# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full CrystEngComm
_journal_coden_cambridge 1350
_journal_year 2011
_journal_volume ?
_journal_page_first ?
_publ_contact_author_name 'Nikolay Tumanov'
_publ_contact_author_email n.tumanov@gmail.com
loop_
_publ_author_name
N.Tumanov
S.Myz
T.Shakhtshneider
E.Boldyreva
data_mel_adip
_database_code_depnum_ccdc_archive 'CCDC 834808'
#TrackingRef '- mel_adip.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
4-Hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-
carboxamide 1,1-dioxide adipic acid
;
_chemical_name_common
;
4-Hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-
benzothiazine-3-carboxamide 1,1-dioxide adipic acid
;
_chemical_melting_point ?
_chemical_formula_moiety 'C14 H13 N3 O4 S2, 0.5(C6 H10 O4)'
_chemical_formula_sum 'C17 H18 N3 O6 S2'
_chemical_formula_weight 424.46
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'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.3589(9)
_cell_length_b 10.6257(12)
_cell_length_c 11.7957(13)
_cell_angle_alpha 80.019(10)
_cell_angle_beta 72.499(10)
_cell_angle_gamma 73.133(10)
_cell_volume 951.94(18)
_cell_formula_units_Z 2
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 2634
_cell_measurement_theta_min 3.5757
_cell_measurement_theta_max 28.1725
_exptl_crystal_description plate
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.29
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.03
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.481
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 442
_exptl_absorpt_coefficient_mu 0.320
_exptl_absorpt_correction_T_min 0.89725
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Oxford Diffraction Gemini Ultra R CCD'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 10.3457
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 11767
_diffrn_reflns_av_R_equivalents 0.0516
_diffrn_reflns_av_sigmaI/netI 0.0822
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_theta_min 3.58
_diffrn_reflns_theta_max 26.37
_reflns_number_total 3892
_reflns_number_gt 2218
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Mercury (Macrae et al., 2006)'
_computing_publication_material
;
publCIF (Westrip., 2008),
enCIFer (Allen et al., 2004).
;
_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^)+(0.0348P)^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_number_reflns 3892
_refine_ls_number_parameters 309
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0966
_refine_ls_R_factor_gt 0.0440
_refine_ls_wR_factor_ref 0.0846
_refine_ls_wR_factor_gt 0.0746
_refine_ls_goodness_of_fit_ref 0.855
_refine_ls_restrained_S_all 0.855
_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
S1 S 0.60394(8) 0.25626(6) 0.22318(6) 0.0431(2) Uani 1 1 d . . .
S2 S 0.83438(8) 0.82127(6) 0.15132(7) 0.0440(2) Uani 1 1 d . . .
C1 C 0.3476(6) 0.1234(4) 0.2459(4) 0.0655(10) Uani 1 1 d . . .
H1B H 0.400(4) 0.045(4) 0.287(3) 0.105(15) Uiso 1 1 d . . .
H1C H 0.229(4) 0.131(3) 0.274(3) 0.075(10) Uiso 1 1 d . . .
H1A H 0.371(4) 0.122(3) 0.166(3) 0.085(13) Uiso 1 1 d . . .
C2 C 0.3944(3) 0.2392(3) 0.2739(2) 0.0418(6) Uani 1 1 d . . .
C3 C 0.2912(4) 0.3418(3) 0.3317(2) 0.0425(7) Uani 1 1 d . . .
H3 H 0.173(3) 0.355(2) 0.3665(18) 0.033(6) Uiso 1 1 d . . .
C4 C 0.5324(3) 0.4053(2) 0.2835(2) 0.0345(6) Uani 1 1 d . . .
C5 C 0.8080(3) 0.4638(2) 0.2111(2) 0.0353(6) Uani 1 1 d . . .
C6 C 0.8962(3) 0.5690(2) 0.1940(2) 0.0326(6) Uani 1 1 d . . .
C7 C 1.0640(3) 0.5534(2) 0.1303(2) 0.0343(6) Uani 1 1 d . . .
C8 C 1.1551(3) 0.6577(2) 0.1118(2) 0.0348(6) Uani 1 1 d . . .
C9 C 1.3335(3) 0.6283(3) 0.0892(2) 0.0432(7) Uani 1 1 d . . .
H9 H 1.3985 0.5412 0.0826 0.052 Uiso 1 1 calc R . .
C10 C 1.4153(4) 0.7270(3) 0.0763(2) 0.0499(7) Uani 1 1 d . . .
H10 H 1.5353 0.7063 0.0613 0.060 Uiso 1 1 calc R . .
C11 C 1.3206(4) 0.8562(3) 0.0856(2) 0.0543(8) Uani 1 1 d . . .
H11 H 1.3776 0.9221 0.0765 0.065 Uiso 1 1 calc R . .
C12 C 1.1428(3) 0.8893(3) 0.1082(2) 0.0477(7) Uani 1 1 d . . .
H12 H 1.0791 0.9767 0.1150 0.057 Uiso 1 1 calc R . .
C13 C 1.0603(3) 0.7890(2) 0.1207(2) 0.0377(6) Uani 1 1 d . . .
C14 C 0.7992(5) 0.6963(4) 0.3680(3) 0.0558(8) Uani 1 1 d . . .
H14A H 0.917(4) 0.689(2) 0.371(2) 0.058(9) Uiso 1 1 d . . .
H14C H 0.760(3) 0.619(3) 0.420(2) 0.073(10) Uiso 1 1 d . . .
H14B H 0.725(4) 0.777(3) 0.397(2) 0.072(10) Uiso 1 1 d . . .
C15 C 0.2778(4) 0.7279(3) 0.4563(3) 0.0510(7) Uani 1 1 d . . .
C16 C 0.1810(4) 0.8454(3) 0.5248(3) 0.0540(8) Uani 1 1 d . . .
H16A H 0.263(3) 0.894(2) 0.523(2) 0.061(9) Uiso 1 1 d . . .
H16B H 0.135(4) 0.819(3) 0.607(3) 0.070(10) Uiso 1 1 d . . .
C17 C 0.0395(4) 0.9352(3) 0.4721(3) 0.0455(7) Uani 1 1 d . . .
H17A H -0.057(3) 0.892(2) 0.4844(18) 0.041(7) Uiso 1 1 d . . .
H17B H 0.089(3) 0.952(2) 0.386(2) 0.048(8) Uiso 1 1 d . . .
O1 O 1.1604(2) 0.44291(18) 0.07888(16) 0.0446(5) Uani 1 1 d . . .
H1 H 1.095(5) 0.391(4) 0.095(3) 0.112(15) Uiso 1 1 d . . .
O2 O 0.8864(2) 0.35507(16) 0.17290(15) 0.0456(5) Uani 1 1 d . . .
O3 O 0.7897(2) 0.81293(17) 0.04517(16) 0.0532(5) Uani 1 1 d . . .
O4 O 0.7547(2) 0.93562(16) 0.21452(19) 0.0642(6) Uani 1 1 d . . .
O5 O 0.4218(3) 0.7143(2) 0.3950(2) 0.0928(8) Uani 1 1 d . . .
O6 O 0.1883(3) 0.6416(2) 0.4676(2) 0.0695(7) Uani 1 1 d . . .
H6 H 0.252(5) 0.573(4) 0.416(4) 0.140(16) Uiso 1 1 d . . .
N1 N 0.3681(3) 0.4385(2) 0.33926(18) 0.0399(5) Uani 1 1 d . . .
N2 N 0.6373(3) 0.4901(2) 0.27036(19) 0.0382(5) Uani 1 1 d . . .
H2 H 0.586(3) 0.566(2) 0.297(2) 0.049(8) Uiso 1 1 d . . .
N3 N 0.7981(2) 0.69186(19) 0.24367(17) 0.0368(5) Uani 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
S1 0.0433(4) 0.0362(4) 0.0522(5) -0.0118(3) -0.0066(3) -0.0157(3)
S2 0.0362(4) 0.0298(4) 0.0666(5) -0.0045(3) -0.0128(4) -0.0103(3)
C1 0.065(3) 0.064(3) 0.078(3) -0.022(2) -0.006(2) -0.036(2)
C2 0.0434(16) 0.0404(16) 0.0451(17) -0.0064(13) -0.0080(13) -0.0186(14)
C3 0.0390(17) 0.0440(17) 0.0473(17) -0.0045(14) -0.0060(14) -0.0203(15)
C4 0.0394(15) 0.0296(14) 0.0371(15) -0.0004(12) -0.0113(12) -0.0131(13)
C5 0.0382(15) 0.0323(15) 0.0365(15) -0.0006(12) -0.0111(12) -0.0108(13)
C6 0.0344(14) 0.0278(14) 0.0368(15) -0.0044(11) -0.0092(12) -0.0093(12)
C7 0.0364(14) 0.0326(15) 0.0358(15) -0.0042(12) -0.0120(12) -0.0086(13)
C8 0.0368(14) 0.0383(15) 0.0336(15) -0.0031(12) -0.0118(12) -0.0137(13)
C9 0.0340(15) 0.0529(18) 0.0430(17) -0.0045(13) -0.0099(12) -0.0118(14)
C10 0.0387(16) 0.066(2) 0.0518(18) -0.0081(15) -0.0117(14) -0.0224(16)
C11 0.0549(19) 0.070(2) 0.0542(19) -0.0087(16) -0.0110(15) -0.0421(19)
C12 0.0535(19) 0.0419(16) 0.0543(18) -0.0055(14) -0.0104(14) -0.0254(15)
C13 0.0385(15) 0.0386(16) 0.0410(16) -0.0044(12) -0.0124(12) -0.0153(13)
C14 0.063(2) 0.058(2) 0.050(2) -0.0192(18) -0.0074(17) -0.022(2)
C15 0.0448(18) 0.0400(18) 0.069(2) -0.0157(15) -0.0185(16) -0.0019(16)
C16 0.052(2) 0.0426(19) 0.069(2) -0.0178(17) -0.0224(18) -0.0002(16)
C17 0.0424(17) 0.0375(16) 0.055(2) -0.0122(14) -0.0089(15) -0.0075(14)
O1 0.0393(10) 0.0331(11) 0.0585(13) -0.0119(9) -0.0096(9) -0.0038(10)
O2 0.0439(10) 0.0297(10) 0.0602(12) -0.0116(9) -0.0039(9) -0.0107(9)
O3 0.0501(11) 0.0494(12) 0.0677(13) 0.0100(10) -0.0298(10) -0.0183(10)
O4 0.0492(11) 0.0312(11) 0.1070(17) -0.0225(11) -0.0058(11) -0.0082(9)
O5 0.0484(13) 0.0727(16) 0.151(2) -0.0615(16) 0.0172(14) -0.0224(12)
O6 0.0496(13) 0.0517(14) 0.1026(18) -0.0320(13) 0.0022(12) -0.0147(12)
N1 0.0392(13) 0.0368(13) 0.0441(13) -0.0059(10) -0.0049(11) -0.0155(11)
N2 0.0366(13) 0.0276(13) 0.0518(14) -0.0090(11) -0.0074(11) -0.0115(11)
N3 0.0374(12) 0.0307(12) 0.0433(13) -0.0094(10) -0.0051(10) -0.0123(10)
_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
S1 C4 1.719(2) . ?
S1 C2 1.725(2) . ?
S2 O4 1.4217(18) . ?
S2 O3 1.4333(18) . ?
S2 N3 1.641(2) . ?
S2 C13 1.753(2) . ?
C1 C2 1.508(4) . ?
C1 H1B 0.94(4) . ?
C1 H1C 0.93(3) . ?
C1 H1A 0.90(3) . ?
C2 C3 1.325(3) . ?
C3 N1 1.388(3) . ?
C3 H3 0.93(2) . ?
C4 N1 1.303(3) . ?
C4 N2 1.391(3) . ?
C5 O2 1.237(3) . ?
C5 N2 1.356(3) . ?
C5 C6 1.464(3) . ?
C6 C7 1.354(3) . ?
C6 N3 1.440(3) . ?
C7 O1 1.341(3) . ?
C7 C8 1.470(3) . ?
C8 C9 1.383(3) . ?
C8 C13 1.395(3) . ?
C9 C10 1.375(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(3) . ?
C12 H12 0.9300 . ?
C14 N3 1.479(3) . ?
C14 H14A 0.97(3) . ?
C14 H14C 1.01(3) . ?
C14 H14B 0.95(3) . ?
C15 O5 1.186(3) . ?
C15 O6 1.309(3) . ?
C15 C16 1.495(4) . ?
C16 C17 1.509(4) . ?
C16 H16A 0.96(2) . ?
C16 H16B 0.95(3) . ?
C17 C17 1.513(5) 2_576 ?
C17 H17A 1.00(2) . ?
C17 H17B 0.98(2) . ?
O1 H1 0.85(3) . ?
O6 H6 0.95(4) . ?
N2 H2 0.86(2) . ?
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
C4 S1 C2 88.63(12) . . ?
O4 S2 O3 119.88(12) . . ?
O4 S2 N3 108.30(11) . . ?
O3 S2 N3 107.28(10) . . ?
O4 S2 C13 109.58(11) . . ?
O3 S2 C13 109.18(11) . . ?
N3 S2 C13 100.92(11) . . ?
C2 C1 H1B 109(2) . . ?
C2 C1 H1C 111.2(18) . . ?
H1B C1 H1C 105(3) . . ?
C2 C1 H1A 111(2) . . ?
H1B C1 H1A 116(3) . . ?
H1C C1 H1A 105(3) . . ?
C3 C2 C1 128.7(3) . . ?
C3 C2 S1 110.17(19) . . ?
C1 C2 S1 121.1(2) . . ?
C2 C3 N1 116.5(2) . . ?
C2 C3 H3 126.0(14) . . ?
N1 C3 H3 117.5(14) . . ?
N1 C4 N2 120.8(2) . . ?
N1 C4 S1 115.57(18) . . ?
N2 C4 S1 123.60(19) . . ?
O2 C5 N2 121.3(2) . . ?
O2 C5 C6 121.2(2) . . ?
N2 C5 C6 117.5(2) . . ?
C7 C6 N3 120.5(2) . . ?
C7 C6 C5 121.2(2) . . ?
N3 C6 C5 118.2(2) . . ?
O1 C7 C6 123.3(2) . . ?
O1 C7 C8 114.5(2) . . ?
C6 C7 C8 122.2(2) . . ?
C9 C8 C13 118.8(2) . . ?
C9 C8 C7 121.4(2) . . ?
C13 C8 C7 119.8(2) . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.4(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 120.9(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 118.6(3) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C12 C13 C8 121.0(2) . . ?
C12 C13 S2 121.9(2) . . ?
C8 C13 S2 117.15(18) . . ?
N3 C14 H14A 109.6(15) . . ?
N3 C14 H14C 110.0(15) . . ?
H14A C14 H14C 108(2) . . ?
N3 C14 H14B 110.2(17) . . ?
H14A C14 H14B 109(2) . . ?
H14C C14 H14B 110(2) . . ?
O5 C15 O6 122.4(3) . . ?
O5 C15 C16 123.5(3) . . ?
O6 C15 C16 114.2(3) . . ?
C15 C16 C17 112.3(2) . . ?
C15 C16 H16A 107.6(15) . . ?
C17 C16 H16A 109.3(15) . . ?
C15 C16 H16B 110.9(17) . . ?
C17 C16 H16B 110.8(17) . . ?
H16A C16 H16B 106(2) . . ?
C16 C17 C17 112.6(3) . 2_576 ?
C16 C17 H17A 110.8(13) . . ?
C17 C17 H17A 106.8(13) 2_576 . ?
C16 C17 H17B 108.4(14) . . ?
C17 C17 H17B 109.6(14) 2_576 . ?
H17A C17 H17B 108.3(18) . . ?
C7 O1 H1 106(2) . . ?
C15 O6 H6 110(2) . . ?
C4 N1 C3 109.1(2) . . ?
C5 N2 C4 124.1(2) . . ?
C5 N2 H2 119.5(16) . . ?
C4 N2 H2 116.2(16) . . ?
C6 N3 C14 114.5(2) . . ?
C6 N3 S2 112.68(15) . . ?
C14 N3 S2 115.66(18) . . ?
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
C4 S1 C2 C3 -1.0(2) . . . . ?
C4 S1 C2 C1 176.2(3) . . . . ?
C1 C2 C3 N1 -176.6(3) . . . . ?
S1 C2 C3 N1 0.3(3) . . . . ?
C2 S1 C4 N1 1.6(2) . . . . ?
C2 S1 C4 N2 -175.4(2) . . . . ?
O2 C5 C6 C7 3.7(4) . . . . ?
N2 C5 C6 C7 -176.4(2) . . . . ?
O2 C5 C6 N3 -178.3(2) . . . . ?
N2 C5 C6 N3 1.6(3) . . . . ?
N3 C6 C7 O1 -177.9(2) . . . . ?
C5 C6 C7 O1 0.0(4) . . . . ?
N3 C6 C7 C8 1.9(4) . . . . ?
C5 C6 C7 C8 179.8(2) . . . . ?
O1 C7 C8 C9 -25.4(3) . . . . ?
C6 C7 C8 C9 154.8(2) . . . . ?
O1 C7 C8 C13 156.7(2) . . . . ?
C6 C7 C8 C13 -23.1(3) . . . . ?
C13 C8 C9 C10 0.3(4) . . . . ?
C7 C8 C9 C10 -177.7(2) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C11 C12 C13 C8 0.6(4) . . . . ?
C11 C12 C13 S2 179.2(2) . . . . ?
C9 C8 C13 C12 -0.5(4) . . . . ?
C7 C8 C13 C12 177.5(2) . . . . ?
C9 C8 C13 S2 -179.21(18) . . . . ?
C7 C8 C13 S2 -1.2(3) . . . . ?
O4 S2 C13 C12 -27.7(2) . . . . ?
O3 S2 C13 C12 105.4(2) . . . . ?
N3 S2 C13 C12 -141.8(2) . . . . ?
O4 S2 C13 C8 150.97(19) . . . . ?
O3 S2 C13 C8 -75.9(2) . . . . ?
N3 S2 C13 C8 36.9(2) . . . . ?
O5 C15 C16 C17 108.0(4) . . . . ?
O6 C15 C16 C17 -70.6(4) . . . . ?
C15 C16 C17 C17 -170.6(3) . . . 2_576 ?
N2 C4 N1 C3 175.4(2) . . . . ?
S1 C4 N1 C3 -1.7(3) . . . . ?
C2 C3 N1 C4 0.9(3) . . . . ?
O2 C5 N2 C4 -6.5(4) . . . . ?
C6 C5 N2 C4 173.5(2) . . . . ?
N1 C4 N2 C5 -178.3(2) . . . . ?
S1 C4 N2 C5 -1.5(3) . . . . ?
C7 C6 N3 C14 -93.3(3) . . . . ?
C5 C6 N3 C14 88.7(3) . . . . ?
C7 C6 N3 S2 41.6(3) . . . . ?
C5 C6 N3 S2 -136.40(18) . . . . ?
O4 S2 N3 C6 -170.73(15) . . . . ?
O3 S2 N3 C6 58.55(18) . . . . ?
C13 S2 N3 C6 -55.69(17) . . . . ?
O4 S2 N3 C14 -36.4(2) . . . . ?
O3 S2 N3 C14 -167.1(2) . . . . ?
C13 S2 N3 C14 78.7(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 26.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.234
_refine_diff_density_min -0.251
_refine_diff_density_rms 0.043
_iucr_refine_instructions_details
;
TITL MEL_TEST2A IN P1
CELL 0.71073 8.35890 10.62570 11.79570 80.01900 72.49900 73.13300
ZERR 2 0.00090 0.00120 0.00130 0.01000 0.01000 0.01000
LATT 1
SFAC C H O S N
UNIT 34 36 12 4 6
SHEL 20 0.8
BOND $H
ACTA
CONF
HTAB O1 O2
HTAB N2 O5
HTAB N2 N3
HTAB O6 N1
PLAN 30
FMAP 2
L.S. 10
WGHT 0.034800
FVAR 2.00561
S1 4 0.603938 0.256258 0.223179 11.00000 0.04331 0.03625 =
0.05224 -0.01175 -0.00656 -0.01568
S2 4 0.834376 0.821266 0.151324 11.00000 0.03620 0.02981 =
0.06664 -0.00446 -0.01279 -0.01033
C1 1 0.347623 0.123353 0.245879 11.00000 0.06451 0.06441 =
0.07772 -0.02208 -0.00636 -0.03558
H1B 2 0.399728 0.045437 0.287080 11.00000 0.10546
H1C 2 0.228614 0.131103 0.273833 11.00000 0.07507
H1A 2 0.371332 0.121765 0.166076 11.00000 0.08492
C2 1 0.394352 0.239151 0.273878 11.00000 0.04344 0.04044 =
0.04507 -0.00637 -0.00798 -0.01858
C3 1 0.291220 0.341781 0.331697 11.00000 0.03895 0.04398 =
0.04730 -0.00448 -0.00600 -0.02029
H3 2 0.172656 0.355041 0.366510 11.00000 0.03330
C4 1 0.532395 0.405309 0.283452 11.00000 0.03935 0.02960 =
0.03715 -0.00041 -0.01128 -0.01307
C5 1 0.808029 0.463807 0.211057 11.00000 0.03818 0.03232 =
0.03648 -0.00062 -0.01112 -0.01080
C6 1 0.896184 0.569024 0.194027 11.00000 0.03438 0.02784 =
0.03677 -0.00443 -0.00921 -0.00928
C7 1 1.063976 0.553358 0.130297 11.00000 0.03643 0.03261 =
0.03576 -0.00423 -0.01204 -0.00855
C8 1 1.155060 0.657684 0.111759 11.00000 0.03681 0.03833 =
0.03360 -0.00310 -0.01180 -0.01366
C9 1 1.333517 0.628285 0.089160 11.00000 0.03399 0.05289 =
0.04304 -0.00455 -0.00995 -0.01183
AFIX 43
H9 2 1.398543 0.541225 0.082609 11.00000 -1.20000
