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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_35dnba_ina

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 4-Carbamoylpyridinium 3,5-dinitrobenzoate
;
_chemical_name_common            
;
isonicotinamide - 3,5-dinitrobenzoic acid
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H3 N2 O6, C6 H7 N2 O'
_chemical_formula_sum            'C13 H10 N4 O7'
_chemical_formula_weight         334.25

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2376(6)
_cell_length_b                   8.9810(8)
_cell_length_c                   10.8011(8)
_cell_angle_alpha                87.807(7)
_cell_angle_beta                 76.086(7)
_cell_angle_gamma                87.040(7)
_cell_volume                     680.33(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2399
_cell_measurement_theta_min      3.0210
_cell_measurement_theta_max      28.3022

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.9
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78026
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;
'Enhance (Mo) X-ray Source' 
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3367
_diffrn_reflns_number            4505
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.029
_diffrn_reflns_theta_max         28.420
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2998
_reflns_number_gt                2223
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;

_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;

_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;

_computing_structure_solution    SHELXL97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0762P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2998
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   0.974
_refine_ls_restrained_S_all      0.974
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1B O 0.01317(18) -0.29674(13) -0.00420(11) 0.0186(3) Uani 1 1 d . . . . .
N2B N 0.1057(2) -0.45990(17) 0.13609(14) 0.0159(3) Uani 1 1 d . . . . .
H2BA H 0.068(3) -0.538(2) 0.0972(19) 0.023(5) Uiso 1 1 d . . . . .
H2BB H 0.152(3) -0.477(2) 0.206(2) 0.022(5) Uiso 1 1 d . . . . .
N1B N 0.2080(2) 0.04592(17) 0.28348(14) 0.0162(3) Uani 1 1 d . . . . .
H1B H 0.233(3) 0.131(3) 0.332(2) 0.042(7) Uiso 1 1 d . . . . .
C4B C 0.2108(3) 0.0588(2) 0.15904(16) 0.0177(4) Uani 1 1 d . . . . .
H4B H 0.248(3) 0.152(2) 0.1158(17) 0.016(5) Uiso 1 1 d . . . . .
C2B C 0.1267(2) -0.19452(18) 0.16159(16) 0.0140(4) Uani 1 1 d . . . . .
C6B C 0.1279(3) -0.2054(2) 0.29074(16) 0.0167(4) Uani 1 1 d . . . . .
H6B H 0.103(3) -0.293(2) 0.3375(18) 0.014(5) Uiso 1 1 d . . . . .
C3B C 0.1692(3) -0.06086(19) 0.09584(16) 0.0163(4) Uani 1 1 d . . . . .
H3B H 0.178(3) -0.053(2) 0.009(2) 0.029(6) Uiso 1 1 d . . . . .
C1B C 0.0783(2) -0.32343(19) 0.09124(15) 0.0143(4) Uani 1 1 d . . . . .
C5B C 0.1681(3) -0.08213(19) 0.34867(16) 0.0167(4) Uani 1 1 d . . . . .
H5B H 0.171(3) -0.081(2) 0.4376(19) 0.017(5) Uiso 1 1 d . . . . .
O6A O 0.40486(19) 0.14951(13) 0.85611(11) 0.0208(3) Uani 1 1 d . . . . .
O5A O 0.45327(19) 0.33536(14) 0.96455(11) 0.0210(3) Uani 1 1 d . . . . .
O2A O 0.19671(19) 0.45818(14) 0.37524(11) 0.0216(3) Uani 1 1 d . . . . .
O4A O 0.37945(19) 0.83612(14) 0.80247(12) 0.0229(3) Uani 1 1 d . . . . .
