Ethyl 5-[(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)imino­meth­yl]-3,4-dimethyl-1H-pyrrole-2-carboxyl­ate

Wang, Y.; Wu, W.-N.; Wang, Q.-F.

doi:10.1107/S1600536809027780

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1933

doi:10.1107/S1600536809027780

Open

access

Ethyl 5-[(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)iminomethyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate

Yuan Wang,^a Wei-Na Wu ^a ^* and Qiu-Fen Wang ^a

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China
^*Correspondence e-mail: wuwn08@hpu.edu.cn

(Received 9 July 2009; accepted 15 July 2009; online 18 July 2009)

In the title compound, C₂₁H₂₄N₄O₃, the molecule has an E configuration about the imine C=N double bond. Intermolecular N—H⋯O hydrogen bonds assemble molecules into centrosymmetric dimers.

Related literature

For studies on the complexes of bis(pyrrol-2-yl-methyleneamine) ligands, see: Wang et al. (2008 ); Yang et al. (2003 ). For the structure of 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate, see: Wu et al. (2009 ).

Experimental

Crystal data

C₂₁H₂₄N₄O₃
M_r = 380.44
Monoclinic, P 2₁ /c
a = 13.421 (2) Å
b = 20.141 (3) Å
c = 7.5477 (13) Å
β = 96.147 (2)°
V = 2028.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.21 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.979, T_max = 0.993
23826 measured reflections
4717 independent reflections
2622 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.149
S = 1.01
4717 reflections
258 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1D⋯O2ⁱ	0.86	2.05	2.880 (2)	163
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027780/gk2222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809027780/gk2222Isup2.hkl

checkCIF report

Comment top

Due to the excellent fluorescent properties and good solubilities of their complexes, linear spaced bis(pyrrol-2-yl-methyleneamine) ligands have attracted much recent attention (Yang et al., 2003). As part of our ongoing studies of pyrrol-2-yl-methyleneamine ligand (Wu et al., 2008), the title compound was synthesized and characterized by X-ray diffraction.

In the title compound (Fig. 1), the molecule adopts an E configuration at the C=N double bond. The dihedral angle between dihydropyrazole ring (N3,4/C11–C13, r.m.s. deviation 0.026 Å) and pyrrole ring (N1/C4–C7, r.m.s. deviation 0.002 Å) is 9.6 (2)°. The phenyl ring (C16–C20) makes the dihedral angle of 42.4 (1)° with dihydropyrazole ring. In the crystal, th molecules are linked into a centrosymmetric dimer by two intermolecular N—H···O hydrogen bonds, forming a R₂²(10) ring motif (Table1, Fig. 2). The dimers stack alternately like letter "V" (Fig. 3) and the dihedral angle of the adjacent phenyl rings is 37.1 (3)°. Intermolecular C14—H14A···π (N1/C4–C7) interaction (C14-centroid distance 3.4992 Å). is also present.

Related literature top

For studies on the complexes of bis(pyrrol-2-yl-methyleneamine) ligands, see: Wang et al. (2008); Yang et al. (2003). For the structure of 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate, see: Wu et al. (2009).

Experimental top

4-Amino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (0.203 g, 1 mmol) was dissolved in ethanol (10 ml), then an ethanol solution (10 ml) containing ethyl 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate (0.195 g, 1 mmol) was added dropwise at room temperature. After stirring for 24 h, the precipitate was separated from the solution by suction filtration, washed with ethanol, and dried in a vacuum to yield the title compound 0.198 g (52%).Yellow blocks of the title compound were obtained by slow evaporation of an ethanol/THF (1:1) solution.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure shown with 50% probability displacement ellipsoids.
	Fig. 2. A centrosymmetric dimer via intermolecular hydrogen bonds (dashed lines)..
	Fig. 3. The crystal packing for the title compound viewed down the a axis

Ethyl 5-[(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4- yl)iminomethyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate top

Crystal data top

C₂₁H₂₄N₄O₃	F(000) = 808
M_r = 380.44	D_x = 1.246 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2702 reflections
a = 13.421 (2) Å	θ = 2.5–20.3°
b = 20.141 (3) Å	µ = 0.09 mm⁻¹
c = 7.5477 (13) Å	T = 296 K
β = 96.147 (2)°	Block, yellow
V = 2028.5 (6) Å³	0.30 × 0.21 × 0.08 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4717 independent reflections
Radiation source: fine-focus sealed tube	2622 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 27.8°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −17→17
T_min = 0.979, T_max = 0.993	k = −26→26
23826 measured reflections	l = −9→9

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.07P)² + 0.1292P] where P = (F_o² + 2F_c²)/3
4717 reflections	(Δ/σ)_max < 0.001
258 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₁H₂₄N₄O₃	V = 2028.5 (6) Å³
M_r = 380.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.421 (2) Å	µ = 0.09 mm⁻¹
b = 20.141 (3) Å	T = 296 K
c = 7.5477 (13) Å	0.30 × 0.21 × 0.08 mm
β = 96.147 (2)°

Data collection top

Bruker SMART CCD diffractometer	4717 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	2622 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.993	R_int = 0.051
23826 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.149	H-atom parameters constrained
S = 1.01	Δρ_max = 0.20 e Å⁻³
4717 reflections	Δρ_min = −0.20 e Å⁻³
258 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	0.89926 (11)	0.04791 (7)	0.2730 (2)	0.0489 (4)
H1D	0.9557	0.0297	0.3094	0.059*
O3	0.73311 (9)	0.00819 (7)	0.59614 (18)	0.0606 (4)
O2	0.89663 (10)	−0.01469 (7)	0.60113 (19)	0.0637 (4)
C3	0.82077 (14)	0.01047 (9)	0.5289 (3)	0.0489 (5)
N4	1.09462 (11)	0.18926 (7)	−0.46225 (19)	0.0497 (4)
N2	0.94408 (12)	0.13164 (8)	−0.1322 (2)	0.0525 (4)
C11	1.02102 (14)	0.14408 (9)	−0.2378 (2)	0.0475 (4)
C10	0.95909 (14)	0.09456 (9)	0.0064 (2)	0.0493 (5)
H10A	1.0211	0.0744	0.0341	0.059*
C4	0.81529 (13)	0.04502 (9)	0.3599 (3)	0.0498 (5)
C13	1.00552 (14)	0.17709 (8)	−0.3956 (2)	0.0477 (4)
C5	0.88044 (13)	0.08391 (9)	0.1198 (2)	0.0491 (5)
O1	1.17701 (10)	0.11051 (8)	−0.06507 (18)	0.0692 (4)
N3	1.16917 (11)	0.15719 (8)	−0.3468 (2)	0.0530 (4)
C12	1.12710 (15)	0.13275 (9)	−0.1985 (2)	0.0514 (5)
C21	1.30141 (16)	0.23522 (10)	−0.4062 (3)	0.0590 (5)
H21	1.2540	0.2680	−0.4377	0.071*
C16	1.27191 (14)	0.17312 (10)	−0.3532 (2)	0.0525 (5)
C6	0.78108 (14)	0.10470 (10)	0.1085 (3)	0.0548 (5)
C2	0.73181 (15)	−0.02886 (11)	0.7614 (3)	0.0643 (6)
H2A	0.7713	−0.0059	0.8577	0.077*
H2B	0.7604	−0.0726	0.7489	0.077*
C7	0.74006 (13)	0.08006 (10)	0.2585 (3)	0.0568 (5)
C17	1.34292 (17)	0.12484 (11)	−0.3051 (3)	0.0674 (6)
H17	1.3233	0.0831	−0.2693	0.081*
C14	0.90956 (15)	0.20130 (10)	−0.4891 (3)	0.0620 (5)
H14A	0.8951	0.1776	−0.5992	0.093*
H14B	0.9149	0.2479	−0.5134	0.093*
H14C	0.8566	0.1941	−0.4153	0.093*
C8	0.72684 (15)	0.14606 (12)	−0.0377 (3)	0.0767 (7)
H8A	0.6559	0.1425	−0.0328	0.115*
H8B	0.7433	0.1304	−0.1512	0.115*
H8C	0.7468	0.1916	−0.0224	0.115*
C15	1.10435 (16)	0.18288 (10)	−0.6526 (2)	0.0603 (5)
H15A	1.0997	0.1369	−0.6861	0.091*
H15B	1.1681	0.2002	−0.6772	0.091*
H15C	1.0517	0.2074	−0.7195	0.091*
C20	1.40162 (18)	0.24783 (13)	−0.4116 (3)	0.0772 (7)
H20	1.4217	0.2893	−0.4485	0.093*
C9	0.63467 (16)	0.09116 (14)	0.3014 (4)	0.0903 (9)
H9A	0.6286	0.1353	0.3469	0.135*
H9B	0.6189	0.0596	0.3895	0.135*
H9C	0.5891	0.0857	0.1954	0.135*
C19	1.47261 (19)	0.20031 (16)	−0.3638 (4)	0.0883 (8)
H19	1.5403	0.2095	−0.3673	0.106*
C18	1.44268 (19)	0.13905 (14)	−0.3105 (4)	0.0855 (8)
H18	1.4905	0.1067	−0.2777	0.103*
C1	0.62731 (18)	−0.03477 (16)	0.8013 (4)	0.1050 (10)
H1A	0.6035	0.0079	0.8348	0.157*
H1B	0.6237	−0.0655	0.8976	0.157*
H1C	0.5865	−0.0505	0.6976	0.157*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0397 (8)	0.0527 (9)	0.0546 (10)	−0.0008 (7)	0.0066 (7)	0.0072 (7)
O3	0.0435 (7)	0.0775 (9)	0.0624 (9)	0.0040 (6)	0.0131 (6)	0.0224 (7)
O2	0.0434 (8)	0.0757 (10)	0.0724 (10)	0.0066 (7)	0.0081 (7)	0.0203 (7)
C3	0.0405 (10)	0.0491 (11)	0.0578 (12)	−0.0047 (8)	0.0087 (9)	0.0025 (9)
N4	0.0550 (10)	0.0537 (9)	0.0399 (9)	0.0003 (7)	0.0025 (7)	0.0056 (7)
N2	0.0564 (10)	0.0528 (9)	0.0482 (9)	−0.0069 (7)	0.0058 (8)	0.0030 (8)
C11	0.0518 (11)	0.0460 (10)	0.0450 (11)	−0.0055 (8)	0.0061 (8)	0.0008 (8)
C10	0.0479 (11)	0.0499 (11)	0.0500 (11)	−0.0051 (8)	0.0048 (9)	−0.0004 (9)
C4	0.0383 (10)	0.0536 (11)	0.0578 (12)	−0.0046 (8)	0.0065 (8)	0.0067 (9)
C13	0.0542 (11)	0.0418 (10)	0.0463 (11)	−0.0030 (8)	0.0018 (9)	−0.0016 (8)
C5	0.0484 (11)	0.0502 (11)	0.0483 (11)	−0.0068 (8)	0.0028 (8)	0.0020 (9)
O1	0.0629 (9)	0.0895 (11)	0.0536 (9)	0.0007 (8)	−0.0006 (7)	0.0250 (8)
N3	0.0522 (10)	0.0610 (10)	0.0449 (9)	0.0004 (8)	0.0015 (7)	0.0101 (8)
C12	0.0590 (12)	0.0524 (11)	0.0425 (11)	−0.0035 (9)	0.0048 (9)	0.0066 (9)
C21	0.0619 (13)	0.0662 (14)	0.0510 (12)	−0.0007 (10)	0.0154 (10)	0.0034 (10)
C16	0.0536 (12)	0.0608 (12)	0.0435 (10)	−0.0006 (9)	0.0078 (9)	−0.0018 (9)
C6	0.0438 (11)	0.0610 (12)	0.0580 (12)	−0.0050 (9)	−0.0018 (9)	0.0093 (10)
C2	0.0563 (12)	0.0795 (15)	0.0589 (13)	0.0055 (11)	0.0142 (10)	0.0197 (11)
C7	0.0402 (10)	0.0644 (13)	0.0653 (13)	−0.0036 (9)	0.0033 (9)	0.0100 (10)
C17	0.0686 (15)	0.0661 (14)	0.0673 (15)	0.0066 (11)	0.0061 (11)	0.0011 (11)
C14	0.0622 (13)	0.0608 (12)	0.0610 (13)	−0.0004 (10)	−0.0020 (10)	0.0048 (10)
C8	0.0532 (13)	0.0964 (18)	0.0782 (16)	−0.0009 (12)	−0.0035 (11)	0.0289 (14)
C15	0.0747 (14)	0.0643 (13)	0.0417 (11)	0.0035 (11)	0.0049 (10)	0.0040 (10)
C20	0.0709 (16)	0.0917 (17)	0.0721 (16)	−0.0158 (14)	0.0214 (12)	0.0067 (13)
C9	0.0450 (13)	0.122 (2)	0.105 (2)	0.0141 (13)	0.0165 (13)	0.0387 (17)
C19	0.0566 (15)	0.120 (2)	0.0905 (19)	−0.0054 (16)	0.0181 (13)	−0.0016 (17)
C18	0.0608 (16)	0.104 (2)	0.0924 (19)	0.0211 (14)	0.0100 (13)	0.0017 (16)
C1	0.0648 (16)	0.146 (3)	0.108 (2)	−0.0029 (16)	0.0275 (15)	0.0547 (19)

Geometric parameters (Å, º) top

N1—C4	1.364 (2)	C6—C8	1.507 (3)
N1—C5	1.366 (2)	C2—C1	1.471 (3)
N1—H1D	0.8600	C2—H2A	0.9700
O3—C3	1.331 (2)	C2—H2B	0.9700
O3—C2	1.455 (2)	C7—C9	1.501 (3)
O2—C3	1.213 (2)	C17—C18	1.374 (3)
C3—C4	1.448 (3)	C17—H17	0.9300
N4—C13	1.368 (2)	C14—H14A	0.9600
N4—N3	1.411 (2)	C14—H14B	0.9600
N4—C15	1.462 (2)	C14—H14C	0.9600
N2—C10	1.284 (2)	C8—H8A	0.9600
N2—C11	1.393 (2)	C8—H8B	0.9600
C11—C13	1.361 (2)	C8—H8C	0.9600
C11—C12	1.441 (3)	C15—H15A	0.9600
C10—C5	1.444 (3)	C15—H15B	0.9600
C10—H10A	0.9300	C15—H15C	0.9600
C4—C7	1.392 (3)	C20—C19	1.371 (3)
C13—C14	1.483 (3)	C20—H20	0.9300
C5—C6	1.392 (3)	C9—H9A	0.9600
O1—C12	1.233 (2)	C9—H9B	0.9600
N3—C12	1.396 (2)	C9—H9C	0.9600
N3—C16	1.422 (2)	C19—C18	1.371 (4)
C21—C20	1.374 (3)	C19—H19	0.9300
C21—C16	1.384 (3)	C18—H18	0.9300
C21—H21	0.9300	C1—H1A	0.9600
C16—C17	1.383 (3)	C1—H1B	0.9600
C6—C7	1.402 (3)	C1—H1C	0.9600

C4—N1—C5	110.02 (15)	H2A—C2—H2B	108.4
C4—N1—H1D	125.0	C4—C7—C6	107.40 (16)
C5—N1—H1D	125.0	C4—C7—C9	126.99 (18)
C3—O3—C2	115.88 (15)	C6—C7—C9	125.61 (18)
O2—C3—O3	123.23 (18)	C18—C17—C16	119.5 (2)
O2—C3—C4	123.89 (17)	C18—C17—H17	120.3
O3—C3—C4	112.88 (16)	C16—C17—H17	120.3
C13—N4—N3	106.31 (14)	C13—C14—H14A	109.5
C13—N4—C15	121.26 (15)	C13—C14—H14B	109.5
N3—N4—C15	115.75 (15)	H14A—C14—H14B	109.5
C10—N2—C11	120.64 (17)	C13—C14—H14C	109.5
C13—C11—N2	122.38 (17)	H14A—C14—H14C	109.5
C13—C11—C12	108.20 (16)	H14B—C14—H14C	109.5
N2—C11—C12	129.10 (16)	C6—C8—H8A	109.5
N2—C10—C5	120.56 (18)	C6—C8—H8B	109.5
N2—C10—H10A	119.7	H8A—C8—H8B	109.5
C5—C10—H10A	119.7	C6—C8—H8C	109.5
N1—C4—C7	107.58 (16)	H8A—C8—H8C	109.5
N1—C4—C3	118.50 (16)	H8B—C8—H8C	109.5
C7—C4—C3	133.90 (17)	N4—C15—H15A	109.5
C11—C13—N4	110.59 (16)	N4—C15—H15B	109.5
C11—C13—C14	128.38 (18)	H15A—C15—H15B	109.5
N4—C13—C14	120.98 (16)	N4—C15—H15C	109.5
N1—C5—C6	107.48 (16)	H15A—C15—H15C	109.5
N1—C5—C10	120.00 (16)	H15B—C15—H15C	109.5
C6—C5—C10	132.51 (18)	C21—C20—C19	121.2 (2)
C12—N3—N4	109.60 (15)	C21—C20—H20	119.4
C12—N3—C16	125.72 (15)	C19—C20—H20	119.4
N4—N3—C16	120.13 (15)	C7—C9—H9A	109.5
O1—C12—N3	123.51 (18)	C7—C9—H9B	109.5
O1—C12—C11	131.60 (17)	H9A—C9—H9B	109.5
N3—C12—C11	104.78 (15)	C7—C9—H9C	109.5
C20—C21—C16	119.1 (2)	H9A—C9—H9C	109.5
C20—C21—H21	120.4	H9B—C9—H9C	109.5
C16—C21—H21	120.4	C18—C19—C20	119.2 (2)
C17—C16—C21	120.1 (2)	C18—C19—H19	120.4
C17—C16—N3	118.44 (18)	C20—C19—H19	120.4
C21—C16—N3	121.49 (18)	C19—C18—C17	120.9 (2)
C5—C6—C7	107.52 (16)	C19—C18—H18	119.6
C5—C6—C8	126.55 (18)	C17—C18—H18	119.6
C7—C6—C8	125.93 (18)	C2—C1—H1A	109.5
O3—C2—C1	108.44 (17)	C2—C1—H1B	109.5
O3—C2—H2A	110.0	H1A—C1—H1B	109.5
C1—C2—H2A	110.0	C2—C1—H1C	109.5
O3—C2—H2B	110.0	H1A—C1—H1C	109.5
C1—C2—H2B	110.0	H1B—C1—H1C	109.5

C2—O3—C3—O2	−2.1 (3)	C16—N3—C12—C11	162.58 (17)
C2—O3—C3—C4	176.86 (16)	C13—C11—C12—O1	172.6 (2)
C10—N2—C11—C13	172.78 (17)	N2—C11—C12—O1	−0.9 (3)
C10—N2—C11—C12	−14.5 (3)	C13—C11—C12—N3	−3.6 (2)
C11—N2—C10—C5	177.46 (16)	N2—C11—C12—N3	−177.11 (17)
C5—N1—C4—C7	0.3 (2)	C20—C21—C16—C17	0.6 (3)
C5—N1—C4—C3	−178.24 (16)	C20—C21—C16—N3	−179.38 (18)
O2—C3—C4—N1	2.1 (3)	C12—N3—C16—C17	54.9 (3)
O3—C3—C4—N1	−176.84 (16)	N4—N3—C16—C17	−151.52 (18)
O2—C3—C4—C7	−175.9 (2)	C12—N3—C16—C21	−125.1 (2)
O3—C3—C4—C7	5.1 (3)	N4—N3—C16—C21	28.4 (3)
N2—C11—C13—N4	173.11 (15)	N1—C5—C6—C7	−0.3 (2)
C12—C11—C13—N4	−0.9 (2)	C10—C5—C6—C7	−179.24 (19)
N2—C11—C13—C14	−4.2 (3)	N1—C5—C6—C8	179.8 (2)
C12—C11—C13—C14	−178.26 (18)	C10—C5—C6—C8	0.8 (3)
N3—N4—C13—C11	5.04 (19)	C3—O3—C2—C1	−171.5 (2)
C15—N4—C13—C11	140.06 (17)	N1—C4—C7—C6	−0.5 (2)
N3—N4—C13—C14	−177.38 (16)	C3—C4—C7—C6	177.7 (2)
C15—N4—C13—C14	−42.4 (2)	N1—C4—C7—C9	−179.3 (2)
C4—N1—C5—C6	0.0 (2)	C3—C4—C7—C9	−1.1 (4)
C4—N1—C5—C10	179.11 (16)	C5—C6—C7—C4	0.5 (2)
N2—C10—C5—N1	−175.74 (16)	C8—C6—C7—C4	−179.6 (2)
N2—C10—C5—C6	3.1 (3)	C5—C6—C7—C9	179.3 (2)
C13—N4—N3—C12	−7.40 (19)	C8—C6—C7—C9	−0.7 (4)
C15—N4—N3—C12	−145.27 (16)	C21—C16—C17—C18	−0.1 (3)
C13—N4—N3—C16	−164.82 (15)	N3—C16—C17—C18	179.88 (19)
C15—N4—N3—C16	57.3 (2)	C16—C21—C20—C19	−0.7 (3)
N4—N3—C12—O1	−169.83 (18)	C21—C20—C19—C18	0.4 (4)
C16—N3—C12—O1	−14.0 (3)	C20—C19—C18—C17	0.1 (4)
N4—N3—C12—C11	6.73 (19)	C16—C17—C18—C19	−0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O2ⁱ	0.86	2.05	2.880 (2)	163

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄N₄O₃
M_r	380.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.421 (2), 20.141 (3), 7.5477 (13)
β (°)	96.147 (2)
V (Å³)	2028.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.21 × 0.08

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.979, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	23826, 4717, 2622
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.655

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.149, 1.01
No. of reflections	4717
No. of parameters	258
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.20

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1D···O2ⁱ	0.86	2.05	2.880 (2)	163.3

Symmetry code: (i) −x+2, −y, −z+1.

References

Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, W.-N., Wang, Y. & Wang, Q.-F. (2009). Acta Cryst. E65, o1661. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, Y., Yang, Z.-Y. & Chen, Z.-N. (2008). Bioorg. Med. Chem. Lett., 18, 298–303. Web of Science CSD CrossRef PubMed CAS Google Scholar
Yang, L. Y., Chen, Q. Q., Yang, G. Q. & Ma, J. S. (2003). Tetrahedron, 59, 10037–10041. Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1933

doi:10.1107/S1600536809027780

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 5-[(2,3-di­methyl-5-oxo-1-phenyl-2,5-di­hydro-1H-pyrazol-4-yl)imino­meth­yl]-3,4-di­methyl-1H-pyrrole-2-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

Ethyl 5-[(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)iminomethyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate