4-(4-Fluoro­phen­yl)-1-phenyl-3-(pyridin-4-yl)-1H-pyrazol-5-amine

Abu Thaher, B.; Koch, P.; Schollmeyer, D.; Laufer, S.

doi:10.1107/S1600536812004096

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o632

doi:10.1107/S1600536812004096

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4-(4-Fluorophenyl)-1-phenyl-3-(pyridin-4-yl)-1H-pyrazol-5-amine

Bassam Abu Thaher,^a Pierre Koch,^b Dieter Schollmeyer ^c and Stefan Laufer ^b ^*

^aFaculty of Science, Chemistry Department, Islamic University of Gaza, Gaza Strip, Palestinian Territories, ^bInstitute of Pharmacy, Department of Pharmaceutical and Medicinal Chemistry, Eberhard Karls University Tübingen, Auf der Morgenstelle 8, 72076 Tübingen, Germany, and ^cDepartment of Organic Chemistry, Johannes Gutenberg University Mainz, Duesbergweg 10-14, D-55099 Mainz, Germany
^*Correspondence e-mail: stefan.laufer@uni-tuebingen.de

(Received 30 January 2012; accepted 31 January 2012; online 10 February 2012)

In the title compound, C₂₀H₁₅FN₄, the pyrazole ring forms dihedral angles of 43.51 (6), 39.95 (6) and 32.23 (6)° with the directly attached 4-fluorophenyl, pyridine and phenyl rings, respectively. The crystal packing is stabilized by intermolecular N—H⋯N and N—H⋯F hydrogen bonds.

Related literature

For p38α MAP kinase inhibitors having a vicinal 4-fluorophenyl/pyridin-4-yl system connected to a five-membered heterocyclic core, see: Abu Thaher et al. (2009 ); Peifer et al. (2006 ). For inhibitory activity and preparation of the title compound, see: Abu Thaher et al. (2012 ).

Experimental

Crystal data

C₂₀H₁₅FN₄
M_r = 330.36
Monoclinic, P 2₁ /n
a = 12.2408 (3) Å
b = 10.4427 (2) Å
c = 12.9099 (3) Å
β = 101.951 (1)°
V = 1614.46 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 193 K
0.39 × 0.38 × 0.24 mm

Data collection

Bruker SMART CCD diffractometer
29688 measured reflections
5459 independent reflections
3972 reflections with I > 2σ(I)
R_int = 0.092

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.139
S = 1.07
5459 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N25—H25A⋯N15ⁱ	0.85	2.18	2.9866 (13)	158
N25—H25B⋯F24ⁱⁱ	0.86	2.44	3.0631 (11)	130
Symmetry codes: (i) x, y-1, z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812004096/bt5808sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004096/bt5808Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812004096/bt5808Isup3.cml

checkCIF report

Comment top

Compounds having a vicinal 4-fluorophenyl/pyridin-4-yl system connected to a five-membered heterocyclic core have been considered to be potential p38α MAP kinase inhibitors (Abu Thaher et al. 2009, Peifer et al. 2006). Recently, we showed that the regioisomeric switch from 3-(4-fluorophenyl)-4-(pyridin-4-yl)-1-(aryl)-1H-pyrazol-5-amine to 4-(4-fluorophenyl)-3-(pyridin-4-yl)-1-(aryl)-1H-pyrazol-5-amine completely changed the inhibitory profile from p38α MAP kinase to kinases releant in cancer (Abu Thaher et al. 2012).

In the crystal structure of the title compound (Fig. 1), the pyrazole ring forms dihedral angels of 43.51 (6)°, 39.95 (6)° and 32.23 (6)° with the 4-fluorophenyl, pyridine and phenyl rings, respectively. The 4-fluorophenyl ring encloses dihedral angels of 46.49 (6)° and 17.4 (6)° toward the pyridine and phenyl rings, respectively. The pyridine ring is orientated at a dihedral angle of 30.07 (6)° toward the phenyl ring.

The crystal packing shows that the amino function acts as a hydrogen bond donor of two intermolecular hydrogen bonds - one to the nitrogen atom (N15) of the pyridine ring and another one to the fluorine atom (F24) of the 4-fluorophenyl ring of two different molecules. The length of the hydrogen bonds is 2.18 Å and 2.44 Å, respectively.

