# 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_Salt1
_database_code_depnum_ccdc_archive 'CCDC 1417575'
_audit_update_record             
;
2015-08-08 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O, Cl, H2 O'
_chemical_formula_sum            'C10 H11 Cl N2 O2'
_chemical_formula_weight         226.66

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'
Cl Cl 0.1484 0.1585 '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                   7.650(9)
_cell_length_b                   7.943(8)
_cell_length_c                   18.15(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.26(2)
_cell_angle_gamma                90.00
_cell_volume                     1102(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   multi-Scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2011
_diffrn_reflns_av_R_equivalents  0.0946
_diffrn_reflns_av_sigmaI/netI    0.1632
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         6.25
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1975
_reflns_number_gt                1250
_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)+(0.0000P)²+0.0200P] 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         1975
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.0787
_refine_ls_wR_factor_gt          0.0671
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.0321(7) 0.5695(4) 0.0975(2) 0.070(2) Uani 1 1 d . . .
H1 H 0.0119 0.6328 0.1318 0.104 Uiso 1 1 d R . .
N2 N 0.3669(9) -0.1450(5) 0.1308(4) 0.058(2) Uani 1 1 d . . .
H2B H 0.4062 -0.2423 0.1440 0.070 Uiso 1 1 d R . .
N1 N 0.0999(10) 0.4176(5) 0.1240(3) 0.060(3) Uani 1 1 d . . .
C4 C 0.3514(12) -0.0273(7) 0.1808(4) 0.051(3) Uani 1 1 d . . .
H4 H 0.3882 -0.0477 0.2295 0.062 Uiso 1 1 calc R . .
C3 C 0.2805(12) 0.1264(6) 0.1613(4) 0.059(3) Uani 1 1 d . . .
H3 H 0.2667 0.2077 0.1975 0.071 Uiso 1 1 calc R . .
C2 C 0.2302(12) 0.1623(6) 0.0903(4) 0.051(3) Uani 1 1 d . . .
C9 C 0.2522(12) 0.0360(6) 0.0351(4) 0.050(3) Uani 1 1 d . . .
C8 C 0.2094(13) 0.0554(8) -0.0409(4) 0.073(4) Uani 1 1 d . . .
H8 H 0.1658 0.1578 -0.0583 0.088 Uiso 1 1 calc R . .
C7 C 0.2310(14) -0.0731(9) -0.0887(4) 0.072(4) Uani 1 1 d . . .
H7 H 0.1951 -0.0601 -0.1380 0.086 Uiso 1 1 calc R . .
C6 C 0.3062(16) -0.2243(9) -0.0651(5) 0.088(4) Uani 1 1 d . . .
H6 H 0.3276 -0.3082 -0.0994 0.105 Uiso 1 1 calc R . .
C5 C 0.3483(13) -0.2505(7) 0.0069(5) 0.071(3) Uani 1 1 d . . .
H5 H 0.3917 -0.3542 0.0229 0.085 Uiso 1 1 calc R . .
C10 C 0.3257(12) -0.1194(6) 0.0570(5) 0.057(3) Uani 1 1 d . . .
C1 C 0.1547(13) 0.3258(7) 0.0716(4) 0.060(3) Uani 1 1 d . . .
H1A H 0.1464 0.3626 0.0229 0.072 Uiso 1 1 calc R . .
Cl1 Cl 0.5363(4) 0.54441(16) 0.19923(11) 0.0794(11) Uani 1 1 d . . .
O2 O 0.5991(12) 0.2130(9) 0.2884(3) 0.094(3) Uani 1 1 d . . .
H2A H 0.636(10) 0.325(7) 0.262(4) 0.08(2) Uiso 1 1 d . . .
H3A H 0.705(14) 0.154(6) 0.277(4) 0.05(2) Uiso 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
O1 0.073(8) 0.070(3) 0.064(3) 0.0012(19) -0.016(4) 0.014(2)
N2 0.060(8) 0.054(3) 0.060(5) 0.004(3) 0.002(5) 0.001(3)
N1 0.074(9) 0.052(3) 0.054(4) -0.003(2) -0.009(5) 0.003(3)
C4 0.043(10) 0.067(4) 0.043(5) 0.004(3) -0.013(5) 0.000(4)
C3 0.076(12) 0.055(3) 0.047(5) -0.008(3) 0.002(6) -0.001(3)
C2 0.054(11) 0.052(4) 0.048(5) 0.007(3) -0.002(6) -0.003(3)
C9 0.047(10) 0.053(3) 0.051(6) 0.000(3) 0.003(6) -0.009(3)
C8 0.094(13) 0.081(4) 0.045(6) -0.002(3) 0.009(6) -0.019(4)
C7 0.066(13) 0.100(5) 0.048(5) -0.017(4) -0.020(6) -0.003(5)
C6 0.116(13) 0.075(5) 0.075(7) -0.026(4) 0.037(8) -0.021(4)
C5 0.073(12) 0.064(4) 0.076(7) -0.002(4) 0.013(7) -0.008(3)
C10 0.058(11) 0.055(4) 0.059(6) -0.005(3) 0.011(6) -0.013(3)
C1 0.069(11) 0.061(4) 0.049(5) 0.002(3) -0.014(6) 0.003(4)
Cl1 0.086(3) 0.0608(9) 0.0907(15) 0.0025(8) -0.0108(15) 0.0087(10)
O2 0.081(9) 0.102(4) 0.100(5) 0.040(3) -0.008(5) 0.007(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
O1 N1 1.391(6) . ?
O1 H1 0.8199 . ?
N2 C4 1.313(7) . ?
N2 C10 1.377(9) . ?
N2 H2B 0.8600 . ?
N1 C1 1.283(8) . ?
C4 C3 1.376(8) . ?
C4 H4 0.9300 . ?
C3 C2 1.360(9) . ?
C3 H3 0.9300 . ?
C2 C9 1.432(9) . ?
C2 C1 1.456(8) . ?
C9 C10 1.407(9) . ?
C9 C8 1.414(9) . ?
C8 C7 1.354(8) . ?
C8 H8 0.9300 . ?
C7 C6 1.392(11) . ?
C7 H7 0.9300 . ?
C6 C5 1.350(11) . ?
C6 H6 0.9300 . ?
C5 C10 1.399(9) . ?
C5 H5 0.9300 . ?
C1 H1A 0.9300 . ?
O2 H2A 1.05(7) . ?
O2 H3A 0.96(8) . ?

