2-Propoxybenzamide

Al Jasem, Y.; Hindawi, B. al; Thiemann, T.; White, F.

doi:10.1107/S1600536812033326

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages o2639-o2640

doi:10.1107/S1600536812033326

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2-Propoxybenzamide

Yosef Al Jasem,^a Bassam al Hindawi,^b Thies Thiemann ^b ^* and Fraser White ^c

^aDepartment of Chemical Engineering, United Arab Emirates University, AL Ain, Abu Dhabi, United Arab Emirates, ^bDepartment of Chemistry, United Arab Emirates University, AL Ain, Abu Dhabi, United Arab Emirates, and ^cAgilent Technologies UK Ltd, 10 Mead Road, Oxford Industrial Park, Oxford OX5 1QU, England
^*Correspondence e-mail: thies@uaeu.ac.ae

(Received 11 July 2012; accepted 23 July 2012; online 4 August 2012)

In the title molecule, C₁₀H₁₃NO₂, the amide –NH₂ group is oriented toward the propoxy substituent and an intramolecular N—H⋯O hydrogen bond is formed between the N—H group and the propoxy O atom. The benzene ring forms dihedral angles of 12.41 (2) and 3.26 (2)° with the amide and propoxy group mean planes, respectively. In the crystal, N—H⋯O hydrogen bonds order pairs of molecules with their molecular planes parallel, but at an offset of 0.73 (2) Å to each other. These pairs are ordered into two types of symmetry-related columns extended along the a axis with the mean plane of a pair in one column approximately parallel to (-122) and in the other to (-1-22). The two planes form dihedral angle of 84.40 (1)°. Overall, in a three-dimensional network, the hydrogen-bonded pairs of molecules are either located in (-1-22) or (-122) layers. In one layer, each pair is involved in four C—H⋯O contacts, twice as a donor and twice as an acceptor. Additionally, there is a short C—H⋯C contact between a benzene C—H group and the amide π-system.

Related literature

For crystal structures of similar compounds, see: Pagola & Stephens (2009 ); Johnstone et al. (2010 ); Pertlik et al. (1990 ); Sasada et al. (1964 ). For uses of 2-alkoxybenzamides, see: van de Waterbeemd & Testa (1983 ); Kusunoki & Harada (1984 ). For the preparation of the title compound, see: Johnstone & Rose (1979 ).

Experimental

Crystal data

C₁₀H₁₃NO₂
M_r = 179.21
Monoclinic, P 2₁ /n
a = 6.0303 (4) Å
b = 11.1196 (8) Å
c = 14.4140 (11) Å
β = 98.647 (6)°
V = 955.54 (12) Å³
Z = 4
Cu Kα radiation
μ = 0.71 mm⁻¹
T = 100 K
0.16 × 0.10 × 0.08 mm

Data collection

Agilent SuperNova Atlas CCD diffractometer
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2012 ) T_min = 0.810, T_max = 1.000
2959 measured reflections
1676 independent reflections
1253 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.099
S = 1.03
1676 reflections
171 parameters
All H-atom parameters refined
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N13—H13A⋯O7	0.94 (2)	1.95 (2)	2.669 (2)	132.2 (15)
N13—H13B⋯O12ⁱ	0.93 (2)	1.98 (2)	2.911 (2)	173.5 (19)
C6—H6⋯O12ⁱⁱ	0.927 (19)	2.517 (18)	3.442 (2)	175.8 (14)
C5—H5⋯C11ⁱⁱⁱ	0.94 (2)	2.63 (2)	3.528 (2)	160.5 (17)
Symmetry codes: (i) -x, -y, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2012); 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) within OLEX2 (Dolomanov et al., 2009 ); molecular graphics: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812033326/gk2512sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812033326/gk2512Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812033326/gk2512Isup3.cml

