# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_compound1
_database_code_depnum_ccdc_archive 'CCDC 1481592'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 N4 O2 Zn'
_chemical_formula_weight         303.60

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P c'

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

_cell_length_a                   4.8185(4)
_cell_length_b                   10.7128(9)
_cell_length_c                   10.5491(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.394(2)
_cell_angle_gamma                90.00
_cell_volume                     540.01(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1063
_cell_measurement_theta_min      0.761
_cell_measurement_theta_max      0.796

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    2.276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'Oxford Gemini S Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3901
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.80
_diffrn_reflns_theta_max         26.00
_reflns_number_total             1791
_reflns_number_gt                1754
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0182P)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_abs_structure_Flack   0.023(9)
_refine_ls_number_reflns         1791
_refine_ls_number_parameters     172
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0181
_refine_ls_R_factor_gt           0.0175
_refine_ls_wR_factor_ref         0.0422
_refine_ls_wR_factor_gt          0.0419
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
Zn1 Zn -0.77395(4) -0.642577(18) -0.20228(3) 0.01968(7) Uani 1 1 d . . .
N4 N -0.7154(5) -1.46281(18) -0.54702(19) 0.0224(4) Uani 1 1 d . . .
N1 N -0.7344(5) -1.56274(19) -0.36967(18) 0.0227(5) Uani 1 1 d . . .
O2 O -1.5530(3) -0.79564(15) -0.19100(14) 0.0251(3) Uani 1 1 d . . .
C7 C -0.9276(5) -1.3451(2) -0.3810(3) 0.0218(5) Uani 1 1 d . . .
N2 N -0.6082(5) -1.63651(17) -0.4514(2) 0.0306(5) Uani 1 1 d . . .
N3 N -0.5964(5) -1.57596(19) -0.55652(18) 0.0304(5) Uani 1 1 d . . .
O1 O -1.1720(4) -0.68987(15) -0.21600(16) 0.0262(4) Uani 1 1 d . . .
C6 C -1.1172(5) -1.3553(2) -0.2893(2) 0.0249(5) Uani 1 1 d . . .
H6A H -1.1664 -1.4337 -0.2615 0.030 Uiso 1 1 calc R . .
C12 C -0.7988(5) -1.4564(2) -0.4318(2) 0.0203(5) Uani 1 1 d . . .
C5 C -1.2269(5) -1.2514(2) -0.2418(2) 0.0280(5) Uani 1 1 d . . .
H5A H -1.3491 -1.2597 -0.1809 0.034 Uiso 1 1 calc R . .
C8 C -0.8609(5) -1.2295(2) -0.42375(19) 0.0220(5) Uani 1 1 d . . .
H8A H -0.7369 -1.2230 -0.4841 0.026 Uiso 1 1 calc R . .
C4 C -1.1593(5) -1.1303(2) -0.2831(2) 0.0220(5) Uani 1 1 d . . .
C10 C -0.9125(5) -1.0000(2) -0.4239(2) 0.0252(5) Uani 1 1 d . . .
H10A H -0.7973 -0.9925 -0.4878 0.030 Uiso 1 1 calc R . .
C9 C -0.9766(5) -1.1205(2) -0.3779(2) 0.0220(5) Uani 1 1 d . . .
C1 C -1.3120(5) -0.78959(19) -0.2241(2) 0.0191(5) Uani 1 1 d . . .
C2 C -1.1967(5) -0.9049(2) -0.2786(2) 0.0220(5) Uani 1 1 d . . .
C11 C -1.0199(5) -0.8956(2) -0.3742(2) 0.0251(5) Uani 1 1 d . . .
H11A H -0.9755 -0.8174 -0.4040 0.030 Uiso 1 1 calc R . .
C3 C -1.2706(5) -1.0203(2) -0.2352(2) 0.0238(5) Uani 1 1 d . . .
H3A H -1.3938 -1.0257 -0.1744 0.029 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
Zn1 O2 1.9504(16) 1_655 ?
Zn1 O1 1.9710(18) . ?
Zn1 N4 1.979(2) 2_535 ?
Zn1 N1 1.993(2) 1_565 ?
N4 C12 1.330(3) . ?
N4 N3 1.350(3) . ?
N4 Zn1 1.979(2) 2_534 ?
N1 C12 1.331(3) . ?
N1 N2 1.368(3) . ?
N1 Zn1 1.993(2) 1_545 ?
O2 C1 1.256(3) . ?
O2 Zn1 1.9504(16) 1_455 ?
C7 C8 1.370(3) . ?
C7 C6 1.418(4) . ?
C7 C12 1.477(3) . ?
N2 N3 1.293(3) . ?
O1 C1 1.261(3) . ?
C6 C5 1.355(3) . ?
C6 H6A 0.9300 . ?
C5 C4 1.421(3) . ?
C5 H5A 0.9300 . ?
C8 C9 1.406(3) . ?
C8 H8A 0.9300 . ?
C4 C3 1.414(3) . ?
C4 C9 1.419(3) . ?
C10 C11 1.364(3) . ?
C10 C9 1.427(3) . ?
C10 H10A 0.9300 . ?
C1 C2 1.499(3) . ?
C2 C3 1.381(3) . ?
C2 C11 1.405(3) . ?
