# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_KI_lab_011
_audit_block_doi                 10.5517/ccdc.csd.cc2229p5
_database_code_depnum_ccdc_archive 'CCDC 1908846'
loop_
_audit_author_name
_audit_author_address
'Yuichiro Mutoh'
;Kagawa University
Japan
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2019-08-06 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         ?
_chemical_formula_sum            'C20 H18 N6 O5'
_chemical_formula_weight         422.40

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           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                   15.311(2)
_cell_length_b                   14.370(2)
_cell_length_c                   8.7464(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.020(2)
_cell_angle_gamma                90
_cell_volume                     1924.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)

_cell_measurement_reflns_used    4228

_cell_measurement_theta_min      2.66

_cell_measurement_theta_max      28.10


_exptl_crystal_description       prism

_exptl_crystal_colour            orange

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.927

_exptl_absorpt_correction_T_max  0.996

_exptl_absorpt_process_details   'SADABS 2015/'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            21107
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.330
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4391
_reflns_number_gt                3338
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'

_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0350P)²+0.5691P] 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         4391
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0804
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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
O1 O 0.67439(6) 0.61556(6) 0.16104(10) 0.0179(2) Uani 1 1 d . . . . .
O2 O 0.75460(6) 0.52695(7) 0.36306(10) 0.0194(2) Uani 1 1 d . . . . .
O3 O 0.93325(6) 0.54836(7) 0.33629(11) 0.0229(2) Uani 1 1 d . . . . .
O4 O 0.76669(6) 0.73453(7) -0.04121(11) 0.0245(2) Uani 1 1 d . . . . .
O5 O 0.92538(7) 0.63635(7) 0.03793(11) 0.0265(2) Uani 1 1 d . . . . .
N1 N 0.52679(7) 0.57099(8) 0.71964(13) 0.0168(2) Uani 1 1 d . . . . .
N2 N 0.43532(7) 0.67732(7) 0.49139(13) 0.0163(2) Uani 1 1 d . . . . .
N3 N 0.32487(7) 0.70359(8) 0.66203(13) 0.0174(2) Uani 1 1 d . . . . .
N4 N 0.41072(7) 0.58734(8) 0.88062(13) 0.0177(3) Uani 1 1 d . . . . .
N5 N 0.25477(9) 0.57631(9) 1.15177(15) 0.0273(3) Uani 1 1 d . . . . .
N6 N 0.14798(8) 0.76489(9) 0.87600(15) 0.0276(3) Uani 1 1 d . . . . .
C1 C 0.63022(9) 0.61072(9) 0.29054(15) 0.0157(3) Uani 1 1 d . . . . .
C2 C 0.44736(9) 0.60750(9) 0.74411(15) 0.0160(3) Uani 1 1 d . . . . .
C3 C 0.40284(9) 0.66276(9) 0.63173(15) 0.0161(3) Uani 1 1 d . . . . .
