# 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. 
# 
#######################################################################

data_30
_database_code_depnum_ccdc_archive 'CCDC 2291933'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-09-15 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H27 F2 N O4'
_chemical_formula_sum            'C23 H27 F2 N O4'
_chemical_formula_weight         419.45
_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                   8.7371(4)
_cell_length_b                   13.1143(5)
_cell_length_c                   8.7598(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.946(3)
_cell_angle_gamma                90
_cell_volume                     954.87(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2519
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.13
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1149 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.9229.
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    1.459
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0821
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11851
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_min         2.444
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3566
_reflns_number_total             4617
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1346 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         4617
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.026
_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)+(0.0514P)²+0.2772P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1279
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2. Restrained distances
 O4'-C20' \\sim O4-C20
 with sigma of 0.02
 F1'-C21 \\sim F1-C21
 with sigma of 0.02
 F2-C21 \\sim F2'-C21
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C20) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C20') \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O4) = Uanis(O4')
Uanis(C20') = Uanis(C20)
Uanis(F2) = Uanis(F2')
Uanis(F1) = Uanis(F1')
4. Others
 Sof(H7A)=Sof(H21A)=Sof(F1')=Sof(F2')=Sof(O4')=Sof(C20')=Sof(H20')=1-FVAR(1)
 Sof(H7B)=Sof(H21)=Sof(F1)=Sof(F2)=Sof(O4)=Sof(C20)=Sof(H20)=FVAR(1)
5.a Riding coordinates:
 O4(H4)
5.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7A), C7(H7B), C9(H9), C21(H21A), C21(H21), C20(H20), C20'(H20')
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C18(H18), C19(H19)
5.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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
O1 O -0.1060(3) 0.3294(2) 0.9758(3) 0.0204(7) Uani 1 1 d . . . . .
O2 O 0.1579(3) 0.4127(2) 0.9304(3) 0.0188(6) Uani 1 1 d . . . . .
O3 O 0.4290(3) 0.3971(2) 1.0107(3) 0.0208(7) Uani 1 1 d . . . . .
N1 N 0.0720(4) 0.5734(3) 0.3099(4) 0.0178(7) Uani 1 1 d . . . . .
C1 C -0.2344(5) 0.3640(3) 0.5357(5) 0.0189(9) Uani 1 1 d . . . . .
H1 H -0.3183 0.3441 0.4425 0.023 Uiso 1 1 calc R U . . .
C2 C -0.2467(5) 0.3413(3) 0.6873(5) 0.0188(9) Uani 1 1 d . . . . .
H2 H -0.3432 0.3129 0.6974 0.023 Uiso 1 1 calc R U . . .
C3 C -0.1175(5) 0.3604(3) 0.8232(5) 0.0170(8) Uani 1 1 d . . . . .
C4 C 0.0152(5) 0.4124(3) 0.8046(5) 0.0155(8) Uani 1 1 d . . . . .
C5 C 0.2987(5) 0.5205(3) 0.7949(5) 0.0143(8) Uani 1 1 d . . . . .
H5 H 0.2894 0.5774 0.8675 0.017 Uiso 1 1 calc R U . . .
C6 C 0.2999(5) 0.4172(3) 0.8740(5) 0.0171(8) Uani 1 1 d . . . . .
C7 C 0.4464(5) 0.5356(3) 0.7329(5) 0.0164(8) Uani 1 1 d . . . . .
H7A H 0.5303 0.4835 0.7834 0.020 Uiso 0.352(5) 1 calc R U P A 1
H7B H 0.5151 0.4745 0.7748 0.020 Uiso 0.648(5) 1 calc R U P A 2
C8 C 0.3818(5) 0.5166(3) 0.5489(5) 0.0172(8) Uani 1 1 d . . . . .
H8A H 0.3638 0.5818 0.4889 0.021 Uiso 1 1 calc R U . . .
H8B H 0.4576 0.4742 0.5124 0.021 Uiso 1 1 calc R U . . .
C9 C 0.0951(5) 0.4656(3) 0.3601(5) 0.0166(8) Uani 1 1 d . . . . .
H9 H 0.1385 0.4288 0.2824 0.020 Uiso 1 1 calc R U . . .
C10 C -0.0613(5) 0.4112(3) 0.3618(5) 0.0177(8) Uani 1 1 d . . . . .
H10A H -0.1522 0.4417 0.2768 0.021 Uiso 1 1 calc R U . . .
H10B H -0.0537 0.3387 0.3333 0.021 Uiso 1 1 calc R U . . .
C11 C -0.1012(5) 0.4152(3) 0.5195(5) 0.0165(8) Uani 1 1 d . . . . .
C12 C 0.0139(5) 0.4511(3) 0.6577(5) 0.0151(8) Uani 1 1 d . . . . .
C13 C 0.1511(5) 0.5162(3) 0.6436(5) 0.0150(8) Uani 1 1 d . . . . .
C14 C 0.2238(5) 0.4607(3) 0.5270(5) 0.0164(8) Uani 1 1 d . . . . .
C15 C 0.0941(5) 0.6242(3) 0.5860(4) 0.0150(8) Uani 1 1 d . . . . .
H15A H 0.0296 0.6511 0.6523 0.018 Uiso 1 1 calc R U . . .
H15B H 0.1893 0.6688 0.6033 0.018 Uiso 1 1 calc R U . . .
C16 C -0.0068(5) 0.6297(3) 0.4093(4) 0.0175(8) Uani 1 1 d . . . . .
H16A H -0.1146 0.6004 0.3956 0.021 Uiso 1 1 calc R U . . .
H16B H -0.0209 0.7019 0.3746 0.021 Uiso 1 1 calc R U . . .
C17 C -0.0185(6) 0.5851(4) 0.1406(5) 0.0239(10) Uani 1 1 d . . . . .
H17A H -0.1269 0.5570 0.1206 0.036 Uiso 1 1 calc R U . . .
H17B H 0.0366 0.5486 0.0752 0.036 Uiso 1 1 calc R U . . .
H17C H -0.0262 0.6576 0.1122 0.036 Uiso 1 1 calc R U . . .
C18 C 0.2998(5) 0.3347(3) 0.7522(5) 0.0192(9) Uani 1 1 d . . . . .
H18 H 0.3257 0.2668 0.7892 0.023 Uiso 1 1 calc R U . . .
C19 C 0.2650(5) 0.3535(3) 0.5957(5) 0.0182(8) Uani 1 1 d . . . . .
H19 H 0.2657 0.2987 0.5249 0.022 Uiso 1 1 calc R U . . .
C21 C 0.6900(5) 0.6388(4) 0.7390(5) 0.0240(9) Uani 1 1 d D . . . .
H21A H 0.7529 0.5740 0.7654 0.029 Uiso 0.352(5) 1 calc R U P A 2
H21 H 0.7606 0.5850 0.8058 0.029 Uiso 0.648(5) 1 calc R U P A 1
C22 C -0.2364(5) 0.2690(3) 0.9911(5) 0.0227(10) Uani 1 1 d . . . . .
H22A H -0.2515 0.2098 0.9197 0.034 Uiso 1 1 calc R U . . .
H22B H -0.3349 0.3100 0.9620 0.034 Uiso 1 1 calc R U . . .
H22C H -0.2122 0.2457 1.1023 0.034 Uiso 1 1 calc R U . . .
C23 C 0.4543(5) 0.4720(4) 1.1376(5) 0.0254(10) Uani 1 1 d . . . . .
H23A H 0.3527 0.4843 1.1602 0.038 Uiso 1 1 calc R U . . .
H23B H 0.4924 0.5358 1.1038 0.038 Uiso 1 1 calc R U . . .
H23C H 0.5348 0.4465 1.2347 0.038 Uiso 1 1 calc R U . . .
F1 F 0.7549(10) 0.7364(5) 0.7731(9) 0.0323(17) Uani 0.648(5) 1 d D . P A 1
F2 F 0.671(3) 0.6280(15) 0.5800(13) 0.028(3) Uani 0.648(5) 1 d D . P A 1
O4 O 0.5447(5) 0.6700(3) 0.9255(5) 0.0210(9) Uani 0.648(5) 1 d D . P A 1
H4 H 0.5067 0.7402 0.8907 0.025 Uiso 1 1 d R U . . .
C20 C 0.5219(8) 0.6424(5) 0.7616(8) 0.0151(13) Uani 0.648(5) 1 d D U P A 1
H20 H 0.4516 0.6931 0.6871 0.018 Uiso 0.648(5) 1 calc R U P A 1
F1' F 0.794(2) 0.7126(12) 0.815(2) 0.0323(17) Uani 0.352(5) 1 d D . P A 2
F2' F 0.655(7) 0.649(3) 0.579(2) 0.028(3) Uani 0.352(5) 1 d D . P A 2
O4' O 0.4665(10) 0.7161(6) 0.7703(10) 0.0210(9) Uani 0.352(5) 1 d D . P A 2
C20' C 0.5563(16) 0.6254(10) 0.8044(16) 0.0151(13) Uani 0.352(5) 1 d D U P A 2
H20' H 0.6000 0.6166 0.9234 0.018 Uiso 0.352(5) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.371(5) . ?
O1 C22 1.427(5) . ?
O2 C4 1.387(5) . ?
O2 C6 1.470(5) . ?
O3 C6 1.394(5) . ?
O3 C23 1.448(5) . ?
N1 C9 1.476(5) . ?
N1 C16 1.465(5) . ?
N1 C17 1.458(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.397(6) . ?
C1 C11 1.389(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(5) . ?
C3 C4 1.397(5) . ?
C4 C12 1.380(6) . ?
C5 H5 1.0000 . ?
C5 C6 1.520(6) . ?
C5 C7 1.560(6) . ?
C5 C13 1.539(5) . ?
C6 C18 1.520(6) . ?
C7 H7A 1.0000 . ?
C7 H7B 1.0000 . ?
C7 C8 1.555(5) . ?
C7 C20 1.535(8) . ?
C7 C20' 1.526(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.522(6) . ?
C9 H9 1.0000 . ?
C9 C10 1.546(6) . ?
C9 C14 1.547(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.526(5) . ?
C11 C12 1.396(6) . ?
C12 C13 1.508(6) . ?
C13 C14 1.541(5) . ?
C13 C15 1.534(5) . ?
C14 C19 1.528(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.528(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.332(6) . ?
C19 H19 0.9500 . ?
C21 H21A 1.0000 . ?
C21 H21 1.0000 . ?
C21 F1 1.394(8) . ?
C21 F2 1.358(11) . ?
C21 C20 1.542(8) . ?
C21 F1' 1.355(15) . ?
C21 F2' 1.347(19) . ?
C21 C20' 1.462(15) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
O4 H4 0.9936 . ?
O4 C20 1.434(8) . ?
C20 H20 1.0000 . ?
O4' H4 1.0517 . ?
O4' C20' 1.405(14) . ?
C20' H20' 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C22 115.8(3) . . ?
C4 O2 C6 112.2(3) . . ?
C6 O3 C23 115.0(3) . . ?
C16 N1 C9 110.6(3) . . ?
C17 N1 C9 112.7(3) . . ?
C17 N1 C16 110.2(3) . . ?
C2 C1 H1 119.6 . . ?
C11 C1 H1 119.6 . . ?
C11 C1 C2 120.8(4) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
O1 C3 C2 125.3(4) . . ?
O1 C3 C4 116.4(3) . . ?
C2 C3 C4 118.2(4) . . ?
O2 C4 C3 118.9(3) . . ?
C12 C4 O2 119.2(3) . . ?
C12 C4 C3 121.3(3) . . ?
C6 C5 H5 111.4 . . ?
C6 C5 C7 112.5(3) . . ?
C6 C5 C13 104.3(3) . . ?
C7 C5 H5 111.4 . . ?
C13 C5 H5 111.4 . . ?
C13 C5 C7 105.6(3) . . ?
O2 C6 C5 107.5(3) . . ?
O2 C6 C18 112.9(3) . . ?
O3 C6 O2 104.3(3) . . ?
O3 C6 C5 116.8(3) . . ?
O3 C6 C18 107.0(3) . . ?
C5 C6 C18 108.4(3) . . ?
C5 C7 H7A 109.4 . . ?
C5 C7 H7B 103.7 . . ?
C8 C7 C5 105.4(3) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 103.7 . . ?
C20 C7 C5 114.8(4) . . ?
C20 C7 H7A 109.4 . . ?
C20 C7 C8 108.4(4) . . ?
C20' C7 C5 116.0(6) . . ?
C20' C7 H7B 103.7 . . ?
C20' C7 C8 122.0(6) . . ?
C7 C8 H8A 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.0 . . ?
C14 C8 C7 103.5(3) . . ?
C14 C8 H8A 111.1 . . ?
C14 C8 H8B 111.1 . . ?
N1 C9 H9 107.8 . . ?
N1 C9 C10 113.9(3) . . ?
N1 C9 C14 108.3(3) . . ?
C10 C9 H9 107.8 . . ?
C10 C9 C14 111.1(3) . . ?
C14 C9 H9 107.8 . . ?
C9 C10 H10A 108.2 . . ?
C9 C10 H10B 108.2 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 116.2(3) . . ?
C11 C10 H10A 108.2 . . ?
C11 C10 H10B 108.2 . . ?
C1 C11 C10 120.5(4) . . ?
C1 C11 C12 118.5(4) . . ?
C12 C11 C10 119.5(4) . . ?
C4 C12 C11 118.8(4) . . ?
C4 C12 C13 120.4(3) . . ?
C11 C12 C13 119.9(4) . . ?
C5 C13 C14 100.4(3) . . ?
C12 C13 C5 115.2(3) . . ?
C12 C13 C14 106.7(3) . . ?
C12 C13 C15 111.3(3) . . ?
C15 C13 C5 110.5(3) . . ?
C15 C13 C14 112.1(3) . . ?
C8 C14 C9 117.8(3) . . ?
C8 C14 C13 103.4(3) . . ?
C8 C14 C19 107.4(3) . . ?
C13 C14 C9 106.2(3) . . ?
C19 C14 C9 115.1(3) . . ?
C19 C14 C13 105.6(3) . . ?
C13 C15 H15A 108.8 . . ?
C13 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C13 113.8(3) . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
N1 C16 C15 110.3(3) . . ?
N1 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C18 H18 118.6 . . ?
C19 C18 C6 122.7(4) . . ?
C19 C18 H18 118.6 . . ?
C14 C19 H19 119.1 . . ?
C18 C19 C14 121.8(4) . . ?
C18 C19 H19 119.1 . . ?
F1 C21 H21 112.7 . . ?
F1 C21 C20 106.6(6) . . ?
F2 C21 H21 112.7 . . ?
F2 C21 F1 103.3(12) . . ?
F2 C21 C20 108.2(13) . . ?
C20 C21 H21 112.7 . . ?
F1' C21 H21A 104.8 . . ?
F1' C21 C20' 112.9(11) . . ?
F2' C21 H21A 104.8 . . ?
F2' C21 F1' 110(3) . . ?
F2' C21 C20' 118(3) . . ?
C20' C21 H21A 104.8 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 O4 H4 89.8 . . ?
C7 C20 C21 109.2(5) . . ?
C7 C20 H20 110.7 . . ?
C21 C20 H20 110.7 . . ?
O4 C20 C7 108.3(5) . . ?
O4 C20 C21 107.0(5) . . ?
O4 C20 H20 110.7 . . ?
C20' O4' H4 92.8 . . ?
C7 C20' H20' 109.2 . . ?
C21 C20' C7 114.2(9) . . ?
C21 C20' H20' 109.2 . . ?
O4' C20' C7 109.0(9) . . ?
O4' C20' C21 106.0(10) . . ?
O4' C20' H20' 109.2 . . ?

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 C3 C4 O2 12.0(5) . . . . ?
O1 C3 C4 C12 -177.1(4) . . . . ?
O2 C4 C12 C11 153.8(4) . . . . ?
O2 C4 C12 C13 -15.4(6) . . . . ?
O2 C6 C18 C19 104.5(4) . . . . ?
O3 C6 C18 C19 -141.3(4) . . . . ?
N1 C9 C10 C11 -90.7(4) . . . . ?
N1 C9 C14 C8 -50.5(5) . . . . ?
N1 C9 C14 C13 64.8(4) . . . . ?
N1 C9 C14 C19 -178.8(3) . . . . ?
C1 C2 C3 O1 -170.8(4) . . . . ?
C1 C2 C3 C4 7.0(6) . . . . ?
C1 C11 C12 C4 17.0(6) . . . . ?
C1 C11 C12 C13 -173.8(4) . . . . ?
C2 C1 C11 C10 160.8(4) . . . . ?
C2 C1 C11 C12 -5.3(6) . . . . ?
C2 C3 C4 O2 -165.9(4) . . . . ?
C2 C3 C4 C12 5.0(6) . . . . ?
C3 C4 C12 C11 -17.1(6) . . . . ?
C3 C4 C12 C13 173.7(4) . . . . ?
C4 O2 C6 O3 -168.9(3) . . . . ?
C4 O2 C6 C5 66.5(4) . . . . ?
C4 O2 C6 C18 -53.1(4) . . . . ?
C4 C12 C13 C5 9.4(5) . . . . ?
C4 C12 C13 C14 119.9(4) . . . . ?
C4 C12 C13 C15 -117.4(4) . . . . ?
C5 C6 C18 C19 -14.6(5) . . . . ?
C5 C7 C8 C14 -17.3(4) . . . . ?
C5 C7 C20 C21 164.5(4) . . . . ?
C5 C7 C20 O4 48.3(6) . . . . ?
C5 C7 C20' C21 -178.0(6) . . . . ?
C5 C7 C20' O4' -59.6(11) . . . . ?
C5 C13 C14 C8 -46.8(4) . . . . ?
C5 C13 C14 C9 -171.4(3) . . . . ?
C5 C13 C14 C19 65.9(4) . . . . ?
C5 C13 C15 C16 158.5(3) . . . . ?
C6 O2 C4 C3 148.6(4) . . . . ?
C6 O2 C4 C12 -22.5(5) . . . . ?
C6 C5 C7 C8 101.5(4) . . . . ?
C6 C5 C7 C20 -139.3(4) . . . . ?
C6 C5 C7 C20' -120.2(7) . . . . ?
C6 C5 C13 C12 30.8(4) . . . . ?
C6 C5 C13 C14 -83.4(3) . . . . ?
C6 C5 C13 C15 158.0(3) . . . . ?
C6 C18 C19 C14 0.6(6) . . . . ?
C7 C5 C6 O2 178.8(3) . . . . ?
C7 C5 C6 O3 62.0(5) . . . . ?
C7 C5 C6 C18 -58.9(4) . . . . ?
C7 C5 C13 C12 149.5(3) . . . . ?
C7 C5 C13 C14 35.3(4) . . . . ?
C7 C5 C13 C15 -83.3(4) . . . . ?
C7 C8 C14 C9 156.7(3) . . . . ?
C7 C8 C14 C13 40.0(4) . . . . ?
C7 C8 C14 C19 -71.3(4) . . . . ?
C8 C7 C20 C21 -78.0(5) . . . . ?
C8 C7 C20 O4 165.8(4) . . . . ?
C8 C7 C20' C21 -47.2(11) . . . . ?
C8 C7 C20' O4' 71.2(10) . . . . ?
C8 C14 C19 C18 82.3(5) . . . . ?
C9 N1 C16 C15 58.9(4) . . . . ?
C9 C10 C11 C1 -176.5(4) . . . . ?
C9 C10 C11 C12 -10.5(6) . . . . ?
C9 C14 C19 C18 -144.4(4) . . . . ?
C10 C9 C14 C8 -176.2(4) . . . . ?
C10 C9 C14 C13 -61.0(4) . . . . ?
C10 C9 C14 C19 55.4(5) . . . . ?
C10 C11 C12 C4 -149.3(4) . . . . ?
C10 C11 C12 C13 20.0(6) . . . . ?
C11 C1 C2 C3 -6.8(6) . . . . ?
C11 C12 C13 C5 -159.7(4) . . . . ?
C11 C12 C13 C14 -49.1(5) . . . . ?
C11 C12 C13 C15 73.5(5) . . . . ?
C12 C13 C14 C8 -167.3(3) . . . . ?
C12 C13 C14 C9 68.0(4) . . . . ?
C12 C13 C14 C19 -54.6(4) . . . . ?
C12 C13 C15 C16 -72.1(4) . . . . ?
C13 C5 C6 O2 -67.4(4) . . . . ?
C13 C5 C6 O3 175.9(3) . . . . ?
C13 C5 C6 C18 55.0(4) . . . . ?
C13 C5 C7 C8 -11.5(4) . . . . ?
C13 C5 C7 C20 107.7(4) . . . . ?
C13 C5 C7 C20' 126.7(6) . . . . ?
C13 C14 C19 C18 -27.6(5) . . . . ?
C13 C15 C16 N1 -47.9(5) . . . . ?
C14 C9 C10 C11 31.9(5) . . . . ?
C14 C13 C15 C16 47.4(5) . . . . ?
C15 C13 C14 C8 70.5(4) . . . . ?
C15 C13 C14 C9 -54.1(4) . . . . ?
C15 C13 C14 C19 -176.8(3) . . . . ?
C16 N1 C9 C10 54.7(4) . . . . ?
C16 N1 C9 C14 -69.3(4) . . . . ?
C17 N1 C9 C10 -69.0(4) . . . . ?
C17 N1 C9 C14 166.9(3) . . . . ?
C17 N1 C16 C15 -175.9(3) . . . . ?
C22 O1 C3 C2 2.8(6) . . . . ?
C22 O1 C3 C4 -175.0(4) . . . . ?
C23 O3 C6 O2 -63.7(4) . . . . ?
C23 O3 C6 C5 54.8(5) . . . . ?
C23 O3 C6 C18 176.5(3) . . . . ?
F1 C21 C20 C7 -177.5(5) . . . . ?
F1 C21 C20 O4 -60.5(6) . . . . ?
F2 C21 C20 C7 72.0(10) . . . . ?
F2 C21 C20 O4 -171.0(10) . . . . ?
C20 C7 C8 C14 -140.6(4) . . . . ?
F1' C21 C20' C7 -174.0(9) . . . . ?
F1' C21 C20' O4' 65.9(12) . . . . ?
F2' C21 C20' C7 56(2) . . . . ?
F2' C21 C20' O4' -65(2) . . . . ?
C20' C7 C8 C14 -152.4(6) . . . . ?

_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_34
_database_code_depnum_ccdc_archive 'CCDC 2291934'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-09-11 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H29 F2 N O4, C H4 O'
_chemical_formula_sum            'C25 H33 F2 N O5'
_chemical_formula_weight         465.52
_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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   40.487(3)
_cell_length_b                   7.3959(4)
_cell_length_c                   7.5817(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.636(7)
_cell_angle_gamma                90
_cell_volume                     2259.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6129
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1436 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.7853.
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    1.369
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0713
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20675
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.990
_diffrn_reflns_theta_min         2.022
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                4773
_reflns_number_total             5921
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 1721 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5921
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0729
_refine_ls_restrained_S_all      1.072
_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)+(0.0558P)²+5.6167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1559
_refine_ls_wR_factor_ref         0.1674
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2. Restrained distances
 O4'-C20 \\sim O4-C20
 with sigma of 0.02
 C22-C20 \\sim C22'-C20
 with sigma of 0.02
 F2'-C21' \\sim F2-C21
 with sigma of 0.02
 F1'-C21' \\sim F1-C21
 with sigma of 0.02
 O1-C23 \\sim O1-C23'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O2S) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O4') = Uanis(O4)
Uanis(C22') = Uanis(C22)
Uanis(F1') = Uanis(F1)
Uanis(C21) = Uanis(C21')
Uanis(F2') = Uanis(F2)
Uanis(C23) = Uanis(C23')
4. Others
 Sof(F1)=Sof(F2)=Sof(O4)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22A)=Sof(H22B)=
 Sof(H22C)=1-FVAR(1)
 Sof(F1')=Sof(F2')=Sof(O4')=Sof(C21')=Sof(H21')=Sof(C22')=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=FVAR(1)
 Sof(C23')=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(2)
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(2)
 Fixed Sof: O1S(0.5) H1S(0.5) C1S(0.5) H1SA(0.5) H1SB(0.5) H1SC(0.5) O2S(0.5)
 H2S(0.5) C2S(0.5) H2SA(0.5) H2SB(0.5) H2SC(0.5)
5.a Riding coordinates:
 O4(H4), O1S(H1S), O2S(H2S)
5.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C21(H21), C21'(H21')
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C18(H18), C19(H19)
5.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C22'(H22D,H22E,H22F), C23'(H23D,H23E,H23F), C1S(H1SA,H1SB,H1SC),
 C2S(H2SA,H2SB,H2SC)
;
_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
O1 O 0.26573(10) 0.7231(5) 0.8111(5) 0.0321(9) Uani 1 1 d D . . . .
O2 O 0.32136(8) 0.5251(4) 0.7766(4) 0.0219(7) Uani 1 1 d . . . . .
O3 O 0.35039(9) 0.2670(5) 0.8406(4) 0.0243(7) Uani 1 1 d . . . . .
N1 N 0.39666(10) 0.7746(5) 0.2375(5) 0.0200(8) Uani 1 1 d . . . . .
C1 C 0.28709(12) 0.8545(6) 0.3631(7) 0.0241(10) Uani 1 1 d . . . . .
H1 H 0.2773 0.9120 0.2587 0.029 Uiso 1 1 calc R U . . .
C2 C 0.26996(13) 0.8510(6) 0.5143(7) 0.0266(11) Uani 1 1 d . . . . .
H2 H 0.2501 0.9188 0.5165 0.032 Uiso 1 1 calc R U . . .
C3 C 0.28171(12) 0.7491(6) 0.6618(6) 0.0236(10) Uani 1 1 d . . . . .
C4 C 0.31226(13) 0.6618(6) 0.6565(6) 0.0211(9) Uani 1 1 d . . . . .
C5 C 0.37680(11) 0.4994(6) 0.6931(5) 0.0168(9) Uani 1 1 d . . . . .
H5 H 0.3847 0.5619 0.8065 0.020 Uiso 1 1 calc R U . . .
C6 C 0.34530(12) 0.3976(6) 0.7086(6) 0.0193(9) Uani 1 1 d . . . . .
C7 C 0.40468(11) 0.3750(6) 0.6267(6) 0.0178(8) Uani 1 1 d . . . . .
H7 H 0.3966 0.2474 0.6297 0.021 Uiso 1 1 calc R U . . .
C8 C 0.40621(11) 0.4268(6) 0.4278(6) 0.0175(9) Uani 1 1 d . . . . .
H8A H 0.4247 0.5113 0.4136 0.021 Uiso 1 1 calc R U . . .
H8B H 0.4088 0.3182 0.3541 0.021 Uiso 1 1 calc R U . . .
C9 C 0.36902(12) 0.6443(6) 0.2165(5) 0.0172(9) Uani 1 1 d . . . . .
H9 H 0.3716 0.5695 0.1089 0.021 Uiso 1 1 calc R U . . .
C10 C 0.33420(12) 0.7336(6) 0.1940(6) 0.0217(10) Uani 1 1 d . . . . .
H10A H 0.3359 0.8480 0.1279 0.026 Uiso 1 1 calc R U . . .
H10B H 0.3191 0.6529 0.1196 0.026 Uiso 1 1 calc R U . . .
C11 C 0.31815(12) 0.7752(6) 0.3634(6) 0.0209(9) Uani 1 1 d . . . . .
