# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_mv1119
_database_code_depnum_ccdc_archive 'CCDC 2211258'
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.	2024-05-02 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         'C23 H21 N3 O2'
_chemical_formula_sum            'C23 H21 N3 O2'
_chemical_formula_weight         371.43
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   28.6642(5)
_cell_length_b                   8.5510(2)
_cell_length_c                   17.5757(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.7010(10)
_cell_angle_gamma                90
_cell_volume                     3848.55(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8343
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.5620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1737 before and 0.0839 after correction.
The Ratio of minimum to maximum transmission is 0.6518.
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    1.282
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1568
_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  0.0668
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24875
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_min         2.511
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                4265
_reflns_number_total             5110
_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         0.361
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.030
_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)+(0.0425P)²+2.9652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1075
_refine_ls_wR_factor_ref         0.1151
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C3(H3), C5(H5), C1(H1), C9(H9), C12(H12), C8(H8), C6(H6), C2(H2)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_atom_sites_solution_hydrogens   geom
_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 0.33666(3) 0.53928(11) 0.95413(5) 0.0216(2) Uani 1 1 d . . . . .
C21 C 0.45229(4) 0.33745(16) 0.81385(8) 0.0196(2) Uani 1 1 d . . . . .
H21A H 0.4753 0.4009 0.8628 0.029 Uiso 1 1 calc R U . . .
H21B H 0.4701 0.3126 0.7791 0.029 Uiso 1 1 calc R U . . .
H21C H 0.4434 0.2403 0.8340 0.029 Uiso 1 1 calc R U . . .
O2 O 0.08819(3) 0.52827(12) 0.42906(6) 0.0223(2) Uani 1 1 d . . . . .
C11 C 0.14096(4) 0.64141(14) 0.56119(7) 0.0169(2) Uani 1 1 d . . . . .
H11 H 0.1131 0.7113 0.5517 0.020 Uiso 1 1 calc R U . . .
N3 N 0.34279(4) 0.57868(12) 0.66902(6) 0.0138(2) Uani 1 1 d . . . . .
C20 C 0.07984(5) 0.40656(19) 0.36864(8) 0.0275(3) Uani 1 1 d . . . . .
H20A H 0.0447 0.4164 0.3213 0.041 Uiso 1 1 calc R U . . .
H20B H 0.0833 0.3047 0.3963 0.041 Uiso 1 1 calc R U . . .
H20C H 0.1058 0.4151 0.3468 0.041 Uiso 1 1 calc R U . . .
N2 N 0.36225(4) 0.42125(12) 0.78038(6) 0.0144(2) Uani 1 1 d . . . . .
C3 C 0.36739(5) 0.81067(15) 0.82851(7) 0.0174(2) Uani 1 1 d . . . . .
H3 H 0.3328 0.8323 0.7868 0.021 Uiso 1 1 calc R U . . .
N1 N 0.20161(4) 0.57460(14) 0.83780(7) 0.0222(2) Uani 1 1 d . . . . .
C5 C 0.42744(5) 0.65981(17) 0.94787(8) 0.0220(3) Uani 1 1 d . . . . .
H5 H 0.4339 0.5790 0.9885 0.026 Uiso 1 1 calc R U . . .
C17 C 0.28209(4) 0.58001(14) 0.80803(7) 0.0146(2) Uani 1 1 d . . . . .
C1 C 0.45928(5) 0.86785(19) 0.89142(9) 0.0280(3) Uani 1 1 d . . . . .
H1 H 0.4875 0.9282 0.8931 0.034 Uiso 1 1 calc R U . . .
C9 C 0.17658(5) 0.43033(14) 0.51180(7) 0.0162(2) Uani 1 1 d . . . . .
H9 H 0.1730 0.3554 0.4696 0.019 Uiso 1 1 calc R U . . .
C12 C 0.18690(4) 0.65079(14) 0.63571(7) 0.0152(2) Uani 1 1 d . . . . .
H12 H 0.1903 0.7261 0.6776 0.018 Uiso 1 1 calc R U . . .
C18 C 0.33286(4) 0.59581(14) 0.88791(7) 0.0154(2) Uani 1 1 d . . . . .
C8 C 0.22284(4) 0.44237(14) 0.58606(7) 0.0150(2) Uani 1 1 d . . . . .
H8 H 0.2513 0.3764 0.5939 0.018 Uiso 1 1 calc R U . . .
C15 C 0.32631(4) 0.51493(14) 0.72424(7) 0.0133(2) Uani 1 1 d . . . . .
C22 C 0.42458(5) 0.57860(16) 0.65107(8) 0.0200(3) Uani 1 1 d . . . . .
H22A H 0.4062 0.5546 0.5901 0.030 Uiso 1 1 calc R U . . .
H22B H 0.4584 0.5248 0.6763 0.030 Uiso 1 1 calc R U . . .
H22C H 0.4302 0.6917 0.6588 0.030 Uiso 1 1 calc R U . . .
C7 C 0.22857(4) 0.54957(14) 0.64981(7) 0.0137(2) Uani 1 1 d . . . . .
C23 C 0.31679(5) 0.69530(15) 0.60251(8) 0.0192(2) Uani 1 1 d . . . . .
H23A H 0.2832 0.7236 0.6009 0.029 Uiso 1 1 calc R U . . .
H23B H 0.3109 0.6519 0.5473 0.029 Uiso 1 1 calc R U . . .
H23C H 0.3388 0.7886 0.6148 0.029 Uiso 1 1 calc R U . . .
C14 C 0.39270(4) 0.52491(14) 0.69355(7) 0.0147(2) Uani 1 1 d . . . . .
C10 C 0.13531(4) 0.52975(15) 0.49986(7) 0.0162(2) Uani 1 1 d . . . . .
C6 C 0.46851(5) 0.74726(19) 0.94946(8) 0.0285(3) Uani 1 1 d . . . . .
H6 H 0.5032 0.7247 0.9905 0.034 Uiso 1 1 calc R U . . .
C19 C 0.23685(4) 0.57726(14) 0.82341(7) 0.0162(2) Uani 1 1 d . . . . .
C16 C 0.27803(4) 0.55382(13) 0.72843(7) 0.0134(2) Uani 1 1 d . . . . .
C4 C 0.37642(4) 0.69049(14) 0.88651(7) 0.0157(2) Uani 1 1 d . . . . .
C13 C 0.40356(4) 0.42662(14) 0.76155(7) 0.0148(2) Uani 1 1 d . . . . .
C2 C 0.40866(5) 0.89959(16) 0.83110(8) 0.0232(3) Uani 1 1 d . . . . .
H2 H 0.4022 0.9822 0.7915 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 C18 1.2191(14) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 C13 1.4910(16) . ?
O2 C20 1.4282(17) . ?
O2 C10 1.3648(13) . ?
C11 H11 0.9500 . ?
C11 C12 1.3805(16) . ?
C11 C10 1.3938(17) . ?
N3 C15 1.3689(14) . ?
N3 C23 1.4607(15) . ?
N3 C14 1.3748(14) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N2 C15 1.3277(15) . ?
N2 C13 1.3661(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3874(17) . ?
C3 C2 1.3896(17) . ?
N1 C19 1.1466(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3843(18) . ?
C5 C4 1.3976(16) . ?
C17 C18 1.5071(15) . ?
C17 C19 1.4387(15) . ?
C17 C16 1.3691(16) . ?
C1 H1 0.9500 . ?
C1 C6 1.390(2) . ?
C1 C2 1.3857(19) . ?
