#------------------------------------------------------------------------------ #$Date: 2016-02-14 14:26:36 +0000 (Sun, 14 Feb 2016) $ #$Revision: 176435 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200515.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_2200515 loop_ _publ_author_name 'Meyers, Cal Y.' 'Hua, Duy H.' 'Hou, Yuqing' 'Robinson, Paul D.' _publ_section_title ; 2-Chloro-2-propyl mesityl sulfone ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o587 _journal_page_last o589 _journal_paper_doi 10.1107/S1600536801007528 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C12 H17 Cl1 O2 S1' _chemical_formula_moiety 'C12 H17 Cl1 O2 S1' _chemical_formula_sum 'C12 H17 Cl O2 S' _chemical_formula_weight 260.70 _chemical_melting_point 361.0(10) _chemical_name_systematic ; \a-chloroisopropyl mesityl sulfone ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 99.333(9) _cell_angle_beta 93.671(11) _cell_angle_gamma 66.342(14) _cell_formula_units_Z 2 _cell_length_a 9.237(2) _cell_length_b 9.4592(13) _cell_length_c 8.2079(6) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 12.9 _cell_measurement_theta_min 12.5 _cell_volume 648.19(19) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation,1996) ; _computing_data_reduction 'PROCESS in TEXSAN (Molecular Structure Corporation, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1965) in TEXSAN' _computing_publication_material 'TEXSAN, SHELXL97, and PLATON (Spek, 2000)' _computing_structure_refinement 'LS in TEXSAN and SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Burla et al., 1989)' _diffrn_ambient_temperature 296 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Rigaku AFC-5S' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71069 _diffrn_reflns_av_R_equivalents .012 _diffrn_reflns_av_sigmaI/netI .021 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 2442 _diffrn_reflns_theta_full 25.04 _diffrn_reflns_theta_max 25.04 _diffrn_reflns_theta_min 2.38 _diffrn_standards_decay_% .5 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .439 _exptl_absorpt_correction_T_max .916 _exptl_absorpt_correction_T_min .853 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_meas ? _exptl_crystal_description fragment _exptl_crystal_F_000 276 _exptl_crystal_size_max .41 _exptl_crystal_size_mid .36 _exptl_crystal_size_min .20 _refine_diff_density_max .31 _refine_diff_density_min -.26 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 160 _refine_ls_number_reflns 2286 _refine_ls_number_restraints 10 _refine_ls_restrained_S_all 1.068 _refine_ls_R_factor_all .055 _refine_ls_R_factor_gt .040 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0632P)^2^+0.2754P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .121 _reflns_number_gt 1805 _reflns_number_total 2286 _reflns_threshold_expression I>2\s(I) _cod_data_source_file om6025.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '360-362' was changed to '361.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '360-362' was changed to '361.0(10)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 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 648.23(18) _cod_original_formula_sum 'C12 H17 Cl1 O2 S1' _cod_database_code 2200515 _cod_database_fobs_code 2200515 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl(2) .4552(3) .0802(2) .3168(2) .0771(4) Uani d PD .800(4) A 1 Cl Cl(3) .6037(11) .1583(13) .0750(5) .103(4) Uani d PD .198(4) A 1 Cl S1 .31961(7) .39768(7) .23486(7) .0442(2) Uani d . 