Ethyl 5-bromo-3-eth­oxy­carbonyl­amino-1-benzofuran-2-carboxyl­ate

Karunakar, P.; Krishnamurthy, V.; Girija, C.R.; Krishna, V.; Vaidya, V.P.; Yamuna, A.J.

doi:10.1107/S1600536813002997

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o342

doi:10.1107/S1600536813002997

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Ethyl 5-bromo-3-ethoxycarbonylamino-1-benzofuran-2-carboxylate

Prashantha Karunakar,^a V. Krishnamurthy,^a C. R. Girija,^b ^* V. Krishna,^c V. P. Vaidya ^d and A. J. Yamuna ^d

^aDepartment of Biotechnology, PES Institute of Technology, BSK III Stg, Bangalore 560 085, India, ^bDepartment of Chemistry, SSMRV College, 4th T Block, Jayanagar, Bangalore 560 041, India, ^cDepartment of Biotechnology and Bioinformatics, Kuvempu University, Shankarghatta 577 451, India, and ^dDepartment of Chemistry, Kuvempu University, Jnana Sahyadri, Shankaraghatta 577 451, India
^*Correspondence e-mail: girija.shivakumar@rediffmail.com

(Received 17 January 2013; accepted 29 January 2013; online 6 February 2013)

In the title compound, C₁₄H₁₄BrNO₅, the ester group is disordered [occupancy ratio 0.52 (2):0.48 (2)]. The major component is nearly coplanar with the benzofuran plane, subtending a dihedral angle of 7.84 (2)°, while the amide group is twisted out of the benzofuran plane making a dihedral angle of 39.69 (2)°. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, pairs of weak C—H⋯O hydrogen bonds link the molecules into inversion dimers, which are further linked via strong N—H⋯O hydrogen bonds, generating a zigzag chain extending along [100].

Related literature

For the biological activity of benzofuran derivatives, see: Oter et al. (2007 ) & Habermann et al. (1999 ).

Experimental

Crystal data

C₁₄H₁₄BrNO₅
M_r = 356.17
Monoclinic, P 2₁ /c
a = 14.1960 (7) Å
b = 4.8050 (2) Å
c = 22.128 (1) Å
β = 90.653 (1)°
V = 1509.29 (12) Å³
Z = 4
Mo Kα radiation
μ = 2.74 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.30 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.426, T_max = 0.500
14023 measured reflections
2660 independent reflections
1969 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.102
S = 1.07
2660 reflections
223 parameters
73 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.89 (1)	2.40 (3)	2.909 (4)	117 (3)
N1—H1⋯O2ⁱ	0.89 (1)	2.27 (2)	3.021 (4)	142 (3)
C10—H10B⋯O4ⁱⁱ	0.97 (1)	2.66 (2)	3.427 (4)	135 (3)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y-1, -z+1.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813002997/hg5285sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813002997/hg5285Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813002997/hg5285Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536813002997/hg5285Isup4.cml

checkCIF report

Comment top

Benzofuran derivatives are an important class of heterocyclic compounds that are known to possess variety of biological properties. Substituted benzofurans also find their application in different field such as fluorescent sensor (Oter et al., 2007), antioxidants, brightening agents, a variety of drugs and agriculture (Habermann et al., 1999). In the title compound the ester group is nearly planar with the benzofuran plane with a dihedral angle of 7.84 (2)° while the amide group is twisted out of the benzofuran plane with a dihedral angle of 39.69 (2)°.

The crystal packing is mainly governed by intra- and inter-molecular interactions. An intra-molecular N1—H1···O4 hydrogen bond (Table 1, Figure 2) acting as conformational lock is found between carbonyl O4 and H1 atom of the amide group. The crystal structure is stabilized by inter-molecular interactions N1—H1···O2 (Table 1, Figure 3) resulting in molecular chains along a axis. The structure is further stabilised by inter-molecular C10—H10B···O4 interaction (Table 1, figure 3) resulting in the formation of centrosymmetric dimers about the inversion centers.

Related literature top

For the biological activity of benzofuran derivatives, see: Oter et al. (2007) & Habermann et al. (1999).

Experimental top

A mixture of ethyl 3-amino-5-bromobenzofuran-2-carboxylate (2.84 g, 0.01 mol), anhydrous potassium carbonate (2.76 g, 0.02 mol) and ethyl chloroformate (5 ml) in dry benzene (30 ml) was heated under reflux for 8 h. The reaction mixture was filtered and potassium salts were washed with benzene. The filtrate on removal of benzene furnished the desired compound as a yellow solid. It was recrystallized from ethanol (3 g, 84%), m.p. 93–94^oC.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labeling scheme with displacement ellipiods drawn at 50% probability level.
	Fig. 2. A view of the N-H···O intramolecular interaction (dotted lines) in the crystal structure of the title compound.
	Fig. 3. A view of the N—H···O and C—H···O interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity.

Ethyl 5-bromo-3-ethoxycarbonylamino-1-benzofuran-2-carboxylate top

Crystal data top

C₁₄H₁₄BrNO₅	F(000) = 720
M_r = 356.17	D_x = 1.567 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 570.17 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.1960 (7) Å	Cell parameters from 4262 reflections
b = 4.8050 (2) Å	θ = 2.3–23.0°
c = 22.128 (1) Å	µ = 2.74 mm⁻¹
β = 90.653 (1)°	T = 293 K
V = 1509.29 (12) Å³	Needle, pale yellow
Z = 4	0.35 × 0.30 × 0.30 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2660 independent reflections
Radiation source: fine-focus sealed tube	1969 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and ϕ scan	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
T_min = 0.426, T_max = 0.500	k = −5→3
14023 measured reflections	l = −26→26

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0427P)² + 1.449P] where P = (F_o² + 2F_c²)/3
2660 reflections	(Δ/σ)_max = 0.002
223 parameters	Δρ_max = 0.62 e Å⁻³
73 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

C₁₄H₁₄BrNO₅	V = 1509.29 (12) Å³
M_r = 356.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.1960 (7) Å	µ = 2.74 mm⁻¹
b = 4.8050 (2) Å	T = 293 K
c = 22.128 (1) Å	0.35 × 0.30 × 0.30 mm
β = 90.653 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2660 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1969 reflections with I > 2σ(I)
T_min = 0.426, T_max = 0.500	R_int = 0.029
14023 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	73 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.62 e Å⁻³
2660 reflections	Δρ_min = −0.60 e Å⁻³
223 parameters

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	Occ. (<1)
C1	0.2061 (3)	0.6782 (7)	0.72919 (15)	0.0527 (9)
C2	0.2889 (3)	0.6822 (9)	0.76285 (17)	0.0676 (11)
H2	0.2934	0.7955	0.7968	0.081*
C3	0.3644 (3)	0.5218 (10)	0.74686 (17)	0.0698 (11)
H3	0.4204	0.5228	0.7691	0.084*
C4	0.3527 (3)	0.3576 (8)	0.69566 (16)	0.0526 (9)
C5	0.2708 (2)	0.3532 (7)	0.66123 (14)	0.0439 (8)
C6	0.1954 (3)	0.5175 (7)	0.67849 (15)	0.0474 (8)
H6	0.1394	0.5185	0.6563	0.057*
C7	0.2883 (2)	0.1515 (6)	0.61445 (14)	0.0424 (8)
C8	0.3765 (2)	0.0536 (7)	0.62420 (16)	0.0508 (9)
C9	0.4290 (3)	−0.1488 (9)	0.58970 (19)	0.0630 (10)
C12	0.1724 (2)	0.2280 (7)	0.53506 (14)	0.0432 (8)
C13	0.0721 (3)	0.2372 (8)	0.44862 (16)	0.0632 (10)
H13A	0.1022	0.4094	0.4365	0.076*
H13B	0.0132	0.2823	0.4680	0.076*
C14	0.0547 (4)	0.0582 (11)	0.39524 (19)	0.0908 (15)
H14A	0.1136	0.0126	0.3768	0.136*
H14B	0.0154	0.1555	0.3667	0.136*
H14C	0.0237	−0.1096	0.4076	0.136*
N1	0.2276 (2)	0.0576 (6)	0.56904 (13)	0.0486 (7)
O1	0.41846 (17)	0.1771 (6)	0.67389 (11)	0.0614 (7)
O2	0.16059 (19)	0.4717 (5)	0.54388 (12)	0.0640 (7)
O3	0.13305 (17)	0.0840 (5)	0.48991 (10)	0.0550 (6)
O4	0.3952 (2)	−0.2753 (7)	0.54795 (14)	0.0803 (9)
Br1	0.10487 (3)	0.90618 (9)	0.754534 (18)	0.0721 (2)
O5	0.5138 (10)	−0.195 (5)	0.6161 (9)	0.081 (4)	0.52 (2)
C10	0.5720 (9)	−0.418 (4)	0.5900 (9)	0.090 (3)	0.52 (2)
H10A	0.5659	−0.5801	0.6159	0.108*	0.52 (2)
H10B	0.5444	−0.4668	0.5511	0.108*	0.52 (2)
C11	0.6683 (13)	−0.373 (5)	0.5813 (11)	0.114 (5)	0.52 (2)
H11A	0.6970	−0.5406	0.5670	0.171*	0.52 (2)
H11B	0.6974	−0.3182	0.6188	0.171*	0.52 (2)
H11C	0.6765	−0.2275	0.5519	0.171*	0.52 (2)
O5'	0.5217 (11)	−0.153 (6)	0.6020 (9)	0.080 (4)	0.48 (2)
C10'	0.5794 (10)	−0.328 (4)	0.5639 (9)	0.088 (3)	0.48 (2)
H10C	0.5601	−0.5219	0.5656	0.105*	0.48 (2)
H10D	0.5787	−0.2656	0.5223	0.105*	0.48 (2)
C11'	0.6704 (12)	−0.285 (5)	0.5926 (11)	0.109 (5)	0.48 (2)
H11D	0.7170	−0.3945	0.5724	0.163*	0.48 (2)
H11E	0.6675	−0.3409	0.6343	0.163*	0.48 (2)
H11F	0.6870	−0.0919	0.5904	0.163*	0.48 (2)
H1	0.236 (3)	−0.114 (4)	0.5551 (16)	0.066 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.068 (2)	0.044 (2)	0.0463 (19)	−0.0026 (17)	0.0021 (18)	−0.0018 (16)
C2	0.086 (3)	0.066 (3)	0.051 (2)	−0.004 (2)	−0.004 (2)	−0.0180 (19)
C3	0.071 (3)	0.080 (3)	0.057 (2)	−0.005 (2)	−0.023 (2)	−0.012 (2)
C4	0.054 (2)	0.053 (2)	0.051 (2)	−0.0006 (18)	−0.0075 (17)	−0.0055 (17)
C5	0.050 (2)	0.0392 (19)	0.0427 (17)	−0.0039 (15)	−0.0093 (15)	0.0021 (14)
C6	0.051 (2)	0.0416 (18)	0.0492 (19)	−0.0017 (16)	−0.0061 (15)	0.0027 (16)
C7	0.049 (2)	0.0352 (18)	0.0432 (18)	0.0007 (15)	−0.0098 (15)	0.0003 (14)
C8	0.048 (2)	0.051 (2)	0.053 (2)	0.0035 (17)	−0.0099 (16)	−0.0051 (17)
C9	0.054 (2)	0.063 (3)	0.071 (3)	0.010 (2)	−0.008 (2)	−0.008 (2)
C12	0.048 (2)	0.0358 (19)	0.0461 (18)	0.0001 (15)	−0.0073 (15)	−0.0025 (15)
C13	0.073 (3)	0.056 (2)	0.060 (2)	0.011 (2)	−0.026 (2)	−0.001 (2)
C14	0.116 (4)	0.096 (4)	0.060 (3)	0.015 (3)	−0.034 (3)	−0.008 (3)
N1	0.0601 (18)	0.0319 (16)	0.0532 (17)	0.0075 (13)	−0.0205 (14)	−0.0060 (13)
O1	0.0541 (15)	0.0690 (17)	0.0606 (15)	0.0056 (13)	−0.0196 (12)	−0.0128 (13)
O2	0.087 (2)	0.0361 (14)	0.0685 (16)	0.0102 (13)	−0.0289 (14)	−0.0078 (12)
O3	0.0703 (16)	0.0411 (13)	0.0530 (14)	0.0065 (12)	−0.0255 (12)	−0.0052 (11)
O4	0.0720 (19)	0.082 (2)	0.087 (2)	0.0160 (16)	−0.0124 (16)	−0.0337 (18)
Br1	0.0910 (4)	0.0599 (3)	0.0658 (3)	0.0063 (2)	0.0203 (2)	−0.0064 (2)
O5	0.051 (4)	0.102 (7)	0.089 (8)	0.024 (4)	−0.008 (4)	−0.026 (6)
C10	0.061 (4)	0.116 (8)	0.093 (7)	0.018 (5)	0.000 (5)	−0.025 (6)
C11	0.103 (8)	0.135 (12)	0.104 (9)	0.043 (7)	0.002 (7)	−0.048 (8)
O5'	0.054 (4)	0.109 (7)	0.078 (7)	0.023 (4)	−0.009 (4)	−0.027 (6)
C10'	0.064 (4)	0.114 (8)	0.086 (7)	0.037 (5)	−0.003 (5)	−0.026 (6)
C11'	0.085 (7)	0.126 (12)	0.116 (9)	0.032 (7)	0.038 (6)	−0.039 (9)

Geometric parameters (Å, º) top

C1—C6	1.369 (5)	C13—O3	1.451 (4)
C1—C2	1.385 (5)	C13—C14	1.480 (5)
C1—Br1	1.897 (4)	C13—H13A	0.9700
C2—C3	1.369 (6)	C13—H13B	0.9700
C2—H2	0.9300	C14—H14A	0.9600
C3—C4	1.389 (5)	C14—H14B	0.9600
C3—H3	0.9300	C14—H14C	0.9600
C4—O1	1.366 (4)	N1—H1	0.886 (10)
C4—C5	1.384 (5)	O5—C10	1.476 (14)
C5—C6	1.386 (5)	C10—C11	1.401 (16)
C5—C7	1.442 (4)	C10—H10A	0.9700
C6—H6	0.9300	C10—H10B	0.9700
C7—C8	1.352 (5)	C11—H11A	0.9600
C7—N1	1.392 (4)	C11—H11B	0.9600
C8—O1	1.379 (4)	C11—H11C	0.9600
C8—C9	1.448 (5)	O5'—C10'	1.451 (14)
C9—O4	1.201 (5)	C10'—C11'	1.448 (16)
C9—O5'	1.342 (15)	C10'—H10C	0.9700
C9—O5	1.350 (14)	C10'—H10D	0.9700
C12—O2	1.199 (4)	C11'—H11D	0.9600
C12—O3	1.333 (4)	C11'—H11E	0.9600
C12—N1	1.354 (4)	C11'—H11F	0.9600

C6—C1—C2	122.3 (3)	C13—C14—H14A	109.5
C6—C1—Br1	119.4 (3)	C13—C14—H14B	109.5
C2—C1—Br1	118.3 (3)	H14A—C14—H14B	109.5
C3—C2—C1	121.0 (3)	C13—C14—H14C	109.5
C3—C2—H2	119.5	H14A—C14—H14C	109.5
C1—C2—H2	119.5	H14B—C14—H14C	109.5
C2—C3—C4	116.4 (4)	C12—N1—C7	123.7 (3)
C2—C3—H3	121.8	C12—N1—H1	116 (3)
C4—C3—H3	121.8	C7—N1—H1	118 (2)
O1—C4—C5	111.7 (3)	C4—O1—C8	105.3 (3)
O1—C4—C3	125.0 (3)	C12—O3—C13	116.8 (3)
C5—C4—C3	123.3 (4)	C9—O5—C10	116.7 (14)
C4—C5—C6	119.1 (3)	C11—C10—O5	119.5 (12)
C4—C5—C7	104.7 (3)	C11—C10—H10A	107.5
C6—C5—C7	136.1 (3)	O5—C10—H10A	107.5
C1—C6—C5	117.9 (3)	C11—C10—H10B	107.5
C1—C6—H6	121.0	O5—C10—H10B	107.5
C5—C6—H6	121.0	H10A—C10—H10B	107.0
C8—C7—N1	124.6 (3)	C10—C11—H11A	109.5
C8—C7—C5	106.7 (3)	C10—C11—H11B	109.5
N1—C7—C5	128.7 (3)	H11A—C11—H11B	109.5
C7—C8—O1	111.6 (3)	C10—C11—H11C	109.5
C7—C8—C9	129.1 (3)	H11A—C11—H11C	109.5
O1—C8—C9	119.3 (3)	H11B—C11—H11C	109.5
O4—C9—O5'	122.1 (10)	C9—O5'—C10'	116.8 (15)
O4—C9—O5	126.6 (10)	C11'—C10'—O5'	99.7 (13)
O4—C9—C8	122.8 (3)	C11'—C10'—H10C	111.8
O5'—C9—C8	114.4 (11)	O5'—C10'—H10C	111.8
O5—C9—C8	110.1 (10)	C11'—C10'—H10D	111.8
O2—C12—O3	124.8 (3)	O5'—C10'—H10D	111.8
O2—C12—N1	125.5 (3)	H10C—C10'—H10D	109.6
O3—C12—N1	109.7 (3)	C10'—C11'—H11D	109.5
O3—C13—C14	107.5 (3)	C10'—C11'—H11E	109.5
O3—C13—H13A	110.2	H11D—C11'—H11E	109.5
C14—C13—H13A	110.2	C10'—C11'—H11F	109.5
O3—C13—H13B	110.2	H11D—C11'—H11F	109.5
C14—C13—H13B	110.2	H11E—C11'—H11F	109.5
H13A—C13—H13B	108.5

C6—C1—C2—C3	−0.5 (6)	C7—C8—C9—O5'	164.7 (13)
Br1—C1—C2—C3	179.9 (3)	O1—C8—C9—O5'	−13.8 (13)
C1—C2—C3—C4	−0.1 (6)	C7—C8—C9—O5	−178.0 (12)
C2—C3—C4—O1	−177.6 (4)	O1—C8—C9—O5	3.5 (13)
C2—C3—C4—C5	0.7 (6)	O2—C12—N1—C7	−9.0 (6)
O1—C4—C5—C6	177.7 (3)	O3—C12—N1—C7	170.8 (3)
C3—C4—C5—C6	−0.8 (6)	C8—C7—N1—C12	−138.4 (4)
O1—C4—C5—C7	0.1 (4)	C5—C7—N1—C12	45.2 (5)
C3—C4—C5—C7	−178.3 (4)	C5—C4—O1—C8	−0.3 (4)
C2—C1—C6—C5	0.4 (5)	C3—C4—O1—C8	178.2 (4)
Br1—C1—C6—C5	−180.0 (2)	C7—C8—O1—C4	0.3 (4)
C4—C5—C6—C1	0.2 (5)	C9—C8—O1—C4	179.1 (3)
C7—C5—C6—C1	176.8 (4)	O2—C12—O3—C13	0.4 (5)
C4—C5—C7—C8	0.1 (4)	N1—C12—O3—C13	−179.4 (3)
C6—C5—C7—C8	−176.9 (4)	C14—C13—O3—C12	167.0 (4)
C4—C5—C7—N1	177.0 (3)	O4—C9—O5—C10	2 (2)
C6—C5—C7—N1	0.1 (6)	O5'—C9—O5—C10	−78 (7)
N1—C7—C8—O1	−177.4 (3)	C8—C9—O5—C10	173.7 (11)
C5—C7—C8—O1	−0.3 (4)	C9—O5—C10—C11	136 (2)
N1—C7—C8—C9	4.1 (6)	O4—C9—O5'—C10'	−3 (2)
C5—C7—C8—C9	−178.8 (4)	O5—C9—O5'—C10'	109 (8)
C7—C8—C9—O4	−5.6 (7)	C8—C9—O5'—C10'	−173.0 (13)
O1—C8—C9—O4	175.9 (4)	C9—O5'—C10'—C11'	−178 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.89 (1)	2.40 (3)	2.909 (4)	117 (3)
N1—H1···O2ⁱ	0.89 (1)	2.27 (2)	3.021 (4)	142 (3)
C10—H10B···O4ⁱⁱ	0.97 (1)	2.66 (2)	3.427 (4)	135 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄BrNO₅
M_r	356.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	14.1960 (7), 4.8050 (2), 22.128 (1)
β (°)	90.653 (1)
V (Å³)	1509.29 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.74
Crystal size (mm)	0.35 × 0.30 × 0.30

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.426, 0.500
No. of measured, independent and observed [I > 2σ(I)] reflections	14023, 2660, 1969
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.102, 1.07
No. of reflections	2660
No. of parameters	223
No. of restraints	73
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.60

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.89 (1)	2.40 (3)	2.909 (4)	117 (3)
N1—H1···O2ⁱ	0.886 (10)	2.27 (2)	3.021 (4)	142 (3)
C10—H10B···O4ⁱⁱ	0.970 (10)	2.66 (2)	3.427 (4)	135 (3)

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

Acknowledgements

The authors thank the Sophisticated Analytical Instrument Facility (SAIF), Indian Institute of Technology (IIT), Chennai, India, for the data collection. PK and CRG also thank the Rashtriya Sikshana Samithi Trust (RSST) and the Principal, Sri Sivananda Sarma Memorial Rashtriya Vidyalaya (SSMRV) College, Bangalore, for their constant support and encouragement in carrying out this work.

References

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