C4 C 0.29230(9) 0.68586(9) 0.79720(16) 0.0173(3) Uani 1 1 d . . . . .
C5 C 0.51224(9) 0.63751(9) 0.46369(15) 0.0156(3) Uani 1 1 d . . . . .
C6 C 0.54981(9) 0.64708(9) 0.31751(15) 0.0160(3) Uani 1 1 d . . . . .
H6 H 0.5188 0.6789 0.2383 0.019 Uiso 1 1 calc R U . . .
C7 C 0.55976(9) 0.58551(9) 0.58215(15) 0.0156(3) Uani 1 1 d . . . . .
C8 C 0.67803(9) 0.55996(9) 0.41012(15) 0.0162(3) Uani 1 1 d . . . . .
C9 C 0.33405(9) 0.62482(9) 0.90454(15) 0.0175(3) Uani 1 1 d . . . . .
C10 C 0.63505(9) 0.66385(10) 0.03286(15) 0.0188(3) Uani 1 1 d . . . . .
H10 H 0.6166 0.7271 0.0635 0.023 Uiso 1 1 calc R U . . .
H10A H 0.5831 0.6295 -0.0059 0.023 Uiso 1 1 calc R U . . .
C11 C 0.21140(9) 0.73049(10) 0.83763(16) 0.0199(3) Uani 1 1 d . . . . .
C12 C 0.70296(9) 0.66927(10) -0.08774(15) 0.0191(3) Uani 1 1 d . . . . .
H12 H 0.7302 0.6075 -0.1020 0.023 Uiso 1 1 calc R U . . .
H12A H 0.6758 0.6887 -0.1862 0.023 Uiso 1 1 calc R U . . .
C13 C 0.64338(9) 0.54827(9) 0.55031(15) 0.0167(3) Uani 1 1 d . . . . .
H13 H 0.6750 0.5152 0.6273 0.020 Uiso 1 1 calc R U . . .
C14 C 0.29058(9) 0.59905(10) 1.04435(17) 0.0206(3) Uani 1 1 d . . . . .
C15 C 0.89635(9) 0.46528(10) 0.39253(17) 0.0230(3) Uani 1 1 d . . . . .
H15 H 0.9384 0.4336 0.4624 0.028 Uiso 1 1 calc R U . . .
H15A H 0.8821 0.4226 0.3067 0.028 Uiso 1 1 calc R U . . .
C16 C 0.81496(9) 0.48999(10) 0.47644(16) 0.0212(3) Uani 1 1 d . . . . .
H16 H 0.7901 0.4342 0.5257 0.025 Uiso 1 1 calc R U . . .
H16A H 0.8278 0.5371 0.5563 0.025 Uiso 1 1 calc R U . . .
C17 C 1.00254(10) 0.62286(12) 0.12798(17) 0.0286(4) Uani 1 1 d . . . . .
H17 H 1.0110 0.6759 0.1989 0.034 Uiso 1 1 calc R U . . .
H17A H 1.0539 0.6193 0.0611 0.034 Uiso 1 1 calc R U . . .
C18 C 0.92342(10) 0.72513(12) -0.03295(18) 0.0290(4) Uani 1 1 d . . . . .
H18 H 0.9763 0.7335 -0.0951 0.035 Uiso 1 1 calc R U . . .
H18A H 0.9229 0.7744 0.0461 0.035 Uiso 1 1 calc R U . . .
C19 C 0.84330(10) 0.73295(12) -0.13315(17) 0.0289(4) Uani 1 1 d . . . . .
H19 H 0.8462 0.7907 -0.1947 0.035 Uiso 1 1 calc R U . . .
H19A H 0.8404 0.6794 -0.2043 0.035 Uiso 1 1 calc R U . . .
C20 C 0.99396(10) 0.53435(12) 0.21673(17) 0.0287(4) Uani 1 1 d . . . . .
H20 H 0.9732 0.4838 0.1483 0.034 Uiso 1 1 calc R U . . .
H20A H 1.0515 0.5161 0.2606 0.034 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
O1 C1 1.3314(16) . ?
O1 C10 1.4412(16) . ?
O2 C8 1.3364(16) . ?
O2 C16 1.4446(16) . ?
O3 C15 1.4130(18) . ?
O3 C20 1.4257(17) . ?
O4 C12 1.4083(16) . ?
O4 C19 1.4341(17) . ?
O5 C18 1.4185(19) . ?
O5 C17 1.4215(18) . ?
N1 C7 1.3289(17) . ?
N1 C2 1.3451(17) . ?
N2 C5 1.3353(17) . ?
N2 C3 1.3489(17) . ?
N3 C4 1.3162(18) . ?
N3 C3 1.3603(17) . ?
N4 C9 1.3118(18) . ?
N4 C2 1.3594(17) . ?
N5 C14 1.1438(18) . ?
N6 C11 1.1452(18) . ?
C1 C6 1.3619(19) . ?
C1 C8 1.4609(19) . ?
C2 C3 1.4274(18) . ?
C4 C9 1.4277(19) . ?
C4 C11 1.4443(19) . ?
C5 C6 1.4180(19) . ?
