# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Final-P1
_database_code_depnum_ccdc_archive 'CCDC 2005098'
loop_
_audit_author_name
_audit_author_address
'Jerzy Klosin'
;The Dow Chemical Company
United States of America
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H52 F4 N4 O12'
_chemical_formula_weight         1024.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   8.5574(2)
_cell_length_b                   9.8938(2)
_cell_length_c                   14.8351(4)
_cell_angle_alpha                91.4030(10)
_cell_angle_beta                 93.6580(10)
_cell_angle_gamma                97.9200(10)
_cell_volume                     1240.80(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.02

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21191
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0164
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.376
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.869
_reflns_number_total             9654
_reflns_number_gt                9052
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.696
_reflns_Friedel_fraction_full    0.738

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0599P)²+0.1623P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 3514 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.09(17)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         9654
_refine_ls_number_parameters     675
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.3990(2) 0.60465(16) 0.67035(11) 0.0229(3) Uani 1 1 d . . . . .
O2 O 1.21232(18) 0.41150(15) 0.57479(10) 0.0194(3) Uani 1 1 d . . . . .
O3 O 1.4216(2) 0.3738(2) 0.49872(14) 0.0350(4) Uani 1 1 d . . . . .
O4 O 1.05282(19) 0.34677(16) 0.40921(12) 0.0236(3) Uani 1 1 d . . . . .
O5 O 0.69551(19) 0.35330(18) 0.37739(11) 0.0250(4) Uani 1 1 d . . . . .
O6 O 0.69397(18) 0.23498(17) 0.24539(11) 0.0233(3) Uani 1 1 d . . . . .
F1 F -0.11951(17) -0.21740(16) 0.25936(11) 0.0353(4) Uani 1 1 d . . . . .
F2 F 0.3459(3) 0.6407(3) 0.05079(19) 0.0807(9) Uani 1 1 d . . . . .
N1 N 1.1536(2) 0.7063(2) 0.43787(14) 0.0248(4) Uani 1 1 d . . . . .
N2 N 0.9657(2) 0.5223(2) 0.33531(14) 0.0240(4) Uani 1 1 d . . . . .
H2 H 0.9659 0.6113 0.3354 0.029 Uiso 1 1 calc R U . . .
C1 C 1.2405(3) 0.8031(2) 0.49040(18) 0.0271(5) Uani 1 1 d . . . . .
H1 H 1.2439 0.8948 0.4723 0.033 Uiso 1 1 calc R U . . .
C2 C 1.3264(3) 0.7800(2) 0.56963(17) 0.0238(5) Uani 1 1 d . . . . .
H2A H 1.3867 0.8535 0.6042 0.029 Uiso 1 1 calc R U . . .
C3 C 1.3216(3) 0.6466(2) 0.59680(15) 0.0190(4) Uani 1 1 d . . . . .
C4 C 1.2274(3) 0.5433(2) 0.54324(15) 0.0185(4) Uani 1 1 d . . . . .
C5 C 1.1485(3) 0.5763(2) 0.46429(15) 0.0193(4) Uani 1 1 d . . . . .
C6 C 1.4919(3) 0.7093(2) 0.72780(16) 0.0248(5) Uani 1 1 d . . . . .
H6A H 1.5744 0.7588 0.6935 0.037 Uiso 1 1 calc R U . . .
H6B H 1.5411 0.6672 0.7795 0.037 Uiso 1 1 calc R U . . .
H6C H 1.4234 0.7729 0.7496 0.037 Uiso 1 1 calc R U . . .
C7 C 1.3184(3) 0.3320(2) 0.54554(16) 0.0229(5) Uani 1 1 d . . . . .
C8 C 1.2844(3) 0.1908(2) 0.57962(19) 0.0316(6) Uani 1 1 d . . . . .
H8A H 1.1894 0.1424 0.5466 0.047 Uiso 1 1 calc R U . . .
H8B H 1.2672 0.1956 0.6442 0.047 Uiso 1 1 calc R U . . .
H8C H 1.3744 0.1417 0.5704 0.047 Uiso 1 1 calc R U . . .
C9 C 1.0519(3) 0.4695(2) 0.40131(15) 0.0201(4) Uani 1 1 d . . . . .
C10 C 0.8728(3) 0.4387(3) 0.26411(16) 0.0244(5) Uani 1 1 d . . . . .
H10 H 0.8144 0.5021 0.2279 0.029 Uiso 1 1 calc R U . . .
C11 C 0.9726(3) 0.3738(3) 0.19856(18) 0.0335(6) Uani 1 1 d . . . . .
H11A H 1.0484 0.4449 0.1743 0.050 Uiso 1 1 calc R U . . .
H11B H 0.9037 0.3267 0.1488 0.050 Uiso 1 1 calc R U . . .
H11C H 1.0300 0.3080 0.2303 0.050 Uiso 1 1 calc R U . . .
C12 C 0.7463(3) 0.3380(2) 0.30505(15) 0.0202(4) Uani 1 1 d . . . . .
C13 C 0.5595(3) 0.1342(2) 0.26496(17) 0.0238(5) Uani 1 1 d . . . . .
H13 H 0.5376 0.0707 0.2107 0.029 Uiso 1 1 calc R U . . .
C14 C 0.5992(3) 0.0477(3) 0.3436(2) 0.0386(7) Uani 1 1 d . . . . .
H14A H 0.7005 0.0149 0.3354 0.058 Uiso 1 1 calc R U . . .
H14B H 0.5160 -0.0304 0.3463 0.058 Uiso 1 1 calc R U . . .
H14C H 0.6070 0.1027 0.4000 0.058 Uiso 1 1 calc R U . . .
C15 C 0.4073(3) 0.1981(2) 0.27616(15) 0.0202(4) Uani 1 1 d . . . . .
H15 H 0.4140 0.2377 0.3392 0.024 Uiso 1 1 calc R U . . .
C16 C 0.2665(3) 0.0842(2) 0.26803(15) 0.0216(4) Uani 1 1 d . . . . .
C17 C 0.2447(3) -0.0187(3) 0.20071(18) 0.0316(6) Uani 1 1 d . . . . .
H17 H 0.3203 -0.0198 0.1566 0.038 Uiso 1 1 calc R U . . .
C18 C 0.1139(3) -0.1200(3) 0.19703(19) 0.0342(6) Uani 1 1 d . . . . .
H18 H 0.0986 -0.1892 0.1505 0.041 Uiso 1 1 calc R U . . .
C19 C 0.0086(3) -0.1170(3) 0.26199(17) 0.0267(5) Uani 1 1 d . . . . .
C20 C 0.0255(3) -0.0198(3) 0.33082(17) 0.0260(5) Uani 1 1 d . . . . .
H20 H -0.0491 -0.0218 0.3757 0.031 Uiso 1 1 calc R U . . .
C21 C 0.1550(3) 0.0813(2) 0.33263(16) 0.0224(4) Uani 1 1 d . . . . .
H21 H 0.1681 0.1504 0.3792 0.027 Uiso 1 1 calc R U . . .
C22 C 0.3895(3) 0.3136(3) 0.21254(17) 0.0240(5) Uani 1 1 d . . . . .
C23 C 0.3688(3) 0.2955(3) 0.11935(19) 0.0360(6) Uani 1 1 d . . . . .
H23 H 0.3648 0.2065 0.0929 0.043 Uiso 1 1 calc R U . . .
C24 C 0.3538(4) 0.4049(4) 0.0638(2) 0.0473(8) Uani 1 1 d . . . . .
H24 H 0.3391 0.3920 0.0000 0.057 Uiso 1 1 calc R U . . .
C25 C 0.3611(4) 0.5322(4) 0.1043(3) 0.0519(10) Uani 1 1 d . . . . .
C26 C 0.3789(4) 0.5550(3) 0.1959(3) 0.0558(10) Uani 1 1 d . . . . .
H26 H 0.3816 0.6442 0.2217 0.067 Uiso 1 1 calc R U . . .
C27 C 0.3932(3) 0.4438(3) 0.2506(2) 0.0389(7) Uani 1 1 d . . . . .
H27 H 0.4055 0.4574 0.3144 0.047 Uiso 1 1 calc R U . . .
O1' O -0.2946(2) -0.21533(17) 0.45491(11) 0.0259(4) Uani 1 1 d . . . . .
O2' O -0.12865(18) -0.01639(15) 0.55533(10) 0.0205(3) Uani 1 1 d . . . . .
O3' O -0.3258(2) 0.02712(19) 0.64039(14) 0.0335(4) Uani 1 1 d . . . . .
O4' O 0.0228(2) 0.05449(17) 0.72000(11) 0.0239(3) Uani 1 1 d . . . . .
O5' O 0.37749(19) 0.00803(17) 0.75104(11) 0.0252(4) Uani 1 1 d . . . . .
O6' O 0.39875(18) 0.16329(16) 0.86663(11) 0.0206(3) Uani 1 1 d . . . . .
F1' F 1.21944(17) 0.59032(16) 0.84480(12) 0.0364(4) Uani 1 1 d . . . . .
F2' F 0.7853(2) -0.26960(17) 1.04548(12) 0.0446(4) Uani 1 1 d . . . . .
N1' N -0.0726(2) -0.3063(2) 0.69744(14) 0.0228(4) Uani 1 1 d . . . . .
N2' N 0.0932(2) -0.1153(2) 0.80588(13) 0.0216(4) Uani 1 1 d . . . . .
H2' H 0.0818 -0.2033 0.8159 0.026 Uiso 1 1 calc R U . . .
C1' C -0.1503(3) -0.4065(3) 0.64299(18) 0.0267(5) Uani 1 1 d . . . . .
H1' H -0.1513 -0.4977 0.6618 0.032 Uiso 1 1 calc R U . . .
C2' C -0.2295(3) -0.3864(2) 0.56107(16) 0.0226(5) Uani 1 1 d . . . . .
H2'1 H -0.2851 -0.4614 0.5258 0.027 Uiso 1 1 calc R U . . .
C3' C -0.2253(3) -0.2538(2) 0.53178(15) 0.0203(4) Uani 1 1 d . . . . .
C4' C -0.1415(3) -0.1478(2) 0.58748(15) 0.0185(4) Uani 1 1 d . . . . .
C5' C -0.0692(3) -0.1776(2) 0.66943(15) 0.0191(4) Uani 1 1 d . . . . .
C6' C -0.3905(3) -0.3211(2) 0.39957(17) 0.0259(5) Uani 1 1 d . . . . .
H6'1 H -0.3257 -0.3907 0.3824 0.039 Uiso 1 1 calc R U . . .
H6'2 H -0.4332 -0.2815 0.3450 0.039 Uiso 1 1 calc R U . . .
H6'3 H -0.4779 -0.3632 0.4337 0.039 Uiso 1 1 calc R U . . .
C7' C -0.2238(3) 0.0682(2) 0.59212(16) 0.0215(4) Uani 1 1 d . . . . .
C8' C -0.1802(3) 0.2114(2) 0.56473(18) 0.0277(5) Uani 1 1 d . . . . .
H8'1 H -0.2730 0.2593 0.5655 0.042 Uiso 1 1 calc R U . . .
H8'2 H -0.1429 0.2114 0.5036 0.042 Uiso 1 1 calc R U . . .
H8'3 H -0.0961 0.2578 0.6070 0.042 Uiso 1 1 calc R U . . .
C9' C 0.0194(3) -0.0677(2) 0.73245(15) 0.0190(4) Uani 1 1 d . . . . .
C10' C 0.1912(3) -0.0191(2) 0.86771(15) 0.0218(5) Uani 1 1 d . . . . .
H10' H 0.1274 0.0518 0.8884 0.026 Uiso 1 1 calc R U . . .
C11' C 0.2519(4) -0.0916(3) 0.94987(17) 0.0349(6) Uani 1 1 d . . . . .
H11D H 0.1626 -0.1287 0.9842 0.052 Uiso 1 1 calc R U . . .
H11E H 0.3251 -0.0263 0.9885 0.052 Uiso 1 1 calc R U . . .
H11F H 0.3072 -0.1661 0.9297 0.052 Uiso 1 1 calc R U . . .
C12' C 0.3315(3) 0.0501(2) 0.81935(15) 0.0180(4) Uani 1 1 d . . . . .
C13' C 0.5460(2) 0.2342(2) 0.83504(15) 0.0201(4) Uani 1 1 d . . . . .
H13' H 0.5811 0.1810 0.7838 0.024 Uiso 1 1 calc R U . . .
C14' C 0.5134(3) 0.3726(3) 0.80438(18) 0.0268(5) Uani 1 1 d . . . . .
H14D H 0.4259 0.3611 0.7577 0.040 Uiso 1 1 calc R U . . .
H14E H 0.6083 0.4207 0.7796 0.040 Uiso 1 1 calc R U . . .
H14F H 0.4850 0.4257 0.8559 0.040 Uiso 1 1 calc R U . . .
C15' C 0.6667(2) 0.2411(2) 0.91651(15) 0.0186(4) Uani 1 1 d . . . . .
H15' H 0.6205 0.2861 0.9676 0.022 Uiso 1 1 calc R U . . .
C16' C 0.8195(3) 0.3318(2) 0.89801(15) 0.0203(4) Uani 1 1 d . . . . .
C17' C 0.9148(3) 0.2975(2) 0.83116(17) 0.0232(5) Uani 1 1 d . . . . .
H17' H 0.8870 0.2137 0.7976 0.028 Uiso 1 1 calc R U . . .
C18' C 1.0503(3) 0.3839(3) 0.81257(17) 0.0255(5) Uani 1 1 d . . . . .
H18' H 1.1151 0.3607 0.7665 0.031 Uiso 1 1 calc R U . . .
C19' C 1.0878(3) 0.5040(3) 0.86290(17) 0.0246(5) Uani 1 1 d . . . . .
C20' C 0.9986(3) 0.5409(3) 0.93005(18) 0.0289(5) Uani 1 1 d . . . . .
H20' H 1.0286 0.6240 0.9641 0.035 Uiso 1 1 calc R U . . .
C21' C 0.8623(3) 0.4536(2) 0.94739(16) 0.0240(5) Uani 1 1 d . . . . .
H21' H 0.7980 0.4778 0.9935 0.029 Uiso 1 1 calc R U . . .
C22' C 0.6957(3) 0.1003(2) 0.94743(15) 0.0191(4) Uani 1 1 d . . . . .
C23' C 0.7069(3) 0.0794(2) 1.04013(16) 0.0248(5) Uani 1 1 d . . . . .
H23' H 0.6938 0.1517 1.0811 0.030 Uiso 1 1 calc R U . . .
C24' C 0.7366(3) -0.0446(3) 1.07349(17) 0.0321(6) Uani 1 1 d . . . . .
H24' H 0.7438 -0.0581 1.1367 0.038 Uiso 1 1 calc R U . . .
C25' C 0.7556(3) -0.1477(3) 1.01308(18) 0.0286(5) Uani 1 1 d . . . . .
C26' C 0.7449(3) -0.1318(2) 0.92098(17) 0.0247(5) Uani 1 1 d . . . . .
H26' H 0.7577 -0.2048 0.8806 0.030 Uiso 1 1 calc R U . . .
C27' C 0.7149(3) -0.0068(2) 0.88849(15) 0.0222(5) Uani 1 1 d . . . . .
H27' H 0.7075 0.0058 0.8252 0.027 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.345(3) . ?
O1 C6 1.440(3) . ?
O2 C7 1.365(3) . ?
O2 C4 1.388(3) . ?
O3 C7 1.194(3) . ?
O4 C9 1.223(3) . ?
O5 C12 1.197(3) . ?
O6 C12 1.343(3) . ?
O6 C13 1.464(3) . ?
F1 C19 1.372(3) . ?
F2 C25 1.366(3) . ?
N1 C1 1.331(3) . ?
N1 C5 1.349(3) . ?
N2 C9 1.347(3) . ?
N2 C10 1.450(3) . ?
N2 H2 0.8800 . ?
C1 C2 1.387(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.406(3) . ?
C4 C5 1.383(3) . ?
C5 C9 1.512(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.494(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 C11 1.521(4) . ?
C10 C12 1.533(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C14 1.512(4) . ?
C13 C15 1.541(3) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C22 1.518(3) . ?
C15 C16 1.528(3) . ?
C15 H15 1.0000 . ?
C16 C21 1.392(3) . ?
C16 C17 1.394(4) . ?
C17 C18 1.393(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.364(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.372(4) . ?
C20 C21 1.385(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.387(4) . ?
C22 C27 1.389(4) . ?
C23 C24 1.392(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.368(6) . ?
C26 C27 1.397(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
O1' C3' 1.340(3) . ?
O1' C6' 1.442(3) . ?
O2' C7' 1.372(3) . ?
O2' C4' 1.389(3) . ?
O3' C7' 1.198(3) . ?
O4' C9' 1.224(3) . ?
O5' C12' 1.196(3) . ?
O6' C12' 1.345(3) . ?
O6' C13' 1.465(2) . ?
F1' C19' 1.362(3) . ?
F2' C25' 1.359(3) . ?
N1' C1' 1.337(3) . ?
N1' C5' 1.346(3) . ?
N2' C9' 1.351(3) . ?
N2' C10' 1.445(3) . ?
N2' H2' 0.8800 . ?
C1' C2' 1.385(4) . ?
C1' H1' 0.9500 . ?
C2' C3' 1.389(3) . ?
C2' H2'1 0.9500 . ?
C3' C4' 1.404(3) . ?
C4' C5' 1.385(3) . ?
C5' C9' 1.505(3) . ?
C6' H6'1 0.9800 . ?
C6' H6'2 0.9800 . ?
C6' H6'3 0.9800 . ?
C7' C8' 1.488(3) . ?
C8' H8'1 0.9800 . ?
C8' H8'2 0.9800 . ?
C8' H8'3 0.9800 . ?
C10' C12' 1.527(3) . ?
C10' C11' 1.528(3) . ?
C10' H10' 1.0000 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C13' C14' 1.509(3) . ?
C13' C15' 1.533(3) . ?
C13' H13' 1.0000 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C15' C16' 1.524(3) . ?
C15' C22' 1.525(3) . ?
C15' H15' 1.0000 . ?
C16' C21' 1.387(3) . ?
C16' C17' 1.388(3) . ?
C17' C18' 1.389(3) . ?
C17' H17' 0.9500 . ?
C18' C19' 1.376(4) . ?
C18' H18' 0.9500 . ?
C19' C20' 1.366(4) . ?
C20' C21' 1.394(3) . ?
C20' H20' 0.9500 . ?
C21' H21' 0.9500 . ?
C22' C27' 1.391(3) . ?
C22' C23' 1.395(3) . ?
C23' C24' 1.383(4) . ?
C23' H23' 0.9500 . ?
C24' C25' 1.375(4) . ?
C24' H24' 0.9500 . ?
C25' C26' 1.378(4) . ?
C26' C27' 1.389(3) . ?
C26' H26' 0.9500 . ?
C27' H27' 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C6 116.63(18) . . ?
C7 O2 C4 115.63(17) . . ?
C12 O6 C13 119.94(18) . . ?
C1 N1 C5 117.2(2) . . ?
C9 N2 C10 122.7(2) . . ?
C9 N2 H2 118.6 . . ?
C10 N2 H2 118.6 . . ?
N1 C1 C2 124.9(2) . . ?
N1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 H2A 121.0 . . ?
C1 C2 H2A 121.0 . . ?
O1 C3 C2 126.3(2) . . ?
O1 C3 C4 115.72(19) . . ?
C2 C3 C4 117.9(2) . . ?
C5 C4 O2 122.54(19) . . ?
C5 C4 C3 119.74(19) . . ?
O2 C4 C3 117.66(19) . . ?
N1 C5 C4 122.2(2) . . ?
N1 C5 C9 115.40(19) . . ?
C4 C5 C9 122.4(2) . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 O2 122.6(2) . . ?
O3 C7 C8 126.9(2) . . ?
O2 C7 C8 110.6(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 N2 123.3(2) . . ?
O4 C9 C5 123.2(2) . . ?
N2 C9 C5 113.57(19) . . ?
N2 C10 C11 113.5(2) . . ?
N2 C10 C12 109.87(19) . . ?
C11 C10 C12 114.5(2) . . ?
N2 C10 H10 106.1 . . ?
C11 C10 H10 106.1 . . ?
C12 C10 H10 106.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 O6 125.1(2) . . ?
O5 C12 C10 124.9(2) . . ?
O6 C12 C10 109.87(19) . . ?
O6 C13 C14 111.90(19) . . ?
O6 C13 C15 112.80(18) . . ?
C14 C13 C15 112.6(2) . . ?
O6 C13 H13 106.3 . . ?
C14 C13 H13 106.3 . . ?
C15 C13 H13 106.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C22 C15 C16 113.38(18) . . ?
C22 C15 C13 113.06(18) . . ?
C16 C15 C13 108.57(18) . . ?
C22 C15 H15 107.2 . . ?
C16 C15 H15 107.2 . . ?
C13 C15 H15 107.2 . . ?
C21 C16 C17 118.0(2) . . ?
C21 C16 C15 118.2(2) . . ?
C17 C16 C15 123.8(2) . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 118.2(3) . . ?
C19 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C18 C19 F1 118.5(2) . . ?
C18 C19 C20 123.3(2) . . ?
F1 C19 C20 118.3(2) . . ?
C19 C20 C21 117.8(2) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 H20 121.1 . . ?
C20 C21 C16 121.7(2) . . ?
C20 C21 H21 119.1 . . ?
C16 C21 H21 119.1 . . ?
C23 C22 C27 118.9(2) . . ?
C23 C22 C15 123.5(2) . . ?
C27 C22 C15 117.7(2) . . ?
C22 C23 C24 121.3(3) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C25 C24 C23 117.8(3) . . ?
C25 C24 H24 121.1 . . ?
C23 C24 H24 121.1 . . ?
F2 C25 C26 118.4(4) . . ?
F2 C25 C24 118.6(3) . . ?
C26 C25 C24 123.0(3) . . ?
C25 C26 C27 118.3(3) . . ?
C25 C26 H26 120.8 . . ?
C27 C26 H26 120.8 . . ?
C22 C27 C26 120.6(3) . . ?
C22 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C3' O1' C6' 116.78(18) . . ?
C7' O2' C4' 116.01(17) . . ?
C12' O6' C13' 116.97(17) . . ?
C1' N1' C5' 117.3(2) . . ?
C9' N2' C10' 118.88(19) . . ?
C9' N2' H2' 120.6 . . ?
C10' N2' H2' 120.6 . . ?
N1' C1' C2' 124.5(2) . . ?
N1' C1' H1' 117.8 . . ?
C2' C1' H1' 117.8 . . ?
C1' C2' C3' 118.3(2) . . ?
C1' C2' H2'1 120.9 . . ?
C3' C2' H2'1 120.9 . . ?
O1' C3' C2' 126.5(2) . . ?
O1' C3' C4' 115.7(2) . . ?
C2' C3' C4' 117.8(2) . . ?
C5' C4' O2' 122.50(19) . . ?
C5' C4' C3' 119.8(2) . . ?
O2' C4' C3' 117.68(19) . . ?
N1' C5' C4' 122.3(2) . . ?
N1' C5' C9' 115.77(19) . . ?
C4' C5' C9' 121.93(19) . . ?
O1' C6' H6'1 109.5 . . ?
O1' C6' H6'2 109.5 . . ?
H6'1 C6' H6'2 109.5 . . ?
O1' C6' H6'3 109.5 . . ?
H6'1 C6' H6'3 109.5 . . ?
H6'2 C6' H6'3 109.5 . . ?
O3' C7' O2' 122.2(2) . . ?
O3' C7' C8' 126.8(2) . . ?
O2' C7' C8' 111.0(2) . . ?
C7' C8' H8'1 109.5 . . ?
C7' C8' H8'2 109.5 . . ?
H8'1 C8' H8'2 109.5 . . ?
C7' C8' H8'3 109.5 . . ?
H8'1 C8' H8'3 109.5 . . ?
H8'2 C8' H8'3 109.5 . . ?
O4' C9' N2' 122.3(2) . . ?
O4' C9' C5' 123.5(2) . . ?
N2' C9' C5' 114.18(19) . . ?
N2' C10' C12' 109.39(18) . . ?
N2' C10' C11' 110.66(19) . . ?
C12' C10' C11' 109.4(2) . . ?
N2' C10' H10' 109.1 . . ?
C12' C10' H10' 109.1 . . ?
C11' C10' H10' 109.1 . . ?
C10' C11' H11D 109.5 . . ?
C10' C11' H11E 109.5 . . ?
H11D C11' H11E 109.5 . . ?
C10' C11' H11F 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
O5' C12' O6' 125.0(2) . . ?
O5' C12' C10' 125.2(2) . . ?
O6' C12' C10' 109.79(18) . . ?
O6' C13' C14' 107.48(18) . . ?
O6' C13' C15' 105.11(16) . . ?
C14' C13' C15' 113.56(19) . . ?
O6' C13' H13' 110.2 . . ?
C14' C13' H13' 110.2 . . ?
C15' C13' H13' 110.2 . . ?
C13' C14' H14D 109.5 . . ?
C13' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C13' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C16' C15' C22' 112.39(17) . . ?
C16' C15' C13' 110.84(17) . . ?
C22' C15' C13' 112.71(17) . . ?
C16' C15' H15' 106.8 . . ?
C22' C15' H15' 106.8 . . ?
C13' C15' H15' 106.8 . . ?
C21' C16' C17' 119.0(2) . . ?
C21' C16' C15' 119.3(2) . . ?
C17' C16' C15' 121.7(2) . . ?
C16' C17' C18' 121.0(2) . . ?
C16' C17' H17' 119.5 . . ?
C18' C17' H17' 119.5 . . ?
C19' C18' C17' 118.0(2) . . ?
C19' C18' H18' 121.0 . . ?
C17' C18' H18' 121.0 . . ?
F1' C19' C20' 118.4(2) . . ?
F1' C19' C18' 118.6(2) . . ?
C20' C19' C18' 122.9(2) . . ?
C19' C20' C21' 118.4(2) . . ?
C19' C20' H20' 120.8 . . ?
C21' C20' H20' 120.8 . . ?
C16' C21' C20' 120.6(2) . . ?
C16' C21' H21' 119.7 . . ?
C20' C21' H21' 119.7 . . ?
C27' C22' C23' 118.5(2) . . ?
C27' C22' C15' 123.6(2) . . ?
C23' C22' C15' 117.8(2) . . ?
C24' C23' C22' 121.2(2) . . ?
C24' C23' H23' 119.4 . . ?
C22' C23' H23' 119.4 . . ?
C25' C24' C23' 118.5(2) . . ?
C25' C24' H24' 120.7 . . ?
C23' C24' H24' 120.7 . . ?
F2' C25' C24' 118.8(2) . . ?
F2' C25' C26' 119.0(2) . . ?
C24' C25' C26' 122.3(2) . . ?
C25' C26' C27' 118.6(2) . . ?
C25' C26' H26' 120.7 . . ?
C27' C26' H26' 120.7 . . ?
C26' C27' C22' 120.9(2) . . ?
C26' C27' H27' 119.6 . . ?
C22' C27' H27' 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 0.4(4) . . . . ?
N1 C1 C2 C3 -0.3(4) . . . . ?
C6 O1 C3 C2 2.1(3) . . . . ?
C6 O1 C3 C4 -177.96(19) . . . . ?
C1 C2 C3 O1 178.7(2) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C7 O2 C4 C5 90.3(3) . . . . ?
C7 O2 C4 C3 -92.6(2) . . . . ?
O1 C3 C4 C5 -177.4(2) . . . . ?
C2 C3 C4 C5 2.6(3) . . . . ?
O1 C3 C4 O2 5.4(3) . . . . ?
C2 C3 C4 O2 -174.6(2) . . . . ?
C1 N1 C5 C4 1.1(3) . . . . ?
C1 N1 C5 C9 -178.5(2) . . . . ?
O2 C4 C5 N1 174.5(2) . . . . ?
C3 C4 C5 N1 -2.6(3) . . . . ?
O2 C4 C5 C9 -6.0(3) . . . . ?
C3 C4 C5 C9 176.9(2) . . . . ?
C4 O2 C7 O3 2.8(3) . . . . ?
C4 O2 C7 C8 -176.75(19) . . . . ?
C10 N2 C9 O4 -3.7(4) . . . . ?
C10 N2 C9 C5 175.82(19) . . . . ?
N1 C5 C9 O4 169.9(2) . . . . ?
C4 C5 C9 O4 -9.6(3) . . . . ?
N1 C5 C9 N2 -9.7(3) . . . . ?
C4 C5 C9 N2 170.8(2) . . . . ?
C9 N2 C10 C11 -68.6(3) . . . . ?
C9 N2 C10 C12 61.0(3) . . . . ?
C13 O6 C12 O5 3.2(3) . . . . ?
C13 O6 C12 C10 -172.84(18) . . . . ?
N2 C10 C12 O5 23.0(3) . . . . ?
C11 C10 C12 O5 152.1(2) . . . . ?
N2 C10 C12 O6 -160.97(19) . . . . ?
C11 C10 C12 O6 -31.9(3) . . . . ?
C12 O6 C13 C14 -67.2(3) . . . . ?
C12 O6 C13 C15 60.9(3) . . . . ?
O6 C13 C15 C22 36.6(3) . . . . ?
C14 C13 C15 C22 164.4(2) . . . . ?
O6 C13 C15 C16 163.31(18) . . . . ?
C14 C13 C15 C16 -68.9(3) . . . . ?
C22 C15 C16 C21 -100.9(2) . . . . ?
C13 C15 C16 C21 132.6(2) . . . . ?
C22 C15 C16 C17 80.6(3) . . . . ?
C13 C15 C16 C17 -46.0(3) . . . . ?
C21 C16 C17 C18 1.2(4) . . . . ?
C15 C16 C17 C18 179.8(2) . . . . ?
C16 C17 C18 C19 -1.0(4) . . . . ?
C17 C18 C19 F1 -179.3(2) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C18 C19 C20 C21 1.3(4) . . . . ?
F1 C19 C20 C21 -179.8(2) . . . . ?
C19 C20 C21 C16 -1.0(3) . . . . ?
C17 C16 C21 C20 -0.3(3) . . . . ?
C15 C16 C21 C20 -178.9(2) . . . . ?
C16 C15 C22 C23 -58.7(3) . . . . ?
C13 C15 C22 C23 65.4(3) . . . . ?
C16 C15 C22 C27 120.8(2) . . . . ?
C13 C15 C22 C27 -115.1(2) . . . . ?
C27 C22 C23 C24 0.8(4) . . . . ?
C15 C22 C23 C24 -179.7(2) . . . . ?
C22 C23 C24 C25 0.4(4) . . . . ?
C23 C24 C25 F2 -179.7(3) . . . . ?
C23 C24 C25 C26 -1.3(5) . . . . ?
F2 C25 C26 C27 179.5(3) . . . . ?
C24 C25 C26 C27 1.1(5) . . . . ?
C23 C22 C27 C26 -1.0(4) . . . . ?
C15 C22 C27 C26 179.4(3) . . . . ?
C25 C26 C27 C22 0.1(5) . . . . ?
C5' N1' C1' C2' -1.3(4) . . . . ?
N1' C1' C2' C3' 1.7(4) . . . . ?
C6' O1' C3' C2' 3.8(3) . . . . ?
C6' O1' C3' C4' -175.8(2) . . . . ?
C1' C2' C3' O1' -179.9(2) . . . . ?
C1' C2' C3' C4' -0.3(3) . . . . ?
C7' O2' C4' C5' -78.9(3) . . . . ?
C7' O2' C4' C3' 104.1(2) . . . . ?
O1' C3' C4' C5' 178.4(2) . . . . ?
C2' C3' C4' C5' -1.3(3) . . . . ?
O1' C3' C4' O2' -4.5(3) . . . . ?
C2' C3' C4' O2' 175.8(2) . . . . ?
C1' N1' C5' C4' -0.5(3) . . . . ?
C1' N1' C5' C9' -179.9(2) . . . . ?
O2' C4' C5' N1' -175.2(2) . . . . ?
C3' C4' C5' N1' 1.7(3) . . . . ?
O2' C4' C5' C9' 4.2(3) . . . . ?
C3' C4' C5' C9' -178.8(2) . . . . ?
C4' O2' C7' O3' -9.1(3) . . . . ?
C4' O2' C7' C8' 170.17(18) . . . . ?
C10' N2' C9' O4' -5.7(3) . . . . ?
C10' N2' C9' C5' 175.66(18) . . . . ?
N1' C5' C9' O4' -174.1(2) . . . . ?
C4' C5' C9' O4' 6.5(3) . . . . ?
N1' C5' C9' N2' 4.5(3) . . . . ?
C4' C5' C9' N2' -174.9(2) . . . . ?
C9' N2' C10' C12' -64.3(3) . . . . ?
C9' N2' C10' C11' 175.1(2) . . . . ?
C13' O6' C12' O5' -4.6(3) . . . . ?
C13' O6' C12' C10' 173.46(18) . . . . ?
N2' C10' C12' O5' -18.3(3) . . . . ?
C11' C10' C12' O5' 103.0(3) . . . . ?
N2' C10' C12' O6' 163.56(19) . . . . ?
C11' C10' C12' O6' -75.1(2) . . . . ?
C12' O6' C13' C14' 115.0(2) . . . . ?
C12' O6' C13' C15' -123.7(2) . . . . ?
O6' C13' C15' C16' -171.27(17) . . . . ?
C14' C13' C15' C16' -54.1(2) . . . . ?
O6' C13' C15' C22' 61.8(2) . . . . ?
C14' C13' C15' C22' 178.98(19) . . . . ?
C22' C15' C16' C21' -119.5(2) . . . . ?
C13' C15' C16' C21' 113.4(2) . . . . ?
C22' C15' C16' C17' 62.4(3) . . . . ?
C13' C15' C16' C17' -64.8(3) . . . . ?
C21' C16' C17' C18' -0.8(3) . . . . ?
C15' C16' C17' C18' 177.3(2) . . . . ?
C16' C17' C18' C19' 0.5(4) . . . . ?
C17' C18' C19' F1' -179.3(2) . . . . ?
C17' C18' C19' C20' 0.4(4) . . . . ?
F1' C19' C20' C21' 178.8(2) . . . . ?
C18' C19' C20' C21' -0.9(4) . . . . ?
C17' C16' C21' C20' 0.3(4) . . . . ?
C15' C16' C21' C20' -177.9(2) . . . . ?
C19' C20' C21' C16' 0.6(4) . . . . ?
C16' C15' C22' C27' -82.6(3) . . . . ?
C13' C15' C22' C27' 43.5(3) . . . . ?
C16' C15' C22' C23' 95.9(2) . . . . ?
C13' C15' C22' C23' -138.0(2) . . . . ?
C27' C22' C23' C24' 0.1(4) . . . . ?
C15' C22' C23' C24' -178.5(2) . . . . ?
C22' C23' C24' C25' 0.2(4) . . . . ?
C23' C24' C25' F2' 179.8(2) . . . . ?
C23' C24' C25' C26' -0.4(4) . . . . ?
F2' C25' C26' C27' -179.8(2) . . . . ?
C24' C25' C26' C27' 0.4(4) . . . . ?
C25' C26' C27' C22' -0.2(4) . . . . ?
C23' C22' C27' C26' -0.1(3) . . . . ?
C15' C22' C27' C26' 178.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8' H8'2 O4 0.98 2.52 3.331(3) 140.4 1_455
C6' H6'1 O5 0.98 2.56 3.414(3) 145.1 1_445
N2' H2' F1' 0.88 2.53 3.295(3) 146.3 1_445
C14 H14C O5 0.98 2.53 3.043(3) 112.7 .
C6 H6C O5' 0.98 2.41 3.257(3) 144.1 1_665
C2 H2A O5' 0.95 2.64 3.436(3) 141.3 1_665
N2 H2 F1 0.88 2.24 2.998(3) 144.4 1_665
C8' H8'2 O4 0.98 2.52 3.331(3) 140.4 1_455
C6' H6'1 O5 0.98 2.56 3.414(3) 145.1 1_445
N2' H2' F1' 0.88 2.53 3.295(3) 146.3 1_445
C14 H14C O5 0.98 2.53 3.043(3) 112.7 .
C6 H6C O5' 0.98 2.41 3.257(3) 144.1 1_665
C2 H2A O5' 0.95 2.64 3.436(3) 141.3 1_665
N2 H2 F1 0.88 2.24 2.998(3) 144.4 1_665
C8' H8'2 O4 0.98 2.52 3.331(3) 140.4 1_455
C6' H6'1 O5 0.98 2.56 3.414(3) 145.1 1_445
N2' H2' F1' 0.88 2.53 3.295(3) 146.3 1_445
C14 H14C O5 0.98 2.53 3.043(3) 112.7 .
C6 H6C O5' 0.98 2.41 3.257(3) 144.1 1_665
C2 H2A O5' 0.95 2.64 3.436(3) 141.3 1_665
N2 H2 F1 0.88 2.24 2.998(3) 144.4 1_665
C8' H8'2 O4 0.98 2.52 3.331(3) 140.4 1_455
C6' H6'1 O5 0.98 2.56 3.414(3) 145.1 1_445
N2' H2' F1' 0.88 2.53 3.295(3) 146.3 1_445
C14 H14C O5 0.98 2.53 3.043(3) 112.7 .
C6 H6C O5' 0.98 2.41 3.257(3) 144.1 1_665
C2 H2A O5' 0.95 2.64 3.436(3) 141.3 1_665
N2 H2 F1 0.88 2.24 2.998(3) 144.4 1_665
N2 H2 F1 0.88 2.24 2.998(3) 144.4 1_665
C2 H2A O5' 0.95 2.64 3.436(3) 141.3 1_665
C6 H6C O5' 0.98 2.41 3.257(3) 144.1 1_665
C14 H14C O5 0.98 2.53 3.043(3) 112.7 .
N2' H2' F1' 0.88 2.53 3.295(3) 146.3 1_445
C6' H6'1 O5 0.98 2.56 3.414(3) 145.1 1_445
C8' H8'2 O4 0.98 2.52 3.331(3) 140.4 1_455
N2 H2 F1 0.88 2.24 2.998(3) 144.4 1_665
C2 H2A O5' 0.95 2.64 3.436(3) 141.3 1_665
C6 H6C O5' 0.98 2.41 3.257(3) 144.1 1_665
C14 H14C O5 0.98 2.53 3.043(3) 112.7 .
N2' H2' F1' 0.88 2.53 3.295(3) 146.3 1_445
C6' H6'1 O5 0.98 2.56 3.414(3) 145.1 1_445
C8' H8'2 O4 0.98 2.52 3.331(3) 140.4 1_455
N2 H2 F1 0.88 2.24 2.998(3) 144.4 1_665
C2 H2A O5' 0.95 2.64 3.436(3) 141.3 1_665
C6 H6C O5' 0.98 2.41 3.257(3) 144.1 1_665
C14 H14C O5 0.98 2.53 3.043(3) 112.7 .
N2' H2' F1' 0.88 2.53 3.295(3) 146.3 1_445
C6' H6'1 O5 0.98 2.56 3.414(3) 145.1 1_445
C8' H8'2 O4 0.98 2.52 3.331(3) 140.4 1_455
N2 H2 F1 0.88 2.24 2.998(3) 144.4 1_665
C2 H2A O5' 0.95 2.64 3.436(3) 141.3 1_665
C6 H6C O5' 0.98 2.41 3.257(3) 144.1 1_665
C14 H14C O5 0.98 2.53 3.043(3) 112.7 .
N2' H2' F1' 0.88 2.53 3.295(3) 146.3 1_445
C6' H6'1 O5 0.98 2.56 3.414(3) 145.1 1_445
C8' H8'2 O4 0.98 2.52 3.331(3) 140.4 1_455

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_Final
_database_code_depnum_ccdc_archive 'CCDC 2005099'
loop_
_audit_author_name
_audit_author_address
'Jerzy Klosin'
;The Dow Chemical Company
United States of America
;
_audit_update_record             
;
2020-05-21 deposited with the CCDC.	2020-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H36 Cl F2 N O4'
_chemical_formula_weight         475.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3081(3)
_cell_length_b                   11.7497(4)
_cell_length_c                   26.4644(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2583.39(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5450
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13605
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.539
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5864
_reflns_number_gt                5181
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.992

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²+0.6515P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1964 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.00(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5864
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0827
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.83292(7) 0.70552(5) 0.42526(2) 0.02143(14) Uani 1 1 d . . . . .
F1 F -0.3360(2) 0.28168(16) 0.29280(5) 0.0339(4) Uani 1 1 d . . . . .
F2 F 0.0124(2) 0.35249(16) 0.62117(6) 0.0372(4) Uani 1 1 d . . . . .
N1 N 0.6301(2) 0.67154(17) 0.52407(8) 0.0174(4) Uani 1 1 d . . . . .
H1A H 0.6903 0.7079 0.5003 0.026 Uiso 1 1 calc R U . . .
H1B H 0.6897 0.6618 0.5526 0.026 Uiso 1 1 calc R U . . .
H1C H 0.5415 0.7140 0.5313 0.026 Uiso 1 1 calc R U . . .
O1 O 0.3860(2) 0.66617(15) 0.45607(6) 0.0222(4) Uani 1 1 d . . . . .
O2 O 0.4318(2) 0.48162(14) 0.43758(6) 0.0187(4) Uani 1 1 d . . . . .
O3 O 0.0513(2) 0.7383(2) 0.65110(7) 0.0372(5) Uani 1 1 d . . . . .
H3 H 0.1261 0.7487 0.6302 0.056 Uiso 1 1 calc R U . . .
O4 O 0.7763(2) 0.63483(17) 0.61692(6) 0.0258(4) Uani 1 1 d . . . . .
H4 H 0.8637 0.6638 0.6264 0.039 Uiso 1 1 calc R U . . .
C1 C 0.4552(3) 0.5779(2) 0.46295(9) 0.0160(5) Uani 1 1 d . . . . .
C2 C 0.5793(3) 0.55869(19) 0.50439(9) 0.0171(5) Uani 1 1 d . . . . .
H2 H 0.6747 0.5183 0.4900 0.021 Uiso 1 1 calc R U . . .
C3 C 0.5064(3) 0.4869(2) 0.54679(10) 0.0234(6) Uani 1 1 d . . . . .
H3A H 0.5877 0.4738 0.5730 0.035 Uiso 1 1 calc R U . . .
H3B H 0.4706 0.4136 0.5331 0.035 Uiso 1 1 calc R U . . .
H3C H 0.4143 0.5272 0.5615 0.035 Uiso 1 1 calc R U . . .
C4 C 0.2964(3) 0.4773(2) 0.40197(8) 0.0174(5) Uani 1 1 d . . . . .
H4A H 0.2264 0.5458 0.4064 0.021 Uiso 1 1 calc R U . . .
C5 C 0.3638(3) 0.4744(2) 0.34899(10) 0.0246(6) Uani 1 1 d . . . . .
H5A H 0.4292 0.5425 0.3432 0.037 Uiso 1 1 calc R U . . .
H5B H 0.2751 0.4723 0.3246 0.037 Uiso 1 1 calc R U . . .
H5C H 0.4308 0.4064 0.3448 0.037 Uiso 1 1 calc R U . . .
C6 C 0.2029(3) 0.36950(19) 0.41633(9) 0.0161(5) Uani 1 1 d . . . . .
H6 H 0.2780 0.3039 0.4114 0.019 Uiso 1 1 calc R U . . .
C7 C 0.0600(3) 0.3492(2) 0.38175(8) 0.0166(5) Uani 1 1 d . . . . .
C8 C 0.0393(3) 0.2429(2) 0.35938(9) 0.0209(5) Uani 1 1 d . . . . .
H8 H 0.1176 0.1852 0.3648 0.025 Uiso 1 1 calc R U . . .
C9 C -0.0933(3) 0.2196(2) 0.32940(9) 0.0251(6) Uani 1 1 d . . . . .
H9 H -0.1071 0.1467 0.3145 0.030 Uiso 1 1 calc R U . . .
C10 C -0.2043(3) 0.3042(2) 0.32168(9) 0.0246(6) Uani 1 1 d . . . . .
C11 C -0.1874(3) 0.4113(2) 0.34193(9) 0.0235(5) Uani 1 1 d . . . . .
H11 H -0.2646 0.4690 0.3352 0.028 Uiso 1 1 calc R U . . .
C12 C -0.0546(3) 0.4333(2) 0.37244(9) 0.0198(5) Uani 1 1 d . . . . .
H12 H -0.0419 0.5065 0.3871 0.024 Uiso 1 1 calc R U . . .
C13 C 0.1537(3) 0.3687(2) 0.47201(9) 0.0169(5) Uani 1 1 d . . . . .
C14 C 0.0653(3) 0.4569(2) 0.49355(9) 0.0215(5) Uani 1 1 d . . . . .
H14 H 0.0359 0.5208 0.4736 0.026 Uiso 1 1 calc R U . . .
C15 C 0.0194(3) 0.4524(2) 0.54428(10) 0.0252(6) Uani 1 1 d . . . . .
H15 H -0.0392 0.5131 0.5592 0.030 Uiso 1 1 calc R U . . .
C16 C 0.0608(3) 0.3587(2) 0.57195(9) 0.0248(6) Uani 1 1 d . . . . .
C17 C 0.1487(3) 0.2701(2) 0.55266(9) 0.0240(6) Uani 1 1 d . . . . .
H17 H 0.1769 0.2067 0.5731 0.029 Uiso 1 1 calc R U . . .
C18 C 0.1954(3) 0.2760(2) 0.50206(10) 0.0208(5) Uani 1 1 d . . . . .
H18 H 0.2567 0.2157 0.4879 0.025 Uiso 1 1 calc R U . . .
C19 C 0.1172(4) 0.6987(3) 0.69793(12) 0.0419(8) Uani 1 1 d . . . . .
H19 H 0.0235 0.6797 0.7201 0.050 Uiso 1 1 calc R U . . .
C20 C 0.2073(4) 0.5904(3) 0.69002(14) 0.0473(9) Uani 1 1 d . . . . .
H20A H 0.1355 0.5335 0.6751 0.071 Uiso 1 1 calc R U . . .
H20B H 0.2475 0.5625 0.7226 0.071 Uiso 1 1 calc R U . . .
H20C H 0.2982 0.6041 0.6672 0.071 Uiso 1 1 calc R U . . .
C21 C 0.2085(4) 0.7883(3) 0.72415(13) 0.0497(9) Uani 1 1 d . . . . .
H21A H 0.2987 0.8127 0.7029 0.075 Uiso 1 1 calc R U . . .
H21B H 0.2498 0.7584 0.7562 0.075 Uiso 1 1 calc R U . . .
H21C H 0.1377 0.8533 0.7308 0.075 Uiso 1 1 calc R U . . .
C22 C 0.6629(4) 0.6371(2) 0.65790(10) 0.0289(6) Uani 1 1 d . . . . .
H22 H 0.5545 0.6190 0.6435 0.035 Uiso 1 1 calc R U . . .
C23 C 0.7029(5) 0.5452(3) 0.69623(11) 0.0444(9) Uani 1 1 d . . . . .
H23A H 0.7171 0.4723 0.6788 0.067 Uiso 1 1 calc R U . . .
H23B H 0.6149 0.5387 0.7207 0.067 Uiso 1 1 calc R U . . .
H23C H 0.8026 0.5652 0.7139 0.067 Uiso 1 1 calc R U . . .
C24 C 0.6527(4) 0.7537(3) 0.68121(10) 0.0336(7) Uani 1 1 d . . . . .
H24A H 0.7594 0.7768 0.6932 0.050 Uiso 1 1 calc R U . . .
H24B H 0.5775 0.7521 0.7097 0.050 Uiso 1 1 calc R U . . .
H24C H 0.6145 0.8083 0.6559 0.050 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C10 1.361(3) . ?
F2 C16 1.365(3) . ?
N1 C2 1.486(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
O1 C1 1.199(3) . ?
O2 C1 1.330(3) . ?
O2 C4 1.469(3) . ?
O3 C19 1.433(4) . ?
O3 H3 0.8400 . ?
O4 C22 1.437(3) . ?
O4 H4 0.8400 . ?
C1 C2 1.522(3) . ?
C2 C3 1.529(3) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.510(3) . ?
C4 C6 1.533(3) . ?
C4 H4A 1.0000 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.518(3) . ?
C6 C13 1.529(3) . ?
C6 H6 1.0000 . ?
C7 C8 1.393(3) . ?
C7 C12 1.394(3) . ?
C8 C9 1.385(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.371(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(4) . ?
C11 C12 1.391(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 C18 1.393(3) . ?
C14 C15 1.397(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.366(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.370(4) . ?
C17 C18 1.396(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C21 1.471(5) . ?
C19 C20 1.491(5) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C24 1.505(4) . ?
C22 C23 1.519(4) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 O2 C4 117.75(18) . . ?
C19 O3 H3 109.5 . . ?
C22 O4 H4 109.5 . . ?
O1 C1 O2 126.1(2) . . ?
O1 C1 C2 124.2(2) . . ?
O2 C1 C2 109.65(19) . . ?
N1 C2 C1 108.21(18) . . ?
N1 C2 C3 110.35(19) . . ?
C1 C2 C3 110.0(2) . . ?
N1 C2 H2 109.4 . . ?
C1 C2 H2 109.4 . . ?
C3 C2 H2 109.4 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C4 C5 108.19(19) . . ?
O2 C4 C6 104.94(18) . . ?
C5 C4 C6 113.5(2) . . ?
O2 C4 H4A 110.0 . . ?
C5 C4 H4A 110.0 . . ?
C6 C4 H4A 110.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C13 111.77(19) . . ?
C7 C6 C4 112.11(18) . . ?
C13 C6 C4 112.28(19) . . ?
C7 C6 H6 106.7 . . ?
C13 C6 H6 106.7 . . ?
C4 C6 H6 106.7 . . ?
C8 C7 C12 118.4(2) . . ?
C8 C7 C6 119.6(2) . . ?
C12 C7 C6 122.0(2) . . ?
C9 C8 C7 121.2(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 118.5(2) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
F1 C10 C9 118.9(2) . . ?
F1 C10 C11 118.6(2) . . ?
C9 C10 C11 122.5(2) . . ?
C10 C11 C12 118.5(2) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C11 C12 C7 120.9(2) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C14 C13 C18 118.7(2) . . ?
C14 C13 C6 122.1(2) . . ?
C18 C13 C6 119.2(2) . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 118.5(2) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
F2 C16 C15 118.7(2) . . ?
F2 C16 C17 118.2(2) . . ?
C15 C16 C17 123.2(2) . . ?
C16 C17 C18 117.9(2) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
C13 C18 C17 121.2(2) . . ?
C13 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
O3 C19 C21 111.9(3) . . ?
O3 C19 C20 110.3(3) . . ?
C21 C19 C20 114.7(3) . . ?
O3 C19 H19 106.5 . . ?
C21 C19 H19 106.5 . . ?
C20 C19 H19 106.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 C24 111.3(2) . . ?
O4 C22 C23 110.3(3) . . ?
C24 C22 C23 112.7(2) . . ?
O4 C22 H22 107.4 . . ?
C24 C22 H22 107.4 . . ?
C23 C22 H22 107.4 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.537
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.043

