# Electronic Supplementary Material (ESI) for Green 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. 
# 
#######################################################################

data_md_hc11
_database_code_depnum_ccdc_archive 'CCDC 2307938'
loop_
_audit_author_name
_audit_author_address
'Meitian Fu'
;Yunnan Minzu University
China
;
_audit_update_record             
;
2023-11-14 deposited with the CCDC.	2024-07-03 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            md_hc11
_chemical_formula_moiety         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         304.34
_chemical_absolute_configuration unk

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.3522(7)
_cell_length_b                   10.6585(10)
_cell_length_c                   10.8591(10)
_cell_angle_alpha                103.317(3)
_cell_angle_beta                 104.368(4)
_cell_angle_gamma                104.813(3)
_cell_volume                     756.72(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9979
_cell_measurement_theta_min      4.5192
_cell_measurement_theta_max      72.9259
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.680
_exptl_crystal_size_mid          0.440
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320

_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.26
_exptl_absorpt_correction_T_max  0.87

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            14697
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_theta_min         4.52
_diffrn_reflns_theta_max         73.92
_diffrn_reflns_theta_full        73.92
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measured_fraction_theta_full 0.912
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;

Refined as a 2-component twin.
;

_reflns_number_total             4658
_reflns_number_gt                3678
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2791
_refine_ls_R_factor_gt           0.2662
_refine_ls_wR_factor_gt          0.5610
_refine_ls_wR_factor_ref         0.5743
_refine_ls_goodness_of_fit_ref   2.665
_refine_ls_restrained_S_all      2.664
_refine_ls_number_reflns         4658
_refine_ls_number_parameters     418
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.173
_refine_ls_shift/su_mean         0.035
_refine_diff_density_max         0.854
_refine_diff_density_min         -0.869
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 945 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(6)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O2 0.8590(19) 0.7721(13) 0.4447(11) 0.050(3) Uani d . . . 1 . .
N N2 1.099(2) 0.9985(14) 0.4023(13) 0.041(3) Uani d . . . 1 . .
C C2 1.122(3) 0.9659(16) -0.2496(16) 0.046(4) Uani d . . . 1 . .
H H2 1.127826 0.962946 -0.33659 0.055 Uiso calc U . R 1 . .
O O1 0.7482(17) 0.6653(11) 0.2262(11) 0.042(2) Uani d . . . 1 . .
N N1 1.214(2) 1.0937(13) 0.2450(13) 0.040(3) Uani d . . . 1 . .
C C1 0.959(3) 0.8764(17) -0.2338(17) 0.052(4) Uani d . . . 1 . .
H H1 0.851888 0.814147 -0.310238 0.062 Uiso calc U . R 1 . .
O O4 0.586(2) 0.9634(11) 0.5694(10) 0.047(3) Uani d . . . 1 . .
N N4 0.240(2) 0.6319(14) 0.3940(13) 0.043(3) Uani d . . . 1 . .
C C4 1.255(2) 1.0639(18) -0.0112(15) 0.046(4) Uani d . . . 1 . .
H H4 1.357097 1.130846 0.065188 0.055 Uiso calc U . R 1 . .
C C3 1.271(3) 1.0570(17) -0.1390(16) 0.046(4) Uani d . . . 1 . .
H H3 1.385557 1.115431 -0.147981 0.055 Uiso calc U . R 1 . .
N N3 0.118(2) 0.5363(13) 0.5487(12) 0.041(3) Uani d . . . 1 . .
O O3 0.465(2) 0.8525(12) 0.3448(10) 0.051(3) Uani d . . . 1 . .
C C7 1.097(2) 0.9788(17) 0.1436(15) 0.040(3) Uani d . . . 1 . .
C C6 0.954(2) 0.8790(14) -0.1087(13) 0.040(3) Uani d . . . 1 . .
H H6 0.848813 0.811825 -0.099855 0.048 Uiso calc U . R 1 . .
C C5 1.096(2) 0.9760(15) 0.0065(13) 0.036(3) Uani d . . . 1 . .
C C8 0.972(2) 0.8724(16) 0.1659(14) 0.040(3) Uani d . . . 1 . .
