#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:48:21 +0200 (vie 13 de oct de 2017) $
#$Revision: 201957 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/77/2017742.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2017742
loop_
_publ_author_name
'Wiklund, Tove'
'McKenzie, Christine J.'
'Lennartson, Anders'
_publ_section_title
;
 Graphene-like nets of hydrogen-bonded water molecules in the dihydrate
 of 2-[(2-ammonioethyl)amino]acetate and the structure of its anhydrous
 hydroiodide salt
;
_journal_coeditor_code           DN3147
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o410
_journal_page_last               o413
_journal_paper_doi               10.1107/S0108270110026314
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C4 H10 N2 O2 , 2H2 O'
_chemical_formula_moiety         'C4 H10 N2 O2 , 2H2 O'
_chemical_formula_sum            'C4 H14 N2 O4'
_chemical_formula_weight         154.17
_chemical_name_common            'N-(β-aminoethyl)glycine dihydrate'
_chemical_name_systematic
;
2-[(2-ammonioethyl)amino]acetate dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.154(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.7106(4)
_cell_length_b                   22.8634(19)
_cell_length_c                   7.2804(6)
_cell_measurement_reflns_used    4911
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.96
_cell_volume                     776.17(11)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLUTON (Spek, 2009)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1993)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker X8 APEXII CCD area-detector'
_diffrn_measurement_method       'thin-slice ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13219
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.56
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9818
_exptl_absorpt_correction_T_min  0.8767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.218
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1521
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0293
_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)+(0.0648P)²+0.0169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0884
_reflns_number_gt                1246
_reflns_number_total             1521
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn3147.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2017742
_cod_database_fobs_code          2017742
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.1610(2) 0.57171(5) 0.74596(14) 0.0125(3) Uani d . 1 . .
C C2 0.0526(2) 0.60999(5) 0.66356(15) 0.0139(3) Uani d . 1 . .
H H2A -0.0202 0.6507 0.6549 0.017 Uiso calc R 1 . .
H H2B 0.2365 0.6100 0.7484 0.017 Uiso calc R 1 . .
C C3 0.3015(2) 0.63178(5) 0.40600(15) 0.0134(3) Uani d . 1 . .
H H3A 0.4794 0.6351 0.4959 0.016 Uiso calc R 1 . .
H H3B 0.2111 0.6709 0.3932 0.016 Uiso calc R 1 . .
C C4 0.3791(2) 0.61330(5) 0.22016(15) 0.0152(3) Uani d . 1 . .
H H4A 0.2018 0.6023 0.1375 0.018 Uiso calc R 1 . .
H H4B 0.4658 0.6470 0.1631 0.018 Uiso calc R 1 . .
N N1 0.10538(19) 0.59101(4) 0.48008(12) 0.0119(2) Uani d . 1 . .
N N2 0.5835(2) 0.56308(4) 0.23365(14) 0.0136(2) Uani d . 1 . .
O O1 -0.25969(18) 0.52766(4) 0.65803(11) 0.0212(2) Uani d . 1 . .
O O2 -0.22566(16) 0.58825(3) 0.90082(10) 0.0170(2) Uani d . 1 . .
O O3 -0.19371(18) 0.70606(4) 0.97998(12) 0.0195(2) Uani d . 1 . .
O O4 0.2679(2) 0.75396(4) 0.84425(14) 0.0235(2) Uani d . 1 . .
H H1N 0.496(3) 0.5284(7) 0.264(2) 0.032(4) Uiso d . 1 . .
H H1W -0.054(4) 0.7204(7) 0.931(2) 0.036(4) Uiso d . 1 . .
H H2N 0.646(3) 0.5595(6) 0.120(2) 0.025(4) Uiso d . 1 . .
H H2W -0.191(3) 0.6686(9) 0.955(2) 0.044(5) Uiso d . 1 . .
H H3N 0.752(3) 0.5712(7) 0.320(2) 0.030(4) Uiso d . 1 . .
H H3W 0.437(4) 0.7387(7) 0.883(2) 0.043(5) Uiso d . 1 . .
H H4N 0.177(3) 0.5557(6) 0.4911(17) 0.017(3) Uiso d . 1 . .
H H4W 0.279(4) 0.7653(8) 0.727(3) 0.055(5) Uiso d . 1 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0120(5) 0.0133(6) 0.0122(6) 0.0024(4) 0.0017(4) 0.0016(4)
C2 0.0133(5) 0.0172(6) 0.0119(5) -0.0015(5) 0.0038(4) -0.0022(4)
C3 0.0125(5) 0.0124(6) 0.0161(6) -0.0013(4) 0.0050(4) 0.0013(4)
C4 0.0141(5) 0.0176(6) 0.0146(6) -0.0001(4) 0.0041(4) 0.0036(5)
N1 0.0135(5) 0.0114(5) 0.0118(5) -0.0003(4) 0.0053(4) 0.0003(4)
N2 0.0149(5) 0.0156(5) 0.0113(5) -0.0022(4) 0.0053(4) -0.0005(4)
O1 0.0287(5) 0.0170(5) 0.0207(4) -0.0085(4) 0.0125(4) -0.0049(3)
O2 0.0195(4) 0.0206(5) 0.0123(4) -0.0022(3) 0.0070(3) -0.0009(3)
O3 0.0199(5) 0.0181(5) 0.0221(5) -0.0015(4) 0.0089(4) -0.0013(4)
O4 0.0187(5) 0.0261(5) 0.0267(5) -0.0004(4) 0.0066(4) 0.0055(4)
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 O2 . . 125.35(10) ?
O1 C1 C2 . . 118.81(9) ?
O2 C1 C2 . . 115.84(9) ?
N1 C2 C1 . . 113.49(9) ?
N1 C2 H2A . . 108.9 ?
C1 C2 H2A . . 108.9 ?
N1 C2 H2B . . 108.9 ?
C1 C2 H2B . . 108.9 ?
H2A C2 H2B . . 107.7 ?
N1 C3 C4 . . 113.34(9) ?
N1 C3 H3A . . 108.9 ?
C4 C3 H3A . . 108.9 ?
N1 C3 H3B . . 108.9 ?
C4 C3 H3B . . 108.9 ?
H3A C3 H3B . . 107.7 ?
N2 C4 C3 . . 113.07(9) ?
N2 C4 H4A . . 109.0 ?
C3 C4 H4A . . 109.0 ?
N2 C4 H4B . . 109.0 ?
C3 C4 H4B . . 109.0 ?
H4A C4 H4B . . 107.8 ?
C2 N1 C3 . . 110.22(9) ?
C2 N1 H4N . . 107.8(8) ?
C3 N1 H4N . . 111.3(9) ?
C4 N2 H1N . . 111.5(9) ?
C4 N2 H2N . . 107.2(9) ?
H1N N2 H2N . . 110.1(13) ?
C4 N2 H3N . . 111.2(9) ?
H1N N2 H3N . . 111.3(12) ?
H2N N2 H3N . . 105.2(12) ?
H1W O3 H2W . . 104.7(15) ?
H3W O4 H4W . . 104.1(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.2474(14) ?
C1 O2 . 1.2667(13) ?
C1 C2 . 1.5195(16) ?
C2 N1 . 1.4590(14) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 N1 . 1.4679(14) ?
C3 C4 . 1.5109(15) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 N2 . 1.4927(15) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
N1 H4N . 0.875(14) ?
N2 H1N . 0.934(17) ?
N2 H2N . 0.924(16) ?
N2 H3N . 0.958(15) ?
O3 H1W . 0.856(19) ?
O3 H2W . 0.87(2) ?
O4 H3W . 0.878(19) ?
O4 H4W . 0.90(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H1N O1 3_566 0.929(17) 1.843(17) 2.7557(13) 166.7(13)
O3 H1W O4 1_555 0.852(19) 1.893(19) 2.7413(13) 174.2(15)
N2 H2N O2 1_654 0.932(15) 1.891(16) 2.7614(13) 154.5(13)
O3 H2W O2 1_555 0.88(2) 1.88(2) 2.7541(13) 173.9(15)
N2 H3N N1 1_655 0.958(15) 1.946(15) 2.9018(13) 176.0(12)
O4 H3W O3 1_655 0.884(19) 1.927(19) 2.8102(13) 177.3(15)
N1 H4N O1 3_566 0.875(14) 2.256(14) 3.0179(13) 145.4(11)
O4 H4W O3 4_675 0.91(2) 1.93(2) 2.8345(14) 177.1(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654251
