4-[(E)-(5-tert-Butyl-2-hydroxy­phen­yl)diazen­yl]benzoic acid benzene hemisolvate

Basu Baul, T.S.; Paul, A.; Tiekink, E.R.T.

doi:10.1107/S1600536810003880

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o540

doi:10.1107/S1600536810003880

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4-[(E)-(5-tert-Butyl-2-hydroxyphenyl)diazenyl]benzoic acid benzene hemisolvate

Tushar S. Basu Baul,^a ‡ Anup Paul ^a and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, North-Eastern Hill University, NEHU Permanent Campus, Umshing, Shillong 793 022, India, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 1 February 2010; accepted 1 February 2010; online 6 February 2010)

The title benzene hemisolvate, C₁₇H₁₈N₂O₃·0.5C₆H₆, features an essentially planar (the r.m.s. deviation of the non-H atoms, excluding methyl-C, is 0.071 Å) diazo molecule with an E conformation about the N=N bond, and a half-molecule of benzene disposed about a centre of inversion. The dihedral angle formed between the benzene rings of the diazo molecule is 7.69 (12)°. In the crystal, centrosymmetrically related dimers associate via the eight-membered carboxylic acid dimer synthon, {⋯HOC(=O)}₂, and these are connected into a supramolecular chain along the b axis via C—H⋯O contacts.

Related literature

For background to and motivation for the synthesis of the title compound, see: Basu Baul et al. (2010a ,b ,c ). For the structure of a related diazo compound, see: Basu Baul et al. (2008 ).

Experimental

Crystal data

C₁₇H₁₈N₂O₃·0.5C₆H₆
M_r = 337.39
Triclinic, $[P \overline 1]$
a = 6.0960 (2) Å
b = 7.3578 (3) Å
c = 20.6562 (7) Å
α = 81.326 (2)°
β = 88.992 (2)°
γ = 71.355 (2)°
V = 867.37 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.49 × 0.09 × 0.03 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.859, T_max = 1
11445 measured reflections
3053 independent reflections
1888 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.157
S = 1.08
3053 reflections
232 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3o⋯N1	0.84	1.87	2.587 (3)	142
O2—H2o⋯O1ⁱ	0.84	1.79	2.614 (3)	167
C3—H3⋯O1ⁱⁱ	0.95	2.59	3.473 (3)	155
C6—H6⋯O3ⁱⁱⁱ	0.95	2.48	3.201 (3)	133
Symmetry codes: (i) -x+2, -y+2, -z; (ii) -x+2, -y+1, -z; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003880/hg2642sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003880/hg2642Isup2.hkl

checkCIF report

Comment top

4-Aminobenzoic acid reacts with 4-tert-butyl-phenol to yield the title compound which was prepared during an on-going study of the coordination chemistry of organotin carboxylates, their potential as cytotoxic agents and molecular modelling (Basu Baul et al., 2010a,b,c). The asymmetric unit of (I) comprises a molecule of 4-[(E)-2-(5-tert-butyl-2-hydroxyphenyl)diazen-1-yl]benzoic acid and half a molecule of benzene, with the latter being disposed about a crystallographic centre of inversion. The conformation about the central N1═N2 bond [1.269 (3) Å] is E, Fig. 1. The diazo molecule is essentially planar with the exception of the tert-butyl group. The planarity is reflected in the sequence of O1–C1–C2–C3, C4–C5–N1–N2, and N1–N2–C8–C9 torsion angles of 6.4 (4), 172.6 (2), and 0.1 (4)°, respectively, which show only small twists in the molecule. The dihedral angle formed between the two benzene rings is 7.69 (12) °. The planar conformation is stabilised by an intramolecular O_hydroxyl—H···N_azo hydrogen bond, Table 1. In terms of geometric parameters, the diazo compound in (I) resembles those reported for the 2-benzoic acid isomer (Basu Baul et al., 2008).

