Supplementary Material (ESI) for Chemical Communications
This journal is (c) The Royal Society of Chemistry 2010
#==============================================================================
data_5
_database_code_depnum_ccdc_archive 'CCDC 757478'
#TrackingRef 'CrystallographicData.cif'
#==============================================================================
_audit_creation_date 09-02-23
_audit_creation_method CRYSTALS_ver_12.86
_ccdc_journal_depnumber 'CCDC 757478'
_oxford_structure_analysis_title 3-61
_chemical_name_systematic .
_chemical_melting_point 360
_cell_length_a 6.5055(2)
_cell_length_b 22.4224(6)
_cell_length_c 8.9905(3)
_cell_angle_alpha 90
_cell_angle_beta 108.6921(10)
_cell_angle_gamma 90
_cell_volume 1242.26(7)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 1 21/n 1 '
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
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 4
# Given Formula = C10 H17 N1 O5 S1
# Dc = 1.41 Fooo = 560.00 Mu = 2.70 M = 263.31
# Found Formula = C10 H17 N1 O5 S1
# Dc = 1.41 FOOO = 560.00 Mu = 2.70 M = 263.31
_chemical_formula_sum 'C10 H17 N1 O5 S1'
_chemical_formula_moiety 'C10 H17 N1 O5 S1'
_chemical_compound_source .
_chemical_formula_weight 263.31
_cell_measurement_reflns_used 2767
_cell_measurement_theta_min 5
_cell_measurement_theta_max 27
_cell_measurement_temperature 150
_exptl_crystal_description plate
_exptl_crystal_colour clear_pale_colourless
_exptl_crystal_size_min 0.14
_exptl_crystal_size_mid 0.30
_exptl_crystal_size_max 0.34
_exptl_crystal_density_diffrn 1.408
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 560
_exptl_absorpt_coefficient_mu 0.270
# Sheldrick geometric approximatio 0.92 0.96
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.92
_exptl_absorpt_correction_T_max 0.96
# 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 12353
_reflns_number_total 2829
_diffrn_reflns_av_R_equivalents 0.035
# Number of reflections with Friedels Law is 2829
# Number of reflections without Friedels Law is 5230
# Theoretical number of reflections is about 2852
_diffrn_reflns_theta_min 5.122
_diffrn_reflns_theta_max 27.494
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full 26.944
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -29
_diffrn_reflns_limit_k_max 27
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 11
_reflns_limit_h_min -8
_reflns_limit_h_max 7
_reflns_limit_k_min 0
_reflns_limit_k_max 28
_reflns_limit_l_min 0
_reflns_limit_l_max 11
_oxford_diffrn_Wilson_B_factor 1.95
_oxford_diffrn_Wilson_scale 2.68
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.47
_refine_diff_density_max 0.41
# 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>-10.0\s(I)
_refine_ls_number_reflns 2829
_refine_ls_number_restraints 0
_refine_ls_number_parameters 154
_oxford_refine_ls_R_factor_ref 0.0616
_refine_ls_wR_factor_ref 0.0967
_refine_ls_goodness_of_fit_ref 0.8963
_refine_ls_shift/su_max 0.000410
# The values computed from all data
_oxford_reflns_number_all 2829
_refine_ls_R_factor_all 0.0616
_refine_ls_wR_factor_all 0.0967
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 2141
_refine_ls_R_factor_gt 0.0391
_refine_ls_wR_factor_gt 0.0864
# 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 .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment constr # 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^) + ( 0.04P)^2^ + 1.06P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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 0.43897(7) 0.230689(19) 0.81923(5) 0.0208 1.0000 Uani . . . . . . .
O2 O 0.3969(2) 0.20512(6) 0.66680(14) 0.0273 1.0000 Uani . . . . . . .
O3 O 0.21572(19) 0.25962(6) 0.81142(15) 0.0277 1.0000 Uani . . . . . . .
C4 C 0.2186(3) 0.30635(9) 0.9267(2) 0.0302 1.0000 Uani . . . . . . .
C5 C 0.2203(3) 0.36660(9) 0.8519(2) 0.0293 1.0000 Uani . . . . . . .
C6 C 0.4320(3) 0.38515(8) 0.8263(2) 0.0228 1.0000 Uani . . . . . . .
O7 O 0.5880(2) 0.39669(5) 0.98185(14) 0.0258 1.0000 Uani . . . . . . .
C8 C 0.7015(3) 0.44801(8) 1.0020(2) 0.0259 1.0000 Uani . . . . . . .
O9 O 0.6738(2) 0.48550(6) 0.90188(17) 0.0389 1.0000 Uani . . . . . . .
C10 C 0.8623(3) 0.45184(9) 1.1624(2) 0.0324 1.0000 Uani . . . . . . .
C11 C 0.5361(3) 0.33923(7) 0.7508(2) 0.0195 1.0000 Uani . . . . . . .
N12 N 0.6065(2) 0.28560(6) 0.84349(16) 0.0195 1.0000 Uani . . . . . . .
C13 C 0.5716(3) 0.34489(8) 0.6147(2) 0.0223 1.0000 Uani . . . . . . .
C14 C 0.5099(3) 0.39690(8) 0.5029(2) 0.0261 1.0000 Uani . . . . . . .
C15 C 0.4350(3) 0.37588(9) 0.3321(2) 0.0308 1.0000 Uani . . . . . . .
C16 C 0.7048(4) 0.43888(9) 0.5321(2) 0.0346 1.0000 Uani . . . . . . .
O17 O 0.5160(2) 0.19307(6) 0.95307(14) 0.0277 1.0000 Uani . . . . . . .
H41 H 0.3433 0.3004 1.0201 0.0367 1.0000 Uiso R . . . . . .
H42 H 0.0879 0.3004 0.9512 0.0370 1.0000 Uiso R . . . . . .
H51 H 0.1873 0.3962 0.9180 0.0354 1.0000 Uiso R . . . . . .
H52 H 0.1075 0.3668 0.7521 0.0356 1.0000 Uiso R . . . . . .
H61 H 0.4065 0.4217 0.7645 0.0257 1.0000 Uiso R . . . . . .
