1-[4-Chloro-3-(trifluoro­meth­yl)phen­yl]-4-phenyl-1H-1,2,3-triazole

Altimari, J.M.; Healy, P.C.; Henderson, L.C.

doi:10.1107/S1600536812042705

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3159

doi:10.1107/S1600536812042705

Open

access

1-[4-Chloro-3-(trifluoromethyl)phenyl]-4-phenyl-1H-1,2,3-triazole

Jarrad M. Altimari,^a Peter C. Healy ^b ^* and Luke C. Henderson ^c

^aSRC for Biotechnology, Chemistry and Systems Biology, Faculty of Science and Technology, Deakin University, Vic, 3216, Australia, ^bQueensland Micro and Nanotechnology Centre, Griffith University, Brisbane 4111, Australia, and ^cInstitute for Frontier Materials, SRC for Biotechnology, Chemistry and Systems Biology, Faculty of Science and Technology, Deakin University, Vic, 3216, Australia
^*Correspondence e-mail: P.Healy@griffith.edu.au

(Received 11 October 2012; accepted 12 October 2012; online 20 October 2012)

In the title compound, C₁₅H₉ClF₃N₃, the phenyl and chloro-trifluoromethyl benzene rings are twisted with respect to the planar triazole group, making dihedral angles of 21.29 (12) and 32.19 (11)°, respectively. In the crystal, the molecules pack in a head-to-tail arrangement along the a axis with closest inter-centroid distances between the triazole rings of 3.7372 (12) Å.

Related literature

For background to the synthesis of N-aryl-1,2,3-triazoles, see: Bock et al. (2006 ); Irie et al. (2012 ). For biological background, see: Jia & Zhu (2010 ); Henderson et al. (2012 ); Alam et al. (2006 , 2007 ). For related structures, see: Lin et al. (2008 ); Lin (2010 ).

Experimental

Crystal data

C₁₅H₉ClF₃N₃
M_r = 323.70
Monoclinic, C 2/c
a = 30.7475 (16) Å
b = 5.8877 (3) Å
c = 15.4364 (8) Å
β = 105.470 (5)°
V = 2693.2 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 249 K
0.33 × 0.26 × 0.24 mm

Data collection

Oxford Diffraction GEMINI S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ), T_min = 0.902, T_max = 0.928
3934 measured reflections
2355 independent reflections
1899 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.091
S = 1.07
2355 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO; program(s) used to solve structure: TEXSAN (Molecular Structure Corporation, 2001 ) and SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: TEXSAN and SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812042705/tk5159sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042705/tk5159Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812042705/tk5159Isup3.cml

checkCIF report

Comment top

The structure of the title compound, (I), was determined as part of an ongoing project developing N-aryl-1,2,3-triazoles as amide mimetics for medicinal applications. The synthesis of 1,2,3-triazoles via copper mediated 1,3-dipolar reactions has become one of the most widely used methodologies to tether molecules together or to a surface (Bock et al., 2006; Irie et al., 2012). Electronically deactivated N-phenyl-1,2,3-triazoles have been employed in several areas such as the combinatorial development of kinase inhibitors (Jia & Zhu, 2010) in the development of monoamine oxidase inhibitors, androgen receptor antagonists (Henderson et al., 2012) and as GABA receptor antagonists (Alam et al., 2006; Alam et al., 2007). This compound provides an aryl chloride moiety in the para-position relative to the triazole ring providing a synthetic handle for further structural elaboration.

In the molecular structure of (I) (Fig. 1) the planar phenyl and chloro-trifluoromethyl benzene rings are twisted with respect to the central planar triazole group with dihedral angles of 21.29 (12) and 32.19 (11)°, respectively. In the triazole ring, the N1—N2 and N2—N3 bond lengths are 1.357 (3) and 1.310 (3) Å, respectively. and are similar to those reported for related compounds (Lin et al., 2008; Lin, 2010). In the crystal lattice, the molecules stack in a head to tail arrangement along the a axis (Fig. 2) with the centroid-centroid distances between the triazole rings 4.1494 (12) and 3.7372 (12) Å.

Related literature top

For background to the synthesis of N-aryl-1,2,3-triazoles, see: Bock et al. (2006); Irie et al. (2012). For biological background, see: Jia & Zhu (2010); Henderson et al. (2012); Alam et al. (2006, 2007). For related structures, see: Lin et al. (2008); Lin (2010).

Experimental top

Phenyl acetylene (127 mg, 1.25 mmol, 1 eq), 4-azido-1-chloro-2-(trifluoromethyl) benzene (230 mg, 1.04 mmol, 1 eq) and copper(I) chloride (10 mg, 10 mol%) were stirred in water (3 ml) for 10 min. The solution was then stirred under microwave irradiation at 100°C for 30 min in a sealed vessel. The solution cooled to room temperature, dichloromethane (3 ml) was added and the biphasic mixture stirred for 3 min. The aqueous phase was then extracted using dichloromethane (2 x 10 ml), the combined organic layers were washed with HCl (4M, 5 ml), NaOH (1M, 5 ml), water (5 ml). The organic phase dried over MgSO₄, filtered and concentrated under vacuum. The solution was then taken up in chloroform and allowed to slowly evaporate. ν (max) cm^-1 3124, 1495, 1310, 1147, 1037. ¹H NMR (400 MHz, CDCl₃): δ = 9.50 (1H, s, triazole H), 8.42 (1H, s, ArH), 8.32 (1H, dd, J = 8.7, 2.6 Hz, ArH), 8.02 (1H, d, J = 8.7 Hz, ArH), 7.95 (2H, d, J = 8 Hz, ArH), 7.51 (2H, m, ArH), 7.40 (1H, m, ArH). ¹³C NMR (100 MHz, CDCl₃): δ = 148.22, 136.16, 133.98, 130.91 (m), 130.47, 129.65, 129.04, 128.53 (q, J²_C—F = 32 Hz), 125.93, 125.70 (m), 122.89 (q, J¹_C—F = 272 Hz), 120.62, 119.75. M.pt: 443–445.3 K. HRMS, m/z calcd for(C₁₅H₉ClF₃N₃) 324.05099, found 324.05011.

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: TEXSAN (Molecular Structure Corporation, 2001) and SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 2001) and SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labelling and displacement ellipsoids for non-H atoms drawn at the 40% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. Molecular packing of the title compound viewed along [0 1 0].

1-[4-Chloro-3-(trifluoromethyl)phenyl]-4-phenyl-1H-1,2,3-triazole top

Crystal data top

C₁₅H₉ClF₃N₃	F(000) = 1312
M_r = 323.70	D_x = 1.597 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 1854 reflections
a = 30.7475 (16) Å	θ = 3.4–30.3°
b = 5.8877 (3) Å	µ = 0.32 mm⁻¹
c = 15.4364 (8) Å	T = 249 K
β = 105.470 (5)°	Block, colourless
V = 2693.2 (2) Å³	0.33 × 0.26 × 0.24 mm
Z = 8

Data collection top

Oxford Diffraction GEMINI S Ultra diffractometer	2355 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1899 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 16.0774 pixels mm^-1	θ_max = 25.0°, θ_min = 3.4°
ω and ϕ scans	h = −36→33
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012),	k = −5→6
T_min = 0.902, T_max = 0.928	l = −9→18
3934 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0327P)² + 2.2063P] where P = (F_o² + 2F_c²)/3
2355 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₉ClF₃N₃	V = 2693.2 (2) Å³
M_r = 323.70	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 30.7475 (16) Å	µ = 0.32 mm⁻¹
b = 5.8877 (3) Å	T = 249 K
c = 15.4364 (8) Å	0.33 × 0.26 × 0.24 mm
β = 105.470 (5)°