C5 C7 1.4611(18) . ?
C6 H6 0.9500 . ?
C7 C13 1.4198(19) . ?
C8 C13 1.3551(19) . ?
C9 C14 1.451(2) . ?
C10 C12 1.4963(19) . ?
C10 H10 0.9900 . ?
C10 H10A 0.9900 . ?
C12 H12 0.9900 . ?
C12 H12A 0.9900 . ?
C13 H13 0.9500 . ?
C15 C16 1.500(2) . ?
C15 H15 0.9900 . ?
C15 H15A 0.9900 . ?
C16 H16 0.9900 . ?
C16 H16A 0.9900 . ?
C17 C20 1.497(2) . ?
C17 H17 0.9900 . ?
C17 H17A 0.9900 . ?
C18 C19 1.499(2) . ?
C18 H18 0.9900 . ?
C18 H18A 0.9900 . ?
C19 H19 0.9900 . ?
C19 H19A 0.9900 . ?
C20 H20 0.9900 . ?
C20 H20A 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
C1 O1 C10 118.38(10) . . ?
C8 O2 C16 118.23(10) . . ?
C15 O3 C20 113.95(11) . . ?
C12 O4 C19 113.38(11) . . ?
C18 O5 C17 112.07(12) . . ?
C7 N1 C2 116.22(11) . . ?
C5 N2 C3 116.06(11) . . ?
C4 N3 C3 116.06(12) . . ?
C9 N4 C2 115.92(12) . . ?
O1 C1 C6 126.99(12) . . ?
O1 C1 C8 112.31(11) . . ?
C6 C1 C8 120.70(12) . . ?
N1 C2 N4 116.42(12) . . ?
N1 C2 C3 121.97(12) . . ?
N4 C2 C3 121.59(12) . . ?
N2 C3 N3 116.71(12) . . ?
N2 C3 C2 122.25(12) . . ?
N3 C3 C2 121.05(12) . . ?
N3 C4 C9 122.49(13) . . ?
N3 C4 C11 118.32(12) . . ?
C9 C4 C11 119.19(12) . . ?
N2 C5 C6 119.69(12) . . ?
N2 C5 C7 121.35(12) . . ?
C6 C5 C7 118.95(12) . . ?
C1 C6 C5 120.10(12) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
N1 C7 C13 118.48(12) . . ?
N1 C7 C5 121.97(12) . . ?
C13 C7 C5 119.55(12) . . ?
O2 C8 C13 126.46(12) . . ?
O2 C8 C1 112.82(11) . . ?
C13 C8 C1 120.69(12) . . ?
N4 C9 C4 122.61(13) . . ?
N4 C9 C14 117.06(12) . . ?
C4 C9 C14 120.29(12) . . ?
O1 C10 C12 106.70(11) . . ?
O1 C10 H10 110.4 . . ?
C12 C10 H10 110.4 . . ?
O1 C10 H10A 110.4 . . ?
C12 C10 H10A 110.4 . . ?
H10 C10 H10A 108.6 . . ?
N6 C11 C4 177.11(15) . . ?
O4 C12 C10 108.52(11) . . ?
O4 C12 H12 110.0 . . ?
C10 C12 H12 110.0 . . ?
O4 C12 H12A 110.0 . . ?
C10 C12 H12A 110.0 . . ?
H12 C12 H12A 108.4 . . ?
C8 C13 C7 119.98(12) . . ?
C8 C13 H13 120.0 . . ?
C7 C13 H13 120.0 . . ?
N5 C14 C9 177.58(16) . . ?
O3 C15 C16 108.13(12) . . ?
O3 C15 H15 110.1 . . ?
C16 C15 H15 110.1 . . ?
O3 C15 H15A 110.1 . . ?
C16 C15 H15A 110.1 . . ?
H15 C15 H15A 108.4 . . ?
O2 C16 C15 106.14(11) . . ?
O2 C16 H16 110.5 . . ?
C15 C16 H16 110.5 . . ?
O2 C16 H16A 110.5 . . ?
C15 C16 H16A 110.5 . . ?
H16 C16 H16A 108.7 . . ?
O5 C17 C20 108.87(13) . . ?
O5 C17 H17 109.9 . . ?
C20 C17 H17 109.9 . . ?
O5 C17 H17A 109.9 . . ?
C20 C17 H17A 109.9 . . ?
H17 C17 H17A 108.3 . . ?
O5 C18 C19 109.50(13) . . ?
O5 C18 H18 109.8 . . ?
C19 C18 H18 109.8 . . ?
O5 C18 H18A 109.8 . . ?
C19 C18 H18A 109.8 . . ?
H18 C18 H18A 108.2 . . ?
O4 C19 C18 110.02(12) . . ?
O4 C19 H19 109.7 . . ?
C18 C19 H19 109.7 . . ?
O4 C19 H19A 109.7 . . ?
C18 C19 H19A 109.7 . . ?
H19 C19 H19A 108.2 . . ?
O3 C20 C17 108.95(12) . . ?
O3 C20 H20 109.9 . . ?
C17 C20 H20 109.9 . . ?
O3 C20 H20A 109.9 . . ?
C17 C20 H20A 109.9 . . ?
H20 C20 H20A 108.3 . . ?