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
N1 O1 H1 110.4 . . ?
C4 N2 C10 123.0(5) . . ?
C4 N2 H2B 119.1 . . ?
C10 N2 H2B 117.9 . . ?
C1 N1 O1 111.4(5) . . ?
N2 C4 C3 119.9(6) . . ?
N2 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C2 C3 C4 121.6(6) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C3 C2 C9 118.6(5) . . ?
C3 C2 C1 120.2(6) . . ?
C9 C2 C1 121.2(7) . . ?
C10 C9 C8 116.5(6) . . ?
C10 C9 C2 118.3(7) . . ?
C8 C9 C2 125.3(6) . . ?
C7 C8 C9 121.0(7) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C8 C7 C6 120.8(8) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C5 C6 C7 120.7(7) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C5 C10 119.0(7) . . ?
C6 C5 H5 120.5 . . ?
C10 C5 H5 120.5 . . ?
N2 C10 C5 119.5(7) . . ?
N2 C10 C9 118.5(6) . . ?
C5 C10 C9 121.9(9) . . ?
N1 C1 C2 118.1(6) . . ?
N1 C1 H1A 120.9 . . ?
C2 C1 H1A 120.9 . . ?
H2A O2 H3A 94(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N2 C4 C3 4.4(11) . . . . ?
N2 C4 C3 C2 -2.0(11) . . . . ?
C4 C3 C2 C9 0.0(12) . . . . ?
C4 C3 C2 C1 179.6(6) . . . . ?
C3 C2 C9 C10 -0.2(11) . . . . ?
C1 C2 C9 C10 -179.9(7) . . . . ?
C3 C2 C9 C8 -178.8(8) . . . . ?
C1 C2 C9 C8 1.6(11) . . . . ?
C10 C9 C8 C7 3.1(11) . . . . ?
C2 C9 C8 C7 -178.3(8) . . . . ?
C9 C8 C7 C6 -4.1(12) . . . . ?
C8 C7 C6 C5 4.6(13) . . . . ?
C7 C6 C5 C10 -4.1(13) . . . . ?
C4 N2 C10 C5 179.0(7) . . . . ?
C4 N2 C10 C9 -4.6(11) . . . . ?
C6 C5 C10 N2 179.5(9) . . . . ?
C6 C5 C10 C9 3.3(12) . . . . ?
C8 C9 C10 N2 -178.9(8) . . . . ?
C2 C9 C10 N2 2.4(10) . . . . ?
C8 C9 C10 C5 -2.7(10) . . . . ?
C2 C9 C10 C5 178.6(8) . . . . ?
O1 N1 C1 C2 179.8(6) . . . . ?
C3 C2 C1 N1 -16.0(11) . . . . ?
C9 C2 C1 N1 163.7(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.099
_refine_diff_density_min         -0.102
_refine_diff_density_rms         0.023
####################################################################### 
# 
# 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_Salt2
_database_code_depnum_ccdc_archive 'CCDC 1417576'
_audit_update_record             
;
2015-08-08 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O, N O3'
_chemical_formula_sum            'C10 H9 N3 O4'
_chemical_formula_weight         235.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9402(7)
_cell_length_b                   8.1717(8)
_cell_length_c                   8.8975(8)
_cell_angle_alpha                70.343(6)
_cell_angle_beta                 89.333(6)
_cell_angle_gamma                72.343(6)
_cell_volume                     515.42(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   multi-Scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5360
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1864
_reflns_number_gt                1097
_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)+(0.1200P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1864
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1109
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_restrained_S_all      0.870
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.26430(17) 0.61020(17) 0.08803(14) 0.0608(5) Uani 1 1 d . . .
H1 H -0.3721 0.6338 0.0733 0.091 Uiso 1 1 calc R . .
N2 N 0.21162(19) -0.01634(18) 0.68731(14) 0.0441(5) Uani 1 1 d . . .
H2 H 0.2604 -0.1007 0.7772 0.053 Uiso 1 1 calc R . .
N1 N -0.2020(2) 0.47951(18) 0.23956(16) 0.0473(5) Uani 1 1 d . . .
C4 C 0.0799(2) 0.1275(2) 0.6896(2) 0.0460(5) Uani 1 1 d . . .
H4 H 0.0428 0.1354 0.7872 0.055 Uiso 1 1 calc R . .
C3 C -0.0030(2) 0.2657(2) 0.5486(2) 0.0446(5) Uani 1 1 d . . .
H3 H -0.0966 0.3655 0.5517 0.053 Uiso 1 1 calc R . .
C2 C 0.0519(2) 0.2574(2) 0.40253(19) 0.0379(5) Uani 1 1 d . . .
C8 C 0.2628(2) 0.0762(2) 0.2593(2) 0.0459(5) Uani 1 1 d . . .
H8 H 0.2147 0.1655 0.1599 0.055 Uiso 1 1 calc R . .
C7 C 0.3963(3) -0.0774(2) 0.2677(2) 0.0524(6) Uani 1 1 d . . .
H7 H 0.4392 -0.0920 0.1738 0.063 Uiso 1 1 calc R . .
C6 C 0.4712(3) -0.2153(2) 0.4166(2) 0.0524(5) Uani 1 1 d . . .
H6 H 0.5621 -0.3202 0.4197 0.063 Uiso 1 1 calc R . .
C5 C 0.4120(2) -0.1965(2) 0.5556(2) 0.0465(5) Uani 1 1 d . . .
H5 H 0.4620 -0.2876 0.6536 0.056 Uiso 1 1 calc R . .
C10 C 0.2740(2) -0.0376(2) 0.54930(18) 0.0382(5) Uani 1 1 d . . .
C9 C 0.1959(2) 0.1017(2) 0.40091(17) 0.0362(5) Uani 1 1 d . . .
C1 C -0.0358(3) 0.4014(2) 0.2507(2) 0.0441(5) Uani 1 1 d . . .
H1A H 0.0291 0.4348 0.1644 0.053 Uiso 1 1 calc R . .
O3 O 0.3079(2) 0.57795(18) 0.20573(14) 0.0652(5) Uani 1 1 d . . .
O4 O 0.38527(16) 0.73096(17) -0.01894(13) 0.0553(4) Uani 1 1 d . . .
O2 O 0.10762(18) 0.77117(18) 0.01384(14) 0.0603(4) Uani 1 1 d . . .
N3 N 0.2645(2) 0.69144(19) 0.06949(17) 0.0458(5) 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
O1 0.0467(10) 0.0600(8) 0.0501(8) 0.0069(6) -0.0068(6) -0.0101(7)
N2 0.0448(10) 0.0493(9) 0.0313(8) -0.0019(7) -0.0022(7) -0.0185(8)
N1 0.0470(12) 0.0454(9) 0.0383(8) -0.0033(7) -0.0017(7) -0.0116(8)
C4 0.0469(13) 0.0562(11) 0.0374(10) -0.0167(8) 0.0054(8) -0.0196(10)
C3 0.0430(12) 0.0435(10) 0.0460(11) -0.0151(8) 0.0046(9) -0.0126(9)
C2 0.0372(11) 0.0396(9) 0.0368(10) -0.0076(7) -0.0005(8) -0.0183(8)
C8 0.0478(13) 0.0533(11) 0.0360(9) -0.0112(8) 0.0017(8) -0.0202(10)
C7 0.0509(14) 0.0640(13) 0.0524(12) -0.0306(10) 0.0104(10) -0.0212(11)
C6 0.0414(13) 0.0464(11) 0.0694(13) -0.0228(10) 0.0027(10) -0.0110(9)
C5 0.0409(12) 0.0385(10) 0.0515(11) -0.0035(8) -0.0050(9) -0.0143(9)
C10 0.0361(11) 0.0400(10) 0.0376(9) -0.0074(8) -0.0013(8) -0.0176(9)
C9 0.0357(11) 0.0378(9) 0.0346(9) -0.0076(7) -0.0007(7) -0.0166(8)
C1 0.0413(14) 0.0448(10) 0.0411(10) -0.0066(8) 0.0033(8) -0.0162(9)
O3 0.0753(12) 0.0609(9) 0.0374(8) 0.0017(7) -0.0037(7) -0.0118(8)
O4 0.0443(9) 0.0710(9) 0.0420(8) -0.0107(6) 0.0048(6) -0.0165(7)
O2 0.0394(10) 0.0753(9) 0.0510(8) -0.0146(7) -0.0006(7) -0.0051(8)
N3 0.0519(12) 0.0464(9) 0.0342(9) -0.0123(7) 0.0010(8) -0.0107(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
O1 N1 1.3890(17) . ?
O1 H1 0.8200 . ?
N2 C4 1.321(2) . ?
N2 C10 1.3640(19) . ?
N2 H2 0.8600 . ?
N1 C1 1.268(2) . ?
C4 C3 1.378(2) . ?
C4 H4 0.9300 . ?
C3 C2 1.383(2) . ?
C3 H3 0.9300 . ?
C2 C9 1.434(2) . ?
C2 C1 1.466(2) . ?
C8 C7 1.355(2) . ?
C8 C9 1.417(2) . ?
C8 H8 0.9300 . ?
C7 C6 1.409(2) . ?
C7 H7 0.9300 . ?
C6 C5 1.358(2) . ?
C6 H6 0.9300 . ?
C5 C10 1.407(2) . ?
C5 H5 0.9300 . ?
C10 C9 1.415(2) . ?
C1 H1A 0.9300 . ?
O3 N3 1.2278(18) . ?
O4 N3 1.2813(18) . ?
O2 N3 1.2357(18) . ?

