#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/43/7054323.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7054323
loop_
_publ_author_name
'Anioła, Michalina'
'Dega-Szafran, Zofia'
'Katrusiak, Andrzej'
'Szafran, Mirosław'
_publ_section_title
;
 NH⋯O and OH⋯O interactions of glycine derivatives with
 squaric acid
;
_journal_issue                   8
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              3556
_journal_paper_doi               10.1039/C4NJ00212A
_journal_volume                  38
_journal_year                    2014
_chemical_formula_moiety         'C4 O4, 2(C2 H6 N O2)'
_chemical_formula_sum            'C8 H12 N2 O8'
_chemical_formula_weight         264.20
_chemical_melting_point          'Diglycinium squarate'
_chemical_name_common            'Diglycinium squarate'
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.063(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.8392(3)
_cell_length_b                   8.3163(2)
_cell_length_c                   15.8267(3)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.59
_cell_measurement_theta_min      3.13
_cell_volume                     2182.27(8)
_computing_cell_refinement       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlis (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'Mercury (2008)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0112
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10909
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.146
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
; 
Correction for absorption was made using XEMP (SHELXTL, 
Sheldrick (1990)).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_meas      1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.697
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2371
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.697
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1067P)²+3.7054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                2149
_reflns_number_total             2371
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7054215
_cod_data_source_file            c4nj00212a5.cif
_cod_data_source_block           m
_cod_original_sg_symbol_Hall     -C2yc
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7054323
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'
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
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
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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)