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
C10 O1 C1 C6 -0.05(19) . . . . ?
C10 O1 C1 C8 -179.94(11) . . . . ?
C7 N1 C2 N4 175.53(11) . . . . ?
C7 N1 C2 C3 -3.10(18) . . . . ?
C9 N4 C2 N1 178.68(12) . . . . ?
C9 N4 C2 C3 -2.68(19) . . . . ?
C5 N2 C3 N3 179.43(11) . . . . ?
C5 N2 C3 C2 -0.50(18) . . . . ?
C4 N3 C3 N2 177.45(12) . . . . ?
C4 N3 C3 C2 -2.61(18) . . . . ?
N1 C2 C3 N2 3.8(2) . . . . ?
N4 C2 C3 N2 -174.72(12) . . . . ?
N1 C2 C3 N3 -176.09(12) . . . . ?
N4 C2 C3 N3 5.4(2) . . . . ?
C3 N3 C4 C9 -2.23(19) . . . . ?
C3 N3 C4 C11 177.52(12) . . . . ?
C3 N2 C5 C6 178.18(12) . . . . ?
C3 N2 C5 C7 -3.06(18) . . . . ?
O1 C1 C6 C5 -178.66(12) . . . . ?
C8 C1 C6 C5 1.22(19) . . . . ?
N2 C5 C6 C1 176.70(12) . . . . ?
C7 C5 C6 C1 -2.10(19) . . . . ?
C2 N1 C7 C13 -179.88(12) . . . . ?
C2 N1 C7 C5 -0.49(18) . . . . ?
N2 C5 C7 N1 3.79(19) . . . . ?
C6 C5 C7 N1 -177.43(12) . . . . ?
N2 C5 C7 C13 -176.82(12) . . . . ?
C6 C5 C7 C13 1.95(18) . . . . ?
C16 O2 C8 C13 -12.4(2) . . . . ?
C16 O2 C8 C1 169.22(11) . . . . ?
O1 C1 C8 O2 -1.80(16) . . . . ?
C6 C1 C8 O2 178.30(12) . . . . ?
O1 C1 C8 C13 179.75(12) . . . . ?
C6 C1 C8 C13 -0.2(2) . . . . ?
C2 N4 C9 C4 -2.19(19) . . . . ?
C2 N4 C9 C14 175.61(12) . . . . ?
N3 C4 C9 N4 5.0(2) . . . . ?
C11 C4 C9 N4 -174.77(13) . . . . ?
N3 C4 C9 C14 -172.76(12) . . . . ?
C11 C4 C9 C14 7.49(19) . . . . ?
C1 O1 C10 C12 172.66(11) . . . . ?
C19 O4 C12 C10 168.88(11) . . . . ?
O1 C10 C12 O4 -72.48(13) . . . . ?
O2 C8 C13 C7 -178.21(12) . . . . ?
C1 C8 C13 C7 0.0(2) . . . . ?
N1 C7 C13 C8 178.49(12) . . . . ?
C5 C7 C13 C8 -0.92(19) . . . . ?
C20 O3 C15 C16 -161.60(11) . . . . ?
C8 O2 C16 C15 -175.89(11) . . . . ?
O3 C15 C16 O2 65.32(14) . . . . ?
C18 O5 C17 C20 171.74(12) . . . . ?
C17 O5 C18 C19 176.72(12) . . . . ?
C12 O4 C19 C18 -128.66(13) . . . . ?
O5 C18 C19 O4 67.85(17) . . . . ?
C15 O3 C20 C17 158.80(12) . . . . ?
O5 C17 C20 O3 -72.83(15) . . . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043


_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  ?
_chemical_absolute_configuration ?
####################################################################### 
# 
# 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_Isoda1
_audit_block_doi                 10.5517/ccdc.csd.cc2229q6
_database_code_depnum_ccdc_archive 'CCDC 1908847'
loop_
_audit_author_name
_audit_author_address
'Yuichiro Mutoh'
;Kagawa University
Japan
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 N6 Na O5'
_chemical_formula_weight         445.39

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'
Na Na 0.0362 0.0249 '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                   15.823(6)
_cell_length_b                   7.751(3)
_cell_length_c                   16.592(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.807(6)
_cell_angle_gamma                90
_cell_volume                     2016.0(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)

_cell_measurement_reflns_used    1411

_cell_measurement_theta_min      2.60

_cell_measurement_theta_max      25.74


_exptl_crystal_description       platelet

_exptl_crystal_colour            purple

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             924
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.686

_exptl_absorpt_correction_T_max  0.996

_exptl_absorpt_process_details   'SADABS 2014/5'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            10720
_diffrn_reflns_av_unetI/netI     0.1096
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.299
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4485
_reflns_number_gt                2586
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'

_computing_publication_material  
;Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)
;

_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)+(0.0709P)²+0.3856P] 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         4485
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1750
_refine_ls_wR_factor_gt          0.1440
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.04859(17) 0.3185(4) 0.44090(17) 0.0324(7) Uani 1 1 d . . . . .
C1 C 0.1161(2) 0.3727(4) 0.45207(19) 0.0253(7) Uani 1 1 d . . . . .
C2 C 0.20155(18) 0.4447(4) 0.46380(18) 0.0228(7) Uani 1 1 d . . . . .
N2 N 0.25542(15) 0.3868(3) 0.52783(15) 0.0225(6) Uani 1 1 d . . . . .
C3 C 0.33309(17) 0.4646(4) 0.53972(18) 0.0207(6) Uani 1 1 d . . . . .
N3 N 0.38652(15) 0.4091(3) 0.60299(15) 0.0215(6) Uani 1 1 d . . . . .
C4 C 0.46265(18) 0.4945(4) 0.61874(18) 0.0216(7) Uani 1 1 d . . . . .
C5 C 0.52208(18) 0.4400(4) 0.68445(19) 0.0233(7) Uani 1 1 d . . . . .
H1 H 0.510160 0.342386 0.715667 0.028 Uiso 1 1 calc R U . . .
C6 C 0.59696(18) 0.5275(4) 0.70332(19) 0.0239(7) Uani 1 1 d . . . . .
O1 O 0.66076(13) 0.4895(3) 0.76463(13) 0.0263(5) Uani 1 1 d . . . . .
C7 C 0.65769(19) 0.3272(4) 0.8063(2) 0.0281(7) Uani 1 1 d . . . . .
H2 H 0.645697 0.231693 0.766727 0.034 Uiso 1 1 calc R U . . .
H3 H 0.612610 0.328921 0.842216 0.034 Uiso 1 1 calc R U . . .
C8 C 0.74323(19) 0.3049(4) 0.85495(19) 0.0258(7) Uani 1 1 d . . . . .
H4 H 0.746176 0.192794 0.883790 0.031 Uiso 1 1 calc R U . . .
