data_2012866
_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  432
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  'x,y,z'
  1/2-x,-y,1/2+z
  -x,1/2+y,1/2-z
  1/2+x,1/2-y,-z
  -x,-y,-z
  1/2+x,+y,1/2-z
  +x,1/2-y,1/2+z
  1/2-x,1/2+y,+z
_cell_length_a  11.3240(10)
_cell_length_b  9.8550(10)
_cell_length_c  35.0120(10)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  3907.3(5)
_cell_formula_units_Z  8
_cell_measurement_temperature  294.0(10)
_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_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_occupancy
_atom_site_type_symbol
  O2 0.62329(9) 1.01670(10)
  0.53035(4) 0.0916(7) Uani ? ? 1.000 O
  O11 0.81141(7) 0.52716(9) 0.37410(3) 0.0619(6) Uani ? ? 1.000 O
  N1 0.61020(10)
  0.87960(10)
  0.47935(4) 0.0577(7) Uani ? ? 1.000 N
  N17 0.55640(10)
  0.16020(10)
  0.24818(4) 0.0714(8) Uani ? ? 1.000 N
  N18 0.53220(10)
  0.08440(10)
  0.21678(4) 0.0715(8) Uani ? ? 1.000 N
  N19 0.59340(10)
  0.12520(10)
  0.18792(4) 0.0647(7) Uani ? ? 1.000 N
  N20 0.65938(9) 0.23081(9) 0.20057(3) 0.0493(6) Uani ? ? 1.000 N
  C2 0.66910(10)
  0.9323(2) 0.50875(5) 0.0689(9) Uani ? ? 1.000 C
  C3 0.7882(2) 0.8711(2) 0.51669(6) 0.0650(10)
  Uani ? ? 0.800 C
  C4 0.8548(2) 0.8434(2) 0.47936(6) 0.0570(10)
  Uani ? ? 0.800 C
  C5 0.77900(10)
  0.76010(10)
  0.45332(4) 0.0506(8) Uani ? ? 1.000 C
  C6 0.82450(10)
  0.66970(10)
  0.42701(4) 0.0532(8) Uani ? ? 1.000 C
  C7 0.75300(10)
  0.60740(10)
  0.40002(4) 0.0503(8) Uani ? ? 1.000 C
  C8 0.63290(10)
  0.63190(10)
  0.40015(4) 0.0557(8) Uani ? ? 1.000 C
  C9 0.58650(10)
  0.72130(10)
  0.42684(5) 0.0563(8) Uani ? ? 1.000 C
  C10 0.65820(10)
  0.78550(10)
  0.45302(4) 0.0497(8) Uani ? ? 1.000 C
  C12 0.74340(10)
  0.44910(10)
  0.34773(4) 0.0543(8) Uani ? ? 1.000 C
  C13 0.82800(10)
  0.38230(10)
  0.32055(5) 0.0625(9) Uani ? ? 1.000 C
  C14 0.76680(10)
  0.28560(10)
  0.29316(5) 0.0655(9) Uani ? ? 1.000 C
  C15 0.69150(10)
  0.35260(10)
  0.26309(5) 0.0605(9) Uani ? ? 1.000 C
  C16 0.63580(10)
  0.25140(10)
  0.23751(4) 0.0525(8) Uani ? ? 1.000 C
  C21 0.74630(10)
  0.29460(10)
  0.17484(4) 0.0493(8) Uani ? ? 1.000 C
  C22 0.85580(10)
  0.20700(10)
  0.17191(5) 0.0567(8) Uani ? ? 1.000 C
  C23 0.94580(10)
  0.27100(10)
  0.14548(5) 0.0650(10)
  Uani ? ? 1.000 C
  C24 0.89360(10)
  0.30090(10)
  0.10667(5) 0.0720(10)
  Uani ? ? 1.000 C
  C25 0.78390(10)
  0.38890(10)
  0.11007(5) 0.0690(10)
  Uani ? ? 1.000 C
  C26 0.69290(10)
  0.32380(10)
  0.13606(5) 0.0593(9) Uani ? ? 1.000 C
  C3A 0.8115 0.9432 0.5000 0.0577 Uani ? ? 0.200 C
  C4A 0.8475 0.8030 0.4916 0.0449 Uani ? ? 0.200 C
  H1 0.5305 0.9070 0.4758 0.0753 Uiso calc N1 1.000 H
  H3a 0.7775 0.7837 0.5308 0.0865 Uiso calc C3 0.800 H
  H3b 0.8353 0.9353 0.5327 0.0865 Uiso calc C3 0.800 H
  H4a 0.9294 0.7930 0.4851 0.0750 Uiso calc C4 0.800 H
  H4b 0.8744 0.9315 0.4667 0.0750 Uiso calc C4 0.800 H
  H6 0.9108 0.6487 0.4274 0.0696 Uiso calc C6 1.000 H
  H8 0.5801 0.5860 0.3813 0.0726 Uiso calc C8 1.000 H
  H9 0.4996 0.7394 0.4271 0.0739 Uiso calc C9 1.000 H
  H12a 0.6882 0.5096 0.3334 0.0706 Uiso calc C12 1.000 H
  H12b 0.6970 0.3785 0.3617 0.0706 Uiso calc C12 1.000 H
  H13a 0.8877 0.3303 0.3357 0.0814 Uiso calc C13 1.000 H
  H13b 0.8687 0.4544 0.3054 0.0814 Uiso calc C13 1.000 H
  H14a 0.7151 0.2239 0.3085 0.0854 Uiso calc C14 1.000 H
  H14b 0.8290 0.2310 0.2799 0.0854 Uiso calc C14 1.000 H
  H15a 0.7422 0.4145 0.2475 0.0799 Uiso calc C15 1.000 H
  H15b 0.6282 0.4066 0.2760 0.0799 Uiso calc C15 1.000 H
  H21 0.7702 0.3840 0.1859 0.0642 Uiso calc C21 1.000 H
  H22a 0.8332 0.1158 0.1617 0.0744 Uiso calc C22 1.000 H
  H22b 0.8913 0.1963 0.1979 0.0744 Uiso calc C22 1.000 H
  H23a 1.0138 0.2073 0.1423 0.0860 Uiso calc C23 1.000 H
  H23b 0.9742 0.3577 0.1571 0.0860 Uiso calc C23 1.000 H
  H24a 0.8720 0.2135 0.0940 0.0939 Uiso calc C24 1.000 H
  H24b 0.9537 0.3495 0.0908 0.0939 Uiso calc C24 1.000 H
  H25a 0.7487 0.4015 0.0841 0.0912 Uiso calc C25 1.000 H
  H25b 0.8067 0.4792 0.1208 0.0912 Uiso calc C25 1.000 H
  H26a 0.6244 0.3868 0.1392 0.0771 Uiso calc C26 1.000 H
  H26b 0.6652 0.2369 0.1244 0.0771 Uiso calc C26 1.000 H
  H3Aa 0.8547 0.9789 0.5228 0.0756 Uiso calc C3A 0.200 H
  H3Ab 0.8267 1.0035 0.4776 0.0756 Uiso calc C3A 0.200 H
  H4Aa 0.8248 0.7417 0.5132 0.0612 Uiso calc C4A 0.200 H
  H4Ab 0.9348 0.7983 0.4876 0.0612 Uiso calc C4 0.200 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 0.0778(7) 0.1194(7) 0.0828(8) 0.0330(6) -0.0203(7) -0.0503(7) O
  O11 0.0545(5) 0.0722(5) 0.0604(7) -0.0049(5) 0.0039(6) -0.0181(5) O
  N1 0.0517(6) 0.0644(6) 0.0577(8) 0.0068(6) -0.0049(6) -0.0103(6) N
  N17 0.0683(8) 0.0733(7) 0.0730(10)
  -0.0095(6) 0.0178(7) -0.0015(7) N
  N18 0.0607(7) 0.0710(7) 0.0850(10)
  -0.0152(6) 0.0123(7) -0.0077(7) N
  N19 0.0592(7) 0.0631(6) 0.0730(10)
  -0.0180(6) 0.0046(7) -0.0137(7) N
  N20 0.0460(6) 0.0473(5) 0.0551(8) -0.0074(5) 0.0014(6) -0.0083(6) N
  C2 0.0646(9) 0.0846(9) 0.0600(10)
  0.0153(8) -0.0120(9) -0.0186(9) C
  C3 0.0630(10)
  0.0840(10)
  0.0530(10)
  0.0150(10)
  -0.0100(10)
  -0.0160(10)
  C
  C4 0.0550(10)
  0.0700(10)
  0.0490(10)
  -0.0014(9) -0.0030(10)
  -0.0020(10)
  C
  C5 0.0475(8) 0.0570(7) 0.0479(9) -0.0016(6) -0.0027(7) -0.0013(7) C
  C6 0.0465(8) 0.0612(7) 0.0530(10)
  -0.0012(7) -0.0005(7) -0.0015(8) C
  C7 0.0524(8) 0.0509(6) 0.0478(9) -0.0037(7) 0.0034(7) -0.0004(7) C
  C8 0.0527(8) 0.0609(7) 0.0540(10)
  -0.0059(7) -0.0036(8) -0.0052(8) C
  C9 0.0467(7) 0.0665(8) 0.0570(10)
  -0.0007(7) -0.0038(7) -0.0043(8) C
  C10 0.0521(7) 0.0499(7) 0.0471(9) 0.0015(6) -0.0004(7)  0.0000(7) C
  C12 0.0570(8) 0.0522(7) 0.0540(10)
  -0.0066(7) -0.0021(8) -0.0060(7) C
  C13 0.0605(9) 0.0662(8) 0.0610(10)
  0.0043(7) -0.0013(8) -0.0092(8) C
  C14 0.0700(9) 0.0594(8) 0.0680(10)
  0.0130(7) -0.0044(9) -0.0144(8) C
  C15 0.0770(10)
  0.0557(7) 0.0520(10)
  0.0025(7) 0.0012(9) -0.0059(8) C
  C16 0.0530(8) 0.0512(6) 0.0530(10)
  0.0029(6) 0.0045(8) -0.0032(7) C
  C21 0.0491(7) 0.0470(7) 0.0521(9) -0.0074(6) 0.0015(7) -0.0056(7) C
  C22 0.0474(7) 0.0674(8) 0.0570(10)
  0.0006(7) -0.0066(8) 0.0018(8) C
  C23 0.0514(8) 0.0773(9) 0.0700(10)
  -0.0020(8) 0.0075(8) -0.0056(9) C
  C24 0.0770(10)
  0.0784(9) 0.0610(10)
  -0.0002(9) 0.0131(9) -0.0018(9) C
  C25 0.0830(10)
  0.0681(8) 0.0590(10)
  0.0008(8) 0.0018(9) 0.0064(9) C
  C26 0.0595(8) 0.0566(7) 0.0620(10)
  0.0058(7) -0.0051(8) 0.0015(8) C
  C3A 0.0543 0.068(4) 0.052(5) 0.004(3) -0.008(4) 0.008(4) C
  C4A 0.0480 0.063(4) 0.030(4) -0.013(3) -0.007(3) 0.016(3) 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 . . 1.238(2) ?
  O11 C7 . . 1.374(2) ?
  O11 C12 . . 1.428(2) ?
  N1 C2 . . 1.332(2) ?
  N1 C10 . . 1.416(2) ?
  N1 H1 . . 0.950 ?
  N17 N18 . . 1.357(2) ?
  N17 C16 . . 1.325(2) ?
  N18 N19 . . 1.290(2) ?
  N19 N20 . . 1.355(2) ?
  N20 C16 . . 1.336(2) ?
  N20 C21 . . 1.475(2) ?
  C2 C3 . . 1.503(3) ?
  C2 C3A . . 1.645 ?
  C3 C4 . . 1.533(4) ?
  C3 H3a . . 1.000 ?
  C3 H3b . . 1.000 ?
  C4 C5 . . 1.497(3) ?
  C4 H4a . . 1.000 ?
  C4 H4b . . 1.000 ?
  C5 C6 . . 1.381(2) ?
  C5 C10 . . 1.391(2) ?
  C5 C4A . . 1.606 ?
  C6 C7 . . 1.387(2) ?
  C6 H6 . . 1.000 ?
  C7 C8 . . 1.381(2) ?
  C8 C9 . . 1.388(2) ?
  C8 H8 . . 1.000 ?
  C9 C10 . . 1.378(2) ?
  C9 H9 . . 1.000 ?
  C12 C13 . . 1.502(2) ?
  C12 H12a . . 1.000 ?
  C12 H12b . . 1.000 ?
  C13 C14 . . 1.519(2) ?
  C13 H13a . . 1.000 ?
  C13 H13b . . 1.000 ?
  C14 C15 . . 1.507(2) ?
  C14 H14a . . 1.000 ?
  C14 H14b . . 1.000 ?
  C15 C16 . . 1.482(2) ?
  C15 H15a . . 1.000 ?
  C15 H15b . . 1.000 ?
  C21 C22 . . 1.514(2) ?
  C21 C26 . . 1.514(2) ?
  C21 H21 . . 1.000 ?
  C22 C23 . . 1.514(2) ?
  C22 H22a . . 1.000 ?
  C22 H22b . . 1.000 ?
  C23 C24 . . 1.511(3) ?
  C23 H23a . . 1.000 ?
  C23 H23b . . 1.000 ?
  C24 C25 . . 1.519(2) ?
  C24 H24a . . 1.000 ?
  C24 H24b . . 1.000 ?
  C25 C26 . . 1.517(2) ?
  C25 H25a . . 1.000 ?
  C25 H25b . . 1.000 ?
  C26 H26a . . 1.000 ?
  C26 H26b . . 1.000 ?
  C3A C4A . . 1.4702 ?
  C3A H3Aa . . 1.0000 ?
  C3A H3Ab . . 1.0000 ?
  C4A H4Aa . . 1.0000 ?
  C4A H4Ab . . 1.0000 ?