C12 C 0.33228(12) 0.6978(6) 0.5236(6) 0.0190(9) Uani 1 1 d . . . . .
C13 C 0.36776(12) 0.6370(6) 0.5409(5) 0.0157(8) Uani 1 1 d . . . . .
C14 C 0.37233(11) 0.5183(6) 0.3794(5) 0.0150(8) Uani 1 1 d . . . . .
C15 C 0.39128(12) 0.8018(6) 0.5555(5) 0.0181(9) Uani 1 1 d . . . . .
H15A H 0.3841 0.8862 0.6455 0.022 Uiso 1 1 calc R U . . .
H15B H 0.4140 0.7603 0.5969 0.022 Uiso 1 1 calc R U . . .
C16 C 0.39229(13) 0.9026(6) 0.3812(6) 0.0211(10) Uani 1 1 d . . . . .
H16A H 0.3714 0.9707 0.3538 0.025 Uiso 1 1 calc R U . . .
H16B H 0.4109 0.9902 0.3916 0.025 Uiso 1 1 calc R U . . .
C17 C 0.40119(13) 0.8711(7) 0.0723(6) 0.0268(11) Uani 1 1 d . . . . .
H17A H 0.3807 0.9351 0.0311 0.040 Uiso 1 1 calc R U . . .
H17B H 0.4066 0.7842 -0.0182 0.040 Uiso 1 1 calc R U . . .
H17C H 0.4194 0.9584 0.0937 0.040 Uiso 1 1 calc R U . . .
C18 C 0.33332(12) 0.3198(6) 0.5261(6) 0.0188(9) Uani 1 1 d . . . . .
H18 H 0.3164 0.2305 0.5176 0.023 Uiso 1 1 calc R U . . .
C19 C 0.34586(11) 0.3734(5) 0.3800(5) 0.0160(8) Uani 1 1 d . . . . .
H19 H 0.3379 0.3186 0.2706 0.019 Uiso 1 1 calc R U . . .
C20 C 0.43820(12) 0.3834(6) 0.7416(6) 0.0219(9) Uani 1 1 d D . . . .
C24 C 0.32243(14) 0.1539(7) 0.8601(7) 0.0274(11) Uani 1 1 d . . . . .
H24A H 0.3220 0.1212 0.9851 0.041 Uiso 1 1 calc R U . . .
H24B H 0.3241 0.0439 0.7893 0.041 Uiso 1 1 calc R U . . .
H24C H 0.3020 0.2187 0.8192 0.041 Uiso 1 1 calc R U . . .
F1 F 0.4569(5) 0.108(2) 0.618(3) 0.048(4) Uani 0.60(3) 1 d D . P A 1
F2 F 0.4957(7) 0.283(7) 0.740(5) 0.037(4) Uani 0.60(3) 1 d D . P A 1
O4 O 0.4467(5) 0.5697(15) 0.754(3) 0.019(3) Uani 0.60(3) 1 d D . P A 1
H4 H 0.4681 0.5928 0.8186 0.023 Uiso 1 1 d R U . . .
C21 C 0.4652(8) 0.288(3) 0.644(5) 0.030(4) Uani 0.60(3) 1 d D . P A 1
H21 H 0.4671 0.3478 0.5274 0.036 Uiso 0.60(3) 1 calc R U P A 1
C22 C 0.4349(9) 0.330(3) 0.934(2) 0.027(4) Uani 0.60(3) 1 d D . P A 1
H22A H 0.4199 0.4148 0.9860 0.041 Uiso 0.60(3) 1 calc R U P A 1
H22B H 0.4568 0.3348 1.0020 0.041 Uiso 0.60(3) 1 calc R U P A 1
H22C H 0.4260 0.2075 0.9382 0.041 Uiso 0.60(3) 1 calc R U P A 1
C23 C 0.2417(7) 0.859(3) 0.846(4) 0.032(4) Uani 0.72(12) 1 d D . P B 1
H23A H 0.2516 0.9790 0.8385 0.049 Uiso 0.72(12) 1 calc R U P B 1
H23B H 0.2347 0.8405 0.9648 0.049 Uiso 0.72(12) 1 calc R U P B 1
H23C H 0.2223 0.8488 0.7579 0.049 Uiso 0.72(12) 1 calc R U P B 1
F1' F 0.4505(8) 0.081(4) 0.670(4) 0.048(4) Uani 0.40(3) 1 d D . P A 2
F2' F 0.4910(12) 0.271(11) 0.764(8) 0.037(4) Uani 0.40(3) 1 d D . P A 2
O4' O 0.4540(6) 0.555(3) 0.737(5) 0.019(3) Uani 0.40(3) 1 d D . P A 2
C21' C 0.4609(13) 0.258(5) 0.664(9) 0.030(4) Uani 0.40(3) 1 d D . P A 2
H21' H 0.4634 0.2936 0.5387 0.036 Uiso 0.40(3) 1 calc R U P A 2
C22' C 0.4358(16) 0.287(5) 0.920(3) 0.027(4) Uani 0.40(3) 1 d D . P A 2
H22D H 0.4144 0.3145 0.9638 0.041 Uiso 0.40(3) 1 calc R U P A 2
H22E H 0.4539 0.3280 1.0061 0.041 Uiso 0.40(3) 1 calc R U P A 2
H22F H 0.4377 0.1557 0.9031 0.041 Uiso 0.40(3) 1 calc R U P A 2
C23' C 0.2365(11) 0.833(9) 0.820(9) 0.032(4) Uani 0.28(12) 1 d D . P B 2
H23D H 0.2176 0.7757 0.7505 0.049 Uiso 0.28(12) 1 calc R U P B 2
H23E H 0.2403 0.9530 0.7716 0.049 Uiso 0.28(12) 1 calc R U P B 2
H23F H 0.2317 0.8441 0.9436 0.049 Uiso 0.28(12) 1 calc R U P B 2
O1S O 0.46577(19) 0.6882(11) 0.2669(9) 0.0318(17) Uani 0.5 1 d . . P C -1
H1S H 0.4424 0.7173 0.2483 0.038 Uiso 0.5 1 d R U P . .
C1S C 0.4830(3) 0.7943(17) 0.4020(15) 0.038(3) Uani 0.5 1 d . . P C -1
H1SA H 0.4786 0.7478 0.5183 0.058 Uiso 0.5 1 calc R U P C -1
H1SB H 0.4756 0.9201 0.3901 0.058 Uiso 0.5 1 calc R U P C -1
H1SC H 0.5069 0.7882 0.3908 0.058 Uiso 0.5 1 calc R U P C -1
O2S O 0.5002(10) 0.6594(8) -0.003(5) 0.0268(16) Uani 0.5 1 d . U P D -1
H2S H 0.5077 0.6598 -0.1082 0.032 Uiso 0.5 1 d R U P D -1
C2S C 0.4949(3) 0.8408(16) 0.0652(16) 0.041(3) Uani 0.5 1 d . . P D -1
H2SA H 0.4933 0.8344 0.1932 0.061 Uiso 0.5 1 calc R U P D -1
H2SB H 0.4742 0.8908 0.0063 0.061 Uiso 0.5 1 calc R U P D -1
H2SC H 0.5135 0.9188 0.0418 0.061 Uiso 0.5 1 calc R U P D -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.371(6) . ?
O1 C23 1.441(10) . ?
O1 C23' 1.44(2) . ?
O2 C4 1.386(5) . ?
O2 C6 1.481(5) . ?
O3 C6 1.392(5) . ?
O3 C24 1.427(6) . ?
N1 C9 1.473(6) . ?
N1 C16 1.467(6) . ?
N1 C17 1.469(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.397(7) . ?
C1 C11 1.387(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(7) . ?
C3 C4 1.399(7) . ?
C4 C12 1.380(7) . ?
C5 H5 1.0000 . ?
C5 C6 1.496(6) . ?
C5 C7 1.576(6) . ?
C5 C13 1.555(6) . ?
C6 C18 1.533(6) . ?
C7 H7 1.0000 . ?
C7 C8 1.563(6) . ?
C7 C20 1.541(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.541(6) . ?
C9 H9 1.0000 . ?
C9 C10 1.551(7) . ?
C9 C14 1.543(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.527(6) . ?
C11 C12 1.412(6) . ?
C12 C13 1.499(7) . ?
C13 C14 1.533(6) . ?
C13 C15 1.544(6) . ?
C14 C19 1.516(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.521(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.324(6) . ?
C19 H19 0.9500 . ?
C20 O4 1.421(11) . ?
C20 C21 1.55(4) . ?
C20 C22 1.531(13) . ?
C20 O4' 1.425(17) . ?
C20 C21' 1.47(6) . ?
C20 C22' 1.540(18) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
F1 C21 1.381(15) . ?
F2 C21 1.373(13) . ?
O4 H4 0.9655 . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
F1' C21' 1.380(19) . ?
F2' C21' 1.373(19) . ?
O4' H4 0.8464 . ?
C21' H21' 1.0000 . ?
C22' H22D 0.9800 . ?
C22' H22E 0.9800 . ?
C22' H22F 0.9800 . ?
C23' H23D 0.9800 . ?
C23' H23E 0.9800 . ?
C23' H23F 0.9800 . ?
O1S H1S 0.9659 . ?
O1S C1S 1.418(13) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
O2S H2S 0.8794 . ?
O2S C2S 1.46(2) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 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
C3 O1 C23 115.9(10) . . ?
C3 O1 C23' 115(3) . . ?
C4 O2 C6 112.1(3) . . ?
C6 O3 C24 114.7(4) . . ?
C16 N1 C9 110.9(4) . . ?
C16 N1 C17 110.7(3) . . ?
C17 N1 C9 112.5(3) . . ?
C2 C1 H1 119.6 . . ?
C11 C1 H1 119.6 . . ?
C11 C1 C2 120.9(4) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.7(5) . . ?
C3 C2 H2 119.6 . . ?
O1 C3 C2 125.9(5) . . ?
O1 C3 C4 116.7(4) . . ?
C2 C3 C4 117.4(5) . . ?
O2 C4 C3 119.8(4) . . ?
C12 C4 O2 118.9(4) . . ?
C12 C4 C3 121.1(4) . . ?
C6 C5 H5 111.5 . . ?
C6 C5 C7 112.0(3) . . ?
C6 C5 C13 104.3(3) . . ?
C7 C5 H5 111.5 . . ?
C13 C5 H5 111.5 . . ?
C13 C5 C7 105.6(3) . . ?
O2 C6 C5 107.4(3) . . ?
O2 C6 C18 113.2(4) . . ?
O3 C6 O2 104.3(3) . . ?
O3 C6 C5 109.8(4) . . ?
O3 C6 C18 113.6(4) . . ?
C5 C6 C18 108.4(4) . . ?
C5 C7 H7 107.3 . . ?
C8 C7 C5 105.2(3) . . ?
C8 C7 H7 107.3 . . ?
C20 C7 C5 114.5(4) . . ?
C20 C7 H7 107.3 . . ?
C20 C7 C8 114.8(4) . . ?
C7 C8 H8A 111.2 . . ?
C7 C8 H8B 111.2 . . ?
H8A C8 H8B 109.2 . . ?
C14 C8 C7 102.6(3) . . ?
C14 C8 H8A 111.2 . . ?
C14 C8 H8B 111.2 . . ?
N1 C9 H9 108.1 . . ?
N1 C9 C10 114.0(4) . . ?
N1 C9 C14 107.7(3) . . ?
C10 C9 H9 108.1 . . ?
C14 C9 H9 108.1 . . ?
C14 C9 C10 110.6(4) . . ?
C9 C10 H10A 108.1 . . ?
C9 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
C11 C10 C9 116.8(4) . . ?
C11 C10 H10A 108.1 . . ?
C11 C10 H10B 108.1 . . ?
C1 C11 C10 123.0(4) . . ?
C1 C11 C12 117.6(4) . . ?
C12 C11 C10 118.2(4) . . ?
C4 C12 C11 119.3(4) . . ?
C4 C12 C13 120.3(4) . . ?
C11 C12 C13 120.1(4) . . ?
C12 C13 C5 114.5(4) . . ?
C12 C13 C14 107.0(3) . . ?
C12 C13 C15 110.4(4) . . ?
C14 C13 C5 100.3(3) . . ?
C14 C13 C15 112.8(4) . . ?
C15 C13 C5 111.4(3) . . ?
C8 C14 C9 117.5(4) . . ?
C13 C14 C8 103.6(3) . . ?
C13 C14 C9 106.6(3) . . ?
C19 C14 C8 107.6(3) . . ?
C19 C14 C9 115.1(3) . . ?
C19 C14 C13 105.2(3) . . ?
C13 C15 H15A 108.9 . . ?
C13 C15 H15B 108.9 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C13 113.2(4) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
N1 C16 C15 110.1(3) . . ?
N1 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C18 H18 119.0 . . ?
C19 C18 C6 122.0(4) . . ?
C19 C18 H18 119.0 . . ?
C14 C19 H19 118.6 . . ?
C18 C19 C14 122.9(4) . . ?
C18 C19 H19 118.6 . . ?
C7 C20 C21 109.6(13) . . ?
C7 C20 C22' 111(2) . . ?
O4 C20 C7 105.7(9) . . ?
O4 C20 C21 107.3(8) . . ?
O4 C20 C22 103.1(14) . . ?
C22 C20 C7 112.1(15) . . ?
C22 C20 C21 118.0(17) . . ?
O4' C20 C7 113.2(15) . . ?
O4' C20 C21' 104.5(16) . . ?
O4' C20 C22' 120(2) . . ?
C21' C20 C7 107(2) . . ?
C21' C20 C22' 99(3) . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 O4 H4 113.9 . . ?
C20 C21 H21 109.8 . . ?
F1 C21 C20 109.4(18) . . ?
F1 C21 H21 109.8 . . ?
F2 C21 C20 113(3) . . ?
F2 C21 F1 104(3) . . ?
F2 C21 H21 109.8 . . ?
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 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 O4' H4 123.1 . . ?
C20 C21' H21' 109.9 . . ?
F1' C21' C20 112(4) . . ?
F1' C21' H21' 109.9 . . ?
F2' C21' C20 107(5) . . ?
F2' C21' F1' 108(5) . . ?
F2' C21' H21' 109.9 . . ?
C20 C22' H22D 109.5 . . ?
C20 C22' H22E 109.5 . . ?
C20 C22' H22F 109.5 . . ?
H22D C22' H22E 109.5 . . ?
H22D C22' H22F 109.5 . . ?
H22E C22' H22F 109.5 . . ?
O1 C23' H23D 109.5 . . ?
O1 C23' H23E 109.5 . . ?
O1 C23' H23F 109.5 . . ?
H23D C23' H23E 109.5 . . ?
H23D C23' H23F 109.5 . . ?
H23E C23' H23F 109.5 . . ?
C1S O1S H1S 112.8 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C2S O2S H2S 113.2 . . ?
O2S C2S H2SA 109.5 . . ?
O2S C2S H2SB 109.5 . . ?
O2S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 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 C3 C4 O2 14.6(6) . . . . ?
O1 C3 C4 C12 -171.4(4) . . . . ?
O2 C4 C12 C11 153.5(4) . . . . ?
O2 C4 C12 C13 -19.8(6) . . . . ?
O2 C6 C18 C19 105.7(5) . . . . ?
O3 C6 C18 C19 -135.6(4) . . . . ?
N1 C9 C10 C11 -88.3(5) . . . . ?
N1 C9 C14 C8 -51.4(5) . . . . ?
N1 C9 C14 C13 64.2(4) . . . . ?
N1 C9 C14 C19 -179.6(4) . . . . ?
C1 C2 C3 O1 -174.2(4) . . . . ?
C1 C2 C3 C4 4.4(7) . . . . ?
C1 C11 C12 C4 16.4(6) . . . . ?
C1 C11 C12 C13 -170.2(4) . . . . ?
C2 C1 C11 C10 164.5(4) . . . . ?
C2 C1 C11 C12 -2.5(7) . . . . ?
C2 C3 C4 O2 -164.1(4) . . . . ?
C2 C3 C4 C12 9.8(7) . . . . ?
C3 C4 C12 C11 -20.5(6) . . . . ?
C3 C4 C12 C13 166.1(4) . . . . ?
C4 O2 C6 O3 -177.4(3) . . . . ?
C4 O2 C6 C5 66.1(4) . . . . ?
C4 O2 C6 C18 -53.4(5) . . . . ?
C4 C12 C13 C5 12.9(6) . . . . ?
C4 C12 C13 C14 123.1(4) . . . . ?
C4 C12 C13 C15 -113.8(4) . . . . ?
C5 C6 C18 C19 -13.4(6) . . . . ?
C5 C7 C8 C14 -19.8(4) . . . . ?
C5 C7 C20 O4 -53.3(10) . . . . ?
C5 C7 C20 C21 -168.6(9) . . . . ?
C5 C7 C20 C22 58.3(10) . . . . ?
C5 C7 C20 O4' -66.2(15) . . . . ?
C5 C7 C20 C21' 178.9(17) . . . . ?
C5 C7 C20 C22' 72.1(16) . . . . ?
C5 C13 C14 C8 -47.5(4) . . . . ?
C5 C13 C14 C9 -172.1(4) . . . . ?
C5 C13 C14 C19 65.3(4) . . . . ?
C5 C13 C15 C16 158.7(4) . . . . ?
C6 O2 C4 C3 154.7(4) . . . . ?
C6 O2 C4 C12 -19.4(5) . . . . ?
C6 C5 C7 C8 103.9(4) . . . . ?
C6 C5 C7 C20 -129.0(4) . . . . ?
C6 C5 C13 C12 30.1(5) . . . . ?
C6 C5 C13 C14 -84.0(4) . . . . ?
C6 C5 C13 C15 156.4(4) . . . . ?
C6 C18 C19 C14 -1.5(7) . . . . ?
C7 C5 C6 O2 178.3(3) . . . . ?
C7 C5 C6 O3 65.5(4) . . . . ?
C7 C5 C6 C18 -59.1(4) . . . . ?
C7 C5 C13 C12 148.3(4) . . . . ?
C7 C5 C13 C14 34.2(4) . . . . ?
C7 C5 C13 C15 -85.5(4) . . . . ?
C7 C8 C14 C9 159.5(3) . . . . ?
C7 C8 C14 C13 42.3(4) . . . . ?
C7 C8 C14 C19 -68.8(4) . . . . ?
C7 C20 C21 F1 -62(2) . . . . ?
C7 C20 C21 F2 -178(2) . . . . ?
C7 C20 C21' F1' -64(4) . . . . ?
C7 C20 C21' F2' 178(3) . . . . ?
C8 C7 C20 O4 68.6(10) . . . . ?
C8 C7 C20 C21 -46.7(10) . . . . ?
C8 C7 C20 C22 -179.7(10) . . . . ?
C8 C7 C20 O4' 55.7(15) . . . . ?
C8 C7 C20 C21' -59.2(17) . . . . ?
C8 C7 C20 C22' -166.0(16) . . . . ?
C8 C14 C19 C18 83.6(5) . . . . ?
C9 N1 C16 C15 60.3(5) . . . . ?
C9 C10 C11 C1 -179.9(4) . . . . ?
C9 C10 C11 C12 -12.9(6) . . . . ?
C9 C14 C19 C18 -143.4(4) . . . . ?
C10 C9 C14 C8 -176.5(4) . . . . ?
C10 C9 C14 C13 -60.9(4) . . . . ?
C10 C9 C14 C19 55.3(5) . . . . ?
C10 C11 C12 C4 -151.2(4) . . . . ?
C10 C11 C12 C13 22.2(6) . . . . ?
C11 C1 C2 C3 -7.9(7) . . . . ?
C11 C12 C13 C5 -160.4(4) . . . . ?
C11 C12 C13 C14 -50.2(5) . . . . ?
C11 C12 C13 C15 72.9(5) . . . . ?
C12 C13 C14 C8 -167.3(3) . . . . ?
C12 C13 C14 C9 68.1(4) . . . . ?
C12 C13 C14 C19 -54.5(4) . . . . ?
C12 C13 C15 C16 -72.9(5) . . . . ?
C13 C5 C6 O2 -68.0(4) . . . . ?
C13 C5 C6 O3 179.2(3) . . . . ?
C13 C5 C6 C18 54.6(4) . . . . ?
C13 C5 C7 C8 -9.0(4) . . . . ?
C13 C5 C7 C20 118.0(4) . . . . ?
C13 C14 C19 C18 -26.4(5) . . . . ?
C13 C15 C16 N1 -47.8(5) . . . . ?
C14 C9 C10 C11 33.2(5) . . . . ?
C14 C13 C15 C16 46.7(5) . . . . ?
C15 C13 C14 C8 71.1(4) . . . . ?
C15 C13 C14 C9 -53.5(5) . . . . ?
C15 C13 C14 C19 -176.1(4) . . . . ?
C16 N1 C9 C10 53.2(5) . . . . ?
C16 N1 C9 C14 -69.9(4) . . . . ?
C17 N1 C9 C10 -71.5(5) . . . . ?
C17 N1 C9 C14 165.4(4) . . . . ?
C17 N1 C16 C15 -174.0(4) . . . . ?
C20 C7 C8 C14 -146.6(4) . . . . ?
C24 O3 C6 O2 68.8(4) . . . . ?
C24 O3 C6 C5 -176.4(4) . . . . ?
C24 O3 C6 C18 -54.9(5) . . . . ?
O4 C20 C21 F1 -176(2) . . . . ?
O4 C20 C21 F2 68(3) . . . . ?
C22 C20 C21 F1 68(3) . . . . ?
C22 C20 C21 F2 -48(3) . . . . ?
C23 O1 C3 C2 -23(2) . . . . ?
C23 O1 C3 C4 158.1(19) . . . . ?
O4' C20 C21' F1' 175(4) . . . . ?
O4' C20 C21' F2' 58(4) . . . . ?
C22' C20 C21' F1' 51(5) . . . . ?
C22' C20 C21' F2' -67(4) . . . . ?
C23' O1 C3 C2 -9(3) . . . . ?
C23' O1 C3 C4 173(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_40
_database_code_depnum_ccdc_archive 'CCDC 2291935'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-09-12 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H26 F2 N2 O4'
_chemical_formula_sum            'C23 H26 F2 N2 O4'
_chemical_formula_weight         432.46
_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      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                   7.7726(4)
_cell_length_b                   11.5067(6)
_cell_length_c                   22.6755(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2028.03(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5815
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.52
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1535 before and 0.0828 after correction.
The Ratio of minimum to maximum transmission is 0.8477.
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    1.416
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            26533
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         1.985
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                4287
_reflns_number_total             5347
_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         0.361
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 
;
 Flack x determined using 1518 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5347
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0673
_refine_ls_restrained_S_all      1.074
_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)+(0.0528P)²+1.8343P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1573
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2. Restrained distances
 N1-C17 \\sim N1-C17'
 with sigma of 0.02
 N2-C17 \\sim N2'-C17'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N2) = Uanis(N2')
Uanis(C17) = Uanis(C17')
4. Others
 Sof(N2')=Sof(C17')=1-FVAR(1)
 Sof(N2)=Sof(C17)=FVAR(1)
5.a Riding coordinates:
 O4(H4)
5.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C20(H20), C21(H21)
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B),
 C19(H19A,H19B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
5.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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
F1 F 0.7721(4) 0.4605(3) 0.27189(14) 0.0520(10) Uani 1 1 d . . . . .
F2 F 0.7082(5) 0.3100(4) 0.21807(14) 0.0570(11) Uani 1 1 d . . . . .
O1 O 0.4893(4) 0.4575(3) 0.61907(13) 0.0279(7) Uani 1 1 d . . . . .
O2 O 0.5286(3) 0.5035(2) 0.49811(12) 0.0161(6) Uani 1 1 d . . . . .
O3 O 0.6665(3) 0.3668(2) 0.39529(13) 0.0182(6) Uani 1 1 d . . . . .
O4 O 0.4180(5) 0.2669(3) 0.28984(15) 0.0312(8) Uani 1 1 d . . . . .
H4 H 0.3340 0.2617 0.2563 0.037 Uiso 1 1 d R U . . .
N1 N 0.0256(5) 0.6817(3) 0.37424(17) 0.0226(8) Uani 1 1 d D . . . .
C1 C 0.0451(6) 0.5297(3) 0.56934(19) 0.0228(9) Uani 1 1 d . . . . .
H1 H -0.0696 0.5279 0.5837 0.027 Uiso 1 1 calc R U . . .
C2 C 0.1802(6) 0.5031(4) 0.60760(19) 0.0235(9) Uani 1 1 d . . . . .
H2 H 0.1565 0.4902 0.6482 0.028 Uiso 1 1 calc R U . . .
C3 C 0.3502(6) 0.4950(3) 0.58733(18) 0.0201(8) Uani 1 1 d . . . . .
C4 C 0.3774(5) 0.5225(3) 0.52880(17) 0.0164(8) Uani 1 1 d . . . . .
C5 C 0.4913(5) 0.5236(3) 0.43530(17) 0.0146(7) Uani 1 1 d . . . . .
H5 H 0.5759 0.5807 0.4191 0.018 Uiso 1 1 calc R U . . .
C6 C 0.4950(5) 0.4127(3) 0.39760(18) 0.0147(7) Uani 1 1 d . . . . .
C7 C 0.4547(5) 0.4586(3) 0.33482(17) 0.0176(8) Uani 1 1 d . . . . .
H7 H 0.5263 0.5299 0.3290 0.021 Uiso 1 1 calc R U . . .
C8 C 0.2626(5) 0.4973(4) 0.33033(18) 0.0194(8) Uani 1 1 d . . . . .
H8A H 0.2549 0.5745 0.3112 0.023 Uiso 1 1 calc R U . . .
H8B H 0.1968 0.4410 0.3063 0.023 Uiso 1 1 calc R U . . .
C9 C 0.0090(5) 0.5615(3) 0.39846(19) 0.0204(8) Uani 1 1 d . . . . .
H9 H -0.0751 0.5174 0.3737 0.025 Uiso 1 1 calc R U . . .
C10 C -0.0597(5) 0.5665(4) 0.4628(2) 0.0218(9) Uani 1 1 d . . . . .
H10A H -0.1239 0.6401 0.4679 0.026 Uiso 1 1 calc R U . . .
H10B H -0.1425 0.5020 0.4684 0.026 Uiso 1 1 calc R U . . .
C11 C 0.0746(5) 0.5589(3) 0.51078(18) 0.0176(8) Uani 1 1 d . . . . .
C12 C 0.2467(5) 0.5618(3) 0.49382(18) 0.0165(8) Uani 1 1 d . . . . .
C13 C 0.3083(5) 0.5762(3) 0.43200(17) 0.0142(7) Uani 1 1 d . . . . .
C14 C 0.1874(5) 0.5033(3) 0.39279(17) 0.0160(7) Uani 1 1 d . . . . .
C15 C 0.1409(6) 0.7607(4) 0.40761(19) 0.0215(9) Uani 1 1 d . . . . .
H15A H 0.0937 0.7748 0.4475 0.026 Uiso 1 1 calc R U . . .
H15B H 0.1506 0.8363 0.3870 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3162(5) 0.7036(3) 0.41206(18) 0.0177(8) Uani 1 1 d . . . . .
H16A H 0.3876 0.7479 0.4404 0.021 Uiso 1 1 calc R U . . .
H16B H 0.3732 0.7075 0.3731 0.021 Uiso 1 1 calc R U . . .
