# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 1035032'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-oxo-1,2-dihydro-3-pyridinecarboxylic acid 
;
_chemical_name_common            2-ODHPCA
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 N O3'
_chemical_formula_sum            'C6 H5 N O3'
_chemical_formula_weight         139.11

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_space_group_name_Hall           '-P 2yn'

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                   3.640(1)
_cell_length_b                   11.584(3)
_cell_length_c                   13.565(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.64(1)
_cell_angle_gamma                90.00
_cell_volume                     570.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    1370
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       'thick lath'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9613
_exptl_absorpt_correction_T_max  0.9804
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2539
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         27.47
_reflns_number_total             1307
_reflns_number_gt                971
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'

_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)+(0.0761P)²+0.1679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1307
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1300
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.5633(4) 0.25484(14) 0.33937(12) 0.0161(4) Uani 1 1 d . . .
C3 C 0.4124(4) 0.18122(14) 0.41096(12) 0.0149(4) Uani 1 1 d . . .
C4 C 0.3141(4) 0.06996(14) 0.38714(12) 0.0160(4) Uani 1 1 d . . .
H4 H 0.2153 0.0222 0.4354 0.019 Uiso 1 1 calc R . .
C5 C 0.3568(4) 0.02535(15) 0.29270(12) 0.0185(4) Uani 1 1 d . . .
H5 H 0.2937 -0.0524 0.2768 0.022 Uiso 1 1 calc R . .
C6 C 0.4913(4) 0.09673(15) 0.22447(12) 0.0179(4) Uani 1 1 d . . .
H6 H 0.5201 0.0685 0.1598 0.021 Uiso 1 1 calc R . .
C7 C 0.3601(4) 0.22936(15) 0.51047(12) 0.0175(4) Uani 1 1 d . . .
N1 N 0.5846(4) 0.20702(13) 0.24719(10) 0.0174(3) Uani 1 1 d . . .
H1 H 0.6636 0.2508 0.2003 0.021 Uiso 1 1 calc R . .
O8 O 0.4619(4) 0.33727(10) 0.52644(9) 0.0218(3) Uani 1 1 d . . .
H8 H 0.5445 0.3644 0.4752 0.033 Uiso 1 1 calc R . .
O9 O 0.2246(3) 0.17228(10) 0.57449(8) 0.0216(3) Uani 1 1 d . . .
O10 O 0.6713(3) 0.35672(10) 0.35588(9) 0.0209(3) Uani 1 1 d . . .

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
C2 0.0139(8) 0.0182(9) 0.0161(8) 0.0022(7) 0.0007(6) 0.0024(6)
C3 0.0129(8) 0.0182(8) 0.0136(8) 0.0015(6) 0.0009(6) 0.0011(6)
C4 0.0126(7) 0.0188(9) 0.0167(8) 0.0031(6) 0.0018(6) 0.0014(6)
C5 0.0177(8) 0.0174(9) 0.0202(9) -0.0016(7) 0.0003(7) 0.0015(7)
C6 0.0172(8) 0.0213(9) 0.0149(8) -0.0025(7) 0.0000(6) 0.0040(7)
C7 0.0165(8) 0.0191(9) 0.0168(8) 0.0004(7) 0.0000(6) 0.0025(6)
N1 0.0181(7) 0.0207(8) 0.0136(7) 0.0030(5) 0.0034(5) 0.0002(6)
O8 0.0286(7) 0.0202(7) 0.0168(6) -0.0020(5) 0.0038(5) -0.0013(5)
O9 0.0269(7) 0.0232(7) 0.0154(6) 0.0014(5) 0.0066(5) 0.0014(5)
O10 0.0242(7) 0.0170(7) 0.0217(6) 0.0018(5) 0.0031(5) -0.0017(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
C2 O10 1.258(2) . ?
C2 N1 1.376(2) . ?
C2 C3 1.435(2) . ?
C3 C4 1.369(2) . ?
C3 C7 1.487(2) . ?
C4 C5 1.402(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.362(2) . ?
C5 H5 0.9500 . ?
C6 N1 1.351(2) . ?
C6 H6 0.9500 . ?
C7 O9 1.2264(19) . ?
C7 O8 1.317(2) . ?
N1 H1 0.8800 . ?
O8 H8 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
O10 C2 N1 119.98(14) . . ?
O10 C2 C3 124.63(14) . . ?
N1 C2 C3 115.40(15) . . ?
C4 C3 C2 120.45(15) . . ?
C4 C3 C7 121.13(15) . . ?
C2 C3 C7 118.41(15) . . ?
C3 C4 C5 121.11(15) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 118.03(16) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
N1 C6 C5 121.11(15) . . ?
N1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
O9 C7 O8 121.29(15) . . ?
O9 C7 C3 121.94(15) . . ?
O8 C7 C3 116.77(14) . . ?
C6 N1 C2 123.82(14) . . ?
C6 N1 H1 118.1 . . ?
C2 N1 H1 118.1 . . ?
C7 O8 H8 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
O10 C2 C3 C4 -177.69(15) . . . . ?
N1 C2 C3 C4 2.5(2) . . . . ?
O10 C2 C3 C7 3.4(2) . . . . ?
N1 C2 C3 C7 -176.41(14) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C7 C3 C4 C5 178.73(15) . . . . ?
C3 C4 C5 C6 -1.5(2) . . . . ?
C4 C5 C6 N1 0.6(2) . . . . ?
C4 C3 C7 O9 -0.7(3) . . . . ?
C2 C3 C7 O9 178.23(15) . . . . ?
C4 C3 C7 O8 -179.82(15) . . . . ?
C2 C3 C7 O8 -0.9(2) . . . . ?
C5 C6 N1 C2 2.0(2) . . . . ?
O10 C2 N1 C6 176.74(15) . . . . ?
C3 C2 N1 C6 -3.5(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
N1 H1 O9 0.88 1.95 2.8100(18) 164.0 4_665
O8 H8 O10 0.84 1.72 2.5040(17) 154.2 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.065
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_II
_database_code_depnum_ccdc_archive 'CCDC 1035033'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '2-oxo-1,2-dihydro-3-pyridinecarboxylic acid'
_chemical_name_common            2-ODHPCA
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 N O3'
_chemical_formula_sum            'C6 H5 N O3'
_chemical_formula_weight         139.11

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_space_group_name_Hall           '-P 2yn'

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                   3.725(1)
_cell_length_b                   7.368(2)
_cell_length_c                   20.417(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.47(1)
_cell_angle_gamma                90.00
_cell_volume                     560.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    1383
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       'thick needle'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9479
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2482
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         27.50
_reflns_number_total             1292
_reflns_number_gt                1014
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'

_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)+(0.0799P)²+0.0968P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1292
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.2287(4) 0.3893(2) 0.07618(7) 0.0156(4) Uani 1 1 d . . .
C3 C 0.0524(4) 0.3075(2) 0.13028(7) 0.0138(3) Uani 1 1 d . . .
C4 C 0.0055(4) 0.4065(2) 0.18654(7) 0.0156(4) Uani 1 1 d . . .
H4 H -0.1112 0.3521 0.2224 0.019 Uiso 1 1 calc R . .
C5 C 0.1263(4) 0.5859(2) 0.19194(7) 0.0165(4) Uani 1 1 d . . .
H5 H 0.0949 0.6528 0.2312 0.020 Uiso 1 1 calc R . .
C6 C 0.2902(4) 0.6627(2) 0.13968(8) 0.0166(4) Uani 1 1 d . . .
H6 H 0.3727 0.7846 0.1423 0.020 Uiso 1 1 calc R . .
C7 C -0.0778(4) 0.1165(2) 0.12578(7) 0.0159(4) Uani 1 1 d . . .
O10 O 0.2898(3) 0.30844(15) 0.02302(5) 0.0203(3) Uani 1 1 d . . .
N1 N 0.3354(3) 0.56572(17) 0.08429(6) 0.0157(3) Uani 1 1 d . . .
H1 H 0.4401 0.6195 0.0514 0.019 Uiso 1 1 calc R . .
O8 O -0.0119(3) 0.02815(15) 0.07075(5) 0.0203(3) Uani 1 1 d . . .
H8 H 0.1032 0.0958 0.0457 0.030 Uiso 1 1 calc R . .
O9 O -0.2376(3) 0.04360(15) 0.16969(5) 0.0209(3) Uani 1 1 d . . .

