# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_STC21a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            '1:1 pico:sal'
_chemical_source_common          EE/isohexane
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 N2 O4'
_chemical_formula_weight         260.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   13.595(5)
_cell_length_b                   3.710(2)
_cell_length_c                   24.063(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.080(18)
_cell_angle_gamma                90.00
_cell_volume                     1194.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3723
_cell_measurement_theta_min      3.73
_cell_measurement_theta_max      68.03

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_absorpt_coefficient_mu    0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8379
_exptl_absorpt_correction_T_max  0.9730
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'

_exptl_special_details           
; 
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7408
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         66.58
_reflns_number_total             2031
_reflns_number_gt                1819
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.632 (Bruker AXS, 2003)'
_computing_cell_refinement       'Saint V7.36A (Bruker AXS, 2006)'
_computing_data_reduction        'Saint V7.36A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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)+(0.0764P)²+0.2456P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.049(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2031
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0573
_refine_ls_wR_factor_ref         0.1265
_refine_ls_wR_factor_gt          0.1221
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_restrained_S_all      1.201
_refine_ls_shift/su_max          0.009
_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
N1 N 0.03991(9) 0.0504(4) 0.08481(5) 0.0194(3) Uani 1 1 d . . .
C2 C -0.00316(11) -0.0628(4) 0.12756(6) 0.0209(4) Uani 1 1 d . . .
H2 H -0.0689 -0.1584 0.1191 0.025 Uiso 1 1 calc R . .
C3 C 0.04333(12) -0.0479(4) 0.18363(6) 0.0227(4) Uani 1 1 d . . .
H3 H 0.0095 -0.1285 0.2127 0.027 Uiso 1 1 calc R . .
C4 C 0.13958(13) 0.0859(5) 0.19661(6) 0.0248(4) Uani 1 1 d . . .
H4 H 0.1735 0.0955 0.2346 0.030 Uiso 1 1 calc R . .
C5 C 0.18536(11) 0.2056(4) 0.15293(6) 0.0213(4) Uani 1 1 d . . .
H5 H 0.2514 0.2992 0.1603 0.026 Uiso 1 1 calc R . .
C6 C 0.13261(11) 0.1859(4) 0.09811(6) 0.0175(4) Uani 1 1 d . . .
C7 C 0.17884(11) 0.3294(4) 0.05030(6) 0.0186(4) Uani 1 1 d . . .
O8 O 0.26279(8) 0.4724(3) 0.06043(4) 0.0240(3) Uani 1 1 d . . .
N9 N 0.12574(10) 0.3034(4) -0.00097(5) 0.0256(4) Uani 1 1 d . . .
H9A H 0.1495 0.3897 -0.0300 0.031 Uiso 1 1 calc R . .
H9B H 0.0666 0.1998 -0.0061 0.031 Uiso 1 1 calc R . .
O11 O 0.23246(8) 0.8830(3) -0.18264(4) 0.0260(3) Uani 1 1 d . . .
H11 H 0.2069 0.7796 -0.1575 0.039 Uiso 1 1 calc R . .
C12 C 0.33108(11) 0.9416(4) -0.16325(6) 0.0193(4) Uani 1 1 d . . .
C13 C 0.38837(12) 1.0861(4) -0.20034(6) 0.0220(4) Uani 1 1 d . . .
H13 H 0.3582 1.1431 -0.2380 0.026 Uiso 1 1 calc R . .
C14 C 0.48932(12) 1.1468(4) -0.18247(6) 0.0222(4) Uani 1 1 d . . .
H14 H 0.5280 1.2448 -0.2081 0.027 Uiso 1 1 calc R . .
C15 C 0.53512(12) 1.0670(4) -0.12767(7) 0.0228(4) Uani 1 1 d . . .
H15 H 0.6046 1.1088 -0.1159 0.027 Uiso 1 1 calc R . .
C16 C 0.47890(11) 0.9265(4) -0.09042(6) 0.0206(4) Uani 1 1 d . . .
H16 H 0.5099 0.8721 -0.0528 0.025 Uiso 1 1 calc R . .
C17 C 0.37656(11) 0.8633(4) -0.10742(6) 0.0175(4) Uani 1 1 d . . .
C18 C 0.31628(11) 0.7147(4) -0.06759(6) 0.0186(4) Uani 1 1 d . . .
O19 O 0.22691(8) 0.6318(3) -0.08275(4) 0.0237(3) Uani 1 1 d . . .
O20 O 0.36301(8) 0.6807(3) -0.01552(4) 0.0253(3) Uani 1 1 d . . .
H20 H 0.3227 0.6092 0.0049 0.038 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
N1 0.0195(7) 0.0204(7) 0.0182(6) -0.0007(5) 0.0036(5) -0.0013(5)
C2 0.0213(8) 0.0190(9) 0.0233(8) -0.0004(6) 0.0068(6) -0.0030(6)
C3 0.0296(9) 0.0200(9) 0.0200(8) 0.0007(6) 0.0090(6) -0.0004(6)
C4 0.0317(9) 0.0248(9) 0.0170(7) 0.0006(6) 0.0020(6) -0.0013(7)
C5 0.0213(8) 0.0207(9) 0.0208(8) -0.0008(6) 0.0008(6) -0.0020(6)
C6 0.0190(8) 0.0145(8) 0.0192(8) -0.0008(5) 0.0042(6) 0.0010(6)
C7 0.0193(8) 0.0169(9) 0.0196(8) -0.0011(6) 0.0032(6) -0.0009(6)
O8 0.0202(6) 0.0321(7) 0.0192(6) 0.0007(4) 0.0024(4) -0.0083(5)
N9 0.0225(7) 0.0366(9) 0.0172(7) 0.0029(5) 0.0020(5) -0.0117(6)
O11 0.0198(6) 0.0383(8) 0.0192(6) 0.0031(5) 0.0010(4) -0.0030(5)
C12 0.0208(8) 0.0180(8) 0.0188(7) -0.0027(6) 0.0028(6) 0.0019(6)
C13 0.0269(8) 0.0212(9) 0.0183(7) 0.0011(6) 0.0050(6) 0.0031(6)
C14 0.0273(8) 0.0183(8) 0.0236(8) -0.0001(6) 0.0121(6) -0.0011(6)
C15 0.0208(8) 0.0228(9) 0.0257(8) -0.0034(6) 0.0061(6) -0.0034(6)
C16 0.0226(8) 0.0200(9) 0.0190(7) -0.0016(6) 0.0029(6) -0.0010(6)
C17 0.0189(8) 0.0159(8) 0.0177(7) -0.0020(5) 0.0032(6) 0.0001(6)
C18 0.0197(8) 0.0168(8) 0.0190(7) -0.0011(6) 0.0025(6) -0.0005(6)
O19 0.0187(6) 0.0323(7) 0.0199(6) 0.0012(4) 0.0028(4) -0.0047(5)
O20 0.0222(6) 0.0371(8) 0.0163(6) 0.0031(5) 0.0025(4) -0.0076(5)

_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
N1 C2 1.337(2) . ?
N1 C6 1.342(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.502(2) . ?
C7 O8 1.2434(19) . ?
C7 N9 1.319(2) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
O11 C12 1.3577(19) . ?
O11 H11 0.8400 . ?
C12 C13 1.391(2) . ?
C12 C17 1.407(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.378(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.400(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.473(2) . ?
C18 O19 1.2444(19) . ?
C18 O20 1.3080(18) . ?
O20 H20 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 116.96(13) . . ?
N1 C2 C3 123.32(14) . . ?
N1 C2 H2 118.3 . . ?
C3 C2 H2 118.3 . . ?
C4 C3 C2 119.07(14) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 118.47(14) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 118.55(14) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
N1 C6 C5 123.60(13) . . ?
N1 C6 C7 116.83(13) . . ?
C5 C6 C7 119.55(13) . . ?
O8 C7 N9 123.21(13) . . ?
O8 C7 C6 119.60(13) . . ?
N9 C7 C6 117.17(13) . . ?
C7 N9 H9A 120.0 . . ?
C7 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C12 O11 H11 109.5 . . ?
O11 C12 C13 118.13(13) . . ?
O11 C12 C17 122.51(13) . . ?
C13 C12 C17 119.36(14) . . ?
C14 C13 C12 120.01(14) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.09(14) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 119.40(15) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 120.62(14) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C12 119.52(14) . . ?
C16 C17 C18 120.69(13) . . ?
C12 C17 C18 119.79(13) . . ?
O19 C18 O20 122.86(13) . . ?
O19 C18 C17 121.84(13) . . ?
O20 C18 C17 115.29(13) . . ?
C18 O20 H20 109.5 . . ?

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 N1 C2 C3 -0.4(2) . . . . ?
N1 C2 C3 C4 -0.9(2) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C2 N1 C6 C5 1.5(2) . . . . ?
C2 N1 C6 C7 -177.11(14) . . . . ?
C4 C5 C6 N1 -1.3(2) . . . . ?
C4 C5 C6 C7 177.25(15) . . . . ?
N1 C6 C7 O8 176.88(14) . . . . ?
C5 C6 C7 O8 -1.8(2) . . . . ?
N1 C6 C7 N9 -1.5(2) . . . . ?
C5 C6 C7 N9 179.84(14) . . . . ?
O11 C12 C13 C14 -179.38(14) . . . . ?
C17 C12 C13 C14 0.9(2) . . . . ?
C12 C13 C14 C15 -0.2(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 C12 0.5(2) . . . . ?
C15 C16 C17 C18 -179.74(14) . . . . ?
O11 C12 C17 C16 179.26(14) . . . . ?
C13 C12 C17 C16 -1.0(2) . . . . ?
O11 C12 C17 C18 -0.5(2) . . . . ?
C13 C12 C17 C18 179.20(14) . . . . ?
C16 C17 C18 O19 -174.72(15) . . . . ?
C12 C17 C18 O19 5.0(2) . . . . ?
C16 C17 C18 O20 6.0(2) . . . . ?
C12 C17 C18 O20 -174.20(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9A O19 0.88 2.00 2.8629(18) 167.2 .
N9 H9B N1 0.88 2.36 3.045(2) 134.5 3
O11 H11 O19 0.84 1.86 2.5914(17) 145.4 .
O20 H20 O8 0.84 1.76 2.5817(16) 166.5 .

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         0.476
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.157
_database_code_depnum_ccdc_archive 'CCDC 977784'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_STC22a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            '2:1 pico:succ'
_chemical_source_common          EtOH
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N4 O6'
_chemical_formula_weight         362.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   32.561(10)
_cell_length_b                   5.078(2)
_cell_length_c                   20.831(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.811(13)
_cell_angle_gamma                90.00
_cell_volume                     3314.0(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7099
_cell_measurement_theta_min      4.54
_cell_measurement_theta_max      67.98

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8938
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'

