# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_new
_database_code_depnum_ccdc_archive 'CCDC 994103'
_audit_update_record             
;
2014-03-27 deposited with the CCDC.	2022-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
_publ_contact_author_address
;
_chemical_name_common            Ibu-Pro-Val-OMe
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H52 N4 O8'
_chemical_formula_sum            'C30 H52 N4 O8'
_chemical_formula_weight         596.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'

_cell_length_a                   8.900(2)
_cell_length_b                   8.958(2)
_cell_length_c                   10.397(2)
_cell_angle_alpha                92.153(13)
_cell_angle_beta                 96.035(13)
_cell_angle_gamma                94.714(12)
_cell_volume                     820.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             324
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD'
_diffrn_measurement_method       OMEGA
_diffrn_detector_area_resol_mean 0.3
_diffrn_reflns_number            12266
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0593
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5408
_reflns_number_gt                4838
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART APEX CCD'
_computing_cell_refinement       'BRUKER SMART APEX CCD'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ORTEP-III
_computing_publication_material  'WinGX v1.80.05'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(9)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         5408
_refine_ls_number_parameters     389
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1160
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_restrained_S_all      0.844
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.1289(2) 0.46178(19) 0.01930(17) 0.0243(4) Uani 1 1 d . . .
O2 O 1.1445(3) 0.6989(2) -0.0410(3) 0.0534(7) Uani 1 1 d . . .
O3 O 0.9058(2) 0.8137(2) 0.29424(16) 0.0266(4) Uani 1 1 d . . .
O4 O 0.6188(2) 1.17510(19) 0.35775(16) 0.0225(4) Uani 1 1 d . . .
O5 O 0.2000(2) 0.58084(19) 0.56684(19) 0.0257(4) Uani 1 1 d . . .
O6 O 0.1616(2) 0.33041(19) 0.56506(18) 0.0240(4) Uani 1 1 d . . .
O7 O 0.4453(2) 0.24469(19) 0.77566(16) 0.0216(4) Uani 1 1 d . . .
O8 O 0.7381(2) -0.1134(2) 0.85975(17) 0.0259(4) Uani 1 1 d . . .
N1 N 0.8062(2) 1.1031(2) 0.24771(19) 0.0183(4) Uani 1 1 d . . .
N2 N 0.8985(2) 0.7646(2) 0.07732(19) 0.0179(4) Uani 1 1 d . . .
H4 H 0.8757 0.7990 0.0023 0.022 Uiso 1 1 calc R . .
N3 N 0.5411(2) -0.0465(2) 0.72696(19) 0.0163(4) Uani 1 1 d . . .
N4 N 0.4644(2) 0.2966(2) 0.56554(19) 0.0167(4) Uani 1 1 d . . .
H30 H 0.4938 0.2654 0.4939 0.020 Uiso 1 1 calc R . .
C1 C 0.4594(3) 1.0888(3) 0.0853(2) 0.0267(6) Uani 1 1 d . . .
H9 H 0.4160 1.1673 0.1303 0.040 Uiso 1 1 calc R . .
H10 H 0.3801 1.0268 0.0342 0.040 Uiso 1 1 calc R . .
H1 H 0.5291 1.1319 0.0296 0.040 Uiso 1 1 calc R . .
C2 C 0.5440(3) 0.9930(3) 0.1839(2) 0.0196(5) Uani 1 1 d . . .
H8 H 0.5964 0.9192 0.1376 0.024 Uiso 1 1 calc R . .
C3 C 0.6594(3) 1.0949(3) 0.2699(2) 0.0169(5) Uani 1 1 d . . .
C4 C 0.8703(3) 1.0177(3) 0.1472(2) 0.0178(5) Uani 1 1 d . . .
H17 H 0.8101 1.0219 0.0631 0.021 Uiso 1 1 calc R . .
C5 C 0.8909(3) 0.8538(3) 0.1817(2) 0.0176(5) Uani 1 1 d . . .
