# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_gor008
_database_code_depnum_ccdc_archive 'CCDC 2217267'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;A N Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2022-11-03 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-11-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H30 F3 N O4'
_chemical_formula_sum            'C25 H30 F3 N O4'
_chemical_formula_weight         465.50
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_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                   13.5849(3)
_cell_length_b                   10.6443(3)
_cell_length_c                   15.6105(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.4980(10)
_cell_angle_gamma                90
_cell_volume                     2219.52(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5166
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.96
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0921 before and 0.0606 after correction.
The Ratio of minimum to maximum transmission is 0.9115.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_unetI/netI     0.1037
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33721
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.575
_diffrn_reflns_theta_min         1.830
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                9010
_reflns_number_total             13076
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 3040 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     611
_refine_ls_number_reflns         13076
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1151
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C5A(H5A), C7A(H7A), C9A(H9A)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C22(H22A,H22B),
 C8A(H8AA,H8AB), C10A(H10C,H10D), C15A(H15C,H15D), C16A(H16C,H16D), C22A(H22C,
 H22D)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C18(H18), C19(H19), C1A(H1A), C2A(H2A), C18A(H18A), C19A(H19A)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C17A(H17D,H17E,H17F), C23A(H23D,H23E,H23F), C24A(H24D,H24E,H24F),
 C25A(H25D,H25E,H25F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
C1 C 1.0169(2) 0.7317(3) 0.0216(2) 0.0188(7) Uani 1 1 d . . . . .
H1 H 1.0474 0.8013 -0.0013 0.023 Uiso 1 1 calc R U . . .
C2 C 1.0711(2) 0.6641(3) 0.0913(2) 0.0184(7) Uani 1 1 d . . . . .
H2 H 1.1394 0.6843 0.1118 0.022 Uiso 1 1 calc R U . . .
C3 C 1.0268(2) 0.5671(3) 0.1315(2) 0.0168(7) Uani 1 1 d . . . . .
C4 C 0.9286(2) 0.5361(3) 0.0948(2) 0.0165(7) Uani 1 1 d . . . . .
C5 C 0.7651(2) 0.4718(3) 0.0789(2) 0.0173(7) Uani 1 1 d . . . . .
H5 H 0.7374 0.3870 0.0605 0.021 Uiso 1 1 calc R U . . .
C6 C 0.6913(2) 0.5417(3) 0.1268(2) 0.0162(7) Uani 1 1 d . . . . .
C7 C 0.5904(2) 0.5418(3) 0.0575(2) 0.0169(7) Uani 1 1 d . . . . .
H7 H 0.5853 0.4567 0.0300 0.020 Uiso 1 1 calc R U . . .
C8 C 0.6005(2) 0.6364(3) -0.0161(2) 0.0165(7) Uani 1 1 d . . . . .
H8A H 0.5742 0.5983 -0.0736 0.020 Uiso 1 1 calc R U . . .
H8B H 0.5611 0.7130 -0.0099 0.020 Uiso 1 1 calc R U . . .
C9 C 0.7357(2) 0.7420(3) -0.0901(2) 0.0169(7) Uani 1 1 d . . . . .
H9 H 0.6941 0.8201 -0.0972 0.020 Uiso 1 1 calc R U . . .
C10 C 0.8485(2) 0.7827(3) -0.0765(2) 0.0188(7) Uani 1 1 d . . . . .
H10A H 0.8700 0.7832 -0.1338 0.023 Uiso 1 1 calc R U . . .
H10B H 0.8545 0.8696 -0.0536 0.023 Uiso 1 1 calc R U . . .
C11 C 0.9191(2) 0.6991(3) -0.0149(2) 0.0174(7) Uani 1 1 d . . . . .
C12 C 0.8817(2) 0.5937(3) 0.0194(2) 0.0151(7) Uani 1 1 d . . . . .
C13 C 0.7755(2) 0.5493(3) -0.0027(2) 0.0159(7) Uani 1 1 d . . . . .
C14 C 0.7123(2) 0.6709(3) -0.0100(2) 0.0156(7) Uani 1 1 d . . . . .
C15 C 0.7528(3) 0.4712(4) -0.0863(2) 0.0197(7) Uani 1 1 d . . . . .
H15A H 0.7997 0.3994 -0.0817 0.024 Uiso 1 1 calc R U . . .
H15B H 0.6840 0.4372 -0.0931 0.024 Uiso 1 1 calc R U . . .
C16 C 0.7623(3) 0.5493(4) -0.1664(2) 0.0227(8) Uani 1 1 d . . . . .
H16A H 0.8334 0.5712 -0.1649 0.027 Uiso 1 1 calc R U . . .
H16B H 0.7384 0.4998 -0.2198 0.027 Uiso 1 1 calc R U . . .
C17 C 0.6994(3) 0.7333(4) -0.2486(2) 0.0254(8) Uani 1 1 d . . . . .
H17A H 0.6560 0.8068 -0.2485 0.038 Uiso 1 1 calc R U . . .
H17B H 0.6725 0.6792 -0.2982 0.038 Uiso 1 1 calc R U . . .
H17C H 0.7670 0.7608 -0.2535 0.038 Uiso 1 1 calc R U . . .
C18 C 0.7276(2) 0.6746(3) 0.1451(2) 0.0165(7) Uani 1 1 d . . . . .
H18 H 0.7411 0.7089 0.2023 0.020 Uiso 1 1 calc R U . . .
C19 C 0.7392(2) 0.7400(3) 0.0752(2) 0.0155(7) Uani 1 1 d . . . . .
H19 H 0.7627 0.8242 0.0787 0.019 Uiso 1 1 calc R U . . .
C20 C 0.4938(2) 0.5594(3) 0.0960(2) 0.0174(7) Uani 1 1 d . . . . .
C21 C 0.4031(2) 0.5616(4) 0.0208(2) 0.0203(7) Uani 1 1 d . . . . .
C22 C 0.4948(2) 0.6765(3) 0.1532(2) 0.0196(7) Uani 1 1 d . . . . .
H22A H 0.5520 0.6699 0.2023 0.023 Uiso 1 1 calc R U . . .
H22B H 0.5066 0.7508 0.1183 0.023 Uiso 1 1 calc R U . . .
C23 C 0.3999(3) 0.6994(4) 0.1905(2) 0.0238(8) Uani 1 1 d . . . . .
H23A H 0.3453 0.7243 0.1434 0.036 Uiso 1 1 calc R U . . .
H23B H 0.4121 0.7665 0.2341 0.036 Uiso 1 1 calc R U . . .
H23C H 0.3814 0.6222 0.2178 0.036 Uiso 1 1 calc R U . . .
C24 C 1.1714(2) 0.5372(4) 0.2410(2) 0.0234(8) Uani 1 1 d . . . . .
H24A H 1.2132 0.5198 0.1974 0.035 Uiso 1 1 calc R U . . .
H24B H 1.1951 0.4870 0.2933 0.035 Uiso 1 1 calc R U . . .
H24C H 1.1757 0.6267 0.2561 0.035 Uiso 1 1 calc R U . . .
C25 C 0.7546(3) 0.4530(4) 0.2707(2) 0.0224(8) Uani 1 1 d . . . . .
H25A H 0.7947 0.3833 0.2546 0.034 Uiso 1 1 calc R U . . .
H25B H 0.7300 0.4315 0.3241 0.034 Uiso 1 1 calc R U . . .
H25C H 0.7960 0.5288 0.2806 0.034 Uiso 1 1 calc R U . . .
F1 F 0.31681(14) 0.5364(2) 0.04734(13) 0.0255(5) Uani 1 1 d . . . . .
F2 F 0.41093(14) 0.4765(2) -0.04145(13) 0.0265(5) Uani 1 1 d . . . . .
F3 F 0.39015(14) 0.6743(2) -0.01924(13) 0.0250(5) Uani 1 1 d . . . . .
N1 N 0.7032(2) 0.6632(3) -0.16761(17) 0.0197(6) Uani 1 1 d . . . . .
O1 O 0.86644(16) 0.4579(2) 0.13108(15) 0.0190(5) Uani 1 1 d . . . . .
O2 O 1.06940(16) 0.5051(2) 0.20615(14) 0.0198(5) Uani 1 1 d . . . . .
O3 O 0.67145(16) 0.4754(2) 0.20176(14) 0.0205(5) Uani 1 1 d . . . . .
O4 O 0.47541(19) 0.4496(2) 0.14321(17) 0.0222(6) Uani 1 1 d . . . . .
H4 H 0.527(3) 0.430(5) 0.172(3) 0.050(16) Uiso 1 1 d . . . . .
C1A C 0.0481(3) 0.2766(4) 0.6921(2) 0.0246(8) Uani 1 1 d . . . . .
H1A H 0.0118 0.2003 0.6920 0.030 Uiso 1 1 calc R U . . .
C2A C 0.0590(3) 0.3543(4) 0.7638(2) 0.0252(8) Uani 1 1 d . . . . .
H2A H 0.0256 0.3334 0.8102 0.030 Uiso 1 1 calc R U . . .
C3A C 0.1176(3) 0.4628(4) 0.7703(2) 0.0219(8) Uani 1 1 d . . . . .
C4A C 0.1577(2) 0.4950(3) 0.6972(2) 0.0193(7) Uani 1 1 d . . . . .
C5A C 0.2676(2) 0.5665(3) 0.61216(19) 0.0171(7) Uani 1 1 d . . . . .
H5A H 0.2647 0.6477 0.5796 0.020 Uiso 1 1 calc R U . . .
C6A C 0.3756(2) 0.5133(3) 0.6266(2) 0.0162(7) Uani 1 1 d . . . . .
C7A C 0.3984(2) 0.5025(3) 0.5313(2) 0.0152(7) Uani 1 1 d . . . . .
H7A H 0.3717 0.5809 0.5002 0.018 Uiso 1 1 calc R U . . .
C8A C 0.3366(2) 0.3923(3) 0.4835(2) 0.0167(7) Uani 1 1 d . . . . .
H8AA H 0.3043 0.4192 0.4244 0.020 Uiso 1 1 calc R U . . .
H8AB H 0.3813 0.3206 0.4778 0.020 Uiso 1 1 calc R U . . .
C9A C 0.1768(3) 0.2611(4) 0.4880(2) 0.0229(8) Uani 1 1 d . . . . .
H9A H 0.2125 0.1850 0.4719 0.027 Uiso 1 1 calc R U . . .
C10A C 0.1025(3) 0.2174(4) 0.5476(2) 0.0264(9) Uani 1 1 d . . . . .
H10C H 0.0361 0.2028 0.5107 0.032 Uiso 1 1 calc R U . . .
H10D H 0.1262 0.1361 0.5746 0.032 Uiso 1 1 calc R U . . .
C11A C 0.0900(3) 0.3087(4) 0.6193(2) 0.0222(8) Uani 1 1 d . . . . .
C12A C 0.1366(2) 0.4236(4) 0.6227(2) 0.0191(7) Uani 1 1 d . . . . .
C13A C 0.1982(2) 0.4695(3) 0.5580(2) 0.0170(7) Uani 1 1 d . . . . .
C14A C 0.2561(3) 0.3519(3) 0.5359(2) 0.0172(7) Uani 1 1 d . . . . .
C15A C 0.1368(3) 0.5279(4) 0.4757(2) 0.0220(8) Uani 1 1 d . . . . .
H15C H 0.0959 0.5977 0.4923 0.026 Uiso 1 1 calc R U . . .
H15D H 0.1827 0.5632 0.4394 0.026 Uiso 1 1 calc R U . . .
C16A C 0.0685(3) 0.4320(4) 0.4228(2) 0.0273(9) Uani 1 1 d . . . . .
H16C H 0.0153 0.4067 0.4550 0.033 Uiso 1 1 calc R U . . .
H16D H 0.0362 0.4696 0.3667 0.033 Uiso 1 1 calc R U . . .
C17A C 0.0651(3) 0.2335(4) 0.3476(3) 0.0356(10) Uani 1 1 d . . . . .
H17D H 0.1045 0.1585 0.3400 0.053 Uiso 1 1 calc R U . . .
H17E H 0.0428 0.2739 0.2910 0.053 Uiso 1 1 calc R U . . .
H17F H 0.0067 0.2092 0.3725 0.053 Uiso 1 1 calc R U . . .
C18A C 0.3760(2) 0.3858(3) 0.6668(2) 0.0174(7) Uani 1 1 d . . . . .
H18A H 0.4170 0.3655 0.7210 0.021 Uiso 1 1 calc R U . . .
C19A C 0.3146(3) 0.3032(3) 0.6211(2) 0.0178(7) Uani 1 1 d . . . . .
H19A H 0.3080 0.2195 0.6405 0.021 Uiso 1 1 calc R U . . .
C20A C 0.5116(2) 0.4971(3) 0.5262(2) 0.0179(7) Uani 1 1 d . . . . .
C21A C 0.5223(3) 0.4878(4) 0.4293(2) 0.0216(8) Uani 1 1 d . . . . .
C22A C 0.5679(3) 0.3904(4) 0.5795(2) 0.0222(8) Uani 1 1 d . . . . .
H22C H 0.5337 0.3105 0.5600 0.027 Uiso 1 1 calc R U . . .
H22D H 0.5621 0.4027 0.6413 0.027 Uiso 1 1 calc R U . . .
C23A C 0.6790(3) 0.3759(4) 0.5751(3) 0.0339(10) Uani 1 1 d . . . . .
H23D H 0.6859 0.3515 0.5160 0.051 Uiso 1 1 calc R U . . .
H23E H 0.7087 0.3109 0.6164 0.051 Uiso 1 1 calc R U . . .
H23F H 0.7135 0.4559 0.5903 0.051 Uiso 1 1 calc R U . . .
C24A C 0.1520(3) 0.6520(4) 0.8521(2) 0.0309(9) Uani 1 1 d . . . . .
H24D H 0.0972 0.6916 0.8117 0.046 Uiso 1 1 calc R U . . .
H24E H 0.2159 0.6727 0.8349 0.046 Uiso 1 1 calc R U . . .
H24F H 0.1521 0.6830 0.9113 0.046 Uiso 1 1 calc R U . . .
C25A C 0.4372(3) 0.6381(4) 0.7578(2) 0.0259(9) Uani 1 1 d . . . . .
H25D H 0.3857 0.7035 0.7529 0.039 Uiso 1 1 calc R U . . .
H25E H 0.5009 0.6718 0.7888 0.039 Uiso 1 1 calc R U . . .
H25F H 0.4172 0.5663 0.7900 0.039 Uiso 1 1 calc R U . . .
F1A F 0.61403(16) 0.5234(2) 0.41768(14) 0.0315(5) Uani 1 1 d . . . . .
F2A F 0.45745(17) 0.5620(2) 0.37761(12) 0.0310(5) Uani 1 1 d . . . . .
F3A F 0.50846(17) 0.3714(2) 0.39701(13) 0.0285(5) Uani 1 1 d . . . . .
N1A N 0.1269(2) 0.3213(3) 0.40647(19) 0.0253(7) Uani 1 1 d . . . . .
O1A O 0.23066(17) 0.5852(2) 0.69376(14) 0.0200(5) Uani 1 1 d . . . . .
O2A O 0.1387(2) 0.5207(3) 0.85012(15) 0.0279(6) Uani 1 1 d . . . . .
O3A O 0.44844(17) 0.5983(2) 0.67224(14) 0.0198(5) Uani 1 1 d . . . . .
O4A O 0.55739(19) 0.6147(2) 0.55074(17) 0.0228(6) Uani 1 1 d . . . . .
H4A H 0.540(3) 0.637(4) 0.596(3) 0.043(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 H1 0.9500 . ?
C1 C2 1.397(5) . ?
C1 C11 1.391(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.400(5) . ?
C3 C4 1.392(4) . ?
C3 O2 1.372(4) . ?
C4 C12 1.376(4) . ?
C4 O1 1.379(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.546(4) . ?
C5 C13 1.546(4) . ?
C5 O1 1.474(4) . ?
C6 C7 1.584(4) . ?
C6 C18 1.508(5) . ?
C6 O3 1.433(4) . ?
C7 H7 1.0000 . ?
C7 C8 1.553(4) . ?
C7 C20 1.551(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.549(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.570(4) . ?
C9 C14 1.543(4) . ?
C9 N1 1.472(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.515(5) . ?
C11 C12 1.380(5) . ?
C12 C13 1.497(4) . ?
C13 C14 1.545(5) . ?
C13 C15 1.530(4) . ?
C14 C19 1.506(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.526(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 N1 1.453(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 N1 1.460(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.328(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.540(4) . ?
C20 C22 1.532(5) . ?
C20 O4 1.427(4) . ?
C21 F1 1.339(4) . ?
C21 F2 1.347(4) . ?
C21 F3 1.349(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.527(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 O2 1.435(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C25 O3 1.431(4) . ?
O4 H4 0.79(5) . ?
C1A H1A 0.9500 . ?
C1A C2A 1.378(5) . ?
C1A C11A 1.403(5) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.396(5) . ?
C3A C4A 1.394(5) . ?
C3A O2A 1.372(4) . ?
C4A C12A 1.376(5) . ?
C4A O1A 1.388(4) . ?
C5A H5A 1.0000 . ?
C5A C6A 1.551(4) . ?
C5A C13A 1.541(5) . ?
C5A O1A 1.465(4) . ?
C6A C7A 1.578(4) . ?
C6A C18A 1.495(5) . ?
C6A O3A 1.431(4) . ?
C7A H7A 1.0000 . ?
C7A C8A 1.551(5) . ?
C7A C20A 1.555(4) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C14A 1.542(4) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.563(5) . ?
C9A C14A 1.536(5) . ?
C9A N1A 1.475(5) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A C11A 1.515(5) . ?
C11A C12A 1.374(5) . ?
C12A C13A 1.505(4) . ?
C13A C14A 1.550(5) . ?
C13A C15A 1.531(4) . ?
C14A C19A 1.511(5) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C15A C16A 1.518(5) . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C16A N1A 1.469(5) . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C17A N1A 1.463(5) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.328(5) . ?
C19A H19A 0.9500 . ?
C20A C21A 1.549(5) . ?
C20A C22A 1.529(5) . ?
C20A O4A 1.419(4) . ?
C21A F1A 1.346(4) . ?
C21A F2A 1.338(4) . ?
C21A F3A 1.338(4) . ?
C22A H22C 0.9900 . ?
C22A H22D 0.9900 . ?
C22A C23A 1.531(5) . ?
C23A H23D 0.9800 . ?
C23A H23E 0.9800 . ?
C23A H23F 0.9800 . ?
C24A H24D 0.9800 . ?
C24A H24E 0.9800 . ?
C24A H24F 0.9800 . ?
C24A O2A 1.409(4) . ?
C25A H25D 0.9800 . ?
C25A H25E 0.9800 . ?
C25A H25F 0.9800 . ?
C25A O3A 1.436(4) . ?
O4A H4A 0.82(4) . ?

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 C1 H1 119.4 . . ?
C11 C1 H1 119.4 . . ?
C11 C1 C2 121.3(3) . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.4(3) . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 116.6(3) . . ?
O2 C3 C2 125.9(3) . . ?
O2 C3 C4 117.4(3) . . ?
C12 C4 C3 120.4(3) . . ?
C12 C4 O1 113.4(3) . . ?
O1 C4 C3 125.9(3) . . ?
C6 C5 H5 109.4 . . ?