_exptl_special_details           
; 
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16646
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         66.53
_reflns_number_total             2896
_reflns_number_gt                2566
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.632 (Bruker AXS, 2003)'
_computing_cell_refinement       'Saint V7.36A (Bruker AXS, 2006)'
_computing_data_reduction        'Saint V7.36A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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)+(0.0642P)²+3.9088P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0050(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2896
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_restrained_S_all      0.920
_refine_ls_shift/su_max          0.016
_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
N1 N 0.17813(4) -0.0162(2) 1.30778(6) 0.0213(3) Uani 1 1 d . . .
C2 C 0.20422(5) 0.1864(3) 1.30718(7) 0.0228(3) Uani 1 1 d . . .
H2 H 0.2197 0.2600 1.3486 0.027 Uiso 1 1 calc R . .
C3 C 0.20982(4) 0.2944(3) 1.24900(7) 0.0208(3) Uani 1 1 d . . .
H3 H 0.2285 0.4396 1.2508 0.025 Uiso 1 1 calc R . .
C4 C 0.18789(4) 0.1882(3) 1.18844(7) 0.0211(3) Uani 1 1 d . . .
H4 H 0.1913 0.2581 1.1479 0.025 Uiso 1 1 calc R . .
C5 C 0.16066(4) -0.0230(3) 1.18780(7) 0.0200(3) Uani 1 1 d . . .
H5 H 0.1452 -0.1015 1.1470 0.024 Uiso 1 1 calc R . .
C6 C 0.15666(4) -0.1161(3) 1.24837(7) 0.0171(3) Uani 1 1 d . . .
C7 C 0.12640(4) -0.3372(3) 1.25013(7) 0.0171(3) Uani 1 1 d . . .
O8 O 0.10456(3) -0.4368(2) 1.19714(5) 0.0212(3) Uani 1 1 d . . .
N9 N 0.12419(4) -0.4110(3) 1.30991(6) 0.0224(3) Uani 1 1 d . . .
H9A H 0.1065 -0.5373 1.3139 0.027 Uiso 1 1 calc R . .
H9B H 0.1404 -0.3338 1.3458 0.027 Uiso 1 1 calc R . .
C11 C 0.01305(5) -1.1463(3) 1.22469(7) 0.0217(3) Uani 1 1 d . . .
H11A H 0.0290 -1.3139 1.2282 0.026 Uiso 1 1 calc R . .
H11B H -0.0065 -1.1352 1.1791 0.026 Uiso 1 1 calc R . .
C12 C 0.04398(4) -0.9197(3) 1.23550(7) 0.0193(3) Uani 1 1 d . . .
O13 O 0.05812(4) -0.8145(2) 1.28967(5) 0.0286(3) Uani 1 1 d . . .
O14 O 0.05450(3) -0.8467(2) 1.18139(5) 0.0233(3) Uani 1 1 d . . .
H14 H 0.0720 -0.7215 1.1907 0.035 Uiso 1 1 calc R . .
N21 N 0.06409(4) 0.3617(2) 0.92152(6) 0.0198(3) Uani 1 1 d . . .
C22 C 0.03582(5) 0.5533(3) 0.91979(7) 0.0218(3) Uani 1 1 d . . .
H22 H 0.0154 0.5892 0.8785 0.026 Uiso 1 1 calc R . .
C23 C 0.03452(5) 0.7032(3) 0.97489(7) 0.0224(3) Uani 1 1 d . . .
H23 H 0.0139 0.8388 0.9710 0.027 Uiso 1 1 calc R . .
C24 C 0.06380(5) 0.6521(3) 1.03559(7) 0.0221(3) Uani 1 1 d . . .
H24 H 0.0634 0.7496 1.0743 0.027 Uiso 1 1 calc R . .
C25 C 0.09377(4) 0.4542(3) 1.03834(7) 0.0199(3) Uani 1 1 d . . .
H25 H 0.1145 0.4147 1.0790 0.024 Uiso 1 1 calc R . .
C26 C 0.09272(4) 0.3160(3) 0.98064(7) 0.0171(3) Uani 1 1 d . . .
C27 C 0.12466(4) 0.1018(3) 0.98138(7) 0.0169(3) Uani 1 1 d . . .
O28 O 0.15353(3) 0.0590(2) 1.03351(5) 0.0205(3) Uani 1 1 d . . .
N29 N 0.12025(4) -0.0322(2) 0.92546(6) 0.0198(3) Uani 1 1 d . . .
H29A H 0.1383 -0.1594 0.9237 0.024 Uiso 1 1 calc R . .
H29B H 0.0993 0.0058 0.8900 0.024 Uiso 1 1 calc R . .
C31 C 0.24720(4) -0.6687(3) 1.02901(7) 0.0203(3) Uani 1 1 d . . .
H31A H 0.2418 -0.7883 1.0633 0.024 Uiso 1 1 calc R . .
H31B H 0.2740 -0.5722 1.0493 0.024 Uiso 1 1 calc R . .
C32 C 0.21107(4) -0.4740(3) 1.00883(7) 0.0187(3) Uani 1 1 d . . .
O33 O 0.18771(3) -0.4512(2) 0.95256(5) 0.0228(3) Uani 1 1 d . . .
O34 O 0.20775(3) -0.3274(2) 1.05966(5) 0.0245(3) Uani 1 1 d . . .
H34 H 0.1882 -0.2163 1.0463 0.029 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
N1 0.0223(6) 0.0223(7) 0.0189(6) -0.0020(5) 0.0052(5) -0.0024(5)
C2 0.0216(7) 0.0239(8) 0.0215(7) -0.0031(6) 0.0037(6) -0.0026(6)
C3 0.0151(7) 0.0189(7) 0.0282(8) 0.0005(6) 0.0055(6) 0.0006(5)
C4 0.0186(7) 0.0253(8) 0.0201(7) 0.0049(6) 0.0065(6) 0.0024(6)
C5 0.0178(7) 0.0228(8) 0.0179(7) -0.0001(6) 0.0026(5) 0.0016(6)
C6 0.0147(7) 0.0178(7) 0.0187(7) 0.0000(5) 0.0042(5) 0.0032(5)
C7 0.0153(7) 0.0169(7) 0.0190(7) -0.0003(5) 0.0044(6) 0.0046(5)
O8 0.0210(5) 0.0232(6) 0.0179(5) -0.0005(4) 0.0026(4) -0.0025(4)
N9 0.0257(7) 0.0234(7) 0.0180(6) -0.0019(5) 0.0056(5) -0.0076(5)
C11 0.0182(7) 0.0182(8) 0.0265(8) -0.0025(6) 0.0026(6) 0.0019(6)
C12 0.0159(7) 0.0183(7) 0.0221(7) 0.0012(6) 0.0026(6) 0.0045(5)
O13 0.0332(6) 0.0300(6) 0.0216(6) -0.0022(4) 0.0058(5) -0.0126(5)
O14 0.0230(6) 0.0246(6) 0.0222(5) -0.0026(4) 0.0063(4) -0.0040(4)
N21 0.0192(6) 0.0205(6) 0.0183(6) 0.0002(5) 0.0027(5) 0.0013(5)
C22 0.0198(7) 0.0221(8) 0.0213(7) 0.0019(6) 0.0017(6) 0.0030(6)
C23 0.0202(7) 0.0201(8) 0.0277(8) -0.0003(6) 0.0080(6) 0.0027(6)
C24 0.0227(7) 0.0237(8) 0.0213(7) -0.0045(6) 0.0082(6) -0.0011(6)
C25 0.0187(7) 0.0225(8) 0.0180(7) 0.0004(5) 0.0042(6) -0.0008(6)
C26 0.0158(7) 0.0182(7) 0.0175(7) 0.0018(5) 0.0049(5) -0.0011(5)
C27 0.0164(7) 0.0179(7) 0.0162(7) 0.0019(5) 0.0043(5) -0.0020(5)
O28 0.0200(5) 0.0220(6) 0.0171(5) -0.0001(4) 0.0012(4) 0.0030(4)
N29 0.0205(6) 0.0204(6) 0.0170(6) -0.0008(5) 0.0026(5) 0.0044(5)
C31 0.0184(7) 0.0201(8) 0.0220(7) 0.0004(6) 0.0047(6) 0.0017(6)
C32 0.0179(7) 0.0186(7) 0.0201(7) 0.0009(5) 0.0058(6) -0.0019(5)
O33 0.0240(6) 0.0239(6) 0.0195(5) 0.0014(4) 0.0042(4) 0.0054(4)
O34 0.0237(6) 0.0253(6) 0.0218(5) -0.0031(4) 0.0014(4) 0.0090(4)

_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
N1 C2 1.336(2) . ?
N1 C6 1.3439(19) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.501(2) . ?
C7 O8 1.2459(17) . ?
C7 N9 1.3212(19) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
C11 C12 1.505(2) . ?
C11 C11 1.524(3) 2_557 ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 O13 1.2196(18) . ?
C12 O14 1.3174(18) . ?
O14 H14 0.8400 . ?
N21 C22 1.3329(19) . ?
N21 C26 1.3470(18) . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.502(2) . ?
C27 O28 1.2466(17) . ?
C27 N29 1.3226(18) . ?
N29 H29A 0.8800 . ?
N29 H29B 0.8800 . ?
C31 C32 1.506(2) . ?
C31 C31 1.515(3) 7_537 ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 O33 1.2164(17) . ?
C32 O34 1.3226(17) . ?
O34 H34 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 117.01(12) . . ?
N1 C2 C3 123.24(13) . . ?
N1 C2 H2 118.4 . . ?
C3 C2 H2 118.4 . . ?
C4 C3 C2 119.07(14) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 118.75(13) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 118.18(13) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
N1 C6 C5 123.74(13) . . ?
N1 C6 C7 116.10(12) . . ?
C5 C6 C7 120.15(12) . . ?
O8 C7 N9 123.73(13) . . ?
O8 C7 C6 120.15(12) . . ?
N9 C7 C6 116.10(12) . . ?
C7 N9 H9A 120.0 . . ?
C7 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C12 C11 C11 111.91(11) . 2_557 ?
C12 C11 H11A 109.2 . . ?
C11 C11 H11A 109.2 2_557 . ?
C12 C11 H11B 109.2 . . ?
C11 C11 H11B 109.2 2_557 . ?
H11A C11 H11B 107.9 . . ?
O13 C12 O14 123.22(14) . . ?
O13 C12 C11 122.80(13) . . ?
O14 C12 C11 113.98(12) . . ?
C12 O14 H14 109.5 . . ?
C22 N21 C26 116.82(12) . . ?
N21 C22 C23 123.68(13) . . ?
N21 C22 H22 118.2 . . ?
C23 C22 H22 118.2 . . ?
C24 C23 C22 118.93(13) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 118.27(13) . . ?
C23 C24 H24 120.9 . . ?
C25 C24 H24 120.9 . . ?
C26 C25 C24 118.65(13) . . ?
C26 C25 H25 120.7 . . ?
C24 C25 H25 120.7 . . ?
N21 C26 C25 123.63(13) . . ?
N21 C26 C27 116.04(12) . . ?
C25 C26 C27 120.33(12) . . ?
O28 C27 N29 123.56(13) . . ?
O28 C27 C26 119.39(12) . . ?
N29 C27 C26 117.05(12) . . ?
C27 N29 H29A 120.0 . . ?
C27 N29 H29B 120.0 . . ?
H29A N29 H29B 120.0 . . ?
C32 C31 C31 112.94(15) . 7_537 ?
C32 C31 H31A 109.0 . . ?
C31 C31 H31A 109.0 7_537 . ?
C32 C31 H31B 109.0 . . ?
C31 C31 H31B 109.0 7_537 . ?
H31A C31 H31B 107.8 . . ?
O33 C32 O34 123.49(13) . . ?
O33 C32 C31 124.55(13) . . ?
O34 C32 C31 111.96(11) . . ?
C32 O34 H34 109.5 . . ?

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 N1 C2 C3 0.0(2) . . . . ?
N1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C2 N1 C6 C5 0.9(2) . . . . ?
C2 N1 C6 C7 -177.92(12) . . . . ?
C4 C5 C6 N1 -1.1(2) . . . . ?
C4 C5 C6 C7 177.71(12) . . . . ?
N1 C6 C7 O8 178.41(12) . . . . ?
C5 C6 C7 O8 -0.4(2) . . . . ?
N1 C6 C7 N9 -0.24(18) . . . . ?
C5 C6 C7 N9 -179.09(13) . . . . ?
C11 C11 C12 O13 25.9(2) 2_557 . . . ?
C11 C11 C12 O14 -154.38(13) 2_557 . . . ?
C26 N21 C22 C23 -0.3(2) . . . . ?
N21 C22 C23 C24 -0.6(2) . . . . ?
C22 C23 C24 C25 1.0(2) . . . . ?
C23 C24 C25 C26 -0.6(2) . . . . ?
C22 N21 C26 C25 0.6(2) . . . . ?
C22 N21 C26 C27 -179.25(12) . . . . ?
C24 C25 C26 N21 -0.2(2) . . . . ?
C24 C25 C26 C27 179.69(13) . . . . ?
N21 C26 C27 O28 176.05(12) . . . . ?
C25 C26 C27 O28 -3.8(2) . . . . ?
N21 C26 C27 N29 -3.93(18) . . . . ?
C25 C26 C27 N29 176.18(13) . . . . ?
C31 C31 C32 O33 1.9(2) 7_537 . . . ?
C31 C31 C32 O34 -177.61(15) 7_537 . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9A O13 0.88 2.07 2.9172(18) 161.1 .
N9 H9B O33 0.88 2.58 3.2014(18) 128.5 6_546
N9 H9B N29 0.88 2.69 3.3231(19) 129.9 6_556
O14 H14 O8 0.84 1.78 2.6087(16) 170.6 .
N29 H29A O33 0.88 2.15 2.9991(17) 162.1 .
N29 H29B O13 0.88 2.36 3.0955(18) 140.9 6_545
O34 H34 O28 0.84 1.77 2.5959(15) 167.2 .

