# Supplementary Information (SI) for Energy & Environmental Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_exp_9154
_audit_block_doi                 10.5517/ccdc.csd.cc2k6bmr
_database_code_depnum_ccdc_archive 'CCDC 2359584'
loop_
_audit_author_name
_audit_author_address
'XiHui Li'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2024-05-31 deposited with the CCDC.	2026-02-10 downloaded from the CCDC.
;
_audit_creation_method           
;
Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)

;
_audit_creation_date             2024-05-15
_chemical_formula_sum            'C12 H14 O6'
_chemical_formula_weight         254.230
_refine_ls_R_factor_all          0.058
_cell_length_a                   5.6643(5)
_cell_length_b                   7.5093(6)
_cell_length_c                   26.967(2)
_cell_angle_alpha                90.000
_cell_angle_beta                 90.000
_cell_angle_gamma                90.000
_cell_volume                     1147.0(2)
_cell_formula_units_Z            4
_symmetry_cell_setting           orthorhombic
_symmetry_int_tables_number      19
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  P_2ac_2ab

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
O ? ?
H ? ?
C ? ?


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
O5 O -0.5441(3) -0.8830(2) -0.0901(0) 1.000 4 a ? d Uani 0.0213(4)
O1 O -0.1307(3) -1.1344(2) 0.2400(1) 1.000 4 a ? d Uani 0.0257(5)
H1 H -0.0556 -1.1247 0.2133 1.000 4 a ? calc Uiso 0.03900
O3 O -0.8380(4) -1.1281(2) 0.1507(1) 1.000 4 a ? d Uani 0.0293(5)
O2 O -0.4587(3) -1.2089(2) 0.1625(0) 1.000 4 a ? d Uani 0.0204(4)
O4 O -0.1708(4) -0.9766(2) -0.0797(1) 1.000 4 a ? d Uani 0.0259(5)
C9 C -0.3432(5) -1.1435(3) 0.0653(1) 1.000 4 a ? d Uani 0.0192(6)
H9 H -0.2346 -1.2080 0.0852 1.000 4 a ? calc Uiso 0.02300
C6 C -0.4414(5) -0.9992(3) -0.0120(1) 1.000 4 a ? d Uani 0.0170(6)
C10 C -0.3669(5) -0.9533(3) -0.0639(1) 1.000 4 a ? d Uani 0.0182(6)
C7 C -0.6606(5) -0.9510(3) 0.0067(1) 1.000 4 a ? d Uani 0.0188(6)
H7 H -0.7688 -0.8861 -0.0132 1.000 4 a ? calc Uiso 0.02300
C3 C -0.6363(5) -1.1455(3) 0.1357(1) 1.000 4 a ? d Uani 0.0186(6)
C8 C -0.7203(5) -0.9989(3) 0.0551(1) 1.000 4 a ? d Uani 0.0190(6)
H8 H -0.8691 -0.9650 0.0684 1.000 4 a ? calc Uiso 0.02300
O6 O -0.9064(4) -0.8450(3) -0.1647(1) 1.000 4 a ? d Uani 0.0329(5)
H6 H -0.9475 -0.8801 -0.1364 1.000 4 a ? calc Uiso 0.04900
C4 C -0.5630(5) -1.0959(3) 0.0842(1) 1.000 4 a ? d Uani 0.0171(6)
C5 C -0.2831(5) -1.0960(3) 0.0169(1) 1.000 4 a ? d Uani 0.0182(6)
H5 H -0.1343 -1.1298 0.0036 1.000 4 a ? calc Uiso 0.02200
C1 C -0.2751(5) -1.2892(3) 0.2383(1) 1.000 4 a ? d Uani 0.0213(6)
H1A H -0.3018 -1.3329 0.2725 1.000 4 a ? calc Uiso 0.02600
H1B H -0.1916 -1.3838 0.2197 1.000 4 a ? calc Uiso 0.02600
C11 C -0.4912(5) -0.8359(3) -0.1417(1) 1.000 4 a ? d Uani 0.0211(6)
H11A H -0.4629 -0.9445 -0.1616 1.000 4 a ? calc Uiso 0.02500
H11B H -0.3489 -0.7596 -0.1434 1.000 4 a ? calc Uiso 0.02500
C2 C -0.5091(5) -1.2541(3) 0.2141(1) 1.000 4 a ? d Uani 0.0196(6)
H2A H -0.6108 -1.3611 0.2159 1.000 4 a ? calc Uiso 0.02300
H2B H -0.5911 -1.1543 0.2308 1.000 4 a ? calc Uiso 0.02300
C12 C -0.7025(5) -0.7378(3) -0.1606(1) 1.000 4 a ? d Uani 0.0233(6)
H12A H -0.7368 -0.6373 -0.1379 1.000 4 a ? calc Uiso 0.02800
H12B H -0.6649 -0.6872 -0.1935 1.000 4 a ? calc Uiso 0.02800


loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O5 0.0196(10) 0.0315(9) 0.0129(8) 0.0018(9) 0.0014(8) 0.0046(7)
O1 0.0280(12) 0.0314(9) 0.0177(8) -0.0058(10) 0.0028(9) -0.0001(8)
O3 0.0208(11) 0.0443(11) 0.0227(9) 0.0045(11) 0.0027(9) 0.0072(8)
O2 0.0194(10) 0.0303(9) 0.0114(7) 0.0015(9) -0.0002(9) 0.0020(7)
O4 0.0214(12) 0.0347(10) 0.0216(9) 0.0059(9) 0.0039(9) 0.0070(8)
C9 0.0184(15) 0.0211(12) 0.0181(12) 0.0027(13) -0.0030(12) 0.0011(11)
C6 0.0184(15) 0.0157(12) 0.0170(11) -0.0057(12) -0.0017(12) -0.0008(10)
C10 0.0199(17) 0.0159(13) 0.0188(13) 0.0006(13) -0.0009(12) -0.0002(11)
C7 0.0174(15) 0.0217(12) 0.0172(12) 0.0009(13) -0.0030(12) 0.0038(11)
C3 0.0177(15) 0.0200(12) 0.0183(12) -0.0020(13) -0.0028(12) -0.0017(11)
C8 0.0167(16) 0.0212(12) 0.0191(12) 0.0004(12) 0.0001(12) -0.0037(11)
O6 0.0250(12) 0.0505(12) 0.0232(9) -0.0077(11) -0.0014(10) 0.0082(9)
C4 0.0208(15) 0.0177(12) 0.0129(11) -0.0030(12) -0.0033(12) -0.0011(10)
C5 0.0137(14) 0.0224(11) 0.0185(12) 0.0005(12) 0.0008(12) -0.0013(11)
C1 0.0253(17) 0.0237(12) 0.0149(12) 0.0008(12) -0.0007(13) 0.0039(11)
C11 0.0224(16) 0.0310(13) 0.0099(11) -0.0020(14) 0.0028(12) 0.0027(11)
C2 0.0201(16) 0.0246(13) 0.0140(11) 0.0026(13) 0.0037(13) 0.0019(11)
C12 0.0219(16) 0.0279(13) 0.0202(13) -0.0011(13) -0.0002(13) 0.0052(11)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O5 C10 . . 1.337(3) no
O5 C11 . . 1.466(2) no
O1 H1 . . 0.8400 no
O1 C1 . . 1.423(3) no
O3 C3 . . 1.219(3) no
O2 C3 . . 1.326(3) no
O2 C2 . . 1.461(2) no
O4 C10 . . 1.203(3) no
C9 H9 . . 0.9500 no
C9 C4 . . 1.392(4) no
C9 C5 . . 1.395(3) no
C6 C10 . . 1.502(3) no
C6 C7 . . 1.388(4) no
C6 C5 . . 1.392(3) no
C7 H7 . . 0.9500 no
C7 C8 . . 1.396(3) no
C3 C4 . . 1.499(3) no
C8 H8 . . 0.9500 no
C8 C4 . . 1.392(3) no
O6 H6 . . 0.8400 no
O6 C12 . . 1.413(3) no
C5 H5 . . 0.9500 no
C1 H1A . . 0.9900 no
C1 H1B . . 0.9900 no
C1 C2 . . 1.501(4) no
C11 H11A . . 0.9900 no
C11 H11B . . 0.9900 no
C11 C12 . . 1.495(4) no
C2 H2A . . 0.9900 no
C2 H2B . . 0.9900 no
C12 H12A . . 0.9900 no
C12 H12B . . 0.9900 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 O5 C11 . . . 116.3(2) no
C1 O1 H1 . . . 109.50 no
C3 O2 C2 . . . 116.9(2) no
C4 C9 H9 . . . 120.20 no
C4 C9 C5 . . . 119.7(2) no
C5 C9 H9 . . . 120.20 no
C7 C6 C10 . . . 122.0(2) no
C7 C6 C5 . . . 120.7(2) no
C5 C6 C10 . . . 117.3(2) no
O5 C10 C6 . . . 111.8(2) no
O4 C10 O5 . . . 124.3(2) no
O4 C10 C6 . . . 123.8(2) no
C6 C7 H7 . . . 120.40 no
C6 C7 C8 . . . 119.3(2) no
C8 C7 H7 . . . 120.40 no
O3 C3 O2 . . . 124.8(2) no
O3 C3 C4 . . . 122.7(2) no
O2 C3 C4 . . . 112.6(2) no
C7 C8 H8 . . . 119.80 no
C4 C8 C7 . . . 120.4(3) no
C4 C8 H8 . . . 119.80 no
C12 O6 H6 . . . 109.50 no
C9 C4 C3 . . . 121.6(2) no
C9 C4 C8 . . . 120.1(2) no
C8 C4 C3 . . . 118.3(2) no
C9 C5 H5 . . . 120.00 no
C6 C5 C9 . . . 119.9(2) no
C6 C5 H5 . . . 120.00 no
O1 C1 H1A . . . 109.20 no
O1 C1 H1B . . . 109.20 no
O1 C1 C2 . . . 112.26(19) no
H1A C1 H1B . . . 107.90 no
C2 C1 H1A . . . 109.20 no
C2 C1 H1B . . . 109.20 no
O5 C11 H11A . . . 110.50 no
O5 C11 H11B . . . 110.50 no
O5 C11 C12 . . . 106.2(2) no
H11A C11 H11B . . . 108.70 no
C12 C11 H11A . . . 110.50 no
C12 C11 H11B . . . 110.50 no
O2 C2 C1 . . . 106.4(2) no
O2 C2 H2A . . . 110.40 no
O2 C2 H2B . . . 110.40 no
C1 C2 H2A . . . 110.40 no
C1 C2 H2B . . . 110.40 no
H2A C2 H2B . . . 108.60 no
O6 C12 C11 . . . 113.63(18) no
O6 C12 H12A . . . 108.80 no
O6 C12 H12B . . . 108.80 no
C11 C12 H12A . . . 108.80 no
C11 C12 H12B . . . 108.80 no
H12A C12 H12B . . . 107.70 no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O5 C11 C12 O6 . . . . -67.2(3) no
O1 C1 C2 O2 . . . . 64.8(2) no
O3 C3 C4 C9 . . . . -169.3(2) no
O3 C3 C4 C8 . . . . 11.2(4) no
O2 C3 C4 C9 . . . . 10.8(3) no
O2 C3 C4 C8 . . . . -168.7(2) no
C6 C7 C8 C4 . . . . -0.8(3) no
C10 O5 C11 C12 . . . . -172.2(2) no
C10 C6 C7 C8 . . . . 179.5(2) no
C10 C6 C5 C9 . . . . -179.6(2) no
C7 C6 C10 O5 . . . . -7.5(3) no
C7 C6 C10 O4 . . . . 172.2(2) no
C7 C6 C5 C9 . . . . -0.8(3) no
C7 C8 C4 C9 . . . . 1.0(3) no
C7 C8 C4 C3 . . . . -179.5(2) no
C3 O2 C2 C1 . . . . -169.74(19) no
C4 C9 C5 C6 . . . . 1.0(3) no
C5 C9 C4 C3 . . . . 179.4(2) no
C5 C9 C4 C8 . . . . -1.1(3) no
C5 C6 C10 O5 . . . . 171.2(2) no
C5 C6 C10 O4 . . . . -9.1(4) no
C5 C6 C7 C8 . . . . 0.8(3) no
C11 O5 C10 O4 . . . . 1.2(4) no
C11 O5 C10 C6 . . . . -179.04(19) no
C2 O2 C3 O3 . . . . -2.5(3) no
C2 O2 C3 C4 . . . . 177.41(18) no
####################################################################### 
# 
# 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_exp_9015
_audit_block_doi                 10.5517/ccdc.csd.cc2k6blq
_database_code_depnum_ccdc_archive 'CCDC 2359583'
loop_
_audit_author_name
_audit_author_address
'xiaoxin Xie'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2024-09-24 deposited with the CCDC.	2026-02-10 downloaded from the CCDC.
;
_audit_creation_date             2024-03-20
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C6 H8 N O2)'
_chemical_formula_sum            'C12 H16 N2 O4'
_chemical_formula_weight         252.27
_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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   4.9229(7)
_cell_length_b                   13.6267(9)
_cell_length_c                   8.8349(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.908(11)
_cell_angle_gamma                90.00
_cell_volume                     587.03(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    690
_cell_measurement_temperature    120.40(10)
_cell_measurement_theta_max      26.8940
_cell_measurement_theta_min      4.6400
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2274
_diffrn_reflns_theta_full        25.98
_diffrn_reflns_theta_max         25.98
_diffrn_reflns_theta_min         2.99
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.40(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.8328
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   64.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852 -178.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852  -37.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00   75.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0852    0.0000    0.0000 127
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0145225000
_diffrn_orient_matrix_UB_12      -0.0433928000
_diffrn_orient_matrix_UB_13      0.0447456000
_diffrn_orient_matrix_UB_21      -0.1238529000
_diffrn_orient_matrix_UB_22      -0.0184232000
_diffrn_orient_matrix_UB_23      -0.0405208000
_diffrn_orient_matrix_UB_31      0.0746921000
_diffrn_orient_matrix_UB_32      -0.0220875000
_diffrn_orient_matrix_UB_33      -0.0541705000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                924
_reflns_number_total             1122
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.07
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.038(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     84
_refine_ls_number_reflns         1122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0418P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0975
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O2 O 0.4945(2) 0.40451(8) 0.10382(12) 0.0250(3) Uani 1 1 d . . .
H2 H 0.5811 0.3538 0.1355 0.037 Uiso 1 1 calc R . .
N1 N 0.5461(3) 0.39786(9) -0.22910(14) 0.0199(4) Uani 1 1 d . . .
H1 H 0.5380 0.4613 -0.2117 0.024 Uiso 1 1 calc R . .
O1 O 0.7322(2) 0.27537(8) -0.35130(12) 0.0257(3) Uani 1 1 d . . .
C2 C 0.8540(3) 0.43703(12) -0.41487(16) 0.0182(4) Uani 1 1 d . . .
C5 C 0.3855(3) 0.33001(12) -0.14843(16) 0.0209(4) Uani 1 1 d . . .
H5A H 0.5013 0.2732 -0.1114 0.025 Uiso 1 1 calc R . .
H5B H 0.2284 0.3052 -0.2203 0.025 Uiso 1 1 calc R . .
C4 C 0.7045(3) 0.36452(12) -0.32863(16) 0.0189(4) Uani 1 1 d . . .
C6 C 0.2801(3) 0.37880(12) -0.01478(18) 0.0244(4) Uani 1 1 d . . .
H6A H 0.1776 0.4388 -0.0509 0.029 Uiso 1 1 calc R . .
H6B H 0.1509 0.3338 0.0270 0.029 Uiso 1 1 calc R . .
C3 C 0.9650(3) 0.40274(12) -0.54171(17) 0.0228(4) Uani 1 1 d . . .
H3 H 0.9414 0.3358 -0.5709 0.027 Uiso 1 1 calc R . .
C1 C 0.8910(3) 0.53519(12) -0.37421(17) 0.0228(4) Uani 1 1 d . . .
H1A H 0.8168 0.5598 -0.2880 0.027 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0346(7) 0.0175(6) 0.0229(6) 0.0003(5) 0.0046(5) 0.0051(5)
N1 0.0260(8) 0.0136(7) 0.0213(7) 0.0002(5) 0.0073(6) -0.0010(6)
O1 0.0326(7) 0.0169(7) 0.0293(6) -0.0032(5) 0.0102(5) -0.0039(5)
C2 0.0174(8) 0.0181(9) 0.0190(8) 0.0004(7) 0.0026(7) 0.0005(7)
C5 0.0234(8) 0.0184(9) 0.0216(8) 0.0010(6) 0.0054(7) -0.0035(7)
C4 0.0194(8) 0.0184(9) 0.0183(8) -0.0010(7) 0.0009(7) -0.0009(7)
C6 0.0247(9) 0.0237(9) 0.0262(9) 0.0033(7) 0.0082(7) 0.0007(8)
C3 0.0280(9) 0.0175(9) 0.0235(8) -0.0040(7) 0.0062(7) -0.0035(7)
C1 0.0273(9) 0.0217(9) 0.0208(8) -0.0026(7) 0.0083(7) -0.0008(8)

_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
O2 H2 0.8400 . ?
O2 C6 1.4251(19) . ?
N1 H1 0.8800 . ?
N1 C5 1.4639(19) . ?
N1 C4 1.3328(19) . ?
O1 C4 1.2417(19) . ?
C2 C4 1.501(2) . ?
C2 C3 1.393(2) . ?
C2 C1 1.390(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.508(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C3 H3 0.9500 . ?
C3 C1 1.384(2) 3_764 ?
C1 C3 1.384(2) 3_764 ?
C1 H1A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O2 H2 109.5 . . ?
C5 N1 H1 119.7 . . ?
C4 N1 H1 119.7 . . ?
C4 N1 C5 120.67(13) . . ?
C3 C2 C4 117.48(15) . . ?
C1 C2 C4 123.91(14) . . ?
C1 C2 C3 118.60(14) . . ?
N1 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
N1 C5 C6 111.71(13) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
N1 C4 C2 118.87(14) . . ?
O1 C4 N1 121.80(13) . . ?
O1 C4 C2 119.33(13) . . ?
O2 C6 C5 112.59(13) . . ?
O2 C6 H6A 109.1 . . ?
O2 C6 H6B 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C2 C3 H3 119.6 . . ?
C1 C3 C2 120.88(15) 3_764 . ?
C1 C3 H3 119.6 3_764 . ?
C2 C1 H1A 119.7 . . ?
C3 C1 C2 120.51(14) 3_764 . ?
C3 C1 H1A 119.7 3_764 . ?

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
N1 C5 C6 O2 -67.05(17) . . . . ?
C5 N1 C4 O1 -3.5(2) . . . . ?
C5 N1 C4 C2 176.81(13) . . . . ?
C4 N1 C5 C6 165.54(14) . . . . ?
C4 C2 C3 C1 -179.09(14) . . . 3_764 ?
C4 C2 C1 C3 179.03(14) . . . 3_764 ?
C3 C2 C4 N1 -165.43(14) . . . . ?
C3 C2 C4 O1 14.8(2) . . . . ?
C3 C2 C1 C3 0.0(3) . . . 3_764 ?
C1 C2 C4 N1 15.5(2) . . . . ?
C1 C2 C4 O1 -164.19(15) . . . . ?
C1 C2 C3 C1 0.0(3) . . . 3_764 ?