C6 C 0.9433(3) 0.6126(3) 0.0839(2) 0.0164(5) Uani 1 1 d . . .
H25 H 0.9708 0.5936 0.1752 0.020 Uiso 1 1 calc R . .
C7 C 1.0833(3) 0.6005(3) 0.0139(3) 0.0221(6) Uani 1 1 d . . .
C8 C 1.2527(4) 0.4319(4) -0.0548(3) 0.0355(7) Uani 1 1 d . . .
H2 H 1.2238 0.4476 -0.1446 0.053 Uiso 1 1 calc R . .
H3 H 1.2761 0.3300 -0.0451 0.053 Uiso 1 1 calc R . .
H26 H 1.3402 0.4984 -0.0241 0.053 Uiso 1 1 calc R . .
C9 C 0.4323(3) 0.9111(3) 0.2647(3) 0.0306(6) Uani 1 1 d . . .
H6 H 0.4861 0.8502 0.3246 0.046 Uiso 1 1 calc R . .
H5 H 0.3583 0.8486 0.2086 0.046 Uiso 1 1 calc R . .
H7 H 0.3822 0.9831 0.3116 0.046 Uiso 1 1 calc R . .
C10 C 0.9199(3) 1.2081(3) 0.3234(2) 0.0226(6) Uani 1 1 d . . .
H12 H 0.9133 1.2004 0.4155 0.027 Uiso 1 1 calc R . .
H11 H 0.9075 1.3106 0.3004 0.027 Uiso 1 1 calc R . .
C11 C 1.0702(3) 1.1584(3) 0.2865(3) 0.0255(6) Uani 1 1 d . . .
H13 H 1.1477 1.2418 0.2935 0.031 Uiso 1 1 calc R . .
H14 H 1.1051 1.0796 0.3406 0.031 Uiso 1 1 calc R . .
C12 C 1.0299(3) 1.1012(3) 0.1467(3) 0.0221(6) Uani 1 1 d . . .
H15 H 1.1021 1.0335 0.1208 0.027 Uiso 1 1 calc R . .
H16 H 1.0270 1.1834 0.0887 0.027 Uiso 1 1 calc R . .
C13 C 0.8141(3) 0.4941(3) 0.0302(2) 0.0213(6) Uani 1 1 d . . .
H24 H 0.8511 0.3950 0.0423 0.026 Uiso 1 1 calc R . .
C14 C 0.7693(4) 0.5079(3) -0.1150(3) 0.0325(7) Uani 1 1 d . . .
H18 H 0.6910 0.4306 -0.1453 0.049 Uiso 1 1 calc R . .
H19 H 0.8561 0.4973 -0.1610 0.049 Uiso 1 1 calc R . .
H20 H 0.7326 0.6043 -0.1297 0.049 Uiso 1 1 calc R . .
C15 C 0.6789(3) 0.5039(3) 0.1064(3) 0.0348(7) Uani 1 1 d . . .
H23 H 0.6418 0.6011 0.0982 0.052 Uiso 1 1 calc R . .
H22 H 0.7089 0.4884 0.1960 0.052 Uiso 1 1 calc R . .
H21 H 0.6002 0.4282 0.0733 0.052 Uiso 1 1 calc R . .
C16 C 0.9272(3) 0.1361(3) 0.7938(3) 0.0291(6) Uani 1 1 d . . .
H38 H 0.8855 0.1973 0.8566 0.044 Uiso 1 1 calc R . .
H37 H 0.9948 0.1976 0.7477 0.044 Uiso 1 1 calc R . .
H27 H 0.9819 0.0610 0.8370 0.044 Uiso 1 1 calc R . .
C17 C 0.7993(3) 0.0605(3) 0.6989(2) 0.0179(5) Uani 1 1 d . . .
H39 H 0.7442 0.1370 0.6539 0.021 Uiso 1 1 calc R . .
C18 C 0.6907(3) -0.0378(3) 0.7693(2) 0.0178(5) Uani 1 1 d . . .