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        66.53
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.121
_database_code_depnum_ccdc_archive 'CCDC 977785'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_STC23a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            '2:1 pico:fum'
_chemical_source_common          EtOH
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N2 O3'
_chemical_formula_weight         180.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   8.479(3)
_cell_length_b                   4.979(2)
_cell_length_c                   19.167(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.083(18)
_cell_angle_gamma                90.00
_cell_volume                     809.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2729
_cell_measurement_theta_min      4.61
_cell_measurement_theta_max      67.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9257
_exptl_absorpt_correction_T_max  0.9712
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5538
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.61
_diffrn_reflns_theta_max         66.57
_reflns_number_total             1409
_reflns_number_gt                1262
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.632 (Bruker AXS, 2003)'
_computing_cell_refinement       'Saint V7.36A (Bruker AXS, 2006)'
_computing_data_reduction        'Saint V7.36A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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)+(0.0625P)²+0.1694P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.067(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1409
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.1055
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_restrained_S_all      1.200
_refine_ls_shift/su_max          0.007
_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
N1 N 0.89511(14) 0.3176(2) 0.11546(6) 0.0176(3) Uani 1 1 d . . .
C2 C 0.81568(18) 0.1135(3) 0.14390(8) 0.0189(4) Uani 1 1 d . . .
H2 H 0.7220 0.0541 0.1215 0.023 Uiso 1 1 calc R . .
C3 C 0.86313(17) -0.0165(3) 0.20461(7) 0.0186(4) Uani 1 1 d . . .
H3 H 0.8035 -0.1623 0.2226 0.022 Uiso 1 1 calc R . .
C4 C 0.99800(17) 0.0691(3) 0.23840(8) 0.0190(4) Uani 1 1 d . . .
H4 H 1.0317 -0.0139 0.2805 0.023 Uiso 1 1 calc R . .
C5 C 1.08321(17) 0.2797(3) 0.20933(7) 0.0175(4) Uani 1 1 d . . .
H5 H 1.1770 0.3431 0.2309 0.021 Uiso 1 1 calc R . .
C6 C 1.02835(17) 0.3949(3) 0.14818(7) 0.0155(4) Uani 1 1 d . . .
C7 C 1.12003(16) 0.6168(3) 0.11402(7) 0.0156(4) Uani 1 1 d . . .
O8 O 1.25044(11) 0.6847(2) 0.13881(5) 0.0187(3) Uani 1 1 d . . .
N9 N 1.05656(14) 0.7269(2) 0.05788(6) 0.0179(3) Uani 1 1 d . . .
H9A H 1.1067 0.8559 0.0357 0.021 Uiso 1 1 calc R . .
H9B H 0.9642 0.6712 0.0427 0.021 Uiso 1 1 calc R . .
C11 C 1.50656(17) 1.4285(3) 0.02901(8) 0.0178(4) Uani 1 1 d . . .
H11 H 1.5929 1.4608 0.0595 0.021 Uiso 1 1 calc R . .
C12 C 1.38874(17) 1.2181(3) 0.04735(7) 0.0166(4) Uani 1 1 d . . .
O13 O 1.27113(12) 1.1721(2) 0.01268(5) 0.0207(3) Uani 1 1 d . . .
O14 O 1.42737(12) 1.0864(2) 0.10450(5) 0.0206(3) Uani 1 1 d . . .
H14 H 1.3609 0.9647 0.1119 0.031 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
N1 0.0157(7) 0.0195(7) 0.0177(6) -0.0008(5) -0.0012(5) -0.0003(5)
C2 0.0150(7) 0.0204(8) 0.0214(8) -0.0025(6) -0.0004(6) -0.0021(6)
C3 0.0174(8) 0.0172(7) 0.0213(8) -0.0003(6) 0.0045(6) -0.0005(6)
C4 0.0197(8) 0.0204(8) 0.0170(7) 0.0025(6) 0.0007(6) 0.0032(6)
C5 0.0146(8) 0.0203(8) 0.0177(7) -0.0003(5) -0.0022(6) 0.0000(5)
C6 0.0146(7) 0.0152(7) 0.0166(7) -0.0021(5) 0.0008(5) 0.0016(5)
C7 0.0158(8) 0.0156(7) 0.0153(7) -0.0031(5) 0.0006(5) 0.0026(6)
O8 0.0161(6) 0.0204(6) 0.0196(6) 0.0023(4) -0.0029(4) -0.0027(4)
N9 0.0167(7) 0.0197(7) 0.0174(6) 0.0030(5) -0.0026(5) -0.0023(5)
C11 0.0149(8) 0.0191(8) 0.0194(7) -0.0014(6) -0.0011(6) -0.0005(6)
C12 0.0158(8) 0.0169(8) 0.0170(7) -0.0015(5) 0.0006(6) 0.0024(5)
O13 0.0189(6) 0.0222(6) 0.0210(6) 0.0028(4) -0.0040(4) -0.0047(4)
O14 0.0187(6) 0.0212(6) 0.0218(6) 0.0057(4) -0.0030(4) -0.0046(4)

_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
N1 C2 1.336(2) . ?
N1 C6 1.3475(19) . ?
C2 C3 1.390(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.502(2) . ?
C7 O8 1.2494(18) . ?
C7 N9 1.3214(19) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
C11 C11 1.325(3) 3_885 ?
C11 C12 1.490(2) . ?
C11 H11 0.9500 . ?
C12 O13 1.2192(18) . ?
C12 O14 1.3176(18) . ?
O14 H14 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 116.77(13) . . ?
N1 C2 C3 123.37(14) . . ?
N1 C2 H2 118.3 . . ?
C3 C2 H2 118.3 . . ?
C4 C3 C2 119.17(14) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 118.38(13) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 118.52(13) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
N1 C6 C5 123.77(13) . . ?
N1 C6 C7 116.20(13) . . ?
C5 C6 C7 120.02(13) . . ?
O8 C7 N9 123.83(13) . . ?
O8 C7 C6 119.44(13) . . ?
N9 C7 C6 116.72(13) . . ?
C7 N9 H9A 120.0 . . ?
C7 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C11 C11 C12 121.35(17) 3_885 . ?
C11 C11 H11 119.3 3_885 . ?
C12 C11 H11 119.3 . . ?
O13 C12 O14 124.17(13) . . ?
O13 C12 C11 123.48(13) . . ?
O14 C12 C11 112.34(12) . . ?
C12 O14 H14 109.5 . . ?

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 N1 C2 C3 0.7(2) . . . . ?
N1 C2 C3 C4 0.8(2) . . . . ?
C2 C3 C4 C5 -1.3(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C2 N1 C6 C5 -1.6(2) . . . . ?
C2 N1 C6 C7 177.53(12) . . . . ?
C4 C5 C6 N1 1.1(2) . . . . ?
C4 C5 C6 C7 -178.03(13) . . . . ?
N1 C6 C7 O8 -174.78(12) . . . . ?
C5 C6 C7 O8 4.4(2) . . . . ?
N1 C6 C7 N9 4.28(19) . . . . ?
C5 C6 C7 N9 -176.55(13) . . . . ?
C11 C11 C12 O13 -3.3(3) 3_885 . . . ?
C11 C11 C12 O14 175.88(17) 3_885 . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9A O13 0.88 2.15 2.9965(18) 161.4 .
N9 H9B O13 0.88 2.39 3.1291(18) 141.8 3_775
O14 H14 O8 0.84 1.76 2.5859(16) 168.5 .

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        66.57
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.135
_database_code_depnum_ccdc_archive 'CCDC 977786'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_STC24a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;

_chemical_name_common            '2:1 pico:adi'
_chemical_source_common          EtOH
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 N2 O3'
_chemical_formula_weight         195.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   7.546(2)
_cell_length_b                   11.745(3)
_cell_length_c                   10.595(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.210(13)
_cell_angle_gamma                90.00
_cell_volume                     939.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4950
_cell_measurement_theta_min      5.51
_cell_measurement_theta_max      68.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             412
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8571
_exptl_absorpt_correction_T_max  0.9168
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'

_exptl_special_details           
; 
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9175
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.62
_diffrn_reflns_theta_max         66.54
_reflns_number_total             1627
_reflns_number_gt                1492
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.632 (Bruker AXS, 2003)'
_computing_cell_refinement       'Saint V7.36A (Bruker AXS, 2006)'
_computing_data_reduction        'Saint V7.36A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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)+(0.0452P)²+0.2638P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1627
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0824
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.010
_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
N1 N 0.56209(12) 0.14001(8) -0.02165(9) 0.0193(2) Uani 1 1 d . . .
C2 C 0.72440(15) 0.09462(11) -0.01964(11) 0.0224(3) Uani 1 1 d . . .
H2 H 0.7708 0.0650 -0.0961 0.027 Uiso 1 1 calc R . .
C3 C 0.82888(15) 0.08839(10) 0.08826(11) 0.0225(3) Uani 1 1 d . . .
H3 H 0.9427 0.0539 0.0854 0.027 Uiso 1 1 calc R . .
C4 C 0.76532(15) 0.13289(10) 0.19970(11) 0.0205(3) Uani 1 1 d . . .
H4 H 0.8345 0.1303 0.2747 0.025 Uiso 1 1 calc R . .
C5 C 0.59764(15) 0.18150(10) 0.19952(11) 0.0190(3) Uani 1 1 d . . .
H5 H 0.5499 0.2139 0.2742 0.023 Uiso 1 1 calc R . .
C6 C 0.50159(14) 0.18176(9) 0.08806(10) 0.0165(3) Uani 1 1 d . . .
C7 C 0.31896(15) 0.23286(9) 0.08562(11) 0.0176(3) Uani 1 1 d . . .
O8 O 0.25555(10) 0.27509(7) 0.18351(7) 0.0234(2) Uani 1 1 d . . .
N9 N 0.23445(12) 0.23016(9) -0.02424(9) 0.0202(2) Uani 1 1 d . . .
H9A H 0.1274 0.2593 -0.0309 0.024 Uiso 1 1 calc R . .
H9B H 0.2854 0.1993 -0.0905 0.024 Uiso 1 1 calc R . .
C11 C -0.40985(14) 0.47217(10) -0.00888(10) 0.0180(3) Uani 1 1 d . . .
H11A H -0.3438 0.5140 -0.0748 0.022 Uiso 1 1 calc R . .
H11B H -0.4270 0.3930 -0.0387 0.022 Uiso 1 1 calc R . .
C12 C -0.30009(14) 0.47052(10) 0.11231(10) 0.0184(3) Uani 1 1 d . . .
H12A H -0.2746 0.5498 0.1384 0.022 Uiso 1 1 calc R . .
H12B H -0.3699 0.4341 0.1802 0.022 Uiso 1 1 calc R . .
C13 C -0.12846(15) 0.40740(9) 0.09678(10) 0.0174(3) Uani 1 1 d . . .
O14 O -0.07958(10) 0.36663(7) -0.00275(7) 0.0230(2) Uani 1 1 d . . .
O15 O -0.03500(10) 0.39980(7) 0.20297(7) 0.0214(2) Uani 1 1 d . . .
H15 H 0.0554 0.3597 0.1905 0.032 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
N1 0.0181(5) 0.0219(5) 0.0178(5) 0.0003(4) -0.0001(4) 0.0018(4)
C2 0.0209(6) 0.0281(6) 0.0181(6) -0.0019(5) 0.0021(5) 0.0056(5)
C3 0.0161(6) 0.0278(6) 0.0236(6) 0.0010(5) 0.0008(5) 0.0056(5)
C4 0.0189(6) 0.0252(6) 0.0174(6) 0.0028(5) -0.0026(4) 0.0010(4)
C5 0.0201(6) 0.0216(6) 0.0154(6) 0.0016(4) 0.0012(4) 0.0020(4)
C6 0.0164(6) 0.0164(5) 0.0166(6) 0.0025(4) 0.0011(4) -0.0002(4)
C7 0.0173(6) 0.0183(6) 0.0172(6) 0.0027(4) 0.0015(4) 0.0010(4)
O8 0.0206(4) 0.0337(5) 0.0159(4) 0.0005(3) 0.0009(3) 0.0084(3)
N9 0.0155(5) 0.0280(6) 0.0171(5) -0.0010(4) -0.0013(4) 0.0045(4)
C11 0.0173(6) 0.0196(6) 0.0171(6) -0.0001(4) -0.0007(4) 0.0025(4)
C12 0.0170(6) 0.0202(6) 0.0179(6) -0.0008(4) -0.0009(4) 0.0020(4)
C13 0.0177(6) 0.0182(5) 0.0162(6) 0.0013(4) -0.0014(4) -0.0010(4)
O14 0.0212(4) 0.0313(5) 0.0165(4) -0.0024(3) -0.0022(3) 0.0081(3)
O15 0.0161(4) 0.0309(5) 0.0172(4) -0.0019(3) -0.0030(3) 0.0064(3)

