# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_LA122
_database_code_depnum_ccdc_archive 'CCDC 2209064'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-09-23 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H27 N O5'
_chemical_formula_sum            'C20 H27 N O5'
_chemical_formula_weight         361.42

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   13.0105(3)
_cell_length_b                   15.4617(4)
_cell_length_c                   19.8646(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3996.05(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9864
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      30.86
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             1552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8062
_exptl_absorpt_correction_T_max  0.8750
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-Ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            83405
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.288
_diffrn_reflns_theta_max         30.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6103
_reflns_number_gt                4766
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2018)'
_computing_cell_refinement       'SAINT (Bruker, 2018)'
_computing_data_reduction        'SAINT (Bruker, 2018)'
_computing_structure_solution    
;
SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)
;
_computing_structure_refinement  
;
SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)
;
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_computing_publication_material  
;
SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)
;
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0482P)²+2.0398P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6103
_refine_ls_number_parameters     243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.50784(7) 0.52761(6) 0.78022(5) 0.0241(2) Uani 1 1 d . . . . .
O2 O 0.66869(7) 0.46273(6) 0.71086(4) 0.02048(18) Uani 1 1 d . . . . .
O3 O 0.73138(8) 0.41458(7) 0.56032(5) 0.0353(2) Uani 1 1 d . . . . .
O4 O 0.65895(7) 0.61022(7) 0.51424(5) 0.0275(2) Uani 1 1 d . . . . .
O5 O 0.92123(7) 0.64884(7) 0.90713(5) 0.0298(2) Uani 1 1 d . . . . .
N1 N 0.67417(8) 0.54467(7) 0.68044(5) 0.0190(2) Uani 1 1 d . . . . .
C1 C 0.59047(9) 0.53044(8) 0.80903(6) 0.0179(2) Uani 1 1 d . . . . .
C2 C 0.67905(9) 0.47257(8) 0.78282(6) 0.0183(2) Uani 1 1 d . . . . .
C3 C 0.78247(9) 0.50914(8) 0.79861(6) 0.0203(2) Uani 1 1 d . . . . .
H3 H 0.840431 0.491129 0.773124 0.024 Uiso 1 1 calc R U . . .
C4 C 0.79478(9) 0.56697(8) 0.84819(6) 0.0192(2) Uani 1 1 d . . . . .
C5 C 0.70770(9) 0.60124(8) 0.88643(6) 0.0180(2) Uani 1 1 d . . . . .
H5 H 0.721110 0.635546 0.925117 0.022 Uiso 1 1 calc R U . . .
C6 C 0.60917(8) 0.58607(7) 0.86894(6) 0.0166(2) Uani 1 1 d . . . . .
C7 C 0.54847(11) 0.41847(9) 0.57156(7) 0.0285(3) Uani 1 1 d . . . . .
H7A H 0.505511 0.463918 0.551784 0.043 Uiso 1 1 calc R U . . .
H7B H 0.520595 0.401956 0.615555 0.043 Uiso 1 1 calc R U . . .
H7C H 0.548991 0.367956 0.541772 0.043 Uiso 1 1 calc R U . . .
C8 C 0.65547(10) 0.45134(8) 0.58005(6) 0.0214(2) Uani 1 1 d . . . . .
C9 C 0.66651(8) 0.53738(8) 0.61640(6) 0.0177(2) Uani 1 1 d . . . . .
C10 C 0.66680(8) 0.61830(8) 0.57486(6) 0.0207(2) Uani 1 1 d . . . . .
C11 C 0.67432(10) 0.70370(9) 0.60973(7) 0.0271(3) Uani 1 1 d . . . . .
H11A H 0.719539 0.698352 0.648959 0.041 Uiso 1 1 calc R U . . .
H11B H 0.605776 0.721956 0.624446 0.041 Uiso 1 1 calc R U . . .
H11C H 0.702559 0.746793 0.578639 0.041 Uiso 1 1 calc R U . . .
C12 C 0.66698(10) 0.37776(8) 0.81129(6) 0.0235(3) Uani 1 1 d . . . . .
C13 C 0.56391(13) 0.33939(10) 0.78851(8) 0.0374(4) Uani 1 1 d . . . . .
H13A H 0.559514 0.341340 0.739280 0.056 Uiso 1 1 calc R U . . .
H13B H 0.507439 0.373075 0.807958 0.056 Uiso 1 1 calc R U . . .
H13C H 0.558953 0.279244 0.803732 0.056 Uiso 1 1 calc R U . . .