C19 C 0.4687(3) 0.0392(3) 0.6239(2) 0.0158(5) Uani 1 1 d . . .
H43 H 0.5191 0.0304 0.5449 0.019 Uiso 1 1 calc R . .
C20 C 0.4611(3) 0.2028(3) 0.6651(2) 0.0150(5) Uani 1 1 d . . .
C21 C 0.4195(3) 0.4482(3) 0.5772(2) 0.0153(5) Uani 1 1 d . . .
H44 H 0.4614 0.4910 0.6629 0.018 Uiso 1 1 calc R . .
C22 C 0.2461(3) 0.4425(3) 0.5702(2) 0.0162(5) Uani 1 1 d . . .
C23 C 0.0368(3) 0.5907(3) 0.5519(3) 0.0310(7) Uani 1 1 d . . .
H52 H -0.0099 0.5183 0.4863 0.047 Uiso 1 1 calc R . .
H29 H 0.0154 0.6895 0.5270 0.047 Uiso 1 1 calc R . .
H28 H -0.0028 0.5708 0.6325 0.047 Uiso 1 1 calc R . .
C24 C 0.4312(3) -0.1460(3) 0.7871(2) 0.0202(5) Uani 1 1 d . . .
H31 H 0.4483 -0.1354 0.8808 0.024 Uiso 1 1 calc R . .
H32 H 0.4370 -0.2501 0.7602 0.024 Uiso 1 1 calc R . .
C25 C 0.2785(3) -0.0916(3) 0.7368(3) 0.0220(5) Uani 1 1 d . . .
H35 H 0.1985 -0.1727 0.7308 0.026 Uiso 1 1 calc R . .
H36 H 0.2521 -0.0107 0.7924 0.026 Uiso 1 1 calc R . .
C26 C 0.3049(3) -0.0371(3) 0.6031(2) 0.0199(5) Uani 1 1 d . . .
H33 H 0.2329 0.0338 0.5749 0.024 Uiso 1 1 calc R . .
H34 H 0.2966 -0.1204 0.5395 0.024 Uiso 1 1 calc R . .
C27 C 0.8616(3) -0.0415(3) 0.6002(3) 0.0300(7) Uani 1 1 d . . .
H42 H 0.9052 -0.1231 0.6434 0.045 Uiso 1 1 calc R . .
H41 H 0.9381 0.0147 0.5590 0.045 Uiso 1 1 calc R . .
H40 H 0.7808 -0.0802 0.5362 0.045 Uiso 1 1 calc R . .
C28 C 0.4816(3) 0.5492(3) 0.4754(2) 0.0179(5) Uani 1 1 d . . .
H45 H 0.4522 0.6503 0.4933 0.022 Uiso 1 1 calc R . .
C29 C 0.4136(3) 0.5006(3) 0.3387(2) 0.0210(5) Uani 1 1 d . . .
H47 H 0.4410 0.4020 0.3175 0.032 Uiso 1 1 calc R . .
H46 H 0.4516 0.5697 0.2789 0.032 Uiso 1 1 calc R . .
H48 H 0.3052 0.4995 0.3332 0.032 Uiso 1 1 calc R . .
C30 C 0.6562(3) 0.5590(3) 0.4895(3) 0.0246(6) Uani 1 1 d . . .
H49 H 0.6892 0.4617 0.4717 0.037 Uiso 1 1 calc R . .
H50 H 0.6947 0.5934 0.5761 0.037 Uiso 1 1 calc R . .
H51 H 0.6935 0.6280 0.4294 0.037 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.340(3) . ?
O1 C8 1.445(3) . ?
O2 C7 1.194(3) . ?
O3 C5 1.234(3) . ?
O4 C3 1.243(3) . ?
O5 C22 1.337(3) . ?
O5 C23 1.455(3) . ?
O6 C22 1.201(3) . ?
O7 C20 1.222(3) . ?
O8 C18 1.238(3) . ?
N1 C3 1.347(3) . ?
N1 C4 1.463(3) . ?
N1 C10 1.466(3) . ?