C18 C 0.3620(5) 0.3260(3) 0.41987(18) 0.0161(7) Uani 1 1 d . . . . .
H18A H 0.3857 0.3072 0.4617 0.019 Uiso 1 1 calc R U . . .
H18B H 0.3702 0.2532 0.3968 0.019 Uiso 1 1 calc R U . . .
C19 C 0.1795(5) 0.3765(3) 0.41415(18) 0.0166(8) Uani 1 1 d . . . . .
H19A H 0.1122 0.3295 0.3858 0.020 Uiso 1 1 calc R U . . .
H19B H 0.1208 0.3731 0.4529 0.020 Uiso 1 1 calc R U . . .
C20 C 0.4962(6) 0.3764(4) 0.28337(19) 0.0227(9) Uani 1 1 d . . . . .
H20 H 0.4477 0.4124 0.2468 0.027 Uiso 1 1 calc R U . . .
C21 C 0.6857(7) 0.3580(5) 0.2728(2) 0.0347(12) Uani 1 1 d . . . . .
H21 H 0.7347 0.3058 0.3038 0.042 Uiso 1 1 calc R U . . .
C22 C 0.4594(8) 0.4286(5) 0.6796(2) 0.0418(14) Uani 1 1 d . . . . .
H22A H 0.3735 0.3664 0.6820 0.063 Uiso 1 1 calc R U . . .
H22B H 0.4171 0.4973 0.7007 0.063 Uiso 1 1 calc R U . . .
H22C H 0.5671 0.4022 0.6977 0.063 Uiso 1 1 calc R U . . .
C23 C 0.7163(5) 0.2917(4) 0.4426(2) 0.0217(9) Uani 1 1 d . . . . .
H23A H 0.8374 0.2697 0.4378 0.033 Uiso 1 1 calc R U . . .
H23B H 0.6445 0.2217 0.4421 0.033 Uiso 1 1 calc R U . . .
H23C H 0.7013 0.3322 0.4802 0.033 Uiso 1 1 calc R U . . .
N2 N -0.212(3) 0.7515(11) 0.3116(11) 0.051(5) Uani 0.74(6) 1 d D . P A 1
C17 C -0.100(3) 0.719(3) 0.3410(10) 0.031(4) Uani 0.74(6) 1 d D . P A 1
N2' N -0.154(7) 0.754(4) 0.2948(19) 0.051(5) Uani 0.26(6) 1 d D . P A 2
C17' C -0.071(8) 0.727(8) 0.334(3) 0.031(4) Uani 0.26(6) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C21 1.357(6) . ?
F2 C21 1.370(5) . ?
O1 C3 1.369(5) . ?
O1 C22 1.432(6) . ?
O2 C4 1.383(5) . ?
O2 C5 1.472(5) . ?
O3 C6 1.434(5) . ?
O3 C23 1.430(5) . ?
O4 H4 1.0041 . ?
O4 C20 1.406(5) . ?
N1 C9 1.494(5) . ?
N1 C15 1.483(5) . ?
N1 C17 1.305(9) . ?
N1 C17' 1.29(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.396(6) . ?
C1 C11 1.389(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.402(6) . ?
C3 C4 1.381(5) . ?
C4 C12 1.366(6) . ?
C5 H5 1.0000 . ?
C5 C6 1.536(5) . ?
C5 C13 1.547(5) . ?
C6 C7 1.550(6) . ?
C6 C18 1.523(5) . ?
C7 H7 1.0000 . ?
C7 C8 1.562(6) . ?
C7 C20 1.536(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.533(6) . ?
C9 H9 1.0000 . ?
C9 C10 1.556(6) . ?
C9 C14 1.545(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.510(6) . ?
C11 C12 1.392(5) . ?
C12 C13 1.491(5) . ?
C13 C14 1.542(5) . ?
C13 C16 1.536(5) . ?
C14 C19 1.538(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.516(6) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.539(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20 1.0000 . ?
C20 C21 1.507(7) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
N2 C17 1.156(10) . ?
N2' C17' 1.14(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C22 116.7(4) . . ?
C4 O2 C5 107.1(3) . . ?
C23 O3 C6 116.5(3) . . ?
C20 O4 H4 104.8 . . ?
C15 N1 C9 115.6(3) . . ?
C17 N1 C9 116.7(14) . . ?
C17 N1 C15 123.1(15) . . ?
C17' N1 C9 126(4) . . ?
C17' N1 C15 118(5) . . ?
C2 C1 H1 119.2 . . ?
C11 C1 H1 119.2 . . ?
C11 C1 C2 121.5(4) . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.3(4) . . ?
C3 C2 H2 119.4 . . ?
O1 C3 C2 126.4(4) . . ?
O1 C3 C4 117.2(4) . . ?
C4 C3 C2 116.4(4) . . ?
C3 C4 O2 125.3(4) . . ?
C12 C4 O2 113.1(3) . . ?
C12 C4 C3 121.3(4) . . ?
O2 C5 H5 109.2 . . ?
O2 C5 C6 113.9(3) . . ?
O2 C5 C13 106.8(3) . . ?
C6 C5 H5 109.2 . . ?
C6 C5 C13 108.4(3) . . ?
C13 C5 H5 109.2 . . ?
O3 C6 C5 110.1(3) . . ?
O3 C6 C7 106.2(3) . . ?
O3 C6 C18 113.7(3) . . ?
C5 C6 C7 103.0(3) . . ?
C18 C6 C5 110.3(3) . . ?
C18 C6 C7 113.0(3) . . ?
C6 C7 H7 106.8 . . ?
C6 C7 C8 110.5(3) . . ?
C8 C7 H7 106.8 . . ?
C20 C7 C6 116.4(3) . . ?
C20 C7 H7 106.8 . . ?
C20 C7 C8 109.1(3) . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C14 C8 C7 108.5(3) . . ?
C14 C8 H8A 110.0 . . ?
C14 C8 H8B 110.0 . . ?
N1 C9 H9 108.7 . . ?
N1 C9 C10 109.9(3) . . ?
N1 C9 C14 107.1(3) . . ?
C10 C9 H9 108.7 . . ?
C14 C9 H9 108.7 . . ?
C14 C9 C10 113.7(3) . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 115.8(3) . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C1 C11 C10 126.0(4) . . ?
C1 C11 C12 115.4(4) . . ?
C12 C11 C10 117.7(4) . . ?
C4 C12 C11 123.1(4) . . ?
C4 C12 C13 110.1(3) . . ?
C11 C12 C13 124.8(4) . . ?
C12 C13 C5 101.9(3) . . ?
C12 C13 C14 106.6(3) . . ?
C12 C13 C16 113.3(3) . . ?
C14 C13 C5 112.0(3) . . ?
C16 C13 C5 110.6(3) . . ?
C16 C13 C14 112.0(3) . . ?
C8 C14 C9 116.0(3) . . ?
C8 C14 C13 108.9(3) . . ?
C8 C14 C19 105.3(3) . . ?
C13 C14 C9 105.2(3) . . ?
C19 C14 C9 110.4(3) . . ?
C19 C14 C13 111.0(3) . . ?
N1 C15 H15A 110.1 . . ?
N1 C15 H15B 110.1 . . ?
N1 C15 C16 108.1(3) . . ?
H15A C15 H15B 108.4 . . ?
C16 C15 H15A 110.1 . . ?
C16 C15 H15B 110.1 . . ?
C13 C16 H16A 108.9 . . ?
C13 C16 H16B 108.9 . . ?
C15 C16 C13 113.4(3) . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C6 C18 H18A 109.6 . . ?
C6 C18 H18B 109.6 . . ?
C6 C18 C19 110.5(3) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
C14 C19 C18 110.4(3) . . ?
C14 C19 H19A 109.6 . . ?
C14 C19 H19B 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
O4 C20 C7 112.4(3) . . ?
O4 C20 H20 107.2 . . ?
O4 C20 C21 108.3(4) . . ?
C7 C20 H20 107.2 . . ?
C21 C20 C7 114.3(4) . . ?
C21 C20 H20 107.2 . . ?
F1 C21 F2 105.8(4) . . ?
F1 C21 C20 111.4(4) . . ?
F1 C21 H21 110.2 . . ?
F2 C21 C20 109.0(4) . . ?
F2 C21 H21 110.2 . . ?
C20 C21 H21 110.2 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C17 N1 180(3) . . ?
N2' C17' N1 172(10) . . ?

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 C3 C4 O2 7.4(6) . . . . ?
O1 C3 C4 C12 -179.3(3) . . . . ?
O2 C4 C12 C11 163.1(4) . . . . ?
O2 C4 C12 C13 -1.6(4) . . . . ?
O2 C5 C6 O3 -66.4(4) . . . . ?
O2 C5 C6 C7 -179.3(3) . . . . ?
O2 C5 C6 C18 59.9(4) . . . . ?
O2 C5 C13 C12 -9.4(4) . . . . ?
O2 C5 C13 C14 -123.1(3) . . . . ?
O2 C5 C13 C16 111.3(3) . . . . ?
O3 C6 C7 C8 173.3(3) . . . . ?
O3 C6 C7 C20 48.2(4) . . . . ?
O3 C6 C18 C19 -173.3(3) . . . . ?
O4 C20 C21 F1 -174.0(4) . . . . ?
O4 C20 C21 F2 69.6(5) . . . . ?
N1 C9 C10 C11 -97.5(4) . . . . ?
N1 C9 C14 C8 -57.7(4) . . . . ?
N1 C9 C14 C13 62.8(4) . . . . ?
N1 C9 C14 C19 -177.3(3) . . . . ?
N1 C15 C16 C13 -48.1(5) . . . . ?
C1 C2 C3 O1 -172.5(4) . . . . ?
C1 C2 C3 C4 4.3(6) . . . . ?
C1 C11 C12 C4 9.5(6) . . . . ?
C1 C11 C12 C13 171.9(4) . . . . ?
C2 C1 C11 C10 167.4(4) . . . . ?
C2 C1 C11 C12 -1.3(6) . . . . ?
C2 C3 C4 O2 -169.7(3) . . . . ?
C2 C3 C4 C12 3.7(6) . . . . ?
C3 C4 C12 C11 -11.0(6) . . . . ?
C3 C4 C12 C13 -175.7(3) . . . . ?
C4 O2 C5 C6 -110.6(3) . . . . ?
C4 O2 C5 C13 8.9(4) . . . . ?
C4 C12 C13 C5 6.9(4) . . . . ?
C4 C12 C13 C14 124.5(3) . . . . ?
C4 C12 C13 C16 -111.9(4) . . . . ?
C5 O2 C4 C3 169.0(4) . . . . ?
C5 O2 C4 C12 -4.8(4) . . . . ?
C5 C6 C7 C8 -71.0(4) . . . . ?
C5 C6 C7 C20 163.9(3) . . . . ?
C5 C6 C18 C19 62.5(4) . . . . ?
C5 C13 C14 C8 -59.5(4) . . . . ?
C5 C13 C14 C9 175.5(3) . . . . ?
C5 C13 C14 C19 56.0(4) . . . . ?
C5 C13 C16 C15 179.8(3) . . . . ?
C6 C5 C13 C12 113.7(3) . . . . ?
C6 C5 C13 C14 0.0(4) . . . . ?
C6 C5 C13 C16 -125.6(3) . . . . ?
C6 C7 C8 C14 12.7(4) . . . . ?
C6 C7 C20 O4 54.2(5) . . . . ?
C6 C7 C20 C21 -69.7(5) . . . . ?
C6 C18 C19 C14 -5.0(5) . . . . ?
C7 C6 C18 C19 -52.1(4) . . . . ?
C7 C8 C14 C9 169.2(3) . . . . ?
C7 C8 C14 C13 50.7(4) . . . . ?
C7 C8 C14 C19 -68.4(4) . . . . ?
C7 C20 C21 F1 -47.9(6) . . . . ?
C7 C20 C21 F2 -164.2(4) . . . . ?
C8 C7 C20 O4 -71.6(4) . . . . ?
C8 C7 C20 C21 164.4(4) . . . . ?
C8 C14 C19 C18 65.0(4) . . . . ?
C9 N1 C15 C16 55.7(5) . . . . ?
C9 C10 C11 C1 -161.1(4) . . . . ?
C9 C10 C11 C12 7.3(5) . . . . ?
C9 C14 C19 C18 -169.1(3) . . . . ?
C10 C9 C14 C8 -179.2(3) . . . . ?
C10 C9 C14 C13 -58.8(4) . . . . ?
C10 C9 C14 C19 61.1(4) . . . . ?
C10 C11 C12 C4 -160.2(4) . . . . ?
C10 C11 C12 C13 2.2(6) . . . . ?
C11 C1 C2 C3 -5.5(6) . . . . ?
C11 C12 C13 C5 -157.5(4) . . . . ?
C11 C12 C13 C14 -39.9(5) . . . . ?
C11 C12 C13 C16 83.7(5) . . . . ?
C12 C13 C14 C8 -170.2(3) . . . . ?
C12 C13 C14 C9 64.8(4) . . . . ?
C12 C13 C14 C19 -54.7(4) . . . . ?
C12 C13 C16 C15 -66.5(4) . . . . ?
C13 C5 C6 O3 174.9(3) . . . . ?
C13 C5 C6 C7 62.0(4) . . . . ?
C13 C5 C6 C18 -58.8(4) . . . . ?
C13 C14 C19 C18 -52.8(4) . . . . ?
C14 C9 C10 C11 22.5(5) . . . . ?
C14 C13 C16 C15 54.1(5) . . . . ?
C15 N1 C9 C10 58.7(4) . . . . ?
C15 N1 C9 C14 -65.3(4) . . . . ?
C16 C13 C14 C8 65.3(4) . . . . ?
C16 C13 C14 C9 -59.7(4) . . . . ?
C16 C13 C14 C19 -179.1(3) . . . . ?
C18 C6 C7 C8 48.0(4) . . . . ?
C18 C6 C7 C20 -77.1(4) . . . . ?
C20 C7 C8 C14 141.9(3) . . . . ?
C22 O1 C3 C2 -3.0(6) . . . . ?
C22 O1 C3 C4 -179.7(4) . . . . ?
C23 O3 C6 C5 85.7(4) . . . . ?
C23 O3 C6 C7 -163.6(3) . . . . ?
C23 O3 C6 C18 -38.6(5) . . . . ?
C17 N1 C9 C10 -98.2(16) . . . . ?
C17 N1 C9 C14 137.9(15) . . . . ?
C17 N1 C15 C16 -149.1(15) . . . . ?
C17' N1 C9 C10 -109(5) . . . . ?
C17' N1 C9 C14 127(5) . . . . ?
C17' N1 C15 C16 -135(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_33
_database_code_depnum_ccdc_archive 'CCDC 2291936'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-09-12 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H29 F2 N O4, C H4 O'
_chemical_formula_sum            'C25 H33 F2 N O5'
_chemical_formula_weight         465.52
_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      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                   7.7954(2)
_cell_length_b                   12.3806(2)
_cell_length_c                   23.4227(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2260.57(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1144 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.9168.
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    1.368
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            30248
_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         28.996
_diffrn_reflns_theta_min         1.861
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.765
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5816
_reflns_number_total             6003
_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         0.426
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 2464 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         6003
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+0.5148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0894
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Riding coordinates:
 O4(H4), O1S(H1S)
2.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C21(H21)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C18(H18), C19(H19)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C1S(H1SA,H1SB,H1SC)
;
_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
F1 F 0.94783(16) 0.64678(10) 0.52907(5) 0.0287(3) Uani 1 1 d . . . . .
F2 F 1.06535(17) 0.49393(11) 0.50602(6) 0.0350(3) Uani 1 1 d . . . . .
O1 O 1.03815(15) 0.37851(10) 0.27489(5) 0.0149(2) Uani 1 1 d . . . . .
O2 O 1.10208(16) 0.40859(11) 0.15626(5) 0.0195(3) Uani 1 1 d . . . . .
O3 O 1.05823(16) 0.53781(11) 0.37146(5) 0.0173(2) Uani 1 1 d . . . . .
O4 O 0.70813(17) 0.49259(11) 0.50880(5) 0.0182(3) Uani 1 1 d . . . . .
H4 H 0.7524 0.4310 0.5179 0.022 Uiso 1 1 d R U . . .
N1 N 0.45759(18) 0.20696(11) 0.34598(6) 0.0137(3) Uani 1 1 d . . . . .
C1 C 0.6378(2) 0.33855(13) 0.16269(7) 0.0145(3) Uani 1 1 d . . . . .
H1 H 0.5401 0.3361 0.1385 0.017 Uiso 1 1 calc R U . . .
C2 C 0.7984(2) 0.36373(14) 0.13945(6) 0.0152(3) Uani 1 1 d . . . . .
H2 H 0.8090 0.3732 0.0994 0.018 Uiso 1 1 calc R U . . .
C3 C 0.9438(2) 0.37531(13) 0.17406(7) 0.0147(3) Uani 1 1 d . . . . .
C4 C 0.9215(2) 0.35512(13) 0.23228(7) 0.0132(3) Uani 1 1 d . . . . .
C5 C 0.9455(2) 0.37038(13) 0.32925(6) 0.0118(3) Uani 1 1 d . . . . .
H5 H 1.0146 0.3256 0.3563 0.014 Uiso 1 1 calc R U . . .
C6 C 0.9058(2) 0.48062(12) 0.35770(6) 0.0115(3) Uani 1 1 d . . . . .
C7 C 0.8178(2) 0.44850(13) 0.41548(6) 0.0114(3) Uani 1 1 d . . . . .
H7 H 0.8906 0.3906 0.4328 0.014 Uiso 1 1 calc R U . . .
C8 C 0.6395(2) 0.39612(13) 0.40303(6) 0.0121(3) Uani 1 1 d . . . . .
H8A H 0.6302 0.3262 0.4233 0.014 Uiso 1 1 calc R U . . .
H8B H 0.5469 0.4441 0.4170 0.014 Uiso 1 1 calc R U . . .
C9 C 0.4589(2) 0.31513(13) 0.31822(6) 0.0122(3) Uani 1 1 d . . . . .
H9 H 0.3559 0.3554 0.3322 0.015 Uiso 1 1 calc R U . . .
C10 C 0.4477(2) 0.31021(14) 0.25148(6) 0.0149(3) Uani 1 1 d . . . . .
H10A H 0.3908 0.2418 0.2405 0.018 Uiso 1 1 calc R U . . .
H10B H 0.3742 0.3703 0.2381 0.018 Uiso 1 1 calc R U . . .
C11 C 0.6186(2) 0.31695(12) 0.22090(6) 0.0129(3) Uani 1 1 d . . . . .
C12 C 0.7678(2) 0.31885(13) 0.25304(6) 0.0120(3) Uani 1 1 d . . . . .
C13 C 0.7758(2) 0.31211(13) 0.31681(6) 0.0109(3) Uani 1 1 d . . . . .
C14 C 0.6195(2) 0.37799(12) 0.33809(6) 0.0106(3) Uani 1 1 d . . . . .
C15 C 0.7727(2) 0.19613(13) 0.34007(7) 0.0137(3) Uani 1 1 d . . . . .
H15A H 0.8674 0.1543 0.3226 0.016 Uiso 1 1 calc R U . . .
H15B H 0.7914 0.1977 0.3819 0.016 Uiso 1 1 calc R U . . .
C16 C 0.6032(2) 0.14037(13) 0.32741(7) 0.0159(3) Uani 1 1 d . . . . .
H16A H 0.5941 0.1265 0.2859 0.019 Uiso 1 1 calc R U . . .
H16B H 0.5996 0.0699 0.3474 0.019 Uiso 1 1 calc R U . . .
C17 C 0.2968(2) 0.14800(14) 0.33597(8) 0.0184(3) Uani 1 1 d . . . . .
H17A H 0.1993 0.1942 0.3460 0.028 Uiso 1 1 calc R U . . .
H17B H 0.2948 0.0827 0.3596 0.028 Uiso 1 1 calc R U . . .
H17C H 0.2891 0.1278 0.2956 0.028 Uiso 1 1 calc R U . . .
C18 C 0.7780(2) 0.54195(13) 0.32198(7) 0.0131(3) Uani 1 1 d . . . . .
H18 H 0.8001 0.6124 0.3076 0.016 Uiso 1 1 calc R U . . .
C19 C 0.6317(2) 0.48971(13) 0.31206(6) 0.0127(3) Uani 1 1 d . . . . .
H19 H 0.5413 0.5204 0.2902 0.015 Uiso 1 1 calc R U . . .
C20 C 0.7988(2) 0.53831(13) 0.46186(7) 0.0148(3) Uani 1 1 d . . . . .
C21 C 0.9729(3) 0.57781(16) 0.48419(8) 0.0224(4) Uani 1 1 d . . . . .
H21 H 1.0386 0.6146 0.4531 0.027 Uiso 1 1 calc R U . . .
C22 C 1.1191(3) 0.43085(16) 0.09656(7) 0.0222(4) Uani 1 1 d . . . . .
H22A H 1.0899 0.3660 0.0746 0.033 Uiso 1 1 calc R U . . .
H22B H 1.2376 0.4520 0.0882 0.033 Uiso 1 1 calc R U . . .
H22C H 1.0414 0.4897 0.0860 0.033 Uiso 1 1 calc R U . . .
C23 C 1.1559(2) 0.58123(15) 0.32516(7) 0.0186(3) Uani 1 1 d . . . . .
H23A H 1.0810 0.6249 0.3007 0.028 Uiso 1 1 calc R U . . .
H23B H 1.2052 0.5220 0.3028 0.028 Uiso 1 1 calc R U . . .
H23C H 1.2484 0.6266 0.3403 0.028 Uiso 1 1 calc R U . . .
C24 C 0.6985(3) 0.63733(15) 0.44297(8) 0.0224(4) Uani 1 1 d . . . . .
H24A H 0.5873 0.6148 0.4275 0.034 Uiso 1 1 calc R U . . .
H24B H 0.7632 0.6759 0.4135 0.034 Uiso 1 1 calc R U . . .
H24C H 0.6802 0.6851 0.4758 0.034 Uiso 1 1 calc R U . . .
O1S O 0.35853(19) 0.20483(11) 0.46241(6) 0.0251(3) Uani 1 1 d . . . . .
H1S H 0.4125 0.2171 0.4261 0.030 Uiso 1 1 d R U . . .
C1S C 0.2717(3) 0.30255(18) 0.47351(9) 0.0279(4) Uani 1 1 d . . . . .
H1SA H 0.2504 0.3405 0.4375 0.042 Uiso 1 1 calc R U . . .
H1SB H 0.3422 0.3480 0.4984 0.042 Uiso 1 1 calc R U . . .
H1SC H 0.1621 0.2871 0.4923 0.042 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 1.368(2) . ?
F2 C21 1.363(2) . ?
O1 C4 1.3808(18) . ?
O1 C5 1.4673(18) . ?
O2 C3 1.366(2) . ?
O2 C22 1.4314(19) . ?
O3 C6 1.4201(19) . ?
O3 C23 1.430(2) . ?
O4 H4 0.8642 . ?
O4 C20 1.4244(19) . ?
N1 C9 1.489(2) . ?
N1 C16 1.469(2) . ?
N1 C17 1.469(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.401(2) . ?
C1 C11 1.397(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.400(2) . ?
C3 C4 1.397(2) . ?
C4 C12 1.369(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.550(2) . ?
C5 C13 1.535(2) . ?
C6 C7 1.569(2) . ?
C6 C18 1.506(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.562(2) . ?
C7 C20 1.562(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.545(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.567(2) . ?
C9 C14 1.546(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.515(2) . ?
C11 C12 1.386(2) . ?
C12 C13 1.497(2) . ?
C13 C14 1.548(2) . ?
C13 C15 1.536(2) . ?
C14 C19 1.515(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.520(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 0.9500 . ?
C18 C19 1.332(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.535(2) . ?
C20 C24 1.520(2) . ?
C21 H21 1.0000 . ?
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 . ?
O1S H1S 0.9600 . ?
O1S C1S 1.410(3) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 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 106.78(12) . . ?
C3 O2 C22 116.09(14) . . ?
C6 O3 C23 117.44(13) . . ?
C20 O4 H4 110.1 . . ?
C16 N1 C9 111.73(12) . . ?
C16 N1 C17 109.46(13) . . ?
C17 N1 C9 112.52(13) . . ?
C2 C1 H1 119.4 . . ?
C11 C1 H1 119.4 . . ?
C11 C1 C2 121.18(15) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.40(14) . . ?
C3 C2 H2 119.3 . . ?
O2 C3 C2 125.81(14) . . ?
O2 C3 C4 117.63(14) . . ?
C4 C3 C2 116.50(15) . . ?
O1 C4 C3 125.88(15) . . ?
C12 C4 O1 112.87(13) . . ?
C12 C4 C3 120.93(15) . . ?
O1 C5 H5 108.9 . . ?
O1 C5 C6 114.26(12) . . ?
O1 C5 C13 106.95(11) . . ?
C6 C5 H5 108.9 . . ?
C13 C5 H5 108.9 . . ?
C13 C5 C6 108.86(13) . . ?
O3 C6 C5 111.69(13) . . ?
O3 C6 C7 107.24(12) . . ?
O3 C6 C18 115.34(13) . . ?
C5 C6 C7 103.59(12) . . ?
C18 C6 C5 109.70(12) . . ?
C18 C6 C7 108.53(13) . . ?
C6 C7 H7 106.4 . . ?
C8 C7 C6 109.48(12) . . ?
C8 C7 H7 106.4 . . ?
C8 C7 C20 109.95(13) . . ?
C20 C7 C6 117.47(13) . . ?
C20 C7 H7 106.4 . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C14 C8 C7 109.49(12) . . ?
C14 C8 H8A 109.8 . . ?
C14 C8 H8B 109.8 . . ?
N1 C9 H9 107.5 . . ?
N1 C9 C10 113.60(13) . . ?
N1 C9 C14 109.07(12) . . ?
C10 C9 H9 107.5 . . ?
C14 C9 H9 107.5 . . ?
C14 C9 C10 111.41(12) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 114.88(13) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C1 C11 C10 124.49(14) . . ?
C12 C11 C1 115.91(15) . . ?
C12 C11 C10 118.82(13) . . ?
C4 C12 C11 123.18(14) . . ?
C4 C12 C13 109.64(14) . . ?
C11 C12 C13 125.18(14) . . ?
C5 C13 C14 111.67(12) . . ?
C5 C13 C15 112.68(13) . . ?
C12 C13 C5 101.49(12) . . ?
C12 C13 C14 105.01(12) . . ?
C12 C13 C15 113.91(13) . . ?
C15 C13 C14 111.46(12) . . ?
C8 C14 C9 116.80(12) . . ?
C8 C14 C13 108.32(12) . . ?
C9 C14 C13 105.96(12) . . ?
C19 C14 C8 104.91(12) . . ?
C19 C14 C9 112.90(13) . . ?
C19 C14 C13 107.59(12) . . ?
C13 C15 H15A 109.3 . . ?
C13 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C13 111.66(13) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
N1 C16 C15 111.04(13) . . ?
N1 C16 H16A 109.4 . . ?
N1 C16 H16B 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C18 H18 122.6 . . ?
C19 C18 C6 114.74(14) . . ?
C19 C18 H18 122.6 . . ?
C14 C19 H19 122.4 . . ?
C18 C19 C14 115.27(14) . . ?
C18 C19 H19 122.4 . . ?
O4 C20 C7 107.53(13) . . ?
O4 C20 C21 107.61(13) . . ?
O4 C20 C24 106.84(14) . . ?
C21 C20 C7 112.35(13) . . ?
C24 C20 C7 114.87(13) . . ?
C24 C20 C21 107.30(15) . . ?
F1 C21 C20 109.54(15) . . ?
F1 C21 H21 110.4 . . ?
F2 C21 F1 105.24(15) . . ?
F2 C21 C20 110.63(15) . . ?
F2 C21 H21 110.4 . . ?
C20 C21 H21 110.4 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1S O1S H1S 103.8 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 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 162.71(15) . . . . ?
O1 C4 C12 C13 -1.91(19) . . . . ?
O1 C5 C6 O3 -61.77(16) . . . . ?
O1 C5 C6 C7 -176.88(12) . . . . ?
O1 C5 C6 C18 67.41(17) . . . . ?
O1 C5 C13 C12 -14.59(16) . . . . ?
O1 C5 C13 C14 -126.01(13) . . . . ?
O1 C5 C13 C15 107.63(14) . . . . ?
O2 C3 C4 O1 8.7(2) . . . . ?
O2 C3 C4 C12 -178.28(15) . . . . ?
O3 C6 C7 C8 173.99(12) . . . . ?
O3 C6 C7 C20 47.71(18) . . . . ?
O3 C6 C18 C19 -176.41(13) . . . . ?
O4 C20 C21 F1 -54.86(19) . . . . ?
O4 C20 C21 F2 60.71(18) . . . . ?
N1 C9 C10 C11 -96.47(17) . . . . ?
N1 C9 C14 C8 -58.09(17) . . . . ?
N1 C9 C14 C13 62.63(14) . . . . ?
N1 C9 C14 C19 -179.85(12) . . . . ?
C1 C2 C3 O2 -174.06(16) . . . . ?
C1 C2 C3 C4 3.1(2) . . . . ?
C1 C11 C12 C4 9.6(2) . . . . ?
C1 C11 C12 C13 171.83(15) . . . . ?
C2 C1 C11 C10 167.76(16) . . . . ?
C2 C1 C11 C12 -1.9(2) . . . . ?
C2 C3 C4 O1 -168.70(15) . . . . ?
C2 C3 C4 C12 4.3(2) . . . . ?
C3 C4 C12 C11 -11.1(3) . . . . ?
C3 C4 C12 C13 -175.76(15) . . . . ?
C4 O1 C5 C6 -106.31(14) . . . . ?
C4 O1 C5 C13 14.23(16) . . . . ?
C4 C12 C13 C5 10.25(17) . . . . ?
C4 C12 C13 C14 126.65(14) . . . . ?
C4 C12 C13 C15 -111.12(16) . . . . ?
C5 O1 C4 C3 165.54(16) . . . . ?
C5 O1 C4 C12 -7.95(18) . . . . ?
C5 C6 C7 C8 -67.78(15) . . . . ?
C5 C6 C7 C20 165.94(13) . . . . ?
C5 C6 C18 C19 56.44(18) . . . . ?
C5 C13 C14 C8 -58.73(15) . . . . ?
C5 C13 C14 C9 175.21(12) . . . . ?
C5 C13 C14 C19 54.19(15) . . . . ?
C5 C13 C15 C16 179.79(12) . . . . ?
C6 C5 C13 C12 109.33(13) . . . . ?
C6 C5 C13 C14 -2.09(16) . . . . ?
C6 C5 C13 C15 -128.44(13) . . . . ?
C6 C7 C8 C14 8.15(17) . . . . ?
C6 C7 C20 O4 176.93(13) . . . . ?
C6 C7 C20 C21 -64.85(18) . . . . ?
C6 C7 C20 C24 58.17(19) . . . . ?
C6 C18 C19 C14 -0.3(2) . . . . ?
C7 C6 C18 C19 -56.10(17) . . . . ?
C7 C8 C14 C9 173.44(13) . . . . ?
C7 C8 C14 C13 53.98(16) . . . . ?
C7 C8 C14 C19 -60.71(15) . . . . ?
C7 C20 C21 F1 -173.02(14) . . . . ?
C7 C20 C21 F2 -57.46(18) . . . . ?
C8 C7 C20 O4 50.88(16) . . . . ?
C8 C7 C20 C21 169.10(14) . . . . ?
C8 C7 C20 C24 -67.88(18) . . . . ?
C8 C14 C19 C18 59.90(17) . . . . ?
C9 N1 C16 C15 57.79(17) . . . . ?
C9 C10 C11 C1 -164.84(15) . . . . ?
C9 C10 C11 C12 4.6(2) . . . . ?
C9 C14 C19 C18 -171.86(14) . . . . ?
C10 C9 C14 C8 175.71(13) . . . . ?
C10 C9 C14 C13 -63.57(15) . . . . ?
C10 C9 C14 C19 53.95(17) . . . . ?
C10 C11 C12 C4 -160.68(16) . . . . ?
C10 C11 C12 C13 1.5(2) . . . . ?
C11 C1 C2 C3 -4.3(3) . . . . ?
C11 C12 C13 C5 -154.00(15) . . . . ?
C11 C12 C13 C14 -37.6(2) . . . . ?
C11 C12 C13 C15 84.64(19) . . . . ?
C12 C13 C14 C8 -167.91(13) . . . . ?
C12 C13 C14 C9 66.03(14) . . . . ?
C12 C13 C14 C19 -54.99(15) . . . . ?
C12 C13 C15 C16 -65.28(18) . . . . ?
C13 C5 C6 O3 178.76(12) . . . . ?
C13 C5 C6 C7 63.65(14) . . . . ?
C13 C5 C6 C18 -52.07(16) . . . . ?
C13 C14 C19 C18 -55.29(17) . . . . ?
C13 C15 C16 N1 -51.51(17) . . . . ?
C14 C9 C10 C11 27.20(19) . . . . ?
C14 C13 C15 C16 53.32(17) . . . . ?
C15 C13 C14 C8 68.29(15) . . . . ?
C15 C13 C14 C9 -57.78(15) . . . . ?
C15 C13 C14 C19 -178.80(12) . . . . ?
C16 N1 C9 C10 60.24(17) . . . . ?
C16 N1 C9 C14 -64.69(15) . . . . ?
C17 N1 C9 C10 -63.37(17) . . . . ?
C17 N1 C9 C14 171.70(13) . . . . ?
C17 N1 C16 C15 -176.90(13) . . . . ?
C18 C6 C7 C8 48.77(16) . . . . ?
C18 C6 C7 C20 -77.52(16) . . . . ?
C20 C7 C8 C14 138.61(13) . . . . ?
C22 O2 C3 C2 -1.5(2) . . . . ?
C22 O2 C3 C4 -178.63(15) . . . . ?
C23 O3 C6 C5 70.78(17) . . . . ?
C23 O3 C6 C7 -176.38(14) . . . . ?
C23 O3 C6 C18 -55.37(19) . . . . ?
C24 C20 C21 F1 59.80(18) . . . . ?
C24 C20 C21 F2 175.37(15) . . . . ?

_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_41c
_database_code_depnum_ccdc_archive 'CCDC 2291937'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-09-12 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H37 F2 N O4, H2 O'
_chemical_formula_sum            'C27 H39 F2 N O5'
_chemical_formula_weight         495.59
_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      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                   9.3792(2)
_cell_length_b                   12.5351(2)
_cell_length_c                   20.4300(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2401.94(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1109 before and 0.0545 after correction.
The Ratio of minimum to maximum transmission is 0.9121.
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    1.370
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            32636
_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         28.997
_diffrn_reflns_theta_min         1.906
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5902
_reflns_number_total             6392
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2402 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         6392
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+0.3545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1007
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C24'-C23' \\sim C24-C23
 with sigma of 0.02
 C23'-C22 \\sim C23-C22
 with sigma of 0.02
 C25'-C24' \\sim C25-C24
 with sigma of 0.02
 C25-C24 \\sim C25'-C24'
 with sigma of 0.02
 C24-C23 \\sim C24'-C23'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C23) = Uanis(C23')
Uanis(C24') = Uanis(C24)
Uanis(C24) = Uanis(C24')
Uanis(C25') = Uanis(C25)
4. Others
 Sof(C23')=Sof(H23C)=Sof(H23D)=Sof(C24')=Sof(H24C)=Sof(H24D)=Sof(C25')=
 Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=
 Sof(H25B)=Sof(H25C)=FVAR(1)
5.a Riding coordinates:
 O4(H4), C22(H22A,H22B), O1S(H1SA,H1SB)
5.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C21(H21)
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B),
 C19(H19A,H19B), C23(H23A,H23B), C24(H24A,H24B), C23'(H23C,H23D), C24'(H24C,
 H24D)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
5.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C25(H25A,H25B,
 H25C), C25'(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
F1 F 0.60281(14) 0.14510(11) 0.34382(6) 0.0262(3) Uani 1 1 d . . . . .
F2 F 0.60021(14) 0.08155(10) 0.44329(6) 0.0268(3) Uani 1 1 d . . . . .
O1 O 0.62005(15) 0.57701(11) 0.30499(7) 0.0188(3) Uani 1 1 d . . . . .
O2 O 0.78170(16) 0.77020(13) 0.30204(8) 0.0268(3) Uani 1 1 d . . . . .
O3 O 0.68932(15) 0.36461(12) 0.35157(7) 0.0191(3) Uani 1 1 d . . . . .
O4 O 0.47929(16) 0.26945(12) 0.49066(7) 0.0211(3) Uani 1 1 d . . . . .
H4 H 0.4713 0.2149 0.5144 0.025 Uiso 1 1 d R U . . .
N1 N 0.09022(18) 0.57659(15) 0.39374(9) 0.0224(4) Uani 1 1 d . . . . .
C1 C 0.4587(3) 0.84074(18) 0.39935(12) 0.0283(5) Uani 1 1 d . . . . .
H1 H 0.4217 0.8989 0.4239 0.034 Uiso 1 1 calc R U . . .
C2 C 0.5885(3) 0.85228(18) 0.36594(12) 0.0278(5) Uani 1 1 d . . . . .
H2 H 0.6357 0.9193 0.3668 0.033 Uiso 1 1 calc R U . . .
C3 C 0.6501(2) 0.76818(17) 0.33149(10) 0.0221(4) Uani 1 1 d . . . . .
C4 C 0.5728(2) 0.67340(16) 0.32877(10) 0.0187(4) Uani 1 1 d . . . . .
C5 C 0.5097(2) 0.49720(16) 0.32103(9) 0.0166(4) Uani 1 1 d . . . . .
H5 H 0.4810 0.4586 0.2803 0.020 Uiso 1 1 calc R U . . .
C6 C 0.5605(2) 0.41635(16) 0.37226(9) 0.0158(4) Uani 1 1 d . . . . .
C7 C 0.4336(2) 0.33733(15) 0.38205(9) 0.0150(3) Uani 1 1 d . . . . .
H7 H 0.4049 0.3120 0.3375 0.018 Uiso 1 1 calc R U . . .
C8 C 0.3019(2) 0.39909(15) 0.41128(9) 0.0163(4) Uani 1 1 d . . . . .
H8A H 0.2178 0.3889 0.3827 0.020 Uiso 1 1 calc R U . . .
H8B H 0.2787 0.3704 0.4552 0.020 Uiso 1 1 calc R U . . .
C9 C 0.2130(2) 0.59323(16) 0.43789(10) 0.0191(4) Uani 1 1 d . . . . .
H9 H 0.1829 0.5709 0.4828 0.023 Uiso 1 1 calc R U . . .
C10 C 0.2612(2) 0.71336(17) 0.44190(11) 0.0245(4) Uani 1 1 d . . . . .
H10A H 0.1780 0.7590 0.4316 0.029 Uiso 1 1 calc R U . . .
H10B H 0.2897 0.7289 0.4876 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3833(2) 0.74502(17) 0.39692(11) 0.0230(4) Uani 1 1 d . . . . .
C12 C 0.4397(2) 0.66784(16) 0.35640(10) 0.0187(4) Uani 1 1 d . . . . .
C13 C 0.3806(2) 0.55824(15) 0.34840(9) 0.0164(4) Uani 1 1 d . . . . .
C14 C 0.3368(2) 0.51870(15) 0.41655(9) 0.0152(4) Uani 1 1 d . . . . .
C15 C 0.2534(2) 0.55395(17) 0.30086(10) 0.0204(4) Uani 1 1 d . . . . .
H15A H 0.2819 0.5862 0.2586 0.025 Uiso 1 1 calc R U . . .
H15B H 0.2282 0.4785 0.2926 0.025 Uiso 1 1 calc R U . . .
C16 C 0.1231(2) 0.61205(19) 0.32686(11) 0.0253(4) Uani 1 1 d . . . . .
H16A H 0.1411 0.6899 0.3268 0.030 Uiso 1 1 calc R U . . .
H16B H 0.0404 0.5978 0.2980 0.030 Uiso 1 1 calc R U . . .
C17 C -0.0406(2) 0.6276(2) 0.41776(12) 0.0303(5) Uani 1 1 d . . . . .
H17A H -0.0662 0.5973 0.4604 0.045 Uiso 1 1 calc R U . . .
H17B H -0.1182 0.6150 0.3866 0.045 Uiso 1 1 calc R U . . .
H17C H -0.0247 0.7045 0.4223 0.045 Uiso 1 1 calc R U . . .
C18 C 0.5971(2) 0.47431(16) 0.43592(9) 0.0174(4) Uani 1 1 d . . . . .
H18A H 0.6697 0.5298 0.4272 0.021 Uiso 1 1 calc R U . . .
H18B H 0.6377 0.4230 0.4677 0.021 Uiso 1 1 calc R U . . .
C19 C 0.4622(2) 0.52655(17) 0.46528(9) 0.0178(4) Uani 1 1 d . . . . .
H19A H 0.4365 0.4902 0.5066 0.021 Uiso 1 1 calc R U . . .
H19B H 0.4818 0.6024 0.4753 0.021 Uiso 1 1 calc R U . . .
C20 C 0.4596(2) 0.23559(16) 0.42474(9) 0.0178(4) Uani 1 1 d . . . . .
C21 C 0.5966(2) 0.17576(17) 0.40816(10) 0.0214(4) Uani 1 1 d . . . . .
H21 H 0.6814 0.2206 0.4193 0.026 Uiso 1 1 calc R U . . .
C22 C 0.3283(2) 0.16075(16) 0.42058(10) 0.0195(4) Uani 1 1 d D . . . .
H22A H 0.3438 0.1019 0.4521 0.023 Uiso 1 1 d R U . A .
H22B H 0.2438 0.2027 0.4340 0.023 Uiso 1 1 d R U . . .
C26 C 0.8728(3) 0.8567(2) 0.31898(13) 0.0328(5) Uani 1 1 d . . . . .
H26A H 0.9653 0.8475 0.2974 0.049 Uiso 1 1 calc R U . . .
H26B H 0.8864 0.8581 0.3665 0.049 Uiso 1 1 calc R U . . .
H26C H 0.8295 0.9239 0.3047 0.049 Uiso 1 1 calc R U . . .
C27 C 0.7035(2) 0.33967(19) 0.28316(11) 0.0252(4) Uani 1 1 d . . . . .
H27A H 0.6194 0.2999 0.2685 0.038 Uiso 1 1 calc R U . . .
H27B H 0.7890 0.2962 0.2764 0.038 Uiso 1 1 calc R U . . .
H27C H 0.7116 0.4059 0.2580 0.038 Uiso 1 1 calc R U . . .
C23 C 0.2946(3) 0.1101(2) 0.35398(12) 0.0244(5) Uani 0.956(5) 1 d D . P A 1
H23A H 0.3709 0.0588 0.3425 0.029 Uiso 0.956(5) 1 calc R U P A 1
H23B H 0.2931 0.1664 0.3200 0.029 Uiso 0.956(5) 1 calc R U P A 1
C24 C 0.1504(3) 0.0520(2) 0.35443(15) 0.0308(6) Uani 0.956(5) 1 d D . P A 1
H24A H 0.1449 0.0053 0.3154 0.037 Uiso 0.956(5) 1 calc R U P A 1
H24B H 0.1458 0.0057 0.3936 0.037 Uiso 0.956(5) 1 calc R U P A 1
C25 C 0.0224(3) 0.1255(2) 0.35461(15) 0.0362(6) Uani 0.956(5) 1 d D . P A 1
H25A H 0.0259 0.1719 0.3160 0.054 Uiso 0.956(5) 1 calc R U P A 1
H25B H 0.0237 0.1693 0.3943 0.054 Uiso 0.956(5) 1 calc R U P A 1
H25C H -0.0652 0.0829 0.3536 0.054 Uiso 0.956(5) 1 calc R U P A 1
C23' C 0.255(5) 0.094(5) 0.364(2) 0.0244(5) Uani 0.044(5) 1 d D . P A 2
H23C H 0.2762 0.1296 0.3218 0.029 Uiso 0.044(5) 1 calc R U P A 2
H23D H 0.2996 0.0226 0.3628 0.029 Uiso 0.044(5) 1 calc R U P A 2
C24' C 0.093(5) 0.080(5) 0.369(2) 0.0308(6) Uani 0.044(5) 1 d D . P A 2
H24C H 0.0705 0.0086 0.3876 0.037 Uiso 0.044(5) 1 calc R U P A 2
H24D H 0.0520 0.1349 0.3983 0.037 Uiso 0.044(5) 1 calc R U P A 2
C25' C 0.033(6) 0.090(5) 0.301(2) 0.0362(6) Uani 0.044(5) 1 d D . P A 2
H25D H -0.0608 0.0566 0.2994 0.054 Uiso 0.044(5) 1 calc R U P A 2
H25E H 0.0974 0.0549 0.2700 0.054 Uiso 0.044(5) 1 calc R U P A 2
H25F H 0.0249 0.1659 0.2898 0.054 Uiso 0.044(5) 1 calc R U P A 2
O1S O 0.45096(17) 0.12356(13) 0.58705(8) 0.0280(3) Uani 1 1 d . . . . .
H1SA H 0.3718 0.1155 0.6121 0.034 Uiso 1 1 d R U . . .
H1SB H 0.4990 0.0596 0.5967 0.034 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
F1 C21 1.371(2) . ?
F2 C21 1.382(2) . ?
O1 C4 1.376(3) . ?
O1 C5 1.477(2) . ?
O2 C3 1.374(3) . ?
O2 C26 1.423(3) . ?
O3 C6 1.435(2) . ?
O3 C27 1.438(3) . ?
O4 H4 0.8419 . ?
O4 C20 1.424(2) . ?
N1 C9 1.478(3) . ?
N1 C16 1.469(3) . ?
N1 C17 1.468(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.403(3) . ?
C1 C11 1.393(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C3 C4 1.393(3) . ?
C4 C12 1.372(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.533(3) . ?
C5 C13 1.537(3) . ?
C6 C7 1.561(3) . ?
C6 C18 1.529(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.575(3) . ?
C7 C20 1.564(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.538(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.574(3) . ?
C9 C14 1.553(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.521(3) . ?
C11 C12 1.379(3) . ?
C12 C13 1.490(3) . ?
C13 C14 1.534(3) . ?
C13 C15 1.540(3) . ?
C14 C19 1.544(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.519(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.546(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.526(3) . ?
C20 C22 1.550(3) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.535(3) . ?
C22 C23' 1.58(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.536(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.513(4) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C23' H23C 0.9900 . ?
C23' H23D 0.9900 . ?
C23' C24' 1.53(3) . ?
C24' H24C 0.9900 . ?
C24' H24D 0.9900 . ?
C24' C25' 1.51(3) . ?
C25' H25D 0.9800 . ?
C25' H25E 0.9800 . ?
C25' H25F 0.9800 . ?
O1S H1SA 0.9071 . ?
O1S H1SB 0.9408 . ?

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 106.90(15) . . ?
C3 O2 C26 116.57(19) . . ?
C6 O3 C27 117.52(15) . . ?
C20 O4 H4 106.9 . . ?
C16 N1 C9 111.20(16) . . ?
C17 N1 C9 112.68(18) . . ?
C17 N1 C16 110.76(17) . . ?
C2 C1 H1 119.6 . . ?
C11 C1 H1 119.6 . . ?
C11 C1 C2 120.8(2) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.8(2) . . ?
C3 C2 H2 119.1 . . ?
O2 C3 C2 125.5(2) . . ?
O2 C3 C4 117.8(2) . . ?
C4 C3 C2 116.74(19) . . ?
O1 C4 C3 126.57(18) . . ?
C12 C4 O1 113.20(18) . . ?
C12 C4 C3 120.0(2) . . ?
O1 C5 H5 109.4 . . ?
O1 C5 C6 112.43(15) . . ?
O1 C5 C13 107.20(15) . . ?
C6 C5 H5 109.4 . . ?
C6 C5 C13 109.00(15) . . ?
C13 C5 H5 109.4 . . ?
O3 C6 C5 111.06(15) . . ?
O3 C6 C7 113.14(15) . . ?
O3 C6 C18 106.01(15) . . ?
C5 C6 C7 105.67(15) . . ?
C18 C6 C5 109.67(16) . . ?
C18 C6 C7 111.34(15) . . ?
C6 C7 H7 106.9 . . ?
C6 C7 C8 109.53(15) . . ?
C6 C7 C20 118.03(16) . . ?
C8 C7 H7 106.9 . . ?
C20 C7 H7 106.9 . . ?
C20 C7 C8 108.16(15) . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C14 C8 C7 109.81(15) . . ?
C14 C8 H8A 109.7 . . ?
C14 C8 H8B 109.7 . . ?
N1 C9 H9 107.5 . . ?
N1 C9 C10 113.00(17) . . ?
N1 C9 C14 109.06(16) . . ?
C10 C9 H9 107.5 . . ?
C14 C9 H9 107.5 . . ?
C14 C9 C10 112.03(16) . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 115.75(17) . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C1 C11 C10 125.8(2) . . ?
C12 C11 C1 115.5(2) . . ?
C12 C11 C10 117.93(19) . . ?
C4 C12 C11 124.1(2) . . ?
C4 C12 C13 109.88(18) . . ?
C11 C12 C13 124.76(19) . . ?
C5 C13 C15 111.32(16) . . ?
C12 C13 C5 101.88(15) . . ?
C12 C13 C14 107.32(16) . . ?
C12 C13 C15 112.94(16) . . ?
C14 C13 C5 112.34(15) . . ?
C14 C13 C15 110.72(15) . . ?
C8 C14 C9 116.54(16) . . ?
C8 C14 C19 105.62(15) . . ?
C13 C14 C8 107.95(15) . . ?
C13 C14 C9 105.11(15) . . ?
C13 C14 C19 111.15(16) . . ?
C19 C14 C9 110.51(16) . . ?
C13 C15 H15A 109.0 . . ?
C13 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C13 112.73(17) . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
N1 C16 C15 110.42(17) . . ?
N1 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C18 H18A 109.6 . . ?
C6 C18 H18B 109.6 . . ?
C6 C18 C19 110.31(15) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
C14 C19 C18 110.26(15) . . ?
C14 C19 H19A 109.6 . . ?
C14 C19 H19B 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
O4 C20 C7 107.73(15) . . ?
O4 C20 C21 104.29(16) . . ?
O4 C20 C22 109.59(15) . . ?
C21 C20 C7 114.09(16) . . ?
C21 C20 C22 111.05(16) . . ?
C22 C20 C7 109.82(16) . . ?
F1 C21 F2 104.91(16) . . ?
F1 C21 C20 112.73(16) . . ?
F1 C21 H21 110.0 . . ?
F2 C21 C20 108.97(17) . . ?
F2 C21 H21 110.0 . . ?
C20 C21 H21 110.0 . . ?
C20 C22 H22A 107.4 . . ?
C20 C22 H22B 107.4 . . ?
C20 C22 C23' 135(2) . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 C20 117.57(17) . . ?
C23 C22 H22A 107.4 . . ?
C23 C22 H22B 107.5 . . ?
C23' C22 H22A 98.4 . . ?
C23' C22 H22B 97.7 . . ?
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 . . ?
C22 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
C22 C23 C24 111.9(2) . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 H23A 109.2 . . ?
C24 C23 H23B 109.2 . . ?
C23 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 C23 114.2(2) . . ?
C25 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
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 . . ?
C22 C23' H23C 108.2 . . ?
C22 C23' H23D 108.2 . . ?
H23C C23' H23D 107.4 . . ?
C24' C23' C22 116(3) . . ?
C24' C23' H23C 108.2 . . ?
C24' C23' H23D 108.2 . . ?
C23' C24' H24C 110.3 . . ?
C23' C24' H24D 110.3 . . ?
H24C C24' H24D 108.6 . . ?
C25' C24' C23' 107(4) . . ?
C25' C24' H24C 110.3 . . ?
C25' C24' H24D 110.3 . . ?
C24' C25' H25D 109.5 . . ?
C24' C25' H25E 109.5 . . ?
C24' C25' H25F 109.5 . . ?
H25D C25' H25E 109.5 . . ?
H25D C25' H25F 109.5 . . ?
H25E C25' H25F 109.5 . . ?
H1SA O1S H1SB 100.3 . . ?

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
O1 C4 C12 C11 163.86(19) . . . . ?
O1 C4 C12 C13 -3.7(2) . . . . ?
O1 C5 C6 O3 -55.6(2) . . . . ?
O1 C5 C6 C7 -178.69(15) . . . . ?
O1 C5 C6 C18 61.2(2) . . . . ?
O1 C5 C13 C12 -9.59(18) . . . . ?
O1 C5 C13 C14 -124.13(16) . . . . ?
O1 C5 C13 C15 111.05(17) . . . . ?
O2 C3 C4 O1 6.9(3) . . . . ?
O2 C3 C4 C12 -178.82(18) . . . . ?
O3 C6 C7 C8 174.44(14) . . . . ?
O3 C6 C7 C20 50.1(2) . . . . ?
O3 C6 C18 C19 -175.98(15) . . . . ?
O4 C20 C21 F1 -174.39(15) . . . . ?
O4 C20 C21 F2 69.57(19) . . . . ?
O4 C20 C22 C23 -176.35(18) . . . . ?
O4 C20 C22 C23' -177(4) . . . . ?
N1 C9 C10 C11 -95.9(2) . . . . ?
N1 C9 C14 C8 -54.4(2) . . . . ?
N1 C9 C14 C13 65.04(19) . . . . ?
N1 C9 C14 C19 -174.96(16) . . . . ?
C1 C2 C3 O2 -174.4(2) . . . . ?
C1 C2 C3 C4 3.4(3) . . . . ?
C1 C11 C12 C4 11.5(3) . . . . ?
C1 C11 C12 C13 177.30(19) . . . . ?
C2 C1 C11 C10 165.5(2) . . . . ?
C2 C1 C11 C12 -4.5(3) . . . . ?
C2 C3 C4 O1 -171.15(19) . . . . ?
C2 C3 C4 C12 3.2(3) . . . . ?
C3 C4 C12 C11 -11.2(3) . . . . ?
C3 C4 C12 C13 -178.79(18) . . . . ?
C4 O1 C5 C6 -111.82(18) . . . . ?
C4 O1 C5 C13 7.95(19) . . . . ?
C4 C12 C13 C5 8.2(2) . . . . ?
C4 C12 C13 C14 126.36(17) . . . . ?
C4 C12 C13 C15 -111.34(19) . . . . ?
