(E)-(2,5-Difluoro­benz­yl)[(2-eth­oxy­naphthalen-1-yl)methyl­idene]amine

Pekdemir, M.; Işık, Ş.; Macit, M.; Alaman Ağar, A.; Soylu, M.S.

doi:10.1107/S1600536813001967

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o361

doi:10.1107/S1600536813001967

Open

access

(E)-(2,5-Difluorobenzyl)[(2-ethoxynaphthalen-1-yl)methylidene]amine

Merve Pekdemir,^a ^* Şamil Işık,^a Mustafa Macit,^b Ayşen Alaman Ağar ^b and Mustafa Serkan Soylu ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Kurupelit, TR-55139 Samsun, Turkey, ^bDepartment of Chemistry, Art and Science Faculty, Ondokuz Mayıs University, Kurupelit, TR-55139 Samsun, Turkey, and ^cGiresun University, Arts and Science Faculty, Department of Physics, Giresun, Turkey
^*Correspondence e-mail: merve.pekdemir@oposta.omu.edu.tr

(Received 20 December 2012; accepted 19 January 2013; online 9 February 2013)

In the title molecule, C₂₀H₁₇F₂NO, which adopts an E conformation with respect to the imine C=N double bond, the mean planes of the naphthalene ring system and the difluorophenyl ring form a dihedral angle of 85.82 (7)°. An intramolecular C—H⋯N hydrogen bond occurs. In the crystal, weak C—H⋯F hydrogen bonds link the molecules into zigzag chains along [010].

Related literature

For structural studies of Schiff bases by our group, see: Gül et al. (2007 ); Kantar et al. (2012 ); Kargılı et al. (2012 ); Pekdemir et al. (2012 ); Vesek et al. (2012 ). For classification of hydrogen-bonding patterns, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₇F₂NO
M_r = 325.35
Monoclinic, P 2₁ /c
a = 12.5963 (8) Å
b = 14.3010 (8) Å
c = 9.8693 (8) Å
β = 108.672 (8)°
V = 1684.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.25 mm

Data collection

Oxford Diffraction SuperNova Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.703, T_max = 1.000
5942 measured reflections
2958 independent reflections
1997 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.151
S = 1.06
2958 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.18 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
C3—H3⋯N1	0.93	2.32	2.955 (3)	125
C6—H6⋯F1ⁱ	0.93	2.61	3.505 (4)	162
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813001967/cv5376sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813001967/cv5376Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813001967/cv5376Isup3.cml

checkCIF report

Comment top

In continuation of our structural study of Schiff bases (Gül et al., 2007; Kantar et al., 2012; Pekdemir et al., 2012; Vesek et al., 2012), herewith we present the title compound, (I).

In (I) (Fig. 1), the C13═N1 bond distance of 1.262 (3) Å is shorter than the standart 1.28 Å value of C═N double bond, similar to the corresponding bond distance in (E)—N-[(2- ethoxynaphthalen-1-yl)methylidene]-2-ethylaniline [1.261 (3) Å; Kargılı et al.,2012]. The dihedral angle between the naphthalene ring system and the benzene ring is 85.82 (7)°. The C13—N1—C14—C15 torsion angle is 179.4 (3)°. The molecular conformation is supported by an intramolecular C—H···N hydrogen bond, which generates S(6) ring (Bernstein et al., 1995).

In the crystal, weak intermolecular C—H···F hydrogen bonds (Table 1) link the molecules into zigzag chains in [010] (Fig. 2).

Related literature top

For structural studies of Schiff bases by our group, see: Gül et al. (2007); Kantar et al. (2012); Kargılı et al. (2012); Pekdemir et al. (2012); Vesek et al. (2012). For classification of hydrogen-bonding patterns, see: Bernstein et al. (1995).

Experimental top

(E)-1-(2,5-difluorophenyl)-N-((2-ethoxynaphthalen-1-yl) methylene)methanamine was prepared by refluxing a mixture of a solution containing 2-ethoxy-1-naphthaldehyde (20.0 mg, 0.1 mmol) in ethanol (20 ml) and a solution containing 2,5-difluorobenzylamine (14.3 mg, 0.1 mmol) in ethanol (20 ml). The reaction mixture was stirred for 5 h under reflux. Single crystals of the title compound for X-ray analysis were obtained by slow evaporation of an ethanol solution (Yield 74%; m.p.356 - 358 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability. Dashed line denotes hydrogen bond.
	Fig. 2. A portion of the crystal packing showing weak intermolecular C—H···F hydrogen bonds as dashed lines.

(E)-(2,5-Difluorobenzyl)[(2-ethoxynaphthalen-1-yl)methylidene]amine top

Crystal data top

C₂₀H₁₇F₂NO	F(000) = 680
M_r = 325.35	D_x = 1.283 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1869 reflections
a = 12.5963 (8) Å	θ = 3.3–29.3°
b = 14.3010 (8) Å	µ = 0.09 mm⁻¹
c = 9.8693 (8) Å	T = 293 K
β = 108.672 (8)°	Block, yellow
V = 1684.3 (2) Å³	0.30 × 0.25 × 0.25 mm
Z = 4

Data collection top

Oxford Diffraction SuperNova Eos diffractometer	2958 independent reflections
Radiation source: fine-focus sealed tube	1997 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 16.0454 pixels mm^-1	θ_max = 25.0°, θ_min = 3.3°
ω scans	h = −13→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −17→17
T_min = 0.703, T_max = 1.000	l = −11→11
5942 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0491P)² + 0.5882P] where P = (F_o² + 2F_c²)/3
2958 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₁₇F₂NO	V = 1684.3 (2) Å³
M_r = 325.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.5963 (8) Å	µ = 0.09 mm⁻¹
b = 14.3010 (8) Å	T = 293 K
c = 9.8693 (8) Å	0.30 × 0.25 × 0.25 mm
β = 108.672 (8)°

