# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_m
_audit_creation_method           SHELXL-97
_chemical_name_common            'Diglycinium squarate'
_chemical_melting_point          'Diglycinium squarate'
_chemical_formula_moiety         'C4 O4, 2(C2 H6 N O2)'
_chemical_formula_sum            'C8 H12 N2 O8'
_chemical_formula_weight         264.20

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  -C2yc

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

_cell_length_a                   16.8392(3)
_cell_length_b                   8.3163(2)
_cell_length_c                   15.8267(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.063(2)
_cell_angle_gamma                90.00
_cell_volume                     2182.27(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.59

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      1.608
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   

; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (1990)).
;
_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10909
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         27.59
_reflns_number_total             2371
_reflns_number_gt                2149
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury (2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1067P)²+3.7054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2371
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   0.697
_refine_ls_restrained_S_all      0.697
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.19863(8) 1.03712(15) 1.28105(7) 0.0277(3) Uani 1 1 d . . .
H1N H 1.2344(11) 1.107(2) 1.2945(11) 0.033 Uiso 1 1 d . . .
H2N H 1.2174(11) 0.960(2) 1.2515(12) 0.033 Uiso 1 1 d . . .
H3N H 1.1884(11) 1.000(2) 1.3309(12) 0.033 Uiso 1 1 d . . .
O5 O 1.09112(7) 1.24170(15) 1.09355(7) 0.0375(3) Uani 1 1 d . . .
H3 H 1.0379(13) 1.205(2) 1.1059(13) 0.045 Uiso 1 1 d . . .
O6 O 1.22020(6) 1.22606(14) 1.14996(7) 0.0373(3) Uani 1 1 d . . .
C5 C 1.15023(8) 1.19718(16) 1.15266(8) 0.0255(3) Uani 1 1 d . . .
C6 C 1.12636(8) 1.10739(18) 1.22758(8) 0.0272(3) Uani 1 1 d . . .
H61 H 1.1020(10) 1.182(2) 1.2636(11) 0.033 Uiso 1 1 d . . .
H62 H 1.0889(11) 1.032(2) 1.2115(11) 0.033 Uiso 1 1 d . . .
O2 O 0.78579(7) 0.98780(14) 1.03533(6) 0.0363(3) Uani 1 1 d . . .
O1 O 0.77536(6) 1.18453(12) 0.85428(6) 0.0306(2) Uani 1 1 d . . .
O3 O 0.95691(7) 1.14066(16) 1.10411(6) 0.0418(3) Uani 1 1 d . . .
C3 C 0.90802(8) 1.15316(17) 1.03405(8) 0.0276(3) Uani 1 1 d . . .
O4 O 0.95128(8) 1.33729(16) 0.92571(7) 0.0479(3) Uani 1 1 d . . .
C1 C 0.82503(8) 1.17282(15) 0.92191(8) 0.0242(3) Uani 1 1 d . . .
C4 C 0.90525(8) 1.24142(17) 0.95416(8) 0.0286(3) Uani 1 1 d . . .
C2 C 0.82952(8) 1.08368(16) 1.00332(8) 0.0253(3) Uani 1 1 d . . .
O6' O 0.90458(7) 1.22915(13) 0.71247(7) 0.0400(3) Uani 1 1 d . . .
O5' O 0.90818(8) 1.46823(15) 0.77763(7) 0.0451(3) Uani 1 1 d . . .
H4 H 0.9205(13) 1.422(3) 0.8226(14) 0.054 Uiso 1 1 d . . .
N1' N 0.85856(9) 1.35701(18) 0.55508(8) 0.0370(3) Uani 1 1 d . . .
H1'N H 0.8415(12) 1.253(3) 0.5720(13) 0.044 Uiso 1 1 d . . .
H2'N H 0.8132(12) 1.392(3) 0.5169(13) 0.044 Uiso 1 1 d . . .
H3'N H 0.8949(13) 1.342(3) 0.5252(14) 0.044 Uiso 1 1 d . . .
C5' C 0.89955(8) 1.37277(17) 0.71066(9) 0.0280(3) Uani 1 1 d . . .
C6' C 0.88149(9) 1.46631(17) 0.62842(9) 0.0301(3) Uani 1 1 d . . .
H61' H 0.9259(12) 1.530(2) 0.6240(12) 0.036 Uiso 1 1 d . . .
H62' H 0.8367(11) 1.536(2) 0.6325(11) 0.036 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 1.4760(17) . ?
O5 C5 1.2951(17) . ?
O6 C5 1.2106(17) . ?
C5 C6 1.5137(17) . ?
O2 C2 1.2510(17) . ?
O1 C1 1.2417(16) . ?
O3 C3 1.2645(17) . ?
C3 C2 1.4468(18) . ?
C3 C4 1.4557(18) . ?
O4 C4 1.2494(18) . ?
C1 C4 1.4731(18) . ?
C1 C2 1.4769(17) . ?
O6' C5' 1.1973(19) . ?
O5' C5' 1.3117(18) . ?
N1' C6' 1.4717(19) . ?
C5' C6' 1.5012(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 C5 O5 123.21(12) . . ?
O6 C5 C6 121.25(12) . . ?
O5 C5 C6 115.54(12) . . ?
N1 C6 C5 109.84(11) . . ?
O3 C3 C2 132.73(13) . . ?
O3 C3 C4 136.07(13) . . ?
C2 C3 C4 91.18(11) . . ?
O1 C1 C4 135.00(12) . . ?
O1 C1 C2 135.68(12) . . ?
C4 C1 C2 89.31(10) . . ?
O4 C4 C3 135.00(13) . . ?
O4 C4 C1 135.34(12) . . ?
C3 C4 C1 89.65(11) . . ?
O2 C2 C3 133.33(12) . . ?
O2 C2 C1 136.82(12) . . ?
C3 C2 C1 89.85(10) . . ?
O6' C5' O5' 125.95(14) . . ?
O6' C5' C6' 122.71(13) . . ?
O5' C5' C6' 111.34(12) . . ?
N1' C6' C5' 110.44(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O6 C5 C6 N1 -11.78(19) . . . . ?
O5 C5 C6 N1 169.13(12) . . . . ?
O3 C3 C4 O4 0.5(3) . . . . ?
C2 C3 C4 O4 179.31(19) . . . . ?
O3 C3 C4 C1 -178.46(18) . . . . ?
C2 C3 C4 C1 0.36(11) . . . . ?
O1 C1 C4 O4 1.3(3) . . . . ?
C2 C1 C4 O4 -179.30(19) . . . . ?
O1 C1 C4 C3 -179.73(16) . . . . ?
C2 C1 C4 C3 -0.35(11) . . . . ?
O3 C3 C2 O2 -1.4(3) . . . . ?
C4 C3 C2 O2 179.75(17) . . . . ?
O3 C3 C2 C1 178.52(17) . . . . ?
C4 C3 C2 C1 -0.36(11) . . . . ?
O1 C1 C2 O2 -0.4(3) . . . . ?
C4 C1 C2 O2 -179.76(18) . . . . ?
O1 C1 C2 C3 179.73(16) . . . . ?
C4 C1 C2 C3 0.36(11) . . . . ?
O6' C5' C6' N1' 9.21(19) . . . . ?
O5' C5' C6' N1' -170.44(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.935
_diffrn_reflns_theta_full        27.59
_diffrn_measured_fraction_theta_full 0.935
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 966748'
#######################################################################
#
#                 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_m
_audit_creation_method           SHELXL-97
_chemical_name_common            'Sarcosinium hydrogen squarate semihydrate'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C4 H O4), 2(C3 H8 N O2), H2 O'
_chemical_formula_sum            'C14 H20 N2 O13'
_chemical_formula_weight         424.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  -C2yc

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

_cell_length_a                   16.6068(2)
_cell_length_b                   7.21436(8)
_cell_length_c                   15.44410(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.0249(11)
_cell_angle_gamma                90.00
_cell_volume                     1836.43(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      5.37
_cell_measurement_theta_max      75.31

__exptl_crystal_description      plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    1.213
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_T_max  0.824
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (1990)).
;
_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6657
_diffrn_reflns_av_R_equivalents  0.0098
_diffrn_reflns_av_sigmaI/netI    0.0075
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.37
_diffrn_reflns_theta_max         75.31
_reflns_number_total             1862
_reflns_number_gt                1823
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury (2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0842P)²+1.1792P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1862
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.1020
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   0.807
_refine_ls_restrained_S_all      0.807
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18510(5) 0.32440(14) 1.09384(5) 0.0471(3) Uani 1 1 d . . .
O2 O -0.01061(5) 0.33835(15) 1.08733(6) 0.0511(3) Uani 1 1 d . . .
O3 O -0.02669(5) 0.13661(14) 0.89640(5) 0.0445(2) Uani 1 1 d . . .
O4 O 0.16270(5) 0.14030(13) 0.89790(5) 0.0424(2) Uani 1 1 d . . .
H4 H 0.2196(11) 0.161(2) 0.9133(10) 0.051 Uiso 1 1 d . . .
C1 C 0.12647(6) 0.27889(16) 1.03936(7) 0.0336(2) Uani 1 1 d . . .
C2 C 0.03628(7) 0.28411(16) 1.03831(7) 0.0353(3) Uani 1 1 d . . .
C3 C 0.02975(6) 0.19377(15) 0.95053(7) 0.0330(3) Uani 1 1 d . . .
C4 C 0.11596(6) 0.19706(15) 0.95487(7) 0.0317(2) Uani 1 1 d . . .
O5 O -0.17868(6) 0.17922(16) 0.92005(6) 0.0535(3) Uani 1 1 d . . .
H3 H -0.1261(12) 0.152(3) 0.9126(12) 0.064 Uiso 1 1 d . . .
C5 C -0.22616(7) 0.13708(16) 0.84835(7) 0.0370(3) Uani 1 1 d . . .
O6 O -0.20558(5) 0.05538(15) 0.78697(6) 0.0511(3) Uani 1 1 d . . .
C6 C -0.31098(7) 0.20913(19) 0.85111(8) 0.0440(3) Uani 1 1 d . . .
H61 H -0.3337 0.1529 0.8998 0.053 Uiso 1 1 calc R . .
H62 H -0.3091 0.3421 0.8603 0.053 Uiso 1 1 calc R . .
N1 N -0.36369(6) 0.16776(15) 0.76942(6) 0.0391(3) Uani 1 1 d . . .
H1N H -0.4117(9) 0.246(2) 0.7662(9) 0.047 Uiso 1 1 d . . .
H2N H -0.3352(9) 0.195(2) 0.7242(10) 0.047 Uiso 1 1 d . . .
C7 C -0.39211(8) -0.0261(2) 0.76185(9) 0.0473(3) Uani 1 1 d . . .
H71 H -0.4235 -0.0442 0.7061 0.057 Uiso 1 1 calc R . .
H72 H -0.4251 -0.0521 0.8073 0.057 Uiso 1 1 calc R . .
H73 H -0.3462 -0.1080 0.7673 0.057 Uiso 1 1 calc R . .
O1W O 0.0000 -0.08533(16) 0.7500 0.0367(3) Uani 1 2 d S . .
H1W H 0.0041(9) -0.014(2) 0.7069(9) 0.044 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 C1 1.2504(14) . ?
O2 C2 1.2153(14) . ?
O3 C3 1.2473(14) . ?
O4 C4 1.3082(13) . ?
C1 C4 1.4234(14) . ?
C1 C2 1.4963(14) . ?
C2 C3 1.4962(15) . ?
C3 C4 1.4252(14) . ?
O5 C5 1.3142(15) . ?
C5 O6 1.2009(14) . ?
C5 C6 1.5069(15) . ?
C6 N1 1.4755(16) . ?
N1 C7 1.4758(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
O1 C1 C4 136.38(10) . . ?
O1 C1 C2 134.17(10) . . ?
C4 C1 C2 89.44(8) . . ?
O2 C2 C3 136.37(11) . . ?
O2 C2 C1 135.90(11) . . ?
C3 C2 C1 87.73(8) . . ?
O3 C3 C4 134.85(10) . . ?
O3 C3 C2 135.76(10) . . ?
C4 C3 C2 89.37(8) . . ?
O4 C4 C3 129.67(10) . . ?
O4 C4 C1 136.89(10) . . ?
C3 C4 C1 93.43(9) . . ?
O6 C5 O5 125.40(11) . . ?
O6 C5 C6 123.30(11) . . ?
O5 C5 C6 111.28(10) . . ?
N1 C6 C5 111.40(10) . . ?
C7 N1 C6 114.20(10) . . ?

