# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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. 
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#  fide research purposes only. It may contain copyright material 
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data_TBAsalt
_database_code_depnum_ccdc_archive 'CCDC 918967'
_chemical_name_common            'n-butylammoniun salt of tolbutamide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H12 N +, C12 H17 N2 O3 S -'
_chemical_formula_sum            'C16 H29 N3 O3 S'
_chemical_formula_weight         343.48
_exptl_crystal_preparation       
;
Microwave treatment of hot water-tolbutamide suspension
;
_chemical_compound_source        
;
Starting reagent was purchased from SIGMA
;
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'
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'
N N 0.0061 0.0033 '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/n'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
_cell_length_a                   13.5031(6)
_cell_length_b                   11.2985(5)
_cell_length_c                   25.4543(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.694(4)
_cell_angle_gamma                90.00
_cell_volume                     3838.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4754
_cell_measurement_theta_min      3.0187
_cell_measurement_theta_max      29.2275
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1488
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction KM4 CCD'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measurement_method       '\w scans'
_diffrn_reflns_number            18001
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0826
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         26.37
_reflns_number_total             7821
_reflns_number_gt                5534
_reflns_threshold_expression     >2sigma(I)
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  SHELXL-97
_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^)+(0.0476P)^2^+4.1860P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7821
_refine_ls_number_parameters     453
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1506
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.055
_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
S11 S 0.79105(5) 0.44025(7) 0.30819(3) 0.01746(18) Uani 1 1 d . . .
C11 C 0.6175(3) 0.3677(4) 0.51262(14) 0.0454(11) Uani 1 1 d . . .
H11A H 0.6052 0.2835 0.5182 0.068 Uiso 1 1 calc R . .
H11B H 0.5545 0.4116 0.5107 0.068 Uiso 1 1 calc R . .
H11C H 0.6657 0.3978 0.5423 0.068 Uiso 1 1 calc R . .
C12 C 0.6595(2) 0.3833(4) 0.46119(14) 0.0340(9) Uani 1 1 d . . .
C13 C 0.6816(3) 0.4948(4) 0.44467(15) 0.0454(10) Uani 1 1 d . . .
H13 H 0.6700 0.5611 0.4659 0.055 Uiso 1 1 calc R . .
C14 C 0.7203(3) 0.5130(3) 0.39790(15) 0.0415(10) Uani 1 1 d . . .
H14 H 0.7350 0.5909 0.3872 0.050 Uiso 1 1 calc R . .
C15 C 0.7375(2) 0.4164(3) 0.36686(12) 0.0212(7) Uani 1 1 d . . .
C16 C 0.7154(2) 0.3034(3) 0.38251(13) 0.0261(8) Uani 1 1 d . . .
H16 H 0.7265 0.2370 0.3613 0.031 Uiso 1 1 calc R . .
C17 C 0.6766(2) 0.2881(3) 0.42972(14) 0.0317(8) Uani 1 1 d . . .
H17 H 0.6617 0.2105 0.4405 0.038 Uiso 1 1 calc R . .
C18 C 0.6330(2) 0.5360(3) 0.26042(11) 0.0146(6) Uani 1 1 d . . .
C19 C 0.4805(2) 0.6406(3) 0.22144(13) 0.0226(7) Uani 1 1 d . . .
H19A H 0.4505 0.6604 0.2535 0.027 Uiso 1 1 calc R . .
H19B H 0.4533 0.5631 0.2080 0.027 Uiso 1 1 calc R . .
C50 C 0.4515(2) 0.7342(3) 0.17939(12) 0.0227(7) Uani 1 1 d . . .
H50A H 0.4797 0.8110 0.1930 0.027 Uiso 1 1 calc R . .
H50B H 0.3776 0.7419 0.1733 0.027 Uiso 1 1 calc R . .
C51 C 0.4864(2) 0.7092(3) 0.12656(13) 0.0257(7) Uani 1 1 d . . .
H51A H 0.5605 0.7120 0.1316 0.031 Uiso 1 1 calc R . .
H51B H 0.4612 0.7726 0.1012 0.031 Uiso 1 1 calc R . .
C52 C 0.4518(3) 0.5900(3) 0.10249(15) 0.0397(9) Uani 1 1 d . . .
H52A H 0.4863 0.5263 0.1241 0.060 Uiso 1 1 calc R . .
H52B H 0.4676 0.5850 0.0662 0.060 Uiso 1 1 calc R . .
H52C H 0.3793 0.5821 0.1017 0.060 Uiso 1 1 calc R . .
O11 O 0.89284(14) 0.47882(18) 0.32498(8) 0.0230(5) Uani 1 1 d . . .
O12 O 0.78066(14) 0.32953(18) 0.27904(8) 0.0219(5) Uani 1 1 d . . .
O13 O 0.58332(14) 0.44478(17) 0.26676(8) 0.0175(5) Uani 1 1 d . . .
N11 N 0.73421(17) 0.5486(2) 0.27736(10) 0.0163(5) Uani 1 1 d . . .
N12 N 0.58887(18) 0.6315(2) 0.23577(10) 0.0186(6) Uani 1 1 d . . .
H12N H 0.626(2) 0.690(3) 0.2327(13) 0.022(9) Uiso 1 1 d . . .
S21 S 0.23462(5) 0.15788(7) 0.18903(3) 0.01563(18) Uani 1 1 d . . .
C21 C 0.4422(3) 0.1841(4) -0.00574(14) 0.0384(9) Uani 1 1 d . . .
H21A H 0.5118 0.1568 0.0017 0.058 Uiso 1 1 calc R . .
H21B H 0.4405 0.2656 -0.0190 0.058 Uiso 1 1 calc R . .
H21C H 0.4043 0.1328 -0.0326 0.058 Uiso 1 1 calc R . .
C22 C 0.3961(2) 0.1795(3) 0.04448(12) 0.0256(8) Uani 1 1 d . . .
C23 C 0.3488(2) 0.2776(3) 0.06213(12) 0.0260(8) Uani 1 1 d . . .
H23 H 0.3472 0.3493 0.0426 0.031 Uiso 1 1 calc R . .
C24 C 0.3036(2) 0.2738(3) 0.10761(12) 0.0218(7) Uani 1 1 d . . .
H24 H 0.2715 0.3419 0.1190 0.026 Uiso 1 1 calc R . .
C25 C 0.3061(2) 0.1689(3) 0.13616(11) 0.0158(6) Uani 1 1 d . . .
C26 C 0.3553(2) 0.0707(3) 0.12002(12) 0.0217(7) Uani 1 1 d . . .
H26 H 0.3585 -0.0005 0.1401 0.026 Uiso 1 1 calc R . .
C27 C 0.3996(2) 0.0770(3) 0.07470(13) 0.0274(8) Uani 1 1 d . . .
H27 H 0.4334 0.0095 0.0639 0.033 Uiso 1 1 calc R . .
C28 C 0.3740(2) 0.0586(3) 0.25082(11) 0.0152(6) Uani 1 1 d . . .
N22 N 0.4067(2) -0.0413(2) 0.27643(11) 0.0213(6) Uani 1 1 d . A .
C29 C 0.5090(2) -0.0577(3) 0.30252(15) 0.0367(9) Uani 1 1 d D . .
H29A H 0.5545 -0.0238 0.2794 0.044 Uiso 0.560(6) 1 calc PR A 1
H29B H 0.5226 -0.1437 0.3053 0.044 Uiso 0.560(6) 1 calc PR A 1
H29C H 0.5469 0.0173 0.3025 0.044 Uiso 0.440(6) 1 d PR A 2
H29D H 0.5430 -0.1187 0.2838 0.044 Uiso 0.440(6) 1 d PR A 2
C60A C 0.5344(5) -0.0058(7) 0.3554(3) 0.044(2) Uiso 0.560(6) 1 d PD A 1
H60A H 0.5026 0.0728 0.3568 0.053 Uiso 0.560(6) 1 calc PR A 1
H60B H 0.6079 0.0036 0.3647 0.053 Uiso 0.560(6) 1 calc PR A 1
C61A C 0.4939(8) -0.0935(8) 0.3949(4) 0.084(3) Uiso 0.560(6) 1 d PD A 1
H61A H 0.5010 -0.0567 0.4306 0.101 Uiso 0.560(6) 1 calc PR A 1
H61B H 0.4216 -0.1078 0.3829 0.101 Uiso 0.560(6) 1 calc PR A 1
C62A C 0.5494(8) -0.2124(9) 0.3990(4) 0.097(4) Uiso 0.560(6) 1 d PD A 1
H62A H 0.5356 -0.2538 0.3648 0.146 Uiso 0.560(6) 1 calc PR A 1
H62B H 0.5264 -0.2609 0.4267 0.146 Uiso 0.560(6) 1 calc PR A 1
H62C H 0.6215 -0.1984 0.4080 0.146 Uiso 0.560(6) 1 calc PR A 1
C60B C 0.5033(9) -0.0998(10) 0.3641(4) 0.073(4) Uiso 0.440(6) 1 d PD A 2
H60C H 0.4601 -0.1708 0.3633 0.088 Uiso 0.440(6) 1 calc PR A 2
H60D H 0.5712 -0.1221 0.3816 0.088 Uiso 0.440(6) 1 calc PR A 2
C61B C 0.4629(8) -0.0057(10) 0.3962(3) 0.056(3) Uiso 0.440(6) 1 d PD A 2
H61C H 0.3948 0.0142 0.3781 0.067 Uiso 0.440(6) 1 calc PR A 2
H61D H 0.5048 0.0657 0.3944 0.067 Uiso 0.440(6) 1 calc PR A 2
C62B C 0.4556(8) -0.0278(10) 0.4548(4) 0.064(3) Uiso 0.440(6) 1 d PD A 2
H62D H 0.4064 -0.0904 0.4576 0.095 Uiso 0.440(6) 1 calc PR A 2
H62E H 0.4344 0.0451 0.4708 0.095 Uiso 0.440(6) 1 calc PR A 2
H62F H 0.5212 -0.0522 0.4735 0.095 Uiso 0.440(6) 1 calc PR A 2
O21 O 0.13455(14) 0.12538(19) 0.16478(8) 0.0209(5) Uani 1 1 d . . .
O22 O 0.24185(14) 0.27265(18) 0.21519(8) 0.0198(5) Uani 1 1 d . . .
O23 O 0.42945(14) 0.14737(18) 0.25024(8) 0.0198(5) Uani 1 1 d . . .
N21 N 0.27638(17) 0.0503(2) 0.22535(9) 0.0163(5) Uani 1 1 d . . .
H22N H 0.368(2) -0.094(3) 0.2770(12) 0.016(9) Uiso 1 1 d . . .
N31 N 0.6071(2) 0.2241(3) 0.21761(11) 0.0181(6) Uani 1 1 d . . .
C31 C 0.5828(2) 0.2579(3) 0.16091(12) 0.0215(7) Uani 1 1 d . . .
H31D H 0.5163 0.2967 0.1549 0.026 Uiso 1 1 calc R . .
H31E H 0.5787 0.1856 0.1387 0.026 Uiso 1 1 calc R . .
C32 C 0.6601(2) 0.3412(3) 0.14370(13) 0.0248(7) Uani 1 1 d . . .
H32A H 0.7280 0.3077 0.1541 0.030 Uiso 1 1 calc R . .
H32B H 0.6573 0.4184 0.1618 0.030 Uiso 1 1 calc R . .
C33 C 0.6401(3) 0.3595(3) 0.08327(13) 0.0305(8) Uani 1 1 d . . .
H33A H 0.6590 0.2864 0.0657 0.037 Uiso 1 1 calc R . .
H33B H 0.5674 0.3720 0.0722 0.037 Uiso 1 1 calc R . .
C34 C 0.6964(3) 0.4631(4) 0.06407(16) 0.0463(10) Uani 1 1 d . . .
H34A H 0.6789 0.5358 0.0815 0.069 Uiso 1 1 calc R . .
H34B H 0.6781 0.4713 0.0255 0.069 Uiso 1 1 calc R . .
H34C H 0.7687 0.4491 0.0728 0.069 Uiso 1 1 calc R . .
H31A H 0.553(3) 0.184(3) 0.2284(14) 0.035(10) Uiso 1 1 d . . .
H31B H 0.658(3) 0.177(3) 0.2232(12) 0.021(9) Uiso 1 1 d . . .
H31C H 0.620(3) 0.290(4) 0.2400(16) 0.052(12) Uiso 1 1 d . . .
N41 N 0.3972(2) 0.3827(3) 0.28775(10) 0.0179(6) Uani 1 1 d . . .
C41 C 0.4292(2) 0.3559(3) 0.34503(12) 0.0206(7) Uani 1 1 d . . .
H41D H 0.4514 0.4298 0.3641 0.025 Uiso 1 1 calc R . .
H41E H 0.4869 0.3008 0.3488 0.025 Uiso 1 1 calc R . .
C42 C 0.3457(2) 0.3012(3) 0.36981(13) 0.0319(8) Uani 1 1 d . . .
H42A H 0.3283 0.2231 0.3533 0.038 Uiso 1 1 calc R . .
H42B H 0.2856 0.3523 0.3630 0.038 Uiso 1 1 calc R . .
C43 C 0.3765(3) 0.2860(4) 0.42941(15) 0.0523(12) Uani 1 1 d . . .
H43A H 0.3931 0.3644 0.4457 0.063 Uiso 1 1 calc R . .
H43B H 0.4375 0.2363 0.4360 0.063 Uiso 1 1 calc R . .
C44 C 0.2945(4) 0.2289(6) 0.45581(18) 0.087(2) Uani 1 1 d . . .
H44A H 0.2335 0.2769 0.4488 0.130 Uiso 1 1 calc R . .
H44B H 0.3166 0.2239 0.4942 0.130 Uiso 1 1 calc R . .
H44C H 0.2807 0.1492 0.4414 0.130 Uiso 1 1 calc R . .
H41A H 0.345(3) 0.432(3) 0.2831(13) 0.026(9) Uiso 1 1 d . . .
H41B H 0.449(3) 0.417(3) 0.2745(14) 0.036(10) Uiso 1 1 d . . .
H41C H 0.382(3) 0.312(4) 0.2682(15) 0.042(11) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S11 0.0152(3) 0.0136(4) 0.0229(4) -0.0012(3) 0.0007(3) 0.0007(3)
C11 0.0315(19) 0.074(3) 0.030(2) 0.018(2) 0.0032(16) 0.005(2)
C12 0.0264(17) 0.051(2) 0.0227(19) 0.0135(18) -0.0014(14) 0.0012(18)
C13 0.068(3) 0.040(2) 0.032(2) -0.0023(19) 0.0181(19) 0.006(2)
C14 0.068(3) 0.026(2) 0.034(2) -0.0016(17) 0.0168(19) -0.003(2)
C15 0.0219(15) 0.0188(16) 0.0215(17) 0.0029(13) -0.0020(12) 0.0020(14)
C16 0.0224(16) 0.0229(17) 0.0311(19) 0.0069(15) -0.0016(14) 0.0037(15)
C17 0.0267(17) 0.033(2) 0.034(2) 0.0173(17) -0.0014(15) -0.0027(16)
C18 0.0142(14) 0.0164(15) 0.0142(15) -0.0046(12) 0.0050(11) -0.0007(13)
C19 0.0137(14) 0.0289(18) 0.0252(18) 0.0048(15) 0.0028(12) -0.0029(14)
C50 0.0167(15) 0.0227(17) 0.0286(18) 0.0031(14) 0.0030(13) 0.0002(14)
C51 0.0290(17) 0.0234(17) 0.0249(18) 0.0041(15) 0.0047(14) 0.0025(15)
C52 0.048(2) 0.037(2) 0.033(2) -0.0039(18) 0.0005(17) 0.0045(19)
O11 0.0176(10) 0.0188(11) 0.0308(13) -0.0001(10) -0.0025(9) 0.0008(10)
O12 0.0197(10) 0.0169(11) 0.0282(13) -0.0056(10) 0.0003(9) 0.0023(9)
O13 0.0146(10) 0.0128(10) 0.0258(12) 0.0002(9) 0.0053(8) -0.0018(9)
N11 0.0147(11) 0.0118(12) 0.0219(14) 0.0016(11) 0.0011(10) 0.0001(11)
N12 0.0132(12) 0.0163(14) 0.0257(15) 0.0055(12) 0.0007(10) -0.0035(12)
S21 0.0145(3) 0.0170(4) 0.0156(4) -0.0005(3) 0.0030(3) -0.0008(3)
C21 0.038(2) 0.054(3) 0.026(2) 0.0000(18) 0.0135(16) -0.0087(19)
C22 0.0231(16) 0.038(2) 0.0163(17) -0.0005(15) 0.0051(13) -0.0080(16)
C23 0.0267(17) 0.0300(19) 0.0199(17) 0.0077(15) -0.0006(13) -0.0067(16)
C24 0.0189(15) 0.0251(17) 0.0209(17) 0.0021(14) 0.0014(12) 0.0006(14)
C25 0.0156(14) 0.0165(15) 0.0144(15) -0.0012(12) -0.0007(11) -0.0026(13)
C26 0.0236(16) 0.0224(17) 0.0195(17) 0.0011(14) 0.0042(13) -0.0027(14)
C27 0.0278(17) 0.0301(19) 0.0255(18) -0.0061(15) 0.0077(14) 0.0018(16)
C28 0.0153(14) 0.0171(15) 0.0147(15) -0.0019(13) 0.0071(11) -0.0003(13)
N22 0.0179(13) 0.0164(14) 0.0281(16) 0.0023(12) -0.0011(11) -0.0036(13)
C29 0.0223(17) 0.0276(19) 0.056(3) 0.0029(18) -0.0088(16) 0.0020(16)
O21 0.0159(10) 0.0254(12) 0.0210(12) 0.0007(10) 0.0019(8) -0.0004(9)
O22 0.0187(10) 0.0186(11) 0.0224(12) -0.0023(9) 0.0045(9) 0.0031(9)
O23 0.0157(10) 0.0151(11) 0.0289(13) 0.0002(9) 0.0049(9) -0.0017(9)
N21 0.0179(12) 0.0152(13) 0.0160(13) -0.0006(11) 0.0029(10) -0.0036(11)
N31 0.0115(13) 0.0158(14) 0.0266(16) -0.0006(12) 0.0019(11) 0.0003(12)
C31 0.0222(15) 0.0172(16) 0.0231(17) 0.0014(14) -0.0034(13) 0.0009(14)
C32 0.0244(16) 0.0228(17) 0.0277(18) 0.0000(15) 0.0057(13) 0.0006(15)
C33 0.0392(19) 0.0247(18) 0.0283(19) 0.0011(15) 0.0074(15) 0.0044(16)
C34 0.054(2) 0.047(3) 0.042(2) 0.014(2) 0.0186(19) 0.003(2)
N41 0.0131(13) 0.0178(14) 0.0231(15) -0.0008(12) 0.0032(11) 0.0008(13)
C41 0.0163(14) 0.0230(17) 0.0212(17) 0.0021(14) -0.0015(12) -0.0018(14)
C42 0.0227(16) 0.047(2) 0.0255(19) 0.0037(17) 0.0018(14) -0.0123(17)
C43 0.050(2) 0.076(3) 0.029(2) 0.011(2) 0.0021(18) -0.030(2)
C44 0.085(4) 0.144(6) 0.031(3) 0.009(3) 0.012(2) -0.060(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
S11 O11 1.444(2) . ?
S11 O12 1.450(2) . ?
S11 N11 1.588(2) . ?
S11 C15 1.776(3) . ?
C11 C12 1.514(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.375(5) . ?
C12 C17 1.382(5) . ?
C13 C14 1.386(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(4) . ?
C16 C17 1.392(5) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 O13 1.253(3) . ?
C18 N12 1.342(4) . ?
C18 N11 1.377(3) . ?
C19 N12 1.457(4) . ?
C19 C50 1.513(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C50 C51 1.517(4) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 C52 1.523(5) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
N12 H12N 0.84(3) . ?
S21 O21 1.446(2) . ?
S21 O22 1.454(2) . ?
S21 N21 1.578(2) . ?
S21 C25 1.775(3) . ?
C21 C22 1.505(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C27 1.387(5) . ?
C22 C23 1.388(5) . ?
C23 C24 1.388(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.388(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.387(4) . ?
C26 C27 1.380(4) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 O23 1.253(3) . ?
C28 N22 1.344(4) . ?
C28 N21 1.382(4) . ?
N22 C29 1.452(4) . ?
N22 H22N 0.80(3) . ?
C29 C60A 1.461(7) . ?
C29 C60B 1.652(11) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 H29C 0.9900 . ?
C29 H29D 0.9900 . ?
C60A C61A 1.568(10) . ?
C60A H29C 1.4067 . ?
C60A H60A 0.9900 . ?
C60A H60B 0.9900 . ?
C61A C62A 1.534(10) . ?
C61A H61A 0.9900 . ?
C61A H61B 0.9900 . ?
C62A H62A 0.9800 . ?
C62A H62B 0.9800 . ?
C62A H62C 0.9800 . ?
C60B C61B 1.492(11) . ?
C60B H60C 0.9900 . ?
C60B H60D 0.9900 . ?
C61B C62B 1.531(9) . ?
C61B H61C 0.9900 . ?
C61B H61D 0.9900 . ?
C62B H62D 0.9800 . ?
C62B H62E 0.9800 . ?
C62B H62F 0.9800 . ?
N31 C31 1.481(4) . ?
N31 H31A 0.93(4) . ?
N31 H31B 0.87(3) . ?
N31 H31C 0.94(4) . ?
C31 C32 1.518(4) . ?
C31 H31D 0.9900 . ?
C31 H31E 0.9900 . ?
C32 C33 1.535(4) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.517(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
N41 C41 1.488(4) . ?
N41 H41A 0.89(4) . ?
N41 H41B 0.91(4) . ?
N41 H41C 0.95(4) . ?
C41 C42 1.505(4) . ?
C41 H41D 0.9900 . ?
C41 H41E 0.9900 . ?
C42 C43 1.521(5) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C43 C44 1.522(6) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
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
O11 S11 O12 115.22(13) . . ?
O11 S11 N11 106.32(12) . . ?
O12 S11 N11 114.21(13) . . ?
O11 S11 C15 106.70(14) . . ?
O12 S11 C15 106.22(14) . . ?
N11 S11 C15 107.72(13) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 118.2(3) . . ?
C13 C12 C11 119.9(4) . . ?
C17 C12 C11 121.9(4) . . ?
C12 C13 C14 121.7(4) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C13 C14 C15 119.3(3) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 S11 121.0(3) . . ?
C14 C15 S11 119.0(3) . . ?
C15 C16 C17 119.2(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C12 C17 C16 121.4(3) . . ?
C12 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
O13 C18 N12 120.9(2) . . ?
O13 C18 N11 124.8(3) . . ?
N12 C18 N11 114.4(2) . . ?
N12 C19 C50 111.7(2) . . ?
N12 C19 H19A 109.3 . . ?
C50 C19 H19A 109.3 . . ?
N12 C19 H19B 109.3 . . ?
C50 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C19 C50 C51 114.5(3) . . ?
C19 C50 H50A 108.6 . . ?
C51 C50 H50A 108.6 . . ?
C19 C50 H50B 108.6 . . ?
C51 C50 H50B 108.6 . . ?
H50A C50 H50B 107.6 . . ?
C50 C51 C52 113.8(3) . . ?
C50 C51 H51A 108.8 . . ?
C52 C51 H51A 108.8 . . ?
C50 C51 H51B 108.8 . . ?
C52 C51 H51B 108.8 . . ?
H51A C51 H51B 107.7 . . ?
C51 C52 H52A 109.5 . . ?
C51 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C51 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C18 N11 S11 117.2(2) . . ?
C18 N12 C19 122.2(3) . . ?
C18 N12 H12N 117(2) . . ?
C19 N12 H12N 120(2) . . ?
O21 S21 O22 114.57(12) . . ?
O21 S21 N21 106.42(12) . . ?
O22 S21 N21 115.14(13) . . ?
O21 S21 C25 105.92(13) . . ?
O22 S21 C25 106.15(13) . . ?
N21 S21 C25 108.13(13) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 117.8(3) . . ?
C27 C22 C21 121.1(3) . . ?
C23 C22 C21 121.2(3) . . ?
C22 C23 C24 121.8(3) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C25 C24 C23 118.9(3) . . ?
C25 C24 H24 120.5 . . ?
C23 C24 H24 120.5 . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 S21 120.5(2) . . ?
C24 C25 S21 118.9(2) . . ?
C27 C26 C25 119.6(3) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C22 121.6(3) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
O23 C28 N22 121.7(3) . . ?
O23 C28 N21 125.3(3) . . ?
N22 C28 N21 113.0(3) . . ?
C28 N22 C29 123.3(3) . . ?
C28 N22 H22N 118(2) . . ?
C29 N22 H22N 118(2) . . ?
N22 C29 C60A 116.4(4) . . ?
N22 C29 C60B 107.1(5) . . ?
C60A C29 C60B 43.8(5) . . ?
N22 C29 H29A 108.2 . . ?
C60A C29 H29A 108.2 . . ?
C60B C29 H29A 142.9 . . ?
N22 C29 H29B 108.2 . . ?
C60A C29 H29B 108.2 . . ?
C60B C29 H29B 71.5 . . ?
H29A C29 H29B 107.3 . . ?
N22 C29 H29C 110.3 . . ?
C60A C29 H29C 66.9 . . ?
C60B C29 H29C 110.2 . . ?
H29A C29 H29C 45.6 . . ?
H29B C29 H29C 138.6 . . ?
N22 C29 H29D 110.3 . . ?
C60A C29 H29D 131.5 . . ?
C60B C29 H29D 110.4 . . ?
H29A C29 H29D 66.9 . . ?
H29B C29 H29D 42.0 . . ?
H29C C29 H29D 108.6 . . ?
C29 C60A C61A 106.3(6) . . ?
C29 C60A H29C 40.3 . . ?
C61A C60A H29C 146.6 . . ?
C29 C60A H60A 110.5 . . ?
C61A C60A H60A 110.5 . . ?
H29C C60A H60A 89.0 . . ?
C29 C60A H60B 110.5 . . ?
C61A C60A H60B 110.5 . . ?
H29C C60A H60B 86.9 . . ?
H60A C60A H60B 108.7 . . ?
C62A C61A C60A 112.5(8) . . ?
C62A C61A H61A 109.1 . . ?
C60A C61A H61A 109.1 . . ?
C62A C61A H61B 109.1 . . ?
C60A C61A H61B 109.1 . . ?
H61A C61A H61B 107.8 . . ?
C61B C60B C29 112.8(7) . . ?
C61B C60B H60C 109.0 . . ?
C29 C60B H60C 109.0 . . ?
C61B C60B H60D 109.0 . . ?
C29 C60B H60D 109.0 . . ?
H60C C60B H60D 107.8 . . ?
C60B C61B C62B 120.0(9) . . ?
C60B C61B H61C 107.3 . . ?
C62B C61B H61C 107.3 . . ?
C60B C61B H61D 107.3 . . ?
C62B C61B H61D 107.3 . . ?
H61C C61B H61D 106.9 . . ?
C61B C62B H62D 109.5 . . ?
C61B C62B H62E 109.5 . . ?
H62D C62B H62E 109.5 . . ?
C61B C62B H62F 109.5 . . ?
H62D C62B H62F 109.5 . . ?
H62E C62B H62F 109.5 . . ?
C28 N21 S21 117.0(2) . . ?
C31 N31 H31A 110(2) . . ?
C31 N31 H31B 112(2) . . ?
H31A N31 H31B 107(3) . . ?
C31 N31 H31C 112(2) . . ?
H31A N31 H31C 107(3) . . ?
H31B N31 H31C 108(3) . . ?
N31 C31 C32 112.4(2) . . ?
N31 C31 H31D 109.1 . . ?
C32 C31 H31D 109.1 . . ?
N31 C31 H31E 109.1 . . ?
C32 C31 H31E 109.1 . . ?
H31D C31 H31E 107.9 . . ?
C31 C32 C33 110.4(3) . . ?
C31 C32 H32A 109.6 . . ?
C33 C32 H32A 109.6 . . ?
C31 C32 H32B 109.6 . . ?
C33 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
C34 C33 C32 113.9(3) . . ?
C34 C33 H33A 108.8 . . ?
C32 C33 H33A 108.8 . . ?
C34 C33 H33B 108.8 . . ?
C32 C33 H33B 108.8 . . ?
H33A C33 H33B 107.7 . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C41 N41 H41A 111(2) . . ?
C41 N41 H41B 109(2) . . ?
H41A N41 H41B 109(3) . . ?
C41 N41 H41C 110(2) . . ?
H41A N41 H41C 111(3) . . ?
H41B N41 H41C 106(3) . . ?
N41 C41 C42 111.7(2) . . ?
N41 C41 H41D 109.3 . . ?
C42 C41 H41D 109.3 . . ?
N41 C41 H41E 109.3 . . ?
C42 C41 H41E 109.3 . . ?
H41D C41 H41E 107.9 . . ?
C41 C42 C43 110.8(3) . . ?
C41 C42 H42A 109.5 . . ?
C43 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C43 C42 H42B 109.5 . . ?
H42A C42 H42B 108.1 . . ?
C42 C43 C44 112.4(3) . . ?
C42 C43 H43A 109.1 . . ?
C44 C43 H43A 109.1 . . ?
C42 C43 H43B 109.1 . . ?
C44 C43 H43B 109.1 . . ?
H43A C43 H43B 107.9 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 C12 C13 C14 -0.2(6) . . . . ?
C11 C12 C13 C14 179.9(4) . . . . ?
C12 C13 C14 C15 -0.1(6) . . . . ?
C13 C14 C15 C16 0.4(6) . . . . ?
C13 C14 C15 S11 -177.9(3) . . . . ?
O11 S11 C15 C16 -110.1(3) . . . . ?
O12 S11 C15 C16 13.3(3) . . . . ?
N11 S11 C15 C16 136.1(2) . . . . ?
O11 S11 C15 C14 68.1(3) . . . . ?
O12 S11 C15 C14 -168.5(3) . . . . ?
N11 S11 C15 C14 -45.7(3) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
S11 C15 C16 C17 177.8(2) . . . . ?
C13 C12 C17 C16 0.1(5) . . . . ?
C11 C12 C17 C16 -179.9(3) . . . . ?
C15 C16 C17 C12 0.2(5) . . . . ?
N12 C19 C50 C51 63.3(3) . . . . ?
C19 C50 C51 C52 55.7(4) . . . . ?
O13 C18 N11 S11 -1.3(4) . . . . ?
N12 C18 N11 S11 178.5(2) . . . . ?
O11 S11 N11 C18 -175.7(2) . . . . ?
O12 S11 N11 C18 56.1(2) . . . . ?
C15 S11 N11 C18 -61.6(2) . . . . ?
O13 C18 N12 C19 8.2(4) . . . . ?
N11 C18 N12 C19 -171.6(3) . . . . ?
C50 C19 N12 C18 -161.3(3) . . . . ?
C27 C22 C23 C24 -1.8(5) . . . . ?
C21 C22 C23 C24 178.3(3) . . . . ?
C22 C23 C24 C25 0.1(5) . . . . ?
C23 C24 C25 C26 1.6(4) . . . . ?
C23 C24 C25 S21 -171.8(2) . . . . ?
O21 S21 C25 C26 -89.3(3) . . . . ?
O22 S21 C25 C26 148.5(2) . . . . ?
N21 S21 C25 C26 24.4(3) . . . . ?
O21 S21 C25 C24 84.1(3) . . . . ?
O22 S21 C25 C24 -38.1(3) . . . . ?
N21 S21 C25 C24 -162.2(2) . . . . ?
C24 C25 C26 C27 -1.6(4) . . . . ?
S21 C25 C26 C27 171.7(2) . . . . ?
C25 C26 C27 C22 -0.2(5) . . . . ?
C23 C22 C27 C26 1.8(5) . . . . ?
C21 C22 C27 C26 -178.2(3) . . . . ?
O23 C28 N22 C29 -3.8(5) . . . . ?
N21 C28 N22 C29 174.9(3) . . . . ?
C28 N22 C29 C60A 80.8(5) . . . . ?
C28 N22 C29 C60B 127.1(5) . . . . ?
N22 C29 C60A C61A 79.9(6) . . . . ?
C60B C29 C60A C61A -7.6(7) . . . . ?
C29 C60A C61A C62A 66.6(10) . . . . ?
N22 C29 C60B C61B -66.2(9) . . . . ?
C60A C29 C60B C61B 44.4(8) . . . . ?
C29 C60B C61B C62B -178.0(8) . . . . ?
O23 C28 N21 S21 5.1(4) . . . . ?
N22 C28 N21 S21 -173.6(2) . . . . ?
O21 S21 N21 C28 176.8(2) . . . . ?
O22 S21 N21 C28 -55.1(2) . . . . ?
C25 S21 N21 C28 63.4(2) . . . . ?
N31 C31 C32 C33 171.9(3) . . . . ?
C31 C32 C33 C34 165.7(3) . . . . ?
N41 C41 C42 C43 -174.2(3) . . . . ?
C41 C42 C43 C44 -179.0(4) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N12 H12N O12 0.84(3) 2.06(3) 2.908(3) 176(3) 2_655
N22 H22N O22 0.80(3) 2.14(3) 2.936(3) 174(3) 2_545
N31 H31A O23 0.93(4) 1.88(4) 2.792(3) 164(3) .
N31 H31B O11 0.87(3) 2.60(3) 2.975(4) 107(2) 2_645
N31 H31B N11 0.87(3) 2.05(4) 2.908(4) 168(3) 2_645
N31 H31C O12 0.94(4) 2.29(4) 2.873(3) 120(3) .
N31 H31C O13 0.94(4) 1.97(4) 2.830(4) 152(3) .
N41 H41A O21 0.89(4) 2.55(3) 3.052(4) 116(2) 2
N41 H41A N21 0.89(4) 2.11(4) 2.993(4) 178(3) 2
N41 H41B O13 0.91(4) 1.88(4) 2.738(3) 157(3) .
N41 H41C O22 0.95(4) 2.20(4) 2.861(3) 126(3) .
N41 H41C O23 0.95(4) 2.04(4) 2.881(4) 147(3) .
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.068


data_TSAbeta
_database_code_depnum_ccdc_archive 'CCDC 918969'
_chemical_name_common            p-toluenesulfonamide
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H9 N O2 S'
_chemical_formula_sum            'C7 H9 N O2 S'
_chemical_formula_weight         171.21
_exptl_crystal_preparation       
;
Microwave treatment of hot water-tolbutamide suspension
;
_chemical_compound_source        
;
Starting reagent was purchased from SIGMA
;
_exptl_special_details           'polymorph \b'
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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
_cell_length_a                   5.1562(2)
_cell_length_b                   8.3250(4)
_cell_length_c                   9.8583(7)
_cell_angle_alpha                100.801(5)
_cell_angle_beta                 102.284(4)
_cell_angle_gamma                90.371(3)
_cell_volume                     405.68(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2033
_cell_measurement_theta_min      3.5910
_cell_measurement_theta_max      28.1743
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             180
_exptl_absorpt_coefficient_mu    0.346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.897
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction KM4 CCD'
_diffrn_detector_area_resol_mean 10.3457
_diffrn_measurement_method       '\w scans'
_diffrn_reflns_number            5004
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0503
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.60
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3302
_reflns_number_gt                2790
_reflns_threshold_expression     >2sigma(I)
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  SHELXL-97
_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^)+(0.0430P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(7)
_refine_ls_number_reflns         3302
_refine_ls_number_parameters     217
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.0972
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
S11 S 0.50674(11) 0.87303(7) 0.16975(7) 0.0359(3) Uani 1 1 d . . .
O11 O 0.6190(4) 0.7219(2) 0.1209(2) 0.0485(6) Uani 1 1 d . . .
O12 O 0.6229(4) 1.0202(2) 0.1469(2) 0.0442(6) Uani 1 1 d . . .
N11 N 0.2002(5) 0.8624(4) 0.0933(3) 0.0412(6) Uani 1 1 d . . .
C11 C 0.5313(6) 0.8919(3) 0.3532(3) 0.0377(7) Uani 1 1 d . . .
C12 C 0.7338(7) 0.8185(4) 0.4329(4) 0.0533(9) Uani 1 1 d . . .
H12A H 0.8506 0.7543 0.3889 0.064 Uiso 1 1 calc R . .
C13 C 0.7616(7) 0.8407(5) 0.5770(4) 0.0656(11) Uani 1 1 d . . .
H13 H 0.8969 0.7897 0.6292 0.079 Uiso 1 1 calc R . .
C14 C 0.5934(8) 0.9368(5) 0.6466(4) 0.0613(10) Uani 1 1 d . . .
C15 C 0.3937(8) 1.0098(5) 0.5654(4) 0.0590(9) Uani 1 1 d . . .
H15 H 0.2780 1.0746 0.6097 0.071 Uiso 1 1 calc R . .
C16 C 0.3612(7) 0.9891(4) 0.4206(4) 0.0488(8) Uani 1 1 d . . .
H16 H 0.2259 1.0401 0.3684 0.059 Uiso 1 1 calc R . .
C17 C 0.6282(13) 0.9622(7) 0.8042(5) 0.104(2) Uani 1 1 d . . .
H17A H 0.4570 0.9637 0.8280 0.156 Uiso 1 1 calc R . .
H17B H 0.7246 1.0645 0.8471 0.156 Uiso 1 1 calc R . .
H17C H 0.7253 0.8745 0.8383 0.156 Uiso 1 1 calc R . .
H11 H 0.110(6) 0.776(4) 0.098(3) 0.033(8) Uiso 1 1 d . . .
H12 H 0.122(6) 0.949(4) 0.108(3) 0.038(9) Uiso 1 1 d . . .
S21 S 0.02364(11) 0.38416(8) 0.20094(7) 0.0381(3) Uani 1 1 d . . .
O21 O 0.1419(4) 0.5311(3) 0.1794(2) 0.0507(6) Uani 1 1 d . . .
O22 O 0.1374(4) 0.2319(3) 0.1564(2) 0.0496(6) Uani 1 1 d . . .
N21 N -0.2817(5) 0.3703(4) 0.1188(3) 0.0418(7) Uani 1 1 d . . .
C21 C 0.0409(6) 0.4068(3) 0.3840(3) 0.0382(7) Uani 1 1 d . . .
C22 C 0.2420(7) 0.5037(4) 0.4782(4) 0.0574(9) Uani 1 1 d . . .
H22A H 0.3623 0.5614 0.4450 0.069 Uiso 1 1 calc R . .
C23 C 0.2663(8) 0.5158(5) 0.6219(4) 0.0699(11) Uani 1 1 d . . .
H23 H 0.4038 0.5819 0.6840 0.084 Uiso 1 1 calc R . .
C24 C 0.0926(8) 0.4326(5) 0.6758(4) 0.0616(10) Uani 1 1 d . . .
C25 C -0.1099(9) 0.3368(5) 0.5787(4) 0.0609(10) Uani 1 1 d . . .
H25 H -0.2314 0.2800 0.6119 0.073 Uiso 1 1 calc R . .
C26 C -0.1378(7) 0.3226(4) 0.4357(4) 0.0498(8) Uani 1 1 d . . .
H26 H -0.2758 0.2568 0.3735 0.060 Uiso 1 1 calc R . .
C27 C 0.1195(12) 0.4456(7) 0.8334(5) 0.1016(17) Uani 1 1 d . . .
H27A H -0.0491 0.4693 0.8572 0.152 Uiso 1 1 calc R . .
H27B H 0.2482 0.5319 0.8835 0.152 Uiso 1 1 calc R . .
H27C H 0.1766 0.3439 0.8593 0.152 Uiso 1 1 calc R . .
H21 H -0.370(6) 0.278(4) 0.121(3) 0.045(9) Uiso 1 1 d . . .
H22 H -0.352(7) 0.459(5) 0.144(4) 0.058(11) Uiso 1 1 d . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S11 0.0342(4) 0.0264(4) 0.0506(7) 0.0097(5) 0.0151(5) 0.0010(3)
O11 0.0493(13) 0.0296(11) 0.0714(18) 0.0081(11) 0.0245(12) 0.0092(9)
O12 0.0504(12) 0.0304(11) 0.0572(15) 0.0129(10) 0.0199(11) -0.0032(9)
N11 0.0378(15) 0.0331(15) 0.0525(18) 0.0092(13) 0.0081(13) 0.0010(13)
C11 0.0358(16) 0.0324(16) 0.047(2) 0.0134(14) 0.0079(14) -0.0038(13)
C12 0.0446(19) 0.048(2) 0.068(3) 0.0191(17) 0.0062(17) 0.0028(15)
C13 0.060(2) 0.065(2) 0.070(3) 0.033(2) -0.009(2) -0.0025(19)
C14 0.073(3) 0.060(2) 0.050(2) 0.0190(19) 0.006(2) -0.019(2)
C15 0.064(2) 0.063(2) 0.053(2) 0.0085(17) 0.0219(18) -0.0020(18)
C16 0.0471(19) 0.0476(19) 0.054(2) 0.0141(16) 0.0122(15) 0.0085(15)
C17 0.139(5) 0.111(5) 0.056(3) 0.022(3) 0.001(3) -0.018(4)
S21 0.0365(4) 0.0290(5) 0.0541(8) 0.0134(5) 0.0170(5) 0.0029(4)
O21 0.0526(13) 0.0381(13) 0.0694(18) 0.0235(12) 0.0198(12) -0.0054(10)
O22 0.0519(13) 0.0368(12) 0.0674(17) 0.0130(11) 0.0259(12) 0.0121(10)
N21 0.0384(15) 0.0338(15) 0.0549(19) 0.0119(13) 0.0111(13) 0.0018(13)
C21 0.0353(16) 0.0293(16) 0.051(2) 0.0088(14) 0.0098(14) 0.0051(13)
C22 0.048(2) 0.057(2) 0.064(3) 0.0143(18) 0.0023(17) -0.0169(16)
C23 0.066(3) 0.070(3) 0.061(3) 0.006(2) -0.006(2) -0.020(2)
C24 0.076(3) 0.055(2) 0.051(2) 0.0092(18) 0.011(2) 0.007(2)
C25 0.072(3) 0.059(2) 0.055(3) 0.0119(19) 0.021(2) -0.0132(19)
C26 0.057(2) 0.0444(19) 0.048(2) 0.0053(15) 0.0135(16) -0.0145(16)
C27 0.141(5) 0.104(4) 0.054(3) 0.010(3) 0.014(3) -0.013(3)
_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
S11 O11 1.432(2) . ?
S11 O12 1.436(2) . ?
S11 N11 1.594(3) . ?
S11 C11 1.763(3) . ?
N11 H11 0.87(3) . ?
N11 H12 0.83(3) . ?
C11 C12 1.385(4) . ?
C11 C16 1.386(5) . ?
C12 C13 1.374(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.386(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(6) . ?
C14 C17 1.499(6) . ?
C15 C16 1.380(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
S21 O22 1.433(2) . ?
S21 O21 1.434(2) . ?
S21 N21 1.603(3) . ?
S21 C21 1.762(3) . ?
N21 H21 0.90(3) . ?
N21 H22 0.85(4) . ?
C21 C22 1.374(4) . ?
C21 C26 1.388(4) . ?
C22 C23 1.379(5) . ?
C22 H22A 0.9300 . ?
C23 C24 1.377(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(6) . ?
C24 C27 1.512(6) . ?
C25 C26 1.369(5) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
O11 S11 O12 117.18(13) . . ?
O11 S11 N11 108.06(15) . . ?
O12 S11 N11 107.38(15) . . ?
O11 S11 C11 107.62(14) . . ?
O12 S11 C11 107.80(13) . . ?
N11 S11 C11 108.56(14) . . ?
S11 N11 H11 115.5(19) . . ?
S11 N11 H12 115(2) . . ?
H11 N11 H12 114(3) . . ?
C12 C11 C16 119.3(3) . . ?
C12 C11 S11 119.9(3) . . ?
C16 C11 S11 120.6(2) . . ?
C13 C12 C11 119.9(3) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C12 C13 C14 121.8(3) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 117.4(4) . . ?
C15 C14 C17 121.2(4) . . ?
C13 C14 C17 121.3(4) . . ?
C16 C15 C14 121.9(4) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C11 119.6(3) . . ?
C15 C16 H16 120.2 . . ?
C11 C16 H16 120.2 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O22 S21 O21 118.03(14) . . ?
O22 S21 N21 107.27(15) . . ?
O21 S21 N21 107.79(14) . . ?
O22 S21 C21 107.32(14) . . ?
O21 S21 C21 106.93(14) . . ?
N21 S21 C21 109.30(14) . . ?
S21 N21 H21 114(2) . . ?
S21 N21 H22 109(2) . . ?
H21 N21 H22 117(3) . . ?
C22 C21 C26 119.0(3) . . ?
C22 C21 S21 119.7(3) . . ?
C26 C21 S21 121.3(2) . . ?
C21 C22 C23 120.3(3) . . ?
C21 C22 H22A 119.8 . . ?
C23 C22 H22A 119.8 . . ?
C24 C23 C22 121.8(3) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C23 C24 C25 116.8(4) . . ?
C23 C24 C27 121.9(4) . . ?
C25 C24 C27 121.4(4) . . ?
C26 C25 C24 122.5(4) . . ?
C26 C25 H25 118.8 . . ?
C24 C25 H25 118.8 . . ?
C25 C26 C21 119.6(3) . . ?
C25 C26 H26 120.2 . . ?
C21 C26 H26 120.2 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 S11 C11 C12 28.2(3) . . . . ?
O12 S11 C11 C12 -99.1(3) . . . . ?
N11 S11 C11 C12 144.9(3) . . . . ?
O11 S11 C11 C16 -156.4(2) . . . . ?
O12 S11 C11 C16 76.3(3) . . . . ?
N11 S11 C11 C16 -39.7(3) . . . . ?
C16 C11 C12 C13 1.0(5) . . . . ?
S11 C11 C12 C13 176.4(3) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C12 C13 C14 C15 0.4(5) . . . . ?
C12 C13 C14 C17 -179.1(4) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C17 C14 C15 C16 179.2(4) . . . . ?
C14 C15 C16 C11 0.4(5) . . . . ?
C12 C11 C16 C15 -0.8(5) . . . . ?
S11 C11 C16 C15 -176.2(2) . . . . ?
O22 S21 C21 C22 99.1(3) . . . . ?
O21 S21 C21 C22 -28.5(3) . . . . ?
N21 S21 C21 C22 -144.9(3) . . . . ?
O22 S21 C21 C26 -77.8(3) . . . . ?
O21 S21 C21 C26 154.6(2) . . . . ?
N21 S21 C21 C26 38.2(3) . . . . ?
C26 C21 C22 C23 0.4(5) . . . . ?
S21 C21 C22 C23 -176.6(3) . . . . ?
C21 C22 C23 C24 0.0(6) . . . . ?
C22 C23 C24 C25 -0.5(6) . . . . ?
C22 C23 C24 C27 179.9(4) . . . . ?
C23 C24 C25 C26 0.6(6) . . . . ?
C27 C24 C25 C26 -179.7(4) . . . . ?
C24 C25 C26 C21 -0.2(6) . . . . ?
C22 C21 C26 C25 -0.3(5) . . . . ?
S21 C21 C26 C25 176.7(3) . . . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N11 H11 O21 0.87(3) 2.32(3) 3.064(4) 144(3) .
N11 H11 O11 0.87(3) 2.63(3) 3.293(3) 134(2) 1_455
N11 H12 O22 0.83(3) 2.31(3) 3.056(4) 149(3) 1_565
N21 H22 O11 0.85(4) 2.24(4) 2.973(4) 145(3) 1_455
N21 H21 O12 0.90(3) 2.21(4) 3.025(4) 151(3) 1_445
N21 H21 O22 0.90(3) 2.67(3) 3.320(3) 130(3) 1_455
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.038