# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_80717su
_database_code_depnum_ccdc_archive 'CCDC 2014517'
loop_
_audit_author_name
_audit_author_address
'Takayuki Tanaka'
;Kyoto University
Japan
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 N3 O12'
_chemical_formula_sum            'C21 H21 N3 O12'
_chemical_formula_weight         507.41

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   28.349(11)
_cell_length_b                   9.848(3)
_cell_length_c                   19.498(7)
_cell_angle_alpha                90
_cell_angle_beta                 124.168(5)
_cell_angle_gamma                90
_cell_volume                     4504(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1170
_cell_measurement_theta_min      30.9
_cell_measurement_theta_max      72.4

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.078
_shelx_estimated_absorpt_T_min   0.767
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            14677
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.769
_diffrn_reflns_theta_max         66.997
_diffrn_reflns_theta_full        66.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3969
_reflns_number_gt                2636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0700P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3969
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1301
_refine_ls_wR_factor_gt          0.1190
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.15920(8) 0.6984(2) 0.08275(11) 0.0223(4) Uani 1 1 d . . . . .
H19 H 0.1243 0.7311 0.0536 0.027 Uiso 1 1 calc R U . . .
O1 O 0.35647(7) 0.68498(18) 0.15385(10) 0.0279(4) Uani 1 1 d . . . . .
O2 O 0.18201(8) 0.33121(19) 0.20890(11) 0.0325(4) Uani 1 1 d . . . . .
O7 O 0.09514(7) 0.34524(17) 0.17990(10) 0.0272(4) Uani 1 1 d . . . . .
O3 O 0.05397(7) 0.68169(18) 0.04536(10) 0.0280(4) Uani 1 1 d . . . . .
O4 O 0.29595(7) 0.33386(19) 0.25173(10) 0.0323(4) Uani 1 1 d . . . . .
N2 N 0.22303(8) 0.5333(2) 0.16886(11) 0.0232(4) Uani 1 1 d . . . . .
H20 H 0.2306 0.4587 0.1981 0.028 Uiso 1 1 calc R U . . .
N3 N 0.25248(8) 0.7047(2) 0.12023(11) 0.0223(4) Uani 1 1 d . . . . .
H21 H 0.2792 0.7431 0.1170 0.027 Uiso 1 1 calc R U . . .
O8 O 0.03367(7) 0.52918(18) 0.10785(10) 0.0279(4) Uani 1 1 d . . . . .
O9 O 0.21679(7) 1.06907(18) -0.01363(10) 0.0282(4) Uani 1 1 d . . . . .
O10 O 0.12301(7) 1.06011(18) -0.04874(10) 0.0291(4) Uani 1 1 d . . . . .
O11 O 0.41683(7) 0.53958(19) 0.24892(10) 0.0298(4) Uani 1 1 d . . . . .
O5 O 0.08878(7) 0.88183(19) -0.02313(11) 0.0322(4) Uani 1 1 d . . . . .
O12 O 0.38487(7) 0.35546(18) 0.28971(10) 0.0312(4) Uani 1 1 d . . . . .
O6 O 0.27821(7) 0.90278(19) 0.05225(11) 0.0316(4) Uani 1 1 d . . . . .
C16 C 0.12724(10) 0.5256(3) 0.13474(13) 0.0235(5) Uani 1 1 d . . . . .
C17 C 0.31980(10) 0.5316(3) 0.20742(13) 0.0240(5) Uani 1 1 d . . . . .
C18 C 0.18830(10) 0.8840(3) 0.03483(13) 0.0236(5) Uani 1 1 d . . . . .
C19 C 0.16931(10) 0.5859(2) 0.12892(13) 0.0224(5) Uani 1 1 d . . . . .
C20 C 0.26587(10) 0.5904(2) 0.16586(13) 0.0220(5) Uani 1 1 d . . . . .
C21 C 0.07069(10) 0.5870(3) 0.09300(14) 0.0243(5) Uani 1 1 d . . . . .
C22 C 0.20007(9) 0.7640(3) 0.07888(13) 0.0229(5) Uani 1 1 d . . . . .
C23 C 0.13055(10) 0.9383(3) -0.01253(14) 0.0259(5) Uani 1 1 d . . . . .
C24 C 0.36407(10) 0.5936(3) 0.20094(13) 0.0249(5) Uani 1 1 d . . . . .
C25 C 0.13850(10) 0.3980(3) 0.17815(14) 0.0261(5) Uani 1 1 d . . . . .
C26 C 0.23146(10) 0.9489(3) 0.02759(13) 0.0251(5) Uani 1 1 d . . . . .
C27 C 0.00505(11) 0.3543(3) 0.15961(16) 0.0320(6) Uani 1 1 d . . . . .
H1 H -0.0234 0.4134 0.1580 0.048 Uiso 1 1 calc R U . . .
H2 H 0.0181 0.2864 0.2035 0.048 Uiso 1 1 calc R U . . .
H3 H -0.0121 0.3085 0.1061 0.048 Uiso 1 1 calc R U . . .
C28 C 0.33088(10) 0.4042(3) 0.25069(14) 0.0273(5) Uani 1 1 d . . . . .
C29 C 0.05499(11) 0.4384(3) 0.17698(15) 0.0276(5) Uani 1 1 d . . . . .
C30 C 0.15337(11) 1.2510(3) -0.08455(17) 0.0349(6) Uani 1 1 d . . . . .
H4 H 0.1403 1.2064 -0.1373 0.052 Uiso 1 1 calc R U . . .
H5 H 0.1857 1.3106 -0.0688 0.052 Uiso 1 1 calc R U . . .
H6 H 0.1222 1.3050 -0.0906 0.052 Uiso 1 1 calc R U . . .
C31 C 0.17160(10) 1.1457(3) -0.01883(15) 0.0290(6) Uani 1 1 d . . . . .
C32 C 0.48194(11) 0.3733(3) 0.33816(19) 0.0421(7) Uani 1 1 d . . . . .
H7 H 0.4926 0.3106 0.3837 0.063 Uiso 1 1 calc R U . . .
H8 H 0.5136 0.4356 0.3550 0.063 Uiso 1 1 calc R U . . .
H9 H 0.4733 0.3216 0.2894 0.063 Uiso 1 1 calc R U . . .
C33 C 0.08411(12) 0.5174(3) 0.25723(16) 0.0341(6) Uani 1 1 d . . . . .
H10 H 0.1144 0.5737 0.2623 0.051 Uiso 1 1 calc R U . . .
H11 H 0.1006 0.4540 0.3040 0.051 Uiso 1 1 calc R U . . .
H12 H 0.0562 0.5756 0.2575 0.051 Uiso 1 1 calc R U . . .
C34 C 0.43801(11) 0.5345(3) 0.38826(15) 0.0353(6) Uani 1 1 d . . . . .
H13 H 0.4030 0.5856 0.3694 0.053 Uiso 1 1 calc R U . . .
H14 H 0.4698 0.5979 0.4084 0.053 Uiso 1 1 calc R U . . .
H15 H 0.4461 0.4731 0.4332 0.053 Uiso 1 1 calc R U . . .
C35 C 0.43028(10) 0.4531(3) 0.31717(15) 0.0325(6) Uani 1 1 d . . . . .
C36 C 0.19191(13) 1.2056(3) 0.06531(16) 0.0394(7) Uani 1 1 d . . . . .
H16 H 0.1608 1.2568 0.0612 0.059 Uiso 1 1 calc R U . . .
H17 H 0.2242 1.2665 0.0832 0.059 Uiso 1 1 calc R U . . .
H18 H 0.2039 1.1323 0.1058 0.059 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
N1 C19 1.353(3) . ?
N1 C22 1.365(3) . ?
O1 C24 1.215(3) . ?
O2 C25 1.218(3) . ?
O7 C25 1.353(3) . ?
O7 C29 1.438(3) . ?
O3 C21 1.210(3) . ?
O4 C28 1.218(3) . ?
N2 C19 1.364(3) . ?
N2 C20 1.369(3) . ?
N3 C20 1.350(3) . ?
N3 C22 1.361(3) . ?
O8 C21 1.360(3) . ?
O8 C29 1.438(3) . ?
O9 C26 1.358(3) . ?
O9 C31 1.441(3) . ?
O10 C23 1.347(3) . ?
O10 C31 1.430(3) . ?
O11 C24 1.351(3) . ?
O11 C35 1.439(3) . ?
O5 C23 1.216(3) . ?
O12 C28 1.358(3) . ?
O12 C35 1.447(3) . ?
O6 C26 1.216(3) . ?
C16 C19 1.393(3) . ?
C16 C25 1.447(4) . ?
C16 C21 1.460(3) . ?
C17 C20 1.392(3) . ?
C17 C28 1.444(4) . ?
C17 C24 1.464(3) . ?
C18 C22 1.387(4) . ?
C18 C23 1.456(3) . ?
C18 C26 1.456(3) . ?
C27 C29 1.506(4) . ?
C29 C33 1.511(4) . ?
C30 C31 1.497(4) . ?
C31 C36 1.520(4) . ?
C32 C35 1.502(4) . ?
C34 C35 1.507(4) . ?

