#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013281.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_2013281
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2003
_journal_volume  59
_journal_page_first  o286
_journal_page_last  o288
_publ_section_title
;
Hydrogen bonding in (S,S)-N,N'-bis[2-azido-1-(2-methylpropyl)ethyl]oxalamide;
digonal symmetry of R~2~^2^(10) hydrogen-bonded dimers connected into
an \a-network
;
_space_group_IT_number           5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_[local]_cod_cif_authors_sg_H-M  'C 2'
loop_
_publ_author_name
  "Zoran \<Stefani\'c"
  "Biserka Koji\'c-Prodi\'c"
  "Zoran D\<zoli\'c"
  "Darinka Kataleni\'c"
  "Mladen \<Zini\'c"
  'Anton Meden'
_chemical_formula_moiety  'C14 H26 N8 O2'
_chemical_formula_sum  'C14 H26 N8 O2'
_chemical_formula_iupac  'C14 H26 N8 O2'
_chemical_formula_weight  338.43
_symmetry_cell_setting  monoclinic
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'
_cell_length_a  24.0235(5)
_cell_length_b  7.9361(2)
_cell_length_c  20.2167(5)
_cell_angle_alpha  90
_cell_angle_beta  107.8240(10)
_cell_angle_gamma  90
_cell_volume  3669.37(15)
_cell_formula_units_Z  8
_cell_measurement_temperature  150.0(10)
_exptl_crystal_density_diffrn  1.225
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
  O13 0.94280(8) 0.4182(2) 0.91922(9) 0.0340(4) Uani d . 1 . . O
  O1 0.94218(7) 0.4575(2) 0.66378(8) 0.0289(4) Uani d . 1 . . O
  O12 1.03112(8) 0.5700(2) 0.82281(8) 0.0346(4) Uani d . 1 . . O
  N11 1.04680(9) 0.6132(3) 0.68753(10) 0.0242(5) Uani d . 1 . . N
  N1 0.93215(9) 0.4428(3) 0.54865(10) 0.0241(4) Uani d . 1 . . N
  O11 1.04798(7) 0.5308(2) 0.58041(8) 0.0315(4) Uani d . 1 . . O
  N12 1.05454(10) 0.5287(3) 0.93906(11) 0.0317(5) Uani d . 1 . . N
  N13 0.92591(9) 0.4302(3) 0.80212(11) 0.0281(5) Uani d . 1 . . N
  C2 0.87294(10) 0.3753(3) 0.52703(13) 0.0265(5) Uani d . 1 . . C
  H2 0.8571 0.3854 0.5662 0.032 Uiso calc R 1 . . H
  C1 0.96135(10) 0.4757(3) 0.61449(12) 0.0224(5) Uani d . 1 . . C
  C13 0.95800(11) 0.4499(3) 0.86784(12) 0.0265(5) Uani d . 1 . . C
  N21 1.20955(10) 0.6180(3) 0.77775(13) 0.0373(5) Uani d . 1 . . N
  C11 1.02356(10) 0.5428(3) 0.62557(12) 0.0225(5) Uani d . 1 . . C
  C4 0.83261(11) 0.4716(4) 0.46543(13) 0.0295(6) Uani d . 1 . . C
  H4A 0.7934 0.4264 0.4556 0.035 Uiso calc R 1 . . H
  H4B 0.8453 0.4505 0.425 0.035 Uiso calc R 1 . . H
  C23 0.86768(11) 0.3572(3) 0.77892(13) 0.0293(6) Uani d . 1 . . C
  H23 0.8552 0.3298 0.8195 0.035 Uiso calc R 1 . . H
  C12 1.01901(11) 0.5224(3) 0.87473(12) 0.0275(6) Uani d . 1 . . C
  N23 0.91222(13) 0.0748(4) 0.78074(13) 0.0496(7) Uani d . 1 . . N
  C41 1.10451(12) 0.8488(3) 0.75174(13) 0.0276(5) Uani d . 1 . . C
  H41A 1.0904 0.8217 0.7906 0.033 Uiso calc R 1 . . H
  H41B 1.1444 0.8886 0.7707 0.033 Uiso calc R 1 . . H
  C51 1.06744(12) 0.9915(3) 0.71073(13) 0.0312(6) Uani d . 1 . . C
  H51 1.0277 0.9484 0.6898 0.037 Uiso calc R 1 . . H
  C53 0.81026(12) 0.6387(4) 0.76647(14) 0.0345(6) Uani d . 1 . . C
  H53 0.8473 0.6881 0.7948 0.041 Uiso calc R 1 . . H
  C21 1.10508(11) 0.6874(3) 0.71088(13) 0.0274(6) Uani d . 1 . . C
  H21 1.117 0.7156 0.67 0.033 Uiso calc R 1 . . H
  C31 1.14696(11) 0.5542(3) 0.75314(13) 0.0321(6) Uani d . 1 . . C
  H31A 1.1349 0.5228 0.7931 0.039 Uiso calc R 1 . . H
  H31B 1.145 0.4544 0.7248 0.039 Uiso calc R 1 . . H
  C6 0.81837(12) 0.7088(4) 0.54283(14) 0.0382(7) Uani d . 1 . . C
  H6A 0.8171 0.8291 0.5468 0.057 Uiso calc R 1 . . H
  H6B 0.8491 0.6644 0.5813 0.057 Uiso calc R 1 . . H
  H6C 0.7816 0.6618 0.5431 0.057 Uiso calc R 1 . . H
  C33 0.86818(12) 0.1972(3) 0.73754(14) 0.0346(6) Uani d . 1 . . C
  H33A 0.8296 0.1462 0.7239 0.042 Uiso calc R 1 . . H
  H33B 0.878 0.2247 0.6957 0.042 Uiso calc R 1 . . H
  N33 0.92140(11) -0.0423(4) 0.75094(15) 0.0459(6) Uani d . 1 . . N
  C43 0.82392(11) 0.4803(3) 0.73210(13) 0.0316(6) Uani d . 1 . . C
  H43A 0.8389 0.5142 0.6946 0.038 Uiso calc R 1 . . H
  H43B 0.7876 0.4204 0.7113 0.038 Uiso calc R 1 . . H
  C22 1.11408(12) 0.5955(4) 0.95643(13) 0.0356(6) Uani d . 1 . . C
  H22 1.1188 0.6481 0.9146 0.043 Uiso calc R 1 . . H
  C5 0.82999(11) 0.6628(3) 0.47530(13) 0.0319(6) Uani d . 1 . . C
  H5 0.868 0.7103 0.4766 0.038 Uiso calc R 1 . . H
  N22 1.15505(14) 0.3468(4) 0.91575(13) 0.0531(7) Uani d . 1 . . N
  N32 1.17922(12) 0.2187(5) 0.92676(14) 0.0578(8) Uani d . 1 . . N
  N2 0.90824(14) 0.0881(3) 0.57360(13) 0.0473(7) Uani d . 1 . . N
  C3 0.87373(13) 0.1891(4) 0.50872(14) 0.0370(6) Uani d . 1 . . C
  H3A 0.8919 0.1751 0.4723 0.044 Uiso calc R 1 . . H
  H3B 0.834 0.1469 0.4917 0.044 Uiso calc R 1 . . H
  C71 1.08958(15) 1.0554(4) 0.65219(16) 0.0480(8) Uani d . 1 . . C
  H71A 1.0647 1.1448 0.6279 0.072 Uiso calc R 1 . . H
  H71B 1.0891 0.9649 0.6205 0.072 Uiso calc R 1 . . H
  H71C 1.1288 1.0967 0.6713 0.072 Uiso calc R 1 . . H
  C63 0.77265(14) 0.6005(5) 0.81405(16) 0.0487(8) Uani d . 1 . . C
  H63A 0.7648 0.7034 0.8345 0.073 Uiso calc R 1 . . H
  H63B 0.7933 0.5242 0.8501 0.073 Uiso calc R 1 . . H
  H63C 0.7364 0.5502 0.7872 0.073 Uiso calc R 1 . . H
  N43 0.93402(14) -0.1639(4) 0.72698(19) 0.0658(9) Uani d . 1 . . N
  N31 1.22629(11) 0.6502(4) 0.83772(17) 0.0518(7) Uani d . 1 . . N
  C42 1.12641(14) 0.7288(4) 1.01360(15) 0.0440(7) Uani d . 1 . . C
  H42A 1.1313 0.6717 1.0574 0.053 Uiso calc R 1 . . H
  H42B 1.1634 0.7822 1.0164 0.053 Uiso calc R 1 . . H
  C61 1.06429(15) 1.1373(4) 0.75922(16) 0.0461(8) Uani d . 1 . . C
  H61A 1.0407 1.2262 0.7326 0.069 Uiso calc R 1 . . H
  H61B 1.103 1.1788 0.7818 0.069 Uiso calc R 1 . . H
  H61C 1.0472 1.098 0.7935 0.069 Uiso calc R 1 . . H
  C32 1.15806(13) 0.4541(4) 0.97808(15) 0.0449(7) Uani d . 1 . . C
  H32A 1.1971 0.5003 0.9971 0.054 Uiso calc R 1 . . H
  H32B 1.1495 0.3862 1.0137 0.054 Uiso calc R 1 . . H
  C73 0.77896(14) 0.7676(4) 0.71150(17) 0.0453(8) Uani d . 1 . . C
  H73A 0.7705 0.8668 0.7339 0.068 Uiso calc R 1 . . H
  H73B 0.7431 0.72 0.6823 0.068 Uiso calc R 1 . . H
  H73C 0.8036 0.7969 0.6837 0.068 Uiso calc R 1 . . H
  C52 1.08105(17) 0.8664(4) 1.00621(17) 0.0548(9) Uani d . 1 . . C
  H52 1.0468 0.8157 1.015 0.066 Uiso calc R 1 . . H
  N42 1.20105(16) 0.0862(5) 0.93030(18) 0.0794(11) Uani d . 1 . . N
  N4 0.96361(18) -0.1333(5) 0.55828(19) 0.0867(12) Uani d . 1 . . N
  C7 0.78316(13) 0.7401(4) 0.41299(16) 0.0475(8) Uani d . 1 . . C
  H7A 0.7815 0.8597 0.4194 0.071 Uiso calc R 1 . . H
  H7B 0.7458 0.6913 0.4094 0.071 Uiso calc R 1 . . H
  H7C 0.7929 0.7177 0.3712 0.071 Uiso calc R 1 . . H
  C62 1.06080(19) 0.9483(5) 0.93493(19) 0.0680(11) Uani d . 1 . . C
  H62A 1.0321 1.033 0.9343 0.102 Uiso calc R 1 . . H
  H62B 1.0439 0.8643 0.9005 0.102 Uiso calc R 1 . . H
  H62C 1.0936 0.9992 0.925 0.102 Uiso calc R 1 . . H
  C72 1.1056(3) 1.0000(6) 1.0624(2) 0.0927(15) Uani d . 1 . . C
  H72A 1.0771 1.0873 1.0583 0.139 Uiso calc R 1 . . H
  H72B 1.1405 1.0475 1.0566 0.139 Uiso calc R 1 . . H
  H72C 1.1145 0.9487 1.1074 0.139 Uiso calc R 1 . . H
  N3 0.93357(14) -0.0144(5) 0.56273(15) 0.0600(8) Uani d . 1 . . N
  N41 1.24793(15) 0.6881(5) 0.89497(18) 0.0839(11) Uani d . 1 . . N
  H11N 1.0281(11) 0.602(3) 0.7161(13) 0.022(7) Uiso d . 1 . . H
  H1N 0.9496(12) 0.459(4) 0.5192(14) 0.028(7) Uiso d . 1 . . H
  H13N 0.9407(11) 0.456(3) 0.7725(13) 0.019(6) Uiso d . 1 . . H
  H12N 1.0426(11) 0.494(3) 0.9707(14) 0.024(7) Uiso d . 1 . . H
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
  O13 0.0394(11) 0.0418(11) 0.0225(9) -0.0107(9) 0.0118(8) -0.0018(8)
  O1 0.0320(10) 0.0361(10) 0.0200(8) -0.0061(8) 0.0100(7) -0.0021(8)
  O12 0.0367(10) 0.0467(11) 0.0199(9) -0.0118(9) 0.0079(7) 0.0022(8)
  N11 0.0258(11) 0.0297(12) 0.0191(10) -0.0048(9) 0.0097(9) -0.0034(9)
  N1 0.0235(11) 0.0307(12) 0.0187(10) -0.0019(9) 0.0073(9) 0.0004(9)
  O11 0.0273(9) 0.0453(11) 0.0229(9) -0.0045(8) 0.0092(7) -0.0085(8)
  N12 0.0342(13) 0.0410(14) 0.0196(11) -0.0125(10) 0.0076(9) 0.0004(10)
  N13 0.0286(12) 0.0372(13) 0.0190(11) -0.0074(10) 0.0081(9) 0.0017(9)
  C2 0.0239(13) 0.0321(14) 0.0236(12) -0.0040(11) 0.0073(10) -0.0007(11)
  C1 0.0265(13) 0.0199(12) 0.0211(12) 0.0004(10) 0.0078(10) -0.0008(10)
  C13 0.0328(14) 0.0260(13) 0.0216(12) -0.0023(11) 0.0096(10) 0.0002(10)
  N21 0.0296(12) 0.0419(14) 0.0408(14) 0.0046(11) 0.0114(11) -0.0046(11)
  C11 0.0245(12) 0.0224(12) 0.0197(12) 0.0029(10) 0.0053(9) 0.0021(10)
  C4 0.0233(13) 0.0412(15) 0.0229(12) -0.0032(12) 0.0056(10) -0.0024(11)
  C23 0.0312(14) 0.0351(15) 0.0218(12) -0.0074(12) 0.0081(11) 0.0005(11)
  C12 0.0364(15) 0.0246(13) 0.0214(13) -0.0038(11) 0.0086(11) -0.0018(10)
  N23 0.0645(18) 0.0473(17) 0.0329(14) 0.0023(15) 0.0090(12) 0.0051(13)
  C41 0.0321(14) 0.0267(13) 0.0232(12) -0.0068(11) 0.0074(10) -0.0006(10)
  C51 0.0323(14) 0.0301(14) 0.0305(14) -0.0008(12) 0.0085(11) 0.0030(11)
  C53 0.0329(14) 0.0402(16) 0.0329(14) -0.0077(13) 0.0136(12) -0.0089(12)
  C21 0.0272(13) 0.0305(14) 0.0240(12) -0.0051(11) 0.0070(10) -0.0009(11)
  C31 0.0318(14) 0.0314(14) 0.0308(14) -0.0010(12) 0.0059(11) -0.0044(12)
  C6 0.0358(15) 0.0397(16) 0.0386(16) 0.0070(13) 0.0108(12) -0.0021(13)
  C33 0.0365(15) 0.0323(15) 0.0313(14) -0.0062(13) 0.0049(12) -0.0001(12)
  N33 0.0388(15) 0.0407(17) 0.0637(18) 0.0060(13) 0.0237(13) 0.0199(15)
  C43 0.0288(14) 0.0378(15) 0.0264(13) -0.0067(12) 0.0059(11) -0.0032(12)
  C22 0.0355(15) 0.0447(17) 0.0238(13) -0.0106(13) 0.0046(11) -0.0016(12)
  C5 0.0263(14) 0.0371(15) 0.0305(14) 0.0024(12) 0.0061(11) 0.0065(11)
  N22 0.071(2) 0.0502(17) 0.0302(14) 0.0069(16) 0.0035(13) 0.0018(13)
  N32 0.0382(16) 0.096(3) 0.0390(16) 0.0067(18) 0.0122(12) -0.0010(17)
  N2 0.078(2) 0.0301(15) 0.0348(14) -0.0128(15) 0.0192(14) -0.0107(11)
  C3 0.0430(16) 0.0312(15) 0.0330(15) -0.0052(13) 0.0060(13) -0.0034(12)
  C71 0.059(2) 0.0445(18) 0.0446(17) 0.0056(16) 0.0218(15) 0.0182(15)
  C63 0.0443(18) 0.061(2) 0.0463(18) -0.0041(16) 0.0214(14) -0.0073(16)
  N43 0.059(2) 0.0431(17) 0.102(3) 0.0081(15) 0.0354(19) 0.0031(17)
  N31 0.0378(15) 0.0484(17) 0.060(2) -0.0007(13) 0.0009(14) 0.0048(14)
  C42 0.0489(18) 0.0517(19) 0.0292(15) -0.0180(16) 0.0086(13) -0.0062(13)
  C61 0.064(2) 0.0293(15) 0.0443(17) 0.0047(15) 0.0149(16) 0.0013(13)
  C32 0.0380(16) 0.058(2) 0.0332(15) -0.0017(16) 0.0036(12) -0.0008(15)
  C73 0.0458(18) 0.0385(17) 0.054(2) 0.0056(14) 0.0181(15) 0.0002(14)
  C52 0.074(2) 0.048(2) 0.0439(19) -0.0026(19) 0.0201(17) -0.0032(16)
  N42 0.071(2) 0.101(3) 0.069(2) 0.040(2) 0.0269(18) 0.008(2)
  N4 0.089(3) 0.068(2) 0.081(3) 0.025(2) -0.008(2) -0.010(2)
  C7 0.0405(17) 0.058(2) 0.0385(17) 0.0130(16) 0.0034(13) 0.0098(15)
  C62 0.091(3) 0.047(2) 0.063(2) 0.000(2) 0.018(2) 0.0016(19)
  C72 0.147(5) 0.066(3) 0.061(3) 0.004(3) 0.025(3) -0.019(2)
  N3 0.0560(19) 0.057(2) 0.0481(17) -0.0150(18) -0.0115(14) 0.0091(16)
  N41 0.076(2) 0.098(3) 0.055(2) -0.028(2) -0.0134(17) -0.009(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
  O13 C13 . 1.228(3) no
  O1 C1 . 1.227(3) no
  O12 C12 . 1.231(3) no
  N11 C11 . 1.328(3) no
  N11 C21 . 1.458(3) no
  N11 H11N . 0.84(3) no
  N1 C1 . 1.327(3) no
  N1 C2 . 1.456(3) no
  N1 H1N . 0.84(3) no
  O11 C11 . 1.231(3) no
  N12 C12 . 1.320(3) no
  N12 C22 . 1.464(3) no
  N12 H12N . 0.82(3) no
  N13 C13 . 1.325(3) no
  N13 C23 . 1.453(3) no
  N13 H13N . 0.81(3) no
  C2 C3 . 1.525(4) no
  C2 C4 . 1.528(3) no
  C2 H2 . 0.98 no
  C1 C11 . 1.537(3) no
  C13 C12 . 1.541(4) no
  N21 N31 . 1.183(4) no
  N21 C31 . 1.519(4) no
  C4 C5 . 1.534(4) no
  C4 H4A . 0.97 no
  C4 H4B . 0.97 no
  C23 C33 . 1.523(4) no
  C23 C43 . 1.532(4) no
  C23 H23 . 0.98 no
  N23 N33 . 1.165(4) no
  N23 C33 . 1.503(4) no
  C41 C51 . 1.520(4) no
  C41 C21 . 1.527(4) no
  C41 H41A . 0.97 no
  C41 H41B . 0.97 no
  C51 C71 . 1.525(4) no
  C51 C61 . 1.533(4) no
  C51 H51 . 0.98 no
  C53 C43 . 1.520(4) no
  C53 C73 . 1.528(4) no
  C53 C63 . 1.538(4) no
  C53 H53 . 0.98 no
  C21 C31 . 1.527(4) no
  C21 H21 . 0.98 no
  C31 H31A . 0.97 no
  C31 H31B . 0.97 no
  C6 C5 . 1.519(4) no
  C6 H6A . 0.96 no
  C6 H6B . 0.96 no
  C6 H6C . 0.96 no
  C33 H33A . 0.97 no
  C33 H33B . 0.97 no
  N33 N43 . 1.161(4) no
  C43 H43A . 0.97 no
  C43 H43B . 0.97 no
  C22 C32 . 1.511(4) no
  C22 C42 . 1.528(4) no
  C22 H22 . 0.98 no
  C5 C7 . 1.537(4) no
  C5 H5 . 0.98 no
  N22 N32 . 1.158(4) no
  N22 C32 . 1.504(4) no
  N32 N42 . 1.168(5) no
  N2 N3 . 1.078(4) no
  N2 C3 . 1.544(4) no
  C3 H3A . 0.97 no
  C3 H3B . 0.97 no
  C71 H71A . 0.96 no
  C71 H71B . 0.96 no
  C71 H71C . 0.96 no
  C63 H63A . 0.96 no
  C63 H63B . 0.96 no
  C63 H63C . 0.96 no
  N31 N41 . 1.154(4) no
  C42 C52 . 1.517(5) no
  C42 H42A . 0.97 no
  C42 H42B . 0.97 no
  C61 H61A . 0.96 no
  C61 H61B . 0.96 no
  C61 H61C . 0.96 no
  C32 H32A . 0.97 no
  C32 H32B . 0.97 no
  C73 H73A . 0.96 no
  C73 H73B . 0.96 no
  C73 H73C . 0.96 no
  C52 C62 . 1.519(5) no
  C52 C72 . 1.533(5) no
  C52 H52 . 0.98 no
  N4 N3 . 1.208(5) no
  C7 H7A . 0.96 no
  C7 H7B . 0.96 no
  C7 H7C . 0.96 no
  C62 H62A . 0.96 no
  C62 H62B . 0.96 no
  C62 H62C . 0.96 no
  C72 H72A . 0.96 no
  C72 H72B . 0.96 no
  C72 H72C . 0.96 no
_cod_database_code 2013281