The crystal packing features a familiar eight-membered carboxylic acid dimer synthon, Table 1. These are connected into a supramolecular chain via C–H···O contacts, Fig. 2 and Table 1. The C–H···O contacts involving the carbonyl-O2 atom lead to the formation of ten-membered {···HC₃O}₂ synthons, while those involving the hydroxyl-O3—H group are somewhat larger, i.e. 17-membered {···O_hydroxylC₂N₂C₃H···O_carbonyl···HO_{carboxylic acid}C₄H}₂, and incorporate the intramolecular six-membered {···HOC₂N₂} synthons. The supramolecular chain has a flat topology and is aligned along the b axis. Chains stack in the crystal structure to form columns with the primary interactions between them being of the type π···π: ring centroid(C2—C7)···ring centroid(C8—C13)ⁱ = 3.6637 (14) Å for i: 1+x, y, z. Interspersing these arrays are the solvent benzene molecules, Fig. 3.

Related literature top

For background to and motivation for the synthesis of the title compound, see: Basu Baul et al. (2010a,b,c). For the structure of a related diazo compound, see: Basu Baul et al. (2008).

Experimental top

The compound was prepared by reacting p-carboxybenzenediazonium chloride with 4-tert-butyl-phenol in alkaline solution under cold conditions (273–278 K) following the literature method (Basu Baul et al., 2010a). Several crystallizations from methanol yielded red plates. M.pt.: 531–533 K. Anal. Calc. for C₁₇H₁₈N₂O₃: C, 68.44; H, 6.08; N, 9.39 %. Found. 68.39; H, 6.12; N, 9.40 %. IR (KBr): 1688 ν(OCO)_asym. Single crystals suitable for an X-ray crystal-structure determination were obtained by slow evaporation of a benzene solution of the analytically pure compound and shown by crystallography to be the hemi-benzene solvate, (I).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular chain formation along the b axis in (I) mediated by O—H···O hydrogen bonds (orange dashed lines) and C—H···O contacts (blue dashed lines).
	Fig. 3. View in projection down the a axis of the crystal packing in (I), highlighting the stacking of supramolecular chains. The O—H···O hydrogen bonds are shown as orange dashed lines, and C—H···O contacts as blue dashed lines.

4-[(E)-(5-tert-Butyl-2-hydroxyphenyl)diazenyl]benzoic acid benzene hemisolvate top

Crystal data top

C₁₇H₁₈N₂O₃·0.5C₆H₆	Z = 2
M_r = 337.39	F(000) = 358
Triclinic, P1	D_x = 1.292 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0960 (2) Å	Cell parameters from 2230 reflections
b = 7.3578 (3) Å	θ = 3.0–25.1°
c = 20.6562 (7) Å	µ = 0.09 mm⁻¹
α = 81.326 (2)°	T = 100 K
β = 88.992 (2)°	Plate, orange
γ = 71.355 (2)°	0.49 × 0.09 × 0.03 mm
V = 867.37 (5) Å³

Data collection top

Bruker SMART APEXII diffractometer	3053 independent reflections
Radiation source: sealed tube	1888 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.859, T_max = 1	k = −8→8
11445 measured reflections	l = −24→24

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0815P)² + 0.0458P] where P = (F_o² + 2F_c²)/3
3053 reflections	(Δ/σ)_max = 0.001
232 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₇H₁₈N₂O₃·0.5C₆H₆	γ = 71.355 (2)°
M_r = 337.39	V = 867.37 (5) Å³
Triclinic, P1	Z = 2
a = 6.0960 (2) Å	Mo Kα radiation
b = 7.3578 (3) Å	µ = 0.09 mm⁻¹
c = 20.6562 (7) Å	T = 100 K
α = 81.326 (2)°	0.49 × 0.09 × 0.03 mm
β = 88.992 (2)°