C6 C5 C13 107.9(3) . . ?
C13 C5 H5 109.4 . . ?
O1 C5 H5 109.4 . . ?
O1 C5 C6 113.8(3) . . ?
O1 C5 C13 107.0(2) . . ?
C5 C6 C7 103.1(2) . . ?
C18 C6 C5 109.0(3) . . ?
C18 C6 C7 109.9(3) . . ?
O3 C6 C5 113.1(3) . . ?
O3 C6 C7 106.8(2) . . ?
O3 C6 C18 114.3(3) . . ?
C6 C7 H7 106.1 . . ?
C8 C7 C6 108.9(3) . . ?
C8 C7 H7 106.1 . . ?
C20 C7 C6 115.1(3) . . ?
C20 C7 H7 106.1 . . ?
C20 C7 C8 113.8(3) . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C14 C8 C7 109.0(3) . . ?
C14 C8 H8A 109.9 . . ?
C14 C8 H8B 109.9 . . ?
C10 C9 H9 107.7 . . ?
C14 C9 H9 107.7 . . ?
C14 C9 C10 111.4(3) . . ?
N1 C9 H9 107.7 . . ?
N1 C9 C10 114.0(3) . . ?
N1 C9 C14 108.2(3) . . ?
C9 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 C9 114.4(3) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C1 C11 C10 124.0(3) . . ?
C12 C11 C1 115.8(3) . . ?
C12 C11 C10 119.3(3) . . ?
C4 C12 C11 123.3(3) . . ?
C4 C12 C13 109.5(3) . . ?
C11 C12 C13 125.0(3) . . ?
C12 C13 C5 102.0(3) . . ?
C12 C13 C14 104.6(3) . . ?
C12 C13 C15 113.8(3) . . ?
C14 C13 C5 112.0(3) . . ?
C15 C13 C5 112.2(3) . . ?
C15 C13 C14 111.7(3) . . ?
C9 C14 C8 114.3(3) . . ?
C9 C14 C13 106.1(3) . . ?
C13 C14 C8 109.4(3) . . ?
C19 C14 C8 104.3(3) . . ?
C19 C14 C9 115.0(3) . . ?
C19 C14 C13 107.6(3) . . ?
C13 C15 H15A 109.3 . . ?
C13 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C13 111.6(3) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
N1 C16 C15 109.7(3) . . ?
N1 C16 H16A 109.7 . . ?
N1 C16 H16B 109.7 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
C6 C18 H18 122.6 . . ?
C19 C18 C6 114.8(3) . . ?
C19 C18 H18 122.6 . . ?
C14 C19 H19 122.5 . . ?
C18 C19 C14 115.1(3) . . ?
C18 C19 H19 122.5 . . ?
C21 C20 C7 108.9(3) . . ?
C22 C20 C7 114.0(3) . . ?
C22 C20 C21 110.6(3) . . ?
O4 C20 C7 110.0(3) . . ?
O4 C20 C21 102.4(3) . . ?
O4 C20 C22 110.4(3) . . ?
F1 C21 C20 112.7(3) . . ?
F1 C21 F2 106.1(3) . . ?
F1 C21 F3 105.9(3) . . ?
F2 C21 C20 112.5(3) . . ?
F2 C21 F3 106.5(3) . . ?
F3 C21 C20 112.6(3) . . ?
C20 C22 H22A 108.4 . . ?
C20 C22 H22B 108.4 . . ?
H22A C22 H22B 107.4 . . ?
C23 C22 C20 115.7(3) . . ?
C23 C22 H22A 108.4 . . ?
C23 C22 H22B 108.4 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
C16 N1 C9 112.5(3) . . ?
C16 N1 C17 111.7(3) . . ?
C17 N1 C9 112.3(3) . . ?
C4 O1 C5 107.0(2) . . ?
C3 O2 C24 115.8(3) . . ?
C25 O3 C6 117.1(2) . . ?
C20 O4 H4 107(4) . . ?
C2A C1A H1A 119.6 . . ?
C2A C1A C11A 120.8(4) . . ?
C11A C1A H1A 119.6 . . ?
C1A C2A H2A 118.9 . . ?
C1A C2A C3A 122.1(3) . . ?
C3A C2A H2A 118.9 . . ?
C4A C3A C2A 116.5(3) . . ?
O2A C3A C2A 117.4(3) . . ?
O2A C3A C4A 125.8(3) . . ?
C12A C4A C3A 120.3(3) . . ?
C12A C4A O1A 113.0(3) . . ?
O1A C4A C3A 126.2(3) . . ?
C6A C5A H5A 109.7 . . ?
C13A C5A H5A 109.7 . . ?
C13A C5A C6A 107.7(3) . . ?
O1A C5A H5A 109.7 . . ?
O1A C5A C6A 112.8(2) . . ?
O1A C5A C13A 107.2(3) . . ?
C5A C6A C7A 103.5(2) . . ?
C18A C6A C5A 108.8(3) . . ?
C18A C6A C7A 110.1(3) . . ?
O3A C6A C5A 113.1(3) . . ?
O3A C6A C7A 106.2(2) . . ?
O3A C6A C18A 114.5(3) . . ?
C6A C7A H7A 106.3 . . ?
C8A C7A C6A 109.1(3) . . ?
C8A C7A H7A 106.3 . . ?
C8A C7A C20A 113.7(3) . . ?
C20A C7A C6A 114.6(3) . . ?
C20A C7A H7A 106.3 . . ?
C7A C8A H8AA 109.8 . . ?
C7A C8A H8AB 109.8 . . ?
H8AA C8A H8AB 108.3 . . ?
C14A C8A C7A 109.3(3) . . ?
C14A C8A H8AA 109.8 . . ?
C14A C8A H8AB 109.8 . . ?
C10A C9A H9A 107.6 . . ?
C14A C9A H9A 107.6 . . ?
C14A C9A C10A 111.7(3) . . ?
N1A C9A H9A 107.6 . . ?
N1A C9A C10A 113.5(3) . . ?
N1A C9A C14A 108.6(3) . . ?
C9A C10A H10C 108.6 . . ?
C9A C10A H10D 108.6 . . ?
H10C C10A H10D 107.5 . . ?
C11A C10A C9A 114.8(3) . . ?
C11A C10A H10C 108.6 . . ?
C11A C10A H10D 108.6 . . ?
C1A C11A C10A 124.0(3) . . ?
C12A C11A C1A 115.9(3) . . ?
C12A C11A C10A 119.1(3) . . ?
C4A C12A C13A 109.4(3) . . ?
C11A C12A C4A 123.3(3) . . ?
C11A C12A C13A 124.9(3) . . ?
C5A C13A C14A 112.2(3) . . ?
C12A C13A C5A 102.1(3) . . ?
C12A C13A C14A 104.7(3) . . ?
C12A C13A C15A 114.2(3) . . ?
C15A C13A C5A 111.9(3) . . ?
C15A C13A C14A 111.2(3) . . ?
C8A C14A C13A 109.3(3) . . ?
C9A C14A C8A 114.8(3) . . ?
C9A C14A C13A 106.1(3) . . ?
C19A C14A C8A 104.6(3) . . ?
C19A C14A C9A 115.0(3) . . ?
C19A C14A C13A 106.8(3) . . ?
C13A C15A H15C 109.3 . . ?
C13A C15A H15D 109.3 . . ?
H15C C15A H15D 107.9 . . ?
C16A C15A C13A 111.7(3) . . ?
C16A C15A H15C 109.3 . . ?
C16A C15A H15D 109.3 . . ?
C15A C16A H16C 109.7 . . ?
C15A C16A H16D 109.7 . . ?
H16C C16A H16D 108.2 . . ?
N1A C16A C15A 109.8(3) . . ?
N1A C16A H16C 109.7 . . ?
N1A C16A H16D 109.7 . . ?
H17D C17A H17E 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
N1A C17A H17D 109.5 . . ?
N1A C17A H17E 109.5 . . ?
N1A C17A H17F 109.5 . . ?
C6A C18A H18A 122.5 . . ?
C19A C18A C6A 115.0(3) . . ?
C19A C18A H18A 122.5 . . ?
C14A C19A H19A 122.5 . . ?
C18A C19A C14A 115.1(3) . . ?
C18A C19A H19A 122.5 . . ?
C21A C20A C7A 108.8(3) . . ?
C22A C20A C7A 113.6(3) . . ?
C22A C20A C21A 110.9(3) . . ?
O4A C20A C7A 110.1(3) . . ?
O4A C20A C21A 101.8(3) . . ?
O4A C20A C22A 110.9(3) . . ?
F1A C21A C20A 111.5(3) . . ?
F2A C21A C20A 112.5(3) . . ?
F2A C21A F1A 106.1(3) . . ?
F3A C21A C20A 113.3(3) . . ?
F3A C21A F1A 106.2(3) . . ?
F3A C21A F2A 106.7(3) . . ?
C20A C22A H22C 108.1 . . ?
C20A C22A H22D 108.1 . . ?
C20A C22A C23A 116.8(3) . . ?
H22C C22A H22D 107.3 . . ?
C23A C22A H22C 108.1 . . ?
C23A C22A H22D 108.1 . . ?
C22A C23A H23D 109.5 . . ?
C22A C23A H23E 109.5 . . ?
C22A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
H24D C24A H24E 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
O2A C24A H24D 109.5 . . ?
O2A C24A H24E 109.5 . . ?
O2A C24A H24F 109.5 . . ?
H25D C25A H25E 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 109.5 . . ?
O3A C25A H25D 109.5 . . ?
O3A C25A H25E 109.5 . . ?
O3A C25A H25F 109.5 . . ?
C16A N1A C9A 112.1(3) . . ?
C17A N1A C9A 112.7(3) . . ?
C17A N1A C16A 110.8(3) . . ?
C4A O1A C5A 107.4(2) . . ?
C3A O2A C24A 118.0(3) . . ?
C6A O3A C25A 118.0(3) . . ?
C20A O4A H4A 108(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 4.3(5) . . . . ?
C1 C2 C3 O2 -172.0(3) . . . . ?
C1 C11 C12 C4 11.6(5) . . . . ?
C1 C11 C12 C13 172.9(3) . . . . ?
C2 C1 C11 C10 166.3(3) . . . . ?
C2 C1 C11 C12 -2.8(5) . . . . ?
C2 C3 C4 C12 4.2(5) . . . . ?
C2 C3 C4 O1 -169.6(3) . . . . ?
C2 C3 O2 C24 -5.2(5) . . . . ?
C3 C4 C12 C11 -12.7(5) . . . . ?
C3 C4 C12 C13 -176.5(3) . . . . ?
C3 C4 O1 C5 169.1(3) . . . . ?
C4 C3 O2 C24 178.5(3) . . . . ?
C4 C12 C13 C5 7.7(4) . . . . ?
C4 C12 C13 C14 124.4(3) . . . . ?
C4 C12 C13 C15 -113.4(3) . . . . ?
C5 C6 C7 C8 -72.8(3) . . . . ?
C5 C6 C7 C20 158.0(3) . . . . ?
C5 C6 C18 C19 57.1(4) . . . . ?
C5 C6 O3 C25 61.8(4) . . . . ?
C5 C13 C14 C8 -60.1(3) . . . . ?
C5 C13 C14 C9 176.2(3) . . . . ?
C5 C13 C14 C19 52.6(3) . . . . ?
C5 C13 C15 C16 179.4(3) . . . . ?
C6 C5 C13 C12 112.4(3) . . . . ?
C6 C5 C13 C14 1.1(4) . . . . ?
C6 C5 C13 C15 -125.4(3) . . . . ?
C6 C5 O1 C4 -109.3(3) . . . . ?
C6 C7 C8 C14 14.9(4) . . . . ?
C6 C7 C20 C21 178.2(3) . . . . ?
C6 C7 C20 C22 54.2(4) . . . . ?
C6 C7 C20 O4 -70.4(4) . . . . ?
C6 C18 C19 C14 1.1(4) . . . . ?
C7 C6 C18 C19 -55.2(4) . . . . ?
C7 C6 O3 C25 174.5(3) . . . . ?
C7 C8 C14 C9 167.9(3) . . . . ?
C7 C8 C14 C13 49.2(3) . . . . ?
C7 C8 C14 C19 -65.6(3) . . . . ?
C7 C20 C21 F1 160.1(3) . . . . ?
C7 C20 C21 F2 40.2(4) . . . . ?
C7 C20 C21 F3 -80.2(4) . . . . ?
C7 C20 C22 C23 178.4(3) . . . . ?
C8 C7 C20 C21 51.6(4) . . . . ?
C8 C7 C20 C22 -72.4(4) . . . . ?
C8 C7 C20 O4 163.0(3) . . . . ?
C8 C14 C19 C18 59.9(4) . . . . ?
C9 C10 C11 C1 -165.1(3) . . . . ?
C9 C10 C11 C12 3.5(4) . . . . ?
C9 C14 C19 C18 -174.2(3) . . . . ?
C10 C9 C14 C8 175.7(3) . . . . ?
C10 C9 C14 C13 -63.7(3) . . . . ?
C10 C9 C14 C19 55.1(4) . . . . ?
C10 C9 N1 C16 57.7(4) . . . . ?
C10 C9 N1 C17 -69.4(4) . . . . ?
C10 C11 C12 C4 -158.0(3) . . . . ?
C10 C11 C12 C13 3.4(5) . . . . ?
C11 C1 C2 C3 -5.0(5) . . . . ?
C11 C12 C13 C5 -155.8(3) . . . . ?
C11 C12 C13 C14 -39.1(4) . . . . ?
C11 C12 C13 C15 83.1(4) . . . . ?
C12 C4 O1 C5 -5.1(4) . . . . ?
C12 C13 C14 C8 -169.7(2) . . . . ?
C12 C13 C14 C9 66.6(3) . . . . ?
C12 C13 C14 C19 -57.0(3) . . . . ?
C12 C13 C15 C16 -65.4(4) . . . . ?
C13 C5 C6 C7 62.0(3) . . . . ?
C13 C5 C6 C18 -54.7(3) . . . . ?
C13 C5 C6 O3 177.0(3) . . . . ?
C13 C5 O1 C4 9.8(3) . . . . ?
C13 C14 C19 C18 -56.2(4) . . . . ?
C13 C15 C16 N1 -51.8(4) . . . . ?
C14 C9 C10 C11 27.4(4) . . . . ?
C14 C9 N1 C16 -66.8(3) . . . . ?
C14 C9 N1 C17 166.1(3) . . . . ?
C14 C13 C15 C16 52.7(4) . . . . ?
C15 C13 C14 C8 66.7(3) . . . . ?
C15 C13 C14 C9 -56.9(3) . . . . ?
C15 C13 C14 C19 179.4(3) . . . . ?
C15 C16 N1 C9 60.0(4) . . . . ?
C15 C16 N1 C17 -172.6(3) . . . . ?
C18 C6 C7 C8 43.2(4) . . . . ?
C18 C6 C7 C20 -85.9(3) . . . . ?
C18 C6 O3 C25 -63.7(4) . . . . ?
C20 C7 C8 C14 144.7(3) . . . . ?
C21 C20 C22 C23 55.4(4) . . . . ?
C22 C20 C21 F1 -74.0(4) . . . . ?
C22 C20 C21 F2 166.1(3) . . . . ?
C22 C20 C21 F3 45.8(4) . . . . ?
N1 C9 C10 C11 -95.4(3) . . . . ?
N1 C9 C14 C8 -58.2(4) . . . . ?
N1 C9 C14 C13 62.4(3) . . . . ?
N1 C9 C14 C19 -178.8(3) . . . . ?
O1 C4 C12 C11 161.8(3) . . . . ?
O1 C4 C12 C13 -2.0(4) . . . . ?
O1 C5 C6 C7 -179.4(3) . . . . ?
O1 C5 C6 C18 63.9(3) . . . . ?
O1 C5 C6 O3 -64.4(4) . . . . ?
O1 C5 C13 C12 -10.4(3) . . . . ?
O1 C5 C13 C14 -121.7(3) . . . . ?
O1 C5 C13 C15 111.8(3) . . . . ?
O2 C3 C4 C12 -179.2(3) . . . . ?
O2 C3 C4 O1 7.0(5) . . . . ?
O3 C6 C7 C8 167.7(3) . . . . ?
O3 C6 C7 C20 38.6(4) . . . . ?
O3 C6 C18 C19 -175.3(3) . . . . ?
O4 C20 C21 F1 43.7(4) . . . . ?
O4 C20 C21 F2 -76.2(3) . . . . ?
O4 C20 C21 F3 163.4(3) . . . . ?
O4 C20 C22 C23 -57.2(4) . . . . ?
C1A C2A C3A C4A 5.5(5) . . . . ?
C1A C2A C3A O2A -168.2(3) . . . . ?
C1A C11A C12A C4A 11.1(5) . . . . ?
C1A C11A C12A C13A 171.3(3) . . . . ?
C2A C1A C11A C10A 165.3(4) . . . . ?
C2A C1A C11A C12A -3.4(5) . . . . ?
C2A C3A C4A C12A 1.9(5) . . . . ?
C2A C3A C4A O1A -168.5(3) . . . . ?
C2A C3A O2A C24A -149.5(4) . . . . ?
C3A C4A C12A C11A -10.6(5) . . . . ?
C3A C4A C12A C13A -173.5(3) . . . . ?
C3A C4A O1A C5A 166.3(3) . . . . ?
C4A C3A O2A C24A 37.5(5) . . . . ?
C4A C12A C13A C5A 7.2(4) . . . . ?
C4A C12A C13A C14A 124.3(3) . . . . ?
C4A C12A C13A C15A -113.8(3) . . . . ?
C5A C6A C7A C8A -71.9(3) . . . . ?
C5A C6A C7A C20A 159.4(3) . . . . ?
C5A C6A C18A C19A 57.8(4) . . . . ?
C5A C6A O3A C25A 59.3(4) . . . . ?
C5A C13A C14A C8A -59.5(3) . . . . ?
C5A C13A C14A C9A 176.2(3) . . . . ?
C5A C13A C14A C19A 53.1(3) . . . . ?
C5A C13A C15A C16A -179.9(3) . . . . ?
C6A C5A C13A C12A 111.9(3) . . . . ?
C6A C5A C13A C14A 0.4(4) . . . . ?
C6A C5A C13A C15A -125.5(3) . . . . ?
C6A C5A O1A C4A -109.2(3) . . . . ?
C6A C7A C8A C14A 13.5(4) . . . . ?
C6A C7A C20A C21A -179.5(3) . . . . ?
C6A C7A C20A C22A 56.4(4) . . . . ?
C6A C7A C20A O4A -68.7(4) . . . . ?
C6A C18A C19A C14A 0.7(4) . . . . ?
C7A C6A C18A C19A -55.0(4) . . . . ?
C7A C6A O3A C25A 172.1(3) . . . . ?
C7A C8A C14A C9A 168.9(3) . . . . ?
C7A C8A C14A C13A 49.9(3) . . . . ?
C7A C8A C14A C19A -64.1(3) . . . . ?
C7A C20A C21A F1A 159.9(3) . . . . ?
C7A C20A C21A F2A 40.8(4) . . . . ?
C7A C20A C21A F3A -80.3(4) . . . . ?
C7A C20A C22A C23A 177.8(3) . . . . ?
C8A C7A C20A C21A 54.2(4) . . . . ?
