# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_40409m
_database_code_depnum_ccdc_archive 'CCDC 1420539'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H11 N3 O3'
_chemical_formula_sum            'C14 H11 N3 O3'
_chemical_formula_weight         269.26

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   10.342(6)
_cell_length_b                   6.841(4)
_cell_length_c                   17.218(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.267(15)
_cell_angle_gamma                90.00
_cell_volume                     1190.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1143
_cell_measurement_theta_min      25.5
_cell_measurement_theta_max      68.1

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8051
_exptl_absorpt_correction_T_max  0.9910
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7902
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         6.99
_diffrn_reflns_theta_max         65.97
_reflns_number_total             2041
_reflns_number_gt                1783
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1179P)²+0.2854P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2041
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1682
_refine_ls_wR_factor_gt          0.1592
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.88915(15) 0.1899(2) 0.54089(9) 0.0231(4) Uani 1 1 d . . .
H1 H 0.9717 0.2299 0.5552 0.028 Uiso 1 1 calc R . .
N2 N 1.26167(16) 0.2399(3) 0.28064(10) 0.0324(5) Uani 1 1 d . . .
H2 H 1.2232 0.1658 0.2406 0.039 Uiso 1 1 calc R . .
N3 N 0.74727(16) 0.2269(2) 0.17301(9) 0.0252(4) Uani 1 1 d . . .
O1 O 1.08357(12) 0.29067(19) 0.47143(7) 0.0254(4) Uani 1 1 d . . .
H3 H 1.1623 0.2690 0.4685 0.038 Uiso 1 1 calc R . .
O2 O 0.62723(13) 0.2313(2) 0.16959(8) 0.0302(4) Uani 1 1 d . . .
O3 O 0.79684(14) 0.2059(2) 0.11454(8) 0.0346(4) Uani 1 1 d . . .
C1 C 0.81537(18) 0.1195(3) 0.59110(11) 0.0267(5) Uani 1 1 d . . .
H4 H 0.8442 0.1046 0.6470 0.032 Uiso 1 1 calc R . .
C2 C 0.69176(18) 0.0736(3) 0.54740(11) 0.0293(5) Uani 1 1 d . . .
H5 H 0.6200 0.0218 0.5673 0.035 Uiso 1 1 calc R . .
C3 C 0.69162(18) 0.1179(3) 0.46733(11) 0.0283(5) Uani 1 1 d . . .
H6 H 0.6194 0.1016 0.4234 0.034 Uiso 1 1 calc R . .
C4 C 0.81559(18) 0.1892(3) 0.46429(11) 0.0231(5) Uani 1 1 d . . .
C5 C 0.86922(18) 0.2360(3) 0.39374(11) 0.0215(5) Uani 1 1 d . . .
C6 C 1.00437(18) 0.2786(3) 0.39780(11) 0.0223(4) Uani 1 1 d . . .
C7 C 1.05499(18) 0.2996(3) 0.32853(11) 0.0225(4) Uani 1 1 d . . .
C8 C 0.96953(19) 0.2823(3) 0.25405(11) 0.0235(4) Uani 1 1 d . . .
H7 H 1.0019 0.2943 0.2066 0.028 Uiso 1 1 calc R . .
C9 C 0.83663(18) 0.2474(3) 0.25111(11) 0.0234(5) Uani 1 1 d . . .
C10 C 0.78531(18) 0.2269(3) 0.31847(11) 0.0232(5) Uani 1 1 d . . .
H8 H 0.6931 0.2066 0.3137 0.028 Uiso 1 1 calc R . .
C11 C 1.19941(18) 0.3291(3) 0.33405(10) 0.0239(4) Uani 1 1 d . . .
C12 C 1.29049(17) 0.4311(3) 0.38787(11) 0.0279(5) Uani 1 1 d . . .
H9 H 1.2749 0.5048 0.4317 0.034 Uiso 1 1 calc R . .
C13 C 1.41397(19) 0.4043(4) 0.36473(14) 0.0419(6) Uani 1 1 d . . .
H10 H 1.4962 0.4600 0.3902 0.050 Uiso 1 1 calc R . .
C14 C 1.3935(2) 0.2853(4) 0.30008(14) 0.0407(6) Uani 1 1 d . . .
H11 H 1.4593 0.2414 0.2731 0.049 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.357(2) . ?
N1 C4 1.375(2) . ?
N1 H1 0.8800 . ?
N2 C14 1.369(3) . ?
N2 C11 1.373(3) . ?
N2 H2 0.8800 . ?
N3 O3 1.231(2) . ?
N3 O2 1.231(2) . ?
N3 C9 1.468(2) . ?
O1 C6 1.358(2) . ?
O1 H3 0.8400 . ?
C1 C2 1.375(3) . ?
C1 H4 0.9500 . ?
C2 C3 1.411(3) . ?
C2 H5 0.9500 . ?
C3 C4 1.383(3) . ?
C3 H6 0.9500 . ?
C4 C5 1.474(3) . ?
C5 C10 1.400(3) . ?
C5 C6 1.415(3) . ?
C6 C7 1.408(3) . ?
C7 C8 1.399(3) . ?
C7 C11 1.490(3) . ?
C8 C9 1.385(3) . ?
C8 H7 0.9500 . ?
C9 C10 1.381(3) . ?
C10 H8 0.9500 . ?
C11 C12 1.364(3) . ?
C12 C13 1.428(3) . ?
C12 H9 0.9500 . ?
C13 C14 1.359(4) . ?
C13 H10 0.9500 . ?
C14 H11 0.9500 . ?

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 N1 C4 109.78(16) . . ?
C1 N1 H1 125.1 . . ?
C4 N1 H1 125.1 . . ?
C14 N2 C11 108.66(19) . . ?
C14 N2 H2 125.7 . . ?
C11 N2 H2 125.7 . . ?
O3 N3 O2 123.68(16) . . ?
O3 N3 C9 118.02(16) . . ?
O2 N3 C9 118.30(16) . . ?
C6 O1 H3 109.5 . . ?
N1 C1 C2 108.40(16) . . ?
N1 C1 H4 125.8 . . ?
C2 C1 H4 125.8 . . ?
C1 C2 C3 107.05(17) . . ?
C1 C2 H5 126.5 . . ?
C3 C2 H5 126.5 . . ?
C4 C3 C2 107.71(17) . . ?
C4 C3 H6 126.1 . . ?
C2 C3 H6 126.1 . . ?
N1 C4 C3 107.05(17) . . ?
N1 C4 C5 124.14(17) . . ?
C3 C4 C5 128.46(18) . . ?
C10 C5 C6 117.81(18) . . ?
C10 C5 C4 119.06(17) . . ?
C6 C5 C4 123.02(17) . . ?
O1 C6 C7 121.71(17) . . ?
O1 C6 C5 116.89(17) . . ?
C7 C6 C5 121.36(17) . . ?
C8 C7 C6 119.44(17) . . ?
C8 C7 C11 119.95(16) . . ?
C6 C7 C11 120.52(16) . . ?
C9 C8 C7 118.47(17) . . ?
C9 C8 H7 120.8 . . ?
C7 C8 H7 120.8 . . ?
C10 C9 C8 122.82(18) . . ?
C10 C9 N3 118.69(18) . . ?
C8 C9 N3 118.47(17) . . ?
C9 C10 C5 119.98(18) . . ?
C9 C10 H8 120.0 . . ?
C5 C10 H8 120.0 . . ?
C12 C11 N2 109.14(17) . . ?
C12 C11 C7 130.59(17) . . ?
N2 C11 C7 120.23(17) . . ?
C11 C12 C13 105.91(19) . . ?
C11 C12 H9 127.0 . . ?
C13 C12 H9 127.0 . . ?
C14 C13 C12 108.23(18) . . ?
C14 C13 H10 125.9 . . ?
C12 C13 H10 125.9 . . ?
C13 C14 N2 108.0(2) . . ?
C13 C14 H11 126.0 . . ?
N2 C14 H11 126.0 . . ?

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
C4 N1 C1 C2 -0.5(2) . . . . ?
N1 C1 C2 C3 0.2(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C1 N1 C4 C3 0.6(2) . . . . ?
C1 N1 C4 C5 -173.13(18) . . . . ?
C2 C3 C4 N1 -0.5(2) . . . . ?
C2 C3 C4 C5 172.90(19) . . . . ?
N1 C4 C5 C10 178.81(16) . . . . ?
C3 C4 C5 C10 6.4(3) . . . . ?
N1 C4 C5 C6 2.8(3) . . . . ?
C3 C4 C5 C6 -169.6(2) . . . . ?
C10 C5 C6 O1 178.69(15) . . . . ?
C4 C5 C6 O1 -5.2(3) . . . . ?
C10 C5 C6 C7 -3.8(3) . . . . ?
C4 C5 C6 C7 172.31(17) . . . . ?
O1 C6 C7 C8 178.84(16) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
O1 C6 C7 C11 2.2(3) . . . . ?
C5 C6 C7 C11 -175.23(17) . . . . ?
C6 C7 C8 C9 0.8(3) . . . . ?
C11 C7 C8 C9 177.52(17) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C7 C8 C9 N3 -179.27(16) . . . . ?
O3 N3 C9 C10 -165.58(17) . . . . ?
O2 N3 C9 C10 14.3(2) . . . . ?
O3 N3 C9 C8 13.1(2) . . . . ?
O2 N3 C9 C8 -167.10(17) . . . . ?
C8 C9 C10 C5 -1.7(3) . . . . ?
N3 C9 C10 C5 176.83(15) . . . . ?
C6 C5 C10 C9 3.9(3) . . . . ?
C4 C5 C10 C9 -172.36(17) . . . . ?
C14 N2 C11 C12 -0.2(2) . . . . ?
C14 N2 C11 C7 -178.12(17) . . . . ?
C8 C7 C11 C12 146.9(2) . . . . ?
C6 C7 C11 C12 -36.4(3) . . . . ?
C8 C7 C11 N2 -35.7(3) . . . . ?
C6 C7 C11 N2 140.95(18) . . . . ?
N2 C11 C12 C13 1.0(2) . . . . ?
C7 C11 C12 C13 178.62(19) . . . . ?
C11 C12 C13 C14 -1.4(2) . . . . ?
C12 C13 C14 N2 1.3(2) . . . . ?
C11 N2 C14 C13 -0.7(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
N1 H1 O1 0.88 2.07 2.640(2) 121.3 .
N1 H1 O2 0.88 2.28 2.991(2) 138.0 4_666

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        65.97
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_40418m
_database_code_depnum_ccdc_archive 'CCDC 1420540'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 N3 O3, C16 H36 N'
_chemical_formula_sum            'C30 H46 N4 O3'
_chemical_formula_weight         510.71

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   18.1094(17)
_cell_length_b                   8.5397(8)
_cell_length_c                   19.1583(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.390(5)
_cell_angle_gamma                90.00
_cell_volume                     2856.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    5816
_cell_measurement_theta_min      4.8
_cell_measurement_theta_max      68.1

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9092
_exptl_absorpt_correction_T_max  0.9940
_exptl_absorpt_process_details   
; Higashi, T. (1995). Program for 
 Absorption Correction.
 Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28318
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_sigmaI/netI    0.0772
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.79
_diffrn_reflns_theta_max         63.00
_reflns_number_total             4566
_reflns_number_gt                2115
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4566
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1500
_refine_ls_R_factor_gt           0.0853
_refine_ls_wR_factor_ref         0.2749
_refine_ls_wR_factor_gt          0.2005
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16751(15) 0.6278(3) 0.30037(15) 0.0629(8) Uani 1 1 d . . .
O2 O 0.29841(16) 0.9192(3) 0.06053(15) 0.0685(9) Uani 1 1 d . . .
O3 O 0.20077(18) 0.7920(4) -0.00730(17) 0.0750(9) Uani 1 1 d . . .
N1 N 0.3023(2) 0.7321(4) 0.38200(19) 0.0599(10) Uani 1 1 d . . .
H1 H 0.2594 0.6923 0.3874 0.072 Uiso 1 1 calc R . .
N2 N 0.03512(19) 0.5091(4) 0.21744(18) 0.0620(10) Uani 1 1 d . . .
H2 H 0.0513 0.5468 0.2616 0.074 Uiso 1 1 calc R . .
N3 N 0.2420(2) 0.8301(4) 0.0540(2) 0.0655(10) Uani 1 1 d . . .
N4 N -0.25078(18) 0.7251(4) 0.08738(18) 0.0584(9) Uani 1 1 d . . .
C1 C 0.3660(3) 0.7600(5) 0.4370(3) 0.0648(12) Uani 1 1 d . . .
H3 H 0.3717 0.7392 0.4869 0.078 Uiso 1 1 calc R . .
C2 C 0.4207(3) 0.8239(5) 0.4075(3) 0.0649(12) Uani 1 1 d . . .
H4 H 0.4708 0.8557 0.4332 0.078 Uiso 1 1 calc R . .
C3 C 0.3886(3) 0.8336(5) 0.3316(2) 0.0640(12) Uani 1 1 d . . .
H5 H 0.4133 0.8731 0.2972 0.077 Uiso 1 1 calc R . .
C4 C 0.3147(2) 0.7750(4) 0.3166(2) 0.0576(11) Uani 1 1 d . . .
C5 C 0.2239(2) 0.7721(5) 0.1176(2) 0.0589(11) Uani 1 1 d . . .
C6 C 0.2746(2) 0.8019(4) 0.1847(2) 0.0573(11) Uani 1 1 d . . .
H6 H 0.3204 0.8588 0.1876 0.069 Uiso 1 1 calc R . .
C7 C 0.2585(2) 0.7491(4) 0.2467(2) 0.0557(11) Uani 1 1 d . . .
C8 C 0.1871(2) 0.6689(4) 0.2435(3) 0.0597(11) Uani 1 1 d . . .
C9 C 0.1376(2) 0.6325(4) 0.1714(2) 0.0574(11) Uani 1 1 d . . .
C10 C 0.1569(2) 0.6877(4) 0.1109(2) 0.0573(11) Uani 1 1 d . . .
H7 H 0.1240 0.6678 0.0642 0.069 Uiso 1 1 calc R . .
C11 C 0.0692(2) 0.5380(5) 0.1621(2) 0.0592(11) Uani 1 1 d . . .
C12 C 0.0267(2) 0.4565(5) 0.1027(2) 0.0646(12) Uani 1 1 d . . .
H8 H 0.0366 0.4527 0.0564 0.078 Uiso 1 1 calc R . .
C13 C -0.0343(2) 0.3790(5) 0.1226(3) 0.0643(12) Uani 1 1 d . . .
H9 H -0.0727 0.3152 0.0923 0.077 Uiso 1 1 calc R . .
C14 C -0.0269(2) 0.4144(5) 0.1942(3) 0.0638(12) Uani 1 1 d . . .
H10 H -0.0594 0.3789 0.2224 0.077 Uiso 1 1 calc R . .
C15 C -0.2869(2) 0.6074(4) 0.0295(2) 0.0618(11) Uani 1 1 d . . .
H11 H -0.3227 0.5419 0.0478 0.074 Uiso 1 1 calc R . .
H12 H -0.2460 0.5377 0.0219 0.074 Uiso 1 1 calc R . .
C16 C -0.3301(2) 0.6743(5) -0.0435(2) 0.0661(12) Uani 1 1 d . . .
H13 H -0.3746 0.7357 -0.0380 0.079 Uiso 1 1 calc R . .
H14 H -0.2961 0.7454 -0.0615 0.079 Uiso 1 1 calc R . .
C17 C -0.3573(3) 0.5439(5) -0.0971(2) 0.0856(15) Uani 1 1 d . . .
H15 H -0.3901 0.4724 -0.0779 0.103 Uiso 1 1 calc R . .
H16 H -0.3122 0.4833 -0.1019 0.103 Uiso 1 1 calc R . .
C18 C -0.4016(3) 0.5991(6) -0.1714(2) 0.0833(15) Uani 1 1 d . . .
H17 H -0.4190 0.5083 -0.2027 0.125 Uiso 1 1 calc R . .
H18 H -0.3686 0.6646 -0.1923 0.125 Uiso 1 1 calc R . .
H19 H -0.4461 0.6602 -0.1673 0.125 Uiso 1 1 calc R . .
C19 C -0.3106(2) 0.8375(5) 0.1012(2) 0.0600(11) Uani 1 1 d . . .
H20 H -0.2851 0.9064 0.1421 0.072 Uiso 1 1 calc R . .
H21 H -0.3283 0.9049 0.0579 0.072 Uiso 1 1 calc R . .
C20 C -0.3806(2) 0.7678(5) 0.1182(2) 0.0673(12) Uani 1 1 d . . .
H22 H -0.3651 0.7113 0.1649 0.081 Uiso 1 1 calc R . .
H23 H -0.4048 0.6915 0.0800 0.081 Uiso 1 1 calc R . .
C21 C -0.4376(2) 0.8943(5) 0.1224(3) 0.0720(13) Uani 1 1 d . . .
H24 H -0.4533 0.9491 0.0752 0.086 Uiso 1 1 calc R . .
H25 H -0.4124 0.9718 0.1594 0.086 Uiso 1 1 calc R . .
C22 C -0.5085(3) 0.8322(6) 0.1410(3) 0.0809(14) Uani 1 1 d . . .
H26 H -0.5429 0.9195 0.1434 0.121 Uiso 1 1 calc R . .
H27 H -0.4935 0.7790 0.1879 0.121 Uiso 1 1 calc R . .
H28 H -0.5348 0.7580 0.1036 0.121 Uiso 1 1 calc R . .
C23 C -0.2148(2) 0.6317(4) 0.1558(2) 0.0588(11) Uani 1 1 d . . .
H29 H -0.2564 0.5898 0.1751 0.071 Uiso 1 1 calc R . .
H30 H -0.1871 0.5413 0.1426 0.071 Uiso 1 1 calc R . .
C24 C -0.1598(2) 0.7227(5) 0.2154(2) 0.0648(12) Uani 1 1 d . . .
H31 H -0.1794 0.8306 0.2167 0.078 Uiso 1 1 calc R . .
H32 H -0.1095 0.7294 0.2044 0.078 Uiso 1 1 calc R . .
C25 C -0.1494(2) 0.6459(5) 0.2900(2) 0.0642(12) Uani 1 1 d . . .
H33 H -0.1465 0.5309 0.2848 0.077 Uiso 1 1 calc R . .
H34 H -0.1004 0.6815 0.3227 0.077 Uiso 1 1 calc R . .
C26 C -0.2142(3) 0.6846(5) 0.3239(3) 0.0747(13) Uani 1 1 d . . .
H35 H -0.2048 0.6332 0.3712 0.112 Uiso 1 1 calc R . .
H36 H -0.2628 0.6473 0.2923 0.112 Uiso 1 1 calc R . .
H37 H -0.2167 0.7982 0.3301 0.112 Uiso 1 1 calc R . .
C27 C -0.1922(2) 0.8250(5) 0.0647(2) 0.0588(11) Uani 1 1 d . . .
H38 H -0.1686 0.8966 0.1051 0.071 Uiso 1 1 calc R . .
H39 H -0.2193 0.8905 0.0231 0.071 Uiso 1 1 calc R . .
C28 C -0.1285(2) 0.7371(5) 0.0435(2) 0.0622(12) Uani 1 1 d . . .
H40 H -0.1503 0.6756 -0.0010 0.075 Uiso 1 1 calc R . .
H41 H -0.1038 0.6633 0.0826 0.075 Uiso 1 1 calc R . .
C29 C -0.0691(2) 0.8516(5) 0.0303(2) 0.0647(12) Uani 1 1 d . . .
H42 H -0.0952 0.9307 -0.0055 0.078 Uiso 1 1 calc R . .
H43 H -0.0326 0.7939 0.0093 0.078 Uiso 1 1 calc R . .
C30 C -0.0242(2) 0.9357(5) 0.0993(2) 0.0723(13) Uani 1 1 d . . .
H44 H 0.0128 1.0079 0.0875 0.108 Uiso 1 1 calc R . .
H45 H 0.0031 0.8583 0.1346 0.108 Uiso 1 1 calc R . .
H46 H -0.0597 0.9946 0.1200 0.108 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.281(5) . ?
O2 N3 1.254(4) . ?
O3 N3 1.255(4) . ?
N1 C1 1.361(5) . ?
N1 C4 1.380(5) . ?
N1 H1 0.8800 . ?
N2 C14 1.359(5) . ?
N2 C11 1.382(5) . ?
N2 H2 0.8800 . ?
N3 C5 1.432(5) . ?
N4 C15 1.510(5) . ?
N4 C27 1.512(5) . ?
N4 C19 1.523(5) . ?
N4 C23 1.525(4) . ?
C1 C2 1.378(6) . ?
C1 H3 0.9500 . ?
C2 C3 1.418(6) . ?
C2 H4 0.9500 . ?
C3 C4 1.386(6) . ?
C3 H5 0.9500 . ?
C4 C7 1.468(5) . ?
C5 C10 1.387(5) . ?
C5 C6 1.390(6) . ?
C6 C7 1.373(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.450(5) . ?
C8 C9 1.466(6) . ?
C9 C10 1.379(5) . ?
C9 C11 1.450(5) . ?
C10 H7 0.9500 . ?
C11 C12 1.381(5) . ?
C12 C13 1.424(5) . ?
C12 H8 0.9500 . ?
C13 C14 1.376(6) . ?
C13 H9 0.9500 . ?
C14 H10 0.9500 . ?
C15 C16 1.521(5) . ?
C15 H11 0.9900 . ?
C15 H12 0.9900 . ?
C16 C17 1.506(5) . ?
C16 H13 0.9900 . ?
C16 H14 0.9900 . ?
C17 C18 1.511(5) . ?
C17 H15 0.9900 . ?
C17 H16 0.9900 . ?
C18 H17 0.9800 . ?
C18 H18 0.9800 . ?
C18 H19 0.9800 . ?
C19 C20 1.511(5) . ?
C19 H20 0.9900 . ?
C19 H21 0.9900 . ?
C20 C21 1.511(5) . ?
C20 H22 0.9900 . ?
C20 H23 0.9900 . ?
C21 C22 1.515(6) . ?
C21 H24 0.9900 . ?
C21 H25 0.9900 . ?
C22 H26 0.9800 . ?
C22 H27 0.9800 . ?
C22 H28 0.9800 . ?
C23 C24 1.514(5) . ?
C23 H29 0.9900 . ?
C23 H30 0.9900 . ?
C24 C25 1.538(5) . ?
C24 H31 0.9900 . ?
C24 H32 0.9900 . ?
C25 C26 1.520(6) . ?
C25 H33 0.9900 . ?
C25 H34 0.9900 . ?
C26 H35 0.9800 . ?
C26 H36 0.9800 . ?
C26 H37 0.9800 . ?
C27 C28 1.520(6) . ?
C27 H38 0.9900 . ?
C27 H39 0.9900 . ?
C28 C29 1.524(5) . ?
C28 H40 0.9900 . ?
C28 H41 0.9900 . ?
C29 C30 1.535(5) . ?
C29 H42 0.9900 . ?
C29 H43 0.9900 . ?
C30 H44 0.9800 . ?
C30 H45 0.9800 . ?
C30 H46 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
C1 N1 C4 110.4(4) . . ?
C1 N1 H1 124.8 . . ?
C4 N1 H1 124.8 . . ?
C14 N2 C11 110.6(4) . . ?
C14 N2 H2 124.7 . . ?
C11 N2 H2 124.7 . . ?
O2 N3 O3 121.2(4) . . ?
O2 N3 C5 119.3(4) . . ?
O3 N3 C5 119.5(4) . . ?
C15 N4 C27 111.4(3) . . ?
C15 N4 C19 111.0(3) . . ?
C27 N4 C19 106.3(3) . . ?
C15 N4 C23 106.6(3) . . ?
C27 N4 C23 111.7(3) . . ?
C19 N4 C23 110.0(3) . . ?
N1 C1 C2 107.7(4) . . ?
N1 C1 H3 126.1 . . ?
C2 C1 H3 126.1 . . ?
C1 C2 C3 107.5(4) . . ?
C1 C2 H4 126.2 . . ?
C3 C2 H4 126.2 . . ?
C4 C3 C2 107.5(4) . . ?
C4 C3 H5 126.2 . . ?
C2 C3 H5 126.2 . . ?
N1 C4 C3 106.8(4) . . ?
N1 C4 C7 123.2(4) . . ?
C3 C4 C7 129.9(4) . . ?
C10 C5 C6 121.8(4) . . ?
C10 C5 N3 119.6(4) . . ?
C6 C5 N3 118.6(4) . . ?
C7 C6 C5 120.0(4) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C8 120.7(4) . . ?
C6 C7 C4 119.0(4) . . ?
C8 C7 C4 120.3(4) . . ?
O1 C8 C7 122.5(4) . . ?
O1 C8 C9 120.4(4) . . ?
C7 C8 C9 117.1(4) . . ?
C10 C9 C11 119.1(4) . . ?
C10 C9 C8 119.4(4) . . ?
C11 C9 C8 121.5(4) . . ?
C9 C10 C5 120.7(4) . . ?
C9 C10 H7 119.6 . . ?
C5 C10 H7 119.6 . . ?
C12 C11 N2 106.2(4) . . ?
C12 C11 C9 130.7(4) . . ?
N2 C11 C9 123.1(4) . . ?
C11 C12 C13 108.3(4) . . ?
C11 C12 H8 125.8 . . ?
C13 C12 H8 125.8 . . ?
C14 C13 C12 106.7(4) . . ?
C14 C13 H9 126.6 . . ?
C12 C13 H9 126.6 . . ?
N2 C14 C13 108.1(4) . . ?
N2 C14 H10 125.9 . . ?
C13 C14 H10 125.9 . . ?
N4 C15 C16 116.2(3) . . ?
N4 C15 H11 108.2 . . ?
C16 C15 H11 108.2 . . ?
N4 C15 H12 108.2 . . ?
C16 C15 H12 108.2 . . ?
H11 C15 H12 107.4 . . ?
C17 C16 C15 110.2(3) . . ?
C17 C16 H13 109.6 . . ?
C15 C16 H13 109.6 . . ?
C17 C16 H14 109.6 . . ?
C15 C16 H14 109.6 . . ?
H13 C16 H14 108.1 . . ?
C16 C17 C18 114.1(4) . . ?
C16 C17 H15 108.7 . . ?
C18 C17 H15 108.7 . . ?
C16 C17 H16 108.7 . . ?
C18 C17 H16 108.7 . . ?
H15 C17 H16 107.6 . . ?
C17 C18 H17 109.5 . . ?
C17 C18 H18 109.5 . . ?
H17 C18 H18 109.5 . . ?
C17 C18 H19 109.5 . . ?
H17 C18 H19 109.5 . . ?
H18 C18 H19 109.5 . . ?
C20 C19 N4 117.7(3) . . ?
C20 C19 H20 107.9 . . ?
N4 C19 H20 107.9 . . ?
C20 C19 H21 107.9 . . ?
N4 C19 H21 107.9 . . ?
H20 C19 H21 107.2 . . ?
C19 C20 C21 110.7(4) . . ?
C19 C20 H22 109.5 . . ?
C21 C20 H22 109.5 . . ?
C19 C20 H23 109.5 . . ?
C21 C20 H23 109.5 . . ?
H22 C20 H23 108.1 . . ?
C20 C21 C22 113.3(4) . . ?
C20 C21 H24 108.9 . . ?
C22 C21 H24 108.9 . . ?
C20 C21 H25 108.9 . . ?
C22 C21 H25 108.9 . . ?
H24 C21 H25 107.7 . . ?
C21 C22 H26 109.5 . . ?
C21 C22 H27 109.5 . . ?
H26 C22 H27 109.5 . . ?
C21 C22 H28 109.5 . . ?
H26 C22 H28 109.5 . . ?
H27 C22 H28 109.5 . . ?
C24 C23 N4 115.2(3) . . ?
C24 C23 H29 108.5 . . ?
N4 C23 H29 108.5 . . ?
C24 C23 H30 108.5 . . ?
N4 C23 H30 108.5 . . ?
H29 C23 H30 107.5 . . ?
C23 C24 C25 112.1(3) . . ?
C23 C24 H31 109.2 . . ?
C25 C24 H31 109.2 . . ?
C23 C24 H32 109.2 . . ?
C25 C24 H32 109.2 . . ?
H31 C24 H32 107.9 . . ?
C26 C25 C24 112.7(4) . . ?
C26 C25 H33 109.0 . . ?
C24 C25 H33 109.0 . . ?
C26 C25 H34 109.0 . . ?
C24 C25 H34 109.0 . . ?
H33 C25 H34 107.8 . . ?
C25 C26 H35 109.5 . . ?
C25 C26 H36 109.5 . . ?
H35 C26 H36 109.5 . . ?
C25 C26 H37 109.5 . . ?
H35 C26 H37 109.5 . . ?
H36 C26 H37 109.5 . . ?
N4 C27 C28 116.0(3) . . ?
N4 C27 H38 108.3 . . ?
C28 C27 H38 108.3 . . ?
N4 C27 H39 108.3 . . ?
C28 C27 H39 108.3 . . ?
H38 C27 H39 107.4 . . ?
C27 C28 C29 110.3(3) . . ?
C27 C28 H40 109.6 . . ?
C29 C28 H40 109.6 . . ?
C27 C28 H41 109.6 . . ?
C29 C28 H41 109.6 . . ?
H40 C28 H41 108.1 . . ?
C28 C29 C30 113.2(4) . . ?
C28 C29 H42 108.9 . . ?
C30 C29 H42 108.9 . . ?
C28 C29 H43 108.9 . . ?
C30 C29 H43 108.9 . . ?
H42 C29 H43 107.7 . . ?
C29 C30 H44 109.5 . . ?
C29 C30 H45 109.5 . . ?
H44 C30 H45 109.5 . . ?
C29 C30 H46 109.5 . . ?
H44 C30 H46 109.5 . . ?
H45 C30 H46 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 0.7(5) . . . . ?
N1 C1 C2 C3 -0.4(5) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C1 N1 C4 C3 -0.7(4) . . . . ?
C1 N1 C4 C7 175.7(3) . . . . ?
C2 C3 C4 N1 0.4(4) . . . . ?
C2 C3 C4 C7 -175.7(4) . . . . ?
O2 N3 C5 C10 172.9(3) . . . . ?
O3 N3 C5 C10 -6.5(6) . . . . ?
O2 N3 C5 C6 -7.3(6) . . . . ?
O3 N3 C5 C6 173.3(4) . . . . ?
C10 C5 C6 C7 -0.8(6) . . . . ?
N3 C5 C6 C7 179.4(3) . . . . ?
C5 C6 C7 C8 -3.1(6) . . . . ?
C5 C6 C7 C4 176.9(4) . . . . ?
N1 C4 C7 C6 177.2(3) . . . . ?
C3 C4 C7 C6 -7.3(7) . . . . ?
N1 C4 C7 C8 -2.8(6) . . . . ?
C3 C4 C7 C8 172.8(4) . . . . ?
C6 C7 C8 O1 -174.9(4) . . . . ?
C4 C7 C8 O1 5.1(6) . . . . ?
C6 C7 C8 C9 6.5(6) . . . . ?
C4 C7 C8 C9 -173.6(3) . . . . ?
O1 C8 C9 C10 175.3(3) . . . . ?
C7 C8 C9 C10 -6.1(5) . . . . ?
O1 C8 C9 C11 -5.4(6) . . . . ?
C7 C8 C9 C11 173.3(4) . . . . ?
C11 C9 C10 C5 -176.9(4) . . . . ?
C8 C9 C10 C5 2.4(6) . . . . ?
C6 C5 C10 C9 1.2(6) . . . . ?
N3 C5 C10 C9 -179.1(4) . . . . ?
C14 N2 C11 C12 -0.6(4) . . . . ?
C14 N2 C11 C9 -178.5(3) . . . . ?
C10 C9 C11 C12 18.6(6) . . . . ?
C8 C9 C11 C12 -160.7(4) . . . . ?
C10 C9 C11 N2 -164.0(4) . . . . ?
C8 C9 C11 N2 16.7(6) . . . . ?
N2 C11 C12 C13 0.7(4) . . . . ?
C9 C11 C12 C13 178.4(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C11 N2 C14 C13 0.2(5) . . . . ?
C12 C13 C14 N2 0.2(4) . . . . ?
C27 N4 C15 C16 -60.7(5) . . . . ?
C19 N4 C15 C16 57.4(5) . . . . ?
C23 N4 C15 C16 177.2(4) . . . . ?
N4 C15 C16 C17 175.4(4) . . . . ?
C15 C16 C17 C18 179.4(4) . . . . ?
C15 N4 C19 C20 53.2(5) . . . . ?
C27 N4 C19 C20 174.4(3) . . . . ?
C23 N4 C19 C20 -64.5(4) . . . . ?
N4 C19 C20 C21 -173.9(4) . . . . ?
C19 C20 C21 C22 -178.7(4) . . . . ?
C15 N4 C23 C24 166.3(4) . . . . ?
C27 N4 C23 C24 44.4(5) . . . . ?
C19 N4 C23 C24 -73.4(4) . . . . ?
N4 C23 C24 C25 158.7(3) . . . . ?
C23 C24 C25 C26 -80.6(4) . . . . ?
C15 N4 C27 C28 -55.6(4) . . . . ?
C19 N4 C27 C28 -176.5(3) . . . . ?
C23 N4 C27 C28 63.6(4) . . . . ?
N4 C27 C28 C29 -173.5(3) . . . . ?
C27 C28 C29 C30 67.3(4) . . . . ?

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 H1 O1 0.88 2.09 2.678(4) 123.3 .
N1 H1 O3 0.88 2.52 3.161(5) 130.3 4_576
N2 H2 O1 0.88 2.15 2.698(4) 119.7 .

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        63.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_40416m
_database_code_depnum_ccdc_archive 'CCDC 1420541'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 N3 O3, C12 H28 N'
_chemical_formula_sum            'C26 H38 N4 O3'
_chemical_formula_weight         454.60

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   16.8579(5)
_cell_length_b                   8.6583(3)
_cell_length_c                   18.4879(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.4165(15)
_cell_angle_gamma                90.00
_cell_volume                     2512.18(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    13762
_cell_measurement_theta_min      4.4
_cell_measurement_theta_max      68.2

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6320
_exptl_absorpt_correction_T_max  0.9395
_exptl_absorpt_process_details   
; Higashi, T. (1995). Program for 
 Absorption Correction.
 Rigaku Corporation, Tokyo, Japan.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25534
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.88
_diffrn_reflns_theta_max         66.00
_reflns_number_total             4368
_reflns_number_gt                2571
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0520P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4368
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31136(8) 0.16551(17) 0.19609(8) 0.0424(4) Uani 1 1 d . . .
O2 O 0.16944(10) 0.39509(19) -0.14510(8) 0.0552(5) Uani 1 1 d . . .
O3 O 0.28197(10) 0.2724(2) -0.14556(9) 0.0573(5) Uani 1 1 d . . .
N1 N 0.15789(11) 0.2709(2) 0.18795(10) 0.0408(5) Uani 1 1 d . . .
H1 H 0.2041 0.2308 0.2227 0.049 Uiso 1 1 calc R . .
N2 N 0.23418(13) 0.3151(2) -0.11124(11) 0.0466(5) Uani 1 1 d . . .
N3 N 0.45833(10) 0.0388(2) 0.20185(10) 0.0398(5) Uani 1 1 d . . .
H2 H 0.4402 0.0882 0.2345 0.048 Uiso 1 1 calc R . .
N4 N 0.75752(11) 0.2538(2) 0.25417(10) 0.0398(5) Uani 1 1 d . . .
C1 C 0.08657(14) 0.3123(3) 0.20164(14) 0.0438(6) Uani 1 1 d . . .
H3 H 0.0784 0.3026 0.2496 0.053 Uiso 1 1 calc R . .
C2 C 0.02874(15) 0.3705(3) 0.13406(13) 0.0463(6) Uani 1 1 d . . .
H4 H -0.0265 0.4088 0.1267 0.056 Uiso 1 1 calc R . .
C3 C 0.06620(14) 0.3630(3) 0.07771(14) 0.0438(6) Uani 1 1 d . . .
H5 H 0.0405 0.3951 0.0251 0.053 Uiso 1 1 calc R . .
C4 C 0.14702(14) 0.3008(2) 0.11201(12) 0.0367(5) Uani 1 1 d . . .
C5 C 0.25306(14) 0.2702(3) -0.03288(12) 0.0385(6) Uani 1 1 d . . .
C6 C 0.19485(14) 0.3053(2) 0.00214(12) 0.0385(6) Uani 1 1 d . . .
H6 H 0.1433 0.3569 -0.0269 0.046 Uiso 1 1 calc R . .
C7 C 0.21119(14) 0.2659(2) 0.07859(12) 0.0354(5) Uani 1 1 d . . .
C8 C 0.29162(14) 0.1913(3) 0.12349(12) 0.0370(6) Uani 1 1 d . . .
C9 C 0.34745(13) 0.1468(3) 0.08329(12) 0.0363(6) Uani 1 1 d . . .
C10 C 0.32804(14) 0.1891(3) 0.00698(12) 0.0393(6) Uani 1 1 d . . .
H7 H 0.3658 0.1630 -0.0187 0.047 Uiso 1 1 calc R . .
C11 C 0.42325(13) 0.0518(3) 0.12246(12) 0.0381(6) Uani 1 1 d . . .
C12 C 0.46984(14) -0.0429(3) 0.09309(13) 0.0438(6) Uani 1 1 d . . .
H8 H 0.4604 -0.0576 0.0397 0.053 Uiso 1 1 calc R . .
C13 C 0.53404(14) -0.1144(3) 0.15612(14) 0.0462(6) Uani 1 1 d . . .
H9 H 0.5755 -0.1856 0.1528 0.055 Uiso 1 1 calc R . .
C14 C 0.52562(14) -0.0621(3) 0.22306(14) 0.0445(6) Uani 1 1 d . . .
H10 H 0.5601 -0.0907 0.2746 0.053 Uiso 1 1 calc R . .
C15 C 0.68662(13) 0.3568(3) 0.20228(12) 0.0411(6) Uani 1 1 d . . .
H11 H 0.6683 0.4256 0.2360 0.049 Uiso 1 1 calc R . .
H12 H 0.7106 0.4231 0.1717 0.049 Uiso 1 1 calc R . .
C16 C 0.60851(14) 0.2772(3) 0.14646(13) 0.0526(7) Uani 1 1 d . . .
H13 H 0.5796 0.2188 0.1758 0.063 Uiso 1 1 calc R . .
H14 H 0.6253 0.2034 0.1137 0.063 Uiso 1 1 calc R . .
C17 C 0.54823(14) 0.3975(3) 0.09544(13) 0.0577(7) Uani 1 1 d . . .
H15 H 0.4975 0.3462 0.0591 0.087 Uiso 1 1 calc R . .
H16 H 0.5770 0.4544 0.0662 0.087 Uiso 1 1 calc R . .
H17 H 0.5313 0.4695 0.1281 0.087 Uiso 1 1 calc R . .
C18 C 0.82851(13) 0.3627(3) 0.30059(13) 0.0445(6) Uani 1 1 d . . .
H18 H 0.8467 0.4219 0.2636 0.053 Uiso 1 1 calc R . .
H19 H 0.8047 0.4375 0.3277 0.053 Uiso 1 1 calc R . .
C19 C 0.90672(14) 0.2902(3) 0.36014(14) 0.0583(7) Uani 1 1 d . . .
H20 H 0.8909 0.2365 0.4002 0.070 Uiso 1 1 calc R . .
H21 H 0.9313 0.2133 0.3347 0.070 Uiso 1 1 calc R . .
C20 C 0.97100(17) 0.4132(3) 0.39733(17) 0.0840(10) Uani 1 1 d . . .
H22 H 1.0214 0.3665 0.4365 0.126 Uiso 1 1 calc R . .
H23 H 0.9463 0.4893 0.4223 0.126 Uiso 1 1 calc R . .
H24 H 0.9874 0.4645 0.3576 0.126 Uiso 1 1 calc R . .
C21 C 0.78773(15) 0.1431(3) 0.20606(13) 0.0485(7) Uani 1 1 d . . .
H25 H 0.8321 0.0753 0.2419 0.058 Uiso 1 1 calc R . .
H26 H 0.7392 0.0765 0.1757 0.058 Uiso 1 1 calc R . .
C22 C 0.82359(17) 0.2174(3) 0.15058(15) 0.0617(8) Uani 1 1 d . . .
H27 H 0.8796 0.2643 0.1804 0.074 Uiso 1 1 calc R . .
H28 H 0.7849 0.3008 0.1214 0.074 Uiso 1 1 calc R . .
C23 C 0.83402(17) 0.1003(3) 0.09398(15) 0.0701(8) Uani 1 1 d . . .
H29 H 0.8574 0.1514 0.0588 0.105 Uiso 1 1 calc R . .
H30 H 0.7784 0.0553 0.0637 0.105 Uiso 1 1 calc R . .
H31 H 0.8730 0.0185 0.1227 0.105 Uiso 1 1 calc R . .
C24 C 0.72775(14) 0.1541(3) 0.30716(13) 0.0454(6) Uani 1 1 d . . .
H32 H 0.7768 0.0930 0.3412 0.055 Uiso 1 1 calc R . .
H33 H 0.6845 0.0805 0.2746 0.055 Uiso 1 1 calc R . .
C25 C 0.68987(16) 0.2429(3) 0.35815(13) 0.0532(7) Uani 1 1 d . . .
H34 H 0.7269 0.3319 0.3823 0.064 Uiso 1 1 calc R . .
H35 H 0.6330 0.2833 0.3257 0.064 Uiso 1 1 calc R . .
C26 C 0.68149(16) 0.1390(3) 0.42130(14) 0.0602(7) Uani 1 1 d . . .
H36 H 0.6574 0.1982 0.4536 0.090 Uiso 1 1 calc R . .
H37 H 0.7378 0.0998 0.4537 0.090 Uiso 1 1 calc R . .
H38 H 0.6438 0.0521 0.3973 0.090 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.279(2) . ?
O2 N2 1.250(2) . ?
O3 N2 1.250(2) . ?
N1 C1 1.364(3) . ?
N1 C4 1.373(2) . ?
N1 H1 0.8800 . ?
N2 C5 1.419(3) . ?
N3 C14 1.371(2) . ?
N3 C11 1.372(2) . ?
N3 H2 0.8800 . ?
N4 C21 1.517(3) . ?
N4 C15 1.519(2) . ?
N4 C18 1.519(2) . ?
N4 C24 1.521(3) . ?
C1 C2 1.370(3) . ?
C1 H3 0.9500 . ?
C2 C3 1.403(3) . ?
C2 H4 0.9500 . ?
C3 C4 1.385(3) . ?
C3 H5 0.9500 . ?
C4 C7 1.460(3) . ?
C5 C6 1.392(3) . ?
C5 C10 1.398(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.457(3) . ?
C8 C9 1.448(3) . ?
C9 C10 1.377(3) . ?
C9 C11 1.469(3) . ?
C10 H7 0.9500 . ?
C11 C12 1.377(3) . ?
C12 C13 1.411(3) . ?
C12 H8 0.9500 . ?
C13 C14 1.373(3) . ?
C13 H9 0.9500 . ?
C14 H10 0.9500 . ?
C15 C16 1.510(3) . ?
C15 H11 0.9900 . ?
C15 H12 0.9900 . ?
C16 C17 1.519(3) . ?
C16 H13 0.9900 . ?
C16 H14 0.9900 . ?
C17 H15 0.9800 . ?
C17 H16 0.9800 . ?
C17 H17 0.9800 . ?
C18 C19 1.511(3) . ?
C18 H18 0.9900 . ?
C18 H19 0.9900 . ?
C19 C20 1.496(3) . ?
C19 H20 0.9900 . ?
C19 H21 0.9900 . ?
C20 H22 0.9800 . ?
C20 H23 0.9800 . ?
C20 H24 0.9800 . ?
C21 C22 1.512(3) . ?
C21 H25 0.9900 . ?
C21 H26 0.9900 . ?
C22 C23 1.513(3) . ?
C22 H27 0.9900 . ?
C22 H28 0.9900 . ?
C23 H29 0.9800 . ?
C23 H30 0.9800 . ?
C23 H31 0.9800 . ?
C24 C25 1.526(3) . ?
C24 H32 0.9900 . ?
C24 H33 0.9900 . ?
C25 C26 1.521(3) . ?
C25 H34 0.9900 . ?
C25 H35 0.9900 . ?
C26 H36 0.9800 . ?
C26 H37 0.9800 . ?
C26 H38 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
C1 N1 C4 110.04(19) . . ?
C1 N1 H1 125.0 . . ?
C4 N1 H1 125.0 . . ?
O3 N2 O2 121.08(19) . . ?
O3 N2 C5 119.4(2) . . ?
O2 N2 C5 119.5(2) . . ?
C14 N3 C11 110.27(19) . . ?
C14 N3 H2 124.9 . . ?
C11 N3 H2 124.9 . . ?
C21 N4 C15 110.86(16) . . ?
C21 N4 C18 111.08(17) . . ?
C15 N4 C18 105.56(16) . . ?
C21 N4 C24 106.23(17) . . ?
C15 N4 C24 111.78(16) . . ?
C18 N4 C24 111.42(17) . . ?
N1 C1 C2 108.0(2) . . ?
N1 C1 H3 126.0 . . ?
C2 C1 H3 126.0 . . ?
C1 C2 C3 107.3(2) . . ?
C1 C2 H4 126.4 . . ?
C3 C2 H4 126.4 . . ?
C4 C3 C2 108.2(2) . . ?
C4 C3 H5 125.9 . . ?
C2 C3 H5 125.9 . . ?
N1 C4 C3 106.5(2) . . ?
N1 C4 C7 123.44(19) . . ?
C3 C4 C7 130.1(2) . . ?
C6 C5 C10 121.3(2) . . ?
C6 C5 N2 118.8(2) . . ?
C10 C5 N2 119.9(2) . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.3(2) . . ?
C6 C7 C4 118.7(2) . . ?
C8 C7 C4 122.00(19) . . ?
O1 C8 C9 121.6(2) . . ?
O1 C8 C7 120.4(2) . . ?
C9 C8 C7 118.01(19) . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 C11 119.5(2) . . ?
C8 C9 C11 120.49(19) . . ?
C9 C10 C5 120.3(2) . . ?
C9 C10 H7 119.8 . . ?
C5 C10 H7 119.8 . . ?
N3 C11 C12 106.7(2) . . ?
N3 C11 C9 122.0(2) . . ?
C12 C11 C9 131.1(2) . . ?
C11 C12 C13 108.1(2) . . ?
C11 C12 H8 125.9 . . ?
C13 C12 H8 125.9 . . ?
C14 C13 C12 107.4(2) . . ?
C14 C13 H9 126.3 . . ?
C12 C13 H9 126.3 . . ?
N3 C14 C13 107.4(2) . . ?
N3 C14 H10 126.3 . . ?
C13 C14 H10 126.3 . . ?
C16 C15 N4 116.90(18) . . ?
C16 C15 H11 108.1 . . ?
N4 C15 H11 108.1 . . ?
C16 C15 H12 108.1 . . ?
N4 C15 H12 108.1 . . ?
H11 C15 H12 107.3 . . ?
C15 C16 C17 109.27(19) . . ?
C15 C16 H13 109.8 . . ?
C17 C16 H13 109.8 . . ?
C15 C16 H14 109.8 . . ?
C17 C16 H14 109.8 . . ?
H13 C16 H14 108.3 . . ?
C16 C17 H15 109.5 . . ?
C16 C17 H16 109.5 . . ?
H15 C17 H16 109.5 . . ?
C16 C17 H17 109.5 . . ?
H15 C17 H17 109.5 . . ?
H16 C17 H17 109.5 . . ?
C19 C18 N4 116.85(18) . . ?
C19 C18 H18 108.1 . . ?
N4 C18 H18 108.1 . . ?
C19 C18 H19 108.1 . . ?
N4 C18 H19 108.1 . . ?
H18 C18 H19 107.3 . . ?
C20 C19 C18 109.4(2) . . ?
C20 C19 H20 109.8 . . ?
C18 C19 H20 109.8 . . ?
C20 C19 H21 109.8 . . ?
C18 C19 H21 109.8 . . ?
H20 C19 H21 108.2 . . ?
C19 C20 H22 109.5 . . ?
C19 C20 H23 109.5 . . ?
H22 C20 H23 109.5 . . ?
C19 C20 H24 109.5 . . ?
H22 C20 H24 109.5 . . ?
H23 C20 H24 109.5 . . ?
C22 C21 N4 115.6(2) . . ?
C22 C21 H25 108.4 . . ?
N4 C21 H25 108.4 . . ?
C22 C21 H26 108.4 . . ?
N4 C21 H26 108.4 . . ?
H25 C21 H26 107.4 . . ?
C21 C22 C23 111.1(2) . . ?
C21 C22 H27 109.4 . . ?
C23 C22 H27 109.4 . . ?
C21 C22 H28 109.4 . . ?
C23 C22 H28 109.4 . . ?
H27 C22 H28 108.0 . . ?
C22 C23 H29 109.5 . . ?
C22 C23 H30 109.5 . . ?
H29 C23 H30 109.5 . . ?
C22 C23 H31 109.5 . . ?
H29 C23 H31 109.5 . . ?
H30 C23 H31 109.5 . . ?
N4 C24 C25 115.03(19) . . ?
N4 C24 H32 108.5 . . ?
C25 C24 H32 108.5 . . ?
N4 C24 H33 108.5 . . ?
C25 C24 H33 108.5 . . ?
H32 C24 H33 107.5 . . ?
C26 C25 C24 110.7(2) . . ?
C26 C25 H34 109.5 . . ?
C24 C25 H34 109.5 . . ?
C26 C25 H35 109.5 . . ?
C24 C25 H35 109.5 . . ?
H34 C25 H35 108.1 . . ?
C25 C26 H36 109.5 . . ?
C25 C26 H37 109.5 . . ?
H36 C26 H37 109.5 . . ?
C25 C26 H38 109.5 . . ?
H36 C26 H38 109.5 . . ?
H37 C26 H38 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -0.3(3) . . . . ?
N1 C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 N1 C4 C3 0.0(2) . . . . ?
C1 N1 C4 C7 -178.50(19) . . . . ?
C2 C3 C4 N1 0.2(2) . . . . ?
C2 C3 C4 C7 178.6(2) . . . . ?
O3 N2 C5 C6 -173.64(19) . . . . ?
O2 N2 C5 C6 5.5(3) . . . . ?
O3 N2 C5 C10 4.9(3) . . . . ?
O2 N2 C5 C10 -176.0(2) . . . . ?
C10 C5 C6 C7 2.5(3) . . . . ?
N2 C5 C6 C7 -179.00(18) . . . . ?
C5 C6 C7 C8 2.0(3) . . . . ?
C5 C6 C7 C4 -178.10(19) . . . . ?
N1 C4 C7 C6 -177.96(19) . . . . ?
C3 C4 C7 C6 3.9(3) . . . . ?
N1 C4 C7 C8 1.9(3) . . . . ?
C3 C4 C7 C8 -176.3(2) . . . . ?
C6 C7 C8 O1 174.1(2) . . . . ?
C4 C7 C8 O1 -5.8(3) . . . . ?
C6 C7 C8 C9 -6.4(3) . . . . ?
C4 C7 C8 C9 173.70(19) . . . . ?
O1 C8 C9 C10 -173.92(19) . . . . ?
C7 C8 C9 C10 6.6(3) . . . . ?
O1 C8 C9 C11 8.3(3) . . . . ?
C7 C8 C9 C11 -171.19(18) . . . . ?
C8 C9 C10 C5 -2.3(3) . . . . ?
C11 C9 C10 C5 175.50(19) . . . . ?
C6 C5 C10 C9 -2.4(3) . . . . ?
N2 C5 C10 C9 179.1(2) . . . . ?
C14 N3 C11 C12 -0.2(2) . . . . ?
C14 N3 C11 C9 177.04(18) . . . . ?
C10 C9 C11 N3 162.9(2) . . . . ?
C8 C9 C11 N3 -19.3(3) . . . . ?
C10 C9 C11 C12 -20.6(4) . . . . ?
C8 C9 C11 C12 157.2(2) . . . . ?
N3 C11 C12 C13 0.1(2) . . . . ?
C9 C11 C12 C13 -176.8(2) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C11 N3 C14 C13 0.2(2) . . . . ?
C12 C13 C14 N3 -0.1(2) . . . . ?
C21 N4 C15 C16 57.0(2) . . . . ?
C18 N4 C15 C16 177.32(19) . . . . ?
C24 N4 C15 C16 -61.4(2) . . . . ?
N4 C15 C16 C17 -175.52(19) . . . . ?
C21 N4 C18 C19 -62.2(3) . . . . ?
C15 N4 C18 C19 177.55(19) . . . . ?
C24 N4 C18 C19 56.0(3) . . . . ?
N4 C18 C19 C20 177.4(2) . . . . ?
C15 N4 C21 C22 60.5(2) . . . . ?
C18 N4 C21 C22 -56.5(2) . . . . ?
C24 N4 C21 C22 -177.86(19) . . . . ?
N4 C21 C22 C23 -167.8(2) . . . . ?
C21 N4 C24 C25 -176.84(18) . . . . ?
C15 N4 C24 C25 -55.8(2) . . . . ?
C18 N4 C24 C25 62.1(2) . . . . ?
N4 C24 C25 C26 -166.78(18) . . . . ?