C9 H9 0.9500 . ?
C9 C8 1.3845(16) . ?
C9 C10 1.3939(17) . ?
C12 H12 0.9500 . ?
C12 C7 1.4040(16) . ?
C18 C4 1.4976(16) . ?
C8 H8 0.9500 . ?
C8 C7 1.3991(16) . ?
C15 C16 1.4571(15) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 C14 1.4888(16) . ?
C7 C16 1.4697(15) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C14 C13 1.3775(16) . ?
C6 H6 0.9500 . ?
C2 H2 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
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
C10 O2 C20 116.83(10) . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C10 120.22(11) . . ?
C10 C11 H11 119.9 . . ?
C15 N3 C23 128.67(10) . . ?
C15 N3 C14 106.64(9) . . ?
C14 N3 C23 124.34(10) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 N2 C13 105.50(9) . . ?
C4 C3 H3 119.8 . . ?
C4 C3 C2 120.41(11) . . ?
C2 C3 H3 119.8 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 119.98(12) . . ?
C4 C5 H5 120.0 . . ?
C19 C17 C18 113.64(9) . . ?
C16 C17 C18 124.72(10) . . ?
C16 C17 C19 121.29(10) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C2 C1 C6 119.70(12) . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 119.02(11) . . ?
C10 C9 H9 120.5 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C7 120.32(11) . . ?
C7 C12 H12 119.8 . . ?
O1 C18 C17 119.23(10) . . ?
O1 C18 C4 120.84(10) . . ?
C4 C18 C17 119.77(10) . . ?
C9 C8 H8 119.3 . . ?
C9 C8 C7 121.45(11) . . ?
C7 C8 H8 119.3 . . ?
N3 C15 C16 125.67(10) . . ?
N2 C15 N3 111.56(10) . . ?
N2 C15 C16 122.51(10) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
C12 C7 C16 122.37(10) . . ?
C8 C7 C12 118.56(10) . . ?
C8 C7 C16 119.06(10) . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C14 C22 121.76(11) . . ?
N3 C14 C13 105.89(10) . . ?
C13 C14 C22 132.29(11) . . ?
O2 C10 C11 115.78(10) . . ?
O2 C10 C9 123.84(11) . . ?
C11 C10 C9 120.37(10) . . ?
C5 C6 C1 120.41(12) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N1 C19 C17 178.29(12) . . ?
C17 C16 C15 116.26(10) . . ?
C17 C16 C7 124.61(10) . . ?
C15 C16 C7 118.92(9) . . ?
C3 C4 C5 119.41(11) . . ?
C3 C4 C18 122.06(10) . . ?
C5 C4 C18 118.49(11) . . ?
N2 C13 C21 120.48(10) . . ?
N2 C13 C14 110.37(10) . . ?
C14 C13 C21 129.12(10) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.07(12) . . ?
C1 C2 H2 120.0 . . ?

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 C18 C4 C3 -149.99(12) . . . . ?
O1 C18 C4 C5 27.54(17) . . . . ?
C11 C12 C7 C8 1.49(17) . . . . ?
C11 C12 C7 C16 -179.33(11) . . . . ?
N3 C15 C16 C17 -133.69(12) . . . . ?
N3 C15 C16 C7 51.32(16) . . . . ?
N3 C14 C13 C21 -179.18(12) . . . . ?
N3 C14 C13 N2 -1.24(13) . . . . ?
C20 O2 C10 C11 -174.85(11) . . . . ?
C20 O2 C10 C9 6.51(17) . . . . ?
N2 C15 C16 C17 39.95(16) . . . . ?
N2 C15 C16 C7 -135.05(12) . . . . ?
C17 C18 C4 C3 25.35(17) . . . . ?
C17 C18 C4 C5 -157.12(11) . . . . ?
C9 C8 C7 C12 -2.67(17) . . . . ?
C9 C8 C7 C16 178.13(11) . . . . ?
C12 C11 C10 O2 179.01(10) . . . . ?
C12 C11 C10 C9 -2.30(17) . . . . ?
C12 C7 C16 C17 37.75(17) . . . . ?
C12 C7 C16 C15 -147.70(11) . . . . ?
C18 C17 C16 C15 9.89(17) . . . . ?
C18 C17 C16 C7 -175.43(11) . . . . ?
C8 C9 C10 O2 179.72(11) . . . . ?
C8 C9 C10 C11 1.14(17) . . . . ?
C8 C7 C16 C17 -143.08(12) . . . . ?
C8 C7 C16 C15 31.47(15) . . . . ?
C15 N3 C14 C22 -175.97(11) . . . . ?
C15 N3 C14 C13 1.73(13) . . . . ?
C15 N2 C13 C21 178.37(11) . . . . ?
C15 N2 C13 C14 0.22(13) . . . . ?
C22 C14 C13 C21 -1.8(2) . . . . ?
C22 C14 C13 N2 176.12(12) . . . . ?
C23 N3 C15 N2 -175.10(11) . . . . ?
C23 N3 C15 C16 -0.87(19) . . . . ?
C23 N3 C14 C22 -2.22(18) . . . . ?
C23 N3 C14 C13 175.48(11) . . . . ?
C14 N3 C15 N2 -1.70(13) . . . . ?
C14 N3 C15 C16 172.53(11) . . . . ?
C10 C11 C12 C7 0.95(17) . . . . ?
C10 C9 C8 C7 1.36(17) . . . . ?
C6 C5 C4 C3 -1.10(19) . . . . ?
C6 C5 C4 C18 -178.70(12) . . . . ?
C6 C1 C2 C3 -0.3(2) . . . . ?
C19 C17 C18 O1 31.67(16) . . . . ?
C19 C17 C18 C4 -143.75(11) . . . . ?
C19 C17 C16 C15 -162.95(11) . . . . ?
C19 C17 C16 C7 11.73(18) . . . . ?
C16 C17 C18 O1 -141.66(13) . . . . ?
C16 C17 C18 C4 42.92(17) . . . . ?
C4 C3 C2 C1 0.50(19) . . . . ?
C4 C5 C6 C1 1.3(2) . . . . ?
C13 N2 C15 N3 0.92(13) . . . . ?
C13 N2 C15 C16 -173.52(10) . . . . ?
C2 C3 C4 C5 0.20(18) . . . . ?
C2 C3 C4 C18 177.71(11) . . . . ?
C2 C1 C6 C5 -0.6(2) . . . . ?

_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_mv1113
_database_code_depnum_ccdc_archive 'CCDC 2215935'
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.	2024-05-02 downloaded from the CCDC.
;
_audit_creation_date             2022-11-08
_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 H18 Cl2 N3 O2'
_chemical_formula_sum            'C22 H18 Cl2 N3 O2'
_chemical_formula_weight         427.29
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.8855(2)
_cell_length_b                   10.0424(2)
_cell_length_c                   29.2647(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4080.78(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9977
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.52
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.935
_exptl_absorpt_coefficient_mu    0.342
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1194 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.9047.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1768
_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  0.0526
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            52179
_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         28.994
_diffrn_reflns_theta_min         2.022
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4562
_reflns_number_total             5423
_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         0.621
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.058
_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     265
_refine_ls_number_reflns         5423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0354
_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)+(0.0434P)²+2.5820P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0951
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C9(H9), C3(H3), C2(H2), C8(H8), C6(H6), C11(H11)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_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
Cl2 Cl 0.48999(2) 0.71365(3) 0.50875(2) 0.01982(9) Uani 1 1 d . . . . .
C15 C 0.49100(9) 0.67869(13) 0.61263(5) 0.0126(2) Uani 1 1 d . . . . .
C1 C 0.39472(12) 0.14229(15) 0.77112(5) 0.0230(3) Uani 1 1 d . . . . .
H1 H 0.3912 0.0732 0.7932 0.028 Uiso 1 1 calc R U . . .
Cl1 Cl 0.14740(3) 0.51358(4) 0.45868(2) 0.02806(10) Uani 1 1 d . . . . .
O2 O 0.34052(7) 0.53629(9) 0.67198(3) 0.0152(2) Uani 1 1 d . . . . .
C20 C 0.40496(12) 0.99569(14) 0.65741(6) 0.0228(3) Uani 1 1 d . . . . .
H20A H 0.3594 1.0206 0.6333 0.034 Uiso 1 1 calc R U . . .
H20B H 0.4470 1.0715 0.6643 0.034 Uiso 1 1 calc R U . . .
H20C H 0.3693 0.9704 0.6850 0.034 Uiso 1 1 calc R U . . .
O1 O 0.32752(6) 0.73738(9) 0.62501(3) 0.01452(19) Uani 1 1 d . . . . .
C10 C 0.24193(11) 0.52080(14) 0.49746(5) 0.0184(3) Uani 1 1 d . . . . .
N1 N 0.42363(8) 0.76571(11) 0.62491(4) 0.0122(2) Uani 1 1 d . . . . .
C5 C 0.48847(11) 0.29774(14) 0.72715(5) 0.0185(3) Uani 1 1 d . . . . .
H5 H 0.5491 0.3356 0.7196 0.022 Uiso 1 1 calc R U . . .
N2 N 0.57623(8) 0.73560(11) 0.62194(4) 0.0144(2) Uani 1 1 d . . . . .
C22 C 0.66913(10) 0.67567(15) 0.61126(6) 0.0218(3) Uani 1 1 d . . . . .
H22A H 0.6824 0.6859 0.5786 0.033 Uiso 1 1 calc R U . . .
H22B H 0.6677 0.5808 0.6191 0.033 Uiso 1 1 calc R U . . .
H22C H 0.7197 0.7200 0.6290 0.033 Uiso 1 1 calc R U . . .
C19 C 0.40677(9) 0.44626(13) 0.66852(4) 0.0126(2) Uani 1 1 d . . . . .
N3 N 0.60450(10) 0.26372(14) 0.62429(5) 0.0287(3) Uani 1 1 d . . . . .
C13 C 0.46435(10) 0.88137(13) 0.64176(5) 0.0143(3) Uani 1 1 d . . . . .
C7 C 0.39192(10) 0.53400(13) 0.56054(4) 0.0131(2) Uani 1 1 d . . . . .
C16 C 0.47558(9) 0.54122(13) 0.59421(5) 0.0127(2) Uani 1 1 d . . . . .
H16 H 0.5347 0.5196 0.5761 0.015 Uiso 1 1 calc R U . . .
C9 C 0.23881(11) 0.44212(14) 0.53617(5) 0.0183(3) Uani 1 1 d . . . . .
H9 H 0.1859 0.3842 0.5414 0.022 Uiso 1 1 calc R U . . .
C3 C 0.31631(11) 0.28688(14) 0.71716(5) 0.0178(3) Uani 1 1 d . . . . .
H3 H 0.2591 0.3181 0.7030 0.021 Uiso 1 1 calc R U . . .
C14 C 0.56112(10) 0.86176(13) 0.64018(5) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.31138(12) 0.18677(15) 0.74979(5) 0.0221(3) Uani 1 1 d . . . . .
H2 H 0.2509 0.1487 0.7575 0.027 Uiso 1 1 calc R U . . .
C8 C 0.31410(10) 0.44893(13) 0.56730(5) 0.0155(3) Uani 1 1 d . . . . .
H8 H 0.3124 0.3943 0.5938 0.019 Uiso 1 1 calc R U . . .
C6 C 0.48289(12) 0.19836(15) 0.76023(5) 0.0227(3) Uani 1 1 d . . . . .
H6 H 0.5396 0.1690 0.7753 0.027 Uiso 1 1 calc R U . . .
C17 C 0.47250(9) 0.44036(13) 0.63313(5) 0.0132(2) Uani 1 1 d . . . . .
C21 C 0.64065(11) 0.94586(15) 0.65850(6) 0.0219(3) Uani 1 1 d . . . . .
H21A H 0.6607 0.9117 0.6884 0.033 Uiso 1 1 calc R U . . .
H21B H 0.6181 1.0379 0.6618 0.033 Uiso 1 1 calc R U . . .
H21C H 0.6954 0.9433 0.6374 0.033 Uiso 1 1 calc R U . . .
C4 C 0.40524(10) 0.34197(13) 0.70510(5) 0.0142(3) Uani 1 1 d . . . . .
C12 C 0.39299(10) 0.60903(13) 0.52050(5) 0.0148(3) Uani 1 1 d . . . . .
C11 C 0.31904(11) 0.60466(14) 0.48869(5) 0.0176(3) Uani 1 1 d . . . . .
H11 H 0.3212 0.6574 0.4618 0.021 Uiso 1 1 calc R U . . .
C18 C 0.54318(10) 0.33894(14) 0.62987(5) 0.0174(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 C12 1.7424(14) . ?
C15 N1 1.3296(17) . ?
C15 N2 1.3422(17) . ?
C15 C16 1.4974(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.389(2) . ?
C1 C6 1.385(2) . ?
Cl1 C10 1.7366(14) . ?
O2 C19 1.2938(16) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 C13 1.4859(19) . ?
O1 N1 1.3644(14) . ?
C10 C9 1.382(2) . ?
C10 C11 1.386(2) . ?
N1 C13 1.3829(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(2) . ?
C5 C4 1.3962(19) . ?
N2 C22 1.4573(18) . ?
N2 C14 1.3908(18) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C19 C17 1.3815(19) . ?
C19 C4 1.4978(18) . ?
N3 C18 1.1498(19) . ?
C13 C14 1.3588(19) . ?
C7 C16 1.5248(18) . ?
C7 C8 1.3917(19) . ?
C7 C12 1.3932(18) . ?
C16 H16 1.0000 . ?
C16 C17 1.5250(18) . ?
C9 H9 0.9500 . ?
C9 C8 1.3884(19) . ?
C3 H3 0.9500 . ?
C3 C2 1.388(2) . ?
C3 C4 1.398(2) . ?
C14 C21 1.4901(19) . ?
C2 H2 0.9500 . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
C17 C18 1.4177(18) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C12 C11 1.387(2) . ?
C11 H11 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C15 N2 106.60(11) . . ?
N1 C15 C16 127.06(12) . . ?
N2 C15 C16 126.28(12) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C6 C1 C2 120.17(14) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C20 H20A 109.5 . . ?
C13 C20 H20B 109.5 . . ?
C13 C20 H20C 109.5 . . ?
C9 C10 Cl1 119.22(12) . . ?
C9 C10 C11 121.56(13) . . ?
C11 C10 Cl1 119.22(11) . . ?
C15 N1 O1 123.48(11) . . ?
C15 N1 C13 111.15(11) . . ?
O1 N1 C13 125.05(11) . . ?
C6 C5 H5 119.9 . . ?
C6 C5 C4 120.22(14) . . ?
C4 C5 H5 119.9 . . ?
C15 N2 C22 124.13(12) . . ?
C15 N2 C14 109.44(11) . . ?
C14 N2 C22 126.31(12) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C19 C17 123.94(12) . . ?
O2 C19 C4 115.00(12) . . ?
C17 C19 C4 121.00(12) . . ?
N1 C13 C20 122.14(12) . . ?
C14 C13 C20 132.17(13) . . ?
C14 C13 N1 105.69(12) . . ?
C8 C7 C16 121.93(12) . . ?
C8 C7 C12 117.38(12) . . ?
C12 C7 C16 120.63(12) . . ?
C15 C16 C7 112.67(11) . . ?
C15 C16 H16 105.9 . . ?
C15 C16 C17 110.32(11) . . ?
C7 C16 H16 105.9 . . ?
C17 C16 C7 115.45(11) . . ?
C17 C16 H16 105.9 . . ?
C10 C9 H9 120.5 . . ?
C10 C9 C8 119.09(13) . . ?
C8 C9 H9 120.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.24(14) . . ?
C4 C3 H3 119.9 . . ?
N2 C14 C21 122.87(13) . . ?
C13 C14 N2 107.12(12) . . ?
C13 C14 C21 129.67(13) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.07(15) . . ?
C3 C2 H2 120.0 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.44(13) . . ?
C9 C8 H8 119.3 . . ?
C1 C6 C5 120.04(14) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C19 C17 C16 123.37(12) . . ?
C19 C17 C18 122.60(12) . . ?
C18 C17 C16 114.04(12) . . ?
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 . . ?
C5 C4 C19 122.76(12) . . ?
C5 C4 C3 119.24(13) . . ?
C3 C4 C19 118.01(12) . . ?
C7 C12 Cl2 120.03(11) . . ?
C11 C12 Cl2 117.32(11) . . ?
C11 C12 C7 122.66(13) . . ?
C10 C11 C12 117.83(13) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 H11 121.1 . . ?
N3 C18 C17 173.82(16) . . ?

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
Cl2 C12 C11 C10 179.38(11) . . . . ?
C15 N1 C13 C20 179.26(13) . . . . ?
C15 N1 C13 C14 -1.00(15) . . . . ?
C15 N2 C14 C13 -0.16(15) . . . . ?
C15 N2 C14 C21 173.69(13) . . . . ?
C15 C16 C17 C19 58.78(16) . . . . ?
C15 C16 C17 C18 -121.40(13) . . . . ?
Cl1 C10 C9 C8 -179.46(11) . . . . ?
Cl1 C10 C11 C12 179.46(11) . . . . ?
O2 C19 C17 C16 1.0(2) . . . . ?
O2 C19 C17 C18 -178.81(13) . . . . ?
O2 C19 C4 C5 -135.75(14) . . . . ?
O2 C19 C4 C3 44.61(17) . . . . ?
C20 C13 C14 N2 -179.62(14) . . . . ?
C20 C13 C14 C21 7.1(3) . . . . ?
O1 N1 C13 C20 -7.1(2) . . . . ?
O1 N1 C13 C14 172.64(11) . . . . ?
C10 C9 C8 C7 0.6(2) . . . . ?
N1 C15 N2 C22 -176.57(12) . . . . ?
N1 C15 N2 C14 -0.44(15) . . . . ?
N1 C15 C16 C7 40.21(18) . . . . ?
N1 C15 C16 C17 -90.43(16) . . . . ?
N1 C13 C14 N2 0.68(15) . . . . ?
N1 C13 C14 C21 -172.61(14) . . . . ?
N2 C15 N1 O1 -172.86(11) . . . . ?
N2 C15 N1 C13 0.90(15) . . . . ?
N2 C15 C16 C7 -143.13(13) . . . . ?
N2 C15 C16 C17 86.23(16) . . . . ?
C22 N2 C14 C13 175.86(13) . . . . ?
C22 N2 C14 C21 -10.3(2) . . . . ?
C7 C16 C17 C19 -70.37(16) . . . . ?
C7 C16 C17 C18 109.45(13) . . . . ?
C7 C12 C11 C10 -0.6(2) . . . . ?
C16 C15 N1 O1 4.3(2) . . . . ?
C16 C15 N1 C13 178.09(12) . . . . ?
C16 C15 N2 C22 6.2(2) . . . . ?
C16 C15 N2 C14 -177.67(12) . . . . ?
C16 C7 C8 C9 -179.29(12) . . . . ?
C16 C7 C12 Cl2 -0.63(17) . . . . ?
C16 C7 C12 C11 179.33(12) . . . . ?
C9 C10 C11 C12 -1.0(2) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
C2 C3 C4 C5 -1.8(2) . . . . ?
C2 C3 C4 C19 177.87(13) . . . . ?
C8 C7 C16 C15 -122.60(13) . . . . ?
C8 C7 C16 C17 5.40(18) . . . . ?
C8 C7 C12 Cl2 -177.88(10) . . . . ?
C8 C7 C12 C11 2.1(2) . . . . ?
C6 C1 C2 C3 0.6(2) . . . . ?
C6 C5 C4 C19 -178.59(13) . . . . ?
C6 C5 C4 C3 1.0(2) . . . . ?
C17 C19 C4 C5 46.88(19) . . . . ?
C17 C19 C4 C3 -132.76(14) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C4 C19 C17 C16 178.12(12) . . . . ?
C4 C19 C17 C18 -1.7(2) . . . . ?
C4 C3 C2 C1 1.0(2) . . . . ?
C12 C7 C16 C15 60.28(16) . . . . ?
C12 C7 C16 C17 -171.73(12) . . . . ?
C12 C7 C8 C9 -2.1(2) . . . . ?
C11 C10 C9 C8 1.0(2) . . . . ?

_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_mv1140
_database_code_depnum_ccdc_archive 'CCDC 2211260'
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.	2024-05-02 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         'C23 H21 N3 O S'
_chemical_formula_sum            'C23 H21 N3 O S'
_chemical_formula_weight         387.49
_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'
S S 0.1246 0.1234 '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                   13.4764(2)
_cell_length_b                   8.5980(2)
_cell_length_c                   17.6336(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.6100(10)
_cell_angle_gamma                90
_cell_volume                     2008.27(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9265
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.53
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_correction_T_min  0.5153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1822 before and 0.0972 after correction.
The Ratio of minimum to maximum transmission is 0.5977.
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    1.282
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            25188
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_min         2.561
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                4460
_reflns_number_total             5329
_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         0.392
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         5329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0478
_refine_ls_restrained_S_all      1.048
_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)+(0.0447P)²+1.0232P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1258
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C1(H1), C12(H12), C8(H8), C3(H3), C11(H11), C2(H2), C6(H6)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.81084(3) 0.72443(5) 0.59191(2) 0.02280(11) Uani 1 1 d . . . . .
C9 C 0.61373(11) 0.82280(17) 0.58989(8) 0.0180(3) Uani 1 1 d . . . . .
H9 H 0.6215 0.8948 0.5505 0.022 Uiso 1 1 calc R U . . .
C5 C 0.13313(12) 0.5960(2) 0.76426(9) 0.0243(3) Uani 1 1 d . . . . .
H5 H 0.1157 0.6792 0.7947 0.029 Uiso 1 1 calc R U . . .
O1 O 0.30313(9) 0.71297(14) 0.87329(6) 0.0259(3) Uani 1 1 d . . . . .
C23 C 0.33867(11) 0.57602(18) 0.54182(9) 0.0209(3) Uani 1 1 d . . . . .
H23A H 0.3599 0.6259 0.4975 0.031 Uiso 1 1 calc R U . . .
H23B H 0.2915 0.4914 0.5238 0.031 Uiso 1 1 calc R U . . .
H23C H 0.3979 0.5339 0.5764 0.031 Uiso 1 1 calc R U . . .
N3 N 0.28897(9) 0.69073(14) 0.58338(7) 0.0154(2) Uani 1 1 d . . . . .
C20 C 0.79941(13) 0.8821(2) 0.52388(10) 0.0305(4) Uani 1 1 d . . . . .
H20A H 0.7439 0.8606 0.4809 0.046 Uiso 1 1 calc R U . . .
H20B H 0.8625 0.8928 0.5042 0.046 Uiso 1 1 calc R U . . .
H20C H 0.7856 0.9788 0.5494 0.046 Uiso 1 1 calc R U . . .
N2 N 0.25388(9) 0.84563(14) 0.67658(7) 0.0158(2) Uani 1 1 d . . . . .
C10 C 0.69242(11) 0.72244(17) 0.61967(8) 0.0177(3) Uani 1 1 d . . . . .
N1 N 0.56858(11) 0.71264(17) 0.89007(8) 0.0268(3) Uani 1 1 d . . . . .
C21 C 0.07726(11) 0.92611(19) 0.62191(9) 0.0221(3) Uani 1 1 d . . . . .
H21A H 0.0320 0.8584 0.6446 0.033 Uiso 1 1 calc R U . . .
H21B H 0.0442 0.9571 0.5699 0.033 Uiso 1 1 calc R U . . .
H21C H 0.0931 1.0190 0.6541 0.033 Uiso 1 1 calc R U . . .
C16 C 0.41696(11) 0.71394(16) 0.70634(8) 0.0150(3) Uani 1 1 d . . . . .
C1 C 0.08342(13) 0.3823(2) 0.67818(10) 0.0323(4) Uani 1 1 d . . . . .
H1 H 0.0318 0.3202 0.6490 0.039 Uiso 1 1 calc R U . . .
C17 C 0.41084(11) 0.69021(17) 0.78208(8) 0.0164(3) Uani 1 1 d . . . . .
C15 C 0.32257(11) 0.75318(16) 0.65496(8) 0.0150(3) Uani 1 1 d . . . . .
C12 C 0.59040(11) 0.61097(17) 0.70492(8) 0.0175(3) Uani 1 1 d . . . . .
H12 H 0.5826 0.5384 0.7440 0.021 Uiso 1 1 calc R U . . .
C8 C 0.52408(11) 0.81755(17) 0.61778(8) 0.0168(3) Uani 1 1 d . . . . .
H8 H 0.4703 0.8850 0.5966 0.020 Uiso 1 1 calc R U . . .
C3 C 0.25905(11) 0.44116(18) 0.71895(8) 0.0197(3) Uani 1 1 d . . . . .
H3 H 0.3278 0.4201 0.7172 0.024 Uiso 1 1 calc R U . . .
C22 C 0.12698(12) 0.6944(2) 0.48615(9) 0.0243(3) Uani 1 1 d . . . . .
H22A H 0.1635 0.7098 0.4435 0.036 Uiso 1 1 calc R U . . .
H22B H 0.0650 0.7566 0.4771 0.036 Uiso 1 1 calc R U . . .
H22C H 0.1097 0.5841 0.4894 0.036 Uiso 1 1 calc R U . . .
C4 C 0.23424(11) 0.56446(17) 0.76294(8) 0.0172(3) Uani 1 1 d . . . . .
C11 C 0.67920(11) 0.61396(17) 0.67626(8) 0.0185(3) Uani 1 1 d . . . . .
H11 H 0.7315 0.5421 0.6950 0.022 Uiso 1 1 calc R U . . .
C14 C 0.19211(11) 0.74386(17) 0.55999(8) 0.0169(3) Uani 1 1 d . . . . .
C19 C 0.49890(11) 0.70183(17) 0.84170(8) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.18343(13) 0.3487(2) 0.67750(9) 0.0275(4) Uani 1 1 d . . . . .
H2 H 0.2005 0.2625 0.6487 0.033 Uiso 1 1 calc R U . . .
C7 C 0.51165(11) 0.71431(16) 0.67676(8) 0.0152(3) Uani 1 1 d . . . . .
C13 C 0.17241(11) 0.84054(17) 0.61761(8) 0.0169(3) Uani 1 1 d . . . . .
C18 C 0.31394(11) 0.66338(17) 0.81057(8) 0.0175(3) Uani 1 1 d . . . . .
C6 C 0.05808(12) 0.5056(2) 0.72108(10) 0.0317(4) Uani 1 1 d . . . . .
H6 H -0.0109 0.5286 0.7210 0.038 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
S1 C20 1.7977(18) . ?
S1 C10 1.7534(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.393(2) . ?
C9 C8 1.387(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.394(2) . ?
C5 C6 1.386(2) . ?
O1 C18 1.2187(18) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 N3 1.4625(19) . ?
N3 C15 1.3696(17) . ?
N3 C14 1.3728(18) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N2 C15 1.3282(19) . ?
N2 C13 1.3669(18) . ?
C10 C11 1.401(2) . ?
N1 C19 1.150(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 C13 1.492(2) . ?
C16 C17 1.3685(19) . ?
C16 C15 1.4588(19) . ?
C16 C7 1.465(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(3) . ?
C1 C6 1.382(3) . ?
C17 C19 1.437(2) . ?
C17 C18 1.501(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.382(2) . ?
C12 C7 1.403(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.401(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C3 C2 1.389(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 C14 1.492(2) . ?
C4 C18 1.500(2) . ?
C11 H11 0.9500 . ?
C14 C13 1.376(2) . ?
C2 H2 0.9500 . ?
C6 H6 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
C10 S1 C20 102.89(8) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.91(13) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 119.91(16) . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
C15 N3 C23 128.46(12) . . ?
C15 N3 C14 106.33(12) . . ?
C14 N3 C23 124.87(12) . . ?
S1 C20 H20A 109.5 . . ?
S1 C20 H20B 109.5 . . ?
S1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 N2 C13 105.49(12) . . ?
C9 C10 S1 123.89(12) . . ?
C9 C10 C11 119.55(14) . . ?
C11 C10 S1 116.55(11) . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
C17 C16 C15 116.00(13) . . ?
C17 C16 C7 124.11(13) . . ?
C15 C16 C7 119.70(12) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.36(16) . . ?
C6 C1 H1 119.8 . . ?
C16 C17 C19 120.91(13) . . ?
C16 C17 C18 124.20(13) . . ?
C19 C17 C18 114.72(12) . . ?
N3 C15 C16 125.74(13) . . ?
N2 C15 N3 111.69(12) . . ?
N2 C15 C16 122.29(13) . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C7 120.54(13) . . ?
C7 C12 H12 119.7 . . ?
C9 C8 H8 119.5 . . ?
C9 C8 C7 121.01(13) . . ?
C7 C8 H8 119.5 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.09(15) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C14 C22 H22A 109.5 . . ?
C14 C22 H22B 109.5 . . ?
C14 C22 H22C 109.5 . . ?
C5 C4 C18 118.81(14) . . ?
C3 C4 C5 119.59(14) . . ?
C3 C4 C18 121.59(13) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.33(14) . . ?
C12 C11 H11 119.8 . . ?
N3 C14 C22 122.77(14) . . ?
N3 C14 C13 106.34(12) . . ?
C13 C14 C22 130.87(14) . . ?
N1 C19 C17 178.93(18) . . ?
C1 C2 C3 119.90(17) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C12 C7 C16 121.63(13) . . ?
C8 C7 C16 119.79(13) . . ?
C8 C7 C12 118.56(13) . . ?
N2 C13 C21 121.52(13) . . ?
N2 C13 C14 110.12(13) . . ?
C14 C13 C21 128.30(13) . . ?
O1 C18 C17 120.44(13) . . ?
O1 C18 C4 120.90(14) . . ?
C4 C18 C17 118.50(12) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 C5 120.12(16) . . ?
C1 C6 H6 119.9 . . ?

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
S1 C10 C11 C12 176.00(11) . . . . ?
C9 C10 C11 C12 -2.9(2) . . . . ?
C9 C8 C7 C16 178.55(13) . . . . ?
C9 C8 C7 C12 -2.8(2) . . . . ?
C5 C4 C18 O1 35.6(2) . . . . ?
C5 C4 C18 C17 -148.91(14) . . . . ?
C23 N3 C15 N2 -175.35(13) . . . . ?
C23 N3 C15 C16 -1.4(2) . . . . ?
C23 N3 C14 C22 -2.8(2) . . . . ?
C23 N3 C14 C13 175.62(13) . . . . ?
N3 C14 C13 N2 -1.30(16) . . . . ?
N3 C14 C13 C21 -178.63(14) . . . . ?
C20 S1 C10 C9 1.62(15) . . . . ?
C20 S1 C10 C11 -177.21(12) . . . . ?
C10 C9 C8 C7 1.1(2) . . . . ?
C16 C17 C18 O1 -145.46(15) . . . . ?
C16 C17 C18 C4 39.0(2) . . . . ?
C17 C16 C15 N3 -134.99(15) . . . . ?
C17 C16 C15 N2 38.4(2) . . . . ?
C17 C16 C7 C12 37.9(2) . . . . ?
C17 C16 C7 C8 -143.48(15) . . . . ?
C15 N3 C14 C22 -176.51(14) . . . . ?
C15 N3 C14 C13 1.89(15) . . . . ?
C15 N2 C13 C21 177.69(13) . . . . ?
C15 N2 C13 C14 0.14(16) . . . . ?
C15 C16 C17 C19 -159.32(13) . . . . ?
C15 C16 C17 C18 15.7(2) . . . . ?
C15 C16 C7 C12 -147.35(14) . . . . ?
C15 C16 C7 C8 31.29(19) . . . . ?
C8 C9 C10 S1 -177.10(11) . . . . ?
C8 C9 C10 C11 1.7(2) . . . . ?
C3 C4 C18 O1 -143.20(15) . . . . ?
C3 C4 C18 C17 32.3(2) . . . . ?
C22 C14 C13 N2 176.93(15) . . . . ?
C22 C14 C13 C21 -0.4(3) . . . . ?
C4 C5 C6 C1 1.5(2) . . . . ?
C4 C3 C2 C1 1.9(2) . . . . ?
C11 C12 C7 C16 -179.77(13) . . . . ?
C11 C12 C7 C8 1.6(2) . . . . ?
C14 N3 C15 N2 -1.92(16) . . . . ?
C14 N3 C15 C16 172.06(13) . . . . ?
C19 C17 C18 O1 29.8(2) . . . . ?
C19 C17 C18 C4 -145.70(13) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
C2 C3 C4 C18 177.88(14) . . . . ?
C7 C16 C17 C19 15.6(2) . . . . ?
C7 C16 C17 C18 -169.39(13) . . . . ?
C7 C16 C15 N3 49.8(2) . . . . ?
C7 C16 C15 N2 -136.79(14) . . . . ?
C7 C12 C11 C10 1.2(2) . . . . ?
C13 N2 C15 N3 1.11(16) . . . . ?
C13 N2 C15 C16 -173.11(13) . . . . ?
C6 C5 C4 C3 -0.8(2) . . . . ?
C6 C5 C4 C18 -179.63(14) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mv1110
_database_code_depnum_ccdc_archive 'CCDC 2215936'
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             
;
2022-11-11 deposited with the CCDC.	2024-05-02 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 H21 N4 O3, C H4 O'
_chemical_formula_sum            'C26 H25 N4 O4'
_chemical_formula_weight         457.50
_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                   10.6494(3)
_cell_length_b                   10.3451(3)
_cell_length_c                   21.0786(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.4710(10)
_cell_angle_gamma                90
_cell_volume                     2296.88(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7139
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1018 before and 0.0480 after correction.
The Ratio of minimum to maximum transmission is 0.8821.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             964
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0538
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            29945
_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         1.954
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4573
_reflns_number_total             6100
_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         0.561
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         6100
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.053
_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)+(0.0512P)²+1.1162P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1324
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1S-C1S' \\sim O1S-C1S
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1S) = Uanis(C1S')
4. Others
 Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(H1SC)=1-FVAR(1)
 Sof(C1S')=Sof(H1SD)=Sof(H1SE)=Sof(H1SF)=FVAR(1)
5.a Riding coordinates:
 N3(H3), O1S(H1S)
5.b Ternary CH refined with riding coordinates:
 C19(H19)
5.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C6(H6), C2(H2), C11(H11), C5(H5), C1(H1), C15(H15),
 C3(H3A), C13(H13)
5.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C1S(H1SA,H1SB,
 H1SC), C1S'(H1SD,H1SE,H1SF)
;
_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 0.22647(11) 0.86276(11) 0.52248(6) 0.0250(3) Uani 1 1 d . . . . .
C25 C 0.4433(2) 1.10803(17) 0.71807(9) 0.0330(4) Uani 1 1 d . . . . .
H25A H 0.3517 1.1136 0.7191 0.049 Uiso 1 1 calc R U . . .
H25B H 0.4755 1.1932 0.7080 0.049 Uiso 1 1 calc R U . . .
H25C H 0.4864 1.0795 0.7600 0.049 Uiso 1 1 calc R U . . .
C10 C -0.13206(16) 0.60779(18) 0.53545(9) 0.0291(4) Uani 1 1 d . . . . .
H10 H -0.1816 0.6653 0.5068 0.035 Uiso 1 1 calc R U . . .
O2 O 0.44945(12) 0.67031(11) 0.73680(5) 0.0256(3) Uani 1 1 d . . . . .
O1 O 0.31902(11) 0.85363(11) 0.69735(6) 0.0248(3) Uani 1 1 d . . . . .
C12 C -0.11513(18) 0.41475(19) 0.60023(10) 0.0339(4) Uani 1 1 d . . . . .
H12 H -0.1541 0.3404 0.6152 0.041 Uiso 1 1 calc R U . . .
N2 N 0.53490(12) 0.89759(12) 0.59174(6) 0.0185(3) Uani 1 1 d . . . . .
N1 N 0.40512(13) 0.89686(13) 0.66030(6) 0.0208(3) Uani 1 1 d . . . . .
N3 N 0.05443(12) 0.74037(14) 0.53381(7) 0.0224(3) Uani 1 1 d . . . . .
H3 H 0.0036 0.7965 0.5102 0.027 Uiso 1 1 d R U . . .
C6 C 0.5998(2) 0.33345(19) 0.82520(9) 0.0360(4) Uani 1 1 d . . . . .
H6 H 0.5707 0.2972 0.8618 0.043 Uiso 1 1 calc R U . . .
N4 N 0.50954(14) 0.39034(14) 0.56503(7) 0.0268(3) Uani 1 1 d . . . . .
C18 C 0.44515(15) 0.82654(15) 0.61436(7) 0.0185(3) Uani 1 1 d . . . . .
C21 C 0.49879(15) 0.47708(15) 0.59831(8) 0.0196(3) Uani 1 1 d . . . . .
C8 C 0.18083(15) 0.76611(15) 0.54601(7) 0.0197(3) Uani 1 1 d . . . . .
C20 C 0.47509(14) 0.58826(15) 0.63430(7) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.75717(17) 0.34521(17) 0.75499(8) 0.0273(4) Uani 1 1 d . . . . .
H2 H 0.8354 0.3172 0.7430 0.033 Uiso 1 1 calc R U . . .
C19 C 0.40146(14) 0.69353(14) 0.59395(7) 0.0174(3) Uani 1 1 d . . . . .
H19 H 0.4233 0.6825 0.5497 0.021 Uiso 1 1 calc R U . . .
C11 C -0.18613(17) 0.4993(2) 0.55775(10) 0.0342(5) Uani 1 1 d . . . . .
H11 H -0.2734 0.4817 0.5439 0.041 Uiso 1 1 calc R U . . .
C7 C 0.25809(14) 0.67493(15) 0.58739(7) 0.0178(3) Uani 1 1 d . . . . .
C5 C 0.52843(19) 0.42757(18) 0.78984(9) 0.0307(4) Uani 1 1 d . . . . .
H5 H 0.4504 0.4554 0.8020 0.037 Uiso 1 1 calc R U . . .
C9 C -0.00295(15) 0.63234(16) 0.55552(8) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.71350(19) 0.29165(17) 0.80758(9) 0.0316(4) Uani 1 1 d . . . . .
H1 H 0.7614 0.2261 0.8317 0.038 Uiso 1 1 calc R U . . .
C15 C 0.20334(15) 0.57369(15) 0.61307(8) 0.0205(3) Uani 1 1 d . . . . .
H15 H 0.2545 0.5181 0.6420 0.025 Uiso 1 1 calc R U . . .
C22 C 0.49403(15) 0.58638(15) 0.70052(8) 0.0194(3) Uani 1 1 d . . . . .
C4 C 0.57104(15) 0.48153(15) 0.73634(7) 0.0208(3) Uani 1 1 d . . . . .
C14 C 0.07019(16) 0.54788(16) 0.59784(8) 0.0222(3) Uani 1 1 d . . . . .
C16 C 0.55078(16) 1.01382(15) 0.62507(8) 0.0217(3) Uani 1 1 d . . . . .
C17 C 0.46792(16) 1.01374(15) 0.66821(8) 0.0228(3) Uani 1 1 d . . . . .
C3 C 0.68586(16) 0.44053(16) 0.71960(8) 0.0228(3) Uani 1 1 d . . . . .
H3A H 0.7161 0.4779 0.6836 0.027 Uiso 1 1 calc R U . . .
C23 C 0.60643(16) 0.86059(16) 0.54041(8) 0.0234(3) Uani 1 1 d . . . . .
H23A H 0.6934 0.8375 0.5589 0.035 Uiso 1 1 calc R U . . .
H23B H 0.6084 0.9333 0.5108 0.035 Uiso 1 1 calc R U . . .
H23C H 0.5654 0.7862 0.5172 0.035 Uiso 1 1 calc R U . . .
C24 C 0.65129(18) 1.10903(16) 0.61528(9) 0.0277(4) Uani 1 1 d . . . . .
H24A H 0.7349 1.0728 0.6314 0.042 Uiso 1 1 calc R U . . .
H24B H 0.6387 1.1889 0.6386 0.042 Uiso 1 1 calc R U . . .
H24C H 0.6463 1.1281 0.5694 0.042 Uiso 1 1 calc R U . . .
C13 C 0.01140(17) 0.43902(17) 0.62049(9) 0.0285(4) Uani 1 1 d . . . . .
H13 H 0.0594 0.3819 0.6500 0.034 Uiso 1 1 calc R U . . .
O1S O 0.12380(13) 1.09869(14) 0.53479(7) 0.0398(4) Uani 1 1 d D . . . .
H1S H 0.1465 1.0223 0.5231 0.048 Uiso 1 1 d R U . A .
C1S C 0.1692(4) 1.1227(4) 0.59970(16) 0.0545(10) Uani 0.733(6) 1 d D . P A 1
H1SA H 0.1018 1.1626 0.6201 0.082 Uiso 0.733(6) 1 calc R U P A 1
H1SB H 0.2421 1.1813 0.6030 0.082 Uiso 0.733(6) 1 calc R U P A 1
H1SC H 0.1952 1.0411 0.6213 0.082 Uiso 0.733(6) 1 calc R U P A 1
C1S' C 0.0936(12) 1.0779(10) 0.5952(4) 0.0545(10) Uani 0.267(6) 1 d D . P A 2
H1SD H 0.1412 1.0032 0.6147 0.082 Uiso 0.267(6) 1 calc R U P A 2
H1SE H 0.0023 1.0610 0.5922 0.082 Uiso 0.267(6) 1 calc R U P A 2
H1SF H 0.1157 1.1546 0.6218 0.082 Uiso 0.267(6) 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
O3 C8 1.2461(19) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C25 C17 1.485(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(3) . ?
C10 C9 1.401(2) . ?
O2 C22 1.2927(19) . ?
O1 N1 1.3644(17) . ?
C12 H12 0.9500 . ?
C12 C11 1.392(3) . ?
C12 C13 1.375(3) . ?
N2 C18 1.347(2) . ?
N2 C16 1.390(2) . ?
N2 C23 1.463(2) . ?
N1 C18 1.331(2) . ?
N1 C17 1.380(2) . ?
N3 H3 0.8937 . ?
N3 C8 1.359(2) . ?
N3 C9 1.383(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.384(3) . ?
C6 C1 1.387(3) . ?
N4 C21 1.155(2) . ?
C18 C19 1.495(2) . ?
C21 C20 1.421(2) . ?
C8 C7 1.455(2) . ?
C20 C19 1.526(2) . ?
C20 C22 1.381(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.380(3) . ?
C2 C3 1.392(2) . ?
C19 H19 1.0000 . ?
C19 C7 1.525(2) . ?
C11 H11 0.9500 . ?
C7 C15 1.350(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.393(2) . ?
C9 C14 1.400(2) . ?
C1 H1 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.432(2) . ?
C22 C4 1.496(2) . ?
C4 C3 1.388(2) . ?
C14 C13 1.406(2) . ?
C16 C17 1.357(2) . ?
C16 C24 1.491(2) . ?
C3 H3A 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C13 H13 0.9500 . ?
O1S H1S 0.8723 . ?
O1S C1S 1.404(4) . ?
O1S C1S' 1.376(10) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C1S' H1SD 0.9800 . ?
C1S' H1SE 0.9800 . ?
C1S' H1SF 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
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C17 C25 H25A 109.5 . . ?
C17 C25 H25B 109.5 . . ?
C17 C25 H25C 109.5 . . ?
C11 C10 H10 120.4 . . ?
C11 C10 C9 119.10(18) . . ?
C9 C10 H10 120.4 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 119.96(18) . . ?
C18 N2 C16 109.44(13) . . ?
C18 N2 C23 126.36(13) . . ?
C16 N2 C23 124.21(14) . . ?
O1 N1 C17 124.93(13) . . ?
C18 N1 O1 123.49(13) . . ?
C18 N1 C17 111.44(14) . . ?
C8 N3 H3 118.6 . . ?
C8 N3 C9 124.69(14) . . ?
C9 N3 H3 116.7 . . ?
C5 C6 H6 119.8 . . ?
C5 C6 C1 120.47(17) . . ?
C1 C6 H6 119.8 . . ?
N2 C18 C19 127.38(14) . . ?
N1 C18 N2 106.22(13) . . ?
N1 C18 C19 126.37(14) . . ?
N4 C21 C20 174.01(17) . . ?
O3 C8 N3 121.03(15) . . ?
O3 C8 C7 122.66(14) . . ?
N3 C8 C7 116.31(14) . . ?
C21 C20 C19 113.40(13) . . ?
C22 C20 C21 121.17(14) . . ?
C22 C20 C19 124.07(14) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.54(17) . . ?
C3 C2 H2 120.2 . . ?
C18 C19 C20 112.58(12) . . ?
C18 C19 H19 105.5 . . ?
C18 C19 C7 114.03(13) . . ?
C20 C19 H19 105.5 . . ?
C7 C19 C20 112.70(13) . . ?
C7 C19 H19 105.5 . . ?
C10 C11 C12 121.15(17) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C8 C7 C19 116.29(13) . . ?
C15 C7 C8 120.26(14) . . ?
C15 C7 C19 123.18(14) . . ?
C6 C5 H5 120.0 . . ?
C6 C5 C4 119.97(18) . . ?
C4 C5 H5 120.0 . . ?
N3 C9 C10 120.55(16) . . ?
N3 C9 C14 118.90(15) . . ?
C14 C9 C10 120.55(17) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 C6 120.05(16) . . ?
C2 C1 H1 120.0 . . ?
C7 C15 H15 119.1 . . ?
C7 C15 C14 121.77(15) . . ?
C14 C15 H15 119.1 . . ?
O2 C22 C20 125.23(14) . . ?
O2 C22 C4 114.23(13) . . ?
C20 C22 C4 120.54(14) . . ?
C5 C4 C22 118.66(15) . . ?
C3 C4 C5 119.19(15) . . ?
C3 C4 C22 122.10(14) . . ?
C9 C14 C15 117.77(15) . . ?
C9 C14 C13 118.84(16) . . ?
C13 C14 C15 123.29(16) . . ?
N2 C16 C24 122.53(15) . . ?
C17 C16 N2 107.18(14) . . ?
C17 C16 C24 130.08(15) . . ?
N1 C17 C25 121.87(16) . . ?
C16 C17 C25 132.36(16) . . ?
C16 C17 N1 105.72(14) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.76(16) . . ?
C4 C3 H3A 119.6 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C24 H24A 109.5 . . ?
C16 C24 H24B 109.5 . . ?
C16 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C12 C13 C14 120.38(18) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C1S O1S H1S 111.4 . . ?
C1S' O1S H1S 103.4 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
O1S C1S' H1SD 109.5 . . ?
O1S C1S' H1SE 109.5 . . ?
O1S C1S' H1SF 109.5 . . ?
H1SD C1S' H1SE 109.5 . . ?
H1SD C1S' H1SF 109.5 . . ?
H1SE C1S' H1SF 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C8 C7 C19 -7.6(2) . . . . ?
O3 C8 C7 C15 178.16(15) . . . . ?
C10 C9 C14 C15 175.85(15) . . . . ?
C10 C9 C14 C13 -0.8(2) . . . . ?
O2 C22 C4 C5 41.6(2) . . . . ?
O2 C22 C4 C3 -135.57(16) . . . . ?
O1 N1 C18 N2 -175.95(13) . . . . ?
O1 N1 C18 C19 2.2(2) . . . . ?
O1 N1 C17 C25 -2.2(2) . . . . ?
O1 N1 C17 C16 175.43(14) . . . . ?
N2 C18 C19 C20 91.61(18) . . . . ?
N2 C18 C19 C7 -138.38(16) . . . . ?
N2 C16 C17 C25 177.91(18) . . . . ?
N2 C16 C17 N1 0.64(17) . . . . ?
N1 C18 C19 C20 -86.17(19) . . . . ?
N1 C18 C19 C7 43.8(2) . . . . ?
N3 C8 C7 C19 172.17(13) . . . . ?
N3 C8 C7 C15 -2.0(2) . . . . ?
N3 C9 C14 C15 -4.1(2) . . . . ?
N3 C9 C14 C13 179.21(14) . . . . ?
C6 C5 C4 C22 -177.85(17) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
C18 N2 C16 C17 -0.72(18) . . . . ?
C18 N2 C16 C24 174.53(15) . . . . ?
C18 N1 C17 C25 -177.98(15) . . . . ?
C18 N1 C17 C16 -0.36(19) . . . . ?
C18 C19 C7 C8 54.11(18) . . . . ?
C18 C19 C7 C15 -131.86(16) . . . . ?
C21 C20 C19 C18 -142.67(14) . . . . ?
C21 C20 C19 C7 86.64(16) . . . . ?
C21 C20 C22 O2 -163.66(15) . . . . ?
C21 C20 C22 C4 16.2(2) . . . . ?
C8 N3 C9 C10 -173.87(15) . . . . ?
C8 N3 C9 C14 6.1(2) . . . . ?
C8 C7 C15 C14 3.8(2) . . . . ?
C20 C19 C7 C8 -175.93(13) . . . . ?
C20 C19 C7 C15 -1.9(2) . . . . ?
C20 C22 C4 C5 -138.26(17) . . . . ?
C20 C22 C4 C3 44.6(2) . . . . ?
C19 C20 C22 O2 2.1(3) . . . . ?
C19 C20 C22 C4 -178.04(14) . . . . ?
C19 C7 C15 C14 -170.05(14) . . . . ?
C11 C10 C9 N3 179.78(15) . . . . ?
C11 C10 C9 C14 -0.2(2) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C7 C15 C14 C9 -0.6(2) . . . . ?
C7 C15 C14 C13 175.90(15) . . . . ?
C5 C6 C1 C2 0.9(3) . . . . ?
C5 C4 C3 C2 1.0(2) . . . . ?
C9 C10 C11 C12 0.7(3) . . . . ?
C9 N3 C8 O3 176.86(14) . . . . ?
C9 N3 C8 C7 -2.9(2) . . . . ?
C9 C14 C13 C12 1.4(2) . . . . ?
C1 C6 C5 C4 -0.4(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C15 C14 C13 C12 -175.11(16) . . . . ?
C22 C20 C19 C18 50.6(2) . . . . ?
C22 C20 C19 C7 -80.12(18) . . . . ?
C22 C4 C3 C2 178.16(15) . . . . ?
C16 N2 C18 N1 0.49(17) . . . . ?
C16 N2 C18 C19 -177.65(14) . . . . ?
C17 N1 C18 N2 -0.08(18) . . . . ?
C17 N1 C18 C19 178.08(14) . . . . ?
C3 C2 C1 C6 -0.5(3) . . . . ?
C23 N2 C18 N1 -179.77(14) . . . . ?
C23 N2 C18 C19 2.1(2) . . . . ?
C23 N2 C16 C17 179.53(14) . . . . ?
C23 N2 C16 C24 -5.2(2) . . . . ?
C24 C16 C17 C25 3.1(3) . . . . ?
C24 C16 C17 N1 -174.12(16) . . . . ?
C13 C12 C11 C10 -0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
