#------------------------------------------------------------------------------ #$Date: 2018-03-23 03:59:16 +0200 (Fri, 23 Mar 2018) $ #$Revision: 207066 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/90/1549094.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_1549094 loop_ _publ_author_name 'van der Lee, Arie' 'Roche, Gille H.' 'Wantz, Guillaume' 'Moreau, Jo\"el J.E.' 'DAUTEL, olivier joseph' 'Filhol, Jean-S\'ebastien' _publ_section_title ; Experimental and theoretical evidence of a supercritical-like transition in an organic semiconductor presenting colossal uniaxial negative thermal expansion ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C8SC00159F _journal_year 2018 _chemical_formula_moiety 'C26 H32 O2 S2' _chemical_formula_sum 'C26 H32 O2 S2' _chemical_formula_weight 440.66 _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-I 2ya' _symmetry_space_group_name_H-M 'I 1 2/a 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary iterative _audit_update_record ; 2017-12-12 deposited with the CCDC. 2018-03-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.879(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.7604(8) _cell_length_b 5.9132(6) _cell_length_c 49.450(4) _cell_measurement_reflns_used 1440 _cell_measurement_temperature 95 _cell_measurement_theta_max 28.3770 _cell_measurement_theta_min 3.3240 _cell_volume 2257.3(4) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _diffrn_ambient_temperature 95 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0143 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.897 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -2.00 85.00 1.00 8.00 -- 16.62 57.00 0.00 87 2 \w -12.00 86.00 1.00 8.00 -- 16.62 77.00 90.00 98 3 \w -24.00 24.00 1.00 8.00 -- -17.25-100.00-120.00 48 4 \w 34.00 91.00 1.00 8.00 -- 16.62 179.00-150.00 57 5 \w 32.00 91.00 1.00 8.00 -- 16.62-179.00 -30.00 59 6 \w -52.00 35.00 1.00 8.00 -- 16.62 -57.00 -30.00 87 ; _diffrn_measurement_device Area _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0662125518 _diffrn_orient_matrix_UB_12 -0.0493813921 _diffrn_orient_matrix_UB_13 0.0069266320 _diffrn_orient_matrix_UB_21 0.0598796944 _diffrn_orient_matrix_UB_22 -0.0155517118 _diffrn_orient_matrix_UB_23 0.0117080756 _diffrn_orient_matrix_UB_31 -0.0218152044 _diffrn_orient_matrix_UB_32 0.1081085473 _diffrn_orient_matrix_UB_33 0.0048112850 _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.049 _diffrn_reflns_av_unetI/netI 0.0518 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 62 _diffrn_reflns_limit_l_min -67 _diffrn_reflns_number 9808 _diffrn_reflns_theta_full 25.005 _diffrn_reflns_theta_max 29.075 _diffrn_reflns_theta_min 1.656 _exptl_absorpt_coefficient_mu 0.257 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.53668 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.41 _refine_diff_density_min -0.77 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 1.1160 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 2599 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0641 _refine_ls_R_factor_gt 0.0520 _refine_ls_shift/su_max 0.0006651 _refine_ls_shift/su_mean 0.0000642 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 878. 0.110E+04 492. ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0707 _refine_ls_wR_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.0652 _reflns_limit_h_max 10 _reflns_limit_h_min -10 _reflns_limit_k_max 7 _reflns_limit_k_min 0 _reflns_limit_l_max 66 _reflns_limit_l_min 0 _reflns_number_gt 2257 _reflns_number_total 2715 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _oxford_refine_ls_r_factor_ref 0.0604 _oxford_refine_ls_scale 3.89(3) _oxford_reflns_number_all 2715 _oxford_reflns_threshold_expression_ref I>0.0\s(I) _iucr_refine_instructions_details ; # # Punched on 10/02/16 at 11:15: 2 # #LIST 12 BLOCK SCALE X'S U'S RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 6,X'S) H ( 61,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 92,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) H ( 102,X'S) RIDE C ( 11,X'S) H ( 112,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S) RIDE C ( 13,X'S) H ( 132,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 142,X'S) H ( 141,X'S) RIDE O ( 15,X'S) H ( 151,X'S) H ( 152,X'S) END # # Punched on 10/02/16 at 11:15: 2 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _cod_data_source_file c8sc00159f2.cif _cod_data_source_block 95K _cod_original_cell_volume 2257.3(2) _cod_original_sg_symbol_H-M 'I 1 2/a 1 ' _cod_database_code 1549094 _cell_oxdiff_length_a 7.7600(9) _cell_oxdiff_length_b 5.9175(8) _cell_oxdiff_length_c 49.423(5) _cell_oxdiff_angle_alpha 89.878(9) _cell_oxdiff_angle_beta 95.951(9) _cell_oxdiff_angle_gamma 89.909(10) _cell_oxdiff_volume 2257.3(5) _oxdiff_exptl_absorpt_empirical_full_min 0.600 _oxdiff_exptl_absorpt_empirical_full_max 1.676 _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _montpellier_reflns_maxres 0.73 _montpellier_reflns_completeness_maxres 90.15 _montpellier_reflns_redundancy_maxres 3.47 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x+1/2,y+1/2,z+1/2 -x+1/2,-y+1/2,-z+1/2 -x+1/2,y,-z x+1/2,-y,z -x+1,y+1/2,-z+1/2 x+1,-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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn S1 S 0.83825(7) 0.54109(10) 0.731698(11) 0.0236 1.0000 Uani . C2 C 0.7398(3) 0.3710(4) 0.70568(4) 0.0217 1.0000 Uani . C3 C 0.6758(3) 0.1664(4) 0.71529(4) 0.0203 1.0000 Uani . C4 C 0.7086(3) 0.1578(4) 0.74433(4) 0.0210 1.0000 Uani . C5 C 0.5908(3) 0.0173(4) 0.69656(4) 0.0249 1.0000 Uani . C6 C 0.5708(3) 0.0739(4) 0.66930(4) 0.0270 1.0000 Uani . C7 C 0.6338(3) 0.2780(4) 0.65979(4) 0.0265 1.0000 Uani . C8 C 0.7202(3) 0.4267(4) 0.67810(4) 0.0249 1.0000 Uani . C9 C 0.6134(3) 0.3336(5) 0.62981(4) 0.0312 1.0000 Uani . C10 C 0.7501(3) 0.2195(5) 0.61441(4) 0.0298 1.0000 Uani . C11 C 0.7488(3) 0.3017(5) 0.58510(4) 0.0322 1.0000 Uani . C12 C 0.8940(3) 0.1973(5) 0.57091(4) 0.0329 1.0000 Uani . C13 C 0.9081(3) 0.2946(5) 0.54261(4) 0.0348 1.0000 Uani . C14 C 1.0635(3) 0.1993(5) 0.53038(5) 0.0380 1.0000 Uani . O15 O 1.0805(2) 0.2975(4) 0.50429(3) 0.0402 1.0000 Uani . H51 H 0.5493 -0.1216 0.7023 0.0291 1.0000 Uiso R H61 H 0.5118 -0.0261 0.6565 0.0319 1.0000 Uiso R H81 H 0.7632 0.5666 0.6722 0.0306 1.0000 Uiso R H91 H 0.6240 0.4953 0.6276 0.0366 1.0000 Uiso R H92 H 0.4993 0.2799 0.6222 0.0361 1.0000 Uiso R H101 H 0.8632 0.2570 0.6238 0.0351 1.0000 Uiso R H102 H 0.7340 0.0570 0.6147 0.0350 1.0000 Uiso R H111 H 0.7614 0.4678 0.5851 0.0385 1.0000 Uiso R H112 H 0.6382 0.2645 0.5753 0.0386 1.0000 Uiso R H121 H 1.0051 0.2261 0.5816 0.0398 1.0000 Uiso R H122 H 0.8750 0.0354 0.5695 0.0389 1.0000 Uiso R H131 H 0.9216 0.4587 0.5444 0.0415 1.0000 Uiso R H132 H 0.8032 0.2582 0.5313 0.0420 1.0000 Uiso R H141 H 1.1708 0.2259 0.5425 0.0450 1.0000 Uiso R H142 H 1.0499 0.0386 0.5277 0.0456 1.0000 Uiso R H151 H 1.0398 0.4231 0.5046 0.0640 0.5000 Uiso R H152 H 1.1853 0.3038 0.5033 0.0640 0.5000 Uiso 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 0.0296(3) 0.0254(3) 0.0171(2) 0.0000(2) 0.00872(19) -0.0037(3) C2 0.0204(10) 0.0257(12) 0.0202(10) -0.0020(9) 0.0079(8) -0.0006(9) C3 0.0180(10) 0.0242(12) 0.0201(10) 0.0013(9) 0.0093(8) 0.0032(9) C4 0.0189(10) 0.0233(11) 0.0223(10) 0.0008(9) 0.0093(8) 0.0007(9) C5 0.0274(11) 0.0289(13) 0.0198(10) -0.0017(9) 0.0089(8) -0.0029(10) C6 0.0265(11) 0.0350(14) 0.0200(10) -0.0058(10) 0.0043(8) 0.0000(11) C7 0.0256(11) 0.0367(14) 0.0179(10) 0.0009(10) 0.0058(8) 0.0068(10) C8 0.0248(11) 0.0301(13) 0.0215(10) 0.0032(10) 0.0102(8) 0.0046(10) C9 0.0339(13) 0.0430(15) 0.0174(10) 0.0012(11) 0.0060(9) 0.0050(12) C10 0.0363(13) 0.0388(15) 0.0158(10) 0.0019(10) 0.0098(9) 0.0024(12) C11 0.0356(13) 0.0453(16) 0.0165(10) 0.0037(11) 0.0064(9) 0.0030(12) C12 0.0377(14) 0.0432(15) 0.0190(11) 0.0019(11) 0.0095(9) 0.0004(12) C13 0.0379(14) 0.0484(17) 0.0200(11) 0.0016(12) 0.0120(10) -0.0013(13) C14 0.0476(16) 0.0469(17) 0.0222(11) 0.0040(12) 0.0162(11) 0.0032(14) O15 0.0488(11) 0.0517(12) 0.0232(8) 0.0044(9) 0.0183(8) -0.0008(10) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' loop_ _montpellier_diffrn_reflns_class_number _montpellier_diffrn_reflns_class_d_res_high _montpellier_diffrn_reflns_class_d_res_low _montpellier_diffrn_reflns_class_redundancy _montpellier_diffrn_reflns_class_av_i/ui _diffrn_reflns_class_av_R_eq _montpellier_diffrn_reflns_class_completeness_shell _montpellier_diffrn_reflns_class_cumul_completeness 0 100.0 1.71 5.6 68.13 0.035 99.7 99.66 1 1.70 1.33 4.8 27.26 0.040 100.0 99.83 2 1.33 1.15 4.3 22.01 0.055 100.0 99.89 3 1.15 1.04 3.8 13.40 0.068 100.0 99.92 4 1.04 0.96 3.4 10.84 0.069 100.0 99.93 5 0.96 0.91 3.2 8.65 0.097 100.0 99.94 6 0.91 0.86 3.1 6.69 0.102 100.0 99.95 7 0.86 0.82 2.8 5.99 0.124 99.7 99.92 8 0.82 0.79 2.4 5.17 0.149 96.4 99.52 9 0.79 0.73 1.4 3.60 0.151 49.3 90.15 loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C4 4_656 S1 C2 . 90.36(10) yes S1 . C2 C3 . 112.89(15) yes S1 . C2 C8 . 125.40(18) yes C3 . C2 C8 . 121.7(2) yes C2 . C3 C4 . 109.62(19) yes C2 . C3 C5 . 118.55(19) yes C4 . C3 C5 . 131.8(2) yes C3 . C4 S1 4_656 132.88(18) yes C3 . C4 C4 4_656 114.4(2) yes S1 4_656 C4 C4 4_656 112.7(2) yes C3 . C5 C6 . 119.5(2) yes C3 . C5 H51 . 120.5 no C6 . C5 H51 . 120.0 no C5 . C6 C7 . 121.8(2) yes C5 . C6 H61 . 119.9 no C7 . C6 H61 . 118.3 no C6 . C7 C8 . 119.3(2) yes C6 . C7 C9 . 120.8(2) yes C8 . C7 C9 . 119.9(2) yes C2 . C8 C7 . 119.1(2) yes C2 . C8 H81 . 120.0 no C7 . C8 H81 . 120.9 no C7 . C9 C10 . 112.7(2) yes C7 . C9 H91 . 108.9 no C10 . C9 H91 . 108.1 no C7 . C9 H92 . 107.7 no C10 . C9 H92 . 108.3 no H91 . C9 H92 . 111.2 no C9 . C10 C11 . 113.3(2) yes C9 . C10 H101 . 107.4 no C11 . C10 H101 . 107.4 no C9 . C10 H102 . 109.5 no C11 . C10 H102 . 110.0 no H101 . C10 H102 . 109.2 no C10 . C11 C12 . 112.1(2) yes C10 . C11 H111 . 108.8 no C12 . C11 H111 . 109.1 no C10 . C11 H112 . 108.8 no C12 . C11 H112 . 109.8 no H111 . C11 H112 . 108.1 no C11 . C12 C13 . 113.3(2) yes C11 . C12 H121 . 109.6 no C13 . C12 H121 . 106.6 no C11 . C12 H122 . 108.7 no C13 . C12 H122 . 109.2 no H121 . C12 H122 . 109.3 no C12 . C13 C14 . 111.1(2) yes C12 . C13 H131 . 107.8 no C14 . C13 H131 . 108.9 no C12 . C13 H132 . 108.3 no C14 . C13 H132 . 110.1 no H131 . C13 H132 . 110.5 no C13 . C14 O15 . 111.1(2) yes C13 . C14 H141 . 110.9 no O15 . C14 H141 . 109.3 no C13 . C14 H142 . 110.0 no O15 . C14 H142 . 107.2 no H141 . C14 H142 . 108.3 no C14 . O15 H151 . 106.3 no C14 . O15 H152 . 104.7 no H151 . O15 H152 . 110.5 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 S1 C4 4_656 1.735(2) yes S1 C2 . 1.746(2) yes C2 C3 . 1.408(3) yes C2 C8 . 1.396(3) yes C3 C4 . 1.433(3) yes C3 C5 . 1.395(3) yes C4 C4 4_656 1.357(4) yes C5 C6 . 1.382(3) yes C5 H51 . 0.937 no C6 C7 . 1.401(3) yes C6 H61 . 0.949 no C7 C8 . 1.385(3) yes C7 C9 . 1.511(3) yes C8 H81 . 0.949 no C9 C10 . 1.525(3) yes C9 H91 . 0.967 no C9 H92 . 0.978 no C10 C11 . 1.528(3) yes C10 H101 . 0.976 no C10 H102 . 0.970 no C11 C12 . 1.519(3) yes C11 H111 . 0.987 no C11 H112 . 0.967 no C12 C13 . 1.528(3) yes C12 H121 . 0.977 no C12 H122 . 0.970 no C13 C14 . 1.512(3) yes C13 H131 . 0.979 no C13 H132 . 0.965 no C14 O15 . 1.433(3) yes C14 H141 . 0.987 no C14 H142 . 0.963 no O15 H151 . 0.808 no O15 H152 . 0.820 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_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag O15 H151 O15 2_766 164.74(10) 0.808 1.926 2.714(3) yes O15 H152 O15 5_756 171.00(9) 0.820 1.894 2.708(3) yes