_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
N1 C2 1.3359(16) . ?
N1 C6 1.3431(15) . ?
C2 C3 1.3882(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3790(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3881(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3833(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.5033(15) . ?
C7 O8 1.2467(14) . ?
C7 N9 1.3255(15) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
C11 C11 1.522(2) 3_465 ?
C11 C12 1.5255(16) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5018(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O14 1.2166(14) . ?
C13 O15 1.3287(14) . ?
O15 H15 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 116.51(10) . . ?
N1 C2 C3 123.51(11) . . ?
N1 C2 H2 118.2 . . ?
C3 C2 H2 118.2 . . ?
C4 C3 C2 119.14(11) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 118.33(11) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 118.48(10) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N1 C6 C5 124.01(10) . . ?
N1 C6 C7 116.45(10) . . ?
C5 C6 C7 119.54(10) . . ?
O8 C7 N9 123.72(10) . . ?
O8 C7 C6 119.94(10) . . ?
N9 C7 C6 116.33(10) . . ?
C7 N9 H9A 120.0 . . ?
C7 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C11 C11 C12 112.60(11) 3_465 . ?
C11 C11 H11A 109.1 3_465 . ?
C12 C11 H11A 109.1 . . ?
C11 C11 H11B 109.1 3_465 . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 112.32(9) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
O14 C13 O15 123.08(10) . . ?
O14 C13 C12 123.61(10) . . ?
O15 C13 C12 113.31(9) . . ?
C13 O15 H15 109.5 . . ?

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 N1 C2 C3 0.51(17) . . . . ?
N1 C2 C3 C4 -1.27(19) . . . . ?
C2 C3 C4 C5 0.57(18) . . . . ?
C3 C4 C5 C6 0.76(17) . . . . ?
C2 N1 C6 C5 0.95(16) . . . . ?
C2 N1 C6 C7 179.97(10) . . . . ?
C4 C5 C6 N1 -1.59(17) . . . . ?
C4 C5 C6 C7 179.41(10) . . . . ?
N1 C6 C7 O8 -178.72(10) . . . . ?
C5 C6 C7 O8 0.35(16) . . . . ?
N1 C6 C7 N9 0.97(15) . . . . ?
C5 C6 C7 N9 -179.96(10) . . . . ?
C11 C11 C12 C13 175.49(11) 3_465 . . . ?
C11 C12 C13 O14 2.98(16) . . . . ?
C11 C12 C13 O15 -176.68(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9A O14 0.88 2.03 2.8706(13) 159.4 .
N9 H9B O8 0.88 2.42 3.1017(15) 134.2 4_565
O15 H15 O8 0.84 1.81 2.6454(12) 173.2 .

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        66.54
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 977787'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_STC25a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            '1:1 pico:adi'
_chemical_source_common          EtOH
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H16 N2 O5'
_chemical_formula_weight         268.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   7.006(2)
_cell_length_b                   20.510(6)
_cell_length_c                   9.125(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.06(2)
_cell_angle_gamma                90.00
_cell_volume                     1260.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2578
_cell_measurement_theta_min      4.27
_cell_measurement_theta_max      68.22

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8721
_exptl_absorpt_correction_T_max  0.9634
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'

_exptl_special_details           
; 
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9341
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0324
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.31
_diffrn_reflns_theta_max         66.58
_reflns_number_total             2213
_reflns_number_gt                1894
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.632 (Bruker AXS, 2003)'
_computing_cell_refinement       'Saint V7.36A (Bruker AXS, 2006)'
_computing_data_reduction        'Saint V7.36A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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)+(0.1309P)²+3.3520P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2213
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.1083
_refine_ls_wR_factor_gt          0.0946
_refine_ls_goodness_of_fit_ref   0.498
_refine_ls_restrained_S_all      0.498
_refine_ls_shift/su_max          0.008
_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
N1 N 1.10590(19) -0.29575(6) -0.12737(14) 0.0157(3) Uani 1 1 d . . .
C2 C 1.2227(2) -0.33353(8) -0.18579(17) 0.0175(3) Uani 1 1 d . . .
H2 H 1.2082 -0.3795 -0.1809 0.021 Uiso 1 1 calc R . .
C3 C 1.3633(2) -0.30961(8) -0.25286(18) 0.0186(4) Uani 1 1 d . . .
H3 H 1.4424 -0.3385 -0.2927 0.022 Uiso 1 1 calc R . .
C4 C 1.3860(2) -0.24267(8) -0.26061(18) 0.0189(4) Uani 1 1 d . . .
H4 H 1.4814 -0.2246 -0.3053 0.023 Uiso 1 1 calc R . .
C5 C 1.2654(2) -0.20278(8) -0.20112(18) 0.0182(3) Uani 1 1 d . . .
H5 H 1.2767 -0.1567 -0.2049 0.022 Uiso 1 1 calc R . .
C6 C 1.1285(2) -0.23096(7) -0.13619(16) 0.0150(3) Uani 1 1 d . . .
C7 C 1.0006(2) -0.18632(7) -0.07224(17) 0.0154(3) Uani 1 1 d . . .
O8 O 1.03183(17) -0.12658(5) -0.07260(12) 0.0191(3) Uani 1 1 d . . .
N9 N 0.86075(19) -0.21219(6) -0.01800(15) 0.0181(3) Uani 1 1 d . . .
H9A H 0.7849 -0.1869 0.0200 0.022 Uiso 1 1 calc R . .
H9B H 0.8437 -0.2547 -0.0200 0.022 Uiso 1 1 calc R . .
O11 O 0.26170(17) 0.16249(5) 0.43110(14) 0.0226(3) Uani 1 1 d . . .
C12 C 0.1828(2) 0.10997(8) 0.43201(17) 0.0162(3) Uani 1 1 d . . .
C13 C 0.2380(2) 0.04896(7) 0.36278(17) 0.0161(4) Uani 1 1 d . . .
H13A H 0.1267 0.0364 0.2742 0.019 Uiso 1 1 calc R . .
H13B H 0.2580 0.0133 0.4386 0.019 Uiso 1 1 calc R . .
C14 C 0.4251(2) 0.05650(7) 0.31098(18) 0.0165(3) Uani 1 1 d . . .
H14A H 0.5355 0.0705 0.3988 0.020 Uiso 1 1 calc R . .
H14B H 0.4036 0.0912 0.2327 0.020 Uiso 1 1 calc R . .
C15 C 0.4845(2) -0.00644(7) 0.24499(18) 0.0162(3) Uani 1 1 d . . .
H15A H 0.5016 -0.0418 0.3214 0.019 Uiso 1 1 calc R . .
H15B H 0.3777 -0.0195 0.1537 0.019 Uiso 1 1 calc R . .
C16 C 0.6774(2) 0.00309(7) 0.20143(18) 0.0176(4) Uani 1 1 d . . .
H16A H 0.6614 0.0411 0.1321 0.021 Uiso 1 1 calc R . .
H16B H 0.7839 0.0139 0.2948 0.021 Uiso 1 1 calc R . .
C17 C 0.7442(2) -0.05419(7) 0.12557(17) 0.0153(3) Uani 1 1 d . . .
O18 O 0.65120(18) -0.10458(5) 0.09143(14) 0.0227(3) Uani 1 1 d . . .
O19 O 0.91533(17) -0.04254(5) 0.09649(13) 0.0206(3) Uani 1 1 d . . .
H19 H 0.9427 -0.0735 0.0456 0.031 Uiso 1 1 calc R . .
O20 O 0.03526(18) 0.10095(5) 0.49565(14) 0.0234(3) Uani 1 1 d . . .
H20 H 0.0076 0.1365 0.5306 0.035 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
N1 0.0164(7) 0.0161(7) 0.0153(6) -0.0007(5) 0.0056(5) 0.0008(5)
C2 0.0198(8) 0.0152(8) 0.0177(8) -0.0002(6) 0.0058(7) 0.0011(6)
C3 0.0173(8) 0.0209(8) 0.0181(8) -0.0007(6) 0.0059(6) 0.0049(6)
C4 0.0169(8) 0.0227(8) 0.0185(8) 0.0009(6) 0.0072(6) -0.0006(6)
C5 0.0187(8) 0.0159(8) 0.0208(8) 0.0000(6) 0.0067(7) -0.0006(6)
C6 0.0154(8) 0.0160(8) 0.0129(7) -0.0006(6) 0.0029(6) 0.0005(6)
C7 0.0158(8) 0.0165(8) 0.0133(7) 0.0011(6) 0.0030(6) 0.0010(6)
O8 0.0225(6) 0.0154(6) 0.0224(6) -0.0004(4) 0.0114(5) 0.0001(4)
N9 0.0190(7) 0.0144(7) 0.0242(7) -0.0010(5) 0.0116(6) 0.0008(5)
O11 0.0235(6) 0.0177(6) 0.0305(7) -0.0043(5) 0.0142(5) -0.0018(5)
C12 0.0151(8) 0.0186(8) 0.0145(7) 0.0015(6) 0.0033(6) 0.0020(6)
C13 0.0166(8) 0.0157(8) 0.0168(7) -0.0003(6) 0.0060(6) 0.0001(6)
C14 0.0154(8) 0.0170(8) 0.0185(8) -0.0007(6) 0.0069(6) -0.0001(6)
C15 0.0174(8) 0.0160(8) 0.0162(7) -0.0003(6) 0.0062(6) -0.0006(6)
C16 0.0189(8) 0.0165(8) 0.0193(8) -0.0024(6) 0.0085(7) -0.0016(6)
C17 0.0145(8) 0.0168(8) 0.0155(7) 0.0033(6) 0.0058(6) 0.0009(6)
O18 0.0234(6) 0.0169(6) 0.0328(7) -0.0048(5) 0.0160(5) -0.0042(5)
O19 0.0193(6) 0.0197(6) 0.0276(6) -0.0070(5) 0.0144(5) -0.0035(5)
O20 0.0269(7) 0.0174(6) 0.0330(7) -0.0038(5) 0.0202(5) 0.0001(5)

_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
N1 C2 1.340(2) . ?
N1 C6 1.343(2) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.507(2) . ?
C7 O8 1.245(2) . ?
C7 N9 1.325(2) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
O11 C12 1.212(2) . ?
C12 O20 1.3312(19) . ?
C12 C13 1.500(2) . ?
C13 C14 1.519(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.530(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.523(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.502(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 O18 1.215(2) . ?
C17 O19 1.3196(19) . ?
O19 H19 0.8400 . ?
O20 H20 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 116.96(13) . . ?
N1 C2 C3 123.92(15) . . ?
N1 C2 H2 118.0 . . ?
C3 C2 H2 118.0 . . ?
C2 C3 C4 118.63(14) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 118.16(15) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 119.29(15) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N1 C6 C5 123.03(14) . . ?
N1 C6 C7 119.05(13) . . ?
C5 C6 C7 117.92(14) . . ?
O8 C7 N9 122.96(14) . . ?
O8 C7 C6 118.25(13) . . ?
N9 C7 C6 118.79(14) . . ?
C7 N9 H9A 120.0 . . ?
C7 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
O11 C12 O20 122.49(14) . . ?
O11 C12 C13 124.58(14) . . ?
O20 C12 C13 112.93(13) . . ?
C12 C13 C14 113.03(13) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 C15 112.87(13) . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 110.62(13) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 115.57(13) . . ?
C17 C16 H16A 108.4 . . ?
C15 C16 H16A 108.4 . . ?
C17 C16 H16B 108.4 . . ?
C15 C16 H16B 108.4 . . ?
H16A C16 H16B 107.4 . . ?
O18 C17 O19 123.69(14) . . ?
O18 C17 C16 124.75(14) . . ?
O19 C17 C16 111.53(13) . . ?
C17 O19 H19 109.5 . . ?
C12 O20 H20 109.5 . . ?

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 N1 C2 C3 0.3(2) . . . . ?
N1 C2 C3 C4 0.1(2) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C2 N1 C6 C5 -0.4(2) . . . . ?
C2 N1 C6 C7 179.97(13) . . . . ?
C4 C5 C6 N1 0.1(2) . . . . ?
C4 C5 C6 C7 179.77(14) . . . . ?
N1 C6 C7 O8 175.54(14) . . . . ?
C5 C6 C7 O8 -4.2(2) . . . . ?
N1 C6 C7 N9 -4.3(2) . . . . ?
C5 C6 C7 N9 176.00(14) . . . . ?
O11 C12 C13 C14 8.7(2) . . . . ?
O20 C12 C13 C14 -171.53(13) . . . . ?
C12 C13 C14 C15 178.21(13) . . . . ?
C13 C14 C15 C16 -177.53(13) . . . . ?
C14 C15 C16 C17 -176.14(13) . . . . ?
C15 C16 C17 O18 3.8(2) . . . . ?
C15 C16 C17 O19 -177.89(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9A O18 0.88 2.12 2.9724(18) 163.4 .
N9 H9B O11 0.88 2.10 2.8891(19) 148.6 2_645
O19 H19 O8 0.84 1.76 2.5912(15) 168.1 .
O20 H20 N1 0.84 1.93 2.7512(17) 164.9 2_655

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042
_database_code_depnum_ccdc_archive 'CCDC 977788'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_STC26a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            '2:1 pico:glu'
_chemical_source_common          EtOH
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8.50 H10 N2 O3'
_chemical_formula_weight         188.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   21.95(2)
_cell_length_b                   5.220(7)
_cell_length_c                   17.260(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.86(5)
_cell_angle_gamma                90.00
_cell_volume                     1732(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2492
_cell_measurement_theta_min      4.6
_cell_measurement_theta_max      67.26

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8421
_exptl_absorpt_correction_T_max  0.9547
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8105
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_sigmaI/netI    0.0606
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.60
_diffrn_reflns_theta_max         66.58
_reflns_number_total             1496
_reflns_number_gt                1220
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.632 (Bruker AXS, 2003)'
_computing_cell_refinement       'Saint V7.36A (Bruker AXS, 2006)'
_computing_data_reduction        'Saint V7.36A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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)+(0.1492P)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    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1496
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0692
_refine_ls_wR_factor_ref         0.1953
_refine_ls_wR_factor_gt          0.1777
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.004

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
N1 N 0.38981(12) 0.6449(4) 0.51102(14) 0.0210(6) Uani 1 1 d . . .
C2 C 0.36651(15) 0.8333(5) 0.54203(18) 0.0223(7) Uani 1 1 d . . .
H2 H 0.3902 0.8652 0.6039 0.027 Uiso 1 1 calc R . .
C3 C 0.30979(14) 0.9846(6) 0.48909(19) 0.0233(7) Uani 1 1 d . . .
H3 H 0.2949 1.1159 0.5143 0.028 Uiso 1 1 calc R . .
C4 C 0.27533(14) 0.9416(6) 0.39947(18) 0.0225(7) Uani 1 1 d . . .
H4 H 0.2365 1.0438 0.3615 0.027 Uiso 1 1 calc R . .
C5 C 0.29824(13) 0.7458(5) 0.36501(17) 0.0195(6) Uani 1 1 d . . .
H5 H 0.2754 0.7104 0.3034 0.023 Uiso 1 1 calc R . .
C6 C 0.35536(13) 0.6045(5) 0.42341(16) 0.0179(6) Uani 1 1 d . . .
C7 C 0.38201(14) 0.3913(5) 0.38938(17) 0.0177(6) Uani 1 1 d . . .
O8 O 0.35177(10) 0.3398(4) 0.30910(11) 0.0214(5) Uani 1 1 d . . .
N9 N 0.43779(11) 0.2658(5) 0.44870(14) 0.0202(6) Uani 1 1 d . . .
H9A H 0.4551 0.1390 0.4318 0.024 Uiso 1 1 calc R . .
H9B H 0.4574 0.3094 0.5049 0.024 Uiso 1 1 calc R . .
C11 C 0.5000 -0.5343(7) 0.2500 0.0202(8) Uani 1 2 d S . .
H11A H 0.4985 -0.6465 0.2029 0.024 Uiso 0.50 1 calc PR . .
H11B H 0.5015 -0.6466 0.2971 0.024 Uiso 0.50 1 calc PR . .
C12 C 0.43284(13) -0.3788(5) 0.21142(16) 0.0194(6) Uani 1 1 d . . .
H12A H 0.4284 -0.2848 0.1591 0.023 Uiso 1 1 calc R . .
H12B H 0.3933 -0.4999 0.1903 0.023 Uiso 1 1 calc R . .
C13 C 0.42590(13) -0.1886(5) 0.27235(17) 0.0189(6) Uani 1 1 d . . .
O14 O 0.46574(10) -0.1650(4) 0.35174(12) 0.0222(5) Uani 1 1 d . . .
O15 O 0.36979(9) -0.0441(4) 0.22869(11) 0.0225(5) Uani 1 1 d . . .
H15 H 0.3668 0.0600 0.2638 0.034 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
N1 0.0204(13) 0.0246(14) 0.0175(12) 0.0006(9) 0.0088(10) 0.0010(9)
C2 0.0185(14) 0.0270(16) 0.0192(14) -0.0020(10) 0.0073(12) 0.0004(11)
C3 0.0200(15) 0.0238(16) 0.0287(15) -0.0001(11) 0.0138(12) 0.0029(11)
C4 0.0126(13) 0.0267(16) 0.0260(15) 0.0018(12) 0.0075(11) 0.0025(11)
C5 0.0104(13) 0.0264(16) 0.0178(14) 0.0015(10) 0.0036(11) -0.0019(11)
C6 0.0131(13) 0.0225(15) 0.0175(13) 0.0012(10) 0.0070(11) -0.0015(10)
C7 0.0140(13) 0.0211(14) 0.0186(13) 0.0012(10) 0.0082(10) -0.0017(10)
O8 0.0180(10) 0.0277(12) 0.0154(10) -0.0015(7) 0.0056(8) 0.0011(7)
N9 0.0138(12) 0.0257(14) 0.0175(12) -0.0012(9) 0.0046(9) 0.0040(9)
C11 0.0185(19) 0.023(2) 0.0187(19) 0.000 0.0086(16) 0.000
C12 0.0134(14) 0.0273(16) 0.0145(13) -0.0001(10) 0.0042(11) -0.0024(11)
C13 0.0140(13) 0.0243(15) 0.0179(14) 0.0030(10) 0.0074(11) -0.0019(10)
O14 0.0186(10) 0.0285(12) 0.0166(10) -0.0012(7) 0.0062(8) 0.0027(8)
O15 0.0184(10) 0.0286(12) 0.0176(10) 0.0001(8) 0.0064(8) 0.0059(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
N1 C2 1.334(4) . ?
N1 C6 1.341(4) . ?
C2 C3 1.382(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.373(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.503(4) . ?
C7 O8 1.243(3) . ?
C7 N9 1.329(4) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
C11 C12 1.526(4) . ?
C11 C12 1.526(4) 2_655 ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.506(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O14 1.225(3) . ?
C13 O15 1.326(3) . ?
O15 H15 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 116.8(2) . . ?
N1 C2 C3 123.6(3) . . ?
N1 C2 H2 118.2 . . ?
C3 C2 H2 118.2 . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 117.9(3) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
N1 C6 C5 123.9(3) . . ?
N1 C6 C7 116.3(2) . . ?
C5 C6 C7 119.8(2) . . ?
O8 C7 N9 123.4(3) . . ?
O8 C7 C6 119.8(2) . . ?
N9 C7 C6 116.9(2) . . ?
C7 N9 H9A 120.0 . . ?
C7 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C12 C11 C12 115.7(3) . 2_655 ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11A 108.4 2_655 . ?
C12 C11 H11B 108.4 . . ?
C12 C11 H11B 108.4 2_655 . ?
H11A C11 H11B 107.4 . . ?
C13 C12 C11 116.6(2) . . ?
C13 C12 H12A 108.1 . . ?
C11 C12 H12A 108.1 . . ?
C13 C12 H12B 108.1 . . ?
C11 C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
O14 C13 O15 123.0(2) . . ?
O14 C13 C12 126.1(2) . . ?
O15 C13 C12 110.9(2) . . ?
C13 O15 H15 109.5 . . ?

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 N1 C2 C3 0.1(4) . . . . ?
N1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C2 N1 C6 C5 0.1(4) . . . . ?
C2 N1 C6 C7 -179.8(2) . . . . ?
C4 C5 C6 N1 0.1(4) . . . . ?
C4 C5 C6 C7 -180.0(2) . . . . ?
N1 C6 C7 O8 178.6(2) . . . . ?
C5 C6 C7 O8 -1.4(4) . . . . ?
N1 C6 C7 N9 -1.2(4) . . . . ?
C5 C6 C7 N9 178.9(2) . . . . ?
C12 C11 C12 C13 -56.25(19) 2_655 . . . ?
C11 C12 C13 O14 -7.6(4) . . . . ?
C11 C12 C13 O15 172.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9A O14 0.88 2.19 3.037(4) 161.6 .
N9 H9B O14 0.88 2.35 3.096(4) 143.0 5_656
O15 H15 O8 0.84 1.76 2.575(4) 162.5 .

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.117
_database_code_depnum_ccdc_archive 'CCDC 977789'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_STC27a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            'pico form I'
_chemical_source_common          EE/isohex
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H6 N2 O'
_chemical_formula_weight         122.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   5.2870(10)
_cell_length_b                   11.163(2)
_cell_length_c                   19.899(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.704(9)
_cell_angle_gamma                90.00
_cell_volume                     1166.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5038
_cell_measurement_theta_min      4.47
_cell_measurement_theta_max      68.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8871
_exptl_absorpt_correction_T_max  0.9374
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'

_exptl_special_details           
; 
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11388
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         4.47
_diffrn_reflns_theta_max         66.60
_reflns_number_total             2055
_reflns_number_gt                1783
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.632 (Bruker AXS, 2003)'
_computing_cell_refinement       'Saint V7.36A (Bruker AXS, 2006)'
_computing_data_reduction        'Saint V7.36A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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)+(0.0462P)²+0.5543P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2055
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002

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
N1 N 0.5841(3) 0.13245(12) 0.25999(7) 0.0263(3) Uani 1 1 d . . .
C2 C 0.5699(3) 0.20089(14) 0.31520(8) 0.0257(4) Uani 1 1 d . . .
H2 H 0.7044 0.1969 0.3512 0.031 Uiso 1 1 calc R . .
C3 C 0.3665(3) 0.27690(14) 0.32148(8) 0.0265(4) Uani 1 1 d . . .
H3 H 0.3618 0.3239 0.3611 0.032 Uiso 1 1 calc R . .
C4 C 0.1705(3) 0.28316(15) 0.26903(8) 0.0270(4) Uani 1 1 d . . .
H4 H 0.0296 0.3348 0.2723 0.032 Uiso 1 1 calc R . .
C5 C 0.1813(3) 0.21356(14) 0.21173(8) 0.0237(3) Uani 1 1 d . . .
H5 H 0.0484 0.2166 0.1752 0.028 Uiso 1 1 calc R . .
C6 C 0.3901(3) 0.13955(13) 0.20887(7) 0.0202(3) Uani 1 1 d . . .
C7 C 0.4076(3) 0.06266(13) 0.14764(7) 0.0209(3) Uani 1 1 d . . .
O8 O 0.2302(2) 0.05656(10) 0.10147(5) 0.0253(3) Uani 1 1 d . . .
N9 N 0.6228(2) 0.00228(11) 0.14786(6) 0.0218(3) Uani 1 1 d . . .
H9A H 0.6454 -0.0454 0.1139 0.026 Uiso 1 1 calc R . .
H9B H 0.7434 0.0098 0.1820 0.026 Uiso 1 1 calc R . .
N11 N 0.3167(2) -0.31272(12) -0.09306(7) 0.0255(3) Uani 1 1 d . . .
C12 C 0.3446(3) -0.40354(15) -0.13535(8) 0.0292(4) Uani 1 1 d . . .
H12 H 0.2122 -0.4179 -0.1710 0.035 Uiso 1 1 calc R . .
C13 C 0.5557(3) -0.47787(15) -0.13016(8) 0.0283(4) Uani 1 1 d . . .
H13 H 0.5666 -0.5419 -0.1612 0.034 Uiso 1 1 calc R . .
C14 C 0.7493(3) -0.45679(15) -0.07901(9) 0.0304(4) Uani 1 1 d . . .
H14 H 0.8969 -0.5060 -0.0742 0.036 Uiso 1 1 calc R . .
C15 C 0.7258(3) -0.36254(15) -0.03465(8) 0.0283(4) Uani 1 1 d . . .
H15 H 0.8571 -0.3455 0.0008 0.034 Uiso 1 1 calc R . .
C16 C 0.5058(3) -0.29387(13) -0.04344(7) 0.0215(3) Uani 1 1 d . . .
C17 C 0.4764(3) -0.19162(14) 0.00432(8) 0.0237(3) Uani 1 1 d . . .
O18 O 0.6483(2) -0.17193(11) 0.05105(5) 0.0325(3) Uani 1 1 d . . .
N19 N 0.2624(3) -0.12900(12) -0.00600(7) 0.0258(3) Uani 1 1 d . . .
H19A H 0.2356 -0.0693 0.0212 0.031 Uiso 1 1 calc R . .
H19B H 0.1472 -0.1471 -0.0400 0.031 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
N1 0.0273(7) 0.0268(7) 0.0243(7) -0.0005(6) 0.0010(6) 0.0002(6)
C2 0.0289(8) 0.0267(8) 0.0204(8) -0.0030(6) -0.0012(6) -0.0007(7)
C3 0.0333(8) 0.0241(8) 0.0226(8) -0.0045(6) 0.0044(6) -0.0018(7)
C4 0.0279(8) 0.0244(8) 0.0292(8) -0.0029(7) 0.0056(7) 0.0040(7)
C5 0.0240(8) 0.0236(8) 0.0229(8) 0.0002(6) 0.0008(6) -0.0003(6)
C6 0.0216(7) 0.0185(7) 0.0209(7) 0.0031(6) 0.0045(6) -0.0018(6)
C7 0.0267(8) 0.0171(7) 0.0197(7) 0.0033(6) 0.0059(6) -0.0012(6)
O8 0.0266(6) 0.0242(6) 0.0247(6) -0.0025(4) 0.0015(5) 0.0016(5)
N9 0.0258(7) 0.0241(7) 0.0157(6) -0.0003(5) 0.0034(5) 0.0080(5)
N11 0.0262(7) 0.0232(7) 0.0264(7) -0.0036(5) 0.0002(5) 0.0009(6)
C12 0.0312(9) 0.0253(8) 0.0302(9) -0.0058(7) -0.0007(7) -0.0001(7)
C13 0.0341(9) 0.0210(8) 0.0307(9) -0.0032(7) 0.0074(7) 0.0010(7)
C14 0.0284(8) 0.0259(8) 0.0371(9) 0.0012(7) 0.0042(7) 0.0065(7)
C15 0.0288(8) 0.0266(8) 0.0282(8) 0.0014(7) -0.0022(7) 0.0017(7)
C16 0.0259(8) 0.0193(7) 0.0195(7) 0.0030(6) 0.0036(6) -0.0020(6)
C17 0.0327(8) 0.0213(8) 0.0175(7) 0.0031(6) 0.0046(6) -0.0017(7)
O18 0.0431(7) 0.0317(6) 0.0203(6) -0.0024(5) -0.0062(5) 0.0024(5)
N19 0.0320(7) 0.0238(7) 0.0221(7) -0.0043(5) 0.0048(5) 0.0023(6)

_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
N1 C2 1.348(2) . ?
N1 C6 1.360(2) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.386(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.502(2) . ?
C7 O8 1.2357(18) . ?
C7 N9 1.3220(19) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
N11 C12 1.337(2) . ?
N11 C16 1.337(2) . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.505(2) . ?
C17 O18 1.2415(19) . ?
C17 N19 1.325(2) . ?
N19 H19A 0.8800 . ?
N19 H19B 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 117.90(13) . . ?
N1 C2 C3 122.55(14) . . ?
N1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C4 C3 C2 118.89(14) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 119.53(15) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 118.51(15) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
N1 C6 C5 122.62(14) . . ?
N1 C6 C7 117.46(13) . . ?
C5 C6 C7 119.92(13) . . ?
O8 C7 N9 123.55(14) . . ?
O8 C7 C6 121.43(13) . . ?
N9 C7 C6 115.02(13) . . ?
C7 N9 H9A 120.0 . . ?
C7 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C12 N11 C16 117.15(14) . . ?
N11 C12 C13 123.70(15) . . ?
N11 C12 H12 118.2 . . ?
C13 C12 H12 118.2 . . ?
C14 C13 C12 118.41(15) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 119.05(15) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 118.33(15) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
N11 C16 C15 123.36(14) . . ?
N11 C16 C17 117.54(13) . . ?
C15 C16 C17 119.10(14) . . ?
O18 C17 N19 124.03(15) . . ?
O18 C17 C16 119.13(14) . . ?
N19 C17 C16 116.83(14) . . ?
C17 N19 H19A 120.0 . . ?
C17 N19 H19B 120.0 . . ?
H19A N19 H19B 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
C6 N1 C2 C3 0.2(2) . . . . ?
N1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C2 N1 C6 C5 -0.1(2) . . . . ?
C2 N1 C6 C7 -179.85(13) . . . . ?
C4 C5 C6 N1 0.1(2) . . . . ?
C4 C5 C6 C7 179.81(14) . . . . ?
N1 C6 C7 O8 174.07(13) . . . . ?
C5 C6 C7 O8 -5.7(2) . . . . ?
N1 C6 C7 N9 -5.09(19) . . . . ?
C5 C6 C7 N9 175.18(13) . . . . ?
C16 N11 C12 C13 0.2(2) . . . . ?
N11 C12 C13 C14 -0.6(3) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C12 N11 C16 C15 0.6(2) . . . . ?
C12 N11 C16 C17 179.85(14) . . . . ?
C14 C15 C16 N11 -1.0(2) . . . . ?
C14 C15 C16 C17 179.75(15) . . . . ?
N11 C16 C17 O18 179.82(14) . . . . ?
C15 C16 C17 O18 -0.9(2) . . . . ?
N11 C16 C17 N19 1.0(2) . . . . ?
C15 C16 C17 N19 -179.75(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9A O18 0.88 1.89 2.7518(17) 167.0 .
N19 H19A O8 0.88 2.13 2.9965(17) 167.8 .
N19 H19B O8 0.88 2.43 3.1450(18) 138.1 3

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 977790'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_STC28b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            '1:1 pico:man'
_chemical_source_common          EE/isohex
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2 O4'
_chemical_formula_weight         274.27
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   5.390(2)
_cell_length_b                   9.897(3)
_cell_length_c                   24.214(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.699(13)
_cell_angle_gamma                90.00
_cell_volume                     1291.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      68.09

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8107
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'

_exptl_special_details           
; 
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            45411
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         66.57
_reflns_number_total             4517
_reflns_number_gt                4365
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.632 (Bruker AXS, 2003)'
_computing_cell_refinement       'Saint V7.36A (Bruker AXS, 2006)'
_computing_data_reduction        'Saint V7.36A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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)+(0.0384P)²+0.2696P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_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   0.07(12)
_refine_ls_number_reflns         4517
_refine_ls_number_parameters     365
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0271
_refine_ls_wR_factor_ref         0.0708
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.008
_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
N1 N 0.0926(2) 1.04180(14) 0.15109(5) 0.0202(3) Uani 1 1 d . . .
C2 C -0.0952(3) 1.06547(16) 0.11588(6) 0.0216(3) Uani 1 1 d . . .
H2 H -0.1111 1.1534 0.1005 0.026 Uiso 1 1 calc R . .
C3 C -0.2684(3) 0.96817(17) 0.10065(6) 0.0220(3) Uani 1 1 d . . .
H3 H -0.3977 0.9888 0.0750 0.026 Uiso 1 1 calc R . .
C4 C -0.2490(3) 0.84029(17) 0.12360(6) 0.0217(3) Uani 1 1 d . . .
H4 H -0.3653 0.7718 0.1141 0.026 Uiso 1 1 calc R . .
C5 C -0.0563(3) 0.81403(16) 0.16073(6) 0.0200(3) Uani 1 1 d . . .
H5 H -0.0385 0.7276 0.1773 0.024 Uiso 1 1 calc R . .
C6 C 0.1086(3) 0.91692(16) 0.17285(6) 0.0176(3) Uani 1 1 d . . .
C7 C 0.3209(3) 0.89498(16) 0.21280(6) 0.0174(3) Uani 1 1 d . . .
O8 O 0.3665(2) 0.77879(11) 0.23140(4) 0.0212(2) Uani 1 1 d . . .
N9 N 0.4492(2) 1.00287(14) 0.22664(5) 0.0202(3) Uani 1 1 d . . .
H9A H 0.5746 0.9960 0.2501 0.024 Uiso 1 1 calc R . .
H9B H 0.4098 1.0820 0.2124 0.024 Uiso 1 1 calc R . .
C10 C 1.1654(3) 0.59988(16) 0.42745(6) 0.0212(3) Uani 1 1 d . . .
H10 H 1.3156 0.5766 0.4097 0.025 Uiso 1 1 calc R . .
C11 C 1.1003(3) 0.53405(17) 0.47590(7) 0.0268(4) Uani 1 1 d . . .
H11 H 1.2054 0.4660 0.4909 0.032 Uiso 1 1 calc R . .
C12 C 0.8823(3) 0.56783(18) 0.50216(6) 0.0284(4) Uani 1 1 d . . .
H12 H 0.8361 0.5224 0.5350 0.034 Uiso 1 1 calc R . .
C13 C 0.7318(3) 0.66856(19) 0.48010(6) 0.0267(4) Uani 1 1 d . . .
H13 H 0.5836 0.6933 0.4984 0.032 Uiso 1 1 calc R . .
C14 C 0.7964(3) 0.73342(17) 0.43147(6) 0.0218(3) Uani 1 1 d . . .
H14 H 0.6914 0.8016 0.4164 0.026 Uiso 1 1 calc R . .
C15 C 1.0139(3) 0.69903(14) 0.40475(6) 0.0178(3) Uani 1 1 d . . .
C16 C 1.0988(3) 0.76957(16) 0.35275(6) 0.0188(3) Uani 1 1 d . . .
H16 H 1.2014 0.7041 0.3314 0.023 Uiso 1 1 calc R . .
O17 O 1.2537(2) 0.87962(12) 0.36807(5) 0.0283(3) Uani 1 1 d . . .
H17 H 1.2024 0.9504 0.3525 0.042 Uiso 1 1 calc R . .
C18 C 0.8864(3) 0.81668(16) 0.31516(6) 0.0184(3) Uani 1 1 d . . .
O19 O 0.8693(2) 0.93414(11) 0.30041(4) 0.0212(2) Uani 1 1 d . . .
O20 O 0.7361(2) 0.71921(11) 0.29988(5) 0.0215(2) Uani 1 1 d . . .
H20 H 0.6274 0.7501 0.2782 0.032 Uiso 1 1 calc R . .
N21 N 1.3720(2) 1.17126(14) 0.34619(5) 0.0207(3) Uani 1 1 d . . .
C22 C 1.5555(3) 1.15338(16) 0.38304(6) 0.0222(3) Uani 1 1 d . . .
H22 H 1.5723 1.0672 0.4000 0.027 Uiso 1 1 calc R . .
C23 C 1.7228(3) 1.25385(17) 0.39796(7) 0.0244(4) Uani 1 1 d . . .
H23 H 1.8490 1.2370 0.4248 0.029 Uiso 1 1 calc R . .
C24 C 1.7023(3) 1.37894(18) 0.37299(7) 0.0239(4) Uani 1 1 d . . .
H24 H 1.8149 1.4495 0.3822 0.029 Uiso 1 1 calc R . .
C25 C 1.5148(3) 1.39984(17) 0.33430(6) 0.0222(3) Uani 1 1 d . . .
H25 H 1.4972 1.4845 0.3162 0.027 Uiso 1 1 calc R . .
C26 C 1.3537(3) 1.29429(16) 0.32270(6) 0.0182(3) Uani 1 1 d . . .
C27 C 1.1449(3) 1.31567(16) 0.28216(6) 0.0196(3) Uani 1 1 d . . .
O28 O 1.1116(2) 1.43060(11) 0.26188(5) 0.0255(3) Uani 1 1 d . . .
N29 N 1.0056(2) 1.21051(13) 0.27043(5) 0.0213(3) Uani 1 1 d . . .
H29A H 0.8802 1.2186 0.2471 0.026 Uiso 1 1 calc R . .
H29B H 1.0376 1.1319 0.2860 0.026 Uiso 1 1 calc R . .
C30 C 0.7484(3) 1.46554(17) 0.06786(7) 0.0241(4) Uani 1 1 d . . .
H30 H 0.8134 1.5387 0.0889 0.029 Uiso 1 1 calc R . .
C31 C 0.8658(3) 1.42587(18) 0.01980(7) 0.0277(4) Uani 1 1 d . . .
H31 H 1.0095 1.4726 0.0078 0.033 Uiso 1 1 calc R . .
C32 C 0.7735(3) 1.31801(19) -0.01080(7) 0.0290(4) Uani 1 1 d . . .
H32 H 0.8536 1.2909 -0.0437 0.035 Uiso 1 1 calc R . .
C33 C 0.5648(3) 1.25021(17) 0.00677(7) 0.0283(4) Uani 1 1 d . . .
H33 H 0.5022 1.1759 -0.0140 0.034 Uiso 1 1 calc R . .
C34 C 0.4459(3) 1.29031(17) 0.05473(6) 0.0240(3) Uani 1 1 d . . .
H34 H 0.3024 1.2433 0.0666 0.029 Uiso 1 1 calc R . .
C35 C 0.5359(3) 1.39868(16) 0.08532(6) 0.0202(3) Uani 1 1 d . . .
C36 C 0.4138(3) 1.44085(16) 0.13899(6) 0.0211(3) Uani 1 1 d . . .
H36 H 0.2542 1.3905 0.1430 0.025 Uiso 1 1 calc R . .
O37 O 0.3636(2) 1.58122(11) 0.13729(4) 0.0247(2) Uani 1 1 d . . .
H37 H 0.3749 1.6134 0.1693 0.037 Uiso 1 1 calc R . .
C38 C 0.5914(3) 1.39950(16) 0.18531(6) 0.0194(3) Uani 1 1 d . . .
O39 O 0.5999(2) 1.28216(11) 0.20095(4) 0.0233(2) Uani 1 1 d . . .
O40 O 0.7345(2) 1.49733(11) 0.20313(5) 0.0247(3) Uani 1 1 d . . .
H40 H 0.8439 1.4657 0.2245 0.037 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
N1 0.0214(7) 0.0198(7) 0.0194(7) 0.0009(5) 0.0003(5) 0.0000(5)
C2 0.0234(8) 0.0202(8) 0.0213(8) 0.0022(7) 0.0005(6) 0.0018(6)
C3 0.0193(8) 0.0268(9) 0.0198(8) -0.0010(6) -0.0013(6) 0.0017(6)
C4 0.0200(8) 0.0226(8) 0.0226(8) -0.0054(6) 0.0029(6) -0.0031(6)
C5 0.0225(8) 0.0176(8) 0.0198(7) -0.0002(6) 0.0033(6) -0.0008(6)
C6 0.0198(7) 0.0180(8) 0.0150(7) -0.0016(6) 0.0031(6) 0.0007(6)
C7 0.0197(7) 0.0166(8) 0.0159(7) -0.0005(6) 0.0041(6) 0.0006(6)
O8 0.0242(6) 0.0178(6) 0.0215(5) 0.0033(5) -0.0016(4) -0.0005(4)
N9 0.0226(7) 0.0167(7) 0.0212(7) 0.0007(5) -0.0039(5) 0.0009(5)
C10 0.0196(8) 0.0206(8) 0.0234(8) -0.0015(6) -0.0032(6) -0.0002(6)
C11 0.0328(9) 0.0239(8) 0.0234(8) 0.0051(7) -0.0105(7) -0.0025(7)
C12 0.0338(10) 0.0342(10) 0.0171(7) 0.0050(7) -0.0041(6) -0.0126(7)
C13 0.0259(9) 0.0352(9) 0.0190(7) -0.0028(7) 0.0006(6) -0.0078(7)
C14 0.0204(8) 0.0237(8) 0.0215(8) -0.0020(6) 0.0000(6) 0.0002(6)
C15 0.0191(7) 0.0165(8) 0.0178(7) -0.0020(6) -0.0034(6) -0.0037(6)
C16 0.0165(8) 0.0181(8) 0.0219(8) 0.0021(6) 0.0008(6) -0.0020(6)
O17 0.0255(6) 0.0229(6) 0.0361(6) 0.0112(5) -0.0118(5) -0.0098(5)
C18 0.0206(8) 0.0194(8) 0.0153(7) 0.0006(6) 0.0017(6) -0.0010(6)
O19 0.0238(6) 0.0163(6) 0.0234(6) 0.0029(5) -0.0023(4) -0.0015(4)
O20 0.0238(6) 0.0177(6) 0.0228(6) 0.0030(4) -0.0064(4) -0.0041(4)
N21 0.0248(7) 0.0187(7) 0.0186(6) 0.0002(5) 0.0016(5) -0.0009(5)
C22 0.0255(8) 0.0203(8) 0.0207(8) 0.0017(7) 0.0005(6) 0.0014(6)
C23 0.0246(9) 0.0287(10) 0.0200(8) -0.0018(7) -0.0018(6) 0.0006(7)
C24 0.0235(9) 0.0225(8) 0.0257(8) -0.0052(7) 0.0002(7) -0.0042(6)
C25 0.0275(8) 0.0168(8) 0.0223(8) -0.0017(6) 0.0030(6) 0.0002(6)
C26 0.0205(7) 0.0170(8) 0.0172(7) -0.0022(6) 0.0038(6) 0.0011(6)
C27 0.0212(8) 0.0176(8) 0.0201(7) 0.0002(6) 0.0026(6) 0.0024(6)
O28 0.0256(6) 0.0188(6) 0.0320(6) 0.0056(5) -0.0045(5) -0.0016(5)
N29 0.0227(7) 0.0173(7) 0.0238(7) 0.0003(5) -0.0047(5) -0.0009(5)
C30 0.0267(8) 0.0212(8) 0.0243(8) 0.0021(6) -0.0018(6) 0.0000(6)
C31 0.0241(8) 0.0322(9) 0.0267(8) 0.0057(7) 0.0012(6) 0.0029(7)
C32 0.0327(9) 0.0369(10) 0.0173(8) 0.0007(7) 0.0004(6) 0.0100(7)
C33 0.0338(10) 0.0284(9) 0.0226(8) -0.0032(7) -0.0084(7) 0.0029(7)
C34 0.0229(8) 0.0244(8) 0.0247(8) 0.0025(7) -0.0040(6) -0.0002(6)
C35 0.0201(8) 0.0189(8) 0.0216(8) 0.0033(6) -0.0035(6) 0.0033(6)
C36 0.0202(8) 0.0202(8) 0.0228(8) 0.0005(6) 0.0008(6) -0.0004(6)
O37 0.0300(6) 0.0205(6) 0.0237(6) -0.0014(4) -0.0019(5) 0.0051(5)
C38 0.0197(8) 0.0189(8) 0.0198(7) -0.0008(6) 0.0039(6) -0.0005(6)
O39 0.0269(6) 0.0194(6) 0.0237(6) 0.0035(5) -0.0027(4) -0.0023(5)
O40 0.0275(6) 0.0202(6) 0.0263(6) 0.0017(5) -0.0072(5) -0.0022(5)

_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
N1 C2 1.336(2) . ?
N1 C6 1.346(2) . ?
C2 C3 1.388(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.505(2) . ?
C7 O8 1.2581(19) . ?
C7 N9 1.313(2) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
C10 C15 1.386(2) . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.515(2) . ?
C16 O17 1.4190(19) . ?
C16 C18 1.527(2) . ?
C16 H16 1.0000 . ?
O17 H17 0.8400 . ?
C18 O19 1.2193(19) . ?
C18 O20 1.3102(19) . ?
O20 H20 0.8400 . ?
N21 C22 1.335(2) . ?
N21 C26 1.347(2) . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.500(2) . ?
C27 O28 1.251(2) . ?
C27 N29 1.312(2) . ?
N29 H29A 0.8800 . ?
N29 H29B 0.8800 . ?
C30 C31 1.388(2) . ?
C30 C35 1.393(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.388(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.382(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.391(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.388(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.522(2) . ?
C36 O37 1.416(2) . ?
C36 C38 1.522(2) . ?
C36 H36 1.0000 . ?
O37 H37 0.8400 . ?
C38 O39 1.222(2) . ?
C38 O40 1.3078(19) . ?
O40 H40 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 117.07(13) . . ?
N1 C2 C3 123.35(15) . . ?
N1 C2 H2 118.3 . . ?
C3 C2 H2 118.3 . . ?
C4 C3 C2 118.68(14) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 118.85(15) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 118.26(15) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
N1 C6 C5 123.78(14) . . ?
N1 C6 C7 115.38(13) . . ?
C5 C6 C7 120.83(14) . . ?
O8 C7 N9 123.50(14) . . ?
O8 C7 C6 120.37(13) . . ?
N9 C7 C6 116.13(13) . . ?
C7 N9 H9A 120.0 . . ?
C7 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
C15 C10 C11 120.86(15) . . ?
C15 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 119.92(15) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 119.49(15) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 120.43(16) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C15 C14 C13 120.25(16) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C10 C15 C14 119.04(14) . . ?
C10 C15 C16 118.27(14) . . ?
C14 C15 C16 122.64(14) . . ?
O17 C16 C15 108.61(12) . . ?
O17 C16 C18 110.85(12) . . ?
C15 C16 C18 113.86(12) . . ?
O17 C16 H16 107.8 . . ?
C15 C16 H16 107.8 . . ?
C18 C16 H16 107.8 . . ?
C16 O17 H17 109.5 . . ?
O19 C18 O20 125.10(14) . . ?
O19 C18 C16 121.29(13) . . ?
O20 C18 C16 113.58(13) . . ?
C18 O20 H20 109.5 . . ?
C22 N21 C26 116.86(14) . . ?
N21 C22 C23 123.55(15) . . ?
N21 C22 H22 118.2 . . ?
C23 C22 H22 118.2 . . ?
C24 C23 C22 118.67(15) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C25 118.94(15) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C26 C25 C24 118.35(15) . . ?
C26 C25 H25 120.8 . . ?
C24 C25 H25 120.8 . . ?
N21 C26 C25 123.61(14) . . ?
N21 C26 C27 117.03(14) . . ?
C25 C26 C27 119.35(14) . . ?
O28 C27 N29 123.88(14) . . ?
O28 C27 C26 119.21(14) . . ?
N29 C27 C26 116.91(14) . . ?
C27 N29 H29A 120.0 . . ?
C27 N29 H29B 120.0 . . ?
H29A N29 H29B 120.0 . . ?
C31 C30 C35 120.33(16) . . ?
C31 C30 H30 119.8 . . ?
C35 C30 H30 119.8 . . ?
C30 C31 C32 120.07(16) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 H31 120.0 . . ?
C33 C32 C31 119.80(15) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C34 120.24(16) . . ?
C32 C33 H33 119.9 . . ?
C34 C33 H33 119.9 . . ?
C35 C34 C33 120.31(16) . . ?
C35 C34 H34 119.8 . . ?
C33 C34 H34 119.8 . . ?
C34 C35 C30 119.24(15) . . ?
C34 C35 C36 121.05(14) . . ?
C30 C35 C36 119.64(14) . . ?
O37 C36 C38 113.81(13) . . ?
O37 C36 C35 109.18(13) . . ?
C38 C36 C35 106.31(12) . . ?
O37 C36 H36 109.1 . . ?
C38 C36 H36 109.1 . . ?
C35 C36 H36 109.1 . . ?
C36 O37 H37 109.5 . . ?
O39 C38 O40 125.56(14) . . ?
O39 C38 C36 120.31(14) . . ?
O40 C38 C36 114.03(14) . . ?
C38 O40 H40 109.5 . . ?

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 N1 C2 C3 -0.9(2) . . . . ?
N1 C2 C3 C4 1.0(2) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C2 N1 C6 C5 0.1(2) . . . . ?
C2 N1 C6 C7 -179.30(13) . . . . ?
C4 C5 C6 N1 0.5(2) . . . . ?
C4 C5 C6 C7 179.89(13) . . . . ?
N1 C6 C7 O8 -173.23(14) . . . . ?
C5 C6 C7 O8 7.4(2) . . . . ?
N1 C6 C7 N9 7.30(19) . . . . ?
C5 C6 C7 N9 -172.09(14) . . . . ?
C15 C10 C11 C12 -0.3(2) . . . . ?
C10 C11 C12 C13 -0.7(2) . . . . ?
C11 C12 C13 C14 1.2(2) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C11 C10 C15 C14 0.8(2) . . . . ?
C11 C10 C15 C16 178.37(14) . . . . ?
C13 C14 C15 C10 -0.3(2) . . . . ?
C13 C14 C15 C16 -177.76(14) . . . . ?
C10 C15 C16 O17 -86.34(17) . . . . ?
C14 C15 C16 O17 91.11(16) . . . . ?
C10 C15 C16 C18 149.63(14) . . . . ?
C14 C15 C16 C18 -32.9(2) . . . . ?
O17 C16 C18 O19 2.4(2) . . . . ?
C15 C16 C18 O19 125.16(15) . . . . ?
O17 C16 C18 O20 -179.66(12) . . . . ?
C15 C16 C18 O20 -56.86(18) . . . . ?
C26 N21 C22 C23 0.3(2) . . . . ?
N21 C22 C23 C24 -1.0(3) . . . . ?
C22 C23 C24 C25 0.4(2) . . . . ?
C23 C24 C25 C26 0.7(2) . . . . ?
C22 N21 C26 C25 0.8(2) . . . . ?
C22 N21 C26 C27 -178.78(13) . . . . ?
C24 C25 C26 N21 -1.4(2) . . . . ?
C24 C25 C26 C27 178.26(14) . . . . ?
N21 C26 C27 O28 175.67(14) . . . . ?
C25 C26 C27 O28 -4.0(2) . . . . ?
N21 C26 C27 N29 -3.9(2) . . . . ?
C25 C26 C27 N29 176.49(14) . . . . ?
C35 C30 C31 C32 -0.8(2) . . . . ?
C30 C31 C32 C33 -0.1(2) . . . . ?
C31 C32 C33 C34 0.5(2) . . . . ?
C32 C33 C34 C35 0.0(2) . . . . ?
C33 C34 C35 C30 -0.9(2) . . . . ?
C33 C34 C35 C36 -177.79(14) . . . . ?
C31 C30 C35 C34 1.3(2) . . . . ?
C31 C30 C35 C36 178.23(14) . . . . ?
C34 C35 C36 O37 -128.88(15) . . . . ?
C30 C35 C36 O37 54.23(18) . . . . ?
C34 C35 C36 C38 107.95(15) . . . . ?
C30 C35 C36 C38 -68.94(18) . . . . ?
O37 C36 C38 O39 160.39(15) . . . . ?
C35 C36 C38 O39 -79.39(18) . . . . ?
O37 C36 C38 O40 -22.95(19) . . . . ?
C35 C36 C38 O40 97.27(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9A O19 0.88 2.08 2.9465(18) 167.0 .
N9 H9B O39 0.88 2.25 2.9495(19) 136.4 .
O17 H17 O19 0.84 2.19 2.6803(16) 117.4 .
O17 H17 N21 0.84 2.38 3.004(2) 132.2 .
O20 H20 O8 0.84 1.82 2.6431(16) 167.3 .
N29 H29A O39 0.88 1.97 2.8330(19) 166.1 .
N29 H29B O19 0.88 2.19 2.9259(19) 141.2 .
O37 H37 O8 0.84 2.22 3.0026(16) 154.4 1_565
O40 H40 O28 0.84 1.73 2.5536(16) 166.4 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        66.57
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 977791'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_STC29a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;


_chemical_name_common            '1:1 pico:mal'
_chemical_source_common          EE/isohex
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 N2 O5'
_chemical_formula_weight         226.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.1660(10)
_cell_length_b                   7.666(2)
_cell_length_c                   13.086(3)
_cell_angle_alpha                74.730(11)
_cell_angle_beta                 81.423(12)
_cell_angle_gamma                77.409(13)
_cell_volume                     485.60(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5335
_cell_measurement_theta_min      3.52
_cell_measurement_theta_max      68.33

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             236
_exptl_absorpt_coefficient_mu    1.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8607
_exptl_absorpt_correction_T_max  0.9267
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2010)'

_exptl_special_details           
; 
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         microsource
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device_type  'three-circle goniometer'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3645
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         66.57
_reflns_number_total             1610
_reflns_number_gt                1501
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART V5.632 (Bruker AXS, 2003)'
_computing_cell_refinement       'Saint V7.36A (Bruker AXS, 2006)'
_computing_data_reduction        'Saint V7.36A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_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)+(0.0512P)²+0.1490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1610
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.004

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
N1 N 0.1814(2) 0.53155(14) 0.10643(8) 0.0171(3) Uani 1 1 d . . .
C2 C 0.1295(3) 0.42463(17) 0.20296(10) 0.0192(3) Uani 1 1 d . . .
H2 H 0.2641 0.3234 0.2297 0.023 Uiso 1 1 calc R . .
C3 C -0.1087(3) 0.45257(18) 0.26631(10) 0.0187(3) Uani 1 1 d . . .
H3 H -0.1365 0.3710 0.3338 0.022 Uiso 1 1 calc R . .
C4 C -0.3049(3) 0.60105(18) 0.22957(10) 0.0184(3) Uani 1 1 d . . .
H4 H -0.4691 0.6248 0.2717 0.022 Uiso 1 1 calc R . .
C5 C -0.2565(3) 0.71507(17) 0.12955(10) 0.0177(3) Uani 1 1 d . . .
H5 H -0.3869 0.8183 0.1017 0.021 Uiso 1 1 calc R . .
C6 C -0.0135(2) 0.67437(17) 0.07157(10) 0.0155(3) Uani 1 1 d . . .
C7 C 0.0415(3) 0.79255(16) -0.03781(10) 0.0158(3) Uani 1 1 d . . .
O8 O -0.14117(18) 0.91695(11) -0.07752(7) 0.0200(2) Uani 1 1 d . . .
N9 N 0.2819(2) 0.75748(15) -0.08738(8) 0.0195(3) Uani 1 1 d . . .
H9A H 0.3203 0.8233 -0.1518 0.023 Uiso 1 1 calc R . .
H9B H 0.4038 0.6683 -0.0560 0.023 Uiso 1 1 calc R . .
O11 O 0.42211(19) 1.32521(12) -0.54026(8) 0.0257(3) Uani 1 1 d . . .
C12 C 0.2601(2) 1.22555(16) -0.51856(9) 0.0168(3) Uani 1 1 d . . .
C13 C 0.0236(3) 1.24222(17) -0.43670(10) 0.0178(3) Uani 1 1 d . . .
H13A H -0.1352 1.2280 -0.4655 0.021 Uiso 1 1 calc R . .
H13B H -0.0114 1.3669 -0.4234 0.021 Uiso 1 1 calc R . .
C14 C 0.0637(2) 1.10078(16) -0.33230(10) 0.0158(3) Uani 1 1 d . . .
O15 O 0.27092(17) 0.98973(12) -0.31305(7) 0.0191(2) Uani 1 1 d . . .
O16 O -0.14676(17) 1.11500(12) -0.26437(7) 0.0204(2) Uani 1 1 d . . .
H16 H -0.1154 1.0397 -0.2061 0.031 Uiso 1 1 calc R . .
O17 O 0.26849(17) 1.08882(12) -0.56485(7) 0.0187(2) Uani 1 1 d . . .
H17 H 0.4125 1.0744 -0.6037 0.028 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
N1 0.0152(6) 0.0194(5) 0.0159(5) -0.0042(4) -0.0016(4) -0.0015(4)
C2 0.0172(7) 0.0203(7) 0.0177(6) -0.0021(5) -0.0032(5) -0.0008(5)
C3 0.0204(7) 0.0208(6) 0.0151(6) -0.0027(5) -0.0024(5) -0.0054(5)
C4 0.0146(7) 0.0227(7) 0.0182(6) -0.0069(5) 0.0018(5) -0.0041(5)
C5 0.0161(7) 0.0174(6) 0.0190(6) -0.0047(5) -0.0024(5) -0.0007(5)
C6 0.0154(6) 0.0173(6) 0.0149(6) -0.0050(5) -0.0022(5) -0.0038(5)
C7 0.0160(6) 0.0161(6) 0.0162(6) -0.0055(5) -0.0018(5) -0.0025(5)
O8 0.0179(5) 0.0204(5) 0.0172(5) -0.0013(4) -0.0001(3) 0.0012(4)
N9 0.0169(6) 0.0206(6) 0.0161(5) 0.0007(4) 0.0001(4) 0.0000(4)
O11 0.0223(5) 0.0224(5) 0.0318(5) -0.0049(4) 0.0017(4) -0.0079(4)
C12 0.0176(7) 0.0153(6) 0.0146(6) 0.0007(5) -0.0049(5) -0.0001(5)
C13 0.0186(7) 0.0165(6) 0.0162(6) -0.0025(5) -0.0018(5) -0.0007(5)
C14 0.0167(7) 0.0157(6) 0.0161(6) -0.0054(5) -0.0013(5) -0.0036(5)
O15 0.0166(5) 0.0203(5) 0.0164(5) -0.0020(4) 0.0000(3) 0.0009(4)
O16 0.0168(5) 0.0240(5) 0.0146(5) -0.0009(4) 0.0014(3) 0.0019(4)
O17 0.0167(5) 0.0211(5) 0.0176(5) -0.0066(4) 0.0012(3) -0.0020(4)

_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
N1 C2 1.3374(17) . ?
N1 C6 1.3467(17) . ?
C2 C3 1.3862(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3814(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3909(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3853(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.5027(17) . ?
C7 O8 1.2500(15) . ?
C7 N9 1.3198(17) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
O11 C12 1.2078(16) . ?
C12 O17 1.3320(16) . ?
C12 C13 1.5065(18) . ?
C13 C14 1.5137(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O15 1.2264(15) . ?
C14 O16 1.3021(16) . ?
O16 H16 0.8400 . ?
O17 H17 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 116.25(11) . . ?
N1 C2 C3 123.98(12) . . ?
N1 C2 H2 118.0 . . ?
C3 C2 H2 118.0 . . ?
C4 C3 C2 118.85(12) . . ?
C4 C3 H3 120.6 . . ?
C2 C3 H3 120.6 . . ?
C3 C4 C5 118.49(12) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C6 C5 C4 118.38(11) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N1 C6 C5 124.03(12) . . ?
N1 C6 C7 116.47(11) . . ?
C5 C6 C7 119.49(11) . . ?
O8 C7 N9 123.43(11) . . ?
O8 C7 C6 118.93(11) . . ?
N9 C7 C6 117.64(11) . . ?
C7 N9 H9A 120.0 . . ?
C7 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
O11 C12 O17 123.91(12) . . ?
O11 C12 C13 124.01(12) . . ?
O17 C12 C13 112.08(10) . . ?
C12 C13 C14 112.99(10) . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
O15 C14 O16 124.16(11) . . ?
O15 C14 C13 124.26(11) . . ?
O16 C14 C13 111.56(10) . . ?
C14 O16 H16 109.5 . . ?
C12 O17 H17 109.5 . . ?

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 N1 C2 C3 0.46(18) . . . . ?
N1 C2 C3 C4 -1.19(19) . . . . ?
C2 C3 C4 C5 0.95(18) . . . . ?
C3 C4 C5 C6 -0.09(18) . . . . ?
C2 N1 C6 C5 0.49(18) . . . . ?
C2 N1 C6 C7 -178.72(10) . . . . ?
C4 C5 C6 N1 -0.67(19) . . . . ?
C4 C5 C6 C7 178.51(11) . . . . ?
N1 C6 C7 O8 173.86(11) . . . . ?
C5 C6 C7 O8 -5.38(18) . . . . ?
N1 C6 C7 N9 -5.53(17) . . . . ?
C5 C6 C7 N9 175.23(11) . . . . ?
O11 C12 C13 C14 -101.97(14) . . . . ?
O17 C12 C13 C14 78.52(13) . . . . ?
C12 C13 C14 O15 3.73(17) . . . . ?
C12 C13 C14 O16 -178.04(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N9 H9A O15 0.88 2.18 3.0217(15) 160.3 .
N9 H9B N1 0.88 2.46 3.1725(16) 138.4 2_665
O16 H16 O8 0.84 1.70 2.5162(13) 163.6 .
O17 H17 O15 0.84 1.87 2.7065(13) 172.6 2_674

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        66.57
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 977792'
