data_2012867
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o525
_journal_page_last  o527
_publ_section_title
;
Polymorphic forms of cilostazol
;
loop_
_publ_author_name
  'Whittall, Linda B.'
  'Whittle, Robert R.'
  'Stowell, Grayson W.'
_chemical_name_common  Cilostazol
_chemical_formula_moiety  'C20 H27 N5 O2'
_chemical_formula_sum  'C20 H27 N5 O2'
_chemical_formula_weight  369.47
_chemical_melting_point  419
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  1/2-x,1/2+y,1/2-z
  -x,-y,-z
  1/2+x,1/2-y,1/2+z
_cell_length_a  5.1480(10)
_cell_length_b  10.7390(10)
_cell_length_c  35.2790(10)
_cell_angle_alpha  90
_cell_angle_beta  94.0700(10)
_cell_angle_gamma  90
_cell_volume  1945.3(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  294
_exptl_crystal_density_diffrn  1.26
_diffrn_ambient_temperature  294
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_calc_attached_atom
_atom_site_type_symbol
  O2 1.0499(2) 0.12810(10)
  0.46767(3) 0.0866(8) Uani ? ? O
  O11 0.1660(2) 0.36120(10)
  0.61593(3) 0.0645(7) Uani ? ? O
  N1 0.7791(3) 0.12150(10)
  0.51521(3) 0.0578(8) Uani ? ? N
  N17 -0.0317(3) 0.59750(10)
  0.73305(3) 0.0632(9) Uani ? ? N
  N18 0.1507(3) 0.62950(10)
  0.76112(4) 0.0665(9) Uani ? ? N
  N19 0.1369(3) 0.55720(10)
  0.79044(4) 0.0629(9) Uani ? ? N
  N20 -0.0590(2) 0.47510(10)
  0.78118(3) 0.0503(8) Uani ? ? N
  C2 0.8942(3) 0.1806(2) 0.48742(4) 0.0610(10)
  Uani ? ? C
  C3 0.8149(3) 0.3143(2) 0.48132(4) 0.0640(10)
  Uani ? ? C
  C4 0.7883(3) 0.3818(2) 0.51839(4) 0.0540(10)
  Uani ? ? C
  C5 0.6152(3) 0.30950(10)
  0.54308(4) 0.0443(9) Uani ? ? C
  C6 0.4615(3) 0.36500(10)
  0.56880(4) 0.0480(10)
  Uani ? ? C
  C7 0.3078(3) 0.2941(2) 0.59138(4) 0.0490(10)
  Uani ? ? C
  C8 0.3034(3) 0.1662(2) 0.58768(4) 0.0550(10)
  Uani ? ? C
  C9 0.4580(3) 0.10990(10)
  0.56197(4) 0.0550(10)
  Uani ? ? C
  C10 0.6137(3) 0.1804(2) 0.54022(4) 0.0480(10)
  Uani ? ? C
  C12 0.0137(3) 0.2944(2) 0.64144(4) 0.0540(10)
  Uani ? ? C
  C13 -0.1022(3) 0.3894(2) 0.66646(4) 0.0580(10)
  Uani ? ? C
  C14 -0.2498(3) 0.3322(2) 0.69761(4) 0.0540(10)
  Uani ? ? C
  C15 -0.3635(3) 0.4281(2) 0.72403(4) 0.0540(10)
  Uani ? ? C
  C16 -0.1587(3) 0.5006(2) 0.74598(4) 0.0487(9) Uani ? ? C
  C21 -0.1289(3) 0.3820(2) 0.80926(4) 0.0520(10)
  Uani ? ? C
  C22 0.0921(3) 0.2927(2) 0.81763(5) 0.0690(10)
  Uani ? ? C
  C23 0.0298(4) 0.1996(2) 0.84818(5) 0.0850(10)
  Uani ? ? C
  C24 -0.0437(4) 0.2652(2) 0.88405(5) 0.0820(10)
  Uani ? ? C
  C25 -0.2698(4) 0.3524(2) 0.87509(5) 0.0810(10)
  Uani ? ? C
  C26 -0.2109(3) 0.4454(2) 0.84474(5) 0.0690(10)
  Uani ? ? C
  H1 0.8104 0.0346 0.5183 0.0761 Uiso calc N1 H
  H3a 0.6438 0.3169 0.4660 0.0846 Uiso calc C3 H
  H3b 0.9499 0.3574 0.4671 0.0846 Uiso calc C3 H
  H4a 0.7106 0.4659 0.5130 0.0702 Uiso calc C4 H
  H4b 0.9643 0.3915 0.5320 0.0702 Uiso calc C4 H
  H6 0.4608 0.4578 0.5712 0.0626 Uiso calc C6 H
  H8 0.1899 0.1146 0.6034 0.0707 Uiso calc C8 H
  H9 0.4562 0.0173 0.5592 0.0726 Uiso calc C9 H
  H12a 0.1264 0.2354 0.6571 0.0704 Uiso calc C12 H
  H12b -0.1276 0.2469 0.6269 0.0704 Uiso calc C12 H
  H13a -0.2246 0.4431 0.6504 0.0753 Uiso calc C13 H
  H13b 0.0417 0.4419 0.6784 0.0753 Uiso calc C13 H
  H14a -0.1283 0.2767 0.7132 0.0710 Uiso calc C14 H
  H14b -0.3963 0.2814 0.6856 0.0710 Uiso calc C14 H
  H15a -0.4708 0.3834 0.7423 0.0704 Uiso calc C15 H
  H15b -0.4766 0.4870 0.7083 0.0704 Uiso calc C15 H
  H21 -0.2812 0.3325 0.7985 0.0678 Uiso calc C21 H
  H22a 0.2514 0.3408 0.8265 0.0906 Uiso calc C22 H
  H22b 0.1256 0.2465 0.7938 0.0906 Uiso calc C22 H
  H23a 0.1864 0.1463 0.8544 0.1133 Uiso calc C23 H
  H23b -0.1190 0.1461 0.8383 0.1133 Uiso calc C23 H
  H24a 0.1091 0.3140 0.8950 0.1118 Uiso calc C24 H
  H24b -0.0941 0.2017 0.9029 0.1118 Uiso calc C24 H
  H25a -0.3077 0.3985 0.8987 0.1119 Uiso calc C25 H
  H25b -0.4260 0.3024 0.8660 0.1119 Uiso calc C25 H
  H26a -0.3706 0.4961 0.8381 0.0899 Uiso calc C26 H
  H26b -0.0670 0.5013 0.8549 0.0899 Uiso calc C26 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
_atom_site_aniso_type_symbol
  O2 0.1240(10)
  0.0741(9) 0.0710(7) 0.0248(8) 0.0518(6) 0.0070(7) O
  O11 0.0722(7) 0.0555(7) 0.0670(7) 0.0043(6) 0.0314(6) -0.0014(6) O
  N1 0.0830(10)
  0.0457(8) 0.0510(8) 0.0106(8) 0.0246(7) 0.0019(7) N
  N17 0.0720(10)
  0.0615(9) 0.0570(8) -0.0094(9) 0.0151(7) 0.0014(8) N
  N18 0.0750(10)
  0.0610(10)
  0.0647(9) -0.0139(8) 0.0177(7) -0.0018(8) N
  N19 0.0670(9) 0.0612(9) 0.0606(9) -0.0167(8) 0.0102(7) -0.0062(8) N
  N20 0.0561(8) 0.0498(8) 0.0456(7) -0.0087(7) 0.0100(6) -0.0029(7) N
  C2 0.0820(10)
  0.0600(10)
  0.0461(9) 0.0100(10)
  0.0158(9) 0.0015(9) C
  C3 0.0860(10)
  0.0600(10)
  0.0510(10)
  0.0050(10)
  0.0185(9) 0.0065(9) C
  C4 0.0550(10)
  0.0550(10)
  0.0530(10)
  0.0011(9) 0.0098(8) 0.0040(9) C
  C5 0.0445(9) 0.0460(10)
  0.0422(9) 0.0026(9) 0.0030(8) 0.0002(8) C
  C6 0.0520(10)
  0.0420(10)
  0.0502(9) 0.0023(9) 0.0058(8) 0.0001(8) C
  C7 0.0490(10)
  0.0520(10)
  0.0461(9) 0.0068(9) 0.0083(8) -0.0031(8) C
  C8 0.0580(10)
  0.0500(10)
  0.0560(10)
  -0.0005(9) 0.0148(8) 0.0026(9) C
  C9 0.0710(10)
  0.0430(10)
  0.0550(10)
  0.0000(10)
  0.0158(9) -0.0017(9) C
  C10 0.0530(10)
  0.0500(10)
  0.0421(9) 0.0075(9) 0.0065(8) -0.0005(8) C
  C12 0.0550(10)
  0.0600(10)
  0.0488(9) 0.0000(10)
  0.0119(8) 0.0016(9) C
  C13 0.0640(10)
  0.0600(10)
  0.0511(9) 0.0010(10)
  0.0163(9) -0.0031(9) C
  C14 0.0550(10)
  0.0640(10)
  0.0462(9) -0.0070(10)
  0.0073(8) -0.0019(9) C
  C15 0.0540(10)
  0.0660(10)
  0.0442(9) -0.0020(10)
  0.0102(8) 0.0016(9) C
  C16 0.0540(10)
  0.0510(10)
  0.0418(8) 0.0027(9) 0.0142(7) -0.0017(8) C
  C21 0.0590(10)
  0.0560(10)
  0.0420(9) -0.0143(9) 0.0067(8) -0.0014(9) C
  C22 0.0840(10)
  0.0610(10)
  0.0650(10)
  0.0110(10)
  0.0140(10)
  0.0040(10)
  C
  C23 0.111(2) 0.0720(10)
  0.0780(10)
  0.0020(10)
  0.0040(10)
  0.0170(10)
  C
  C24 0.0880(10)
  0.112(2) 0.0570(10)
  -0.0240(10)
  -0.0060(10)
  0.0230(10)
  C
  C25 0.0810(10)
  0.127(2) 0.0510(10)
  -0.0070(10)
  0.0130(10)
  0.0140(10)
  C
  C26 0.0730(10)
  0.0840(10)
  0.0530(10)
  0.0080(10)
  0.0205(9) -0.0010(10)
  C
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
  O2 C2 . . 1.234(2) ?
  O11 C7 . . 1.375(2) ?
  O11 C12 . . 1.428(2) ?
  N1 C2 . . 1.341(2) ?
  N1 C10 . . 1.418(2) ?
  N1 H1 . . 0.952 ?
  N17 N18 . . 1.360(2) ?
  N17 C16 . . 1.326(2) ?
  N18 N19 . . 1.300(2) ?
  N19 N20 . . 1.362(2) ?
  N20 C16 . . 1.338(2) ?
  N20 C21 . . 1.470(2) ?
  C2 C3 . . 1.504(3) ?
  C3 C4 . . 1.510(2) ?
  C3 H3a . . 1.000 ?
  C3 H3b . . 1.000 ?
  C4 C5 . . 1.505(2) ?
  C4 H4a . . 1.000 ?
  C4 H4b . . 1.000 ?
  C5 C6 . . 1.381(2) ?
  C5 C10 . . 1.391(2) ?
  C6 C7 . . 1.389(2) ?
  C6 H6 . . 1.000 ?
  C7 C8 . . 1.380(3) ?
  C8 C9 . . 1.387(2) ?
  C8 H8 . . 1.000 ?
  C9 C10 . . 1.375(2) ?
  C9 H9 . . 1.000 ?
  C12 C13 . . 1.500(2) ?
  C12 H12a . . 1.000 ?
  C12 H12b . . 1.000 ?
  C13 C14 . . 1.510(2) ?
  C13 H13a . . 1.000 ?
  C13 H13b . . 1.000 ?
  C14 C15 . . 1.533(2) ?
  C14 H14a . . 1.000 ?
  C14 H14b . . 1.000 ?
  C15 C16 . . 1.484(2) ?
  C15 H15a . . 1.000 ?
  C15 H15b . . 1.000 ?
  C21 C22 . . 1.502(5) ?
  C21 C26 . . 1.511(2) ?
  C21 H21 . . 1.000 ?
  C22 C23 . . 1.521(3) ?
  C22 H22a . . 1.000 ?
  C22 H22b . . 1.000 ?
  C23 C24 . . 1.520(3) ?
  C23 H23a . . 1.000 ?
  C23 H23b . . 1.000 ?
  C24 C25 . . 1.510(3) ?
  C24 H24a . . 1.000 ?
  C24 H24b . . 1.000 ?
  C25 C26 . . 1.511(3) ?
  C25 H25a . . 1.000 ?
  C25 H25b . . 1.000 ?
  C26 H26a . . 1.000 ?
  C26 H26b . . 1.000 ?