1-[3-(2-Naphth-yl)-5-(3,4,5-trimethoxy-phen-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone.

In the title compound, C(24)H(24)N(2)O(4), the pendant benzene and naphthalene ring systems make dihedral angles of 87.9 (3) and 19.2 (3)°, respectively, with the central pyrazoline ring. In the crystal structure, weak C-H⋯O inter-actions help to establish the packing.

Related literature

For a related structure, see: Lu et al. (2006 ▶).

Experimental

Crystal data

C24H24N2O4

M = 404.45

Monoclinic,

a = 12.611 (3) Å

b = 15.177 (3) Å

c = 10.580 (2) Å

β = 92.03 (3)°

V = 2023.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 113 (2) K

0.14 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T min = 0.987, T max = 0.991

24346 measured reflections

4655 independent reflections

3976 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.129

S = 1.07

4655 reflections

275 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku, 2008 ▶); 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801979X/hb2755sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801979X/hb2755Isup2.hkl

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

C24H24N2O4	F000 = 856
Mr = 404.45	Dx = 1.328 Mg m−3
Monoclinic, P21/c	Melting point = 415–416 K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 12.611 (3) Å	Cell parameters from 5898 reflections
b = 15.177 (3) Å	θ = 1.9–27.5º
c = 10.580 (2) Å	µ = 0.09 mm−1
β = 92.03 (3)º	T = 113 (2) K
V = 2023.6 (7) Å3	Block, colourless
Z = 4	0.14 × 0.12 × 0.10 mm

Rigaku Saturn diffractometer	4655 independent reflections
Radiation source: rotating anode	3976 reflections with I > 2σ(I)
Monochromator: confocal	Rint = 0.040
T = 113(2) K	θmax = 27.5º
ω scans	θmin = 1.6º
Absorption correction: multi-scan(CrystalClear; Rigaku, 2008)	h = −16→16
Tmin = 0.987, Tmax = 0.991	k = −19→19
24346 measured reflections	l = −13→13

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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.129	w = 1/[σ2(Fo2) + (0.0756P)2 + 0.2039P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
4655 reflections	Δρmax = 0.22 e Å−3
275 parameters	Δρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.55819 (8)	0.34748 (6)	0.49413 (9)	0.0273 (2)
O2	0.26913 (7)	0.14553 (6)	0.77917 (8)	0.0227 (2)
O3	0.20369 (7)	0.09108 (6)	0.55062 (9)	0.0220 (2)
O4	0.33628 (7)	0.06865 (6)	0.36480 (8)	0.0234 (2)
N1	0.72197 (8)	0.30131 (7)	0.76057 (10)	0.0197 (2)
N2	0.64355 (8)	0.29005 (7)	0.66497 (10)	0.0197 (2)
C1	0.85205 (10)	0.13495 (9)	0.95665 (12)	0.0216 (3)
H1	0.8091	0.0874	0.9338	0.026*
C2	0.93150 (10)	0.12422 (9)	1.05376 (12)	0.0231 (3)
C3	0.94735 (11)	0.04348 (10)	1.11946 (13)	0.0283 (3)
H3	0.9034	−0.0043	1.1005	0.034*
C4	1.02660 (12)	0.03530 (11)	1.21027 (14)	0.0342 (4)
H4	1.0357	−0.0178	1.2532	0.041*
C5	1.09444 (12)	0.10648 (12)	1.23931 (14)	0.0377 (4)
H5	1.1488	0.0999	1.3003	0.045*
C6	1.08098 (11)	0.18525 (12)	1.17846 (14)	0.0351 (4)
H6	1.1262	0.2320	1.1987	0.042*
C7	0.99889 (10)	0.19670 (10)	1.08487 (13)	0.0261 (3)
C8	0.98307 (11)	0.27731 (10)	1.01867 (14)	0.0301 (3)
H8	1.0270	0.3250	1.0380	0.036*
C9	0.90514 (10)	0.28610 (9)	0.92784 (13)	0.0253 (3)
H9	0.8960	0.3397	0.8862	0.030*
C10	0.83730 (10)	0.21415 (9)	0.89572 (12)	0.0197 (3)
C11	0.75408 (9)	0.22457 (8)	0.79621 (12)	0.0184 (3)
C12	0.69637 (10)	0.14964 (9)	0.73107 (12)	0.0214 (3)
H12A	0.6501	0.1195	0.7883	0.026*
H12B	0.7457	0.1075	0.6971	0.026*
C13	0.63207 (10)	0.19680 (8)	0.62438 (12)	0.0192 (3)
H13	0.6678	0.1887	0.5445	0.023*
C14	0.51784 (10)	0.16670 (8)	0.60773 (12)	0.0184 (3)
C15	0.48490 (10)	0.12988 (8)	0.49248 (12)	0.0195 (3)
H15	0.5323	0.1240	0.4276	0.023*
C16	0.37999 (10)	0.10182 (8)	0.47523 (11)	0.0184 (3)
C17	0.30944 (10)	0.11043 (8)	0.57241 (12)	0.0184 (3)
C18	0.34422 (10)	0.14469 (8)	0.68948 (12)	0.0180 (3)
C19	0.44879 (10)	0.17348 (8)	0.70697 (12)	0.0191 (3)
H19	0.4721	0.1970	0.7842	0.023*
C20	0.29410 (12)	0.19068 (11)	0.89501 (13)	0.0322 (3)
H20A	0.3559	0.1646	0.9353	0.048*
H20B	0.2353	0.1862	0.9499	0.048*
H20C	0.3079	0.2516	0.8776	0.048*
C21	0.17898 (11)	−0.00027 (9)	0.56046 (13)	0.0262 (3)
H21A	0.2251	−0.0337	0.5084	0.039*
H21B	0.1066	−0.0099	0.5328	0.039*
H21C	0.1886	−0.0188	0.6469	0.039*
C22	0.40060 (12)	0.06731 (10)	0.25729 (13)	0.0293 (3)
H22A	0.4284	0.1252	0.2432	0.044*
H22B	0.3587	0.0490	0.1844	0.044*
H22C	0.4582	0.0267	0.2716	0.044*
C23	0.61160 (10)	0.35986 (9)	0.59197 (12)	0.0210 (3)
C24	0.64295 (11)	0.45014 (9)	0.63730 (13)	0.0256 (3)
H24A	0.7159	0.4608	0.6191	0.038*
H24B	0.6341	0.4540	0.7269	0.038*
H24C	0.5989	0.4934	0.5950	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0283 (5)	0.0300 (5)	0.0229 (5)	−0.0031 (4)	−0.0072 (4)	0.0026 (4)
O2	0.0205 (5)	0.0269 (5)	0.0209 (5)	−0.0017 (4)	0.0014 (4)	−0.0047 (4)
O3	0.0155 (4)	0.0227 (5)	0.0273 (5)	−0.0014 (3)	−0.0041 (4)	−0.0010 (4)
O4	0.0213 (5)	0.0314 (5)	0.0173 (4)	−0.0057 (4)	−0.0026 (4)	−0.0045 (4)
N1	0.0154 (5)	0.0242 (6)	0.0190 (5)	−0.0027 (4)	−0.0040 (4)	−0.0014 (4)
N2	0.0179 (5)	0.0210 (6)	0.0199 (5)	−0.0032 (4)	−0.0055 (4)	−0.0011 (4)
C1	0.0166 (6)	0.0257 (7)	0.0224 (6)	−0.0005 (5)	−0.0005 (5)	−0.0035 (5)
C2	0.0167 (6)	0.0330 (7)	0.0197 (6)	0.0049 (5)	0.0009 (5)	−0.0015 (5)
C3	0.0237 (7)	0.0368 (8)	0.0246 (7)	0.0074 (6)	0.0017 (5)	0.0026 (6)
C4	0.0285 (8)	0.0503 (10)	0.0239 (7)	0.0158 (7)	0.0025 (6)	0.0060 (7)
C5	0.0227 (7)	0.0669 (12)	0.0232 (7)	0.0119 (7)	−0.0052 (6)	0.0027 (7)
C6	0.0193 (7)	0.0589 (10)	0.0266 (7)	−0.0004 (7)	−0.0053 (6)	−0.0035 (7)
C7	0.0164 (6)	0.0400 (8)	0.0218 (6)	0.0012 (6)	−0.0015 (5)	−0.0030 (6)
C8	0.0211 (7)	0.0354 (8)	0.0333 (8)	−0.0074 (6)	−0.0049 (6)	−0.0050 (6)
C9	0.0214 (7)	0.0241 (7)	0.0299 (7)	−0.0021 (5)	−0.0034 (5)	−0.0005 (6)
C10	0.0147 (6)	0.0248 (7)	0.0195 (6)	0.0002 (5)	−0.0010 (5)	−0.0032 (5)
C11	0.0151 (6)	0.0220 (6)	0.0181 (6)	−0.0009 (5)	0.0001 (5)	−0.0016 (5)
C12	0.0186 (6)	0.0219 (7)	0.0234 (6)	0.0004 (5)	−0.0043 (5)	−0.0032 (5)
C13	0.0179 (6)	0.0205 (6)	0.0191 (6)	−0.0011 (5)	−0.0017 (5)	−0.0033 (5)
C14	0.0175 (6)	0.0161 (6)	0.0213 (6)	−0.0009 (5)	−0.0035 (5)	0.0011 (5)
C15	0.0188 (6)	0.0208 (6)	0.0188 (6)	−0.0010 (5)	−0.0004 (5)	−0.0008 (5)
C16	0.0209 (6)	0.0170 (6)	0.0169 (6)	−0.0011 (5)	−0.0045 (5)	0.0000 (5)
C17	0.0154 (6)	0.0172 (6)	0.0222 (6)	−0.0002 (5)	−0.0035 (5)	0.0010 (5)
C18	0.0189 (6)	0.0161 (6)	0.0188 (6)	0.0019 (5)	0.0001 (5)	0.0014 (5)
C19	0.0203 (6)	0.0184 (6)	0.0182 (6)	−0.0005 (5)	−0.0039 (5)	−0.0013 (5)
C20	0.0301 (8)	0.0429 (9)	0.0238 (7)	−0.0045 (6)	0.0039 (6)	−0.0126 (6)
C21	0.0220 (6)	0.0272 (7)	0.0292 (7)	−0.0074 (5)	−0.0013 (5)	0.0017 (6)
C22	0.0327 (8)	0.0358 (8)	0.0194 (6)	−0.0121 (6)	0.0029 (6)	−0.0063 (6)
C23	0.0174 (6)	0.0248 (7)	0.0206 (6)	−0.0017 (5)	−0.0005 (5)	0.0017 (5)
C24	0.0255 (7)	0.0226 (7)	0.0286 (7)	−0.0018 (5)	−0.0016 (6)	0.0014 (5)

O1—C23	1.2292 (16)	C10—C11	1.4685 (17)
O2—C18	1.3642 (16)	C11—C12	1.5040 (18)
O2—C20	1.4294 (16)	C12—C13	1.5424 (18)
O3—C17	1.3769 (15)	C12—H12A	0.9700
O3—C21	1.4255 (16)	C12—H12B	0.9700
O4—C16	1.3699 (15)	C13—C14	1.5155 (17)
O4—C22	1.4204 (16)	C13—H13	0.9800
N1—C11	1.2851 (17)	C14—C15	1.3913 (17)
N1—N2	1.3997 (14)	C14—C19	1.3913 (18)
N2—C23	1.3636 (17)	C15—C16	1.3957 (17)
N2—C13	1.4845 (16)	C15—H15	0.9300
C1—C10	1.3734 (19)	C16—C17	1.3894 (18)
C1—C2	1.4188 (18)	C17—C18	1.3994 (18)
C1—H1	0.9300	C18—C19	1.3953 (18)
C2—C3	1.419 (2)	C19—H19	0.9300
C2—C7	1.421 (2)	C20—H20A	0.9600
C3—C4	1.367 (2)	C20—H20B	0.9600
C3—H3	0.9300	C20—H20C	0.9600
C4—C5	1.405 (2)	C21—H21A	0.9600
C4—H4	0.9300	C21—H21B	0.9600
C5—C6	1.366 (2)	C21—H21C	0.9600
C5—H5	0.9300	C22—H22A	0.9600
C6—C7	1.4175 (19)	C22—H22B	0.9600
C6—H6	0.9300	C22—H22C	0.9600
C7—C8	1.420 (2)	C23—C24	1.5001 (19)
C8—C9	1.3565 (19)	C24—H24A	0.9600
C8—H8	0.9300	C24—H24B	0.9600
C9—C10	1.4210 (18)	C24—H24C	0.9600
C9—H9	0.9300
C18—O2—C20	117.62 (10)	N2—C13—H13	109.1
C17—O3—C21	114.09 (10)	C14—C13—H13	109.1
C16—O4—C22	117.66 (10)	C12—C13—H13	109.1
C11—N1—N2	107.97 (10)	C15—C14—C19	121.04 (11)
C23—N2—N1	120.09 (10)	C15—C14—C13	118.42 (11)
C23—N2—C13	123.58 (10)	C19—C14—C13	120.51 (11)
N1—N2—C13	112.62 (9)	C14—C15—C16	119.29 (12)
C10—C1—C2	121.38 (12)	C14—C15—H15	120.4
C10—C1—H1	119.3	C16—C15—H15	120.4
C2—C1—H1	119.3	O4—C16—C17	114.63 (11)
C1—C2—C3	122.49 (13)	O4—C16—C15	125.07 (12)
C1—C2—C7	118.68 (12)	C17—C16—C15	120.23 (11)
C3—C2—C7	118.82 (12)	O3—C17—C16	119.86 (11)
C4—C3—C2	120.61 (14)	O3—C17—C18	119.92 (11)
C4—C3—H3	119.7	C16—C17—C18	120.07 (11)
C2—C3—H3	119.7	O2—C18—C19	125.51 (11)
C3—C4—C5	120.53 (15)	O2—C18—C17	114.56 (11)
C3—C4—H4	119.7	C19—C18—C17	119.92 (12)
C5—C4—H4	119.7	C14—C19—C18	119.38 (11)
C6—C5—C4	120.36 (14)	C14—C19—H19	120.3
C6—C5—H5	119.8	C18—C19—H19	120.3
C4—C5—H5	119.8	O2—C20—H20A	109.5
C5—C6—C7	120.80 (15)	O2—C20—H20B	109.5
C5—C6—H6	119.6	H20A—C20—H20B	109.5
C7—C6—H6	119.6	O2—C20—H20C	109.5
C6—C7—C8	122.43 (13)	H20A—C20—H20C	109.5
C6—C7—C2	118.86 (14)	H20B—C20—H20C	109.5
C8—C7—C2	118.69 (12)	O3—C21—H21A	109.5
C9—C8—C7	121.31 (13)	O3—C21—H21B	109.5
C9—C8—H8	119.3	H21A—C21—H21B	109.5
C7—C8—H8	119.3	O3—C21—H21C	109.5
C8—C9—C10	120.58 (13)	H21A—C21—H21C	109.5
C8—C9—H9	119.7	H21B—C21—H21C	109.5
C10—C9—H9	119.7	O4—C22—H22A	109.5
C1—C10—C9	119.34 (12)	O4—C22—H22B	109.5
C1—C10—C11	120.81 (11)	H22A—C22—H22B	109.5
C9—C10—C11	119.84 (12)	O4—C22—H22C	109.5
N1—C11—C10	121.18 (11)	H22A—C22—H22C	109.5
N1—C11—C12	114.11 (11)	H22B—C22—H22C	109.5
C10—C11—C12	124.67 (11)	O1—C23—N2	120.02 (12)
C11—C12—C13	102.58 (10)	O1—C23—C24	122.63 (12)
C11—C12—H12A	111.3	N2—C23—C24	117.35 (11)
C13—C12—H12A	111.3	C23—C24—H24A	109.5
C11—C12—H12B	111.3	C23—C24—H24B	109.5
C13—C12—H12B	111.3	H24A—C24—H24B	109.5
H12A—C12—H12B	109.2	C23—C24—H24C	109.5
N2—C13—C14	113.80 (10)	H24A—C24—H24C	109.5
N2—C13—C12	100.80 (9)	H24B—C24—H24C	109.5
C14—C13—C12	114.71 (11)
C11—N1—N2—C23	−166.22 (12)	N1—N2—C13—C12	12.91 (13)
C11—N1—N2—C13	−7.16 (14)	C11—C12—C13—N2	−12.83 (12)
C10—C1—C2—C3	179.06 (12)	C11—C12—C13—C14	−135.52 (11)
C10—C1—C2—C7	−2.04 (19)	N2—C13—C14—C15	125.51 (12)
C1—C2—C3—C4	178.34 (12)	C12—C13—C14—C15	−119.12 (13)
C7—C2—C3—C4	−0.6 (2)	N2—C13—C14—C19	−56.38 (15)
C2—C3—C4—C5	−0.6 (2)	C12—C13—C14—C19	58.98 (15)
C3—C4—C5—C6	1.0 (2)	C19—C14—C15—C16	1.96 (19)
C4—C5—C6—C7	−0.2 (2)	C13—C14—C15—C16	−179.94 (11)
C5—C6—C7—C8	−179.35 (14)	C22—O4—C16—C17	173.08 (11)
C5—C6—C7—C2	−1.0 (2)	C22—O4—C16—C15	−3.84 (18)
C1—C2—C7—C6	−177.61 (12)	C14—C15—C16—O4	176.58 (11)
C3—C2—C7—C6	1.34 (19)	C14—C15—C16—C17	−0.18 (19)
C1—C2—C7—C8	0.84 (19)	C21—O3—C17—C16	83.24 (14)
C3—C2—C7—C8	179.79 (13)	C21—O3—C17—C18	−101.35 (13)
C6—C7—C8—C9	178.77 (13)	O4—C16—C17—O3	−3.74 (16)
C2—C7—C8—C9	0.4 (2)	C15—C16—C17—O3	173.34 (11)
C7—C8—C9—C10	−0.5 (2)	O4—C16—C17—C18	−179.15 (11)
C2—C1—C10—C9	1.98 (19)	C15—C16—C17—C18	−2.06 (18)
C2—C1—C10—C11	−179.40 (11)	C20—O2—C18—C19	9.38 (18)
C8—C9—C10—C1	−0.7 (2)	C20—O2—C18—C17	−171.42 (12)
C8—C9—C10—C11	−179.35 (12)	O3—C17—C18—O2	7.90 (16)
N2—N1—C11—C10	179.66 (10)	C16—C17—C18—O2	−176.70 (10)
N2—N1—C11—C12	−2.55 (14)	O3—C17—C18—C19	−172.85 (11)
C1—C10—C11—N1	162.71 (12)	C16—C17—C18—C19	2.55 (18)
C9—C10—C11—N1	−18.67 (19)	C15—C14—C19—C18	−1.47 (18)
C1—C10—C11—C12	−14.84 (19)	C13—C14—C19—C18	−179.53 (11)
C9—C10—C11—C12	163.78 (12)	O2—C18—C19—C14	178.36 (11)
N1—C11—C12—C13	10.43 (14)	C17—C18—C19—C14	−0.80 (18)
C10—C11—C12—C13	−171.87 (11)	N1—N2—C23—O1	166.45 (11)
C23—N2—C13—C14	−65.56 (16)	C13—N2—C23—O1	9.77 (19)
N1—N2—C13—C14	136.22 (11)	N1—N2—C23—C24	−14.40 (17)
C23—N2—C13—C12	171.12 (11)	C13—N2—C23—C24	−171.08 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O4i	0.93	2.48	3.3327 (19)	152
C8—H8···O3ii	0.93	2.57	3.4320 (19)	155
C12—H12A···O1iii	0.97	2.55	3.3359 (18)	138
C19—H19···O1iii	0.93	2.53	3.3073 (18)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O4i	0.93	2.48	3.3327 (19)	152
C8—H8⋯O3ii	0.93	2.57	3.4320 (19)	155
C12—H12A⋯O1iii	0.97	2.55	3.3359 (18)	138
C19—H19⋯O1iii	0.93	2.53	3.3073 (18)	141

Symmetry codes: (i) ; (ii) ; (iii) .