#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/43/7054322.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_7054322
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 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
_chemical_name_common            'Dimethylglycinium hydrogen squarate'
_chemical_name_systematic        'Dimethylglycine-squaric acid'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 108.249(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.5110(5)
_cell_length_b                   6.5385(2)
_cell_length_c                   17.3475(4)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.13
_cell_measurement_theta_min      2.47
_cell_volume                     1886.32(10)
_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 0.893
_diffrn_measured_fraction_theta_max 0.893
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11666
_diffrn_reflns_theta_full        29.13
_diffrn_reflns_theta_max         29.13
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.956
_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    1.529
_exptl_crystal_density_meas      1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4520
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0609P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1042
_reflns_number_gt                3180
_reflns_number_total             4520
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7054214
_cod_data_source_file            c4nj00212a6.cif
_cod_data_source_block           m
_cod_original_cell_volume        1886.32(9)
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7054322
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'
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
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 .
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
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)
