# 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. 
# 
#######################################################################

data_compound7
_audit_block_doi                 10.5517/ccdc.csd.cc23tth8
_database_code_depnum_ccdc_archive 'CCDC 1961230'
loop_
_audit_author_name
_audit_author_address
'Raffaella Soave'
;ISTM, CNR
Italy
;
_audit_update_record             
;
2019-11-13 deposited with the CCDC.	2020-03-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6


#------------------ CHEMICAL INFORMATION ------------------------------------#
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H38 N6 O8'
_chemical_formula_weight         478.55

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.156(2)
_cell_length_b                   11.413(2)
_cell_length_c                   11.888(2)
_cell_angle_alpha                90
_cell_angle_beta                 111.69(3)
_cell_angle_gamma                90
_cell_volume                     1280.3(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3496
_cell_measurement_theta_min      2.566
_cell_measurement_theta_max      22.244

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   0.7810
_exptl_transmission_factor_max   0.8623
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS; Sheldrick, 2004'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS APEX CCD area-detector'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22941
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.844
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7475
_reflns_number_gt                4289
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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       'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_cell_refinement       'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_data_reduction        'SAINT+ (Bruker AXS, Madison (USA) 1994-1996)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/4 (Sheldrick, 2014)'
_computing_molecular_graphics    'Diamond v3.2i (Brandenburg, 2012)'
_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)+(0.0622P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1616 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         7475
_refine_ls_number_parameters     319
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1200
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.964
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.001

