# Supplementary Information (SI) for Chemical Communications.
# 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_Prek_dcm_cyclohex
_database_code_depnum_ccdc_archive 'CCDC 2311971'
loop_
_audit_author_name
_audit_author_address
'Anna Pietrzak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2023-12-04 deposited with the CCDC.	2024-11-25 downloaded from the CCDC.
;
_audit_creation_date             2023-12-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C35 H21 N3 O'
_chemical_formula_sum            'C35 H21 N3 O'
_chemical_formula_weight         499.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   15.5452(2)
_cell_length_b                   4.78961(6)
_cell_length_c                   32.4950(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.4880(13)
_cell_angle_gamma                90
_cell_volume                     2352.70(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18941
_cell_measurement_temperature    100.02(12)
_cell_measurement_theta_max      78.4800
_cell_measurement_theta_min      2.9260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            28677
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.816
_diffrn_reflns_theta_min         2.797
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4426
_reflns_number_total             4812
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.00030(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/3 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4812
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.040
_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)+(0.0405P)²+0.9174P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0852
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C15(H15), C18(H18), C19(H19), C22(H22), C23(H23), C26(H26), C27(H27), C30(H30),
  C31(H31), C32(H32), C33(H33), C34(H34), C35(H35)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_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 0.75123(5) 0.64417(16) 0.41222(2) 0.02315(17) Uani 1 1 d . . . . .
N1 N 0.73990(6) -0.03700(19) 0.51704(3) 0.02049(19) Uani 1 1 d . . . . .
C1 C 0.87459(7) -0.2944(2) 0.54534(3) 0.0192(2) Uani 1 1 d . . . . .
N2 N 0.82932(6) 0.24231(19) 0.46451(3) 0.02100(19) Uani 1 1 d . . . . .
C2 C 0.96379(7) -0.3433(2) 0.54669(3) 0.0222(2) Uani 1 1 d . . . . .
H2 H 0.992859 -0.237601 0.529222 0.027 Uiso 1 1 calc R U . . .
N3 N 0.86942(6) 0.05203(19) 0.49077(3) 0.02099(19) Uani 1 1 d . . . . .
C3 C 1.01016(7) -0.5466(2) 0.57355(3) 0.0241(2) Uani 1 1 d . . . . .
H3 H 1.070779 -0.579523 0.574314 0.029 Uiso 1 1 calc R U . . .
C4 C 0.96820(7) -0.7013(2) 0.59921(3) 0.0236(2) Uani 1 1 d . . . . .
H4 H 0.999958 -0.839942 0.617536 0.028 Uiso 1 1 calc R U . . .
C5 C 0.87931(7) -0.6525(2) 0.59801(3) 0.0248(2) Uani 1 1 d . . . . .
H5 H 0.850368 -0.758613 0.615484 0.030 Uiso 1 1 calc R U . . .
C6 C 0.83299(7) -0.4496(2) 0.57140(3) 0.0224(2) Uani 1 1 d . . . . .
H6 H 0.772529 -0.416116 0.570912 0.027 Uiso 1 1 calc R U . . .
C7 C 0.82360(7) -0.0824(2) 0.51656(3) 0.0190(2) Uani 1 1 d . . . . .
C8 C 0.69726(6) 0.1601(2) 0.48973(3) 0.0195(2) Uani 1 1 d . . . . .
C9 C 0.74287(6) 0.3011(2) 0.46303(3) 0.0185(2) Uani 1 1 d . . . . .
C10 C 0.60763(7) 0.2262(2) 0.48788(3) 0.0229(2) Uani 1 1 d . . . . .
H10 H 0.575945 0.131546 0.505393 0.027 Uiso 1 1 calc R U . . .
C11 C 0.56760(7) 0.4292(2) 0.46037(3) 0.0236(2) Uani 1 1 d . . . . .
H11 H 0.507581 0.474657 0.459185 0.028 Uiso 1 1 calc R U . . .
C12 C 0.61233(7) 0.5738(2) 0.43363(3) 0.0221(2) Uani 1 1 d . . . . .
H12 H 0.582468 0.714517 0.415078 0.027 Uiso 1 1 calc R U . . .
C13 C 0.69881(7) 0.5111(2) 0.43447(3) 0.0197(2) Uani 1 1 d . . . . .
C14 C 0.71837(7) 0.7987(2) 0.37556(3) 0.0198(2) Uani 1 1 d . . . . .
C15 C 0.64150(7) 0.7395(2) 0.34628(3) 0.0190(2) Uani 1 1 d . . . . .
H15 H 0.603554 0.595633 0.351709 0.023 Uiso 1 1 calc R U . . .
C16 C 0.61858(7) 0.8928(2) 0.30789(3) 0.0188(2) Uani 1 1 d . . . . .
C17 C 0.67961(7) 1.0935(2) 0.29952(3) 0.0213(2) Uani 1 1 d . . . . .
C18 C 0.75699(7) 1.1516(2) 0.33102(4) 0.0233(2) Uani 1 1 d . . . . .
H18 H 0.796301 1.292604 0.326027 0.028 Uiso 1 1 calc R U . . .
C19 C 0.77655(7) 1.0092(2) 0.36853(3) 0.0225(2) Uani 1 1 d . . . . .
H19 H 0.828547 1.051676 0.389509 0.027 Uiso 1 1 calc R U . . .
C20 C 0.54026(7) 0.8282(2) 0.27506(3) 0.0195(2) Uani 1 1 d . . . . .
C21 C 0.54077(7) 0.9076(2) 0.23314(3) 0.0226(2) Uani 1 1 d . . . . .
C22 C 0.60227(7) 1.1139(2) 0.22606(3) 0.0255(2) Uani 1 1 d . . . . .
H22 H 0.598457 1.180476 0.198159 0.031 Uiso 1 1 calc R U . . .
C23 C 0.66576(7) 1.2159(2) 0.25833(4) 0.0252(2) Uani 1 1 d . . . . .
H23 H 0.701184 1.368896 0.253643 0.030 Uiso 1 1 calc R U . . .
C24 C 0.46482(7) 0.6745(2) 0.28168(3) 0.0191(2) Uani 1 1 d . . . . .
C25 C 0.41358(7) 0.5249(2) 0.24710(3) 0.0223(2) Uani 1 1 d . . . . .
C26 C 0.42494(7) 0.5765(3) 0.20553(3) 0.0269(2) Uani 1 1 d . . . . .
H26 H 0.392815 0.468723 0.182472 0.032 Uiso 1 1 calc R U . . .
C27 C 0.48118(8) 0.7779(3) 0.19855(3) 0.0268(2) Uani 1 1 d . . . . .
H27 H 0.480753 0.832693 0.170403 0.032 Uiso 1 1 calc R U . . .
C28 C 0.43102(6) 0.6920(2) 0.31985(3) 0.0187(2) Uani 1 1 d . . . . .
C29 C 0.35937(7) 0.5177(2) 0.32375(3) 0.0212(2) Uani 1 1 d . . . . .
C30 C 0.32231(7) 0.3256(2) 0.29070(4) 0.0242(2) Uani 1 1 d . . . . .
H30 H 0.280594 0.190194 0.294957 0.029 Uiso 1 1 calc R U . . .
C31 C 0.34657(7) 0.3364(2) 0.25333(4) 0.0249(2) Uani 1 1 d . . . . .