C8A C7A C20A C22A -70.0(4) . . . . ?
C8A C7A C20A O4A 164.9(3) . . . . ?
C8A C14A C19A C18A 59.6(4) . . . . ?
C9A C10A C11A C1A -163.4(3) . . . . ?
C9A C10A C11A C12A 5.0(5) . . . . ?
C9A C14A C19A C18A -173.5(3) . . . . ?
C10A C9A C14A C8A 176.0(3) . . . . ?
C10A C9A C14A C13A -63.2(4) . . . . ?
C10A C9A C14A C19A 54.6(4) . . . . ?
C10A C9A N1A C16A 58.7(4) . . . . ?
C10A C9A N1A C17A -67.1(4) . . . . ?
C10A C11A C12A C4A -158.2(3) . . . . ?
C10A C11A C12A C13A 2.0(5) . . . . ?
C11A C1A C2A C3A -4.8(6) . . . . ?
C11A C12A C13A C5A -155.3(3) . . . . ?
C11A C12A C13A C14A -38.2(4) . . . . ?
C11A C12A C13A C15A 83.6(4) . . . . ?
C12A C4A O1A C5A -4.7(4) . . . . ?
C12A C13A C14A C8A -169.4(3) . . . . ?
C12A C13A C14A C9A 66.2(3) . . . . ?
C12A C13A C14A C19A -56.9(3) . . . . ?
C12A C13A C15A C16A -64.5(4) . . . . ?
C13A C5A C6A C7A 62.3(3) . . . . ?
C13A C5A C6A C18A -54.8(3) . . . . ?
C13A C5A C6A O3A 176.7(2) . . . . ?
C13A C5A O1A C4A 9.2(3) . . . . ?
C13A C14A C19A C18A -56.2(4) . . . . ?
C13A C15A C16A N1A -52.4(4) . . . . ?
C14A C9A C10A C11A 26.4(5) . . . . ?
C14A C9A N1A C16A -66.1(4) . . . . ?
C14A C9A N1A C17A 168.1(3) . . . . ?
C14A C13A C15A C16A 53.7(4) . . . . ?
C15A C13A C14A C8A 66.8(3) . . . . ?
C15A C13A C14A C9A -57.6(3) . . . . ?
C15A C13A C14A C19A 179.4(3) . . . . ?
C15A C16A N1A C9A 59.4(4) . . . . ?
C15A C16A N1A C17A -173.8(3) . . . . ?
C18A C6A C7A C8A 44.2(3) . . . . ?
C18A C6A C7A C20A -84.5(3) . . . . ?
C18A C6A O3A C25A -66.2(4) . . . . ?
C20A C7A C8A C14A 142.7(3) . . . . ?
C21A C20A C22A C23A 54.9(4) . . . . ?
C22A C20A C21A F1A -74.4(4) . . . . ?
C22A C20A C21A F2A 166.5(3) . . . . ?
C22A C20A C21A F3A 45.4(4) . . . . ?
N1A C9A C10A C11A -96.6(4) . . . . ?
N1A C9A C14A C8A -58.2(4) . . . . ?
N1A C9A C14A C13A 62.6(3) . . . . ?
N1A C9A C14A C19A -179.6(3) . . . . ?
O1A C4A C12A C11A 161.0(3) . . . . ?
O1A C4A C12A C13A -1.9(4) . . . . ?
O1A C5A C6A C7A -179.6(3) . . . . ?
O1A C5A C6A C18A 63.4(3) . . . . ?
O1A C5A C6A O3A -65.1(4) . . . . ?
O1A C5A C13A C12A -9.8(3) . . . . ?
O1A C5A C13A C14A -121.3(3) . . . . ?
O1A C5A C13A C15A 112.8(3) . . . . ?
O2A C3A C4A C12A 175.0(3) . . . . ?
O2A C3A C4A O1A 4.6(6) . . . . ?
O3A C6A C7A C8A 168.8(3) . . . . ?
O3A C6A C7A C20A 40.1(4) . . . . ?
O3A C6A C18A C19A -174.6(3) . . . . ?
O4A C20A C21A F1A 43.7(4) . . . . ?
O4A C20A C21A F2A -75.4(3) . . . . ?
O4A C20A C21A F3A 163.5(3) . . . . ?
O4A C20A C22A C23A -57.6(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2221023'
loop_
_audit_author_name
_audit_author_address
'Alexander F. Smolyakov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-11-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H28 F3 N O4'
_chemical_formula_sum            'C24 H28 F3 N O4'
_chemical_formula_weight         451.47
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
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                   9.0266(17)
_cell_length_b                   11.611(2)
_cell_length_c                   20.467(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2145.1(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6748
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1297 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.9047.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
_exptl_crystal_recrystallization_method 'crystallized from ???'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16410
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.027
_diffrn_reflns_theta_min         1.990
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                5251
_reflns_number_total             6255
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 1895 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         6255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.1617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1003
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C5(H5)
1.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C16(H16A,H16B), C15(H15A,H15B)
1.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C1(H1), C2(H2)
1.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.12176(18) 0.18915(13) 0.35861(6) 0.0253(4) Uani 1 1 d . . . . .
O3 O 0.13112(19) 0.60857(14) 0.41353(7) 0.0187(4) Uani 1 1 d . . . . .
F2 F -0.02866(17) 0.23144(13) 0.43610(7) 0.0266(4) Uani 1 1 d . . . . .
O2 O 0.07067(19) 0.74114(14) 0.53857(8) 0.0186(4) Uani 1 1 d . . . . .
O1 O 0.1772(2) 0.95527(14) 0.58592(8) 0.0259(4) Uani 1 1 d . . . . .
O4 O 0.08396(19) 0.40877(17) 0.35724(7) 0.0193(4) Uani 1 1 d . . . . .
F3 F 0.19382(18) 0.17755(12) 0.45765(6) 0.0259(3) Uani 1 1 d . . . . .
C7 C 0.1067(2) 0.43306(19) 0.47549(9) 0.0132(4) Uani 1 1 d . . . . .
H7 H -0.0040 0.4322 0.4738 0.016 Uiso 1 1 calc R . . . .
C13 C 0.0790(2) 0.55876(19) 0.59523(10) 0.0142(4) Uani 1 1 d . . . . .
C14 C 0.2013(3) 0.46571(19) 0.58977(9) 0.0135(4) Uani 1 1 d . . . . .
C8 C 0.1511(3) 0.37333(19) 0.54066(10) 0.0137(4) Uani 1 1 d . . . . .
H8A H 0.0655 0.3303 0.5585 0.016 Uiso 1 1 calc R . . . .
H8B H 0.2327 0.3181 0.5327 0.016 Uiso 1 1 calc R . . . .
C18 C 0.3110(3) 0.5722(2) 0.50195(10) 0.0153(4) Uani 1 1 d . . . . .
H18 H 0.3868 0.6105 0.4782 0.018 Uiso 1 1 calc R . . . .
C3 C 0.1995(3) 0.8567(2) 0.62147(10) 0.0186(5) Uani 1 1 d . . . . .
N17 N 0.0910(2) 0.36679(18) 0.68341(9) 0.0202(4) Uani 1 1 d . . . . .
C20 C 0.1615(3) 0.3679(2) 0.41328(10) 0.0148(4) Uani 1 1 d . . . . .
C6 C 0.1542(3) 0.56349(19) 0.47778(9) 0.0140(4) Uani 1 1 d . . . . .
C10 C 0.2876(3) 0.5201(2) 0.70538(11) 0.0198(5) Uani 1 1 d . . . . .
H10A H 0.2505 0.5066 0.7502 0.024 Uiso 1 1 calc R . . . .
H10B H 0.3971 0.5150 0.7068 0.024 Uiso 1 1 calc R . . . .
C11 C 0.2452(3) 0.6411(2) 0.68506(10) 0.0170(5) Uani 1 1 d . . . . .
C9 C 0.2279(3) 0.4215(2) 0.66005(10) 0.0164(5) Uani 1 1 d . . . . .
H9 H 0.3060 0.3606 0.6578 0.020 Uiso 1 1 calc R . . . .
C5 C 0.0482(3) 0.6171(2) 0.52893(10) 0.0151(4) Uani 1 1 d . . . . .
H5 H -0.0568 0.6024 0.5157 0.018 Uiso 1 1 calc R . . . .
C19 C 0.3350(3) 0.52192(19) 0.55924(10) 0.0153(4) Uani 1 1 d . . . . .
H19 H 0.4296 0.5214 0.5795 0.018 Uiso 1 1 calc R . . . .
C16 C -0.0287(3) 0.4504(2) 0.69146(11) 0.0221(5) Uani 1 1 d . . . . .
H16A H 0.0000 0.5083 0.7246 0.026 Uiso 1 1 calc R . . . .
H16B H -0.1190 0.4106 0.7071 0.026 Uiso 1 1 calc R . . . .
C12 C 0.1487(3) 0.6545(2) 0.63290(10) 0.0154(4) Uani 1 1 d . . . . .
C21 C 0.1121(3) 0.2420(2) 0.41679(10) 0.0184(5) Uani 1 1 d . . . . .
C1 C 0.3120(3) 0.7412(2) 0.70804(10) 0.0193(5) Uani 1 1 d . . . . .
H1 H 0.3766 0.7372 0.7446 0.023 Uiso 1 1 calc R . . . .
C2 C 0.2857(3) 0.8478(2) 0.67815(11) 0.0201(5) Uani 1 1 d . . . . .
H2 H 0.3273 0.9155 0.6967 0.024 Uiso 1 1 calc R . . . .
C4 C 0.1372(3) 0.7559(2) 0.59867(10) 0.0173(5) Uani 1 1 d . . . . .
C15 C -0.0616(3) 0.5105(2) 0.62685(11) 0.0192(5) Uani 1 1 d . . . . .
H15A H -0.1324 0.5741 0.6345 0.023 Uiso 1 1 calc R . . . .
H15B H -0.1087 0.4550 0.5965 0.023 Uiso 1 1 calc R . . . .
C22 C 0.3278(3) 0.3720(2) 0.40150(11) 0.0203(5) Uani 1 1 d . . . . .
H22A H 0.3532 0.3216 0.3648 0.031 Uiso 1 1 calc GR . . . .
H22B H 0.3799 0.3459 0.4408 0.031 Uiso 1 1 calc GR . . . .
H22C H 0.3575 0.4512 0.3913 0.031 Uiso 1 1 calc GR . . . .
C23 C 0.1122(3) 0.3001(2) 0.74311(11) 0.0264(6) Uani 1 1 d . . . . .
H23A H 0.0212 0.2577 0.7532 0.040 Uiso 1 1 calc GR . . . .
H23B H 0.1358 0.3523 0.7793 0.040 Uiso 1 1 calc GR . . . .
H23C H 0.1939 0.2456 0.7369 0.040 Uiso 1 1 calc GR . . . .
C24 C 0.2037(3) 1.0622(2) 0.61821(12) 0.0236(5) Uani 1 1 d . . . . .
H24A H 0.1734 1.1258 0.5897 0.035 Uiso 1 1 calc GR . . . .
H24B H 0.3094 1.0693 0.6282 0.035 Uiso 1 1 calc GR . . . .
H24C H 0.1464 1.0649 0.6589 0.035 Uiso 1 1 calc GR . . . .
C25 C 0.1577(4) 0.7289(2) 0.40353(12) 0.0287(6) Uani 1 1 d . . . . .
H25A H 0.1629 0.7449 0.3566 0.043 Uiso 1 1 calc GR . . . .
H25B H 0.2516 0.7505 0.4242 0.043 Uiso 1 1 calc GR . . . .
H25C H 0.0769 0.7736 0.4230 0.043 Uiso 1 1 calc GR . . . .
H4 H 0.086(3) 0.476(3) 0.3607(12) 0.015(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C21 1.342(2) . ?
O3 C6 1.431(2) . ?
O3 C25 1.432(3) . ?
F2 C21 1.336(3) . ?
O2 C5 1.468(3) . ?
O2 C4 1.380(3) . ?
O1 C3 1.371(3) . ?
O1 C24 1.426(3) . ?
O4 C20 1.425(3) . ?
O4 H4 0.79(3) . ?
F3 C21 1.343(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.556(3) . ?
C7 C20 1.562(3) . ?
C7 C6 1.575(3) . ?
C13 C14 1.548(3) . ?
C13 C5 1.542(3) . ?
C13 C12 1.492(3) . ?
C13 C15 1.531(3) . ?
C14 C8 1.538(3) . ?
C14 C9 1.546(3) . ?
C14 C19 1.508(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C18 H18 0.9500 . ?
C18 C6 1.503(3) . ?
C18 C19 1.328(3) . ?
C3 C2 1.401(3) . ?
C3 C4 1.380(3) . ?
N17 C9 1.470(3) . ?
N17 C16 1.462(3) . ?
N17 C23 1.459(3) . ?
C20 C21 1.530(3) . ?
C20 C22 1.521(3) . ?
C6 C5 1.548(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.515(3) . ?
C10 C9 1.569(3) . ?
C11 C12 1.387(3) . ?
C11 C1 1.391(3) . ?
C9 H9 1.0000 . ?
C5 H5 1.0000 . ?
C19 H19 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C15 1.524(3) . ?
C12 C4 1.374(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.401(3) . ?
C2 H2 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C6 O3 C25 117.64(18) . . ?
C4 O2 C5 107.57(16) . . ?
C3 O1 C24 117.13(17) . . ?
C20 O4 H4 104.3(19) . . ?
C8 C7 H7 106.4 . . ?
C8 C7 C20 113.66(18) . . ?
C8 C7 C6 109.45(17) . . ?
C20 C7 H7 106.4 . . ?
C20 C7 C6 113.84(17) . . ?
C6 C7 H7 106.4 . . ?
C5 C13 C14 111.81(17) . . ?
C12 C13 C14 104.90(18) . . ?
C12 C13 C5 101.75(18) . . ?
C12 C13 C15 113.80(18) . . ?
C15 C13 C14 111.45(19) . . ?
C15 C13 C5 112.54(19) . . ?
C8 C14 C13 108.91(18) . . ?
C8 C14 C9 114.99(18) . . ?
C9 C14 C13 105.99(17) . . ?
C19 C14 C13 107.36(18) . . ?
C19 C14 C8 105.46(16) . . ?
C19 C14 C9 113.86(19) . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
C14 C8 C7 108.99(18) . . ?
C14 C8 H8A 109.9 . . ?
C14 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C6 C18 H18 122.7 . . ?
C19 C18 H18 122.7 . . ?
C19 C18 C6 114.5(2) . . ?
O1 C3 C2 125.6(2) . . ?
O1 C3 C4 118.0(2) . . ?
C4 C3 C2 116.3(2) . . ?
C16 N17 C9 111.78(19) . . ?
C23 N17 C9 113.1(2) . . ?
C23 N17 C16 110.79(19) . . ?
O4 C20 C7 109.82(18) . . ?
O4 C20 C21 102.28(18) . . ?
O4 C20 C22 110.28(18) . . ?
C21 C20 C7 109.41(17) . . ?
C22 C20 C7 115.24(18) . . ?
C22 C20 C21 109.0(2) . . ?
O3 C6 C7 106.56(17) . . ?
O3 C6 C18 114.52(18) . . ?
O3 C6 C5 112.62(18) . . ?
C18 C6 C7 109.32(18) . . ?
C18 C6 C5 109.40(17) . . ?
C5 C6 C7 103.79(17) . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C11 C10 C9 115.31(19) . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
C12 C11 C10 118.3(2) . . ?
C12 C11 C1 116.1(2) . . ?
C1 C11 C10 124.9(2) . . ?
C14 C9 C10 111.20(19) . . ?
C14 C9 H9 107.6 . . ?
N17 C9 C14 108.38(18) . . ?
N17 C9 C10 114.33(18) . . ?
N17 C9 H9 107.6 . . ?
C10 C9 H9 107.6 . . ?
O2 C5 C13 106.71(17) . . ?
O2 C5 C6 113.56(18) . . ?
O2 C5 H5 109.5 . . ?
C13 C5 C6 107.89(18) . . ?
C13 C5 H5 109.5 . . ?
C6 C5 H5 109.5 . . ?
C14 C19 H19 122.4 . . ?
C18 C19 C14 115.2(2) . . ?
C18 C19 H19 122.4 . . ?
N17 C16 H16A 109.6 . . ?
N17 C16 H16B 109.6 . . ?
N17 C16 C15 110.48(18) . . ?
H16A C16 H16B 108.1 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
C11 C12 C13 125.4(2) . . ?
C4 C12 C13 110.08(19) . . ?
C4 C12 C11 122.4(2) . . ?
F1 C21 F3 105.18(19) . . ?
F1 C21 C20 112.09(18) . . ?
F2 C21 F1 106.42(19) . . ?
F2 C21 F3 106.68(18) . . ?
F2 C21 C20 112.3(2) . . ?
F3 C21 C20 113.64(19) . . ?
C11 C1 H1 119.4 . . ?
C11 C1 C2 121.1(2) . . ?
C2 C1 H1 119.4 . . ?
C3 C2 H2 119.3 . . ?
C1 C2 C3 121.4(2) . . ?
C1 C2 H2 119.3 . . ?
O2 C4 C3 125.8(2) . . ?
C12 C4 O2 112.4(2) . . ?
C12 C4 C3 121.6(2) . . ?
C13 C15 H15A 109.2 . . ?
C13 C15 H15B 109.2 . . ?
C16 C15 C13 111.9(2) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N17 C23 H23A 109.5 . . ?
N17 C23 H23B 109.5 . . ?
N17 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O3 C25 H25A 109.5 . . ?
O3 C25 H25B 109.5 . . ?
O3 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C6 C5 O2 -64.1(2) . . . . ?
O3 C6 C5 C13 177.80(18) . . . . ?
O1 C3 C2 C1 -174.5(2) . . . . ?
O1 C3 C4 O2 9.3(4) . . . . ?
O1 C3 C4 C12 -177.0(2) . . . . ?
O4 C20 C21 F1 47.7(2) . . . . ?
O4 C20 C21 F2 -72.0(2) . . . . ?
O4 C20 C21 F3 166.77(17) . . . . ?
C7 C20 C21 F1 164.08(18) . . . . ?
C7 C20 C21 F2 44.4(2) . . . . ?
C7 C20 C21 F3 -76.8(2) . . . . ?
C7 C6 C5 O2 -178.98(16) . . . . ?
C7 C6 C5 C13 63.0(2) . . . . ?
C13 C14 C8 C7 53.0(2) . . . . ?
C13 C14 C9 N17 63.4(2) . . . . ?
C13 C14 C9 C10 -63.0(2) . . . . ?
C13 C14 C19 C18 -55.7(2) . . . . ?
C13 C12 C4 O2 -2.3(3) . . . . ?
C13 C12 C4 C3 -176.8(2) . . . . ?
C14 C13 C5 O2 -123.38(19) . . . . ?
C14 C13 C5 C6 -1.0(3) . . . . ?
C14 C13 C12 C11 -38.2(3) . . . . ?
C14 C13 C12 C4 125.4(2) . . . . ?
C14 C13 C15 C16 52.0(3) . . . . ?
C8 C7 C20 O4 164.16(18) . . . . ?
C8 C7 C20 C21 52.6(2) . . . . ?
C8 C7 C20 C22 -70.6(3) . . . . ?
C8 C7 C6 O3 171.41(17) . . . . ?