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
N1 O1 H1 109.5 . . ?
C4 N2 C10 123.21(14) . . ?
C4 N2 H2 118.4 . . ?
C10 N2 H2 118.4 . . ?
C1 N1 O1 111.33(14) . . ?
N2 C4 C3 120.53(15) . . ?
N2 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C3 C2 120.53(16) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C2 C9 118.68(15) . . ?
C3 C2 C1 121.58(16) . . ?
C9 C2 C1 119.73(15) . . ?
C7 C8 C9 120.43(15) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C7 C6 121.04(16) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C5 C6 C7 120.62(16) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C5 C10 119.17(15) . . ?
C6 C5 H5 120.4 . . ?
C10 C5 H5 120.4 . . ?
N2 C10 C5 120.18(14) . . ?
N2 C10 C9 118.75(15) . . ?
C5 C10 C9 121.07(15) . . ?
C10 C9 C8 117.67(15) . . ?
C10 C9 C2 118.30(15) . . ?
C8 C9 C2 124.02(15) . . ?
N1 C1 C2 118.61(16) . . ?
N1 C1 H1A 120.7 . . ?
C2 C1 H1A 120.7 . . ?
O3 N3 O2 122.45(16) . . ?
O3 N3 O4 119.39(17) . . ?
O2 N3 O4 118.16(14) . . ?

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
C10 N2 C4 C3 0.3(3) . . . . ?
N2 C4 C3 C2 -0.9(3) . . . . ?
C4 C3 C2 C9 0.3(2) . . . . ?
C4 C3 C2 C1 179.10(15) . . . . ?
C9 C8 C7 C6 0.3(3) . . . . ?
C8 C7 C6 C5 -0.6(3) . . . . ?
C7 C6 C5 C10 0.2(3) . . . . ?
C4 N2 C10 C5 -178.43(16) . . . . ?
C4 N2 C10 C9 0.7(2) . . . . ?
C6 C5 C10 N2 179.55(14) . . . . ?
C6 C5 C10 C9 0.4(3) . . . . ?
N2 C10 C9 C8 -179.84(13) . . . . ?
C5 C10 C9 C8 -0.7(2) . . . . ?
N2 C10 C9 C2 -1.2(2) . . . . ?
C5 C10 C9 C2 177.93(14) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C7 C8 C9 C2 -178.17(15) . . . . ?
C3 C2 C9 C10 0.7(2) . . . . ?
C1 C2 C9 C10 -178.09(13) . . . . ?
C3 C2 C9 C8 179.23(13) . . . . ?
C1 C2 C9 C8 0.4(3) . . . . ?
O1 N1 C1 C2 -179.18(13) . . . . ?
C3 C2 C1 N1 -34.9(2) . . . . ?
C9 C2 C1 N1 143.82(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_Salt3
_database_code_depnum_ccdc_archive 'CCDC 1417577'
_audit_update_record             
;
2015-08-08 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O, 0.5(C2 O4)'
_chemical_formula_sum            'C11 H9 N2 O3'
_chemical_formula_weight         217.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.9838(2)
_cell_length_b                   9.8417(4)
_cell_length_c                   10.3031(5)
_cell_angle_alpha                100.059(3)
_cell_angle_beta                 100.517(3)
_cell_angle_gamma                91.372(3)
_cell_volume                     488.42(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             226
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   multi-Scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5830
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.25
_reflns_number_total             1706
_reflns_number_gt                1441
_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)+(0.1000P)²+0.0100P] 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         1706
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1339
_refine_ls_wR_factor_gt          0.1255
_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
C9 C 0.9550(3) 0.13923(14) 0.79114(13) 0.0361(4) Uani 1 1 d . . .
C10 C 1.1206(3) 0.17778(14) 0.70386(13) 0.0373(4) Uani 1 1 d . . .
C2 C 0.8188(3) 0.24444(14) 0.86417(13) 0.0371(4) Uani 1 1 d . . .
C3 C 0.8561(3) 0.37964(15) 0.84761(15) 0.0446(4) Uani 1 1 d . . .
H3 H 0.7699 0.4496 0.8945 0.054 Uiso 1 1 calc R . .
C5 C 1.2628(3) 0.07945(16) 0.63138(14) 0.0446(4) Uani 1 1 d . . .
H5 H 1.3705 0.1061 0.5743 0.054 Uiso 1 1 calc R . .
C8 C 0.9377(3) -0.00276(14) 0.80134(14) 0.0425(4) Uani 1 1 d . . .
H8 H 0.8306 -0.0319 0.8575 0.051 Uiso 1 1 calc R . .
C1 C 0.6409(3) 0.20890(14) 0.95341(14) 0.0401(4) Uani 1 1 d . . .
H1 H 0.5619 0.1198 0.9401 0.048 Uiso 1 1 calc R . .
C6 C 1.2420(3) -0.05590(16) 0.64528(16) 0.0483(4) Uani 1 1 d . . .
H6 H 1.3379 -0.1213 0.5985 0.058 Uiso 1 1 calc R . .
C4 C 1.0211(3) 0.41082(15) 0.76156(15) 0.0471(4) Uani 1 1 d . . .
H4 H 1.0462 0.5023 0.7522 0.056 Uiso 1 1 calc R . .
C7 C 1.0762(3) -0.09631(16) 0.72988(15) 0.0479(4) Uani 1 1 d . . .
H7 H 1.0609 -0.1889 0.7372 0.058 Uiso 1 1 calc R . .
C11 C 0.4779(3) 0.43139(14) 0.44865(14) 0.0419(4) Uani 1 1 d . . .
N2 N 1.1441(3) 0.31420(12) 0.69220(12) 0.0434(4) Uani 1 1 d . . .
H2 H 1.2420 0.3374 0.6381 0.052 Uiso 1 1 calc R . .
N1 N 0.5952(3) 0.30031(13) 1.04894(12) 0.0448(4) Uani 1 1 d . . .
O1 O 0.4178(2) 0.25029(11) 1.12003(11) 0.0517(4) Uani 1 1 d . . .
H1A H 0.4301 0.3012 1.1932 0.078 Uiso 1 1 calc R . .
O3 O 0.5382(3) 0.43443(10) 0.33712(11) 0.0613(4) Uani 1 1 d . . .
O2 O 0.3865(3) 0.32811(10) 0.48433(11) 0.0677(4) 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
C9 0.0369(8) 0.0400(8) 0.0326(7) 0.0099(6) 0.0073(6) -0.0047(6)
C10 0.0382(8) 0.0417(8) 0.0330(7) 0.0094(6) 0.0078(6) -0.0047(6)
C2 0.0370(8) 0.0438(8) 0.0318(7) 0.0089(6) 0.0087(6) -0.0057(6)
C3 0.0528(10) 0.0408(8) 0.0443(8) 0.0091(6) 0.0190(7) 0.0008(7)
C5 0.0447(9) 0.0551(9) 0.0368(8) 0.0085(7) 0.0147(6) -0.0002(7)
C8 0.0452(9) 0.0434(8) 0.0428(8) 0.0147(6) 0.0127(7) -0.0038(7)
C1 0.0445(9) 0.0410(8) 0.0375(7) 0.0092(6) 0.0141(6) -0.0046(6)
C6 0.0510(10) 0.0491(9) 0.0449(8) 0.0047(7) 0.0123(7) 0.0065(7)
C4 0.0569(10) 0.0391(8) 0.0505(9) 0.0133(7) 0.0197(7) -0.0028(7)
C7 0.0536(10) 0.0395(8) 0.0506(9) 0.0103(7) 0.0082(7) -0.0001(7)
C11 0.0539(9) 0.0386(8) 0.0404(8) 0.0126(6) 0.0226(6) 0.0002(6)
N2 0.0503(8) 0.0440(7) 0.0417(7) 0.0135(5) 0.0193(6) -0.0046(6)
N1 0.0499(8) 0.0500(7) 0.0410(7) 0.0135(6) 0.0212(6) -0.0044(6)
O1 0.0596(8) 0.0554(7) 0.0467(6) 0.0079(5) 0.0298(5) -0.0094(5)
O3 0.0992(10) 0.0479(7) 0.0449(6) 0.0040(5) 0.0411(6) -0.0111(6)
O2 0.1138(11) 0.0407(6) 0.0590(7) 0.0031(5) 0.0519(7) -0.0157(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
C9 C10 1.4176(19) . ?
C9 C8 1.4213(19) . ?
C9 C2 1.431(2) . ?
C10 N2 1.3729(17) . ?
C10 C5 1.404(2) . ?
C2 C3 1.3831(19) . ?
C2 C1 1.4658(19) . ?
C3 C4 1.380(2) . ?
C5 C6 1.368(2) . ?
C8 C7 1.358(2) . ?
C1 N1 1.2698(19) . ?
C6 C7 1.403(2) . ?
C4 N2 1.320(2) . ?
C11 O2 1.2433(15) . ?
C11 O3 1.2446(17) . ?
C11 C11 1.547(3) 2_666 ?
N1 O1 1.3792(15) . ?

