(S)-N⁵-Ethyl-N²-(2-nitro­phenyl­sulfon­yl)glutamine

The title compound, C₁₃H₁₇N₃O₇S, is a potential AHAS (acetohydroxy­acid synthase) inhibitor. In the crystal structure, the nitro group is twisted away from the plane of the aromatic ring and the glutamine residue adopts a folded conformation. The crystal packing is stabilized by inter­molecular N—H...O and O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.026
• wR factor = 0.070
• Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       5.68 su
PLAT352_ALERT_3_C Short   N-H Bond (0.87A)   N3     -   H3     ...       0.73 Ang.

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           26.34
           From the CIF: _reflns_number_total               2469
           Count of symmetry unique reflns         1756
           Completeness (_total/calc)            140.60%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       713
           Fraction of Friedel pairs measured     0.406
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1999); 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.

N⁵-Ethyl-N²-(2-nitrophenylsulfonyl)glutamine

Crystal data

C13H17N3O7S	F(000) = 376
Mr = 359.36	Dx = 1.498 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3215 reflections
a = 6.7756 (10) Å	θ = 3.0–26.3°
b = 7.4223 (11) Å	µ = 0.25 mm^−1
c = 15.848 (2) Å	T = 294 K
β = 91.901 (2)°	Block, colourless
V = 796.6 (2) Å^3	0.22 × 0.16 × 0.14 mm
Z = 2

