# 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 2017

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 796446'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 Cd N4 O5, C2 H6 O, 2(H2 O)'
_chemical_formula_sum            'C13 H22 Cd N4 O8'
_chemical_formula_weight         474.75

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'
Cd Cd -0.8075 1.2024 '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'

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                   12.8322(12)
_cell_length_b                   10.9479(10)
_cell_length_c                   12.9910(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.115(2)
_cell_angle_gamma                90.00
_cell_volume                     1806.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3529
_cell_measurement_theta_min      1.60
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    1.258
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_T_max  0.8338
_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10581
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3529
_reflns_number_gt                3281
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0271P)²+1.1725P] 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         3529
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0201
_refine_ls_wR_factor_ref         0.0540
_refine_ls_wR_factor_gt          0.0528
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.009
_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
Cd1 Cd 0.248831(10) 0.699166(12) 0.803213(11) 0.02498(6) Uani 1 1 d . . .
O1 O 0.62163(11) 0.32463(14) 0.60906(12) 0.0339(3) Uani 1 1 d . . .
O2 O 0.63889(11) 0.33886(14) 0.77945(11) 0.0324(3) Uani 1 1 d . . .
O3 O -0.12671(13) 0.35861(16) 0.74609(15) 0.0472(4) Uani 1 1 d . . .
O4 O -0.10340(13) 0.26122(16) 0.60432(13) 0.0462(4) Uani 1 1 d . . .
O5 O 0.26770(14) 0.55740(15) 0.93496(13) 0.0473(4) Uani 1 1 d . . .
H5X H 0.2201 0.5551 0.9710 0.057 Uiso 1 1 d R . .
H5Y H 0.2713 0.4850 0.9191 0.057 Uiso 1 1 d R . .
O6 O 0.50989(13) 0.24366(17) 0.91987(13) 0.0468(4) Uani 1 1 d . . .
H6X H 0.5520 0.2771 0.8820 0.056 Uiso 1 1 d R . .
H6Y H 0.5439 0.2207 0.9761 0.056 Uiso 1 1 d R . .
O7 O 0.8954(2) 0.4521(3) 0.9482(2) 0.1063(10) Uani 1 1 d . . .
H7X H 0.9057 0.4475 0.8874 0.159 Uiso 1 1 d R . .
H7Y H 0.9275 0.3960 0.9802 0.159 Uiso 1 1 d R . .
O8 O 0.30596(16) 0.31071(17) 0.90165(17) 0.0575(5) Uani 1 1 d . . .
H8X H 0.3750 0.2949 0.9130 0.069 Uiso 1 1 d R . .
N1 N 0.36582(12) 0.56285(14) 0.72321(12) 0.0250(3) Uani 1 1 d . . .
N2 N 0.33934(12) 0.51573(14) 0.62609(12) 0.0249(3) Uani 1 1 d . . .
N3 N 0.15120(12) 0.51211(15) 0.61322(13) 0.0270(3) Uani 1 1 d . . .
N4 N 0.12712(13) 0.57839(16) 0.69574(14) 0.0310(4) Uani 1 1 d . . .
C1 C 0.51564(18) 0.5520(2) 0.86268(17) 0.0388(5) Uani 1 1 d . . .
H1A H 0.4650 0.5741 0.9072 0.058 Uiso 1 1 calc R . .
H1B H 0.5608 0.6204 0.8552 0.058 Uiso 1 1 calc R . .
H1C H 0.5571 0.4845 0.8926 0.058 Uiso 1 1 calc R . .
C2 C 0.45969(14) 0.51620(17) 0.75856(15) 0.0249(4) Uani 1 1 d . . .
C3 C 0.49390(14) 0.43901(17) 0.68265(15) 0.0248(4) Uani 1 1 d . . .
C4 C 0.59060(14) 0.36394(17) 0.69136(15) 0.0251(4) Uani 1 1 d . . .
C5 C 0.41490(15) 0.44268(17) 0.59929(15) 0.0266(4) Uani 1 1 d . . .
H5 H 0.4141 0.4022 0.5363 0.032 Uiso 1 1 calc R . .
C6 C 0.24074(14) 0.55161(19) 0.56479(16) 0.0292(4) Uani 1 1 d . . .
H6A H 0.2362 0.5160 0.4959 0.035 Uiso 1 1 calc R . .
H6B H 0.2389 0.6398 0.5572 0.035 Uiso 1 1 calc R . .
C7 C 0.0973(2) 0.3251(2) 0.5085(2) 0.0431(5) Uani 1 1 d . . .
H7A H 0.1705 0.3058 0.5100 0.065 Uiso 1 1 calc R . .
H7B H 0.0701 0.3588 0.4418 0.065 Uiso 1 1 calc R . .
H7C H 0.0591 0.2523 0.5202 0.065 Uiso 1 1 calc R . .
C8 C 0.08534(15) 0.41594(18) 0.59120(15) 0.0276(4) Uani 1 1 d . . .
C9 C 0.01427(15) 0.42179(18) 0.66188(16) 0.0283(4) Uani 1 1 d . . .
C10 C -0.07706(15) 0.34138(19) 0.67082(17) 0.0315(4) Uani 1 1 d . . .
C11 C 0.04500(15) 0.52306(19) 0.72493(17) 0.0315(4) Uani 1 1 d . . .
H11 H 0.0116 0.5480 0.7804 0.038 Uiso 1 1 calc R . .
C12 C 0.2611(3) 0.2774(3) 0.8006(3) 0.0780(11) Uani 1 1 d . . .
H12A H 0.3014 0.3157 0.7516 0.094 Uiso 1 1 calc R . .
H12B H 0.1903 0.3105 0.7877 0.094 Uiso 1 1 calc R . .
C13 C 0.2555(3) 0.1474(4) 0.7790(3) 0.0857(11) Uani 1 1 d . . .
H13A H 0.2150 0.1081 0.8262 0.129 Uiso 1 1 calc R . .
H13B H 0.3253 0.1139 0.7876 0.129 Uiso 1 1 calc R . .
H13C H 0.2225 0.1343 0.7088 0.129 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 O5 2.2977(16) . ?
Cd1 O1 2.3267(15) 2_656 ?
Cd1 N4 2.3497(17) . ?
Cd1 O3 2.3727(16) 2_556 ?
Cd1 N1 2.4498(15) . ?
Cd1 O2 2.4505(14) 2_656 ?
Cd1 O4 2.4536(16) 2_556 ?
Cd1 C4 2.7319(19) 2_656 ?
Cd1 C10 2.758(2) 2_556 ?
O1 C4 1.268(2) . ?
O1 Cd1 2.3267(15) 2_646 ?
O2 C4 1.253(2) . ?
O2 Cd1 2.4505(14) 2_646 ?
O3 C10 1.254(3) . ?
O3 Cd1 2.3727(16) 2_546 ?
O4 C10 1.244(3) . ?
O4 Cd1 2.4536(16) 2_546 ?
O5 H5X 0.8203 . ?
O5 H5Y 0.8223 . ?
O6 H6X 0.8619 . ?
O6 H6Y 0.8351 . ?
O7 H7X 0.8200 . ?
O7 H7Y 0.8200 . ?
O8 C12 1.406(4) . ?
O8 H8X 0.8942 . ?
N1 C2 1.329(2) . ?
N1 N2 1.361(2) . ?
N2 C5 1.340(2) . ?
N2 C6 1.451(2) . ?
N3 C8 1.355(2) . ?
N3 N4 1.366(2) . ?
N3 C6 1.452(2) . ?
N4 C11 1.317(3) . ?
C1 C2 1.491(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.415(3) . ?
C3 C5 1.376(3) . ?
C3 C4 1.479(3) . ?
C4 Cd1 2.7319(18) 2_646 ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.488(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.384(3) . ?
C9 C11 1.402(3) . ?
C9 C10 1.483(3) . ?
C10 Cd1 2.758(2) 2_546 ?
C11 H11 0.9300 . ?
C12 C13 1.450(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
O5 Cd1 O1 92.35(6) . 2_656 ?
O5 Cd1 N4 93.09(7) . . ?
O1 Cd1 N4 172.84(6) 2_656 . ?
O5 Cd1 O3 133.96(6) . 2_556 ?
O1 Cd1 O3 95.56(6) 2_656 2_556 ?
N4 Cd1 O3 83.99(6) . 2_556 ?
O5 Cd1 N1 84.15(6) . . ?
O1 Cd1 N1 97.43(5) 2_656 . ?
N4 Cd1 N1 78.51(6) . . ?
O3 Cd1 N1 138.99(6) 2_556 . ?
O5 Cd1 O2 137.84(6) . 2_656 ?
O1 Cd1 O2 54.73(5) 2_656 2_656 ?
N4 Cd1 O2 118.25(6) . 2_656 ?
O3 Cd1 O2 80.17(5) 2_556 2_656 ?
N1 Cd1 O2 76.16(5) . 2_656 ?
O5 Cd1 O4 80.20(6) . 2_556 ?
O1 Cd1 O4 97.87(6) 2_656 2_556 ?
N4 Cd1 O4 87.65(6) . 2_556 ?
O3 Cd1 O4 53.80(6) 2_556 2_556 ?
N1 Cd1 O4 158.49(6) . 2_556 ?
O2 Cd1 O4 125.21(5) 2_656 2_556 ?
O5 Cd1 C4 115.28(6) . 2_656 ?
O1 Cd1 C4 27.56(6) 2_656 2_656 ?
N4 Cd1 C4 145.34(6) . 2_656 ?
O3 Cd1 C4 89.32(6) 2_556 2_656 ?
N1 Cd1 C4 84.73(5) . 2_656 ?
O2 Cd1 C4 27.28(5) 2_656 2_656 ?
O4 Cd1 C4 115.31(6) 2_556 2_656 ?
O5 Cd1 C10 106.99(6) . 2_556 ?
O1 Cd1 C10 97.75(6) 2_656 2_556 ?
N4 Cd1 C10 85.11(6) . 2_556 ?
O3 Cd1 C10 26.99(6) 2_556 2_556 ?
N1 Cd1 C10 160.73(6) . 2_556 ?
O2 Cd1 C10 103.34(6) 2_656 2_556 ?
O4 Cd1 C10 26.82(6) 2_556 2_556 ?
C4 Cd1 C10 103.71(6) 2_656 2_556 ?
C4 O1 Cd1 94.31(12) . 2_646 ?
C4 O2 Cd1 88.97(11) . 2_646 ?
C10 O3 Cd1 93.89(13) . 2_546 ?
C10 O4 Cd1 90.36(13) . 2_546 ?
Cd1 O5 H5X 115.9 . . ?
Cd1 O5 H5Y 118.0 . . ?
H5X O5 H5Y 100.7 . . ?
H6X O6 H6Y 109.6 . . ?
H7X O7 H7Y 107.7 . . ?
C12 O8 H8X 111.7 . . ?
C2 N1 N2 105.67(15) . . ?
C2 N1 Cd1 131.86(13) . . ?
N2 N1 Cd1 122.44(11) . . ?
C5 N2 N1 111.83(15) . . ?
C5 N2 C6 128.74(17) . . ?
N1 N2 C6 119.37(15) . . ?
C8 N3 N4 112.03(15) . . ?
C8 N3 C6 130.41(17) . . ?
N4 N3 C6 117.56(16) . . ?
C11 N4 N3 105.10(16) . . ?
C11 N4 Cd1 125.42(14) . . ?
N3 N4 Cd1 124.08(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 110.12(17) . . ?
N1 C2 C1 120.60(17) . . ?
C3 C2 C1 129.21(17) . . ?
C5 C3 C2 105.34(16) . . ?
C5 C3 C4 126.40(17) . . ?
C2 C3 C4 128.17(18) . . ?
O2 C4 O1 121.50(17) . . ?
O2 C4 C3 119.54(17) . . ?
O1 C4 C3 118.95(18) . . ?
O2 C4 Cd1 63.75(10) . 2_646 ?
O1 C4 Cd1 58.13(10) . 2_646 ?
C3 C4 Cd1 171.99(13) . 2_646 ?
N2 C5 C3 107.03(17) . . ?
N2 C5 H5 126.5 . . ?
C3 C5 H5 126.5 . . ?
N2 C6 N3 111.33(16) . . ?
N2 C6 H6A 109.4 . . ?
N3 C6 H6A 109.4 . . ?
N2 C6 H6B 109.4 . . ?
N3 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 105.89(17) . . ?
N3 C8 C7 123.15(18) . . ?
C9 C8 C7 130.92(19) . . ?
C8 C9 C11 105.48(17) . . ?
C8 C9 C10 128.79(19) . . ?
C11 C9 C10 125.73(19) . . ?
O4 C10 O3 121.95(19) . . ?
O4 C10 C9 120.29(19) . . ?
O3 C10 C9 117.8(2) . . ?
O4 C10 Cd1 62.83(11) . 2_546 ?
O3 C10 Cd1 59.13(11) . 2_546 ?
C9 C10 Cd1 176.87(16) . 2_546 ?
N4 C11 C9 111.48(18) . . ?
N4 C11 H11 124.3 . . ?
C9 C11 H11 124.3 . . ?
O8 C12 C13 116.0(3) . . ?
O8 C12 H12A 108.3 . . ?
C13 C12 H12A 108.3 . . ?
O8 C12 H12B 108.3 . . ?
C13 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O5 H5X O7 0.82 1.94 2.755(3) 178.0 3_667
O5 H5Y O8 0.82 1.98 2.790(3) 168.5 .
O6 H6X O2 0.86 1.97 2.830(2) 171.9 .
O6 H6Y O1 0.84 1.93 2.768(2) 177.3 4_566
O7 H7X O3 0.82 2.07 2.795(3) 147.5 1_655
O7 H7Y O4 0.82 2.43 3.092(4) 138.5 4_666
O8 H8X O6 0.89 1.81 2.696(3) 170.6 .
C1 H1C O2 0.96 2.50 3.098(3) 120.5 .
C7 H7C O4 0.96 2.49 3.095(3) 121.0 .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.057
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_t
_database_code_depnum_ccdc_archive 'CCDC 796445'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H14 Cd N4 O6'
_chemical_formula_weight         410.66

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'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   10.0760(17)
_cell_length_b                   10.2553(18)
_cell_length_c                   13.237(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1367.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2688
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      26.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.994
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_absorpt_coefficient_mu    1.634
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6398
_exptl_absorpt_correction_T_max  0.7574
_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8131
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.51
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2688
_reflns_number_gt                2613
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0347P)²+0.1805P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_number_reflns         2688
_refine_ls_number_parameters     201
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0556
_refine_ls_wR_factor_gt          0.0542
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_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
Cd1 Cd 0.457080(18) 0.650518(16) 1.005343(13) 0.02486(7) Uani 1 1 d . . .
O1 O 0.6661(2) 0.2343(2) 0.62334(16) 0.0374(5) Uani 1 1 d . . .
O2 O 0.4834(2) 0.3424(2) 0.59139(15) 0.0380(5) Uani 1 1 d . . .
O3 O 0.6945(2) 0.14031(19) 1.26891(15) 0.0364(5) Uani 1 1 d . . .
O4 O 0.5731(2) 0.2828(2) 1.35833(14) 0.0307(5) Uani 1 1 d . . .
O5 O 0.2833(2) 0.5171(2) 1.04835(15) 0.0352(5) Uani 1 1 d D . .
H5D H 0.2182 0.5157 1.0112 0.053 Uiso 1 1 d RD . .
H5C H 0.2603 0.5483 1.1027 0.053 Uiso 1 1 d RD . .
O6 O 0.0900(2) 0.4850(2) 0.90772(18) 0.0456(6) Uani 1 1 d D . .
H6D H 0.1391 0.4493 0.8668 0.068 Uiso 1 1 d RD . .
H6C H 0.0848 0.5548 0.8777 0.068 Uiso 1 1 d RD . .
N1 N 0.5679(2) 0.5374(2) 0.86648(16) 0.0271(5) Uani 1 1 d . . .
N2 N 0.6805(2) 0.4684(2) 0.88246(16) 0.0231(5) Uani 1 1 d . . .
N3 N 0.7027(2) 0.4523(2) 1.06186(15) 0.0222(4) Uani 1 1 d . . .
N4 N 0.5914(2) 0.5117(2) 1.09622(17) 0.0262(5) Uani 1 1 d . . .
C1 C 0.8182(3) 0.2894(3) 0.8121(2) 0.0350(7) Uani 1 1 d . . .
H1A H 0.8919 0.3305 0.8453 0.052 Uiso 1 1 calc R . .
H1B H 0.8432 0.2659 0.7446 0.052 Uiso 1 1 calc R . .
H1C H 0.7932 0.2124 0.8488 0.052 Uiso 1 1 calc R . .
C2 C 0.7043(3) 0.3810(2) 0.80867(19) 0.0225(5) Uani 1 1 d . . .
C3 C 0.6005(3) 0.3947(2) 0.74008(19) 0.0246(5) Uani 1 1 d . . .
C4 C 0.5822(3) 0.3194(3) 0.6459(2) 0.0264(6) Uani 1 1 d . . .
C5 C 0.5196(3) 0.4915(3) 0.77973(19) 0.0268(6) Uani 1 1 d . . .
H5 H 0.4416 0.5206 0.7496 0.032 Uiso 1 1 calc R . .
C6 C 0.7611(3) 0.5017(3) 0.96981(19) 0.0251(6) Uani 1 1 d . . .
H6A H 0.8493 0.4652 0.9616 0.030 Uiso 1 1 calc R . .
H6B H 0.7696 0.5957 0.9744 0.030 Uiso 1 1 calc R . .
C7 C 0.8589(3) 0.2728(3) 1.0990(2) 0.0377(7) Uani 1 1 d . . .
H7A H 0.8385 0.2072 1.0497 0.057 Uiso 1 1 calc R . .
H7B H 0.8885 0.2318 1.1602 0.057 Uiso 1 1 calc R . .
H7C H 0.9277 0.3286 1.0735 0.057 Uiso 1 1 calc R . .
C8 C 0.7390(3) 0.3510(3) 1.11991(18) 0.0236(5) Uani 1 1 d . . .
C9 C 0.6468(3) 0.3442(3) 1.19714(18) 0.0232(5) Uani 1 1 d . . .
C10 C 0.6398(3) 0.2484(3) 1.2808(2) 0.0257(6) Uani 1 1 d . . .
C11 C 0.5581(3) 0.4453(3) 1.17876(18) 0.0270(6) Uani 1 1 d . . .
H11 H 0.4849 0.4641 1.2190 0.032 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 O1 2.276(2) 3_656 ?
Cd1 O4 2.2777(19) 3_657 ?
Cd1 O5 2.294(2) . ?
Cd1 N4 2.303(2) . ?
Cd1 O2 2.423(2) 3_656 ?
Cd1 N1 2.444(2) . ?
Cd1 C4 2.676(3) 3_656 ?
O1 C4 1.251(4) . ?
O1 Cd1 2.276(2) 3_646 ?
O2 C4 1.251(4) . ?
O2 Cd1 2.423(2) 3_646 ?
O3 C10 1.248(3) . ?
O4 C10 1.276(3) . ?
O4 Cd1 2.2777(19) 3_647 ?
O5 H5D 0.8202 . ?
O5 H5C 0.8200 . ?
O6 H6D 0.8200 . ?
O6 H6C 0.8204 . ?
N1 C5 1.333(3) . ?
N1 N2 1.353(3) . ?
N2 C2 1.347(3) . ?
N2 C6 1.454(3) . ?
N3 C8 1.343(3) . ?
N3 N4 1.355(3) . ?
N3 C6 1.445(3) . ?
N4 C11 1.330(3) . ?
C1 C2 1.484(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.392(4) . ?
C3 C5 1.388(4) . ?
C3 C4 1.478(3) . ?
C4 Cd1 2.676(3) 3_646 ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.476(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.383(4) . ?
C9 C11 1.390(4) . ?
C9 C10 1.483(3) . ?
C11 H11 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
O1 Cd1 O4 107.19(8) 3_656 3_657 ?
O1 Cd1 O5 89.68(8) 3_656 . ?
O4 Cd1 O5 93.24(8) 3_657 . ?
O1 Cd1 N4 160.83(8) 3_656 . ?
O4 Cd1 N4 91.87(8) 3_657 . ?
O5 Cd1 N4 87.16(8) . . ?
O1 Cd1 O2 55.45(8) 3_656 3_656 ?
O4 Cd1 O2 88.17(7) 3_657 3_656 ?
O5 Cd1 O2 143.54(8) . 3_656 ?
N4 Cd1 O2 129.24(8) . 3_656 ?
O1 Cd1 N1 82.27(8) 3_656 . ?
O4 Cd1 N1 159.98(8) 3_657 . ?
O5 Cd1 N1 104.62(8) . . ?
N4 Cd1 N1 80.26(8) . . ?
O2 Cd1 N1 82.82(8) 3_656 . ?
O1 Cd1 C4 27.79(8) 3_656 3_656 ?
O4 Cd1 C4 100.80(8) 3_657 3_656 ?
O5 Cd1 C4 117.30(9) . 3_656 ?
N4 Cd1 C4 151.33(9) . 3_656 ?
O2 Cd1 C4 27.85(9) 3_656 3_656 ?
N1 Cd1 C4 79.18(8) . 3_656 ?
C4 O1 Cd1 94.21(17) . 3_646 ?
C4 O2 Cd1 87.40(17) . 3_646 ?
C10 O4 Cd1 122.87(18) . 3_647 ?
Cd1 O5 H5D 118.2 . . ?
Cd1 O5 H5C 101.6 . . ?
H5D O5 H5C 107.9 . . ?
H6D O6 H6C 96.2 . . ?
C5 N1 N2 104.9(2) . . ?
C5 N1 Cd1 130.41(19) . . ?
N2 N1 Cd1 120.91(16) . . ?
C2 N2 N1 112.6(2) . . ?
C2 N2 C6 129.3(2) . . ?
N1 N2 C6 118.0(2) . . ?
C8 N3 N4 112.4(2) . . ?
C8 N3 C6 130.0(2) . . ?
N4 N3 C6 117.5(2) . . ?
C11 N4 N3 104.7(2) . . ?
C11 N4 Cd1 126.7(2) . . ?
N3 N4 Cd1 126.09(16) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 C3 105.8(2) . . ?
N2 C2 C1 122.5(2) . . ?
C3 C2 C1 131.6(2) . . ?
C5 C3 C2 105.5(2) . . ?
C5 C3 C4 128.2(3) . . ?
C2 C3 C4 126.3(2) . . ?
O1 C4 O2 122.1(3) . . ?
O1 C4 C3 118.7(3) . . ?
O2 C4 C3 119.2(3) . . ?
O1 C4 Cd1 58.00(14) . 3_646 ?
O2 C4 Cd1 64.76(15) . 3_646 ?
C3 C4 Cd1 170.87(19) . 3_646 ?
N1 C5 C3 111.3(2) . . ?
N1 C5 H5 124.3 . . ?
C3 C5 H5 124.3 . . ?
N3 C6 N2 111.2(2) . . ?
N3 C6 H6A 109.4 . . ?
N2 C6 H6A 109.4 . . ?
N3 C6 H6B 109.4 . . ?
N2 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 106.2(2) . . ?
N3 C8 C7 122.4(2) . . ?
C9 C8 C7 131.4(3) . . ?
C8 C9 C11 105.4(2) . . ?
C8 C9 C10 128.1(2) . . ?
C11 C9 C10 126.5(2) . . ?
O3 C10 O4 125.4(2) . . ?
O3 C10 C9 118.3(2) . . ?
O4 C10 C9 116.3(2) . . ?
N4 C11 C9 111.3(2) . . ?
N4 C11 H11 124.3 . . ?
C9 C11 H11 124.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5C O3 0.82 2.00 2.738(3) 150.0 3_657
O5 H5D O6 0.82 1.91 2.714(3) 167.1 .
O6 H6C O4 0.82 2.32 2.967(3) 136.5 2_564
O6 H6D O3 0.82 2.09 2.868(3) 157.5 4_457
C1 H1B O1 0.96 2.42 2.986(4) 117.2 .
C6 H6A O6 0.97 2.54 3.419(4) 151.2 1_655
C6 H6B O4 0.97 2.53 3.139(3) 120.4 2_664
C11 H11 O3 0.93 2.56 3.311(4) 137.9 3_657

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.729
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1534605'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 N4 O4'
_chemical_formula_sum            'C11 H12 N4 O4'
_chemical_formula_weight         264.25

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   12.946(4)
_cell_length_b                   4.1020(13)
_cell_length_c                   24.925(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.773(13)
_cell_angle_gamma                90.00
_cell_volume                     1201.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1107
_cell_measurement_theta_min      3.166
_cell_measurement_theta_max      22.554

_exptl_crystal_description       stick
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_T_max  0.9798
_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7291
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0701
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         27.52
_reflns_number_total             2725
_reflns_number_gt                1493
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0980P)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         2725
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1789
_refine_ls_wR_factor_gt          0.1486
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_refine_ls_shift/su_max          0.004
_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 0.67902(15) -0.3021(5) 0.51803(8) 0.0536(6) Uani 1 1 d . . .
H1 H 0.6900 -0.3131 0.4880 0.080 Uiso 1 1 d R . .
O2 O 0.84350(15) -0.0304(5) 0.55100(8) 0.0578(6) Uani 1 1 d . . .
O3 O 0.89186(16) -0.2703(5) 0.96361(8) 0.0620(6) Uani 1 1 d . . .
H3 H 0.8765 -0.3115 0.9916 0.093 Uiso 1 1 d R . .
O4 O 0.72135(16) -0.0309(6) 0.92734(8) 0.0630(6) Uani 1 1 d . . .
N1 N 0.65654(17) 0.0857(5) 0.67065(8) 0.0391(5) Uani 1 1 d . . .
N2 N 0.76232(16) 0.2236(5) 0.68980(8) 0.0360(5) Uani 1 1 d . . .
N3 N 0.83213(16) 0.2388(5) 0.79556(8) 0.0358(5) Uani 1 1 d . . .
N4 N 0.93740(17) 0.0968(6) 0.82123(8) 0.0430(6) Uani 1 1 d . . .
C1 C 0.5312(2) -0.2296(7) 0.58494(11) 0.0508(7) Uani 1 1 d . . .
H1A H 0.4877 -0.2439 0.6080 0.076 Uiso 1 1 calc R . .
H1B H 0.5461 -0.4450 0.5749 0.076 Uiso 1 1 calc R . .
H1C H 0.4890 -0.1088 0.5494 0.076 Uiso 1 1 calc R . .
C2 C 0.6407(2) -0.0611(6) 0.61980(10) 0.0356(6) Uani 1 1 d . . .
C3 C 0.7356(2) -0.0141(6) 0.60699(9) 0.0353(6) Uani 1 1 d . . .
C4 C 0.7562(2) -0.1188(6) 0.55653(10) 0.0393(6) Uani 1 1 d . . .
C5 C 0.8113(2) 0.1694(6) 0.65296(10) 0.0378(6) Uani 1 1 d . . .
H5 H 0.8826 0.2415 0.6574 0.045 Uiso 1 1 calc R . .
C6 C 0.8039(2) 0.4240(6) 0.74234(9) 0.0396(6) Uani 1 1 d . . .
H6A H 0.8710 0.5410 0.7450 0.048 Uiso 1 1 calc R . .
H6B H 0.7463 0.5838 0.7390 0.048 Uiso 1 1 calc R . .
C7 C 0.6502(2) 0.3183(8) 0.80710(12) 0.0522(7) Uani 1 1 d . . .
H7A H 0.6518 0.5348 0.8221 0.078 Uiso 1 1 calc R . .
H7B H 0.6086 0.1774 0.8218 0.078 Uiso 1 1 calc R . .
H7C H 0.6137 0.3220 0.7647 0.078 Uiso 1 1 calc R . .
C8 C 0.7694(2) 0.1943(6) 0.82702(10) 0.0356(6) Uani 1 1 d . . .
C9 C 0.8373(2) 0.0123(6) 0.87553(10) 0.0379(6) Uani 1 1 d . . .
C10 C 0.8124(2) -0.0994(7) 0.92460(10) 0.0412(6) Uani 1 1 d . . .
C11 C 0.9391(2) -0.0402(7) 0.86945(10) 0.0420(6) Uani 1 1 d . . .
H11 H 1.0005 -0.1577 0.8963 0.050 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 C4 1.297(3) . ?
O1 H1 0.8201 . ?
O2 C4 1.248(3) . ?
O3 C10 1.287(3) . ?
O3 H3 0.8200 . ?
O4 C10 1.241(3) . ?
N1 C2 1.339(3) . ?
N1 N2 1.369(3) . ?
N2 C5 1.335(3) . ?
N2 C6 1.445(3) . ?
N3 C8 1.357(3) . ?
N3 N4 1.369(3) . ?
N3 C6 1.436(3) . ?
N4 C11 1.319(3) . ?
C1 C2 1.487(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.407(3) . ?
C3 C5 1.378(3) . ?
C3 C4 1.456(3) . ?
C5 H5 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.499(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.379(3) . ?
C9 C11 1.406(3) . ?
C9 C10 1.463(3) . ?
C11 H11 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
C4 O1 H1 109.4 . . ?
C10 O3 H3 110.7 . . ?
C2 N1 N2 104.49(18) . . ?
C5 N2 N1 112.66(19) . . ?
C5 N2 C6 127.9(2) . . ?
N1 N2 C6 119.29(19) . . ?
C8 N3 N4 113.09(18) . . ?
C8 N3 C6 128.5(2) . . ?
N4 N3 C6 118.32(19) . . ?
C11 N4 N3 103.92(18) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 110.6(2) . . ?
N1 C2 C1 119.5(2) . . ?
C3 C2 C1 129.9(2) . . ?
C5 C3 C2 105.7(2) . . ?
C5 C3 C4 123.8(2) . . ?
C2 C3 C4 130.5(2) . . ?
O2 C4 O1 122.7(2) . . ?
O2 C4 C3 120.8(2) . . ?
O1 C4 C3 116.5(2) . . ?
N2 C5 C3 106.6(2) . . ?
N2 C5 H5 126.7 . . ?
C3 C5 H5 126.7 . . ?
N3 C6 N2 113.0(2) . . ?
N3 C6 H6A 109.0 . . ?
N2 C6 H6A 109.0 . . ?
N3 C6 H6B 109.0 . . ?
N2 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 105.3(2) . . ?
N3 C8 C7 123.1(2) . . ?
C9 C8 C7 131.6(2) . . ?
C8 C9 C11 105.7(2) . . ?
C8 C9 C10 128.4(2) . . ?
C11 C9 C10 126.0(2) . . ?
O4 C10 O3 124.0(2) . . ?
O4 C10 C9 121.4(2) . . ?
O3 C10 C9 114.6(2) . . ?
N4 C11 C9 112.0(2) . . ?
N4 C11 H11 124.0 . . ?
C9 C11 H11 124.0 . . ?

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 C5 0.3(3) . . . . ?
C2 N1 N2 C6 175.6(2) . . . . ?
C8 N3 N4 C11 0.4(3) . . . . ?
C6 N3 N4 C11 177.4(2) . . . . ?
N2 N1 C2 C3 -0.3(3) . . . . ?
N2 N1 C2 C1 -177.9(2) . . . . ?
N1 C2 C3 C5 0.2(3) . . . . ?
C1 C2 C3 C5 177.5(3) . . . . ?
N1 C2 C3 C4 -178.2(2) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C5 C3 C4 O2 -3.8(4) . . . . ?
C2 C3 C4 O2 174.3(3) . . . . ?
C5 C3 C4 O1 177.2(2) . . . . ?
C2 C3 C4 O1 -4.7(4) . . . . ?
N1 N2 C5 C3 -0.2(3) . . . . ?
C6 N2 C5 C3 -175.1(2) . . . . ?
C2 C3 C5 N2 0.0(3) . . . . ?
C4 C3 C5 N2 178.5(2) . . . . ?
C8 N3 C6 N2 -99.4(3) . . . . ?
N4 N3 C6 N2 84.1(3) . . . . ?
C5 N2 C6 N3 -114.1(3) . . . . ?
N1 N2 C6 N3 71.3(3) . . . . ?
N4 N3 C8 C9 -0.3(3) . . . . ?
C6 N3 C8 C9 -177.0(2) . . . . ?
N4 N3 C8 C7 -178.2(2) . . . . ?
C6 N3 C8 C7 5.2(4) . . . . ?
N3 C8 C9 C11 0.1(3) . . . . ?
C7 C8 C9 C11 177.7(3) . . . . ?
N3 C8 C9 C10 178.6(2) . . . . ?
C7 C8 C9 C10 -3.8(5) . . . . ?
C8 C9 C10 O4 -1.0(5) . . . . ?
C11 C9 C10 O4 177.2(3) . . . . ?
C8 C9 C10 O3 179.1(3) . . . . ?
C11 C9 C10 O3 -2.6(4) . . . . ?
N3 N4 C11 C9 -0.3(3) . . . . ?
C8 C9 C11 N4 0.2(3) . . . . ?
C10 C9 C11 N4 -178.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.218
_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/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_t
_database_code_depnum_ccdc_archive 'CCDC 1534608'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 N4 O6 Zn, 2(H O0.50)'
_chemical_formula_sum            'C11 H16 N4 O7 Zn'
_chemical_formula_weight         381.65

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           Orthorhombic
_symmetry_space_group_name_H-M   Pnma
_symmetry_space_group_name_Hall  '-P 2ac 2n'

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

_cell_length_a                   12.3977(11)
_cell_length_b                   12.6699(12)
_cell_length_c                   9.4124(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1478.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2598
_cell_measurement_theta_min      2.696
_cell_measurement_theta_max      26.958

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    1.705
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6850
_exptl_absorpt_correction_T_max  0.7267
_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9122
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         27.65
_reflns_number_total             1771
_reflns_number_gt                1501
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0687P)²+4.2968P] 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         1771
_refine_ls_number_parameters     115
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1446
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.212
_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
C1 C -0.0646(4) 1.0922(4) 0.2379(6) 0.0369(11) Uani 1 1 d . . .
H1A H -0.1000 1.1592 0.2473 0.055 Uiso 1 1 calc R . .
H1B H -0.1151 1.0366 0.2576 0.055 Uiso 1 1 calc R . .
H1C H -0.0377 1.0846 0.1428 0.055 Uiso 1 1 calc R . .
C2 C 0.0266(3) 1.0862(3) 0.3399(4) 0.0233(8) Uani 1 1 d . . .
C3 C 0.1114(3) 1.0151(3) 0.3501(4) 0.0236(8) Uani 1 1 d . . .
C4 C 0.1344(3) 0.9238(3) 0.2563(4) 0.0234(8) Uani 1 1 d . . .
C5 C 0.1729(4) 1.0492(3) 0.4661(5) 0.0260(9) Uani 1 1 d . . .
H5 H 0.2357 1.0162 0.4970 0.031 Uiso 1 1 calc R . .
C6 C -0.0197(5) 1.2500 0.4825(7) 0.0233(12) Uani 1 2 d S . .
H6A H -0.0358 1.2500 0.5833 0.028 Uiso 1 2 calc SR . .
H6B H -0.0875 1.2500 0.4311 0.028 Uiso 1 2 calc SR . .
N1 N 0.1308(3) 1.1338(3) 0.5262(4) 0.0247(7) Uani 1 1 d . . .
N2 N 0.0409(3) 1.1560(3) 0.4468(4) 0.0221(7) Uani 1 1 d . . .
O1 O 0.2201(2) 0.8737(2) 0.2794(4) 0.0305(7) Uani 1 1 d . . .
O2 O 0.0675(3) 0.9033(3) 0.1589(4) 0.0368(8) Uani 1 1 d . . .
O3 O 0.4104(4) 0.7500 0.3165(5) 0.0321(10) Uani 1 2 d SD . .
H3X H 0.4459 0.6943 0.3183 0.048 Uiso 1 1 d RD . .
O4 O 0.1624(4) 0.7500 0.0147(5) 0.0289(9) Uani 1 2 d SD . .
H4X H 0.1240 0.7002 0.0549 0.043 Uiso 1 1 d RD . .
O5 O 0.2210(10) 0.2099(13) 0.0894(14) 0.132(9) Uani 0.50 1 d PD . .
H5Y H 0.1835 0.2019 0.0107 0.197 Uiso 0.50 1 d PRD . .
H5X H 0.2229 0.1785 0.1861 0.197 Uiso 0.50 1 d PRD . .
Zn1 Zn 0.28750(5) 0.7500 0.16226(7) 0.0222(2) Uani 1 2 d S . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.485(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N2 1.351(5) . ?
C2 C3 1.388(6) . ?
C3 C5 1.400(6) . ?
C3 C4 1.482(5) . ?
C4 O1 1.257(5) . ?
C4 O2 1.263(5) . ?
C5 N1 1.320(5) . ?
C5 H5 0.9300 . ?
C6 N2 1.448(5) . ?
C6 N2 1.448(5) 8_585 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N1 N2 1.371(5) . ?
N1 Zn1 2.199(3) 2_575 ?
O1 Zn1 2.090(3) . ?
O3 Zn1 2.105(4) . ?
O3 H3X 0.8317 . ?
O4 Zn1 2.082(4) . ?
O4 H4X 0.8762 . ?
O5 O5 1.02(3) 8_565 ?
O5 H5Y 0.8808 . ?
O5 H5X 0.9932 . ?
Zn1 O1 2.090(3) 8_575 ?
Zn1 N1 2.199(3) 7_655 ?
Zn1 N1 2.199(3) 2_574 ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 C3 105.9(4) . . ?
N2 C2 C1 123.2(4) . . ?
C3 C2 C1 130.9(4) . . ?
C2 C3 C5 105.4(4) . . ?
C2 C3 C4 127.6(4) . . ?
C5 C3 C4 126.9(4) . . ?
O1 C4 O2 125.2(4) . . ?
O1 C4 C3 117.0(4) . . ?
O2 C4 C3 117.8(4) . . ?
N1 C5 C3 111.7(4) . . ?
N1 C5 H5 124.2 . . ?
C3 C5 H5 124.2 . . ?
N2 C6 N2 110.8(5) . 8_585 ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6A 109.5 8_585 . ?
N2 C6 H6B 109.5 . . ?
N2 C6 H6B 109.5 8_585 . ?
H6A C6 H6B 108.1 . . ?
C5 N1 N2 104.8(3) . . ?
C5 N1 Zn1 127.7(3) . 2_575 ?
N2 N1 Zn1 123.7(2) . 2_575 ?
C2 N2 N1 112.2(3) . . ?
C2 N2 C6 130.0(4) . . ?
N1 N2 C6 117.7(4) . . ?
C4 O1 Zn1 128.7(3) . . ?
Zn1 O3 H3X 113.4 . . ?
Zn1 O4 H4X 96.7 . . ?
O5 O5 H5Y 96.6 8_565 . ?
O5 O5 H5X 113.6 8_565 . ?
H5Y O5 H5X 137.5 . . ?
O4 Zn1 O1 93.11(12) . 8_575 ?
O4 Zn1 O1 93.11(12) . . ?
O1 Zn1 O1 97.12(19) 8_575 . ?
O4 Zn1 O3 178.23(18) . . ?
O1 Zn1 O3 85.72(12) 8_575 . ?
O1 Zn1 O3 85.72(12) . . ?
O4 Zn1 N1 87.41(14) . 7_655 ?
O1 Zn1 N1 89.39(13) 8_575 7_655 ?
O1 Zn1 N1 173.44(13) . 7_655 ?
O3 Zn1 N1 93.91(14) . 7_655 ?
O4 Zn1 N1 87.41(14) . 2_574 ?
O1 Zn1 N1 173.44(13) 8_575 2_574 ?
O1 Zn1 N1 89.39(13) . 2_574 ?
O3 Zn1 N1 93.91(14) . 2_574 ?
N1 Zn1 N1 84.10(18) 7_655 2_574 ?

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
N2 C2 C3 C5 -0.4(5) . . . . ?
C1 C2 C3 C5 179.5(5) . . . . ?
N2 C2 C3 C4 -178.9(4) . . . . ?
C1 C2 C3 C4 1.0(8) . . . . ?
C2 C3 C4 O1 175.4(4) . . . . ?
C5 C3 C4 O1 -2.8(6) . . . . ?
C2 C3 C4 O2 -3.8(6) . . . . ?
C5 C3 C4 O2 178.0(4) . . . . ?
C2 C3 C5 N1 0.7(5) . . . . ?
C4 C3 C5 N1 179.2(4) . . . . ?
C3 C5 N1 N2 -0.7(5) . . . . ?
C3 C5 N1 Zn1 -158.9(3) . . . 2_575 ?
C3 C2 N2 N1 -0.1(5) . . . . ?
C1 C2 N2 N1 -179.9(4) . . . . ?
C3 C2 N2 C6 176.3(4) . . . . ?
C1 C2 N2 C6 -3.6(7) . . . . ?
C5 N1 N2 C2 0.5(4) . . . . ?
Zn1 N1 N2 C2 159.7(3) 2_575 . . . ?
C5 N1 N2 C6 -176.3(4) . . . . ?
Zn1 N1 N2 C6 -17.1(5) 2_575 . . . ?
N2 C6 N2 C2 -106.7(5) 8_585 . . . ?
N2 C6 N2 N1 69.4(6) 8_585 . . . ?
O2 C4 O1 Zn1 4.8(6) . . . . ?
C3 C4 O1 Zn1 -174.4(3) . . . . ?
C4 O1 Zn1 O4 -0.6(4) . . . . ?
C4 O1 Zn1 O1 -94.1(4) . . . 8_575 ?
C4 O1 Zn1 O3 -179.2(4) . . . . ?
C4 O1 Zn1 N1 93.8(12) . . . 7_655 ?
C4 O1 Zn1 N1 86.8(4) . . . 2_574 ?

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
C6 H6B O5 0.97 2.44 3.325(13) 152.2 6_566
C6 H6B O5 0.97 2.44 3.325(13) 152.2 3_465
O4 H4X O2 0.88 1.78 2.645(4) 169.0 8_575
O3 H3X O2 0.83 1.96 2.760(5) 160.6 3_565

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        27.65
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         2.060
_refine_diff_density_min         -1.390
_refine_diff_density_rms         0.111
####################################################################### 
# 
# 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_mo_120514o_0m
_database_code_depnum_ccdc_archive 'CCDC 1534607'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N5 O6 Zn'
_chemical_formula_sum            'C14 H19 N5 O6 Zn'
_chemical_formula_weight         418.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   8.577(4)
_cell_length_b                   9.448(5)
_cell_length_c                   22.037(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1785.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    1735
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      23.82

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    1.417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7096
_exptl_absorpt_correction_T_max  0.7648
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9922
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0610
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3515
_reflns_number_gt                3077
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.07P)²+1.99P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_number_reflns         3515
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.1404
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
C1 C 0.5052(6) -0.1029(6) 0.2300(3) 0.0279(12) Uani 1 1 d . . .
H1A H 0.4917 -0.2020 0.2219 0.042 Uiso 1 1 calc R . .
H1B H 0.4132 -0.0525 0.2178 0.042 Uiso 1 1 calc R . .
H1C H 0.5226 -0.0891 0.2726 0.042 Uiso 1 1 calc R . .
C2 C 0.6397(7) -0.0498(5) 0.1958(2) 0.0253(11) Uani 1 1 d . . .
C3 C 0.6635(6) 0.0557(4) 0.1499(2) 0.0163(9) Uani 1 1 d . . .
C4 C 0.5440(6) 0.1478(6) 0.1239(3) 0.0295(12) Uani 1 1 d . . .
C5 C 0.8217(6) 0.0639(6) 0.1447(3) 0.0297(13) Uani 1 1 d . . .
H5 H 0.8683 0.1336 0.1211 0.036 Uiso 1 1 calc R . .
C6 C 0.8326(7) -0.2167(6) 0.2437(3) 0.0316(13) Uani 1 1 d . . .
H6A H 0.7453 -0.2415 0.2696 0.038 Uiso 1 1 calc R . .
H6B H 0.9194 -0.1901 0.2695 0.038 Uiso 1 1 calc R . .
C7 C 1.1720(7) -0.2835(6) 0.1997(3) 0.0328(13) Uani 1 1 d . . .
H7A H 1.1482 -0.2049 0.2256 0.049 Uiso 1 1 calc R . .
H7B H 1.2146 -0.2492 0.1622 0.049 Uiso 1 1 calc R . .
H7C H 1.2467 -0.3439 0.2192 0.049 Uiso 1 1 calc R . .
C8 C 1.0256(6) -0.3659(5) 0.1870(2) 0.0215(11) Uani 1 1 d . . .
C9 C 1.0021(5) -0.4860(5) 0.1451(2) 0.0164(10) Uani 1 1 d . . .
C10 C 1.1188(6) -0.5689(6) 0.1149(3) 0.0296(12) Uani 1 1 d . . .
C11 C 0.8339(6) -0.5037(6) 0.1465(2) 0.0253(11) Uani 1 1 d . . .
H11 H 0.7825 -0.5701 0.1226 0.030 Uiso 1 1 calc R . .
C12 C 0.5136(6) 0.5719(6) 0.0420(2) 0.0268(12) Uani 1 1 d . . .
H12 H 0.4964 0.5869 0.0832 0.032 Uiso 1 1 calc R . .
C13 C 0.6551(8) 0.6369(6) -0.0502(2) 0.0353(13) Uani 1 1 d . . .
H13A H 0.6655 0.5374 -0.0579 0.053 Uiso 1 1 calc R . .
H13B H 0.7532 0.6830 -0.0575 0.053 Uiso 1 1 calc R . .
H13C H 0.5774 0.6760 -0.0767 0.053 Uiso 1 1 calc R . .
C14 C 0.6696(7) 0.7868(7) 0.0432(3) 0.0362(14) Uani 1 1 d . . .
H14A H 0.6006 0.8113 0.0759 0.054 Uiso 1 1 calc R . .
H14B H 0.6753 0.8641 0.0150 0.054 Uiso 1 1 calc R . .
H14C H 0.7716 0.7677 0.0591 0.054 Uiso 1 1 calc R . .
N1 N 0.9035(7) -0.0271(6) 0.1731(2) 0.0402(13) Uani 1 1 d . . .
N2 N 0.7910(5) -0.1009(5) 0.2064(2) 0.0252(10) Uani 1 1 d . . .
N3 N 0.8767(5) -0.3402(4) 0.20671(19) 0.0237(9) Uani 1 1 d . . .
N4 N 0.7632(7) -0.4229(5) 0.1822(2) 0.0372(12) Uani 1 1 d . . .
N5 N 0.6095(6) 0.6585(5) 0.0116(2) 0.0311(11) Uani 1 1 d . . .
O1 O 0.5894(4) 0.2416(4) 0.08473(17) 0.0280(9) Uani 1 1 d . . .
O2 O 0.3942(4) 0.1349(4) 0.13588(17) 0.0316(9) Uani 1 1 d . . .
O3 O 1.0888(5) -0.6643(4) 0.07412(18) 0.0337(9) Uani 1 1 d . . .
O4 O 1.2612(4) -0.5524(4) 0.12729(19) 0.0308(9) Uani 1 1 d . . .
O5 O 0.4455(5) 0.4694(4) 0.01536(18) 0.0330(10) Uani 1 1 d . . .
O6 O 0.3210(4) 0.1950(4) -0.00560(16) 0.0272(8) Uani 1 1 d . . .
H6Y H 0.2181 0.1551 -0.0042 0.033 Uiso 1 1 d R . .
H6X H 0.3966 0.1203 -0.0074 0.033 Uiso 1 1 d R . .
Zn1 Zn 0.35681(8) 0.30841(7) 0.06704(3) 0.03309(19) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.467(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N2 1.404(8) . ?
C2 C3 1.433(7) . ?
C3 C5 1.364(7) . ?
C3 C4 1.462(7) . ?
C4 O1 1.297(7) . ?
C4 O2 1.317(7) . ?
C4 Zn1 2.540(6) . ?
C5 N1 1.274(7) . ?
C5 H5 0.9300 . ?
C6 N2 1.414(7) . ?
C6 N3 1.473(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.503(8) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N3 1.371(7) . ?
C8 C9 1.478(6) . ?
C9 C10 1.434(7) . ?
C9 C11 1.453(7) . ?
C10 O4 1.261(7) . ?
C10 O3 1.298(7) . ?
C10 Zn1 2.574(5) 1_645 ?
C11 N4 1.252(7) . ?
C11 H11 0.9300 . ?
C12 O5 1.274(7) . ?
C12 N5 1.340(7) . ?
C12 H12 0.9300 . ?
C13 N5 1.431(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N5 1.491(8) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 N2 1.399(7) . ?
N3 N4 1.361(7) . ?
O1 Zn1 2.128(4) . ?
O2 Zn1 2.257(4) . ?
O3 Zn1 2.318(4) 1_645 ?
O4 Zn1 2.041(4) 1_645 ?
O5 Zn1 2.047(4) . ?
O6 Zn1 1.950(4) . ?
O6 H6Y 0.9600 . ?
O6 H6X 0.9600 . ?
Zn1 O4 2.041(4) 1_465 ?
Zn1 O3 2.318(4) 1_465 ?
Zn1 C10 2.574(6) 1_465 ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 C3 103.1(4) . . ?
N2 C2 C1 121.5(5) . . ?
C3 C2 C1 135.4(5) . . ?
C5 C3 C2 103.9(5) . . ?
C5 C3 C4 129.1(4) . . ?
C2 C3 C4 126.2(5) . . ?
O1 C4 O2 119.3(5) . . ?
O1 C4 C3 117.2(5) . . ?
O2 C4 C3 123.4(5) . . ?
O1 C4 Zn1 56.8(3) . . ?
O2 C4 Zn1 62.5(3) . . ?
C3 C4 Zn1 173.0(4) . . ?
N1 C5 C3 117.9(5) . . ?
N1 C5 H5 121.1 . . ?
C3 C5 H5 121.1 . . ?
N2 C6 N3 110.9(4) . . ?
N2 C6 H6A 109.5 . . ?
N3 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
N3 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 101.9(4) . . ?
N3 C8 C7 128.9(4) . . ?
C9 C8 C7 128.9(5) . . ?
C10 C9 C11 129.8(5) . . ?
C10 C9 C8 127.9(4) . . ?
C11 C9 C8 102.1(4) . . ?
O4 C10 O3 115.3(5) . . ?
O4 C10 C9 120.5(5) . . ?
O3 C10 C9 124.2(5) . . ?
O4 C10 Zn1 51.4(3) . 1_645 ?
O3 C10 Zn1 64.0(3) . 1_645 ?
C9 C10 Zn1 171.7(4) . 1_645 ?
N4 C11 C9 115.1(5) . . ?
N4 C11 H11 122.4 . . ?
C9 C11 H11 122.4 . . ?
O5 C12 N5 121.0(5) . . ?
O5 C12 H12 119.5 . . ?
N5 C12 H12 119.5 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 N1 N2 102.4(5) . . ?
N1 N2 C2 112.2(4) . . ?
N1 N2 C6 121.1(5) . . ?
C2 N2 C6 126.7(4) . . ?
N4 N3 C8 116.1(4) . . ?
N4 N3 C6 119.4(4) . . ?
C8 N3 C6 123.7(4) . . ?
C11 N4 N3 104.6(5) . . ?
C12 N5 C13 123.9(5) . . ?
C12 N5 C14 118.3(5) . . ?
C13 N5 C14 117.8(4) . . ?
C4 O1 Zn1 92.5(3) . . ?
C4 O2 Zn1 86.4(3) . . ?
C10 O3 Zn1 85.8(3) . 1_645 ?
C10 O4 Zn1 99.7(4) . 1_645 ?
C12 O5 Zn1 118.6(3) . . ?
Zn1 O6 H6Y 109.5 . . ?
Zn1 O6 H6X 109.3 . . ?
H6Y O6 H6X 109.5 . . ?
O6 Zn1 O4 145.54(15) . 1_465 ?
O6 Zn1 O5 90.57(17) . . ?
O4 Zn1 O5 91.85(17) 1_465 . ?
O6 Zn1 O1 97.77(15) . . ?
O4 Zn1 O1 116.65(16) 1_465 . ?
O5 Zn1 O1 88.50(16) . . ?
O6 Zn1 O2 100.09(16) . . ?
O4 Zn1 O2 95.05(16) 1_465 . ?
O5 Zn1 O2 149.43(16) . . ?
O1 Zn1 O2 61.84(14) . . ?
O6 Zn1 O3 87.71(14) . 1_465 ?
O4 Zn1 O3 59.08(14) 1_465 1_465 ?
O5 Zn1 O3 108.87(16) . 1_465 ?
O1 Zn1 O3 161.80(15) . 1_465 ?
O2 Zn1 O3 100.17(15) . 1_465 ?
O6 Zn1 C4 100.17(18) . . ?
O4 Zn1 C4 108.53(19) 1_465 . ?
O5 Zn1 C4 118.92(17) . . ?
O1 Zn1 C4 30.68(16) . . ?
O2 Zn1 C4 31.16(16) . . ?
O3 Zn1 C4 131.29(16) 1_465 . ?
O6 Zn1 C10 117.30(16) . 1_465 ?
O4 Zn1 C10 28.89(17) 1_465 1_465 ?
O5 Zn1 C10 100.84(18) . 1_465 ?
O1 Zn1 C10 143.33(17) . 1_465 ?
O2 Zn1 C10 99.49(17) . 1_465 ?
O3 Zn1 C10 30.21(16) 1_465 1_465 ?
C4 Zn1 C10 124.64(19) . 1_465 ?

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
N2 C2 C3 C5 -6.4(5) . . . . ?
C1 C2 C3 C5 171.6(6) . . . . ?
N2 C2 C3 C4 -176.9(5) . . . . ?
C1 C2 C3 C4 1.0(9) . . . . ?
C5 C3 C4 O1 8.8(9) . . . . ?
C2 C3 C4 O1 176.9(5) . . . . ?
C5 C3 C4 O2 -174.9(6) . . . . ?
C2 C3 C4 O2 -6.8(9) . . . . ?
C2 C3 C5 N1 7.9(7) . . . . ?
C4 C3 C5 N1 178.0(6) . . . . ?
N3 C8 C9 C10 -173.2(5) . . . . ?
C7 C8 C9 C10 12.5(9) . . . . ?
N3 C8 C9 C11 2.6(5) . . . . ?
C7 C8 C9 C11 -171.6(5) . . . . ?
C11 C9 C10 O4 -167.5(6) . . . . ?
C8 C9 C10 O4 7.2(9) . . . . ?
C11 C9 C10 O3 12.2(10) . . . . ?
C10 C9 C11 N4 172.8(6) . . . . ?
C8 C9 C11 N4 -3.0(7) . . . . ?
C3 C5 N1 N2 -5.4(8) . . . . ?
C5 N1 N2 C2 0.5(7) . . . . ?
C5 N1 N2 C6 178.0(5) . . . . ?
C3 C2 N2 N1 3.8(6) . . . . ?
C1 C2 N2 N1 -174.4(5) . . . . ?
C3 C2 N2 C6 -173.4(5) . . . . ?
C1 C2 N2 C6 8.3(8) . . . . ?
N3 C6 N2 N1 -71.2(6) . . . . ?
N3 C6 N2 C2 105.8(6) . . . . ?
C9 C8 N3 N4 -1.9(6) . . . . ?
C7 C8 N3 N4 172.3(5) . . . . ?
C9 C8 N3 C6 -171.5(4) . . . . ?
C7 C8 N3 C6 2.8(8) . . . . ?
N2 C6 N3 N4 -79.9(6) . . . . ?
N2 C6 N3 C8 89.3(6) . . . . ?
C9 C11 N4 N3 1.8(7) . . . . ?
C8 N3 N4 C11 0.2(7) . . . . ?
C6 N3 N4 C11 170.2(5) . . . . ?
O5 C12 N5 C13 -6.1(9) . . . . ?
O5 C12 N5 C14 172.4(5) . . . . ?
O2 C4 O1 Zn1 -0.8(6) . . . . ?
C3 C4 O1 Zn1 175.6(4) . . . . ?
O1 C4 O2 Zn1 0.8(5) . . . . ?
C3 C4 O2 Zn1 -175.4(5) . . . . ?
O4 C10 O3 Zn1 -2.4(5) . . . 1_645 ?
C9 C10 O3 Zn1 177.9(5) . . . 1_645 ?
O3 C10 O4 Zn1 2.8(5) . . . 1_645 ?
C9 C10 O4 Zn1 -177.5(4) . . . 1_645 ?
N5 C12 O5 Zn1 161.5(4) . . . . ?
C12 O5 Zn1 O6 -169.4(4) . . . . ?
C12 O5 Zn1 O4 44.9(4) . . . 1_465 ?
C12 O5 Zn1 O1 -71.7(4) . . . . ?
C12 O5 Zn1 O2 -58.2(6) . . . . ?
C12 O5 Zn1 O3 102.8(4) . . . 1_465 ?
C12 O5 Zn1 C4 -67.5(5) . . . . ?
C12 O5 Zn1 C10 72.6(4) . . . 1_465 ?
C4 O1 Zn1 O6 -96.9(3) . . . . ?
C4 O1 Zn1 O4 81.4(4) . . . 1_465 ?
C4 O1 Zn1 O5 172.8(3) . . . . ?
C4 O1 Zn1 O2 0.5(3) . . . . ?
C4 O1 Zn1 O3 9.8(6) . . . 1_465 ?
C4 O1 Zn1 C10 66.5(4) . . . 1_465 ?
C4 O2 Zn1 O6 93.0(3) . . . . ?
C4 O2 Zn1 O4 -118.1(3) . . . 1_465 ?
C4 O2 Zn1 O5 -15.7(5) . . . . ?
C4 O2 Zn1 O1 -0.5(3) . . . . ?
C4 O2 Zn1 O3 -177.5(3) . . . 1_465 ?
C4 O2 Zn1 C10 -146.9(3) . . . 1_465 ?
O1 C4 Zn1 O6 88.1(3) . . . . ?
O2 C4 Zn1 O6 -92.7(3) . . . . ?
O1 C4 Zn1 O4 -111.2(3) . . . 1_465 ?
O2 C4 Zn1 O4 68.0(3) . . . 1_465 ?
O1 C4 Zn1 O5 -8.3(4) . . . . ?
O2 C4 Zn1 O5 170.9(3) . . . . ?
O2 C4 Zn1 O1 179.2(6) . . . . ?
O1 C4 Zn1 O2 -179.2(6) . . . . ?
O1 C4 Zn1 O3 -176.0(3) . . . 1_465 ?
O2 C4 Zn1 O3 3.2(4) . . . 1_465 ?
O1 C4 Zn1 C10 -138.3(3) . . . 1_465 ?
O2 C4 Zn1 C10 40.9(4) . . . 1_465 ?

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
O6 H6Y O5 0.96 2.63 3.582(6) 172 4_455
O6 H6X O3 0.96 2.25 2.765(5) 113 4_445

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1534604'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 N4 O4'
_chemical_formula_sum            'C11 H12 N4 O4'
_chemical_formula_weight         264.25

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           orthorhombic
_symmetry_space_group_name_H-M   'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'

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'

_cell_length_a                   23.952(7)
_cell_length_b                   4.0594(13)
_cell_length_c                   12.531(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1218.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1417
_cell_measurement_theta_min      3.252
_cell_measurement_theta_max      22.459

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.441
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_T_max  0.9801
_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6996
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         27.62
_reflns_number_total             1460
_reflns_number_gt                1058
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.1019P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'

_refine_ls_number_reflns         1460
_refine_ls_number_parameters     176
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1609
_refine_ls_wR_factor_gt          0.1437
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C1 C 0.29682(19) 0.3960(12) 0.1716(4) 0.0486(11) Uani 1 1 d . . .
H1A H 0.2763 0.2427 0.1285 0.073 Uiso 1 1 calc R . .
H1B H 0.3356 0.3890 0.1521 0.073 Uiso 1 1 calc R . .
H1C H 0.2826 0.6143 0.1603 0.073 Uiso 1 1 calc R . .
C2 C 0.29074(16) 0.3067(10) 0.2856(4) 0.0345(9) Uani 1 1 d . . .
C3 C 0.32473(16) 0.1355(10) 0.3547(4) 0.0356(9) Uani 1 1 d . . .
C4 C 0.37945(17) -0.0095(12) 0.3322(4) 0.0421(10) Uani 1 1 d . . .
C5 C 0.29694(18) 0.1265(11) 0.4537(4) 0.0424(10) Uani 1 1 d . . .
H5 H 0.3107 0.0238 0.5146 0.051 Uiso 1 1 calc R . .
C6 C 0.19727(19) 0.5799(9) 0.3150(4) 0.0394(9) Uani 1 1 d . . .
H6A H 0.2074 0.7265 0.2570 0.047 Uiso 1 1 calc R . .
H6B H 0.1854 0.7144 0.3749 0.047 Uiso 1 1 calc R . .
C7 C 0.0969(2) 0.3536(12) 0.4535(4) 0.0502(12) Uani 1 1 d . . .
H7A H 0.1313 0.3241 0.4915 0.075 Uiso 1 1 calc R . .
H7B H 0.0690 0.2093 0.4826 0.075 Uiso 1 1 calc R . .
H7C H 0.0847 0.5779 0.4606 0.075 Uiso 1 1 calc R . .
C8 C 0.10554(16) 0.2751(10) 0.3382(4) 0.0369(10) Uani 1 1 d . . .
C9 C 0.07325(18) 0.0962(10) 0.2660(4) 0.0398(10) Uani 1 1 d . . .
C10 C 0.01960(19) -0.0572(10) 0.2848(4) 0.0430(10) Uani 1 1 d . . .
C11 C 0.10309(18) 0.1022(11) 0.1695(4) 0.0441(11) Uani 1 1 d . . .
H11 H 0.0911 0.0011 0.1070 0.053 Uiso 1 1 calc R . .
N1 N 0.24858(16) 0.2834(9) 0.4486(3) 0.0426(9) Uani 1 1 d . . .
N2 N 0.24560(14) 0.3900(8) 0.3458(3) 0.0357(8) Uani 1 1 d . . .
N3 N 0.15099(14) 0.3731(8) 0.2813(3) 0.0368(8) Uani 1 1 d . . .
N4 N 0.15023(15) 0.2683(10) 0.1782(3) 0.0453(9) Uani 1 1 d . . .
O1 O 0.40046(14) -0.0097(11) 0.2422(3) 0.0578(10) Uani 1 1 d . . .
O2 O 0.40390(16) -0.1371(11) 0.4150(3) 0.0649(12) Uani 1 1 d . . .
H2 H 0.4355 -0.1957 0.3987 0.097 Uiso 1 1 calc R . .
O3 O -0.00279(14) -0.1907(10) 0.2012(3) 0.0612(10) Uani 1 1 d . . .
H3 H -0.0279 -0.3157 0.2197 0.092 Uiso 1 1 calc R . .
O4 O -0.00225(15) -0.0621(11) 0.3747(3) 0.0658(11) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.481(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N2 1.362(6) . ?
C2 C3 1.377(6) . ?
C3 C5 1.408(7) . ?
C3 C4 1.464(6) . ?
C4 O1 1.235(6) . ?
C4 O2 1.300(6) . ?
C5 N1 1.324(6) . ?
C5 H5 0.9300 . ?
C6 N2 1.443(6) . ?
C6 N3 1.453(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.494(7) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N3 1.361(6) . ?
C8 C9 1.395(6) . ?
C9 C11 1.404(7) . ?
C9 C10 1.448(6) . ?
C10 O4 1.241(7) . ?
C10 O3 1.296(7) . ?
C11 N4 1.320(6) . ?
C11 H11 0.9300 . ?
N1 N2 1.360(6) . ?
N3 N4 1.360(6) . ?
O2 H2 0.8200 . ?
O3 H3 0.8200 . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 C3 104.2(4) . . ?
N2 C2 C1 123.5(4) . . ?
C3 C2 C1 132.3(4) . . ?
C2 C3 C5 106.7(4) . . ?
C2 C3 C4 127.6(4) . . ?
C5 C3 C4 125.6(4) . . ?
O1 C4 O2 123.1(4) . . ?
O1 C4 C3 122.8(4) . . ?
O2 C4 C3 114.2(4) . . ?
N1 C5 C3 111.0(4) . . ?
N1 C5 H5 124.5 . . ?
C3 C5 H5 124.5 . . ?
N2 C6 N3 112.4(3) . . ?
N2 C6 H6A 109.1 . . ?
N3 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
N3 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 104.8(4) . . ?
N3 C8 C7 123.8(4) . . ?
C9 C8 C7 131.5(4) . . ?
C8 C9 C11 105.5(4) . . ?
C8 C9 C10 127.6(5) . . ?
C11 C9 C10 126.9(4) . . ?
O4 C10 O3 123.5(4) . . ?
O4 C10 C9 122.0(4) . . ?
O3 C10 C9 114.5(4) . . ?
N4 C11 C9 111.9(4) . . ?
N4 C11 H11 124.0 . . ?
C9 C11 H11 124.0 . . ?
C5 N1 N2 104.2(4) . . ?
N1 N2 C2 113.9(3) . . ?
N1 N2 C6 117.7(4) . . ?
C2 N2 C6 128.4(4) . . ?
N4 N3 C8 113.3(4) . . ?
N4 N3 C6 117.8(4) . . ?
C8 N3 C6 128.8(5) . . ?
C11 N4 N3 104.4(4) . . ?
C4 O2 H2 109.5 . . ?
C10 O3 H3 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_mo_121025a_0m
_database_code_depnum_ccdc_archive 'CCDC 1534606'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H19 N5 O6 Zn'
_chemical_formula_sum            'C14 H19 N5 O6 Zn'
_chemical_formula_weight         418.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   8.5459(4)
_cell_length_b                   9.4075(5)
_cell_length_c                   21.8986(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1760.55(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3698
_cell_measurement_theta_min      2.558
_cell_measurement_theta_max      24.078

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    1.437
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7063
_exptl_absorpt_correction_T_max  0.7620
_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9704
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0438
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3064
_reflns_number_gt                2847
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.0252P)²+0.2229P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.024(11)
_refine_ls_number_reflns         3064
_refine_ls_number_parameters     233
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0662
_refine_ls_wR_factor_gt          0.0651
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.061
_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
C1 C 0.0039(4) 1.1009(4) 0.22767(17) 0.0490(9) Uani 1 1 d . . .
H1A H -0.0010 1.0631 0.2683 0.074 Uiso 1 1 calc R . .
H1B H -0.0879 1.0730 0.2054 0.074 Uiso 1 1 calc R . .
H1C H 0.0092 1.2028 0.2295 0.074 Uiso 1 1 calc R . .
C2 C 0.1446(3) 1.0455(3) 0.19644(12) 0.0281(6) Uani 1 1 d . . .
C3 C 0.1643(3) 0.9379(3) 0.15356(12) 0.0290(6) Uani 1 1 d . . .
C4 C 0.0433(3) 0.8481(3) 0.12497(12) 0.0314(7) Uani 1 1 d U . .
C5 C 0.3249(3) 0.9347(3) 0.14191(14) 0.0366(7) Uani 1 1 d . . .
H5 H 0.3714 0.8722 0.1145 0.044 Uiso 1 1 calc R . .
C6 C 0.3354(3) 1.2179(3) 0.24379(12) 0.0299(7) Uani 1 1 d . . .
H6A H 0.2489 1.2457 0.2698 0.036 Uiso 1 1 calc R . .
H6B H 0.4229 1.1923 0.2698 0.036 Uiso 1 1 calc R . .
C7 C 0.6663(3) 1.2928(3) 0.20328(13) 0.0362(7) Uani 1 1 d . . .
H7A H 0.6812 1.3007 0.2466 0.054 Uiso 1 1 calc R . .
H7B H 0.7550 1.3325 0.1825 0.054 Uiso 1 1 calc R . .
H7C H 0.6554 1.1945 0.1924 0.054 Uiso 1 1 calc R . .
C8 C 0.5218(3) 1.3718(3) 0.18521(12) 0.0252(6) Uani 1 1 d . . .
C9 C 0.5006(3) 1.4867(3) 0.14637(12) 0.0263(6) Uani 1 1 d . . .
C10 C 0.6206(3) 1.5677(3) 0.11370(12) 0.0312(6) Uani 1 1 d . . .
C11 C 0.3383(3) 1.5100(3) 0.14667(13) 0.0338(7) Uani 1 1 d . . .
H11 H 0.2894 1.5816 0.1244 0.041 Uiso 1 1 calc R . .
C12 C 0.0180(4) 0.4257(4) 0.04087(16) 0.0481(8) Uani 1 1 d U . .
H12 H -0.0031 0.4101 0.0820 0.058 Uiso 1 1 calc R . .
C13 C 0.1638(7) 0.3604(6) -0.04867(18) 0.0941(12) Uani 1 1 d U . .
H13A H 0.1030 0.4362 -0.0660 0.141 Uiso 1 1 calc R . .
H13B H 0.1473 0.2751 -0.0718 0.141 Uiso 1 1 calc R . .
H13C H 0.2727 0.3854 -0.0497 0.141 Uiso 1 1 calc R . .
C14 C 0.1845(6) 0.2197(6) 0.04608(19) 0.0941(12) Uani 1 1 d U . .
H14A H 0.1594 0.2284 0.0886 0.141 Uiso 1 1 calc R . .
H14B H 0.2961 0.2205 0.0410 0.141 Uiso 1 1 calc R . .
H14C H 0.1429 0.1321 0.0306 0.141 Uiso 1 1 calc R . .
N1 N 0.4036(3) 1.0296(3) 0.17378(11) 0.0387(6) Uani 1 1 d . . .
N2 N 0.2902(3) 1.0965(3) 0.20739(11) 0.0285(5) Uani 1 1 d . . .
N3 N 0.3792(2) 1.3357(2) 0.20525(9) 0.0264(5) Uani 1 1 d . . .
N4 N 0.2632(3) 1.4198(3) 0.18179(11) 0.0361(6) Uani 1 1 d . . .
N5 N 0.1168(4) 0.3376(3) 0.01292(12) 0.0571(8) Uani 1 1 d U . .
O1 O 0.0872(2) 0.7552(2) 0.08656(9) 0.0359(5) Uani 1 1 d U . .
O2 O -0.0986(2) 0.8611(2) 0.13696(10) 0.0440(6) Uani 1 1 d . . .
O4 O 0.7628(2) 1.5507(2) 0.12758(10) 0.0419(5) Uani 1 1 d . . .
O3 O 0.5832(2) 1.6555(2) 0.07303(10) 0.0497(6) Uani 1 1 d . . .
O6 O -0.1785(2) 0.8109(2) -0.00604(8) 0.0390(5) Uani 1 1 d . . .
H6X H -0.0980 0.8219 -0.0314 0.059 Uiso 1 1 d R . .
H6Y H -0.2560 0.7657 -0.0293 0.059 Uiso 1 1 d R . .
O5 O -0.0461(3) 0.5246(3) 0.01606(10) 0.0495(6) Uani 1 1 d . . .
Zn1 Zn -0.14065(4) 0.68915(4) 0.067074(14) 0.03207(10) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.478(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N2 1.355(4) . ?
C2 C3 1.391(4) . ?
C3 C5 1.396(4) . ?
C3 C4 1.475(4) . ?
C4 O2 1.247(3) . ?
C4 O1 1.270(4) . ?
C5 N1 1.318(4) . ?
C5 H5 0.9300 . ?
C6 N3 1.443(3) . ?
C6 N2 1.445(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.494(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 N3 1.339(3) . ?
C8 C9 1.387(4) . ?
C9 C11 1.404(4) . ?
C9 C10 1.464(4) . ?
C10 O3 1.256(3) . ?
C10 O4 1.263(4) . ?
C10 Zn1 2.552(3) 1_665 ?
C11 N4 1.313(4) . ?
C11 H11 0.9300 . ?
C12 O5 1.208(4) . ?
C12 N5 1.332(4) . ?
C12 H12 0.9300 . ?
C13 N5 1.423(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N5 1.446(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 N2 1.370(3) . ?
N3 N4 1.369(3) . ?
O1 Zn1 2.0882(19) . ?
O2 Zn1 2.255(2) . ?
O4 Zn1 2.033(2) 1_665 ?
O3 Zn1 2.385(2) 1_665 ?
O6 Zn1 1.995(2) . ?
O6 H6X 0.8898 . ?
O6 H6Y 0.9369 . ?
O5 Zn1 2.073(2) . ?
Zn1 O4 2.033(2) 1_445 ?
Zn1 O3 2.385(2) 1_445 ?
Zn1 C10 2.552(3) 1_445 ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 C3 105.4(2) . . ?
N2 C2 C1 122.7(3) . . ?
C3 C2 C1 131.9(3) . . ?
C2 C3 C5 104.9(3) . . ?
C2 C3 C4 128.2(3) . . ?
C5 C3 C4 126.8(3) . . ?
O2 C4 O1 119.6(3) . . ?
O2 C4 C3 122.5(3) . . ?
O1 C4 C3 117.9(3) . . ?
N1 C5 C3 113.0(3) . . ?
N1 C5 H5 123.5 . . ?
C3 C5 H5 123.5 . . ?
N3 C6 N2 110.7(2) . . ?
N3 C6 H6A 109.5 . . ?
N2 C6 H6A 109.5 . . ?
N3 C6 H6B 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 108.1 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 C9 106.2(2) . . ?
N3 C8 C7 122.6(3) . . ?
C9 C8 C7 131.2(3) . . ?
C8 C9 C11 104.4(2) . . ?
C8 C9 C10 127.8(3) . . ?
C11 C9 C10 127.8(3) . . ?
O3 C10 O4 119.9(3) . . ?
O3 C10 C9 120.7(3) . . ?
O4 C10 C9 119.4(3) . . ?
O3 C10 Zn1 68.01(15) . 1_665 ?
O4 C10 Zn1 51.95(14) . 1_665 ?
C9 C10 Zn1 171.3(2) . 1_665 ?
N4 C11 C9 112.6(3) . . ?
N4 C11 H11 123.7 . . ?
C9 C11 H11 123.7 . . ?
O5 C12 N5 124.0(3) . . ?
O5 C12 H12 118.0 . . ?
N5 C12 H12 118.0 . . ?
N5 C13 H13A 109.5 . . ?
N5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N5 C14 H14A 109.5 . . ?
N5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 N1 N2 103.6(2) . . ?
C2 N2 N1 113.1(2) . . ?
C2 N2 C6 128.5(2) . . ?
N1 N2 C6 118.1(2) . . ?
C8 N3 N4 113.0(2) . . ?
C8 N3 C6 128.5(2) . . ?
N4 N3 C6 118.4(2) . . ?
C11 N4 N3 103.8(2) . . ?
C12 N5 C13 121.3(3) . . ?
C12 N5 C14 120.0(3) . . ?
C13 N5 C14 118.6(3) . . ?
C4 O1 Zn1 93.69(17) . . ?
C4 O2 Zn1 86.66(17) . . ?
C10 O4 Zn1 98.78(18) . 1_665 ?
C10 O3 Zn1 82.76(17) . 1_665 ?
Zn1 O6 H6X 116.2 . . ?
Zn1 O6 H6Y 106.8 . . ?
H6X O6 H6Y 105.1 . . ?
C12 O5 Zn1 120.6(2) . . ?
O6 Zn1 O4 145.58(8) . 1_445 ?
O6 Zn1 O5 93.41(9) . . ?
O4 Zn1 O5 91.78(10) 1_445 . ?
O6 Zn1 O1 98.31(8) . . ?
O4 Zn1 O1 115.86(8) 1_445 . ?
O5 Zn1 O1 88.21(9) . . ?
O6 Zn1 O2 99.13(9) . . ?
O4 Zn1 O2 94.69(9) 1_445 . ?
O5 Zn1 O2 147.05(9) . . ?
O1 Zn1 O2 59.97(7) . . ?
O6 Zn1 O3 87.68(7) . 1_445 ?
O4 Zn1 O3 58.50(8) 1_445 1_445 ?
O5 Zn1 O3 108.43(9) . 1_445 ?
O1 Zn1 O3 162.04(8) . 1_445 ?
O2 Zn1 O3 102.45(8) . 1_445 ?
O6 Zn1 C10 116.64(9) . 1_445 ?
O4 Zn1 C10 29.27(9) 1_445 1_445 ?
O5 Zn1 C10 101.13(9) . 1_445 ?
O1 Zn1 C10 142.86(8) . 1_445 ?
O2 Zn1 C10 100.19(8) . 1_445 ?
O3 Zn1 C10 29.23(8) 1_445 1_445 ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 796444'
_audit_update_record             
;
2017-02-24 deposited with the CCDC.
2017-05-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H20 N4 O4'
_chemical_formula_sum            'C15 H20 N4 O4'
_chemical_formula_weight         320.35

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   12.259(4)
_cell_length_b                   8.409(3)
_cell_length_c                   32.758(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3376.8(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2960
_cell_measurement_theta_min      2.08
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9771
_exptl_absorpt_correction_T_max  0.9834
_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 ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17055
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_sigmaI/netI    0.0538
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2960
_reflns_number_gt                1956
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX II'
_computing_cell_refinement       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_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)+(0.1259P)²+0.2369P] 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         2960
_refine_ls_number_parameters     224
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.2112
_refine_ls_wR_factor_gt          0.1910
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_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 0.9063(3) 0.7658(4) 0.55470(9) 0.1299(12) Uani 1 1 d . . .
O2 O 0.7318(2) 0.8159(3) 0.56827(8) 0.0991(9) Uani 1 1 d . . .
O3 O 1.03286(16) 1.0599(3) 0.83713(6) 0.0770(7) Uani 1 1 d . . .
O4 O 0.88213(15) 0.9491(3) 0.86272(6) 0.0697(6) Uani 1 1 d . . .
N1 N 0.84183(17) 1.0831(3) 0.66401(6) 0.0538(6) Uani 1 1 d . . .
N2 N 0.95183(18) 1.0624(3) 0.65991(7) 0.0662(7) Uani 1 1 d . . .
N3 N 0.81577(15) 1.1141(2) 0.73638(6) 0.0455(5) Uani 1 1 d . . .
N4 N 0.73939(16) 1.0075(3) 0.74972(7) 0.0569(6) Uani 1 1 d . . .
C1 C 0.9619(3) 0.9664(4) 0.62816(10) 0.0687(9) Uani 1 1 d . A .
C2 C 0.8599(2) 0.9248(4) 0.61180(8) 0.0597(8) Uani 1 1 d . . .
C3 C 0.7857(2) 1.0033(3) 0.63593(8) 0.0534(7) Uani 1 1 d . A .
H3A H 0.7102 1.0010 0.6332 0.064 Uiso 1 1 calc R . .
C4 C 1.0736(3) 0.9176(6) 0.61376(13) 0.1078(14) Uani 1 1 d . . .
H4B H 1.1279 0.9644 0.6311 0.162 Uiso 1 1 calc R A .
H4C H 1.0844 0.9535 0.5862 0.162 Uiso 1 1 calc R . .
H4D H 1.0799 0.8039 0.6147 0.162 Uiso 1 1 calc R . .
C5 C 0.8379(4) 0.8283(4) 0.57596(10) 0.0811(10) Uani 1 1 d . A .
C6 C 0.6810(13) 0.7205(8) 0.5346(2) 0.100(3) Uani 0.64(2) 1 d P A 1
H6A H 0.7334 0.6445 0.5240 0.120 Uiso 0.64(2) 1 calc PR A 1
H6B H 0.6185 0.6623 0.5449 0.120 Uiso 0.64(2) 1 calc PR A 1
C7 C 0.6484(11) 0.8238(15) 0.5036(3) 0.125(4) Uani 0.64(2) 1 d PU A 1
H7A H 0.6098 0.9121 0.5153 0.188 Uiso 0.64(2) 1 calc PR A 1
H7B H 0.6015 0.7685 0.4850 0.188 Uiso 0.64(2) 1 calc PR A 1
H7C H 0.7115 0.8621 0.4893 0.188 Uiso 0.64(2) 1 calc PR A 1
C6A C 0.7329(13) 0.749(2) 0.5265(6) 0.093(5) Uiso 0.36(2) 1 d P A 2
H6A1 H 0.7720 0.6490 0.5252 0.111 Uiso 0.36(2) 1 calc PR A 2
H6A2 H 0.7632 0.8230 0.5068 0.111 Uiso 0.36(2) 1 calc PR A 2
C7A C 0.6065(13) 0.726(3) 0.5208(5) 0.099(6) Uani 0.36(2) 1 d PU A 2
H7A1 H 0.5770 0.6731 0.5442 0.148 Uiso 0.36(2) 1 calc PR A 2
H7A2 H 0.5931 0.6638 0.4968 0.148 Uiso 0.36(2) 1 calc PR A 2
H7A3 H 0.5724 0.8285 0.5179 0.148 Uiso 0.36(2) 1 calc PR A 2
C8 C 0.8012(2) 1.1841(3) 0.69642(8) 0.0538(7) Uani 1 1 d . . .
H8A H 0.8390 1.2854 0.6955 0.065 Uiso 1 1 calc R . .
H8B H 0.7242 1.2043 0.6920 0.065 Uiso 1 1 calc R . .
C9 C 0.7750(2) 0.9667(3) 0.78621(8) 0.0552(7) Uani 1 1 d . . .
H9A H 0.7390 0.8952 0.8032 0.066 Uiso 1 1 calc R . .
C10 C 0.87282(18) 1.0426(3) 0.79671(7) 0.0438(6) Uani 1 1 d . . .
C11 C 0.89748(17) 1.1369(3) 0.76350(7) 0.0435(6) Uani 1 1 d . . .
C12 C 0.9896(2) 1.2471(4) 0.75570(9) 0.0642(8) Uani 1 1 d . . .
H12A H 0.9815 1.2940 0.7291 0.096 Uiso 1 1 calc R . .
H12B H 1.0571 1.1894 0.7569 0.096 Uiso 1 1 calc R . .
H12C H 0.9899 1.3294 0.7760 0.096 Uiso 1 1 calc R . .
C13 C 0.9385(2) 1.0206(3) 0.83343(8) 0.0518(7) Uani 1 1 d . . .
C14 C 0.9395(3) 0.9103(5) 0.90017(9) 0.0841(11) Uani 1 1 d . . .
H14A H 0.9756 1.0040 0.9110 0.101 Uiso 1 1 calc R . .
H14B H 0.9942 0.8294 0.8950 0.101 Uiso 1 1 calc R . .
C15 C 0.8583(4) 0.8515(8) 0.92924(13) 0.139(2) Uani 1 1 d . . .
H15A H 0.8936 0.8243 0.9545 0.209 Uiso 1 1 calc R . .
H15B H 0.8232 0.7590 0.9182 0.209 Uiso 1 1 calc R . .
H15C H 0.8048 0.9328 0.9341 0.209 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 C5 1.210(4) . ?
O2 C5 1.330(4) . ?
O2 C6A 1.479(17) . ?
O2 C6 1.500(8) . ?
O3 C13 1.210(3) . ?
O4 C13 1.326(3) . ?
O4 C14 1.451(3) . ?
N1 C3 1.331(3) . ?
N1 N2 1.366(3) . ?
N1 C8 1.448(3) . ?
N2 C1 1.322(4) . ?
N3 C11 1.352(3) . ?
N3 N4 1.368(3) . ?
N3 C8 1.446(3) . ?
N4 C9 1.318(3) . ?
C1 C2 1.405(4) . ?
C1 C4 1.506(4) . ?
C2 C3 1.374(4) . ?
C2 C5 1.452(5) . ?
C3 H3A 0.9300 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C4 H4D 0.9600 . ?
C6 C7 1.393(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6A C7A 1.57(3) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C7A H7A1 0.9600 . ?
C7A H7A2 0.9600 . ?
C7A H7A3 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.402(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.380(3) . ?
C10 C13 1.459(4) . ?
C11 C12 1.483(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C15 1.464(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
C5 O2 C6A 101.3(6) . . ?
C5 O2 C6 125.9(6) . . ?
C6A O2 C6 28.3(5) . . ?
C13 O4 C14 117.5(2) . . ?
C3 N1 N2 112.2(2) . . ?
C3 N1 C8 128.7(2) . . ?
N2 N1 C8 119.1(2) . . ?
C1 N2 N1 104.3(2) . . ?
C11 N3 N4 113.0(2) . . ?
C11 N3 C8 128.9(2) . . ?
N4 N3 C8 118.1(2) . . ?
C9 N4 N3 103.53(19) . . ?
N2 C1 C2 111.7(3) . . ?
N2 C1 C4 119.8(3) . . ?
C2 C1 C4 128.5(3) . . ?
C3 C2 C1 104.5(3) . . ?
C3 C2 C5 127.6(3) . . ?
C1 C2 C5 127.8(3) . . ?
N1 C3 C2 107.3(3) . . ?
N1 C3 H3A 126.3 . . ?
C2 C3 H3A 126.3 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C1 C4 H4D 109.5 . . ?
H4B C4 H4D 109.5 . . ?
H4C C4 H4D 109.5 . . ?
O1 C5 O2 122.3(4) . . ?
O1 C5 C2 125.4(4) . . ?
O2 C5 C2 112.2(3) . . ?
C7 C6 O2 108.7(7) . . ?
C7 C6 H6A 109.9 . . ?
O2 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
O2 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
O2 C6A C7A 98.5(11) . . ?
O2 C6A H6A1 112.1 . . ?
C7A C6A H6A1 112.1 . . ?
O2 C6A H6A2 112.1 . . ?
C7A C6A H6A2 112.1 . . ?
H6A1 C6A H6A2 109.7 . . ?
C6A C7A H7A1 109.5 . . ?
C6A C7A H7A2 109.5 . . ?
H7A1 C7A H7A2 109.5 . . ?
C6A C7A H7A3 109.5 . . ?
H7A1 C7A H7A3 109.5 . . ?
H7A2 C7A H7A3 109.5 . . ?
N3 C8 N1 112.5(2) . . ?
N3 C8 H8A 109.1 . . ?
N1 C8 H8A 109.1 . . ?
N3 C8 H8B 109.1 . . ?
N1 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
N4 C9 C10 112.8(2) . . ?
N4 C9 H9A 123.6 . . ?
C10 C9 H9A 123.6 . . ?
C11 C10 C9 104.8(2) . . ?
C11 C10 C13 127.0(2) . . ?
C9 C10 C13 128.0(2) . . ?
N3 C11 C10 105.9(2) . . ?
N3 C11 C12 122.6(2) . . ?
C10 C11 C12 131.4(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O4 123.3(2) . . ?
O3 C13 C10 125.1(2) . . ?
O4 C13 C10 111.5(2) . . ?
O4 C14 C15 107.2(3) . . ?
O4 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O4 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
C3 H3A O3 0.93 2.43 3.257(4) 147.8 6_557

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.051