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 0.7612(2) 0.08422(18) 0.73189(17) 0.0524(5) Uani 1 1 d . . . . .
O2 O 0.9834(2) 0.2964(2) 0.95416(16) 0.0542(5) Uani 1 1 d . . . . .
O3 O 0.7128(2) 0.1055(2) 1.20373(17) 0.0590(6) Uani 1 1 d . . . . .
O4 O 1.0004(2) 0.2252(2) 1.45402(16) 0.0577(6) Uani 1 1 d . . . . .
O5 O 0.6807(2) 0.3791(2) 1.02669(18) 0.0592(6) Uani 1 1 d . . . . .
O6 O 0.5597(3) 0.2754(2) 0.5192(2) 0.0753(7) Uani 1 1 d . . . . .
N2 N 0.8947(2) 0.1888(2) 0.65262(18) 0.0409(5) Uani 1 1 d . . . . .
H1 H 0.9022 0.2134 0.5869 0.049 Uiso 1 1 calc R U . . .
N3 N 0.8044(2) 0.3474(2) 0.78350(18) 0.0420(5) Uani 1 1 d . . . . .
H2 H 0.7691 0.3450 0.7057 0.050 Uiso 1 1 calc R U . . .
N5 N 0.8777(3) 0.1732(2) 1.13675(18) 0.0452(6) Uani 1 1 d . . . . .
H3 H 0.8980 0.1952 1.0759 0.054 Uiso 1 1 calc R U . . .
N1 N 0.6638(2) 0.1589(2) 0.42462(19) 0.0451(5) Uani 1 1 d . . . . .
H4 H 0.6927 0.1514 0.3655 0.054 Uiso 1 1 calc R U . . .
N6 N 0.8794(3) 0.3464(2) 1.3034(2) 0.0532(6) Uani 1 1 d . . . . .
H5A H 0.8630 0.3944 1.3524 0.064 Uiso 1 1 calc R U . . .
H5B H 0.8478 0.3611 1.2271 0.064 Uiso 1 1 calc R U . . .
N4 N 0.6779(2) 0.2192(2) 0.91331(19) 0.0433(5) Uani 1 1 d . . . . .
H6 H 0.6912 0.1930 0.8505 0.052 Uiso 1 1 calc R U . . .
C1 C 0.7870(3) 0.1167(2) 0.6435(2) 0.0401(6) Uani 1 1 d . . . . .
C2 C 0.9281(3) 0.2925(2) 0.8442(2) 0.0416(6) Uani 1 1 d . . . . .
C3 C 0.7448(3) 0.1398(3) 1.1192(2) 0.0449(6) Uani 1 1 d . . . . .
C4 C 0.9527(3) 0.2505(2) 1.3452(2) 0.0434(6) Uani 1 1 d . . . . .
C5 C 0.6947(3) 0.3343(3) 0.9377(2) 0.0438(6) Uani 1 1 d . . . . .
C6 C 0.5977(4) 0.4651(3) 0.7591(3) 0.0633(9) Uani 1 1 d . . . . .
H6A H 0.6228 0.5213 0.7103 0.095 Uiso 1 1 calc R U . . .
H6B H 0.5466 0.5036 0.8022 0.095 Uiso 1 1 calc R U . . .
H6C H 0.5392 0.4053 0.7080 0.095 Uiso 1 1 calc R U . . .
C7 C 0.6379(3) 0.1364(3) 0.9895(2) 0.0487(7) Uani 1 1 d . . . . .
C8 C 0.7003(3) 0.0698(2) 0.5180(2) 0.0431(6) Uani 1 1 d . . . . .
H8 H 0.6116 0.0387 0.5208 0.052 Uiso 1 1 calc R U . . .
C9 C 0.9872(3) 0.1726(3) 1.2564(2) 0.0492(7) Uani 1 1 d . . . . .
H9 H 0.9979 0.0921 1.2873 0.059 Uiso 1 1 calc R U . . .
C10 C 1.0005(3) 0.2284(3) 0.7683(2) 0.0423(6) Uani 1 1 d . . . . .
C11 C 0.7302(3) 0.4104(2) 0.8481(2) 0.0441(6) Uani 1 1 d . . . . .
H11 H 0.7921 0.4739 0.8936 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6458(5) 0.0116(3) 0.9429(3) 0.0733(11) Uani 1 1 d . . . . .
H12A H 0.5839 0.0059 0.8595 0.110 Uiso 1 1 calc R U . . .
H12B H 0.6170 -0.0439 0.9900 0.110 Uiso 1 1 calc R U . . .
H12C H 0.7413 -0.0048 0.9502 0.110 Uiso 1 1 calc R U . . .
C13 C 0.4890(4) 0.1637(4) 0.9848(3) 0.0781(11) Uani 1 1 d . . . . .
H13A H 0.4885 0.2392 1.0202 0.117 Uiso 1 1 calc R U . . .
