# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_nactetramer
_database_code_depnum_ccdc_archive 'CCDC 2049402'
loop_
_audit_author_name
_audit_author_address
'Ryohei Doi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2022-11-18 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C35 H60 N4 O7'
_chemical_formula_moiety         'C35 H60 N4 O7'
_chemical_formula_weight         648.87
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
_space_group_IT_number           1
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.5195(2)
_cell_length_b                   9.5196(2)
_cell_length_c                   11.9808(3)
_cell_angle_alpha                104.374(7)
_cell_angle_beta                 96.543(7)
_cell_angle_gamma                109.840(8)
_cell_volume                     965.61(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    10686
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      68.16
_cell_measurement_temperature    133
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344.00
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_T_max  0.943

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      133
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            11294
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_theta_max         68.162
_diffrn_reflns_theta_min         3.902
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_point_group_measured_fraction_full 0.834
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             5883
_reflns_number_gt                5536
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_max     0.681
_reflns_Friedel_fraction_full    0.685

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0900
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         5883
_refine_ls_number_parameters     439
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0438P)²+0.2138P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.20
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 2058 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(9)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.4280(2) 0.4014(3) -0.03006(17) 0.0342(5) Uani 1 1 d . . . . .
O2 O 0.6460(2) 0.0691(3) 0.18204(17) 0.0319(5) Uani 1 1 d . . . . .
O3 O 0.7822(2) 0.6162(3) 0.54830(19) 0.0409(6) Uani 1 1 d . . . . .
O4 O 0.4841(3) -0.1194(3) 0.5078(2) 0.0422(6) Uani 1 1 d . . . . .
O7 O 0.7200(3) 0.4684(3) 0.3608(2) 0.0564(7) Uani 1 1 d . . . . .
O10 O 0.5747(3) -0.0797(3) -0.25692(18) 0.0462(6) Uani 1 1 d . . . . .
O47 O 0.3203(3) 0.0802(3) -0.46572(19) 0.0449(6) Uani 1 1 d . . . . .
N5 N 0.6749(3) 0.0320(3) 0.3613(2) 0.0268(5) Uani 1 1 d . . . . .
N6 N 0.6116(3) 0.0394(3) -0.0628(2) 0.0272(5) Uani 1 1 d . . . . .
N9 N 0.4811(3) 0.3829(3) 0.1530(2) 0.0277(5) Uani 1 1 d . . . . .
N11 N 0.3315(3) 0.2050(4) -0.2765(2) 0.0347(6) Uani 1 1 d . . . . .
C12 C 0.5270(3) -0.0672(4) -0.1641(2) 0.0298(7) Uani 1 1 d . . . . .
C13 C 0.8013(3) 0.3020(4) 0.0352(2) 0.0288(6) Uani 1 1 d . . . . .
H13 H 0.7951 0.3031 0.1182 0.035 Uiso 1 1 calc R U . . .
C14 C 0.9693(3) 0.5317(4) 0.4746(2) 0.0296(6) Uani 1 1 d . . . . .
H14 H 1.0075 0.5563 0.5612 0.035 Uiso 1 1 calc R U . . .
C15 C 0.5212(3) 0.4321(3) 0.0619(2) 0.0273(6) Uani 1 1 d . . . . .
C16 C 0.3234(3) 0.2917(3) 0.1561(2) 0.0254(6) Uani 1 1 d . . . . .
H16 H 0.2695 0.2230 0.0738 0.030 Uiso 1 1 calc R U . . .
C17 C 0.9685(3) 0.3724(4) 0.4113(2) 0.0275(6) Uani 1 1 d . . . . .
H17 H 0.9404 0.3407 0.3231 0.033 Uiso 1 1 calc R U . . .
C18 C 0.8410(3) 0.0748(3) 0.3821(2) 0.0272(6) Uani 1 1 d . . . . .
H18 H 0.8718 0.0688 0.3046 0.033 Uiso 1 1 calc R U . . .
C19 C 0.7703(3) 0.1445(4) -0.0499(3) 0.0297(7) Uani 1 1 d . . . . .
H19 H 0.7840 0.1584 -0.1286 0.036 Uiso 1 1 calc R U . . .
C20 C 0.5909(3) 0.0295(3) 0.2635(2) 0.0224(6) Uani 1 1 d . . . . .
C21 C 0.4192(3) -0.0337(3) 0.2555(2) 0.0252(6) Uani 1 1 d . . . . .
H21 H 0.4008 -0.0045 0.3371 0.030 Uiso 1 1 calc R U . . .
C22 C 0.9252(3) 0.2399(4) 0.4631(2) 0.0268(6) Uani 1 1 d . . . . .
H22 H 0.8982 0.2635 0.5420 0.032 Uiso 1 1 calc R U . . .
C23 C 0.3373(3) 0.0333(3) 0.1808(2) 0.0254(6) Uani 1 1 d . . . . .
H23 H 0.3440 0.0074 0.0959 0.030 Uiso 1 1 calc R U . . .
C24 C 0.2389(3) 0.3982(4) 0.1961(3) 0.0329(7) Uani 1 1 d . . . . .
H24A H 0.1341 0.3345 0.1973 0.039 Uiso 1 1 calc R U . . .
H24B H 0.2918 0.4701 0.2754 0.039 Uiso 1 1 calc R U . . .
H24C H 0.2361 0.4589 0.1412 0.039 Uiso 1 1 calc R U . . .
C25 C 0.8098(3) 0.5322(4) 0.4534(3) 0.0304(7) Uani 1 1 d . . . . .
C26 C 0.7531(3) 0.4193(4) -0.0051(3) 0.0308(7) Uani 1 1 d . . . . .
H26 H 0.7053 0.3855 -0.0910 0.037 Uiso 1 1 calc R U . . .
C27 C 0.2117(3) 0.0031(4) -0.1890(2) 0.0325(7) Uani 1 1 d . . . . .
H27 H 0.2633 0.0668 -0.1052 0.039 Uiso 1 1 calc R U . . .
C28 C 0.3669(3) -0.1725(4) -0.1628(3) 0.0327(7) Uani 1 1 d . . . . .
H28 H 0.3533 -0.1489 -0.0796 0.039 Uiso 1 1 calc R U . . .
C29 C 0.3229(3) 0.1869(3) 0.2312(2) 0.0251(6) Uani 1 1 d . . . . .
H29 H 0.3712 0.2416 0.3169 0.030 Uiso 1 1 calc R U . . .
C30 C 0.6916(3) 0.5227(4) 0.0748(3) 0.0323(7) Uani 1 1 d . . . . .
H30 H 0.7448 0.5472 0.1583 0.039 Uiso 1 1 calc R U . . .
C31 C 1.0896(3) 0.3228(4) 0.4606(3) 0.0323(7) Uani 1 1 d . . . . .
H31A H 1.1609 0.3930 0.5363 0.039 Uiso 1 1 calc R U . . .
H31B H 1.1351 0.2662 0.4042 0.039 Uiso 1 1 calc R U . . .
C32 C 0.1860(3) 0.0366(4) 0.2038(3) 0.0328(7) Uani 1 1 d . . . . .
H32A H 0.1035 0.0105 0.1348 0.039 Uiso 1 1 calc R U . . .
H32B H 0.1511 0.0027 0.2710 0.039 Uiso 1 1 calc R U . . .
C33 C 0.3916(4) 0.1845(4) -0.3719(3) 0.0390(8) Uani 1 1 d . . . . .
C34 C 0.8790(3) 0.0703(4) -0.0121(3) 0.0356(7) Uani 1 1 d . . . . .
H34A H 0.9848 0.1408 -0.0036 0.043 Uiso 1 1 calc R U . . .
H34B H 0.8646 0.0522 0.0636 0.043 Uiso 1 1 calc R U . . .
H34C H 0.8573 -0.0300 -0.0720 0.043 Uiso 1 1 calc R U . . .
C35 C 0.3576(4) -0.2117(4) 0.2069(3) 0.0369(7) Uani 1 1 d . . . . .
H35A H 0.4123 -0.2525 0.2567 0.044 Uiso 1 1 calc R U . . .
H35B H 0.2482 -0.2548 0.2065 0.044 Uiso 1 1 calc R U . . .
H35C H 0.3725 -0.2426 0.1262 0.044 Uiso 1 1 calc R U . . .
C36 C 0.1855(4) 0.0959(4) -0.2689(3) 0.0347(7) Uani 1 1 d . . . . .
H36 H 0.1341 0.0205 -0.3497 0.042 Uiso 1 1 calc R U . . .
C37 C 0.2513(3) -0.1365(4) -0.2358(3) 0.0324(7) Uani 1 1 d . . . . .
H37 H 0.2494 -0.1651 -0.3223 0.039 Uiso 1 1 calc R U . . .
C38 C 1.0751(4) 0.6591(4) 0.4312(3) 0.0399(8) Uani 1 1 d . . . . .
H38A H 1.1788 0.6596 0.4446 0.048 Uiso 1 1 calc R U . . .
H38B H 1.0370 0.6372 0.3467 0.048 Uiso 1 1 calc R U . . .
H38C H 1.0769 0.7617 0.4747 0.048 Uiso 1 1 calc R U . . .
C39 C 0.6357(4) 0.6338(5) 0.5326(4) 0.0517(10) Uani 1 1 d . . . . .
H39A H 0.6267 0.6974 0.6074 0.062 Uiso 1 1 calc R U . . .
H39B H 0.6295 0.6858 0.4722 0.062 Uiso 1 1 calc R U . . .
H39C H 0.5525 0.5301 0.5077 0.062 Uiso 1 1 calc R U . . .
C40 C 0.0973(4) -0.1581(4) -0.2054(3) 0.0404(8) Uani 1 1 d . . . . .
H40A H 0.0067 -0.2019 -0.2714 0.048 Uiso 1 1 calc R U . . .
H40B H 0.0786 -0.1893 -0.1339 0.048 Uiso 1 1 calc R U . . .
C41 C 0.8817(4) -0.0434(4) 0.4308(3) 0.0376(7) Uani 1 1 d . . . . .
H41A H 0.9927 -0.0148 0.4448 0.045 Uiso 1 1 calc R U . . .
H41B H 0.8483 -0.0428 0.5053 0.045 Uiso 1 1 calc R U . . .
H41C H 0.8303 -0.1485 0.3737 0.045 Uiso 1 1 calc R U . . .
C42 C 0.9203(4) 0.4471(4) 0.0226(3) 0.0405(8) Uani 1 1 d . . . . .
H42A H 0.9853 0.5308 0.0957 0.049 Uiso 1 1 calc R U . . .
H42B H 0.9716 0.4335 -0.0444 0.049 Uiso 1 1 calc R U . . .
C43 C 0.7187(4) 0.6769(4) 0.0473(3) 0.0462(9) Uani 1 1 d . . . . .
H43A H 0.6773 0.7404 0.1009 0.055 Uiso 1 1 calc R U . . .
H43B H 0.8288 0.7345 0.0578 0.055 Uiso 1 1 calc R U . . .
H43C H 0.6675 0.6547 -0.0344 0.055 Uiso 1 1 calc R U . . .
C44 C 0.0833(4) 0.1835(5) -0.2306(3) 0.0460(9) Uani 1 1 d . . . . .
H44A H -0.0147 0.1091 -0.2257 0.055 Uiso 1 1 calc R U . . .
H44B H 0.1334 0.2619 -0.1530 0.055 Uiso 1 1 calc R U . . .
H44C H 0.0654 0.2362 -0.2883 0.055 Uiso 1 1 calc R U . . .
C45 C 0.3437(4) -0.3452(4) -0.2081(3) 0.0515(10) Uani 1 1 d . . . . .
H45A H 0.4201 -0.3651 -0.1592 0.062 Uiso 1 1 calc R U . . .
H45B H 0.2409 -0.4107 -0.2042 0.062 Uiso 1 1 calc R U . . .
H45C H 0.3552 -0.3705 -0.2901 0.062 Uiso 1 1 calc R U . . .
C46 C 0.5542(5) 0.2939(5) -0.3564(4) 0.0605(11) Uani 1 1 d . . . . .
H46A H 0.5900 0.3677 -0.2762 0.073 Uiso 1 1 calc R U . . .
H46B H 0.6191 0.2331 -0.3691 0.073 Uiso 1 1 calc R U . . .
H46C H 0.5595 0.3522 -0.4137 0.073 Uiso 1 1 calc R U . . .
H8 H 0.519(4) -0.097(4) 0.582(4) 0.052(11) Uiso 1 1 d . . . . .
H48 H 0.421(5) -0.068(5) 0.513(4) 0.065(13) Uiso 1 1 d . . . . .
H49 H 0.632(4) 0.002(4) 0.415(3) 0.037(9) Uiso 1 1 d . . . . .
H50 H 0.544(4) 0.406(4) 0.211(3) 0.025(8) Uiso 1 1 d . . . . .
H51 H 0.582(4) 0.042(4) 0.001(3) 0.042(10) Uiso 1 1 d . . . . .
H52 H 0.390(4) 0.281(4) -0.215(3) 0.035(9) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2014/8 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C15 1.236(3) . ?
O2 C20 1.239(3) . ?
O3 C25 1.327(3) . ?
O3 C39 1.457(4) . ?
O4 H8 0.86(4) . ?
O4 H48 0.89(5) . ?
O7 C25 1.195(3) . ?
O10 C12 1.242(3) . ?
O47 C33 1.235(4) . ?
N5 C20 1.331(3) . ?
N5 C18 1.466(3) . ?
N5 H49 0.86(3) . ?
N6 C12 1.328(4) . ?
N6 C19 1.467(4) . ?
N6 H51 0.84(4) . ?
N9 C15 1.336(4) . ?
N9 C16 1.467(3) . ?
N9 H50 0.79(3) . ?
N11 C33 1.336(4) . ?
N11 C36 1.455(4) . ?
N11 H52 0.87(3) . ?
C12 C28 1.518(4) . ?
C13 C19 1.499(4) . ?
C13 C26 1.501(4) . ?
C13 C42 1.515(4) . ?
C13 H13 1.0000 . ?
C14 C25 1.512(4) . ?
C14 C17 1.515(4) . ?
C14 C38 1.535(4) . ?
C14 H14 1.0000 . ?
C15 C30 1.525(4) . ?
C16 C29 1.500(4) . ?
C16 C24 1.519(4) . ?
C16 H16 1.0000 . ?
C17 C22 1.497(4) . ?
C17 C31 1.502(4) . ?
C17 H17 1.0000 . ?
C18 C22 1.505(4) . ?
C18 C41 1.525(4) . ?
C18 H18 1.0000 . ?
C19 C34 1.524(4) . ?
C19 H19 1.0000 . ?
C20 C21 1.520(4) . ?
C21 C23 1.509(4) . ?
C21 C35 1.521(4) . ?
C21 H21 1.0000 . ?
C22 C31 1.502(4) . ?
C22 H22 1.0000 . ?
C23 C29 1.496(4) . ?
C23 C32 1.506(4) . ?
C23 H23 1.0000 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C26 C42 1.504(4) . ?
C26 C30 1.509(4) . ?
C26 H26 1.0000 . ?
C27 C37 1.498(4) . ?
C27 C40 1.499(5) . ?
C27 C36 1.509(4) . ?
C27 H27 1.0000 . ?
C28 C37 1.510(4) . ?
C28 C45 1.525(5) . ?
C28 H28 1.0000 . ?
C29 C32 1.502(4) . ?
C29 H29 1.0000 . ?
C30 C43 1.528(4) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C46 1.503(5) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 C44 1.522(4) . ?
C36 H36 1.0000 . ?
C37 C40 1.509(4) . ?
C37 H37 1.0000 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 O3 C39 115.9(2) . . ?
H8 O4 H48 98(4) . . ?
C20 N5 C18 124.0(2) . . ?
C20 N5 H49 120(2) . . ?
C18 N5 H49 116(2) . . ?
C12 N6 C19 123.1(2) . . ?
C12 N6 H51 121(2) . . ?
C19 N6 H51 115(2) . . ?
C15 N9 C16 124.0(2) . . ?
C15 N9 H50 120(2) . . ?
C16 N9 H50 116(2) . . ?
C33 N11 C36 123.2(3) . . ?
C33 N11 H52 116(2) . . ?
C36 N11 H52 120(2) . . ?
O10 C12 N6 122.0(3) . . ?
O10 C12 C28 120.9(3) . . ?
N6 C12 C28 117.2(2) . . ?
C19 C13 C26 120.3(2) . . ?
C19 C13 C42 119.4(3) . . ?
C26 C13 C42 59.83(19) . . ?
C19 C13 H13 115.4 . . ?
C26 C13 H13 115.4 . . ?
C42 C13 H13 115.4 . . ?
C25 C14 C17 110.7(2) . . ?
C25 C14 C38 108.9(3) . . ?
C17 C14 C38 110.4(2) . . ?
C25 C14 H14 108.9 . . ?
C17 C14 H14 108.9 . . ?
C38 C14 H14 108.9 . . ?
O1 C15 N9 122.7(3) . . ?
O1 C15 C30 121.2(3) . . ?
N9 C15 C30 116.0(2) . . ?
N9 C16 C29 110.0(2) . . ?
N9 C16 C24 111.2(2) . . ?
C29 C16 C24 112.5(2) . . ?
N9 C16 H16 107.6 . . ?
C29 C16 H16 107.6 . . ?
C24 C16 H16 107.6 . . ?
C22 C17 C31 60.13(19) . . ?
C22 C17 C14 121.7(2) . . ?
C31 C17 C14 118.5(2) . . ?
C22 C17 H17 115.2 . . ?
C31 C17 H17 115.2 . . ?
C14 C17 H17 115.2 . . ?
N5 C18 C22 111.4(2) . . ?
N5 C18 C41 109.5(2) . . ?
C22 C18 C41 111.6(2) . . ?
N5 C18 H18 108.1 . . ?
C22 C18 H18 108.1 . . ?
C41 C18 H18 108.1 . . ?
N6 C19 C13 109.7(2) . . ?
N6 C19 C34 109.7(2) . . ?
C13 C19 C34 112.5(2) . . ?
N6 C19 H19 108.3 . . ?
C13 C19 H19 108.3 . . ?
C34 C19 H19 108.3 . . ?
O2 C20 N5 123.3(3) . . ?
O2 C20 C21 121.6(2) . . ?
N5 C20 C21 115.0(2) . . ?
C23 C21 C20 112.5(2) . . ?
C23 C21 C35 110.9(2) . . ?
C20 C21 C35 108.4(2) . . ?
C23 C21 H21 108.3 . . ?
C20 C21 H21 108.3 . . ?
C35 C21 H21 108.3 . . ?
C17 C22 C31 60.09(19) . . ?
C17 C22 C18 119.2(2) . . ?
C31 C22 C18 118.2(2) . . ?
C17 C22 H22 116.0 . . ?
C31 C22 H22 116.0 . . ?
C18 C22 H22 116.0 . . ?
C29 C23 C32 60.05(19) . . ?
C29 C23 C21 121.6(2) . . ?
C32 C23 C21 117.7(2) . . ?
C29 C23 H23 115.4 . . ?
C32 C23 H23 115.4 . . ?
C21 C23 H23 115.4 . . ?
C16 C24 H24A 109.5 . . ?
C16 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C16 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O7 C25 O3 123.5(3) . . ?
O7 C25 C14 124.1(3) . . ?
O3 C25 C14 112.4(2) . . ?
C13 C26 C42 60.52(19) . . ?
C13 C26 C30 120.5(2) . . ?
C42 C26 C30 119.8(3) . . ?
C13 C26 H26 115.1 . . ?
C42 C26 H26 115.1 . . ?
C30 C26 H26 115.1 . . ?
C37 C27 C40 60.5(2) . . ?
C37 C27 C36 119.8(2) . . ?
C40 C27 C36 120.4(3) . . ?
C37 C27 H27 115.1 . . ?
C40 C27 H27 115.1 . . ?
C36 C27 H27 115.1 . . ?
C37 C28 C12 109.2(3) . . ?
C37 C28 C45 111.2(3) . . ?
C12 C28 C45 110.9(3) . . ?
C37 C28 H28 108.5 . . ?
C12 C28 H28 108.5 . . ?
C45 C28 H28 108.5 . . ?
C23 C29 C16 120.0(2) . . ?
C23 C29 C32 60.32(19) . . ?
C16 C29 C32 118.3(2) . . ?
C23 C29 H29 115.7 . . ?
C16 C29 H29 115.7 . . ?
C32 C29 H29 115.7 . . ?
C26 C30 C15 108.5(2) . . ?
C26 C30 C43 112.0(3) . . ?
C15 C30 C43 110.6(2) . . ?
C26 C30 H30 108.5 . . ?
C15 C30 H30 108.5 . . ?
C43 C30 H30 108.5 . . ?
C17 C31 C22 59.77(19) . . ?
C17 C31 H31A 117.8 . . ?
C22 C31 H31A 117.8 . . ?
C17 C31 H31B 117.8 . . ?
C22 C31 H31B 117.8 . . ?
H31A C31 H31B 114.9 . . ?
C29 C32 C23 59.63(18) . . ?
C29 C32 H32A 117.8 . . ?
C23 C32 H32A 117.8 . . ?
C29 C32 H32B 117.8 . . ?
C23 C32 H32B 117.8 . . ?
H32A C32 H32B 114.9 . . ?
O47 C33 N11 122.5(3) . . ?
O47 C33 C46 122.0(3) . . ?
N11 C33 C46 115.5(3) . . ?
C19 C34 H34A 109.5 . . ?
C19 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C19 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C21 C35 H35A 109.5 . . ?
C21 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C21 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
N11 C36 C27 109.8(2) . . ?
N11 C36 C44 110.1(3) . . ?
C27 C36 C44 113.2(2) . . ?
N11 C36 H36 107.8 . . ?
C27 C36 H36 107.8 . . ?
C44 C36 H36 107.8 . . ?
C27 C37 C40 59.8(2) . . ?
C27 C37 C28 121.9(3) . . ?
C40 C37 C28 120.0(3) . . ?
C27 C37 H37 114.7 . . ?
C40 C37 H37 114.7 . . ?
C28 C37 H37 114.7 . . ?
C14 C38 H38A 109.5 . . ?
C14 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C14 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O3 C39 H39A 109.5 . . ?
O3 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O3 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C27 C40 C37 59.7(2) . . ?
C27 C40 H40A 117.8 . . ?
C37 C40 H40A 117.8 . . ?
C27 C40 H40B 117.8 . . ?
C37 C40 H40B 117.8 . . ?
H40A C40 H40B 114.9 . . ?
C18 C41 H41A 109.5 . . ?
C18 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C18 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C26 C42 C13 59.65(19) . . ?
C26 C42 H42A 117.8 . . ?
C13 C42 H42A 117.8 . . ?
C26 C42 H42B 117.8 . . ?
C13 C42 H42B 117.8 . . ?
H42A C42 H42B 114.9 . . ?
C30 C43 H43A 109.5 . . ?
C30 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C30 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C36 C44 H44A 109.5 . . ?
C36 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C36 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C28 C45 H45A 109.5 . . ?
C28 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C28 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C33 C46 H46A 109.5 . . ?
C33 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C33 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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
C19 N6 C12 O10 -3.7(4) . . . . ?
C19 N6 C12 C28 177.4(2) . . . . ?
C16 N9 C15 O1 -1.8(4) . . . . ?
C16 N9 C15 C30 -178.9(2) . . . . ?
C15 N9 C16 C29 150.1(3) . . . . ?
C15 N9 C16 C24 -84.5(3) . . . . ?
C25 C14 C17 C22 -82.1(3) . . . . ?
C38 C14 C17 C22 157.3(3) . . . . ?
C25 C14 C17 C31 -152.7(3) . . . . ?
C38 C14 C17 C31 86.6(3) . . . . ?
C20 N5 C18 C22 101.8(3) . . . . ?
C20 N5 C18 C41 -134.3(3) . . . . ?
C12 N6 C19 C13 144.3(3) . . . . ?
C12 N6 C19 C34 -91.6(3) . . . . ?
C26 C13 C19 N6 -81.2(3) . . . . ?
C42 C13 C19 N6 -151.4(2) . . . . ?
C26 C13 C19 C34 156.4(3) . . . . ?
C42 C13 C19 C34 86.2(3) . . . . ?
C18 N5 C20 O2 -2.9(4) . . . . ?
C18 N5 C20 C21 174.3(2) . . . . ?
O2 C20 C21 C23 -30.2(4) . . . . ?
N5 C20 C21 C23 152.6(2) . . . . ?
O2 C20 C21 C35 92.9(3) . . . . ?
N5 C20 C21 C35 -84.4(3) . . . . ?
C14 C17 C22 C31 -107.0(3) . . . . ?
C31 C17 C22 C18 -107.7(3) . . . . ?
C14 C17 C22 C18 145.4(3) . . . . ?
N5 C18 C22 C17 -89.1(3) . . . . ?
C41 C18 C22 C17 148.2(3) . . . . ?
N5 C18 C22 C31 -158.7(2) . . . . ?
C41 C18 C22 C31 78.6(3) . . . . ?
C20 C21 C23 C29 -85.2(3) . . . . ?
C35 C21 C23 C29 153.1(3) . . . . ?
C20 C21 C23 C32 -155.4(2) . . . . ?
C35 C21 C23 C32 82.9(3) . . . . ?
C39 O3 C25 O7 -2.8(5) . . . . ?