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
C10 C9 C8 117.28(14) . . ?
C10 C9 C2 118.59(13) . . ?
C8 C9 C2 124.13(13) . . ?
N2 C10 C5 119.89(13) . . ?
N2 C10 C9 118.97(13) . . ?
C5 C10 C9 121.13(13) . . ?
C3 C2 C9 118.68(13) . . ?
C3 C2 C1 120.86(14) . . ?
C9 C2 C1 120.45(13) . . ?
C4 C3 C2 120.03(14) . . ?
C6 C5 C10 119.53(14) . . ?
C7 C8 C9 120.63(14) . . ?
N1 C1 C2 119.71(13) . . ?
C5 C6 C7 120.15(14) . . ?
N2 C4 C3 121.72(13) . . ?
C8 C7 C6 121.26(14) . . ?
O2 C11 O3 125.74(14) . . ?
O2 C11 C11 117.54(15) . 2_666 ?
O3 C11 C11 116.72(14) . 2_666 ?
C4 N2 C10 121.98(13) . . ?
C1 N1 O1 111.95(12) . . ?

_diffrn_measured_fraction_theta_max 0.969
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.969
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_Salt4
_database_code_depnum_ccdc_archive 'CCDC 1417578'
_audit_update_record             
;
2015-08-08 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N2 O, C4 H3 O4'
_chemical_formula_sum            'C14 H12 N2 O5'
_chemical_formula_weight         288.26

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           Triclinic
_symmetry_space_group_name_H-M   'P -1'
_space_group_name_Hall           '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.3961(7)
_cell_length_b                   9.4163(13)
_cell_length_c                   13.6395(17)
_cell_angle_alpha                75.670(9)
_cell_angle_beta                 89.392(9)
_cell_angle_gamma                80.448(8)
_cell_volume                     661.83(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   multi-Scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8617
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         25.25
_reflns_number_total             2322
_reflns_number_gt                1591
_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)+(0.0900P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2322
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0488
_refine_ls_wR_factor_ref         0.1469
_refine_ls_wR_factor_gt          0.1315
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
C9 C 0.4257(4) 0.7463(2) 0.85517(14) 0.0471(5) Uani 1 1 d . . .
C1 C 0.1196(4) 0.5861(2) 0.82480(16) 0.0577(6) Uani 1 1 d . . .
H1 H 0.1093 0.5465 0.8940 0.069 Uiso 1 1 calc R . .
C2 C 0.2867(4) 0.6926(2) 0.78754(14) 0.0497(5) Uani 1 1 d . . .
C3 C 0.3193(5) 0.7430(3) 0.68456(16) 0.0608(6) Uani 1 1 d . . .
H3 H 0.2337 0.7078 0.6392 0.073 Uiso 1 1 calc R . .
C10 C 0.5878(4) 0.8482(2) 0.81380(15) 0.0493(5) Uani 1 1 d . . .
C5 C 0.7329(5) 0.9037(3) 0.87656(17) 0.0613(6) Uani 1 1 d . . .
H5 H 0.8384 0.9708 0.8487 0.074 Uiso 1 1 calc R . .
C8 C 0.4118(4) 0.7043(2) 0.96207(15) 0.0562(6) Uani 1 1 d . . .
H8 H 0.3051 0.6388 0.9917 0.067 Uiso 1 1 calc R . .
C6 C 0.7152(5) 0.8569(3) 0.97880(17) 0.0682(7) Uani 1 1 d . . .
H6 H 0.8133 0.8909 1.0208 0.082 Uiso 1 1 calc R . .
C14 C 0.4306(4) 0.3322(2) 0.65905(15) 0.0521(6) Uani 1 1 d . . .
C11 C -0.0075(4) 0.1497(3) 0.62013(18) 0.0593(6) Uani 1 1 d . . .
C4 C 0.4746(5) 0.8431(3) 0.64866(16) 0.0622(6) Uani 1 1 d . . .
H4 H 0.4896 0.8767 0.5791 0.075 Uiso 1 1 calc R . .
C7 C 0.5529(5) 0.7587(3) 1.02212(17) 0.0663(7) Uani 1 1 d . . .
H7 H 0.5411 0.7304 1.0921 0.080 Uiso 1 1 calc R . .
C13 C 0.2819(4) 0.3425(3) 0.56565(15) 0.0603(6) Uani 1 1 d . . .
H13 H 0.3212 0.4118 0.5088 0.072 Uiso 1 1 calc R . .
C12 C 0.1040(5) 0.2696(3) 0.55023(16) 0.0659(7) Uani 1 1 d . . .
H12 H 0.0361 0.2977 0.4845 0.079 Uiso 1 1 calc R . .
N1 N -0.0119(4) 0.5475(2) 0.76253(13) 0.0580(5) Uani 1 1 d . . .
N2 N 0.6047(3) 0.89398(19) 0.71044(13) 0.0563(5) Uani 1 1 d . . .
H2 H 0.7017 0.9568 0.6854 0.068 Uiso 1 1 calc R . .
O4 O 0.4004(3) 0.23490(18) 0.74078(10) 0.0648(5) Uani 1 1 d . . .
H4A H 0.2845 0.1925 0.7321 0.097 Uiso 1 1 calc R . .
O3 O 0.0732(3) 0.10250(18) 0.71168(12) 0.0703(5) Uani 1 1 d . . .
O5 O 0.5813(3) 0.41746(18) 0.65442(12) 0.0687(5) Uani 1 1 d . . .
O2 O -0.1756(3) 0.1002(2) 0.58478(13) 0.0761(5) Uani 1 1 d . . .
O1 O -0.1587(3) 0.44576(19) 0.81034(11) 0.0704(5) Uani 1 1 d . . .
H1B H -0.2382 0.4220 0.7678 0.106 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
C9 0.0513(12) 0.0451(12) 0.0458(11) -0.0121(9) -0.0055(9) -0.0092(10)
C1 0.0673(15) 0.0580(14) 0.0506(12) -0.0128(10) -0.0112(11) -0.0190(12)
C2 0.0539(13) 0.0457(12) 0.0498(11) -0.0106(9) -0.0100(9) -0.0104(10)
C3 0.0748(16) 0.0603(14) 0.0511(12) -0.0138(10) -0.0117(11) -0.0217(12)
C10 0.0501(12) 0.0488(12) 0.0508(12) -0.0159(9) -0.0035(9) -0.0082(10)
C5 0.0596(14) 0.0624(14) 0.0681(14) -0.0195(12) -0.0011(11) -0.0226(11)
C8 0.0652(14) 0.0561(13) 0.0484(12) -0.0094(10) -0.0035(10) -0.0183(11)
C6 0.0741(17) 0.0772(17) 0.0634(15) -0.0283(13) -0.0135(13) -0.0241(14)
C14 0.0544(13) 0.0575(13) 0.0468(12) -0.0133(10) -0.0002(10) -0.0157(11)
C11 0.0491(13) 0.0622(14) 0.0719(15) -0.0214(12) 0.0052(11) -0.0178(12)
C4 0.0789(17) 0.0642(15) 0.0455(11) -0.0140(10) -0.0032(11) -0.0169(13)
C7 0.0840(17) 0.0719(16) 0.0485(12) -0.0178(11) -0.0074(12) -0.0235(14)
C13 0.0617(15) 0.0749(16) 0.0437(11) -0.0012(10) -0.0035(10) -0.0301(13)
C12 0.0633(15) 0.0868(17) 0.0490(12) -0.0036(11) -0.0073(11) -0.0362(14)
N1 0.0594(12) 0.0590(11) 0.0607(11) -0.0181(9) -0.0029(9) -0.0190(10)
N2 0.0604(11) 0.0556(11) 0.0539(10) -0.0106(8) 0.0037(9) -0.0171(9)
O4 0.0741(12) 0.0765(11) 0.0451(8) -0.0077(8) -0.0063(7) -0.0268(9)
O3 0.0709(11) 0.0712(11) 0.0647(10) 0.0013(8) 0.0017(8) -0.0280(9)
O5 0.0727(11) 0.0748(11) 0.0686(10) -0.0215(8) -0.0053(8) -0.0352(9)
O2 0.0666(11) 0.0859(12) 0.0901(12) -0.0319(10) 0.0043(9) -0.0384(9)
O1 0.0740(11) 0.0785(11) 0.0681(10) -0.0196(9) -0.0046(9) -0.0373(9)

