data_2008947
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1547
_journal_page_last  1555
_publ_section_title
;
Molecular aggregation in selected crystalline 1:1 complexes of hydrophobic
D- and L-amino acids. III. The L-leucine and L-valine series.
;
loop_
_publ_author_name
  'Dalhus, Bj\/orn'
  'G\"orbitz, Carl Henrik'
_chemical_formula_moiety  'C5 H11 N O2 . C5 H11 N O2'
_chemical_formula_sum  'C10 H22 N2 O4 '
_chemical_formula_structural  'C5 H11 N O2 . C5 H11 N O2'
_chemical_formula_weight  234.30
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2'
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  27.2288(2)
_cell_length_b  4.73970(10)
_cell_length_c  9.95350(10)
_cell_angle_alpha  90.00
_cell_angle_beta  96.0910(10)
_cell_angle_gamma  90.00
_cell_volume  1277.31(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.218
_diffrn_ambient_temperature  150(2)
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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  O1A 0.206642(14) -0.30401(8) 0.54218(4) 0.01572(6) Uani d . 1 . O
  O2A 0.17267(2) -0.00910(9) 0.68293(4) 0.01902(7) Uani d . 1 . O
  N1A 0.197708(14) 0.08257(9) 0.34243(4) 0.01289(5) Uani d . 1 . N
  H1A 0.1974(5) -0.077(4)  0.2997(13) 0.031(3) Uiso d . 1 . H
  H2A 0.1894(5) 0.224(3)  0.2704(14) 0.029(3) Uiso d . 1 . H
  H3A 0.2299(5) 0.111(3)  0.3878(13) 0.030(3) Uiso d . 1 . H
  C1A 0.18243(2) -0.08784(9) 0.56735(4) 0.01208(6) Uani d . 1 . C
  C2A 0.161197(14) 0.08718(9) 0.44445(4) 0.01150(5) Uani d . 1 . C
  H4A 0.15646(6) 0.272(2)  0.4713(3) 0.014 Uiso calc R 1 . H
  C3A 0.11141(2) -0.03728(11) 0.38300(5) 0.01561(6) Uani d . 1 . C
  H5A 0.11615(6) -0.235(3)  0.3684(2) 0.019 Uiso calc R 1 . H
  C4A 0.07210(2) -0.0055(3) 0.48099(7) 0.0349(2) Uani d . 1 . C
  H6A 0.0841(2) -0.101(2)  0.5707(10) 0.052 Uiso calc R 1 . H
  H7A 0.0400(4) -0.099(2)  0.4406(6) 0.052 Uiso calc R 1 . H
  H8A 0.0659(3) 0.204(2)  0.4971(8) 0.052 Uiso calc R 1 . H
  C5A 0.09317(2) 0.0968(2) 0.24647(6) 0.02203(9) Uani d . 1 . C
  H9A 0.1167(2) 0.0586(16) 0.1820(6) 0.033 Uiso calc R 1 . H
  H10A 0.0899(3) 0.2994(17) 0.2576(2) 0.033 Uiso calc R 1 . H
  H11A 0.0613(3) 0.0173(14) 0.2134(5) 0.033 Uiso calc R 1 . H
  O1B 0.213289(14) 0.86726(8) 1.03905(4) 0.01529(5) Uani d . 1 . O
  O2B 0.18483(2) 0.57812(9) 1.19128(3) 0.01858(6) Uani d . 1 . O
  N1B 0.193564(15) 0.49014(9) 0.83750(4) 0.01368(5) Uani d . 1 . N
  H1B 0.1887(5) 0.664(3)  0.7928(12) 0.023(3) Uiso d . 1 . H
  H2B 0.1844(5) 0.343(3)  0.7742(14) 0.026(3) Uiso d . 1 . H
  H3B 0.2270(5) 0.471(3)  0.8663(13) 0.029(3) Uiso d . 1 . H
  C1B 0.19068(2) 0.65168(9) 1.07199(4) 0.01183(5) Uani d . 1 . C
  C2B 0.16492(2) 0.47187(9) 0.95716(4) 0.01216(5) Uani d . 1 . C
  H4B 0.16382(2) 0.279(2)  0.9862(4) 0.015 Uiso calc R 1 . H
  C3B 0.11212(2) 0.58173(12) 0.92347(5) 0.01676(7) Uani d . 1 . C
  H5B 0.09516(15) 0.5671(2) 1.0028(7) 0.020 Uiso calc R 1 . H
  H6B 0.11365(2) 0.7779(17) 0.9007(2) 0.020 Uiso calc R 1 . H
  C4B 0.08191(2) 0.4283(2) 0.80800(8) 0.02961(14) Uani d . 1 . C
  H7B 0.08095(3) 0.222(2)  0.8295(2) 0.036 Uiso calc R 1 . H
  H8B 0.0984(2) 0.4505(3) 0.7235(9) 0.036 Uiso calc R 1 . H
  C5B 0.02914(3) 0.5405(2) 0.78345(10) 0.0364(2) Uani d . 1 . C
  H9B 0.0119(2) 0.4497(19) 0.7010(11) 0.055 Uiso calc R 1 . H
  H10B 0.02992(3) 0.749(2)  0.7702(11) 0.055 Uiso calc R 1 . H
  H11B 0.0111(2) 0.496(2)  0.8630(9) 0.055 Uiso calc R 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
  O1A 0.01767(13) 0.01420(13) 0.01477(12) 0.00337(9) -0.00077(10) 0.00080(9)
  O2A 0.0310(2) 0.01698(15) 0.00912(10) 0.00090(13) 0.00219(10) -0.00071(10)
  N1A 0.01396(11) 0.01392(13) 0.01069(11) -0.00157(10) 0.00079(9) 0.00141(10)
  C1A 0.01485(13) 0.01159(14) 0.00942(12) -0.00107(10) -0.00044(10) 0.00032(9)
  C2A 0.01356(12) 0.01102(13) 0.00969(11) 0.00005(10) 0.00021(9) 0.00006(10)
  C3A 0.01359(13) 0.0189(2) 0.01393(14) -0.00217(12) -0.00049(10) 0.00024(13)
  C4A 0.0164(2) 0.0677(6) 0.0214(2) -0.0062(3) 0.0051(2) -0.0022(3)
  C5A 0.0186(2) 0.0288(3) 0.0173(2) -0.0005(2) -0.00501(14) 0.0025(2)
  O1B 0.01797(12) 0.01331(13) 0.01422(12) -0.00339(9) -0.00006(9) 0.00014(9)
  O2B 0.0309(2) 0.01552(14) 0.00936(10) -0.00114(13) 0.00240(10) 0.00084(10)
  N1B 0.01582(12) 0.01516(14) 0.00989(11) 0.00142(10) 0.00058(9) -0.00118(10)
  C1B 0.01463(13) 0.01116(14) 0.00945(12) 0.00080(10) 0.00013(9) 0.00004(9)
  C2B 0.01465(13) 0.01124(14) 0.01032(11) -0.00017(10) -0.00003(9) 0.00026(10)
  C3B 0.01383(13) 0.0190(2) 0.0171(2) 0.00080(13) -0.00004(11) -0.00123(14)
  C4B 0.0223(2) 0.0274(3) 0.0358(3) 0.0015(2) -0.0121(2) -0.0083(2)
  C5B 0.0172(2) 0.0495(5) 0.0403(4) -0.0019(2) -0.0074(2) 0.0014(3)
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
  O1A C1A . 1.2578(6) yes
  O2A C1A . 1.2643(5) yes
  N1A C2A . 1.4947(5) yes
  N1A H1A . 0.87(2) ?
  N1A H2A . 0.990(14) ?
  N1A H3A . 0.952(13) ?
  C1A C2A . 1.5391(6) yes
  C2A C3A . 1.5440(6) yes
  C2A H4A . 0.931(12) ?
  C3A C4A . 1.5300(8) yes
  C3A C5A . 1.5343(7) yes
  C3A H11A . 0.961(13) ?
  C4A H5A . 1.022(11) ?
  C4A H6A . 1.022(11) ?
  C4A H7A . 1.022(11) ?
  C5A H8A . 0.972(8) ?
  C5A H9A . 0.972(8) ?
  C5A H10A . 0.972(8) ?
  O1B C1B . 1.2543(6) yes
  O2B C1B . 1.2637(5) yes
  N1B C2B . 1.4938(5) yes
  N1B H1B . 0.938(14) ?
  N1B H2B . 0.957(15) ?
  N1B H3B . 0.930(12) ?
  C1B C2B . 1.5344(6) yes
  C2B C3B . 1.5324(6) yes
  C2B H4B . 0.961(12) ?
  C3B C4B . 1.5251(8) yes
  C3B H5B . 0.959(8) ?
  C3B H6B . 0.959(8) ?
  C4B C5B . 1.5273(10) yes
  C4B H7B . 1.000(10) ?
  C4B H8B . 1.000(10) ?
  C5B H9B . 0.998(10) ?
  C5B H10B . 0.998(10) ?
  C5B H11B . 0.998(10) ?