N-Allyl-N-(2-nitro­benzene­sulfonyl)-l-phenyl­alanine methyl ester

Poulsen, S.-A.; Noack, C.L.; Healy, P.C.

doi:10.1107/S160053680301256X

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N-Allyl-N-(2-nitrobenzenesulfonyl)-L-phenylalanine methyl ester

S.-A. Poulsen, C. L. Noack and P. C. Healy

The structure of the title compound, C₁₉H₂₀N₂O₆S, has been determined as part of an ongoing investigation into the preparation of bis-N-alkylated amino acids for subsequent alkene cross-metathesis reactions to generate dynamic combinatorial libraries. The overall molecular conformation is stabilized by well defined intramolecular C—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301256X/tk6115sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680301256X/tk6115Isup2.hkl Contains datablock I

CCDC reference: 217460

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.006 Å
R factor = 0.040
wR factor = 0.123
Data-to-parameter ratio = 11.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_368  Alert C Short  C(sp2)-C(sp2) Bond  C11    -   C12      =       1.16 Ang.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.50
         From the CIF: _reflns_number_total               2796
         Count of symmetry unique reflns         2637
         Completeness (_total/calc)            106.03%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       159
         Fraction of Friedel pairs measured     0.060
         Are heavy atom types Z>Si present          yes
          WARNING: Large fraction of Friedel related reflns may
                   be needed to determine absolute structure


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

Comment top

The synthesis of a range of N-allyl substituted amino acids is desirable for the investigation of the biological applications of these molecules, as cross metathesis of the allyl moieties permits a combinatorial approach to the generation of libraries for biological screening. In this approach, both protection and activation of the amino acid nitrogen is required in order to facilitate subsequent high-yielding mono-allylation. The 2-nitrobenzenesulfonyl group (oNBS) is introduced prior to allylation and serves a dual role of protection and activation with the electron withdrawing effect of the oNBS group greatly increasing the acidity of the amino hydrogen.

The title compound, (I), crystallizes in the space group P2₁2₁2₁ with one molecule in the asymmetric unit (Fig. 1). Molecules are separated by normal van der Waals distances. The bond lengths (Table 1) are in accord with conventional values (Allen et al., 1987). The conformational structure and shape of the molecules of (I) appear to be determined by a number of well defined intramolecular C—H···O interactions (Table 2) with, for example, the 2-nitrobenzenesulfonyl group 'spiralling' above the plane of the carboxylate group to bring nitro atom O2 into close proximity to the α carbon C7. It is of interest to note also in this structure, that the geometry about the amino N atom is almost trigonal planar with S1–N2–C10 = 116.7 (2)°, S1–N2–C7 = 120.5 (2)° and C7–N2–C10 = 118.8 (3)° (Σ = 355.9°).

Experimental top

Compound (I) was synthesized following published procedures (Reichwein et al. 2000). Allyl bromide (2.85 ml, 32.93 mmol) was added to a solution of 2-nitrobenzenesulfonyl-L-phenylalanine methyl ester (6.485 g, 17.8 mmol) and K₂CO₃ (4.98 g, 36.05 mmol) in anhydrous DMF (50 ml) and the mixture stirred at room temperature for 16 h. Water (40 ml) was added and the mixture extracted from ether (3 × 30 ml), the combined extracts washed with brine (3 × 40 ml) and dried over MgSO₄ before solvent was removed under reduced pressure. The resultant yellow oil afforded colourless crystals on standing. Yield: 6.51 g (90.4%); m.p. 326–327 K; ¹H NMR (CDCl₃, 200 MHz, p.p.m.): 7.54–7.85 [m, 4H, CH_arom(oNBS)], 7.18–7.28 (m, 5H, CH_aromPhe), 5.70–5.85(m, 1H, HC═), 5.07–5.28 (m, 2H, ═CH₂), 4.91 (t, 1H, J = 7.4 Hz,αCH), 3.85–4.20 (m, 2H, βCH₂), 3.55 (s, 3H, OCH₃), 3.36 (dd, 1H, ²J = 14 Hz, ³J = 7.4 Hz, NCH of NCH₂), 3.04 (dd 1H,²J = 14 Hz, ³J = 7.4 Hz, NCH of NCH₂).

Computing details top

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, 1997-2001); 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.

Figures top

Fig. 1. View of the title compound with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.

N-Allyl-N-(2-nitrobenzenesulfonyl)-L-phenylalanine methyl ester top

Crystal data top

C₁₉H₂₀N₂O₆S	F(000) = 848
M_r = 404.44	D_x = 1.344 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.2756 (15) Å	θ = 12.6–17.0°
b = 27.430 (4) Å	µ = 0.20 mm⁻¹
c = 7.8548 (12) Å	T = 295 K
V = 1998.5 (5) Å³	Prismatic, colorless
Z = 4	0.50 × 0.30 × 0.20 mm

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.025
Radiation source: Rigaku rotating anode	θ_max = 27.5°, θ_min = 2.7°
Graphite monochromator	h = −5→12
ω scans	k = 0→35
3271 measured reflections	l = −4→10
2796 independent reflections	3 standard reflections every 150 reflections
2049 reflections with I > 2σ(I)	intensity decay: 0.4%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0695P)² + 0.3341P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.123	(Δ/σ)_max = 0.035
S = 1.03	Δρ_max = 0.56 e Å⁻³
2796 reflections	Δρ_min = −0.29 e Å⁻³
254 parameters	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
0 restraints	Extinction coefficient: 0.0066 (16)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 0000 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.15 (14)

Crystal data top

C₁₉H₂₀N₂O₆S	V = 1998.5 (5) Å³
M_r = 404.44	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.2756 (15) Å	µ = 0.20 mm⁻¹
b = 27.430 (4) Å	T = 295 K
c = 7.8548 (12) Å	0.50 × 0.30 × 0.20 mm

Data collection top

Rigaku AFC-7R diffractometer	R_int = 0.025
3271 measured reflections	3 standard reflections every 150 reflections
2796 independent reflections	intensity decay: 0.4%
2049 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.123	Δρ_max = 0.56 e Å⁻³
S = 1.03	Δρ_min = −0.29 e Å⁻³
2796 reflections	Absolute structure: Flack (1983), 0000 Friedel pairs
254 parameters	Absolute structure parameter: 0.15 (14)
0 restraints

Special details top

Experimental. The scan width was (1.26 + 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 > 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 (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.01663 (8)	0.84200 (3)	0.24411 (12)	0.0509 (3)
O1	0.1434 (6)	0.77727 (15)	−0.1735 (5)	0.134 (2)
O2	0.2827 (4)	0.82963 (11)	−0.0546 (4)	0.0937 (12)
O3	−0.0051 (3)	0.85613 (8)	0.0714 (3)	0.0629 (8)
O4	−0.1049 (2)	0.83638 (9)	0.3537 (4)	0.0699 (9)
O5	0.4009 (3)	0.84493 (10)	0.3332 (4)	0.0739 (10)
O6	0.4779 (3)	0.90384 (10)	0.1574 (4)	0.0741 (10)
N1	0.2067 (4)	0.79348 (13)	−0.0523 (5)	0.0760 (14)
N2	0.1220 (3)	0.88161 (10)	0.3329 (4)	0.0497 (8)
C1	0.1051 (3)	0.78451 (11)	0.2432 (5)	0.0497 (9)
C2	0.1883 (4)	0.76690 (12)	0.1099 (5)	0.0557 (11)
C3	0.2575 (5)	0.72288 (14)	0.1207 (7)	0.0763 (14)
C4	0.2438 (5)	0.69531 (14)	0.2671 (8)	0.0880 (18)
C5	0.1564 (6)	0.71074 (16)	0.3955 (7)	0.0840 (17)
C6	0.0871 (4)	0.75482 (13)	0.3848 (5)	0.0643 (12)
C7	0.2334 (3)	0.90632 (11)	0.2334 (5)	0.0494 (9)
C8	0.3795 (3)	0.88076 (13)	0.2506 (5)	0.0563 (11)
C9	0.6213 (4)	0.8825 (2)	0.1555 (8)	0.102 (2)
C10	0.1396 (4)	0.87808 (16)	0.5190 (5)	0.0697 (14)
C11	0.0483 (6)	0.9098 (2)	0.6238 (8)	0.106 (2)
C12	−0.0369 (6)	0.9393 (2)	0.5925 (11)	0.129 (3)
C13	0.2447 (4)	0.96032 (12)	0.2792 (5)	0.0607 (13)
C14	0.1219 (3)	0.99312 (11)	0.2214 (5)	0.0524 (10)
C15	0.1210 (4)	1.04051 (13)	0.2820 (5)	0.0636 (13)
C16	0.0190 (5)	1.07375 (12)	0.2293 (6)	0.0729 (13)
C17	−0.0857 (5)	1.06013 (14)	0.1133 (7)	0.0763 (14)
C18	−0.0876 (4)	1.01278 (14)	0.0552 (6)	0.0710 (14)
C19	0.0167 (4)	0.97958 (12)	0.1064 (5)	0.0616 (11)
H3	0.31290	0.71120	0.02780	0.0930*
H4	0.29590	0.66570	0.27800	0.1110*
H5	0.14460	0.69110	0.49370	0.1030*
H6	0.02540	0.76490	0.47490	0.0780*
H7	0.20660	0.90420	0.11680	0.0610*
H11	0.06260	0.90530	0.74310	0.1280*
H15	0.19200	1.05050	0.36100	0.0790*
H16	0.02180	1.10620	0.27120	0.0900*
H17	−0.15600	1.08280	0.07640	0.0930*
H18	−0.16000	1.00260	−0.02310	0.0870*
H19	0.01590	0.94740	0.06240	0.0750*
H91	0.61370	0.84830	0.13780	0.1250*
H92	0.66830	0.88890	0.25940	0.1250*
H93	0.67510	0.89650	0.06380	0.1250*
H101	0.23750	0.88600	0.54500	0.0840*
H102	0.12090	0.84550	0.55190	0.0840*
H121	−0.05940	0.94630	0.47670	0.1600*
H122	−0.08570	0.95590	0.68120	0.1600*
H131	0.25160	0.96280	0.39870	0.0740*
H132	0.33080	0.97270	0.22810	0.0740*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0425 (4)	0.0501 (4)	0.0600 (5)	0.0024 (3)	−0.0080 (4)	0.0025 (4)
O1	0.222 (5)	0.118 (3)	0.062 (2)	−0.044 (3)	−0.016 (3)	−0.014 (2)
O2	0.113 (2)	0.086 (2)	0.082 (2)	−0.0277 (19)	0.021 (2)	0.0041 (17)
O3	0.0675 (15)	0.0527 (12)	0.0686 (15)	−0.0018 (12)	−0.0266 (15)	0.0045 (11)
O4	0.0415 (12)	0.0713 (16)	0.097 (2)	0.0031 (12)	0.0092 (14)	0.0022 (16)
O5	0.0606 (14)	0.0803 (17)	0.0807 (19)	0.0236 (14)	−0.0014 (14)	0.0164 (16)
O6	0.0441 (12)	0.0945 (19)	0.0837 (18)	0.0106 (14)	0.0081 (15)	0.0152 (16)
N1	0.102 (3)	0.069 (2)	0.057 (2)	−0.004 (2)	0.008 (2)	−0.0095 (18)
N2	0.0432 (14)	0.0523 (14)	0.0537 (16)	0.0001 (12)	−0.0019 (14)	−0.0036 (13)
C1	0.0442 (15)	0.0498 (15)	0.0552 (18)	0.0034 (13)	−0.0077 (19)	0.0044 (18)
C2	0.059 (2)	0.0510 (18)	0.057 (2)	−0.0027 (16)	−0.0014 (19)	−0.0029 (16)
C3	0.070 (2)	0.058 (2)	0.101 (3)	0.008 (2)	0.003 (3)	−0.015 (3)
C4	0.088 (3)	0.053 (2)	0.123 (4)	0.017 (2)	−0.013 (4)	0.016 (3)
C5	0.094 (3)	0.067 (3)	0.091 (3)	0.004 (2)	−0.013 (3)	0.028 (2)
C6	0.064 (2)	0.066 (2)	0.063 (2)	0.0052 (19)	0.001 (2)	0.013 (2)
C7	0.0395 (14)	0.0507 (15)	0.0579 (19)	0.0037 (12)	−0.0053 (17)	0.0024 (18)
C8	0.0477 (17)	0.0659 (19)	0.0552 (19)	0.0088 (15)	−0.003 (2)	−0.006 (2)
C9	0.046 (2)	0.152 (5)	0.109 (4)	0.023 (3)	0.009 (3)	0.007 (4)
C10	0.064 (2)	0.091 (3)	0.054 (2)	−0.007 (2)	0.001 (2)	−0.010 (2)
C11	0.077 (3)	0.136 (5)	0.105 (4)	−0.022 (3)	0.029 (3)	−0.053 (4)
C12	0.068 (3)	0.131 (5)	0.189 (7)	−0.001 (3)	0.023 (4)	−0.057 (5)
C13	0.0480 (16)	0.0551 (17)	0.079 (3)	−0.0026 (15)	−0.0101 (19)	−0.002 (2)
C14	0.0490 (16)	0.0473 (16)	0.061 (2)	−0.0027 (14)	0.0091 (18)	0.0008 (16)
C15	0.065 (2)	0.0548 (17)	0.071 (3)	−0.0050 (17)	0.001 (2)	−0.0098 (19)
C16	0.082 (2)	0.0497 (17)	0.087 (3)	0.0072 (19)	0.013 (3)	−0.008 (2)
C17	0.072 (2)	0.056 (2)	0.101 (3)	0.016 (2)	0.008 (3)	0.007 (2)
C18	0.064 (2)	0.065 (2)	0.084 (3)	0.007 (2)	−0.011 (2)	0.001 (2)
C19	0.057 (2)	0.0518 (18)	0.076 (2)	0.0070 (16)	−0.007 (2)	−0.0026 (18)

Geometric parameters (Å, º) top

S1—O3	1.425 (3)	C15—C16	1.378 (6)
S1—O4	1.427 (3)	C16—C17	1.383 (7)
S1—N2	1.619 (3)	C17—C18	1.377 (6)
S1—C1	1.778 (3)	C18—C19	1.388 (5)
O1—N1	1.204 (6)	C3—H3	0.9483
O2—N1	1.217 (5)	C4—H4	0.9490
O5—C8	1.194 (5)	C5—H5	0.9472
O6—C8	1.330 (4)	C6—H6	0.9512
O6—C9	1.453 (5)	C7—H7	0.9508
N1—C2	1.478 (5)	C9—H91	0.9510
N2—C7	1.462 (4)	C9—H92	0.9418
N2—C10	1.474 (5)	C9—H93	0.9567
C1—C2	1.388 (5)	C10—H101	0.9558
C1—C6	1.389 (5)	C10—H102	0.9463
C2—C3	1.370 (5)	C11—H11	0.9544
C3—C4	1.382 (8)	C12—H121	0.9528
C4—C5	1.361 (8)	C12—H122	0.9474
C5—C6	1.372 (6)	C13—H131	0.9433
C7—C8	1.532 (4)	C13—H132	0.9562
C7—C13	1.528 (5)	C15—H15	0.9454
C10—C11	1.467 (7)	C16—H16	0.9494
C11—C12	1.157 (8)	C17—H17	0.9465
C13—C14	1.521 (5)	C18—H18	0.9525
C14—C15	1.384 (5)	C19—H19	0.9480
C14—C19	1.381 (5)

S1···O2	3.422 (4)	C15···C11ⁱⁱⁱ	3.579 (7)
O1···O3	3.206 (5)	C16···O6^viii	3.418 (6)
O2···O3	2.938 (5)	C17···C12^x	3.504 (7)
O2···O6	3.193 (4)	C19···O3	3.403 (4)
O2···S1	3.422 (4)	C19···N2	3.368 (5)
O2···C8	2.919 (5)	C1···H102	2.9495
O2···C7	3.123 (5)	C6···H102	2.8298
O3···O2	2.938 (5)	C7···H19	2.6728
O3···O1	3.206 (5)	C8···H101	2.6651
O3···N1	2.785 (4)	C10···H131	2.7152
O3···C19	3.403 (4)	C11···H131	2.9658
O4···C9ⁱ	3.236 (5)	C12···H17^ix	2.9151
O4···C4ⁱⁱ	3.405 (7)	C13···H101	2.9188
O4···C11	3.252 (6)	C14···H131ⁱⁱⁱ	3.0436
O4···C5ⁱⁱ	3.233 (6)	C14···H121	2.9153
O5···C10	2.972 (5)	C15···H101ⁱⁱⁱ	3.0417
O5···C1	3.282 (4)	C16···H101ⁱⁱⁱ	2.9010
O5···C2	3.398 (5)	C19···H7	2.7175
O5···N2	2.776 (4)	H3···O1	2.8734
O6···C16ⁱⁱⁱ	3.418 (6)	H3···O3^xi	2.6207
O6···O2	3.193 (4)	H5···O4^vi	2.7210
O1···H3	2.8734	H5···O5ⁱⁱ	2.8169
O1···H102^iv	2.8633	H6···O4	2.4923
O2···H16ⁱⁱⁱ	2.8738	H6···H102	2.4573
O2···H7	2.5485	H7···O2	2.5485
O3···H7	2.3920	H7···O3	2.3920
O3···H19	2.5121	H7···C19	2.7175
O3···H3^v	2.6207	H7···H19	2.1715
O4···H5ⁱⁱ	2.7210	H7···H15ⁱⁱⁱ	2.5428
O4···H102	2.6216	H15···H131	2.4860
O4···H92ⁱ	2.6551	H15···H7^viii	2.5428
O4···H6	2.4923	H16···O2^viii	2.8738
O5···H101	2.5167	H17···C12^x	2.9151
O5···H91	2.5021	H19···O3	2.5121
O5···H92	2.8183	H19···C7	2.6728
O5···H5^vi	2.8169	H19···H7	2.1715
O6···H132	2.3954	H91···O5	2.5021
N1···O3	2.785 (4)	H92···O4^vii	2.6551
N2···O5	2.776 (4)	H92···O5	2.8183
N2···C19	3.368 (5)	H101···O5	2.5167
N2···H121	2.6936	H101···C8	2.6651
C1···O5	3.282 (4)	H101···C13	2.9188
C2···O5	3.398 (5)	H101···H131	2.4032
C4···O4^vi	3.405 (7)	H101···C15^viii	3.0417
C5···O4^vi	3.233 (6)	H101···C16^viii	2.9010
C6···C10	3.575 (6)	H102···O1^xii	2.8633
C7···O2	3.123 (5)	H102···O4	2.6216
C8···O2	2.919 (5)	H102···C1	2.9495
C9···O4^vii	3.236 (5)	H102···C6	2.8298
C10···C6	3.575 (6)	H102···H6	2.4573
C10···O5	2.972 (5)	H121···N2	2.6936
C11···C13	3.545 (7)	H121···C14	2.9153
C11···O4	3.252 (6)	H131···C10	2.7152
C11···C15^viii	3.579 (7)	H131···C11	2.9658
C12···C17^ix	3.504 (7)	H131···H15	2.4860
C12···C14	3.584 (9)	H131···H101	2.4032
C13···C11	3.545 (7)	H131···C14^viii	3.0436
C14···C12	3.584 (9)	H132···O6	2.3954

O3—S1—O4	119.47 (16)	C4—C3—H3	120.34
O3—S1—N2	108.23 (15)	C3—C4—H4	119.77
O3—S1—C1	107.62 (17)	C5—C4—H4	120.16
O4—S1—N2	106.83 (16)	C4—C5—H5	119.69
O4—S1—C1	105.74 (15)	C6—C5—H5	119.80
N2—S1—C1	108.56 (15)	C1—C6—H6	119.85
C8—O6—C9	116.2 (3)	C5—C6—H6	119.50
O1—N1—O2	124.9 (4)	N2—C7—H7	107.56
O1—N1—C2	116.3 (4)	C8—C7—H7	106.75
O2—N1—C2	118.8 (4)	C13—C7—H7	107.70
S1—N2—C7	120.5 (2)	O6—C9—H91	109.33
S1—N2—C10	116.7 (2)	O6—C9—H92	109.86
C7—N2—C10	118.8 (3)	O6—C9—H93	108.87
S1—C1—C2	124.7 (3)	H91—C9—H92	110.18
S1—C1—C6	117.5 (3)	H91—C9—H93	108.94
C2—C1—C6	117.8 (3)	H92—C9—H93	109.64
N1—C2—C1	122.9 (3)	N2—C10—H101	107.59
N1—C2—C3	115.7 (4)	N2—C10—H102	108.21
C1—C2—C3	121.4 (4)	C11—C10—H101	107.08
C2—C3—C4	119.4 (4)	C11—C10—H102	107.52
C3—C4—C5	120.1 (4)	H101—C10—H102	109.30
C4—C5—C6	120.5 (5)	C10—C11—H11	113.20
C1—C6—C5	120.6 (4)	C12—C11—H11	113.19
N2—C7—C8	111.5 (3)	C11—C12—H121	119.55
N2—C7—C13	111.8 (3)	C11—C12—H122	120.40
C8—C7—C13	111.2 (3)	H121—C12—H122	120.04
O5—C8—O6	125.2 (3)	C7—C13—H131	107.99
O5—C8—C7	124.9 (3)	C7—C13—H132	107.62
O6—C8—C7	109.9 (3)	C14—C13—H131	107.77
N2—C10—C11	117.0 (4)	C14—C13—H132	106.87
C10—C11—C12	133.6 (7)	H131—C13—H132	109.60
C7—C13—C14	116.9 (3)	C14—C15—H15	119.58
C13—C14—C15	117.2 (3)	C16—C15—H15	118.93
C13—C14—C19	124.4 (3)	C15—C16—H16	119.84
C15—C14—C19	118.2 (3)	C17—C16—H16	120.06
C14—C15—C16	121.5 (3)	C16—C17—H17	120.53
C15—C16—C17	120.1 (3)	C18—C17—H17	120.63
C16—C17—C18	118.8 (4)	C17—C18—H18	119.98
C17—C18—C19	120.9 (4)	C19—C18—H18	119.09
C14—C19—C18	120.4 (3)	C14—C19—H19	119.64
C2—C3—H3	120.26	C18—C19—H19	119.99

O3—S1—N2—C7	−32.1 (3)	C6—C1—C2—N1	175.4 (3)
O3—S1—N2—C10	170.5 (2)	C6—C1—C2—C3	−3.7 (5)
O4—S1—N2—C7	−161.9 (2)	C2—C1—C6—C5	3.6 (5)
O4—S1—N2—C10	40.7 (3)	S1—C1—C6—C5	−177.6 (3)
C1—S1—N2—C7	84.5 (3)	N1—C2—C3—C4	−178.9 (4)
C1—S1—N2—C10	−72.9 (3)	C1—C2—C3—C4	0.3 (6)
O3—S1—C1—C2	23.9 (3)	C2—C3—C4—C5	3.3 (7)
O3—S1—C1—C6	−154.8 (3)	C3—C4—C5—C6	−3.4 (8)
O4—S1—C1—C2	152.6 (3)	C4—C5—C6—C1	−0.2 (7)
O4—S1—C1—C6	−26.1 (3)	N2—C7—C8—O6	179.4 (3)
N2—S1—C1—C2	−93.1 (3)	N2—C7—C8—O5	0.6 (5)
N2—S1—C1—C6	88.2 (3)	C13—C7—C8—O6	−55.0 (4)
C9—O6—C8—O5	1.2 (6)	N2—C7—C13—C14	−71.4 (4)
C9—O6—C8—C7	−177.6 (4)	C8—C7—C13—C14	163.2 (3)
O2—N1—C2—C3	−107.6 (4)	C13—C7—C8—O5	126.2 (4)
O1—N1—C2—C1	−106.5 (5)	N2—C10—C11—C12	−2.0 (9)
O1—N1—C2—C3	72.7 (5)	C7—C13—C14—C15	171.3 (3)
O2—N1—C2—C1	73.3 (5)	C7—C13—C14—C19	−12.3 (5)
S1—N2—C7—C8	−95.7 (3)	C13—C14—C19—C18	−177.0 (4)
S1—N2—C7—C13	139.1 (3)	C15—C14—C19—C18	−0.7 (6)
C10—N2—C7—C8	61.3 (4)	C13—C14—C15—C16	176.2 (4)
C7—N2—C10—C11	105.9 (4)	C19—C14—C15—C16	−0.4 (6)
S1—N2—C10—C11	−96.3 (4)	C14—C15—C16—C17	0.0 (7)
C10—N2—C7—C13	−64.0 (4)	C15—C16—C17—C18	1.4 (7)
S1—C1—C2—N1	−3.2 (5)	C16—C17—C18—C19	−2.5 (7)
S1—C1—C2—C3	177.7 (3)	C17—C18—C19—C14	2.1 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4	0.95	2.49	2.870 (4)	104
C7—H7···O2	0.95	2.55	3.123 (5)	119
C7—H7···O3	0.95	2.39	2.900 (4)	113
C19—H19···O3	0.95	2.51	3.403 (4)	157
C10—H101···O5	0.96	2.52	2.972 (5)	109
C13—H132···O6	0.96	2.40	2.827 (5)	107

Experimental details

Crystal data
Chemical formula	C₁₉H₂₀N₂O₆S
M_r	404.44
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	9.2756 (15), 27.430 (4), 7.8548 (12)
V (Å³)	1998.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.50 × 0.30 × 0.20

Data collection
Diffractometer	Rigaku AFC-7R diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3271, 2796, 2049
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.123, 1.03
No. of reflections	2796
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.29
Absolute structure	Flack (1983), 0000 Friedel pairs
Absolute structure parameter	0.15 (14)

Computer programs: MSC/AFC7 Diffractometer Control Software for Windows (Molecular Structure Corporation, 1999), MSC/AFC7 Diffractometer Control Software for Windows, TEXSAN for Windows (Molecular Structure Corporation, 1997-2001), TEXSAN for Windows and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2001) and ORTEP-3 (Farrugia, 1997), TEXSAN for Windows and PLATON.

Selected geometric parameters (Å, º) top

S1—O3	1.425 (3)	O6—C9	1.453 (5)
S1—O4	1.427 (3)	N1—C2	1.478 (5)
S1—N2	1.619 (3)	N2—C7	1.462 (4)
S1—C1	1.778 (3)	N2—C10	1.474 (5)
O1—N1	1.204 (6)	C7—C13	1.528 (5)
O2—N1	1.217 (5)	C10—C11	1.467 (7)
O5—C8	1.194 (5)	C11—C12	1.157 (8)
O6—C8	1.330 (4)	C13—C14	1.521 (5)

O3—S1—O4	119.47 (16)	S1—C1—C2	124.7 (3)
O3—S1—N2	108.23 (15)	S1—C1—C6	117.5 (3)
O3—S1—C1	107.62 (17)	C2—C1—C6	117.8 (3)
O4—S1—N2	106.83 (16)	N1—C2—C1	122.9 (3)
O4—S1—C1	105.74 (15)	N1—C2—C3	115.7 (4)
N2—S1—C1	108.56 (15)	N2—C7—C8	111.5 (3)
C8—O6—C9	116.2 (3)	N2—C7—C13	111.8 (3)
O1—N1—O2	124.9 (4)	C8—C7—C13	111.2 (3)
O1—N1—C2	116.3 (4)	O5—C8—O6	125.2 (3)
O2—N1—C2	118.8 (4)	O5—C8—C7	124.9 (3)
S1—N2—C7	120.5 (2)	O6—C8—C7	109.9 (3)
S1—N2—C10	116.7 (2)	N2—C10—C11	117.0 (4)
C7—N2—C10	118.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O4	0.95	2.49	2.870 (4)	104
C7—H7···O2	0.95	2.55	3.123 (5)	119
C7—H7···O3	0.95	2.39	2.900 (4)	113
C19—H19···O3	0.95	2.51	3.403 (4)	157
C10—H101···O5	0.96	2.52	2.972 (5)	109
C13—H132···O6	0.96	2.40	2.827 (5)	107

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N-Allyl-N-(2-nitro­benzene­sulfonyl)-L-phenyl­alanine methyl ester