1-(4-Fluoro­phen­yl)-5-(4-methoxy­phen­yl)pyrazolidin-3-one

Dai, B.-J.; Liu, Y.-Y.; Xu, Q.-B.; Hu, J.; Zhu, H.-J.

doi:10.1107/S1600536809007144

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o675

doi:10.1107/S1600536809007144

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1-(4-Fluorophenyl)-5-(4-methoxyphenyl)pyrazolidin-3-one

Bao-Jiang Dai,^a Yuan-Yuan Liu,^b Qing-Bing Xu,^b Jing Hu ^b and Hong-Jun Zhu ^b ^*

^aNantong Jiangshan Agrochemical & Chemicals Co Ltd, Nantong 226006, People's Republic of China, and ^bDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: zhuhj@njut.edu.cn

(Received 25 February 2009; accepted 26 February 2009; online 6 March 2009)

In the molecule of the title compound, C₁₆H₁₅FN₂O₂, the benzene rings are oriented at a dihedral angle of 88.61 (3)°. The five-membered ring adopts an envelope conformation. Intramolecular C—H⋯N hydrogen bonds result in the formation of two planar five-membered rings. In the crystal structure, intermolecular N—H⋯O and C—H⋯F hydrogen bonds link the molecules, forming R₂²(8) and R₂²(18) ring motifs. Weak C—H⋯π interactions may further stabilize the structure.

Related literature

For applications of pyrazolidin-3-one, see: Prakash et al. (2008 ); Nonaka (2003 ); Mabuchi & Ohtsuka (1999 ). For a related structure, see: Liu et al. (2008 ). For bond-length data, see: Allen et al. (1987 ). For ring motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₅FN₂O₂
M_r = 286.30
Monoclinic, P 2₁ /c
a = 11.455 (2) Å
b = 7.1590 (14) Å
c = 18.136 (4) Å
β = 101.05 (3)°
V = 1459.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 K
0.4 × 0.4 × 0.3 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.969, T_max = 0.991
2991 measured reflections
2844 independent reflections
1869 reflections with I > 2σ(I)
R_int = 0.023
3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.164
S = 1.01
2844 reflections
191 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
N2—H2A⋯O1ⁱ	0.86	1.98	2.838 (2)	175
C5—H5A⋯N2	0.93	2.43	2.747 (3)	100
C8—H8A⋯Fⁱⁱ	0.97	2.45	3.388 (3)	164
C11—H11A⋯N1	0.93	2.53	2.885 (3)	103
C2—H2B⋯Cg2ⁱⁱⁱ	0.93	2.71	3.589 (3)	157
C15—H15A⋯Cg1^iv	0.93	2.89	3.801 (3)	167
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x, y+1, z. Cg1 and Cg2 are centroids of the C1–C6 andC10–C15 rings, respectively.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809007144/hk2631sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007144/hk2631Isup2.hkl

checkCIF report

Comment top

Nowadays, pyrazolidin-3-one and its derivatives used as pesticide have been developed most quickly, such as antiseptic (Prakash et al., 2008), insecticide (Nonaka, 2003) and herbicide (Mabuchi & Ohtsuka, 1999). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (C1-C6) and C (C10-C15) are, of course, planar, and they are oriented at a dihedral angle of 88.61 (3)°. The five-membered ring B (N1/N2/C7-C9) adopts envelope conformation with C7 atom displaced by 0.363 (3) Å from the plane of the other ring atoms. The intramolecular C-H···N hydrogen bonds (Table 1) results in the formations of two planar five-membered rings D (N1/N2/C4/C5/H5A) and E (N1/C7/C10/C11/H11A), in which they are oriented with respect to the adjacent rings at dihedral angles of A/D = 4.87 (3) and C/E = 0.86 (3)°. So, rings C and E are coplanar, while A and D are nearly coplanar.

In the crystal structure, intermolecular N-H···O and C-H···F hydrogen bonds (Table 2) link the molecules (Fig. 2) by forming the R₂²(8) and R₂²(18) ring motifs (Bernstein et al., 1995), in which they may be effective in the stabilization of the structure. The weak C—H···π interactions (Table 1) may further stabilize the structure.

Related literature top

For general background, see: Prakash et al. (2008); Nonaka (2003); Mabuchi & Ohtsuka (1999). For a related structure, see: Liu et al. (2008). For bond-length data, see: Allen et al. (1987). For ring motifs, see: Bernstein et al. (1995). Cg1 and Cg2 are centroids of the C1–C6 andC10–C15 rings, respectively.

Experimental top

The title compound was prepared according to the literature method (Liu et al., 2008). Crystals suitable for X-ray analysis were obtained by dissolving the title compound (1.5 g) in ethyl acetate (25 ml) and evaporating the solvent slowly at room temperature for about 10 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

1-(4-Fluorophenyl)-5-(4-methoxyphenyl)pyrazolidin-3-one top

Crystal data top

C₁₆H₁₅FN₂O₂	F(000) = 600
M_r = 286.30	D_x = 1.303 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.455 (2) Å	θ = 10–13°
b = 7.1590 (14) Å	µ = 0.10 mm⁻¹
c = 18.136 (4) Å	T = 294 K
β = 101.05 (3)°	Needle, colorless
V = 1459.7 (5) Å³	0.4 × 0.4 × 0.3 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1869 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 26.0°, θ_min = 1.8°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
T_min = 0.969, T_max = 0.991	l = −21→21
2991 measured reflections	3 standard reflections every 120 min
2844 independent reflections	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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.164	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
2844 reflections	Δρ_max = 0.18 e Å⁻³
191 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.038 (5)

