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

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

doi:10.1107/S1600536803010730

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

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

In the title compound, C₁₆H₁₁NO₂F₆, the two aromatic rings are somewhat twisted with respect to each other, forming a dihedral angle of 35.12 (4)°. The N=C bond distance of 1.287 (5) Å is typical for a double bond. In the crystal structure, the molecules are linked by intramolecular O—H

N and intermolecular C—H

F hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803010730/wn6153sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803010730/wn6153Isup2.hkl Contains datablock I

CCDC reference: 214845

checkCIF report

Key indicators

Single-crystal X-ray study
T = 180 K
Mean (C-C) = 0.005 Å
R factor = 0.069
wR factor = 0.195
Data-to-parameter ratio = 10.2

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   0.060
          Additional refinement cycles may be required.

PLAT_213  Alert C Atom F6B     has ADP max/min Ratio ...........       3.10 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 aqueous solution in hydrometallurgical and environmental applications (El Aamrani et al., 1999), with new interest in the processing of heavy metals by chelation in combination with supercritical fluid (SCF) extraction processing. Carbon dioxide is commonly employed in SCF processing because it is readly available, inexpensive, non-toxic and non-flammable (Yazdı et al., 1996; Cross et al., 1996). Solubilities of known ligands in sc CO₂ are generally low compared to solubilities in organic solvents. Data indicate that fluorination of chelating agents results in dramatic enhancement of solubility. In this work, we have designed a novel Schiff base type chelating agent, by attaching a CO₂-philic fluoroalkyl group; this has been synthesized, and characterized for sc CO₂ extraction of heavy metals.

Most aromatic compounds which contain a trifluoromethyl group are known to have higher melting points, in some cases significantly higher, than the corresponding methyl-substituted compounds. The latter, however, despite their lower molecular weight, generally have higher boiling points. Apparently, forces exist in the crystalline state between molecules containing a CF₃ group which are stronger than in the corresponding methyl-substituted compounds, but which are absent in the liquid state (Boitsov et al., 2002).

The molecular structure of (I) is shown in Fig. 1. The C9—N1 and C7—C6 bond lengths are 1.412 (4) and 1.442 (4) Å; these are in agreement with the corresponding distances in trans-4-[(4-dimethylaminophenyl)iminomethyl]-N-methylpyridinium p-toluenesulfonate [1.413 (3) and 1.461 (3) Å; Coe et al., 2001] and N-[3,5-bis(trifluoromethyl)phenyl]salicylaldimine [1.417 (4) and 1.439 (4) Å; Karadayı et al., 2003]. The O1—C5, O2—C4 and O2—C8 bond lengths are 1.352 (3), 1.361 (4) and 1.430 (4) Å, respectively, and agree with the corresponding distances in (E)-2-hydroxy-3,3',4'-trimethoxystilbene [1.369 (2), 1.371 (2) and 1.427 (3) Å; Stomberg et al., 1998]. The N1═C7 bond length is 1.287 (5) Å, approximately equal to previously reported C═N double-bond lengths (Elerman & Elmalı, 1998; Karadayı et al., 2003; Kazak et al., 2000).

One intramolecular O—H···N hydrogen bond and one intermolecular C—H···F hydrogen bond are present in the crystal structure (Table 2).

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 3-methoxysalicylaldehyde (o-vanillin) (1.52 g, 0.01 mol) in ethanol (20 ml), yielding large amounts of a pale yellow precipitate. The mixture was stirred for 30 min at this temperature and filtered under vacuum. Crystallization from toluene gave a spectroscopically pure product as a pale yellow plate-like crystalline compound (yield: 91%, m.p.: 394–396 K); elemental analysis calculated for C₁₆H₁₁F₆N: C 52.89, H 3.03, N 3.85%; found: C 52.82, H 2.89, N 3.83%; ¹H NMR (CDCl₃, 400 MHz): δ = 3.8 (s, 3H, O—CH₃), 6.6–7.4 (m, 6H, Ar—H), 8.4 (s, 1H, H—C═N), 12.4 (s, 1H, OH). IR (KBr): 3600–3300 (br, Ph—OH), 2950 (H—CN), 1650 (C═N), 1600 (Ar—CH). UV-vis (CHCl₃): λ = 245 (ε: 2125), 305 (max., ε: 3163), 368 nm (ε: 1088).

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 the title compound, (I), showing the atomic numbering scheme. Displacement ellipsoids of non-H atoms are drawn at the 30% probability level.
	Fig. 2. PLATON plot (Spek, 1997), viewed down the c axis, showing part of the hydrogen bond network and the stacking of molecules.

