#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/30/01/2300125.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_2300125 loop_ _publ_author_name 'Llin\`as, Antonio' 'Box, Karl J.' 'Burley, Jonathan C.' 'Glen, Robert C.' 'Goodman, Jonathan M.' _publ_section_title ; A new method for the reproducible generation of polymorphs: two forms of sulindac with very different solubilities ; _journal_issue 2 _journal_name_full 'Journal of Applied Crystallography' _journal_page_first 379 _journal_page_last 381 _journal_volume 40 _journal_year 2007 _chemical_formula_moiety 'C20 H17 F1 O3 S1' _chemical_formula_structural 'C20 H17 F1 O3 S1' _chemical_formula_sum 'C20 H17 F O3 S' _chemical_formula_weight 356.41 _chemical_name_common sulindac _chemical_name_systematic ; 2-[6-fluoro-2-methyl-3- [(4-methylsulfinylphenyl)methylidene]inden-1-yl]- acetic acid ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90.0 _cell_angle_beta 106.0111(29) _cell_angle_gamma 90.0 _cell_formula_units_Z 4 _cell_length_a 12.68581(34) _cell_length_b 8.18939(20) _cell_length_c 17.7934(5) _cell_measurement_temperature 293 _cell_volume 1776.83(9) _computing_structure_refinement GSAS _computing_structure_solution 'DASH, GSAS (see text for citations)' _diffrn_ambient_temperature 293 _diffrn_detector 'Linear PSD' _diffrn_detector_type Stoe _diffrn_measurement_device_type 'Stoe Stadi-P' _diffrn_radiation_monochromator 'Ge (111)' _diffrn_radiation_polarisn_ratio 2.0 _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Co K\a' _diffrn_radiation_wavelength 1.78892 _diffrn_source 'Short-focus sealed ceramic tube' _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 1.00000 _exptl_absorpt_process_details ; GSAS Absorption/surface roughness correction: function number 0 No correction is applied. ; _exptl_crystal_density_diffrn 1.332 _exptl_crystal_F_000 744 _pd_calc_method 'Rietveld Refinement' _pd_char_colour yellow _pd_instr_location ; University Chemical Laboratory Lensfield Road Cambridge CB2 1EW UK ; _pd_meas_2theta_range_inc 0.01 _pd_meas_2theta_range_max 69.99 _pd_meas_2theta_range_min 2.0 _pd_meas_number_of_points 6800 _pd_meas_scan_method step _pd_phase_name SULINDAC_FORM_II_P21_C_RIETVELD _pd_proc_2theta_range_inc 0.01 _pd_proc_2theta_range_max 70.11629 _pd_proc_2theta_range_min 2.12629 _pd_proc_info_datetime 2007-03-07T18:41:29 _pd_proc_info_excluded_regions ' ?' _pd_proc_ls_background_function ; GSAS Background function number 1 with 15 terms. Shifted Chebyshev function of 1st kind 1: 725.334 2: -363.062 3: -69.4872 4: 119.798 5: -10.2295 6: -70.0540 7: 33.7373 8: 39.3149 9: -45.5570 10: 3.81882 11: 29.1700 12: -21.7529 13: -10.9817 14: 16.8347 15: -8.63052 ; _pd_proc_ls_peak_cutoff 0.00100 _pd_proc_ls_profile_function ; CW Profile function number 3 with 19 terms Pseudovoigt profile coefficients as parameterized in P. Thompson, D.E. Cox & J.B. Hastings (1987). J. Appl. Cryst.,20,79-83. Asymmetry correction of L.W. Finger, D.E. Cox & A. P. Jephcoat (1994). J. Appl. Cryst.,27,892-900. Peak tails are ignored where the intensity is below 0.0010 times the peak Aniso. broadening axis 0.0 0.0 1.0 ; _pd_proc_ls_prof_R_factor 0.0381 _pd_proc_ls_prof_wR_expected 0.0310 _pd_proc_ls_prof_wR_factor 0.0505 _pd_proc_number_of_points 6800 _pd_spec_mounting ' ?' _refine_ls_goodness_of_fit_all 1.67 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 150 _refine_ls_number_restraints 145 _refine_ls_R_Fsqd_factor 0.07490 _refine_ls_shift/su_max 0.03 _refine_ls_shift/su_mean 0.01 _reflns_d_resolution_high 1.560 _reflns_d_resolution_low 12.194 _reflns_limit_h_max 9 _reflns_limit_h_min 0 _reflns_limit_k_max 6 _reflns_limit_k_min 0 _reflns_limit_l_max 12 _reflns_limit_l_min -13 _reflns_number_total 494 _[local]_cod_data_source_file kk5012.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_geom_bond_publ_flag' value 'N' changed to 'n' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (98 times). '_geom_angle_publ_flag' value 'N' changed to 'n' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (71 time). Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_geom_bond_publ_flag' value 'N' changed to 'n' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (98 times). '_geom_angle_publ_flag' value 'N' changed to 'n' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (71 time). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1776.83(6) _cod_database_code 2300125 #BEGIN Tags that were not found in dictionaries: _gsas_exptl_extinct_corr_t_min 1.00000 _gsas_exptl_extinct_corr_t_max 1.00000 #END Tags that were not found in dictionaries loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +x,+y,+z 2 -x,+y+1/2,-z+1/2 -1 -x,-y,-z -2 +x,-y+1/2,+z+1/2 loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_U_iso_or_equiv _atom_site_symmetry_multiplicity S S1 -0.5029(4) 0.0558(8) -0.37808(29) 1.0 Uiso 0.1966(20) 4 F F1 0.0418(6) -0.3523(10) 0.0918(4) 1.0 Uiso 0.1966(20) 4 O O1 0.3937(8) 0.1517(9) -0.0136(6) 1.0 Uiso 0.1966(20) 4 H H17 0.396(5) 0.1028(17) 0.1134(13) 1.0 Uiso 0.1966(20) 4 O O2 0.3906(9) 0.0020(11) 0.0898(4) 1.0 Uiso 0.1966(20) 4 O O3 -0.5407(11) 0.2059(8) -0.3439(8) 1.0 Uiso 0.1966(20) 4 C C1 0.0519(4) -0.0399(16) -0.1829(5) 1.0 Uiso 0.1966(20) 4 C C2 0.1712(4) -0.0334(14) -0.1646(4) 1.0 Uiso 0.1966(20) 4 C C3 0.2157(4) -0.0983(13) -0.0930(4) 1.0 Uiso 0.1966(20) 4 C C4 0.1340(4) -0.2304(16) 0.0104(4) 