Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030114/ci6653sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030114/ci6653Isup2.hkl |
CCDC reference: 287528
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.029
- wR factor = 0.068
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.44 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 .. 6.57 su PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.06
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.36 From the CIF: _reflns_number_total 3293 Count of symmetry unique reflns 1863 Completeness (_total/calc) 176.76% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1430 Fraction of Friedel pairs measured 0.768 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Compound (I) was prepared according to the procedure of Srikanth et al. (2002). Colourless single crystals suitable for X-ray diffraction analysis were obtained by recrystallization from ethanol and water (8:2 v/v).
The amine and hydroxy H atoms were located in a difference map and refined isotropically (see Table 2 for distances). The C-bound H atoms were placed in calculated positions, with C—H = 0.93–0.98 Å, and included in the final cycles of refinement using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C14H19N3O7S | F(000) = 392 |
Mr = 373.38 | Dx = 1.463 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2760 reflections |
a = 6.9215 (13) Å | θ = 2.9–26.2° |
b = 7.7539 (16) Å | µ = 0.23 mm−1 |
c = 15.797 (3) Å | T = 294 K |
β = 91.858 (3)° | Prism, colourless |
V = 847.3 (3) Å3 | 0.26 × 0.20 × 0.18 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 3293 independent reflections |
Radiation source: fine-focus sealed tube | 2977 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→5 |
Tmin = 0.935, Tmax = 0.959 | k = −9→9 |
4767 measured reflections | l = −16→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.069 | w = 1/[σ2(Fo2) + (0.029P)2 + 0.1123P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
3293 reflections | Δρmax = 0.14 e Å−3 |
239 parameters | Δρmin = −0.17 e Å−3 |
19 restraints | Absolute structure: Flack (1983), 1439 Friedel Pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (6) |
C14H19N3O7S | V = 847.3 (3) Å3 |
Mr = 373.38 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.9215 (13) Å | µ = 0.23 mm−1 |
b = 7.7539 (16) Å | T = 294 K |
c = 15.797 (3) Å | 0.26 × 0.20 × 0.18 mm |
β = 91.858 (3)° |
Bruker SMART CCD area-detector diffractometer | 3293 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2977 reflections with I > 2σ(I) |
Tmin = 0.935, Tmax = 0.959 | Rint = 0.018 |
4767 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.069 | Δρmax = 0.14 e Å−3 |
S = 1.06 | Δρmin = −0.17 e Å−3 |
3293 reflections | Absolute structure: Flack (1983), 1439 Friedel Pairs |
239 parameters | Absolute structure parameter: 0.00 (6) |
19 restraints |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
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 | ||
S1 | 0.18001 (6) | 0.51289 (6) | 0.68311 (3) | 0.03880 (12) | |
O1 | −0.3398 (3) | 0.6233 (3) | 0.55017 (11) | 0.0717 (5) | |
O2 | −0.2398 (2) | 0.6410 (2) | 0.68034 (10) | 0.0639 (5) | |
O3 | 0.1560 (2) | 0.6676 (2) | 0.63517 (9) | 0.0549 (4) | |
O4 | 0.36377 (19) | 0.4296 (2) | 0.68935 (9) | 0.0573 (4) | |
O5 | −0.1683 (2) | 0.5317 (2) | 0.88503 (9) | 0.0569 (4) | |
O6 | −0.0053 (2) | 0.3581 (2) | 0.97427 (10) | 0.0565 (4) | |
H6 | −0.096 (4) | 0.366 (4) | 1.0065 (18) | 0.077 (9)* | |
O7 | 0.2637 (2) | 0.8944 (2) | 0.91572 (10) | 0.0593 (4) | |
N1 | −0.2546 (2) | 0.5661 (2) | 0.61264 (12) | 0.0460 (4) | |
N2 | 0.1168 (2) | 0.5534 (2) | 0.77864 (9) | 0.0353 (4) | |
H2A | 0.015 (3) | 0.605 (3) | 0.7804 (12) | 0.032 (5)* | |
N3 | 0.4870 (2) | 0.7868 (2) | 0.83201 (11) | 0.0439 (4) | |
H3A | 0.552 (3) | 0.699 (3) | 0.8216 (12) | 0.036 (6)* | |
C1 | −0.1706 (3) | 0.3927 (3) | 0.60670 (11) | 0.0390 (4) | |
C2 | −0.2864 (4) | 0.2677 (3) | 0.56901 (14) | 0.0525 (6) | |
H2 | −0.4089 | 0.2961 | 0.5474 | 0.063* | |
C3 | −0.2199 (4) | 0.1008 (3) | 0.56359 (15) | 0.0624 (7) | |
H3 | −0.2987 | 0.0152 | 0.5399 | 0.075* | |
C4 | −0.0358 (4) | 0.0613 (3) | 0.59349 (14) | 0.0644 (7) | |
H4 | 0.0098 | −0.0512 | 0.5893 | 0.077* | |
C5 | 0.0824 (3) | 0.1880 (3) | 0.62986 (13) | 0.0506 (6) | |
H5 | 0.2072 | 0.1599 | 0.6487 | 0.061* | |
C6 | 0.0162 (3) | 0.3560 (2) | 0.63831 (11) | 0.0364 (4) | |
C7 | 0.1436 (2) | 0.4253 (3) | 0.84651 (11) | 0.0338 (4) | |
H7 | 0.1355 | 0.3105 | 0.8207 | 0.041* | |
C8 | −0.0298 (3) | 0.4461 (3) | 0.90434 (12) | 0.0389 (4) | |
C9 | 0.3402 (3) | 0.4401 (3) | 0.89322 (12) | 0.0380 (4) | |
H9A | 0.3554 | 0.3423 | 0.9312 | 0.046* | |
H9B | 0.4406 | 0.4322 | 0.8520 | 0.046* | |
C10 | 0.3718 (3) | 0.6050 (3) | 0.94448 (12) | 0.0413 (5) | |
H10A | 0.2728 | 0.6109 | 0.9864 | 0.050* | |
H10B | 0.4954 | 0.5958 | 0.9749 | 0.050* | |
C11 | 0.3693 (3) | 0.7717 (3) | 0.89619 (12) | 0.0382 (4) | |
C12 | 0.4937 (3) | 0.9371 (3) | 0.77660 (13) | 0.0528 (6) | |
H12A | 0.3679 | 0.9922 | 0.7743 | 0.063* | |
H12B | 0.5221 | 0.8996 | 0.7198 | 0.063* | |
C13 | 0.6454 (4) | 1.0679 (3) | 0.80635 (16) | 0.0644 (7) | |
H13A | 0.6504 | 1.1601 | 0.7650 | 0.077* | |
H13B | 0.6061 | 1.1178 | 0.8594 | 0.077* | |
C14 | 0.8432 (4) | 0.9928 (4) | 0.81882 (18) | 0.0734 (7) | |
H14A | 0.8842 | 0.9444 | 0.7664 | 0.110* | |
H14B | 0.8407 | 0.9041 | 0.8612 | 0.110* | |
H14C | 0.9319 | 1.0817 | 0.8369 | 0.110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0325 (2) | 0.0509 (3) | 0.0333 (2) | −0.0019 (2) | 0.00619 (17) | 0.0019 (2) |
O1 | 0.0708 (11) | 0.0736 (12) | 0.0696 (11) | 0.0181 (10) | −0.0181 (9) | 0.0120 (10) |
O2 | 0.0600 (10) | 0.0616 (11) | 0.0692 (11) | 0.0183 (8) | −0.0100 (8) | −0.0251 (10) |
O3 | 0.0642 (10) | 0.0564 (10) | 0.0443 (8) | −0.0143 (8) | 0.0036 (7) | 0.0116 (7) |
O4 | 0.0339 (7) | 0.0891 (12) | 0.0495 (8) | 0.0076 (8) | 0.0101 (6) | −0.0030 (8) |
O5 | 0.0358 (7) | 0.0788 (12) | 0.0567 (8) | 0.0096 (8) | 0.0123 (6) | 0.0106 (9) |
O6 | 0.0477 (9) | 0.0739 (12) | 0.0487 (9) | −0.0050 (8) | 0.0153 (7) | 0.0179 (8) |
O7 | 0.0567 (9) | 0.0686 (11) | 0.0540 (9) | 0.0197 (8) | 0.0215 (7) | −0.0025 (8) |
N1 | 0.0363 (9) | 0.0493 (12) | 0.0520 (11) | 0.0046 (8) | −0.0026 (8) | 0.0009 (9) |
N2 | 0.0292 (8) | 0.0433 (10) | 0.0335 (8) | 0.0030 (7) | 0.0019 (6) | 0.0007 (7) |
N3 | 0.0359 (9) | 0.0445 (11) | 0.0523 (10) | 0.0040 (8) | 0.0160 (8) | 0.0008 (9) |
C1 | 0.0430 (11) | 0.0423 (11) | 0.0317 (9) | −0.0001 (9) | 0.0020 (8) | 0.0002 (8) |
C2 | 0.0563 (14) | 0.0604 (15) | 0.0405 (11) | −0.0094 (11) | −0.0025 (10) | −0.0070 (11) |
C3 | 0.0868 (19) | 0.0510 (14) | 0.0493 (13) | −0.0098 (13) | 0.0000 (13) | −0.0117 (11) |
C4 | 0.106 (2) | 0.0380 (13) | 0.0500 (13) | 0.0072 (12) | 0.0117 (13) | −0.0061 (10) |
C5 | 0.0653 (15) | 0.0486 (13) | 0.0380 (11) | 0.0155 (11) | 0.0041 (10) | −0.0011 (10) |
C6 | 0.0427 (11) | 0.0405 (11) | 0.0264 (9) | 0.0036 (9) | 0.0054 (7) | −0.0019 (8) |
C7 | 0.0328 (10) | 0.0338 (10) | 0.0350 (9) | −0.0027 (8) | 0.0046 (7) | −0.0004 (8) |
C8 | 0.0338 (10) | 0.0438 (11) | 0.0393 (10) | −0.0116 (9) | 0.0052 (8) | −0.0031 (9) |
C9 | 0.0303 (9) | 0.0457 (11) | 0.0384 (10) | 0.0060 (8) | 0.0050 (8) | 0.0038 (9) |
C10 | 0.0311 (10) | 0.0597 (13) | 0.0332 (10) | −0.0027 (9) | 0.0036 (8) | −0.0008 (9) |
C11 | 0.0273 (9) | 0.0512 (12) | 0.0362 (10) | −0.0017 (8) | 0.0002 (7) | −0.0104 (9) |
C12 | 0.0523 (13) | 0.0627 (14) | 0.0438 (11) | 0.0145 (12) | 0.0087 (9) | 0.0053 (11) |
C13 | 0.103 (2) | 0.0396 (13) | 0.0520 (13) | 0.0030 (13) | 0.0188 (13) | 0.0066 (10) |
C14 | 0.0671 (16) | 0.0681 (18) | 0.0850 (17) | −0.0279 (14) | 0.0025 (13) | 0.0056 (15) |
S1—O3 | 1.4255 (16) | C4—C5 | 1.391 (3) |
S1—O4 | 1.4269 (15) | C4—H4 | 0.93 |
S1—N2 | 1.6157 (16) | C5—C6 | 1.389 (3) |
S1—C6 | 1.793 (2) | C5—H5 | 0.93 |
O1—N1 | 1.216 (2) | C7—C9 | 1.531 (3) |
O2—N1 | 1.218 (2) | C7—C8 | 1.540 (2) |
O5—C8 | 1.198 (2) | C7—H7 | 0.98 |
O6—C8 | 1.305 (2) | C9—C10 | 1.526 (3) |
O6—H6 | 0.82 (3) | C9—H9A | 0.97 |
O7—C11 | 1.245 (2) | C9—H9B | 0.97 |
N1—C1 | 1.470 (3) | C10—C11 | 1.501 (3) |
N2—C7 | 1.469 (2) | C10—H10A | 0.97 |
N2—H2A | 0.81 (2) | C10—H10B | 0.97 |
N3—C11 | 1.326 (2) | C12—C13 | 1.523 (4) |
N3—C12 | 1.459 (3) | C12—H12A | 0.97 |
N3—H3A | 0.83 (2) | C12—H12B | 0.97 |
C1—C2 | 1.380 (3) | C13—C14 | 1.495 (4) |
C1—C6 | 1.400 (3) | C13—H13A | 0.97 |
C2—C3 | 1.377 (4) | C13—H13B | 0.97 |
C2—H2 | 0.93 | C14—H14A | 0.96 |
C3—C4 | 1.379 (4) | C14—H14B | 0.96 |
C3—H3 | 0.93 | C14—H14C | 0.96 |
O3—S1—O4 | 120.39 (10) | C9—C7—H7 | 107.9 |
O3—S1—N2 | 107.58 (9) | C8—C7—H7 | 107.9 |
O4—S1—N2 | 106.92 (8) | O5—C8—O6 | 125.90 (18) |
O3—S1—C6 | 107.45 (9) | O5—C8—C7 | 122.67 (17) |
O4—S1—C6 | 105.73 (10) | O6—C8—C7 | 111.43 (18) |
N2—S1—C6 | 108.29 (8) | C10—C9—C7 | 115.36 (16) |
C8—O6—H6 | 114 (2) | C10—C9—H9A | 108.4 |
O1—N1—O2 | 124.29 (18) | C7—C9—H9A | 108.4 |
O1—N1—C1 | 117.65 (18) | C10—C9—H9B | 108.4 |
O2—N1—C1 | 118.02 (17) | C7—C9—H9B | 108.4 |
C7—N2—S1 | 121.24 (13) | H9A—C9—H9B | 107.5 |
C7—N2—H2A | 113.5 (14) | C11—C10—C9 | 116.94 (14) |
S1—N2—H2A | 112.9 (13) | C11—C10—H10A | 108.1 |
C11—N3—C12 | 124.19 (18) | C9—C10—H10A | 108.1 |
C11—N3—H3A | 115.3 (14) | C11—C10—H10B | 108.1 |
C12—N3—H3A | 120.3 (14) | C9—C10—H10B | 108.1 |
C2—C1—C6 | 121.9 (2) | H10A—C10—H10B | 107.3 |
C2—C1—N1 | 116.37 (18) | O7—C11—N3 | 120.13 (19) |
C6—C1—N1 | 121.74 (17) | O7—C11—C10 | 121.98 (17) |
C3—C2—C1 | 119.7 (2) | N3—C11—C10 | 117.88 (17) |
C3—C2—H2 | 120.1 | N3—C12—C13 | 112.45 (18) |
C1—C2—H2 | 120.1 | N3—C12—H12A | 109.1 |
C2—C3—C4 | 119.7 (2) | C13—C12—H12A | 109.1 |
C2—C3—H3 | 120.2 | N3—C12—H12B | 109.1 |
C4—C3—H3 | 120.2 | C13—C12—H12B | 109.1 |
C3—C4—C5 | 120.6 (2) | H12A—C12—H12B | 107.8 |
C3—C4—H4 | 119.7 | C14—C13—C12 | 113.6 (2) |
C5—C4—H4 | 119.7 | C14—C13—H13A | 108.8 |
C6—C5—C4 | 120.7 (2) | C12—C13—H13A | 108.8 |
C6—C5—H5 | 119.6 | C14—C13—H13B | 108.8 |
C4—C5—H5 | 119.6 | C12—C13—H13B | 108.8 |
C5—C6—C1 | 117.39 (19) | H13A—C13—H13B | 107.7 |
C5—C6—S1 | 117.90 (16) | C13—C14—H14A | 109.5 |
C1—C6—S1 | 124.61 (15) | C13—C14—H14B | 109.5 |
N2—C7—C9 | 112.97 (15) | H14A—C14—H14B | 109.5 |
N2—C7—C8 | 106.26 (15) | C13—C14—H14C | 109.5 |
C9—C7—C8 | 113.82 (14) | H14A—C14—H14C | 109.5 |
N2—C7—H7 | 107.9 | H14B—C14—H14C | 109.5 |
O3—S1—N2—C7 | −173.61 (13) | N2—S1—C6—C5 | −105.60 (16) |
O4—S1—N2—C7 | −42.98 (16) | O3—S1—C6—C1 | −37.70 (17) |
C6—S1—N2—C7 | 70.54 (15) | O4—S1—C6—C1 | −167.46 (15) |
O1—N1—C1—C2 | −45.2 (3) | N2—S1—C6—C1 | 78.24 (17) |
O2—N1—C1—C2 | 132.6 (2) | S1—N2—C7—C9 | 89.94 (17) |
O1—N1—C1—C6 | 135.4 (2) | S1—N2—C7—C8 | −144.58 (13) |
O2—N1—C1—C6 | −46.8 (3) | N2—C7—C8—O5 | 11.2 (3) |
C6—C1—C2—C3 | 1.5 (3) | C9—C7—C8—O5 | 136.1 (2) |
N1—C1—C2—C3 | −177.9 (2) | N2—C7—C8—O6 | −169.67 (16) |
C1—C2—C3—C4 | −2.0 (4) | C9—C7—C8—O6 | −44.7 (2) |
C2—C3—C4—C5 | 0.7 (4) | N2—C7—C9—C10 | 66.3 (2) |
C3—C4—C5—C6 | 1.3 (3) | C8—C7—C9—C10 | −55.0 (2) |
C4—C5—C6—C1 | −1.8 (3) | C7—C9—C10—C11 | −62.7 (2) |
C4—C5—C6—S1 | −178.25 (16) | C12—N3—C11—O7 | −4.5 (3) |
C2—C1—C6—C5 | 0.5 (3) | C12—N3—C11—C10 | 176.71 (19) |
N1—C1—C6—C5 | 179.84 (18) | C9—C10—C11—O7 | 127.2 (2) |
C2—C1—C6—S1 | 176.64 (15) | C9—C10—C11—N3 | −54.1 (2) |
N1—C1—C6—S1 | −4.0 (3) | C11—N3—C12—C13 | 93.2 (2) |
O3—S1—C6—C5 | 138.46 (15) | N3—C12—C13—C14 | 54.2 (3) |
O4—S1—C6—C5 | 8.71 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O7i | 0.82 (3) | 1.73 (3) | 2.549 (2) | 172 (3) |
N2—H2A···O5 | 0.81 (2) | 2.192 (19) | 2.639 (2) | 115 (2) |
N2—H2A···O2 | 0.81 (2) | 2.347 (19) | 2.952 (2) | 132 (2) |
N3—H3A···O5ii | 0.83 (2) | 2.52 (2) | 3.190 (2) | 139 (2) |
Symmetry codes: (i) −x, y−1/2, −z+2; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C14H19N3O7S |
Mr | 373.38 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 294 |
a, b, c (Å) | 6.9215 (13), 7.7539 (16), 15.797 (3) |
β (°) | 91.858 (3) |
V (Å3) | 847.3 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.26 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.935, 0.959 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4767, 3293, 2977 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.069, 1.06 |
No. of reflections | 3293 |
No. of parameters | 239 |
No. of restraints | 19 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.14, −0.17 |
Absolute structure | Flack (1983), 1439 Friedel Pairs |
Absolute structure parameter | 0.00 (6) |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
S1—N2 | 1.6157 (16) | N1—C1 | 1.470 (3) |
S1—C6 | 1.793 (2) | N2—C7 | 1.469 (2) |
O5—C8 | 1.198 (2) | N3—C11 | 1.326 (2) |
O6—C8 | 1.305 (2) | N3—C12 | 1.459 (3) |
O7—C11 | 1.245 (2) | ||
O5—C8—O6 | 125.90 (18) | O7—C11—C10 | 121.98 (17) |
O6—C8—C7 | 111.43 (18) | N3—C12—C13 | 112.45 (18) |
O1—N1—C1—C2 | −45.2 (3) | C12—N3—C11—O7 | −4.5 (3) |
O2—N1—C1—C2 | 132.6 (2) | C9—C10—C11—O7 | 127.2 (2) |
O1—N1—C1—C6 | 135.4 (2) | C9—C10—C11—N3 | −54.1 (2) |
O2—N1—C1—C6 | −46.8 (3) | N3—C12—C13—C14 | 54.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H6···O7i | 0.82 (3) | 1.73 (3) | 2.549 (2) | 172 (3) |
N2—H2A···O5 | 0.81 (2) | 2.192 (19) | 2.639 (2) | 115 (2) |
N2—H2A···O2 | 0.81 (2) | 2.347 (19) | 2.952 (2) | 132 (2) |
N3—H3A···O5ii | 0.83 (2) | 2.52 (2) | 3.190 (2) | 139 (2) |
Symmetry codes: (i) −x, y−1/2, −z+2; (ii) x+1, y, z. |
Based on the reported 2.8 Å high-resolution crystal structure of yeast AHAS (acetohydroxyacid synthase) complex (Pang et al., 2003), we obtained 300 molecules with low binding energy toward AHAS from MDL/ACD three-dimensional database searching, using the program DOCK 4.0 (Wang et al., 2005). These potential structures provide information for further design of new targeted AHAS herbicidal molecules. According to the structural information and bioactivity data of 5-N-substituted-2-(substituted benzenesulfonyl)glutamine, a series of these derivatives have been designed and synthesized. The X-ray crystal structure determination of the title compound, (I), was undertaken to investigate the relationship between structure and herbicidal activity.
The bond lengths and angles in (I) show normal values (Table 1). The O3—S1—O4 angle [120.39 (10)°] deviates significantly from the ideal tetrahedral value. The O—N—C—C torsion angles indicate that the nitro group is twisted away from the plane of the benzene ring (Fig. 1). In the glutamine residue, the ψ1 (N2—C7—C8—O5), ψ2 (N2—C7—C8—O6), χ1 (N2—C7—C9—C10) and χ2 (C7—C9—C10—C11) torsion angles are 11.2 (3), −169.67 (16), 66.3 (2) and −62.7 (2)°, respectively; the two planar groups in the residue, C7/C8/O5/O6 and C10/C11/O7/N3, form a dihedral angle of 32.0 (1)°.
The molecular structure is stabilized by intramolecular N—H···O hydrogen bonds (Table 2). The crystal structure involves intermolecular O—H···O and N—H···O hydrogen bonds, which link the molecules into a layer parallel to the ab plane (Fig. 2).