#------------------------------------------------------------------------------ #$Date: 2011-01-03 14:48:23 +0200 (Mon, 03 Jan 2011) $ #$Revision: 5312 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/7101708.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7101708 loop_ _publ_author_name 'Betson, Mark S' 'Bracegirdle, Ann' 'Clayden, Jonathan' 'Helliwell, Madeleine' 'Lund, Andrew' 'Pickworth, Mark' 'Snape, Timothy J' 'Worrall, Christopher P' _publ_section_title ; Achieving conformational control over C-C, C-N and C-O bonds in biaryls, N,N'-diarylureas and diaryl ethers: advantages of a relay axis. ; _journal_issue 7 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 754 _journal_page_last 756 _journal_year 2007 _chemical_formula_sum 'C22 H30 O3 S' _chemical_formula_weight 374.52 _chemical_name_systematic ; ? ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 98.368(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.3358(11) _cell_length_b 12.2620(17) _cell_length_c 20.222(3) _cell_measurement_reflns_used 7926 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.92 _cell_measurement_theta_min 2.63 _cell_volume 2044.9(5) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _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 0.1272 _diffrn_reflns_av_sigmaI/netI 0.0678 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 14180 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 1.95 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_T_max 0.9328 _exptl_absorpt_correction_T_min 0.9170 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _refine_diff_density_max 0.624 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.071 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 242 _refine_ls_number_reflns 3606 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0560 _refine_ls_R_factor_gt 0.0496 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1009P)^2^+0.0562P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1430 _refine_ls_wR_factor_ref 0.1477 _reflns_number_gt 3062 _reflns_number_total 3606 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file b614618j.txt _[local]_cod_data_source_block s2305m _[local]_cod_cif_authors_sg_H-M P2(1)/c _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 ; _cod_database_code 7101708 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_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags S1 S 0.16658(5) 1.00032(3) 0.32032(2) 0.02077(19) Uani 1 1 d . O1 O 0.20899(14) 0.80034(10) 0.40289(6) 0.0205(3) Uani 1 1 d . O2 O 0.51011(17) 0.53377(11) 0.36976(7) 0.0286(3) Uani 1 1 d . O3 O 0.23552(16) 1.10503(10) 0.29739(7) 0.0276(3) Uani 1 1 d . C1 C 0.3174(2) 0.89656(15) 0.31586(9) 0.0201(4) Uani 1 1 d . C2 C 0.3237(2) 0.80651(15) 0.35886(9) 0.0194(4) Uani 1 1 d . C3 C 0.4327(2) 0.72102(14) 0.35382(9) 0.0206(4) Uani 1 1 d . C4 C 