H103 H 0.9898 0.4702 1.1570 0.0500 1.0000 Uiso R . . . . . .
H102 H 0.8018 0.4760 1.2245 0.0503 1.0000 Uiso R . . . . . .
H101 H 0.8925 0.4143 1.2117 0.0492 1.0000 Uiso R . . . . . .
H131 H 0.6459 0.3137 0.5857 0.0280 1.0000 Uiso R . . . . . .
H141 H 0.3897 0.4182 0.5213 0.0316 1.0000 Uiso R . . . . . .
H152 H 0.3920 0.4096 0.2627 0.0451 1.0000 Uiso R . . . . . .
H151 H 0.5535 0.3548 0.3097 0.0455 1.0000 Uiso R . . . . . .
H153 H 0.3138 0.3488 0.3122 0.0462 1.0000 Uiso R . . . . . .
H162 H 0.6640 0.4716 0.4585 0.0525 1.0000 Uiso R . . . . . .
H163 H 0.7454 0.4542 0.6366 0.0524 1.0000 Uiso R . . . . . .
H161 H 0.8281 0.4182 0.5182 0.0521 1.0000 Uiso R . . . . . .
H121 H 0.6985 0.2873 0.9244 0.0249 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 0.0225(2) 0.0200(2) 0.0178(2) 0.00097(17) 0.00359(17) -0.00235(17)
O2 0.0339(7) 0.0248(7) 0.0187(7) -0.0038(5) 0.0019(5) -0.0020(6)
O3 0.0206(6) 0.0302(7) 0.0309(7) -0.0023(6) 0.0062(5) -0.0041(5)
C4 0.0284(10) 0.0374(11) 0.0296(11) -0.0015(9) 0.0162(8) -0.0009(8)
C5 0.0289(10) 0.0316(10) 0.0294(10) -0.0014(8) 0.0123(8) 0.0057(8)
C6 0.0281(9) 0.0210(8) 0.0182(9) 0.0010(7) 0.0060(7) 0.0016(7)
O7 0.0354(7) 0.0211(6) 0.0194(7) -0.0010(5) 0.0069(5) -0.0039(5)
C8 0.0302(10) 0.0226(9) 0.0301(11) -0.0010(8) 0.0169(8) -0.0008(8)
O9 0.0475(9) 0.0326(8) 0.0362(9) 0.0096(7) 0.0128(7) -0.0090(7)
C10 0.0368(11) 0.0299(10) 0.0302(11) -0.0032(8) 0.0104(9) -0.0045(9)
C11 0.0196(8) 0.0184(8) 0.0191(9) 0.0015(7) 0.0041(7) -0.0011(7)
N12 0.0183(7) 0.0211(7) 0.0156(7) 0.0010(6) 0.0008(6) -0.0011(6)
C13 0.0224(9) 0.0210(8) 0.0243(9) 0.0021(7) 0.0086(7) 0.0027(7)
C14 0.0317(10) 0.0247(9) 0.0250(10) 0.0051(8) 0.0133(8) 0.0057(8)
C15 0.0340(11) 0.0332(10) 0.0240(10) 0.0059(8) 0.0077(8) 0.0002(9)
C16 0.0514(13) 0.0259(10) 0.0285(11) 0.0019(8) 0.0155(9) -0.0054(9)
O17 0.0332(7) 0.0257(7) 0.0212(7) 0.0069(5) 0.0043(5) -0.0042(6)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.6067(14)
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 . 1.4287(13) yes
S1 . O3 . 1.5715(13) yes
S1 . N12 . 1.6119(14) yes
S1 . O17 . 1.4227(13) yes
O3 . C4 . 1.470(2) yes
C4 . C5 . 1.511(3) yes
C4 . H41 . 0.972 no
C4 . H42 . 0.954 no
C5 . C6 . 1.525(3) yes
C5 . H51 . 0.959 no
C5 . H52 . 0.960 no
C6 . O7 . 1.464(2) yes
C6 . C11 . 1.508(2) yes
C6 . H61 . 0.974 no
O7 . C8 . 1.348(2) yes
C8 . O9 . 1.202(2) yes
C8 . C10 . 1.488(3) yes
C10 . H103 . 0.941 no
C10 . H102 . 0.950 no
C10 . H101 . 0.942 no
C11 . N12 . 1.451(2) yes
C11 . C13 . 1.322(2) yes
N12 . H121 . 0.781 no
C13 . C14 . 1.508(2) yes
C13 . H131 . 0.933 no
C14 . C15 . 1.528(3) yes
C14 . C16 . 1.533(3) yes
C14 . H141 . 0.974 no
C15 . H152 . 0.963 no
C15 . H151 . 0.979 no
C15 . H153 . 0.965 no
C16 . H162 . 0.967 no
C16 . H163 . 0.954 no
C16 . H161 . 0.969 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 . 103.44(7) yes
O2 . S1 . N12 . 110.47(8) yes
O3 . S1 . N12 . 105.41(7) yes
O2 . S1 . O17 . 118.73(8) yes
O3 . S1 . O17 . 110.63(8) yes
N12 . S1 . O17 . 107.40(8) yes
S1 . O3 . C4 . 117.39(11) yes
O3 . C4 . C5 . 108.90(15) yes
O3 . C4 . H41 . 109.3 no
C5 . C4 . H41 . 112.6 no
O3 . C4 . H42 . 104.6 no
C5 . C4 . H42 . 111.2 no
H41 . C4 . H42 . 109.9 no
C4 . C5 . C6 . 116.54(16) yes
C4 . C5 . H51 . 107.9 no
C6 . C5 . H51 . 107.3 no
C4 . C5 . H52 . 107.9 no
C6 . C5 . H52 . 108.3 no
H51 . C5 . H52 . 108.7 no
C5 . C6 . O7 . 106.69(14) yes
C5 . C6 . C11 . 116.05(15) yes
O7 . C6 . C11 . 106.07(14) yes
C5 . C6 . H61 . 108.6 no
O7 . C6 . H61 . 109.6 no
C11 . C6 . H61 . 109.6 no
C6 . O7 . C8 . 117.48(14) yes
O7 . C8 . O9 . 123.52(18) yes
O7 . C8 . C10 . 111.35(16) yes
O9 . C8 . C10 . 125.13(18) yes
C8 . C10 . H103 . 109.5 no
C8 . C10 . H102 . 107.9 no
H103 . C10 . H102 . 108.6 no
C8 . C10 . H101 . 112.4 no
H103 . C10 . H101 . 111.2 no
H102 . C10 . H101 . 107.2 no
C6 . C11 . N12 . 114.31(14) yes
C6 . C11 . C13 . 126.01(16) yes
N12 . C11 . C13 . 119.65(15) yes
C11 . N12 . S1 . 118.70(11) yes
C11 . N12 . H121 . 120.1 no
S1 . N12 . H121 . 116.5 no
C11 . C13 . C14 . 127.10(16) yes
C11 . C13 . H131 . 116.5 no
C14 . C13 . H131 . 116.4 no
C13 . C14 . C15 . 111.24(15) yes
C13 . C14 . C16 . 109.37(16) yes
C15 . C14 . C16 . 109.98(15) yes
C13 . C14 . H141 . 108.8 no
C15 . C14 . H141 . 107.9 no
C16 . C14 . H141 . 109.5 no
C14 . C15 . H152 . 110.0 no
C14 . C15 . H151 . 109.7 no
H152 . C15 . H151 . 109.2 no
C14 . C15 . H153 . 111.0 no
H152 . C15 . H153 . 108.9 no
H151 . C15 . H153 . 108.0 no
C14 . C16 . H162 . 108.6 no
C14 . C16 . H163 . 110.1 no
H162 . C16 . H163 . 109.2 no
C14 . C16 . H161 . 111.0 no
H162 . C16 . H161 . 109.3 no
H163 . C16 . H161 . 108.6 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
N12 . H121 . O2 4_555 168 0.78 2.15 2.923(3) yes
_chemical_name_common .
#==============================================================================
data_12
_database_code_depnum_ccdc_archive 'CCDC 757479'
#TrackingRef 'CrystallographicData.cif'
#==============================================================================
_audit_creation_date 09-02-26
_audit_creation_method CRYSTALS_ver_12.86
_ccdc_journal_depnumber 'CCDC 757479'
_oxford_structure_analysis_title 3-96
_chemical_name_systematic .
_chemical_melting_point 352
_cell_length_a 7.6562(2)
_cell_length_b 8.7683(2)
_cell_length_c 10.0293(2)
_cell_angle_alpha 77.2922(12)
_cell_angle_beta 78.9430(12)
_cell_angle_gamma 69.3572(10)
_cell_volume 609.79(2)
_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
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'
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'
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'
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 2
# Given Formula = C10 H17 N1 O5 S1
# Dc = 1.43 Fooo = 280.00 Mu = 2.75 M = 263.31
# Found Formula = C10 H17 N1 O5 S1
# Dc = 1.43 FOOO = 280.00 Mu = 2.75 M = 263.31
_chemical_formula_sum 'C10 H17 N1 O5 S1'
_chemical_formula_moiety 'C10 H17 N1 O5 S1'
_chemical_compound_source .
_chemical_formula_weight 263.31
_cell_measurement_reflns_used 2438
_cell_measurement_theta_min 5
_cell_measurement_theta_max 27
_cell_measurement_temperature 150
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.34
_exptl_crystal_size_mid 0.62
_exptl_crystal_size_max 0.64
_exptl_crystal_density_diffrn 1.434
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 280
_exptl_absorpt_coefficient_mu 0.275
# Sheldrick geometric approximatio 0.84 0.91
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.77
_exptl_absorpt_correction_T_max 0.91
# 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 8663
_reflns_number_total 2766
_diffrn_reflns_av_R_equivalents 0.021
# Number of reflections with Friedels Law is 2766
# Number of reflections without Friedels Law is 4705
# Theoretical number of reflections is about 2804
_diffrn_reflns_theta_min 5.245
_diffrn_reflns_theta_max 27.507
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full 26.957
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 13
_reflns_limit_h_min -9
_reflns_limit_h_max 9
_reflns_limit_k_min -10
_reflns_limit_k_max 11
_reflns_limit_l_min 0
_reflns_limit_l_max 13
_oxford_diffrn_Wilson_B_factor 1.62
_oxford_diffrn_Wilson_scale 0.20
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.40
_refine_diff_density_max 0.34
# 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>-10.0\s(I)
_refine_ls_number_reflns 2766
_refine_ls_number_restraints 0
_refine_ls_number_parameters 154
_oxford_refine_ls_R_factor_ref 0.0360
_refine_ls_wR_factor_ref 0.0856
_refine_ls_goodness_of_fit_ref 0.9945
_refine_ls_shift/su_max 0.000718
# The values computed from all data
_oxford_reflns_number_all 2766
_refine_ls_R_factor_all 0.0360
_refine_ls_wR_factor_all 0.0856
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 2569
_refine_ls_R_factor_gt 0.0330
_refine_ls_wR_factor_gt 0.0837
# 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 .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment constr # 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^) + ( 0.04P)^2^ + 0.44P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
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 1.25872(4) 0.18058(4) 0.25842(3) 0.0206 1.0000 Uani . . . . . . .
O2 O 1.24115(13) 0.34868(12) 0.30129(10) 0.0226 1.0000 Uani . . . . . . .
C3 C 1.07082(19) 0.48943(17) 0.27283(15) 0.0217 1.0000 Uani . . . . . . .
C4 C 0.89922(19) 0.46546(16) 0.36728(13) 0.0184 1.0000 Uani . . . . . . .
C5 C 0.79899(17) 0.37088(15) 0.31638(13) 0.0154 1.0000 Uani . . . . . . .
C6 C 0.74017(18) 0.24082(16) 0.42554(13) 0.0172 1.0000 Uani . . . . . . .
C7 C 0.90443(17) 0.18942(15) 0.31804(12) 0.0143 1.0000 Uani . . . . . . .
N8 N 1.09262(15) 0.11658(13) 0.35343(11) 0.0165 1.0000 Uani . . . . . . .
O9 O 0.87425(13) 0.12051(11) 0.21160(9) 0.0157 1.0000 Uani . . . . . . .
C10 C 0.86448(17) -0.03495(15) 0.24729(13) 0.0157 1.0000 Uani . . . . . . .
O11 O 0.88650(14) -0.11652(11) 0.36064(9) 0.0211 1.0000 Uani . . . . . . .
C12 C 0.8284(2) -0.09141(16) 0.12831(13) 0.0198 1.0000 Uani . . . . . . .
C13 C 0.67552(18) 0.46819(16) 0.20456(13) 0.0183 1.0000 Uani . . . . . . .
C14 C 0.50378(19) 0.60688(17) 0.25373(15) 0.0214 1.0000 Uani . . . . . . .
C15 C 0.3923(2) 0.7134(2) 0.13704(17) 0.0315 1.0000 Uani . . . . . . .
O16 O 1.22226(15) 0.21343(14) 0.11920(10) 0.0286 1.0000 Uani . . . . . . .
O17 O 1.43336(14) 0.07063(14) 0.30013(13) 0.0328 1.0000 Uani . . . . . . .
H31 H 1.0978 0.5852 0.2900 0.0250 1.0000 Uiso R . . . . . .
H32 H 1.0571 0.5017 0.1782 0.0252 1.0000 Uiso R . . . . . .
H41 H 0.9391 0.4063 0.4589 0.0231 1.0000 Uiso R . . . . . .
H42 H 0.8107 0.5782 0.3753 0.0237 1.0000 Uiso R . . . . . .
H61 H 0.7656 0.2247 0.5229 0.0202 1.0000 Uiso R . . . . . .
H62 H 0.6279 0.2140 0.4214 0.0215 1.0000 Uiso R . . . . . .
H122 H 0.7763 -0.1800 0.1612 0.0333 1.0000 Uiso R . . . . . .
H121 H 0.9485 -0.1301 0.0676 0.0327 1.0000 Uiso R . . . . . .
H123 H 0.7464 0.0004 0.0717 0.0321 1.0000 Uiso R . . . . . .
H131 H 0.7491 0.5149 0.1304 0.0216 1.0000 Uiso R . . . . . .
H132 H 0.6300 0.3936 0.1725 0.0217 1.0000 Uiso R . . . . . .
H141 H 0.5460 0.6749 0.2981 0.0246 1.0000 Uiso R . . . . . .
H142 H 0.4236 0.5577 0.3232 0.0239 1.0000 Uiso R . . . . . .
H152 H 0.2809 0.7994 0.1744 0.0439 1.0000 Uiso R . . . . . .
H153 H 0.4731 0.7628 0.0626 0.0437 1.0000 Uiso R . . . . . .
H151 H 0.3482 0.6450 0.0969 0.0432 1.0000 Uiso R . . . . . .
H81 H 1.1093 0.0675 0.4403 0.0222 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 0.01662(17) 0.02443(19) 0.02314(18) -0.00914(13) 0.00000(12) -0.00781(13)
O2 0.0201(5) 0.0236(5) 0.0287(5) -0.0077(4) -0.0042(4) -0.0103(4)
C3 0.0233(7) 0.0191(6) 0.0255(7) -0.0037(5) -0.0053(5) -0.0091(5)
C4 0.0213(6) 0.0167(6) 0.0199(6) -0.0067(5) -0.0039(5) -0.0065(5)
C5 0.0167(6) 0.0142(6) 0.0158(6) -0.0037(4) -0.0029(4) -0.0044(5)
C6 0.0179(6) 0.0181(6) 0.0163(6) -0.0047(5) -0.0003(5) -0.0066(5)
C7 0.0159(6) 0.0155(6) 0.0140(6) -0.0051(4) -0.0032(4) -0.0059(5)
N8 0.0166(5) 0.0174(5) 0.0165(5) -0.0027(4) -0.0044(4) -0.0055(4)
O9 0.0207(4) 0.0150(4) 0.0142(4) -0.0040(3) -0.0036(3) -0.0077(3)
C10 0.0153(6) 0.0147(6) 0.0179(6) -0.0046(4) -0.0024(4) -0.0045(4)
O11 0.0295(5) 0.0179(5) 0.0176(5) -0.0016(4) -0.0067(4) -0.0085(4)
C12 0.0265(7) 0.0182(6) 0.0178(6) -0.0047(5) -0.0059(5) -0.0085(5)
C13 0.0183(6) 0.0183(6) 0.0183(6) -0.0033(5) -0.0039(5) -0.0050(5)
C14 0.0175(6) 0.0198(6) 0.0257(7) -0.0036(5) -0.0025(5) -0.0048(5)
C15 0.0201(7) 0.0305(8) 0.0350(8) 0.0062(6) -0.0049(6) -0.0035(6)
O16 0.0329(6) 0.0400(6) 0.0184(5) -0.0097(4) 0.0040(4) -0.0196(5)
O17 0.0159(5) 0.0329(6) 0.0493(7) -0.0139(5) -0.0053(4) -0.0028(4)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 2.280(19)
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 . 1.5788(10) yes
S1 . N8 . 1.6258(11) yes
S1 . O16 . 1.4234(11) yes
S1 . O17 . 1.4214(11) yes
O2 . C3 . 1.4691(16) yes
C3 . C4 . 1.5157(19) yes
C3 . H31 . 0.988 no
C3 . H32 . 0.953 no
C4 . C5 . 1.5239(17) yes
C4 . H41 . 0.997 no
C4 . H42 . 0.992 no
C5 . C6 . 1.5250(17) yes
C5 . C7 . 1.5071(17) yes
C5 . C13 . 1.5153(17) yes
C6 . C7 . 1.4971(17) yes
C6 . H61 . 1.002 no
C6 . H62 . 0.978 no
C7 . N8 . 1.4344(15) yes
C7 . O9 . 1.4266(14) yes
N8 . H81 . 0.894 no
O9 . C10 . 1.3559(15) yes
C10 . O11 . 1.2097(16) yes
C10 . C12 . 1.4926(17) yes
C12 . H122 . 0.962 no
C12 . H121 . 0.994 no
C12 . H123 . 0.972 no
C13 . C14 . 1.5292(18) yes
C13 . H131 . 0.952 no
C13 . H132 . 0.974 no
C14 . C15 . 1.520(2) yes
C14 . H141 . 0.983 no
C14 . H142 . 0.969 no
C15 . H152 . 0.992 no
C15 . H153 . 0.998 no
C15 . H151 . 0.968 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 . N8 . 107.09(6) yes
O2 . S1 . O16 . 108.40(6) yes
N8 . S1 . O16 . 107.32(6) yes
O2 . S1 . O17 . 103.83(6) yes
N8 . S1 . O17 . 107.74(6) yes
O16 . S1 . O17 . 121.66(7) yes
S1 . O2 . C3 . 117.18(8) yes
O2 . C3 . C4 . 111.44(11) yes
O2 . C3 . H31 . 104.4 no
C4 . C3 . H31 . 110.6 no
O2 . C3 . H32 . 107.6 no
C4 . C3 . H32 . 111.9 no
H31 . C3 . H32 . 110.5 no
C3 . C4 . C5 . 115.10(11) yes
C3 . C4 . H41 . 108.1 no
C5 . C4 . H41 . 109.1 no
C3 . C4 . H42 . 105.8 no
C5 . C4 . H42 . 108.6 no
H41 . C4 . H42 . 110.1 no
