1-[3-(Anthracen-9-yl)-5-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone.

In the title compound, C(24)H(19)N(3)O, the pyrazoline ring adopts an envelope conformation with the C atom linking to the pyridine ring as the flap. The mean plane of the pyrazoline ring makes dihedral angles of 85.54 (4) and 81.66 (3)° with the pyridine ring and the anthracene ring system, respectively. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds. In addition, weak π-π inter-actions [centroid-centroid distances = 3.695 (3)-3.850 (7) Å] are observed.

Related literature

For applications of pyrazoline derivitives, see: Amir et al. (2008 ▶); Stell (2005 ▶). For the synthesis of the title compound, see: Lévai & Jekó (2006 ▶). For a related structure, see: Liu et al. (2008 ▶).

Experimental

Crystal data

C24H19N3O

M = 365.42

Monoclinic,

a = 10.1768 (8) Å

b = 23.6035 (18) Å

c = 7.9994 (7) Å

β = 109.134 (3)°

V = 1815.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.28 × 0.26 × 0.24 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004 ▶) T min = 0.977, T max = 0.980

10313 measured reflections

3544 independent reflections

3081 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.102

S = 1.02

3544 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201505X/hb6687sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201505X/hb6687Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201505X/hb6687Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H19N3O	F(000) = 768
Mr = 365.42	Dx = 1.337 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71070 Å
a = 10.1768 (8) Å	Cell parameters from 5004 reflections
b = 23.6035 (18) Å	θ = 2.3–27.9°
c = 7.9994 (7) Å	µ = 0.08 mm−1
β = 109.134 (3)°	T = 293 K
V = 1815.4 (3) Å3	Prism, colorless
Z = 4	0.28 × 0.26 × 0.24 mm

Rigaku Saturn diffractometer	3544 independent reflections
Radiation source: Rotating anode	3081 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 7.31 pixels mm-1	θmax = 26.0°, θmin = 2.3°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004)	k = −24→28
Tmin = 0.977, Tmax = 0.980	l = −7→9
10313 measured reflections

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.4522P] where P = (Fo2 + 2Fc2)/3
3544 reflections	(Δ/σ)max = 0.001
254 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.56753 (10)	1.02852 (4)	0.79960 (12)	0.0256 (2)
N1	0.71048 (10)	0.91596 (4)	0.62713 (13)	0.0169 (2)
N2	0.67267 (10)	0.97037 (4)	0.66237 (13)	0.0168 (2)
N3	0.96041 (11)	1.02330 (5)	0.76512 (14)	0.0215 (2)
C1	0.96119 (13)	0.85347 (5)	0.51788 (16)	0.0181 (3)
C2	1.05711 (13)	0.88660 (5)	0.65379 (17)	0.0209 (3)
H2	1.0268	0.9196	0.6931	0.025*
C3	1.19243 (14)	0.87026 (6)	0.72619 (18)	0.0254 (3)
H3	1.2528	0.8918	0.8163	0.030*
C4	1.24244 (14)	0.82064 (6)	0.66544 (19)	0.0276 (3)
H4	1.3355	0.8104	0.7139	0.033*
C5	1.15428 (14)	0.78817 (6)	0.53671 (18)	0.0256 (3)
H5	1.1883	0.7561	0.4971	0.031*
C6	1.01021 (13)	0.80235 (5)	0.46098 (16)	0.0211 (3)
C7	0.91593 (14)	0.76766 (5)	0.33701 (17)	0.0233 (3)
H7	0.9479	0.7345	0.3007	0.028*
C8	0.77543 (14)	0.78134 (5)	0.26632 (16)	0.0212 (3)
C9	0.67714 (15)	0.74428 (6)	0.14834 (18)	0.0271 (3)
H9	0.7073	0.7099	0.1173	0.033*
C10	0.54048 (15)	0.75826 (6)	0.08056 (18)	0.0286 (3)
H10	0.4782	0.7336	0.0035	0.034*
C11	0.49232 (14)	0.81050 (6)	0.12697 (17)	0.0245 (3)
H11	0.3987	0.8200	0.0787	0.029*
C12	0.58172 (13)	0.84699 (5)	0.24163 (16)	0.0201 (3)
H12	0.5483	0.8809	0.2711	0.024*
C13	0.72615 (13)	0.83364 (5)	0.31691 (16)	0.0180 (3)
C14	0.82019 (13)	0.86851 (5)	0.44328 (15)	0.0169 (3)
C15	0.76793 (12)	0.92032 (5)	0.50670 (15)	0.0158 (3)
C16	0.77237 (12)	0.97959 (5)	0.43933 (16)	0.0168 (3)
H16A	0.7102	0.9837	0.3187	0.020*
H16B	0.8659	0.9900	0.4446	0.020*
C17	0.72303 (12)	1.01539 (5)	0.56842 (16)	0.0161 (3)
H17	0.6460	1.0402	0.5030	0.019*
C18	0.83723 (12)	1.04959 (5)	0.69927 (15)	0.0166 (3)
C19	0.81301 (14)	1.10378 (5)	0.74894 (17)	0.0219 (3)
H19	0.7262	1.1206	0.7005	0.026*
C20	0.92081 (15)	1.13239 (6)	0.87233 (18)	0.0268 (3)
H20	0.9077	1.1690	0.9069	0.032*
C21	1.04791 (14)	1.10572 (6)	0.94313 (17)	0.0262 (3)
H21	1.1217	1.1237	1.0271	0.031*
C22	1.06228 (14)	1.05162 (6)	0.88576 (17)	0.0250 (3)
H22	1.1479	1.0337	0.9337	0.030*
C23	0.59907 (12)	0.97977 (5)	0.77386 (16)	0.0178 (3)
C24	0.55832 (13)	0.92892 (6)	0.85831 (17)	0.0231 (3)
H24A	0.5094	0.9410	0.9363	0.035*
H24B	0.6403	0.9084	0.9245	0.035*
H24C	0.4992	0.9048	0.7681	0.035*