N-[3,5-bis(trifluoromethyl)phenyl]-3-methoxysalicylaldimine top

Crystal data top

C₁₆H₁₁F₆NO₂	F(000) = 736
M_r = 363.26	D_x = 1.618 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 35 reflections
a = 7.2130 (14) Å	θ = 5–25°
b = 29.196 (4) Å	µ = 0.16 mm⁻¹
c = 7.8870 (16) Å	T = 180 K
β = 116.140 (5)°	Plate, yellow
V = 1491.0 (5) Å³	0.20 × 0.20 × 0.01 mm
Z = 4

Data collection top

Siemens P4 diffractometer	R_int = 0.044
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 3.6°
Graphite monochromator	h = −8→8
ω scans	k = −34→34
17689 measured reflections	l = −9→9
2591 independent reflections	1 standard reflections every 120 min
1891 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)] = 0.070	H-atom parameters constrained
wR(F²) = 0.195	w = 1/[σ²(F_o²) + (0.0926P)² + ] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max = 0.060
2591 reflections	Δρ_max = 0.40 e Å⁻³
255 parameters	Δρ_min = −0.30 e Å⁻³
179 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0051 (3)

Crystal data top

C₁₆H₁₁F₆NO₂	V = 1491.0 (5) Å³
M_r = 363.26	Z = 4
Monoclinic, P2₁/a	Mo Kα radiation
a = 7.2130 (14) Å	µ = 0.16 mm⁻¹
b = 29.196 (4) Å	T = 180 K
c = 7.8870 (16) Å	0.20 × 0.20 × 0.01 mm
β = 116.140 (5)°

