# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_tgsq-
_audit_block_doi                 10.5517/cc14bl35
_database_code_depnum_ccdc_archive 'CCDC 1052856'
#Added by publCIF



_audit_update_record             
;
2016-02-05 deposited with the CCDC.
2016-02-26 downloaded from the CCDC.
;
#Added by publCIF


_publcif_datablock.id            {657b96e8-b324-4d94-b17b-852116ce1f31}


_refine_ls_number_constraints    ?
#Added by publCIF




_cell_special_details            'F(000) = 1104'

#Added by publCIF




_diffrn_radiation_monochromator  graphite
_audit_creation_date             2015-01-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.12 svn.r3133 for OlexSys, GUI svn.r4992)
;
_chemical_name_common            'Bis-glycine squarate'
_chemical_name_systematic        
;
Bis-glycine squarate
;

_chemical_formula_moiety         '2(C2 H5 N O2), 1(C4 H2 O4)'
_chemical_formula_sum            'C8 H12 N2 O8'
_chemical_formula_weight         264.20
_chemical_melting_point          ?
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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                   16.8050(16)
_cell_length_b                   8.3008(8)
_cell_length_c                   15.7976(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.259(9)
_cell_angle_gamma                90
_cell_volume                     2168.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2994
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3750
_cell_measurement_theta_min      3.6230
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40281
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrysAlisProAgilentTechnologies
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7068
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.483
_diffrn_reflns_theta_min         3.642
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9853
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2278
_reflns_number_total             2571
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       CrysAlisPro,Agilent-Technologies
_computing_data_collection       CrysAlisPro,Agilent-Technologies
_computing_data_reduction        CrysAlisPro,Agilent-Technologies
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    Olex2
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.681
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.027(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2571
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0589
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0941P)²+4.3161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1709
_refine_ls_wR_factor_ref         0.1759
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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

C8 C 0.12637(13) 1.1070(3) 0.22739(13) 0.0265(5) Uani 1 1 d . . . . .
H8A H 0.0998 1.1798 0.2616 0.032 Uiso 1 1 calc R . . . .
H8B H 0.0886 1.0218 0.2059 0.032 Uiso 1 1 calc R . . . .
08 O 0.22041(10) 1.2263(2) 0.15006(11) 0.0362(4) Uani 1 1 d . . . . .
N2 N 0.14138(13) 0.6430(3) 0.44481(12) 0.0355(5) Uani 1 1 d . . . . .
H2A H 0.1429 0.7453 0.4364 0.043 Uiso 1 1 calc R . . . .
H2B H 0.1533 0.6050 0.4961 0.043 Uiso 1 1 calc R . . . .
C7 C 0.11838(14) 0.5334(3) 0.37159(13) 0.0289(5) Uani 1 1 d . . . . .
H7A H 0.0710 0.4720 0.3791 0.035 Uiso 1 1 calc R . . . .
H7B H 0.1621 0.4583 0.3691 0.035 Uiso 1 1 calc R . . . .
O7 O 0.09515(11) 0.7707(2) 0.28710(12) 0.0385(4) Uani 1 1 d . . . . .
H5 H 0.1029 0.8062 0.3363 0.058 Uiso 1 1 calc R . . . .
O5 O 0.09169(13) 0.5327(2) 0.22184(11) 0.0429(5) Uani 1 1 d . . . . .
N1 N 0.19869(11) 1.0373(2) 0.28126(11) 0.0266(4) Uani 1 1 d . . . . .
H1A H 0.2455 1.0516 0.2677 0.032 Uiso 1 1 calc R . . . .
H1B H 0.1941 0.9823 0.3263 0.032 Uiso 1 1 calc R . . . .
O4 O 0.22494(9) 0.81570(19) 0.14547(9) 0.0289(4) Uani 1 1 d . . . . .
H4 H 0.2077 0.7540 0.1785 0.043 Uiso 1 1 calc R . . . .
O3 O 0.21405(10) 1.0121(2) -0.03524(10) 0.0345(4) Uani 1 1 d . . . . .
O6 O 0.09129(10) 1.2419(2) 0.09353(10) 0.0358(4) Uani 1 1 d . . . . .
H6 H 0.0482 1.2132 0.1063 0.054 Uiso 1 1 calc R . . . .
O2 O 0.04303(10) 0.8593(2) -0.10389(10) 0.0400(5) Uani 1 1 d . . . . .
C6 C 0.15003(12) 1.1974(2) 0.15284(12) 0.0236(4) Uani 1 1 d . . . . .
O1 O 0.04847(12) 0.6633(3) 0.07406(11) 0.0471(5) Uani 1 1 d . . . . .
H3 H 0.0693 0.6335 0.1224 0.071 Uiso 1 1 calc R . . . .
C1 C 0.09194(13) 0.8466(3) -0.03394(13) 0.0256(4) Uani 1 1 d . . . . .
C3 C 0.17475(12) 0.8275(2) 0.07796(12) 0.0226(4) Uani 1 1 d . . . . .
C5 C 0.10038(12) 0.6274(3) 0.28923(13) 0.0267(5) Uani 1 1 d . . . . .
C2 C 0.09483(13) 0.7579(3) 0.04585(13) 0.0274(5) Uani 1 1 d . . . . .
C4 C 0.17068(12) 0.9164(3) -0.00336(12) 0.0238(4) Uani 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

C8 N1 1.472(3) . ?
C8 C6 1.508(3) . ?
08 C6 1.215(3) . ?
N2 C7 1.468(3) . ?
C7 C5 1.501(3) . ?
O7 C5 1.192(3) . ?
O5 C5 1.311(3) . ?
O4 C3 1.240(2) . ?
O3 C4 1.243(3) . ?
O6 C6 1.288(3) . ?
O2 C1 1.259(2) . ?
O1 C2 1.243(3) . ?
C1 C2 1.453(3) . ?
C1 C4 1.446(3) . ?
C3 C2 1.467(3) . ?
C3 C4 1.472(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

N1 C8 C6 109.97(17) . . ?
N2 C7 C5 110.16(18) . . ?
08 C6 C8 121.34(19) . . ?
08 C6 O6 122.79(19) . . ?
O6 C6 C8 115.87(18) . . ?
O2 C1 C2 136.0(2) . . ?
O2 C1 C4 132.49(19) . . ?
C4 C1 C2 91.48(16) . . ?
O4 C3 C2 134.97(19) . . ?
O4 C3 C4 135.13(19) . . ?
C2 C3 C4 89.90(16) . . ?
O7 C5 C7 123.1(2) . . ?
O7 C5 O5 125.4(2) . . ?
O5 C5 C7 111.59(19) . . ?
O1 C2 C1 134.8(2) . . ?
O1 C2 C3 135.92(19) . . ?
C1 C2 C3 89.28(16) . . ?
O3 C4 C1 133.45(18) . . ?
O3 C4 C3 137.21(19) . . ?
C1 C4 C3 89.34(16) . . ?



