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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

[6-(Furan-2-yl)-7-nitro-2,3,4,6,7,8-hexa­hydro-1H-pyrido[1,2-a]pyrimidin-9-yl](phen­yl)methanone

aCollege of Chemistry and Chemical Engineering, Jiang Xi Normal University, Nanchang, Jiang Xi 330022, People's Republic of China, and bBeijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China
*Correspondence e-mail: yucy@iccas.ac.cn

(Received 16 March 2013; accepted 20 May 2013; online 31 May 2013)

The asymmetric unit of the title compound, C19H19N3O4, contains two mol­ecules with very few conformational differences; a C atom in the pyrimidine ring in one of the mol­ecules is disordered in a 0.688 (15):0.312 (15) ratio. In both mol­ecules, the fused pyridine and pyrimidine rings adopt half-chair conformations. The dihedral angles between the furan and benzene rings are 81.00 (13) and 84.99 (10)° in the two mol­ecules. The mol­ecular structure is consolidated by intra­molecular N—H⋯O hydrogen bonding. In the crystal, C—H⋯O hydrogen bonds connect the molecules into a three-dimensional network.

Related literature

For background to heterocyclic ketene aminals, see: Yaqub et al. (2008[Yaqub, M., Yu, C.-Y., Jia, Y.-M. & Huang, Z.-T. (2008). Synlett, 9, 1357-1360.]); Huang & Wang (1994[Huang, Z.-T. & Wang, M.-X. (1994). Heterocycles, 37, 1233-1262.]); Yu et al. (2006[Yu, C.-Y., Yang, P.-H., Zhao, M.-X. & Huang, Z.-T. (2006). Synlett, pp. 1835-1840.]); For the crystal structure of a related compound, see: Yu et al. (2007[Yu, C.-Y., Yuan, X.-N. & Huang, Z.-T. (2007). Acta Cryst. E63, o3186.]).

[Scheme 1]

Experimental

Crystal data
  • C19H19N3O4

  • Mr = 353.37

  • Monoclinic, P 21 /c

  • a = 13.506 (3) Å

  • b = 17.675 (4) Å

  • c = 14.755 (3) Å

  • β = 105.12 (3)°

  • V = 3400.3 (12) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 173 K

  • 0.44 × 0.43 × 0.37 mm

Data collection
  • Rigaku R-AXIS RAPID IP area-detector diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.958, Tmax = 0.964

  • 11765 measured reflections

  • 5990 independent reflections

  • 4405 reflections with I > 2σ(I)

  • Rint = 0.024

Refinement
  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.126

  • S = 1.02

  • 5990 reflections

  • 479 parameters

  • 40 restraints

  • H-atom parameters constrained

  • Δρmax = 0.59 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1A—H1AA⋯O1A 0.88 1.84 2.553 (2) 137
N1B—H1BA⋯O1B 0.88 1.85 2.556 (3) 136
C6A—H6AA⋯O1B 1.00 2.36 3.103 (3) 130
C7A—H7AB⋯O2A 0.99 2.44 2.790 (3) 100

Data collection: RAPID-AUTO (Rigaku, 2001[Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: SHELX97.

Supporting information


Comment top

Heterocyclic ketene aminals (HKAs), by high caliber of distinctive electronic feature, have been widely used as flexible synthons for the construction of a variety of fused-ring polycyclic heterocycles (Huang & Wang, 1994; Yu et al., 2006; Yaqub et al., 2008) and therefore highly noteworthy in contemporary organic synthesis.

The asymmetric unit of the title compound, is composed of two molecules with very little conformational differences; a C-atom in the pyrimidine ring in one of the molecules is disordered in 0.688 (15):0.312 (15) ratio. The bond distances and angles in both molecules of the title compound (Fig. 1) agree very well with the corresponding bond distances and angles reported in a closely related compound (Yu et al., 2007). The fused pyridyl (N2A/C4A—C8A), (N2B/C4B—C8B) and pyrimidyl (N1A/N2A/C1A—C3A/C4A), (N1B/N2BC1B—C3B/C4B) rings adopt half-chair conformations. The atoms C2A, C6A, C6B, C2B and C2D lie 0.647 (4), 0.611 (3), 0.614 (3), -0.295 (10) and 0.523 (10) Å, respectively, out of the planes formed by the remaining ring atoms. The molecular packing in the crystal structure is consolidated by intermolecular C—H···O hydrogen bonding (Table 1 & Fig. 2).

Related literature top

For background to heterocyclic ketene aminals, see: Yaqub et al. (2008); Huang & Wang (1994); Yu et al. (2006); For thecrystal structure of a related compound, see: Yu et al. (2007).

Experimental top

(E)-3-(furan-2-yl)-2-nitroallyl acetate (211 mg, 1 mmol) and 1-phenyl-2- (tetrahydropyrimidin-2(1H)-ylidene)ethanone (202 mg, 1 mmol) were stirred in 20 ml of dichloromethane at 273 K for 1 h. Then the temperature was allowed to rise up to the room temperature and stirred for another 6 h. The solvent was removed in vacuo and the residue was purified by flash column chromatography (silica gel, petroleum ether/EtOAc 1:1) to give the title compound as a light yellow solid. The single crystals of the title compound were grown in dichloromethane - petroleum ether (1:5) system at room temperature by slow evaporation. Yield: 75% (264.8 mg), m.p. 457–458 K.

