N-{1-[(3-Bromo­prop­yl)amino­carbon­yl]eth­yl}-2-(2-nitro­benzene­sulfonamido)propionamide

Thirupathi, R.; Reddy, D.N.; Brinda, S.; Prabhakaran, E.N.

doi:10.1107/S1600536809034291

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages o2308-o2309

doi:10.1107/S1600536809034291

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N-{1-[(3-Bromopropyl)aminocarbonyl]ethyl}-2-(2-nitrobenzenesulfonamido)propionamide

Ravula Thirupathi,^a Damodara N. Reddy,^a S. Brinda ^b and Erode N. Prabhakaran ^a ^*

^aDepartment of Organic Chemistry, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India
^*Correspondence e-mail: eprabhak@orgchem.iisc.ernet.in

(Received 24 July 2009; accepted 27 August 2009; online 5 September 2009)

In the title compound, C₁₅H₂₁BrN₄O₆S, all three NH groups are involved in intermolecular N—H⋯O interactions which, together with two intermolecular C—H⋯O contacts, lead to a continuous antiparallel β-sheet structure. There are no π–π interactions between molecules, and two C—H⋯π interactions 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_r = 465.33
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.138
S = 1.10
4107 reflections
247 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.51 e Å⁻³
Absolute structure: Flack (1983 ), 1763 Friedel pairs
Flack parameter: −0.011 (13)

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) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iii) x, y-1, z. Cg is the centroid of the C1–C6 ring.

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 ).

Supporting information

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

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

checkCIF report

Comment top

The title compound is a precursor for making conformationally restricted dipeptide analogues, which are essential for many molecular recognition events including interactions between antigens and antibodies, peptide hormones and their receptors, and enzymes and their corresponding substrates (Ripka et al., 1993; Belvisi et al., 2000). The dipeptide sequence Ala-Ala has a low frequency of appearance in the conformationally ordered regions of polypeptides (Wilmot & Thornton, 1988; Venkatraman et al., 2001). The sulfonamide group is known to render conformational ordering in peptides and many sulfonamides are crystalline in nature. The title compound was synthesized to investigate the ordering rendered to Ala-Ala dipeptide by the N-nosyl (2-nitro-benzenesulfonylamino) protecting group. In the crystal structure all the three NH groups of the molecule are involved in intermolecular N—H···O interactions.

The two adjacent amide N-H bonds, N₃—H₃ and N₄—H₄, that flank the C- terminal alanine in the title compound are antiperiplanar to each other. The phi, psi angles for the C-terminal alanine are phi = -151.9 (5)°, psi = 130.4 (2)°. These angles and the H3-N3-N4-H4 dihedral angle (166.1 (3)°) are within the limits of those found in b-strand structures (Loughlin et al., 2004). On the other hand, the two adjacent N-H bonds N₂—H₂ and N₃—H₃ that flank the N-terminal alanine are slightly distorted away from ideal antiperiplanarity (H2-N2-N3-H3 dihedral angle = 150.2 (5)°). The phi, psi angles for the N-terminal alanine are phi = 95.6 (2)°, psi = 137.8 (7)°. The distortion from the ideal phi value for a beta-strand near N2 is probably due to the fact that N2 is bonded to a sulfonyl group rather than an acyl group.

The strands are arranged in a head-to-tail fashion, with three intermolecular N—H···O interactions and two intermolecular C—H···O interactions (Table 1). These interactions are between adjacent strands and assist in forming a continuous beta-sheet structure. The C1—S1—N2—C7 torsion angle is 62.9 (3)°. This orients the phenyl ring at a dihedral angle of 73.9 (1)° from the mean plane of the rest of the molecule. The crystal structure is stabilized by two C—H···π interactions. One is intermolecular (C₁₁—C_g = 3.85 A°, Cg: the centroid of the phenyl ring) and the other is intramolecular (C₁₁—C_g = 3.92 A°). There are no π–π interactions between the phenyl rings and the interactions between the sheets are solely governed by the C—H···π interactions.

Related literature top

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 top

To a stirring solution of 2-[2'-(2-nitrosulfonylamido)-propionamido]-propanoic acid (650 mg, 1.88 mmol) in THF (10 ml) at 258 K was added N-methyl morpholene (0.31 ml, 2.82 mmol) followed by ethylchloroformate (0.18 ml,1.93 mmol) under N₂ atmosphere. After two minutes a solution of 3-bromopropan-1-ammonium bromide (536 mg, 2.44 mmol) and N-Methyl morpholene (0.51 ml, 4.7 mmol) in a mixture of DMF/THF (1.5/3 ml) were added to the mixture and stirred for 10 min. The reaction mixture was warmed to room temperature and stirred for further 8 h. THF was removed under reduced pressure and the resulting residue was diluted with EtOAc (10 ml) and washed with saturated aqueous citric acid solution (5 ml), saturated aqueous NaHCO₃ (5 ml) solution and dried (anhydrous Na₂SO₄). The solvent was removed under reduced pressure and the resulting residue was purified by silica gel flash column chromatography (EtOAc/Hexane:1/2) to obtain the title compound as a colorless solid 392 mg (0.84 mmol, 45%) (m.p. 404 K). Needle like crystals were obtained for the isolated compound by slow evaporation at room temperature from a solution in 2-propanol (2.1 mM).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 2. Packing diagram of (I). The dotted lines indicate intermolecular C—H···O and N—H···O interactions.

N-{1-[(3-Bromopropyl)aminocarbonyl]ethyl}-2-(2- nitrobenzenesulfonamido)propionamide top

Crystal data top

C₁₅H₂₁BrN₄O₆S	D_x = 1.479 Mg m⁻³
M_r = 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

Data collection top

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

Refinement top

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(F_o²) + (0.08P)²] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
4107 reflections	Δρ_max = 0.50 e Å⁻³
247 parameters	Δρ_min = −0.51 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1763 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.011 (13)

Crystal data top

C₁₅H₂₁BrN₄O₆S	V = 2085.79 (15) Å³
M_r = 465.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.4467 (4) Å	µ = 2.11 mm⁻¹
b = 12.7438 (5) Å	T = 292 K
c = 17.3257 (7) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4107 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	3007 reflections with I > 2σ(I)
T_min = 0.571, T_max = 0.817	R_int = 0.054
33853 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.138	Δρ_max = 0.50 e Å⁻³
S = 1.10	Δρ_min = −0.51 e Å⁻³
4107 reflections	Absolute structure: Flack (1983), 1763 Friedel pairs
247 parameters	Absolute structure parameter: −0.011 (13)
0 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x−1/2, −y+1/2, −z+2; (ii) x+1/2, −y+1/2, −z+2; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₂₁BrN₄O₆S
M_r	465.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	292
a, b, c (Å)	9.4467 (4), 12.7438 (5), 17.3257 (7)
V (Å³)	2085.79 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.11
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.571, 0.817
No. of measured, independent and observed [I > 2σ(I)] reflections	33853, 4107, 3007
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.138, 1.10
No. of reflections	4107
No. of parameters	247
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.51
Absolute structure	Flack (1983), 1763 Friedel pairs
Absolute structure parameter	−0.011 (13)

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O6ⁱ	0.8600	2.0700	2.884 (4)	158.00
N3—H3A···O6	0.8600	2.5400	2.829 (4)	100.00
N3—H3A···O5ⁱⁱ	0.8600	2.0700	2.899 (4)	162.00
N4—H4A···O4ⁱ	0.8600	2.3500	3.165 (5)	159.00
C2—H2···O4	0.9300	2.4900	2.867 (6)	104.00
C7—H7···O5ⁱⁱ	0.9800	2.3400	3.193 (5)	145.00
C10—H10···O4ⁱ	0.9800	2.5100	3.431 (5)	156.00
C13—H13A···O6	0.9700	2.4600	2.802 (6)	100.00
C13—H13B···O3ⁱⁱⁱ	0.9700	2.6000	3.496 (6)	154.00
C11—H11A···Cg	3.391	0.960	3.922 (6)	117
C11—H11B···Cgⁱ	3.270	0.960	3.857 (6)	121

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

Acknowledgements

The authors are grateful to Professor T. N. Guru Row for valuable discussions and for allowing access to the CCD facility, IISc, Bangalore. RT and DNR thank the CSIR for their Junior Research Fellowships.

References

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Volume 65| Part 10| October 2009| Pages o2308-o2309

doi:10.1107/S1600536809034291

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-{1-[(3-Bromo­prop­yl)amino­carbon­yl]eth­yl}-2-(2-nitro­benzene­sulfonamido)propionamide

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Experimental

Crystal data

Data collection

Refinement

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References

organic compounds

N-{1-[(3-Bromopropyl)aminocarbonyl]ethyl}-2-(2-nitrobenzenesulfonamido)propionamide