_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
C9 C10 1.416(3) . ?
C9 C8 1.418(3) . ?
C9 C2 1.429(3) . ?
C1 N1 1.268(3) . ?
C1 C2 1.454(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.363(3) . ?
C10 N2 1.375(3) . ?
C10 C5 1.411(3) . ?
C5 C6 1.362(3) . ?
C8 C7 1.365(3) . ?
C6 C7 1.399(3) . ?
C14 O5 1.225(3) . ?
C14 O4 1.284(2) . ?
C14 C13 1.487(3) . ?
C11 O2 1.238(3) . ?
C11 O3 1.272(3) . ?
C11 C12 1.492(3) . ?
C4 N2 1.325(3) . ?
C13 C12 1.316(3) . ?
N1 O1 1.379(2) . ?

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
C10 C9 C8 117.34(19) . . ?
C10 C9 C2 118.54(18) . . ?
C8 C9 C2 124.1(2) . . ?
N1 C1 C2 119.7(2) . . ?
C3 C2 C9 117.9(2) . . ?
C3 C2 C1 120.59(19) . . ?
C9 C2 C1 121.49(18) . . ?
C4 C3 C2 121.2(2) . . ?
N2 C10 C5 119.3(2) . . ?
N2 C10 C9 119.46(19) . . ?
C5 C10 C9 121.3(2) . . ?
C6 C5 C10 118.6(2) . . ?
C7 C8 C9 120.9(2) . . ?
C5 C6 C7 121.5(2) . . ?
O5 C14 O4 122.2(2) . . ?
O5 C14 C13 117.93(19) . . ?
O4 C14 C13 119.9(2) . . ?
O2 C11 O3 123.2(2) . . ?
O2 C11 C12 117.3(2) . . ?
O3 C11 C12 119.5(2) . . ?
N2 C4 C3 121.6(2) . . ?
C8 C7 C6 120.3(2) . . ?
C12 C13 C14 130.6(2) . . ?
C13 C12 C11 131.0(2) . . ?
C1 N1 O1 112.25(18) . . ?
C4 N2 C10 121.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_Cocrystal1
_database_code_depnum_ccdc_archive 'CCDC 1417579'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2 O, 0.5(C6 H10 O4)'
_chemical_formula_sum            'C13 H13 N2 O3'
_chemical_formula_weight         245.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   12.7021(5)
_cell_length_b                   5.0401(2)
_cell_length_c                   19.1216(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.951(3)
_cell_angle_gamma                90.00
_cell_volume                     1209.25(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   multi-Scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16596
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_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         1.80
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2151
_reflns_number_gt                1488
_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)+(0.0900P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2151
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1415
_refine_ls_wR_factor_gt          0.1249
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.12846(10) -0.2197(3) 0.43756(6) 0.0587(4) Uani 1 1 d . . .
H1A H -0.1790 -0.3225 0.4298 0.088 Uiso 1 1 d R . .
N1 N -0.13032(12) -0.0486(3) 0.38048(8) 0.0477(4) Uani 1 1 d . . .
N2 N -0.02753(11) 0.6721(3) 0.22414(7) 0.0471(4) Uani 1 1 d . . .
C1 C -0.05568(15) 0.1193(4) 0.38996(10) 0.0520(5) Uani 1 1 d . . .
H1 H -0.0079 0.1204 0.4321 0.062 Uiso 1 1 calc R . .
C2 C -0.04483(14) 0.3127(4) 0.33411(9) 0.0427(5) Uani 1 1 d . . .
C3 C -0.12068(14) 0.3285(4) 0.27442(9) 0.0472(5) Uani 1 1 d . . .
H3 H -0.1795 0.2164 0.2694 0.057 Uiso 1 1 calc R . .
C4 C -0.10966(15) 0.5116(4) 0.22169(10) 0.0489(5) Uani 1 1 d . . .
H4 H -0.1632 0.5211 0.1826 0.059 Uiso 1 1 calc R . .
C5 C 0.13793(15) 0.8384(4) 0.28449(11) 0.0613(6) Uani 1 1 d . . .
H5 H 0.1429 0.9488 0.2462 0.074 Uiso 1 1 calc R . .
C6 C 0.21486(18) 0.8447(5) 0.34248(14) 0.0803(8) Uani 1 1 d . . .
H6 H 0.2729 0.9579 0.3436 0.096 Uiso 1 1 calc R . .
C7 C 0.20684(18) 0.6812(5) 0.40050(13) 0.0853(9) Uani 1 1 d . . .
H7 H 0.2584 0.6928 0.4406 0.102 Uiso 1 1 calc R . .
C8 C 0.12531(17) 0.5056(4) 0.39959(12) 0.0642(7) Uani 1 1 d . . .
H8 H 0.1230 0.3953 0.4383 0.077 Uiso 1 1 calc R . .
C9 C 0.04357(13) 0.4898(4) 0.33975(10) 0.0448(5) Uani 1 1 d . . .
C10 C 0.05074(14) 0.6647(4) 0.28249(9) 0.0435(5) Uani 1 1 d . . .
O3 O 0.51894(10) 0.5075(3) 0.37525(7) 0.0589(5) Uani 1 1 d . . .
H3A H 0.5273 0.4077 0.3427 0.088 Uiso 1 1 d R . .
O2 O 0.69544(10) 0.4828(3) 0.39777(8) 0.0571(4) Uani 1 1 d . . .
C11 C 0.61063(14) 0.5791(4) 0.40853(9) 0.0445(5) Uani 1 1 d . . .
C12 C 0.60787(14) 0.7953(4) 0.46286(9) 0.0486(5) Uani 1 1 d . . .
H12A H 0.6504 0.9431 0.4506 0.058 Uiso 1 1 calc R . .
H12B H 0.6415 0.7286 0.5085 0.058 Uiso 1 1 calc R . .
C13 C 0.49830(13) 0.8988(4) 0.47062(9) 0.0455(5) Uani 1 1 d . . .
H13A H 0.4661 0.9790 0.4263 0.055 Uiso 1 1 calc R . .
H13B H 0.4537 0.7511 0.4802 0.055 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
O1 0.0595(8) 0.0623(10) 0.0531(8) 0.0186(7) 0.0053(6) -0.0129(7)
N1 0.0518(9) 0.0457(10) 0.0463(9) 0.0084(8) 0.0099(7) 0.0006(8)
N2 0.0502(9) 0.0455(11) 0.0450(9) 0.0073(7) 0.0063(7) 0.0025(8)
C1 0.0491(10) 0.0597(14) 0.0444(11) 0.0134(10) -0.0016(8) -0.0059(10)
C2 0.0432(9) 0.0422(11) 0.0427(10) 0.0028(9) 0.0065(7) 0.0005(8)
C3 0.0491(10) 0.0468(12) 0.0443(10) 0.0058(9) 0.0028(8) -0.0059(9)
C4 0.0512(11) 0.0508(13) 0.0423(11) 0.0042(9) -0.0001(8) 0.0018(9)
C5 0.0562(12) 0.0552(15) 0.0722(14) 0.0178(11) 0.0094(10) -0.0072(10)
C6 0.0586(13) 0.0719(17) 0.1034(19) 0.0249(15) -0.0099(12) -0.0219(12)
C7 0.0669(15) 0.0852(19) 0.0908(18) 0.0294(16) -0.0281(12) -0.0241(14)
C8 0.0573(12) 0.0645(16) 0.0644(14) 0.0204(11) -0.0108(10) -0.0106(11)
C9 0.0440(10) 0.0431(12) 0.0457(11) 0.0063(9) 0.0023(8) 0.0033(8)
C10 0.0448(9) 0.0393(12) 0.0461(10) 0.0061(9) 0.0058(8) 0.0043(8)
O3 0.0530(8) 0.0660(11) 0.0572(9) -0.0284(7) 0.0066(6) -0.0040(6)
O2 0.0514(8) 0.0517(10) 0.0693(9) -0.0170(7) 0.0129(7) 0.0015(6)
C11 0.0481(10) 0.0427(12) 0.0432(10) -0.0042(9) 0.0088(8) -0.0025(9)
C12 0.0485(10) 0.0488(12) 0.0480(10) -0.0116(9) 0.0061(8) -0.0037(9)
C13 0.0452(10) 0.0474(12) 0.0432(10) -0.0095(9) 0.0049(8) -0.0043(9)

