# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Srinivasulu Aitipamula' _publ_contact_author_email 'SRINIVASULU AITIPAMULA@ICES.A-STAR.EDU.SG' _publ_section_title ; Dimorphs of 1:1 cocrystal of ethenzamide and saccharin: solid-state grinding methods result in metastable polymorph ; loop_ _publ_author_name 'Srinivasulu Aitipamula' 'Pui Shan Chow' 'Reginald B H Tan' # Attachment 'B821373A_Cif.cif' data_EASACFI _database_code_depnum_ccdc_archive 'CCDC 711674' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Form I of 1:1 cocrystal of ethenzamide and saccharin' ; _chemical_name_common "'Form I of 1:1 cocrystal of ethenzamide and saccharin'" _chemical_melting_point 395.57 _chemical_formula_moiety ' C9 H11 N O2, C7 H5 N O3 S' _chemical_formula_sum 'C16 H16 N2 O5 S' _chemical_formula_weight 348.37 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.0000 '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 7.2141(14) _cell_length_b 7.4923(15) _cell_length_c 15.456(3) _cell_angle_alpha 85.14(3) _cell_angle_beta 86.43(3) _cell_angle_gamma 70.65(3) _cell_volume 784.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2460 _cell_measurement_theta_min 2.6468 _cell_measurement_theta_max 30.9526 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9176 _exptl_absorpt_correction_T_max 0.9542 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Rigaku Saturn CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10878 _diffrn_reflns_av_R_equivalents 0.0150 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.65 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3823 _reflns_number_gt 3707 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0457P)^2^+0.4596P] 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 3823 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0392 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0946 _refine_ls_wR_factor_gt 0.0935 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 S1 S 0.14065(5) 0.21941(4) 0.34324(2) 0.01944(9) Uani 1 1 d . . . O3 O 0.20291(15) 0.67494(14) 0.39190(7) 0.0258(2) Uani 1 1 d . . . O5 O -0.05627(15) 0.21497(14) 0.34012(7) 0.0259(2) Uani 1 1 d . . . O4 O 0.28746(16) 0.09552(14) 0.28911(6) 0.0267(2) Uani 1 1 d . . . N2 N 0.14295(18) 0.43899(16) 0.32513(8) 0.0225(2) Uani 1 1 d . . . C16 C 0.21408(18) 0.20163(18) 0.45059(8) 0.0181(2) Uani 1 1 d . . . C15 C 0.24222(18) 0.36914(18) 0.46880(8) 0.0187(2) Uani 1 1 d . . . C12 C 0.30785(19) 0.0656(2) 0.59124(9) 0.0227(3) Uani 1 1 d . . . H12 H 0.3299 -0.0347 0.6333 0.027 Uiso 1 1 calc R . . C11 C 0.3402(2) 0.2311(2) 0.61041(9) 0.0238(3) Uani 1 1 d . . . H11 H 0.3850 0.2384 0.6647 0.029 Uiso 1 1 calc R . . C14 C 0.19659(19) 0.51446(18) 0.39406(8) 0.0204(2) Uani 1 1 d . . . C13 C 0.24328(19) 0.04718(18) 0.51049(8) 0.0205(2) Uani 