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

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

data_z
_database_code_depnum_ccdc_archive 'CCDC 1036881'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N3 O4'
_chemical_formula_weight         299.28

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           tetragonal
_symmetry_space_group_name_H-M   P4/n

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

_cell_length_a                   19.7660(14)
_cell_length_b                   19.7660(14)
_cell_length_c                   7.7429(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3025.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9546
_exptl_absorpt_correction_T_max  0.9657
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33852
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2673
_reflns_number_gt                2412
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0467P)²+0.9894P] 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         2673
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.68423(6) 0.40024(6) 0.2231(2) 0.0692(4) Uani 1 1 d . . .
O2 O 0.58770(5) 0.43021(5) 0.35704(16) 0.0548(3) Uani 1 1 d . . .
O3 O 0.54569(5) 0.35329(6) 0.01357(15) 0.0540(3) Uani 1 1 d . . .
O4 O 0.66404(5) 0.27017(5) 0.29992(15) 0.0508(3) Uani 1 1 d . . .
N1 N 0.47264(8) 0.14275(8) 0.1202(2) 0.0732(5) Uani 1 1 d . . .
N2 N 0.45145(6) 0.35503(6) 0.18581(18) 0.0488(3) Uani 1 1 d . . .
H2B H 0.4246 0.3768 0.1183 0.059 Uiso 1 1 calc R . .
N3 N 0.67244(6) 0.16653(6) 0.18264(19) 0.0548(4) Uani 1 1 d . . .
H3B H 0.7155 0.1705 0.1958 0.066 Uiso 1 1 calc R . .
H3C H 0.6559 0.1303 0.1378 0.066 Uiso 1 1 calc R . .
C1 C 0.37455(8) 0.34443(9) 0.4422(3) 0.0591(4) Uani 1 1 d . . .
H1A H 0.3388 0.3682 0.3930 0.071 Uiso 1 1 calc R . .
C2 C 0.37033(9) 0.31881(9) 0.6079(3) 0.0645(5) Uani 1 1 d . . .
H2A H 0.3308 0.3251 0.6709 0.077 Uiso 1 1 calc R . .
C3 C 0.42324(10) 0.28429(9) 0.6815(3) 0.0620(5) Uani 1 1 d . . .
H3A H 0.4195 0.2682 0.7940 0.074 Uiso 1 1 calc R . .
C4 C 0.48224(8) 0.27332(8) 0.5892(2) 0.0527(4) Uani 1 1 d . . .
H4A H 0.5181 0.2499 0.6389 0.063 Uiso 1 1 calc R . .
C5 C 0.48707(7) 0.29747(7) 0.4236(2) 0.0416(3) Uani 1 1 d . . .
C6 C 0.43391(7) 0.33341(7) 0.3525(2) 0.0448(4) Uani 1 1 d . . .
C7 C 0.51558(7) 0.33756(7) 0.1440(2) 0.0407(3) Uani 1 1 d . . .
C8 C 0.54376(7) 0.29338(6) 0.29310(19) 0.0385(3) Uani 1 1 d . . .
C9 C 0.56329(7) 0.22344(7) 0.2292(2) 0.0413(3) Uani 1 1 d . . .
C10 C 0.63171(7) 0.21623(7) 0.2315(2) 0.0420(3) Uani 1 1 d . . .
C11 C 0.61386(7) 0.31728(7) 0.3606(2) 0.0421(3) Uani 1 1 d . . .
H11A H 0.6133 0.3162 0.4871 0.051 Uiso 1 1 calc R . .
C12 C 0.63424(7) 0.38717(7) 0.3030(2) 0.0458(4) Uani 1 1 d . . .
C13 C 0.59417(10) 0.50142(8) 0.3113(3) 0.0753(6) Uani 1 1 d . . .
H13A H 0.6118 0.5267 0.4089 0.090 Uiso 1 1 calc R . .
H13B H 0.6255 0.5064 0.2157 0.090 Uiso 1 1 calc R . .
C14 C 0.52820(11) 0.52778(10) 0.2628(3) 0.0855(7) Uani 1 1 d . . .
H14A H 0.5323 0.5748 0.2334 0.128 Uiso 1 1 calc R . .
H14B H 0.4974 0.5228 0.3579 0.128 Uiso 1 1 calc R . .
H14C H 0.5113 0.5031 0.1651 0.128 Uiso 1 1 calc R . .
C15 C 0.51517(8) 0.17741(7) 0.1669(2) 0.0480(4) 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
O1 C12 1.1939(19) . ?
O2 C12 1.3211(17) . ?
O2 C13 1.457(2) . ?
O3 C7 1.2128(18) . ?
O4 C10 1.3513(17) . ?
O4 C11 1.4392(16) . ?
N1 C15 1.143(2) . ?
N2 C7 1.3530(18) . ?
N2 C6 1.403(2) . ?
N2 H2B 0.8600 . ?
N3 C10 1.3254(18) . ?
N3 H3B 0.8600 . ?
N3 H3C 0.8600 . ?
C1 C6 1.381(2) . ?
C1 C2 1.382(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.373(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.385(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.371(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.383(2) . ?
C5 C8 1.511(2) . ?
C7 C8 1.551(2) . ?
C8 C9 1.5182(18) . ?
C8 C11 1.5542(19) . ?
C9 C10 1.360(2) . ?
C9 C15 1.402(2) . ?
C11 C12 1.506(2) . ?
C11 H11A 0.9800 . ?
C13 C14 1.454(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C12 O2 C13 118.95(13) . . ?
C10 O4 C11 108.21(10) . . ?
C7 N2 C6 111.96(12) . . ?
C7 N2 H2B 124.0 . . ?
C6 N2 H2B 124.0 . . ?
C10 N3 H3B 120.0 . . ?
C10 N3 H3C 120.0 . . ?
H3B N3 H3C 120.0 . . ?
C6 C1 C2 117.43(16) . . ?
C6 C1 H1A 121.3 . . ?
C2 C1 H1A 121.3 . . ?
C3 C2 C1 121.46(16) . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C2 C3 C4 120.33(17) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 119.11(16) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 119.90(14) . . ?
C4 C5 C8 131.17(13) . . ?
C6 C5 C8 108.92(13) . . ?
C1 C6 C5 121.74(16) . . ?
C1 C6 N2 128.67(15) . . ?
C5 C6 N2 109.59(12) . . ?
O3 C7 N2 126.41(14) . . ?
O3 C7 C8 126.01(12) . . ?
N2 C7 C8 107.58(12) . . ?
C5 C8 C9 117.07(11) . . ?
C5 C8 C7 101.62(11) . . ?
C9 C8 C7 111.19(12) . . ?
C5 C8 C11 114.83(12) . . ?
C9 C8 C11 99.18(10) . . ?
C7 C8 C11 113.53(11) . . ?
C10 C9 C15 127.67(13) . . ?
C10 C9 C8 110.13(12) . . ?
C15 C9 C8 122.04(12) . . ?
N3 C10 O4 114.17(12) . . ?
N3 C10 C9 132.70(14) . . ?
O4 C10 C9 113.12(12) . . ?
O4 C11 C12 108.20(12) . . ?
O4 C11 C8 107.94(10) . . ?
C12 C11 C8 114.68(12) . . ?
O4 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C8 C11 H11A 108.6 . . ?
O1 C12 O2 126.94(14) . . ?
O1 C12 C11 124.97(13) . . ?
O2 C12 C11 108.09(13) . . ?
C14 C13 O2 109.29(16) . . ?
C14 C13 H13A 109.8 . . ?
O2 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
O2 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C9 175.39(17) . . ?

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
C6 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C3 C4 C5 C8 -179.85(15) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C2 C1 C6 N2 -178.54(16) . . . . ?
C4 C5 C6 C1 -1.7(2) . . . . ?
C8 C5 C6 C1 179.15(14) . . . . ?
C4 C5 C6 N2 177.68(13) . . . . ?
C8 C5 C6 N2 -1.42(16) . . . . ?
C7 N2 C6 C1 176.78(16) . . . . ?
C7 N2 C6 C5 -2.59(17) . . . . ?
C6 N2 C7 O3 -174.89(14) . . . . ?
C6 N2 C7 C8 5.31(16) . . . . ?
C4 C5 C8 C9 64.0(2) . . . . ?
C6 C5 C8 C9 -117.08(14) . . . . ?
C4 C5 C8 C7 -174.74(15) . . . . ?
C6 C5 C8 C7 4.22(14) . . . . ?
C4 C5 C8 C11 -51.8(2) . . . . ?
C6 C5 C8 C11 127.20(13) . . . . ?
O3 C7 C8 C5 174.51(14) . . . . ?
N2 C7 C8 C5 -5.69(14) . . . . ?
O3 C7 C8 C9 -60.17(18) . . . . ?
N2 C7 C8 C9 119.62(13) . . . . ?
O3 C7 C8 C11 50.65(19) . . . . ?
N2 C7 C8 C11 -129.55(12) . . . . ?
C5 C8 C9 C10 -133.71(14) . . . . ?
C7 C8 C9 C10 110.14(14) . . . . ?
C11 C8 C9 C10 -9.63(16) . . . . ?
C5 C8 C9 C15 50.5(2) . . . . ?
C7 C8 C9 C15 -65.61(18) . . . . ?
C11 C8 C9 C15 174.62(15) . . . . ?
C11 O4 C10 N3 -175.08(14) . . . . ?
C11 O4 C10 C9 3.89(18) . . . . ?
C15 C9 C10 N3 -1.5(3) . . . . ?
C8 C9 C10 N3 -176.99(17) . . . . ?
C15 C9 C10 O4 179.74(15) . . . . ?
C8 C9 C10 O4 4.29(18) . . . . ?
C10 O4 C11 C12 -134.84(13) . . . . ?
C10 O4 C11 C8 -10.20(16) . . . . ?
C5 C8 C11 O4 137.29(12) . . . . ?
C9 C8 C11 O4 11.65(15) . . . . ?
C7 C8 C11 O4 -106.38(13) . . . . ?
C5 C8 C11 C12 -102.04(15) . . . . ?
C9 C8 C11 C12 132.32(13) . . . . ?
C7 C8 C11 C12 14.30(17) . . . . ?
C13 O2 C12 O1 3.0(3) . . . . ?
C13 O2 C12 C11 -177.42(15) . . . . ?
O4 C11 C12 O1 -1.1(2) . . . . ?
C8 C11 C12 O1 -121.62(17) . . . . ?
O4 C11 C12 O2 179.28(12) . . . . ?
C8 C11 C12 O2 58.75(17) . . . . ?
C12 O2 C13 C14 137.98(19) . . . . ?
C10 C9 C15 N1 175(2) . . . . ?
C8 C9 C15 N1 -10(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.031


# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.250 0.060 138 30 ' '
2 0.750 0.750 -0.060 138 30 ' '
_platon_squeeze_details          
;
;


####################################################################### 
# 
# 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_z_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1899658'
loop_
_audit_author_name
_audit_author_address
'Teng Shenghan'
;East China Normal University
China
;
_audit_update_record             
;
2019-07-16 deposited with the CCDC.	2019-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N3 O4'
_chemical_formula_weight         299.28

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           tetragonal
_symmetry_space_group_name_H-M   P4/n

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

_cell_length_a                   19.7660(14)
_cell_length_b                   19.7660(14)
_cell_length_c                   7.7429(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3025.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9546
_exptl_absorpt_correction_T_max  0.9657
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33852
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2673
_reflns_number_gt                2412
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0467P)²+0.9894P] 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         2673
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0976
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.68423(6) 0.40024(6) 0.2231(2) 0.0692(4) Uani 1 1 d . . .
O2 O 0.58770(5) 0.43021(5) 0.35704(16) 0.0548(3) Uani 1 1 d . . .
O3 O 0.54569(5) 0.35329(6) 0.01357(15) 0.0540(3) Uani 1 1 d . . .
O4 O 0.66404(5) 0.27017(5) 0.29992(15) 0.0508(3) Uani 1 1 d . . .
N1 N 0.47264(8) 0.14275(8) 0.1202(2) 0.0732(5) Uani 1 1 d . . .
N2 N 0.45145(6) 0.35503(6) 0.18581(18) 0.0488(3) Uani 1 1 d . . .
H2B H 0.4246 0.3768 0.1183 0.059 Uiso 1 1 calc R . .
N3 N 0.67244(6) 0.16653(6) 0.18264(19) 0.0548(4) Uani 1 1 d . . .
H3B H 0.7155 0.1705 0.1958 0.066 Uiso 1 1 calc R . .
H3C H 0.6559 0.1303 0.1378 0.066 Uiso 1 1 calc R . .
C1 C 0.37455(8) 0.34443(9) 0.4422(3) 0.0591(4) Uani 1 1 d . . .
H1A H 0.3388 0.3682 0.3930 0.071 Uiso 1 1 calc R . .
C2 C 0.37033(9) 0.31881(9) 0.6079(3) 0.0645(5) Uani 1 1 d . . .
H2A H 0.3308 0.3251 0.6709 0.077 Uiso 1 1 calc R . .
C3 C 0.42324(10) 0.28429(9) 0.6815(3) 0.0620(5) Uani 1 1 d . . .
H3A H 0.4195 0.2682 0.7940 0.074 Uiso 1 1 calc R . .
C4 C 0.48224(8) 0.27332(8) 0.5892(2) 0.0527(4) Uani 1 1 d . . .
H4A H 0.5181 0.2499 0.6389 0.063 Uiso 1 1 calc R . .
C5 C 0.48707(7) 0.29747(7) 0.4236(2) 0.0416(3) Uani 1 1 d . . .
C6 C 0.43391(7) 0.33341(7) 0.3525(2) 0.0448(4) Uani 1 1 d . . .
C7 C 0.51558(7) 0.33756(7) 0.1440(2) 0.0407(3) Uani 1 1 d . . .
C8 C 0.54376(7) 0.29338(6) 0.29310(19) 0.0385(3) Uani 1 1 d . . .
C9 C 0.56329(7) 0.22344(7) 0.2292(2) 0.0413(3) Uani 1 1 d . . .
C10 C 0.63171(7) 0.21623(7) 0.2315(2) 0.0420(3) Uani 1 1 d . . .
C11 C 0.61386(7) 0.31728(7) 0.3606(2) 0.0421(3) Uani 1 1 d . . .
H11A H 0.6133 0.3162 0.4871 0.051 Uiso 1 1 calc R . .
C12 C 0.63424(7) 0.38717(7) 0.3030(2) 0.0458(4) Uani 1 1 d . . .
C13 C 0.59417(10) 0.50142(8) 0.3113(3) 0.0753(6) Uani 1 1 d . . .
H13A H 0.6118 0.5267 0.4089 0.090 Uiso 1 1 calc R . .
H13B H 0.6255 0.5064 0.2157 0.090 Uiso 1 1 calc R . .
C14 C 0.52820(11) 0.52778(10) 0.2628(3) 0.0855(7) Uani 1 1 d . . .
H14A H 0.5323 0.5748 0.2334 0.128 Uiso 1 1 calc R . .
H14B H 0.4974 0.5228 0.3579 0.128 Uiso 1 1 calc R . .
H14C H 0.5113 0.5031 0.1651 0.128 Uiso 1 1 calc R . .
C15 C 0.51517(8) 0.17741(7) 0.1669(2) 0.0480(4) 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
O1 C12 1.1939(19) . ?
O2 C12 1.3211(17) . ?
O2 C13 1.457(2) . ?
O3 C7 1.2128(18) . ?
O4 C10 1.3513(17) . ?
O4 C11 1.4392(16) . ?
N1 C15 1.143(2) . ?
N2 C7 1.3530(18) . ?
N2 C6 1.403(2) . ?
N2 H2B 0.8600 . ?
N3 C10 1.3254(18) . ?
N3 H3B 0.8600 . ?
N3 H3C 0.8600 . ?
C1 C6 1.381(2) . ?
C1 C2 1.382(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.373(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.385(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.371(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.383(2) . ?
C5 C8 1.511(2) . ?
C7 C8 1.551(2) . ?
C8 C9 1.5182(18) . ?
C8 C11 1.5542(19) . ?
C9 C10 1.360(2) . ?
C9 C15 1.402(2) . ?
C11 C12 1.506(2) . ?
C11 H11A 0.9800 . ?
C13 C14 1.454(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C12 O2 C13 118.95(13) . . ?
C10 O4 C11 108.21(10) . . ?
C7 N2 C6 111.96(12) . . ?
C7 N2 H2B 124.0 . . ?
C6 N2 H2B 124.0 . . ?
C10 N3 H3B 120.0 . . ?
C10 N3 H3C 120.0 . . ?
H3B N3 H3C 120.0 . . ?
C6 C1 C2 117.43(16) . . ?
C6 C1 H1A 121.3 . . ?
C2 C1 H1A 121.3 . . ?
C3 C2 C1 121.46(16) . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C2 C3 C4 120.33(17) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 119.11(16) . . ?
C5 C4 H4A 120.4 . . ?
C3 C4 H4A 120.4 . . ?
C4 C5 C6 119.90(14) . . ?
C4 C5 C8 131.17(13) . . ?
C6 C5 C8 108.92(13) . . ?
C1 C6 C5 121.74(16) . . ?
C1 C6 N2 128.67(15) . . ?
C5 C6 N2 109.59(12) . . ?
O3 C7 N2 126.41(14) . . ?
O3 C7 C8 126.01(12) . . ?
N2 C7 C8 107.58(12) . . ?
C5 C8 C9 117.07(11) . . ?
C5 C8 C7 101.62(11) . . ?
C9 C8 C7 111.19(12) . . ?
C5 C8 C11 114.83(12) . . ?
C9 C8 C11 99.18(10) . . ?
C7 C8 C11 113.53(11) . . ?
C10 C9 C15 127.67(13) . . ?
C10 C9 C8 110.13(12) . . ?
C15 C9 C8 122.04(12) . . ?
N3 C10 O4 114.17(12) . . ?
N3 C10 C9 132.70(14) . . ?
O4 C10 C9 113.12(12) . . ?
O4 C11 C12 108.20(12) . . ?
O4 C11 C8 107.94(10) . . ?
C12 C11 C8 114.68(12) . . ?
O4 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C8 C11 H11A 108.6 . . ?
O1 C12 O2 126.94(14) . . ?
O1 C12 C11 124.97(13) . . ?
O2 C12 C11 108.09(13) . . ?
C14 C13 O2 109.29(16) . . ?
C14 C13 H13A 109.8 . . ?
O2 C13 H13A 109.8 . . ?
C14 C13 H13B 109.8 . . ?
O2 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C9 175.39(17) . . ?

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
C6 C1 C2 C3 0.6(3) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 1.3(2) . . . . ?
C3 C4 C5 C8 -179.85(15) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C2 C1 C6 N2 -178.54(16) . . . . ?
C4 C5 C6 C1 -1.7(2) . . . . ?
C8 C5 C6 C1 179.15(14) . . . . ?
C4 C5 C6 N2 177.68(13) . . . . ?
C8 C5 C6 N2 -1.42(16) . . . . ?
C7 N2 C6 C1 176.78(16) . . . . ?
C7 N2 C6 C5 -2.59(17) . . . . ?
C6 N2 C7 O3 -174.89(14) . . . . ?
C6 N2 C7 C8 5.31(16) . . . . ?
C4 C5 C8 C9 64.0(2) . . . . ?
C6 C5 C8 C9 -117.08(14) . . . . ?
C4 C5 C8 C7 -174.74(15) . . . . ?
C6 C5 C8 C7 4.22(14) . . . . ?
C4 C5 C8 C11 -51.8(2) . . . . ?
C6 C5 C8 C11 127.20(13) . . . . ?
O3 C7 C8 C5 174.51(14) . . . . ?
N2 C7 C8 C5 -5.69(14) . . . . ?
O3 C7 C8 C9 -60.17(18) . . . . ?
N2 C7 C8 C9 119.62(13) . . . . ?
O3 C7 C8 C11 50.65(19) . . . . ?
N2 C7 C8 C11 -129.55(12) . . . . ?
C5 C8 C9 C10 -133.71(14) . . . . ?
C7 C8 C9 C10 110.14(14) . . . . ?
C11 C8 C9 C10 -9.63(16) . . . . ?
C5 C8 C9 C15 50.5(2) . . . . ?
C7 C8 C9 C15 -65.61(18) . . . . ?
C11 C8 C9 C15 174.62(15) . . . . ?
C11 O4 C10 N3 -175.08(14) . . . . ?
C11 O4 C10 C9 3.89(18) . . . . ?
C15 C9 C10 N3 -1.5(3) . . . . ?
C8 C9 C10 N3 -176.99(17) . . . . ?
C15 C9 C10 O4 179.74(15) . . . . ?
C8 C9 C10 O4 4.29(18) . . . . ?
C10 O4 C11 C12 -134.84(13) . . . . ?
C10 O4 C11 C8 -10.20(16) . . . . ?
C5 C8 C11 O4 137.29(12) . . . . ?
C9 C8 C11 O4 11.65(15) . . . . ?
C7 C8 C11 O4 -106.38(13) . . . . ?
C5 C8 C11 C12 -102.04(15) . . . . ?
C9 C8 C11 C12 132.32(13) . . . . ?
C7 C8 C11 C12 14.30(17) . . . . ?
C13 O2 C12 O1 3.0(3) . . . . ?
C13 O2 C12 C11 -177.42(15) . . . . ?
O4 C11 C12 O1 -1.1(2) . . . . ?
C8 C11 C12 O1 -121.62(17) . . . . ?
O4 C11 C12 O2 179.28(12) . . . . ?
C8 C11 C12 O2 58.75(17) . . . . ?
C12 O2 C13 C14 137.98(19) . . . . ?
C10 C9 C15 N1 175(2) . . . . ?
C8 C9 C15 N1 -10(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.031


# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.250 0.060 138 30 ' '
2 0.750 0.750 -0.060 138 30 ' '
_platon_squeeze_details          
;
;