C8 C7 C6 C18 47.2(2) . . . . ?
C8 C7 C6 C5 -69.5(2) . . . . ?
C8 C14 C9 N17 -56.9(2) . . . . ?
C8 C14 C9 C10 176.61(19) . . . . ?
C8 C14 C19 C18 60.3(2) . . . . ?
C18 C6 C5 O2 64.4(2) . . . . ?
C18 C6 C5 C13 -53.6(2) . . . . ?
N17 C16 C15 C13 -50.9(3) . . . . ?
C20 C7 C8 C14 138.3(2) . . . . ?
C20 C7 C6 O3 43.0(2) . . . . ?
C20 C7 C6 C18 -81.3(2) . . . . ?
C20 C7 C6 C5 162.09(17) . . . . ?
C6 C7 C8 C14 9.8(2) . . . . ?
C6 C7 C20 O4 -69.6(2) . . . . ?
C6 C7 C20 C21 178.88(18) . . . . ?
C6 C7 C20 C22 55.7(3) . . . . ?
C6 C18 C19 C14 -0.2(3) . . . . ?
C10 C11 C12 C13 1.4(3) . . . . ?
C10 C11 C12 C4 -160.3(2) . . . . ?
C10 C11 C1 C2 168.0(2) . . . . ?
C11 C10 C9 C14 26.0(3) . . . . ?
C11 C10 C9 N17 -97.1(2) . . . . ?
C11 C12 C4 O2 161.9(2) . . . . ?
C11 C12 C4 C3 -12.6(4) . . . . ?
C11 C1 C2 C3 -4.4(4) . . . . ?
C9 C14 C8 C7 171.75(19) . . . . ?
C9 C14 C19 C18 -172.7(2) . . . . ?
C9 N17 C16 C15 59.1(3) . . . . ?
C9 C10 C11 C12 5.6(3) . . . . ?
C9 C10 C11 C1 -164.3(2) . . . . ?
C5 O2 C4 C3 168.4(2) . . . . ?
C5 O2 C4 C12 -5.8(3) . . . . ?
C5 C13 C14 C8 -59.7(2) . . . . ?
C5 C13 C14 C9 176.01(18) . . . . ?
C5 C13 C14 C19 54.0(2) . . . . ?
C5 C13 C12 C11 -154.8(2) . . . . ?
C5 C13 C12 C4 8.8(2) . . . . ?
C5 C13 C15 C16 178.51(19) . . . . ?
C19 C14 C8 C7 -61.9(2) . . . . ?
C19 C14 C9 N17 -178.77(18) . . . . ?
C19 C14 C9 C10 54.8(3) . . . . ?
C19 C18 C6 O3 -174.71(19) . . . . ?
C19 C18 C6 C7 -55.3(2) . . . . ?
C19 C18 C6 C5 57.8(3) . . . . ?
C16 N17 C9 C14 -66.8(2) . . . . ?
C16 N17 C9 C10 57.9(2) . . . . ?
C12 C13 C14 C8 -169.23(16) . . . . ?
C12 C13 C14 C9 66.5(2) . . . . ?
C12 C13 C14 C19 -55.5(2) . . . . ?
C12 C13 C5 O2 -11.9(2) . . . . ?
C12 C13 C5 C6 110.5(2) . . . . ?
C12 C13 C15 C16 -66.4(3) . . . . ?
C12 C11 C1 C2 -2.1(3) . . . . ?
C1 C11 C12 C13 172.2(2) . . . . ?
C1 C11 C12 C4 10.4(3) . . . . ?
C2 C3 C4 O2 -168.2(2) . . . . ?
C2 C3 C4 C12 5.5(4) . . . . ?
C4 O2 C5 C13 11.2(2) . . . . ?
C4 O2 C5 C6 -107.5(2) . . . . ?
C4 C3 C2 C1 2.7(4) . . . . ?
C15 C13 C14 C8 67.2(2) . . . . ?
C15 C13 C14 C9 -57.1(2) . . . . ?
C15 C13 C14 C19 -179.10(17) . . . . ?
C15 C13 C5 O2 110.3(2) . . . . ?
C15 C13 C5 C6 -127.3(2) . . . . ?
C15 C13 C12 C11 83.9(3) . . . . ?
C15 C13 C12 C4 -112.5(2) . . . . ?
C22 C20 C21 F1 -69.1(2) . . . . ?
C22 C20 C21 F2 171.21(17) . . . . ?
C22 C20 C21 F3 50.0(2) . . . . ?
C23 N17 C9 C14 167.41(19) . . . . ?
C23 N17 C9 C10 -68.0(3) . . . . ?
C23 N17 C16 C15 -173.8(2) . . . . ?
C24 O1 C3 C2 -20.4(4) . . . . ?
C24 O1 C3 C4 162.4(2) . . . . ?
C25 O3 C6 C7 176.3(2) . . . . ?
C25 O3 C6 C18 -62.8(3) . . . . ?
C25 O3 C6 C5 63.1(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a needle'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2221027'
loop_
_audit_author_name
_audit_author_address
'Alexander F. Smolyakov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-11-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H32 F3 N O4'
_chemical_formula_sum            'C26 H32 F3 N O4'
_chemical_formula_weight         479.52
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_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                   7.0711(13)
_cell_length_b                   10.670(2)
_cell_length_c                   15.423(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.581(4)
_cell_angle_gamma                90
_cell_volume                     1143.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6748
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1297 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.9047.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             508
_exptl_crystal_recrystallization_method 'crystallized from ???'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13376
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.001
_diffrn_reflns_theta_min         2.334
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.861
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.946
_reflns_number_gt                5535
_reflns_number_total             6467
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2319 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         6467
_refine_ls_number_restraints     119
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.2041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1102
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C7-C20B
 1.5 with sigma of 0.01
 C22B-C20B
 1.5 with sigma of 0.01
2. Rigid body (RIGU) restrains
 C20B, C22B, H22A, O4, C23, H23A, H23B, C24, H24A, H24B, H24C, C21A, F3A, F1A,
 F2A, H22B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(H7B)=Sof(C21B)=Sof(O4')=Sof(H4')=Sof(C23')=
 Sof(H23C)=Sof(H23D)=Sof(C24')=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C22A)=
 Sof(H22C)=Sof(H22D)=Sof(C20A)=1-FVAR(1)
 Sof(H7A)=Sof(C20B)=Sof(C22B)=Sof(H22A)=Sof(H22B)=Sof(O4)=Sof(H4)=Sof(C23)=
 Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C21A)=Sof(F3A)=
 Sof(F1A)=Sof(F2A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7A), C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C22B(H22A,H22B),
 C23(H23A,H23B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C18(H18), C19(H19)
4.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C24(H24A,H24B,
 H24C)
4.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
F1B F 1.104(3) 0.4926(18) 0.5359(12) 0.036(2) Uani 0.392(8) 1 d . U P A 2
F2B F 1.2801(18) 0.4130(14) 0.6459(10) 0.050(2) Uani 0.392(8) 1 d . U P A 2
F3B F 1.0915(11) 0.2944(6) 0.5571(4) 0.0396(13) Uani 0.392(8) 1 d . U P A 2
O1 O 0.8772(3) 0.67295(16) 0.92768(10) 0.0310(4) Uani 1 1 d . . . . .
O2 O 0.6538(3) 0.8310(2) 1.03750(12) 0.0478(5) Uani 1 1 d . . . . .
O3 O 0.8101(3) 0.44028(15) 0.81176(12) 0.0376(4) Uani 1 1 d . . . . .
N17 N 1.2388(3) 0.90405(19) 0.70323(14) 0.0325(4) Uani 1 1 d . . . . .
C1 C 0.7842(4) 1.0483(2) 0.87516(18) 0.0360(5) Uani 1 1 d . . . . .
H1 H 0.7538 1.1324 0.8575 0.043 Uiso 1 1 calc R . . . .
C2 C 0.7182(3) 0.9990(3) 0.94733(17) 0.0366(6) Uani 1 1 d . . . . .
H2 H 0.6511 1.0524 0.9806 0.044 Uiso 1 1 calc R . . . .
C3 C 0.7466(3) 0.8739(3) 0.97284(15) 0.0337(5) Uani 1 1 d . . . . .
C4 C 0.8572(3) 0.8016(2) 0.92549(14) 0.0279(4) Uani 1 1 d . . . . .
C5 C 0.9847(3) 0.6375(2) 0.85865(13) 0.0254(4) Uani 1 1 d . . . . .
H5 H 1.1015 0.5888 0.8858 0.031 Uiso 1 1 calc R . . . .
C6 C 0.8660(3) 0.5596(2) 0.78319(14) 0.0263(4) Uani 1 1 d . . . . .
C7 C 1.0158(3) 0.5362(2) 0.72030(14) 0.0268(4) Uani 1 1 d D . . . .
H7A H 1.1409 0.5247 0.7619 0.032 Uiso 0.608(8) 1 calc R . P A 1
H7B H 1.1417 0.5105 0.7567 0.032 Uiso 0.392(8) 1 calc R . P A 2
C8 C 1.0443(3) 0.65919(19) 0.67108(13) 0.0237(4) Uani 1 1 d . . . . .
H8A H 1.1825 0.6716 0.6699 0.028 Uiso 1 1 calc R . . . .
H8B H 0.9739 0.6544 0.6094 0.028 Uiso 1 1 calc R . . . .
C9 C 1.0268(3) 0.9001(2) 0.69058(15) 0.0277(4) Uani 1 1 d . . . . .
H9 H 0.9760 0.9087 0.6259 0.033 Uiso 1 1 calc R . . . .
C10 C 0.9372(4) 1.0086(2) 0.73844(18) 0.0336(5) Uani 1 1 d . . . . .
H10A H 1.0266 1.0808 0.7450 0.040 Uiso 1 1 calc R . . . .
H10B H 0.8158 1.0357 0.7003 0.040 Uiso 1 1 calc R . . . .
C11 C 0.8952(3) 0.9755(2) 0.82821(17) 0.0300(5) Uani 1 1 d . . . . .
C12 C 0.9416(3) 0.8569(2) 0.86126(15) 0.0262(4) Uani 1 1 d . . . . .
C13 C 1.0480(3) 0.76004(19) 0.81885(13) 0.0227(4) Uani 1 1 d . . . . .
C14 C 0.9679(3) 0.76960(19) 0.71883(13) 0.0221(4) Uani 1 1 d . . . . .
C15 C 1.2673(3) 0.7775(2) 0.83835(15) 0.0292(5) Uani 1 1 d . . . . .
H15A H 1.3125 0.7811 0.9030 0.035 Uiso 1 1 calc R . . . .
H15B H 1.3289 0.7043 0.8155 0.035 Uiso 1 1 calc R . . . .
C16 C 1.3280(3) 0.8965(2) 0.79653(17) 0.0338(5) Uani 1 1 d . . . . .
H16A H 1.2898 0.9704 0.8281 0.041 Uiso 1 1 calc R . . . .
H16B H 1.4697 0.8977 0.8022 0.041 Uiso 1 1 calc R . . . .
C25 C 1.3086(4) 1.0147(3) 0.6623(2) 0.0448(6) Uani 1 1 d . . . . .
H25A H 1.4478 1.0076 0.6651 0.067 Uiso 1 1 calc GR . . . .
H25B H 1.2810 1.0902 0.6940 0.067 Uiso 1 1 calc GR . . . .
H25C H 1.2438 1.0204 0.6006 0.067 Uiso 1 1 calc GR . . . .
C18 C 0.7015(3) 0.6389(2) 0.73677(14) 0.0264(4) Uani 1 1 d . . . . .
H18 H 0.5711 0.6132 0.7304 0.032 Uiso 1 1 calc R . . . .
C19 C 0.7526(3) 0.7475(2) 0.70548(13) 0.0256(4) Uani 1 1 d . . . . .
H19 H 0.6613 0.8065 0.6770 0.031 Uiso 1 1 calc R . . . .
C20B C 0.9936(11) 0.4141(7) 0.6643(6) 0.0267(13) Uani 0.608(8) 1 d D U P A 1
C21B C 1.100(2) 0.406(2) 0.5998(14) 0.039(3) Uani 0.392(8) 1 d . U P A 2
C22B C 0.7984(9) 0.4045(6) 0.6073(4) 0.0306(12) Uani 0.608(8) 1 d D U P A 1
H22A H 0.7756 0.4810 0.5705 0.037 Uiso 0.608(8) 1 calc R U P A 1
H22B H 0.7010 0.4030 0.6459 0.037 Uiso 0.608(8) 1 calc R U P A 1
C26 C 0.7397(5) 0.7276(4) 1.08859(19) 0.0534(8) Uani 1 1 d . . . . .
H26A H 0.6839 0.7198 1.1420 0.080 Uiso 1 1 calc GR . . . .
H26B H 0.8787 0.7413 1.1051 0.080 Uiso 1 1 calc GR . . . .
H26C H 0.7156 0.6505 1.0538 0.080 Uiso 1 1 calc GR . . . .
C27 C 0.6849(5) 0.4375(3) 0.8750(2) 0.0529(8) Uani 1 1 d . . . . .
H27A H 0.6179 0.3568 0.8715 0.079 Uiso 1 1 calc GR . . . .
H27B H 0.5905 0.5054 0.8624 0.079 Uiso 1 1 calc GR . . . .
H27C H 0.7608 0.4485 0.9344 0.079 Uiso 1 1 calc GR . . . .
O4 O 1.0308(8) 0.3083(4) 0.7219(3) 0.0322(9) Uani 0.608(8) 1 d . U P A 1
H4 H 0.9871 0.3222 0.7681 0.048 Uiso 0.608(8) 1 calc GR . P A 1
C23 C 0.7669(7) 0.2895(4) 0.5463(3) 0.0363(12) Uani 0.608(8) 1 d . U P A 1
H23A H 0.8328 0.3032 0.4957 0.044 Uiso 0.608(8) 1 calc R U P A 1
H23B H 0.8253 0.2151 0.5790 0.044 Uiso 0.608(8) 1 calc R U P A 1
C24 C 0.5562(8) 0.2646(6) 0.5122(4) 0.0508(15) Uani 0.608(8) 1 d . U P A 1
H24A H 0.4949 0.2369 0.5609 0.076 Uiso 0.608(8) 1 calc GR U P A 1
H24B H 0.5429 0.1990 0.4669 0.076 Uiso 0.608(8) 1 calc GR U P A 1
H24C H 0.4941 0.3415 0.4865 0.076 Uiso 0.608(8) 1 calc GR U P A 1
O4' O 0.9516(13) 0.3098(6) 0.6987(5) 0.0320(14) Uani 0.392(8) 1 d . U P A 2
H4' H 0.8995 0.3163 0.7432 0.048 Uiso 0.392(8) 1 calc GR . P A 2
C23' C 0.6750(11) 0.3427(7) 0.5174(5) 0.0349(18) Uani 0.392(8) 1 d . U P A 2
H23C H 0.5529 0.3735 0.4818 0.042 Uiso 0.392(8) 1 calc R U P A 2
H23D H 0.7704 0.3372 0.4779 0.042 Uiso 0.392(8) 1 calc R U P A 2
C24' C 0.6418(14) 0.2113(7) 0.5513(6) 0.044(2) Uani 0.392(8) 1 d . U P A 2
H24D H 0.5658 0.2172 0.5983 0.067 Uiso 0.392(8) 1 calc GR U P A 2
H24E H 0.7661 0.1721 0.5746 0.067 Uiso 0.392(8) 1 calc GR U P A 2
H24F H 0.5722 0.1605 0.5028 0.067 Uiso 0.392(8) 1 calc GR U P A 2
C22A C 0.7476(14) 0.4406(9) 0.5917(6) 0.0293(17) Uani 0.392(8) 1 d D U P A 2
H22C H 0.7469 0.5233 0.5625 0.035 Uiso 0.392(8) 1 calc R U P A 2
H22D H 0.6489 0.4445 0.6296 0.035 Uiso 0.392(8) 1 calc R U P A 2
C20A C 0.9411(15) 0.4286(10) 0.6531(8) 0.026(2) Uani 0.392(8) 1 d D U P A 2
C21A C 1.1541(13) 0.4071(11) 0.6091(8) 0.0317(17) Uani 0.608(8) 1 d . U P A 1
F3A F 1.1747(8) 0.2904(4) 0.5799(3) 0.0407(9) Uani 0.608(8) 1 d . U P A 1
F1A F 1.126(2) 0.4817(13) 0.5397(10) 0.049(3) Uani 0.608(8) 1 d . U P A 1
F2A F 1.3276(11) 0.4355(8) 0.6595(6) 0.0447(13) Uani 0.608(8) 1 d . U P A 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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1B C21B 1.36(3) . ?
F2B C21B 1.342(14) . ?
F3B C21B 1.35(2) . ?
O1 C4 1.380(3) . ?
O1 C5 1.467(3) . ?
O2 C3 1.369(3) . ?
O2 C26 1.425(4) . ?
O3 C6 1.427(3) . ?
O3 C27 1.433(3) . ?
N17 C9 1.477(3) . ?
N17 C16 1.463(3) . ?
N17 C25 1.466(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(4) . ?
C1 C11 1.398(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(4) . ?
C3 C4 1.396(3) . ?
C4 C12 1.379(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.546(3) . ?
C5 C13 1.545(3) . ?
C6 C7 1.582(3) . ?
C6 C18 1.508(3) . ?
C7 H7A 1.0000 . ?
C7 H7B 1.0000 . ?
C7 C8 1.547(3) . ?
C7 C20B 1.555(7) . ?
C7 C20A 1.572(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.539(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.568(3) . ?
C9 C14 1.539(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.510(4) . ?
C11 C12 1.381(3) . ?
C12 C13 1.498(3) . ?
C13 C14 1.546(3) . ?
C13 C15 1.536(3) . ?
C14 C19 1.517(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.522(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.330(3) . ?
C19 H19 0.9500 . ?
C20B C22B 1.498(7) . ?
C20B O4 1.431(9) . ?
C20B C21A 1.541(11) . ?
C21B C20A 1.529(19) . ?
C22B H22A 0.9900 . ?
C22B H22B 0.9900 . ?
C22B C23 1.538(7) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
O4 H4 0.8400 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.510(8) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O4' H4' 0.8400 . ?
O4' C20A 1.446(13) . ?
C23' H23C 0.9900 . ?
C23' H23D 0.9900 . ?
C23' C24' 1.530(11) . ?
C23' C22A 1.566(11) . ?
C24' H24D 0.9800 . ?
C24' H24E 0.9800 . ?
C24' H24F 0.9800 . ?
C22A H22C 0.9900 . ?
C22A H22D 0.9900 . ?
C22A C20A 1.519(10) . ?
C21A F3A 1.341(12) . ?
C21A F1A 1.319(18) . ?
C21A F2A 1.361(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C5 107.65(17) . . ?
C3 O2 C26 116.7(2) . . ?
C6 O3 C27 118.01(18) . . ?
C16 N17 C9 111.84(18) . . ?
C16 N17 C25 110.4(2) . . ?
C25 N17 C9 112.3(2) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C11 120.5(2) . . ?
C11 C1 H1 119.7 . . ?
C1 C2 H2 118.8 . . ?
C1 C2 C3 122.5(2) . . ?
C3 C2 H2 118.8 . . ?
O2 C3 C2 117.5(2) . . ?
O2 C3 C4 125.8(2) . . ?