H31 H 0.318554 0.216688 0.230884 0.030 Uiso 1 1 calc R U . . .
C32 C 0.45722(6) 0.9037(2) 0.35070(3) 0.0197(2) Uani 1 1 d . . . . .
H32 H 0.502848 1.029655 0.348090 0.024 Uiso 1 1 calc R U . . .
C33 C 0.41799(7) 0.9309(2) 0.38441(3) 0.0218(2) Uani 1 1 d . . . . .
H33 H 0.437123 1.074166 0.404711 0.026 Uiso 1 1 calc R U . . .
C34 C 0.35015(7) 0.7494(2) 0.38903(3) 0.0245(2) Uani 1 1 d . . . . .
H34 H 0.324371 0.765923 0.412706 0.029 Uiso 1 1 calc R U . . .
C35 C 0.32133(7) 0.5476(2) 0.35902(4) 0.0246(2) Uani 1 1 d . . . . .
H35 H 0.274969 0.425609 0.361985 0.029 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 C13 1.3667(12) . ?
O1 C14 1.3944(12) . ?
N1 C7 1.3230(13) . ?
N1 C8 1.3577(14) . ?
C1 C2 1.3969(14) . ?
C1 C6 1.3941(15) . ?
C1 C7 1.4793(14) . ?
N2 N3 1.3036(12) . ?
N2 C9 1.3629(13) . ?
C2 H2 0.9500 . ?
C2 C3 1.3912(15) . ?
N3 C7 1.3791(13) . ?
C3 H3 0.9500 . ?
C3 C4 1.3869(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3929(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3855(15) . ?
C6 H6 0.9500 . ?
C8 C9 1.4139(14) . ?
C8 C10 1.4165(14) . ?
C9 C13 1.4301(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3684(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.4143(15) . ?
C12 H12 0.9500 . ?
C12 C13 1.3715(14) . ?
C14 C15 1.3722(14) . ?
C14 C19 1.4084(15) . ?
C15 H15 0.9500 . ?
C15 C16 1.4194(14) . ?
C16 C17 1.4208(15) . ?
C16 C20 1.4526(14) . ?
C17 C18 1.4134(15) . ?
C17 C23 1.4307(15) . ?
C18 H18 0.9500 . ?
C18 C19 1.3673(16) . ?
C19 H19 0.9500 . ?
C20 C21 1.4162(14) . ?
C20 C24 1.4426(14) . ?
C21 C22 1.4300(16) . ?
C21 C27 1.4219(16) . ?
C22 H22 0.9500 . ?
C22 C23 1.3527(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.4119(15) . ?
C24 C28 1.4579(14) . ?
C25 C26 1.4241(16) . ?
C25 C31 1.4278(16) . ?
C26 H26 0.9500 . ?
C26 C27 1.3564(17) . ?
C27 H27 0.9500 . ?
C28 C29 1.4211(14) . ?
C28 C32 1.4170(14) . ?
C29 C30 1.4295(15) . ?
C29 C35 1.4139(15) . ?
C30 H30 0.9500 . ?
C30 C31 1.3539(16) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C32 C33 1.3787(14) . ?
C33 H33 0.9500 . ?
C33 C34 1.4017(15) . ?
C34 H34 0.9500 . ?
C34 C35 1.3720(16) . ?
C35 H35 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
C13 O1 C14 123.69(8) . . ?
C7 N1 C8 115.97(9) . . ?
C2 C1 C7 121.11(9) . . ?
C6 C1 C2 119.28(10) . . ?
C6 C1 C7 119.61(9) . . ?
N3 N2 C9 118.98(9) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.16(10) . . ?
C3 C2 H2 119.9 . . ?
N2 N3 C7 119.22(8) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.22(10) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.75(10) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.19(10) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.39(10) . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C1 119.25(9) . . ?
N1 C7 N3 125.41(10) . . ?
N3 C7 C1 115.34(9) . . ?
N1 C8 C9 119.68(9) . . ?
N1 C8 C10 120.57(9) . . ?
C9 C8 C10 119.75(10) . . ?
N2 C9 C8 120.74(9) . . ?
N2 C9 C13 119.16(9) . . ?
C8 C9 C13 120.09(9) . . ?
C8 C10 H10 120.7 . . ?
C11 C10 C8 118.65(10) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 118.8 . . ?
C10 C11 C12 122.38(10) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.04(10) . . ?
C13 C12 H12 120.0 . . ?
O1 C13 C9 114.63(8) . . ?
O1 C13 C12 126.15(10) . . ?
C12 C13 C9 119.07(9) . . ?
O1 C14 C19 113.42(9) . . ?
C15 C14 O1 124.69(9) . . ?
C15 C14 C19 121.58(10) . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.13(9) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 118.44(9) . . ?
C15 C16 C20 122.06(9) . . ?
C17 C16 C20 119.09(9) . . ?
C16 C17 C23 119.66(10) . . ?
C18 C17 C16 119.20(10) . . ?
C18 C17 C23 120.92(10) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.48(10) . . ?
C19 C18 H18 119.3 . . ?
C14 C19 H19 120.5 . . ?
C18 C19 C14 118.94(10) . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C16 117.23(9) . . ?
C21 C20 C24 117.87(9) . . ?
C24 C20 C16 124.78(9) . . ?
C20 C21 C22 119.61(10) . . ?
C20 C21 C27 119.63(10) . . ?
C27 C21 C22 120.75(10) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.28(10) . . ?
C23 C22 H22 119.4 . . ?
C17 C23 H23 120.0 . . ?
C22 C23 C17 120.03(10) . . ?
C22 C23 H23 120.0 . . ?
C20 C24 C28 124.35(9) . . ?
C25 C24 C20 117.89(9) . . ?
C25 C24 C28 117.25(9) . . ?
C24 C25 C26 119.67(10) . . ?
C24 C25 C31 120.19(10) . . ?
C26 C25 C31 120.00(10) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.63(10) . . ?
C27 C26 H26 119.7 . . ?
C21 C27 H27 119.8 . . ?
C26 C27 C21 120.34(10) . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C24 119.19(9) . . ?
C32 C28 C24 122.81(9) . . ?
C32 C28 C29 117.32(9) . . ?
C28 C29 C30 119.86(10) . . ?
C35 C29 C28 119.84(10) . . ?
C35 C29 C30 120.18(10) . . ?
C29 C30 H30 119.9 . . ?
C31 C30 C29 120.11(10) . . ?
C31 C30 H30 119.9 . . ?
C25 C31 H31 119.5 . . ?
C30 C31 C25 121.09(10) . . ?
C30 C31 H31 119.5 . . ?
C28 C32 H32 119.2 . . ?
C33 C32 C28 121.50(10) . . ?
C33 C32 H32 119.2 . . ?
C32 C33 H33 119.7 . . ?
C32 C33 C34 120.63(10) . . ?
C34 C33 H33 119.7 . . ?
C33 C34 H34 120.3 . . ?
C35 C34 C33 119.34(10) . . ?
C35 C34 H34 120.3 . . ?
C29 C35 H35 119.4 . . ?
C34 C35 C29 121.23(10) . . ?
C34 C35 H35 119.4 . . ?

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 C14 C15 C16 -173.53(9) . . . . ?
O1 C14 C19 C18 171.82(9) . . . . ?
N1 C8 C9 N2 -0.26(15) . . . . ?
