#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:13:03 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179619 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/83/4508340.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_4508340
loop_
_publ_author_name
'Portell, Anna'
'Font-Bardia, Mercè'
'Prohens, Rafel'
_publ_section_title
;
 Self-Assembling of Zwitterionic Squaramides through Electrostatically
 Compressed Face-to-Face π-Stacking: A New Supramolecular Synthon
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4200
_journal_paper_doi               10.1021/cg401161d
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C8 H12 N2 O3, H2 O'
_chemical_formula_sum            'C8 H14 N2 O4'
_chemical_formula_weight         202.21
_chemical_name_systematic
;
 ?
;
_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                 103.17(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.536(6)
_cell_length_b                   10.844(9)
_cell_length_c                   14.095(11)
_cell_measurement_reflns_used    444
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      3
_cell_volume                     972.7(14)
_computing_cell_refinement       AUTOMAR
_computing_data_collection       MARXDS
_computing_data_reduction        MARSCALE
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      105(2)
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.769
_diffrn_measurement_device_type  'MAR345 with image plate detector'
_diffrn_measurement_method       'phi scan'
_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  0.0917
_diffrn_reflns_av_sigmaI/netI    0.0865
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6841
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.36
_diffrn_reflns_theta_min         2.39
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.121
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2673
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      0.915
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0508P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1135
_refine_ls_wR_factor_ref         0.1260
_reflns_number_gt                1319
_reflns_number_total             2673
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401161d_si_004.cif
_cod_data_source_block           anom66b
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4508340
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
O1 O 0.4039(2) 0.21461(12) 0.02396(10) 0.0498(4) Uani 1 1 d U
O2 O 0.16372(17) 0.43322(12) -0.11544(9) 0.0457(3) Uani 1 1 d .
O3 O 0.6066(2) 0.50826(13) -0.16884(10) 0.0536(4) Uani 1 1 d .
N1 N 0.9338(2) 0.33617(14) 0.20926(11) 0.0403(4) Uani 1 1 d DU
H1N H 0.900(3) 0.4069(12) 0.1750(12) 0.048 Uiso 1 1 d D
N2 N 0.8601(2) 0.31033(14) -0.01300(11) 0.0419(4) Uani 1 1 d DU
H2N H 0.953(2) 0.3483(16) -0.0413(13) 0.050 Uiso 1 1 d D
C1 C 0.7565(3) 0.26714(17) 0.23330(14) 0.0471(5) Uani 1 1 d .
H1A H 0.6665 0.2366 0.1744 0.071 Uiso 1 1 calc R
H1B H 0.6780 0.3209 0.2658 0.071 Uiso 1 1 calc R
H1C H 0.8102 0.1991 0.2752 0.071 Uiso 1 1 calc R
C2 C 1.0762(3) 0.38653(19) 0.30014(14) 0.0497(5) Uani 1 1 d U
H2A H 1.1895 0.4312 0.2831 0.075 Uiso 1 1 calc R
H2B H 1.1320 0.3197 0.3429 0.075 Uiso 1 1 calc R
H2C H 0.9979 0.4408 0.3324 0.075 Uiso 1 1 calc R
C3 C 1.0598(3) 0.25788(17) 0.15385(14) 0.0454(5) Uani 1 1 d .
H3A H 1.1178 0.1879 0.1939 0.054 Uiso 1 1 calc R
H3B H 1.1764 0.3063 0.1421 0.054 Uiso 1 1 calc R
C4 C 0.9301(3) 0.21089(17) 0.05660(14) 0.0433(4) Uani 1 1 d .
H4A H 1.0138 0.1530 0.0290 0.052 Uiso 1 1 calc R
H4B H 0.8083 0.1671 0.0677 0.052 Uiso 1 1 calc R
C5 C 0.6592(3) 0.33803(17) -0.04485(12) 0.0377(4) Uani 1 1 d U
C6 C 0.4607(3) 0.29819(17) -0.02611(13) 0.0404(4) Uani 1 1 d U
C7 C 0.3516(3) 0.39479(17) -0.09107(13) 0.0394(4) Uani 1 1 d .
C8 C 0.5511(3) 0.43092(17) -0.11360(13) 0.0409(4) Uani 1 1 d .
O1W O 0.6385(3) 0.49605(17) 0.37242(15) 0.0861(6) Uani 1 1 d D
H1WA H 0.555(3) 0.512(2) 0.3094(7) 0.103 Uiso 1 1 d D
H1W H 0.629(4) 0.5647(17) 0.4092(13) 0.103 Uiso 1 1 d D
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0475(8) 0.0504(8) 0.0514(8) 0.0050(6) 0.0108(6) -0.0030(6)
O2 0.0416(6) 0.0480(8) 0.0473(8) 0.0035(6) 0.0096(5) 0.0009(6)
O3 0.0501(8) 0.0546(8) 0.0575(9) 0.0074(7) 0.0154(7) 0.0000(6)
N1 0.0435(8) 0.0394(8) 0.0382(8) 0.0034(7) 0.0100(6) 0.0011(6)
N2 0.0407(9) 0.0475(10) 0.0383(8) 0.0018(7) 0.0106(7) -0.0008(7)
C1 0.0514(11) 0.0478(12) 0.0440(11) 0.0017(9) 0.0145(9) -0.0005(8)
C2 0.0511(11) 0.0505(12) 0.0464(10) -0.0017(9) 0.0085(8) -0.0034(9)
C3 0.0422(11) 0.0491(12) 0.0461(11) 0.0022(9) 0.0128(9) 0.0011(8)
C4 0.0447(10) 0.0423(10) 0.0454(11) 0.0001(9) 0.0152(8) 0.0012(8)
C5 0.0361(8) 0.0387(10) 0.0390(9) -0.0009(8) 0.0101(7) -0.0001(7)
C6 0.0382(8) 0.0425(10) 0.0402(10) -0.0014(8) 0.0085(7) -0.0019(7)
C7 0.0384(9) 0.0376(10) 0.0422(10) -0.0004(8) 0.0089(7) 0.0007(7)
C8 0.0402(9) 0.0418(10) 0.0407(10) -0.0003(9) 0.0090(8) 0.0015(8)
O1W 0.0925(12) 0.0782(13) 0.0803(13) -0.0144(10) 0.0046(10) 0.0103(10)
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
C1 N1 C2 110.67(15)
C1 N1 C3 112.30(15)
C2 N1 C3 109.77(15)
C1 N1 H1N 116.3(11)
C2 N1 H1N 100.0(12)
C3 N1 H1N 107.0(12)
C5 N2 C4 122.06(15)
C5 N2 H2N 117.7(13)
C4 N2 H2N 119.8(13)
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N1 C3 C4 113.16(15)
N1 C3 H3A 108.9
C4 C3 H3A 108.9
N1 C3 H3B 108.9
C4 C3 H3B 108.9
H3A C3 H3B 107.8
N2 C4 C3 112.45(16)
N2 C4 H4A 109.1
C3 C4 H4A 109.1
N2 C4 H4B 109.1
C3 C4 H4B 109.1
H4A C4 H4B 107.8
N2 C5 C6 137.09(18)
N2 C5 C8 132.35(16)
C6 C5 C8 90.50(15)
O1 C6 C5 135.23(18)
O1 C6 C7 134.68(18)
C5 C6 C7 90.08(15)
O2 C7 C8 135.14(17)
O2 C7 C6 135.06(17)
C8 C7 C6 89.78(15)
O3 C8 C5 135.05(17)
O3 C8 C7 135.43(17)
C5 C8 C7 89.52(15)
H1WA O1W H1W 106.6(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C6 1.256(2)
O2 C7 1.268(2)
O3 C8 1.253(2)
N1 C1 1.482(2)
N1 C2 1.504(3)
N1 C3 1.517(2)
N1 H1N 0.906(9)
N2 C5 1.322(2)
N2 C4 1.459(2)
N2 H2N 0.898(9)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C3 C4 1.526(3)
C3 H3A 0.9700
C3 H3B 0.9700
C4 H4A 0.9700
C4 H4B 0.9700
C5 C6 1.447(3)
C5 C8 1.463(3)
C6 C7 1.465(3)
C7 C8 1.464(3)
O1W H1WA 0.947(8)
O1W H1W 0.917(9)