1.0 Uiso 0.1966(20) 4 H H1 0.2011(5) -0.257(4) 0.0453(12) 1.0 Uiso 0.1966(20) 4 C C5 0.0332(5) -0.2680(16) 0.0240(4) 1.0 Uiso 0.1966(20) 4 C C6 -0.0668(4) -0.2488(16) -0.0271(5) 1.0 Uiso 0.1966(20) 4 H H2 -0.1308(5) -0.271(4) -0.0133(9) 1.0 Uiso 0.1966(20) 4 C C7 -0.0685(4) -0.1733(16) -0.0992(5) 1.0 Uiso 0.1966(20) 4 H H3 -0.1357(5) -0.149(4) -0.1344(12) 1.0 Uiso 0.1966(20) 4 C C8 0.0268(4) -0.1160(14) -0.1144(4) 1.0 Uiso 0.1966(20) 4 C C9 0.1290(4) -0.1587(16) -0.0626(5) 1.0 Uiso 0.1966(20) 4 C C10 -0.0117(4) 0.0311(11) -0.2464(4) 1.0 Uiso 0.1966(20) 4 H H4 0.0271(6) 0.0673(33) -0.2806(8) 1.0 Uiso 0.1966(20) 4 C C11 -0.1301(4) 0.0322(14) -0.28089(35) 1.0 Uiso 0.1966(20) 4 C C12 -0.1840(5) -0.0189(23) -0.3563(5) 1.0 Uiso 0.1966(20) 4 H H5 -0.1427(8) -0.053(5) -0.3893(8) 1.0 Uiso 0.1966(20) 4 C C13 -0.2962(5) -0.0197(19) -0.3837(4) 1.0 Uiso 0.1966(20) 4 H H6 -0.3293(8) -0.054(5) -0.4346(9) 1.0 Uiso 0.1966(20) 4 C C14 -0.3599(4) 0.0376(16) -0.33845(34) 1.0 Uiso 0.1966(20) 4 C C15 -0.3099(5) 0.0768(16) -0.25820(35) 1.0 Uiso 0.1966(20) 4 H H7 -0.3516(9) 0.121(4) -0.2278(6) 1.0 Uiso 0.1966(20) 4 C C16 -0.1984(5) 0.0739(19) -0.2312(4) 1.0 Uiso 0.1966(20) 4 H H8 -0.1652(7) 0.107(5) -0.1802(8) 1.0 Uiso 0.1966(20) 4 C C17 0.2317(7) 0.0649(12) -0.2097(5) 1.0 Uiso 0.1966(20) 4 H H9 0.187(5) 0.078(14) -0.2625(23) 1.0 Uiso 0.1966(20) 4 H H10 0.249(9) 0.170(8) -0.186(7) 1.0 Uiso 0.1966(20) 4 H H11 0.298(6) 0.010(7) -0.210(9) 1.0 Uiso 0.1966(20) 4 C C18 0.3338(4) -0.1076(10) -0.0486(4) 1.0 Uiso 0.1966(20) 4 H H12 0.3480(10) -0.2121(10) -0.0221(7) 1.0 Uiso 0.1966(20) 4 H H13 0.3785(7) -0.0986(19) -0.0848(6) 1.0 Uiso 0.1966(20) 4 C C19 0.3655(8) 0.0286(8) 0.0122(4) 1.0 Uiso 0.1966(20) 4 C C20 -0.5445(9) -0.1001(10) -0.3369(7) 1.0 Uiso 0.1966(20) 4 H H14 -0.499(6) -0.1933(20) -0.339(9) 1.0 Uiso 0.1966(20) 4 H H15 -0.539(11) -0.075(8) -0.2833(26) 1.0 Uiso 0.1966(20) 4 H H16 -0.619(4) -0.125(11) -0.364(5) 1.0 Uiso 0.1966(20) 4 loop_ _atom_type_symbol _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source S 4.0 0.000 0.000 6.90530 1.46790 5.20340 22.2151 1.43790 0.25360 1.58630 56.1720 0.86690 International_Tables_Vol_C F 4.0 0.000 0.000 3.53920 10.2825 2.64120 4.29440 1.51700 0.26150 1.02430 26.1476 0.27760 International_Tables_Vol_C O 12.0 0.000 0.000 3.04850 13.2771 2.28680 5.70110 1.54630 0.32390 0.86700 32.9089 0.25080 International_Tables_Vol_C H 68.0 0.000 0.000 0.49300 10.5109 0.32291 26.1257 0.14019 3.14236 0.04081 57.7997 0.00304 International_Tables_Vol_C C 80.0 0.000 0.000 2.31000 20.8439 1.02000 10.2075 1.58860 0.56870 0.86500 51.6512 0.21560 International_Tables_Vol_C loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H17 O2 C19 106.8(14) 1_555 . 