N-[3,5-Bis­(tri­fluoro­methyl)­phenyl]­salicyl­ald­imine

Karadayı, N.; Gözüyeşil, S.; Güzel, B.; Büyükgüngör, O.

doi:10.1107/S1600536803000722

N-[3,5-Bis(trifluoromethyl)phenyl]salicylaldimine

N. Karadayı, S. Gözüyeşil, B. Güzel and O. Büyükgüngör

The title compound, C₁₅H₉F₆NO, is non-planar with a dihedral angle between the two aromatic rings of 29.57 (2)°. The central N=C bond distance of 1.276 (4) Å is typical for a double bond. There are intramolecular O—H

N and weak intermolecular C—H

F hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803000722/ob6204sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803000722/ob6204Isup2.hkl Contains datablock I

CCDC reference: 204690

checkCIF report

Key indicators

Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.005 Å
R factor = 0.063
wR factor = 0.191
Data-to-parameter ratio = 9.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



SHFSU_01  Alert C The absolute value of parameter shift to su ratio > 0.05
          Absolute value of the parameter shift to su ratio given   0.062
          Additional refinement cycles may be required.

PLAT_213  Alert C Atom F4B     has ADP max/min Ratio ...........       3.20 prolate


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

Comment top

Solvent extraction is now widely accepted as a process for the recovery of metal ions from aqueus solution in hydrometallurgical and environmental application (El Aamrani et al., 1999) with new interest in the processing of heavy metals by chelation incorporated with supercritical fluid (SCF) extraction processing. We have designed novel Shiff base type chelating agents by attaching CO₂-philic fluoroalkyl groups, and synthesized and characterized these compounds for supercritical CO₂ extraction of heavy metals. In this study, we report the structure of the title compound, (I).

The molecule structure of (I) is shown in Fig. 1. The C8—N1 and C7—C6 bond lengths are 1.417 (4) and 1.439 (4) Å, respectively (Table 1), and agree with the corresponding distances in 2-[(4-hydroxyphenyl)iminomethyl]thiophene [1.422 (2) and 1.447 (3) Å; Kazak et al., 2000] and trans-[4-dimethylaminophenyl)iminomethyl]-N-methylpyridinium para-toluenesulfonate [1.413 (3) and 1.461 Å; Coe et al., 2001]. The N1═C7 bond length of 1.276 (4) Å is typical of a double bond, which is similar to the corresponding bond lenghts in N-(2,4-dinitrophenyl)-N-methylhydrazone [1.279 (2) Å; Aygün et al., 1998], 2-salicylideneamino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrite [1.281 (2) Å; Elerman & Elmalı, 1998] and 2-[(4-hydroxyphenyl)iminomethyl]thiophene [1.282 (2) Å; Kazak et al., 2000]. The O1—C5 distance of 1.360 (4) Å is nearly equal to the value of 1.349 (6) Å in 3-tert-butyl-2-hydroxy-5-methoxyazobenzene (Işık et al., 1998). The two aromatic rings have different orientations and the dihedral angle between the rings formed by atoms C1–C6 and C8–C13 is 29.57 (2)°.

There is an intramolecular O1—H1···N1 hydrogen bond and an intermolecular C7—H7···F1A hydrogen bond (Table 2). Both CF₃ groups showed rotational disorder.

Experimental top

An ethanol solution of 3,5-bis(trifluoromethyl)aminobenzene (2.29 g/20 ml e thanol) was added dropwise at room temperature to a solution of salicylaldehyde (1.22 g, 0.01 mol) in ethanol (20 ml) and large amounts of a yellow precipitate were formed. The mixture was stirred for 30 min at this temperature and filtered under vacuum. Spectroscopically pure (I) was obtained by crystallization from toluene as pale-yellow needles (yield: 93%, m.p.: 369–371 K); elemental analysis, calculated for C₁₅H₉F₆N: C 54.05, H 2.70, N 4.20%; found: C 54.34, H 2.78, N 4.19%. ¹H NMR (CDCl₃, 400 MHz): δ 6.9–7.1 (m, 7H, Ar—H), 8.5 (s, 1H, H—C═N), 12.2 (s, 1H, OH). IR (KBr) 3600–3300 (br, Ph—OH), 2950 (H—CN), 1650 (C═N), 1600 (Ar—CH). Uv–vis (CHCl₃): λ = 240 (ε: 2000), 276 (max., ε: 2927), 346 nm (ε: 1835).

Computing details top

Data collection: XSCANS (Siemens, 1991); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and PLATON (Spek, 1997).

