N-{1-[(3-Bromo-prop-yl)amino-carbon-yl]eth-yl}-2-(2-nitro-benzene-sulfonamido)propionamide.

In the title compound, C(15)H(21)BrN(4)O(6)S, all three NH groups are involved in inter-molecular N-H⋯O inter-actions which, together with two inter-molecular C-H⋯O contacts, lead to a continuous anti-parallel β-sheet structure. There are no π-π inter-actions between mol-ecules, and two C-H⋯π inter-actions primarily govern the linkage between sheets.

Related literature

For conformationally restricted peptide analogues, see: Belvisi et al. (2000 ▶); Ripka et al. (1993 ▶). For C-H⋯π inter­actions in crystals and peptides, see: Ciunik et al. (1998 ▶); Görbitz (1989 ▶); Nishio (2004 ▶); Nishio & Hirota (1989 ▶). For the correlation between peptide sequences and folds, see: Venkatraman et al. (2001 ▶); Wilmot & Thornton (1988 ▶). For bond angles in β-strand structures, see: Loughlin et al. (2004 ▶).

Experimental

Crystal data

C15H21BrN4O6S

M = 465.33

Orthorhombic,

a = 9.4467 (4) Å

b = 12.7438 (5) Å

c = 17.3257 (7) Å

V = 2085.79 (15) Å3

Z = 4

Mo Kα radiation

μ = 2.11 mm−1

T = 292 K

0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.571, T max = 0.817

33853 measured reflections

4107 independent reflections

3007 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.138

S = 1.10

4107 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.51 e Å−3

Absolute structure: Flack (1983 ▶), 1763 Friedel pairs

Flack parameter: −0.011 (13)

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034291/bg2284sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034291/bg2284Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H21BrN4O6S	Dx = 1.479 Mg m−3
Mr = 465.33	Melting point: 404 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3007 reflections
a = 9.4467 (4) Å	θ = 2.0–26.0°
b = 12.7438 (5) Å	µ = 2.11 mm−1
c = 17.3257 (7) Å	T = 292 K
V = 2085.79 (15) Å3	Needle, colourless
Z = 4	0.30 × 0.20 × 0.10 mm
F(000) = 948

Bruker SMART CCD area-detector diffractometer	4107 independent reflections
Radiation source: fine-focus sealed tube	3007 reflections with I > 2σ(I)
graphite	Rint = 0.054
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −11→11
Tmin = 0.571, Tmax = 0.817	k = −15→15
33853 measured reflections	l = −21→21

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.138	w = 1/[σ2(Fo2) + (0.08P)2] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
4107 reflections	Δρmax = 0.50 e Å−3
247 parameters	Δρmin = −0.51 e Å−3
0 restraints	Absolute structure: Flack (1983), 1763 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.011 (13)

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
Br1	0.53403 (7)	−0.37246 (5)	1.22175 (4)	0.0837 (3)
S1	0.50247 (10)	0.51539 (8)	0.93158 (6)	0.0381 (3)
C1	0.4914 (5)	0.4329 (3)	0.8477 (2)	0.0399 (9)
C4	0.4882 (8)	0.3109 (5)	0.7161 (3)	0.0774 (18)
H4	0.4882	0.2697	0.6719	0.093*
C2	0.6041 (5)	0.3690 (4)	0.8313 (3)	0.0553 (12)
H2	0.6826	0.3681	0.8637	0.066*
C6	0.3764 (5)	0.4355 (4)	0.7986 (3)	0.0436 (11)
C5	0.3759 (6)	0.3765 (4)	0.7309 (3)	0.0633 (14)
H5	0.3009	0.3815	0.6963	0.076*
C3	0.6009 (6)	0.3060 (4)	0.7667 (4)	0.0692 (16)
H3	0.6751	0.2599	0.7571	0.083*
O3	0.4231 (3)	0.6086 (2)	0.91578 (19)	0.0506 (8)
O4	0.6505 (3)	0.5244 (3)	0.9481 (2)	0.0550 (9)
O1	0.1799 (4)	0.4744 (3)	0.8693 (2)	0.0690 (10)
O2	0.2243 (5)	0.5726 (3)	0.7713 (3)	0.0828 (12)
N1	0.2509 (4)	0.5005 (4)	0.8145 (3)	0.0526 (10)
N2	0.4295 (3)	0.4562 (2)	1.0023 (2)	0.0345 (8)
H2A	0.3557	0.4835	1.0233	0.041*
C9	0.4065 (4)	0.2648 (3)	0.9969 (3)	0.0363 (9)
C7	0.4847 (4)	0.3563 (3)	1.0325 (2)	0.0335 (8)
H7	0.5856	0.3507	1.0199	0.040*
C8	0.4666 (7)	0.3526 (4)	1.1197 (3)	0.0709 (16)
H8A	0.5211	0.4078	1.1430	0.106*
H8B	0.4988	0.2860	1.1388	0.106*
H8C	0.3685	0.3617	1.1325	0.106*
O5	0.2778 (3)	0.2645 (3)	0.9909 (2)	0.0607 (10)
N3	0.4858 (3)	0.1824 (2)	0.9757 (2)	0.0362 (8)
H3A	0.5765	0.1867	0.9789	0.043*
C12	0.5198 (4)	−0.0043 (3)	0.9661 (2)	0.0383 (9)
C10	0.4212 (4)	0.0847 (3)	0.9472 (3)	0.0432 (11)
H10	0.3307	0.0735	0.9735	0.052*
C11	0.3953 (6)	0.0907 (4)	0.8584 (3)	0.0611 (14)
H11A	0.3342	0.1489	0.8471	0.092*
H11B	0.3518	0.0268	0.8411	0.092*
H11C	0.4841	0.1001	0.8323	0.092*
O6	0.6452 (3)	−0.0016 (2)	0.94723 (19)	0.0473 (8)
N4	0.4607 (4)	−0.0872 (3)	1.0009 (2)	0.0497 (9)
H4A	0.3710	−0.0865	1.0092	0.060*
C13	0.5414 (6)	−0.1783 (4)	1.0252 (3)	0.0582 (13)
H13A	0.6400	−0.1582	1.0307	0.070*
H13B	0.5362	−0.2312	0.9851	0.070*
C14	0.4926 (6)	−0.2250 (4)	1.0989 (3)	0.0663 (14)
H14A	0.3973	−0.2521	1.0924	0.080*
H14B	0.4901	−0.1712	1.1385	0.080*
C15	0.5908 (7)	−0.3138 (5)	1.1244 (3)	0.0698 (15)
H15A	0.6866	−0.2872	1.1287	0.084*
H15B	0.5905	−0.3686	1.0855	0.084*

	U11	U22	U33	U12	U13	U23
Br1	0.0935 (5)	0.0790 (5)	0.0787 (4)	−0.0189 (3)	−0.0056 (3)	0.0102 (4)
S1	0.0347 (5)	0.0326 (5)	0.0469 (6)	−0.0058 (4)	−0.0054 (4)	0.0037 (4)
C1	0.042 (2)	0.037 (2)	0.041 (2)	0.0002 (19)	0.0050 (19)	0.0055 (18)
C4	0.111 (5)	0.065 (3)	0.056 (3)	−0.004 (4)	0.031 (4)	−0.018 (3)
C2	0.049 (3)	0.053 (3)	0.064 (3)	0.003 (2)	0.013 (2)	0.002 (3)
C6	0.048 (3)	0.043 (3)	0.039 (3)	−0.006 (2)	0.0000 (18)	−0.004 (2)
C5	0.075 (4)	0.066 (3)	0.049 (3)	−0.011 (3)	0.003 (2)	−0.003 (3)
C3	0.071 (3)	0.054 (3)	0.083 (4)	0.011 (3)	0.026 (3)	−0.006 (3)
O3	0.060 (2)	0.0286 (15)	0.063 (2)	0.0015 (14)	−0.0122 (15)	0.0029 (15)
O4	0.0340 (15)	0.062 (2)	0.069 (2)	−0.0152 (15)	−0.0057 (14)	0.0093 (18)
O1	0.058 (2)	0.087 (3)	0.062 (2)	0.013 (2)	0.0060 (19)	−0.007 (2)
O2	0.097 (3)	0.073 (3)	0.078 (3)	0.020 (2)	−0.024 (2)	0.021 (3)
N1	0.052 (2)	0.059 (3)	0.047 (2)	0.0065 (19)	−0.0159 (19)	−0.008 (2)
N2	0.0293 (17)	0.0308 (17)	0.043 (2)	−0.0017 (13)	0.0021 (14)	−0.0028 (15)
C9	0.029 (2)	0.030 (2)	0.050 (3)	−0.0036 (16)	0.0025 (18)	0.0012 (19)
C7	0.0304 (19)	0.0297 (19)	0.040 (2)	0.0039 (16)	−0.0006 (17)	−0.0001 (17)
C8	0.106 (5)	0.059 (3)	0.047 (3)	0.002 (3)	−0.004 (3)	0.000 (2)
O5	0.0262 (15)	0.0428 (19)	0.113 (3)	0.0017 (13)	0.0000 (17)	−0.021 (2)
N3	0.0216 (15)	0.0293 (16)	0.058 (2)	−0.0037 (14)	−0.0016 (15)	−0.0067 (15)
C12	0.034 (2)	0.032 (2)	0.050 (2)	−0.0031 (17)	−0.0015 (17)	−0.0110 (18)
C10	0.030 (2)	0.029 (2)	0.070 (3)	−0.0064 (16)	0.003 (2)	−0.006 (2)
C11	0.075 (4)	0.049 (3)	0.059 (3)	0.000 (2)	−0.023 (3)	−0.011 (3)
O6	0.0345 (15)	0.0413 (17)	0.066 (2)	−0.0021 (13)	0.0056 (13)	−0.0032 (16)
N4	0.041 (2)	0.040 (2)	0.068 (2)	−0.0050 (16)	0.0005 (17)	0.0037 (18)
C13	0.063 (3)	0.038 (2)	0.074 (4)	0.001 (2)	0.003 (3)	−0.001 (2)
C14	0.062 (3)	0.052 (3)	0.086 (4)	−0.009 (3)	0.001 (3)	0.001 (3)
C15	0.089 (4)	0.068 (4)	0.053 (3)	−0.002 (3)	−0.004 (3)	−0.002 (3)

Br1—C15	1.921 (6)	C7—H7	0.9800
S1—O3	1.431 (3)	C8—H8A	0.9600
S1—O4	1.431 (3)	C8—H8B	0.9600
S1—N2	1.595 (3)	C8—H8C	0.9600
S1—C1	1.797 (4)	N3—C10	1.471 (5)
C1—C2	1.370 (7)	N3—H3A	0.8600
C1—C6	1.380 (6)	C12—O6	1.229 (5)
C4—C5	1.375 (8)	C12—N4	1.338 (5)
C4—C3	1.381 (9)	C12—C10	1.503 (6)
C4—H4	0.9300	C10—C11	1.560 (6)
C2—C3	1.377 (7)	C10—H10	0.9800
C2—H2	0.9300	C11—H11A	0.9600
C6—C5	1.393 (7)	C11—H11B	0.9600
C6—N1	1.473 (6)	C11—H11C	0.9600
C5—H5	0.9300	N4—C13	1.452 (6)
C3—H3	0.9300	N4—H4A	0.8600
O1—N1	1.209 (6)	C13—C14	1.482 (8)
O2—N1	1.211 (6)	C13—H13A	0.9700
N2—C7	1.472 (5)	C13—H13B	0.9700
N2—H2A	0.8600	C14—C15	1.529 (8)
C9—O5	1.220 (5)	C14—H14A	0.9700
C9—N3	1.342 (5)	C14—H14B	0.9700
C9—C7	1.513 (5)	C15—H15A	0.9700
C7—C8	1.521 (6)	C15—H15B	0.9700
O3—S1—O4	118.90 (19)	C7—C8—H8C	109.5
O3—S1—N2	108.22 (19)	H8A—C8—H8C	109.5
O4—S1—N2	107.87 (19)	H8B—C8—H8C	109.5
O3—S1—C1	107.47 (19)	C9—N3—C10	121.5 (3)
O4—S1—C1	105.4 (2)	C9—N3—H3A	119.3
N2—S1—C1	108.64 (18)	C10—N3—H3A	119.3
C2—C1—C6	119.8 (4)	O6—C12—N4	122.9 (4)
C2—C1—S1	118.1 (4)	O6—C12—C10	121.2 (4)
C6—C1—S1	122.0 (3)	N4—C12—C10	115.8 (3)
C5—C4—C3	120.3 (5)	N3—C10—C12	108.0 (3)
C5—C4—H4	119.8	N3—C10—C11	110.8 (4)
C3—C4—H4	119.8	C12—C10—C11	110.4 (4)
C1—C2—C3	119.9 (5)	N3—C10—H10	109.2
C1—C2—H2	120.1	C12—C10—H10	109.2
C3—C2—H2	120.1	C11—C10—H10	109.2
C1—C6—C5	120.6 (5)	C10—C11—H11A	109.5
C1—C6—N1	122.1 (4)	C10—C11—H11B	109.5
C5—C6—N1	117.3 (4)	H11A—C11—H11B	109.5
C4—C5—C6	118.8 (5)	C10—C11—H11C	109.5
C4—C5—H5	120.6	H11A—C11—H11C	109.5
C6—C5—H5	120.6	H11B—C11—H11C	109.5
C2—C3—C4	120.4 (5)	C12—N4—C13	122.9 (4)
C2—C3—H3	119.8	C12—N4—H4A	118.6
C4—C3—H3	119.8	C13—N4—H4A	118.6
O1—N1—O2	125.4 (5)	N4—C13—C14	114.1 (5)
O1—N1—C6	116.0 (4)	N4—C13—H13A	108.7
O2—N1—C6	118.6 (4)	C14—C13—H13A	108.7
C7—N2—S1	122.0 (3)	N4—C13—H13B	108.7
C7—N2—H2A	119.0	C14—C13—H13B	108.7
S1—N2—H2A	119.0	H13A—C13—H13B	107.6
O5—C9—N3	122.1 (4)	C13—C14—C15	111.0 (5)
O5—C9—C7	121.6 (4)	C13—C14—H14A	109.4
N3—C9—C7	116.3 (3)	C15—C14—H14A	109.4
N2—C7—C9	110.4 (3)	C13—C14—H14B	109.4
N2—C7—C8	109.9 (4)	C15—C14—H14B	109.4
C9—C7—C8	109.0 (4)	H14A—C14—H14B	108.0
N2—C7—H7	109.2	C14—C15—Br1	111.9 (4)
C9—C7—H7	109.2	C14—C15—H15A	109.2
C8—C7—H7	109.2	Br1—C15—H15A	109.2
C7—C8—H8A	109.5	C14—C15—H15B	109.2
C7—C8—H8B	109.5	Br1—C15—H15B	109.2
H8A—C8—H8B	109.5	H15A—C15—H15B	107.9
O3—S1—C1—C2	148.8 (4)	O4—S1—N2—C7	−50.8 (3)
O4—S1—C1—C2	21.1 (4)	C1—S1—N2—C7	62.9 (3)
N2—S1—C1—C2	−94.3 (4)	S1—N2—C7—C9	−95.6 (4)
O3—S1—C1—C6	−28.7 (4)	S1—N2—C7—C8	144.0 (4)
O4—S1—C1—C6	−156.4 (4)	O5—C9—C7—N2	−45.2 (5)
N2—S1—C1—C6	88.2 (4)	N3—C9—C7—N2	137.9 (4)
C6—C1—C2—C3	−1.3 (7)	O5—C9—C7—C8	75.7 (6)
S1—C1—C2—C3	−178.8 (4)	N3—C9—C7—C8	−101.3 (5)
C2—C1—C6—C5	−2.4 (7)	O5—C9—N3—C10	−2.8 (7)
S1—C1—C6—C5	175.0 (4)	C7—C9—N3—C10	174.1 (4)
C2—C1—C6—N1	178.3 (4)	C9—N3—C10—C12	−152.0 (4)
S1—C1—C6—N1	−4.3 (6)	C9—N3—C10—C11	87.0 (5)
C3—C4—C5—C6	−1.7 (8)	O6—C12—C10—N3	−52.6 (5)
C1—C6—C5—C4	3.9 (7)	N4—C12—C10—N3	130.4 (4)
N1—C6—C5—C4	−176.8 (5)	O6—C12—C10—C11	68.6 (5)
C1—C2—C3—C4	3.5 (8)	N4—C12—C10—C11	−108.4 (4)
C5—C4—C3—C2	−1.9 (9)	O6—C12—N4—C13	5.1 (7)
C1—C6—N1—O1	−67.9 (6)	C10—C12—N4—C13	−178.0 (4)
C5—C6—N1—O1	112.8 (5)	C12—N4—C13—C14	143.2 (5)
C1—C6—N1—O2	114.4 (5)	N4—C13—C14—C15	−174.7 (4)
C5—C6—N1—O2	−64.9 (6)	C13—C14—C15—Br1	177.8 (4)
O3—S1—N2—C7	179.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O6i	0.86	2.07	2.884 (4)	158
N3—H3A···O6	0.86	2.54	2.829 (4)	100
N3—H3A···O5ii	0.86	2.07	2.899 (4)	162
N4—H4A···O4i	0.86	2.35	3.165 (5)	159
C2—H2···O4	0.93	2.49	2.867 (6)	104
C7—H7···O5ii	0.98	2.34	3.193 (5)	145
C10—H10···O4i	0.98	2.51	3.431 (5)	156
C13—H13A···O6	0.97	2.46	2.802 (6)	100
C13—H13B···O3iii	0.97	2.60	3.496 (6)	154
C11—H11A···Cg	3.39	0.96	3.922 (6)	117
C11—H11B···Cgi	3.27	0.96	3.857 (6)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O6i	0.86	2.07	2.884 (4)	158
N3—H3A⋯O6	0.86	2.54	2.829 (4)	100
N3—H3A⋯O5ii	0.86	2.07	2.899 (4)	162
N4—H4A⋯O4i	0.86	2.35	3.165 (5)	159
C2—H2⋯O4	0.93	2.49	2.867 (6)	104
C7—H7⋯O5ii	0.98	2.34	3.193 (5)	145
C10—H10⋯O4i	0.98	2.51	3.431 (5)	156
C13—H13A⋯O6	0.97	2.46	2.802 (6)	100
C13—H13B⋯O3iii	0.97	2.60	3.496 (6)	154
C11—H11A⋯Cg	3.39	0.96	3.922 (6)	117
C11—H11B⋯Cgi	3.27	0.96	3.857 (6)	121

Symmetry codes: (i) ; (ii) ; (iii) . Cg is the centroid of the C1–C6 ring.