# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_Zwitterion1
_database_code_depnum_ccdc_archive 'CCDC 1584660'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
(Z)-3-carbamoyl-1-(3-carboxy-1,1-dihydroxyprop-2-en-1-ide-2-yl)
pyridin-1-ium
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2 O5'
_chemical_formula_sum            'C10 H8 N2 O5'
_chemical_formula_weight         236.18

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8986(17)
_cell_length_b                   7.9933(15)
_cell_length_c                   14.175(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.628(3)
_cell_angle_gamma                90
_cell_volume                     999.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2701
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      28.24

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.419
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.083
_exptl_absorpt_coefficient_mu    0.129
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8572
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'INCOATEC I\ms HB'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX SMART CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            6143
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.309
_diffrn_reflns_theta_max         28.571
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2350
_reflns_number_gt                1879
_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       'APEX3 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0477P)²+0.4836P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2350
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_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
O1 O 0.80378(13) 0.52860(14) 0.32745(9) 0.0214(3) Uani 1 1 d . . . . .
O2 O 1.04130(13) 0.62061(15) 0.36967(9) 0.0232(3) Uani 1 1 d . . . . .
C3 C 0.93815(18) 0.5044(2) 0.35320(11) 0.0155(3) Uani 1 1 d . . . . .
C4 C 1.00542(18) 0.3337(2) 0.36974(11) 0.0162(3) Uani 1 1 d . . . . .
H4 H 1.112905 0.326285 0.377608 0.019 Uiso 1 1 calc R U . . .
C5 C 0.93008(18) 0.1922(2) 0.37449(11) 0.0161(3) Uani 1 1 d . . . . .
C6 C 1.00798(18) 0.0219(2) 0.38479(11) 0.0164(3) Uani 1 1 d . . . . .
O7 O 1.14048(13) 0.01531(15) 0.42285(9) 0.0211(3) Uani 1 1 d . . . . .
O8 O 0.92527(13) -0.09784(14) 0.35033(9) 0.0225(3) Uani 1 1 d . . . . .
N9 N 0.76511(15) 0.18728(17) 0.36814(10) 0.0167(3) Uani 1 1 d . . . . .
C10 C 0.68223(19) 0.1205(2) 0.29042(12) 0.0197(4) Uani 1 1 d . . . . .
H10 H 0.730079 0.088190 0.237199 0.024 Uiso 1 1 calc R U . . .
C11 C 0.52884(19) 0.0996(2) 0.28854(12) 0.0218(4) Uani 1 1 d . . . . .
H11 H 0.470311 0.051436 0.234402 0.026 Uiso 1 1 calc R U . . .
C12 C 0.45959(19) 0.1492(2) 0.36612(12) 0.0209(4) Uani 1 1 d . . . . .
H12 H 0.353994 0.131734 0.366130 0.025 Uiso 1 1 calc R U . . .
C13 C 0.54520(18) 0.2244(2) 0.44382(11) 0.0165(3) Uani 1 1 d . . . . .
C14 C 0.69942(18) 0.2413(2) 0.44368(11) 0.0168(3) Uani 1 1 d . . . . .
H14 H 0.759842 0.290890 0.496632 0.020 Uiso 1 1 calc R U . . .
C15 C 0.48327(18) 0.2929(2) 0.53006(12) 0.0185(4) Uani 1 1 d . . . . .
O16 O 0.56234(13) 0.38814(16) 0.58349(8) 0.0239(3) Uani 1 1 d . . . . .
N17 N 0.34387(15) 0.24328(19) 0.54359(10) 0.0220(3) Uani 1 1 d . . . . .
H17A H 0.303694 0.279255 0.593321 0.026 Uiso 1 1 calc R U . . .
H17B H 0.292519 0.174699 0.502738 0.026 Uiso 1 1 calc R U . . .
H2 H 0.991(3) 0.738(4) 0.362(2) 0.077(9) 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
O1 C3 1.2184(19) . ?
O2 C3 1.3051(19) . ?
O2 H2 1.04(3) . ?
C3 C4 1.496(2) . ?
C4 C5 1.321(2) . ?
C4 H4 0.9500 . ?
C5 N9 1.459(2) . ?
C5 C6 1.526(2) . ?
C6 O7 1.231(2) . ?
C6 O8 1.2651(19) . ?
N9 C10 1.351(2) . ?
N9 C14 1.357(2) . ?
C10 C11 1.372(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(2) . ?
C13 C15 1.509(2) . ?
C14 H14 0.9500 . ?
C15 O16 1.227(2) . ?
C15 N17 1.340(2) . ?
N17 H17A 0.8800 . ?
N17 H17B 0.8800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 H2 110.0(15) . . ?
O1 C3 O2 125.42(15) . . ?
O1 C3 C4 123.24(14) . . ?
O2 C3 C4 111.34(13) . . ?
C5 C4 C3 126.42(15) . . ?
C5 C4 H4 116.8 . . ?
C3 C4 H4 116.8 . . ?
C4 C5 N9 122.23(15) . . ?
C4 C5 C6 122.79(14) . . ?
N9 C5 C6 114.97(13) . . ?
O7 C6 O8 127.68(15) . . ?
O7 C6 C5 118.46(14) . . ?
O8 C6 C5 113.85(13) . . ?
C10 N9 C14 121.56(14) . . ?
C10 N9 C5 119.77(14) . . ?
C14 N9 C5 118.55(13) . . ?
N9 C10 C11 119.85(16) . . ?
N9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 119.68(15) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 119.81(16) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 118.81(15) . . ?
C14 C13 C15 115.86(14) . . ?
C12 C13 C15 125.33(15) . . ?
N9 C14 C13 120.20(15) . . ?
N9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
O16 C15 N17 124.13(16) . . ?
O16 C15 C13 118.93(15) . . ?
N17 C15 C13 116.93(14) . . ?
C15 N17 H17A 120.0 . . ?
C15 N17 H17B 120.0 . . ?
H17A N17 H17B 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 C5 -11.8(3) . . . . ?
O2 C3 C4 C5 168.29(16) . . . . ?
C3 C4 C5 N9 -3.0(3) . . . . ?
C3 C4 C5 C6 175.64(14) . . . . ?
C4 C5 C6 O7 26.3(2) . . . . ?
N9 C5 C6 O7 -154.94(15) . . . . ?
C4 C5 C6 O8 -152.52(16) . . . . ?
N9 C5 C6 O8 26.2(2) . . . . ?
C4 C5 N9 C10 110.52(19) . . . . ?
C6 C5 N9 C10 -68.21(19) . . . . ?
C4 C5 N9 C14 -73.4(2) . . . . ?
C6 C5 N9 C14 107.88(16) . . . . ?
C14 N9 C10 C11 -2.8(2) . . . . ?
C5 N9 C10 C11 173.14(15) . . . . ?
N9 C10 C11 C12 0.8(3) . . . . ?
C10 C11 C12 C13 2.0(3) . . . . ?
C11 C12 C13 C14 -2.9(3) . . . . ?
C11 C12 C13 C15 176.36(16) . . . . ?
C10 N9 C14 C13 1.9(2) . . . . ?
C5 N9 C14 C13 -174.09(14) . . . . ?
C12 C13 C14 N9 1.0(2) . . . . ?
C15 C13 C14 N9 -178.37(14) . . . . ?
C14 C13 C15 O16 15.3(2) . . . . ?
C12 C13 C15 O16 -164.02(16) . . . . ?
C14 C13 C15 N17 -164.11(15) . . . . ?
C12 C13 C15 N17 16.6(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
O2 H2 O7 1.04(3) 2.67(3) 3.3353(18) 121.8(19) 1_565
O2 H2 O8 1.04(3) 1.44(3) 2.4760(17) 179(3) 1_565

