# 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

data_m 
_audit_creation_method            SHELXL-97
_publ_contact_author_name     'Zofia Dega-Szarfan'
_publ_contact_author_address
;Faculty of Chemistry,
Adam Mickiewicz University,
Umultowska 89b, 61-614  Poznan
Poland
;
_publ_contact_author_fax     '+48(61)8291555'
_publ_contact_author_phone     '+48(61)8291216'
_publ_contact_author_email     degasz@amu.edu.pl
_publ_section_title
;
Cocrystals of glycine and its methyl derivatives with squaric acid 
;
loop_
    _publ_author_name
   'Aniola, Michalina'
   'Dega-Szafran, Zofia'
   'Katrusiak, Andrzej'
   'Szafran, Miroslaw'
loop_
    _publ_author_footnote
; Faculty of Chemistry,
Adam Mickiewicz University,
Umultowska 89b, 61-614  Poznan
Poland
;
_publ_author_address
;Faculty of Chemistry,
Adam Mickiewicz University,
Umultowska 89b, 61-614  Poznan
Poland
;
_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