Data collection top

Bruker SMART APEXII diffractometer	3053 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1888 reflections with I > 2σ(I)
T_min = 0.859, T_max = 1	R_int = 0.049
11445 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.08	Δρ_max = 0.25 e Å⁻³
3053 reflections	Δρ_min = −0.39 e Å⁻³
232 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.9406 (3)	0.7864 (2)	0.00097 (8)	0.0270 (5)
O2	0.7757 (3)	1.0387 (2)	0.05359 (8)	0.0270 (5)
H2O	0.8709	1.0827	0.0321	0.040*
O3	0.0159 (3)	0.2070 (2)	0.17405 (9)	0.0295 (5)
H3O	0.1019	0.2690	0.1569	0.044*
N1	0.1696 (3)	0.4998 (3)	0.15671 (9)	0.0214 (5)
N2	0.0282 (3)	0.5895 (3)	0.19601 (9)	0.0214 (5)
C1	0.7939 (4)	0.8718 (4)	0.03965 (11)	0.0200 (6)
C2	0.6296 (4)	0.7767 (3)	0.07027 (11)	0.0186 (6)
C3	0.6505 (4)	0.5880 (4)	0.06190 (11)	0.0215 (6)
H3	0.7704	0.5196	0.0362	0.026*
C4	0.4971 (4)	0.5002 (4)	0.09100 (11)	0.0224 (6)
H4	0.5120	0.3709	0.0856	0.027*
C5	0.3208 (4)	0.6011 (4)	0.12827 (11)	0.0187 (6)
C6	0.2955 (4)	0.7910 (4)	0.13581 (11)	0.0210 (6)
H6	0.1722	0.8610	0.1602	0.025*
C7	0.4513 (4)	0.8766 (4)	0.10745 (11)	0.0224 (6)
H7	0.4371	1.0055	0.1133	0.027*
C8	−0.1216 (4)	0.4932 (4)	0.22568 (11)	0.0193 (6)
C9	−0.1262 (4)	0.3104 (4)	0.21544 (12)	0.0215 (6)
C10	−0.2869 (4)	0.2363 (4)	0.24863 (12)	0.0254 (6)
H10	−0.2942	0.1134	0.2419	0.030*
C11	−0.4361 (4)	0.3394 (4)	0.29125 (12)	0.0245 (6)
H11	−0.5437	0.2849	0.3134	0.029*
C12	−0.4341 (4)	0.5213 (4)	0.30302 (11)	0.0201 (6)
C13	−0.2753 (4)	0.5933 (4)	0.26916 (12)	0.0213 (6)
H13	−0.2699	0.7169	0.2757	0.026*
C14	−0.5974 (4)	0.6396 (4)	0.35012 (12)	0.0241 (6)
C15	−0.7522 (5)	0.5308 (4)	0.38459 (13)	0.0357 (8)
H15A	−0.8514	0.5080	0.3520	0.053*
H15B	−0.8489	0.6083	0.4154	0.053*
H15C	−0.6557	0.4060	0.4085	0.053*
C16	−0.4527 (5)	0.6816 (4)	0.40241 (13)	0.0344 (7)
H16A	−0.3585	0.5590	0.4281	0.052*
H16B	−0.5559	0.7619	0.4314	0.052*
H16C	−0.3511	0.7508	0.3811	0.052*
C17	−0.7517 (5)	0.8319 (4)	0.31170 (13)	0.0307 (7)
H17A	−0.6543	0.9044	0.2899	0.046*
H17B	−0.8531	0.9088	0.3419	0.046*
H17C	−0.8462	0.8052	0.2787	0.046*
C18	0.8298 (5)	0.0370 (4)	0.45204 (13)	0.0313 (7)
H18	0.7123	0.0620	0.4192	0.038*
C19	0.9784 (5)	0.1460 (4)	0.44705 (13)	0.0305 (7)
H19	0.9640	0.2458	0.4108	0.037*
C20	1.1478 (5)	0.1084 (4)	0.49518 (13)	0.0334 (7)
H20	1.2501	0.1831	0.4920	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0223 (10)	0.0252 (10)	0.0326 (10)	−0.0054 (8)	0.0128 (8)	−0.0077 (8)
O2	0.0259 (11)	0.0235 (11)	0.0361 (11)	−0.0136 (9)	0.0103 (9)	−0.0074 (9)
O3	0.0302 (11)	0.0227 (10)	0.0384 (11)	−0.0097 (9)	0.0153 (9)	−0.0123 (9)
N1	0.0173 (11)	0.0237 (12)	0.0241 (11)	−0.0065 (10)	0.0041 (9)	−0.0067 (10)
N2	0.0183 (11)	0.0236 (12)	0.0235 (11)	−0.0074 (10)	0.0046 (9)	−0.0062 (10)
C1	0.0195 (14)	0.0191 (14)	0.0220 (14)	−0.0065 (12)	0.0018 (11)	−0.0045 (11)
C2	0.0167 (14)	0.0205 (14)	0.0185 (13)	−0.0058 (11)	0.0021 (11)	−0.0038 (11)
C3	0.0192 (14)	0.0264 (16)	0.0190 (13)	−0.0059 (12)	0.0056 (11)	−0.0071 (11)
C4	0.0219 (14)	0.0221 (15)	0.0251 (14)	−0.0075 (12)	0.0046 (11)	−0.0087 (11)
C5	0.0154 (13)	0.0229 (15)	0.0198 (13)	−0.0082 (11)	0.0025 (11)	−0.0046 (11)
C6	0.0179 (14)	0.0221 (15)	0.0224 (13)	−0.0039 (12)	0.0072 (11)	−0.0080 (11)
C7	0.0228 (15)	0.0224 (15)	0.0232 (14)	−0.0079 (12)	0.0029 (12)	−0.0060 (12)
C8	0.0175 (13)	0.0217 (14)	0.0208 (13)	−0.0094 (12)	0.0004 (11)	−0.0032 (11)
C9	0.0194 (14)	0.0222 (15)	0.0226 (14)	−0.0054 (12)	0.0022 (11)	−0.0051 (11)
C10	0.0265 (15)	0.0208 (15)	0.0316 (15)	−0.0109 (13)	0.0044 (12)	−0.0059 (12)
C11	0.0212 (15)	0.0279 (16)	0.0260 (14)	−0.0118 (12)	0.0032 (12)	−0.0012 (12)
C12	0.0168 (13)	0.0231 (15)	0.0196 (13)	−0.0054 (11)	0.0013 (11)	−0.0027 (11)
C13	0.0201 (14)	0.0218 (14)	0.0245 (14)	−0.0079 (12)	0.0023 (11)	−0.0088 (11)
C14	0.0204 (14)	0.0304 (16)	0.0239 (14)	−0.0096 (12)	0.0056 (11)	−0.0085 (12)
C15	0.0292 (16)	0.0411 (18)	0.0372 (17)	−0.0118 (14)	0.0160 (14)	−0.0081 (14)
C16	0.0270 (16)	0.0456 (19)	0.0325 (16)	−0.0092 (14)	0.0073 (13)	−0.0177 (14)
C17	0.0257 (16)	0.0315 (17)	0.0335 (16)	−0.0048 (13)	0.0096 (13)	−0.0111 (13)
C18	0.0308 (17)	0.0334 (17)	0.0301 (16)	−0.0093 (14)	0.0007 (13)	−0.0084 (13)
C19	0.0381 (17)	0.0265 (16)	0.0270 (15)	−0.0099 (14)	0.0067 (13)	−0.0055 (12)
C20	0.0365 (18)	0.0378 (18)	0.0335 (16)	−0.0199 (15)	0.0076 (14)	−0.0114 (14)

