# 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_2 _database_code_depnum_ccdc_archive 'CCDC 899288' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H9 N O5 S Sr' _chemical_formula_sum 'C9 H9 N O5 S Sr' _chemical_formula_weight 330.85 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' Sr Sr -1.5307 3.2498 '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 6.0078(4) _cell_length_b 16.9401(12) _cell_length_c 13.0061(8) _cell_angle_alpha 90.00 _cell_angle_beta 116.158(3) _cell_angle_gamma 90.00 _cell_volume 1188.10(14) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.850 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 4.721 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4519 _exptl_absorpt_correction_T_max 0.7982 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9644 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 25.99 _reflns_number_total 2344 _reflns_number_gt 1926 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0320P)^2^+0.3092P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0038(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2344 _refine_ls_number_parameters 187 _refine_ls_number_restraints 165 _refine_ls_R_factor_all 0.0331 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0592 _refine_ls_wR_factor_gt 0.0569 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.088 _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 Sr1 Sr 0.81786(4) 0.499467(12) 0.594304(18) 0.01903(10) Uani 1 1 d . . . S1 S 0.40700(12) 0.24147(4) 0.29953(6) 0.02631(17) Uani 1 1 d . . . N1 N 0.8297(5) 0.59444(17) 0.9287(2) 0.0468(7) Uani 1 1 d U . . O1 O 0.1786(3) 0.09262(11) 0.18845(17) 0.0362(5) Uani 1 1 d . . . O2 O 0.4481(3) 0.06210(10) 0.11886(15) 0.0276(4) Uani 1 1 d . . . O3 O 0.5156(3) 0.39432(10) 0.42877(16) 0.0293(4) Uani 1 1 d . . . O4 O 0.8810(3) 0.41452(10) 0.43023(16) 0.0282(4) Uani 1 1 d . . . O5 O 0.9407(4) 0.54264(16) 0.79947(19) 0.0605(7) Uani 1 1 d U . . C1 C 0.6818(4) 0.37694(14) 0.3990(2) 0.0222(5) Uani 1 1 d U . . C2 C 0.6470(4) 0.30611(14) 0.3267(2) 0.0225(5) Uani 1 1 d U . . C3 C 0.7909(5) 0.28169(15) 0.2758(2) 0.0298(5) Uani 1 1 d U . . H3 H 0.9293 0.3092 0.2807 0.036 Uiso 1 1 calc R . . C4 C 0.7075(5) 0.21037(15) 0.2149(2) 0.0312(6) Uani 1 1 d U . . H4 H 0.7847 0.1860 0.1752 0.037 Uiso 1 1 calc R . . C5 C 0.5016(4) 0.18086(14) 0.2204(2) 