C5 O1 C4 C3 171.85(19) . . . . ?
C5 O1 C4 C12 -2.8(2) . . . . ?
C5 C6 C7 C8 -63.84(18) . . . . ?
C5 C6 C7 C20 171.87(16) . . . . ?
C5 C6 C18 C19 64.0(2) . . . . ?
C5 C13 C14 C8 -58.46(19) . . . . ?
C5 C13 C14 C9 176.50(15) . . . . ?
C5 C13 C14 C19 56.9(2) . . . . ?
C5 C13 C15 C16 179.09(16) . . . . ?
C6 C5 C13 C12 112.36(17) . . . . ?
C6 C5 C13 C14 -2.2(2) . . . . ?
C6 C5 C13 C15 -127.00(17) . . . . ?
C6 C7 C8 C14 3.8(2) . . . . ?
C6 C7 C20 O4 68.4(2) . . . . ?
C6 C7 C20 C21 -46.9(2) . . . . ?
C6 C7 C20 C22 -172.33(16) . . . . ?
C6 C18 C19 C14 -8.4(2) . . . . ?
C7 C6 C18 C19 -52.5(2) . . . . ?
C7 C8 C14 C9 173.97(15) . . . . ?
C7 C8 C14 C13 56.06(19) . . . . ?
C7 C8 C14 C19 -62.91(19) . . . . ?
C7 C20 C21 F1 -57.1(2) . . . . ?
C7 C20 C21 F2 -173.16(16) . . . . ?
C7 C20 C22 C23 65.5(2) . . . . ?
C7 C20 C22 C23' 65(4) . . . . ?
C8 C7 C20 O4 -56.60(19) . . . . ?
C8 C7 C20 C21 -171.88(16) . . . . ?
C8 C7 C20 C22 62.71(19) . . . . ?
C8 C14 C19 C18 66.57(19) . . . . ?
C9 N1 C16 C15 57.3(2) . . . . ?
C9 C10 C11 C1 -169.0(2) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C9 C14 C19 C18 -166.56(16) . . . . ?
C10 C9 C14 C8 179.73(17) . . . . ?
C10 C9 C14 C13 -60.8(2) . . . . ?
C10 C9 C14 C19 59.2(2) . . . . ?
C10 C11 C12 C4 -159.3(2) . . . . ?
C10 C11 C12 C13 6.5(3) . . . . ?
C11 C1 C2 C3 -2.7(4) . . . . ?
C11 C12 C13 C5 -159.3(2) . . . . ?
C11 C12 C13 C14 -41.1(3) . . . . ?
C11 C12 C13 C15 81.2(3) . . . . ?
C12 C13 C14 C8 -169.64(15) . . . . ?
C12 C13 C14 C9 65.33(18) . . . . ?
C12 C13 C14 C19 -54.2(2) . . . . ?
C12 C13 C15 C16 -67.0(2) . . . . ?
C13 C5 C6 O3 -174.35(15) . . . . ?
C13 C5 C6 C7 62.60(19) . . . . ?
C13 C5 C6 C18 -57.51(19) . . . . ?
C13 C14 C19 C18 -50.3(2) . . . . ?
C13 C15 C16 N1 -50.6(2) . . . . ?
C14 C9 C10 C11 27.8(3) . . . . ?
C14 C13 C15 C16 53.4(2) . . . . ?
C15 C13 C14 C8 66.7(2) . . . . ?
C15 C13 C14 C9 -58.35(19) . . . . ?
C15 C13 C14 C19 -177.92(16) . . . . ?
C16 N1 C9 C10 59.0(2) . . . . ?
C16 N1 C9 C14 -66.3(2) . . . . ?
C17 N1 C9 C10 -66.1(2) . . . . ?
C17 N1 C9 C14 168.64(16) . . . . ?
C17 N1 C16 C15 -176.59(18) . . . . ?
C18 C6 C7 C8 55.2(2) . . . . ?
C18 C6 C7 C20 -69.1(2) . . . . ?
C20 C7 C8 C14 133.63(16) . . . . ?
C20 C22 C23 C24 -171.4(2) . . . . ?
C20 C22 C23' C24' -149(4) . . . . ?
C21 C20 C22 C23 -61.6(2) . . . . ?
C21 C20 C22 C23' -62(4) . . . . ?
C22 C20 C21 F1 67.7(2) . . . . ?
C22 C20 C21 F2 -48.4(2) . . . . ?
C22 C23 C24 C25 73.3(3) . . . . ?
C22 C23' C24' C25' 140(5) . . . . ?
C26 O2 C3 C2 13.0(3) . . . . ?
C26 O2 C3 C4 -164.76(19) . . . . ?
C27 O3 C6 C5 -37.4(2) . . . . ?
C27 O3 C6 C7 81.2(2) . . . . ?
C27 O3 C6 C18 -156.49(17) . . . . ?

_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 2296708'
loop_
_audit_author_name
_audit_author_address
"Alexander Smol'yakov"
;Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-09-22 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 F3 N O4'
_chemical_formula_sum            'C23 H24 F3 N O4'
_chemical_formula_weight         435.43
_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                   9.1217(3)
_cell_length_b                   11.2737(3)
_cell_length_c                   19.5547(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2010.91(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6923
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.340
_cell_measurement_theta_min      2.464
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            20876
_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         25.999
_diffrn_reflns_theta_min         2.083
_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       ?
_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         0.746
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3476
_reflns_number_total             3938
_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         0.189
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1392 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   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3938
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0321
_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)+(0.0378P)²+0.2015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0742
_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), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C15(H15a,H15b), C16(H16a,H16b), C18(H18a,H18b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C19(H19)
2.d Idealised Me refined as rotating group:
 C17(H17a,H17b,H17c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c)
;
_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 0.67093(18) 0.84686(11) 0.45822(7) 0.0260(4) Uani 1 1 d . . . . .
F2 F 0.66105(17) 0.72763(12) 0.54389(7) 0.0249(3) Uani 1 1 d . . . . .
F3 F 0.46294(16) 0.79866(12) 0.50187(8) 0.0308(4) Uani 1 1 d . . . . .
O1 O 0.13454(19) 0.06224(14) 0.31703(8) 0.0185(4) Uani 1 1 d . . . . .
O2 O 0.27611(18) 0.27595(14) 0.27550(8) 0.0158(4) Uani 1 1 d . . . . .
O3 O 0.1516(2) 0.50551(13) 0.29271(8) 0.0178(4) Uani 1 1 d . . . . .
O4 O 0.51393(18) 0.56099(13) 0.46735(8) 0.0156(4) Uani 1 1 d . . . . .
N1 N 0.8133(2) 0.33661(18) 0.35060(10) 0.0179(5) Uani 1 1 d . . . . .
C1 C 0.4516(3) 0.0878(2) 0.43641(12) 0.0174(5) Uani 1 1 d . . . . .
H1 H 0.491818 0.048133 0.474946 0.021 Uiso 1 1 calc R U . . .
C2 C 0.3259(3) 0.0422(2) 0.40556(12) 0.0181(5) Uani 1 1 d . . . . .
H2 H 0.284718 -0.029253 0.422647 0.022 Uiso 1 1 calc R U . . .
C3 C 0.2588(3) 0.0988(2) 0.35016(12) 0.0158(5) Uani 1 1 d . . . . .
C4 C 0.3257(3) 0.2020(2) 0.32687(11) 0.0145(5) Uani 1 1 d . . . . .
C5 C 0.3621(3) 0.38652(19) 0.28290(12) 0.0159(5) Uani 1 1 d . . . . .
H5 H 0.382265 0.421196 0.236783 0.019 Uiso 1 1 calc R U . . .
C6 C 0.2773(3) 0.47383(19) 0.32553(12) 0.0149(5) Uani 1 1 d . . . . .
C7 C 0.3212(3) 0.51393(19) 0.38631(12) 0.0151(5) Uani 1 1 d . . . . .
H7 H 0.262879 0.571365 0.409186 0.018 Uiso 1 1 calc R U . . .
C8 C 0.4599(3) 0.47144(19) 0.41994(11) 0.0149(5) Uani 1 1 d . . . . .
H8 H 0.434578 0.399487 0.447411 0.018 Uiso 1 1 calc R U . . .
C9 C 0.7035(3) 0.3647(2) 0.40318(12) 0.0161(5) Uani 1 1 d . . . . .
H9 H 0.750928 0.419629 0.436711 0.019 Uiso 1 1 calc R U . . .
C10 C 0.6478(3) 0.25422(19) 0.44407(11) 0.0167(5) Uani 1 1 d . . . . .
H10A H 0.730002 0.197546 0.449065 0.020 Uiso 1 1 calc R U . . .
H10B H 0.619166 0.280331 0.490531 0.020 Uiso 1 1 calc R U . . .
C11 C 0.5200(3) 0.19023(19) 0.41221(12) 0.0147(5) Uani 1 1 d . . . . .
C12 C 0.4546(3) 0.24063(19) 0.35532(11) 0.0145(5) Uani 1 1 d . . . . .
C13 C 0.5069(3) 0.3479(2) 0.31657(11) 0.0148(5) Uani 1 1 d . . . . .
C14 C 0.5769(3) 0.4346(2) 0.36783(11) 0.0137(5) Uani 1 1 d . . . . .
C15 C 0.6221(3) 0.3100(2) 0.26309(12) 0.0185(6) Uani 1 1 d . . . . .
H15A H 0.578705 0.250230 0.232027 0.022 Uiso 1 1 calc R U . . .
H15B H 0.650708 0.379702 0.235311 0.022 Uiso 1 1 calc R U . . .
C16 C 0.7579(3) 0.2580(2) 0.29728(12) 0.0196(6) Uani 1 1 d . . . . .
H16A H 0.733203 0.180024 0.317543 0.024 Uiso 1 1 calc R U . . .
H16B H 0.835164 0.245342 0.262484 0.024 Uiso 1 1 calc R U . . .
C17 C 0.9508(3) 0.2921(2) 0.37845(13) 0.0223(6) Uani 1 1 d . . . . .
H17A H 0.935377 0.212683 0.397561 0.033 Uiso 1 1 calc R U . . .
H17B H 0.985286 0.345543 0.414547 0.033 Uiso 1 1 calc R U . . .
H17C H 1.024353 0.288013 0.341983 0.033 Uiso 1 1 calc R U . . .
C18 C 0.6342(3) 0.5457(2) 0.33022(12) 0.0162(5) Uani 1 1 d . . . . .
H18A H 0.732608 0.528354 0.311358 0.019 Uiso 1 1 calc R U . . .
H18B H 0.568232 0.563524 0.291355 0.019 Uiso 1 1 calc R U . . .
C19 C 0.6438(3) 0.6524(2) 0.37534(12) 0.0168(5) Uani 1 1 d . . . . .
H19 H 0.692671 0.721321 0.359109 0.020 Uiso 1 1 calc R U . . .
C20 C 0.5863(3) 0.6531(2) 0.43696(12) 0.0156(5) Uani 1 1 d . . . . .
C21 C 0.5956(3) 0.7562(2) 0.48468(12) 0.0191(5) Uani 1 1 d . . . . .
C22 C 0.0607(3) -0.0385(2) 0.34468(13) 0.0227(6) Uani 1 1 d . . . . .
H22A H -0.027771 -0.054668 0.317803 0.034 Uiso 1 1 calc R U . . .
H22B H 0.033272 -0.022482 0.392251 0.034 Uiso 1 1 calc R U . . .
H22C H 0.125815 -0.107582 0.342986 0.034 Uiso 1 1 calc R U . . .
C23 C 0.0553(3) 0.5843(2) 0.32849(13) 0.0196(5) Uani 1 1 d . . . . .
H23A H -0.027579 0.605061 0.298949 0.029 Uiso 1 1 calc R U . . .
H23B H 0.108737 0.656525 0.341066 0.029 Uiso 1 1 calc R U . . .
H23C H 0.018969 0.545319 0.369941 0.029 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 1.336(3) . ?
F2 C21 1.342(3) . ?
F3 C21 1.344(3) . ?
O1 C3 1.369(3) . ?
O1 C22 1.427(3) . ?
O2 C4 1.382(3) . ?
O2 C5 1.480(3) . ?
O3 C6 1.362(3) . ?
O3 C23 1.432(3) . ?
O4 C8 1.456(3) . ?
O4 C20 1.367(3) . ?
N1 C9 1.469(3) . ?
N1 C16 1.459(3) . ?
N1 C17 1.457(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.394(4) . ?
C1 C11 1.395(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.399(3) . ?
C3 C4 1.390(3) . ?
C4 C12 1.372(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.504(3) . ?
C5 C13 1.539(3) . ?
C6 C7 1.333(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.504(3) . ?
C8 H8 1.0000 . ?
C8 C14 1.532(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.565(3) . ?
C9 C14 1.560(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.506(3) . ?
C11 C12 1.384(3) . ?
C12 C13 1.504(3) . ?
C13 C14 1.539(3) . ?
C13 C15 1.543(3) . ?
C14 C18 1.543(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.525(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.495(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.314(3) . ?
C20 C21 1.493(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C3 O1 C22 116.84(18) . . ?
C4 O2 C5 105.29(16) . . ?
C6 O3 C23 116.67(17) . . ?
C20 O4 C8 114.41(16) . . ?
C16 N1 C9 113.29(19) . . ?
C17 N1 C9 113.53(19) . . ?
C17 N1 C16 110.84(19) . . ?
C2 C1 H1 119.1 . . ?
C2 C1 C11 121.7(2) . . ?
C11 C1 H1 119.1 . . ?
C1 C2 H2 119.1 . . ?
C1 C2 C3 121.8(2) . . ?
C3 C2 H2 119.1 . . ?
O1 C3 C2 126.3(2) . . ?
O1 C3 C4 117.4(2) . . ?
C4 C3 C2 116.3(2) . . ?
O2 C4 C3 126.8(2) . . ?
C12 C4 O2 112.57(19) . . ?
C12 C4 C3 120.6(2) . . ?
O2 C5 H5 109.8 . . ?
O2 C5 C6 109.44(19) . . ?
O2 C5 C13 104.98(17) . . ?
C6 C5 H5 109.8 . . ?
C6 C5 C13 112.92(19) . . ?
C13 C5 H5 109.8 . . ?
O3 C6 C5 110.09(19) . . ?
C7 C6 O3 125.8(2) . . ?
C7 C6 C5 124.2(2) . . ?
C6 C7 H7 118.8 . . ?
C6 C7 C8 122.3(2) . . ?
C8 C7 H7 118.8 . . ?
O4 C8 C7 109.99(18) . . ?
O4 C8 H8 107.4 . . ?
O4 C8 C14 112.07(19) . . ?
C7 C8 H8 107.4 . . ?
C7 C8 C14 112.40(18) . . ?
C14 C8 H8 107.4 . . ?
N1 C9 H9 107.3 . . ?
N1 C9 C10 114.03(19) . . ?
N1 C9 C14 107.66(18) . . ?
C10 C9 H9 107.3 . . ?
C14 C9 H9 107.3 . . ?
C14 C9 C10 112.81(19) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 114.92(19) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C1 C11 C10 127.0(2) . . ?
C12 C11 C1 114.8(2) . . ?
C12 C11 C10 118.0(2) . . ?
C4 C12 C11 124.4(2) . . ?
C4 C12 C13 108.8(2) . . ?
C11 C12 C13 126.8(2) . . ?
C5 C13 C14 117.07(19) . . ?
C5 C13 C15 111.90(18) . . ?
C12 C13 C5 99.86(19) . . ?
C12 C13 C14 108.30(18) . . ?
C12 C13 C15 109.55(19) . . ?
C14 C13 C15 109.55(19) . . ?
C8 C14 C9 110.96(18) . . ?
C8 C14 C13 108.45(19) . . ?
C8 C14 C18 109.46(18) . . ?
C13 C14 C9 105.96(18) . . ?
C13 C14 C18 110.21(18) . . ?
C18 C14 C9 111.7(2) . . ?
C13 C15 H15A 109.4 . . ?
C13 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C13 111.26(19) . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
N1 C16 C15 111.15(19) . . ?
N1 C16 H16A 109.4 . . ?
N1 C16 H16B 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.0 . . ?
C14 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 C14 113.06(18) . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.5(2) . . ?
C20 C19 H19 119.3 . . ?
O4 C20 C21 110.31(19) . . ?
C19 C20 O4 125.9(2) . . ?
C19 C20 C21 123.7(2) . . ?
F1 C21 F2 106.78(19) . . ?
F1 C21 F3 106.72(19) . . ?
F1 C21 C20 112.50(19) . . ?
F2 C21 F3 105.68(19) . . ?
F2 C21 C20 112.18(19) . . ?
F3 C21 C20 112.5(2) . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 O2 3.5(3) . . . . ?
O1 C3 C4 C12 -176.7(2) . . . . ?
O2 C4 C12 C11 173.0(2) . . . . ?
O2 C4 C12 C13 -4.6(3) . . . . ?
O2 C5 C6 O3 -64.2(2) . . . . ?
O2 C5 C6 C7 116.3(2) . . . . ?
O2 C5 C13 C12 -28.1(2) . . . . ?
O2 C5 C13 C14 -144.59(19) . . . . ?
O2 C5 C13 C15 87.8(2) . . . . ?
O3 C6 C7 C8 178.1(2) . . . . ?
O4 C8 C14 C9 68.5(2) . . . . ?
O4 C8 C14 C13 -175.48(17) . . . . ?
O4 C8 C14 C18 -55.2(2) . . . . ?
O4 C20 C21 F1 177.37(18) . . . . ?
O4 C20 C21 F2 57.0(3) . . . . ?
O4 C20 C21 F3 -62.1(3) . . . . ?
N1 C9 C10 C11 -87.4(2) . . . . ?
N1 C9 C14 C8 -177.93(18) . . . . ?
N1 C9 C14 C13 64.6(2) . . . . ?
N1 C9 C14 C18 -55.5(2) . . . . ?
C1 C2 C3 O1 -179.1(2) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C11 C12 C4 5.4(3) . . . . ?
C1 C11 C12 C13 -177.5(2) . . . . ?
C2 C1 C11 C10 174.4(2) . . . . ?
C2 C1 C11 C12 -0.9(3) . . . . ?
C2 C3 C4 O2 -176.5(2) . . . . ?
C2 C3 C4 C12 3.3(3) . . . . ?
C3 C4 C12 C11 -6.9(3) . . . . ?
C3 C4 C12 C13 175.6(2) . . . . ?
C4 O2 C5 C6 -94.6(2) . . . . ?
C4 O2 C5 C13 26.9(2) . . . . ?
C4 C12 C13 C5 20.3(2) . . . . ?
C4 C12 C13 C14 143.28(19) . . . . ?
C4 C12 C13 C15 -97.3(2) . . . . ?
C5 O2 C4 C3 165.4(2) . . . . ?
C5 O2 C4 C12 -14.4(2) . . . . ?
C5 C6 C7 C8 -2.4(4) . . . . ?
C5 C13 C14 C8 50.8(2) . . . . ?
C5 C13 C14 C9 170.02(19) . . . . ?
C5 C13 C14 C18 -69.0(3) . . . . ?
C5 C13 C15 C16 -173.11(18) . . . . ?
C6 C5 C13 C12 91.1(2) . . . . ?
C6 C5 C13 C14 -25.4(3) . . . . ?
C6 C5 C13 C15 -153.1(2) . . . . ?
C6 C7 C8 O4 155.3(2) . . . . ?
C6 C7 C8 C14 29.7(3) . . . . ?
C7 C8 C14 C9 -166.99(18) . . . . ?
C7 C8 C14 C13 -51.0(2) . . . . ?
C7 C8 C14 C18 69.3(2) . . . . ?
C8 O4 C20 C19 -19.4(3) . . . . ?
C8 O4 C20 C21 162.22(19) . . . . ?
C8 C14 C18 C19 36.2(3) . . . . ?
C9 N1 C16 C15 56.6(3) . . . . ?
C9 C10 C11 C1 178.0(2) . . . . ?
C9 C10 C11 C12 -6.8(3) . . . . ?
C9 C14 C18 C19 -87.1(2) . . . . ?
C10 C9 C14 C8 55.4(2) . . . . ?
C10 C9 C14 C13 -62.1(2) . . . . ?
C10 C9 C14 C18 177.82(18) . . . . ?
C10 C11 C12 C4 -170.4(2) . . . . ?
C10 C11 C12 C13 6.7(3) . . . . ?
C11 C1 C2 C3 -2.2(4) . . . . ?
C11 C12 C13 C5 -157.1(2) . . . . ?
C11 C12 C13 C14 -34.2(3) . . . . ?
C11 C12 C13 C15 85.3(3) . . . . ?
C12 C13 C14 C8 -61.0(2) . . . . ?
C12 C13 C14 C9 58.2(2) . . . . ?
C12 C13 C14 C18 179.22(19) . . . . ?
C12 C13 C15 C16 -63.3(3) . . . . ?
C13 C5 C6 O3 179.29(17) . . . . ?
C13 C5 C6 C7 -0.3(3) . . . . ?
C13 C14 C18 C19 155.4(2) . . . . ?
C13 C15 C16 N1 -51.0(3) . . . . ?
C14 C9 C10 C11 35.8(3) . . . . ?
C14 C13 C15 C16 55.3(3) . . . . ?
C14 C18 C19 C20 -10.2(3) . . . . ?
C15 C13 C14 C8 179.59(18) . . . . ?
C15 C13 C14 C9 -61.2(2) . . . . ?
C15 C13 C14 C18 59.8(2) . . . . ?
C16 N1 C9 C10 62.1(3) . . . . ?
C16 N1 C9 C14 -63.8(2) . . . . ?
C17 N1 C9 C10 -65.4(3) . . . . ?
C17 N1 C9 C14 168.58(18) . . . . ?
C17 N1 C16 C15 -174.45(19) . . . . ?
C18 C19 C20 O4 0.4(4) . . . . ?
C18 C19 C20 C21 178.6(2) . . . . ?
C19 C20 C21 F1 -1.1(4) . . . . ?
C19 C20 C21 F2 -121.5(3) . . . . ?
C19 C20 C21 F3 119.5(3) . . . . ?
C20 O4 C8 C7 -78.7(2) . . . . ?
C20 O4 C8 C14 47.1(3) . . . . ?
C22 O1 C3 C2 4.8(3) . . . . ?
C22 O1 C3 C4 -175.3(2) . . . . ?
C23 O3 C6 C5 177.16(18) . . . . ?
C23 O3 C6 C7 -3.3(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_38
_database_code_depnum_ccdc_archive 'CCDC 2291940'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-09-11 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT340_38                  
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01058 Ang.  
RESPONSE: The best crystal available was a small and thin needle.
;
# end Validation Reply Form

_audit_creation_date             2023-08-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H31 F2 N O4, H2 O, C2 H6 O'
_chemical_formula_sum            'C26 H39 F2 N O6'
_chemical_formula_weight         499.58
_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      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                   9.5587(9)
_cell_length_b                   10.1828(8)
_cell_length_c                   24.801(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2414.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.66
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1368 before and 0.0797 after correction.
The Ratio of minimum to maximum transmission is 0.8035.
The λ/2 correction factor is 0.0015.
;
_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    1.375
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1520
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            59479
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_min         1.642
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Quest D8'
_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         0.766
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4932
_reflns_number_total             5837
_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         0.443
_refine_diff_density_min         -0.608
_refine_diff_density_rms         0.116
_refine_ls_abs_structure_details 
;
 Flack x determined using 1821 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.33(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         5837
_refine_ls_number_restraints     101
_refine_ls_R_factor_all          0.1132
_refine_ls_R_factor_gt           0.0982
_refine_ls_restrained_S_all      1.146
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+14.5778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2272
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1S-C1S \\sim O1S-C1'S
 with sigma of 0.02
 O1S-C1S \\sim O1'S-C1'S
 with sigma of 0.02
 O1'S-H1'S \\sim O1S-H1S
 with sigma of 0.02
 C2S-C1S \\sim C2'S-C1'S
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq, Uanis(C24) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(O1S) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(O1) \\sim Ueq, Uanis(C23) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(C24)
\\sim Ueq, Uanis(C19) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(C22) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(C1S) \\sim Ueq, Uanis(C1'S) \\sim Ueq, Uanis(C2'S) \\sim Ueq, Uanis(C2S)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C12) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.1
Uanis(C4) \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
Uanis(O1S) = Uanis(O1'S)
Uanis(C1'S) = Uanis(C1S)
Uanis(C2'S) = Uanis(C2S)
4. Others
 Sof(O1S)=Sof(H1S)=Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=
 Sof(H2SC)=1-FVAR(1)
 Sof(O1'S)=Sof(H1'S)=Sof(C1'S)=Sof(H1'A)=Sof(H1'B)=Sof(C2'S)=Sof(H2'A)=
 Sof(H2'B)=Sof(H2'C)=FVAR(1)
5.a Riding coordinates:
 O4(H4), O2S(H2SD,H2SE), O1S(H1S), O1'S(H1'S)
5.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C22(H22)
5.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B),
 C19(H19A,H19B), C1S(H1SA,H1SB), C1'S(H1'A,H1'B)
5.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
5.e Idealised Me refined as rotating group:
 C17(H17A,H17C,H17B), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C2S(H2SA,H2SB,H2SC), C2'S(H2'A,H2'B,H2'C)
;
_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
F1 F 0.1700(6) 0.5556(5) 0.56768(17) 0.0320(12) Uani 1 1 d . . . . .
F2 F 0.1339(5) 0.3489(5) 0.58598(16) 0.0269(11) Uani 1 1 d . . . . .
O1 O 0.0044(8) 0.6966(6) 0.2360(2) 0.0335(15) Uani 1 1 d . U . . .
O2 O 0.1433(6) 0.6777(5) 0.34574(19) 0.0233(12) Uani 1 1 d . U . . .
O3 O 0.0582(6) 0.5513(5) 0.44560(18) 0.0195(11) Uani 1 1 d . . . . .
O4 O 0.2429(6) 0.2729(5) 0.48765(19) 0.0201(12) Uani 1 1 d . . . . .
H4 H 0.2346 0.2076 0.5094 0.024 Uiso 1 1 d R U . . .
N1 N 0.6721(7) 0.5214(6) 0.3546(2) 0.0174(13) Uani 1 1 d . . . . .
C1 C 0.3406(10) 0.5324(7) 0.2100(3) 0.0243(17) Uani 1 1 d . U . . .
H1 H 0.3845 0.4912 0.1801 0.029 Uiso 1 1 calc R U . . .
C2 C 0.2119(10) 0.5973(8) 0.2035(3) 0.0274(19) Uani 1 1 d . . . . .
H2 H 0.1734 0.6036 0.1683 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1382(10) 0.6529(7) 0.2464(3) 0.0247(18) Uani 1 1 d . . . . .
C4 C 0.2044(9) 0.6481(7) 0.2964(3) 0.0232(16) Uani 1 1 d . U . . .
C5 C 0.2467(8) 0.6390(7) 0.3876(3) 0.0166(15) Uani 1 1 d . . . . .
H5 H 0.2655 0.7154 0.4119 0.020 Uiso 1 1 calc R U . . .
C6 C 0.1907(8) 0.5219(6) 0.4213(2) 0.0161(14) Uani 1 1 d . . . . .
C7 C 0.3074(8) 0.4952(6) 0.4634(2) 0.0139(13) Uani 1 1 d . . . . .
H7 H 0.3286 0.5816 0.4808 0.017 Uiso 1 1 calc R U . . .