1 A . S O1 .2416(2) .4477(2) .3919(2) .0616(5) Uani d . 1 . . O O2 .3671(2) .5059(2) .1729(3) .0648(5) Uani d . 1 . . O C1 .2026(2) .3316(3) .0846(3) .0385(5) Uani d . 1 . . C C2 .0913(3) .2802(3) .1366(3) .0420(5) Uani d . 1 . . C C3 .0099(3) .2220(3) .0152(3) .0499(6) Uani d . 1 . . C C4 .0297(3) .2155(3) -.1512(3) .0521(6) Uani d . 1 . . C C5 .1340(3) .2729(3) -.1966(3) .0522(6) Uani d . 1 . . C C6 .2214(3) .3323(3) -.0846(3) .0453(6) Uani d . 1 . . C C7 .3255(4) .3953(4) -.1576(4) .0708(8) Uani d . 1 . . C C8 .0474(4) .2875(4) .3131(3) .0630(8) Uani d . 1 . . C C9 -.0611(4) .1495(4) -.2777(4) .0785(10) Uani d . 1 . . C C10 .5035(3) .2275(3) .2586(3) .0521(6) Uani d D 1 . . C C11 .6007(3) .2854(4) .3967(4) .0692(9) Uani d . 1 A . C C12 .463(5) .093(3) .302(3) .0544(16) Uiso d PD .199(4) A 2 C C13 .6004(9) .1585(8) .1013(4) .0544(16) Uiso d PD .801(4) A 2 C H3 -.0619 .1856 .0476 .060 Uiso calc R 1 . . H H5 .1464 .2717 -.3084 .063 Uiso calc R 1 . . H H7a .3178 .3793 -.2759 .106 Uiso calc R 1 . . H H7b .4331 .3416 -.1254 .106 Uiso calc R 1 . . H H7c .2915 .5049 -.1180 .106 Uiso calc R 1 . . H H8a -.0251 .2381 .3144 .094 Uiso calc R 1 . . H H8b -.0015 .3946 .3634 .094 Uiso calc R 1 . . H H8c .1409 .2345 .3736 .094 Uiso calc R 1 . . H H9a -.1189 .2258 -.3477 .118 Uiso calc R 1 . . H H9b -.1336 .1233 -.2227 .118 Uiso calc R 1 . . H H9c .0112 .0575 -.3434 .118 Uiso calc R 1 . . H H11a .7006 .2016 .4104 .104 Uiso calc R 1 . . H H11b .5429 .3192 .4988 .104 Uiso calc R 1 . . H H11c .6180 .3709 .3656 .104 Uiso calc R 1 . . H H12a .4069 .0603 .2123 .082 Uiso calc PR .199(4) A 2 H H12b .3993 .1296 .4000 .082 Uiso calc PR .199(4) A 2 H H12c .5595 .0068 .3213 .082 Uiso calc PR .199(4) A 2 H H13a .5397 .1239 .0171 .082 Uiso calc PR .801(4) A 2 H H13b .6952 .0714 .1220 .082 Uiso calc PR .801(4) A 2 H H13c .6274 .2364 .0652 .082 Uiso calc PR .801(4) A 2 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 Cl(2) .0816(8) .0680(7) .0767(8) -.0178(6) -.0056(6) .0313(6) Cl(3) .063(3) .138(6) .062(3) .004(3) .014(3) -.001(3) S1 .0394(3) .0435(3) .0452(4) -.0159(3) -.0008(2) -.0040(2) O1 .0544(10) .0735(12) .0456(10) -.0229(9) .0040(8) -.0175(9) O2 .0606(12) .0513(10) .0883(15) -.0305(9) -.0013(10) .0047(10) C1 .0362(11) .0397(11) .0356(11) -.0120(9) -.0014(9) .0035(9) C2 .0398(12) .0463(12) .0390(12) -.0170(10) .0007(9) .0040(10) C3 .0420(13) .0523(14) .0560(15) -.0217(11) -.0036(11) .0037(12) C4 .0516(14) .0425(13) .0484(14) -.0093(11) -.0148(11) -.0005(11) C5 .0593(16) .0546(14) .0324(12) -.0121(12) -.0037(11) .0075(10) C6 .0444(13) .0484(13) .0386(12) -.0119(11) .0004(10) .0110(10) C7 .074(2) .093(2) .0568(17) -.0374(18) .0061(14) .0286(16) C8 .0650(17) .091(2) .0452(15) -.0442(16) .0091(12) .0049(14) C9 .083(2) .0664(19) .072(2) -.0254(17) -.0313(17) -.0074(16) C10 .0425(13) .0568(15) .0479(14) -.0142(11) -.0077(11) .0010(11) C11 .0453(15) .087(2) .0553(16) -.0161(14) -.0226(12) -.0069(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 -1 0 1 -1 0 1 -2 1 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 C13 C10 C11 110.0(3) yes C11 C10 C12 113.0(13) yes C11 C10 Cl(3) 111.8(4) yes C12 C10 Cl(3) 106.5(9) yes C13 C10 Cl(2) 107.3(3) yes C11 C10 Cl(2) 111.3(2) yes C13 C10 S1 113.4(3) yes C11 C10 S1 106.16(17) yes C12 