Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113009487/ky3031sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113009487/ky3031Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113009487/ky3031IIsup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113009487/ky3031Isup4.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113009487/ky3031IIsup5.cml |
CCDC references: 950371; 950372
For related literature, see: Arman et al. (2010); Bettinetti & Sardone (1997); Caira (1991, 1992, 2007); Etter et al. (1990); Ghosh et al. (2011); Kumar et al. (2003); Lu et al. (2008, 2011); Lucaciu et al. (2008); Lynch et al. (2000); O'Neil (2001); Patel et al. (1988); Rambaud et al. (1985); Sardone et al. (1997); Smith & Wermuth (2012, 2013a, 2013b); Smith et al. (1996, 2005, 2006, 2007); Spek (2009); Tiwari et al. (1984).
The title salts, (I) and (II), were prepared by the reaction of 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (sulfamethazine; 1 mmol, 280 mg) with, respectively, 5-nitrosalicylic acid (1 mmol, 180 mg) or picric acid (1 mmol, 230 mg) in 50% ethanol–water (50 ml) under reflux for 10 min. Partial evaporation of the solvent gave colourless plates of (I) (m.p. 478–479 K) or yellow blocks of (II) (m.p. 469–471 K), from which specimens were cleaved for the X-ray analyses.
H atoms potentially involved in hydrogen-bonding interactions were located by difference methods, and their positional and isotropic displacement parameters were refined. In (I), the N1A—H1A distance was restrained to 0.88 (2) Å. All other H atoms were included at calculated positions [aromatic C—H = 0.95 Å or methyl C—H = 0.98 Å] and treated as riding, with Uiso(H) = 1.2Ueq(C) for aromatic or 1.5Ueq(C) for methyl H atoms. With (I), in the absence of any indication of twinning [`no twin law detected', TwinRotMat (PLATON, Spek, 2009)], the pseudo-orthorhombic P21/n unit cell was accepted. For (II), the H atoms of one of the methyl groups (C42A) were rotationally disordered over six half-sites and were treated accordingly in the refinement [Final site occupancies?].
For both compounds, data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).
C12H15N4O2S+·C7H4NO5− | F(000) = 1920 |
Mr = 461.46 | Dx = 1.493 Mg m−3 |
Monoclinic, P21/n | Melting point = 478–479 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1611 (2) Å | Cell parameters from 13808 reflections |
b = 14.0977 (2) Å | θ = 3.2–28.7° |
c = 22.1219 (3) Å | µ = 0.21 mm−1 |
β = 90.094 (2)° | T = 200 K |
V = 4104.52 (10) Å3 | Plate, colourless |
Z = 8 | 0.35 × 0.35 × 0.15 mm |
Oxford Gemini-S Ultra CCD area-detector diffractometer | 8057 independent reflections |
Radiation source: Enhance (Mo) X-ray source | 5991 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ω scans | θmax = 26.0°, θmin = 3.3° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | h = −16→16 |
Tmin = 0.960, Tmax = 0.980 | k = −17→17 |
30179 measured reflections | l = −27→27 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0571P)2] where P = (Fo2 + 2Fc2)/3 |
8057 reflections | (Δ/σ)max = 0.007 |
621 parameters | Δρmax = 0.28 e Å−3 |
1 restraint | Δρmin = −0.30 e Å−3 |
C12H15N4O2S+·C7H4NO5− | V = 4104.52 (10) Å3 |
Mr = 461.46 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.1611 (2) Å | µ = 0.21 mm−1 |
b = 14.0977 (2) Å | T = 200 K |
c = 22.1219 (3) Å | 0.35 × 0.35 × 0.15 mm |
β = 90.094 (2)° |
Oxford Gemini-S Ultra CCD area-detector diffractometer | 8057 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 5991 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.980 | Rint = 0.025 |
30179 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 1 restraint |
wR(F2) = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.28 e Å−3 |
8057 reflections | Δρmin = −0.30 e Å−3 |
621 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1A | 0.07153 (3) | 0.67064 (3) | 0.69347 (2) | 0.0288 (1) | |
O11A | −0.02458 (8) | 0.62533 (8) | 0.70202 (5) | 0.0372 (4) | |
O12A | 0.08020 (9) | 0.77122 (8) | 0.70003 (5) | 0.0387 (4) | |
N1A | 0.12334 (9) | 0.56980 (9) | 0.53296 (6) | 0.0223 (4) | |
N2A | 0.10773 (10) | 0.65526 (10) | 0.62149 (6) | 0.0268 (4) | |
N3A | 0.10208 (9) | 0.49098 (9) | 0.62605 (6) | 0.0261 (4) | |
N41A | 0.37418 (14) | 0.48612 (14) | 0.85115 (8) | 0.0476 (7) | |
C2A | 0.11060 (11) | 0.56942 (10) | 0.59352 (7) | 0.0219 (4) | |
C4A | 0.10701 (11) | 0.40782 (10) | 0.59619 (7) | 0.0269 (5) | |
C5A | 0.11914 (11) | 0.40380 (11) | 0.53373 (7) | 0.0265 (5) | |
C6A | 0.12785 (10) | 0.48715 (10) | 0.50191 (7) | 0.0231 (4) | |
C11A | 0.16171 (12) | 0.61476 (11) | 0.73886 (7) | 0.0273 (5) | |
C21A | 0.25203 (13) | 0.66125 (11) | 0.75263 (7) | 0.0301 (5) | |
C31A | 0.32363 (13) | 0.61707 (12) | 0.78855 (7) | 0.0320 (5) | |
C41A | 0.30519 (13) | 0.52674 (11) | 0.81264 (7) | 0.0315 (5) | |
C42A | 0.09958 (15) | 0.32077 (12) | 0.63395 (8) | 0.0409 (6) | |
C51A | 0.21385 (13) | 0.48115 (11) | 0.79852 (7) | 0.0331 (6) | |
C61A | 0.14306 (12) | 0.52406 (11) | 0.76199 (7) | 0.0295 (5) | |
C62A | 0.14456 (12) | 0.49267 (11) | 0.43539 (7) | 0.0293 (5) | |
S1B | 0.92340 (3) | 0.25241 (3) | 0.79543 (2) | 0.0281 (1) | |
O11B | 1.01786 (8) | 0.29519 (8) | 0.77910 (5) | 0.0375 (4) | |
O12B | 0.91201 (9) | 0.15187 (8) | 0.78933 (5) | 0.0381 (4) | |
N1B | 0.87859 (9) | 0.35527 (10) | 0.95621 (6) | 0.0241 (4) | |
N2B | 0.90467 (10) | 0.26742 (10) | 0.86958 (6) | 0.0283 (4) | |
N3B | 0.91195 (10) | 0.43170 (9) | 0.86353 (6) | 0.0266 (4) | |
N41B | 0.58517 (14) | 0.44107 (13) | 0.66992 (9) | 0.0504 (7) | |
C2B | 0.89904 (11) | 0.35379 (10) | 0.89624 (7) | 0.0233 (5) | |
C4B | 0.90126 (11) | 0.51537 (11) | 0.89198 (7) | 0.0270 (5) | |
C5B | 0.88147 (12) | 0.52088 (11) | 0.95369 (7) | 0.0286 (5) | |
C6B | 0.86996 (11) | 0.43832 (11) | 0.98618 (7) | 0.0251 (5) | |
C11B | 0.82365 (11) | 0.31070 (11) | 0.75987 (7) | 0.0245 (5) | |
C21B | 0.72877 (12) | 0.26729 (11) | 0.75756 (7) | 0.0283 (5) | |
C31B | 0.65008 (12) | 0.31123 (11) | 0.72858 (7) | 0.0299 (5) | |
C41B | 0.66316 (12) | 0.39982 (11) | 0.70119 (7) | 0.0299 (5) | |
C42B | 0.91208 (14) | 0.60161 (11) | 0.85326 (8) | 0.0369 (6) | |
C51B | 0.75855 (12) | 0.44401 (11) | 0.70520 (7) | 0.0299 (5) | |
C61B | 0.83785 (12) | 0.39970 (11) | 0.73375 (7) | 0.0272 (5) | |
C62B | 0.84715 (13) | 0.43421 (12) | 1.05216 (8) | 0.0346 (6) | |
O2C | 0.86063 (10) | 0.12638 (9) | 1.12344 (6) | 0.0409 (4) | |
O11C | 0.87460 (9) | 0.10804 (8) | 0.93667 (5) | 0.0349 (4) | |
O12C | 0.86850 (10) | 0.19851 (8) | 1.01921 (5) | 0.0407 (4) | |
O51C | 0.88240 (11) | −0.29921 (9) | 1.05247 (7) | 0.0568 (5) | |
O52C | 0.88819 (14) | −0.23713 (10) | 0.96357 (7) | 0.0721 (7) | |
N5C | 0.88198 (11) | −0.23014 (10) | 1.01871 (8) | 0.0408 (6) | |
C1C | 0.87128 (11) | 0.03235 (11) | 1.03253 (7) | 0.0249 (5) | |
C2C | 0.86472 (11) | 0.04133 (11) | 1.09589 (7) | 0.0273 (5) | |
C3C | 0.86229 (12) | −0.03944 (12) | 1.13268 (8) | 0.0330 (5) | |
C4C | 0.86768 (12) | −0.12790 (12) | 1.10761 (8) | 0.0321 (5) | |
C5C | 0.87478 (11) | −0.13593 (11) | 1.04502 (8) | 0.0285 (5) | |
C6C | 0.87714 (11) | −0.05767 (11) | 1.00755 (7) | 0.0271 (5) | |
C11C | 0.87166 (11) | 0.11811 (11) | 0.99236 (7) | 0.0274 (5) | |
O2D | 0.14667 (11) | 0.79122 (9) | 0.36510 (6) | 0.0483 (5) | |
O11D | 0.11640 (9) | 0.81801 (8) | 0.55065 (5) | 0.0357 (4) | |
O12D | 0.13518 (10) | 0.72445 (8) | 0.47061 (5) | 0.0425 (4) | |
O51D | 0.12968 (12) | 1.22050 (9) | 0.42635 (7) | 0.0572 (5) | |
O52D | 0.11007 (10) | 1.16310 (8) | 0.51618 (6) | 0.0442 (5) | |
N5D | 0.12073 (10) | 1.15325 (10) | 0.46110 (7) | 0.0348 (5) | |
C1D | 0.12832 (11) | 0.88941 (11) | 0.45319 (7) | 0.0246 (5) | |
C2D | 0.13815 (12) | 0.87685 (11) | 0.39024 (7) | 0.0293 (5) | |
C3D | 0.14014 (13) | 0.95564 (12) | 0.35148 (8) | 0.0358 (6) | |
C4D | 0.13393 (12) | 1.04569 (12) | 0.37452 (8) | 0.0322 (5) | |
C5D | 0.12471 (11) | 1.05756 (11) | 0.43673 (7) | 0.0261 (5) | |
C6D | 0.12100 (11) | 0.98103 (10) | 0.47596 (7) | 0.0248 (5) | |
C11D | 0.12604 (12) | 0.80620 (11) | 0.49551 (7) | 0.0272 (5) | |
H1A | 0.1296 (15) | 0.6270 (12) | 0.5115 (9) | 0.066 (7)* | |
H2A | 0.1125 (14) | 0.7051 (14) | 0.6004 (9) | 0.050 (6)* | |
H5A | 0.12140 | 0.34440 | 0.51340 | 0.0320* | |
H21A | 0.26440 | 0.72320 | 0.73740 | 0.0360* | |
H31A | 0.38610 | 0.64820 | 0.79700 | 0.0380* | |
H41A | 0.3718 (17) | 0.4292 (18) | 0.8578 (11) | 0.076 (9)* | |
H42A | 0.4348 (18) | 0.5140 (15) | 0.8518 (10) | 0.066 (7)* | |
H43A | 0.10930 | 0.26470 | 0.60840 | 0.0610* | |
H44A | 0.03240 | 0.31800 | 0.65290 | 0.0610* | |
H45A | 0.15210 | 0.32230 | 0.66540 | 0.0610* | |
H51A | 0.20060 | 0.41980 | 0.81440 | 0.0400* | |
H61A | 0.08150 | 0.49220 | 0.75240 | 0.0350* | |
H63A | 0.21500 | 0.51120 | 0.42740 | 0.0440* | |
H64A | 0.09840 | 0.53990 | 0.41790 | 0.0440* | |
H65A | 0.13120 | 0.43060 | 0.41710 | 0.0440* | |
H1B | 0.8742 (14) | 0.2998 (14) | 0.9766 (9) | 0.050 (6)* | |
H2B | 0.8939 (13) | 0.2133 (13) | 0.8892 (9) | 0.041 (5)* | |
H5B | 0.87600 | 0.58080 | 0.97310 | 0.0340* | |
H21B | 0.71870 | 0.20720 | 0.77610 | 0.0340* | |
H31B | 0.58550 | 0.28120 | 0.72700 | 0.0360* | |
H41B | 0.5276 (18) | 0.4084 (16) | 0.6715 (11) | 0.076 (8)* | |
H42B | 0.5908 (15) | 0.4978 (15) | 0.6598 (9) | 0.052 (6)* | |
H43B | 0.86600 | 0.59680 | 0.81850 | 0.0550* | |
H44B | 0.98230 | 0.60640 | 0.83890 | 0.0550* | |
H45B | 0.89500 | 0.65820 | 0.87690 | 0.0550* | |
H51B | 0.76820 | 0.50510 | 0.68800 | 0.0360* | |
H61B | 0.90250 | 0.42960 | 0.73580 | 0.0330* | |
H63B | 0.85550 | 0.49740 | 1.06990 | 0.0520* | |
H64B | 0.89390 | 0.38980 | 1.07190 | 0.0520* | |
H65B | 0.77700 | 0.41270 | 1.05810 | 0.0520* | |
H2C | 0.8596 (18) | 0.1687 (18) | 1.0934 (12) | 0.088 (9)* | |
H3C | 0.85690 | −0.03270 | 1.17530 | 0.0400* | |
H4C | 0.86660 | −0.18290 | 1.13240 | 0.0380* | |
H6C | 0.88270 | −0.06540 | 0.96500 | 0.0320* | |
H2D | 0.1502 (17) | 0.7500 (15) | 0.3961 (11) | 0.069 (7)* | |
H3D | 0.14580 | 0.94650 | 0.30910 | 0.0430* | |
H4D | 0.13590 | 1.09920 | 0.34840 | 0.0390* | |
H6D | 0.11350 | 0.99110 | 0.51820 | 0.0300* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0366 (2) | 0.0253 (2) | 0.0246 (2) | 0.0057 (2) | 0.0043 (2) | −0.0012 (2) |
O11A | 0.0326 (6) | 0.0433 (7) | 0.0358 (7) | 0.0063 (5) | 0.0071 (5) | 0.0024 (6) |
O12A | 0.0566 (8) | 0.0255 (6) | 0.0340 (7) | 0.0101 (5) | 0.0032 (6) | −0.0046 (5) |
N1A | 0.0231 (7) | 0.0198 (7) | 0.0239 (7) | 0.0007 (5) | −0.0004 (5) | 0.0017 (6) |
N2A | 0.0393 (8) | 0.0188 (7) | 0.0222 (7) | 0.0012 (6) | 0.0028 (6) | 0.0017 (6) |
N3A | 0.0305 (7) | 0.0219 (7) | 0.0258 (7) | −0.0005 (5) | 0.0009 (6) | 0.0015 (6) |
N41A | 0.0518 (11) | 0.0364 (11) | 0.0544 (12) | −0.0002 (9) | −0.0185 (9) | 0.0039 (8) |
C2A | 0.0210 (7) | 0.0223 (8) | 0.0225 (8) | 0.0016 (6) | 0.0000 (6) | 0.0016 (6) |
C4A | 0.0271 (8) | 0.0218 (8) | 0.0318 (9) | −0.0009 (6) | −0.0002 (7) | 0.0009 (7) |
C5A | 0.0279 (8) | 0.0195 (8) | 0.0322 (9) | −0.0002 (6) | −0.0006 (7) | −0.0047 (7) |
C6A | 0.0192 (7) | 0.0243 (8) | 0.0257 (8) | 0.0014 (6) | −0.0023 (6) | −0.0016 (7) |
C11A | 0.0359 (9) | 0.0255 (9) | 0.0204 (8) | 0.0006 (7) | 0.0038 (7) | −0.0027 (7) |
C21A | 0.0445 (10) | 0.0230 (8) | 0.0227 (8) | −0.0031 (7) | 0.0033 (7) | −0.0025 (7) |
C31A | 0.0370 (9) | 0.0297 (9) | 0.0293 (9) | −0.0040 (7) | −0.0007 (7) | −0.0073 (7) |
C41A | 0.0412 (10) | 0.0273 (9) | 0.0259 (9) | 0.0047 (7) | −0.0015 (7) | −0.0054 (7) |
C42A | 0.0611 (12) | 0.0245 (9) | 0.0370 (10) | −0.0028 (8) | 0.0039 (9) | 0.0050 (8) |
C51A | 0.0459 (10) | 0.0230 (9) | 0.0304 (10) | −0.0024 (7) | 0.0004 (8) | 0.0026 (7) |
C61A | 0.0353 (9) | 0.0266 (9) | 0.0265 (9) | −0.0050 (7) | 0.0022 (7) | −0.0009 (7) |
C62A | 0.0324 (9) | 0.0300 (9) | 0.0255 (9) | 0.0030 (7) | −0.0019 (7) | −0.0026 (7) |
S1B | 0.0368 (2) | 0.0250 (2) | 0.0224 (2) | 0.0059 (2) | 0.0015 (2) | −0.0006 (2) |
O11B | 0.0336 (6) | 0.0452 (7) | 0.0338 (7) | 0.0075 (5) | 0.0063 (5) | 0.0026 (6) |
O12B | 0.0594 (8) | 0.0246 (6) | 0.0304 (7) | 0.0115 (5) | −0.0033 (6) | −0.0038 (5) |
N1B | 0.0285 (7) | 0.0221 (7) | 0.0218 (7) | 0.0000 (5) | −0.0007 (5) | 0.0017 (6) |
N2B | 0.0444 (8) | 0.0196 (7) | 0.0209 (7) | 0.0023 (6) | −0.0004 (6) | 0.0021 (6) |
N3B | 0.0318 (7) | 0.0234 (7) | 0.0247 (7) | 0.0012 (5) | 0.0000 (6) | 0.0013 (6) |
N41B | 0.0495 (11) | 0.0296 (10) | 0.0719 (13) | −0.0001 (8) | −0.0258 (9) | 0.0056 (9) |
C2B | 0.0251 (8) | 0.0232 (8) | 0.0215 (8) | 0.0013 (6) | −0.0016 (6) | 0.0013 (6) |
C4B | 0.0270 (8) | 0.0239 (9) | 0.0302 (9) | 0.0001 (6) | −0.0010 (7) | 0.0023 (7) |
C5B | 0.0335 (9) | 0.0245 (9) | 0.0278 (9) | −0.0005 (7) | 0.0016 (7) | −0.0040 (7) |
C6B | 0.0228 (8) | 0.0272 (9) | 0.0252 (9) | −0.0010 (6) | −0.0011 (6) | −0.0016 (7) |
C11B | 0.0330 (9) | 0.0236 (8) | 0.0168 (8) | 0.0008 (6) | 0.0013 (6) | −0.0018 (6) |
C21B | 0.0412 (10) | 0.0213 (8) | 0.0224 (8) | −0.0014 (7) | 0.0038 (7) | 0.0004 (7) |
C31B | 0.0322 (9) | 0.0254 (9) | 0.0322 (9) | −0.0033 (7) | −0.0001 (7) | −0.0048 (7) |
C41B | 0.0374 (9) | 0.0250 (9) | 0.0274 (9) | 0.0033 (7) | −0.0054 (7) | −0.0043 (7) |
C42B | 0.0520 (11) | 0.0261 (9) | 0.0327 (10) | 0.0004 (8) | 0.0047 (8) | 0.0043 (8) |
C51B | 0.0443 (10) | 0.0217 (8) | 0.0236 (9) | −0.0025 (7) | −0.0012 (7) | 0.0027 (7) |
C61B | 0.0325 (9) | 0.0260 (9) | 0.0232 (8) | −0.0030 (7) | 0.0018 (7) | −0.0001 (7) |
C62B | 0.0421 (10) | 0.0339 (10) | 0.0279 (9) | −0.0030 (8) | 0.0045 (8) | −0.0037 (8) |
O2C | 0.0644 (9) | 0.0274 (7) | 0.0310 (7) | −0.0040 (6) | 0.0002 (6) | 0.0009 (6) |
O11C | 0.0451 (7) | 0.0326 (7) | 0.0269 (7) | −0.0026 (5) | −0.0013 (5) | 0.0059 (5) |
O12C | 0.0668 (9) | 0.0249 (7) | 0.0304 (7) | −0.0046 (6) | −0.0010 (6) | 0.0051 (5) |
O51C | 0.0772 (10) | 0.0245 (7) | 0.0686 (10) | 0.0024 (6) | −0.0139 (8) | 0.0057 (7) |
O52C | 0.1214 (15) | 0.0410 (9) | 0.0538 (10) | 0.0047 (8) | 0.0094 (10) | −0.0133 (8) |
N5C | 0.0386 (9) | 0.0293 (9) | 0.0545 (11) | 0.0021 (7) | −0.0038 (7) | −0.0036 (8) |
C1C | 0.0192 (7) | 0.0252 (8) | 0.0303 (9) | −0.0020 (6) | −0.0025 (6) | 0.0049 (7) |
C2C | 0.0273 (8) | 0.0243 (9) | 0.0303 (9) | −0.0034 (7) | −0.0013 (7) | 0.0002 (7) |
C3C | 0.0374 (9) | 0.0339 (10) | 0.0277 (9) | −0.0038 (8) | −0.0007 (7) | 0.0058 (8) |
C4C | 0.0267 (9) | 0.0280 (9) | 0.0415 (10) | −0.0022 (7) | −0.0015 (7) | 0.0101 (8) |
C5C | 0.0203 (8) | 0.0248 (9) | 0.0404 (10) | 0.0005 (6) | −0.0012 (7) | 0.0011 (7) |
C6C | 0.0210 (8) | 0.0312 (9) | 0.0290 (9) | 0.0002 (6) | −0.0004 (6) | −0.0013 (7) |
C11C | 0.0239 (8) | 0.0279 (9) | 0.0303 (9) | −0.0033 (7) | −0.0020 (7) | 0.0051 (7) |
O2D | 0.0902 (11) | 0.0265 (7) | 0.0283 (7) | −0.0028 (7) | 0.0147 (7) | −0.0059 (6) |
O11D | 0.0570 (8) | 0.0265 (6) | 0.0235 (6) | 0.0013 (5) | 0.0009 (5) | 0.0034 (5) |
O12D | 0.0757 (9) | 0.0197 (6) | 0.0320 (7) | 0.0045 (6) | 0.0147 (6) | 0.0019 (5) |
O51D | 0.0918 (11) | 0.0228 (7) | 0.0570 (9) | −0.0029 (7) | 0.0057 (8) | 0.0089 (7) |
O52D | 0.0656 (9) | 0.0297 (7) | 0.0373 (8) | 0.0035 (6) | −0.0029 (6) | −0.0090 (6) |
N5D | 0.0378 (8) | 0.0219 (8) | 0.0448 (10) | −0.0005 (6) | −0.0030 (7) | 0.0012 (7) |
C1D | 0.0268 (8) | 0.0224 (8) | 0.0246 (8) | −0.0019 (6) | 0.0023 (6) | 0.0013 (7) |
C2D | 0.0374 (9) | 0.0232 (9) | 0.0272 (9) | −0.0029 (7) | 0.0065 (7) | −0.0016 (7) |
C3D | 0.0490 (11) | 0.0353 (10) | 0.0230 (9) | −0.0057 (8) | 0.0060 (8) | 0.0024 (7) |
C4D | 0.0377 (9) | 0.0270 (9) | 0.0318 (10) | −0.0042 (7) | 0.0011 (7) | 0.0084 (7) |
C5D | 0.0261 (8) | 0.0211 (8) | 0.0311 (9) | −0.0018 (6) | −0.0009 (7) | 0.0011 (7) |
C6D | 0.0260 (8) | 0.0253 (8) | 0.0232 (8) | 0.0000 (6) | 0.0013 (6) | −0.0008 (7) |
C11D | 0.0302 (9) | 0.0237 (9) | 0.0278 (9) | 0.0009 (7) | 0.0032 (7) | 0.0019 (7) |
S1A—O11A | 1.4299 (11) | C5A—H5A | 0.9500 |
S1A—O12A | 1.4299 (12) | C21A—H21A | 0.9500 |
S1A—N2A | 1.6770 (14) | C31A—H31A | 0.9500 |
S1A—C11A | 1.7417 (16) | C42A—H45A | 0.9800 |
S1B—O11B | 1.4287 (11) | C42A—H43A | 0.9800 |
S1B—O12B | 1.4316 (12) | C42A—H44A | 0.9800 |
S1B—N2B | 1.6726 (14) | C51A—H51A | 0.9500 |
S1B—C11B | 1.7362 (15) | C61A—H61A | 0.9500 |
O2C—C2C | 1.346 (2) | C62A—H65A | 0.9800 |
O11C—C11C | 1.2408 (19) | C62A—H63A | 0.9800 |
O12C—C11C | 1.2804 (19) | C62A—H64A | 0.9800 |
O51C—N5C | 1.227 (2) | C4B—C5B | 1.392 (2) |
O52C—N5C | 1.227 (2) | C4B—C42B | 1.494 (2) |
O2C—H2C | 0.89 (3) | C5B—C6B | 1.376 (2) |
O2D—C2D | 1.334 (2) | C6B—C62B | 1.492 (2) |
O11D—C11D | 1.2378 (19) | C11B—C21B | 1.392 (2) |
O12D—C11D | 1.2831 (19) | C11B—C61B | 1.394 (2) |
O51D—N5D | 1.226 (2) | C21B—C31B | 1.366 (2) |
O52D—N5D | 1.235 (2) | C31B—C41B | 1.399 (2) |
O2D—H2D | 0.90 (2) | C41B—C51B | 1.404 (2) |
N1A—C2A | 1.350 (2) | C51B—C61B | 1.370 (2) |
N1A—C6A | 1.3539 (19) | C5B—H5B | 0.9500 |
N2A—C2A | 1.360 (2) | C21B—H21B | 0.9500 |
N3A—C4A | 1.3473 (19) | C31B—H31B | 0.9500 |
N3A—C2A | 1.3242 (19) | C42B—H45B | 0.9800 |
N41A—C41A | 1.370 (2) | C42B—H44B | 0.9800 |
N1A—H1A | 0.939 (18) | C42B—H43B | 0.9800 |
N2A—H2A | 0.85 (2) | C51B—H51B | 0.9500 |
N41A—H41A | 0.82 (3) | C61B—H61B | 0.9500 |
N41A—H42A | 0.89 (2) | C62B—H65B | 0.9800 |
N1B—C6B | 1.350 (2) | C62B—H63B | 0.9800 |
N1B—C2B | 1.354 (2) | C62B—H64B | 0.9800 |
N2B—C2B | 1.355 (2) | C1C—C11C | 1.501 (2) |
N3B—C2B | 1.3264 (19) | C1C—C6C | 1.386 (2) |
N3B—C4B | 1.344 (2) | C1C—C2C | 1.410 (2) |
N41B—C41B | 1.367 (2) | C2C—C3C | 1.400 (2) |
N1B—H1B | 0.91 (2) | C3C—C4C | 1.367 (2) |
N2B—H2B | 0.889 (19) | C4C—C5C | 1.393 (3) |
N41B—H41B | 0.89 (2) | C5C—C6C | 1.380 (2) |
N41B—H42B | 0.83 (2) | C3C—H3C | 0.9500 |
N5C—C5C | 1.453 (2) | C4C—H4C | 0.9500 |
N5D—C5D | 1.454 (2) | C6C—H6C | 0.9500 |
C4A—C5A | 1.392 (2) | C1D—C6D | 1.390 (2) |
C4A—C42A | 1.488 (2) | C1D—C11D | 1.501 (2) |
C5A—C6A | 1.375 (2) | C1D—C2D | 1.410 (2) |
C6A—C62A | 1.490 (2) | C2D—C3D | 1.404 (2) |
C11A—C21A | 1.391 (2) | C3D—C4D | 1.371 (2) |
C11A—C61A | 1.399 (2) | C4D—C5D | 1.392 (2) |
C21A—C31A | 1.380 (2) | C5D—C6D | 1.386 (2) |
C31A—C41A | 1.402 (2) | C3D—H3D | 0.9500 |
C41A—C51A | 1.398 (2) | C4D—H4D | 0.9500 |
C51A—C61A | 1.373 (2) | C6D—H6D | 0.9500 |
O11A—S1A—O12A | 120.00 (7) | N1B—C2B—N2B | 116.83 (13) |
O11A—S1A—N2A | 108.70 (7) | N1B—C2B—N3B | 123.20 (14) |
O11A—S1A—C11A | 108.90 (7) | N3B—C4B—C42B | 115.81 (14) |
O12A—S1A—N2A | 101.64 (7) | C5B—C4B—C42B | 122.33 (14) |
O12A—S1A—C11A | 109.63 (7) | N3B—C4B—C5B | 121.86 (14) |
N2A—S1A—C11A | 107.13 (7) | C4B—C5B—C6B | 119.06 (14) |
O11B—S1B—N2B | 108.92 (7) | N1B—C6B—C5B | 117.86 (14) |
O11B—S1B—C11B | 110.08 (7) | C5B—C6B—C62B | 124.49 (14) |
O12B—S1B—N2B | 101.66 (7) | N1B—C6B—C62B | 117.64 (14) |
O12B—S1B—C11B | 110.30 (7) | S1B—C11B—C21B | 119.10 (12) |
N2B—S1B—C11B | 105.78 (7) | S1B—C11B—C61B | 120.80 (12) |
O11B—S1B—O12B | 119.02 (7) | C21B—C11B—C61B | 120.10 (14) |
C2C—O2C—H2C | 105.0 (17) | C11B—C21B—C31B | 119.84 (14) |
C2D—O2D—H2D | 105.7 (14) | C21B—C31B—C41B | 120.97 (15) |
C2A—N1A—C6A | 120.37 (13) | C31B—C41B—C51B | 118.65 (14) |
S1A—N2A—C2A | 123.73 (11) | N41B—C41B—C51B | 120.92 (15) |
C2A—N3A—C4A | 117.13 (13) | N41B—C41B—C31B | 120.41 (15) |
C6A—N1A—H1A | 118.6 (12) | C41B—C51B—C61B | 120.48 (14) |
C2A—N1A—H1A | 121.1 (12) | C11B—C61B—C51B | 119.93 (14) |
S1A—N2A—H2A | 116.0 (13) | C4B—C5B—H5B | 120.00 |
C2A—N2A—H2A | 119.1 (14) | C6B—C5B—H5B | 120.00 |
C41A—N41A—H41A | 119.8 (16) | C31B—C21B—H21B | 120.00 |
H41A—N41A—H42A | 118 (2) | C11B—C21B—H21B | 120.00 |
C41A—N41A—H42A | 114.8 (14) | C21B—C31B—H31B | 120.00 |
C2B—N1B—C6B | 120.75 (14) | C41B—C31B—H31B | 120.00 |
S1B—N2B—C2B | 123.29 (11) | C4B—C42B—H43B | 109.00 |
C2B—N3B—C4B | 117.23 (13) | C4B—C42B—H44B | 109.00 |
C6B—N1B—H1B | 120.0 (13) | H43B—C42B—H44B | 109.00 |
C2B—N1B—H1B | 119.2 (13) | C4B—C42B—H45B | 110.00 |
C2B—N2B—H2B | 123.3 (13) | H44B—C42B—H45B | 110.00 |
S1B—N2B—H2B | 113.2 (13) | H43B—C42B—H45B | 109.00 |
C41B—N41B—H42B | 118.5 (14) | C61B—C51B—H51B | 120.00 |
C41B—N41B—H41B | 113.6 (15) | C41B—C51B—H51B | 120.00 |
H41B—N41B—H42B | 126 (2) | C11B—C61B—H61B | 120.00 |
O51C—N5C—C5C | 118.80 (16) | C51B—C61B—H61B | 120.00 |
O52C—N5C—C5C | 118.44 (15) | H63B—C62B—H65B | 109.00 |
O51C—N5C—O52C | 122.77 (15) | H64B—C62B—H65B | 109.00 |
O51D—N5D—O52D | 122.88 (14) | C6B—C62B—H64B | 109.00 |
O51D—N5D—C5D | 118.78 (15) | H63B—C62B—H64B | 109.00 |
O52D—N5D—C5D | 118.33 (13) | C6B—C62B—H65B | 110.00 |
N2A—C2A—N3A | 119.57 (14) | C6B—C62B—H63B | 110.00 |
N1A—C2A—N2A | 116.84 (13) | C2C—C1C—C11C | 121.10 (14) |
N1A—C2A—N3A | 123.59 (13) | C6C—C1C—C11C | 120.09 (14) |
N3A—C4A—C5A | 121.85 (14) | C2C—C1C—C6C | 118.81 (14) |
N3A—C4A—C42A | 116.05 (14) | O2C—C2C—C3C | 117.41 (14) |
C5A—C4A—C42A | 122.10 (14) | C1C—C2C—C3C | 120.42 (15) |
C4A—C5A—C6A | 118.89 (14) | O2C—C2C—C1C | 122.18 (14) |
N1A—C6A—C62A | 117.56 (13) | C2C—C3C—C4C | 120.33 (16) |
N1A—C6A—C5A | 118.17 (14) | C3C—C4C—C5C | 118.77 (16) |
C5A—C6A—C62A | 124.25 (14) | N5C—C5C—C6C | 119.24 (15) |
S1A—C11A—C61A | 120.29 (12) | C4C—C5C—C6C | 122.26 (15) |
S1A—C11A—C21A | 119.64 (12) | N5C—C5C—C4C | 118.49 (15) |
C21A—C11A—C61A | 120.07 (14) | C1C—C6C—C5C | 119.41 (15) |
C11A—C21A—C31A | 119.73 (15) | O12C—C11C—C1C | 116.00 (13) |
C21A—C31A—C41A | 120.69 (16) | O11C—C11C—O12C | 124.26 (14) |
N41A—C41A—C51A | 121.05 (15) | O11C—C11C—C1C | 119.73 (14) |
N41A—C41A—C31A | 120.09 (16) | C2C—C3C—H3C | 120.00 |
C31A—C41A—C51A | 118.82 (15) | C4C—C3C—H3C | 120.00 |
C41A—C51A—C61A | 120.76 (14) | C5C—C4C—H4C | 121.00 |
C11A—C61A—C51A | 119.92 (15) | C3C—C4C—H4C | 121.00 |
C6A—C5A—H5A | 121.00 | C1C—C6C—H6C | 120.00 |
C4A—C5A—H5A | 121.00 | C5C—C6C—H6C | 120.00 |
C31A—C21A—H21A | 120.00 | C2D—C1D—C11D | 121.32 (14) |
C11A—C21A—H21A | 120.00 | C6D—C1D—C11D | 119.92 (14) |
C41A—C31A—H31A | 120.00 | C2D—C1D—C6D | 118.77 (14) |
C21A—C31A—H31A | 120.00 | O2D—C2D—C1D | 122.23 (14) |
H43A—C42A—H45A | 110.00 | O2D—C2D—C3D | 117.38 (14) |
C4A—C42A—H44A | 109.00 | C1D—C2D—C3D | 120.39 (15) |
H44A—C42A—H45A | 109.00 | C2D—C3D—C4D | 120.31 (16) |
C4A—C42A—H43A | 109.00 | C3D—C4D—C5D | 118.98 (16) |
C4A—C42A—H45A | 109.00 | N5D—C5D—C6D | 119.27 (14) |
H43A—C42A—H44A | 109.00 | C4D—C5D—C6D | 121.93 (15) |
C61A—C51A—H51A | 120.00 | N5D—C5D—C4D | 118.78 (14) |
C41A—C51A—H51A | 120.00 | C1D—C6D—C5D | 119.61 (14) |
C51A—C61A—H61A | 120.00 | O11D—C11D—C1D | 120.77 (14) |
C11A—C61A—H61A | 120.00 | O12D—C11D—C1D | 115.61 (13) |
C6A—C62A—H63A | 109.00 | O11D—C11D—O12D | 123.62 (14) |
C6A—C62A—H64A | 109.00 | C2D—C3D—H3D | 120.00 |
H63A—C62A—H64A | 109.00 | C4D—C3D—H3D | 120.00 |
H64A—C62A—H65A | 109.00 | C3D—C4D—H4D | 120.00 |
C6A—C62A—H65A | 110.00 | C5D—C4D—H4D | 121.00 |
H63A—C62A—H65A | 109.00 | C1D—C6D—H6D | 120.00 |
N2B—C2B—N3B | 119.97 (14) | C5D—C6D—H6D | 120.00 |
O11A—S1A—N2A—C2A | −51.52 (14) | C11A—C21A—C31A—C41A | −1.7 (2) |
O12A—S1A—N2A—C2A | −179.01 (12) | C21A—C31A—C41A—C51A | 1.4 (2) |
C11A—S1A—N2A—C2A | 66.00 (14) | C21A—C31A—C41A—N41A | −176.06 (16) |
O11A—S1A—C11A—C21A | −160.97 (12) | N41A—C41A—C51A—C61A | 177.13 (16) |
O11A—S1A—C11A—C61A | 18.27 (15) | C31A—C41A—C51A—C61A | −0.3 (2) |
O12A—S1A—C11A—C21A | −27.88 (15) | C41A—C51A—C61A—C11A | −0.5 (2) |
O12A—S1A—C11A—C61A | 151.36 (13) | C42B—C4B—C5B—C6B | 178.39 (15) |
N2A—S1A—C11A—C21A | 81.64 (14) | N3B—C4B—C5B—C6B | −1.7 (2) |
N2A—S1A—C11A—C61A | −99.12 (14) | C4B—C5B—C6B—C62B | −179.08 (15) |
N2B—S1B—C11B—C21B | −78.04 (14) | C4B—C5B—C6B—N1B | 0.0 (2) |
N2B—S1B—C11B—C61B | 102.11 (14) | C21B—C11B—C61B—C51B | −0.7 (2) |
O11B—S1B—N2B—C2B | 59.70 (14) | S1B—C11B—C21B—C31B | −178.54 (12) |
O12B—S1B—N2B—C2B | −173.83 (12) | C61B—C11B—C21B—C31B | 1.3 (2) |
C11B—S1B—N2B—C2B | −58.59 (14) | S1B—C11B—C61B—C51B | 179.14 (12) |
O11B—S1B—C11B—C21B | 164.44 (12) | C11B—C21B—C31B—C41B | −0.2 (2) |
O11B—S1B—C11B—C61B | −15.41 (15) | C21B—C31B—C41B—C51B | −1.4 (2) |
O12B—S1B—C11B—C21B | 31.14 (15) | C21B—C31B—C41B—N41B | 176.95 (16) |
O12B—S1B—C11B—C61B | −148.71 (13) | C31B—C41B—C51B—C61B | 2.0 (2) |
C2A—N1A—C6A—C5A | 0.00 (19) | N41B—C41B—C51B—C61B | −176.33 (16) |
C2A—N1A—C6A—C62A | −178.53 (13) | C41B—C51B—C61B—C11B | −1.0 (2) |
C6A—N1A—C2A—N3A | 0.2 (2) | C6C—C1C—C2C—O2C | 178.79 (14) |
C6A—N1A—C2A—N2A | 179.44 (13) | C6C—C1C—C2C—C3C | −1.2 (2) |
S1A—N2A—C2A—N3A | −12.4 (2) | C2C—C1C—C11C—O11C | −177.96 (14) |
S1A—N2A—C2A—N1A | 168.33 (11) | C2C—C1C—C11C—O12C | 1.8 (2) |
C2A—N3A—C4A—C5A | −0.9 (2) | C6C—C1C—C11C—O11C | 1.9 (2) |
C4A—N3A—C2A—N1A | 0.3 (2) | C6C—C1C—C11C—O12C | −178.37 (14) |
C4A—N3A—C2A—N2A | −178.99 (13) | C11C—C1C—C2C—O2C | −1.4 (2) |
C2A—N3A—C4A—C42A | 178.67 (14) | C11C—C1C—C2C—C3C | 178.65 (14) |
C6B—N1B—C2B—N3B | 0.2 (2) | C2C—C1C—C6C—C5C | 1.0 (2) |
C2B—N1B—C6B—C5B | 0.7 (2) | C11C—C1C—C6C—C5C | −178.79 (13) |
C6B—N1B—C2B—N2B | −178.90 (13) | O2C—C2C—C3C—C4C | −179.05 (14) |
C2B—N1B—C6B—C62B | 179.89 (13) | C1C—C2C—C3C—C4C | 0.9 (2) |
S1B—N2B—C2B—N1B | 176.82 (10) | C2C—C3C—C4C—C5C | −0.5 (2) |
S1B—N2B—C2B—N3B | −2.3 (2) | C3C—C4C—C5C—C6C | 0.4 (2) |
C2B—N3B—C4B—C5B | 2.5 (2) | C3C—C4C—C5C—N5C | 179.12 (14) |
C2B—N3B—C4B—C42B | −177.57 (14) | N5C—C5C—C6C—C1C | −179.38 (13) |
C4B—N3B—C2B—N2B | 177.27 (13) | C4C—C5C—C6C—C1C | −0.7 (2) |
C4B—N3B—C2B—N1B | −1.8 (2) | C6D—C1D—C2D—O2D | 179.26 (15) |
O51C—N5C—C5C—C6C | 178.18 (15) | C6D—C1D—C2D—C3D | −0.2 (2) |
O51C—N5C—C5C—C4C | −0.6 (2) | C11D—C1D—C2D—O2D | −0.5 (2) |
O52C—N5C—C5C—C4C | 179.97 (16) | C11D—C1D—C2D—C3D | −180.00 (15) |
O52C—N5C—C5C—C6C | −1.3 (2) | C2D—C1D—C6D—C5D | −0.8 (2) |
O51D—N5D—C5D—C6D | 176.04 (15) | C11D—C1D—C6D—C5D | 179.02 (14) |
O52D—N5D—C5D—C6D | −2.8 (2) | C2D—C1D—C11D—O11D | −179.30 (15) |
O51D—N5D—C5D—C4D | −2.9 (2) | C2D—C1D—C11D—O12D | 1.1 (2) |
O52D—N5D—C5D—C4D | 178.27 (14) | C6D—C1D—C11D—O11D | 0.9 (2) |
N3A—C4A—C5A—C6A | 1.0 (2) | C6D—C1D—C11D—O12D | −178.73 (14) |
C42A—C4A—C5A—C6A | −178.48 (15) | O2D—C2D—C3D—C4D | −178.60 (15) |
C4A—C5A—C6A—C62A | 177.87 (14) | C1D—C2D—C3D—C4D | 0.9 (2) |
C4A—C5A—C6A—N1A | −0.6 (2) | C2D—C3D—C4D—C5D | −0.6 (2) |
C21A—C11A—C61A—C51A | 0.3 (2) | C3D—C4D—C5D—N5D | 178.47 (14) |
S1A—C11A—C61A—C51A | −178.96 (12) | C3D—C4D—C5D—C6D | −0.4 (2) |
S1A—C11A—C21A—C31A | −179.96 (13) | N5D—C5D—C6D—C1D | −177.77 (13) |
C61A—C11A—C21A—C31A | 0.8 (2) | C4D—C5D—C6D—C1D | 1.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O12D | 0.939 (18) | 1.647 (18) | 2.5847 (17) | 176 (2) |
N1B—H1B···O12C | 0.91 (2) | 1.71 (2) | 2.6162 (18) | 176.4 (18) |
N2A—H2A···O11D | 0.85 (2) | 1.94 (2) | 2.7810 (18) | 177 (2) |
N2B—H2B···O11C | 0.889 (19) | 1.836 (19) | 2.7221 (18) | 174.3 (18) |
N41A—H41A···O11Di | 0.82 (3) | 2.57 (2) | 3.217 (2) | 138 (2) |
N41B—H41B···O2Cii | 0.89 (2) | 2.49 (2) | 3.269 (2) | 147 (2) |
N41B—H42B···O12Biii | 0.83 (2) | 2.45 (2) | 3.106 (2) | 136.6 (18) |
O2C—H2C···O12C | 0.89 (3) | 1.70 (3) | 2.5223 (17) | 152 (2) |
O2D—H2D···O12D | 0.90 (2) | 1.70 (2) | 2.5215 (17) | 151 (2) |
C5A—H5A···O52Div | 0.95 | 2.56 | 3.4175 (19) | 150 |
C5B—H5B···O51Cv | 0.95 | 2.44 | 3.348 (2) | 160 |
C5B—H5B···O52Cv | 0.95 | 2.58 | 3.420 (2) | 147 |
C42A—H43A···O52Div | 0.98 | 2.49 | 3.428 (2) | 159 |
C42B—H45B···O52Cv | 0.98 | 2.42 | 3.350 (2) | 158 |
C61A—H61A···O11A | 0.95 | 2.59 | 2.9422 (19) | 102 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y−1, z; (v) x, y+1, z. |
C12H15N4O2S+·C6H2N3O7− | F(000) = 1048 |
Mr = 507.45 | Dx = 1.584 Mg m−3 |
Monoclinic, P21/c | Melting point = 469–471 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3131 (2) Å | Cell parameters from 7676 reflections |
b = 19.2779 (5) Å | θ = 3.2–28.8° |
c = 13.4483 (4) Å | µ = 0.22 mm−1 |
β = 99.158 (3)° | T = 200 K |
V = 2127.74 (10) Å3 | Block, yellow |
Z = 4 | 0.35 × 0.35 × 0.26 mm |
Oxford Gemini-S CCD area-detector diffractometer | 4171 independent reflections |
Radiation source: Enhance (Mo) X-ray source | 3318 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 16.077 pixels mm-1 | θmax = 26.0°, θmin = 3.3° |
ω scans | h = −8→10 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −23→23 |
Tmin = 0.970, Tmax = 0.981 | l = −15→16 |
14211 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0541P)2 + 0.1041P] where P = (Fo2 + 2Fc2)/3 |
4171 reflections | (Δ/σ)max = 0.005 |
334 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
C12H15N4O2S+·C6H2N3O7− | V = 2127.74 (10) Å3 |
Mr = 507.45 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.3131 (2) Å | µ = 0.22 mm−1 |
b = 19.2779 (5) Å | T = 200 K |
c = 13.4483 (4) Å | 0.35 × 0.35 × 0.26 mm |
β = 99.158 (3)° |
Oxford Gemini-S CCD area-detector diffractometer | 4171 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 3318 reflections with I > 2σ(I) |
Tmin = 0.970, Tmax = 0.981 | Rint = 0.024 |
14211 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.27 e Å−3 |
4171 reflections | Δρmin = −0.42 e Å−3 |
334 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1A | 1.01736 (5) | 0.72633 (2) | 0.40874 (3) | 0.0286 (1) | |
O11A | 1.01403 (16) | 0.74900 (6) | 0.30725 (10) | 0.0411 (4) | |
O12A | 0.91002 (15) | 0.75680 (6) | 0.46966 (11) | 0.0381 (4) | |
N1A | 0.81196 (16) | 0.54828 (6) | 0.42730 (11) | 0.0240 (4) | |
N2A | 0.96357 (18) | 0.64262 (7) | 0.39275 (12) | 0.0289 (5) | |
N3A | 0.95185 (16) | 0.61463 (7) | 0.56049 (10) | 0.0254 (4) | |
N41A | 1.6891 (2) | 0.73736 (9) | 0.62678 (16) | 0.0419 (6) | |
C2A | 0.90857 (19) | 0.60189 (8) | 0.46347 (13) | 0.0232 (5) | |
C4A | 0.89632 (19) | 0.57061 (8) | 0.62539 (13) | 0.0247 (5) | |
C5A | 0.79877 (19) | 0.51355 (8) | 0.59168 (13) | 0.0267 (5) | |
C6A | 0.75510 (18) | 0.50281 (8) | 0.49024 (13) | 0.0244 (5) | |
C11A | 1.2145 (2) | 0.72872 (8) | 0.47392 (13) | 0.0250 (5) | |
C21A | 1.3454 (2) | 0.72025 (8) | 0.42106 (13) | 0.0300 (6) | |
C31A | 1.5022 (2) | 0.72321 (9) | 0.47158 (14) | 0.0317 (6) | |
C41A | 1.5335 (2) | 0.73431 (8) | 0.57572 (13) | 0.0275 (5) | |
C42A | 0.9460 (2) | 0.58500 (9) | 0.73449 (13) | 0.0337 (6) | |
C51A | 1.4001 (2) | 0.74275 (8) | 0.62754 (14) | 0.0299 (6) | |
C61A | 1.2436 (2) | 0.73988 (8) | 0.57729 (13) | 0.0280 (5) | |
C62A | 0.6501 (2) | 0.44540 (9) | 0.44236 (15) | 0.0326 (6) | |
O1 | 0.81506 (14) | 0.55856 (6) | 0.23824 (9) | 0.0327 (4) | |
O21 | 0.51094 (17) | 0.58897 (8) | 0.28921 (10) | 0.0483 (5) | |
O22 | 0.35141 (16) | 0.52229 (7) | 0.18893 (11) | 0.0455 (5) | |
O41 | 0.33961 (17) | 0.59866 (9) | −0.16549 (11) | 0.0573 (6) | |
O42 | 0.56354 (17) | 0.63473 (7) | −0.20899 (10) | 0.0476 (5) | |
O61 | 1.06573 (16) | 0.58522 (8) | 0.01325 (11) | 0.0492 (5) | |
O62 | 1.06389 (16) | 0.62078 (8) | 0.16560 (11) | 0.0482 (5) | |
N2 | 0.46886 (17) | 0.56092 (7) | 0.20714 (11) | 0.0301 (5) | |
N4 | 0.48456 (19) | 0.61225 (8) | −0.14630 (12) | 0.0343 (5) | |
N6 | 0.99501 (17) | 0.59915 (8) | 0.08397 (12) | 0.0333 (5) | |
C1 | 0.7383 (2) | 0.57497 (8) | 0.15227 (12) | 0.0248 (5) | |
C2 | 0.56423 (19) | 0.57448 (8) | 0.12657 (12) | 0.0236 (5) | |
C3 | 0.4795 (2) | 0.58495 (8) | 0.03122 (13) | 0.0251 (5) | |
C4 | 0.5685 (2) | 0.60005 (8) | −0.04467 (13) | 0.0256 (5) | |
C5 | 0.7370 (2) | 0.60378 (8) | −0.02677 (13) | 0.0253 (5) | |
C6 | 0.81761 (19) | 0.59217 (8) | 0.06853 (13) | 0.0259 (5) | |
H42A | 1.706 (3) | 0.7434 (12) | 0.693 (2) | 0.061 (8)* | |
H1A | 0.784 (3) | 0.5461 (10) | 0.3591 (17) | 0.048 (6)* | |
H2A | 0.943 (2) | 0.6323 (10) | 0.3307 (16) | 0.037 (6)* | |
H5A | 0.76320 | 0.48260 | 0.63860 | 0.0320* | |
H21A | 1.32560 | 0.71250 | 0.35040 | 0.0360* | |
H31A | 1.59070 | 0.71770 | 0.43540 | 0.0380* | |
H41A | 1.771 (3) | 0.7388 (10) | 0.5900 (16) | 0.039 (6)* | |
H48A | 1.06370 | 0.57810 | 0.75290 | 0.0510* | 0.500 |
H43A | 0.88850 | 0.55330 | 0.77380 | 0.0510* | 0.500 |
H44A | 0.91840 | 0.63300 | 0.74880 | 0.0510* | 0.500 |
H45A | 0.85000 | 0.59820 | 0.76410 | 0.0510* | 0.500 |
H46A | 1.02530 | 0.62300 | 0.74320 | 0.0510* | 0.500 |
H47A | 0.99530 | 0.54330 | 0.76820 | 0.0510* | 0.500 |
H51A | 1.41910 | 0.75050 | 0.69820 | 0.0360* | |
H61A | 1.15470 | 0.74550 | 0.61310 | 0.0340* | |
H62A | 0.61050 | 0.41780 | 0.49470 | 0.0490* | |
H63A | 0.71360 | 0.41570 | 0.40390 | 0.0490* | |
H64A | 0.55710 | 0.46490 | 0.39700 | 0.0490* | |
H3 | 0.36400 | 0.58190 | 0.01800 | 0.0300* | |
H5 | 0.79580 | 0.61430 | −0.08000 | 0.0300* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0292 (2) | 0.0220 (2) | 0.0337 (3) | −0.0017 (2) | 0.0023 (2) | 0.0062 (2) |
O11A | 0.0486 (8) | 0.0353 (7) | 0.0360 (8) | −0.0070 (6) | −0.0037 (6) | 0.0162 (6) |
O12A | 0.0287 (7) | 0.0291 (7) | 0.0572 (9) | 0.0035 (5) | 0.0089 (6) | 0.0007 (6) |
N1A | 0.0241 (7) | 0.0244 (7) | 0.0228 (8) | −0.0015 (5) | 0.0016 (6) | 0.0012 (6) |
N2A | 0.0349 (8) | 0.0273 (8) | 0.0241 (9) | −0.0086 (6) | 0.0034 (7) | 0.0022 (6) |
N3A | 0.0256 (7) | 0.0250 (7) | 0.0253 (8) | −0.0006 (6) | 0.0036 (6) | −0.0002 (6) |
N41A | 0.0290 (9) | 0.0555 (11) | 0.0403 (11) | −0.0033 (7) | 0.0029 (8) | 0.0042 (8) |
C2A | 0.0207 (8) | 0.0210 (8) | 0.0280 (9) | 0.0009 (6) | 0.0045 (7) | 0.0006 (6) |
C4A | 0.0212 (8) | 0.0267 (8) | 0.0265 (9) | 0.0051 (6) | 0.0050 (7) | 0.0011 (7) |
C5A | 0.0256 (9) | 0.0267 (9) | 0.0292 (10) | 0.0008 (6) | 0.0089 (7) | 0.0049 (7) |
C6A | 0.0194 (8) | 0.0221 (8) | 0.0323 (10) | 0.0012 (6) | 0.0061 (7) | 0.0031 (7) |
C11A | 0.0264 (9) | 0.0203 (8) | 0.0286 (10) | −0.0028 (6) | 0.0054 (7) | 0.0032 (7) |
C21A | 0.0348 (10) | 0.0327 (9) | 0.0236 (10) | −0.0052 (7) | 0.0084 (7) | 0.0015 (7) |
C31A | 0.0284 (9) | 0.0350 (10) | 0.0347 (11) | −0.0029 (7) | 0.0138 (8) | 0.0017 (8) |
C41A | 0.0274 (9) | 0.0221 (8) | 0.0330 (10) | −0.0024 (6) | 0.0045 (7) | 0.0032 (7) |
C42A | 0.0379 (10) | 0.0370 (10) | 0.0266 (10) | −0.0003 (8) | 0.0064 (8) | −0.0009 (8) |
C51A | 0.0354 (10) | 0.0295 (9) | 0.0250 (10) | 0.0003 (7) | 0.0051 (8) | −0.0021 (7) |
C61A | 0.0297 (9) | 0.0255 (9) | 0.0309 (10) | 0.0010 (7) | 0.0114 (8) | −0.0023 (7) |
C62A | 0.0301 (9) | 0.0283 (9) | 0.0390 (11) | −0.0059 (7) | 0.0041 (8) | −0.0008 (8) |
O1 | 0.0325 (7) | 0.0420 (7) | 0.0225 (7) | −0.0006 (5) | 0.0009 (5) | 0.0029 (5) |
O21 | 0.0460 (8) | 0.0731 (10) | 0.0279 (8) | 0.0014 (7) | 0.0127 (6) | −0.0108 (7) |
O22 | 0.0446 (8) | 0.0470 (8) | 0.0493 (9) | −0.0146 (6) | 0.0213 (7) | 0.0014 (6) |
O41 | 0.0370 (9) | 0.0912 (12) | 0.0393 (9) | −0.0111 (8) | −0.0076 (7) | 0.0123 (8) |
O42 | 0.0496 (8) | 0.0635 (9) | 0.0298 (8) | 0.0009 (7) | 0.0071 (7) | 0.0190 (7) |
O61 | 0.0303 (7) | 0.0740 (10) | 0.0462 (9) | 0.0036 (6) | 0.0153 (7) | 0.0032 (7) |
O62 | 0.0344 (8) | 0.0657 (9) | 0.0420 (9) | −0.0154 (6) | −0.0012 (6) | −0.0027 (7) |
N2 | 0.0314 (8) | 0.0318 (8) | 0.0288 (9) | 0.0044 (6) | 0.0097 (7) | 0.0029 (6) |
N4 | 0.0355 (9) | 0.0371 (8) | 0.0288 (9) | 0.0012 (7) | 0.0008 (7) | 0.0043 (7) |
N6 | 0.0261 (8) | 0.0386 (8) | 0.0353 (9) | −0.0043 (6) | 0.0050 (7) | 0.0052 (7) |
C1 | 0.0303 (9) | 0.0217 (8) | 0.0224 (9) | −0.0014 (6) | 0.0042 (7) | −0.0030 (6) |
C2 | 0.0262 (9) | 0.0225 (8) | 0.0232 (9) | −0.0015 (6) | 0.0075 (7) | −0.0004 (6) |
C3 | 0.0227 (8) | 0.0225 (8) | 0.0298 (10) | −0.0015 (6) | 0.0030 (7) | −0.0005 (7) |
C4 | 0.0317 (10) | 0.0227 (8) | 0.0220 (9) | −0.0001 (7) | 0.0027 (7) | 0.0003 (7) |
C5 | 0.0301 (9) | 0.0234 (8) | 0.0240 (9) | −0.0030 (6) | 0.0090 (7) | 0.0010 (7) |
C6 | 0.0239 (9) | 0.0248 (8) | 0.0291 (10) | −0.0034 (6) | 0.0046 (7) | −0.0011 (7) |
S1A—O11A | 1.4292 (14) | C11A—C61A | 1.389 (2) |
S1A—O12A | 1.4301 (14) | C11A—C21A | 1.401 (2) |
S1A—N2A | 1.6792 (14) | C21A—C31A | 1.372 (2) |
S1A—C11A | 1.7318 (17) | C31A—C41A | 1.400 (3) |
O1—C1 | 1.269 (2) | C41A—C51A | 1.410 (2) |
O21—N2 | 1.229 (2) | C51A—C61A | 1.368 (2) |
O22—N2 | 1.221 (2) | C5A—H5A | 0.9500 |
O41—N4 | 1.220 (2) | C21A—H21A | 0.9500 |
O42—N4 | 1.227 (2) | C31A—H31A | 0.9500 |
O61—N6 | 1.225 (2) | C42A—H44A | 0.9800 |
O62—N6 | 1.228 (2) | C42A—H48A | 0.9800 |
N1A—C2A | 1.351 (2) | C42A—H43A | 0.9800 |
N1A—C6A | 1.355 (2) | C42A—H47A | 0.9800 |
N2A—C2A | 1.367 (2) | C42A—H45A | 0.9800 |
N3A—C4A | 1.350 (2) | C42A—H46A | 0.9800 |
N3A—C2A | 1.320 (2) | C51A—H51A | 0.9500 |
N41A—C41A | 1.366 (2) | C61A—H61A | 0.9500 |
N1A—H1A | 0.91 (2) | C62A—H62A | 0.9800 |
N2A—H2A | 0.85 (2) | C62A—H63A | 0.9800 |
N41A—H42A | 0.89 (3) | C62A—H64A | 0.9800 |
N41A—H41A | 0.90 (2) | C1—C2 | 1.433 (2) |
N2—C2 | 1.464 (2) | C1—C6 | 1.432 (2) |
N4—C4 | 1.451 (2) | C2—C3 | 1.376 (2) |
N6—C6 | 1.462 (2) | C3—C4 | 1.384 (2) |
C4A—C5A | 1.399 (2) | C4—C5 | 1.385 (2) |
C4A—C42A | 1.486 (2) | C5—C6 | 1.367 (2) |
C5A—C6A | 1.370 (2) | C3—H3 | 0.9500 |
C6A—C62A | 1.491 (2) | C5—H5 | 0.9500 |
O11A—S1A—O12A | 120.16 (8) | C4A—C5A—H5A | 120.00 |
O11A—S1A—N2A | 101.96 (8) | C11A—C21A—H21A | 120.00 |
O11A—S1A—C11A | 110.38 (8) | C31A—C21A—H21A | 120.00 |
O12A—S1A—N2A | 106.88 (7) | C41A—C31A—H31A | 120.00 |
O12A—S1A—C11A | 109.00 (8) | C21A—C31A—H31A | 120.00 |
N2A—S1A—C11A | 107.56 (8) | H43A—C42A—H44A | 109.00 |
C2A—N1A—C6A | 121.10 (15) | H45A—C42A—H46A | 109.00 |
S1A—N2A—C2A | 125.08 (13) | H45A—C42A—H47A | 109.00 |
C2A—N3A—C4A | 117.03 (14) | H46A—C42A—H47A | 110.00 |
C6A—N1A—H1A | 122.8 (14) | C4A—C42A—H47A | 109.00 |
C2A—N1A—H1A | 116.1 (14) | H48A—C42A—H43A | 109.00 |
C2A—N2A—H2A | 120.8 (13) | H48A—C42A—H44A | 110.00 |
S1A—N2A—H2A | 111.1 (13) | C4A—C42A—H43A | 109.00 |
H42A—N41A—H41A | 122 (2) | C4A—C42A—H44A | 109.00 |
C41A—N41A—H42A | 119.8 (16) | C4A—C42A—H45A | 109.00 |
C41A—N41A—H41A | 117.5 (14) | C4A—C42A—H46A | 109.00 |
O22—N2—C2 | 118.04 (14) | C4A—C42A—H48A | 109.00 |
O21—N2—O22 | 123.55 (15) | C41A—C51A—H51A | 120.00 |
O21—N2—C2 | 118.41 (14) | C61A—C51A—H51A | 120.00 |
O42—N4—C4 | 118.33 (15) | C51A—C61A—H61A | 120.00 |
O41—N4—O42 | 123.30 (16) | C11A—C61A—H61A | 120.00 |
O41—N4—C4 | 118.36 (15) | C6A—C62A—H63A | 110.00 |
O61—N6—O62 | 123.76 (15) | C6A—C62A—H64A | 109.00 |
O62—N6—C6 | 118.33 (15) | H62A—C62A—H64A | 109.00 |
O61—N6—C6 | 117.87 (15) | H63A—C62A—H64A | 109.00 |
N2A—C2A—N3A | 120.80 (15) | H62A—C62A—H63A | 109.00 |
N1A—C2A—N2A | 115.75 (15) | C6A—C62A—H62A | 109.00 |
N1A—C2A—N3A | 123.44 (15) | O1—C1—C2 | 124.07 (15) |
N3A—C4A—C42A | 116.81 (14) | O1—C1—C6 | 123.16 (15) |
C5A—C4A—C42A | 121.51 (15) | C2—C1—C6 | 112.68 (14) |
N3A—C4A—C5A | 121.67 (15) | N2—C2—C1 | 117.87 (14) |
C4A—C5A—C6A | 119.31 (15) | N2—C2—C3 | 117.30 (14) |
N1A—C6A—C62A | 116.68 (15) | C1—C2—C3 | 124.83 (15) |
N1A—C6A—C5A | 117.43 (14) | C2—C3—C4 | 117.63 (15) |
C5A—C6A—C62A | 125.89 (15) | N4—C4—C3 | 119.69 (15) |
S1A—C11A—C21A | 119.28 (13) | N4—C4—C5 | 118.47 (15) |
S1A—C11A—C61A | 120.71 (13) | C3—C4—C5 | 121.84 (16) |
C21A—C11A—C61A | 120.01 (16) | C4—C5—C6 | 119.07 (16) |
C11A—C21A—C31A | 119.83 (16) | N6—C6—C1 | 119.34 (15) |
C21A—C31A—C41A | 120.84 (16) | N6—C6—C5 | 116.80 (15) |
C31A—C41A—C51A | 118.47 (16) | C1—C6—C5 | 123.86 (15) |
N41A—C41A—C31A | 121.33 (16) | C2—C3—H3 | 121.00 |
N41A—C41A—C51A | 120.20 (17) | C4—C3—H3 | 121.00 |
C41A—C51A—C61A | 120.80 (17) | C4—C5—H5 | 120.00 |
C11A—C61A—C51A | 120.06 (16) | C6—C5—H5 | 120.00 |
C6A—C5A—H5A | 120.00 | ||
O11A—S1A—N2A—C2A | −162.41 (14) | N3A—C4A—C5A—C6A | −1.5 (2) |
O12A—S1A—N2A—C2A | −35.47 (17) | C42A—C4A—C5A—C6A | 179.47 (15) |
C11A—S1A—N2A—C2A | 81.46 (16) | C4A—C5A—C6A—C62A | −178.97 (15) |
O11A—S1A—C11A—C21A | −28.19 (15) | C4A—C5A—C6A—N1A | 1.0 (2) |
O11A—S1A—C11A—C61A | 150.90 (13) | S1A—C11A—C21A—C31A | 178.90 (13) |
O12A—S1A—C11A—C21A | −162.20 (12) | C61A—C11A—C21A—C31A | −0.2 (2) |
O12A—S1A—C11A—C61A | 16.88 (15) | S1A—C11A—C61A—C51A | −178.95 (12) |
N2A—S1A—C11A—C21A | 82.26 (14) | C21A—C11A—C61A—C51A | 0.1 (2) |
N2A—S1A—C11A—C61A | −98.65 (14) | C11A—C21A—C31A—C41A | 0.3 (2) |
C6A—N1A—C2A—N2A | 177.49 (14) | C21A—C31A—C41A—C51A | −0.3 (2) |
C6A—N1A—C2A—N3A | −1.2 (2) | C21A—C31A—C41A—N41A | −180.00 (16) |
C2A—N1A—C6A—C5A | 0.3 (2) | C31A—C41A—C51A—C61A | 0.3 (2) |
C2A—N1A—C6A—C62A | −179.73 (14) | N41A—C41A—C51A—C61A | 179.94 (16) |
S1A—N2A—C2A—N1A | 154.00 (12) | C41A—C51A—C61A—C11A | −0.2 (2) |
S1A—N2A—C2A—N3A | −27.3 (2) | O1—C1—C2—N2 | 6.3 (2) |
C4A—N3A—C2A—N1A | 0.7 (2) | O1—C1—C2—C3 | −172.77 (15) |
C4A—N3A—C2A—N2A | −177.96 (15) | C6—C1—C2—N2 | −177.07 (13) |
C2A—N3A—C4A—C5A | 0.7 (2) | C6—C1—C2—C3 | 3.8 (2) |
C2A—N3A—C4A—C42A | 179.73 (14) | O1—C1—C6—N6 | −7.2 (2) |
O21—N2—C2—C3 | −138.41 (16) | O1—C1—C6—C5 | 173.80 (15) |
O22—N2—C2—C1 | −137.67 (15) | C2—C1—C6—N6 | 176.16 (14) |
O22—N2—C2—C3 | 41.5 (2) | C2—C1—C6—C5 | −2.8 (2) |
O21—N2—C2—C1 | 42.4 (2) | N2—C2—C3—C4 | 177.92 (14) |
O41—N4—C4—C3 | −10.9 (2) | C1—C2—C3—C4 | −3.0 (2) |
O42—N4—C4—C3 | 170.19 (15) | C2—C3—C4—N4 | −179.35 (14) |
O42—N4—C4—C5 | −10.0 (2) | C2—C3—C4—C5 | 0.8 (2) |
O41—N4—C4—C5 | 168.93 (16) | N4—C4—C5—C6 | −179.78 (14) |
O61—N6—C6—C5 | −30.7 (2) | C3—C4—C5—C6 | 0.0 (2) |
O62—N6—C6—C1 | −32.2 (2) | C4—C5—C6—N6 | −177.92 (14) |
O62—N6—C6—C5 | 146.91 (16) | C4—C5—C6—C1 | 1.1 (2) |
O61—N6—C6—C1 | 150.26 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O1 | 0.91 (2) | 1.70 (2) | 2.5545 (19) | 154 (2) |
N1A—H1A···O21 | 0.91 (2) | 2.46 (2) | 2.974 (2) | 116.2 (18) |
N2A—H2A···O1 | 0.85 (2) | 2.07 (2) | 2.7661 (19) | 139.2 (17) |
N2A—H2A···O62 | 0.85 (2) | 2.59 (2) | 3.319 (2) | 145.0 (15) |
N41A—H41A···O12Ai | 0.90 (2) | 2.16 (2) | 3.035 (2) | 163 (2) |
Symmetry code: (i) x+1, y, z. |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C12H15N4O2S+·C7H4NO5− | C12H15N4O2S+·C6H2N3O7− |
Mr | 461.46 | 507.45 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/c |
Temperature (K) | 200 | 200 |
a, b, c (Å) | 13.1611 (2), 14.0977 (2), 22.1219 (3) | 8.3131 (2), 19.2779 (5), 13.4483 (4) |
β (°) | 90.094 (2) | 99.158 (3) |
V (Å3) | 4104.52 (10) | 2127.74 (10) |
Z | 8 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.21 | 0.22 |
Crystal size (mm) | 0.35 × 0.35 × 0.15 | 0.35 × 0.35 × 0.26 |
Data collection | ||
Diffractometer | Oxford Gemini-S Ultra CCD area-detector diffractometer | Oxford Gemini-S CCD area-detector diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.960, 0.980 | 0.970, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30179, 8057, 5991 | 14211, 4171, 3318 |
Rint | 0.025 | 0.024 |
(sin θ/λ)max (Å−1) | 0.617 | 0.617 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.090, 0.95 | 0.034, 0.091, 1.04 |
No. of reflections | 8057 | 4171 |
No. of parameters | 621 | 334 |
No. of restraints | 1 | 0 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.30 | 0.27, −0.42 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O12D | 0.939 (18) | 1.647 (18) | 2.5847 (17) | 176 (2) |
N1B—H1B···O12C | 0.91 (2) | 1.71 (2) | 2.6162 (18) | 176.4 (18) |
N2A—H2A···O11D | 0.85 (2) | 1.94 (2) | 2.7810 (18) | 177 (2) |
N2B—H2B···O11C | 0.889 (19) | 1.836 (19) | 2.7221 (18) | 174.3 (18) |
N41A—H41A···O11Di | 0.82 (3) | 2.57 (2) | 3.217 (2) | 138 (2) |
N41B—H41B···O2Cii | 0.89 (2) | 2.49 (2) | 3.269 (2) | 147 (2) |
N41B—H42B···O12Biii | 0.83 (2) | 2.45 (2) | 3.106 (2) | 136.6 (18) |
O2C—H2C···O12C | 0.89 (3) | 1.70 (3) | 2.5223 (17) | 152 (2) |
O2D—H2D···O12D | 0.90 (2) | 1.70 (2) | 2.5215 (17) | 151 (2) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x+3/2, y+1/2, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O1 | 0.91 (2) | 1.70 (2) | 2.5545 (19) | 154 (2) |
N1A—H1A···O21 | 0.91 (2) | 2.46 (2) | 2.974 (2) | 116.2 (18) |
N2A—H2A···O1 | 0.85 (2) | 2.07 (2) | 2.7661 (19) | 139.2 (17) |
N2A—H2A···O62 | 0.85 (2) | 2.59 (2) | 3.319 (2) | 145.0 (15) |
N41A—H41A···O12Ai | 0.90 (2) | 2.16 (2) | 3.035 (2) | 163 (2) |
Symmetry code: (i) x+1, y, z. |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- Purchase subscription
- Reduced-price subscriptions
- If you have already subscribed, you may need to register
The drug sulfamethazine [or sulfadimidine; systematic name: 4-amino-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide] (O'Neil, 2001) has been used as a model for cocrystal formation (Caira, 2007; Ghosh et al., 2011), commonly forming 1:1 adducts with carboxylic acids, predominantly the benzoic acid analogues. The structures of a significant number of these have been reported, e.g. with benzoic acid (Arman et al., 2010), salicylic acid (Patel et al., 1988), anthranilic and 4-aminobenzoic acids (Caira, 1991), 4-aminosalicylic and acetylsalicylic acids (Caira, 1992), 2-nitrobenzoic acid (Smith & Wermuth, 2013a), 4-nitrobenzoic acid (Smith & Wermuth, 2012), 2,4-dinitrobenzoic and indole-2-carboxylic acids (Lynch et al., 2000), 4-chlorobenzoic acid (Lucaciu et al., 2008), and 4-hydroxybenzoic, 2,4-dihydroxybenzoic, 3,4-dichlorobenzoic, 1-hydroxy-2-naphthoic and 3-hydroxy-2-naphthoic acids (Ghosh et al., 2011). Only two aliphatic examples are known, viz. with fumaric and sorbic acids. The structures of the cocrystals with the amides benzamide, 4-hydroxybenzamide and picolinamide (Ghosh et al., 2011) are also known. The structures of the adducts with trimethoprim, viz. a 1:1 methanol monosolvate (Bettinetti & Sardone, 1997) and a 2:1 monohydrate (Sardone et al., 1997), represent a small number of solvated examples.
In the previously mentioned cocrystals of sulfamethazine, heterodimers are usually formed through a cyclic hydrogen-bonding motif [graph set R22(8); Etter et al., 1990], involving amide N—H···Ocarboxylate and carboxylic acid O—H···Npyrimidine pairs. Other structures not involving carboxylic acids are the 1:1 complex with saccharin (Lu et al., 2008), where a protonated sulfamethazine cation is present, and the 2:1 complex with theophylline (Lu et al., 2011), in which two tautomeric forms of sulfamethazine are found: the amidine and the imidine forms, similar to those found in the benzamide cocrystal (Ghosh et al., 2011). The structures of the parent compound sulfamethazine (Tiwari et al., 1984) and its methanol monosolvate (Rambaud et al., 1985) are also known.
However, no examples of proton-transfer salts of sulfamethzine with strong `conventional' organic acids were present in the crystallographic literature before that of the structure of the anhydrous picrate salt with 3,5-dinitrosalicylic acid (DNSA) (Smith & Wermuth, 2013b). In this salt, a hydrogen-bonded heterodimer analogous to those in the non-proton-transfer cocrystals is present, the subtle variation being that, with proton transfer, one N+—H···Ocarboxylate and one N—H···Ocarboxylate interaction are involved in the R22(8) motif. The phenolate group is only involved in the intramolecular cyclic carboxylic acid O—H···O hydrogen bond, similar to that found in the majority of the proton-transfer salts of DNSA (Smith et al., 2007). We therefore carried out the reaction of sulfamethazine with other strong organic acids under similar conditions to those used in the DNSA preparation (1:1 stoichiomety in 50% ethanol–water). Suitable crystalline products were obtained with 5-nitrosalicylic acid (5-NSA) and picric acid, the title salts 2-(4-aminobenzenesulfonamido)-4,6-dimethylpyrimidinium 2-hydroxy-5-nitrobenzoate, (I) (Fig. 1), and 2-(4-aminobenzenesulfonamido)-4,6-dimethylpyrimidinium 2,4,6-trinitrophenolate, (II) (Fig. 2), and the structures are reported herein. Although not as effective as picric acid for producing crystalline proton-transfer salts with amines, 5-NSA (pKa ~2.2) has proved relatively useful in this respect, particularly with the aromatic amines (Smith et al., 1996, 2005, 2006; Kumar et al., 2003).
In the 5-NSA salt of sulfamethazine, (I), the asymmetric unit (Fig. 1) contains two independent cation–anion pairs (cations labelled A and B, and anions labelled C and D, respectively), which interact through N—H···Ocarboxylate hydrogen-bonding pairs (Table 1), giving cyclic R22(8) heterodimers (A–D and B–C). These differ from the heterodimer adduct only in the presence in (I) of the transferred H atom on the pyrimidine N atom of the sulfamethazine cation. Asymmetry is found in the N+—H···O [2.5847 (17) Å (A) and 2.6162 (18) Å (B)] and N—H···O distances [2.7810 (18) Å (A) and 2.7221 (18) Å (B)] within the cyclic association. This asymmetry is comparable with that found in the cocrystal examples [O—H···N and N—H···O ranges for eight examples (Lynch et al., 2000) are 2.526 (4)–2.724 (4) and 2.719 (4)–2.840 (4) Å, respectively]. The corresponding values in the DNSA proton-transfer salt (Smith & Wermuth, 2013b) are 2.617 (4) and 2.729 (4) Å.
In (I), the cyclic motifs result in near-coplanarity of the pyrimidinium and 5-NSA ring systems, with inter-ring dihedral angles of 3.74 (7) and 7.84 (7)° for dimers A–D and B–C, respectively. [Please check amended text] The heterodimers form separate and different non-associated substructures through aniline N—H···O hydrogen bonds (Table 1), the first system being one-dimensional (A–D), involving carboxylate O-atom acceptors (O11D) and extending parallel to [010] (Fig. 3a). The second system (B–C) is two-dimensional, involving both carboxylate and salicylate O-atom acceptors (O12B and O2C, respectively), and extends parallel to the (011) plane (Fig. 3b). The composite structure of (I) is two-dimensional (Fig. 3c), lying in the (101) plane. Unlike the structure of the sulfamethazine salt with 3,5-dinitrosalicylic acid, no intermolecular aniline N—H···Osulfone hydrogen-bonding interactions are present. However, π–π interactions are present between the pyrimidine rings of both cations and both anions [A···.C and B···D; ring-centroid separations (Cg···Cg) = 3.4580 (8) and 3.6815 (9) Å, respectively].
For picrate salt (II) (Fig. 2), the pyrimidine ring of the sulfamethazine molecule (A) is protonated at N1A and this group, together with the adjacent amide N2A—H group, gives a slighly asymmetric chelating hydrogen-bonding association with the picrate anion through a cyclic R21(6) motif. Conjoint lateral R12(6) cyclic associations are also formed between the N1A—H donor group and the O-atom acceptors of adjacent ortho-related picrate nitro groups (Table 2). A single intermolecular amine N41A—H···Osulfone hydrogen-bonding interaction between the cation–anion units gives one-dimensional chains which extend along the a cell direction (Fig. 4). Also present in the structure are π–π interactions between the pyrimidine rings of centosymmetrically related sulfamethazine cations [Cg··· Cgii = 3.4752 (9) Å; symmetry code: (ii) -x+2, -y+1, -z+1] (Fig. 5). As found in the two structures reported here and in many of the sulfamethazine adduct structures, the 4-amino ring-substituent group is often only weakly or partially involved in hydrogen-bonding associations in the crystal structures. The nitro groups of the picrate anion are variously rotated out of the plane of the benzene ring [torsion angles C1—C2—N2—O22, C3—C4—N4—O42 and C5—C6—N6—O62 of -137.67 (15), 170.19 (15) and 146.91 (16)°, respectively].
In the sulfamethazine cations, the conformation differs significantly between carboxylate (I) and picrate (II). For (I), the dihedral angles between the pyrimidinium and benzene rings of the sulfamethazine cations are 70.60 (7) (A) and 84.78 (7)° (B), compared with 78.77 (8) and 82.33 (9)° for those in the two independent heterodimers in the 4-nitrobenzoic acid adduct (Smith & Wermuth, 2012). The value for the equivalent pyrimidinium–benzene dihedral angle in the cation of (II) [58.18 (7)°] is similar to that in the picrate salt with DNSA [59.70 (17)°], but is significantly smaller than commonly found in the other adduct structures and in (I), and probably in the case of (II) is attributable to the markedly different hydrogen-bonding pattern present in that structure. In (I), the two interacting pyrimidine–5-NSA dimers are essentially planar, with inter-ring dihedral angles of 3.74 (7) and 7.84 (7)°, compared with 12.2 (2)° in the structure of the DNSA salt (Smith & Wermuth, 2013b).
The two structures presented here now give a small total of four crystallographically characterized examples of proton-transfer salts of sulfamethazine with strong organic acids.