C39 O3 C25 C14 175.0(3) . . . . ?
C17 C14 C25 O7 -39.7(4) . . . . ?
C38 C14 C25 O7 81.9(4) . . . . ?
C17 C14 C25 O3 142.5(3) . . . . ?
C38 C14 C25 O3 -95.9(3) . . . . ?
C19 C13 C26 C42 -108.6(3) . . . . ?
C19 C13 C26 C30 142.2(3) . . . . ?
C42 C13 C26 C30 -109.2(3) . . . . ?
O10 C12 C28 C37 -65.7(4) . . . . ?
N6 C12 C28 C37 113.2(3) . . . . ?
O10 C12 C28 C45 57.3(4) . . . . ?
N6 C12 C28 C45 -123.8(3) . . . . ?
C32 C23 C29 C16 -107.5(3) . . . . ?
C21 C23 C29 C16 146.6(3) . . . . ?
C21 C23 C29 C32 -106.0(3) . . . . ?
N9 C16 C29 C23 -81.6(3) . . . . ?
C24 C16 C29 C23 153.8(3) . . . . ?
N9 C16 C29 C32 -151.8(2) . . . . ?
C24 C16 C29 C32 83.6(3) . . . . ?
C13 C26 C30 C15 -84.2(3) . . . . ?
C42 C26 C30 C15 -155.4(3) . . . . ?
C13 C26 C30 C43 153.4(3) . . . . ?
C42 C26 C30 C43 82.1(3) . . . . ?
O1 C15 C30 C26 -69.5(3) . . . . ?
N9 C15 C30 C26 107.6(3) . . . . ?
O1 C15 C30 C43 53.8(4) . . . . ?
N9 C15 C30 C43 -129.1(3) . . . . ?
C14 C17 C31 C22 112.1(3) . . . . ?
C18 C22 C31 C17 109.2(3) . . . . ?
C16 C29 C32 C23 110.3(3) . . . . ?
C21 C23 C32 C29 112.4(3) . . . . ?
C36 N11 C33 O47 8.0(5) . . . . ?
C36 N11 C33 C46 -170.1(3) . . . . ?
C33 N11 C36 C27 106.5(3) . . . . ?
C33 N11 C36 C44 -128.1(3) . . . . ?
C37 C27 C36 N11 -81.4(3) . . . . ?
C40 C27 C36 N11 -152.6(3) . . . . ?
C37 C27 C36 C44 155.0(3) . . . . ?
C40 C27 C36 C44 83.8(4) . . . . ?
C36 C27 C37 C40 -110.3(3) . . . . ?
C40 C27 C37 C28 -108.7(3) . . . . ?
C36 C27 C37 C28 141.0(3) . . . . ?
C12 C28 C37 C27 -78.9(3) . . . . ?
C45 C28 C37 C27 158.3(3) . . . . ?
C12 C28 C37 C40 -150.0(3) . . . . ?
C45 C28 C37 C40 87.3(4) . . . . ?
C36 C27 C40 C37 109.3(3) . . . . ?
C28 C37 C40 C27 111.7(3) . . . . ?
C30 C26 C42 C13 110.4(3) . . . . ?
C19 C13 C42 C26 110.0(3) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O4 H8 O10 . . 1_556 2.743(3) 0.86(4) 1.89(4) 171(4) no
O4 H48 O47 . . 1_556 2.822(5) 0.89(6) 1.94(5) 169(3) no
N5 H49 O4 . . . 2.944(4) 0.86(4) 2.11(4) 165(2) no
N6 H51 O2 . . . 2.846(3) 0.84(4) 2.11(4) 146(4) no
N9 H50 O7 . . . 2.912(3) 0.79(3) 2.12(3) 178(4) no
N11 H52 O1 . . . 2.921(3) 0.87(3) 2.15(3) 149(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_nboctetramer
_database_code_depnum_ccdc_archive 'CCDC 2049403'
loop_
_audit_author_name
_audit_author_address
'Ryohei Doi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2022-11-18 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C38 H66 N4 O8'
_chemical_formula_moiety         'C38 H66 N4 O8'
_chemical_formula_weight         706.96
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.77455(19)
_cell_length_b                   17.1488(3)
_cell_length_c                   24.9042(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     4174.50(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    35196
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      68.16
_cell_measurement_temperature    133
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.330
_exptl_crystal_size_min          0.270
_exptl_crystal_density_diffrn    1.125
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1544.00
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_T_max  0.843

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      133
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            45486
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_theta_max         68.208
_diffrn_reflns_theta_min         3.129
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             7598
_reflns_number_gt                6343
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.776
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.991

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1172
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         7598
_refine_ls_number_parameters     479
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0631P)²+0.7252P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 2260 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(4)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.8338(2) 0.12097(15) 0.25503(8) 0.0480(6) Uani 1 1 d . . . . .
O2 O 0.8172(3) 0.1476(2) 0.16881(10) 0.0819(10) Uani 1 1 d . . . . .
O3 O 0.9086(2) -0.11588(16) 0.08771(9) 0.0555(7) Uani 1 1 d . . . . .
O4 O 0.6646(3) 0.10895(16) -0.01481(8) 0.0543(7) Uani 1 1 d . . . . .
O5 O 0.9345(3) -0.10281(16) -0.11639(9) 0.0568(7) Uani 1 1 d . . . . .
O6 O 0.8586(2) 0.13368(14) -0.15012(8) 0.0420(5) Uani 1 1 d . . . . .
O7 O 0.7223(2) 0.07914(14) -0.21474(8) 0.0464(6) Uani 1 1 d . . . . .
O8 O 1.3316(9) 0.1039(7) 0.3226(5) 0.351(7) Uani 1 1 d . . . . .
N1 N 0.9074(3) -0.09957(17) 0.17777(12) 0.0470(7) Uani 1 1 d . . . . .
N2 N 0.6745(3) 0.08988(18) 0.07405(11) 0.0451(7) Uani 1 1 d . . . . .
N3 N 0.9275(3) -0.07958(16) -0.02721(11) 0.0409(6) Uani 1 1 d . . . . .
N4 N 0.6702(3) 0.07372(17) -0.12570(10) 0.0407(6) Uani 1 1 d . . . . .
C1 C 0.6871(4) 0.1114(3) 0.25711(14) 0.0562(10) Uani 1 1 d . . . . .
H1A H 0.6603 0.0668 0.2349 0.067 Uiso 1 1 calc R U . . .
H1B H 0.6427 0.1587 0.2435 0.067 Uiso 1 1 calc R U . . .
H1C H 0.6587 0.1024 0.2943 0.067 Uiso 1 1 calc R U . . .
C2 C 0.8866(4) 0.1362(2) 0.20785(12) 0.0461(8) Uani 1 1 d . . . . .
C3 C 1.0403(4) 0.1377(2) 0.20752(14) 0.0526(9) Uani 1 1 d . . . . .
H3 H 1.0742 0.1409 0.2453 0.063 Uiso 1 1 calc R U . . .
C4 C 1.0927(5) 0.2087(2) 0.17603(18) 0.0681(12) Uani 1 1 d . . . . .
H4A H 1.0527 0.2086 0.1399 0.082 Uiso 1 1 calc R U . . .
H4B H 1.1926 0.2062 0.1733 0.082 Uiso 1 1 calc R U . . .
H4C H 1.0662 0.2566 0.1948 0.082 Uiso 1 1 calc R U . . .
C5 C 1.0909(4) 0.0623(2) 0.18245(13) 0.0446(8) Uani 1 1 d . . . . .
H5 H 1.0769 0.0580 0.1428 0.054 Uiso 1 1 calc R U . . .
C6 C 1.2208(4) 0.0257(2) 0.20334(15) 0.0530(9) Uani 1 1 d . . . . .
H6A H 1.2839 0.0020 0.1769 0.064 Uiso 1 1 calc R U . . .
H6B H 1.2661 0.0508 0.2344 0.064 Uiso 1 1 calc R U . . .
C7 C 1.0854(4) -0.0138(2) 0.21281(13) 0.0471(8) Uani 1 1 d . . . . .
H7 H 1.0493 -0.0105 0.2503 0.057 Uiso 1 1 calc R U . . .
C8 C 1.0544(4) -0.0882(2) 0.18352(13) 0.0462(8) Uani 1 1 d . . . . .
H8 H 1.0948 -0.0843 0.1467 0.055 Uiso 1 1 calc R U . . .
C9 C 1.1180(4) -0.1582(2) 0.21130(16) 0.0613(10) Uani 1 1 d . . . . .
H9A H 1.0958 -0.2057 0.1912 0.074 Uiso 1 1 calc R U . . .
H9B H 1.0816 -0.1624 0.2479 0.074 Uiso 1 1 calc R U . . .
H9C H 1.2175 -0.1517 0.2128 0.074 Uiso 1 1 calc R U . . .
C10 C 0.8475(3) -0.1163(2) 0.13073(13) 0.0437(8) Uani 1 1 d . . . . .
C11 C 0.6973(4) -0.1399(2) 0.13364(16) 0.0512(9) Uani 1 1 d . . . . .
H11 H 0.6643 -0.1321 0.1713 0.061 Uiso 1 1 calc R U . . .
C12 C 0.6873(5) -0.2272(3) 0.1197(3) 0.0977(18) Uani 1 1 d . . . . .
H12A H 0.7077 -0.2347 0.0816 0.117 Uiso 1 1 calc R U . . .
H12B H 0.5946 -0.2459 0.1274 0.117 Uiso 1 1 calc R U . . .
H12C H 0.7533 -0.2565 0.1414 0.117 Uiso 1 1 calc R U . . .
C13 C 0.6109(4) -0.0909(2) 0.09658(14) 0.0480(9) Uani 1 1 d . . . . .
H13 H 0.6375 -0.0922 0.0578 0.058 Uiso 1 1 calc R U . . .
C14 C 0.4595(4) -0.0852(2) 0.10774(15) 0.0502(9) Uani 1 1 d . . . . .
H14A H 0.3965 -0.0844 0.0766 0.060 Uiso 1 1 calc R U . . .
H14B H 0.4236 -0.1119 0.1400 0.060 Uiso 1 1 calc R U . . .
C15 C 0.5510(3) -0.01601(18) 0.11596(12) 0.0391(7) Uani 1 1 d . . . . .
H15 H 0.5711 -0.0031 0.1543 0.047 Uiso 1 1 calc R U . . .
C16 C 0.5402(4) 0.0531(2) 0.07901(13) 0.0455(8) Uani 1 1 d . . . . .
H16 H 0.5130 0.0335 0.0427 0.055 Uiso 1 1 calc R U . . .
C17 C 0.4322(4) 0.1108(3) 0.09744(18) 0.0702(12) Uani 1 1 d . . . . .
H17A H 0.4290 0.1549 0.0724 0.084 Uiso 1 1 calc R U . . .
H17B H 0.4552 0.1298 0.1335 0.084 Uiso 1 1 calc R U . . .
H17C H 0.3427 0.0851 0.0983 0.084 Uiso 1 1 calc R U . . .
C18 C 0.7271(3) 0.11472(17) 0.02799(12) 0.0359(7) Uani 1 1 d . . . . .
C19 C 0.8685(3) 0.15048(18) 0.03069(13) 0.0399(7) Uani 1 1 d . . . . .
H19 H 0.9032 0.1457 0.0683 0.048 Uiso 1 1 calc R U . . .
C20 C 0.8599(5) 0.2372(2) 0.01621(17) 0.0628(11) Uani 1 1 d . . . . .
H20A H 0.8202 0.2429 -0.0197 0.075 Uiso 1 1 calc R U . . .
H20B H 0.9518 0.2600 0.0166 0.075 Uiso 1 1 calc R U . . .
H20C H 0.8021 0.2642 0.0424 0.075 Uiso 1 1 calc R U . . .
C21 C 0.9639(3) 0.10674(19) -0.00613(12) 0.0394(7) Uani 1 1 d . . . . .
H21 H 0.9394 0.1080 -0.0451 0.047 Uiso 1 1 calc R U . . .
C22 C 1.1145(4) 0.1066(2) 0.00608(14) 0.0491(9) Uani 1 1 d . . . . .
H22A H 1.1788 0.1092 -0.0246 0.059 Uiso 1 1 calc R U . . .
H22B H 1.1455 0.1339 0.0389 0.059 Uiso 1 1 calc R U . . .
C23 C 1.0322(3) 0.03366(19) 0.01287(12) 0.0403(7) Uani 1 1 d . . . . .
H23 H 1.0122 0.0186 0.0509 0.048 Uiso 1 1 calc R U . . .
C24 C 1.0533(3) -0.03342(19) -0.02552(13) 0.0431(8) Uani 1 1 d . . . . .
H24 H 1.0697 -0.0114 -0.0622 0.052 Uiso 1 1 calc R U . . .
