# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

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

data_vl575
_database_code_depnum_ccdc_archive 'CCDC 2149743'
loop_
_audit_author_name
_audit_author_address
'Marek Belis'
;Ghent University
Belgium
;
_audit_update_record             
;
2022-02-02 deposited with the CCDC.	2022-05-18 downloaded from the CCDC.
;
_audit_creation_date             2022-01-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        VL575
_chemical_formula_moiety         'C22 H27 N O5'
_chemical_formula_sum            'C22 H27 N O5'
_chemical_formula_weight         385.45
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4056(2)
_cell_length_b                   9.4530(3)
_cell_length_c                   15.2930(5)
_cell_angle_alpha                84.544(2)
_cell_angle_beta                 81.654(3)
_cell_angle_gamma                83.321(3)
_cell_volume                     1048.73(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9058
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6590
_cell_measurement_theta_min      2.9080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.315
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_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    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             412
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -3 -2 0.1065
0 -5 -7 0.0734
5 1 0 0.1105
1 5 7 0.1137
-4 1 3 0.1359
-4 -4 -4 0.1116
-4 0 -8 0.1444
1 5 -4 0.1554
4 4 3 0.0905
0 -4 6 0.1363

_exptl_crystal_preparation       Synthesis
_exptl_crystal_recrystallization_method 'Hexane diffusion in CDCl3'
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.281
_exptl_crystal_size_min          0.207
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0126
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19741
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.926
_diffrn_reflns_theta_min         2.930
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  31.00   1.00    1.00    --  -41.68  57.00 -60.00  101
  2  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 150.00  101
  3  ω     27.00  98.00   1.00    1.00    --   41.68-125.00-180.00   71
  4  ω    -21.00  74.00   1.00    1.00    --   41.68 -77.00  30.00   95
  5  ω     23.00 107.00   1.00    2.00    --  106.01 -94.00  60.00   84
  6  ω     28.00 108.00   1.00    2.00    --  106.01-107.00-112.00   80
  7  ω     97.00 178.00   1.00    2.00    --  106.01 125.00 -60.00   81
  8  ω    103.00 178.00   1.00    2.00    --  106.01  77.00  90.00   75
  9  ω    103.00 178.00   1.00    2.00    --  106.01  77.00   0.00   75
 10  ω     23.00 107.00   1.00    2.00    --  106.01 -94.00 120.00   84
 11  ω     33.00 132.00   1.00    2.00    --  106.01 -45.00 -60.00   99
 12  ω     97.00 178.00   1.00    2.00    --  106.01 125.00  30.00   81
 13  ω     80.00 178.00   1.00    2.00    --  106.01  45.00 150.00   98
 14  ω     80.00 178.00   1.00    2.00    --  106.01  45.00-120.00   98
 15  ω     23.00 107.00   1.00    2.00    --  106.01 -94.00 -30.00   84
 16  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  60.00  101
 17  ω    -66.00  33.00   1.00    1.00    --  -41.68  38.00-150.00   99
 18  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -30.00  101
 19  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-120.00  101
 20  ω     77.00 178.00   1.00    2.00    --  106.01  61.00  30.00  101
 21  ω     77.00 178.00   1.00    2.00    --  106.01  61.00-180.00  101
 22  ω     53.00 178.00   1.00    2.00    --  106.01  15.00  60.00  125
 23  ω     77.00 178.00   1.00    2.00    --  106.01  61.00  60.00  101
 24  ω     80.00 178.00   1.00    2.00    --  106.01  45.00 -60.00   98
 25  ω     77.00 178.00   1.00    2.00    --  106.01  61.00 -90.00  101
 26  ω     80.00 178.00   1.00    2.00    --  106.01  45.00 -30.00   98
 27  ω     77.00 178.00   1.00    2.00    --  106.01  61.00  90.00  101
 28  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -90.00  101
 29  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-150.00  101
 30  ω   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00 -30.00   99
 31  ω     14.00 115.00   1.00    1.00    --   41.68  57.00 150.00  101
 32  ω     77.00 159.00   1.00    2.00    --  106.01  61.00   0.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3463
_reflns_number_total             4169
_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       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.086
_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)+(0.0935P)²+0.2368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1717
_refine_ls_wR_factor_ref         0.1810
_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. Restrained distances
 C18-C19
 1.51 with sigma of 0.003
 O5-C21B
 1.457 with sigma of 0.01
 O5-C21A
 1.457 with sigma of 0.01
 C22B-C21B = C21A-C22A
 1.491 with sigma of 0.01
 C20-C21A = C20-C21B
 2.373 with sigma of 0.02
 O5-C22A = O5-C22B
 2.376 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C21A) = Uanis(C21B)
Uanis(C22A) = Uanis(C22B)
4. Others
 Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(C22B)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B), C18(H18A,H18B), C21B(H21A,H21B),
 C21A(H21C,H21D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C22B(H22A,H22B,
 H22C), C22A(H22D,H22E,H22F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.7960(2) 0.47094(15) 0.57284(8) 0.0699(4) Uani 1 1 d . . . . .