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.3884(19) . ?
O1 H1A 0.8200 . ?
N1 C1 1.263(2) . ?
N2 C4 1.315(2) . ?
N2 C10 1.375(2) . ?
C1 C2 1.468(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.377(2) . ?
C2 C9 1.425(2) . ?
C3 C4 1.390(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.360(3) . ?
C5 C10 1.408(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.398(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.360(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.423(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.420(2) . ?
O3 C11 1.289(2) . ?
O3 H3A 0.8199 . ?
O2 C11 1.228(2) . ?
C11 C12 1.510(3) . ?
C12 C13 1.515(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C13 1.513(4) 3_676 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
N1 O1 H1A 109.5 . . ?
C1 N1 O1 112.51(15) . . ?
C4 N2 C10 118.80(15) . . ?
N1 C1 C2 119.59(16) . . ?
N1 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C3 C2 C9 117.90(16) . . ?
C3 C2 C1 120.59(16) . . ?
C9 C2 C1 121.51(15) . . ?
C2 C3 C4 120.24(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
N2 C4 C3 123.47(16) . . ?
N2 C4 H4 118.3 . . ?
C3 C4 H4 118.3 . . ?
C6 C5 C10 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C10 C5 H5 120.0 . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 121.50(19) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 117.32(17) . . ?
C10 C9 C2 118.35(16) . . ?
C8 C9 C2 124.33(17) . . ?
N2 C10 C5 118.16(16) . . ?
N2 C10 C9 121.17(16) . . ?
C5 C10 C9 120.66(17) . . ?
C11 O3 H3A 109.5 . . ?
O2 C11 O3 123.75(17) . . ?
O2 C11 C12 121.04(16) . . ?
O3 C11 C12 115.22(16) . . ?
C11 C12 C13 115.84(15) . . ?
C11 C12 H12A 108.3 . . ?
C13 C12 H12A 108.3 . . ?
C11 C12 H12B 108.3 . . ?
C13 C12 H12B 108.3 . . ?
H12A C12 H12B 107.4 . . ?
C13 C13 C12 112.59(18) 3_676 . ?
C13 C13 H13A 109.1 3_676 . ?
C12 C13 H13A 109.1 . . ?
C13 C13 H13B 109.1 3_676 . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 178.94(15) . . . . ?
N1 C1 C2 C3 6.0(3) . . . . ?
N1 C1 C2 C9 -174.22(17) . . . . ?
C9 C2 C3 C4 0.4(3) . . . . ?
C1 C2 C3 C4 -179.80(18) . . . . ?
C10 N2 C4 C3 -1.7(3) . . . . ?
C2 C3 C4 N2 1.8(3) . . . . ?
C10 C5 C6 C7 -0.8(4) . . . . ?
C5 C6 C7 C8 2.7(4) . . . . ?
C6 C7 C8 C9 -2.0(4) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C7 C8 C9 C2 -179.9(2) . . . . ?
C3 C2 C9 C10 -2.5(3) . . . . ?
C1 C2 C9 C10 177.73(17) . . . . ?
C3 C2 C9 C8 176.83(19) . . . . ?
C1 C2 C9 C8 -3.0(3) . . . . ?
C4 N2 C10 C5 -179.74(17) . . . . ?
C4 N2 C10 C9 -0.6(3) . . . . ?
C6 C5 C10 N2 177.4(2) . . . . ?
C6 C5 C10 C9 -1.8(3) . . . . ?
C8 C9 C10 N2 -176.71(18) . . . . ?
C2 C9 C10 N2 2.7(3) . . . . ?
C8 C9 C10 C5 2.4(3) . . . . ?
C2 C9 C10 C5 -178.21(17) . . . . ?
O2 C11 C12 C13 179.53(18) . . . . ?
O3 C11 C12 C13 -0.2(3) . . . . ?
C11 C12 C13 C13 176.12(19) . . . 3_676 ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_Cocrystal2
_database_code_depnum_ccdc_archive 'CCDC 1417580'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2 O, 0.5(C4 H6 O4)'
_chemical_formula_sum            'C12 H11 N2 O3'
_chemical_formula_weight         231.23

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                   12.7915(5)
_cell_length_b                   5.0009(2)
_cell_length_c                   16.4829(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.926(3)
_cell_angle_gamma                90.00
_cell_volume                     1054.26(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?


