Diethyl 2-[(3,5-dimethyl-1H-pyrazol-1-yl)(4-meth-oxy-phen-yl)meth-yl]propane-dioate.

The title compound, C(20)H(26)N(2)O(5), was prepared in good yield (76%) through condensation of diethyl (4-meth-oxy-benz-yl)propane-dioate with 3,5-dimethyl-1H-pyrazole. The dihedral between the benzene and pyrazole rings is 83.96 (10)°. The crystal packing is stabilized by a C-H⋯O inter-action, which links the mol-ecules into centrosymmetric dimers.

Related literature

For related compounds displaying biological activity, see: Dayam et al. (2007 ▶); Patil et al. (2007 ▶); Ramkumar et al. (2008 ▶); Sechi et al. (2009 ▶) & Zeng et al. (2008 ▶). For the synthetic procedure, see: Pommier & Neamati (2006 ▶).

Experimental

Crystal data

C20H26N2O5

M = 374.43

Monoclinic,

a = 11.9618 (3) Å

b = 7.9681 (2) Å

c = 21.1269 (6) Å

β = 96.504 (1)°

V = 2000.70 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.23 × 0.17 × 0.14 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

18616 measured reflections

3921 independent reflections

3177 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.154

S = 1.05

3921 reflections

249 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810025572/bt5280sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810025572/bt5280Isup2.hkl

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

Enhanced figure: interactive version of Fig. 3

C20H26N2O5	F(000) = 800
Mr = 374.43	Dx = 1.243 Mg m−3
Monoclinic, P21/c	Melting point: 361 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.9618 (3) Å	Cell parameters from 2174 reflections
b = 7.9681 (2) Å	θ = 2.3–27.1°
c = 21.1269 (6) Å	µ = 0.09 mm−1
β = 96.504 (1)°	T = 296 K
V = 2000.70 (9) Å3	Block, colourless
Z = 4	0.23 × 0.17 × 0.14 mm

Bruker X8 APEXII CCD area-detector diffractometer	3177 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
graphite	θmax = 26.0°, θmin = 2.7°
φ and ω scans	h = −14→14
18616 measured reflections	k = −9→9
3921 independent reflections	l = −26→26

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0687P)2 + 1.8319P] where P = (Fo2 + 2Fc2)/3
3921 reflections	(Δ/σ)max = 0.007
249 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

Experimental. The data collection nominally covered a sphere of reciprocal space, by a combination of tree sets of exposures; each set had a different φ angle for the crystal and each exposure covered 0.5° in ω and 20 s in time. The crystal-to-detector distance was 37.5 mm.

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
O2	0.40914 (11)	−0.14261 (19)	0.44322 (7)	0.0301 (3)
O3	0.26937 (12)	−0.19794 (18)	0.36564 (7)	0.0321 (4)
O4	0.39768 (14)	0.2442 (2)	0.36381 (8)	0.0441 (4)
O5	0.23951 (15)	0.1580 (2)	0.30637 (7)	0.0446 (4)
O1	0.16987 (15)	−0.2065 (2)	0.68944 (8)	0.0468 (5)
N1	0.25069 (14)	0.3219 (2)	0.47437 (8)	0.0252 (4)
N2	0.15274 (14)	0.3525 (2)	0.43620 (8)	0.0297 (4)
C1	0.29918 (16)	0.1528 (2)	0.47752 (9)	0.0230 (4)
H1	0.3813	0.1633	0.4845	0.028*
C2	0.26772 (16)	0.0673 (3)	0.41296 (9)	0.0244 (4)
H2	0.1859	0.0541	0.4051	0.029*
C11	0.26097 (16)	0.0542 (2)	0.53261 (9)	0.0229 (4)
C3	0.32439 (16)	−0.1032 (2)	0.41081 (9)	0.0239 (4)
C12	0.33950 (17)	−0.0251 (3)	0.57616 (9)	0.0277 (4)
H12	0.4154	−0.0197	0.5706	0.033*
C21	0.28468 (17)	0.4563 (3)	0.51094 (10)	0.0285 (5)
C16	0.14790 (16)	0.0419 (3)	0.54174 (10)	0.0277 (4)
H16	0.0941	0.0929	0.5127	0.033*
C13	0.30680 (18)	−0.1116 (3)	0.62736 (10)	0.0323 (5)
H13	0.3605	−0.1643	0.6559	0.039*
C14	0.19347 (18)	−0.1206 (3)	0.63658 (10)	0.0311 (5)
C15	0.11364 (17)	−0.0445 (3)	0.59307 (10)	0.0312 (5)
H15	0.0376	−0.0515	0.5983	0.037*
C6	0.30985 (19)	0.1697 (3)	0.35912 (10)	0.0308 (5)
C23	0.12710 (18)	0.5105 (3)	0.44907 (11)	0.0322 (5)
C4	0.32363 (19)	−0.3556 (3)	0.35159 (12)	0.0370 (5)
H4A	0.2679	−0.4329	0.3314	0.044*
H4B	0.3575	−0.4063	0.3909	0.044*
C22	0.20634 (18)	0.5797 (3)	0.49546 (10)	0.0330 (5)
H22	0.2060	0.6874	0.5124	0.040*
C5	0.4121 (2)	−0.3243 (4)	0.30837 (11)	0.0466 (6)
H5A	0.3789	−0.2693	0.2704	0.070*
H5B	0.4442	−0.4292	0.2973	0.070*
H5C	0.4699	−0.2542	0.3296	0.070*
C25	0.3888 (2)	0.4563 (3)	0.55689 (12)	0.0416 (6)
H25A	0.3743	0.4000	0.5953	0.062*
H25B	0.4114	0.5699	0.5666	0.062*
H25C	0.4478	0.3990	0.5384	0.062*
C7	0.2781 (3)	0.2351 (4)	0.24975 (12)	0.0612 (8)
H7A	0.2695	0.3560	0.2515	0.073*
H7B	0.3571	0.2098	0.2481	0.073*
C24	0.0258 (2)	0.5924 (3)	0.41410 (14)	0.0489 (7)
H24A	0.0493	0.6722	0.3842	0.073*
H24B	−0.0160	0.6490	0.4439	0.073*
H24C	−0.0209	0.5086	0.3917	0.073*
C17	0.0566 (2)	−0.2040 (4)	0.70479 (13)	0.0545 (7)
H17A	0.0335	−0.0900	0.7101	0.082*
H17B	0.0521	−0.2649	0.7436	0.082*
H17C	0.0081	−0.2554	0.6709	0.082*
C8	0.2127 (3)	0.1700 (5)	0.19471 (13)	0.0731 (10)
H8A	0.2245	0.0511	0.1922	0.110*
H8B	0.2351	0.2230	0.1573	0.110*
H8C	0.1345	0.1919	0.1975	0.110*

	U11	U22	U33	U12	U13	U23
O2	0.0249 (7)	0.0292 (8)	0.0357 (8)	0.0049 (6)	0.0007 (6)	−0.0048 (6)
O3	0.0317 (8)	0.0265 (8)	0.0371 (8)	0.0009 (6)	−0.0005 (6)	−0.0089 (6)
O4	0.0466 (10)	0.0436 (10)	0.0435 (9)	−0.0125 (8)	0.0117 (8)	0.0046 (8)
O5	0.0624 (11)	0.0441 (10)	0.0264 (8)	−0.0085 (8)	0.0010 (7)	0.0036 (7)
O1	0.0475 (10)	0.0586 (12)	0.0360 (9)	−0.0031 (9)	0.0117 (7)	0.0143 (8)
N1	0.0258 (8)	0.0229 (9)	0.0265 (8)	0.0027 (7)	0.0013 (7)	−0.0005 (7)
N2	0.0280 (9)	0.0278 (9)	0.0330 (9)	0.0061 (7)	0.0015 (7)	0.0008 (7)
C1	0.0216 (9)	0.0196 (9)	0.0277 (10)	0.0025 (7)	0.0022 (7)	−0.0011 (8)
C2	0.0221 (9)	0.0238 (10)	0.0273 (10)	0.0019 (8)	0.0031 (8)	−0.0012 (8)
C11	0.0242 (9)	0.0203 (10)	0.0246 (9)	0.0011 (8)	0.0036 (7)	−0.0037 (7)
C3	0.0230 (10)	0.0237 (10)	0.0257 (9)	−0.0028 (8)	0.0067 (8)	−0.0018 (8)
C12	0.0228 (10)	0.0311 (11)	0.0287 (10)	0.0005 (8)	0.0009 (8)	−0.0014 (8)
C21	0.0320 (11)	0.0253 (11)	0.0294 (10)	−0.0012 (8)	0.0088 (8)	−0.0025 (8)
C16	0.0242 (10)	0.0293 (11)	0.0292 (10)	0.0060 (8)	0.0014 (8)	−0.0008 (8)
C13	0.0315 (11)	0.0372 (13)	0.0268 (10)	0.0019 (9)	−0.0022 (8)	0.0033 (9)
C14	0.0379 (12)	0.0310 (12)	0.0253 (10)	−0.0017 (9)	0.0073 (9)	0.0011 (8)
C15	0.0255 (10)	0.0350 (12)	0.0340 (11)	0.0006 (9)	0.0078 (8)	−0.0019 (9)
C6	0.0405 (12)	0.0244 (11)	0.0277 (10)	0.0041 (9)	0.0041 (9)	−0.0028 (8)
C23	0.0340 (11)	0.0253 (11)	0.0385 (11)	0.0075 (9)	0.0100 (9)	0.0030 (9)
C4	0.0369 (12)	0.0279 (11)	0.0454 (13)	0.0010 (9)	0.0015 (10)	−0.0159 (10)
C22	0.0401 (12)	0.0222 (10)	0.0384 (12)	0.0037 (9)	0.0122 (10)	−0.0033 (9)
C5	0.0504 (15)	0.0548 (16)	0.0350 (12)	0.0052 (12)	0.0069 (11)	−0.0127 (12)
C25	0.0425 (13)	0.0381 (13)	0.0423 (13)	−0.0001 (11)	−0.0034 (10)	−0.0091 (11)
C7	0.097 (2)	0.0572 (18)	0.0293 (13)	−0.0235 (17)	0.0078 (14)	0.0054 (12)
C24	0.0432 (14)	0.0413 (15)	0.0613 (16)	0.0180 (11)	0.0019 (12)	0.0046 (13)
C17	0.0596 (17)	0.0595 (18)	0.0492 (15)	−0.0086 (14)	0.0274 (13)	0.0059 (13)
C8	0.113 (3)	0.072 (2)	0.0346 (14)	−0.033 (2)	0.0104 (16)	−0.0004 (14)

O2—C3	1.199 (2)	C13—H13	0.9300
O3—C3	1.331 (2)	C14—C15	1.388 (3)
O3—C4	1.460 (3)	C15—H15	0.9300
O4—C6	1.201 (3)	C23—C22	1.397 (3)
O5—C6	1.322 (3)	C23—C24	1.496 (3)
O5—C7	1.465 (3)	C4—C5	1.495 (3)
O1—C14	1.367 (3)	C4—H4A	0.9700
O1—C17	1.428 (3)	C4—H4B	0.9700
N1—C21	1.355 (3)	C22—H22	0.9300
N1—N2	1.367 (2)	C5—H5A	0.9600
N1—C1	1.466 (2)	C5—H5B	0.9600
N2—C23	1.331 (3)	C5—H5C	0.9600
C1—C11	1.517 (3)	C25—H25A	0.9600
C1—C2	1.533 (3)	C25—H25B	0.9600
C1—H1	0.9800	C25—H25C	0.9600
C2—C3	1.521 (3)	C7—C8	1.424 (4)
C2—C6	1.531 (3)	C7—H7A	0.9700
C2—H2	0.9800	C7—H7B	0.9700
C11—C12	1.390 (3)	C24—H24A	0.9600
C11—C16	1.391 (3)	C24—H24B	0.9600
C12—C13	1.376 (3)	C24—H24C	0.9600
C12—H12	0.9300	C17—H17A	0.9600
C21—C22	1.372 (3)	C17—H17B	0.9600
C21—C25	1.490 (3)	C17—H17C	0.9600
C16—C15	1.385 (3)	C8—H8A	0.9600
C16—H16	0.9300	C8—H8B	0.9600
C13—C14	1.393 (3)	C8—H8C	0.9600
C3—O3—C4	116.03 (16)	N2—C23—C24	120.3 (2)
C6—O5—C7	115.4 (2)	C22—C23—C24	128.4 (2)
C14—O1—C17	117.87 (19)	O3—C4—C5	110.0 (2)
C21—N1—N2	112.18 (17)	O3—C4—H4A	109.7
C21—N1—C1	127.50 (16)	C5—C4—H4A	109.7
N2—N1—C1	119.92 (16)	O3—C4—H4B	109.7
C23—N2—N1	104.46 (17)	C5—C4—H4B	109.7
N1—C1—C11	111.05 (15)	H4A—C4—H4B	108.2
N1—C1—C2	108.18 (15)	C21—C22—C23	105.97 (19)
C11—C1—C2	112.80 (16)	C21—C22—H22	127.0
N1—C1—H1	108.2	C23—C22—H22	127.0
C11—C1—H1	108.2	C4—C5—H5A	109.5
C2—C1—H1	108.2	C4—C5—H5B	109.5
C3—C2—C6	105.57 (15)	H5A—C5—H5B	109.5
C3—C2—C1	110.98 (16)	C4—C5—H5C	109.5
C6—C2—C1	110.86 (16)	H5A—C5—H5C	109.5
C3—C2—H2	109.8	H5B—C5—H5C	109.5
C6—C2—H2	109.8	C21—C25—H25A	109.5
C1—C2—H2	109.8	C21—C25—H25B	109.5
C12—C11—C16	118.10 (18)	H25A—C25—H25B	109.5
C12—C11—C1	120.23 (17)	C21—C25—H25C	109.5
C16—C11—C1	121.66 (17)	H25A—C25—H25C	109.5
O2—C3—O3	125.32 (19)	H25B—C25—H25C	109.5
O2—C3—C2	124.59 (18)	C8—C7—O5	108.6 (2)
O3—C3—C2	110.01 (16)	C8—C7—H7A	110.0
C13—C12—C11	121.13 (19)	O5—C7—H7A	110.0
C13—C12—H12	119.4	C8—C7—H7B	110.0
C11—C12—H12	119.4	O5—C7—H7B	110.0
N1—C21—C22	106.12 (18)	H7A—C7—H7B	108.3
N1—C21—C25	123.09 (19)	C23—C24—H24A	109.5
C22—C21—C25	130.8 (2)	C23—C24—H24B	109.5
C15—C16—C11	121.46 (19)	H24A—C24—H24B	109.5
C15—C16—H16	119.3	C23—C24—H24C	109.5
C11—C16—H16	119.3	H24A—C24—H24C	109.5
C12—C13—C14	120.21 (19)	H24B—C24—H24C	109.5
C12—C13—H13	119.9	O1—C17—H17A	109.5
C14—C13—H13	119.9	O1—C17—H17B	109.5
O1—C14—C15	124.7 (2)	H17A—C17—H17B	109.5
O1—C14—C13	115.74 (19)	O1—C17—H17C	109.5
C15—C14—C13	119.52 (19)	H17A—C17—H17C	109.5
C16—C15—C14	119.56 (19)	H17B—C17—H17C	109.5
C16—C15—H15	120.2	C7—C8—H8A	109.5
C14—C15—H15	120.2	C7—C8—H8B	109.5
O4—C6—O5	124.9 (2)	H8A—C8—H8B	109.5
O4—C6—C2	124.10 (19)	C7—C8—H8C	109.5
O5—C6—C2	110.92 (18)	H8A—C8—H8C	109.5
N2—C23—C22	111.27 (19)	H8B—C8—H8C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2i	0.93	2.51	3.358 (3)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2i	0.93	2.51	3.358 (3)	152

Symmetry code: (i) .