2-{2-[3-(1H-Benzimidazol-2-yl)quinolin-2-yl­oxy]eth­oxy}ethanol

Rominger, F.; Malathi, M.; Mohan, P.S.; Ramamurthi Dondeti, T.; Hashmi, A.S.K.

doi:10.1107/S1600536809002797

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o401

doi:10.1107/S1600536809002797

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2-{2-[3-(1H-Benzimidazol-2-yl)quinolin-2-yloxy]ethoxy}ethanol

Frank Rominger,^a Mahalingam Malathi,^b Palathurai Subramaniam Mohan,^b Tanuja Ramamurthi Dondeti ^a and A. Stephen K. Hashmi ^a ^*

^aOrganisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany, and ^bDepartment of Chemistry, Bharathiar University, Coimbatore 641 046, India
^*Correspondence e-mail: hashmi@hashmi.de

(Received 16 December 2008; accepted 22 January 2009; online 28 January 2009)

In the title compound, C₂₀H₁₉N₃O₃, the interplanar angle between the benzimidazole unit and the quinoline unit is 25.1 (2)°. Two different hydrogen bonds involving the hydroxy group and the imidazole unit are present. An intramolecular N—H⋯O hydrogen bond links the hydroxy group of the side chain with the imidazole unit, forming a 12-membered ring, and an intermolecular O—H⋯N hydrogen bond links the molecules, forming chains in the crystallographic b direction.

Related literature

A closely related structure is reported in the previous paper, see: Rominger et al. (2009 ). An analogous pyridine compound is essentially flat (Kim et al., 2005 ).

Experimental

Crystal data

C₂₀H₁₉N₃O₃
M_r = 349.38
Monoclinic, P 2₁ /c
a = 11.9478 (2) Å
b = 13.1338 (1) Å
c = 12.4031 (2) Å
β = 118.744 (1)°
V = 1706.47 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 200 (2) K
0.43 × 0.28 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b ) T_min = 0.960, T_max = 0.983
16400 measured reflections
3920 independent reflections
2890 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.112
S = 1.02
3920 reflections
243 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N14—H14⋯O37	0.92 (2)	2.04 (2)	2.797 (2)	138.3 (19)
O37—H37⋯N13ⁱ	0.94 (3)	1.83 (3)	2.765 (2)	175 (2)
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008a ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002797/fj2184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002797/fj2184Isup2.hkl

checkCIF report

Related literature top

A closely related structure is reported [in this issue?] by Rominger et al. (2009). An analogous pyridine compound is essentially flat (Kim et al., 2005).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 2008a); program(s) used to refine structure: SHELXTL ( Sheldrick, 2008a); molecular graphics: SHELXTL (Sheldrick, 2008a); software used to prepare material for publication: SHELXTL (Sheldrick, 2008a).

Figures top

	Fig. 1. Thermal ellipsoid representation of the title compound with the intramolecular hydrogen bond indicated as dashed line. Displacement ellipsoids were plotted at 50% probability level.
	Fig. 2. Ball and stick representation of the hydrogen bond connected chain along the b direction. Hydrogen atoms not involved in hydrogen bonds (dashed lines) have been omitted.
	Fig. 3. Enhanced figure of the title compound with displacement ellipsoids plotted at 50% probability level.

2-{2-[3-(1H-Benzimidazol-2-yl)quinolin-2-yloxy]ethoxy}ethanol top

Crystal data top

C₂₀H₁₉N₃O₃	F(000) = 736
M_r = 349.38	D_x = 1.360 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7839 reflections
a = 11.9478 (2) Å	θ = 1.9–27.5°
b = 13.1338 (1) Å	µ = 0.09 mm⁻¹
c = 12.4031 (2) Å	T = 200 K
β = 118.744 (1)°	Polyhedron, colourless
V = 1706.47 (4) Å³	0.43 × 0.28 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3920 independent reflections
Radiation source: fine-focus sealed tube	2890 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b)	h = −15→15
T_min = 0.960, T_max = 0.983	k = −16→17
16400 measured reflections	l = −16→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0424P)² + 0.5312P] where P = (F_o² + 2F_c²)/3
3920 reflections	(Δ/σ)_max = 0.001
243 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₁₉N₃O₃	V = 1706.47 (4) Å³
M_r = 349.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9478 (2) Å	µ = 0.09 mm⁻¹
b = 13.1338 (1) Å	T = 200 K
c = 12.4031 (2) Å	0.43 × 0.28 × 0.18 mm
β = 118.744 (1)°

Data collection top

Bruker SMART CCD diffractometer	3920 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b)	2890 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.983	R_int = 0.051
16400 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.19 e Å⁻³
3920 reflections	Δρ_min = −0.18 e Å⁻³
243 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
N1	0.88443 (12)	0.06208 (10)	0.82383 (11)	0.0329 (3)
C2	0.76960 (14)	0.02903 (11)	0.79014 (13)	0.0292 (3)
C3	0.70017 (13)	0.04708 (11)	0.85560 (13)	0.0280 (3)
C4	0.76217 (14)	0.10173 (11)	0.96231 (13)	0.0296 (3)
H4	0.7203	0.1149	1.0094	0.036*
C5	0.88674 (14)	0.13885 (11)	1.00364 (13)	0.0313 (3)
C6	0.95367 (16)	0.19686 (13)	1.11232 (15)	0.0390 (4)
H6	0.9141	0.2129	1.1608	0.047*
C7	1.07435 (17)	0.22987 (14)	1.14778 (16)	0.0453 (4)
H7	1.1192	0.2679	1.2216	0.054*
C8	1.13282 (17)	0.20803 (14)	1.07591 (17)	0.0452 (4)
H8	1.2171	0.2315	1.1015	0.054*
C9	1.06998 (16)	0.15334 (13)	0.96934 (16)	0.0401 (4)
H9	1.1105	0.1396	0.9212	0.048*
C10	0.94551 (14)	0.11733 (11)	0.93079 (14)	0.0315 (3)
C12	0.56784 (13)	0.01642 (11)	0.81376 (13)	0.0276 (3)
N13	0.49537 (12)	0.06596 (9)	0.85027 (11)	0.0306 (3)
N14	0.50501 (12)	−0.06326 (9)	0.73809 (11)	0.0296 (3)
H14	0.5367 (18)	−0.1089 (15)	0.7031 (17)	0.053 (5)*
C21	0.37911 (14)	0.01587 (11)	0.79551 (13)	0.0300 (3)
C22	0.26652 (15)	0.03860 (13)	0.79847 (15)	0.0376 (4)
H22	0.2627	0.0936	0.8463	0.045*
C23	0.16163 (16)	−0.02100 (14)	0.73012 (16)	0.0427 (4)
H23	0.0837	−0.0065	0.7302	0.051*
C24	0.16696 (16)	−0.10276 (14)	0.66025 (17)	0.0442 (4)
H24	0.0926	−0.1427	0.6143	0.053*
C25	0.27764 (16)	−0.12678 (13)	0.65644 (15)	0.0395 (4)
H25	0.2813	−0.1825	0.6093	0.047*
C26	0.38342 (14)	−0.06551 (11)	0.72491 (13)	0.0296 (3)
O31	0.70752 (10)	−0.02559 (8)	0.68516 (9)	0.0339 (3)
C32	0.77582 (16)	−0.04159 (13)	0.61680 (14)	0.0381 (4)
H32A	0.8550	−0.0808	0.6669	0.046*
H32B	0.7993	0.0246	0.5951	0.046*
C33	0.68995 (17)	−0.09925 (12)	0.50313 (14)	0.0396 (4)
H33A	0.6050	−0.0662	0.4615	0.048*
H33B	0.7258	−0.0988	0.4459	0.048*
O34	0.67706 (11)	−0.20130 (8)	0.53374 (10)	0.0383 (3)
C35	0.56108 (17)	−0.24765 (13)	0.44759 (15)	0.0427 (4)
H35A	0.5703	−0.3225	0.4563	0.051*
H35B	0.5436	−0.2298	0.3634	0.051*
C36	0.44979 (17)	−0.21515 (14)	0.46430 (17)	0.0470 (4)
H36A	0.4319	−0.1422	0.4429	0.056*
H36B	0.3732	−0.2544	0.4074	0.056*
O37	0.47303 (13)	−0.23023 (9)	0.58596 (12)	0.0464 (3)
H37	0.486 (2)	−0.300 (2)	0.604 (2)	0.077 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0349 (7)	0.0330 (7)	0.0346 (7)	0.0019 (5)	0.0197 (6)	0.0033 (5)
C2	0.0315 (8)	0.0271 (7)	0.0299 (7)	0.0032 (6)	0.0157 (6)	0.0034 (6)
C3	0.0296 (8)	0.0261 (7)	0.0301 (7)	0.0030 (6)	0.0158 (6)	0.0042 (6)
C4	0.0307 (8)	0.0295 (8)	0.0315 (7)	0.0029 (6)	0.0173 (6)	0.0029 (6)
C5	0.0325 (8)	0.0282 (8)	0.0320 (8)	0.0028 (6)	0.0145 (6)	0.0048 (6)
C6	0.0402 (9)	0.0388 (9)	0.0379 (9)	−0.0041 (7)	0.0187 (7)	−0.0019 (7)
C7	0.0440 (10)	0.0421 (10)	0.0424 (9)	−0.0114 (8)	0.0148 (8)	−0.0034 (8)
C8	0.0362 (9)	0.0430 (10)	0.0527 (11)	−0.0087 (8)	0.0183 (8)	0.0033 (8)
C9	0.0367 (9)	0.0393 (9)	0.0490 (10)	−0.0004 (7)	0.0243 (8)	0.0067 (8)
C10	0.0312 (8)	0.0280 (8)	0.0354 (8)	0.0025 (6)	0.0160 (7)	0.0058 (6)
C12	0.0308 (8)	0.0264 (7)	0.0261 (7)	0.0022 (6)	0.0142 (6)	0.0038 (6)
N13	0.0304 (7)	0.0323 (7)	0.0318 (6)	−0.0010 (5)	0.0170 (5)	−0.0026 (5)
N14	0.0334 (7)	0.0249 (6)	0.0337 (7)	0.0006 (5)	0.0187 (6)	−0.0003 (5)
C21	0.0309 (8)	0.0309 (8)	0.0289 (7)	−0.0010 (6)	0.0150 (6)	0.0021 (6)
C22	0.0351 (9)	0.0420 (9)	0.0395 (8)	0.0011 (7)	0.0210 (7)	−0.0023 (7)
C23	0.0332 (9)	0.0493 (10)	0.0499 (10)	−0.0028 (8)	0.0235 (8)	0.0006 (8)
C24	0.0368 (9)	0.0440 (10)	0.0502 (10)	−0.0104 (8)	0.0196 (8)	−0.0047 (8)
C25	0.0434 (9)	0.0322 (8)	0.0438 (9)	−0.0060 (7)	0.0217 (8)	−0.0053 (7)
C26	0.0322 (8)	0.0275 (7)	0.0310 (7)	0.0004 (6)	0.0167 (6)	0.0041 (6)
O31	0.0359 (6)	0.0396 (6)	0.0318 (5)	0.0000 (5)	0.0207 (5)	−0.0043 (5)
C32	0.0433 (9)	0.0443 (9)	0.0367 (8)	0.0026 (7)	0.0272 (7)	0.0004 (7)
C33	0.0553 (10)	0.0382 (9)	0.0331 (8)	0.0045 (8)	0.0274 (8)	0.0049 (7)
O34	0.0460 (7)	0.0355 (6)	0.0343 (6)	0.0061 (5)	0.0199 (5)	0.0039 (5)
C35	0.0560 (11)	0.0388 (9)	0.0333 (8)	0.0006 (8)	0.0214 (8)	−0.0013 (7)
C36	0.0478 (10)	0.0397 (10)	0.0505 (11)	0.0007 (8)	0.0213 (9)	0.0065 (8)
O37	0.0656 (8)	0.0295 (6)	0.0596 (8)	−0.0021 (6)	0.0425 (7)	−0.0045 (6)

Geometric parameters (Å, º) top

N1—C2	1.3015 (19)	C21—C26	1.398 (2)
N1—C10	1.374 (2)	C22—C23	1.371 (2)
C2—O31	1.3532 (17)	C22—H22	0.9500
C2—C3	1.432 (2)	C23—C24	1.400 (3)
C3—C4	1.368 (2)	C23—H23	0.9500
C3—C12	1.464 (2)	C24—C25	1.382 (2)
C4—C5	1.408 (2)	C24—H24	0.9500
C4—H4	0.9500	C25—C26	1.391 (2)
C5—C10	1.414 (2)	C25—H25	0.9500
C5—C6	1.414 (2)	O31—C32	1.4472 (18)
C6—C7	1.360 (2)	C32—C33	1.491 (2)
C6—H6	0.9500	C32—H32A	0.9900
C7—C8	1.401 (3)	C32—H32B	0.9900
C7—H7	0.9500	C33—O34	1.4215 (19)
C8—C9	1.368 (2)	C33—H33A	0.9900
C8—H8	0.9500	C33—H33B	0.9900
C9—C10	1.407 (2)	O34—C35	1.417 (2)
C9—H9	0.9500	C35—C36	1.503 (3)
C12—N13	1.3248 (18)	C35—H35A	0.9900
C12—N14	1.3646 (19)	C35—H35B	0.9900
N13—C21	1.3843 (19)	C36—O37	1.411 (2)
N14—C26	1.3818 (19)	C36—H36A	0.9900
N14—H14	0.92 (2)	C36—H36B	0.9900
C21—C22	1.396 (2)	O37—H37	0.94 (3)

C2—N1—C10	118.33 (13)	C21—C22—H22	121.1
N1—C2—O31	119.41 (13)	C22—C23—C24	121.35 (16)
N1—C2—C3	124.84 (14)	C22—C23—H23	119.3
O31—C2—C3	115.75 (13)	C24—C23—H23	119.3
C4—C3—C2	116.32 (13)	C25—C24—C23	121.67 (16)
C4—C3—C12	118.51 (13)	C25—C24—H24	119.2
C2—C3—C12	125.09 (13)	C23—C24—H24	119.2
C3—C4—C5	121.31 (14)	C24—C25—C26	116.78 (15)
C3—C4—H4	119.3	C24—C25—H25	121.6
C5—C4—H4	119.3	C26—C25—H25	121.6
C4—C5—C10	117.46 (14)	N14—C26—C25	132.82 (14)
C4—C5—C6	123.21 (14)	N14—C26—C21	105.24 (13)
C10—C5—C6	119.33 (14)	C25—C26—C21	121.90 (14)
C7—C6—C5	120.36 (16)	C2—O31—C32	115.99 (12)
C7—C6—H6	119.8	O31—C32—C33	107.60 (13)
C5—C6—H6	119.8	O31—C32—H32A	110.2
C6—C7—C8	120.28 (16)	C33—C32—H32A	110.2
C6—C7—H7	119.9	O31—C32—H32B	110.2
C8—C7—H7	119.9	C33—C32—H32B	110.2
C9—C8—C7	120.81 (16)	H32A—C32—H32B	108.5
C9—C8—H8	119.6	O34—C33—C32	109.88 (13)
C7—C8—H8	119.6	O34—C33—H33A	109.7
C8—C9—C10	120.26 (16)	C32—C33—H33A	109.7
C8—C9—H9	119.9	O34—C33—H33B	109.7
C10—C9—H9	119.9	C32—C33—H33B	109.7
N1—C10—C9	119.30 (14)	H33A—C33—H33B	108.2
N1—C10—C5	121.74 (13)	C35—O34—C33	113.32 (12)
C9—C10—C5	118.95 (15)	O34—C35—C36	112.53 (14)
N13—C12—N14	112.21 (13)	O34—C35—H35A	109.1
N13—C12—C3	121.05 (13)	C36—C35—H35A	109.1
N14—C12—C3	126.73 (13)	O34—C35—H35B	109.1
C12—N13—C21	105.40 (12)	C36—C35—H35B	109.1
C12—N14—C26	107.28 (12)	H35A—C35—H35B	107.8
C12—N14—H14	127.4 (12)	O37—C36—C35	112.06 (15)
C26—N14—H14	125.3 (12)	O37—C36—H36A	109.2
N13—C21—C22	129.64 (14)	C35—C36—H36A	109.2
N13—C21—C26	109.88 (13)	O37—C36—H36B	109.2
C22—C21—C26	120.41 (14)	C35—C36—H36B	109.2
C23—C22—C21	117.88 (15)	H36A—C36—H36B	107.9
C23—C22—H22	121.1	C36—O37—H37	108.8 (14)

C10—N1—C2—O31	−179.98 (13)	N14—C12—N13—C21	0.02 (16)
C10—N1—C2—C3	0.9 (2)	C3—C12—N13—C21	−178.94 (12)
N1—C2—C3—C4	−1.2 (2)	N13—C12—N14—C26	−0.11 (16)
O31—C2—C3—C4	179.63 (13)	C3—C12—N14—C26	178.78 (13)
N1—C2—C3—C12	175.39 (14)	C12—N13—C21—C22	−176.95 (16)
O31—C2—C3—C12	−3.7 (2)	C12—N13—C21—C26	0.07 (16)
C2—C3—C4—C5	0.8 (2)	N13—C21—C22—C23	176.58 (15)
C12—C3—C4—C5	−176.08 (13)	C26—C21—C22—C23	−0.2 (2)
C3—C4—C5—C10	−0.1 (2)	C21—C22—C23—C24	0.6 (3)
C3—C4—C5—C6	179.06 (14)	C22—C23—C24—C25	−0.3 (3)
C4—C5—C6—C7	179.50 (15)	C23—C24—C25—C26	−0.3 (3)
C10—C5—C6—C7	−1.3 (2)	C12—N14—C26—C25	177.47 (16)
C5—C6—C7—C8	1.0 (3)	C12—N14—C26—C21	0.15 (15)
C6—C7—C8—C9	0.0 (3)	C24—C25—C26—N14	−176.25 (16)
C7—C8—C9—C10	−0.6 (3)	C24—C25—C26—C21	0.7 (2)
C2—N1—C10—C9	179.66 (14)	N13—C21—C26—N14	−0.14 (16)
C2—N1—C10—C5	−0.2 (2)	C22—C21—C26—N14	177.20 (13)
C8—C9—C10—N1	−179.64 (15)	N13—C21—C26—C25	−177.82 (14)
C8—C9—C10—C5	0.2 (2)	C22—C21—C26—C25	−0.5 (2)
C4—C5—C10—N1	−0.2 (2)	N1—C2—O31—C32	−0.87 (19)
C6—C5—C10—N1	−179.44 (14)	C3—C2—O31—C32	178.30 (13)
C4—C5—C10—C9	179.96 (14)	C2—O31—C32—C33	−177.84 (12)
C6—C5—C10—C9	0.7 (2)	O31—C32—C33—O34	−71.36 (16)
C4—C3—C12—N13	22.5 (2)	C32—C33—O34—C35	153.87 (13)
C2—C3—C12—N13	−154.07 (14)	C33—O34—C35—C36	−78.72 (17)
C4—C3—C12—N14	−156.31 (14)	O34—C35—C36—O37	−53.58 (19)
C2—C3—C12—N14	27.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O37	0.92 (2)	2.04 (2)	2.797 (2)	138.3 (19)
O37—H37···N13ⁱ	0.94 (3)	1.83 (3)	2.765 (2)	175 (2)

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₃O₃
M_r	349.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	11.9478 (2), 13.1338 (1), 12.4031 (2)
β (°)	118.744 (1)
V (Å³)	1706.47 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.43 × 0.28 × 0.18

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008b)
T_min, T_max	0.960, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	16400, 3920, 2890
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.112, 1.02
No. of reflections	3920
No. of parameters	243
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008a), SHELXTL ( Sheldrick, 2008a).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14···O37	0.92 (2)	2.04 (2)	2.797 (2)	138.3 (19)
O37—H37···N13ⁱ	0.94 (3)	1.83 (3)	2.765 (2)	175 (2)

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

References

Kim, H. N., Lee, H. K. & Lee, S. W. (2005). Bull. Korean Chem. Soc. 26, 892–898. CAS Google Scholar
Rominger, F., Malathi, M., Mohan, P. S., Ramamurthi Dondeti, T. & Hashmi, A. S. K. (2009). Acta Cryst. E65, o400. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008a). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008b). SADABS. University of Göttingen, Germany. Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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Volume 65| Part 2| February 2009| Page o401

doi:10.1107/S1600536809002797

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