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
C2 0.0161(8) 0.0146(7) 0.0161(8) 0.0008(6) 0.0000(6) 0.0011(6)
C3 0.0130(7) 0.0130(7) 0.0153(8) 0.0010(6) -0.0001(6) 0.0009(6)
C4 0.0131(7) 0.0173(8) 0.0167(8) 0.0032(6) 0.0017(6) 0.0007(6)
C5 0.0162(8) 0.0172(8) 0.0161(7) -0.0029(6) 0.0005(6) 0.0026(6)
C6 0.0171(8) 0.0122(7) 0.0202(8) -0.0009(6) -0.0023(6) 0.0007(6)
C7 0.0160(7) 0.0160(8) 0.0155(7) 0.0003(6) 0.0005(6) 0.0008(6)
O10 0.0296(7) 0.0163(6) 0.0154(6) -0.0019(4) 0.0056(4) -0.0036(5)
N1 0.0171(7) 0.0146(7) 0.0155(7) 0.0015(5) 0.0024(5) -0.0009(5)
O8 0.0293(7) 0.0150(6) 0.0169(6) -0.0014(4) 0.0053(5) -0.0054(5)
O9 0.0257(6) 0.0169(6) 0.0204(6) 0.0004(4) 0.0061(5) -0.0030(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
C2 O10 1.2639(18) . ?
C2 N1 1.368(2) . ?
C2 C3 1.432(2) . ?
C3 C4 1.376(2) . ?
C3 C7 1.491(2) . ?
C4 C5 1.400(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.366(2) . ?
C5 H5 0.9500 . ?
C6 N1 1.352(2) . ?
C6 H6 0.9500 . ?
C7 O9 1.2142(18) . ?
C7 O8 1.3268(18) . ?
N1 H1 0.8800 . ?
O8 H8 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
O10 C2 N1 119.59(13) . . ?
O10 C2 C3 124.05(14) . . ?
N1 C2 C3 116.36(13) . . ?
C4 C3 C2 119.43(14) . . ?
C4 C3 C7 120.27(13) . . ?
C2 C3 C7 120.30(13) . . ?
C3 C4 C5 121.27(13) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 118.63(14) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
N1 C6 C5 120.14(14) . . ?
N1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O9 C7 O8 120.87(14) . . ?
O9 C7 C3 122.48(13) . . ?
O8 C7 C3 116.65(12) . . ?
C6 N1 C2 124.17(13) . . ?
C6 N1 H1 117.9 . . ?
C2 N1 H1 117.9 . . ?
C7 O8 H8 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
O10 C2 C3 C4 178.71(13) . . . . ?
N1 C2 C3 C4 -1.0(2) . . . . ?
O10 C2 C3 C7 -1.1(2) . . . . ?
N1 C2 C3 C7 179.22(12) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C7 C3 C4 C5 179.85(13) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 N1 -0.4(2) . . . . ?
C4 C3 C7 O9 2.4(2) . . . . ?
C2 C3 C7 O9 -177.83(14) . . . . ?
C4 C3 C7 O8 -177.84(13) . . . . ?
C2 C3 C7 O8 1.9(2) . . . . ?
C5 C6 N1 C2 -0.6(2) . . . . ?
O10 C2 N1 C6 -178.43(13) . . . . ?
C3 C2 N1 C6 1.3(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
N1 H1 O10 0.88 1.92 2.7869(17) 168.9 3_665
O8 H8 O10 0.84 1.78 2.5561(16) 152.8 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.070

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

data_III
_database_code_depnum_ccdc_archive 'CCDC 1035034'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '2-oxo-1,2-dihydro-3-pyridinecarboxylic acid'
_chemical_name_common            2-ODHPCA
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 N O3'
_chemical_formula_sum            'C6 H5 N O3'
_chemical_formula_weight         139.11

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   9.997(2)
_cell_length_b                   3.754(1)
_cell_length_c                   15.362(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.31(3)
_cell_angle_gamma                90.00
_cell_volume                     553.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(2)
_cell_measurement_reflns_used    1458
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.670
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9601
_exptl_absorpt_correction_T_max  0.9732
_exptl_absorpt_process_details   'Scalepack (Otwinowski & Minor, 1997)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω scans at fixed χ = 55°'
_diffrn_detector_area_resol_mean 18
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2322
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0298
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         27.49
_reflns_number_total             1263
_reflns_number_gt                991
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'COLLECT (Nonius, 2002)'
_computing_cell_refinement       'DENZO-SMN (Nonius, 1997)'
_computing_data_reduction        'DENZO-SMN (Nonius, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1995)'
_computing_publication_material  'SHELX-97 and local procedures'

_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)+(0.0611P)²+0.2405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1263
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.35224(14) 0.2723(4) 0.40230(10) 0.0157(3) Uani 1 1 d . . .
C3 C 0.24359(14) 0.4274(4) 0.33117(9) 0.0156(3) Uani 1 1 d . . .
C4 C 0.13334(15) 0.5926(4) 0.35085(10) 0.0170(3) Uani 1 1 d . . .
H4 H 0.0612 0.6923 0.3030 0.020 Uiso 1 1 calc R . .
C5 C 0.12520(15) 0.6173(4) 0.44013(10) 0.0189(4) Uani 1 1 d . . .
H5 H 0.0482 0.7308 0.4533 0.023 Uiso 1 1 calc R . .
C6 C 0.23038(15) 0.4747(4) 0.50780(10) 0.0186(4) Uani 1 1 d . . .
H6 H 0.2275 0.4917 0.5690 0.022 Uiso 1 1 calc R . .
C7 C 0.25236(15) 0.4153(4) 0.23561(10) 0.0179(4) Uani 1 1 d . . .
N1 N 0.33889(12) 0.3090(4) 0.48845(8) 0.0169(3) Uani 1 1 d . . .
H1 H 0.4048 0.2194 0.5338 0.020 Uiso 1 1 calc R . .
O8 O 0.36517(11) 0.2626(3) 0.22257(7) 0.0221(3) Uani 1 1 d . . .
H8 H 0.4179 0.1952 0.2726 0.033 Uiso 1 1 calc R . .
O9 O 0.16204(11) 0.5401(3) 0.17263(7) 0.0233(3) Uani 1 1 d . . .
O10 O 0.45649(10) 0.1097(3) 0.39036(7) 0.0196(3) Uani 1 1 d . . .

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
C2 0.0141(7) 0.0143(8) 0.0177(7) -0.0018(6) 0.0029(5) -0.0035(6)
C3 0.0157(7) 0.0140(8) 0.0162(7) 0.0001(6) 0.0031(6) -0.0031(6)
C4 0.0153(7) 0.0154(8) 0.0185(7) 0.0012(6) 0.0022(5) -0.0018(6)
C5 0.0163(7) 0.0181(8) 0.0220(8) -0.0009(6) 0.0052(6) 0.0005(6)
C6 0.0200(8) 0.0187(8) 0.0172(7) -0.0014(6) 0.0054(6) -0.0027(6)
C7 0.0161(7) 0.0190(8) 0.0176(7) -0.0005(6) 0.0031(6) -0.0041(6)
N1 0.0144(6) 0.0204(7) 0.0142(6) 0.0010(5) 0.0011(5) -0.0007(5)
O8 0.0186(6) 0.0316(7) 0.0162(5) 0.0006(5) 0.0048(4) 0.0011(5)
O9 0.0204(6) 0.0290(7) 0.0181(6) 0.0033(5) 0.0018(4) -0.0011(5)
O10 0.0162(5) 0.0245(6) 0.0174(5) 0.0005(5) 0.0033(4) 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
C2 O10 1.2648(18) . ?
C2 N1 1.3738(19) . ?
C2 C3 1.430(2) . ?
C3 C4 1.371(2) . ?
C3 C7 1.496(2) . ?
C4 C5 1.400(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.363(2) . ?
C5 H5 0.9500 . ?
C6 N1 1.3540(19) . ?
C6 H6 0.9500 . ?
C7 O9 1.2166(19) . ?
C7 O8 1.3294(19) . ?
N1 H1 0.8800 . ?
O8 H8 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
O10 C2 N1 119.67(13) . . ?
O10 C2 C3 124.43(13) . . ?
N1 C2 C3 115.90(13) . . ?
C4 C3 C2 120.06(13) . . ?
C4 C3 C7 120.17(13) . . ?
C2 C3 C7 119.75(13) . . ?
C3 C4 C5 121.18(14) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 118.46(14) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N1 C6 C5 120.45(14) . . ?
N1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O9 C7 O8 121.18(14) . . ?
O9 C7 C3 122.27(14) . . ?
O8 C7 C3 116.55(13) . . ?
C6 N1 C2 123.93(13) . . ?
C6 N1 H1 118.0 . . ?
C2 N1 H1 118.0 . . ?
C7 O8 H8 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
O10 C2 C3 C4 178.77(14) . . . . ?
N1 C2 C3 C4 -1.4(2) . . . . ?
O10 C2 C3 C7 -2.6(2) . . . . ?
N1 C2 C3 C7 177.25(13) . . . . ?
C2 C3 C4 C5 0.8(2) . . . . ?
C7 C3 C4 C5 -177.91(14) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 N1 -0.9(2) . . . . ?
C4 C3 C7 O9 -2.1(2) . . . . ?
C2 C3 C7 O9 179.24(14) . . . . ?
C4 C3 C7 O8 177.43(14) . . . . ?
C2 C3 C7 O8 -1.2(2) . . . . ?
C5 C6 N1 C2 0.2(2) . . . . ?
O10 C2 N1 C6 -179.21(14) . . . . ?
C3 C2 N1 C6 1.0(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
N1 H1 O10 0.88 1.97 2.8253(18) 162.1 3_656
O8 H8 O10 0.84 1.77 2.5466(16) 153.0 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.063
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IV
_database_code_depnum_ccdc_archive 'CCDC 1035035'
_audit_update_record             
;
2014-11-19 deposited with the CCDC.
2015-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        '2-oxo-1,2-dihydro-3-pyridinecarboxylic acid'
_chemical_name_common            2-ODHPCA
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H5 N O3'
_chemical_formula_sum            'C6 H5 N O3'
_chemical_formula_weight         556.44

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

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   'P 21/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                   9.773(2)
_cell_length_b                   4.0520(8)
_cell_length_c                   14.993(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.95(3)
_cell_angle_gamma                90.00
_cell_volume                     558.1(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       'long block, needle'
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8877
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2298
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0425
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.52
_reflns_number_total             1277
_reflns_number_gt                1067
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0653P)²+0.1691P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1277
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O8 O 0.14592(10) 0.4661(3) 0.30288(6) 0.0214(3) Uani 1 1 d . . .
H8 H 0.0946 0.5936 0.3225 0.032 Uiso 1 1 calc R . .
O9 O 0.34208(10) 0.1547(3) 0.36515(6) 0.0242(3) Uani 1 1 d . . .
O10 O 0.05249(9) 0.8099(3) 0.41393(6) 0.0193(3) Uani 1 1 d . . .
N1 N 0.16055(11) 0.7493(3) 0.57373(7) 0.0169(3) Uani 1 1 d . . .
H1 H 0.0951 0.8838 0.5819 0.020 Uiso 1 1 calc R . .
C2 C 0.15264(14) 0.6801(3) 0.48294(9) 0.0167(3) Uani 1 1 d . . .
C3 C 0.26049(13) 0.4586(3) 0.47288(8) 0.0164(3) Uani 1 1 d . . .
C4 C 0.36702(14) 0.3385(3) 0.55211(9) 0.0180(3) Uani 1 1 d . . .
H4 H 0.4404 0.1981 0.5450 0.022 Uiso 1 1 calc R . .
C5 C 0.36878(14) 0.4208(4) 0.64376(9) 0.0190(3) Uani 1 1 d . . .
H5 H 0.4422 0.3364 0.6985 0.023 Uiso 1 1 calc R . .
C6 C 0.26297(14) 0.6240(3) 0.65213(9) 0.0185(3) Uani 1 1 d . . .
H6 H 0.2608 0.6783 0.7133 0.022 Uiso 1 1 calc R . .
C7 C 0.25449(14) 0.3472(4) 0.37658(9) 0.0182(3) Uani 1 1 d . . .

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
O8 0.0245(5) 0.0259(6) 0.0135(4) -0.0001(4) 0.0061(4) 0.0015(4)
O9 0.0248(5) 0.0298(6) 0.0193(5) -0.0033(4) 0.0092(4) 0.0015(4)
O10 0.0180(5) 0.0240(5) 0.0144(5) 0.0018(4) 0.0036(4) 0.0012(4)
N1 0.0179(5) 0.0194(6) 0.0141(5) -0.0002(5) 0.0065(4) 0.0001(5)
C2 0.0173(6) 0.0184(7) 0.0141(6) 0.0006(5) 0.0049(5) -0.0048(5)
C3 0.0183(6) 0.0178(7) 0.0140(6) -0.0001(5) 0.0066(5) -0.0032(5)
C4 0.0179(6) 0.0172(7) 0.0190(6) -0.0013(5) 0.0065(5) -0.0022(5)
C5 0.0198(6) 0.0197(7) 0.0146(6) 0.0016(5) 0.0022(5) -0.0011(5)
C6 0.0214(6) 0.0206(7) 0.0120(6) -0.0002(5) 0.0040(5) -0.0041(5)
C7 0.0194(6) 0.0204(7) 0.0156(6) -0.0012(5) 0.0070(5) -0.0035(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
O8 C7 1.3338(16) . ?
O8 H8 0.8400 . ?
O9 C7 1.2129(17) . ?
O10 C2 1.2704(16) . ?
N1 C6 1.3561(17) . ?
N1 C2 1.3660(17) . ?
N1 H1 0.8800 . ?
C2 C3 1.4310(19) . ?
C3 C4 1.3741(19) . ?
C3 C7 1.4946(18) . ?
C4 C5 1.4083(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.361(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O8 H8 109.5 . . ?
C6 N1 C2 124.12(12) . . ?
C6 N1 H1 117.9 . . ?
C2 N1 H1 117.9 . . ?
O10 C2 N1 119.50(12) . . ?
O10 C2 C3 124.36(12) . . ?
N1 C2 C3 116.14(12) . . ?
C4 C3 C2 119.94(12) . . ?
C4 C3 C7 119.78(12) . . ?
C2 C3 C7 120.24(12) . . ?
C3 C4 C5 120.87(13) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.47(12) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N1 C6 C5 120.41(12) . . ?
N1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O9 C7 O8 121.03(12) . . ?
O9 C7 C3 122.27(12) . . ?
O8 C7 C3 116.69(12) . . ?

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 O10 -179.99(12) . . . . ?
C6 N1 C2 C3 0.46(19) . . . . ?
O10 C2 C3 C4 178.14(13) . . . . ?
N1 C2 C3 C4 -2.33(19) . . . . ?
O10 C2 C3 C7 -4.2(2) . . . . ?
N1 C2 C3 C7 175.36(12) . . . . ?
C2 C3 C4 C5 2.3(2) . . . . ?
C7 C3 C4 C5 -175.36(12) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C2 N1 C6 C5 1.5(2) . . . . ?
C4 C5 C6 N1 -1.5(2) . . . . ?
C4 C3 C7 O9 -0.8(2) . . . . ?
C2 C3 C7 O9 -178.51(13) . . . . ?
C4 C3 C7 O8 178.15(11) . . . . ?
C2 C3 C7 O8 0.46(19) . . . . ?

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
N1 H1 O10 0.88 1.92 2.7966(16) 174.1 3_576

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.053