0.5362(2) 0.72864(15) 0.30551(9) 0.0234(4) Uani 1 1 d . H4 H 0.6097 0.6710 0.3007 0.028 Uiso 1 1 calc R C5 C 0.5328(2) 0.82016(16) 0.26413(9) 0.0245(4) Uani 1 1 d . H5 H 0.6049 0.8242 0.2319 0.029 Uiso 1 1 calc R C6 C 0.4259(2) 0.90494(16) 0.26941(9) 0.0238(4) Uani 1 1 d . H6 H 0.4261 0.9678 0.2420 0.029 Uiso 1 1 calc R C7 C 0.2604(2) 0.82052(14) 0.47139(9) 0.0200(4) Uani 1 1 d . C8 C 0.1448(2) 0.80350(14) 0.51518(9) 0.0213(4) Uani 1 1 d . C9 C 0.2012(2) 0.82278(16) 0.58325(9) 0.0261(4) Uani 1 1 d . H9 H 0.1283 0.8122 0.6147 0.031 Uiso 1 1 calc R C10 C 0.3589(2) 0.85663(16) 0.60666(10) 0.0284(5) Uani 1 1 d . H10 H 0.3921 0.8677 0.6531 0.034 Uiso 1 1 calc R C11 C 0.4671(2) 0.87398(16) 0.56178(10) 0.0283(5) Uani 1 1 d . H11 H 0.5746 0.8977 0.5772 0.034 Uiso 1 1 calc R C12 C 0.4165(2) 0.85630(15) 0.49371(9) 0.0241(4) Uani 1 1 d . H12 H 0.4895 0.8689 0.4626 0.029 Uiso 1 1 calc R C13 C -0.0329(2) 0.77118(16) 0.49058(10) 0.0241(4) Uani 1 1 d . C14 C -0.1294(2) 0.75300(18) 0.54953(10) 0.0332(5) Uani 1 1 d . H14A H -0.2403 0.7306 0.5322 0.050 Uiso 1 1 calc R H14B H -0.1321 0.8210 0.5748 0.050 Uiso 1 1 calc R H14C H -0.0767 0.6959 0.5790 0.050 Uiso 1 1 calc R C15 C -0.1181(2) 0.86415(17) 0.44715(10) 0.0288(5) Uani 1 1 d . H15A H -0.0549 0.8821 0.4114 0.043 Uiso 1 1 calc R H15B H -0.1264 0.9287 0.4750 0.043 Uiso 1 1 calc R H15C H -0.2270 0.8405 0.4275 0.043 Uiso 1 1 calc R C16 C -0.0408(3) 0.66378(18) 0.45027(11) 0.0335(5) Uani 1 1 d . H16A H 0.0102 0.6745 0.4100 0.050 Uiso 1 1 calc R H16B H -0.1543 0.6424 0.4374 0.050 Uiso 1 1 calc R H16C H 0.0168 0.6063 0.4778 0.050 Uiso 1 1 calc R C17 C 0.4387(2) 0.62338(14) 0.39983(9) 0.0234(4) Uani 1 1 d . H17A H 0.5037 0.6410 0.4435 0.028 Uiso 1 1 calc R H17B H 0.3277 0.6040 0.4076 0.028 Uiso 1 1 calc R C18 C 0.5331(3) 0.44192(16) 0.41333(11) 0.0363(5) Uani 1 1 d . H18A H 0.6085 0.4612 0.4534 0.054 Uiso 1 1 calc R H18B H 0.5779 0.3812 0.3903 0.054 Uiso 1 1 calc R H18C H 0.4288 0.4202 0.4262 0.054 Uiso 1 1 calc R C19 C 0.0103(2) 0.95331(15) 0.24921(9) 0.0236(4) Uani 1 1 d . C20 C -0.0257(2) 0.83230(16) 0.25625(10) 0.0276(5) Uani 1 1 d . H20A H -0.1136 0.8106 0.2211 0.041 Uiso 1 1 calc R H20B H -0.0584 0.8188 0.3002 0.041 Uiso 1 1 calc R H20C H 0.0718 0.7897 0.2520 0.041 Uiso 1 1 calc R C21 C -0.1388(2) 1.02325(17) 0.25656(12) 0.0345(5) Uani 1 1 d . H21A H -0.1107 1.1006 0.2542 0.052 Uiso 1 1 calc R H21B H -0.1743 1.0080 0.2997 0.052 Uiso 1 1 calc R H21C H -0.2267 1.0058 0.2204 0.052 Uiso 1 1 calc R C22 C 0.0724(3) 0.9780(2) 0.18340(11) 0.0383(5) Uani 1 1 d . H22A H 0.1534 0.9234 0.1756 0.058 Uiso 1 1 calc R H22B H 0.1218 1.0507 0.1857 0.058 Uiso 1 1 calc R H22C H -0.0183 0.9758 0.1467 0.058 Uiso 1 1 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0224(3) 0.0225(3) 0.0180(3) -0.00047(17) 0.0050(2) 0.00117(16) O1 0.0201(7) 0.0307(7) 0.0123(7) -0.0005(5) 0.0074(5) 0.0000(5) O2 0.0433(8) 0.0267(7) 0.0182(7) 0.0025(6) 0.0129(6) 0.0090(6) O3 0.0304(8) 0.0228(7) 0.0295(8) 0.0014(6) 0.0043(6) -0.0022(5) C1 0.0215(9) 0.0235(9) 0.0159(9) -0.0014(7) 0.0046(7) -0.0005(7) C2 0.0180(9) 0.0278(10) 0.0137(9) -0.0004(7) 0.0070(7) -0.0026(7) C3 0.0227(9) 0.0249(9) 0.0148(9) -0.0009(7) 0.0050(7) -0.0015(7) C4 0.0229(10) 0.0293(10) 0.0191(10) -0.0017(8) 0.0069(7) 0.0022(8) C5 0.0235(10) 0.0330(10) 0.0193(10) -0.0002(8) 0.0107(8) -0.0015(8) C6 0.0248(10) 0.0292(10) 0.0183(10) 0.0036(8) 0.0057(7) -0.0025(8) C7 0.0251(10) 0.0215(9) 0.0136(9) -0.0001(7) 0.0036(7) 0.0034(7) C8 0.0280(10) 0.0205(9) 0.0169(9) 0.0007(7) 0.0083(8) 0.0037(7) C9 0.0349(11) 0.0300(10) 0.0153(10) -0.0001(8) 0.0097(8) 0.0052(8) C10 0.0358(11) 0.0336(11) 0.0155(10) -0.0038(8) 0.0025(8) 0.0085(8) C11 0.0261(10) 0.0323(11) 0.0260(11) -0.0073(8) 0.0015(8) 0.0028(8) C12 0.0261(10) 0.0282(10) 0.0197(10) -0.0024(8) 0.0085(8) 0.0018(8) C13 0.0263(10) 0.0272(10) 0.0213(10) -0.0018(8) 0.0122(8) -0.0015(8) C14 0.0326(11) 0.0428(12) 0.0276(12) 0.0031(9) 0.0159(9) -0.0011(9) C15 0.0241(10) 0.0401(12) 0.0234(11) 0.0017(9) 0.0077(8) 0.0012(8) C16 0.0323(11) 0.0336(11) 0.0383(12) -0.0087(9) 0.0172(10) -0.0079(9) C17 0.0273(10) 0.0266(10) 0.0183(10) 0.0000(8) 0.0098(8) 0.0035(8) C18 0.0538(14) 0.0282(11) 0.0297(12) 0.0075(9) 0.0158(10) 0.0111(10) C19 0.0243(10) 0.0263(10) 0.0200(10) 0.0017(7) 0.0024(8) -0.0010(8) C20 0.0286(10) 0.0267(10) 0.0270(11) -0.0023(8) 0.0025(8) -0.0005(8) C21 0.0292(11) 0.0279(10) 0.0441(14) -0.0027(9) -0.0023(10) 0.0019(9) C22 0.0370(12) 0.0571(14) 0.0199(11) 0.0062(10) 0.0009(9) -0.0126(11) 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 O3 S1 C1 106.63(8) O3 S1 C19 106.14(8) C1 S1 C19 98.97(8) C2 O1 C7 118.47(13) C18 O2 C17 111.82(14) C6 C1 C2 120.33(16) C6 C1 S1 120.39(14) C2 C1 S1 119.27(13) C3 C2 O1 121.07(15) C3 C2 C1 120.70(16) O1 C2 C1 118.01(15) C4 C3 C2 118.29(16) C4 C3 C17 120.94(16) C2 C3 C17 120.77(15) C5 C4 C3 120.75(17) C5 C4 H4 119.6 C3 C4 H4 119.6 C6 C5 C4 120.95(17) C6 C5 H5 119.5 C4 C5 H5 119.5 C5 C6 C1 118.88(17) C5 C6 H6 120.6 C1 C6 H6 120.6 C12 C7 O1 120.82(16) C12 C7 C8 122.38(17) O1 C7 C8 116.80(16) C9 C8 C7 115.20(17) C9 C8 C13 121.75(17) C7 C8 C13 123.00(16) C10 C9 C8 123.10(18) C10 C9 H9 118.5 C8 C9 H9 118.5 C11 C10 C9 119.65(18) C11 C10 H10 120.2 C9 C10 H10 120.2 C10 C11 C12 119.33(18) C10 C11 H11 120.3 C12 C11 H11 120.3 C7 C12 C11 120.32(17) C7 C12 H12 119.8 C11 C12 H12 119.8 C8 C13 C16 110.71(15) C8 C13 C15 109.47(16) C16 C13 C15 110.35(17) C8 C13 C14 111.73(16) C16 C13 C14 107.26(16) C15 C13 C14 107.24(15) C13 C14 H14A 109.5 C13 C14 H14B 109.5 H14A C14 H14B 109.5 C13 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C13 C15 H15A 109.5 C13 C15 H15B 109.5 H15A C15 H15B 109.5 C13 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C13 C16 H16A 109.5 C13 C16 H16B 109.5 H16A C16 H16B 109.5 C13 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 O2 C17 C3 109.02(14) O2 C17 H17A 109.9 C3 C17 H17A 109.9 O2 C17 H17B 109.9 C3 C17 H17B 109.9 H17A C17 H17B 108.3 O2 C18 H18A 109.5 O2 C18 H18B 109.5 H18A C18 H18B 109.5 O2 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C20 C19 C22 111.77(17) C20 C19 C21 111.19(16) C22 C19 C21 110.82(17) C20 C19 S1 110.48(13) C22 C19 S1 108.66(13) C21 C19 S1 103.58(13) C19 C20 H20A 109.5 C19 C20 H20B 109.5 H20A C20 H20B 109.5 C19 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C19 C21 H21A 109.5 C19 C21 H21B 109.5 H21A C21 H21B 109.5 C19 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C19 C22 H22A 109.5 C19 C22 H22B 109.5 H22A C22 H22B 109.5 C19 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 O3 1.5070(13) S1 C1 1.8004(18) S1 C19 1.8847(19) O1 C2 1.400(2) O1 C7 1.411(2) O2 C18 1.426(2) O2 C17 1.427(2) C1 C6 1.399(2) C1 C2 1.402(3) C2 C3 1.400(3) C3 C4 1.398(2) C3 C17 1.513(2) C4 C5 1.398(3) C4 H4 0.9500 C5 C6 1.384(3) C5 H5 0.9500 C6 H6 0.9500 C7 C12 1.385(3) C7 C8 1.416(2) C8 C9 1.408(3) C8 C13 1.544(3) C9 C10 1.394(3) C9 H9 0.9500 C10 C11 1.385(3) C10 H10 0.9500 C11 C12 1.397(3) C11 H11 0.9500 C12 H12 0.9500 C13 C16 1.545(3) C13 C15 1.547(3) C13 C14 1.548(2) C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 C15 H15A 0.9800 C15 H15B 0.9800 C15 H15C 0.9800 C16 H16A 0.9800 C16 H16B 0.9800 C16 H16C 0.9800 C17 H17A 0.9900 C17 H17B 0.9900 C18 H18A 0.9800 C18 H18B 0.9800 C18 H18C 0.9800 C19 C20 1.525(3) C19 C22 1.527(3) C19 C21 1.535(3) C20 H20A 0.9800 C20 H20B 0.9800 C20 H20C 0.9800 C21 H21A 0.9800 C21 H21B 0.9800 C21 H21C 0.9800 C22 H22A 0.9800 C22 H22B 0.9800 C22 H22C 0.9800 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 O3 S1 C1 C6 -28.46(17) C19 S1 C1 C6 81.47(16) O3 S1 C1 C2 152.37(15) C19 S1 C1 C2 -97.70(16) C7 O1 C2 C3 78.5(2) C7 O1 C2 C1 -106.90(18) C6 C1 C2 C3 -3.3(3) S1 C1 C2 C3 175.91(14) C6 C1 C2 O1 -177.93(15) S1 C1 C2 O1 1.2(2) O1 C2 C3 C4 175.39(15) C1 C2 C3 C4 0.9(3) O1 C2 C3 C17 -5.0(3) C1 C2 C3 C17 -179.52(17) C2 C3 C4 C5 1.1(3) C17 C3 C4 C5 -178.52(17) C3 C4 C5 C6 -0.7(3) C4 C5 C6 C1 -1.7(3) C2 C1 C6 C5 3.6(3) S1 C1 C6 C5 -175.55(15) C2 O1 C7 C12 6.4(2) C2 O1 C7 C8 -174.21(15) C12 C7 C8 C9 -1.6(3) O1 C7 C8 C9 179.04(15) C12 C7 C8 C13 175.73(17) O1 C7 C8 C13 -3.6(2) C7 C8 C9 C10 0.2(3) C13 C8 C9 C10 -177.13(17) C8 C9 C10 C11 0.8(3) C9 C10 C11 C12 -0.6(3) O1 C7 C12 C11 -178.75(16) C8 C7 C12 C11 1.9(3) C10 C11 C12 C7 -0.8(3) C9 C8 C13 C16 -124.90(19) C7 C8 C13 C16 57.9(2) C9 C8 C13 C15 113.22(19) C7 C8 C13 C15 -63.9(2) C9 C8 C13 C14 -5.4(2) C7 C8 C13 C14 177.41(17) C18 O2 C17 C3 174.60(16) C4 C3 C17 O2 -21.9(2) C2 C3 C17 O2 158.51(16) O3 S1 C19 C20 160.77(13) C1 S1 C19 C20 50.45(14) O3 S1 C19 C22 37.81(16) C1 S1 C19 C22 -72.52(15) O3 S1 C19 C21 -80.07(14) C1 S1 C19 C21 169.61(13)