_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   multi-Scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10437
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0280
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1843
_reflns_number_gt                1341
_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)+(0.0900P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1843
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1408
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 -0.05598(14) 0.5972(4) 0.33104(11) 0.0345(5) Uani 1 1 d . . .
C9 C 0.03755(14) 0.4409(4) 0.33830(11) 0.0344(5) Uani 1 1 d . . .
C8 C 0.11384(15) 0.4696(4) 0.40088(12) 0.0427(6) Uani 1 1 d . . .
H8 H 0.1042 0.5987 0.4407 0.051 Uiso 1 1 calc R . .
C10 C 0.05564(13) 0.2417(4) 0.27875(11) 0.0341(5) Uani 1 1 d . . .
C3 C -0.12339(14) 0.5449(4) 0.26783(11) 0.0397(5) Uani 1 1 d . . .
H3 H -0.1844 0.6444 0.2617 0.048 Uiso 1 1 calc R . .
C1 C -0.07754(15) 0.8102(4) 0.39004(12) 0.0406(5) Uani 1 1 d . . .
H1 H -0.0294 0.8473 0.4314 0.049 Uiso 1 1 calc R . .
C4 C -0.10080(15) 0.3426(4) 0.21259(11) 0.0410(5) Uani 1 1 d . . .
H4 H -0.1487 0.3084 0.1708 0.049 Uiso 1 1 calc R . .
C5 C 0.14637(14) 0.0816(4) 0.28345(12) 0.0422(6) Uani 1 1 d . . .
H5 H 0.1577 -0.0486 0.2443 0.051 Uiso 1 1 calc R . .
C7 C 0.20092(15) 0.3132(4) 0.40434(13) 0.0475(6) Uani 1 1 d . . .
H7 H 0.2497 0.3364 0.4462 0.057 Uiso 1 1 calc R . .
C6 C 0.21740(15) 0.1166(5) 0.34490(13) 0.0481(6) Uani 1 1 d . . .
H6 H 0.2770 0.0102 0.3476 0.058 Uiso 1 1 calc R . .
C12 C 0.94744(14) 0.5576(4) 0.00580(12) 0.0439(6) Uani 1 1 d . . .
H12A H 0.9007 0.4132 0.0203 0.053 Uiso 1 1 calc R . .
H12B H 0.9230 0.6278 -0.0460 0.053 Uiso 1 1 calc R . .
C11 C 0.93688(15) 0.7748(4) 0.06797(12) 0.0391(5) Uani 1 1 d . . .
N2 N -0.01477(12) 0.1974(3) 0.21667(9) 0.0380(4) Uani 1 1 d . . .
N1 N -0.16185(12) 0.9432(4) 0.38452(9) 0.0398(5) Uani 1 1 d . . .
O3 O 1.02150(10) 0.8466(3) 0.10539(9) 0.0519(5) Uani 1 1 d . . .
H3A H 1.0071 0.9484 0.1426 0.078 Uiso 1 1 calc R . .
O1 O -0.16787(10) 1.1358(3) 0.44484(8) 0.0476(5) Uani 1 1 d . . .
H1A H -0.2244 1.2123 0.4414 0.071 Uiso 1 1 calc R . .
O2 O 0.85063(10) 0.8752(3) 0.08136(9) 0.0485(4) 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 0.0389(10) 0.0323(13) 0.0324(10) -0.0011(8) 0.0014(8) -0.0037(8)
C9 0.0377(10) 0.0334(13) 0.0322(10) 0.0000(9) -0.0003(8) -0.0014(8)
C8 0.0505(12) 0.0387(14) 0.0386(11) -0.0059(10) -0.0053(9) 0.0005(10)
C10 0.0375(10) 0.0315(12) 0.0334(10) -0.0021(9) 0.0019(8) -0.0040(8)
C3 0.0400(11) 0.0396(14) 0.0394(11) -0.0039(10) -0.0046(9) 0.0034(9)
C1 0.0424(11) 0.0434(14) 0.0357(11) -0.0049(9) -0.0046(9) 0.0036(9)
C4 0.0460(11) 0.0435(14) 0.0333(11) -0.0032(9) -0.0068(9) -0.0039(10)
C5 0.0422(11) 0.0366(14) 0.0479(13) -0.0042(10) 0.0052(9) 0.0025(9)
C7 0.0428(12) 0.0498(16) 0.0495(13) -0.0007(11) -0.0109(9) 0.0026(10)
C6 0.0418(11) 0.0461(15) 0.0562(14) 0.0038(11) -0.0021(10) 0.0057(10)
C12 0.0490(12) 0.0429(15) 0.0398(11) -0.0102(10) -0.0021(9) -0.0080(10)
C11 0.0421(11) 0.0376(13) 0.0378(11) -0.0031(9) 0.0005(9) -0.0082(9)
N2 0.0383(9) 0.0395(11) 0.0361(9) -0.0044(8) -0.0021(7) -0.0024(7)
N1 0.0436(10) 0.0379(12) 0.0379(10) -0.0077(8) 0.0005(7) 0.0004(8)
O3 0.0445(8) 0.0568(12) 0.0544(10) -0.0273(8) -0.0016(7) -0.0024(7)
O1 0.0501(9) 0.0455(10) 0.0471(9) -0.0177(7) -0.0029(7) 0.0112(7)
O2 0.0423(8) 0.0462(10) 0.0570(10) -0.0121(7) 0.0002(7) -0.0012(7)

_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 C3 1.367(2) . ?
C2 C9 1.432(3) . ?
C2 C1 1.472(3) . ?
C9 C8 1.416(3) . ?
C9 C10 1.420(3) . ?
C8 C7 1.362(3) . ?
C10 N2 1.370(2) . ?
C10 C5 1.411(3) . ?
C3 C4 1.395(3) . ?
C1 N1 1.269(2) . ?
C4 N2 1.319(2) . ?
C5 C6 1.361(3) . ?
C7 C6 1.406(3) . ?
C12 C12 1.478(4) 3_765 ?
C12 C11 1.501(3) . ?
C11 O2 1.235(2) . ?
C11 O3 1.288(2) . ?
N1 O1 1.387(2) . ?

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
C3 C2 C9 118.38(18) . . ?
C3 C2 C1 121.30(18) . . ?
C9 C2 C1 120.32(17) . . ?
C8 C9 C10 117.16(18) . . ?
C8 C9 C2 124.80(18) . . ?
C10 C9 C2 118.04(18) . . ?
C7 C8 C9 121.7(2) . . ?
N2 C10 C5 118.66(17) . . ?
N2 C10 C9 121.13(17) . . ?
C5 C10 C9 120.20(18) . . ?
C2 C3 C4 120.10(18) . . ?
N1 C1 C2 120.01(18) . . ?
N2 C4 C3 123.20(17) . . ?
C6 C5 C10 120.44(19) . . ?
C8 C7 C6 120.28(19) . . ?
C5 C6 C7 120.17(19) . . ?
C12 C12 C11 117.6(2) 3_765 . ?
O2 C11 O3 123.17(18) . . ?
O2 C11 C12 120.44(17) . . ?
O3 C11 C12 116.39(17) . . ?
C4 N2 C10 119.14(17) . . ?
C1 N1 O1 111.68(15) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_Cocrystal3
_database_code_depnum_ccdc_archive 'CCDC 1417581'
_audit_update_record             
;
2015-11-09 deposited with the CCDC.
2015-11-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2 O, 0.5(C4 H4 O4)'
_chemical_formula_sum            'C12 H10 N2 O3'
_chemical_formula_weight         230.22