N2 C5 1.333(3) . ?
N2 C6 1.452(3) . ?
N2 H4 0.8600 . ?
N3 C18 1.353(3) . ?
N3 C19 1.466(3) . ?
N3 C24 1.473(3) . ?
N4 C20 1.359(3) . ?
N4 C21 1.451(3) . ?
N4 H30 0.8600 . ?
C1 C2 1.538(4) . ?
C1 H9 0.9600 . ?
C1 H10 0.9600 . ?
C1 H1 0.9600 . ?
C2 C3 1.509(4) . ?
C2 C9 1.528(4) . ?
C2 H8 0.9800 . ?
C4 C5 1.546(3) . ?
C4 C12 1.550(4) . ?
C4 H17 0.9800 . ?
C6 C7 1.516(3) . ?
C6 C13 1.543(4) . ?
C6 H25 0.9800 . ?
C8 H2 0.9600 . ?
C8 H3 0.9600 . ?
C8 H26 0.9600 . ?
C9 H6 0.9600 . ?
C9 H5 0.9600 . ?
C9 H7 0.9600 . ?
C10 C11 1.525(4) . ?
C10 H12 0.9700 . ?
C10 H11 0.9700 . ?
C11 C12 1.520(4) . ?
C11 H13 0.9700 . ?
C11 H14 0.9700 . ?
C12 H15 0.9700 . ?
C12 H16 0.9700 . ?
C13 C15 1.515(4) . ?
C13 C14 1.533(4) . ?
C13 H24 0.9800 . ?
C14 H18 0.9600 . ?
C14 H19 0.9600 . ?
C14 H20 0.9600 . ?
C15 H23 0.9600 . ?
C15 H22 0.9600 . ?
C15 H21 0.9600 . ?
C16 C17 1.521(4) . ?
C16 H38 0.9600 . ?
C16 H37 0.9600 . ?
C16 H27 0.9600 . ?
C17 C18 1.517(3) . ?
C17 C27 1.526(3) . ?
C17 H39 0.9800 . ?
C19 C20 1.520(3) . ?
C19 C26 1.549(4) . ?
C19 H43 0.9800 . ?
C21 C22 1.533(3) . ?
C21 C28 1.535(3) . ?
C21 H44 0.9800 . ?
C23 H52 0.9600 . ?
C23 H29 0.9600 . ?
C23 H28 0.9600 . ?
C24 C25 1.528(4) . ?
C24 H31 0.9700 . ?
C24 H32 0.9700 . ?
C25 C26 1.525(4) . ?
C25 H35 0.9700 . ?
C25 H36 0.9700 . ?
C26 H33 0.9700 . ?
C26 H34 0.9700 . ?
C27 H42 0.9600 . ?
C27 H41 0.9600 . ?
C27 H40 0.9600 . ?
C28 C29 1.518(4) . ?
C28 C30 1.540(4) . ?
C28 H45 0.9800 . ?
C29 H47 0.9600 . ?
C29 H46 0.9600 . ?
C29 H48 0.9600 . ?
C30 H49 0.9600 . ?
C30 H50 0.9600 . ?
C30 H51 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 C8 116.0(2) . . ?
C22 O5 C23 116.1(2) . . ?
C3 N1 C4 126.2(2) . . ?
C3 N1 C10 121.3(2) . . ?
C4 N1 C10 112.53(19) . . ?
C5 N2 C6 123.4(2) . . ?
C5 N2 H4 118.3 . . ?
C6 N2 H4 118.3 . . ?
C18 N3 C19 126.46(19) . . ?
C18 N3 C24 120.9(2) . . ?
C19 N3 C24 112.66(19) . . ?
C20 N4 C21 121.64(18) . . ?
C20 N4 H30 119.2 . . ?
C21 N4 H30 119.2 . . ?
C2 C1 H9 109.5 . . ?
C2 C1 H10 109.5 . . ?
H9 C1 H10 109.5 . . ?
C2 C1 H1 109.5 . . ?
H9 C1 H1 109.5 . . ?
H10 C1 H1 109.5 . . ?
C3 C2 C9 110.4(2) . . ?
C3 C2 C1 108.5(2) . . ?
C9 C2 C1 110.3(2) . . ?
C3 C2 H8 109.2 . . ?
C9 C2 H8 109.2 . . ?
C1 C2 H8 109.2 . . ?
O4 C3 N1 119.9(2) . . ?
O4 C3 C2 120.3(2) . . ?
N1 C3 C2 119.7(2) . . ?
N1 C4 C5 113.02(19) . . ?
N1 C4 C12 102.33(19) . . ?
C5 C4 C12 108.1(2) . . ?
N1 C4 H17 111.0 . . ?
C5 C4 H17 111.0 . . ?
C12 C4 H17 111.0 . . ?
O3 C5 N2 124.7(2) . . ?
O3 C5 C4 122.8(2) . . ?
N2 C5 C4 112.4(2) . . ?
N2 C6 C7 109.16(19) . . ?
N2 C6 C13 112.6(2) . . ?
C7 C6 C13 111.5(2) . . ?
N2 C6 H25 107.8 . . ?
C7 C6 H25 107.8 . . ?
C13 C6 H25 107.8 . . ?
O2 C7 O1 123.7(2) . . ?
O2 C7 C6 125.5(2) . . ?
O1 C7 C6 110.8(2) . . ?
O1 C8 H2 109.5 . . ?
O1 C8 H3 109.5 . . ?
H2 C8 H3 109.5 . . ?
O1 C8 H26 109.5 . . ?
H2 C8 H26 109.5 . . ?
H3 C8 H26 109.5 . . ?
C2 C9 H6 109.5 . . ?
C2 C9 H5 109.5 . . ?
H6 C9 H5 109.5 . . ?
C2 C9 H7 109.5 . . ?
H6 C9 H7 109.5 . . ?
H5 C9 H7 109.5 . . ?
N1 C10 C11 103.5(2) . . ?
N1 C10 H12 111.1 . . ?
C11 C10 H12 111.1 . . ?
N1 C10 H11 111.1 . . ?
C11 C10 H11 111.1 . . ?
H12 C10 H11 109.0 . . ?
C12 C11 C10 102.7(2) . . ?
C12 C11 H13 111.2 . . ?
C10 C11 H13 111.2 . . ?
C12 C11 H14 111.2 . . ?
C10 C11 H14 111.2 . . ?
H13 C11 H14 109.1 . . ?
C11 C12 C4 103.4(2) . . ?
C11 C12 H15 111.1 . . ?
C4 C12 H15 111.1 . . ?
C11 C12 H16 111.1 . . ?
C4 C12 H16 111.1 . . ?
H15 C12 H16 109.0 . . ?
C15 C13 C14 111.4(2) . . ?
C15 C13 C6 110.3(2) . . ?
C14 C13 C6 112.0(2) . . ?
C15 C13 H24 107.7 . . ?
C14 C13 H24 107.7 . . ?
C6 C13 H24 107.7 . . ?
C13 C14 H18 109.5 . . ?
C13 C14 H19 109.5 . . ?
H18 C14 H19 109.5 . . ?
C13 C14 H20 109.5 . . ?
H18 C14 H20 109.5 . . ?
H19 C14 H20 109.5 . . ?
C13 C15 H23 109.5 . . ?
C13 C15 H22 109.5 . . ?
H23 C15 H22 109.5 . . ?
C13 C15 H21 109.5 . . ?
H23 C15 H21 109.5 . . ?
H22 C15 H21 109.5 . . ?
C17 C16 H38 109.5 . . ?
C17 C16 H37 109.5 . . ?
H38 C16 H37 109.5 . . ?
C17 C16 H27 109.5 . . ?
H38 C16 H27 109.5 . . ?
H37 C16 H27 109.5 . . ?
C18 C17 C16 110.6(2) . . ?
C18 C17 C27 106.8(2) . . ?
C16 C17 C27 110.7(2) . . ?
C18 C17 H39 109.6 . . ?
C16 C17 H39 109.6 . . ?
C27 C17 H39 109.6 . . ?
O8 C18 N3 120.5(2) . . ?
O8 C18 C17 121.0(2) . . ?
N3 C18 C17 118.4(2) . . ?
N3 C19 C20 112.69(19) . . ?
N3 C19 C26 102.75(19) . . ?
C20 C19 C26 108.24(19) . . ?
N3 C19 H43 111.0 . . ?
C20 C19 H43 111.0 . . ?
C26 C19 H43 111.0 . . ?
O7 C20 N4 123.2(2) . . ?
O7 C20 C19 123.2(2) . . ?
N4 C20 C19 113.48(19) . . ?
N4 C21 C22 109.12(19) . . ?
N4 C21 C28 112.30(18) . . ?
C22 C21 C28 111.75(19) . . ?
N4 C21 H44 107.8 . . ?
C22 C21 H44 107.8 . . ?
C28 C21 H44 107.8 . . ?
O6 C22 O5 123.9(2) . . ?
O6 C22 C21 125.5(2) . . ?
O5 C22 C21 110.6(2) . . ?
O5 C23 H52 109.5 . . ?
O5 C23 H29 109.5 . . ?
H52 C23 H29 109.5 . . ?
O5 C23 H28 109.5 . . ?
H52 C23 H28 109.5 . . ?
H29 C23 H28 109.5 . . ?
N3 C24 C25 103.17(19) . . ?
N3 C24 H31 111.1 . . ?
C25 C24 H31 111.1 . . ?
N3 C24 H32 111.1 . . ?
C25 C24 H32 111.1 . . ?
H31 C24 H32 109.1 . . ?
C26 C25 C24 103.4(2) . . ?
C26 C25 H35 111.1 . . ?
C24 C25 H35 111.1 . . ?
C26 C25 H36 111.1 . . ?
C24 C25 H36 111.1 . . ?
H35 C25 H36 109.0 . . ?
C25 C26 C19 103.3(2) . . ?
C25 C26 H33 111.1 . . ?
C19 C26 H33 111.1 . . ?
C25 C26 H34 111.1 . . ?
C19 C26 H34 111.1 . . ?
H33 C26 H34 109.1 . . ?
C17 C27 H42 109.5 . . ?
C17 C27 H41 109.5 . . ?
H42 C27 H41 109.5 . . ?
C17 C27 H40 109.5 . . ?
H42 C27 H40 109.5 . . ?
H41 C27 H40 109.5 . . ?
C29 C28 C21 112.4(2) . . ?
C29 C28 C30 112.1(2) . . ?
C21 C28 C30 110.5(2) . . ?
C29 C28 H45 107.2 . . ?
C21 C28 H45 107.2 . . ?
C30 C28 H45 107.2 . . ?
C28 C29 H47 109.5 . . ?
C28 C29 H46 109.5 . . ?
H47 C29 H46 109.5 . . ?
C28 C29 H48 109.5 . . ?
H47 C29 H48 109.5 . . ?
H46 C29 H48 109.5 . . ?
C28 C30 H49 109.5 . . ?
C28 C30 H50 109.5 . . ?
H49 C30 H50 109.5 . . ?
C28 C30 H51 109.5 . . ?
H49 C30 H51 109.5 . . ?
H50 C30 H51 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
C4 N1 C3 O4 -179.1(2) . . . . ?
C10 N1 C3 O4 -1.5(3) . . . . ?
C4 N1 C3 C2 -1.7(3) . . . . ?
C10 N1 C3 C2 175.8(2) . . . . ?
C9 C2 C3 O4 -44.2(3) . . . . ?
C1 C2 C3 O4 76.7(3) . . . . ?
C9 C2 C3 N1 138.5(2) . . . . ?
C1 C2 C3 N1 -100.6(2) . . . . ?
C3 N1 C4 C5 -77.5(3) . . . . ?
C10 N1 C4 C5 104.7(2) . . . . ?