Refinement top

All H atoms were positioned geometrically and refined using a riding model with distances C—H = 0.95, 0.99 or 1.00 Å for aryl, methylene and methine H-atoms, respectively, and N—H = 0.88 Å. The H-atoms are constrained to ride on their parent atoms, with Uiso(H) = 1.2 times Ueq(C/N). The atom C2B and C2D of molecule B are disordered with sire occupancy factors 0.688 (15) and 0.312 (15), respectively; the commands ISOR and SADI were used to model the disorder.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); 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: SHELX97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing both molecules in the asymmetric unit. Displacement ellipsoids are drawn at the 30% probability level and the smaller fraction (C2D) of the disordered atom has been ignored.
[Figure 2] Fig. 2. The crystal packing for title compound, with intramolecular hydrogen bonding N—H···O and intermolecular C—H···O hydrogen bonding interactions shown as dashed lines.
[6-(Furan-2-yl)-7-nitro-2,3,4,6,7,8-hexahydro-1H-pyrido[1,2-a]pyrimidin-9-yl](phenyl)methanone top
Crystal data top
C19H19N3O4F(000) = 1488
Mr = 353.37Dx = 1.381 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 55355 reflections
a = 13.506 (3) Åθ = 2.2–27.5°
b = 17.675 (4) ŵ = 0.10 mm1
c = 14.755 (3) ÅT = 173 K
β = 105.12 (3)°Block, yellow
V = 3400.3 (12) Å30.44 × 0.43 × 0.37 mm
Z = 8
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
5990 independent reflections
Radiation source: rotating anode4405 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω scans at fixed χ = 45°θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1616
Tmin = 0.958, Tmax = 0.964k = 2021
11765 measured reflectionsl = 1717
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0698P)2]
where P = (Fo2 + 2Fc2)/3
5990 reflections(Δ/σ)max < 0.001
479 parametersΔρmax = 0.59 e Å3
40 restraintsΔρmin = 0.26 e Å3
Crystal data top
C19H19N3O4V = 3400.3 (12) Å3
Mr = 353.37Z = 8
Monoclinic, P21/cMo Kα radiation
a = 13.506 (3) ŵ = 0.10 mm1
b = 17.675 (4) ÅT = 173 K
c = 14.755 (3) Å0.44 × 0.43 × 0.37 mm
β = 105.12 (3)°
Data collection top
Rigaku R-AXIS RAPID IP area-detector
diffractometer
5990 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
4405 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.964Rint = 0.024
11765 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04940 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.02Δρmax = 0.59 e Å3
5990 reflectionsΔρmin = 0.26 e Å3
479 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*/UeqOcc. (<1)
O1A0.55143 (11)0.64789 (9)0.96144 (10)0.0292 (4)
O1B0.20201 (12)0.49311 (9)0.48209 (10)0.0348 (4)
O2A0.26198 (16)0.64416 (12)0.65380 (14)0.0602 (6)
O2B0.04702 (15)0.49215 (12)0.10899 (13)0.0542 (5)
O3A0.36728 (16)0.63894 (12)0.56801 (15)0.0619 (6)
O3B0.00216 (17)0.38763 (12)0.16041 (15)0.0612 (6)
O4B0.24369 (11)0.62772 (9)0.13117 (10)0.0287 (4)
N1A0.63716 (13)0.62164 (11)0.82954 (13)0.0298 (4)
H1AA0.63540.64580.88130.036*
N1B0.17129 (14)0.60783 (11)0.37285 (13)0.0324 (5)
H1BA0.20530.58630.42560.039*
N2A0.54886 (13)0.55555 (11)0.69830 (12)0.0277 (4)
