# 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_1 _audit_creation_date 2013-04-20T23:22:55-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_formula_moiety 'C22 H30 N6 O4 S, C9 H8 O4' _chemical_formula_sum 'C31 H38 N6 O8 S' _chemical_formula_weight 654.73 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _cell_length_a 9.6707(7) _cell_length_b 12.3070(7) _cell_length_c 14.5432(12) _cell_angle_alpha 85.266(2) _cell_angle_beta 74.549(5) _cell_angle_gamma 82.829(6) _cell_volume 1653.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_reflns_used 2121 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 692 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.361 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details ; North, A. C. T., Phillips, D. C. & Mathews, F. S. Acta Cryst, 1968, A24, 351-359. ; _exptl_absorpt_correction_T_min 0.7271 _exptl_absorpt_correction_T_max 0.9351 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_monochromator 'graded mirror' _diffrn_reflns_av_R_equivalents 0.293 _diffrn_reflns_av_unetI/netI 0.0949 _diffrn_reflns_number 5897 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 64.84 _diffrn_reflns_theta_full 64.84 _diffrn_measurement_method CCD _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.875 _diffrn_measured_fraction_theta_max 0.875 _reflns_number_total 4910 _reflns_number_gt 2247 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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. The checkCIF report entails three level-A alerts referring to: 1) Rint > 0.25 2) , three level-B alerts and numerous ; _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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_coef 0.021(3) _refine_ls_number_reflns 4910 _refine_ls_number_parameters 424 _refine_ls_number_restraints 17 _refine_ls_R_factor_all 0.187 _refine_ls_R_factor_gt 0.1244 _refine_ls_wR_factor_ref 0.3654 _refine_ls_wR_factor_gt 0.3147 _refine_ls_goodness_of_fit_ref 1.12 _refine_ls_restrained_S_all 1.121 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.469 _refine_diff_density_min -0.713 _refine_diff_density_rms 0.1 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 0.7154(3) 0.04038(15) 0.14337(12) 0.1027(8) Uani 1 1 d . . . O7 O 0.2934(6) 0.5519(4) 0.2345(4) 0.1027(15) Uani 1 1 d U . . O5 O -0.0243(8) 0.4235(5) 0.1451(5) 0.132(2) Uani 1 1 d . . . H5 H -0.0058 0.3633 0.1218 0.198 Uiso 1 1 calc R . . N1 N 1.0645(7) 0.2610(5) 0.0326(4) 0.1020(19) Uani 1 1 d . . . O4 O 0.4758(6) 0.2580(4) 0.7233(4) 0.1107(16) Uani 1 1 d . . . N2 N 0.8519(7) 0.1114(4) 0.0928(3) 0.0934(17) Uani 1 1 d U . . O1 O 0.7779(7) -0.0605(4) 0.1813(3) 0.1184(19) Uani 1 1 d . . . O6 O 0.1810(8) 0.3788(4) 0.1857(5) 0.132(2) Uani 1 1 d . . . C4 C 0.8174(8) 0.2200(5) 0.0460(5) 0.090(2) Uani 1 1 d . . . H4A H 0.7786 0.2741 0.0937 0.107 