checkCIF report

Comment top

In the 2-propoxybenzamide molecule, the C3—C2—C11—O12 torsion angle characterizing the twist of the benzene ring relative to the amide group is -11.5 (2)° and corresponding C6—C1—O7—C8 angle for the propoxy group is 3.0 (2)°. There is an intramolecular N13—H13A···O7 hydrogen bond within each molecule. The hydrogen bond N13—H13B···O12 (Table 1) plays a significant role in the packing of the title compound, forming pairs of inversion related molecules, with the molecular planes in parallel (Figure 2). These pairs form a nested network crystal, made of two layers, (-1 -2 2) and (-1 2 2), which form an angle of 84.40 (1)° between their planes (Figure 3). The molecules in layers are linked to each other by C6—H6···O12 interaction (Table 1). Within two parallel layers, pairs are lying with an offset to each other without any noticeable, direct interaction between them. The parallel layers are at a distance of 3.69 (2) Å from each other. They are further apart than is found for a similar packing of 2-hydroxybenzamide [2.91 (1) Å] (Johnstone et al., 2010). Along the a axis the pairs are ordered in two symmetry related columns. The plane of the benzene ring (C1—C6) of the 2-propoxybenzamide forms an angle of 34.43 (2)° with the column axis.

For 2-ethoxybenzamide, a homologue of the title compound, a similar formation of inversion related molecular pairs in the crystal was reported (Pagola & Stephens, 2009). The noticable difference in the packing of the two molecules stems from the larger dihedral angle between the carboxamide group and the benzene ring in 2-ethoxybenzamide of [50.48 (2)°] than found for 2-propoxybenzamide. Thus, 2-ethoxybenzamide does not exhibit an intramolecular hydrogen bond, which leads to a different intermolecular bonding network as compared to the title compound.

Related literature top

For crystal structures of similar compounds, see: Pagola & Stephens (2009); Johnstone et al. (2010); Pertlik et al. (1990); Sasada et al. (1964). For uses of 2-alkoxybenzamides, see: van de Waterbeemd & Testa (1983); Kusunoki & Harada (1984). For the preparation of the title compound, see: Johnstone & Rose (1979).

Experimental top

To powdered KOH (1.12 g, 20.0 mmol) in DMSO (9 ml) was added salicylamide (1.37 g, 10.0 mmol), and the resulting mixture was stirred for 10 min. at rt. Thereafter, n-propyl iodide (4.2 g, mmol, 24.7 mmol) was added dropwise. The solution was stirred for 12 h at rt. Then, it was poured into water (200 ml) and extracted with chloroform (3 x 50 ml). The organic phase was dried over anhydrous MgSO₄, concentrated in vacuo, and the residue was subjected to column chromatography on silica gel (CHCl₃/M^tBE 1:1) to give 2-propoxybenzamide (1.36 g, 77%) as colorless crystals (m.p. 375 K). The crystal was grown from chloroform/ M^tBE (v/v 1:1). IR (KBr) n_max 3445, 3325, 3273, 3180, 2964, 2935, 2877, 1665, 1594, 1454, 1378, 1277, 1237, 1042, 1010, 759, 566 cm^-1; ¹H NMR (DMSO-d⁶, 400 MHz) 0.97 (3H, t, ³J = 7.6 Hz), 1.76 (2H, qt, ³J = 7.6 Hz, ³J = 6.4 Hz), 4.04 (2H, t, ³J = 6.4 Hz), 6.99 (dd, ³J = 8.0 Hz, ³J = 8.0 Hz), 7.10 (1H, d, ³J = 8.0 Hz), 7.43 (1H, ddd, ³J = 8.0 Hz, ³J = 8.0 Hz, ⁴J = 2.0 Hz), 7.78 (1H, dd, ³J = 8.0 Hz, ⁴J = 2.0 Hz); ¹H NMR (CDCl₃, 400 MHz) 1.07 (3H, t, ³J = 7.4 Hz), 1.90 (2H, dd, ³J = 7.4 Hz, ³J = 6.5 Hz), 4.09 (2H, t, ³J = 6.5 Hz), 6.07 (1H, bs, NH), 6.96 (1H, d, ³J = 8.0 Hz), 7.05 (1H, dd, ³J = 7.8 Hz, ³J = 7.6 Hz), 7.44 (1H, dd, ³J = 8.0 Hz, ³J = 7.6 Hz, ⁴J = 1.8 Hz), 7.84 (1H, bs, NH), 8.20 (1H, dd, ³J = 7.8 Hz, ⁴J = 1.8 Hz); ¹³C NMR (DMSO-d⁶, 400 MHz) 11.0, 22.3, 70.4, 113.3, 120.8, 123.1, 131.2, 132.9, 157.0, 166.8; ¹³C NMR (CDCl₃, 400 MHz) 10.7, 22.6, 71.0, 112.8, 121.4, 121.7, 133.2, 134.0, 158.2, 168.1.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within OLEX2 (Dolomanov et al., 2009); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the title compound molecule with the atom-numbering scheme and the intramolecular interaction within the molecule. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. Intermolecular and intramolecular attractions between molecules of the title compound. [Symmetry codes: (i): -x,1 - y,1 - z (ii): 1/2 - x,1/2 + y,1.5 - z (iii): 1/2 + x,1/2 - y,1/2 + z (iiii): 1 + x,y,z]
	Fig. 3. The crystal network formed by the layers of molecular pairs in the planes (-1 2 2) in blue, and (-1 –2 2) in green.

