . . 111.0 ?
O1B C3B C4B . . 112.6(2) ?
O1B C3B C6B . . 108.6(3) ?
C4B C3B C6B . . 113.8(3) ?
O1B C3B C2B . . 104.5(2) ?
C4B C3B C2B . . 102.8(2) ?
C6B C3B C2B . . 114.1(3) ?
C3B C4B C5B . . 103.7(2) ?
C3B C4B H411 . . 111.0 ?
C5B C4B H411 . . 111.0 ?
C3B C4B H412 . . 111.0 ?
C5B C4B H412 . . 111.0 ?
H411 C4B H412 . . 109.0 ?
N1B C5B C4B . . 104.8(3) ?
N1B C5B H511 . . 110.8 ?
C4B C5B H511 . . 110.8 ?
N1B C5B H512 . . 110.8 ?
C4B C5B H512 . . 110.8 ?
H511 C5B H512 . . 108.9 ?
O2B C7B O3B . . 125.7(3) ?
O2B C7B C2B . . 123.0(3) ?
O3B C7B C2B . . 111.3(3) ?
C7B O3B C8D . . 117.9(7) ?
C7B O3B C8B . . 112.8(9) ?
O3B C8B C9B . . 108.2(12) ?
O3B C8B H811 . . 110.0 ?
C9B C8B H811 . . 110.0 ?
O3B C8B H812 . . 110.0 ?
C9B C8B H812 . . 110.0 ?
H811 C8B H812 . . 108.4 ?
C8B C9B H911 . . 109.5 ?
C8B C9B H912 . . 109.5 ?
H911 C9B H912 . . 109.5 ?
C8B C9B H913 . . 109.5 ?
H911 C9B H913 . . 109.5 ?
H912 C9B H913 . . 109.5 ?
O3B C8D C9D . . 107.5(8) ?
O3B C8D H821 . . 110.2 ?
C9D C8D H821 . . 110.2 ?
O3B C8D H822 . . 110.2 ?
C9D C8D H822 . . 110.2 ?
H821 C8D H822 . . 108.5 ?
C8D C9D H921 . . 109.5 ?
C8D C9D H922 . . 109.5 ?
H921 C9D H922 . . 109.5 ?
C8D C9D H923 . . 109.5 ?
H921 C9D H923 . . 109.5 ?
H922 C9D H923 . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5A N1A C2A C7A . . . . 98.8(3) ?
C5A N1A C2A C3A . . . . -23.2(3) ?
N1A C2A C3A O1A . . . . -77.5(3) ?
C7A C2A C3A O1A . . . . 167.2(2) ?
N1A C2A C3A C4A . . . . 40.2(3) ?
C7A C2A C3A C4A . . . . -75.1(3) ?
N1A C2A C3A C6A . . . . 161.8(2) ?
C7A C2A C3A C6A . . . . 46.4(4) ?
O1A C3A C4A C5A . . . . 69.7(3) ?
C6A C3A C4A C5A . . . . -167.4(2) ?
C2A C3A C4A C5A . . . . -42.6(3) ?
C2A N1A C5A C4A . . . . -2.6(3) ?
C3A C4A C5A N1A . . . . 27.8(3) ?
O1A C3A C6A F2A . . . . 179.3(2) ?
C4A C3A C6A F2A . . . . 54.7(4) ?
C2A C3A C6A F2A . . . . -62.4(4) ?
O1A C3A C6A F1A . . . . 61.9(3) ?
C4A C3A C6A F1A . . . . -62.7(3) ?
C2A C3A C6A F1A . . . . -179.7(2) ?
O1A C3A C6A Cl1A . . . . -57.1(3) ?
C4A C3A C6A Cl1A . . . . 178.3(2) ?
C2A C3A C6A Cl1A . . . . 61.2(3) ?
N1A C2A C7A O2A . . . . -19.4(4) ?
C3A C2A C7A O2A . . . . 92.6(4) ?
N1A C2A C7A O3A . . . . 159.9(2) ?
C3A C2A C7A O3A . . . . -88.1(3) ?
O2A C7A O3A C8C . . . . -7.(3) ?
C2A C7A O3A C8C . . . . 174.(3) ?
O2A C7A O3A C8A . . . . -2.6(6) ?
C2A C7A O3A C8A . . . . 178.1(5) ?
C7A O3A C8A C9A . . . . 165.7(7) ?
C7A O3A C8C C9C . . . . 127.(5) ?
C5B N1B C2B C7B . . . . 94.4(3) ?
C5B N1B C2B C3B . . . . -26.6(3) ?
F1B C6B C3B O1B . . . . 179.3(3) ?
F2D C6B C3B O1B . . . . -46.(2) ?
F1D C6B C3B O1B . . . . -158.8(18) ?
F2B C6B C3B O1B . . . . -60.0(3) ?
Cl1D C6B C3B O1B . . . . 90.2(10) ?
Cl1B C6B C3B O1B . . . . 59.8(3) ?
F1B C6B C3B C4B . . . . 52.9(4) ?
F2D C6B C3B C4B . . . . -172.(2) ?
F1D C6B C3B C4B . . . . 74.8(18) ?
F2B C6B C3B C4B . . . . 173.6(3) ?
Cl1D C6B C3B C4B . . . . -36.1(10) ?
Cl1B C6B C3B C4B . . . . -66.5(3) ?
F1B C6B C3B C2B . . . . -64.7(4) ?
F2D C6B C3B C2B . . . . 70.(2) ?
F1D C6B C3B C2B . . . . -42.8(18) ?
F2B C6B C3B C2B . . . . 56.1(4) ?
Cl1D C6B C3B C2B . . . . -153.7(10) ?
Cl1B C6B C3B C2B . . . . 175.9(2) ?
N1B C2B C3B O1B . . . . -76.8(3) ?
C7B C2B C3B O1B . . . . 168.3(3) ?
N1B C2B C3B C4B . . . . 41.0(3) ?
C7B C2B C3B C4B . . . . -73.9(3) ?
N1B C2B C3B C6B . . . . 164.7(3) ?
C7B C2B C3B C6B . . . . 49.8(4) ?
O1B C3B C4B C5B . . . . 71.1(3) ?
C6B C3B C4B C5B . . . . -164.7(3) ?
C2B C3B C4B C5B . . . . -40.8(3) ?
C2B N1B C5B C4B . . . . 2.4(3) ?
C3B C4B C5B N1B . . . . 24.1(3) ?
N1B C2B C7B O2B . . . . -25.6(4) ?
C3B C2B C7B O2B . . . . 85.2(4) ?
N1B C2B C7B O3B . . . . 153.1(3) ?
C3B C2B C7B O3B . . . . -96.1(3) ?
O2B C7B O3B C8D . . . . 2.2(8) ?
C2B C7B O3B C8D . . . . -176.5(6) ?
O2B C7B O3B C8B . . . . -8.6(10) ?
C2B C7B O3B C8B . . . . 172.7(9) ?
C7B O3B C8B C9B . . . . -148.3(14) ?
C7B O3B C8D C9D . . . . -100.7(12) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1A H1A O4A . 0.862(18) 2.03(2) 2.824(3) 153.(3) ?
N1A H1B Cl2A 2_755 0.861(19) 2.29(2) 3.087(3) 154.(4) ?
O1A H1 O4B 3_545 0.863(19) 1.78(2) 2.635(4) 172.(4) ?
O4A H4A Cl2A 1_565 0.861(18) 2.28(2) 3.125(2) 166.(3) ?
N1B H1C Cl2B 4_645 0.874(19) 2.24(2) 3.109(3) 173.(4) ?
N1B H1D Cl2B . 0.87(2) 2.48(4) 3.152(3) 134.(4) ?
O1B H2 O5B 1_545 0.851(19) 1.82(2) 2.650(3) 165.(4) ?
O4B H4C Cl2B . 0.853(19) 2.50(3) 3.265(3) 150.(4) ?
O4B H4C O2B . 0.853(19) 2.55(4) 3.081(4) 122.(4) ?
O4B H4D Cl2B 1_565 0.86(2) 2.25(2) 3.109(3) 174.(5) ?
O5B H5A Cl2A . 0.865(19) 2.36(2) 3.210(3) 168.(4) ?
O5B H5B Cl2A 1_565 0.863(19) 2.40(2) 3.240(3) 166.(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_haf8713
_database_code_depnum_ccdc_archive 'CCDC 1855495'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 F3 N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         197.12

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4217(13)
_cell_length_b                   20.9410(19)
_cell_length_c                   6.3348(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.730(7)
_cell_angle_gamma                90
_cell_volume                     1510.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3472
_cell_measurement_theta_min      4.2224
_cell_measurement_theta_max      65.4818
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800

_exptl_absorpt_coefficient_mu    1.654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'KappaCCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            18311
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_theta_min         3.88
_diffrn_reflns_theta_max         66.71
_diffrn_reflns_theta_full        66.71
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7

_refine_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.
;

_reflns_number_total             2632
_reflns_number_gt                1810
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1364
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_number_reflns         2632
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+1.5174P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.278
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0026(4)