Figures top

	Fig. 1. An ORTEPIII (Burnett & Johnson, 1996) drawing of (I), showing the atomic numbering scheme. Displacement ellipsoids for non-H atoms are shown at the 30% probability level. The site-occupancy factors are 0.64 (1) and 0.36 (1) for F1A–F6A and F1B–F6B, respectively.
	Fig. 2. PLATON/PLUTON plot (Spek, 1997), showing part of the hydrogen-bond network and the stacking of molecules. The disordered F atoms with 36% occupancy have been omitted for clarity.

N-[3,5-bis(trifluoromethyl)benzene]-salicylaldimine top

Crystal data top

C₁₅H₉F₆NO	F(000) = 672
M_r = 333.23	D_x = 1.586 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 35 reflections
a = 7.509 (1) Å	θ = 5–25°
b = 26.634 (2) Å	µ = 0.16 mm⁻¹
c = 7.854 (1) Å	T = 180 K
β = 117.34 (1)°	Plate, yellow
V = 1395.3 (3) Å³	0.3 × 0.3 × 0.02 mm
Z = 4

Data collection top

Siemens P4 diffractometer	R_int = 0.068
Radiation source: fine-focus sealed tube	θ_max = 25.2°, θ_min = 3.4°
Graphite monochromator	h = −4→9
ω scans	k = −30→31
9212 measured reflections	l = −9→9
2508 independent reflections	1 standard reflections every 120 min
1400 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.063	H-atom parameters constrained
wR(F²) = 0.191	w = 1/[σ²(F_o²) + (0.0908P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.062
2508 reflections	Δρ_max = 0.22 e Å⁻³
264 parameters	Δρ_min = −0.23 e Å⁻³
346 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (3)

Crystal data top

C₁₅H₉F₆NO	V = 1395.3 (3) Å³
M_r = 333.23	Z = 4
Monoclinic, P2₁/a	Mo Kα radiation
a = 7.509 (1) Å	µ = 0.16 mm⁻¹
b = 26.634 (2) Å	T = 180 K
c = 7.854 (1) Å	0.3 × 0.3 × 0.02 mm
β = 117.34 (1)°