O2 O 0.3478(3) 0.5676(2) 0.07032(11) 0.0944(5) Uani 1 1 d . . . . .
O3 O 0.4684(3) 0.7762(2) 0.03457(11) 0.1003(6) Uani 1 1 d . . . . .
O4 O 0.5897(3) 0.88267(19) 0.21008(13) 0.1040(6) Uani 1 1 d . . . . .
O5 O 0.3089(3) 0.8158(2) 0.23508(16) 0.1166(7) Uani 1 1 d D . . . .
N1 N 0.71805(19) 0.50232(14) 0.43434(9) 0.0543(4) Uani 1 1 d . . . . .
C1 C 0.7053(2) 0.35767(17) 0.42157(12) 0.0537(4) Uani 1 1 d . . . . .
C2 C 0.7293(3) 0.23831(19) 0.48088(14) 0.0640(5) Uani 1 1 d . . . . .
H2 H 0.758429 0.246783 0.537163 0.077 Uiso 1 1 calc R U . . .
C3 C 0.7084(3) 0.1068(2) 0.45355(17) 0.0769(6) Uani 1 1 d . . . . .
H3 H 0.724358 0.025567 0.492131 0.092 Uiso 1 1 calc R U . . .
C4 C 0.6645(3) 0.0932(2) 0.37027(17) 0.0811(6) Uani 1 1 d . . . . .
H4 H 0.649979 0.003510 0.353620 0.097 Uiso 1 1 calc R U . . .
C5 C 0.6421(3) 0.2125(2) 0.31151(15) 0.0700(5) Uani 1 1 d . . . . .
H5 H 0.613028 0.203231 0.255314 0.084 Uiso 1 1 calc R U . . .
C6 C 0.6630(2) 0.34536(18) 0.33679(12) 0.0563(4) Uani 1 1 d . . . . .
C7 C 0.6490(2) 0.48913(19) 0.28613(11) 0.0562(4) Uani 1 1 d . . . . .
C8 C 0.6885(3) 0.59243(19) 0.35268(12) 0.0599(4) Uani 1 1 d . . . . .
H8 H 0.594365 0.673514 0.361650 0.072 Uiso 1 1 calc R U . . .
C9 C 0.8621(3) 0.6297(3) 0.29123(15) 0.0785(6) Uani 1 1 d . . . . .
H9A H 0.974578 0.596647 0.315837 0.094 Uiso 1 1 calc R U . . .
H9B H 0.859417 0.730251 0.270960 0.094 Uiso 1 1 calc R U . . .
C10 C 0.8217(3) 0.5348(2) 0.22063(13) 0.0671(5) Uani 1 1 d . . . . .
C11 C 0.7426(3) 0.6170(2) 0.14082(13) 0.0704(5) Uani 1 1 d . . . . .
H11A H 0.764727 0.559200 0.090477 0.085 Uiso 1 1 calc R U . . .
H11B H 0.800515 0.704347 0.124219 0.085 Uiso 1 1 calc R U . . .
C12 C 0.5349(3) 0.6522(2) 0.16810(12) 0.0634(5) Uani 1 1 d . . . . .
C13 C 0.4832(2) 0.5279(2) 0.23703(12) 0.0606(4) Uani 1 1 d . . . . .
H13A H 0.375310 0.557662 0.277688 0.073 Uiso 1 1 calc R U . . .
H13B H 0.458328 0.446872 0.207863 0.073 Uiso 1 1 calc R U . . .
C14 C 0.7665(2) 0.55103(19) 0.50771(12) 0.0559(4) Uani 1 1 d . . . . .
C15 C 0.7808(3) 0.7083(2) 0.50497(15) 0.0695(5) Uani 1 1 d . . . . .
H15A H 0.864160 0.736625 0.453920 0.104 Uiso 1 1 calc R U . . .
H15B H 0.825323 0.729282 0.557699 0.104 Uiso 1 1 calc R U . . .
H15C H 0.661958 0.759586 0.501539 0.104 Uiso 1 1 calc R U . . .
C16 C 0.9734(3) 0.4199(3) 0.19385(19) 0.0962(8) Uani 1 1 d . . . . .
H16A H 1.013305 0.368303 0.245990 0.144 Uiso 1 1 calc R U . . .
H16B H 1.074624 0.462900 0.159303 0.144 Uiso 1 1 calc R U . . .
H16C H 0.928799 0.355269 0.159224 0.144 Uiso 1 1 calc R U . . .
C17 C 0.4351(3) 0.6575(3) 0.08718(13) 0.0716(5) Uani 1 1 d . . . . .
C18 C 0.3874(5) 0.7976(4) -0.04700(17) 0.1160(10) Uani 1 1 d D . . . .
H18A H 0.367150 0.706224 -0.065779 0.139 Uiso 1 1 calc R U . . .
H18B H 0.469533 0.843667 -0.093401 0.139 Uiso 1 1 calc R U . . .
C19 C 0.2094(6) 0.8889(6) -0.0314(3) 0.179(2) Uani 1 1 d D . . . .
H19A H 0.119373 0.833950 0.003278 0.269 Uiso 1 1 calc R U . . .
H19B H 0.168924 0.922426 -0.087330 0.269 Uiso 1 1 calc R U . . .
H19C H 0.225326 0.969067 -0.000265 0.269 Uiso 1 1 calc R U . . .
C20 C 0.4867(4) 0.7964(2) 0.20613(14) 0.0797(6) Uani 1 1 d D . . . .
C21B C 0.2710(17) 0.9729(9) 0.2482(8) 0.125(2) Uani 0.378(5) 1 d D . P A 1
H21A H 0.368799 1.005145 0.274597 0.150 Uiso 0.378(5) 1 calc R U P A 1
H21B H 0.260810 1.027921 0.191940 0.150 Uiso 0.378(5) 1 calc R U P A 1
C22B C 0.1000(15) 0.9891(11) 0.3065(7) 0.147(2) Uani 0.378(5) 1 d D . P A 1
H22A H 0.074067 1.086538 0.321205 0.220 Uiso 0.378(5) 1 calc R U P A 1
H22B H 0.109061 0.927594 0.359756 0.220 Uiso 0.378(5) 1 calc R U P A 1
H22C H 0.003044 0.963914 0.277525 0.220 Uiso 0.378(5) 1 calc R U P A 1
C21A C 0.2261(12) 0.9338(7) 0.2878(4) 0.125(2) Uani 0.622(5) 1 d D . P A 2
H21C H 0.317971 0.981691 0.309273 0.150 Uiso 0.622(5) 1 calc R U P A 2
H21D H 0.138703 0.902439 0.337335 0.150 Uiso 0.622(5) 1 calc R U P A 2
C22A C 0.1351(10) 1.0245(7) 0.2198(4) 0.147(2) Uani 0.622(5) 1 d D . P A 2
H22D H 0.226060 1.056767 0.173227 0.220 Uiso 0.622(5) 1 calc R U P A 2
H22E H 0.065259 1.105483 0.246123 0.220 Uiso 0.622(5) 1 calc R U P A 2
H22F H 0.054683 0.970351 0.195811 0.220 Uiso 0.622(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 C14 1.222(2) . ?
O2 C17 1.194(3) . ?
O3 C17 1.342(3) . ?
O3 C18 1.448(3) . ?
O4 C20 1.191(3) . ?
O5 C20 1.324(3) . ?
O5 C21B 1.506(8) . ?
O5 C21A 1.462(5) . ?
N1 C1 1.415(2) . ?
N1 C8 1.472(2) . ?
N1 C14 1.361(2) . ?
C1 C2 1.390(2) . ?
C1 C6 1.395(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(3) . ?
C6 C7 1.499(2) . ?
C7 C8 1.555(3) . ?
C7 C10 1.581(2) . ?
C7 C13 1.522(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.534(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.550(3) . ?
C10 C11 1.536(3) . ?
C10 C16 1.509(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.540(3) . ?
C12 C13 1.546(3) . ?
C12 C17 1.524(3) . ?
C12 C20 1.517(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.498(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.490(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C21B H21A 0.9700 . ?
C21B H21B 0.9700 . ?
C21B C22B 1.441(9) . ?
C22B H22A 0.9600 . ?
C22B H22B 0.9600 . ?
C22B H22C 0.9600 . ?
C21A H21C 0.9700 . ?
C21A H21D 0.9700 . ?
C21A C22A 1.473(7) . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?

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
C17 O3 C18 117.2(2) . . ?
C20 O5 C21B 104.7(5) . . ?
C20 O5 C21A 122.9(4) . . ?
C1 N1 C8 109.77(13) . . ?
C14 N1 C1 125.72(14) . . ?
C14 N1 C8 124.27(14) . . ?
C2 C1 N1 128.26(16) . . ?
C2 C1 C6 121.28(16) . . ?
C6 C1 N1 110.46(14) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 C1 117.86(19) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.52(19) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.18(19) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.62(19) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C7 110.32(15) . . ?
C5 C6 C1 119.53(17) . . ?
C5 C6 C7 130.15(17) . . ?
C6 C7 C8 103.75(13) . . ?
C6 C7 C10 118.64(15) . . ?
C6 C7 C13 116.95(15) . . ?
C8 C7 C10 89.26(13) . . ?
C13 C7 C8 118.82(16) . . ?
C13 C7 C10 106.76(14) . . ?
N1 C8 C7 105.67(13) . . ?
N1 C8 H8 114.0 . . ?
N1 C8 C9 116.01(15) . . ?
C7 C8 H8 114.0 . . ?
C9 C8 C7 90.46(15) . . ?
C9 C8 H8 114.0 . . ?
C8 C9 H9A 113.4 . . ?
C8 C9 H9B 113.4 . . ?
C8 C9 C10 91.22(14) . . ?
H9A C9 H9B 110.7 . . ?
C10 C9 H9A 113.4 . . ?
C10 C9 H9B 113.4 . . ?
C9 C10 C7 88.89(15) . . ?
C11 C10 C7 105.01(14) . . ?
C11 C10 C9 114.81(18) . . ?
C16 C10 C7 118.01(17) . . ?
C16 C10 C9 115.05(19) . . ?
C16 C10 C11 112.74(19) . . ?
C10 C11 H11A 110.2 . . ?
C10 C11 H11B 110.2 . . ?
C10 C11 C12 107.69(15) . . ?
H11A C11 H11B 108.5 . . ?
C12 C11 H11A 110.2 . . ?
C12 C11 H11B 110.2 . . ?
C11 C12 C13 103.63(15) . . ?
C17 C12 C11 109.76(16) . . ?
C17 C12 C13 112.02(17) . . ?
C20 C12 C11 112.87(18) . . ?
C20 C12 C13 112.02(16) . . ?
C20 C12 C17 106.64(16) . . ?
C7 C13 C12 105.44(14) . . ?
C7 C13 H13A 110.7 . . ?
C7 C13 H13B 110.7 . . ?
C12 C13 H13A 110.7 . . ?
C12 C13 H13B 110.7 . . ?
H13A C13 H13B 108.8 . . ?
O1 C14 N1 121.84(16) . . ?
O1 C14 C15 121.52(17) . . ?
N1 C14 C15 116.64(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O2 C17 O3 124.61(19) . . ?
O2 C17 C12 125.8(2) . . ?
O3 C17 C12 109.47(19) . . ?
O3 C18 H18A 109.9 . . ?
O3 C18 H18B 109.9 . . ?
O3 C18 C19 108.9(3) . . ?
H18A C18 H18B 108.3 . . ?
C19 C18 H18A 109.9 . . ?
C19 C18 H18B 109.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 O5 123.3(2) . . ?
O4 C20 C12 126.5(2) . . ?
O5 C20 C12 110.2(2) . . ?
O5 C21B H21A 110.6 . . ?
O5 C21B H21B 110.6 . . ?
H21A C21B H21B 108.7 . . ?
C22B C21B O5 105.9(8) . . ?
C22B C21B H21A 110.6 . . ?
C22B C21B H21B 110.6 . . ?
C21B C22B H22A 109.5 . . ?
C21B C22B H22B 109.5 . . ?
C21B C22B H22C 109.5 . . ?
H22A C22B H22B 109.5 . . ?
H22A C22B H22C 109.5 . . ?
H22B C22B H22C 109.5 . . ?
O5 C21A H21C 111.9 . . ?
O5 C21A H21D 111.9 . . ?
O5 C21A C22A 99.4(4) . . ?
H21C C21A H21D 109.6 . . ?
C22A C21A H21C 111.9 . . ?
C22A C21A H21D 111.9 . . ?
C21A C22A H22D 109.5 . . ?
C21A C22A H22E 109.5 . . ?
C21A C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 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
N1 C1 C2 C3 179.54(18) . . . . ?
N1 C1 C6 C5 -179.17(16) . . . . ?
N1 C1 C6 C7 1.2(2) . . . . ?
N1 C8 C9 C10 110.83(16) . . . . ?