	U11	U22	U33	U12	U13	U23
O1	0.0268 (5)	0.0234 (5)	0.0315 (5)	0.0046 (4)	0.0160 (4)	−0.0018 (4)
N1	0.0169 (5)	0.0145 (5)	0.0197 (5)	−0.0002 (4)	0.0066 (4)	−0.0027 (4)
N2	0.0174 (5)	0.0137 (5)	0.0208 (5)	−0.0006 (4)	0.0086 (4)	−0.0014 (4)
N3	0.0190 (5)	0.0223 (6)	0.0210 (5)	−0.0005 (4)	0.0037 (4)	−0.0005 (4)
C1	0.0212 (6)	0.0173 (6)	0.0190 (6)	0.0007 (5)	0.0108 (5)	0.0037 (5)
C2	0.0223 (6)	0.0196 (7)	0.0229 (6)	0.0005 (5)	0.0101 (5)	0.0018 (5)
C3	0.0217 (7)	0.0298 (8)	0.0242 (7)	−0.0001 (5)	0.0068 (5)	0.0035 (6)
C4	0.0209 (7)	0.0313 (8)	0.0320 (7)	0.0074 (6)	0.0107 (6)	0.0086 (6)
C5	0.0282 (7)	0.0224 (7)	0.0309 (7)	0.0087 (6)	0.0160 (6)	0.0061 (6)
C6	0.0251 (7)	0.0194 (7)	0.0229 (6)	0.0042 (5)	0.0134 (5)	0.0045 (5)
C7	0.0340 (8)	0.0168 (7)	0.0246 (7)	0.0045 (5)	0.0173 (6)	−0.0004 (5)
C8	0.0300 (7)	0.0186 (7)	0.0185 (6)	−0.0006 (5)	0.0130 (5)	−0.0001 (5)
C9	0.0391 (8)	0.0210 (7)	0.0247 (7)	−0.0014 (6)	0.0153 (6)	−0.0065 (5)
C10	0.0371 (8)	0.0271 (8)	0.0217 (7)	−0.0097 (6)	0.0097 (6)	−0.0082 (6)
C11	0.0256 (7)	0.0263 (7)	0.0207 (6)	−0.0040 (5)	0.0062 (5)	−0.0011 (5)
C12	0.0254 (7)	0.0174 (6)	0.0190 (6)	−0.0002 (5)	0.0095 (5)	0.0005 (5)
C13	0.0244 (6)	0.0157 (6)	0.0169 (6)	−0.0012 (5)	0.0106 (5)	0.0009 (5)
C14	0.0213 (6)	0.0156 (6)	0.0166 (6)	0.0002 (5)	0.0100 (5)	0.0019 (5)
C15	0.0130 (5)	0.0176 (6)	0.0158 (6)	−0.0014 (4)	0.0034 (4)	−0.0014 (5)
C16	0.0171 (6)	0.0168 (6)	0.0171 (6)	−0.0011 (5)	0.0062 (5)	−0.0004 (5)
C17	0.0171 (6)	0.0139 (6)	0.0177 (6)	0.0008 (5)	0.0064 (5)	0.0015 (5)
C18	0.0187 (6)	0.0174 (6)	0.0152 (6)	−0.0019 (5)	0.0078 (5)	0.0019 (5)
C19	0.0220 (6)	0.0212 (7)	0.0238 (6)	0.0001 (5)	0.0095 (5)	−0.0011 (5)
C20	0.0333 (8)	0.0222 (7)	0.0274 (7)	−0.0057 (6)	0.0132 (6)	−0.0081 (6)
C21	0.0259 (7)	0.0324 (8)	0.0200 (6)	−0.0104 (6)	0.0071 (5)	−0.0053 (6)
C22	0.0189 (7)	0.0320 (8)	0.0213 (6)	−0.0017 (5)	0.0026 (5)	0.0000 (6)
C23	0.0129 (6)	0.0228 (7)	0.0174 (6)	−0.0004 (5)	0.0045 (5)	−0.0026 (5)
C24	0.0215 (6)	0.0274 (7)	0.0237 (6)	−0.0015 (5)	0.0119 (5)	−0.0004 (5)