N1 C8 C9 C13 -179.35(9) . . . . ?
N1 C8 C10 C11 178.99(10) . . . . ?
C1 C2 C3 C4 -0.16(17) . . . . ?
N2 N3 C7 N1 0.55(16) . . . . ?
N2 N3 C7 C1 -179.87(9) . . . . ?
N2 C9 C13 O1 -2.91(14) . . . . ?
N2 C9 C13 C12 -178.72(10) . . . . ?
C2 C1 C6 C5 -0.72(16) . . . . ?
C2 C1 C7 N1 -178.20(10) . . . . ?
C2 C1 C7 N3 2.19(15) . . . . ?
C2 C3 C4 C5 0.01(17) . . . . ?
N3 N2 C9 C8 0.48(15) . . . . ?
N3 N2 C9 C13 179.58(9) . . . . ?
C3 C4 C5 C6 -0.22(17) . . . . ?
C4 C5 C6 C1 0.58(17) . . . . ?
C6 C1 C2 C3 0.51(16) . . . . ?
C6 C1 C7 N1 2.24(15) . . . . ?
C6 C1 C7 N3 -177.37(10) . . . . ?
C7 N1 C8 C9 0.17(14) . . . . ?
C7 N1 C8 C10 -179.59(10) . . . . ?
C7 C1 C2 C3 -179.06(10) . . . . ?
C7 C1 C6 C5 178.85(10) . . . . ?
C8 N1 C7 C1 -179.88(9) . . . . ?
C8 N1 C7 N3 -0.31(15) . . . . ?
C8 C9 C13 O1 176.20(9) . . . . ?
C8 C9 C13 C12 0.38(15) . . . . ?
C8 C10 C11 C12 0.34(17) . . . . ?
C9 N2 N3 C7 -0.60(14) . . . . ?
C9 C8 C10 C11 -0.76(16) . . . . ?
C10 C8 C9 N2 179.50(10) . . . . ?
C10 C8 C9 C13 0.41(15) . . . . ?
C10 C11 C12 C13 0.46(17) . . . . ?
C11 C12 C13 O1 -176.10(10) . . . . ?
C11 C12 C13 C9 -0.81(16) . . . . ?
C13 O1 C14 C15 -32.74(15) . . . . ?
C13 O1 C14 C19 153.62(9) . . . . ?
C14 O1 C13 C9 162.43(9) . . . . ?
C14 O1 C13 C12 -22.10(16) . . . . ?
C14 C15 C16 C17 4.17(14) . . . . ?
C14 C15 C16 C20 176.80(9) . . . . ?
C15 C14 C19 C18 -2.04(16) . . . . ?
C15 C16 C17 C18 -5.54(14) . . . . ?
C15 C16 C17 C23 169.18(9) . . . . ?
C15 C16 C20 C21 -155.34(10) . . . . ?
C15 C16 C20 C24 20.61(15) . . . . ?
C16 C17 C18 C19 3.25(16) . . . . ?
C16 C17 C23 C22 -9.10(16) . . . . ?
C16 C20 C21 C22 -18.69(14) . . . . ?
C16 C20 C21 C27 160.22(9) . . . . ?
C16 C20 C24 C25 -152.93(10) . . . . ?
C16 C20 C24 C28 35.45(15) . . . . ?
C17 C16 C20 C21 17.24(14) . . . . ?
C17 C16 C20 C24 -166.81(9) . . . . ?
C17 C18 C19 C14 0.57(16) . . . . ?
C18 C17 C23 C22 165.53(10) . . . . ?
C19 C14 C15 C16 -0.39(15) . . . . ?
C20 C16 C17 C18 -178.39(9) . . . . ?
C20 C16 C17 C23 -3.67(14) . . . . ?
C20 C21 C22 C23 6.38(16) . . . . ?
C20 C21 C27 C26 -0.92(16) . . . . ?
C20 C24 C25 C26 -13.60(14) . . . . ?
C20 C24 C25 C31 170.60(9) . . . . ?
C20 C24 C28 C29 -176.26(9) . . . . ?
C20 C24 C28 C32 13.46(15) . . . . ?
C21 C20 C24 C25 23.00(14) . . . . ?
C21 C20 C24 C28 -148.62(10) . . . . ?
C21 C22 C23 C17 7.86(16) . . . . ?
C22 C21 C27 C26 177.98(10) . . . . ?
C23 C17 C18 C19 -171.41(10) . . . . ?
C24 C20 C21 C22 165.08(9) . . . . ?
C24 C20 C21 C27 -16.02(14) . . . . ?
C24 C25 C26 C27 -3.40(16) . . . . ?
C24 C25 C31 C30 9.26(15) . . . . ?
C24 C28 C29 C30 0.89(14) . . . . ?
C24 C28 C29 C35 -175.05(9) . . . . ?
C24 C28 C32 C33 173.73(9) . . . . ?
C25 C24 C28 C29 12.07(14) . . . . ?
C25 C24 C28 C32 -158.22(10) . . . . ?
C25 C26 C27 C21 10.87(16) . . . . ?
C26 C25 C31 C30 -166.53(10) . . . . ?
C27 C21 C22 C23 -172.51(10) . . . . ?
C28 C24 C25 C26 158.63(10) . . . . ?
C28 C24 C25 C31 -17.18(14) . . . . ?
C28 C29 C30 C31 -9.33(15) . . . . ?
C28 C29 C35 C34 2.41(16) . . . . ?
C28 C32 C33 C34 -0.36(16) . . . . ?
C29 C28 C32 C33 3.27(14) . . . . ?
C29 C30 C31 C25 4.37(16) . . . . ?
C30 C29 C35 C34 -173.53(10) . . . . ?
C31 C25 C26 C27 172.41(10) . . . . ?
C32 C28 C29 C30 171.71(9) . . . . ?
C32 C28 C29 C35 -4.24(14) . . . . ?
C32 C33 C34 C35 -1.64(16) . . . . ?
C33 C34 C35 C29 0.60(16) . . . . ?
C35 C29 C30 C31 166.60(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.304
_oxdiff_exptl_absorpt_empirical_full_min 0.555
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dicloromethane and cyclohexane mixture'
####################################################################### 
# 
# 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_5hel_DCM_MeCN
_database_code_depnum_ccdc_archive 'CCDC 2339405'
loop_
_audit_author_name
_audit_author_address
'Anna Pietrzak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2024-03-11 deposited with the CCDC.	2024-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H16 N3 O'
_chemical_formula_sum            'C27 H16 N3 O'
_chemical_formula_weight         398.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   43.1890(5)
_cell_length_b                   43.1890(5)
_cell_length_c                   5.1711(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8353.3(5)
_cell_formula_units_Z            18
_cell_measurement_temperature    100.01(11)
_cell_measurement_reflns_used    12698
_cell_measurement_theta_min      3.5250
_cell_measurement_theta_max      77.9290

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             3726
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.028
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.703
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_T_min  0.498
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.641
_oxdiff_exptl_absorpt_empirical_full_max 2.344
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100.01(11)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28218
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_k_max       53
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.545
_diffrn_reflns_theta_max         78.750
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3920
_reflns_number_gt                3106
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 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.
;

_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2019/3 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          SQUEEZE
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+7.3502P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3920
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1022
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.62589(2) 0.54639(2) 1.19169(17) 0.0300(2) Uani 1 1 d . . . . .