Data collection top

Siemens P4 diffractometer	R_int = 0.044
17689 measured reflections	1 standard reflections every 120 min
2591 independent reflections	intensity decay: none
1891 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.070	179 restraints
wR(F²) = 0.195	H-atom parameters constrained
S = 1.13	Δρ_max = 0.40 e Å⁻³
2591 reflections	Δρ_min = −0.30 e Å⁻³
255 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	Occ. (<1)
C11	0.5012 (5)	0.42955 (10)	0.2477 (5)	0.0494 (8)
C16	0.6443 (6)	0.46950 (12)	0.3042 (6)	0.0666 (10)
F4A	0.7690 (12)	0.4688 (2)	0.2219 (11)	0.095 (3)	0.616 (17)
F5A	0.7613 (10)	0.4715 (2)	0.4821 (9)	0.081 (2)	0.616 (17)
F6A	0.5399 (10)	0.5091 (2)	0.2567 (18)	0.116 (4)	0.616 (17)
F4B	0.8416 (13)	0.4581 (4)	0.360 (4)	0.161 (9)	0.384 (17)
F5B	0.652 (5)	0.4894 (7)	0.459 (3)	0.162 (8)	0.384 (17)
F6B	0.608 (2)	0.5015 (5)	0.1866 (16)	0.116 (6)	0.384 (17)
O1	0.4825 (3)	0.21511 (7)	0.3284 (3)	0.0472 (6)
H1	0.4534	0.2414	0.2894	0.071*
O2	0.6126 (4)	0.13593 (7)	0.4965 (3)	0.0589 (7)
N1	0.5042 (4)	0.30521 (8)	0.3468 (3)	0.0404 (6)
C1	0.8777 (5)	0.25443 (12)	0.7857 (5)	0.0530 (8)
H1A	0.9355	0.2814	0.8500	0.064*
C2	0.9467 (5)	0.21297 (14)	0.8728 (5)	0.0591 (10)
H2	1.0523	0.2120	0.9952	0.071*
C3	0.8608 (5)	0.17307 (13)	0.7802 (5)	0.0541 (9)
H3	0.9076	0.1452	0.8409	0.065*
C4	0.7063 (5)	0.17384 (10)	0.5987 (5)	0.0459 (8)
C5	0.6345 (4)	0.21577 (10)	0.5071 (4)	0.0400 (7)
C6	0.7209 (4)	0.25630 (10)	0.6010 (4)	0.0425 (7)
C7	0.6489 (5)	0.30035 (10)	0.5142 (4)	0.0435 (7)
H7	0.7106	0.3265	0.5832	0.052*
C8	0.7141 (7)	0.09310 (12)	0.5656 (6)	0.0729 (11)
H8A	0.6346	0.0689	0.4833	0.109*
H8B	0.7268	0.0878	0.6904	0.109*
H8C	0.8489	0.0939	0.5695	0.109*
C9	0.4415 (4)	0.34986 (9)	0.2761 (4)	0.0394 (7)
C10	0.5772 (5)	0.38647 (11)	0.3171 (5)	0.0481 (8)
H10	0.7180	0.3821	0.3905	0.058*
C12	0.2946 (5)	0.43644 (10)	0.1331 (4)	0.0489 (8)
H12	0.2452	0.4655	0.0873	0.059*
C13	0.1622 (4)	0.39965 (10)	0.0874 (4)	0.0430 (7)
C14	0.2343 (4)	0.35660 (10)	0.1592 (4)	0.0420 (7)
H14	0.1429	0.3321	0.1286	0.050*
C15	−0.0591 (5)	0.40608 (12)	−0.0418 (5)	0.0598 (9)
F1	−0.1019 (4)	0.39142 (11)	−0.2155 (4)	0.1065 (10)
F2	−0.1826 (3)	0.38267 (10)	0.0063 (4)	0.1091 (11)
F3	−0.1187 (4)	0.44886 (8)	−0.0660 (4)	0.1055 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C11	0.0527 (18)	0.0379 (18)	0.0528 (19)	−0.0082 (14)	0.0188 (16)	−0.0001 (14)
C16	0.063 (2)	0.050 (2)	0.074 (3)	−0.0132 (17)	0.019 (2)	0.0028 (18)
F4A	0.094 (5)	0.099 (5)	0.102 (5)	−0.045 (4)	0.052 (4)	−0.003 (3)
F5A	0.082 (4)	0.068 (4)	0.066 (3)	−0.033 (3)	0.008 (2)	−0.009 (2)
F6A	0.072 (3)	0.036 (2)	0.192 (9)	−0.012 (2)	0.013 (4)	0.008 (4)
F4B	0.072 (5)	0.094 (7)	0.26 (2)	−0.035 (4)	0.018 (8)	0.019 (9)
F5B	0.27 (2)	0.108 (12)	0.130 (10)	−0.120 (13)	0.112 (13)	−0.066 (9)
F6B	0.103 (9)	0.099 (9)	0.095 (6)	−0.062 (7)	−0.002 (5)	0.049 (6)
O1	0.0510 (12)	0.0376 (11)	0.0488 (13)	0.0070 (9)	0.0181 (10)	0.0019 (9)
O2	0.0706 (15)	0.0412 (13)	0.0665 (15)	0.0131 (11)	0.0319 (13)	0.0097 (11)
N1	0.0417 (13)	0.0362 (14)	0.0456 (15)	0.0002 (10)	0.0215 (12)	0.0002 (11)
C1	0.0461 (17)	0.063 (2)	0.0486 (19)	−0.0059 (15)	0.0195 (15)	0.0014 (16)
C2	0.0422 (17)	0.083 (3)	0.0482 (19)	0.0028 (17)	0.0159 (15)	0.0180 (19)
C3	0.0471 (17)	0.064 (2)	0.057 (2)	0.0133 (16)	0.0284 (16)	0.0226 (17)
C4	0.0469 (17)	0.0444 (18)	0.055 (2)	0.0078 (14)	0.0305 (16)	0.0074 (15)
C5	0.0330 (14)	0.0467 (17)	0.0421 (16)	0.0060 (12)	0.0181 (13)	0.0071 (13)
C6	0.0384 (15)	0.0510 (18)	0.0420 (16)	0.0018 (13)	0.0212 (13)	0.0031 (14)
C7	0.0446 (16)	0.0401 (17)	0.0500 (18)	−0.0041 (13)	0.0248 (15)	−0.0033 (14)
C8	0.091 (3)	0.049 (2)	0.090 (3)	0.026 (2)	0.050 (2)	0.022 (2)
C9	0.0448 (16)	0.0334 (15)	0.0426 (16)	0.0013 (12)	0.0217 (13)	−0.0012 (12)
C10	0.0435 (16)	0.0466 (18)	0.0525 (19)	−0.0054 (13)	0.0194 (14)	0.0017 (14)
C12	0.0571 (19)	0.0339 (16)	0.0516 (19)	−0.0006 (13)	0.0203 (16)	0.0008 (14)
C13	0.0451 (16)	0.0384 (16)	0.0427 (17)	0.0005 (13)	0.0167 (13)	−0.0023 (13)
C14	0.0443 (16)	0.0366 (16)	0.0433 (17)	−0.0054 (12)	0.0177 (13)	−0.0054 (13)
C15	0.0520 (19)	0.046 (2)	0.065 (2)	−0.0001 (16)	0.0111 (17)	−0.0034 (16)
F1	0.0835 (17)	0.132 (2)	0.0635 (16)	0.0026 (15)	−0.0051 (13)	−0.0167 (15)
F2	0.0465 (12)	0.119 (2)	0.139 (2)	−0.0020 (13)	0.0198 (14)	0.0519 (18)
F3	0.0679 (14)	0.0559 (15)	0.148 (3)	0.0164 (11)	0.0063 (15)	−0.0013 (15)

