#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/28/2012867.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2012867 loop_ _publ_author_name 'Whittall, Linda B.' 'Whittle, Robert R.' 'Stowell, Grayson W.' _publ_section_title ; Polymorphic forms of cilostazol ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o525 _journal_page_last o527 _journal_paper_doi 10.1107/S0108270102012544 _journal_volume 58 _journal_year 2002 _chemical_formula_moiety 'C20 H27 N5 O2' _chemical_formula_sum 'C20 H27 N5 O2' _chemical_formula_weight 369.47 _chemical_melting_point 419 _chemical_name_common Cilostazol _chemical_name_systematic ; 6-[4-(1-Cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydroquinolin-2(1H)-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90 _cell_angle_beta 94.0700(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.1480(10) _cell_length_b 10.7390(10) _cell_length_c 35.2790(10) _cell_measurement_reflns_used 3878 _cell_measurement_temperature 294 _cell_measurement_theta_max 27.49 _cell_measurement_theta_min 1.36 _cell_volume 1945.5(4) _computing_cell_refinement 'KappaCCD Server Software' _computing_data_collection 'KappaCCD Server Software (Nonius, 1997)' _computing_data_reduction 'DENZO and SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'CIFGEN in OpenMolEN' _computing_structure_refinement 'LSFM in OpenMolEN (Nonius, 1997)' _computing_structure_solution 'SIR (Burla et al., 1989)' _diffrn_ambient_temperature 294 _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.963 _diffrn_measured_fraction_theta_max 0.963 _diffrn_measurement_device 'Nonius KappaCCD area-detector' _diffrn_measurement_device_type '95mm CCD camera on \k-goniometer' _diffrn_measurement_method CCD _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_av_sigmaI/netI 0.500 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_number 4572 _diffrn_reflns_theta_full 27.52 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_min 2.5 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.26 _exptl_crystal_density_meas ? _exptl_crystal_density_method none _exptl_crystal_description plate _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.13 _refine_diff_density_min -0.12 _refine_ls_extinction_coef '3.7536 \\times 10^-06^' _refine_ls_extinction_expression ; eq. 22, p. 292 in Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291-294. Copenhagen: Munksgaard. ; _refine_ls_extinction_method 'isotropic (Zachariasen, 1963)' _refine_ls_goodness_of_fit_all 4.189 _refine_ls_goodness_of_fit_ref 1.621 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 245 _refine_ls_number_reflns 2223 _refine_ls_number_restraints 108 _refine_ls_R_factor_all 0.084 _refine_ls_R_factor_gt 0.043 _refine_ls_shift/esd_mean 0.000 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 4Fo^2^/[\s^2^(Fo^2^) + 0.0004Fo^4^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.110 _refine_ls_wR_factor_ref 0.041 _reflns_number_gt 2223 _reflns_number_total 4343 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fg1656.cif _cod_data_source_block IC _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 1945.3(6) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2012867 _cod_database_fobs_code 2012867 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 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_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H H 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N N 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O O 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C7 O11 C12 118.30(10) C2 N1 C10 124.1(2) C2 N1 H1 118.0 C10 N1 H1 118.0 N18 N17 C16 106.2(2) N17 N18 N19 110.8(2) N18 N19 N20 106.1(2) N19 N20 C16 108.6(2) N19 N20 C21 119.4(2) C16 N20 C21 132.0(2) N1 C2 C3 115.3(2) C2 C3 C4 112.0(2) C2 C3 H3a 108.8 C2 C3 H3b 108.8 C4 C3 H3a 108.8 C4 C3 H3b 108.8 H3a C3 H3b 109.5 C3 C4 C5 110.3(2) C3 C4 H4a 109.3 C3 C4 H4b 109.3 C5 C4 H4a 109.2 C5 C4 H4b 109.3 H4a C4 H4b 109.5 C4 C5 C6 123.2(2) C4 C5 C10 118.2(2) C6 C5 C10 118.5(2) C5 C6 C7 121.1(2) C5 C6 H6 119.5 C7 C6 H6 119.5 O11 C7 C6 115.0(2) O11 C7 C8 125.1(2) C6 C7 C8 119.9(2) C7 C8 C9 119.3(2) C7 C8 H8 120.3 C9 C8 H8 120.4 C8 C9 C10 120.7(2) C8 C9 H9 119.7 C10 C9 H9 119.7 N1 C10 C5 119.3(2) N1 C10 C9 120.1(2) C5 C10 C9 120.6(2) O11 C12 C13 106.8(2) O11 C12 H12a 110.2 O11 C12 H12b 110.1 C13 C12 H12a 110.1 C13 C12 H12b 110.1 H12a C12 H12b 109.4 C12 C13 C14 113.1(2) C12 C13 H13a 108.6 C12 C13 H13b 108.6 C14 C13 H13a 108.6 C14 C13 H13b 108.6 H13a C13 H13b 109.4 C13 C14 C15 113.7(2) C13 C14 H14a 108.4 C13 C14 H14b 108.4 C15 C14 H14a 108.4 C15 C14 H14b 108.4 H14a C14 H14b 109.4 C14 C15 C16 112.50(10) C14 C15 H15a 108.7 C14 C15 H15b 108.7 C16 C15 H15a 108.7 C16 C15 H15b 108.7 H15a C15 H15b 109.5 N17 C16 N20 108.3(2) N17 C16 C15 125.6(2) N20 C16 C15 126.0(2) N20 C21 C22 110.40(10) N20 C21 C26 110.4(2) N20 C21 H21 109.2 C22 C21 C26 112.2(2) C22 C21 H21 107.3 C26 C21 H21 107.3 C21 C22 C23 111.4(2) C21 C22 H22a 109.0 C21 C22 H22b 109.0 C23 C22 H22a 109.0 C23 C22 H22b 109.0 H22a C22 H22b 109.5 C22 C23 C24 111.3(2) C22 C23 H23a 109.0 C22 C23 H23b 109.0 C24 C23 H23a 109.0 C24 C23 H23b 109.0 H23a C23 H23b 109.5 C23 C24 C25 110.3(2) C23 C24 H24a 109.3 C23 C24 H24b 109.3 C25 C24 H24a 109.2 C25 C24 H24b 109.3 H24a C24 H24b 109.5 C24 C25 C26 111.6(2) C24 C25 H25a 109.0 C24 C25 H25b 108.9 C26 C25 H25a 108.9 C26 C25 H25b 108.9 H25a C25 H25b 109.5 C21 C26 C25 111.8(2) C21 C26 H26a 108.9 C21 C26 H26b 108.9 C25 C26 H26a 108.9 C25 C26 H26b 108.9 H26a C26 H26b 109.5 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 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C12 O11 C7 C6 -176.90(10) yes C12 O11 C7 C8 4.1(2) ? C7 O11 C12 C13 175.80(10) ? C10 N1 C2 O2 175.40(10) ? C10 N1 C2 C3 -6.2(2) ? C2 N1 C10 C5 -16.2(2) ? C2 N1 C10 C9 165.20(10) ? C16 N17 N18 N19 -0.7(2) ? N18 N17 C16 N20 0.8(2) ? N18 N17 C16 C15 -175.40(10) ? N17 N18 N19 N20 0.4(2) ? N18 N19 N20 C16 0.1(2) ? N18 N19 N20 C21 -178.20(10) ? N19 N20 C16 N17 -0.6(2) ? N19 N20 C16 C15 175.60(10) ? C21 N20 C16 N17 177.50(10) ? C21 N20 C16 C15 -6.4(3) ? N19 N20 C21 C22 -65.2(2) ? N19 N20 C21 C26 59.4(2) ? C16 N20 C21 C22 116.9(2) yes C16 N20 C21 C26 -118.5(2) yes O2 C2 C3 C4 -141.1(2) ? N1 C2 C3 C4 40.4(2) ? C2 C3 C4 C5 -51.6(2) ? C3 C4 C5 C6 -149.80(10) ? C3 C4 C5 C10 31.4(2) ? C4 C5 C6 C7 -179.00(10) ? C10 C5 C6 C7 -0.1(2) ? C4 C5 C10 N1 1.8(2) ? C4 C5 C10 C9 -179.60(10) ? C6 C5 C10 N1 -177.20(10) ? C6 C5 C10 C9 1.4(2) ? C5 C6 C7 O11 179.60(10) ? C5 C6 C7 C8 -1.4(2) ? O11 C7 C8 C9 -179.50(10) ? C6 C7 C8 C9 1.5(2) ? C7 C8 C9 C10 -0.2(2) ? C8 C9 C10 N1 177.30(10) ? C8 C9 C10 C5 -1.3(2) ? O11 C12 C13 C14 -174.70(10) yes C12 C13 C14 C15 178.50(10) yes C13 C14 C15 C16 -64.5(2) yes C14 C15 C16 N17 80.6(2) yes C14 C15 C16 N20 -94.9(2) yes N20 C21 C22 C23 177.00(10) ? C26 C21 C22 C23 53.4(2) ? N20 C21 C26 C25 -176.80(10) ? C22 C21 C26 C25 -53.2(2) ? C21 C22 C23 C24 -55.3(2) ? C22 C23 C24 C25 56.4(2) ? C23 C24 C25 C26 -56.1(2) ? C24 C25 C26 C21 54.7(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 2754