H13B H 0.4605 0.1051 1.0291 0.117 Uiso 1 1 calc R U . . .
H13C H 0.4243 0.1640 0.9020 0.117 Uiso 1 1 calc R U . . .
C14 C 1.0957(3) 0.3174(3) 0.7405(3) 0.0587(8) Uani 1 1 d . . . . .
H14A H 1.1492 0.2792 0.6993 0.088 Uiso 1 1 calc R U . . .
H14B H 1.1594 0.3510 0.8146 0.088 Uiso 1 1 calc R U . . .
H14C H 1.0386 0.3782 0.6898 0.088 Uiso 1 1 calc R U . . .
C15 C 0.7764(4) -0.0300(3) 0.4850(3) 0.0577(8) Uani 1 1 d . . . . .
H15A H 0.7206 -0.0577 0.4053 0.087 Uiso 1 1 calc R U . . .
H15B H 0.7904 -0.0926 0.5423 0.087 Uiso 1 1 calc R U . . .
H15C H 0.8666 -0.0033 0.4864 0.087 Uiso 1 1 calc R U . . .
C16 C 0.5349(4) 0.3287(3) 0.3180(3) 0.0723(10) Uani 1 1 d . . . . .
H16A H 0.4380 0.3100 0.2707 0.108 Uiso 1 1 calc R U . . .
H16B H 0.5921 0.3155 0.2705 0.108 Uiso 1 1 calc R U . . .
H16C H 0.5417 0.4095 0.3420 0.108 Uiso 1 1 calc R U . . .
C17 C 0.5860(3) 0.2528(3) 0.4280(3) 0.0534(7) Uani 1 1 d . . . . .
C18 C 1.0872(3) 0.1259(3) 0.8400(3) 0.0601(8) Uani 1 1 d . . . . .
H18A H 1.0258 0.0718 0.8587 0.090 Uiso 1 1 calc R U . . .
H18B H 1.1575 0.1543 0.9138 0.090 Uiso 1 1 calc R U . . .
H18C H 1.1330 0.0870 0.7928 0.090 Uiso 1 1 calc R U . . .
C19 C 1.1276(3) 0.2106(4) 1.2495(3) 0.0737(10) Uani 1 1 d . . . . .
H19A H 1.1518 0.1590 1.1964 0.111 Uiso 1 1 calc R U . . .
H19B H 1.2004 0.2076 1.3289 0.111 Uiso 1 1 calc R U . . .
H19C H 1.1192 0.2892 1.2190 0.111 Uiso 1 1 calc R U . . .
OW1 O 1.1732(3) 0.0241(3) 1.5426(3) 0.1088(11) Uani 1 1 d D . . . .
HW1 H 1.258(3) 0.068(5) 1.582(5) 0.163 Uiso 1 1 d D U . . .
HW2 H 1.106(4) 0.077(4) 1.496(5) 0.163 Uiso 1 1 d D U . . .
OW2 O 0.4230(4) 0.1502(5) 0.6390(3) 0.1388(16) Uani 1 1 d D . . . .
HW3 H 0.433(8) 0.197(6) 0.579(4) 0.208 Uiso 1 1 d D U . . .
HW4 H 0.469(7) 0.183(6) 0.716(3) 0.208 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.231(3) . ?
O2 C2 1.219(3) . ?
O3 C3 1.229(3) . ?
O4 C4 1.237(3) . ?
O5 C5 1.230(3) . ?
O6 C17 1.236(4) . ?
N2 C1 1.341(3) . ?
N2 C10 1.469(3) . ?
N2 H1 0.8600 . ?
N3 C2 1.350(4) . ?
N3 C11 1.450(3) . ?
N3 H2 0.8600 . ?
N5 C3 1.342(4) . ?
N5 C9 1.447(3) . ?
N5 H3 0.8600 . ?
N1 C17 1.340(4) . ?
N1 C8 1.450(4) . ?
N1 H4 0.8600 . ?
N6 C4 1.313(4) . ?
N6 H5A 0.8600 . ?
N6 H5B 0.8600 . ?
N4 C5 1.342(4) . ?
N4 C7 1.467(4) . ?
N4 H6 0.8600 . ?
C1 C8 1.522(4) . ?
C2 C10 1.542(4) . ?
C3 C7 1.523(4) . ?
C4 C9 1.516(4) . ?
C5 C11 1.518(4) . ?
C6 C11 1.506(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C13 1.524(5) . ?
C7 C12 1.541(5) . ?
C8 C15 1.507(4) . ?
C8 H8 0.9800 . ?
C9 C19 1.521(5) . ?
C9 H9 0.9800 . ?
C10 C18 1.522(4) . ?
C10 C14 1.521(4) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.493(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
OW1 HW1 0.955(19) . ?
OW1 HW2 0.924(19) . ?
OW2 HW3 0.931(19) . ?
OW2 HW4 0.936(19) . ?

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
C1 N2 C10 123.9(2) . . ?
C1 N2 H1 118.1 . . ?
C10 N2 H1 118.1 . . ?
C2 N3 C11 120.7(2) . . ?
C2 N3 H2 119.6 . . ?
C11 N3 H2 119.6 . . ?
C3 N5 C9 121.0(2) . . ?
C3 N5 H3 119.5 . . ?
C9 N5 H3 119.5 . . ?
C17 N1 C8 121.6(2) . . ?
C17 N1 H4 119.2 . . ?
C8 N1 H4 119.2 . . ?
C4 N6 H5A 120.0 . . ?
C4 N6 H5B 120.0 . . ?
H5A N6 H5B 120.0 . . ?
C5 N4 C7 122.6(2) . . ?
C5 N4 H6 118.7 . . ?
C7 N4 H6 118.7 . . ?
O1 C1 N2 122.7(2) . . ?
O1 C1 C8 120.1(2) . . ?
N22 C1 C8 117.1(2) . . ?
O2 C2 N3 121.6(3) . . ?
O2 C2 C10 121.0(2) . . ?
N3 C2 C10 117.3(2) . . ?
O3 C3 N5 121.2(3) . . ?
O3 C3 C7 121.0(2) . . ?
N5 C3 C7 117.6(2) . . ?
O4 C4 N6 122.5(3) . . ?
O4 C4 C9 119.3(3) . . ?
N6 C4 C9 118.1(2) . . ?
O5 C5 N4 123.2(3) . . ?
O5 C5 C11 119.9(3) . . ?
N4 C5 C11 116.9(2) . . ?
C11 C6 H6A 109.5 . . ?
C11 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C11 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N4 C7 C13 110.1(3) . . ?
N4 C7 C3 110.6(2) . . ?
C13 C7 C3 111.0(3) . . ?
N4 C7 C12 108.1(2) . . ?
C13 C7 C12 111.0(3) . . ?
C3 C7 C12 106.0(3) . . ?
N1 C8 C15 110.0(2) . . ?
N1 C8 C1 113.3(2) . . ?
C15 C8 C1 110.8(2) . . ?
N1 C8 H8 107.5 . . ?
C15 C8 H8 107.5 . . ?
C1 C8 H8 107.5 . . ?
N5 C9 C4 113.0(2) . . ?
N5 C9 C19 109.9(2) . . ?
C4 C9 C19 109.4(3) . . ?
N5 C9 H9 108.1 . . ?
C4 C9 H9 108.1 . . ?
C19 C9 H9 108.1 . . ?
N2 C10 C18 111.1(2) . . ?
N2 C10 C14 107.8(2) . . ?
C18 C10 C14 110.6(3) . . ?
N2 C10 C2 110.6(2) . . ?
C18 C10 C2 109.8(2) . . ?
C14 C10 C2 106.8(2) . . ?
N3 C11 C6 109.7(2) . . ?
N3 C11 C5 113.1(2) . . ?
C6 C11 C5 110.3(2) . . ?
N3 C11 H11 107.8 . . ?
C6 C11 H11 107.8 . . ?
C5 C11 H11 107.8 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O6 C17 N1 120.9(3) . . ?
O6 C17 C16 122.0(3) . . ?
N1 C17 C16 117.1(3) . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
HW1 OW1 HW2 107(3) . . ?
HW3 OW2 HW4 112(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
C10 N2 C1 O1 5.7(4) . . . . ?
C10 N2 C1 C8 -171.0(2) . . . . ?
C11 N3 C2 O2 -2.0(4) . . . . ?
C11 N3 C2 C10 -179.5(2) . . . . ?
C9 N5 C3 O3 -1.6(4) . . . . ?
C9 N5 C3 C7 -176.6(3) . . . . ?
C7 N4 C5 O5 1.5(4) . . . . ?
C7 N4 C5 C11 -177.5(2) . . . . ?
C5 N4 C7 C13 65.2(4) . . . . ?
C5 N4 C7 C3 -57.9(4) . . . . ?
C5 N4 C7 C12 -173.5(3) . . . . ?
O3 C3 C7 N4 158.5(3) . . . . ?
N5 C3 C7 N4 -26.4(4) . . . . ?
O3 C3 C7 C13 36.0(4) . . . . ?
N5 C3 C7 C13 -148.9(3) . . . . ?
O3 C3 C7 C12 -84.6(3) . . . . ?
N5 C3 C7 C12 90.5(3) . . . . ?
C17 N1 C8 C15 174.9(3) . . . . ?
C17 N1 C8 C1 -60.6(3) . . . . ?
O1 C1 C8 N1 138.2(3) . . . . ?
N2 C1 C8 N1 -45.0(3) . . . . ?
O1 C1 C8 C15 -97.7(3) . . . . ?
N2 C1 C8 C15 79.1(3) . . . . ?
C3 N5 C9 C4 -59.2(3) . . . . ?
C3 N5 C9 C19 178.3(3) . . . . ?
O4 C4 C9 N5 150.8(3) . . . . ?
N6 C4 C9 N5 -33.1(4) . . . . ?
O4 C4 C9 C19 -86.3(3) . . . . ?
N6 C4 C9 C19 89.8(3) . . . . ?
C1 N2 C10 C18 63.8(3) . . . . ?
C1 N2 C10 C14 -174.8(3) . . . . ?
C1 N2 C10 C2 -58.4(3) . . . . ?
O2 C2 C10 N2 154.2(3) . . . . ?
N3 C2 C10 N2 -28.2(3) . . . . ?
O2 C2 C10 C18 31.3(4) . . . . ?
N3 C2 C10 C18 -151.2(3) . . . . ?
O2 C2 C10 C14 -88.8(3) . . . . ?
N3 C2 C10 C14 88.8(3) . . . . ?
C2 N3 C11 C6 178.8(3) . . . . ?
C2 N3 C11 C5 -57.5(3) . . . . ?
O5 C5 C11 N3 153.6(3) . . . . ?
N4 C5 C11 N3 -27.4(3) . . . . ?
O5 C5 C11 C6 -83.0(3) . . . . ?
N4 C5 C11 C6 96.0(3) . . . . ?
C8 N1 C17 O6 10.4(4) . . . . ?
C8 N1 C17 C16 -170.3(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
N2 H1 O4 0.86 2.16 2.962(3) 154.8 1_554
N3 H2 O6 0.86 2.57 3.309(4) 145.2 .
N5 H3 O2 0.86 2.26 3.093(3) 163.0 .
N1 H4 O3 0.86 2.08 2.912(3) 164.3 1_554
N6 H5A OW1 0.86 2.05 2.911(4) 173.5 2_758
N6 H5B O5 0.86 2.37 3.182(3) 158.0 .
N4 H6 O1 0.86 2.19 3.015(3) 161.9 .
C13 H13A O5 0.96 2.50 3.060(5) 117.1 .
C18 H18A O1 0.96 2.55 3.114(4) 117.4 .
OW1 HW1 OW2 0.955(19) 1.82(2) 2.770(5) 173(6) 1_656
OW1 HW2 O4 0.924(19) 1.97(3) 2.844(4) 158(5) .
OW2 HW3 O6 0.931(19) 1.90(4) 2.731(5) 147(6) .
OW2 HW4 N4 0.936(19) 2.55(4) 3.423(4) 155(6) .

_refine_diff_density_max         0.163
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.035

_shelxl_version_number           2014/6