C4 . C5 . C6 . 115.04(10) yes
C4 . C5 . C7 . 115.26(10) yes
C6 . C5 . C7 . 59.17(8) yes
C4 . C5 . C13 . 115.72(10) yes
C6 . C5 . C13 . 119.71(11) yes
C7 . C5 . C13 . 120.16(10) yes
C5 . C6 . C7 . 59.82(8) yes
C5 . C6 . H61 . 120.0 no
C7 . C6 . H61 . 118.1 no
C5 . C6 . H62 . 121.1 no
C7 . C6 . H62 . 117.3 no
H61 . C6 . H62 . 111.5 no
C5 . C7 . C6 . 61.01(8) yes
C5 . C7 . N8 . 121.46(10) yes
C6 . C7 . N8 . 121.09(10) yes
C5 . C7 . O9 . 115.34(10) yes
C6 . C7 . O9 . 116.14(10) yes
N8 . C7 . O9 . 112.67(10) yes
C7 . N8 . S1 . 119.13(9) yes
C7 . N8 . H81 . 118.6 no
S1 . N8 . H81 . 118.3 no
C7 . O9 . C10 . 116.32(9) yes
O9 . C10 . O11 . 123.50(11) yes
O9 . C10 . C12 . 111.17(10) yes
O11 . C10 . C12 . 125.31(12) yes
C10 . C12 . H122 . 109.9 no
C10 . C12 . H121 . 109.3 no
H122 . C12 . H121 . 109.8 no
C10 . C12 . H123 . 110.5 no
H122 . C12 . H123 . 111.6 no
H121 . C12 . H123 . 105.7 no
C5 . C13 . C14 . 113.20(11) yes
C5 . C13 . H131 . 108.5 no
C14 . C13 . H131 . 108.9 no
C5 . C13 . H132 . 109.0 no
C14 . C13 . H132 . 107.6 no
H131 . C13 . H132 . 109.7 no
C13 . C14 . C15 . 112.37(12) yes
C13 . C14 . H141 . 108.8 no
C15 . C14 . H141 . 110.4 no
C13 . C14 . H142 . 108.4 no
C15 . C14 . H142 . 109.4 no
H141 . C14 . H142 . 107.3 no
C14 . C15 . H152 . 109.3 no
C14 . C15 . H153 . 110.9 no
H152 . C15 . H153 . 111.8 no
C14 . C15 . H151 . 109.1 no
H152 . C15 . H151 . 108.1 no
H153 . C15 . H151 . 107.4 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
N8 . H81 . O11 2_756 143 0.89 2.14 2.902(2) yes
_chemical_name_common .
data_II
_database_code_depnum_ccdc_archive 'CCDC 763606'
_audit_creation_method CRYSTALS_ver_12.90
_chemical_name_systematic
;
;
_chemical_formula_moiety 'C9 H15 N1 O3 S'
_chemical_formula_sum 'C9 H15 N1 O3 S'
_chemical_formula_weight 217.29
_chemical_melting_point 331
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 1 21/c 1 '
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
_cell_length_a 13.8594(2)
_cell_length_b 10.5243(2)
_cell_length_c 19.9230(3)
_cell_angle_alpha 90
_cell_angle_beta 132.0439(7)
_cell_angle_gamma 90
_cell_volume 2158.07(7)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 4694
_cell_measurement_theta_min 5
_cell_measurement_theta_max 27
_cell_measurement_temperature 150
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.26
_exptl_crystal_size_min 0.16
_exptl_crystal_density_diffrn 1.337
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 928
_exptl_absorpt_coefficient_mu 0.282
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(DENZO/SCALEPACK; Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min 0.81
_exptl_absorpt_correction_T_max 0.96
_diffrn_ambient_temperature 150
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Nonius KappaCCD'
_diffrn_measurement_device Area
_diffrn_measurement_method \w
_diffrn_reflns_number 9037
_diffrn_reflns_av_R_equivalents 0.026
_diffrn_reflns_theta_min 5.354
_diffrn_reflns_theta_max 27.489
_diffrn_reflns_theta_full 26.939
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -25
_diffrn_reflns_limit_l_max 25
_diffrn_standards_number 0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time .
_diffrn_standards_decay_% .
_reflns_number_total 4913
_reflns_number_gt 3769
_reflns_threshold_expression I>2.0\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0611
_refine_ls_R_factor_gt 0.0430
_refine_ls_wR_factor_all 0.1200
_refine_ls_wR_factor_gt 0.0974
_refine_ls_wR_factor_ref 0.1200
_refine_ls_goodness_of_fit_ref 0.9413
_refine_ls_number_reflns 4913
_refine_ls_number_parameters 253
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
18.1 26.7 12.7 3.26
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_refine_ls_shift/su_max 0.0007367
_refine_ls_shift/su_mean 0.0001563
_refine_diff_density_max 0.44
_refine_diff_density_min -0.45
_refine_ls_extinction_method None
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'COLLECT (Nonius, 2001)'
_computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution 'Structure transformed from solution to I'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
loop_
_atom_site_type_symbol
_atom_site_label
_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_disorder_assembly
_atom_site_disorder_group
S S1 0.76119(5) 0.38474(5) 0.36998(4) 0.0300 Uani 1.0000 . .
O O2 0.89308(15) 0.41318(17) 0.41507(11) 0.0364 Uani 1.0000 . .
O O3 0.66953(15) 0.42735(15) 0.26930(10) 0.0323 Uani 1.0000 . .
C C4 0.6878(3) 0.5516(2) 0.24470(16) 0.0367 Uani 1.0000 . .
C C5 0.6338(2) 0.6612(2) 0.26038(15) 0.0339 Uani 1.0000 . .
C C6 0.7163(2) 0.6973(2) 0.35921(14) 0.0264 Uani 1.0000 . .
C C7 0.7400(2) 0.6076(2) 0.41473(14) 0.0263 Uani 1.0000 . .
N N8 0.70607(18) 0.47484(18) 0.40600(12) 0.0290 Uani 1.0000 . .
C C9 0.8076(2) 0.5400(2) 0.49846(15) 0.0304 Uani 1.0000 . .
C C10 0.7686(2) 0.8320(2) 0.39004(15) 0.0287 Uani 1.0000 . .
C C11 0.8463(2) 0.8483(2) 0.49132(16) 0.0375 Uani 1.0000 . .
C C12 0.6527(3) 0.9245(2) 0.33738(19) 0.0422 Uani 1.0000 . .
C C13 0.8567(3) 0.8629(3) 0.37153(19) 0.0437 Uani 1.0000 . .
O O14 0.7270(2) 0.25681(15) 0.36795(13) 0.0432 Uani 1.0000 . .
S S101 0.57657(5) 0.76790(6) 0.52200(4) 0.0317 Uani 1.0000 . .
O O102 0.52818(18) 0.88029(16) 0.46823(13) 0.0406 Uani 1.0000 . .
O O103 0.56585(15) 0.65307(16) 0.46757(11) 0.0336 Uani 1.0000 . .
C C104 0.4504(2) 0.6417(2) 0.37043(15) 0.0337 Uani 1.0000 . .
C C105 0.3360(2) 0.5815(2) 0.35276(15) 0.0315 Uani 1.0000 . .
C C106 0.2709(2) 0.66518(19) 0.37506(13) 0.0242 Uani 1.0000 . .
C C107 0.3442(2) 0.7152(2) 0.45643(14) 0.0267 Uani 1.0000 . .
N N108 0.48021(18) 0.71538(19) 0.53769(12) 0.0306 Uani 1.0000 . .
C C109 0.3827(2) 0.8079(2) 0.52405(15) 0.0333 Uani 1.0000 . .
C C110 0.1261(2) 0.6922(2) 0.30314(14) 0.0272 Uani 1.0000 . .
C C113 0.1009(2) 0.7770(2) 0.23011(16) 0.0355 Uani 1.0000 . .
C C111 0.0776(2) 0.7607(2) 0.34358(16) 0.0366 Uani 1.0000 . .
C C112 0.0498(2) 0.5682(2) 0.25950(17) 0.0392 Uani 1.0000 . .
O O114 0.70583(17) 0.7655(2) 0.60715(12) 0.0490 Uani 1.0000 . .
H H41 0.6410 0.5462 0.1804 0.0451 Uiso 1.0000 . .
H H42 0.7822 0.5649 0.2814 0.0452 Uiso 1.0000 . .
H H52 0.6319 0.7348 0.2288 0.0405 Uiso 1.0000 . .
H H51 0.5439 0.6382 0.2338 0.0406 Uiso 1.0000 . .
H H92 0.8998 0.5196 0.5347 0.0363 Uiso 1.0000 . .
H H91 0.7820 0.5490 0.5337 0.0376 Uiso 1.0000 . .
H H111 0.8731 0.9371 0.5069 0.0578 Uiso 1.0000 . .
H H112 0.9214 0.7914 0.5257 0.0581 Uiso 1.0000 . .
H H113 0.7897 0.8276 0.5028 0.0580 Uiso 1.0000 . .
H H122 0.6884 1.0092 0.3558 0.0638 Uiso 1.0000 . .
H H121 0.6007 0.9142 0.2717 0.0643 Uiso 1.0000 . .
H H123 0.6009 0.9099 0.3535 0.0645 Uiso 1.0000 . .
H H132 0.8828 0.9509 0.3876 0.0671 Uiso 1.0000 . .
H H131 0.8083 0.8494 0.3067 0.0669 Uiso 1.0000 . .
H H133 0.9323 0.8090 0.4088 0.0673 Uiso 1.0000 . .
H H1041 0.4779 0.5873 0.3464 0.0414 Uiso 1.0000 . .
H H1042 0.4272 0.7275 0.3435 0.0409 Uiso 1.0000 . .
H H1052 0.2694 0.5622 0.2868 0.0398 Uiso 1.0000 . .
H H1051 0.3675 0.5021 0.3890 0.0398 Uiso 1.0000 . .
H H1092 0.3866 0.8973 0.5139 0.0425 Uiso 1.0000 . .
H H1091 0.3677 0.7953 0.5647 0.0421 Uiso 1.0000 . .
H H1131 0.0080 0.7924 0.1816 0.0526 Uiso 1.0000 . .
H H1132 0.1320 0.7354 0.2039 0.0533 Uiso 1.0000 . .
H H1133 0.1450 0.8590 0.2552 0.0526 Uiso 1.0000 . .
H H1112 -0.0160 0.7757 0.2959 0.0555 Uiso 1.0000 . .
H H1111 0.0953 0.7089 0.3922 0.0562 Uiso 1.0000 . .
H H1113 0.1204 0.8440 0.3685 0.0557 Uiso 1.0000 . .
H H1122 -0.0432 0.5882 0.2147 0.0602 Uiso 1.0000 . .
H H1121 0.0753 0.5233 0.2297 0.0604 Uiso 1.0000 . .
H H1123 0.0657 0.5134 0.3054 0.0600 Uiso 1.0000 . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0344(3) 0.0258(3) 0.0339(3) 0.0005(2) 0.0245(2) -0.0004(2)
O2 0.0295(8) 0.0442(10) 0.0366(8) 0.0026(7) 0.0226(7) -0.0043(7)
O3 0.0338(8) 0.0312(8) 0.0287(8) -0.0050(6) 0.0196(7) -0.0047(6)
C4 0.0477(13) 0.0368(12) 0.0275(11) -0.0023(10) 0.0259(11) -0.0002(9)
C5 0.0352(11) 0.0339(12) 0.0255(10) 0.0003(9) 0.0174(9) 0.0031(9)
C6 0.0259(10) 0.0280(10) 0.0271(10) 0.0025(8) 0.0185(9) 0.0022(8)
C7 0.0255(9) 0.0282(10) 0.0282(10) 0.0013(8) 0.0191(9) 0.0001(8)
N8 0.0317(9) 0.0281(9) 0.0323(9) 0.0014(7) 0.0235(8) 0.0015(7)
C9 0.0365(11) 0.0299(11) 0.0301(10) 0.0051(9) 0.0244(10) 0.0043(9)
C10 0.0294(10) 0.0260(10) 0.0345(11) 0.0013(8) 0.0229(9) 0.0029(8)
C11 0.0402(12) 0.0351(12) 0.0351(12) -0.0055(10) 0.0243(11) -0.0069(10)
C12 0.0413(13) 0.0300(12) 0.0523(15) 0.0042(10) 0.0301(12) 0.0063(11)
C13 0.0421(14) 0.0467(15) 0.0539(15) -0.0037(11) 0.0369(13) 0.0027(12)
O14 0.0624(12) 0.0229(8) 0.0595(12) -0.0032(8) 0.0470(11) -0.0015(7)
S101 0.0287(3) 0.0360(3) 0.0318(3) -0.0046(2) 0.0209(2) -0.0057(2)
O102 0.0512(10) 0.0306(9) 0.0519(10) -0.0060(7) 0.0395(9) -0.0037(8)
O103 0.0288(8) 0.0365(9) 0.0336(8) 0.0039(7) 0.0201(7) -0.0035(7)
C104 0.0307(11) 0.0400(12) 0.0316(11) 0.0011(9) 0.0214(10) -0.0073(9)
C105 0.0312(11) 0.0285(11) 0.0322(11) 0.0022(9) 0.0200(10) -0.0043(9)
C106 0.0280(10) 0.0218(9) 0.0255(9) -0.0009(8) 0.0190(8) 0.0008(7)
C107 0.0270(10) 0.0277(10) 0.0279(10) 0.0007(8) 0.0194(9) 0.0014(8)
N108 0.0279(9) 0.0381(10) 0.0254(8) 0.0011(8) 0.0177(8) 0.0005(8)
C109 0.0326(11) 0.0410(13) 0.0298(11) -0.0034(9) 0.0224(10) -0.0089(9)
C110 0.0267(10) 0.0287(10) 0.0275(10) 0.0006(8) 0.0187(9) 0.0042(8)
C113 0.0371(12) 0.0375(12) 0.0331(11) 0.0044(10) 0.0240(10) 0.0084(10)
C111 0.0341(12) 0.0457(14) 0.0366(12) 0.0093(10) 0.0264(11) 0.0061(10)
C112 0.0340(12) 0.0365(13) 0.0407(13) -0.0070(10) 0.0223(11) -0.0011(10)
O114 0.0285(9) 0.0710(14) 0.0377(9) -0.0099(8) 0.0181(8) -0.0121(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O2 . . 1.4278(17) no
S1 O3 . . 1.5573(16) no
S1 N8 . . 1.6527(18) no
S1 O14 . . 1.4189(17) no
O3 C4 . . 1.476(3) no
C4 C5 . . 1.517(3) no
C4 H41 . . 0.976 no
C4 H42 . . 0.993 no
C5 C6 . . 1.521(3) no
C5 H52 . . 0.988 no
C5 H51 . . 1.003 no
C6 C7 . . 1.318(3) no
C6 C10 . . 1.522(3) no
C7 N8 . . 1.447(3) no
C7 C9 . . 1.440(3) no
N8 C9 . . 1.540(3) no
C9 H92 . . 0.982 no
C9 H91 . . 0.981 no
C10 C11 . . 1.533(3) no
C10 C12 . . 1.540(3) no
C10 C13 . . 1.529(3) no
C11 H111 . . 0.977 no
C11 H112 . . 0.978 no
C11 H113 . . 0.977 no
C12 H122 . . 0.964 no
C12 H121 . . 0.989 no
C12 H123 . . 0.976 no
C13 H132 . . 0.967 no
C13 H131 . . 0.989 no
C13 H133 . . 0.964 no
S101 O103 . . 1.5628(16) no
S101 N108 . . 1.6571(19) no
S101 O114 . . 1.4204(18) no
S101 O102 . . 1.4262(19) no
O103 C104 . . 1.474(3) no
C104 C105 . . 1.514(3) no
C104 H1041 . . 0.972 no
C104 H1042 . . 0.988 no
C105 C106 . . 1.525(3) no
C105 H1052 . . 0.998 no
C105 H1051 . . 0.994 no
C106 C107 . . 1.316(3) no
C106 C110 . . 1.519(3) no
C107 N108 . . 1.445(3) no
C107 C109 . . 1.445(3) no
N108 C109 . . 1.535(3) no
C109 H1092 . . 0.972 no
C109 H1091 . . 0.972 no
C110 C113 . . 1.535(3) no
C110 C111 . . 1.532(3) no
C110 C112 . . 1.532(3) no
C113 H1131 . . 0.975 no
C113 H1132 . . 0.975 no
C113 H1133 . . 0.979 no
C111 H1112 . . 0.979 no
C111 H1111 . . 0.989 no
C111 H1113 . . 0.986 no
C112 H1122 . . 0.980 no
C112 H1121 . . 0.992 no
C112 H1123 . . 0.973 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O3 . . . 110.26(10) no
O2 S1 N8 . . . 112.07(10) no
O3 S1 N8 . . . 100.28(9) no
O2 S1 O14 . . . 118.64(11) no
O3 S1 O14 . . . 105.53(11) no
N8 S1 O14 . . . 108.31(10) no
S1 O3 C4 . . . 120.62(14) no
O3 C4 C5 . . . 112.78(19) no
O3 C4 H41 . . . 105.9 no
C5 C4 H41 . . . 109.3 no
O3 C4 H42 . . . 108.3 no
C5 C4 H42 . . . 109.3 no
H41 C4 H42 . . . 111.3 no
C4 C5 C6 . . . 114.16(19) no
C4 C5 H52 . . . 105.7 no
C6 C5 H52 . . . 107.8 no
C4 C5 H51 . . . 108.5 no
C6 C5 H51 . . . 109.6 no
H52 C5 H51 . . . 111.1 no
C5 C6 C7 . . . 117.2(2) no
C5 C6 C10 . . . 119.81(18) no
C7 C6 C10 . . . 123.01(19) no
C6 C7 N8 . . . 135.4(2) no
C6 C7 C9 . . . 158.4(2) no
N8 C7 C9 . . . 64.49(15) no
C7 N8 S1 . . . 113.52(14) no
C7 N8 C9 . . . 57.53(13) no
S1 N8 C9 . . . 117.21(14) no
N8 C9 C7 . . . 57.98(13) no
N8 C9 H92 . . . 118.6 no
C7 C9 H92 . . . 118.5 no
N8 C9 H91 . . . 114.9 no
C7 C9 H91 . . . 121.0 no
H92 C9 H91 . . . 114.3 no
C6 C10 C11 . . . 111.09(18) no
C6 C10 C12 . . . 108.48(18) no
C11 C10 C12 . . . 108.6(2) no
C6 C10 C13 . . . 110.01(19) no
C11 C10 C13 . . . 108.9(2) no
C12 C10 C13 . . . 109.8(2) no
C10 C11 H111 . . . 107.8 no
C10 C11 H112 . . . 109.5 no
H111 C11 H112 . . . 111.3 no
C10 C11 H113 . . . 108.5 no
H111 C11 H113 . . . 109.5 no
H112 C11 H113 . . . 110.2 no
C10 C12 H122 . . . 106.9 no
C10 C12 H121 . . . 109.6 no
H122 C12 H121 . . . 109.8 no
C10 C12 H123 . . . 109.7 no
H122 C12 H123 . . . 108.9 no
H121 C12 H123 . . . 111.9 no
C10 C13 H132 . . . 107.8 no
C10 C13 H131 . . . 109.4 no
H132 C13 H131 . . . 110.2 no
C10 C13 H133 . . . 108.7 no
H132 C13 H133 . . . 109.7 no
H131 C13 H133 . . . 111.0 no
O103 S101 N108 . . . 99.14(10) no
O103 S101 O114 . . . 105.83(11) no
N108 S101 O114 . . . 107.45(11) no
O103 S101 O102 . . . 109.99(10) no
N108 S101 O102 . . . 112.66(10) no
O114 S101 O102 . . . 119.62(12) no
S101 O103 C104 . . . 119.29(14) no
O103 C104 C105 . . . 112.71(18) no
O103 C104 H1041 . . . 104.8 no
C105 C104 H1041 . . . 109.5 no
O103 C104 H1042 . . . 108.2 no
C105 C104 H1042 . . . 110.3 no
H1041 C104 H1042 . . . 111.3 no
C104 C105 C106 . . . 115.00(18) no
C104 C105 H1052 . . . 107.0 no
C106 C105 H1052 . . . 107.1 no
C104 C105 H1051 . . . 107.5 no
C106 C105 H1051 . . . 109.4 no
H1052 C105 H1051 . . . 110.8 no
C105 C106 C107 . . . 118.06(19) no
C105 C106 C110 . . . 119.92(18) no
C107 C106 C110 . . . 121.99(19) no
C106 C107 N108 . . . 137.1(2) no
C106 C107 C109 . . . 156.5(2) no
N108 C107 C109 . . . 64.17(15) no
C107 N108 S101 . . . 113.62(14) no
C107 N108 C109 . . . 57.94(13) no
S101 N108 C109 . . . 118.68(15) no
N108 C109 C107 . . . 57.89(13) no
N108 C109 H1092 . . . 119.1 no
C107 C109 H1092 . . . 119.8 no
N108 C109 H1091 . . . 114.9 no
C107 C109 H1091 . . . 122.2 no
H1092 C109 H1091 . . . 112.3 no
C106 C110 C113 . . . 108.76(17) no
C106 C110 C111 . . . 111.08(18) no
C113 C110 C111 . . . 108.86(18) no
C106 C110 C112 . . . 110.47(18) no
C113 C110 C112 . . . 108.97(19) no
C111 C110 C112 . . . 108.66(19) no
C110 C113 H1131 . . . 110.4 no
C110 C113 H1132 . . . 110.1 no
H1131 C113 H1132 . . . 107.9 no
C110 C113 H1133 . . . 111.2 no
H1131 C113 H1133 . . . 108.5 no
H1132 C113 H1133 . . . 108.7 no
C110 C111 H1112 . . . 109.2 no
C110 C111 H1111 . . . 110.3 no
H1112 C111 H1111 . . . 109.7 no
C110 C111 H1113 . . . 110.8 no
H1112 C111 H1113 . . . 107.7 no
H1111 C111 H1113 . . . 109.1 no
C110 C112 H1122 . . . 108.8 no
C110 C112 H1121 . . . 111.0 no
H1122 C112 H1121 . . . 109.6 no
C110 C112 H1123 . . . 109.6 no
H1122 C112 H1123 . . . 108.4 no
H1121 C112 H1123 . . . 109.4 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C9 H92 O2 . . 2_766 0.98 2.43 3.294(4) 147 no
C9 H91 O103 . . . 0.98 2.57 3.203(4) 122 no
C109 H1092 O102 . . 2_676 0.97 2.54 3.473(4) 162 no
C109 H1091 O14 . . 2_666 0.97 2.49 3.433(4) 165 no