data_2008943
_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  'C6 H13 N O2 . C5 H11 N O2'
_chemical_formula_sum  'C11 H24 N2 O4 '
_chemical_formula_structural  'C6 H13 N O2 . C5 H11 N O2'
_chemical_formula_weight  248.32
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
_cell_length_a  5.16390(10)
_cell_length_b  5.40760(10)
_cell_length_c  13.1241(2)
_cell_angle_alpha  91.7790(10)
_cell_angle_beta  98.1380(10)
_cell_angle_gamma  111.8230(10)
_cell_volume  335.390(10)
_cell_formula_units_Z  1
_cell_measurement_temperature  150(2)
_exptl_crystal_density_diffrn  1.229
_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 0.5788(2) 0.9151(2) 0.52397(9) 0.0181(2) Uani d . 1 . O
  O2A 0.1321(2) 0.7755(2) 0.55364(8) 0.0168(2) Uani d . 1 . O
  N1A 0.5575(2) 0.4088(2) 0.50608(9) 0.0131(2) Uani d . 1 . N
  H1A 0.726(6)  0.522(5)  0.5226(19) 0.023(6) Uiso d . 1 . H
  H2A 0.548(5)  0.239(5)  0.5068(17) 0.015(5) Uiso d . 1 . H
  H3A 0.492(5)  0.422(5)  0.4414(16) 0.014(5) Uiso d . 1 . H
  C1A 0.3582(3) 0.7437(2) 0.54732(9) 0.0117(2) Uani d . 1 . C
  C2A 0.3744(3) 0.4720(2) 0.57269(9) 0.0115(2) Uani d . 1 . C
  H4A 0.215(4)  0.355(3)  0.5612(3) 0.014 Uiso calc R 1 . H
  C3A 0.5048(3) 0.4827(3) 0.68594(11) 0.0162(3) Uani d . 1 . C
  H5A 0.690(3)  0.645(3)  0.7015(3) 0.019 Uiso calc R 1 . H
  H6A 0.5521(9) 0.318(3)  0.6955(2) 0.019 Uiso calc R 1 . H
  C4A 0.3175(4) 0.4973(3) 0.76487(11) 0.0200(3) Uani d . 1 . C
  H7A 0.227(2)  0.633(3)  0.7434(5) 0.024 Uiso calc R 1 . H
  C5A 0.0820(4) 0.2272(4) 0.76885(14) 0.0280(4) Uani d . 1 . C
  H8A -0.049(3)  0.2483(8) 0.8142(13) 0.042 Uiso calc R 1 . H
  H9A 0.1653(17) 0.099(3)  0.7970(13) 0.042 Uiso calc R 1 . H
  H10A -0.024(3)  0.157(2)  0.6979(14) 0.042 Uiso calc R 1 . H
  C6A 0.5026(4) 0.5979(4) 0.87189(12) 0.0388(4) Uani d . 1 . C
  H11A 0.641(4)  0.768(4)  0.8689(4) 0.058 Uiso calc R 1 . H
  H12A 0.591(4)  0.479(3)  0.8915(8) 0.058 Uiso calc R 1 . H
  H13A 0.389(3)  0.608(4)  0.9205(11) 0.058 Uiso calc R 1 . H
  O1B -0.1159(2) 0.3973(2) 0.33813(9) 0.0188(2) Uani d . 1 . O
  O2B 0.3291(2) 0.5335(2) 0.30759(8) 0.0169(2) Uani d . 1 . O
  N1B -0.0983(3) 0.9004(2) 0.35442(10) 0.0145(2) Uani d . 1 . N
  H1B -0.290(5)  0.786(5)  0.3366(17) 0.018(5) Uiso d . 1 . H
  H2B -0.089(7)  1.061(7)  0.342(2)  0.036(7) Uiso d . 1 . H
  H3B -0.073(5)  0.873(5)  0.4232(19) 0.024(6) Uiso d . 1 . H
  C1B 0.1035(3) 0.5695(3) 0.31442(9) 0.0122(2) Uani d . 1 . C
  C2B 0.0913(3) 0.8409(3) 0.29012(10) 0.0141(2) Uani d . 1 . C
  H4B 0.304(4)  0.998(3)  0.3076(3) 0.017 Uiso calc R 1 . H
  C3B -0.0334(4) 0.8326(4) 0.17505(12) 0.0221(3) Uani d . 1 . C
  H5B -0.218(4)  0.669(3)  0.1577(4) 0.027 Uiso calc R 1 . H
  H6B -0.0811(11) 0.998(3)  0.1650(2) 0.027 Uiso calc R 1 . H
  C4B 0.1611(5) 0.8216(4) 0.09891(13) 0.0278(4) Uani d . 1 . C
  H7B 0.054(2)  0.7591(15) 0.0336(15) 0.033 Uiso calc R 1 . H
  H8B 0.245(2)  0.702(3)  0.1189(5) 0.033 Uiso calc R 1 . H
  C5B 0.3912(6) 1.0961(5) 0.0938(2) 0.0375(5) Uani d . 1 . C
  H9B 0.511(4)  1.0823(10) 0.0397(16) 0.056 Uiso calc R 1 . H
  H10B 0.518(4)  1.160(2)  0.1647(17) 0.056 Uiso calc R 1 . H
  H11B 0.299(2)  1.230(3)  0.0736(16) 0.056 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 0.0175(5) 0.0104(4) 0.0310(5) 0.0078(3) 0.0106(4) 0.0061(4)
  O2A 0.0128(4) 0.0142(4) 0.0261(5) 0.0083(3) 0.0033(4) 0.0024(4)
  N1A 0.0148(5) 0.0084(4) 0.0179(5) 0.0052(3) 0.0057(4) 0.0027(4)
  C1A 0.0132(5) 0.0087(4) 0.0150(5) 0.0060(4) 0.0027(4) 0.0020(4)
  C2A 0.0120(5) 0.0079(4) 0.0163(5) 0.0049(4) 0.0041(4) 0.0025(4)
  C3A 0.0156(5) 0.0167(6) 0.0170(5) 0.0072(4) 0.0019(4) 0.0032(4)
  C4A 0.0267(7) 0.0191(6) 0.0179(5) 0.0116(5) 0.0072(5) 0.0035(5)
  C5A 0.0260(8) 0.0314(9) 0.0276(7) 0.0089(6) 0.0113(6) 0.0100(6)
  C6A 0.0512(9) 0.0366(7) 0.0188(5) 0.0051(6) 0.0078(5) 0.0002(5)
  O1B 0.0169(5) 0.0104(4) 0.0317(6) 0.0055(3) 0.0102(4) 0.0065(4)
  O2B 0.0141(4) 0.0159(5) 0.0241(5) 0.0088(4) 0.0042(4) 0.0032(4)
  N1B 0.0154(5) 0.0105(4) 0.0211(5) 0.0075(4) 0.0069(4) 0.0042(4)
  C1B 0.0127(5) 0.0101(5) 0.0148(5) 0.0055(4) 0.0019(4) 0.0010(4)
  C2B 0.0134(5) 0.0110(5) 0.0201(6) 0.0061(4) 0.0054(4) 0.0036(4)
  C3B 0.0273(8) 0.0248(7) 0.0206(6) 0.0157(6) 0.0069(5) 0.0086(5)
  C4B 0.0361(9) 0.0310(9) 0.0204(6) 0.0161(7) 0.0075(6) 0.0045(6)
  C5B 0.0376(11) 0.0390(12) 0.0377(10) 0.0117(9) 0.0175(8) 0.0127(8)
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 . 1.258(2) yes
  O2A C1A . 1.255(2) yes
  N1A C2A . 1.493(2) yes
  N1A H1A . 0.85(3) ?
  N1A H2A . 0.90(2) ?
  N1A H3A . 0.88(2) ?
  C1A C2A . 1.546(2) yes
  C2A C3A . 1.532(2) yes
  C2A H4A . 0.82(2) ?
  C3A C4A . 1.533(2) yes
  C3A H5A . 1.02(2) ?
  C3A H6A . 1.02(2) ?
  C4A C5A . 1.522(3) yes
  C4A C6A . 1.539(2) yes
  C4A H7A . 1.03(2) ?
  C5A H8A . 1.00(2) ?
  C5A H9A . 1.00(2) ?
  C5A H10A . 1.00(2) ?
  C6A H11A . 0.94(2) ?
  C6A H12A . 0.94(2) ?
  C6A H13A . 0.94(2) ?
  O1B C1B . 1.257(2) yes
  O2B C1B . 1.265(2) yes
  N1B C2B . 1.492(2) yes
  N1B H1B . 0.94(2) ?
  N1B H2B . 0.87(3) ?
  N1B H3B . 0.92(2) ?
  C1B C2B . 1.534(2) yes
  C2B C3B . 1.548(2) yes
  C2B H4B . 1.10(2) ?
  C3B C4B . 1.528(3) yes
  C3B H5B . 1.02(2) ?
  C3B H6B . 1.02(2) ?
  C4B C5B . 1.529(3) yes
  C4B H7B . 0.93(2) ?
  C4B H8B . 0.93(2) ?
  C5B H9B . 1.03(2) ?
  C5B H10B . 1.03(2) ?
  C5B H11B . 1.03(2) ?