1_555 n C2 C1 C8 106.08(23) 1_555 . 1_555 n C2 C1 C10 121.52(24) 1_555 . 1_555 n C8 C1 C10 131.9(4) 1_555 . 1_555 n C1 C2 C3 109.50(27) 1_555 . 1_555 n C1 C2 C17 123.8(4) 1_555 . 1_555 n C3 C2 C17 125.22(29) 1_555 . 1_555 n C2 C3 C9 108.97(24) 1_555 . 1_555 n C2 C3 C18 128.11(28) 1_555 . 1_555 n C9 C3 C18 122.92(28) 1_555 . 1_555 n H1 C4 C5 122.90(33) 1_555 . 1_555 n H1 C4 C9 120.9(5) 1_555 . 1_555 n C5 C4 C9 116.04(25) 1_555 . 1_555 n F1 C5 C4 114.1(4) 1_555 . 1_555 n F1 C5 C6 118.92(28) 1_555 . 1_555 n C4 C5 C6 126.27(26) 1_555 . 1_555 n C5 C6 H2 121.8(4) 1_555 . 1_555 n C5 C6 C7 115.84(24) 1_555 . 1_555 n H2 C6 C7 121.9(5) 1_555 . 1_555 n C6 C7 H3 118.9(5) 1_555 . 1_555 n C6 C7 C8 121.67(24) 1_555 . 1_555 n H3 C7 C8 118.88(32) 1_555 . 1_555 n C1 C8 C7 134.22(27) 1_555 . 1_555 n C1 C8 C9 105.98(25) 1_555 . 1_555 n C7 C8 C9 118.72(29) 1_555 . 1_555 n C3 C9 C4 130.01(26) 1_555 . 1_555 n C3 C9 C8 109.17(25) 1_555 . 1_555 n C4 C9 C8 120.32(32) 1_555 . 1_555 n C1 C10 H4 113.0(5) 1_555 . 1_555 n C1 C10 C11 132.37(32) 1_555 . 1_555 n H4 C10 C11 113.08(33) 1_555 . 1_555 n C10 C11 C12 125.36(29) 1_555 . 1_555 n C10 C11 C16 117.93(28) 1_555 . 1_555 n C12 C11 C16 116.41(29) 1_555 . 1_555 n C11 C12 H5 119.0(5) 1_555 . 1_555 n C11 C12 C13 122.01(25) 1_555 . 1_555 n H5 C12 C13 119.0(4) 1_555 . 1_555 n C12 C13 H6 119.5(5) 1_555 . 1_555 n C12 C13 C14 120.73(28) 1_555 . 1_555 n H6 C13 C14 119.6(4) 1_555 . 1_555 n C13 C14 C15 119.52(23) 1_555 . 1_555 n C14 C15 H7 120.15(34) 1_555 . 1_555 n C14 C15 C16 118.66(27) 1_555 . 1_555 n H7 C15 C16 120.3(5) 1_555 . 1_555 n C11 C16 C15 121.97(25) 1_555 . 1_555 n C11 C16 H8 118.8(5) 1_555 . 1_555 n C15 C16 H8 119.07(32) 1_555 . 1_555 n C2 C17 H9 109.5(4) 1_555 . 1_555 n C2 C17 H10 109.4(31) 1_555 . 1_555 n C2 C17 H11 109.5(19) 1_555 . 1_555 n H9 C17 H10 109.4(17) 1_555 . 1_555 n H9 C17 H11 109.4(16) 1_555 . 1_555 n H10 C17 H11 109.5(13) 1_555 . 1_555 n H10 H9 H11 60.0(5) 1_555 . 1_555 n H9 H10 H11 60.0(12) 1_555 . 1_555 n H9 H11 H10 60.0(8) 1_555 . 1_555 n C3 C18 H12 109.1(4) 1_555 . 1_555 n C3 C18 H13 109.3(4) 1_555 . 1_555 n C3 C18 C19 111.59(32) 1_555 . 1_555 n H12 C18 H13 109.0(4) 1_555 . 1_555 n H12 C18 C19 108.8(4) 1_555 . 1_555 n H13 C18 C19 109.1(4) 1_555 . 1_555 n O1 C19 O2 121.0(5) 1_555 . 1_555 n O1 C19 C18 112.9(4) 1_555 . 1_555 n O2 C19 C18 123.4(4) 1_555 . 1_555 n H14 C20 H15 109.5(12) 1_555 . 1_555 n H14 C20 H16 109.3(12) 1_555 . 1_555 n H15 C20 H16 109.5(4) 1_555 . 1_555 n H15 H14 H16 60.1(5) 1_555 . 1_555 n H14 H15 H16 59.90(31) 1_555 . 1_555 n H14 H16 H15 60.04(32) 1_555 . 1_555 n loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.5071(17) . 1_555 n F1 C5 1.3688(16) . 1_555 n O1 C19 1.2020(16) . 1_555 n H17 O2 0.9202(17) . 1_555 n O2 H17 0.9202(17) . 1_555 n O2 C19 1.3473(16) . 1_555 n O3 S1 1.5071(17) . 1_555 n C1 C2 1.4593(16) . 1_555 n C1 C8 1.4797(16) . 1_555 n C1 C10 1.3278(16) . 1_555 n C2 C1 1.4593(16) . 1_555 n C2 C3 1.3513(16) . 1_555 n C2 C17 1.4896(17) . 1_555 n C3 C2 1.3513(16) . 1_555 n C3 C9 1.4418(16) . 1_555 n C3 C18 1.4904(16) . 1_555 n C4 H1 0.9301(17) . 1_555 n C4 C5 1.4001(16) . 1_555 n C4 C9 1.4099(16) . 1_555 n H1 C4 0.9301(17) . 1_555 n C5 F1 1.3688(16) . 1_555 n C5 C4 1.4001(16) . 1_555 n C5 C6 1.3500(16) . 1_555 n C6 C5 1.3500(16) . 1_555 n C6 H2 0.9298(17) . 1_555 n C6 C7 1.4201(16) . 1_555 n H2 C6 0.9298(17) . 1_555 n C7 C6 1.4201(16) . 1_555 n C7 H3 0.9301(17) . 1_555 n C7 C8 1.3908(16) . 1_555 n H3 C7 0.9301(17) . 1_555 n C8 C1 1.4797(16) . 1_555 n C8 C7 1.3908(16) . 1_555 n C8 C9 1.4109(16) . 1_555 n C9 C3 1.4418(16) . 1_555 n C9 C4 1.4099(16) . 1_555 n C9 C8 1.4109(16) . 1_555 n C10 C1 1.3278(16) . 1_555 n C10 H4 0.9297(17) . 1_555 n C10 C11 1.4583(16) . 1_555 n H4 C10 0.9297(17) . 1_555 n C11 C10 1.4583(16) . 1_555 n C11 C12 1.3918(16) . 1_555 n C11 C16 1.4392(16) . 1_555 n C12 C11 1.3918(16) . 1_555 n C12 H5 0.9302(17) . 1_555 n C12 C13 1.3715(16) . 1_555 n H5 C12 0.9302(17) . 1_555 n C13 C12 1.3715(16) . 1_555 n C13 H6 0.9302(17) . 1_555 n C13 C14 1.3708(16) . 1_555 n H6 C13 0.9302(17) . 1_555 n C14 C13 1.3708(16) . 1_555 n C14 C15 1.4300(16) . 1_555 n C15 C14 1.4300(16) . 1_555 n C15 H7 0.9300(17) . 1_555 n C15 C16 1.3623(16) . 1_555 n H7 C15 0.9300(17) . 1_555 n C16 C11 1.4392(16) . 1_555 n C16 C15 1.3623(16) . 1_555 n C16 H8 0.9299(17) . 1_555 n H8 C16 0.9299(17) . 1_555 n C17 C2 1.4896(17) . 1_555 n C17 H9 0.9602(17) . 1_555 n C17 H10 0.9601(17) . 1_555 n C17 H11 0.9599(17) . 1_555 n H9 C17 0.9602(17) . 1_555 n H9 H10 1.568(17) . 1_555 n H9 H11 1.567(15) . 1_555 n H10 C17 0.9601(17) . 1_555 n H10 H9 1.568(17) . 1_555 n H10 H11 1.568(13) . 1_555 n H11 C17 0.9599(17) . 1_555 n H11 H9 1.567(15) . 1_555 n H11 H10 1.568(13) . 1_555 n C18 C3 1.4904(16) . 1_555 n C18 H12 0.9702(17) . 1_555 n C18 H13 0.9697(17) . 1_555 n C18 C19 1.5284(16) . 1_555 n H12 C18 0.9702(17) . 1_555 n H12 H13 1.579(4) . 1_555 n H13 C18 0.9697(17) . 1_555 n H13 H12 1.579(4) . 1_555 n C19 O1 1.2020(16) . 1_555 n C19 O2 1.3473(16) . 1_555 n C19 C18 1.5284(16) . 1_555 n C20 H14 0.9600(17) . 1_555 n C20 H15 0.9601(17) . 1_555 n C20 H16 0.9602(17) . 1_555 n H14 C20 0.9600(17) . 1_555 n H14 H15 1.568(12) . 1_555 n H14 H16 1.566(12) . 1_555 n H15 C20 0.9601(17) . 1_555 n H15 H14 1.568(12) . 1_555 n H15 H16 1.569(4) . 1_555 n H16 C20 0.9602(17) . 1_555 n H16 H14 1.566(12) . 1_555 n H16 H15 1.569(4) . 1_555 n