# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_1
_database_code_depnum_ccdc_archive 'CCDC 940757'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H26 N20 O7'
_chemical_formula_weight         802.73

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   26.008(3)
_cell_length_b                   6.8360(8)
_cell_length_c                   22.709(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 123.384(2)
_cell_angle_gamma                90.00
_cell_volume                     3371.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5744
_cell_measurement_theta_min      1.88
_cell_measurement_theta_max      27.080

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1656
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            15117
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         27.08
_reflns_number_total             3713
_reflns_number_gt                2662
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0920P)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     SHELXL
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3713
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1531
_refine_ls_wR_factor_gt          0.1266
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.015

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 0.37991(6) -0.00069(18) 1.18203(6) 0.0332(3) Uani 1 1 d . . .
H3 H 0.4047 0.0624 1.2178 0.050 Uiso 1 1 d R . .
N1 N 0.26105(6) 0.06560(18) 0.93246(7) 0.0205(3) Uani 1 1 d . . .
N2 N 0.23022(7) -0.10782(19) 0.91172(7) 0.0257(3) Uani 1 1 d . . .
N3 N 0.20469(7) 0.0800(2) 0.81608(7) 0.0267(3) Uani 1 1 d . . .
N4 N 0.26989(6) 0.3571(2) 0.88056(7) 0.0242(3) Uani 1 1 d . . .
N5 N 0.31081(6) 0.4232(2) 0.94328(7) 0.0249(3) Uani 1 1 d . . .
C1 C 0.19757(8) -0.0882(2) 0.84187(9) 0.0273(4) Uani 1 1 d . . .
H1 H 0.1711 -0.1860 0.8122 0.033 Uiso 1 1 calc R . .
C2 C 0.24533(7) 0.1770(2) 0.87500(8) 0.0222(4) Uani 1 1 d . . .
C3 C 0.32805(7) 0.3147(2) 1.00233(8) 0.0214(4) Uani 1 1 d . . .
C4 C 0.30365(7) 0.1272(2) 0.99985(8) 0.0204(4) Uani 1 1 d . . .
C5 C 0.32127(7) 0.0197(2) 1.05963(8) 0.0223(4) Uani 1 1 d . . .
H2 H 0.3047 -0.1035 1.0565 0.027 Uiso 1 1 calc R . .
C6 C 0.36459(8) 0.1021(2) 1.12460(8) 0.0238(4) Uani 1 1 d . . .
C7 C 0.39094(7) 0.2876(2) 1.12902(9) 0.0248(4) Uani 1 1 d . . .
H4 H 0.4206 0.3388 1.1729 0.030 Uiso 1 1 calc R . .
C8 C 0.37312(7) 0.3919(2) 1.06926(9) 0.0252(4) Uani 1 1 d . . .
H5 H 0.3906 0.5134 1.0726 0.030 Uiso 1 1 calc R . .
O2 O 0.13945(5) 0.74535(17) 0.67446(6) 0.0293(3) Uani 1 1 d . . .
H8 H 0.1730 0.6973 0.7065 0.044 Uiso 1 1 d R . .
N6 N 0.00647(6) 0.68578(19) 0.42405(7) 0.0217(3) Uani 1 1 d . . .
N7 N -0.02255(7) 0.8617(2) 0.40550(7) 0.0277(4) Uani 1 1 d . . .
N8 N -0.05274(7) 0.6763(2) 0.30843(7) 0.0311(4) Uani 1 1 d . . .
N9 N 0.01081(7) 0.3937(2) 0.36805(7) 0.0275(4) Uani 1 1 d . . .
N10 N 0.05234(6) 0.3241(2) 0.42972(7) 0.0265(3) Uani 1 1 d . . .
C9 C -0.05727(9) 0.8463(3) 0.33583(9) 0.0331(4) Uani 1 1 d . . .
H6 H -0.0833 0.9467 0.3074 0.040 Uiso 1 1 calc R . .
C10 C -0.01166(8) 0.5757(2) 0.36573(8) 0.0235(4) Uani 1 1 d . . .
C11 C 0.07205(7) 0.4304(2) 0.49035(8) 0.0219(4) Uani 1 1 d . . .
C12 C 0.04989(7) 0.6190(2) 0.49053(8) 0.0198(3) Uani 1 1 d . . .
C13 C 0.07101(7) 0.7251(2) 0.55187(8) 0.0216(4) Uani 1 1 d . . .
H7 H 0.0549 0.8476 0.5507 0.026 Uiso 1 1 calc R . .
C14 C 0.11703(7) 0.6415(2) 0.61496(8) 0.0218(4) Uani 1 1 d . . .
C15 C 0.13993(7) 0.4521(2) 0.61632(9) 0.0256(4) Uani 1 1 d . . .
H9 H 0.1703 0.3974 0.6592 0.031 Uiso 1 1 calc R . .
C16 C 0.11798(8) 0.3488(2) 0.55540(9) 0.0252(4) Uani 1 1 d . . .
H10 H 0.1334 0.2248 0.5570 0.030 Uiso 1 1 calc R . .
O3 O 0.0000 0.1237(3) 0.2500 0.0626(7) Uani 1 2 d S . .
H3A H 0.0063 0.2037 0.2812 0.094 Uiso 1 1 d R . .
O4 O 0.24944(5) 0.37388(16) 0.27477(5) 0.0280(3) Uani 1 1 d . . .
H4A H 0.2680 0.3993 0.2559 0.042 Uiso 1 1 d R . .
H4B H 0.2562 0.4658 0.3041 0.042 Uiso 1 1 d 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 C6 1.3348(19) . ?
O1 H3 0.8274 . ?
N1 N2 1.3618(18) . ?
N1 C2 1.3649(19) . ?
N1 C4 1.371(2) . ?
N2 C1 1.331(2) . ?
N3 C2 1.338(2) . ?
N3 C1 1.349(2) . ?
N4 N5 1.3026(18) . ?
N4 C2 1.361(2) . ?
N5 C3 1.374(2) . ?
C1 H1 0.9300 . ?
C3 C8 1.415(2) . ?
C3 C4 1.418(2) . ?
C4 C5 1.382(2) . ?
C5 C6 1.391(2) . ?
C5 H2 0.9300 . ?
C6 C7 1.418(2) . ?
C7 C8 1.368(2) . ?
C7 H4 0.9300 . ?
C8 H5 0.9300 . ?
O2 C14 1.3426(18) . ?
O2 H8 0.8371 . ?
N6 N7 1.3575(18) . ?
N6 C10 1.3620(19) . ?
N6 C12 1.3735(19) . ?
N7 C9 1.326(2) . ?
N8 C10 1.333(2) . ?
N8 C9 1.354(2) . ?
N9 N10 1.3001(19) . ?
N9 C10 1.363(2) . ?
N10 C11 1.382(2) . ?
C9 H6 0.9300 . ?
C11 C16 1.406(2) . ?
C11 C12 1.414(2) . ?
C12 C13 1.388(2) . ?
C13 C14 1.387(2) . ?
C13 H7 0.9300 . ?
C14 C15 1.418(2) . ?
C15 C16 1.367(2) . ?
C15 H9 0.9300 . ?
C16 H10 0.9300 . ?
O3 H3A 0.8376 . ?
O4 H4A 0.8216 . ?
O4 H4B 0.8611 . ?

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
C6 O1 H3 109.7 . . ?
N2 N1 C2 110.21(13) . . ?
N2 N1 C4 127.85(13) . . ?
C2 N1 C4 121.92(14) . . ?
C1 N2 N1 101.09(13) . . ?
C2 N3 C1 102.11(13) . . ?
N5 N4 C2 118.33(13) . . ?
N4 N5 C3 120.78(14) . . ?
N2 C1 N3 116.97(15) . . ?
N2 C1 H1 121.5 . . ?
N3 C1 H1 121.5 . . ?
N3 C2 N4 127.83(15) . . ?
N3 C2 N1 109.63(14) . . ?
N4 C2 N1 122.53(14) . . ?
N5 C3 C8 118.68(15) . . ?
N5 C3 C4 123.41(14) . . ?
C8 C3 C4 117.90(14) . . ?
N1 C4 C5 124.10(15) . . ?
N1 C4 C3 113.02(14) . . ?
C5 C4 C3 122.88(15) . . ?
C4 C5 C6 117.64(15) . . ?
C4 C5 H2 121.2 . . ?
C6 C5 H2 121.2 . . ?
O1 C6 C5 117.08(15) . . ?
O1 C6 C7 121.91(14) . . ?
C5 C6 C7 121.01(15) . . ?
C8 C7 C6 120.58(15) . . ?
C8 C7 H4 119.7 . . ?
C6 C7 H4 119.7 . . ?
C7 C8 C3 119.97(15) . . ?
C7 C8 H5 120.0 . . ?
C3 C8 H5 120.0 . . ?
C14 O2 H8 109.6 . . ?
N7 N6 C10 110.57(13) . . ?
N7 N6 C12 128.02(13) . . ?
C10 N6 C12 121.38(14) . . ?
C9 N7 N6 101.41(13) . . ?
C10 N8 C9 102.71(14) . . ?
N10 N9 C10 117.42(13) . . ?
N9 N10 C11 120.89(14) . . ?
N7 C9 N8 116.22(16) . . ?
N7 C9 H6 121.9 . . ?
N8 C9 H6 121.9 . . ?
N8 C10 N6 109.08(15) . . ?
N8 C10 N9 127.21(15) . . ?
N6 C10 N9 123.70(14) . . ?
N10 C11 C16 118.23(15) . . ?
N10 C11 C12 123.67(14) . . ?
C16 C11 C12 118.07(14) . . ?
N6 C12 C13 124.17(14) . . ?
N6 C12 C11 112.95(14) . . ?
C13 C12 C11 122.88(14) . . ?
C14 C13 C12 117.47(15) . . ?
C14 C13 H7 121.3 . . ?
C12 C13 H7 121.3 . . ?
O2 C14 C13 118.12(14) . . ?
O2 C14 C15 121.08(14) . . ?
C13 C14 C15 120.79(14) . . ?
C16 C15 C14 120.85(15) . . ?
C16 C15 H9 119.6 . . ?
C14 C15 H9 119.6 . . ?
C15 C16 C11 119.91(15) . . ?
C15 C16 H10 120.0 . . ?
C11 C16 H10 120.0 . . ?
H4A O4 H4B 108.8 . . ?

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
C2 N1 N2 C1 0.09(17) . . . . ?
C4 N1 N2 C1 -177.99(16) . . . . ?
C2 N4 N5 C3 -0.9(2) . . . . ?
N1 N2 C1 N3 0.2(2) . . . . ?
C2 N3 C1 N2 -0.4(2) . . . . ?
C1 N3 C2 N4 179.38(17) . . . . ?
C1 N3 C2 N1 0.46(18) . . . . ?
N5 N4 C2 N3 -177.45(15) . . . . ?
N5 N4 C2 N1 1.3(2) . . . . ?
N2 N1 C2 N3 -0.36(19) . . . . ?
C4 N1 C2 N3 177.85(13) . . . . ?
N2 N1 C2 N4 -179.35(14) . . . . ?
C4 N1 C2 N4 -1.1(2) . . . . ?
N4 N5 C3 C8 179.39(14) . . . . ?
N4 N5 C3 C4 0.3(2) . . . . ?
N2 N1 C4 C5 -1.9(3) . . . . ?
C2 N1 C4 C5 -179.75(15) . . . . ?
N2 N1 C4 C3 178.34(14) . . . . ?
C2 N1 C4 C3 0.5(2) . . . . ?
N5 C3 C4 N1 -0.1(2) . . . . ?
C8 C3 C4 N1 -179.16(14) . . . . ?
N5 C3 C4 C5 -179.86(15) . . . . ?
C8 C3 C4 C5 1.1(2) . . . . ?
N1 C4 C5 C6 -179.33(14) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 O1 178.10(14) . . . . ?
C4 C5 C6 C7 -1.8(2) . . . . ?
O1 C6 C7 C8 -178.26(15) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
C6 C7 C8 C3 0.0(3) . . . . ?
N5 C3 C8 C7 179.63(14) . . . . ?
C4 C3 C8 C7 -1.2(2) . . . . ?
C10 N6 N7 C9 0.27(18) . . . . ?
C12 N6 N7 C9 178.29(16) . . . . ?
C10 N9 N10 C11 0.9(2) . . . . ?
N6 N7 C9 N8 -0.2(2) . . . . ?
C10 N8 C9 N7 0.0(2) . . . . ?
C9 N8 C10 N6 0.15(19) . . . . ?
C9 N8 C10 N9 -178.63(18) . . . . ?
N7 N6 C10 N8 -0.3(2) . . . . ?
C12 N6 C10 N8 -178.46(14) . . . . ?
N7 N6 C10 N9 178.55(15) . . . . ?
C12 N6 C10 N9 0.4(3) . . . . ?
N10 N9 C10 N8 177.85(16) . . . . ?
N10 N9 C10 N6 -0.8(2) . . . . ?
N9 N10 C11 C16 -178.74(14) . . . . ?
N9 N10 C11 C12 -0.6(3) . . . . ?
N7 N6 C12 C13 1.1(3) . . . . ?
C10 N6 C12 C13 178.93(15) . . . . ?
N7 N6 C12 C11 -177.92(15) . . . . ?
C10 N6 C12 C11 -0.1(2) . . . . ?
N10 C11 C12 N6 0.2(2) . . . . ?
C16 C11 C12 N6 178.32(14) . . . . ?
N10 C11 C12 C13 -178.82(15) . . . . ?
C16 C11 C12 C13 -0.7(2) . . . . ?
N6 C12 C13 C14 -177.20(15) . . . . ?
C11 C12 C13 C14 1.7(2) . . . . ?
C12 C13 C14 O2 177.67(14) . . . . ?
C12 C13 C14 C15 -1.9(2) . . . . ?
O2 C14 C15 C16 -178.42(15) . . . . ?
C13 C14 C15 C16 1.1(3) . . . . ?
C14 C15 C16 C11 -0.1(3) . . . . ?
N10 C11 C16 C15 178.07(15) . . . . ?
C12 C11 C16 C15 -0.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        27.08
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.078
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_2
_database_code_depnum_ccdc_archive 'CCDC 940758'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Mn N10 O6'
_chemical_formula_weight         499.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   19.315(4)
_cell_length_b                   8.0880(16)
_cell_length_c                   11.970(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.203(9)
_cell_angle_gamma                90.00
_cell_volume                     1864.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3221
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1020
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8262
_exptl_absorpt_correction_T_max  0.9162
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            7279
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         27.64
_reflns_number_total             2176
_reflns_number_gt                1850
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0284P)²+1.8215P] 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     SHELXL
_refine_ls_extinction_coef       0.0011(1)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2152
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0641
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.017

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
Mn1 Mn 0.0000 0.35445(4) 0.2500 0.02168(11) Uani 1 2 d S . .
O1 O 0.45915(5) 0.32592(14) 0.08389(9) 0.0293(3) Uani 1 1 d . . .
O2 O -0.03006(6) 0.33108(15) 0.07290(9) 0.0330(3) Uani 1 1 d . . .
H2 H -0.0560 0.3856 0.0360 0.050 Uiso 1 1 d R . .
H3 H -0.0076 0.2800 0.0291 0.050 Uiso 1 1 d R . .
O3 O 0.0000 0.6158(2) 0.2500 0.0397(4) Uani 1 2 d S . .
H4 H -0.0117 0.6678 0.1968 0.060 Uiso 1 1 d R . .
O4 O 0.0000 0.0728(2) 0.2500 0.0326(4) Uani 1 2 d S . .
H6 H 0.0091 0.0141 0.3024 0.049 Uiso 1 1 d R . .
N3 N 0.11379(6) 0.33682(16) 0.21619(11) 0.0248(3) Uani 1 1 d . . .
N2 N 0.22119(6) 0.22528(16) 0.25425(10) 0.0245(3) Uani 1 1 d . . .
N1 N 0.22073(6) 0.33210(15) 0.16634(10) 0.0205(3) Uani 1 1 d . . .
N4 N 0.14161(6) 0.50730(16) 0.05859(11) 0.0265(3) Uani 1 1 d . . .
N5 N 0.19281(6) 0.54968(16) -0.00198(11) 0.0259(3) Uani 1 1 d . . .
C1 C 0.15599(8) 0.2350(2) 0.27984(13) 0.0256(3) Uani 1 1 d . . .
H1 H 0.1398 0.1748 0.3388 0.031 Uiso 1 1 calc R . .
C2 C 0.15640(7) 0.39829(18) 0.14319(12) 0.0217(3) Uani 1 1 d . . .
C3 C 0.25756(7) 0.48803(18) 0.01978(12) 0.0219(3) Uani 1 1 d . . .
C4 C 0.27623(7) 0.37428(17) 0.10695(12) 0.0206(3) Uani 1 1 d . . .
C5 C 0.34258(7) 0.31442(18) 0.12961(12) 0.0231(3) Uani 1 1 d . . .
H5 H 0.3524 0.2392 0.1874 0.028 Uiso 1 1 calc R . .
C6 C 0.39514(7) 0.36969(18) 0.06340(12) 0.0226(3) Uani 1 1 d . . .
C7 C 0.37648(8) 0.4821(2) -0.02650(13) 0.0259(3) Uani 1 1 d . . .
H7 H 0.4107 0.5166 -0.0721 0.031 Uiso 1 1 calc R . .
C8 C 0.31088(8) 0.54008(19) -0.04762(13) 0.0247(3) Uani 1 1 d . . .
H8 H 0.3009 0.6138 -0.1062 0.030 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
Mn1 O3 2.1140(17) . ?
Mn1 O2 2.1648(11) . ?
Mn1 O2 2.1648(11) 2 ?
Mn1 N3 2.2683(13) 2 ?
Mn1 N3 2.2683(13) . ?
Mn1 O4 2.2778(17) . ?
O1 C6 1.2921(18) . ?
O2 H2 0.7794 . ?
O2 H3 0.8167 . ?
O3 H4 0.7826 . ?
O4 H6 0.7962 . ?
N3 C2 1.3392(19) . ?
N3 C1 1.353(2) . ?
N2 C1 1.320(2) . ?
N2 N1 1.3610(17) . ?
N1 C2 1.3626(18) . ?
N1 C4 1.3721(18) . ?
N4 N5 1.3138(17) . ?
N4 C2 1.3572(19) . ?
N5 C3 1.3539(19) . ?
C1 H1 0.9300 . ?
C3 C4 1.418(2) . ?
C3 C8 1.418(2) . ?
C4 C5 1.378(2) . ?
C5 C6 1.406(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.434(2) . ?
C7 C8 1.357(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

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
O3 Mn1 O2 95.01(3) . . ?
O3 Mn1 O2 95.01(3) . 2 ?
O2 Mn1 O2 169.98(7) . 2 ?
O3 Mn1 N3 93.60(3) . 2 ?
O2 Mn1 N3 88.59(4) . 2 ?
O2 Mn1 N3 90.78(4) 2 2 ?
O3 Mn1 N3 93.60(3) . . ?
O2 Mn1 N3 90.78(4) . . ?
O2 Mn1 N3 88.59(4) 2 . ?
N3 Mn1 N3 172.79(7) 2 . ?
O3 Mn1 O4 180.0 . . ?
O2 Mn1 O4 84.99(3) . . ?
O2 Mn1 O4 84.99(3) 2 . ?
N3 Mn1 O4 86.40(3) 2 . ?
N3 Mn1 O4 86.40(3) . . ?
Mn1 O2 H2 128.3 . . ?
Mn1 O2 H3 123.8 . . ?
H2 O2 H3 105.8 . . ?
Mn1 O3 H4 122.5 . . ?
Mn1 O4 H6 126.6 . . ?
C2 N3 C1 102.69(12) . . ?
C2 N3 Mn1 137.98(10) . . ?
C1 N3 Mn1 119.29(10) . . ?
C1 N2 N1 100.92(12) . . ?
N2 N1 C2 111.15(11) . . ?
N2 N1 C4 126.68(12) . . ?
C2 N1 C4 122.17(12) . . ?
N5 N4 C2 117.10(12) . . ?
N4 N5 C3 121.31(13) . . ?
N2 C1 N3 116.81(13) . . ?
N2 C1 H1 121.6 . . ?
N3 C1 H1 121.6 . . ?
N3 C2 N4 128.48(13) . . ?
N3 C2 N1 108.44(12) . . ?
N4 C2 N1 123.08(13) . . ?
N5 C3 C4 124.20(13) . . ?
N5 C3 C8 118.71(13) . . ?
C4 C3 C8 117.08(13) . . ?
N1 C4 C5 124.15(14) . . ?
N1 C4 C3 112.11(13) . . ?
C5 C4 C3 123.74(13) . . ?
C4 C5 C6 118.48(14) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
O1 C6 C5 121.76(14) . . ?
O1 C6 C7 120.02(13) . . ?
C5 C6 C7 118.19(13) . . ?
C8 C7 C6 122.58(14) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C3 119.90(14) . . ?
C7 C8 H8 120.1 . . ?
C3 C8 H8 120.1 . . ?

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 Mn1 N3 C2 -51.28(15) . . . . ?
O2 Mn1 N3 C2 43.79(16) . . . . ?
O2 Mn1 N3 C2 -146.21(16) 2 . . . ?
N3 Mn1 N3 C2 128.72(15) 2 . . . ?
O4 Mn1 N3 C2 128.72(15) . . . . ?
O3 Mn1 N3 C1 131.58(11) . . . . ?
O2 Mn1 N3 C1 -133.35(12) . . . . ?
O2 Mn1 N3 C1 36.65(12) 2 . . . ?
N3 Mn1 N3 C1 -48.42(11) 2 . . . ?
O4 Mn1 N3 C1 -48.42(11) . . . . ?
C1 N2 N1 C2 -0.56(16) . . . . ?
C1 N2 N1 C4 178.46(14) . . . . ?
C2 N4 N5 C3 -0.5(2) . . . . ?
N1 N2 C1 N3 0.48(17) . . . . ?
C2 N3 C1 N2 -0.21(18) . . . . ?
Mn1 N3 C1 N2 177.83(10) . . . . ?
C1 N3 C2 N4 179.60(15) . . . . ?
Mn1 N3 C2 N4 2.2(3) . . . . ?
C1 N3 C2 N1 -0.17(16) . . . . ?
Mn1 N3 C2 N1 -177.61(11) . . . . ?
N5 N4 C2 N3 179.79(15) . . . . ?
N5 N4 C2 N1 -0.5(2) . . . . ?
N2 N1 C2 N3 0.48(17) . . . . ?
C4 N1 C2 N3 -178.59(13) . . . . ?
N2 N1 C2 N4 -179.30(13) . . . . ?
C4 N1 C2 N4 1.6(2) . . . . ?
N4 N5 C3 C4 0.4(2) . . . . ?
N4 N5 C3 C8 -179.19(13) . . . . ?
N2 N1 C4 C5 -1.0(2) . . . . ?
C2 N1 C4 C5 177.92(14) . . . . ?
N2 N1 C4 C3 179.48(13) . . . . ?
C2 N1 C4 C3 -1.60(19) . . . . ?
N5 C3 C4 N1 0.7(2) . . . . ?
C8 C3 C4 N1 -179.77(13) . . . . ?
N5 C3 C4 C5 -178.85(14) . . . . ?
C8 C3 C4 C5 0.7(2) . . . . ?
N1 C4 C5 C6 -178.97(13) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 O1 176.07(13) . . . . ?
C4 C5 C6 C7 -1.8(2) . . . . ?
O1 C6 C7 C8 -175.93(14) . . . . ?
C5 C6 C7 C8 1.9(2) . . . . ?
C6 C7 C8 C3 -0.7(2) . . . . ?
N5 C3 C8 C7 179.01(14) . . . . ?
C4 C3 C8 C7 -0.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.64
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_3
_database_code_depnum_ccdc_archive 'CCDC 940759'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 N10 O6 Zn'
_chemical_formula_weight         509.78

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   19.020(3)
_cell_length_b                   8.0801(12)
_cell_length_c                   11.9530(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.235(8)
_cell_angle_gamma                90.00
_cell_volume                     1832.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4169
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040.0
_exptl_absorpt_coefficient_mu    1.407
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7761
_exptl_absorpt_correction_T_max  0.8608
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            7256
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2116
_reflns_number_gt                1943
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0320P)²+1.4790P] 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     SHELXL
_refine_ls_extinction_coef       0.0017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2097
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0281
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0653
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.013

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
Zn1 Zn 0.0000 0.36107(3) 0.2500 0.02357(10) Uani 1 2 d S . .
O1 O 0.45914(6) 0.31972(16) 0.08224(10) 0.0301(3) Uani 1 1 d . . .
O2 O -0.02830(6) 0.33433(16) 0.07886(10) 0.0315(3) Uani 1 1 d . . .
O3 O 0.0000 0.6114(2) 0.2500 0.0382(4) Uani 1 2 d S . .
O4 O 0.0000 0.0737(2) 0.2500 0.0342(4) Uani 1 2 d S . .
N1 N 0.21752(7) 0.33271(15) 0.16823(10) 0.0198(3) Uani 1 1 d . . .
N2 N 0.21776(7) 0.22523(17) 0.25609(11) 0.0232(3) Uani 1 1 d . . .
N3 N 0.10913(7) 0.33660(16) 0.21873(11) 0.0232(3) Uani 1 1 d . . .
N4 N 0.13770(7) 0.50803(17) 0.06047(12) 0.0262(3) Uani 1 1 d . . .
N5 N 0.19003(7) 0.55018(17) -0.00053(11) 0.0255(3) Uani 1 1 d . . .
C1 C 0.15176(8) 0.2347(2) 0.28196(13) 0.0244(3) Uani 1 1 d . . .
H1 H 0.1354 0.1742 0.3409 0.029 Uiso 1 1 calc R . .
C2 C 0.15252(8) 0.39922(19) 0.14528(13) 0.0208(3) Uani 1 1 d . . .
C3 C 0.25546(8) 0.48825(19) 0.02114(13) 0.0217(3) Uani 1 1 d . . .
C4 C 0.27409(8) 0.37401(18) 0.10844(13) 0.0199(3) Uani 1 1 d . . .
C5 C 0.34093(8) 0.3127(2) 0.13044(13) 0.0232(3) Uani 1 1 d . . .
H5 H 0.3507 0.2375 0.1884 0.028 Uiso 1 1 calc R . .
C6 C 0.39462(8) 0.36625(19) 0.06314(13) 0.0232(3) Uani 1 1 d . . .
C7 C 0.37623(8) 0.4799(2) -0.02642(13) 0.0257(3) Uani 1 1 d . . .
H7 H 0.4110 0.5141 -0.0720 0.031 Uiso 1 1 calc R . .
C8 C 0.30982(8) 0.5393(2) -0.04685(13) 0.0246(3) Uani 1 1 d . . .
H8 H 0.2998 0.6135 -0.1054 0.029 Uiso 1 1 calc R . .
H2 H -0.0054 0.2839 0.0369 0.039(6) Uiso 1 1 d R . .
H3 H -0.0555 0.3911 0.0428 0.057(8) Uiso 1 1 d R . .
H4 H -0.0138 0.6609 0.1966 0.040(6) Uiso 1 1 d R . .
H6 H -0.0097 0.0142 0.1978 0.051(7) Uiso 1 1 d 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
Zn1 O3 2.0224(18) . ?
Zn1 O2 2.0877(12) . ?
Zn1 O2 2.0877(12) 2 ?
Zn1 N3 2.1452(13) 2 ?
Zn1 N3 2.1452(13) . ?
Zn1 O4 2.3218(19) . ?
O1 C6 1.2877(19) . ?
O2 H2 0.7996 . ?
O2 H3 0.7950 . ?
O3 H4 0.7821 . ?
O4 H6 0.7987 . ?
N1 C2 1.357(2) . ?
N1 N2 1.3625(18) . ?
N1 C4 1.3760(19) . ?
N2 C1 1.317(2) . ?
N3 C2 1.347(2) . ?
N3 C1 1.348(2) . ?
N4 N5 1.3212(18) . ?
N4 C2 1.356(2) . ?
N5 C3 1.349(2) . ?
C1 H1 0.9300 . ?
C3 C4 1.418(2) . ?
C3 C8 1.423(2) . ?
C4 C5 1.372(2) . ?
C5 C6 1.414(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.434(2) . ?
C7 C8 1.356(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