0.0229(5) Uani 1 1 d U . . C6 C 0.3645(4) 0.10591(14) 0.1715(2) 0.0235(5) Uani 1 1 d U . . C7 C 0.7910(8) 0.5489(3) 0.8440(4) 0.0490(11) Uani 0.761(4) 1 d PU A 1 H7 H 0.6464 0.5190 0.8135 0.059 Uiso 0.761(4) 1 calc PR A 1 C8 C 1.0502(10) 0.6469(4) 0.9774(5) 0.0780(15) Uani 0.761(4) 1 d PU A 1 H8A H 1.1315 0.6467 0.9283 0.117 Uiso 0.761(4) 1 calc PR A 1 H8B H 1.1629 0.6283 1.0521 0.117 Uiso 0.761(4) 1 calc PR A 1 H8C H 0.9988 0.6997 0.9833 0.117 Uiso 0.761(4) 1 calc PR A 1 C9 C 0.6564(10) 0.6043(4) 0.9785(5) 0.0714(14) Uani 0.761(4) 1 d PU A 1 H9A H 0.5144 0.5712 0.9389 0.107 Uiso 0.761(4) 1 calc PR A 1 H9B H 0.6044 0.6585 0.9715 0.107 Uiso 0.761(4) 1 calc PR A 1 H9C H 0.7363 0.5899 1.0580 0.107 Uiso 0.761(4) 1 calc PR A 1 C7' C 0.970(3) 0.5940(10) 0.8747(13) 0.058(2) Uani 0.239(4) 1 d PU A 2 H7' H 1.0932 0.6321 0.8922 0.070 Uiso 0.239(4) 1 calc PR A 2 C8' C 0.816(3) 0.6466(11) 1.0073(14) 0.070(3) Uani 0.239(4) 1 d PU A 2 H8'1 H 0.7027 0.6883 0.9677 0.104 Uiso 0.239(4) 1 calc PR A 2 H8'2 H 0.9776 0.6685 1.0530 0.104 Uiso 0.239(4) 1 calc PR A 2 H8'3 H 0.7595 0.6193 1.0560 0.104 Uiso 0.239(4) 1 calc PR A 2 C9' C 0.624(3) 0.5291(11) 0.8825(16) 0.071(3) Uani 0.239(4) 1 d PU A 2 H9'1 H 0.5827 0.5181 0.8037 0.106 Uiso 0.239(4) 1 calc PR A 2 H9'2 H 0.4784 0.5474 0.8883 0.106 Uiso 0.239(4) 1 calc PR A 2 H9'3 H 0.6836 0.4819 0.9270 0.106 Uiso 0.239(4) 1 calc PR A 2 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 Sr1 0.01577(13) 0.01957(14) 0.02276(15) -0.00113(9) 0.00942(10) 0.00054(9) S1 0.0229(3) 0.0234(3) 0.0400(4) -0.0117(3) 0.0205(3) -0.0064(3) N1 0.0466(16) 0.0639(18) 0.0318(14) -0.0056(13) 0.0189(12) 0.0046(14) O1 0.0298(10) 0.0390(11) 0.0475(12) -0.0220(9) 0.0242(9) -0.0159(9) O2 0.0302(10) 0.0231(9) 0.0318(10) -0.0096(8) 0.0156(8) -0.0039(8) O3 0.0308(10) 0.0227(9) 0.0450(12) -0.0075(8) 0.0263(9) -0.0024(8) O4 0.0242(9) 0.0216(9) 0.0405(11) -0.0091(8) 0.0158(9) -0.0070(7) O5 0.0564(15) 0.0899(19) 0.0331(13) -0.0147(13) 0.0179(12) 0.0089(14) C1 0.0238(12) 0.0166(11) 0.0292(13) -0.0009(9) 0.0143(10) -0.0008(9) C2 0.0200(11) 0.0203(11) 0.0303(12) -0.0036(10) 0.0138(10) -0.0028(9) C3 0.0271(11) 0.0264(12) 0.0426(13) -0.0094(10) 0.0215(11) -0.0078(10) C4 0.0332(12) 0.0293(12) 0.0419(13) -0.0114(11) 0.0263(11) -0.0060(10) C5 0.0241(11) 0.0209(11) 0.0271(12) -0.0077(10) 0.0144(10) -0.0026(9) C6 0.0241(12) 0.0218(11) 0.0253(13) -0.0043(10) 0.0115(10) -0.0037(10) C7 0.049(2) 0.065(3) 0.035(2) -0.0071(19) 0.0199(18) 0.003(2) C8 0.076(3) 0.092(3) 0.057(3) -0.021(3) 0.021(2) -0.014(3) C9 0.070(3) 0.094(3) 0.060(3) -0.011(3) 0.038(2) 0.011(3) C7' 0.057(4) 0.073(4) 0.046(4) -0.008(3) 0.024(3) -0.001(4) C8' 0.067(5) 0.082(5) 0.054(4) -0.018(4) 0.022(4) 0.005(4) C9' 0.063(5) 0.080(5) 0.061(5) -0.007(4) 0.020(4) -0.003(4) _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 Sr1 O4 2.4509(17) 3_766 ? Sr1 O1 2.5079(17) 4_666 ? Sr1 O5 2.542(2) . ? Sr1 O2 2.5982(17) 4_566 ? Sr1 O3 2.6095(17) 3_666 ? Sr1 O2 2.7312(17) 2_655 ? Sr1 O4 2.7354(17) . ? Sr1 O3 2.7674(18) . ? Sr1 Sr1 3.5135(5) 3_666 ? Sr1 Sr1 3.9422(5) 3_766 ? S1 C5 1.718(2) . ? S1 C2 1.719(2) . ? N1 C7 1.279(5) . ? N1 C7' 1.315(15) . ? N1 C8' 1.381(16) . ? N1 C9 1.459(5) . ? N1 C8 1.486(6) . ? N1 C9' 1.570(17) . ? O1 C6 1.251(3) . ? O1 Sr1 2.5079(17) 4_465 ? O2 C6 1.255(3) . ? O2 Sr1 2.5982(17) 4_565 ? O2 Sr1 2.7312(17) 2_645 ? O3 C1 1.254(3) . ? O3 Sr1 2.6095(17) 3_666 ? O4 C1 1.255(3) . ? O4 Sr1 2.4509(16) 3_766 ? O5 C7' 1.263(15) . ? O5 C7 1.271(5) . ? C1 C2 1.481(3) . ? C2 C3 1.365(3) . ? C3 C4 1.410(4) . ? C3 H3 0.9300 . ? C4 C5 1.365(3) . ? C4 H4 0.9300 . ? C5 C6 1.495(3) . ? C7 H7 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C7' H7' 0.9300 . ? C8' H8'1 0.9600 . ? C8' H8'2 0.9600 . ? C8' H8'3 0.9600 . ? C9' H9'1 0.9600 . ? C9' H9'2 0.9600 . ? C9' H9'3 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 Sr1 O1 84.54(6) 3_766 4_666 ? O4 Sr1 O5 94.37(7) 3_766 . ? O1 Sr1 O5 82.99(7) 4_666 . ? O4 Sr1 O2 167.13(5) 3_766 4_566 ? O1 Sr1 O2 106.97(5) 4_666 4_566 ? O5 Sr1 O2 81.65(7) . 4_566 ? O4 Sr1 O3 98.53(6) 3_766 3_666 ? O1 Sr1 O3 159.93(6) 4_666 3_666 ? O5 Sr1 O3 77.02(7) . 3_666 ? O2 Sr1 O3 68.67(5) 4_566 3_666 ? O4 Sr1 O2 76.82(6) 3_766 2_655 ? O1 Sr1 O2 136.90(6) 4_666 2_655 ? O5 Sr1 O2 136.30(7) . 2_655 ? O2 Sr1 O2 97.55(5) 4_566 2_655 ? O3 Sr1 O2 62.58(5) 3_666 2_655 ? O4 Sr1 O4 81.20(5) 3_766 . ? O1 Sr1 O4 70.52(6) 4_666 . ? O5 Sr1 O4 153.41(7) . . ? O2 Sr1 O4 107.75(5) 4_566 . ? O3 Sr1 O4 129.53(6) 3_666 . ? O2 Sr1 O4 68.45(5) 2_655 . ? O4 Sr1 O3 123.39(5) 3_766 . ? O1 Sr1 O3 96.26(6) 4_666 . ? O5 Sr1 O3 142.09(7) . . ? O2 Sr1 O3 62.21(5) 4_566 . ? O3 Sr1 O3 98.46(5) 3_666 . ? O2 Sr1 O3 64.58(5) 2_655 . ? O4 Sr1 O3 47.44(5) . . ? O4 Sr1 Sr1 122.93(4) 3_766 3_666 ? O1 Sr1 Sr1 141.58(5) 4_666 3_666 ? O5 Sr1 Sr1 117.04(5) . 3_666 ? O2 Sr1 Sr1 50.41(4) 4_566 3_666 ? O3 Sr1 Sr1 51.18(4) 3_666 3_666 ? O2 Sr1 Sr1 47.15(4) 2_655 3_666 ? O4 Sr1 Sr1 86.56(4) . 3_666 ? O3 Sr1 Sr1 47.28(3) . 3_666 ? O4 Sr1 Sr1 43.29(4) 3_766 3_766 ? O1 Sr1 Sr1 73.11(4) 4_666 3_766 ? O5 Sr1 Sr1 131.90(6) . 3_766 ? O2 Sr1 Sr1 144.85(4) 4_566 3_766 ? O3 Sr1 Sr1 122.27(4) 3_666 3_766 ? O2 Sr1 Sr1 66.63(4) 2_655 3_766 ? O4 Sr1 Sr1 37.91(3) . 3_766 ? O3 Sr1 Sr1 82.69(4) . 3_766 ? Sr1 Sr1 Sr1 107.237(12) 3_666 3_766 ? C5 S1 C2 92.01(11) . . ? C7 N1 C7' 56.8(7) . . ? C7 N1 C8' 167.4(8) . . ? C7' N1 C8' 131.3(12) . . ? C7 N1 C9 123.9(4) . . ? C7' N1 C9 172.0(8) . . ? C8' N1 C9 46.5(8) . . ? C7 N1 C8 121.2(4) . . ? C7' N1 C8 64.5(8) . . ? C8' N1 C8 68.5(9) . . ? C9 N1 C8 114.7(4) . . ? C7 N1 C9' 55.4(7) . . ? C7' N1 C9' 112.1(10) . . ? C8' N1 C9' 116.2(11) . . ? C9 N1 C9' 69.8(7) . . ? C8 N1 C9' 171.9(8) . . ? C6 O1 Sr1 132.25(16) . 4_465 ? C6 O2 Sr1 150.93(16) . 4_565 ? C6 O2 Sr1 125.99(15) . 2_645 ? Sr1 O2 Sr1 82.45(5) 4_565 2_645 ? C1 O3 Sr1 143.26(16) . 3_666 ? C1 O3 Sr1 93.00(14) . . ? Sr1 O3 Sr1 81.54(5) 3_666 . ? C1 O4 Sr1 155.96(17) . 3_766 ? C1 O4 Sr1 94.50(14) . . ? Sr1 O4 Sr1 98.80(5) 3_766 . ? C7' O5 C7 58.3(7) . . ? C7' O5 Sr1 152.7(7) . . ? C7 O5 Sr1 124.5(3) . . ? O3 C1 O4 123.8(2) . . ? O3 C1 C2 118.5(2) . . ? O4 C1 C2 117.6(2) . . ? C3 C2 C1 127.7(2) . . ? C3 C2 S1 111.13(18) . . ? C1 C2 S1 121.17(17) . . ? C2 C3 C4 112.8(2) . . ? C2 C3 H3 123.6 . . ? C4 C3 H3 123.6 . . ? C5 C4 C3 113.0(2) . . ? C5 C4 H4 123.5 . . ? C3 C4 H4 123.5 . . ? C4 C5 C6 129.1(2) . . ? C4 C5 S1 111.06(18) . . ? C6 C5 S1 119.83(18) . . ? O1 C6 O2 126.4(2) . . ? O1 C6 C5 116.4(2) . . ? O2 C6 C5 117.2(2) . . ? O5 C7 N1 123.1(4) . . ? O5 C7 H7 118.4 . . ? N1 C7 H7 118.4 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? O5 C7' N1 120.9(13) . . ? O5 C7' H7' 119.6 . . ? N1 C7' H7' 119.6 . . ? N1 C8' H8'1 109.5 . . ? N1 C8' H8'2 109.5 . . ? H8'1 C8' H8'2 109.5 . . ? N1 C8' H8'3 109.5 . . ? H8'1 C8' H8'3 109.5 . . ? H8'2 C8' H8'3 109.5 . . ? N1 C9' H9'1 109.5 . . ? N1 C9' H9'2 109.5 . . ? H9'1 C9' H9'2 109.5 . . ? N1 C9' H9'3 109.5 . . ? H9'1 C9' H9'3 109.5 . . ? H9'2 C9' H9'3 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.370 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.066