C14 C 0.75468(15) 0.32203(10) 0.78413(9) 0.0448(4) Uani 1 1 d . . . . .
H14A H 0.756578 0.326263 0.734921 0.067 Uiso 1 1 calc R U . . .
H14B H 0.743615 0.261654 0.797284 0.067 Uiso 1 1 calc R U . . .
H14C H 0.820070 0.342428 0.802763 0.067 Uiso 1 1 calc R U . . .
C15 C 0.66998(12) 0.37749(9) 0.88825(7) 0.0305(3) Uani 1 1 d . . . . .
H15A H 0.610668 0.409442 0.905759 0.046 Uiso 1 1 calc R U . . .
H15B H 0.733525 0.405133 0.903699 0.046 Uiso 1 1 calc R U . . .
H15C H 0.667656 0.317729 0.904613 0.046 Uiso 1 1 calc R U . . .
C16 C 0.89972(9) 0.59778(9) 0.86294(6) 0.0234(3) Uani 1 1 d . . . . .
H16 H 0.954241 0.576122 0.835958 0.028 Uiso 1 1 calc R U . . .
C17 C 0.51744(9) 0.62858(8) 0.90389(6) 0.0190(2) Uani 1 1 d . . . . .
C18 C 0.43575(9) 0.56048(9) 0.92188(7) 0.0253(3) Uani 1 1 d . . . . .
H18A H 0.405174 0.537538 0.880481 0.038 Uiso 1 1 calc R U . . .
H18B H 0.382060 0.587255 0.949500 0.038 Uiso 1 1 calc R U . . .
H18C H 0.467979 0.513251 0.947121 0.038 Uiso 1 1 calc R U . . .
C19 C 0.55104(10) 0.67467(9) 0.96852(7) 0.0245(3) Uani 1 1 d . . . . .
H19A H 0.598037 0.722019 0.957201 0.037 Uiso 1 1 calc R U . . .
H19B H 0.586089 0.633441 0.998135 0.037 Uiso 1 1 calc R U . . .
H19C H 0.490495 0.698024 0.991557 0.037 Uiso 1 1 calc R U . . .
C20 C 0.47041(10) 0.69632(9) 0.85607(7) 0.0268(3) Uani 1 1 d . . . . .
H20A H 0.443352 0.667338 0.815941 0.040 Uiso 1 1 calc R U . . .
H20B H 0.523454 0.737937 0.842740 0.040 Uiso 1 1 calc R U . . .
H20C H 0.414514 0.726786 0.879126 0.040 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2186(14) . ?
O2 N1 1.4054(13) . ?
O2 C2 1.4438(13) . ?
O3 C8 1.2050(16) . ?
O4 C10 1.2150(16) . ?
O5 C16 1.2134(16) . ?
N1 C9 1.2809(15) . ?
C1 C6 1.4884(16) . ?
C1 C2 1.5492(17) . ?
C2 C3 1.4928(17) . ?
C2 C12 1.5791(17) . ?
C3 C4 1.3400(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.4632(16) . ?
C4 C16 1.4754(16) . ?
C5 C6 1.3487(15) . ?
C5 H5 0.9500 . ?
C6 C17 1.5293(16) . ?
C7 C8 1.4916(18) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.5204(17) . ?
C9 C10 1.4988(17) . ?
C10 C11 1.4942(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C14 1.528(2) . ?
C12 C15 1.5293(18) . ?
C12 C13 1.535(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 0.9500 . ?
C17 C19 1.5319(17) . ?
C17 C18 1.5382(17) . ?
C17 C20 1.5407(17) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
N1 O2 C2 109.02(9) . . ?
C9 N1 O2 110.10(10) . . ?
O1 C1 C6 122.71(11) . . ?
O1 C1 C2 118.53(11) . . ?
C6 C1 C2 118.75(9) . . ?
O2 C2 C3 109.40(10) . . ?
O2 C2 C1 108.92(9) . . ?
C3 C2 C1 112.40(10) . . ?
O2 C2 C12 104.33(9) . . ?
C3 C2 C12 111.47(10) . . ?
C1 C2 C12 109.98(10) . . ?
C4 C3 C2 121.00(11) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 122.05(11) . . ?
C3 C4 C16 118.16(11) . . ?
C5 C4 C16 119.78(11) . . ?
C6 C5 C4 122.64(11) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C1 117.50(10) . . ?
C5 C6 C17 123.38(11) . . ?
C1 C6 C17 118.93(10) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C8 C7 124.57(12) . . ?
O3 C8 C9 119.32(12) . . ?
