#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/07/2210709.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_2210709
loop_
_publ_author_name
'Bai, Guo-Yi'
'Ning, Hui-Sen'
'Simpson, Jim'
'Qin, Xin-Ying'
'Li, Na'
_publ_section_title
;(S,S)-N,N'-Bis(2-hydroxy-2-butyl)ethylenediammonium
 oxalate pentahydrate
;
_journal_coeditor_code           LH2181
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4567
_journal_page_last               o4568
_journal_paper_doi               10.1107/S1600536806037652
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C10 H26 N2 O2 2+, C2 O4 2-, 5H2 O'
_chemical_formula_moiety         'C10 H26 N2 O2 2+, C2 O4 2-, 5H2 O'
_chemical_formula_sum            'C12 H36 N2 O11'
_chemical_formula_weight         384.43
_chemical_name_systematic
;
(S,S)-N,N'-Bis(2-hydroxy-2-butyl)ethylenediammonium oxalate pentahydrate
;
_space_group_IT_number           20
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2104(15)
_cell_length_b                   10.3092(19)
_cell_length_c                   23.771(5)
_cell_measurement_reflns_used    3399
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.6
_cell_volume                     2012.0(7)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12718
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         3.17
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9934
_exptl_absorpt_correction_T_min  0.9762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Jacobson, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.244
_refine_diff_density_min         -0.206
_refine_ls_extinction_coef       0.0137(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0291
_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)+(0.0427P)²+0.473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0712
_reflns_number_gt                1314
_reflns_number_total             1376
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2181.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'C 2c 2 '
_cod_database_code               2210709
_cod_database_fobs_code          2210709
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, -z'
'-x, y, -z+1/2'
'-x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'
'-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
C C1 0.47733(19) 0.39226(15) 0.71864(6) 0.0160(3) Uani d . 1
H H1A 0.4945 0.3045 0.7028 0.019 Uiso calc R 1
H H1B 0.3607 0.4146 0.7143 0.019 Uiso calc R 1
N N1 0.57936(16) 0.48853(13) 0.68705(5) 0.0132(3) Uani d . 1
H H1C 0.596(2) 0.5586(18) 0.7095(8) 0.016 Uiso d . 1
H H1D 0.678(3) 0.4530(18) 0.6815(8) 0.016 Uiso d . 1
C C2 0.51068(19) 0.53964(14) 0.63270(6) 0.0153(3) Uani d . 1
H H2 0.4005 0.5770 0.6405 0.018 Uiso calc R 1
C C3 0.6226(2) 0.64947(15) 0.61306(7) 0.0186(3) Uani d . 1
H H3A 0.6475 0.7065 0.6455 0.022 Uiso calc R 1
H H3B 0.7265 0.6119 0.5996 0.022 Uiso calc R 1
C C4 0.5481(3) 0.73060(19) 0.56624(8) 0.0314(4) Uani d . 1
H H4A 0.4487 0.7726 0.5800 0.047 Uiso calc R 1
H H4B 0.5213 0.6745 0.5343 0.047 Uiso calc R 1
H H4C 0.6262 0.7970 0.5543 0.047 Uiso calc R 1
C C5 0.4916(2) 0.43040(16) 0.59033(7) 0.0184(3) Uani d . 1
H H5A 0.4208 0.3617 0.6061 0.022 Uiso calc R 1
H H5B 0.4399 0.4638 0.5556 0.022 Uiso calc R 1
O O1 0.64811(14) 0.37821(11) 0.57756(5) 0.0191(3) Uani d . 1
H H1 0.638(3) 0.301(2) 0.5686(9) 0.029 Uiso d . 1
C C6 0.58360(17) 0.78537(14) 0.76520(6) 0.0135(3) Uani d . 1
O O2 0.66772(13) 0.68395(10) 0.76030(4) 0.0174(3) Uani d . 1
O O3 0.62101(13) 0.88511(11) 0.79193(5) 0.0207(3) Uani d . 1
O O4 0.8605(2) 0.5000 0.5000 0.0191(3) Uani d S 1
H H4 0.799(3) 0.461(2) 0.5207(9) 0.029 Uiso d . 1
O O5 0.08000(19) 0.58252(15) 0.67537(5) 0.0340(4) Uani d . 1
H H5C 0.152(3) 0.618(2) 0.7015(11) 0.051 Uiso d . 1
H H5D 0.029(4) 0.521(3) 0.6901(11) 0.051 Uiso d . 1
O O6 0.11366(17) 0.62337(12) 0.56322(5) 0.0253(3) Uani d . 1
H H6A 0.092(3) 0.604(2) 0.5984(11) 0.038 Uiso d . 1
H H6B 0.044(3) 0.584(2) 0.5424(10) 0.038 Uiso d . 1
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
N1 C1 C1 . 3_656 110.51(12) yes
C1 N1 C2 . . 116.88(12) yes
C1 N1 H1C . . 108.4(12) yes
C2 N1 H1C . . 106.4(11) ?
C1 N1 H1D . . 107.8(12) ?
C2 N1 H1D . . 110.7(12) ?
H1C N1 H1D . . 106.1(17) ?
N1 C1 H1A . . 109.5 yes
C1 C1 H1A 3_656 . 109.5 ?
N1 C1 H1B . . 109.5 ?
C1 C1 H1B 3_656 . 109.5 ?
H1A C1 H1B . . 108.1 ?
N1 C2 C3 . . 107.19(12) yes
N1 C2 C5 . . 110.39(12) yes
C5 C2 C3 . . 114.09(13) y
N1 C2 H2 . . 108.3 yes
C5 C2 H2 . . 108.3 ?
C3 C2 H2 . . 108.3 y
C4 C3 C2 . . 112.84(14) y
C4 C3 H3A . . 109.0 ?
C2 C3 H3A . . 109.0 ?
C4 C3 H3B . . 109.0 ?
C2 C3 H3B . . 109.0 ?
H3A C3 H3B . . 107.8 ?
C3 C4 H4A . . 109.5 ?
C3 C4 H4B . . 109.5 ?
H4A C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4A C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
O1 C5 C2 . . 109.13(13) ?
O1 C5 H5A . . 109.9 ?
C2 C5 H5A . . 109.9 ?
O1 C5 H5B . . 109.9 ?
C2 C5 H5B . . 109.9 ?
H5A C5 H5B . . 108.3 ?
C5 O1 H1 . . 108.9(17) ?
O3 C6 O2 . . 126.66(13) ?
O3 C6 C6 . 3_656 117.08(10) ?
O2 C6 C6 . 3_656 116.26(9) ?
H5C O5 H5D . . 110(2) ?
H6A O6 H6B . . 108(2) ?
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 C1 3_656 1.537(3) y
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
N1 C1 . 1.5003(19) yes
N1 C2 . 1.5049(19) yes
N1 H1C . 0.908(19) ?
N1 H1D . 0.89(2) ?
C2 C5 . 1.519(2) y
C2 C3 . 1.531(2) y
C2 H2 . 1.0000 ?
C3 C4 . 1.521(2) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
O1 C5 . 1.426(2) y
O1 H1 . 0.82(2) ?
C6 C6 3_656 1.551(3) y
O2 C6 . 1.2584(17) y
O3 C6 . 1.2472(18) y
O4 H4 . 0.81(2) ?
O5 H5C . 0.93(3) ?
O5 H5D . 0.84(3) ?
O6 H6A . 0.88(3) ?
O6 H6B . 0.86(3) ?
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
O4 H4 O1 . 0.81(2) 2.02(2) 2.8314(16) 174(2)
N1 H1C O2 . 0.908(19) 1.86(2) 2.7599(17) 168.3(17)
N1 H1C O2 3_656 0.908(19) 2.622(19) 3.1210(17) 115.4(15)
N1 H1D O3 7_646 0.89(2) 1.90(2) 2.7273(17) 152.1(17)
O5 H5C O2 3_656 0.93(3) 1.87(3) 2.7789(18) 166(2)
O5 H5D O3 7_546 0.84(3) 1.91(3) 2.7330(18) 166(3)
O6 H6A O5 . 0.88(3) 1.85(3) 2.7132(18) 169(2)
O1 H1 O6 5_545 0.82(2) 1.85(2) 2.6643(17) 169(2)
O6 H6B O4 1_455 0.86(3) 2.01(3) 2.8630(18) 173(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_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 C1 C1 3_656 -156.35(12) yes
C1 N1 C2 C5 . -63.45(16) yes
C1 N1 C2 C3 . 171.74(12) yes
N1 C2 C3 C4 . -166.73(13) yes
C5 C2 C3 C4 . 70.74(18) ?
N1 C2 C5 O1 . -63.06(16) yes
C3 C2 C5 O1 . 57.72(16) ?