2-propoxybenzamide top

Crystal data top

C₁₀H₁₃NO₂	D_x = 1.246 Mg m⁻³
M_r = 179.21	Melting point: 375 K
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.5418 Å
a = 6.0303 (4) Å	Cell parameters from 1037 reflections
b = 11.1196 (8) Å	θ = 3.1–66.6°
c = 14.4140 (11) Å	µ = 0.71 mm⁻¹
β = 98.647 (6)°	T = 100 K
V = 955.54 (12) Å³	Block, colourless
Z = 4	0.16 × 0.10 × 0.08 mm
F(000) = 384

Data collection top

Agilent SuperNova Atlas CCD diffractometer	1676 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1253 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.035
Detector resolution: 10.4948 pixels mm^-1	θ_max = 66.7°, θ_min = 5.1°
ω scans	h = −7→7
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2012)	k = −13→13
T_min = 0.810, T_max = 1.000	l = −17→15
2959 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)] = 0.040	All H-atom parameters refined
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0471P)²P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
1676 reflections	Δρ_max = 0.21 e Å⁻³
171 parameters	Δρ_min = −0.17 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: 0.0017 (4)

Crystal data top

C₁₀H₁₃NO₂	V = 955.54 (12) Å³
M_r = 179.21	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 6.0303 (4) Å	µ = 0.71 mm⁻¹
b = 11.1196 (8) Å	T = 100 K
c = 14.4140 (11) Å	0.16 × 0.10 × 0.08 mm
β = 98.647 (6)°

Data collection top

Agilent SuperNova Atlas CCD diffractometer	1676 independent reflections
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2012)	1253 reflections with I > 2σ(I)
T_min = 0.810, T_max = 1.000	R_int = 0.035
2959 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.099	All H-atom parameters refined
S = 1.03	Δρ_max = 0.21 e Å⁻³
1676 reflections	Δρ_min = −0.17 e Å⁻³
171 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
C1	0.0319 (3)	0.24260 (15)	0.75450 (12)	0.0205 (4)
C10	0.7095 (3)	0.1142 (2)	0.96172 (14)	0.0319 (5)
C11	−0.0529 (3)	0.13553 (15)	0.59371 (12)	0.0210 (4)
C2	−0.1026 (3)	0.22312 (15)	0.66721 (12)	0.0206 (4)
C3	−0.3032 (3)	0.28748 (16)	0.64722 (13)	0.0246 (4)
C4	−0.3695 (3)	0.36968 (16)	0.70979 (13)	0.0274 (4)
C5	−0.2326 (3)	0.38823 (16)	0.79474 (13)	0.0263 (4)
C6	−0.0335 (3)	0.32574 (16)	0.81744 (13)	0.0240 (4)
C8	0.3557 (3)	0.18715 (17)	0.86630 (12)	0.0240 (4)
C9	0.5534 (3)	0.10404 (17)	0.86848 (13)	0.0245 (4)
H10A	0.766 (3)	0.198 (2)	0.9734 (15)	0.049 (7)*
H10B	0.839 (4)	0.054 (2)	0.9640 (14)	0.047 (6)*
H10C	0.634 (4)	0.092 (2)	1.0150 (17)	0.051 (7)*
H13A	0.256 (3)	0.1050 (18)	0.6538 (15)	0.035 (6)*
H13B	0.175 (3)	0.028 (2)	0.5573 (15)	0.043 (6)*
H3	−0.394 (3)	0.2739 (16)	0.5883 (13)	0.022 (5)*
H4	−0.515 (3)	0.4133 (18)	0.6958 (14)	0.040 (6)*
H5	−0.273 (3)	0.4440 (19)	0.8381 (15)	0.038 (6)*
H6	0.056 (3)	0.3387 (15)	0.8747 (13)	0.020 (5)*
H8A	0.408 (3)	0.2707 (16)	0.8776 (13)	0.019 (4)*
H8B	0.263 (3)	0.1645 (17)	0.9168 (15)	0.034 (5)*
H9A	0.499 (3)	0.0208 (18)	0.8581 (13)	0.031 (5)*
H9B	0.635 (3)	0.1262 (16)	0.8153 (14)	0.027 (5)*
N13	0.1514 (3)	0.08719 (15)	0.60043 (11)	0.0273 (4)
O12	−0.2027 (2)	0.10985 (11)	0.52757 (8)	0.0268 (3)
O7	0.22330 (19)	0.17526 (11)	0.77463 (8)	0.0236 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0192 (8)	0.0205 (9)	0.0215 (9)	−0.0012 (7)	0.0020 (7)	0.0020 (7)
C10	0.0287 (11)	0.0383 (12)	0.0259 (11)	0.0009 (10)	−0.0053 (8)	0.0023 (9)
C11	0.0259 (9)	0.0184 (9)	0.0181 (9)	−0.0040 (7)	0.0012 (7)	0.0020 (7)
C2	0.0230 (9)	0.0191 (9)	0.0197 (9)	−0.0042 (7)	0.0031 (7)	0.0015 (7)
C3	0.0250 (9)	0.0242 (10)	0.0232 (10)	−0.0015 (8)	−0.0014 (8)	0.0037 (7)
C4	0.0259 (10)	0.0260 (10)	0.0305 (11)	0.0034 (8)	0.0048 (8)	0.0037 (8)
C5	0.0302 (11)	0.0218 (10)	0.0272 (10)	0.0009 (8)	0.0057 (8)	−0.0030 (8)
C6	0.0279 (10)	0.0231 (9)	0.0207 (10)	−0.0030 (8)	0.0024 (8)	−0.0034 (8)
C8	0.0233 (10)	0.0301 (11)	0.0171 (9)	−0.0007 (8)	−0.0021 (7)	−0.0034 (8)
C9	0.0247 (10)	0.0268 (10)	0.0210 (10)	0.0005 (8)	0.0003 (7)	−0.0008 (8)
N13	0.0271 (9)	0.0319 (9)	0.0220 (9)	0.0020 (7)	0.0004 (7)	−0.0081 (7)
O12	0.0314 (7)	0.0257 (7)	0.0207 (7)	−0.0001 (6)	−0.0044 (5)	−0.0015 (5)
O7	0.0219 (6)	0.0295 (7)	0.0177 (7)	0.0040 (5)	−0.0025 (5)	−0.0043 (5)

Geometric parameters (Å, º) top

C1—C2	1.407 (2)	C6—H6	0.927 (19)
C1—C6	1.393 (2)	C8—C9	1.505 (3)
C10—H10A	1.00 (2)	C8—H8A	0.987 (18)
C10—H10B	1.03 (2)	C8—H8B	1.01 (2)
C10—H10C	0.98 (2)	C9—C10	1.525 (3)
C2—C11	1.502 (2)	C9—H9A	0.99 (2)
C2—C3	1.398 (2)	N13—C11	1.334 (2)
C3—C4	1.385 (3)	N13—H13A	0.94 (2)
C3—H3	0.951 (18)	N13—H13B	0.93 (2)
C4—H4	0.996 (19)	O12—C11	1.244 (2)
C5—C4	1.386 (3)	O7—C1	1.370 (2)
C5—H5	0.94 (2)	O7—C8	1.444 (2)
C6—C5	1.383 (3)