Data collection top

Siemens P4 diffractometer	R_int = 0.068
9212 measured reflections	1 standard reflections every 120 min
2508 independent reflections	intensity decay: none
1400 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.063	346 restraints
wR(F²) = 0.191	H-atom parameters constrained
S = 1.06	Δρ_max = 0.22 e Å⁻³
2508 reflections	Δρ_min = −0.23 e Å⁻³
264 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. The structure was solved by direct methods and refined using full-matrix least squares with all non-H atoms anisotropic. 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)
C12	0.2074 (4)	0.90153 (12)	0.1261 (5)	0.0490 (8)
C14	−0.0075 (6)	0.91051 (14)	−0.0061 (6)	0.0642 (10)
F1A	−0.1096 (9)	0.8692 (2)	−0.0784 (14)	0.116 (4)	0.639 (14)
F2A	−0.0984 (9)	0.9350 (5)	0.0669 (11)	0.138 (5)	0.639 (14)
F3A	−0.0283 (8)	0.9355 (4)	−0.1585 (10)	0.132 (4)	0.639 (14)
F1B	−0.0707 (16)	0.8904 (7)	−0.1714 (14)	0.109 (6)	0.361 (14)
F2B	−0.1287 (11)	0.8926 (6)	0.0629 (18)	0.102 (5)	0.361 (14)
F3B	−0.0635 (14)	0.9572 (3)	−0.035 (3)	0.103 (6)	0.361 (14)
C10	0.5439 (5)	0.93086 (12)	0.2953 (5)	0.0501 (9)
C15	0.6928 (5)	0.97260 (14)	0.3501 (6)	0.0623 (10)
F4A	0.8756 (8)	0.9567 (3)	0.4029 (13)	0.096 (2)	0.639 (14)
F5A	0.7045 (13)	0.9985 (4)	0.4971 (9)	0.089 (2)	0.639 (14)
F6A	0.6681 (17)	1.0013 (5)	0.2131 (15)	0.144 (5)	0.639 (14)
F4B	0.8762 (16)	0.9587 (6)	0.451 (3)	0.149 (7)	0.361 (14)
F5B	0.637 (4)	1.0118 (7)	0.410 (4)	0.166 (7)	0.361 (14)
F6B	0.6673 (18)	0.9991 (7)	0.193 (2)	0.087 (5)	0.361 (14)
O1	0.4776 (3)	0.69821 (9)	0.3629 (4)	0.0642 (7)
H1	0.4496	0.7277	0.3320	0.096*
N1	0.5228 (4)	0.79528 (10)	0.3935 (4)	0.0493 (7)
C1	0.9071 (5)	0.73333 (14)	0.8136 (5)	0.0562 (9)
H1A	0.9718	0.7618	0.8826	0.067*
C2	0.9792 (6)	0.68696 (15)	0.8896 (6)	0.0657 (11)
H2	1.0923	0.6840	1.0078	0.079*
C3	0.8803 (6)	0.64458 (16)	0.7871 (6)	0.0678 (11)
H3	0.9279	0.6129	0.8377	0.081*
C4	0.7136 (5)	0.64847 (14)	0.6129 (6)	0.0635 (10)
H4	0.6480	0.6197	0.5464	0.076*
C5	0.6433 (5)	0.69580 (13)	0.5362 (5)	0.0527 (9)
C6	0.7410 (5)	0.73888 (12)	0.6373 (5)	0.0481 (8)
C7	0.6716 (5)	0.78797 (13)	0.5579 (5)	0.0503 (9)
H7	0.7386	0.8158	0.6303	0.060*
C8	0.4697 (5)	0.84496 (12)	0.3242 (4)	0.0462 (8)
C9	0.6062 (4)	0.88344 (12)	0.3683 (5)	0.0497 (9)
H9	0.7414	0.8774	0.4480	0.060*
C11	0.3427 (5)	0.94034 (13)	0.1737 (5)	0.0531 (9)
H11	0.3003	0.9724	0.1253	0.064*
C13	0.2691 (4)	0.85405 (13)	0.1997 (5)	0.0494 (9)
H13	0.1763	0.8281	0.1660	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C12	0.0446 (18)	0.053 (2)	0.0483 (19)	−0.0005 (16)	0.0202 (16)	−0.0031 (16)
C14	0.058 (2)	0.059 (2)	0.065 (2)	−0.0027 (19)	0.019 (2)	−0.004 (2)
F1A	0.060 (3)	0.080 (4)	0.140 (8)	−0.013 (2)	−0.013 (4)	−0.025 (4)
F2A	0.071 (4)	0.206 (12)	0.119 (6)	0.044 (7)	0.027 (3)	−0.061 (7)
F3A	0.070 (3)	0.193 (10)	0.099 (5)	0.003 (4)	0.010 (3)	0.067 (6)
F1B	0.081 (7)	0.134 (14)	0.072 (6)	0.012 (8)	0.002 (5)	−0.041 (7)
F2B	0.046 (4)	0.122 (11)	0.125 (9)	−0.004 (6)	0.029 (5)	0.025 (8)
F3B	0.062 (5)	0.057 (5)	0.158 (14)	0.021 (3)	0.023 (7)	0.003 (5)
C10	0.0493 (19)	0.050 (2)	0.0485 (19)	−0.0072 (16)	0.0201 (16)	−0.0030 (16)
C15	0.065 (2)	0.048 (2)	0.068 (2)	−0.0061 (18)	0.025 (2)	0.0044 (19)
F4A	0.059 (3)	0.077 (4)	0.174 (6)	−0.024 (3)	0.073 (4)	−0.038 (4)
F5A	0.090 (4)	0.090 (5)	0.097 (4)	−0.046 (3)	0.053 (3)	−0.053 (3)
F6A	0.172 (8)	0.115 (8)	0.094 (5)	−0.089 (5)	0.017 (5)	0.016 (5)
F4B	0.086 (7)	0.090 (9)	0.145 (9)	−0.040 (5)	−0.055 (7)	0.071 (7)
F5B	0.211 (17)	0.107 (11)	0.278 (19)	−0.093 (9)	0.197 (16)	−0.109 (14)
F6B	0.055 (6)	0.107 (12)	0.097 (9)	−0.003 (7)	0.032 (6)	0.048 (8)
O1	0.0539 (15)	0.0540 (15)	0.0853 (18)	−0.0043 (11)	0.0326 (14)	−0.0109 (13)
N1	0.0473 (16)	0.0478 (17)	0.0591 (18)	0.0004 (12)	0.0300 (15)	0.0010 (14)
C1	0.058 (2)	0.062 (2)	0.054 (2)	0.0021 (17)	0.0300 (18)	0.0056 (18)
C2	0.065 (2)	0.077 (3)	0.065 (2)	0.007 (2)	0.038 (2)	0.016 (2)
C3	0.071 (2)	0.063 (3)	0.086 (3)	0.015 (2)	0.050 (2)	0.023 (2)
C4	0.064 (2)	0.049 (2)	0.092 (3)	−0.0026 (18)	0.048 (2)	0.006 (2)
C5	0.0420 (18)	0.056 (2)	0.068 (2)	−0.0014 (16)	0.0323 (19)	0.0015 (19)
C6	0.0514 (19)	0.045 (2)	0.060 (2)	0.0015 (15)	0.0361 (17)	0.0002 (16)
C7	0.0496 (19)	0.054 (2)	0.056 (2)	−0.0053 (16)	0.0317 (18)	−0.0051 (17)
C8	0.0470 (18)	0.0478 (19)	0.0478 (18)	−0.0036 (15)	0.0250 (16)	−0.0054 (15)
C9	0.0403 (17)	0.055 (2)	0.0520 (19)	−0.0026 (15)	0.0199 (15)	−0.0017 (17)
C11	0.060 (2)	0.048 (2)	0.0524 (19)	0.0018 (16)	0.0267 (18)	0.0000 (16)
C13	0.0465 (19)	0.050 (2)	0.0543 (19)	−0.0090 (15)	0.0249 (17)	−0.0093 (17)