AFIX 0
C10 1 1.415318 0.726998 0.076326 11.00000 0.03867 0.06606 =
0.05177 -0.00814 -0.01170 -0.02241
AFIX 43
H10 2 1.535345 0.706321 0.061290 11.00000 -1.20000
AFIX 0
C11 1 1.320628 0.856231 0.085600 11.00000 0.05493 0.06975 =
0.05418 -0.00868 -0.01096 -0.04207
AFIX 43
H11 2 1.377562 0.922138 0.076456 11.00000 -1.20000
AFIX 0
C12 1 1.142841 0.889319 0.108220 11.00000 0.05352 0.04188 =
0.05427 -0.00550 -0.01045 -0.02545
AFIX 43
H12 2 1.079132 0.976676 0.115019 11.00000 -1.20000
AFIX 0
C13 1 1.060318 0.789046 0.120722 11.00000 0.03853 0.03862 =
0.04103 -0.00437 -0.01239 -0.01527
C14 1 0.799202 0.696312 0.368025 11.00000 0.06338 0.05841 =
0.05035 -0.01917 -0.00737 -0.02230
H14A 2 0.916818 0.688885 0.370976 11.00000 0.05806
H14C 2 0.759549 0.619488 0.420312 11.00000 0.07301
H14B 2 0.725310 0.777133 0.397286 11.00000 0.07161
C15 1 0.277788 0.727946 0.456331 11.00000 0.04483 0.04003 =
0.06854 -0.01568 -0.01848 -0.00188
C16 1 0.180994 0.845411 0.524822 11.00000 0.05232 0.04264 =
0.06853 -0.01784 -0.02239 -0.00019
H16A 2 0.263428 0.893542 0.523293 11.00000 0.06058
H16B 2 0.135330 0.818891 0.606985 11.00000 0.06961
C17 1 0.039475 0.935216 0.472100 11.00000 0.04245 0.03750 =
0.05515 -0.01221 -0.00892 -0.00748
H17A 2 -0.057238 0.892459 0.484399 11.00000 0.04055
H17B 2 0.088585 0.952347 0.385874 11.00000 0.04807
O1 3 1.160447 0.442906 0.078878 11.00000 0.03930 0.03307 =
0.05851 -0.01194 -0.00957 -0.00381
H1 2 1.094531 0.390863 0.094871 11.00000 0.11207
O2 3 0.886386 0.355067 0.172904 11.00000 0.04392 0.02970 =
0.06020 -0.01156 -0.00394 -0.01067
O3 3 0.789677 0.812930 0.045171 11.00000 0.05014 0.04938 =
0.06773 0.00997 -0.02982 -0.01828
O4 3 0.754734 0.935616 0.214518 11.00000 0.04919 0.03116 =
0.10698 -0.02249 -0.00582 -0.00822
O5 3 0.421833 0.714328 0.394988 11.00000 0.04836 0.07269 =
0.15148 -0.06147 0.01718 -0.02244
O6 3 0.188307 0.641617 0.467639 11.00000 0.04960 0.05169 =
0.10264 -0.03200 0.00220 -0.01470
H6 2 0.252115 0.573425 0.416165 11.00000 0.14034
N1 5 0.368132 0.438461 0.339259 11.00000 0.03915 0.03683 =
0.04409 -0.00592 -0.00490 -0.01554
N2 5 0.637325 0.490095 0.270364 11.00000 0.03657 0.02757 =
0.05176 -0.00896 -0.00740 -0.01146
H2 2 0.586353 0.565961 0.296962 11.00000 0.04950
N3 5 0.798131 0.691858 0.243669 11.00000 0.03741 0.03072 =
0.04327 -0.00943 -0.00511 -0.01234
HKLF 4
REM MEL_TEST2A IN P1
REM R1 = 0.0440 for 2218 Fo > 4sig(Fo) and 0.0966 for all 3892 data
REM 309 parameters refined using 0 restraints
END
WGHT 0.0348 0.0000
REM Highest difference peak 0.234, deepest hole -0.251, 1-sigma level 0.043
Q1 1 0.5757 0.4399 0.2709 11.00000 0.05 0.23
Q2 1 0.4253 0.6385 0.4696 11.00000 0.05 0.20
Q3 1 0.9495 0.5846 0.1315 11.00000 0.05 0.20
Q4 1 0.5756 0.3351 0.2645 11.00000 0.05 0.20
Q5 1 0.3558 0.7201 0.3564 11.00000 0.05 0.19
Q6 1 0.5592 0.3694 0.2068 11.00000 0.05 0.19
Q7 1 0.8493 0.5396 0.1840 11.00000 0.05 0.18
Q8 1 0.8111 0.7497 0.2072 11.00000 0.05 0.17
Q9 1 0.3234 0.4828 0.4022 11.00000 0.05 0.17
Q10 1 0.2084 0.6849 0.3842 11.00000 0.05 0.16
Q11 1 1.1123 0.6179 0.1229 11.00000 0.05 0.16
Q12 1 0.3389 0.3975 0.3557 11.00000 0.05 0.16
Q13 1 1.1077 0.8222 0.1228 11.00000 0.05 0.15
Q14 1 0.2619 0.6229 0.4995 11.00000 0.05 0.15
Q15 1 1.0961 0.5054 0.1210 11.00000 0.05 0.15
Q16 1 0.7192 0.8605 0.1059 11.00000 0.05 0.15
Q17 1 1.2069 0.3752 -0.0038 11.00000 0.05 0.15
Q18 1 0.9354 0.3513 0.0929 11.00000 0.05 0.15
Q19 1 0.6615 0.2583 0.1231 11.00000 0.05 0.14
Q20 1 0.4962 0.7194 0.2954 11.00000 0.05 0.14
Q21 1 0.9663 0.7858 0.1354 11.00000 0.05 0.14
Q22 1 0.4064 0.1827 0.2636 11.00000 0.05 0.14
Q23 1 0.7902 0.1296 0.1607 11.00000 0.05 0.14
Q24 1 1.1057 0.7230 0.1097 11.00000 0.05 0.14
Q25 1 0.1313 0.8998 0.4944 11.00000 0.05 0.14
Q26 1 0.7340 0.8829 0.0807 11.00000 0.05 0.14
Q27 1 0.4054 -0.0630 0.3608 11.00000 0.05 0.14
Q28 1 1.2805 0.4233 0.1218 11.00000 0.05 0.14
Q29 1 0.4197 0.3608 0.4318 11.00000 0.05 0.14
Q30 1 0.8607 0.6205 0.2334 11.00000 0.05 0.13
;
# Attachment '- mel_tereph.cif'
data_mel_tereph
_database_code_depnum_ccdc_archive 'CCDC 834809'
#TrackingRef '- mel_tereph.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
4-Hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-
carboxamide 1,1-dioxide terephtalic acid
;
_chemical_name_common
;
4-Hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-
benzothiazine-3-carboxamide 1,1-dioxide terephtalic acid
;
_chemical_melting_point ?
_chemical_formula_moiety 'C14 H13 N3 O4 S2, 0.5(C8 H6 O4)'
_chemical_formula_sum 'C18 H16 N3 O6 S2'
_chemical_formula_weight 434.46
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
_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'
_cell_length_a 8.5979(6)
_cell_length_b 10.4551(6)
_cell_length_c 11.7515(7)
_cell_angle_alpha 91.355(5)
_cell_angle_beta 107.856(6)
_cell_angle_gamma 109.444(6)
_cell_volume 938.79(12)
_cell_formula_units_Z 2
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 4132
_cell_measurement_theta_min 3.6043
_cell_measurement_theta_max 31.7462
_exptl_crystal_description prizm
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.13
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.537
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 450
_exptl_absorpt_coefficient_mu 0.327
_exptl_absorpt_correction_T_min 0.97318
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.48
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Oxford Diffraction Gemini Ultra R CCD'
_diffrn_measurement_method \w
_diffrn_detector_area_resol_mean 10.3457
_diffrn_reflns_number 17934
_diffrn_reflns_av_R_equivalents 0.0510
_diffrn_reflns_av_sigmaI/netI 0.0703
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 3.61
_diffrn_reflns_theta_max 30.51
_reflns_number_total 5721
_reflns_number_gt 3365
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'CrysAlis CCD (Oxford Diffraction, 2008)'
_computing_cell_refinement 'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_data_reduction 'CrysAlis RED (Oxford Diffraction, 2008)'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Mercury (Macrae et al., 2006)'
_computing_publication_material
;
publCIF (Westrip., 2008),
enCIFer (Allen et al., 2004).
;
_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^)+(0.0422P)^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_number_reflns 5721
_refine_ls_number_parameters 326
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0896
_refine_ls_R_factor_gt 0.0432
_refine_ls_wR_factor_ref 0.0954
_refine_ls_wR_factor_gt 0.0855
_refine_ls_goodness_of_fit_ref 0.876
_refine_ls_restrained_S_all 0.876
_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
S1 S 0.81131(6) 0.76219(4) 0.22622(4) 0.03637(13) Uani 1 1 d . . .
S2 S 0.96719(6) 0.18694(4) 0.16582(5) 0.03994(14) Uani 1 1 d . . .
C1 C 0.5649(4) 0.8824(2) 0.2378(2) 0.0478(6) Uani 1 1 d . . .
H1A H 0.641(3) 0.966(2) 0.271(2) 0.064(7) Uiso 1 1 d . . .
H1B H 0.472(3) 0.873(2) 0.2692(19) 0.060(6) Uiso 1 1 d . . .
H1C H 0.523(3) 0.882(2) 0.147(2) 0.081(8) Uiso 1 1 d . . .
C2 C 0.6404(2) 0.77255(18) 0.26999(16) 0.0347(4) Uani 1 1 d . . .
C3 C 0.5851(2) 0.66564(18) 0.32675(17) 0.0347(4) Uani 1 1 d . . .
H3 H 0.492(2) 0.6476(18) 0.3614(16) 0.039(5) Uiso 1 1 d . . .
C4 C 0.7885(2) 0.61013(16) 0.28437(15) 0.0287(4) Uani 1 1 d . . .
C5 C 0.9993(2) 0.55519(17) 0.21426(16) 0.0310(4) Uani 1 1 d . . .
C6 C 1.0698(2) 0.44900(16) 0.20028(15) 0.0288(4) Uani 1 1 d . . .
C7 C 1.1760(2) 0.46125(16) 0.13309(15) 0.0292(4) Uani 1 1 d . . .
C8 C 1.2451(2) 0.35395(17) 0.11564(15) 0.0302(4) Uani 1 1 d . . .
C9 C 1.3991(2) 0.3839(2) 0.08918(16) 0.0369(4) Uani 1 1 d . . .
H9 H 1.460(2) 0.4785(18) 0.0844(15) 0.034(5) Uiso 1 1 d . . .
C10 C 1.4657(3) 0.2823(2) 0.07817(18) 0.0441(5) Uani 1 1 d . . .
H10 H 1.572(3) 0.310(2) 0.0610(18) 0.051(6) Uiso 1 1 d . . .
C11 C 1.3786(3) 0.1498(2) 0.09144(19) 0.0477(5) Uani 1 1 d . . .
H11 H 1.421(2) 0.077(2) 0.0809(18) 0.051(6) Uiso 1 1 d . . .
C12 C 1.2251(3) 0.1167(2) 0.11781(19) 0.0437(5) Uani 1 1 d . . .
H12 H 1.164(2) 0.0283(19) 0.1288(16) 0.041(5) Uiso 1 1 d . . .
C13 C 1.1589(2) 0.21900(18) 0.12959(16) 0.0344(4) Uani 1 1 d . . .
C14 C 1.1271(3) 0.3386(3) 0.3829(2) 0.0430(5) Uani 1 1 d . . .
H14A H 1.129(2) 0.420(2) 0.4269(18) 0.047(6) Uiso 1 1 d . . .
H14B H 1.081(3) 0.262(2) 0.4131(17) 0.050(6) Uiso 1 1 d . . .
H14C H 1.248(3) 0.348(2) 0.3881(19) 0.070(7) Uiso 1 1 d . . .
O1 O 1.22477(17) 0.56963(13) 0.07617(12) 0.0386(3) Uani 1 1 d . . .
H1 H 1.177(3) 0.623(2) 0.1001(19) 0.055(7) Uiso 1 1 d . . .
O2 O 1.04166(17) 0.66384(12) 0.17179(12) 0.0419(3) Uani 1 1 d . . .
O3 O 0.82635(17) 0.18189(13) 0.05993(13) 0.0528(4) Uani 1 1 d . . .
O4 O 0.94778(19) 0.07662(13) 0.23485(15) 0.0598(4) Uani 1 1 d . . .
O5 O 0.78591(19) 0.30891(15) 0.42518(17) 0.0697(5) Uani 1 1 d . . .
O6 O 0.53431(18) 0.33394(14) 0.40547(14) 0.0479(4) Uani 1 1 d . . .
H6 H 0.581(3) 0.408(3) 0.381(3) 0.098(10) Uiso 1 1 d . . .
N1 N 0.66860(19) 0.57164(14) 0.33517(13) 0.0320(3) Uani 1 1 d . . .
N2 N 0.88283(19) 0.52820(15) 0.27463(14) 0.0323(3) Uani 1 1 d . . .
H2 H 0.859(3) 0.456(2) 0.3048(17) 0.046(6) Uiso 1 1 d . . .
N3 N 1.01715(18) 0.32803(14) 0.25546(13) 0.0317(3) Uani 1 1 d . . .
C15 C 0.6402(2) 0.26546(18) 0.43081(17) 0.0375(4) Uani 1 1 d . . .
C16 C 0.5656(2) 0.12891(17) 0.46756(16) 0.0321(4) Uani 1 1 d . . .
C17 C 0.3870(3) 0.06351(19) 0.44119(18) 0.0384(5) Uani 1 1 d . . .
H17 H 0.312(2) 0.1036(18) 0.4010(17) 0.042(5) Uiso 1 1 d . . .
C18 C 0.6785(3) 0.06450(19) 0.52669(19) 0.0393(5) Uani 1 1 d . . .
H18 H 0.798(3) 0.108(2) 0.5469(17) 0.050(6) 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
S1 0.0453(3) 0.0275(2) 0.0489(3) 0.0144(2) 0.0252(2) 0.0194(2)
S2 0.0379(3) 0.0237(2) 0.0627(3) 0.0078(2) 0.0226(3) 0.0112(2)
C1 0.0615(15) 0.0373(12) 0.0657(17) 0.0162(12) 0.0331(13) 0.0327(12)
C2 0.0414(10) 0.0310(9) 0.0393(11) 0.0070(8) 0.0153(9) 0.0207(8)
C3 0.0401(11) 0.0337(9) 0.0401(11) 0.0072(8) 0.0201(9) 0.0191(8)
C4 0.0329(9) 0.0237(8) 0.0318(9) 0.0064(7) 0.0111(8) 0.0126(7)
C5 0.0327(9) 0.0271(9) 0.0366(10) 0.0060(8) 0.0136(8) 0.0130(8)
C6 0.0305(9) 0.0241(8) 0.0348(10) 0.0074(7) 0.0125(8) 0.0119(7)
C7 0.0296(9) 0.0249(8) 0.0329(10) 0.0069(7) 0.0102(8) 0.0094(7)
C8 0.0324(9) 0.0335(9) 0.0277(9) 0.0049(8) 0.0105(8) 0.0148(8)
C9 0.0377(11) 0.0425(11) 0.0350(11) 0.0068(9) 0.0162(9) 0.0162(9)
C10 0.0433(12) 0.0598(14) 0.0405(12) 0.0061(10) 0.0196(10) 0.0274(11)
C11 0.0559(13) 0.0550(13) 0.0478(13) 0.0057(11) 0.0195(11) 0.0371(12)
C12 0.0546(13) 0.0342(11) 0.0504(13) 0.0053(10) 0.0201(11) 0.0235(10)
C13 0.0368(10) 0.0320(9) 0.0399(11) 0.0059(8) 0.0148(9) 0.0172(8)
C14 0.0421(12) 0.0532(14) 0.0440(13) 0.0200(11) 0.0181(10) 0.0253(11)
O1 0.0457(8) 0.0317(7) 0.0504(8) 0.0177(6) 0.0272(7) 0.0178(6)
O2 0.0531(8) 0.0286(7) 0.0605(9) 0.0181(6) 0.0337(7) 0.0207(6)
O3 0.0358(8) 0.0438(8) 0.0669(10) -0.0080(7) 0.0057(7) 0.0111(7)
O4 0.0683(10) 0.0303(7) 0.1037(13) 0.0282(8) 0.0530(10) 0.0226(7)
O5 0.0499(9) 0.0565(10) 0.1328(15) 0.0562(10) 0.0558(10) 0.0303(8)
O6 0.0471(8) 0.0383(8) 0.0799(11) 0.0312(8) 0.0385(8) 0.0249(7)
N1 0.0382(8) 0.0288(7) 0.0363(9) 0.0099(7) 0.0172(7) 0.0162(7)
N2 0.0382(9) 0.0252(8) 0.0427(9) 0.0117(7) 0.0194(7) 0.0169(7)
N3 0.0365(8) 0.0266(7) 0.0408(9) 0.0124(7) 0.0185(7) 0.0166(6)
C15 0.0414(11) 0.0344(10) 0.0473(12) 0.0155(9) 0.0240(9) 0.0176(9)
C16 0.0358(10) 0.0267(9) 0.0397(11) 0.0100(8) 0.0185(9) 0.0128(8)
C17 0.0397(11) 0.0357(10) 0.0487(12) 0.0177(9) 0.0184(10) 0.0206(9)
C18 0.0325(11) 0.0353(10) 0.0539(13) 0.0144(9) 0.0179(10) 0.0131(9)
_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
S1 C4 1.7201(15) . ?
S1 C2 1.7323(18) . ?
S2 O4 1.4197(13) . ?
S2 O3 1.4310(14) . ?
S2 N3 1.6423(15) . ?
S2 C13 1.7546(18) . ?
C1 C2 1.500(2) . ?
C1 H1A 0.89(2) . ?
C1 H1B 0.96(2) . ?
C1 H1C 1.02(2) . ?
C2 C3 1.340(2) . ?
C3 N1 1.386(2) . ?
C3 H3 0.975(18) . ?
C4 N1 1.3012(19) . ?
C4 N2 1.386(2) . ?
C5 O2 1.2388(18) . ?
C5 N2 1.358(2) . ?
C5 C6 1.458(2) . ?
C6 C7 1.357(2) . ?
C6 N3 1.4362(19) . ?
C7 O1 1.3412(18) . ?
C7 C8 1.470(2) . ?
C8 C9 1.389(2) . ?
C8 C13 1.399(2) . ?
C9 C10 1.385(3) . ?
C9 H9 0.965(16) . ?
C10 C11 1.377(3) . ?
C10 H10 0.95(2) . ?
C11 C12 1.381(3) . ?
C11 H11 0.97(2) . ?
C12 C13 1.391(2) . ?
C12 H12 0.932(18) . ?
C14 N3 1.484(3) . ?
C14 H14A 0.98(2) . ?
C14 H14B 0.90(2) . ?
C14 H14C 0.99(2) . ?
O1 H1 0.88(2) . ?
O5 C15 1.206(2) . ?
O6 C15 1.307(2) . ?
O6 H6 0.84(3) . ?
N2 H2 0.833(18) . ?
C15 C16 1.492(2) . ?
C16 C17 1.386(2) . ?
C16 C18 1.386(2) . ?
C17 C18 1.380(2) 2_656 ?
C17 H17 0.907(18) . ?
C18 C17 1.380(2) 2_656 ?
C18 H18 0.92(2) . ?
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
C4 S1 C2 88.97(8) . . ?
O4 S2 O3 119.80(9) . . ?
O4 S2 N3 108.10(8) . . ?
O3 S2 N3 107.51(8) . . ?
O4 S2 C13 108.86(8) . . ?
O3 S2 C13 109.53(9) . . ?
N3 S2 C13 101.47(8) . . ?
C2 C1 H1A 112.8(15) . . ?
C2 C1 H1B 111.1(12) . . ?
H1A C1 H1B 103.5(19) . . ?
C2 C1 H1C 110.9(13) . . ?
H1A C1 H1C 107.7(19) . . ?
H1B C1 H1C 110.5(19) . . ?
C3 C2 C1 127.98(17) . . ?
C3 C2 S1 109.60(12) . . ?
C1 C2 S1 122.28(14) . . ?
C2 C3 N1 116.20(16) . . ?
C2 C3 H3 126.3(10) . . ?
N1 C3 H3 117.5(10) . . ?
N1 C4 N2 120.63(14) . . ?
N1 C4 S1 115.37(12) . . ?
N2 C4 S1 123.93(12) . . ?
O2 C5 N2 121.59(15) . . ?
O2 C5 C6 121.76(15) . . ?
N2 C5 C6 116.65(14) . . ?
C7 C6 N3 120.87(14) . . ?
C7 C6 C5 121.17(14) . . ?
N3 C6 C5 117.90(14) . . ?
O1 C7 C6 123.55(15) . . ?
O1 C7 C8 114.45(14) . . ?
C6 C7 C8 122.00(14) . . ?
C9 C8 C13 118.44(16) . . ?
C9 C8 C7 121.43(16) . . ?
C13 C8 C7 120.10(14) . . ?
C10 C9 C8 120.44(18) . . ?
C10 C9 H9 122.1(10) . . ?
C8 C9 H9 117.3(10) . . ?
C11 C10 C9 120.36(19) . . ?
C11 C10 H10 123.3(12) . . ?
C9 C10 H10 116.4(12) . . ?
C10 C11 C12 120.60(19) . . ?