_refine_diff_density_max         0.484
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_Salt2a
_database_code_depnum_ccdc_archive 'CCDC 1584662'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H7 N2 O, 0.5(C4 O4)'
_chemical_formula_sum            'C8 H7 N2 O3'
_chemical_formula_weight         179.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   3.671(3)
_cell_length_b                   7.594(5)
_cell_length_c                   13.772(10)
_cell_angle_alpha                95.723(8)
_cell_angle_beta                 93.218(8)
_cell_angle_gamma                97.153(8)
_cell_volume                     378.1(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1886
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      28.38

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             186
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8473
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'INCOATEC I\ms HB'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX SMART CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            4363
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.490
_diffrn_reflns_theta_max         28.592
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1758
_reflns_number_gt                1466
_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       'APEX3 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0649P)²+0.0470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1758
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1158
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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
N1 N 0.5150(3) 0.51222(15) 0.19648(8) 0.0142(3) Uani 1 1 d . . . . .
C2 C 0.5395(4) 0.56960(18) 0.29219(10) 0.0148(3) Uani 1 1 d . . . . .
H2 H 0.481475 0.685179 0.313237 0.018 Uiso 1 1 calc R U . . .
C3 C 0.6488(4) 0.46151(17) 0.36039(10) 0.0142(3) Uani 1 1 d . . . . .
H3 H 0.669042 0.502670 0.428157 0.017 Uiso 1 1 calc R U . . .
C4 C 0.7289(3) 0.29141(17) 0.32860(9) 0.0125(3) Uani 1 1 d . . . . .
C5 C 0.7037(4) 0.23616(17) 0.22902(10) 0.0136(3) Uani 1 1 d . . . . .
H5 H 0.759977 0.121306 0.205782 0.016 Uiso 1 1 calc R U . . .
C6 C 0.5953(4) 0.35066(17) 0.16397(10) 0.0149(3) Uani 1 1 d . . . . .
H6 H 0.577873 0.314094 0.095673 0.018 Uiso 1 1 calc R U . . .
C7 C 0.8368(3) 0.17370(17) 0.40536(10) 0.0134(3) Uani 1 1 d . . . . .
O8 O 0.8115(3) 0.22324(13) 0.49263(7) 0.0185(3) Uani 1 1 d . . . . .
N9 N 0.9564(3) 0.02136(15) 0.37304(8) 0.0162(3) Uani 1 1 d . . . . .
H9A H 1.023285 -0.050968 0.414852 0.019 Uiso 1 1 calc R U . . .
H9B H 0.968485 -0.006941 0.309866 0.019 Uiso 1 1 calc R U . . .
O10 O 0.1058(3) 0.86774(13) 0.18716(7) 0.0194(3) Uani 1 1 d . . . . .
O11 O 0.2944(3) 0.69612(12) 0.06379(7) 0.0179(3) Uani 1 1 d . . . . .
C12 C 0.1542(4) 0.83030(17) 0.09970(10) 0.0131(3) Uani 1 1 d . . . . .
C13 C 0.0440(4) 0.95012(17) 0.02844(10) 0.0149(3) Uani 1 1 d . . . . .
H1 H 0.415(6) 0.592(3) 0.1449(17) 0.056(6) 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
N1 C6 1.3371(19) . ?
N1 C2 1.341(2) . ?
N1 H1 1.06(2) . ?
C2 C3 1.3821(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 C7 1.5175(18) . ?
C5 C6 1.3850(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O8 1.2352(19) . ?
C7 N9 1.3322(18) . ?
N9 H9A 0.8800 . ?
N9 H9B 0.8800 . ?
O10 C12 1.2376(18) . ?
O11 C12 1.2673(17) . ?
C12 C13 1.4765(18) . ?
C13 C13 1.201(3) 2_575 ?

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 N1 C2 121.60(11) . . ?
C6 N1 H1 118.3(13) . . ?
C2 N1 H1 120.0(13) . . ?
N1 C2 C3 120.36(13) . . ?
N1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 119.24(13) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.10(11) . . ?
C5 C4 C7 122.87(12) . . ?
C3 C4 C7 118.03(13) . . ?
C6 C5 C4 119.14(13) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
N1 C6 C5 120.56(13) . . ?
N1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O8 C7 N9 124.06(11) . . ?
O8 C7 C4 119.21(12) . . ?
N9 C7 C4 116.73(13) . . ?
C7 N9 H9A 120.0 . . ?
C7 N9 H9B 120.0 . . ?
H9A N9 H9B 120.0 . . ?
O10 C12 O11 125.96(11) . . ?
O10 C12 C13 118.82(12) . . ?
O11 C12 C13 115.22(13) . . ?
C13 C13 C12 179.0(2) 2_575 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 -0.18(19) . . . . ?
N1 C2 C3 C4 -0.8(2) . . . . ?
C2 C3 C4 C5 1.22(19) . . . . ?
C2 C3 C4 C7 -178.16(11) . . . . ?
C3 C4 C5 C6 -0.77(19) . . . . ?
C7 C4 C5 C6 178.58(12) . . . . ?
C2 N1 C6 C5 0.65(19) . . . . ?
C4 C5 C6 N1 -0.2(2) . . . . ?
C5 C4 C7 O8 -171.48(12) . . . . ?
C3 C4 C7 O8 7.87(18) . . . . ?
C5 C4 C7 N9 8.84(19) . . . . ?
C3 C4 C7 N9 -171.80(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
N1 H1 O11 1.06(2) 1.51(2) 2.5631(18) 174(2) .
N9 H9A O8 0.88 2.04 2.9156(19) 177.7 2_756
N9 H9B O10 0.88 1.98 2.817(2) 159.1 1_645

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_3Melamine
_database_code_depnum_ccdc_archive 'CCDC 1584665'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
2,4,6-triamino-1,3,5-triazin-1-ium 
2-(4-cyanopyridin-1-ium-1-yl)fumarate hydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H5 N2 O4, C3 H7 N6, H2 O'
_chemical_formula_sum            'C13 H14 N8 O5'
_chemical_formula_weight         362.32

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.184(15)
_cell_length_b                   7.328(5)
_cell_length_c                   13.045(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.257(10)
_cell_angle_gamma                90
_cell_volume                     1531(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1392
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      21.11