Crystal data top

C₁₆H₁₅FN₂O₂	V = 1459.7 (5) Å³
M_r = 286.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.455 (2) Å	µ = 0.10 mm⁻¹
b = 7.1590 (14) Å	T = 294 K
c = 18.136 (4) Å	0.4 × 0.4 × 0.3 mm
β = 101.05 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1869 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.023
T_min = 0.969, T_max = 0.991	3 standard reflections every 120 min
2991 measured reflections	intensity decay: none
2844 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.01	Δρ_max = 0.18 e Å⁻³
2844 reflections	Δρ_min = −0.18 e Å⁻³
191 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
O1	0.48784 (13)	0.2552 (2)	0.03274 (8)	0.0523 (4)
O2	0.38835 (15)	−0.1685 (2)	−0.36578 (8)	0.0597 (5)
N1	0.26509 (14)	0.3997 (2)	−0.11625 (9)	0.0405 (4)
N2	0.37005 (14)	0.4183 (2)	−0.06107 (10)	0.0468 (5)
H2A	0.4116	0.5192	−0.0556	0.056*
F	−0.11183 (16)	0.8402 (3)	−0.07221 (14)	0.1260 (8)
C1	−0.0185 (2)	0.7276 (4)	−0.08105 (18)	0.0724 (8)
C2	−0.0298 (2)	0.6229 (4)	−0.14437 (16)	0.0694 (8)
H2B	−0.0996	0.6247	−0.1803	0.083*
C3	0.0654 (2)	0.5135 (3)	−0.15406 (13)	0.0541 (6)
H3A	0.0603	0.4424	−0.1975	0.065*
C4	0.16815 (17)	0.5086 (2)	−0.09998 (11)	0.0393 (5)
C5	0.1755 (2)	0.6150 (3)	−0.03597 (12)	0.0525 (6)
H5A	0.2443	0.6122	0.0009	0.063*
C6	0.0806 (2)	0.7261 (4)	−0.02653 (17)	0.0723 (8)
H6A	0.0848	0.7985	0.0165	0.087*
C7	0.24222 (18)	0.1930 (3)	−0.12010 (11)	0.0393 (5)
H7A	0.1569	0.1709	−0.1237	0.047*
C8	0.30920 (19)	0.1193 (3)	−0.04418 (10)	0.0436 (5)
H8A	0.2559	0.1040	−0.0090	0.052*
H8B	0.3472	0.0006	−0.0501	0.052*
C9	0.39987 (18)	0.2682 (3)	−0.01826 (11)	0.0416 (5)
C10	0.28206 (17)	0.1019 (3)	−0.18638 (10)	0.0391 (5)
C11	0.33591 (18)	0.1959 (3)	−0.23771 (11)	0.0443 (5)
H11A	0.3490	0.3238	−0.2323	0.053*
C12	0.3703 (2)	0.1032 (3)	−0.29659 (11)	0.0486 (5)
H12A	0.4069	0.1687	−0.3302	0.058*
C13	0.35087 (19)	−0.0874 (3)	−0.30603 (10)	0.0455 (5)
C14	0.2963 (2)	−0.1830 (3)	−0.25569 (13)	0.0592 (7)
H14A	0.2825	−0.3107	−0.2613	0.071*
C15	0.2625 (2)	−0.0876 (3)	−0.19703 (12)	0.0560 (6)
H15A	0.2254	−0.1529	−0.1636	0.067*
C16	0.3801 (2)	−0.3669 (4)	−0.37188 (14)	0.0655 (7)
H16A	0.4084	−0.4069	−0.4158	0.098*
H16B	0.2987	−0.4044	−0.3758	0.098*
H16C	0.4276	−0.4230	−0.3281	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0529 (9)	0.0421 (9)	0.0565 (9)	0.0060 (7)	−0.0034 (7)	0.0017 (7)
O2	0.0751 (11)	0.0584 (11)	0.0486 (9)	−0.0018 (8)	0.0194 (8)	−0.0099 (7)
N1	0.0387 (9)	0.0295 (9)	0.0521 (10)	0.0020 (7)	0.0053 (7)	−0.0001 (7)
N2	0.0361 (9)	0.0319 (9)	0.0678 (11)	−0.0014 (7)	−0.0017 (8)	0.0030 (8)
F	0.0732 (12)	0.1078 (16)	0.200 (2)	0.0392 (11)	0.0325 (13)	−0.0413 (15)
C1	0.0470 (14)	0.0575 (16)	0.114 (2)	0.0138 (12)	0.0199 (15)	−0.0134 (15)
C2	0.0464 (14)	0.0637 (17)	0.0911 (19)	0.0095 (12)	−0.0040 (13)	−0.0011 (15)
C3	0.0482 (13)	0.0478 (13)	0.0622 (14)	0.0055 (10)	−0.0001 (10)	−0.0054 (11)
C4	0.0425 (11)	0.0267 (10)	0.0486 (11)	0.0025 (8)	0.0082 (9)	0.0043 (8)
C5	0.0536 (13)	0.0472 (13)	0.0551 (13)	0.0021 (10)	0.0069 (10)	−0.0084 (10)
C6	0.0711 (18)	0.0606 (17)	0.0880 (19)	0.0055 (13)	0.0226 (15)	−0.0289 (14)
C7	0.0399 (10)	0.0281 (10)	0.0501 (11)	−0.0005 (8)	0.0090 (9)	0.0009 (8)
C8	0.0552 (13)	0.0344 (11)	0.0425 (11)	−0.0020 (9)	0.0131 (9)	0.0010 (9)
C9	0.0455 (11)	0.0328 (11)	0.0476 (11)	0.0064 (9)	0.0122 (9)	−0.0014 (9)
C10	0.0441 (11)	0.0322 (10)	0.0395 (10)	0.0001 (8)	0.0044 (8)	0.0022 (8)
C11	0.0478 (12)	0.0341 (10)	0.0495 (12)	−0.0044 (9)	0.0060 (9)	0.0027 (9)
C12	0.0550 (13)	0.0484 (13)	0.0434 (11)	−0.0081 (10)	0.0120 (10)	0.0032 (9)
C13	0.0501 (12)	0.0479 (13)	0.0365 (10)	0.0015 (10)	0.0032 (9)	−0.0026 (9)
C14	0.0896 (19)	0.0362 (12)	0.0557 (13)	−0.0053 (12)	0.0238 (13)	−0.0048 (10)
C15	0.0857 (17)	0.0367 (12)	0.0518 (12)	−0.0080 (11)	0.0287 (12)	0.0011 (9)
C16	0.0717 (16)	0.0648 (16)	0.0614 (14)	−0.0109 (13)	0.0162 (12)	−0.0278 (13)

