data_2014633
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2005
_journal_volume  61
_journal_page_first  o174
_journal_page_last  o176
_publ_section_title
;
Cyclo(-<i>L</i>-leucyl-\a,\b-dehydrophenyalanine): the first diketopiperazine
containing an \a,\b-dehydrophenylalanine residue
;
loop_
_publ_author_name
  'Bagaria, A.'
  'Ramakumar, S.'
  'Gupta, M.'
  'Chauhan, V. S.'
_chemical_name_common  Leu-Phe*
_chemical_formula_moiety  'C15 H18 N2 O2'
_chemical_formula_sum  'C15 H18 N2 O2'
_chemical_formula_iupac  'C15 H18 N2 O2'
_chemical_formula_weight  258.31
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P 1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
_cell_length_a  6.2384(5)
_cell_length_b  9.8255(7)
_cell_length_c  12.5432(9)
_cell_angle_alpha  69.3440(10)
_cell_angle_beta  78.0540(10)
_cell_angle_gamma  79.3960(10)
_cell_volume  698.64(9)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.228
_diffrn_ambient_temperature  293(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_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
  N1A 0.9884(3) 0.2550(3) 1.0321(2) 0.0466(6) Uani d . 1 . . N
  H1A 1.1142 0.2154 1.0534 0.056 Uiso calc R 1 . . H
  C1A 0.7985(4) 0.1831(3) 1.1016(2) 0.0428(6) Uani d . 1 . . C
  H1A1 0.8302 0.0797 1.1067 0.051 Uiso calc R 1 . . H
  C1'A 0.5898(4) 0.2451(3) 1.0481(2) 0.0437(6) Uani d . 1 . . C
  O1'A 0.4266(3) 0.1813(3) 1.0904(2) 0.0641(7) Uani d . 1 . . O
  C1BA 0.7572(5) 0.1887(4) 1.2243(3) 0.0535(7) Uani d . 1 . . C
  H1B1 0.7205 0.2904 1.2208 0.064 Uiso calc R 1 . . H
  H1B2 0.6296 0.1387 1.2664 0.064 Uiso calc R 1 . . H
  C1GA 0.9479(6) 0.1215(4) 1.2922(3) 0.0678(9) Uani d . 1 . . C
  H1GA 1.0744 0.1750 1.2506 0.081 Uiso calc R 1 . . H
  C1D1 0.8873(9) 0.1409(6) 1.4102(4) 0.0969(15) Uani d . 1 . . C
  H1D1 0.7778 0.0784 1.4567 0.145 Uiso calc R 1 . . H
  H1D2 0.8295 0.2412 1.4015 0.145 Uiso calc R 1 . . H
  H1D3 1.0165 0.1155 1.4469 0.145 Uiso calc R 1 . . H
  C2D1 1.0160(9) -0.0366(6) 1.3032(4) 0.1013(16) Uani d . 1 . . C
  H2D1 0.8887 -0.0886 1.3320 0.152 Uiso calc R 1 . . H
  H2D2 1.1212 -0.0780 1.3557 0.152 Uiso calc R 1 . . H
  H2D3 1.0816 -0.0445 1.2290 0.152 Uiso calc R 1 . . H
  N2A 0.5900(3) 0.3705(3) 0.9574(2) 0.0430(5) Uani d . 1 . . N
  H2A 0.4661 0.4088 0.9334 0.052 Uiso calc R 1 . . H
  C2'A 0.9912(4) 0.3740(3) 0.9399(2) 0.0409(6) Uani d . 1 . . C
  O2'A 1.1616(3) 0.4289(2) 0.88938(18) 0.0558(6) Uani d . 1 . . O
  C2A 0.7745(4) 0.4437(3) 0.8990(2) 0.0398(6) Uani d . 1 . . C
  C2B 0.5053(4) 0.8979(3) 0.9907(2) 0.0396(6) Uani d . 1 . . C
  C2GA 0.5936(5) 0.6660(3) 0.7550(3) 0.0477(7) Uani d . 1 . . C
  C1DA 0.3912(5) 0.6960(3) 0.8173(3) 0.0530(7) Uani d . 1 . . C
  H1DA 0.3664 0.6521 0.8969 0.064 Uiso calc R 1 . . H
  C2DA 0.6273(5) 0.7377(4) 0.6367(3) 0.0614(8) Uani d . 1 . . C
  H2DA 0.7644 0.7223 0.5936 0.074 Uiso calc R 1 . . H
  C1EA 0.2247(6) 0.7917(4) 0.7614(4) 0.0652(9) Uani d . 1 . . C
  H1EA 0.0890 0.8115 0.8039 0.078 Uiso calc R 1 . . H
  C2EA 0.4597(7) 0.8317(4) 0.5822(3) 0.0737(11) Uani d . 1 . . C
  H2EA 0.4840 0.8780 0.5028 0.088 Uiso calc R 1 . . H
  C2ZA 0.2590(6) 0.8566(4) 0.6445(4) 0.0719(11) Uani d . 1 . . C
  H2ZA 0.1452 0.9179 0.6073 0.086 Uiso calc R 1 . . H
  N1B 0.3035(3) 1.0695(2) 0.8440(2) 0.0445(6) Uani d . 1 . . N
  H1B 0.1806 1.1183 0.8240 0.053 Uiso calc R 1 . . H
  C1BB 0.4838(4) 1.2735(3) 0.6951(2) 0.0437(6) Uani d . 1 . . C
  H1B3 0.4810 1.3248 0.7489 0.052 Uiso calc R 1 . . H
  H1B4 0.6160 1.2932 0.6385 0.052 Uiso calc R 1 . . H
  C1'B 0.7071(4) 1.0617(3) 0.8187(2) 0.0441(6) Uani d . 1 . . C
  O1'B 0.8776(3) 1.1129(3) 0.7679(2) 0.0697(8) Uani d . 1 . . O
  C1B 0.5010(4) 1.1087(3) 0.7614(2) 0.0394(6) Uani d . 1 . . C
  H1B5 0.5169 1.0572 0.7054 0.047 Uiso calc R 1 . . H
  C1GB 0.2835(5) 1.3372(3) 0.6332(3) 0.0504(7) Uani d . 1 . . C
  H1GB 0.1510 1.3187 0.6913 0.060 Uiso calc R 1 . . H
  C1D2 0.2824(6) 1.5022(4) 0.5794(4) 0.0704(10) Uani d . 1 . . C
  H1D4 0.4123 1.5235 0.5231 0.106 Uiso calc R 1 . . H
  H1D5 0.2805 1.5437 0.6384 0.106 Uiso calc R 1 . . H
  H1D6 0.1536 1.5435 0.5429 0.106 Uiso calc R 1 . . H
  C2D2 0.2716(9) 1.2710(5) 0.5450(4) 0.0888(13) Uani d . 1 . . C
  H2D4 0.4029 1.2837 0.4887 0.133 Uiso calc R 1 . . H
  H2D5 0.1450 1.3182 0.5078 0.133 Uiso calc R 1 . . H
  H2D6 0.2592 1.1683 0.5816 0.133 Uiso calc R 1 . . H
  N2B 0.6958(3) 0.9595(3) 0.9243(2) 0.0440(5) Uani d . 1 . . N
  H2B 0.8159 0.9294 0.9536 0.053 Uiso calc R 1 . . H
  C2BA 0.7767(4) 0.5675(3) 0.8094(2) 0.0481(7) Uani d . 1 . . C
  H2BA 0.9161 0.5959 0.7762 0.058 Uiso calc R 1 . . H
  C2'B 0.2917(4) 0.9662(3) 0.9473(2) 0.0402(6) Uani d . 1 . . C
  O2'B 0.1152(3) 0.9275(2) 1.00565(18) 0.0510(5) Uani d . 1 . . O
  C2BB 0.5022(4) 0.7878(3) 1.0902(2) 0.0461(7) Uani d . 1 . . C
  H2BB 0.3633 0.7635 1.1291 0.055 Uiso calc R 1 . . H
  C2GB 0.6909(4) 0.6995(3) 1.1463(2) 0.0462(6) Uani d . 1 . . C
  C1DB 0.8765(5) 0.6407(3) 1.0870(3) 0.0534(7) Uani d . 1 . . C
  H1DB 0.8857 0.6591 1.0083 0.064 Uiso calc R 1 . . H
  C2DB 0.6814(6) 0.6686(5) 1.2634(3) 0.0746(11) Uani d . 1 . . C
  H2DB 0.5575 0.7047 1.3056 0.090 Uiso calc R 1 . . H
  C1EB 1.0476(6) 0.5552(4) 1.1434(3) 0.0639(9) Uani d . 1 . . C
  H1EB 1.1699 0.5157 1.1025 0.077 Uiso calc R 1 . . H
  C2EB 0.8562(8) 0.5838(6) 1.3185(3) 0.0928(14) Uani d . 1 . . C
  H2EB 0.8493 0.5647 1.3971 0.111 Uiso calc R 1 . . H
  C2ZB 1.0385(6) 0.5283(5) 1.2580(4) 0.0744(11) Uani d . 1 . . C
  H2ZB 1.1556 0.4724 1.2952 0.089 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
  N1A 0.0218(10) 0.0564(14) 0.0521(14) -0.0020(9) -0.0152(9) -0.0022(11)
  C1A 0.0261(12) 0.0472(15) 0.0506(16) -0.0045(10) -0.0137(11) -0.0059(12)
  C1'A 0.0260(12) 0.0523(15) 0.0496(15) -0.0030(11) -0.0139(11) -0.0090(13)
  O1'A 0.0297(10) 0.0692(14) 0.0762(15) -0.0148(9) -0.0205(10) 0.0086(12)
  C1BA 0.0420(14) 0.0640(19) 0.0490(16) -0.0100(13) -0.0108(12) -0.0077(14)
  C1GA 0.0538(18) 0.087(3) 0.0528(18) -0.0186(17) -0.0213(14) 0.0015(17)
  C1D1 0.124(4) 0.109(4) 0.058(2) -0.035(3) -0.035(2) -0.005(2)
  C2D1 0.101(3) 0.105(4) 0.082(3) 0.027(3) -0.045(3) -0.013(3)
  N2A 0.0238(10) 0.0532(14) 0.0470(12) -0.0014(9) -0.0152(9) -0.0065(11)
  C2'A 0.0241(12) 0.0552(16) 0.0416(14) -0.0063(11) -0.0089(10) -0.0108(12)
  O2'A 0.0281(9) 0.0723(14) 0.0551(12) -0.0114(9) -0.0143(8) 0.0008(11)
  C2A 0.0287(12) 0.0499(16) 0.0399(14) -0.0040(11) -0.0122(10) -0.0099(12)
  C2B 0.0293(12) 0.0453(14) 0.0425(14) -0.0052(10) -0.0099(10) -0.0095(12)
  C2GA 0.0422(15) 0.0432(14) 0.0567(17) -0.0062(12) -0.0220(13) -0.0063(13)
  C1DA 0.0475(16) 0.0486(16) 0.0593(18) -0.0034(13) -0.0148(13) -0.0110(14)
  C2DA 0.0551(18) 0.0587(19) 0.0565(18) -0.0098(15) -0.0140(15) 0.0026(15)
  C1EA 0.0481(17) 0.0477(17) 0.095(3) 0.0054(14) -0.0245(17) -0.0153(18)
  C2EA 0.087(3) 0.060(2) 0.063(2) -0.0091(19) -0.038(2) 0.0082(17)
  C2ZA 0.064(2) 0.0466(17) 0.100(3) 0.0004(15) -0.046(2) -0.0034(18)
  N1B 0.0243(10) 0.0475(13) 0.0511(13) -0.0030(9) -0.0142(9) 0.0008(11)
  C1BB 0.0362(13) 0.0454(14) 0.0446(14) -0.0097(11) -0.0114(10) -0.0035(11)
  C1'B 0.0251(12) 0.0490(15) 0.0479(15) -0.0054(11) -0.0086(11) -0.0011(12)
  O1'B 0.0294(10) 0.0852(17) 0.0657(13) -0.0138(10) -0.0170(9) 0.0190(12)
  C1B 0.0288(12) 0.0431(14) 0.0418(14) -0.0040(10) -0.0110(10) -0.0054(11)
  C1GB 0.0400(14) 0.0487(16) 0.0513(16) -0.0072(12) -0.0172(12) 0.0037(13)
  C1D2 0.072(2) 0.0491(18) 0.076(2) -0.0004(16) -0.0243(18) 0.0001(16)
  C2D2 0.122(4) 0.065(2) 0.092(3) 0.003(2) -0.066(3) -0.019(2)
  N2B 0.0274(10) 0.0497(13) 0.0465(12) -0.0047(9) -0.0153(9) 0.0001(10)
  C2BA 0.0319(13) 0.0582(17) 0.0495(16) -0.0097(12) -0.0128(12) -0.0064(14)
  C2'B 0.0289(13) 0.0416(14) 0.0473(15) -0.0049(11) -0.0123(11) -0.0073(12)
  O2'B 0.0286(9) 0.0593(12) 0.0533(12) -0.0097(8) -0.0095(8) -0.0001(10)
  C2BB 0.0342(13) 0.0507(16) 0.0475(16) -0.0079(12) -0.0112(11) -0.0050(13)
  C2GB 0.0419(14) 0.0450(15) 0.0437(15) -0.0107(12) -0.0141(11) 0.0022(12)
  C1DB 0.0546(17) 0.0501(17) 0.0481(16) -0.0029(13) -0.0163(13) -0.0041(13)
  C2DB 0.066(2) 0.092(3) 0.0473(18) 0.0070(19) -0.0149(16) -0.0052(18)
  C1EB 0.0498(17) 0.0542(18) 0.071(2) 0.0005(14) -0.0165(16) 0.0005(16)
  C2EB 0.099(3) 0.114(4) 0.049(2) 0.009(3) -0.038(2) -0.003(2)
  C2ZB 0.062(2) 0.073(2) 0.072(2) 0.0017(18) -0.0350(18) 0.0061(18)
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
  N1A C1A . 1.452(3) ?
  N1A C2'A . 1.323(3) ?
  N1A H1A . 0.8600 ?
  C1A C1'A . 1.516(3) ?
  C1A C1BA . 1.526(4) ?
  C1A H1A1 . 0.9800 ?
  C1'A O1'A . 1.220(3) ?
  C1'A N2A . 1.350(4) ?
  C1BA C1GA . 1.519(4) ?
  C1BA H1B1 . 0.9700 ?
  C1BA H1B2 . 0.9700 ?
  C1GA C2D1 . 1.497(7) ?
  C1GA C1D1 . 1.521(6) ?
  C1GA H1GA . 0.9800 ?
  C1D1 H1D1 . 0.9600 ?
  C1D1 H1D2 . 0.9600 ?
  C1D1 H1D3 . 0.9600 ?
  C2D1 H2D1 . 0.9600 ?
  C2D1 H2D2 . 0.9600 ?
  C2D1 H2D3 . 0.9600 ?
  N2A C2A . 1.400(3) ?
  N2A H2A . 0.8600 ?
  C2'A O2'A . 1.230(3) ?
  C2'A C2A . 1.503(3) ?
  C2A C2BA . 1.333(4) ?
  C2B C2BB . 1.332(4) ?
  C2B N2B . 1.404(3) ?
  C2B C2'B . 1.495(3) ?
  C2GA C1DA . 1.381(4) ?
  C2GA C2DA . 1.390(4) ?
  C2GA C2BA . 1.469(4) ?
  C1DA C1EA . 1.390(4) ?
  C1DA H1DA . 0.9300 ?
  C2DA C2EA . 1.381(5) ?
  C2DA H2DA . 0.9300 ?
  C1EA C2ZA . 1.365(6) ?
  C1EA H1EA . 0.9300 ?
  C2EA C2ZA . 1.362(6) ?
  C2EA H2EA . 0.9300 ?
  C2ZA H2ZA . 0.9300 ?
  N1B C1B . 1.451(3) ?
  N1B C2'B . 1.333(3) ?
  N1B H1B . 0.8600 ?
  C1BB C1GB . 1.526(3) ?
  C1BB C1B . 1.532(4) ?
  C1BB H1B3 . 0.9700 ?
  C1BB H1B4 . 0.9700 ?
  C1'B O1'B . 1.217(3) ?
  C1'B N2B . 1.348(4) ?
  C1'B C1B . 1.521(3) ?
  C1B H1B5 . 0.9800 ?
  C1GB C2D2 . 1.487(5) ?
  C1GB C1D2 . 1.519(5) ?
  C1GB H1GB . 0.9800 ?
  C1D2 H1D4 . 0.9600 ?
  C1D2 H1D5 . 0.9600 ?
  C1D2 H1D6 . 0.9600 ?
  C2D2 H2D4 . 0.9600 ?
  C2D2 H2D5 . 0.9600 ?
  C2D2 H2D6 . 0.9600 ?
  N2B H2B . 0.8600 ?
  C2BA H2BA . 0.9300 ?
  C2'B O2'B . 1.231(3) ?
  C2BB C2GB . 1.474(4) ?
  C2BB H2BB . 0.9300 ?
  C2GB C2DB . 1.382(5) ?
  C2GB C1DB . 1.388(4) ?
  C1DB C1EB . 1.382(4) ?
  C1DB H1DB . 0.9300 ?
  C2DB C2EB . 1.390(5) ?
  C2DB H2DB . 0.9300 ?
  C1EB C2ZB . 1.357(6) ?
  C1EB H1EB . 0.9300 ?
  C2EB C2ZB . 1.369(6) ?
  C2EB H2EB . 0.9300 ?
  C2ZB H2ZB . 0.9300 ?