#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/99/2219945.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_2219945
loop_
_publ_author_name
'Bai, Hong-Ye'
'Liu, Hai-Yan'
'Ma, Jian-Fang'
_publ_section_title
;N,N'-Bis(2-hydroxyethyl)-N,N'-[ethylenedioxybis(o-phenylenemethylene)]diammonium
 fumarate tetrahydrate
;
_journal_coeditor_code           NC2116
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2162
_journal_paper_doi               10.1107/S1600536808033746
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C20 H30 N2 O4 2+ , C4 H2 O4 2- , 4H2 O'
_chemical_formula_moiety         'C20 H30 N2 O4 2+ , C4 H2 O4 2- , 4H2 O'
_chemical_formula_sum            'C24 H40 N2 O12'
_chemical_formula_weight         548.58
_chemical_name_systematic
;
N,N'-Bis(2-hydroxyethyl)-N,N'-[ethylenedioxybis(o-\
phenylenemethylene)]diammonium fumarate tetrahydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                104.64(2)
_cell_angle_beta                 96.77(3)
_cell_angle_gamma                104.29(3)
_cell_formula_units_Z            1
_cell_length_a                   7.585(7)
_cell_length_b                   8.623(6)
_cell_length_c                   11.515(7)
_cell_measurement_reflns_used    3128
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     693.0(9)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6826
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             294
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3128
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0450
_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)+(0.0619P)²+0.1182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                2394
_reflns_number_total             3128
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2116.cif
_cod_data_source_block           I
_cod_database_code               2219945
_cod_database_fobs_code          2219945
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.4884(2) 0.33265(18) 0.58122(12) 0.0353(3) Uani d . 1
C C2 0.3124(2) 0.2213(2) 0.54836(15) 0.0470(4) Uani d . 1
H H2 0.2257 0.2368 0.5977 0.056 Uiso calc R 1
C C3 0.2632(3) 0.0871(2) 0.44313(17) 0.0582(5) Uani d . 1
H H3 0.1438 0.0140 0.4212 0.070 Uiso calc R 1
C C4 0.3923(3) 0.0628(2) 0.37144(15) 0.0576(5) Uani d . 1
H H4 0.3599 -0.0284 0.3015 0.069 Uiso calc R 1
C C5 0.5695(3) 0.1718(2) 0.40173(14) 0.0507(4) Uani d . 1
H H5 0.6560 0.1539 0.3528 0.061 Uiso calc R 1
C C6 0.6173(2) 0.3083(2) 0.50592(12) 0.0388(3) Uani d . 1
C C7 0.5438(2) 0.48184(19) 0.69256(13) 0.0381(3) Uani d . 1
H H7A 0.5907 0.5822 0.6688 0.046 Uiso calc R 1
H H7B 0.4355 0.4914 0.7277 0.046 Uiso calc R 1
C C8 0.7528(2) 0.61530(18) 0.90008(13) 0.0406(3) Uani d . 1
H H8A 0.8408 0.5931 0.9574 0.049 Uiso calc R 1
H H8B 0.6472 0.6266 0.9380 0.049 Uiso calc R 1
C C9 0.8425(2) 0.77871(19) 0.87634(15) 0.0471(4) Uani d . 1
H H9A 0.7507 0.8081 0.8269 0.056 Uiso calc R 1
H H9B 0.8863 0.8665 0.9536 0.056 Uiso calc R 1
C C10 0.9210(2) 0.4234(2) 0.46928(15) 0.0532(4) Uani d . 1
H H10A 0.8711 0.4244 0.3880 0.064 Uiso calc R 1
H H10B 0.9610 0.3235 0.4623 0.064 Uiso calc R 1
C C11 0.6218(2) 0.21555(18) 0.97927(15) 0.0403(3) Uani d . 1
C C12 0.5574(2) 0.07174(19) 1.03092(14) 0.0431(4) Uani d . 1
H H12 0.6033 0.0873 1.1129 0.052 Uiso calc R 1
O O1 0.78557(15) 0.42777(16) 0.54483(10) 0.0503(3) Uani d . 1
O O2 0.52895(15) 0.21994(13) 0.88286(10) 0.0485(3) Uani d . 1
O O3 0.76640(19) 0.32235(16) 1.03867(13) 0.0684(4) Uani d . 1
O O1W 0.0354(2) 0.3790(2) 0.77573(13) 0.0646(4) Uani d . 1
H H1C 0.050(4) 0.289(4) 0.787(2) 0.097 Uiso d . 1
H H1D 0.122(4) 0.462(4) 0.836(3) 0.097 Uiso d . 1
O O2W 0.1427(2) 0.09631(18) 0.79075(15) 0.0672(4) Uani d . 1
H H2C 0.260(5) 0.129(4) 0.818(3) 0.101 Uiso d . 1
H H2D 0.101(4) -0.004(4) 0.795(3) 0.101 Uiso d . 1
O O4 0.99312(17) 0.76942(15) 0.81566(12) 0.0521(3) Uani d . 1
H H4A 1.073(3) 0.739(3) 0.860(2) 0.078 Uiso d . 1
N N5 0.68936(17) 0.46959(14) 0.78706(10) 0.0310(3) Uani d . 1
H H5A 0.792(3) 0.458(2) 0.7581(16) 0.046 Uiso d . 1
H H5B 0.638(2) 0.374(2) 0.8117(15) 0.046 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 0.0016 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C6 . . 118.93(15)
C2 C1 C7 . . 122.15(14)
C6 C1 C7 . . 118.89(14)
C1 C2 C3 . . 120.98(17)
C1 C2 H2 . . 119.5
C3 C2 H2 . . 119.5
C4 C3 C2 . . 119.45(18)
C4 C3 H3 . . 120.3
C2 C3 H3 . . 120.3
C3 C4 C5 . . 121.00(17)
C3 C4 H4 . . 119.5
C5 C4 H4 . . 119.5
C4 C5 C6 . . 119.42(17)
C4 C5 H5 . . 120.3
C6 C5 H5 . . 120.3
O1 C6 C5 . . 125.51(15)
O1 C6 C1 . . 114.30(14)
C5 C6 C1 . . 120.19(16)
N5 C7 C1 . . 112.04(12)
N5 C7 H7A . . 109.2
C1 C7 H7A . . 109.2
N5 C7 H7B . . 109.2
C1 C7 H7B . . 109.2
H7A C7 H7B . . 107.9
N5 C8 C9 . . 113.42(13)
N5 C8 H8A . . 108.9
C9 C8 H8A . . 108.9
N5 C8 H8B . . 108.9
C9 C8 H8B . . 108.9
H8A C8 H8B . . 107.7
O4 C9 C8 . . 112.16(13)
O4 C9 H9A . . 109.2
C8 C9 H9A . . 109.2
O4 C9 H9B . . 109.2
C8 C9 H9B . . 109.2
H9A C9 H9B . . 107.9
O1 C10 C10 . 2_766 105.74(17)
O1 C10 H10A . . 110.6
C10 C10 H10A 2_766 . 110.6
O1 C10 H10B . . 110.6
C10 C10 H10B 2_766 . 110.6
H10A C10 H10B . . 108.7
O3 C11 O2 . . 125.21(14)
O3 C11 C12 . . 114.98(14)
O2 C11 C12 . . 119.81(14)
C12 C12 C11 2_657 . 124.47(19)
C12 C12 H12 2_657 . 117.8
C11 C12 H12 . . 117.8
C6 O1 C10 . . 118.86(13)
H1C O1W H1D . . 104(2)
H2C O2W H2D . . 108(3)
C9 O4 H4A . . 108.2(15)
C8 N5 C7 . . 114.91(12)
C8 N5 H5A . . 106.3(11)
C7 N5 H5A . . 112.5(11)
C8 N5 H5B . . 106.9(10)
C7 N5 H5B . . 107.6(10)
H5A N5 H5B . . 108.3(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.383(2)
C1 C6 . 1.400(2)
C1 C7 . 1.499(2)
C2 C3 . 1.385(3)
C2 H2 . 0.9300
C3 C4 . 1.374(3)
C3 H3 . 0.9300
C4 C5 . 1.383(3)
C4 H4 . 0.9300
C5 C6 . 1.389(2)
C5 H5 . 0.9300
C6 O1 . 1.369(2)
C7 N5 . 1.499(2)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 N5 . 1.494(2)
C8 C9 . 1.513(2)
C8 H8A . 0.9700
C8 H8B . 0.9700
C9 O4 . 1.416(2)
C9 H9A . 0.9700
C9 H9B . 0.9700
C10 O1 . 1.424(2)
C10 C10 2_766 1.492(4)
C10 H10A . 0.9700
C10 H10B . 0.9700
C11 O3 . 1.235(2)
C11 O2 . 1.257(2)
C11 C12 . 1.508(2)
C12 C12 2_657 1.293(3)
C12 H12 . 0.9300
O1W H1C . 0.85(3)
O1W H1D . 0.91(3)
O2W H2C . 0.85(3)
O2W H2D . 0.86(3)
O4 H4A . 0.88(3)
N5 H5A . 0.900(19)
N5 H5B . 0.950(19)
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
O1W H1C O2W . 0.85(3) 1.97(3) 2.792(3) 164(3)
O2W H2C O2 . 0.85(3) 1.97(3) 2.828(3) 176(3)
N5 H5B O2 . 0.950(19) 1.811(19) 2.749(2) 168.6(16)
O1W H1D O3 2_667 0.91(3) 1.96(3) 2.830(3) 159(3)
O2W H2D O4 1_445 0.86(3) 2.01(3) 2.867(3) 175(3)
N5 H5A O1W 1_655 0.900(19) 2.125(19) 2.925(3) 147.6(15)
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_1
_geom_torsion_site_symmetry_4
_geom_torsion
C6 C1 C2 C3 . . 0.3(2)
C7 C1 C2 C3 . . 178.16(14)
C1 C2 C3 C4 . . 1.1(3)
C2 C3 C4 C5 . . -1.0(3)
C3 C4 C5 C6 . . -0.3(3)
C4 C5 C6 O1 . . -178.31(14)
C4 C5 C6 C1 . . 1.6(2)
C2 C1 C6 O1 . . 178.34(12)
C7 C1 C6 O1 . . 0.37(18)
C2 C1 C6 C5 . . -1.6(2)
C7 C1 C6 C5 . . -179.58(13)
C2 C1 C7 N5 . . 114.29(16)
C6 C1 C7 N5 . . -67.81(17)
N5 C8 C9 O4 . . -55.82(19)
O3 C11 C12 C12 . 2_657 -160.5(2)
O2 C11 C12 C12 . 2_657 19.9(3)
C5 C6 O1 C10 . . 5.5(2)
C1 C6 O1 C10 . . -174.42(13)
C10 C10 O1 C6 2_766 . 174.87(16)
C9 C8 N5 C7 . . -61.95(18)
C1 C7 N5 C8 . . 179.32(12)