C25 C 1.1752(4) -0.0835(2) -0.01052(17) 0.0620(10) Uani 1 1 d . . . . .
H25A H 1.1846 -0.1261 -0.0365 0.074 Uiso 1 1 calc R U . . .
H25B H 1.1615 -0.1053 0.0255 0.074 Uiso 1 1 calc R U . . .
H25C H 1.2584 -0.0516 -0.0108 0.074 Uiso 1 1 calc R U . . .
C26 C 0.8778(3) -0.10995(19) -0.07264(12) 0.0391(7) Uani 1 1 d . . . . .
C27 C 0.7427(3) -0.15323(19) -0.06825(12) 0.0410(8) Uani 1 1 d . . . . .
H27 H 0.7079 -0.1488 -0.0306 0.049 Uiso 1 1 calc R U . . .
C28 C 0.7628(5) -0.2395(2) -0.08204(16) 0.0598(10) Uani 1 1 d . . . . .
H28A H 0.8013 -0.2442 -0.1182 0.072 Uiso 1 1 calc R U . . .
H28B H 0.6744 -0.2664 -0.0806 0.072 Uiso 1 1 calc R U . . .
H28C H 0.8256 -0.2633 -0.0561 0.072 Uiso 1 1 calc R U . . .
C29 C 0.6417(3) -0.11516(19) -0.10586(12) 0.0387(7) Uani 1 1 d . . . . .
H29 H 0.6689 -0.1167 -0.1446 0.046 Uiso 1 1 calc R U . . .
C30 C 0.4900(4) -0.1183(2) -0.09636(15) 0.0495(9) Uani 1 1 d . . . . .
H30A H 0.4572 -0.1450 -0.0636 0.059 Uiso 1 1 calc R U . . .
H30B H 0.4297 -0.1237 -0.1281 0.059 Uiso 1 1 calc R U . . .
C31 C 0.5664(3) -0.04237(18) -0.08950(12) 0.0387(7) Uani 1 1 d . . . . .
H31 H 0.5809 -0.0259 -0.0514 0.046 Uiso 1 1 calc R U . . .
C32 C 0.5487(4) 0.02379(19) -0.12885(13) 0.0421(8) Uani 1 1 d . . . . .
H32 H 0.5434 0.0014 -0.1659 0.050 Uiso 1 1 calc R U . . .
C33 C 0.4195(4) 0.0704(2) -0.11847(17) 0.0591(10) Uani 1 1 d . . . . .
H33A H 0.4121 0.1123 -0.1451 0.071 Uiso 1 1 calc R U . . .
H33B H 0.4233 0.0930 -0.0823 0.071 Uiso 1 1 calc R U . . .
H33C H 0.3398 0.0360 -0.1213 0.071 Uiso 1 1 calc R U . . .
C34 C 0.7477(3) 0.09343(18) -0.16750(12) 0.0375(7) Uani 1 1 d . . . . .
C35 C 0.9750(4) 0.1490(2) -0.18557(14) 0.0481(8) Uani 1 1 d . . . . .
C36 C 1.0232(4) 0.0729(2) -0.21185(19) 0.0708(12) Uani 1 1 d . . . . .
H36A H 0.9591 0.0580 -0.2403 0.085 Uiso 1 1 calc R U . . .
H36B H 1.0269 0.0315 -0.1847 0.085 Uiso 1 1 calc R U . . .
H36C H 1.1145 0.0806 -0.2273 0.085 Uiso 1 1 calc R U . . .
C37 C 0.9362(5) 0.2110(2) -0.22648(14) 0.0618(11) Uani 1 1 d . . . . .
H37A H 0.9201 0.2606 -0.2080 0.074 Uiso 1 1 calc R U . . .
H37B H 0.8527 0.1950 -0.2453 0.074 Uiso 1 1 calc R U . . .
H37C H 1.0107 0.2172 -0.2524 0.074 Uiso 1 1 calc R U . . .
C38 C 1.0824(4) 0.1798(2) -0.14754(16) 0.0602(10) Uani 1 1 d . . . . .
H38A H 1.1083 0.1388 -0.1221 0.072 Uiso 1 1 calc R U . . .
H38B H 1.0455 0.2246 -0.1278 0.072 Uiso 1 1 calc R U . . .
H38C H 1.1631 0.1961 -0.1680 0.072 Uiso 1 1 calc R U . . .
H2 H 0.694(4) 0.094(2) -0.0910(14) 0.052(10) Uiso 1 1 d . . . . .
H10 H 0.889(3) -0.0908(19) 0.0062(13) 0.040(9) Uiso 1 1 d . . . . .
H18 H 0.715(5) 0.099(2) 0.0998(16) 0.067(14) Uiso 1 1 d . . . . .
H26 H 0.857(4) -0.103(2) 0.2063(15) 0.062(12) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2014/8 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.309(4) . ?
O1 C1 1.445(4) . ?
O2 C2 1.201(4) . ?
O3 C10 1.227(4) . ?
O4 C18 1.232(4) . ?
O5 C26 1.228(4) . ?
O6 C34 1.356(4) . ?
O6 C35 1.463(4) . ?
O7 C34 1.227(3) . ?
N1 C10 1.341(4) . ?
N1 C8 1.457(5) . ?
N1 H26 0.86(4) . ?
N2 C18 1.327(4) . ?
N2 C16 1.462(4) . ?
N2 H18 0.77(4) . ?
N3 C26 1.337(4) . ?
N3 C24 1.463(4) . ?
N3 H10 0.93(3) . ?
N4 C34 1.331(4) . ?
N4 C32 1.466(4) . ?
N4 H2 0.96(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.503(5) . ?
C3 C5 1.518(5) . ?
C3 C4 1.536(6) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.509(5) . ?
C5 C7 1.509(5) . ?
C5 H5 1.0000 . ?
C6 C7 1.505(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.501(5) . ?
C7 H7 1.0000 . ?
C8 C9 1.519(5) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.524(5) . ?
C11 C13 1.507(5) . ?
C11 C12 1.540(5) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C15 1.492(5) . ?
C13 C14 1.509(5) . ?
C13 H13 1.0000 . ?
C14 C15 1.500(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.504(4) . ?
C15 H15 1.0000 . ?
C16 C17 1.518(5) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.514(5) . ?
C19 C21 1.508(4) . ?
C19 C20 1.533(5) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C23 1.497(5) . ?
C21 C22 1.503(5) . ?
C21 H21 1.0000 . ?
C22 C23 1.496(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.510(4) . ?
C23 H23 1.0000 . ?
C24 C25 1.516(5) . ?
C24 H24 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.519(5) . ?
C27 C29 1.509(4) . ?
C27 C28 1.532(5) . ?
C27 H27 1.0000 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 C30 1.502(5) . ?
C29 C31 1.505(4) . ?
C29 H29 1.0000 . ?
C30 C31 1.510(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.509(4) . ?
C31 H31 1.0000 . ?
C32 C33 1.517(5) . ?
C32 H32 1.0000 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C35 C38 1.510(5) . ?
C35 C37 1.521(5) . ?
C35 C36 1.533(5) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 116.4(3) . . ?
C34 O6 C35 121.3(2) . . ?
C10 N1 C8 123.0(3) . . ?
C10 N1 H26 117(3) . . ?
C8 N1 H26 119(3) . . ?
C18 N2 C16 124.0(3) . . ?
C18 N2 H18 117(3) . . ?
C16 N2 H18 118(3) . . ?
C26 N3 C24 122.7(3) . . ?
C26 N3 H10 122(2) . . ?
C24 N3 H10 115(2) . . ?
C34 N4 C32 124.6(3) . . ?
C34 N4 H2 119(2) . . ?
C32 N4 H2 117(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 122.5(3) . . ?
O2 C2 C3 123.9(3) . . ?
O1 C2 C3 113.7(3) . . ?
C2 C3 C5 108.3(3) . . ?
C2 C3 C4 110.5(3) . . ?
C5 C3 C4 110.9(3) . . ?
C2 C3 H3 109.1 . . ?
C5 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C7 59.8(2) . . ?
C6 C5 C3 119.1(3) . . ?
C7 C5 C3 121.2(3) . . ?
C6 C5 H5 115.2 . . ?
C7 C5 H5 115.2 . . ?
C3 C5 H5 115.2 . . ?
C7 C6 C5 60.1(2) . . ?
C7 C6 H6A 117.8 . . ?
C5 C6 H6A 117.8 . . ?
C7 C6 H6B 117.8 . . ?
C5 C6 H6B 117.8 . . ?
H6A C6 H6B 114.9 . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 C5 119.9(3) . . ?
C6 C7 C5 60.1(2) . . ?
C8 C7 H7 115.5 . . ?
C6 C7 H7 115.5 . . ?
C5 C7 H7 115.5 . . ?
N1 C8 C7 111.2(3) . . ?
N1 C8 C9 110.0(3) . . ?
C7 C8 C9 111.6(3) . . ?
N1 C8 H8 108.0 . . ?
C7 C8 H8 108.0 . . ?
C9 C8 H8 108.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 N1 123.3(3) . . ?
O3 C10 C11 120.8(3) . . ?
N1 C10 C11 115.8(3) . . ?
C13 C11 C10 111.2(3) . . ?
C13 C11 C12 111.6(4) . . ?
C10 C11 C12 108.0(3) . . ?
C13 C11 H11 108.6 . . ?
C10 C11 H11 108.6 . . ?
C12 C11 H11 108.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C13 C11 120.1(3) . . ?
C15 C13 C14 60.0(2) . . ?
C11 C13 C14 118.2(3) . . ?
C15 C13 H13 115.7 . . ?
C11 C13 H13 115.7 . . ?
C14 C13 H13 115.7 . . ?
C15 C14 C13 59.5(2) . . ?
C15 C14 H14A 117.8 . . ?
C13 C14 H14A 117.8 . . ?
C15 C14 H14B 117.8 . . ?
C13 C14 H14B 117.8 . . ?
H14A C14 H14B 115.0 . . ?
C13 C15 C14 60.6(2) . . ?
C13 C15 C16 120.5(3) . . ?
C14 C15 C16 119.8(3) . . ?
C13 C15 H15 115.0 . . ?
C14 C15 H15 115.0 . . ?
C16 C15 H15 115.0 . . ?
N2 C16 C15 109.2(3) . . ?
N2 C16 C17 111.6(3) . . ?
C15 C16 C17 112.2(3) . . ?
N2 C16 H16 107.9 . . ?
C15 C16 H16 107.9 . . ?
C17 C16 H16 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 N2 122.0(3) . . ?
O4 C18 C19 121.6(3) . . ?
N2 C18 C19 116.4(3) . . ?
C21 C19 C18 109.7(3) . . ?
C21 C19 C20 111.9(3) . . ?
C18 C19 C20 109.4(3) . . ?
C21 C19 H19 108.6 . . ?
C18 C19 H19 108.6 . . ?
C20 C19 H19 108.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 C21 C22 59.8(2) . . ?
C23 C21 C19 120.0(3) . . ?
C22 C21 C19 118.9(3) . . ?
C23 C21 H21 115.6 . . ?
C22 C21 H21 115.6 . . ?
C19 C21 H21 115.6 . . ?
C23 C22 C21 59.9(2) . . ?
C23 C22 H22A 117.8 . . ?
C21 C22 H22A 117.8 . . ?
C23 C22 H22B 117.8 . . ?
C21 C22 H22B 117.8 . . ?
H22A C22 H22B 114.9 . . ?
C22 C23 C21 60.3(2) . . ?
C22 C23 C24 119.5(3) . . ?
C21 C23 C24 119.9(3) . . ?
C22 C23 H23 115.4 . . ?
C21 C23 H23 115.4 . . ?
C24 C23 H23 115.4 . . ?
N3 C24 C23 108.4(3) . . ?
N3 C24 C25 111.2(3) . . ?
C23 C24 C25 112.5(3) . . ?
N3 C24 H24 108.2 . . ?
C23 C24 H24 108.2 . . ?
C25 C24 H24 108.2 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O5 C26 N3 123.2(3) . . ?
O5 C26 C27 120.3(3) . . ?
N3 C26 C27 116.4(3) . . ?
C29 C27 C26 108.2(3) . . ?
C29 C27 C28 111.3(3) . . ?
C26 C27 C28 110.1(3) . . ?
C29 C27 H27 109.1 . . ?
C26 C27 H27 109.1 . . ?
C28 C27 H27 109.1 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 C31 60.3(2) . . ?
C30 C29 C27 122.2(3) . . ?
C31 C29 C27 120.7(3) . . ?
C30 C29 H29 114.4 . . ?
C31 C29 H29 114.4 . . ?
C27 C29 H29 114.4 . . ?
C29 C30 C31 60.0(2) . . ?
C29 C30 H30A 117.8 . . ?
C31 C30 H30A 117.8 . . ?