C10 S1 109.6(15) yes O1 S1 O2 117.09(12) no O1 S1 C1 109.91(11) no O2 S1 C1 110.26(12) no O1 S1 C10 106.66(12) no O2 S1 C10 105.45(12) no C1 S1 C10 106.84(11) no C6 C1 C2 120.6(2) no C6 C1 S1 119.73(17) no C2 C1 S1 119.66(17) no C3 C2 C1 117.4(2) no C3 C2 C8 116.2(2) no C1 C2 C8 126.4(2) no C4 C3 C2 123.4(2) no C5 C4 C3 117.4(2) no C5 C4 C9 121.6(3) no C3 C4 C9 121.0(3) no C4 C5 C6 123.5(2) no C5 C6 C1 117.6(2) no C5 C6 C7 115.8(2) no C1 C6 C7 126.6(2) no Cl(3) C10 S1 109.8(3) no Cl(2) C10 S1 108.68(15) no C10 C12 H12a 109.5 no C10 C12 H12b 109.5 no C10 C12 H12c 109.5 no C10 C13 H13a 109.5 no C10 C13 H13b 109.5 no C10 C13 H13c 109.5 no H12a C12 H12b 109.5 no H12a C12 H12c 109.5 no H12b C12 H12c 109.5 no H13a C13 H13b 109.5 no H13a C13 H13c 109.5 no H13b C13 H13c 109.5 no C4 C3 H3 118.3 no C2 C3 H3 118.3 no C4 C5 H5 118.3 no C6 C5 H5 118.3 no C2 C8 H8a 109.5 no C2 C8 H8b 109.5 no H8a C8 H8b 109.5 no C2 C8 H8c 109.5 no H8a C8 H8c 109.5 no H8b C8 H8c 109.5 no C6 C7 H7a 109.5 no C6 C7 H7b 109.5 no H7a C7 H7b 109.5 no C6 C7 H7c 109.5 no H7a C7 H7c 109.5 no H7b C7 H7c 109.5 no C4 C9 H9a 109.5 no C4 C9 H9b 109.5 no H9a C9 H9b 109.5 no C4 C9 H9c 109.5 no H9a C9 H9c 109.5 no H9b C9 H9c 109.5 no C10 C11 H11a 109.5 no C10 C11 H11b 109.5 no H11a C11 H11b 109.5 no C10 C11 H11c 109.5 no H11a C11 H11c 109.5 no H11b C11 H11c 109.5 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 Cl(2) C10 . 1.763(3) yes Cl(3) C10 . 1.712(5) yes C12 C10 . 1.556(8) yes C13 C10 . 1.517(5) yes C11 C10 . 1.566(3) yes S1 C10 . 1.839(3) yes S1 O1 . 1.4326(19) no S1 O2 . 1.434(2) no S1 C1 . 1.789(2) no C1 C6 . 1.412(3) no C1 C2 . 1.414(3) no C2 C3 . 1.386(3) no C2 C8 . 1.513(3) no C3 C4 . 1.378(4) no C4 C5 . 1.376(4) no C4 C9 . 1.507(4) no C5 C6 . 1.383(4) no C6 C7 . 1.513(4) no C12 H12a . .9600 no C12 H12b . .9600 no C12 H12c . .9600 no C13 H13a . .9600 no C13 H13b . .9600 no C13 H13c . .9600 no C3 H3 . .9300 no C5 H5 . .9300 no C8 H8a . .9600 no C8 H8b . .9600 no C8 H8c . .9600 no C7 H7a . .9600 no C7 H7b . .9600 no C7 H7c . .9600 no C9 H9a . .9600 no C9 H9b . .9600 no C9 H9c . .9600 no C11 H11a . .9600 no C11 H11b . .9600 no C11 H11c . .9600 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O2 C7 2.805(4) . yes O1 C8 2.765(4) . yes C2 C12 3.47(4) . yes C6 C13 3.577(8) . yes C7 C13 3.503(7) . yes C8 C12 3.53(4) . yes O2 C7 3.341(4) 2_665 yes O2 C9 3.371(4) 2_565 yes 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 O1 S1 C1 C6 156.36(19) no O2 S1 C1 C6 25.8(2) no C10 S1 C1 C6 -88.3(2) no O1 S1 C1 C2 -23.2(2) no O2 S1 C1 C2 -153.74(18) no C10 S1 C1 C2 92.2(2) no C6 C1 C2 C3 3.9(3) no S1 C1 C2 C3 -176.52(17) no C6 C1 C2 C8 -173.7(2) no S1 C1 C2 C8 5.9(3) no C1 C2 C3 C4 -1.4(4) no C8 C2 C3 C4 176.4(2) no C2 C3 C4 C5 -1.3(4) no C2 C3 C4 C9 179.4(2) no C3 C4 C5 C6 1.7(4) no C9 C4 C5 C6 -179.0(2) no C4 C5 C6 C1 .7(4) no C4 C5 C6 C7 -177.9(2) no C2 C1 C6 C5 -3.6(3) no S1 C1 C6 C5 176.86(17) no C2 C1 C6 C7 174.9(2) no S1 C1 C6 C7 -4.7(4) no O1 S1 C10 C13 179.4(3) no O2 S1 C10 C13 -55.5(3) no C1 S1 C10 C13 61.9(3) no O1 S1 C10 C11 -59.7(2) no O2 S1 C10 C11 65.4(2) no C1 S1 C10 C11 -177.23(18) no O1 S1 C10 C12 62.7(10) no O2 S1 C10 C12 -172.2(10) no C1 S1 C10 C12 -54.9(10) no O1 S1 C10 Cl(3) 179.3(5) no O2 S1 C10 Cl(3) -55.6(5) no C1 S1 C10 Cl(3) 61.8(5) no O1 S1 C10 Cl(2) 60.12(16) no O2 S1 C10 Cl(2) -174.72(14) no C1 S1 C10 Cl(2) -57.39(16) no