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.033
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8905
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX DUO CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            16377
_diffrn_reflns_av_unetI/netI     0.0659
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.271
_diffrn_reflns_theta_max         27.212
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3395
_reflns_number_gt                1814
_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       'APEX3 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0560P)²+0.8182P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3395
_refine_ls_number_parameters     271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1228
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1593
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.054
_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
O1 O 0.63903(15) 0.5812(6) 0.5463(2) 0.1005(14) Uani 1 1 d . . . . .
O2 O 0.71625(14) 0.4415(4) 0.6956(2) 0.0548(7) Uani 1 1 d . . . . .
C3 C 0.70641(18) 0.5230(5) 0.6101(3) 0.0417(9) Uani 1 1 d . . . . .
C4 C 0.78439(19) 0.5627(5) 0.5864(3) 0.0410(8) Uani 1 1 d . . . . .
H4 H 0.835562 0.564904 0.647648 0.049 Uiso 1 1 calc R U . . .
C5 C 0.78846(18) 0.5943(5) 0.4901(2) 0.0357(8) Uani 1 1 d . . . . .
C6 C 0.86628(18) 0.6402(4) 0.4645(3) 0.0351(8) Uani 1 1 d . . . . .
O7 O 0.93172(12) 0.6837(3) 0.54173(17) 0.0445(6) Uani 1 1 d . . . . .
O8 O 0.85594(13) 0.6307(4) 0.36624(18) 0.0521(7) Uani 1 1 d . . . . .
N9 N 0.71140(13) 0.5858(3) 0.39176(19) 0.0287(6) Uani 1 1 d . . . . .
C10 C 0.67790(17) 0.7437(4) 0.3431(2) 0.0337(7) Uani 1 1 d . . . . .
H10 H 0.704458 0.856361 0.371236 0.040 Uiso 1 1 calc R U . . .
C11 C 0.60565(18) 0.7415(5) 0.2534(3) 0.0379(8) Uani 1 1 d . . . . .
H11 H 0.580952 0.852761 0.219697 0.046 Uiso 1 1 calc R U . . .
C12 C 0.56876(16) 0.5780(5) 0.2118(2) 0.0336(7) Uani 1 1 d . . . . .
C13 C 0.60612(18) 0.4158(5) 0.2601(3) 0.0396(8) Uani 1 1 d . . . . .
H13 H 0.582425 0.301587 0.230368 0.048 Uiso 1 1 calc R U . . .
C14 C 0.67773(17) 0.4238(4) 0.3513(2) 0.0354(7) Uani 1 1 d . . . . .
H14 H 0.703712 0.314340 0.386136 0.042 Uiso 1 1 calc R U . . .
C15 C 0.4888(2) 0.5721(5) 0.1220(3) 0.0448(9) Uani 1 1 d . . . . .
N16 N 0.42454(18) 0.5668(5) 0.0551(3) 0.0620(10) Uani 1 1 d . . . . .
N17 N 0.94444(14) 0.2935(4) 1.0391(2) 0.0311(6) Uani 1 1 d . . . . .
H17 H 0.9825(18) 0.250(4) 1.015(2) 0.037(9) Uiso 1 1 d . . . . .
H26B H 0.442(3) 0.571(7) 0.421(4) 0.114(18) Uiso 1 1 d . . . . .
H26A H 0.545(3) 0.605(9) 0.447(4) 0.18(3) Uiso 1 1 d D . . . .
C18 C 0.87022(17) 0.3478(4) 0.9626(2) 0.0284(7) Uani 1 1 d . . . . .
N19 N 0.80964(14) 0.4163(3) 0.99065(19) 0.0294(6) Uani 1 1 d . . . . .
C20 C 0.82610(16) 0.4263(4) 1.0998(2) 0.0279(7) Uani 1 1 d . . . . .
N21 N 0.89697(13) 0.3733(3) 1.18043(18) 0.0287(6) Uani 1 1 d . . . . .
C22 C 0.95598(16) 0.3084(4) 1.1479(2) 0.0286(7) Uani 1 1 d . . . . .
N23 N 0.86004(19) 0.3306(5) 0.8581(2) 0.0435(8) Uani 1 1 d . . . . .
N24 N 0.76716(18) 0.4944(4) 1.1314(3) 0.0396(7) Uani 1 1 d . . . . .
N25 N 1.02802(16) 0.2556(4) 1.2198(2) 0.0422(8) Uani 1 1 d . . . . .
H23A H 0.813(2) 0.359(5) 0.805(3) 0.048(10) Uiso 1 1 d . . . . .
H25B H 1.0343(17) 0.261(4) 1.288(3) 0.032(9) Uiso 1 1 d . . . . .
H24A H 0.7802(19) 0.508(4) 1.196(3) 0.033(10) Uiso 1 1 d . . . . .
H23B H 0.898(2) 0.266(5) 0.843(3) 0.060(12) Uiso 1 1 d . . . . .
H25A H 1.068(2) 0.213(6) 1.195(3) 0.072(13) Uiso 1 1 d . . . . .
H24B H 0.719(3) 0.509(6) 1.078(3) 0.075(13) Uiso 1 1 d . . . . .
O26 O 0.48486(15) 0.5980(4) 0.3828(2) 0.0514(7) Uani 1 1 d 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
O1 C3 1.232(4) . ?
O2 C3 1.221(4) . ?
C3 C4 1.509(4) . ?
C4 C5 1.304(4) . ?
C4 H4 0.9500 . ?
C5 N9 1.474(4) . ?
C5 C6 1.529(4) . ?
C6 O8 1.230(4) . ?
C6 O7 1.249(4) . ?
N9 C14 1.342(4) . ?
N9 C10 1.344(4) . ?
C10 C11 1.364(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.372(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(5) . ?
C12 C15 1.447(4) . ?
C13 C14 1.368(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 N16 1.134(4) . ?
N17 C18 1.363(4) . ?
N17 C22 1.363(4) . ?
N17 H17 0.88(3) . ?
C18 N23 1.317(4) . ?
C18 N19 1.321(4) . ?
N19 C20 1.349(4) . ?
C20 N24 1.322(4) . ?
C20 N21 1.346(3) . ?
N21 C22 1.322(3) . ?
C22 N25 1.311(4) . ?
N23 H23A 0.88(3) . ?
N23 H23B 0.88(4) . ?
N24 H24A 0.79(3) . ?
N24 H24B 0.87(4) . ?
N25 H25B 0.85(3) . ?
N25 H25A 0.91(4) . ?
O26 H26B 1.05(5) . ?
O26 H26A 1.07(4) . ?

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
O2 C3 O1 124.9(3) . . ?
O2 C3 C4 116.3(3) . . ?
O1 C3 C4 118.8(3) . . ?
C5 C4 C3 126.4(3) . . ?
C5 C4 H4 116.8 . . ?
C3 C4 H4 116.8 . . ?
C4 C5 N9 119.1(3) . . ?
C4 C5 C6 127.3(3) . . ?
N9 C5 C6 113.6(3) . . ?
O8 C6 O7 127.1(3) . . ?
O8 C6 C5 114.1(3) . . ?
O7 C6 C5 118.8(3) . . ?
C14 N9 C10 121.7(3) . . ?
C14 N9 C5 120.2(2) . . ?
C10 N9 C5 118.1(3) . . ?
N9 C10 C11 119.7(3) . . ?
N9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 119.8(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C11 C12 C15 120.9(3) . . ?
C13 C12 C15 119.2(3) . . ?
C14 C13 C12 118.7(3) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
N9 C14 C13 120.2(3) . . ?
N9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
N16 C15 C12 176.9(4) . . ?
C18 N17 C22 118.9(2) . . ?
C18 N17 H17 118(2) . . ?
C22 N17 H17 124(2) . . ?
N23 C18 N19 120.1(3) . . ?
N23 C18 N17 117.9(3) . . ?
N19 C18 N17 122.0(3) . . ?
C18 N19 C20 115.3(2) . . ?
N24 C20 N21 116.3(3) . . ?
N24 C20 N19 117.3(3) . . ?
N21 C20 N19 126.4(3) . . ?
C22 N21 C20 115.8(2) . . ?
N25 C22 N21 120.8(3) . . ?
N25 C22 N17 117.6(3) . . ?
N21 C22 N17 121.6(3) . . ?
C18 N23 H23A 122(2) . . ?
C18 N23 H23B 116(2) . . ?
H23A N23 H23B 120(3) . . ?
C20 N24 H24A 115(2) . . ?
C20 N24 H24B 115(3) . . ?
H24A N24 H24B 130(4) . . ?
C22 N25 H25B 117(2) . . ?
C22 N25 H25A 119(2) . . ?
H25B N25 H25A 124(3) . . ?
H26B O26 H26A 106(4) . . ?