Geometric parameters (Å, º) top

C11—C12	1.375 (5)	C3—C4	1.373 (4)
C11—C10	1.385 (4)	C3—H3	0.9300
C11—C16	1.489 (5)	C4—C5	1.400 (4)
C16—F6B	1.260 (8)	C5—C6	1.390 (4)
C16—F5A	1.281 (7)	C6—C7	1.442 (4)
C16—F4A	1.322 (6)	C7—H7	0.9300
C16—F5B	1.328 (10)	C8—H8A	0.9600
C16—F4B	1.333 (9)	C8—H8B	0.9600
C16—F6A	1.340 (6)	C8—H8C	0.9600
O1—C5	1.352 (3)	C9—C14	1.382 (4)
O1—H1	0.8200	C9—C10	1.388 (4)
O2—C4	1.361 (4)	C10—H10	0.9300
O2—C8	1.430 (4)	C12—C13	1.376 (4)
N1—C7	1.280 (4)	C12—H12	0.9300
N1—C9	1.412 (4)	C13—C14	1.382 (4)
C1—C2	1.372 (5)	C13—C15	1.479 (4)
C1—C6	1.398 (4)	C14—H14	0.9300
C1—H1A	0.9300	C15—F2	1.305 (4)
C2—C3	1.369 (5)	C15—F3	1.307 (4)
C2—H2	0.9300	C15—F1	1.336 (4)

C12—C11—C10	121.2 (3)	C3—C4—C5	119.9 (3)
C12—C11—C16	119.3 (3)	O1—C5—C6	122.4 (3)
C10—C11—C16	119.5 (3)	O1—C5—C4	118.1 (3)
F6B—C16—F5A	126.5 (7)	C6—C5—C4	119.5 (3)
F6B—C16—F4A	67.3 (8)	C5—C6—C1	119.3 (3)
F5A—C16—F4A	106.0 (5)	C5—C6—C7	121.6 (3)
F6B—C16—F5B	105.3 (10)	C1—C6—C7	119.1 (3)
F5A—C16—F5B	39.9 (12)	N1—C7—C6	123.2 (3)
F4A—C16—F5B	133.9 (9)	N1—C7—H7	118.4
F6B—C16—F4B	105.8 (9)	C6—C7—H7	118.4
F5A—C16—F4B	63.7 (10)	O2—C8—H8A	109.5
F4A—C16—F4B	45.6 (10)	O2—C8—H8B	109.5
F5B—C16—F4B	101.3 (11)	H8A—C8—H8B	109.5
F6B—C16—F6A	41.0 (7)	O2—C8—H8C	109.5
F5A—C16—F6A	106.5 (6)	H8A—C8—H8C	109.5
F4A—C16—F6A	107.2 (6)	H8B—C8—H8C	109.5
F5B—C16—F6A	70.9 (11)	C14—C9—C10	119.4 (3)
F4B—C16—F6A	133.9 (6)	C14—C9—N1	117.3 (3)
F6B—C16—C11	117.9 (6)	C10—C9—N1	123.3 (3)
F5A—C16—C11	113.6 (4)	C9—C10—C11	119.5 (3)
F4A—C16—C11	111.9 (4)	C9—C10—H10	120.3
F5B—C16—C11	111.2 (7)	C11—C10—H10	120.3
F4B—C16—C11	113.7 (5)	C13—C12—C11	119.0 (3)
F6A—C16—C11	111.2 (4)	C13—C12—H12	120.5
C5—O1—H1	109.5	C11—C12—H12	120.5
C4—O2—C8	116.6 (3)	C12—C13—C14	120.7 (3)
C7—N1—C9	118.9 (3)	C12—C13—C15	119.7 (3)
C2—C1—C6	120.3 (3)	C14—C13—C15	119.6 (3)
C2—C1—H1A	119.8	C9—C14—C13	120.3 (3)
C6—C1—H1A	119.8	C9—C14—H14	119.9
C1—C2—C3	120.3 (3)	C13—C14—H14	119.9
C1—C2—H2	119.9	F2—C15—F3	108.7 (3)
C3—C2—H2	119.9	F2—C15—F1	104.6 (3)
C4—C3—C2	120.7 (3)	F3—C15—F1	104.1 (3)
C4—C3—H3	119.6	F2—C15—C13	113.6 (3)
C2—C3—H3	119.6	F3—C15—C13	114.1 (3)
O2—C4—C3	124.6 (3)	F1—C15—C13	110.9 (3)
O2—C4—C5	115.5 (3)

C12—C11—C16—F6B	−34.5 (13)	C2—C1—C6—C5	0.5 (4)
C10—C11—C16—F6B	147.9 (12)	C2—C1—C6—C7	178.9 (3)
C12—C11—C16—F5A	130.3 (5)	C9—N1—C7—C6	178.5 (3)
C10—C11—C16—F5A	−47.2 (6)	C5—C6—C7—N1	−0.7 (4)
C12—C11—C16—F4A	−109.6 (6)	C1—C6—C7—N1	−179.0 (3)
C10—C11—C16—F4A	72.8 (6)	C7—N1—C9—C14	−144.5 (3)
C12—C11—C16—F5B	87.1 (16)	C7—N1—C9—C10	36.1 (4)
C10—C11—C16—F5B	−90.4 (16)	C14—C9—C10—C11	3.1 (5)
C12—C11—C16—F4B	−159.3 (14)	N1—C9—C10—C11	−177.5 (3)
C10—C11—C16—F4B	23.2 (14)	C12—C11—C10—C9	−2.4 (5)
C12—C11—C16—F6A	10.2 (9)	C16—C11—C10—C9	175.1 (3)
C10—C11—C16—F6A	−167.3 (7)	C10—C11—C12—C13	0.0 (5)
C6—C1—C2—C3	−0.8 (5)	C16—C11—C12—C13	−177.5 (3)
C1—C2—C3—C4	0.7 (5)	C11—C12—C13—C14	1.7 (5)
C8—O2—C4—C3	−15.4 (4)	C11—C12—C13—C15	−177.6 (3)
C8—O2—C4—C5	165.0 (3)	C10—C9—C14—C13	−1.5 (4)
C2—C3—C4—O2	−180.0 (3)	N1—C9—C14—C13	179.1 (3)
C2—C3—C4—C5	−0.4 (5)	C12—C13—C14—C9	−0.9 (5)
O2—C4—C5—O1	−0.5 (4)	C15—C13—C14—C9	178.3 (3)
C3—C4—C5—O1	179.9 (3)	C12—C13—C15—F2	−141.0 (3)
O2—C4—C5—C6	179.8 (2)	C14—C13—C15—F2	39.7 (5)
C3—C4—C5—C6	0.1 (4)	C12—C13—C15—F3	−15.6 (5)
O1—C5—C6—C1	−180.0 (2)	C14—C13—C15—F3	165.1 (3)
C4—C5—C6—C1	−0.2 (4)	C12—C13—C15—F1	101.5 (4)
O1—C5—C6—C7	1.7 (4)	C14—C13—C15—F1	−77.7 (4)
C4—C5—C6—C7	−178.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.91	2.635 (3)	146
C7—H7···F1ⁱ	0.93	2.46	3.387 (4)	175

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₁F₆NO₂
M_r	363.26
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	180
a, b, c (Å)	7.2130 (14), 29.196 (4), 7.8870 (16)
β (°)	116.140 (5)
V (Å³)	1491.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.20 × 0.20 × 0.01

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	17689, 2591, 1891
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.195, 1.13
No. of reflections	2591
No. of parameters	255
No. of restraints	179
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.30

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

O1—C5	1.352 (3)	N1—C7	1.280 (4)
O2—C4	1.361 (4)	N1—C9	1.412 (4)
O2—C8	1.430 (4)	C6—C7	1.442 (4)

C12—C11—C16	119.3 (3)	C5—C6—C7	121.6 (3)
C10—C11—C16	119.5 (3)	C1—C6—C7	119.1 (3)
C4—O2—C8	116.6 (3)	N1—C7—C6	123.2 (3)
C7—N1—C9	118.9 (3)	C14—C9—N1	117.3 (3)
O2—C4—C5	115.5 (3)	C10—C9—N1	123.3 (3)
O1—C5—C6	122.4 (3)	C12—C13—C15	119.7 (3)
O1—C5—C4	118.1 (3)	C14—C13—C15	119.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.91	2.635 (3)	146
C7—H7···F1ⁱ	0.93	2.46	3.387 (4)	175

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

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