C29 C30 H30B 117.8 . . ?
C31 C30 H30B 117.8 . . ?
H30A C30 H30B 114.9 . . ?
C29 C31 C32 120.2(3) . . ?
C29 C31 C30 59.8(2) . . ?
C32 C31 C30 121.2(3) . . ?
C29 C31 H31 114.9 . . ?
C32 C31 H31 114.9 . . ?
C30 C31 H31 114.9 . . ?
N4 C32 C31 108.2(3) . . ?
N4 C32 C33 110.9(3) . . ?
C31 C32 C33 112.4(3) . . ?
N4 C32 H32 108.4 . . ?
C31 C32 H32 108.4 . . ?
C33 C32 H32 108.4 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
O7 C34 N4 125.7(3) . . ?
O7 C34 O6 124.7(3) . . ?
N4 C34 O6 109.5(3) . . ?
O6 C35 C38 103.0(3) . . ?
O6 C35 C37 109.6(3) . . ?
C38 C35 C37 110.4(3) . . ?
O6 C35 C36 110.1(3) . . ?
C38 C35 C36 110.6(3) . . ?
C37 C35 C36 112.7(3) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C38 H38A 109.5 . . ?
C35 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C35 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 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
C1 O1 C2 O2 5.6(5) . . . . ?
C1 O1 C2 C3 -174.4(3) . . . . ?
O2 C2 C3 C5 -76.5(5) . . . . ?
O1 C2 C3 C5 103.5(3) . . . . ?
O2 C2 C3 C4 45.0(5) . . . . ?
O1 C2 C3 C4 -135.0(3) . . . . ?
C2 C3 C5 C6 -145.0(3) . . . . ?
C4 C3 C5 C6 93.7(4) . . . . ?
C2 C3 C5 C7 -74.6(4) . . . . ?
C4 C3 C5 C7 164.1(3) . . . . ?
C3 C5 C6 C7 111.3(3) . . . . ?
C5 C6 C7 C8 109.8(3) . . . . ?
C6 C5 C7 C8 -108.3(4) . . . . ?
C3 C5 C7 C8 143.9(3) . . . . ?
C3 C5 C7 C6 -107.8(4) . . . . ?
C10 N1 C8 C7 129.6(3) . . . . ?
C10 N1 C8 C9 -106.3(4) . . . . ?
C6 C7 C8 N1 -154.6(3) . . . . ?
C5 C7 C8 N1 -84.4(4) . . . . ?
C6 C7 C8 C9 82.2(4) . . . . ?
C5 C7 C8 C9 152.3(3) . . . . ?
C8 N1 C10 O3 -7.5(5) . . . . ?
C8 N1 C10 C11 169.9(3) . . . . ?
O3 C10 C11 C13 -55.7(4) . . . . ?
N1 C10 C11 C13 126.8(3) . . . . ?
O3 C10 C11 C12 67.1(5) . . . . ?
N1 C10 C11 C12 -110.3(4) . . . . ?
C10 C11 C13 C15 -88.8(4) . . . . ?
C12 C11 C13 C15 150.5(4) . . . . ?
C10 C11 C13 C14 -158.6(3) . . . . ?
C12 C11 C13 C14 80.7(4) . . . . ?
C11 C13 C14 C15 110.3(4) . . . . ?
C11 C13 C15 C14 -107.2(4) . . . . ?
C11 C13 C15 C16 143.4(3) . . . . ?
C14 C13 C15 C16 -109.3(4) . . . . ?
C13 C14 C15 C16 110.4(3) . . . . ?
C18 N2 C16 C15 136.8(3) . . . . ?
C18 N2 C16 C17 -98.6(4) . . . . ?
C13 C15 C16 N2 -77.6(4) . . . . ?
C14 C15 C16 N2 -149.0(3) . . . . ?
C13 C15 C16 C17 158.2(3) . . . . ?
C14 C15 C16 C17 86.8(4) . . . . ?
C16 N2 C18 O4 0.6(5) . . . . ?
C16 N2 C18 C19 -179.3(3) . . . . ?
O4 C18 C19 C21 -57.1(4) . . . . ?
N2 C18 C19 C21 122.7(3) . . . . ?
O4 C18 C19 C20 66.0(4) . . . . ?
N2 C18 C19 C20 -114.1(3) . . . . ?
C18 C19 C21 C23 -83.9(4) . . . . ?
C20 C19 C21 C23 154.4(3) . . . . ?
C18 C19 C21 C22 -153.8(3) . . . . ?
C20 C19 C21 C22 84.5(4) . . . . ?
C19 C21 C22 C23 109.9(3) . . . . ?
C21 C22 C23 C24 109.7(3) . . . . ?
C19 C21 C23 C22 -108.1(3) . . . . ?
C22 C21 C23 C24 -109.0(3) . . . . ?
C19 C21 C23 C24 142.9(3) . . . . ?
C26 N3 C24 C23 140.1(3) . . . . ?
C26 N3 C24 C25 -95.7(4) . . . . ?
C22 C23 C24 N3 -154.4(3) . . . . ?
C21 C23 C24 N3 -83.8(4) . . . . ?
C22 C23 C24 C25 82.2(4) . . . . ?
C21 C23 C24 C25 152.8(3) . . . . ?
C24 N3 C26 O5 1.3(5) . . . . ?
C24 N3 C26 C27 -177.2(3) . . . . ?
O5 C26 C27 C29 -56.2(4) . . . . ?
N3 C26 C27 C29 122.4(3) . . . . ?
O5 C26 C27 C28 65.7(4) . . . . ?
N3 C26 C27 C28 -115.8(3) . . . . ?
C26 C27 C29 C30 -153.6(3) . . . . ?
C28 C27 C29 C30 85.2(4) . . . . ?
C26 C27 C29 C31 -81.6(3) . . . . ?
C28 C27 C29 C31 157.3(3) . . . . ?
C27 C29 C30 C31 109.6(3) . . . . ?
C30 C29 C31 C32 -110.8(3) . . . . ?
C27 C29 C31 C32 137.3(3) . . . . ?
C27 C29 C31 C30 -111.9(3) . . . . ?
C29 C30 C31 C32 109.1(3) . . . . ?
C34 N4 C32 C31 125.8(3) . . . . ?
C34 N4 C32 C33 -110.6(4) . . . . ?
C29 C31 C32 N4 -86.2(3) . . . . ?
C30 C31 C32 N4 -157.0(3) . . . . ?
C29 C31 C32 C33 151.0(3) . . . . ?
C30 C31 C32 C33 80.2(4) . . . . ?
C32 N4 C34 O7 7.2(5) . . . . ?
C32 N4 C34 O6 -174.2(3) . . . . ?
C35 O6 C34 O7 -14.0(5) . . . . ?
C35 O6 C34 N4 167.4(3) . . . . ?
C34 O6 C35 C38 -169.2(3) . . . . ?
C34 O6 C35 C37 73.3(4) . . . . ?
C34 O6 C35 C36 -51.2(4) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H26 O7 . . 2_655 2.982(4) 0.86(4) 2.15(4) 161(4) no
N2 H18 O2 . . . 2.915(4) 0.77(4) 2.16(4) 169(4) no
N3 H10 O3 . . . 2.935(4) 0.93(3) 2.08(3) 151(3) no
N4 H2 O4 . . . 2.827(3) 0.96(4) 1.94(4) 154(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_nachexamer
_database_code_depnum_ccdc_archive 'CCDC 2049404'
loop_
_audit_author_name
_audit_author_address
'Ryohei Doi'
;Hokkaido University
Japan
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2022-11-18 downloaded from the CCDC.
;
_audit_creation_date             2020-12-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H Cl3, C54 H90 N6 O9'
_chemical_formula_sum            'C55 H91 Cl3 N6 O9'
_chemical_formula_weight         1086.68
_chemical_absolute_configuration ?
_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'
Cl Cl 0.3639 0.7018 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.84115(18)
_cell_length_b                   34.7841(6)
_cell_length_c                   10.17820(18)
_cell_angle_alpha                90
_cell_angle_beta                 117.487(8)
_cell_angle_gamma                90
_cell_volume                     3090.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24800
_cell_measurement_theta_min      4.90
_cell_measurement_theta_max      68.23
_cell_measurement_temperature    133
_shelx_estimated_absorpt_T_max   0.830
_shelx_estimated_absorpt_T_min   0.784
_exptl_absorpt_coefficient_mu    1.779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_T_max  0.824
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1172
_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.109
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            35992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.245
_diffrn_reflns_theta_min         4.898
_diffrn_ambient_temperature      133.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                8495
_reflns_number_total             11242
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 2759 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.075(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     674
_refine_ls_number_reflns         11242
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0677
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+0.4409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1437
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3A), C9(H9), C11(H11), C13(H13), C16(H16), C18(H18),
 C20(H20), C21(H21), C24(H24), C26(H26), C28(H28), C29(H29), C32(H32), C34(H34),
  C36(H36), C37(H37), C40(H40), C42(H42), C44(H44), C47(H47), C49(H49),
 C51(H51), C55(H55)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C19(H19A,H19B), C27(H27A,H27B), C35(H35A,H35B), C43(H43A,
 H43B), C50(H50A,H50B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), N5(H5), N6(H6)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C10(H10A,H10B,H10C),
 C14(H14A,H14B,H14C), C17(H17A,H17B,H17C), C22(H22A,H22B,H22C), C25(H25A,H25B,
 H25C), C30(H30A,H30B,H30C), C33(H33A,H33B,H33C), C38(H38A,H38B,H38C), C41(H41A,
 H41B,H41C), C45(H45A,H45B,H45C), C48(H48A,H48B,H48C), C52(H52A,H52B,H52C),
 C54(H54A,H54B,H54C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.7784(2) 0.01401(5) 0.26524(19) 0.0469(5) Uani 1 1 d . . . . .
Cl2 Cl 0.9820(2) 0.07898(6) 0.3462(2) 0.0623(6) Uani 1 1 d . . . . .
Cl3 Cl 0.7227(2) 0.07581(5) 0.0565(2) 0.0590(5) Uani 1 1 d . . . . .
O1 O 0.4157(5) 0.04450(11) 0.3979(4) 0.0343(11) Uani 1 1 d . . . . .
O2 O 0.2500(4) 0.08551(10) 0.2198(4) 0.0288(10) Uani 1 1 d . . . . .
O3 O 0.6127(5) 0.12347(12) 0.2941(5) 0.0420(12) Uani 1 1 d . . . . .
O4 O 0.2054(5) 0.17558(11) 0.4454(5) 0.0342(11) Uani 1 1 d . . . . .
O5 O 0.5543(6) 0.25845(11) 0.3829(5) 0.0494(14) Uani 1 1 d . . . . .
O6 O 0.0681(5) 0.31492(11) 0.3606(5) 0.0364(11) Uani 1 1 d . . . . .
O7 O 0.5760(5) 0.39982(11) 0.4876(5) 0.0419(12) Uani 1 1 d . . . . .
O8 O 0.1306(5) 0.45245(12) 0.2363(5) 0.0444(13) Uani 1 1 d . . . . .
O9 O 0.2160(5) 0.51272(12) 0.2577(5) 0.0387(11) Uani 1 1 d . . . . .
N1 N 0.3337(6) 0.10028(13) 0.4550(5) 0.0289(12) Uani 1 1 d . . . . .
H1 H 0.259666 0.117452 0.420245 0.035 Uiso 1 1 calc R U . . .
N2 N 0.5114(6) 0.18124(13) 0.2903(5) 0.0267(12) Uani 1 1 d . . . . .
H2 H 0.515261 0.201859 0.342060 0.032 Uiso 1 1 calc R U . . .
N3 N 0.1926(5) 0.24039(13) 0.4584(5) 0.0262(12) Uani 1 1 d . . . . .
H3 H 0.159759 0.261761 0.407022 0.031 Uiso 1 1 calc R U . . .
N4 N 0.5223(5) 0.32253(13) 0.3732(5) 0.0275(12) Uani 1 1 d . . . . .
H4 H 0.530684 0.343697 0.423698 0.033 Uiso 1 1 calc R U . . .
N5 N 0.1126(6) 0.37881(14) 0.3789(5) 0.0287(12) Uani 1 1 d . . . . .
H5 H 0.120220 0.399761 0.334240 0.034 Uiso 1 1 calc R U . . .
N6 N 0.6036(5) 0.46433(13) 0.5111(5) 0.0273(12) Uani 1 1 d . . . . .
H6 H 0.592340 0.485102 0.554443 0.033 Uiso 1 1 calc R U . . .
C1 C 0.6820(7) 0.12907(18) 0.6031(7) 0.0322(15) Uani 1 1 d . . . . .
H1A H 0.695793 0.102082 0.577486 0.039 Uiso 1 1 calc R U . . .
C2 C 0.5460(7) 0.42964(17) 0.6869(7) 0.0307(15) Uani 1 1 d . . . . .
H2A H 0.511936 0.455735 0.700679 0.037 Uiso 1 1 calc R U . . .
C3 C 0.4023(7) 0.45896(17) 0.1591(6) 0.0275(14) Uani 1 1 d . . . . .
H3A H 0.412837 0.431638 0.193025 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1386(8) 0.02429(17) 0.1029(7) 0.0417(18) Uani 1 1 d . . . . .
H4A H 0.203158 0.010095 0.193772 0.050 Uiso 1 1 calc R U . . .
H4B H 0.116182 0.008000 0.016737 0.050 Uiso 1 1 calc R U . . .
H4C H 0.042575 0.031584 0.103218 0.050 Uiso 1 1 calc R U . . .
C5 C 0.3693(7) 0.05153(19) 0.0888(7) 0.0427(18) Uani 1 1 d . . . . .
H5A H 0.429212 0.075215 0.106738 0.051 Uiso 1 1 calc R U . . .
H5B H 0.345654 0.041350 -0.009233 0.051 Uiso 1 1 calc R U . . .
H5C H 0.428604 0.032477 0.164679 0.051 Uiso 1 1 calc R U . . .
C6 C 0.1169(8) 0.08442(19) -0.0368(7) 0.0413(17) Uani 1 1 d . . . . .
H6A H 0.029549 0.093246 -0.023468 0.050 Uiso 1 1 calc R U . . .
H6B H 0.079921 0.069004 -0.127445 0.050 Uiso 1 1 calc R U . . .
H6C H 0.173644 0.106696 -0.044796 0.050 Uiso 1 1 calc R U . . .
C7 C 0.2218(7) 0.06008(16) 0.0952(7) 0.0295(15) Uani 1 1 d . . . . .
C8 C 0.3402(7) 0.07441(17) 0.3600(7) 0.0264(14) Uani 1 1 d . . . . .
C9 C 0.4420(7) 0.10158(17) 0.6124(7) 0.0326(15) Uani 1 1 d . . . . .
H9 H 0.500808 0.076922 0.640554 0.039 Uiso 1 1 calc R U . . .
C10 C 0.3550(8) 0.10584(19) 0.7031(7) 0.0393(17) Uani 1 1 d . . . . .
H10A H 0.287891 0.083562 0.685753 0.047 Uiso 1 1 calc R U . . .
H10B H 0.293208 0.129343 0.673199 0.047 Uiso 1 1 calc R U . . .
H10C H 0.428264 0.107334 0.808604 0.047 Uiso 1 1 calc R U . . .
C11 C 0.5523(7) 0.13422(17) 0.6379(7) 0.0327(15) Uani 1 1 d . . . . .
H11 H 0.503108 0.160164 0.612168 0.039 Uiso 1 1 calc R U . . .
C12 C 0.7129(8) 0.1344(2) 0.7607(8) 0.056(2) Uani 1 1 d . . . . .
H12A H 0.747890 0.111810 0.827168 0.067 Uiso 1 1 calc R U . . .
H12B H 0.756437 0.159326 0.808940 0.067 Uiso 1 1 calc R U . . .
C13 C 0.7226(7) 0.15908(17) 0.5224(7) 0.0304(15) Uani 1 1 d . . . . .
H13 H 0.704760 0.185046 0.553720 0.036 Uiso 1 1 calc R U . . .
C14 C 0.8873(8) 0.1563(2) 0.5517(8) 0.0459(19) Uani 1 1 d . . . . .
H14A H 0.907626 0.176054 0.494401 0.055 Uiso 1 1 calc R U . . .
H14B H 0.905880 0.130811 0.522122 0.055 Uiso 1 1 calc R U . . .
H14C H 0.955168 0.160197 0.657470 0.055 Uiso 1 1 calc R U . . .
C15 C 0.6114(7) 0.15327(17) 0.3571(7) 0.0272(14) Uani 1 1 d . . . . .
C16 C 0.3945(7) 0.17957(17) 0.1346(7) 0.0318(15) Uani 1 1 d . . . . .
H16 H 0.359299 0.152338 0.110024 0.038 Uiso 1 1 calc R U . . .
C17 C 0.4648(8) 0.1922(2) 0.0349(7) 0.0432(18) Uani 1 1 d . . . . .
H17A H 0.498638 0.218970 0.056590 0.052 Uiso 1 1 calc R U . . .
H17B H 0.387986 0.189878 -0.069137 0.052 Uiso 1 1 calc R U . . .
H17C H 0.552750 0.175740 0.053534 0.052 Uiso 1 1 calc R U . . .
C18 C 0.2596(7) 0.20386(17) 0.1153(7) 0.0290(15) Uani 1 1 d . . . . .
H18 H 0.284657 0.231243 0.147311 0.035 Uiso 1 1 calc R U . . .
C19 C 0.1058(7) 0.19764(19) -0.0128(7) 0.0336(16) Uani 1 1 d . . . . .
H19A H 0.094765 0.176611 -0.082624 0.040 Uiso 1 1 calc R U . . .
H19B H 0.041532 0.220541 -0.058731 0.040 Uiso 1 1 calc R U . . .
C20 C 0.1346(7) 0.18682(17) 0.1402(6) 0.0272(14) Uani 1 1 d . . . . .
H20 H 0.144241 0.158590 0.161249 0.033 Uiso 1 1 calc R U . . .
C21 C 0.0608(7) 0.20967(17) 0.2178(7) 0.0303(15) Uani 1 1 d . . . . .
H21 H 0.054903 0.237243 0.187828 0.036 Uiso 1 1 calc R U . . .
C22 C -0.1005(7) 0.1955(2) 0.1764(7) 0.0410(18) Uani 1 1 d . . . . .
H22A H -0.144123 0.211029 0.228164 0.049 Uiso 1 1 calc R U . . .
H22B H -0.096472 0.168525 0.205262 0.049 Uiso 1 1 calc R U . . .
H22C H -0.164685 0.198002 0.069227 0.049 Uiso 1 1 calc R U . . .
C23 C 0.1591(7) 0.20693(16) 0.3835(7) 0.0252(14) Uani 1 1 d . . . . .
C24 C 0.2792(7) 0.24356(16) 0.6183(6) 0.0265(14) Uani 1 1 d . . . . .
H24 H 0.328512 0.218149 0.658176 0.032 Uiso 1 1 calc R U . . .
C25 C 0.1737(7) 0.25301(19) 0.6861(7) 0.0388(17) Uani 1 1 d . . . . .
H25A H 0.234124 0.254845 0.793932 0.047 Uiso 1 1 calc R U . . .
H25B H 0.096814 0.232675 0.661170 0.047 Uiso 1 1 calc R U . . .
H25C H 0.122366 0.277598 0.646659 0.047 Uiso 1 1 calc R U . . .
C26 C 0.4041(7) 0.27326(17) 0.6597(7) 0.0296(15) Uani 1 1 d . . . . .
H26 H 0.367565 0.299962 0.624767 0.035 Uiso 1 1 calc R U . . .
C27 C 0.5459(8) 0.2707(2) 0.8072(7) 0.0441(18) Uani 1 1 d . . . . .
H27A H 0.590615 0.295002 0.860242 0.053 Uiso 1 1 calc R U . . .
H27B H 0.555236 0.248517 0.871785 0.053 Uiso 1 1 calc R U . . .
C28 C 0.5544(7) 0.26301(17) 0.6664(6) 0.0283(14) Uani 1 1 d . . . . .
H28 H 0.565660 0.235276 0.647467 0.034 Uiso 1 1 calc R U . . .
C29 C 0.6390(7) 0.29076(17) 0.6139(7) 0.0288(15) Uani 1 1 d . . . . .
H29 H 0.629174 0.317421 0.645339 0.035 Uiso 1 1 calc R U . . .
C30 C 0.8086(7) 0.28060(19) 0.6775(7) 0.0391(17) Uani 1 1 d . . . . .
H30A H 0.819026 0.255056 0.642587 0.047 Uiso 1 1 calc R U . . .
H30B H 0.855600 0.280576 0.785918 0.047 Uiso 1 1 calc R U . . .
H30C H 0.859878 0.299661 0.644810 0.047 Uiso 1 1 calc R U . . .
C31 C 0.5654(7) 0.28924(18) 0.4450(7) 0.0300(15) Uani 1 1 d . . . . .
C32 C 0.4618(7) 0.32483(17) 0.2133(7) 0.0310(15) Uani 1 1 d . . . . .
H32 H 0.443936 0.298049 0.173015 0.037 Uiso 1 1 calc R U . . .
C33 C 0.5785(8) 0.3438(2) 0.1754(8) 0.0481(19) Uani 1 1 d . . . . .
H33A H 0.593896 0.370543 0.209655 0.058 Uiso 1 1 calc R U . . .
H33B H 0.540861 0.343214 0.067964 0.058 Uiso 1 1 calc R U . . .
H33C H 0.675885 0.329896 0.224331 0.058 Uiso 1 1 calc R U . . .
C34 C 0.3101(7) 0.34583(17) 0.1443(7) 0.0287(14) Uani 1 1 d . . . . .
H34 H 0.315354 0.373910 0.167314 0.034 Uiso 1 1 calc R U . . .
C35 C 0.1917(7) 0.33447(18) -0.0087(7) 0.0356(16) Uani 1 1 d . . . . .
H35A H 0.215795 0.312697 -0.057023 0.043 Uiso 1 1 calc R U . . .
H35B H 0.129311 0.355137 -0.076605 0.043 Uiso 1 1 calc R U . . .
C36 C 0.1669(7) 0.32577(17) 0.1240(7) 0.0291(14) Uani 1 1 d . . . . .
H36 H 0.179769 0.298219 0.155498 0.035 Uiso 1 1 calc R U . . .
C37 C 0.0443(7) 0.34751(16) 0.1429(6) 0.0248(13) Uani 1 1 d . . . . .
H37 H 0.046016 0.375025 0.115157 0.030 Uiso 1 1 calc R U . . .
C38 C -0.1150(7) 0.33081(18) 0.0452(7) 0.0340(16) Uani 1 1 d . . . . .
H38A H -0.117524 0.303812 0.071540 0.041 Uiso 1 1 calc R U . . .
H38B H -0.137864 0.332564 -0.059037 0.041 Uiso 1 1 calc R U . . .
H38C H -0.191710 0.345376 0.060710 0.041 Uiso 1 1 calc R U . . .
C39 C 0.0763(6) 0.34554(17) 0.3040(7) 0.0264(14) Uani 1 1 d . . . . .
C40 C 0.1402(7) 0.38129(17) 0.5333(7) 0.0284(14) Uani 1 1 d . . . . .
H40 H 0.178777 0.355692 0.580600 0.034 Uiso 1 1 calc R U . . .
C41 C -0.0091(8) 0.3894(2) 0.5388(8) 0.0483(19) Uani 1 1 d . . . . .
H41A H -0.050689 0.414115 0.491192 0.058 Uiso 1 1 calc R U . . .
H41B H 0.010260 0.390272 0.642284 0.058 Uiso 1 1 calc R U . . .
H41C H -0.083010 0.368920 0.486656 0.058 Uiso 1 1 calc R U . . .
C42 C 0.2622(7) 0.41060(17) 0.6170(7) 0.0298(15) Uani 1 1 d . . . . .
H42 H 0.234435 0.437969 0.586278 0.036 Uiso 1 1 calc R U . . .
C43 C 0.3610(7) 0.4039(2) 0.7788(7) 0.0379(17) Uani 1 1 d . . . . .
H43A H 0.390892 0.426553 0.845242 0.045 Uiso 1 1 calc R U . . .
H43B H 0.344891 0.379978 0.822301 0.045 Uiso 1 1 calc R U . . .
C44 C 0.4265(7) 0.40045(17) 0.6731(6) 0.0273(14) Uani 1 1 d . . . . .
H44 H 0.446394 0.373563 0.651667 0.033 Uiso 1 1 calc R U . . .
C45 C 0.6992(8) 0.4201(2) 0.8216(8) 0.0484(19) Uani 1 1 d . . . . .
H45A H 0.735973 0.395132 0.806513 0.058 Uiso 1 1 calc R U . . .
H45B H 0.684905 0.419084 0.910618 0.058 Uiso 1 1 calc R U . . .
H45C H 0.774511 0.440019 0.833577 0.058 Uiso 1 1 calc R U . . .
C46 C 0.5731(7) 0.43025(18) 0.5510(7) 0.0313(15) Uani 1 1 d . . . . .
C47 C 0.6552(7) 0.46867(16) 0.3976(7) 0.0302(15) Uani 1 1 d . . . . .
H47 H 0.682878 0.442564 0.376402 0.036 Uiso 1 1 calc R U . . .
C48 C 0.7991(7) 0.49307(19) 0.4605(7) 0.0397(17) Uani 1 1 d . . . . .
H48A H 0.839364 0.494448 0.388756 0.048 Uiso 1 1 calc R U . . .
H48B H 0.876102 0.481500 0.552700 0.048 Uiso 1 1 calc R U . . .
H48C H 0.774743 0.519028 0.480721 0.048 Uiso 1 1 calc R U . . .
C49 C 0.5316(7) 0.48429(16) 0.2564(7) 0.0279(14) Uani 1 1 d . . . . .
H49 H 0.503779 0.511766 0.260264 0.033 Uiso 1 1 calc R U . . .
C50 C 0.5184(7) 0.47131(18) 0.1103(7) 0.0393(17) Uani 1 1 d . . . . .
H50A H 0.592340 0.451848 0.111384 0.047 Uiso 1 1 calc R U . . .
H50B H 0.486400 0.490521 0.029653 0.047 Uiso 1 1 calc R U . . .
C51 C 0.2386(7) 0.47340(16) 0.0804(7) 0.0295(15) Uani 1 1 d . . . . .
H51 H 0.239008 0.499458 0.039096 0.035 Uiso 1 1 calc R U . . .
C52 C 0.1353(7) 0.44771(17) -0.0454(7) 0.0333(16) Uani 1 1 d . . . . .
H52A H 0.126548 0.422622 -0.006184 0.040 Uiso 1 1 calc R U . . .
H52B H 0.178503 0.444343 -0.114244 0.040 Uiso 1 1 calc R U . . .
H52C H 0.033571 0.459470 -0.097712 0.040 Uiso 1 1 calc R U . . .
C53 C 0.1856(7) 0.47760(17) 0.1960(7) 0.0288(15) Uani 1 1 d . . . . .
C54 C 0.1914(9) 0.5183(2) 0.3859(8) 0.0484(19) Uani 1 1 d . . . . .
H54A H 0.290433 0.518845 0.475456 0.058 Uiso 1 1 calc R U . . .
H54B H 0.129487 0.497050 0.392837 0.058 Uiso 1 1 calc R U . . .
H54C H 0.137724 0.542633 0.376387 0.058 Uiso 1 1 calc R U . . .
C55 C 0.7945(8) 0.0637(2) 0.2444(7) 0.0470(19) Uani 1 1 d . . . . .
H55 H 0.730881 0.077247 0.283324 0.056 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
Cl1 C55 1.758(7) . ?
Cl2 C55 1.731(7) . ?
Cl3 C55 1.757(7) . ?
O1 C8 1.232(6) . ?
O2 C7 1.464(7) . ?
O2 C8 1.344(7) . ?
O3 C15 1.223(7) . ?
O4 C23 1.236(6) . ?
O5 C31 1.223(7) . ?
O6 C39 1.231(6) . ?
O7 C46 1.247(7) . ?
O8 C53 1.197(7) . ?
O9 C53 1.343(7) . ?
O9 C54 1.446(7) . ?
N1 H1 0.8800 . ?
N1 C8 1.344(7) . ?
N1 C9 1.459(7) . ?
N2 H2 0.8800 . ?
N2 C15 1.326(7) . ?
N2 C16 1.468(8) . ?
N3 H3 0.8800 . ?
N3 C23 1.346(7) . ?
N3 C24 1.451(7) . ?
N4 H4 0.8800 . ?
N4 C31 1.330(7) . ?
N4 C32 1.454(7) . ?
N5 H5 0.8800 . ?
N5 C39 1.340(7) . ?
N5 C40 1.469(7) . ?
N6 H6 0.8800 . ?
N6 C46 1.331(7) . ?
N6 C47 1.468(7) . ?
C1 H1A 1.0000 . ?
C1 C11 1.485(8) . ?
C1 C12 1.500(9) . ?
C1 C13 1.492(8) . ?
C2 H2A 1.0000 . ?
C2 C44 1.511(8) . ?
C2 C45 1.534(9) . ?
C2 C46 1.524(8) . ?
C3 H3A 1.0000 . ?
C3 C49 1.488(8) . ?
C3 C50 1.504(9) . ?
C3 C51 1.517(8) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C7 1.512(8) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C5 C7 1.512(9) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C6 C7 1.519(8) . ?
C9 H9 1.0000 . ?
C9 C10 1.529(8) . ?
C9 C11 1.508(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.496(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 1.0000 . ?
C13 C14 1.509(9) . ?
C13 C15 1.540(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.532(8) . ?
C16 C18 1.508(8) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18 1.0000 . ?
C18 C19 1.489(9) . ?
C18 C20 1.490(8) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.497(8) . ?
C20 H20 1.0000 . ?
C20 C21 1.520(8) . ?
C21 H21 1.0000 . ?
C21 C22 1.524(8) . ?
C21 C23 1.511(9) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C24 H24 1.0000 . ?
C24 C25 1.524(8) . ?
C24 C26 1.509(8) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26 1.0000 . ?
C26 C27 1.509(9) . ?
C26 C28 1.493(8) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.498(8) . ?
C28 H28 1.0000 . ?
C28 C29 1.523(8) . ?
C29 H29 1.0000 . ?
C29 C30 1.527(8) . ?
C29 C31 1.527(8) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C32 H32 1.0000 . ?
C32 C33 1.520(8) . ?
C32 C34 1.512(8) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34 1.0000 . ?
C34 C35 1.505(8) . ?
C34 C36 1.499(8) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.509(8) . ?
C36 H36 1.0000 . ?
C36 C37 1.509(8) . ?
C37 H37 1.0000 . ?
C37 C38 1.532(8) . ?
C37 C39 1.522(8) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C40 H40 1.0000 . ?
C40 C41 1.523(9) . ?
C40 C42 1.504(8) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C42 H42 1.0000 . ?
C42 C43 1.495(8) . ?
C42 C44 1.488(8) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 C44 1.492(8) . ?
C44 H44 1.0000 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C47 H47 1.0000 . ?
C47 C48 1.516(8) . ?
C47 C49 1.492(8) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49 1.0000 . ?
C49 C50 1.501(8) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 H51 1.0000 . ?
C51 C52 1.507(8) . ?
C51 C53 1.498(8) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 H55 1.0000 . ?

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
C8 O2 C7 121.0(4) . . ?
C53 O9 C54 116.7(5) . . ?
C8 N1 H1 118.1 . . ?
C8 N1 C9 123.9(5) . . ?
C9 N1 H1 118.1 . . ?
C15 N2 H2 118.3 . . ?
C15 N2 C16 123.4(5) . . ?
C16 N2 H2 118.3 . . ?
C23 N3 H3 117.8 . . ?
C23 N3 C24 124.3(5) . . ?
C24 N3 H3 117.8 . . ?
C31 N4 H4 119.2 . . ?
C31 N4 C32 121.7(5) . . ?
C32 N4 H4 119.2 . . ?
C39 N5 H5 119.1 . . ?
C39 N5 C40 121.9(5) . . ?
C40 N5 H5 119.1 . . ?
C46 N6 H6 118.7 . . ?
C46 N6 C47 122.7(5) . . ?
C47 N6 H6 118.7 . . ?
C11 C1 H1A 114.2 . . ?
C11 C1 C12 60.1(4) . . ?
C11 C1 C13 121.7(5) . . ?
C12 C1 H1A 114.2 . . ?
C13 C1 H1A 114.2 . . ?
C13 C1 C12 121.9(6) . . ?
C44 C2 H2A 109.0 . . ?
C44 C2 C45 109.8(5) . . ?
C44 C2 C46 112.3(5) . . ?
C45 C2 H2A 109.0 . . ?
C46 C2 H2A 109.0 . . ?
C46 C2 C45 107.6(5) . . ?
C49 C3 H3A 114.4 . . ?
C49 C3 C50 60.2(4) . . ?
C49 C3 C51 122.0(5) . . ?
C50 C3 H3A 114.4 . . ?
C50 C3 C51 121.0(5) . . ?
C51 C3 H3A 114.4 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C7 C4 H4A 109.5 . . ?
C7 C4 H4B 109.5 . . ?
C7 C4 H4C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C5 H5A 109.5 . . ?
C7 C5 H5B 109.5 . . ?
C7 C5 H5C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
O2 C7 C4 110.0(5) . . ?
O2 C7 C5 110.8(5) . . ?
O2 C7 C6 102.1(5) . . ?
C4 C7 C5 113.2(5) . . ?
C4 C7 C6 110.0(5) . . ?
C5 C7 C6 110.2(6) . . ?
O1 C8 O2 125.6(6) . . ?
O1 C8 N1 124.2(6) . . ?
O2 C8 N1 110.1(5) . . ?
N1 C9 H9 108.7 . . ?
N1 C9 C10 109.7(5) . . ?
N1 C9 C11 108.4(5) . . ?
C10 C9 H9 108.7 . . ?
C11 C9 H9 108.7 . . ?
C11 C9 C10 112.5(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C11 C9 119.8(5) . . ?
C1 C11 H11 114.3 . . ?
C1 C11 C12 60.4(4) . . ?
C9 C11 H11 114.3 . . ?
C12 C11 C9 123.1(6) . . ?
C12 C11 H11 114.3 . . ?
C1 C12 H12A 117.8 . . ?
C1 C12 H12B 117.8 . . ?
C11 C12 C1 59.4(4) . . ?
C11 C12 H12A 117.8 . . ?
C11 C12 H12B 117.8 . . ?
H12A C12 H12B 115.0 . . ?
C1 C13 H13 109.0 . . ?
C1 C13 C14 112.5(5) . . ?
C1 C13 C15 105.9(5) . . ?
C14 C13 H13 109.0 . . ?
C14 C13 C15 111.4(5) . . ?
C15 C13 H13 109.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 N2 122.6(6) . . ?
O3 C15 C13 120.7(6) . . ?
N2 C15 C13 116.7(5) . . ?
N2 C16 H16 108.4 . . ?
N2 C16 C17 109.6(5) . . ?
N2 C16 C18 108.8(5) . . ?
C17 C16 H16 108.4 . . ?
C18 C16 H16 108.4 . . ?
C18 C16 C17 113.1(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18 114.9 . . ?
C19 C18 C16 120.7(5) . . ?
C19 C18 H18 114.9 . . ?
C19 C18 C20 60.4(4) . . ?
C20 C18 C16 120.1(5) . . ?
C20 C18 H18 114.9 . . ?
C18 C19 H19A 117.8 . . ?
C18 C19 H19B 117.8 . . ?
C18 C19 C20 59.8(4) . . ?
H19A C19 H19B 114.9 . . ?
C20 C19 H19A 117.8 . . ?
C20 C19 H19B 117.8 . . ?
C18 C20 C19 59.8(4) . . ?
C18 C20 H20 115.0 . . ?
C18 C20 C21 120.7(5) . . ?
C19 C20 H20 115.0 . . ?
C19 C20 C21 120.2(5) . . ?
C21 C20 H20 115.0 . . ?
C20 C21 H21 108.5 . . ?
C20 C21 C22 112.0(5) . . ?
C22 C21 H21 108.5 . . ?
C23 C21 C20 109.5(5) . . ?
C23 C21 H21 108.5 . . ?
C23 C21 C22 109.6(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 C23 N3 122.5(6) . . ?
O4 C23 C21 121.3(5) . . ?
N3 C23 C21 116.2(5) . . ?
N3 C24 H24 108.2 . . ?
N3 C24 C25 110.7(5) . . ?
N3 C24 C26 110.2(5) . . ?
C25 C24 H24 108.2 . . ?
C26 C24 H24 108.2 . . ?
C26 C24 C25 111.3(5) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26 115.1 . . ?
C27 C26 C24 119.8(5) . . ?
C27 C26 H26 115.1 . . ?
C28 C26 C24 120.8(5) . . ?
C28 C26 H26 115.1 . . ?
C28 C26 C27 59.9(4) . . ?
C26 C27 H27A 117.8 . . ?
C26 C27 H27B 117.8 . . ?
H27A C27 H27B 115.0 . . ?
C28 C27 C26 59.5(4) . . ?
C28 C27 H27A 117.8 . . ?
C28 C27 H27B 117.8 . . ?
C26 C28 C27 60.6(4) . . ?
C26 C28 H28 114.6 . . ?
C26 C28 C29 121.5(5) . . ?
C27 C28 H28 114.6 . . ?
C27 C28 C29 120.2(5) . . ?
C29 C28 H28 114.6 . . ?
C28 C29 H29 109.1 . . ?
C28 C29 C30 111.8(5) . . ?
C28 C29 C31 108.7(5) . . ?
C30 C29 H29 109.1 . . ?
C30 C29 C31 109.0(5) . . ?
C31 C29 H29 109.1 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O5 C31 N4 123.3(6) . . ?
O5 C31 C29 119.7(6) . . ?
N4 C31 C29 117.0(5) . . ?
N4 C32 H32 108.1 . . ?
