Ethyl 5-[(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)imino-meth-yl]-3,4-dimethyl-1H-pyrrole-2-carboxyl-ate.

In the title compound, C(21)H(24)N(4)O(3), the mol-ecule has an E configuration about the imine C=N double bond. Inter-molecular N-H⋯O hydrogen bonds assemble mol-ecules 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 = 380.44

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.149

S = 1.01

4717 reflections

258 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.20 e Å−3

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.

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

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

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

C21H24N4O3	F(000) = 808
Mr = 380.44	Dx = 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

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

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(Fo2) + (0.07P)2 + 0.1292P] where P = (Fo2 + 2Fc2)/3
4717 reflections	(Δ/σ)max < 0.001
258 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.20 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
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*

	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)

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)

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

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) .