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
C19 N1 C22 123.7(2) . . ?
C25 O7 C29 117.65(19) . . ?
C19 N2 C20 123.5(2) . . ?
C20 N3 C22 123.88(19) . . ?
C21 O8 C29 119.43(19) . . ?
C26 O9 C31 117.55(17) . . ?
C23 O10 C31 118.57(19) . . ?
C24 O11 C35 119.27(18) . . ?
C28 O12 C35 117.4(2) . . ?
C19 C16 C25 120.0(2) . . ?
C19 C16 C21 120.0(2) . . ?
C25 C16 C21 119.9(2) . . ?
C20 C17 C28 120.6(2) . . ?
C20 C17 C24 119.4(2) . . ?
C28 C17 C24 119.8(2) . . ?
C22 C18 C23 120.0(2) . . ?
C22 C18 C26 120.7(2) . . ?
C23 C18 C26 119.0(2) . . ?
N1 C19 N2 116.2(2) . . ?
N1 C19 C16 122.2(2) . . ?
N2 C19 C16 121.6(2) . . ?
N3 C20 N2 116.3(2) . . ?
N3 C20 C17 122.7(2) . . ?
N2 C20 C17 121.0(2) . . ?
O3 C21 O8 118.0(2) . . ?
O3 C21 C16 125.5(2) . . ?
O8 C21 C16 116.4(2) . . ?
N3 C22 N1 116.2(2) . . ?
N3 C22 C18 122.4(2) . . ?
N1 C22 C18 121.4(2) . . ?
O5 C23 O10 117.7(2) . . ?
O5 C23 C18 125.5(2) . . ?
O10 C23 C18 116.8(2) . . ?
O1 C24 O11 118.2(2) . . ?
O1 C24 C17 125.3(2) . . ?
O11 C24 C17 116.5(2) . . ?
O2 C25 O7 117.6(2) . . ?
O2 C25 C16 125.9(2) . . ?
O7 C25 C16 116.3(2) . . ?
O6 C26 O9 117.6(2) . . ?
O6 C26 C18 125.9(2) . . ?
O9 C26 C18 116.4(2) . . ?
O4 C28 O12 117.4(2) . . ?
O4 C28 C17 126.3(2) . . ?
O12 C28 C17 116.2(2) . . ?
O7 C29 O8 109.91(17) . . ?
O7 C29 C27 106.4(2) . . ?
O8 C29 C27 106.5(2) . . ?
O7 C29 C33 109.1(2) . . ?
O8 C29 C33 110.4(2) . . ?
C27 C29 C33 114.4(2) . . ?
O10 C31 O9 109.6(2) . . ?
O10 C31 C30 105.60(19) . . ?
O9 C31 C30 106.78(19) . . ?
O10 C31 C36 111.3(2) . . ?
O9 C31 C36 110.2(2) . . ?
C30 C31 C36 113.2(2) . . ?
O11 C35 O12 109.41(18) . . ?
O11 C35 C32 105.8(2) . . ?
O12 C35 C32 106.4(2) . . ?
O11 C35 C34 111.2(2) . . ?
O12 C35 C34 109.5(2) . . ?
C32 C35 C34 114.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 N1 C19 N2 -4.2(3) . . . . ?
C22 N1 C19 C16 176.6(2) . . . . ?
C20 N2 C19 N1 1.8(3) . . . . ?
C20 N2 C19 C16 -179.0(2) . . . . ?
C25 C16 C19 N1 173.9(2) . . . . ?
C21 C16 C19 N1 -2.6(3) . . . . ?
C25 C16 C19 N2 -5.3(3) . . . . ?
C21 C16 C19 N2 178.27(19) . . . . ?
C22 N3 C20 N2 0.4(3) . . . . ?
C22 N3 C20 C17 179.8(2) . . . . ?
C19 N2 C20 N3 0.0(3) . . . . ?
C19 N2 C20 C17 -179.5(2) . . . . ?
C28 C17 C20 N3 -175.7(2) . . . . ?
C24 C17 C20 N3 -1.1(3) . . . . ?
C28 C17 C20 N2 3.8(3) . . . . ?
C24 C17 C20 N2 178.4(2) . . . . ?
C29 O8 C21 O3 -166.0(2) . . . . ?
C29 O8 C21 C16 15.8(3) . . . . ?
C19 C16 C21 O3 7.8(4) . . . . ?
C25 C16 C21 O3 -168.7(2) . . . . ?
C19 C16 C21 O8 -174.17(19) . . . . ?
C25 C16 C21 O8 9.3(3) . . . . ?
C20 N3 C22 N1 -2.5(3) . . . . ?
C20 N3 C22 C18 177.8(2) . . . . ?
C19 N1 C22 N3 4.5(3) . . . . ?
C19 N1 C22 C18 -175.8(2) . . . . ?
C23 C18 C22 N3 176.1(2) . . . . ?
C26 C18 C22 N3 3.1(3) . . . . ?
C23 C18 C22 N1 -3.6(3) . . . . ?
C26 C18 C22 N1 -176.7(2) . . . . ?
C31 O10 C23 O5 161.9(2) . . . . ?
C31 O10 C23 C18 -19.3(3) . . . . ?
C22 C18 C23 O5 -6.2(4) . . . . ?
C26 C18 C23 O5 167.0(2) . . . . ?
C22 C18 C23 O10 175.2(2) . . . . ?
C26 C18 C23 O10 -11.6(3) . . . . ?
C35 O11 C24 O1 166.7(2) . . . . ?
C35 O11 C24 C17 -16.2(3) . . . . ?
C20 C17 C24 O1 -9.3(4) . . . . ?
C28 C17 C24 O1 165.3(2) . . . . ?
C20 C17 C24 O11 173.8(2) . . . . ?
C28 C17 C24 O11 -11.5(3) . . . . ?
C29 O7 C25 O2 154.7(2) . . . . ?
C29 O7 C25 C16 -29.3(3) . . . . ?
C19 C16 C25 O2 -3.3(4) . . . . ?
C21 C16 C25 O2 173.2(2) . . . . ?
C19 C16 C25 O7 -179.0(2) . . . . ?
C21 C16 C25 O7 -2.5(3) . . . . ?
C31 O9 C26 O6 -159.9(2) . . . . ?
C31 O9 C26 C18 22.7(3) . . . . ?
C22 C18 C26 O6 5.7(4) . . . . ?
C23 C18 C26 O6 -167.4(2) . . . . ?
C22 C18 C26 O9 -177.2(2) . . . . ?
C23 C18 C26 O9 9.7(3) . . . . ?
C35 O12 C28 O4 -156.5(2) . . . . ?
C35 O12 C28 C17 27.3(3) . . . . ?
C20 C17 C28 O4 4.4(4) . . . . ?
C24 C17 C28 O4 -170.2(2) . . . . ?
C20 C17 C28 O12 -179.7(2) . . . . ?
C24 C17 C28 O12 5.7(3) . . . . ?
C25 O7 C29 O8 52.1(3) . . . . ?
C25 O7 C29 C27 167.03(18) . . . . ?
C25 O7 C29 C33 -69.0(2) . . . . ?
C21 O8 C29 O7 -44.9(3) . . . . ?
C21 O8 C29 C27 -159.7(2) . . . . ?
C21 O8 C29 C33 75.5(3) . . . . ?
C23 O10 C31 O9 49.6(3) . . . . ?
C23 O10 C31 C30 164.3(2) . . . . ?
C23 O10 C31 C36 -72.5(3) . . . . ?
C26 O9 C31 O10 -51.3(2) . . . . ?
C26 O9 C31 C30 -165.2(2) . . . . ?
C26 O9 C31 C36 71.5(3) . . . . ?
C24 O11 C35 O12 46.5(3) . . . . ?
C24 O11 C35 C32 160.8(2) . . . . ?
C24 O11 C35 C34 -74.5(3) . . . . ?
C28 O12 C35 O11 -52.4(3) . . . . ?
C28 O12 C35 C32 -166.3(2) . . . . ?
C28 O12 C35 C34 69.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H19 O3 0.88 1.97 2.649(3) 132.9 .
N1 H19 O5 0.88 1.94 2.623(3) 133.4 .
N2 H20 O2 0.88 1.96 2.635(3) 132.5 .
N2 H20 O4 0.88 1.97 2.644(3) 132.8 .
N3 H21 O1 0.88 1.97 2.643(3) 132.5 .
N3 H21 O6 0.88 2.01 2.680(3) 132.3 .
C27 H3 O3 0.98 2.49 3.374(3) 150.0 5_565
C27 H3 O5 0.98 2.63 3.408(3) 136.7 5_565
C30 H5 O9 0.98 2.58 3.527(3) 163.2 7_575
C32 H8 O10 0.98 2.57 3.374(3) 139.3 8_566
C34 H15 O5 0.98 2.61 3.464(3) 145.7 4_545
N1 H19 O3 0.88 1.97 2.649(3) 132.9 .
N1 H19 O5 0.88 1.94 2.623(3) 133.4 .

