# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-(2-methoxybenzyl)-1,3,4-thiadiazole-2(3H)-thione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N2 O2 S' _chemical_formula_sum 'C10 H10 N2 O2 S' _chemical_formula_weight 222.26 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_space_group_name_Hall '-P 2yn ' 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' _cell_length_a 11.6420(9) _cell_length_b 4.6349(4) _cell_length_c 18.8292(18) _cell_angle_alpha 90.00 _cell_angle_beta 95.453(5) _cell_angle_gamma 90.00 _cell_volume 1011.42(15) _cell_formula_units_Z 4 _cell_measurement_temperature 91(2) _cell_measurement_reflns_used 2473 _cell_measurement_theta_min 3.52 _cell_measurement_theta_max 25.62 _exptl_crystal_description 'rectangular plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.460 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7004 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details 'SADABS (Bruker, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 91(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11652 _diffrn_reflns_av_R_equivalents 0.0421 _diffrn_reflns_av_sigmaI/netI 0.0351 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.85 _diffrn_reflns_theta_max 26.29 _reflns_number_total 2046 _reflns_number_gt 1662 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'APEX2 and SAINT (Bruker, 2011)' _computing_data_reduction 'SAINT (Bruker, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement ; SHELXL-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999) ; _computing_molecular_graphics ; Mercury (Macrae et al., 2008) ; _computing_publication_material ; SHELXL-97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009), PublCIF (Westrip 2010) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0286P)^2^+0.5724P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2046 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0736 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.74914(9) 0.1114(2) 0.56246(6) 0.0170(3) Uani 1 1 d . . . C2 C 0.65991(14) 0.2533(4) 0.52457(10) 0.0165(4) Uani 1 1 d . . . S2 S 0.60877(4) 0.16163(10) 0.44268(3) 0.02091(14) Uani 1 1 d . . . N3 N 0.63160(13) 0.4633(3) 0.56768(8) 0.0192(3) Uani 1 1 d . . . H3N H 0.5719(17) 0.581(4) 0.5615(11) 0.023 Uiso 1 1 d . . . N4 N 0.69947(12) 0.4647(3) 0.63239(8) 0.0197(3) Uani 1 1 d . . . C5 C 0.76852(14) 0.2516(4) 0.62685(10) 0.0146(4) Uani 1 1 d . . . C6 C 0.86036(14) 0.1416(4) 0.68062(10) 0.0163(4) Uani 1 1 d . . . H6A H 0.8954 -0.0333 0.6616 0.020 Uiso 1 1 calc R . . H6B H 0.8251 0.0861 0.7245 0.020 Uiso 1 1 calc R . . C11 C 0.95381(13) 0.3633(3) 0.69931(10) 0.0149(4) Uani 1 1 d . . . C12 C 1.03270(14) 0.4284(4) 0.64987(10) 0.0171(4) Uani 1 1 d . . . O12 O 1.01750(10) 0.2773(3) 0.58705(7) 0.0203(3) Uani 1 1 d . . . C121 C 1.10787(16) 0.2963(5) 0.54055(11) 0.0292(5) Uani 1 1 d . . . H12A H 1.1145 0.4959 0.5243 0.044 Uiso 1 1 calc R . . H12B H 1.0899 0.1699 0.4993 0.044 Uiso 1 1 calc R . . H12C H 1.1810 0.2361 0.5663 0.044 Uiso 1 1 calc R . . C13 C 1.11845(14) 0.6332(4) 0.66600(11) 0.0228(4) Uani 1 1 d . . . H13 H 1.1720 0.6771 0.6325 0.027 Uiso 1 1 calc R . . C14 C 1.12523(16) 0.7726(4) 0.73131(12) 0.0258(5) Uani 1 1 d . . . H14 H 1.1827 0.9156 0.7420 0.031 Uiso 1 1 calc R . . C15 C 1.04953(16) 0.7067(4) 0.78122(11) 0.0242(4) Uani 1 1 d . . . H15 H 1.0558 0.8007 0.8263 0.029 Uiso 1 1 calc R . . C16 C 0.96399(15) 0.5012(4) 0.76482(10) 0.0190(4) Uani 1 1 d . . . H16 H 0.9119 0.4550 0.7990 0.023 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 O1 0.0163(6) 0.0186(6) 0.0157(7) -0.0006(5) -0.0001(5) 0.0031(5) C2 0.0127(8) 0.0182(9) 0.0188(10) 0.0021(7) 0.0021(7) 0.0007(7) S2 0.0175(2) 0.0277(3) 0.0169(3) -0.0044(2) -0.00177(17) 0.00442(18) N3 0.0166(7) 0.0204(8) 0.0195(9) -0.0034(7) -0.0044(6) 0.0062(6) N4 0.0176(7) 0.0232(8) 0.0172(9) -0.0024(7) -0.0036(6) 0.0040(6) C5 0.0155(8) 0.0148(9) 0.0140(10) 0.0007(7) 0.0040(7) -0.0033(6) C6 0.0176(8) 0.0161(9) 0.0152(10) 0.0030(7) 0.0015(7) 0.0003(7) C11 0.0134(8) 0.0129(8) 0.0175(10) 0.0034(7) -0.0031(7) 0.0032(6) C12 0.0163(8) 0.0171(9) 0.0173(10) 0.0027(7) -0.0022(7) 0.0042(7) O12 0.0202(6) 0.0242(7) 0.0174(8) 0.0004(5) 0.0059(5) 0.0008(5) C121 0.0243(10) 0.0408(12) 0.0240(12) 0.0059(9) 0.0108(8) 0.0071(9) C13 0.0150(8) 0.0216(10) 0.0312(12) 0.0088(8) -0.0005(8) 0.0018(7) C14 0.0206(9) 0.0167(9) 0.0372(13) 0.0032(9) -0.0121(8) -0.0010(7) C15 0.0296(10) 0.0170(9) 0.0233(12) -0.0021(8) -0.0106(8) 0.0049(8) C16 0.0215(9) 0.0179(9) 0.0168(10) 0.0017(7) -0.0018(7) 0.0055(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.371(2) . ? O1 C5 1.375(2) . ? C2 N3 1.329(2) . ? C2 S2 1.6548(19) . ? N3 N4 1.388(2) . ? N3 H3N 0.88(2) . ? N4 C5 1.284(2) . ? C5 C6 1.491(2) . ? C6 C11 1.513(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C11 C16 1.384(2) . ? C11 C12 1.401(2) . ? C12 O12 1.372(2) . ? C12 C13 1.390(2) . ? O12 C121 1.434(2) . ? C121 H12A 0.9800 . ? C121 H12B 0.9800 . ? C121 H12C 0.9800 . ? C13 C14 1.385(3) . ? C13 H13 0.9500 . ? C14 C15 1.382(3) . ? C14 H14 0.9500 . ? C15 C16 1.391(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C5 106.54(13) . . ? N3 C2 O1 104.68(15) . . ? N3 C2 S2 132.00(14) . . ? O1 C2 S2 123.32(13) . . ? C2 N3 N4 112.71(14) . . ? C2 N3 H3N 127.6(13) . . ? N4 N3 H3N 119.2(13) . . ? C5 N4 N3 103.51(14) . . ? N4 C5 O1 112.57(15) . . ? N4 C5 C6 128.46(16) . . ? O1 C5 C6 118.95(14) . . ? C5 C6 C11 112.27(14) . . ? C5 C6 H6A 109.2 . . ? C11 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? C11 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C16 C11 C12 119.10(16) . . ? C16 C11 C6 121.31(15) . . ? C12 C11 C6 119.59(16) . . ? O12 C12 C13 124.62(16) . . ? O12 C12 C11 115.09(15) . . ? C13 C12 C11 120.29(17) . . ? C12 O12 C121 116.95(14) . . ? O12 C121 H12A 109.5 . . ? O12 C121 H12B 109.5 . . ? H12A C121 H12B 109.5 . . ? O12 C121 H12C 109.5 . . ? H12A C121 H12C 109.5 . . ? H12B C121 H12C 109.5 . . ? C14 C13 C12 119.46(17) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C15 C14 C13 120.96(17) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 119.30(18) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C11 C16 C15 120.86(17) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N S2 0.88(2) 2.41(2) 3.2843(15) 169.5(17) 3_666 C121 H12B O1 0.98 2.64 3.274(2) 122.5 3_756 C121 H12A O12 0.98 2.69 3.338(2) 123.8 3_766 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.29 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.283 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.052 _iucr_refine_instructions_details ; TITL IM13 in P2(1)/n CELL 0.71073 11.6420 4.6349 18.8292 90.000 95.453 90.000 ZERR 4.00 0.0009 0.0004 0.0018 0.000 0.005 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 40 40 8 8 4 TEMP -182 SIZE 0.10 0.16 0.45 L.S. 12 BOND $H FMAP 2 PLAN 10 acta mpla 6 c11 c12 c13 c14 c15 c16 c6 o12 c121 mpla 5 c2 o1 c5 n3 n4 s2 c6 eqiv $1 1-x,1-y,1-z eqiv $2 2-x,-y,1-z eqiv $3 2-x,1-y,1-z eqiv $4 1/2+x,1/2-y,1/2+z htab n3 s2_$1 htab c121 o1_$2 htab C121 O12_$3 WGHT 0.028600 0.572400 FVAR 0.25268 O1 4 0.749143 0.111354 0.562465 11.00000 0.01630 0.01856 = 0.01575 -0.00062 -0.00015 0.00312 C2 1 0.659912 0.253317 0.524573 11.00000 0.01268 0.01821 = 0.01879 0.00212 0.00207 0.00067 S2 5 0.608770 0.161632 0.442677 11.00000 0.01749 0.02771 = 0.01688 -0.00438 -0.00177 0.00442 N3 3 0.631600 0.463335 0.567677 11.00000 0.01663 0.02041 = 0.01952 -0.00344 -0.00439 0.00623 H3N 2 0.571899 0.580768 0.561528 11.00000 -1.20000 N4 3 0.699472 0.464749 0.632389 11.00000 0.01763 0.02321 = 0.01718 -0.00243 -0.00363 0.00402 C5 1 0.768521 0.251579 0.626846 11.00000 0.01546 0.01476 = 0.01397 0.00067 0.00397 -0.00334 C6 1 0.860363 0.141554 0.680623 11.00000 0.01759 0.01613 = 0.01522 0.00302 0.00151 0.00030 AFIX 23 H6A 2 0.895434 -0.033348 0.661590 11.00000 -1.20000 H6B 2 0.825143 0.086067 0.724466 11.00000 -1.20000 AFIX 0 C11 1 0.953808 0.363255 0.699309 11.00000 0.01341 0.01294 = 0.01754 0.00342 -0.00311 0.00321 C12 1 1.032697 0.428360 0.649872 11.00000 0.01634 0.01706 = 0.01729 0.00265 -0.00220 0.00422 O12 4 1.017503 0.277253 0.587047 11.00000 0.02016 0.02415 = 0.01741 0.00041 0.00592 0.00082 C121 1 1.107869 0.296310 0.540546 11.00000 0.02429 0.04080 = 0.02400 0.00588 0.01084 0.00709 AFIX 137 H12A 2 1.114483 0.495909 0.524252 11.00000 -1.50000 H12B 2 1.089857 0.169900 0.499267 11.00000 -1.50000 H12C 2 1.181026 0.236145 0.566340 11.00000 -1.50000 AFIX 0 C13 1 1.118449 0.633162 0.665996 11.00000 0.01502 0.02161 = 0.03117 0.00884 -0.00053 0.00180 AFIX 43 H13 2 1.171964 0.677114 0.632486 11.00000 -1.20000 AFIX 0 C14 1 1.125231 0.772611 0.731311 11.00000 0.02059 0.01666 = 0.03716 0.00320 -0.01211 -0.00101 AFIX 43 H14 2 1.182747 0.915633 0.741966 11.00000 -1.20000 AFIX 0 C15 1 1.049530 0.706717 0.781224 11.00000 0.02960 0.01700 = 0.02334 -0.00211 -0.01062 0.00491 AFIX 43 H15 2 1.055844 0.800744 0.826258 11.00000 -1.20000 AFIX 0 C16 1 0.963993 0.501245 0.764817 11.00000 0.02153 0.01790 = 0.01680 0.00173 -0.00179 0.00547 AFIX 43 H16 2 0.911895 0.455025 0.799010 11.00000 -1.20000 HKLF 4 REM IM13 in P2(1)/n REM R1 = 0.0335 for 1662 Fo > 4sig(Fo) and 0.0457 for all 2046 data REM 140 parameters refined using 0 restraints END ; _database_code_depnum_ccdc_archive 'CCDC 964316' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-(3-methoxybenzyl)-1,3,4-thiadiazole-2(3H)-thione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N2 O2 S' _chemical_formula_sum 'C10 H10 N2 O2 S' _chemical_formula_weight 222.26 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n ' _symmetry_space_group_name_Hall '-P 2yn ' 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' _cell_length_a 8.6916(7) _cell_length_b 13.2144(11) _cell_length_c 8.9458(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.960(4) _cell_angle_gamma 90.00 _cell_volume 1025.01(14) _cell_formula_units_Z 4 _cell_measurement_temperature 91(2) _cell_measurement_reflns_used 8417 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 29.40 _exptl_crystal_description 'irregular block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.57 _exptl_crystal_size_min 0.53 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.296 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6011 _exptl_absorpt_correction_T_max 0.7459 _exptl_absorpt_process_details 'SADABS (Bruker, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 91(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13586 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0343 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 29.47 _reflns_number_total 2825 _reflns_number_gt 2442 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'APEX2 and SAINT (Bruker, 2011)' _computing_data_reduction 'SAINT (Bruker, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement ; SHELXL-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999) ; _computing_molecular_graphics ; Mercury (Macrae et al., 2008) ; _computing_publication_material ; SHELXL-97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009), PublCIF (Westrip 2010) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0378P)^2^+0.5661P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2825 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0479 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.0993 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.22792(11) 0.21513(8) 0.60398(11) 0.0214(2) Uani 1 1 d . . . C2 C 0.15828(16) 0.12890(11) 0.54919(15) 0.0213(3) Uani 1 1 d . . . S2 S 0.23125(4) 0.05667(3) 0.42024(4) 0.02461(11) Uani 1 1 d . . . N3 N 0.02994(15) 0.12082(10) 0.62033(14) 0.0233(3) Uani 1 1 d . . . HN3 H -0.035(2) 0.0731(15) 0.610(2) 0.028 Uiso 1 1 d . . . N4 N 0.01154(15) 0.19965(10) 0.71963(14) 0.0240(3) Uani 1 1 d . . . C5 C 0.13218(16) 0.25381(11) 0.70611(15) 0.0215(3) Uani 1 1 d . . . C6 C 0.17948(17) 0.34783(11) 0.78762(16) 0.0234(3) Uani 1 1 d . . . H6A H 0.2821 0.3370 0.8403 0.028 Uiso 1 1 calc R . . H6B H 0.1054 0.3616 0.8643 0.028 Uiso 1 1 calc R . . C11 C 0.18732(16) 0.43991(11) 0.68660(15) 0.0204(3) Uani 1 1 d . . . C12 C 0.08756(16) 0.52083(11) 0.70638(15) 0.0200(3) Uani 1 1 d . . . H112 H 0.0152 0.5176 0.7811 0.024 Uiso 1 1 calc R . . C13 C 0.09442(15) 0.60635(11) 0.61626(15) 0.0197(3) Uani 1 1 d . . . O13 O 0.00370(12) 0.69039(8) 0.62977(11) 0.0232(2) Uani 1 1 d . . . C131 C -0.10385(18) 0.68820(12) 0.74350(17) 0.0276(3) Uani 1 1 d . . . H13A H -0.1754 0.6315 0.7249 0.041 Uiso 1 1 calc R . . H13B H -0.1619 0.7518 0.7419 0.041 Uiso 1 1 calc R . . H13C H -0.0481 0.6797 0.8417 0.041 Uiso 1 1 calc R . . C14 C 0.19927(16) 0.61086(11) 0.50559(16) 0.0218(3) Uani 1 1 d . . . H14 H 0.2032 0.6689 0.4433 0.026 Uiso 1 1 calc R . . C15 C 0.29764(16) 0.53032(12) 0.48695(16) 0.0234(3) Uani 1 1 d . . . H15 H 0.3691 0.5334 0.4114 0.028 Uiso 1 1 calc R . . C16 C 0.29335(16) 0.44502(11) 0.57726(16) 0.0232(3) Uani 1 1 d . . . H16 H 0.3624 0.3905 0.5644 0.028 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 O1 0.0249(5) 0.0164(5) 0.0228(5) -0.0018(4) -0.0003(4) 0.0009(4) C2 0.0265(7) 0.0159(7) 0.0209(6) 0.0011(5) -0.0027(5) 0.0012(5) S2 0.0294(2) 0.0196(2) 0.0249(2) -0.00371(13) 0.00274(14) -0.00006(13) N3 0.0276(6) 0.0158(6) 0.0265(6) -0.0025(5) 0.0021(5) -0.0011(5) N4 0.0299(6) 0.0173(6) 0.0248(6) -0.0012(5) 0.0019(5) 0.0018(5) C5 0.0261(7) 0.0178(7) 0.0202(6) 0.0015(5) -0.0006(5) 0.0044(5) C6 0.0306(7) 0.0169(7) 0.0223(7) -0.0004(5) -0.0007(5) 0.0014(5) C11 0.0235(7) 0.0160(7) 0.0208(6) -0.0018(5) -0.0035(5) -0.0017(5) C12 0.0218(6) 0.0178(7) 0.0199(6) -0.0017(5) -0.0009(5) -0.0014(5) C13 0.0207(6) 0.0161(7) 0.0217(6) -0.0020(5) -0.0031(5) 0.0001(5) O13 0.0265(5) 0.0183(5) 0.0250(5) 0.0021(4) 0.0034(4) 0.0033(4) C131 0.0304(7) 0.0245(8) 0.0283(7) 0.0021(6) 0.0063(6) 0.0064(6) C14 0.0229(7) 0.0201(7) 0.0221(6) 0.0015(5) -0.0012(5) -0.0029(5) C15 0.0219(7) 0.0250(8) 0.0233(7) -0.0017(5) 0.0015(5) -0.0026(5) C16 0.0225(7) 0.0199(7) 0.0270(7) -0.0036(5) -0.0008(5) 0.0009(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.3652(17) . ? O1 C5 1.3760(17) . ? C2 N3 1.3262(19) . ? C2 S2 1.6568(15) . ? N3 N4 1.3854(17) . ? N3 HN3 0.85(2) . ? N4 C5 1.2821(19) . ? C5 C6 1.484(2) . ? C6 C11 1.520(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C11 