Related literature top

For p38α MAP kinase inhibitors having a vicinal 4-fluorophenyl/pyridin-4-yl system connected to a five-membered heterocyclic core, see: Abu Thaher et al. (2009); Peifer et al. (2006). For inhibitory activity and preparation of the title compound, see: Abu Thaher et al. (2012).

Experimental top

LDA (20 mmol) was added to 30 ml dry THF and cooled to 195 K. 4-Fluorophenyl acetonitrile (14 mmol) in 10 ml THF was added dropwise and the reaction was stirred for 45 min. N-Phenyl-4-pyridinecarbohydrazonoyl chloride (5 mmol) dissolved in THF was added slowly to the reaction and stirring was continued for 1 h. After warming to 293 K, water (50 ml) was added and the reaction mixture was extracted with ethyl acetate (2x 50 ml). The organic layer was dried over Na₂SO₄, concentrated to about 5 ml and the pure product precipitated as a pale brown solid, filtered and washed with petroleum ether. Yield: 30%. Crystals suitable for X-Ray were obtained from recrystallization from hot methanol.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: APEX2 (Bruker, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. View of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are depicted as circles of arbitrary size.

4-(4-Fluorophenyl)-1-phenyl-3-(pyridin-4-yl)-1H-pyrazol-5-amine top

Crystal data top

C₂₀H₁₅FN₄	F(000) = 688
M_r = 330.36	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8198 reflections
a = 12.2408 (3) Å	θ = 2.5–31°
b = 10.4427 (2) Å	µ = 0.09 mm⁻¹
c = 12.9099 (3) Å	T = 193 K
β = 101.951 (1)°	Plate, colourless
V = 1614.46 (6) Å³	0.39 × 0.38 × 0.24 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3972 reflections with I > 2σ(I)
Radiation source: sealed Tube	R_int = 0.092
Graphite monochromator	θ_max = 31.7°, θ_min = 2.1°
CCD scan	h = −17→18
29688 measured reflections	k = −15→15
5459 independent reflections	l = −19→19

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0759P)²] where P = (F_o² + 2F_c²)/3
5459 reflections	(Δ/σ)_max = 0.001
226 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₀H₁₅FN₄	V = 1614.46 (6) Å³
M_r = 330.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.2408 (3) Å	µ = 0.09 mm⁻¹
b = 10.4427 (2) Å	T = 193 K
c = 12.9099 (3) Å	0.39 × 0.38 × 0.24 mm
β = 101.951 (1)°

Data collection top

Bruker SMART CCD diffractometer	3972 reflections with I > 2σ(I)
29688 measured reflections	R_int = 0.092
5459 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.07	Δρ_max = 0.43 e Å⁻³
5459 reflections	Δρ_min = −0.24 e Å⁻³
226 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
N1	0.42742 (8)	0.43838 (8)	0.21818 (7)	0.01963 (19)
N2	0.42901 (8)	0.56672 (8)	0.24356 (7)	0.0203 (2)
C3	0.38505 (9)	0.62463 (9)	0.15232 (8)	0.0186 (2)
C4	0.35487 (9)	0.53683 (9)	0.06717 (8)	0.0188 (2)
C5	0.38251 (9)	0.41737 (9)	0.11336 (8)	0.0196 (2)
C6	0.47171 (9)	0.34914 (9)	0.29983 (8)	0.0200 (2)
C7	0.52687 (9)	0.23961 (10)	0.27749 (9)	0.0253 (2)
H7	0.5349	0.2224	0.2072	0.030*
C8	0.57028 (11)	0.15549 (11)	0.35910 (10)	0.0310 (3)
H8	0.6058	0.0789	0.3440	0.037*
C9	0.56218 (11)	0.18236 (11)	0.46214 (10)	0.0323 (3)
H9	0.5923	0.1245	0.5175	0.039*
C10	0.50995 (10)	0.29421 (12)	0.48467 (9)	0.0290 (3)
H10	0.5067	0.3143	0.5557	0.035*
C11	0.46249 (10)	0.37644 (10)	0.40313 (9)	0.0243 (2)
H11	0.4239	0.4510	0.4179	0.029*
C12	0.37406 (8)	0.76535 (9)	0.15138 (8)	0.0193 (2)
C13	0.34059 (10)	0.82967 (10)	0.23403 (9)	0.0235 (2)
H13	0.3249	0.7833	0.2926	0.028*
C14	0.33030 (10)	0.96196 (10)	0.23020 (10)	0.0276 (3)
H14	0.3088	1.0042	0.2880	0.033*
N15	0.34895 (9)	1.03314 (9)	0.14963 (8)	0.0298 (2)
C16	0.38196 (11)	0.97073 (11)	0.07086 (10)	0.0299 (3)
H16	0.3964	1.0196	0.0131	0.036*
C17	0.39641 (10)	0.83907 (10)	0.06831 (9)	0.0258 (2)
H17	0.4211	0.7999	0.0108	0.031*
C18	0.30291 (9)	0.56329 (9)	−0.04437 (8)	0.0193 (2)
C19	0.21579 (9)	0.65213 (10)	−0.06991 (9)	0.0238 (2)
H19	0.1874	0.6914	−0.0146	0.029*
C20	0.17003 (10)	0.68406 (11)	−0.17433 (9)	0.0273 (3)
H20	0.1119	0.7456	−0.1910	0.033*
C21	0.21154 (10)	0.62388 (11)	−0.25283 (9)	0.0276 (3)
C22	0.29435 (10)	0.53254 (11)	−0.23223 (9)	0.0269 (2)
H22	0.3194	0.4908	−0.2884	0.032*
C23	0.34046 (9)	0.50288 (10)	−0.12725 (9)	0.0229 (2)
H23	0.3982	0.4408	−0.1116	0.027*
F24	0.16930 (7)	0.65754 (7)	−0.35554 (6)	0.0425 (2)
N25	0.37049 (9)	0.29779 (8)	0.06845 (7)	0.0264 (2)
H25A	0.3602	0.2335	0.1059	0.040*
H25B	0.3307	0.3008	0.0053	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0270 (5)	0.0128 (4)	0.0171 (4)	0.0019 (3)	−0.0001 (3)	−0.0001 (3)
N2	0.0273 (5)	0.0125 (4)	0.0195 (4)	0.0005 (3)	0.0010 (3)	−0.0006 (3)
C3	0.0216 (5)	0.0137 (4)	0.0197 (5)	0.0004 (4)	0.0024 (4)	−0.0001 (3)
C4	0.0219 (5)	0.0147 (4)	0.0184 (5)	0.0008 (4)	0.0010 (4)	0.0006 (3)
C5	0.0238 (5)	0.0150 (4)	0.0186 (5)	0.0005 (4)	0.0014 (4)	−0.0006 (3)
C6	0.0232 (5)	0.0149 (4)	0.0195 (5)	0.0000 (4)	−0.0008 (4)	0.0032 (3)
C7	0.0293 (6)	0.0213 (5)	0.0230 (5)	0.0043 (4)	0.0002 (4)	0.0003 (4)
C8	0.0342 (6)	0.0212 (5)	0.0335 (7)	0.0082 (5)	−0.0024 (5)	0.0023 (4)
C9	0.0372 (7)	0.0264 (6)	0.0282 (6)	0.0021 (5)	−0.0047 (5)	0.0098 (5)
C10	0.0357 (6)	0.0289 (6)	0.0205 (5)	−0.0018 (5)	0.0016 (5)	0.0048 (4)
C11	0.0298 (6)	0.0203 (5)	0.0218 (5)	0.0016 (4)	0.0035 (4)	0.0013 (4)
C12	0.0206 (5)	0.0135 (4)	0.0216 (5)	0.0005 (4)	−0.0008 (4)	0.0000 (3)
C13	0.0293 (6)	0.0169 (4)	0.0234 (5)	0.0018 (4)	0.0038 (4)	0.0008 (4)
C14	0.0329 (6)	0.0178 (5)	0.0314 (6)	0.0025 (4)	0.0054 (5)	−0.0033 (4)
N15	0.0364 (6)	0.0164 (4)	0.0342 (6)	0.0003 (4)	0.0018 (4)	0.0003 (4)
C16	0.0412 (7)	0.0171 (5)	0.0303 (6)	−0.0028 (5)	0.0047 (5)	0.0056 (4)
C17	0.0360 (6)	0.0181 (5)	0.0232 (6)	−0.0016 (4)	0.0063 (5)	0.0003 (4)
C18	0.0214 (5)	0.0152 (4)	0.0196 (5)	−0.0018 (4)	0.0002 (4)	0.0008 (3)
C19	0.0253 (5)	0.0203 (5)	0.0235 (5)	0.0024 (4)	0.0002 (4)	−0.0003 (4)
C20	0.0276 (6)	0.0222 (5)	0.0276 (6)	0.0018 (4)	−0.0044 (5)	0.0035 (4)
C21	0.0331 (6)	0.0269 (5)	0.0187 (5)	−0.0057 (5)	−0.0044 (4)	0.0045 (4)
C22	0.0326 (6)	0.0280 (5)	0.0196 (5)	−0.0029 (5)	0.0042 (4)	−0.0011 (4)
C23	0.0244 (5)	0.0203 (5)	0.0230 (5)	0.0010 (4)	0.0031 (4)	0.0003 (4)
F24	0.0545 (5)	0.0467 (5)	0.0197 (4)	−0.0003 (4)	−0.0078 (3)	0.0087 (3)
N25	0.0409 (6)	0.0144 (4)	0.0202 (5)	−0.0002 (4)	−0.0025 (4)	−0.0008 (3)

Geometric parameters (Å, º) top

N1—C5	1.3687 (13)	C13—C14	1.3871 (14)
N1—N2	1.3789 (11)	C13—H13	0.9500
N1—C6	1.4272 (13)	C14—N15	1.3360 (16)
N2—C3	1.3342 (13)	C14—H14	0.9500
C3—C4	1.4202 (13)	N15—C16	1.3389 (17)
C3—C12	1.4755 (13)	C16—C17	1.3875 (15)
C4—C5	1.3938 (13)	C16—H16	0.9500
C4—C18	1.4748 (13)	C17—H17	0.9500
C5—N25	1.3718 (12)	C18—C23	1.3992 (15)
C6—C7	1.3885 (15)	C18—C19	1.4004 (14)
C6—C11	1.3910 (16)	C19—C20	1.3891 (15)
C7—C8	1.3900 (15)	C19—H19	0.9500
C7—H7	0.9500	C20—C21	1.3760 (17)
C8—C9	1.3830 (19)	C20—H20	0.9500
C8—H8	0.9500	C21—F24	1.3658 (12)
C9—C10	1.3909 (17)	C21—C22	1.3771 (17)
C9—H9	0.9500	C22—C23	1.3909 (15)
C10—C11	1.3891 (15)	C22—H22	0.9500
C10—H10	0.9500	C23—H23	0.9500
C11—H11	0.9500	N25—H25A	0.8520
C12—C13	1.3924 (15)	N25—H25B	0.8591
C12—C17	1.3925 (15)

C5—N1—N2	111.95 (8)	C14—C13—C12	119.48 (11)
C5—N1—C6	129.72 (8)	C14—C13—H13	120.3
N2—N1—C6	118.33 (8)	C12—C13—H13	120.3
C3—N2—N1	104.32 (8)	N15—C14—C13	123.58 (11)
N2—C3—C4	112.55 (9)	N15—C14—H14	118.2
N2—C3—C12	118.56 (9)	C13—C14—H14	118.2
C4—C3—C12	128.89 (9)	C14—N15—C16	116.59 (10)
C5—C4—C3	104.21 (9)	N15—C16—C17	124.09 (11)
C5—C4—C18	127.07 (9)	N15—C16—H16	118.0
C3—C4—C18	128.70 (9)	C17—C16—H16	118.0
N1—C5—N25	123.35 (9)	C16—C17—C12	118.90 (11)
N1—C5—C4	106.96 (8)	C16—C17—H17	120.6
N25—C5—C4	129.69 (10)	C12—C17—H17	120.6
C7—C6—C11	120.49 (10)	C23—C18—C19	118.25 (10)
C7—C6—N1	120.74 (10)	C23—C18—C4	121.24 (9)
C11—C6—N1	118.72 (9)	C19—C18—C4	120.50 (10)
C6—C7—C8	119.29 (11)	C20—C19—C18	121.46 (11)
C6—C7—H7	120.4	C20—C19—H19	119.3
C8—C7—H7	120.4	C18—C19—H19	119.3
C9—C8—C7	120.56 (11)	C21—C20—C19	117.96 (10)
C9—C8—H8	119.7	C21—C20—H20	121.0
C7—C8—H8	119.7	C19—C20—H20	121.0
C8—C9—C10	119.94 (10)	F24—C21—C20	118.31 (11)
C8—C9—H9	120.0	F24—C21—C22	118.77 (11)
C10—C9—H9	120.0	C20—C21—C22	122.92 (10)
C11—C10—C9	119.93 (11)	C21—C22—C23	118.44 (11)
C11—C10—H10	120.0	C21—C22—H22	120.8
C9—C10—H10	120.0	C23—C22—H22	120.8
C10—C11—C6	119.71 (11)	C22—C23—C18	120.90 (10)
C10—C11—H11	120.1	C22—C23—H23	119.6
C6—C11—H11	120.1	C18—C23—H23	119.6
C13—C12—C17	117.35 (9)	C5—N25—H25A	119.6
C13—C12—C3	121.00 (9)	C5—N25—H25B	111.0
C17—C12—C3	121.66 (10)	H25A—N25—H25B	116.5

C5—N1—N2—C3	−0.46 (12)	N1—C6—C11—C10	−176.75 (10)
C6—N1—N2—C3	178.81 (9)	N2—C3—C12—C13	−40.18 (15)
N1—N2—C3—C4	−0.21 (12)	C4—C3—C12—C13	139.92 (12)
N1—N2—C3—C12	179.88 (9)	N2—C3—C12—C17	139.91 (11)
N2—C3—C4—C5	0.76 (13)	C4—C3—C12—C17	−39.99 (17)
C12—C3—C4—C5	−179.34 (11)	C17—C12—C13—C14	0.40 (16)
N2—C3—C4—C18	179.05 (10)	C3—C12—C13—C14	−179.51 (10)
C12—C3—C4—C18	−1.05 (19)	C12—C13—C14—N15	1.25 (18)
N2—N1—C5—N25	−179.34 (10)	C13—C14—N15—C16	−1.73 (18)
C6—N1—C5—N25	1.49 (18)	C14—N15—C16—C17	0.61 (18)
N2—N1—C5—C4	0.95 (13)	N15—C16—C17—C12	0.97 (19)
C6—N1—C5—C4	−178.22 (11)	C13—C12—C17—C16	−1.43 (16)
C3—C4—C5—N1	−0.99 (12)	C3—C12—C17—C16	178.48 (10)
C18—C4—C5—N1	−179.31 (10)	C5—C4—C18—C23	−45.51 (16)
C3—C4—C5—N25	179.33 (12)	C3—C4—C18—C23	136.58 (12)
C18—C4—C5—N25	1.0 (2)	C5—C4—C18—C19	135.85 (12)
C5—N1—C6—C7	33.57 (17)	C3—C4—C18—C19	−42.06 (16)
N2—N1—C6—C7	−145.55 (10)	C23—C18—C19—C20	−2.48 (16)
C5—N1—C6—C11	−148.95 (11)	C4—C18—C19—C20	176.19 (10)
N2—N1—C6—C11	31.93 (15)	C18—C19—C20—C21	1.16 (17)
C11—C6—C7—C8	1.73 (17)	C19—C20—C21—F24	−178.07 (10)
N1—C6—C7—C8	179.17 (10)	C19—C20—C21—C22	1.21 (18)
C6—C7—C8—C9	−2.19 (18)	F24—C21—C22—C23	177.17 (10)
C7—C8—C9—C10	0.18 (19)	C20—C21—C22—C23	−2.11 (18)
C8—C9—C10—C11	2.31 (19)	C21—C22—C23—C18	0.67 (17)
C9—C10—C11—C6	−2.76 (18)	C19—C18—C23—C22	1.54 (16)
C7—C6—C11—C10	0.74 (17)	C4—C18—C23—C22	−177.13 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N25—H25A···N15ⁱ	0.85	2.18	2.9866 (13)	158
N25—H25B···F24ⁱⁱ	0.86	2.44	3.0631 (11)	130

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅FN₄
M_r	330.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	193
a, b, c (Å)	12.2408 (3), 10.4427 (2), 12.9099 (3)
β (°)	101.951 (1)
V (Å³)	1614.46 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.39 × 0.38 × 0.24

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	29688, 5459, 3972
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.740

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.139, 1.07
No. of reflections	5459
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.24

Computer programs: APEX2 (Bruker, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N25—H25A···N15ⁱ	0.85	2.18	2.9866 (13)	158
N25—H25B···F24ⁱⁱ	0.86	2.44	3.0631 (11)	130

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

Acknowledgements

BAT thanks the Alexander von Humboldt Foundation for funding.

References

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