C11 H11A 0.9300 . ?
C3 H3A 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
O2 Zn1 O1 107.87(7) 1_655 . ?
O2 Zn1 N4 114.24(8) 1_655 2_535 ?
O1 Zn1 N4 103.94(8) . 2_535 ?
O2 Zn1 N1 107.53(8) 1_655 1_565 ?
O1 Zn1 N1 104.38(8) . 1_565 ?
N4 Zn1 N1 117.95(8) 2_535 1_565 ?
C12 N4 N3 107.16(19) . . ?
C12 N4 Zn1 134.38(16) . 2_534 ?
N3 N4 Zn1 117.85(14) . 2_534 ?
C12 N1 N2 106.16(19) . . ?
C12 N1 Zn1 139.55(17) . 1_545 ?
N2 N1 Zn1 114.27(15) . 1_545 ?
C1 O2 Zn1 117.16(14) . 1_455 ?
C8 C7 C6 119.6(2) . . ?
C8 C7 C12 118.9(2) . . ?
C6 C7 C12 121.5(2) . . ?
N3 N2 N1 108.83(18) . . ?
N2 N3 N4 108.71(19) . . ?
C1 O1 Zn1 136.90(16) . . ?
C5 C6 C7 120.3(2) . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 H6A 119.8 . . ?
N4 C12 N1 109.13(19) . . ?
N4 C12 C7 124.3(2) . . ?
N1 C12 C7 126.5(2) . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C7 C8 C9 121.2(2) . . ?
C7 C8 H8A 119.4 . . ?
C9 C8 H8A 119.4 . . ?
C3 C4 C9 119.2(2) . . ?
C3 C4 C5 122.6(2) . . ?
C9 C4 C5 118.1(2) . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C8 C9 C4 119.4(2) . . ?
C8 C9 C10 121.5(2) . . ?
C4 C9 C10 119.2(2) . . ?
O1 C1 O2 122.0(2) . . ?
O1 C1 C2 120.2(2) . . ?
O2 C1 C2 117.7(2) . . ?
C3 C2 C11 120.5(2) . . ?
C3 C2 C1 119.1(2) . . ?
C11 C2 C1 120.4(2) . . ?
C10 C11 C2 120.9(2) . . ?
C10 C11 H11A 119.6 . . ?
C2 C11 H11A 119.6 . . ?
C2 C3 C4 120.1(2) . . ?
C2 C3 H3A 120.0 . . ?
C4 C3 H3A 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 N2 N3 0.5(3) . . . . ?
Zn1 N1 N2 N3 179.38(17) 1_545 . . . ?
N1 N2 N3 N4 -0.5(3) . . . . ?
C12 N4 N3 N2 0.3(3) . . . . ?
Zn1 N4 N3 N2 -171.97(18) 2_534 . . . ?
O2 Zn1 O1 C1 -3.5(2) 1_655 . . . ?
N4 Zn1 O1 C1 -125.1(2) 2_535 . . . ?
N1 Zn1 O1 C1 110.7(2) 1_565 . . . ?
C8 C7 C6 C5 -1.5(4) . . . . ?
C12 C7 C6 C5 178.3(2) . . . . ?
N3 N4 C12 N1 0.0(3) . . . . ?
Zn1 N4 C12 N1 170.48(18) 2_534 . . . ?
N3 N4 C12 C7 176.9(2) . . . . ?
Zn1 N4 C12 C7 -12.6(4) 2_534 . . . ?
N2 N1 C12 N4 -0.3(3) . . . . ?
Zn1 N1 C12 N4 -178.7(2) 1_545 . . . ?
N2 N1 C12 C7 -177.2(2) . . . . ?
Zn1 N1 C12 C7 4.5(4) 1_545 . . . ?
C8 C7 C12 N4 -28.1(4) . . . . ?
C6 C7 C12 N4 152.0(2) . . . . ?
C8 C7 C12 N1 148.2(2) . . . . ?
C6 C7 C12 N1 -31.6(4) . . . . ?
C7 C6 C5 C4 0.8(4) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C12 C7 C8 C9 -179.6(2) . . . . ?
C6 C5 C4 C3 180.0(2) . . . . ?
C6 C5 C4 C9 1.2(4) . . . . ?
C7 C8 C9 C4 1.8(3) . . . . ?
C7 C8 C9 C10 -178.7(2) . . . . ?
C3 C4 C9 C8 178.7(2) . . . . ?
C5 C4 C9 C8 -2.5(3) . . . . ?
C3 C4 C9 C10 -0.8(4) . . . . ?
C5 C4 C9 C10 178.0(2) . . . . ?
C11 C10 C9 C8 -177.6(2) . . . . ?
C11 C10 C9 C4 1.9(4) . . . . ?
Zn1 O1 C1 O2 156.41(16) . . . . ?
Zn1 O1 C1 C2 -25.7(3) . . . . ?
Zn1 O2 C1 O1 27.8(3) 1_455 . . . ?
Zn1 O2 C1 C2 -150.17(14) 1_455 . . . ?
O1 C1 C2 C3 149.4(2) . . . . ?
O2 C1 C2 C3 -32.6(3) . . . . ?
O1 C1 C2 C11 -31.7(3) . . . . ?
O2 C1 C2 C11 146.3(2) . . . . ?