Uiso 1 1 calc R . . H4B H 0.746 0.2149 0.0111 0.107 Uiso 1 1 calc R . . C25 C -0.0965(9) 0.6037(7) 0.2527(5) 0.103(2) Uani 1 1 d . . . H25 H -0.1715 0.5728 0.2393 0.124 Uiso 1 1 calc R . . N6 N 0.6773(6) 0.0506(4) 0.5061(4) 0.0843(15) Uani 1 1 d . . . O3 O 0.3618(7) 0.3047(5) 0.4610(4) 0.1225(19) Uani 1 1 d U . . N4 N 0.6977(7) 0.0591(5) 0.7442(4) 0.0906(16) Uani 1 1 d . . . N3 N 0.5102(7) 0.1988(5) 0.5737(4) 0.0885(16) Uani 1 1 d D . . C26 C -0.1248(11) 0.7053(8) 0.2938(6) 0.117(3) Uani 1 1 d . . . H26 H -0.2185 0.7401 0.3091 0.14 Uiso 1 1 calc R . . C13 C 0.5356(8) 0.1913(5) 0.6635(5) 0.0841(18) Uani 1 1 d . . . C17 C 0.2741(14) 0.4114(7) 0.4478(6) 0.193(5) Uani 1 1 d DU . . H17A H 0.1906 0.4237 0.5017 0.232 Uiso 1 1 calc R . . H17B H 0.2426 0.4145 0.3896 0.232 Uiso 1 1 calc RD . . C23 C 0.0728(10) 0.4387(7) 0.1844(6) 0.105(2) Uani 1 1 d . . . O8 O 0.3382(7) 0.6174(6) 0.0843(4) 0.145(2) Uani 1 1 d . . . O2 O 0.6400(8) 0.0387(5) 0.0727(4) 0.128(2) Uani 1 1 d . . . C24 C 0.0425(8) 0.5474(6) 0.2313(5) 0.0861(19) Uani 1 1 d . . . C8 C 0.4191(9) 0.2565(6) 0.2952(5) 0.108(2) Uani 1 1 d . . . H8 H 0.3476 0.31 0.2843 0.13 Uiso 1 1 calc RD . . C12 C 0.5818(7) 0.1315(6) 0.4983(4) 0.0829(18) Uani 1 1 d . . . C14 C 0.6406(8) 0.0982(5) 0.6718(5) 0.0835(18) Uani 1 1 d . . . C29 C 0.1501(8) 0.6012(6) 0.2520(5) 0.0908(19) Uani 1 1 d U . . C1 C 1.2038(10) 0.2938(7) -0.0333(6) 0.126(3) Uani 1 1 d . . . H1A H 1.2401 0.2415 -0.0818 0.189 Uiso 1 1 calc R . . H1B H 1.2734 0.2956 0.0028 0.189 Uiso 1 1 calc R . . H1C H 1.1865 0.3652 -0.0627 0.189 Uiso 1 1 calc R . . C7 C 0.4976(9) 0.1956(7) 0.2236(5) 0.103(2) Uani 1 1 d . . . H7 H 0.4808 0.2073 0.1633 0.123 Uiso 1 1 calc R . . N5 N 0.8010(7) -0.0271(5) 0.7164(4) 0.0945(17) Uani 1 1 d . . . C5 C 0.9554(9) 0.2532(6) -0.0217(5) 0.104(2) Uani 1 1 d . . . H5A H 0.9927 0.1994 -0.0698 0.125 Uiso 1 1 calc R . . H5B H 0.936 0.3235 -0.0538 0.125 Uiso 1 1 calc R . . C30 C 0.3809(10) 0.5636(7) 0.1460(6) 0.110(2) Uani 1 1 d . . . C28 C 0.1211(12) 0.7020(7) 0.2940(5) 0.112(2) Uani 1 1 d U . . H28 H 0.193 0.7342 0.31 0.134 Uiso 1 1 calc R . . C16 C 0.7063(7) 0.0356(5) 0.5943(4) 0.0788(17) Uani 1 1 d . . . C6 C 0.6062(9) 0.1131(5) 0.2393(5) 0.092(2) Uani 1 1 d . . . C18 C 0.3830(19) 0.4945(16) 0.4418(15) 0.291(9) Uani 1 1 d DU . . H18A H 0.3382 0.5674 0.4331 0.436 Uiso 0.5 1 calc PR . . H18B H 0.4652 0.4794 0.3887 0.436 Uiso 0.5 1 calc PR . . H18C H 0.4136 0.4886 0.4998 0.436 Uiso 0.5 1 calc PR . . H18D H 0.4731 0.4562 0.4479 0.436 Uiso 0.5 1 calc PR . . H18E H 0.3462 0.5442 0.4923 0.436 Uiso 0.5 1 calc PR . . H18F H 0.3977 0.535 0.3813 0.436 Uiso 0.5 1 calc PR . . C10 C 0.5482(8) 0.1583(5) 0.4040(4) 0.0809(17) Uani 1 1 d . . . C27 C -0.0194(13) 0.7527(7) 0.3111(6) 0.123(3) Uani 1 1 d . . . H27 H -0.04 0.8221 0.3355 0.147 Uiso 1 1 calc R . . C9 C 0.4428(9) 0.2412(6) 0.3852(5) 0.097(2) Uani 1 1 d . . . C31 C 0.5274(9) 0.5122(7) 0.1397(7) 0.135(3) Uani 1 1 d . . . H31A H 0.5804 0.5093 0.0738 0.202 Uiso 1 1 calc R . . H31B H 0.5237 0.4392 0.1684 0.202 Uiso 1 1 calc R . . H31C H 0.5743 0.5544 0.1727 0.202 Uiso 1 1 calc R . . C2 C 1.0944(9) 0.1569(6) 0.0861(5) 0.101(2) Uani 1 1 d U . . H2A H 1.1592 0.1671 0.1246 0.121 Uiso 1 1 calc R . . H2B H 1.141 0.1007 0.0415 0.121 Uiso 1 1 calc R . . C15 C 0.8070(8) -0.0409(5) 0.6255(5) 0.0869(19) Uani 1 1 d . . . C20 C 0.9097(9) -0.1299(5) 0.5715(5) 0.096(2) Uani 1 1 d . . . H20A H 0.8531 -0.1803 0.5534 0.115 Uiso 1 1 calc R . . H20B H 0.9661 -0.0966 0.513 0.115 Uiso 1 1 calc R . . C19 C 0.6618(9) 0.0925(6) 0.8412(5) 0.105(2) Uani 1 1 d . . . H19A H 0.6144 0.1659 0.8443 0.158 Uiso 1 1 calc R . . H19B H 0.7484 0.0899 0.8621 0.158 Uiso 1 1 calc R . . H19C H 0.5987 0.0438 0.8819 0.158 Uiso 1 1 calc R . . C11 C 0.6249(8) 0.0970(6) 0.3296(5) 0.092(2) Uani 1 1 d . . . H11 H 0.6936 0.0412 0.3408 0.11 Uiso 1 1 calc R . . C21 C 1.0104(9) -0.1944(7) 0.6203(6) 0.112(3) Uani 1 1 d . . . H21A H 0.9548 -0.2253 0.6802 0.134 Uiso 1 1 calc R . . H21B H 1.0709 -0.145 0.6355 0.134 Uiso 1 1 calc R . . C3 C 0.9539(9) 0.1201(6) 0.1505(5) 0.102(2) Uani 1 1 d U . . H3A H 0.9734 0.0496 0.1822 0.122 Uiso 1 1 calc R . . H3B H 0.912 0.1727 0.1991 0.122 Uiso 1 1 calc R . . C22 C 1.1066(10) -0.2860(7) 0.5657(7) 0.129(3) Uani 1 1 d . . . H22A H 1.0487 -0.3324 0.5453 0.193 Uiso 1 1 calc R . . H22B H 1.1596 -0.3283 0.606 0.193 Uiso 1 1 calc R . . H22C H 1.1727 -0.256 0.5108 0.193 Uiso 1 1 calc R . . H3N H 0.446(8) 0.252(6) 0.558(7) 0.193 Uiso 1 1 d 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 0.160(2) 0.0849(12) 0.0644(11) 0.0154(8) -0.0292(10) -0.0312(11) O7 0.100(3) 0.115(4) 0.091(3) 0.022(3) -0.027(3) -0.019(3) O5 0.146(5) 0.120(5) 0.144(6) -0.012(4) -0.065(4) -0.007(4) N1 0.133(5) 0.094(4) 0.080(4) 0.019(3) -0.032(3) -0.024(4) O4 0.128(4) 0.109(4) 0.095(4) -0.011(3) -0.029(3) -0.007(3) N2 0.137(5) 0.086(3) 0.056(3) 0.023(3) -0.031(3) -0.011(3) O1 0.192(6) 0.073(3) 0.085(3) 0.014(2) -0.030(3) -0.021(3) O6 0.165(6) 0.088(3) 0.156(6) -0.001(3) -0.077(4) 0.013(4) C4 0.123(6) 0.077(4) 0.074(4) 0.017(3) -0.040(4) -0.014(4) C25 0.109(6) 0.107(6) 0.093(5) 0.035(4) -0.026(4) -0.034(5) N6 0.109(4) 0.072(3) 0.070(3) 0.013(2) -0.026(3) -0.007(3) O3 0.137(5) 0.123(4) 0.098(4) 0.021(3) -0.038(3) 0.022(3) N4 0.121(5) 0.085(4) 0.067(3) 0.006(3) -0.027(3) -0.015(3) N3 0.104(4) 0.087(4) 0.070(4) 0.007(3) -0.020(3) -0.004(3) C26 0.117(7) 0.108(6) 0.108(7) 0.017(5) -0.008(5) -0.005(5) C13 0.102(5) 0.078(4) 0.073(4) -0.002(3) -0.022(3) -0.013(4) C17 0.204(12) 0.155(8) 0.203(12) 0.079(9) -0.071(10) 0.029(7) C23 0.121(7) 0.092(5) 0.096(6) 0.027(4) -0.036(5) 0.006(5) O8 0.151(5) 0.156(5) 0.099(4) 0.035(4) -0.015(4) 0.028(4) O2 0.195(6) 0.127(4) 0.072(3) 0.021(3) -0.037(3) -0.065(4) C24 0.103(5) 0.085(4) 0.069(4) 0.020(3) -0.026(3) -0.012(4) C8 0.114(6) 0.122(6) 0.088(5) 0.036(5) -0.041(4) -0.007(5) C12 0.093(5) 0.089(4) 0.064(4) 0.024(3) -0.024(3) -0.014(4) C14 0.100(5) 0.081(4) 0.071(4) 0.016(3) -0.025(3) -0.020(4) C29 0.097(5) 0.090(4) 0.082(4) 0.020(3) -0.024(4) -0.012(4) C1 0.146(8) 0.137(7) 0.100(6) 0.011(5) -0.029(5) -0.055(6) C7 0.118(6) 0.125(6) 0.072(5) 0.035(4) -0.040(4) -0.030(5) N5 0.129(5) 0.076(3) 0.078(4) 0.009(3) -0.031(3) -0.009(3) C5 0.153(7) 0.096(5) 0.064(4) 0.025(4) -0.036(4) -0.020(5) C30 0.125(7) 0.099(5) 0.098(6) 0.021(5) -0.029(5) -0.002(5) C28 0.154(8) 0.089(4) 0.095(6) 0.004(4) -0.035(5) -0.025(4) C16 0.104(5) 0.071(4) 0.061(4) 0.012(3) -0.025(3) -0.012(3) C6 0.131(6) 0.084(4) 0.072(4) 0.029(3) -0.046(4) -0.037(4) C18 0.291(10) 0.288(10) 0.297(10) -0.014(5) -0.076(5) -0.039(5) C10 0.108(5) 0.073(4) 0.065(4) 0.010(3) -0.028(3) -0.017(3) C27 0.161(9) 0.086(5) 0.106(6) 0.000(4) -0.012(6) -0.010(6) C9 0.109(6) 0.101(5) 0.077(5) 0.025(4) -0.028(4) -0.013(4) C31 0.112(7) 0.118(6) 0.156(9) 0.026(6) -0.015(6) -0.009(6) C2 0.127(5) 0.094(5) 0.084(5) 0.015(4) -0.039(4) -0.005(4) C15 0.117(6) 0.080(4) 0.070(4) 0.014(3) -0.033(4) -0.022(4) C20 0.132(6) 0.076(4) 0.081(5) 0.004(3) -0.035(4) -0.006(4) C19 0.146(7) 0.100(5) 0.071(5) -0.004(4) -0.027(4) -0.016(5) C11 0.124(6) 0.081(4) 0.071(4) 0.020(3) -0.030(4) -0.021(4) C21 0.128(7) 0.102(5) 0.101(6) 0.003(5) -0.028(5) -0.006(5) C3 0.144(6) 0.089(4) 0.066(4) 0.017(3) -0.030(3) 0.005(4) C22 0.138(7) 0.108(6) 0.133(7) -0.006(5) -0.036(6) 0.017(5) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O2 1.413(6) . ? S1 O1 1.446(6) . ? S1 N2 1.647(6) . ? S1 C6 1.746(8) . ? O7 C30 1.346(9) . ? O7 C29 1.408(9) . ? O5 C23 1.262(10) . ? O5 H5 0.82 . ? N1 C2 1.482(9) . ? N1 C5 1.492(9) . ? N1 C1 1.510(9) . ? O4 C13 1.224(8) . ? N2 C3 1.474(9) . ? N2 C4 1.490(8) . ? O6 C23 1.206(10) . ? C4 C5 1.512(9) . ? C4 H4A 0.97 . ? C4 H4B 0.97 . ? C25 C26 1.395(11) . ? C25 C24 1.402(10) . ? C25 H25 0.93 . ? N6 C12 1.290(8) . ? N6 C16 1.377(8) . ? O3 C9 1.403(9) . ? O3 C17 1.500(10) . ? N4 C14 1.343(9) . ? N4 N5 1.370(8) . ? N4 C19 1.443(8) . ? N3 C13 1.386(9) . ? N3 C12 1.404(9) . ? N3 H3N 0.901(10) . ? C26 C27 1.323(12) . ? C26 H26 0.93 . ? C13 C14 1.452(10) . ? C17 C18 1.539(2) . ? C17 H17A 0.97 . ? C17 H17B 0.97 . ? C23 C24 1.512(11) . ? O8 C30 1.203(10) . ? C24 C29 1.409(10) . ? C8 C7 1.338(10) . ? C8 C9 1.381(9) . ? C8 H8 0.93 . ? C12 C10 1.492(9) . ? C14 C16 1.382(9) . ? C29 C28 1.392(10) . ? C1 H1A 0.96 . ? C1 H1B 0.96 . ? C1 H1C 0.96 . ? C7 C6 1.418(11) . ? C7 H7 0.93 . ? N5 C15 1.333(8) . ? C5 H5A 0.97 . ? C5 H5B 0.97 . ? C30 C31 1.459(12) . ? C28 C27 1.390(12) . ? C28 H28 0.93 . ? C16 C15 1.405(10) . ? C6 C11 1.367(9) . ? C18 H18A 0.96 . ? C18 H18B 0.96 . ? C18 H18C 0.96 . ? C18 H18D 0.96 . ? C18 H18E 0.96 . ? C18 H18F 0.96 . ? C10 C11 1.363(9) . ? C10 C9 1.414(10) . ? C27 H27 0.93 . ? C31 H31A 0.96 . ? C31 H31B 0.96 . ? C31 H31C 0.96 . ? C2 C3 1.527(10) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C15 C20 1.502(10) . ? C20 C21 1.471(10) . ? C20 H20A 0.97 . ? C20 H20B 0.97 . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C11 H11 0.93 . ? C21 C22 1.504(11) . ? C21 H21A 0.97 . ? C21 H21B 0.97 . ? C3 H3A 0.97 . ? C3 H3B 0.97 . ? C22 H22A 0.96 . ? C22 H22B 0.96 . ? C22 H22C 0.96 . ? 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 O2 S1 O1 120.6(4) . . ? O2 S1 N2 104.9(3) . . ? O1 S1 N2 105.7(3) . . ? O2 S1 C6 109.5(4) . . ? O1 S1 C6 108.0(3) . . ? N2 S1 C6 107.5(3) . . ? C30 O7 C29 118.5(6) . . ? C23 O5 H5 109.5 . . ? C2 N1 C5 112.1(6) . . ? C2 N1 C1 109.3(7) . . ? C5 N1 C1 111.0(6) . . ? C3 N2 C4 110.4(5) . . ? C3 N2 S1 115.9(4) . . ? C4 N2 S1 116.9(5) . . ? N2 C4 C5 107.8(6) . . ? N2 C4 H4A 110.1 . . ? C5 C4 H4A 110.1 . . ? N2 C4 H4B 110.1 . . ? C5 C4 H4B 110.1 . . ? H4A C4 H4B 108.5 . . ? C26 C25 C24 121.3(8) . . ? C26 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C12 N6 C16 115.0(6) . . ? C9 O3 C17 123.7(6) . . ? C14 N4 N5 110.7(6) . . ? C14 N4 C19 129.6(7) . . ? N5 N4 C19 119.7(6) . . ? C13 N3 C12 125.5(6) . . ? C13 N3 H3N 121(7) . . ? C12 N3 H3N 114(7) . . ? C27 C26 C25 120.6(9) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? O4 C13 N3 121.5(7) . . ? O4 C13 C14 128.0(7) . . ? N3 C13 C14 110.5(6) . . ? O3 C17 C18 101.8(12) . . ? O3 C17 H17A 111.4 . . ? C18 C17 H17A 111.4 . . ? O3 C17 H17B 111.4 . . ? C18 C17 H17B 111.4 . . ? H17A C17 H17B 109.3 . . ? O6 C23 O5 127.3(9) . . ? O6 C23 C24 120.7(9) . . ? O5 C23 C24 112.0(7) . . ? C25 C24 C29 115.6(7) . . ? C25 C24 C23 120.9(7) . . ? C29 C24 C23 123.4(7) . . ? C7 C8 C9 121.0(7) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? N6 C12 N3 123.1(6) . . ? N6 C12 C10 119.1(6) . . ? N3 C12 C10 117.7(6) . . ? N4 C14 C16 107.7(6) . . ? N4 C14 C13 131.7(7) . . ? C16 C14 C13 120.5(6) . . ? C28 C29 O7 116.5(7) . . ? C28 C29 C24 122.8(8) . . ? O7 C29 C24 120.7(7) . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C8 C7 C6 120.2(7) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C15 N5 N4 106.1(6) . . ? N1 C5 C4 109.8(5) . . ? N1 C5 H5A 109.7 . . ? C4 C5 H5A 109.7 . . ? N1 C5 H5B 109.7 . . ? C4 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? O8 C30 O7 120.5(8) . . ? O8 C30 C31 127.1(9) . . ? O7 C30 C31 112.3(7) . . ? C27 C28 C29 117.5(8) . . ? C27 C28 H28 121.3 . . ? C29 C28 H28 121.3 . . ? N6 C16 C14 125.2(6) . . ? N6 C16 C15 129.6(6) . . ? C14 C16 C15 105.2(6) . . ? C11 C6 C7 117.9(7) . . ? C11 C6 S1 122.5(6) . . ? C7 C6 S1 119.6(5) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C18 H18D 109.5 . . ? H18A C18 H18D 141.1 . . ? H18B C18 H18D 56.3 . . ? H18C C18 H18D 56.3 . . ? C17 C18 H18E 109.5 . . ? H18A C18 H18E 56.3 . . ? H18B C18 H18E 141.1 . . ? H18C C18 H18E 56.3 . . ? H18D C18 H18E 109.5 . . ? C17 C18 H18F 109.5 . . ? H18A C18 H18F 56.3 . . ? H18B C18 H18F 56.3 . . ? H18C C18 H18F 141.1 . . ? H18D C18 H18F 109.5 . . ? H18E C18 H18F 109.5 . . ? C11 C10 C9 116.9(6) . . ? C11 C10 C12 117.3(7) . . ? C9 C10 C12 125.8(6) . . ? C26 C27 C28 122.1(9) . . ? C26 C27 H27 119 . . ? C28 C27 H27 119 . . ? C8 C9 O3 121.7(7) . . ? C8 C9 C10 120.4(7) . . ? O3 C9 C10 117.8(6) . . ? C30 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C30 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? N1 C2 C3 110.1(6) . . ? N1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? N5 C15 C16 110.3(6) . . ? N5 C15 C20 120.6(6) . . ? C16 C15 C20 129.0(6) . . ? C21 C20 C15 117.5(6) . . ? C21 C20 H20A 107.9 . . ? C15 C20 H20A 107.9 . . ? C21 C20 H20B 107.9 . . ? C15 C20 H20B 107.9 . . ? H20A C20 H20B 107.2 . . ? N4 C19 H19A 109.5 . . ? N4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C10 C11 C6 123.5(8) . . ? C10 C11 H11 118.2 . . ? C6 C11 H11 118.2 . . ? C20 C21 C22 115.8(7) . . ? C20 C21 H21A 108.3 . . ? C22 C21 H21A 108.3 . . ? C20 C21 H21B 108.3 . . ? C22 C21 H21B 108.3 . . ? H21A C21 H21B 107.4 . . ? N2 C3 C2 109.7(5) . . ? N2 C3 H3A 109.7 . . ? C2 C3 H3A 109.7 . . ? N2 C3 H3B 109.7 . . ? C2 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? # start Validation Reply Form _vrf_RINTA01_I ; PROBLEM: The value of Rint is greater than 0.25 RESPONSE: The investigated single crystal was a small-sized,brittle and poorly diffracting needle. Numerous datasets were collected on single crystals from different batches, whereof the one of the highest quality is reported herein. Attempts to collect a dataset of higher quality at low temperatures failed, as the fine needles tend to crack under the N2 flow. ; _vrf_PLAT020_I ; PROBLEM: The value of Rint is greater than 0.12 ......... 0.293 RESPONSE: The investigated single crystal was a small-sized,brittle and poorly diffracting needle. Numerous datasets were collected on single crystals from different batches, whereof the one of the highest quality is reported herein. Attempts to collect a dataset of higher quality at low temperatures failed, as the fine needles tend to crack under the N2 flow. ; _vrf_PLAT029_I ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.875 RESPONSE: The investigated single crystal was a small-sized,brittle and poorly diffracting needle. Numerous datasets were collected on single crystals from different batches, whereof the one of the highest quality is reported herein. Attempts to collect a dataset of higher quality at low temperatures failed, as the fine needles tend to crack under the N2 flow. ; # end Validation Reply Form _database_code_depnum_ccdc_archive 'CCDC 952210'