N-(2-Nitro­phenyl­sulfonyl)glycine methyl ester

The structure of the title compound, C₉H₁₀N₂O₆S, has been determined as part of an ongoing investigation into the preparation of N-allyl-substituted amino acids suitable for alkene cross-metathesis reactions in the generation of combinatorial libraries. The conformational structure is determined by intra- and intermolecular N—H...O and C—H...O hydrogen-bonding interactions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.050
• wR factor = 0.206
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

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Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC7 Diffractometer Control Software for Windows (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control Software for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON.

N-(2-Nitrophenylsulfonyl)glycine methyl ester

Crystal data

C9H10N2O6S	F(000) = 568
Mr = 274.26	Dx = 1.579 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 19.805 (3) Å	θ = 12.6–15.8°
b = 7.988 (2) Å	µ = 0.30 mm^−1
c = 7.369 (2) Å	T = 295 K
β = 98.18 (2)°	Prism, colorless
V = 1153.9 (5) Å^3	0.50 × 0.30 × 0.30 mm
Z = 4

Data collection

Rigaku AFC-7R diffractometer	Rint = 0.035
Radiation source: Rigaku rotating-anode	θmax = 25.0°, θmin = 2.8°
Graphite monochromator	h = −11→23
ω–2θ scans	k = 0→9
2280 measured reflections	l = −8→8
2037 independent reflections	3 standard reflections every 150 reflections
1621 reflections with I > 2σ(I)	intensity decay: 0.3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.206	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.1367P)^2 + 0.8688P] where P = (Fo^2 + 2Fc^2)/3
2037 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.40 e Å^−3
0 restraints	Δρmin = −0.56 e Å^−3

Special details

Experimental. The scan width was (1.79 + 0.30tanθ)° with an ω scan speed of 16° per minute (up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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 > 2σ(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	0.26243 (4)	0.50077 (10)	0.93936 (12)	0.0373 (3)
O1	0.13296 (18)	0.6575 (4)	1.0531 (5)	0.0650 (11)
O2	0.05205 (17)	0.6008 (5)	0.8356 (6)	0.0808 (14)
O3	0.23320 (16)	0.6311 (4)	0.8198 (4)	0.0580 (10)
O4	0.31893 (14)	0.4074 (4)	0.8945 (4)	0.0561 (10)
O5	0.40773 (16)	0.7240 (4)	1.0891 (5)	0.0626 (11)
O6	0.46370 (13)	0.5366 (3)	1.2802 (4)	0.0492 (9)
N1	0.28386 (15)	0.5743 (4)	1.1414 (4)	0.0433 (10)
N2	0.10259 (16)	0.5631 (4)	0.9403 (5)	0.0474 (11)
C1	0.19546 (17)	0.3520 (4)	0.9502 (4)	0.0304 (9)
C2	0.12700 (18)	0.3902 (4)	0.9360 (5)	0.0356 (10)
C3	0.0775 (2)	0.2660 (6)	0.9238 (6)	0.0493 (12)
C4	0.0976 (2)	0.1003 (5)	0.9307 (6)	0.0526 (14)
C5	0.1653 (2)	0.0596 (5)	0.9479 (5)	0.0483 (14)
C6	0.2140 (2)	0.1844 (4)	0.9570 (5)	0.0404 (11)
C7	0.34658 (19)	0.5296 (5)	1.2533 (5)	0.0413 (11)
C8	0.40842 (19)	0.6104 (4)	1.1944 (5)	0.0397 (11)
C9	0.5291 (2)	0.6045 (6)	1.2505 (8)	0.0651 (18)
H1	0.26160	0.65790	1.17070	0.0690*
H3	0.03070	0.29430	0.91160	0.0630*
H4	0.06520	0.01330	0.92290	0.0640*
H5	0.17880	−0.05470	0.95480	0.0580*
H6	0.26100	0.15500	0.96780	0.0480*
H7A	0.34370	0.56250	1.37700	0.0520*
H7B	0.35150	0.41230	1.24820	0.0520*
H9A	0.52740	0.62870	1.12270	0.0780*
H9B	0.56350	0.52520	1.28660	0.0780*
H9C	0.53730	0.70430	1.31860	0.0780*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0389 (6)	0.0343 (6)	0.0395 (6)	−0.0076 (3)	0.0084 (4)	−0.0030 (3)
O1	0.075 (2)	0.0358 (16)	0.081 (2)	0.0085 (15)	0.0001 (17)	−0.0085 (15)
O2	0.050 (2)	0.075 (2)	0.109 (3)	0.0242 (17)	−0.0174 (19)	0.006 (2)
O3	0.067 (2)	0.0490 (16)	0.0551 (17)	−0.0197 (14)	−0.0009 (14)	0.0187 (14)
O4	0.0439 (15)	0.0622 (19)	0.0663 (19)	−0.0108 (13)	0.0216 (13)	−0.0237 (15)
O5	0.0591 (18)	0.0516 (18)	0.073 (2)	−0.0089 (14)	−0.0044 (15)	0.0255 (16)
O6	0.0413 (15)	0.0371 (14)	0.0674 (18)	0.0000 (11)	0.0016 (13)	0.0082 (13)
N1	0.0393 (17)	0.0395 (18)	0.0493 (18)	0.0017 (13)	−0.0003 (13)	−0.0136 (14)
N2	0.0436 (18)	0.0396 (18)	0.059 (2)	0.0051 (15)	0.0069 (15)	0.0021 (16)
C1	0.0333 (17)	0.0296 (16)	0.0282 (15)	−0.0031 (13)	0.0042 (12)	−0.0022 (12)
C2	0.0384 (18)	0.0327 (18)	0.0356 (17)	−0.0014 (14)	0.0052 (14)	−0.0007 (14)
C3	0.040 (2)	0.056 (2)	0.052 (2)	−0.0110 (18)	0.0072 (16)	−0.0018 (19)
C4	0.066 (3)	0.043 (2)	0.050 (2)	−0.025 (2)	0.0123 (19)	−0.0033 (18)
C5	0.073 (3)	0.0294 (19)	0.042 (2)	−0.0084 (18)	0.0062 (18)	−0.0022 (16)
C6	0.050 (2)	0.0320 (18)	0.0395 (18)	0.0020 (15)	0.0076 (15)	−0.0026 (15)
C7	0.042 (2)	0.0376 (18)	0.0436 (19)	−0.0057 (15)	0.0033 (16)	−0.0025 (15)
C8	0.046 (2)	0.0290 (17)	0.0433 (19)	−0.0016 (15)	0.0039 (15)	−0.0001 (15)
C9	0.040 (2)	0.055 (3)	0.099 (4)	−0.006 (2)	0.005 (2)	0.010 (3)

Geometric parameters (Å, º)

S1—O3	1.432 (3)	C2—C3	1.389 (6)
S1—O4	1.422 (3)	C3—C4	1.381 (6)
S1—N1	1.601 (3)	C4—C5	1.368 (6)
S1—C1	1.791 (3)	C5—C6	1.382 (5)
O1—N2	1.216 (5)	C7—C8	1.502 (5)
O2—N2	1.212 (5)	C3—H3	0.9458
O5—C8	1.193 (5)	C4—H4	0.9421
O6—C8	1.322 (5)	C5—H5	0.9507
O6—C9	1.449 (5)	C6—H6	0.9523
N1—C7	1.435 (5)	C7—H7A	0.9581
N2—C2	1.465 (5)	C7—H7B	0.9433
N1—H1	0.8450	C9—H9A	0.9573
C1—C6	1.387 (5)	C9—H9B	0.9405
C1—C2	1.379 (5)	C9—H9C	0.9437
S1···O1	3.075 (4)	O5···H7A^vi	2.5289
S1···O5	3.431 (3)	O6···H9C^x	2.7517
O1···S1	3.075 (4)	N1···O1	3.040 (5)
O1···O3	2.813 (5)	N1···O5	2.805 (4)
O1···N1	3.040 (5)	N1···O3^iii	2.941 (4)
O1···C5^i	3.387 (5)	N2···O3	2.903 (5)
O1···C5^ii	3.369 (5)	C3···O2^xi	3.253 (6)
O1···O3^iii	3.090 (5)	C4···O2^xi	3.314 (6)
O2···C4^iv	3.314 (6)	C5···O1^xii	3.387 (5)
O2···C3^iv	3.253 (6)	C5···O1^v	3.369 (5)
O3···N2	2.903 (5)	C5···O3^ii	3.254 (5)
O3···O1	2.813 (5)	C7···O5^iii	3.257 (5)
O3···C5^v	3.254 (5)	C8···O4	3.089 (5)
O3···N1^vi	2.941 (4)	C8···O5^iii	3.197 (5)
O3···O1^vi	3.090 (5)	C9···O4^vii	3.335 (5)
O4···C8	3.089 (5)	C7···H6^ii	2.8823
O4···C9^vii	3.335 (5)	H1···O1	2.5717
O5···S1	3.431 (3)	H1···O3^iii	2.1307
O5···N1	2.805 (4)	H3···O2	2.5600
O5···C7^vi	3.257 (5)	H3···O2^xi	2.7466
O5···C8^vi	3.197 (5)	H3···O2^viii	2.7797
O1···H5^i	2.6117	H4···O2^xi	2.8724
O1···H1	2.5717	H5···O1^xii	2.6117
O2···H4^iv	2.8724	H5···O3^ii	2.8183
O2···H3^iv	2.7466	H6···O4	2.4185
O2···H3	2.5600	H6···C7^v	2.8823
O2···H3^viii	2.7797	H6···H7A^v	2.5417
O3···H1^vi	2.1307	H7A···O5^iii	2.5289
O3···H5^v	2.8183	H7A···H6^ii	2.5417
O4···H7B	2.5947	H7B···O4	2.5947
O4···H6	2.4185	H7B···O4^ii	2.8805
O4···H9B^vii	2.8942	H9A···O5	2.4680
O4···H7B^v	2.8805	H9B···O5^x	2.6084
O5···H9B^ix	2.6084	H9B···O4^vii	2.8942
O5···H9A	2.4680	H9C···O5	2.8697
O5···H9C	2.8697	H9C···O6^ix	2.7517
O3—S1—O4	120.06 (18)	N1—C7—C8	113.7 (3)
O3—S1—N1	109.64 (17)	O6—C8—C7	108.9 (3)
O3—S1—C1	105.83 (17)	O5—C8—O6	125.6 (4)
O4—S1—N1	107.18 (17)	O5—C8—C7	125.5 (4)
O4—S1—C1	105.93 (17)	C2—C3—H3	120.58
N1—S1—C1	107.58 (15)	C4—C3—H3	120.40
C8—O6—C9	117.2 (3)	C3—C4—H4	120.96
S1—N1—C7	122.4 (3)	C5—C4—H4	118.72
O1—N2—O2	124.4 (4)	C4—C5—H5	119.85
O1—N2—C2	117.8 (3)	C6—C5—H5	120.07
O2—N2—C2	117.8 (3)	C1—C6—H6	119.44
C7—N1—H1	119.36	C5—C6—H6	119.56
S1—N1—H1	116.66	N1—C7—H7A	108.34
C2—C1—C6	117.9 (3)	N1—C7—H7B	108.07
S1—C1—C6	116.6 (3)	C8—C7—H7A	108.57
S1—C1—C2	125.2 (3)	C8—C7—H7B	108.80
N2—C2—C1	122.1 (3)	H7A—C7—H7B	109.32
N2—C2—C3	116.3 (3)	O6—C9—H9A	108.48
C1—C2—C3	121.6 (3)	O6—C9—H9B	109.40
C2—C3—C4	119.0 (4)	O6—C9—H9C	109.01
C3—C4—C5	120.3 (4)	H9A—C9—H9B	109.69
C4—C5—C6	120.1 (4)	H9A—C9—H9C	109.38
C1—C6—C5	121.0 (4)	H9B—C9—H9C	110.83
O3—S1—N1—C7	−138.5 (3)	O2—N2—C2—C1	139.5 (4)
O4—S1—N1—C7	−6.7 (3)	S1—C1—C2—C3	172.2 (3)
C1—S1—N1—C7	106.9 (3)	S1—C1—C6—C5	−173.7 (3)
O3—S1—C1—C2	−31.3 (3)	C6—C1—C2—N2	175.8 (3)
O3—S1—C1—C6	142.6 (3)	C6—C1—C2—C3	−1.7 (5)
O4—S1—C1—C2	−159.8 (3)	S1—C1—C2—N2	−10.3 (5)
O4—S1—C1—C6	14.1 (3)	C2—C1—C6—C5	0.7 (5)
N1—S1—C1—C2	85.8 (3)	C1—C2—C3—C4	1.6 (6)
N1—S1—C1—C6	−100.2 (3)	N2—C2—C3—C4	−176.0 (4)
C9—O6—C8—C7	−176.1 (3)	C2—C3—C4—C5	−0.5 (6)
C9—O6—C8—O5	3.1 (6)	C3—C4—C5—C6	−0.5 (6)
S1—N1—C7—C8	74.4 (4)	C4—C5—C6—C1	0.4 (6)
O1—N2—C2—C3	134.6 (4)	N1—C7—C8—O5	13.4 (5)
O1—N2—C2—C1	−43.1 (5)	N1—C7—C8—O6	−167.4 (3)
O2—N2—C2—C3	−42.9 (5)

Symmetry codes: (i) x, y+1, z; (ii) x, −y+1/2, z+1/2; (iii) x, −y+3/2, z+1/2; (iv) −x, y+1/2, −z+3/2; (v) x, −y+1/2, z−1/2; (vi) x, −y+3/2, z−1/2; (vii) −x+1, −y+1, −z+2; (viii) −x, −y+1, −z+2; (ix) −x+1, y+1/2, −z+5/2; (x) −x+1, y−1/2, −z+5/2; (xi) −x, y−1/2, −z+3/2; (xii) x, y−1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.84	2.57	3.040 (5)	116
N1—H1···O3^iii	0.84	2.13	2.941 (4)	160
C6—H6···O4	0.95	2.42	2.824 (5)	105
C7—H7A···O5^iii	0.96	2.53	3.257 (5)	133

Symmetry code: (iii) x, −y+3/2, z+1/2.