Data collection top

Oxford Diffraction SuperNova Eos diffractometer	2958 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	1997 reflections with I > 2σ(I)
T_min = 0.703, T_max = 1.000	R_int = 0.018
5942 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.06	Δρ_max = 0.18 e Å⁻³
2958 reflections	Δρ_min = −0.18 e Å⁻³
217 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	0.05443 (18)	0.09513 (16)	0.9269 (2)	0.0475 (6)
C2	−0.04096 (19)	0.08982 (16)	0.8003 (3)	0.0505 (6)
C3	−0.0486 (2)	0.02790 (19)	0.6849 (3)	0.0648 (7)
H3	0.0107	−0.0121	0.6900	0.078*
C4	−0.1420 (3)	0.0264 (2)	0.5666 (3)	0.0792 (9)
H4	−0.1445	−0.0140	0.4918	0.095*
C5	−0.2335 (2)	0.0840 (2)	0.5559 (3)	0.0802 (9)
H5	−0.2967	0.0816	0.4750	0.096*
C6	−0.2300 (2)	0.1434 (2)	0.6633 (3)	0.0690 (8)
H6	−0.2917	0.1812	0.6561	0.083*
C7	−0.1346 (2)	0.14949 (18)	0.7868 (3)	0.0558 (6)
C8	−0.1289 (2)	0.2129 (2)	0.8967 (3)	0.0669 (7)
H8	−0.1897	0.2520	0.8879	0.080*
C9	−0.0383 (2)	0.21936 (19)	1.0152 (3)	0.0657 (7)
H9	−0.0369	0.2628	1.0859	0.079*
C10	0.0540 (2)	0.15986 (17)	1.0311 (3)	0.0529 (6)
C11	0.1491 (2)	0.2230 (2)	1.2652 (3)	0.0759 (8)
H11A	0.0884	0.2049	1.3004	0.091*
H11B	0.1386	0.2879	1.2353	0.091*
C12	0.2588 (3)	0.2110 (2)	1.3797 (3)	0.0938 (10)
H12A	0.2606	0.2491	1.4604	0.141*
H12B	0.3182	0.2296	1.3441	0.141*
H12C	0.2685	0.1466	1.4084	0.141*
C13	0.15149 (19)	0.03193 (16)	0.9571 (3)	0.0515 (6)
H13	0.1901	0.0185	1.0524	0.062*
C14	0.2785 (2)	−0.07076 (19)	0.9136 (3)	0.0690 (8)
H14A	0.2510	−0.1338	0.8875	0.083*
H14B	0.3083	−0.0676	1.0171	0.083*
C15	0.37095 (19)	−0.05036 (18)	0.8517 (3)	0.0578 (7)
C16	0.4542 (2)	−0.1146 (2)	0.8634 (3)	0.0749 (8)
C17	0.5395 (3)	−0.1034 (3)	0.8079 (4)	0.0963 (11)
H17	0.5931	−0.1499	0.8179	0.116*
C18	0.5443 (3)	−0.0221 (3)	0.7371 (4)	0.1016 (12)
H18	0.6008	−0.0124	0.6967	0.122*
C19	0.4647 (3)	0.0442 (3)	0.7271 (4)	0.0894 (10)
C20	0.3785 (2)	0.0321 (2)	0.7833 (3)	0.0738 (8)
H20	0.3259	0.0792	0.7750	0.089*
F1	0.45086 (15)	−0.19516 (13)	0.9363 (3)	0.1126 (7)
F2	0.46988 (19)	0.12570 (19)	0.6602 (3)	0.1524 (10)
N1	0.18605 (17)	−0.00533 (16)	0.8631 (2)	0.0647 (6)
O1	0.14961 (14)	0.16450 (12)	1.14686 (18)	0.0653 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0479 (13)	0.0437 (13)	0.0606 (14)	0.0002 (11)	0.0309 (11)	0.0012 (11)
C2	0.0504 (13)	0.0479 (13)	0.0615 (14)	−0.0059 (11)	0.0294 (11)	0.0034 (12)
C3	0.0580 (15)	0.0659 (17)	0.0731 (17)	−0.0086 (13)	0.0248 (13)	−0.0090 (14)
C4	0.0711 (19)	0.086 (2)	0.079 (2)	−0.0214 (17)	0.0224 (16)	−0.0187 (17)
C5	0.0602 (18)	0.094 (2)	0.080 (2)	−0.0175 (17)	0.0126 (15)	0.0027 (19)
C6	0.0533 (15)	0.0746 (18)	0.0803 (19)	−0.0004 (14)	0.0233 (14)	0.0203 (17)
C7	0.0538 (14)	0.0550 (15)	0.0662 (15)	0.0011 (12)	0.0299 (12)	0.0122 (13)
C8	0.0624 (16)	0.0677 (18)	0.0804 (19)	0.0171 (14)	0.0367 (15)	0.0094 (15)
C9	0.0726 (18)	0.0666 (17)	0.0673 (17)	0.0152 (15)	0.0356 (15)	−0.0071 (14)
C10	0.0554 (14)	0.0545 (15)	0.0566 (14)	0.0043 (12)	0.0289 (12)	0.0005 (12)
C11	0.083 (2)	0.080 (2)	0.0684 (18)	0.0049 (16)	0.0296 (15)	−0.0219 (16)
C12	0.091 (2)	0.105 (3)	0.079 (2)	0.006 (2)	0.0167 (17)	−0.0266 (19)
C13	0.0515 (13)	0.0468 (14)	0.0621 (14)	−0.0025 (11)	0.0265 (11)	−0.0008 (12)
C14	0.0623 (16)	0.0550 (16)	0.098 (2)	0.0051 (13)	0.0371 (15)	−0.0117 (15)
C15	0.0460 (13)	0.0582 (15)	0.0671 (16)	−0.0007 (12)	0.0152 (11)	−0.0197 (13)
C16	0.0596 (17)	0.0640 (18)	0.106 (2)	0.0023 (15)	0.0332 (16)	−0.0129 (17)
C17	0.0589 (19)	0.105 (3)	0.135 (3)	0.0102 (19)	0.044 (2)	−0.017 (2)
C18	0.062 (2)	0.142 (4)	0.112 (3)	−0.005 (2)	0.0430 (19)	−0.001 (3)
C19	0.067 (2)	0.103 (3)	0.096 (2)	−0.0109 (19)	0.0223 (17)	0.017 (2)
C20	0.0589 (16)	0.076 (2)	0.0832 (19)	0.0036 (15)	0.0179 (15)	−0.0035 (16)
F1	0.0883 (13)	0.0712 (12)	0.192 (2)	0.0199 (10)	0.0639 (14)	0.0089 (13)
F2	0.1138 (17)	0.161 (2)	0.186 (2)	−0.0072 (16)	0.0539 (17)	0.078 (2)
N1	0.0534 (12)	0.0723 (15)	0.0744 (14)	0.0099 (11)	0.0288 (11)	−0.0132 (12)
O1	0.0654 (11)	0.0716 (12)	0.0626 (11)	0.0083 (9)	0.0257 (9)	−0.0139 (9)

