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

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

data_dan9433_2S3S-5a
_database_code_depnum_ccdc_archive 'CCDC 2193973'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-08-01 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H25 F3 N2 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         402.41
_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                   9.6310(2)
_cell_length_b                   19.7773(4)
_cell_length_c                   20.8690(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3975.03(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9859
_cell_measurement_theta_min      3.0785
_cell_measurement_theta_max      70.3012
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.452
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.075
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696

_exptl_absorpt_coefficient_mu    0.962
_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  0.73
_exptl_absorpt_correction_T_max  0.93

_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            36574
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_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.

The hydrogen atoms at N2A, N2B, O4A and O4B were refined
freely
;

_reflns_number_total             7012
_reflns_number_gt                6567
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_gt          0.0757
_refine_ls_wR_factor_ref         0.0779
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_number_reflns         7012
_refine_ls_number_parameters     527
_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)+(0.0350P)²+0.6770P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.205
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 2702 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)

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
N N1A 0.9269(2) 0.81189(10) 0.79549(9) 0.0152(4) Uani d . . . 1 . .
N N2A 0.9677(2) 0.67084(10) 0.68771(9) 0.0141(4) Uani d . . . 1 . .
H H2C 1.052(3) 0.6650(15) 0.6981(13) 0.019(7) Uiso d . . . 1 . .
O O1A 0.93563(17) 0.92405(8) 0.77189(8) 0.0191(4) Uani d . . . 1 . .
O O2A 1.01340(17) 0.84341(8) 0.70199(8) 0.0165(4) Uani d . . . 1 . .
O O3A 0.77261(16) 0.73108(9) 0.70837(8) 0.0169(4) Uani d . . . 1 . .
O O4A 1.06571(18) 0.54064(9) 0.65193(9) 0.0193(4) Uani d . . . 1 . .
H H4A 1.070(4) 0.505(2) 0.6727(17) 0.042(10) Uiso d . . . 1 . .
F F1A 1.14016(17) 0.66470(10) 0.87138(8) 0.0374(4) Uani d . . . 1 . .
F F2A 0.9642(2) 0.61503(9) 0.91358(7) 0.0379(4) Uani d . . . 1 . .
F F3A 1.0151(2) 0.59843(8) 0.81399(8) 0.0370(4) Uani d . . . 1 . .
C C1A 0.9661(2) 0.74212(11) 0.78140(11) 0.0140(5) Uani d . . . 1 . .
H H1A 1.0691 0.7383 0.7767 0.017 Uiso calc U . R 1 . .
C C2A 0.9166(3) 0.70351(13) 0.84223(11) 0.0178(5) Uani d . . . 1 . .
H H2A 0.8208 0.6857 0.8348 0.021 Uiso calc U . R 1 . .
C C3A 0.9118(3) 0.75829(14) 0.89462(12) 0.0234(6) Uani d . . . 1 . .
H H301 0.8448 0.7461 0.9287 0.028 Uiso calc U . R 1 . .
H H302 1.0045 0.765 0.9141 0.028 Uiso calc U . R 1 . .
C C4A 0.8651(3) 0.82133(14) 0.85891(12) 0.0207(6) Uani d . . . 1 . .
H H401 0.7626 0.8238 0.8563 0.025 Uiso calc U . R 1 . .
H H402 0.9006 0.8628 0.8797 0.025 Uiso calc U . R 1 . .
C C5A 1.0104(3) 0.64636(14) 0.86011(12) 0.0262(6) Uani d . . . 1 . .
C C6A 0.9571(2) 0.86518(13) 0.75724(11) 0.0151(5) Uani d . . . 1 . .
C C7A 1.0305(3) 0.89041(13) 0.64688(11) 0.0181(5) Uani d . . . 1 . .
C C8A 1.1371(3) 0.94401(15) 0.66300(14) 0.0290(6) Uani d . . . 1 . .
H H801 1.1085 0.968 0.7019 0.043 Uiso calc U . R 1 . .
H H802 1.1442 0.9761 0.6274 0.043 Uiso calc U . R 1 . .
H H803 1.2275 0.9226 0.6701 0.043 Uiso calc U . R 1 . .
C C9A 0.8916(3) 0.92063(16) 0.62850(13) 0.0269(6) Uani d . . . 1 . .
H H901 0.822 0.8846 0.6256 0.04 Uiso calc U . R 1 . .
H H902 0.8999 0.9433 0.5869 0.04 Uiso calc U . R 1 . .
H H903 0.8631 0.9535 0.6611 0.04 Uiso calc U . R 1 . .
C C10A 1.0827(3) 0.84338(15) 0.59493(12) 0.0274(6) Uani d . . . 1 . .
H H10A 1.1683 0.8213 0.6093 0.041 Uiso calc U . R 1 . .
H H10B 1.1016 0.8694 0.5559 0.041 Uiso calc U . R 1 . .
H H10C 1.0121 0.809 0.5859 0.041 Uiso calc U . R 1 . .
C C11A 0.8935(2) 0.71469(12) 0.72161(11) 0.0126(5) Uani d . . . 1 . .
C C12A 0.9130(2) 0.63466(12) 0.63188(11) 0.0146(5) Uani d . . . 1 . .
H H12A 0.8119 0.6458 0.6285 0.018 Uiso calc U . R 1 . .
C C13A 0.9246(2) 0.55867(12) 0.64260(12) 0.0165(5) Uani d . . . 1 . .
H H13A 0.8695 0.5455 0.6807 0.02 Uiso calc U . R 1 . .
H H13B 0.8869 0.5343 0.605 0.02 Uiso calc U . R 1 . .
C C14A 0.9821(2) 0.65820(12) 0.57017(11) 0.0147(5) Uani d . . . 1 . .
C C15A 0.9020(3) 0.67355(14) 0.51721(12) 0.0197(5) Uani d . . . 1 . .
H H15A 0.804 0.6685 0.5194 0.024 Uiso calc U . R 1 . .
C C16A 0.9630(3) 0.69629(15) 0.46080(12) 0.0248(6) Uani d . . . 1 . .
H H16A 0.9065 0.7076 0.4251 0.03 Uiso calc U . R 1 . .
C C17A 1.1065(3) 0.70244(13) 0.45655(12) 0.0208(5) Uani d . . . 1 . .
H H17A 1.1485 0.7178 0.418 0.025 Uiso calc U . R 1 . .
C C18A 1.1876(3) 0.68605(13) 0.50900(12) 0.0198(5) Uani d . . . 1 . .
H H18A 1.2859 0.6891 0.5061 0.024 Uiso calc U . R 1 . .
C C19A 1.1263(2) 0.66513(12) 0.56583(11) 0.0157(5) Uani d . . . 1 . .
H H19A 1.1827 0.6555 0.602 0.019 Uiso calc U . R 1 . .
N N1B 0.4412(2) 0.56457(10) 0.77118(9) 0.0154(4) Uani d . . . 1 . .
N N2B 0.4682(2) 0.72852(10) 0.73063(9) 0.0144(4) Uani d . . . 1 . .
H H2D 0.559(3) 0.7239(13) 0.7339(12) 0.008(6) Uiso d . . . 1 . .
O O1B 0.58679(17) 0.62307(9) 0.83630(8) 0.0191(4) Uani d . . . 1 . .
O O2B 0.44117(18) 0.54081(9) 0.87475(8) 0.0208(4) Uani d . . . 1 . .
O O3B 0.26239(16) 0.67557(9) 0.72049(9) 0.0206(4) Uani d . . . 1 . .
O O4B 0.63658(17) 0.84936(10) 0.74624(9) 0.0196(4) Uani d . . . 1 . .
H H4B 0.687(4) 0.8143(18) 0.7347(15) 0.035(9) Uiso d . . . 1 . .
F F1B 0.43585(16) 0.53272(9) 0.55164(7) 0.0307(4) Uani d . . . 1 . .
F F2B 0.51388(18) 0.63059(8) 0.58006(7) 0.0305(4) Uani d . . . 1 . .
F F3B 0.62168(15) 0.54012(9) 0.60840(7) 0.0274(4) Uani d . . . 1 . .
C C1B 0.4683(2) 0.60675(12) 0.71516(10) 0.0132(5) Uani d . . . 1 . .
H H1B 0.5701 0.6145 0.7092 0.016 Uiso calc U . R 1 . .
C C2B 0.4072(2) 0.56407(12) 0.65943(11) 0.0134(5) Uani d . . . 1 . .
H H2B 0.3138 0.583 0.6486 0.016 Uiso calc U . R 1 . .
C C3B 0.3857(3) 0.49294(12) 0.68754(12) 0.0162(5) Uani d . . . 1 . .
H H311 0.3106 0.4683 0.665 0.019 Uiso calc U . R 1 . .
H H312 0.4721 0.4659 0.6858 0.019 Uiso calc U . R 1 . .
C C4B 0.3453(2) 0.50951(12) 0.75636(11) 0.0154(5) Uani d . . . 1 . .
H H411 0.2474 0.5245 0.7593 0.018 Uiso calc U . R 1 . .
H H412 0.3598 0.4703 0.7851 0.018 Uiso calc U . R 1 . .
C C5B 0.4941(3) 0.56636(13) 0.60045(12) 0.0191(5) Uani d . . . 1 . .
C C6B 0.4982(2) 0.58008(12) 0.82901(11) 0.0154(5) Uani d . . . 1 . .
C C7B 0.4815(3) 0.54841(13) 0.94298(11) 0.0193(5) Uani d . . . 1 . .
C C8B 0.3798(3) 0.50173(15) 0.97676(13) 0.0273(6) Uani d . . . 1 . .
H H811 0.2849 0.5181 0.9699 0.041 Uiso calc U . R 1 . .
H H812 0.4001 0.5011 1.0228 0.041 Uiso calc U . R 1 . .
H H813 0.3887 0.4559 0.9594 0.041 Uiso calc U . R 1 . .
C C9B 0.6294(3) 0.52385(14) 0.95146(13) 0.0234(6) Uani d . . . 1 . .
H H911 0.6365 0.4769 0.9369 0.035 Uiso calc U . R 1 . .
H H912 0.6552 0.5265 0.9968 0.035 Uiso calc U . R 1 . .
H H913 0.6922 0.5523 0.9262 0.035 Uiso calc U . R 1 . .
C C10B 0.4623(3) 0.62070(14) 0.96466(12) 0.0261(6) Uani d . . . 1 . .
H H10D 0.5346 0.6491 0.9455 0.039 Uiso calc U . R 1 . .
H H10E 0.4692 0.623 1.0115 0.039 Uiso calc U . R 1 . .
H H10F 0.3708 0.6369 0.9511 0.039 Uiso calc U . R 1 . .
C C11B 0.3897(2) 0.67398(12) 0.72197(10) 0.0135(5) Uani d . . . 1 . .
C C12B 0.4083(2) 0.79548(12) 0.74072(11) 0.0149(5) Uani d . . . 1 . .
H H12B 0.32 0.798 0.7156 0.018 Uiso calc U . R 1 . .
C C13B 0.5077(2) 0.84856(12) 0.71380(11) 0.0165(5) Uani d . . . 1 . .
H H13C 0.524 0.8392 0.6678 0.02 Uiso calc U . R 1 . .
H H13D 0.4641 0.8937 0.7173 0.02 Uiso calc U . R 1 . .
C C14B 0.3738(2) 0.81028(12) 0.81069(12) 0.0161(5) Uani d . . . 1 . .
C C15B 0.4426(3) 0.77888(14) 0.86084(12) 0.0246(6) Uani d . . . 1 . .
H H15B 0.5089 0.7445 0.8524 0.03 Uiso calc U . R 1 . .
C C16B 0.4141(4) 0.79801(15) 0.92366(13) 0.0332(7) Uani d . . . 1 . .
H H16B 0.4625 0.777 0.958 0.04 Uiso calc U . R 1 . .
C C17B 0.3160(3) 0.84737(15) 0.93672(13) 0.0293(6) Uani d . . . 1 . .
H H17B 0.297 0.86 0.9798 0.035 Uiso calc U . R 1 . .
C C18B 0.2457(3) 0.87806(14) 0.88678(13) 0.0251(6) Uani d . . . 1 . .
H H18B 0.1772 0.9114 0.8954 0.03 Uiso calc U . R 1 . .
C C19B 0.2759(3) 0.85997(13) 0.82394(12) 0.0199(5) Uani d . . . 1 . .
H H19B 0.2291 0.8818 0.7897 0.024 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
N1A C6A . 1.354(3) ?
N1A C1A . 1.460(3) ?
N1A C4A . 1.463(3) ?
N2A C11A . 1.328(3) ?
N2A C12A . 1.465(3) ?
N2A H2C . 0.85(3) ?
O1A C6A . 1.221(3) ?
O2A C6A . 1.345(3) ?
O2A C7A . 1.488(3) ?
O3A C11A . 1.240(3) ?
O4A C13A . 1.419(3) ?
O4A H4A . 0.83(4) ?
F1A C5A . 1.322(3) ?
F2A C5A . 1.352(3) ?
F3A C5A . 1.352(3) ?
C1A C11A . 1.530(3) ?
C1A C2A . 1.556(3) ?
C1A H1A . 1.0 ?
C2A C5A . 1.494(4) ?
C2A C3A . 1.540(3) ?
C2A H2A . 1.0 ?
C3A C4A . 1.521(4) ?
C3A H301 . 0.99 ?
C3A H302 . 0.99 ?
C4A H401 . 0.99 ?
C4A H402 . 0.99 ?
C7A C8A . 1.514(4) ?
C7A C9A . 1.515(4) ?
C7A C10A . 1.515(3) ?
C8A H801 . 0.98 ?
C8A H802 . 0.98 ?
C8A H803 . 0.98 ?
C9A H901 . 0.98 ?
C9A H902 . 0.98 ?
C9A H903 . 0.98 ?
C10A H10A . 0.98 ?
C10A H10B . 0.98 ?
C10A H10C . 0.98 ?
C12A C14A . 1.523(3) ?
C12A C13A . 1.524(3) ?
C12A H12A . 1.0 ?
C13A H13A . 0.99 ?
C13A H13B . 0.99 ?
C14A C15A . 1.382(3) ?
C14A C19A . 1.399(3) ?
C15A C16A . 1.391(4) ?
C15A H15A . 0.95 ?
C16A C17A . 1.390(4) ?
C16A H16A . 0.95 ?
C17A C18A . 1.383(4) ?
C17A H17A . 0.95 ?
C18A C19A . 1.388(4) ?
C18A H18A . 0.95 ?
C19A H19A . 0.95 ?
N1B C6B . 1.361(3) ?
N1B C1B . 1.460(3) ?
N1B C4B . 1.461(3) ?
N2B C11B . 1.330(3) ?
N2B C12B . 1.460(3) ?
N2B H2D . 0.88(3) ?
O1B C6B . 1.214(3) ?
O2B C6B . 1.347(3) ?
O2B C7B . 1.484(3) ?
O3B C11B . 1.227(3) ?
O4B C13B . 1.414(3) ?
O4B H4B . 0.88(4) ?
F1B C5B . 1.340(3) ?
F2B C5B . 1.353(3) ?
F3B C5B . 1.344(3) ?
C1B C11B . 1.537(3) ?
C1B C2B . 1.553(3) ?
C1B H1B . 1.0 ?
C2B C5B . 1.489(3) ?
C2B C3B . 1.538(3) ?
C2B H2B . 1.0 ?
C3B C4B . 1.524(3) ?
C3B H311 . 0.99 ?
C3B H312 . 0.99 ?
C4B H411 . 0.99 ?
C4B H412 . 0.99 ?
C7B C10B . 1.511(4) ?
C7B C9B . 1.515(4) ?
C7B C8B . 1.520(4) ?
C8B H811 . 0.98 ?
C8B H812 . 0.98 ?
C8B H813 . 0.98 ?
C9B H911 . 0.98 ?
C9B H912 . 0.98 ?
C9B H913 . 0.98 ?
C10B H10D . 0.98 ?
C10B H10E . 0.98 ?
C10B H10F . 0.98 ?
C12B C14B . 1.526(3) ?
C12B C13B . 1.528(3) ?
C12B H12B . 1.0 ?
C13B H13C . 0.99 ?
C13B H13D . 0.99 ?
C14B C15B . 1.386(4) ?
C14B C19B . 1.389(4) ?
C15B C16B . 1.392(4) ?
C15B H15B . 0.95 ?
C16B C17B . 1.386(4) ?
C16B H16B . 0.95 ?
C17B C18B . 1.383(4) ?
C17B H17B . 0.95 ?
C18B C19B . 1.390(4) ?
C18B H18B . 0.95 ?
C19B H19B . 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
C6A N1A C1A . . 124.16(19) ?
C6A N1A C4A . . 121.4(2) ?
C1A N1A C4A . . 114.06(19) ?
C11A N2A C12A . . 123.3(2) ?
C11A N2A H2C . . 118.(2) ?
C12A N2A H2C . . 119.(2) ?
C6A O2A C7A . . 120.48(19) ?
C13A O4A H4A . . 109.(3) ?
N1A C1A C11A . . 112.43(19) ?
N1A C1A C2A . . 102.72(18) ?
C11A C1A C2A . . 110.58(19) ?
N1A C1A H1A . . 110.3 ?
C11A C1A H1A . . 110.3 ?
C2A C1A H1A . . 110.3 ?
C5A C2A C3A . . 111.9(2) ?
C5A C2A C1A . . 112.9(2) ?
C3A C2A C1A . . 104.1(2) ?
C5A C2A H2A . . 109.3 ?
C3A C2A H2A . . 109.3 ?
C1A C2A H2A . . 109.3 ?
C4A C3A C2A . . 103.7(2) ?
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 ?
N1A C4A C3A . . 102.6(2) ?
N1A C4A H401 . . 111.2 ?
C3A C4A H401 . . 111.2 ?
N1A C4A H402 . . 111.2 ?
C3A C4A H402 . . 111.2 ?
H401 C4A H402 . . 109.2 ?
F1A C5A F3A . . 106.7(2) ?
F1A C5A F2A . . 106.9(2) ?
F3A C5A F2A . . 106.1(2) ?
F1A C5A C2A . . 114.1(2) ?
F3A C5A C2A . . 111.9(2) ?
F2A C5A C2A . . 110.7(2) ?
O1A C6A O2A . . 126.0(2) ?
O1A C6A N1A . . 123.9(2) ?
O2A C6A N1A . . 110.1(2) ?
O2A C7A C8A . . 109.9(2) ?
O2A C7A C9A . . 110.16(19) ?
C8A C7A C9A . . 112.3(2) ?
O2A C7A C10A . . 101.91(19) ?
C8A C7A C10A . . 111.3(2) ?
C9A C7A C10A . . 110.8(2) ?
C7A C8A H801 . . 109.5 ?
C7A C8A H802 . . 109.5 ?
H801 C8A H802 . . 109.5 ?
C7A C8A H803 . . 109.5 ?
H801 C8A H803 . . 109.5 ?
H802 C8A H803 . . 109.5 ?
C7A C9A H901 . . 109.5 ?
C7A C9A H902 . . 109.5 ?
H901 C9A H902 . . 109.5 ?
C7A C9A H903 . . 109.5 ?
H901 C9A H903 . . 109.5 ?
H902 C9A H903 . . 109.5 ?
C7A C10A H10A . . 109.5 ?
C7A C10A H10B . . 109.5 ?
H10A C10A H10B . . 109.5 ?
C7A C10A H10C . . 109.5 ?
H10A C10A H10C . . 109.5 ?
H10B C10A H10C . . 109.5 ?
O3A C11A N2A . . 123.9(2) ?
O3A C11A C1A . . 121.2(2) ?
N2A C11A C1A . . 114.87(19) ?
N2A C12A C14A . . 111.47(19) ?
N2A C12A C13A . . 109.79(19) ?
C14A C12A C13A . . 113.18(19) ?
N2A C12A H12A . . 107.4 ?
C14A C12A H12A . . 107.4 ?
C13A C12A H12A . . 107.4 ?
O4A C13A C12A . . 109.77(19) ?
O4A C13A H13A . . 109.7 ?
C12A C13A H13A . . 109.7 ?
O4A C13A H13B . . 109.7 ?
C12A C13A H13B . . 109.7 ?
H13A C13A H13B . . 108.2 ?
C15A C14A C19A . . 118.8(2) ?
C15A C14A C12A . . 120.0(2) ?
C19A C14A C12A . . 121.3(2) ?
C14A C15A C16A . . 120.8(2) ?
C14A C15A H15A . . 119.6 ?
C16A C15A H15A . . 119.6 ?
C17A C16A C15A . . 120.2(2) ?
C17A C16A H16A . . 119.9 ?
C15A C16A H16A . . 119.9 ?
C18A C17A C16A . . 119.4(2) ?
C18A C17A H17A . . 120.3 ?
C16A C17A H17A . . 120.3 ?
C17A C18A C19A . . 120.4(2) ?
C17A C18A H18A . . 119.8 ?
C19A C18A H18A . . 119.8 ?
C18A C19A C14A . . 120.5(2) ?
C18A C19A H19A . . 119.8 ?
C14A C19A H19A . . 119.8 ?
C6B N1B C1B . . 120.63(19) ?
C6B N1B C4B . . 127.6(2) ?
C1B N1B C4B . . 111.68(18) ?
C11B N2B C12B . . 122.04(19) ?
C11B N2B H2D . . 119.3(18) ?
C12B N2B H2D . . 118.4(18) ?
C6B O2B C7B . . 120.99(19) ?
C13B O4B H4B . . 110.(2) ?
N1B C1B C11B . . 109.41(18) ?
N1B C1B C2B . . 102.79(18) ?
C11B C1B C2B . . 110.64(18) ?
N1B C1B H1B . . 111.2 ?
C11B C1B H1B . . 111.2 ?
C2B C1B H1B . . 111.2 ?
C5B C2B C3B . . 114.7(2) ?
C5B C2B C1B . . 112.90(19) ?
C3B C2B C1B . . 105.22(18) ?
C5B C2B H2B . . 107.9 ?
C3B C2B H2B . . 107.9 ?
C1B C2B H2B . . 107.9 ?
C4B C3B C2B . . 101.37(19) ?
C4B C3B H311 . . 111.5 ?
C2B C3B H311 . . 111.5 ?
C4B C3B H312 . . 111.5 ?
C2B C3B H312 . . 111.5 ?
H311 C3B H312 . . 109.3 ?
N1B C4B C3B . . 101.42(18) ?
N1B C4B H411 . . 111.5 ?
C3B C4B H411 . . 111.5 ?
N1B C4B H412 . . 111.5 ?
C3B C4B H412 . . 111.5 ?
H411 C4B H412 . . 109.3 ?
F1B C5B F3B . . 106.6(2) ?
F1B C5B F2B . . 106.6(2) ?
F3B C5B F2B . . 105.8(2) ?
F1B C5B C2B . . 112.2(2) ?
F3B C5B C2B . . 113.6(2) ?
F2B C5B C2B . . 111.6(2) ?
O1B C6B O2B . . 126.9(2) ?
O1B C6B N1B . . 123.5(2) ?
O2B C6B N1B . . 109.5(2) ?
O2B C7B C10B . . 110.6(2) ?
O2B C7B C9B . . 109.0(2) ?
C10B C7B C9B . . 112.6(2) ?
O2B C7B C8B . . 102.4(2) ?
C10B C7B C8B . . 110.9(2) ?
C9B C7B C8B . . 110.9(2) ?
C7B C8B H811 . . 109.5 ?
C7B C8B H812 . . 109.5 ?
H811 C8B H812 . . 109.5 ?
C7B C8B H813 . . 109.5 ?
H811 C8B H813 . . 109.5 ?
H812 C8B H813 . . 109.5 ?
C7B C9B H911 . . 109.5 ?
C7B C9B H912 . . 109.5 ?
H911 C9B H912 . . 109.5 ?
C7B C9B H913 . . 109.5 ?
H911 C9B H913 . . 109.5 ?
H912 C9B H913 . . 109.5 ?
C7B C10B H10D . . 109.5 ?
C7B C10B H10E . . 109.5 ?
H10D C10B H10E . . 109.5 ?
C7B C10B H10F . . 109.5 ?
H10D C10B H10F . . 109.5 ?
H10E C10B H10F . . 109.5 ?
O3B C11B N2B . . 123.4(2) ?
O3B C11B C1B . . 120.8(2) ?
N2B C11B C1B . . 115.73(19) ?
N2B C12B C14B . . 113.5(2) ?
N2B C12B C13B . . 108.80(19) ?
C14B C12B C13B . . 110.9(2) ?
N2B C12B H12B . . 107.8 ?
C14B C12B H12B . . 107.8 ?
C13B C12B H12B . . 107.8 ?
O4B C13B C12B . . 112.45(19) ?
O4B C13B H13C . . 109.1 ?
C12B C13B H13C . . 109.1 ?
O4B C13B H13D . . 109.1 ?
C12B C13B H13D . . 109.1 ?
H13C C13B H13D . . 107.8 ?
C15B C14B C19B . . 119.4(2) ?
C15B C14B C12B . . 122.2(2) ?
C19B C14B C12B . . 118.3(2) ?
C14B C15B C16B . . 119.7(3) ?
C14B C15B H15B . . 120.2 ?
C16B C15B H15B . . 120.2 ?
C17B C16B C15B . . 120.7(3) ?
C17B C16B H16B . . 119.6 ?
C15B C16B H16B . . 119.6 ?
C18B C17B C16B . . 119.6(3) ?
C18B C17B H17B . . 120.2 ?
C16B C17B H17B . . 120.2 ?
C17B C18B C19B . . 119.7(2) ?
C17B C18B H18B . . 120.1 ?
C19B C18B H18B . . 120.1 ?
C14B C19B C18B . . 120.8(2) ?
C14B C19B H19B . . 119.6 ?
C18B C19B H19B . . 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
C6A N1A C1A C11A . . . . -65.2(3) ?
C4A N1A C1A C11A . . . . 121.5(2) ?
C6A N1A C1A C2A . . . . 176.0(2) ?
C4A N1A C1A C2A . . . . 2.7(2) ?
N1A C1A C2A C5A . . . . -144.9(2) ?
C11A C1A C2A C5A . . . . 95.0(2) ?
N1A C1A C2A C3A . . . . -23.3(2) ?
C11A C1A C2A C3A . . . . -143.5(2) ?
C5A C2A C3A C4A . . . . 157.5(2) ?
C1A C2A C3A C4A . . . . 35.3(3) ?
C6A N1A C4A C3A . . . . -154.3(2) ?
C1A N1A C4A C3A . . . . 19.2(3) ?
C2A C3A C4A N1A . . . . -32.9(2) ?
C3A C2A C5A F1A . . . . -58.4(3) ?
C1A C2A C5A F1A . . . . 58.6(3) ?
C3A C2A C5A F3A . . . . -179.7(2) ?
C1A C2A C5A F3A . . . . -62.7(3) ?
C3A C2A C5A F2A . . . . 62.2(3) ?
C1A C2A C5A F2A . . . . 179.2(2) ?
C7A O2A C6A O1A . . . . -12.1(3) ?
C7A O2A C6A N1A . . . . 168.08(19) ?
C1A N1A C6A O1A . . . . -172.9(2) ?
C4A N1A C6A O1A . . . . -0.1(4) ?
C1A N1A C6A O2A . . . . 6.9(3) ?
C4A N1A C6A O2A . . . . 179.67(19) ?
C6A O2A C7A C8A . . . . 67.2(3) ?
C6A O2A C7A C9A . . . . -57.0(3) ?
C6A O2A C7A C10A . . . . -174.6(2) ?
C12A N2A C11A O3A . . . . -2.4(4) ?
C12A N2A C11A C1A . . . . 174.9(2) ?
N1A C1A C11A O3A . . . . -35.7(3) ?
C2A C1A C11A O3A . . . . 78.5(3) ?
N1A C1A C11A N2A . . . . 147.0(2) ?
C2A C1A C11A N2A . . . . -98.9(2) ?
C11A N2A C12A C14A . . . . 111.5(2) ?
C11A N2A C12A C13A . . . . -122.3(2) ?
N2A C12A C13A O4A . . . . -59.8(3) ?
C14A C12A C13A O4A . . . . 65.5(3) ?
N2A C12A C14A C15A . . . . -132.7(2) ?
C13A C12A C14A C15A . . . . 102.9(3) ?
N2A C12A C14A C19A . . . . 46.9(3) ?
C13A C12A C14A C19A . . . . -77.4(3) ?
C19A C14A C15A C16A . . . . -0.8(4) ?
C12A C14A C15A C16A . . . . 178.8(2) ?
C14A C15A C16A C17A . . . . 1.4(4) ?
C15A C16A C17A C18A . . . . -0.3(4) ?
C16A C17A C18A C19A . . . . -1.5(4) ?
C17A C18A C19A C14A . . . . 2.1(4) ?
C15A C14A C19A C18A . . . . -1.0(4) ?
C12A C14A C19A C18A . . . . 179.4(2) ?
C6B N1B C1B C11B . . . . -72.2(3) ?
C4B N1B C1B C11B . . . . 105.2(2) ?
C6B N1B C1B C2B . . . . 170.2(2) ?
C4B N1B C1B C2B . . . . -12.4(2) ?
N1B C1B C2B C5B . . . . -140.5(2) ?
C11B C1B C2B C5B . . . . 102.7(2) ?
N1B C1B C2B C3B . . . . -14.7(2) ?
C11B C1B C2B C3B . . . . -131.41(19) ?
C5B C2B C3B C4B . . . . 159.44(19) ?
C1B C2B C3B C4B . . . . 34.7(2) ?
C6B N1B C4B C3B . . . . -148.3(2) ?
C1B N1B C4B C3B . . . . 34.5(2) ?
C2B C3B C4B N1B . . . . -41.0(2) ?
C3B C2B C5B F1B . . . . 63.2(3) ?
C1B C2B C5B F1B . . . . -176.2(2) ?
C3B C2B C5B F3B . . . . -57.7(3) ?
C1B C2B C5B F3B . . . . 62.9(3) ?
C3B C2B C5B F2B . . . . -177.2(2) ?
C1B C2B C5B F2B . . . . -56.6(3) ?
C7B O2B C6B O1B . . . . 1.8(4) ?
C7B O2B C6B N1B . . . . -178.3(2) ?
C1B N1B C6B O1B . . . . -9.8(4) ?
C4B N1B C6B O1B . . . . 173.2(2) ?
C1B N1B C6B O2B . . . . 170.3(2) ?
C4B N1B C6B O2B . . . . -6.7(3) ?
C6B O2B C7B C10B . . . . 54.7(3) ?
C6B O2B C7B C9B . . . . -69.6(3) ?
C6B O2B C7B C8B . . . . 172.9(2) ?
C12B N2B C11B O3B . . . . 1.5(4) ?
C12B N2B C11B C1B . . . . -177.22(19) ?
N1B C1B C11B O3B . . . . -67.2(3) ?
C2B C1B C11B O3B . . . . 45.4(3) ?
N1B C1B C11B N2B . . . . 111.6(2) ?
C2B C1B C11B N2B . . . . -135.9(2) ?
C11B N2B C12B C14B . . . . 86.4(3) ?
C11B N2B C12B C13B . . . . -149.7(2) ?
N2B C12B C13B O4B . . . . -63.4(2) ?
C14B C12B C13B O4B . . . . 62.0(2) ?
N2B C12B C14B C15B . . . . 25.8(3) ?
C13B C12B C14B C15B . . . . -97.0(3) ?
N2B C12B C14B C19B . . . . -158.2(2) ?
C13B C12B C14B C19B . . . . 79.0(3) ?
C19B C14B C15B C16B . . . . -0.7(4) ?
C12B C14B C15B C16B . . . . 175.2(3) ?
C14B C15B C16B C17B . . . . 1.1(5) ?
C15B C16B C17B C18B . . . . -0.1(5) ?
C16B C17B C18B C19B . . . . -1.1(5) ?
C15B C14B C19B C18B . . . . -0.5(4) ?
C12B C14B C19B C18B . . . . -176.6(2) ?
C17B C18B C19B C14B . . . . 1.4(4) ?

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 H2C O3B 1_655 0.85(3) 2.09(3) 2.921(3) 166.(3) ?
O4A H4A O1A 3_746 0.83(4) 1.97(4) 2.801(2) 174.(4) ?
N2B H2D O3A . 0.88(3) 2.13(3) 2.969(3) 159.(2) ?
O4B H4B N1A . 0.88(4) 2.63(3) 3.070(3) 112.(2) ?
O4B H4B O3A . 0.88(4) 1.92(4) 2.795(3) 172.(3) ?


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

data_dan9437_2S3S-5b
_database_code_depnum_ccdc_archive 'CCDC 2193974'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-08-01 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 F5 N2 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         452.42
_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                   9.8654(2)
_cell_length_b                   19.9514(4)
_cell_length_c                   21.5323(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4238.17(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9794
_cell_measurement_theta_min      3.0196
_cell_measurement_theta_max      68.2958
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.253
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.060
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1888

_exptl_absorpt_coefficient_mu    1.107
_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  0.86
_exptl_absorpt_correction_T_max  0.94

_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            41676
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         68.29
_diffrn_reflns_theta_full        68.29
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_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.

The hydrogen atoms at N2A, N2B, O4A and O4B were refined
freely
;

_reflns_number_total             7734
_reflns_number_gt                7320
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0272
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0633
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_number_reflns         7734
_refine_ls_number_parameters     581
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0281P)²+0.8862P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 3072 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)

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
N N1A 0.4296(2) 0.57042(8) 0.78068(8) 0.0146(4) Uani d . . . 1 . .
N N2A 0.4768(2) 0.72928(8) 0.73050(9) 0.0142(4) Uani d . . . 1 . .
H H2C 0.557(3) 0.7232(12) 0.7353(11) 0.012(6) Uiso d . . . 1 . .
O O1A 0.57855(17) 0.62544(7) 0.84246(7) 0.0181(3) Uani d . . . 1 . .
O O2A 0.43476(17) 0.54519(7) 0.88092(6) 0.0183(3) Uani d . . . 1 . .
O O3A 0.27298(16) 0.67967(7) 0.71782(7) 0.0177(3) Uani d . . . 1 . .
O O4A 0.64572(16) 0.84865(7) 0.74533(8) 0.0187(3) Uani d . . . 1 . .
H H4A 0.691(3) 0.8131(17) 0.7345(15) 0.039(9) Uiso d . . . 1 . .
F F1A 0.64028(13) 0.53172(7) 0.63994(6) 0.0202(3) Uani d . . . 1 . .
F F2A 0.55632(15) 0.62428(6) 0.60230(6) 0.0213(3) Uani d . . . 1 . .
F F3A 0.44893(16) 0.46068(6) 0.57134(6) 0.0264(3) Uani d . . . 1 . .
F F4A 0.37543(15) 0.55483(7) 0.53528(6) 0.0275(3) Uani d . . . 1 . .
F F5A 0.58196(16) 0.52464(7) 0.51915(6) 0.0284(3) Uani d . . . 1 . .
C C1A 0.4694(2) 0.60787(10) 0.72507(9) 0.0120(4) Uani d . . . 1 . .
H H1A 0.57 0.6138 0.7232 0.014 Uiso calc U . R 1 . .
C C2A 0.4185(2) 0.56256(10) 0.67108(9) 0.0114(4) Uani d . . . 1 . .
H H2A 0.333 0.5822 0.654 0.014 Uiso calc U . R 1 . .
C C3A 0.3852(2) 0.49464(10) 0.70111(10) 0.0140(4) Uani d . . . 1 . .
H H301 0.3124 0.4712 0.6781 0.017 Uiso calc U . R 1 . .
H H302 0.4662 0.4655 0.703 0.017 Uiso calc U . R 1 . .
C C4A 0.3383(2) 0.51471(10) 0.76598(10) 0.0140(4) Uani d . . . 1 . .
H H401 0.2424 0.5294 0.7658 0.017 Uiso calc U . R 1 . .
H H402 0.3493 0.4774 0.7958 0.017 Uiso calc U . R 1 . .
C C5A 0.5228(2) 0.56052(10) 0.62033(10) 0.0145(4) Uani d . . . 1 . .
C C6A 0.4816(2) 0.52407(11) 0.56061(10) 0.0176(5) Uani d . . . 1 . .
C C7A 0.4891(2) 0.58390(10) 0.83589(10) 0.0140(4) Uani d . . . 1 . .
C C8A 0.4862(2) 0.54829(11) 0.94542(10) 0.0162(5) Uani d . . . 1 . .
C C9A 0.3906(3) 0.50115(13) 0.97944(11) 0.0248(5) Uani d . . . 1 . .
H H901 0.2977 0.5183 0.9766 0.037 Uiso calc U . R 1 . .
H H902 0.4173 0.4982 1.0232 0.037 Uiso calc U . R 1 . .
H H903 0.395 0.4566 0.9605 0.037 Uiso calc U . R 1 . .
C C10A 0.6297(3) 0.52195(12) 0.94712(12) 0.0249(5) Uani d . . . 1 . .
H H10A 0.6312 0.4758 0.9314 0.037 Uiso calc U . R 1 . .
H H10B 0.6631 0.5227 0.99 0.037 Uiso calc U . R 1 . .
H H10C 0.6877 0.5502 0.9211 0.037 Uiso calc U . R 1 . .
C C11A 0.4741(3) 0.61924(12) 0.97054(11) 0.0266(6) Uani d . . . 1 . .
H H11A 0.5389 0.6484 0.9491 0.04 Uiso calc U . R 1 . .
H H11B 0.4936 0.6192 1.0152 0.04 Uiso calc U . R 1 . .
H H11C 0.3818 0.6358 0.9635 0.04 Uiso calc U . R 1 . .
C C12A 0.3967(2) 0.67569(10) 0.72391(9) 0.0114(4) Uani d . . . 1 . .
C C13A 0.4213(2) 0.79679(10) 0.73531(10) 0.0147(4) Uani d . . . 1 . .
H H13A 0.3392 0.7989 0.7081 0.018 Uiso calc U . R 1 . .
C C14A 0.5251(2) 0.84653(10) 0.70955(10) 0.0162(5) Uani d . . . 1 . .
H H14A 0.5479 0.8338 0.6664 0.019 Uiso calc U . R 1 . .
H H14B 0.4841 0.8918 0.7086 0.019 Uiso calc U . R 1 . .
C C15A 0.3770(2) 0.81406(10) 0.80116(10) 0.0146(4) Uani d . . . 1 . .
C C16A 0.4284(3) 0.78106(11) 0.85284(11) 0.0200(5) Uani d . . . 1 . .
H H16A 0.4926 0.746 0.8476 0.024 Uiso calc U . R 1 . .
C C17A 0.3867(3) 0.79901(12) 0.91215(11) 0.0254(6) Uani d . . . 1 . .
H H17A 0.4227 0.7763 0.9472 0.031 Uiso calc U . R 1 . .
C C18A 0.2929(3) 0.84986(12) 0.92049(12) 0.0239(5) Uani d . . . 1 . .
H H18A 0.2643 0.8619 0.9611 0.029 Uiso calc U . R 1 . .
C C19A 0.2411(2) 0.88305(11) 0.86921(12) 0.0228(5) Uani d . . . 1 . .
H H19A 0.1768 0.918 0.8747 0.027 Uiso calc U . R 1 . .
C C20A 0.2828(2) 0.86536(11) 0.80989(11) 0.0182(5) Uani d . . . 1 . .
H H20A 0.2469 0.8884 0.7749 0.022 Uiso calc U . R 1 . .
N N1B 0.9374(2) 0.81725(8) 0.79213(8) 0.0139(4) Uani d . . . 1 . .
N N2B 0.9798(2) 0.67438(9) 0.69121(8) 0.0126(4) Uani d . . D 1 . .
H H2D 1.060(2) 0.6675(12) 0.7007(12) 0.016(7) Uiso d . . D 1 . .
O O1B 0.93836(16) 0.92751(7) 0.76545(7) 0.0163(3) Uani d . . . 1 . .
O O2B 1.02121(16) 0.84591(7) 0.70097(7) 0.0152(3) Uani d . . . 1 . .
O O3B 0.78561(16) 0.73004(7) 0.71486(7) 0.0165(3) Uani d . . . 1 . .
O O4B 1.07686(16) 0.54352(7) 0.65799(7) 0.0181(3) Uani d . . . 1 . .
H H4B 1.081(3) 0.5068(16) 0.6802(15) 0.042(9) Uiso d . . . 1 . .
F F1B 1.17672(14) 0.67811(7) 0.85386(6) 0.0255(3) Uani d . . . 1 . .
F F2B 1.03412(16) 0.60606(6) 0.81460(6) 0.0277(3) Uani d . . . 1 . .
F F3B 1.07710(16) 0.66469(7) 0.96521(6) 0.0294(3) Uani d . . . 1 . .
F F4B 0.89988(16) 0.61222(8) 0.93260(7) 0.0332(4) Uani d . . . 1 . .
F F5B 1.09759(17) 0.56708(7) 0.92449(7) 0.0328(4) Uani d . . . 1 . .
C C1B 0.9818(2) 0.74818(9) 0.78006(9) 0.0127(4) Uani d . . . 1 . .
H H1B 1.0818 0.7468 0.7728 0.015 Uiso calc U . R 1 . .
C C2B 0.9453(2) 0.71194(10) 0.84188(9) 0.0159(5) Uani d . . . 1 . .
H H2B 0.8527 0.692 0.838 0.019 Uiso calc U . R 1 . .
C C3B 0.9412(3) 0.76857(11) 0.89042(10) 0.0194(5) Uani d . . . 1 . .
H H311 0.8828 0.7563 0.9261 0.023 Uiso calc U . R 1 . .
H H312 1.0333 0.7792 0.9058 0.023 Uiso calc U . R 1 . .
C C4B 0.8814(3) 0.82730(11) 0.85426(10) 0.0186(5) Uani d . . . 1 . .
H H411 0.7812 0.8254 0.8538 0.022 Uiso calc U . R 1 . .
H H412 0.9107 0.8707 0.872 0.022 Uiso calc U . R 1 . .
C C5B 1.0460(2) 0.65646(11) 0.85665(10) 0.0186(5) Uani d . . . 1 . .
C C6B 1.0298(3) 0.62443(11) 0.92100(11) 0.0219(5) Uani d . . . 1 . .
C C7B 0.9632(2) 0.86883(10) 0.75354(9) 0.0130(4) Uani d . . . 1 . .
C C8B 1.0262(2) 0.88829(10) 0.64444(10) 0.0164(5) Uani d . . . 1 . .
C C9B 0.8835(3) 0.90839(13) 0.62654(11) 0.0243(5) Uani d . . . 1 . .
H H911 0.8257 0.8685 0.6253 0.037 Uiso calc U . R 1 . .
H H912 0.8847 0.9296 0.5855 0.037 Uiso calc U . R 1 . .
H H913 0.8478 0.9401 0.6572 0.037 Uiso calc U . R 1 . .
C C10B 1.1180(3) 0.94837(12) 0.65459(12) 0.0276(6) Uani d . . . 1 . .
H H10D 1.0803 0.9767 0.6875 0.041 Uiso calc U . R 1 . .
H H10E 1.1244 0.9743 0.616 0.041 Uiso calc U . R 1 . .
H H10F 1.2085 0.9329 0.6667 0.041 Uiso calc U . R 1 . .
C C11B 1.0862(3) 0.84067(12) 0.59692(11) 0.0292(6) Uani d . . . 1 . .
H H11D 1.1754 0.8255 0.6111 0.044 Uiso calc U . R 1 . .
H H11E 1.0957 0.8638 0.557 0.044 Uiso calc U . R 1 . .
H H11F 1.0262 0.8019 0.5919 0.044 Uiso calc U . R 1 . .
C C12B 0.9059(2) 0.71710(10) 0.72482(9) 0.0113(4) Uani d . . . 1 . .
C C13B 0.9241(2) 0.63648(10) 0.63874(9) 0.0135(4) Uani d . . . 1 . .
H H13B 0.8251 0.6468 0.6363 0.016 Uiso calc U . R 1 . .
C C14B 0.9383(2) 0.56128(10) 0.65067(10) 0.0152(4) Uani d . . . 1 . .
H H14C 0.8874 0.5491 0.6887 0.018 Uiso calc U . R 1 . .
H H14D 0.899 0.5361 0.6154 0.018 Uiso calc U . R 1 . .
C C15B 0.9880(2) 0.65856(10) 0.57756(10) 0.0135(4) Uani d . . . 1 . .
C C16B 0.9057(2) 0.67217(11) 0.52671(10) 0.0194(5) Uani d . . . 1 . .
H H16B 0.8103 0.6668 0.53 0.023 Uiso calc U . R 1 . .
C C17B 0.9623(3) 0.69364(12) 0.47088(11) 0.0245(5) Uani d . . . 1 . .
H H17B 0.9052 0.7031 0.4365 0.029 Uiso calc U . R 1 . .
C C18B 1.1008(3) 0.70119(11) 0.46518(10) 0.0208(5) Uani d . . . 1 . .
H H18B 1.1389 0.7166 0.4272 0.025 Uiso calc U . R 1 . .
C C19B 1.1840(2) 0.68616(10) 0.51523(10) 0.0180(5) Uani d . . . 1 . .
H H19B 1.2796 0.6902 0.5112 0.022 Uiso calc U . R 1 . .
C C20B 1.1282(2) 0.66523(10) 0.57109(10) 0.0155(4) Uani d . . . 1 . .
H H20B 1.1858 0.6554 0.6052 0.019 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
N1A C7A . 1.353(3) ?
N1A C4A . 1.465(3) ?
N1A C1A . 1.465(3) ?
N2A C12A . 1.337(3) ?
N2A C13A . 1.458(3) ?
N2A H2C . 0.81(3) ?
O1A C7A . 1.219(3) ?
O2A C7A . 1.351(3) ?
O2A C8A . 1.480(3) ?
O3A C12A . 1.230(3) ?
O4A C14A . 1.419(3) ?
O4A H4A . 0.87(3) ?
F1A C5A . 1.361(3) ?
F2A C5A . 1.370(2) ?
F3A C6A . 1.325(3) ?
F4A C6A . 1.331(3) ?
F5A C6A . 1.333(3) ?
C1A C12A . 1.532(3) ?
C1A C2A . 1.556(3) ?
C1A H1A . 1.0 ?
C2A C5A . 1.502(3) ?
C2A C3A . 1.537(3) ?
C2A H2A . 1.0 ?
C3A C4A . 1.525(3) ?
C3A H301 . 0.99 ?
C3A H302 . 0.99 ?
C4A H401 . 0.99 ?
C4A H402 . 0.99 ?
C5A C6A . 1.532(3) ?
C8A C10A . 1.510(3) ?
C8A C11A . 1.520(3) ?
C8A C9A . 1.521(3) ?
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 . 1.523(3) ?
C13A C14A . 1.530(3) ?
C13A H13A . 1.0 ?
C14A H14A . 0.99 ?
C14A H14B . 0.99 ?
C15A C16A . 1.389(3) ?
C15A C20A . 1.395(3) ?
C16A C17A . 1.389(3) ?
C16A H16A . 0.95 ?
C17A C18A . 1.385(4) ?
C17A H17A . 0.95 ?
C18A C19A . 1.385(4) ?
C18A H18A . 0.95 ?
C19A C20A . 1.387(3) ?
C19A H19A . 0.95 ?
C20A H20A . 0.95 ?
N1B C7B . 1.347(3) ?
N1B C4B . 1.461(3) ?
N1B C1B . 1.469(2) ?
N2B C12B . 1.335(3) ?
N2B C13B . 1.466(3) ?
N2B H2D . 0.83(2) ?
O1B C7B . 1.223(2) ?
O2B C7B . 1.348(3) ?
O2B C8B . 1.483(2) ?
O3B C12B . 1.234(3) ?
O4B C14B . 1.421(3) ?
O4B H4B . 0.88(3) ?
F1B C5B . 1.361(3) ?
F2B C5B . 1.358(3) ?
F3B C6B . 1.330(3) ?
F4B C6B . 1.328(3) ?
F5B C6B . 1.328(3) ?
C1B C12B . 1.536(3) ?
C1B C2B . 1.557(3) ?
C1B H1B . 1.0 ?
C2B C5B . 1.521(3) ?
C2B C3B . 1.540(3) ?
C2B H2B . 1.0 ?
C3B C4B . 1.525(3) ?
C3B H311 . 0.99 ?
C3B H312 . 0.99 ?
C4B H411 . 0.99 ?
C4B H412 . 0.99 ?
C5B C6B . 1.534(3) ?
C8B C9B . 1.514(3) ?
C8B C11B . 1.516(3) ?
C8B C10B . 1.518(3) ?
C9B H911 . 0.98 ?
C9B H912 . 0.98 ?
C9B H913 . 0.98 ?
C10B H10D . 0.98 ?
C10B H10E . 0.98 ?
C10B H10F . 0.98 ?
C11B H11D . 0.98 ?
C11B H11E . 0.98 ?
C11B H11F . 0.98 ?
C13B C15B . 1.525(3) ?
C13B C14B . 1.528(3) ?
C13B H13B . 1.0 ?
C14B H14C . 0.99 ?
C14B H14D . 0.99 ?
C15B C16B . 1.390(3) ?
C15B C20B . 1.396(3) ?
C16B C17B . 1.393(3) ?
C16B H16B . 0.95 ?
C17B C18B . 1.380(4) ?
C17B H17B . 0.95 ?
C18B C19B . 1.388(3) ?
C18B H18B . 0.95 ?
C19B C20B . 1.387(3) ?
C19B H19B . 0.95 ?
C20B H20B . 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 N1A C4A . . 127.40(17) ?
C7A N1A C1A . . 120.01(17) ?
C4A N1A C1A . . 112.04(16) ?
C12A N2A C13A . . 121.6(2) ?
C12A N2A H2C . . 118.2(17) ?
C13A N2A H2C . . 119.9(17) ?
C7A O2A C8A . . 120.89(17) ?
C14A O4A H4A . . 105.(2) ?
N1A C1A C12A . . 109.77(16) ?
N1A C1A C2A . . 103.17(15) ?
C12A C1A C2A . . 110.49(17) ?
N1A C1A H1A . . 111.1 ?
C12A C1A H1A . . 111.1 ?
C2A C1A H1A . . 111.1 ?
C5A C2A C3A . . 115.40(17) ?
C5A C2A C1A . . 109.77(17) ?
C3A C2A C1A . . 105.48(16) ?
C5A C2A H2A . . 108.7 ?
C3A C2A H2A . . 108.7 ?
C1A C2A H2A . . 108.7 ?
C4A C3A C2A . . 102.64(15) ?
C4A C3A H301 . . 111.2 ?
C2A C3A H301 . . 111.2 ?
C4A C3A H302 . . 111.2 ?
C2A C3A H302 . . 111.2 ?
H301 C3A H302 . . 109.2 ?
N1A C4A C3A . . 102.18(17) ?
N1A C4A H401 . . 111.3 ?
C3A C4A H401 . . 111.3 ?
N1A C4A H402 . . 111.3 ?
C3A C4A H402 . . 111.3 ?
H401 C4A H402 . . 109.2 ?
F1A C5A F2A . . 105.94(17) ?
F1A C5A C2A . . 111.68(17) ?
F2A C5A C2A . . 110.27(16) ?
F1A C5A C6A . . 106.62(17) ?
F2A C5A C6A . . 105.47(16) ?
C2A C5A C6A . . 116.21(19) ?
F3A C6A F4A . . 108.67(19) ?
F3A C6A F5A . . 107.79(17) ?
F4A C6A F5A . . 107.83(18) ?
F3A C6A C5A . . 111.78(18) ?
F4A C6A C5A . . 109.50(17) ?
F5A C6A C5A . . 111.15(19) ?
O1A C7A O2A . . 126.38(19) ?
O1A C7A N1A . . 123.47(19) ?
O2A C7A N1A . . 110.15(18) ?
O2A C8A C10A . . 109.26(18) ?
O2A C8A C11A . . 110.22(18) ?
C10A C8A C11A . . 112.9(2) ?
O2A C8A C9A . . 102.31(17) ?
C10A C8A C9A . . 110.77(19) ?
C11A C8A C9A . . 110.8(2) ?
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 . . 123.1(2) ?
O3A C12A C1A . . 121.55(18) ?
N2A C12A C1A . . 115.35(19) ?
N2A C13A C15A . . 112.51(17) ?
N2A C13A C14A . . 108.81(18) ?
C15A C13A C14A . . 112.51(17) ?
N2A C13A H13A . . 107.6 ?
C15A C13A H13A . . 107.6 ?
C14A C13A H13A . . 107.6 ?
O4A C14A C13A . . 112.58(17) ?
O4A C14A H14A . . 109.1 ?
C13A C14A H14A . . 109.1 ?
O4A C14A H14B . . 109.1 ?
C13A C14A H14B . . 109.1 ?
H14A C14A H14B . . 107.8 ?
C16A C15A C20A . . 118.9(2) ?
C16A C15A C13A . . 122.25(19) ?
C20A C15A C13A . . 118.86(19) ?
C17A C16A C15A . . 120.4(2) ?
C17A C16A H16A . . 119.8 ?
C15A C16A H16A . . 119.8 ?
C18A C17A C16A . . 120.4(2) ?
C18A C17A H17A . . 119.8 ?
C16A C17A H17A . . 119.8 ?
C17A C18A C19A . . 119.6(2) ?
C17A C18A H18A . . 120.2 ?
C19A C18A H18A . . 120.2 ?
C18A C19A C20A . . 120.2(2) ?
C18A C19A H19A . . 119.9 ?
C20A C19A H19A . . 119.9 ?
C19A C20A C15A . . 120.5(2) ?
C19A C20A H20A . . 119.7 ?
C15A C20A H20A . . 119.7 ?
C7B N1B C4B . . 122.10(17) ?
C7B N1B C1B . . 123.45(17) ?
C4B N1B C1B . . 113.78(16) ?
C12B N2B C13B . . 122.87(19) ?
C12B N2B H2D . . 119.6(18) ?
C13B N2B H2D . . 117.5(17) ?
C7B O2B C8B . . 120.66(15) ?
C14B O4B H4B . . 108.(2) ?
N1B C1B C12B . . 111.75(17) ?
N1B C1B C2B . . 102.45(16) ?
C12B C1B C2B . . 111.24(17) ?
N1B C1B H1B . . 110.4 ?
C12B C1B H1B . . 110.4 ?
C2B C1B H1B . . 110.4 ?
C5B C2B C3B . . 114.18(19) ?
C5B C2B C1B . . 111.47(18) ?
C3B C2B C1B . . 104.23(16) ?
C5B C2B H2B . . 108.9 ?
C3B C2B H2B . . 108.9 ?
C1B C2B H2B . . 108.9 ?
C4B C3B C2B . . 103.15(17) ?
C4B C3B H311 . . 111.1 ?
C2B C3B H311 . . 111.1 ?
C4B C3B H312 . . 111.1 ?
C2B C3B H312 . . 111.1 ?
H311 C3B H312 . . 109.1 ?
N1B C4B C3B . . 102.47(17) ?
N1B C4B H411 . . 111.3 ?
C3B C4B H411 . . 111.3 ?
N1B C4B H412 . . 111.3 ?
C3B C4B H412 . . 111.3 ?
H411 C4B H412 . . 109.2 ?
F2B C5B F1B . . 106.72(18) ?
F2B C5B C2B . . 110.06(19) ?
F1B C5B C2B . . 112.24(18) ?
F2B C5B C6B . . 106.54(17) ?
F1B C5B C6B . . 105.73(19) ?
C2B C5B C6B . . 115.06(19) ?
F5B C6B F4B . . 108.51(19) ?
F5B C6B F3B . . 107.64(19) ?
F4B C6B F3B . . 108.3(2) ?
F5B C6B C5B . . 110.94(19) ?
F4B C6B C5B . . 110.3(2) ?
F3B C6B C5B . . 110.99(18) ?
O1B C7B N1B . . 124.35(19) ?
O1B C7B O2B . . 125.83(19) ?
N1B C7B O2B . . 109.82(16) ?
O2B C8B C9B . . 109.20(18) ?
O2B C8B C11B . . 102.11(16) ?
C9B C8B C11B . . 110.9(2) ?
O2B C8B C10B . . 110.62(18) ?
C9B C8B C10B . . 112.5(2) ?
C11B C8B C10B . . 111.1(2) ?
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 H10D . . 109.5 ?
C8B C10B H10E . . 109.5 ?
H10D C10B H10E . . 109.5 ?
C8B C10B H10F . . 109.5 ?
H10D C10B H10F . . 109.5 ?
H10E C10B H10F . . 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 ?
O3B C12B N2B . . 124.39(19) ?
O3B C12B C1B . . 121.26(19) ?
N2B C12B C1B . . 114.32(19) ?
N2B C13B C15B . . 111.22(17) ?
N2B C13B C14B . . 110.04(17) ?
C15B C13B C14B . . 113.02(17) ?
N2B C13B H13B . . 107.4 ?
C15B C13B H13B . . 107.4 ?
C14B C13B H13B . . 107.4 ?
O4B C14B C13B . . 110.55(18) ?
O4B C14B H14C . . 109.5 ?
C13B C14B H14C . . 109.5 ?
O4B C14B H14D . . 109.5 ?
C13B C14B H14D . . 109.5 ?
H14C C14B H14D . . 108.1 ?
C16B C15B C20B . . 118.8(2) ?
C16B C15B C13B . . 119.7(2) ?
C20B C15B C13B . . 121.52(19) ?
C15B C16B C17B . . 120.4(2) ?
C15B C16B H16B . . 119.8 ?
C17B C16B H16B . . 119.8 ?
C18B C17B C16B . . 120.5(2) ?
C18B C17B H17B . . 119.7 ?
C16B C17B H17B . . 119.7 ?
C17B C18B C19B . . 119.5(2) ?
C17B C18B H18B . . 120.2 ?
C19B C18B H18B . . 120.2 ?
C20B C19B C18B . . 120.2(2) ?
C20B C19B H19B . . 119.9 ?
C18B C19B H19B . . 119.9 ?
C19B C20B C15B . . 120.6(2) ?
C19B C20B H20B . . 119.7 ?
C15B C20B H20B . . 119.7 ?

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 C1A C12A . . . . -81.0(2) ?
C4A N1A C1A C12A . . . . 106.82(19) ?
C7A N1A C1A C2A . . . . 161.19(19) ?
C4A N1A C1A C2A . . . . -11.0(2) ?
N1A C1A C2A C5A . . . . -138.64(17) ?
C12A C1A C2A C5A . . . . 104.08(19) ?
N1A C1A C2A C3A . . . . -13.7(2) ?
C12A C1A C2A C3A . . . . -130.99(18) ?
C5A C2A C3A C4A . . . . 153.31(18) ?
C1A C2A C3A C4A . . . . 32.0(2) ?
C7A N1A C4A C3A . . . . -140.3(2) ?
C1A N1A C4A C3A . . . . 31.2(2) ?
C2A C3A C4A N1A . . . . -37.6(2) ?
C3A C2A C5A F1A . . . . -55.2(2) ?
C1A C2A C5A F1A . . . . 63.8(2) ?
C3A C2A C5A F2A . . . . -172.70(17) ?
C1A C2A C5A F2A . . . . -53.7(2) ?
C3A C2A C5A C6A . . . . 67.4(2) ?
C1A C2A C5A C6A . . . . -173.62(17) ?
F1A C5A C6A F3A . . . . 66.4(2) ?
F2A C5A C6A F3A . . . . 178.73(18) ?
C2A C5A C6A F3A . . . . -58.8(2) ?
F1A C5A C6A F4A . . . . -173.11(17) ?
F2A C5A C6A F4A . . . . -60.8(2) ?
C2A C5A C6A F4A . . . . 61.7(2) ?
F1A C5A C6A F5A . . . . -54.1(2) ?
F2A C5A C6A F5A . . . . 58.2(2) ?
C2A C5A C6A F5A . . . . -179.29(17) ?
C8A O2A C7A O1A . . . . -2.6(3) ?
C8A O2A C7A N1A . . . . 177.54(18) ?
C4A N1A C7A O1A . . . . 169.2(2) ?
C1A N1A C7A O1A . . . . -1.6(3) ?
C4A N1A C7A O2A . . . . -11.0(3) ?
C1A N1A C7A O2A . . . . 178.21(17) ?
C7A O2A C8A C10A . . . . -66.3(2) ?
C7A O2A C8A C11A . . . . 58.3(3) ?
C7A O2A C8A C9A . . . . 176.22(19) ?
C13A N2A C12A O3A . . . . 4.4(3) ?
C13A N2A C12A C1A . . . . -175.02(18) ?
N1A C1A C12A O3A . . . . -66.2(2) ?
C2A C1A C12A O3A . . . . 46.9(3) ?
N1A C1A C12A N2A . . . . 113.2(2) ?
C2A C1A C12A N2A . . . . -133.70(19) ?
C12A N2A C13A C15A . . . . 83.4(2) ?
C12A N2A C13A C14A . . . . -151.25(19) ?
N2A C13A C14A O4A . . . . -64.7(2) ?
C15A C13A C14A O4A . . . . 60.6(2) ?
N2A C13A C15A C16A . . . . 22.3(3) ?
C14A C13A C15A C16A . . . . -101.0(2) ?
N2A C13A C15A C20A . . . . -158.5(2) ?
C14A C13A C15A C20A . . . . 78.2(3) ?
C20A C15A C16A C17A . . . . -0.1(3) ?
C13A C15A C16A C17A . . . . 179.1(2) ?
C15A C16A C17A C18A . . . . 0.2(4) ?
C16A C17A C18A C19A . . . . -0.3(4) ?
C17A C18A C19A C20A . . . . 0.1(4) ?
C18A C19A C20A C15A . . . . 0.0(3) ?
C16A C15A C20A C19A . . . . -0.1(3) ?
C13A C15A C20A C19A . . . . -179.3(2) ?
C7B N1B C1B C12B . . . . -68.7(3) ?
C4B N1B C1B C12B . . . . 120.5(2) ?
C7B N1B C1B C2B . . . . 172.1(2) ?
C4B N1B C1B C2B . . . . 1.3(2) ?
N1B C1B C2B C5B . . . . -146.92(18) ?
C12B C1B C2B C5B . . . . 93.5(2) ?
N1B C1B C2B C3B . . . . -23.3(2) ?
C12B C1B C2B C3B . . . . -142.83(19) ?
C5B C2B C3B C4B . . . . 158.24(19) ?
C1B C2B C3B C4B . . . . 36.4(2) ?
C7B N1B C4B C3B . . . . -149.7(2) ?
C1B N1B C4B C3B . . . . 21.3(3) ?
C2B C3B C4B N1B . . . . -34.7(2) ?
C3B C2B C5B F2B . . . . 174.52(18) ?
C1B C2B C5B F2B . . . . -67.7(2) ?
C3B C2B C5B F1B . . . . -66.8(2) ?
C1B C2B C5B F1B . . . . 51.0(2) ?
C3B C2B C5B C6B . . . . 54.2(3) ?
C1B C2B C5B C6B . . . . 171.95(18) ?
F2B C5B C6B F5B . . . . 42.7(3) ?
F1B C5B C6B F5B . . . . -70.6(2) ?
C2B C5B C6B F5B . . . . 164.9(2) ?
F2B C5B C6B F4B . . . . -77.6(2) ?
F1B C5B C6B F4B . . . . 169.09(18) ?
C2B C5B C6B F4B . . . . 44.6(3) ?
F2B C5B C6B F3B . . . . 162.28(19) ?
F1B C5B C6B F3B . . . . 49.0(2) ?
C2B C5B C6B F3B . . . . -75.5(3) ?
C4B N1B C7B O1B . . . . -2.7(3) ?
C1B N1B C7B O1B . . . . -172.8(2) ?
C4B N1B C7B O2B . . . . 176.51(19) ?
C1B N1B C7B O2B . . . . 6.4(3) ?
C8B O2B C7B O1B . . . . -17.4(3) ?
C8B O2B C7B N1B . . . . 163.39(18) ?
C7B O2B C8B C9B . . . . -57.3(2) ?
C7B O2B C8B C11B . . . . -174.8(2) ?
C7B O2B C8B C10B . . . . 67.0(3) ?
C13B N2B C12B O3B . . . . -1.4(3) ?
C13B N2B C12B C1B . . . . 176.41(17) ?
N1B C1B C12B O3B . . . . -35.7(3) ?
C2B C1B C12B O3B . . . . 78.1(2) ?
N1B C1B C12B N2B . . . . 146.41(18) ?
C2B C1B C12B N2B . . . . -99.8(2) ?
C12B N2B C13B C15B . . . . 113.6(2) ?
C12B N2B C13B C14B . . . . -120.4(2) ?
N2B C13B C14B O4B . . . . -60.2(2) ?
C15B C13B C14B O4B . . . . 64.8(2) ?
N2B C13B C15B C16B . . . . -132.4(2) ?
C14B C13B C15B C16B . . . . 103.3(2) ?
N2B C13B C15B C20B . . . . 47.9(3) ?
C14B C13B C15B C20B . . . . -76.4(3) ?
C20B C15B C16B C17B . . . . -1.5(3) ?
C13B C15B C16B C17B . . . . 178.7(2) ?
C15B C16B C17B C18B . . . . 0.5(3) ?
C16B C17B C18B C19B . . . . 1.1(4) ?
C17B C18B C19B C20B . . . . -1.5(3) ?
C18B C19B C20B C15B . . . . 0.5(3) ?
C16B C15B C20B C19B . . . . 1.1(3) ?
C13B C15B C20B C19B . . . . -179.23(18) ?

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 H2C O3B . 0.81(3) 2.30(3) 3.065(3) 158.(2) ?
O4A H4A O3B . 0.87(3) 1.95(3) 2.817(2) 176.(3) ?
N2B H2D O3A 1_655 0.83(2) 2.14(2) 2.950(3) 163.(2) ?
O4B H4B O1B 3_746 0.88(3) 1.98(3) 2.846(2) 171.(3) ?


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

data_dan9441_2R3S-5b
_database_code_depnum_ccdc_archive 'CCDC 2193976'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-08-01 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 F5 N2 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         452.42
_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                   6.2877(3)
_cell_length_b                   16.4671(6)
_cell_length_c                   21.5393(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2230.18(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6415
_cell_measurement_theta_min      3.3784
_cell_measurement_theta_max      66.4573
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.224
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.036
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944

_exptl_absorpt_coefficient_mu    1.052
_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  0.79
_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            39243
_diffrn_reflns_av_R_equivalents  0.2419
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         66.86
_diffrn_reflns_theta_full        66.86
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25

_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.

The hydrogen atoms at N2 and O4 were refined freely.
;

_reflns_number_total             3960
_reflns_number_gt                2849
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0650
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1237
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.089
_refine_ls_number_reflns         3960
_refine_ls_number_parameters     292
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0210P)²+1.7196P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00098(17)
_refine_ls_abs_structure_details 
;

Flack x determined using 857 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(19)

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
N N1 0.4053(8) 0.4391(3) 0.3537(2) 0.0262(12) Uani d . . . 1 . .
N N2 0.3477(8) 0.3582(3) 0.5052(2) 0.0230(11) Uani d . . . 1 . .
H H2A 0.208(11) 0.337(4) 0.497(3) 0.04(2) Uiso d . . . 1 . .
O O1 0.3447(7) 0.3055(3) 0.33923(19) 0.0359(11) Uani d . . . 1 . .
O O2 0.5461(7) 0.3799(3) 0.27083(17) 0.0279(10) Uani d . . . 1 . .
O O3 0.6308(6) 0.4274(2) 0.46572(19) 0.0269(10) Uani d . . . 1 . .
O O4 0.4246(6) 0.1868(2) 0.52251(18) 0.0245(10) Uani d . . D 1 . .
H H4 0.339(10) 0.146(3) 0.522(3) 0.06(3) Uiso d . . D 1 . .
F F1 0.3460(6) 0.5581(2) 0.52386(15) 0.0314(8) Uani d . . . 1 . .
F F2 0.0268(5) 0.5131(2) 0.50467(16) 0.0321(9) Uani d . . . 1 . .
F F3 0.2449(7) 0.7020(2) 0.46761(19) 0.0472(11) Uani d . . . 1 . .
F F4 -0.0684(7) 0.6569(2) 0.44652(18) 0.0470(11) Uani d . . . 1 . .
F F5 0.0363(7) 0.6677(2) 0.54183(17) 0.0486(11) Uani d . . . 1 . .
C C1 0.2965(9) 0.4408(4) 0.4134(2) 0.0225(13) Uani d . . . 1 . .
H H1 0.1603 0.4095 0.4113 0.027 Uiso calc U . R 1 . .
C C2 0.2511(9) 0.5332(3) 0.4187(3) 0.0236(13) Uani d . . . 1 . .
H H2 0.1327 0.5459 0.3893 0.028 Uiso calc U . R 1 . .
C C3 0.4540(11) 0.5724(4) 0.3924(3) 0.0318(15) Uani d . . . 1 . .
H H3A 0.4239 0.6273 0.3758 0.038 Uiso calc U . R 1 . .
H H3B 0.5656 0.5766 0.4246 0.038 Uiso calc U . R 1 . .
C C4 0.5222(10) 0.5146(4) 0.3404(3) 0.0272(15) Uani d . . . 1 . .
H H4A 0.4826 0.5366 0.2992 0.033 Uiso calc U . R 1 . .
H H4B 0.6777 0.5052 0.3414 0.033 Uiso calc U . R 1 . .
C C5 0.1824(10) 0.5616(4) 0.4821(3) 0.0291(14) Uani d . . . 1 . .
C C6 0.0999(11) 0.6479(4) 0.4847(3) 0.0332(16) Uani d . . . 1 . .
C C7 0.4257(11) 0.3689(4) 0.3224(3) 0.0275(15) Uani d . . . 1 . .
C C8 0.5749(11) 0.3130(4) 0.2255(3) 0.0325(16) Uani d . . . 1 . .
C C9 0.3563(11) 0.2889(4) 0.1996(3) 0.0372(17) Uani d . . . 1 . .
H H9A 0.2716 0.2636 0.2325 0.056 Uiso calc U . R 1 . .
H H9B 0.3751 0.2503 0.1654 0.056 Uiso calc U . R 1 . .
H H9C 0.2828 0.3374 0.1843 0.056 Uiso calc U . R 1 . .
C C10 0.7096(11) 0.3516(5) 0.1759(3) 0.0397(19) Uani d . . . 1 . .
H H10A 0.6358 0.3993 0.1591 0.059 Uiso calc U . R 1 . .
H H10B 0.7347 0.3124 0.1425 0.059 Uiso calc U . R 1 . .
H H10C 0.846 0.3684 0.1938 0.059 Uiso calc U . R 1 . .
C C11 0.6904(12) 0.2420(4) 0.2556(3) 0.045(2) Uani d . . . 1 . .
H H11A 0.8233 0.2613 0.2743 0.068 Uiso calc U . R 1 . .
H H11B 0.7222 0.2008 0.2241 0.068 Uiso calc U . R 1 . .
H H11C 0.5999 0.2183 0.2879 0.068 Uiso calc U . R 1 . .
C C12 0.4393(10) 0.4071(4) 0.4644(3) 0.0240(13) Uani d . . . 1 . .
C C13 0.4593(10) 0.3236(4) 0.5592(3) 0.0228(13) Uani d . . . 1 . .
H H13 0.6131 0.318 0.5482 0.027 Uiso calc U . R 1 . .
C C14 0.3729(10) 0.2397(3) 0.5730(3) 0.0238(14) Uani d . . . 1 . .
H H14A 0.436 0.2187 0.6119 0.029 Uiso calc U . R 1 . .
H H14B 0.2167 0.2423 0.5783 0.029 Uiso calc U . R 1 . .
C C15 0.4436(10) 0.3773(4) 0.6155(3) 0.0232(13) Uani d . . . 1 . .
C C16 0.2618(11) 0.4216(4) 0.6291(3) 0.0323(16) Uani d . . . 1 . .
H H16 0.1441 0.4198 0.6015 0.039 Uiso calc U . R 1 . .
C C17 0.2500(12) 0.4688(4) 0.6828(3) 0.0356(17) Uani d . . . 1 . .
H H17 0.1248 0.499 0.6915 0.043 Uiso calc U . R 1 . .
C C18 0.4186(12) 0.4716(4) 0.7233(3) 0.0404(18) Uani d . . . 1 . .
H H18 0.4111 0.5039 0.7597 0.048 Uiso calc U . R 1 . .
C C19 0.5998(12) 0.4269(5) 0.7102(3) 0.0437(19) Uani d . . . 1 . .
H H19 0.7168 0.4282 0.7381 0.052 Uiso calc U . R 1 . .
C C20 0.6119(11) 0.3801(4) 0.6569(3) 0.0355(16) Uani d . . . 1 . .
H H20 0.737 0.3496 0.6487 0.043 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
N1 C7 . 1.345(8) ?
N1 C1 . 1.459(7) ?
N1 C4 . 1.472(7) ?
N2 C12 . 1.324(7) ?
N2 C13 . 1.472(7) ?
N2 H2A . 0.96(7) ?
O1 C7 . 1.216(7) ?
O2 C7 . 1.356(7) ?
O2 C8 . 1.483(7) ?
O3 C12 . 1.251(7) ?
O4 C14 . 1.430(7) ?
O4 H4 . 0.87(3) ?
F1 C5 . 1.367(7) ?
F2 C5 . 1.354(7) ?
F3 C6 . 1.328(7) ?
F4 C6 . 1.349(7) ?
F5 C6 . 1.333(7) ?
C1 C12 . 1.523(8) ?
C1 C2 . 1.552(8) ?
C1 H1 . 1.0 ?
C2 C5 . 1.508(8) ?
C2 C3 . 1.538(9) ?
C2 H2 . 1.0 ?
C3 C4 . 1.530(8) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.513(9) ?
C8 C10 . 1.503(9) ?
C8 C11 . 1.522(9) ?
C8 C9 . 1.536(9) ?
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 ?
C13 C15 . 1.503(8) ?
C13 C14 . 1.514(8) ?
C13 H13 . 1.0 ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C20 . 1.385(8) ?
C15 C16 . 1.387(8) ?
C16 C17 . 1.397(9) ?
C16 H16 . 0.95 ?
C17 C18 . 1.373(9) ?
C17 H17 . 0.95 ?
C18 C19 . 1.386(10) ?
C18 H18 . 0.95 ?
C19 C20 . 1.385(9) ?
C19 H19 . 0.95 ?
C20 H20 . 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
C7 N1 C1 . . 120.2(5) ?
C7 N1 C4 . . 125.6(5) ?
C1 N1 C4 . . 112.9(5) ?
C12 N2 C13 . . 123.5(5) ?
C12 N2 H2A . . 120.(4) ?
C13 N2 H2A . . 116.(4) ?
C7 O2 C8 . . 120.6(5) ?
C14 O4 H4 . . 110.(5) ?
N1 C1 C12 . . 110.7(5) ?
N1 C1 C2 . . 99.8(4) ?
C12 C1 C2 . . 114.4(5) ?
N1 C1 H1 . . 110.5 ?
C12 C1 H1 . . 110.5 ?
C2 C1 H1 . . 110.5 ?
C5 C2 C3 . . 116.2(5) ?
C5 C2 C1 . . 115.1(5) ?
C3 C2 C1 . . 103.4(5) ?
C5 C2 H2 . . 107.2 ?
C3 C2 H2 . . 107.2 ?
C1 C2 H2 . . 107.2 ?
C4 C3 C2 . . 103.9(5) ?
C4 C3 H3A . . 111.0 ?
C2 C3 H3A . . 111.0 ?
C4 C3 H3B . . 111.0 ?
C2 C3 H3B . . 111.0 ?
H3A C3 H3B . . 109.0 ?
N1 C4 C3 . . 104.1(5) ?
N1 C4 H4A . . 110.9 ?
C3 C4 H4A . . 110.9 ?
N1 C4 H4B . . 110.9 ?
C3 C4 H4B . . 110.9 ?
H4A C4 H4B . . 109.0 ?
F2 C5 F1 . . 106.4(5) ?
F2 C5 C2 . . 110.4(5) ?
F1 C5 C2 . . 111.5(5) ?
F2 C5 C6 . . 107.1(5) ?
F1 C5 C6 . . 105.9(5) ?
C2 C5 C6 . . 115.1(5) ?
F3 C6 F5 . . 107.4(5) ?
F3 C6 F4 . . 107.2(5) ?
F5 C6 F4 . . 107.5(5) ?
F3 C6 C5 . . 112.6(5) ?
F5 C6 C5 . . 111.5(5) ?
F4 C6 C5 . . 110.4(5) ?
O1 C7 N1 . . 123.2(6) ?
O1 C7 O2 . . 126.4(6) ?
N1 C7 O2 . . 110.4(5) ?
O2 C8 C10 . . 102.9(5) ?
O2 C8 C11 . . 110.3(5) ?
C10 C8 C11 . . 111.0(6) ?
O2 C8 C9 . . 108.8(5) ?
C10 C8 C9 . . 110.8(5) ?
C11 C8 C9 . . 112.5(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 N2 . . 124.5(6) ?
O3 C12 C1 . . 119.1(5) ?
N2 C12 C1 . . 116.4(5) ?
N2 C13 C15 . . 112.2(5) ?
N2 C13 C14 . . 109.6(5) ?
C15 C13 C14 . . 110.8(5) ?
N2 C13 H13 . . 108.0 ?
C15 C13 H13 . . 108.0 ?
C14 C13 H13 . . 108.0 ?
O4 C14 C13 . . 109.0(5) ?
O4 C14 H14A . . 109.9 ?
C13 C14 H14A . . 109.9 ?
O4 C14 H14B . . 109.9 ?
C13 C14 H14B . . 109.9 ?
H14A C14 H14B . . 108.3 ?
C20 C15 C16 . . 118.4(6) ?
C20 C15 C13 . . 119.3(6) ?
C16 C15 C13 . . 122.2(6) ?
C15 C16 C17 . . 120.7(6) ?
C15 C16 H16 . . 119.6 ?
C17 C16 H16 . . 119.6 ?
C18 C17 C16 . . 120.3(7) ?
C18 C17 H17 . . 119.9 ?
C16 C17 H17 . . 119.9 ?
C17 C18 C19 . . 119.2(6) ?
C17 C18 H18 . . 120.4 ?
C19 C18 H18 . . 120.4 ?
C20 C19 C18 . . 120.6(7) ?
C20 C19 H19 . . 119.7 ?
C18 C19 H19 . . 119.7 ?
C15 C20 C19 . . 120.7(7) ?
C15 C20 H20 . . 119.6 ?
C19 C20 H20 . . 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
C7 N1 C1 C12 . . . . 76.7(7) ?
C4 N1 C1 C12 . . . . -91.1(6) ?
C7 N1 C1 C2 . . . . -162.5(6) ?
C4 N1 C1 C2 . . . . 29.8(6) ?
N1 C1 C2 C5 . . . . -166.7(5) ?
C12 C1 C2 C5 . . . . -48.6(7) ?
N1 C1 C2 C3 . . . . -38.9(6) ?
C12 C1 C2 C3 . . . . 79.2(6) ?
C5 C2 C3 C4 . . . . 162.4(5) ?
C1 C2 C3 C4 . . . . 35.3(6) ?
C7 N1 C4 C3 . . . . -175.4(6) ?
C1 N1 C4 C3 . . . . -8.4(6) ?
C2 C3 C4 N1 . . . . -17.3(6) ?
C3 C2 C5 F2 . . . . -169.1(5) ?
C1 C2 C5 F2 . . . . -48.0(7) ?
C3 C2 C5 F1 . . . . -51.0(7) ?
C1 C2 C5 F1 . . . . 70.1(7) ?
C3 C2 C5 C6 . . . . 69.6(7) ?
C1 C2 C5 C6 . . . . -169.3(5) ?
F2 C5 C6 F3 . . . . 175.7(5) ?
F1 C5 C6 F3 . . . . 62.5(6) ?
C2 C5 C6 F3 . . . . -61.2(7) ?
F2 C5 C6 F5 . . . . 55.0(7) ?
F1 C5 C6 F5 . . . . -58.3(7) ?
C2 C5 C6 F5 . . . . 178.1(5) ?
F2 C5 C6 F4 . . . . -64.5(6) ?
F1 C5 C6 F4 . . . . -177.8(5) ?
C2 C5 C6 F4 . . . . 58.6(7) ?
C1 N1 C7 O1 . . . . 5.1(10) ?
C4 N1 C7 O1 . . . . 171.2(6) ?
C1 N1 C7 O2 . . . . -175.1(5) ?
C4 N1 C7 O2 . . . . -9.0(8) ?
C8 O2 C7 O1 . . . . 5.6(9) ?
C8 O2 C7 N1 . . . . -174.2(5) ?
C7 O2 C8 C10 . . . . 178.1(5) ?
C7 O2 C8 C11 . . . . -63.4(8) ?
C7 O2 C8 C9 . . . . 60.5(7) ?
C13 N2 C12 O3 . . . . 2.4(9) ?
C13 N2 C12 C1 . . . . -176.8(5) ?
N1 C1 C12 O3 . . . . 42.9(7) ?
C2 C1 C12 O3 . . . . -68.8(7) ?
N1 C1 C12 N2 . . . . -137.9(5) ?
C2 C1 C12 N2 . . . . 110.4(6) ?
C12 N2 C13 C15 . . . . 89.9(7) ?
C12 N2 C13 C14 . . . . -146.6(6) ?
N2 C13 C14 O4 . . . . 65.8(6) ?
C15 C13 C14 O4 . . . . -169.8(5) ?
N2 C13 C15 C20 . . . . -146.7(6) ?
C14 C13 C15 C20 . . . . 90.4(7) ?
N2 C13 C15 C16 . . . . 36.3(8) ?
C14 C13 C15 C16 . . . . -86.6(7) ?
C20 C15 C16 C17 . . . . 0.9(10) ?
C13 C15 C16 C17 . . . . 177.9(6) ?
C15 C16 C17 C18 . . . . -0.3(10) ?
C16 C17 C18 C19 . . . . -0.4(10) ?
C17 C18 C19 C20 . . . . 0.4(11) ?
C16 C15 C20 C19 . . . . -0.8(10) ?
C13 C15 C20 C19 . . . . -177.9(6) ?
C18 C19 C20 C15 . . . . 0.2(11) ?

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 H2A O4 4_456 0.96(7) 1.87(7) 2.825(6) 171.(6) ?
O4 H4 O3 4_456 0.87(3) 1.80(3) 2.648(6) 167.(7) ?


####################################################################### 
# 
# 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_dan9507_2S3R-5a
_database_code_depnum_ccdc_archive 'CCDC 2193975'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-08-01 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H25 F3 N2 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         402.41
_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                   10.8920(3)
_cell_length_b                   9.1572(3)
_cell_length_c                   20.2956(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.650(2)
_cell_angle_gamma                90
_cell_volume                     2022.12(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3021
_cell_measurement_theta_min      4.0630
_cell_measurement_theta_max      62.3524
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848

_exptl_absorpt_coefficient_mu    0.946
_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  0.76
_exptl_absorpt_correction_T_max  0.96

_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            27571
_diffrn_reflns_av_R_equivalents  0.0943
_diffrn_reflns_av_unetI/netI     0.0808
_diffrn_reflns_theta_min         4.06
_diffrn_reflns_theta_max         66.69
_diffrn_reflns_theta_full        66.69
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_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.

The hydrogen atoms at N2A, N2B, O4A and O4B were refined
freely, but with O-H distance restraints (DFIX). 

One OH group was found disordered over two positions in 
the asymmetric unit. Several restraints (SADI, SAME, 
ISOR and SIMU) were used in order to improve refinement
stability. 
;

_reflns_number_total             7110
_reflns_number_gt                5230
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_gt          0.1643
_refine_ls_wR_factor_ref         0.1822
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_number_reflns         7110
_refine_ls_number_parameters     535
_refine_ls_number_restraints     15
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1047P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.275
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.0(3)

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    '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
N N1A 0.2458(5) 0.3168(6) 0.5367(2) 0.0318(11) Uani d . . . 1.0 . .
N N2A -0.0827(5) 0.2619(6) 0.5177(3) 0.0303(11) Uani d . . . 1.0 . .
H H2C -0.071(7) 0.174(10) 0.508(4) 0.05(2) Uiso d . . . 1.0 . .
O O1A 0.0221(4) 0.4736(5) 0.5345(2) 0.0340(10) Uani d . . . 1.0 . .
O O2A 0.4023(4) 0.3508(5) 0.4684(2) 0.0378(10) Uani d . . . 1.0 . .
O O3A 0.2212(4) 0.2461(5) 0.4320(2) 0.0351(10) Uani d . . . 1.0 . .
O O4A -0.4066(4) 0.2773(5) 0.5610(2) 0.0404(11) Uani d . . D 1.0 . .
H H4A -0.447(9) 0.308(11) 0.527(3) 0.09(4) Uiso d . . D 1.0 . .
F F1A 0.0720(4) 0.1777(5) 0.73093(19) 0.0487(10) Uani d . . . 1.0 . .
F F2A -0.0414(3) 0.3125(4) 0.66624(18) 0.0413(9) Uani d . . . 1.0 . .
F F3A -0.0235(4) 0.0823(4) 0.6458(2) 0.0441(9) Uani d . . . 1.0 . .
C C2A 0.1306(5) 0.2461(7) 0.5521(3) 0.0289(13) Uani d . . . 1.0 . .
H H2A 0.1239 0.1484 0.5303 0.035 Uiso calc U . R 1.0 . .
C C3A 0.1499(6) 0.2277(7) 0.6278(3) 0.0328(14) Uani d . . . 1.0 . .
H H3A 0.2055 0.1419 0.6353 0.039 Uiso calc U . R 1.0 . .
C C4A 0.2232(6) 0.3631(7) 0.6488(3) 0.0360(14) Uani d . . . 1.0 . .
H H401 0.1691 0.4496 0.6515 0.043 Uiso calc U . R 1.0 . .
H H402 0.2669 0.3481 0.6922 0.043 Uiso calc U . R 1.0 . .
C C5A 0.3135(6) 0.3808(7) 0.5943(3) 0.0342(14) Uani d . . . 1.0 . .
H H501 0.3326 0.485 0.5868 0.041 Uiso calc U . R 1.0 . .
H H502 0.3908 0.3272 0.6048 0.041 Uiso calc U . R 1.0 . .
C C6A 0.0191(5) 0.3394(7) 0.5328(3) 0.0293(13) Uani d . . . 1.0 . .
C C7A 0.0395(6) 0.2008(7) 0.6662(3) 0.0363(14) Uani d . . . 1.0 . .
C C8A 0.2978(6) 0.3074(7) 0.4777(3) 0.0307(13) Uani d . . . 1.0 . .
C C9A 0.2584(7) 0.2281(7) 0.3630(3) 0.0398(15) Uani d . . . 1.0 . .
C C10A 0.3698(7) 0.1294(8) 0.3614(4) 0.0470(18) Uani d . . . 1.0 . .
H H10A 0.4407 0.1783 0.3832 0.07 Uiso calc U . R 1.0 . .
H H10B 0.3877 0.1082 0.3155 0.07 Uiso calc U . R 1.0 . .
H H10C 0.3532 0.038 0.3844 0.07 Uiso calc U . R 1.0 . .
C C11A 0.2823(6) 0.3766(7) 0.3328(3) 0.0383(15) Uani d . . . 1.0 . .
H H11A 0.2089 0.4378 0.3356 0.057 Uiso calc U . R 1.0 . .
H H11B 0.3016 0.3644 0.2864 0.057 Uiso calc U . R 1.0 . .
H H11C 0.3518 0.4234 0.3568 0.057 Uiso calc U . R 1.0 . .
C C12A 0.1446(7) 0.1590(8) 0.3302(3) 0.0472(18) Uani d . . . 1.0 . .
H H12A 0.1255 0.0681 0.353 0.071 Uiso calc U . R 1.0 . .
H H12B 0.1596 0.1377 0.2839 0.071 Uiso calc U . R 1.0 . .
H H12C 0.0751 0.2266 0.3324 0.071 Uiso calc U . R 1.0 . .
C C13A -0.2052(5) 0.3262(7) 0.5140(3) 0.0313(13) Uani d . . . 1.0 . .
H H13A -0.2028 0.4186 0.5403 0.038 Uiso calc U . R 1.0 . .
C C14A -0.2899(6) 0.2174(7) 0.5477(3) 0.0358(14) Uani d . . . 1.0 . .
H H14A -0.302 0.1307 0.519 0.043 Uiso calc U . R 1.0 . .
H H14B -0.249 0.1845 0.5897 0.043 Uiso calc U . R 1.0 . .
C C15A -0.2519(6) 0.3620(7) 0.4443(3) 0.0325(14) Uani d . . . 1.0 . .
C C16A -0.3468(6) 0.4628(7) 0.4350(3) 0.0364(14) Uani d . . . 1.0 . .
H H16A -0.3776 0.5129 0.4718 0.044 Uiso calc U . R 1.0 . .
C C17A -0.3966(6) 0.4903(8) 0.3714(4) 0.0416(16) Uani d . . . 1.0 . .
H H17A -0.4625 0.5576 0.3651 0.05 Uiso calc U . R 1.0 . .
C C18A -0.3504(7) 0.4202(8) 0.3183(4) 0.0471(18) Uani d . . . 1.0 . .
H H18A -0.3846 0.4388 0.2752 0.056 Uiso calc U . R 1.0 . .
C C19A -0.2539(7) 0.3221(8) 0.3271(4) 0.0464(17) Uani d . . . 1.0 . .
H H19A -0.2212 0.2753 0.29 0.056 Uiso calc U . R 1.0 . .
C C20A -0.2049(7) 0.2923(7) 0.3901(3) 0.0401(16) Uani d . . . 1.0 . .
H H20A -0.1394 0.2243 0.3961 0.048 Uiso calc U . R 1.0 . .
N N1B 0.5905(5) 0.6743(7) 0.1240(3) 0.0409(13) Uani d . . . 1.0 . .
N N2B 0.5171(5) 0.7239(6) -0.0505(2) 0.0341(12) Uani d . . . 1.0 . .
H H2D 0.507(7) 0.813(9) -0.046(3) 0.04(2) Uiso d . . . 1.0 . .
O O1B 0.5646(4) 0.5156(5) 0.0058(2) 0.0389(11) Uani d . . . 1.0 . .
O O2B 0.4852(5) 0.6270(6) 0.2149(2) 0.0565(15) Uani d . . . 1.0 . .
O O3B 0.3944(4) 0.7427(5) 0.1253(2) 0.0415(11) Uani d . . . 1.0 . .
F F1B 0.9220(4) 0.8503(6) 0.0121(3) 0.0636(13) Uani d . . . 1.0 . .
F F2B 0.7468(4) 0.9183(5) -0.0321(2) 0.0529(11) Uani d . . . 1.0 . .
F F3B 0.8072(4) 0.6950(5) -0.0416(2) 0.0521(11) Uani d . . . 1.0 . .
C C2B 0.6042(6) 0.7459(7) 0.0606(3) 0.0352(14) Uani d . . . 1.0 . .
H H2B 0.5593 0.8411 0.0594 0.042 Uiso calc U . R 1.0 . .
C C3B 0.7447(6) 0.7730(8) 0.0642(3) 0.0392(15) Uani d . . . 1.0 . .
H H3B 0.7603 0.8582 0.0942 0.047 Uiso calc U . R 1.0 . .
C C4B 0.7973(7) 0.6390(9) 0.0994(4) 0.0482(18) Uani d . . . 1.0 . .
H H411 0.8801 0.659 0.1195 0.058 Uiso calc U . R 1.0 . .
H H412 0.8022 0.5552 0.0688 0.058 Uiso calc U . R 1.0 . .
C C5B 0.7046(7) 0.6101(9) 0.1522(4) 0.0464(18) Uani d . . . 1.0 . .
H H511 0.6949 0.5041 0.1599 0.056 Uiso calc U . R 1.0 . .
H H512 0.7303 0.658 0.1943 0.056 Uiso calc U . R 1.0 . .
C C6B 0.5583(6) 0.6493(7) 0.0030(3) 0.0343(14) Uani d . . . 1.0 . .
C C7B 0.8035(6) 0.8068(8) 0.0011(4) 0.0454(17) Uani d . . . 1.0 . .
C C8B 0.4886(7) 0.6774(8) 0.1597(3) 0.0438(17) Uani d . . . 1.0 . .
C C9B 0.2751(6) 0.7629(8) 0.1568(3) 0.0405(16) Uani d . . . 1.0 . .
C C10B 0.2933(8) 0.8640(9) 0.2164(4) 0.059(2) Uani d . . . 1.0 . .
H H10D 0.3447 0.8151 0.2506 0.089 Uiso calc U . R 1.0 . .
H H10E 0.2133 0.8876 0.2338 0.089 Uiso calc U . R 1.0 . .
H H10F 0.3338 0.9541 0.2029 0.089 Uiso calc U . R 1.0 . .
C C11B 0.2197(8) 0.6183(8) 0.1749(4) 0.053(2) Uani d . . . 1.0 . .
H H11D 0.215 0.5547 0.136 0.08 Uiso calc U . R 1.0 . .
H H11E 0.137 0.6341 0.1905 0.08 Uiso calc U . R 1.0 . .
H H11F 0.2712 0.5721 0.2098 0.08 Uiso calc U . R 1.0 . .
C C12B 0.1987(7) 0.8378(10) 0.1026(4) 0.059(2) Uani d . . . 1.0 . .
H H12D 0.2416 0.9256 0.0883 0.088 Uiso calc U . R 1.0 . .
H H12E 0.1188 0.8654 0.1192 0.088 Uiso calc U . R 1.0 . .
H H12F 0.1861 0.7711 0.0651 0.088 Uiso calc U . R 1.0 . .
C C13B 0.4804(6) 0.6551(7) -0.1129(3) 0.0366(15) Uani d . . . 1.0 . .
H H13B 0.5148 0.5538 -0.1129 0.044 Uiso calc U . R 1.0 . .
C C14B 0.5366(6) 0.7407(8) -0.1690(3) 0.0415(16) Uani d . . D 1.0 . .
H H14C 0.5019 0.7029 -0.2116 0.05 Uiso calc U P R 0.726(13) A 1
H H14D 0.5119 0.8443 -0.1656 0.05 Uiso calc U P R 0.726(13) A 1
H H14E 0.6274 0.7348 -0.1651 0.05 Uiso calc U P R 0.274(13) A 2
H H14F 0.5084 0.6996 -0.2122 0.05 Uiso calc U P R 0.274(13) A 2
O O4B 0.6643(6) 0.7338(8) -0.1695(3) 0.045(2) Uani d U P D 0.726(13) A 1
H H4B 0.695 0.7762 -0.1359 0.067 Uiso calc U P R 0.726(13) A 1
O O4D 0.5007(17) 0.8775(16) -0.1642(9) 0.044(6) Uani d U P D 0.274(13) A 2
H H4D 0.536 0.9286 -0.1921 0.065 Uiso calc U P R 0.274(13) A 2
C C15B 0.3416(6) 0.6447(7) -0.1240(3) 0.0363(15) Uani d . . . 1.0 . .
C C16B 0.2920(7) 0.5649(8) -0.1777(4) 0.0437(17) Uani d . . . 1.0 . .
H H16B 0.3457 0.517 -0.2063 0.052 Uiso calc U . R 1.0 . .
C C17B 0.1652(7) 0.5546(8) -0.1900(4) 0.0480(19) Uani d . . . 1.0 . .
H H17B 0.133 0.5002 -0.2268 0.058 Uiso calc U . R 1.0 . .
C C18B 0.0872(7) 0.6235(9) -0.1487(4) 0.0511(19) Uani d . . . 1.0 . .
H H18B 0.0008 0.6172 -0.1569 0.061 Uiso calc U . R 1.0 . .
C C19B 0.1347(7) 0.7014(10) -0.0956(4) 0.056(2) Uani d . . . 1.0 . .
H H19B 0.0803 0.7484 -0.0671 0.068 Uiso calc U . R 1.0 . .
C C20B 0.2612(7) 0.7128(8) -0.0829(4) 0.0479(18) Uani d . . . 1.0 . .
H H20B 0.2923 0.7674 -0.046 0.057 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
N1A C8A . 1.351(8) ?
N1A C2A . 1.459(8) ?
N1A C5A . 1.475(8) ?
N2A C6A . 1.340(8) ?
N2A C13A . 1.457(8) ?
N2A H2C . 0.84(9) ?
O1A C6A . 1.230(8) ?
O2A C8A . 1.228(8) ?
O3A C8A . 1.342(8) ?
O3A C9A . 1.485(8) ?
O4A C14A . 1.422(8) ?
O4A H4A . 0.85(3) ?
F1A C7A . 1.362(8) ?
F2A C7A . 1.350(8) ?
F3A C7A . 1.340(8) ?
C2A C6A . 1.522(8) ?
C2A C3A . 1.550(9) ?
C2A H2A . 1.0 ?
C3A C7A . 1.483(9) ?
C3A C4A . 1.525(9) ?
C3A H3A . 1.0 ?
C4A C5A . 1.523(9) ?
C4A H401 . 0.99 ?
C4A H402 . 0.99 ?
C5A H501 . 0.99 ?
C5A H502 . 0.99 ?
C9A C10A . 1.514(10) ?
C9A C12A . 1.518(10) ?
C9A C11A . 1.519(9) ?
C10A H10A . 0.98 ?
C10A H10B . 0.98 ?
C10A H10C . 0.98 ?
C11A H11A . 0.98 ?
C11A H11B . 0.98 ?
C11A H11C . 0.98 ?
C12A H12A . 0.98 ?
C12A H12B . 0.98 ?
C12A H12C . 0.98 ?
C13A C15A . 1.517(9) ?
C13A C14A . 1.539(9) ?
C13A H13A . 1.0 ?
C14A H14A . 0.99 ?
C14A H14B . 0.99 ?
C15A C20A . 1.390(9) ?
C15A C16A . 1.392(9) ?
C16A C17A . 1.399(10) ?
C16A H16A . 0.95 ?
C17A C18A . 1.371(11) ?
C17A H17A . 0.95 ?
C18A C19A . 1.387(11) ?
C18A H18A . 0.95 ?
C19A C20A . 1.390(10) ?
C19A H19A . 0.95 ?
C20A H20A . 0.95 ?
N1B C8B . 1.353(9) ?
N1B C2B . 1.459(8) ?
N1B C5B . 1.467(9) ?
N2B C6B . 1.342(9) ?
N2B C13B . 1.456(8) ?
N2B H2D . 0.83(8) ?
O1B C6B . 1.227(8) ?
O2B C8B . 1.214(9) ?
O3B C8B . 1.354(9) ?
O3B C9B . 1.486(8) ?
F1B C7B . 1.359(8) ?
F2B C7B . 1.356(9) ?
F3B C7B . 1.342(8) ?
C2B C6B . 1.531(9) ?
C2B C3B . 1.548(9) ?
C2B H2B . 1.0 ?
C3B C7B . 1.491(10) ?
C3B C4B . 1.519(10) ?
C3B H3B . 1.0 ?
C4B C5B . 1.529(11) ?
C4B H411 . 0.99 ?
C4B H412 . 0.99 ?
C5B H511 . 0.99 ?
C5B H512 . 0.99 ?
C9B C11B . 1.507(10) ?
C9B C12B . 1.514(11) ?
C9B C10B . 1.528(11) ?
C10B H10D . 0.98 ?
C10B H10E . 0.98 ?
C10B H10F . 0.98 ?
C11B H11D . 0.98 ?
C11B H11E . 0.98 ?
C11B H11F . 0.98 ?
C12B H12D . 0.98 ?
C12B H12E . 0.98 ?
C12B H12F . 0.98 ?
C13B C15B . 1.521(10) ?
C13B C14B . 1.533(9) ?
C13B H13B . 1.0 ?
C14B O4D . 1.318(15) ?
C14B O4B . 1.392(9) ?
C14B H14C . 0.99 ?
C14B H14D . 0.99 ?
C14B H14E . 0.99 ?
C14B H14F . 0.99 ?
O4B H4B . 0.84 ?
O4D H4D . 0.84 ?
C15B C20B . 1.385(10) ?
C15B C16B . 1.401(10) ?
C16B C17B . 1.395(11) ?
C16B H16B . 0.95 ?
C17B C18B . 1.374(11) ?
C17B H17B . 0.95 ?
C18B C19B . 1.374(12) ?
C18B H18B . 0.95 ?
C19B C20B . 1.394(11) ?
C19B H19B . 0.95 ?
C20B H20B . 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
C8A N1A C2A . . 124.2(5) ?
C8A N1A C5A . . 120.9(5) ?
C2A N1A C5A . . 114.2(5) ?
C6A N2A C13A . . 123.0(5) ?
C6A N2A H2C . . 115.(5) ?
C13A N2A H2C . . 122.(5) ?
C8A O3A C9A . . 120.6(5) ?
C14A O4A H4A . . 115.(7) ?
N1A C2A C6A . . 112.3(5) ?
N1A C2A C3A . . 100.5(5) ?
C6A C2A C3A . . 112.8(5) ?
N1A C2A H2A . . 110.3 ?
C6A C2A H2A . . 110.3 ?
C3A C2A H2A . . 110.3 ?
C7A C3A C4A . . 114.5(5) ?
C7A C3A C2A . . 117.5(5) ?
C4A C3A C2A . . 103.5(5) ?
C7A C3A H3A . . 106.9 ?
C4A C3A H3A . . 106.9 ?
C2A C3A H3A . . 106.9 ?
C5A C4A C3A . . 103.3(5) ?
C5A C4A H401 . . 111.1 ?
C3A C4A H401 . . 111.1 ?
C5A C4A H402 . . 111.1 ?
C3A C4A H402 . . 111.1 ?
H401 C4A H402 . . 109.1 ?
N1A C5A C4A . . 102.6(5) ?
N1A C5A H501 . . 111.3 ?
C4A C5A H501 . . 111.3 ?
N1A C5A H502 . . 111.3 ?
C4A C5A H502 . . 111.3 ?
H501 C5A H502 . . 109.2 ?
O1A C6A N2A . . 123.8(6) ?
O1A C6A C2A . . 122.3(5) ?
N2A C6A C2A . . 113.8(5) ?
F3A C7A F2A . . 106.8(5) ?
F3A C7A F1A . . 106.2(5) ?
F2A C7A F1A . . 104.9(5) ?
F3A C7A C3A . . 112.9(6) ?
F2A C7A C3A . . 114.8(5) ?
F1A C7A C3A . . 110.6(5) ?
O2A C8A O3A . . 125.6(6) ?
O2A C8A N1A . . 123.0(6) ?
O3A C8A N1A . . 111.5(5) ?
O3A C9A C10A . . 109.9(6) ?
O3A C9A C12A . . 101.9(5) ?
C10A C9A C12A . . 112.4(6) ?
O3A C9A C11A . . 109.9(5) ?
C10A C9A C11A . . 111.9(6) ?
C12A C9A C11A . . 110.4(6) ?
C9A C10A H10A . . 109.5 ?
C9A C10A H10B . . 109.5 ?
H10A C10A H10B . . 109.5 ?
C9A C10A H10C . . 109.5 ?
H10A C10A H10C . . 109.5 ?
H10B C10A H10C . . 109.5 ?
C9A C11A H11A . . 109.5 ?
C9A C11A H11B . . 109.5 ?
H11A C11A H11B . . 109.5 ?
C9A C11A H11C . . 109.5 ?
H11A C11A H11C . . 109.5 ?
H11B C11A H11C . . 109.5 ?
C9A C12A H12A . . 109.5 ?
C9A C12A H12B . . 109.5 ?
H12A C12A H12B . . 109.5 ?
C9A C12A H12C . . 109.5 ?
H12A C12A H12C . . 109.5 ?
H12B C12A H12C . . 109.5 ?
N2A C13A C15A . . 113.7(5) ?
N2A C13A C14A . . 106.4(5) ?
C15A C13A C14A . . 111.8(5) ?
N2A C13A H13A . . 108.2 ?
C15A C13A H13A . . 108.2 ?
C14A C13A H13A . . 108.2 ?
O4A C14A C13A . . 113.2(5) ?
O4A C14A H14A . . 108.9 ?
C13A C14A H14A . . 108.9 ?
O4A C14A H14B . . 108.9 ?
C13A C14A H14B . . 108.9 ?
H14A C14A H14B . . 107.8 ?
C20A C15A C16A . . 119.7(6) ?
C20A C15A C13A . . 121.2(6) ?
C16A C15A C13A . . 119.0(6) ?
C15A C16A C17A . . 119.9(7) ?
C15A C16A H16A . . 120.0 ?
C17A C16A H16A . . 120.0 ?
C18A C17A C16A . . 120.0(7) ?
C18A C17A H17A . . 120.0 ?
C16A C17A H17A . . 120.0 ?
C17A C18A C19A . . 120.4(7) ?
C17A C18A H18A . . 119.8 ?
C19A C18A H18A . . 119.8 ?
C18A C19A C20A . . 120.1(7) ?
C18A C19A H19A . . 119.9 ?
C20A C19A H19A . . 119.9 ?
C15A C20A C19A . . 119.9(7) ?
C15A C20A H20A . . 120.1 ?
C19A C20A H20A . . 120.1 ?
C8B N1B C2B . . 125.7(6) ?
C8B N1B C5B . . 120.1(6) ?
C2B N1B C5B . . 113.9(5) ?
C6B N2B C13B . . 123.5(6) ?
C6B N2B H2D . . 117.(5) ?
C13B N2B H2D . . 119.(5) ?
C8B O3B C9B . . 119.4(5) ?
N1B C2B C6B . . 111.8(6) ?
N1B C2B C3B . . 99.9(5) ?
C6B C2B C3B . . 114.6(5) ?
N1B C2B H2B . . 110.1 ?
C6B C2B H2B . . 110.1 ?
C3B C2B H2B . . 110.1 ?
C7B C3B C4B . . 113.8(6) ?
C7B C3B C2B . . 117.1(6) ?
C4B C3B C2B . . 104.1(6) ?
C7B C3B H3B . . 107.1 ?
C4B C3B H3B . . 107.1 ?
C2B C3B H3B . . 107.1 ?
C3B C4B C5B . . 102.9(6) ?
C3B C4B H411 . . 111.2 ?
C5B C4B H411 . . 111.2 ?
C3B C4B H412 . . 111.2 ?
C5B C4B H412 . . 111.2 ?
H411 C4B H412 . . 109.1 ?
N1B C5B C4B . . 103.4(6) ?
N1B C5B H511 . . 111.1 ?
C4B C5B H511 . . 111.1 ?
N1B C5B H512 . . 111.1 ?
C4B C5B H512 . . 111.1 ?
H511 C5B H512 . . 109.0 ?
O1B C6B N2B . . 124.2(6) ?
O1B C6B C2B . . 121.7(6) ?
N2B C6B C2B . . 114.1(6) ?
F3B C7B F2B . . 106.3(6) ?
F3B C7B F1B . . 105.9(5) ?
F2B C7B F1B . . 105.6(6) ?
F3B C7B C3B . . 115.0(6) ?
F2B C7B C3B . . 112.2(6) ?
F1B C7B C3B . . 111.2(6) ?
O2B C8B N1B . . 123.2(7) ?
O2B C8B O3B . . 126.1(7) ?
N1B C8B O3B . . 110.8(6) ?
O3B C9B C11B . . 111.3(6) ?
O3B C9B C12B . . 101.9(5) ?
C11B C9B C12B . . 111.2(7) ?
O3B C9B C10B . . 109.3(6) ?
C11B C9B C10B . . 112.3(6) ?
C12B C9B C10B . . 110.3(7) ?
C9B C10B H10D . . 109.5 ?
C9B C10B H10E . . 109.5 ?
H10D C10B H10E . . 109.5 ?
C9B C10B H10F . . 109.5 ?
H10D C10B H10F . . 109.5 ?
H10E C10B H10F . . 109.5 ?
C9B C11B H11D . . 109.5 ?
C9B C11B H11E . . 109.5 ?
H11D C11B H11E . . 109.5 ?
C9B C11B H11F . . 109.5 ?
H11D C11B H11F . . 109.5 ?
H11E C11B H11F . . 109.5 ?
C9B C12B H12D . . 109.5 ?
C9B C12B H12E . . 109.5 ?
H12D C12B H12E . . 109.5 ?
C9B C12B H12F . . 109.5 ?
H12D C12B H12F . . 109.5 ?
H12E C12B H12F . . 109.5 ?
N2B C13B C15B . . 112.7(5) ?
N2B C13B C14B . . 108.8(5) ?
C15B C13B C14B . . 110.6(5) ?
N2B C13B H13B . . 108.2 ?
C15B C13B H13B . . 108.2 ?
C14B C13B H13B . . 108.2 ?
O4D C14B C13B . . 107.6(9) ?
O4B C14B C13B . . 114.6(6) ?
O4B C14B H14C . . 108.6 ?
C13B C14B H14C . . 108.6 ?
O4B C14B H14D . . 108.6 ?
C13B C14B H14D . . 108.6 ?
H14C C14B H14D . . 107.6 ?
O4D C14B H14E . . 110.2 ?
C13B C14B H14E . . 110.2 ?
O4D C14B H14F . . 110.2 ?
C13B C14B H14F . . 110.2 ?
H14E C14B H14F . . 108.5 ?
C14B O4B H4B . . 109.5 ?
C14B O4D H4D . . 109.5 ?
C20B C15B C16B . . 118.1(7) ?
C20B C15B C13B . . 122.4(6) ?
C16B C15B C13B . . 119.5(6) ?
C17B C16B C15B . . 121.2(7) ?
C17B C16B H16B . . 119.4 ?
C15B C16B H16B . . 119.4 ?
C18B C17B C16B . . 119.6(7) ?
C18B C17B H17B . . 120.2 ?
C16B C17B H17B . . 120.2 ?
C19B C18B C17B . . 119.8(7) ?
C19B C18B H18B . . 120.1 ?
C17B C18B H18B . . 120.1 ?
C18B C19B C20B . . 121.1(7) ?
C18B C19B H19B . . 119.4 ?
C20B C19B H19B . . 119.4 ?
C15B C20B C19B . . 120.1(7) ?
C15B C20B H20B . . 119.9 ?
C19B C20B H20B . . 119.9 ?

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
C8A N1A C2A C6A . . . . -86.6(7) ?
C5A N1A C2A C6A . . . . 103.0(6) ?
C8A N1A C2A C3A . . . . 153.2(6) ?
C5A N1A C2A C3A . . . . -17.1(6) ?
N1A C2A C3A C7A . . . . 161.9(5) ?
C6A C2A C3A C7A . . . . 42.1(8) ?
N1A C2A C3A C4A . . . . 34.5(6) ?
C6A C2A C3A C4A . . . . -85.3(6) ?
C7A C3A C4A C5A . . . . -169.3(5) ?
C2A C3A C4A C5A . . . . -40.1(6) ?
C8A N1A C5A C4A . . . . -177.8(6) ?
C2A N1A C5A C4A . . . . -7.1(7) ?
C3A C4A C5A N1A . . . . 28.9(6) ?
C13A N2A C6A O1A . . . . -12.0(9) ?
C13A N2A C6A C2A . . . . 164.2(5) ?
N1A C2A C6A O1A . . . . -32.3(8) ?
C3A C2A C6A O1A . . . . 80.5(7) ?
N1A C2A C6A N2A . . . . 151.5(5) ?
C3A C2A C6A N2A . . . . -95.8(6) ?
C4A C3A C7A F3A . . . . 179.1(5) ?
C2A C3A C7A F3A . . . . 57.2(7) ?
C4A C3A C7A F2A . . . . 56.4(7) ?
C2A C3A C7A F2A . . . . -65.5(7) ?
C4A C3A C7A F1A . . . . -62.1(7) ?
C2A C3A C7A F1A . . . . 176.0(5) ?
C9A O3A C8A O2A . . . . -1.3(9) ?
C9A O3A C8A N1A . . . . 178.6(5) ?
C2A N1A C8A O2A . . . . -169.8(6) ?
C5A N1A C8A O2A . . . . -0.1(10) ?
C2A N1A C8A O3A . . . . 10.3(8) ?
C5A N1A C8A O3A . . . . -180.0(5) ?
C8A O3A C9A C10A . . . . 61.8(8) ?
C8A O3A C9A C12A . . . . -178.8(6) ?
C8A O3A C9A C11A . . . . -61.8(7) ?
C6A N2A C13A C15A . . . . 98.8(7) ?
C6A N2A C13A C14A . . . . -137.7(6) ?
N2A C13A C14A O4A . . . . 167.1(5) ?
C15A C13A C14A O4A . . . . -68.1(7) ?
N2A C13A C15A C20A . . . . 22.4(8) ?
C14A C13A C15A C20A . . . . -98.1(7) ?
N2A C13A C15A C16A . . . . -159.9(6) ?
C14A C13A C15A C16A . . . . 79.6(7) ?
C20A C15A C16A C17A . . . . 1.9(10) ?
C13A C15A C16A C17A . . . . -175.8(6) ?
C15A C16A C17A C18A . . . . -1.3(10) ?
C16A C17A C18A C19A . . . . -0.2(11) ?
C17A C18A C19A C20A . . . . 1.2(11) ?
C16A C15A C20A C19A . . . . -0.9(10) ?
C13A C15A C20A C19A . . . . 176.8(6) ?
C18A C19A C20A C15A . . . . -0.7(11) ?
C8B N1B C2B C6B . . . . -86.7(8) ?
C5B N1B C2B C6B . . . . 100.6(7) ?
C8B N1B C2B C3B . . . . 151.7(7) ?
C5B N1B C2B C3B . . . . -21.0(7) ?
N1B C2B C3B C7B . . . . 163.1(6) ?
C6B C2B C3B C7B . . . . 43.5(8) ?
N1B C2B C3B C4B . . . . 36.5(7) ?
C6B C2B C3B C4B . . . . -83.1(7) ?
C7B C3B C4B C5B . . . . -167.9(6) ?
C2B C3B C4B C5B . . . . -39.3(7) ?
C8B N1B C5B C4B . . . . -175.8(7) ?
C2B N1B C5B C4B . . . . -2.6(8) ?
C3B C4B C5B N1B . . . . 25.8(7) ?
C13B N2B C6B O1B . . . . -3.1(10) ?
C13B N2B C6B C2B . . . . 173.8(6) ?
N1B C2B C6B O1B . . . . -31.2(9) ?
C3B C2B C6B O1B . . . . 81.5(8) ?
N1B C2B C6B N2B . . . . 151.8(6) ?
C3B C2B C6B N2B . . . . -95.5(7) ?
C4B C3B C7B F3B . . . . 52.5(8) ?
C2B C3B C7B F3B . . . . -69.2(8) ?
C4B C3B C7B F2B . . . . 174.1(6) ?
C2B C3B C7B F2B . . . . 52.4(8) ?
C4B C3B C7B F1B . . . . -67.8(8) ?
C2B C3B C7B F1B . . . . 170.5(6) ?
C2B N1B C8B O2B . . . . -173.3(7) ?
C5B N1B C8B O2B . . . . -1.0(12) ?
C2B N1B C8B O3B . . . . 6.8(10) ?
C5B N1B C8B O3B . . . . 179.1(6) ?
C9B O3B C8B O2B . . . . 2.6(11) ?
C9B O3B C8B N1B . . . . -177.5(6) ?
C8B O3B C9B C11B . . . . -61.3(9) ?
C8B O3B C9B C12B . . . . -180.0(7) ?
C8B O3B C9B C10B . . . . 63.3(8) ?
C6B N2B C13B C15B . . . . 102.6(7) ?
C6B N2B C13B C14B . . . . -134.4(6) ?
N2B C13B C14B O4D . . . . -56.1(11) ?
C15B C13B C14B O4D . . . . 68.1(11) ?
N2B C13B C14B O4B . . . . 66.6(8) ?
C15B C13B C14B O4B . . . . -169.1(6) ?
N2B C13B C15B C20B . . . . 8.6(9) ?
C14B C13B C15B C20B . . . . -113.4(7) ?
N2B C13B C15B C16B . . . . -172.0(6) ?
C14B C13B C15B C16B . . . . 66.0(8) ?
C20B C15B C16B C17B . . . . 0.3(10) ?
C13B C15B C16B C17B . . . . -179.1(6) ?
C15B C16B C17B C18B . . . . -0.1(11) ?
C16B C17B C18B C19B . . . . -0.2(12) ?
C17B C18B C19B C20B . . . . 0.4(13) ?
C16B C15B C20B C19B . . . . -0.2(11) ?
C13B C15B C20B C19B . . . . 179.2(7) ?
C18B C19B C20B C15B . . . . -0.2(13) ?

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 H2C O1A 2_546 0.84(9) 2.11(9) 2.932(7) 167.(8) ?
O4A H4A O2A 1_455 0.85(3) 2.02(5) 2.819(7) 157.(10) ?
O4B H4B F2B . 0.84 2.52 3.347(8) 169.4 ?


####################################################################### 
# 
# 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_dan9444_2S3R-5b
_database_code_depnum_ccdc_archive 'CCDC 2193977'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2022-08-01 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 F5 N2 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         452.42
_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                   9.1970(2)
_cell_length_b                   10.9472(2)
_cell_length_c                   21.0651(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2120.86(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9878
_cell_measurement_theta_min      4.0382
_cell_measurement_theta_max      68.3553
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.219
_exptl_crystal_size_min          0.134
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944

_exptl_absorpt_coefficient_mu    1.106
_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  0.80
_exptl_absorpt_correction_T_max  0.87

_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            15938
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_theta_min         4.55
_diffrn_reflns_theta_max         68.36
_diffrn_reflns_theta_full        68.36
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       19

_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.

The hydrogen atoms at N2 and O4 were refined freely. 
;

_reflns_number_total             3823
_reflns_number_gt                3716
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0608
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_refine_ls_number_reflns         3823
_refine_ls_number_parameters     291
_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)+(0.0293P)²+0.4271P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.160
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1534 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)

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 0.39783(12) 0.69004(9) 0.66029(5) 0.0206(2) Uani d . . . 1 . .
F F2 0.62790(12) 0.72094(10) 0.63916(5) 0.0217(2) Uani d . . . 1 . .
F F3 0.41770(13) 0.82905(11) 0.76500(5) 0.0296(3) Uani d . . . 1 . .
F F4 0.63976(15) 0.87487(13) 0.74402(6) 0.0370(3) Uani d . . . 1 . .
F F5 0.57892(15) 0.68837(11) 0.76118(6) 0.0349(3) Uani d . . . 1 . .
N N1 0.38831(16) 0.99182(12) 0.53825(7) 0.0124(3) Uani d . . . 1 . .
N N2 0.44680(16) 0.66690(13) 0.51895(7) 0.0121(3) Uani d . . . 1 . .
H H2A 0.539(3) 0.676(2) 0.5137(11) 0.022(6) Uiso d . . . 1 . .
O O1 0.35625(15) 1.15305(10) 0.47260(6) 0.0193(3) Uani d . . . 1 . .
O O2 0.46444(14) 0.97671(11) 0.43889(6) 0.0192(3) Uani d . . . 1 . .
O O3 0.23457(13) 0.76864(11) 0.53394(6) 0.0152(3) Uani d . . . 1 . .
O O4 0.43102(15) 0.34034(11) 0.56170(7) 0.0194(3) Uani d . . . 1 . .
H H4 0.415(3) 0.302(2) 0.5286(13) 0.033(7) Uiso d . . . 1 . .
C C1 0.45977(18) 0.87658(14) 0.55364(8) 0.0114(3) Uani d . . . 1 . .
H H1 0.5585 0.873 0.5338 0.014 Uiso calc U . R 1 . .
C C2 0.47266(19) 0.89006(15) 0.62702(8) 0.0126(4) Uani d . . . 1 . .
H H2 0.5542 0.9483 0.6353 0.015 Uiso calc U . R 1 . .
C C3 0.33151(19) 0.95589(15) 0.64524(8) 0.0142(4) Uani d . . . 1 . .
H H3A 0.2475 0.8993 0.6449 0.017 Uiso calc U . R 1 . .
H H3B 0.3393 0.9944 0.6876 0.017 Uiso calc U . R 1 . .
C C4 0.3187(2) 1.05187(16) 0.59279(8) 0.0160(4) Uani d . . . 1 . .
H H4A 0.2156 1.0713 0.5837 0.019 Uiso calc U . R 1 . .
H H4B 0.3703 1.1279 0.6045 0.019 Uiso calc U . R 1 . .
C C5 0.50631(19) 0.77457(16) 0.66352(9) 0.0147(4) Uani d . . . 1 . .
C C6 0.5364(2) 0.79260(17) 0.73459(10) 0.0206(4) Uani d . . . 1 . .
C C7 0.40027(18) 1.04940(15) 0.48184(9) 0.0137(4) Uani d . . . 1 . .
C C8 0.4814(2) 1.01586(19) 0.37197(9) 0.0222(4) Uani d . . . 1 . .
C C9 0.5794(2) 1.1270(3) 0.36800(11) 0.0380(6) Uani d . . . 1 . .
H H9A 0.5322 1.1964 0.389 0.057 Uiso calc U . R 1 . .
H H9B 0.5974 1.1471 0.3234 0.057 Uiso calc U . R 1 . .
H H9C 0.672 1.1093 0.3891 0.057 Uiso calc U . R 1 . .
C C10 0.3339(2) 1.03993(18) 0.34268(9) 0.0199(4) Uani d . . . 1 . .
H H10A 0.2714 0.9684 0.3488 0.03 Uiso calc U . R 1 . .
H H10B 0.3454 1.0559 0.2972 0.03 Uiso calc U . R 1 . .
H H10C 0.2894 1.1111 0.3631 0.03 Uiso calc U . R 1 . .
C C11 0.5494(3) 0.9026(3) 0.34286(10) 0.0437(7) Uani d . . . 1 . .
H H11A 0.6414 0.8845 0.3644 0.066 Uiso calc U . R 1 . .
H H11B 0.5678 0.9168 0.2976 0.066 Uiso calc U . R 1 . .
H H11C 0.483 0.8332 0.3478 0.066 Uiso calc U . R 1 . .
C C12 0.36815(19) 0.76598(15) 0.53312(8) 0.0110(3) Uani d . . . 1 . .
C C13 0.38331(18) 0.54449(15) 0.51633(9) 0.0127(3) Uani d . . . 1 . .
H H13 0.291 0.5454 0.5414 0.015 Uiso calc U . R 1 . .
C C14 0.4908(2) 0.45745(15) 0.54972(9) 0.0166(4) Uani d . . . 1 . .
H H14A 0.5785 0.4482 0.5229 0.02 Uiso calc U . R 1 . .
H H14B 0.5213 0.4944 0.5905 0.02 Uiso calc U . R 1 . .
C C15 0.34781(18) 0.50134(15) 0.44981(8) 0.0124(3) Uani d . . . 1 . .
C C16 0.24401(19) 0.40965(15) 0.44156(9) 0.0138(3) Uani d . . . 1 . .
H H16 0.1912 0.3803 0.4772 0.017 Uiso calc U . R 1 . .
C C17 0.2170(2) 0.36068(15) 0.38177(9) 0.0154(4) Uani d . . . 1 . .
H H17 0.1465 0.298 0.3767 0.018 Uiso calc U . R 1 . .
C C18 0.2932(2) 0.40362(18) 0.32961(9) 0.0198(4) Uani d . . . 1 . .
H H18 0.2757 0.3701 0.2887 0.024 Uiso calc U . R 1 . .
C C19 0.3955(2) 0.49612(18) 0.33735(9) 0.0221(4) Uani d . . . 1 . .
H H19 0.4471 0.5263 0.3015 0.026 Uiso calc U . R 1 . .
C C20 0.4227(2) 0.54446(17) 0.39699(9) 0.0178(4) Uani d . . . 1 . .
H H20 0.4928 0.6075 0.4018 0.021 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 C5 . 1.362(2) ?
F2 C5 . 1.363(2) ?
F3 C6 . 1.327(2) ?
F4 C6 . 1.325(2) ?
F5 C6 . 1.330(2) ?
N1 C7 . 1.350(2) ?
N1 C1 . 1.459(2) ?
N1 C4 . 1.470(2) ?
N2 C12 . 1.338(2) ?
N2 C13 . 1.463(2) ?
N2 H2A . 0.86(3) ?
O1 C7 . 1.220(2) ?
O2 C7 . 1.342(2) ?
O2 C8 . 1.482(2) ?
O3 C12 . 1.229(2) ?
O4 C14 . 1.417(2) ?
O4 H4 . 0.82(3) ?
C1 C12 . 1.537(2) ?
C1 C2 . 1.557(2) ?
C1 H1 . 1.0 ?
C2 C5 . 1.512(2) ?
C2 C3 . 1.534(2) ?
C2 H2 . 1.0 ?
C3 C4 . 1.529(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.535(3) ?
C8 C10 . 1.513(3) ?
C8 C9 . 1.517(3) ?
C8 C11 . 1.519(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 ?
C13 C15 . 1.514(2) ?
C13 C14 . 1.542(2) ?
C13 H13 . 1.0 ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C20 . 1.391(3) ?
C15 C16 . 1.396(2) ?
C16 C17 . 1.391(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.386(3) ?
C17 H17 . 0.95 ?
C18 C19 . 1.392(3) ?
C18 H18 . 0.95 ?
C19 C20 . 1.386(3) ?
C19 H19 . 0.95 ?
C20 H20 . 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
C7 N1 C1 . . 124.25(15) ?
C7 N1 C4 . . 120.97(14) ?
C1 N1 C4 . . 114.15(14) ?
C12 N2 C13 . . 122.37(14) ?
C12 N2 H2A . . 117.6(15) ?
C13 N2 H2A . . 119.9(15) ?
C7 O2 C8 . . 121.07(14) ?
C14 O4 H4 . . 111.8(18) ?
N1 C1 C12 . . 111.82(13) ?
N1 C1 C2 . . 99.96(13) ?
C12 C1 C2 . . 113.29(13) ?
N1 C1 H1 . . 110.5 ?
C12 C1 H1 . . 110.5 ?
C2 C1 H1 . . 110.5 ?
C5 C2 C3 . . 116.04(14) ?
C5 C2 C1 . . 116.18(14) ?
C3 C2 C1 . . 103.21(13) ?
C5 C2 H2 . . 106.9 ?
C3 C2 H2 . . 106.9 ?
C1 C2 H2 . . 106.9 ?
C4 C3 C2 . . 101.97(14) ?
C4 C3 H3A . . 111.4 ?
C2 C3 H3A . . 111.4 ?
C4 C3 H3B . . 111.4 ?
C2 C3 H3B . . 111.4 ?
H3A C3 H3B . . 109.2 ?
N1 C4 C3 . . 102.92(13) ?
N1 C4 H4A . . 111.2 ?
C3 C4 H4A . . 111.2 ?
N1 C4 H4B . . 111.2 ?
C3 C4 H4B . . 111.2 ?
H4A C4 H4B . . 109.1 ?
F1 C5 F2 . . 106.82(14) ?
F1 C5 C2 . . 113.12(14) ?
F2 C5 C2 . . 109.67(14) ?
F1 C5 C6 . . 105.54(14) ?
F2 C5 C6 . . 105.95(14) ?
C2 C5 C6 . . 115.18(15) ?
F4 C6 F3 . . 108.27(16) ?
F4 C6 F5 . . 108.00(16) ?
F3 C6 F5 . . 107.26(16) ?
F4 C6 C5 . . 111.27(15) ?
F3 C6 C5 . . 111.18(15) ?
F5 C6 C5 . . 110.70(16) ?
O1 C7 O2 . . 126.15(17) ?
O1 C7 N1 . . 123.20(17) ?
O2 C7 N1 . . 110.64(14) ?
O2 C8 C10 . . 110.13(15) ?
O2 C8 C9 . . 110.30(17) ?
C10 C8 C9 . . 111.77(17) ?
O2 C8 C11 . . 101.03(15) ?
C10 C8 C11 . . 110.31(19) ?
C9 C8 C11 . . 112.8(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 ?
O3 C12 N2 . . 124.26(16) ?
O3 C12 C1 . . 121.70(15) ?
N2 C12 C1 . . 113.89(14) ?
N2 C13 C15 . . 114.00(14) ?
N2 C13 C14 . . 107.04(14) ?
C15 C13 C14 . . 111.55(14) ?
N2 C13 H13 . . 108.0 ?
C15 C13 H13 . . 108.0 ?
C14 C13 H13 . . 108.0 ?
O4 C14 C13 . . 113.05(14) ?
O4 C14 H14A . . 109.0 ?
C13 C14 H14A . . 109.0 ?
O4 C14 H14B . . 109.0 ?
C13 C14 H14B . . 109.0 ?
H14A C14 H14B . . 107.8 ?
C20 C15 C16 . . 118.87(16) ?
C20 C15 C13 . . 121.85(15) ?
C16 C15 C13 . . 119.14(16) ?
C17 C16 C15 . . 120.79(17) ?
C17 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
C18 C17 C16 . . 119.79(17) ?
C18 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C17 C18 C19 . . 119.73(17) ?
C17 C18 H18 . . 120.1 ?
C19 C18 H18 . . 120.1 ?
C20 C19 C18 . . 120.37(18) ?
C20 C19 H19 . . 119.8 ?
C18 C19 H19 . . 119.8 ?
C19 C20 C15 . . 120.44(17) ?
C19 C20 H20 . . 119.8 ?
C15 C20 H20 . . 119.8 ?

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 C1 C12 . . . . -86.70(19) ?
C4 N1 C1 C12 . . . . 102.34(17) ?
C7 N1 C1 C2 . . . . 153.11(16) ?
C4 N1 C1 C2 . . . . -17.84(17) ?
N1 C1 C2 C5 . . . . 164.58(14) ?
C12 C1 C2 C5 . . . . 45.5(2) ?
N1 C1 C2 C3 . . . . 36.42(15) ?
C12 C1 C2 C3 . . . . -82.68(16) ?
C5 C2 C3 C4 . . . . -170.47(14) ?
C1 C2 C3 C4 . . . . -42.22(16) ?
C7 N1 C4 C3 . . . . -179.17(15) ?
C1 N1 C4 C3 . . . . -7.88(19) ?
C2 C3 C4 N1 . . . . 30.60(17) ?
C3 C2 C5 F1 . . . . 56.1(2) ?
C1 C2 C5 F1 . . . . -65.4(2) ?
C3 C2 C5 F2 . . . . 175.25(14) ?
C1 C2 C5 F2 . . . . 53.68(19) ?
C3 C2 C5 C6 . . . . -65.4(2) ?
C1 C2 C5 C6 . . . . 173.05(14) ?
F1 C5 C6 F4 . . . . -179.18(15) ?
F2 C5 C6 F4 . . . . 67.75(19) ?
C2 C5 C6 F4 . . . . -53.7(2) ?
F1 C5 C6 F3 . . . . -58.41(19) ?
F2 C5 C6 F3 . . . . -171.47(14) ?
C2 C5 C6 F3 . . . . 67.1(2) ?
F1 C5 C6 F5 . . . . 60.71(18) ?
F2 C5 C6 F5 . . . . -52.35(19) ?
C2 C5 C6 F5 . . . . -173.76(16) ?
C8 O2 C7 O1 . . . . -3.4(3) ?
C8 O2 C7 N1 . . . . 175.89(15) ?
C1 N1 C7 O1 . . . . -169.78(16) ?
C4 N1 C7 O1 . . . . 0.6(3) ?
C1 N1 C7 O2 . . . . 10.9(2) ?
C4 N1 C7 O2 . . . . -178.73(15) ?
C7 O2 C8 C10 . . . . -60.1(2) ?
C7 O2 C8 C9 . . . . 63.7(2) ?
C7 O2 C8 C11 . . . . -176.77(18) ?
C13 N2 C12 O3 . . . . -13.7(3) ?
C13 N2 C12 C1 . . . . 161.93(15) ?
N1 C1 C12 O3 . . . . -32.9(2) ?
C2 C1 C12 O3 . . . . 79.1(2) ?
N1 C1 C12 N2 . . . . 151.33(15) ?
C2 C1 C12 N2 . . . . -96.64(17) ?
C12 N2 C13 C15 . . . . 99.34(19) ?
C12 N2 C13 C14 . . . . -136.82(16) ?
N2 C13 C14 O4 . . . . 168.42(15) ?
C15 C13 C14 O4 . . . . -66.2(2) ?
N2 C13 C15 C20 . . . . 26.8(2) ?
C14 C13 C15 C20 . . . . -94.61(19) ?
N2 C13 C15 C16 . . . . -157.70(15) ?
C14 C13 C15 C16 . . . . 80.93(19) ?
C20 C15 C16 C17 . . . . 0.9(2) ?
C13 C15 C16 C17 . . . . -174.75(15) ?
C15 C16 C17 C18 . . . . -0.3(3) ?
C16 C17 C18 C19 . . . . -0.5(3) ?
C17 C18 C19 C20 . . . . 0.7(3) ?
C18 C19 C20 C15 . . . . -0.1(3) ?
C16 C15 C20 C19 . . . . -0.7(3) ?
C13 C15 C20 C19 . . . . 174.85(17) ?

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 H2A O3 4_566 0.86(3) 2.15(3) 2.9570(19) 157.(2) ?
O4 H4 O1 1_545 0.82(3) 2.09(3) 2.8634(19) 157.(2) ?



#=============================================================================
#  end of cif data for "dan9444 (compound 2S,3R-5b)"  
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================