Data collection

Bruker SMART CCD diffractometer	2469 independent reflections
Radiation source: fine-focus sealed tube	2350 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
ω scans	θmax = 26.3°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→8
Tmin = 0.928, Tmax = 0.966	k = −9→6
4510 measured reflections	l = −17→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap and geom
R[F^2 > 2σ(F^2)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.070	w = 1/[σ^2(Fo^2) + (0.0391P)^2 + 0.0864P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2469 reflections	Δρmax = 0.15 e Å^−3
227 parameters	Δρmin = −0.21 e Å^−3
1 restraint	Absolute structure: Flack (1983), 722 Friedel Pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.08 (6)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.79947 (6)	0.27419 (7)	0.31172 (3)	0.03397 (13)
O1	1.3321 (3)	0.4111 (3)	0.44370 (10)	0.0583 (5)
O2	1.2203 (2)	0.4254 (2)	0.31489 (10)	0.0509 (4)
O3	0.8120 (2)	0.4371 (3)	0.35925 (9)	0.0491 (4)
O4	0.61658 (19)	0.1785 (3)	0.30393 (9)	0.0488 (4)
O5	1.15624 (19)	0.3029 (3)	0.11000 (9)	0.0495 (5)
O6	0.9897 (2)	0.1235 (3)	0.02040 (10)	0.0507 (5)
H6	1.077 (4)	0.136 (5)	−0.0104 (18)	0.061*
O7	0.7497 (2)	0.6650 (3)	0.09009 (9)	0.0497 (4)
N1	1.2416 (2)	0.3476 (3)	0.38251 (11)	0.0376 (4)
N2	0.8665 (2)	0.3191 (2)	0.21722 (9)	0.0311 (4)
H2	0.967 (3)	0.378 (4)	0.2182 (13)	0.037*
N3	0.4772 (3)	0.5789 (3)	0.15432 (13)	0.0432 (5)
H3	0.403 (4)	0.508 (4)	0.1531 (17)	0.052*
C1	1.1611 (3)	0.1659 (3)	0.39100 (11)	0.0330 (4)
C2	1.2822 (3)	0.0420 (3)	0.43173 (13)	0.0432 (5)
H2A	1.4052	0.0768	0.4538	0.052*
C3	1.2193 (4)	−0.1346 (4)	0.43948 (14)	0.0511 (6)
H3A	1.3017	−0.2197	0.4655	0.061*
C4	1.0355 (4)	−0.1841 (4)	0.40883 (14)	0.0527 (6)
H4	0.9930	−0.3024	0.4145	0.063*
C5	0.9125 (3)	−0.0572 (3)	0.36928 (12)	0.0425 (5)
H5	0.7873	−0.0918	0.3496	0.051*
C6	0.9728 (3)	0.1192 (3)	0.35868 (11)	0.0323 (4)
C7	0.8422 (2)	0.1861 (3)	0.14914 (11)	0.0295 (4)
H7	0.8519	0.0653	0.1739	0.035*
C8	1.0154 (3)	0.2123 (3)	0.09055 (12)	0.0335 (4)
C9	0.6403 (2)	0.2038 (3)	0.10281 (11)	0.0312 (4)
H9A	0.6226	0.1016	0.0651	0.037*
H9B	0.5381	0.1975	0.1441	0.037*
C10	0.6112 (3)	0.3766 (3)	0.05151 (11)	0.0351 (5)
H10A	0.7121	0.3811	0.0095	0.042*
H10B	0.4844	0.3697	0.0215	0.042*
C11	0.6186 (3)	0.5503 (3)	0.10062 (12)	0.0332 (4)
C12	0.4620 (3)	0.7358 (4)	0.20878 (16)	0.0527 (6)
H12A	0.5668	0.8198	0.1964	0.063*
H12B	0.4802	0.6984	0.2672	0.063*
C13	0.2668 (5)	0.8293 (5)	0.19777 (17)	0.0695 (8)
H13A	0.1622	0.7447	0.2065	0.104*
H13B	0.2541	0.8777	0.1417	0.104*
H13C	0.2592	0.9253	0.2381	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0267 (2)	0.0467 (3)	0.0286 (2)	0.0018 (2)	0.00264 (15)	−0.0021 (2)
O1	0.0614 (10)	0.0542 (12)	0.0580 (10)	−0.0106 (9)	−0.0191 (8)	−0.0113 (9)
O2	0.0501 (9)	0.0495 (11)	0.0524 (9)	−0.0132 (8)	−0.0085 (7)	0.0163 (9)
O3	0.0527 (9)	0.0557 (11)	0.0389 (7)	0.0135 (8)	0.0018 (6)	−0.0125 (8)
O4	0.0271 (7)	0.0772 (13)	0.0424 (7)	−0.0061 (8)	0.0047 (5)	0.0028 (8)
O5	0.0291 (6)	0.0726 (14)	0.0470 (7)	−0.0117 (8)	0.0041 (5)	−0.0038 (9)
O6	0.0426 (9)	0.0641 (12)	0.0463 (9)	0.0001 (8)	0.0149 (7)	−0.0171 (9)
O7	0.0474 (8)	0.0549 (11)	0.0478 (8)	−0.0171 (8)	0.0162 (6)	0.0029 (8)
N1	0.0302 (8)	0.0403 (10)	0.0419 (9)	−0.0009 (7)	−0.0035 (7)	−0.0013 (8)
N2	0.0275 (7)	0.0375 (11)	0.0282 (7)	−0.0046 (7)	−0.0009 (6)	−0.0008 (7)
N3	0.0327 (9)	0.0376 (11)	0.0603 (11)	−0.0053 (8)	0.0170 (8)	−0.0074 (10)
C1	0.0347 (9)	0.0357 (12)	0.0288 (9)	0.0000 (9)	0.0020 (7)	−0.0017 (8)
C2	0.0446 (12)	0.0483 (15)	0.0363 (10)	0.0052 (10)	−0.0048 (9)	0.0032 (10)
C3	0.0633 (14)	0.0439 (14)	0.0458 (12)	0.0105 (12)	−0.0015 (10)	0.0086 (11)
C4	0.0785 (16)	0.0352 (14)	0.0449 (11)	−0.0042 (11)	0.0105 (11)	0.0050 (10)
C5	0.0495 (12)	0.0438 (13)	0.0344 (10)	−0.0125 (10)	0.0045 (9)	−0.0008 (10)
C6	0.0336 (9)	0.0391 (12)	0.0243 (8)	−0.0020 (8)	0.0030 (7)	−0.0006 (9)
C7	0.0264 (8)	0.0312 (10)	0.0309 (8)	0.0013 (8)	0.0009 (7)	−0.0017 (8)
C8	0.0265 (9)	0.0402 (12)	0.0338 (9)	0.0084 (8)	0.0012 (7)	0.0020 (9)
C9	0.0241 (8)	0.0377 (11)	0.0317 (9)	−0.0046 (8)	−0.0009 (7)	−0.0046 (8)
C10	0.0282 (8)	0.0492 (13)	0.0279 (9)	0.0040 (9)	0.0002 (7)	0.0019 (9)
C11	0.0273 (9)	0.0412 (12)	0.0311 (9)	0.0020 (8)	0.0005 (7)	0.0091 (9)
C12	0.0536 (13)	0.0453 (16)	0.0602 (13)	−0.0071 (11)	0.0165 (10)	−0.0069 (12)
C13	0.0887 (19)	0.067 (2)	0.0544 (14)	0.0308 (16)	0.0200 (13)	−0.0004 (14)

Geometric parameters (Å, º)

S1—O3	1.4254 (19)	C3—H3A	0.9300
S1—O4	1.4301 (16)	C4—C5	1.392 (3)
S1—N2	1.6141 (16)	C4—H4	0.9300
S1—C6	1.789 (2)	C5—C6	1.383 (3)
O1—N1	1.224 (2)	C5—H5	0.9300
O2—N1	1.222 (2)	C7—C8	1.533 (3)
O5—C8	1.200 (3)	C7—C9	1.537 (2)
O6—C8	1.299 (3)	C7—H7	0.9800
O6—H6	0.79 (3)	C9—C10	1.528 (3)
O7—C11	1.245 (3)	C9—H9A	0.9700
N1—C1	1.462 (3)	C9—H9B	0.9700
N2—C7	1.468 (2)	C10—C11	1.506 (3)
N2—H2	0.81 (2)	C10—H10A	0.9700
N3—C11	1.320 (3)	C10—H10B	0.9700
N3—C12	1.455 (3)	C12—C13	1.499 (4)
N3—H3	0.73 (3)	C12—H12A	0.9700
C1—C2	1.378 (3)	C12—H12B	0.9700
C1—C6	1.403 (3)	C13—H13A	0.9600
C2—C3	1.386 (4)	C13—H13B	0.9600
C2—H2A	0.9300	C13—H13C	0.9600
C3—C4	1.372 (3)
O3—S1—O4	120.21 (10)	N2—C7—C9	111.73 (15)
O3—S1—N2	107.55 (10)	C8—C7—C9	112.77 (15)
O4—S1—N2	106.99 (9)	N2—C7—H7	108.4
O3—S1—C6	107.39 (9)	C8—C7—H7	108.4
O4—S1—C6	105.74 (10)	C9—C7—H7	108.4
N2—S1—C6	108.53 (8)	O5—C8—O6	125.95 (18)
C8—O6—H6	113 (2)	O5—C8—C7	122.27 (17)
O2—N1—O1	123.7 (2)	O6—C8—C7	111.77 (17)
O2—N1—C1	118.87 (17)	C10—C9—C7	115.02 (16)
O1—N1—C1	117.44 (18)	C10—C9—H9A	108.5
C7—N2—S1	121.01 (14)	C7—C9—H9A	108.5
C7—N2—H2	116.9 (16)	C10—C9—H9B	108.5
S1—N2—H2	110.9 (15)	C7—C9—H9B	108.5
C11—N3—C12	125.3 (2)	H9A—C9—H9B	107.5
C11—N3—H3	113 (2)	C11—C10—C9	116.25 (14)
C12—N3—H3	122 (2)	C11—C10—H10A	108.2
C2—C1—C6	121.7 (2)	C9—C10—H10A	108.2
C2—C1—N1	116.11 (18)	C11—C10—H10B	108.2
C6—C1—N1	122.16 (18)	C9—C10—H10B	108.2
C1—C2—C3	119.5 (2)	H10A—C10—H10B	107.4
C1—C2—H2A	120.2	O7—C11—N3	120.9 (2)
C3—C2—H2A	120.2	O7—C11—C10	121.83 (18)
C4—C3—C2	120.0 (2)	N3—C11—C10	117.30 (19)
C4—C3—H3A	120.0	N3—C12—C13	112.4 (2)
C2—C3—H3A	120.0	N3—C12—H12A	109.1
C3—C4—C5	120.1 (2)	C13—C12—H12A	109.1
C3—C4—H4	119.9	N3—C12—H12B	109.1
C5—C4—H4	119.9	C13—C12—H12B	109.1
C6—C5—C4	121.3 (2)	H12A—C12—H12B	107.9
C6—C5—H5	119.3	C12—C13—H13A	109.5
C4—C5—H5	119.3	C12—C13—H13B	109.5
C5—C6—C1	117.30 (19)	H13A—C13—H13B	109.5
C5—C6—S1	117.83 (15)	C12—C13—H13C	109.5
C1—C6—S1	124.71 (17)	H13A—C13—H13C	109.5
N2—C7—C8	106.90 (15)	H13B—C13—H13C	109.5
O3—S1—N2—C7	−170.87 (13)	O4—S1—C6—C5	6.94 (18)
O4—S1—N2—C7	−40.45 (17)	N2—S1—C6—C5	−107.56 (16)
C6—S1—N2—C7	73.24 (15)	O3—S1—C6—C1	−38.88 (18)
O2—N1—C1—C2	135.9 (2)	O4—S1—C6—C1	−168.39 (16)
O1—N1—C1—C2	−42.1 (3)	N2—S1—C6—C1	77.12 (17)
O2—N1—C1—C6	−43.2 (3)	S1—N2—C7—C8	−146.42 (13)
O1—N1—C1—C6	138.7 (2)	S1—N2—C7—C9	89.76 (18)
C6—C1—C2—C3	1.6 (3)	N2—C7—C8—O5	12.4 (3)
N1—C1—C2—C3	−177.6 (2)	C9—C7—C8—O5	135.5 (2)
C1—C2—C3—C4	−1.8 (4)	N2—C7—C8—O6	−168.63 (17)
C2—C3—C4—C5	0.5 (4)	C9—C7—C8—O6	−45.4 (2)
C3—C4—C5—C6	1.1 (3)	N2—C7—C9—C10	67.6 (2)
C4—C5—C6—C1	−1.3 (3)	C8—C7—C9—C10	−52.8 (2)
C4—C5—C6—S1	−177.02 (17)	C7—C9—C10—C11	−62.6 (2)
C2—C1—C6—C5	0.0 (3)	C12—N3—C11—O7	−3.2 (3)
N1—C1—C6—C5	179.14 (19)	C12—N3—C11—C10	178.3 (2)
C2—C1—C6—S1	175.37 (16)	C9—C10—C11—O7	115.8 (2)
N1—C1—C6—S1	−5.5 (3)	C9—C10—C11—N3	−65.7 (2)
O3—S1—C6—C5	136.45 (16)	C11—N3—C12—C13	125.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O5	0.81 (2)	2.25 (2)	2.641 (2)	110.7 (19)
N2—H2···O2	0.81 (2)	2.29 (2)	2.918 (2)	135 (2)
N3—H3···O5^i	0.73 (3)	2.35 (3)	3.053 (3)	164 (3)
O6—H6···O7^ii	0.79 (3)	1.77 (3)	2.546 (2)	173 (3)

Symmetry codes: (i) x−1, y, z; (ii) −x+2, y−1/2, −z.