#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/70/2007071.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_2007071 loop_ _publ_author_name 'Chinnakali, Kandasamy' 'Fun, Hoong-Kun' 'Sriraghavan, Kamaraj' 'Ramakrishnan, Vaylakkavoor T.' _publ_section_title ; 8-Acetyl-4-methyl-9-phenylthio-7,8,9,10-tetrahydro-7,8-benzocoumarin ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 367 _journal_page_last 368 _journal_paper_doi 10.1107/S0108270197014522 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C22 H20 O4 S1' _chemical_formula_sum 'C22 H20 O4 S' _chemical_formula_weight 380.44 _chemical_name_systematic ; 8-Acetyl-4-methyl-9-phenylthio-7,8,9,10-tetrahydro-7,8-benzocoumarin ; _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' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 97.636(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.3028(10) _cell_length_b 8.5506(6) _cell_length_c 23.960(2) _cell_measurement_reflns_used 27 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 12.53 _cell_measurement_theta_min 5.15 _cell_volume 1889.0(3) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1994)' _computing_data_reduction XSCANS _computing_molecular_graphics 'SHELXTL/PC. Geometrical calculations PARST (Nardelli, 1983b)' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXTL/PC (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.017 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 5750 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 1.72 _diffrn_standards_decay_% <3 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.196 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular block' _exptl_crystal_F_000 800 _exptl_crystal_size_max 0.84 _exptl_crystal_size_mid 0.68 _exptl_crystal_size_min 0.54 _refine_diff_density_max 0.217 _refine_diff_density_min -0.238 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.048 _refine_ls_goodness_of_fit_obs 1.131 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 324 _refine_ls_number_reflns 4303 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_restrained_S_obs 1.131 _refine_ls_R_factor_all 0.050 _refine_ls_R_factor_obs .040 _refine_ls_shift/esd_max -0.007 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.183P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.116 _refine_ls_wR_factor_obs .111 _reflns_number_observed 3450 _reflns_number_total 4303 _reflns_observed_criterion >2sigma(I) _cod_data_source_file cf1196.cif _cod_data_source_block ksr295 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.183P] where P = (Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.183P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2007071 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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 S .0597(2) .0450(2) .0466(2) -.0148(2) -.0052(2) .0089(2) O1 .0373(5) .0530(6) .0444(5) .0018(4) .0059(4) -.0029(4) C2 .0472(8) .0434(8) .0519(8) -.0060(6) .0004(6) .0036(6) C3 .0601(9) .0527(9) .0463(8) -.0081(8) -.0004(7) -.0030(7) C4 .0669(10) .0425(7) .0419(7) -.0054(7) .0123(7) -.0007(6) C5 .0540(8) .0518(9) .0547(9) .0064(7) .0220(7) -.0063(7) C6 .0405(7) .0512(9) .0652(10) .0066(7) .0190(7) -.0023(7) C7 .0375(7) .0363(6) .0504(8) .0015(6) .0103(6) .0024(6) C8 .0377(6) .0352(6) .0404(7) .0021(5) .0097(5) .0031(5) C9 .0393(7) .0360(6) .0422(7) .0007(5) .0113(5) .0030(5) C10 .0493(7) .0388(7) .0428(7) -.0004(6) .0134(6) .0006(6) O11 .0424(6) .0691(8) .0723(8) -.0010(5) -.0007(5) -.0031(6) C12 .0352(7) .0460(8) .0608(9) .0005(6) .0054(6) .0013(7) C13 .0436(7) .0396(7) .0440(7) -.0040(6) .0015(6) .0050(6) C14 .0434(7) .0386(7) .0372(6) .0002(6) .0050(5) .0029(5) C15 .0369(6) .0473(8) .0385(7) .0056(6) .0060(5) .0005(6) C16 .0863(14) .0772(14) .0499(10) -.0038(13) .0169(10) -.0166(10) C17 .0433(7) .0421(7) .0363(6) -.0022(6) .0073(5) .0034(5) C18 .0614(9) .0389(7) .0440(7) -.0001(7) .0063(7) .0035(6) C19 .0654(10) .0515(9) .0435(8) -.0050(8) .0082(7) -.0086(7) C20 .0562(9) .0671(10) .0396(8) .0042(8) .0013(7) -.0016(7) C21 .0558(9) .0526(9) .0509(8) .0116(7) .0049(7) .0057(7) C22 .0484(8) .0411(7) .0482(8) .0028(6) .0080(6) -.0007(6) O23 .0648(6) .0366(5) .0454(5) -.0069(5) .0091(5) .0015(4) C24 .0559(9) .0417(8) .0579(9) -.0091(7) .0080(7) -.0049(7) O25 .0878(9) .0589(7) .0566(7) -.0084(7) .0029(6) -.0118(6) C26 .129(2) .0400(10) .084(2) -.0104(12) .022(2) .0036(10) 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_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol S .13988(5) .85105(5) .26928(2) .05153(13) Uani d . 1 . S O1 -.12953(10) .90428(13) .08229(4) .0448(2) Uani d . 1 . O C2 -.2285(2) .8586(2) .03700(7) .0481(3) Uani d . 1 . C C3 -.1713(2) .7848(2) -.00928(7) .0537(4) Uani d . 1 . C C4 -.0297(2) .7562(2) -.00938(6) .0500(4) Uani d . 1 . C C5 .2230(2) .7907(2) .04248(7) .0522(4) Uani d . 1 . C C6 .3113(2) .8449(2) .08854(7) .0512(4) Uani d . 1 . C C7 .25424(15) .9151(2) .13361(6) .0410(3) Uani d . 1 . C C8 .10485(14) .9336(2) .13140(5) .0374(3) Uani d . 1 . C C9 .01728(14) .8796(2) .08352(6) .0386(3) Uani d . 1 . C C10 .0716(2) .8067(2) .03864(6) .0430(3) Uani d . 1 . C O11 -.35452(12) .8824(2) .04057(6) .0620(3) Uani d . 1 . O C12 .3562(2) .9678(2) .18408(7) .0474(3) Uani d . 1 . C C13 .2906(2) 1.0847(2) .22068(6) .0428(3) Uani d . 1 . C C14 .1395(2) 1.0370(2) .23224(6) .0397(3) Uani d . 1 . C C15 .0371(2) 1.0160(2) .17727(6) .0408(3) Uani d . 1 . C C16 .0253(3) .6752(3) -.05791(9) .0704(5) Uani d . 1 . C C17 .2648(2) .8727(2) .33140(6) .0404(3) Uani d . 1 . C C18 .2956(2) 1.0143(2) .35898(6) .0482(3) Uani d . 1 . C C19 .3906(2) 1.0177(2) .40888(7) .0534(4) Uani d . 1 . C C20 .4518(2) .8811(2) .43173(7) .0548(4) Uani d . 1 . C C21 .4200(2) .7406(2) .40523(7) .0533(4) Uani d . 1 . C C22 .3276(2) .7358(2) .35458(6) .0457(3) Uani d . 1 . C O23 .27781(12) 1.23133(12) .18957(4) .0488(3) Uani d . 1 . O C24 .2827(2) 1.3641(2) .21984(7) .0518(4) Uani d . 1 . C O25 .2898(2) 1.3660(2) .27043(5) .0684(4) Uani d . 1 . O C26 .2778(4) 1.5042(3) .18256(12) .0836(7) Uani d . 1 . C H3 -.239(2) .758(2) -.0394(8) .063(5) Uiso d . 1 . H H5 .265(2) .746(2) .0125(8) .058(5) Uiso d . 1 . H H6 .420(2) .840(2) .0908(8) .062(5) Uiso d . 1 . H H12A .386(2) .878(2) .2085(8) .056(5) Uiso d . 1 . H H12B .445(2) 1.023(2) .1738(8) .062(5) Uiso d . 1 . H H13 .3552(18) 1.1052(19) .2540(7) .044(4) Uiso d . 1 . H H14 .0985(16) 1.1114(19) .2546(6) .038(4) Uiso d . 1 . H H15B .0040(18) 1.121(2) .1641(7) .047(4) Uiso d . 1 . H H15A -.0502(19) .963(2) .1841(6) .047(4) Uiso d . 1 . H H16A -.049(3) .648(3) -.0843(11) .082(7) Uiso d . 1 . H H16B .095(3) .736(3) -.0727(10) .086(7) Uiso d . 1 . H H16C .074(3) .585(3) -.0465(10) .088(8) Uiso d . 1 . H H18 .253(2) 1.108(2) .3432(8) .060(5) Uiso d . 1 . H H19 .408(2) 1.120(3) .4269(8) .069(6) Uiso d . 1 . H H20 .5160(19) .881(2) .4658(8) .055(5) Uiso d . 1 . H H21 .459(2) .646(2) .4213(9) .070(6) Uiso d . 1 . H H22 .3045(18) .635(2) .3346(7) .050(4) Uiso d . 1 . H H26A .300(4) 1.587(5) .2049(14) .138(12) Uiso d . 1 . H H26B .176(4) 1.516(4) .1677(15) .149(14) Uiso d . 1 . H H26C .335(5) 1.500(5) .1550(17) .179(17) Uiso d . 1 . H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C17 S C14 106.07(7) no C9 O1 C2 121.88(12) ? O11 C2 O1 116.72(14) ? O11 C2 C3 126.34(15) ? O1 C2 C3 116.93(13) ? C4 C3 C2 123.09(15) ? C3 C4 C10 118.59(14) ? C3 C4 C16 121.5(2) ? C10 C4 C16 119.9(2) ? C6 C5 C10 120.65(14) ? C5 C6 C7 121.29(14) ? C8 C7 C6 119.87(14) ? C8 C7 C12 121.08(13) no C6 C7 C12 119.05(13) no C7 C8 C9 117.68(12) ? C7 C8 C15 122.38(12) no C9 C8 C15 119.87(12) no O1 C9 C8 115.83(12) ? O1 C9 C10 120.75(13) ? C8 C9 C10 123.41(13) ? C9 C10 C5 117.07(14) ? C9 C10 C4 118.73(13) ? C5 C10 C4 124.17(14) ? C7 C12 C13 113.89(12) no O23 C13 C12 106.54(12) no O23 C13 C14 107.98(11) no C12 C13 C14 112.44(12) no C13 C14 C15 111.02(11) no C13 C14 S 112.33(10) no C15 C14 S 106.12(10) no C8 C15 C14 114.13(11) no C18 C17 C22 119.60(13) no C18 C17 S 124.09(11) no C22 C17 S 116.19(11) no C19 C18 C17 119.63(15) no C20 C19 C18 120.3(2) no C21 C20 C19 120.33(15) no C20 C21 C22 120.0(2) no C17 C22 C21 120.10(14) no C24 O23 C13 117.17(11) no O25 C24 O23 123.17(15) no O25 C24 C26 125.8(2) no O23 C24 C26 111.0(2) no 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 S C17 . 1.7723(15) no S C14 . 1.8209(14) no O1 C9 . 1.378(2) ? O1 C2 . 1.383(2) ? C2 O11 . 1.204(2) ? C2 C3 . 1.438(2) ? C3 C4 . 1.341(2) ? C4 C10 . 1.452(2) ? C4 C16 . 1.501(2) no C5 C6 . 1.366(2) ? C5 C10 . 1.406(2) ? C6 C7 . 1.400(2) ? C7 C8 . 1.393(2) ? C7 C12 . 1.503(2) no C8 C9 . 1.394(2) ? C8 C15 . 1.512(2) no C9 C10 . 1.395(2) ? C12 C13 . 1.511(2) no C13 O23 . 1.455(2) no C13 C14 . 1.525(2) no C14 C15 . 1.530(2) no C17 C18 . 1.390(2) no C17 C22 . 1.391(2) no C18 C19 . 1.390(2) no C19 C20 . 1.380(2) no C20 C21 . 1.373(2) no C21 C22 . 1.391(2) no O23 C24 . 1.345(2) no C24 O25 . 1.205(2) no C24 C26 . 1.491(3) no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA C6 H6 O11 1_655 1.01(2) 2.58(2) 3.470(2) 147(2) C19 H19 O11 2_555 0.98(2) 2.45(2) 3.378(2) 159(2) 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 C9 O1 C2 O11 178.43(14) ? C9 O1 C2 C3 -0.5(2) ? O11 C2 C3 C4 -177.1(2) ? O1 C2 C3 C4 1.6(2) ? C2 C3 C4 C10 -2.1(2) ? C2 C3 C4 C16 178.4(2) ? C10 C5 C6 C7 1.2(3) ? C5 C6 C7 C8 -1.3(2) ? C5 C6 C7 C12 178.0(2) ? C6 C7 C8 C9 0.3(2) ? C12 C7 C8 C9 -179.04(13) ? C6 C7 C8 C15 -176.70(14) ? C12 C7 C8 C15 4.0(2) yes C2 O1 C9 C8 179.09(12) ? C2 O1 C9 C10 -0.1(2) ? C7 C8 C9 O1 -178.14(12) ? C15 C8 C9 O1 -1.1(2) ? C7 C8 C9 C10 1.0(2) ? C15 C8 C9 C10 178.05(13) ? O1 C9 C10 C5 177.93(13) ? C8 C9 C10 C5 -1.2(2) ? O1 C9 C10 C4 -0.4(2) ? C8 C9 C10 C4 -179.49(13) ? C6 C5 C10 C9 0.1(2) ? C6 C5 C10 C4 178.29(15) ? C3 C4 C10 C9 1.5(2) ? C16 C4 C10 C9 -179.1(2) ? C3 C4 C10 C5 -176.7(2) ? C16 C4 C10 C5 2.8(3) ? C8 C7 C12 C13 -19.1(2) yes C6 C7 C12 C13 161.57(14) ? C7 C12 C13 O23 -72.1(2) ? C7 C12 C13 C14 46.0(2) yes O23 C13 C14 C15 59.58(15) ? C12 C13 C14 C15 -57.7(2) yes O23 C13 C14 S 178.22(9) ? C12 C13 C14 S 60.97(14) ? C17 S C14 C13 55.89(12) ? C17 S C14 C15 177.38(9) ? C7 C8 C15 C14 -15.7(2) yes C9 C8 C15 C14 167.42(12) ? C13 C14 C15 C8 41.5(2) yes S C14 C15 C8 -80.80(13) ? C14 S C17 C18 28.90(15) ? C14 S C17 C22 -154.96(11) ? C22 C17 C18 C19 1.1(2) ? S C17 C18 C19 177.14(12) ? C17 C18 C19 C20 -1.5(2) ? C18 C19 C20 C21 0.4(3) ? C19 C20 C21 C22 1.1(3) ? C18 C17 C22 C21 0.4(2) ? S C17 C22 C21 -175.96(12) ? C20 C21 C22 C17 -1.5(2) ? C12 C13 O23 C24 -152.18(13) ? C14 C13 O23 C24 86.82(15) ? C13 O23 C24 O25 -3.8(2) ? C13 O23 C24 C26 176.4(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139055915