1 1 d . . . H13 H 0.2210 -0.0627 0.4974 0.025 Uiso 1 1 calc R . . C10 C 0.30669(19) 0.38602(19) 0.54972(9) 0.0219(3) Uani 1 1 d . . . H10 H 0.3268 0.4969 0.5629 0.026 Uiso 1 1 calc R . . O1 O 1.05749(17) -0.38247(14) 0.17163(6) 0.0290(2) Uani 1 1 d . . . O2 O 0.71642(14) 0.18529(13) 0.13330(6) 0.0225(2) Uani 1 1 d . . . N1 N 0.96896(18) -0.09755(17) 0.22766(7) 0.0223(2) Uani 1 1 d . . . C7 C 0.96863(19) -0.20750(18) 0.16474(8) 0.0193(2) Uani 1 1 d . . . C6 C 0.8966(2) -0.24455(18) 0.01591(8) 0.0216(3) Uani 1 1 d . . . H6 H 0.9739 -0.3707 0.0260 0.026 Uiso 1 1 calc R . . C1 C 0.86507(18) -0.12237(17) 0.08292(8) 0.0181(2) Uani 1 1 d . . . C5 C 0.8169(2) -0.1843(2) -0.06499(9) 0.0228(3) Uani 1 1 d . . . H5 H 0.8406 -0.2682 -0.1086 0.027 Uiso 1 1 calc R . . C4 C 0.7008(2) 0.0041(2) -0.07960(8) 0.0224(3) Uani 1 1 d . . . H4 H 0.6459 0.0466 -0.1335 0.027 Uiso 1 1 calc R . . C3 C 0.66597(19) 0.12918(19) -0.01468(9) 0.0217(3) Uani 1 1 d . . . H3 H 0.5880 0.2549 -0.0254 0.026 Uiso 1 1 calc R . . C2 C 0.74715(18) 0.06793(18) 0.06685(8) 0.0184(2) Uani 1 1 d . . . C8 C 0.5996(2) 0.38156(19) 0.11780(9) 0.0249(3) Uani 1 1 d . . . H8A H 0.4678 0.3922 0.1025 0.030 Uiso 1 1 calc R . . H8B H 0.6582 0.4407 0.0705 0.030 Uiso 1 1 calc R . . C9 C 0.5932(2) 0.4766(2) 0.20073(11) 0.0324(3) Uani 1 1 d . . . H9A H 0.5444 0.4106 0.2479 0.049 Uiso 1 1 calc R . . H9B H 0.5080 0.6057 0.1944 0.049 Uiso 1 1 calc R . . H9C H 0.7232 0.4738 0.2127 0.049 Uiso 1 1 calc R . . H1B H 0.912(3) 0.022(3) 0.2202(13) 0.034(5) Uiso 1 1 d . . . H2 H 0.118(3) 0.502(3) 0.2701(16) 0.053(6) Uiso 1 1 d . . . H1A H 1.039(3) -0.153(3) 0.2759(14) 0.039(5) Uiso 1 1 d . . . 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 0.02446(17) 0.01656(15) 0.01745(15) -0.00129(11) -0.00511(11) -0.00612(12) O3 0.0324(5) 0.0195(5) 0.0282(5) -0.0007(4) -0.0044(4) -0.0119(4) O5 0.0269(5) 0.0240(5) 0.0291(5) -0.0013(4) -0.0095(4) -0.0099(4) O4 0.0331(5) 0.0243(5) 0.0192(4) -0.0055(4) -0.0024(4) -0.0036(4) N2 0.0317(6) 0.0185(5) 0.0187(5) 0.0013(4) -0.0066(4) -0.0098(4) C16 0.0183(5) 0.0195(6) 0.0162(5) -0.0027(4) -0.0017(4) -0.0053(4) C15 0.0178(5) 0.0191(6) 0.0187(6) -0.0018(4) -0.0009(4) -0.0053(4) C12 0.0219(6) 0.0250(6) 0.0183(6) 0.0012(5) 0.0001(5) -0.0045(5) C11 0.0229(6) 0.0297(7) 0.0173(6) -0.0038(5) -0.0027(5) -0.0058(5) C14 0.0212(6) 0.0197(6) 0.0205(6) -0.0023(5) -0.0025(5) -0.0063(5) C13 0.0203(6) 0.0199(6) 0.0208(6) -0.0012(5) 0.0005(5) -0.0059(5) C10 0.0218(6) 0.0234(6) 0.0209(6) -0.0056(5) -0.0024(5) -0.0067(5) O1 0.0458(6) 0.0163(4) 0.0214(5) -0.0006(4) -0.0092(4) -0.0041(4) O2 0.0289(5) 0.0158(4) 0.0195(4) -0.0030(3) -0.0025(4) -0.0022(4) N1 0.0316(6) 0.0179(5) 0.0169(5) -0.0009(4) -0.0036(4) -0.0071(5) C7 0.0244(6) 0.0176(6) 0.0166(6) -0.0004(4) -0.0004(5) -0.0081(5) C6 0.0264(6) 