N1 N 0.64052(3) 0.48330(3) 0.6575(2) 0.0288(3) Uani 1 1 d . . . . .
C1 C 0.62063(4) 0.44257(3) 0.3058(2) 0.0294(3) Uani 1 1 d . . . . .
N2 N 0.63525(3) 0.50418(3) 0.8272(2) 0.0274(2) Uani 1 1 d . . . . .
C2 C 0.59630(4) 0.42359(4) 0.1089(3) 0.0324(3) Uani 1 1 d . . . . .
H2 H 0.575541 0.425610 0.087268 0.039 Uiso 1 1 calc R U . . .
N3 N 0.58442(3) 0.46770(3) 0.4521(2) 0.0312(3) Uani 1 1 d . . . . .
C3 C 0.60240(4) 0.40179(4) -0.0551(3) 0.0351(3) Uani 1 1 d . . . . .
H3 H 0.585885 0.389137 -0.189754 0.042 Uiso 1 1 calc R U . . .
C5 C 0.65654(4) 0.41699(4) 0.1724(3) 0.0392(3) Uani 1 1 d . . . . .
H5 H 0.677093 0.414612 0.194658 0.047 Uiso 1 1 calc R U . . .
C6 C 0.65082(4) 0.43892(4) 0.3350(3) 0.0351(3) Uani 1 1 d . . . . .
H6 H 0.667553 0.451677 0.468288 0.042 Uiso 1 1 calc R U . . .
C7 C 0.61447(4) 0.46616(3) 0.4832(2) 0.0287(3) Uani 1 1 d . . . . .
C8 C 0.60478(3) 0.50705(3) 0.8230(2) 0.0275(3) Uani 1 1 d . . . . .
C9 C 0.57931(4) 0.48860(3) 0.6296(2) 0.0299(3) Uani 1 1 d . . . . .
C10 C 0.66216(3) 0.52388(3) 1.0087(2) 0.0268(3) Uani 1 1 d . . . . .
C11 C 0.65734(3) 0.54522(3) 1.1877(2) 0.0264(3) Uani 1 1 d . . . . .
C12 C 0.60046(3) 0.52831(4) 1.0042(2) 0.0289(3) Uani 1 1 d . . . . .
C13 C 0.69356(4) 0.52198(4) 1.0054(3) 0.0300(3) Uani 1 1 d . . . . .
H13 H 0.696477 0.507101 0.884210 0.036 Uiso 1 1 calc R U . . .
C14 C 0.71991(4) 0.54184(4) 1.1789(3) 0.0318(3) Uani 1 1 d . . . . .
H14 H 0.741279 0.540639 1.177509 0.038 Uiso 1 1 calc R U . . .
C15 C 0.71615(4) 0.56409(3) 1.3601(2) 0.0287(3) Uani 1 1 d . . . . .
C16 C 0.68418(3) 0.56624(3) 1.3708(2) 0.0269(3) Uani 1 1 d . . . . .
C17 C 0.54883(4) 0.49244(4) 0.6240(3) 0.0346(3) Uani 1 1 d . . . . .
H17 H 0.530953 0.480337 0.496220 0.042 Uiso 1 1 calc R U . . .
C18 C 0.57053(4) 0.53184(4) 0.9966(3) 0.0336(3) Uani 1 1 d . . . . .
H18 H 0.567310 0.546306 1.119884 0.040 Uiso 1 1 calc R U . . .
C19 C 0.54492(4) 0.51380(4) 0.8045(3) 0.0363(3) Uani 1 1 d . . . . .
H19 H 0.524299 0.516315 0.797930 0.044 Uiso 1 1 calc R U . . .
C20 C 0.74515(4) 0.58473(4) 1.5328(3) 0.0316(3) Uani 1 1 d . . . . .
H20 H 0.766337 0.583285 1.520824 0.038 Uiso 1 1 calc R U . . .
C21 C 0.74298(4) 0.60618(4) 1.7119(3) 0.0320(3) Uani 1 1 d . . . . .
H21 H 0.762664 0.619642 1.824039 0.038 Uiso 1 1 calc R U . . .
C22 C 0.71151(4) 0.60902(4) 1.7362(2) 0.0293(3) Uani 1 1 d . . . . .
C23 C 0.68175(4) 0.58957(3) 1.5667(2) 0.0275(3) Uani 1 1 d . . . . .
C24 C 0.70957(4) 0.63050(4) 1.9338(2) 0.0313(3) Uani 1 1 d . . . . .
H24 H 0.729446 0.643268 2.045749 0.038 Uiso 1 1 calc R U . . .
C25 C 0.65155(4) 0.59372(4) 1.6060(2) 0.0299(3) Uani 1 1 d . . . . .
H25 H 0.631474 0.581645 1.494715 0.036 Uiso 1 1 calc R U . . .
C26 C 0.65063(4) 0.61486(4) 1.8017(2) 0.0315(3) Uani 1 1 d . . . . .
H26 H 0.629897 0.616911 1.824092 0.038 Uiso 1 1 calc R U . . .
C27 C 0.67970(4) 0.63331(4) 1.9676(2) 0.0321(3) Uani 1 1 d . . . . .
H27 H 0.678723 0.647687 2.102862 0.039 Uiso 1 1 calc R U . . .
C29 C 0.63233(4) 0.39833(4) -0.0243(3) 0.0371(3) Uani 1 1 d . . . . .
H29 H 0.636326 0.383289 -0.136788 0.045 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 C12 1.3778(15) . ?
O1 C11 1.3849(15) . ?
N1 C7 1.3391(17) . ?
N1 N2 1.3570(15) . ?
C1 C2 1.3971(19) . ?
C1 C6 1.398(2) . ?
C1 C7 1.4903(18) . ?
N2 C8 1.3822(16) . ?
N2 C10 1.4023(16) . ?
C2 C3 1.386(2) . ?
C2 H2 0.9500 . ?
N3 C7 1.3421(17) . ?
N3 C9 1.3800(17) . ?
C3 C29 1.383(2) . ?
C3 H3 0.9500 . ?
C5 C6 1.378(2) . ?
C5 C29 1.391(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C12 1.3884(18) . ?
C8 C9 1.4033(18) . ?
C9 C17 1.4068(19) . ?
C10 C11 1.3931(18) . ?
C10 C13 1.3989(18) . ?
C11 C16 1.4183(18) . ?
C12 C18 1.3759(19) . ?
C13 C14 1.3637(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.4085(18) . ?
C14 H14 0.9500 . ?
C15 C20 1.4297(19) . ?
C15 C16 1.4304(18) . ?
C16 C23 1.4695(18) . ?
C17 C19 1.381(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3985(19) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.3461(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.4299(19) . ?
C21 H21 0.9500 . ?
C22 C24 1.4107(19) . ?
C22 C23 1.4303(18) . ?
C23 C25 1.4173(19) . ?
C24 C27 1.366(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.3765(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.395(2) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C29 H29 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
C12 O1 C11 119.15(10) . . ?
C7 N1 N2 115.40(11) . . ?
C2 C1 C6 118.87(13) . . ?
C2 C1 C7 120.73(12) . . ?
C6 C1 C7 120.39(12) . . ?
N1 N2 C8 122.20(11) . . ?
N1 N2 C10 118.21(11) . . ?
C8 N2 C10 119.58(11) . . ?