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

_computing_data_collection       'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL--2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1A 0.4444(3) 0.91783(13) 0.3896(5) 0.0355(7) Uani d . . . 1 . .
H H1 0.493(3) 0.9451(19) 0.345(6) 0.044(11) Uiso d . . . 1 . .
O O1A 0.3970(2) 0.97713(11) 0.6725(4) 0.0421(6) Uani d . . . 1 . .
O O2A 0.5183(2) 0.75926(10) 0.2110(3) 0.0353(6) Uani d . . . 1 . .
O O3A 0.6259(2) 0.83731(10) 0.3761(4) 0.0350(6) Uani d . . . 1 . .
H H3A 0.6813 0.8112 0.3686 0.052 Uiso calc U . R 1 . .
F F1A 0.17828(19) 0.89245(10) 0.2345(3) 0.0502(6) Uani d . . . 1 . .
F F2A 0.11907(19) 0.80936(10) 0.3912(4) 0.0572(6) Uani d . . . 1 . .
F F3A 0.2070(2) 0.79970(12) 0.1041(4) 0.0644(7) Uani d . . . 1 . .
C C1A 0.4222(3) 0.85619(15) 0.2897(5) 0.0336(8) Uani d . . . 1 . .
H H1A 0.3902 0.8633 0.1398 0.04 Uiso calc U . R 1 . .
C C2A 0.3238(3) 0.82755(15) 0.4145(5) 0.0354(8) Uani d . . . 1 . .
H H2A 0.3418 0.7819 0.4498 0.042 Uiso calc U . R 1 . .
C C3A 0.3268(3) 0.86721(16) 0.6181(5) 0.0385(8) Uani d . . . 1 . .
H H301 0.2462 0.8773 0.6549 0.046 Uiso calc U . R 1 . .
H H302 0.3688 0.8442 0.7381 0.046 Uiso calc U . R 1 . .
C C4A 0.3920(3) 0.92729(15) 0.5654(5) 0.0360(8) Uani d . . . 1 . .
C C5A 0.5287(3) 0.81233(15) 0.2896(5) 0.0321(8) Uani d . . . 1 . .
C C6A 0.2080(3) 0.83226(17) 0.2887(6) 0.0423(9) Uani d . . . 1 . .
N N1B 0.7240(3) 0.67590(12) 0.3184(4) 0.0329(7) Uani d . . . 1 . .
H H2 0.656(3) 0.6891(17) 0.285(5) 0.034(10) Uiso d . . . 1 . .
O O1B 0.8140(2) 0.77309(10) 0.3672(4) 0.0384(6) Uani d . . . 1 . .
O O2B 0.5749(2) 0.58941(11) 0.4807(4) 0.0386(6) Uani d . . . 1 . .
O O3B 0.7207(2) 0.51765(12) 0.5205(4) 0.0496(7) Uani d . . . 1 . .
H H3B 0.679 0.5015 0.6097 0.074 Uiso calc U . R 1 . .
F F1B 0.9329(2) 0.59578(11) 0.0175(4) 0.0580(7) Uani d . . . 1 . .
F F2B 1.0637(2) 0.56688(11) 0.2629(4) 0.0652(7) Uani d . . . 1 . .
F F3B 0.9103(2) 0.50868(10) 0.1871(4) 0.0704(8) Uani d . . . 1 . .
C C1B 0.7503(3) 0.60790(15) 0.3078(5) 0.0347(8) Uani d . . . 1 . .
H H1B 0.7347 0.5929 0.1582 0.042 Uiso calc U . R 1 . .
C C2B 0.8844(3) 0.60482(16) 0.3715(6) 0.0378(8) Uani d . . . 1 . .
H H2B 0.8983 0.5832 0.512 0.045 Uiso calc U . R 1 . .
C C3B 0.9259(3) 0.67444(17) 0.3918(6) 0.0441(9) Uani d . . . 1 . .
H H311 0.966 0.6824 0.5339 0.053 Uiso calc U . R 1 . .
H H312 0.9808 0.6845 0.2835 0.053 Uiso calc U . R 1 . .
C C4B 0.8170(3) 0.71383(16) 0.3585(5) 0.0338(8) Uani d . . . 1 . .
C C5B 0.6723(3) 0.57141(16) 0.4475(5) 0.0344(8) Uani d . . . 1 . .
C C6B 0.9477(4) 0.56914(16) 0.2101(7) 0.0473(10) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1A C4A . 1.322(4) ?
N1A C1A . 1.451(4) ?
N1A H1 . 0.86(4) ?
O1A C4A . 1.243(4) ?
O2A C5A . 1.220(4) ?
O3A C5A . 1.306(4) ?
O3A H3A . 0.84 ?
F1A C6A . 1.342(4) ?
F2A C6A . 1.339(4) ?
F3A C6A . 1.353(4) ?
C1A C5A . 1.525(5) ?
C1A C2A . 1.547(5) ?
C1A H1A . 1.0 ?
C2A C6A . 1.491(5) ?
C2A C3A . 1.532(5) ?
C2A H2A . 1.0 ?
C3A C4A . 1.513(5) ?
C3A H301 . 0.99 ?
C3A H302 . 0.99 ?
N1B C4B . 1.334(5) ?
N1B C1B . 1.458(4) ?
N1B H2 . 0.84(4) ?
O1B C4B . 1.243(4) ?
O2B C5B . 1.209(4) ?
O3B C5B . 1.322(4) ?
O3B H3B . 0.84 ?
F1B C6B . 1.340(5) ?
F2B C6B . 1.341(5) ?
F3B C6B . 1.340(4) ?
C1B C5B . 1.514(5) ?
C1B C2B . 1.552(5) ?
C1B H1B . 1.0 ?
C2B C6B . 1.500(5) ?
C2B C3B . 1.535(5) ?
C2B H2B . 1.0 ?
C3B C4B . 1.492(5) ?
C3B H311 . 0.99 ?
C3B H312 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4A N1A C1A . . 115.2(3) ?
C4A N1A H1 . . 122.(3) ?
C1A N1A H1 . . 123.(3) ?
C5A O3A H3A . . 109.5 ?
N1A C1A C5A . . 115.2(3) ?
N1A C1A C2A . . 103.3(3) ?
C5A C1A C2A . . 112.3(3) ?
N1A C1A H1A . . 108.6 ?
C5A C1A H1A . . 108.6 ?
C2A C1A H1A . . 108.6 ?
C6A C2A C3A . . 111.8(3) ?
C6A C2A C1A . . 110.5(3) ?
C3A C2A C1A . . 104.7(3) ?
C6A C2A H2A . . 109.9 ?
C3A C2A H2A . . 109.9 ?
C1A C2A H2A . . 109.9 ?
C4A C3A C2A . . 104.0(3) ?
C4A C3A H301 . . 111.0 ?
C2A C3A H301 . . 111.0 ?
C4A C3A H302 . . 111.0 ?
C2A C3A H302 . . 111.0 ?
H301 C3A H302 . . 109.0 ?
O1A C4A N1A . . 125.6(3) ?
O1A C4A C3A . . 125.4(3) ?
N1A C4A C3A . . 109.1(3) ?
O2A C5A O3A . . 126.0(3) ?
O2A C5A C1A . . 119.8(3) ?
O3A C5A C1A . . 114.2(3) ?
F2A C6A F1A . . 106.0(3) ?
F2A C6A F3A . . 106.7(3) ?
F1A C6A F3A . . 105.6(3) ?
F2A C6A C2A . . 113.1(3) ?
F1A C6A C2A . . 113.2(3) ?
F3A C6A C2A . . 111.8(3) ?
C4B N1B C1B . . 115.2(3) ?
C4B N1B H2 . . 124.(2) ?
C1B N1B H2 . . 120.(2) ?
C5B O3B H3B . . 109.5 ?
N1B C1B C5B . . 109.4(3) ?
N1B C1B C2B . . 103.4(3) ?
C5B C1B C2B . . 116.3(3) ?
N1B C1B H1B . . 109.2 ?
C5B C1B H1B . . 109.2 ?
C2B C1B H1B . . 109.2 ?
C6B C2B C3B . . 111.6(3) ?
C6B C2B C1B . . 111.4(3) ?
C3B C2B C1B . . 105.9(3) ?
C6B C2B H2B . . 109.3 ?
C3B C2B H2B . . 109.3 ?
C1B C2B H2B . . 109.3 ?
C4B C3B C2B . . 105.4(3) ?
C4B C3B H311 . . 110.7 ?
C2B C3B H311 . . 110.7 ?
C4B C3B H312 . . 110.7 ?
C2B C3B H312 . . 110.7 ?
H311 C3B H312 . . 108.8 ?
O1B C4B N1B . . 125.3(3) ?
O1B C4B C3B . . 124.9(3) ?
N1B C4B C3B . . 109.8(3) ?
O2B C5B O3B . . 124.7(3) ?
O2B C5B C1B . . 122.6(3) ?
O3B C5B C1B . . 112.6(3) ?
F1B C6B F3B . . 106.2(3) ?
F1B C6B F2B . . 106.9(3) ?
F3B C6B F2B . . 107.1(3) ?
F1B C6B C2B . . 112.4(3) ?
F3B C6B C2B . . 112.2(3) ?
F2B C6B C2B . . 111.7(3) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C4A N1A C1A C5A . . . . -113.5(3) ?
C4A N1A C1A C2A . . . . 9.4(4) ?
N1A C1A C2A C6A . . . . 103.3(3) ?
C5A C1A C2A C6A . . . . -132.0(3) ?
N1A C1A C2A C3A . . . . -17.3(3) ?
C5A C1A C2A C3A . . . . 107.4(3) ?
C6A C2A C3A C4A . . . . -100.8(3) ?
C1A C2A C3A C4A . . . . 18.9(4) ?
C1A N1A C4A O1A . . . . -178.1(3) ?
C1A N1A C4A C3A . . . . 3.0(4) ?
C2A C3A C4A O1A . . . . 167.0(3) ?
C2A C3A C4A N1A . . . . -14.1(4) ?
N1A C1A C5A O2A . . . . 179.3(3) ?
C2A C1A C5A O2A . . . . 61.4(4) ?
N1A C1A C5A O3A . . . . -1.4(4) ?
C2A C1A C5A O3A . . . . -119.3(3) ?
C3A C2A C6A F2A . . . . -62.5(4) ?
C1A C2A C6A F2A . . . . -178.7(3) ?
C3A C2A C6A F1A . . . . 58.0(4) ?
C1A C2A C6A F1A . . . . -58.2(4) ?
C3A C2A C6A F3A . . . . 177.1(3) ?
C1A C2A C6A F3A . . . . 60.9(4) ?
C4B N1B C1B C5B . . . . 129.8(3) ?
C4B N1B C1B C2B . . . . 5.2(4) ?
N1B C1B C2B C6B . . . . -127.1(3) ?
C5B C1B C2B C6B . . . . 113.0(3) ?
N1B C1B C2B C3B . . . . -5.7(3) ?
C5B C1B C2B C3B . . . . -125.6(3) ?
C6B C2B C3B C4B . . . . 125.8(3) ?
C1B C2B C3B C4B . . . . 4.5(4) ?
C1B N1B C4B O1B . . . . 177.5(3) ?
C1B N1B C4B C3B . . . . -2.5(4) ?
C2B C3B C4B O1B . . . . 178.5(3) ?
C2B C3B C4B N1B . . . . -1.5(4) ?
N1B C1B C5B O2B . . . . 30.0(5) ?
C2B C1B C5B O2B . . . . 146.6(3) ?
N1B C1B C5B O3B . . . . -152.2(3) ?
C2B C1B C5B O3B . . . . -35.6(4) ?
C3B C2B C6B F1B . . . . -58.9(4) ?
C1B C2B C6B F1B . . . . 59.2(4) ?
C3B C2B C6B F3B . . . . -178.5(3) ?
C1B C2B C6B F3B . . . . -60.5(4) ?
C3B C2B C6B F2B . . . . 61.3(4) ?
C1B C2B C6B F2B . . . . 179.3(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1A H1 O1A 3_676 0.86(4) 2.06(4) 2.897(4) 162.(4) ?
O3A H3A O1B . 0.84 1.71 2.538(3) 166.8 ?
C3A H301 F2B 4_476 0.99 2.53 3.496(4) 164.5 ?
N1B H2 O2A . 0.84(4) 2.17(4) 2.961(4) 157.(3) ?
O3B H3B O1A 2_646 0.84 1.76 2.597(3) 170.2 ?

####################################################################### 
# 
# 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_haf8797
_database_code_depnum_ccdc_archive 'CCDC 1855496'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H25 F3 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         386.41
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.4312(2)
_cell_length_b                   44.5944(10)
_cell_length_c                   9.6364(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.151(2)
_cell_angle_gamma                90
_cell_volume                     4046.74(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9123
_cell_measurement_theta_min      4.5956
_cell_measurement_theta_max      66.7499
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.214
_exptl_crystal_size_mid          0.203
_exptl_crystal_size_min          0.038
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1632

_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            37191
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_theta_min         3.96
_diffrn_reflns_theta_max         65.05
_diffrn_reflns_theta_full        65.05
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11

_refine_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.
;

_reflns_number_total             12106
_reflns_number_gt                10067
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1038
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.077
_refine_ls_number_reflns         12106
_refine_ls_number_parameters     1054
_refine_ls_number_restraints     130
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0211P)²+3.0274P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.234
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 3590 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(8)

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

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1A 0.1506(5) 0.32183(8) 0.4073(4) 0.0368(11) Uani d . . . 1.0 . .
O O2A 0.3181(4) 0.31412(7) 0.5836(4) 0.0269(9) Uani d . . . 1.0 . .
O O3A 0.4008(4) 0.36135(8) 0.2205(4) 0.0309(10) Uani d . . . 1.0 . .
N N1A 0.2874(5) 0.35997(9) 0.4929(5) 0.0235(11) Uani d . . . 1.0 . .
N N2A 0.1695(5) 0.36393(9) 0.1441(4) 0.0201(10) Uani d . . . 1.0 . .
H H1 0.076(7) 0.3661(13) 0.169(6) 0.041(19) Uiso d . . . 1.0 . .
F F1A 0.1041(4) 0.43778(8) 0.4466(4) 0.0567(11) Uani d . . . 1.0 . .
F F2A 0.2950(4) 0.46197(7) 0.4047(4) 0.0530(11) Uani d . . . 1.0 . .
F F3A 0.1842(4) 0.43642(7) 0.2419(4) 0.0499(10) Uani d . . . 1.0 . .
C C2A 0.2345(6) 0.37991(11) 0.3799(5) 0.0191(12) Uani d . . . 1.0 . .
H H2A 0.1294 0.3826 0.3817 0.023 Uiso calc U . R 1.0 . .
C C3A 0.3129(6) 0.40951(11) 0.4165(5) 0.0240(13) Uani d . . . 1.0 . .
H H3A 0.4002 0.4103 0.3621 0.029 Uiso calc U . R 1.0 . .
C C4A 0.3597(7) 0.40721(11) 0.5698(6) 0.0272(14) Uani d . . . 1.0 . .
H H401 0.2829 0.4136 0.6294 0.033 Uiso calc U . R 1.0 . .
H H402 0.4452 0.4196 0.592 0.033 Uiso calc U . R 1.0 . .
C C5A 0.3921(6) 0.37390(11) 0.5877(6) 0.0268(14) Uani d . . . 1.0 . .
H H501 0.4898 0.3692 0.5618 0.032 Uiso calc U . R 1.0 . .
H H502 0.3805 0.3674 0.6846 0.032 Uiso calc U . R 1.0 . .
C C6A 0.2242(7) 0.43621(13) 0.3782(7) 0.0370(16) Uani d . . . 1.0 . .
C C7A 0.2440(7) 0.33088(12) 0.4881(6) 0.0273(14) Uani d . . . 1.0 . .
C C8A 0.2885(7) 0.28159(11) 0.5911(6) 0.0310(15) Uani d . . . 1.0 . .
C C9A 0.3114(8) 0.26663(13) 0.4522(7) 0.0469(19) Uani d . . . 1.0 . .
H H901 0.2353 0.2726 0.3845 0.07 Uiso calc U . R 1.0 . .
H H902 0.3105 0.2448 0.4638 0.07 Uiso calc U . R 1.0 . .
H H903 0.4032 0.2729 0.419 0.07 Uiso calc U . R 1.0 . .
C C10A 0.1385(7) 0.27683(14) 0.6395(7) 0.0391(16) Uani d . . . 1.0 . .
H H10A 0.125 0.2891 0.722 0.059 Uiso calc U . R 1.0 . .
H H10B 0.1254 0.2556 0.6625 0.059 Uiso calc U . R 1.0 . .
H H10C 0.0689 0.2827 0.5651 0.059 Uiso calc U . R 1.0 . .
C C11A 0.4010(7) 0.27151(13) 0.7005(7) 0.0406(17) Uani d . . . 1.0 . .
H H11A 0.4954 0.2767 0.6701 0.061 Uiso calc U . R 1.0 . .
H H11B 0.3945 0.2498 0.7132 0.061 Uiso calc U . R 1.0 . .
H H11C 0.3855 0.2816 0.7887 0.061 Uiso calc U . R 1.0 . .
C C12A 0.2751(6) 0.36751(11) 0.2402(6) 0.0230(13) Uani d . . . 1.0 . .
C C13A 0.1977(6) 0.35014(11) 0.0095(5) 0.0236(13) Uani d . . . 1.0 . .
H H13A 0.2871 0.359 -0.0235 0.028 Uiso calc U . R 1.0 . .
C C14A 0.2214(7) 0.31636(12) 0.0298(7) 0.0395(17) Uani d . . . 1.0 . .
H H14A 0.3036 0.3131 0.0947 0.059 Uiso calc U . R 1.0 . .
H H14B 0.2389 0.3071 -0.0598 0.059 Uiso calc U . R 1.0 . .
H H14C 0.1369 0.3074 0.0675 0.059 Uiso calc U . R 1.0 . .
C C15A 0.0774(6) 0.35780(12) -0.0957(6) 0.0263(13) Uani d . . . 1.0 . .
C C16A 0.0925(7) 0.38188(14) -0.1820(6) 0.0384(16) Uani d . . . 1.0 . .
H H16A 0.1759 0.3938 -0.1716 0.046 Uiso calc U . R 1.0 . .
C C17A -0.0111(8) 0.38931(15) -0.2844(7) 0.0451(18) Uani d . . . 1.0 . .
H H17A 0.0032 0.4057 -0.3453 0.054 Uiso calc U . R 1.0 . .
C C18A -0.1354(8) 0.37272(15) -0.2972(7) 0.0452(18) Uani d . . . 1.0 . .
H H18A -0.2073 0.3777 -0.3663 0.054 Uiso calc U . R 1.0 . .
C C19A -0.1534(7) 0.34893(14) -0.2085(7) 0.0424(17) Uani d . . . 1.0 . .
H H19A -0.2385 0.3375 -0.2161 0.051 Uiso calc U . R 1.0 . .
C C20A -0.0483(7) 0.34167(13) -0.1086(6) 0.0342(15) Uani d . . . 1.0 . .
H H20A -0.0624 0.3253 -0.0477 0.041 Uiso calc U . R 1.0 . .
O O1B 0.6621(4) 0.42878(8) 0.4442(4) 0.0309(10) Uani d . . . 1.0 . .
O O3B 0.9050(4) 0.38095(8) 0.2489(4) 0.0299(9) Uani d . . . 1.0 . .
N N1B 0.7463(5) 0.43572(10) 0.2331(5) 0.0273(11) Uani d . . . 1.0 . .
N N2B 0.6965(6) 0.35837(10) 0.2881(5) 0.0255(11) Uani d . . . 1.0 . .
H H2 0.606(7) 0.3588(13) 0.281(6) 0.036(19) Uiso d . . . 1.0 . .
F F1B 0.5427(5) 0.44692(9) -0.0139(5) 0.0641(13) Uani d . . . 1.0 . .
F F2B 0.6073(5) 0.42254(13) -0.1921(4) 0.0860(17) Uani d . . . 1.0 . .
F F3B 0.4764(5) 0.40184(10) -0.0495(4) 0.0690(14) Uani d . . . 1.0 . .
C C2B 0.6903(6) 0.40727(11) 0.1804(5) 0.0221(12) Uani d . . . 1.0 . .
H H2B 0.5869 0.4053 0.1964 0.026 Uiso calc U . R 1.0 . .
C C3B 0.7153(7) 0.40901(15) 0.0248(6) 0.0364(16) Uani d . . . 1.0 . .
H H3B 0.7429 0.3888 -0.0097 0.044 Uiso calc U . R 1.0 . .
C C4B 0.8410(8) 0.43076(18) 0.0166(7) 0.058(2) Uani d . . . 1.0 . .
H H411 0.9323 0.4198 0.0278 0.07 Uiso calc U . R 1.0 . .
H H412 0.8369 0.4413 -0.074 0.07 Uiso calc U . R 1.0 . .
C C5B 0.8270(8) 0.45291(16) 0.1345(7) 0.052(2) Uani d . . . 1.0 . .
H H511 0.9213 0.4588 0.1761 0.063 Uiso calc U . R 1.0 . .
H H512 0.7748 0.4711 0.1025 0.063 Uiso calc U . R 1.0 . .
C C6B 0.5863(8) 0.41982(17) -0.0564(7) 0.0493(19) Uani d . . . 1.0 . .
C C7B 0.7232(7) 0.44416(12) 0.3647(7) 0.0321(15) Uani d . . D 1.0 . .
O O2B 0.7645(17) 0.4726(2) 0.3998(14) 0.027(3) Uani d U P D 0.58(3) A 1
C C8B 0.7464(15) 0.4853(3) 0.5383(14) 0.025(3) Uani d U P D 0.58(3) A 1
C C9B 0.828(2) 0.4679(5) 0.650(2) 0.027(5) Uani d U P D 0.58(3) A 1
H H911 0.7776 0.4493 0.6685 0.04 Uiso calc U P R 0.58(3) A 1
H H912 0.8379 0.48 0.7348 0.04 Uiso calc U P R 0.58(3) A 1
H H913 0.9228 0.4631 0.6184 0.04 Uiso calc U P R 0.58(3) A 1
C C10B 0.5905(14) 0.4870(3) 0.564(2) 0.044(4) Uani d U P D 0.58(3) A 1
H H10I 0.5381 0.4939 0.4789 0.066 Uiso calc U P R 0.58(3) A 1
H H10J 0.5757 0.5011 0.6394 0.066 Uiso calc U P R 0.58(3) A 1
H H10K 0.5563 0.4671 0.5889 0.066 Uiso calc U P R 0.58(3) A 1
C C11B 0.807(2) 0.5166(2) 0.5203(17) 0.039(4) Uani d U P D 0.58(3) A 1
H H11D 0.908 0.5151 0.5024 0.058 Uiso calc U P R 0.58(3) A 1
H H11E 0.7957 0.5283 0.6052 0.058 Uiso calc U P R 0.58(3) A 1
H H11F 0.7562 0.5265 0.4417 0.058 Uiso calc U P R 0.58(3) A 1
O O2E 0.8076(19) 0.4698(4) 0.3750(19) 0.024(4) Uani d U P D 0.42(3) A 2
C C8E 0.788(2) 0.4887(4) 0.500(2) 0.030(5) Uani d U P D 0.42(3) A 2
C C9E 0.633(2) 0.4975(6) 0.501(3) 0.059(7) Uani d U P D 0.42(3) A 2
H H921 0.6031 0.5067 0.4117 0.089 Uiso calc U P R 0.42(3) A 2
H H922 0.6204 0.5119 0.5762 0.089 Uiso calc U P R 0.42(3) A 2
H H923 0.5755 0.4796 0.5157 0.089 Uiso calc U P R 0.42(3) A 2
C C10E 0.884(3) 0.5150(3) 0.476(2) 0.045(6) Uani d U P D 0.42(3) A 2
H H10X 0.9815 0.5079 0.4699 0.068 Uiso calc U P R 0.42(3) A 2
H H10Y 0.8793 0.529 0.5541 0.068 Uiso calc U P R 0.42(3) A 2
H H10Z 0.8526 0.5251 0.3896 0.068 Uiso calc U P R 0.42(3) A 2
C C11E 0.847(4) 0.4713(7) 0.623(3) 0.037(8) Uani d U P D 0.42(3) A 2
H H11G 0.8134 0.4505 0.6162 0.056 Uiso calc U P R 0.42(3) A 2
H H11H 0.815 0.4804 0.7081 0.056 Uiso calc U P R 0.42(3) A 2
H H11I 0.9509 0.4716 0.6245 0.056 Uiso calc U P R 0.42(3) A 2
C C12B 0.7749(6) 0.38086(11) 0.2453(5) 0.0221(13) Uani d . . . 1.0 . .
C C13B 0.7593(6) 0.32994(11) 0.3371(6) 0.0250(13) Uani d . . . 1.0 . .
H H13B 0.8561 0.3341 0.3804 0.03 Uiso calc U . R 1.0 . .
C C14B 0.6687(7) 0.31667(12) 0.4470(6) 0.0365(16) Uani d . . . 1.0 . .
H H14D 0.667 0.3304 0.5262 0.055 Uiso calc U . R 1.0 . .
H H14E 0.7088 0.2974 0.4782 0.055 Uiso calc U . R 1.0 . .
H H14F 0.5717 0.3136 0.4077 0.055 Uiso calc U . R 1.0 . .
C C15B 0.7734(6) 0.30783(11) 0.2194(6) 0.0268(14) Uani d . . . 1.0 . .
C C16B 0.6715(7) 0.30589(14) 0.1111(6) 0.0392(16) Uani d . . . 1.0 . .
H H16B 0.5913 0.3188 0.1085 0.047 Uiso calc U . R 1.0 . .
C C17B 0.6871(8) 0.28460(16) 0.0040(7) 0.050(2) Uani d . . . 1.0 . .
H H17B 0.6184 0.2835 -0.0718 0.06 Uiso calc U . R 1.0 . .
C C18B 0.8003(9) 0.26582(14) 0.0099(7) 0.051(2) Uani d . . . 1.0 . .
H H18B 0.8098 0.2515 -0.062 0.061 Uiso calc U . R 1.0 . .
C C19B 0.9006(8) 0.26715(13) 0.1170(7) 0.0443(19) Uani d . . . 1.0 . .
H H19B 0.9784 0.2536 0.1202 0.053 Uiso calc U . R 1.0 . .
C C20B 0.8889(7) 0.28841(11) 0.2219(6) 0.0295(14) Uani d . . . 1.0 . .
H H20B 0.9601 0.2896 0.2953 0.035 Uiso calc U . R 1.0 . .
O O1C 0.0434(4) 0.67069(8) 0.3217(4) 0.0339(10) Uani d . . . 1.0 . .
O O2C 0.2308(4) 0.67503(7) 0.4807(4) 0.0255(9) Uani d . . . 1.0 . .
O O3C 0.4728(4) 0.63720(8) 0.3048(4) 0.0286(9) Uani d . . . 1.0 . .
N N1C 0.1848(5) 0.63100(9) 0.3798(4) 0.0234(11) Uani d . . . 1.0 . .
N N2C 0.5412(5) 0.63503(9) 0.5331(5) 0.0193(10) Uani d . . . 1.0 . .
H H3 0.523(6) 0.6294(11) 0.624(6) 0.025(15) Uiso d . . . 1.0 . .
F F1C 0.3314(4) 0.53360(7) 0.4510(4) 0.0490(11) Uani d . . . 1.0 . .
F F2C 0.4865(4) 0.56445(7) 0.5419(4) 0.0435(9) Uani d . . . 1.0 . .
F F3C 0.2784(4) 0.56158(7) 0.6215(3) 0.0401(9) Uani d . . . 1.0 . .
C C2C 0.3053(6) 0.61697(10) 0.4598(5) 0.0188(12) Uani d . . . 1.0 . .
H H2C 0.2913 0.6174 0.5619 0.023 Uiso calc U . R 1.0 . .
C C3C 0.2966(6) 0.58427(11) 0.4015(6) 0.0246(13) Uani d . . . 1.0 . .
H H3C 0.3581 0.5831 0.3204 0.03 Uiso calc U . R 1.0 . .
C C4C 0.1434(6) 0.58023(11) 0.3474(6) 0.0254(13) Uani d . . . 1.0 . .
H H431 0.1351 0.5642 0.2764 0.03 Uiso calc U . R 1.0 . .
H H432 0.0814 0.5753 0.4239 0.03 Uiso calc U . R 1.0 . .
C C5C 0.1060(7) 0.61045(11) 0.2849(6) 0.0294(14) Uani d . . . 1.0 . .
H H531 0.138 0.6121 0.1891 0.035 Uiso calc U . R 1.0 . .
H H532 0.0026 0.6142 0.284 0.035 Uiso calc U . R 1.0 . .
C C6C 0.3473(7) 0.56100(12) 0.5050(7) 0.0328(15) Uani d . . . 1.0 . .
C C7C 0.1435(6) 0.65975(12) 0.3888(6) 0.0253(13) Uani d . . . 1.0 . .
C C8C 0.2007(6) 0.70698(11) 0.5095(6) 0.0251(13) Uani d . . . 1.0 . .
C C9C 0.3170(7) 0.71465(13) 0.6204(7) 0.0425(18) Uani d . . . 1.0 . .
H H931 0.3064 0.702 0.7024 0.064 Uiso calc U . R 1.0 . .
H H932 0.3091 0.7358 0.6466 0.064 Uiso calc U . R 1.0 . .
H H933 0.4103 0.7111 0.5834 0.064 Uiso calc U . R 1.0 . .
C C10C 0.2186(8) 0.72565(13) 0.3795(7) 0.0421(17) Uani d . . . 1.0 . .
H H10P 0.3142 0.7226 0.347 0.063 Uiso calc U . R 1.0 . .
H H10R 0.2053 0.7469 0.4011 0.063 Uiso calc U . R 1.0 . .
H H10S 0.1479 0.7195 0.3068 0.063 Uiso calc U . R 1.0 . .
C C11C 0.0560(7) 0.71032(15) 0.5689(8) 0.051(2) Uani d . . . 1.0 . .
H H11X -0.018 0.7051 0.4976 0.076 Uiso calc U . R 1.0 . .
H H11Y 0.043 0.7311 0.5985 0.076 Uiso calc U . R 1.0 . .
H H11Z 0.0496 0.6969 0.6489 0.076 Uiso calc U . R 1.0 . .
C C12C 0.4472(6) 0.63109(10) 0.4259(5) 0.0198(12) Uani d . . . 1.0 . .
C C13C 0.6824(6) 0.64720(11) 0.5098(6) 0.0229(13) Uani d . . . 1.0 . .
H H13C 0.713 0.6385 0.4206 0.028 Uiso calc U . R 1.0 . .
C C14C 0.6752(7) 0.68110(12) 0.4912(7) 0.0360(16) Uani d . . . 1.0 . .
H H14G 0.6058 0.686 0.4151 0.054 Uiso calc U . R 1.0 . .
H H14H 0.7689 0.6887 0.4692 0.054 Uiso calc U . R 1.0 . .
H H14I 0.6463 0.6904 0.5773 0.054 Uiso calc U . R 1.0 . .
C C15C 0.7896(6) 0.63729(11) 0.6234(5) 0.0210(12) Uani d . . . 1.0 . .
C C16C 0.8786(7) 0.61344(13) 0.5998(6) 0.0327(15) Uani d . . . 1.0 . .
H H16C 0.869 0.6031 0.5135 0.039 Uiso calc U . R 1.0 . .
C C17C 0.9818(7) 0.60418(15) 0.6990(6) 0.0420(17) Uani d . . . 1.0 . .
H H17C 1.0416 0.5877 0.6802 0.05 Uiso calc U . R 1.0 . .
C C18C 0.9976(7) 0.61891(15) 0.8245(6) 0.0381(16) Uani d . . . 1.0 . .
H H18C 1.069 0.6129 0.8923 0.046 Uiso calc U . R 1.0 . .
C C19C 0.9077(7) 0.64258(13) 0.8504(6) 0.0338(15) Uani d . . . 1.0 . .
H H19C 0.9167 0.6528 0.937 0.041 Uiso calc U . R 1.0 . .
C C20C 0.8053(7) 0.65149(12) 0.7514(6) 0.0310(15) Uani d . . . 1.0 . .
H H20C 0.7442 0.6677 0.7712 0.037 Uiso calc U . R 1.0 . .
O O1D 0.2528(4) 0.56435(8) 1.0350(4) 0.0300(9) Uani d . . . 1.0 . .
O O3D 0.4649(4) 0.61726(8) 0.8041(4) 0.0300(10) Uani d . . . 1.0 . .
N N1D 0.4660(5) 0.56066(9) 0.9434(4) 0.0239(11) Uani d . . . 1.0 . .
N N2D 0.4459(5) 0.63930(9) 1.0150(4) 0.0241(11) Uani d . . . 1.0 . .
H H4 0.458(5) 0.6363(9) 1.118(5) 0.011(12) Uiso d . . . 1.0 . .
F F1D 0.6880(5) 0.54393(7) 1.1641(4) 0.0518(11) Uani d . . . 1.0 . .
F F2D 0.8848(5) 0.56633(9) 1.1293(5) 0.0652(13) Uani d . . . 1.0 . .
F F3D 0.7286(5) 0.58803(8) 1.2482(4) 0.0607(12) Uani d . . . 1.0 . .
C C2D 0.5185(6) 0.58795(11) 1.0110(5) 0.0195(12) Uani d . . . 1.0 . .
H H2D 0.4898 0.5888 1.1092 0.023 Uiso calc U . R 1.0 . .
C C3D 0.6819(7) 0.58461(13) 1.0061(6) 0.0329(15) Uani d . . . 1.0 . .
H H3D 0.7252 0.6048 0.9932 0.039 Uiso calc U . R 1.0 . .
C C4D 0.7005(7) 0.56571(16) 0.8766(6) 0.0425(17) Uani d . . . 1.0 . .
H H441 0.7915 0.5546 0.884 0.051 Uiso calc U . R 1.0 . .
H H442 0.6982 0.5784 0.7923 0.051 Uiso calc U . R 1.0 . .
C C5D 0.5739(7) 0.54402(15) 0.8722(6) 0.0409(17) Uani d . . . 1.0 . .
H H541 0.5411 0.5394 0.7752 0.049 Uiso calc U . R 1.0 . .
H H542 0.5987 0.5251 0.9214 0.049 Uiso calc U . R 1.0 . .
C C6D 0.7449(8) 0.57076(14) 1.1367(7) 0.0418(17) Uani d . . . 1.0 . .
C C7D 0.3369(7) 0.55055(11) 0.9682(6) 0.0253(14) Uani d . . . 1.0 . .
O O2D 0.3157(5) 0.52369(8) 0.9066(5) 0.0404(11) Uani d . . . 1.0 . .
C C8D 0.1857(8) 0.50643(12) 0.9302(8) 0.055(2) Uani d . . . 1.0 . .
C C9D 0.0578(7) 0.52316(14) 0.8694(9) 0.057(2) Uani d . . . 1.0 . .
H H941 -0.0278 0.5111 0.8803 0.086 Uiso calc U . R 1.0 . .
H H942 0.0693 0.5269 0.7704 0.086 Uiso calc U . R 1.0 . .
H H943 0.049 0.5423 0.9179 0.086 Uiso calc U . R 1.0 . .
C C10D 0.1820(12) 0.4997(2) 1.0840(10) 0.114(4) Uani d U . . 1.0 . .
H H10L 0.1053 0.4855 1.0995 0.171 Uiso calc U . R 1.0 . .
H H10M 0.1654 0.5184 1.1346 0.171 Uiso calc U . R 1.0 . .
H H10N 0.2729 0.491 1.1174 0.171 Uiso calc U . R 1.0 . .
C C11D 0.2085(9) 0.47831(14) 0.8461(11) 0.098(4) Uani d U . . 1.0 . .
H H11J 0.1253 0.4652 0.8502 0.146 Uiso calc U . R 1.0 . .
H H11K 0.2929 0.4677 0.8845 0.146 Uiso calc U . R 1.0 . .
H H11L 0.2221 0.4838 0.7493 0.146 Uiso calc U . R 1.0 . .
C C12D 0.4713(6) 0.61620(12) 0.9317(5) 0.0236(13) Uani d . . . 1.0 . .
C C13D 0.4228(7) 0.66992(11) 0.9649(6) 0.0286(14) Uani d . . . 1.0 . .
H H13D 0.4031 0.669 0.862 0.034 Uiso calc U . R 1.0 . .
C C14D 0.2932(7) 0.68261(14) 1.0285(7) 0.0436(17) Uani d . . . 1.0 . .
H H14J 0.2122 0.6692 1.0085 0.065 Uiso calc U . R 1.0 . .
H H14K 0.2721 0.7025 0.989 0.065 Uiso calc U . R 1.0 . .
H H14L 0.3112 0.6844 1.1293 0.065 Uiso calc U . R 1.0 . .
C C15D 0.5545(6) 0.68961(11) 0.9937(5) 0.0248(14) Uani d . . . 1.0 . .
C C16D 0.6627(7) 0.68156(12) 1.0892(6) 0.0299(14) Uani d . . . 1.0 . .
H H16D 0.6564 0.6633 1.1389 0.036 Uiso calc U . R 1.0 . .
C C17D 0.7804(7) 0.69998(13) 1.1133(6) 0.0348(15) Uani d . . . 1.0 . .
H H17D 0.8539 0.6942 1.1793 0.042 Uiso calc U . R 1.0 . .
C C18D 0.7910(7) 0.72668(13) 1.0415(6) 0.0350(16) Uani d . . . 1.0 . .
H H18D 0.8719 0.7392 1.0568 0.042 Uiso calc U . R 1.0 . .
C C19D 0.6821(8) 0.73497(13) 0.9470(6) 0.0396(17) Uani d . . . 1.0 . .
H H19D 0.6881 0.7533 0.8977 0.048 Uiso calc U . R 1.0 . .
C C20D 0.5648(7) 0.71670(12) 0.9240(6) 0.0325(15) Uani d . . . 1.0 . .
H H20D 0.4903 0.7228 0.8598 0.039 Uiso calc U . R 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1A C7A . 1.212(7) ?
O2A C7A . 1.351(6) ?
O2A C8A . 1.480(6) ?
O3A C12A . 1.242(6) ?
N1A C7A . 1.361(7) ?
N1A C5A . 1.448(6) ?
N1A C2A . 1.471(6) ?
N2A C12A . 1.331(7) ?
N2A C13A . 1.473(6) ?
N2A H1 . 0.93(7) ?
F1A C6A . 1.343(8) ?
F2A C6A . 1.346(7) ?
F3A C6A . 1.347(7) ?
C2A C12A . 1.524(7) ?
C2A C3A . 1.544(7) ?
C2A H2A . 1.0 ?
C3A C6A . 1.490(8) ?
C3A C4A . 1.522(7) ?
C3A H3A . 1.0 ?
C4A C5A . 1.525(7) ?
C4A H401 . 0.99 ?
C4A H402 . 0.99 ?
C5A H501 . 0.99 ?
C5A H502 . 0.99 ?
C8A C9A . 1.521(8) ?
C8A C11A . 1.522(8) ?
C8A C10A . 1.529(9) ?
C9A H901 . 0.98 ?
C9A H902 . 0.98 ?
C9A H903 . 0.98 ?
C10A H10A . 0.98 ?
C10A H10B . 0.98 ?
C10A H10C . 0.98 ?
C11A H11A . 0.98 ?
C11A H11B . 0.98 ?
C11A H11C . 0.98 ?
C13A C15A . 1.518(8) ?
C13A C14A . 1.534(7) ?
C13A H13A . 1.0 ?
C14A H14A . 0.98 ?
C14A H14B . 0.98 ?
C14A H14C . 0.98 ?
C15A C16A . 1.370(8) ?
C15A C20A . 1.386(8) ?
C16A C17A . 1.390(8) ?
C16A H16A . 0.95 ?
C17A C18A . 1.386(9) ?
C17A H17A . 0.95 ?
C18A C19A . 1.379(9) ?
C18A H18A . 0.95 ?
C19A C20A . 1.382(8) ?
C19A H19A . 0.95 ?
C20A H20A . 0.95 ?
O1B C7B . 1.200(7) ?
O3B C12B . 1.226(6) ?
N1B C7B . 1.352(7) ?
N1B C2B . 1.455(6) ?
N1B C5B . 1.466(7) ?
N2B C12B . 1.325(7) ?
N2B C13B . 1.466(6) ?
N2B H2 . 0.86(6) ?
F1B C6B . 1.348(8) ?
F2B C6B . 1.339(8) ?
F3B C6B . 1.315(8) ?
C2B C3B . 1.532(8) ?
C2B C12B . 1.536(7) ?
C2B H2B . 1.0 ?
C3B C6B . 1.490(9) ?
C3B C4B . 1.537(9) ?
C3B H3B . 1.0 ?
C4B C5B . 1.516(10) ?
C4B H411 . 0.99 ?
C4B H412 . 0.99 ?
C5B H511 . 0.99 ?
C5B H512 . 0.99 ?
C7B O2B . 1.364(11) ?
C7B O2E . 1.393(15) ?
O2B C8B . 1.469(13) ?
C8B C9B . 1.504(13) ?
C8B C10B . 1.505(14) ?
C8B C11B . 1.519(13) ?
C9B H911 . 0.98 ?
C9B H912 . 0.98 ?
C9B H913 . 0.98 ?
C10B H10I . 0.98 ?
C10B H10J . 0.98 ?
C10B H10K . 0.98 ?
C11B H11D . 0.98 ?
C11B H11E . 0.98 ?
C11B H11F . 0.98 ?
O2E C8E . 1.486(17) ?
C8E C11E . 1.498(17) ?
C8E C10E . 1.503(16) ?
C8E C9E . 1.514(16) ?
C9E H921 . 0.98 ?
C9E H922 . 0.98 ?
C9E H923 . 0.98 ?
C10E H10X . 0.98 ?
C10E H10Y . 0.98 ?
C10E H10Z . 0.98 ?
C11E H11G . 0.98 ?
C11E H11H . 0.98 ?
C11E H11I . 0.98 ?
C13B C15B . 1.515(7) ?
C13B C14B . 1.517(8) ?
C13B H13B . 1.0 ?
C14B H14D . 0.98 ?
C14B H14E . 0.98 ?
C14B H14F . 0.98 ?
C15B C16B . 1.382(8) ?
C15B C20B . 1.391(8) ?
C16B C17B . 1.416(9) ?
C16B H16B . 0.95 ?
C17B C18B . 1.355(10) ?
C17B H17B . 0.95 ?
C18B C19B . 1.363(10) ?
C18B H18B . 0.95 ?
C19B C20B . 1.395(8) ?
C19B H19B . 0.95 ?
C20B H20B . 0.95 ?
O1C C7C . 1.217(6) ?
O2C C7C . 1.359(6) ?
O2C C8C . 1.482(6) ?
O3C C12C . 1.236(6) ?
N1C C7C . 1.344(7) ?
N1C C5C . 1.468(6) ?
N1C C2C . 1.476(6) ?
N2C C12C . 1.335(6) ?
N2C C13C . 1.467(7) ?
N2C H3 . 0.93(5) ?
F1C C6C . 1.334(6) ?
F2C C6C . 1.349(7) ?
F3C C6C . 1.328(7) ?
C2C C12C . 1.531(7) ?
C2C C3C . 1.564(7) ?
C2C H2C . 1.0 ?
C3C C6C . 1.499(7) ?
C3C C4C . 1.519(8) ?
C3C H3C . 1.0 ?
C4C C5C . 1.510(7) ?
C4C H431 . 0.99 ?
C4C H432 . 0.99 ?
C5C H531 . 0.99 ?
C5C H532 . 0.99 ?
C8C C11C . 1.515(9) ?
C8C C10C . 1.521(8) ?
C8C C9C . 1.528(8) ?
C9C H931 . 0.98 ?
C9C H932 . 0.98 ?
C9C H933 . 0.98 ?
C10C H10P . 0.98 ?
C10C H10R . 0.98 ?
C10C H10S . 0.98 ?
C11C H11X . 0.98 ?
C11C H11Y . 0.98 ?
C11C H11Z . 0.98 ?
C13C C15C . 1.514(7) ?
C13C C14C . 1.523(7) ?
C13C H13C . 1.0 ?
C14C H14G . 0.98 ?
C14C H14H . 0.98 ?
C14C H14I . 0.98 ?
C15C C16C . 1.381(8) ?
C15C C20C . 1.387(7) ?
C16C C17C . 1.389(8) ?
C16C H16C . 0.95 ?
C17C C18C . 1.377(8) ?
C17C H17C . 0.95 ?
C18C C19C . 1.385(9) ?
C18C H18C . 0.95 ?
C19C C20C . 1.379(8) ?
C19C H19C . 0.95 ?
C20C H20C . 0.95 ?
O1D C7D . 1.216(7) ?
O3D C12D . 1.229(6) ?
N1D C7D . 1.333(7) ?
N1D C2D . 1.454(6) ?
N1D C5D . 1.461(7) ?
N2D C12D . 1.335(7) ?
N2D C13D . 1.460(6) ?
N2D H4 . 1.00(5) ?
F1D C6D . 1.343(7) ?
F2D C6D . 1.340(8) ?
F3D C6D . 1.337(7) ?
C2D C12D . 1.527(7) ?
C2D C3D . 1.551(8) ?
C2D H2D . 1.0 ?
C3D C6D . 1.496(8) ?
C3D C4D . 1.524(9) ?
C3D H3D . 1.0 ?
C4D C5D . 1.535(9) ?
C4D H441 . 0.99 ?
C4D H442 . 0.99 ?
C5D H541 . 0.99 ?
C5D H542 . 0.99 ?
C7D O2D . 1.347(6) ?
O2D C8D . 1.476(8) ?
C8D C9D . 1.509(9) ?
C8D C10D . 1.514(11) ?
C8D C11D . 1.515(10) ?
C9D H941 . 0.98 ?
C9D H942 . 0.98 ?
C9D H943 . 0.98 ?
C10D H10L . 0.98 ?
C10D H10M . 0.98 ?
C10D H10N . 0.98 ?
C11D H11J . 0.98 ?
C11D H11K . 0.98 ?
C11D H11L . 0.98 ?
C13D C14D . 1.507(8) ?
C13D C15D . 1.533(8) ?
C13D H13D . 1.0 ?
C14D H14J . 0.98 ?
C14D H14K . 0.98 ?
C14D H14L . 0.98 ?
C15D C16D . 1.384(8) ?
C15D C20D . 1.388(7) ?
C16D C17D . 1.391(8) ?
C16D H16D . 0.95 ?
C17D C18D . 1.384(8) ?
C17D H17D . 0.95 ?
C18D C19D . 1.384(9) ?
C18D H18D . 0.95 ?
C19D C20D . 1.382(8) ?
C19D H19D . 0.95 ?
C20D H20D . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7A O2A C8A . . 118.9(4) ?
C7A N1A C5A . . 128.6(4) ?
C7A N1A C2A . . 117.5(4) ?
C5A N1A C2A . . 113.5(4) ?
C12A N2A C13A . . 119.9(5) ?
C12A N2A H1 . . 119.(4) ?
C13A N2A H1 . . 119.(4) ?
N1A C2A C12A . . 110.1(4) ?
N1A C2A C3A . . 102.1(4) ?
C12A C2A C3A . . 111.8(4) ?
N1A C2A H2A . . 110.9 ?
C12A C2A H2A . . 110.9 ?
C3A C2A H2A . . 110.9 ?
C6A C3A C4A . . 115.0(5) ?
C6A C3A C2A . . 111.8(5) ?
C4A C3A C2A . . 105.9(4) ?
C6A C3A H3A . . 108.0 ?
C4A C3A H3A . . 108.0 ?
C2A C3A H3A . . 108.0 ?
C3A C4A C5A . . 102.8(4) ?
C3A C4A H401 . . 111.2 ?
C5A C4A H401 . . 111.2 ?
C3A C4A H402 . . 111.2 ?
C5A C4A H402 . . 111.2 ?
H401 C4A H402 . . 109.1 ?
N1A C5A C4A . . 102.8(4) ?
N1A C5A H501 . . 111.2 ?
C4A C5A H501 . . 111.2 ?
N1A C5A H502 . . 111.2 ?
C4A C5A H502 . . 111.2 ?
H501 C5A H502 . . 109.1 ?
F1A C6A F2A . . 106.6(5) ?
F1A C6A F3A . . 106.2(5) ?
F2A C6A F3A . . 106.8(5) ?
F1A C6A C3A . . 113.4(5) ?
F2A C6A C3A . . 111.6(5) ?
F3A C6A C3A . . 111.7(5) ?
O1A C7A O2A . . 125.7(5) ?
O1A C7A N1A . . 123.1(5) ?
O2A C7A N1A . . 111.2(5) ?
O2A C8A C9A . . 110.6(5) ?
O2A C8A C11A . . 101.4(4) ?
C9A C8A C11A . . 110.6(5) ?
O2A C8A C10A . . 109.3(5) ?
C9A C8A C10A . . 112.7(5) ?
C11A C8A C10A . . 111.7(5) ?
C8A C9A H901 . . 109.5 ?
C8A C9A H902 . . 109.5 ?
H901 C9A H902 . . 109.5 ?
C8A C9A H903 . . 109.5 ?
H901 C9A H903 . . 109.5 ?
H902 C9A H903 . . 109.5 ?
C8A C10A H10A . . 109.5 ?
C8A C10A H10B . . 109.5 ?
H10A C10A H10B . . 109.5 ?
C8A C10A H10C . . 109.5 ?
H10A C10A H10C . . 109.5 ?
H10B C10A H10C . . 109.5 ?
C8A C11A H11A . . 109.5 ?
C8A C11A H11B . . 109.5 ?
H11A C11A H11B . . 109.5 ?
C8A C11A H11C . . 109.5 ?
H11A C11A H11C . . 109.5 ?
H11B C11A H11C . . 109.5 ?
O3A C12A N2A . . 123.5(5) ?
O3A C12A C2A . . 120.2(5) ?
N2A C12A C2A . . 116.3(5) ?
N2A C13A C15A . . 109.3(5) ?
N2A C13A C14A . . 109.3(4) ?
C15A C13A C14A . . 113.9(4) ?
N2A C13A H13A . . 108.1 ?
C15A C13A H13A . . 108.1 ?
C14A C13A H13A . . 108.1 ?
C13A C14A H14A . . 109.5 ?
C13A C14A H14B . . 109.5 ?
H14A C14A H14B . . 109.5 ?
C13A C14A H14C . . 109.5 ?
H14A C14A H14C . . 109.5 ?
H14B C14A H14C . . 109.5 ?
C16A C15A C20A . . 118.0(6) ?
C16A C15A C13A . . 118.9(5) ?
C20A C15A C13A . . 123.2(5) ?
C15A C16A C17A . . 121.7(6) ?
C15A C16A H16A . . 119.2 ?
C17A C16A H16A . . 119.2 ?
C18A C17A C16A . . 119.6(6) ?
C18A C17A H17A . . 120.2 ?
C16A C17A H17A . . 120.2 ?
C19A C18A C17A . . 119.2(6) ?
C19A C18A H18A . . 120.4 ?
C17A C18A H18A . . 120.4 ?
C18A C19A C20A . . 120.3(6) ?
C18A C19A H19A . . 119.9 ?
C20A C19A H19A . . 119.9 ?
C19A C20A C15A . . 121.2(6) ?
C19A C20A H20A . . 119.4 ?
C15A C20A H20A . . 119.4 ?
C7B N1B C2B . . 119.8(5) ?
C7B N1B C5B . . 125.3(5) ?
C2B N1B C5B . . 114.9(5) ?
C12B N2B C13B . . 122.2(5) ?
C12B N2B H2 . . 122.(4) ?
C13B N2B H2 . . 115.(4) ?
N1B C2B C3B . . 103.0(5) ?
N1B C2B C12B . . 110.9(4) ?
C3B C2B C12B . . 109.5(5) ?
N1B C2B H2B . . 111.1 ?
C3B C2B H2B . . 111.1 ?
C12B C2B H2B . . 111.1 ?
C6B C3B C2B . . 111.4(6) ?
C6B C3B C4B . . 112.2(5) ?
C2B C3B C4B . . 104.1(5) ?
C6B C3B H3B . . 109.7 ?
C2B C3B H3B . . 109.7 ?
C4B C3B H3B . . 109.7 ?
C5B C4B C3B . . 105.9(6) ?
C5B C4B H411 . . 110.6 ?
C3B C4B H411 . . 110.6 ?
C5B C4B H412 . . 110.6 ?
C3B C4B H412 . . 110.6 ?
H411 C4B H412 . . 108.7 ?
N1B C5B C4B . . 102.4(5) ?
N1B C5B H511 . . 111.3 ?
C4B C5B H511 . . 111.3 ?
N1B C5B H512 . . 111.3 ?
C4B C5B H512 . . 111.3 ?
H511 C5B H512 . . 109.2 ?
F3B C6B F2B . . 105.3(6) ?
F3B C6B F1B . . 106.1(6) ?
F2B C6B F1B . . 106.2(6) ?
F3B C6B C3B . . 113.5(6) ?
F2B C6B C3B . . 112.5(6) ?
F1B C6B C3B . . 112.6(6) ?
O1B C7B N1B . . 123.2(5) ?
O1B C7B O2B . . 120.9(8) ?
N1B C7B O2B . . 115.7(8) ?
O1B C7B O2E . . 135.8(9) ?
N1B C7B O2E . . 100.0(9) ?
C7B O2B C8B . . 122.6(11) ?
O2B C8B C9B . . 111.5(14) ?
O2B C8B C10B . . 109.3(10) ?
C9B C8B C10B . . 112.2(11) ?
O2B C8B C11B . . 100.8(10) ?
C9B C8B C11B . . 112.0(11) ?
C10B C8B C11B . . 110.5(9) ?
C8B C9B H911 . . 109.5 ?
C8B C9B H912 . . 109.5 ?
H911 C9B H912 . . 109.5 ?
C8B C9B H913 . . 109.5 ?
H911 C9B H913 . . 109.5 ?
H912 C9B H913 . . 109.5 ?
C8B C10B H10I . . 109.5 ?
C8B C10B H10J . . 109.5 ?
H10I C10B H10J . . 109.5 ?
C8B C10B H10K . . 109.5 ?
H10I C10B H10K . . 109.5 ?
H10J C10B H10K . . 109.5 ?
C8B C11B H11D . . 109.5 ?
C8B C11B H11E . . 109.5 ?
H11D C11B H11E . . 109.5 ?
C8B C11B H11F . . 109.5 ?
H11D C11B H11F . . 109.5 ?
H11E C11B H11F . . 109.5 ?
C7B O2E C8E . . 115.3(13) ?
O2E C8E C11E . . 106.9(19) ?
O2E C8E C10E . . 102.7(12) ?
C11E C8E C10E . . 108.8(17) ?
O2E C8E C9E . . 108.4(14) ?
C11E C8E C9E . . 116.3(19) ?
C10E C8E C9E . . 112.7(15) ?
C8E C9E H921 . . 109.5 ?
C8E C9E H922 . . 109.5 ?
H921 C9E H922 . . 109.5 ?
C8E C9E H923 . . 109.5 ?
H921 C9E H923 . . 109.5 ?
H922 C9E H923 . . 109.5 ?
C8E C10E H10X . . 109.5 ?
C8E C10E H10Y . . 109.5 ?
H10X C10E H10Y . . 109.5 ?
C8E C10E H10Z . . 109.5 ?
H10X C10E H10Z . . 109.5 ?
H10Y C10E H10Z . . 109.5 ?
C8E C11E H11G . . 109.5 ?
C8E C11E H11H . . 109.5 ?
H11G C11E H11H . . 109.5 ?
C8E C11E H11I . . 109.5 ?
H11G C11E H11I . . 109.5 ?
H11H C11E H11I . . 109.5 ?
O3B C12B N2B . . 124.6(5) ?
O3B C12B C2B . . 120.4(5) ?
N2B C12B C2B . . 114.9(5) ?
N2B C13B C15B . . 111.9(5) ?
N2B C13B C14B . . 109.2(5) ?
C15B C13B C14B . . 110.2(5) ?
N2B C13B H13B . . 108.5 ?
C15B C13B H13B . . 108.5 ?
C14B C13B H13B . . 108.5 ?
C13B C14B H14D . . 109.5 ?
C13B C14B H14E . . 109.5 ?
H14D C14B H14E . . 109.5 ?
C13B C14B H14F . . 109.5 ?
H14D C14B H14F . . 109.5 ?
H14E C14B H14F . . 109.5 ?
C16B C15B C20B . . 119.1(5) ?
C16B C15B C13B . . 121.4(5) ?
C20B C15B C13B . . 119.5(5) ?
C15B C16B C17B . . 119.8(6) ?
C15B C16B H16B . . 120.1 ?
C17B C16B H16B . . 120.1 ?
C18B C17B C16B . . 119.8(7) ?
C18B C17B H17B . . 120.1 ?
C16B C17B H17B . . 120.1 ?
C17B C18B C19B . . 121.2(6) ?
C17B C18B H18B . . 119.4 ?
C19B C18B H18B . . 119.4 ?
C18B C19B C20B . . 119.9(7) ?
C18B C19B H19B . . 120.0 ?
C20B C19B H19B . . 120.0 ?
C15B C20B C19B . . 120.2(6) ?
C15B C20B H20B . . 119.9 ?
C19B C20B H20B . . 119.9 ?
C7C O2C C8C . . 119.2(4) ?
C7C N1C C5C . . 119.8(5) ?
C7C N1C C2C . . 126.0(4) ?
C5C N1C C2C . . 114.2(4) ?
C12C N2C C13C . . 120.0(5) ?
C12C N2C H3 . . 123.(3) ?
C13C N2C H3 . . 117.(3) ?
N1C C2C C12C . . 111.8(4) ?
N1C C2C C3C . . 100.6(4) ?
C12C C2C C3C . . 109.6(4) ?
N1C C2C H2C . . 111.4 ?
C12C C2C H2C . . 111.4 ?
C3C C2C H2C . . 111.4 ?
C6C C3C C4C . . 114.1(5) ?
C6C C3C C2C . . 113.5(4) ?
C4C C3C C2C . . 105.3(4) ?
C6C C3C H3C . . 107.9 ?
C4C C3C H3C . . 107.9 ?
C2C C3C H3C . . 107.9 ?
C5C C4C C3C . . 103.2(4) ?
C5C C4C H431 . . 111.1 ?
C3C C4C H431 . . 111.1 ?
C5C C4C H432 . . 111.1 ?
C3C C4C H432 . . 111.1 ?
H431 C4C H432 . . 109.1 ?
N1C C5C C4C . . 102.1(4) ?
N1C C5C H531 . . 111.3 ?
C4C C5C H531 . . 111.3 ?
N1C C5C H532 . . 111.3 ?
C4C C5C H532 . . 111.3 ?
H531 C5C H532 . . 109.2 ?
F3C C6C F1C . . 107.3(5) ?
F3C C6C F2C . . 106.8(5) ?
F1C C6C F2C . . 107.1(5) ?
F3C C6C C3C . . 113.3(5) ?
F1C C6C C3C . . 110.4(5) ?
F2C C6C C3C . . 111.5(5) ?
O1C C7C N1C . . 124.6(5) ?
O1C C7C O2C . . 124.7(5) ?
N1C C7C O2C . . 110.7(5) ?
O2C C8C C11C . . 110.5(5) ?
O2C C8C C10C . . 110.0(5) ?
C11C C8C C10C . . 113.6(5) ?
O2C C8C C9C . . 102.0(4) ?
C11C C8C C9C . . 109.9(5) ?
C10C C8C C9C . . 110.2(5) ?
C8C C9C H931 . . 109.5 ?
C8C C9C H932 . . 109.5 ?
H931 C9C H932 . . 109.5 ?
C8C C9C H933 . . 109.5 ?
H931 C9C H933 . . 109.5 ?
H932 C9C H933 . . 109.5 ?
C8C C10C H10P . . 109.5 ?
C8C C10C H10R . . 109.5 ?
H10P C10C H10R . . 109.5 ?
C8C C10C H10S . . 109.5 ?
H10P C10C H10S . . 109.5 ?
H10R C10C H10S . . 109.5 ?
C8C C11C H11X . . 109.5 ?
C8C C11C H11Y . . 109.5 ?
H11X C11C H11Y . . 109.5 ?
C8C C11C H11Z . . 109.5 ?
H11X C11C H11Z . . 109.5 ?
H11Y C11C H11Z . . 109.5 ?
O3C C12C N2C . . 123.1(5) ?
O3C C12C C2C . . 120.7(5) ?
N2C C12C C2C . . 116.1(5) ?
N2C C13C C15C . . 110.9(4) ?
N2C C13C C14C . . 110.5(5) ?
C15C C13C C14C . . 113.5(5) ?
N2C C13C H13C . . 107.2 ?
C15C C13C H13C . . 107.2 ?
C14C C13C H13C . . 107.2 ?
C13C C14C H14G . . 109.5 ?
C13C C14C H14H . . 109.5 ?
H14G C14C H14H . . 109.5 ?
C13C C14C H14I . . 109.5 ?
H14G C14C H14I . . 109.5 ?
H14H C14C H14I . . 109.5 ?
C16C C15C C20C . . 117.5(5) ?
C16C C15C C13C . . 119.6(5) ?
C20C C15C C13C . . 122.9(5) ?
C15C C16C C17C . . 121.6(5) ?
C15C C16C H16C . . 119.2 ?
C17C C16C H16C . . 119.2 ?
C18C C17C C16C . . 120.0(6) ?
C18C C17C H17C . . 120.0 ?
C16C C17C H17C . . 120.0 ?
C17C C18C C19C . . 118.9(6) ?
C17C C18C H18C . . 120.5 ?
C19C C18C H18C . . 120.5 ?
C20C C19C C18C . . 120.5(5) ?
C20C C19C H19C . . 119.7 ?
C18C C19C H19C . . 119.7 ?
C19C C20C C15C . . 121.3(6) ?
C19C C20C H20C . . 119.3 ?
C15C C20C H20C . . 119.3 ?
C7D N1D C2D . . 119.7(5) ?
C7D N1D C5D . . 125.4(5) ?
C2D N1D C5D . . 114.0(5) ?
C12D N2D C13D . . 123.5(4) ?
C12D N2D H4 . . 119.(2) ?
C13D N2D H4 . . 117.(2) ?
N1D C2D C12D . . 112.6(4) ?
N1D C2D C3D . . 102.8(4) ?
C12D C2D C3D . . 109.1(4) ?
N1D C2D H2D . . 110.7 ?
C12D C2D H2D . . 110.7 ?
C3D C2D H2D . . 110.7 ?
C6D C3D C4D . . 113.7(5) ?
C6D C3D C2D . . 111.3(5) ?
C4D C3D C2D . . 103.7(5) ?
C6D C3D H3D . . 109.3 ?
C4D C3D H3D . . 109.3 ?
C2D C3D H3D . . 109.3 ?
C3D C4D C5D . . 104.3(5) ?
C3D C4D H441 . . 110.9 ?
C5D C4D H441 . . 110.9 ?
C3D C4D H442 . . 110.9 ?
C5D C4D H442 . . 110.9 ?
H441 C4D H442 . . 108.9 ?
N1D C5D C4D . . 103.1(5) ?
N1D C5D H541 . . 111.1 ?
C4D C5D H541 . . 111.1 ?
N1D C5D H542 . . 111.1 ?
C4D C5D H542 . . 111.1 ?
H541 C5D H542 . . 109.1 ?
F3D C6D F2D . . 106.6(5) ?
F3D C6D F1D . . 106.9(6) ?
F2D C6D F1D . . 106.5(5) ?
F3D C6D C3D . . 112.3(5) ?
F2D C6D C3D . . 111.3(6) ?
F1D C6D C3D . . 112.9(5) ?
O1D C7D N1D . . 123.5(5) ?
O1D C7D O2D . . 126.8(6) ?
N1D C7D O2D . . 109.7(5) ?
C7D O2D C8D . . 120.0(5) ?
O2D C8D C9D . . 109.6(5) ?
O2D C8D C10D . . 108.5(6) ?
C9D C8D C10D . . 114.7(8) ?
O2D C8D C11D . . 101.8(7) ?
C9D C8D C11D . . 109.6(6) ?
C10D C8D C11D . . 111.8(7) ?
C8D C9D H941 . . 109.5 ?
C8D C9D H942 . . 109.5 ?
H941 C9D H942 . . 109.5 ?
C8D C9D H943 . . 109.5 ?
H941 C9D H943 . . 109.5 ?
H942 C9D H943 . . 109.5 ?
C8D C10D H10L . . 109.5 ?
C8D C10D H10M . . 109.5 ?
H10L C10D H10M . . 109.5 ?
C8D C10D H10N . . 109.5 ?
H10L C10D H10N . . 109.5 ?
H10M C10D H10N . . 109.5 ?
C8D C11D H11J . . 109.5 ?
C8D C11D H11K . . 109.5 ?
H11J C11D H11K . . 109.5 ?
C8D C11D H11L . . 109.5 ?
H11J C11D H11L . . 109.5 ?
H11K C11D H11L . . 109.5 ?
O3D C12D N2D . . 124.8(5) ?
O3D C12D C2D . . 121.9(5) ?
N2D C12D C2D . . 113.1(4) ?
N2D C13D C14D . . 109.1(5) ?
N2D C13D C15D . . 111.8(5) ?
C14D C13D C15D . . 112.2(5) ?
N2D C13D H13D . . 107.9 ?
C14D C13D H13D . . 107.9 ?
C15D C13D H13D . . 107.9 ?
C13D C14D H14J . . 109.5 ?
C13D C14D H14K . . 109.5 ?
H14J C14D H14K . . 109.5 ?
C13D C14D H14L . . 109.5 ?
H14J C14D H14L . . 109.5 ?
H14K C14D H14L . . 109.5 ?
C16D C15D C20D . . 118.6(6) ?
C16D C15D C13D . . 122.1(5) ?
C20D C15D C13D . . 119.2(5) ?
C15D C16D C17D . . 120.7(5) ?
C15D C16D H16D . . 119.6 ?
C17D C16D H16D . . 119.6 ?
C18D C17D C16D . . 120.2(6) ?
C18D C17D H17D . . 119.9 ?
C16D C17D H17D . . 119.9 ?
C17D C18D C19D . . 119.2(6) ?
C17D C18D H18D . . 120.4 ?
C19D C18D H18D . . 120.4 ?
C20D C19D C18D . . 120.4(5) ?
C20D C19D H19D . . 119.8 ?
C18D C19D H19D . . 119.8 ?
C19D C20D C15D . . 120.8(6) ?
C19D C20D H20D . . 119.6 ?
C15D C20D H20D . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7A N1A C2A C12A . . . . -57.7(6) ?