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 C1 C2 O2 2.9(2) . . . . ?
C4 C1 C2 O2 -178.62(15) . . . . ?
O1 C1 C2 C3 -177.21(14) . . . . ?
C4 C1 C2 C3 1.26(8) . . . . ?
O2 C2 C3 O3 -2.3(3) . . . . ?
C1 C2 C3 O3 177.80(14) . . . . ?
O2 C2 C3 C4 178.62(15) . . . . ?
C1 C2 C3 C4 -1.26(8) . . . . ?
O3 C3 C4 O4 1.9(2) . . . . ?
C2 C3 C4 O4 -179.06(12) . . . . ?
O3 C3 C4 C1 -177.75(14) . . . . ?
C2 C3 C4 C1 1.33(9) . . . . ?
O1 C1 C4 O4 -2.5(3) . . . . ?
C2 C1 C4 O4 179.10(14) . . . . ?
O1 C1 C4 C3 177.08(15) . . . . ?
C2 C1 C4 C3 -1.33(9) . . . . ?
O6 C5 C6 N1 -0.54(18) . . . . ?
O5 C5 C6 N1 178.00(10) . . . . ?
C5 C6 N1 C7 77.24(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        75.31
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 966749'
#######################################################################
#
#                 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_m
_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Dimethylglycine-squaric acid'
_chemical_name_common            'Dimethylglycinium hydrogen squarate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H2 O4, C4 H O4, C4 H9 N O2, C4 H10 N O2'
_chemical_formula_sum            'C16 H22 N2 O12'
_chemical_formula_weight         434.36

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc

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

_cell_length_a                   17.5110(5)
_cell_length_b                   6.5385(2)
_cell_length_c                   17.3475(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.249(3)
_cell_angle_gamma                90.00
_cell_volume                     1886.32(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      29.13

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      1.529
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (1990)).
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11666
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         29.13
_reflns_number_total             4520
_reflns_number_gt                3180
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury (2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0609P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4520
_refine_ls_number_parameters     341
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.008

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2' O 0.35087(6) 0.48035(17) -0.00261(6) 0.0255(3) Uani 1 1 d . . .
O4' O 0.21030(6) 0.59182(17) 0.17676(7) 0.0228(2) Uani 1 1 d . . .
H4' H 0.2429(10) 0.600(3) 0.2315(11) 0.027 Uiso 1 1 d . . .
C3' C 0.22892(8) 0.5167(2) 0.04320(9) 0.0180(3) Uani 1 1 d . . .
O3' O 0.16267(6) 0.49814(16) -0.01198(6) 0.0241(3) Uani 1 1 d . . .
C4' C 0.25328(8) 0.5584(2) 0.12777(9) 0.0168(3) Uani 1 1 d . . .
C1' C 0.33811(9) 0.5486(2) 0.13719(9) 0.0176(3) Uani 1 1 d . . .
C2' C 0.31498(9) 0.5071(2) 0.04676(9) 0.0180(3) Uani 1 1 d . . .
O1' O 0.40137(6) 0.56439(16) 0.19402(6) 0.0226(2) Uani 1 1 d . . .
H3' H 0.1668(10) 0.431(2) -0.0984(11) 0.027 Uiso 1 1 d . . .
O6' O 0.03993(6) 0.46100(16) -0.19874(6) 0.0236(3) Uani 1 1 d . . .
O5' O 0.17057(6) 0.37891(17) -0.14707(7) 0.0246(3) Uani 1 1 d . . .
N1' N 0.03346(7) 0.33949(19) -0.35094(7) 0.0192(3) Uani 1 1 d . . .
H1' H -0.0118(10) 0.326(2) -0.3352(9) 0.023 Uiso 1 1 d . . .
C5' C 0.10153(8) 0.3874(2) -0.20447(9) 0.0181(3) Uani 1 1 d . . .
C6' C 0.10488(9) 0.2865(2) -0.28141(9) 0.0189(3) Uani 1 1 d . . .
H61' H 0.1521(10) 0.325(2) -0.2928(9) 0.023 Uiso 1 1 d . . .
H62' H 0.1049(9) 0.140(3) -0.2728(9) 0.023 Uiso 1 1 d . . .
C7' C 0.03446(11) 0.5572(3) -0.37548(11) 0.0284(4) Uani 1 1 d . . .
H71' H 0.0409(10) 0.645(3) -0.3260(11) 0.034 Uiso 1 1 d . . .
H72' H -0.0166(11) 0.586(3) -0.4189(11) 0.034 Uiso 1 1 d . . .
H73' H 0.0786(11) 0.571(3) -0.4003(10) 0.034 Uiso 1 1 d . . .
C8' C 0.02550(11) 0.1995(3) -0.42148(10) 0.0268(4) Uani 1 1 d . . .
H81' H 0.0251(10) 0.060(3) -0.4029(10) 0.032 Uiso 1 1 d . . .
H82' H 0.0719(10) 0.225(2) -0.4431(10) 0.032 Uiso 1 1 d . . .
H83' H -0.0263(10) 0.229(2) -0.4649(10) 0.032 Uiso 1 1 d . . .
O2 O 0.12024(6) 0.61637(16) 0.33534(6) 0.0228(2) Uani 1 1 d . . .
O4 O 0.36926(6) 0.50534(16) 0.51876(7) 0.0215(2) Uani 1 1 d . . .
H4 H 0.3708(10) 0.485(2) 0.5691(11) 0.026 Uiso 1 1 d . . .
O1 O 0.30242(6) 0.59794(17) 0.32865(6) 0.0239(3) Uani 1 1 d . . .
O3 O 0.18337(7) 0.50554(17) 0.52633(7) 0.0229(3) Uani 1 1 d . . .
H3 H 0.2176 0.4863 0.5704 0.028 Uiso 1 1 calc G . .
C4 C 0.29752(8) 0.5337(2) 0.46830(9) 0.0175(3) Uani 1 1 d . . .
C3 C 0.21784(8) 0.5352(2) 0.47177(9) 0.0172(3) Uani 1 1 d . . .
C2 C 0.18566(8) 0.5841(2) 0.38506(8) 0.0176(3) Uani 1 1 d . . .
C1 C 0.27040(8) 0.5777(2) 0.38236(9) 0.0181(3) Uani 1 1 d . . .
O6 O 0.39124(6) 0.45319(16) 0.66849(6) 0.0231(2) Uani 1 1 d . . .
O5 O 0.26282(6) 0.43843(16) 0.66727(6) 0.0259(3) Uani 1 1 d . . .
N1 N 0.44670(7) 0.40763(19) 0.83575(7) 0.0188(3) Uani 1 1 d . . .
H1 H 0.4754(9) 0.389(2) 0.8017(10) 0.023 Uiso 1 1 d . . .
C5 C 0.33804(9) 0.4262(2) 0.70113(9) 0.0190(3) Uani 1 1 d . . .
C6 C 0.36176(9) 0.3605(3) 0.78892(9) 0.0222(3) Uani 1 1 d . . .
H61 H 0.3548(9) 0.210(3) 0.7884(10) 0.027 Uiso 1 1 d . . .
H62 H 0.3300(10) 0.422(2) 0.8183(10) 0.027 Uiso 1 1 d . . .
C7 C 0.45659(10) 0.6261(2) 0.86231(10) 0.0235(3) Uani 1 1 d . . .
H71 H 0.4371(10) 0.713(3) 0.8127(10) 0.028 Uiso 1 1 d . . .
H72 H 0.4253(10) 0.648(3) 0.8996(10) 0.028 Uiso 1 1 d . . .
H73 H 0.5117(11) 0.648(2) 0.8900(10) 0.028 Uiso 1 1 d . . .
C8 C 0.47576(10) 0.2657(3) 0.90612(10) 0.0257(4) Uani 1 1 d . . .
H81 H 0.4717(10) 0.129(3) 0.8850(10) 0.031 Uiso 1 1 d . . .
H82 H 0.5301(10) 0.304(3) 0.9387(10) 0.031 Uiso 1 1 d . . .
H83 H 0.4408(10) 0.281(3) 0.9384(10) 0.031 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
O2' C2' 1.2231(17) . ?
O4' C4' 1.3179(17) . ?
C3' O3' 1.2576(17) . ?
C3' C4' 1.420(2) . ?
C3' C2' 1.490(2) . ?
C4' C1' 1.444(2) . ?
C1' O1' 1.2352(17) . ?
C1' C2' 1.517(2) . ?
O6' C5' 1.2133(16) . ?
O5' C5' 1.3046(17) . ?
N1' C6' 1.4812(18) . ?
N1' C7' 1.488(2) . ?
N1' C8' 1.499(2) . ?
C5' C6' 1.506(2) . ?
O2 C2 1.2175(16) . ?
O4 C4 1.3001(17) . ?
O1 C1 1.2358(17) . ?
O3 C3 1.2866(17) . ?
C4 C3 1.4152(19) . ?
C4 C1 1.445(2) . ?
C3 C2 1.467(2) . ?
C2 C1 1.4998(19) . ?
O6 C5 1.2449(17) . ?
O5 C5 1.2657(18) . ?
N1 C6 1.4867(19) . ?
N1 C8 1.4905(19) . ?
N1 C7 1.494(2) . ?
C5 C6 1.510(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
O3' C3' C4' 135.39(13) . . ?
O3' C3' C2' 135.02(13) . . ?
C4' C3' C2' 89.58(11) . . ?
O4' C4' C3' 130.59(13) . . ?
O4' C4' C1' 135.17(13) . . ?
C3' C4' C1' 94.24(11) . . ?
O1' C1' C4' 136.09(13) . . ?
O1' C1' C2' 136.27(13) . . ?
C4' C1' C2' 87.64(11) . . ?
O2' C2' C3' 135.38(14) . . ?
O2' C2' C1' 136.08(14) . . ?
C3' C2' C1' 88.53(11) . . ?
C6' N1' C7' 111.98(13) . . ?
C6' N1' C8' 111.15(12) . . ?
C7' N1' C8' 110.92(13) . . ?
O6' C5' O5' 126.12(14) . . ?
O6' C5' C6' 121.91(13) . . ?
O5' C5' C6' 111.94(12) . . ?
N1' C6' C5' 111.22(12) . . ?
O4 C4 C3 136.90(14) . . ?
O4 C4 C1 131.23(13) . . ?
C3 C4 C1 91.87(12) . . ?
O3 C3 C4 136.56(14) . . ?
O3 C3 C2 132.00(13) . . ?
C4 C3 C2 91.44(11) . . ?
O2 C2 C3 137.60(13) . . ?
O2 C2 C1 134.70(13) . . ?
C3 C2 C1 87.70(11) . . ?
O1 C1 C4 135.99(13) . . ?
O1 C1 C2 135.03(13) . . ?
C4 C1 C2 88.97(11) . . ?
C6 N1 C8 110.18(12) . . ?
C6 N1 C7 111.48(12) . . ?
C8 N1 C7 111.46(12) . . ?
O6 C5 O5 126.73(14) . . ?
O6 C5 C6 119.37(13) . . ?
O5 C5 C6 113.81(13) . . ?
N1 C6 C5 113.84(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3' C3' C4' O4' 0.2(3) . . . . ?
C2' C3' C4' O4' 179.40(15) . . . . ?
O3' C3' C4' C1' 179.91(17) . . . . ?
C2' C3' C4' C1' -0.87(11) . . . . ?
O4' C4' C1' O1' 1.4(3) . . . . ?
C3' C4' C1' O1' -178.27(17) . . . . ?
O4' C4' C1' C2' -179.44(16) . . . . ?
C3' C4' C1' C2' 0.86(11) . . . . ?
O3' C3' C2' O2' 1.1(3) . . . . ?
C4' C3' C2' O2' -178.16(17) . . . . ?
O3' C3' C2' C1' -179.95(17) . . . . ?
C4' C3' C2' C1' 0.83(11) . . . . ?
O1' C1' C2' O2' -2.7(3) . . . . ?
C4' C1' C2' O2' 178.16(18) . . . . ?
O1' C1' C2' C3' 178.31(17) . . . . ?
C4' C1' C2' C3' -0.82(11) . . . . ?
C7' N1' C6' C5' 70.14(15) . . . . ?
C8' N1' C6' C5' -165.18(12) . . . . ?
O6' C5' C6' N1' 15.4(2) . . . . ?
O5' C5' C6' N1' -166.41(12) . . . . ?
O4 C4 C3 O3 -1.5(3) . . . . ?
C1 C4 C3 O3 178.43(17) . . . . ?
O4 C4 C3 C2 179.03(17) . . . . ?
C1 C4 C3 C2 -1.07(11) . . . . ?
O3 C3 C2 O2 1.5(3) . . . . ?
C4 C3 C2 O2 -178.98(18) . . . . ?
O3 C3 C2 C1 -178.51(16) . . . . ?
C4 C3 C2 C1 1.03(11) . . . . ?
O4 C4 C1 O1 2.2(3) . . . . ?
C3 C4 C1 O1 -177.74(17) . . . . ?
O4 C4 C1 C2 -179.04(15) . . . . ?
C3 C4 C1 C2 1.04(11) . . . . ?
O2 C2 C1 O1 -2.2(3) . . . . ?
C3 C2 C1 O1 177.79(17) . . . . ?
O2 C2 C1 C4 179.01(17) . . . . ?
C3 C2 C1 C4 -1.01(11) . . . . ?
C8 N1 C6 C5 -155.18(13) . . . . ?
C7 N1 C6 C5 80.51(16) . . . . ?
O6 C5 C6 N1 21.4(2) . . . . ?
O5 C5 C6 N1 -161.82(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.893
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.893
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 966750'
#######################################################################
#
#                 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_m
_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Betainium hydrogen squarate'
_chemical_name_common            'Betainium hydrogen squarate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H1 O4, C5 H12 N1 O2'
_chemical_formula_sum            'C9 H13 N1 O6'
_chemical_formula_weight         231.20

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

_symmetry_cell_setting           Orthorhombic

_symmetry_space_group_name_H-M   Pca2(1)
_symmetry_space_group_name_Hall  P2c-2ac

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

_cell_length_a                   22.2718(14)
_cell_length_b                   6.0451(3)
_cell_length_c                   16.2765(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2191.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      29.14

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      1.402
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   
;  
Correction for absorption was made using XEMP (SHELXTL,
Sheldrick (1990)). 
;
_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8662
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0724
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         29.14
_reflns_number_total             4068
_reflns_number_gt                2147
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury (2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0639P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.4(15)
_refine_ls_number_reflns         4068
_refine_ls_number_parameters     297
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   0.766
_refine_ls_restrained_S_all      0.766
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.31888(11) -0.1765(4) 0.51500(15) 0.0531(7) Uani 1 1 d . . .
O3 O 0.36626(15) 0.0060(4) 0.3353(2) 0.0536(9) Uani 1 1 d . . .
H3 H 0.3912(18) -0.121(7) 0.349(2) 0.064 Uiso 1 1 d . . .
O1 O 0.22901(12) 0.2366(4) 0.52535(18) 0.0640(8) Uani 1 1 d . . .
C3 C 0.32767(16) 0.0692(6) 0.3917(2) 0.0367(8) Uani 1 1 d . . .
C2 C 0.30825(18) -0.0160(5) 0.4690(3) 0.0375(11) Uani 1 1 d . . .
C1 C 0.26595(16) 0.1749(5) 0.4761(2) 0.0397(8) Uani 1 1 d . . .
C4 C 0.28836(16) 0.2523(5) 0.3954(2) 0.0399(8) Uani 1 1 d . . .
O4 O 0.27655(12) 0.4094(4) 0.34916(16) 0.0630(8) Uani 1 1 d . . .
O2' O 0.43765(11) -0.3107(4) 0.35189(14) 0.0544(7) Uani 1 1 d . . .
O3' O 0.38509(14) -0.5093(4) 0.5260(2) 0.0519(8) Uani 1 1 d . . .
H3' H 0.3661(17) -0.379(6) 0.518(2) 0.062 Uiso 1 1 d . . .
O1' O 0.53019(13) -0.7210(4) 0.34478(17) 0.0713(8) Uani 1 1 d . . .
O4' O 0.47238(11) -0.9180(4) 0.51184(15) 0.0577(7) Uani 1 1 d . . .
C2' C 0.44702(18) -0.4756(6) 0.3954(3) 0.0368(10) Uani 1 1 d . . .
C4' C 0.46342(15) -0.7528(5) 0.4673(2) 0.0407(8) Uani 1 1 d . . .
C1' C 0.48960(17) -0.6649(5) 0.3902(2) 0.0434(9) Uani 1 1 d . . .
C3' C 0.42476(15) -0.5641(6) 0.4707(2) 0.0361(8) Uani 1 1 d . . .
O5 O 0.19878(12) 0.7136(4) 0.37422(15) 0.0536(7) Uani 1 1 d . . .
H4 H 0.2183 0.6007 0.3661 0.064 Uiso 1 1 calc R . .
N1 N 0.12619(11) 1.1090(4) 0.23774(17) 0.0370(7) Uani 1 1 d . . .
C6 C 0.14749(19) 1.0039(5) 0.3148(2) 0.0336(10) Uani 1 1 d . . .
H61 H 0.1128 0.9477 0.3442 0.040 Uiso 1 1 calc R . .
H62 H 0.1656 1.1175 0.3488 0.040 Uiso 1 1 calc R . .
C5 C 0.19170(16) 0.8190(5) 0.3054(2) 0.0426(9) Uani 1 1 d . . .
C8 C 0.0943(2) 0.9426(7) 0.1839(3) 0.0640(12) Uani 1 1 d . . .
H81 H 0.1221 0.8299 0.1672 0.077 Uiso 1 1 calc R . .
H82 H 0.0786 1.0159 0.1362 0.077 Uiso 1 1 calc R . .
H83 H 0.0619 0.8764 0.2141 0.077 Uiso 1 1 calc R . .
O6 O 0.21717(15) 0.7707(5) 0.24249(18) 0.0860(10) Uani 1 1 d . . .
C9 C 0.08213(18) 1.2863(6) 0.2617(3) 0.0695(12) Uani 1 1 d . . .
H91 H 0.1021 1.3957 0.2946 0.083 Uiso 1 1 calc R . .
H92 H 0.0499 1.2216 0.2927 0.083 Uiso 1 1 calc R . .
H93 H 0.0662 1.3547 0.2131 0.083 Uiso 1 1 calc R . .
C7 C 0.17649(17) 1.2146(6) 0.1909(2) 0.0564(10) Uani 1 1 d . . .
H71 H 0.2045 1.1029 0.1739 0.068 Uiso 1 1 calc R . .
H72 H 0.1966 1.3200 0.2254 0.068 Uiso 1 1 calc R . .
H73 H 0.1607 1.2885 0.1434 0.068 Uiso 1 1 calc R . .
N1' N 0.62759(13) -1.6220(4) 0.61755(16) 0.0399(7) Uani 1 1 d . . .
O5' O 0.55356(12) -1.2081(4) 0.48909(16) 0.0537(6) Uani 1 1 d . . .
H4' H 0.5268 -1.1169 0.4958 0.064 Uiso 1 1 calc R . .
C6' C 0.6074(2) -1.5018(5) 0.5409(3) 0.0418(11) Uani 1 1 d . . .
H61' H 0.5929 -1.6100 0.5016 0.050 Uiso 1 1 calc R . .
H62' H 0.6420 -1.4290 0.5167 0.050 Uiso 1 1 calc R . .
C5' C 0.55856(16) -1.3305(6) 0.5548(2) 0.0410(9) Uani 1 1 d . . .
O6' O 0.52896(13) -1.3122(5) 0.61486(18) 0.0744(9) Uani 1 1 d . . .
C9' C 0.57770(19) -1.7588(6) 0.6538(2) 0.0576(10) Uani 1 1 d . . .
H91' H 0.5632 -1.8611 0.6133 0.069 Uiso 1 1 calc R . .
H92' H 0.5456 -1.6634 0.6708 0.069 Uiso 1 1 calc R . .
H93' H 0.5926 -1.8392 0.7004 0.069 Uiso 1 1 calc R . .
C7' C 0.67798(19) -1.7699(7) 0.5911(3) 0.0705(12) Uani 1 1 d . . .
H71' H 0.6637 -1.8722 0.5505 0.085 Uiso 1 1 calc R . .
H72' H 0.6928 -1.8502 0.6378 0.085 Uiso 1 1 calc R . .
H73' H 0.7097 -1.6820 0.5682 0.085 Uiso 1 1 calc R . .
C8' C 0.6506(2) -1.4651(6) 0.6806(3) 0.0589(12) Uani 1 1 d . . .
H81' H 0.6632 -1.5461 0.7284 0.071 Uiso 1 1 calc R . .
H82' H 0.6194 -1.3632 0.6956 0.071 Uiso 1 1 calc R . .
H83' H 0.6842 -1.3848 0.6587 0.071 Uiso 1 1 calc R . .


_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
O2 C2 1.248(4) . ?
O3 C3 1.314(4) . ?
O3 H3 0.97(4) . ?
O1 C1 1.207(4) . ?
C3 C4 1.413(5) . ?
C3 C2 1.427(5) . ?
C2 C1 1.494(5) . ?
C1 C4 1.482(5) . ?
C4 O4 1.240(4) . ?
O2' C2' 1.240(4) . ?
O3' C3' 1.304(4) . ?
O3' H3' 0.90(4) . ?
O1' C1' 1.216(4) . ?
O4' C4' 1.250(4) . ?
C2' C3' 1.427(5) . ?
C2' C1' 1.488(5) . ?
C4' C3' 1.430(5) . ?
C4' C1' 1.481(5) . ?
O5 C5 1.298(4) . ?
O5 H4 0.8200 . ?
N1 C6 1.484(5) . ?
N1 C7 1.498(4) . ?
N1 C9 1.505(4) . ?
N1 C8 1.511(5) . ?
C6 C5 1.498(5) . ?
C6 H61 0.9700 . ?
C6 H62 0.9700 . ?
C5 O6 1.207(4) . ?
C8 H81 0.9600 . ?
C8 H82 0.9600 . ?
C8 H83 0.9600 . ?
C9 H91 0.9600 . ?
C9 H92 0.9600 . ?
C9 H93 0.9600 . ?
C7 H71 0.9600 . ?
C7 H72 0.9600 . ?
C7 H73 0.9600 . ?
N1' C8' 1.489(4) . ?
N1' C7' 1.498(5) . ?
N1' C9' 1.506(4) . ?
N1' C6' 1.512(5) . ?
O5' C5' 1.305(4) . ?
O5' H4' 0.8200 . ?
C6' C5' 1.520(5) . ?
C6' H61' 0.9700 . ?
C6' H62' 0.9700 . ?
C5' O6' 1.185(4) . ?
C9' H91' 0.9600 . ?
C9' H92' 0.9600 . ?
C9' H93' 0.9600 . ?
C7' H71' 0.9600 . ?
C7' H72' 0.9600 . ?
C7' H73' 0.9600 . ?
C8' H81' 0.9600 . ?
C8' H82' 0.9600 . ?
C8' H83' 0.9600 . ?

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 O3 H3 116(2) . . ?
O3 C3 C4 131.5(3) . . ?
O3 C3 C2 135.2(3) . . ?
C4 C3 C2 93.3(3) . . ?
O2 C2 C3 138.7(4) . . ?
O2 C2 C1 132.4(4) . . ?
C3 C2 C1 88.9(3) . . ?
O1 C1 C4 136.1(3) . . ?
O1 C1 C2 136.0(3) . . ?
C4 C1 C2 87.9(3) . . ?
O4 C4 C3 134.9(3) . . ?
O4 C4 C1 135.1(3) . . ?
C3 C4 C1 89.9(3) . . ?
C3' O3' H3' 116(3) . . ?
O2' C2' C3' 137.2(3) . . ?
O2' C2' C1' 133.9(4) . . ?
C3' C2' C1' 88.9(3) . . ?
O4' C4' C3' 135.2(3) . . ?
O4' C4' C1' 135.6(3) . . ?
C3' C4' C1' 89.1(3) . . ?
O1' C1' C4' 135.0(3) . . ?
O1' C1' C2' 136.2(4) . . ?
C4' C1' C2' 88.7(3) . . ?
O3' C3' C2' 137.1(3) . . ?
O3' C3' C4' 129.6(3) . . ?
C2' C3' C4' 93.2(3) . . ?
C5 O5 H4 109.5 . . ?
C6 N1 C7 111.9(3) . . ?
C6 N1 C9 107.1(3) . . ?
C7 N1 C9 108.5(3) . . ?
C6 N1 C8 110.8(3) . . ?
C7 N1 C8 109.9(3) . . ?
C9 N1 C8 108.5(3) . . ?
N1 C6 C5 116.3(3) . . ?
N1 C6 H61 108.2 . . ?
C5 C6 H61 108.2 . . ?
N1 C6 H62 108.2 . . ?
C5 C6 H62 108.2 . . ?
H61 C6 H62 107.4 . . ?
O6 C5 O5 123.8(3) . . ?
O6 C5 C6 125.2(3) . . ?
O5 C5 C6 111.0(3) . . ?
N1 C8 H81 109.5 . . ?
N1 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
N1 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
N1 C9 H91 109.5 . . ?
N1 C9 H92 109.5 . . ?
H91 C9 H92 109.5 . . ?
N1 C9 H93 109.5 . . ?
H91 C9 H93 109.5 . . ?
H92 C9 H93 109.5 . . ?
N1 C7 H71 109.5 . . ?
N1 C7 H72 109.5 . . ?
H71 C7 H72 109.5 . . ?
N1 C7 H73 109.5 . . ?
H71 C7 H73 109.5 . . ?
H72 C7 H73 109.5 . . ?
C8' N1' C7' 108.6(3) . . ?
C8' N1' C9' 109.5(3) . . ?
C7' N1' C9' 109.7(3) . . ?
C8' N1' C6' 111.4(3) . . ?
C7' N1' C6' 105.8(3) . . ?
C9' N1' C6' 111.6(3) . . ?
C5' O5' H4' 109.5 . . ?
N1' C6' C5' 114.7(3) . . ?
N1' C6' H61' 108.6 . . ?
C5' C6' H61' 108.6 . . ?
N1' C6' H62' 108.6 . . ?
C5' C6' H62' 108.6 . . ?
H61' C6' H62' 107.6 . . ?
O6' C5' O5' 125.2(3) . . ?
O6' C5' C6' 125.8(4) . . ?
O5' C5' C6' 109.0(3) . . ?
N1' C9' H91' 109.5 . . ?
N1' C9' H92' 109.5 . . ?
H91' C9' H92' 109.5 . . ?
N1' C9' H93' 109.5 . . ?
H91' C9' H93' 109.5 . . ?
H92' C9' H93' 109.5 . . ?
N1' C7' H71' 109.5 . . ?
N1' C7' H72' 109.5 . . ?
H71' C7' H72' 109.5 . . ?
N1' C7' H73' 109.5 . . ?
H71' C7' H73' 109.5 . . ?
H72' C7' H73' 109.5 . . ?
N1' C8' H81' 109.5 . . ?
N1' C8' H82' 109.5 . . ?
H81' C8' H82' 109.5 . . ?
N1' C8' H83' 109.5 . . ?
H81' C8' H83' 109.5 . . ?
H82' C8' H83' 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 C3 C2 O2 0.8(8) . . . . ?
C4 C3 C2 O2 179.6(5) . . . . ?
O3 C3 C2 C1 -178.9(4) . . . . ?
C4 C3 C2 C1 -0.1(3) . . . . ?
O2 C2 C1 O1 -0.8(7) . . . . ?
C3 C2 C1 O1 179.0(4) . . . . ?
O2 C2 C1 C4 -179.6(4) . . . . ?
C3 C2 C1 C4 0.1(3) . . . . ?
O3 C3 C4 O4 0.5(7) . . . . ?
C2 C3 C4 O4 -178.3(4) . . . . ?
O3 C3 C4 C1 179.0(4) . . . . ?
C2 C3 C4 C1 0.1(3) . . . . ?
O1 C1 C4 O4 -0.5(7) . . . . ?
C2 C1 C4 O4 178.3(4) . . . . ?
O1 C1 C4 C3 -179.0(4) . . . . ?
C2 C1 C4 C3 -0.1(3) . . . . ?
O4' C4' C1' O1' -2.3(7) . . . . ?
C3' C4' C1' O1' 175.8(4) . . . . ?
O4' C4' C1' C2' -179.8(4) . . . . ?
C3' C4' C1' C2' -1.7(3) . . . . ?
O2' C2' C1' O1' 2.6(8) . . . . ?
C3' C2' C1' O1' -175.7(5) . . . . ?
O2' C2' C1' C4' -180.0(5) . . . . ?
C3' C2' C1' C4' 1.7(3) . . . . ?
O2' C2' C3' O3' 0.0(9) . . . . ?
C1' C2' C3' O3' 178.2(4) . . . . ?
O2' C2' C3' C4' 180.0(5) . . . . ?
C1' C2' C3' C4' -1.8(3) . . . . ?
O4' C4' C3' O3' -0.1(7) . . . . ?
C1' C4' C3' O3' -178.2(4) . . . . ?
O4' C4' C3' C2' 179.9(4) . . . . ?
C1' C4' C3' C2' 1.8(3) . . . . ?
C7 N1 C6 C5 -61.9(4) . . . . ?
C9 N1 C6 C5 179.3(3) . . . . ?
C8 N1 C6 C5 61.1(4) . . . . ?
N1 C6 C5 O6 10.9(6) . . . . ?
N1 C6 C5 O5 -168.3(3) . . . . ?
C8' N1' C6' C5' -58.5(5) . . . . ?
C7' N1' C6' C5' -176.4(3) . . . . ?
C9' N1' C6' C5' 64.3(4) . . . . ?
N1' C6' C5' O6' -13.9(6) . . . . ?
N1' C6' C5' O5' 167.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.887
_diffrn_reflns_theta_full        29.14
_diffrn_measured_fraction_theta_full 0.887
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_database_code_depnum_ccdc_archive 'CCDC 966751'