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
O2 C3 C4 C5 157.3(4) . . . . ?
O1 C3 C4 C5 -26.1(6) . . . . ?
C3 C4 C5 N9 -2.3(5) . . . . ?
C3 C4 C5 C6 178.1(3) . . . . ?
C4 C5 C6 O8 167.3(3) . . . . ?
N9 C5 C6 O8 -12.3(4) . . . . ?
C4 C5 C6 O7 -13.4(5) . . . . ?
N9 C5 C6 O7 167.0(3) . . . . ?
C4 C5 N9 C14 -75.5(4) . . . . ?
C6 C5 N9 C14 104.2(3) . . . . ?
C4 C5 N9 C10 106.2(4) . . . . ?
C6 C5 N9 C10 -74.1(3) . . . . ?
C14 N9 C10 C11 3.1(4) . . . . ?
C5 N9 C10 C11 -178.6(3) . . . . ?
N9 C10 C11 C12 -1.5(5) . . . . ?
C10 C11 C12 C13 -1.3(5) . . . . ?
C10 C11 C12 C15 175.2(3) . . . . ?
C11 C12 C13 C14 2.5(5) . . . . ?
C15 C12 C13 C14 -174.0(3) . . . . ?
C10 N9 C14 C13 -1.9(4) . . . . ?
C5 N9 C14 C13 179.9(3) . . . . ?
C12 C13 C14 N9 -1.0(5) . . . . ?
C22 N17 C18 N23 -179.4(3) . . . . ?
C22 N17 C18 N19 0.8(4) . . . . ?
N23 C18 N19 C20 179.4(3) . . . . ?
N17 C18 N19 C20 -0.8(4) . . . . ?
C18 N19 C20 N24 179.9(3) . . . . ?
C18 N19 C20 N21 -0.2(4) . . . . ?
N24 C20 N21 C22 -178.9(3) . . . . ?
N19 C20 N21 C22 1.2(4) . . . . ?
C20 N21 C22 N25 178.9(3) . . . . ?
C20 N21 C22 N17 -1.2(4) . . . . ?
C18 N17 C22 N25 -179.8(3) . . . . ?
C18 N17 C22 N21 0.3(4) . . . . ?

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
N17 H17 O7 0.88(3) 1.93(3) 2.814(4) 173(3) 2_746
O26 H26A O1 1.07(4) 1.68(4) 2.736(4) 171(6) .
N23 H23A O2 0.88(3) 1.85(4) 2.731(4) 175(3) .
N25 H25A O8 0.91(4) 1.86(4) 2.774(4) 176(4) 2_746

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.065

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

data_Zwitterion2
_database_code_depnum_ccdc_archive 'CCDC 1584661'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
(Z)-4-carbamoyl-1-(3-carboxy-1,1-dihydroxyprop-2-en-1-ide-2-yl)
pyridin-1-ium
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2 O5, H2 O'
_chemical_formula_sum            'C10 H10 N2 O6'
_chemical_formula_weight         254.20

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'

_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                   7.2047(11)
_cell_length_b                   7.5455(11)
_cell_length_c                   10.8058(16)
_cell_angle_alpha                91.800(2)
_cell_angle_beta                 100.509(2)
_cell_angle_gamma                115.757(2)
_cell_volume                     516.12(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3743
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.39

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_F_000             264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.989
_exptl_crystal_size_mid          0.332
_exptl_crystal_size_min          0.092
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9527
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'INCOATEC I\ms HB'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX SMART CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            6006
_diffrn_reflns_av_unetI/netI     0.0134
_diffrn_reflns_av_R_equivalents  0.0113
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.932
_diffrn_reflns_theta_max         27.396
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2301
_reflns_number_gt                2115
_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       'APEX3 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0441P)²+0.2679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2301
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_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
O1 O 0.33856(14) 0.89889(12) 0.85540(8) 0.01499(19) Uani 1 1 d . . . . .
H1 H 0.312(3) 1.008(3) 0.8658(19) 0.047(6) Uiso 1 1 d . . . . .
O2 O 0.11998(16) 0.76536(13) 0.98622(9) 0.0223(2) Uani 1 1 d . . . . .
C3 C 0.23290(18) 0.75581(17) 0.91854(11) 0.0131(2) Uani 1 1 d . . . . .
C4 C 0.26226(18) 0.57222(17) 0.90156(11) 0.0127(2) Uani 1 1 d . . . . .
H4 H 0.187979 0.467965 0.947146 0.015 Uiso 1 1 calc R U . . .
C5 C 0.37824(18) 0.53571(16) 0.83131(10) 0.0111(2) Uani 1 1 d . . . . .
C6 C 0.38696(17) 0.33813(16) 0.81720(10) 0.0108(2) Uani 1 1 d . . . . .
O7 O 0.28822(13) 0.21199(12) 0.88432(8) 0.01264(19) Uani 1 1 d . . . . .
O8 O 0.48806(13) 0.31738(12) 0.74022(8) 0.01510(19) Uani 1 1 d . . . . .
N9 N 0.50414(15) 0.67979(14) 0.75672(9) 0.0101(2) Uani 1 1 d . . . . .
C10 C 0.68255(18) 0.83939(17) 0.81596(11) 0.0124(2) Uani 1 1 d . . . . .
H10 H 0.727828 0.855445 0.905607 0.015 Uiso 1 1 calc R U . . .
C11 C 0.79897(18) 0.97909(17) 0.74603(11) 0.0124(2) Uani 1 1 d . . . . .
H11 H 0.922585 1.093735 0.787460 0.015 Uiso 1 1 calc R U . . .
C12 C 0.73475(17) 0.95157(16) 0.61457(11) 0.0099(2) Uani 1 1 d . . . . .
C13 C 0.55299(18) 0.78174(16) 0.55583(11) 0.0110(2) Uani 1 1 d . . . . .
H13 H 0.508586 0.759101 0.466007 0.013 Uiso 1 1 calc R U . . .
C14 C 0.43840(18) 0.64720(16) 0.62893(11) 0.0109(2) Uani 1 1 d . . . . .
H14 H 0.313616 0.531894 0.589778 0.013 Uiso 1 1 calc R U . . .
C15 C 0.86515(17) 1.11200(16) 0.54293(11) 0.0108(2) Uani 1 1 d . . . . .
O16 O 1.00037(13) 1.27158(12) 0.60362(8) 0.01493(19) Uani 1 1 d . . . . .
N17 N 0.82745(16) 1.07498(14) 0.41755(9) 0.0123(2) Uani 1 1 d . . . . .
H17A H 0.900485 1.166448 0.373635 0.015 Uiso 1 1 calc R U . . .
H17B H 0.729444 0.958987 0.378381 0.015 Uiso 1 1 calc R U . . .
O18 O 0.88331(15) 0.56361(14) 0.67451(9) 0.0201(2) Uani 1 1 d . . . . .
H18A H 0.929(3) 0.475(3) 0.661(2) 0.045(6) Uiso 1 1 d . . . . .
H18B H 0.775(4) 0.499(3) 0.709(2) 0.050(6) 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
O1 C3 1.3161(14) . ?
O1 H1 0.93(2) . ?
O2 C3 1.2110(15) . ?
C3 C4 1.5001(16) . ?
C4 C5 1.3299(16) . ?
C4 H4 0.9500 . ?
C5 N9 1.4557(14) . ?
C5 C6 1.5233(15) . ?
C6 O8 1.2485(14) . ?
C6 O7 1.2575(14) . ?
N9 C10 1.3485(15) . ?
N9 C14 1.3529(15) . ?
C10 C11 1.3779(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.3905(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3954(16) . ?
C12 C15 1.5109(15) . ?
C13 C14 1.3770(15) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O16 1.2356(14) . ?
C15 N17 1.3279(15) . ?
N17 H17A 0.8800 . ?
N17 H17B 0.8800 . ?
O18 H18A 0.88(2) . ?
O18 H18B 0.88(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 O1 H1 112.0(13) . . ?
O2 C3 O1 124.76(11) . . ?
O2 C3 C4 120.63(10) . . ?
O1 C3 C4 114.61(10) . . ?
C5 C4 C3 128.75(11) . . ?
C5 C4 H4 115.6 . . ?
C3 C4 H4 115.6 . . ?
C4 C5 N9 122.90(10) . . ?
C4 C5 C6 123.66(10) . . ?
N9 C5 C6 113.41(9) . . ?
O8 C6 O7 127.01(10) . . ?
O8 C6 C5 117.30(10) . . ?
O7 C6 C5 115.68(10) . . ?
C10 N9 C14 122.03(10) . . ?
C10 N9 C5 119.58(9) . . ?
C14 N9 C5 118.39(9) . . ?
N9 C10 C11 119.78(10) . . ?
N9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 119.72(10) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 119.10(10) . . ?
C11 C12 C15 117.46(10) . . ?
C13 C12 C15 123.43(10) . . ?
C14 C13 C12 119.56(10) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
N9 C14 C13 119.76(10) . . ?
N9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
O16 C15 N17 123.22(10) . . ?
O16 C15 C12 118.49(10) . . ?
N17 C15 C12 118.29(10) . . ?
C15 N17 H17A 120.0 . . ?
C15 N17 H17B 120.0 . . ?
H17A N17 H17B 120.0 . . ?
H18A O18 H18B 103.1(19) . . ?

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
O2 C3 C4 C5 179.69(12) . . . . ?
O1 C3 C4 C5 -0.53(18) . . . . ?
C3 C4 C5 N9 0.79(19) . . . . ?
C3 C4 C5 C6 -177.05(10) . . . . ?
C4 C5 C6 O8 174.19(11) . . . . ?
N9 C5 C6 O8 -3.84(14) . . . . ?
C4 C5 C6 O7 -5.05(17) . . . . ?
N9 C5 C6 O7 176.92(9) . . . . ?
C4 C5 N9 C10 72.53(15) . . . . ?
C6 C5 N9 C10 -109.43(11) . . . . ?
C4 C5 N9 C14 -108.20(13) . . . . ?
C6 C5 N9 C14 69.84(13) . . . . ?
C14 N9 C10 C11 2.63(17) . . . . ?
C5 N9 C10 C11 -178.13(10) . . . . ?
N9 C10 C11 C12 -1.81(17) . . . . ?
C10 C11 C12 C13 -0.18(17) . . . . ?
C10 C11 C12 C15 178.45(10) . . . . ?
C11 C12 C13 C14 1.41(16) . . . . ?
C15 C12 C13 C14 -177.13(10) . . . . ?
C10 N9 C14 C13 -1.37(16) . . . . ?
C5 N9 C14 C13 179.37(10) . . . . ?
C12 C13 C14 N9 -0.68(16) . . . . ?
C11 C12 C15 O16 -11.15(15) . . . . ?
C13 C12 C15 O16 167.41(10) . . . . ?
C11 C12 C15 N17 169.40(10) . . . . ?
C13 C12 C15 N17 -12.04(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O7 0.93(2) 1.63(2) 2.5593(12) 175(2) 1_565

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_1Melamine
_database_code_depnum_ccdc_archive 'CCDC 1584663'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
1,3,5-triazine-2,4,6-triamine (Z)-2-(3-carbamoylpyridin-1-ium-1-yl)
-1,1-dihydroxybut-2-en-1-ideoate dihydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H7 N2 O5, C3 H7 N6, 2(H2 O)'
_chemical_formula_sum            'C13 H18 N8 O7'
_chemical_formula_weight         398.35

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                   5.7312(5)
_cell_length_b                   12.3326(10)
_cell_length_c                   12.8974(11)
_cell_angle_alpha                71.530(2)
_cell_angle_beta                 86.574(3)
_cell_angle_gamma                89.673(3)
_cell_volume                     863.01(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3835
_cell_measurement_theta_min      3.24
_cell_measurement_theta_max      28.68

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    0.126
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9481
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS, 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'INCOATEC I\ms HB'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX SMART CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            12027
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.767
_diffrn_reflns_theta_max         28.806
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4460
_reflns_number_gt                3311
_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       'APEX3 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0288P)²+1.2353P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4460
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.1448
_refine_ls_wR_factor_gt          0.1331
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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
O1 O 0.3000(5) 0.50375(17) 0.9056(2) 0.0556(7) Uani 1 1 d . . . . .
H30B H 0.702(8) 0.636(4) 0.974(4) 0.084(15) Uiso 1 1 d . . . . .
H30A H 0.546(7) 0.688(3) 0.900(3) 0.057(11) Uiso 1 1 d . . . . .
H29B H 0.654(8) 0.392(3) 0.463(3) 0.069(14) Uiso 1 1 d . . . . .
H29A H 0.742(6) 0.429(3) 0.541(3) 0.055(11) Uiso 1 1 d . . . . .
O2 O 0.2538(4) 0.68858(15) 0.83302(15) 0.0347(5) Uani 1 1 d . . . . .
C3 C 0.1986(5) 0.5873(2) 0.8472(2) 0.0287(6) Uani 1 1 d . . . . .
C4 C -0.0058(9) 0.6056(4) 0.7709(4) 0.0198(14) Uani 0.516(9) 1 d . . P A 2
H4 H -0.047528 0.681869 0.732846 0.024 Uiso 0.516(9) 1 calc R U P A 2
C5 C -0.1259(8) 0.5217(4) 0.7554(3) 0.0144(13) Uani 0.516(9) 1 d . . P A 2
C6 C -0.3300(4) 0.5497(2) 0.67942(19) 0.0222(5) Uani 1 1 d . . . . .
O7 O -0.3832(4) 0.45434(15) 0.67429(18) 0.0418(5) Uani 1 1 d . . . . .
O8 O -0.4227(4) 0.64111(15) 0.63211(16) 0.0379(5) Uani 1 1 d . . . . .
C9 C -0.1403(9) 0.5954(5) 0.7351(4) 0.0180(15) Uani 0.484(9) 1 d . . P A 1
H9 H -0.129009 0.675716 0.720488 0.022 Uiso 0.484(9) 1 calc R U P A 1
C10 C 0.0068(8) 0.5310(5) 0.8014(4) 0.0160(15) Uani 0.484(9) 1 d . . P A 1
N11 N -0.0444(5) 0.40306(18) 0.8239(2) 0.0431(7) Uani 1 1 d . . . . .
C12 C -0.2052(5) 0.3489(2) 0.9025(2) 0.0239(5) Uani 1 1 d . . . . .
H12 H -0.324322 0.390540 0.926922 0.029 Uiso 1 1 calc R U . . .
C13 C -0.1958(5) 0.2322(2) 0.9472(2) 0.0269(6) Uani 1 1 d . . . . .
H13 H -0.309464 0.192067 1.002493 0.032 Uiso 1 1 calc R U . . .
C14 C -0.0191(5) 0.1737(2) 0.9111(2) 0.0266(6) Uani 1 1 d . . . . .
H14 H -0.011729 0.092899 0.941937 0.032 Uiso 1 1 calc R U . . .
C15 C 0.1469(4) 0.23143(19) 0.83052(19) 0.0195(5) Uani 1 1 d . . . . .
C16 C 0.1296(6) 0.3478(2) 0.7868(3) 0.0418(8) Uani 1 1 d . . . . .
H16 H 0.239758 0.389524 0.730581 0.050 Uiso 1 1 calc R U . . .
C17 C 0.3395(4) 0.1633(2) 0.7955(2) 0.0220(5) Uani 1 1 d . . . . .
O18 O 0.3361(3) 0.05768(14) 0.83816(16) 0.0298(4) Uani 1 1 d . . . . .
N19 N 0.5034(4) 0.21945(18) 0.72117(18) 0.0268(5) Uani 1 1 d . . . . .
H19A H 0.617181 0.181772 0.699711 0.032 Uiso 1 1 calc R U . . .
H19B H 0.498257 0.294377 0.693316 0.032 Uiso 1 1 calc R U . . .
N20 N 0.0861(4) 0.89855(17) 0.72183(17) 0.0217(4) Uani 1 1 d . . . . .
C21 C -0.0869(4) 0.96984(19) 0.73669(19) 0.0207(5) Uani 1 1 d . . . . .
N22 N -0.1005(4) 1.07663(16) 0.67013(16) 0.0199(4) Uani 1 1 d . . . . .
C23 C 0.0721(4) 1.11083(19) 0.58946(19) 0.0201(5) Uani 1 1 d . . . . .
N24 N 0.2485(4) 1.04497(16) 0.56927(16) 0.0216(4) Uani 1 1 d . . . . .
C25 C 0.2506(4) 0.93812(19) 0.63685(19) 0.0217(5) Uani 1 1 d . . . . .
N26 N 0.4156(4) 0.86772(17) 0.62275(18) 0.0279(5) Uani 1 1 d . . . . .
H26A H 0.523534 0.891620 0.568780 0.034 Uiso 1 1 calc R U . . .
H26B H 0.417472 0.796995 0.667347 0.034 Uiso 1 1 calc R U . . .
N27 N -0.2406(4) 0.93031(17) 0.82103(17) 0.0246(5) Uani 1 1 d . . . . .
H27A H -0.352362 0.974749 0.833257 0.030 Uiso 1 1 calc R U . . .
H27B H -0.230957 0.859587 0.864900 0.030 Uiso 1 1 calc R U . . .
N28 N 0.0712(4) 1.21822(16) 0.52451(17) 0.0255(5) Uani 1 1 d . . . . .
H28A H 0.181223 1.243312 0.471700 0.031 Uiso 1 1 calc R U . . .
H28B H -0.039368 1.264506 0.534145 0.031 Uiso 1 1 calc R U . . .
O29 O 0.7920(5) 0.4091(2) 0.4824(2) 0.0497(6) Uani 1 1 d . . . . .
O30 O 0.6768(4) 0.70006(16) 0.92901(17) 0.0287(4) Uani 1 1 d . . . . .
H1 H 0.102(5) 0.831(3) 0.763(3) 0.038(9) 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
O1 C3 1.233(3) . ?
O2 C3 1.243(3) . ?
C3 C4 1.545(6) . ?
C3 C10 1.545(5) . ?
C4 C5 1.319(8) . ?
C4 H4 0.9500 . ?
C5 N11 1.537(5) . ?
C5 C6 1.538(5) . ?
C6 O8 1.233(3) . ?
C6 O7 1.240(3) . ?
C6 C9 1.540(6) . ?
C9 C10 1.311(8) . ?
C9 H9 0.9500 . ?
C10 N11 1.538(6) . ?
N11 C12 1.338(3) . ?
N11 C16 1.353(3) . ?
C12 C13 1.372(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.371(3) . ?
C15 C17 1.516(3) . ?
C16 H16 0.9500 . ?
C17 O18 1.243(3) . ?
C17 N19 1.327(3) . ?
N19 H19A 0.8800 . ?
N19 H19B 0.8800 . ?
N20 C21 1.366(3) . ?
N20 C25 1.368(3) . ?
N20 H1 0.84(3) . ?
C21 N27 1.323(3) . ?
C21 N22 1.330(3) . ?
N22 C23 1.358(3) . ?
C23 N28 1.324(3) . ?
C23 N24 1.357(3) . ?
N24 C25 1.330(3) . ?
C25 N26 1.323(3) . ?
N26 H26A 0.8800 . ?
N26 H26B 0.8800 . ?
N27 H27A 0.8800 . ?
N27 H27B 0.8800 . ?
N28 H28A 0.8800 . ?
N28 H28B 0.8800 . ?
O29 H29B 0.89(4) . ?
O29 H29A 0.90(4) . ?
O30 H30B 0.84(5) . ?
O30 H30A 0.89(4) . ?