Geometric parameters (Å, º) top

C12—C11	1.375 (4)	N1—C7	1.276 (4)
C12—C13	1.379 (5)	N1—C8	1.417 (4)
C12—C14	1.483 (5)	C1—C2	1.370 (5)
C14—F2A	1.257 (6)	C1—C6	1.381 (4)
C14—F1B	1.277 (8)	C1—H1A	0.9300
C14—F3B	1.299 (7)	C2—C3	1.387 (5)
C14—F1A	1.312 (6)	C2—H2	0.9300
C14—F3A	1.315 (6)	C3—C4	1.370 (5)
C14—F2B	1.343 (8)	C3—H3	0.9300
C10—C9	1.377 (4)	C4—C5	1.392 (5)
C10—C11	1.391 (4)	C4—H4	0.9300
C10—C15	1.493 (5)	C5—C6	1.397 (5)
C15—F6A	1.262 (8)	C6—C7	1.439 (4)
C15—F4B	1.289 (10)	C7—H7	0.9300
C15—F5B	1.294 (11)	C8—C9	1.377 (4)
C15—F4A	1.309 (6)	C8—C13	1.389 (4)
C15—F5A	1.313 (7)	C9—H9	0.9300
C15—F6B	1.355 (10)	C11—H11	0.9300
O1—C5	1.360 (4)	C13—H13	0.9300
O1—H1	0.8200

C11—C12—C13	120.7 (3)	C2—C1—H1A	119.1
C11—C12—C14	120.0 (3)	C6—C1—H1A	119.1
C13—C12—C14	119.3 (3)	C1—C2—C3	118.8 (4)
F1B—C14—F3B	106.5 (9)	C1—C2—H2	120.6
F2A—C14—F1A	107.5 (6)	C3—C2—H2	120.6
F2A—C14—F3A	106.8 (7)	C4—C3—C2	121.2 (4)
F1A—C14—F3A	103.3 (6)	C4—C3—H3	119.4
F1B—C14—F2B	104.9 (9)	C2—C3—H3	119.4
F3B—C14—F2B	100.7 (8)	C3—C4—C5	119.5 (4)
F2A—C14—C12	114.1 (4)	C3—C4—H4	120.3
F1B—C14—C12	114.9 (6)	C5—C4—H4	120.3
F3B—C14—C12	115.9 (5)	O1—C5—C4	117.8 (3)
F1A—C14—C12	113.6 (4)	O1—C5—C6	122.0 (3)
F3A—C14—C12	110.8 (4)	C4—C5—C6	120.1 (3)
F2B—C14—C12	112.4 (5)	C1—C6—C5	118.6 (3)
C9—C10—C11	120.5 (3)	C1—C6—C7	120.8 (3)
C9—C10—C15	119.8 (3)	C5—C6—C7	120.6 (3)
C11—C10—C15	119.7 (3)	N1—C7—C6	123.5 (3)
F4B—C15—F5B	116.3 (13)	N1—C7—H7	118.3
F6A—C15—F4A	100.8 (8)	C6—C7—H7	118.3
F6A—C15—F5A	110.8 (8)	C9—C8—C13	119.3 (3)
F4A—C15—F5A	104.7 (5)	C9—C8—N1	123.6 (3)
F4B—C15—F6B	112.0 (10)	C13—C8—N1	117.1 (3)
F5B—C15—F6B	88.8 (15)	C8—C9—C10	120.4 (3)
F6A—C15—C10	114.0 (6)	C8—C9—H9	119.8
F4B—C15—C10	114.2 (7)	C10—C9—H9	119.8
F5B—C15—C10	112.3 (10)	C12—C11—C10	119.0 (3)
F4A—C15—C10	112.9 (4)	C12—C11—H11	120.5
F5A—C15—C10	112.6 (6)	C10—C11—H11	120.5
F6B—C15—C10	110.5 (8)	C12—C13—C8	120.1 (3)
C5—O1—H1	109.5	C12—C13—H13	119.9
C7—N1—C8	119.5 (3)	C8—C13—H13	119.9
C2—C1—C6	121.8 (4)