Geometric parameters (Å, º) top

O1—C1	1.265 (3)	C11—C12	1.400 (4)
O2—C1	1.274 (3)	C11—H11	0.9500
O2—H2O	0.8400	C12—C13	1.379 (3)
O3—C9	1.345 (3)	C12—C14	1.537 (3)
O3—H3O	0.8400	C13—H13	0.9500
N1—N2	1.269 (3)	C14—C15	1.526 (3)
N1—C5	1.427 (3)	C14—C16	1.533 (4)
N2—C8	1.406 (3)	C14—C17	1.534 (4)
C1—C2	1.478 (3)	C15—H15A	0.9800
C2—C3	1.390 (3)	C15—H15B	0.9800
C2—C7	1.393 (3)	C15—H15C	0.9800
C3—C4	1.379 (3)	C16—H16A	0.9800
C3—H3	0.9500	C16—H16B	0.9800
C4—C5	1.390 (3)	C16—H16C	0.9800
C4—H4	0.9500	C17—H17A	0.9800
C5—C6	1.389 (3)	C17—H17B	0.9800
C6—C7	1.376 (3)	C17—H17C	0.9800
C6—H6	0.9500	C18—C20ⁱ	1.383 (4)
C7—H7	0.9500	C18—C19	1.383 (4)
C8—C13	1.398 (3)	C18—H18	0.9500
C8—C9	1.401 (3)	C19—C20	1.379 (4)
C9—C10	1.390 (3)	C19—H19	0.9500
C10—C11	1.382 (3)	C20—C18ⁱ	1.383 (4)
C10—H10	0.9500	C20—H20	0.9500

C1—O2—H2O	109.5	C13—C12—C14	120.3 (2)
C9—O3—H3O	109.5	C11—C12—C14	123.6 (2)
N2—N1—C5	114.0 (2)	C12—C13—C8	123.2 (2)
N1—N2—C8	115.6 (2)	C12—C13—H13	118.4
O1—C1—O2	123.8 (2)	C8—C13—H13	118.4
O1—C1—C2	119.2 (2)	C15—C14—C16	108.3 (2)
O2—C1—C2	117.0 (2)	C15—C14—C17	108.6 (2)
C3—C2—C7	119.5 (2)	C16—C14—C17	109.4 (2)
C3—C2—C1	120.4 (2)	C15—C14—C12	111.9 (2)
C7—C2—C1	120.1 (2)	C16—C14—C12	109.1 (2)
C4—C3—C2	120.0 (2)	C17—C14—C12	109.44 (19)
C4—C3—H3	120.0	C14—C15—H15A	109.5
C2—C3—H3	120.0	C14—C15—H15B	109.5
C3—C4—C5	119.9 (2)	H15A—C15—H15B	109.5
C3—C4—H4	120.0	C14—C15—H15C	109.5
C5—C4—H4	120.0	H15A—C15—H15C	109.5
C6—C5—C4	120.5 (2)	H15B—C15—H15C	109.5
C6—C5—N1	123.0 (2)	C14—C16—H16A	109.5
C4—C5—N1	116.4 (2)	C14—C16—H16B	109.5
C7—C6—C5	119.2 (2)	H16A—C16—H16B	109.5
C7—C6—H6	120.4	C14—C16—H16C	109.5
C5—C6—H6	120.4	H16A—C16—H16C	109.5
C6—C7—C2	120.8 (2)	H16B—C16—H16C	109.5
C6—C7—H7	119.6	C14—C17—H17A	109.5
C2—C7—H7	119.6	C14—C17—H17B	109.5
C13—C8—C9	119.4 (2)	H17A—C17—H17B	109.5
C13—C8—N2	114.9 (2)	C14—C17—H17C	109.5
C9—C8—N2	125.7 (2)	H17A—C17—H17C	109.5
O3—C9—C10	119.3 (2)	H17B—C17—H17C	109.5
O3—C9—C8	122.4 (2)	C20ⁱ—C18—C19	120.0 (3)
C10—C9—C8	118.3 (2)	C20ⁱ—C18—H18	120.0
C11—C10—C9	120.7 (2)	C19—C18—H18	120.0
C11—C10—H10	119.6	C20—C19—C18	119.3 (3)
C9—C10—H10	119.6	C20—C19—H19	120.3
C10—C11—C12	122.3 (2)	C18—C19—H19	120.3
C10—C11—H11	118.8	C19—C20—C18ⁱ	120.7 (3)
C12—C11—H11	118.8	C19—C20—H20	119.7
C13—C12—C11	116.1 (2)	C18ⁱ—C20—H20	119.7

C5—N1—N2—C8	−179.2 (2)	N2—C8—C9—O3	−0.9 (4)
O1—C1—C2—C3	6.4 (4)	C13—C8—C9—C10	0.8 (4)
O2—C1—C2—C3	−174.6 (2)	N2—C8—C9—C10	−179.7 (2)
O1—C1—C2—C7	−173.2 (2)	O3—C9—C10—C11	−179.7 (2)
O2—C1—C2—C7	5.8 (4)	C8—C9—C10—C11	−0.8 (4)
C7—C2—C3—C4	−0.8 (4)	C9—C10—C11—C12	0.2 (4)
C1—C2—C3—C4	179.6 (2)	C10—C11—C12—C13	0.5 (4)
C2—C3—C4—C5	0.5 (4)	C10—C11—C12—C14	−179.9 (2)
C3—C4—C5—C6	0.9 (4)	C11—C12—C13—C8	−0.5 (4)
C3—C4—C5—N1	−180.0 (2)	C14—C12—C13—C8	179.9 (2)
N2—N1—C5—C6	−8.3 (3)	C9—C8—C13—C12	−0.1 (4)
N2—N1—C5—C4	172.6 (2)	N2—C8—C13—C12	−179.7 (2)
C4—C5—C6—C7	−1.8 (4)	C13—C12—C14—C15	−177.7 (2)
N1—C5—C6—C7	179.1 (2)	C11—C12—C14—C15	2.7 (4)
C5—C6—C7—C2	1.5 (4)	C13—C12—C14—C16	−57.8 (3)
C3—C2—C7—C6	−0.2 (4)	C11—C12—C14—C16	122.6 (3)
C1—C2—C7—C6	179.4 (2)	C13—C12—C14—C17	61.9 (3)
N1—N2—C8—C13	179.6 (2)	C11—C12—C14—C17	−117.7 (3)
N1—N2—C8—C9	0.1 (4)	C20ⁱ—C18—C19—C20	−0.2 (4)
C13—C8—C9—O3	179.6 (2)	C18—C19—C20—C18ⁱ	0.2 (4)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···N1	0.84	1.87	2.587 (3)	142
O2—H2o···O1ⁱⁱ	0.84	1.79	2.614 (3)	167
C3—H3···O1ⁱⁱⁱ	0.95	2.59	3.473 (3)	155
C6—H6···O3^iv	0.95	2.48	3.201 (3)	133

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₃·0.5C₆H₆
M_r	337.39
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	6.0960 (2), 7.3578 (3), 20.6562 (7)
α, β, γ (°)	81.326 (2), 88.992 (2), 71.355 (2)
V (Å³)	867.37 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.49 × 0.09 × 0.03

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.859, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	11445, 3053, 1888
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.157, 1.08
No. of reflections	3053
No. of parameters	232
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.39

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3o···N1	0.84	1.87	2.587 (3)	142
O2—H2o···O1ⁱ	0.84	1.79	2.614 (3)	167
C3—H3···O1ⁱⁱ	0.95	2.59	3.473 (3)	155
C6—H6···O3ⁱⁱⁱ	0.95	2.48	3.201 (3)	133

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

Footnotes

‡Additional correspondence author, e-mail: basubaul@hotmail.com.

Acknowledgements

The financial support of the Department of Science & Technology, New Delhi, India (grant No. SR/S1/IC-03/2005, TSBB) and the University Grants Commission, New Delhi, India, through SAP–DSA (Phase-III), are gratefully acknowledged.

References

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