C9 C10 C11 C2 -0.7(4) . . . . ?
C3 C2 C11 C10 -1.6(4) . . . . ?
C1 C2 C11 C10 179.6(2) . . . . ?
C11 C2 C3 C4 2.6(4) . . . . ?
C1 C2 C3 C4 -178.5(2) . . . . ?
C9 C4 C3 C2 -1.4(4) . . . . ?
C5 C4 C3 C2 179.8(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_compound2
_database_code_depnum_ccdc_archive 'CCDC 1481593'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H6 Cd N4 O3'
_chemical_formula_weight         366.62

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'
O O 0.0106 0.0060 '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'
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/a'

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

_cell_length_a                   10.2092(19)
_cell_length_b                   8.5034(17)
_cell_length_c                   13.885(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.655(5)
_cell_angle_gamma                90.00
_cell_volume                     1191.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2350
_cell_measurement_theta_min      0.698
_cell_measurement_theta_max      0.832

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.043
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             184
_exptl_absorpt_coefficient_mu    1.845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.698
_exptl_absorpt_correction_T_max  0.832
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.4 (release 27-04-2006 CrysAlis171 .NET)
(compiled Apr 27 2007,17:53:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_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  'Oxford Gemini S Ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9000
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2352
_reflns_number_gt                2043
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0235P)²+1.6729P] 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         2352
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0561
_refine_ls_wR_factor_gt          0.0526
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.003

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 0.625842(18) 0.49095(2) 0.134885(13) 0.01936(8) Uani 1 1 d . . .
O1W O 0.4636(2) 0.2971(3) 0.13451(16) 0.0431(6) Uani 1 1 d . . .
O2 O 0.7143(2) 0.8357(3) 0.76764(14) 0.0311(5) Uani 1 1 d . . .
N1 N 0.4493(2) 0.6609(3) 0.08921(17) 0.0228(5) Uani 1 1 d . . .
N2 N 0.3545(2) 0.6430(3) 0.01089(16) 0.0233(5) Uani 1 1 d . . .
O1 O 0.8326(2) 1.0041(2) 0.69887(15) 0.0333(5) Uani 1 1 d . . .
C7 C 0.4740(3) 0.8218(3) 0.2398(2) 0.0229(6) Uani 1 1 d . . .
C10 C 0.4980(3) 0.7056(4) 0.4994(2) 0.0253(6) Uani 1 1 d . . .
H10A H 0.4343 0.6267 0.4953 0.030 Uiso 1 1 calc R . .
C12 C 0.4031(3) 0.7709(3) 0.14374(19) 0.0205(6) Uani 1 1 d . . .
N4 N 0.2835(2) 0.8204(3) 0.10125(17) 0.0263(5) Uani 1 1 d . . .
C6 C 0.5702(3) 0.9433(4) 0.2464(2) 0.0279(6) Uani 1 1 d . . .
H6A H 0.5871 0.9944 0.1903 0.034 Uiso 1 1 calc R . .
C5 C 0.6380(3) 0.9851(3) 0.3349(2) 0.0262(6) Uani 1 1 d . . .
H5A H 0.6997 1.0662 0.3388 0.031 Uiso 1 1 calc R . .
C4 C 0.6156(3) 0.9066(3) 0.4207(2) 0.0208(6) Uani 1 1 d . . .
C2 C 0.6641(2) 0.8645(3) 0.59560(19) 0.0205(6) Uani 1 1 d . . .
N3 N 0.2563(2) 0.7384(3) 0.01801(16) 0.0276(6) Uani 1 1 d . . .
C3 C 0.6850(3) 0.9454(3) 0.5144(2) 0.0218(6) Uani 1 1 d . . .
H3A H 0.7457 1.0276 0.5204 0.026 Uiso 1 1 calc R . .
C11 C 0.5686(3) 0.7433(3) 0.5878(2) 0.0245(6) Uani 1 1 d . . .
H11A H 0.5538 0.6888 0.6432 0.029 Uiso 1 1 calc R . .
C1 C 0.7412(3) 0.9036(3) 0.6929(2) 0.0211(6) Uani 1 1 d . . .
C8 C 0.4496(3) 0.7463(3) 0.3216(2) 0.0252(6) Uani 1 1 d . . .
H8A H 0.3853 0.6680 0.3166 0.030 Uiso 1 1 calc R . .
C9 C 0.5204(3) 0.7852(3) 0.4141(2) 0.0208(6) 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
Cd1 O1 2.286(2) 2_646 ?
Cd1 N1 2.323(2) . ?
Cd1 O1W 2.336(2) . ?
Cd1 N2 2.357(2) 3_665 ?
Cd1 O2 2.361(2) 2_646 ?
Cd1 N4 2.368(2) 4_675 ?
Cd1 C1 2.672(3) 2_646 ?
O2 C1 1.254(3) . ?
O2 Cd1 2.361(2) 2_656 ?
N1 C12 1.333(3) . ?
N1 N2 1.351(3) . ?
N2 N3 1.305(3) . ?
N2 Cd1 2.357(2) 3_665 ?
O1 C1 1.259(3) . ?
O1 Cd1 2.286(2) 2_656 ?
C7 C8 1.360(4) . ?
C7 C6 1.418(4) . ?
C7 C12 1.483(4) . ?
C10 C11 1.365(4) . ?
C10 C9 1.412(4) . ?
C10 H10A 0.9300 . ?
C12 N4 1.341(3) . ?
N4 N3 1.343(3) . ?
N4 Cd1 2.368(2) 4_575 ?
C6 C5 1.363(4) . ?
C6 H6A 0.9300 . ?
C5 C4 1.414(4) . ?
C5 H5A 0.9300 . ?
C4 C9 1.411(4) . ?
C4 C3 1.424(4) . ?
C2 C3 1.364(4) . ?
C2 C11 1.412(4) . ?
C2 C1 1.495(4) . ?
C3 H3A 0.9300 . ?
C11 H11A 0.9300 . ?
C1 Cd1 2.672(3) 2_656 ?
C8 C9 1.416(4) . ?
C8 H8A 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 N1 105.30(8) 2_646 . ?
O1 Cd1 O1W 93.47(8) 2_646 . ?
N1 Cd1 O1W 85.28(9) . . ?
O1 Cd1 N2 149.74(8) 2_646 3_665 ?
N1 Cd1 N2 103.24(8) . 3_665 ?
O1W Cd1 N2 78.99(8) . 3_665 ?
O1 Cd1 O2 56.02(7) 2_646 2_646 ?
N1 Cd1 O2 161.00(8) . 2_646 ?
O1W Cd1 O2 92.03(8) . 2_646 ?
N2 Cd1 O2 94.66(7) 3_665 2_646 ?
O1 Cd1 N4 97.91(8) 2_646 4_675 ?
N1 Cd1 N4 92.71(8) . 4_675 ?
O1W Cd1 N4 168.57(8) . 4_675 ?
N2 Cd1 N4 90.56(8) 3_665 4_675 ?
O2 Cd1 N4 93.44(8) 2_646 4_675 ?
O1 Cd1 C1 28.06(8) 2_646 2_646 ?
N1 Cd1 C1 133.34(8) . 2_646 ?
O1W Cd1 C1 94.03(8) . 2_646 ?
N2 Cd1 C1 122.47(8) 3_665 2_646 ?
O2 Cd1 C1 27.98(8) 2_646 2_646 ?
N4 Cd1 C1 95.51(8) 4_675 2_646 ?
C1 O2 Cd1 89.93(16) . 2_656 ?
C12 N1 N2 105.3(2) . . ?
C12 N1 Cd1 127.42(18) . . ?
N2 N1 Cd1 125.58(17) . . ?
N3 N2 N1 109.5(2) . . ?
N3 N2 Cd1 122.07(16) . 3_665 ?
N1 N2 Cd1 127.05(16) . 3_665 ?
C1 O1 Cd1 93.25(17) . 2_656 ?
C8 C7 C6 120.1(3) . . ?
C8 C7 C12 119.1(3) . . ?
C6 C7 C12 120.7(3) . . ?
C11 C10 C9 120.7(3) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
N1 C12 N4 110.3(2) . . ?
N1 C12 C7 123.3(2) . . ?
N4 C12 C7 126.4(2) . . ?
N3 N4 C12 105.8(2) . . ?
N3 N4 Cd1 117.56(16) . 4_575 ?
C12 N4 Cd1 136.60(18) . 4_575 ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5A 119.6 . . ?
C4 C5 H5A 119.6 . . ?
C5 C4 C9 119.2(2) . . ?
C5 C4 C3 122.6(3) . . ?
C9 C4 C3 118.1(3) . . ?
C3 C2 C11 119.8(2) . . ?
C3 C2 C1 120.5(2) . . ?
C11 C2 C1 119.7(2) . . ?
N2 N3 N4 109.0(2) . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C10 C11 C2 120.4(3) . . ?
C10 C11 H11A 119.8 . . ?
C2 C11 H11A 119.8 . . ?
O2 C1 O1 120.7(2) . . ?
O2 C1 C2 119.7(2) . . ?
O1 C1 C2 119.6(2) . . ?
O2 C1 Cd1 62.08(14) . 2_656 ?
O1 C1 Cd1 58.69(14) . 2_656 ?
C2 C1 Cd1 176.62(19) . 2_656 ?
C7 C8 C9 121.0(3) . . ?
C7 C8 H8A 119.5 . . ?
C9 C8 H8A 119.5 . . ?
C4 C9 C10 119.6(2) . . ?
C4 C9 C8 118.8(3) . . ?
C10 C9 C8 121.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 Cd1 N1 C12 14.9(2) 2_646 . . . ?
O1W Cd1 N1 C12 107.3(2) . . . . ?
N2 Cd1 N1 C12 -175.2(2) 3_665 . . . ?
O2 Cd1 N1 C12 24.8(4) 2_646 . . . ?
N4 Cd1 N1 C12 -84.0(2) 4_675 . . . ?
C1 Cd1 N1 C12 16.2(3) 2_646 . . . ?
O1 Cd1 N1 N2 -148.2(2) 2_646 . . . ?
O1W Cd1 N1 N2 -55.8(2) . . . . ?
N2 Cd1 N1 N2 21.7(3) 3_665 . . . ?
O2 Cd1 N1 N2 -138.3(2) 2_646 . . . ?
N4 Cd1 N1 N2 112.9(2) 4_675 . . . ?
C1 Cd1 N1 N2 -146.93(19) 2_646 . . . ?
C12 N1 N2 N3 0.3(3) . . . . ?
Cd1 N1 N2 N3 166.41(18) . . . . ?
C12 N1 N2 Cd1 167.09(18) . . . 3_665 ?
Cd1 N1 N2 Cd1 -26.8(3) . . . 3_665 ?
N2 N1 C12 N4 0.0(3) . . . . ?
Cd1 N1 C12 N4 -165.83(19) . . . . ?
N2 N1 C12 C7 177.1(3) . . . . ?
Cd1 N1 C12 C7 11.3(4) . . . . ?
C8 C7 C12 N1 -90.1(3) . . . . ?
C6 C7 C12 N1 87.3(4) . . . . ?
C8 C7 C12 N4 86.6(4) . . . . ?
C6 C7 C12 N4 -96.0(4) . . . . ?
N1 C12 N4 N3 -0.2(3) . . . . ?
C7 C12 N4 N3 -177.2(3) . . . . ?
N1 C12 N4 Cd1 -178.2(2) . . . 4_575 ?
C7 C12 N4 Cd1 4.8(5) . . . 4_575 ?
C8 C7 C6 C5 -0.3(4) . . . . ?
C12 C7 C6 C5 -177.7(3) . . . . ?
C7 C6 C5 C4 1.2(4) . . . . ?
C6 C5 C4 C9 -0.9(4) . . . . ?
C6 C5 C4 C3 179.4(3) . . . . ?
N1 N2 N3 N4 -0.4(3) . . . . ?
Cd1 N2 N3 N4 -168.01(18) 3_665 . . . ?
C12 N4 N3 N2 0.4(3) . . . . ?
Cd1 N4 N3 N2 178.82(18) 4_575 . . . ?
C11 C2 C3 C4 -2.3(4) . . . . ?
C1 C2 C3 C4 178.0(2) . . . . ?
C5 C4 C3 C2 -178.0(3) . . . . ?
C9 C4 C3 C2 2.3(4) . . . . ?
C9 C10 C11 C2 1.0(4) . . . . ?
C3 C2 C11 C10 0.6(4) . . . . ?
C1 C2 C11 C10 -179.6(3) . . . . ?
Cd1 O2 C1 O1 3.4(3) 2_656 . . . ?
Cd1 O2 C1 C2 -176.7(2) 2_656 . . . ?
Cd1 O1 C1 O2 -3.6(3) 2_656 . . . ?
Cd1 O1 C1 C2 176.6(2) 2_656 . . . ?
C3 C2 C1 O2 175.0(3) . . . . ?
C11 C2 C1 O2 -4.7(4) . . . . ?
C3 C2 C1 O1 -5.2(4) . . . . ?
C11 C2 C1 O1 175.1(3) . . . . ?
C3 C2 C1 Cd1 54(3) . . . 2_656 ?
C11 C2 C1 Cd1 -125(3) . . . 2_656 ?
C6 C7 C8 C9 -1.0(4) . . . . ?
C12 C7 C8 C9 176.4(2) . . . . ?
C5 C4 C9 C10 179.7(3) . . . . ?
C3 C4 C9 C10 -0.6(4) . . . . ?
C5 C4 C9 C8 -0.4(4) . . . . ?
C3 C4 C9 C8 179.3(2) . . . . ?
C11 C10 C9 C4 -1.0(4) . . . . ?
C11 C10 C9 C8 179.1(3) . . . . ?
C7 C8 C9 C4 1.3(4) . . . . ?
C7 C8 C9 C10 -178.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.075



#end
####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1489693'
_audit_update_record             
;
2016-07-03 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;
_audit_creation_date             2016-06-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.08.17 svn.r3210 for OlexSys, GUI svn.r5083)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 N4 O2, H2 O'
_chemical_formula_sum            'C12 H10 N4 O3'
_chemical_formula_weight         258.24
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.018(2)
_cell_length_b                   5.4970(11)
_cell_length_c                   43.932(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.58(3)
_cell_angle_gamma                90
_cell_volume                     2419.2(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1072
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.997
_cell_measurement_theta_min      0.992
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0755
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            8778
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.688
_diffrn_reflns_theta_min         0.927
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'bleam 17b'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.688
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2313
_reflns_number_total             5333
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0623
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1359P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1911
_refine_ls_wR_factor_ref         0.2378
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B), O6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 N007(H007), N008(H008), C3(H3), C4(H4), C20(H20), C18(H18), C6(H6), C17(H17),
 C22(H22), C23(H23), C8(H8), C15(H15), C9(H9), C11(H11)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.2229(3) 0.1953(4) 0.27077(5) 0.0350(7) Uani 1 1 d . . . . .
H5A H 0.2881 0.1085 0.2768 0.053 Uiso 1 1 d G . . . .
H5B H 0.1756 0.1147 0.2581 0.053 Uiso 1 1 d G . . . .
O2 O 0.6242(2) 0.7083(4) 0.49272(4) 0.0296(6) Uani 1 1 d . . . . .
O3 O 0.8758(2) 0.2920(4) 0.50732(4) 0.0294(6) Uani 1 1 d . . . . .
O6 O 1.2771(3) 0.8049(4) 0.72929(5) 0.0337(6) Uani 1 1 d . . . . .
H6A H 1.3235 0.8872 0.7419 0.051 Uiso 1 1 d G . . . .
H6B H 1.2167 0.8949 0.7215 0.051 Uiso 1 1 d G . . . .
O1 O 0.6821(2) 0.3672(4) 0.46541(5) 0.0305(6) Uani 1 1 d . . . . .
H1 H 0.7453 0.3663 0.4774 0.046 Uiso 1 1 calc GR . . . .
O4 O 0.8172(2) 0.6323(4) 0.53464(4) 0.0310(6) Uani 1 1 d . . . . .
H4A H 0.7740 0.6621 0.5191 0.047 Uiso 1 1 calc GR . . . .
N007 N 1.4244(3) 0.4288(5) 0.70180(5) 0.0248(7) Uani 1 1 d . . . . .
H007 H 1.3818 0.5579 0.7070 0.030 Uiso 1 1 calc R . . . .
N008 N 0.0754(3) 0.5697(4) 0.29814(5) 0.0222(6) Uani 1 1 d . . . . .
H008 H 0.1172 0.4396 0.2930 0.027 Uiso 1 1 calc R . . . .
N009 N 1.5259(3) 0.3208(5) 0.71823(5) 0.0278(7) Uani 1 1 d . . . . .
N00A N 0.0114(3) 0.8950(5) 0.32437(5) 0.0257(7) Uani 1 1 d . . . . .
N00B N 1.4883(3) 0.1038(5) 0.67556(5) 0.0253(6) Uani 1 1 d . . . . .
N00C N -0.0638(3) 0.8734(5) 0.29756(5) 0.0291(7) Uani 1 1 d . . . . .
N00D N 1.5634(3) 0.1263(5) 0.70232(5) 0.0281(7) Uani 1 1 d . . . . .
N00E N -0.0260(3) 0.6799(5) 0.28156(5) 0.0281(7) Uani 1 1 d . . . . .
C16 C 1.1893(3) 0.2592(5) 0.60145(6) 0.0191(7) Uani 1 1 d . . . . .
C5 C 0.3946(3) 0.5255(5) 0.39548(6) 0.0172(7) Uani 1 1 d . . . . .
C3 C 0.2830(3) 0.4280(6) 0.34591(6) 0.0230(7) Uani 1 1 d . . . . .
H3 H 0.2733 0.3275 0.3290 0.028 Uiso 1 1 calc R . . . .
C7 C 0.5061(3) 0.6243(6) 0.44506(6) 0.0189(7) Uani 1 1 d . . . . .
C12 C 0.6103(3) 0.5665(6) 0.46958(6) 0.0199(7) Uani 1 1 d . . . . .
C10 C 0.3104(3) 0.7424(5) 0.39852(6) 0.0171(7) Uani 1 1 d . . . . .
C21 C 1.1058(3) 0.4740(5) 0.60457(6) 0.0186(7) Uani 1 1 d . . . . .
C4 C 0.3789(3) 0.3703(5) 0.36866(6) 0.0194(7) Uani 1 1 d . . . . .
H4 H 0.4323 0.2330 0.3665 0.023 Uiso 1 1 calc R . . . .
C20 C 1.0072(3) 0.5291(5) 0.58076(6) 0.0196(7) Uani 1 1 d . . . . .
H20 H 0.9532 0.6658 0.5826 0.024 Uiso 1 1 calc R . . . .
C14 C 1.3004(3) 0.3578(6) 0.65109(6) 0.0186(7) Uani 1 1 d . . . . .
C18 C 1.0780(3) 0.1607(6) 0.55191(6) 0.0250(7) Uani 1 1 d . . . . .
H18 H 1.0685 0.0605 0.5350 0.030 Uiso 1 1 calc R . . . .
C19 C 0.9933(3) 0.3756(6) 0.55495(6) 0.0184(7) Uani 1 1 d . . . . .
C6 C 0.4924(3) 0.4715(5) 0.41921(6) 0.0198(7) Uani 1 1 d . . . . .
H6 H 0.5467 0.3351 0.4174 0.024 Uiso 1 1 calc R . . . .
C17 C 1.1737(3) 0.1045(6) 0.57450(6) 0.0227(7) Uani 1 1 d . . . . .
H17 H 1.2276 -0.0320 0.5723 0.027 Uiso 1 1 calc R . . . .
C1 C 0.0982(3) 0.7035(5) 0.32428(6) 0.0184(7) Uani 1 1 d . . . . .
C2 C 0.1995(3) 0.6431(6) 0.34873(6) 0.0189(7) Uani 1 1 d . . . . .
C22 C 1.1212(3) 0.6298(6) 0.63144(6) 0.0230(7) Uani 1 1 d . . . . .
H22 H 1.0672 0.7661 0.6336 0.028 Uiso 1 1 calc R . . . .
C24 C 0.8893(3) 0.4331(6) 0.53045(6) 0.0206(7) Uani 1 1 d . . . . .
C13 C 1.4022(3) 0.2949(5) 0.67555(6) 0.0207(7) Uani 1 1 d . . . . .
C23 C 1.2163(3) 0.5750(5) 0.65382(6) 0.0217(7) Uani 1 1 d . . . . .
H23 H 1.2264 0.6769 0.6706 0.026 Uiso 1 1 calc R . . . .
C8 C 0.4223(3) 0.8401(6) 0.44807(6) 0.0214(7) Uani 1 1 d . . . . .
H8 H 0.4323 0.9406 0.4650 0.026 Uiso 1 1 calc R . . . .
C15 C 1.2872(3) 0.2039(5) 0.62535(6) 0.0198(7) Uani 1 1 d . . . . .
H15 H 1.3411 0.0669 0.6237 0.024 Uiso 1 1 calc R . . . .
C9 C 0.3263(3) 0.8969(6) 0.42543(6) 0.0230(7) Uani 1 1 d . . . . .
H9 H 0.2727 1.0337 0.4276 0.028 Uiso 1 1 calc R . . . .
C11 C 0.2127(3) 0.7962(5) 0.37452(6) 0.0198(7) Uani 1 1 d . . . . .
H11 H 0.1584 0.9327 0.3762 0.024 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
O5 H5A 0.8498 . ?
O5 H5B 0.8500 . ?
O2 C12 1.287(3) . ?
O3 C24 1.285(3) . ?
O6 H6A 0.8505 . ?
O6 H6B 0.8501 . ?
O1 H1 0.8200 . ?
O1 C12 1.325(4) . ?
O4 H4A 0.8200 . ?
O4 C24 1.325(4) . ?
N007 H007 0.8600 . ?
N007 N009 1.375(3) . ?
N007 C13 1.384(3) . ?
N008 H008 0.8600 . ?
N008 N00E 1.384(3) . ?
N008 C1 1.381(3) . ?
N009 N00D 1.333(3) . ?
N00A N00C 1.397(3) . ?
N00A C1 1.365(4) . ?
N00B N00D 1.395(3) . ?
N00B C13 1.359(4) . ?
N00C N00E 1.332(3) . ?
C16 C21 1.454(4) . ?
C16 C17 1.465(4) . ?
C16 C15 1.461(4) . ?
C5 C10 1.467(4) . ?
C5 C4 1.462(4) . ?
C5 C6 1.454(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.416(4) . ?
C3 C2 1.454(4) . ?
C7 C12 1.526(4) . ?
C7 C6 1.418(4) . ?
C7 C8 1.460(4) . ?
C10 C9 1.463(4) . ?
C10 C11 1.462(4) . ?
C21 C20 1.463(4) . ?
C21 C22 1.465(4) . ?
C4 H4 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.419(4) . ?
C14 C13 1.514(4) . ?
C14 C23 1.467(4) . ?
C14 C15 1.417(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.461(4) . ?
C18 C17 1.408(4) . ?
C19 C24 1.524(4) . ?
C6 H6 0.9300 . ?
C17 H17 0.9300 . ?
C1 C2 1.507(4) . ?
C2 C11 1.416(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.394(4) . ?
C23 H23 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.412(4) . ?
C15 H15 0.9300 . ?
C9 H9 0.9300 . ?
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
H5A O5 H5B 109.4 . . ?
H6A O6 H6B 109.5 . . ?
C12 O1 H1 109.5 . . ?
C24 O4 H4A 109.5 . . ?
N009 N007 H007 125.7 . . ?
N009 N007 C13 108.6(2) . . ?
C13 N007 H007 125.7 . . ?
N00E N008 H008 125.7 . . ?
C1 N008 H008 125.7 . . ?
C1 N008 N00E 108.6(2) . . ?
N00D N009 N007 106.4(2) . . ?
C1 N00A N00C 105.7(2) . . ?
C13 N00B N00D 105.6(2) . . ?
N00E N00C N00A 111.0(2) . . ?
N009 N00D N00B 111.1(2) . . ?
N00C N00E N008 106.4(2) . . ?
C21 C16 C17 119.4(3) . . ?
C21 C16 C15 118.9(2) . . ?
C15 C16 C17 121.7(3) . . ?
C4 C5 C10 119.4(2) . . ?
C6 C5 C10 119.0(2) . . ?
C6 C5 C4 121.6(3) . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C6 C7 C12 120.1(3) . . ?
C6 C7 C8 120.2(3) . . ?
C8 C7 C12 119.7(2) . . ?
O2 C12 O1 123.7(3) . . ?
O2 C12 C7 120.0(3) . . ?
O1 C12 C7 116.3(2) . . ?
C9 C10 C5 119.2(3) . . ?
C11 C10 C5 118.7(2) . . ?
C11 C10 C9 122.1(3) . . ?
C16 C21 C20 119.0(2) . . ?
C16 C21 C22 119.6(3) . . ?
C22 C21 C20 121.3(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.8 . . ?
C21 C20 H20 119.7 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.7 . . ?
C23 C14 C13 120.7(2) . . ?
C15 C14 C13 119.1(3) . . ?
C15 C14 C23 120.1(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.3(3) . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 C24 120.1(3) . . ?
C18 C19 C24 119.8(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
N008 C1 C2 125.4(3) . . ?
N00A C1 N008 108.3(2) . . ?
N00A C1 C2 126.3(2) . . ?
C3 C2 C1 120.2(2) . . ?
C11 C2 C3 120.1(3) . . ?
C11 C2 C1 119.7(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 H22 119.8 . . ?
O3 C24 O4 123.8(3) . . ?
O3 C24 C19 119.9(3) . . ?
O4 C24 C19 116.3(2) . . ?
N007 C13 C14 124.8(3) . . ?
N00B C13 N007 108.3(2) . . ?
N00B C13 C14 126.8(3) . . ?
C14 C23 H23 119.8 . . ?
C22 C23 C14 120.4(3) . . ?
C22 C23 H23 119.8 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.9 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C10 C9 H9 119.7 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C11 H11 119.6 . . ?
C2 C11 C10 120.8(3) . . ?
C2 C11 H11 119.6 . . ?

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
N007 N009 N00D N00B 0.0(4) . . . . ?
N008 C1 C2 C3 -0.1(5) . . . . ?
N008 C1 C2 C11 -179.9(3) . . . . ?
N009 N007 C13 N00B 0.4(4) . . . . ?
N009 N007 C13 C14 -178.6(3) . . . . ?
N00A N00C N00E N008 0.5(4) . . . . ?
N00A C1 C2 C3 178.2(3) . . . . ?
N00A C1 C2 C11 -1.6(5) . . . . ?
N00C N00A C1 N008 -0.2(3) . . . . ?
N00C N00A C1 C2 -178.8(3) . . . . ?
N00D N00B C13 N007 -0.4(3) . . . . ?
N00D N00B C13 C14 178.6(3) . . . . ?
N00E N008 C1 N00A 0.5(3) . . . . ?
N00E N008 C1 C2 179.1(3) . . . . ?
C16 C21 C20 C19 -0.1(4) . . . . ?
C16 C21 C22 C23 0.8(5) . . . . ?
C5 C10 C9 C8 0.7(5) . . . . ?
C5 C10 C11 C2 -0.3(4) . . . . ?
C3 C2 C11 C10 0.5(5) . . . . ?
C7 C8 C9 C10 -0.7(5) . . . . ?
C12 C7 C6 C5 -179.3(3) . . . . ?
C12 C7 C8 C9 179.5(3) . . . . ?
C10 C5 C4 C3 -0.3(4) . . . . ?
C10 C5 C6 C7 0.5(4) . . . . ?
C21 C16 C17 C18 -0.7(5) . . . . ?
C21 C16 C15 C14 -0.1(4) . . . . ?
C21 C20 C19 C18 -0.1(5) . . . . ?
C21 C20 C19 C24 179.3(3) . . . . ?
C21 C22 C23 C14 -1.3(5) . . . . ?
C4 C5 C10 C9 179.9(3) . . . . ?
C4 C5 C10 C11 0.2(4) . . . . ?
C4 C5 C6 C7 -180.0(3) . . . . ?
C4 C3 C2 C1 179.7(3) . . . . ?
C4 C3 C2 C11 -0.6(5) . . . . ?
C20 C21 C22 C23 -179.6(3) . . . . ?
C20 C19 C24 O3 -179.1(3) . . . . ?
C20 C19 C24 O4 1.2(4) . . . . ?
C18 C19 C24 O3 0.3(5) . . . . ?
C18 C19 C24 O4 -179.4(3) . . . . ?
C19 C18 C17 C16 0.5(5) . . . . ?
C6 C5 C10 C9 -0.6(4) . . . . ?
C6 C5 C10 C11 179.7(3) . . . . ?
C6 C5 C4 C3 -179.9(3) . . . . ?
C6 C7 C12 O2 178.6(3) . . . . ?
C6 C7 C12 O1 -1.5(4) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C17 C16 C21 C20 0.6(4) . . . . ?
C17 C16 C21 C22 -179.8(3) . . . . ?
C17 C16 C15 C14 179.7(3) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
C17 C18 C19 C24 -179.5(3) . . . . ?
C1 N008 N00E N00C -0.6(3) . . . . ?
C1 N00A N00C N00E -0.2(4) . . . . ?
C1 C2 C11 C10 -179.8(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C22 C21 C20 C19 -179.7(3) . . . . ?
C13 N007 N009 N00D -0.3(3) . . . . ?
C13 N00B N00D N009 0.2(4) . . . . ?
C13 C14 C23 C22 -179.0(3) . . . . ?
C13 C14 C15 C16 179.7(3) . . . . ?
C23 C14 C13 N007 0.5(5) . . . . ?
C23 C14 C13 N00B -178.3(3) . . . . ?
C23 C14 C15 C16 -0.4(5) . . . . ?
C8 C7 C12 O2 -0.2(4) . . . . ?
C8 C7 C12 O1 179.7(3) . . . . ?
C8 C7 C6 C5 -0.5(5) . . . . ?
C15 C16 C21 C20 -179.7(3) . . . . ?
C15 C16 C21 C22 0.0(4) . . . . ?
C15 C16 C17 C18 179.5(3) . . . . ?
C15 C14 C13 N007 -179.6(3) . . . . ?
C15 C14 C13 N00B 1.6(5) . . . . ?
C15 C14 C23 C22 1.1(5) . . . . ?
C9 C10 C11 C2 -179.9(3) . . . . ?
C11 C10 C9 C8 -179.6(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