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
O3 Zn1 O2 95.94(4) . . ?
O3 Zn1 O2 95.94(4) . 2 ?
O2 Zn1 O2 168.12(7) . 2 ?
O3 Zn1 N3 95.29(4) . 2 ?
O2 Zn1 N3 88.76(5) . 2 ?
O2 Zn1 N3 90.14(5) 2 2 ?
O3 Zn1 N3 95.29(4) . . ?
O2 Zn1 N3 90.14(5) . . ?
O2 Zn1 N3 88.76(5) 2 . ?
N3 Zn1 N3 169.42(7) 2 . ?
O3 Zn1 O4 180.0 . . ?
O2 Zn1 O4 84.06(4) . . ?
O2 Zn1 O4 84.06(4) 2 . ?
N3 Zn1 O4 84.71(4) 2 . ?
N3 Zn1 O4 84.71(4) . . ?
Zn1 O2 H2 123.6 . . ?
Zn1 O2 H3 125.6 . . ?
H2 O2 H3 108.5 . . ?
Zn1 O3 H4 120.8 . . ?
Zn1 O4 H6 127.0 . . ?
C2 N1 N2 111.06(12) . . ?
C2 N1 C4 122.31(13) . . ?
N2 N1 C4 126.63(13) . . ?
C1 N2 N1 101.23(12) . . ?
C2 N3 C1 102.87(13) . . ?
C2 N3 Zn1 136.56(11) . . ?
C1 N3 Zn1 120.56(10) . . ?
N5 N4 C2 117.15(13) . . ?
N4 N5 C3 121.37(13) . . ?
N2 C1 N3 116.64(14) . . ?
N2 C1 H1 121.7 . . ?
N3 C1 H1 121.7 . . ?
N3 C2 N4 128.86(14) . . ?
N3 C2 N1 108.19(13) . . ?
N4 C2 N1 122.95(13) . . ?
N5 C3 C4 124.03(14) . . ?
N5 C3 C8 118.81(14) . . ?
C4 C3 C8 117.16(14) . . ?
C5 C4 N1 124.20(14) . . ?
C5 C4 C3 123.62(14) . . ?
N1 C4 C3 112.18(13) . . ?
C4 C5 C6 118.60(15) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
O1 C6 C5 121.93(15) . . ?
O1 C6 C7 119.73(14) . . ?
C5 C6 C7 118.31(14) . . ?
C8 C7 C6 122.25(14) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C3 120.05(15) . . ?
C7 C8 H8 120.0 . . ?
C3 C8 H8 120.0 . . ?

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
C2 N1 N2 C1 -0.54(17) . . . . ?
C4 N1 N2 C1 178.91(15) . . . . ?
O3 Zn1 N3 C2 -49.73(16) . . . . ?
O2 Zn1 N3 C2 46.25(16) . . . . ?
O2 Zn1 N3 C2 -145.58(16) 2 . . . ?
N3 Zn1 N3 C2 130.27(16) 2 . . . ?
O4 Zn1 N3 C2 130.27(16) . . . . ?
O3 Zn1 N3 C1 131.13(12) . . . . ?
O2 Zn1 N3 C1 -132.89(13) . . . . ?
O2 Zn1 N3 C1 35.28(13) 2 . . . ?
N3 Zn1 N3 C1 -48.87(12) 2 . . . ?
O4 Zn1 N3 C1 -48.87(12) . . . . ?
C2 N4 N5 C3 -0.4(2) . . . . ?
N1 N2 C1 N3 0.55(18) . . . . ?
C2 N3 C1 N2 -0.33(19) . . . . ?
Zn1 N3 C1 N2 179.06(11) . . . . ?
C1 N3 C2 N4 179.19(17) . . . . ?
Zn1 N3 C2 N4 0.0(3) . . . . ?
C1 N3 C2 N1 -0.04(17) . . . . ?
Zn1 N3 C2 N1 -179.28(11) . . . . ?
N5 N4 C2 N3 -179.79(16) . . . . ?
N5 N4 C2 N1 -0.7(2) . . . . ?
N2 N1 C2 N3 0.38(18) . . . . ?
C4 N1 C2 N3 -179.10(13) . . . . ?
N2 N1 C2 N4 -178.91(14) . . . . ?
C4 N1 C2 N4 1.6(2) . . . . ?
N4 N5 C3 C4 0.5(2) . . . . ?
N4 N5 C3 C8 -179.47(14) . . . . ?
C2 N1 C4 C5 178.45(15) . . . . ?
N2 N1 C4 C5 -0.9(2) . . . . ?
C2 N1 C4 C3 -1.4(2) . . . . ?
N2 N1 C4 C3 179.24(14) . . . . ?
N5 C3 C4 C5 -179.45(15) . . . . ?
C8 C3 C4 C5 0.5(2) . . . . ?
N5 C3 C4 N1 0.4(2) . . . . ?
C8 C3 C4 N1 -179.66(13) . . . . ?
N1 C4 C5 C6 -179.49(14) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 O1 176.78(15) . . . . ?
C4 C5 C6 C7 -1.2(2) . . . . ?
O1 C6 C7 C8 -176.72(15) . . . . ?
C5 C6 C7 C8 1.3(2) . . . . ?
C6 C7 C8 C3 -0.4(2) . . . . ?
N5 C3 C8 C7 179.53(15) . . . . ?
C4 C3 C8 C7 -0.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_4
_database_code_depnum_ccdc_archive 'CCDC 940760'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 Cd N10 O6'
_chemical_formula_weight         556.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   19.4542(7)
_cell_length_b                   8.1626(3)
_cell_length_c                   12.0696(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.203(2)
_cell_angle_gamma                90.00
_cell_volume                     1911.46(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6550
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.935
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    1.206
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7857
_exptl_absorpt_correction_T_max  0.8688
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            7866
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.71
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2194
_reflns_number_gt                2116
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0392P)²+2.6363P] 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     SHELXL
_refine_ls_extinction_coef       0.0011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2193
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0210
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd1 Cd 0.0000 0.14196(2) 0.2500 0.02182(10) Uani 1 2 d S . .
O1 O 0.45752(8) 0.1708(2) 0.08372(14) 0.0292(3) Uani 1 1 d . . .
O4 O 0.0000 -0.1300(3) 0.2500 0.0521(9) Uani 1 2 d S . .
H6 H -0.0127 -0.1785 0.1971 0.078 Uiso 1 1 d R . .
O2 O 0.03262(9) 0.1741(2) 0.43429(14) 0.0369(4) Uani 1 1 d . . .
H2 H 0.0583 0.1187 0.4697 0.055 Uiso 1 1 d R . .
H3 H 0.0087 0.2254 0.4721 0.055 Uiso 1 1 d R . .
O3 O 0.0000 0.4348(3) 0.2500 0.0364(5) Uani 1 2 d S . .
H4 H 0.0116 0.4874 0.3015 0.055 Uiso 1 1 d R . .
N3 N 0.11526(9) 0.1631(2) 0.21667(16) 0.0249(4) Uani 1 1 d . . .
N2 N 0.22154(9) 0.2727(2) 0.25422(14) 0.0243(4) Uani 1 1 d . . .
N1 N 0.22113(9) 0.1676(2) 0.16667(14) 0.0205(3) Uani 1 1 d . . .
N4 N 0.14235(9) -0.0059(2) 0.06015(16) 0.0278(4) Uani 1 1 d . . .
N5 N 0.19293(9) -0.0480(2) -0.00104(15) 0.0263(4) Uani 1 1 d . . .
C1 C 0.15694(11) 0.2636(3) 0.28015(18) 0.0260(4) Uani 1 1 d . . .
H1 H 0.1410 0.3230 0.3388 0.031 Uiso 1 1 calc R . .
C2 C 0.15734(10) 0.1019(3) 0.14400(17) 0.0224(4) Uani 1 1 d . . .
C3 C 0.25721(10) 0.0129(2) 0.02062(16) 0.0220(4) Uani 1 1 d . . .
C4 C 0.27583(11) 0.1255(2) 0.10706(17) 0.0202(4) Uani 1 1 d . . .
C5 C 0.34174(10) 0.1840(3) 0.12927(17) 0.0233(4) Uani 1 1 d . . .
H5 H 0.3517 0.2582 0.1867 0.028 Uiso 1 1 calc R . .
C6 C 0.39398(11) 0.1289(2) 0.06299(18) 0.0229(4) Uani 1 1 d . . .
C7 C 0.37524(11) 0.0183(3) -0.02695(17) 0.0257(4) Uani 1 1 d . . .
H7 H 0.4090 -0.0157 -0.0726 0.031 Uiso 1 1 calc R . .
C8 C 0.30987(11) -0.0383(3) -0.04750(17) 0.0259(4) Uani 1 1 d . . .
H8 H 0.2996 -0.1104 -0.1060 0.031 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
Cd1 O4 2.219(2) . ?
Cd1 O2 2.2831(16) . ?
Cd1 O2 2.2831(16) 2 ?
Cd1 N3 2.3134(18) . ?
Cd1 N3 2.3134(18) 2 ?
Cd1 O3 2.390(2) . ?
O1 C6 1.289(3) . ?
O4 H6 0.7760 . ?
O2 H2 0.7780 . ?
O2 H3 0.7955 . ?
O3 H4 0.7751 . ?
N3 C2 1.340(3) . ?
N3 C1 1.351(3) . ?
N2 C1 1.319(3) . ?
N2 N1 1.361(2) . ?
N1 C2 1.361(3) . ?
N1 C4 1.371(3) . ?
N4 N5 1.319(2) . ?
N4 C2 1.356(3) . ?
N5 C3 1.353(3) . ?
C1 H1 0.9300 . ?
C3 C4 1.417(3) . ?
C3 C8 1.423(3) . ?
C4 C5 1.376(3) . ?
C5 C6 1.412(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.438(3) . ?
C7 C8 1.359(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

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
O4 Cd1 O2 96.60(5) . . ?
O4 Cd1 O2 96.60(5) . 2 ?
O2 Cd1 O2 166.81(10) . 2 ?
O4 Cd1 N3 94.28(5) . . ?
O2 Cd1 N3 87.54(6) . . ?
O2 Cd1 N3 91.48(6) 2 . ?
O4 Cd1 N3 94.28(5) . 2 ?
O2 Cd1 N3 91.48(6) . 2 ?
O2 Cd1 N3 87.54(6) 2 2 ?
N3 Cd1 N3 171.43(9) . 2 ?
O4 Cd1 O3 180.0 . . ?
O2 Cd1 O3 83.40(5) . . ?
O2 Cd1 O3 83.40(5) 2 . ?
N3 Cd1 O3 85.72(5) . . ?
N3 Cd1 O3 85.72(5) 2 . ?
Cd1 O4 H6 120.7 . . ?
Cd1 O2 H2 126.2 . . ?
Cd1 O2 H3 119.2 . . ?
H2 O2 H3 111.7 . . ?
Cd1 O3 H4 123.7 . . ?
C2 N3 C1 103.17(17) . . ?
C2 N3 Cd1 137.09(15) . . ?
C1 N3 Cd1 119.72(14) . . ?
C1 N2 N1 101.37(16) . . ?
N2 N1 C2 110.98(17) . . ?
N2 N1 C4 127.21(17) . . ?
C2 N1 C4 121.79(17) . . ?
N5 N4 C2 117.29(17) . . ?
N4 N5 C3 120.86(18) . . ?
N2 C1 N3 116.24(18) . . ?
N2 C1 H1 121.9 . . ?
N3 C1 H1 121.9 . . ?
N3 C2 N4 128.49(19) . . ?
N3 C2 N1 108.24(18) . . ?
N4 C2 N1 123.27(19) . . ?
N5 C3 C4 124.27(19) . . ?
N5 C3 C8 118.35(18) . . ?
C4 C3 C8 117.38(18) . . ?
N1 C4 C5 123.97(19) . . ?
N1 C4 C3 112.48(18) . . ?
C5 C4 C3 123.55(19) . . ?
C4 C5 C6 118.56(19) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
O1 C6 C5 121.7(2) . . ?
O1 C6 C7 119.95(19) . . ?
C5 C6 C7 118.32(19) . . ?
C8 C7 C6 122.23(19) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C3 119.92(19) . . ?
C7 C8 H8 120.0 . . ?
C3 C8 H8 120.0 . . ?

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
O4 Cd1 N3 C2 50.9(2) . . . . ?
O2 Cd1 N3 C2 147.3(2) . . . . ?
O2 Cd1 N3 C2 -45.8(2) 2 . . . ?
N3 Cd1 N3 C2 -129.1(2) 2 . . . ?
O3 Cd1 N3 C2 -129.1(2) . . . . ?
O4 Cd1 N3 C1 -131.15(16) . . . . ?
O2 Cd1 N3 C1 -34.72(17) . . . . ?
O2 Cd1 N3 C1 132.12(17) 2 . . . ?
N3 Cd1 N3 C1 48.85(16) 2 . . . ?
O3 Cd1 N3 C1 48.85(16) . . . . ?
C1 N2 N1 C2 0.3(2) . . . . ?
C1 N2 N1 C4 -178.5(2) . . . . ?
C2 N4 N5 C3 0.8(3) . . . . ?
N1 N2 C1 N3 -0.4(2) . . . . ?
C2 N3 C1 N2 0.4(3) . . . . ?
Cd1 N3 C1 N2 -178.17(14) . . . . ?
C1 N3 C2 N4 -179.7(2) . . . . ?
Cd1 N3 C2 N4 -1.5(4) . . . . ?
C1 N3 C2 N1 -0.2(2) . . . . ?
Cd1 N3 C2 N1 178.01(15) . . . . ?
N5 N4 C2 N3 179.8(2) . . . . ?
N5 N4 C2 N1 0.4(3) . . . . ?
N2 N1 C2 N3 -0.1(2) . . . . ?
C4 N1 C2 N3 178.77(18) . . . . ?
N2 N1 C2 N4 179.44(19) . . . . ?
C4 N1 C2 N4 -1.7(3) . . . . ?
N4 N5 C3 C4 -0.8(3) . . . . ?
N4 N5 C3 C8 179.34(19) . . . . ?
N2 N1 C4 C5 1.1(3) . . . . ?
C2 N1 C4 C5 -177.59(19) . . . . ?
N2 N1 C4 C3 -179.72(18) . . . . ?
C2 N1 C4 C3 1.6(3) . . . . ?
N5 C3 C4 N1 -0.4(3) . . . . ?
C8 C3 C4 N1 179.41(18) . . . . ?
N5 C3 C4 C5 178.8(2) . . . . ?
C8 C3 C4 C5 -1.4(3) . . . . ?
N1 C4 C5 C6 178.84(18) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 O1 -175.56(19) . . . . ?
C4 C5 C6 C7 2.0(3) . . . . ?
O1 C6 C7 C8 175.4(2) . . . . ?
C5 C6 C7 C8 -2.2(3) . . . . ?
C6 C7 C8 C3 0.5(3) . . . . ?
N5 C3 C8 C7 -178.90(19) . . . . ?
C4 C3 C8 C7 1.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.098
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_5
_database_code_depnum_ccdc_archive 'CCDC 979363'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2014-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N10 O3'
_chemical_formula_weight         420.41

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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                   6.8792(11)
_cell_length_b                   20.841(3)
_cell_length_c                   13.359(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.471(12)
_cell_angle_gamma                90.00
_cell_volume                     1862.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1785
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      20.72

_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             872.0
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9649
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean none
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_number            16116
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0720
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         27.65
_reflns_number_total             4338
_reflns_number_gt                2150
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0885P)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     SHELXL
_refine_ls_extinction_coef       0.0008(1)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4338
_refine_ls_number_parameters     287
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1283
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1746
_refine_ls_wR_factor_gt          0.1391
_refine_ls_goodness_of_fit_ref   0.959
_refine_ls_restrained_S_all      0.959
_refine_ls_shift/su_max          0.047
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.3620(3) 0.24221(10) 0.89780(14) 0.0402(5) Uani 1 1 d . . .
N8 N 0.2634(3) 0.12607(10) 0.33933(15) 0.0428(5) Uani 1 1 d . . .
N4 N 0.3516(3) 0.19137(10) 0.83384(16) 0.0478(6) Uani 1 1 d . . .
N1 N 0.4159(3) 0.32460(11) 1.05764(16) 0.0493(6) Uani 1 1 d . . .
N9 N 0.2083(3) 0.12589(10) 0.23475(16) 0.0497(6) Uani 1 1 d . . .
N2 N 0.4588(3) 0.26471(11) 1.07828(16) 0.0500(6) Uani 1 1 d . . .
N5 N 0.4693(3) 0.16102(11) 1.00039(16) 0.0486(6) Uani 1 1 d . . .
N10 N 0.1975(3) 0.02505(11) 0.29853(18) 0.0563(7) Uani 1 1 d . . .
N7 N 0.2992(4) 0.05170(11) 0.47871(19) 0.0600(7) Uani 1 1 d . . .
N6 N 0.3559(4) 0.09883(12) 0.54300(18) 0.0592(7) Uani 1 1 d . . .
C4 C 0.3460(4) 0.34575(12) 0.95841(18) 0.0407(6) Uani 1 1 d . . .
C5 C 0.3140(3) 0.30452(11) 0.87242(19) 0.0374(6) Uani 1 1 d . . .
C7 C 0.4325(4) 0.22321(12) 0.99741(19) 0.0415(6) Uani 1 1 d . . .
C6 C 0.2381(4) 0.32621(12) 0.77306(18) 0.0411(6) Uani 1 1 d . . .
H4 H 0.2159 0.2981 0.7175 0.049 Uiso 1 1 calc R . .
C3 C 0.3019(4) 0.41098(13) 0.9408(2) 0.0495(7) Uani 1 1 d . . .
H3 H 0.3215 0.4393 0.9961 0.059 Uiso 1 1 calc R . .
C1 C 0.1968(4) 0.39045(12) 0.7591(2) 0.0440(6) Uani 1 1 d . . .
C2 C 0.2308(4) 0.43306(13) 0.8439(2) 0.0497(7) Uani 1 1 d . . .
H2 H 0.2041 0.4766 0.8330 0.060 Uiso 1 1 calc R . .
C8 C 0.4168(4) 0.14360(13) 0.8997(2) 0.0497(7) Uani 1 1 d . . .
C9 C 0.4274(5) 0.07708(15) 0.8631(3) 0.0741(10) Uani 1 1 d . . .
H6 H 0.3216 0.0522 0.8795 0.111 Uiso 1 1 calc R . .
H5 H 0.5540 0.0586 0.8961 0.111 Uiso 1 1 calc R . .
H7 H 0.4136 0.0772 0.7899 0.111 Uiso 1 1 calc R . .
C14 C 0.3241(3) 0.17719(12) 0.40334(19) 0.0408(6) Uani 1 1 d . . .
C13 C 0.3706(4) 0.16020(13) 0.50788(19) 0.0452(7) Uani 1 1 d . . .
C10 C 0.4088(4) 0.28596(13) 0.4431(2) 0.0444(6) Uani 1 1 d . . .
C15 C 0.3410(4) 0.23935(12) 0.36964(19) 0.0432(6) Uani 1 1 d . . .
H11 H 0.3078 0.2494 0.2999 0.052 Uiso 1 1 calc R . .
C16 C 0.2555(4) 0.06558(13) 0.3768(2) 0.0501(7) Uani 1 1 d . . .
C11 C 0.4566(4) 0.26969(14) 0.5487(2) 0.0518(7) Uani 1 1 d . . .
H9 H 0.5020 0.3014 0.5975 0.062 Uiso 1 1 calc R . .
C12 C 0.4373(4) 0.20882(15) 0.5801(2) 0.0531(7) Uani 1 1 d . . .
H10 H 0.4686 0.1992 0.6500 0.064 Uiso 1 1 calc R . .
C17 C 0.1700(4) 0.06342(13) 0.2153(2) 0.0529(7) Uani 1 1 d . . .
C18 C 0.1007(5) 0.04013(15) 0.1078(2) 0.0702(9) Uani 1 1 d . . .
H13 H -0.0428 0.0389 0.0896 0.105 Uiso 1 1 calc R . .
H12 H 0.1523 -0.0022 0.1023 0.105 Uiso 1 1 calc R . .
H14 H 0.1477 0.0686 0.0621 0.105 Uiso 1 1 calc R . .
O2 O 0.4349(3) 0.34753(9) 0.42186(14) 0.0619(6) Uani 1 1 d . . .
H8 H 0.4174 0.3521 0.3594 0.093 Uiso 1 1 calc R . .
O1 O 0.1239(3) 0.41721(9) 0.66630(14) 0.0587(6) Uani 1 1 d . . .
H1 H 0.0926 0.3889 0.6229 0.088 Uiso 1 1 calc R . .
O3 O 0.3609(4) 0.38852(12) 0.23659(17) 0.0917(9) Uani 1 1 d . . .
H15 H 0.3429 0.4269 0.2224 0.110(15) Uiso 1 1 d R . .
H16 H 0.3950 0.3710 0.1868 0.102(14) Uiso 1 1 d 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
N3 N4 1.353(3) . ?
N3 C5 1.363(3) . ?
N3 C7 1.365(3) . ?
N8 N9 1.360(3) . ?
N8 C16 1.363(3) . ?
N8 C14 1.369(3) . ?
N4 C8 1.335(3) . ?
N1 N2 1.297(3) . ?
N1 C4 1.373(3) . ?
N9 C17 1.342(3) . ?
N2 C7 1.363(3) . ?
N5 C7 1.319(3) . ?
N5 C8 1.358(3) . ?
N10 C16 1.331(3) . ?
N10 C17 1.346(4) . ?
N7 N6 1.303(3) . ?
N7 C16 1.355(4) . ?
N6 C13 1.374(4) . ?
C4 C3 1.401(4) . ?
C4 C5 1.410(3) . ?
C5 C6 1.384(3) . ?
C6 C1 1.372(4) . ?
C6 H4 0.9300 . ?
C3 C2 1.353(4) . ?
C3 H3 0.9300 . ?
C1 O1 1.345(3) . ?
C1 C2 1.416(4) . ?
C2 H2 0.9300 . ?
C8 C9 1.478(4) . ?
C9 H6 0.9600 . ?
C9 H5 0.9600 . ?
C9 H7 0.9600 . ?
C14 C15 1.385(3) . ?
C14 C13 1.403(3) . ?
C13 C12 1.401(4) . ?
C10 O2 1.335(3) . ?
C10 C15 1.382(3) . ?
C10 C11 1.413(4) . ?
C15 H11 0.9300 . ?
C11 C12 1.352(4) . ?
C11 H9 0.9300 . ?
C12 H10 0.9300 . ?
C17 C18 1.486(4) . ?
C18 H13 0.9600 . ?
C18 H12 0.9600 . ?
C18 H14 0.9600 . ?
O2 H8 0.8200 . ?
O1 H1 0.8200 . ?
O3 H15 0.8249 . ?
O3 H16 0.8390 . ?

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
N4 N3 C5 128.0(2) . . ?
N4 N3 C7 110.1(2) . . ?
C5 N3 C7 122.0(2) . . ?
N9 N8 C16 110.5(2) . . ?
N9 N8 C14 128.0(2) . . ?
C16 N8 C14 121.5(2) . . ?
C8 N4 N3 102.0(2) . . ?
N2 N1 C4 121.7(2) . . ?
C17 N9 N8 101.3(2) . . ?
N1 N2 C7 117.4(2) . . ?
C7 N5 C8 103.2(2) . . ?
C16 N10 C17 103.3(2) . . ?
N6 N7 C16 117.6(2) . . ?
N7 N6 C13 120.7(2) . . ?
N1 C4 C3 119.1(2) . . ?
N1 C4 C5 122.9(2) . . ?
C3 C4 C5 117.9(2) . . ?
N3 C5 C6 124.4(2) . . ?
N3 C5 C4 113.3(2) . . ?
C6 C5 C4 122.3(2) . . ?
N5 C7 N2 127.6(2) . . ?
N5 C7 N3 109.7(2) . . ?
N2 C7 N3 122.7(2) . . ?
C1 C6 C5 118.0(2) . . ?
C1 C6 H4 121.0 . . ?
C5 C6 H4 121.0 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
O1 C1 C6 123.4(2) . . ?
O1 C1 C2 115.7(2) . . ?
C6 C1 C2 120.8(2) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
N4 C8 N5 115.1(2) . . ?
N4 C8 C9 121.1(3) . . ?
N5 C8 C9 123.8(3) . . ?
C8 C9 H6 109.5 . . ?
C8 C9 H5 109.5 . . ?
H6 C9 H5 109.5 . . ?
C8 C9 H7 109.5 . . ?
H6 C9 H7 109.5 . . ?
H5 C9 H7 109.5 . . ?
N8 C14 C15 124.1(2) . . ?
N8 C14 C13 113.0(2) . . ?
C15 C14 C13 122.9(2) . . ?
N6 C13 C12 118.5(2) . . ?
N6 C13 C14 123.8(2) . . ?
C12 C13 C14 117.7(3) . . ?
O2 C10 C15 124.4(2) . . ?
O2 C10 C11 115.5(2) . . ?
C15 C10 C11 120.1(2) . . ?
C10 C15 C14 117.8(2) . . ?
C10 C15 H11 121.1 . . ?
C14 C15 H11 121.1 . . ?
N10 C16 N7 127.6(3) . . ?
N10 C16 N8 109.2(2) . . ?
N7 C16 N8 123.3(3) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H9 119.4 . . ?
C10 C11 H9 119.4 . . ?
C11 C12 C13 120.3(3) . . ?
C11 C12 H10 119.8 . . ?
C13 C12 H10 119.8 . . ?
N9 C17 N10 115.7(2) . . ?
N9 C17 C18 120.6(3) . . ?
N10 C17 C18 123.8(3) . . ?
C17 C18 H13 109.5 . . ?
C17 C18 H12 109.5 . . ?
H13 C18 H12 109.5 . . ?
C17 C18 H14 109.5 . . ?
H13 C18 H14 109.5 . . ?
H12 C18 H14 109.5 . . ?
C10 O2 H8 109.5 . . ?
C1 O1 H1 109.5 . . ?
H15 O3 H16 107.1 . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.65
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.048