H5 H 0.788107 0.306873 0.818787 0.031 Uiso 1 1 calc R U . . .
O2 O 0.75596(12) 0.4429(3) 0.91212(13) 0.0265(5) Uani 1 1 d . . . . .
C9 C 0.84105(19) 0.4493(4) 0.95510(19) 0.0283(7) Uani 1 1 d . . . . .
H6 H 0.858930 0.331180 0.972639 0.034 Uiso 1 1 calc R U . . .
H7 H 0.841030 0.520657 1.004570 0.034 Uiso 1 1 calc R U . . .
C11 C 0.93056(19) 0.7800(4) 0.8346(2) 0.0296(8) Uani 1 1 d . . . . .
H8 H 0.940226 0.722367 0.783359 0.036 Uiso 1 1 calc R U . . .
H9 H 0.985896 0.788433 0.870226 0.036 Uiso 1 1 calc R U . . .
C13 C 0.80899(19) 0.9283(4) 0.68737(19) 0.0279(7) Uani 1 1 d . . . . .
H10 H 0.843568 0.825791 0.677735 0.034 Uiso 1 1 calc R U . . .
H11 H 0.833963 1.030061 0.663326 0.034 Uiso 1 1 calc R U . . .
Na1 Na 0.72684(7) 0.72999(15) 0.84124(7) 0.0242(3) Uani 1 1 d . . . . .
C10 C 0.90481(19) 0.5224(4) 0.9048(2) 0.0273(7) Uani 1 1 d . . . . .
H12 H 0.960703 0.538872 0.938697 0.033 Uiso 1 1 calc R U . . .
H13 H 0.912526 0.443110 0.859566 0.033 Uiso 1 1 calc R U . . .
O3 O 0.87198(12) 0.6838(3) 0.87361(13) 0.0263(5) Uani 1 1 d . . . . .
C12 C 0.89389(19) 0.9577(4) 0.8166(2) 0.0287(7) Uani 1 1 d . . . . .
H14 H 0.892430 1.019806 0.868570 0.034 Uiso 1 1 calc R U . . .
H15 H 0.931720 1.022741 0.784678 0.034 Uiso 1 1 calc R U . . .
O4 O 0.80951(12) 0.9535(3) 0.77242(13) 0.0246(5) Uani 1 1 d . . . . .
C14 C 0.71831(19) 0.9029(4) 0.6485(2) 0.0279(7) Uani 1 1 d . . . . .
H16 H 0.682754 1.003988 0.658041 0.034 Uiso 1 1 calc R U . . .
H17 H 0.715467 0.884134 0.589180 0.034 Uiso 1 1 calc R U . . .
O5 O 0.69074(13) 0.7521(3) 0.68787(13) 0.0285(5) Uani 1 1 d . . . . .
C15 C 0.61473(18) 0.6773(4) 0.65864(19) 0.0241(7) Uani 1 1 d . . . . .
C16 C 0.55849(18) 0.7320(4) 0.59372(19) 0.0240(7) Uani 1 1 d . . . . .
H18 H 0.570514 0.831763 0.564035 0.029 Uiso 1 1 calc R U . . .
C17 C 0.48184(18) 0.6377(4) 0.57121(18) 0.0226(7) Uani 1 1 d . . . . .
N4 N 0.42696(15) 0.6918(3) 0.50494(15) 0.0231(6) Uani 1 1 d . . . . .
C18 C 0.35335(18) 0.6049(4) 0.48757(18) 0.0217(7) Uani 1 1 d . . . . .
N5 N 0.29941(15) 0.6540(3) 0.42139(16) 0.0244(6) Uani 1 1 d . . . . .
C19 C 0.22386(18) 0.5707(4) 0.41104(18) 0.0230(7) Uani 1 1 d . . . . .
C20 C 0.16391(19) 0.6145(4) 0.3410(2) 0.0242(7) Uani 1 1 d . . . . .
N6 N 0.11438(17) 0.6464(4) 0.28637(17) 0.0331(7) 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
N1 C1 1.139(4) . ?
C1 C2 1.451(4) . ?
C2 N2 1.345(4) . ?
C2 C19 1.388(4) . ?
N2 C3 1.359(4) . ?
N2 Na1 2.472(3) 2_646 ?
C3 N3 1.327(4) . ?
C3 C18 1.452(4) . ?
N3 C4 1.368(4) . ?
N3 Na1 2.540(3) 2_646 ?
C4 C5 1.405(4) . ?
C4 C17 1.418(4) . ?
C5 C6 1.364(4) . ?
C5 H1 0.9500 . ?
C6 O1 1.364(4) . ?
C6 C15 1.426(4) . ?
O1 C7 1.440(4) . ?
O1 Na1 2.413(2) . ?
C7 C8 1.489(4) . ?
C7 H2 0.9900 . ?
C7 H3 0.9900 . ?
C8 O2 1.425(4) . ?
C8 H4 0.9900 . ?
C8 H5 0.9900 . ?
O2 C9 1.436(4) . ?
O2 Na1 2.530(3) . ?
C9 C10 1.505(5) . ?
C9 H6 0.9900 . ?
C9 H7 0.9900 . ?
C11 O3 1.413(4) . ?
C11 C12 1.508(4) . ?
C11 H8 0.9900 . ?
C11 H9 0.9900 . ?
C13 O4 1.424(4) . ?
C13 C14 1.504(4) . ?
C13 H10 0.9900 . ?
C13 H11 0.9900 . ?
Na1 O3 2.314(2) . ?
Na1 O4 2.534(3) . ?
Na1 O5 2.537(3) . ?
C10 O3 1.424(4) . ?
C10 H12 0.9900 . ?