C11—C12—C14—F2A	−73.1 (9)	C2—C3—C4—C5	0.7 (5)
C13—C12—C14—F2A	107.0 (8)	C3—C4—C5—O1	179.9 (3)
C11—C12—C14—F1B	109.6 (11)	C3—C4—C5—C6	−0.6 (5)
C13—C12—C14—F1B	−70.2 (11)	C2—C1—C6—C5	0.9 (5)
C11—C12—C14—F3B	−15.4 (12)	C2—C1—C6—C7	−178.2 (3)
C13—C12—C14—F3B	164.7 (11)	O1—C5—C6—C1	179.3 (3)
C11—C12—C14—F1A	163.2 (7)	C4—C5—C6—C1	−0.1 (5)
C13—C12—C14—F1A	−16.7 (8)	O1—C5—C6—C7	−1.6 (5)
C11—C12—C14—F3A	47.5 (8)	C4—C5—C6—C7	179.0 (3)
C13—C12—C14—F3A	−132.3 (7)	C8—N1—C7—C6	−177.7 (3)
C11—C12—C14—F2B	−130.5 (9)	C1—C6—C7—N1	177.8 (3)
C13—C12—C14—F2B	49.6 (9)	C5—C6—C7—N1	−1.3 (5)
C9—C10—C15—F6A	138.9 (9)	C7—N1—C8—C9	31.6 (5)
C11—C10—C15—F6A	−42.4 (9)	C7—N1—C8—C13	−150.8 (3)
C9—C10—C15—F4B	6.3 (12)	C13—C8—C9—C10	2.2 (5)
C11—C10—C15—F4B	−174.9 (11)	N1—C8—C9—C10	179.8 (3)
C9—C10—C15—F5B	−128.9 (15)	C11—C10—C9—C8	−0.9 (5)
C11—C10—C15—F5B	49.9 (16)	C15—C10—C9—C8	177.8 (3)
C9—C10—C15—F4A	24.6 (6)	C13—C12—C11—C10	1.0 (5)
C11—C10—C15—F4A	−156.6 (5)	C14—C12—C11—C10	−178.9 (3)
C9—C10—C15—F5A	−93.7 (6)	C9—C10—C11—C12	−0.6 (5)
C11—C10—C15—F5A	85.0 (6)	C15—C10—C11—C12	−179.4 (3)
C9—C10—C15—F6B	133.7 (8)	C11—C12—C13—C8	0.3 (5)
C11—C10—C15—F6B	−47.6 (8)	C14—C12—C13—C8	−179.8 (3)
C6—C1—C2—C3	−0.9 (5)	C9—C8—C13—C12	−1.9 (5)
C1—C2—C3—C4	0.1 (5)	N1—C8—C13—C12	−179.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.88	2.604 (4)	147
C7—H7···F1Aⁱ	0.93	2.48	3.351 (8)	156

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

Experimental details

Crystal data
Chemical formula	C₁₅H₉F₆NO
M_r	333.23
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	180
a, b, c (Å)	7.509 (1), 26.634 (2), 7.854 (1)
β (°)	117.34 (1)
V (Å³)	1395.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.3 × 0.3 × 0.02

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9212, 2508, 1400
R_int	0.068
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.191, 1.06
No. of reflections	2508
No. of parameters	264
No. of restraints	346
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.23

Computer programs: XSCANS (Siemens, 1991), XSCANS, SHELXTL (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and PLATON (Spek, 1997).

Selected geometric parameters (Å, º) top

C12—C11	1.375 (4)	N1—C8	1.417 (4)
C12—C13	1.379 (5)	C1—C6	1.381 (4)
O1—C5	1.360 (4)	C6—C7	1.439 (4)
N1—C7	1.276 (4)	C8—C9	1.377 (4)

C11—C12—C13	120.7 (3)	C1—C6—C7	120.8 (3)
C11—C12—C14	120.0 (3)	C5—C6—C7	120.6 (3)
C13—C12—C14	119.3 (3)	N1—C7—C6	123.5 (3)
C7—N1—C8	119.5 (3)	C9—C8—N1	123.6 (3)
O1—C5—C4	117.8 (3)	C13—C8—N1	117.1 (3)