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
O1 C3 O2 124.8(3) . . ?
O1 C3 C4 135.4(3) . . ?
O2 C3 C4 99.8(3) . . ?
O1 C3 C10 102.3(3) . . ?
O2 C3 C10 132.9(3) . . ?
C5 C4 C3 124.0(5) . . ?
C5 C4 H4 118.0 . . ?
C3 C4 H4 118.0 . . ?
C4 C5 N11 112.6(4) . . ?
C4 C5 C6 119.6(5) . . ?
N11 C5 C6 127.7(4) . . ?
O8 C6 O7 126.3(2) . . ?
O8 C6 C5 131.5(3) . . ?
O7 C6 C5 102.2(3) . . ?
O8 C6 C9 98.8(3) . . ?
O7 C6 C9 134.9(3) . . ?
C10 C9 C6 124.5(5) . . ?
C10 C9 H9 117.7 . . ?
C6 C9 H9 117.7 . . ?
C9 C10 N11 111.7(4) . . ?
C9 C10 C3 119.7(5) . . ?
N11 C10 C3 128.6(4) . . ?
C12 N11 C16 122.8(2) . . ?
C12 N11 C5 112.0(3) . . ?
C16 N11 C5 122.0(3) . . ?
C12 N11 C10 120.0(3) . . ?
C16 N11 C10 113.8(3) . . ?
N11 C12 C13 119.1(2) . . ?
N11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C14 119.4(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C15 120.7(2) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 118.2(2) . . ?
C16 C15 C17 123.3(2) . . ?
C14 C15 C17 118.5(2) . . ?
N11 C16 C15 119.9(2) . . ?
N11 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
O18 C17 N19 123.3(2) . . ?
O18 C17 C15 118.3(2) . . ?
N19 C17 C15 118.3(2) . . ?
C17 N19 H19A 120.0 . . ?
C17 N19 H19B 120.0 . . ?
H19A N19 H19B 120.0 . . ?
C21 N20 C25 119.3(2) . . ?
C21 N20 H1 124(2) . . ?
C25 N20 H1 117(2) . . ?
N27 C21 N22 120.3(2) . . ?
N27 C21 N20 118.1(2) . . ?
N22 C21 N20 121.7(2) . . ?
C21 N22 C23 115.7(2) . . ?
N28 C23 N24 116.4(2) . . ?
N28 C23 N22 117.7(2) . . ?
N24 C23 N22 125.9(2) . . ?
C25 N24 C23 115.8(2) . . ?
N26 C25 N24 119.8(2) . . ?
N26 C25 N20 118.6(2) . . ?
N24 C25 N20 121.6(2) . . ?
C25 N26 H26A 120.0 . . ?
C25 N26 H26B 120.0 . . ?
H26A N26 H26B 120.0 . . ?
C21 N27 H27A 120.0 . . ?
C21 N27 H27B 120.0 . . ?
H27A N27 H27B 120.0 . . ?
C23 N28 H28A 120.0 . . ?
C23 N28 H28B 120.0 . . ?
H28A N28 H28B 120.0 . . ?
H29B O29 H29A 98(4) . . ?
H30B O30 H30A 103(4) . . ?

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 C3 C4 C5 1.7(7) . . . . ?
O2 C3 C4 C5 179.1(4) . . . . ?
C3 C4 C5 N11 1.4(6) . . . . ?
C3 C4 C5 C6 178.6(3) . . . . ?
C4 C5 C6 O8 -6.3(6) . . . . ?
N11 C5 C6 O8 170.4(3) . . . . ?
C4 C5 C6 O7 172.8(4) . . . . ?
N11 C5 C6 O7 -10.5(4) . . . . ?
O8 C6 C9 C10 177.1(4) . . . . ?
O7 C6 C9 C10 -5.5(7) . . . . ?
C6 C9 C10 N11 -4.3(6) . . . . ?
C6 C9 C10 C3 176.6(3) . . . . ?
O1 C3 C10 C9 179.4(4) . . . . ?
O2 C3 C10 C9 -1.8(6) . . . . ?
O1 C3 C10 N11 0.4(5) . . . . ?
O2 C3 C10 N11 179.2(3) . . . . ?
C4 C5 N11 C12 111.6(4) . . . . ?
C6 C5 N11 C12 -65.3(4) . . . . ?
C4 C5 N11 C16 -88.2(5) . . . . ?
C6 C5 N11 C16 94.9(5) . . . . ?
C9 C10 N11 C12 -84.5(5) . . . . ?
C3 C10 N11 C12 94.6(5) . . . . ?
C9 C10 N11 C16 116.1(4) . . . . ?
C3 C10 N11 C16 -64.9(5) . . . . ?
C16 N11 C12 C13 -0.5(5) . . . . ?
C5 N11 C12 C13 159.5(3) . . . . ?
C10 N11 C12 C13 -158.0(3) . . . . ?
N11 C12 C13 C14 0.7(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C13 C14 C15 C17 178.8(2) . . . . ?
C12 N11 C16 C15 -0.4(5) . . . . ?
C5 N11 C16 C15 -158.4(3) . . . . ?
C10 N11 C16 C15 158.4(3) . . . . ?
C14 C15 C16 N11 1.0(5) . . . . ?
C17 C15 C16 N11 -178.6(3) . . . . ?
C16 C15 C17 O18 -178.2(3) . . . . ?
C14 C15 C17 O18 2.3(3) . . . . ?
C16 C15 C17 N19 2.0(4) . . . . ?
C14 C15 C17 N19 -177.5(2) . . . . ?
C25 N20 C21 N27 -178.4(2) . . . . ?
C25 N20 C21 N22 0.5(4) . . . . ?
N27 C21 N22 C23 176.7(2) . . . . ?
N20 C21 N22 C23 -2.2(3) . . . . ?
C21 N22 C23 N28 -176.9(2) . . . . ?
C21 N22 C23 N24 2.6(4) . . . . ?
N28 C23 N24 C25 178.4(2) . . . . ?
N22 C23 N24 C25 -1.2(4) . . . . ?
C23 N24 C25 N26 179.6(2) . . . . ?
C23 N24 C25 N20 -0.7(3) . . . . ?
C21 N20 C25 N26 -179.3(2) . . . . ?
C21 N20 C25 N24 1.0(4) . . . . ?

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
O30 H30A O1 0.89(4) 2.66(4) 3.349(3) 135(3) .
O30 H30A O2 0.89(4) 1.93(4) 2.811(3) 170(3) .
O29 H29B O8 0.89(4) 1.99(4) 2.830(4) 158(4) 2_566
O29 H29A O7 0.90(4) 1.94(4) 2.832(3) 173(3) 1_655
N19 H19B O7 0.88 2.03 2.836(3) 152.7 1_655
N26 H26A N24 0.88 2.08 2.960(3) 174.2 2_676
N26 H26B O8 0.88 2.29 2.907(3) 127.6 1_655
N27 H27A O18 0.88 2.06 2.918(3) 164.6 1_465
N27 H27B O30 0.88 1.94 2.767(3) 156.1 1_455
N28 H28A O8 0.88 2.08 2.912(3) 157.1 2_576
N28 H28B O29 0.88 1.97 2.765(3) 150.5 1_465
N20 H1 O2 0.84(3) 1.93(3) 2.733(3) 158(3) .

_refine_diff_density_max         0.628
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_2Melamine
_database_code_depnum_ccdc_archive 'CCDC 1584664'
_audit_update_record             
;
2017-11-28 deposited with the CCDC.
2017-11-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
1,3,5-triazine-2,4,6-triamine (Z)-2-(4-carbamoylpyridin-1-ium-1-yl)
-1,1-dihydroxybut-2-en-1-ideoate dihydrate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H7 N2 O5, C3 H7 N6, H2 O'
_chemical_formula_sum            'C13 H16 N8 O6'
_chemical_formula_weight         380.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   8.6886(3)
_cell_length_b                   8.9638(3)
_cell_length_c                   11.2137(4)
_cell_angle_alpha                94.473(2)
_cell_angle_beta                 103.931(2)
_cell_angle_gamma                106.6570(10)
_cell_volume                     801.88(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5896
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.80

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.208
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.081
_exptl_absorpt_coefficient_mu    0.128
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9382
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS (Bruker, 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?

_diffrn_source_type              'INCOATEC I\ms HB'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_measurement_device_type  'Bruker APEX SMART CCD area-detector'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_type            'Bruker APEX II'

_diffrn_reflns_number            10818
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.402
_diffrn_reflns_theta_max         28.871
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4114
_reflns_number_gt                3483
_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       'APEX3 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
'X-seed (Barbour, 2001; Atwood & barbour, 2003)'
_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)+(0.0359P)²+0.6200P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4114
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0996
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
O1 O 0.51760(14) 0.82002(14) 0.59331(11) 0.0205(3) Uani 1 1 d . . . . .
O2 O 0.76800(14) 0.83253(13) 0.71387(10) 0.0174(2) Uani 1 1 d . . . . .
C3 C 0.63785(19) 0.87283(18) 0.68818(14) 0.0134(3) Uani 1 1 d . . . . .
C4 C 0.6380(2) 1.00170(18) 0.78560(14) 0.0153(3) Uani 1 1 d . . . . .
H4 H 0.743193 1.059836 0.841802 0.018 Uiso 1 1 calc R U . . .
C5 C 0.50695(19) 1.04126(17) 0.80022(14) 0.0132(3) Uani 1 1 d . . . . .
C6 C 0.51176(19) 1.16432(17) 0.90366(13) 0.0129(3) Uani 1 1 d . . . . .
O7 O 0.65157(13) 1.24789(13) 0.97205(10) 0.0144(2) Uani 1 1 d . . . . .
O8 O 0.37141(14) 1.16932(14) 0.91167(11) 0.0194(3) Uani 1 1 d . . . . .
N9 N 0.34201(15) 0.95726(15) 0.71592(11) 0.0116(2) Uani 1 1 d . . . . .
C10 C 0.30147(19) 0.99120(17) 0.59966(14) 0.0130(3) Uani 1 1 d . . . . .
H10 H 0.375265 1.076418 0.575554 0.016 Uiso 1 1 calc R U . . .
C11 C 0.15261(18) 0.90184(17) 0.51588(14) 0.0127(3) Uani 1 1 d . . . . .
H11 H 0.122996 0.924912 0.433791 0.015 Uiso 1 1 calc R U . . .
C12 C 0.04627(18) 0.77749(17) 0.55292(13) 0.0117(3) Uani 1 1 d . . . . .
C13 C 0.08824(19) 0.74812(17) 0.67455(14) 0.0130(3) Uani 1 1 d . . . . .
H13 H 0.014339 0.666322 0.701772 0.016 Uiso 1 1 calc R U . . .
C14 C 0.23877(19) 0.83963(17) 0.75489(14) 0.0127(3) Uani 1 1 d . . . . .
H14 H 0.270079 0.819988 0.837893 0.015 Uiso 1 1 calc R U . . .
C15 C -0.10999(19) 0.67338(17) 0.45783(14) 0.0128(3) Uani 1 1 d . . . . .
O16 O -0.09526(14) 0.61071(13) 0.36014(10) 0.0175(2) Uani 1 1 d . . . . .
N17 N -0.25176(16) 0.65803(16) 0.48679(12) 0.0157(3) Uani 1 1 d . . . . .
H17A H -0.347008 0.599097 0.434601 0.019 Uiso 1 1 calc R U . . .
H17B H -0.250974 0.706744 0.558277 0.019 Uiso 1 1 calc R U . . .
N18 N 0.31551(16) 0.37741(15) 0.07948(12) 0.0120(3) Uani 1 1 d . . . . .
H18 H 0.327(2) 0.313(2) 0.0214(19) 0.020(5) Uiso 1 1 d . . . . .
C19 C 0.16160(18) 0.38531(17) 0.08296(14) 0.0125(3) Uani 1 1 d . . . . .
N20 N 0.14319(16) 0.47626(15) 0.17388(12) 0.0130(3) Uani 1 1 d . . . . .
C21 C 0.28409(19) 0.55595(16) 0.26391(14) 0.0119(3) Uani 1 1 d . . . . .
N22 N 0.44104(16) 0.55355(15) 0.26852(11) 0.0123(3) Uani 1 1 d . . . . .
C23 C 0.45268(18) 0.46295(17) 0.17325(13) 0.0117(3) Uani 1 1 d . . . . .
N24 N 0.59961(16) 0.45282(16) 0.16602(12) 0.0148(3) Uani 1 1 d . . . . .
H24A H 0.691062 0.506365 0.224629 0.018 Uiso 1 1 calc R U . . .
H24B H 0.605631 0.392559 0.102602 0.018 Uiso 1 1 calc R U . . .
N25 N 0.02950(17) 0.29939(16) -0.00760(13) 0.0177(3) Uani 1 1 d . . . . .
H25A H -0.070714 0.302661 -0.007436 0.021 Uiso 1 1 calc R U . . .
H25B H 0.041883 0.238990 -0.067977 0.021 Uiso 1 1 calc R U . . .
N26 N 0.26523(17) 0.64555(15) 0.35652(12) 0.0148(3) Uani 1 1 d . . . . .
H26A H 0.165255 0.649940 0.356254 0.018 Uiso 1 1 calc R U . . .
H26B H 0.352754 0.700301 0.417920 0.018 Uiso 1 1 calc R U . . .
O27 O 0.96086(17) 0.90142(15) 0.21179(12) 0.0217(3) Uani 1 1 d . . . . .
H27B H 0.857(3) 0.902(3) 0.188(2) 0.036(6) Uiso 1 1 d . . . . .
H27A H 1.031(4) 0.998(3) 0.217(3) 0.056(8) 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
O1 C3 1.2451(19) . ?
O2 C3 1.2592(19) . ?
C3 C4 1.526(2) . ?
C4 C5 1.327(2) . ?
C4 H4 0.9500 . ?
C5 N9 1.4602(19) . ?
C5 C6 1.521(2) . ?
C6 O7 1.2510(18) . ?
C6 O8 1.2572(19) . ?
N9 C10 1.3485(19) . ?
N9 C14 1.3512(19) . ?
C10 C11 1.379(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.391(2) . ?
C12 C15 1.508(2) . ?
C13 C14 1.377(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 O16 1.2428(18) . ?
C15 N17 1.3206(19) . ?
N17 H17A 0.8800 . ?
N17 H17B 0.8800 . ?
N18 C23 1.3642(19) . ?
N18 C19 1.3689(19) . ?
N18 H18 0.88(2) . ?
C19 N25 1.3236(19) . ?
C19 N20 1.3241(19) . ?
N20 C21 1.3488(19) . ?
C21 N26 1.3334(18) . ?
C21 N22 1.3587(19) . ?
N22 C23 1.3322(18) . ?
C23 N24 1.3266(19) . ?
N24 H24A 0.8800 . ?
N24 H24B 0.8800 . ?
N25 H25A 0.8800 . ?
N25 H25B 0.8800 . ?
N26 H26A 0.8800 . ?
N26 H26B 0.8800 . ?
O27 H27B 0.88(3) . ?
O27 H27A 0.89(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
O1 C3 O2 126.34(14) . . ?
O1 C3 C4 120.10(13) . . ?
O2 C3 C4 113.55(13) . . ?
C5 C4 C3 126.98(14) . . ?
C5 C4 H4 116.5 . . ?
C3 C4 H4 116.5 . . ?
C4 C5 N9 119.11(13) . . ?
C4 C5 C6 125.05(14) . . ?
N9 C5 C6 115.77(13) . . ?
O7 C6 O8 126.78(14) . . ?
O7 C6 C5 117.98(13) . . ?
O8 C6 C5 115.24(13) . . ?
C10 N9 C14 121.97(13) . . ?
C10 N9 C5 119.61(12) . . ?
C14 N9 C5 118.26(12) . . ?
N9 C10 C11 119.80(14) . . ?
N9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 119.24(13) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 119.88(14) . . ?
C13 C12 C15 121.39(13) . . ?
C11 C12 C15 118.69(13) . . ?
C14 C13 C12 118.88(14) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
N9 C14 C13 120.16(13) . . ?
N9 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
O16 C15 N17 125.88(14) . . ?
O16 C15 C12 118.10(13) . . ?
N17 C15 C12 116.02(13) . . ?
C15 N17 H17A 120.0 . . ?
C15 N17 H17B 120.0 . . ?
H17A N17 H17B 120.0 . . ?
C23 N18 C19 119.14(12) . . ?
C23 N18 H18 119.4(13) . . ?
C19 N18 H18 121.3(13) . . ?
N25 C19 N20 120.08(14) . . ?
N25 C19 N18 118.35(13) . . ?
N20 C19 N18 121.56(13) . . ?
C19 N20 C21 115.90(13) . . ?
N26 C21 N20 115.91(13) . . ?
N26 C21 N22 117.71(13) . . ?
N20 C21 N22 126.37(13) . . ?
C23 N22 C21 115.15(12) . . ?
N24 C23 N22 120.87(13) . . ?
N24 C23 N18 117.27(13) . . ?
N22 C23 N18 121.85(13) . . ?
C23 N24 H24A 120.0 . . ?
C23 N24 H24B 120.0 . . ?
H24A N24 H24B 120.0 . . ?
C19 N25 H25A 120.0 . . ?
C19 N25 H25B 120.0 . . ?
H25A N25 H25B 120.0 . . ?
C21 N26 H26A 120.0 . . ?
C21 N26 H26B 120.0 . . ?
H26A N26 H26B 120.0 . . ?
H27B O27 H27A 110(2) . . ?

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 C3 C4 C5 18.6(2) . . . . ?
O2 C3 C4 C5 -162.71(16) . . . . ?
C3 C4 C5 N9 -0.6(2) . . . . ?
C3 C4 C5 C6 176.20(14) . . . . ?
C4 C5 C6 O7 8.7(2) . . . . ?
N9 C5 C6 O7 -174.44(13) . . . . ?
C4 C5 C6 O8 -170.56(15) . . . . ?
N9 C5 C6 O8 6.33(19) . . . . ?
C4 C5 N9 C10 -76.76(19) . . . . ?
C6 C5 N9 C10 106.15(15) . . . . ?
C4 C5 N9 C14 98.74(17) . . . . ?
C6 C5 N9 C14 -78.35(16) . . . . ?
C14 N9 C10 C11 -1.7(2) . . . . ?
C5 N9 C10 C11 173.64(13) . . . . ?
N9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C13 2.2(2) . . . . ?
C10 C11 C12 C15 -175.57(13) . . . . ?
C11 C12 C13 C14 -2.7(2) . . . . ?
C15 C12 C13 C14 175.03(13) . . . . ?
C10 N9 C14 C13 1.2(2) . . . . ?
C5 N9 C14 C13 -174.19(13) . . . . ?
C12 C13 C14 N9 1.0(2) . . . . ?
C13 C12 C15 O16 -123.36(16) . . . . ?
C11 C12 C15 O16 54.35(19) . . . . ?
C13 C12 C15 N17 56.96(19) . . . . ?
C11 C12 C15 N17 -125.33(15) . . . . ?
C23 N18 C19 N25 -178.81(13) . . . . ?
C23 N18 C19 N20 1.3(2) . . . . ?
N25 C19 N20 C21 178.15(13) . . . . ?
N18 C19 N20 C21 -2.0(2) . . . . ?
C19 N20 C21 N26 -178.95(13) . . . . ?
C19 N20 C21 N22 1.2(2) . . . . ?
N26 C21 N22 C23 -179.57(13) . . . . ?
N20 C21 N22 C23 0.2(2) . . . . ?
C21 N22 C23 N24 178.87(13) . . . . ?
C21 N22 C23 N18 -1.0(2) . . . . ?
C19 N18 C23 N24 -179.59(13) . . . . ?
C19 N18 C23 N22 0.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N17 H17B O2 0.88 1.95 2.8240(17) 174.2 1_455
N18 H18 O8 0.88(2) 1.90(2) 2.7692(17) 172.9(19) 1_544
N24 H24A O16 0.88 2.01 2.8913(17) 174.9 1_655
N24 H24B O7 0.88 2.07 2.9384(16) 171.3 1_544
N25 H25B O27 0.88 1.96 2.8330(18) 172.8 2_665
N26 H26B O1 0.88 2.12 2.9812(17) 165.0 .
O27 H27B O8 0.88(3) 1.92(3) 2.7464(17) 156(2) 2_676
O27 H27A O2 0.89(3) 1.90(3) 2.7305(18) 154(3) 2_776

_refine_diff_density_max         0.438
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.057