N2B0.02541 (14)0.61336 (11)0.25015 (12)0.0322 (5)
N3B0.00221 (15)0.45606 (13)0.15228 (13)0.0373 (5)
N3A0.32970 (16)0.61309 (12)0.62734 (13)0.0359 (5)
C1A0.73214 (18)0.62515 (15)0.80068 (18)0.0383 (6)
H1AB0.79150.62050.85630.046*
H1AC0.73700.67440.77030.046*
C1B0.2157 (2)0.67467 (16)0.3425 (2)0.0496 (7)
H1B10.22120.71440.39080.060*
H1B20.28620.66220.33940.060*
C3B0.0542 (2)0.68725 (16)0.2204 (2)0.0514 (8)
H3B10.03640.68880.15090.062*
H3B20.01360.72690.24170.062*
C2B0.1630 (9)0.7045 (8)0.2566 (8)0.052 (4)0.312 (15)
H2B10.19830.68740.20930.063*0.312 (15)
H2B20.17000.76020.26090.063*0.312 (15)
C2D0.1329 (4)0.7263 (3)0.2906 (4)0.0385 (15)0.688 (15)
H2DA0.10080.75120.33600.046*0.688 (15)
H2DB0.16350.76630.25950.046*0.688 (15)
C2A0.73418 (19)0.56157 (17)0.73265 (18)0.0451 (7)
H2AA0.79220.56910.70420.054*
H2AB0.74430.51270.76660.054*
C3A0.63701 (18)0.55976 (17)0.65830 (17)0.0416 (6)
H3AA0.63150.60590.61920.050*
H3AB0.63670.51530.61730.050*
C4A0.55271 (16)0.58496 (12)0.78425 (14)0.0234 (5)
C4B0.08267 (16)0.57667 (13)0.32670 (14)0.0251 (5)
C5A0.46227 (17)0.51183 (13)0.64412 (14)0.0287 (5)
H5AA0.45450.52320.57620.034*
C5B0.06863 (16)0.58213 (14)0.18796 (14)0.0299 (5)
H5BA0.06840.59330.12160.036*
C6A0.36290 (16)0.53476 (13)0.66721 (14)0.0268 (5)
H6AA0.30830.49760.63720.032*
C6B0.07479 (16)0.49688 (13)0.19890 (14)0.0283 (5)
H6BA0.14640.48040.16770.034*
C7B0.05028 (16)0.47362 (13)0.30167 (14)0.0273 (5)
H7BA0.10520.49190.32940.033*
H7BB0.04820.41770.30620.033*
C7A0.37489 (16)0.53393 (13)0.77222 (14)0.0263 (5)
H7AA0.38040.48090.79460.032*
H7AB0.31300.55630.78550.032*
C8A0.46871 (15)0.57758 (12)0.82560 (13)0.0222 (5)
C8B0.05145 (16)0.50557 (12)0.35655 (14)0.0242 (5)
C9A0.47556 (16)0.60980 (12)0.91401 (14)0.0229 (5)
C9B0.11666 (16)0.46693 (13)0.43265 (14)0.0254 (5)
C10A0.38851 (16)0.60200 (12)0.95995 (13)0.0230 (5)
C10B0.09194 (16)0.38818 (13)0.45760 (13)0.0259 (5)
C11A0.34535 (17)0.53268 (13)0.97289 (14)0.0276 (5)
H11A0.36960.48760.95090.033*
C11B0.00181 (17)0.36644 (14)0.47148 (14)0.0296 (5)
H11B0.05610.40210.46250.036*
C12B0.0166 (2)0.29339 (15)0.49820 (15)0.0373 (6)
H12A0.08080.27920.50800.045*
C12A0.26713 (18)0.52905 (15)1.01778 (15)0.0344 (6)
H12B0.23790.48151.02630.041*
C13A0.23158 (18)0.59423 (16)1.05003 (16)0.0389 (6)
H13A0.17670.59171.07910.047*
C13B0.0618 (2)0.24065 (15)0.51081 (15)0.0407 (6)
H13B0.05100.19030.52860.049*
C14A0.27549 (19)0.66288 (15)1.04015 (16)0.0374 (6)
H14A0.25190.70761.06350.045*
C14B0.1552 (2)0.26133 (14)0.49747 (15)0.0374 (6)
H14B0.20900.22530.50590.045*
C15A0.35421 (17)0.66683 (13)0.99604 (15)0.0297 (5)
H15A0.38510.71430.99040.036*
C15B0.17047 (18)0.33420 (14)0.47193 (14)0.0326 (6)
H15B0.23550.34830.46380.039*
C16B0.16076 (16)0.61908 (13)0.20724 (14)0.0283 (5)
C16A0.48366 (18)0.42951 (14)0.65825 (17)0.0361 (6)
C17B0.18188 (19)0.64543 (15)0.28504 (16)0.0383 (6)
H17A0.13720.64600.34660.046*
C18B0.28476 (18)0.67257 (14)0.25721 (16)0.0349 (6)
H18A0.32200.69480.29680.042*
C19B0.31867 (17)0.66084 (13)0.16511 (16)0.0306 (5)
H19A0.38530.67360.12820.037*
C17A0.5364 (2)0.38770 (16)0.7306 (2)0.0510 (7)
H17B0.57080.40480.79170.061*
C18A0.5296 (3)0.31100 (17)0.6957 (3)0.0708 (10)
