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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_uvar379
_database_code_depnum_ccdc_archive 'CCDC 2210061'
loop_
_audit_author_name
_audit_author_address
'Egor Lipatov'
;A N Nesmeyanov Insitute of Organoelement Chemistry of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_audit_creation_date             2022-11-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 N3 O3'
_chemical_formula_sum            'C22 H21 N3 O3'
_chemical_formula_weight         375.42
_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'
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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.13780(10)
_cell_length_b                   24.1686(4)
_cell_length_c                   10.0882(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.5230(10)
_cell_angle_gamma                90
_cell_volume                     1845.79(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7541
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.8153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1238 before and 0.0503 after correction.
The Ratio of minimum to maximum transmission is 0.9456.
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    1.351
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            24713
_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         28.992
_diffrn_reflns_theta_min         2.328
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4028
_reflns_number_total             4899
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.024
_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)+(0.0514P)²+0.7226P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O3(H3)
2.b Ternary CH refined with riding coordinates:
 C19(H19)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C10(H10), C12(H12), C1(H1), C7(H7), C9(H9), C6(H6), C8(H8),
 C5(H5)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_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
O3 O 0.57934(11) 0.69922(3) 0.47185(9) 0.01860(19) Uani 1 1 d . . . . .
H3 H 0.6914 0.6737 0.5169 0.022 Uiso 1 1 d R U . . .
O2 O 0.95426(11) 0.56785(4) 0.70928(9) 0.01840(19) Uani 1 1 d . . . . .
O1 O 0.84556(12) 0.64473(4) 0.58407(10) 0.0207(2) Uani 1 1 d . . . . .
N2 N 0.43932(13) 0.66393(4) 0.42231(10) 0.0143(2) Uani 1 1 d . . . . .
N1 N 0.23644(13) 0.60598(4) 0.41394(10) 0.0141(2) Uani 1 1 d . . . . .
N3 N 0.89951(14) 0.52342(4) 0.77684(11) 0.0179(2) Uani 1 1 d . . . . .
C16 C 0.39339(15) 0.62659(5) 0.49999(12) 0.0135(2) Uani 1 1 d . . . . .
C13 C 0.73271(15) 0.53415(5) 0.75490(12) 0.0140(2) Uani 1 1 d . . . . .
C15 C 0.81578(16) 0.60307(5) 0.64994(12) 0.0159(2) Uani 1 1 d . . . . .
C11 C 0.50479(16) 0.66171(5) 0.74876(12) 0.0139(2) Uani 1 1 d . . . . .
C19 C 0.49628(15) 0.61156(5) 0.65277(12) 0.0130(2) Uani 1 1 d . . . . .
H19 H 0.4229 0.5834 0.6783 0.016 Uiso 1 1 calc R U . . .
C14 C 0.67045(15) 0.58351(5) 0.67646(12) 0.0135(2) Uani 1 1 d . . . . .
C18 C 0.18582(16) 0.63109(5) 0.28091(12) 0.0163(2) Uani 1 1 d . . . . .
C3 C 0.63643(15) 0.49335(5) 0.80829(12) 0.0142(2) Uani 1 1 d . . . . .
C4 C 0.47976(16) 0.46970(5) 0.71637(13) 0.0171(2) Uani 1 1 d . . . . .
H4 H 0.4307 0.4813 0.6198 0.021 Uiso 1 1 calc R U . . .
C2 C 0.70878(16) 0.47539(5) 0.94962(13) 0.0172(2) Uani 1 1 d . . . . .
H2 H 0.8162 0.4909 1.0127 0.021 Uiso 1 1 calc R U . . .
C10 C 0.66300(16) 0.68357(5) 0.84113(12) 0.0168(2) Uani 1 1 d . . . . .
H10 H 0.7717 0.6679 0.8452 0.020 Uiso 1 1 calc R U . . .
C17 C 0.31513(16) 0.66761(5) 0.28601(12) 0.0157(2) Uani 1 1 d . . . . .
C12 C 0.34601(17) 0.68495(5) 0.74516(13) 0.0185(2) Uani 1 1 d . . . . .
H12 H 0.2369 0.6698 0.6839 0.022 Uiso 1 1 calc R U . . .
C1 C 0.62357(17) 0.43478(5) 0.99791(13) 0.0205(3) Uani 1 1 d . . . . .
H1 H 0.6731 0.4226 1.0941 0.025 Uiso 1 1 calc R U . . .
C7 C 0.34649(18) 0.73011(5) 0.83050(14) 0.0224(3) Uani 1 1 d . . . . .
H7 H 0.2380 0.7460 0.8263 0.027 Uiso 1 1 calc R U . . .
C9 C 0.66338(18) 0.72841(5) 0.92801(13) 0.0203(3) Uani 1 1 d . . . . .
H9 H 0.7722 0.7429 0.9917 0.024 Uiso 1 1 calc R U . . .
C6 C 0.46660(18) 0.41185(5) 0.90668(14) 0.0214(3) Uani 1 1 d . . . . .
H6 H 0.4082 0.3844 0.9406 0.026 Uiso 1 1 calc R U . . .
C21 C 0.01552(17) 0.61921(6) 0.16307(14) 0.0233(3) Uani 1 1 d . . . . .
H21A H -0.0033 0.5791 0.1541 0.035 Uiso 1 1 calc R U . . .
H21B H 0.0188 0.6341 0.0737 0.035 Uiso 1 1 calc R U . . .
H21C H -0.0812 0.6366 0.1837 0.035 Uiso 1 1 calc R U . . .
C8 C 0.50539(19) 0.75198(5) 0.92183(13) 0.0220(3) Uani 1 1 d . . . . .
H8 H 0.5059 0.7830 0.9799 0.026 Uiso 1 1 calc R U . . .
C20 C 0.12257(16) 0.56915(5) 0.45768(13) 0.0195(3) Uani 1 1 d . . . . .
H20A H 0.1956 0.5457 0.5366 0.029 Uiso 1 1 calc R U . . .
H20B H 0.0536 0.5458 0.3771 0.029 Uiso 1 1 calc R U . . .
H20C H 0.0423 0.5913 0.4886 0.029 Uiso 1 1 calc R U . . .
C22 C 0.33654(18) 0.70622(5) 0.17926(13) 0.0212(3) Uani 1 1 d . . . . .
H22A H 0.3459 0.7442 0.2153 0.032 Uiso 1 1 calc R U . . .
H22B H 0.2340 0.7032 0.0901 0.032 Uiso 1 1 calc R U . . .
H22C H 0.4439 0.6967 0.1618 0.032 Uiso 1 1 calc R U . . .
C5 C 0.39493(17) 0.42906(5) 0.76562(14) 0.0206(3) Uani 1 1 d . . . . .
H5 H 0.2881 0.4131 0.7027 0.025 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
O3 H3 1.0567 . ?
O3 N2 1.3630(13) . ?
O2 N3 1.4278(13) . ?
O2 C15 1.3631(14) . ?
O1 H3 1.3774 . ?
O1 C15 1.2777(14) . ?
N2 C16 1.3354(15) . ?
N2 C17 1.3785(15) . ?
N1 C16 1.3489(14) . ?
N1 C18 1.3906(15) . ?
N1 C20 1.4648(15) . ?
N3 C13 1.3184(15) . ?
C16 C19 1.5038(15) . ?
C13 C14 1.4185(15) . ?
C13 C3 1.4785(16) . ?
C15 C14 1.3877(17) . ?
C11 C19 1.5369(15) . ?
C11 C10 1.3873(17) . ?
C11 C12 1.3972(17) . ?
C19 H19 1.0000 . ?
C19 C14 1.5090(16) . ?
C18 C17 1.3599(17) . ?
C18 C21 1.4857(16) . ?
C3 C4 1.3945(16) . ?
C3 C2 1.3972(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3926(17) . ?
C2 H2 0.9500 . ?
C2 C1 1.3889(18) . ?
C10 H10 0.9500 . ?
C10 C9 1.3932(17) . ?
C17 C22 1.4826(17) . ?
C12 H12 0.9500 . ?
C12 C7 1.3891(17) . ?
C1 H1 0.9500 . ?
C1 C6 1.3868(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.3865(19) . ?
C6 H6 0.9500 . ?
C6 C5 1.3890(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C8 H8 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C5 H5 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
N2 O3 H3 105.4 . . ?
C15 O2 N3 109.07(9) . . ?
C15 O1 H3 110.1 . . ?
O3 N2 C17 122.26(10) . . ?
C16 N2 O3 125.74(10) . . ?
C16 N2 C17 111.61(10) . . ?
C16 N1 C18 109.58(10) . . ?
C16 N1 C20 125.79(10) . . ?
C18 N1 C20 124.04(10) . . ?
C13 N3 O2 104.74(9) . . ?
N2 C16 N1 105.95(10) . . ?
N2 C16 C19 126.45(10) . . ?
N1 C16 C19 127.60(10) . . ?
N3 C13 C14 113.21(11) . . ?
N3 C13 C3 117.27(10) . . ?
C14 C13 C3 129.47(11) . . ?
O2 C15 C14 109.17(10) . . ?
O1 C15 O2 115.88(10) . . ?
O1 C15 C14 134.94(11) . . ?
C10 C11 C19 122.66(11) . . ?
C10 C11 C12 119.07(11) . . ?
C12 C11 C19 118.24(10) . . ?
C16 C19 C11 109.56(9) . . ?
C16 C19 H19 105.5 . . ?
C16 C19 C14 114.09(9) . . ?
C11 C19 H19 105.5 . . ?
C14 C19 C11 115.59(9) . . ?
C14 C19 H19 105.5 . . ?
C13 C14 C19 126.06(10) . . ?
C15 C14 C13 103.81(10) . . ?
C15 C14 C19 129.34(10) . . ?
N1 C18 C21 123.16(11) . . ?
C17 C18 N1 107.20(10) . . ?
C17 C18 C21 129.60(11) . . ?
C4 C3 C13 120.57(10) . . ?
C4 C3 C2 119.43(11) . . ?
C2 C3 C13 119.85(11) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.25(11) . . ?
C5 C4 H4 119.9 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 119.98(11) . . ?
C1 C2 H2 120.0 . . ?
C11 C10 H10 119.8 . . ?
C11 C10 C9 120.41(12) . . ?
C9 C10 H10 119.8 . . ?
N2 C17 C22 121.78(11) . . ?
C18 C17 N2 105.66(10) . . ?
C18 C17 C22 132.56(11) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 C11 120.49(12) . . ?
C7 C12 H12 119.8 . . ?
C2 C1 H1 119.8 . . ?
C6 C1 C2 120.43(12) . . ?
C6 C1 H1 119.8 . . ?
C12 C7 H7 120.0 . . ?
C8 C7 C12 120.05(12) . . ?
C8 C7 H7 120.0 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.22(12) . . ?
C8 C9 H9 119.9 . . ?
C1 C6 H6 120.0 . . ?
C1 C6 C5 119.90(12) . . ?
C5 C6 H6 120.0 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.74(12) . . ?
C9 C8 H8 120.1 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.00(12) . . ?
C6 C5 H5 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 1.06 1.38 2.4311(13) 174.3 .

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
O3 N2 C16 N1 172.30(10) . . . . ?
O3 N2 C16 C19 -7.04(18) . . . . ?
O3 N2 C17 C18 -172.44(10) . . . . ?
O3 N2 C17 C22 6.91(17) . . . . ?
O2 N3 C13 C14 -0.17(13) . . . . ?
O2 N3 C13 C3 177.45(9) . . . . ?
O2 C15 C14 C13 -0.31(13) . . . . ?
O2 C15 C14 C19 169.86(11) . . . . ?
O1 C15 C14 C13 179.03(13) . . . . ?
O1 C15 C14 C19 -10.8(2) . . . . ?
N2 C16 C19 C11 65.04(15) . . . . ?
N2 C16 C19 C14 -66.33(15) . . . . ?
N1 C16 C19 C11 -114.16(13) . . . . ?
N1 C16 C19 C14 114.47(13) . . . . ?
N1 C18 C17 N2 -0.57(13) . . . . ?
N1 C18 C17 C22 -179.83(12) . . . . ?
N3 O2 C15 O1 -179.26(10) . . . . ?
N3 O2 C15 C14 0.22(13) . . . . ?
N3 C13 C14 C15 0.30(13) . . . . ?
N3 C13 C14 C19 -170.29(11) . . . . ?
N3 C13 C3 C4 -124.35(12) . . . . ?
N3 C13 C3 C2 51.21(15) . . . . ?
C16 N2 C17 C18 0.74(13) . . . . ?
C16 N2 C17 C22 -179.90(11) . . . . ?
C16 N1 C18 C17 0.23(13) . . . . ?
C16 N1 C18 C21 -177.53(11) . . . . ?
C16 C19 C14 C13 -131.10(12) . . . . ?
C16 C19 C14 C15 60.74(16) . . . . ?
C13 C3 C4 C5 176.45(11) . . . . ?
C13 C3 C2 C1 -176.38(11) . . . . ?
C15 O2 N3 C13 -0.03(12) . . . . ?
C11 C19 C14 C13 100.52(13) . . . . ?
C11 C19 C14 C15 -67.63(15) . . . . ?
C11 C10 C9 C8 -0.66(18) . . . . ?
C11 C12 C7 C8 -0.98(19) . . . . ?
C19 C11 C10 C9 -178.71(11) . . . . ?
C19 C11 C12 C7 179.61(11) . . . . ?
C14 C13 C3 C4 52.81(17) . . . . ?
C14 C13 C3 C2 -131.63(13) . . . . ?
C18 N1 C16 N2 0.22(13) . . . . ?
C18 N1 C16 C19 179.55(11) . . . . ?
C3 C13 C14 C15 -176.95(11) . . . . ?
C3 C13 C14 C19 12.45(19) . . . . ?
C3 C4 C5 C6 -0.17(19) . . . . ?
C3 C2 C1 C6 -0.04(19) . . . . ?
C4 C3 C2 C1 -0.77(18) . . . . ?
C2 C3 C4 C5 0.87(18) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C10 C11 C19 C16 -124.23(12) . . . . ?
C10 C11 C19 C14 6.34(16) . . . . ?
C10 C11 C12 C7 1.44(18) . . . . ?
C10 C9 C8 C7 1.13(19) . . . . ?
C17 N2 C16 N1 -0.60(13) . . . . ?
C17 N2 C16 C19 -179.94(11) . . . . ?
C12 C11 C19 C16 57.66(13) . . . . ?
C12 C11 C19 C14 -171.76(10) . . . . ?
C12 C11 C10 C9 -0.62(17) . . . . ?
C12 C7 C8 C9 -0.32(19) . . . . ?
C1 C6 C5 C4 -0.7(2) . . . . ?
C21 C18 C17 N2 177.00(12) . . . . ?
C21 C18 C17 C22 -2.3(2) . . . . ?
C20 N1 C16 N2 -171.30(11) . . . . ?
C20 N1 C16 C19 8.04(19) . . . . ?
C20 N1 C18 C17 171.93(11) . . . . ?
C20 N1 C18 C21 -5.84(18) . . . . ?

_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_uvar410
_database_code_depnum_ccdc_archive 'CCDC 2210575'
loop_
_audit_author_name
_audit_author_address
'Egor Lipatov'
;A N Nesmeyanov Insitute of Organoelement Chemistry of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_audit_creation_date             2022-11-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H27 N3 O6'
_chemical_formula_sum            'C25 H27 N3 O6'
_chemical_formula_weight         465.49
_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'
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      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                   8.3902(2)
_cell_length_b                   11.0278(2)
_cell_length_c                   14.1048(3)
_cell_angle_alpha                70.4870(10)
_cell_angle_beta                 84.7270(10)
_cell_angle_gamma                72.3400(10)
_cell_volume                     1172.06(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5116
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.8111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1201 before and 0.0442 after correction.
The Ratio of minimum to maximum transmission is 0.9407.
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    1.319
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15851
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         2.048
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4844
_reflns_number_total             6209
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         6209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.019
_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)+(0.0450P)²+0.4351P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1111
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O2(H2)
2.b Ternary CH refined with riding coordinates:
 C19(H19)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.64111(12) 0.28176(10) 0.38952(8) 0.0229(2) Uani 1 1 d . . . . .
O2 O 0.39206(12) 0.46652(9) 0.39103(7) 0.0176(2) Uani 1 1 d . . . . .
H2 H 0.4899 0.3970 0.3933 0.021 Uiso 1 1 d R U . . .
O3 O 0.73947(12) 0.08682(10) 0.35689(8) 0.0211(2) Uani 1 1 d . . . . .
O4 O 0.14760(13) 0.77758(10) -0.02095(7) 0.0227(2) Uani 1 1 d . . . . .
O5 O -0.09558(12) 0.67041(10) 0.06222(7) 0.0216(2) Uani 1 1 d . . . . .
O6 O -0.02588(11) 0.43077(10) 0.22787(7) 0.0172(2) Uani 1 1 d . . . . .
N1 N 0.68335(14) 0.00237(12) 0.31845(9) 0.0195(2) Uani 1 1 d . . . . .
N2 N 0.28326(13) 0.39459(11) 0.43668(8) 0.0141(2) Uani 1 1 d . . . . .
N3 N 0.12995(13) 0.26211(11) 0.46738(8) 0.0140(2) Uani 1 1 d . . . . .
C1 C 0.24484(19) -0.11204(15) 0.17314(11) 0.0227(3) Uani 1 1 d . . . . .
H1 H 0.1817 -0.1519 0.1465 0.027 Uiso 1 1 calc R U . . .
C2 C 0.22227(18) 0.02523(15) 0.13443(11) 0.0221(3) Uani 1 1 d . . . . .
H2A H 0.1437 0.0793 0.0815 0.026 Uiso 1 1 calc R U . . .
C3 C 0.31436(17) 0.08381(14) 0.17294(10) 0.0182(3) Uani 1 1 d . . . . .
H3 H 0.3003 0.1777 0.1452 0.022 Uiso 1 1 calc R U . . .
C4 C 0.42787(16) 0.00553(13) 0.25230(10) 0.0159(3) Uani 1 1 d . . . . .
C5 C 0.44926(17) -0.13294(14) 0.29054(10) 0.0195(3) Uani 1 1 d . . . . .
H5 H 0.5261 -0.1873 0.3443 0.023 Uiso 1 1 calc R U . . .
C6 C 0.35924(18) -0.19166(14) 0.25064(11) 0.0225(3) Uani 1 1 d . . . . .
H6 H 0.3758 -0.2860 0.2762 0.027 Uiso 1 1 calc R U . . .
C7 C 0.39142(17) 0.46763(13) 0.16705(10) 0.0174(3) Uani 1 1 d . . . . .
H7 H 0.5036 0.4211 0.1895 0.021 Uiso 1 1 calc R U . . .
C8 C 0.35924(17) 0.58762(14) 0.08709(10) 0.0184(3) Uani 1 1 d . . . . .
H8 H 0.4485 0.6219 0.0552 0.022 Uiso 1 1 calc R U . . .
C9 C 0.19518(17) 0.65692(13) 0.05424(9) 0.0173(3) Uani 1 1 d . . . . .
C10 C 0.06478(16) 0.60418(13) 0.10002(10) 0.0163(3) Uani 1 1 d . . . . .
C11 C 0.10049(16) 0.48355(13) 0.17937(9) 0.0145(3) Uani 1 1 d . . . . .
C12 C 0.26472(16) 0.41435(13) 0.21475(9) 0.0139(2) Uani 1 1 d . . . . .
C13 C 0.52492(16) 0.06646(13) 0.29501(10) 0.0157(3) Uani 1 1 d . . . . .
C14 C 0.47004(16) 0.19028(13) 0.31508(10) 0.0150(3) Uani 1 1 d . . . . .
C15 C 0.60987(16) 0.19791(13) 0.35527(10) 0.0175(3) Uani 1 1 d . . . . .
C16 C 0.11057(16) 0.31321(13) 0.54683(10) 0.0153(3) Uani 1 1 d . . . . .
C17 C 0.20867(16) 0.39637(13) 0.52778(10) 0.0155(3) Uani 1 1 d . . . . .
C18 C 0.23607(15) 0.31382(13) 0.40008(9) 0.0136(2) Uani 1 1 d . . . . .
C19 C 0.29458(15) 0.28445(13) 0.30385(9) 0.0134(2) Uani 1 1 d . . . . .
H19 H 0.2209 0.2345 0.2920 0.016 Uiso 1 1 calc R U . . .
C20 C 0.04737(17) 0.16695(14) 0.45871(10) 0.0185(3) Uani 1 1 d . . . . .
H20A H -0.0549 0.2163 0.4180 0.028 Uiso 1 1 calc R U . . .
H20B H 0.0188 0.1153 0.5259 0.028 Uiso 1 1 calc R U . . .
H20C H 0.1228 0.1055 0.4264 0.028 Uiso 1 1 calc R U . . .
C21 C 0.24576(18) 0.47644(14) 0.58466(10) 0.0197(3) Uani 1 1 d . . . . .
H21A H 0.3544 0.4289 0.6189 0.029 Uiso 1 1 calc R U . . .
H21B H 0.1584 0.4889 0.6346 0.029 Uiso 1 1 calc R U . . .
H21C H 0.2489 0.5644 0.5380 0.029 Uiso 1 1 calc R U . . .
C22 C -0.00109(17) 0.27707(14) 0.63327(10) 0.0209(3) Uani 1 1 d . . . . .
H22A H -0.1116 0.2888 0.6081 0.031 Uiso 1 1 calc R U . . .
H22B H -0.0119 0.3355 0.6742 0.031 Uiso 1 1 calc R U . . .
H22C H 0.0468 0.1831 0.6744 0.031 Uiso 1 1 calc R U . . .
C23 C -0.2033(2) 0.74143(18) 0.12290(12) 0.0364(4) Uani 1 1 d . . . . .
H23A H -0.1515 0.8035 0.1351 0.055 Uiso 1 1 calc R U . . .
H23B H -0.2217 0.6772 0.1873 0.055 Uiso 1 1 calc R U . . .
H23C H -0.3108 0.7923 0.0880 0.055 Uiso 1 1 calc R U . . .
C24 C -0.10471(19) 0.38055(16) 0.16857(11) 0.0250(3) Uani 1 1 d . . . . .
H24A H -0.1718 0.4562 0.1147 0.037 Uiso 1 1 calc R U . . .
H24B H -0.1772 0.3301 0.2116 0.037 Uiso 1 1 calc R U . . .
H24C H -0.0187 0.3213 0.1391 0.037 Uiso 1 1 calc R U . . .
C25 C 0.2764(2) 0.83246(16) -0.07399(11) 0.0288(3) Uani 1 1 d . . . . .
H25A H 0.2264 0.9153 -0.1286 0.043 Uiso 1 1 calc R U . . .
H25B H 0.3543 0.7672 -0.1021 0.043 Uiso 1 1 calc R U . . .
H25C H 0.3369 0.8526 -0.0276 0.043 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 C15 1.2751(17) . ?
O2 H2 0.9321 . ?
O2 N2 1.3664(14) . ?
O3 N1 1.4260(15) . ?
O3 C15 1.3643(16) . ?
O4 C9 1.3665(16) . ?
O4 C25 1.4282(19) . ?
O5 C10 1.3797(15) . ?
O5 C23 1.4280(18) . ?
O6 C11 1.3806(16) . ?
O6 C24 1.4412(17) . ?
N1 C13 1.3155(17) . ?
N2 C17 1.3802(16) . ?
N2 C18 1.3324(16) . ?
N3 C16 1.3903(16) . ?
N3 C18 1.3453(17) . ?
N3 C20 1.4624(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(2) . ?
C1 C6 1.388(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3989(18) . ?
C4 C5 1.3987(19) . ?
C4 C13 1.4731(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.3922(19) . ?
C7 C12 1.3826(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.3914(19) . ?
C9 C10 1.3992(19) . ?
C10 C11 1.3918(18) . ?
C11 C12 1.4015(17) . ?
C12 C19 1.5270(17) . ?
C13 C14 1.4176(18) . ?
C14 C15 1.3852(18) . ?
C14 C19 1.5087(17) . ?
C16 C17 1.3577(19) . ?
C16 C22 1.4883(19) . ?
C17 C21 1.4853(18) . ?
C18 C19 1.5044(17) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 O2 H2 100.5 . . ?
C15 O3 N1 109.33(10) . . ?
C9 O4 C25 117.64(12) . . ?
C10 O5 C23 114.59(11) . . ?
C11 O6 C24 114.41(10) . . ?
C13 N1 O3 104.73(10) . . ?
O2 N2 C17 123.73(11) . . ?
C18 N2 O2 124.94(11) . . ?
C18 N2 C17 111.33(11) . . ?
C16 N3 C20 125.06(11) . . ?
C18 N3 C16 109.43(11) . . ?
C18 N3 C20 125.51(11) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.33(14) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2A 120.0 . . ?
C1 C2 C3 120.02(13) . . ?
C3 C2 H2A 120.0 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.42(13) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C13 121.11(12) . . ?
C5 C4 C3 118.85(13) . . ?
C5 C4 C13 120.04(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.60(13) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.75(13) . . ?
C5 C6 H6 120.1 . . ?
C8 C7 H7 119.1 . . ?
C12 C7 H7 119.1 . . ?
C12 C7 C8 121.85(12) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.43(13) . . ?
C9 C8 H8 120.3 . . ?
O4 C9 C8 124.76(13) . . ?
O4 C9 C10 115.30(12) . . ?
C8 C9 C10 119.93(12) . . ?
O5 C10 C9 118.89(12) . . ?
O5 C10 C11 121.57(12) . . ?
C11 C10 C9 119.48(12) . . ?
O6 C11 C10 120.85(11) . . ?
O6 C11 C12 117.94(11) . . ?
C10 C11 C12 121.17(12) . . ?
C7 C12 C11 118.12(12) . . ?
C7 C12 C19 123.41(11) . . ?
C11 C12 C19 118.47(12) . . ?
N1 C13 C4 118.79(12) . . ?
N1 C13 C14 113.03(12) . . ?
C14 C13 C4 128.17(12) . . ?
C13 C14 C19 127.11(12) . . ?
C15 C14 C13 104.22(11) . . ?
C15 C14 C19 128.44(12) . . ?
O1 C15 O3 116.31(11) . . ?
O1 C15 C14 135.01(12) . . ?
O3 C15 C14 108.68(12) . . ?
N3 C16 C22 122.74(12) . . ?
C17 C16 N3 107.22(12) . . ?
C17 C16 C22 130.03(12) . . ?
N2 C17 C21 121.22(12) . . ?
C16 C17 N2 105.70(11) . . ?
C16 C17 C21 133.06(13) . . ?
N2 C18 N3 106.30(11) . . ?
N2 C18 C19 126.31(12) . . ?
N3 C18 C19 127.37(12) . . ?
C12 C19 H19 106.1 . . ?
C14 C19 C12 115.69(11) . . ?
C14 C19 H19 106.1 . . ?
C18 C19 C12 110.85(10) . . ?
C18 C19 C14 111.23(10) . . ?
C18 C19 H19 106.1 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
O5 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O6 C24 H24A 109.5 . . ?
O6 C24 H24B 109.5 . . ?
O6 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N2 C17 C16 179.87(10) . . . . ?
O2 N2 C17 C21 -1.39(18) . . . . ?
O2 N2 C18 N3 179.67(10) . . . . ?
O2 N2 C18 C19 1.15(19) . . . . ?
O3 N1 C13 C4 179.91(11) . . . . ?
O3 N1 C13 C14 0.19(15) . . . . ?
O4 C9 C10 O5 4.69(17) . . . . ?
O4 C9 C10 C11 -178.15(11) . . . . ?
O5 C10 C11 O6 -4.69(19) . . . . ?
O5 C10 C11 C12 177.53(11) . . . . ?
O6 C11 C12 C7 -179.33(11) . . . . ?
O6 C11 C12 C19 0.58(17) . . . . ?
N1 O3 C15 O1 178.70(11) . . . . ?
N1 O3 C15 C14 -1.03(15) . . . . ?
N1 C13 C14 C15 -0.80(16) . . . . ?
N1 C13 C14 C19 -175.65(12) . . . . ?
N2 C18 C19 C12 -55.09(16) . . . . ?
N2 C18 C19 C14 75.13(16) . . . . ?
N3 C16 C17 N2 0.70(13) . . . . ?
N3 C16 C17 C21 -177.82(13) . . . . ?
N3 C18 C19 C12 126.70(13) . . . . ?
N3 C18 C19 C14 -103.08(14) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C2 C3 C4 C5 1.3(2) . . . . ?
C2 C3 C4 C13 -179.14(12) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C3 C4 C13 N1 -139.00(14) . . . . ?
C3 C4 C13 C14 40.7(2) . . . . ?
C4 C5 C6 C1 -1.1(2) . . . . ?
C4 C13 C14 C15 179.51(13) . . . . ?
C4 C13 C14 C19 4.7(2) . . . . ?
C5 C4 C13 N1 40.53(18) . . . . ?
C5 C4 C13 C14 -139.80(14) . . . . ?
C6 C1 C2 C3 0.1(2) . . . . ?
C7 C8 C9 O4 177.63(12) . . . . ?
C7 C8 C9 C10 -1.5(2) . . . . ?
C7 C12 C19 C14 -21.23(18) . . . . ?
C7 C12 C19 C18 106.60(14) . . . . ?
C8 C7 C12 C11 1.04(19) . . . . ?
C8 C7 C12 C19 -178.86(12) . . . . ?
C8 C9 C10 O5 -176.09(12) . . . . ?
C8 C9 C10 C11 1.07(19) . . . . ?
C9 C10 C11 O6 178.23(11) . . . . ?
C9 C10 C11 C12 0.45(19) . . . . ?
C10 C11 C12 C7 -1.49(19) . . . . ?
C10 C11 C12 C19 178.42(11) . . . . ?
C11 C12 C19 C14 158.87(11) . . . . ?
C11 C12 C19 C18 -73.30(14) . . . . ?
C12 C7 C8 C9 0.4(2) . . . . ?
C13 C4 C5 C6 -179.67(12) . . . . ?
C13 C14 C15 O1 -178.57(16) . . . . ?
C13 C14 C15 O3 1.08(15) . . . . ?
C13 C14 C19 C12 -106.99(15) . . . . ?
C13 C14 C19 C18 125.37(14) . . . . ?
C15 O3 N1 C13 0.51(14) . . . . ?
C15 C14 C19 C12 79.38(17) . . . . ?
C15 C14 C19 C18 -48.26(18) . . . . ?
C16 N3 C18 N2 0.46(13) . . . . ?
C16 N3 C18 C19 178.96(11) . . . . ?
C17 N2 C18 N3 -0.02(14) . . . . ?
C17 N2 C18 C19 -178.54(11) . . . . ?
C18 N2 C17 C16 -0.44(14) . . . . ?
C18 N2 C17 C21 178.30(11) . . . . ?
C18 N3 C16 C17 -0.74(14) . . . . ?
C18 N3 C16 C22 179.09(11) . . . . ?
C19 C14 C15 O1 -3.8(3) . . . . ?
C19 C14 C15 O3 175.84(12) . . . . ?
C20 N3 C16 C17 179.28(11) . . . . ?
C20 N3 C16 C22 -0.88(19) . . . . ?
C20 N3 C18 N2 -179.56(11) . . . . ?
C20 N3 C18 C19 -1.06(19) . . . . ?
C22 C16 C17 N2 -179.12(12) . . . . ?
C22 C16 C17 C21 2.4(2) . . . . ?
C23 O5 C10 C9 -106.32(15) . . . . ?
C23 O5 C10 C11 76.58(17) . . . . ?
C24 O6 C11 C10 70.14(15) . . . . ?
C24 O6 C11 C12 -112.01(13) . . . . ?
C25 O4 C9 C8 4.19(19) . . . . ?
C25 O4 C9 C10 -176.64(12) . . . . ?

_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_uvar361
_database_code_depnum_ccdc_archive 'CCDC 2210062'
loop_
_audit_author_name
_audit_author_address
'Egor Lipatov'
;A N Nesmeyanov Insitute of Organoelement Chemistry of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_audit_creation_date             2022-11-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 N3 O3'
_chemical_formula_sum            'C16 H15 N3 O3'
_chemical_formula_weight         297.31
_chemical_absolute_configuration ?
_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'
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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   8.0260(2)
_cell_length_b                   18.0409(4)
_cell_length_c                   10.1247(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1466.02(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9998
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1346 before and 0.0518 after correction.
The Ratio of minimum to maximum transmission is 0.9004.
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    1.347
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_unetI/netI     0.0494
_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       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27619
_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         28.998
_diffrn_reflns_theta_min         2.258
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3337
_reflns_number_total             3887
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.022
_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)+(0.0409P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0718
_refine_ls_wR_factor_ref         0.0729
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.6(10)
 0.4(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Riding coordinates:
 N3(H3)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C5(H5), C6(H6)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_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 0.57081(16) 0.44142(7) 0.17474(12) 0.0199(3) Uani 1 1 d . . . . .
O2 O 0.43626(16) 0.81024(6) 0.40601(14) 0.0214(3) Uani 1 1 d . . . . .
O3 O 0.64186(15) 0.37200(7) 0.35230(14) 0.0196(3) Uani 1 1 d . . . . .
N1 N 0.7001(2) 0.38359(8) 0.48447(14) 0.0175(3) Uani 1 1 d . . . . .
N2 N 0.65076(16) 0.61138(8) 0.25593(14) 0.0128(3) Uani 1 1 d . . . . .
N3 N 0.54039(16) 0.61703(7) 0.45048(13) 0.0126(3) Uani 1 1 d . . . . .
H3 H 0.5010 0.5996 0.5336 0.015 Uiso 1 1 d R U . . .
C1 C 0.9218(2) 0.53816(10) 0.85533(18) 0.0181(3) Uani 1 1 d . . . . .
H1 H 0.9708 0.5565 0.9343 0.022 Uiso 1 1 calc R U . . .
C2 C 0.8377(2) 0.47076(11) 0.85595(18) 0.0192(4) Uani 1 1 d . . . . .
H2 H 0.8301 0.4428 0.9353 0.023 Uiso 1 1 calc R U . . .
C3 C 0.7652(2) 0.44429(10) 0.74149(17) 0.0161(3) Uani 1 1 d . . . . .
H3A H 0.7085 0.3980 0.7424 0.019 Uiso 1 1 calc R U . . .
C4 C 0.77458(19) 0.48511(9) 0.62435(17) 0.0135(3) Uani 1 1 d . . . . .
C5 C 0.8607(2) 0.55253(10) 0.62373(17) 0.0151(3) Uani 1 1 d . . . . .
H5 H 0.8691 0.5805 0.5445 0.018 Uiso 1 1 calc R U . . .
C6 C 0.9341(2) 0.57852(10) 0.73954(19) 0.0174(3) Uani 1 1 d . . . . .
H6 H 0.9929 0.6242 0.7390 0.021 Uiso 1 1 calc R U . . .
C7 C 0.6172(2) 0.43942(10) 0.29156(18) 0.0149(3) Uani 1 1 d . . . . .
C8 C 0.65272(18) 0.49451(9) 0.38582(16) 0.0130(3) Uani 1 1 d . . . . .
C9 C 0.7031(2) 0.45570(9) 0.50118(16) 0.0137(3) Uani 1 1 d . . . . .
C10 C 0.61755(18) 0.57177(9) 0.36658(16) 0.0121(3) Uani 1 1 d . . . . .
C11 C 0.59135(19) 0.68293(9) 0.26930(16) 0.0136(3) Uani 1 1 d . . . . .
C12 C 0.52237(19) 0.68667(8) 0.39312(17) 0.0129(3) Uani 1 1 d . . . . .
C13 C 0.4380(2) 0.74899(9) 0.45791(17) 0.0153(3) Uani 1 1 d . . . . .
C14 C 0.3540(2) 0.73386(10) 0.58761(19) 0.0205(4) Uani 1 1 d . . . . .
H14A H 0.4375 0.7190 0.6530 0.031 Uiso 1 1 calc R U . . .
H14B H 0.2724 0.6939 0.5765 0.031 Uiso 1 1 calc R U . . .
H14C H 0.2971 0.7788 0.6180 0.031 Uiso 1 1 calc R U . . .
C15 C 0.6067(2) 0.73882(10) 0.16223(18) 0.0194(4) Uani 1 1 d . . . . .
H15A H 0.7248 0.7480 0.1438 0.029 Uiso 1 1 calc R U . . .
H15B H 0.5534 0.7851 0.1900 0.029 Uiso 1 1 calc R U . . .
H15C H 0.5520 0.7202 0.0823 0.029 Uiso 1 1 calc R U . . .
C16 C 0.7493(2) 0.58539(10) 0.14307(18) 0.0186(4) Uani 1 1 d . . . . .
H16A H 0.6743 0.5712 0.0710 0.028 Uiso 1 1 calc R U . . .
H16B H 0.8161 0.5424 0.1697 0.028 Uiso 1 1 calc R U . . .
H16C H 0.8232 0.6252 0.1131 0.028 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 C7 1.241(2) . ?
O2 C13 1.224(2) . ?
O3 N1 1.4328(19) . ?
O3 C7 1.377(2) . ?
N1 C9 1.312(2) . ?
N2 C10 1.355(2) . ?
N2 C11 1.383(2) . ?
N2 C16 1.467(2) . ?
N3 H3 0.9519 . ?
N3 C10 1.331(2) . ?
N3 C12 1.392(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.391(3) . ?
C1 C6 1.384(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.398(2) . ?
C4 C5 1.399(2) . ?
C4 C9 1.472(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.407(2) . ?
C8 C9 1.421(2) . ?
C8 C10 1.435(2) . ?
C11 C12 1.372(2) . ?
C11 C15 1.486(2) . ?
C12 C13 1.467(2) . ?
C13 C14 1.501(2) . ?
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 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C7 O3 N1 109.57(12) . . ?
C9 N1 O3 105.73(13) . . ?
C10 N2 C11 110.09(14) . . ?
C10 N2 C16 125.56(14) . . ?
C11 N2 C16 124.10(14) . . ?
C10 N3 H3 121.1 . . ?
C10 N3 C12 109.62(14) . . ?
C12 N3 H3 129.2 . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.90(17) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.18(17) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3A 119.8 . . ?
C2 C3 C4 120.43(16) . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 C5 119.24(16) . . ?
C3 C4 C9 120.53(15) . . ?
C5 C4 C9 120.14(16) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.85(16) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.38(16) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O1 C7 O3 119.65(16) . . ?
O1 C7 C8 133.38(17) . . ?
O3 C7 C8 106.97(15) . . ?
C7 C8 C9 105.50(15) . . ?
C7 C8 C10 123.64(15) . . ?
C9 C8 C10 130.26(15) . . ?
N1 C9 C4 118.29(15) . . ?
N1 C9 C8 112.17(15) . . ?
C8 C9 C4 129.06(15) . . ?
N2 C10 C8 125.84(15) . . ?
N3 C10 N2 107.20(14) . . ?
N3 C10 C8 126.90(15) . . ?
N2 C11 C15 122.25(15) . . ?
C12 C11 N2 105.93(14) . . ?
C12 C11 C15 131.82(16) . . ?
N3 C12 C13 123.58(15) . . ?
C11 C12 N3 107.16(14) . . ?
C11 C12 C13 129.22(15) . . ?
O2 C13 C12 120.34(15) . . ?
O2 C13 C14 122.33(16) . . ?
C12 C13 C14 117.33(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 C7 C8 C9 -178.92(18) . . . . ?
O1 C7 C8 C10 9.2(3) . . . . ?
O3 N1 C9 C4 -173.87(13) . . . . ?
O3 N1 C9 C8 -1.11(18) . . . . ?
O3 C7 C8 C9 1.65(17) . . . . ?
O3 C7 C8 C10 -170.24(14) . . . . ?
N1 O3 C7 O1 178.10(15) . . . . ?
N1 O3 C7 C8 -2.38(17) . . . . ?
N2 C11 C12 N3 -0.66(17) . . . . ?
N2 C11 C12 C13 -178.50(15) . . . . ?
N3 C12 C13 O2 174.97(15) . . . . ?
N3 C12 C13 C14 -5.7(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C2 C3 C4 C9 177.61(15) . . . . ?
C3 C4 C5 C6 -0.7(2) . . . . ?
C3 C4 C9 N1 -30.3(2) . . . . ?
C3 C4 C9 C8 158.32(16) . . . . ?
C4 C5 C6 C1 -0.2(2) . . . . ?
C5 C4 C9 N1 146.19(16) . . . . ?
C5 C4 C9 C8 -25.2(2) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C7 O3 N1 C9 2.18(17) . . . . ?
C7 C8 C9 N1 -0.31(19) . . . . ?
C7 C8 C9 C4 171.47(16) . . . . ?
C7 C8 C10 N2 -45.5(2) . . . . ?
C7 C8 C10 N3 131.28(18) . . . . ?
C9 C4 C5 C6 -177.29(15) . . . . ?
C9 C8 C10 N2 144.72(17) . . . . ?
C9 C8 C10 N3 -38.5(3) . . . . ?
C10 N2 C11 C12 0.94(17) . . . . ?
C10 N2 C11 C15 -178.70(15) . . . . ?
C10 N3 C12 C11 0.16(17) . . . . ?
C10 N3 C12 C13 178.16(14) . . . . ?
C10 C8 C9 N1 170.84(16) . . . . ?
C10 C8 C9 C4 -17.4(3) . . . . ?
C11 N2 C10 N3 -0.84(17) . . . . ?
C11 N2 C10 C8 176.49(15) . . . . ?
C11 C12 C13 O2 -7.5(3) . . . . ?
C11 C12 C13 C14 171.83(16) . . . . ?
C12 N3 C10 N2 0.41(17) . . . . ?
C12 N3 C10 C8 -176.88(15) . . . . ?
C15 C11 C12 N3 178.93(17) . . . . ?
C15 C11 C12 C13 1.1(3) . . . . ?
C16 N2 C10 N3 173.59(15) . . . . ?
C16 N2 C10 C8 -9.1(2) . . . . ?
C16 N2 C11 C12 -173.60(15) . . . . ?
C16 N2 C11 C15 6.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.6(10)
2 0.4(10)

####################################################################### 
# 
# 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_uvar382
_database_code_depnum_ccdc_archive 'CCDC 2210576'
loop_
_audit_author_name
_audit_author_address
'Egor Lipatov'
;A N Nesmeyanov Insitute of Organoelement Chemistry of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_audit_creation_date             2022-11-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H19 Cl2 N3 O3'
_chemical_formula_sum            'C22 H19 Cl2 N3 O3'
_chemical_formula_weight         444.30
_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'
Cl Cl 0.1484 0.1585 '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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.70440(10)
_cell_length_b                   12.9589(2)
_cell_length_c                   20.3448(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.5140(10)
_cell_angle_gamma                90
_cell_volume                     2029.28(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.55
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.350
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.7783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1205 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.9027.
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    1.454
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_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            26626
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         1.864
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4673
_reflns_number_total             5389
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.050
_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     274
_refine_ls_number_reflns         5389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.027
_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)+(0.0361P)²+1.1290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0865
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O3(H3)
2.b Ternary CH refined with riding coordinates:
 C19(H19)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3A), C5(H5), C6(H6), C8(H8), C9(H9), C12(H12)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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
Cl1 Cl 0.18790(4) 0.79058(3) 0.50830(2) 0.02348(8) Uani 1 1 d . . . . .
Cl2 Cl 0.82167(4) 0.94285(3) 0.56429(2) 0.02658(9) Uani 1 1 d . . . . .
O1 O 0.58285(12) 0.64051(8) 0.28267(5) 0.0200(2) Uani 1 1 d . . . . .
O2 O 0.44213(12) 0.71997(8) 0.19772(4) 0.0203(2) Uani 1 1 d . . . . .
O3 O 0.55434(11) 0.58918(8) 0.39757(4) 0.01810(19) Uani 1 1 d . . . . .
H3 H 0.5667 0.6066 0.3542 0.022 Uiso 1 1 d R U . . .
N1 N 0.29653(15) 0.78754(9) 0.18519(5) 0.0217(2) Uani 1 1 d . . . . .
N2 N 0.37951(13) 0.57539(8) 0.40036(5) 0.0144(2) Uani 1 1 d . . . . .
N3 N 0.10559(13) 0.60344(9) 0.39316(5) 0.0165(2) Uani 1 1 d . . . . .
C1 C -0.21530(19) 0.98956(12) 0.26737(7) 0.0247(3) Uani 1 1 d . . . . .
H1 H -0.3172 1.0291 0.2736 0.030 Uiso 1 1 calc R U . . .
C2 C -0.22740(18) 0.89388(11) 0.23714(7) 0.0224(3) Uani 1 1 d . . . . .
H2 H -0.3375 0.8685 0.2218 0.027 Uiso 1 1 calc R U . . .
C3 C -0.07932(17) 0.83498(11) 0.22917(6) 0.0197(3) Uani 1 1 d . . . . .
H3A H -0.0886 0.7689 0.2091 0.024 Uiso 1 1 calc R U . . .
C4 C 0.08342(17) 0.87262(10) 0.25062(6) 0.0172(2) Uani 1 1 d . . . . .
C5 C 0.09534(19) 0.96982(11) 0.27989(7) 0.0233(3) Uani 1 1 d . . . . .
H5 H 0.2056 0.9966 0.2939 0.028 Uiso 1 1 calc R U . . .
C6 C -0.0541(2) 1.02754(12) 0.28854(8) 0.0274(3) Uani 1 1 d . . . . .
H6 H -0.0458 1.0933 0.3091 0.033 Uiso 1 1 calc R U . . .
C7 C 0.67038(17) 0.89415(10) 0.50657(6) 0.0182(2) Uani 1 1 d . . . . .
C8 C 0.71271(17) 0.88513(11) 0.44143(7) 0.0203(3) Uani 1 1 d . . . . .
H8 H 0.8221 0.9083 0.4275 0.024 Uiso 1 1 calc R U . . .
C9 C 0.59216(16) 0.84145(10) 0.39664(6) 0.0181(2) Uani 1 1 d . . . . .
H9 H 0.6213 0.8343 0.3520 0.022 Uiso 1 1 calc R U . . .
C10 C 0.43034(15) 0.80805(9) 0.41555(6) 0.0142(2) Uani 1 1 d . . . . .
C11 C 0.39140(16) 0.82320(10) 0.48117(6) 0.0154(2) Uani 1 1 d . . . . .
C12 C 0.50898(17) 0.86477(10) 0.52742(6) 0.0178(2) Uani 1 1 d . . . . .
H12 H 0.4798 0.8728 0.5720 0.021 Uiso 1 1 calc R U . . .
C13 C 0.26135(15) 0.64866(10) 0.38727(6) 0.0141(2) Uani 1 1 d . . . . .
C14 C 0.12815(18) 0.50103(11) 0.41132(6) 0.0192(3) Uani 1 1 d . . . . .
C15 C 0.30254(18) 0.48279(10) 0.41587(6) 0.0181(2) Uani 1 1 d . . . . .
C16 C 0.24060(17) 0.80829(10) 0.24396(6) 0.0172(2) Uani 1 1 d . . . . .
C17 C 0.33982(16) 0.76026(10) 0.29558(6) 0.0154(2) Uani 1 1 d . . . . .
C18 C 0.46308(16) 0.70326(10) 0.26376(6) 0.0165(2) Uani 1 1 d . . . . .
C19 C 0.29864(15) 0.75768(10) 0.36717(6) 0.0143(2) Uani 1 1 d . . . . .
H19 H 0.1876 0.7967 0.3709 0.017 Uiso 1 1 calc R U . . .
C20 C -0.06331(16) 0.65287(13) 0.38085(7) 0.0262(3) Uani 1 1 d . . . . .
H20A H -0.0480 0.7279 0.3790 0.039 Uiso 1 1 calc R U . . .
H20B H -0.1399 0.6355 0.4164 0.039 Uiso 1 1 calc R U . . .
H20C H -0.1153 0.6283 0.3389 0.039 Uiso 1 1 calc R U . . .
C21 C -0.0202(2) 0.43046(13) 0.42191(7) 0.0321(4) Uani 1 1 d . . . . .
H21A H -0.0858 0.4555 0.4589 0.048 Uiso 1 1 calc R U . . .
H21B H 0.0239 0.3610 0.4318 0.048 Uiso 1 1 calc R U . . .
H21C H -0.0964 0.4284 0.3821 0.048 Uiso 1 1 calc R U . . .
C22 C 0.4055(2) 0.38864(11) 0.43224(7) 0.0276(3) Uani 1 1 d . . . . .
H22A H 0.5029 0.3837 0.4030 0.041 Uiso 1 1 calc R U . . .
H22B H 0.3312 0.3276 0.4265 0.041 Uiso 1 1 calc R U . . .
H22C H 0.4502 0.3925 0.4780 0.041 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
Cl1 C11 1.7371(13) . ?
Cl2 C7 1.7366(13) . ?
O1 C18 1.2765(16) . ?
O2 N1 1.4370(15) . ?
O2 C18 1.3636(15) . ?
O3 H3 0.9192 . ?
O3 N2 1.3625(13) . ?
N1 C16 1.3163(17) . ?
N2 C13 1.3340(16) . ?
N2 C15 1.3812(16) . ?
N3 C13 1.3456(15) . ?
N3 C14 1.3864(18) . ?
N3 C20 1.4621(17) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(2) . ?
C1 C6 1.387(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.3972(18) . ?
C4 C5 1.3946(19) . ?
C4 C16 1.4812(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3836(18) . ?
C7 C12 1.3847(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3924(18) . ?