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                   12.6838(12)
_cell_length_b                   5.0451(5)
_cell_length_c                   16.3375(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.201(7)
_cell_angle_gamma                90.00
_cell_volume                     1045.45(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   multi-Scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12263
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1892
_reflns_number_gt                1402
_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)+(0.0800P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1892
_refine_ls_number_parameters     156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1191
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 1.05598(14) 0.6019(4) 0.83043(11) 0.0344(5) Uani 1 1 d . . .
C10 C 0.94294(13) 0.2457(4) 0.77921(11) 0.0331(5) Uani 1 1 d . . .
C9 C 0.96223(14) 0.4451(3) 0.83875(11) 0.0327(4) Uani 1 1 d . . .
C3 C 1.12250(15) 0.5497(4) 0.76632(11) 0.0397(5) Uani 1 1 d . . .
H3 H 1.1840 0.6477 0.7600 0.048 Uiso 1 1 calc R . .
C8 C 0.88734(15) 0.4740(4) 0.90237(12) 0.0410(5) Uani 1 1 d . . .
H8 H 0.8980 0.6028 0.9423 0.049 Uiso 1 1 calc R . .
C1 C 1.07912(15) 0.8139(4) 0.88935(12) 0.0394(5) Uani 1 1 d . . .
H1 H 1.0317 0.8512 0.9311 0.047 Uiso 1 1 calc R . .
C5 C 0.85197(15) 0.0850(4) 0.78479(12) 0.0412(5) Uani 1 1 d . . .
H5 H 0.8396 -0.0452 0.7457 0.049 Uiso 1 1 calc R . .
C4 C 1.09765(15) 0.3492(4) 0.71065(12) 0.0399(5) Uani 1 1 d . . .
H4 H 1.1440 0.3165 0.6679 0.048 Uiso 1 1 calc R . .
C7 C 0.80005(16) 0.3172(4) 0.90636(13) 0.0454(5) Uani 1 1 d . . .
H7 H 0.7518 0.3406 0.9485 0.054 Uiso 1 1 calc R . .
C6 C 0.78255(16) 0.1198(4) 0.84694(13) 0.0462(5) Uani 1 1 d . . .
H6 H 0.7231 0.0125 0.8503 0.055 Uiso 1 1 calc R . .
C12 C 0.04449(15) 0.5611(4) 0.50808(12) 0.0411(5) Uani 1 1 d . . .
H12 H 0.1042 0.5073 0.4797 0.049 Uiso 1 1 calc R . .
C11 C 0.05691(15) 0.7800(4) 0.56879(12) 0.0373(5) Uani 1 1 d . . .
O1 O 1.17150(11) 1.1373(3) 0.94406(9) 0.0477(4) Uani 1 1 d . . .
H1A H 1.2273 1.2179 0.9394 0.071 Uiso 1 1 calc R . .
O3A O -0.02777(10) 0.8560(3) 0.60429(9) 0.0482(4) Uani 1 1 d . . .
H3A H -0.0135 0.9701 0.6383 0.072 Uiso 1 1 calc R . .
O2 O 0.14507(10) 0.8751(3) 0.58243(9) 0.0466(4) Uani 1 1 d . . .
N2 N 1.01148(12) 0.2039(3) 0.71585(10) 0.0371(4) Uani 1 1 d . . .
N1 N 1.16415(12) 0.9471(3) 0.88342(10) 0.0397(4) 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 0.0389(10) 0.0322(10) 0.0320(10) -0.0014(8) -0.0027(8) 0.0018(8)
C10 0.0357(10) 0.0317(10) 0.0318(11) -0.0012(8) -0.0008(8) 0.0036(8)
C9 0.0356(10) 0.0314(9) 0.0312(10) 0.0008(8) -0.0015(8) 0.0028(8)
C3 0.0390(11) 0.0412(11) 0.0389(12) -0.0028(9) 0.0034(9) -0.0034(9)
C8 0.0475(12) 0.0401(11) 0.0354(11) -0.0069(9) 0.0048(9) -0.0003(9)
C1 0.0414(11) 0.0414(11) 0.0355(11) -0.0055(9) 0.0031(9) -0.0045(9)
C5 0.0427(12) 0.0354(11) 0.0456(13) -0.0049(9) -0.0045(10) -0.0001(9)
C4 0.0446(12) 0.0415(11) 0.0336(11) -0.0020(9) 0.0061(9) 0.0026(9)
C7 0.0422(12) 0.0509(13) 0.0432(12) -0.0010(10) 0.0089(9) -0.0019(10)
C6 0.0400(11) 0.0455(12) 0.0530(14) 0.0038(10) 0.0023(10) -0.0078(9)
C12 0.0417(11) 0.0422(11) 0.0395(11) -0.0112(9) 0.0037(9) 0.0070(9)
C11 0.0405(11) 0.0368(11) 0.0344(11) -0.0044(8) -0.0014(9) 0.0073(9)
O1 0.0526(9) 0.0461(9) 0.0443(9) -0.0160(6) 0.0038(7) -0.0112(7)
O3A 0.0402(8) 0.0521(9) 0.0522(10) -0.0260(7) 0.0027(7) 0.0017(7)
O2 0.0396(8) 0.0453(8) 0.0548(9) -0.0126(7) -0.0007(7) 0.0013(6)
N2 0.0398(9) 0.0363(9) 0.0352(9) -0.0047(7) 0.0022(7) 0.0037(7)
N1 0.0446(10) 0.0365(9) 0.0381(10) -0.0079(7) -0.0016(8) -0.0015(7)

_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 C3 1.373(3) . ?
C2 C9 1.435(3) . ?
C2 C1 1.468(3) . ?
C10 N2 1.370(2) . ?
C10 C5 1.413(3) . ?
C10 C9 1.420(2) . ?
C9 C8 1.418(3) . ?
C3 C4 1.395(3) . ?
C8 C7 1.362(3) . ?
C1 N1 1.274(2) . ?
C5 C6 1.358(3) . ?
C4 N2 1.319(2) . ?
C7 C6 1.408(3) . ?
C12 C12 1.312(4) 3_566 ?
C12 C11 1.492(3) . ?
C11 O2 1.236(2) . ?
C11 O3A 1.281(2) . ?
O1 N1 1.3822(19) . ?

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
C3 C2 C9 118.57(17) . . ?
C3 C2 C1 121.20(18) . . ?
C9 C2 C1 120.23(17) . . ?
N2 C10 C5 118.74(16) . . ?
N2 C10 C9 121.20(16) . . ?
C5 C10 C9 120.06(17) . . ?
C8 C9 C10 117.42(17) . . ?
C8 C9 C2 124.78(17) . . ?
C10 C9 C2 117.81(17) . . ?
C2 C3 C4 119.88(18) . . ?
C7 C8 C9 121.47(18) . . ?
N1 C1 C2 120.10(18) . . ?
C6 C5 C10 120.40(18) . . ?
N2 C4 C3 123.10(18) . . ?
C8 C7 C6 120.25(19) . . ?
C5 C6 C7 120.39(19) . . ?
C12 C12 C11 124.8(2) 3_566 . ?
O2 C11 O3A 124.15(17) . . ?
O2 C11 C12 120.02(17) . . ?
O3A C11 C12 115.83(17) . . ?
C4 N2 C10 119.42(16) . . ?
C1 N1 O1 111.49(15) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.039