C10 C11 H11 121.2(11) . . ?
C12 C11 H11 118.2(11) . . ?
C11 C12 C13 119.00(19) . . ?
C11 C12 H12 122.6(11) . . ?
C13 C12 H12 118.4(11) . . ?
C12 C13 C8 121.16(17) . . ?
C12 C13 S2 122.11(14) . . ?
C8 C13 S2 116.71(12) . . ?
N3 C14 H14A 107.1(11) . . ?
N3 C14 H14B 109.3(13) . . ?
H14A C14 H14B 111.3(17) . . ?
N3 C14 H14C 110.5(13) . . ?
H14A C14 H14C 109.9(18) . . ?
H14B C14 H14C 108.7(17) . . ?
C7 O1 H1 101.1(13) . . ?
C15 O6 H6 110.0(18) . . ?
C4 N1 C3 109.82(13) . . ?
C5 N2 C4 124.27(14) . . ?
C5 N2 H2 119.9(13) . . ?
C4 N2 H2 115.7(13) . . ?
C6 N3 C14 114.41(16) . . ?
C6 N3 S2 112.54(11) . . ?
C14 N3 S2 117.05(12) . . ?
O5 C15 O6 122.92(16) . . ?
O5 C15 C16 122.79(16) . . ?
O6 C15 C16 114.30(15) . . ?
C17 C16 C18 119.39(15) . . ?
C17 C16 C15 121.83(15) . . ?
C18 C16 C15 118.75(16) . . ?
C18 C17 C16 120.53(16) 2_656 . ?
C18 C17 H17 119.2(12) 2_656 . ?
C16 C17 H17 120.3(12) . . ?
C17 C18 C16 120.08(17) 2_656 . ?
C17 C18 H18 119.7(11) 2_656 . ?
C16 C18 H18 120.2(11) . . ?
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
C4 S1 C2 C3 1.88(15) . . . . ?
C4 S1 C2 C1 -174.15(19) . . . . ?
C1 C2 C3 N1 174.0(2) . . . . ?
S1 C2 C3 N1 -1.7(2) . . . . ?
C2 S1 C4 N1 -1.81(15) . . . . ?
C2 S1 C4 N2 175.24(16) . . . . ?
O2 C5 C6 C7 -4.4(3) . . . . ?
N2 C5 C6 C7 174.59(16) . . . . ?
O2 C5 C6 N3 178.27(16) . . . . ?
N2 C5 C6 N3 -2.7(2) . . . . ?
N3 C6 C7 O1 177.72(15) . . . . ?
C5 C6 C7 O1 0.5(3) . . . . ?
N3 C6 C7 C8 -1.4(3) . . . . ?
C5 C6 C7 C8 -178.59(16) . . . . ?
O1 C7 C8 C9 25.8(2) . . . . ?
C6 C7 C8 C9 -154.99(17) . . . . ?
O1 C7 C8 C13 -156.34(16) . . . . ?
C6 C7 C8 C13 22.8(3) . . . . ?
C13 C8 C9 C10 -0.6(3) . . . . ?
C7 C8 C9 C10 177.25(17) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C10 C11 C12 -1.1(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C11 C12 C13 S2 -178.74(16) . . . . ?
C9 C8 C13 C12 0.2(3) . . . . ?
C7 C8 C13 C12 -177.67(17) . . . . ?
C9 C8 C13 S2 178.81(14) . . . . ?
C7 C8 C13 S2 0.9(2) . . . . ?
O4 S2 C13 C12 28.4(2) . . . . ?
O3 S2 C13 C12 -104.37(17) . . . . ?
N3 S2 C13 C12 142.20(16) . . . . ?
O4 S2 C13 C8 -150.22(14) . . . . ?
O3 S2 C13 C8 77.06(16) . . . . ?
N3 S2 C13 C8 -36.37(15) . . . . ?
N2 C4 N1 C3 -175.98(16) . . . . ?
S1 C4 N1 C3 1.2(2) . . . . ?
C2 C3 N1 C4 0.4(2) . . . . ?
O2 C5 N2 C4 6.7(3) . . . . ?
C6 C5 N2 C4 -172.38(16) . . . . ?
N1 C4 N2 C5 174.25(17) . . . . ?
S1 C4 N2 C5 -2.7(3) . . . . ?
C7 C6 N3 C14 95.3(2) . . . . ?
C5 C6 N3 C14 -87.44(19) . . . . ?
C7 C6 N3 S2 -41.6(2) . . . . ?
C5 C6 N3 S2 135.74(14) . . . . ?
O4 S2 N3 C6 169.72(11) . . . . ?
O3 S2 N3 C6 -59.64(13) . . . . ?
C13 S2 N3 C6 55.30(12) . . . . ?
O4 S2 N3 C14 34.13(15) . . . . ?
O3 S2 N3 C14 164.77(13) . . . . ?
C13 S2 N3 C14 -80.29(14) . . . . ?
O5 C15 C16 C17 -161.1(2) . . . . ?
O6 C15 C16 C17 19.0(3) . . . . ?
O5 C15 C16 C18 17.0(3) . . . . ?
O6 C15 C16 C18 -162.87(18) . . . . ?
C18 C16 C17 C18 0.0(3) . . . 2_656 ?
C15 C16 C17 C18 178.14(18) . . . 2_656 ?
C17 C16 C18 C17 0.0(3) . . . 2_656 ?
C15 C16 C18 C17 -178.20(18) . . . 2_656 ?
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
O1 H1 O2 0.88(2) 1.78(2) 2.6031(17) 155.4(18) .
N2 H2 O5 0.833(18) 2.183(19) 2.9841(19) 161.4(18) .
N2 H2 N3 0.833(18) 2.369(19) 2.7405(19) 107.8(15) .
O6 H6 N1 0.84(3) 1.80(3) 2.6388(18) 175(3) .
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 30.51
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 0.319
_refine_diff_density_min -0.301
_refine_diff_density_rms 0.048
_iucr_refine_instruction_details
;
TITL MEL_TEREPH IN P-1
CELL 0.71073 8.59791 10.45510 11.75150 91.35550 107.85600 109.44400
ZERR 2 0.00058 0.00059 0.00071 0.00470 0.00570 0.00560
LATT 1
SFAC C H N S O
UNIT 36 32 6 4 12
PLAN 30
SHEL 20 0.7
ACTA
CONF
FMAP 2
L.S. 20
ACTA
CONF
BOND $H
EQIV $1 1-X, 2-Y, 1-Z
HTAB O1 O2
HTAB O1 O2_$1
HTAB N2 O5
HTAB N2 N3
HTAB O6 N1
WGHT 0.042200
FVAR 2.63636
S1 4 0.811305 0.762189 0.226223 11.00000 0.04527 0.02750 =
0.04895 0.01443 0.02523 0.01942
S2 4 0.967191 0.186944 0.165823 11.00000 0.03788 0.02374 =
0.06273 0.00778 0.02262 0.01122
C1 1 0.564915 0.882395 0.237797 11.00000 0.06154 0.03730 =
0.06572 0.01624 0.03307 0.03268
H1A 2 0.641370 0.966075 0.271390 11.00000 0.06427
H1B 2 0.471524 0.872590 0.269210 11.00000 0.05963
H1C 2 0.522713 0.881926 0.146635 11.00000 0.08114
C2 1 0.640447 0.772548 0.269988 11.00000 0.04140 0.03098 =
0.03933 0.00703 0.01525 0.02070
C3 1 0.585118 0.665639 0.326751 11.00000 0.04013 0.03375 =
0.04007 0.00721 0.02009 0.01907
H3 2 0.491657 0.647553 0.361388 11.00000 0.03878
C4 1 0.788477 0.610135 0.284371 11.00000 0.03289 0.02373 =
0.03183 0.00643 0.01109 0.01262
C5 1 0.999331 0.555192 0.214259 11.00000 0.03275 0.02712 =
0.03659 0.00602 0.01361 0.01297
C6 1 1.069800 0.449001 0.200285 11.00000 0.03049 0.02413 =
0.03482 0.00744 0.01251 0.01188
C7 1 1.175968 0.461248 0.133086 11.00000 0.02958 0.02490 =
0.03291 0.00687 0.01022 0.00938
C8 1 1.245124 0.353950 0.115640 11.00000 0.03239 0.03349 =
0.02769 0.00494 0.01054 0.01481
C9 1 1.399116 0.383945 0.089175 11.00000 0.03767 0.04254 =
0.03503 0.00676 0.01625 0.01624
H9 2 1.460460 0.478489 0.084399 11.00000 0.03412
C10 1 1.465744 0.282330 0.078169 11.00000 0.04329 0.05978 =
0.04051 0.00615 0.01961 0.02742
H10 2 1.572168 0.309601 0.060954 11.00000 0.05077
C11 1 1.378560 0.149831 0.091440 11.00000 0.05590 0.05499 =
0.04776 0.00572 0.01954 0.03708
H11 2 1.421213 0.077188 0.080881 11.00000 0.05118
C12 1 1.225123 0.116701 0.117812 11.00000 0.05460 0.03422 =
0.05039 0.00529 0.02009 0.02354
H12 2 1.164250 0.028345 0.128785 11.00000 0.04087
C13 1 1.158857 0.218996 0.129588 11.00000 0.03677 0.03202 =
0.03989 0.00592 0.01478 0.01721
C14 1 1.127143 0.338591 0.382901 11.00000 0.04207 0.05317 =
0.04398 0.01997 0.01815 0.02535
H14A 2 1.128935 0.419723 0.426851 11.00000 0.04669
H14B 2 1.081057 0.262349 0.413133 11.00000 0.05048
H14C 2 1.248149 0.348106 0.388083 11.00000 0.07030
O1 5 1.224772 0.569634 0.076171 11.00000 0.04572 0.03173 =
0.05037 0.01766 0.02720 0.01778
H1 2 1.176509 0.622805 0.100060 11.00000 0.05532
O2 5 1.041664 0.663836 0.171794 11.00000 0.05311 0.02857 =
0.06046 0.01812 0.03366 0.02073
O3 5 0.826354 0.181895 0.059933 11.00000 0.03577 0.04381 =
0.06692 -0.00804 0.00567 0.01105
O4 5 0.947781 0.076617 0.234853 11.00000 0.06825 0.03027 =
0.10374 0.02821 0.05304 0.02259
O5 5 0.785913 0.308913 0.425179 11.00000 0.04987 0.05646 =
0.13281 0.05620 0.05584 0.03034
O6 5 0.534311 0.333945 0.405465 11.00000 0.04712 0.03834 =
0.07987 0.03118 0.03852 0.02489
H6 2 0.580998 0.407601 0.381329 11.00000 0.09815
N1 3 0.668604 0.571641 0.335171 11.00000 0.03821 0.02880 =
0.03632 0.00991 0.01718 0.01624
N2 3 0.882835 0.528198 0.274632 11.00000 0.03821 0.02523 =
0.04275 0.01169 0.01943 0.01690
H2 2 0.859492 0.455888 0.304836 11.00000 0.04604
N3 3 1.017146 0.328029 0.255462 11.00000 0.03647 0.02660 =
0.04081 0.01236 0.01851 0.01661
C15 1 0.640176 0.265462 0.430806 11.00000 0.04141 0.03438 =
0.04730 0.01549 0.02403 0.01762
C16 1 0.565576 0.128905 0.467565 11.00000 0.03582 0.02665 =
0.03973 0.00996 0.01847 0.01280
C17 1 0.387020 0.063512 0.441194 11.00000 0.03970 0.03571 =
0.04871 0.01772 0.01841 0.02063
H17 2 0.311585 0.103611 0.401035 11.00000 0.04202
C18 1 0.678478 0.064497 0.526685 11.00000 0.03249 0.03532 =
0.05392 0.01436 0.01789 0.01305
H18 2 0.797642 0.108108 0.546864 11.00000 0.04976
HKLF 4
REM MEL_TEREPH IN P-1
REM R1 = 0.0432 for 3365 Fo > 4sig(Fo) and 0.0896 for all 5721 data
REM 326 parameters refined using 0 restraints
END
WGHT 0.0422 0.0000
REM Highest difference peak 0.319, deepest hole -0.301, 1-sigma level 0.048
Q1 1 0.8003 0.6815 0.2669 11.00000 0.05 0.32
Q2 1 1.0683 0.1967 0.1440 11.00000 0.05 0.32
Q3 1 0.4357 0.8401 0.1373 11.00000 0.05 0.24
Q4 1 1.3147 0.3759 0.1027 11.00000 0.05 0.23
Q5 1 1.0827 0.4236 0.1317 11.00000 0.05 0.23
Q6 1 0.6953 0.2785 0.3751 11.00000 0.05 0.22
Q7 1 1.2128 0.4060 0.1183 11.00000 0.05 0.22
Q8 1 0.5726 0.8029 0.2515 11.00000 0.05 0.22
Q9 1 1.0369 0.4941 0.2078 11.00000 0.05 0.21
Q10 1 1.1630 0.4792 0.1975 11.00000 0.05 0.21
Q11 1 0.7605 0.3402 0.4746 11.00000 0.05 0.20
Q12 1 0.7158 0.7793 0.2406 11.00000 0.05 0.20
Q13 1 1.4313 0.3281 0.0733 11.00000 0.05 0.19
Q14 1 0.6262 0.6175 0.3301 11.00000 0.05 0.19
Q15 1 0.6431 0.9573 0.2095 11.00000 0.05 0.19
Q16 1 0.9454 0.5438 0.2451 11.00000 0.05 0.19
Q17 1 0.7852 0.1732 0.0063 11.00000 0.05 0.19
Q18 1 1.0559 0.3353 0.2998 11.00000 0.05 0.19
Q19 1 1.1806 0.5003 0.1098 11.00000 0.05 0.19
Q20 1 0.5821 0.1781 0.4185 11.00000 0.05 0.19
Q21 1 0.8843 0.1577 0.0737 11.00000 0.05 0.18
Q22 1 0.6451 0.4967 0.3529 11.00000 0.05 0.18
Q23 1 1.1943 0.1775 0.1204 11.00000 0.05 0.18
Q24 1 1.2240 0.2793 0.1440 11.00000 0.05 0.18
Q25 1 0.6321 0.1166 0.5372 11.00000 0.05 0.18
Q26 1 0.5596 0.6787 0.3609 11.00000 0.05 0.18
Q27 1 0.4807 0.0909 0.4294 11.00000 0.05 0.18
Q28 1 0.9650 0.1483 0.2267 11.00000 0.05 0.18
Q29 1 0.8219 0.5654 0.2640 11.00000 0.05 0.17
Q30 1 1.0214 0.2644 0.2482 11.00000 0.05 0.17
;