C9 H9 0.9500 . ?
C9 C10 1.3898(17) . ?
C10 C11 1.3949(17) . ?
C10 C19 1.5287(17) . ?
C11 C12 1.3862(18) . ?
C12 H12 0.9500 . ?
C13 C19 1.5021(17) . ?
C14 C15 1.3634(19) . ?
C14 C21 1.4867(18) . ?
C15 C22 1.4850(19) . ?
C16 C17 1.4157(17) . ?
C17 C18 1.3857(17) . ?
C17 C19 1.5047(16) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C18 O2 N1 109.22(9) . . ?
N2 O3 H3 102.5 . . ?
C16 N1 O2 104.33(10) . . ?
O3 N2 C15 123.96(11) . . ?
C13 N2 O3 124.44(10) . . ?
C13 N2 C15 111.59(10) . . ?
C13 N3 C14 109.80(11) . . ?
C13 N3 C20 125.77(12) . . ?
C14 N3 C20 124.42(11) . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.84(13) . . ?
C6 C1 H1 120.1 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.29(13) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3A 119.9 . . ?
C2 C3 C4 120.17(13) . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 C16 120.07(12) . . ?
C5 C4 C3 119.34(12) . . ?
C5 C4 C16 120.57(12) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.03(13) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.32(14) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 Cl2 119.94(10) . . ?
C8 C7 C12 121.52(12) . . ?
C12 C7 Cl2 118.55(10) . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.86(12) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.74(12) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C11 117.02(11) . . ?
C9 C10 C19 122.20(11) . . ?
C11 C10 C19 120.78(11) . . ?
C10 C11 Cl1 120.33(10) . . ?
C12 C11 Cl1 116.80(10) . . ?
C12 C11 C10 122.87(12) . . ?
C7 C12 C11 117.89(12) . . ?
C7 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
N2 C13 N3 106.01(11) . . ?
N2 C13 C19 125.93(10) . . ?
N3 C13 C19 128.01(11) . . ?
N3 C14 C21 122.64(13) . . ?
C15 C14 N3 107.20(11) . . ?
C15 C14 C21 130.16(14) . . ?
N2 C15 C22 122.33(12) . . ?
C14 C15 N2 105.39(11) . . ?
C14 C15 C22 132.27(13) . . ?
N1 C16 C4 119.98(11) . . ?
N1 C16 C17 113.34(12) . . ?
C17 C16 C4 126.62(11) . . ?
C16 C17 C19 126.72(11) . . ?
C18 C17 C16 104.29(11) . . ?
C18 C17 C19 128.19(11) . . ?
O1 C18 O2 116.79(11) . . ?
O1 C18 C17 134.43(12) . . ?
O2 C18 C17 108.76(11) . . ?
C10 C19 H19 106.3 . . ?
C13 C19 C10 110.84(10) . . ?
C13 C19 C17 109.59(10) . . ?
C13 C19 H19 106.3 . . ?
C17 C19 C10 116.85(10) . . ?
C17 C19 H19 106.3 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C21 H21A 109.5 . . ?
C14 C21 H21B 109.5 . . ?
C14 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C15 C22 H22A 109.5 . . ?
C15 C22 H22B 109.5 . . ?
C15 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
Cl1 C11 C12 C7 -178.18(10) . . . . ?
Cl2 C7 C8 C9 177.06(10) . . . . ?
Cl2 C7 C12 C11 -178.13(10) . . . . ?
O2 N1 C16 C4 -176.81(11) . . . . ?
O2 N1 C16 C17 0.70(15) . . . . ?
O3 N2 C13 N3 177.78(10) . . . . ?
O3 N2 C13 C19 0.25(19) . . . . ?
O3 N2 C15 C14 -178.24(10) . . . . ?
O3 N2 C15 C22 1.01(18) . . . . ?
N1 O2 C18 O1 176.79(11) . . . . ?
N1 O2 C18 C17 -1.98(14) . . . . ?
N1 C16 C17 C18 -1.87(15) . . . . ?
N1 C16 C17 C19 -172.21(12) . . . . ?
N2 C13 C19 C10 -52.45(16) . . . . ?
N2 C13 C19 C17 77.99(15) . . . . ?
N3 C13 C19 C10 130.57(13) . . . . ?
N3 C13 C19 C17 -99.00(14) . . . . ?
N3 C14 C15 N2 0.12(13) . . . . ?
N3 C14 C15 C22 -179.02(13) . . . . ?
C1 C2 C3 C4 -1.07(19) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C3 C4 C5 -0.15(19) . . . . ?
C2 C3 C4 C16 178.09(11) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
C3 C4 C16 N1 68.05(17) . . . . ?
C3 C4 C16 C17 -109.10(15) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C4 C16 C17 C18 175.43(12) . . . . ?
C4 C16 C17 C19 5.1(2) . . . . ?
C5 C4 C16 N1 -113.74(15) . . . . ?
C5 C4 C16 C17 69.12(18) . . . . ?
C6 C1 C2 C3 1.3(2) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C7 C12 C11 1.64(19) . . . . ?
C8 C9 C10 C11 1.99(19) . . . . ?
C8 C9 C10 C19 -178.53(12) . . . . ?
C9 C10 C11 Cl1 176.40(10) . . . . ?
C9 C10 C11 C12 -3.13(19) . . . . ?
C9 C10 C19 C13 117.34(13) . . . . ?
C9 C10 C19 C17 -9.17(17) . . . . ?
C10 C11 C12 C7 1.37(19) . . . . ?
C11 C10 C19 C13 -63.20(15) . . . . ?
C11 C10 C19 C17 170.29(11) . . . . ?
C12 C7 C8 C9 -2.7(2) . . . . ?
C13 N2 C15 C14 0.55(14) . . . . ?
C13 N2 C15 C22 179.80(11) . . . . ?
C13 N3 C14 C15 -0.75(14) . . . . ?
C13 N3 C14 C21 179.83(11) . . . . ?
C14 N3 C13 N2 1.07(13) . . . . ?
C14 N3 C13 C19 178.52(11) . . . . ?
C15 N2 C13 N3 -1.00(14) . . . . ?
C15 N2 C13 C19 -178.53(11) . . . . ?
C16 C4 C5 C6 -177.11(13) . . . . ?
C16 C17 C18 O1 -176.18(14) . . . . ?
C16 C17 C18 O2 2.27(14) . . . . ?
C16 C17 C19 C10 -118.52(14) . . . . ?
C16 C17 C19 C13 114.36(14) . . . . ?
C18 O2 N1 C16 0.79(14) . . . . ?
C18 C17 C19 C10 73.43(17) . . . . ?
C18 C17 C19 C13 -53.69(16) . . . . ?
C19 C10 C11 Cl1 -3.08(17) . . . . ?
C19 C10 C11 C12 177.39(11) . . . . ?
C19 C17 C18 O1 -6.0(2) . . . . ?
C19 C17 C18 O2 172.42(12) . . . . ?
C20 N3 C13 N2 -177.50(11) . . . . ?
C20 N3 C13 C19 0.0(2) . . . . ?
C20 N3 C14 C15 177.85(11) . . . . ?
C20 N3 C14 C21 -1.58(19) . . . . ?
C21 C14 C15 N2 179.49(13) . . . . ?
C21 C14 C15 C22 0.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