Data collection top

Oxford Diffraction GEMINI S Ultra diffractometer	2355 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012),	1899 reflections with I > 2σ(I)
T_min = 0.902, T_max = 0.928	R_int = 0.021
3934 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.07	Δρ_max = 0.18 e Å⁻³
2355 reflections	Δρ_min = −0.22 e Å⁻³
199 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl1	0.78052 (2)	0.33228 (12)	0.32573 (4)	0.0454 (2)
F1	0.76886 (4)	0.0366 (3)	0.48769 (11)	0.0575 (6)
F2	0.78035 (5)	−0.1587 (3)	0.37911 (10)	0.0587 (5)
F3	0.81441 (4)	−0.2452 (3)	0.51428 (10)	0.0522 (5)
N1	0.96027 (6)	0.1414 (3)	0.56964 (11)	0.0285 (6)
N2	0.97402 (6)	−0.0774 (3)	0.58511 (13)	0.0369 (6)
N3	1.01508 (6)	−0.0729 (3)	0.63832 (12)	0.0358 (6)
C4	1.02780 (7)	0.1481 (4)	0.65769 (13)	0.0276 (7)
C5	0.99302 (7)	0.2849 (4)	0.61383 (14)	0.0281 (7)
C11	0.91648 (7)	0.1919 (4)	0.51321 (13)	0.0275 (6)
C12	0.88165 (7)	0.0422 (4)	0.51110 (13)	0.0281 (7)
C13	0.83879 (7)	0.0861 (4)	0.45597 (13)	0.0277 (7)
C14	0.83212 (7)	0.2782 (4)	0.40213 (13)	0.0293 (7)
C15	0.86683 (7)	0.4302 (4)	0.40630 (14)	0.0335 (7)
C16	0.90929 (7)	0.3881 (4)	0.46234 (14)	0.0324 (7)
C17	0.80065 (7)	−0.0695 (4)	0.45873 (15)	0.0365 (8)
C41	1.07225 (7)	0.2101 (4)	0.71678 (13)	0.0276 (7)
C42	1.10818 (7)	0.0584 (4)	0.73080 (14)	0.0344 (7)
C43	1.15027 (7)	0.1168 (5)	0.78475 (15)	0.0394 (8)
C44	1.15723 (8)	0.3258 (5)	0.82582 (15)	0.0398 (8)
C45	1.12182 (8)	0.4780 (5)	0.81243 (14)	0.0389 (8)
C46	1.07966 (7)	0.4216 (4)	0.75828 (14)	0.0333 (7)
H5	0.99210	0.43430	0.61430	0.0340*
H12	0.88700	−0.09090	0.54740	0.0330*
H15	0.86140	0.56400	0.37040	0.0400*
H16	0.93320	0.49300	0.46580	0.0390*
H42	1.10380	−0.08670	0.70260	0.0410*
H43	1.17450	0.01160	0.79350	0.0470*
H44	1.18610	0.36500	0.86340	0.0480*
H45	1.12650	0.62270	0.84080	0.0470*
H46	1.05570	0.52790	0.74940	0.0400*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0334 (3)	0.0438 (4)	0.0481 (3)	0.0047 (3)	−0.0079 (3)	0.0048 (3)
F1	0.0322 (7)	0.0558 (11)	0.0906 (11)	−0.0039 (8)	0.0271 (8)	−0.0025 (9)
F2	0.0579 (9)	0.0458 (10)	0.0574 (9)	−0.0175 (8)	−0.0109 (7)	−0.0089 (8)
F3	0.0371 (8)	0.0447 (10)	0.0679 (9)	−0.0101 (7)	0.0019 (7)	0.0210 (8)
N1	0.0223 (9)	0.0286 (11)	0.0336 (9)	0.0001 (8)	0.0055 (7)	0.0002 (8)
N2	0.0283 (10)	0.0288 (12)	0.0489 (11)	−0.0018 (9)	0.0020 (9)	−0.0005 (9)
N3	0.0257 (9)	0.0317 (12)	0.0447 (11)	0.0000 (9)	0.0003 (8)	0.0003 (9)
C4	0.0243 (11)	0.0294 (13)	0.0300 (11)	−0.0012 (10)	0.0087 (9)	0.0004 (10)
C5	0.0246 (11)	0.0266 (13)	0.0331 (11)	−0.0036 (10)	0.0077 (9)	−0.0017 (10)
C11	0.0225 (10)	0.0309 (13)	0.0288 (10)	−0.0002 (10)	0.0066 (9)	−0.0014 (10)
C12	0.0260 (11)	0.0294 (13)	0.0280 (10)	0.0024 (10)	0.0058 (9)	0.0011 (10)
C13	0.0255 (11)	0.0288 (13)	0.0286 (11)	−0.0020 (10)	0.0068 (9)	−0.0048 (9)
C14	0.0264 (11)	0.0326 (14)	0.0276 (11)	0.0034 (10)	0.0051 (9)	−0.0022 (10)
C15	0.0341 (12)	0.0321 (14)	0.0346 (12)	0.0041 (11)	0.0096 (10)	0.0064 (10)
C16	0.0274 (11)	0.0332 (14)	0.0372 (12)	−0.0039 (10)	0.0099 (10)	0.0015 (10)
C17	0.0263 (11)	0.0368 (15)	0.0419 (13)	−0.0019 (11)	0.0012 (10)	0.0003 (12)
C41	0.0262 (11)	0.0310 (13)	0.0259 (10)	−0.0011 (10)	0.0075 (9)	0.0030 (10)
C42	0.0306 (11)	0.0335 (14)	0.0373 (12)	0.0007 (11)	0.0059 (10)	0.0005 (11)
C43	0.0284 (12)	0.0453 (17)	0.0417 (13)	0.0045 (12)	0.0044 (10)	0.0083 (12)
C44	0.0305 (12)	0.0508 (17)	0.0324 (12)	−0.0082 (13)	−0.0016 (10)	0.0047 (12)
C45	0.0422 (13)	0.0381 (15)	0.0323 (12)	−0.0082 (12)	0.0026 (10)	−0.0042 (11)
C46	0.0332 (12)	0.0345 (14)	0.0315 (11)	0.0031 (11)	0.0076 (10)	0.0002 (10)