C3 C2 C1 120.12(13) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C7 N3 C9 115.33(11) . . ?
C29 C3 C2 120.54(13) . . ?
C29 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C6 C5 C29 120.19(14) . . ?
C6 C5 H5 119.9 . . ?
C29 C5 H5 119.9 . . ?
C5 C6 C1 120.63(13) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N1 C7 N3 128.27(12) . . ?
N1 C7 C1 113.84(12) . . ?
N3 C7 C1 117.89(12) . . ?
N2 C8 C12 119.83(12) . . ?
N2 C8 C9 118.15(12) . . ?
C12 C8 C9 122.01(12) . . ?
N3 C9 C8 120.59(12) . . ?
N3 C9 C17 121.91(12) . . ?
C8 C9 C17 117.50(12) . . ?
C11 C10 C13 121.11(12) . . ?
C11 C10 N2 119.56(12) . . ?
C13 C10 N2 119.33(12) . . ?
O1 C11 C10 120.53(11) . . ?
O1 C11 C16 117.98(11) . . ?
C10 C11 C16 121.49(12) . . ?
C18 C12 O1 118.94(12) . . ?
C18 C12 C8 119.91(12) . . ?
O1 C12 C8 121.14(12) . . ?
C14 C13 C10 118.92(12) . . ?
C14 C13 H13 120.5 . . ?
C10 C13 H13 120.5 . . ?
C13 C14 C15 121.48(13) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C20 118.49(12) . . ?
C14 C15 C16 120.94(12) . . ?
C20 C15 C16 120.56(12) . . ?
C11 C16 C15 116.05(12) . . ?
C11 C16 C23 125.70(12) . . ?
C15 C16 C23 118.26(12) . . ?
C19 C17 C9 119.95(13) . . ?
C19 C17 H17 120.0 . . ?
C9 C17 H17 120.0 . . ?
C12 C18 C19 118.92(13) . . ?
C12 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C17 C19 C18 121.70(13) . . ?
C17 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C21 C20 C15 121.22(13) . . ?
C21 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
C20 C21 C22 121.02(13) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C24 C22 C21 119.43(13) . . ?
C24 C22 C23 119.90(12) . . ?
C21 C22 C23 120.65(12) . . ?
C25 C23 C22 116.86(12) . . ?
C25 C23 C16 124.85(12) . . ?
C22 C23 C16 118.27(12) . . ?
C27 C24 C22 121.36(13) . . ?
C27 C24 H24 119.3 . . ?
C22 C24 H24 119.3 . . ?
C26 C25 C23 121.51(13) . . ?
C26 C25 H25 119.2 . . ?
C23 C25 H25 119.2 . . ?
C25 C26 C27 120.99(13) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C24 C27 C26 119.37(12) . . ?
C24 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
C3 C29 C5 119.63(14) . . ?
C3 C29 H29 120.2 . . ?
C5 C29 H29 120.2 . . ?

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
C7 N1 N2 C8 1.04(17) . . . . ?
C7 N1 N2 C10 -177.69(11) . . . . ?
C6 C1 C2 C3 -0.5(2) . . . . ?
C7 C1 C2 C3 179.87(12) . . . . ?
C1 C2 C3 C29 0.6(2) . . . . ?
C29 C5 C6 C1 0.3(2) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C7 C1 C6 C5 179.65(13) . . . . ?
N2 N1 C7 N3 1.66(19) . . . . ?
N2 N1 C7 C1 -178.07(10) . . . . ?
C9 N3 C7 N1 -2.7(2) . . . . ?
C9 N3 C7 C1 177.00(11) . . . . ?
C2 C1 C7 N1 -178.34(12) . . . . ?
C6 C1 C7 N1 2.07(18) . . . . ?
C2 C1 C7 N3 1.91(18) . . . . ?
C6 C1 C7 N3 -177.69(12) . . . . ?
N1 N2 C8 C12 178.84(11) . . . . ?
C10 N2 C8 C12 -2.45(18) . . . . ?
N1 N2 C8 C9 -2.33(18) . . . . ?
C10 N2 C8 C9 176.38(11) . . . . ?
C7 N3 C9 C8 1.14(18) . . . . ?
C7 N3 C9 C17 -179.14(12) . . . . ?
N2 C8 C9 N3 1.16(18) . . . . ?
C12 C8 C9 N3 179.96(12) . . . . ?
N2 C8 C9 C17 -178.57(12) . . . . ?
C12 C8 C9 C17 0.23(19) . . . . ?
N1 N2 C10 C11 -179.19(11) . . . . ?
C8 N2 C10 C11 2.05(17) . . . . ?
N1 N2 C10 C13 1.32(17) . . . . ?
C8 N2 C10 C13 -177.44(12) . . . . ?
C12 O1 C11 C10 -4.81(17) . . . . ?
C12 O1 C11 C16 175.30(11) . . . . ?
C13 C10 C11 O1 -178.91(11) . . . . ?
N2 C10 C11 O1 1.60(18) . . . . ?
C13 C10 C11 C16 0.97(19) . . . . ?
N2 C10 C11 C16 -178.51(11) . . . . ?
C11 O1 C12 C18 -174.90(12) . . . . ?
C11 O1 C12 C8 4.43(18) . . . . ?
N2 C8 C12 C18 178.52(12) . . . . ?
C9 C8 C12 C18 -0.3(2) . . . . ?
N2 C8 C12 O1 -0.80(19) . . . . ?
C9 C8 C12 O1 -179.59(12) . . . . ?
C11 C10 C13 C14 -0.9(2) . . . . ?
N2 C10 C13 C14 178.58(11) . . . . ?
C10 C13 C14 C15 0.0(2) . . . . ?
C13 C14 C15 C20 -178.72(12) . . . . ?
C13 C14 C15 C16 0.9(2) . . . . ?
O1 C11 C16 C15 179.79(11) . . . . ?
C10 C11 C16 C15 -0.10(18) . . . . ?
O1 C11 C16 C23 -0.17(19) . . . . ?
C10 C11 C16 C23 179.94(12) . . . . ?
C14 C15 C16 C11 -0.81(18) . . . . ?
C20 C15 C16 C11 178.80(11) . . . . ?
C14 C15 C16 C23 179.15(11) . . . . ?
C20 C15 C16 C23 -1.23(18) . . . . ?
N3 C9 C17 C19 -179.61(13) . . . . ?
C8 C9 C17 C19 0.1(2) . . . . ?
O1 C12 C18 C19 179.28(12) . . . . ?
C8 C12 C18 C19 -0.1(2) . . . . ?
C9 C17 C19 C18 -0.4(2) . . . . ?
C12 C18 C19 C17 0.4(2) . . . . ?
C14 C15 C20 C21 -179.27(13) . . . . ?
C16 C15 C20 C21 1.1(2) . . . . ?
C15 C20 C21 C22 0.1(2) . . . . ?
C20 C21 C22 C24 177.11(12) . . . . ?
C20 C21 C22 C23 -1.2(2) . . . . ?
C24 C22 C23 C25 1.18(18) . . . . ?
C21 C22 C23 C25 179.46(12) . . . . ?
C24 C22 C23 C16 -177.30(11) . . . . ?
C21 C22 C23 C16 0.98(18) . . . . ?
C11 C16 C23 C25 1.8(2) . . . . ?
C15 C16 C23 C25 -178.14(12) . . . . ?
C11 C16 C23 C22 -179.84(12) . . . . ?
C15 C16 C23 C22 0.20(17) . . . . ?
C21 C22 C24 C27 -178.47(12) . . . . ?
C23 C22 C24 C27 -0.17(19) . . . . ?
C22 C23 C25 C26 -1.41(19) . . . . ?
C16 C23 C25 C26 176.95(12) . . . . ?
C23 C25 C26 C27 0.6(2) . . . . ?
C22 C24 C27 C26 -0.7(2) . . . . ?
C25 C26 C27 C24 0.4(2) . . . . ?
C2 C3 C29 C5 -0.2(2) . . . . ?
C6 C5 C29 C3 -0.2(2) . . . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.035




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: mixture of  dichloromethane and acetinitrile'
####################################################################### 
# 
# 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_Helicen
_database_code_depnum_ccdc_archive 'CCDC 2312391'
loop_
_audit_author_name
_audit_author_address
'Anna Pietrzak'
;Lodz University of Technology
Poland
;
_audit_update_record             
;
2023-12-06 deposited with the CCDC.	2024-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H20 N3 O'
_chemical_formula_sum            'C35 H20 N3 O'
_chemical_formula_weight         498.54

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   21.3059(3)
_cell_length_b                   11.4684(2)
_cell_length_c                   9.68440(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.6850(10)
_cell_angle_gamma                90
_cell_volume                     2358.42(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    29555
_cell_measurement_theta_min      3.8830
_cell_measurement_theta_max      79.2120

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             1036
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.675
_shelx_estimated_absorpt_T_min   0.729
_shelx_estimated_absorpt_T_max   0.929
_exptl_absorpt_correction_T_min  0.59939
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.497
_oxdiff_exptl_absorpt_empirical_full_max 1.947
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44352
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.164
_diffrn_reflns_theta_max         79.685
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4960
_reflns_number_gt                4557
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+0.8723P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4960
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1013
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.76984(3) 0.44415(7) 0.78923(7) 0.02044(17) Uani 1 1 d . . . . .
N1 N 0.60656(4) 0.57065(8) 0.57640(9) 0.0203(2) Uani 1 1 d . . . . .
C1 C 0.53816(5) 0.58198(9) 0.36860(11) 0.0210(2) Uani 1 1 d . . . . .
N2 N 0.65898(4) 0.52525(8) 0.64638(9) 0.01893(19) Uani 1 1 d . . . . .
C2 C 0.52292(5) 0.54741(11) 0.23199(12) 0.0263(2) Uani 1 1 d . . . . .
H2 H 0.548419 0.491544 0.190538 0.032 Uiso 1 1 calc R U . . .
N3 N 0.62673(4) 0.45193(8) 0.37856(9) 0.0218(2) Uani 1 1 d . . . . .
C3 C 0.47087(6) 0.59387(11) 0.15616(12) 0.0289(3) Uani 1 1 d . . . . .
H3 H 0.460621 0.569294 0.063373 0.035 Uiso 1 1 calc R U . . .
C4 C 0.43360(5) 0.67651(10) 0.21577(12) 0.0266(2) Uani 1 1 d . . . . .
H4 H 0.398216 0.709110 0.163439 0.032 Uiso 1 1 calc R U . . .
C5 C 0.44827(5) 0.71114(10) 0.35180(12) 0.0252(2) Uani 1 1 d . . . . .
H5 H 0.422777 0.767377 0.392648 0.030 Uiso 1 1 calc R U . . .
C6 C 0.50011(5) 0.66391(10) 0.42867(12) 0.0231(2) Uani 1 1 d . . . . .
H6 H 0.509692 0.687320 0.522113 0.028 Uiso 1 1 calc R U . . .
C7 C 0.59450(5) 0.53029(9) 0.44660(11) 0.0197(2) Uani 1 1 d . . . . .
C8 C 0.69773(5) 0.44671(9) 0.58509(11) 0.0187(2) Uani 1 1 d . . . . .
C9 C 0.68012(5) 0.40888(9) 0.44966(11) 0.0197(2) Uani 1 1 d . . . . .
C10 C 0.67511(5) 0.56139(9) 0.78299(11) 0.0195(2) Uani 1 1 d . . . . .
C11 C 0.73208(5) 0.52379(9) 0.84937(11) 0.0194(2) Uani 1 1 d . . . . .
C12 C 0.75278(5) 0.40682(9) 0.65694(10) 0.0186(2) Uani 1 1 d . . . . .
C13 C 0.63449(5) 0.63196(10) 0.85503(12) 0.0228(2) Uani 1 1 d . . . . .
H13 H 0.596359 0.660633 0.809716 0.027 Uiso 1 1 calc R U . . .
C14 C 0.65069(5) 0.65861(10) 0.99107(12) 0.0243(2) Uani 1 1 d . . . . .
H14 H 0.622431 0.703143 1.040783 0.029 Uiso 1 1 calc R U . . .
C15 C 0.70851(5) 0.62149(10) 1.05958(11) 0.0230(2) Uani 1 1 d . . . . .
C16 C 0.75304(5) 0.56009(9) 0.98456(11) 0.0202(2) Uani 1 1 d . . . . .
C17 C 0.71943(5) 0.32845(10) 0.38927(11) 0.0225(2) Uani 1 1 d . . . . .
H17 H 0.708692 0.301124 0.297779 0.027 Uiso 1 1 calc R U . . .
C18 C 0.79124(5) 0.32786(9) 0.59705(11) 0.0205(2) Uani 1 1 d . . . . .
H18 H 0.828815 0.300548 0.646112 0.025 Uiso 1 1 calc R U . . .
C19 C 0.77369(5) 0.28895(10) 0.46259(11) 0.0222(2) Uani 1 1 d . . . . .
H19 H 0.799633 0.234126 0.420655 0.027 Uiso 1 1 calc R U . . .
C20 C 0.72075(6) 0.63565(10) 1.20590(12) 0.0265(2) Uani 1 1 d . . . . .
H20 H 0.693566 0.682695 1.255479 0.032 Uiso 1 1 calc R U . . .
C21 C 0.81340(5) 0.52553(9) 1.05491(11) 0.0208(2) Uani 1 1 d . . . . .
C22 C 0.81690(5) 0.52269(10) 1.20161(11) 0.0240(2) Uani 1 1 d . . . . .
C23 C 0.77076(6) 0.58253(10) 1.27433(11) 0.0267(2) Uani 1 1 d . . . . .
H23 H 0.775325 0.585025 1.372691 0.032 Uiso 1 1 calc R U . . .
C24 C 0.86863(5) 0.49020(9) 0.98855(11) 0.0204(2) Uani 1 1 d . . . . .
C25 C 0.91250(5) 0.41600(10) 1.06284(12) 0.0233(2) Uani 1 1 d . . . . .
C26 C 0.90891(5) 0.39926(10) 1.20734(12) 0.0265(2) Uani 1 1 d . . . . .
H26 H 0.936764 0.346141 1.256322 0.032 Uiso 1 1 calc R U . . .
C27 C 0.86601(6) 0.45855(11) 1.27572(11) 0.0271(3) Uani 1 1 d . . . . .
H27 H 0.868718 0.457333 1.374107 0.033 Uiso 1 1 calc R U . . .