0.0178(6) 0.0208(6) -0.0031(5) -0.0011(5) -0.0071(5) C1 0.0219(6) 0.0166(5) 0.0171(6) -0.0006(4) -0.0010(4) -0.0083(5) C5 0.0278(6) 0.0244(6) 0.0187(6) -0.0049(5) -0.0016(5) -0.0108(5) C4 0.0241(6) 0.0273(7) 0.0175(6) 0.0005(5) -0.0031(5) -0.0106(5) C3 0.0228(6) 0.0199(6) 0.0211(6) 0.0015(5) -0.0026(5) -0.0056(5) C2 0.0204(6) 0.0178(6) 0.0178(6) -0.0021(4) 0.0008(4) -0.0072(5) C8 0.0266(6) 0.0169(6) 0.0277(7) -0.0030(5) -0.0049(5) -0.0013(5) C9 0.0358(8) 0.0210(6) 0.0341(8) -0.0091(6) -0.0091(6) 0.0020(6) _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 S1 O4 1.4328(12) . ? S1 O5 1.4358(11) . ? S1 N2 1.6507(12) . ? S1 C16 1.7540(13) . ? O3 C14 1.2158(17) . ? N2 C14 1.3794(17) . ? N2 H2 0.93(2) . ? C16 C13 1.3863(18) . ? C16 C15 1.3897(18) . ? C15 C10 1.3909(18) . ? C15 C14 1.4917(19) . ? C12 C13 1.3922(19) . ? C12 C11 1.394(2) . ? C12 H12 0.9300 . ? C11 C10 1.394(2) . ? C11 H11 0.9300 . ? C13 H13 0.9300 . ? C10 H10 0.9300 . ? O1 C7 1.2525(16) . ? O2 C2 1.3684(15) . ? O2 C8 1.4402(16) . ? N1 C7 1.3272(17) . ? N1 H1B 0.85(2) . ? N1 H1A 0.92(2) . ? C7 C1 1.4932(18) . ? C6 C5 1.3855(19) . ? C6 C1 1.3985(17) . ? C6 H6 0.9300 . ? C1 C2 1.4074(18) . ? C5 C4 1.389(2) . ? C5 H5 0.9300 . ? C4 C3 1.3856(19) . ? C4 H4 0.9300 . ? C3 C2 1.3991(18) . ? C3 H3 0.9300 . ? C8 C9 1.509(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? 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 O4 S1 O5 116.91(7) . . ? O4 S1 N2 110.20(7) . . ? O5 S1 N2 110.26(7) . . ? O4 S1 C16 112.27(7) . . ? O5 S1 C16 111.52(7) . . ? N2 S1 C16 93.17(7) . . ? C14 N2 S1 115.55(10) . . ? C14 N2 H2 123.8(14) . . ? S1 N2 H2 120.5(14) . . ? C13 C16 C15 123.13(12) . . ? C13 C16 S1 127.16(10) . . ? C15 C16 S1 109.71(10) . . ? C16 C15 C10 120.02(12) . . ? C16 C15 C14 112.50(11) . . ? C10 C15 C14 127.48(12) . . ? C13 C12 C11 121.47(13) . . ? C13 C12 H12 119.3 . . ? C11 C12 H12 119.3 . . ? C12 C11 C10 121.25(12) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? O3 C14 N2 123.84(13) . . ? O3 C14 C15 127.12(12) . . ? N2 C14 C15 109.04(11) . . ? C16 C13 C12 116.35(12) . . ? C16 C13 H13 121.8 . . ? C12 C13 H13 121.8 . . ? C15 C10 C11 117.76(13) . . ? C15 C10 H10 121.1 . . ? C11 C10 H10 121.1 . . ? C2 O2 C8 118.48(11) . . ? C7 N1 H1B 119.3(13) . . ? C7 N1 H1A 118.0(13) . . ? H1B N1 H1A 122.5(18) . . ? O1 C7 N1 121.26(12) . . ? O1 C7 C1 118.73(12) . . ? N1 C7 C1 119.99(12) . . ? C5 C6 C1 122.32(12) . . ? C5 C6 H6 118.8 . . ? C1 C6 H6 118.8 . . ? C6 C1 C2 118.21(12) . . ? C6 C1 C7 115.62(11) . . ? C2 C1 C7 126.12(12) . . ? C6 C5 C4 118.62(12) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C3 C4 C5 120.68(12) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C3 C2 120.53(12) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? O2 C2 C3 122.88(12) . . ? O2 C2 C1 117.49(11) . . ? C3 C2 C1 119.63(12) . . ? O2 C8 C9 107.01(12) . . ? O2 C8 H8A 110.3 . . ? C9 C8 H8A 110.3 . . ? O2 C8 H8B 110.3 . . ? C9 C8 H8B 110.3 . . ? H8A C8 H8B 108.6 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.355 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.054 #===END data_EASACFII _database_code_depnum_ccdc_archive 'CCDC 711675' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'Form II of 1:1 cocrystal of ethenzamide and saccharin' ; _chemical_name_common "'Form II of 1:1 cocrystal of ethenzamide and saccharin'" _chemical_melting_point 394.34 _chemical_formula_moiety ' C9 H11 N O2, C7 H5 N O3 S' _chemical_formula_sum 'C16 H16 N2 O5 S' _chemical_formula_weight 348.37 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.6125(17) _cell_length_b 16.607(3) _cell_length_c 11.183(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.45(3) _cell_angle_gamma 90.00 _cell_volume 1598.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5455 _cell_measurement_theta_min 2.1960 _cell_measurement_theta_max 31.0825 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9507 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area deterctor' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12033 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.28 _reflns_number_total 3951 _reflns_number_gt 3526 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0840P)^2^+0.6428P] 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 3951 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0666 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1662 _refine_ls_wR_factor_gt 0.1556 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 S1 S 0.79388(5) 0.13461(3) 0.61302(4) 0.02297(17) Uani 1 1 d . . . O5 O 0.89417(18) 0.13275(9) 0.71728(13) 0.0301(3) Uani 1 1 d . . . O2 O 0.68908(16) 0.25224(8) 0.29227(13) 0.0259(3) Uani 1 1 d . . . O1 O 0.42636(18) 0.04262(9) 0.24510(13) 0.0328(4) Uani 1 1 d . . . O3 O 0.70884(17) -0.05839(9) 0.45456(13) 0.0304(3) Uani 1 1 d . . . C1 C 0.6079(2) 0.13832(11) 0.17672(18) 0.0220(4) Uani 1 1 d . . . O4 O 0.67747(17) 0.19660(9) 0.60821(14) 0.0291(3) Uani 1 1 d . . . N1 N 0.4925(2) 0.14135(11) 0.37444(16) 0.0262(4) Uani 1 1 d . . . C2 C 0.8983(2) 0.13074(12) 0.48024(18) 0.0230(4) Uani 1 1 d . . . N2 N 0.71371(19) 0.04548(10) 0.58961(15) 0.0246(4) Uani 1 1 d . . . C3 C 0.8654(2) 0.05953(12) 0.42008(17) 0.0236(4) Uani 1 1 d . . . C4 C 0.7003(2) 0.20822(12) 0.18952(17) 0.0230(4) Uani 1 1 d . . . C5 C 0.9995(2) 0.18761(13) 0.43699(19) 0.0265(4) Uani 1 1 d . . . H5 H 1.0193 0.2354 0.4781 0.032 Uiso 1 1 calc R . . C6 C 0.8000(2) 0.22955(13) 0.09824(18) 0.0263(4) Uani 1 1 d . . . H6 H 0.8619 0.2752 0.1065 0.032 Uiso 1 1 calc R . . C7 C 0.5021(2) 0.10528(12) 0.26893(18) 0.0246(4) Uani 1 1 d . . . C8 C 0.7552(2) 0.00753(12) 0.48538(17) 0.0241(4) Uani 1 1 d . . . C9 C 0.7675(2) 0.32911(12) 0.2988(2) 0.0286(4) Uani 1 1 d . . . H9A H 0.7366 0.3625 0.2311 0.034 Uiso 1 1 calc R . . H9B H 0.8791 0.3215 0.2977 0.034 Uiso 1 1 calc R . . C10 C 0.7156(3) 0.11475(13) -0.0193(2) 0.0314(5) Uani 1 1 d . . . H10 H 0.7194 0.0840 -0.0886 0.038 Uiso 1 1 calc R . . C11 C 0.9354(2) 0.04323(13) 0.31190(18) 0.0267(4) Uani 1 1 d . . . H11 H 0.9133 -0.0040 0.2701 0.032 Uiso 1 1 calc R . . C12 C 0.8074(2) 0.18309(13) -0.00509(19) 0.0298(5) Uani 1 1 d . . . H12 H 0.8744 0.1979 -0.0652 0.036 Uiso 1 1 calc R . . C13 C 0.6188(2) 0.09366(13) 0.07197(19) 0.0273(4) Uani 1 1 d . . . H13 H 0.5581 0.0476 0.0631 0.033 Uiso 1 1 calc R . . C14 C 1.0708(2) 0.17064(14) 0.32932(19) 0.0297(5) Uani 1 1 d . . . H14 H 1.1404 0.2074 0.2981 0.036 Uiso 1 1 calc R . . C15 C 1.0390(2) 0.09936(14) 0.26798(19) 0.0298(4) Uani 1 1 d . . . H15 H 1.0880 0.0891 0.1964 0.036 Uiso 1 1 calc R . . C16 C 0.7221(3) 0.36851(13) 0.4137(2) 0.0345(5) Uani 1 1 d . . . H16A H 0.6130 0.3804 0.4105 0.052 Uiso 1 1 calc R . . H16B H 0.7798 0.4175 0.4247 0.052 Uiso 1 1 calc R . . H16C H 0.7446 0.3328 0.4794 0.052 Uiso 1 1 calc R . . H1 H 0.553(3) 0.1826(15) 0.386(2) 0.026(6) Uiso 1 1 d . . . H2 H 0.433(3) 0.1216(16) 0.432(3) 0.042(8) Uiso 1 1 d . . . H3 H 0.662(4) 0.018(2) 0.645(3) 0.068(10) Uiso 1 1 d . . . 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 0.0243(3) 0.0230(3) 0.0217(3) -0.00106(17) 0.00288(19) -0.00114(17) O5 0.0328(8) 0.0337(8) 0.0237(7) -0.0016(6) -0.0008(6) -0.0029(6) O2 0.0294(7) 0.0230(7) 0.0253(7) 0.0015(5) 0.0010(5) -0.0047(6) O1 0.0406(8) 0.0311(8) 0.0270(8) -0.0036(6) 0.0072(6) -0.0143(6) O3 0.0381(8) 0.0259(8) 0.0275(8) -0.0023(6) 0.0071(6) -0.0050(6) C1 0.0192(8) 0.0215(9) 0.0255(10) 0.0036(7) 0.0014(7) 0.0007(7) O4 0.0294(7) 0.0264(8) 0.0317(8) -0.0028(6) 0.0047(6) 0.0041(6) N1 0.0271(8) 0.0255(9) 0.0261(9) -0.0008(7) 0.0058(7) -0.0052(7) C2 0.0195(8) 0.0254(10) 0.0242(9) 0.0031(7) 0.0019(7) 0.0009(7) N2 0.0272(8) 0.0241(8) 0.0227(8) -0.0008(6) 0.0050(6) -0.0025(6) C3 0.0222(8) 0.0268(10) 0.0217(9) 0.0027(7) 0.0012(7) 0.0031(7) C4 0.0221(8) 0.0227(9) 0.0241(9) 0.0026(7) -0.0018(7) 0.0016(7) C5 0.0249(9) 0.0261(10) 0.0286(10) 0.0016(8) 0.0006(7) -0.0007(7) C6 0.0227(9) 0.0256(10) 0.0308(10) 0.0072(8) 0.0022(7) -0.0011(7) C7 0.0238(9) 0.0256(10) 0.0246(9) 0.0042(8) 0.0018(7) -0.0013(7) C8 0.0256(9) 0.0234(9) 0.0233(9) 0.0008(7) 0.0019(7) 0.0008(7) C9 0.0291(10) 0.0221(10) 0.0344(11) 0.0028(8) -0.0017(8) -0.0057(8) C10 0.0350(11) 0.0303(11) 0.0291(11) 0.0006(9) 0.0080(8) 0.0021(9) C11 0.0289(9) 0.0277(10) 0.0237(9) 0.0013(8) 0.0028(7) 0.0033(8) C12 0.0282(10) 0.0320(11) 0.0295(10) 0.0041(8) 0.0077(8) 0.0037(8) C13 0.0267(9) 0.0271(10) 0.0282(10) 0.0013(8) 0.0035(7) -0.0009(8) C14 