C10 H13 0.9900 . ?
C12 O4 1.434(3) . ?
C12 H14 0.9900 . ?
C12 H15 0.9900 . ?
C14 O5 1.435(4) . ?
C14 H16 0.9900 . ?
C14 H17 0.9900 . ?
O5 C15 1.364(3) . ?
C15 C16 1.368(4) . ?
C16 C17 1.422(4) . ?
C16 H18 0.9500 . ?
C17 N4 1.371(4) . ?
N4 C18 1.342(4) . ?
C18 N5 1.351(4) . ?
N5 C19 1.349(4) . ?
C19 C20 1.437(4) . ?
C20 N6 1.142(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
N1 C1 C2 178.1(3) . . ?
N2 C2 C19 123.0(3) . . ?
N2 C2 C1 117.1(3) . . ?
C19 C2 C1 119.9(3) . . ?
C2 N2 C3 115.5(3) . . ?
C2 N2 Na1 147.4(2) . 2_646 ?
C3 N2 Na1 95.62(18) . 2_646 ?
N3 C3 N2 116.0(3) . . ?
N3 C3 C18 123.0(3) . . ?
N2 C3 C18 120.9(3) . . ?
C3 N3 C4 116.4(3) . . ?
C3 N3 Na1 93.42(17) . 2_646 ?
C4 N3 Na1 147.3(2) . 2_646 ?
N3 C4 C5 118.8(3) . . ?
N3 C4 C17 121.4(3) . . ?
C5 C4 C17 119.7(3) . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H1 120.1 . . ?
C4 C5 H1 120.1 . . ?
O1 C6 C5 126.5(3) . . ?
O1 C6 C15 112.7(3) . . ?
C5 C6 C15 120.8(3) . . ?
C6 O1 C7 118.5(2) . . ?
C6 O1 Na1 116.72(19) . . ?
C7 O1 Na1 117.57(18) . . ?
O1 C7 C8 105.9(2) . . ?
O1 C7 H2 110.6 . . ?
C8 C7 H2 110.6 . . ?
O1 C7 H3 110.6 . . ?
C8 C7 H3 110.6 . . ?
H2 C7 H3 108.7 . . ?
O2 C8 C7 108.1(2) . . ?
O2 C8 H4 110.1 . . ?
C7 C8 H4 110.1 . . ?
O2 C8 H5 110.1 . . ?
C7 C8 H5 110.1 . . ?
H4 C8 H5 108.4 . . ?
C8 O2 C9 113.2(2) . . ?
C8 O2 Na1 110.50(18) . . ?
C9 O2 Na1 107.43(17) . . ?
O2 C9 C10 113.0(3) . . ?
O2 C9 H6 109.0 . . ?
C10 C9 H6 109.0 . . ?
O2 C9 H7 109.0 . . ?
C10 C9 H7 109.0 . . ?
H6 C9 H7 107.8 . . ?
O3 C11 C12 108.3(3) . . ?
O3 C11 H8 110.0 . . ?
C12 C11 H8 110.0 . . ?
O3 C11 H9 110.0 . . ?
C12 C11 H9 110.0 . . ?
H8 C11 H9 108.4 . . ?
O4 C13 C14 108.6(2) . . ?
O4 C13 H10 110.0 . . ?
C14 C13 H10 110.0 . . ?
O4 C13 H11 110.0 . . ?
C14 C13 H11 110.0 . . ?
H10 C13 H11 108.3 . . ?
O3 Na1 O1 110.37(9) . . ?
O3 Na1 N2 83.19(8) . 2_656 ?
O1 Na1 N2 146.33(9) . 2_656 ?
O3 Na1 O2 69.13(7) . . ?
O1 Na1 O2 66.66(8) . . ?
N2 Na1 O2 91.85(9) 2_656 . ?
O3 Na1 O4 69.73(8) . . ?
O1 Na1 O4 120.27(9) . . ?
N2 Na1 O4 93.20(9) 2_656 . ?
O2 Na1 O4 137.58(8) . . ?
O3 Na1 O5 108.93(8) . . ?
O1 Na1 O5 60.09(8) . . ?
N2 Na1 O5 146.26(9) 2_656 . ?
O2 Na1 O5 121.84(8) . . ?
O4 Na1 O5 64.00(7) . . ?
O3 Na1 N3 136.68(9) . 2_656 ?
O1 Na1 N3 109.71(9) . 2_656 ?
N2 Na1 N3 54.02(8) 2_656 2_656 ?
O2 Na1 N3 113.86(9) . 2_656 ?
O4 Na1 N3 102.93(9) . 2_656 ?
O5 Na1 N3 104.75(9) . 2_656 ?
O3 C10 C9 107.1(2) . . ?
O3 C10 H12 110.3 . . ?
C9 C10 H12 110.3 . . ?
O3 C10 H13 110.3 . . ?
C9 C10 H13 110.3 . . ?
H12 C10 H13 108.6 . . ?
C11 O3 C10 113.6(2) . . ?
C11 O3 Na1 120.26(18) . . ?
C10 O3 Na1 121.44(18) . . ?
O4 C12 C11 112.8(3) . . ?
O4 C12 H14 109.0 . . ?
C11 C12 H14 109.0 . . ?
O4 C12 H15 109.0 . . ?
C11 C12 H15 109.0 . . ?
H14 C12 H15 107.8 . . ?
C13 O4 C12 112.9(2) . . ?
C13 O4 Na1 114.78(17) . . ?
C12 O4 Na1 106.66(18) . . ?
O5 C14 C13 104.1(3) . . ?
O5 C14 H16 110.9 . . ?
C13 C14 H16 110.9 . . ?
O5 C14 H17 110.9 . . ?
C13 C14 H17 110.9 . . ?
H16 C14 H17 109.0 . . ?
C15 O5 C14 119.5(2) . . ?
C15 O5 Na1 113.30(18) . . ?
C14 O5 Na1 118.06(18) . . ?
O5 C15 C16 126.6(3) . . ?
O5 C15 C6 112.8(3) . . ?
C16 C15 C6 120.6(3) . . ?
C15 C16 C17 119.2(3) . . ?
C15 C16 H18 120.4 . . ?
C17 C16 H18 120.4 . . ?
N4 C17 C4 121.7(3) . . ?
N4 C17 C16 118.6(3) . . ?
C4 C17 C16 119.7(3) . . ?
C18 N4 C17 117.1(3) . . ?
N4 C18 N5 117.8(3) . . ?
N4 C18 C3 120.2(3) . . ?
N5 C18 C3 122.0(3) . . ?
C19 N5 C18 114.8(3) . . ?
N5 C19 C2 123.6(3) . . ?
N5 C19 C20 117.7(3) . . ?
C2 C19 C20 118.7(3) . . ?
N6 C20 C19 177.8(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
C19 C2 N2 C3 2.3(4) . . . . ?
C1 C2 N2 C3 -176.2(3) . . . . ?
C19 C2 N2 Na1 163.3(3) . . . 2_646 ?
C1 C2 N2 Na1 -15.3(5) . . . 2_646 ?
C2 N2 C3 N3 179.6(3) . . . . ?
Na1 N2 C3 N3 9.8(3) 2_646 . . . ?
C2 N2 C3 C18 2.3(4) . . . . ?
Na1 N2 C3 C18 -167.5(2) 2_646 . . . ?
N2 C3 N3 C4 -175.7(3) . . . . ?
C18 C3 N3 C4 1.6(4) . . . . ?
N2 C3 N3 Na1 -9.5(3) . . . 2_646 ?
C18 C3 N3 Na1 167.8(2) . . . 2_646 ?
C3 N3 C4 C5 -179.3(3) . . . . ?
Na1 N3 C4 C5 27.0(5) 2_646 . . . ?
C3 N3 C4 C17 1.8(4) . . . . ?
Na1 N3 C4 C17 -151.9(3) 2_646 . . . ?
N3 C4 C5 C6 -177.4(3) . . . . ?
C17 C4 C5 C6 1.6(4) . . . . ?
C4 C5 C6 O1 -179.5(3) . . . . ?
C4 C5 C6 C15 1.9(5) . . . . ?
C5 C6 O1 C7 11.1(5) . . . . ?
C15 C6 O1 C7 -170.3(3) . . . . ?
C5 C6 O1 Na1 -138.6(3) . . . . ?
C15 C6 O1 Na1 40.1(3) . . . . ?
C6 O1 C7 C8 167.3(3) . . . . ?
Na1 O1 C7 C8 -43.3(3) . . . . ?
O1 C7 C8 O2 61.8(3) . . . . ?
C7 C8 O2 C9 -171.8(2) . . . . ?
C7 C8 O2 Na1 -51.3(3) . . . . ?
C8 O2 C9 C10 76.6(3) . . . . ?
Na1 O2 C9 C10 -45.7(3) . . . . ?
O2 C9 C10 O3 52.5(3) . . . . ?
C12 C11 O3 C10 -171.0(3) . . . . ?
C12 C11 O3 Na1 33.0(3) . . . . ?
C9 C10 O3 C11 171.4(3) . . . . ?
C9 C10 O3 Na1 -32.9(3) . . . . ?
O3 C11 C12 O4 -53.4(4) . . . . ?
C14 C13 O4 C12 172.7(2) . . . . ?
C14 C13 O4 Na1 50.2(3) . . . . ?
C11 C12 O4 C13 -81.2(3) . . . . ?
C11 C12 O4 Na1 45.8(3) . . . . ?
O4 C13 C14 O5 -60.3(3) . . . . ?
C13 C14 O5 C15 -170.4(3) . . . . ?
C13 C14 O5 Na1 44.8(3) . . . . ?
C14 O5 C15 C16 -0.7(5) . . . . ?
Na1 O5 C15 C16 145.6(3) . . . . ?
C14 O5 C15 C6 179.1(3) . . . . ?
Na1 O5 C15 C6 -34.6(3) . . . . ?
O1 C6 C15 O5 -1.3(4) . . . . ?
C5 C6 C15 O5 177.5(3) . . . . ?
O1 C6 C15 C16 178.5(3) . . . . ?
C5 C6 C15 C16 -2.7(5) . . . . ?
O5 C15 C16 C17 179.8(3) . . . . ?
C6 C15 C16 C17 0.0(5) . . . . ?
N3 C4 C17 N4 -3.3(4) . . . . ?
C5 C4 C17 N4 177.8(3) . . . . ?
N3 C4 C17 C16 174.7(3) . . . . ?
C5 C4 C17 C16 -4.2(4) . . . . ?
C15 C16 C17 N4 -178.6(3) . . . . ?
C15 C16 C17 C4 3.4(4) . . . . ?
C4 C17 N4 C18 1.0(4) . . . . ?
C16 C17 N4 C18 -177.0(3) . . . . ?
C17 N4 C18 N5 -178.5(3) . . . . ?
C17 N4 C18 C3 2.3(4) . . . . ?
N3 C3 C18 N4 -3.9(4) . . . . ?
N2 C3 C18 N4 173.3(3) . . . . ?
N3 C3 C18 N5 177.0(3) . . . . ?
N2 C3 C18 N5 -5.8(4) . . . . ?
N4 C18 N5 C19 -175.0(3) . . . . ?
C3 C18 N5 C19 4.1(4) . . . . ?
C18 N5 C19 C2 0.5(4) . . . . ?
C18 N5 C19 C20 -179.0(3) . . . . ?
N2 C2 C19 N5 -4.0(5) . . . . ?
C1 C2 C19 N5 174.5(3) . . . . ?
N2 C2 C19 C20 175.4(3) . . . . ?
C1 C2 C19 C20 -6.1(4) . . . . ?

_refine_diff_density_max         1.048
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.071


_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_diffrn_radiation_source         ?
_diffrn_radiation_monochromator  ?
_chemical_absolute_configuration ?
