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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 3| March 2015| Pages o177-o178
doi:10.1107/S2056989015002698

Crystal structure of (4Z)-4-{[(2-chloro­phen­yl)amino](furan-2-yl)methyl­­idene}-3-methyl-1-phenyl-4,5-di­hydro-1H-pyrazol-5-one

CROSSMARK_Color_square_no_text.svg
Heng-Qiang Zhang,a* Xing Yang,a Qiong Wua and Hong-Li Chena

aDepartment of Chemistry, Hebei Normal University for Nationalities, Chengde, 067000, People's Republic of China
*Correspondence e-mail: zhanghengqiang80@163.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 7 February 2015; accepted 8 February 2015; online 13 February 2015)

In the title compound, C21H16ClN3O2, the pyrazolone ring and the O=C—C=C—N mean plane [maximum deviation = 0.022 (2) Å] are nearly coplanar, making a dihedral angle 4.56 (8)°, while the phenyl and pyrazole rings subtend a dihedral angle of 19.75 (8)°. The compound is in the enamine–keto form and its structure is stabilized by an intra­molecular N—H⋯O hydrogen bond. In the crystal, mol­ecules are linked via C—H⋯N hydrogen bonds, forming chains along [010]. Between the chains there are π–π inter­actions [inter-centroid distances = 3.3902 (9) and 3.5956 (11) Å], linking the chains to form sheets parallel to (10-1).

CCDC reference: 1048268

1. Related literature

For details of the synthesis of 4-heterocyclic acylpyrazolones, see: Jensen (1959[Jensen, B. S. (1959). Acta Chem. Scand. 13, 1668-1670.]); Dong et al. (1983[Dong, X.-C., Liu, F.-C. & Zhao, Y.-L. (1983). Acta Chim. Sinica, 41, 848-852.]). For applications of 4-pyrazolo­nes, see: Casas et al. (2007[Casas, J. S., García-Tasende, M. S., Sanchez, A., Sordo, J. & Touceda, Á. (2007). Coord. Chem. Rev. 251,1561-1589.]). For the anti­bacterial activity of pyrazolone derivatives, see: Li et al. (2000[Li, J. Z., Li, G. & Yu, W. J. (2000). J. Rare Earths 18, 233-236.]); Zhang et al. (2008[Zhang, H. Q., Li, J. Z., Zhang, Y. & Zhang, D. (2008). Chin. J. Inorg. Chem. 24, 990-993.]); Raman et al. (2001[Raman, N., Kulandaisamy, A., Shunmugasundaram, A. & Jeyasubramanian, K. (2001). Transition Met. Chem. 26, 131-135.]). For related structures, see: Zhang et al. (2007[Zhang, H.-Q., Li, J.-Z., Zhang, Y., Zhang, D. & Su, Z.-H. (2007). Acta Cryst. E63, o3536.]); Li et al. (2009[Li, J., Li, J.-Z., Li, J.-Q., Zhang, H.-Q. & Li, J.-M. (2009). Acta Cryst. E65, o1824.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C21H16ClN3O2

  • Mr = 377.82

  • Monoclinic, C 2/c

  • a = 17.1008 (16) Å

  • b = 12.4737 (12) Å

  • c = 17.9070 (17) Å

  • β = 111.276 (2)°

  • V = 3559.4 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 295 K

  • 0.28 × 0.25 × 0.21 mm

2.2. Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • 11255 measured reflections

  • 4048 independent reflections

  • 3245 reflections with I > 2σ(I)

  • Rint = 0.025

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.095

  • S = 1.01

  • 4048 reflections

  • 245 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H3A⋯O1 0.86 2.00 2.678 (2) 135
C15—H15⋯N2i 0.93 2.59 3.282 (2) 131
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.] and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON.

Supporting information

CCDC reference: 1048268

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015002698/su5081sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015002698/su5081Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015002698/su5081Isup3.cml

checkCIF report


Comment top

Pyrazolone derivatives, especially 4-acylpyrazolone, form an important class of organic compounds and represent a significant scientific and applied interest in biological, analytic applications, catalysis, dye and extraction metallurgy (Raman et al., 2001; Casas, et al., 2007). 1-phenyl-3-methyl-4-(2-furoyl)-5-pyrazolone (HPMFP), is a member of a family of 4-heterocyclic acylpyrazolones, first synthesized in 1983 (Dong et al., 1983). In recent years, we have reported on Schiff bases derived from HPMFP and their complexes, which possess high antibacterial activity (Li et al., 2000; Zhang et al., 2008). In order to further investigate the coordination abilities and the behaviour of pyrazolone based ligands, we extended the study to the syntheses of new title pyrazolone derivative, and report herein on its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. The phenyl ring (C1-C6) is twisted by 19.75 (4)° with respect to a plane defined by the pyrazole ring (N1/N2/C7-C9). The pyrazole ring and the (O1/C7/C8/C11/N3) mean plane [maximum deviation = 0.022 (2) Å for atom C7] are nearly coplanar with a dihedral angle 4.56 (8) °. The bond length C8═C11 (1.384 (2) Å) lies between the usual C—C and C═C bond lengths and indicates the delocalization of the electrons because of the addition of a proton to atom N3 which is more favorable than to O1, as shown in the difference Fourier map. Atoms O1 and N3 are on the same side of the C8═C11 bond, hence available for complexation with metals. A strong intramolecular hydrogen bond N3—H3A···O1 (Fig. 1 and Table 1) is also indicative of the enamine-keto form. All bond lengths and angles are normal and comparable with those found for related compounds (Zhang et al., 2007; Li et al., 2009).

In the crystal, molecules are linked via C-H···N hydrogen bonds forming chains along [010]; see Table 1 and Fig. 2. Between the chains there are π-π interactions linking the chains to form sheets parallel to (101) [inter-centroid distances are Cg2···Cg2i = 3.3902 (9) Å and Cg4···Cg4i = 3.5956 (11) Å; Cg2 and Cg4 are the centroids of rings N1/N2/C7-C9 and C16-C21, respectively; symmetry code: (i) -x+1, -y, -z+1].

Related literature top

For details of the synthesis, see: Jensen (1959); Dong et al. (1983). For applications of 4-pyrazolones, see: Casas et al. (2007). For the antibacterial activity of pyrazolone derivatives, see: Li et al. (2000); Zhang et al. (2008); Raman et al. (2001). For related structures, see: Zhang et al. (2007); Li et al. (2009).

Experimental top

The starting compound HPMFP was synthesized according to the method proposed by Jensen (1959). A mixture of a 10 ml HPMFP (2 mmol, 0.5366 g) anhydrous ethanol solution, and a 0.21 ml of an o-chloroaniline (2 mmol, 0.2545 g) solution was refluxed for ca. 5 h, adding a few drops of glacial acetic acid as a catalyst. Then ethanol was removed by evaporation and the resulting black precipitate formed was filtered off, washed with cold anhydrous ethanol and dried in air. Yellow block-like crystals were obtained by slow evaporation of a solution in anhydrous ethanol at room temperature after a few days.