H H8 0.882643 0.793869 0.094092 0.048 Uiso calc U . R 1 . .
C C9 0.980(2) 0.8845(16) 0.2971(15) 0.038(3) Uani d . . . 1 . .
C C01A -0.125(3) 0.2946(14) 0.3384(15) 0.045(4) Uani d . . . 1 . .
H H01A -0.141743 0.308256 0.424059 0.054 Uiso calc U . R 1 . .
C C19 1.312(2) 1.2478(18) 0.6027(16) 0.046(4) Uani d . . . 1 . .
H H19 1.221058 1.176654 0.618057 0.055 Uiso calc U . R 1 . .
C C20 0.068(3) 0.5583(14) 0.8015(14) 0.045(4) Uani d . . . 1 . .
H H20 -0.034369 0.491049 0.725772 0.054 Uiso calc U . R 1 . .
C C21 0.226(3) 0.6565(15) 0.7866(17) 0.045(4) Uani d . . . 1 . .
C C22 0.069(3) 0.5639(17) 0.9297(16) 0.052(4) Uani d . . . 1 . .
H H22 -0.035046 0.498903 0.941924 0.062 Uiso calc U . R 1 . .
C C23 0.219(3) 0.6629(17) 1.0429(14) 0.047(4) Uani d . . . 1 . .
H H23 0.214497 0.665523 1.130138 0.057 Uiso calc U . R 1 . .
C C24 0.373(2) 0.7566(16) 1.0263(15) 0.044(4) Uani d . . . 1 . .
H H24 0.47196 0.825333 1.102557 0.052 Uiso calc U . R 1 . .
C C25 0.383(3) 0.7509(18) 0.8976(17) 0.048(4) Uani d . . . 1 . .
H H25 0.494862 0.809639 0.886319 0.057 Uiso calc U . R 1 . .
C C26 0.023(3) 0.3807(15) 0.1844(15) 0.046(4) Uani d . . . 1 . .
H H26 0.107187 0.451403 0.164102 0.055 Uiso calc U . R 1 . .
C C27 -0.088(3) 0.2525(19) 0.0866(16) 0.056(4) Uani d . . . 1 . .
H H27 -0.070737 0.236039 0.001257 0.067 Uiso calc U . R 1 . .
C C28 -0.218(3) 0.1524(18) 0.1082(16) 0.049(4) Uani d . . . 1 . .
H H28 -0.299425 0.071036 0.037055 0.059 Uiso calc U . R 1 . .
C C29 -0.232(3) 0.1702(14) 0.2396(14) 0.046(4) Uani d . . . 1 . .
H H29 -0.31313 0.097601 0.259027 0.055 Uiso calc U . R 1 . .
C C30 0.005(3) 0.4004(18) 0.3155(14) 0.043(4) Uani d . . . 1 . .
C C31 0.347(3) 0.7440(17) 0.4938(15) 0.043(4) Uani d . . . 1 . .
C C32 0.475(3) 0.8562(15) 0.4609(13) 0.038(3) Uani d . . . 1 . .
C C33 0.236(3) 0.6489(14) 0.6502(15) 0.046(4) Uani d . . . 1 . .
C C35 0.128(2) 0.5307(15) 0.4242(13) 0.038(3) Uani d . . . 1 . .
C C34 0.350(3) 0.7625(14) 0.6242(15) 0.040(3) Uani d . . . 1 . .
H H34 0.425722 0.84675 0.693026 0.048 Uiso calc U . R 1 . .
C C36 0.718(3) 1.0768(17) 0.5495(19) 0.047(4) Uani d . . . 1 . .
H H36A 0.641281 1.112767 0.485948 0.057 Uiso calc U . R 1 . .
H H36B 0.815491 1.047095 0.512336 0.057 Uiso calc U . R 1 . .
C C37 0.825(3) 1.187(2) 0.685(2) 0.064(6) Uani d . . . 1 . .
H H37A 0.930742 1.258872 0.677227 0.096 Uiso calc U . R 1 . .
H H37B 0.882562 1.146445 0.750677 0.096 Uiso calc U . R 1 . .
H H37C 0.729638 1.225944 0.714002 0.096 Uiso calc U . R 1 . .
C C10 0.863(3) 0.7667(18) 0.3382(17) 0.048(4) Uani d . . . 1 . .
C C12 0.514(3) 0.4430(16) 0.1134(17) 0.050(4) Uani d . . . 1 . .
H H12A 0.414046 0.36612 0.120007 0.075 Uiso calc U . R 1 . .
H H12B 0.615273 0.411131 0.085141 0.075 Uiso calc U . R 1 . .
H H12C 0.449299 0.480718 0.047517 0.075 Uiso calc U . R 1 . .
C C11 0.609(3) 0.5508(15) 0.2464(17) 0.041(3) Uani d . . . 1 . .
H H11A 0.508022 0.580695 0.2787 0.05 Uiso calc U . R 1 . .
H H11B 0.682256 0.516 0.313 0.05 Uiso calc U . R 1 . .
C C15 1.455(2) 1.3355(16) 0.4529(16) 0.044(4) Uani d . . . 1 . .
H H15 1.461497 1.32687 0.365236 0.053 Uiso calc U . R 1 . .
C C14 1.327(2) 1.2283(15) 0.4784(15) 0.039(3) Uani d . . . 1 . .
C C13 1.207(2) 1.1002(16) 0.3661(15) 0.039(3) Uani d . . . 1 . .
C C17 1.552(2) 1.4717(16) 0.6816(15) 0.043(3) Uani d . . . 1 . .
H H17 1.626926 1.555269 0.751381 0.052 Uiso calc U . R 1 . .
C C16 1.572(3) 1.4555(18) 0.560(2) 0.053(4) Uani d . . . 1 . .
H H16 1.665649 1.525773 0.545493 0.063 Uiso calc U . R 1 . .
C C18 1.421(3) 1.3654(16) 0.7074(15) 0.044(3) Uani d . . . 1 . .
H H18 1.408393 1.375266 0.793908 0.053 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O2 C10 . 1.15(2) ?
N2 C9 . 1.367(18) ?
N2 C13 . 1.37(2) ?
C2 C3 . 1.36(2) ?
C2 C1 . 1.40(3) ?
C2 H2 . 0.95 ?
O1 C10 . 1.334(19) ?
O1 C11 . 1.475(15) ?
N1 C13 . 1.314(19) ?
N1 C7 . 1.349(19) ?
C1 C6 . 1.36(2) ?
C1 H1 . 0.95 ?
O4 C32 . 1.336(17) ?
O4 C36 . 1.441(18) ?
N4 C31 . 1.31(2) ?
N4 C35 . 1.337(19) ?
C4 C5 . 1.388(19) ?
C4 C3 . 1.41(2) ?
C4 H4 . 0.95 ?
C3 H3 . 0.95 ?
N3 C33 . 1.34(2) ?
N3 C35 . 1.361(16) ?
O3 C32 . 1.236(16) ?
C7 C8 . 1.38(2) ?
C7 C5 . 1.480(18) ?
C6 C5 . 1.388(17) ?
C6 H6 . 0.95 ?
C8 C9 . 1.38(2) ?
C8 H8 . 0.95 ?
C9 C10 . 1.55(2) ?
C01A C29 . 1.385(18) ?
C01A C30 . 1.40(2) ?
C01A H01A . 0.95 ?
C19 C14 . 1.35(2) ?
C19 C18 . 1.37(2) ?
C19 H19 . 0.95 ?
C20 C22 . 1.378(19) ?
C20 C21 . 1.420(18) ?
C20 H20 . 0.95 ?
C21 C25 . 1.40(2) ?
C21 C33 . 1.487(18) ?
C22 C23 . 1.41(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.384(19) ?
C23 H23 . 0.95 ?
C24 C25 . 1.41(2) ?
C24 H24 . 0.95 ?
C25 H25 . 0.95 ?
C26 C27 . 1.41(2) ?
C26 C30 . 1.435(19) ?
C26 H26 . 0.95 ?
C27 C28 . 1.35(3) ?
C27 H27 . 0.95 ?
C28 C29 . 1.43(2) ?
C28 H28 . 0.95 ?
C29 H29 . 0.95 ?
C30 C35 . 1.487(19) ?
C31 C34 . 1.38(2) ?
C31 C32 . 1.496(18) ?
C33 C34 . 1.417(17) ?
C34 H34 . 0.95 ?
C36 C37 . 1.52(2) ?
C36 H36A . 0.99 ?
C36 H36B . 0.99 ?
C37 H37A . 0.98 ?
C37 H37B . 0.98 ?
C37 H37C . 0.98 ?
C12 C11 . 1.49(2) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C15 C16 . 1.41(2) ?
C15 C14 . 1.411(17) ?
C15 H15 . 0.95 ?
C14 C13 . 1.49(2) ?
C17 C16 . 1.34(3) ?
C17 C18 . 1.42(2) ?
C17 H17 . 0.95 ?
C16 H16 . 0.95 ?
C18 H18 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 N2 C13 . . 113.9(13) ?
C3 C2 C1 . . 119.3(13) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C10 O1 C11 . . 114.6(12) ?
C13 N1 C7 . . 118.1(13) ?
C6 C1 C2 . . 119.9(16) ?
C6 C1 H1 . . 120.0 ?
C2 C1 H1 . . 120.0 ?
C32 O4 C36 . . 116.9(11) ?
C31 N4 C35 . . 116.2(12) ?
C5 C4 C3 . . 122.0(13) ?
C5 C4 H4 . . 119.0 ?
C3 C4 H4 . . 119.0 ?
C2 C3 C4 . . 119.4(12) ?
C2 C3 H3 . . 120.3 ?
C4 C3 H3 . . 120.3 ?
C33 N3 C35 . . 117.7(12) ?
N1 C7 C8 . . 121.0(12) ?
N1 C7 C5 . . 117.7(13) ?
C8 C7 C5 . . 121.2(13) ?
C1 C6 C5 . . 122.6(14) ?
C1 C6 H6 . . 118.7 ?
C5 C6 H6 . . 118.7 ?
C4 C5 C6 . . 116.4(12) ?
C4 C5 C7 . . 119.5(12) ?
C6 C5 C7 . . 123.7(12) ?
C7 C8 C9 . . 117.4(14) ?
C7 C8 H8 . . 121.3 ?
C9 C8 H8 . . 121.3 ?
N2 C9 C8 . . 123.0(14) ?
N2 C9 C10 . . 114.1(13) ?
C8 C9 C10 . . 122.8(13) ?
C29 C01A C30 . . 121.8(13) ?
C29 C01A H01A . . 119.1 ?
C30 C01A H01A . . 119.1 ?
C14 C19 C18 . . 123.2(13) ?
C14 C19 H19 . . 118.4 ?
C18 C19 H19 . . 118.4 ?
C22 C20 C21 . . 117.7(14) ?
C22 C20 H20 . . 121.2 ?
C21 C20 H20 . . 121.2 ?
C25 C21 C20 . . 121.5(13) ?
C25 C21 C33 . . 118.9(13) ?
C20 C21 C33 . . 119.2(14) ?
C20 C22 C23 . . 121.9(14) ?
C20 C22 H22 . . 119.1 ?
C23 C22 H22 . . 119.0 ?
C24 C23 C22 . . 119.5(13) ?
C24 C23 H23 . . 120.2 ?
C22 C23 H23 . . 120.2 ?
C23 C24 C25 . . 120.6(14) ?
C23 C24 H24 . . 119.7 ?
C25 C24 H24 . . 119.7 ?
C21 C25 C24 . . 118.4(12) ?
C21 C25 H25 . . 120.8 ?
C24 C25 H25 . . 120.8 ?
C27 C26 C30 . . 117.5(14) ?
C27 C26 H26 . . 121.2 ?
C30 C26 H26 . . 121.2 ?
C28 C27 C26 . . 123.4(14) ?
C28 C27 H27 . . 118.3 ?
C26 C27 H27 . . 118.4 ?
C27 C28 C29 . . 119.0(14) ?
C27 C28 H28 . . 120.5 ?
C29 C28 H28 . . 120.5 ?
C01A C29 C28 . . 119.3(14) ?
C01A C29 H29 . . 120.4 ?
C28 C29 H29 . . 120.3 ?
C01A C30 C26 . . 118.7(13) ?
C01A C30 C35 . . 121.6(12) ?
C26 C30 C35 . . 119.7(14) ?
N4 C31 C34 . . 124.5(13) ?
N4 C31 C32 . . 116.3(11) ?
C34 C31 C32 . . 119.1(14) ?
O3 C32 O4 . . 124.8(13) ?
O3 C32 C31 . . 122.7(14) ?
O4 C32 C31 . . 112.2(11) ?
N3 C33 C34 . . 120.0(13) ?
N3 C33 C21 . . 118.2(11) ?
C34 C33 C21 . . 121.5(13) ?
N4 C35 N3 . . 125.0(13) ?
N4 C35 C30 . . 118.8(12) ?
N3 C35 C30 . . 116.2(12) ?
C31 C34 C33 . . 116.3(14) ?
C31 C34 H34 . . 121.8 ?
C33 C34 H34 . . 121.9 ?
O4 C36 C37 . . 107.7(14) ?
O4 C36 H36A . . 110.2 ?
C37 C36 H36A . . 110.2 ?
O4 C36 H36B . . 110.2 ?
C37 C36 H36B . . 110.2 ?
H36A C36 H36B . . 108.5 ?
C36 C37 H37A . . 109.5 ?
C36 C37 H37B . . 109.5 ?
H37A C37 H37B . . 109.5 ?
C36 C37 H37C . . 109.5 ?
H37A C37 H37C . . 109.5 ?
H37B C37 H37C . . 109.5 ?
O2 C10 O1 . . 125.9(17) ?
O2 C10 C9 . . 126.0(14) ?
O1 C10 C9 . . 107.6(14) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.4 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O1 C11 C12 . . 106.0(12) ?
O1 C11 H11A . . 110.5 ?
C12 C11 H11A . . 110.5 ?
O1 C11 H11B . . 110.5 ?
C12 C11 H11B . . 110.6 ?
H11A C11 H11B . . 108.7 ?
C16 C15 C14 . . 118.7(13) ?
C16 C15 H15 . . 120.6 ?
C14 C15 H15 . . 120.6 ?
C19 C14 C15 . . 118.9(14) ?
C19 C14 C13 . . 122.4(11) ?
C15 C14 C13 . . 118.6(12) ?
N1 C13 N2 . . 126.4(15) ?
N1 C13 C14 . . 119.1(13) ?
N2 C13 C14 . . 114.4(12) ?
C16 C17 C18 . . 120.8(13) ?
C16 C17 H17 . . 119.6 ?
C18 C17 H17 . . 119.6 ?
C17 C16 C15 . . 120.6(14) ?
C17 C16 H16 . . 119.7 ?
C15 C16 H16 . . 119.7 ?
C19 C18 C17 . . 117.5(13) ?
C19 C18 H18 . . 121.2 ?
C17 C18 H18 . . 121.3 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C3 C2 C1 C6 . . . . -2.(3) ?
C1 C2 C3 C4 . . . . -3.(3) ?
C5 C4 C3 C2 . . . . 3.(3) ?
C13 N1 C7 C8 . . . . 1.(2) ?
C13 N1 C7 C5 . . . . 176.1(13) ?
C2 C1 C6 C5 . . . . 6.(3) ?
C3 C4 C5 C6 . . . . 1.(2) ?
C3 C4 C5 C7 . . . . 173.9(15) ?
C1 C6 C5 C4 . . . . -6.(2) ?
C1 C6 C5 C7 . . . . -178.2(15) ?
N1 C7 C5 C4 . . . . 22.(2) ?
C8 C7 C5 C4 . . . . -162.9(16) ?
N1 C7 C5 C6 . . . . -165.4(15) ?
C8 C7 C5 C6 . . . . 9.(2) ?
N1 C7 C8 C9 . . . . -4.(2) ?
C5 C7 C8 C9 . . . . -178.9(15) ?
C13 N2 C9 C8 . . . . 1.(2) ?
C13 N2 C9 C10 . . . . 177.8(15) ?
C7 C8 C9 N2 . . . . 3.(2) ?
C7 C8 C9 C10 . . . . -173.6(16) ?
C22 C20 C21 C25 . . . . 4.(3) ?
C22 C20 C21 C33 . . . . 176.7(16) ?
C21 C20 C22 C23 . . . . 0.(3) ?
C20 C22 C23 C24 . . . . -1.(3) ?
C22 C23 C24 C25 . . . . -2.(3) ?
C20 C21 C25 C24 . . . . -7.(3) ?
C33 C21 C25 C24 . . . . -179.6(16) ?
C23 C24 C25 C21 . . . . 6.(3) ?
C30 C26 C27 C28 . . . . 4.(3) ?
C26 C27 C28 C29 . . . . -6.(3) ?
C30 C01A C29 C28 . . . . -4.(3) ?
C27 C28 C29 C01A . . . . 6.(3) ?
C29 C01A C30 C26 . . . . 2.(3) ?
C29 C01A C30 C35 . . . . -176.3(17) ?
C27 C26 C30 C01A . . . . -2.(3) ?
C27 C26 C30 C35 . . . . 176.5(17) ?
C35 N4 C31 C34 . . . . 0.(3) ?
C35 N4 C31 C32 . . . . 178.6(17) ?
C36 O4 C32 O3 . . . . -7.(3) ?
C36 O4 C32 C31 . . . . 179.0(16) ?
N4 C31 C32 O3 . . . . 9.(3) ?
C34 C31 C32 O3 . . . . -172.8(18) ?
N4 C31 C32 O4 . . . . -176.9(15) ?
C34 C31 C32 O4 . . . . 2.(2) ?
C35 N3 C33 C34 . . . . 6.(3) ?
C35 N3 C33 C21 . . . . 179.8(16) ?
C25 C21 C33 N3 . . . . 161.3(18) ?
C20 C21 C33 N3 . . . . -12.(3) ?
C25 C21 C33 C34 . . . . -25.(3) ?
C20 C21 C33 C34 . . . . 161.4(17) ?
C31 N4 C35 N3 . . . . 0.(3) ?
C31 N4 C35 C30 . . . . -179.4(15) ?
C33 N3 C35 N4 . . . . -4.(3) ?
C33 N3 C35 C30 . . . . 176.0(15) ?
C01A C30 C35 N4 . . . . -175.2(17) ?
C26 C30 C35 N4 . . . . 6.(2) ?
C01A C30 C35 N3 . . . . 5.(2) ?
C26 C30 C35 N3 . . . . -173.5(16) ?
N4 C31 C34 C33 . . . . 3.(3) ?
C32 C31 C34 C33 . . . . -175.8(17) ?
N3 C33 C34 C31 . . . . -6.(3) ?
C21 C33 C34 C31 . . . . -179.1(17) ?
C32 O4 C36 C37 . . . . 179.0(16) ?
C11 O1 C10 O2 . . . . -1.(3) ?
C11 O1 C10 C9 . . . . -173.4(13) ?
N2 C9 C10 O2 . . . . 6.(3) ?
C8 C9 C10 O2 . . . . -177.(2) ?
N2 C9 C10 O1 . . . . 177.5(14) ?
C8 C9 C10 O1 . . . . -5.(2) ?
C10 O1 C11 C12 . . . . -173.6(16) ?
C18 C19 C14 C15 . . . . -3.(3) ?
C18 C19 C14 C13 . . . . -179.8(16) ?
C16 C15 C14 C19 . . . . 4.(3) ?
C16 C15 C14 C13 . . . . -178.5(16) ?
C7 N1 C13 N2 . . . . 3.(2) ?
C7 N1 C13 C14 . . . . -177.1(13) ?
C9 N2 C13 N1 . . . . -4.(2) ?
C9 N2 C13 C14 . . . . 176.2(12) ?
C19 C14 C13 N1 . . . . 172.9(17) ?
C15 C14 C13 N1 . . . . -4.(2) ?
C19 C14 C13 N2 . . . . -7.(2) ?
C15 C14 C13 N2 . . . . 175.5(16) ?
C18 C17 C16 C15 . . . . 3.(3) ?
C14 C15 C16 C17 . . . . -5.(3) ?
C14 C19 C18 C17 . . . . 1.(3) ?
C16 C17 C18 C19 . . . . -2.(3) ?



