#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006513.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_2006513
loop_
_publ_author_name
'Lo, J.-M.'
'Yao, H.-H.'
'Lu, T.-H.'
_publ_section_title
;
 <i>N</i>,<i>N</i>'-Bis(2-hydroxybenzyl)-1,4-butanediammonium Dinitrate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1327
_journal_page_last               1329
_journal_volume                  53
_journal_year                    1997
_chemical_formula_iupac          'C18 H26 N2 O2 2+ , 2N O3 -'
_chemical_formula_moiety         'C18 H26 N4 O8 '
_chemical_formula_sum            'C18 H26 N4 O8'
_chemical_formula_weight         426.42
_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'
_cell_angle_alpha                90.0
_cell_angle_beta                 115.486(8)
_cell_angle_gamma                90.0
_cell_formula_units_Z            2
_cell_length_a                   8.6351(8)
_cell_length_b                   15.6177(10)
_cell_length_c                   8.8929(15)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    293
_cell_measurement_theta_max      12.08
_cell_measurement_theta_min      5.79
_cell_volume                     1082.6(2)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
'NRCVAX DATRD2 (Gabe, Le Page, Charland, Lee & White, 1989)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976) in NRCVAX'
_computing_publication_material  'NRCVAX TABLES Jan 94 Version'
_computing_structure_refinement  'NRCVAX LSTSQ'
_computing_structure_solution    'NRCVAX SOLVER'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Nonius CAD-4    '
_diffrn_measurement_method       '\q/2\q scan b/P/b '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'xray tube'
_diffrn_radiation_type           'Molybdenum K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.013
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2038
_diffrn_reflns_theta_max         24.92
_diffrn_reflns_theta_min         0.00
_diffrn_standards_decay_%        1.0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.10
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Light brown'
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       Pillar
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.15
_refine_ls_extinction_coef       80E2(19)
_refine_ls_extinction_method     'Larson (1970)'
_refine_ls_goodness_of_fit_obs   1.21
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1324
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_obs          0.042
_refine_ls_shift/esd_max         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     1/[\s^2^(F)+0.0005F^2^]
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.049
_refine_ls_wR_factor_obs         0.048
_reflns_number_observed          1329
_reflns_number_total             1908
_reflns_observed_criterion       'Inet > 1.0\s(Inet)'
_[local]_cod_data_source_file    ln1002.cif
_[local]_cod_data_source_block   I
_[local]_cod_chemical_formula_sum_orig 'C18 H26 N4 O8 '
_cod_database_code               2006513
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,1/2+y,1/2-z
x,1/2-y,1/2+z
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
_atom_site_aniso_type_symbol
O1 0.0689(12) 0.0438(9) 0.0583(11) -0.0145(8) 0.0356(9) -0.0066(8) O
O2 0.0887(14) 0.0411(9) 0.0661(11) -0.0211(9) 0.0513(10) -0.0208(8) O
O3 0.1007(15) 0.0550(11) 0.0590(11) -0.0136(10) 0.0552(11) -0.0178(9) O
O 0.0498(10) 0.0512(10) 0.0544(10) -0.0086(8) 0.0225(9) 0.0066(8) O
N1 0.0380(10) 0.0300(9) 0.0385(10) 0.0008(8) 0.0188(8) 0.0023(8) N
N2 0.0496(12) 0.0333(10) 0.0391(10) 0.0010(9) 0.0188(9) -0.0010(9) N
C1 0.0406(14) 0.0450(13) 0.0389(12) -0.0050(11) 0.0146(11) -0.0080(11) C
C2 0.0427(16) 0.0791(19) 0.0575(16) -0.0092(14) 0.0231(13) -0.0097(15) C
C3 0.0396(16) 0.100(2) 0.072(2) 0.0129(16) 0.0138(15) -0.0108(19) C
C4 0.0587(19) 0.076(2) 0.0643(18) 0.0169(16) 0.0100(16) 0.0075(16) C
C5 0.0521(17) 0.0571(16) 0.0485(15) 0.0022(13) 0.0154(14) 0.0048(12) C
C6 0.0389(13) 0.0400(12) 0.0366(12) -0.0005(10) 0.0150(10) -0.0052(10) C
C7 0.0446(13) 0.0380(12) 0.0390(12) -0.0003(10) 0.0210(11) -0.0029(10) C
C8 0.0361(12) 0.0401(12) 0.0494(13) 0.0016(10) 0.0188(11) 0.0069(11) C
C9 0.0363(13) 0.0442(13) 0.0492(13) 0.0092(10) 0.0209(11) 0.0083(11) C
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_type_symbol
O1 0.8219(2) 0.22205(10) 0.13337(19) 0.0541(11) Uani O
O2 0.6784(2) 0.10531(10) 0.0950(2) 0.0589(12) Uani O
O3 0.6973(3) 0.19286(11) 0.2900(2) 0.0643(13) Uani O
O 0.48880(2) 0.00724(10) 0.20766(19) 0.0517(11) Uani O
N1 0.2184(2) -0.12562(10) 0.1725(2) 0.0347(11) Uani N
N2 0.7331(2) 0.17424(11) 0.1733(2) 0.0408(12) Uani N
C1 0.5868(3) -0.04986(14) 0.3250(3) 0.0424(14) Uani C
C2 0.7612(3) -0.06051(19) 0.3731(3) 0.0592(18) Uani C
C3 0.8508(3) -0.1194(2) 0.4942(4) 0.074(2) Uani C
C4 0.7708(4) -0.1674(2) 0.5691(4) 0.072(2) Uani C
C5 0.5971(3) -0.15759(16) 0.5206(3) 0.0548(17) Uani C
C6 0.5034(3) -0.09920(14) 0.3979(3) 0.0389(13) Uani C
C7 0.3155(3) -0.08715(13) 0.3417(3) 0.0395(13) Uani C
C8 0.0285(3) -0.11397(14) 0.0988(3) 0.0417(14) Uani C
C9 -0.0279(3) -0.02148(14) 0.0608(3) 0.0424(14) Uani C
H 0.549 0.0417 0.175 0.068 Uiso H
Hn1 0.259 -0.1044 0.101 0.037 Uiso H
Hn2 0.235 -0.1856 0.180 0.055 Uiso H
H2 0.815 -0.0241 0.324 0.063 Uiso H
H3 0.963 -0.1277 0.526 0.089 Uiso H
H4 0.833 -0.209 0.654 0.100 Uiso H
H5 0.535 -0.1918 0.570 0.060 Uiso H
H7a 0.274 -0.1166 0.417 0.040 Uiso H
H7b 0.284 -0.0282 0.329 0.038 Uiso H
H8a -0.020 -0.1494 -0.006 0.047 Uiso H
H8b -0.013 -0.1389 0.174 0.047 Uiso H
H9a -0.152 -0.0223 0.019 0.050 Uiso H
H9b 0.017 0.0132 0.163 0.049 Uiso H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O 0.008 0.006 'International Tables Vol. IV Table 2.2B'
N 0.004 0.003 'International Tables Vol. IV Table 2.2B'
C 0.002 0.002 'International Tables Vol. IV Table 2.2B'
H 0.000 0.000 'International Tables Vol. IV Table 2.2B'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 2 0
-3 1 0
1 5 -1
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
C1 O H ? ? 113.2(17) no
C7 N1 C8 ? ? 115.28(16) yes
C7 N1 Hn1 ? ? 109.7 no
C7 N1 Hn2 ? ? 108.9 no
C8 N1 Hn1 ? ? 109.3 no
C8 N1 Hn2 ? ? 105.1 no
Hn1 N1 Hn2 ? ? 108.3 no
O1 N2 O2 ? ? 119.56(18) yes
O1 N2 O3 ? ? 120.79(18) yes
O2 N2 O3 ? ? 119.66(19) yes
O C1 C2 ? ? 123.5(2) yes
O C1 C6 ? ? 116.5(2) yes
C2 C1 C6 ? ? 120.1(2) no
C1 C2 C3 ? ? 119.5(3) no
C1 C2 H2 ? ? 117.9 no
C3 C2 H2 ? ? 122.4 no
C2 C3 C4 ? ? 121.0(3) no
C2 C3 H3 ? ? 121.2 no
C4 C3 H3 ? ? 117.8 no
C3 C4 C5 ? ? 119.6(3) no
C3 C4 H4 ? ? 121. no
C5 C4 H4 ? ? 119. no
C4 C5 C6 ? ? 120.5(3) no
C4 C5 H5 ? ? 121.8 no
C6 C5 H5 ? ? 117.6 no
C1 C6 C5 ? ? 119.2(2) no
C1 C6 C7 ? ? 118.80(19) no
C5 C6 C7 ? ? 122.0(2) no
N1 C7 C6 ? ? 110.14(17) yes
N1 C7 H7a ? ? 106.4 no
N1 C7 H7b ? ? 105.2 no
C6 C7 H7a ? ? 111.8 no
C6 C7 H7b ? ? 112.3 no
H7a C7 H7b ? ? 110.6 no
N1 C8 C9 ? ? 113.66(17) yes
N1 C8 H8a ? ? 106.2 no
N1 C8 H8b ? ? 108.1 no
C9 C8 H8a ? ? 110.6 no
C9 C8 H8b ? ? 111.0 no
H8a C8 H8b ? ? 107.0 no
C8 C9 C9 ? 2 114.21(18) no
C8 C9 H9a ? ? 105.6 no
C8 C9 H9b ? ? 110.9 no
C9 C9 H9a 2 ? 111.7 no
C9 C9 H9b 2 ? 107.4 no
H9a C9 H9b ? ? 106.8 no
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
O1 N2 ? 1.227(3) yes
O2 N2 ? 1.258(2) yes
O3 N2 ? 1.238(3) yes
O C1 ? 1.357(3) yes
O H ? 0.88(3) no
N1 C7 ? 1.498(3) yes
N1 C8 ? 1.492(3) yes
N1 Hn1 ? 0.91 no
N1 Hn2 ? 0.95 no
C1 C2 ? 1.387(4) no
C1 C6 ? 1.391(3) no
C2 C3 ? 1.373(4) no
C2 H2 ? 0.95 no
C3 C4 ? 1.371(5) no
C3 H3 ? 0.89 no
C4 C5 ? 1.380(4) no
C4 H4 ? 0.96 no
C5 C6 ? 1.385(3) no
C5 H5 ? 0.98 no
C6 C7 ? 1.490(3) no
C7 H7a ? 1.00 no
C7 H7b ? 0.95 no
C8 C9 ? 1.516(3) no
C8 H8a ? 1.01 no
C8 H8b ? 0.97 no
C9 C9 2 1.517(4) no
C9 H9a ? 0.97 no
C9 H9b ? 0.99 no
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
_geom_hbond_publ_flag
O H O2 . 0.88 1.85 2.728(2) 174 yes
N1 Hn1 O . 0.91 2.50 3.038(2) 118 yes
N1 Hn1 O1 2_655 0.91 2.64 2.996(2) 104 yes
N1 Hn1 O2 2_655 0.91 2.04 2.894(3) 156 yes
N1 Hn2 O1 3_645 0.95 2.41 3.046(2) 125 yes
N1 Hn2 O3 3_645 0.95 1.96 2.910(2) 172 yes
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
C8 N1 C7 C6 . -177.2(4)
O C1 C2 C3 . 179.4(5)
O C1 C6 C5 . -178.9(4)
C2 C1 C6 C5 . 1.2(2)
C1 C2 C3 C4 . -0.4(2)
C3 C4 C5 C6 . -0.5(2)
C4 C5 C6 C7 . 179.7(5)
C5 C6 C7 N1 . -106.8(4)
N1 C8 C9 C9 2 59.5(3)
C7 N1 C8 C9 . 65.6(3)
C6 C1 C2 C3 . -0.7(2)
O C1 C6 C7 . 0.82(16)
C2 C1 C6 C7 . -179.1(4)
C2 C3 C4 C5 . 1.0(2)
C4 C5 C6 C1 . -0.6(2)
C1 C6 C7 N1 . 73.5(3)