C2 C3 C4 116.5(2) . . ?
O1 C4 C3 127.0(2) . . ?
C12 C4 O1 112.81(19) . . ?
C12 C4 C3 119.8(2) . . ?
O1 C5 H5 109.2 . . ?
O1 C5 C6 113.76(18) . . ?
O1 C5 C13 107.24(16) . . ?
C6 C5 H5 109.2 . . ?
C13 C5 H5 109.2 . . ?
C13 C5 C6 108.21(16) . . ?
O3 C6 C5 112.95(18) . . ?
O3 C6 C7 107.67(16) . . ?
O3 C6 C18 114.44(19) . . ?
C5 C6 C7 102.36(17) . . ?
C18 C6 C5 108.70(17) . . ?
C18 C6 C7 110.01(17) . . ?
C6 C7 H7A 103.9 . . ?
C6 C7 H7B 109.0 . . ?
C8 C7 C6 109.22(17) . . ?
C8 C7 H7A 103.9 . . ?
C8 C7 H7B 109.0 . . ?
C8 C7 C20B 116.6(4) . . ?
C8 C7 C20A 110.7(5) . . ?
C20B C7 C6 117.5(4) . . ?
C20B C7 H7A 103.9 . . ?
C20A C7 C6 109.7(5) . . ?
C20A C7 H7B 109.0 . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C14 C8 C7 109.01(16) . . ?
C14 C8 H8A 109.9 . . ?
C14 C8 H8B 109.9 . . ?
N17 C9 H9 107.4 . . ?
N17 C9 C10 113.90(19) . . ?
N17 C9 C14 108.01(17) . . ?
C10 C9 H9 107.4 . . ?
C14 C9 H9 107.4 . . ?
C14 C9 C10 112.40(18) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 115.05(18) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C1 C11 C10 124.6(2) . . ?
C12 C11 C1 115.9(2) . . ?
C12 C11 C10 118.7(2) . . ?
C4 C12 C11 123.6(2) . . ?
C4 C12 C13 109.65(19) . . ?
C11 C12 C13 125.1(2) . . ?
C5 C13 C14 111.88(16) . . ?
C12 C13 C5 101.85(17) . . ?
C12 C13 C14 105.61(16) . . ?
C12 C13 C15 113.65(17) . . ?
C15 C13 C5 112.35(17) . . ?
C15 C13 C14 111.02(17) . . ?
C8 C14 C9 114.86(17) . . ?
C8 C14 C13 109.32(16) . . ?
C9 C14 C13 105.89(16) . . ?
C19 C14 C8 104.31(17) . . ?
C19 C14 C9 114.79(17) . . ?
C19 C14 C13 107.43(16) . . ?
C13 C15 H15A 109.3 . . ?
C13 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C13 111.81(18) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
N17 C16 C15 111.01(18) . . ?
N17 C16 H16A 109.4 . . ?
N17 C16 H16B 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N17 C25 H25A 109.5 . . ?
N17 C25 H25B 109.5 . . ?
N17 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C6 C18 H18 122.5 . . ?
C19 C18 C6 115.06(19) . . ?
C19 C18 H18 122.5 . . ?
C14 C19 H19 122.6 . . ?
C18 C19 C14 114.77(19) . . ?
C18 C19 H19 122.6 . . ?
C22B C20B C7 111.8(4) . . ?
C22B C20B C21A 111.4(7) . . ?
O4 C20B C7 109.2(5) . . ?
O4 C20B C22B 110.8(6) . . ?
O4 C20B C21A 103.6(6) . . ?
C21A C20B C7 109.8(7) . . ?
F1B C21B C20A 113.2(16) . . ?
F2B C21B F1B 101.7(16) . . ?
F2B C21B F3B 105.2(13) . . ?
F2B C21B C20A 115.2(15) . . ?
F3B C21B F1B 104.6(16) . . ?
F3B C21B C20A 115.5(13) . . ?
C20B C22B H22A 108.4 . . ?
C20B C22B H22B 108.4 . . ?
C20B C22B C23 115.4(5) . . ?
H22A C22B H22B 107.5 . . ?
C23 C22B H22A 108.4 . . ?
C23 C22B H22B 108.4 . . ?
O2 C26 H26A 109.5 . . ?
O2 C26 H26B 109.5 . . ?
O2 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O3 C27 H27A 109.5 . . ?
O3 C27 H27B 109.5 . . ?
O3 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C20B O4 H4 109.5 . . ?
C22B C23 H23A 109.2 . . ?
C22B C23 H23B 109.2 . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 C22B 112.1(4) . . ?
C24 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20A O4' H4' 109.5 . . ?
H23C C23' H23D 107.6 . . ?
C24' C23' H23C 108.7 . . ?
C24' C23' H23D 108.7 . . ?
C24' C23' C22A 114.3(6) . . ?
C22A C23' H23C 108.7 . . ?
C22A C23' H23D 108.7 . . ?
C23' C24' H24D 109.5 . . ?
C23' C24' H24E 109.5 . . ?
C23' C24' H24F 109.5 . . ?
H24D C24' H24E 109.5 . . ?
H24D C24' H24F 109.5 . . ?
H24E C24' H24F 109.5 . . ?
C23' C22A H22C 106.7 . . ?
C23' C22A H22D 106.7 . . ?
H22C C22A H22D 106.6 . . ?
C20A C22A C23' 122.5(8) . . ?
C20A C22A H22C 106.7 . . ?
C20A C22A H22D 106.7 . . ?
C21B C20A C7 106.3(10) . . ?
O4' C20A C7 109.8(8) . . ?
O4' C20A C21B 98.3(10) . . ?
O4' C20A C22A 109.7(8) . . ?
C22A C20A C7 120.3(7) . . ?
C22A C20A C21B 110.2(10) . . ?
F3A C21A C20B 111.5(7) . . ?
F3A C21A F2A 104.8(7) . . ?
F1A C21A C20B 113.7(10) . . ?
F1A C21A F3A 107.3(10) . . ?
F1A C21A F2A 108.5(10) . . ?
F2A C21A C20B 110.6(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1B C21B C20A C7 -78.2(15) . . . . ?
F1B C21B C20A O4' 168.3(13) . . . . ?
F1B C21B C20A C22A 53.7(17) . . . . ?
F2B C21B C20A C7 38.2(18) . . . . ?
F2B C21B C20A O4' -75.3(16) . . . . ?
F2B C21B C20A C22A 170.1(14) . . . . ?
F3B C21B C20A C7 161.3(12) . . . . ?
F3B C21B C20A O4' 47.7(15) . . . . ?
F3B C21B C20A C22A -66.9(17) . . . . ?
O1 C4 C12 C11 160.2(2) . . . . ?
O1 C4 C12 C13 -5.8(3) . . . . ?
O1 C5 C6 O3 -64.6(2) . . . . ?
O1 C5 C6 C7 179.88(16) . . . . ?
O1 C5 C6 C18 63.5(2) . . . . ?
O1 C5 C13 C12 -8.4(2) . . . . ?
O1 C5 C13 C14 -120.76(18) . . . . ?
O1 C5 C13 C15 113.57(19) . . . . ?
O2 C3 C4 O1 7.5(4) . . . . ?
O2 C3 C4 C12 179.4(2) . . . . ?
O3 C6 C7 C8 166.99(19) . . . . ?
O3 C6 C7 C20B 31.3(4) . . . . ?
O3 C6 C7 C20A 45.4(5) . . . . ?
O3 C6 C18 C19 -176.44(18) . . . . ?
N17 C9 C10 C11 -95.5(2) . . . . ?
N17 C9 C14 C8 -56.1(2) . . . . ?
N17 C9 C14 C13 64.7(2) . . . . ?
N17 C9 C14 C19 -177.00(18) . . . . ?
C1 C2 C3 O2 -171.5(2) . . . . ?
C1 C2 C3 C4 4.2(3) . . . . ?
C1 C11 C12 C4 12.2(3) . . . . ?
C1 C11 C12 C13 175.9(2) . . . . ?
C2 C1 C11 C10 165.9(2) . . . . ?
C2 C1 C11 C12 -3.4(3) . . . . ?
C2 C3 C4 O1 -167.8(2) . . . . ?
C2 C3 C4 C12 4.1(3) . . . . ?
C3 C4 C12 C11 -12.8(3) . . . . ?
C3 C4 C12 C13 -178.7(2) . . . . ?
C4 O1 C5 C6 -114.0(2) . . . . ?
C4 O1 C5 C13 5.6(2) . . . . ?
C4 C12 C13 C5 8.5(2) . . . . ?
C4 C12 C13 C14 125.53(19) . . . . ?
C4 C12 C13 C15 -112.5(2) . . . . ?
C5 O1 C4 C3 172.3(2) . . . . ?
C5 O1 C4 C12 -0.1(3) . . . . ?
C5 C6 C7 C8 -73.7(2) . . . . ?
C5 C6 C7 C20B 150.6(4) . . . . ?
C5 C6 C7 C20A 164.7(5) . . . . ?
C5 C6 C18 C19 56.3(2) . . . . ?
C5 C13 C14 C8 -60.7(2) . . . . ?
C5 C13 C14 C9 175.04(17) . . . . ?
C5 C13 C14 C19 51.9(2) . . . . ?
C5 C13 C15 C16 178.33(18) . . . . ?
C6 C5 C13 C12 114.72(18) . . . . ?
C6 C5 C13 C14 2.3(2) . . . . ?
C6 C5 C13 C15 -123.32(19) . . . . ?
C6 C7 C8 C14 16.8(2) . . . . ?
C6 C7 C20B C22B 56.9(7) . . . . ?
C6 C7 C20B O4 -66.0(5) . . . . ?
C6 C7 C20B C21A -178.9(5) . . . . ?
C6 C7 C20A C21B -175.9(9) . . . . ?
C6 C7 C20A O4' -70.6(7) . . . . ?
C6 C7 C20A C22A 58.1(10) . . . . ?
C6 C18 C19 C14 2.4(3) . . . . ?
C7 C6 C18 C19 -55.1(2) . . . . ?
C7 C8 C14 C9 166.86(18) . . . . ?
C7 C8 C14 C13 48.0(2) . . . . ?
C7 C8 C14 C19 -66.6(2) . . . . ?
C7 C20B C22B C23 177.2(5) . . . . ?
C7 C20B C21A F3A 162.3(6) . . . . ?
C7 C20B C21A F1A -76.2(10) . . . . ?
C7 C20B C21A F2A 46.1(9) . . . . ?
C8 C7 C20B C22B -75.5(7) . . . . ?
C8 C7 C20B O4 161.5(4) . . . . ?
C8 C7 C20B C21A 48.6(7) . . . . ?
C8 C7 C20A C21B 63.4(10) . . . . ?
C8 C7 C20A O4' 168.7(6) . . . . ?
C8 C7 C20A C22A -62.5(10) . . . . ?
C8 C14 C19 C18 58.9(2) . . . . ?
C9 N17 C16 C15 57.9(2) . . . . ?
C9 C10 C11 C1 -167.6(2) . . . . ?
C9 C10 C11 C12 1.5(3) . . . . ?
C9 C14 C19 C18 -174.52(18) . . . . ?
C10 C9 C14 C8 177.45(18) . . . . ?
C10 C9 C14 C13 -61.8(2) . . . . ?
C10 C9 C14 C19 56.5(2) . . . . ?
C10 C11 C12 C4 -157.8(2) . . . . ?
C10 C11 C12 C13 5.9(3) . . . . ?
C11 C1 C2 C3 -4.5(4) . . . . ?
C11 C12 C13 C5 -157.1(2) . . . . ?
C11 C12 C13 C14 -40.1(3) . . . . ?
C11 C12 C13 C15 81.8(3) . . . . ?
C12 C13 C14 C8 -170.70(17) . . . . ?
C12 C13 C14 C9 65.0(2) . . . . ?
C12 C13 C14 C19 -58.1(2) . . . . ?
C12 C13 C15 C16 -66.7(2) . . . . ?
C13 C5 C6 O3 176.31(17) . . . . ?
C13 C5 C6 C7 60.8(2) . . . . ?
C13 C5 C6 C18 -55.5(2) . . . . ?
C13 C14 C19 C18 -57.1(2) . . . . ?
C13 C15 C16 N17 -50.1(3) . . . . ?
C14 C9 C10 C11 27.7(3) . . . . ?
C14 C13 C15 C16 52.2(2) . . . . ?
C15 C13 C14 C8 65.7(2) . . . . ?
C15 C13 C14 C9 -58.6(2) . . . . ?
C15 C13 C14 C19 178.31(18) . . . . ?
C16 N17 C9 C10 59.2(2) . . . . ?
C16 N17 C9 C14 -66.4(2) . . . . ?
C25 N17 C9 C10 -65.6(3) . . . . ?
C25 N17 C9 C14 168.8(2) . . . . ?
C25 N17 C16 C15 -176.2(2) . . . . ?
C18 C6 C7 C8 41.7(2) . . . . ?
C18 C6 C7 C20B -94.0(4) . . . . ?
C18 C6 C7 C20A -79.9(5) . . . . ?
C20B C7 C8 C14 153.0(3) . . . . ?
C20B C22B C23 C24 162.7(6) . . . . ?
C22B C20B C21A F3A -73.3(9) . . . . ?
C22B C20B C21A F1A 48.2(11) . . . . ?
C22B C20B C21A F2A 170.4(7) . . . . ?
C26 O2 C3 C2 -154.2(3) . . . . ?
C26 O2 C3 C4 30.5(4) . . . . ?
C27 O3 C6 C5 63.2(3) . . . . ?
C27 O3 C6 C7 175.4(2) . . . . ?
C27 O3 C6 C18 -61.9(3) . . . . ?
O4 C20B C22B C23 -60.8(8) . . . . ?
O4 C20B C21A F3A 45.8(9) . . . . ?
O4 C20B C21A F1A 167.4(9) . . . . ?
O4 C20B C21A F2A -70.4(9) . . . . ?
C23' C22A C20A C7 173.9(8) . . . . ?
C23' C22A C20A C21B 49.8(14) . . . . ?
C23' C22A C20A O4' -57.3(12) . . . . ?
C24' C23' C22A C20A 64.3(11) . . . . ?
C20A C7 C8 C14 137.8(5) . . . . ?
C21A C20B C22B C23 54.0(8) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a needle'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2221036'
loop_
_audit_author_name
_audit_author_address
'Alexander F. Smolyakov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-10-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H34 F3 N O4'
_chemical_formula_sum            'C27 H34 F3 N O4'
_chemical_formula_weight         493.55
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_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'
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                   7.9944(2)
_cell_length_b                   11.8989(3)
_cell_length_c                   25.1140(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2388.96(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6748
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1297 before and 0.0626 after correction.
The Ratio of minimum to maximum transmission is 0.9047.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            25264
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.894
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.748
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4476
_reflns_number_total             4694
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1822 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4694
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²+0.5951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0779
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C22(H22A,H22B),
 C23(H23A,H23B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.67036(16) 0.31045(10) 0.21666(5) 0.0204(3) Uani 1 1 d . . . . .
F2 F 0.73130(18) 0.38759(11) 0.14180(5) 0.0256(3) Uani 1 1 d . . . . .
F3 F 0.86793(16) 0.43336(11) 0.21193(5) 0.0206(3) Uani 1 1 d . . . . .
O1 O 0.75266(19) 0.67584(12) 0.38335(5) 0.0168(3) Uani 1 1 d . . . . .
O2 O 0.9781(2) 0.68908(14) 0.47978(6) 0.0233(4) Uani 1 1 d . . . . .
O3 O 0.80932(19) 0.63923(13) 0.26649(6) 0.0186(3) Uani 1 1 d . . . . .
O4 O 0.6518(2) 0.59926(13) 0.17688(6) 0.0199(3) Uani 1 1 d . . . . .
H4 H 0.716259 0.634557 0.197336 0.030 Uiso 1 1 calc R U . . .
N17 N 0.2355(2) 0.40204(15) 0.38839(7) 0.0173(4) Uani 1 1 d . . . . .
C1 C 0.7152(3) 0.44266(19) 0.50359(8) 0.0179(4) Uani 1 1 d . . . . .
H1 H 0.712772 0.382325 0.528351 0.021 Uiso 1 1 calc R U . . .
C2 C 0.8318(3) 0.52801(19) 0.50965(8) 0.0192(5) Uani 1 1 d . . . . .
H2 H 0.902228 0.527385 0.540112 0.023 Uiso 1 1 calc R U . . .
C3 C 0.8496(3) 0.61487(19) 0.47266(8) 0.0182(4) Uani 1 1 d . . . . .
C4 C 0.7396(3) 0.61344(17) 0.42973(8) 0.0154(4) Uani 1 1 d . . . . .
C5 C 0.6296(3) 0.63099(17) 0.34578(8) 0.0143(4) Uani 1 1 d . . . . .
H5 H 0.560362 0.694279 0.331590 0.017 Uiso 1 1 calc R U . . .
C6 C 0.7092(3) 0.56678(17) 0.29861(8) 0.0146(4) Uani 1 1 d . . . . .
C7 C 0.5540(3) 0.53131(17) 0.26378(8) 0.0137(4) Uani 1 1 d . . . . .
H7 H 0.480202 0.599147 0.263238 0.016 Uiso 1 1 calc R U . . .
C8 C 0.4508(3) 0.44023(17) 0.29362(8) 0.0140(4) Uani 1 1 d . . . . .
H8A H 0.330864 0.460944 0.293566 0.017 Uiso 1 1 calc R U . . .
H8B H 0.462935 0.366884 0.275410 0.017 Uiso 1 1 calc R U . . .
C9 C 0.4077(3) 0.35748(17) 0.38845(8) 0.0147(4) Uani 1 1 d . . . . .
H9 H 0.404108 0.280223 0.372823 0.018 Uiso 1 1 calc R U . . .
C10 C 0.4879(3) 0.34789(18) 0.44558(8) 0.0163(4) Uani 1 1 d . . . . .
H10A H 0.396676 0.342171 0.472085 0.020 Uiso 1 1 calc R U . . .
H10B H 0.553384 0.277356 0.447351 0.020 Uiso 1 1 calc R U . . .
C11 C 0.6009(3) 0.44461(18) 0.46120(8) 0.0155(4) Uani 1 1 d . . . . .
C12 C 0.6114(3) 0.53654(17) 0.42780(8) 0.0140(4) Uani 1 1 d . . . . .
C13 C 0.5161(3) 0.55002(17) 0.37686(8) 0.0134(4) Uani 1 1 d . . . . .
C14 C 0.5148(3) 0.43106(17) 0.35146(8) 0.0135(4) Uani 1 1 d . . . . .
C15 C 0.3382(3) 0.59603(17) 0.38444(8) 0.0163(4) Uani 1 1 d . . . . .
H15A H 0.343478 0.666685 0.405192 0.020 Uiso 1 1 calc R U . . .
H15B H 0.289601 0.613729 0.349166 0.020 Uiso 1 1 calc R U . . .
C16 C 0.2255(3) 0.51312(18) 0.41301(8) 0.0184(4) Uani 1 1 d . . . . .
H16A H 0.259383 0.507795 0.450847 0.022 Uiso 1 1 calc R U . . .
H16B H 0.108552 0.540312 0.411751 0.022 Uiso 1 1 calc R U . . .
C18 C 0.7952(3) 0.46317(17) 0.31998(8) 0.0154(4) Uani 1 1 d . . . . .