C1 N1 C8 C7 1.69(18) . . . . ?
C1 N1 C8 C9 -96.71(18) . . . . ?
C1 N1 C14 O1 -3.5(3) . . . . ?
C1 N1 C14 C15 176.85(16) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C6 C7 C8 -0.15(19) . . . . ?
C1 C6 C7 C10 96.66(19) . . . . ?
C1 C6 C7 C13 -133.07(17) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C2 C1 C6 C7 -178.70(16) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.5(3) . . . . ?
C4 C5 C6 C7 179.04(19) . . . . ?
C5 C6 C7 C8 -179.69(19) . . . . ?
C5 C6 C7 C10 -82.9(2) . . . . ?
C5 C6 C7 C13 47.4(3) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C6 C7 C8 N1 -0.92(17) . . . . ?
C6 C7 C8 C9 116.32(15) . . . . ?
C6 C7 C10 C9 -102.28(18) . . . . ?
C6 C7 C10 C11 142.29(17) . . . . ?
C6 C7 C10 C16 15.7(3) . . . . ?
C6 C7 C13 C12 -161.64(15) . . . . ?
C7 C8 C9 C10 3.11(14) . . . . ?
C7 C10 C11 C12 13.9(2) . . . . ?
C8 N1 C1 C2 178.06(18) . . . . ?
C8 N1 C1 C6 -1.9(2) . . . . ?
C8 N1 C14 O1 -177.29(16) . . . . ?
C8 N1 C14 C15 3.1(3) . . . . ?
C8 C7 C10 C9 3.02(14) . . . . ?
C8 C7 C10 C11 -112.41(16) . . . . ?
C8 C7 C10 C16 121.0(2) . . . . ?
C8 C7 C13 C12 72.63(19) . . . . ?
C8 C9 C10 C7 -3.06(14) . . . . ?
C8 C9 C10 C11 102.99(17) . . . . ?
C8 C9 C10 C16 -123.69(18) . . . . ?
C9 C10 C11 C12 -81.9(2) . . . . ?
C10 C7 C8 N1 -120.29(14) . . . . ?
C10 C7 C8 C9 -3.05(14) . . . . ?
C10 C7 C13 C12 -26.0(2) . . . . ?
C10 C11 C12 C13 -29.8(2) . . . . ?
C10 C11 C12 C17 -149.60(18) . . . . ?
C10 C11 C12 C20 91.6(2) . . . . ?
C11 C12 C13 C7 34.23(19) . . . . ?
C11 C12 C17 O2 104.2(3) . . . . ?
C11 C12 C17 O3 -72.5(2) . . . . ?
C11 C12 C20 O4 5.5(3) . . . . ?
C11 C12 C20 O5 -174.84(18) . . . . ?
C13 C7 C8 N1 130.92(16) . . . . ?
C13 C7 C8 C9 -111.84(17) . . . . ?
C13 C7 C10 C9 122.99(16) . . . . ?
C13 C7 C10 C11 7.6(2) . . . . ?
C13 C7 C10 C16 -119.0(2) . . . . ?
C13 C12 C17 O2 -10.3(3) . . . . ?
C13 C12 C17 O3 172.98(17) . . . . ?
C13 C12 C20 O4 122.0(2) . . . . ?
C13 C12 C20 O5 -58.3(2) . . . . ?
C14 N1 C1 C2 3.6(3) . . . . ?
C14 N1 C1 C6 -176.38(16) . . . . ?
C14 N1 C8 C7 176.30(15) . . . . ?
C14 N1 C8 C9 77.9(2) . . . . ?
C16 C10 C11 C12 143.70(19) . . . . ?
C17 O3 C18 C19 94.5(4) . . . . ?
C17 C12 C13 C7 152.48(16) . . . . ?
C17 C12 C20 O4 -115.1(2) . . . . ?
C17 C12 C20 O5 64.6(2) . . . . ?
C18 O3 C17 O2 2.0(4) . . . . ?
C18 O3 C17 C12 178.7(2) . . . . ?
C20 O5 C21B C22B -160.9(9) . . . . ?
C20 O5 C21A C22A 105.7(6) . . . . ?
C20 C12 C13 C7 -87.7(2) . . . . ?
C20 C12 C17 O2 -133.2(2) . . . . ?
C20 C12 C17 O3 50.1(2) . . . . ?
C21B O5 C20 O4 14.0(6) . . . . ?
C21B O5 C20 C12 -165.6(5) . . . . ?
C21A O5 C20 O4 -10.3(5) . . . . ?
C21A O5 C20 C12 170.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