N4 C32 C33 109.9(5) . . ?
N4 C32 C34 110.7(5) . . ?
C33 C32 H32 108.1 . . ?
C34 C32 H32 108.1 . . ?
C34 C32 C33 111.8(5) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34 115.5 . . ?
C35 C34 C32 118.7(5) . . ?
C35 C34 H34 115.5 . . ?
C36 C34 C32 120.2(5) . . ?
C36 C34 H34 115.5 . . ?
C36 C34 C35 60.3(4) . . ?
C34 C35 H35A 117.8 . . ?
C34 C35 H35B 117.8 . . ?
C34 C35 C36 59.7(4) . . ?
H35A C35 H35B 114.9 . . ?
C36 C35 H35A 117.8 . . ?
C36 C35 H35B 117.8 . . ?
C34 C36 C35 60.0(4) . . ?
C34 C36 H36 115.5 . . ?
C34 C36 C37 120.3(5) . . ?
C35 C36 H36 115.5 . . ?
C37 C36 C35 118.8(5) . . ?
C37 C36 H36 115.5 . . ?
C36 C37 H37 109.0 . . ?
C36 C37 C38 111.5(5) . . ?
C36 C37 C39 109.6(5) . . ?
C38 C37 H37 109.0 . . ?
C39 C37 H37 109.0 . . ?
C39 C37 C38 108.8(5) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O6 C39 N5 122.6(6) . . ?
O6 C39 C37 121.2(5) . . ?
N5 C39 C37 116.2(5) . . ?
N5 C40 H40 107.7 . . ?
N5 C40 C41 110.2(5) . . ?
N5 C40 C42 110.6(5) . . ?
C41 C40 H40 107.7 . . ?
C42 C40 H40 107.7 . . ?
C42 C40 C41 112.7(5) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C40 C42 H42 115.9 . . ?
C43 C42 C40 117.5(5) . . ?
C43 C42 H42 115.9 . . ?
C44 C42 C40 119.9(5) . . ?
C44 C42 H42 115.9 . . ?
C44 C42 C43 60.0(4) . . ?
C42 C43 H43A 117.8 . . ?
C42 C43 H43B 117.8 . . ?
H43A C43 H43B 114.9 . . ?
C44 C43 C42 59.7(4) . . ?
C44 C43 H43A 117.8 . . ?
C44 C43 H43B 117.8 . . ?
C2 C44 H44 115.2 . . ?
C42 C44 C2 122.6(5) . . ?
C42 C44 C43 60.2(4) . . ?
C42 C44 H44 115.2 . . ?
C43 C44 C2 117.1(5) . . ?
C43 C44 H44 115.2 . . ?
C2 C45 H45A 109.5 . . ?
C2 C45 H45B 109.5 . . ?
C2 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O7 C46 N6 122.4(6) . . ?
O7 C46 C2 120.9(6) . . ?
N6 C46 C2 116.6(5) . . ?
N6 C47 H47 107.7 . . ?
N6 C47 C48 108.7(5) . . ?
N6 C47 C49 111.8(5) . . ?
C48 C47 H47 107.7 . . ?
C49 C47 H47 107.7 . . ?
C49 C47 C48 112.9(5) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C3 C49 C47 119.5(5) . . ?
C3 C49 H49 115.2 . . ?
C3 C49 C50 60.4(4) . . ?
C47 C49 H49 115.2 . . ?
C47 C49 C50 120.3(5) . . ?
C50 C49 H49 115.2 . . ?
C3 C50 H50A 117.8 . . ?
C3 C50 H50B 117.8 . . ?
C49 C50 C3 59.4(4) . . ?
C49 C50 H50A 117.8 . . ?
C49 C50 H50B 117.8 . . ?
H50A C50 H50B 115.0 . . ?
C3 C51 H51 108.2 . . ?
C52 C51 C3 112.8(5) . . ?
C52 C51 H51 108.2 . . ?
C53 C51 C3 106.7(5) . . ?
C53 C51 H51 108.2 . . ?
C53 C51 C52 112.5(5) . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52B 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
O8 C53 O9 122.9(6) . . ?
O8 C53 C51 125.1(6) . . ?
O9 C53 C51 111.9(5) . . ?
O9 C54 H54A 109.5 . . ?
O9 C54 H54B 109.5 . . ?
O9 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
Cl1 C55 H55 107.9 . . ?
Cl2 C55 Cl1 111.1(4) . . ?
Cl2 C55 Cl3 111.1(4) . . ?
Cl2 C55 H55 107.9 . . ?
Cl3 C55 Cl1 110.7(4) . . ?
Cl3 C55 H55 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C9 C11 C1 -79.5(7) . . . . ?
N1 C9 C11 C12 -151.8(6) . . . . ?
N2 C16 C18 C19 -159.0(5) . . . . ?
N2 C16 C18 C20 -87.7(7) . . . . ?
N3 C24 C26 C27 -154.4(5) . . . . ?
N3 C24 C26 C28 -83.8(7) . . . . ?
N4 C32 C34 C35 -148.0(5) . . . . ?
N4 C32 C34 C36 -77.5(7) . . . . ?
N5 C40 C42 C43 -149.1(5) . . . . ?
N5 C40 C42 C44 -79.6(7) . . . . ?
N6 C47 C49 C3 -74.2(7) . . . . ?
N6 C47 C49 C50 -145.1(5) . . . . ?
C1 C13 C15 O3 -63.1(7) . . . . ?
C1 C13 C15 N2 113.9(6) . . . . ?
C3 C51 C53 O8 -86.4(7) . . . . ?
C3 C51 C53 O9 89.6(6) . . . . ?
C7 O2 C8 O1 5.9(8) . . . . ?
C7 O2 C8 N1 -172.4(4) . . . . ?
C8 O2 C7 C4 63.4(7) . . . . ?
C8 O2 C7 C5 -62.5(7) . . . . ?
C8 O2 C7 C6 -179.8(5) . . . . ?
C8 N1 C9 C10 -133.5(6) . . . . ?
C8 N1 C9 C11 103.4(6) . . . . ?
C9 N1 C8 O1 15.9(9) . . . . ?
C9 N1 C8 O2 -165.7(5) . . . . ?
C9 C11 C12 C1 108.2(7) . . . . ?
C10 C9 C11 C1 159.0(5) . . . . ?
C10 C9 C11 C12 86.8(8) . . . . ?
C11 C1 C13 C14 156.8(6) . . . . ?
C11 C1 C13 C15 -81.4(7) . . . . ?
C12 C1 C11 C9 -113.5(7) . . . . ?
C12 C1 C13 C14 84.6(7) . . . . ?
C12 C1 C13 C15 -153.6(6) . . . . ?
C13 C1 C11 C9 135.3(6) . . . . ?
C13 C1 C11 C12 -111.2(7) . . . . ?
C13 C1 C12 C11 110.9(6) . . . . ?
C14 C13 C15 O3 59.4(8) . . . . ?
C14 C13 C15 N2 -123.5(6) . . . . ?
C15 N2 C16 C17 -83.4(7) . . . . ?
C15 N2 C16 C18 152.4(5) . . . . ?
C16 N2 C15 O3 -1.0(9) . . . . ?
C16 N2 C15 C13 -178.0(5) . . . . ?
C16 C18 C19 C20 109.4(6) . . . . ?
C16 C18 C20 C19 -110.5(6) . . . . ?
C16 C18 C20 C21 140.2(6) . . . . ?
C17 C16 C18 C19 79.0(7) . . . . ?
C17 C16 C18 C20 150.3(6) . . . . ?
C18 C19 C20 C21 110.2(6) . . . . ?
C18 C20 C21 C22 155.8(6) . . . . ?
C18 C20 C21 C23 -82.3(7) . . . . ?
C19 C18 C20 C21 -109.3(6) . . . . ?
C19 C20 C21 C22 85.2(7) . . . . ?
C19 C20 C21 C23 -153.0(5) . . . . ?
C20 C21 C23 O4 -49.5(7) . . . . ?
C20 C21 C23 N3 130.4(5) . . . . ?
C22 C21 C23 O4 73.7(7) . . . . ?
C22 C21 C23 N3 -106.4(6) . . . . ?
C23 N3 C24 C25 -105.3(6) . . . . ?
C23 N3 C24 C26 131.1(6) . . . . ?
C24 N3 C23 O4 -3.0(9) . . . . ?
C24 N3 C23 C21 177.1(5) . . . . ?
C24 C26 C27 C28 110.4(6) . . . . ?
C24 C26 C28 C27 -108.9(6) . . . . ?
C24 C26 C28 C29 141.7(6) . . . . ?
C25 C24 C26 C27 82.3(7) . . . . ?
C25 C24 C26 C28 152.9(6) . . . . ?
C26 C27 C28 C29 111.5(6) . . . . ?
C26 C28 C29 C30 160.7(5) . . . . ?
C26 C28 C29 C31 -78.9(7) . . . . ?
C27 C26 C28 C29 -109.4(7) . . . . ?
C27 C28 C29 C30 88.7(7) . . . . ?
C27 C28 C29 C31 -150.8(6) . . . . ?
C28 C29 C31 O5 -55.5(7) . . . . ?
C28 C29 C31 N4 127.3(6) . . . . ?
C30 C29 C31 O5 66.6(7) . . . . ?
C30 C29 C31 N4 -110.5(6) . . . . ?
C31 N4 C32 C33 -108.4(6) . . . . ?
C31 N4 C32 C34 127.7(6) . . . . ?
C32 N4 C31 O5 -1.7(9) . . . . ?
C32 N4 C31 C29 175.3(5) . . . . ?
C32 C34 C35 C36 110.3(6) . . . . ?
C32 C34 C36 C35 -108.0(6) . . . . ?
C32 C34 C36 C37 144.1(6) . . . . ?
C33 C32 C34 C35 89.2(7) . . . . ?
C33 C32 C34 C36 159.6(6) . . . . ?
C34 C35 C36 C37 110.4(6) . . . . ?
C34 C36 C37 C38 150.2(5) . . . . ?
C34 C36 C37 C39 -89.3(6) . . . . ?
C35 C34 C36 C37 -107.9(6) . . . . ?
C35 C36 C37 C38 80.0(7) . . . . ?
C35 C36 C37 C39 -159.5(5) . . . . ?
C36 C37 C39 O6 -66.7(7) . . . . ?
C36 C37 C39 N5 113.6(6) . . . . ?
C38 C37 C39 O6 55.4(7) . . . . ?
C38 C37 C39 N5 -124.3(6) . . . . ?
C39 N5 C40 C41 -89.2(7) . . . . ?
C39 N5 C40 C42 145.6(6) . . . . ?
C40 N5 C39 O6 -2.2(9) . . . . ?
C40 N5 C39 C37 177.5(5) . . . . ?
C40 C42 C43 C44 110.4(6) . . . . ?
C40 C42 C44 C2 148.6(6) . . . . ?
C40 C42 C44 C43 -106.5(6) . . . . ?
C41 C40 C42 C43 87.1(7) . . . . ?
C41 C40 C42 C44 156.6(6) . . . . ?
C42 C43 C44 C2 113.8(6) . . . . ?
C43 C42 C44 C2 -104.9(6) . . . . ?
C44 C2 C46 O7 -39.7(8) . . . . ?
C44 C2 C46 N6 144.7(5) . . . . ?
C45 C2 C44 C42 146.0(6) . . . . ?
C45 C2 C44 C43 75.6(7) . . . . ?
C45 C2 C46 O7 81.3(7) . . . . ?
C45 C2 C46 N6 -94.2(6) . . . . ?
C46 N6 C47 C48 -128.3(6) . . . . ?
C46 N6 C47 C49 106.3(6) . . . . ?
C46 C2 C44 C42 -94.3(7) . . . . ?
C46 C2 C44 C43 -164.7(5) . . . . ?
C47 N6 C46 O7 -5.1(9) . . . . ?
C47 N6 C46 C2 170.3(5) . . . . ?
C47 C49 C50 C3 108.8(6) . . . . ?
C48 C47 C49 C3 162.8(5) . . . . ?
C48 C47 C49 C50 91.9(7) . . . . ?
C49 C3 C51 C52 162.5(5) . . . . ?
C49 C3 C51 C53 -73.4(7) . . . . ?
C50 C3 C49 C47 -110.2(6) . . . . ?
C50 C3 C51 C52 90.4(7) . . . . ?
C50 C3 C51 C53 -145.5(6) . . . . ?
C51 C3 C49 C47 139.7(6) . . . . ?
C51 C3 C49 C50 -110.0(6) . . . . ?
C51 C3 C50 C49 111.6(6) . . . . ?
C52 C51 C53 O8 37.9(9) . . . . ?
C52 C51 C53 O9 -146.1(5) . . . . ?
C54 O9 C53 O8 5.2(9) . . . . ?
C54 O9 C53 C51 -170.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