C28 C 0.88475(5) 0.53217(9) 0.85429(11) 0.0204(2) Uani 1 1 d . . . . .
C29 C 0.93360(5) 0.47600(10) 0.78799(11) 0.0226(2) Uani 1 1 d . . . . .
C30 C 0.97012(5) 0.38664(10) 0.85955(12) 0.0255(2) Uani 1 1 d . . . . .
H30 H 1.000419 0.344442 0.812929 0.031 Uiso 1 1 calc R U . . .
C31 C 0.96164(5) 0.36210(10) 0.99322(12) 0.0262(2) Uani 1 1 d . . . . .
H31 H 0.988885 0.307874 1.042042 0.031 Uiso 1 1 calc R U . . .
C32 C 0.85716(5) 0.63284(10) 0.79036(11) 0.0221(2) Uani 1 1 d . . . . .
H32 H 0.826796 0.675374 0.836415 0.026 Uiso 1 1 calc R U . . .
C33 C 0.87327(5) 0.67063(10) 0.66303(12) 0.0252(2) Uani 1 1 d . . . . .
H33 H 0.854071 0.738570 0.622462 0.030 Uiso 1 1 calc R U . . .
C34 C 0.91798(5) 0.60909(11) 0.59289(12) 0.0263(2) Uani 1 1 d . . . . .
H34 H 0.927548 0.632878 0.503017 0.032 Uiso 1 1 calc R U . . .
C35 C 0.94777(5) 0.51424(11) 0.65520(12) 0.0259(2) Uani 1 1 d . . . . .
H35 H 0.978495 0.473544 0.608172 0.031 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 C12 1.3715(12) . ?
O1 C11 1.3773(12) . ?
N1 C7 1.3445(14) . ?
N1 N2 1.3617(12) . ?
C1 C2 1.3939(16) . ?
C1 C6 1.3983(15) . ?
C1 C7 1.4883(15) . ?
N2 C8 1.3874(13) . ?
N2 C10 1.4021(14) . ?
C2 C3 1.3855(16) . ?
C2 H2 0.9500 . ?
N3 C7 1.3368(14) . ?
N3 C9 1.3726(14) . ?
C3 C4 1.3918(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3870(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3904(15) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C12 1.3915(14) . ?
C8 C9 1.4031(15) . ?
C9 C17 1.4052(15) . ?
C10 C11 1.3948(15) . ?
C10 C13 1.4104(15) . ?
C11 C16 1.4112(15) . ?
C12 C18 1.3804(15) . ?
C13 C14 1.3690(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.4161(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.4271(15) . ?
C15 C20 1.4289(16) . ?
C16 C21 1.4600(15) . ?
C17 C19 1.3827(15) . ?
C17 H17 0.9500 . ?
C18 C19 1.3982(15) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C23 1.3528(18) . ?
C20 H20 0.9500 . ?
C21 C22 1.4169(15) . ?
C21 C24 1.4442(15) . ?
C22 C27 1.4242(17) . ?
C22 C23 1.4307(17) . ?
C23 H23 0.9500 . ?
C24 C25 1.4162(15) . ?
C24 C28 1.4536(15) . ?
C25 C26 1.4207(16) . ?
C25 C31 1.4310(16) . ?
C26 C27 1.3546(18) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C32 1.4151(15) . ?
C28 C29 1.4211(15) . ?
C29 C35 1.4145(16) . ?
C29 C30 1.4309(16) . ?
C30 C31 1.3512(17) . ?
C30 H30 0.9500 . ?
C31 H31 0.9500 . ?
C32 C33 1.3767(15) . ?
C32 H32 0.9500 . ?
C33 C34 1.4045(16) . ?
C33 H33 0.9500 . ?
C34 C35 1.3740(17) . ?
C34 H34 0.9500 . ?
C35 H35 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
C12 O1 C11 118.86(8) . . ?
C7 N1 N2 114.83(9) . . ?
C2 C1 C6 119.21(10) . . ?
C2 C1 C7 118.96(10) . . ?
C6 C1 C7 121.84(10) . . ?
N1 N2 C8 121.86(9) . . ?
N1 N2 C10 118.97(9) . . ?
C8 N2 C10 119.15(9) . . ?
C3 C2 C1 120.53(11) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C7 N3 C9 115.62(9) . . ?
C2 C3 C4 120.07(11) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.80(10) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.30(11) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.08(10) . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N3 C7 N1 128.74(10) . . ?
N3 C7 C1 116.30(9) . . ?
N1 C7 C1 114.96(9) . . ?
N2 C8 C12 120.41(9) . . ?
N2 C8 C9 118.53(9) . . ?
C12 C8 C9 121.06(10) . . ?
N3 C9 C8 120.34(10) . . ?
N3 C9 C17 121.67(10) . . ?
C8 C9 C17 117.97(10) . . ?
C11 C10 N2 118.71(9) . . ?
C11 C10 C13 119.70(10) . . ?
N2 C10 C13 121.57(10) . . ?
O1 C11 C10 121.77(9) . . ?
O1 C11 C16 115.87(9) . . ?
C10 C11 C16 122.28(10) . . ?
O1 C12 C18 118.44(9) . . ?
O1 C12 C8 120.85(9) . . ?
C18 C12 C8 120.71(10) . . ?
C14 C13 C10 119.18(10) . . ?
C14 C13 H13 120.4 . . ?
C10 C13 H13 120.4 . . ?
C13 C14 C15 121.68(10) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C16 119.93(10) . . ?
C14 C15 C20 120.78(10) . . ?
C16 C15 C20 119.07(10) . . ?
C11 C16 C15 116.40(10) . . ?
C11 C16 C21 123.56(10) . . ?
C15 C16 C21 119.56(10) . . ?
C19 C17 C9 120.21(10) . . ?
C19 C17 H17 119.9 . . ?
C9 C17 H17 119.9 . . ?
C12 C18 C19 118.54(10) . . ?
C12 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C17 C19 C18 121.50(10) . . ?
C17 C19 H19 119.2 . . ?
C18 C19 H19 119.2 . . ?
C23 C20 C15 120.48(11) . . ?
C23 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C22 C21 C24 117.49(10) . . ?
C22 C21 C16 116.51(10) . . ?
C24 C21 C16 125.96(9) . . ?
C21 C22 C27 119.57(11) . . ?
C21 C22 C23 120.03(11) . . ?
C27 C22 C23 120.39(10) . . ?
C20 C23 C22 121.35(10) . . ?
C20 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C25 C24 C21 118.07(10) . . ?
C25 C24 C28 117.32(10) . . ?
C21 C24 C28 124.46(10) . . ?
C24 C25 C26 119.68(10) . . ?
C24 C25 C31 119.87(10) . . ?
C26 C25 C31 120.41(10) . . ?
C27 C26 C25 120.43(11) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C22 120.67(10) . . ?
C26 C27 H27 119.7 . . ?
C22 C27 H27 119.7 . . ?
C32 C28 C29 117.74(10) . . ?
C32 C28 C24 122.78(10) . . ?
C29 C28 C24 119.30(10) . . ?
C35 C29 C28 119.26(10) . . ?
C35 C29 C30 120.96(10) . . ?
C28 C29 C30 119.67(10) . . ?
C31 C30 C29 120.21(10) . . ?
C31 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?
C30 C31 C25 121.44(10) . . ?