C8 C 0.4464(9) 0.4503(7) 0.4344(2) 0.0193(15) Uani 1 1 d . . . . .
H8A H 0.5248 0.5079 0.4454 0.023 Uiso 1 1 calc R U . . .
H8B H 0.4696 0.3591 0.4449 0.023 Uiso 1 1 calc R U . . .
C9 C 0.5572(8) 0.4324(7) 0.3382(3) 0.0170(14) Uani 1 1 d . . . . .
H9 H 0.5885 0.3406 0.3460 0.020 Uiso 1 1 calc R U . . .
C10 C 0.5229(9) 0.4397(7) 0.2759(3) 0.0200(15) Uani 1 1 d . U . . .
H10A H 0.6078 0.4697 0.2567 0.024 Uiso 1 1 calc R U . . .
H10B H 0.5010 0.3501 0.2630 0.024 Uiso 1 1 calc R U . . .
C11 C 0.4035(9) 0.5290(7) 0.2610(3) 0.0209(17) Uani 1 1 d . . . . .
C12 C 0.3367(9) 0.5979(7) 0.3011(3) 0.0211(16) Uani 1 1 d . U . . .
C13 C 0.3819(8) 0.5993(6) 0.3590(3) 0.0155(14) Uani 1 1 d . U . . .
C14 C 0.4248(9) 0.4586(7) 0.3730(3) 0.0168(15) Uani 1 1 d . . . . .
C15 C 0.4980(10) 0.6959(7) 0.3704(3) 0.0255(18) Uani 1 1 d . . . . .
H15A H 0.5120 0.7017 0.4098 0.031 Uiso 1 1 calc R U . . .
H15B H 0.4689 0.7838 0.3575 0.031 Uiso 1 1 calc R U . . .
C16 C 0.6375(9) 0.6597(7) 0.3437(3) 0.0207(16) Uani 1 1 d . . . . .
H16A H 0.6310 0.6739 0.3043 0.025 Uiso 1 1 calc R U . . .
H16B H 0.7126 0.7170 0.3579 0.025 Uiso 1 1 calc R U . . .
C17 C 0.8051(9) 0.4905(8) 0.3290(3) 0.0244(17) Uani 1 1 d . . . . .
H17A H 0.7998 0.5119 0.2905 0.037 Uiso 1 1 calc R U . . .
H17C H 0.8251 0.3967 0.3333 0.037 Uiso 1 1 calc R U . . .
H17B H 0.8797 0.5421 0.3458 0.037 Uiso 1 1 calc R U . . .
C18 C 0.1706(8) 0.4046(6) 0.3842(2) 0.0142(14) Uani 1 1 d . . . . .
H18A H 0.1057 0.4286 0.3546 0.017 Uiso 1 1 calc R U . . .
H18B H 0.1282 0.3313 0.4047 0.017 Uiso 1 1 calc R U . . .
C19 C 0.3110(8) 0.3601(6) 0.3602(3) 0.0149(13) Uani 1 1 d . U . . .
H19A H 0.3366 0.2733 0.3752 0.018 Uiso 1 1 calc R U . . .
H19B H 0.3018 0.3510 0.3206 0.018 Uiso 1 1 calc R U . . .
C20 C 0.2775(9) 0.3965(7) 0.5103(2) 0.0174(15) Uani 1 1 d . . . . .
C21 C 0.4019(9) 0.3858(8) 0.5483(3) 0.0220(16) Uani 1 1 d . . . . .
H21A H 0.3805 0.3228 0.5770 0.033 Uiso 1 1 calc R U . . .
H21B H 0.4213 0.4720 0.5642 0.033 Uiso 1 1 calc R U . . .
H21C H 0.4841 0.3558 0.5281 0.033 Uiso 1 1 calc R U . . .
C22 C 0.1495(9) 0.4361(7) 0.5439(3) 0.0205(15) Uani 1 1 d . U . . .
H22 H 0.0635 0.4376 0.5209 0.025 Uiso 1 1 calc R U . . .
C23 C -0.0448(12) 0.8085(8) 0.2666(3) 0.035(2) Uani 1 1 d . U . . .
H23A H -0.1322 0.8411 0.2509 0.052 Uiso 1 1 calc R U . . .
H23B H 0.0259 0.8782 0.2657 0.052 Uiso 1 1 calc R U . . .
H23C H -0.0614 0.7821 0.3041 0.052 Uiso 1 1 calc R U . . .
C24 C 0.0376(11) 0.6831(8) 0.4654(3) 0.033(2) Uani 1 1 d . U . . .
H24A H 0.1235 0.7137 0.4829 0.049 Uiso 1 1 calc R U . . .
H24B H -0.0394 0.6838 0.4914 0.049 Uiso 1 1 calc R U . . .
H24C H 0.0149 0.7413 0.4351 0.049 Uiso 1 1 calc R U . . .
O2S O 0.2918(6) 0.0486(5) 0.54627(18) 0.0208(11) Uani 1 1 d . . . . .
H2SD H 0.2695 0.0183 0.5736 0.025 Uiso 1 1 d R U . . .
H2SE H 0.3762 0.0440 0.5408 0.025 Uiso 1 1 d R U . . .
O1S O 0.2334(16) 0.9278(18) 0.4460(6) 0.028(3) Uani 0.515(11) 1 d D U P A 1
H1S H 0.2975 0.9432 0.4737 0.034 Uiso 0.515(11) 1 d DR U P A 1
C1S C 0.2825(19) 1.0205(14) 0.4074(5) 0.025(3) Uani 0.515(11) 1 d D U P A 1
H1SA H 0.3842 1.0088 0.4017 0.030 Uiso 0.515(11) 1 calc R U P A 1
H1SB H 0.2662 1.1108 0.4207 0.030 Uiso 0.515(11) 1 calc R U P A 1
C2S C 0.2064(18) 1.0005(15) 0.3552(5) 0.024(2) Uani 0.515(11) 1 d D U P A 1
H2SA H 0.2286 1.0727 0.3304 0.036 Uiso 0.515(11) 1 calc R U P A 1
H2SB H 0.1054 0.9988 0.3619 0.036 Uiso 0.515(11) 1 calc R U P A 1
H2SC H 0.2354 0.9171 0.3390 0.036 Uiso 0.515(11) 1 calc R U P A 1
O1'S O 0.2886(16) 0.944(2) 0.4390(7) 0.028(3) Uani 0.485(11) 1 d D . P A 2
H1'S H 0.2434 0.9593 0.4708 0.034 Uiso 0.485(11) 1 d DR U P A 2
C1'S C 0.211(2) 1.0119(16) 0.3978(6) 0.025(3) Uani 0.485(11) 1 d D U P A 2
H1'A H 0.1964 1.1043 0.4090 0.030 Uiso 0.485(11) 1 calc R U P A 2
H1'B H 0.1182 0.9703 0.3936 0.030 Uiso 0.485(11) 1 calc R U P A 2
C2'S C 0.2871(19) 1.0091(16) 0.3444(6) 0.024(2) Uani 0.485(11) 1 d D U P A 2
H2'A H 0.2410 1.0691 0.3191 0.036 Uiso 0.485(11) 1 calc R U P A 2
H2'B H 0.2852 0.9197 0.3298 0.036 Uiso 0.485(11) 1 calc R U P A 2
H2'C H 0.3844 1.0367 0.3497 0.036 Uiso 0.485(11) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C22 1.366(8) . ?
F2 C22 1.379(8) . ?
O1 C3 1.378(11) . ?
O1 C23 1.449(10) . ?
O2 C4 1.389(9) . ?
O2 C5 1.486(8) . ?
O3 C6 1.435(9) . ?
O3 C24 1.442(9) . ?
O4 H4 0.8604 . ?
O4 C20 1.418(8) . ?
N1 C9 1.481(9) . ?
N1 C16 1.472(9) . ?
N1 C17 1.456(10) . ?
C1 H1 0.9500 . ?
C1 C2 1.406(12) . ?
C1 C11 1.400(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.397(11) . ?
C3 C4 1.394(10) . ?
C4 C12 1.369(12) . ?
C5 H5 1.0000 . ?
C5 C6 1.552(9) . ?
C5 C13 1.528(10) . ?
C6 C7 1.553(10) . ?
C6 C18 1.520(9) . ?
C7 H7 1.0000 . ?
C7 C8 1.578(10) . ?
C7 C20 1.564(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.540(9) . ?
C9 H9 1.0000 . ?
C9 C10 1.580(9) . ?
C9 C14 1.556(10) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.505(11) . ?
C11 C12 1.376(10) . ?
C12 C13 1.499(9) . ?
C13 C14 1.530(9) . ?
C13 C15 1.509(11) . ?
C14 C19 1.513(10) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.533(12) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17B 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.536(10) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.520(11) . ?
C20 C22 1.534(10) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O2S H2SD 0.7755 . ?
O2S H2SE 0.8192 . ?
O1S H1S 0.9341 . ?
O1S C1S 1.424(16) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C1S C2S 1.499(18) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
O1'S H1'S 0.9130 . ?
O1'S C1'S 1.439(18) . ?
C1'S H1'A 0.9900 . ?
C1'S H1'B 0.9900 . ?
C1'S C2'S 1.511(17) . ?
C2'S H2'A 0.9800 . ?
C2'S H2'B 0.9800 . ?
C2'S H2'C 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
C3 O1 C23 117.2(7) . . ?
C4 O2 C5 106.1(6) . . ?
C6 O3 C24 117.2(6) . . ?
C20 O4 H4 117.4 . . ?
C16 N1 C9 111.6(6) . . ?
C17 N1 C9 113.2(5) . . ?
C17 N1 C16 108.8(6) . . ?
C2 C1 H1 120.3 . . ?
C11 C1 H1 120.3 . . ?
C11 C1 C2 119.5(7) . . ?
C1 C2 H2 118.5 . . ?
C3 C2 C1 122.9(7) . . ?
C3 C2 H2 118.5 . . ?
O1 C3 C2 117.2(7) . . ?
O1 C3 C4 126.8(7) . . ?
C4 C3 C2 115.8(8) . . ?
O2 C4 C3 125.8(8) . . ?
C12 C4 O2 113.2(6) . . ?
C12 C4 C3 120.6(7) . . ?
O2 C5 H5 109.5 . . ?
O2 C5 C6 110.5(6) . . ?
O2 C5 C13 108.0(5) . . ?
C6 C5 H5 109.5 . . ?
C13 C5 H5 109.5 . . ?
C13 C5 C6 109.7(6) . . ?
O3 C6 C5 111.8(5) . . ?
O3 C6 C7 112.8(5) . . ?
O3 C6 C18 107.9(6) . . ?
C5 C6 C7 104.4(6) . . ?
C18 C6 C5 108.8(5) . . ?
C18 C6 C7 111.2(5) . . ?
C6 C7 H7 106.3 . . ?
C6 C7 C8 110.4(5) . . ?
C6 C7 C20 118.8(6) . . ?
C8 C7 H7 106.3 . . ?
C20 C7 H7 106.3 . . ?
C20 C7 C8 107.9(5) . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
C14 C8 C7 108.8(6) . . ?
C14 C8 H8A 109.9 . . ?
C14 C8 H8B 109.9 . . ?
N1 C9 H9 107.2 . . ?
N1 C9 C10 113.2(6) . . ?
N1 C9 C14 110.2(5) . . ?
C10 C9 H9 107.2 . . ?
C14 C9 H9 107.2 . . ?
C14 C9 C10 111.4(6) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 115.3(6) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C1 C11 C10 124.3(6) . . ?
C12 C11 C1 116.2(7) . . ?
C12 C11 C10 118.8(6) . . ?
C4 C12 C11 123.9(7) . . ?
C4 C12 C13 110.2(6) . . ?
C11 C12 C13 124.3(7) . . ?
C5 C13 C14 111.7(6) . . ?
C12 C13 C5 101.7(6) . . ?
C12 C13 C14 106.6(5) . . ?
C12 C13 C15 113.4(6) . . ?
C15 C13 C5 111.2(6) . . ?
C15 C13 C14 111.8(6) . . ?
C8 C14 C9 115.5(6) . . ?
C13 C14 C8 108.1(5) . . ?
C13 C14 C9 104.6(6) . . ?
C19 C14 C8 105.6(6) . . ?
C19 C14 C9 110.8(5) . . ?
C19 C14 C13 112.4(6) . . ?
C13 C15 H15A 108.8 . . ?
C13 C15 H15B 108.8 . . ?
C13 C15 C16 113.7(6) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
N1 C16 C15 110.3(6) . . ?
N1 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17C 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?
C6 C18 H18A 109.5 . . ?
C6 C18 H18B 109.5 . . ?
C6 C18 C19 110.8(6) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C14 C19 C18 110.6(5) . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
O4 C20 C7 108.5(5) . . ?
O4 C20 C21 111.4(6) . . ?
O4 C20 C22 105.2(6) . . ?
C21 C20 C7 111.3(6) . . ?
C21 C20 C22 107.9(5) . . ?
C22 C20 C7 112.4(6) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F1 C22 F2 105.2(5) . . ?
F1 C22 C20 110.8(6) . . ?
F1 C22 H22 110.5 . . ?
F2 C22 C20 109.1(6) . . ?
F2 C22 H22 110.5 . . ?
C20 C22 H22 110.5 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H2SD O2S H2SE 113.2 . . ?
C1S O1S H1S 99.7 . . ?
O1S C1S H1SA 109.8 . . ?
O1S C1S H1SB 109.8 . . ?
O1S C1S C2S 109.4(14) . . ?
H1SA C1S H1SB 108.3 . . ?
C2S C1S H1SA 109.8 . . ?
C2S C1S H1SB 109.8 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1'S O1'S H1'S 106.8 . . ?
O1'S C1'S H1'A 109.3 . . ?
O1'S C1'S H1'B 109.3 . . ?
O1'S C1'S C2'S 111.5(15) . . ?
H1'A C1'S H1'B 108.0 . . ?
C2'S C1'S H1'A 109.3 . . ?
C2'S C1'S H1'B 109.3 . . ?
C1'S C2'S H2'A 109.5 . . ?
C1'S C2'S H2'B 109.5 . . ?
C1'S C2'S H2'C 109.5 . . ?
H2'A C2'S H2'B 109.5 . . ?
H2'A C2'S H2'C 109.5 . . ?
H2'B C2'S H2'C 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 C3 C4 O2 5.1(13) . . . . ?
O1 C3 C4 C12 177.7(8) . . . . ?
O2 C4 C12 C11 161.6(7) . . . . ?
O2 C4 C12 C13 -4.5(9) . . . . ?
O2 C5 C6 O3 -56.6(7) . . . . ?
O2 C5 C6 C7 -178.9(5) . . . . ?
O2 C5 C6 C18 62.4(7) . . . . ?
O2 C5 C13 C12 -8.8(7) . . . . ?
O2 C5 C13 C14 -122.1(6) . . . . ?
O2 C5 C13 C15 112.2(6) . . . . ?
O3 C6 C7 C8 174.6(5) . . . . ?
O3 C6 C7 C20 49.3(8) . . . . ?
O3 C6 C18 C19 -175.3(5) . . . . ?
O4 C20 C22 F1 -179.5(5) . . . . ?
O4 C20 C22 F2 65.2(7) . . . . ?
N1 C9 C10 C11 -96.4(8) . . . . ?
N1 C9 C14 C8 -54.9(8) . . . . ?
N1 C9 C14 C13 63.9(7) . . . . ?
N1 C9 C14 C19 -174.8(5) . . . . ?
C1 C2 C3 O1 -170.7(7) . . . . ?
C1 C2 C3 C4 4.1(12) . . . . ?
C1 C11 C12 C4 11.7(11) . . . . ?
C1 C11 C12 C13 175.8(7) . . . . ?
C2 C1 C11 C10 166.2(7) . . . . ?
C2 C1 C11 C12 -3.8(11) . . . . ?
C2 C3 C4 O2 -169.1(7) . . . . ?
C2 C3 C4 C12 3.5(11) . . . . ?
C3 C4 C12 C11 -11.9(12) . . . . ?
C3 C4 C12 C13 -177.9(7) . . . . ?
C4 O2 C5 C6 -113.3(6) . . . . ?
C4 O2 C5 C13 6.7(7) . . . . ?
C4 C12 C13 C5 8.1(8) . . . . ?
C4 C12 C13 C14 125.2(7) . . . . ?
C4 C12 C13 C15 -111.4(7) . . . . ?
C5 O2 C4 C3 171.5(7) . . . . ?
C5 O2 C4 C12 -1.5(8) . . . . ?
C5 C6 C7 C8 -63.8(6) . . . . ?
C5 C6 C7 C20 170.8(5) . . . . ?
C5 C6 C18 C19 63.3(7) . . . . ?
C5 C13 C14 C8 -59.7(8) . . . . ?
C5 C13 C14 C9 176.7(6) . . . . ?
C5 C13 C14 C19 56.4(7) . . . . ?
C5 C13 C15 C16 178.8(6) . . . . ?
C6 C5 C13 C12 111.7(6) . . . . ?
C6 C5 C13 C14 -1.6(8) . . . . ?
C6 C5 C13 C15 -127.3(6) . . . . ?
C6 C7 C8 C14 4.7(8) . . . . ?
C6 C7 C20 O4 58.6(8) . . . . ?
C6 C7 C20 C21 -178.4(6) . . . . ?
C6 C7 C20 C22 -57.3(8) . . . . ?
C6 C18 C19 C14 -9.2(7) . . . . ?
C7 C6 C18 C19 -51.1(7) . . . . ?
C7 C8 C14 C9 173.5(6) . . . . ?
C7 C8 C14 C13 56.7(8) . . . . ?
C7 C8 C14 C19 -63.7(7) . . . . ?
C7 C20 C22 F1 -61.6(8) . . . . ?
C7 C20 C22 F2 -176.9(6) . . . . ?
C8 C7 C20 O4 -67.9(8) . . . . ?
C8 C7 C20 C21 55.0(7) . . . . ?
C8 C7 C20 C22 176.1(6) . . . . ?
C8 C14 C19 C18 67.6(7) . . . . ?
C9 N1 C16 C15 54.5(7) . . . . ?
C9 C10 C11 C1 -168.3(7) . . . . ?
C9 C10 C11 C12 1.3(10) . . . . ?
C9 C14 C19 C18 -166.7(5) . . . . ?
C10 C9 C14 C8 178.6(6) . . . . ?
C10 C9 C14 C13 -62.6(7) . . . . ?
C10 C9 C14 C19 58.7(7) . . . . ?
C10 C11 C12 C4 -158.8(7) . . . . ?
C10 C11 C12 C13 5.3(12) . . . . ?
C11 C1 C2 C3 -3.9(12) . . . . ?
C11 C12 C13 C5 -157.9(7) . . . . ?
C11 C12 C13 C14 -40.8(10) . . . . ?
C11 C12 C13 C15 82.6(9) . . . . ?
C12 C13 C14 C8 -169.9(7) . . . . ?
C12 C13 C14 C9 66.5(7) . . . . ?
C12 C13 C14 C19 -53.8(7) . . . . ?
C12 C13 C15 C16 -67.4(8) . . . . ?
C13 C5 C6 O3 -175.6(5) . . . . ?
C13 C5 C6 C7 62.1(6) . . . . ?
C13 C5 C6 C18 -56.6(8) . . . . ?
C13 C14 C19 C18 -50.1(7) . . . . ?
C13 C15 C16 N1 -49.0(8) . . . . ?
C14 C9 C10 C11 28.5(9) . . . . ?
C14 C13 C15 C16 53.1(7) . . . . ?
C15 C13 C14 C8 65.7(8) . . . . ?
C15 C13 C14 C9 -57.9(7) . . . . ?
C15 C13 C14 C19 -178.2(5) . . . . ?
C16 N1 C9 C10 60.8(7) . . . . ?
C16 N1 C9 C14 -64.8(7) . . . . ?
C17 N1 C9 C10 -62.4(8) . . . . ?
C17 N1 C9 C14 172.1(5) . . . . ?
C17 N1 C16 C15 -179.8(6) . . . . ?
C18 C6 C7 C8 53.3(7) . . . . ?
C18 C6 C7 C20 -72.1(7) . . . . ?
C20 C7 C8 C14 136.0(6) . . . . ?
C21 C20 C22 F1 61.5(7) . . . . ?
C21 C20 C22 F2 -53.8(8) . . . . ?
C23 O1 C3 C2 -148.4(7) . . . . ?
C23 O1 C3 C4 37.4(11) . . . . ?
C24 O3 C6 C5 -37.5(8) . . . . ?
C24 O3 C6 C7 79.8(7) . . . . ?
C24 O3 C6 C18 -157.0(6) . . . . ?

_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_26
_database_code_depnum_ccdc_archive 'CCDC 2291939'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-09-12 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H29 F2 N O4'
_chemical_formula_sum            'C23 H29 F2 N O4'
_chemical_formula_weight         421.47
_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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   12.2544(3)
_cell_length_b                   24.9923(7)
_cell_length_c                   7.2291(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2214.02(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.59
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1567 before and 0.0926 after correction.
The Ratio of minimum to maximum transmission is 0.7195.
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    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            29109
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.988
_diffrn_reflns_theta_min         2.328
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5619
_reflns_number_total             5876
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         5876
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0373
_refine_ls_restrained_S_all      1.028
_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)+(0.0543P)²+0.2800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.0967
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6(6)
 0.4(6)
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. Others
 Sof(H21A)=Sof(F3)=1-FVAR(1)
 Sof(H21)=Sof(F2)=FVAR(1)
4.a Riding coordinates:
 O4(H4)
4.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C20(H20), C21(H21), C21(H21A)
4.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B),
 C19(H19A,H19B)
4.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
4.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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
F1 F 0.34873(12) 0.40260(5) 0.86855(18) 0.0332(3) Uani 1 1 d . . . . .
O1 O 0.55557(9) 0.30521(4) 0.12570(18) 0.0130(2) Uani 1 1 d . . . . .
O2 O 0.66039(10) 0.22488(4) -0.08563(18) 0.0158(3) Uani 1 1 d . . . . .
O3 O 0.43647(9) 0.29727(4) 0.46092(18) 0.0143(2) Uani 1 1 d . . . . .
O4 O 0.39891(10) 0.44304(5) 0.39987(18) 0.0162(2) Uani 1 1 d . . . . .
H4 H 0.3404 0.4646 0.3941 0.019 Uiso 1 1 d R U . . .
N1 N 0.75995(11) 0.48448(5) 0.2977(2) 0.0133(3) Uani 1 1 d . . . . .
C1 C 0.88614(13) 0.31889(7) 0.0353(3) 0.0158(3) Uani 1 1 d . . . . .
H1 H 0.9633 0.3213 0.0267 0.019 Uiso 1 1 calc R U . . .
C2 C 0.83216(13) 0.27535(6) -0.0464(2) 0.0143(3) Uani 1 1 d . . . . .
H2 H 0.8729 0.2503 -0.1171 0.017 Uiso 1 1 calc R U . . .
C3 C 0.71935(13) 0.26814(6) -0.0259(2) 0.0127(3) Uani 1 1 d . . . . .
C4 C 0.66310(12) 0.30769(6) 0.0697(2) 0.0120(3) Uani 1 1 d . . . . .
C5 C 0.53780(13) 0.35040(6) 0.2532(2) 0.0111(3) Uani 1 1 d . . . . .
H5 H 0.4706 0.3704 0.2164 0.013 Uiso 1 1 calc R U . . .
C6 C 0.52858(13) 0.33250(6) 0.4552(2) 0.0105(3) Uani 1 1 d . . . . .
C7 C 0.51218(13) 0.38301(6) 0.5792(2) 0.0111(3) Uani 1 1 d . . . . .
H7 H 0.5161 0.3704 0.7104 0.013 Uiso 1 1 calc R U . A 2
C8 C 0.60769(13) 0.42391(6) 0.5528(2) 0.0114(3) Uani 1 1 d . . . . .
H8A H 0.5797 0.4574 0.4972 0.014 Uiso 1 1 calc R U . . .
H8B H 0.6408 0.4326 0.6740 0.014 Uiso 1 1 calc R U . . .
C9 C 0.79536(13) 0.43288(6) 0.3792(2) 0.0125(3) Uani 1 1 d . . . . .
H9 H 0.8333 0.4410 0.4985 0.015 Uiso 1 1 calc R U . . .
C10 C 0.87834(13) 0.40144(6) 0.2526(3) 0.0147(3) Uani 1 1 d . . . . .
H10A H 0.9170 0.4276 0.1733 0.018 Uiso 1 1 calc R U . . .
H10B H 0.9335 0.3843 0.3331 0.018 Uiso 1 1 calc R U . . .
C11 C 0.82840(13) 0.35862(6) 0.1287(2) 0.0130(3) Uani 1 1 d . . . . .
C12 C 0.71593(13) 0.35275(6) 0.1321(2) 0.0116(3) Uani 1 1 d . . . . .
C13 C 0.63858(12) 0.38732(6) 0.2367(2) 0.0106(3) Uani 1 1 d . . . . .
C14 C 0.69350(13) 0.39853(6) 0.4251(2) 0.0105(3) Uani 1 1 d . . . . .
C15 C 0.61091(13) 0.43918(6) 0.1319(2) 0.0127(3) Uani 1 1 d . . . . .
H15A H 0.5844 0.4300 0.0065 0.015 Uiso 1 1 calc R U . . .
H15B H 0.5513 0.4580 0.1975 0.015 Uiso 1 1 calc R U . . .
C16 C 0.70918(14) 0.47646(6) 0.1155(3) 0.0151(3) Uani 1 1 d . . . . .
H16A H 0.7632 0.4608 0.0292 0.018 Uiso 1 1 calc R U . . .
H16B H 0.6855 0.5114 0.0649 0.018 Uiso 1 1 calc R U . . .
C17 C 0.84928(14) 0.52345(6) 0.2836(3) 0.0188(4) Uani 1 1 d . . . . .
H17A H 0.9000 0.5123 0.1861 0.028 Uiso 1 1 calc R U . . .
H17B H 0.8881 0.5253 0.4019 0.028 Uiso 1 1 calc R U . . .
H17C H 0.8193 0.5587 0.2534 0.028 Uiso 1 1 calc R U . . .
C18 C 0.63436(13) 0.30502(6) 0.5156(2) 0.0126(3) Uani 1 1 d . . . . .
H18A H 0.6528 0.2761 0.4273 0.015 Uiso 1 1 calc R U . . .
H18B H 0.6244 0.2888 0.6394 0.015 Uiso 1 1 calc R U . . .
C19 C 0.72803(13) 0.34627(6) 0.5221(2) 0.0130(3) Uani 1 1 d . . . . .
H19A H 0.7473 0.3539 0.6525 0.016 Uiso 1 1 calc R U . . .
H19B H 0.7933 0.3313 0.4601 0.016 Uiso 1 1 calc R U . . .
C20 C 0.39852(13) 0.40833(6) 0.5540(2) 0.0122(3) Uani 1 1 d . . . . .
H20 H 0.3448 0.3790 0.5300 0.015 Uiso 1 1 calc R U . . .
C21 C 0.36328(15) 0.43801(6) 0.7264(3) 0.0174(3) Uani 1 1 d . . . . .
H21 H 0.4198 0.4651 0.7610 0.021 Uiso 0.520(4) 1 calc R U P B 1
H21A H 0.2935 0.4575 0.7019 0.021 Uiso 0.480(4) 1 calc R U P B 2
C22 C 0.71941(16) 0.18390(7) -0.1801(3) 0.0238(4) Uani 1 1 d . . . . .
H22A H 0.7734 0.1682 -0.0961 0.036 Uiso 1 1 calc R U . . .
H22B H 0.7567 0.1993 -0.2875 0.036 Uiso 1 1 calc R U . . .
H22C H 0.6686 0.1561 -0.2214 0.036 Uiso 1 1 calc R U . . .
C23 C 0.41328(15) 0.27312(7) 0.6345(3) 0.0211(4) Uani 1 1 d . . . . .
H23A H 0.4147 0.3005 0.7316 0.032 Uiso 1 1 calc R U . . .
H23B H 0.4683 0.2457 0.6612 0.032 Uiso 1 1 calc R U . . .
H23C H 0.3409 0.2565 0.6302 0.032 Uiso 1 1 calc R U . . .
F2 F 0.26912(16) 0.46147(8) 0.7027(3) 0.0189(6) Uani 0.520(4) 1 d . . P B 1
F3 F 0.43497(16) 0.47078(8) 0.7917(3) 0.0161(6) Uani 0.480(4) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C21 1.368(2) . ?
O1 C4 1.3799(19) . ?
O1 C5 1.4739(18) . ?
O2 C3 1.3702(19) . ?
O2 C22 1.428(2) . ?
O3 C6 1.4322(18) . ?
O3 C23 1.421(2) . ?
O4 H4 0.8975 . ?
O4 C20 1.412(2) . ?
N1 C9 1.483(2) . ?
N1 C16 1.470(2) . ?
N1 C17 1.469(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.404(2) . ?
C1 C11 1.394(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.402(2) . ?
C3 C4 1.389(2) . ?
C4 C12 1.375(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.531(2) . ?
C5 C13 1.546(2) . ?
C6 C7 1.562(2) . ?
C6 C18 1.531(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.566(2) . ?
C7 C20 1.541(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.536(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.578(2) . ?
C9 C14 1.551(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.524(2) . ?
C11 C12 1.386(2) . ?
C12 C13 1.489(2) . ?
C13 C14 1.545(2) . ?
C13 C15 1.539(2) . ?
C14 C19 1.542(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.527(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.544(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20 1.0000 . ?
C20 C21 1.513(2) . ?
C21 H21 1.0000 . ?
C21 H21A 1.0000 . ?
C21 F2 1.306(3) . ?
C21 F3 1.290(3) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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 106.86(11) . . ?
C3 O2 C22 116.72(14) . . ?
C23 O3 C6 116.39(13) . . ?
C20 O4 H4 113.7 . . ?
C16 N1 C9 111.19(12) . . ?
C17 N1 C9 112.71(13) . . ?
C17 N1 C16 110.11(14) . . ?
C2 C1 H1 119.4 . . ?
C11 C1 H1 119.4 . . ?
C11 C1 C2 121.13(15) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.32(15) . . ?
C3 C2 H2 119.3 . . ?
O2 C3 C2 126.02(15) . . ?
O2 C3 C4 117.17(14) . . ?
C4 C3 C2 116.77(15) . . ?
O1 C4 C3 126.00(14) . . ?
C12 C4 O1 112.98(14) . . ?
C12 C4 C3 120.81(15) . . ?
O1 C5 H5 109.8 . . ?
O1 C5 C6 112.54(12) . . ?
O1 C5 C13 106.93(12) . . ?
C6 C5 H5 109.8 . . ?
C6 C5 C13 107.87(13) . . ?
C13 C5 H5 109.8 . . ?
O3 C6 C5 105.40(13) . . ?
O3 C6 C7 112.26(13) . . ?
O3 C6 C18 112.53(12) . . ?
C5 C6 C7 108.73(12) . . ?
C18 C6 C5 109.92(13) . . ?
C18 C6 C7 107.93(13) . . ?
C6 C7 H7 106.5 . . ?
C6 C7 C8 111.19(13) . . ?
C8 C7 H7 106.5 . . ?
C20 C7 C6 112.37(13) . . ?
C20 C7 H7 106.5 . . ?
C20 C7 C8 113.15(12) . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
C14 C8 C7 108.39(12) . . ?
C14 C8 H8A 110.0 . . ?
C14 C8 H8B 110.0 . . ?
N1 C9 H9 107.6 . . ?
N1 C9 C10 113.02(14) . . ?
N1 C9 C14 109.33(12) . . ?
C10 C9 H9 107.6 . . ?
C14 C9 H9 107.6 . . ?
C14 C9 C10 111.54(12) . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 115.59(13) . . ?
C11 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C1 C11 C10 125.54(15) . . ?
C12 C11 C1 115.96(15) . . ?
C12 C11 C10 117.60(15) . . ?
C4 C12 C11 123.30(15) . . ?
C4 C12 C13 110.00(14) . . ?
C11 C12 C13 125.48(15) . . ?
C12 C13 C5 101.61(12) . . ?
C12 C13 C14 106.02(13) . . ?
C12 C13 C15 112.27(14) . . ?
C14 C13 C5 112.83(13) . . ?
C15 C13 C5 111.38(12) . . ?
C15 C13 C14 112.16(13) . . ?
C8 C14 C9 116.80(12) . . ?
C8 C14 C13 107.85(12) . . ?
C8 C14 C19 105.34(13) . . ?
C13 C14 C9 105.21(13) . . ?
C19 C14 C9 110.21(12) . . ?
C19 C14 C13 111.52(12) . . ?
C13 C15 H15A 109.2 . . ?
C13 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C13 112.23(13) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
N1 C16 C15 110.31(13) . . ?
N1 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C18 H18A 109.7 . . ?
C6 C18 H18B 109.7 . . ?
C6 C18 C19 109.80(12) . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
C14 C19 C18 110.36(13) . . ?
C14 C19 H19A 109.6 . . ?
C14 C19 H19B 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
O4 C20 C7 110.03(13) . . ?
O4 C20 H20 108.3 . . ?
O4 C20 C21 110.47(12) . . ?
C7 C20 H20 108.3 . . ?
C21 C20 C7 111.23(14) . . ?
C21 C20 H20 108.3 . . ?
F1 C21 C20 109.80(13) . . ?
F1 C21 H21 109.9 . . ?
F1 C21 H21A 109.7 . . ?
C20 C21 H21 109.9 . . ?
C20 C21 H21A 109.7 . . ?
F2 C21 F1 105.90(17) . . ?
F2 C21 C20 111.36(17) . . ?
F2 C21 H21 109.9 . . ?
F3 C21 F1 102.96(17) . . ?
F3 C21 C20 114.72(17) . . ?
F3 C21 H21A 109.7 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 C12 C11 165.52(16) . . . . ?
O1 C4 C12 C13 -2.46(19) . . . . ?
O1 C5 C6 O3 -60.51(16) . . . . ?
O1 C5 C6 C7 178.94(12) . . . . ?
O1 C5 C6 C18 60.99(16) . . . . ?
O1 C5 C13 C12 -12.49(16) . . . . ?
O1 C5 C13 C14 -125.58(13) . . . . ?
O1 C5 C13 C15 107.24(14) . . . . ?
O2 C3 C4 O1 6.6(2) . . . . ?
O2 C3 C4 C12 -179.05(15) . . . . ?
O3 C6 C7 C8 -173.42(13) . . . . ?
O3 C6 C7 C20 -45.43(17) . . . . ?
O3 C6 C18 C19 -175.20(13) . . . . ?
O4 C20 C21 F1 171.69(14) . . . . ?
O4 C20 C21 F2 54.7(2) . . . . ?
O4 C20 C21 F3 -73.0(2) . . . . ?
N1 C9 C10 C11 -96.26(16) . . . . ?
N1 C9 C14 C8 -56.11(19) . . . . ?
N1 C9 C14 C13 63.44(15) . . . . ?
N1 C9 C14 C19 -176.22(13) . . . . ?
C1 C2 C3 O2 -173.93(16) . . . . ?
C1 C2 C3 C4 3.6(2) . . . . ?
C1 C11 C12 C4 8.2(2) . . . . ?
C1 C11 C12 C13 174.35(16) . . . . ?
C2 C1 C11 C10 167.67(16) . . . . ?
C2 C1 C11 C12 -1.2(2) . . . . ?
C2 C3 C4 O1 -171.17(16) . . . . ?
C2 C3 C4 C12 3.2(2) . . . . ?
C3 C4 C12 C11 -9.5(3) . . . . ?
C3 C4 C12 C13 -177.49(15) . . . . ?
C4 O1 C5 C6 -106.56(14) . . . . ?
C4 O1 C5 C13 11.70(16) . . . . ?
C4 C12 C13 C5 9.25(17) . . . . ?
C4 C12 C13 C14 127.36(14) . . . . ?
C4 C12 C13 C15 -109.85(15) . . . . ?
C5 O1 C4 C3 168.67(16) . . . . ?
C5 O1 C4 C12 -6.05(18) . . . . ?
C5 C6 C7 C8 -57.21(17) . . . . ?
C5 C6 C7 C20 70.79(16) . . . . ?
C5 C6 C18 C19 67.66(16) . . . . ?
C5 C13 C14 C8 -57.95(16) . . . . ?
C5 C13 C14 C9 176.71(12) . . . . ?
C5 C13 C14 C19 57.25(16) . . . . ?
C5 C13 C15 C16 179.52(14) . . . . ?
C6 C5 C13 C12 108.78(14) . . . . ?
C6 C5 C13 C14 -4.31(16) . . . . ?
C6 C5 C13 C15 -131.49(14) . . . . ?
C6 C7 C8 C14 -5.28(18) . . . . ?
C6 C7 C20 O4 -84.21(15) . . . . ?
C6 C7 C20 C21 153.04(13) . . . . ?
C6 C18 C19 C14 -12.78(19) . . . . ?
C7 C6 C18 C19 -50.77(17) . . . . ?
C7 C8 C14 C9 179.47(13) . . . . ?
C7 C8 C14 C13 61.35(16) . . . . ?
C7 C8 C14 C19 -57.86(16) . . . . ?
C7 C20 C21 F1 -65.81(18) . . . . ?
C7 C20 C21 F2 177.23(15) . . . . ?
C7 C20 C21 F3 49.5(2) . . . . ?
C8 C7 C20 O4 42.75(17) . . . . ?
C8 C7 C20 C21 -80.01(16) . . . . ?
C8 C14 C19 C18 70.16(16) . . . . ?
C9 N1 C16 C15 58.55(17) . . . . ?
C9 C10 C11 C1 -165.98(16) . . . . ?
C9 C10 C11 C12 2.7(2) . . . . ?
C9 C14 C19 C18 -163.03(14) . . . . ?
C10 C9 C14 C8 178.17(14) . . . . ?
C10 C9 C14 C13 -62.29(16) . . . . ?
C10 C9 C14 C19 58.05(18) . . . . ?
C10 C11 C12 C4 -161.53(15) . . . . ?
C10 C11 C12 C13 4.6(2) . . . . ?
C11 C1 C2 C3 -4.7(3) . . . . ?
C11 C12 C13 C5 -158.41(16) . . . . ?
C11 C12 C13 C14 -40.3(2) . . . . ?
C11 C12 C13 C15 82.5(2) . . . . ?
C12 C13 C14 C8 -168.32(12) . . . . ?
C12 C13 C14 C9 66.34(14) . . . . ?
C12 C13 C14 C19 -53.13(16) . . . . ?
C12 C13 C15 C16 -67.29(17) . . . . ?
C13 C5 C6 O3 -178.22(11) . . . . ?
C13 C5 C6 C7 61.23(15) . . . . ?
C13 C5 C6 C18 -56.72(15) . . . . ?
C13 C14 C19 C18 -46.57(18) . . . . ?
C13 C15 C16 N1 -50.63(18) . . . . ?
C14 C9 C10 C11 27.4(2) . . . . ?
C14 C13 C15 C16 51.97(18) . . . . ?
C15 C13 C14 C8 68.82(16) . . . . ?
C15 C13 C14 C9 -56.52(16) . . . . ?
C15 C13 C14 C19 -175.99(13) . . . . ?
C16 N1 C9 C10 57.89(17) . . . . ?
C16 N1 C9 C14 -66.98(17) . . . . ?
C17 N1 C9 C10 -66.30(18) . . . . ?
C17 N1 C9 C14 168.83(14) . . . . ?
C17 N1 C16 C15 -175.80(13) . . . . ?
C18 C6 C7 C8 61.99(16) . . . . ?
C18 C6 C7 C20 -170.01(13) . . . . ?
C20 C7 C8 C14 -132.85(14) . . . . ?
C22 O2 C3 C2 -1.1(2) . . . . ?
C22 O2 C3 C4 -178.63(16) . . . . ?
C23 O3 C6 C5 177.38(13) . . . . ?
C23 O3 C6 C7 -64.41(17) . . . . ?
C23 O3 C6 C18 57.59(18) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.726 211.5 46.7 '2.5 MeOH'
2 0.500 0.000 0.274 211.5 46.7 '2.5 MeOH'

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6(6)
2 0.4(6)

####################################################################### 
# 
# 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_41
_database_code_depnum_ccdc_archive 'CCDC 2291938'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-09-11 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_audit_creation_date             2023-08-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H35 F2 N O4, H2 O'
_chemical_formula_sum            'C26 H37 F2 N O5'
_chemical_formula_weight         481.56
_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      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                   9.4825(3)
_cell_length_b                   12.4436(4)
_cell_length_c                   19.8848(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2346.33(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9334
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.73
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1124 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.7449.
The λ/2 correction factor is 0.0015.
;
_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    1.363
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29168
_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         28.000
_diffrn_reflns_theta_min         1.931
_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 Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4926
_reflns_number_total             5664
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1919 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(4)
_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     311
_refine_ls_number_reflns         5664
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0382
_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)+(0.0389P)²+0.3767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0888
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups, All O(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O4(H4), O1S(H1SB,H1SA)
2.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C21(H21)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B),
 C19(H19A,H19B), C22(H22A,H22B), C23(H23A,H23B)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
;
_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
F1 F 0.40177(15) 0.15348(12) 0.65565(7) 0.0236(3) Uani 1 1 d . . . . .
F2 F 0.39502(15) 0.09180(11) 0.55296(7) 0.0226(3) Uani 1 1 d . . . . .
O1 O 0.22634(18) 0.79014(15) 0.69505(9) 0.0230(4) Uani 1 1 d . . . . .
O2 O 0.38143(17) 0.59167(13) 0.69511(8) 0.0163(3) Uani 1 1 d . . . . .
O3 O 0.30750(16) 0.37957(13) 0.64578(8) 0.0166(3) Uani 1 1 d . . . . .
O4 O 0.51118(17) 0.28231(13) 0.50391(8) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.5249 0.2321 0.4761 0.021 Uiso 1 1 d R U . . .
N1 N 0.9092(2) 0.57803(17) 0.60932(10) 0.0187(4) Uani 1 1 d . . . . .
C1 C 0.5563(3) 0.8551(2) 0.60158(12) 0.0230(5) Uani 1 1 d . . . . .
H1 H 0.5961 0.9132 0.5770 0.028 Uiso 1 1 calc R U . . .
C2 C 0.4265(3) 0.8686(2) 0.63372(12) 0.0221(5) Uani 1 1 d . . . . .
H2 H 0.3822 0.9370 0.6324 0.027 Uiso 1 1 calc R U . . .
C3 C 0.3598(2) 0.7850(2) 0.66755(11) 0.0187(5) Uani 1 1 d . . . . .
C4 C 0.4333(2) 0.68837(19) 0.67199(11) 0.0163(5) Uani 1 1 d . . . . .
C5 C 0.4883(2) 0.50944(18) 0.67962(11) 0.0140(4) Uani 1 1 d . . . . .
H5 H 0.5128 0.4692 0.7216 0.017 Uiso 1 1 calc R U . . .
C6 C 0.4375(2) 0.42985(19) 0.62563(11) 0.0141(4) Uani 1 1 d . . . . .
C7 C 0.5606(2) 0.34820(18) 0.61590(11) 0.0130(4) Uani 1 1 d . . . . .
H7 H 0.5865 0.3215 0.6617 0.016 Uiso 1 1 calc R U . . .
C8 C 0.6934(2) 0.40837(18) 0.58761(11) 0.0149(5) Uani 1 1 d . . . . .
H8A H 0.7751 0.3956 0.6175 0.018 Uiso 1 1 calc R U . . .
H8B H 0.7169 0.3801 0.5424 0.018 Uiso 1 1 calc R U . . .
C9 C 0.7911(2) 0.60086(19) 0.56327(12) 0.0167(5) Uani 1 1 d . . . . .
H9 H 0.8214 0.5792 0.5171 0.020 Uiso 1 1 calc R U . . .
C10 C 0.7505(3) 0.7239(2) 0.56058(13) 0.0206(5) Uani 1 1 d . . . . .
H10A H 0.8344 0.7665 0.5735 0.025 Uiso 1 1 calc R U . . .
H10B H 0.7271 0.7426 0.5135 0.025 Uiso 1 1 calc R U . . .
C11 C 0.6281(3) 0.75771(19) 0.60510(12) 0.0182(5) Uani 1 1 d . . . . .
C12 C 0.5666(2) 0.68005(19) 0.64547(11) 0.0155(5) Uani 1 1 d . . . . .
C13 C 0.6199(2) 0.56830(18) 0.65335(11) 0.0144(4) Uani 1 1 d . . . . .
C14 C 0.6639(2) 0.52906(18) 0.58302(11) 0.0141(5) Uani 1 1 d . . . . .
C15 C 0.7434(2) 0.5590(2) 0.70317(12) 0.0172(5) Uani 1 1 d . . . . .
H15A H 0.7154 0.5917 0.7465 0.021 Uiso 1 1 calc R U . . .
H15B H 0.7635 0.4820 0.7114 0.021 Uiso 1 1 calc R U . . .
C16 C 0.8769(2) 0.6135(2) 0.67802(12) 0.0203(5) Uani 1 1 d . . . . .
H16A H 0.8639 0.6924 0.6786 0.024 Uiso 1 1 calc R U . . .
H16B H 0.9566 0.5955 0.7082 0.024 Uiso 1 1 calc R U . . .
C17 C 1.0432(2) 0.6239(2) 0.58638(13) 0.0245(6) Uani 1 1 d . . . . .
H17A H 1.0682 0.5930 0.5426 0.037 Uiso 1 1 calc R U . . .
H17B H 1.1173 0.6073 0.6191 0.037 Uiso 1 1 calc R U . . .
H17C H 1.0336 0.7020 0.5820 0.037 Uiso 1 1 calc R U . . .
C18 C 0.4058(2) 0.49092(18) 0.56077(11) 0.0146(5) Uani 1 1 d . . . . .
H18A H 0.3360 0.5482 0.5699 0.018 Uiso 1 1 calc R U . . .
H18B H 0.3647 0.4412 0.5272 0.018 Uiso 1 1 calc R U . . .
C19 C 0.5423(2) 0.54124(19) 0.53223(11) 0.0155(5) Uani 1 1 d . . . . .
H19A H 0.5677 0.5052 0.4895 0.019 Uiso 1 1 calc R U . . .
H19B H 0.5264 0.6184 0.5227 0.019 Uiso 1 1 calc R U . . .
C20 C 0.5348(2) 0.24697(18) 0.57123(11) 0.0147(5) Uani 1 1 d . . . . .
C21 C 0.4014(3) 0.18568(19) 0.58969(11) 0.0181(5) Uani 1 1 d . . . . .
H21 H 0.3165 0.2309 0.5804 0.022 Uiso 1 1 calc R U . . .
C22 C 0.6654(2) 0.17266(19) 0.57325(11) 0.0166(5) Uani 1 1 d . . . . .
H22A H 0.6437 0.1082 0.5459 0.020 Uiso 1 1 calc R U . . .
H22B H 0.7438 0.2107 0.5505 0.020 Uiso 1 1 calc R U . . .
C23 C 0.7198(3) 0.1341(2) 0.64150(13) 0.0256(6) Uani 1 1 d . . . . .
H23A H 0.7387 0.1971 0.6705 0.031 Uiso 1 1 calc R U . . .
H23B H 0.6462 0.0900 0.6636 0.031 Uiso 1 1 calc R U . . .
C24 C 0.8539(3) 0.0678(2) 0.63458(13) 0.0275(6) Uani 1 1 d . . . . .
H24A H 0.8349 0.0045 0.6068 0.041 Uiso 1 1 calc R U . . .
H24B H 0.8858 0.0449 0.6792 0.041 Uiso 1 1 calc R U . . .
H24C H 0.9274 0.1115 0.6133 0.041 Uiso 1 1 calc R U . . .
C25 C 0.1367(3) 0.8731(2) 0.66988(14) 0.0273(6) Uani 1 1 d . . . . .
H25A H 0.1299 0.8672 0.6208 0.041 Uiso 1 1 calc R U . . .
H25B H 0.1761 0.9434 0.6818 0.041 Uiso 1 1 calc R U . . .
H25C H 0.0426 0.8658 0.6897 0.041 Uiso 1 1 calc R U . . .
C26 C 0.2894(3) 0.3544(2) 0.71565(12) 0.0219(5) Uani 1 1 d . . . . .
H26A H 0.2062 0.3085 0.7212 0.033 Uiso 1 1 calc R U . . .
H26B H 0.2766 0.4209 0.7413 0.033 Uiso 1 1 calc R U . . .
H26C H 0.3731 0.3164 0.7322 0.033 Uiso 1 1 calc R U . . .
O1S O 0.53820(18) 0.13310(14) 0.40502(9) 0.0238(4) Uani 1 1 d . . . . .
H1SB H 0.6268 0.1239 0.3927 0.029 Uiso 1 1 d R U . . .
H1SA H 0.4835 0.0769 0.4010 0.029 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
F1 C21 1.371(3) . ?
F2 C21 1.379(3) . ?
O1 C3 1.380(3) . ?
O1 C25 1.428(3) . ?
O2 C4 1.379(3) . ?
O2 C5 1.473(3) . ?
O3 C6 1.439(3) . ?
O3 C26 1.435(3) . ?
O4 H4 0.8439 . ?
O4 C20 1.427(3) . ?
N1 C9 1.475(3) . ?
N1 C16 1.468(3) . ?
N1 C17 1.465(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.397(4) . ?
C1 C11 1.392(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(4) . ?
C3 C4 1.392(3) . ?
C4 C12 1.373(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.538(3) . ?
C5 C13 1.538(3) . ?
C6 C7 1.560(3) . ?
C6 C18 1.527(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.569(3) . ?
C7 C20 1.561(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.530(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.579(3) . ?
C9 C14 1.551(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.519(3) . ?
C11 C12 1.385(3) . ?
C12 C13 1.488(3) . ?
C13 C14 1.539(3) . ?
C13 C15 1.538(3) . ?
C14 C19 1.541(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.521(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.546(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.522(3) . ?
C20 C22 1.546(3) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.529(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.522(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O1S H1SB 0.8827 . ?
O1S H1SA 0.8747 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C25 116.2(2) . . ?
C4 O2 C5 106.92(17) . . ?
C26 O3 C6 117.85(17) . . ?
C20 O4 H4 111.2 . . ?
C16 N1 C9 111.17(18) . . ?
C17 N1 C9 112.97(19) . . ?
C17 N1 C16 110.72(19) . . ?
C2 C1 H1 119.6 . . ?
C11 C1 H1 119.6 . . ?
C11 C1 C2 120.8(2) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 C1 122.1(2) . . ?
C3 C2 H2 118.9 . . ?
O1 C3 C2 125.0(2) . . ?
O1 C3 C4 118.3(2) . . ?
C2 C3 C4 116.7(2) . . ?
O2 C4 C3 126.6(2) . . ?
C12 C4 O2 113.0(2) . . ?
C12 C4 C3 120.1(2) . . ?
O2 C5 H5 109.5 . . ?
O2 C5 C6 112.18(17) . . ?
O2 C5 C13 107.37(18) . . ?
C6 C5 H5 109.5 . . ?
C6 C5 C13 108.90(17) . . ?
C13 C5 H5 109.5 . . ?
O3 C6 C5 110.74(17) . . ?
O3 C6 C7 113.11(18) . . ?
O3 C6 C18 106.46(17) . . ?
C5 C6 C7 105.73(17) . . ?
C18 C6 C5 109.31(18) . . ?
C18 C6 C7 111.50(18) . . ?
C6 C7 H7 106.7 . . ?
C6 C7 C8 109.54(18) . . ?
C6 C7 C20 118.62(18) . . ?
C8 C7 H7 106.7 . . ?
C20 C7 H7 106.7 . . ?
C20 C7 C8 107.87(17) . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.2 . . ?
C14 C8 C7 110.08(18) . . ?
C14 C8 H8A 109.6 . . ?
C14 C8 H8B 109.6 . . ?
N1 C9 H9 107.5 . . ?
N1 C9 C10 113.13(19) . . ?
N1 C9 C14 108.80(18) . . ?
C10 C9 H9 107.5 . . ?
C14 C9 H9 107.5 . . ?
C14 C9 C10 112.19(18) . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 115.8(2) . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C1 C11 C10 125.8(2) . . ?
C12 C11 C1 115.5(2) . . ?
C12 C11 C10 117.8(2) . . ?
C4 C12 C11 123.9(2) . . ?
C4 C12 C13 110.0(2) . . ?
C11 C12 C13 124.7(2) . . ?
C5 C13 C14 112.18(18) . . ?
C12 C13 C5 101.84(18) . . ?
C12 C13 C14 107.04(18) . . ?
C12 C13 C15 113.39(19) . . ?
C15 C13 C5 111.26(18) . . ?
C15 C13 C14 110.79(18) . . ?
C8 C14 C9 116.02(18) . . ?
C8 C14 C13 107.86(18) . . ?
C8 C14 C19 105.79(18) . . ?
C13 C14 C9 104.96(18) . . ?
C13 C14 C19 111.18(18) . . ?
C19 C14 C9 111.05(18) . . ?
C13 C15 H15A 109.0 . . ?
C13 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C13 112.83(19) . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
N1 C16 C15 110.22(19) . . ?
N1 C16 H16A 109.6 . . ?
N1 C16 H16B 109.6 . . ?
C15 C16 H16A 109.6 . . ?
C15 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C18 H18A 109.6 . . ?
C6 C18 H18B 109.6 . . ?
C6 C18 C19 110.31(17) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
C14 C19 C18 110.27(17) . . ?
C14 C19 H19A 109.6 . . ?
C14 C19 H19B 109.6 . . ?
C18 C19 H19A 109.6 . . ?
C18 C19 H19B 109.6 . . ?
H19A C19 H19B 108.1 . . ?
O4 C20 C7 108.05(18) . . ?
O4 C20 C21 104.50(18) . . ?
O4 C20 C22 109.55(18) . . ?
C21 C20 C7 113.42(18) . . ?
C21 C20 C22 111.09(19) . . ?
C22 C20 C7 110.02(18) . . ?
F1 C21 F2 105.02(18) . . ?
F1 C21 C20 112.03(19) . . ?
F1 C21 H21 110.1 . . ?
F2 C21 C20 109.48(18) . . ?
F2 C21 H21 110.1 . . ?
C20 C21 H21 110.1 . . ?
C20 C22 H22A 107.6 . . ?
C20 C22 H22B 107.6 . . ?
H22A C22 H22B 107.1 . . ?
C23 C22 C20 118.75(19) . . ?
C23 C22 H22A 107.6 . . ?
C23 C22 H22B 107.6 . . ?
C22 C23 H23A 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 C22 111.8(2) . . ?
C24 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
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 . . ?
O1 C25 H25A 109.5 . . ?
O1 C25 H25B 109.5 . . ?
O1 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 . . ?
H1SB O1S H1SA 115.8 . . ?

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
O1 C3 C4 O2 7.4(3) . . . . ?
O1 C3 C4 C12 -179.8(2) . . . . ?
O2 C4 C12 C11 164.0(2) . . . . ?
O2 C4 C12 C13 -3.4(3) . . . . ?
O2 C5 C6 O3 -56.4(2) . . . . ?
O2 C5 C6 C7 -179.27(17) . . . . ?
O2 C5 C6 C18 60.6(2) . . . . ?
O2 C5 C13 C12 -9.1(2) . . . . ?
O2 C5 C13 C14 -123.24(19) . . . . ?
O2 C5 C13 C15 112.01(19) . . . . ?
O3 C6 C7 C8 174.77(17) . . . . ?
O3 C6 C7 C20 50.4(3) . . . . ?
O3 C6 C18 C19 -175.91(18) . . . . ?
O4 C20 C21 F1 -174.86(17) . . . . ?
O4 C20 C21 F2 69.1(2) . . . . ?
O4 C20 C22 C23 173.9(2) . . . . ?
N1 C9 C10 C11 -97.0(2) . . . . ?
N1 C9 C14 C8 -53.5(2) . . . . ?
N1 C9 C14 C13 65.4(2) . . . . ?
N1 C9 C14 C19 -174.33(18) . . . . ?
C1 C2 C3 O1 -173.9(2) . . . . ?
C1 C2 C3 C4 4.3(4) . . . . ?
C1 C11 C12 C4 10.6(3) . . . . ?
C1 C11 C12 C13 176.1(2) . . . . ?
C2 C1 C11 C10 165.1(2) . . . . ?
C2 C1 C11 C12 -4.0(3) . . . . ?
C2 C3 C4 O2 -170.9(2) . . . . ?
C2 C3 C4 C12 1.9(3) . . . . ?
C3 C4 C12 C11 -9.8(4) . . . . ?
C3 C4 C12 C13 -177.2(2) . . . . ?
C4 O2 C5 C6 -112.0(2) . . . . ?
C4 O2 C5 C13 7.6(2) . . . . ?
C4 C12 C13 C5 7.7(2) . . . . ?
C4 C12 C13 C14 125.5(2) . . . . ?
C4 C12 C13 C15 -112.0(2) . . . . ?
C5 O2 C4 C3 170.4(2) . . . . ?
C5 O2 C4 C12 -2.8(2) . . . . ?
C5 C6 C7 C8 -63.9(2) . . . . ?
C5 C6 C7 C20 171.74(18) . . . . ?
C5 C6 C18 C19 64.4(2) . . . . ?
C5 C13 C14 C8 -58.9(2) . . . . ?
C5 C13 C14 C9 176.83(18) . . . . ?
C5 C13 C14 C19 56.7(2) . . . . ?
C5 C13 C15 C16 178.36(19) . . . . ?
C6 C5 C13 C12 112.56(19) . . . . ?
C6 C5 C13 C14 -1.6(3) . . . . ?
C6 C5 C13 C15 -126.3(2) . . . . ?
C6 C7 C8 C14 3.9(2) . . . . ?
C6 C7 C20 O4 65.2(2) . . . . ?
C6 C7 C20 C21 -50.2(3) . . . . ?
C6 C7 C20 C22 -175.27(18) . . . . ?
C6 C18 C19 C14 -8.5(3) . . . . ?
C7 C6 C18 C19 -52.1(2) . . . . ?
C7 C8 C14 C9 173.53(18) . . . . ?
C7 C8 C14 C13 56.2(2) . . . . ?
C7 C8 C14 C19 -62.9(2) . . . . ?
C7 C20 C21 F1 -57.4(3) . . . . ?
C7 C20 C21 F2 -173.51(18) . . . . ?
C7 C20 C22 C23 55.3(3) . . . . ?
C8 C7 C20 O4 -60.0(2) . . . . ?
C8 C7 C20 C21 -175.34(18) . . . . ?
C8 C7 C20 C22 59.6(2) . . . . ?
C8 C14 C19 C18 66.4(2) . . . . ?
C9 N1 C16 C15 57.7(3) . . . . ?
C9 C10 C11 C1 -166.6(2) . . . . ?
C9 C10 C11 C12 2.2(3) . . . . ?
C9 C14 C19 C18 -166.89(18) . . . . ?
C10 C9 C14 C8 -179.44(19) . . . . ?
C10 C9 C14 C13 -60.5(2) . . . . ?
C10 C9 C14 C19 59.7(2) . . . . ?
C10 C11 C12 C4 -159.5(2) . . . . ?
C10 C11 C12 C13 6.1(3) . . . . ?
C11 C1 C2 C3 -3.3(4) . . . . ?
C11 C12 C13 C5 -159.6(2) . . . . ?
C11 C12 C13 C14 -41.7(3) . . . . ?
C11 C12 C13 C15 80.8(3) . . . . ?
C12 C13 C14 C8 -169.79(19) . . . . ?
C12 C13 C14 C9 65.9(2) . . . . ?
C12 C13 C14 C19 -54.2(2) . . . . ?
C12 C13 C15 C16 -67.6(3) . . . . ?
C13 C5 C6 O3 -175.10(17) . . . . ?
C13 C5 C6 C7 62.0(2) . . . . ?
C13 C5 C6 C18 -58.1(2) . . . . ?
C13 C14 C19 C18 -50.4(3) . . . . ?
C13 C15 C16 N1 -50.4(3) . . . . ?
C14 C9 C10 C11 26.5(3) . . . . ?
C14 C13 C15 C16 52.8(3) . . . . ?
C15 C13 C14 C8 66.1(2) . . . . ?
C15 C13 C14 C9 -58.2(2) . . . . ?
C15 C13 C14 C19 -178.31(18) . . . . ?
C16 N1 C9 C10 58.1(3) . . . . ?
C16 N1 C9 C14 -67.3(2) . . . . ?
C17 N1 C9 C10 -67.1(3) . . . . ?
C17 N1 C9 C14 167.55(19) . . . . ?
C17 N1 C16 C15 -175.8(2) . . . . ?
C18 C6 C7 C8 54.8(2) . . . . ?
C18 C6 C7 C20 -69.5(2) . . . . ?
C20 C7 C8 C14 134.30(19) . . . . ?
C20 C22 C23 C24 -176.3(2) . . . . ?
C21 C20 C22 C23 -71.1(3) . . . . ?
C22 C20 C21 F1 67.1(2) . . . . ?
C22 C20 C21 F2 -49.0(2) . . . . ?
C25 O1 C3 C2 19.6(3) . . . . ?
C25 O1 C3 C4 -158.5(2) . . . . ?
C26 O3 C6 C5 -36.7(3) . . . . ?
C26 O3 C6 C7 81.8(2) . . . . ?
C26 O3 C6 C18 -155.41(19) . . . . ?

_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_35
_database_code_depnum_ccdc_archive 'CCDC 2294268'
loop_
_audit_author_name
_audit_author_address
'Anastasia Danshina'
;Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-09-15 deposited with the CCDC.	2023-10-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H31 F2 N O4, C H4 O'
_chemical_formula_sum            'C25 H35 F2 N O5'
_chemical_formula_weight         467.54
_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      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                   7.888(5)
_cell_length_b                   12.342(8)
_cell_length_c                   23.321(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2271(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6475
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.11
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0679 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.8957. The λ/2 correction factor is 0.0015.'
_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    1.368
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            28460
_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         28.999
_diffrn_reflns_theta_min         1.867
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                5269
_reflns_number_total             6037
_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         0.342
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 2082 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   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         6037
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.017
_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)+(0.0554P)²+0.3745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1019
_refine_special_details          ?
_olex2_refinement_description    
;
1. 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
2.a Riding coordinates:
 O4(H4), O1S(H1S)
2.b Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C9(H9), C21(H21)
2.c Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B),
 C19(H19A,H19B)
2.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C1S(H1SA,H1SB,H1SC)
;
_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
F1 F 1.0716(2) 0.49839(14) 0.50371(7) 0.0373(4) Uani 1 1 d . . . . .
F2 F 0.9507(2) 0.65020(13) 0.52717(6) 0.0332(4) Uani 1 1 d . . . . .
O1 O 1.0997(2) 0.40594(15) 0.15352(7) 0.0228(4) Uani 1 1 d . . . . .
O2 O 1.0392(2) 0.37506(13) 0.27289(6) 0.0162(3) Uani 1 1 d . . . . .
O3 O 1.07218(19) 0.52743(13) 0.37205(7) 0.0171(3) Uani 1 1 d . . . . .
O4 O 0.7206(2) 0.49006(14) 0.50835(7) 0.0197(3) Uani 1 1 d . . . . .
H4 H 0.7712 0.4265 0.5160 0.024 Uiso 1 1 d R U . . .
N1 N 0.4635(2) 0.20742(15) 0.34650(8) 0.0150(4) Uani 1 1 d . . . . .
C1 C 0.6404(3) 0.33619(18) 0.16097(10) 0.0170(4) Uani 1 1 d . . . . .
H1 H 0.5439 0.3331 0.1366 0.020 Uiso 1 1 calc R U . . .
C2 C 0.7985(3) 0.36170(19) 0.13759(9) 0.0180(5) Uani 1 1 d . . . . .
H2 H 0.8083 0.3716 0.0973 0.022 Uiso 1 1 calc R U . . .
C3 C 0.9430(3) 0.37312(18) 0.17199(9) 0.0170(4) Uani 1 1 d . . . . .
C4 C 0.9224(3) 0.35336(18) 0.23047(9) 0.0152(4) Uani 1 1 d . . . . .
C5 C 0.9479(3) 0.36737(18) 0.32787(8) 0.0128(4) Uani 1 1 d . . . . .
H5 H 1.0148 0.3209 0.3547 0.015 Uiso 1 1 calc R U . . .
C6 C 0.9152(3) 0.47757(17) 0.35646(9) 0.0127(4) Uani 1 1 d . . . . .
C7 C 0.8248(3) 0.44885(17) 0.41394(9) 0.0130(4) Uani 1 1 d . . . . .
H7 H 0.8958 0.3909 0.4319 0.016 Uiso 1 1 calc R U . . .
C8 C 0.6487(3) 0.39476(18) 0.40207(9) 0.0134(4) Uani 1 1 d . . . . .
H8A H 0.6423 0.3240 0.4219 0.016 Uiso 1 1 calc R U . . .
H8B H 0.5568 0.4416 0.4170 0.016 Uiso 1 1 calc R U . . .
C9 C 0.4661(3) 0.31509(18) 0.31798(9) 0.0134(4) Uani 1 1 d . . . . .
H9 H 0.3649 0.3563 0.3318 0.016 Uiso 1 1 calc R U . . .
C10 C 0.4539(3) 0.3080(2) 0.25092(9) 0.0169(4) Uani 1 1 d . . . . .
H10A H 0.3987 0.2386 0.2406 0.020 Uiso 1 1 calc R U . . .
H10B H 0.3797 0.3672 0.2372 0.020 Uiso 1 1 calc R U . . .
C11 C 0.6216(3) 0.31515(17) 0.21951(9) 0.0155(4) Uani 1 1 d . . . . .
C12 C 0.7697(3) 0.31822(18) 0.25146(9) 0.0135(4) Uani 1 1 d . . . . .
C13 C 0.7774(3) 0.31156(17) 0.31530(9) 0.0118(4) Uani 1 1 d . . . . .
C14 C 0.6261(3) 0.37832(17) 0.33748(9) 0.0120(4) Uani 1 1 d . . . . .
C15 C 0.7741(3) 0.19471(18) 0.33803(9) 0.0149(4) Uani 1 1 d . . . . .
H15A H 0.8658 0.1527 0.3195 0.018 Uiso 1 1 calc R U . . .
H15B H 0.7961 0.1954 0.3798 0.018 Uiso 1 1 calc R U . . .
C16 C 0.6059(3) 0.13946(18) 0.32675(10) 0.0173(4) Uani 1 1 d . . . . .
H16A H 0.5938 0.1253 0.2852 0.021 Uiso 1 1 calc R U . . .
H16B H 0.6029 0.0690 0.3470 0.021 Uiso 1 1 calc R U . . .
C17 C 0.3031(3) 0.14951(19) 0.33799(11) 0.0202(5) Uani 1 1 d . . . . .
H17A H 0.2090 0.1945 0.3516 0.030 Uiso 1 1 calc R U . . .
H17B H 0.3054 0.0813 0.3595 0.030 Uiso 1 1 calc R U . . .
H17C H 0.2878 0.1340 0.2971 0.030 Uiso 1 1 calc R U . . .
C18 C 0.8050(3) 0.54583(18) 0.31664(9) 0.0146(4) Uani 1 1 d . . . . .
H18A H 0.8583 0.5503 0.2783 0.018 Uiso 1 1 calc R U . . .
H18B H 0.7944 0.6202 0.3321 0.018 Uiso 1 1 calc R U . . .
C19 C 0.6271(3) 0.49352(17) 0.31153(9) 0.0141(4) Uani 1 1 d . . . . .
H19A H 0.5431 0.5391 0.3318 0.017 Uiso 1 1 calc R U . . .
H19B H 0.5940 0.4898 0.2706 0.017 Uiso 1 1 calc R U . . .
C20 C 0.8054(3) 0.53814(18) 0.46086(9) 0.0159(4) Uani 1 1 d . . . . .
C21 C 0.9766(3) 0.5810(2) 0.48200(10) 0.0236(5) Uani 1 1 d . . . . .
H21 H 1.0385 0.6185 0.4503 0.028 Uiso 1 1 calc R U . . .
C22 C 1.1138(3) 0.4313(2) 0.09403(10) 0.0260(5) Uani 1 1 d . . . . .
H22A H 1.0861 0.3670 0.0712 0.039 Uiso 1 1 calc R U . . .
H22B H 1.2299 0.4544 0.0855 0.039 Uiso 1 1 calc R U . . .
H22C H 1.0349 0.4900 0.0845 0.039 Uiso 1 1 calc R U . . .
C23 C 1.1677(3) 0.57925(19) 0.32795(10) 0.0196(5) Uani 1 1 d . . . . .
H23A H 1.2052 0.5251 0.3000 0.029 Uiso 1 1 calc R U . . .
H23B H 1.2669 0.6149 0.3448 0.029 Uiso 1 1 calc R U . . .
H23C H 1.0967 0.6334 0.3087 0.029 Uiso 1 1 calc R U . . .
C24 C 0.6990(3) 0.6362(2) 0.44403(11) 0.0250(5) Uani 1 1 d . . . . .
H24A H 0.5917 0.6117 0.4273 0.038 Uiso 1 1 calc R U . . .
H24B H 0.7610 0.6798 0.4159 0.038 Uiso 1 1 calc R U . . .
H24C H 0.6758 0.6802 0.4781 0.038 Uiso 1 1 calc R U . . .
O1S O 0.8709(2) 0.29310(14) 0.53578(8) 0.0266(4) Uani 1 1 d . . . . .
H1S H 0.9189 0.2889 0.5689 0.032 Uiso 1 1 d R U . . .
C1S C 0.7826(4) 0.1953(2) 0.52560(12) 0.0313(6) Uani 1 1 d . . . . .
H1SA H 0.6745 0.2111 0.5066 0.047 Uiso 1 1 calc R U . . .
H1SB H 0.7609 0.1587 0.5622 0.047 Uiso 1 1 calc R U . . .
H1SC H 0.8511 0.1482 0.5009 0.047 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 1.363(3) . ?
F2 C21 1.372(3) . ?
O1 C3 1.370(3) . ?
O1 C22 1.427(3) . ?
O2 C4 1.378(3) . ?
O2 C5 1.474(3) . ?
O3 C6 1.429(3) . ?
O3 C23 1.426(3) . ?
O4 H4 0.8983 . ?
O4 C20 1.423(3) . ?
N1 C9 1.486(3) . ?
N1 C16 1.475(3) . ?
N1 C17 1.466(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.397(3) . ?
C1 C11 1.398(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(3) . ?
C3 C4 1.395(3) . ?
C4 C12 1.370(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.536(3) . ?
C5 C13 1.539(3) . ?
C6 C7 1.560(3) . ?
C6 C18 1.526(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.566(3) . ?
C7 C20 1.560(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C14 1.530(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.569(3) . ?
C9 C14 1.552(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.515(3) . ?
C11 C12 1.387(3) . ?
C12 C13 1.492(3) . ?
C13 C14 1.540(3) . ?
C13 C15 1.537(3) . ?
C14 C19 1.545(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.515(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.549(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.531(3) . ?
C20 C24 1.524(3) . ?
C21 H21 1.0000 . ?
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 . ?
O1S H1S 0.8625 . ?
O1S C1S 1.414(3) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 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
C3 O1 C22 116.16(19) . . ?
C4 O2 C5 106.59(17) . . ?
C23 O3 C6 117.85(17) . . ?
C20 O4 H4 108.1 . . ?
C16 N1 C9 110.98(17) . . ?
C17 N1 C9 112.79(17) . . ?
C17 N1 C16 109.70(17) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C11 121.2(2) . . ?
C11 C1 H1 119.4 . . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.7(2) . . ?
C3 C2 H2 119.2 . . ?
O1 C3 C2 125.7(2) . . ?
O1 C3 C4 117.6(2) . . ?
C4 C3 C2 116.6(2) . . ?
O2 C4 C3 126.2(2) . . ?
C12 C4 O2 113.10(19) . . ?
C12 C4 C3 120.5(2) . . ?
O2 C5 H5 108.9 . . ?
O2 C5 C6 113.72(17) . . ?
O2 C5 C13 106.87(16) . . ?
C6 C5 H5 108.9 . . ?
C6 C5 C13 109.42(17) . . ?
C13 C5 H5 108.9 . . ?
O3 C6 C5 110.27(17) . . ?
O3 C6 C7 105.99(16) . . ?
O3 C6 C18 114.25(18) . . ?
C5 C6 C7 104.38(17) . . ?
C18 C6 C5 108.67(17) . . ?
C18 C6 C7 112.82(18) . . ?
C6 C7 H7 105.4 . . ?
C6 C7 C8 110.53(17) . . ?
C6 C7 C20 119.15(18) . . ?
C8 C7 H7 105.4 . . ?
C20 C7 H7 105.4 . . ?
C20 C7 C8 109.77(17) . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C14 C8 C7 109.52(17) . . ?
C14 C8 H8A 109.8 . . ?
C14 C8 H8B 109.8 . . ?
N1 C9 H9 107.4 . . ?
N1 C9 C10 113.28(18) . . ?
N1 C9 C14 109.27(17) . . ?
C10 C9 H9 107.4 . . ?
C14 C9 H9 107.4 . . ?
C14 C9 C10 111.73(17) . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 115.15(17) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C1 C11 C10 125.17(19) . . ?
C12 C11 C1 115.5(2) . . ?
C12 C11 C10 118.54(19) . . ?
C4 C12 C11 123.9(2) . . ?
C4 C12 C13 109.78(19) . . ?
C11 C12 C13 124.65(19) . . ?
C5 C13 C14 111.95(17) . . ?
C12 C13 C5 101.57(17) . . ?
C12 C13 C14 105.92(17) . . ?
C12 C13 C15 113.28(18) . . ?
C15 C13 C5 111.65(17) . . ?
C15 C13 C14 111.93(17) . . ?
C8 C14 C9 116.74(17) . . ?
C8 C14 C13 108.13(17) . . ?
C8 C14 C19 105.24(17) . . ?
C13 C14 C9 105.23(17) . . ?
C13 C14 C19 110.90(17) . . ?
C19 C14 C9 110.63(17) . . ?
C13 C15 H15A 109.2 . . ?
C13 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C13 112.15(18) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
N1 C16 C15 110.90(18) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C18 H18A 109.8 . . ?
C6 C18 H18B 109.8 . . ?
C6 C18 C19 109.44(17) . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 H18A 109.8 . . ?
C19 C18 H18B 109.8 . . ?
C14 C19 C18 110.99(17) . . ?
C14 C19 H19A 109.4 . . ?
C14 C19 H19B 109.4 . . ?
C18 C19 H19A 109.4 . . ?
C18 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
O4 C20 C7 107.29(18) . . ?
O4 C20 C21 107.91(19) . . ?
O4 C20 C24 105.82(19) . . ?
C21 C20 C7 112.53(18) . . ?
C24 C20 C7 115.73(19) . . ?
C24 C20 C21 107.1(2) . . ?
F1 C21 F2 105.2(2) . . ?
F1 C21 C20 110.3(2) . . ?
F1 C21 H21 110.6 . . ?
F2 C21 C20 109.4(2) . . ?
F2 C21 H21 110.6 . . ?
C20 C21 H21 110.6 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C24 H24A 109.5 . . ?
C20 C24 H24B 109.5 . . ?
C20 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C1S O1S H1S 108.4 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 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 C3 C4 O2 7.8(3) . . . . ?
O1 C3 C4 C12 -178.7(2) . . . . ?
O2 C4 C12 C11 164.5(2) . . . . ?
O2 C4 C12 C13 -1.3(3) . . . . ?
O2 C5 C6 O3 -64.5(2) . . . . ?
O2 C5 C6 C7 -177.99(16) . . . . ?
O2 C5 C6 C18 61.4(2) . . . . ?
O2 C5 C13 C12 -13.9(2) . . . . ?
O2 C5 C13 C14 -126.51(18) . . . . ?
O2 C5 C13 C15 107.11(19) . . . . ?
O3 C6 C7 C8 179.21(16) . . . . ?
O3 C6 C7 C20 50.7(2) . . . . ?
O3 C6 C18 C19 -169.98(16) . . . . ?
O4 C20 C21 F1 59.8(2) . . . . ?
O4 C20 C21 F2 -55.4(3) . . . . ?
N1 C9 C10 C11 -97.8(2) . . . . ?
N1 C9 C14 C8 -56.2(2) . . . . ?
N1 C9 C14 C13 63.7(2) . . . . ?
N1 C9 C14 C19 -176.50(17) . . . . ?
C1 C2 C3 O1 -174.7(2) . . . . ?
C1 C2 C3 C4 2.6(3) . . . . ?
C1 C11 C12 C4 8.6(3) . . . . ?
C1 C11 C12 C13 172.3(2) . . . . ?
C2 C1 C11 C10 167.7(2) . . . . ?
C2 C1 C11 C12 -1.9(3) . . . . ?
C2 C3 C4 O2 -169.7(2) . . . . ?
C2 C3 C4 C12 3.8(3) . . . . ?
C3 C4 C12 C11 -9.9(3) . . . . ?
C3 C4 C12 C13 -175.6(2) . . . . ?
C4 O2 C5 C6 -107.02(19) . . . . ?
C4 O2 C5 C13 13.8(2) . . . . ?
C4 C12 C13 C5 9.5(2) . . . . ?
C4 C12 C13 C14 126.55(19) . . . . ?
C4 C12 C13 C15 -110.4(2) . . . . ?
C5 O2 C4 C3 165.9(2) . . . . ?
C5 O2 C4 C12 -8.1(2) . . . . ?
C5 C6 C7 C8 -64.3(2) . . . . ?
C5 C6 C7 C20 167.17(18) . . . . ?
C5 C6 C18 C19 66.4(2) . . . . ?
C5 C13 C14 C8 -58.2(2) . . . . ?
C5 C13 C14 C9 176.40(16) . . . . ?
C5 C13 C14 C19 56.7(2) . . . . ?
C5 C13 C15 C16 179.09(17) . . . . ?
C6 C5 C13 C12 109.65(18) . . . . ?
C6 C5 C13 C14 -3.0(2) . . . . ?
C6 C5 C13 C15 -129.34(18) . . . . ?
C6 C7 C8 C14 4.6(2) . . . . ?
C6 C7 C20 O4 -179.49(18) . . . . ?
C6 C7 C20 C21 -61.0(3) . . . . ?
C6 C7 C20 C24 62.7(3) . . . . ?
C6 C18 C19 C14 -11.6(2) . . . . ?
C7 C6 C18 C19 -48.8(2) . . . . ?
C7 C8 C14 C9 174.09(17) . . . . ?
C7 C8 C14 C13 55.8(2) . . . . ?
C7 C8 C14 C19 -62.8(2) . . . . ?
C7 C20 C21 F1 -58.4(2) . . . . ?
C7 C20 C21 F2 -173.60(19) . . . . ?
C8 C7 C20 O4 51.7(2) . . . . ?
C8 C7 C20 C21 170.20(19) . . . . ?
C8 C7 C20 C24 -66.2(2) . . . . ?
C8 C14 C19 C18 68.5(2) . . . . ?
C9 N1 C16 C15 57.8(2) . . . . ?
C9 C10 C11 C1 -164.1(2) . . . . ?
C9 C10 C11 C12 5.2(3) . . . . ?
C9 C14 C19 C18 -164.61(17) . . . . ?
C10 C9 C14 C8 177.64(18) . . . . ?
C10 C9 C14 C13 -62.5(2) . . . . ?
C10 C9 C14 C19 57.4(2) . . . . ?
C10 C11 C12 C4 -161.7(2) . . . . ?
C10 C11 C12 C13 2.0(3) . . . . ?
C11 C1 C2 C3 -3.5(3) . . . . ?
C11 C12 C13 C5 -156.1(2) . . . . ?
C11 C12 C13 C14 -39.1(3) . . . . ?
C11 C12 C13 C15 84.0(3) . . . . ?
C12 C13 C14 C8 -168.03(17) . . . . ?
C12 C13 C14 C9 66.5(2) . . . . ?
C12 C13 C14 C19 -53.1(2) . . . . ?
C12 C13 C15 C16 -67.0(2) . . . . ?
C13 C5 C6 O3 176.05(16) . . . . ?
C13 C5 C6 C7 62.6(2) . . . . ?
C13 C5 C6 C18 -58.0(2) . . . . ?
C13 C14 C19 C18 -48.2(2) . . . . ?
C13 C15 C16 N1 -50.7(2) . . . . ?
C14 C9 C10 C11 26.1(3) . . . . ?
C14 C13 C15 C16 52.7(2) . . . . ?
C15 C13 C14 C8 68.1(2) . . . . ?
C15 C13 C14 C9 -57.4(2) . . . . ?
C15 C13 C14 C19 -177.03(17) . . . . ?
C16 N1 C9 C10 59.3(2) . . . . ?
C16 N1 C9 C14 -65.9(2) . . . . ?
C17 N1 C9 C10 -64.2(2) . . . . ?
C17 N1 C9 C14 170.52(17) . . . . ?
C17 N1 C16 C15 -176.88(18) . . . . ?
C18 C6 C7 C8 53.5(2) . . . . ?
C18 C6 C7 C20 -75.0(2) . . . . ?
C20 C7 C8 C14 138.02(18) . . . . ?
C22 O1 C3 C2 0.7(3) . . . . ?
C22 O1 C3 C4 -176.6(2) . . . . ?
C23 O3 C6 C5 78.4(2) . . . . ?
C23 O3 C6 C7 -169.15(18) . . . . ?
C23 O3 C6 C18 -44.3(2) . . . . ?
C24 C20 C21 F1 173.34(19) . . . . ?
C24 C20 C21 F2 58.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