Refinement top

The H atom bonded to N3 was located in a difference Fourier map and freely refined. The C-bound H atoms were placed in calculated positions and refined as riding: C—H = 0.93 - 0.97 Å with Uiso(H) = 1.5eqU(C) for methyl H atoms and = 1.2eq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 and PLATON (Spek, 2009); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at 30% probability level.
[Figure 2] Fig. 2. A perspective view along the b axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity).
(4Z)-4-{[(2-Chlorophenyl)amino](furan-2-yl)methylidene}-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one top
Crystal data top
C21H16ClN3O2F(000) = 1568
Mr = 377.82Dx = 1.410 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3518 reflections
a = 17.1008 (16) Åθ = 2.6–27.3°
b = 12.4737 (12) ŵ = 0.24 mm−1
c = 17.9070 (17) ÅT = 295 K
β = 111.276 (2)°Block, yellow
V = 3559.4 (6) Å30.28 × 0.25 × 0.21 mm
Z = 8
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3245 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 27.4°, θmin = 2.1°
phi and ω scansh = −22→22
11255 measured reflectionsk = −16→16
4048 independent reflectionsl = −11→23
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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0422P)2 + 2.6702P]
where P = (Fo2 + 2Fc2)/3
4048 reflections(Δ/σ)max = 0.001
245 parametersΔρmax = 0.30 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Crystal data top
C21H16ClN3O2V = 3559.4 (6) Å3
Mr = 377.82Z = 8
Monoclinic, C2/cMo Kα radiation
a = 17.1008 (16) ŵ = 0.24 mm−1
b = 12.4737 (12) ÅT = 295 K
c = 17.9070 (17) Å0.28 × 0.25 × 0.21 mm
β = 111.276 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3245 reflections with I > 2σ(I)
11255 measured reflectionsRint = 0.025
4048 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.095H-atom parameters constrained
S = 1.01Δρmax = 0.30 e Å−3
4048 reflectionsΔρmin = −0.33 e Å−3
245 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
C10.44525 (8)0.57307 (12)0.57260 (8)0.0224 (3)
C20.40060 (9)0.51564 (12)0.50340 (8)0.0243 (3)
H20.40790.44200.50140.029*
C30.34516 (9)0.56928 (13)0.43753 (9)0.0293 (3)
H30.31520.53110.39140.035*
C40.33398 (10)0.67869 (14)0.43979 (10)0.0350 (4)
H40.29700.71420.39530.042*
C50.37828 (10)0.73525 (13)0.50892 (10)0.0356 (4)
H50.37070.80890.51070.043*
C60.43372 (9)0.68315 (12)0.57541 (10)0.0288 (3)
H60.46310.72160.62160.035*
C70.51617 (9)0.41344 (12)0.65574 (8)0.0226 (3)
C80.59225 (8)0.40755 (12)0.72738 (8)0.0226 (3)
C90.61904 (9)0.51729 (12)0.74541 (8)0.0231 (3)
C100.69450 (9)0.56344 (13)0.80961 (9)0.0288 (3)
H10A0.70040.63750.79800.043*
H10B0.74370.52460.81160.043*
H10C0.68780.55780.86040.043*
C110.62715 (9)0.31029 (12)0.75986 (8)0.0234 (3)
C120.70547 (9)0.30187 (12)0.82951 (9)0.0243 (3)
C130.73360 (9)0.34085 (13)0.90500 (9)0.0291 (3)
H130.70520.38700.92710.035*
C140.81512 (10)0.29751 (14)0.94399 (9)0.0312 (3)
H140.85050.30980.99660.037*
C150.83107 (9)0.23514 (13)0.88992 (9)0.0287 (3)
H150.88050.19700.89970.034*
C160.60305 (9)0.11363 (12)0.75154 (9)0.0268 (3)
C170.62669 (10)0.09001 (14)0.83295 (10)0.0337 (4)
H170.63580.14540.86990.040*
C180.63667 (10)−0.01516 (15)0.85909 (11)0.0409 (4)
H180.6530−0.03000.91350.049*
C190.62263 (10)−0.09799 (15)0.80517 (13)0.0435 (5)
H190.6304−0.16850.82330.052*
C200.59700 (10)−0.07661 (14)0.72421 (12)0.0390 (4)
H200.5864−0.13260.68760.047*
C210.58720 (9)0.02863 (13)0.69779 (10)0.0302 (3)
Cl10.55346 (3)0.05471 (4)0.59572 (3)0.04238 (13)
N10.50433 (7)0.52104 (10)0.63947 (7)0.0226 (3)
N20.56763 (7)0.58347 (10)0.69457 (7)0.0244 (3)
N30.59039 (8)0.21931 (10)0.72231 (7)0.0271 (3)
H3A0.55460.22710.67440.033*
O10.47138 (6)0.33913 (8)0.61635 (6)0.0261 (2)
O20.76468 (6)0.23556 (8)0.81867 (6)0.0259 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0186 (6)0.0280 (7)0.0231 (7)0.0013 (5)0.0104 (6)0.0028 (6)
C20.0228 (7)0.0272 (7)0.0240 (7)0.0006 (6)0.0099 (6)0.0010 (6)
C30.0247 (7)0.0381 (9)0.0241 (7)0.0017 (6)0.0079 (6)0.0027 (6)
C40.0301 (8)0.0403 (9)0.0315 (8)0.0086 (7)0.0074 (7)0.0095 (7)
C50.0354 (8)0.0282 (8)0.0421 (10)0.0082 (7)0.0127 (7)0.0045 (7)
C60.0271 (7)0.0281 (8)0.0304 (8)0.0012 (6)0.0094 (6)−0.0023 (6)
C70.0227 (7)0.0265 (7)0.0201 (7)0.0000 (6)0.0097 (6)0.0009 (6)
C80.0215 (7)0.0286 (7)0.0179 (7)−0.0010 (6)0.0074 (5)−0.0005 (5)
C90.0213 (6)0.0289 (7)0.0211 (7)−0.0009 (6)0.0102 (6)−0.0023 (6)
C100.0258 (7)0.0336 (8)0.0243 (7)−0.0040 (6)0.0058 (6)−0.0039 (6)
C110.0243 (7)0.0295 (7)0.0178 (7)−0.0003 (6)0.0092 (6)−0.0005 (6)
C120.0237 (7)0.0277 (7)0.0226 (7)0.0024 (6)0.0099 (6)0.0016 (6)
C130.0288 (7)0.0367 (9)0.0224 (7)0.0039 (6)0.0101 (6)−0.0009 (6)
C140.0265 (7)0.0437 (9)0.0208 (7)0.0012 (7)0.0054 (6)0.0031 (6)
C150.0210 (7)0.0352 (8)0.0278 (8)0.0036 (6)0.0062 (6)0.0067 (6)
C160.0207 (7)0.0283 (8)0.0306 (8)0.0015 (6)0.0084 (6)0.0035 (6)
C170.0293 (8)0.0387 (9)0.0292 (8)−0.0028 (7)0.0059 (7)0.0058 (7)
C180.0289 (8)0.0452 (10)0.0430 (10)−0.0031 (7)0.0064 (7)0.0176 (8)
C190.0271 (8)0.0351 (9)0.0668 (13)0.0025 (7)0.0151 (8)0.0189 (9)
C200.0288 (8)0.0295 (9)0.0619 (12)−0.0015 (7)0.0203 (8)−0.0023 (8)
C210.0240 (7)0.0322 (8)0.0355 (8)−0.0012 (6)0.0122 (6)−0.0005 (7)
Cl10.0543 (3)0.0414 (2)0.0326 (2)−0.0103 (2)0.01723 (19)−0.01043 (18)
N10.0204 (6)0.0253 (6)0.0206 (6)−0.0018 (5)0.0057 (5)−0.0014 (5)
N20.0216 (6)0.0279 (6)0.0229 (6)−0.0032 (5)0.0071 (5)−0.0039 (5)
N30.0291 (6)0.0281 (7)0.0196 (6)0.0012 (5)0.0034 (5)0.0014 (5)
O10.0252 (5)0.0264 (5)0.0232 (5)−0.0031 (4)0.0045 (4)−0.0001 (4)
O20.0243 (5)0.0291 (5)0.0250 (5)0.0030 (4)0.0097 (4)0.0003 (4)
Geometric parameters (Å, º) top
C1—C61.391 (2)C11—C121.466 (2)
C1—C21.395 (2)C12—C131.350 (2)
C1—N11.4135 (18)C12—O21.3746 (17)
C2—C31.388 (2)C13—C141.420 (2)
C2—H20.9300C13—H130.9300
C3—C41.381 (2)C14—C151.345 (2)
C3—H30.9300C14—H140.9300
C4—C51.387 (2)C15—O21.3659 (18)
C4—H40.9300C15—H150.9300
C5—C61.385 (2)C16—C211.391 (2)
C5—H50.9300C16—C171.396 (2)
C6—H60.9300C16—N31.4058 (19)
C7—O11.2456 (17)C17—C181.382 (2)
C7—N11.3727 (19)C17—H170.9300
C7—C81.4602 (19)C18—C191.375 (3)
C8—C111.384 (2)C18—H180.9300
C8—C91.442 (2)C19—C201.380 (3)
C9—N21.3047 (19)C19—H190.9300
C9—C101.497 (2)C20—C211.385 (2)
C10—H10A0.9600C20—H200.9300
C10—H10B0.9600C21—Cl11.7362 (17)
C10—H10C0.9600N1—N21.4060 (16)
C11—N31.3522 (19)N3—H3A0.8600
C6—C1—C2120.02 (13)C13—C12—C11135.20 (14)
C6—C1—N1119.33 (13)O2—C12—C11114.55 (12)
C2—C1—N1120.62 (13)C12—C13—C14106.54 (14)
C3—C2—C1119.50 (14)C12—C13—H13126.7
C3—C2—H2120.3C14—C13—H13126.7
C1—C2—H2120.3C15—C14—C13106.59 (14)
C4—C3—C2120.72 (15)C15—C14—H14126.7
C4—C3—H3119.6C13—C14—H14126.7
C2—C3—H3119.6C14—C15—O2110.69 (13)
C3—C4—C5119.49 (15)C14—C15—H15124.7
C3—C4—H4120.3O2—C15—H15124.7
C5—C4—H4120.3C21—C16—C17118.14 (15)
C6—C5—C4120.68 (15)C21—C16—N3119.48 (14)
C6—C5—H5119.7C17—C16—N3122.27 (14)
C4—C5—H5119.7C18—C17—C16120.49 (17)
C5—C6—C1119.59 (15)C18—C17—H17119.8
C5—C6—H6120.2C16—C17—H17119.8
C1—C6—H6120.2C19—C18—C17120.45 (17)
O1—C7—N1126.47 (13)C19—C18—H18119.8
O1—C7—C8128.96 (13)C17—C18—H18119.8
N1—C7—C8104.56 (12)C18—C19—C20120.05 (16)
C11—C8—C9133.20 (13)C18—C19—H19120.0
C11—C8—C7121.62 (13)C20—C19—H19120.0
C9—C8—C7104.97 (12)C19—C20—C21119.67 (17)
N2—C9—C8111.44 (13)C19—C20—H20120.2
N2—C9—C10117.86 (13)C21—C20—H20120.2
C8—C9—C10130.69 (13)C20—C21—C16121.15 (16)
C9—C10—H10A109.5C20—C21—Cl1119.34 (14)
C9—C10—H10B109.5C16—C21—Cl1119.51 (12)
H10A—C10—H10B109.5C7—N1—N2112.08 (11)
C9—C10—H10C109.5C7—N1—C1129.33 (12)
H10A—C10—H10C109.5N2—N1—C1118.15 (12)
H10B—C10—H10C109.5C9—N2—N1106.94 (12)
N3—C11—C8118.36 (13)C11—N3—C16128.37 (13)
N3—C11—C12118.65 (13)C11—N3—H3A115.8
C8—C11—C12122.83 (13)C16—N3—H3A115.8
C13—C12—O2110.18 (13)C15—O2—C12106.00 (11)
C6—C1—C2—C30.3 (2)N3—C16—C17—C18178.52 (14)
N1—C1—C2—C3−177.69 (12)C16—C17—C18—C19−0.6 (2)
C1—C2—C3—C40.2 (2)C17—C18—C19—C20−1.1 (3)
C2—C3—C4—C5−0.5 (2)C18—C19—C20—C211.3 (2)
C3—C4—C5—C60.2 (2)C19—C20—C21—C160.2 (2)
C4—C5—C6—C10.3 (2)C19—C20—C21—Cl1−179.07 (12)
C2—C1—C6—C5−0.6 (2)C17—C16—C21—C20−1.9 (2)
N1—C1—C6—C5177.51 (13)N3—C16—C21—C20−178.43 (14)
O1—C7—C8—C112.7 (2)C17—C16—C21—Cl1177.36 (11)
N1—C7—C8—C11−176.44 (12)N3—C16—C21—Cl10.88 (19)
O1—C7—C8—C9178.06 (14)O1—C7—N1—N2−178.37 (12)
N1—C7—C8—C9−1.11 (14)C8—C7—N1—N20.82 (15)
C11—C8—C9—N2175.64 (15)O1—C7—N1—C1−6.2 (2)
C7—C8—C9—N21.09 (16)C8—C7—N1—C1173.00 (12)
C11—C8—C9—C10−2.8 (3)C6—C1—N1—C7167.80 (14)
C7—C8—C9—C10−177.36 (14)C2—C1—N1—C7−14.1 (2)
C9—C8—C11—N3−171.97 (14)C6—C1—N1—N2−20.42 (18)
C7—C8—C11—N31.8 (2)C2—C1—N1—N2157.62 (12)
C9—C8—C11—C123.4 (2)C8—C9—N2—N1−0.60 (15)
C7—C8—C11—C12177.17 (12)C10—C9—N2—N1178.07 (11)
N3—C11—C12—C13−129.37 (19)C7—N1—N2—C9−0.17 (15)
C8—C11—C12—C1355.3 (2)C1—N1—N2—C9−173.31 (11)
N3—C11—C12—O247.33 (18)C8—C11—N3—C16−165.70 (14)
C8—C11—C12—O2−127.98 (14)C12—C11—N3—C1618.8 (2)
O2—C12—C13—C140.34 (18)C21—C16—N3—C11−154.71 (15)
C11—C12—C13—C14177.15 (16)C17—C16—N3—C1129.0 (2)
C12—C13—C14—C15−0.11 (19)C14—C15—O2—C120.37 (17)
C13—C14—C15—O2−0.17 (18)C13—C12—O2—C15−0.44 (16)
C21—C16—C17—C182.1 (2)C11—C12—O2—C15−177.97 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O10.862.002.678 (2)135
C15—H15···N2i0.932.593.282 (2)131
Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O10.862.002.678 (2)135
C15—H15···N2i0.932.593.282 (2)131
Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.
 

Acknowledgements

We thank the Science Foundation of Hebei Normal University for Nationalities (project No. 20120005), the Department of Science and Technology of Hebei province (project No.12211502), the Chengde Municipal Finance Bureau Foundation (projects Nos. CZ2012004 and CZ2014001) and the program for Outstanding Young-aged Innovative Talents of Higher Learning Institutions of Hebei Province (project No. BJ201404) for financial support.

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ISSN: 2056-9890
Volume 71| Part 3| March 2015| Pages o177-o178
doi:10.1107/S2056989015002698
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