C7 C8 C9 116.10(11) . . ?
N1 C9 C10 118.23(11) . . ?
N1 C9 C8 123.78(11) . . ?
C10 C9 C8 117.98(10) . . ?
O4 C10 C11 123.76(12) . . ?
O4 C10 C9 117.37(12) . . ?
C11 C10 C9 118.86(11) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C15 109.41(12) . . ?
C14 C12 C13 109.29(13) . . ?
C15 C12 C13 108.42(12) . . ?
C14 C12 C2 108.83(11) . . ?
C15 C12 C2 110.98(10) . . ?
C13 C12 C2 109.89(10) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O5 C16 C4 124.55(12) . . ?
O5 C16 H16 117.7 . . ?
C4 C16 H16 117.7 . . ?
C6 C17 C19 110.95(9) . . ?
C6 C17 C18 110.51(10) . . ?
C19 C17 C18 108.72(10) . . ?
C6 C17 C20 108.80(10) . . ?
C19 C17 C20 108.29(10) . . ?
C18 C17 C20 109.53(10) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C2 O2 N1 C9 179.14(9) . . . . ?
N1 O2 C2 C3 -62.98(12) . . . . ?
N1 O2 C2 C1 60.23(11) . . . . ?
N1 O2 C2 C12 177.65(9) . . . . ?
O1 C1 C2 O2 31.85(15) . . . . ?
C6 C1 C2 O2 -149.12(10) . . . . ?
O1 C1 C2 C3 153.26(11) . . . . ?
C6 C1 C2 C3 -27.72(14) . . . . ?
O1 C1 C2 C12 -81.92(13) . . . . ?
C6 C1 C2 C12 97.11(12) . . . . ?
O2 C2 C3 C4 142.12(11) . . . . ?
C1 C2 C3 C4 20.99(16) . . . . ?
C12 C2 C3 C4 -103.02(13) . . . . ?
C2 C3 C4 C5 -3.87(18) . . . . ?
C2 C3 C4 C16 177.54(11) . . . . ?
C3 C4 C5 C6 -8.93(19) . . . . ?
C16 C4 C5 C6 169.65(11) . . . . ?
C4 C5 C6 C1 1.38(17) . . . . ?
C4 C5 C6 C17 -173.63(11) . . . . ?
O1 C1 C6 C5 -163.64(12) . . . . ?
C2 C1 C6 C5 17.37(16) . . . . ?
O1 C1 C6 C17 11.60(17) . . . . ?
C2 C1 C6 C17 -167.39(10) . . . . ?
O2 N1 C9 C10 177.82(9) . . . . ?
O2 N1 C9 C8 -1.20(15) . . . . ?
O3 C8 C9 N1 -92.25(16) . . . . ?
C7 C8 C9 N1 87.72(15) . . . . ?
O3 C8 C9 C10 88.73(14) . . . . ?
C7 C8 C9 C10 -91.31(13) . . . . ?
N1 C9 C10 O4 -179.64(11) . . . . ?
C8 C9 C10 O4 -0.56(16) . . . . ?
N1 C9 C10 C11 -0.94(16) . . . . ?
C8 C9 C10 C11 178.14(11) . . . . ?
O2 C2 C12 C14 62.80(13) . . . . ?
C3 C2 C12 C14 -55.16(14) . . . . ?
C1 C2 C12 C14 179.48(12) . . . . ?
O2 C2 C12 C15 -176.74(10) . . . . ?
C3 C2 C12 C15 65.30(14) . . . . ?
C1 C2 C12 C15 -60.06(13) . . . . ?
O2 C2 C12 C13 -56.83(13) . . . . ?
C3 C2 C12 C13 -174.79(11) . . . . ?
C1 C2 C12 C13 59.85(13) . . . . ?
C3 C4 C16 O5 -178.75(13) . . . . ?
C5 C4 C16 O5 2.6(2) . . . . ?
C5 C6 C17 C19 -11.30(16) . . . . ?
C1 C6 C17 C19 173.76(10) . . . . ?
C5 C6 C17 C18 -131.98(12) . . . . ?
C1 C6 C17 C18 53.08(14) . . . . ?
C5 C6 C17 C20 107.73(13) . . . . ?
C1 C6 C17 C20 -67.21(13) . . . . ?