_refine_diff_density_max         0.562
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_91220su
_database_code_depnum_ccdc_archive 'CCDC 2014518'
loop_
_audit_author_name
_audit_author_address
'Takayuki Tanaka'
;Kyoto University
Japan
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3.5 H3.5 N0.5 O1, C0.17 H0.67 O0.17 '
_chemical_formula_sum            'C3.67 H4.17 N0.50 O1.17'
_chemical_formula_weight         73.91

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

_space_group_crystal_system      hexagonal
_space_group_IT_number           176
_space_group_name_H-M_alt        'P 63/m'
_space_group_name_Hall           '-P 6c'

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

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

_cell_length_a                   13.202(7)
_cell_length_b                   13.202(7)
_cell_length_c                   6.454(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     974.2(12)
_cell_formula_units_Z            12
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    628
_cell_measurement_theta_min      31.5
_cell_measurement_theta_max      72.9

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.953
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            26405
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0743
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.866
_diffrn_reflns_theta_max         73.194
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             707
_reflns_number_gt                581
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.4910P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         707
_refine_ls_number_parameters     105
_refine_ls_number_restraints     87
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1171
_refine_ls_wR_factor_gt          0.1146
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.08840(14) 0.11049(14) 0.2500 0.0325(5) Uani 1 2 d S T P . .
H1 H 0.1466 0.1832 0.2500 0.039 Uiso 1 2 calc R U P . .
C7 C 0.11518(17) 0.02309(16) 0.2500 0.0323(5) Uani 1 2 d S T P . .
O3 O 0.17674(14) -0.15425(14) 0.2500 0.0490(5) Uani 1 2 d S T P A .
C8 C 0.23086(18) 0.04627(19) 0.2500 0.0372(5) Uani 1 2 d S T P A .
O4 O 0.31244(13) 0.25202(13) 0.2500 0.0472(5) Uani 1 2 d S T P A .
C11 C 0.2547(2) -0.0509(2) 0.2500 0.0456(6) Uani 1 2 d DS T P . .
C9 C 0.32762(19) 0.1673(2) 0.2500 0.0435(6) Uani 1 2 d DS T P . .
C12A C 0.3864(11) -0.0072(11) 0.225(3) 0.048(3) Uani 0.25 1 d D U P A -1
H6 H 0.4005 -0.0728 0.2540 0.058 Uiso 0.25 1 calc R U P A -1
H7 H 0.4094 0.0175 0.0799 0.058 Uiso 0.25 1 calc R U P A -1
C10A C 0.4492(13) 0.1835(16) 0.248(6) 0.052(2) Uani 0.25 1 d D U P A -1
H8 H 0.4717 0.1816 0.1021 0.062 Uiso 0.25 1 calc R U P A -1
H9 H 0.5043 0.2621 0.3037 0.062 Uiso 0.25 1 calc R U P A -1
C13 C 0.4635(18) 0.0947(14) 0.368(2) 0.049(3) Uani 0.25 1 d D U P A -1
H2 H 0.4319 0.0838 0.5108 0.059 Uiso 0.25 1 calc R U P A -1
H3 H 0.5456 0.1117 0.3721 0.059 Uiso 0.25 1 calc R U P A -1
O5 O 0.4440(7) -0.2257(9) 0.1848(16) 0.087(4) Uani 0.1667 1 d D U P B -1
H14 H 0.5001 -0.2384 0.1752 0.131 Uiso 0.1667 1 calc R U P B -1
C14 C 0.342(2) -0.329(3) 0.267(10) 0.076(7) Uani 0.1667 1 d D U P B -1
H15 H 0.3537 -0.3964 0.2544 0.113 Uiso 0.1667 1 calc R U P B -1
H16 H 0.2727 -0.3434 0.1888 0.113 Uiso 0.1667 1 calc R U P B -1
H17 H 0.3322 -0.3160 0.4133 0.113 Uiso 0.1667 1 calc R U P B -1
C12B C 0.3746(11) -0.0355(11) 0.276(3) 0.048(3) Uani 0.25 1 d D U P A -2
H10 H 0.3797 -0.0995 0.2056 0.058 Uiso 0.25 1 calc R U P A -2
H11 H 0.3930 -0.0356 0.4245 0.058 Uiso 0.25 1 calc R U P A -2
C10B C 0.4530(13) 0.1948(17) 0.207(3) 0.052(2) Uani 0.25 1 d D U P A -2
H12 H 0.5041 0.2403 0.3236 0.062 Uiso 0.25 1 calc R U P A -2
H13 H 0.4825 0.2433 0.0800 0.062 Uiso 0.25 1 calc R U P A -2
C15 C 0.4586(17) 0.0818(13) 0.177(2) 0.046(3) Uani 0.25 1 d D U P A -2
H4 H 0.4547 0.0677 0.0262 0.055 Uiso 0.25 1 calc R U P A -2
H5 H 0.5380 0.1006 0.2217 0.055 Uiso 0.25 1 calc R U P A -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C7 1.365(3) . ?
N2 C7 1.367(3) 3 ?
N2 H1 0.8800 . ?
C7 N2 1.367(3) 4 ?
C7 C8 1.400(3) . ?
O3 C11 1.232(3) . ?
C8 C9 1.464(3) . ?
C8 C11 1.465(3) . ?
O4 C9 1.231(3) . ?
C11 C12B 1.501(13) . ?
C11 C12A 1.543(13) . ?
C9 C10A 1.510(14) . ?
C9 C10B 1.533(14) . ?
C12A C13 1.526(15) . ?
C12A H6 0.9900 . ?
C12A H7 0.9900 . ?
C10A C13 1.497(19) . ?
C10A H8 0.9900 . ?
C10A H9 0.9900 . ?
C13 H2 0.9900 . ?
C13 H3 0.9900 . ?
O5 C14 1.451(11) . ?
O5 H14 0.8400 . ?
C14 H15 0.9800 . ?
C14 H16 0.9800 . ?
C14 H17 0.9800 . ?
C12B C15 1.521(14) . ?
C12B H10 0.9900 . ?
C12B H11 0.9900 . ?
C10B C15 1.542(17) . ?
C10B H12 0.9900 . ?
C10B H13 0.9900 . ?
C15 H4 0.9900 . ?
C15 H5 0.9900 . ?

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 N2 C7 124.10(19) . 3 ?
C7 N2 H1 117.9 . . ?
C7 N2 H1 117.9 3 . ?
N2 C7 N2 115.90(19) . 4 ?
N2 C7 C8 122.04(17) . . ?
N2 C7 C8 122.06(17) 4 . ?
C7 C8 C9 119.99(19) . . ?
C7 C8 C11 119.79(19) . . ?
C9 C8 C11 120.22(19) . . ?
O3 C11 C8 122.97(19) . . ?
O3 C11 C12B 112.9(5) . . ?
C8 C11 C12B 123.7(5) . . ?
O3 C11 C12A 125.1(5) . . ?
C8 C11 C12A 111.6(6) . . ?
O4 C9 C8 122.82(19) . . ?
O4 C9 C10A 121.0(7) . . ?
C8 C9 C10A 116.1(7) . . ?
O4 C9 C10B 115.6(7) . . ?
C8 C9 C10B 120.5(7) . . ?
C13 C12A C11 113.4(14) . . ?
C13 C12A H6 108.9 . . ?
C11 C12A H6 108.9 . . ?
C13 C12A H7 108.9 . . ?
C11 C12A H7 108.9 . . ?
H6 C12A H7 107.7 . . ?
C13 C10A C9 115.2(19) . . ?
C13 C10A H8 108.5 . . ?
C9 C10A H8 108.5 . . ?
C13 C10A H9 108.5 . . ?
C9 C10A H9 108.5 . . ?
H8 C10A H9 107.5 . . ?
C10A C13 C12A 94.9(15) . . ?
C10A C13 H2 112.8 . . ?
C12A C13 H2 112.8 . . ?
C10A C13 H3 112.8 . . ?
C12A C13 H3 112.8 . . ?
H2 C13 H3 110.2 . . ?
C14 O5 H14 109.5 . . ?
O5 C14 H15 109.5 . . ?
O5 C14 H16 109.5 . . ?
H15 C14 H16 109.5 . . ?
O5 C14 H17 109.5 . . ?
H15 C14 H17 109.5 . . ?
H16 C14 H17 109.5 . . ?
C11 C12B C15 105.9(13) . . ?
C11 C12B H10 110.5 . . ?
C15 C12B H10 110.5 . . ?
C11 C12B H11 110.5 . . ?
C15 C12B H11 110.5 . . ?
H10 C12B H11 108.7 . . ?
C9 C10B C15 111.2(14) . . ?
C9 C10B H12 109.4 . . ?
C15 C10B H12 109.4 . . ?
C9 C10B H13 109.4 . . ?
C15 C10B H13 109.4 . . ?
H12 C10B H13 108.0 . . ?
C12B C15 C10B 124.8(15) . . ?
C12B C15 H4 106.1 . . ?
C10B C15 H4 106.1 . . ?
C12B C15 H5 106.1 . . ?
C10B C15 H5 106.1 . . ?
H4 C15 H5 106.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 C7 N2 0.0 3 . . 4 ?
C7 N2 C7 C8 180.0 3 . . . ?
N2 C7 C8 C9 0.0 . . . . ?
N2 C7 C8 C9 180.0 4 . . . ?
N2 C7 C8 C11 180.0 . . . . ?
N2 C7 C8 C11 0.0 4 . . . ?
C7 C8 C11 O3 0.0 . . . . ?
C9 C8 C11 O3 180.0 . . . . ?
C7 C8 C11 C12B -172.3(10) . . . . ?
C9 C8 C11 C12B 7.7(10) . . . . ?
C7 C8 C11 C12A 173.6(9) . . . . ?
C9 C8 C11 C12A -6.4(9) . . . . ?
C7 C8 C9 O4 0.0 . . . . ?
C11 C8 C9 O4 180.0 . . . . ?
C7 C8 C9 C10A -179.4(18) . . . . ?
C11 C8 C9 C10A 0.6(18) . . . . ?
C7 C8 C9 C10B -167.8(8) . . . . ?
C11 C8 C9 C10B 12.2(8) . . . . ?
O3 C11 C12A C13 -139.1(10) . . . . ?
C8 C11 C12A C13 47.4(16) . . . . ?
O4 C9 C10A C13 144.9(14) . . . . ?
C8 C9 C10A C13 -36(3) . . . . ?
C9 C10A C13 C12A 67(3) . . . . ?
C11 C12A C13 C10A -74.3(19) . . . . ?
O3 C11 C12B C15 154.8(8) . . . . ?
C8 C11 C12B C15 -32.2(15) . . . . ?
O4 C9 C10B C15 -171.4(11) . . . . ?
C8 C9 C10B C15 -2.8(18) . . . . ?
C11 C12B C15 C10B 44(2) . . . . ?
C9 C10B C15 C12B -28(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H1 O3 0.88 1.90 2.588(3) 133.6 3
N2 H1 O4 0.88 1.91 2.591(3) 133.5 .

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_91218su
_database_code_depnum_ccdc_archive 'CCDC 2014519'
loop_
_audit_author_name
_audit_author_address
'Takayuki Tanaka'
;Kyoto University
Japan
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H33 N3 O6, C H2 Cl2'
_chemical_formula_sum            'C28 H35 Cl2 N3 O6'
_chemical_formula_weight         580.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.2710(11)
_cell_length_b                   11.3037(2)
_cell_length_c                   12.5205(8)
_cell_angle_alpha                73.166(14)
_cell_angle_beta                 87.132(18)
_cell_angle_gamma                65.188(16)
_cell_volume                     1381.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1365
_cell_measurement_theta_min      30.8
_cell_measurement_theta_max      72.9

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   0.648
_exptl_transmission_factor_max   0.904
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    2.514
_shelx_estimated_absorpt_T_min   0.584
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            17867
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.701
_diffrn_reflns_theta_max         65.998
_diffrn_reflns_theta_full        65.998
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             4675
_reflns_number_gt                4249
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1133P)²+0.8157P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4675
_refine_ls_number_parameters     358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1694
_refine_ls_wR_factor_gt          0.1671
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.23791(19) 0.0358(2) 0.58138(17) 0.0137(4) Uani 1 1 d . . . . .
C2 C 0.19924(19) 0.1677(2) 0.60112(17) 0.0141(4) Uani 1 1 d . . . . .
C3 C 0.2695(2) 0.1765(2) 0.69559(18) 0.0182(5) Uani 1 1 d . . . . .
H1 H 0.2171 0.1728 0.7613 0.022 Uiso 1 1 calc R U . . .
H2 H 0.2729 0.2664 0.6731 0.022 Uiso 1 1 calc R U . . .
C4 C 0.4091(2) 0.0656(2) 0.73155(17) 0.0169(5) Uani 1 1 d . . . . .
C5 C 0.4022(2) -0.0713(2) 0.75314(17) 0.0169(5) Uani 1 1 d . . . . .
H3 H 0.4923 -0.1449 0.7722 0.020 Uiso 1 1 calc R U . . .
H4 H 0.3517 -0.0845 0.8190 0.020 Uiso 1 1 calc R U . . .
C6 C 0.34058(19) -0.0861(2) 0.65675(17) 0.0144(4) Uani 1 1 d . . . . .
C7 C 0.5015(2) 0.0823(3) 0.6409(2) 0.0246(5) Uani 1 1 d . . . . .
H13 H 0.5900 0.0097 0.6656 0.037 Uiso 1 1 calc R U . . .
H14 H 0.5035 0.1713 0.6272 0.037 Uiso 1 1 calc R U . . .
H15 H 0.4704 0.0767 0.5716 0.037 Uiso 1 1 calc R U . . .
C8 C 0.4581(2) 0.0735(2) 0.8396(2) 0.0250(5) Uani 1 1 d . . . . .
H16 H 0.5479 0.0031 0.8624 0.038 Uiso 1 1 calc R U . . .
H17 H 0.4009 0.0590 0.8987 0.038 Uiso 1 1 calc R U . . .
H18 H 0.4570 0.1637 0.8271 0.038 Uiso 1 1 calc R U . . .
C9 C 0.1704(2) -0.2408(2) 0.38185(17) 0.0134(4) Uani 1 1 d . . . . .
C10 C 0.2693(2) -0.3653(2) 0.46003(16) 0.0153(4) Uani 1 1 d . . . . .
C11 C 0.2877(2) -0.5018(2) 0.45010(17) 0.0173(5) Uani 1 1 d . . . . .
H5 H 0.2250 -0.5307 0.4959 0.021 Uiso 1 1 calc R U . . .
H6 H 0.3774 -0.5701 0.4813 0.021 Uiso 1 1 calc R U . . .
C12 C 0.2678(2) -0.5012(2) 0.32978(17) 0.0144(4) Uani 1 1 d . . . . .
C13 C 0.1293(2) -0.3924(2) 0.28467(18) 0.0165(5) Uani 1 1 d . . . . .
H7 H 0.1160 -0.3849 0.2050 0.020 Uiso 1 1 calc R U . . .
H8 H 0.0654 -0.4233 0.3260 0.020 Uiso 1 1 calc R U . . .
C14 C 0.10014(19) -0.2528(2) 0.29333(16) 0.0136(4) Uani 1 1 d . . . . .
C15 C 0.3718(2) -0.4702(2) 0.25985(18) 0.0197(5) Uani 1 1 d . . . . .
H19 H 0.3541 -0.4624 0.1817 0.030 Uiso 1 1 calc R U . . .
H20 H 0.4586 -0.5442 0.2886 0.030 Uiso 1 1 calc R U . . .
H21 H 0.3694 -0.3841 0.2643 0.030 Uiso 1 1 calc R U . . .
C16 C 0.2779(2) -0.6403(2) 0.32873(18) 0.0192(5) Uani 1 1 d . . . . .
H22 H 0.2089 -0.6588 0.3710 0.029 Uiso 1 1 calc R U . . .
H23 H 0.3639 -0.7115 0.3633 0.029 Uiso 1 1 calc R U . . .
H24 H 0.2674 -0.6395 0.2513 0.029 Uiso 1 1 calc R U . . .
C17 C -0.09137(19) 0.2453(2) 0.26952(16) 0.0128(4) Uani 1 1 d . . . . .
C18 C -0.16319(19) 0.2325(2) 0.18262(17) 0.0141(4) Uani 1 1 d . . . . .
C19 C -0.2792(2) 0.3571(2) 0.11563(18) 0.0180(5) Uani 1 1 d . . . . .
H9 H -0.3591 0.3627 0.1546 0.022 Uiso 1 1 calc R U . . .
H10 H -0.2905 0.3460 0.0417 0.022 Uiso 1 1 calc R U . . .
C20 C -0.26699(19) 0.4912(2) 0.09729(17) 0.0142(4) Uani 1 1 d . . . . .
C21 C -0.2434(2) 0.5010(2) 0.21266(18) 0.0188(5) Uani 1 1 d . . . . .
H11 H -0.2297 0.5844 0.2029 0.023 Uiso 1 1 calc R U . . .
H12 H -0.3233 0.5114 0.2530 0.023 Uiso 1 1 calc R U . . .
C22 C -0.1272(2) 0.3795(2) 0.28479(17) 0.0158(4) Uani 1 1 d . . . . .
C23 C -0.1534(2) 0.4927(2) 0.02651(19) 0.0237(5) Uani 1 1 d . . . . .
H25 H -0.1453 0.5781 0.0171 0.036 Uiso 1 1 calc R U . . .
H26 H -0.1699 0.4857 -0.0470 0.036 Uiso 1 1 calc R U . . .
H27 H -0.0719 0.4153 0.0640 0.036 Uiso 1 1 calc R U . . .
C24 C -0.3945(2) 0.6114(2) 0.03782(18) 0.0191(5) Uani 1 1 d . . . . .
H28 H -0.4676 0.6113 0.0836 0.029 Uiso 1 1 calc R U . . .
H29 H -0.4110 0.6028 -0.0351 0.029 Uiso 1 1 calc R U . . .
H30 H -0.3865 0.6972 0.0268 0.029 Uiso 1 1 calc R U . . .
C25 C 0.17418(19) 0.0245(2) 0.49424(16) 0.0121(4) Uani 1 1 d . . . . .
C26 C 0.14162(19) -0.1137(2) 0.39421(16) 0.0123(4) Uani 1 1 d . . . . .
C27 C 0.01040(19) 0.1292(2) 0.33862(16) 0.0121(4) Uani 1 1 d . . . . .
N1 N 0.20451(16) -0.09777(17) 0.47628(14) 0.0125(4) Uani 1 1 d . . . . .
H31 H 0.2681 -0.1707 0.5199 0.015 Uiso 1 1 calc R U . . .
N2 N 0.04650(16) 0.00316(17) 0.32640(14) 0.0123(4) Uani 1 1 d . . . . .
H32 H 0.0061 -0.0035 0.2715 0.015 Uiso 1 1 calc R U . . .
N3 N 0.07677(16) 0.13586(17) 0.42326(14) 0.0124(4) Uani 1 1 d . . . . .
H33 H 0.0557 0.2162 0.4327 0.015 Uiso 1 1 calc R U . . .
O1 O 0.10863(14) 0.27311(15) 0.54385(12) 0.0180(3) Uani 1 1 d . . . . .
O2 O 0.37673(14) -0.20034(15) 0.64482(12) 0.0197(4) Uani 1 1 d . . . . .
O3 O 0.33485(15) -0.36094(15) 0.53284(12) 0.0213(4) Uani 1 1 d . . . . .
O4 O 0.01599(14) -0.15238(15) 0.22577(12) 0.0168(3) Uani 1 1 d . . . . .
O5 O -0.13440(14) 0.12346(14) 0.16315(12) 0.0179(3) Uani 1 1 d . . . . .
O6 O -0.06860(15) 0.39734(15) 0.35437(13) 0.0216(4) Uani 1 1 d . . . . .
C28 C -0.1384(2) 0.9757(3) -0.0262(2) 0.0297(6) Uani 1 1 d . . . . .
H34 H -0.0616 0.9839 -0.0637 0.036 Uiso 1 1 calc R U . . .
H35 H -0.1204 0.9553 0.0553 0.036 Uiso 1 1 calc R U . . .
Cl1 Cl -0.27768(6) 1.13124(6) -0.07525(5) 0.0345(2) Uani 1 1 d . . . . .
Cl2 Cl -0.16018(7) 0.84111(7) -0.05179(8) 0.0533(3) Uani 1 1 d . . . . .


_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
C1 C25 1.400(3) . ?
C1 C2 1.460(3) . ?
C1 C6 1.465(3) . ?
C2 O1 1.238(3) . ?
C2 C3 1.505(3) . ?
C3 C4 1.529(3) . ?
C3 H1 0.9900 . ?
C3 H2 0.9900 . ?
C4 C5 1.526(3) . ?
C4 C8 1.527(3) . ?
C4 C7 1.527(3) . ?
C5 C6 1.505(3) . ?
C5 H3 0.9900 . ?
C5 H4 0.9900 . ?
C6 O2 1.232(3) . ?
C7 H13 0.9800 . ?
C7 H14 0.9800 . ?
C7 H15 0.9800 . ?
C8 H16 0.9800 . ?
C8 H17 0.9800 . ?
C8 H18 0.9800 . ?
C9 C26 1.387(3) . ?
C9 C14 1.463(3) . ?
C9 C10 1.475(3) . ?
C10 O3 1.226(3) . ?
C10 C11 1.510(3) . ?
C11 C12 1.532(3) . ?
C11 H5 0.9900 . ?
C11 H6 0.9900 . ?
C12 C15 1.525(3) . ?
C12 C13 1.531(3) . ?
C12 C16 1.532(3) . ?
C13 C14 1.506(3) . ?
C13 H7 0.9900 . ?
C13 H8 0.9900 . ?
C14 O4 1.235(3) . ?
C15 H19 0.9800 . ?
C15 H20 0.9800 . ?
C15 H21 0.9800 . ?
C16 H22 0.9800 . ?
C16 H23 0.9800 . ?
C16 H24 0.9800 . ?
C17 C27 1.402(3) . ?
C17 C18 1.462(3) . ?
C17 C22 1.466(3) . ?
C18 O5 1.231(3) . ?
C18 C19 1.509(3) . ?
C19 C20 1.529(3) . ?
C19 H9 0.9900 . ?
C19 H10 0.9900 . ?
C20 C23 1.523(3) . ?
C20 C21 1.525(3) . ?
C20 C24 1.533(3) . ?
C21 C22 1.519(3) . ?
C21 H11 0.9900 . ?
C21 H12 0.9900 . ?
C22 O6 1.227(3) . ?
C23 H25 0.9800 . ?
C23 H26 0.9800 . ?
C23 H27 0.9800 . ?
C24 H28 0.9800 . ?
C24 H29 0.9800 . ?
C24 H30 0.9800 . ?
C25 N1 1.361(3) . ?
C25 N3 1.367(3) . ?
C26 N2 1.367(3) . ?
C26 N1 1.370(3) . ?
C27 N2 1.361(3) . ?
C27 N3 1.364(3) . ?
N1 H31 0.8800 . ?
N2 H32 0.8800 . ?
N3 H33 0.8800 . ?
C28 Cl2 1.755(3) . ?
C28 Cl1 1.757(3) . ?
C28 H34 0.9900 . ?
C28 H35 0.9900 . ?

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 C1 C2 120.54(18) . . ?
C25 C1 C6 120.09(19) . . ?
C2 C1 C6 119.32(18) . . ?
O1 C2 C1 122.29(18) . . ?
O1 C2 C3 118.42(19) . . ?
C1 C2 C3 119.28(18) . . ?
C2 C3 C4 115.70(18) . . ?
C2 C3 H1 108.4 . . ?
C4 C3 H1 108.4 . . ?
C2 C3 H2 108.4 . . ?
C4 C3 H2 108.4 . . ?
H1 C3 H2 107.4 . . ?
C5 C4 C8 109.44(17) . . ?
C5 C4 C7 110.63(19) . . ?
C8 C4 C7 109.46(18) . . ?
C5 C4 C3 106.89(16) . . ?
C8 C4 C3 109.34(18) . . ?
C7 C4 C3 111.03(18) . . ?
C6 C5 C4 114.89(17) . . ?
C6 C5 H3 108.5 . . ?
C4 C5 H3 108.5 . . ?
C6 C5 H4 108.5 . . ?
C4 C5 H4 108.5 . . ?
H3 C5 H4 107.5 . . ?
O2 C6 C1 122.29(19) . . ?
O2 C6 C5 119.03(18) . . ?
C1 C6 C5 118.67(19) . . ?
C4 C7 H13 109.5 . . ?
C4 C7 H14 109.5 . . ?
H13 C7 H14 109.5 . . ?
C4 C7 H15 109.5 . . ?
H13 C7 H15 109.5 . . ?
H14 C7 H15 109.5 . . ?
C4 C8 H16 109.5 . . ?
C4 C8 H17 109.5 . . ?
H16 C8 H17 109.5 . . ?
C4 C8 H18 109.5 . . ?
H16 C8 H18 109.5 . . ?
H17 C8 H18 109.5 . . ?
C26 C9 C14 120.31(18) . . ?
C26 C9 C10 120.26(18) . . ?
C14 C9 C10 119.41(18) . . ?
O3 C10 C9 122.18(19) . . ?
O3 C10 C11 119.58(18) . . ?
C9 C10 C11 118.23(17) . . ?
C10 C11 C12 113.82(16) . . ?
C10 C11 H5 108.8 . . ?
C12 C11 H5 108.8 . . ?
C10 C11 H6 108.8 . . ?
C12 C11 H6 108.8 . . ?
H5 C11 H6 107.7 . . ?
C15 C12 C13 111.69(16) . . ?
C15 C12 C11 109.95(17) . . ?
C13 C12 C11 106.75(17) . . ?
C15 C12 C16 109.26(17) . . ?
C13 C12 C16 109.01(16) . . ?
C11 C12 C16 110.15(16) . . ?
C14 C13 C12 114.90(17) . . ?
C14 C13 H7 108.5 . . ?
C12 C13 H7 108.5 . . ?
C14 C13 H8 108.5 . . ?
C12 C13 H8 108.5 . . ?
H7 C13 H8 107.5 . . ?
O4 C14 C9 122.32(19) . . ?
O4 C14 C13 118.43(18) . . ?
C9 C14 C13 119.25(17) . . ?
C12 C15 H19 109.5 . . ?
C12 C15 H20 109.5 . . ?
H19 C15 H20 109.5 . . ?
C12 C15 H21 109.5 . . ?
H19 C15 H21 109.5 . . ?
H20 C15 H21 109.5 . . ?
C12 C16 H22 109.5 . . ?
C12 C16 H23 109.5 . . ?
H22 C16 H23 109.5 . . ?
C12 C16 H24 109.5 . . ?
H22 C16 H24 109.5 . . ?
H23 C16 H24 109.5 . . ?
C27 C17 C18 119.99(19) . . ?
C27 C17 C22 120.25(18) . . ?
C18 C17 C22 119.76(17) . . ?
O5 C18 C17 122.66(18) . . ?
O5 C18 C19 118.48(18) . . ?
C17 C18 C19 118.84(18) . . ?
C18 C19 C20 114.18(16) . . ?
C18 C19 H9 108.7 . . ?
C20 C19 H9 108.7 . . ?
C18 C19 H10 108.7 . . ?
C20 C19 H10 108.7 . . ?
H9 C19 H10 107.6 . . ?
C23 C20 C21 110.59(17) . . ?
C23 C20 C19 110.34(18) . . ?
C21 C20 C19 107.02(17) . . ?
C23 C20 C24 109.33(16) . . ?
C21 C20 C24 109.77(17) . . ?
C19 C20 C24 109.76(16) . . ?
C22 C21 C20 114.73(18) . . ?
C22 C21 H11 108.6 . . ?
C20 C21 H11 108.6 . . ?
C22 C21 H12 108.6 . . ?
C20 C21 H12 108.6 . . ?
H11 C21 H12 107.6 . . ?
O6 C22 C17 122.80(18) . . ?
O6 C22 C21 118.82(19) . . ?
C17 C22 C21 118.38(18) . . ?
C20 C23 H25 109.5 . . ?
C20 C23 H26 109.5 . . ?
H25 C23 H26 109.5 . . ?
C20 C23 H27 109.5 . . ?
H25 C23 H27 109.5 . . ?
H26 C23 H27 109.5 . . ?
C20 C24 H28 109.5 . . ?
C20 C24 H29 109.5 . . ?
H28 C24 H29 109.5 . . ?
C20 C24 H30 109.5 . . ?
H28 C24 H30 109.5 . . ?
H29 C24 H30 109.5 . . ?
N1 C25 N3 116.39(17) . . ?
N1 C25 C1 121.97(18) . . ?
N3 C25 C1 121.64(19) . . ?
N2 C26 N1 115.91(18) . . ?
N2 C26 C9 121.81(18) . . ?
N1 C26 C9 122.26(18) . . ?
N2 C27 N3 116.34(17) . . ?
N2 C27 C17 121.75(18) . . ?
N3 C27 C17 121.90(19) . . ?
C25 N1 C26 123.75(17) . . ?
C25 N1 H31 118.1 . . ?
C26 N1 H31 118.1 . . ?
C27 N2 C26 123.97(17) . . ?
C27 N2 H32 118.0 . . ?
C26 N2 H32 118.0 . . ?
C27 N3 C25 123.61(18) . . ?
C27 N3 H33 118.2 . . ?
C25 N3 H33 118.2 . . ?
Cl2 C28 Cl1 111.52(14) . . ?
Cl2 C28 H34 109.3 . . ?
Cl1 C28 H34 109.3 . . ?
Cl2 C28 H35 109.3 . . ?
Cl1 C28 H35 109.3 . . ?
H34 C28 H35 108.0 . . ?

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
C25 C1 C2 O1 1.2(3) . . . . ?
C6 C1 C2 O1 -176.25(18) . . . . ?
C25 C1 C2 C3 179.92(18) . . . . ?
C6 C1 C2 C3 2.5(3) . . . . ?
O1 C2 C3 C4 -156.12(18) . . . . ?
C1 C2 C3 C4 25.1(3) . . . . ?
C2 C3 C4 C5 -52.0(2) . . . . ?
C2 C3 C4 C8 -170.39(18) . . . . ?
C2 C3 C4 C7 68.7(2) . . . . ?
C8 C4 C5 C6 173.27(18) . . . . ?
C7 C4 C5 C6 -66.0(2) . . . . ?
C3 C4 C5 C6 55.0(2) . . . . ?
C25 C1 C6 O2 2.1(3) . . . . ?
C2 C1 C6 O2 179.49(18) . . . . ?
C25 C1 C6 C5 -176.90(18) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C4 C5 C6 O2 149.88(19) . . . . ?
C4 C5 C6 C1 -31.1(3) . . . . ?
C26 C9 C10 O3 -4.9(3) . . . . ?
C14 C9 C10 O3 176.97(19) . . . . ?
C26 C9 C10 C11 174.15(18) . . . . ?
C14 C9 C10 C11 -4.0(3) . . . . ?
O3 C10 C11 C12 -146.9(2) . . . . ?
C9 C10 C11 C12 34.0(3) . . . . ?
C10 C11 C12 C15 63.9(2) . . . . ?
C10 C11 C12 C13 -57.4(2) . . . . ?
C10 C11 C12 C16 -175.63(17) . . . . ?
C15 C12 C13 C14 -66.0(2) . . . . ?
C11 C12 C13 C14 54.2(2) . . . . ?
C16 C12 C13 C14 173.18(17) . . . . ?
C26 C9 C14 O4 1.6(3) . . . . ?
C10 C9 C14 O4 179.69(18) . . . . ?
C26 C9 C14 C13 -177.51(17) . . . . ?
C10 C9 C14 C13 0.6(3) . . . . ?
C12 C13 C14 O4 153.44(18) . . . . ?
C12 C13 C14 C9 -27.4(3) . . . . ?
C27 C17 C18 O5 -3.5(3) . . . . ?
C22 C17 C18 O5 177.22(18) . . . . ?
C27 C17 C18 C19 175.17(18) . . . . ?
C22 C17 C18 C19 -4.1(3) . . . . ?
O5 C18 C19 C20 -149.12(19) . . . . ?
C17 C18 C19 C20 32.2(3) . . . . ?
C18 C19 C20 C23 64.5(2) . . . . ?
C18 C19 C20 C21 -55.9(2) . . . . ?
C18 C19 C20 C24 -174.96(18) . . . . ?
C23 C20 C21 C22 -65.3(2) . . . . ?
C19 C20 C21 C22 54.9(2) . . . . ?
C24 C20 C21 C22 173.95(17) . . . . ?
C27 C17 C22 O6 2.5(3) . . . . ?
C18 C17 C22 O6 -178.17(19) . . . . ?
C27 C17 C22 C21 -176.36(18) . . . . ?
C18 C17 C22 C21 3.0(3) . . . . ?
C20 C21 C22 O6 151.1(2) . . . . ?
C20 C21 C22 C17 -30.0(3) . . . . ?
C2 C1 C25 N1 -177.47(17) . . . . ?
C6 C1 C25 N1 -0.1(3) . . . . ?
C2 C1 C25 N3 1.7(3) . . . . ?
C6 C1 C25 N3 179.14(17) . . . . ?
C14 C9 C26 N2 1.1(3) . . . . ?
C10 C9 C26 N2 -177.05(17) . . . . ?
C14 C9 C26 N1 179.65(17) . . . . ?
C10 C9 C26 N1 1.5(3) . . . . ?
C18 C17 C27 N2 0.9(3) . . . . ?
C22 C17 C27 N2 -179.74(17) . . . . ?
C18 C17 C27 N3 -177.61(17) . . . . ?
C22 C17 C27 N3 1.7(3) . . . . ?
N3 C25 N1 C26 -1.4(3) . . . . ?
C1 C25 N1 C26 177.85(17) . . . . ?
N2 C26 N1 C25 2.1(3) . . . . ?
C9 C26 N1 C25 -176.61(17) . . . . ?
N3 C27 N2 C26 1.2(3) . . . . ?
C17 C27 N2 C26 -177.45(17) . . . . ?
N1 C26 N2 C27 -2.0(3) . . . . ?
C9 C26 N2 C27 176.72(18) . . . . ?
N2 C27 N3 C25 -0.4(3) . . . . ?
C17 C27 N3 C25 178.22(17) . . . . ?
N1 C25 N3 C27 0.5(3) . . . . ?
C1 C25 N3 C27 -178.73(17) . . . . ?

_refine_diff_density_max         1.097
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.080

####################################################################### 
# 
# 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_200424su
_database_code_depnum_ccdc_archive 'CCDC 2014520'
loop_
_audit_author_name
_audit_author_address
'Takayuki Tanaka'
;Kyoto University
Japan
;
_audit_update_record             
;
2020-07-07 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H33 N3 O6'
_chemical_formula_sum            'C27 H33 N3 O6'
_chemical_formula_weight         495.56

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

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

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

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

_cell_length_a                   17.963(2)
_cell_length_b                   7.3777(8)
_cell_length_c                   20.201(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.543(3)
_cell_angle_gamma                90
_cell_volume                     2579.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1518
_cell_measurement_theta_min      31.1
_cell_measurement_theta_max      71.8

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.743
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            16930
_diffrn_reflns_av_unetI/netI     0.0717
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.544
_diffrn_reflns_theta_max         66.993
_diffrn_reflns_theta_full        66.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4569
_reflns_number_gt                3035
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0120P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4569
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0752
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.69047(7) 0.50718(18) 0.16355(6) 0.0216(3) Uani 1 1 d . . . . .
O1 O 0.85229(7) 0.25676(18) 0.35670(6) 0.0215(3) Uani 1 1 d . . . . .
O3 O 0.92595(7) 0.75152(18) 0.26193(6) 0.0214(3) Uani 1 1 d . . . . .
O6 O 0.88209(8) 1.32200(19) 0.15550(7) 0.0300(3) Uani 1 1 d . . . . .
O5 O 0.48453(8) 0.2453(2) 0.23325(7) 0.0321(3) Uani 1 1 d . . . . .
O4 O 0.76110(8) -0.3311(2) 0.37353(7) 0.0314(4) Uani 1 1 d . . . . .
N2 N 0.76804(9) 0.3692(2) 0.25903(7) 0.0185(3) Uani 1 1 d . . . . .
N1 N 0.80559(9) 0.6371(2) 0.21011(7) 0.0187(3) Uani 1 1 d . . . . .
N3 N 0.89048(9) 0.5039(2) 0.31001(7) 0.0196(4) Uani 1 1 d . . . . .
C20 C 0.75744(11) 0.5025(3) 0.21292(8) 0.0186(4) Uani 1 1 d . . . . .
C21 C 0.83481(11) 0.3837(3) 0.30629(8) 0.0180(4) Uani 1 1 d . . . . .
C22 C 0.87102(11) 0.6244(3) 0.25912(9) 0.0188(4) Uani 1 1 d . . . . .
C23 C 0.63791(11) 0.3650(3) 0.16364(8) 0.0197(4) Uani 1 1 d . . . . .
C24 C 0.79323(11) 0.1393(3) 0.36430(8) 0.0207(4) Uani 1 1 d . . . . .
C25 C 0.90585(11) 1.0384(3) 0.21036(9) 0.0229(4) Uani 1 1 d . . . . .
H1 H 0.9002 1.0836 0.2528 0.027 Uiso 1 1 calc R U . . .
C26 C 0.80789(11) -0.0372(3) 0.36568(9) 0.0219(4) Uani 1 1 d . . . . .
H2 H 0.8552 -0.0790 0.3587 0.026 Uiso 1 1 calc R U . . .
C27 C 0.58437(11) 0.3861(3) 0.19763(9) 0.0228(4) Uani 1 1 d . . . . .
H3 H 0.5827 0.4940 0.2229 0.027 Uiso 1 1 calc R U . . .
C28 C 0.52810(11) 0.2415(3) 0.19565(9) 0.0241(4) Uani 1 1 d . . . . .
C29 C 0.91729(10) 0.8649(3) 0.20377(8) 0.0196(4) Uani 1 1 d . . . . .
C30 C 0.68738(11) 0.0993(3) 0.42283(9) 0.0213(4) Uani 1 1 d . . . . .
C31 C 0.75159(12) -0.1679(3) 0.37788(9) 0.0232(4) Uani 1 1 d . . . . .
C32 C 0.90152(11) 1.1651(3) 0.15287(9) 0.0220(4) Uani 1 1 d . . . . .
C33 C 0.72250(11) 0.2233(3) 0.37732(9) 0.0223(4) Uani 1 1 d . . . . .
H4 H 0.6837 0.2448 0.3329 0.027 Uiso 1 1 calc R U . . .
H5 H 0.7362 0.3418 0.4003 0.027 Uiso 1 1 calc R U . . .
C34 C 0.60479(11) 0.0362(3) 0.13678(9) 0.0226(4) Uani 1 1 d . . . . .
C35 C 0.92398(11) 1.0873(3) 0.09160(9) 0.0220(4) Uani 1 1 d . . . . .
H6 H 0.9808 1.0945 0.1002 0.026 Uiso 1 1 calc R U . . .
H7 H 0.9005 1.1621 0.0506 0.026 Uiso 1 1 calc R U . . .
C36 C 0.64560(11) 0.2067(3) 0.12033(9) 0.0227(4) Uani 1 1 d . . . . .
H8 H 0.7011 0.1796 0.1272 0.027 Uiso 1 1 calc R U . . .
H9 H 0.6236 0.2387 0.0714 0.027 Uiso 1 1 calc R U . . .
C37 C 0.81000(11) 0.8791(3) 0.05456(9) 0.0269(5) Uani 1 1 d . . . . .
H16 H 0.7937 0.7526 0.0458 0.040 Uiso 1 1 calc R U . . .
H17 H 0.7901 0.9504 0.0126 0.040 Uiso 1 1 calc R U . . .
H18 H 0.7896 0.9280 0.0913 0.040 Uiso 1 1 calc R U . . .
C38 C 0.89833(11) 0.8890(3) 0.07643(9) 0.0226(4) Uani 1 1 d . . . . .
C39 C 0.93074(11) 0.7738(3) 0.14150(9) 0.0217(4) Uani 1 1 d . . . . .
H10 H 0.9054 0.6535 0.1354 0.026 Uiso 1 1 calc R U . . .
H11 H 0.9869 0.7551 0.1483 0.026 Uiso 1 1 calc R U . . .
C40 C 0.73885(12) 0.1015(3) 0.49699(9) 0.0250(5) Uani 1 1 d . . . . .
H19 H 0.7165 0.0223 0.5255 0.038 Uiso 1 1 calc R U . . .
H20 H 0.7423 0.2254 0.5150 0.038 Uiso 1 1 calc R U . . .
H21 H 0.7906 0.0581 0.4978 0.038 Uiso 1 1 calc R U . . .
C41 C 0.65284(11) -0.0485(3) 0.20334(9) 0.0245(4) Uani 1 1 d . . . . .
H22 H 0.6252 -0.1530 0.2151 0.037 Uiso 1 1 calc R U . . .
H23 H 0.6616 0.0413 0.2404 0.037 Uiso 1 1 calc R U . . .
H24 H 0.7027 -0.0883 0.1973 0.037 Uiso 1 1 calc R U . . .
C42 C 0.52454(11) 0.0900(3) 0.14443(9) 0.0240(4) Uani 1 1 d . . . . .
H12 H 0.4915 0.1285 0.0991 0.029 Uiso 1 1 calc R U . . .
H13 H 0.5002 -0.0174 0.1593 0.029 Uiso 1 1 calc R U . . .
C43 C 0.67964(11) -0.0928(3) 0.39366(9) 0.0231(4) Uani 1 1 d . . . . .
H14 H 0.6650 -0.1746 0.4269 0.028 Uiso 1 1 calc R U . . .
H15 H 0.6369 -0.0944 0.3509 0.028 Uiso 1 1 calc R U . . .
C44 C 0.60692(12) 0.1713(3) 0.42129(10) 0.0293(5) Uani 1 1 d . . . . .
H25 H 0.5740 0.1692 0.3740 0.044 Uiso 1 1 calc R U . . .
H26 H 0.6113 0.2960 0.4386 0.044 Uiso 1 1 calc R U . . .
H27 H 0.5840 0.0948 0.4503 0.044 Uiso 1 1 calc R U . . .
C45 C 0.59469(12) -0.1024(3) 0.07801(9) 0.0294(5) Uani 1 1 d . . . . .
H28 H 0.6455 -0.1377 0.0732 0.044 Uiso 1 1 calc R U . . .
H29 H 0.5643 -0.0478 0.0350 0.044 Uiso 1 1 calc R U . . .
H30 H 0.5678 -0.2097 0.0885 0.044 Uiso 1 1 calc R U . . .
C46 C 0.93061(12) 0.8143(3) 0.01857(9) 0.0294(5) Uani 1 1 d . . . . .
H31 H 0.9871 0.8244 0.0321 0.044 Uiso 1 1 calc R U . . .
H32 H 0.9095 0.8843 -0.0235 0.044 Uiso 1 1 calc R U . . .
H33 H 0.9158 0.6868 0.0103 0.044 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
O2 C20 1.342(2) . ?
O2 C23 1.412(2) . ?
O1 C21 1.357(2) . ?
O1 C24 1.410(2) . ?
O3 C22 1.351(2) . ?
O3 C29 1.416(2) . ?
O6 C32 1.215(2) . ?
O5 C28 1.228(2) . ?
O4 C31 1.223(2) . ?
N2 C21 1.322(2) . ?
N2 C20 1.332(2) . ?
N1 C22 1.322(2) . ?
N1 C20 1.328(2) . ?
N3 C21 1.323(2) . ?
N3 C22 1.333(2) . ?
C23 C27 1.332(2) . ?
C23 C36 1.487(3) . ?
C24 C26 1.327(3) . ?
C24 C33 1.499(3) . ?
C25 C29 1.309(3) . ?
C25 C32 1.476(3) . ?
C25 H1 0.9500 . ?
C26 C31 1.465(3) . ?
C26 H2 0.9500 . ?
C27 C28 1.463(3) . ?
C27 H3 0.9500 . ?
C28 C42 1.513(3) . ?
C29 C39 1.502(2) . ?
C30 C43 1.527(3) . ?
C30 C44 1.532(3) . ?
C30 C40 1.535(3) . ?
C30 C33 1.546(2) . ?
C31 C43 1.516(3) . ?
C32 C35 1.514(2) . ?
C33 H4 0.9900 . ?
C33 H5 0.9900 . ?
C34 C41 1.524(3) . ?
C34 C36 1.537(3) . ?
C34 C45 1.540(3) . ?
C34 C42 1.542(3) . ?
C35 C38 1.540(3) . ?
C35 H6 0.9900 . ?
C35 H7 0.9900 . ?
C36 H8 0.9900 . ?
C36 H9 0.9900 . ?
C37 C38 1.531(3) . ?
C37 H16 0.9800 . ?
C37 H17 0.9800 . ?
C37 H18 0.9800 . ?
C38 C46 1.539(2) . ?
C38 C39 1.542(3) . ?
C39 H10 0.9900 . ?
C39 H11 0.9900 . ?
C40 H19 0.9800 . ?
C40 H20 0.9800 . ?
C40 H21 0.9800 . ?
C41 H22 0.9800 . ?
C41 H23 0.9800 . ?
C41 H24 0.9800 . ?
C42 H12 0.9900 . ?
C42 H13 0.9900 . ?
C43 H14 0.9900 . ?
C43 H15 0.9900 . ?
C44 H25 0.9800 . ?
C44 H26 0.9800 . ?
C44 H27 0.9800 . ?
C45 H28 0.9800 . ?
C45 H29 0.9800 . ?
C45 H30 0.9800 . ?
C46 H31 0.9800 . ?
C46 H32 0.9800 . ?
C46 H33 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
C20 O2 C23 116.52(14) . . ?
C21 O1 C24 118.46(14) . . ?
C22 O3 C29 117.28(14) . . ?
C21 N2 C20 112.17(16) . . ?
C22 N1 C20 111.93(16) . . ?
C21 N3 C22 111.42(16) . . ?
N1 C20 N2 127.51(17) . . ?
N1 C20 O2 114.41(16) . . ?
N2 C20 O2 118.07(16) . . ?
N2 C21 N3 128.36(17) . . ?
N2 C21 O1 117.96(16) . . ?
N3 C21 O1 113.60(16) . . ?
N1 C22 N3 128.43(17) . . ?
N1 C22 O3 118.36(16) . . ?
N3 C22 O3 113.14(16) . . ?
C27 C23 O2 119.27(18) . . ?
C27 C23 C36 126.07(18) . . ?
O2 C23 C36 114.53(14) . . ?
C26 C24 O1 117.03(17) . . ?
C26 C24 C33 125.06(17) . . ?
O1 C24 C33 117.60(17) . . ?
C29 C25 C32 121.04(16) . . ?
C29 C25 H1 119.5 . . ?
C32 C25 H1 119.5 . . ?
C24 C26 C31 120.48(18) . . ?
C24 C26 H2 119.8 . . ?
C31 C26 H2 119.8 . . ?
C23 C27 C28 119.30(19) . . ?
C23 C27 H3 120.4 . . ?
C28 C27 H3 120.4 . . ?
O5 C28 C27 121.07(19) . . ?
O5 C28 C42 121.53(19) . . ?
C27 C28 C42 117.38(16) . . ?
C25 C29 O3 118.60(16) . . ?
C25 C29 C39 125.99(17) . . ?
O3 C29 C39 115.08(17) . . ?
C43 C30 C44 109.04(17) . . ?
C43 C30 C40 110.79(16) . . ?
C44 C30 C40 109.53(14) . . ?
C43 C30 C33 109.20(14) . . ?
C44 C30 C33 108.41(16) . . ?
C40 C30 C33 109.82(16) . . ?
O4 C31 C26 121.35(18) . . ?
O4 C31 C43 121.20(18) . . ?
C26 C31 C43 117.42(17) . . ?
O6 C32 C25 121.60(16) . . ?
O6 C32 C35 122.66(17) . . ?
C25 C32 C35 115.73(17) . . ?
C24 C33 C30 111.11(16) . . ?
C24 C33 H4 109.4 . . ?
C30 C33 H4 109.4 . . ?
C24 C33 H5 109.4 . . ?
C30 C33 H5 109.4 . . ?
H4 C33 H5 108.0 . . ?
C41 C34 C36 109.66(16) . . ?
C41 C34 C45 109.25(17) . . ?
C36 C34 C45 109.95(14) . . ?
C41 C34 C42 109.93(14) . . ?
C36 C34 C42 108.91(16) . . ?
C45 C34 C42 109.14(16) . . ?
C32 C35 C38 113.05(15) . . ?
C32 C35 H6 109.0 . . ?
C38 C35 H6 109.0 . . ?
C32 C35 H7 109.0 . . ?
C38 C35 H7 109.0 . . ?
H6 C35 H7 107.8 . . ?
C23 C36 C34 112.99(14) . . ?
C23 C36 H8 109.0 . . ?
C34 C36 H8 109.0 . . ?
C23 C36 H9 109.0 . . ?
C34 C36 H9 109.0 . . ?
H8 C36 H9 107.8 . . ?
C38 C37 H16 109.5 . . ?
C38 C37 H17 109.5 . . ?
H16 C37 H17 109.5 . . ?
C38 C37 H18 109.5 . . ?
H16 C37 H18 109.5 . . ?
H17 C37 H18 109.5 . . ?
C37 C38 C46 109.64(16) . . ?
C37 C38 C35 109.55(17) . . ?
C46 C38 C35 109.74(15) . . ?
C37 C38 C39 110.18(15) . . ?
C46 C38 C39 108.47(16) . . ?
C35 C38 C39 109.24(15) . . ?
C29 C39 C38 111.01(16) . . ?
C29 C39 H10 109.4 . . ?
C38 C39 H10 109.4 . . ?
C29 C39 H11 109.4 . . ?
C38 C39 H11 109.4 . . ?
H10 C39 H11 108.0 . . ?
C30 C40 H19 109.5 . . ?
C30 C40 H20 109.5 . . ?
H19 C40 H20 109.5 . . ?
C30 C40 H21 109.5 . . ?
H19 C40 H21 109.5 . . ?
H20 C40 H21 109.5 . . ?
C34 C41 H22 109.5 . . ?
C34 C41 H23 109.5 . . ?
H22 C41 H23 109.5 . . ?
C34 C41 H24 109.5 . . ?
H22 C41 H24 109.5 . . ?
H23 C41 H24 109.5 . . ?
C28 C42 C34 112.91(16) . . ?
C28 C42 H12 109.0 . . ?
C34 C42 H12 109.0 . . ?
C28 C42 H13 109.0 . . ?
C34 C42 H13 109.0 . . ?
H12 C42 H13 107.8 . . ?
C31 C43 C30 115.19(16) . . ?
C31 C43 H14 108.5 . . ?
C30 C43 H14 108.5 . . ?
C31 C43 H15 108.5 . . ?
C30 C43 H15 108.5 . . ?
H14 C43 H15 107.5 . . ?
C30 C44 H25 109.5 . . ?
C30 C44 H26 109.5 . . ?
H25 C44 H26 109.5 . . ?
C30 C44 H27 109.5 . . ?
H25 C44 H27 109.5 . . ?
H26 C44 H27 109.5 . . ?
C34 C45 H28 109.5 . . ?
C34 C45 H29 109.5 . . ?
H28 C45 H29 109.5 . . ?
C34 C45 H30 109.5 . . ?
H28 C45 H30 109.5 . . ?
H29 C45 H30 109.5 . . ?
C38 C46 H31 109.5 . . ?
C38 C46 H32 109.5 . . ?
H31 C46 H32 109.5 . . ?
C38 C46 H33 109.5 . . ?
H31 C46 H33 109.5 . . ?
H32 C46 H33 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
C22 N1 C20 N2 2.2(2) . . . . ?
C22 N1 C20 O2 -178.98(15) . . . . ?
C21 N2 C20 N1 1.2(3) . . . . ?
C21 N2 C20 O2 -177.57(15) . . . . ?
C23 O2 C20 N1 178.90(15) . . . . ?
C23 O2 C20 N2 -2.2(2) . . . . ?
C20 N2 C21 N3 -3.9(3) . . . . ?
C20 N2 C21 O1 179.45(15) . . . . ?
C22 N3 C21 N2 2.6(3) . . . . ?
C22 N3 C21 O1 179.36(14) . . . . ?
C24 O1 C21 N2 -12.6(2) . . . . ?
C24 O1 C21 N3 170.29(15) . . . . ?
C20 N1 C22 N3 -3.9(3) . . . . ?
C20 N1 C22 O3 179.17(15) . . . . ?
C21 N3 C22 N1 1.8(3) . . . . ?
C21 N3 C22 O3 178.86(14) . . . . ?
C29 O3 C22 N1 -14.0(2) . . . . ?
C29 O3 C22 N3 168.64(14) . . . . ?
C20 O2 C23 C27 92.1(2) . . . . ?
C20 O2 C23 C36 -91.79(18) . . . . ?
C21 O1 C24 C26 127.90(18) . . . . ?
C21 O1 C24 C33 -58.2(2) . . . . ?
O1 C24 C26 C31 176.04(14) . . . . ?
C33 C24 C26 C31 2.6(3) . . . . ?
O2 C23 C27 C28 177.77(15) . . . . ?
C36 C23 C27 C28 2.2(3) . . . . ?
C23 C27 C28 O5 170.39(18) . . . . ?
C23 C27 C28 C42 -11.0(3) . . . . ?
C32 C25 C29 O3 175.95(16) . . . . ?
C32 C25 C29 C39 2.9(3) . . . . ?
C22 O3 C29 C25 115.07(19) . . . . ?
C22 O3 C29 C39 -71.1(2) . . . . ?
C24 C26 C31 O4 173.69(18) . . . . ?
C24 C26 C31 C43 -4.2(3) . . . . ?
C29 C25 C32 O6 171.29(19) . . . . ?
C29 C25 C32 C35 -9.6(3) . . . . ?
C26 C24 C33 C30 25.5(3) . . . . ?
O1 C24 C33 C30 -147.91(15) . . . . ?
C43 C30 C33 C24 -49.2(2) . . . . ?
C44 C30 C33 C24 -167.86(16) . . . . ?
C40 C30 C33 C24 72.50(19) . . . . ?
O6 C32 C35 C38 -144.29(19) . . . . ?
C25 C32 C35 C38 36.7(2) . . . . ?
C27 C23 C36 C34 -20.3(3) . . . . ?
O2 C23 C36 C34 163.88(15) . . . . ?
C41 C34 C36 C23 -76.1(2) . . . . ?
C45 C34 C36 C23 163.77(16) . . . . ?
C42 C34 C36 C23 44.2(2) . . . . ?
C32 C35 C38 C37 65.5(2) . . . . ?
C32 C35 C38 C46 -174.10(17) . . . . ?
C32 C35 C38 C39 -55.3(2) . . . . ?
C25 C29 C39 C38 -22.7(3) . . . . ?
O3 C29 C39 C38 164.02(15) . . . . ?
C37 C38 C39 C29 -73.6(2) . . . . ?
C46 C38 C39 C29 166.39(16) . . . . ?
C35 C38 C39 C29 46.8(2) . . . . ?
O5 C28 C42 C34 -143.59(19) . . . . ?
C27 C28 C42 C34 37.8(2) . . . . ?
C41 C34 C42 C28 66.7(2) . . . . ?
C36 C34 C42 C28 -53.5(2) . . . . ?
C45 C34 C42 C28 -173.55(16) . . . . ?
O4 C31 C43 C30 158.75(17) . . . . ?
C26 C31 C43 C30 -23.3(2) . . . . ?
C44 C30 C43 C31 167.74(15) . . . . ?
C40 C30 C43 C31 -71.64(19) . . . . ?
C33 C30 C43 C31 49.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C27 H3 O5 0.95 2.50 3.381(2) 154.0 2_655
C33 H5 O4 0.99 2.54 3.365(2) 140.8 1_565
C35 H6 N3 0.99 2.61 3.448(2) 141.8 2_755
C39 H10 O6 0.99 2.53 3.477(3) 159.5 1_545
C43 H15 O5 0.99 2.66 3.556(2) 151.0 2_645

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.047