C5A N1A C2A C12A . . . . 116.2(5) ?
C7A N1A C2A C3A . . . . -176.6(5) ?
C5A N1A C2A C3A . . . . -2.6(6) ?
N1A C2A C3A C6A . . . . -145.8(5) ?
C12A C2A C3A C6A . . . . 96.5(6) ?
N1A C2A C3A C4A . . . . -19.9(6) ?
C12A C2A C3A C4A . . . . -137.5(5) ?
C6A C3A C4A C5A . . . . 158.0(5) ?
C2A C3A C4A C5A . . . . 34.1(6) ?
C7A N1A C5A C4A . . . . -163.2(6) ?
C2A N1A C5A C4A . . . . 23.7(6) ?
C3A C4A C5A N1A . . . . -34.5(6) ?
C4A C3A C6A F1A . . . . -58.6(7) ?
C2A C3A C6A F1A . . . . 62.2(6) ?
C4A C3A C6A F2A . . . . 61.9(7) ?
C2A C3A C6A F2A . . . . -177.3(5) ?
C4A C3A C6A F3A . . . . -178.6(5) ?
C2A C3A C6A F3A . . . . -57.8(7) ?
C8A O2A C7A O1A . . . . 1.9(9) ?
C8A O2A C7A N1A . . . . -178.2(5) ?
C5A N1A C7A O1A . . . . 176.8(6) ?
C2A N1A C7A O1A . . . . -10.4(9) ?
C5A N1A C7A O2A . . . . -3.2(8) ?
C2A N1A C7A O2A . . . . 169.7(4) ?
C7A O2A C8A C9A . . . . 58.0(7) ?
C7A O2A C8A C11A . . . . 175.4(5) ?
C7A O2A C8A C10A . . . . -66.6(6) ?
C13A N2A C12A O3A . . . . 4.3(7) ?
C13A N2A C12A C2A . . . . -175.8(4) ?
N1A C2A C12A O3A . . . . -53.6(6) ?
C3A C2A C12A O3A . . . . 59.1(6) ?
N1A C2A C12A N2A . . . . 126.4(5) ?
C3A C2A C12A N2A . . . . -120.9(5) ?
C12A N2A C13A C15A . . . . -161.4(5) ?
C12A N2A C13A C14A . . . . 73.4(6) ?
N2A C13A C15A C16A . . . . 95.4(6) ?
C14A C13A C15A C16A . . . . -142.1(6) ?
N2A C13A C15A C20A . . . . -84.2(6) ?
C14A C13A C15A C20A . . . . 38.2(8) ?
C20A C15A C16A C17A . . . . -3.1(9) ?
C13A C15A C16A C17A . . . . 177.3(6) ?
C15A C16A C17A C18A . . . . 2.3(10) ?
C16A C17A C18A C19A . . . . -0.5(10) ?
C17A C18A C19A C20A . . . . -0.4(10) ?
C18A C19A C20A C15A . . . . -0.5(10) ?
C16A C15A C20A C19A . . . . 2.2(9) ?
C13A C15A C20A C19A . . . . -178.2(6) ?
C7B N1B C2B C3B . . . . 170.1(5) ?
C5B N1B C2B C3B . . . . -10.7(7) ?
C7B N1B C2B C12B . . . . -72.8(6) ?
C5B N1B C2B C12B . . . . 106.3(6) ?
N1B C2B C3B C6B . . . . -95.6(6) ?
C12B C2B C3B C6B . . . . 146.4(5) ?
N1B C2B C3B C4B . . . . 25.5(6) ?
C12B C2B C3B C4B . . . . -92.4(6) ?
C6B C3B C4B C5B . . . . 88.5(7) ?
C2B C3B C4B C5B . . . . -32.1(7) ?
C7B N1B C5B C4B . . . . 170.1(6) ?
C2B N1B C5B C4B . . . . -9.0(7) ?
C3B C4B C5B N1B . . . . 25.0(7) ?
C2B C3B C6B F3B . . . . -62.8(8) ?
C4B C3B C6B F3B . . . . -179.1(6) ?
C2B C3B C6B F2B . . . . 177.8(6) ?
C4B C3B C6B F2B . . . . 61.5(8) ?
C2B C3B C6B F1B . . . . 57.8(7) ?
C4B C3B C6B F1B . . . . -58.5(8) ?
C2B N1B C7B O1B . . . . 2.7(9) ?
C5B N1B C7B O1B . . . . -176.4(6) ?
C2B N1B C7B O2B . . . . -172.5(9) ?
C5B N1B C7B O2B . . . . 8.5(11) ?
C2B N1B C7B O2E . . . . 173.0(9) ?
C5B N1B C7B O2E . . . . -6.1(11) ?
O1B C7B O2B C8B . . . . 4.4(17) ?
N1B C7B O2B C8B . . . . 179.6(10) ?
C7B O2B C8B C9B . . . . 61.5(17) ?
C7B O2B C8B C10B . . . . -63.1(15) ?
C7B O2B C8B C11B . . . . -179.5(11) ?
O1B C7B O2E C8E . . . . -22.(2) ?
N1B C7B O2E C8E . . . . 169.1(13) ?
C7B O2E C8E C11E . . . . 69.(2) ?
C7B O2E C8E C10E . . . . -176.3(14) ?
C7B O2E C8E C9E . . . . -56.8(19) ?
C13B N2B C12B O3B . . . . -4.0(8) ?
C13B N2B C12B C2B . . . . 172.5(5) ?
N1B C2B C12B O3B . . . . -48.4(7) ?
C3B C2B C12B O3B . . . . 64.6(7) ?
N1B C2B C12B N2B . . . . 135.0(5) ?
C3B C2B C12B N2B . . . . -112.0(6) ?
C12B N2B C13B C15B . . . . -89.1(6) ?
C12B N2B C13B C14B . . . . 148.6(5) ?
N2B C13B C15B C16B . . . . -36.8(8) ?
C14B C13B C15B C16B . . . . 84.9(7) ?
N2B C13B C15B C20B . . . . 145.1(5) ?
C14B C13B C15B C20B . . . . -93.2(6) ?
C20B C15B C16B C17B . . . . -0.9(9) ?
C13B C15B C16B C17B . . . . -178.9(6) ?
C15B C16B C17B C18B . . . . 1.4(10) ?
C16B C17B C18B C19B . . . . -0.4(11) ?
C17B C18B C19B C20B . . . . -1.0(10) ?
C16B C15B C20B C19B . . . . -0.6(8) ?
C13B C15B C20B C19B . . . . 177.5(5) ?
C18B C19B C20B C15B . . . . 1.5(9) ?
C7C N1C C2C C12C . . . . -63.3(7) ?
C5C N1C C2C C12C . . . . 117.5(5) ?
C7C N1C C2C C3C . . . . -179.6(5) ?
C5C N1C C2C C3C . . . . 1.2(6) ?
N1C C2C C3C C6C . . . . -149.3(5) ?
C12C C2C C3C C6C . . . . 92.8(6) ?
N1C C2C C3C C4C . . . . -23.8(5) ?
C12C C2C C3C C4C . . . . -141.7(4) ?
C6C C3C C4C C5C . . . . 162.8(5) ?
C2C C3C C4C C5C . . . . 37.7(5) ?
C7C N1C C5C C4C . . . . -157.5(5) ?
C2C N1C C5C C4C . . . . 21.8(6) ?
C3C C4C C5C N1C . . . . -35.5(6) ?
C4C C3C C6C F3C . . . . -63.8(6) ?
C2C C3C C6C F3C . . . . 56.8(7) ?
C4C C3C C6C F1C . . . . 56.6(7) ?
C2C C3C C6C F1C . . . . 177.3(5) ?
C4C C3C C6C F2C . . . . 175.6(5) ?
C2C C3C C6C F2C . . . . -63.7(6) ?
C5C N1C C7C O1C . . . . -0.6(9) ?
C2C N1C C7C O1C . . . . -179.8(5) ?
C5C N1C C7C O2C . . . . -179.3(5) ?
C2C N1C C7C O2C . . . . 1.5(8) ?
C8C O2C C7C O1C . . . . 3.3(8) ?
C8C O2C C7C N1C . . . . -177.9(5) ?
C7C O2C C8C C11C . . . . 60.6(6) ?
C7C O2C C8C C10C . . . . -65.6(7) ?
C7C O2C C8C C9C . . . . 177.4(5) ?
C13C N2C C12C O3C . . . . 0.1(7) ?
C13C N2C C12C C2C . . . . 177.4(4) ?
N1C C2C C12C O3C . . . . -42.2(6) ?
C3C C2C C12C O3C . . . . 68.5(6) ?
N1C C2C C12C N2C . . . . 140.5(4) ?
C3C C2C C12C N2C . . . . -108.8(5) ?
C12C N2C C13C C15C . . . . -154.5(4) ?
C12C N2C C13C C14C . . . . 78.7(6) ?
N2C C13C C15C C16C . . . . 99.2(6) ?
C14C C13C C15C C16C . . . . -135.7(6) ?
N2C C13C C15C C20C . . . . -82.1(6) ?
C14C C13C C15C C20C . . . . 43.0(8) ?
C20C C15C C16C C17C . . . . -1.0(9) ?
C13C C15C C16C C17C . . . . 177.8(6) ?
C15C C16C C17C C18C . . . . -0.2(10) ?
C16C C17C C18C C19C . . . . 1.1(10) ?
C17C C18C C19C C20C . . . . -0.8(10) ?
C18C C19C C20C C15C . . . . -0.4(9) ?
C16C C15C C20C C19C . . . . 1.3(8) ?
C13C C15C C20C C19C . . . . -177.4(5) ?
C7D N1D C2D C12D . . . . -85.4(6) ?
C5D N1D C2D C12D . . . . 105.1(6) ?
C7D N1D C2D C3D . . . . 157.5(5) ?
C5D N1D C2D C3D . . . . -12.1(6) ?
N1D C2D C3D C6D . . . . -93.8(5) ?
C12D C2D C3D C6D . . . . 146.5(5) ?
N1D C2D C3D C4D . . . . 28.8(5) ?
C12D C2D C3D C4D . . . . -90.8(5) ?
C6D C3D C4D C5D . . . . 85.9(6) ?
C2D C3D C4D C5D . . . . -35.2(6) ?
C7D N1D C5D C4D . . . . -178.4(5) ?
C2D N1D C5D C4D . . . . -9.5(6) ?
C3D C4D C5D N1D . . . . 27.6(6) ?
C4D C3D C6D F3D . . . . 179.2(6) ?
C2D C3D C6D F3D . . . . -64.1(7) ?
C4D C3D C6D F2D . . . . 59.8(7) ?
C2D C3D C6D F2D . . . . 176.5(5) ?
C4D C3D C6D F1D . . . . -59.9(8) ?
C2D C3D C6D F1D . . . . 56.8(7) ?
C2D N1D C7D O1D . . . . 7.2(8) ?
C5D N1D C7D O1D . . . . 175.5(5) ?
C2D N1D C7D O2D . . . . -173.9(4) ?
C5D N1D C7D O2D . . . . -5.6(7) ?
O1D C7D O2D C8D . . . . -7.1(8) ?
N1D C7D O2D C8D . . . . 174.0(5) ?
C7D O2D C8D C9D . . . . 65.4(8) ?
C7D O2D C8D C10D . . . . -60.5(8) ?
C7D O2D C8D C11D . . . . -178.6(5) ?
C13D N2D C12D O3D . . . . -7.3(9) ?
C13D N2D C12D C2D . . . . 169.4(5) ?
N1D C2D C12D O3D . . . . -38.2(7) ?
C3D C2D C12D O3D . . . . 75.2(6) ?
N1D C2D C12D N2D . . . . 145.0(5) ?
C3D C2D C12D N2D . . . . -101.6(5) ?
C12D N2D C13D C14D . . . . 132.2(6) ?
C12D N2D C13D C15D . . . . -103.1(6) ?
N2D C13D C15D C16D . . . . -17.3(8) ?
C14D C13D C15D C16D . . . . 105.6(6) ?
N2D C13D C15D C20D . . . . 164.0(5) ?
C14D C13D C15D C20D . . . . -73.1(7) ?
C20D C15D C16D C17D . . . . -1.1(9) ?
C13D C15D C16D C17D . . . . -179.8(6) ?
C15D C16D C17D C18D . . . . -0.1(10) ?
C16D C17D C18D C19D . . . . 0.9(10) ?
C17D C18D C19D C20D . . . . -0.4(10) ?
C18D C19D C20D C15D . . . . -0.8(10) ?
C16D C15D C20D C19D . . . . 1.5(9) ?
C13D C15D C20D C19D . . . . -179.8(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2A H1 O3B 1_455 0.93(7) 1.94(7) 2.845(6) 163.(5) ?
C2A H2A O3B 1_455 1.0 2.41 3.289(7) 146.0 ?
C4A H402 F2B 1_556 0.99 2.52 3.255(7) 131.2 ?
C13A H13A F3B . 1.0 2.63 3.566(7) 154.9 ?
N2B H2 O3A . 0.86(6) 1.99(6) 2.832(6) 167.(6) ?
N2C H3 O3D . 0.93(5) 1.93(6) 2.859(6) 174.(5) ?
N2D H4 O3C 1_556 1.00(5) 1.80(5) 2.792(5) 171.(4) ?
C5D H541 F2C . 0.99 2.54 3.369(7) 141.4 ?