O1A O 0.2642(2) 0.22790(14) 0.44325(12) 0.0269(3) Uani 1 1 d . . . . .
O3A O 0.2269(2) 0.87348(14) 0.65318(13) 0.0271(3) Uani 1 1 d . . . . .
N1A N 0.3062(2) 0.79221(16) 0.72059(13) 0.0173(3) Uani 1 1 d . . . . .
N2A N 0.4125(2) 0.28292(16) 0.87170(13) 0.0155(3) Uani 1 1 d . . . . .
C4A C 0.3124(2) 0.63062(18) 0.70196(15) 0.0138(3) Uani 1 1 d . . . . .
C3A C 0.2668(2) 0.57865(19) 0.59450(16) 0.0147(4) Uani 1 1 d . . . . .
H3A H 0.231(3) 0.650(2) 0.5354(18) 0.015(5) Uiso 1 1 d . . . . .
C5A C 0.3659(2) 0.53740(19) 0.79325(16) 0.0143(4) Uani 1 1 d . . . . .
H5A H 0.399(3) 0.579(2) 0.868(2) 0.024(5) Uiso 1 1 d . . . . .
C6A C 0.3686(2) 0.38633(19) 0.77266(16) 0.0140(4) Uani 1 1 d . . . . .
C2A C 0.2790(2) 0.42617(19) 0.57446(15) 0.0146(4) Uani 1 1 d . . . . .
C1A C 0.2420(2) 0.36744(19) 0.45327(16) 0.0156(4) Uani 1 1 d . . . . .
C7A C 0.3292(2) 0.32875(19) 0.66544(16) 0.0144(4) Uani 1 1 d . . . . .
H7A H 0.339(3) 0.226(2) 0.6541(17) 0.014(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1B C1B 1.2431(19) . ?
N2B C1B 1.324(2) . ?
N2B H2BA 0.92(2) . ?
N2B H2BB 0.90(2) . ?
N1B C5B 1.333(2) . ?
N1B C4B 1.340(2) . ?
N1B H1B 0.99(2) . ?
C4B C3B 1.379(2) . ?
C4B H4B 0.96(2) . ?
C2B C3B 1.381(2) . ?
C2B C6B 1.397(2) . ?
C2B C1B 1.509(2) . ?
C6B C5B 1.370(2) . ?
C6B H6B 0.92(2) . ?
C3B H3B 0.92(2) . ?
C5B H5B 0.965(19) . ?
O6A N2A 1.2222(17) . ?
O5A N2A 1.2277(17) . ?
O2A C1A 1.239(2) . ?
O4A N1A 1.2214(17) . ?
O1A C1A 1.261(2) . ?
O3A N1A 1.2289(18) . ?
N1A C4A 1.470(2) . ?
N2A C6A 1.471(2) . ?
C4A C5A 1.382(2) . ?
C4A C3A 1.384(2) . ?
C3A C2A 1.390(2) . ?
C3A H3A 0.960(19) . ?
C5A C6A 1.382(2) . ?
C5A H5A 0.98(2) . ?
C6A C7A 1.382(2) . ?
C2A C7A 1.391(2) . ?
C2A C1A 1.516(2) . ?
C7A H7A 0.929(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
C1B N2B H2BA 118.0(12) . . ?
C1B N2B H2BB 122.2(13) . . ?
H2BA N2B H2BB 119.7(18) . . ?
C5B N1B C4B 121.34(15) . . ?
C5B N1B H1B 116.3(14) . . ?
C4B N1B H1B 122.4(14) . . ?
N1B C4B C3B 120.25(17) . . ?
N1B C4B H4B 117.6(10) . . ?
C3B C4B H4B 122.1(10) . . ?
C3B C2B C6B 119.10(15) . . ?
C3B C2B C1B 118.60(15) . . ?
C6B C2B C1B 122.30(16) . . ?
C5B C6B C2B 118.79(17) . . ?
C5B C6B H6B 119.4(11) . . ?
C2B C6B H6B 121.8(11) . . ?
C4B C3B C2B 119.41(16) . . ?
C4B C3B H3B 119.6(14) . . ?
C2B C3B H3B 120.8(14) . . ?
O1B C1B N2B 123.40(16) . . ?
O1B C1B C2B 118.88(15) . . ?
N2B C1B C2B 117.71(14) . . ?
N1B C5B C6B 121.09(16) . . ?
N1B C5B H5B 115.6(12) . . ?
C6B C5B H5B 123.3(12) . . ?
O4A N1A O3A 124.65(14) . . ?
O4A N1A C4A 117.68(14) . . ?
O3A N1A C4A 117.67(13) . . ?
O6A N2A O5A 124.20(14) . . ?
O6A N2A C6A 117.41(13) . . ?
O5A N2A C6A 118.39(13) . . ?
C5A C4A C3A 123.05(16) . . ?
C5A C4A N1A 117.77(14) . . ?
C3A C4A N1A 119.18(15) . . ?
C4A C3A C2A 119.26(16) . . ?
C4A C3A H3A 118.1(11) . . ?
C2A C3A H3A 122.6(10) . . ?
C6A C5A C4A 115.97(15) . . ?
C6A C5A H5A 123.3(12) . . ?
C4A C5A H5A 120.7(12) . . ?
C5A C6A C7A 123.26(16) . . ?
C5A C6A N2A 117.72(14) . . ?
C7A C6A N2A 119.00(15) . . ?
C3A C2A C7A 119.28(15) . . ?
C3A C2A C1A 120.13(15) . . ?
C7A C2A C1A 120.58(15) . . ?
O2A C1A O1A 127.08(15) . . ?
O2A C1A C2A 118.37(15) . . ?
O1A C1A C2A 114.54(15) . . ?
C6A C7A C2A 119.10(16) . . ?
C6A C7A H7A 120.0(11) . . ?
C2A C7A H7A 120.9(11) . . ?

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
N2B H2BA O1B 0.92(2) 2.01(2) 2.9272(19) 177.2(18) 2_545
N2B H2BB O2A 0.90(2) 1.99(2) 2.8759(19) 166.3(19) 1_545
N1B H1B O1A 0.99(2) 1.57(2) 2.5370(18) 163(2) .
C4B H4B O5A 0.96(2) 2.54(2) 3.455(2) 158.5(15) 1_554
C6B H6B O2A 0.92(2) 2.349(19) 3.172(2) 148.7(16) 1_545
C3B H3B O4A 0.92(2) 2.56(2) 3.313(2) 138.9(17) 1_544
C5B H5B O3A 0.965(19) 2.474(19) 3.422(2) 167.5(15) 1_545
C5A H5A O5A 0.98(2) 2.48(2) 3.449(2) 168.6(16) 2_667

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-4


_database_code_depnum_ccdc_archive 'CCDC 980364'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_35dnba_ina_3aba

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 3,5-dinitrobenzoic acid isonicotinamide 3-aminobenzoic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H4 N2 O6; C6 H7 N2 O; C7 H6 N O2'
_chemical_formula_sum            'C20 H17 N5 O9'
_chemical_formula_weight         471.39

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0678(4)
_cell_length_b                   8.8189(5)
_cell_length_c                   16.2172(9)
_cell_angle_alpha                93.761(5)
_cell_angle_beta                 90.458(5)
_cell_angle_gamma                95.498(5)
_cell_volume                     1003.90(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2186
_cell_measurement_theta_min      2.8884
_cell_measurement_theta_max      28.1815

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77944
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;
'Enhance (Mo) X-ray Source'   
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -5.00   21.00   1.0000   38.2900
omega____ theta____ kappa____ phi______ frames
    -      -21.0746   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00  106.00   1.0000   38.2900
omega____ theta____ kappa____ phi______ frames
    -       22.4808   77.0000  -60.0000 123

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00  104.00   1.0000   38.2900
omega____ theta____ kappa____ phi______ frames
    -       22.4808   77.0000   60.0000 120

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00  102.00   1.0000   38.2900
omega____ theta____ kappa____ phi______ frames
    -       22.4808   77.0000 -180.0000 112

;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7010
_diffrn_reflns_av_unetI/netI     0.1030
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.141
_diffrn_reflns_theta_max         28.253
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.893
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4447
_reflns_number_gt                2430
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_structure_solution    SHELXL97
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0226P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4447
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.0634
_refine_ls_wR_factor_gt          0.0585
_refine_ls_goodness_of_fit_ref   0.781
_refine_ls_restrained_S_all      0.781
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.05118(17) 0.61160(13) -0.18739(7) 0.0211(3) Uani 1 1 d . . . . .
H1A H 0.107(3) 0.679(3) -0.1317(12) 0.067(7) Uiso 1 1 d . . . . .
O2A O 0.13474(16) 0.40654(13) -0.12665(7) 0.0221(3) Uani 1 1 d . . . . .
O3A O -0.20538(18) 0.55918(14) -0.46672(7) 0.0312(3) Uani 1 1 d . . . . .
O4A O -0.25472(18) 0.33723(14) -0.53190(7) 0.0271(3) Uani 1 1 d . . . . .
O5A O -0.06941(18) -0.10642(14) -0.40692(7) 0.0297(3) Uani 1 1 d . . . . .
O6A O -0.02721(18) -0.09415(14) -0.27363(8) 0.0331(4) Uani 1 1 d . . . . .
N1A N -0.1985(2) 0.42058(18) -0.47148(8) 0.0198(4) Uani 1 1 d . . . . .
N2A N -0.0479(2) -0.03564(17) -0.33935(9) 0.0210(4) Uani 1 1 d . . . . .
C1A C 0.0700(2) 0.4657(2) -0.18507(10) 0.0148(4) Uani 1 1 d . . . . .
C2A C 0.0039(2) 0.37447(19) -0.26267(10) 0.0129(4) Uani 1 1 d . . . . .
C3A C 0.0077(2) 0.2177(2) -0.26532(10) 0.0150(4) Uani 1 1 d . . . . .
H3A H 0.0491 0.1699 -0.2185 0.018 Uiso 1 1 calc R U . . .
C4A C -0.0493(2) 0.13171(19) -0.33688(10) 0.0147(4) Uani 1 1 d . . . . .
C5A C -0.1112(2) 0.19594(19) -0.40582(10) 0.0157(4) Uani 1 1 d . . . . .
H5A H -0.1470 0.1355 -0.4551 0.019 Uiso 1 1 calc R U . . .
C6A C -0.1190(2) 0.3508(2) -0.40050(10) 0.0149(4) Uani 1 1 d . . . . .
C7A C -0.0604(2) 0.44323(19) -0.33072(10) 0.0148(4) Uani 1 1 d . . . . .
H7A H -0.0643 0.5507 -0.3295 0.018 Uiso 1 1 calc R U . . .
O1B O 0.37701(16) 1.23546(13) 0.14091(7) 0.0195(3) Uani 1 1 d . . . . .
N1B N 0.18257(19) 0.81510(16) -0.07181(8) 0.0165(3) Uani 1 1 d . . . . .
N2B N 0.3160(2) 1.36968(18) 0.03174(10) 0.0196(4) Uani 1 1 d . . . . .
H2BA H 0.345(3) 1.464(2) 0.0652(11) 0.045(6) Uiso 1 1 d . . . . .
H2BB H 0.272(3) 1.372(2) -0.0178(12) 0.044(7) Uiso 1 1 d . . . . .
C1B C 0.3273(2) 1.2399(2) 0.06717(10) 0.0154(4) Uani 1 1 d . . . . .
C2B C 0.2785(2) 1.09319(19) 0.01676(10) 0.0127(4) Uani 1 1 d . . . . .
C3B C 0.2952(2) 1.08027(19) -0.06841(10) 0.0154(4) Uani 1 1 d . . . . .
H3B H 0.3398 1.1662 -0.0977 0.018 Uiso 1 1 calc R U . . .
C4B C 0.2456(2) 0.93993(19) -0.11003(10) 0.0164(4) Uani 1 1 d . . . . .
H4B H 0.2567 0.9317 -0.1685 0.020 Uiso 1 1 calc R U . . .
C5B C 0.1701(2) 0.82788(19) 0.01063(10) 0.0165(4) Uani 1 1 d . . . . .
H5B H 0.1271 0.7399 0.0385 0.020 Uiso 1 1 calc R U . . .
C6B C 0.2171(2) 0.96333(19) 0.05676(10) 0.0158(4) Uani 1 1 d . . . . .
H6B H 0.2076 0.9678 0.1153 0.019 Uiso 1 1 calc R U . . .
O1C O 0.47831(18) 0.46711(14) 0.24397(7) 0.0236(3) Uani 1 1 d . . . . .
H1C H 0.432(3) 0.390(2) 0.1992(12) 0.064(7) Uiso 1 1 d . . . . .
O2C O 0.39768(16) 0.62886(13) 0.15151(7) 0.0194(3) Uani 1 1 d . . . . .
N1C N 0.5143(2) 1.14522(19) 0.30791(11) 0.0293(4) Uani 1 1 d . . . . .
H1CA H 0.462(3) 1.171(2) 0.2599(13) 0.056(7) Uiso 1 1 d . . . . .
H1CB H 0.549(3) 1.226(2) 0.3466(12) 0.057(7) Uiso 1 1 d . . . . .
C1C C 0.4576(2) 0.6053(2) 0.22018(11) 0.0162(4) Uani 1 1 d . . . . .
C2C C 0.5116(2) 0.72823(19) 0.28529(10) 0.0127(4) Uani 1 1 d . . . . .
C3C C 0.4907(2) 0.87783(19) 0.26722(10) 0.0154(4) Uani 1 1 d . . . . .
H3C H 0.4452 0.8980 0.2141 0.018 Uiso 1 1 calc R U . . .
C4C C 0.5357(2) 0.99824(19) 0.32596(10) 0.0155(4) Uani 1 1 d . . . . .
C5C C 0.6018(2) 0.9652(2) 0.40337(10) 0.0178(4) Uani 1 1 d . . . . .
H5C H 0.6326 1.0459 0.4444 0.021 Uiso 1 1 calc R U . . .
C6C C 0.6230(2) 0.81675(19) 0.42123(10) 0.0169(4) Uani 1 1 d . . . . .
H6C H 0.6688 0.7967 0.4743 0.020 Uiso 1 1 calc R U . . .
C7C C 0.5781(2) 0.6966(2) 0.36269(9) 0.0155(4) Uani 1 1 d . . . . .
H7C H 0.5924 0.5945 0.3752 0.019 Uiso 1 1 calc R U . . .