C1—C6—H6	119.9 (11)	C8—C9—H9A	109.2 (11)
C1—C2—C11	125.52 (15)	C8—C9—C10	110.78 (16)
C1—O7—C8	118.44 (13)	C9—C10—H10C	111.9 (14)
C10—C9—H9B	110.3 (11)	C9—C10—H10B	110.3 (12)
C10—C9—H9A	110.5 (11)	C9—C10—H10A	111.6 (12)
C11—N13—H13B	117.9 (12)	C9—C8—H8B	110.7 (11)
C11—N13—H13A	118.3 (12)	C9—C8—H8A	110.0 (11)
C2—C3—H3	117.9 (11)	H10A—C10—H10C	106.8 (18)
C3—C4—H4	121.4 (12)	H10A—C10—H10B	111.4 (17)
C3—C4—C5	118.80 (17)	H10B—C10—H10C	104.6 (18)
C3—C2—C11	116.41 (15)	H13A—N13—H13B	123.0 (17)
C3—C2—C1	118.04 (16)	H8A—C8—H8B	108.2 (15)
C4—C5—H5	120.5 (12)	H9A—C9—H9B	107.8 (15)
C4—C3—H3	120.2 (11)	N13—C11—C2	119.34 (15)
C4—C3—C2	121.97 (17)	O12—C11—C2	119.37 (15)
C5—C6—H6	120.1 (11)	O12—C11—N13	121.30 (17)
C5—C4—H4	119.7 (12)	O7—C8—H8B	110.2 (11)
C5—C6—C1	120.01 (17)	O7—C8—H8A	110.9 (11)
C6—C5—H5	118.5 (12)	O7—C8—C9	106.87 (14)
C6—C5—C4	121.00 (18)	O7—C1—C6	122.48 (16)
C6—C1—C2	120.17 (16)	O7—C1—C2	117.33 (15)
C8—C9—H9B	108.2 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13A···O7	0.94 (2)	1.95 (2)	2.669 (2)	132.2 (15)
N13—H13B···O12ⁱ	0.93 (2)	1.98 (2)	2.911 (2)	173.5 (19)
C6—H6···O12ⁱⁱ	0.927 (19)	2.517 (18)	3.442 (2)	175.8 (14)
C5—H5···C11ⁱⁱⁱ	0.94 (2)	2.63 (2)	3.528 (2)	160.5 (17)

Symmetry codes: (i) −x, −y, −z+1; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x−1/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO₂
M_r	179.21
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	6.0303 (4), 11.1196 (8), 14.4140 (11)
β (°)	98.647 (6)
V (Å³)	955.54 (12)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.16 × 0.10 × 0.08

Data collection
Diffractometer	Agilent SuperNova Atlas CCD diffractometer
Absorption correction	Gaussian (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.810, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	2959, 1676, 1253
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.099, 1.03
No. of reflections	1676
No. of parameters	171
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.17

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) within OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N13—H13A···O7	0.94 (2)	1.95 (2)	2.669 (2)	132.2 (15)
N13—H13B···O12ⁱ	0.93 (2)	1.98 (2)	2.911 (2)	173.5 (19)
C6—H6···O12ⁱⁱ	0.927 (19)	2.517 (18)	3.442 (2)	175.8 (14)
C5—H5···C11ⁱⁱⁱ	0.94 (2)	2.63 (2)	3.528 (2)	160.5 (17)

Symmetry codes: (i) −x, −y, −z+1; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x−1/2, y+1/2, −z+3/2.

Acknowledgements

We thank Miss M. al Hindawi for spectroscopic measurements of the title compound.

References

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