C16 1.391(2) . ? C11 C12 1.3956(19) . ? C12 C13 1.392(2) . ? C12 H112 0.9500 . ? C13 O13 1.3723(17) . ? C13 C14 1.392(2) . ? O13 C131 1.4287(18) . ? C131 H13A 0.9800 . ? C131 H13B 0.9800 . ? C131 H13C 0.9800 . ? C14 C15 1.382(2) . ? C14 H14 0.9500 . ? C15 C16 1.389(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C5 105.96(11) . . ? N3 C2 O1 105.17(12) . . ? N3 C2 S2 131.51(12) . . ? O1 C2 S2 123.32(11) . . ? C2 N3 N4 112.66(12) . . ? C2 N3 HN3 125.5(13) . . ? N4 N3 HN3 121.9(13) . . ? C5 N4 N3 103.17(12) . . ? N4 C5 O1 113.04(13) . . ? N4 C5 C6 128.43(13) . . ? O1 C5 C6 118.52(12) . . ? C5 C6 C11 113.60(12) . . ? C5 C6 H6A 108.8 . . ? C11 C6 H6A 108.8 . . ? C5 C6 H6B 108.8 . . ? C11 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C16 C11 C12 119.97(13) . . ? C16 C11 C6 121.06(13) . . ? C12 C11 C6 118.96(13) . . ? C13 C12 C11 119.79(13) . . ? C13 C12 H112 120.1 . . ? C11 C12 H112 120.1 . . ? O13 C13 C12 123.94(13) . . ? O13 C13 C14 115.86(12) . . ? C12 C13 C14 120.20(13) . . ? C13 O13 C131 117.03(11) . . ? O13 C131 H13A 109.5 . . ? O13 C131 H13B 109.5 . . ? H13A C131 H13B 109.5 . . ? O13 C131 H13C 109.5 . . ? H13A C131 H13C 109.5 . . ? H13B C131 H13C 109.5 . . ? C15 C14 C13 119.56(13) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 120.86(14) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 119.61(13) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C6 H6A O13 0.99 2.69 3.4894(18) 138.3 2_546 N3 HN3 S2 0.85(2) 2.42(2) 3.2668(14) 176.8(17) 3_556 C131 H13B S2 0.98 2.96 3.8098(16) 145.9 3_566 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 29.47 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.349 _refine_diff_density_min -0.304 _refine_diff_density_rms 0.059 _iucr_refine_instructions_details ; TITL im14 in P2(1)/n CELL 0.71073 8.6916 13.2144 8.9458 90.000 93.960 90.000 ZERR 4.00 0.0007 0.0011 0.0007 0.000 0.004 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 40 40 8 8 4 TEMP -182 SIZE 0.530 0.570 0.600 L.S. 12 BOND $H acta FMAP 2 PLAN 10 eqiv $1 1/2-x,-1/2+y,1.5-z eqiv $2 -x,-y,1-z eqiv $3 -x,1-y,1-z htab c3 o6_$1 htab n2 s1_$2 htab c61 s1_$3 mpla 5 c1 o1 c2 n1 n2 s1 c3 mpla 6 c4 c5 c6 c7 c8 c9 o6 c61 c3 WGHT 0.037800 0.566100 FVAR 0.21012 O1 4 0.227919 0.215126 0.603983 11.00000 0.02492 0.01636 = 0.02279 -0.00181 -0.00029 0.00086 C2 1 0.158283 0.128900 0.549193 11.00000 0.02645 0.01594 = 0.02088 0.00108 -0.00266 0.00117 S2 5 0.231247 0.056668 0.420238 11.00000 0.02943 0.01964 = 0.02486 -0.00371 0.00274 -0.00006 N3 3 0.029935 0.120819 0.620331 11.00000 0.02765 0.01576 = 0.02647 -0.00249 0.00212 -0.00114 HN3 2 -0.034802 0.073052 0.609648 11.00000 -1.20000 N4 3 0.011539 0.199645 0.719634 11.00000 0.02990 0.01733 = 0.02479 -0.00115 0.00188 0.00181 C5 1 0.132178 0.253807 0.706105 11.00000 0.02606 0.01784 = 0.02024 0.00150 -0.00062 0.00443 C6 1 0.179482 0.347827 0.787618 11.00000 0.03062 0.01689 = 0.02225 -0.00035 -0.00075 0.00141 AFIX 23 H6A 2 0.282083 0.337006 0.840347 11.00000 -1.20000 H6B 2 0.105372 0.361597 0.864337 11.00000 -1.20000 AFIX 0 C11 1 0.187318 0.439907 0.686600 11.00000 0.02355 0.01605 = 0.02078 -0.00176 -0.00347 -0.00169 C12 1 0.087564 0.520826 0.706382 11.00000 0.02181 0.01780 = 0.01993 -0.00174 -0.00087 -0.00135 AFIX 43 H112 2 0.015209 0.517550 0.781123 11.00000 -1.20000 AFIX 0 C13 1 0.094422 0.606346 0.616256 11.00000 0.02072 0.01609 = 0.02167 -0.00197 -0.00306 0.00007 O13 4 0.003696 0.690395 0.629767 11.00000 0.02651 0.01830 = 0.02495 0.00210 0.00335 0.00335 C131 1 -0.103852 0.688196 0.743502 11.00000 0.03044 0.02455 = 0.02826 0.00206 0.00626 0.00642 AFIX 137 H13A 2 -0.175359 0.631525 0.724939 11.00000 -1.50000 H13B 2 -0.161880 0.751818 0.741874 11.00000 -1.50000 H13C 2 -0.048089 0.679737 0.841708 11.00000 -1.50000 AFIX 0 C14 1 0.199275 0.610861 0.505591 11.00000 0.02293 0.02008 = 0.02205 0.00149 -0.00122 -0.00293 AFIX 43 H14 2 0.203195 0.668905 0.443312 11.00000 -1.20000 AFIX 0 C15 1 0.297636 0.530318 0.486947 11.00000 0.02187 0.02500 = 0.02335 -0.00174 0.00155 -0.00257 AFIX 43 H15 2 0.369094 0.533357 0.411368 11.00000 -1.20000 AFIX 0 C16 1 0.293350 0.445016 0.577264 11.00000 0.02245 0.01990 = 0.02698 -0.00356 -0.00083 0.00086 AFIX 43 H16 2 0.362426 0.390478 0.564449 11.00000 -1.20000 HKLF 4 REM im14 in P2(1)/n REM R1 = 0.0398 for 2442 Fo > 4sig(Fo) and 0.0479 for all 2825 data REM 140 parameters refined using 0 restraints END ; _database_code_depnum_ccdc_archive 'CCDC 964317' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound3 _audit_creation_method SHELXL-2013 _chemical_name_systematic ; 5-(4-methoxybenzyl)-1,3,4-thiadiazole-2(3H)-thione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 N2 O2 S' _chemical_formula_sum 'C10 H10 N2 O2 S' _chemical_formula_weight 222.26 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' N N 0.0061 0.0033 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_operation_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' _cell_length_a 7.5365(3) _cell_length_b 5.5019(3) _cell_length_c 24.9737(12) _cell_angle_alpha 90 _cell_angle_beta 92.956(2) _cell_angle_gamma 90 _cell_volume 1034.16(9) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 8063 _cell_measurement_theta_min 2.71 _cell_measurement_theta_max 34.62 _exptl_crystal_description 'square plate' _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.428 _exptl_crystal_F_000 464 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.14 _exptl_absorpt_coefficient_mu 0.293 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7164 _exptl_absorpt_correction_T_max 0.7469 _exptl_absorpt_process_details 'SADABS (Bruker, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_number 23676 _diffrn_reflns_av_unetI/netI 0.0264 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.786 _diffrn_reflns_theta_max 34.846 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_point_group_measured_fraction_full 0.999 _reflns_number_total 4485 _reflns_number_gt 3962 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. ; _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'APEX2 and SAINT (Bruker, 2011)' _computing_data_reduction 'SAINT (Bruker, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement ; SHELXL-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999) ; _computing_molecular_graphics ; Mercury (Macrae et al., 2008) ; _computing_publication_material ; SHELXL-97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009), PublCIF (Westrip 2010) ; _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0362P)^2^+0.4376P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 4485 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.63719(9) -0.00313(13) 0.42102(3) 0.01836(13) Uani 1 1 d . . . . . C2 C 0.55894(13) -0.18797(17) 0.44752(4) 0.01759(15) Uani 1 1 d . . . . . S2 S 0.34019(3) -0.21764(5) 0.45092(2) 0.01964(6) Uani 1 1 d . . . . . N3 N 0.69222(11) -0.32149(16) 0.46826(3) 0.01998(15) Uani 1 1 d . . . . . H3N H 0.6806(19) -0.448(3) 0.4901(6) 0.024 Uiso 1 1 d . U . . . N4 N 0.85715(11) -0.22476(16) 0.45792(3) 0.02026(15) Uani 1 1 d . . . . . C5 C 0.81757(12) -0.03490(17) 0.42978(4) 