O1—C23	1.2298 (15)	C10—H10	0.9300
N1—C15	1.2844 (15)	C11—C12	1.3651 (18)
N1—N2	1.3957 (13)	C11—H11	0.9300
N2—C23	1.3578 (15)	C12—C13	1.4290 (18)
N2—C17	1.4862 (15)	C12—H12	0.9300
N3—C22	1.3406 (17)	C13—C14	1.4075 (17)
N3—C18	1.3420 (16)	C14—C15	1.4874 (16)
C1—C14	1.4071 (17)	C15—C16	1.5052 (17)
C1—C2	1.4321 (18)	C16—C17	1.5402 (16)
C1—C6	1.4355 (18)	C16—H16A	0.9700
C2—C3	1.3630 (18)	C16—H16B	0.9700
C2—H2	0.9300	C17—C18	1.5168 (17)
C3—C4	1.4244 (19)	C17—H17	0.9800
C3—H3	0.9300	C18—C19	1.3852 (17)
C4—C5	1.359 (2)	C19—C20	1.3871 (19)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.4305 (18)	C20—C21	1.382 (2)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.3966 (19)	C21—C22	1.3806 (19)
C7—C8	1.3923 (19)	C21—H21	0.9300
C7—H7	0.9300	C22—H22	0.9300
C8—C9	1.4274 (19)	C23—C24	1.5009 (17)
C8—C13	1.4396 (17)	C24—H24A	0.9600
C9—C10	1.358 (2)	C24—H24B	0.9600
C9—H9	0.9300	C24—H24C	0.9600
C10—C11	1.420 (2)
C15—N1—N2	107.53 (10)	C12—C13—C8	118.40 (11)
C23—N2—N1	122.08 (10)	C1—C14—C13	121.05 (11)
C23—N2—C17	124.83 (10)	C1—C14—C15	119.46 (11)
N1—N2—C17	113.08 (9)	C13—C14—C15	119.39 (11)
C22—N3—C18	117.04 (11)	N1—C15—C14	119.44 (11)
C14—C1—C2	122.05 (11)	N1—C15—C16	114.67 (10)
C14—C1—C6	119.33 (11)	C14—C15—C16	125.87 (10)
C2—C1—C6	118.58 (11)	C15—C16—C17	102.42 (9)
C3—C2—C1	120.69 (12)	C15—C16—H16A	111.3
C3—C2—H2	119.7	C17—C16—H16A	111.3
C1—C2—H2	119.7	C15—C16—H16B	111.3
C2—C3—C4	120.79 (13)	C17—C16—H16B	111.3
C2—C3—H3	119.6	H16A—C16—H16B	109.2
C4—C3—H3	119.6	N2—C17—C18	110.17 (9)
C5—C4—C3	120.07 (12)	N2—C17—C16	100.90 (9)
C5—C4—H4	120.0	C18—C17—C16	114.22 (10)
C3—C4—H4	120.0	N2—C17—H17	110.4
C4—C5—C6	121.29 (12)	C18—C17—H17	110.4
C4—C5—H5	119.4	C16—C17—H17	110.4
C6—C5—H5	119.4	N3—C18—C19	123.05 (11)
C7—C6—C5	122.26 (12)	N3—C18—C17	115.51 (10)
C7—C6—C1	119.24 (12)	C19—C18—C17	121.42 (11)
C5—C6—C1	118.48 (12)	C18—C19—C20	118.69 (12)
C8—C7—C6	121.84 (12)	C18—C19—H19	120.7
C8—C7—H7	119.1	C20—C19—H19	120.7
C6—C7—H7	119.1	C21—C20—C19	119.04 (13)
C7—C8—C9	122.02 (12)	C21—C20—H20	120.5
C7—C8—C13	119.38 (12)	C19—C20—H20	120.5
C9—C8—C13	118.57 (12)	C22—C21—C20	118.17 (12)
C10—C9—C8	121.28 (12)	C22—C21—H21	120.9
C10—C9—H9	119.4	C20—C21—H21	120.9
C8—C9—H9	119.4	N3—C22—C21	124.00 (12)
C9—C10—C11	120.18 (12)	N3—C22—H22	118.0
C9—C10—H10	119.9	C21—C22—H22	118.0
C11—C10—H10	119.9	O1—C23—N2	119.56 (11)
C12—C11—C10	120.81 (13)	O1—C23—C24	123.16 (11)
C12—C11—H11	119.6	N2—C23—C24	117.27 (11)
C10—C11—H11	119.6	C23—C24—H24A	109.5
C11—C12—C13	120.73 (12)	C23—C24—H24B	109.5
C11—C12—H12	119.6	H24A—C24—H24B	109.5
C13—C12—H12	119.6	C23—C24—H24C	109.5
C14—C13—C12	122.48 (11)	H24A—C24—H24C	109.5
C14—C13—C8	119.07 (11)	H24B—C24—H24C	109.5
C15—N1—N2—C23	174.55 (11)	C8—C13—C14—C1	1.11 (17)
C15—N1—N2—C17	−6.35 (13)	C12—C13—C14—C15	2.16 (17)
C14—C1—C2—C3	178.56 (12)	C8—C13—C14—C15	−175.24 (10)
C6—C1—C2—C3	0.70 (18)	N2—N1—C15—C14	179.49 (10)
C1—C2—C3—C4	1.56 (19)	N2—N1—C15—C16	−1.87 (13)
C2—C3—C4—C5	−1.6 (2)	C1—C14—C15—N1	−95.42 (14)
C3—C4—C5—C6	−0.7 (2)	C13—C14—C15—N1	80.99 (14)
C4—C5—C6—C7	−175.71 (12)	C1—C14—C15—C16	86.11 (15)
C4—C5—C6—C1	2.95 (19)	C13—C14—C15—C16	−97.48 (14)
C14—C1—C6—C7	−2.10 (18)	N1—C15—C16—C17	8.65 (13)
C2—C1—C6—C7	175.81 (11)	C14—C15—C16—C17	−172.82 (11)
C14—C1—C6—C5	179.20 (11)	C23—N2—C17—C18	69.14 (14)
C2—C1—C6—C5	−2.89 (17)	N1—N2—C17—C18	−109.93 (11)
C5—C6—C7—C8	178.87 (12)	C23—N2—C17—C16	−169.81 (11)
C1—C6—C7—C8	0.22 (19)	N1—N2—C17—C16	11.12 (12)
C6—C7—C8—C9	−175.89 (12)	C15—C16—C17—N2	−10.80 (11)
C6—C7—C8—C13	2.32 (19)	C15—C16—C17—C18	107.34 (11)
C7—C8—C9—C10	−179.99 (12)	C22—N3—C18—C19	0.75 (18)
C13—C8—C9—C10	1.78 (19)	C22—N3—C18—C17	−177.77 (10)
C8—C9—C10—C11	−0.3 (2)	N2—C17—C18—N3	73.20 (13)
C9—C10—C11—C12	−0.9 (2)	C16—C17—C18—N3	−39.52 (14)
C10—C11—C12—C13	0.39 (19)	N2—C17—C18—C19	−105.35 (12)
C11—C12—C13—C14	−176.25 (11)	C16—C17—C18—C19	141.94 (11)
C11—C12—C13—C8	1.16 (18)	N3—C18—C19—C20	0.06 (19)
C7—C8—C13—C14	−2.97 (17)	C17—C18—C19—C20	178.49 (11)
C9—C8—C13—C14	175.30 (11)	C18—C19—C20—C21	−0.82 (19)
C7—C8—C13—C12	179.53 (11)	C19—C20—C21—C22	0.74 (19)
C9—C8—C13—C12	−2.20 (17)	C18—N3—C22—C21	−0.84 (19)
C2—C1—C14—C13	−176.43 (11)	C20—C21—C22—N3	0.1 (2)
C6—C1—C14—C13	1.41 (18)	N1—N2—C23—O1	−179.52 (10)
C2—C1—C14—C15	−0.08 (18)	C17—N2—C23—O1	1.48 (18)
C6—C1—C14—C15	177.76 (10)	N1—N2—C23—C24	−0.39 (16)
C12—C13—C14—C1	178.50 (11)	C17—N2—C23—C24	−179.38 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1i	0.93	2.42	3.2745 (16)	153
C24—H24A···O1ii	0.96	2.58	3.5265 (16)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.93	2.42	3.2745 (16)	153
C24—H24A⋯O1ii	0.96	2.58	3.5265 (16)	167

Symmetry codes: (i) ; (ii) .