H18B0.55920.26740.72980.085*
C19A0.4745 (3)0.31298 (19)0.6076 (3)0.0704 (10)
H19B0.45780.27000.56780.085*
O4A0.44496 (14)0.38476 (11)0.58157 (13)0.0528 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0272 (8)0.0292 (9)0.0296 (8)0.0041 (7)0.0045 (7)0.0069 (7)
O1B0.0290 (9)0.0367 (10)0.0320 (8)0.0037 (7)0.0038 (7)0.0021 (7)
O2A0.0616 (13)0.0578 (14)0.0649 (13)0.0333 (11)0.0232 (11)0.0109 (10)
O2B0.0504 (12)0.0714 (14)0.0510 (11)0.0082 (10)0.0315 (10)0.0077 (10)
O3A0.0639 (13)0.0571 (14)0.0707 (13)0.0140 (11)0.0282 (11)0.0324 (11)
O3B0.0762 (15)0.0410 (13)0.0757 (14)0.0046 (11)0.0363 (12)0.0140 (11)
O4B0.0270 (8)0.0316 (9)0.0241 (7)0.0015 (7)0.0007 (6)0.0006 (7)
N1A0.0256 (10)0.0307 (11)0.0349 (10)0.0038 (9)0.0113 (8)0.0101 (9)
N1B0.0257 (10)0.0325 (11)0.0351 (10)0.0060 (9)0.0011 (8)0.0024 (9)
N2A0.0262 (10)0.0343 (11)0.0245 (9)0.0009 (8)0.0102 (8)0.0028 (8)
N2B0.0281 (10)0.0340 (12)0.0314 (10)0.0050 (9)0.0020 (8)0.0080 (9)
N3B0.0303 (11)0.0486 (15)0.0300 (11)0.0036 (10)0.0026 (9)0.0072 (10)
N3A0.0348 (11)0.0368 (12)0.0326 (10)0.0032 (10)0.0023 (9)0.0030 (9)
C1A0.0286 (13)0.0381 (15)0.0529 (15)0.0066 (11)0.0189 (11)0.0051 (12)
C1B0.0331 (15)0.0450 (17)0.0668 (19)0.0107 (13)0.0059 (13)0.0096 (14)
C3B0.0450 (17)0.0434 (18)0.0596 (17)0.0068 (14)0.0028 (14)0.0196 (14)
C2B0.071 (7)0.055 (7)0.036 (5)0.028 (5)0.023 (5)0.002 (5)
C2D0.046 (3)0.035 (2)0.035 (3)0.0075 (19)0.0113 (19)0.0070 (18)
C2A0.0358 (14)0.0585 (18)0.0459 (15)0.0001 (13)0.0196 (12)0.0038 (13)
C3A0.0356 (14)0.0571 (18)0.0384 (13)0.0031 (13)0.0210 (11)0.0027 (12)
C4A0.0235 (11)0.0191 (11)0.0267 (11)0.0025 (9)0.0052 (9)0.0002 (9)
C4B0.0213 (11)0.0312 (13)0.0232 (10)0.0022 (10)0.0062 (9)0.0005 (9)
C5A0.0307 (12)0.0342 (14)0.0209 (10)0.0016 (10)0.0060 (9)0.0029 (9)
C5B0.0258 (12)0.0405 (15)0.0209 (10)0.0006 (11)0.0019 (9)0.0043 (10)
C6A0.0256 (11)0.0271 (13)0.0260 (11)0.0011 (10)0.0036 (9)0.0023 (9)
C6B0.0202 (11)0.0378 (14)0.0248 (11)0.0030 (10)0.0024 (9)0.0013 (10)
C7B0.0244 (11)0.0297 (13)0.0273 (11)0.0004 (10)0.0057 (9)0.0000 (9)
C7A0.0262 (12)0.0284 (13)0.0248 (11)0.0020 (10)0.0076 (9)0.0025 (9)
C8A0.0219 (11)0.0216 (11)0.0233 (10)0.0026 (9)0.0060 (9)0.0004 (9)
C8B0.0228 (11)0.0270 (12)0.0220 (10)0.0006 (9)0.0047 (9)0.0025 (9)
C9A0.0242 (11)0.0182 (11)0.0248 (10)0.0035 (9)0.0035 (9)0.0022 (9)
C9B0.0248 (12)0.0294 (13)0.0217 (10)0.0008 (10)0.0055 (9)0.0037 (9)
C10A0.0250 (11)0.0235 (12)0.0185 (10)0.0022 (9)0.0023 (9)0.0017 (8)
C10B0.0283 (12)0.0318 (13)0.0171 (10)0.0001 (10)0.0048 (9)0.0023 (9)
C11A0.0340 (13)0.0257 (13)0.0225 (10)0.0009 (10)0.0061 (9)0.0002 (9)
C11B0.0309 (12)0.0363 (14)0.0215 (11)0.0003 (10)0.0064 (9)0.0006 (9)
C12B0.0423 (15)0.0474 (17)0.0230 (11)0.0141 (13)0.0100 (11)0.0005 (11)
C12A0.0386 (14)0.0383 (15)0.0266 (11)0.0087 (12)0.0091 (10)0.0033 (10)
C13A0.0338 (14)0.0543 (18)0.0332 (13)0.0001 (12)0.0174 (11)0.0029 (12)
C13B0.0623 (18)0.0315 (15)0.0256 (12)0.0072 (13)0.0069 (12)0.0028 (10)
C14A0.0400 (14)0.0393 (15)0.0373 (13)0.0111 (12)0.0178 (11)0.0010 (11)
C14B0.0503 (16)0.0336 (15)0.0273 (12)0.0080 (12)0.0083 (11)0.0014 (10)
