#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/32/2003259.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_2003259 loop_ _publ_author_name 'Blake, A. J.' 'Cadogan, J. I. G.' 'Dijksma, F. J. J.' 'Gould, R. O.' 'MacPherson, A. D.' 'McNab, H.' _publ_section_title ; Methyl 3-[2-(tert-Butylthio)phenyl]propenoate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 509 _journal_page_last 511 _journal_paper_doi 10.1107/S0108270194009777 _journal_volume 51 _journal_year 1995 _chemical_compound_source ; The title compound was made by a Wittig reaction of 2-(t-butylthio)benzalde- hyde with methyl triphenylphosphoranylidenacetate in dichloromethane (MacPherson, 1994; Cadogan, MacPherson & McNab, 1994). Crystals were grown from hexane solution. ; _chemical_formula_moiety 'C14 H18 O2 S' _chemical_formula_sum 'C14 H18 O2 S' _chemical_formula_weight 250.34 _chemical_melting_point 332.5(5) _chemical_name_common 'Methyl 2-(t-Butylthio)cinnamate' _chemical_name_systematic ; Methyl 3-[2-(t-Butylthio)phenyl]propenoate ; _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' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 95.64(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.8813(14) _cell_length_b 15.474(3) _cell_length_c 14.919(6) _cell_measurement_reflns_used 60 _cell_measurement_temperature 150.0(2) _cell_measurement_theta_max 16 _cell_measurement_theta_min 10 _cell_volume 1351.2(7) _computing_cell_refinement 'Stoe DIF4' _computing_data_collection 'Stoe DIF4 (Stoe & Cie, 1988a)' _computing_data_reduction 'Stoe REDU4 (Stoe & Cie, 1988b)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1992)' _computing_structure_refinement 'SHELXL-92 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _diffrn_ambient_temperature 150.0(2) _diffrn_measurement_device 'Stoe Stadi-4 four-circle diffractometer' _diffrn_measurement_method ; \w-2\q scans of variable width using on-line profile-fitting (Clegg, 1981) ; _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 0.0112 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3471 _diffrn_reflns_theta_max 25.06 _diffrn_reflns_theta_min 2.63 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.231 _exptl_crystal_description blocks _exptl_crystal_F_000 536 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.35 _refine_diff_density_max 0.181 _refine_diff_density_min -0.258 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.063 _refine_ls_goodness_of_fit_obs 1.071 _refine_ls_hydrogen_treatment ; H atoms placed in calculated positions, with U~iso~ = 1.2U~eq~ of the carbon atom on which the hydrogen atom is riding ; _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 2366 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.088 _refine_ls_restrained_S_obs 1.071 _refine_ls_R_factor_all 0.0393 _refine_ls_R_factor_obs 0.0295 _refine_ls_shift/esd_max 0.029 _refine_ls_shift/esd_mean 0.005 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.5806P]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0803 _refine_ls_wR_factor_obs 0.0727 _reflns_number_observed 2028 _reflns_number_total 2379 _reflns_observed_criterion >2sigma(I) _cod_data_source_file ha1130.cif _cod_data_source_block butest _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '332-333K' was changed to '332.5(5)' - the average value was taken and precision was estimated. '_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^)+(0.0362P)^2^+0.5806P]' 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^)+(0.0362P)^2^+0.5806P]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2003259 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 C1 0.0297(8) 0.0013(6) 0.0046(6) 0.0230(8) -0.0007(6) 0.0197(7) C2 0.0288(8) 0.0017(6) 0.0051(6) 0.0258(8) -0.0011(6) 0.0201(7) C3 0.0339(9) 0.0092(7) -0.0005(7) 0.0363(9) 0.0002(7) 0.0258(8) C4 0.0508(11) 0.0163(8) 0.0011(8) 0.0337(10) 0.0048(7) 0.0286(9) C5 0.0564(11) 0.0045(8) 0.0071(8) 0.0217(8) 0.0027(7) 0.0300(9) C6 0.0392(9) -0.0012(7) 0.0019(7) 0.0246(8) -0.0003(6) 0.0267(8) C7 0.0312(8) -0.0017(6) 0.0035(6) 0.0203(7) -0.0009(6) 0.0200(7) C8 0.0279(8) -0.0016(6) 0.0042(6) 0.0201(7) -0.0016(6) 0.0247(7) C9 0.0265(8) -0.0010(6) 0.0039(6) 0.0238(8) -0.0048(6) 0.0186(7) O9 0.0337(6) -0.0041(5) -0.0012(5) 0.0241(6) 0.0044(5) 0.0338(6) O10 0.0279(6) -0.0015(5) -0.0058(5) 0.0237(6) 0.0010(5) 0.0344(6) C10 0.0315(9) 0.0033(7) -0.0071(7) 0.0300(9) 0.0013(7) 0.0380(9) S 0.0243(2) -0.0031(2) 0.00459(14) 0.0281(2) -0.0026(2) 0.0214(2) C1B 0.0207(8) -0.0003(6) 0.0028(6) 0.0335(9) -0.0060(6) 0.0217(7) C2B 0.0355(9) 0.0048(8) 0.0012(7) 0.0555(12) -0.0014(8) 0.0215(8) C3B 0.0387(10) -0.0053(8) 0.0090(8) 0.0372(10) -0.0130(8) 0.0403(10) C4B 0.0232(8) 0.0010(8) 0.0066(7) 0.0484(11) -0.0072(8) 0.0361(9) loop_ _atom_site_label _atom_site_occupancy _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_type_symbol C1 1 0.5699(3) 0.53306(10) 0.25586(9) 0.0240(3) Uani d . C C2 1 0.3632(3) 0.50441(10) 0.20951(9) 0.0247(3) Uani d . C C3 1 0.2175(3) 0.56423(11) 0.16317(11) 0.0322(4) Uani d . C H3 1 0.0740(3) 0.54512(11) 0.13354(11) 0.039 Uiso d R H C4 1 0.2770(3) 0.65017(12) 0.15906(11) 0.0379(4) Uani d . C H4 1 0.1749(3) 0.69041(12) 0.12690(11) 0.045 Uiso d R H C5 1 0.4836(3) 0.67828(11) 0.20171(11) 0.0358(4) Uani d . C H5 1 0.5278(3) 0.73774(11) 0.19739(11) 0.043 Uiso d R H C6 1 0.6260(3) 0.62073(10) 0.24976(11) 0.0303(4) Uani d . C H6 1 0.7671(3) 0.64110(10) 0.28035(11) 0.036 Uiso d R H C7 1 0.7185(3) 0.47344(10) 0.31084(9) 0.0238(3) Uani d . C H7 1 0.6635(3) 0.41531(10) 0.31503(9) 0.029 Uiso d R H C8 1 0.9192(3) 0.49057(10) 0.35580(10) 0.0241(3) Uani d . C H8 1 0.9829(3) 0.54762(10) 0.35430(10) 0.029 Uiso d R H C9 1 1.0447(3) 0.42195(10) 0.40793(9) 0.0229(3) Uani d . C O9 1 0.9741(2) 0.35037(7) 0.42082(7) 0.0308(3) Uani d . O O10 1 1.2549(2) 0.44878(7) 0.43987(7) 0.0292(3) Uani d . O C10 1 1.3961(3) 0.38478(11) 0.48858(12) 0.0339(4) Uani d . C H10A 1 1.5414(3) 0.41015(11) 0.50836(12) 0.041 Uiso d R H H10B 1 1.3238(3) 0.36537(11) 0.53992(12) 0.041 Uiso d R H H10C 1 1.4183(3) 0.33655(11) 0.44990(12) 0.041 Uiso d R H S 1 0.27503(6) 0.39442(3) 0.21009(2) 0.02445(12) Uani d . S C1B 1 0.3771(2) 0.34955(10) 0.10608(10) 0.0252(3) Uani d . C C2B 1 0.2647(3) 0.39574(13) 0.02310(11) 0.0376(4) Uani d . C H2B1 1 0.3199(3) 0.37176(13) -0.03002(11) 0.045 Uiso d R H H2B2 1 0.1019(3) 0.38889(13) 0.01994(11) 0.045 Uiso d R H H2B3 1 0.3024(3) 0.45607(13) 0.02716(11) 0.045 Uiso d R H C3B 1 0.2991(3) 0.25586(12) 0.10687(12) 0.0384(4) Uani d . C H3B1 1 0.3451(3) 0.22653(12) 0.05490(12) 0.046 Uiso d R H H3B2 1 0.3664(3) 0.22783(12) 0.16046(12) 0.046 Uiso d R H H3B3 1 0.1357(3) 0.25420(12) 0.10566(12) 0.046 Uiso d R H C4B 1 0.6358(3) 0.35467(13) 0.10938(12) 0.0357(4) Uani d . C H4B1 1 0.6839(3) 0.33097(13) 0.05486(12) 0.043 Uiso d R H H4B2 1 0.6831(3) 0.41395(13) 0.11512(12) 0.043 Uiso d R H H43 1 0.7036(3) 0.32233(13) 0.16003(12) 0.043 Uiso d R H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.001 H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000 O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.006 S S 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.1246 0.123 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 C6 C1 C2 118.04(14) y C3 C2 C1 119.46(15) y C4 C3 C2 121.0(2) y C3 C4 C5 119.9(2) y C6 C5 C4 119.9(2) y C5 C6 C1 121.7(2) y C6 C1 C7 120.96(14) y C2 C1 C7 120.98(14) y C8 C7 C1 127.57(15) y C7 C8 C9 119.91(14) y O9 C9 O10 123.10(14) y O9 C9 C8 125.79(14) y O10 C9 C8 111.11(13) y C9 O10 C10 115.47(12) y C3 C2 S 118.09(12) y C1 C2 S 122.43(12) y C2 S C1B 103.63(7) y C4B C1B C3B 110.55(14) n C4B C1B C2B 110.80(14) n C3B C1B C2B 110.27(14) n C4B C1B S 111.05(11) y C3B C1B S 103.18(11) y C2B C1B S 110.76(11) y loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.409(2) y C2 C3 1.398(2) y C3 C4 1.378(3) y C4 C5 1.385(3) y C5 C6 1.375(2) y C6 C1 1.401(2) y C1 C7 1.465(2) y C7 C8 1.326(2) y C8 C9 1.471(2) y C9 O9 1.205(2) y C9 O10 1.346(2) y O10 C10 1.442(2) y C2 S 1.780(2) y S C1B 1.853(2) y C1B C4B 1.519(2) ? C1B C3B 1.521(2) ? C1B C2B 1.523(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 C6 C1 C2 C3 -3.1(2) ? C7 C1 C2 C3 175.26(13) ? C6 C1 C2 S 178.77(11) ? C7 C1 C2 S -2.9(2) ? C1 C2 C3 C4 2.7(2) ? S C2 C3 C4 -179.10(13) ? C2 C3 C4 C5 -0.3(3) ? C3 C4 C5 C6 -1.5(3) ? C4 C5 C6 C1 1.1(3) ? C2 C1 C6 C5 1.2(2) ? C7 C1 C6 C5 -177.07(15) ? C6 C1 C7 C8 -3.8(2) y C2 C1 C7 C8 177.96(15) y C1 C7 C8 C9 179.88(13) y C7 C8 C9 O9 -6.6(2) y C7 C8 C9 O10 172.76(13) y O9 C9 O10 C10 2.1(2) y C8 C9 O10 C10 -177.26(13) y C3 C2 S C1B 87.08(13) y C1 C2 S C1B -94.72(13) y C2 S C1B C4B 62.00(13) n C2 S C1B C3B -179.54(11) n C2 S C1B C2B -61.56(13) n loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21187423 2 PubChem 101916922