0.01771(15) Uani 1 1 d . . . . . C6 C 0.93926(13) 0.14339(17) 0.40652(4) 0.01904(16) Uani 1 1 d . . . . . H6A H 1.0587 0.1266 0.4246 0.023 Uiso 1 1 calc R U . . . H6B H 0.8959 0.3097 0.4135 0.023 Uiso 1 1 calc R U . . . C11 C 0.95443(11) 0.11092(16) 0.34660(4) 0.01549(15) Uani 1 1 d . . . . . C12 C 0.88509(12) 0.28323(16) 0.31022(4) 0.01657(15) Uani 1 1 d . . . . . H12 H 0.8217 0.4190 0.3230 0.020 Uiso 1 1 calc R U . . . C13 C 0.90751(12) 0.25884(16) 0.25565(4) 0.01647(15) Uani 1 1 d . . . . . H13 H 0.8599 0.3775 0.2313 0.020 Uiso 1 1 calc R U . . . C14 C 1.00009(11) 0.05979(16) 0.23660(3) 0.01496(14) Uani 1 1 d . . . . . O14 O 1.01548(9) 0.05105(13) 0.18237(3) 0.01894(13) Uani 1 1 d . . . . . C141 C 1.10998(14) -0.15197(19) 0.16229(4) 0.02276(18) Uani 1 1 d . . . . . H14A H 1.2317 -0.1523 0.1781 0.034 Uiso 1 1 calc R U . . . H14B H 1.1128 -0.1399 0.1232 0.034 Uiso 1 1 calc R U . . . H14C H 1.0502 -0.3029 0.1718 0.034 Uiso 1 1 calc R U . . . C15 C 1.06889(12) -0.11489(16) 0.27236(4) 0.01641(15) Uani 1 1 d . . . . . H15 H 1.1314 -0.2513 0.2596 0.020 Uiso 1 1 calc R U . . . C16 C 1.04527(12) -0.08791(16) 0.32693(4) 0.01711(15) Uani 1 1 d . . . . . H16 H 1.0920 -0.2074 0.3512 0.021 Uiso 1 1 calc R U . . . 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 O1 0.0190(3) 0.0199(3) 0.0163(3) 0.0022(2) 0.0021(2) 0.0025(2) C2 0.0208(4) 0.0186(4) 0.0135(3) 0.0000(3) 0.0023(3) 0.0024(3) S2 0.01809(11) 0.02348(11) 0.01736(11) 0.00134(8) 0.00098(8) 0.00201(8) N3 0.0191(3) 0.0199(3) 0.0213(4) 0.0044(3) 0.0044(3) 0.0038(3) N4 0.0186(3) 0.0206(4) 0.0220(4) 0.0028(3) 0.0050(3) 0.0025(3) C5 0.0186(4) 0.0196(4) 0.0152(4) -0.0008(3) 0.0029(3) 0.0028(3) C6 0.0216(4) 0.0185(4) 0.0172(4) -0.0013(3) 0.0026(3) -0.0003(3) C11 0.0144(3) 0.0145(3) 0.0176(4) 0.0001(3) 0.0021(3) -0.0005(3) C12 0.0148(3) 0.0144(3) 0.0207(4) 0.0002(3) 0.0029(3) 0.0012(3) C13 0.0149(3) 0.0152(3) 0.0194(4) 0.0035(3) 0.0020(3) 0.0013(3) C14 0.0127(3) 0.0162(3) 0.0161(3) 0.0010(3) 0.0019(3) -0.0009(3) O14 0.0200(3) 0.0211(3) 0.0160(3) 0.0018(2) 0.0035(2) 0.0021(2) C141 0.0269(4) 0.0224(4) 0.0194(4) -0.0018(3) 0.0053(3) 0.0019(3) C15 0.0163(3) 0.0149(3) 0.0180(4) -0.0001(3) 0.0009(3) 0.0021(3) C16 0.0190(4) 0.0148(3) 0.0176(4) 0.0013(3) 0.0004(3) 0.0018(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.3639(11) . ? O1 C5 1.3769(11) . ? C2 N3 1.3278(12) . ? C2 S2 1.6632(10) . ? N3 N4 1.3886(12) . ? N3 H3N 0.892(15) . ? N4 C5 1.2855(12) . ? C5 C6 1.4818(13) . ? C6 C11 1.5172(13) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C11 C16 1.3934(12) . ? C11 C12 1.3959(12) . ? C12 C13 1.3883(13) . ? C12 H12 0.9500 . ? C13 C14 1.3953(12) . ? C13 H13 0.9500 . ? C14 O14 1.3659(11) . ? C14 C15 1.3937(12) . ? O14 C141 1.4294(12) . ? C141 H14A 0.9800 . ? C141 H14B 0.9800 . ? C141 H14C 0.9800 . ? C15 C16 1.3913(12) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C5 106.04(7) . . ? N3 C2 O1 105.34(8) . . ? N3 C2 S2 131.12(8) . . ? O1 C2 S2 123.54(7) . . ? C2 N3 N4 112.45(8) . . ? C2 N3 H3N 125.0(9) . . ? N4 N3 H3N 122.0(9) . . ? C5 N4 N3 103.20(8) . . ? N4 C5 O1 112.92(8) . . ? N4 C5 C6 128.42(9) . . ? O1 C5 C6 118.66(8) . . ? C5 C6 C11 112.85(8) . . ? C5 C6 H6A 109.0 . . ? C11 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C11 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C16 C11 C12 118.55(8) . . ? C16 C11 C6 120.24(8) . . ? C12 C11 C6 121.15(8) . . ? C13 C12 C11 120.86(8) . . ? C13 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? C12 C13 C14 119.93(8) . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? O14 C14 C15 124.28(8) . . ? O14 C14 C13 115.80(8) . . ? C15 C14 C13 119.92(8) . . ? C14 O14 C141 116.40(7) . . ? O14 C141 H14A 109.5 . . ? O14 C141 H14B 109.5 . . ? H14A C141 H14B 109.5 . . ? O14 C141 H14C 109.5 . . ? H14A C141 H14C 109.5 . . ? H14B C141 H14C 109.5 . . ? C16 C15 C14 119.47(8) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C11 121.27(8) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N S2 0.892(15) 2.366(15) 3.2579(9) 178.1(13) 3_646 C6 H6A S2 0.99 2.89 3.7363(10) 143.4 1_655 C12 H12 O14 0.95 2.64 3.3730(11) 134.3 2_655 _refine_diff_density_max 0.497 _refine_diff_density_min -0.282 _refine_diff_density_rms 0.062 _iucr_refine_instructions_details ; TITL IM12 in P2(1)/n CELL 0.71073 7.5365 5.5019 24.9737 90.000 92.956 90.000 ZERR 4.00 0.0003 0.0003 0.0012 0.000 0.002 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 40 40 8 8 4 TEMP -180 SIZE 0.14 0.37 0.37 acta L.S. 12 BOND $H FMAP 2 PLAN 5 mpla 5 c2 o1 c5 n3 n4 s2 c6 mpla 6 c11 c12 c13 c14 c15 c16 c6 o14 c141 eqiv $1 1-x,-1-y,1-z eqiv $2 1+x,y,z eqiv $3 1.5-x,1/2+y,1/2-z htab n3 s2_$1 htab c6 s2_$2 htab c12 o14_$3 WGHT 0.036200 0.437600 FVAR 0.20812 O1 4 0.637185 -0.003134 0.421019 11.00000 0.01902 0.01988 = 0.01630 0.00221 0.00206 0.00252 C2 1 0.558942 -0.187968 0.447522 11.00000 0.02076 0.01860 = 0.01354 -0.00005 0.00225 0.00244 S2 5 0.340187 -0.217643 0.450922 11.00000 0.01809 0.02348 = 0.01736 0.00134 0.00098 0.00201 N3 3 0.692217 -0.321487 0.468260 11.00000 0.01911 0.01993 = 0.02126 0.00436 0.00444 0.00383 H3N 2 0.680553 -0.448087 0.490135 11.00000 -1.20000 N4 3 0.857154 -0.224758 0.457922 11.00000 0.01858 0.02064 = 0.02196 0.00282 0.00497 0.00250 C5 1 0.817568 -0.034901 0.429779 11.00000 0.01859 0.01958 = 0.01517 -0.00076 0.00294 0.00275 C6 1 0.939260 0.143390 0.406517 11.00000 0.02162 0.01850 = 0.01717 -0.00133 0.00261 -0.00034 AFIX 23 H6A 2 1.058654 0.126609 0.424595 11.00000 -1.20000 H6B 2 0.895947 0.309661 0.413541 11.00000 -1.20000 AFIX 0 C11 1 0.954426 0.110919 0.346599 11.00000 0.01445 0.01452 = 0.01765 0.00014 0.00214 -0.00051 C12 1 0.885093 0.283229 0.310215 11.00000 0.01478 0.01440 = 0.02073 0.00018 0.00290 0.00116 AFIX 43 H12 2 0.821744 0.418952 0.322958 11.00000 -1.20000 AFIX 0 C13 1 0.907511 0.258839 0.255646 11.00000 0.01495 0.01518 = 0.01939 0.00347 0.00196 0.00131 AFIX 43 H13 2 0.859870 0.377546 0.231304 11.00000 -1.20000 AFIX 0 C14 1 1.000090 0.059787 0.236595 11.00000 0.01268 0.01619 = 0.01613 0.00101 0.00186 -0.00095 O14 4 1.015476 0.051053 0.182372 11.00000 0.02005 0.02106 = 0.01598 0.00178 0.00352 0.00211 C141 1 1.109975 -0.151968 0.162294 11.00000 0.02687 0.02245 = 0.01937 -0.00179 0.00533 0.00192 AFIX 137 H14A 2 1.231735 -0.152293 0.178093 11.00000 -1.50000 H14B 2 1.112790 -0.139897 0.123196 11.00000 -1.50000 H14C 2 1.050190 -0.302905 0.171827 11.00000 -1.50000 AFIX 0 C15 1 1.068889 -0.114894 0.272361 11.00000 0.01632 0.01493 = 0.01798 -0.00014 0.00093 0.00207 AFIX 43 H15 2 1.131406 -0.251291 0.259583 11.00000 -1.20000 AFIX 0 C16 1 1.045274 -0.087911 0.326927 11.00000 0.01896 0.01476 = 0.01756 0.00131 0.00043 0.00175 AFIX 43 H16 2 1.091991 -0.207352 0.351242 11.00000 -1.20000 AFIX 0 HKLF 4 REM IM12 in P2(1)/n REM R1 = 0.0364 for 3962 Fo > 4sig(Fo) and 0.0423 for all 4485 data REM 140 parameters refined using 0 restraints END WGHT 0.0362 0.4376 REM Highest difference peak 0.497, deepest hole -0.282, 1-sigma level 0.062 Q1 1 0.8944 0.2643 0.2820 11.00000 0.05 0.50 Q2 1 0.9534 0.1619 0.2481 11.00000 0.05 0.49 Q3 1 1.0391 -0.0344 0.2512 11.00000 0.05 0.46 Q4 1 0.9910 0.0183 0.3371 11.00000 0.05 0.44 Q5 1 0.8723 0.0556 0.4173 11.00000 0.05 0.41 ; _database_code_depnum_ccdc_archive 'CCDC 964318' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_compound4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-(2-methoxyphenethyl)-1,3,4-thiadiazole-2(3H)-thione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N2 O2 S' _chemical_formula_sum 'C11 H12 N2 O2 S' _chemical_formula_weight 236.29 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c ' _symmetry_space_group_name_Hall '-P 2ybc ' 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' _cell_length_a 9.8668(8) _cell_length_b 6.9888(6) _cell_length_c 16.1978(13) _cell_angle_alpha 90.00 _cell_angle_beta 98.855(4) _cell_angle_gamma 90.00 _cell_volume 1103.64(16) _cell_formula_units_Z 4 _cell_measurement_temperature 92(2) _cell_measurement_reflns_used 6610 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 31.17 _exptl_crystal_description 'square block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.422 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7079 _exptl_absorpt_correction_T_max 0.7464 _exptl_absorpt_process_details 'SADABS (Bruker, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 92(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26143 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0254 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 32.06 _reflns_number_total 3854 _reflns_number_gt 3271 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'APEX2 and SAINT (Bruker, 2011)' _computing_data_reduction 'SAINT (Bruker, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement ; SHELXL-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999) ; _computing_molecular_graphics ; Mercury (Macrae et al., 2008) ; _computing_publication_material ; SHELXL-97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009), PublCIF (Westrip 2010) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+0.3053P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3854 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0924 _refine_ls_wR_factor_gt 0.0876 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.52218(8) 1.12583(11) 0.64972(5) 0.01534(15) Uani 1 1 d . . . C2 C 0.49998(10) 1.27748(14) 0.59632(6) 0.01322(17) Uani 1 1 d . . . S2 S 0.39110(3) 1.45217(4) 0.609414(16) 0.01688(8) Uani 1 1 d . . . N3 N 0.57852(9) 1.24465(12) 0.53817(5) 0.01400(16) Uani 1 1 d . . . H3N H 0.5918(14) 1.322(2) 0.4985(9) 0.017 Uiso 1 1 d . . . N4 N 0.65155(9) 1.07361(12) 0.55130(5) 0.01436(17) Uani 1 1 d . . . C5 C 0.61478(10) 1.00866(14) 0.61881(6) 0.01345(18) Uani 1 1 d . . . C6 C 0.65521(11) 0.83549(14) 0.66912(6) 0.01504(18) Uani 1 1 d . . . H6A H 0.5710 0.7658 0.6774 0.018 Uiso 1 1 calc R . . H6B H 0.7021 0.8760 0.7248 0.018 Uiso 1 1 calc R . . C7 C 0.74893(10) 0.69772(15) 0.63165(6) 0.01460(18) Uani 1 1 d . . . H7A H 0.7022 0.6536 0.5765 0.018 Uiso 1 1 calc R . . H7B H 0.8336 0.7659 0.6230 0.018 Uiso 1 1 calc R . . C11 C 0.78694(10) 0.52564(14) 0.68741(6) 0.01247(17) Uani 1 1 d . . . C12 C 0.86562(10) 0.37755(14) 0.65959(6) 0.01303(17) Uani 1 1 d . . . O12 O 0.89798(8) 0.40233(11) 0.58085(5) 0.01626(15) Uani 1 1 d . . . C121 C 0.98236(12) 0.25977(17) 0.55041(7) 0.0208(2) Uani 1 1 d . . . H12A H 1.0700 0.2511 0.5880 0.031 Uiso 1 1 calc R . . H12B H 0.9990 0.2951 0.4943 0.031 Uiso 1 1 calc R . . H12C H 0.9357 0.1357 0.5482 0.031 Uiso 1 1 calc R . . C13 C 0.90707(10) 0.22036(15) 0.71013(6) 0.01563(19) Uani 1 1 d . . . H13 H 0.9604 0.1218 0.6906 0.019 Uiso 1 1 calc R . . C14 C 0.86952(11) 0.20878(15) 0.78999(7) 0.01700(19) Uani 1 1 d . . . H14 H 0.8978 0.1023 0.8248 0.020 Uiso 1 1 calc R . . C15 C 0.79142(10) 0.35183(16) 0.81819(6) 0.01680(19) Uani 1 1 d . . . H15 H 0.7655 0.3434 0.8722 0.020 Uiso 1 1 calc R . . C16 C 0.75070(10) 0.50900(15) 0.76691(6) 0.01509(18) Uani 1 1 d . . . H16 H 0.6971 0.6068 0.7867 0.018 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 O1 0.0182(3) 0.0126(3) 0.0165(3) 0.0034(3) 0.0067(3) 0.0038(3) C2 0.0149(4) 0.0111(4) 0.0137(4) 0.0017(3) 0.0026(3) 0.0001(3) S2 0.01975(13) 0.01434(13) 0.01808(13) 0.00398(8) 0.00779(9) 0.00552(9) N3 0.0168(4) 0.0118(4) 0.0140(4) 0.0021(3) 0.0044(3) 0.0019(3) N4 0.0160(4) 0.0112(4) 0.0161(4) 0.0009(3) 0.0033(3) 0.0017(3) C5 0.0135(4) 0.0111(4) 0.0159(4) -0.0004(3) 0.0027(3) 0.0009(3) C6 0.0180(4) 0.0118(4) 0.0159(4) 0.0019(3) 0.0046(3) 0.0024(3) C7 0.0169(4) 0.0123(4) 0.0150(4) 0.0018(3) 0.0039(3) 0.0028(3) C11 0.0122(4) 0.0110(4) 0.0142(4) 0.0008(3) 0.0021(3) 0.0003(3) C12 0.0130(4) 0.0124(4) 0.0138(4) -0.0006(3) 0.0025(3) -0.0002(3) O12 0.0197(4) 0.0154(3) 0.0147(3) 0.0002(3) 0.0060(3) 0.0035(3) C121 0.0223(5) 0.0203(5) 0.0217(5) -0.0021(4) 0.0091(4) 0.0045(4) C13 0.0149(4) 0.0133(4) 0.0187(4) 0.0007(3) 0.0026(3) 0.0021(3) C14 0.0173(4) 0.0151(5) 0.0185(4) 0.0045(4) 0.0023(4) 0.0013(4) C15 0.0168(4) 0.0182(5) 0.0160(4) 0.0032(4) 0.0047(4) 0.0000(4) C16 0.0148(4) 0.0144(4) 0.0168(4) 0.0013(3) 0.0046(3) 0.0016(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.3641(12) . ? O1 C5 1.3772(12) . ? C2 N3 1.3285(12) . ? C2 S2 1.6612(10) . ? N3 N4 1.3951(12) . ? N3 H3N 0.863(15) . ? N4 C5 1.2868(13) . ? C5 C6 1.4792(14) . ? C6 C7 1.5242(14) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C11 1.5160(14) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C11 C16 1.3933(13) . ? C11 C12 1.4087(13) . ? C12 O12 1.3726(12) . ? C12 C13 1.3932(14) . ? O12 C121 1.4337(13) . ? C121 H12A 0.9800 . ? C121 H12B 0.9800 . ? C121 H12C 0.9800 . ? C13 C14 1.4017(14) . ? C13 H13 0.9500 . ? C14 C15 1.3822(15) . ? C14 H14 0.9500 . ? C15 C16 1.3983(14) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 O1 C5 106.40(7) . . ? N3 C2 O1 105.13(8) . . ? N3 C2 S2 132.58(8) . . ? O1 C2 S2 122.27(7) . . ? C2 N3 N4 112.58(8) . . ? C2 N3 H3N 126.3(10) . . ? N4 N3 H3N 120.9(10) . . ? C5 N4 N3 103.01(8) . . ? N4 C5 O1 112.88(9) . . ? N4 C5 C6 132.02(9) . . ? O1 C5 C6 115.09(8) . . ? C5 C6 C7 115.23(8) . . ? C5 C6 H6A 108.5 . . ? C7 C6 H6A 108.5 . . ? C5 C6 H6B 108.5 . . ? C7 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C11 C7 C6 111.93(8) . . ? C11 C7 H7A 109.2 . . ? C6 C7 H7A 109.2 . . ? C11 C7 H7B 109.2 . . ? C6 C7 H7B 109.2 . . ? H7A C7 H7B 107.9 . . ? C16 C11 C12 117.82(9) . . ? C16 C11 C7 122.79(9) . . ? C12 C11 C7 119.36(9) . . ? O12 C12 C13 123.79(9) . . ? O12 C12 C11 115.02(9) . . ? C13 C12 C11 121.18(9) . . ? C12 O12 C121 117.54(8) . . ? O12 C121 H12A 109.5 . . ? O12 C121 H12B 109.5 . . ? H12A C121 H12B 109.5 . . ? O12 C121 H12C 109.5 . . ? H12A C121 H12C 109.5 . . ? H12B C121 H12C 109.5 . . ? C12 C13 C14 119.49(9) . . ? C12 C13 H13 120.3 . . ? C14 C13 H13 120.3 . . ? C15 C14 C13 120.22(10) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C14 C15 C16 119.71(9) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 121.57(9) . . ? C11 C16 H16 119.2 . . ? C15 C16 H16 119.2 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N S2 0.863(15) 2.383(15) 3.2427(9) 174.7(13) 3_686 C6 H6A S2 0.99 2.93 3.7586(11) 142.2 1_545 C16 H16 O1 0.95 2.54 3.2954(12) 136.8 2_646 C121 H12B O12 0.98 2.71 3.5021(14) 137.7 3_766 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 32.06 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.497 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.060 _iucr_refine_instructions_details ; TITL IM11 in P2(1)/c CELL 0.71073 9.8668 6.9888 16.1978 90.000 98.855 90.000 ZERR 4.00 0.0008 0.0006 0.0013 0.000 0.004 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O S UNIT 44 48 8 8 4 TEMP -181 SIZE 0.180 0.180 0.250 L.S. 12 BOND $H FMAP 2 PLAN 10 eqiv $1 1-x,3-y,1-z eqiv $2 x,-1+y,z eqiv $3 1-x,-1/2+y,1.5-z eqiv $4 2-x,1-y,1-z htab N3 S2_$1 htab C6 S2_$2 htab C16 O1_$3 htab C121 O12_$4 mpla s1 c2 o1 c5 n2 n3 c6 c7 c11 c12 o13 c121 c13 c14 c15 c16 mpla 5 c2 o1 c5 n3 n4 S2 c6 mpla 6 c11 c12 c13 c14 c15 c16 o12 c121 c7 mpla c5 c6 c7 c11 mpla 5 c2 o1 c5 n3 n4 S2 c6 ACTA WGHT 0.046600 0.305300 FVAR 0.20522 O1 4 0.522181 1.125832 0.649717 11.00000 0.01818 0.01256 = 0.01654 0.00343 0.00669 0.00375 C2 1 0.499977 1.277480 0.596323 11.00000 0.01490 0.01114 = 0.01373 0.00175 0.00256 0.00012 S2 5 0.391105 1.452170 0.609414 11.00000 0.01975 0.01434 = 0.01808 0.00398 0.00779 0.00552 N3 3 0.578515 1.244652 0.538174 11.00000 0.01683 0.01181 = 0.01400 0.00209 0.00441 0.00188 H3N 2 0.591765 1.321597 0.498539 11.00000 -1.20000 N4 3 0.651550 1.073615 0.551300 11.00000 0.01597 0.01123 = 0.01615 0.00087 0.00329 0.00166 C5 1 0.614781 1.008665 0.618814 11.00000 0.01346 0.01114 = 0.01588 -0.00042 0.00270 0.00093 C6 1 0.655215 0.835486 0.669122 11.00000 0.01803 0.01179 = 0.01593 0.00190 0.00462 0.00235 AFIX 23 H6A 2 0.571014 0.765799 0.677449 11.00000 -1.20000 H6B 2 0.702091 0.875997 0.724841 11.00000 -1.20000 AFIX 0 C7 1 0.748926 0.697723 0.631651 11.00000 0.01693 0.01233 = 0.01500 0.00182 0.00394 0.00280 AFIX 23 H7A 2 0.702174 0.653642 0.576453 11.00000 -1.20000 H7B 2 0.833569 0.765868 0.622983 11.00000 -1.20000 AFIX 0 C11 1 0.786945 0.525645 0.687407 11.00000 0.01217 0.01103 = 0.01423 0.00081 0.00209 0.00033 C12 1 0.865617 0.377553 0.659591 11.00000 0.01301 0.01245 = 0.01377 -0.00063 0.00254 -0.00020 O12 4 0.897977 0.402326 0.580852 11.00000 0.01965 0.01543 = 0.01474 0.00020 0.00596 0.00349 C121 1 0.982361 0.259765 0.550413 11.00000 0.02226 0.02031 = 0.02174 -0.00213 0.00905 0.00453 AFIX 137 H12A 2 1.070046 0.251101 0.587981 11.00000 -1.50000 H12B 2 0.999034 0.295072 0.494290 11.00000 -1.50000 H12C 2 0.935684 0.135673 0.548162 11.00000 -1.50000 AFIX 0 C13 1 0.907074 0.220365 0.710126 11.00000 0.01491 0.01329 = 0.01870 0.00073 0.00265 0.00210 AFIX 43 H13 2 0.960387 0.121787 0.690607 11.00000 -1.20000 AFIX 0 C14 1 0.869519 0.208781 0.789989 11.00000 0.01726 0.01509 = 0.01851 0.00451 0.00226 0.00131 AFIX 43 H14 2 0.897842 0.102258 0.824844 11.00000 -1.20000 AFIX 0 C15 1 0.791418 0.351829 0.818193 11.00000 0.01682 0.01823 = 0.01601 0.00324 0.00467 0.00002 AFIX 43 H15 2 0.765513 0.343406 0.872187 11.00000 -1.20000 AFIX 0 C16 1 0.750701 0.508999 0.766907 11.00000 0.01478 0.01437 = 0.01680 0.00127 0.00460 0.00159 AFIX 43 H16 2 0.697052 0.606754 0.786739 11.00000 -1.20000 HKLF 4 REM IM11 in P2(1)/c REM R1 = 0.0335 for 3271 Fo > 4sig(Fo) and 0.0407 for all 3854 data REM 149 parameters refined using 0 restraints END ; _database_code_depnum_ccdc_archive 'CCDC 964319' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_Compound5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-(4-methoxyphenethyl)-1,3,4-thiadiazole-2(3H)-thione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N2 O2 S' _chemical_formula_sum 'C11 H12 N2 O2 S' _chemical_formula_weight 236.29 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' N N 0.0061 0.0033 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8075(8) _cell_length_b 11.2905(13) _cell_length_c 13.2898(18) _cell_angle_alpha 88.359(7) _cell_angle_beta 80.741(6) _cell_angle_gamma 73.514(6) _cell_volume 1108.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 92(2) _cell_measurement_reflns_used 3312 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 24.40 _exptl_crystal_description 'irregular block' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 496 _exptl_absorpt_coefficient_mu 0.278 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6645 _exptl_absorpt_correction_T_max 0.7451 _exptl_absorpt_process_details 'SADABS (Bruker, 2011)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 92(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16904 _diffrn_reflns_av_R_equivalents 0.0439 _diffrn_reflns_av_sigmaI/netI 0.0423 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 24.76 _reflns_number_total 3699 _reflns_number_gt 2673 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'APEX2 (Bruker, 2011)' _computing_cell_refinement 'APEX2 and SAINT (Bruker, 2011)' _computing_data_reduction 'SAINT (Bruker, 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement ; SHELXL-97 (Sheldrick, 2008) & TITAN (Hunter & Simpson, 1999) ; _computing_molecular_graphics ; Mercury (Macrae et al., 2008) ; _computing_publication_material ; SHELXL-97, enCIFer (Allen et al., 2004), PLATON (Spek, 2009), PublCIF (Westrip 2010) ; _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1146P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3699 _refine_ls_number_parameters 297 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0788 _refine_ls_R_factor_gt 0.0566 _refine_ls_wR_factor_ref 0.1733 _refine_ls_wR_factor_gt 0.1502 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group O1A O 0.9136(2) -0.21662(16) 0.35667(14) 0.0157(5) Uani 1 1 d . . . C2A C 1.0025(3) -0.3391(2) 0.36781(19) 0.0156(6) Uani 1 1 d . . . S2A S 1.22437(9) -0.39416(7) 0.35474(5) 0.0204(3) Uani 1 1 d . . . N3A N 0.8711(3) -0.3944(2) 0.38979(18) 0.0178(6) Uani 1 1 d . . . H3NA H 0.883(4) -0.471(3) 0.394(2) 0.021 Uiso 1 1 d . . . N4A N 0.6984(3) -0.31279(19) 0.39159(16) 0.0164(5) Uani 1 1 d . . . C5A C 0.7312(3) -0.2083(2) 0.3723(2) 0.0146(6) Uani 1 1 d . . . C6A C 0.6022(3) -0.0859(2) 0.3655(2) 0.0173(6) Uani 1 1 d . . . H6A H 0.6277 -0.0525 0.2967 0.021 Uiso 1 1 calc R . . H6B H 0.6183 -0.0288 0.4160 0.021 Uiso 1 1 calc R . . C7A C 0.4065(3) -0.0925(2) 0.3852(2) 0.0165(6) Uani 1 1 d . . . H7A H 0.3929 -0.1509 0.3349 0.020 Uiso 1 1 calc R . . H7B H 0.3833 -0.1269 0.4538 0.020 Uiso 1 1 calc R . . C11A C 0.2627(4) 0.0303(2) 0.37941(19) 0.0147(6) Uani 1 1 d . . . C12A C 0.2976(3) 0.1448(2) 0.37677(19) 0.0146(6) Uani 1 1 d . . . H12A H 0.4181 0.1481 0.3758 0.018 Uiso 1 1 calc R . . C13A C 0.1598(3) 0.2547(2) 0.3755(2) 0.0152(6) Uani 1 1 d . . . H13A H 0.1866 0.3318 0.3733 0.018 Uiso 1 1 calc R . . C14A C -0.0166(3) 0.2509(2) 0.37747(19) 0.0133(6) Uani 1 1 d . . . O14A O -0.1452(2) 0.36354(16) 0.37662(14) 0.0170(5) Uani 1 1 d . . . C141 C -0.3339(4) 0.3664(3) 0.3910(2) 0.0209(7) Uani 1 1 d . . . H14A H -0.3550 0.3191 0.3358 0.031 Uiso 1 1 calc R . . H14B H -0.4090 0.4521 0.3902 0.031 Uiso 1 1 calc R . . H14C H -0.3656 0.3298 0.4566 0.031 Uiso 1 1 calc R . . C15A C -0.0548(3) 0.1371(2) 0.37869(19) 0.0139(6) Uani 1 1 d . . . H15A H -0.1751 0.1337 0.3787 0.017 Uiso 1 1 calc R . . C16A C 0.0841(4) 0.0297(3) 0.37983(19) 0.0163(6) Uani 1 1 d . . . H16A H 0.0572 -0.0473 0.3810 0.020 Uiso 1 1 calc R . . O1B O 1.0305(2) 0.02108(16) 0.86169(13) 0.0164(5) Uani 1 1 d . . . C2B C 1.1218(4) -0.1031(2) 0.8636(2) 0.0161(6) Uani 1 1 d . . . S2B S 1.34353(9) -0.15818(6) 0.84566(5) 0.0203(3) Uani 1 1 d . . . N3B N 0.9900(3) -0.1590(2) 0.88199(18) 0.0186(6) Uani 1 1 d . . . H3B H 1.003(4) -0.234(3) 0.884(2) 0.022 Uiso 1 1 d . . . N4B N 0.8173(3) -0.0775(2) 0.88946(17) 0.0175(6) Uani 1 1 d . . . C5B C 0.8480(3) 0.0288(2) 0.87735(19) 0.0143(6) Uani 1 1 d . . . C6B C 0.7190(3) 0.1517(2) 0.8748(2) 0.0163(6) Uani 1 1 d . . . H6C H 0.7433 0.1885 0.8074 0.020 Uiso 1 1 calc R . . H6D H 0.7365 0.2058 0.9273 0.020 Uiso 1 1 calc R . . C7B C 0.5220(3) 0.1459(3) 0.8943(2) 0.0176(6) Uani 1 1 d . . . H7C H 0.5100 0.0832 0.8475 0.021 Uiso 1 1 calc R . . H7D H 0.4949 0.1179 0.9649 0.021 Uiso 1 1 calc R . . C11B C 0.3822(3) 0.2674(2) 0.8805(2) 0.0159(6) Uani 1 1 d . . . C12B C 0.4216(4) 0.3803(2) 0.8648(2) 0.0179(6) Uani 1 1 d . . . H12B H 0.5434 0.3826 0.8596 0.021 Uiso 1 1 calc R . . C13B C 0.2865(4) 0.4896(2) 0.8566(2) 0.0190(7) Uani 1 1 d . . . H13B H 0.3164 0.5654 0.8462 0.023 Uiso 1 1 calc R . . C14B C 0.1077(4) 0.4877(2) 0.8638(2) 0.0163(6) Uani 1 1 d . . . O14B O -0.0177(2) 0.59977(16) 0.85603(14) 0.0201(5) Uani 1 1 d . . . C142 C -0.2049(3) 0.6027(3) 0.8666(2) 0.0217(7) Uani 1 1 d . . . H14D H -0.2206 0.5492 0.8142 0.033 Uiso 1 1 calc R . . H14E H -0.2784 0.6876 0.8587 0.033 Uiso 1 1 calc R . . H14F H -0.2432 0.5734 0.9343 0.033 Uiso 1 1 calc R . . C15B C 0.0677(3) 0.3745(2) 0.87710(19) 0.0117(6) Uani 1 1 d . . . H15B H -0.0533 0.3715 0.8795 0.014 Uiso 1 1 calc R . . C16B C 0.2016(4) 0.2681(2) 0.8867(2) 0.0186(7) Uani 1 1 d . . . H16B H 0.1709 0.1927 0.8979 0.022 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 O1A 0.0170(10) 0.0110(10) 0.0190(10) 0.0001(8) -0.0017(8) -0.0041(8) C2A 0.0201(15) 0.0135(15) 0.0129(15) -0.0024(11) -0.0040(11) -0.0031(12) S2A 0.0147(4) 0.0218(5) 0.0236(5) -0.0021(3) -0.0035(3) -0.0030(3) N3A 0.0154(13) 0.0094(12) 0.0270(14) 0.0011(11) -0.0032(10) -0.0013(11) N4A 0.0130(12) 0.0120(13) 0.0224(13) -0.0002(10) -0.0018(10) -0.0011(10) C5A 0.0131(14) 0.0179(16) 0.0131(14) -0.0013(12) -0.0020(11) -0.0049(12) C6A 0.0201(15) 0.0133(15) 0.0189(16) -0.0002(12) -0.0030(12) -0.0052(12) C7A 0.0168(15) 0.0137(15) 0.0183(16) -0.0010(12) -0.0020(11) -0.0037(12) C11A 0.0190(15) 0.0123(15) 0.0121(15) 0.0019(11) -0.0015(11) -0.0041(12) C12A 0.0138(14) 0.0153(15) 0.0144(15) 0.0000(11) 0.0005(11) -0.0051(12) C13A 0.0198(15) 0.0087(14) 0.0185(15) -0.0027(11) -0.0015(11) -0.0069(12) C14A 0.0165(15) 0.0125(15) 0.0094(14) 0.0004(11) -0.0009(11) -0.0024(12) O14A 0.0134(10) 0.0114(10) 0.0236(11) -0.0013(8) -0.0024(8) 0.0005(8) C141 0.0167(15) 0.0221(17) 0.0248(17) -0.0006(13) -0.0053(12) -0.0054(13) C15A 0.0119(14) 0.0179(16) 0.0127(15) 0.0017(12) -0.0022(11) -0.0057(12) C16A 0.0210(15) 0.0155(15) 0.0142(15) 0.0002(12) -0.0016(11) -0.0085(13) O1B 0.0144(10) 0.0133(11) 0.0221(11) 0.0002(8) -0.0042(8) -0.0043(8) C2B 0.0228(15) 0.0105(15) 0.0132(15) 0.0018(11) -0.0037(11) -0.0016(13) S2B 0.0152(4) 0.0218(5) 0.0232(5) 0.0007(3) -0.0043(3) -0.0036(3) N3B 0.0156(13) 0.0140(13) 0.0231(14) 0.0029(11) -0.0001(10) -0.0011(11) N4B 0.0124(12) 0.0154(13) 0.0234(14) 0.0023(10) -0.0016(10) -0.0025(10) C5B 0.0136(14) 0.0167(16) 0.0129(15) -0.0008(11) -0.0015(11) -0.0053(12) C6B 0.0167(15) 0.0134(15) 0.0181(15) -0.0029(12) -0.0007(11) -0.0039(12) C7B 0.0179(15) 0.0158(15) 0.0202(16) 0.0021(12) -0.0042(12) -0.0061(12) C11B 0.0179(15) 0.0150(15) 0.0137(15) -0.0013(12) -0.0007(11) -0.0037(12) C12B 0.0156(15) 0.0181(16) 0.0191(15) 0.0021(12) 0.0017(11) -0.0061(12) C13B 0.0222(16) 0.0125(15) 0.0212(16) 0.0027(12) 0.0011(12) -0.0062(13) C14B 0.0216(15) 0.0115(15) 0.0130(15) 0.0008(11) -0.0012(11) -0.0012(12) O14B 0.0170(10) 0.0144(11) 0.0253(12) 0.0013(8) -0.0008(8) -0.0003(8) C142 0.0148(15) 0.0278(18) 0.0200(16) -0.0003(13) -0.0041(12) -0.0010(13) C15B 0.0146(14) 0.0103(15) 0.0136(14) 0.0033(11) -0.0068(11) -0.0068(12) C16B 0.0252(16) 0.0139(15) 0.0181(16) -0.0007(12) -0.0024(12) -0.0082(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1A C2A 1.376(3) . ? O1A C5A 1.382(3) . ? C2A N3A 1.335(3) . ? C2A S2A 1.648(3) . ? N3A N4A 1.398(3) . ? N3A H3NA 0.85(3) . ? N4A C5A 1.287(3) . ? C5A C6A 1.471(4) . ? C6A C7A 1.531(3) . ? C6A H6A 0.9900 . ? C6A H6B 0.9900 . ? C7A C11A 1.525(4) . ? C7A H7A 0.9900 . ? C7A H7B 0.9900 . ? C11A C12A 1.394(4) . ? C11A C16A 1.396(4) . ? C12A C13A 1.394(4) . ? C12A H12A 0.9500 . ? C13A C14A 1.386(3) . ? C13A H13A 0.9500 . ? C14A O14A 1.380(3) . ? C14A C15A 1.399(4) . ? O14A C141 1.446(3) . ? C141 H14A 0.9800 . ? C141 H14B 0.9800 . ? C141 H14C 0.9800 . ? C15A C16A 1.380(4) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? O1B C2B 1.382(3) . ? O1B C5B 1.384(3) . ? C2B N3B 1.340(3) . ? C2B S2B 1.645(3) . ? N3B N4B 1.390(3) . ? N3B H3B 0.82(3) . ? N4B C5B 1.290(3) . ? C5B C6B 1.468(4) . ? C6B C7B 1.538(4) . ? C6B H6C 0.9900 . ? C6B H6D 0.9900 . ? C7B C11B 1.520(4) . ? C7B H7C 0.9900 . ? C7B H7D 0.9900 . ? C11B C12B 1.397(4) . ? C11B C16B 1.397(3) . ? C12B C13B 1.392(4) . ? C12B H12B 0.9500 . ? C13B C14B 1.390(4) . ? C13B H13B 0.9500 . ? C14B O14B 1.376(3) . ? C14B C15B 1.398(4) . ? O14B C142 1.436(3) . ? C142 H14D 0.9800 . ? C142 H14E 0.9800 . ? C142 H14F 0.9800 . ? C15B C16B 1.369(4) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2A O1A C5A 106.14(19) . . ? N3A C2A O1A 104.8(2) . . ? N3A C2A S2A 131.5(2) . . ? O1A C2A S2A 123.73(19) . . ? C2A N3A N4A 112.9(2) . . ? C2A N3A H3NA 127.4(18) . . ? N4A N3A H3NA 119.1(19) . . ? C5A N4A N3A 102.9(2) . . ? N4A C5A O1A 113.3(2) . . ? N4A C5A C6A 128.7(2) . . ? O1A C5A C6A 118.0(2) . . ? C5A C6A C7A 111.4(2) . . ? C5A C6A H6A 109.3 . . ? C7A C6A H6A 109.3 . . ? C5A C6A H6B 109.3 . . ? C7A C6A H6B 109.3 . . ? H6A C6A H6B 108.0 . . ? C11A C7A C6A 115.2(2) . . ? C11A C7A H7A 108.5 . . ? C6A C7A H7A 108.5 . . ? C11A C7A H7B 108.5 . . ? C6A C7A H7B 108.5 . . ? H7A C7A H7B 107.5 . . ? C12A C11A C16A 117.3(2) . . ? C12A C11A C7A 123.8(2) . . ? C16A C11A C7A 118.8(2) . . ? C11A C12A C13A 121.5(2) . . ? C11A C12A H12A 119.2 . . ? C13A C12A H12A 119.2 . . ? C14A C13A C12A 119.7(2) . . ? C14A C13A H13A 120.2 . . ? C12A C13A H13A 120.2 . . ? O14A C14A C13A 116.1(2) . . ? O14A C14A C15A 123.9(2) . . ? C13A C14A C15A 119.9(2) . . ? C14A O14A C141 118.6(2) . . ? O14A C141 H14A 109.5 . . ? O14A C141 H14B 109.5 . . ? H14A C141 H14B 109.5 . . ? O14A C141 H14C 109.5 . . ? H14A C141 H14C 109.5 . . ? H14B C141 H14C 109.5 . . ? C16A C15A C14A 119.2(2) . . ? C16A C15A H15A 120.4 . . ? C14A C15A H15A 120.4 . . ? C15A C16A C11A 122.3(2) . . ? C15A C16A H16A 118.8 . . ? C11A C16A H16A 118.8 . . ? C2B O1B C5B 106.32(19) . . ? N3B C2B O1B 104.2(2) . . ? N3B C2B S2B 131.8(2) . . ? O1B C2B S2B 124.07(19) . . ? C2B N3B N4B 113.3(2) . . ? C2B N3B H3B 127(2) . . ? N4B N3B H3B 120(2) . . ? C5B N4B N3B 103.1(2) . . ? N4B C5B O1B 113.0(2) . . ? N4B C5B C6B 129.2(2) . . ? O1B C5B C6B 117.7(2) . . ? C5B C6B C7B 111.8(2) . . ? C5B C6B H6C 109.3 . . ? C7B C6B H6C 109.3 . . ? C5B C6B H6D 109.3 . . ? C7B C6B H6D 109.3 . . ? H6C C6B H6D 107.9 . . ? C11B C7B C6B 114.6(2) . . ? C11B C7B H7C 108.6 . . ? C6B C7B H7C 108.6 . . ? C11B C7B H7D 108.6 . . ? C6B C7B H7D 108.6 . . ? H7C C7B H7D 107.6 . . ? C12B C11B C16B 117.3(2) . . ? C12B C11B C7B 124.1(2) . . ? C16B C11B C7B 118.5(2) . . ? C13B C12B C11B 121.5(2) . . ? C13B C12B H12B 119.2 . . ? C11B C12B H12B 119.2 . . ? C14B C13B C12B 119.9(2) . . ? C14B C13B H13B 120.1 . . ? C12B C13B H13B 120.1 . . ? O14B C14B C13B 116.2(2) . . ? O14B C14B C15B 124.8(2) . . ? C13B C14B C15B 119.0(2) . . ? C14B O14B C142 118.1(2) . . ? O14B C142 H14D 109.5 . . ? O14B C142 H14E 109.5 . . ? H14D C142 H14E 109.5 . . ? O14B C142 H14F 109.5 . . ? H14D C142 H14F 109.5 . . ? H14E C142 H14F 109.5 . . ? C16B C15B C14B 120.5(2) . . ? C16B C15B H15B 119.8 . . ? C14B C15B H15B 119.8 . . ? C15B C16B C11B 121.8(2) . . ? C15B C16B H16B 119.1 . . ? C11B C16B H16B 119.1 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C141 H14B S2A 0.98 3.00 3.822(3) 142.2 1_365 C142 H14E S2B 0.98 3.00 3.830(3) 143.1 1_365 C16A H16A O1A 0.95 2.53 3.447(3) 163.3 1_455 C16B H16B O1B 0.95 2.57 3.462(3) 156.1 1_455 N3A H3NA O14A 0.85(3) 1.96(3) 2.783(3) 163(3) 1_645 N3B H3B O14B 0.82(3) 1.98(3) 2.774(3) 161(3) 1_645 C142 H14D S2A 0.98 2.89 3.869(3) 172.7 2_656 _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 24.76 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 1.219 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.112 _iucr_refine_instructions_details ; TITL im15 in P-1 CELL 0.71073 7.8075 11.2905 13.2898 88.359 80.741 73.514 ZERR 4.00 0.0008 0.0013 0.0018 0.007 0.006 0.006 LATT 1 SFAC C H N O S UNIT 44 48 8 8 4 TEMP -181 SIZE 0.110 0.280 0.380 L.S.12 BOND $H acta FMAP 2 PLAN 10 mpla s2a c2a o1a c5a n3a n4a C5a c6a c7a c11a c12a c13a c14a o14a c141 c15a c16a mpla s2b c2b o1b c5b n3b n4b C5b c6b c7b c11b c12b c13b c14b o14b c142 c15b c16b mpla 5 c2a o1a c5a n3a n4a s2a c6a mpla 6 c11a c12a c13a c14a c15a c16a o14a c141 mpla c5a c6a c7a c11a mpla 5 c2a o1a c5a n3a n4a s2a c6a mpla 5 c2b o1b c5b n3b n4b s2b c6b mpla 6 c11b c12b c13b c14b c15b c16b o14b c142 mpla c5a c6a c7a c11a mpla 5 c2b o1b c5b n3b n4b s2b c6b EQIV $1 -2+x,1+y,z EQIV $2 -1+x,y,z EQIV $3 1+x,-1+y,z EQIV $4 1-x,-y,1-z HTAB C141 S2a_$1 HTAB C142 S2b_$1 HTAB C16a O1a_$2 HTAB C16b O1b_$2 HTAB N3a O14a_$3 HTAB N3b O14b_$3 HTAB C142 S2a_$4 WGHT 0.114600 FVAR 0.09109 O1A 4 0.913610 -0.216617 0.356674 11.00000 0.01698 0.01097 = 0.01900 0.00005 -0.00175 -0.00408 C2A 1 1.002492 -0.339146 0.367814 11.00000 0.02010 0.01349 = 0.01291 -0.00237 -0.00401 -0.00311 S2A 5 1.224372 -0.394157 0.354741 11.00000 0.01470 0.02175 = 0.02356 -0.00208 -0.00346 -0.00301 N3A 3 0.871118 -0.394427 0.389787 11.00000 0.01536 0.00945 = 0.02703 0.00112 -0.00317 -0.00134 H3NA 2 0.882807 -0.471088 0.393715 11.00000 -1.20000 N4A 3 0.698395 -0.312785 0.391586 11.00000 0.01302 0.01202 = 0.02240 -0.00024 -0.00183 -0.00109 C5A 1 0.731163 -0.208275 0.372307 11.00000 0.01306 0.01792 = 0.01311 -0.00129 -0.00200 -0.00489 C6A 1 0.602209 -0.085896 0.365452 11.00000 0.02005 0.01326 = 0.01890 -0.00022 -0.00296 -0.00525 AFIX 23 H6A 2 0.627675 -0.052495 0.296737 11.00000 -1.20000 H6B 2 0.618252 -0.028826 0.416014 11.00000 -1.20000 AFIX 0 C7A 1 0.406455 -0.092544 0.385211 11.00000 0.01680 0.01373 = 0.01829 -0.00102 -0.00199 -0.00371 AFIX 23 H7A 2 0.392895 -0.150919 0.334910 11.00000 -1.20000 H7B 2 0.383304 -0.126915 0.453775 11.00000 -1.20000 AFIX 0 C11A 1 0.262708 0.030275 0.379405 11.00000 0.01902 0.01234 = 0.01213 0.00185 -0.00148 -0.00409 C12A 1 0.297635 0.144829 0.376772 11.00000 0.01379 0.01527 = 0.01443 0.00004 0.00051 -0.00512 AFIX 43 H12A 2 0.418116 0.148135 0.375832 11.00000 -1.20000 AFIX 0 C13A 1 0.159771 0.254677 0.375487 11.00000 0.01979 0.00871 = 0.01847 -0.00271 -0.00151 -0.00694 AFIX 43 H13A 2 0.186621 0.331768 0.373263 11.00000 -1.20000 AFIX 0 C14A 1 -0.016593 0.250882 0.377469 11.00000 0.01645 0.01251 = 0.00936 0.00036 -0.00089 -0.00236 O14A 4 -0.145223 0.363536 0.376616 11.00000 0.01337 0.01138 = 0.02360 -0.00133 -0.00244 0.00050 C141 1 -0.333903 0.366353 0.390954 11.00000 0.01665 0.02207 = 0.02475 -0.00055 -0.00529 -0.00541 AFIX 137 H14A 2 -0.354965 0.319080 0.335790 11.00000 -1.50000 H14B 2 -0.409009 0.452103 0.390206 11.00000 -1.50000 H14C 2 -0.365611 0.329785 0.456584 11.00000 -1.50000 AFIX 0 C15A 1 -0.054847 0.137056 0.378685 11.00000 0.01195 0.01792 = 0.01267 0.00174 -0.00222 -0.00570 AFIX 43 H15A 2 -0.175063 0.133688 0.378720 11.00000 -1.20000 AFIX 0 C16A 1 0.084081 0.029719 0.379834 11.00000 0.02098 0.01551 = 0.01418 0.00018 -0.00155 -0.00854 AFIX 43 H16A 2 0.057182 -0.047305 0.380957 11.00000 -1.20000 AFIX 0 O1B 4 1.030547 0.021082 0.861686 11.00000 0.01442 0.01331 = 0.02215 0.00025 -0.00418 -0.00431 C2B 1 1.121792 -0.103080 0.863627 11.00000 0.02276 0.01050 = 0.01321 0.00178 -0.00366 -0.00165 S2B 5 1.343529 -0.158176 0.845663 11.00000 0.01522 0.02176 = 0.02319 0.00068 -0.00426 -0.00359 N3B 3 0.989995 -0.159011 0.881994 11.00000 0.01563 0.01395 = 0.02305 0.00291 -0.00009 -0.00111 H3B 2 1.003017 -0.233961 0.884223 11.00000 -1.20000 N4B 3 0.817309 -0.077482 0.889459 11.00000 0.01237 0.01542 = 0.02337 0.00230 -0.00158 -0.00248 C5B 1 0.848030 0.028802 0.877348 11.00000 0.01361 0.01675 = 0.01290 -0.00075 -0.00151 -0.00533 C6B 1 0.719021 0.151689 0.874839 11.00000 0.01666 0.01344 = 0.01808 -0.00294 -0.00073 -0.00393 AFIX 23 H6C 2 0.743338 0.188489 0.807423 11.00000 -1.20000 H6D 2 0.736502 0.205788 0.927300 11.00000 -1.20000 AFIX 0 C7B 1 0.522004 0.145873 0.894348 11.00000 0.01795 0.01583 = 0.02023 0.00215 -0.00421 -0.00606 AFIX 23 H7C 2 0.510020 0.083157 0.847459 11.00000 -1.20000 H7D 2 0.494925 0.117885 0.964868 11.00000 -1.20000 AFIX 0 C11B 1 0.382175 0.267412 0.880459 11.00000 0.01792 0.01502 = 0.01370 -0.00134 -0.00074 -0.00370 C12B 1 0.421564 0.380346 0.864816 11.00000 0.01564 0.01809 = 0.01908 0.00205 0.00169 -0.00612 AFIX 43 H12B 2 0.543370 0.382622 0.859636 11.00000 -1.20000 AFIX 0 C13B 1 0.286521 0.489623 0.856638 11.00000 0.02222 0.01246 = 0.02122 0.00270 0.00114 -0.00616 AFIX 43 H13B 2 0.316443 0.565423 0.846199 11.00000 -1.20000 AFIX 0 C14B 1 0.107724 0.487653 0.863776 11.00000 0.02158 0.01147 = 0.01300 0.00075 -0.00123 -0.00121 O14B 4 -0.017733 0.599766 0.856031 11.00000 0.01696 0.01445 = 0.02528 0.00129 -0.00084 -0.00027 C142 1 -0.204852 0.602707 0.866642 11.00000 0.01479 0.02780 = 0.01999 -0.00029 -0.00406 -0.00103 AFIX 137 H14D 2 -0.220643 0.549190 0.814184 11.00000 -1.50000 H14E 2 -0.278423 0.687561 0.858685 11.00000 -1.50000 H14F 2 -0.243200 0.573376 0.934301 11.00000 -1.50000 AFIX 0 C15B 1 0.067679 0.374545 0.877103 11.00000 0.01457 0.01030 = 0.01357 0.00332 -0.00676 -0.00684 AFIX 43 H15B 2 -0.053288 0.371542 0.879527 11.00000 -1.20000 AFIX 0 C16B 1 0.201609 0.268106 0.886681 11.00000 0.02521 0.01385 = 0.01807 -0.00066 -0.00241 -0.00821 AFIX 43 H16B 2 0.170874 0.192663 0.897864 11.00000 -1.20000 HKLF 4 REM im15 in P-1 REM R1 = 0.0566 for 2673 Fo > 4sig(Fo) and 0.0788 for all 3699 data REM 297 parameters refined using 0 restraints END ; _database_code_depnum_ccdc_archive 'CCDC 964320'