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###                                                                        ###
###           Electronic papers (Acta Crystallographica Section C)         ###
###                                                                        ###
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# This paper is published electronically. It meets the data-validation       #
# criteria for publication in Acta Crystallographica Section C.              #
# The submission has been checked by a Section C Co-editor though the text   #
# in _publ_section_comments is the responsibility of the authors.            #
#                                                                            #
# Electronic papers are listed in the printed contents pages of an issue of  #
# Acta Crystallographica Section C within two months of acceptance and are   #
# available by email and via the online contents pages for that issue.       #
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# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     'by teXsan'
_journal_data_validation_number     IUC0000125
_journal_date_recd_electronic     2000-02-17
_journal_date_accepted     2000-04-20
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2000
_journal_volume     56
_journal_issue      6
_journal_page_first     e260
_journal_page_last     e261
_journal_paper_category     CO
_publ_contact_author_name     'Dr Shigeru Ohba'
_publ_contact_author_address
;
Department of Chemistry
Faculty of Science of Technology
Keio University
Hiyoshi 3-14-1
Kohoku-ku
Yokohama 223-8522
Japan
;
_publ_contact_author_email     ohba@chem.keio.ac.jp
_publ_contact_author_fax     '(81) 45 563 5967'
_publ_contact_author_phone     '(81) 45 563 1141 ext 3912'
_publ_section_title
;
1,3-Propanediammonium bis(3'-nitro-trans-cinnamate) and
trans-1,2-cyclohexanediammonium bis(3'-nitro-trans-cinnamate)
;
loop_
    _publ_author_name
    _publ_author_address
    'Hosomi, Hiroyuki'
;
Department of Chemistry
Faculty of Science and Technology
Keio University
Hiyoshi 3-14-1, Kohoku-ku
Yokohama 223-8522
Japan
;
    'Ohba, Shigeru'
;
Department of Chemistry
Faculty of Science and Technology
Keio University
Hiyoshi 3-14-1, Kohoku-ku
Yokohama 223-8522
Japan
;
    'Ito, Yoshikatsu'
;
Department of Synthetic Chemistry and Biological Chemistry
Graduate School of Engineering
Kyoto University
Kyoto 606-8501
Japan
;
_publ_section_synopsis
;
In the two title adducts, (I) and (II), respectively, hydrogen bonds between
the diammonium and carboxylate ions form a two-dimensional network parallel
to the ab plane in (I) and one-dimensional chains along the c axis in (II).
;
_publ_section_abstract
;
In the title two adducts, C₃H₁₂N₂²⁺.2C₉H₆NO₄⁻, (I),
and C₆H₁₆N₂²⁺.2C₉H₆NO₄⁻, (II), hydrogen bonds between the
diammonium and carboxylate ions form a two-dimensional network parallel to
the ab plane in (I) and one-dimensional chains along the c axis in (II).
The cyclohexanediammonium ion in (II) has a crystallographic twofold axis.
;
_publ_section_comment
;
The crystal structure and photoreactivity of ethylenediammonium
bis(3'-nitro-trans-cinnnamate) was reported by Ito et al. (1995).
The structures of 1,3-propanediammonium bis(3'-nitro-trans-cinnamate)
{IUPAC name: propane-1,3-diammonium bis[(E)-3-(3-nitrophenyl)propenoate]},
(I), and trans-1,2-cyclohexanediammonium bis(3'-nitro-trans-cinnamate)
{IUPAC name: trans-cyclohexane-1,2-diammonium
bis[(E)-3-(3-nitrophenyl)propenoate]}, (II), are reported here.
;
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A.,
Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Ito, Y., Borecka, B., Olovsson, G., Trotter, J. & Scheffer, J. R.
(1995). Tetrahedron Lett. 36, 6087-6090.
Molecular Structure Corporation. (1993). MSC/AFC Diffractometer Control
Software. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Molecular Structure Corporation. (1999). TEXSAN. Version 1.10.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.
Sheldrick, G. M. (1997). SHELXL97. University of Göttingen, Germany.
;
_publ_section_exptl_prep
;
Ether/methanol or ether/ethanol was used as the solvent for mixing and
recrystallization.
;
_publ_section_exptl_refinement
;
In (II), there is an orientational disorder of the C=C double bond of the
3'-nitro-cinnamate ion. The occupancy factors were 0.768(9) and 0.232(9)
for C8/C9 and C8*/C9*, respectively. The H atoms bonded to N11 and N12 of (I),
and N6 of (II) were located from difference syntheses and were refined
isotropically. The N---H bond distances are 0.83(2)--0.99(3)Å in (I) and
0.74(3)--0.95(3)Å in (II). The other H-atom positional parameters were
calculated geometrically and fixed with Uiso(H) = 1.2Ueq(parent atom).
;
data_I
_chemical_name_systematic
;
propane-1,3-diammonium bis[(E)-3-(3-nitrophenyl)propenoate]
;
_chemical_formula_moiety     'C3 H12 N2 2+, 2C9 H6 N1 O4 1-'
_chemical_formula_sum     'C21 H24 N4 O8 '
_chemical_formula_iupac     'C3 H12 N2 2+, 2C9 H6 N1 O4 1-'
_chemical_formula_weight     460.44
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c a'
_symmetry_space_group_name_Hall     '-P 2ac 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    x,y,z
    1/2+x,1/2-y,-z
    -x,1/2+y,1/2-z
    1/2-x,-y,1/2+z
    -x,-y,-z
    1/2-x,1/2+y,z
    x,1/2-y,1/2+z
    1/2+x,y,1/2-z
_cell_length_a     7.136(3)
_cell_length_b     23.710(3)
_cell_length_c     25.964(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     4393.0(18)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     12.3
_cell_measurement_theta_max     14.8
_cell_measurement_temperature     298.0(10)
_exptl_crystal_description     prism
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max      .7
_exptl_crystal_size_mid      .4
_exptl_crystal_size_min      .4
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.392
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_absorpt_coefficient_mu      .108
_exptl_absorpt_correction_type     none
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_measurement_device_type     'Rigaku AFC-7R'
_diffrn_measurement_method     ω
_diffrn_reflns_number     5308
_diffrn_reflns_av_R_equivalents      .011
_diffrn_reflns_theta_min     2.5
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     31
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     34
_diffrn_standards_number     3
_diffrn_standards_interval_count     150
_diffrn_standards_decay_%     1.5
_refine_special_details
;
Refinement was based on F² against all reflections. The weighted R-factor
(wR) and goodness of fit (S) were based on F², and conventional R-factor (R)
was calculated on F, with F set to zero for negative F². The threshold
expression of I > 2σ(I) was used only for calculating R-factor(gt).
;
_reflns_number_total     5040
_reflns_number_gt     3317
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_gt      .056
_refine_ls_wR_factor_ref      .167
_refine_ls_goodness_of_fit_ref     1.03
_refine_ls_number_reflns     5040
_refine_ls_number_parameters     322
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'w = 1/[σ²(Fo²) + (0.0829P)²+1.5750P] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max      .001
_refine_diff_density_max      .54
_refine_diff_density_min      -.27
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .003  .002
;International Tables for Crystallography
(1992, Vol. C)
;
    'H' 'H'  .000  .000
;International Tables for Crystallography
(1992, Vol. C)
;
    'N' 'N'  .006  .003
;International Tables for Crystallography
(1992, Vol. C)
;
    'O' 'O'  .011  .006
;International Tables for Crystallography
(1992, Vol. C)
;
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993)
;
_computing_cell_refinement     'MSC/AFC Diffractometer Control Software'
_computing_data_reduction     'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement     'TEXSAN'
_computing_molecular_graphics     ?
_computing_publication_material     'TEXSAN'
loop_
    _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
    _atom_site_type_symbol
    O1  .7685(3)  .60955(6)  .10519(5)  .0584(5) Uani d . 1.00 . . O
    O2  .8838(3)  .54097(6)  .05626(6)  .0560(4) Uani d . 1.00 . . O
    O3  .7878(4)  .57420(10)
                            .37654(8)  .0943(7) Uani d . 1.00 . . O
    O4  .8114(4)  .49550(10)
                            .41604(7)  .1070(9) Uani d . 1.00 . . O
    O5  .5076(2)  .35244(6)  .40834(6)  .0568(4) Uani d . 1.00 . . O
    O6  .4939(2)  .27819(6)  .46020(5)  .0519(4) Uani d . 1.00 . . O
    O7  .5328(3)  .32718(9)  .13686(7)  .0796(6) Uani d . 1.00 . . O
    O8  .5148(4)  .24960(10)
                            .09443(6)  .0921(7) Uani d . 1.00 . . O
    N9  .7978(3)  .52340(10)
                            .37682(8)  .0682(6) Uani d . 1.00 . . N
    N10  .5161(3)  .27630(10)
                             .13454(7)  .0590(5) Uani d . 1.00 . . N
    N11  .8656(3)  .42929(8)  .02374(8)  .0445(4) Uani d . 1.00 . . N
    N12  .2876(3)  .32104(8)  -.02145(7)  .0394(4) Uani d . 1.00 . . N
    C13  .8198(3)  .56004(8)  .09756(8)  .0432(5) Uani d . 1.00 . . C
    C14  .8109(3)  .51834(8)  .14136(8)  .0488(5) Uani d . 1.00 . . C
    C15  .7773(3)  .53429(8)  .18830(8)  .0471(5) Uani d . 1.00 . . C
    C16  .7762(3)  .49815(9)  .23542(8)  .0436(5) Uani d . 1.00 . . C
    C17  .7908(3)  .52460(8)  .28273(8)  .0464(5) Uani d . 1.00 . . C
    C18  .7856(3)  .49280(10)
                             .32723(8)  .0468(5) Uani d . 1.00 . . C
    C19  .7660(3)  .43550(10)
                             .32726(8)  .0529(6) Uani d . 1.00 . . C
    C20  .7530(3)  .40880(9)  .28000(10)
                                        .0556(6) Uani d . 1.00 . . C
    C21  .7576(3)  .43970(10)
                             .23429(8)  .0499(5) Uani d . 1.00 . . C
    C22  .4985(3)  .30082(9)  .41634(8)  .0418(4) Uani d . 1.00 . . C
    C23  .4953(3)  .26128(8)  .37088(8)  .0468(5) Uani d . 1.00 . . C
    C24  .4851(3)  .27994(8)  .32347(7)  .0425(5) Uani d . 1.00 . . C
    C25  .4830(3)  .24642(9)  .27551(7)  .0391(4) Uani d . 1.00 . . C
    C26  .5000(3)  .27481(8)  .22891(8)  .0430(5) Uani d . 1.00 . . C
    C27  .4971(3)  .24429(9)  .18313(7)  .0445(5) Uani d . 1.00 . . C
    C28  .4789(3)  .18680(10)
                             .18207(8)  .0515(5) Uani d . 1.00 . . C
    C29  .4626(4)  .15882(9)  .22832(9)  .0550(6) Uani d . 1.00 . . C
    C30  .4642(3)  .18779(9)  .27492(8)  .0470(5) Uani d . 1.00 . . C
    C31  .6597(3)  .42152(8)  .02746(8)  .0480(5) Uani d . 1.00 . . C
    C32  .5874(3)  .37048(8)  -.00108(7)  .0435(5) Uani d . 1.00 . . C
    C33  .3837(3)  .36166(8)  .01305(7)  .0421(5) Uani d . 1.00 . . C
    H11A  .895(4)  .4610(10)
                            .0390(9)  .05732(9) Uiso d . 1.00 . . H
    H11B  .935(4)  .4000(10)
                            .0430(10)
                                     .06619(10) Uiso d . 1.00 . . H
    H11C  .905(3)  .4284(9)  -.0068(10)  .04702(8) Uiso d . 1.00 . . H
    H12A  .180(4)  .3093(9)  -.0068(9)  .05057(8) Uiso d . 1.00 . . H
    H12B  .355(3)  .2940(10)
                            -.0273(9)  .05095(9) Uiso d . 1.00 . . H
    H12C  .258(3)  .3390(10)
                            -.0544(10)  .06132(9) Uiso d . 1.00 . . H
    H14  .8357  .4787  .1353  .0533 Uiso calc . 1.00 . . H
    H15  .7497  .5738  .1948  .0495 Uiso calc . 1.00 . . H
    H17  .8047  .5651  .2843  .0477 Uiso calc . 1.00 . . H
    H19  .7593  .4132  .3574  .0575 Uiso calc . 1.00 . . H
    H20  .7427  .3683  .2770  .0572 Uiso calc . 1.00 . . H
    H21  .7469  .4207  .2017  .0526 Uiso calc . 1.00 . . H
    H23  .5012  .2215  .3769  .0481 Uiso calc . 1.00 . . H
    H24  .4796  .3201  .3183  .0433 Uiso calc . 1.00 . . H
    H26  .5142  .3154  .2285  .0432 Uiso calc . 1.00 . . H
    H28  .4782  .1656  .1514  .0559 Uiso calc . 1.00 . . H
    H29  .4453  .1183  .2290  .0584 Uiso calc . 1.00 . . H
    H30  .4575  .1668  .3068  .0495 Uiso calc . 1.00 . . H
    H31A  .6272  .4179  .0632  .0490 Uiso calc . 1.00 . . H
    H31B  .5994  .4546  .0135  .0490 Uiso calc . 1.00 . . H
    H32A  .6594  .3377  .0087  .0446 Uiso calc . 1.00 . . H
    H32B  .5997  .3761  -.0377  .0446 Uiso calc . 1.00 . . H
    H33A  .3185  .3975  .0105  .0431 Uiso calc . 1.00 . . H
    H33B  .3748  .3483  .0478  .0431 Uiso calc . 1.00 . . H
_geom_special_details
;
 ?
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C13 . . 1.245(2) yes
    O2 C13 . . 1.250(3) yes
    O3 N9 . . 1.205(4) yes
    O4 N9 . . 1.219(3) yes
    O5 C22 . . 1.243(3) yes
    O6 C22 . . 1.259(3) yes
    O7 N10 . . 1.213(3) yes
    O8 N10 . . 1.219(3) yes
    N9 C18 . . 1.481(3) no
    N10 C27 . . 1.479(3) no
    N11 C31 . . 1.484(3) yes
    N11 H11A . .  .87(3) no
    N11 H11B . .  .99(3) no
    N11 H11C . .  .84(3) no
    N12 C33 . . 1.483(3) yes
    N12 H12A . .  .90(2) no
    N12 H12B . .  .83(2) no
    N12 H12C . .  .98(2) no
    C13 C14 . . 1.508(3) no
    C14 C15 . . 1.298(3) no
    C14 H14 . .  .97 no
    C15 C16 . . 1.494(3) no
    C15 H15 . .  .97 no
    C16 C17 . . 1.383(3) no
    C16 C21 . . 1.392(3) no
    C17 C18 . . 1.380(3) no
    C17 H17 . .  .97 no
    C18 C19 . . 1.367(3) no
    C19 C20 . . 1.383(3) no
    C19 H19 . .  .95 no
    C20 C21 . . 1.396(3) no
    C20 H20 . .  .97 no
    C21 H21 . .  .96 no
    C22 C23 . . 1.508(3) no
    C23 C24 . . 1.310(3) no
    C23 H23 . .  .96 no
    C24 C25 . . 1.477(3) no
    C24 H24 . .  .96 no
    C25 C26 . . 1.390(3) no
    C25 C30 . . 1.397(3) no
    C26 C27 . . 1.392(3) no
    C26 H26 . .  .97 no
    C27 C28 . . 1.369(3) no
    C28 C29 . . 1.377(3) no
    C28 H28 . .  .94 no
    C29 C30 . . 1.391(3) no
    C29 H29 . .  .97 no
    C30 H30 . .  .97 no
    C31 C32 . . 1.510(3) no
    C31 H31A . .  .96 no
    C31 H31B . .  .97 no
    C32 C33 . . 1.514(3) no
    C32 H32A . .  .97 no
    C32 H32B . .  .96 no
    C33 H33A . .  .97 no
    C33 H33B . .  .96 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O3 N9 O4 . . . 123.6(2) yes
    O3 N9 C18 . . . 118.8(2) no
    O4 N9 C18 . . . 117.6(3) no
    O7 N10 O8 . . . 124.1(2) yes
    O7 N10 C27 . . . 118.5(2) no
    O8 N10 C27 . . . 117.4(2) no
    C31 N11 H11A . . . 109(2) no
    C31 N11 H11B . . . 112(2) no
    C31 N11 H11C . . . 113(2) no
    H11A N11 H11B . . . 104(2) no
    H11A N11 H11C . . . 112(2) no
    H11B N11 H11C . . . 108(2) no
    C33 N12 H12A . . . 110.0(10)
                              no
    C33 N12 H12B . . . 111(2) no
    C33 N12 H12C . . . 110.0(10)
                              no
    H12A N12 H12B . . . 109(2) no
    H12A N12 H12C . . . 109(2) no
    H12B N12 H12C . . . 108(2) no
    O1 C13 O2 . . . 125.8(2) yes
    O1 C13 C14 . . . 119.0(2) no
    O2 C13 C14 . . . 115.2(2) no
    C13 C14 C15 . . . 121.6(2) no
    C13 C14 H14 . . . 120 no
    C15 C14 H14 . . . 118 no
    C14 C15 C16 . . . 127.1(2) no
    C14 C15 H15 . . . 119 no
    C16 C15 H15 . . . 114 no
    C15 C16 C17 . . . 117.8(2) no
    C15 C16 C21 . . . 123.7(2) no
    C17 C16 C21 . . . 118.5(2) no
    C16 C17 C18 . . . 119.6(2) no
    C16 C17 H17 . . . 120 no
    C18 C17 H17 . . . 121 no
    N9 C18 C17 . . . 117.3(2) no
    N9 C18 C19 . . . 119.6(2) no
    C17 C18 C19 . . . 123.1(2) no
    C18 C19 C20 . . . 117.4(2) no
    C18 C19 H19 . . . 124 no
    C20 C19 H19 . . . 118 no
    C19 C20 C21 . . . 120.8(2) no
    C19 C20 H20 . . . 122 no
    C21 C20 H20 . . . 117 no
    C16 C21 C20 . . . 120.5(2) no
    C16 C21 H21 . . . 120 no
    C20 C21 H21 . . . 120 no
    O5 C22 O6 . . . 124.9(2) yes
    O5 C22 C23 . . . 118.8(2) no
    O6 C22 C23 . . . 116.3(2) no
    C22 C23 C24 . . . 121.8(2) no
    C22 C23 H23 . . . 119 no
    C24 C23 H23 . . . 119 no
    C23 C24 C25 . . . 127.7(2) no
    C23 C24 H24 . . . 118 no
    C25 C24 H24 . . . 114 no
    C24 C25 C26 . . . 118.2(2) no
    C24 C25 C30 . . . 123.1(2) no
    C26 C25 C30 . . . 118.7(2) no
    C25 C26 C27 . . . 119.4(2) no
    C25 C26 H26 . . . 120 no
    C27 C26 H26 . . . 121 no
    N10 C27 C26 . . . 117.4(2) no
    N10 C27 C28 . . . 120.2(2) no
    C26 C27 C28 . . . 122.4(2) no
    C27 C28 C29 . . . 118.1(2) no
    C27 C28 H28 . . . 123 no
    C29 C28 H28 . . . 119 no
    C28 C29 C30 . . . 121.3(2) no
    C28 C29 H29 . . . 120 no
    C30 C29 H29 . . . 118 no
    C25 C30 C29 . . . 120.1(2) no
    C25 C30 H30 . . . 121 no
    C29 C30 H30 . . . 119 no
    N11 C31 C32 . . . 113.9(2) no
    N11 C31 H31A . . . 108 no
    N11 C31 H31B . . . 108 no
    C32 C31 H31A . . . 109 no
    C32 C31 H31B . . . 108 no
    H31A C31 H31B . . . 109 no
    C31 C32 C33 . . . 108.7(2) no
    C31 C32 H32A . . . 110 no
    C31 C32 H32B . . . 110 no
    C33 C32 H32A . . . 110 no
    C33 C32 H32B . . . 110 no
    H32A C32 H32B . . . 109 no
    N12 C33 C32 . . . 112.8(2) no
    N12 C33 H33A . . . 108 no
    N12 C33 H33B . . . 109 no
    C32 C33 H33A . . . 109 no
    C32 C33 H33B . . . 110 no
    H33A C33 H33B . . . 109 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
    N11 H11A O2 .  .87(3) 1.96(3) 2.782(2) 158(2)
    N11 H11B O5 8_555  .99(3) 1.77(3) 2.731(3) 164(2)
    N11 H11C O2 5_765  .84(3) 2.11(2) 2.830(3) 144(2)
    N12 H12A O6 8_455  .90(2) 1.94(2) 2.820(3) 164(2)
    N12 H12B O6 7_554  .83(2) 1.99(2) 2.816(2) 174(2)
    N12 H12C O1 5_665  .98(2) 1.80(2) 2.756(2) 163(2)
data_II
_chemical_name_systematic
;
trans-cyclohexane-1,2-diammonium bis[(E)-3-(3-nitrophenyl)propenoate]
;
_chemical_formula_moiety     'C6 H16 N2 2+, 2C9 H6 N1 O4 1-'
_chemical_formula_sum     'C24 H28 N4 O8 '
_chemical_formula_iupac     'C6 H16 N2 2+, 2C9 H6 N1 O4 1-'
_chemical_formula_weight     500.51
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P b c n'
_symmetry_space_group_name_Hall     '-P 2n 2ab'
loop_
    _symmetry_equiv_pos_as_xyz
    x,y,z
    1/2-x,1/2-y,1/2+z
    1/2+x,1/2-y,-z
    -x,y,1/2-z
    -x,-y,-z
    1/2+x,1/2+y,1/2-z
    1/2-x,1/2+y,z
    x,-y,1/2+z
_cell_length_a     26.919(4)
_cell_length_b     7.572(3)
_cell_length_c     11.966(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2439.1(10)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     12.2
_cell_measurement_theta_max     14.6
_cell_measurement_temperature     298.0(10)
_exptl_crystal_description     prism
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max      .7
_exptl_crystal_size_mid      .3
_exptl_crystal_size_min      .3
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.363
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_absorpt_coefficient_mu      .103
_exptl_absorpt_correction_type     none
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength      .71073
_diffrn_measurement_device_type     'Rigaku AFC-7R'
_diffrn_measurement_method     ω
_diffrn_reflns_number     2942
_diffrn_reflns_av_R_equivalents      .018
_diffrn_reflns_theta_min     2.5
_diffrn_reflns_theta_max     27.5
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     35
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     3
_diffrn_reflns_limit_l_min     0
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     3
_diffrn_standards_interval_count     150
_diffrn_standards_decay_%      .7
_refine_special_details
;
Refinement was based on F² against all reflections. The weighted R-factor
(wR) and goodness of fit (S) were based on F², and conventional R-factor (R)
was calculated on F, with F set to zero for negative F². The threshold
expression of I > 2σ(I) was used only for calculating R-factor(gt).
;
_reflns_number_total     2798
_reflns_number_gt     1507
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_R_factor_gt      .074
_refine_ls_wR_factor_ref      .190
_refine_ls_goodness_of_fit_ref     1.77
_refine_ls_number_reflns     2798
_refine_ls_number_parameters     183
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                  'w = 1/[σ²(Fo²) + (0.05P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_shift/su_max      .001
_refine_diff_density_max      .44
_refine_diff_density_min      -.28
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C'  .003  .002
;International Tables for Crystallography
(1992, Vol. C)
;
    'H' 'H'  .000  .000
;International Tables for Crystallography
(1992, Vol. C)
;
    'N' 'N'  .006  .003
;International Tables for Crystallography
(1992, Vol. C)
;
    'O' 'O'  .011  .006
;International Tables for Crystallography
(1992, Vol. C)
;
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993)
;
_computing_cell_refinement     'MSC/AFC Diffractometer Control Software'
_computing_data_reduction     'TEXSAN (Molecular Structure Corporation, 1999)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement     'TEXSAN'
_computing_molecular_graphics     ?
_computing_publication_material     'TEXSAN'
loop_
    _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
    _atom_site_type_symbol
    O1  .10530(6)  .0501(4)  .2810(2)  .0859(8) Uani d . 1.000 . . O
    O2  .05685(6)  .1001(3)  .4259(2)  .0607(5) Uani d . 1.000 . . O
    O3  .36440(10)
                  .1033(6)  .3552(3)  .165(2) Uani d . 1.000 . . O
    O4  .40302(8)  .1785(4)  .5033(3)  .1210(10)
                                               Uani d . 1.000 . . O
    N5  .36570(10)
                  .1378(4)  .4536(3)  .0903(9) Uani d . 1.000 . . N
    N6  .02920(10)
                  .0621(3)  .6489(2)  .0472(6) Uani d . 1.000 . . N
    C7  .09833(9)  .0852(4)  .3803(3)  .0540(7) Uani d . 1.000 . . C
    C8  .13970(10)
                  .1127(5)  .4635(3)  .0550(10)
                                              Uani d P  .768(9) . A C
    C8*  .1564(5)  .100(2)  .4100(10)
                                     .05422(5) Uiso d P  .232(9) . B C
    C9  .18670(10)
                  .0853(5)  .4349(2)  .0530(10)
                                              Uani d P  .768(9) . A C
    C9*  .1695(5)  .118(2)  .5084(9)  .06496(6) Uiso d P  .232(9) . B C
    C10  .23050(10)
                   .1130(4)  .5083(3)  .0668(8) Uani d . 1.000 . . C
    C11  .27500(10)
                   .1120(4)  .4557(2)  .0724(9) Uani d . 1.000 . . C
    C12  .31802(9)  .1371(4)  .5157(3)  .0626(8) Uani d . 1.000 . . C
    C13  .31886(9)  .1628(4)  .6286(3)  .0677(9) Uani d . 1.000 . . C
    C14  .27310(10)
                   .1626(5)  .6848(2)  .0773(9) Uani d . 1.000 . . C
    C15  .22908(9)  .1375(4)  .6228(3)  .0747(9) Uani d . 1.000 . . C
    C16  .00690(10)
                   .2262(4)  .6912(2)  .0638(8) Uani d . 1.000 . . C
    C17  .03225(9)  .3881(4)  .6521(2)  .0620(7) Uani d . 1.000 . . C
    C18  .00920(10)
                   .5554(4)  .6927(3)  .0930(10)
                                               Uani d . 1.000 . . C
    H6A  .0530(10)
                  .004(5)  .694(3)  .10270(10)
                                             Uiso d . 1.000 . . H
    H6B  .0416(10)  .080(4)  .580(3)  .06420(10)
                                               Uiso d . 1.000 . . H
    H6C  .0093(10)  -.005(4)  .643(2)  .04900(10)
                                                Uiso d . 1.000 . . H
    H8  .1319  .1507  .5379  .0655 Uiso calc P  .768(9) . A H
    H8*  .1810  .0941  .3517  .0662 Uiso calc P  .232(9) . B H
    H9  .1930  .0438  .3604  .0637 Uiso calc P  .768(9) . A H
    H9*  .1481  .1326  .5721  .0773 Uiso calc P  .232(9) . B H
    H11  .2766  .0941  .3763  .0867 Uiso calc . 1.000 . . H
    H13  .3495  .1801  .6679  .0812 Uiso calc . 1.000 . . H
    H14  .2718  .1792  .7642  .0928 Uiso calc . 1.000 . . H
    H15  .1977  .1374  .6605  .0898 Uiso calc . 1.000 . . H
    H16  -.0251  .2307  .6534  .0760 Uiso calc . 1.000 . . H
    H17A  .0318  .3893  .5719  .0743 Uiso calc . 1.000 . . H
    H17B  .0659  .3838  .6780  .0743 Uiso calc . 1.000 . . H
    H18A  .0338  .6465  .6873  .1115 Uiso calc . 1.000 . . H
    H18B  -.0182  .5823  .6446  .1115 Uiso calc . 1.000 . . H
_geom_special_details
;
 ?
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C7 . . 1.233(4) yes
    O2 C7 . . 1.248(3) yes
    O3 N5 . . 1.207(6) yes
    O4 N5 . . 1.207(4) yes
    N5 C12 . . 1.484(4) no
    N6 C16 . . 1.470(4) yes
    N6 H6A . .  .95(3) no
    N6 H6B . .  .90(3) no
    N6 H6C . .  .74(3) no
    C7 C8 . . 1.508(4) no
    C7 C8* . . 1.608(13) no
    C8 C9 . . 1.329(5) no
    C8 H8 . .  .96 no
    C8* C9* . . 1.234(16) no
    C8* H8* . .  .97 no
    C9 C10 . . 1.484(5) no
    C9 H9 . .  .96 no
    C9* C10 . . 1.642(13) no
    C9* H9* . .  .96 no
    C10 C11 . . 1.354(4) no
    C10 C15 . . 1.382(5) no
    C11 C12 . . 1.376(4) no
    C11 H11 . .  .96 no
    C12 C13 . . 1.365(5) no
    C13 C14 . . 1.403(4) no
    C13 H13 . .  .96 no
    C14 C15 . . 1.412(4) no
    C14 H14 . .  .96 no
    C15 H15 . .  .96 no
    C16 C16 . 4_556 1.455(5) no
    C16 C17 . . 1.480(4) no
    C16 H16 . .  .97 no
    C17 C18 . . 1.492(4) no
    C17 H17A . .  .96 no
    C17 H17B . .  .96 no
    C18 C18 . 4_556 1.458(7) no
    C18 H18A . .  .96 no
    C18 H18B . .  .96 no
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O3 N5 O4 . . . 124.1(3) yes
    O3 N5 C12 . . . 117.6(3) no
    O4 N5 C12 . . . 118.2(3) no
    C16 N6 H6A . . . 118(2) no
    C16 N6 H6B . . . 110(2) no
    C16 N6 H6C . . . 109(2) no
    H6A N6 H6B . . . 110(3) no
    H6A N6 H6C . . . 104(3) no
    H6B N6 H6C . . . 106(3) no
    O1 C7 O2 . . . 125.3(2) yes
    O1 C7 C8 . . . 123.6(2) no
    O1 C7 C8* . . . 94.7(5) no
    O2 C7 C8 . . . 111.1(3) no
    O2 C7 C8* . . . 140.1(5) no
    C7 C8 C9 . . . 120.8(3) no
    C7 C8 H8 . . . 120 no
    C9 C8 H8 . . . 120 no
    C7 C8* C9* . . . 119.8(11) no
    C7 C8* H8* . . . 120 no
    C9* C8* H8* . . . 120 no
    C8 C9 C10 . . . 125.6(3) no
    C8 C9 H9 . . . 117 no
    C10 C9 H9 . . . 117 no
    C8* C9* C10 . . . 106.3(10) no
    C8* C9* H9* . . . 127 no
    C10 C9* H9* . . . 127 no
    C9 C10 C11 . . . 115.2(3) no
    C9 C10 C15 . . . 125.7(3) no
    C9* C10 C11 . . . 152.3(5) no
    C9* C10 C15 . . . 88.2(4) no
    C11 C10 C15 . . . 119.0(3) no
    C10 C11 C12 . . . 120.1(3) no
    C10 C11 H11 . . . 120 no
    C12 C11 H11 . . . 120 no
    N5 C12 C11 . . . 117.8(3) no
    N5 C12 C13 . . . 118.8(3) no
    C11 C12 C13 . . . 123.4(2) no
    C12 C13 C14 . . . 117.4(2) no
    C12 C13 H13 . . . 121 no
    C14 C13 H13 . . . 121 no
    C13 C14 C15 . . . 119.0(3) no
    C13 C14 H14 . . . 121 no
    C15 C14 H14 . . . 121 no
    C10 C15 C14 . . . 121.1(3) no
    C10 C15 H15 . . . 119 no
    C14 C15 H15 . . . 120 no
    N6 C16 C16 . . 4_556 115.9(2) no
    N6 C16 C17 . . . 113.7(2) no
    N6 C16 H16 . . . 103 no
    C16 C16 C17 4_556 . . 115.0(2) no
    C16 C16 H16 4_556 . . 103 no
    C17 C16 H16 . . . 103 no
    C16 C17 C18 . . . 114.1(2) no
    C16 C17 H17A . . . 109 no
    C16 C17 H17B . . . 108 no
    C18 C17 H17A . . . 108 no
    C18 C17 H17B . . . 109 no
    H17A C17 H17B . . . 110 no
    C17 C18 C18 . . 4_556 116.6(2) no
    C17 C18 H18A . . . 108 no
    C17 C18 H18B . . . 108 no
    C18 C18 H18A 4_556 . . 107 no
    C18 C18 H18B 4_556 . . 108 no
    H18A C18 H18B . . . 110 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
    N6 H6A O1 8_555  .95(3) 1.80(3) 2.723(3) 166(3)
    N6 H6B O2 .  .90(3) 1.89(3) 2.786(3) 170(2)
    N6 H6C O2 5_556  .74(3) 2.09(3) 2.771(3) 153(3)