_refine_diff_density_max         0.383
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_B674
_database_code_depnum_ccdc_archive 'CCDC 2209065'
loop_
_audit_author_name
_audit_author_address
'Mikhail Euguenievich Minyaev'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-09-23 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N O3'
_chemical_formula_sum            'C24 H21 N O3'
_chemical_formula_weight         371.42

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.4081(3)
_cell_length_b                   29.0616(9)
_cell_length_c                   8.9737(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.5260(9)
_cell_angle_gamma                90
_cell_volume                     1978.71(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9151
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      38.58

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.57
_exptl_crystal_size_min          0.48
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7773
_exptl_absorpt_correction_T_max  0.8026
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-Ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            82890
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.611
_diffrn_reflns_theta_max         37.790
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10629
_reflns_number_gt                8851
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    
'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement  
'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0611P)²+0.5428P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10629
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.68321(6) 0.34499(2) 0.34870(6) 0.01555(9) Uani 1 1 d . . . . .
O2 O 0.52281(12) 0.28442(3) 0.57121(9) 0.03643(16) Uani 1 1 d . . . . .
O3 O 0.25082(11) 0.23890(3) 0.23270(11) 0.03635(16) Uani 1 1 d . . . . .
N1 N 0.51406(8) 0.33097(2) 0.23836(7) 0.01612(10) Uani 1 1 d . . . . .
C1 C 0.73055(14) 0.24715(3) 0.49483(13) 0.03215(18) Uani 1 1 d . . . . .
H1A H 0.702566 0.225793 0.402403 0.048 Uiso 1 1 calc R U . . .
H1B H 0.765235 0.229680 0.597523 0.048 Uiso 1 1 calc R U . . .
H1C H 0.827792 0.267252 0.503616 0.048 Uiso 1 1 calc R U . . .
C2 C 0.57236(11) 0.27566(3) 0.46585(9) 0.02253(13) Uani 1 1 d . . . . .
C3 C 0.46688(9) 0.29566(2) 0.29502(9) 0.01754(11) Uani 1 1 d . . . . .
C4 C 0.29051(11) 0.27500(3) 0.18855(10) 0.02277(13) Uani 1 1 d . . . . .
C5 C 0.17238(12) 0.29975(4) 0.03492(12) 0.03126(17) Uani 1 1 d . . . . .
H5A H 0.243305 0.313971 -0.015249 0.047 Uiso 0.45(4) 1 calc R U P A 1
H5B H 0.106991 0.323663 0.062131 0.047 Uiso 0.45(4) 1 calc R U P A 1
H5C H 0.089232 0.277895 -0.043062 0.047 Uiso 0.45(4) 1 calc R U P A 1
H5D H 0.173724 0.332740 0.058126 0.047 Uiso 0.55(4) 1 calc R U P A 2
H5E H 0.051967 0.287947 -0.003765 0.047 Uiso 0.55(4) 1 calc R U P A 2
H5F H 0.213836 0.294843 -0.050541 0.047 Uiso 0.55(4) 1 calc R U P A 2
C6 C 0.72581(8) 0.39154(2) 0.31176(7) 0.01223(9) Uani 1 1 d . . . . .
C7 C 0.57752(8) 0.42406(2) 0.29736(7) 0.01282(9) Uani 1 1 d . . . . .
C8 C 0.49644(9) 0.41841(2) 0.40362(8) 0.01626(10) Uani 1 1 d . . . . .
H8 H 0.530947 0.393663 0.480264 0.020 Uiso 1 1 calc R U . . .
C9 C 0.36601(9) 0.44866(3) 0.39799(9) 0.01883(11) Uani 1 1 d . . . . .
H9 H 0.311477 0.444401 0.470268 0.023 Uiso 1 1 calc R U . . .
C10 C 0.31501(9) 0.48515(3) 0.28685(9) 0.01968(12) Uani 1 1 d . . . . .
H10 H 0.224898 0.505620 0.282209 0.024 Uiso 1 1 calc R U . . .
C11 C 0.39626(10) 0.49150(3) 0.18299(9) 0.01956(12) Uani 1 1 d . . . . .
H11 H 0.362967 0.516660 0.108090 0.023 Uiso 1 1 calc R U . . .
C12 C 0.52704(9) 0.46103(2) 0.18797(8) 0.01575(10) Uani 1 1 d . . . . .
H12 H 0.581947 0.465580 0.116140 0.019 Uiso 1 1 calc R U . . .
C13 C 0.76057(8) 0.39133(2) 0.15733(7) 0.01273(9) Uani 1 1 d . . . . .
C14 C 0.91446(9) 0.41052(3) 0.16112(8) 0.01884(11) Uani 1 1 d . . . . .
H14 H 0.999574 0.423257 0.261250 0.023 Uiso 1 1 calc R U . . .
C15 C 0.94547(10) 0.41130(3) 0.02027(9) 0.02203(13) Uani 1 1 d . . . . .
H15 H 1.050609 0.424727 0.025118 0.026 Uiso 1 1 calc R U . . .
C16 C 0.82314(10) 0.39254(3) -0.12682(9) 0.01932(12) Uani 1 1 d . . . . .
H16 H 0.844918 0.392456 -0.222276 0.023 Uiso 1 1 calc R U . . .
C17 C 0.66856(10) 0.37389(3) -0.13257(8) 0.01939(12) Uani 1 1 d . . . . .
H17 H 0.583827 0.361179 -0.232969 0.023 Uiso 1 1 calc R U . . .
C18 C 0.63636(9) 0.37361(2) 0.00721(8) 0.01660(11) Uani 1 1 d . . . . .
H18 H 0.528905 0.361248 0.000575 0.020 Uiso 1 1 calc R U . . .
C19 C 0.89477(8) 0.40155(2) 0.46741(7) 0.01300(9) Uani 1 1 d . . . . .
C20 C 0.92737(8) 0.44478(2) 0.54145(8) 0.01442(10) Uani 1 1 d . . . . .
H20 H 0.843223 0.468689 0.495312 0.017 Uiso 1 1 calc R U . . .
C21 C 1.08266(9) 0.45329(2) 0.68290(8) 0.01752(11) Uani 1 1 d . . . . .
H21 H 1.103569 0.482917 0.732458 0.021 Uiso 1 1 calc R U . . .
C22 C 1.20664(9) 0.41862(3) 0.75141(9) 0.01975(12) Uani 1 1 d . . . . .
H22 H 1.311628 0.424315 0.848458 0.024 Uiso 1 1 calc R U . . .
C23 C 1.17609(9) 0.37545(3) 0.67693(9) 0.02053(12) Uani 1 1 d . . . . .
H23 H 1.260917 0.351677 0.722853 0.025 Uiso 1 1 calc R U . . .
C24 C 1.02185(9) 0.36702(2) 0.53558(9) 0.01781(11) Uani 1 1 d . . . . .
H24 H 1.002545 0.337567 0.484823 0.021 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.3984(7) . ?
O1 C6 1.4735(8) . ?
O2 C2 1.2132(11) . ?
O3 C4 1.2177(10) . ?
N1 C3 1.2818(9) . ?
C1 C2 1.4916(13) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.5175(11) . ?
C3 C4 1.5004(10) . ?
C4 C5 1.4916(13) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5 H5D 0.9800 . ?
C5 H5E 0.9800 . ?
C5 H5F 0.9800 . ?
C6 C7 1.5250(9) . ?
C6 C19 1.5309(8) . ?
C6 C13 1.5346(8) . ?
C7 C12 1.3925(9) . ?
C7 C8 1.4004(9) . ?
C8 C9 1.3893(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.3910(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.3850(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.3974(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.3958(9) . ?
C13 C18 1.3994(9) . ?
C14 C15 1.3964(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.3884(11) . ?
C15 H15 0.9500 . ?
C16 C17 1.3885(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.3926(9) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.3921(9) . ?
C19 C24 1.3999(9) . ?
C20 C21 1.3960(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.3884(10) . ?
C21 H21 0.9500 . ?
C22 C23 1.3924(11) . ?
C22 H22 0.9500 . ?
C23 C24 1.3904(10) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C6 112.32(5) . . ?
C3 N1 O1 110.28(6) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 C1 124.10(8) . . ?
O2 C2 C3 117.35(8) . . ?
C1 C2 C3 118.55(7) . . ?
N1 C3 C4 117.24(7) . . ?
N1 C3 C2 124.15(6) . . ?
C4 C3 C2 118.49(6) . . ?
O3 C4 C5 123.34(8) . . ?
O3 C4 C3 118.15(8) . . ?
C5 C4 C3 118.51(7) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C4 C5 H5D 109.5 . . ?
C4 C5 H5E 109.5 . . ?
H5D C5 H5E 109.5 . . ?
C4 C5 H5F 109.5 . . ?
H5D C5 H5F 109.5 . . ?
H5E C5 H5F 109.5 . . ?
O1 C6 C7 108.60(5) . . ?
O1 C6 C19 100.90(4) . . ?
C7 C6 C19 111.29(5) . . ?
O1 C6 C13 111.02(5) . . ?
C7 C6 C13 113.14(5) . . ?
C19 C6 C13 111.21(5) . . ?
C12 C7 C8 118.72(6) . . ?
C12 C7 C6 121.84(5) . . ?
C8 C7 C6 119.32(5) . . ?
C9 C8 C7 120.61(6) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.20(6) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C11 C10 C9 119.68(6) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.24(6) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 120.53(6) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C18 118.03(6) . . ?
C14 C13 C6 120.77(5) . . ?
C18 C13 C6 121.15(5) . . ?
C13 C14 C15 121.14(6) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 120.22(7) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.13(6) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 120.73(6) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C17 C18 C13 120.72(6) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C20 C19 C24 118.83(6) . . ?
C20 C19 C6 121.42(5) . . ?
C24 C19 C6 119.74(5) . . ?
C19 C20 C21 120.57(6) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 120.24(6) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 119.56(6) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 120.22(6) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C19 120.57(6) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 H24 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 O1 N1 C3 -165.37(6) . . . . ?
O1 N1 C3 C4 -177.78(6) . . . . ?
O1 N1 C3 C2 6.29(10) . . . . ?
O2 C2 C3 N1 101.94(10) . . . . ?
C1 C2 C3 N1 -77.31(10) . . . . ?
O2 C2 C3 C4 -73.94(10) . . . . ?
C1 C2 C3 C4 106.80(9) . . . . ?
N1 C3 C4 O3 172.91(8) . . . . ?
C2 C3 C4 O3 -10.92(11) . . . . ?
N1 C3 C4 C5 -7.46(11) . . . . ?
C2 C3 C4 C5 168.71(8) . . . . ?
N1 O1 C6 C7 51.51(6) . . . . ?
N1 O1 C6 C19 168.57(5) . . . . ?
N1 O1 C6 C13 -73.48(6) . . . . ?
O1 C6 C7 C12 -146.19(6) . . . . ?
C19 C6 C7 C12 103.61(7) . . . . ?
C13 C6 C7 C12 -22.45(8) . . . . ?
O1 C6 C7 C8 37.68(7) . . . . ?
C19 C6 C7 C8 -72.52(7) . . . . ?
C13 C6 C7 C8 161.42(5) . . . . ?
C12 C7 C8 C9 1.09(10) . . . . ?
C6 C7 C8 C9 177.34(6) . . . . ?
C7 C8 C9 C10 -0.32(10) . . . . ?
C8 C9 C10 C11 -0.70(11) . . . . ?
C9 C10 C11 C12 0.94(11) . . . . ?
C8 C7 C12 C11 -0.85(10) . . . . ?
C6 C7 C12 C11 -177.01(6) . . . . ?
C10 C11 C12 C7 -0.15(11) . . . . ?
O1 C6 C13 C14 -127.70(6) . . . . ?
C7 C6 C13 C14 109.90(7) . . . . ?
C19 C6 C13 C14 -16.20(8) . . . . ?
O1 C6 C13 C18 54.85(7) . . . . ?
C7 C6 C13 C18 -67.55(7) . . . . ?
C19 C6 C13 C18 166.34(6) . . . . ?
C18 C13 C14 C15 -1.15(11) . . . . ?
C6 C13 C14 C15 -178.68(7) . . . . ?
C13 C14 C15 C16 -0.48(12) . . . . ?
C14 C15 C16 C17 1.28(12) . . . . ?
C15 C16 C17 C18 -0.45(11) . . . . ?
C16 C17 C18 C13 -1.21(11) . . . . ?
C14 C13 C18 C17 1.98(10) . . . . ?
C6 C13 C18 C17 179.50(6) . . . . ?
O1 C6 C19 C20 -139.77(6) . . . . ?
C7 C6 C19 C20 -24.70(8) . . . . ?
C13 C6 C19 C20 102.42(7) . . . . ?
O1 C6 C19 C24 41.70(7) . . . . ?
C7 C6 C19 C24 156.77(6) . . . . ?
C13 C6 C19 C24 -76.11(7) . . . . ?
C24 C19 C20 C21 -1.14(10) . . . . ?
C6 C19 C20 C21 -179.68(6) . . . . ?
C19 C20 C21 C22 0.02(10) . . . . ?
C20 C21 C22 C23 0.79(11) . . . . ?
C21 C22 C23 C24 -0.47(12) . . . . ?
C22 C23 C24 C19 -0.66(12) . . . . ?
C20 C19 C24 C23 1.46(10) . . . . ?
C6 C19 C24 C23 -179.97(6) . . . . ?

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.060