C30 C31 H31 119.3 . . ?
C25 C31 H31 119.3 . . ?
C33 C32 C28 121.58(10) . . ?
C33 C32 H32 119.2 . . ?
C28 C32 H32 119.2 . . ?
C32 C33 C34 120.24(11) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C35 C34 C33 119.52(10) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C29 121.30(10) . . ?
C34 C35 H35 119.3 . . ?
C29 C35 H35 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C8 2.27(14) . . . . ?
C7 N1 N2 C10 -179.48(9) . . . . ?
C6 C1 C2 C3 0.27(17) . . . . ?
C7 C1 C2 C3 -179.88(10) . . . . ?
C1 C2 C3 C4 0.56(18) . . . . ?
C2 C3 C4 C5 -0.78(18) . . . . ?
C3 C4 C5 C6 0.18(17) . . . . ?
C4 C5 C6 C1 0.66(17) . . . . ?
C2 C1 C6 C5 -0.88(16) . . . . ?
C7 C1 C6 C5 179.28(10) . . . . ?
C9 N3 C7 N1 -1.66(16) . . . . ?
C9 N3 C7 C1 177.22(9) . . . . ?
N2 N1 C7 N3 0.39(16) . . . . ?
N2 N1 C7 C1 -178.51(8) . . . . ?
C2 C1 C7 N3 -0.58(15) . . . . ?
C6 C1 C7 N3 179.27(10) . . . . ?
C2 C1 C7 N1 178.46(10) . . . . ?
C6 C1 C7 N1 -1.69(15) . . . . ?
N1 N2 C8 C12 176.49(9) . . . . ?
C10 N2 C8 C12 -1.75(15) . . . . ?
N1 N2 C8 C9 -3.46(15) . . . . ?
C10 N2 C8 C9 178.30(9) . . . . ?
C7 N3 C9 C8 0.33(15) . . . . ?
C7 N3 C9 C17 -178.19(10) . . . . ?
N2 C8 C9 N3 2.06(15) . . . . ?
C12 C8 C9 N3 -177.89(9) . . . . ?
N2 C8 C9 C17 -179.37(9) . . . . ?
C12 C8 C9 C17 0.68(15) . . . . ?
N1 N2 C10 C11 -173.62(9) . . . . ?
C8 N2 C10 C11 4.68(14) . . . . ?
N1 N2 C10 C13 7.98(15) . . . . ?
C8 N2 C10 C13 -173.72(9) . . . . ?
C12 O1 C11 C10 4.29(14) . . . . ?
C12 O1 C11 C16 -178.84(9) . . . . ?
N2 C10 C11 O1 -6.05(15) . . . . ?
C13 C10 C11 O1 172.37(9) . . . . ?
N2 C10 C11 C16 177.28(9) . . . . ?
C13 C10 C11 C16 -4.30(16) . . . . ?
C11 O1 C12 C18 179.38(9) . . . . ?
C11 O1 C12 C8 -1.19(14) . . . . ?
N2 C8 C12 O1 -0.03(15) . . . . ?
C9 C8 C12 O1 179.92(9) . . . . ?
N2 C8 C12 C18 179.40(9) . . . . ?
C9 C8 C12 C18 -0.66(16) . . . . ?
C11 C10 C13 C14 -2.52(16) . . . . ?
N2 C10 C13 C14 175.86(10) . . . . ?
C10 C13 C14 C15 2.86(17) . . . . ?
C13 C14 C15 C16 3.46(17) . . . . ?
C13 C14 C15 C20 -171.04(11) . . . . ?
O1 C11 C16 C15 -166.61(9) . . . . ?
C10 C11 C16 C15 10.25(15) . . . . ?
O1 C11 C16 C21 5.35(15) . . . . ?
C10 C11 C16 C21 -177.79(10) . . . . ?
C14 C15 C16 C11 -9.71(15) . . . . ?
C20 C15 C16 C11 164.88(10) . . . . ?
C14 C15 C16 C21 177.99(10) . . . . ?
C20 C15 C16 C21 -7.42(15) . . . . ?
N3 C9 C17 C19 178.43(10) . . . . ?
C8 C9 C17 C19 -0.12(16) . . . . ?
O1 C12 C18 C19 179.49(9) . . . . ?
C8 C12 C18 C19 0.06(16) . . . . ?
C9 C17 C19 C18 -0.47(17) . . . . ?
C12 C18 C19 C17 0.51(17) . . . . ?
C14 C15 C20 C23 168.47(11) . . . . ?
C16 C15 C20 C23 -6.07(16) . . . . ?
C11 C16 C21 C22 -152.84(10) . . . . ?
C15 C16 C21 C22 18.88(14) . . . . ?
C11 C16 C21 C24 24.76(17) . . . . ?
C15 C16 C21 C24 -163.51(10) . . . . ?
C24 C21 C22 C27 -16.35(15) . . . . ?
C16 C21 C22 C27 161.46(10) . . . . ?
C24 C21 C22 C23 164.58(10) . . . . ?
C16 C21 C22 C23 -17.60(15) . . . . ?
C15 C20 C23 C22 7.61(17) . . . . ?
C21 C22 C23 C20 4.73(17) . . . . ?
C27 C22 C23 C20 -174.33(11) . . . . ?
C22 C21 C24 C25 23.30(14) . . . . ?
C16 C21 C24 C25 -154.28(10) . . . . ?
C22 C21 C24 C28 -152.08(10) . . . . ?
C16 C21 C24 C28 30.33(16) . . . . ?
C21 C24 C25 C26 -13.70(15) . . . . ?
C28 C24 C25 C26 162.01(10) . . . . ?
C21 C24 C25 C31 168.78(10) . . . . ?
C28 C24 C25 C31 -15.50(15) . . . . ?
C24 C25 C26 C27 -3.55(16) . . . . ?
C31 C25 C26 C27 173.95(11) . . . . ?
C25 C26 C27 C22 10.98(17) . . . . ?
C21 C22 C27 C26 -0.75(16) . . . . ?
C23 C22 C27 C26 178.31(10) . . . . ?
C25 C24 C28 C32 -159.01(10) . . . . ?
C21 C24 C28 C32 16.41(16) . . . . ?
C25 C24 C28 C29 16.01(15) . . . . ?
C21 C24 C28 C29 -168.58(10) . . . . ?
C32 C28 C29 C35 -6.94(15) . . . . ?
C24 C28 C29 C35 177.80(10) . . . . ?
C32 C28 C29 C30 169.35(10) . . . . ?
C24 C28 C29 C30 -5.91(15) . . . . ?
C35 C29 C30 C31 170.99(11) . . . . ?
C28 C29 C30 C31 -5.24(16) . . . . ?
C29 C30 C31 C25 5.95(17) . . . . ?
C24 C25 C31 C30 4.75(17) . . . . ?
C26 C25 C31 C30 -172.75(11) . . . . ?
C29 C28 C32 C33 4.95(16) . . . . ?
C24 C28 C32 C33 -179.96(10) . . . . ?
C28 C32 C33 C34 0.09(17) . . . . ?
C32 C33 C34 C35 -3.16(17) . . . . ?
C33 C34 C35 C29 1.02(17) . . . . ?
C28 C29 C35 C34 4.10(17) . . . . ?
C30 C29 C35 C34 -172.14(11) . . . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.042



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane aand acetonitrile mixture'
