Methyl 2-bromo-3-(4-chloro­benzene­sulfonamido)­benzoate

Ghafoor, A.Z.; Chang, B.; King, C.L.; Butcher, R.J.; Kulkarni, A.A.

doi:10.1107/S1600536812048581

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o311

doi:10.1107/S1600536812048581

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Methyl 2-bromo-3-(4-chlorobenzenesulfonamido)benzoate

Ahmad Z. Ghafoor,^a Brian Chang,^a Christopher L. King,^b Ray J. Butcher ^b and Amol A. Kulkarni ^a ^*

^aCollege of Pharmacy, Howard University, 2300 4th Street, NW, Washington, DC 20059, USA, and ^bDepartment of Chemistry, Howard University, 525 College Street, NW, Washington, DC 20059, USA
^*Correspondence e-mail: amol.kulkarni@howard.edu

(Received 5 October 2012; accepted 26 November 2012; online 31 January 2013)

In the crystal structure of the title compound, C₁₄H₁₁BrClNO₄S, the molecules form inversion dimers with R₂²(8) motifs through pairs of N—H⋯O hydrogen bonds. The benzene rings are not coplanar and subtend a dihedral angle of 66.27 (8)°. The carbomethoxy group makes a dihedral angle of 75.1 (1)° with the ring to which it is attached.

Related literature

Depending on their substitution patterns, sulfonamides display a wide array of biological activity. For their use as antimitotic, antibacterial and anti-obesity agents, see: Hu et al. (2008 ); Wydysh et al. (2009 ). For structures related to the development of novel antimicrobial agents, see: Kulkarni et al. (2012a ,b ).

Experimental

Crystal data

C₁₄H₁₁BrClNO₄S
M_r = 404.66
Monoclinic, P 2₁ /c
a = 7.9206 (2) Å
b = 9.4600 (3) Å
c = 20.0915 (6) Å
β = 94.505 (3)°
V = 1500.79 (8) Å³
Z = 4
Cu Kα radiation
μ = 6.84 mm⁻¹
T = 123 K
1.06 × 0.88 × 0.52 mm

Data collection

Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2010 ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.049, T_max = 0.198
5248 measured reflections
3012 independent reflections
2873 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.08
3012 reflections
205 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.80 (4)	2.22 (4)	2.978 (3)	158 (3)
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812048581/ds2221sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812048581/ds2221Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812048581/ds2221Isup3.cml

checkCIF report

Comment top

Depending on their substitution patterns, sulfonamides display a wide array of biological activity. These compounds have been used as antimitotic, antibacterial, anti-obesity agents. See: Hu et al. (2008); Wydysh et al. (2009). The crystal structure of the title compound has not previously been reported. The title compound was synthesized as an intermediate during our synthetic studies directed towards the development of novel antimicrobial agents (Kulkarni et al., 2012a, 2012b).

In the title compound (C₁₄H₁₁Br₁Cl₁N₁O₄S₁), the molecules form dimers through N—H···O hydrogen bonding to form R²₂(8) motifs. The two phenyl rings are not coplanar and have a dihedral angle of 66.27 (8)°. The carbomethoxy group makes a dihedral angle of 75.1 (1)° with the ring to which it is attached.

Related literature top

Depending on their substitution patterns, sulfonamides display a wide array of biological activity. For their use as antimitotic, antibacterial and anti-obesity agents, see: Hu et al. (2008); Wydysh et al. (2009). For structures related to the development of novel antimicrobial agents, see: Kulkarni et al. (2012a,b).

Experimental top

A 25 ml one-neck flask equipped with a magnetic stir bar was charged with a solution of the methyl ester (230 mg, 1.0 mmole) in CH₂Cl₂ (4.0 ml). Pyridine (604 ml, 7.5 mmole) was added. The reaction mixture was cooled at 0 °C using ice-bath for 15 minutes. 4-chlorophenylsulfonyl chloride (253 mg, 1.2 mmole) was added to the reaction mixture. The reaction mixture was slowly warmed to RT and was stirred at RT for 4 h. The crude reaction mixture was poured into a separatory funnel containing 1 N HCl (20 ml) and CH₂Cl₂ (20 ml). The layers were separated, the organic layer was washed with water (2X 20 ml) and brine (1X 20 ml). It was dried over anhydr. Na₂SO₄. The solvent was evaporated in vacuo. The orange/brown oil thus obtained was purified using silica gel flash column chromatography. Elution with 40% EA in hexanes afforded the desired sulfonamide product as pale yellow crystals. mp 121–124 °C; ¹H-NMR (CDCl₃) d 7.80 (dd, J = 8.0, 2.0 Hz, 1H), 7. 68 (dt, J = 8.0, 2.0 Hz, 1H), 7.51 (dd, J = 8.0, 2.0 Hz, 1H), 7.41–7.31 (m, 4H), 3.86 (s, 3H). ¹³C-NMR (CDCl₃) d 165.9, 139.9, 137.1, 135.5, 133.4, 129.4, 128.6, 128.0, 127.7, 125.4, 115.1, 52.6.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level for non-hydrogen atoms.
	Fig. 2. The packing view showing the hydrogen bonds network. Dashed lines indicate intermolecular N—H···O hydrogen bonds (see Table 1 for details).

Methyl 2-bromo-3-(4-chlorobenzenesulfonamido)benzoate top

Crystal data top

C₁₄H₁₁BrClNO₄S	F(000) = 808
M_r = 404.66	D_x = 1.791 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3046 reflections
a = 7.9206 (2) Å	θ = 4.4–75.7°
b = 9.4600 (3) Å	µ = 6.84 mm⁻¹
c = 20.0915 (6) Å	T = 123 K
β = 94.505 (3)°	Chunk, colorless
V = 1500.79 (8) Å³	1.06 × 0.88 × 0.52 mm
Z = 4

Data collection top

Agilent Xcalibur (Ruby, Gemini) diffractometer	3012 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2873 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 10.5081 pixels mm^-1	θ_max = 75.9°, θ_min = 4.4°
ω scans	h = −9→9
Absorption correction: analytical [CrysAlis PRO (Agilent, 2010), based on expressions derived by Clark & Reid (1995)]	k = −11→7
T_min = 0.049, T_max = 0.198	l = −24→25
5248 measured reflections

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0601P)² + 0.5274P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
3012 reflections	Δρ_max = 0.48 e Å⁻³
205 parameters	Δρ_min = −0.65 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (3)

Crystal data top

C₁₄H₁₁BrClNO₄S	V = 1500.79 (8) Å³
M_r = 404.66	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 7.9206 (2) Å	µ = 6.84 mm⁻¹
b = 9.4600 (3) Å	T = 123 K
c = 20.0915 (6) Å	1.06 × 0.88 × 0.52 mm
β = 94.505 (3)°

Data collection top

Agilent Xcalibur (Ruby, Gemini) diffractometer	3012 independent reflections
Absorption correction: analytical [CrysAlis PRO (Agilent, 2010), based on expressions derived by Clark & Reid (1995)]	2873 reflections with I > 2σ(I)
T_min = 0.049, T_max = 0.198	R_int = 0.033
5248 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.48 e Å⁻³
3012 reflections	Δρ_min = −0.65 e Å⁻³
205 parameters

Special details top

Experimental. CrysAlisPro (Agilent, 2010) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)

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	0.55830 (3)	0.29987 (2)	0.362077 (11)	0.02554 (13)
Cl1	0.01337 (10)	−0.03081 (9)	0.18862 (3)	0.0433 (2)
S1	0.23124 (6)	0.09272 (5)	0.48834 (2)	0.01812 (15)
O1	0.3147 (2)	−0.03081 (17)	0.51690 (8)	0.0235 (3)
O2	0.0901 (2)	0.15202 (17)	0.51868 (8)	0.0230 (3)
O3	0.4253 (3)	0.6005 (2)	0.27820 (9)	0.0397 (5)
O4	0.5888 (3)	0.7061 (2)	0.35913 (9)	0.0352 (5)
N1	0.3799 (3)	0.2130 (2)	0.48786 (10)	0.0193 (4)
H1A	0.466 (5)	0.177 (3)	0.4775 (17)	0.027 (8)*
C1	0.3423 (3)	0.3532 (2)	0.46643 (10)	0.0185 (4)
C2	0.4146 (3)	0.4121 (2)	0.41128 (10)	0.0186 (4)
C3	0.3853 (3)	0.5527 (2)	0.39355 (11)	0.0206 (4)
C4	0.2772 (3)	0.6340 (2)	0.42946 (12)	0.0240 (4)
H4A	0.2549	0.7294	0.4170	0.029*
C5	0.2022 (3)	0.5763 (2)	0.48325 (12)	0.0229 (4)
H5A	0.1269	0.6315	0.5070	0.027*
C6	0.2372 (3)	0.4374 (3)	0.50239 (11)	0.0208 (4)
H6A	0.1890	0.3995	0.5404	0.025*
C7	0.4666 (3)	0.6198 (2)	0.33630 (11)	0.0219 (4)
C8	0.6814 (4)	0.7813 (3)	0.31100 (14)	0.0354 (6)
H8A	0.7891	0.8150	0.3326	0.053*
H8B	0.6143	0.8621	0.2936	0.053*
H8C	0.7035	0.7177	0.2742	0.053*
C9	0.1676 (3)	0.0580 (2)	0.40362 (11)	0.0203 (4)
C10	0.2808 (3)	−0.0105 (2)	0.36475 (12)	0.0233 (4)
H10A	0.3899	−0.0373	0.3835	0.028*
C11	0.2321 (3)	−0.0390 (3)	0.29849 (12)	0.0277 (5)
H11A	0.3065	−0.0871	0.2714	0.033*
C12	0.0727 (3)	0.0038 (3)	0.27216 (12)	0.0278 (5)
C13	−0.0388 (3)	0.0736 (3)	0.31041 (13)	0.0279 (5)
H13A	−0.1467	0.1028	0.2913	0.034*
C14	0.0093 (3)	0.1003 (2)	0.37711 (12)	0.0243 (5)
H14A	−0.0659	0.1473	0.4043	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03114 (18)	0.02542 (18)	0.02113 (17)	0.00412 (8)	0.00890 (10)	0.00167 (8)
Cl1	0.0431 (4)	0.0583 (4)	0.0263 (3)	0.0072 (3)	−0.0109 (3)	−0.0104 (3)
S1	0.0171 (3)	0.0196 (3)	0.0177 (3)	0.00109 (18)	0.00194 (18)	0.00302 (17)
O1	0.0231 (8)	0.0229 (8)	0.0248 (8)	0.0032 (6)	0.0033 (6)	0.0067 (6)
O2	0.0198 (7)	0.0256 (8)	0.0242 (8)	0.0008 (6)	0.0048 (6)	0.0020 (6)
O3	0.0456 (11)	0.0525 (12)	0.0200 (8)	−0.0195 (10)	−0.0034 (8)	0.0039 (8)
O4	0.0380 (10)	0.0442 (12)	0.0223 (9)	−0.0218 (9)	−0.0036 (7)	0.0062 (7)
N1	0.0168 (9)	0.0212 (9)	0.0197 (9)	0.0014 (7)	0.0005 (7)	0.0013 (7)
C1	0.0165 (9)	0.0217 (10)	0.0165 (9)	−0.0002 (8)	−0.0034 (7)	0.0007 (8)
C2	0.0168 (9)	0.0219 (10)	0.0167 (9)	0.0008 (8)	−0.0012 (7)	−0.0017 (8)
C3	0.0189 (10)	0.0230 (10)	0.0191 (10)	−0.0012 (8)	−0.0034 (8)	0.0013 (8)
C4	0.0238 (11)	0.0201 (10)	0.0271 (11)	0.0016 (8)	−0.0042 (9)	0.0010 (8)
C5	0.0192 (10)	0.0237 (11)	0.0257 (11)	0.0024 (8)	0.0008 (8)	−0.0030 (8)
C6	0.0175 (10)	0.0248 (10)	0.0199 (10)	0.0000 (8)	0.0003 (8)	0.0000 (8)
C7	0.0226 (10)	0.0212 (10)	0.0215 (10)	0.0010 (8)	−0.0015 (8)	0.0020 (8)
C8	0.0363 (14)	0.0401 (14)	0.0296 (13)	−0.0140 (11)	0.0019 (11)	0.0088 (11)
C9	0.0208 (10)	0.0186 (10)	0.0215 (10)	−0.0017 (8)	0.0005 (8)	0.0024 (8)
C10	0.0207 (10)	0.0244 (10)	0.0243 (11)	0.0018 (8)	−0.0008 (8)	0.0013 (8)
C11	0.0286 (12)	0.0285 (11)	0.0258 (12)	0.0039 (10)	0.0019 (9)	−0.0033 (9)
C12	0.0281 (12)	0.0307 (12)	0.0238 (11)	−0.0029 (9)	−0.0042 (9)	−0.0002 (9)
C13	0.0214 (11)	0.0315 (12)	0.0297 (12)	0.0002 (9)	−0.0054 (9)	0.0010 (9)
C14	0.0206 (10)	0.0244 (11)	0.0276 (11)	0.0017 (8)	−0.0001 (9)	0.0014 (9)

Geometric parameters (Å, º) top

Br1—C2	1.892 (2)	C4—H4A	0.9500
Cl1—C12	1.738 (3)	C5—C6	1.391 (3)
S1—O2	1.4294 (16)	C5—H5A	0.9500
S1—O1	1.4397 (16)	C6—H6A	0.9500
S1—N1	1.638 (2)	C8—H8A	0.9800
S1—C9	1.767 (2)	C8—H8B	0.9800
O3—C7	1.201 (3)	C8—H8C	0.9800
O3—Br1ⁱ	3.4022 (19)	C9—C14	1.383 (3)
O4—C7	1.320 (3)	C9—C10	1.394 (3)
O4—C8	1.446 (3)	C10—C11	1.383 (3)
N1—C1	1.418 (3)	C10—H10A	0.9500
N1—H1A	0.80 (4)	C11—C12	1.390 (4)
C1—C6	1.394 (3)	C11—H11A	0.9500
C1—C2	1.402 (3)	C12—C13	1.383 (4)
C2—C3	1.392 (3)	C13—C14	1.387 (4)
C3—C4	1.393 (3)	C13—H13A	0.9500
C3—C7	1.502 (3)	C14—H14A	0.9500
C4—C5	1.386 (3)

O2—S1—O1	119.91 (10)	C1—C6—H6A	119.7
O2—S1—N1	108.45 (10)	O3—C7—O4	124.6 (2)
O1—S1—N1	104.97 (10)	O3—C7—C3	125.4 (2)
O2—S1—C9	108.08 (10)	O4—C7—C3	109.98 (19)
O1—S1—C9	108.68 (10)	O4—C8—H8A	109.5
N1—S1—C9	105.91 (10)	O4—C8—H8B	109.5
C7—O3—Br1ⁱ	134.06 (17)	H8A—C8—H8B	109.5
C7—O4—C8	117.9 (2)	O4—C8—H8C	109.5
C1—N1—S1	121.14 (16)	H8A—C8—H8C	109.5
C1—N1—H1A	118 (2)	H8B—C8—H8C	109.5
S1—N1—H1A	110 (2)	C14—C9—C10	121.5 (2)
C6—C1—C2	118.7 (2)	C14—C9—S1	119.90 (18)
C6—C1—N1	119.76 (19)	C10—C9—S1	118.60 (17)
C2—C1—N1	121.51 (19)	C11—C10—C9	119.1 (2)
C3—C2—C1	120.81 (19)	C11—C10—H10A	120.4
C3—C2—Br1	119.86 (16)	C9—C10—H10A	120.4
C1—C2—Br1	119.31 (16)	C10—C11—C12	119.1 (2)
C2—C3—C4	119.4 (2)	C10—C11—H11A	120.5
C2—C3—C7	121.8 (2)	C12—C11—H11A	120.5
C4—C3—C7	118.8 (2)	C13—C12—C11	121.9 (2)
C5—C4—C3	120.3 (2)	C13—C12—Cl1	119.4 (2)
C5—C4—H4A	119.8	C11—C12—Cl1	118.8 (2)
C3—C4—H4A	119.8	C12—C13—C14	119.0 (2)
C4—C5—C6	120.0 (2)	C12—C13—H13A	120.5
C4—C5—H5A	120.0	C14—C13—H13A	120.5
C6—C5—H5A	120.0	C9—C14—C13	119.4 (2)
C5—C6—C1	120.7 (2)	C9—C14—H14A	120.3
C5—C6—H6A	119.7	C13—C14—H14A	120.3

O2—S1—N1—C1	−47.0 (2)	C8—O4—C7—C3	−179.6 (2)
O1—S1—N1—C1	−176.30 (17)	C2—C3—C7—O3	75.4 (3)
C9—S1—N1—C1	68.80 (19)	C4—C3—C7—O3	−104.3 (3)
S1—N1—C1—C6	64.4 (3)	C2—C3—C7—O4	−105.9 (3)
S1—N1—C1—C2	−118.6 (2)	C4—C3—C7—O4	74.3 (3)
C6—C1—C2—C3	1.4 (3)	O2—S1—C9—C14	5.6 (2)
N1—C1—C2—C3	−175.7 (2)	O1—S1—C9—C14	137.26 (19)
C6—C1—C2—Br1	179.72 (16)	N1—S1—C9—C14	−110.4 (2)
N1—C1—C2—Br1	2.6 (3)	O2—S1—C9—C10	−175.16 (17)
C1—C2—C3—C4	−2.6 (3)	O1—S1—C9—C10	−43.5 (2)
Br1—C2—C3—C4	179.04 (17)	N1—S1—C9—C10	68.8 (2)
C1—C2—C3—C7	177.6 (2)	C14—C9—C10—C11	−1.2 (4)
Br1—C2—C3—C7	−0.7 (3)	S1—C9—C10—C11	179.62 (18)
C2—C3—C4—C5	1.3 (3)	C9—C10—C11—C12	1.2 (4)
C7—C3—C4—C5	−178.9 (2)	C10—C11—C12—C13	−0.3 (4)
C3—C4—C5—C6	1.2 (3)	C10—C11—C12—Cl1	179.35 (19)
C4—C5—C6—C1	−2.5 (3)	C11—C12—C13—C14	−0.6 (4)
C2—C1—C6—C5	1.2 (3)	Cl1—C12—C13—C14	179.75 (19)
N1—C1—C6—C5	178.3 (2)	C10—C9—C14—C13	0.3 (4)
Br1ⁱ—O3—C7—O4	−27.5 (4)	S1—C9—C14—C13	179.46 (18)
Br1ⁱ—O3—C7—C3	150.97 (18)	C12—C13—C14—C9	0.6 (4)
C8—O4—C7—O3	−1.0 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱⁱ	0.80 (4)	2.22 (4)	2.978 (3)	158 (3)

Symmetry code: (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁BrClNO₄S
M_r	404.66
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	7.9206 (2), 9.4600 (3), 20.0915 (6)
β (°)	94.505 (3)
V (Å³)	1500.79 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	6.84
Crystal size (mm)	1.06 × 0.88 × 0.52

Data collection
Diffractometer	Agilent Xcalibur (Ruby, Gemini) diffractometer
Absorption correction	Analytical [CrysAlis PRO (Agilent, 2010), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.049, 0.198
No. of measured, independent and observed [I > 2σ(I)] reflections	5248, 3012, 2873
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.093, 1.08
No. of reflections	3012
No. of parameters	205
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.65

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.80 (4)	2.22 (4)	2.978 (3)	158 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

AAK wishes to acknowledge Dr A. K. Wutoh, Dean of the College of Pharmacy, for the purchase of chemicals and solvents, as well as RCMI, Howard University, and CDRD, College of Pharmacy, Howard University, for their support. RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

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