C3 N1 C4 C12 166.5(2) . . . . ?
C10 N1 C4 C12 -11.3(3) . . . . ?
C6 N2 C5 O3 -7.6(4) . . . . ?
C6 N2 C5 C4 169.1(2) . . . . ?
N1 C4 C5 O3 -24.8(3) . . . . ?
C12 C4 C5 O3 87.7(3) . . . . ?
N1 C4 C5 N2 158.5(2) . . . . ?
C12 C4 C5 N2 -89.0(2) . . . . ?
C5 N2 C6 C7 -120.0(2) . . . . ?
C5 N2 C6 C13 115.5(3) . . . . ?
C8 O1 C7 O2 -4.6(4) . . . . ?
C8 O1 C7 C6 174.1(2) . . . . ?
N2 C6 C7 O2 -2.0(4) . . . . ?
C13 C6 C7 O2 123.1(3) . . . . ?
N2 C6 C7 O1 179.3(2) . . . . ?
C13 C6 C7 O1 -55.6(3) . . . . ?
C3 N1 C10 C11 168.9(2) . . . . ?
C4 N1 C10 C11 -13.2(3) . . . . ?
N1 C10 C11 C12 32.5(3) . . . . ?
C10 C11 C12 C4 -39.7(3) . . . . ?
N1 C4 C12 C11 31.3(2) . . . . ?
C5 C4 C12 C11 -88.2(2) . . . . ?
N2 C6 C13 C15 -59.7(3) . . . . ?
C7 C6 C13 C15 177.1(2) . . . . ?
N2 C6 C13 C14 64.9(3) . . . . ?
C7 C6 C13 C14 -58.3(3) . . . . ?
C19 N3 C18 O8 178.1(2) . . . . ?
C24 N3 C18 O8 -0.1(3) . . . . ?
C19 N3 C18 C17 -4.9(3) . . . . ?
C24 N3 C18 C17 176.9(2) . . . . ?
C16 C17 C18 O8 -39.0(3) . . . . ?
C27 C17 C18 O8 81.5(3) . . . . ?
C16 C17 C18 N3 144.1(2) . . . . ?
C27 C17 C18 N3 -95.4(2) . . . . ?
C18 N3 C19 C20 -73.2(3) . . . . ?
C24 N3 C19 C20 105.1(2) . . . . ?
C18 N3 C19 C26 170.5(2) . . . . ?
C24 N3 C19 C26 -11.1(2) . . . . ?
C21 N4 C20 O7 -12.4(4) . . . . ?
C21 N4 C20 C19 163.8(2) . . . . ?
N3 C19 C20 O7 -33.1(3) . . . . ?
C26 C19 C20 O7 79.8(3) . . . . ?
N3 C19 C20 N4 150.6(2) . . . . ?
C26 C19 C20 N4 -96.5(2) . . . . ?
C20 N4 C21 C22 -75.1(3) . . . . ?
C20 N4 C21 C28 160.4(2) . . . . ?
C23 O5 C22 O6 -2.0(3) . . . . ?
C23 O5 C22 C21 176.3(2) . . . . ?
N4 C21 C22 O6 4.8(3) . . . . ?
C28 C21 C22 O6 129.6(2) . . . . ?
N4 C21 C22 O5 -173.45(19) . . . . ?
C28 C21 C22 O5 -48.6(3) . . . . ?
C18 N3 C24 C25 165.8(2) . . . . ?
C19 N3 C24 C25 -12.7(3) . . . . ?
N3 C24 C25 C26 31.6(2) . . . . ?
C24 C25 C26 C19 -38.7(2) . . . . ?
N3 C19 C26 C25 30.5(2) . . . . ?
C20 C19 C26 C25 -88.9(2) . . . . ?
N4 C21 C28 C29 66.1(3) . . . . ?
C22 C21 C28 C29 -56.9(3) . . . . ?
N4 C21 C28 C30 -59.9(3) . . . . ?
C22 C21 C28 C30 177.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.043