####################################################################### 
# 
# 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_haf8921
_database_code_depnum_ccdc_archive 'CCDC 1855497'
_audit_update_record             
;
2018-07-12 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H25 F3 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         386.41
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.9485(2)
_cell_length_b                   11.2537(3)
_cell_length_c                   19.5558(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1969.34(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      4.5221
_cell_measurement_theta_max      68.1453
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.048
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816

_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            22784
_diffrn_reflns_av_R_equivalents  0.0671
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_theta_min         4.52
_diffrn_reflns_theta_max         68.26
_diffrn_reflns_theta_full        68.26
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23

_refine_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.
;

_reflns_number_total             3580
_reflns_number_gt                3292
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0749
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_refine_ls_number_reflns         3580
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+0.2852P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.206
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1258 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(7)

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

_computing_data_collection       
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.6189(2) 1.04797(14) 0.66208(8) 0.0311(4) Uani d . . . 1 . .
F F2 0.46512(19) 1.02210(13) 0.57872(7) 0.0235(4) Uani d . . . 1 . .
F F3 0.69636(18) 0.96978(14) 0.56777(7) 0.0233(4) Uani d . . . 1 . .
N N1 0.4436(2) 0.66329(18) 0.63307(9) 0.0130(4) Uani d . . . 1 . .
N N2 0.4945(3) 0.81981(18) 0.47312(10) 0.0120(4) Uani d . . . 1 . .
H H1A 0.576(4) 0.805(3) 0.4707(15) 0.017(8) Uiso d . . . 1 . .
O O1 0.28187(19) 0.79641(15) 0.53499(9) 0.0156(4) Uani d . . . 1 . .
O O2 0.4139(2) 0.47267(15) 0.66825(8) 0.0189(4) Uani d . . . 1 . .
O O3 0.5128(2) 0.51747(14) 0.56314(8) 0.0151(4) Uani d . . . 1 . .
C C2 0.5183(3) 0.7497(2) 0.58886(12) 0.0126(5) Uani d . . . 1 . .
H H2 0.6149 0.7168 0.5715 0.015 Uiso calc U . R 1 . .
C C3 0.5474(3) 0.8511(2) 0.64084(11) 0.0138(5) Uani d . . . 1 . .
H H3 0.6358 0.8268 0.6688 0.017 Uiso calc U . R 1 . .
C C4 0.4113(3) 0.8472(2) 0.68813(12) 0.0178(6) Uani d . . . 1 . .
H H4A 0.4322 0.8869 0.7323 0.021 Uiso calc U . R 1 . .
H H4B 0.3232 0.885 0.6665 0.021 Uiso calc U . R 1 . .
C C5 0.3875(3) 0.7138(2) 0.69764(12) 0.0168(6) Uani d . . . 1 . .
H H5A 0.4451 0.6836 0.7372 0.02 Uiso calc U . R 1 . .
H H5B 0.2804 0.6951 0.7043 0.02 Uiso calc U . R 1 . .
C C6 0.5814(3) 0.9717(2) 0.61218(12) 0.0183(6) Uani d . . . 1 . .
C C12 0.4190(3) 0.7882(2) 0.52923(12) 0.0116(5) Uani d . . . 1 . .
C C13 0.4298(3) 0.8903(2) 0.41818(11) 0.0136(5) Uani d . . . 1 . .
H H13 0.3321 0.9224 0.4347 0.016 Uiso calc U . R 1 . .
C C14 0.5328(3) 0.9960(2) 0.40387(12) 0.0183(6) Uani d . . . 1 . .
H H14A 0.5438 1.0436 0.4455 0.027 Uiso calc U . R 1 . .
H H14B 0.4894 1.0452 0.3676 0.027 Uiso calc U . R 1 . .
H H14C 0.631 0.967 0.3893 0.027 Uiso calc U . R 1 . .
C C15 0.4003(3) 0.8210(2) 0.35263(12) 0.0142(5) Uani d . . . 1 . .
C C16 0.3146(3) 0.8748(2) 0.30168(12) 0.0175(6) Uani d . . . 1 . .
H H16 0.2743 0.9519 0.3091 0.021 Uiso calc U . R 1 . .
C C17 0.2877(3) 0.8166(3) 0.24007(13) 0.0231(6) Uani d . . . 1 . .
H H17 0.2295 0.8539 0.2056 0.028 Uiso calc U . R 1 . .
C C18 0.3459(3) 0.7043(3) 0.22920(14) 0.0259(6) Uani d . . . 1 . .
H H18 0.3275 0.6641 0.1873 0.031 Uiso calc U . R 1 . .
C C19 0.4313(3) 0.6505(3) 0.27971(14) 0.0247(6) Uani d . . . 1 . .
H H19 0.4711 0.5733 0.2722 0.03 Uiso calc U . R 1 . .
C C20 0.4592(3) 0.7084(2) 0.34115(13) 0.0185(6) Uani d . . . 1 . .
H H20 0.5184 0.6711 0.3753 0.022 Uiso calc U . R 1 . .
C C7 0.4542(3) 0.5440(2) 0.62522(12) 0.0137(5) Uani d . . . 1 . .
C C8 0.5333(3) 0.3928(2) 0.54216(12) 0.0156(5) Uani d . . . 1 . .
C C9 0.6502(3) 0.3338(2) 0.58729(14) 0.0210(6) Uani d . . . 1 . .
H H9A 0.744 0.3786 0.5846 0.032 Uiso calc U . R 1 . .
H H9B 0.6671 0.2522 0.5716 0.032 Uiso calc U . R 1 . .
H H9C 0.6149 0.3326 0.6347 0.032 Uiso calc U . R 1 . .
C C10 0.3861(3) 0.3257(2) 0.54346(14) 0.0215(6) Uani d . . . 1 . .
H H10A 0.3557 0.3123 0.591 0.032 Uiso calc U . R 1 . .
H H10B 0.3982 0.2491 0.5203 0.032 Uiso calc U . R 1 . .
H H10C 0.3093 0.3725 0.52 0.032 Uiso calc U . R 1 . .
C C11 0.5886(3) 0.4069(2) 0.46872(13) 0.0220(6) Uani d . . . 1 . .
H H11A 0.5098 0.4432 0.4409 0.033 Uiso calc U . R 1 . .
H H11B 0.6138 0.3286 0.45 0.033 Uiso calc U . R 1 . .
H H11C 0.6774 0.4577 0.4682 0.033 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C6 . 1.343(3) ?
F2 C6 . 1.354(3) ?
F3 C6 . 1.347(3) ?
N1 C7 . 1.355(3) ?
N1 C2 . 1.463(3) ?
N1 C5 . 1.473(3) ?
N2 C12 . 1.337(3) ?
N2 C13 . 1.456(3) ?
N2 H1A . 0.75(3) ?
O1 C12 . 1.236(3) ?
O2 C7 . 1.218(3) ?
O3 C7 . 1.355(3) ?
O3 C8 . 1.473(3) ?
C2 C12 . 1.529(3) ?
C2 C3 . 1.550(3) ?
C2 H2 . 1.0 ?
C3 C6 . 1.499(4) ?
C3 C4 . 1.530(3) ?
C3 H3 . 1.0 ?
C4 C5 . 1.527(4) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C13 C15 . 1.524(3) ?
C13 C14 . 1.530(4) ?
C13 H13 . 1.0 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 C20 . 1.391(4) ?
C15 C16 . 1.395(4) ?
C16 C17 . 1.392(4) ?
C16 H16 . 0.95 ?
C17 C18 . 1.384(4) ?
C17 H17 . 0.95 ?
C18 C19 . 1.388(4) ?
C18 H18 . 0.95 ?
C19 C20 . 1.389(4) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C8 C10 . 1.518(4) ?
C8 C9 . 1.521(4) ?
C8 C11 . 1.527(3) ?
C9 H9A . 0.98 ?
C9 H9B . 0.98 ?
C9 H9C . 0.98 ?
C10 H10A . 0.98 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 N1 C2 . . 124.0(2) ?
C7 N1 C5 . . 120.3(2) ?
C2 N1 C5 . . 113.92(19) ?
C12 N2 C13 . . 123.4(2) ?
C12 N2 H1A . . 119.(2) ?
C13 N2 H1A . . 117.(2) ?
C7 O3 C8 . . 120.47(18) ?
N1 C2 C12 . . 111.9(2) ?
N1 C2 C3 . . 100.28(18) ?
C12 C2 C3 . . 112.94(19) ?
N1 C2 H2 . . 110.4 ?
C12 C2 H2 . . 110.4 ?
C3 C2 H2 . . 110.4 ?
C6 C3 C4 . . 114.4(2) ?
C6 C3 C2 . . 117.07(19) ?
C4 C3 C2 . . 104.0(2) ?
C6 C3 H3 . . 106.9 ?
C4 C3 H3 . . 106.9 ?
C2 C3 H3 . . 106.9 ?
C5 C4 C3 . . 102.2(2) ?
C5 C4 H4A . . 111.3 ?
C3 C4 H4A . . 111.3 ?
C5 C4 H4B . . 111.3 ?
C3 C4 H4B . . 111.3 ?
H4A C4 H4B . . 109.2 ?
N1 C5 C4 . . 103.17(19) ?
N1 C5 H5A . . 111.1 ?
C4 C5 H5A . . 111.1 ?
N1 C5 H5B . . 111.1 ?
C4 C5 H5B . . 111.1 ?
H5A C5 H5B . . 109.1 ?
F1 C6 F3 . . 106.7(2) ?
F1 C6 F2 . . 106.0(2) ?
F3 C6 F2 . . 106.39(19) ?
F1 C6 C3 . . 110.98(19) ?
F3 C6 C3 . . 112.4(2) ?
F2 C6 C3 . . 113.8(2) ?
O1 C12 N2 . . 123.8(2) ?
O1 C12 C2 . . 121.9(2) ?
N2 C12 C2 . . 114.1(2) ?
N2 C13 C15 . . 114.2(2) ?
N2 C13 C14 . . 108.7(2) ?
C15 C13 C14 . . 110.39(19) ?
N2 C13 H13 . . 107.8 ?
C15 C13 H13 . . 107.8 ?
C14 C13 H13 . . 107.8 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C20 C15 C16 . . 119.2(2) ?
C20 C15 C13 . . 122.5(2) ?
C16 C15 C13 . . 118.3(2) ?
C17 C16 C15 . . 120.6(3) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C18 C17 C16 . . 119.8(3) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C17 C18 C19 . . 119.8(2) ?
C17 C18 H18 . . 120.1 ?
C19 C18 H18 . . 120.1 ?
C18 C19 C20 . . 120.6(3) ?
C18 C19 H19 . . 119.7 ?
C20 C19 H19 . . 119.7 ?
C19 C20 C15 . . 119.9(2) ?
C19 C20 H20 . . 120.0 ?
C15 C20 H20 . . 120.0 ?
O2 C7 N1 . . 123.6(2) ?
O2 C7 O3 . . 126.1(2) ?
N1 C7 O3 . . 110.3(2) ?
O3 C8 C10 . . 111.1(2) ?
O3 C8 C9 . . 109.9(2) ?
C10 C8 C9 . . 111.7(2) ?
O3 C8 C11 . . 101.75(19) ?
C10 C8 C11 . . 110.4(2) ?
C9 C8 C11 . . 111.6(2) ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
C8 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C8 C11 H11A . . 109.5 ?
C8 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C8 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 N1 C2 C12 . . . . 91.9(3) ?
C5 N1 C2 C12 . . . . -103.3(2) ?
C7 N1 C2 C3 . . . . -148.1(2) ?
C5 N1 C2 C3 . . . . 16.7(3) ?
N1 C2 C3 C6 . . . . -162.1(2) ?
C12 C2 C3 C6 . . . . -42.9(3) ?
N1 C2 C3 C4 . . . . -34.9(2) ?
C12 C2 C3 C4 . . . . 84.4(2) ?
C6 C3 C4 C5 . . . . 169.7(2) ?
C2 C3 C4 C5 . . . . 40.8(2) ?
C7 N1 C5 C4 . . . . 173.5(2) ?
C2 N1 C5 C4 . . . . 8.1(3) ?
C3 C4 C5 N1 . . . . -29.7(3) ?
C4 C3 C6 F1 . . . . 64.2(3) ?
C2 C3 C6 F1 . . . . -173.8(2) ?
C4 C3 C6 F3 . . . . -176.3(2) ?
C2 C3 C6 F3 . . . . -54.3(3) ?
C4 C3 C6 F2 . . . . -55.3(3) ?
C2 C3 C6 F2 . . . . 66.7(3) ?
C13 N2 C12 O1 . . . . 13.5(4) ?
C13 N2 C12 C2 . . . . -161.7(2) ?
N1 C2 C12 O1 . . . . 33.7(3) ?
C3 C2 C12 O1 . . . . -78.6(3) ?
N1 C2 C12 N2 . . . . -151.0(2) ?
C3 C2 C12 N2 . . . . 96.7(2) ?
C12 N2 C13 C15 . . . . -108.4(3) ?
C12 N2 C13 C14 . . . . 127.8(2) ?
N2 C13 C15 C20 . . . . -13.3(3) ?
C14 C13 C15 C20 . . . . 109.5(3) ?
N2 C13 C15 C16 . . . . 168.7(2) ?
C14 C13 C15 C16 . . . . -68.5(3) ?
C20 C15 C16 C17 . . . . 0.2(4) ?
C13 C15 C16 C17 . . . . 178.3(2) ?
C15 C16 C17 C18 . . . . 0.2(4) ?
C16 C17 C18 C19 . . . . -0.2(4) ?
C17 C18 C19 C20 . . . . -0.1(5) ?
C18 C19 C20 C15 . . . . 0.5(4) ?
C16 C15 C20 C19 . . . . -0.5(4) ?
C13 C15 C20 C19 . . . . -178.5(2) ?
C2 N1 C7 O2 . . . . 166.9(2) ?
C5 N1 C7 O2 . . . . 3.1(4) ?
C2 N1 C7 O3 . . . . -14.1(3) ?
C5 N1 C7 O3 . . . . -178.0(2) ?
C8 O3 C7 O2 . . . . -0.2(4) ?
C8 O3 C7 N1 . . . . -179.1(2) ?
C7 O3 C8 C10 . . . . 58.2(3) ?
C7 O3 C8 C9 . . . . -66.0(3) ?
C7 O3 C8 C11 . . . . 175.7(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H1A O1 4_566 0.75(3) 2.17(3) 2.890(3) 161.(3) ?
C2 H2 O1 4_566 1.0 2.57 3.420(3) 143.1 ?
C4 H4A O2 3_656 0.99 2.57 3.511(3) 158.5 ?