Geometric parameters (Å, º) top

C1—C10	1.385 (3)	C11—H11B	0.9700
C1—C2	1.432 (3)	C12—H12A	0.9600
C1—C13	1.472 (3)	C12—H12B	0.9600
C2—C3	1.421 (3)	C12—H12C	0.9600
C2—C7	1.427 (3)	C13—N1	1.262 (3)
C3—C4	1.366 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—N1	1.452 (3)
C4—C5	1.394 (4)	C14—C15	1.507 (3)
C4—H4	0.9300	C14—H14A	0.9700
C5—C6	1.348 (4)	C14—H14B	0.9700
C5—H5	0.9300	C15—C16	1.371 (3)
C6—C7	1.414 (3)	C15—C20	1.377 (4)
C6—H6	0.9300	C16—C17	1.363 (4)
C7—C8	1.398 (4)	C16—F1	1.366 (3)
C8—C9	1.351 (4)	C17—C18	1.368 (5)
C8—H8	0.9300	C17—H17	0.9300
C9—C10	1.408 (3)	C18—C19	1.361 (5)
C9—H9	0.9300	C18—H18	0.9300
C10—O1	1.371 (3)	C19—F2	1.352 (4)
C11—O1	1.438 (3)	C19—C20	1.379 (4)
C11—C12	1.489 (4)	C20—H20	0.9300
C11—H11A	0.9700

C10—C1—C2	118.8 (2)	C11—C12—H12A	109.5
C10—C1—C13	117.4 (2)	C11—C12—H12B	109.5
C2—C1—C13	123.7 (2)	H12A—C12—H12B	109.5
C3—C2—C7	117.1 (2)	C11—C12—H12C	109.5
C3—C2—C1	123.7 (2)	H12A—C12—H12C	109.5
C7—C2—C1	119.2 (2)	H12B—C12—H12C	109.5
C4—C3—C2	120.9 (3)	N1—C13—C1	124.7 (2)
C4—C3—H3	119.5	N1—C13—H13	117.6
C2—C3—H3	119.5	C1—C13—H13	117.6
C3—C4—C5	121.3 (3)	N1—C14—C15	112.0 (2)
C3—C4—H4	119.3	N1—C14—H14A	109.2
C5—C4—H4	119.3	C15—C14—H14A	109.2
C6—C5—C4	119.7 (3)	N1—C14—H14B	109.2
C6—C5—H5	120.2	C15—C14—H14B	109.2
C4—C5—H5	120.2	H14A—C14—H14B	107.9
C5—C6—C7	121.4 (3)	C16—C15—C20	116.4 (3)
C5—C6—H6	119.3	C16—C15—C14	120.4 (3)
C7—C6—H6	119.3	C20—C15—C14	123.3 (2)
C8—C7—C6	121.8 (2)	C17—C16—F1	118.2 (3)
C8—C7—C2	118.7 (2)	C17—C16—C15	124.6 (3)
C6—C7—C2	119.6 (2)	F1—C16—C15	117.3 (3)
C9—C8—C7	122.4 (2)	C16—C17—C18	118.4 (3)
C9—C8—H8	118.8	C16—C17—H17	120.8
C7—C8—H8	118.8	C18—C17—H17	120.8
C8—C9—C10	119.6 (2)	C19—C18—C17	118.5 (3)
C8—C9—H9	120.2	C19—C18—H18	120.8
C10—C9—H9	120.2	C17—C18—H18	120.8
O1—C10—C1	116.1 (2)	F2—C19—C18	119.1 (3)
O1—C10—C9	122.5 (2)	F2—C19—C20	118.2 (3)
C1—C10—C9	121.4 (2)	C18—C19—C20	122.7 (3)
O1—C11—C12	107.7 (2)	C15—C20—C19	119.5 (3)
O1—C11—H11A	110.2	C15—C20—H20	120.3
C12—C11—H11A	110.2	C19—C20—H20	120.3
O1—C11—H11B	110.2	C13—N1—C14	116.6 (2)
C12—C11—H11B	110.2	C10—O1—C11	118.26 (19)
H11A—C11—H11B	108.5

C10—C1—C2—C3	178.3 (2)	C8—C9—C10—C1	0.6 (4)
C13—C1—C2—C3	−5.1 (3)	C10—C1—C13—N1	−153.0 (2)
C10—C1—C2—C7	−1.6 (3)	C2—C1—C13—N1	30.4 (3)
C13—C1—C2—C7	175.0 (2)	N1—C14—C15—C16	−166.9 (2)
C7—C2—C3—C4	0.1 (4)	N1—C14—C15—C20	14.0 (4)
C1—C2—C3—C4	−179.8 (2)	C20—C15—C16—C17	−2.6 (4)
C2—C3—C4—C5	−1.1 (4)	C14—C15—C16—C17	178.3 (3)
C3—C4—C5—C6	0.7 (5)	C20—C15—C16—F1	177.2 (2)
C4—C5—C6—C7	0.8 (4)	C14—C15—C16—F1	−1.9 (4)
C5—C6—C7—C8	178.0 (3)	F1—C16—C17—C18	−178.8 (3)
C5—C6—C7—C2	−1.8 (4)	C15—C16—C17—C18	1.0 (5)
C3—C2—C7—C8	−178.5 (2)	C16—C17—C18—C19	0.9 (5)
C1—C2—C7—C8	1.4 (3)	C17—C18—C19—F2	178.6 (3)
C3—C2—C7—C6	1.3 (3)	C17—C18—C19—C20	−1.1 (5)
C1—C2—C7—C6	−178.8 (2)	C16—C15—C20—C19	2.2 (4)
C6—C7—C8—C9	179.9 (3)	C14—C15—C20—C19	−178.7 (3)
C2—C7—C8—C9	−0.3 (4)	F2—C19—C20—C15	179.8 (3)
C7—C8—C9—C10	−0.8 (4)	C18—C19—C20—C15	−0.5 (5)
C2—C1—C10—O1	−177.18 (19)	C1—C13—N1—C14	−175.9 (2)
C13—C1—C10—O1	6.1 (3)	C15—C14—N1—C13	−130.8 (2)
C2—C1—C10—C9	0.6 (3)	C1—C10—O1—C11	−173.3 (2)
C13—C1—C10—C9	−176.2 (2)	C9—C10—O1—C11	9.0 (3)
C8—C9—C10—O1	178.2 (2)	C12—C11—O1—C10	176.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1	0.93	2.32	2.955 (3)	125
C6—H6···F1ⁱ	0.93	2.61	3.505 (4)	162

Symmetry code: (i) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇F₂NO
M_r	325.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.5963 (8), 14.3010 (8), 9.8693 (8)
β (°)	108.672 (8)
V (Å³)	1684.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Oxford Diffraction SuperNova Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.703, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5942, 2958, 1997
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.151, 1.06
No. of reflections	2958
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1	0.93	2.32	2.955 (3)	125
C6—H6···F1ⁱ	0.93	2.61	3.505 (4)	162

Symmetry code: (i) −x, y+1/2, −z+3/2.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gül, Z. S., Erşahin, F., Ağar, E. & Işık, Ş. (2007). Acta Cryst. E63, o2902. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kantar, E. N., Köysal, Y., Gümüş, S., Ağar, E. & Soylu, M. S. (2012). Acta Cryst. E68, o1587. CSD CrossRef IUCr Journals Google Scholar
Kargılı, H., Macit, M., Alpaslan, G., Kazak, C. & Erdönmez, A. (2012). Acta Cryst. E68, o3176. CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Pekdemir, M., Işık, Ş. & Alaman Ağar, A. (2012). Acta Cryst. E68, o2148. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vesek, H., Kazak, C., Alaman Ağar, A., Macit, M. & Soylu, M. S. (2012). Acta Cryst. E68, o2518. CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o361

doi:10.1107/S1600536813001967

Open

access