_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
O1A C1A 1.3093(19) . ?
O1A H1A 1.10(2) . ?
O2A C1A 1.2175(18) . ?
O3A N1A 1.2253(18) . ?
O4A N1A 1.2255(17) . ?
O5A N2A 1.2259(16) . ?
O6A N2A 1.2279(16) . ?
N1A C6A 1.473(2) . ?
N2A C4A 1.475(2) . ?
C1A C2A 1.495(2) . ?
C2A C3A 1.384(2) . ?
C2A C7A 1.387(2) . ?
C3A C4A 1.379(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.373(2) . ?
C5A C6A 1.369(2) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.387(2) . ?
C7A H7A 0.9500 . ?
O1B C1B 1.2477(18) . ?
N1B C5B 1.3385(19) . ?
N1B C4B 1.3395(19) . ?
N2B C1B 1.323(2) . ?
N2B H2BA 0.967(19) . ?
N2B H2BB 0.864(18) . ?
C1B C2B 1.494(2) . ?
C2B C3B 1.385(2) . ?
C2B C6B 1.388(2) . ?
C3B C4B 1.383(2) . ?
C3B H3B 0.9500 . ?
C4B H4B 0.9500 . ?
C5B C6B 1.378(2) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
O1C C1C 1.323(2) . ?
O1C H1C 0.99(2) . ?
O2C C1C 1.2257(18) . ?
N1C C4C 1.369(2) . ?
N1C H1CA 0.91(2) . ?
N1C H1CB 0.93(2) . ?
C1C C2C 1.483(2) . ?
C2C C7C 1.391(2) . ?
C2C C3C 1.391(2) . ?
C3C C4C 1.391(2) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.394(2) . ?
C5C C6C 1.381(2) . ?
C5C H5C 0.9500 . ?
C6C C7C 1.387(2) . ?
C6C H6C 0.9500 . ?
C7C H7C 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
C1A O1A H1A 112.9(11) . . ?
O3A N1A O4A 123.53(15) . . ?
O3A N1A C6A 118.06(14) . . ?
O4A N1A C6A 118.41(15) . . ?
O5A N2A O6A 124.73(15) . . ?
O5A N2A C4A 117.51(14) . . ?
O6A N2A C4A 117.75(14) . . ?
O2A C1A O1A 124.85(15) . . ?
O2A C1A C2A 121.82(16) . . ?
O1A C1A C2A 113.33(14) . . ?
C3A C2A C7A 120.13(15) . . ?
C3A C2A C1A 118.20(15) . . ?
C7A C2A C1A 121.67(15) . . ?
C4A C3A C2A 119.11(15) . . ?
C4A C3A H3A 120.4 . . ?
C2A C3A H3A 120.4 . . ?
C5A C4A C3A 122.39(16) . . ?
C5A C4A N2A 118.45(15) . . ?
C3A C4A N2A 119.15(14) . . ?
C6A C5A C4A 117.17(15) . . ?
C6A C5A H5A 121.4 . . ?
C4A C5A H5A 121.4 . . ?
C5A C6A C7A 122.95(15) . . ?
C5A C6A N1A 118.07(15) . . ?
C7A C6A N1A 118.96(15) . . ?
C6A C7A C2A 118.20(16) . . ?
C6A C7A H7A 120.9 . . ?
C2A C7A H7A 120.9 . . ?
C5B N1B C4B 117.81(15) . . ?
C1B N2B H2BA 118.0(11) . . ?
C1B N2B H2BB 122.1(13) . . ?
H2BA N2B H2BB 119.5(17) . . ?
O1B C1B N2B 122.54(17) . . ?
O1B C1B C2B 118.90(15) . . ?
N2B C1B C2B 118.56(15) . . ?
C3B C2B C6B 118.33(16) . . ?
C3B C2B C1B 122.77(15) . . ?
C6B C2B C1B 118.89(15) . . ?
C4B C3B C2B 118.75(16) . . ?
C4B C3B H3B 120.6 . . ?
C2B C3B H3B 120.6 . . ?
N1B C4B C3B 123.08(16) . . ?
N1B C4B H4B 118.5 . . ?
C3B C4B H4B 118.5 . . ?
N1B C5B C6B 122.78(16) . . ?
N1B C5B H5B 118.6 . . ?
C6B C5B H5B 118.6 . . ?
C5B C6B C2B 119.23(16) . . ?
C5B C6B H6B 120.4 . . ?
C2B C6B H6B 120.4 . . ?
C1C O1C H1C 109.2(12) . . ?
C4C N1C H1CA 123.8(13) . . ?
C4C N1C H1CB 120.4(12) . . ?
H1CA N1C H1CB 115.8(17) . . ?
O2C C1C O1C 123.22(16) . . ?
O2C C1C C2C 123.54(16) . . ?
O1C C1C C2C 113.23(15) . . ?
C7C C2C C3C 120.43(15) . . ?
C7C C2C C1C 121.75(15) . . ?
C3C C2C C1C 117.81(14) . . ?
C4C C3C C2C 120.75(15) . . ?
C4C C3C H3C 119.6 . . ?
C2C C3C H3C 119.6 . . ?
N1C C4C C3C 120.50(16) . . ?
N1C C4C C5C 121.16(16) . . ?
C3C C4C C5C 118.34(16) . . ?
C6C C5C C4C 120.91(16) . . ?
C6C C5C H5C 119.5 . . ?
C4C C5C H5C 119.5 . . ?
C5C C6C C7C 120.80(16) . . ?
C5C C6C H6C 119.6 . . ?
C7C C6C H6C 119.6 . . ?
C6C C7C C2C 118.77(16) . . ?
C6C C7C H7C 120.6 . . ?
C2C C7C H7C 120.6 . . ?

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
C3B H3B O2C 0.95 2.66 3.542(2) 155.0 2_675
C5B H5B O2A 0.95 2.64 3.490(2) 149.4 2_565
C4B H4B O6A 0.95 2.61 3.248(2) 125.2 1_565
C5C H5C O4A 0.95 2.62 3.434(2) 144.1 1_666
N2B H2BA O2C 0.967(19) 1.96(2) 2.9115(19) 168.6(15) 1_565
O1C H1C O1B 0.99(2) 1.62(2) 2.5946(16) 165.8(19) 1_545
N1C H1CA O1C 0.91(2) 2.63(2) 3.118(2) 113.9(15) 1_565
N1C H1CA O1B 0.91(2) 2.14(2) 3.049(2) 172.2(17) .
N1C H1CB O4A 0.93(2) 2.49(2) 3.333(2) 150.2(17) 1_666
N2B H2BB O2A 0.864(18) 2.059(19) 2.9123(19) 169.6(18) 1_565
O1A H1A N1B 1.10(2) 1.55(2) 2.6093(17) 161.6(18) .

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-4


_database_code_depnum_ccdc_archive 'CCDC 980365'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_246thba_ina

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 pyridinium-4-carboxamide 2,4,6-trihydroxybenzoate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 O5, C6 H7 N2 O'
_chemical_formula_sum            'C13 H12 N2 O6'
_chemical_formula_weight         292.25

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.8093(14)
_cell_length_b                   13.1563(12)
_cell_length_c                   7.4708(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1259.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
;
'Enhance (Mo) X-ray Source'  
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3389
_diffrn_reflns_av_unetI/netI     0.0816
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_theta_min         3.136
_diffrn_reflns_theta_max         28.419
_diffrn_reflns_theta_full        26.500
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.573
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1815
_reflns_number_gt                1244
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.189
_reflns_Friedel_fraction_max     0.197
_reflns_Friedel_fraction_full    0.236

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
 CrysAlis CCD, Oxford Diffraction Ltd.,
 Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
 (compiled Jan 8 2009,16:24:04)
;

_computing_cell_refinement       
;
 CrysAlis CCD, Oxford Diffraction Ltd.,
 Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
 (compiled Jan 8 2009,16:24:04)
;

_computing_data_reduction        
;
 CrysAlis CCD, Oxford Diffraction Ltd.,
 Version 1.171.33.31 (release 08-01-2009 CrysAlis171 .NET)
 (compiled Jan 8 2009,16:24:04)
;
_computing_structure_solution    'Sir92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0136P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 187 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.4(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1815
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0482
_refine_ls_wR_factor_gt          0.0453
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_restrained_S_all      0.825
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O16 O 0.57332(16) 0.68902(14) 1.2147(3) 0.0242(6) Uani 1 1 d . . . . .
N4 N 0.9204(2) 0.70103(17) 0.9242(3) 0.0157(6) Uani 1 1 d . . . . .
H4 H 0.984(3) 0.719(2) 0.849(5) 0.057(11) Uiso 1 1 d . . . . .
C9 C 0.7374(2) 0.64604(19) 1.0865(4) 0.0133(7) Uani 1 1 d . . . . .
C5 C 0.8021(2) 0.5738(2) 1.0107(4) 0.0173(7) Uani 1 1 d . . . . .
H5 H 0.785(2) 0.5025(18) 1.012(3) 0.017(8) Uiso 1 1 d . . . . .
N14 N 0.6124(2) 0.52256(19) 1.1943(4) 0.0225(7) Uani 1 1 d . . . . .
C3 C 0.8934(3) 0.6027(2) 0.9306(4) 0.0187(7) Uani 1 1 d . . . . .
H3 H 0.9399(18) 0.5558(17) 0.871(3) 0.013(8) Uiso 1 1 d . . . . .
C6 C 0.8596(3) 0.7730(2) 0.9965(4) 0.0187(8) Uani 1 1 d . . . . .
H6 H 0.884(2) 0.842(2) 0.984(4) 0.032(9) Uiso 1 1 d . . . . .
C13 C 0.6336(2) 0.6209(2) 1.1720(4) 0.0177(7) Uani 1 1 d . . . . .
C10 C 0.7671(2) 0.7474(2) 1.0786(4) 0.0182(7) Uani 1 1 d . . . . .
H10 H 0.7255(18) 0.8005(17) 1.131(4) 0.012(8) Uiso 1 1 d . . . . .
H14A H 0.663(3) 0.473(3) 1.146(6) 0.075(14) Uiso 1 1 d . . . . .
H14B H 0.549(2) 0.4997(19) 1.240(4) 0.037(10) Uiso 1 1 d . . . . .
O31 O 0.90500(16) 0.27063(13) 1.2477(3) 0.0211(5) Uani 1 1 d . . . . .
C26 C 0.7767(2) 0.16748(19) 1.1128(4) 0.0146(7) Uani 1 1 d . . . . .
C20 C 0.6450(3) 0.0577(2) 0.9810(4) 0.0197(8) Uani 1 1 d . . . . .
H20 H 0.623(2) -0.0071(18) 0.953(3) 0.008(7) Uiso 1 1 d . . . . .
O25 O 0.79244(15) -0.01405(14) 1.1187(3) 0.0245(6) Uani 1 1 d . . . . .
O17 O 0.49500(17) 0.12703(14) 0.8446(3) 0.0244(5) Uani 1 1 d . . . . .
H17 H 0.462(3) 0.195(3) 0.794(7) 0.127(18) Uiso 1 1 d . . . . .
C18 C 0.5868(2) 0.1427(2) 0.9346(4) 0.0189(7) Uani 1 1 d . . . . .
C24 C 0.7143(2) 0.25014(19) 1.0655(4) 0.0167(7) Uani 1 1 d . . . . .
C22 C 0.7379(2) 0.0702(2) 1.0701(4) 0.0183(7) Uani 1 1 d . . . . .
C21 C 0.6202(3) 0.2399(2) 0.9778(4) 0.0154(7) Uani 1 1 d . . . . .
H21 H 0.577(2) 0.2998(19) 0.943(4) 0.025(9) Uiso 1 1 d . . . . .
C29 C 0.8756(2) 0.1797(2) 1.2104(4) 0.0186(7) Uani 1 1 d . . . . .
O0AA O 0.92817(14) 0.10316(13) 1.2575(3) 0.0221(5) Uani 1 1 d . . . . .
O28 O 0.74659(18) 0.34661(14) 1.1080(3) 0.0224(6) Uani 1 1 d . . . . .
H28 H 0.807(2) 0.341(2) 1.155(5) 0.047(12) Uiso 1 1 d . . . . .
H25 H 0.856(2) 0.018(2) 1.186(4) 0.040(10) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O16 C13 1.225(3) . ?
N4 C6 1.340(4) . ?
N4 C3 1.340(3) . ?
N4 H4 1.02(4) . ?
C9 C5 1.382(4) . ?
C9 C10 1.388(4) . ?
C9 C13 1.511(4) . ?
C5 C3 1.367(4) . ?
C5 H5 0.96(2) . ?
N14 C13 1.333(3) . ?
N14 H14A 0.99(4) . ?
N14 H14B 0.93(3) . ?
C3 H3 0.97(2) . ?
C6 C10 1.376(4) . ?
C6 H6 0.97(3) . ?
C10 H10 0.96(2) . ?
O31 C29 1.285(3) . ?
C26 C24 1.395(3) . ?
C26 C22 1.409(4) . ?
C26 C29 1.470(4) . ?
C20 C22 1.375(4) . ?
C20 C18 1.387(4) . ?
C20 H20 0.92(2) . ?
O25 C22 1.360(3) . ?
O25 H25 1.04(3) . ?
O17 C18 1.370(4) . ?
O17 H17 1.06(4) . ?
C18 C21 1.387(4) . ?
C24 O28 1.372(3) . ?
C24 C21 1.379(4) . ?
C21 H21 1.00(3) . ?
C29 O0AA 1.262(3) . ?
O28 H28 0.85(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N4 C3 121.2(3) . . ?
C6 N4 H4 121.3(16) . . ?
C3 N4 H4 117.1(17) . . ?
C5 C9 C10 118.6(3) . . ?
C5 C9 C13 123.4(2) . . ?
C10 C9 C13 117.9(3) . . ?
C3 C5 C9 120.1(3) . . ?
C3 C5 H5 117.8(16) . . ?
C9 C5 H5 122.1(16) . . ?
C13 N14 H14A 118(2) . . ?
C13 N14 H14B 122.6(17) . . ?
H14A N14 H14B 119(3) . . ?
N4 C3 C5 120.3(3) . . ?
N4 C3 H3 116.2(14) . . ?
C5 C3 H3 123.5(14) . . ?
N4 C6 C10 120.5(3) . . ?
N4 C6 H6 116.3(19) . . ?
C10 C6 H6 123.2(19) . . ?
O16 C13 N14 123.3(3) . . ?
O16 C13 C9 120.3(3) . . ?
N14 C13 C9 116.4(3) . . ?
C6 C10 C9 119.3(3) . . ?
C6 C10 H10 118.8(14) . . ?
C9 C10 H10 121.9(14) . . ?
C24 C26 C22 116.7(2) . . ?
C24 C26 C29 122.3(2) . . ?
C22 C26 C29 121.0(3) . . ?
C22 C20 C18 119.3(3) . . ?
C22 C20 H20 118.7(16) . . ?
C18 C20 H20 122.0(16) . . ?
C22 O25 H25 101.2(15) . . ?
C18 O17 H17 113(2) . . ?
O17 C18 C21 121.2(3) . . ?
O17 C18 C20 117.5(3) . . ?
C21 C18 C20 121.3(3) . . ?
O28 C24 C21 117.6(3) . . ?
O28 C24 C26 119.3(3) . . ?
C21 C24 C26 123.0(3) . . ?
O25 C22 C20 118.4(3) . . ?
O25 C22 C26 120.0(3) . . ?
C20 C22 C26 121.6(3) . . ?
C24 C21 C18 118.1(3) . . ?
C24 C21 H21 122.0(16) . . ?
C18 C21 H21 119.9(16) . . ?
O0AA C29 O31 121.7(3) . . ?
O0AA C29 C26 120.7(3) . . ?
O31 C29 C26 117.5(3) . . ?
C24 O28 H28 106(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
O28 H28 O31 0.85(3) 1.70(3) 2.491(3) 152(3) .
O25 H25 O0AA 1.04(3) 1.55(3) 2.545(3) 158(3) .

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4



#END

_database_code_depnum_ccdc_archive 'CCDC 980366'