0.0230(9) 0.0351(11) 0.0311(11) 0.0075(9) 0.0040(8) -0.0008(8) C15 0.0275(9) 0.0374(12) 0.0247(10) 0.0050(9) 0.0047(7) 0.0050(8) C16 0.0403(12) 0.0266(11) 0.0367(12) -0.0018(9) -0.0001(9) -0.0070(9) _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 S1 O5 1.4337(16) . ? S1 O4 1.4370(15) . ? S1 N2 1.6512(18) . ? S1 C2 1.757(2) . ? O2 C4 1.367(2) . ? O2 C9 1.445(2) . ? O1 C7 1.253(2) . ? O3 C8 1.212(2) . ? C1 C13 1.392(3) . ? C1 C4 1.412(3) . ? C1 C7 1.498(3) . ? N1 C7 1.328(3) . ? N1 H1 0.87(3) . ? N1 H2 0.90(3) . ? C2 C5 1.381(3) . ? C2 C3 1.386(3) . ? N2 C8 1.380(3) . ? N2 H3 0.90(3) . ? C3 C11 1.392(3) . ? C3 C8 1.488(3) . ? C4 C6 1.396(3) . ? C5 C14 1.394(3) . ? C5 H5 0.9300 . ? C6 C12 1.392(3) . ? C6 H6 0.9300 . ? C9 C16 1.503(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C13 1.380(3) . ? C10 C12 1.390(3) . ? C10 H10 0.9300 . ? C11 C15 1.389(3) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.392(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? 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 O5 S1 O4 116.81(9) . . ? O5 S1 N2 110.52(9) . . ? O4 S1 N2 110.34(9) . . ? O5 S1 C2 112.07(9) . . ? O4 S1 C2 111.49(9) . . ? N2 S1 C2 93.11(9) . . ? C4 O2 C9 118.13(16) . . ? C13 C1 C4 118.28(18) . . ? C13 C1 C7 116.05(17) . . ? C4 C1 C7 125.62(18) . . ? C7 N1 H1 116.0(17) . . ? C7 N1 H2 121.7(18) . . ? H1 N1 H2 122(2) . . ? C5 C2 C3 122.46(19) . . ? C5 C2 S1 127.76(16) . . ? C3 C2 S1 109.78(14) . . ? C8 N2 S1 115.28(14) . . ? C8 N2 H3 120(2) . . ? S1 N2 H3 124(2) . . ? C2 C3 C11 119.99(18) . . ? C2 C3 C8 112.46(17) . . ? C11 C3 C8 127.54(19) . . ? O2 C4 C6 122.45(18) . . ? O2 C4 C1 118.23(17) . . ? C6 C4 C1 119.32(19) . . ? C2 C5 C14 117.4(2) . . ? C2 C5 H5 121.3 . . ? C14 C5 H5 121.3 . . ? C12 C6 C4 120.55(19) . . ? C12 C6 H6 119.7 . . ? C4 C6 H6 119.7 . . ? O1 C7 N1 121.33(18) . . ? O1 C7 C1 118.71(18) . . ? N1 C7 C1 119.95(18) . . ? O3 C8 N2 124.21(18) . . ? O3 C8 C3 126.43(18) . . ? N2 C8 C3 109.36(17) . . ? O2 C9 C16 107.22(17) . . ? O2 C9 H9A 110.3 . . ? C16 C9 H9A 110.3 . . ? O2 C9 H9B 110.3 . . ? C16 C9 H9B 110.3 . . ? H9A C9 H9B 108.5 . . ? C13 C10 C12 118.4(2) . . ? C13 C10 H10 120.8 . . ? C12 C10 H10 120.8 . . ? C15 C11 C3 118.2(2) . . ? C15 C11 H11 120.9 . . ? C3 C11 H11 120.9 . . ? C10 C12 C6 120.62(19) . . ? C10 C12 H12 119.7 . . ? C6 C12 H12 119.7 . . ? C10 C13 C1 122.8(2) . . ? C10 C13 H13 118.6 . . ? C1 C13 H13 118.6 . . ? C15 C14 C5 120.82(19) . . ? C15 C14 H14 119.6 . . ? C5 C14 H14 119.6 . . ? C11 C15 C14 121.1(2) . . ? C11 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C9 C16 H16A 109.5 . . ? C9 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C9 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.603 _refine_diff_density_min -0.562 _refine_diff_density_rms 0.076 #===END