#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:35:40 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178906 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/35/4113580.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_4113580
loop_
_publ_author_name
'Leif Häggman'
'Cecilia Lindblad'
'Hans Oskarsson'
'Ann-Sofi Ullström'
'Ingmar Persson'
_publ_section_title
;
 The Influence of Short Strong Hydrogen Bonding on the Structure and the
 Physicochemical Properties of Alkyl-N-iminodiacetic Acids in Solid State
 and Aqueous Systems
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3631
_journal_page_last               3641
_journal_paper_doi               10.1021/ja021012i
_journal_volume                  125
_journal_year                    2003
_chemical_formula_sum            'C5 H9 N O4'
_chemical_formula_weight         147.13
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.291(6)
_cell_length_b                   10.469(7)
_cell_length_c                   13.489(8)
_cell_measurement_temperature    295(2)
_cell_volume                     1312.0(14)
_computing_cell_refinement       'Bruker Saint Plus'
_computing_data_collection       'Bruker Smart'
_computing_data_reduction        'Bruker Saint Plus'
_computing_molecular_graphics    'Bruker Shelxtl-NT'
_computing_publication_material  'Bruker Shelxtl-NT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart CCD 1k'
_diffrn_measurement_method       'Bruker Smart'
_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  0.1947
_diffrn_reflns_av_sigmaI/netI    0.0966
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5405
_diffrn_reflns_theta_full        23.49
_diffrn_reflns_theta_max         23.49
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       Flake
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0614
_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)+(0.0636P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1421
_reflns_number_gt                652
_reflns_number_total             967
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja021012i_s1_1.cif
_cod_data_source_block           mida2m
_cod_database_code               4113580
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
O2 O 0.1717(3) 0.3612(2) 0.14838(17) 0.0379(8) Uani 1 1 d
O3 O 0.3561(3) 0.4900(3) 0.42267(17) 0.0462(9) Uani 1 1 d
O1 O 0.4085(3) 0.3643(3) 0.17808(16) 0.0411(8) Uani 1 1 d
N1 N 0.3921(3) 0.2478(3) 0.35088(18) 0.0274(8) Uani 1 1 d
O4 O 0.3147(3) 0.4214(3) 0.57603(17) 0.0475(9) Uani 1 1 d
C3 C 0.2846(4) 0.3369(3) 0.1988(2) 0.0294(9) Uani 1 1 d
C4 C 0.3743(5) 0.2689(4) 0.4599(2) 0.0332(10) Uani 1 1 d
C5 C 0.3470(4) 0.4054(4) 0.4832(2) 0.0339(10) Uani 1 1 d
C1 C 0.4541(5) 0.1210(4) 0.3302(3) 0.0378(11) Uani 1 1 d
C2 C 0.2549(4) 0.2664(4) 0.2952(2) 0.0333(10) Uani 1 1 d
H1B H 0.556(5) 0.114(4) 0.360(3) 0.050(12) Uiso 1 1 d
H1C H 0.460(4) 0.113(3) 0.256(3) 0.033(9) Uiso 1 1 d
H2B H 0.213(4) 0.177(4) 0.280(2) 0.040(10) Uiso 1 1 d
H6 H 0.464(4) 0.311(4) 0.330(2) 0.040(11) Uiso 1 1 d
H2A H 0.190(4) 0.314(3) 0.328(2) 0.026(10) Uiso 1 1 d
H4B H 0.465(4) 0.243(3) 0.493(2) 0.025(9) Uiso 1 1 d
H4A H 0.299(4) 0.217(4) 0.483(2) 0.036(11) Uiso 1 1 d
H1A H 0.400(4) 0.060(4) 0.353(2) 0.034(11) Uiso 1 1 d
H22 H 0.303(6) 0.521(5) 0.594(3) 0.085(16) Uiso 1 1 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
O2 0.0369(17) 0.0425(16) 0.0342(13) 0.0115(12) -0.0078(12) -0.0012(13)
O3 0.060(2) 0.0436(17) 0.0346(14) 0.0006(14) 0.0018(13) 0.0047(15)
O1 0.0367(18) 0.0537(18) 0.0330(14) 0.0100(12) 0.0023(12) -0.0098(14)
N1 0.0263(17) 0.0341(19) 0.0220(14) 0.0018(13) 0.0016(13) -0.0015(15)
O4 0.066(2) 0.0455(18) 0.0304(14) -0.0071(13) 0.0133(13) -0.0039(16)
C3 0.036(2) 0.029(2) 0.0232(17) -0.0016(15) 0.0008(19) -0.0020(19)
C4 0.039(3) 0.039(2) 0.0219(18) 0.0027(16) -0.0034(18) 0.004(2)
C5 0.031(2) 0.045(2) 0.0266(19) 0.0030(19) 0.0001(17) -0.0029(19)
C1 0.041(3) 0.031(3) 0.041(2) -0.0048(19) 0.001(2) 0.002(2)
C2 0.029(2) 0.044(2) 0.0273(18) -0.0027(18) -0.0044(18) 0.002(2)
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 110.9(3)
C1 N1 C4 111.2(3)
C2 N1 C4 112.4(3)
O1 C3 O2 127.4(3)
O1 C3 C2 118.8(3)
O2 C3 C2 113.8(3)
C5 C4 N1 111.7(3)
O3 C5 O4 125.0(4)
O3 C5 C4 123.4(3)
O4 C5 C4 111.6(3)
N1 C2 C3 109.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 C3 1.275(4)
O3 C5 1.208(4)
O1 C3 1.219(4)
N1 C1 1.474(5)
N1 C2 1.492(5)
N1 C4 1.496(4)
O4 C5 1.299(4)
C3 C2 1.521(5)
C4 C5 1.485(6)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H6 O2 0.98(4) 2.03(4) 2.857(4) 141(3) 6_656
O4 H22 O2 1.08(6) 1.45(6) 2.480(4) 157(4) 2_565