Geometric parameters (Å, º) top

O1—C9	1.234 (2)	C7—C8	1.536 (3)
O2—C13	1.369 (2)	C7—C10	1.513 (3)
O2—C16	1.427 (3)	C7—H7A	0.9800
N1—N2	1.415 (2)	C8—H8A	0.9700
N1—C4	1.433 (2)	C8—H8B	0.9700
N1—C7	1.502 (2)	C9—C8	1.500 (3)
N2—C9	1.331 (2)	C10—C15	1.382 (3)
N2—H2A	0.8600	C11—C10	1.386 (3)
F—C1	1.372 (3)	C11—C12	1.378 (3)
C2—C1	1.357 (4)	C11—H11A	0.9300
C2—H2B	0.9300	C12—C13	1.388 (3)
C3—C2	1.380 (3)	C12—H12A	0.9300
C3—H3A	0.9300	C13—C14	1.382 (3)
C4—C3	1.381 (3)	C14—C15	1.381 (3)
C4—C5	1.378 (3)	C14—H14A	0.9300
C5—C6	1.384 (3)	C15—H15A	0.9300
C5—H5A	0.9300	C16—H16A	0.9600
C6—C1	1.356 (4)	C16—H16B	0.9600
C6—H6A	0.9300	C16—H16C	0.9600

C13—O2—C16	117.22 (18)	C7—C8—H8B	111.1
N2—N1—C4	112.97 (15)	C9—C8—C7	103.53 (16)
N2—N1—C7	104.02 (14)	C9—C8—H8A	111.1
C4—N1—C7	114.23 (15)	C9—C8—H8B	111.1
N1—N2—H2A	122.4	H8A—C8—H8B	109.0
C9—N2—N1	115.13 (16)	O1—C9—N2	125.42 (19)
C9—N2—H2A	122.4	O1—C9—C8	126.75 (18)
C2—C1—F	118.3 (3)	N2—C9—C8	107.82 (17)
C6—C1—F	118.8 (3)	C15—C10—C11	117.64 (19)
C6—C1—C2	122.9 (2)	C15—C10—C7	117.95 (18)
C1—C2—C3	118.2 (2)	C11—C10—C7	124.40 (18)
C1—C2—H2B	120.9	C10—C11—H11A	119.4
C3—C2—H2B	120.9	C12—C11—C10	121.1 (2)
C2—C3—C4	120.7 (2)	C12—C11—H11A	119.4
C2—C3—H3A	119.7	C11—C12—C13	120.42 (19)
C4—C3—H3A	119.7	C11—C12—H12A	119.8
C3—C4—N1	117.15 (18)	C13—C12—H12A	119.8
C5—C4—N1	123.33 (18)	O2—C13—C14	124.3 (2)
C5—C4—C3	119.40 (19)	O2—C13—C12	116.56 (19)
C4—C5—C6	120.0 (2)	C14—C13—C12	119.17 (19)
C4—C5—H5A	120.0	C15—C14—C13	119.6 (2)
C6—C5—H5A	120.0	C15—C14—H14A	120.2
C1—C6—C5	118.9 (2)	C13—C14—H14A	120.2
C1—C6—H6A	120.6	C10—C15—H15A	119.0
C5—C6—H6A	120.6	C14—C15—C10	122.1 (2)
N1—C7—C8	104.13 (15)	C14—C15—H15A	119.0
N1—C7—C10	112.66 (16)	O2—C16—H16A	109.5
N1—C7—H7A	109.0	O2—C16—H16B	109.5
C8—C7—H7A	109.0	O2—C16—H16C	109.5
C10—C7—C8	112.90 (16)	H16A—C16—H16B	109.5
C10—C7—H7A	109.0	H16A—C16—H16C	109.5
C7—C8—H8A	111.1	H16B—C16—H16C	109.5

C4—N1—N2—C9	109.31 (19)	C4—C5—C6—C1	0.1 (4)
C7—N1—N2—C9	−15.1 (2)	C5—C6—C1—C2	0.8 (5)
N2—N1—C4—C3	174.02 (17)	C5—C6—C1—F	−178.9 (3)
N2—N1—C4—C5	−2.1 (3)	N1—C7—C8—C9	−21.70 (19)
C7—N1—C4—C3	−67.3 (2)	C10—C7—C8—C9	100.83 (19)
C7—N1—C4—C5	116.5 (2)	N1—C7—C10—C11	1.1 (3)
N2—N1—C7—C8	22.13 (18)	N1—C7—C10—C15	−178.22 (19)
N2—N1—C7—C10	−100.56 (17)	C8—C7—C10—C11	−116.5 (2)
C4—N1—C7—C8	−101.47 (18)	C8—C7—C10—C15	64.2 (2)
C4—N1—C7—C10	135.84 (17)	O1—C9—C8—C7	−165.5 (2)
N1—N2—C9—O1	179.81 (18)	N2—C9—C8—C7	13.5 (2)
N1—N2—C9—C8	0.8 (2)	C7—C10—C15—C14	−179.7 (2)
C16—O2—C13—C12	173.8 (2)	C11—C10—C15—C14	0.9 (3)
C16—O2—C13—C14	−6.0 (3)	C12—C11—C10—C7	179.69 (19)
C3—C2—C1—C6	−1.5 (4)	C12—C11—C10—C15	−1.0 (3)
C3—C2—C1—F	178.3 (3)	C10—C11—C12—C13	0.5 (3)
C4—C3—C2—C1	1.2 (4)	C11—C12—C13—O2	−179.71 (19)
N1—C4—C3—C2	−176.6 (2)	C11—C12—C13—C14	0.1 (3)
C5—C4—C3—C2	−0.4 (3)	O2—C13—C14—C15	179.7 (2)
N1—C4—C5—C6	175.7 (2)	C12—C13—C14—C15	−0.1 (4)
C3—C4—C5—C6	−0.3 (3)	C13—C14—C15—C10	−0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	1.98	2.838 (2)	175
C5—H5A···N2	0.93	2.43	2.747 (3)	100
C8—H8A···Fⁱⁱ	0.97	2.45	3.388 (3)	164
C11—H11A···N1	0.93	2.53	2.885 (3)	103
C2—H2B···Cg2ⁱⁱⁱ	0.93	2.71	3.589 (3)	157
C15—H15A···Cg1^iv	0.93	2.89	3.801 (3)	167

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅FN₂O₂
M_r	286.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	11.455 (2), 7.1590 (14), 18.136 (4)
β (°)	101.05 (3)
V (Å³)	1459.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.4 × 0.4 × 0.3

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.969, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	2991, 2844, 1869
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.164, 1.01
No. of reflections	2844
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	1.98	2.838 (2)	175
C5—H5A···N2	0.93	2.43	2.747 (3)	100
C8—H8A···Fⁱⁱ	0.97	2.45	3.388 (3)	164
C11—H11A···N1	0.93	2.53	2.885 (3)	103
C2—H2B···Cg2ⁱⁱⁱ	0.93	2.71	3.589 (3)	157
C15—H15A···Cg1^iv	0.93	2.89	3.801 (3)	167

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

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

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