C15A0.0354 (13)0.0236 (12)0.0302 (11)0.0044 (10)0.0087 (10)0.0029 (10)
C15B0.0333 (13)0.0396 (15)0.0255 (11)0.0063 (11)0.0087 (10)0.0036 (10)
C16B0.0264 (12)0.0308 (13)0.0246 (11)0.0019 (10)0.0009 (9)0.0023 (9)
C16A0.0296 (13)0.0353 (15)0.0448 (14)0.0008 (11)0.0121 (11)0.0086 (12)
C17B0.0367 (14)0.0499 (17)0.0244 (12)0.0010 (12)0.0008 (10)0.0051 (11)
C18B0.0345 (14)0.0344 (14)0.0365 (13)0.0008 (11)0.0106 (11)0.0066 (11)
C19B0.0230 (12)0.0299 (13)0.0368 (12)0.0020 (10)0.0043 (10)0.0004 (10)
C17A0.0348 (14)0.0386 (17)0.078 (2)0.0049 (13)0.0114 (14)0.0096 (14)
C18A0.0468 (19)0.0324 (18)0.145 (3)0.0115 (14)0.047 (2)0.014 (2)
C19A0.057 (2)0.041 (2)0.127 (3)0.0036 (16)0.049 (2)0.027 (2)
O4A0.0515 (12)0.0452 (13)0.0658 (12)0.0053 (10)0.0224 (10)0.0292 (10)
Geometric parameters (Å, º) top
O1A—C9A1.272 (2)C6A—C7A1.515 (3)
O1B—C9B1.279 (3)C6A—H6AA1.0000
O2A—N3A1.215 (3)C6B—C7B1.522 (3)
O2B—N3B1.216 (3)C6B—H6BA1.0000
O3A—N3A1.210 (3)C7B—C8B1.511 (3)
O3B—N3B1.215 (3)C7B—H7BA0.9900
O4B—C16B1.372 (2)C7B—H7BB0.9900
O4B—C19B1.372 (3)C7A—C8A1.517 (3)
N1A—C4A1.331 (3)C7A—H7AA0.9900
N1A—C1A1.455 (3)C7A—H7AB0.9900
N1A—H1AA0.8800C8A—C9A1.404 (3)
N1B—C4B1.332 (3)C8B—C9B1.410 (3)
N1B—C1B1.448 (3)C9A—C10A1.509 (3)
N1B—H1BA0.8800C9B—C10B1.499 (3)
N2A—C4A1.359 (3)C10A—C11A1.391 (3)
N2A—C5A1.455 (3)C10A—C15A1.393 (3)
N2A—C3A1.462 (3)C10B—C11B1.389 (3)
N2B—C4B1.356 (3)C10B—C15B1.401 (3)
N2B—C3B1.463 (3)C11A—C12A1.387 (3)
N2B—C5B1.467 (3)C11A—H11A0.9500
N3B—C6B1.519 (3)C11B—C12B1.379 (3)
N3A—C6A1.525 (3)C11B—H11B0.9500
C1A—C2A1.512 (4)C12B—C13B1.386 (4)
C1A—H1AB0.9900C12B—H12A0.9500
C1A—H1AC0.9900C12A—C13A1.380 (4)
C1B—C2B1.385 (8)C12A—H12B0.9500
C1B—C2D1.492 (5)C13A—C14A1.375 (4)
C1B—H1B10.9900C13A—H13A0.9500
C1B—H1B20.9900C13B—C14B1.376 (4)
C3B—C2D1.451 (5)C13B—H13B0.9500
C3B—C2B1.458 (10)C14A—C15A1.385 (3)
C3B—H3B10.9900C14A—H14A0.9500
C3B—H3B20.9900C14B—C15B1.373 (3)
C2B—H2B10.9900C14B—H14B0.9500
C2B—H2B20.9900C15A—H15A0.9500
C2D—H2DA0.9900C15B—H15B0.9500
C2D—H2DB0.9900C16B—C17B1.337 (3)
C2A—C3A1.475 (4)C16A—C17A1.340 (4)
C2A—H2AA0.9900C16A—O4A1.368 (3)
C2A—H2AB0.9900C17B—C18B1.425 (3)
C3A—H3AA0.9900C17B—H17A0.9500
C3A—H3AB0.9900C18B—C19B1.332 (3)
C4A—C8A1.427 (3)C18B—H18A0.9500
C4B—C8B1.431 (3)C19B—H19A0.9500
C5A—C16A1.487 (3)C17A—C18A1.445 (4)
C5A—C6A1.523 (3)C17A—H17B0.9500
C5A—H5AA1.0000C18A—C19A1.320 (5)
C5B—C16B1.497 (3)C18A—H18B0.9500
C5B—C6B1.520 (3)C19A—O4A1.355 (4)
C5B—H5BA1.0000C19A—H19B0.9500
C16B—O4B—C19B105.76 (16)N3B—C6B—C5B111.30 (19)
C4A—N1A—C1A125.44 (19)N3B—C6B—C7B108.94 (18)
C4A—N1A—H1AA117.3C5B—C6B—C7B111.72 (18)
C1A—N1A—H1AA117.3N3B—C6B—H6BA108.3
C4B—N1B—C1B124.6 (2)C5B—C6B—H6BA108.3
C4B—N1B—H1BA117.7C7B—C6B—H6BA108.3
C1B—N1B—H1BA117.7C8B—C7B—C6B111.35 (18)
C4A—N2A—C5A123.06 (18)C8B—C7B—H7BA109.4
C4A—N2A—C3A121.35 (19)C6B—C7B—H7BA109.4
C5A—N2A—C3A115.33 (17)C8B—C7B—H7BB109.4
C4B—N2B—C3B122.60 (19)C6B—C7B—H7BB109.4
C4B—N2B—C5B123.62 (19)H7BA—C7B—H7BB108.0
C3B—N2B—C5B113.75 (18)C6A—C7A—C8A112.21 (18)
O3B—N3B—O2B123.7 (2)C6A—C7A—H7AA109.2
O3B—N3B—C6B116.7 (2)C8A—C7A—H7AA109.2
O2B—N3B—C6B119.7 (2)C6A—C7A—H7AB109.2
O3A—N3A—O2A123.7 (2)C8A—C7A—H7AB109.2
O3A—N3A—C6A119.0 (2)H7AA—C7A—H7AB107.9
O2A—N3A—C6A117.2 (2)C9A—C8A—C4A119.54 (19)
N1A—C1A—C2A109.4 (2)C9A—C8A—C7A122.16 (18)
N1A—C1A—H1AB109.8C4A—C8A—C7A118.30 (17)
C2A—C1A—H1AB109.8C9B—C8B—C4B119.84 (19)
N1A—C1A—H1AC109.8C9B—C8B—C7B122.5 (2)
C2A—C1A—H1AC109.8C4B—C8B—C7B117.59 (18)
H1AB—C1A—H1AC108.2O1A—C9A—C8A125.0 (2)
C2B—C1B—N1B116.0 (4)O1A—C9A—C10A114.30 (17)
N1B—C1B—C2D110.0 (3)C8A—C9A—C10A120.67 (18)
C2B—C1B—H1B1108.3O1B—C9B—C8B124.2 (2)
N1B—C1B—H1B1108.3O1B—C9B—C10B114.91 (18)
C2D—C1B—H1B180.9C8B—C9B—C10B120.82 (19)
C2B—C1B—H1B2108.3C11A—C10A—C15A118.6 (2)
N1B—C1B—H1B2108.3C11A—C10A—C9A123.07 (19)
C2D—C1B—H1B2135.6C15A—C10A—C9A118.2 (2)
H1B1—C1B—H1B2107.4C11B—C10B—C15B118.2 (2)
C2D—C3B—N2B114.4 (3)C11B—C10B—C9B124.3 (2)
C2B—C3B—N2B113.4 (5)C15B—C10B—C9B117.4 (2)
C2D—C3B—H3B1131.4C12A—C11A—C10A120.3 (2)
C2B—C3B—H3B1108.9C12A—C11A—H11A119.8
N2B—C3B—H3B1108.9C10A—C11A—H11A119.8
C2D—C3B—H3B278.4C12B—C11B—C10B120.4 (2)
C2B—C3B—H3B2108.9C12B—C11B—H11B119.8
N2B—C3B—H3B2108.9C10B—C11B—H11B119.8
H3B1—C3B—H3B2107.7C11B—C12B—C13B120.4 (2)
C1B—C2B—C3B119.0 (7)C11B—C12B—H12A119.8
C1B—C2B—H2B1107.6C13B—C12B—H12A119.8
C3B—C2B—H2B1107.6C13A—C12A—C11A120.2 (2)
C1B—C2B—H2B2107.6C13A—C12A—H12B119.9
C3B—C2B—H2B2107.6C11A—C12A—H12B119.9
H2B1—C2B—H2B2107.0C14A—C13A—C12A120.1 (2)
C3B—C2D—C1B112.7 (4)C14A—C13A—H13A119.9
C3B—C2D—H2DA109.0C12A—C13A—H13A119.9
C1B—C2D—H2DA109.0C14B—C13B—C12B119.9 (2)
C3B—C2D—H2DB109.0C14B—C13B—H13B120.0
C1B—C2D—H2DB109.0C12B—C13B—H13B120.0
H2DA—C2D—H2DB107.8C13A—C14A—C15A120.0 (2)
C3A—C2A—C1A110.1 (2)C13A—C14A—H14A120.0
C3A—C2A—H2AA109.6C15A—C14A—H14A120.0
C1A—C2A—H2AA109.6C15B—C14B—C13B119.8 (2)
C3A—C2A—H2AB109.6C15B—C14B—H14B120.1
C1A—C2A—H2AB109.6C13B—C14B—H14B120.1
H2AA—C2A—H2AB108.2C14A—C15A—C10A120.7 (2)
N2A—C3A—C2A111.2 (2)C14A—C15A—H15A119.6
N2A—C3A—H3AA109.4C10A—C15A—H15A119.6
C2A—C3A—H3AA109.4C14B—C15B—C10B121.2 (2)
N2A—C3A—H3AB109.4C14B—C15B—H15B119.4
C2A—C3A—H3AB109.4C10B—C15B—H15B119.4
H3AA—C3A—H3AB108.0C17B—C16B—O4B110.6 (2)
N1A—C4A—N2A118.30 (19)C17B—C16B—C5B133.6 (2)
N1A—C4A—C8A120.18 (18)O4B—C16B—C5B115.78 (18)
N2A—C4A—C8A121.52 (18)C17A—C16A—O4A110.4 (2)
N1B—C4B—N2B118.0 (2)C17A—C16A—C5A134.0 (2)
N1B—C4B—C8B120.21 (19)O4A—C16A—C5A115.6 (2)
N2B—C4B—C8B121.77 (19)C16B—C17B—C18B106.3 (2)
N2A—C5A—C16A110.09 (18)C16B—C17B—H17A126.9
N2A—C5A—C6A111.40 (17)C18B—C17B—H17A126.9
C16A—C5A—C6A112.28 (19)C19B—C18B—C17B106.9 (2)
N2A—C5A—H5AA107.6C19B—C18B—H18A126.5
C16A—C5A—H5AA107.6C17B—C18B—H18A126.5
C6A—C5A—H5AA107.6C18B—C19B—O4B110.4 (2)
N2B—C5B—C16B110.12 (19)C18B—C19B—H19A124.8
N2B—C5B—C6B111.65 (18)O4B—C19B—H19A124.8
C16B—C5B—C6B109.94 (19)C16A—C17A—C18A105.2 (3)
N2B—C5B—H5BA108.3C16A—C17A—H17B127.4
C16B—C5B—H5BA108.3C18A—C17A—H17B127.4
C6B—C5B—H5BA108.3C19A—C18A—C17A107.1 (3)
C7A—C6A—C5A111.15 (17)C19A—C18A—H18B126.5
C7A—C6A—N3A110.20 (18)C17A—C18A—H18B126.5
C5A—C6A—N3A110.05 (18)C18A—C19A—O4A110.6 (3)
C7A—C6A—H6AA108.5C18A—C19A—H19B124.7
C5A—C6A—H6AA108.5O4A—C19A—H19B124.7
N3A—C6A—H6AA108.5C19A—O4A—C16A106.7 (3)
C4A—N1A—C1A—C2A18.9 (3)C6A—C7A—C8A—C9A154.7 (2)
C4B—N1B—C1B—C2B3.5 (10)C6A—C7A—C8A—C4A26.1 (3)
C4B—N1B—C1B—C2D31.7 (4)N1B—C4B—C8B—C9B2.6 (3)
C4B—N2B—C3B—C2D14.8 (5)N2B—C4B—C8B—C9B175.7 (2)
C5B—N2B—C3B—C2D167.2 (4)N1B—C4B—C8B—C7B179.52 (19)
C4B—N2B—C3B—C2B21.1 (9)N2B—C4B—C8B—C7B2.2 (3)
C5B—N2B—C3B—C2B157.0 (8)C6B—C7B—C8B—C9B146.8 (2)
N1B—C1B—C2B—C3B22.3 (18)C6B—C7B—C8B—C4B31.0 (3)
C2D—C1B—C2B—C3B64.8 (12)C4A—C8A—C9A—O1A1.8 (3)
C2D—C3B—C2B—C1B68.9 (11)C7A—C8A—C9A—O1A178.90 (19)
N2B—C3B—C2B—C1B30.2 (17)C4A—C8A—C9A—C10A179.19 (18)
C2B—C3B—C2D—C1B55.2 (7)C7A—C8A—C9A—C10A0.1 (3)
N2B—C3B—C2D—C1B40.6 (6)C4B—C8B—C9B—O1B4.1 (3)
C2B—C1B—C2D—C3B59.6 (7)C7B—C8B—C9B—O1B178.2 (2)
N1B—C1B—C2D—C3B47.5 (6)C4B—C8B—C9B—C10B172.25 (19)
N1A—C1A—C2A—C3A49.2 (3)C7B—C8B—C9B—C10B5.5 (3)
C4A—N2A—C3A—C2A28.4 (3)O1A—C9A—C10A—C11A128.2 (2)
C5A—N2A—C3A—C2A145.9 (2)C8A—C9A—C10A—C11A52.7 (3)
C1A—C2A—C3A—N2A54.2 (3)O1A—C9A—C10A—C15A47.8 (3)
C1A—N1A—C4A—N2A8.3 (3)C8A—C9A—C10A—C15A131.3 (2)
C1A—N1A—C4A—C8A172.0 (2)O1B—C9B—C10B—C11B131.8 (2)
C5A—N2A—C4A—N1A177.48 (19)C8B—C9B—C10B—C11B51.6 (3)
C3A—N2A—C4A—N1A3.6 (3)O1B—C9B—C10B—C15B45.1 (3)
C5A—N2A—C4A—C8A2.9 (3)C8B—C9B—C10B—C15B131.5 (2)
C3A—N2A—C4A—C8A176.8 (2)C15A—C10A—C11A—C12A2.4 (3)
C1B—N1B—C4B—N2B5.9 (3)C9A—C10A—C11A—C12A178.36 (18)
C1B—N1B—C4B—C8B172.5 (2)C15B—C10B—C11B—C12B0.3 (3)
C3B—N2B—C4B—N1B3.8 (3)C9B—C10B—C11B—C12B177.24 (19)
C5B—N2B—C4B—N1B174.1 (2)C10B—C11B—C12B—C13B0.5 (3)
C3B—N2B—C4B—C8B177.9 (2)C10A—C11A—C12A—C13A0.1 (3)
C5B—N2B—C4B—C8B4.2 (3)C11A—C12A—C13A—C14A1.8 (3)
C4A—N2A—C5A—C16A97.1 (2)C11B—C12B—C13B—C14B0.6 (3)
C3A—N2A—C5A—C16A77.1 (2)C12A—C13A—C14A—C15A1.3 (4)
C4A—N2A—C5A—C6A28.1 (3)C12B—C13B—C14B—C15B0.2 (3)
C3A—N2A—C5A—C6A157.7 (2)C13A—C14A—C15A—C10A1.1 (3)
C4B—N2B—C5B—C16B103.4 (2)C11A—C10A—C15A—C14A2.9 (3)
C3B—N2B—C5B—C16B78.5 (2)C9A—C10A—C15A—C14A179.09 (19)
C4B—N2B—C5B—C6B19.0 (3)C13B—C14B—C15B—C10B1.0 (3)
C3B—N2B—C5B—C6B159.1 (2)C11B—C10B—C15B—C14B1.1 (3)
N2A—C5A—C6A—C7A51.2 (2)C9B—C10B—C15B—C14B178.21 (19)
C16A—C5A—C6A—C7A72.8 (2)C19B—O4B—C16B—C17B0.1 (3)
N2A—C5A—C6A—N3A71.2 (2)C19B—O4B—C16B—C5B178.80 (19)
C16A—C5A—C6A—N3A164.79 (18)N2B—C5B—C16B—C17B34.3 (4)
O3A—N3A—C6A—C7A139.3 (2)C6B—C5B—C16B—C17B89.1 (3)
O2A—N3A—C6A—C7A44.7 (3)N2B—C5B—C16B—O4B147.02 (18)
O3A—N3A—C6A—C5A16.4 (3)C6B—C5B—C16B—O4B89.5 (2)
O2A—N3A—C6A—C5A167.7 (2)N2A—C5A—C16A—C17A32.9 (4)
O3B—N3B—C6B—C5B176.92 (19)C6A—C5A—C16A—C17A91.8 (3)
O2B—N3B—C6B—C5B3.7 (3)N2A—C5A—C16A—O4A144.83 (19)
O3B—N3B—C6B—C7B53.3 (3)C6A—C5A—C16A—O4A90.4 (2)
O2B—N3B—C6B—C7B127.3 (2)O4B—C16B—C17B—C18B0.1 (3)
N2B—C5B—C6B—N3B74.8 (2)C5B—C16B—C17B—C18B178.6 (2)
C16B—C5B—C6B—N3B162.72 (16)C16B—C17B—C18B—C19B0.0 (3)
N2B—C5B—C6B—C7B47.3 (2)C17B—C18B—C19B—O4B0.1 (3)
C16B—C5B—C6B—C7B75.3 (2)C16B—O4B—C19B—C18B0.2 (3)
N3B—C6B—C7B—C8B69.9 (2)O4A—C16A—C17A—C18A0.0 (3)
C5B—C6B—C7B—C8B53.4 (2)C5A—C16A—C17A—C18A177.8 (3)
C5A—C6A—C7A—C8A50.4 (2)C16A—C17A—C18A—C19A0.2 (3)
N3A—C6A—C7A—C8A71.9 (2)C17A—C18A—C19A—O4A0.3 (4)
N1A—C4A—C8A—C9A0.5 (3)C18A—C19A—O4A—C16A0.3 (3)
N2A—C4A—C8A—C9A179.12 (19)C17A—C16A—O4A—C19A0.2 (3)
N1A—C4A—C8A—C7A178.80 (19)C5A—C16A—O4A—C19A178.5 (2)
N2A—C4A—C8A—C7A1.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O1A0.881.842.553 (2)137
N1B—H1BA···O1B0.881.852.556 (3)136
C6A—H6AA···O1B1.002.363.103 (3)130
C7A—H7AB···O2A0.992.442.790 (3)100

Experimental details

Crystal data
Chemical formulaC19H19N3O4
Mr353.37
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)13.506 (3), 17.675 (4), 14.755 (3)
β (°) 105.12 (3)
V3)3400.3 (12)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.44 × 0.43 × 0.37
Data collection
DiffractometerRigaku R-AXIS RAPID IP area-detector
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.958, 0.964
No. of measured, independent and
observed [I > 2σ(I)] reflections
11765, 5990, 4405
Rint0.024
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.126, 1.02
No. of reflections5990
No. of parameters479
No. of restraints40
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.59, 0.26

Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELX97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1AA···O1A0.881.842.553 (2)136.7
N1B—H1BA···O1B0.881.852.556 (3)135.7
C6A—H6AA···O1B1.002.363.103 (3)130
C7A—H7AB···O2A0.992.442.790 (3)100
 

Acknowledgements

We thank Tongling Liang and Xiang Hao at the Chinese Academy of Sciences for the X-ray crystallographic determination.

References

First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
First citationHuang, Z.-T. & Wang, M.-X. (1994). Heterocycles, 37, 1233–1262.  CrossRef CAS
First citationRigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationYaqub, M., Yu, C.-Y., Jia, Y.-M. & Huang, Z.-T. (2008). Synlett, 9, 1357–1360.
First citationYu, C.-Y., Yang, P.-H., Zhao, M.-X. & Huang, Z.-T. (2006). Synlett, pp. 1835–1840.  Web of Science CrossRef
First citationYu, C.-Y., Yuan, X.-N. & Huang, Z.-T. (2007). Acta Cryst. E63, o3186.  Web of Science CSD CrossRef IUCr Journals

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.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds