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

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

data_mo_20220424lwx_201321_hly_674_zcs_0m_sq
_database_code_depnum_ccdc_archive 'CCDC 2190754'
loop_
_audit_author_name
_audit_author_address
'Ya-nan tyntianyanan'
;Guilin University of Technology
China
;
_audit_update_record             
;
2022-07-16 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_audit_creation_date             2022-07-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C22 H21 N)'
_chemical_formula_sum            'C88 H84 N4'
_chemical_formula_weight         1197.59
_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'

_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                   8.4028(5)
_cell_length_b                   11.9177(8)
_cell_length_c                   18.7199(11)
_cell_angle_alpha                78.497(3)
_cell_angle_beta                 86.338(2)
_cell_angle_gamma                74.483(2)
_cell_volume                     1769.93(19)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    6407
_cell_measurement_temperature    193.00
_cell_measurement_theta_max      27.463
_cell_measurement_theta_min      2.515
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1511 before and 0.0704 after correction.
The Ratio of minimum to maximum transmission is 0.9520.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.124
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            38325
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.466
_diffrn_reflns_theta_min         1.932
_diffrn_ambient_temperature      193.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5927
_reflns_number_total             8076
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         8076
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.049
_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)+(0.0681P)²+0.3281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1403
_refine_special_details          SQUEEZE
_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. Restrained distances
 C12-H12A \\sim C12-H12D
 with sigma of 0.02
 C12-H12B \\sim C12-H12E
 with sigma of 0.02
 C12-H12C \\sim C12-H12F
 with sigma of 0.02
3. Others
 Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C18(H18), C43(H43), C3(H3), C21(H21), C25(H25), C7(H7), C32(H32),
 C20(H20), C13(H13), C40(H40), C35(H35), C6(H6), C29(H29), C42(H42), C19(H19),
 C41(H41), C28(H28)
4.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C23(H23A,H23B,H23C), C15(H15A,H15B,H15C), C37(H37A,H37B,
 H37C), C12(H12A,H12B,H12C), C27(H27A,H27B,H27C), C5(H5A,H5B,H5C), C34(H34A,
 H34B,H34C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.00947(15) 0.57258(10) 0.26821(7) 0.0245(3) Uani 1 1 d . . . . .
N1 N 0.45194(15) 0.74134(10) 0.23520(6) 0.0229(3) Uani 1 1 d . . . . .
C22 C 0.40072(17) 0.74990(12) 0.16202(8) 0.0222(3) Uani 1 1 d . . . . .
C17 C 0.46195(17) 0.82363(12) 0.10439(8) 0.0229(3) Uani 1 1 d . . . . .
C38 C 0.26653(17) 0.38466(12) 0.22420(8) 0.0244(3) Uani 1 1 d . . . . .
C39 C 0.10085(17) 0.42515(13) 0.18984(8) 0.0244(3) Uani 1 1 d . . . . .
C14 C 0.73445(18) 0.87607(12) 0.07195(8) 0.0261(3) Uani 1 1 d . . . . .
C16 C 0.59177(17) 0.88177(12) 0.11714(8) 0.0228(3) Uani 1 1 d . . . . .
C9 C 0.57367(17) 0.94401(12) 0.17484(8) 0.0239(3) Uani 1 1 d . . . . .
C2 C 0.38097(17) 0.84991(12) 0.26076(7) 0.0226(3) Uani 1 1 d . . . . .
C44 C -0.02032(17) 0.52203(12) 0.20838(8) 0.0239(3) Uani 1 1 d . . . . .
C24 C 0.00706(18) 0.49252(13) 0.33609(8) 0.0244(3) Uani 1 1 d . . . . .
C31 C 0.28141(18) 0.36507(12) 0.30045(8) 0.0243(3) Uani 1 1 d . . . . .
C8 C 0.43114(17) 0.95166(12) 0.22690(8) 0.0235(3) Uani 1 1 d . . . . .
C30 C 0.13579(18) 0.38755(13) 0.35005(8) 0.0254(3) Uani 1 1 d . . . . .
C10 C 0.69454(18) 0.99980(13) 0.18628(8) 0.0270(3) Uani 1 1 d . . . . .
H10 H 0.679314 1.043351 0.224630 0.032 Uiso 1 1 calc R U . . .
C18 C 0.39913(18) 0.83882(13) 0.03473(8) 0.0273(3) Uani 1 1 d . . . . .
H18 H 0.434189 0.891361 -0.004349 0.033 Uiso 1 1 calc R U . . .
C11 C 0.83617(18) 0.99299(13) 0.14289(9) 0.0287(3) Uani 1 1 d . . . . .
C43 C -0.16758(19) 0.56677(14) 0.16959(8) 0.0297(3) Uani 1 1 d . . . . .
H43 H -0.247512 0.634016 0.181127 0.036 Uiso 1 1 calc R U . . .
C3 C 0.26684(19) 0.85670(13) 0.31838(8) 0.0281(3) Uani 1 1 d . . . . .
H3 H 0.236841 0.787037 0.342291 0.034 Uiso 1 1 calc R U . . .
C21 C 0.28973(18) 0.68873(13) 0.14807(8) 0.0273(3) Uani 1 1 d . . . . .
H21 H 0.251662 0.637320 0.186848 0.033 Uiso 1 1 calc R U . . .
C25 C -0.11779(18) 0.51601(14) 0.38844(8) 0.0291(3) Uani 1 1 d . . . . .
H25 H -0.202229 0.588143 0.379155 0.035 Uiso 1 1 calc R U . . .
C7 C 0.35531(19) 1.05885(13) 0.24907(9) 0.0288(3) Uani 1 1 d . . . . .
H7 H 0.384559 1.128964 0.225478 0.035 Uiso 1 1 calc R U . . .
C32 C 0.43795(19) 0.32326(13) 0.33186(9) 0.0311(3) Uani 1 1 d . . . . .
H32 H 0.446731 0.309343 0.383400 0.037 Uiso 1 1 calc R U . . .
C20 C 0.23455(19) 0.70260(14) 0.07776(9) 0.0316(3) Uani 1 1 d . . . . .
H20 H 0.160608 0.659445 0.068365 0.038 Uiso 1 1 calc R U . . .
C36 C 0.41224(19) 0.36403(13) 0.18072(9) 0.0292(3) Uani 1 1 d . . . . .
C1 C 0.4446(2) 0.63182(13) 0.28619(8) 0.0299(3) Uani 1 1 d . . . . .
H1A H 0.329211 0.629056 0.294184 0.045 Uiso 1 1 calc R U . . .
H1B H 0.493223 0.630232 0.332714 0.045 Uiso 1 1 calc R U . . .
H1C H 0.506518 0.563105 0.265694 0.045 Uiso 1 1 calc R U . . .
C13 C 0.85319(18) 0.93053(13) 0.08640(8) 0.0285(3) Uani 1 1 d . . . . .
H13 H 0.949583 0.924731 0.056460 0.034 Uiso 1 1 calc R U . . .
C40 C 0.0631(2) 0.36986(15) 0.13624(9) 0.0319(3) Uani 1 1 d . . . . .
H40 H 0.140117 0.300734 0.125461 0.038 Uiso 1 1 calc R U . . .
C35 C 0.56463(19) 0.32295(14) 0.21487(10) 0.0341(4) Uani 1 1 d . . . . .
H35 H 0.661691 0.309015 0.185458 0.041 Uiso 1 1 calc R U . . .
C4 C 0.1958(2) 0.96375(14) 0.34166(9) 0.0318(3) Uani 1 1 d . . . . .
C6 C 0.2379(2) 1.06497(14) 0.30495(9) 0.0326(4) Uani 1 1 d . . . . .
H6 H 0.186101 1.139325 0.318107 0.039 Uiso 1 1 calc R U . . .
C29 C 0.1293(2) 0.30865(14) 0.41566(8) 0.0326(4) Uani 1 1 d . . . . .
H29 H 0.213792 0.236690 0.425807 0.039 Uiso 1 1 calc R U . . .
C33 C 0.58122(19) 0.30153(14) 0.28954(10) 0.0349(4) Uani 1 1 d . . . . .
C42 C -0.1975(2) 0.51327(15) 0.11426(9) 0.0355(4) Uani 1 1 d . . . . .
H42 H -0.296453 0.545314 0.087098 0.043 Uiso 1 1 calc R U . . .
C23 C -0.0804(2) 0.69700(13) 0.26680(9) 0.0329(4) Uani 1 1 d . . . . .
H23A H -0.060035 0.745348 0.220021 0.049 Uiso 1 1 calc R U . . .
H23B H -0.042112 0.725360 0.306546 0.049 Uiso 1 1 calc R U . . .
H23C H -0.198973 0.703300 0.272884 0.049 Uiso 1 1 calc R U . . .
C26 C -0.1218(2) 0.43678(16) 0.45367(9) 0.0344(4) Uani 1 1 d . . . . .
C19 C 0.28690(19) 0.77902(14) 0.02137(9) 0.0312(3) Uani 1 1 d . . . . .
H19 H 0.246066 0.790548 -0.026438 0.037 Uiso 1 1 calc R U . . .
C41 C -0.0839(2) 0.41364(16) 0.09857(9) 0.0364(4) Uani 1 1 d . . . . .
H41 H -0.106532 0.375218 0.062010 0.044 Uiso 1 1 calc R U . . .
C15 C 0.7676(2) 0.81241(15) 0.00809(9) 0.0340(4) Uani 1 1 d . . . . .
H15A H 0.722638 0.742917 0.018954 0.051 Uiso 1 1 calc R U . . .
H15B H 0.886970 0.786894 -0.000526 0.051 Uiso 1 1 calc R U . . .
H15C H 0.714643 0.866184 -0.035522 0.051 Uiso 1 1 calc R U . . .
C28 C 0.0033(2) 0.33221(16) 0.46628(9) 0.0371(4) Uani 1 1 d . . . . .
H28 H 0.002526 0.276217 0.510137 0.045 Uiso 1 1 calc R U . . .
C37 C 0.4131(2) 0.38682(17) 0.09826(9) 0.0400(4) Uani 1 1 d . . . . .
H37A H 0.417695 0.313110 0.081578 0.060 Uiso 1 1 calc R U . . .
H37B H 0.509865 0.415121 0.079568 0.060 Uiso 1 1 calc R U . . .
H37C H 0.312345 0.446995 0.080207 0.060 Uiso 1 1 calc R U . . .
C12 C 0.9699(2) 1.04781(17) 0.15792(11) 0.0402(4) Uani 1 1 d D . . . .
H12A H 1.023450 1.074139 0.111924 0.060 Uiso 0.53(3) 1 calc DR U P A 1
H12B H 1.052054 0.988940 0.190286 0.060 Uiso 0.53(3) 1 calc DR U P A 1
H12C H 0.921172 1.115974 0.181316 0.060 Uiso 0.53(3) 1 calc DR U P A 1
C27 C -0.2594(2) 0.4631(2) 0.50877(10) 0.0487(5) Uani 1 1 d . . . . .
H27A H -0.323743 0.404336 0.513792 0.073 Uiso 1 1 calc R U . . .
H27B H -0.331565 0.542560 0.492247 0.073 Uiso 1 1 calc R U . . .
H27C H -0.212278 0.459356 0.555995 0.073 Uiso 1 1 calc R U . . .
C5 C 0.0773(3) 0.96728(18) 0.40573(11) 0.0508(5) Uani 1 1 d . . . . .
H5A H 0.041486 1.048235 0.415322 0.076 Uiso 1 1 calc R U . . .
H5B H 0.132497 0.913447 0.448851 0.076 Uiso 1 1 calc R U . . .
H5C H -0.019072 0.942458 0.394639 0.076 Uiso 1 1 calc R U . . .
C34 C 0.7500(2) 0.25980(19) 0.32426(13) 0.0538(5) Uani 1 1 d . . . . .
H34A H 0.811484 0.185817 0.309218 0.081 Uiso 1 1 calc R U . . .
H34B H 0.737252 0.246102 0.377448 0.081 Uiso 1 1 calc R U . . .
H34C H 0.810479 0.320483 0.308582 0.081 Uiso 1 1 calc R U . . .
H12D H 0.952(5) 1.129(2) 0.130(2) 0.038(12) Uiso 0.47(3) 1 d D . P A 2
H12E H 1.080(3) 1.009(4) 0.139(2) 0.033(11) Uiso 0.47(3) 1 d D . P A 2
H12F H 0.981(6) 1.037(4) 0.2099(11) 0.041(13) Uiso 0.47(3) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C44 1.4372(18) . ?
N2 C24 1.4315(19) . ?
N2 C23 1.4687(18) . ?
N1 C22 1.4383(18) . ?
N1 C2 1.4339(17) . ?
N1 C1 1.4687(18) . ?
C22 C17 1.412(2) . ?
C22 C21 1.393(2) . ?
C17 C16 1.494(2) . ?
C17 C18 1.398(2) . ?
C38 C39 1.489(2) . ?
C38 C31 1.408(2) . ?
C38 C36 1.419(2) . ?
C39 C44 1.406(2) . ?
C39 C40 1.399(2) . ?
C14 C16 1.417(2) . ?
C14 C13 1.393(2) . ?
C14 C15 1.513(2) . ?
C16 C9 1.406(2) . ?
C9 C8 1.4901(19) . ?
C9 C10 1.402(2) . ?
C2 C8 1.408(2) . ?
C2 C3 1.397(2) . ?
C44 C43 1.396(2) . ?
C24 C30 1.409(2) . ?
C24 C25 1.400(2) . ?
C31 C30 1.487(2) . ?
C31 C32 1.398(2) . ?
C8 C7 1.397(2) . ?
C30 C29 1.398(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(2) . ?
C11 C13 1.389(2) . ?
C11 C12 1.509(2) . ?
C43 H43 0.9500 . ?
C43 C42 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.387(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.391(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.390(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.392(2) . ?
C20 H20 0.9500 . ?
C20 C19 1.382(2) . ?
C36 C35 1.390(2) . ?
C36 C37 1.513(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C13 H13 0.9500 . ?
C40 H40 0.9500 . ?
C40 C41 1.384(2) . ?
C35 H35 0.9500 . ?
C35 C33 1.379(2) . ?
C4 C6 1.386(2) . ?
C4 C5 1.509(2) . ?
C6 H6 0.9500 . ?
C29 H29 0.9500 . ?
C29 C28 1.384(2) . ?
C33 C34 1.514(2) . ?
C42 H42 0.9500 . ?
C42 C41 1.380(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C26 C28 1.388(2) . ?
C26 C27 1.511(2) . ?
C19 H19 0.9500 . ?
C41 H41 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C28 H28 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 H12D 0.978(19) . ?
C12 H12E 0.990(18) . ?
C12 H12F 0.963(19) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 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
C44 N2 C23 116.02(12) . . ?
C24 N2 C44 110.92(11) . . ?
C24 N2 C23 116.21(12) . . ?
C22 N1 C1 115.53(11) . . ?
C2 N1 C22 110.94(11) . . ?
C2 N1 C1 116.05(11) . . ?
C17 C22 N1 118.91(12) . . ?
C21 C22 N1 120.80(13) . . ?
C21 C22 C17 120.28(13) . . ?
C22 C17 C16 121.12(13) . . ?
C18 C17 C22 117.82(13) . . ?
C18 C17 C16 121.05(13) . . ?
C31 C38 C39 120.59(13) . . ?
C31 C38 C36 118.81(13) . . ?
C36 C38 C39 120.59(13) . . ?
C44 C39 C38 121.27(13) . . ?
C40 C39 C38 120.71(13) . . ?
C40 C39 C44 117.99(14) . . ?
C16 C14 C15 123.59(14) . . ?
C13 C14 C16 119.33(14) . . ?
C13 C14 C15 117.07(14) . . ?
C14 C16 C17 121.33(13) . . ?
C9 C16 C17 120.04(12) . . ?
C9 C16 C14 118.62(13) . . ?
C16 C9 C8 122.72(13) . . ?
C10 C9 C16 120.05(13) . . ?
C10 C9 C8 117.22(13) . . ?
C8 C2 N1 118.26(12) . . ?
C3 C2 N1 122.07(13) . . ?
C3 C2 C8 119.66(13) . . ?
C39 C44 N2 118.86(12) . . ?
C43 C44 N2 121.00(13) . . ?
C43 C44 C39 120.13(13) . . ?
C30 C24 N2 118.27(13) . . ?
C25 C24 N2 122.06(13) . . ?
C25 C24 C30 119.67(14) . . ?
C38 C31 C30 122.49(13) . . ?
C32 C31 C38 119.75(14) . . ?
C32 C31 C30 117.77(13) . . ?
C2 C8 C9 121.35(12) . . ?
C7 C8 C9 120.08(13) . . ?
C7 C8 C2 118.23(13) . . ?
C24 C30 C31 121.78(13) . . ?
C29 C30 C24 117.60(14) . . ?
C29 C30 C31 120.41(13) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.65(14) . . ?
C11 C10 H10 119.2 . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.53(14) . . ?
C19 C18 H18 119.2 . . ?
C10 C11 C12 121.38(15) . . ?
C13 C11 C10 117.74(14) . . ?
C13 C11 C12 120.85(15) . . ?
C44 C43 H43 119.9 . . ?
C42 C43 C44 120.18(14) . . ?
C42 C43 H43 119.9 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.47(14) . . ?
C4 C3 H3 119.3 . . ?
C22 C21 H21 119.9 . . ?
C20 C21 C22 120.25(14) . . ?
C20 C21 H21 119.9 . . ?
C24 C25 H25 119.0 . . ?
C26 C25 C24 121.91(15) . . ?
C26 C25 H25 119.0 . . ?
C8 C7 H7 119.3 . . ?
C6 C7 C8 121.33(14) . . ?
C6 C7 H7 119.3 . . ?
C31 C32 H32 119.2 . . ?
C33 C32 C31 121.68(15) . . ?
C33 C32 H32 119.2 . . ?
C21 C20 H20 119.9 . . ?
C19 C20 C21 120.16(14) . . ?
C19 C20 H20 119.9 . . ?
C38 C36 C37 123.90(14) . . ?
C35 C36 C38 118.96(15) . . ?
C35 C36 C37 117.12(14) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C14 C13 H13 118.7 . . ?
C11 C13 C14 122.58(14) . . ?
C11 C13 H13 118.7 . . ?
C39 C40 H40 119.3 . . ?
C41 C40 C39 121.46(15) . . ?
C41 C40 H40 119.3 . . ?
C36 C35 H35 118.5 . . ?
C33 C35 C36 122.93(15) . . ?
C33 C35 H35 118.5 . . ?
C3 C4 C5 120.15(15) . . ?
C6 C4 C3 118.42(14) . . ?
C6 C4 C5 121.42(14) . . ?
C7 C6 H6 119.7 . . ?
C4 C6 C7 120.69(14) . . ?
C4 C6 H6 119.7 . . ?
C30 C29 H29 119.0 . . ?
C28 C29 C30 121.99(15) . . ?
C28 C29 H29 119.0 . . ?
C32 C33 C34 121.02(17) . . ?
C35 C33 C32 117.85(15) . . ?
C35 C33 C34 121.09(16) . . ?
C43 C42 H42 119.9 . . ?
C41 C42 C43 120.18(15) . . ?
C41 C42 H42 119.9 . . ?
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 . . ?
C25 C26 C27 120.96(16) . . ?
C28 C26 C25 118.08(15) . . ?
C28 C26 C27 120.96(16) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.83(14) . . ?
C20 C19 H19 120.1 . . ?
C40 C41 H41 120.1 . . ?
C42 C41 C40 119.81(15) . . ?
C42 C41 H41 120.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C29 C28 C26 120.71(15) . . ?
C29 C28 H28 119.6 . . ?
C26 C28 H28 119.6 . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
C11 C12 H12D 111(2) . . ?
C11 C12 H12E 113(2) . . ?
C11 C12 H12F 108(2) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H12D C12 H12E 101(3) . . ?
H12D C12 H12F 117(3) . . ?
H12E C12 H12F 106(3) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 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
N2 C44 C43 C42 -176.92(14) . . . . ?
N2 C24 C30 C31 7.0(2) . . . . ?
N2 C24 C30 C29 -178.22(13) . . . . ?
N2 C24 C25 C26 178.54(14) . . . . ?
N1 C22 C17 C16 6.68(19) . . . . ?
N1 C22 C17 C18 -174.39(12) . . . . ?
N1 C22 C21 C20 176.59(13) . . . . ?
N1 C2 C8 C9 -10.2(2) . . . . ?
N1 C2 C8 C7 176.52(13) . . . . ?
N1 C2 C3 C4 -178.52(14) . . . . ?
C22 N1 C2 C8 -66.61(16) . . . . ?
C22 N1 C2 C3 114.41(15) . . . . ?
C22 C17 C16 C14 131.05(14) . . . . ?
C22 C17 C16 C9 -49.10(18) . . . . ?
C22 C17 C18 C19 -3.3(2) . . . . ?
C22 C21 C20 C19 -1.3(2) . . . . ?
C17 C22 C21 C20 -2.0(2) . . . . ?
C17 C16 C9 C8 2.3(2) . . . . ?
C17 C16 C9 C10 -179.23(12) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C38 C39 C44 N2 -8.1(2) . . . . ?
C38 C39 C44 C43 172.70(14) . . . . ?
C38 C39 C40 C41 -173.45(14) . . . . ?
C38 C31 C30 C24 -46.2(2) . . . . ?
C38 C31 C30 C29 139.14(15) . . . . ?
C38 C31 C32 C33 0.8(2) . . . . ?
C38 C36 C35 C33 -0.2(2) . . . . ?
C39 C38 C31 C30 -2.3(2) . . . . ?
C39 C38 C31 C32 177.88(13) . . . . ?
C39 C38 C36 C35 -178.14(13) . . . . ?
C39 C38 C36 C37 3.4(2) . . . . ?
C39 C44 C43 C42 2.3(2) . . . . ?
C39 C40 C41 C42 -0.7(3) . . . . ?
C14 C16 C9 C8 -177.86(13) . . . . ?
C14 C16 C9 C10 0.6(2) . . . . ?
C16 C17 C18 C19 175.59(13) . . . . ?
C16 C14 C13 C11 -1.4(2) . . . . ?
C16 C9 C8 C2 48.4(2) . . . . ?
C16 C9 C8 C7 -138.44(15) . . . . ?
C16 C9 C10 C11 -1.7(2) . . . . ?
C9 C8 C7 C6 -170.90(14) . . . . ?
C9 C10 C11 C13 1.2(2) . . . . ?
C9 C10 C11 C12 -176.76(15) . . . . ?
C2 N1 C22 C17 70.09(16) . . . . ?
C2 N1 C22 C21 -108.50(14) . . . . ?
C2 C8 C7 C6 2.5(2) . . . . ?
C2 C3 C4 C6 1.6(2) . . . . ?
C2 C3 C4 C5 -177.91(15) . . . . ?
C44 N2 C24 C30 68.57(16) . . . . ?
C44 N2 C24 C25 -111.84(15) . . . . ?
C44 C39 C40 C41 4.6(2) . . . . ?
C44 C43 C42 C41 1.8(2) . . . . ?
C24 N2 C44 C39 -69.01(16) . . . . ?
C24 N2 C44 C43 110.17(15) . . . . ?
C24 C30 C29 C28 -1.1(2) . . . . ?
C24 C25 C26 C28 0.3(2) . . . . ?
C24 C25 C26 C27 -178.91(15) . . . . ?
C31 C38 C39 C44 49.5(2) . . . . ?
C31 C38 C39 C40 -132.57(15) . . . . ?
C31 C38 C36 C35 1.3(2) . . . . ?
C31 C38 C36 C37 -177.23(14) . . . . ?
C31 C30 C29 C28 173.81(14) . . . . ?
C31 C32 C33 C35 0.2(2) . . . . ?
C31 C32 C33 C34 178.14(15) . . . . ?
C8 C9 C10 C11 176.87(13) . . . . ?
C8 C2 C3 C4 2.5(2) . . . . ?
C8 C7 C6 C4 1.7(2) . . . . ?
C30 C24 C25 C26 -1.9(2) . . . . ?
C30 C31 C32 C33 -179.01(14) . . . . ?
C30 C29 C28 C26 -0.5(3) . . . . ?
C10 C9 C8 C2 -130.11(15) . . . . ?
C10 C9 C8 C7 43.0(2) . . . . ?
C10 C11 C13 C14 0.3(2) . . . . ?
C18 C17 C16 C14 -47.85(19) . . . . ?
C18 C17 C16 C9 132.00(14) . . . . ?
C43 C42 C41 C40 -2.6(3) . . . . ?
C3 C2 C8 C9 168.80(13) . . . . ?
C3 C2 C8 C7 -4.5(2) . . . . ?
C3 C4 C6 C7 -3.7(2) . . . . ?
C21 C22 C17 C16 -174.72(12) . . . . ?
C21 C22 C17 C18 4.21(19) . . . . ?
C21 C20 C19 C18 2.2(2) . . . . ?
C25 C24 C30 C31 -172.62(13) . . . . ?
C25 C24 C30 C29 2.2(2) . . . . ?
C25 C26 C28 C29 0.8(2) . . . . ?
C32 C31 C30 C24 133.59(15) . . . . ?
C32 C31 C30 C29 -41.1(2) . . . . ?
C36 C38 C39 C44 -131.13(15) . . . . ?
C36 C38 C39 C40 46.8(2) . . . . ?
C36 C38 C31 C30 178.27(13) . . . . ?
C36 C38 C31 C32 -1.5(2) . . . . ?
C36 C35 C33 C32 -0.5(2) . . . . ?
C36 C35 C33 C34 -178.41(15) . . . . ?
C1 N1 C22 C17 -155.17(12) . . . . ?
C1 N1 C22 C21 26.24(18) . . . . ?
C1 N1 C2 C8 158.91(13) . . . . ?
C1 N1 C2 C3 -20.07(19) . . . . ?
C13 C14 C16 C17 -179.29(13) . . . . ?
C13 C14 C16 C9 0.9(2) . . . . ?
C40 C39 C44 N2 173.88(13) . . . . ?
C40 C39 C44 C43 -5.3(2) . . . . ?
C23 N2 C44 C39 155.52(14) . . . . ?
C23 N2 C44 C43 -25.3(2) . . . . ?
C23 N2 C24 C30 -156.07(14) . . . . ?
C23 N2 C24 C25 23.5(2) . . . . ?
C15 C14 C16 C17 0.1(2) . . . . ?
C15 C14 C16 C9 -179.72(13) . . . . ?
C15 C14 C13 C11 179.16(14) . . . . ?
C37 C36 C35 C33 178.34(15) . . . . ?
C12 C11 C13 C14 178.32(14) . . . . ?
C27 C26 C28 C29 -179.92(16) . . . . ?
C5 C4 C6 C7 175.82(16) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.500 0.000 0.500 204.0 49.9 '1 C4H8O2'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