H18 H 0.910860 0.448473 0.314802 0.018 Uiso 1 1 calc R U . . .
C19 C 0.6948(3) 0.39452(17) 0.34663(8) 0.0145(4) Uani 1 1 d . . . . .
H19 H 0.733975 0.326275 0.361787 0.017 Uiso 1 1 calc R U . . .
C20 C 0.5867(3) 0.50359(17) 0.20385(8) 0.0161(4) Uani 1 1 d . . . . .
C21 C 0.7137(3) 0.40918(18) 0.19401(8) 0.0173(4) Uani 1 1 d . . . . .
C22 C 0.4234(3) 0.47253(19) 0.17521(8) 0.0174(4) Uani 1 1 d . . . . .
H22A H 0.448369 0.459047 0.137131 0.021 Uiso 1 1 calc R U . . .
H22B H 0.380535 0.401338 0.190368 0.021 Uiso 1 1 calc R U . . .
C23 C 0.2864(3) 0.5616(2) 0.17920(8) 0.0209(5) Uani 1 1 d . . . . .
H23A H 0.336385 0.636778 0.173487 0.025 Uiso 1 1 calc R U . . .
H23B H 0.238071 0.560147 0.215484 0.025 Uiso 1 1 calc R U . . .
C24 C 0.1467(3) 0.5431(2) 0.13847(8) 0.0212(5) Uani 1 1 d . . . . .
H24A H 0.111658 0.463331 0.139781 0.025 Uiso 1 1 calc R U . . .
H24B H 0.049094 0.589564 0.148627 0.025 Uiso 1 1 calc R U . . .
C25 C 0.1968(3) 0.5720(2) 0.08167(9) 0.0256(5) Uani 1 1 d . . . . .
H25A H 0.294657 0.527393 0.071442 0.038 Uiso 1 1 calc R U . . .
H25B H 0.224147 0.652140 0.079409 0.038 Uiso 1 1 calc R U . . .
H25C H 0.103687 0.555118 0.057566 0.038 Uiso 1 1 calc R U . . .
C26 C 0.9651(3) 0.6779(2) 0.28713(10) 0.0280(5) Uani 1 1 d . . . . .
H26A H 1.028468 0.715211 0.258760 0.042 Uiso 1 1 calc R U . . .
H26B H 1.029430 0.613920 0.300680 0.042 Uiso 1 1 calc R U . . .
H26C H 0.944639 0.731313 0.316121 0.042 Uiso 1 1 calc R U . . .
C27 C 0.1160(3) 0.3255(2) 0.41228(9) 0.0229(5) Uani 1 1 d . . . . .
H27A H 0.124236 0.251882 0.394947 0.034 Uiso 1 1 calc R U . . .
H27B H 0.002623 0.355259 0.407711 0.034 Uiso 1 1 calc R U . . .
H27C H 0.140395 0.317487 0.450336 0.034 Uiso 1 1 calc R U . . .
C28 C 0.9490(4) 0.8008(2) 0.46079(10) 0.0302(6) Uani 1 1 d . . . . .
H28A H 0.955956 0.801684 0.421828 0.045 Uiso 1 1 calc R U . . .
H28B H 1.033711 0.851528 0.475589 0.045 Uiso 1 1 calc R U . . .
H28C H 0.837581 0.825735 0.471936 0.045 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 C21 1.351(2) . ?
F2 C21 1.343(2) . ?
F3 C21 1.343(3) . ?
O1 C4 1.385(2) . ?
O1 C5 1.464(2) . ?
O2 C3 1.366(3) . ?
O2 C28 1.432(3) . ?
O3 C6 1.426(2) . ?
O3 C26 1.426(3) . ?
O4 H4 0.8400 . ?
O4 C20 1.423(2) . ?
N17 C9 1.476(3) . ?
N17 C16 1.461(3) . ?
N17 C27 1.450(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(3) . ?
C1 C11 1.403(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(3) . ?
C3 C4 1.391(3) . ?
C4 C12 1.375(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.547(3) . ?
C5 C13 1.536(3) . ?
C6 C7 1.576(3) . ?
C6 C18 1.510(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.555(3) . ?
C7 C20 1.563(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.544(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.575(3) . ?
C9 C14 1.537(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.515(3) . ?
C11 C12 1.381(3) . ?
C12 C13 1.497(3) . ?
C13 C14 1.553(3) . ?
C13 C15 1.536(3) . ?
C14 C19 1.508(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.517(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 H18 0.9500 . ?
C18 C19 1.327(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.534(3) . ?
C20 C22 1.535(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.528(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.530(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.521(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C4 O1 C5 107.22(15) . . ?
C3 O2 C28 115.75(18) . . ?
C26 O3 C6 118.68(16) . . ?
C20 O4 H4 109.5 . . ?
C16 N17 C9 112.03(17) . . ?
C27 N17 C9 112.86(17) . . ?
C27 N17 C16 110.95(17) . . ?
C2 C1 H1 119.7 . . ?
C2 C1 C11 120.6(2) . . ?
C11 C1 H1 119.7 . . ?
C1 C2 H2 118.7 . . ?
C1 C2 C3 122.5(2) . . ?
C3 C2 H2 118.7 . . ?
O2 C3 C2 117.89(19) . . ?
O2 C3 C4 125.8(2) . . ?
C4 C3 C2 116.2(2) . . ?
O1 C4 C3 126.7(2) . . ?
C12 C4 O1 112.52(18) . . ?
C12 C4 C3 120.44(19) . . ?
O1 C5 H5 109.1 . . ?
O1 C5 C6 113.38(17) . . ?
O1 C5 C13 107.33(15) . . ?
C6 C5 H5 109.1 . . ?
C13 C5 H5 109.1 . . ?
C13 C5 C6 108.81(16) . . ?
O3 C6 C5 111.44(16) . . ?
O3 C6 C7 106.84(15) . . ?
O3 C6 C18 116.04(17) . . ?
C5 C6 C7 103.49(16) . . ?
C18 C6 C5 108.57(16) . . ?
C18 C6 C7 109.70(16) . . ?
C6 C7 H7 104.8 . . ?
C8 C7 C6 109.70(16) . . ?
C8 C7 H7 104.8 . . ?
C8 C7 C20 113.94(16) . . ?
C20 C7 C6 117.37(17) . . ?
C20 C7 H7 104.8 . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C14 C8 C7 109.08(16) . . ?
C14 C8 H8A 109.9 . . ?
C14 C8 H8B 109.9 . . ?
N17 C9 H9 107.6 . . ?
N17 C9 C10 114.00(17) . . ?
N17 C9 C14 108.33(16) . . ?
C10 C9 H9 107.6 . . ?
C14 C9 H9 107.6 . . ?
C14 C9 C10 111.41(17) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 115.05(17) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C1 C11 C10 124.91(19) . . ?
C12 C11 C1 115.8(2) . . ?
C12 C11 C10 118.73(18) . . ?
C4 C12 C11 123.42(19) . . ?
C4 C12 C13 109.75(18) . . ?
C11 C12 C13 124.97(19) . . ?
C5 C13 C14 111.53(16) . . ?
C12 C13 C5 101.62(16) . . ?
C12 C13 C14 104.88(16) . . ?
C12 C13 C15 113.78(16) . . ?
C15 C13 C5 112.71(17) . . ?
C15 C13 C14 111.69(17) . . ?
C8 C14 C13 108.93(16) . . ?
C9 C14 C8 115.10(17) . . ?
C9 C14 C13 105.95(16) . . ?
C19 C14 C8 105.12(16) . . ?
C19 C14 C9 114.57(17) . . ?
C19 C14 C13 106.83(17) . . ?
C13 C15 H15A 109.2 . . ?
C13 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C13 112.14(17) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
N17 C16 C15 110.85(17) . . ?
N17 C16 H16A 109.5 . . ?
N17 C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C6 C18 H18 123.0 . . ?
C19 C18 C6 113.99(19) . . ?
C19 C18 H18 123.0 . . ?
C14 C19 H19 121.9 . . ?
C18 C19 C14 116.13(18) . . ?
C18 C19 H19 121.9 . . ?
O4 C20 C7 110.52(16) . . ?
O4 C20 C21 105.48(17) . . ?
O4 C20 C22 106.30(17) . . ?
C21 C20 C7 114.85(16) . . ?
C21 C20 C22 108.12(17) . . ?
C22 C20 C7 111.09(17) . . ?
F1 C21 C20 113.52(17) . . ?
F2 C21 F1 105.76(16) . . ?
F2 C21 F3 105.78(17) . . ?
F2 C21 C20 111.49(17) . . ?
F3 C21 F1 106.30(17) . . ?
F3 C21 C20 113.37(17) . . ?
C20 C22 H22A 108.7 . . ?
C20 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C23 C22 C20 114.32(18) . . ?
C23 C22 H22A 108.7 . . ?
C23 C22 H22B 108.7 . . ?
C22 C23 H23A 109.1 . . ?
C22 C23 H23B 109.1 . . ?
C22 C23 C24 112.30(18) . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C23 C24 H24A 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 C23 113.73(19) . . ?
C25 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
O3 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N17 C27 H27A 109.5 . . ?
N17 C27 H27B 109.5 . . ?
N17 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O2 C28 H28A 109.5 . . ?
O2 C28 H28B 109.5 . . ?
O2 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 C12 C11 160.98(19) . . . . ?
O1 C4 C12 C13 -4.1(2) . . . . ?
O1 C5 C6 O3 -63.7(2) . . . . ?
O1 C5 C6 C7 -178.21(15) . . . . ?
O1 C5 C6 C18 65.3(2) . . . . ?
O1 C5 C13 C12 -12.4(2) . . . . ?
O1 C5 C13 C14 -123.67(17) . . . . ?
O1 C5 C13 C15 109.76(18) . . . . ?
O2 C3 C4 O1 9.3(3) . . . . ?
O2 C3 C4 C12 -177.91(19) . . . . ?
O3 C6 C7 C8 172.85(16) . . . . ?
O3 C6 C7 C20 40.7(2) . . . . ?
O3 C6 C18 C19 -175.75(17) . . . . ?
O4 C20 C21 F1 -179.39(16) . . . . ?
O4 C20 C21 F2 -60.1(2) . . . . ?
O4 C20 C21 F3 59.2(2) . . . . ?
O4 C20 C22 C23 -64.5(2) . . . . ?
N17 C9 C10 C11 -97.7(2) . . . . ?
N17 C9 C14 C8 -56.9(2) . . . . ?
N17 C9 C14 C13 63.5(2) . . . . ?
N17 C9 C14 C19 -178.99(16) . . . . ?
C1 C2 C3 O2 -174.2(2) . . . . ?
C1 C2 C3 C4 2.0(3) . . . . ?
C1 C11 C12 C4 9.8(3) . . . . ?
C1 C11 C12 C13 172.69(19) . . . . ?
C2 C1 C11 C10 169.6(2) . . . . ?
C2 C1 C11 C12 -1.2(3) . . . . ?
C2 C3 C4 O1 -166.48(19) . . . . ?
C2 C3 C4 C12 6.3(3) . . . . ?
C3 C4 C12 C11 -12.8(3) . . . . ?
C3 C4 C12 C13 -177.89(18) . . . . ?
C4 O1 C5 C6 -109.50(18) . . . . ?
C4 O1 C5 C13 10.7(2) . . . . ?
C4 C12 C13 C5 10.1(2) . . . . ?
C4 C12 C13 C14 126.37(18) . . . . ?
C4 C12 C13 C15 -111.29(19) . . . . ?
C5 O1 C4 C3 169.0(2) . . . . ?
C5 O1 C4 C12 -4.3(2) . . . . ?
C5 C6 C7 C8 -69.41(19) . . . . ?
C5 C6 C7 C20 158.48(17) . . . . ?
C5 C6 C18 C19 57.9(2) . . . . ?
C5 C13 C14 C8 -59.6(2) . . . . ?
C5 C13 C14 C9 176.08(16) . . . . ?
C5 C13 C14 C19 53.5(2) . . . . ?
C5 C13 C15 C16 177.45(16) . . . . ?
C6 C5 C13 C12 110.66(17) . . . . ?
C6 C5 C13 C14 -0.6(2) . . . . ?
C6 C5 C13 C15 -127.18(18) . . . . ?
C6 C7 C8 C14 10.6(2) . . . . ?
C6 C7 C20 O4 -61.3(2) . . . . ?
C6 C7 C20 C21 57.9(2) . . . . ?
C6 C7 C20 C22 -179.06(17) . . . . ?
C6 C18 C19 C14 -0.5(3) . . . . ?
C7 C6 C18 C19 -54.6(2) . . . . ?
C7 C8 C14 C9 171.05(17) . . . . ?
C7 C8 C14 C13 52.3(2) . . . . ?
C7 C8 C14 C19 -61.9(2) . . . . ?
C7 C20 C21 F1 58.7(2) . . . . ?
C7 C20 C21 F2 177.99(18) . . . . ?
C7 C20 C21 F3 -62.8(2) . . . . ?
C7 C20 C22 C23 55.8(2) . . . . ?
C8 C7 C20 O4 168.52(17) . . . . ?
C8 C7 C20 C21 -72.3(2) . . . . ?
C8 C7 C20 C22 50.8(2) . . . . ?
C8 C14 C19 C18 60.1(2) . . . . ?
C9 N17 C16 C15 58.4(2) . . . . ?
C9 C10 C11 C1 -164.2(2) . . . . ?
C9 C10 C11 C12 6.5(3) . . . . ?
C9 C14 C19 C18 -172.58(18) . . . . ?
C10 C9 C14 C8 176.91(17) . . . . ?
C10 C9 C14 C13 -62.7(2) . . . . ?
C10 C9 C14 C19 54.8(2) . . . . ?
C10 C11 C12 C4 -161.62(19) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C1 C2 C3 -4.5(3) . . . . ?
C11 C12 C13 C5 -154.7(2) . . . . ?
C11 C12 C13 C14 -38.5(3) . . . . ?
C11 C12 C13 C15 83.9(2) . . . . ?
C12 C13 C14 C8 -168.75(16) . . . . ?
C12 C13 C14 C9 66.9(2) . . . . ?
C12 C13 C14 C19 -55.7(2) . . . . ?
C12 C13 C15 C16 -67.5(2) . . . . ?
C13 C5 C6 O3 176.92(16) . . . . ?
C13 C5 C6 C7 62.4(2) . . . . ?
C13 C5 C6 C18 -54.1(2) . . . . ?
C13 C14 C19 C18 -55.6(2) . . . . ?
C13 C15 C16 N17 -49.8(2) . . . . ?
C14 C9 C10 C11 25.2(2) . . . . ?
C14 C13 C15 C16 51.0(2) . . . . ?
C15 C13 C14 C8 67.6(2) . . . . ?
C15 C13 C14 C9 -56.8(2) . . . . ?
C15 C13 C14 C19 -179.37(16) . . . . ?
C16 N17 C9 C10 57.9(2) . . . . ?
C16 N17 C9 C14 -66.8(2) . . . . ?
C18 C6 C7 C8 46.3(2) . . . . ?
C18 C6 C7 C20 -85.8(2) . . . . ?
C20 C7 C8 C14 144.50(18) . . . . ?
C20 C22 C23 C24 164.35(18) . . . . ?
C21 C20 C22 C23 -177.30(17) . . . . ?
C22 C20 C21 F1 -66.0(2) . . . . ?
C22 C20 C21 F2 53.3(2) . . . . ?
C22 C20 C21 F3 172.56(16) . . . . ?
C22 C23 C24 C25 -73.1(3) . . . . ?
C26 O3 C6 C5 71.9(2) . . . . ?
C26 O3 C6 C7 -175.72(18) . . . . ?
C26 O3 C6 C18 -53.0(2) . . . . ?
C27 N17 C9 C10 -68.2(2) . . . . ?
C27 N17 C9 C14 167.14(17) . . . . ?
C27 N17 C16 C15 -174.45(18) . . . . ?
C28 O2 C3 C2 -149.9(2) . . . . ?
C28 O2 C3 C4 34.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_san436
_database_code_depnum_ccdc_archive 'CCDC 2217268'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;A N Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2022-11-03 deposited with the CCDC.	2023-01-04 downloaded from the CCDC.
;
_audit_creation_date             2022-11-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 F3 N2 O4'
_chemical_formula_sum            'C23 H23 F3 N2 O4'
_chemical_formula_weight         448.43
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_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                   10.0899(7)
_cell_length_b                   7.6365(5)
_cell_length_c                   26.1261(17)
_cell_angle_alpha                90
_cell_angle_beta                 98.814(3)
_cell_angle_gamma                90
_cell_volume                     1989.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9583
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.57
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.5627
_exptl_absorpt_correction_T_min  0.4835
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1152 before and 0.0897 after correction.
The Ratio of minimum to maximum transmission is 0.8593.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0592
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            55164
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_min         2.042
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.865
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                9453
_reflns_number_total             9514
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.143
_refine_ls_abs_structure_details 
;
 Flack x determined using 3749 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.457
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         9514
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0997
_refine_ls_restrained_S_all      1.457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2873
_refine_ls_wR_factor_ref         0.2900
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.775(3)
 0.225(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(O3) \\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
4.a Riding coordinates:
 O4A(H4A), O4(H1B)
4.b Ternary CH refined with riding coordinates:
 C5A(H5A), C7A(H7A), C9A(H9A), C20A(H20A), C5(H5), C7(H7), C9(H9), C20(H20)
4.c Secondary CH2 refined with riding coordinates:
 C8A(H8AA,H8AB), C10A(H10A,H10B), C15A(H15A,H15B), C16A(H16A,H16B), C8(H8A,
 H8B), C10(H3,H4), C15(H6,H8), C16(H10,H11)
4.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C1A(H1A), C2A(H2A), C18A(H18A), C19A(H19A), C2(H2), C18(H18), C19(H19)
4.e Idealised Me refined as rotating group:
 C22A(H22B,H22A,H22C), C23A(H23A,H23B,H23C), C22(H12,H13,H14), C23(H15,H16,H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
C1 C 0.0453(6) 0.0334(8) 0.4829(2) 0.0116(10) Uani 1 1 d . . . . .
H1 H -0.0263 -0.0476 0.4825 0.014 Uiso 1 1 calc R U . . .
C1A C 0.0732(6) 0.9666(10) 0.0367(3) 0.0179(13) Uani 1 1 d . . . . .
H1A H 0.0009 1.0413 0.0416 0.021 Uiso 1 1 calc R U . . .
C2A C 0.0939(7) 0.9231(9) -0.0131(3) 0.0180(13) Uani 1 1 d . . . . .
H2A H 0.0299 0.9596 -0.0416 0.022 Uiso 1 1 calc R U . . .
C3A C 0.2075(7) 0.8259(10) -0.0228(3) 0.0173(13) Uani 1 1 d . . . . .
C4A C 0.2914(7) 0.7631(9) 0.0216(3) 0.0152(12) Uani 1 1 d . . . . .
C5A C 0.4740(6) 0.6630(8) 0.0757(2) 0.0112(10) Uani 1 1 d . U . . .
H5A H 0.5020 0.5381 0.0815 0.013 Uiso 1 1 calc R U . . .
C6A C 0.5965(7) 0.7826(9) 0.0919(2) 0.0117(11) Uani 1 1 d . . . . .
C7A C 0.6468(6) 0.7334(8) 0.1507(2) 0.0095(10) Uani 1 1 d . . . . .
H7A H 0.6567 0.6033 0.1534 0.011 Uiso 1 1 calc R U . . .
C8A C 0.5370(6) 0.7929(9) 0.1843(2) 0.0100(10) Uani 1 1 d . . . . .
H8AA H 0.5135 0.6936 0.2056 0.012 Uiso 1 1 calc R U . . .
H8AB H 0.5728 0.8889 0.2080 0.012 Uiso 1 1 calc R U . . .
C9A C 0.2880(6) 0.9008(10) 0.1742(2) 0.0135(11) Uani 1 1 d . . . . .
H9A H 0.3145 0.9934 0.2009 0.016 Uiso 1 1 calc R U . . .
C10A C 0.1668(6) 0.9695(10) 0.1352(3) 0.0159(12) Uani 1 1 d . . . . .
H10A H 0.0830 0.9374 0.1482 0.019 Uiso 1 1 calc R U . . .
H10B H 0.1713 1.0989 0.1343 0.019 Uiso 1 1 calc R U . . .
C11A C 0.1589(6) 0.9005(9) 0.0799(3) 0.0145(12) Uani 1 1 d . . . . .
C12A C 0.2580(6) 0.7873(9) 0.0693(2) 0.0120(10) Uani 1 1 d . . . . .
C13A C 0.3649(6) 0.7059(8) 0.1091(2) 0.0105(10) Uani 1 1 d . . . . .
C14A C 0.4110(6) 0.8563(8) 0.1481(2) 0.0086(9) Uani 1 1 d . . . . .
C15A C 0.3144(7) 0.5445(9) 0.1350(3) 0.0179(12) Uani 1 1 d . . . . .
H15A H 0.2790 0.4580 0.1081 0.022 Uiso 1 1 calc R U . . .
H15B H 0.3901 0.4896 0.1580 0.022 Uiso 1 1 calc R U . . .
C16A C 0.2043(8) 0.5929(10) 0.1666(3) 0.0210(14) Uani 1 1 d . . . . .
H16A H 0.1209 0.6219 0.1429 0.025 Uiso 1 1 calc R U . . .
H16B H 0.1855 0.4917 0.1880 0.025 Uiso 1 1 calc R U . . .
C17A C 0.2970(8) 0.7170(11) 0.2498(3) 0.0214(14) Uani 1 1 d . . . . .
C18A C 0.5529(6) 0.9720(8) 0.0895(2) 0.0111(10) Uani 1 1 d . . . . .
H18A H 0.5903 1.0575 0.0695 0.013 Uiso 1 1 calc R U . . .
C19A C 0.4568(6) 1.0091(8) 0.1181(2) 0.0099(10) Uani 1 1 d . . . . .
H19A H 0.4200 1.1232 0.1194 0.012 Uiso 1 1 calc R U . . .
C20A C 0.7836(7) 0.8184(9) 0.1717(2) 0.0148(12) Uani 1 1 d . . . . .
H20A H 0.7717 0.9481 0.1736 0.018 Uiso 1 1 calc R U . . .
C21A C 0.8400(7) 0.7499(10) 0.2250(2) 0.0164(13) Uani 1 1 d . . . . .
C22A C 0.1482(9) 0.8196(12) -0.1151(3) 0.0258(16) Uani 1 1 d . . . . .
H22B H 0.1251 0.9442 -0.1180 0.039 Uiso 1 1 calc R U . . .
H22A H 0.0674 0.7509 -0.1128 0.039 Uiso 1 1 calc R U . . .
H22C H 0.1864 0.7831 -0.1457 0.039 Uiso 1 1 calc R U . . .
C23A C 0.6839(7) 0.7773(11) 0.0095(2) 0.0188(13) Uani 1 1 d . . . . .
H23A H 0.6552 0.6696 -0.0094 0.028 Uiso 1 1 calc R U . . .
H23B H 0.7680 0.8184 -0.0007 0.028 Uiso 1 1 calc R U . . .
H23C H 0.6147 0.8674 0.0013 0.028 Uiso 1 1 calc R U . . .
F1A F 0.9618(5) 0.8148(9) 0.2422(2) 0.0311(12) Uani 1 1 d . . . . .
F2A F 0.8524(5) 0.5756(7) 0.22545(18) 0.0258(10) Uani 1 1 d . . . . .
F3A F 0.7654(5) 0.7900(8) 0.26165(16) 0.0261(10) Uani 1 1 d . . . . .
N1A N 0.2458(6) 0.7442(9) 0.2003(2) 0.0189(12) Uani 1 1 d . . . . .
N2A N 0.3387(9) 0.6950(12) 0.2931(3) 0.0312(16) Uani 1 1 d . . . . .
O1A O 0.4141(5) 0.6866(7) 0.02141(17) 0.0141(9) Uani 1 1 d . . . . .
O2A O 0.2445(6) 0.7914(9) -0.0696(2) 0.0258(13) Uani 1 1 d . . . . .
O3A O 0.7038(5) 0.7430(8) 0.06402(17) 0.0172(10) Uani 1 1 d . . . . .
O4A O 0.8840(5) 0.7826(10) 0.14253(19) 0.0236(12) Uani 1 1 d . . . . .
H4A H 0.8533 0.7552 0.1097 0.028 Uiso 1 1 d R U . . .
C2 C 0.1160(7) 0.0905(9) 0.5307(2) 0.0126(11) Uani 1 1 d . . . . .
H2 H 0.0860 0.0558 0.5620 0.015 Uiso 1 1 calc R U . . .
C3 C 0.2290(7) 0.1970(9) 0.5331(2) 0.0126(11) Uani 1 1 d . . . . .
C4 C 0.2607(6) 0.2598(8) 0.4858(2) 0.0108(11) Uani 1 1 d . . . . .
C5 C 0.3774(6) 0.3541(8) 0.4226(2) 0.0095(10) Uani 1 1 d . . . . .
H5 H 0.3921 0.4779 0.4123 0.011 Uiso 1 1 calc R U . . .
C6 C 0.4860(6) 0.2397(8) 0.4058(2) 0.0089(10) Uani 1 1 d . . . . .
C7 C 0.4766(6) 0.2675(8) 0.3456(2) 0.0087(10) Uani 1 1 d . . . . .
H7 H 0.4795 0.3964 0.3392 0.010 Uiso 1 1 calc R U . . .
C8 C 0.3385(6) 0.1991(8) 0.3182(2) 0.0102(10) Uani 1 1 d . . . . .
H8A H 0.2909 0.2936 0.2969 0.012 Uiso 1 1 calc R U . . .
H8B H 0.3522 0.1003 0.2950 0.012 Uiso 1 1 calc R U . . .
C9 C 0.1076(6) 0.0772(9) 0.3393(2) 0.0107(10) Uani 1 1 d . . . . .
H9 H 0.1124 -0.0230 0.3151 0.013 Uiso 1 1 calc R U . . .
C10 C 0.0309(6) 0.0129(9) 0.3838(2) 0.0114(11) Uani 1 1 d . . . . .
H3 H -0.0657 0.0394 0.3739 0.014 Uiso 1 1 calc R U . . .
H4 H 0.0403 -0.1159 0.3869 0.014 Uiso 1 1 calc R U . . .
C11 C 0.0790(6) 0.0942(9) 0.4362(2) 0.0115(10) Uani 1 1 d . . . . .
C12 C 0.1788(6) 0.2176(9) 0.4401(2) 0.0115(10) Uani 1 1 d . . . . .
C13 C 0.2375(6) 0.2936(9) 0.3959(2) 0.0107(10) Uani 1 1 d . . . . .
C14 C 0.2529(6) 0.1375(8) 0.3594(2) 0.0078(10) Uani 1 1 d . . . . .
C15 C 0.1537(7) 0.4439(9) 0.3676(2) 0.0125(11) Uani 1 1 d . . . . .
H6 H 0.1399 0.5364 0.3928 0.015 Uiso 1 1 calc R U . . .
H8 H 0.2029 0.4960 0.3413 0.015 Uiso 1 1 calc R U . . .
C16 C 0.0171(7) 0.3759(9) 0.3411(2) 0.0153(12) Uani 1 1 d . . . . .
H10 H -0.0399 0.3488 0.3677 0.018 Uiso 1 1 calc R U . . .
H11 H -0.0283 0.4683 0.3182 0.018 Uiso 1 1 calc R U . . .
C17 C 0.0424(6) 0.2355(10) 0.2604(3) 0.0150(12) Uani 1 1 d . . . . .
C18 C 0.4569(5) 0.0473(8) 0.4136(2) 0.0079(10) Uani 1 1 d . . . . .
H18 H 0.5185 -0.0299 0.4334 0.010 Uiso 1 1 calc R U . . .
C19 C 0.3348(6) -0.0033(8) 0.3896(2) 0.0079(10) Uani 1 1 d . U . . .
H19 H 0.3028 -0.1197 0.3917 0.009 Uiso 1 1 calc R U . . .
C20 C 0.5875(6) 0.1850(9) 0.3217(2) 0.0106(10) Uani 1 1 d . . . . .
H20 H 0.5674 0.0573 0.3170 0.013 Uiso 1 1 calc R U . . .
C21 C 0.5995(7) 0.2618(10) 0.2689(3) 0.0158(12) Uani 1 1 d . . . . .
C22 C 0.2863(7) 0.1889(11) 0.6253(2) 0.0193(13) Uani 1 1 d . . . . .
H12 H 0.2737 0.0617 0.6243 0.029 Uiso 1 1 calc R U . . .
H13 H 0.2044 0.2457 0.6329 0.029 Uiso 1 1 calc R U . . .
H14 H 0.3614 0.2190 0.6522 0.029 Uiso 1 1 calc R U . . .
C23 C 0.6574(7) 0.2553(10) 0.4830(3) 0.0193(13) Uani 1 1 d . . . . .
H15 H 0.7507 0.2151 0.4884 0.029 Uiso 1 1 calc R U . . .
H16 H 0.5997 0.1628 0.4934 0.029 Uiso 1 1 calc R U . . .
H17 H 0.6497 0.3602 0.5040 0.029 Uiso 1 1 calc R U . . .
F1 F 0.6988(5) 0.1905(8) 0.24727(18) 0.0253(10) Uani 1 1 d . . . . .
F2 F 0.6228(6) 0.4333(7) 0.27135(19) 0.0267(10) Uani 1 1 d . . . . .
F3 F 0.4867(5) 0.2341(8) 0.23508(16) 0.0262(11) Uani 1 1 d . . . . .
N1 N 0.0318(6) 0.2181(8) 0.3103(2) 0.0159(11) Uani 1 1 d . . . . .
N2 N 0.0493(7) 0.2445(10) 0.2167(2) 0.0239(13) Uani 1 1 d . . . . .
O1 O 0.3744(5) 0.3478(7) 0.47842(16) 0.0115(8) Uani 1 1 d . . . . .
O2 O 0.3142(6) 0.2473(8) 0.57662(17) 0.0195(10) Uani 1 1 d . . . . .
O3 O 0.6163(5) 0.2964(7) 0.42882(17) 0.0154(9) Uani 1 1 d . U . . .
O4 O 0.7187(5) 0.2023(11) 0.3500(2) 0.0265(13) Uani 1 1 d . . . . .
H1B H 0.7179 0.2576 0.3822 0.032 Uiso 1 1 d 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
C1 H1 0.9500 . ?
C1 C2 1.409(8) . ?
C1 C11 1.396(8) . ?
C1A H1A 0.9500 . ?
C1A C2A 1.389(10) . ?
C1A C11A 1.407(9) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.422(9) . ?
C3A C4A 1.411(8) . ?
C3A O2A 1.357(9) . ?
C4A C12A 1.354(9) . ?
C4A O1A 1.370(8) . ?
C5A H5A 1.0000 . ?
C5A C6A 1.543(9) . ?
C5A C13A 1.540(9) . ?
C5A O1A 1.466(6) . ?
C6A C7A 1.588(8) . ?
C6A C18A 1.510(9) . ?
C6A O3A 1.426(8) . ?
C7A H7A 1.0000 . ?
C7A C8A 1.583(8) . ?
C7A C20A 1.548(8) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C8A C14A 1.542(8) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.558(9) . ?
C9A C14A 1.544(8) . ?
C9A N1A 1.472(9) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A C11A 1.527(9) . ?
C11A C12A 1.381(9) . ?
C12A C13A 1.512(7) . ?
C13A C14A 1.558(8) . ?
C13A C15A 1.530(9) . ?
C14A C19A 1.517(8) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C15A C16A 1.527(10) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C16A N1A 1.474(10) . ?
C17A N1A 1.334(9) . ?
C17A N2A 1.156(11) . ?
C18A H18A 0.9500 . ?
C18A C19A 1.341(9) . ?
C19A H19A 0.9500 . ?
C20A H20A 1.0000 . ?
C20A C21A 1.515(8) . ?
C20A O4A 1.386(9) . ?
C21A F1A 1.337(8) . ?
C21A F2A 1.337(9) . ?
C21A F3A 1.341(8) . ?
C22A H22B 0.9800 . ?
C22A H22A 0.9800 . ?
C22A H22C 0.9800 . ?
C22A O2A 1.431(8) . ?
C23A H23A 0.9800 . ?
C23A H23B 0.9800 . ?
C23A H23C 0.9800 . ?
C23A O3A 1.432(7) . ?
O4A H4A 0.8911 . ?
C2 H2 0.9500 . ?
C2 C3 1.395(9) . ?
C3 C4 1.407(8) . ?
C3 O2 1.371(7) . ?
C4 C12 1.382(8) . ?
C4 O1 1.368(7) . ?
C5 H5 1.0000 . ?
C5 C6 1.517(9) . ?
C5 C13 1.546(8) . ?
C5 O1 1.465(6) . ?
C6 C7 1.575(7) . ?
C6 C18 1.518(9) . ?
C6 O3 1.426(7) . ?
C7 H7 1.0000 . ?
C7 C8 1.556(8) . ?
C7 C20 1.502(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.553(8) . ?
C9 H9 1.0000 . ?
C9 C10 1.571(8) . ?
C9 C14 1.549(8) . ?
C9 N1 1.463(8) . ?
C10 H3 0.9900 . ?
C10 H4 0.9900 . ?
C10 C11 1.513(8) . ?
C11 C12 1.372(9) . ?
C12 C13 1.493(8) . ?
C13 C14 1.549(8) . ?
C13 C15 1.545(8) . ?
C14 C19 1.504(8) . ?
C15 H6 0.9900 . ?
C15 H8 0.9900 . ?
C15 C16 1.535(9) . ?
C16 H10 0.9900 . ?
C16 H11 0.9900 . ?
C16 N1 1.468(9) . ?
C17 N1 1.333(8) . ?
C17 N2 1.157(10) . ?
C18 H18 0.9500 . ?
C18 C19 1.350(7) . ?
C19 H19 0.9500 . ?
C20 H20 1.0000 . ?
C20 C21 1.520(8) . ?
C20 O4 1.421(7) . ?
C21 F1 1.339(8) . ?
C21 F2 1.331(9) . ?
C21 F3 1.346(8) . ?
C22 H12 0.9800 . ?
C22 H13 0.9800 . ?
C22 H14 0.9800 . ?
C22 O2 1.415(7) . ?
C23 H15 0.9800 . ?
C23 H16 0.9800 . ?
C23 H17 0.9800 . ?
C23 O3 1.448(7) . ?
O4 H1B 0.9429 . ?

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 C1 H1 119.5 . . ?
C11 C1 H1 119.5 . . ?
C11 C1 C2 121.0(6) . . ?
C2A C1A H1A 119.8 . . ?
C2A C1A C11A 120.3(6) . . ?
C11A C1A H1A 119.8 . . ?
C1A C2A H2A 118.9 . . ?
C1A C2A C3A 122.2(6) . . ?
C3A C2A H2A 118.9 . . ?
C4A C3A C2A 115.4(6) . . ?
O2A C3A C2A 127.1(6) . . ?
O2A C3A C4A 117.5(6) . . ?
C12A C4A C3A 120.6(6) . . ?
C12A C4A O1A 114.5(6) . . ?
O1A C4A C3A 124.8(6) . . ?
C6A C5A H5A 109.1 . . ?
C13A C5A H5A 109.1 . . ?
C13A C5A C6A 109.4(5) . . ?
O1A C5A H5A 109.1 . . ?
O1A C5A C6A 112.7(5) . . ?
O1A C5A C13A 107.3(4) . . ?
C5A C6A C7A 104.4(5) . . ?
C18A C6A C5A 109.8(5) . . ?
C18A C6A C7A 108.3(5) . . ?
O3A C6A C5A 111.9(5) . . ?
O3A C6A C7A 106.8(5) . . ?
O3A C6A C18A 114.9(5) . . ?
C6A C7A H7A 108.5 . . ?
C8A C7A C6A 108.8(5) . . ?
C8A C7A H7A 108.5 . . ?
C20A C7A C6A 112.3(5) . . ?
C20A C7A H7A 108.5 . . ?
C20A C7A C8A 110.1(5) . . ?
C7A C8A H8AA 109.8 . . ?
C7A C8A H8AB 109.8 . . ?
H8AA C8A H8AB 108.3 . . ?
C14A C8A C7A 109.2(4) . . ?
C14A C8A H8AA 109.8 . . ?
C14A C8A H8AB 109.8 . . ?
C10A C9A H9A 108.5 . . ?
C14A C9A H9A 108.5 . . ?
C14A C9A C10A 112.9(5) . . ?
N1A C9A H9A 108.5 . . ?
N1A C9A C10A 108.9(5) . . ?
N1A C9A C14A 109.6(6) . . ?
C9A C10A H10A 108.5 . . ?
C9A C10A H10B 108.5 . . ?
H10A C10A H10B 107.5 . . ?
C11A C10A C9A 115.1(5) . . ?
C11A C10A H10A 108.5 . . ?
C11A C10A H10B 108.5 . . ?
C1A C11A C10A 124.9(6) . . ?
C12A C11A C1A 116.0(6) . . ?
C12A C11A C10A 118.1(5) . . ?
C4A C12A C11A 124.1(6) . . ?
C4A C12A C13A 108.9(6) . . ?
C11A C12A C13A 125.6(6) . . ?
C5A C13A C14A 111.0(5) . . ?
C12A C13A C5A 101.3(5) . . ?
C12A C13A C14A 104.8(5) . . ?
C12A C13A C15A 112.6(5) . . ?
C15A C13A C5A 113.2(5) . . ?
C15A C13A C14A 113.0(5) . . ?
C8A C14A C9A 116.1(5) . . ?
C8A C14A C13A 107.8(5) . . ?
C9A C14A C13A 105.8(5) . . ?
C19A C14A C8A 105.7(5) . . ?
C19A C14A C9A 112.8(5) . . ?
C19A C14A C13A 108.3(5) . . ?
C13A C15A H15A 109.4 . . ?
C13A C15A H15B 109.4 . . ?
H15A C15A H15B 108.0 . . ?
C16A C15A C13A 111.3(6) . . ?
C16A C15A H15A 109.4 . . ?
C16A C15A H15B 109.4 . . ?
C15A C16A H16A 109.6 . . ?
C15A C16A H16B 109.6 . . ?
H16A C16A H16B 108.1 . . ?
N1A C16A C15A 110.4(6) . . ?
N1A C16A H16A 109.6 . . ?
N1A C16A H16B 109.6 . . ?
N2A C17A N1A 178.4(10) . . ?
C6A C18A H18A 122.9 . . ?
C19A C18A C6A 114.2(6) . . ?
C19A C18A H18A 122.9 . . ?
C14A C19A H19A 122.3 . . ?
C18A C19A C14A 115.4(5) . . ?
C18A C19A H19A 122.3 . . ?
C7A C20A H20A 109.1 . . ?
C21A C20A C7A 111.8(5) . . ?
C21A C20A H20A 109.1 . . ?
O4A C20A C7A 114.2(5) . . ?
O4A C20A H20A 109.1 . . ?
O4A C20A C21A 103.5(5) . . ?
F1A C21A C20A 112.2(6) . . ?
F1A C21A F3A 105.3(6) . . ?
F2A C21A C20A 111.9(6) . . ?
F2A C21A F1A 106.6(6) . . ?
F2A C21A F3A 106.4(6) . . ?
F3A C21A C20A 113.8(6) . . ?
H22B C22A H22A 109.5 . . ?
H22B C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
O2A C22A H22B 109.5 . . ?
O2A C22A H22A 109.5 . . ?
O2A C22A H22C 109.5 . . ?
H23A C23A H23B 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
O3A C23A H23A 109.5 . . ?
O3A C23A H23B 109.5 . . ?
O3A C23A H23C 109.5 . . ?
C9A N1A C16A 115.8(5) . . ?
C17A N1A C9A 118.6(6) . . ?
C17A N1A C16A 119.4(7) . . ?
C4A O1A C5A 106.7(5) . . ?
C3A O2A C22A 118.3(6) . . ?
C6A O3A C23A 117.8(5) . . ?
C20A O4A H4A 113.5 . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.2(5) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 117.0(5) . . ?
O2 C3 C2 127.2(5) . . ?
O2 C3 C4 115.8(6) . . ?
C12 C4 C3 119.6(6) . . ?
O1 C4 C3 126.8(5) . . ?
O1 C4 C12 113.3(5) . . ?
C6 C5 H5 108.9 . . ?
C6 C5 C13 110.4(5) . . ?
C13 C5 H5 108.9 . . ?
O1 C5 H5 108.9 . . ?
O1 C5 C6 113.2(5) . . ?
O1 C5 C13 106.4(5) . . ?
C5 C6 C7 105.9(5) . . ?
C5 C6 C18 110.8(5) . . ?
C18 C6 C7 106.3(5) . . ?
O3 C6 C5 111.3(5) . . ?
O3 C6 C7 106.9(4) . . ?
O3 C6 C18 115.0(5) . . ?
C6 C7 H7 107.5 . . ?
C8 C7 C6 109.1(4) . . ?
C8 C7 H7 107.5 . . ?
C20 C7 C6 115.1(5) . . ?
C20 C7 H7 107.5 . . ?
C20 C7 C8 109.8(5) . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C14 C8 C7 109.7(4) . . ?
C14 C8 H8A 109.7 . . ?
C14 C8 H8B 109.7 . . ?
C10 C9 H9 107.9 . . ?
C14 C9 H9 107.9 . . ?
C14 C9 C10 113.0(4) . . ?
N1 C9 H9 107.9 . . ?
N1 C9 C10 109.6(5) . . ?
N1 C9 C14 110.5(5) . . ?
C9 C10 H3 108.6 . . ?
C9 C10 H4 108.6 . . ?
H3 C10 H4 107.6 . . ?
C11 C10 C9 114.5(5) . . ?
C11 C10 H3 108.6 . . ?
C11 C10 H4 108.6 . . ?
C1 C11 C10 124.5(6) . . ?
C12 C11 C1 116.0(5) . . ?
C12 C11 C10 118.6(5) . . ?
C4 C12 C13 108.8(5) . . ?
C11 C12 C4 124.0(6) . . ?
C11 C12 C13 125.7(5) . . ?
C5 C13 C14 109.7(5) . . ?
C12 C13 C5 102.1(4) . . ?
C12 C13 C14 105.4(5) . . ?
C12 C13 C15 114.0(5) . . ?
C15 C13 C5 112.9(5) . . ?
C15 C13 C14 112.1(5) . . ?
C9 C14 C8 117.0(4) . . ?
C9 C14 C13 104.9(5) . . ?
C13 C14 C8 108.2(5) . . ?
C19 C14 C8 105.2(5) . . ?
C19 C14 C9 112.4(5) . . ?
C19 C14 C13 109.0(4) . . ?
C13 C15 H6 109.5 . . ?
C13 C15 H8 109.5 . . ?
H6 C15 H8 108.1 . . ?
C16 C15 C13 110.6(5) . . ?
C16 C15 H6 109.5 . . ?
C16 C15 H8 109.5 . . ?
C15 C16 H10 109.3 . . ?
C15 C16 H11 109.3 . . ?
H10 C16 H11 108.0 . . ?
N1 C16 C15 111.4(5) . . ?
N1 C16 H10 109.3 . . ?
N1 C16 H11 109.3 . . ?
N2 C17 N1 177.4(8) . . ?
C6 C18 H18 123.3 . . ?
C19 C18 C6 113.4(5) . . ?
C19 C18 H18 123.3 . . ?
C14 C19 H19 122.3 . . ?
C18 C19 C14 115.3(5) . . ?
C18 C19 H19 122.3 . . ?
C7 C20 H20 108.0 . . ?
C7 C20 C21 112.6(5) . . ?
C21 C20 H20 108.0 . . ?
O4 C20 C7 116.0(5) . . ?
O4 C20 H20 108.0 . . ?
O4 C20 C21 103.9(5) . . ?
F1 C21 C20 113.2(6) . . ?
F1 C21 F3 105.7(5) . . ?
F2 C21 C20 112.0(5) . . ?
F2 C21 F1 106.4(6) . . ?
F2 C21 F3 108.2(6) . . ?
F3 C21 C20 111.0(5) . . ?
H12 C22 H13 109.5 . . ?
H12 C22 H14 109.5 . . ?
H13 C22 H14 109.5 . . ?
O2 C22 H12 109.5 . . ?
O2 C22 H13 109.5 . . ?
O2 C22 H14 109.5 . . ?
H15 C23 H16 109.5 . . ?
H15 C23 H17 109.5 . . ?
H16 C23 H17 109.5 . . ?
O3 C23 H15 109.5 . . ?
O3 C23 H16 109.5 . . ?
O3 C23 H17 109.5 . . ?
C9 N1 C16 114.2(5) . . ?
C17 N1 C9 117.8(6) . . ?
C17 N1 C16 118.9(6) . . ?
C4 O1 C5 107.6(4) . . ?
C3 O2 C22 118.1(6) . . ?
C6 O3 C23 117.0(5) . . ?
C20 O4 H1B 111.8 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 6.6(10) . . . . ?
C1 C2 C3 O2 -173.0(6) . . . . ?
C1 C11 C12 C4 11.7(10) . . . . ?
C1 C11 C12 C13 176.0(6) . . . . ?
C1A C2A C3A C4A 5.5(10) . . . . ?
C1A C2A C3A O2A -172.9(7) . . . . ?
C1A C11A C12A C4A 12.4(10) . . . . ?
C1A C11A C12A C13A 177.4(6) . . . . ?
C2A C1A C11A C10A 165.5(7) . . . . ?
C2A C1A C11A C12A -2.6(10) . . . . ?
C2A C3A C4A C12A 3.8(10) . . . . ?
C2A C3A C4A O1A -171.2(6) . . . . ?
C2A C3A O2A C22A -14.9(12) . . . . ?
C3A C4A C12A C11A -13.3(10) . . . . ?
C3A C4A C12A C13A 179.6(6) . . . . ?
C3A C4A O1A C5A 172.5(6) . . . . ?
C4A C3A O2A C22A 166.7(7) . . . . ?
C4A C12A C13A C5A 9.8(7) . . . . ?
C4A C12A C13A C14A 125.3(6) . . . . ?
C4A C12A C13A C15A -111.5(7) . . . . ?
C5A C6A C7A C8A -67.0(6) . . . . ?
C5A C6A C7A C20A 170.8(5) . . . . ?
C5A C6A C18A C19A 56.0(7) . . . . ?
C5A C6A O3A C23A 66.8(8) . . . . ?
C5A C13A C14A C8A -61.7(6) . . . . ?
C5A C13A C14A C9A 173.5(5) . . . . ?
C5A C13A C14A C19A 52.3(6) . . . . ?
C5A C13A C15A C16A -178.7(5) . . . . ?
C6A C5A C13A C12A 111.4(5) . . . . ?
C6A C5A C13A C14A 0.5(6) . . . . ?
C6A C5A C13A C15A -127.8(5) . . . . ?
C6A C5A O1A C4A -111.4(6) . . . . ?
C6A C7A C8A C14A 7.3(6) . . . . ?
C6A C7A C20A C21A -171.7(5) . . . . ?
C6A C7A C20A O4A -54.6(7) . . . . ?
C6A C18A C19A C14A 0.9(7) . . . . ?
C7A C6A C18A C19A -57.4(7) . . . . ?
C7A C6A O3A C23A -179.5(6) . . . . ?
C7A C8A C14A C9A 173.7(5) . . . . ?
C7A C8A C14A C13A 55.3(6) . . . . ?
C7A C8A C14A C19A -60.3(6) . . . . ?
C7A C20A C21A F1A 176.3(6) . . . . ?
C7A C20A C21A F2A 56.5(8) . . . . ?
C7A C20A C21A F3A -64.3(8) . . . . ?
C8A C7A C20A C21A 66.9(7) . . . . ?
C8A C7A C20A O4A -176.1(6) . . . . ?
C8A C14A C19A C18A 59.8(6) . . . . ?
C9A C10A C11A C1A -168.4(6) . . . . ?
C9A C10A C11A C12A -0.6(9) . . . . ?
C9A C14A C19A C18A -172.3(5) . . . . ?
C10A C9A C14A C8A 178.1(5) . . . . ?
C10A C9A C14A C13A -62.4(6) . . . . ?
C10A C9A C14A C19A 55.8(7) . . . . ?
C10A C9A N1A C16A 62.7(8) . . . . ?
C10A C9A N1A C17A -145.1(7) . . . . ?
C10A C11A C12A C4A -156.5(7) . . . . ?
C10A C11A C12A C13A 8.4(10) . . . . ?
C11A C1A C2A C3A -6.1(11) . . . . ?
C11A C12A C13A C5A -157.1(7) . . . . ?
C11A C12A C13A C14A -41.5(8) . . . . ?
C11A C12A C13A C15A 81.7(8) . . . . ?
C12A C4A O1A C5A -2.8(8) . . . . ?
C12A C13A C14A C8A -170.2(5) . . . . ?
C12A C13A C14A C9A 65.0(6) . . . . ?
C12A C13A C14A C19A -56.2(6) . . . . ?
C12A C13A C15A C16A -64.6(7) . . . . ?
C13A C5A C6A C7A 62.0(6) . . . . ?
C13A C5A C6A C18A -54.0(6) . . . . ?
C13A C5A C6A O3A 177.1(5) . . . . ?
C13A C5A O1A C4A 9.1(7) . . . . ?
C13A C14A C19A C18A -55.6(7) . . . . ?
C13A C15A C16A N1A -48.7(8) . . . . ?
C14A C9A C10A C11A 29.0(8) . . . . ?
C14A C9A N1A C16A -61.2(7) . . . . ?
C14A C9A N1A C17A 91.1(8) . . . . ?
C14A C13A C15A C16A 54.0(7) . . . . ?
C15A C13A C14A C8A 66.8(6) . . . . ?
C15A C13A C14A C9A -58.0(6) . . . . ?
C15A C13A C14A C19A -179.2(5) . . . . ?
C15A C16A N1A C9A 54.3(8) . . . . ?
C15A C16A N1A C17A -97.7(8) . . . . ?
C18A C6A C7A C8A 50.0(6) . . . . ?
C18A C6A C7A C20A -72.2(6) . . . . ?
C18A C6A O3A C23A -59.4(8) . . . . ?
C20A C7A C8A C14A 130.8(5) . . . . ?
N1A C9A C10A C11A -93.0(7) . . . . ?
N1A C9A C14A C8A -60.4(7) . . . . ?
N1A C9A C14A C13A 59.1(6) . . . . ?
N1A C9A C14A C19A 177.3(5) . . . . ?
O1A C4A C12A C11A 162.2(6) . . . . ?
O1A C4A C12A C13A -4.9(8) . . . . ?
O1A C5A C6A C7A -178.8(5) . . . . ?
O1A C5A C6A C18A 65.3(6) . . . . ?
O1A C5A C6A O3A -63.6(7) . . . . ?
O1A C5A C13A C12A -11.2(6) . . . . ?
O1A C5A C13A C14A -122.1(5) . . . . ?
O1A C5A C13A C15A 109.6(6) . . . . ?
O2A C3A C4A C12A -177.6(7) . . . . ?
O2A C3A C4A O1A 7.4(10) . . . . ?
O3A C6A C7A C8A 174.3(5) . . . . ?
O3A C6A C7A C20A 52.1(6) . . . . ?
O3A C6A C18A C19A -176.7(5) . . . . ?
O4A C20A C21A F1A 53.0(8) . . . . ?
O4A C20A C21A F2A -66.9(7) . . . . ?
O4A C20A C21A F3A 172.4(6) . . . . ?
C2 C1 C11 C10 166.0(6) . . . . ?
C2 C1 C11 C12 -3.2(9) . . . . ?
C2 C3 C4 C12 1.4(9) . . . . ?
C2 C3 C4 O1 -171.7(6) . . . . ?
C2 C3 O2 C22 -0.9(10) . . . . ?
C3 C4 C12 C11 -11.1(10) . . . . ?
C3 C4 C12 C13 -177.7(6) . . . . ?
C3 C4 O1 C5 168.2(6) . . . . ?
C4 C3 O2 C22 179.5(6) . . . . ?
C4 C12 C13 C5 10.3(7) . . . . ?
C4 C12 C13 C14 124.9(5) . . . . ?
C4 C12 C13 C15 -111.7(6) . . . . ?
C5 C6 C7 C8 -63.9(6) . . . . ?
C5 C6 C7 C20 172.1(5) . . . . ?
C5 C6 C18 C19 55.1(6) . . . . ?
C5 C6 O3 C23 75.3(7) . . . . ?
C5 C13 C14 C8 -59.8(6) . . . . ?
C5 C13 C14 C9 174.6(5) . . . . ?
C5 C13 C14 C19 54.0(6) . . . . ?
C5 C13 C15 C16 179.0(5) . . . . ?
C6 C5 C13 C12 110.1(6) . . . . ?
C6 C5 C13 C14 -1.3(6) . . . . ?
C6 C5 C13 C15 -127.1(5) . . . . ?
C6 C5 O1 C4 -109.8(6) . . . . ?
C6 C7 C8 C14 3.6(6) . . . . ?
C6 C7 C20 C21 -161.7(5) . . . . ?
C6 C7 C20 O4 -42.2(8) . . . . ?
C6 C18 C19 C14 1.1(7) . . . . ?
C7 C6 C18 C19 -59.5(6) . . . . ?
C7 C6 O3 C23 -169.5(6) . . . . ?
C7 C8 C14 C9 175.7(5) . . . . ?
C7 C8 C14 C13 57.6(6) . . . . ?
C7 C8 C14 C19 -58.8(6) . . . . ?
C7 C20 C21 F1 179.5(5) . . . . ?
C7 C20 C21 F2 59.2(8) . . . . ?
C7 C20 C21 F3 -61.8(7) . . . . ?
C8 C7 C20 C21 74.7(6) . . . . ?
C8 C7 C20 O4 -165.8(6) . . . . ?
C8 C14 C19 C18 59.5(6) . . . . ?
C9 C10 C11 C1 -166.8(6) . . . . ?
C9 C10 C11 C12 2.2(8) . . . . ?
C9 C14 C19 C18 -172.2(5) . . . . ?
C10 C9 C14 C8 178.5(5) . . . . ?
C10 C9 C14 C13 -61.6(6) . . . . ?
C10 C9 C14 C19 56.7(6) . . . . ?
C10 C9 N1 C16 63.2(7) . . . . ?
C10 C9 N1 C17 -150.1(6) . . . . ?
C10 C11 C12 C4 -158.2(6) . . . . ?
C10 C11 C12 C13 6.1(10) . . . . ?
C11 C1 C2 C3 -5.8(10) . . . . ?
C11 C12 C13 C5 -156.0(6) . . . . ?
C11 C12 C13 C14 -41.4(8) . . . . ?
C11 C12 C13 C15 82.0(8) . . . . ?
C12 C4 O1 C5 -5.2(7) . . . . ?
C12 C13 C14 C8 -169.1(5) . . . . ?
C12 C13 C14 C9 65.3(5) . . . . ?
C12 C13 C14 C19 -55.2(6) . . . . ?
C12 C13 C15 C16 -65.1(7) . . . . ?
C13 C5 C6 C7 62.5(6) . . . . ?
C13 C5 C6 C18 -52.4(6) . . . . ?
C13 C5 C6 O3 178.3(4) . . . . ?
C13 C5 O1 C4 11.6(6) . . . . ?
C13 C14 C19 C18 -56.3(7) . . . . ?
C13 C15 C16 N1 -49.1(7) . . . . ?
C14 C9 C10 C11 27.1(7) . . . . ?
C14 C9 N1 C16 -61.9(7) . . . . ?
C14 C9 N1 C17 84.8(7) . . . . ?
C14 C13 C15 C16 54.6(7) . . . . ?
C15 C13 C14 C8 66.4(6) . . . . ?
C15 C13 C14 C9 -59.2(6) . . . . ?
C15 C13 C14 C19 -179.8(5) . . . . ?
C15 C16 N1 C9 54.2(7) . . . . ?
C15 C16 N1 C17 -92.1(7) . . . . ?
C18 C6 C7 C8 54.0(6) . . . . ?
C18 C6 C7 C20 -70.0(6) . . . . ?
C18 C6 O3 C23 -51.7(8) . . . . ?
C20 C7 C8 C14 130.6(5) . . . . ?
N1 C9 C10 C11 -96.5(6) . . . . ?
N1 C9 C14 C8 -58.4(7) . . . . ?
N1 C9 C14 C13 61.5(6) . . . . ?
N1 C9 C14 C19 179.8(5) . . . . ?
O1 C4 C12 C11 162.9(6) . . . . ?
O1 C4 C12 C13 -3.7(8) . . . . ?
O1 C5 C6 C7 -178.4(4) . . . . ?
O1 C5 C6 C18 66.8(6) . . . . ?
O1 C5 C6 O3 -62.6(6) . . . . ?
O1 C5 C13 C12 -13.1(6) . . . . ?
O1 C5 C13 C14 -124.5(5) . . . . ?
O1 C5 C13 C15 109.7(6) . . . . ?
O2 C3 C4 C12 -179.0(6) . . . . ?
O2 C3 C4 O1 8.0(10) . . . . ?
O3 C6 C7 C8 177.3(5) . . . . ?
O3 C6 C7 C20 53.3(7) . . . . ?
O3 C6 C18 C19 -177.6(5) . . . . ?
O4 C20 C21 F1 53.2(8) . . . . ?
O4 C20 C21 F2 -67.1(7) . . . . ?
O4 C20 C21 F3 171.9(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.775(3)
2 0.225(3)

