####################################################################### # # 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 _database_code_depnum_ccdc_archive 'CCDC 776943' #TrackingRef '- 2010_000113_CrystallographicData.cif' #============================================================================== _audit_creation_date 08-07-24 _audit_creation_method CRYSTALS_ver_12.86 _oxford_structure_analysis_title 5940 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 6.0756(2) _cell_length_b 6.6423(2) _cell_length_c 7.3505(2) _cell_angle_alpha 80.5318(12) _cell_angle_beta 84.2434(12) _cell_angle_gamma 89.0269(12) _cell_volume 291.120(15) _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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 1 # Given Formula = C9 H15 N1 O7 S1 # Dc = 1.60 Fooo = 148.00 Mu = 3.06 M = 281.29 # Found Formula = C9 H15 N1 O7 S1 # Dc = 1.60 FOOO = 148.00 Mu = 3.06 M = 281.29 _chemical_formula_sum 'C9 H15 N1 O7 S1' _chemical_formula_moiety 'C9 H15 N1 O7 S1' _chemical_compound_source . _chemical_formula_weight 281.29 _cell_measurement_reflns_used 1305 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.24 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.40 _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 148 _exptl_absorpt_coefficient_mu 0.306 # Sheldrick geometric approximatio 0.93 0.93 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.93 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 6964 _reflns_number_total 2545 _diffrn_reflns_av_R_equivalents 0.034 # Number of reflections with Friedels Law is 1324 # Number of reflections without Friedels Law is 2545 # Theoretical number of reflections is about 1337 _diffrn_reflns_theta_min 5.483 _diffrn_reflns_theta_max 27.494 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.944 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min -8 _reflns_limit_k_max 8 _reflns_limit_l_min -9 _reflns_limit_l_max 9 _oxford_diffrn_Wilson_B_factor 1.59 _oxford_diffrn_Wilson_scale 0.14 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.24 _refine_diff_density_max 0.20 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 2545 _refine_ls_number_restraints 3 _refine_ls_number_parameters 170 _oxford_refine_ls_R_factor_ref 0.0238 _refine_ls_wR_factor_ref 0.0570 _refine_ls_goodness_of_fit_ref 1.0079 _refine_ls_shift/su_max 0.000162 # The values computed from all data _oxford_reflns_number_all 2545 _refine_ls_R_factor_all 0.0238 _refine_ls_wR_factor_all 0.0570 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2498 _refine_ls_R_factor_gt 0.0232 _refine_ls_wR_factor_gt 0.0567 _refine_ls_abs_structure_Flack -0.02(4) _refine_ls_abs_structure_details 'Flack (1983), 1221 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.06P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens S1 S 0.54699(10) 0.54877(9) 0.33471(9) 0.0170 1.0000 Uani . . . . . . . O2 O 0.6667(2) 0.69721(18) 0.19999(16) 0.0252 1.0000 Uani . . . . . . . O3 O 0.34525(19) 0.6076(2) 0.42852(17) 0.0270 1.0000 Uani . . . . . . . N4 N 0.7041(2) 0.4484(2) 0.48566(17) 0.0186 1.0000 Uani . . . . . . . O5 O 0.49931(18) 0.36014(17) 0.23572(15) 0.0158 1.0000 Uani . . . . . . . C6 C 0.3972(2) 0.3950(2) 0.06135(19) 0.0150 1.0000 Uani . . . . . . . C7 C 0.1559(2) 0.4577(2) 0.0924(2) 0.0160 1.0000 Uani . . . . . . . O8 O 0.03994(18) 0.29475(16) 0.21780(15) 0.0167 1.0000 Uani . . . . . . . C9 C 0.0091(2) 0.1510(2) 0.09850(19) 0.0168 1.0000 Uani . . . . . . . O10 O -0.05633(18) 0.26698(17) -0.06649(16) 0.0193 1.0000 Uani . . . . . . . C11 C 0.0356(3) 0.4696(2) -0.0823(2) 0.0187 1.0000 Uani . . . . . . . C12 C 0.2299(2) 0.0400(2) 0.06958(19) 0.0152 1.0000 Uani . . . . . . . C13 C 0.4215(2) 0.1870(2) -0.00230(18) 0.0135 1.0000 Uani . . . . . . . O14 O 0.41299(17) 0.21196(16) -0.19912(15) 0.0156 1.0000 Uani . . . . . . . C15 C 0.3523(2) 0.0161(2) -0.23865(19) 0.0168 1.0000 Uani . . . . . . . O16 O 0.22897(19) -0.08447(16) -0.07127(15) 0.0184 1.0000 Uani . . . . . . . C17 C 0.5585(3) -0.1070(2) -0.2788(2) 0.0240 1.0000 Uani . . . . . . . C18 C 0.2047(3) 0.0484(2) -0.3941(2) 0.0225 1.0000 Uani . . . . . . . H41 H 0.643(3) 0.366(3) 0.587(3) 0.0259 1.0000 Uiso . . . . . . . H42 H 0.822(3) 0.398(3) 0.431(3) 0.0258 1.0000 Uiso . . . . . . . H61 H 0.4840 0.4992 -0.0278 0.0179 1.0000 Uiso R . . . . . . H71 H 0.1423 0.5799 0.1511 0.0192 1.0000 Uiso R . . . . . . H91 H -0.1140 0.0575 0.1602 0.0201 1.0000 Uiso R . . . . . . H111 H -0.0829 0.5677 -0.0786 0.0227 1.0000 Uiso R . . . . . . H112 H 0.1397 0.5002 -0.1982 0.0205 1.0000 Uiso R . . . . . . H121 H 0.2598 -0.0449 0.1866 0.0174 1.0000 Uiso R . . . . . . H131 H 0.5622 0.1258 0.0272 0.0149 1.0000 Uiso R . . . . . . H171 H 0.6537 -0.1153 -0.1757 0.0357 1.0000 Uiso R . . . . . . H172 H 0.6438 -0.0444 -0.3953 0.0359 1.0000 Uiso R . . . . . . H173 H 0.5215 -0.2457 -0.2928 0.0359 1.0000 Uiso R . . . . . . H181 H 0.0776 0.1344 -0.3519 0.0353 1.0000 Uiso R . . . . . . H182 H 0.2931 0.1240 -0.5057 0.0357 1.0000 Uiso R . . . . . . H183 H 0.1618 -0.0894 -0.4106 0.0344 1.0000 Uiso R . . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.01844(17) 0.01677(16) 0.01733(15) -0.00659(12) -0.00343(12) 0.00008(12) O2 0.0338(6) 0.0189(5) 0.0232(6) -0.0013(4) -0.0059(5) -0.0084(5) O3 0.0233(6) 0.0339(6) 0.0276(6) -0.0168(5) -0.0035(4) 0.0084(5) N4 0.0180(6) 0.0235(7) 0.0155(6) -0.0058(5) -0.0026(5) -0.0003(5) O5 0.0176(5) 0.0164(5) 0.0151(4) -0.0056(4) -0.0048(4) -0.0010(4) C6 0.0155(6) 0.0166(6) 0.0136(6) -0.0035(5) -0.0035(5) -0.0024(5) C7 0.0167(7) 0.0149(6) 0.0160(6) -0.0021(5) -0.0010(5) 0.0001(5) O8 0.0147(5) 0.0176(5) 0.0173(5) -0.0027(4) 0.0005(4) -0.0010(4) C9 0.0159(7) 0.0180(7) 0.0164(6) -0.0018(5) -0.0027(5) -0.0033(5) O10 0.0148(5) 0.0209(5) 0.0222(5) -0.0007(4) -0.0067(4) -0.0019(4) C11 0.0170(6) 0.0177(7) 0.0216(7) -0.0016(5) -0.0055(5) 0.0006(5) C12 0.0170(7) 0.0152(6) 0.0136(6) -0.0025(5) -0.0017(5) -0.0030(5) C13 0.0125(6) 0.0170(7) 0.0113(6) -0.0033(5) -0.0012(5) -0.0003(5) O14 0.0188(5) 0.0160(5) 0.0127(4) -0.0040(4) -0.0015(4) -0.0033(4) C15 0.0202(7) 0.0162(6) 0.0147(6) -0.0038(5) -0.0018(5) -0.0032(5) O16 0.0237(5) 0.0168(5) 0.0151(5) -0.0037(4) -0.0016(4) -0.0055(4) C17 0.0269(8) 0.0239(8) 0.0224(7) -0.0086(6) -0.0014(6) 0.0036(6) C18 0.0274(8) 0.0236(7) 0.0180(7) -0.0044(6) -0.0085(6) -0.0030(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.597(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . O2 . 1.4284(11) yes S1 . O3 . 1.4259(11) yes S1 . N4 . 1.5921(12) yes S1 . O5 . 1.5930(10) yes N4 . H41 . 0.90(2) no N4 . H42 . 0.87(2) no O5 . C6 . 1.4622(16) yes C6 . C7 . 1.5227(18) yes C6 . C13 . 1.5300(18) yes C6 . H61 . 0.990 no C7 . O8 . 1.4438(16) yes C7 . C11 . 1.530(2) yes C7 . H71 . 0.979 no O8 . C9 . 1.4251(17) yes C9 . O10 . 1.4147(16) yes C9 . C12 . 1.5327(18) yes C9 . H91 . 1.003 no O10 . C11 . 1.4483(17) yes C11 . H111 . 0.965 no C11 . H112 . 1.003 no C12 . C13 . 1.5276(18) yes C12 . O16 . 1.4277(16) yes C12 . H121 . 0.979 no C13 . O14 . 1.4350(15) yes C13 . H131 . 0.970 no O14 . C15 . 1.4404(16) yes C15 . O16 . 1.4432(17) yes C15 . C17 . 1.515(2) yes C15 . C18 . 1.5081(19) yes C17 . H171 . 0.992 no C17 . H172 . 0.988 no C17 . H173 . 0.976 no C18 . H181 . 1.007 no C18 . H182 . 0.999 no C18 . H183 . 0.985 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 . S1 . O3 . 118.91(7) yes O2 . S1 . N4 . 110.04(7) yes O3 . S1 . N4 . 108.49(7) yes O2 . S1 . O5 . 107.49(6) yes O3 . S1 . O5 . 108.79(6) yes N4 . S1 . O5 . 101.75(6) yes S1 . N4 . H41 . 118.4(13) no S1 . N4 . H42 . 109.7(13) no H41 . N4 . H42 . 114.3(18) no S1 . O5 . C6 . 119.67(8) yes O5 . C6 . C7 . 111.03(11) yes O5 . C6 . C13 . 102.57(10) yes C7 . C6 . C13 . 112.05(11) yes O5 . C6 . H61 . 108.9 no C7 . C6 . H61 . 111.7 no C13 . C6 . H61 . 110.1 no C6 . C7 . O8 . 108.16(10) yes C6 . C7 . C11 . 112.49(12) yes O8 . C7 . C11 . 102.51(11) yes C6 . C7 . H71 . 110.9 no O8 . C7 . H71 . 107.4 no C11 . C7 . H71 . 114.7 no C7 . O8 . C9 . 102.00(10) yes O8 . C9 . O10 . 105.63(10) yes O8 . C9 . C12 . 107.19(11) yes O10 . C9 . C12 . 113.24(11) yes O8 . C9 . H91 . 107.3 no O10 . C9 . H91 . 109.9 no C12 . C9 . H91 . 113.1 no C9 . O10 . C11 . 107.24(10) yes C7 . C11 . O10 . 103.52(11) yes C7 . C11 . H111 . 109.3 no O10 . C11 . H111 . 109.4 no C7 . C11 . H112 . 112.0 no O10 . C11 . H112 . 109.9 no H111 . C11 . H112 . 112.4 no C9 . C12 . C13 . 112.49(11) yes C9 . C12 . O16 . 111.96(11) yes C13 . C12 . O16 . 103.22(10) yes C9 . C12 . H121 . 109.0 no C13 . C12 . H121 . 110.5 no O16 . C12 . H121 . 109.5 no C6 . C13 . C12 . 114.59(11) yes C6 . C13 . O14 . 109.68(10) yes C12 . C13 . O14 . 101.99(10) yes C6 . C13 . H131 . 110.1 no C12 . C13 . H131 . 111.4 no O14 . C13 . H131 . 108.7 no C13 . O14 . C15 . 106.32(10) yes O14 . C15 . O16 . 105.45(10) yes O14 . C15 . C17 . 109.85(12) yes O16 . C15 . C17 . 109.08(11) yes O14 . C15 . C18 . 108.95(11) yes O16 . C15 . C18 . 109.48(12) yes C17 . C15 . C18 . 113.69(12) yes C15 . O16 . C12 . 109.36(10) yes C15 . C17 . H171 . 110.1 no C15 . C17 . H172 . 110.9 no H171 . C17 . H172 . 109.0 no C15 . C17 . H173 . 111.3 no H171 . C17 . H173 . 108.3 no H172 . C17 . H173 . 107.2 no C15 . C18 . H181 . 105.8 no C15 . C18 . H182 . 107.2 no H181 . C18 . H182 . 110.6 no C15 . C18 . H183 . 105.5 no H181 . C18 . H183 . 114.2 no H182 . C18 . H183 . 112.8 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N4 . H41 . O14 1_556 163 0.90(2) 2.13(2) 3.006(2) yes N4 . H42 . O8 1_655 160 0.87(2) 2.14(2) 2.977(2) yes C7 . H71 . O3 . 121 0.98 2.52 3.137(2) yes C13 . H131 . O10 1_655 129 0.97 2.50 3.201(2) yes C18 . H181 . O10 . 137 1.01 2.47 3.276(2) yes C18 . H182 . O5 1_554 171 1.00 2.50 3.492(2) yes _chemical_name_common .