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 H1 O1 0.88 2.12 2.695(2) 122.6 .
N1 H1 O3 0.88 2.31 3.048(2) 141.9 4_566
N3 H2 O1 0.88 2.13 2.676(2) 119.4 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        66.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_40422m
_database_code_depnum_ccdc_archive 'CCDC 1420542'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H30 N3 Na O8'
_chemical_formula_sum            'C24 H30 N3 Na O8'
_chemical_formula_weight         511.50

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'
Na Na 0.1353 0.1239 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   7.916(3)
_cell_length_b                   16.599(6)
_cell_length_c                   18.426(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.920(6)
_cell_angle_gamma                90.00
_cell_volume                     2412.2(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    2276
_cell_measurement_theta_min      25.9
_cell_measurement_theta_max      68.2

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1080
_exptl_absorpt_coefficient_mu    1.039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7321
_exptl_absorpt_correction_T_max  0.9795
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15581
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         6.84
_diffrn_reflns_theta_max         66.00
_reflns_number_total             4116
_reflns_number_gt                3795
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0660P)²+0.8397P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4116
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.33920(16) 0.13410(8) 0.11259(7) 0.0249(3) Uani 1 1 d . . .
H1 H 0.3512 0.1724 0.1457 0.030 Uiso 1 1 calc R . .
N2 N 0.51076(16) 0.16625(8) 0.39467(7) 0.0237(3) Uani 1 1 d . . .
H2 H 0.4709 0.1947 0.3567 0.028 Uiso 1 1 calc R . .
N3 N 0.32118(16) 0.33952(8) 0.23761(7) 0.0254(3) Uani 1 1 d . . .
C1 C 0.2689(2) 0.14415(11) 0.04318(9) 0.0331(4) Uani 1 1 d . . .
H3 H 0.2240 0.1929 0.0226 0.040 Uiso 1 1 calc R . .
C2 C 0.2741(3) 0.07159(12) 0.00828(9) 0.0402(5) Uani 1 1 d . . .
H4 H 0.2346 0.0610 -0.0409 0.048 Uiso 1 1 calc R . .
C3 C 0.3485(2) 0.01544(11) 0.05848(9) 0.0345(4) Uani 1 1 d . . .
H5 H 0.3677 -0.0400 0.0494 0.041 Uiso 1 1 calc R . .
C4 C 0.38870(19) 0.05538(10) 0.12338(8) 0.0238(3) Uani 1 1 d . . .
C5 C 0.53754(18) -0.05067(9) 0.19571(8) 0.0218(3) Uani 1 1 d . . .
H6 H 0.5405 -0.0813 0.1523 0.026 Uiso 1 1 calc R . .
C6 C 0.46663(18) 0.02513(9) 0.19291(8) 0.0208(3) Uani 1 1 d . . .
C7 C 0.46809(18) 0.07327(9) 0.25821(8) 0.0194(3) Uani 1 1 d . . .
C8 C 0.54462(18) 0.03916(9) 0.32540(8) 0.0203(3) Uani 1 1 d . . .
C9 C 0.60683(18) -0.03852(9) 0.32620(8) 0.0215(3) Uani 1 1 d . . .
H7 H 0.6512 -0.0621 0.3708 0.026 Uiso 1 1 calc R . .
C10 C 0.39531(19) 0.41752(9) 0.23839(8) 0.0219(3) Uani 1 1 d . . .
C11 C 0.55781(19) 0.08656(9) 0.39254(8) 0.0215(3) Uani 1 1 d . . .
C12 C 0.6152(2) 0.06512(10) 0.46271(8) 0.0258(3) Uani 1 1 d . . .
H8 H 0.6582 0.0139 0.4781 0.031 Uiso 1 1 calc R . .
C13 C 0.5985(2) 0.13297(10) 0.50744(9) 0.0292(4) Uani 1 1 d . . .
H9 H 0.6263 0.1354 0.5586 0.035 Uiso 1 1 calc R . .
C14 C 0.5348(2) 0.19480(10) 0.46407(9) 0.0279(4) Uani 1 1 d . . .
H10 H 0.5117 0.2480 0.4796 0.033 Uiso 1 1 calc R . .
C15 C -0.2298(2) 0.27577(10) 0.20669(8) 0.0276(4) Uani 1 1 d . . .
H11 H -0.2941 0.3264 0.1974 0.033 Uiso 1 1 calc R . .
H12 H -0.3102 0.2327 0.2176 0.033 Uiso 1 1 calc R . .
C16 C -0.1376(2) 0.25339(10) 0.14126(8) 0.0281(4) Uani 1 1 d . . .
H13 H -0.2208 0.2464 0.0985 0.034 Uiso 1 1 calc R . .
H14 H -0.0599 0.2977 0.1304 0.034 Uiso 1 1 calc R . .
C17 C -0.1418(2) 0.11065(10) 0.13745(9) 0.0299(4) Uani 1 1 d . . .
H15 H -0.1617 0.1032 0.0841 0.036 Uiso 1 1 calc R . .
H16 H -0.2531 0.1157 0.1578 0.036 Uiso 1 1 calc R . .
C18 C -0.0467(2) 0.04045(10) 0.17086(9) 0.0294(4) Uani 1 1 d . . .
H17 H -0.1116 -0.0099 0.1608 0.035 Uiso 1 1 calc R . .
H18 H 0.0645 0.0351 0.1505 0.035 Uiso 1 1 calc R . .
C19 C 0.0503(2) -0.01148(9) 0.28706(9) 0.0291(4) Uani 1 1 d . . .
H19 H 0.1690 -0.0194 0.2755 0.035 Uiso 1 1 calc R . .
H20 H -0.0141 -0.0614 0.2745 0.035 Uiso 1 1 calc R . .
C20 C 0.0448(2) 0.00733(10) 0.36579(9) 0.0294(4) Uani 1 1 d . . .
H21 H -0.0737 0.0173 0.3768 0.035 Uiso 1 1 calc R . .
H22 H 0.0896 -0.0387 0.3957 0.035 Uiso 1 1 calc R . .
C21 C 0.1179(2) 0.11179(10) 0.45080(8) 0.0284(4) Uani 1 1 d . . .
H23 H 0.2271 0.1316 0.4744 0.034 Uiso 1 1 calc R . .
H24 H 0.0739 0.0702 0.4827 0.034 Uiso 1 1 calc R . .
C22 C -0.0058(2) 0.18023(10) 0.44206(8) 0.0267(4) Uani 1 1 d . . .
H25 H -0.1150 0.1615 0.4176 0.032 Uiso 1 1 calc R . .
H26 H -0.0269 0.2027 0.4902 0.032 Uiso 1 1 calc R . .
C23 C -0.0279(2) 0.31203(10) 0.39017(9) 0.0288(4) Uani 1 1 d . . .
H27 H 0.0478 0.3563 0.3773 0.035 Uiso 1 1 calc R . .
H28 H -0.0727 0.3260 0.4371 0.035 Uiso 1 1 calc R . .
C24 C -0.1731(2) 0.30549(10) 0.33238(8) 0.0286(4) Uani 1 1 d . . .
H29 H -0.2530 0.2630 0.3454 0.034 Uiso 1 1 calc R . .
H30 H -0.2353 0.3572 0.3275 0.034 Uiso 1 1 calc R . .
Na1 Na 0.12627(7) 0.18372(3) 0.27651(3) 0.02157(17) Uani 1 1 d . . .
O1 O -0.04315(14) 0.18126(6) 0.15321(6) 0.0250(3) Uani 1 1 d . . .
O2 O 0.40361(13) 0.14390(6) 0.25649(6) 0.0230(2) Uani 1 1 d . . .
O3 O -0.10378(13) 0.28580(6) 0.26596(5) 0.0240(3) Uani 1 1 d . . .
O4 O 0.30627(15) 0.30495(7) 0.29682(6) 0.0302(3) Uani 1 1 d . . .
O5 O 0.06810(13) 0.23968(6) 0.39894(5) 0.0241(3) Uani 1 1 d . . .
O6 O 0.14504(14) 0.07698(7) 0.38221(6) 0.0280(3) Uani 1 1 d . . .
O7 O 0.27000(15) 0.30785(7) 0.17882(7) 0.0327(3) Uani 1 1 d . . .
O8 O -0.02348(14) 0.05471(7) 0.24712(6) 0.0274(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
N1 C1 1.361(2) . ?
N1 C4 1.374(2) . ?
N1 H1 0.8800 . ?
N2 C14 1.362(2) . ?
N2 C11 1.376(2) . ?
N2 H2 0.8800 . ?
N3 O7 1.2404(18) . ?
N3 O4 1.2472(18) . ?
N3 C10 1.421(2) . ?
C1 C2 1.368(3) . ?
C1 H3 0.9500 . ?
C2 C3 1.406(3) . ?
C2 H4 0.9500 . ?
C3 C4 1.380(2) . ?
C3 H5 0.9500 . ?
C4 C6 1.462(2) . ?
C5 C6 1.377(2) . ?
C5 C10 1.388(2) 2_645 ?
C5 H6 0.9500 . ?
C6 C7 1.444(2) . ?
C7 O2 1.2779(18) . ?
C7 C8 1.446(2) . ?
C8 C9 1.380(2) . ?
C8 C11 1.462(2) . ?
C9 C10 1.395(2) 2_645 ?
C9 H7 0.9500 . ?
C10 C5 1.388(2) 2_655 ?
C10 C9 1.395(2) 2_655 ?
C11 C12 1.380(2) . ?
C12 C13 1.409(2) . ?
C12 H8 0.9500 . ?
C13 C14 1.370(2) . ?
C13 H9 0.9500 . ?
C14 H10 0.9500 . ?
C15 O3 1.4242(19) . ?
C15 C16 1.508(2) . ?
C15 H11 0.9900 . ?
C15 H12 0.9900 . ?
C16 O1 1.4185(19) . ?
C16 H13 0.9900 . ?
C16 H14 0.9900 . ?
C17 O1 1.4246(19) . ?
C17 C18 1.492(2) . ?
C17 H15 0.9900 . ?
C17 H16 0.9900 . ?
C18 O8 1.421(2) . ?
C18 H17 0.9900 . ?
C18 H18 0.9900 . ?
C19 O8 1.420(2) . ?
C19 C20 1.488(2) . ?
C19 H19 0.9900 . ?
C19 H20 0.9900 . ?
C20 O6 1.4203(19) . ?
C20 H21 0.9900 . ?
C20 H22 0.9900 . ?
C21 O6 1.423(2) . ?
C21 C22 1.499(2) . ?
C21 H23 0.9900 . ?
C21 H24 0.9900 . ?
C22 O5 1.4239(18) . ?
C22 H25 0.9900 . ?
C22 H26 0.9900 . ?
C23 O5 1.4227(19) . ?
C23 C24 1.503(2) . ?
C23 H27 0.9900 . ?
C23 H28 0.9900 . ?
C24 O3 1.4219(19) . ?
C24 H29 0.9900 . ?
C24 H30 0.9900 . ?
Na1 O2 2.3520(14) . ?
Na1 O4 2.4754(14) . ?
Na1 O3 2.4828(13) . ?
Na1 O8 2.4848(14) . ?
Na1 O5 2.5183(13) . ?
Na1 O1 2.5375(14) . ?
Na1 O6 2.6278(14) . ?

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 N1 C4 109.96(14) . . ?
C1 N1 H1 125.0 . . ?
C4 N1 H1 125.0 . . ?
C14 N2 C11 110.18(13) . . ?
C14 N2 H2 124.9 . . ?
C11 N2 H2 124.9 . . ?
O7 N3 O4 121.37(13) . . ?
O7 N3 C10 119.91(13) . . ?
O4 N3 C10 118.71(13) . . ?
N1 C1 C2 107.91(15) . . ?
N1 C1 H3 126.0 . . ?
C2 C1 H3 126.0 . . ?
C1 C2 C3 107.59(16) . . ?
C1 C2 H4 126.2 . . ?
C3 C2 H4 126.2 . . ?
C4 C3 C2 107.69(16) . . ?
C4 C3 H5 126.2 . . ?
C2 C3 H5 126.2 . . ?
N1 C4 C3 106.84(14) . . ?
N1 C4 C6 123.16(14) . . ?
C3 C4 C6 130.00(15) . . ?
C6 C5 C10 120.33(14) . 2_645 ?
C6 C5 H6 119.8 . . ?
C10 C5 H6 119.8 2_645 . ?
C5 C6 C7 120.03(14) . . ?
C5 C6 C4 119.11(14) . . ?
C7 C6 C4 120.85(14) . . ?
O2 C7 C6 120.83(13) . . ?
O2 C7 C8 121.17(13) . . ?
C6 C7 C8 118.01(13) . . ?
C9 C8 C7 119.87(14) . . ?
C9 C8 C11 119.62(14) . . ?
C7 C8 C11 120.52(13) . . ?
C8 C9 C10 120.10(14) . 2_645 ?
C8 C9 H7 120.0 . . ?
C10 C9 H7 120.0 2_645 . ?
C5 C10 C9 121.55(14) 2_655 2_655 ?
C5 C10 N3 118.85(14) 2_655 . ?
C9 C10 N3 119.55(14) 2_655 . ?
N2 C11 C12 106.83(13) . . ?
N2 C11 C8 122.80(13) . . ?
C12 C11 C8 130.37(14) . . ?
C11 C12 C13 107.57(14) . . ?
C11 C12 H8 126.2 . . ?
C13 C12 H8 126.2 . . ?
C14 C13 C12 107.83(14) . . ?
C14 C13 H9 126.1 . . ?
C12 C13 H9 126.1 . . ?
N2 C14 C13 107.57(14) . . ?
N2 C14 H10 126.2 . . ?
C13 C14 H10 126.2 . . ?
O3 C15 C16 106.66(13) . . ?
O3 C15 H11 110.4 . . ?
C16 C15 H11 110.4 . . ?
O3 C15 H12 110.4 . . ?
C16 C15 H12 110.4 . . ?
H11 C15 H12 108.6 . . ?
O1 C16 C15 111.62(12) . . ?
O1 C16 H13 109.3 . . ?
C15 C16 H13 109.3 . . ?
O1 C16 H14 109.3 . . ?
C15 C16 H14 109.3 . . ?
H13 C16 H14 108.0 . . ?
O1 C17 C18 108.06(13) . . ?
O1 C17 H15 110.1 . . ?
C18 C17 H15 110.1 . . ?
O1 C17 H16 110.1 . . ?
C18 C17 H16 110.1 . . ?
H15 C17 H16 108.4 . . ?
O8 C18 C17 107.20(13) . . ?
O8 C18 H17 110.3 . . ?
C17 C18 H17 110.3 . . ?
O8 C18 H18 110.3 . . ?
C17 C18 H18 110.3 . . ?
H17 C18 H18 108.5 . . ?
O8 C19 C20 107.32(13) . . ?
O8 C19 H19 110.3 . . ?
C20 C19 H19 110.3 . . ?
O8 C19 H20 110.3 . . ?
C20 C19 H20 110.3 . . ?
H19 C19 H20 108.5 . . ?
O6 C20 C19 108.41(13) . . ?
O6 C20 H21 110.0 . . ?
C19 C20 H21 110.0 . . ?
O6 C20 H22 110.0 . . ?
C19 C20 H22 110.0 . . ?
H21 C20 H22 108.4 . . ?
O6 C21 C22 111.07(13) . . ?
O6 C21 H23 109.4 . . ?
C22 C21 H23 109.4 . . ?
O6 C21 H24 109.4 . . ?
C22 C21 H24 109.4 . . ?
H23 C21 H24 108.0 . . ?
O5 C22 C21 106.82(13) . . ?
O5 C22 H25 110.4 . . ?
C21 C22 H25 110.4 . . ?
O5 C22 H26 110.4 . . ?
C21 C22 H26 110.4 . . ?
H25 C22 H26 108.6 . . ?
O5 C23 C24 112.84(13) . . ?
O5 C23 H27 109.0 . . ?
C24 C23 H27 109.0 . . ?
O5 C23 H28 109.0 . . ?
C24 C23 H28 109.0 . . ?
H27 C23 H28 107.8 . . ?
O3 C24 C23 107.33(13) . . ?
O3 C24 H29 110.2 . . ?
C23 C24 H29 110.2 . . ?
O3 C24 H30 110.2 . . ?
C23 C24 H30 110.2 . . ?
H29 C24 H30 108.5 . . ?
O2 Na1 O4 73.69(5) . . ?
O2 Na1 O3 150.20(4) . . ?
O4 Na1 O3 82.30(5) . . ?
O2 Na1 O8 99.08(5) . . ?
O4 Na1 O8 172.37(5) . . ?
O3 Na1 O8 103.77(5) . . ?
O2 Na1 O5 119.28(4) . . ?
O4 Na1 O5 73.25(4) . . ?
O3 Na1 O5 68.23(4) . . ?
O8 Na1 O5 113.12(4) . . ?
O2 Na1 O1 106.49(4) . . ?
O4 Na1 O1 113.68(4) . . ?
O3 Na1 O1 67.24(4) . . ?
O8 Na1 O1 65.50(4) . . ?
O5 Na1 O1 133.21(5) . . ?
O2 Na1 O6 86.13(4) . . ?
O4 Na1 O6 116.16(5) . . ?
O3 Na1 O6 120.84(4) . . ?
O8 Na1 O6 64.92(4) . . ?
O5 Na1 O6 65.66(4) . . ?
O1 Na1 O6 130.14(4) . . ?
C16 O1 C17 112.97(13) . . ?
C16 O1 Na1 110.88(8) . . ?
C17 O1 Na1 115.74(9) . . ?
C7 O2 Na1 129.06(9) . . ?
C24 O3 C15 112.97(12) . . ?
C24 O3 Na1 115.11(9) . . ?
C15 O3 Na1 116.17(9) . . ?
N3 O4 Na1 109.77(9) . . ?
C23 O5 C22 114.05(12) . . ?
C23 O5 Na1 110.27(8) . . ?
C22 O5 Na1 111.08(9) . . ?
C20 O6 C21 113.30(12) . . ?
C20 O6 Na1 113.32(9) . . ?
C21 O6 Na1 112.42(9) . . ?
C19 O8 C18 113.33(12) . . ?
C19 O8 Na1 112.74(9) . . ?
C18 O8 Na1 112.20(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 C2 -0.6(2) . . . . ?
N1 C1 C2 C3 0.6(2) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C1 N1 C4 C3 0.30(18) . . . . ?
C1 N1 C4 C6 -179.10(14) . . . . ?
C2 C3 C4 N1 0.1(2) . . . . ?
C2 C3 C4 C6 179.43(17) . . . . ?
C10 C5 C6 C7 2.5(2) 2_645 . . . ?
C10 C5 C6 C4 -176.74(13) 2_645 . . . ?
N1 C4 C6 C5 -169.36(14) . . . . ?
C3 C4 C6 C5 11.4(3) . . . . ?
N1 C4 C6 C7 11.4(2) . . . . ?
C3 C4 C6 C7 -167.88(16) . . . . ?
C5 C6 C7 O2 179.64(13) . . . . ?
C4 C6 C7 O2 -1.1(2) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C4 C6 C7 C8 178.93(13) . . . . ?
O2 C7 C8 C9 177.28(13) . . . . ?
C6 C7 C8 C9 -2.7(2) . . . . ?
O2 C7 C8 C11 -3.2(2) . . . . ?
C6 C7 C8 C11 176.81(13) . . . . ?
C7 C8 C9 C10 3.6(2) . . . 2_645 ?
C11 C8 C9 C10 -175.94(13) . . . 2_645 ?
O7 N3 C10 C5 -175.50(13) . . . 2_655 ?
O4 N3 C10 C5 5.8(2) . . . 2_655 ?
O7 N3 C10 C9 7.0(2) . . . 2_655 ?
O4 N3 C10 C9 -171.69(13) . . . 2_655 ?
C14 N2 C11 C12 -0.83(17) . . . . ?
C14 N2 C11 C8 179.34(13) . . . . ?
C9 C8 C11 N2 174.79(13) . . . . ?
C7 C8 C11 N2 -4.8(2) . . . . ?
C9 C8 C11 C12 -5.0(2) . . . . ?
C7 C8 C11 C12 175.45(15) . . . . ?
N2 C11 C12 C13 1.23(17) . . . . ?
C8 C11 C12 C13 -178.96(15) . . . . ?
C11 C12 C13 C14 -1.19(18) . . . . ?
C11 N2 C14 C13 0.09(18) . . . . ?
C12 C13 C14 N2 0.68(18) . . . . ?
O3 C15 C16 O1 59.57(17) . . . . ?
O1 C17 C18 O8 60.12(16) . . . . ?
O8 C19 C20 O6 -62.67(16) . . . . ?
O6 C21 C22 O5 -62.03(16) . . . . ?
O5 C23 C24 O3 -58.94(17) . . . . ?
C15 C16 O1 C17 85.13(16) . . . . ?
C15 C16 O1 Na1 -46.67(15) . . . . ?
C18 C17 O1 C16 -164.42(12) . . . . ?
C18 C17 O1 Na1 -35.07(15) . . . . ?
O2 Na1 O1 C16 -131.89(9) . . . . ?
O4 Na1 O1 C16 -52.84(10) . . . . ?
O3 Na1 O1 C16 17.12(9) . . . . ?
O8 Na1 O1 C16 135.47(10) . . . . ?
O5 Na1 O1 C16 36.03(11) . . . . ?
O6 Na1 O1 C16 129.04(9) . . . . ?
O2 Na1 O1 C17 97.75(10) . . . . ?
O4 Na1 O1 C17 176.80(10) . . . . ?
O3 Na1 O1 C17 -113.24(11) . . . . ?
O8 Na1 O1 C17 5.11(10) . . . . ?
O5 Na1 O1 C17 -94.33(11) . . . . ?
O6 Na1 O1 C17 -1.32(12) . . . . ?
C6 C7 O2 Na1 91.94(15) . . . . ?
C8 C7 O2 Na1 -88.08(16) . . . . ?
O4 Na1 O2 C7 158.91(13) . . . . ?
O3 Na1 O2 C7 -163.45(11) . . . . ?
O8 Na1 O2 C7 -23.60(13) . . . . ?
O5 Na1 O2 C7 99.46(12) . . . . ?
O1 Na1 O2 C7 -90.61(12) . . . . ?
O6 Na1 O2 C7 40.22(12) . . . . ?
C23 C24 O3 C15 178.49(13) . . . . ?
C23 C24 O3 Na1 41.81(15) . . . . ?
C16 C15 O3 C24 -178.71(13) . . . . ?
C16 C15 O3 Na1 -42.51(15) . . . . ?
O2 Na1 O3 C24 -126.24(12) . . . . ?
O4 Na1 O3 C24 -89.98(11) . . . . ?
O8 Na1 O3 C24 94.73(11) . . . . ?
O5 Na1 O3 C24 -14.99(10) . . . . ?
O1 Na1 O3 C24 150.27(11) . . . . ?
O6 Na1 O3 C24 25.96(12) . . . . ?
O2 Na1 O3 C15 98.50(13) . . . . ?
O4 Na1 O3 C15 134.76(10) . . . . ?
O8 Na1 O3 C15 -40.54(10) . . . . ?
O5 Na1 O3 C15 -150.26(10) . . . . ?
O1 Na1 O3 C15 15.01(9) . . . . ?
O6 Na1 O3 C15 -109.31(10) . . . . ?
O7 N3 O4 Na1 -9.17(16) . . . . ?
C10 N3 O4 Na1 169.47(10) . . . . ?
O2 Na1 O4 N3 85.39(9) . . . . ?
O3 Na1 O4 N3 -76.78(9) . . . . ?
O8 Na1 O4 N3 66.3(4) . . . . ?
O5 Na1 O4 N3 -146.29(10) . . . . ?
O1 Na1 O4 N3 -15.83(10) . . . . ?
O6 Na1 O4 N3 162.56(9) . . . . ?
C24 C23 O5 C22 -80.50(16) . . . . ?
C24 C23 O5 Na1 45.29(15) . . . . ?
C21 C22 O5 C23 -175.29(12) . . . . ?
C21 C22 O5 Na1 59.36(13) . . . . ?
O2 Na1 O5 C23 131.90(9) . . . . ?
O4 Na1 O5 C23 72.22(10) . . . . ?
O3 Na1 O5 C23 -16.03(9) . . . . ?
O8 Na1 O5 C23 -112.24(10) . . . . ?
O1 Na1 O5 C23 -34.81(11) . . . . ?
O6 Na1 O5 C23 -157.89(10) . . . . ?
O2 Na1 O5 C22 -100.66(10) . . . . ?
O4 Na1 O5 C22 -160.34(10) . . . . ?
O3 Na1 O5 C22 111.41(10) . . . . ?
O8 Na1 O5 C22 15.20(11) . . . . ?
O1 Na1 O5 C22 92.64(11) . . . . ?
O6 Na1 O5 C22 -30.45(9) . . . . ?
C19 C20 O6 C21 166.00(13) . . . . ?
C19 C20 O6 Na1 36.38(15) . . . . ?
C22 C21 O6 C20 -96.95(16) . . . . ?
C22 C21 O6 Na1 33.13(15) . . . . ?
O2 Na1 O6 C20 -107.58(10) . . . . ?
O4 Na1 O6 C20 -177.29(9) . . . . ?
O3 Na1 O6 C20 85.85(11) . . . . ?
O8 Na1 O6 C20 -5.67(9) . . . . ?
O5 Na1 O6 C20 127.77(10) . . . . ?
O1 Na1 O6 C20 0.79(12) . . . . ?
O2 Na1 O6 C21 122.35(10) . . . . ?
O4 Na1 O6 C21 52.63(11) . . . . ?
O3 Na1 O6 C21 -44.22(11) . . . . ?
O8 Na1 O6 C21 -135.74(10) . . . . ?
O5 Na1 O6 C21 -2.30(9) . . . . ?
O1 Na1 O6 C21 -129.29(10) . . . . ?
C20 C19 O8 C18 -172.28(13) . . . . ?
C20 C19 O8 Na1 58.88(13) . . . . ?
C17 C18 O8 C19 173.81(13) . . . . ?
C17 C18 O8 Na1 -57.09(14) . . . . ?
O2 Na1 O8 C19 53.23(10) . . . . ?
O4 Na1 O8 C19 71.7(4) . . . . ?
O3 Na1 O8 C19 -146.04(9) . . . . ?
O5 Na1 O8 C19 -74.12(10) . . . . ?
O1 Na1 O8 C19 157.29(10) . . . . ?
O6 Na1 O8 C19 -28.13(9) . . . . ?
O2 Na1 O8 C18 -76.19(10) . . . . ?
O4 Na1 O8 C18 -57.7(4) . . . . ?
O3 Na1 O8 C18 84.55(10) . . . . ?
O5 Na1 O8 C18 156.46(9) . . . . ?
O1 Na1 O8 C18 27.88(10) . . . . ?
O6 Na1 O8 C18 -157.54(11) . . . . ?

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 H1 O2 0.88 2.10 2.6617(18) 120.7 .
N1 H1 O7 0.88 2.43 3.197(2) 145.7 .
N2 H2 O2 0.88 2.06 2.6399(18) 122.8 .
N2 H2 O4 0.88 2.45 3.2666(19) 153.9 .

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        66.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1420543'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Py2PhO-_KOH+18-crown-6-ether
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H44 K N6 O12, C12 H24 K O8'
_chemical_formula_sum            'C26 H36 K N3 O10'
_chemical_formula_weight         589.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C -0.0020 0.0020 '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 -0.0031 0.0041 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0041 0.0075 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.1827 0.3026 '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                   10.778(3)
_cell_length_b                   10.915(3)
_cell_length_c                   14.506(4)
_cell_angle_alpha                82.963(5)
_cell_angle_beta                 86.231(4)
_cell_angle_gamma                63.226(4)
_cell_volume                     1512.0(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11210
_cell_measurement_theta_min      1.558
_cell_measurement_theta_max      27.499

_exptl_crystal_description       Needle
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.297
_shelx_estimated_absorpt_T_min   0.994
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.000
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (T.Higashi, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.78291
_diffrn_radiation_type           Synchrotron
_diffrn_source                   'synchrotron radiation SPring-8 BL40XU'
_diffrn_radiation_monochromator  'Si(111) Channel Cut'
_diffrn_measurement_device_type  'Rigaku Saturn 724'
_diffrn_measurement_method       'Oscillation Photograph'
_diffrn_detector_area_resol_mean 29
_diffrn_reflns_number            11255
_diffrn_reflns_av_unetI/netI     0.5559
_diffrn_reflns_av_R_equivalents  0.1151
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.558
_diffrn_reflns_theta_max         27.665
_diffrn_reflns_theta_full        27.665
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             5121
_reflns_number_gt                2823
_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       'Rapid Auto(Rigaku)'
_computing_cell_refinement       'Rapid Auto(Rigaku)'
_computing_data_reduction        'Rapid Auto(Rigaku)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0622P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5121
_refine_ls_number_parameters     370
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1756
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1435
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.973
_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 0.2250(3) -0.0567(3) 0.30432(17) 0.0214(7) Uani 1 1 d . . . . .
H1 H 0.2875 -0.1369 0.3293 0.026 Uiso 1 1 calc R U . . .
N2 N 0.7971(3) -0.3449(3) 0.27984(18) 0.0260(8) Uani 1 1 d . . . . .
H2A H 0.7279 -0.3592 0.3056 0.031 Uiso 1 1 calc R U . . .
N3 N 0.5430(3) 0.2979(3) 0.19793(17) 0.0223(7) Uani 1 1 d . . . . .
O1 O 0.5161(2) -0.2014(2) 0.30078(14) 0.0232(6) Uani 1 1 d D . . . .
O2 O 0.4317(3) 0.4075(2) 0.18192(15) 0.0295(7) Uani 1 1 d . . . . .
O3 O 0.6604(2) 0.2999(2) 0.19497(15) 0.0306(7) Uani 1 1 d . . . . .
O4 O 0.2071(2) 0.6085(2) 0.00542(14) 0.0255(6) Uani 1 1 d . . . . .
O5 O 0.3318(2) 0.7911(2) 0.01814(14) 0.0257(6) Uani 1 1 d . . . . .
O6 O 0.6230(2) 0.6602(2) 0.05588(14) 0.0258(6) Uani 1 1 d . . . . .
O7 O 0.7397(2) -0.7608(2) 0.49828(14) 0.0294(7) Uani 1 1 d . . . . .
O8 O 0.4784(2) -0.7332(2) 0.44287(14) 0.0246(6) Uani 1 1 d . . . . .
O9 O 0.2299(2) -0.4923(2) 0.49050(15) 0.0302(7) Uani 1 1 d . . . . .
O10A O 0.4328(4) -0.4086(3) 0.31323(19) 0.0288(11) Uiso 0.819(9) 1 d D . P A 1
H10A H 0.475(4) -0.343(3) 0.289(2) 0.043 Uiso 0.819(9) 1 d D U P A 1
H10B H 0.429(4) -0.450(3) 0.2554(17) 0.043 Uiso 0.819(9) 1 d D U P A 1
O10B O 0.534(2) -0.4571(16) 0.3173(11) 0.059(6) Uiso 0.181(9) 1 d D . P A 2
H10C H 0.5353 -0.3642 0.3142 0.089 Uiso 0.181(9) 1 d DR U P A 2
H10D H 0.5352 -0.4911 0.2434 0.089 Uiso 0.181(9) 1 d DR U P A 2
K1 K 0.5000 0.5000 0.0000 0.0220(3) Uani 1 2 d S . P . .
K2 K 0.5000 -0.5000 0.5000 0.0294(3) Uani 1 2 d S . P . .
C1 C 0.0835(4) -0.0190(3) 0.2990(2) 0.0265(9) Uani 1 1 d . . . . .
H1A H 0.0390 -0.0748 0.3217 0.032 Uiso 1 1 calc R U . . .
C2 C 0.0191(4) 0.1132(3) 0.2551(2) 0.0238(9) Uani 1 1 d . . . . .
H2 H -0.0772 0.1652 0.2422 0.029 Uiso 1 1 calc R U . . .
C3 C 0.1260(4) 0.1575(4) 0.2325(2) 0.0266(9) Uani 1 1 d . . . . .
H3 H 0.1126 0.2443 0.2014 0.032 Uiso 1 1 calc R U . . .
C4 C 0.2533(4) 0.0504(3) 0.2645(2) 0.0200(8) Uani 1 1 d . . . . .
C5 C 0.3941(3) 0.0448(3) 0.2561(2) 0.0175(8) Uani 1 1 d . . . . .
C6 C 0.4051(4) 0.1689(3) 0.23303(19) 0.0199(8) Uani 1 1 d . . . . .
H6 H 0.3235 0.2543 0.2269 0.024 Uiso 1 1 calc R U . . .
C7 C 0.5376(4) 0.1667(3) 0.2189(2) 0.0188(8) Uani 1 1 d . . . . .
C8 C 0.6609(4) 0.0432(3) 0.2250(2) 0.0230(9) Uani 1 1 d . . . . .
H8 H 0.7476 0.0455 0.2134 0.028 Uiso 1 1 calc R U . . .
C9 C 0.6571(3) -0.0847(3) 0.2481(2) 0.0180(8) Uani 1 1 d . . . . .
C10 C 0.5207(4) -0.0857(3) 0.2701(2) 0.0206(9) Uani 1 1 d . . . . .
C11 C 0.7886(4) -0.2152(3) 0.2468(2) 0.0208(9) Uani 1 1 d . . . . .
C12 C 0.9212(4) -0.2394(4) 0.2115(2) 0.0262(9) Uani 1 1 d . . . . .
H12 H 0.9476 -0.1709 0.1841 0.031 Uiso 1 1 calc R U . . .
C13 C 1.0101(4) -0.3851(4) 0.2238(2) 0.0310(10) Uani 1 1 d . . . . .
H13 H 1.1055 -0.4308 0.2065 0.037 Uiso 1 1 calc R U . . .
C14 C 0.9289(4) -0.4463(4) 0.2661(2) 0.0278(9) Uani 1 1 d . . . . .
H14 H 0.9598 -0.5424 0.2828 0.033 Uiso 1 1 calc R U . . .
C15 C 0.1572(4) 0.5451(3) -0.0563(2) 0.0301(10) Uani 1 1 d . . . . .
H15 H 0.1763 0.5701 -0.1217 0.036 Uiso 1 1 calc R U . . .
H15A H 0.0556 0.5786 -0.0480 0.036 Uiso 1 1 calc R U . . .
C16 C 0.1288(4) 0.7587(3) -0.0064(2) 0.0274(9) Uani 1 1 d . . . . .
H16 H 0.0304 0.7869 0.0119 0.033 Uiso 1 1 calc R U . . .
H16A H 0.1323 0.7940 -0.0722 0.033 Uiso 1 1 calc R U . . .
C17 C 0.1945(4) 0.8175(4) 0.0552(2) 0.0297(9) Uani 1 1 d . . . . .
H17 H 0.1360 0.9180 0.0560 0.036 Uiso 1 1 calc R U . . .
H17A H 0.2020 0.7730 0.1197 0.036 Uiso 1 1 calc R U . . .
C18 C 0.3970(4) 0.8509(4) 0.0714(2) 0.0289(10) Uani 1 1 d . . . . .
H18 H 0.3971 0.8181 0.1381 0.035 Uiso 1 1 calc R U . . .
H18A H 0.3441 0.9527 0.0641 0.035 Uiso 1 1 calc R U . . .
C19 C 0.5449(4) 0.8083(3) 0.0365(2) 0.0262(9) Uani 1 1 d . . . . .
H19 H 0.5453 0.8353 -0.0311 0.031 Uiso 1 1 calc R U . . .
H19A H 0.5877 0.8550 0.0681 0.031 Uiso 1 1 calc R U . . .
C20 C 0.7686(4) 0.6111(4) 0.0332(2) 0.0311(10) Uani 1 1 d . . . . .
H20 H 0.8093 0.6553 0.0691 0.037 Uiso 1 1 calc R U . . .
H20A H 0.7803 0.6353 -0.0338 0.037 Uiso 1 1 calc R U . . .
C21 C 0.8678(4) -0.7470(4) 0.4790(2) 0.0301(9) Uani 1 1 d . . . . .
H21 H 0.8714 -0.7130 0.4129 0.036 Uiso 1 1 calc R U . . .
H21A H 0.9492 -0.8379 0.4915 0.036 Uiso 1 1 calc R U . . .
C22 C 0.7290(4) -0.8561(3) 0.4407(2) 0.0283(9) Uani 1 1 d . . . . .
H22 H 0.8094 -0.9482 0.4515 0.034 Uiso 1 1 calc R U . . .
H22A H 0.7289 -0.8221 0.3742 0.034 Uiso 1 1 calc R U . . .
C23 C 0.5942(4) -0.8662(4) 0.4662(2) 0.0307(10) Uani 1 1 d . . . . .
H23 H 0.5882 -0.9362 0.4318 0.037 Uiso 1 1 calc R U . . .
H23A H 0.5920 -0.8947 0.5336 0.037 Uiso 1 1 calc R U . . .
C24 C 0.3464(4) -0.7343(3) 0.4653(2) 0.0260(9) Uani 1 1 d . . . . .
H24 H 0.3383 -0.7556 0.5331 0.031 Uiso 1 1 calc R U . . .
H24A H 0.3385 -0.8056 0.4334 0.031 Uiso 1 1 calc R U . . .
C25 C 0.2320(4) -0.5920(3) 0.4332(2) 0.0296(10) Uani 1 1 d . . . . .
H25 H 0.2488 -0.5655 0.3676 0.035 Uiso 1 1 calc R U . . .
H25A H 0.1410 -0.5941 0.4374 0.035 Uiso 1 1 calc R U . . .
C26 C 0.1287(4) -0.3542(3) 0.4592(2) 0.0333(10) Uani 1 1 d . . . . .
H26 H 0.0347 -0.3497 0.4614 0.040 Uiso 1 1 calc R U . . .
H26A H 0.1497 -0.3293 0.3941 0.040 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 C4 1.387(3) . ?
N1 C1 1.395(4) . ?
N2 C14 1.372(4) . ?
N2 C11 1.402(3) . ?
N3 O2 1.264(3) . ?
N3 O3 1.274(3) . ?
N3 C7 1.453(3) . ?
N3 K1 3.321(2) . ?
O1 C10 1.308(3) . ?
O2 K1 2.879(2) . ?
O3 K1 3.389(2) . ?
O4 C15 1.455(3) . ?
O4 C16 1.461(4) . ?
O4 K1 2.828(2) . ?
O5 C17 1.453(4) . ?
O5 C18 1.458(3) . ?
O5 K1 2.899(2) . ?
O6 C20 1.441(4) . ?
O6 C19 1.447(4) . ?
O6 K1 2.8373(18) . ?
O7 C22 1.458(4) . ?
O7 C21 1.460(4) . ?
O7 K2 2.857(2) . ?
O8 C23 1.443(4) . ?
O8 C24 1.443(4) . ?
O8 K2 2.880(2) . ?
O9 C25 1.439(4) . ?
O9 C26 1.444(4) . ?
O9 K2 2.886(2) . ?
O10A K2 2.794(3) . ?
O10B K2 2.664(16) . ?
K1 O4 2.828(2) 2_665 ?
K1 O6 2.8373(18) 2_665 ?
K1 O2 2.879(2) 2_665 ?
K1 O5 2.899(2) 2_665 ?
K1 N3 3.321(2) 2_665 ?
K1 O3 3.389(2) 2_665 ?
K2 O10B 2.664(16) 2_646 ?
K2 O10A 2.794(3) 2_646 ?
K2 O7 2.857(2) 2_646 ?
K2 O8 2.880(2) 2_646 ?
K2 O9 2.886(2) 2_646 ?
C1 C2 1.378(4) . ?
C2 C3 1.443(4) . ?
C3 C4 1.403(5) . ?
C4 C5 1.488(4) . ?
C5 C6 1.411(4) . ?
C5 C10 1.465(5) . ?
C6 C7 1.418(4) . ?
C7 C8 1.401(5) . ?
C8 C9 1.414(4) . ?
C9 C10 1.487(4) . ?
C9 C11 1.490(5) . ?
C11 C12 1.404(5) . ?
C12 C13 1.435(5) . ?
C13 C14 1.395(4) . ?
C15 C20 1.524(5) 2_665 ?
C16 C17 1.530(4) . ?
C18 C19 1.515(5) . ?
C20 C15 1.524(5) 2_665 ?
C21 C26 1.520(4) 2_646 ?
C22 C23 1.525(5) . ?
C24 C25 1.524(5) . ?
C26 C21 1.520(4) 2_646 ?

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
C4 N1 C1 110.2(3) . . ?
C14 N2 C11 110.2(3) . . ?
O2 N3 O3 121.2(2) . . ?
O2 N3 C7 119.7(2) . . ?
O3 N3 C7 119.2(3) . . ?
O2 N3 K1 58.89(14) . . ?
O3 N3 K1 82.08(14) . . ?
C7 N3 K1 131.19(17) . . ?
N3 O2 K1 99.03(18) . . ?
N3 O3 K1 76.06(16) . . ?
C15 O4 C16 111.3(2) . . ?
C15 O4 K1 112.14(19) . . ?
C16 O4 K1 116.30(15) . . ?
C17 O5 C18 111.1(3) . . ?
C17 O5 K1 111.06(17) . . ?
C18 O5 K1 114.0(2) . . ?
C20 O6 C19 112.8(2) . . ?
C20 O6 K1 114.88(18) . . ?
C19 O6 K1 116.25(16) . . ?
C22 O7 C21 111.8(2) . . ?
C22 O7 K2 115.21(18) . . ?
C21 O7 K2 112.51(18) . . ?
C23 O8 C24 112.2(2) . . ?
C23 O8 K2 115.88(16) . . ?
C24 O8 K2 114.09(19) . . ?
C25 O9 C26 111.8(2) . . ?
C25 O9 K2 111.96(19) . . ?
C26 O9 K2 109.82(15) . . ?
O4 K1 O4 180.0 2_665 . ?
O4 K1 O6 61.27(6) 2_665 . ?
O4 K1 O6 118.73(6) . . ?
O4 K1 O6 118.73(6) 2_665 2_665 ?
O4 K1 O6 61.27(6) . 2_665 ?
O6 K1 O6 180.00(6) . 2_665 ?
O4 K1 O2 74.32(6) 2_665 2_665 ?
O4 K1 O2 105.68(6) . 2_665 ?
O6 K1 O2 82.05(6) . 2_665 ?
O6 K1 O2 97.95(6) 2_665 2_665 ?
O4 K1 O2 105.68(6) 2_665 . ?
O4 K1 O2 74.32(6) . . ?
O6 K1 O2 97.95(6) . . ?
O6 K1 O2 82.05(6) 2_665 . ?
O2 K1 O2 180.00(10) 2_665 . ?
O4 K1 O5 119.40(5) 2_665 . ?
O4 K1 O5 60.60(5) . . ?
O6 K1 O5 59.82(6) . . ?
O6 K1 O5 120.18(6) 2_665 . ?
O2 K1 O5 84.90(7) 2_665 . ?
O2 K1 O5 95.10(7) . . ?
O4 K1 O5 60.60(5) 2_665 2_665 ?
O4 K1 O5 119.40(5) . 2_665 ?
O6 K1 O5 120.18(6) . 2_665 ?
O6 K1 O5 59.82(6) 2_665 2_665 ?
O2 K1 O5 95.10(7) 2_665 2_665 ?
O2 K1 O5 84.90(7) . 2_665 ?
O5 K1 O5 180.0 . 2_665 ?
O4 K1 N3 85.96(6) 2_665 . ?
O4 K1 N3 94.04(6) . . ?
O6 K1 N3 97.31(6) . . ?
O6 K1 N3 82.69(6) 2_665 . ?
O2 K1 N3 157.91(7) 2_665 . ?
O2 K1 N3 22.09(7) . . ?
O5 K1 N3 114.01(7) . . ?
O5 K1 N3 65.99(7) 2_665 . ?
O4 K1 N3 94.04(6) 2_665 2_665 ?
O4 K1 N3 85.96(6) . 2_665 ?
O6 K1 N3 82.69(6) . 2_665 ?
O6 K1 N3 97.31(6) 2_665 2_665 ?
O2 K1 N3 22.09(7) 2_665 2_665 ?
O2 K1 N3 157.91(7) . 2_665 ?
O5 K1 N3 65.99(7) . 2_665 ?
O5 K1 N3 114.01(7) 2_665 2_665 ?
N3 K1 N3 180.0 . 2_665 ?
O4 K1 O3 114.55(5) 2_665 2_665 ?
O4 K1 O3 65.45(5) . 2_665 ?
O6 K1 O3 99.28(5) . 2_665 ?
O6 K1 O3 80.72(5) 2_665 2_665 ?
O2 K1 O3 40.29(6) 2_665 2_665 ?
O2 K1 O3 139.71(6) . 2_665 ?
O5 K1 O3 63.74(6) . 2_665 ?
O5 K1 O3 116.26(6) 2_665 2_665 ?
N3 K1 O3 158.14(6) . 2_665 ?
N3 K1 O3 21.86(6) 2_665 2_665 ?
O4 K1 O3 65.45(5) 2_665 . ?
O4 K1 O3 114.55(5) . . ?
O6 K1 O3 80.72(5) . . ?
O6 K1 O3 99.28(5) 2_665 . ?
O2 K1 O3 139.71(6) 2_665 . ?
O2 K1 O3 40.29(6) . . ?
O5 K1 O3 116.26(6) . . ?
O5 K1 O3 63.74(6) 2_665 . ?
N3 K1 O3 21.86(6) . . ?
N3 K1 O3 158.14(6) 2_665 . ?
O3 K1 O3 180.0 2_665 . ?
O10B K2 O10B 180.0 . 2_646 ?
O10A K2 O10A 180.0 . 2_646 ?
O10B K2 O7 88.3(4) . . ?
O10B K2 O7 91.7(4) 2_646 . ?
O10A K2 O7 105.04(9) . . ?
O10A K2 O7 74.96(9) 2_646 . ?
O10B K2 O7 91.7(4) . 2_646 ?
O10B K2 O7 88.3(4) 2_646 2_646 ?
O10A K2 O7 74.96(9) . 2_646 ?
O10A K2 O7 105.04(9) 2_646 2_646 ?
O7 K2 O7 180.0 . 2_646 ?
O10B K2 O8 80.6(3) . . ?
O10B K2 O8 99.4(3) 2_646 . ?
O10A K2 O8 79.81(7) . . ?
O10A K2 O8 100.19(7) 2_646 . ?
O7 K2 O8 59.64(6) . . ?
O7 K2 O8 120.36(6) 2_646 . ?
O10B K2 O8 99.4(3) . 2_646 ?
O10B K2 O8 80.6(3) 2_646 2_646 ?
O10A K2 O8 100.19(7) . 2_646 ?
O10A K2 O8 79.81(7) 2_646 2_646 ?
O7 K2 O8 120.36(6) . 2_646 ?
O7 K2 O8 59.64(6) 2_646 2_646 ?
O8 K2 O8 180.0 . 2_646 ?
O10B K2 O9 95.8(4) . . ?
O10B K2 O9 84.2(4) 2_646 . ?
O10A K2 O9 77.75(8) . . ?
O10A K2 O9 102.25(8) 2_646 . ?
O7 K2 O9 118.20(6) . . ?
O7 K2 O9 61.80(6) 2_646 . ?
O8 K2 O9 60.44(7) . . ?
O8 K2 O9 119.56(7) 2_646 . ?
O10B K2 O9 84.2(4) . 2_646 ?
O10B K2 O9 95.8(4) 2_646 2_646 ?
O10A K2 O9 102.25(8) . 2_646 ?
O10A K2 O9 77.75(8) 2_646 2_646 ?
O7 K2 O9 61.80(6) . 2_646 ?
O7 K2 O9 118.20(6) 2_646 2_646 ?
O8 K2 O9 119.56(7) . 2_646 ?
O8 K2 O9 60.44(7) 2_646 2_646 ?
O9 K2 O9 180.0 . 2_646 ?
C2 C1 N1 108.3(2) . . ?
C1 C2 C3 106.8(3) . . ?
C4 C3 C2 108.3(3) . . ?
N1 C4 C3 106.4(2) . . ?
N1 C4 C5 124.8(3) . . ?
C3 C4 C5 128.8(2) . . ?
C6 C5 C10 119.4(3) . . ?
C6 C5 C4 118.7(3) . . ?
C10 C5 C4 121.9(2) . . ?
C5 C6 C7 120.3(3) . . ?
C8 C7 C6 122.0(3) . . ?
C8 C7 N3 120.0(3) . . ?
C6 C7 N3 118.0(3) . . ?
C7 C8 C9 120.5(3) . . ?
C8 C9 C10 118.9(3) . . ?
C8 C9 C11 119.4(3) . . ?
C10 C9 C11 121.6(2) . . ?
O1 C10 C5 121.7(3) . . ?
O1 C10 C9 119.9(3) . . ?
C5 C10 C9 118.4(2) . . ?
N2 C11 C12 106.1(3) . . ?
N2 C11 C9 123.0(3) . . ?
C12 C11 C9 130.8(3) . . ?
C11 C12 C13 108.5(3) . . ?
C14 C13 C12 106.4(3) . . ?
N2 C14 C13 108.7(3) . . ?
O4 C15 C20 108.7(3) . 2_665 ?
O4 C16 C17 108.0(3) . . ?
O5 C17 C16 108.5(3) . . ?
O5 C18 C19 109.1(3) . . ?
O6 C19 C18 108.6(2) . . ?
O6 C20 C15 109.3(2) . 2_665 ?
O7 C21 C26 108.8(3) . 2_646 ?
O7 C22 C23 108.3(3) . . ?
O8 C23 C22 108.9(2) . . ?
O8 C24 C25 107.9(2) . . ?
O9 C25 C24 109.7(3) . . ?
O9 C26 C21 109.6(3) . 2_646 ?

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
O3 N3 O2 K1 56.4(3) . . . . ?
C7 N3 O2 K1 -122.8(2) . . . . ?
O2 N3 O3 K1 -46.1(2) . . . . ?
C7 N3 O3 K1 133.1(2) . . . . ?
C4 N1 C1 C2 0.2(4) . . . . ?
N1 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C1 N1 C4 C3 -0.6(3) . . . . ?
C1 N1 C4 C5 -178.5(3) . . . . ?
C2 C3 C4 N1 0.7(4) . . . . ?
C2 C3 C4 C5 178.5(3) . . . . ?
N1 C4 C5 C6 -166.4(3) . . . . ?
C3 C4 C5 C6 16.2(5) . . . . ?
N1 C4 C5 C10 14.3(5) . . . . ?
C3 C4 C5 C10 -163.1(3) . . . . ?
C10 C5 C6 C7 3.2(4) . . . . ?
C4 C5 C6 C7 -176.2(3) . . . . ?
C5 C6 C7 C8 1.6(5) . . . . ?
C5 C6 C7 N3 -178.3(3) . . . . ?
O2 N3 C7 C8 171.8(3) . . . . ?
O3 N3 C7 C8 -7.4(4) . . . . ?
K1 N3 C7 C8 98.8(3) . . . . ?
O2 N3 C7 C6 -8.4(4) . . . . ?
O3 N3 C7 C6 172.4(3) . . . . ?
K1 N3 C7 C6 -81.4(3) . . . . ?
C6 C7 C8 C9 -1.7(5) . . . . ?
N3 C7 C8 C9 178.1(3) . . . . ?
C7 C8 C9 C10 -2.7(4) . . . . ?
C7 C8 C9 C11 175.2(3) . . . . ?
C6 C5 C10 O1 172.9(3) . . . . ?
C4 C5 C10 O1 -7.8(4) . . . . ?
C6 C5 C10 C9 -7.4(4) . . . . ?
C4 C5 C10 C9 171.9(3) . . . . ?
C8 C9 C10 O1 -173.1(3) . . . . ?
C11 C9 C10 O1 9.1(4) . . . . ?
C8 C9 C10 C5 7.2(4) . . . . ?
C11 C9 C10 C5 -170.7(3) . . . . ?
C14 N2 C11 C12 0.0(3) . . . . ?
C14 N2 C11 C9 177.3(3) . . . . ?
C8 C9 C11 N2 171.7(3) . . . . ?
C10 C9 C11 N2 -10.4(4) . . . . ?
C8 C9 C11 C12 -11.7(5) . . . . ?
C10 C9 C11 C12 166.2(3) . . . . ?
N2 C11 C12 C13 -0.1(3) . . . . ?
C9 C11 C12 C13 -177.2(3) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C11 N2 C14 C13 0.1(3) . . . . ?
C12 C13 C14 N2 -0.2(4) . . . . ?
C16 O4 C15 C20 -173.7(3) . . . 2_665 ?
K1 O4 C15 C20 54.0(3) . . . 2_665 ?
C15 O4 C16 C17 -175.8(2) . . . . ?
K1 O4 C16 C17 -45.7(3) . . . . ?
C18 O5 C17 C16 177.2(2) . . . . ?
K1 O5 C17 C16 -54.9(3) . . . . ?
O4 C16 C17 O5 67.8(3) . . . . ?
C17 O5 C18 C19 174.2(2) . . . . ?
K1 O5 C18 C19 47.9(3) . . . . ?
C20 O6 C19 C18 -174.5(2) . . . . ?
K1 O6 C19 C18 49.8(3) . . . . ?
O5 C18 C19 O6 -64.8(3) . . . . ?
C19 O6 C20 C15 179.6(2) . . . 2_665 ?
K1 O6 C20 C15 -44.0(3) . . . 2_665 ?
C22 O7 C21 C26 179.6(3) . . . 2_646 ?
K2 O7 C21 C26 48.2(3) . . . 2_646 ?
C21 O7 C22 C23 179.1(3) . . . . ?
K2 O7 C22 C23 -50.9(3) . . . . ?
C24 O8 C23 C22 -179.9(2) . . . . ?
K2 O8 C23 C22 -46.4(3) . . . . ?
O7 C22 C23 O8 64.2(3) . . . . ?
C23 O8 C24 C25 -177.0(2) . . . . ?
K2 O8 C24 C25 48.7(3) . . . . ?
C26 O9 C25 C24 176.4(2) . . . . ?
K2 O9 C25 C24 52.7(3) . . . . ?
O8 C24 C25 O9 -69.3(3) . . . . ?
C25 O9 C26 C21 -179.2(2) . . . 2_646 ?
K2 O9 C26 C21 -54.3(3) . . . 2_646 ?

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.092



####################################################################### 
# 
# 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_50626m
_database_code_depnum_ccdc_archive 'CCDC 1420544'
_audit_update_record             
;
2015-08-25 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10 N3 O3, C7 H11 N2'
_chemical_formula_sum            'C21 H21 N5 O3'
_chemical_formula_weight         391.43

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   ' P 21/a '
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   9.516(3)
_cell_length_b                   16.738(5)
_cell_length_c                   12.250(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.800(8)
_cell_angle_gamma                90.00
_cell_volume                     1857.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1955
_cell_measurement_theta_min      25.3
_cell_measurement_theta_max      68.2

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6976
_exptl_absorpt_correction_T_max  0.9690
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12001
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         7.20
_diffrn_reflns_theta_max         66.99
_reflns_number_total             3264
_reflns_number_gt                2807
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0600P)²+0.1964P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3264
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0946
_refine_ls_wR_factor_gt          0.0929
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.21661(9) -0.03181(6) 0.30972(7) 0.0248(2) Uani 1 1 d . . .
O1 O 0.53073(9) 0.24393(5) 0.13268(7) 0.0200(2) Uani 1 1 d . . .
O2 O 0.08763(9) -0.03091(6) 0.13023(7) 0.0271(2) Uani 1 1 d . . .
C1 C 0.39780(12) 0.08642(7) 0.27976(10) 0.0180(3) Uani 1 1 d . . .
H1 H 0.4206 0.0618 0.3530 0.022 Uiso 1 1 calc R . .
N1 N 0.72024(11) 0.22451(6) 0.34059(8) 0.0196(2) Uani 1 1 d . . .
H2 H 0.7114 0.2521 0.2777 0.024 Uiso 1 1 calc R . .
N2 N 0.35273(11) 0.25778(6) -0.08094(8) 0.0188(2) Uani 1 1 d . . .
H3 H 0.4329 0.2799 -0.0348 0.023 Uiso 1 1 calc R . .
C2 C 0.23636(12) 0.09671(7) 0.08389(10) 0.0181(3) Uani 1 1 d . . .
H4 H 0.1523 0.0782 0.0251 0.022 Uiso 1 1 calc R . .
C3 C 0.32101(12) 0.15865(7) 0.06196(10) 0.0178(3) Uani 1 1 d . . .
C4 C 0.48729(12) 0.14673(7) 0.26078(10) 0.0176(3) Uani 1 1 d . . .
C5 C 0.44996(12) 0.18535(7) 0.15062(10) 0.0176(3) Uani 1 1 d . . .
C6 C 0.27587(12) 0.19567(7) -0.05146(10) 0.0180(3) Uani 1 1 d . . .
N3 N 0.18787(10) -0.00400(6) 0.21189(8) 0.0193(2) Uani 1 1 d . . .
C7 C 0.15774(12) 0.17909(8) -0.14738(10) 0.0206(3) Uani 1 1 d . . .
H5 H 0.0849 0.1391 -0.1532 0.025 Uiso 1 1 calc R . .
C8 C 0.62014(12) 0.16893(7) 0.35370(10) 0.0185(3) Uani 1 1 d . . .
C9 C 0.27480(12) 0.06190(7) 0.19170(10) 0.0181(3) Uani 1 1 d . . .
C10 C 0.67380(13) 0.14046(8) 0.46468(10) 0.0219(3) Uani 1 1 d . . .
H6 H 0.6279 0.1017 0.4990 0.026 Uiso 1 1 calc R . .
C11 C 0.28642(13) 0.27968(8) -0.19163(10) 0.0203(3) Uani 1 1 d . . .
H7 H 0.3187 0.3207 -0.2319 0.024 Uiso 1 1 calc R . .
C12 C 0.83519(13) 0.23055(8) 0.43918(10) 0.0229(3) Uani 1 1 d . . .
H8 H 0.9188 0.2643 0.4513 0.027 Uiso 1 1 calc R . .
C13 C 0.80875(13) 0.17927(8) 0.51768(10) 0.0243(3) Uani 1 1 d . . .
H9 H 0.8703 0.1713 0.5941 0.029 Uiso 1 1 calc R . .
C14 C 0.16482(13) 0.23215(8) -0.23494(10) 0.0215(3) Uani 1 1 d . . .
H10 H 0.0975 0.2345 -0.3103 0.026 Uiso 1 1 calc R . .
N5 N 0.39948(11) 0.37532(7) 0.17767(9) 0.0244(3) Uani 1 1 d . . .
H21 H 0.4458 0.3368 0.1539 0.029 Uiso 1 1 calc R . .
C16 C 0.20445(14) 0.46842(9) 0.13883(11) 0.0282(3) Uani 1 1 d . . .
H11 H 0.1206 0.4920 0.0853 0.034 Uiso 1 1 calc R . .
C17 C 0.25098(14) 0.49542(8) 0.25383(11) 0.0258(3) Uani 1 1 d . . .
C18 C 0.44908(14) 0.40029(8) 0.28670(11) 0.0257(3) Uani 1 1 d . . .
H12 H 0.5347 0.3761 0.3372 0.031 Uiso 1 1 calc R . .
C21 C 0.38045(14) 0.45913(8) 0.32695(11) 0.0268(3) Uani 1 1 d . . .
H13 H 0.4191 0.4761 0.4044 0.032 Uiso 1 1 calc R . .
C22 C 0.27870(14) 0.40917(9) 0.10445(11) 0.0278(3) Uani 1 1 d . . .
H14 H 0.2449 0.3912 0.0272 0.033 Uiso 1 1 calc R . .
N4 N 0.17743(13) 0.55107(7) 0.29316(11) 0.0334(3) Uani 1 1 d . . .
C24 C 0.04582(16) 0.58945(10) 0.21832(16) 0.0430(4) Uani 1 1 d . . .
H15 H -0.0157 0.5495 0.1670 0.064 Uiso 1 1 calc R . .
H16 H 0.0747 0.6308 0.1728 0.064 Uiso 1 1 calc R . .
H17 H -0.0101 0.6138 0.2648 0.064 Uiso 1 1 calc R . .
C23 C 0.2360(2) 0.58119(10) 0.41016(14) 0.0483(4) Uani 1 1 d . . .
H18 H 0.3350 0.6031 0.4218 0.072 Uiso 1 1 calc R . .
H19 H 0.2414 0.5374 0.4645 0.072 Uiso 1 1 calc R . .
H20 H 0.1710 0.6232 0.4228 0.072 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 N3 1.2358(13) . ?
O1 C5 1.3052(15) . ?
O2 N3 1.2370(13) . ?
C1 C4 1.3853(17) . ?
C1 C9 1.3893(17) . ?
C1 H1 0.9500 . ?
N1 C12 1.3630(16) . ?
N1 C8 1.3756(16) . ?
N1 H2 0.8800 . ?
N2 C11 1.3594(16) . ?
N2 C6 1.3812(16) . ?
N2 H3 0.8800 . ?
C2 C3 1.3886(17) . ?
C2 C9 1.3865(17) . ?
C2 H4 0.9500 . ?
C3 C5 1.4389(17) . ?
C3 C6 1.4608(17) . ?
C4 C5 1.4395(17) . ?
C4 C8 1.4671(16) . ?
C6 C7 1.3834(17) . ?
N3 C9 1.4446(16) . ?
C7 C14 1.4101(17) . ?
C7 H5 0.9500 . ?
C8 C10 1.3826(17) . ?
C10 C13 1.4082(18) . ?
C10 H6 0.9500 . ?
C11 C14 1.3703(18) . ?
C11 H7 0.9500 . ?
C12 C13 1.3684(19) . ?
C12 H8 0.9500 . ?
C13 H9 0.9500 . ?
C14 H10 0.9500 . ?
N5 C18 1.3402(17) . ?
N5 C22 1.3476(17) . ?
N5 H21 0.8800 . ?
C16 C22 1.357(2) . ?
C16 C17 1.416(2) . ?
C16 H11 0.9500 . ?
C17 N4 1.3400(18) . ?
C17 C21 1.4193(19) . ?
C18 C21 1.3551(19) . ?
C18 H12 0.9500 . ?
C21 H13 0.9500 . ?
C22 H14 0.9500 . ?
N4 C24 1.456(2) . ?
N4 C23 1.460(2) . ?
C24 H15 0.9800 . ?
C24 H16 0.9800 . ?
C24 H17 0.9800 . ?
C23 H18 0.9800 . ?
C23 H19 0.9800 . ?
C23 H20 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
C4 C1 C9 120.01(11) . . ?
C4 C1 H1 120.0 . . ?
C9 C1 H1 120.0 . . ?
C12 N1 C8 110.09(10) . . ?
C12 N1 H2 125.0 . . ?
C8 N1 H2 125.0 . . ?
C11 N2 C6 110.02(10) . . ?
C11 N2 H3 125.0 . . ?
C6 N2 H3 125.0 . . ?
C3 C2 C9 119.89(11) . . ?
C3 C2 H4 120.1 . . ?
C9 C2 H4 120.1 . . ?
C2 C3 C5 119.82(11) . . ?
C2 C3 C6 118.77(10) . . ?
C5 C3 C6 121.40(11) . . ?
C1 C4 C5 119.76(10) . . ?
C1 C4 C8 118.85(10) . . ?
C5 C4 C8 121.38(11) . . ?
O1 C5 C3 121.10(10) . . ?
O1 C5 C4 120.40(10) . . ?
C3 C5 C4 118.50(10) . . ?
N2 C6 C7 106.66(10) . . ?
N2 C6 C3 122.87(10) . . ?
C7 C6 C3 130.47(11) . . ?
O3 N3 O2 122.30(10) . . ?
O3 N3 C9 119.01(9) . . ?
O2 N3 C9 118.68(9) . . ?
C6 C7 C14 107.72(11) . . ?
C6 C7 H5 126.1 . . ?
C14 C7 H5 126.1 . . ?
N1 C8 C10 106.69(10) . . ?
N1 C8 C4 122.95(10) . . ?
C10 C8 C4 130.34(11) . . ?
C2 C9 C1 121.99(11) . . ?
C2 C9 N3 119.06(10) . . ?
C1 C9 N3 118.90(10) . . ?
C8 C10 C13 107.76(11) . . ?
C8 C10 H6 126.1 . . ?
C13 C10 H6 126.1 . . ?
N2 C11 C14 108.01(11) . . ?
N2 C11 H7 126.0 . . ?
C14 C11 H7 126.0 . . ?
N1 C12 C13 107.82(11) . . ?
N1 C12 H8 126.1 . . ?
C13 C12 H8 126.1 . . ?
C12 C13 C10 107.64(11) . . ?
C12 C13 H9 126.2 . . ?
C10 C13 H9 126.2 . . ?
C11 C14 C7 107.59(11) . . ?
C11 C14 H10 126.2 . . ?
C7 C14 H10 126.2 . . ?
C18 N5 C22 120.07(12) . . ?
C18 N5 H21 120.0 . . ?
C22 N5 H21 120.0 . . ?
C22 C16 C17 120.53(12) . . ?
C22 C16 H11 119.7 . . ?
C17 C16 H11 119.7 . . ?
N4 C17 C16 122.75(12) . . ?
N4 C17 C21 121.24(12) . . ?
C16 C17 C21 116.01(12) . . ?
N5 C18 C21 121.81(12) . . ?
N5 C18 H12 119.1 . . ?
C21 C18 H12 119.1 . . ?
C18 C21 C17 120.22(12) . . ?
C18 C21 H13 119.9 . . ?
C17 C21 H13 119.9 . . ?
N5 C22 C16 121.31(12) . . ?
N5 C22 H14 119.3 . . ?
C16 C22 H14 119.3 . . ?
C17 N4 C24 121.57(13) . . ?
C17 N4 C23 120.57(13) . . ?
C24 N4 C23 117.55(13) . . ?
N4 C24 H15 109.5 . . ?
N4 C24 H16 109.5 . . ?
H15 C24 H16 109.5 . . ?
N4 C24 H17 109.5 . . ?
H15 C24 H17 109.5 . . ?
H16 C24 H17 109.5 . . ?
N4 C23 H18 109.5 . . ?
N4 C23 H19 109.5 . . ?
H18 C23 H19 109.5 . . ?
N4 C23 H20 109.5 . . ?
H18 C23 H20 109.5 . . ?
H19 C23 H20 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
C9 C2 C3 C5 1.23(17) . . . . ?
C9 C2 C3 C6 -178.41(10) . . . . ?
C9 C1 C4 C5 1.77(16) . . . . ?
C9 C1 C4 C8 -177.26(10) . . . . ?
C2 C3 C5 O1 -179.36(10) . . . . ?
C6 C3 C5 O1 0.28(17) . . . . ?
C2 C3 C5 C4 -0.24(16) . . . . ?
C6 C3 C5 C4 179.40(10) . . . . ?
C1 C4 C5 O1 177.86(10) . . . . ?
C8 C4 C5 O1 -3.13(16) . . . . ?
C1 C4 C5 C3 -1.27(16) . . . . ?
C8 C4 C5 C3 177.74(10) . . . . ?
C11 N2 C6 C7 -0.26(13) . . . . ?
C11 N2 C6 C3 179.49(10) . . . . ?
C2 C3 C6 N2 179.73(10) . . . . ?
C5 C3 C6 N2 0.08(17) . . . . ?
C2 C3 C6 C7 -0.59(19) . . . . ?
C5 C3 C6 C7 179.77(11) . . . . ?
N2 C6 C7 C14 0.02(13) . . . . ?
C3 C6 C7 C14 -179.70(11) . . . . ?
C12 N1 C8 C10 0.90(13) . . . . ?
C12 N1 C8 C4 -177.47(11) . . . . ?
C1 C4 C8 N1 175.86(10) . . . . ?
C5 C4 C8 N1 -3.16(17) . . . . ?
C1 C4 C8 C10 -2.09(19) . . . . ?
C5 C4 C8 C10 178.90(12) . . . . ?
C3 C2 C9 C1 -0.75(17) . . . . ?
C3 C2 C9 N3 -178.22(10) . . . . ?
C4 C1 C9 C2 -0.78(17) . . . . ?
C4 C1 C9 N3 176.69(10) . . . . ?
O3 N3 C9 C2 -175.63(10) . . . . ?
O2 N3 C9 C2 4.79(16) . . . . ?
O3 N3 C9 C1 6.82(16) . . . . ?
O2 N3 C9 C1 -172.76(10) . . . . ?
N1 C8 C10 C13 -0.62(13) . . . . ?
C4 C8 C10 C13 177.58(12) . . . . ?
C6 N2 C11 C14 0.41(13) . . . . ?
C8 N1 C12 C13 -0.81(14) . . . . ?
N1 C12 C13 C10 0.40(14) . . . . ?
C8 C10 C13 C12 0.14(14) . . . . ?
N2 C11 C14 C7 -0.39(14) . . . . ?
C6 C7 C14 C11 0.23(14) . . . . ?
C22 C16 C17 N4 -176.80(12) . . . . ?
C22 C16 C17 C21 2.32(18) . . . . ?
C22 N5 C18 C21 0.39(18) . . . . ?
N5 C18 C21 C17 1.00(19) . . . . ?
N4 C17 C21 C18 176.85(12) . . . . ?
C16 C17 C21 C18 -2.28(18) . . . . ?
C18 N5 C22 C16 -0.36(19) . . . . ?
C17 C16 C22 N5 -1.1(2) . . . . ?
C16 C17 N4 C24 -1.87(19) . . . . ?
C21 C17 N4 C24 179.06(12) . . . . ?
C16 C17 N4 C23 -175.36(12) . . . . ?
C21 C17 N4 C23 5.57(19) . . . . ?

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 H2 O1 0.88 2.06 2.6526(13) 123.4 .
N2 H3 O1 0.88 2.07 2.6573(13) 123.6 .
N5 H21 O1 0.88 1.81 2.6685(15) 165.9 .

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        66.99
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.038