Geometric parameters (Å, º) top

Cl1—C14	1.735 (2)	C15—C16	1.383 (3)
F1—C17	1.334 (3)	C41—C42	1.392 (3)
F2—C17	1.329 (3)	C41—C46	1.391 (3)
F3—C17	1.338 (3)	C42—C43	1.383 (3)
N1—N2	1.357 (3)	C43—C44	1.375 (4)
N1—C5	1.352 (3)	C44—C45	1.382 (4)
N1—C11	1.426 (3)	C45—C46	1.383 (3)
N2—N3	1.310 (3)	C5—H5	0.8800
N3—C4	1.369 (3)	C12—H12	0.9500
C4—C5	1.366 (3)	C15—H15	0.9500
C4—C41	1.473 (3)	C16—H16	0.9500
C11—C12	1.381 (3)	C42—H42	0.9500
C11—C16	1.381 (3)	C43—H43	0.9500
C12—C13	1.389 (3)	C44—H44	0.9500
C13—C14	1.386 (3)	C45—H45	0.9500
C13—C17	1.498 (3)	C46—H46	0.9500
C14—C15	1.381 (3)

Cl1···F1	3.1445 (18)	C41···H15^x	3.0300
Cl1···F2	3.0063 (19)	C42···H45^vi	3.0400
Cl1···F2ⁱ	3.1086 (19)	C42···H15^x	3.0100
Cl1···F2ⁱⁱ	3.2167 (16)	C43···H15^x	2.9900
F1···Cl1	3.1445 (18)	C44···H15^x	3.0000
F1···F1ⁱⁱⁱ	2.835 (2)	C45···H42ⁱ	3.0400
F1···F3^iv	3.075 (2)	C45···H15^x	3.0100
F2···Cl1^v	3.2167 (16)	C46···H5	3.0000
F2···Cl1^vi	3.1085 (19)	C46···H15^x	3.0300
F2···Cl1	3.0063 (19)	H5···N2ⁱ	2.9400
F3···C45^vii	3.295 (3)	H5···C16	2.9800
F3···C15^vi	3.235 (3)	H5···C46	3.0000
F3···F1^iv	3.075 (2)	H5···H16	2.5400
F1···H44^viii	2.8100	H5···H46	2.5100
F3···H45^vii	2.6000	H12···F3	2.3400
F3···H12	2.3400	H12···N2	2.5800
N2···H5^vi	2.9400	H12···H45^vii	2.5300
N2···H12	2.5800	H15···C41^x	3.0300
N3···H42	2.6400	H15···C42^x	3.0100
C5···C46^ix	3.449 (3)	H15···C43^x	2.9900
C12···C43^ix	3.569 (3)	H15···C44^x	3.0000
C12···C44^ix	3.487 (3)	H15···C45^x	3.0100
C15···C45^x	3.527 (3)	H15···C46^x	3.0300
C15···C46^x	3.486 (3)	H16···C5	2.8000
C15···F3ⁱ	3.235 (3)	H16···H5	2.5400
C43···C12^ix	3.569 (3)	H42···N3	2.6400
C44···C12^ix	3.487 (3)	H42···C45^vi	3.0400
C45···F3^xi	3.295 (3)	H42···C14^xii	3.0800
C45···C15^x	3.527 (3)	H42···C15^xii	2.9200
C46···C5^ix	3.449 (3)	H42···C16^xii	3.0400
C46···C15^x	3.486 (3)	H44···F1^xiii	2.8100
C5···H16	2.8000	H45···C42ⁱ	3.0400
C5···H46	2.8300	H45···F3^xi	2.6000
C14···H42^xii	3.0800	H45···H12^xi	2.5300
C15···H42^xii	2.9200	H46···C5	2.8300
C16···H42^xii	3.0400	H46···H5	2.5100
C16···H5	2.9800

N2—N1—C5	110.45 (18)	C4—C41—C42	120.3 (2)
N2—N1—C11	120.29 (18)	C4—C41—C46	121.2 (2)
C5—N1—C11	129.26 (19)	C42—C41—C46	118.5 (2)
N1—N2—N3	107.10 (17)	C41—C42—C43	120.7 (2)
N2—N3—C4	109.13 (17)	C42—C43—C44	120.4 (2)
N3—C4—C5	108.19 (19)	C43—C44—C45	119.5 (2)
N3—C4—C41	122.3 (2)	C44—C45—C46	120.6 (2)
C5—C4—C41	129.5 (2)	C41—C46—C45	120.4 (2)
N1—C5—C4	105.1 (2)	N1—C5—H5	127.00
N1—C11—C12	118.77 (19)	C4—C5—H5	127.00
N1—C11—C16	120.2 (2)	C11—C12—H12	120.00
C12—C11—C16	121.0 (2)	C13—C12—H12	120.00
C11—C12—C13	119.9 (2)	C14—C15—H15	120.00
C12—C13—C14	118.9 (2)	C16—C15—H15	120.00
C12—C13—C17	119.4 (2)	C11—C16—H16	120.00
C14—C13—C17	121.63 (19)	C15—C16—H16	120.00
Cl1—C14—C13	121.30 (17)	C41—C42—H42	120.00
Cl1—C14—C15	117.89 (17)	C43—C42—H42	120.00
C13—C14—C15	120.8 (2)	C42—C43—H43	120.00
C14—C15—C16	120.1 (2)	C44—C43—H43	120.00
C11—C16—C15	119.1 (2)	C43—C44—H44	120.00
F1—C17—F2	106.84 (18)	C45—C44—H44	120.00
F1—C17—F3	106.38 (18)	C44—C45—H45	120.00
F1—C17—C13	111.87 (19)	C46—C45—H45	120.00
F2—C17—F3	106.10 (19)	C41—C46—H46	120.00
F2—C17—C13	113.17 (18)	C45—C46—H46	120.00
F3—C17—C13	112.02 (18)

C5—N1—N2—N3	−0.2 (2)	C11—C12—C13—C17	−176.1 (2)
C11—N1—N2—N3	179.82 (18)	C12—C13—C14—C15	−3.3 (3)
N2—N1—C5—C4	−0.1 (2)	C17—C13—C14—Cl1	−7.2 (3)
C11—N1—C5—C4	179.94 (19)	C12—C13—C17—F1	116.4 (2)
N2—N1—C11—C12	32.1 (3)	C12—C13—C17—F2	−122.9 (2)
N2—N1—C11—C16	−148.4 (2)	C17—C13—C14—C15	174.3 (2)
C5—N1—C11—C12	−147.9 (2)	C12—C13—C14—Cl1	175.22 (16)
C5—N1—C11—C16	31.6 (3)	C14—C13—C17—F2	59.6 (3)
N1—N2—N3—C4	0.4 (2)	C14—C13—C17—F3	179.48 (19)
N2—N3—C4—C5	−0.4 (2)	C12—C13—C17—F3	−3.0 (3)
N2—N3—C4—C41	179.51 (19)	C14—C13—C17—F1	−61.2 (3)
C41—C4—C5—N1	−179.6 (2)	Cl1—C14—C15—C16	−176.31 (17)
N3—C4—C5—N1	0.3 (2)	C13—C14—C15—C16	2.2 (3)
C5—C4—C41—C42	−158.3 (2)	C14—C15—C16—C11	0.5 (3)
C5—C4—C41—C46	20.4 (3)	C4—C41—C42—C43	178.7 (2)
N3—C4—C41—C46	−159.5 (2)	C42—C41—C46—C45	−0.3 (3)
N3—C4—C41—C42	21.9 (3)	C46—C41—C42—C43	0.0 (3)
C16—C11—C12—C13	1.2 (3)	C4—C41—C46—C45	−179.0 (2)
N1—C11—C12—C13	−179.29 (19)	C41—C42—C43—C44	0.3 (3)
N1—C11—C16—C15	178.24 (19)	C42—C43—C44—C45	−0.3 (4)
C12—C11—C16—C15	−2.2 (3)	C43—C44—C45—C46	0.0 (4)
C11—C12—C13—C14	1.6 (3)	C44—C45—C46—C41	0.3 (3)

Symmetry codes: (i) x, y+1, z; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+3/2, −y+1/2, −z+1; (iv) −x+3/2, −y−1/2, −z+1; (v) −x+3/2, y−1/2, −z+1/2; (vi) x, y−1, z; (vii) −x+2, y−1, −z+3/2; (viii) x−1/2, −y+1/2, z−1/2; (ix) −x+2, y, −z+3/2; (x) −x+2, −y+1, −z+1; (xi) −x+2, y+1, −z+3/2; (xii) −x+2, −y, −z+1; (xiii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₉ClF₃N₃
M_r	323.70
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	249
a, b, c (Å)	30.7475 (16), 5.8877 (3), 15.4364 (8)
β (°)	105.470 (5)
V (Å³)	2693.2 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.33 × 0.26 × 0.24

Data collection
Diffractometer	Oxford Diffraction GEMINI S Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012),
T_min, T_max	0.902, 0.928
No. of measured, independent and observed [I > 2σ(I)] reflections	3934, 2355, 1899
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.091, 1.07
No. of reflections	2355
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.22

Computer programs: CrysAlis PRO (Agilent, 2012), TEXSAN (Molecular Structure Corporation, 2001) and SIR97 (Altomare et al., 1999), TEXSAN (Molecular Structure Corporation, 2001) and SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009).

Acknowledgements

We acknowledge support of this work by Griffith University, the Queensland University of Technology, the Strategic Research Center for Biotechnology, Chemistry and Systems Biology and the Institute for Frontier Materials Deakin University.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Alam, M. S., Kajiki, R., Hanatani, H., Kong, X., Ozoe, F., Matsui, Y., Matsumura, F. & Ozoe, Y. (2006). J. Agric. Food Chem. 54, 1361–1372. Web of Science CrossRef PubMed CAS Google Scholar
Alam, M. S., Ozoe, F., Matsumura, F. & Ozoe, Y. (2007). Bioorg. Med. Chem. 15, 5090–5104. Web of Science CrossRef PubMed CAS Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bock, V. D., Hiemstra, H. & van Maarseveen, J. H. (2006). Eur. J. Org. Chem. pp. 51–68. Web of Science CrossRef Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Henderson, L. C., Altimari, J. M., Dyson, G., Servinis, L., Niranjan, B. & Risbridger, G. P. (2012). Bioorg. Chem. 40, 1–5. Web of Science CrossRef CAS PubMed Google Scholar
Irie, T., Fujii, I. & Sawa, M. (2012). Bioorg. Med. Chem. Lett. 22, 591–596. Web of Science CrossRef CAS PubMed Google Scholar
Jia, Z. & Zhu, Q. (2010). Bioorg. Med. Chem. Lett. 20, 6222–6225. Web of Science CrossRef CAS PubMed Google Scholar
Lin, J. R. (2010). Acta Cryst. E66, o1967. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lin, J. R., Yao, J. Y. & Zhao, H. (2008). Acta Cryst. E64, o1843. Web of Science CSD CrossRef IUCr Journals Google Scholar
Molecular Structure Corporation. (2001). TEXSAN for Windows. MSC, 9009 New Trails Drive, The Woodlands, TX 77381, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar