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

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

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[Wang, Y., Yang, Z.-Y. & Chen, Z.-N. (2008). Bioorg. Med. Chem. Lett., 18, 298-303.]); Yang et al. (2003[Yang, L. Y., Chen, Q. Q., Yang, G. Q. & Ma, J. S. (2003). Tetrahedron, 59, 10037-10041.]). For the structure of 5-formyl-3,4-dimethyl-1H-pyrrole-2-carb­oxyl­ate, see: Wu et al. (2009[Wu, W.-N., Wang, Y. & Wang, Q.-F. (2009). Acta Cryst. E65, o1661.]).

[Scheme 1]

Experimental

Crystal data
  • C21H24N4O3

  • Mr = 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[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.979, Tmax = 0.993

  • 23826 measured reflections

  • 4717 independent reflections

  • 2622 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.050

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

All H atoms were placed in calculated positions, with C—H = 0.93–0.97 Å and N—H = 0.86 Å, and were thereafter treated as riding, with Uiso(H) values of 1.5Ueq(C) for methyl groups and 1.2Ueq(C,N) for others.

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
[Figure 1] Fig. 1. The molecular structure shown with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. A centrosymmetric dimer via intermolecular hydrogen bonds (dashed lines)..
[Figure 3] 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
C21H24N4O3F(000) = 808
Mr = 380.44Dx = 1.246 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2702 reflections
a = 13.421 (2) Åθ = 2.5–20.3°
b = 20.141 (3) ŵ = 0.09 mm1
c = 7.5477 (13) ÅT = 296 K
β = 96.147 (2)°Block, yellow
V = 2028.5 (6) Å30.30 × 0.21 × 0.08 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
4717 independent reflections
Radiation source: fine-focus sealed tube2622 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ϕ and ω scansθmax = 27.8°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 1717
Tmin = 0.979, Tmax = 0.993k = 2626
23826 measured reflectionsl = 99
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149H-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 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C21H24N4O3V = 2028.5 (6) Å3
Mr = 380.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.421 (2) ŵ = 0.09 mm1
b = 20.141 (3) ÅT = 296 K
c = 7.5477 (13) Å0.30 × 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)
Tmin = 0.979, Tmax = 0.993Rint = 0.051
23826 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.149H-atom parameters constrained
S = 1.01Δρmax = 0.20 e Å3
4717 reflectionsΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
N10.89926 (11)0.04791 (7)0.2730 (2)0.0489 (4)
H1D0.95570.02970.30940.059*
O30.73311 (9)0.00819 (7)0.59614 (18)0.0606 (4)
O20.89663 (10)0.01469 (7)0.60113 (19)0.0637 (4)
C30.82077 (14)0.01047 (9)0.5289 (3)0.0489 (5)
N41.09462 (11)0.18926 (7)0.46225 (19)0.0497 (4)
N20.94408 (12)0.13164 (8)0.1322 (2)0.0525 (4)
C111.02102 (14)0.14408 (9)0.2378 (2)0.0475 (4)
C100.95909 (14)0.09456 (9)0.0064 (2)0.0493 (5)
H10A1.02110.07440.03410.059*
C40.81529 (13)0.04502 (9)0.3599 (3)0.0498 (5)
C131.00552 (14)0.17709 (8)0.3956 (2)0.0477 (4)
C50.88044 (13)0.08391 (9)0.1198 (2)0.0491 (5)
O11.17701 (10)0.11051 (8)0.06507 (18)0.0692 (4)
N31.16917 (11)0.15719 (8)0.3468 (2)0.0530 (4)
C121.12710 (15)0.13275 (9)0.1985 (2)0.0514 (5)
C211.30141 (16)0.23522 (10)0.4062 (3)0.0590 (5)
H211.25400.26800.43770.071*
C161.27191 (14)0.17312 (10)0.3532 (2)0.0525 (5)
C60.78108 (14)0.10470 (10)0.1085 (3)0.0548 (5)
C20.73181 (15)0.02886 (11)0.7614 (3)0.0643 (6)
H2A0.77130.00590.85770.077*
H2B0.76040.07260.74890.077*
C70.74006 (13)0.08006 (10)0.2585 (3)0.0568 (5)
C171.34292 (17)0.12484 (11)0.3051 (3)0.0674 (6)
H171.32330.08310.26930.081*
C140.90956 (15)0.20130 (10)0.4891 (3)0.0620 (5)
H14A0.89510.17760.59920.093*
H14B0.91490.24790.51340.093*
H14C0.85660.19410.41530.093*
C80.72684 (15)0.14606 (12)0.0377 (3)0.0767 (7)
H8A0.65590.14250.03280.115*
H8B0.74330.13040.15120.115*
H8C0.74680.19160.02240.115*
C151.10435 (16)0.18288 (10)0.6526 (2)0.0603 (5)
H15A1.09970.13690.68610.091*
H15B1.16810.20020.67720.091*
H15C1.05170.20740.71950.091*
C201.40162 (18)0.24783 (13)0.4116 (3)0.0772 (7)
H201.42170.28930.44850.093*
C90.63467 (16)0.09116 (14)0.3014 (4)0.0903 (9)
H9A0.62860.13530.34690.135*
H9B0.61890.05960.38950.135*
H9C0.58910.08570.19540.135*
C191.47261 (19)0.20031 (16)0.3638 (4)0.0883 (8)
H191.54030.20950.36730.106*
C181.44268 (19)0.13905 (14)0.3105 (4)0.0855 (8)
H181.49050.10670.27770.103*
C10.62731 (18)0.03477 (16)0.8013 (4)0.1050 (10)
H1A0.60350.00790.83480.157*
H1B0.62370.06550.89760.157*
H1C0.58650.05050.69760.157*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0397 (8)0.0527 (9)0.0546 (10)0.0008 (7)0.0066 (7)0.0072 (7)
O30.0435 (7)0.0775 (9)0.0624 (9)0.0040 (6)0.0131 (6)0.0224 (7)
O20.0434 (8)0.0757 (10)0.0724 (10)0.0066 (7)0.0081 (7)0.0203 (7)
C30.0405 (10)0.0491 (11)0.0578 (12)0.0047 (8)0.0087 (9)0.0025 (9)
N40.0550 (10)0.0537 (9)0.0399 (9)0.0003 (7)0.0025 (7)0.0056 (7)
N20.0564 (10)0.0528 (9)0.0482 (9)0.0069 (7)0.0058 (8)0.0030 (8)
C110.0518 (11)0.0460 (10)0.0450 (11)0.0055 (8)0.0061 (8)0.0008 (8)
C100.0479 (11)0.0499 (11)0.0500 (11)0.0051 (8)0.0048 (9)0.0004 (9)
C40.0383 (10)0.0536 (11)0.0578 (12)0.0046 (8)0.0065 (8)0.0067 (9)
C130.0542 (11)0.0418 (10)0.0463 (11)0.0030 (8)0.0018 (9)0.0016 (8)
C50.0484 (11)0.0502 (11)0.0483 (11)0.0068 (8)0.0028 (8)0.0020 (9)
O10.0629 (9)0.0895 (11)0.0536 (9)0.0007 (8)0.0006 (7)0.0250 (8)
N30.0522 (10)0.0610 (10)0.0449 (9)0.0004 (8)0.0015 (7)0.0101 (8)
C120.0590 (12)0.0524 (11)0.0425 (11)0.0035 (9)0.0048 (9)0.0066 (9)
C210.0619 (13)0.0662 (14)0.0510 (12)0.0007 (10)0.0154 (10)0.0034 (10)
C160.0536 (12)0.0608 (12)0.0435 (10)0.0006 (9)0.0078 (9)0.0018 (9)
C60.0438 (11)0.0610 (12)0.0580 (12)0.0050 (9)0.0018 (9)0.0093 (10)
C20.0563 (12)0.0795 (15)0.0589 (13)0.0055 (11)0.0142 (10)0.0197 (11)
C70.0402 (10)0.0644 (13)0.0653 (13)0.0036 (9)0.0033 (9)0.0100 (10)
C170.0686 (15)0.0661 (14)0.0673 (15)0.0066 (11)0.0061 (11)0.0011 (11)
C140.0622 (13)0.0608 (12)0.0610 (13)0.0004 (10)0.0020 (10)0.0048 (10)
C80.0532 (13)0.0964 (18)0.0782 (16)0.0009 (12)0.0035 (11)0.0289 (14)
C150.0747 (14)0.0643 (13)0.0417 (11)0.0035 (11)0.0049 (10)0.0040 (10)
C200.0709 (16)0.0917 (17)0.0721 (16)0.0158 (14)0.0214 (12)0.0067 (13)
C90.0450 (13)0.122 (2)0.105 (2)0.0141 (13)0.0165 (13)0.0387 (17)
C190.0566 (15)0.120 (2)0.0905 (19)0.0054 (16)0.0181 (13)0.0016 (17)
C180.0608 (16)0.104 (2)0.0924 (19)0.0211 (14)0.0100 (13)0.0017 (16)
C10.0648 (16)0.146 (3)0.108 (2)0.0029 (16)0.0275 (15)0.0547 (19)
Geometric parameters (Å, º) top
N1—C41.364 (2)C6—C81.507 (3)
N1—C51.366 (2)C2—C11.471 (3)
N1—H1D0.8600C2—H2A0.9700
O3—C31.331 (2)C2—H2B0.9700
O3—C21.455 (2)C7—C91.501 (3)
O2—C31.213 (2)C17—C181.374 (3)
C3—C41.448 (3)C17—H170.9300
N4—C131.368 (2)C14—H14A0.9600
N4—N31.411 (2)C14—H14B0.9600
N4—C151.462 (2)C14—H14C0.9600
N2—C101.284 (2)C8—H8A0.9600
N2—C111.393 (2)C8—H8B0.9600
C11—C131.361 (2)C8—H8C0.9600
C11—C121.441 (3)C15—H15A0.9600
C10—C51.444 (3)C15—H15B0.9600
C10—H10A0.9300C15—H15C0.9600
C4—C71.392 (3)C20—C191.371 (3)
C13—C141.483 (3)C20—H200.9300
C5—C61.392 (3)C9—H9A0.9600
O1—C121.233 (2)C9—H9B0.9600
N3—C121.396 (2)C9—H9C0.9600
N3—C161.422 (2)C19—C181.371 (4)
C21—C201.374 (3)C19—H190.9300
C21—C161.384 (3)C18—H180.9300
C21—H210.9300C1—H1A0.9600
C16—C171.383 (3)C1—H1B0.9600
C6—C71.402 (3)C1—H1C0.9600
C4—N1—C5110.02 (15)H2A—C2—H2B108.4
C4—N1—H1D125.0C4—C7—C6107.40 (16)
C5—N1—H1D125.0C4—C7—C9126.99 (18)
C3—O3—C2115.88 (15)C6—C7—C9125.61 (18)
O2—C3—O3123.23 (18)C18—C17—C16119.5 (2)
O2—C3—C4123.89 (17)C18—C17—H17120.3
O3—C3—C4112.88 (16)C16—C17—H17120.3
C13—N4—N3106.31 (14)C13—C14—H14A109.5
C13—N4—C15121.26 (15)C13—C14—H14B109.5
N3—N4—C15115.75 (15)H14A—C14—H14B109.5
C10—N2—C11120.64 (17)C13—C14—H14C109.5
C13—C11—N2122.38 (17)H14A—C14—H14C109.5
C13—C11—C12108.20 (16)H14B—C14—H14C109.5
N2—C11—C12129.10 (16)C6—C8—H8A109.5
N2—C10—C5120.56 (18)C6—C8—H8B109.5
N2—C10—H10A119.7H8A—C8—H8B109.5
C5—C10—H10A119.7C6—C8—H8C109.5
N1—C4—C7107.58 (16)H8A—C8—H8C109.5
N1—C4—C3118.50 (16)H8B—C8—H8C109.5
C7—C4—C3133.90 (17)N4—C15—H15A109.5
C11—C13—N4110.59 (16)N4—C15—H15B109.5
C11—C13—C14128.38 (18)H15A—C15—H15B109.5
N4—C13—C14120.98 (16)N4—C15—H15C109.5
N1—C5—C6107.48 (16)H15A—C15—H15C109.5
N1—C5—C10120.00 (16)H15B—C15—H15C109.5
C6—C5—C10132.51 (18)C21—C20—C19121.2 (2)
C12—N3—N4109.60 (15)C21—C20—H20119.4
C12—N3—C16125.72 (15)C19—C20—H20119.4
N4—N3—C16120.13 (15)C7—C9—H9A109.5
O1—C12—N3123.51 (18)C7—C9—H9B109.5
O1—C12—C11131.60 (17)H9A—C9—H9B109.5
N3—C12—C11104.78 (15)C7—C9—H9C109.5
C20—C21—C16119.1 (2)H9A—C9—H9C109.5
C20—C21—H21120.4H9B—C9—H9C109.5
C16—C21—H21120.4C18—C19—C20119.2 (2)
C17—C16—C21120.1 (2)C18—C19—H19120.4
C17—C16—N3118.44 (18)C20—C19—H19120.4
C21—C16—N3121.49 (18)C19—C18—C17120.9 (2)
C5—C6—C7107.52 (16)C19—C18—H18119.6
C5—C6—C8126.55 (18)C17—C18—H18119.6
C7—C6—C8125.93 (18)C2—C1—H1A109.5
O3—C2—C1108.44 (17)C2—C1—H1B109.5
O3—C2—H2A110.0H1A—C1—H1B109.5
C1—C2—H2A110.0C2—C1—H1C109.5
O3—C2—H2B110.0H1A—C1—H1C109.5
C1—C2—H2B110.0H1B—C1—H1C109.5
C2—O3—C3—O22.1 (3)C16—N3—C12—C11162.58 (17)
C2—O3—C3—C4176.86 (16)C13—C11—C12—O1172.6 (2)
C10—N2—C11—C13172.78 (17)N2—C11—C12—O10.9 (3)
C10—N2—C11—C1214.5 (3)C13—C11—C12—N33.6 (2)
C11—N2—C10—C5177.46 (16)N2—C11—C12—N3177.11 (17)
C5—N1—C4—C70.3 (2)C20—C21—C16—C170.6 (3)
C5—N1—C4—C3178.24 (16)C20—C21—C16—N3179.38 (18)
O2—C3—C4—N12.1 (3)C12—N3—C16—C1754.9 (3)
O3—C3—C4—N1176.84 (16)N4—N3—C16—C17151.52 (18)
O2—C3—C4—C7175.9 (2)C12—N3—C16—C21125.1 (2)
O3—C3—C4—C75.1 (3)N4—N3—C16—C2128.4 (3)
N2—C11—C13—N4173.11 (15)N1—C5—C6—C70.3 (2)
C12—C11—C13—N40.9 (2)C10—C5—C6—C7179.24 (19)
N2—C11—C13—C144.2 (3)N1—C5—C6—C8179.8 (2)
C12—C11—C13—C14178.26 (18)C10—C5—C6—C80.8 (3)
N3—N4—C13—C115.04 (19)C3—O3—C2—C1171.5 (2)
C15—N4—C13—C11140.06 (17)N1—C4—C7—C60.5 (2)
N3—N4—C13—C14177.38 (16)C3—C4—C7—C6177.7 (2)
C15—N4—C13—C1442.4 (2)N1—C4—C7—C9179.3 (2)
C4—N1—C5—C60.0 (2)C3—C4—C7—C91.1 (4)
C4—N1—C5—C10179.11 (16)C5—C6—C7—C40.5 (2)
N2—C10—C5—N1175.74 (16)C8—C6—C7—C4179.6 (2)
N2—C10—C5—C63.1 (3)C5—C6—C7—C9179.3 (2)
C13—N4—N3—C127.40 (19)C8—C6—C7—C90.7 (4)
C15—N4—N3—C12145.27 (16)C21—C16—C17—C180.1 (3)
C13—N4—N3—C16164.82 (15)N3—C16—C17—C18179.88 (19)
C15—N4—N3—C1657.3 (2)C16—C21—C20—C190.7 (3)
N4—N3—C12—O1169.83 (18)C21—C20—C19—C180.4 (4)
C16—N3—C12—O114.0 (3)C20—C19—C18—C170.1 (4)
N4—N3—C12—C116.73 (19)C16—C17—C18—C190.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1D···O2i0.862.052.880 (2)163
Symmetry code: (i) x+2, y, z+1.

Experimental details

Crystal data
Chemical formulaC21H24N4O3
Mr380.44
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)13.421 (2), 20.141 (3), 7.5477 (13)
β (°) 96.147 (2)
V3)2028.5 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.21 × 0.08
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.979, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
23826, 4717, 2622
Rint0.051
(sin θ/λ)max1)0.655
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.149, 1.01
No. of reflections4717
No. of parameters258
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H1D···O2i0.862.052.880 (2)163.3
Symmetry code: (i) x+2, y, z+1.
 

References

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

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