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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

(Z)-Ethyl 3-[bis­­(4-chloro-3-ethyl-1-methyl-1H-pyrazol-5-yl­carbon­yl)amino]-3-(4-chloro­phen­yl)-2-cyano­propanoate

aDepartment of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, People's Republic of China, bSchool of Mathematics and Physics, Huangshi Institute of Technology, Huangshi 435003, People's Republic of China, and cDepartment of Chemistry, Changsha Medical University, Changsha 410219, People's Republic of China
*Correspondence e-mail: zhangdehua200@163.com

(Received 3 December 2008; accepted 11 March 2009; online 28 March 2009)

The title compound, C26H25Cl3N6O4, was prepared by the reaction of (Z)-ethyl 3-amino-3-(4-chloro­phen­yl)-2-cyano­acrylate and 4-chloro-3-ethyl-1-methyl-1H-pyrazole-5-carbonyl chloride. The dihedral angles between the chloro­benzene and the two pyrazole rings are 59.8 (2) and 33.3 (2)°. The two pyrazole rings are oriented to each other at a dihedral angle of 84.7 (2)°. The crystal packing is governed by inter­molecular C—H⋯O inter­actions, resulting in a three-dimensional network. The ethyl groups are disordered over two positions, with site-occupancy factors of 0.71/0.29 and 0.51/0.49.

Related literature

Several novel acrylate compounds are useful as inhibitors of Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea and Gibberella zeae; see: Heller et al. (2004[Heller, D., Drexler, H. J., You, J. & Zhang, S. L. (2004). WO Patent 011414.]); Creagh & Hubbell (1992[Creagh, D. C & Hubbell, J. H. (1992). International Tables for Crystallography, Vol. C, pp. 200-206. Dordrecht: Kluwer.]); Ibers & Hamilton (1964[Ibers, J. A. & Hamilton, W. C. (1964). Acta Cryst. 17, 781-782.]).

[Scheme 1]

Experimental

Crystal data
  • C26H25Cl3N6O4

  • Mr = 591.87

  • Monoclinic, P 21 /c

  • a = 10.7277 (3) Å

  • b = 16.1476 (5) Å

  • c = 17.3109 (5) Å

  • β = 107.671 (2)°

  • V = 2857.21 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.36 mm−1

  • T = 298 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: none

  • 18010 measured reflections

  • 5600 independent reflections

  • 3595 reflections with I > 2σ(I)

  • Rint = 0.045

Refinement
  • R[F2 > 2σ(F2)] = 0.065

  • wR(F2) = 0.170

  • S = 1.02

  • 5600 reflections

  • 397 parameters

  • 12 restraints

  • H-atom parameters constrained

  • Δρmax = 0.33 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C13—H13⋯O2i 0.93 2.59 3.420 (5) 149
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART. Bruker AXS Inc., Madison,Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SMART. 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

Recently, 2-cyanoacrylates have been in widespread used as agrochemicals because of their unique mechanism of action and good environmental profiles. The title compound is useful as an inhibitor of Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea and Gibberella zeae (Heller et al., 2004; Ibers & Hamilton, 1964). In the title compound (Fig. 1), all bond lengths and angles are unexceptional. The planar chlorobenzene ring is approximately perpendicular to one of the pyrazole ring with a dihedral angle of 59.9 (2)°. The dihedral angle between this chlorobenzene ring and the other pyrazole rings is 33.3 (12)°. The dihedral angle between the two pyrazole rings is 84.7 (2)°. The crystal packing is governed by C—H···O intermolecular interactions resulting in a three-dimensional network (Table 1.). The ethyl groups are disordered over two positions, with site-occupancy factors of 0.71/0.29 and 0.51/0.49.

Related literature top

Several novel acrylate compounds are useful as inhibitors of Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea and Gibberella zeae, see: Heller et al. (2004); Creagh & Hubbell (1992); Ibers & Hamilton (1964).

Experimental top

To a solution of (Z)-ethyl 3-amino-3-(4-chlorophenyl)-2-cyanoacrylate (1.25 g, 0.0050 mol) in C1H2Cl2(18 ml), 4-chloro-3-ethyl-1-methyl- 1H-pyrazole-5-carbonyl chloride (3.11 g, 0.015 mol) was added. Subsequently, Et3N1(1.52 g, 0.015 mol) was dropped into the solution under stirring. The reaction mixture was then heated to reflux, stirred for 4 h. Subsequently, it was cooled to room temperature. The reaction solution was filtered off and some white solid was separated. The organic phase was washed with water and then dried over Na2S1O4. After removal of the solvent, a brown dope was obtained. After column chromatogram using ethylacetate/light petroleum (1:6) as the eluent, small single crystals were grown from a solution of ethyl acetate/petroleum ether(3:1) after 45 days, at room temperature.

Refinement top

Methyl H atoms were placed in calculated positions with C—H=0.96Å and the torsion angle was refined to fit the electron density; thermal parameters were refined as Uiso(H)=1.5Ueq(C). Other H atoms were placed in calculated positions with C—H =0.96Å (methylene C—H) and 0.93Å (aromatic C—H), and refined in riding mode, with Uiso(H)=1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1999); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Only the higher occupied of the disordered sites is shown.
[Figure 2] Fig. 2. The packing of the title compound, viewed down the c-axis.
(Z)-Ethyl 3-[bis(4-chloro-3-ethyl-1-methyl-1H-pyrazol-5- ylcarbonyl)amino]-3-(4-chlorophenyl)-2-cyanopropanoate top
Crystal data top
C26H25Cl3N6O4F(000) = 1224
Mr = 591.87Dx = 1.376 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2499 reflections
a = 10.7277 (3) Åθ = 2.4–20.2°
b = 16.1476 (5) ŵ = 0.36 mm1
c = 17.3109 (5) ÅT = 298 K
β = 107.671 (2)°Block, colorless
V = 2857.21 (14) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3595 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.045
Graphite monochromatorθmax = 26.0°, θmin = 1.8°
ϕ and ω scansh = 1313
18010 measured reflectionsk = 1419
5600 independent reflectionsl = 1921
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0809P)2 + 0.6207P]
where P = (Fo2 + 2Fc2)/3
5600 reflections(Δ/σ)max < 0.001
397 parametersΔρmax = 0.33 e Å3
12 restraintsΔρmin = 0.21 e Å3
Crystal data top
C26H25Cl3N6O4V = 2857.21 (14) Å3
Mr = 591.87Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.7277 (3) ŵ = 0.36 mm1
b = 16.1476 (5) ÅT = 298 K
c = 17.3109 (5) Å0.20 × 0.10 × 0.10 mm
β = 107.671 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
3595 reflections with I > 2σ(I)
18010 measured reflectionsRint = 0.045
5600 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06512 restraints
wR(F2) = 0.170H-atom parameters constrained
S = 1.02Δρmax = 0.33 e Å3
5600 reflectionsΔρmin = 0.21 e Å3
397 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)
C10.5605 (5)1.1026 (3)0.0809 (3)0.1016 (16)
H1A0.49251.07420.09570.152*
H1B0.53081.11550.02410.152*
H1C0.58231.15290.11160.152*
C20.6797 (4)1.0481 (3)0.0986 (2)0.0819 (12)
H2A0.65860.99910.06470.098*
H2B0.74851.07770.08460.098*
C30.7296 (4)1.0218 (2)0.1857 (2)0.0600 (9)
C40.7612 (3)0.9620 (2)0.30584 (19)0.0464 (8)
C50.6770 (3)0.9653 (2)0.22757 (19)0.0493 (8)
C60.9700 (4)1.0424 (3)0.3756 (3)0.0843 (13)
H6A0.93971.05730.42050.126*
H6B1.01171.08930.35980.126*
H6C1.03160.99770.39130.126*
C70.7665 (3)0.91302 (19)0.37875 (18)0.0446 (7)
C80.5482 (3)0.96134 (19)0.37330 (17)0.0416 (7)
C90.6001 (3)1.0460 (2)0.39174 (18)0.0434 (7)
C100.6964 (3)1.0615 (2)0.46510 (19)0.0518 (8)
H100.72561.01880.50230.062*
C110.7483 (4)1.1396 (3)0.4827 (2)0.0675 (10)
H110.81121.15050.53200.081*
C120.7058 (4)1.2011 (2)0.4263 (3)0.0680 (11)
C130.6112 (4)1.1884 (2)0.3540 (2)0.0641 (10)
H130.58301.23150.31730.077*
C140.5585 (3)1.1101 (2)0.3366 (2)0.0508 (8)
H140.49461.10030.28750.061*
C150.4182 (3)0.9445 (2)0.34745 (18)0.0452 (7)
C160.3269 (3)1.0107 (2)0.3428 (2)0.0504 (8)
C170.3619 (3)0.8606 (3)0.3228 (2)0.0543 (9)
C200.6330 (3)0.8337 (2)0.44703 (19)0.0479 (8)
C210.7060 (3)0.7572 (2)0.44792 (19)0.0491 (8)
C220.7445 (4)0.7138 (2)0.3903 (2)0.0604 (9)
C230.8073 (5)0.6430 (3)0.4273 (3)0.0923 (14)
C180.1713 (16)0.7798 (7)0.2921 (11)0.077 (5)0.51
H18A0.20760.74510.25850.093*0.51
H18B0.18170.75220.34350.093*0.51
C190.0337 (14)0.7994 (15)0.2510 (13)0.159 (9)0.51
H19A0.00210.82890.28760.238*0.51
H19B0.01450.74910.23430.238*0.51
H19C0.02750.83320.20440.238*0.51
C240.8921 (8)0.5836 (4)0.3948 (5)0.089 (2)0.71
H24A0.89870.60300.34310.107*0.71
H24B0.97940.57930.43270.107*0.71
C250.8247 (9)0.5025 (4)0.3851 (6)0.127 (3)0.71
H25A0.81840.48450.43660.191*0.71
H25B0.87350.46260.36500.191*0.71
H25C0.73850.50790.34740.191*0.71
C260.7327 (5)0.7275 (3)0.5962 (2)0.0921 (14)
H26A0.64200.73560.59140.138*
H26B0.78110.77640.61860.138*
H26C0.76600.68120.63120.138*
Cl10.53576 (9)0.91015 (6)0.18601 (5)0.0620 (3)
Cl20.77506 (16)1.29995 (8)0.44793 (10)0.1232 (6)
Cl30.71509 (10)0.73843 (6)0.29021 (5)0.0700 (3)
N10.8404 (3)1.0541 (2)0.23522 (19)0.0693 (9)
N20.8587 (3)1.01616 (19)0.30722 (17)0.0596 (8)
N30.6432 (2)0.89762 (15)0.39096 (14)0.0414 (6)
N40.2531 (3)1.0622 (2)0.3401 (2)0.0723 (9)
N50.8081 (4)0.6418 (2)0.5053 (2)0.0992 (13)
N60.7463 (3)0.71124 (19)0.51636 (17)0.0667 (8)
O10.8667 (2)0.88843 (15)0.42578 (14)0.0596 (6)
O20.4232 (2)0.79961 (16)0.31937 (17)0.0697 (7)
O30.2329 (2)0.86236 (17)0.30416 (18)0.0849 (9)
O40.5658 (2)0.84529 (16)0.48997 (14)0.0683 (7)
C19'0.0535 (17)0.7807 (15)0.2940 (10)0.123 (8)0.49
H19D0.08840.76670.35040.184*0.49
H19E0.00250.73690.26580.184*0.49
H19F0.00410.83110.28850.184*0.49
C18'0.160 (2)0.7920 (11)0.2596 (11)0.099 (7)0.49
H18C0.12750.80400.20200.119*0.49
H18D0.21530.74300.26750.119*0.49
C24'0.8165 (13)0.5613 (7)0.3901 (10)0.064 (4)0.29
H24C0.75510.55820.33590.077*0.29
H24D0.79730.51700.42260.077*0.29
C25'0.9573 (15)0.5544 (12)0.3871 (14)0.114 (8)0.29
H25D0.99000.60860.38130.171*0.29
H25E0.95900.52060.34180.171*0.29
H25F1.01100.52960.43640.171*0.29
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.120 (4)0.103 (4)0.069 (3)0.023 (3)0.010 (3)0.017 (3)
C20.106 (3)0.090 (3)0.058 (2)0.009 (3)0.037 (2)0.017 (2)
C30.068 (2)0.067 (2)0.053 (2)0.007 (2)0.0323 (19)0.0092 (18)
C40.0394 (17)0.057 (2)0.0489 (18)0.0009 (15)0.0223 (14)0.0042 (15)
C50.0530 (19)0.054 (2)0.0459 (18)0.0040 (16)0.0219 (15)0.0022 (15)
C60.051 (2)0.114 (4)0.085 (3)0.023 (2)0.016 (2)0.016 (3)
C70.0445 (18)0.0460 (19)0.0444 (17)0.0024 (15)0.0150 (14)0.0006 (14)
C80.0415 (17)0.0505 (19)0.0354 (15)0.0011 (14)0.0156 (13)0.0014 (13)
C90.0433 (17)0.0491 (19)0.0426 (17)0.0016 (14)0.0202 (14)0.0013 (15)
C100.060 (2)0.055 (2)0.0413 (17)0.0009 (17)0.0167 (15)0.0000 (16)
C110.072 (2)0.072 (3)0.058 (2)0.015 (2)0.0188 (19)0.016 (2)
C120.081 (3)0.046 (2)0.087 (3)0.013 (2)0.041 (2)0.014 (2)
C130.074 (2)0.052 (2)0.070 (2)0.0044 (19)0.027 (2)0.0065 (19)
C140.0527 (19)0.052 (2)0.0491 (19)0.0011 (16)0.0172 (15)0.0026 (16)
C150.0468 (18)0.0497 (19)0.0441 (17)0.0018 (15)0.0213 (14)0.0034 (15)
C160.0428 (18)0.056 (2)0.056 (2)0.0021 (17)0.0206 (15)0.0040 (17)
C170.049 (2)0.066 (3)0.0500 (19)0.0080 (18)0.0183 (15)0.0022 (17)
C200.0542 (19)0.049 (2)0.0430 (17)0.0028 (16)0.0180 (15)0.0033 (15)
C210.056 (2)0.047 (2)0.0459 (18)0.0028 (16)0.0180 (15)0.0041 (15)
C220.074 (2)0.055 (2)0.052 (2)0.0086 (18)0.0182 (18)0.0001 (17)
C230.140 (4)0.065 (3)0.074 (3)0.039 (3)0.034 (3)0.001 (2)
C180.057 (7)0.081 (8)0.099 (11)0.032 (6)0.031 (7)0.017 (7)
C190.083 (10)0.159 (17)0.20 (2)0.053 (9)0.012 (13)0.026 (17)
C240.096 (7)0.066 (5)0.106 (6)0.006 (5)0.030 (6)0.002 (4)
C250.169 (9)0.088 (6)0.144 (8)0.016 (6)0.076 (6)0.025 (6)
C260.147 (4)0.079 (3)0.053 (2)0.015 (3)0.034 (3)0.016 (2)
Cl10.0643 (6)0.0700 (6)0.0486 (5)0.0069 (4)0.0125 (4)0.0022 (4)
Cl20.1617 (14)0.0646 (8)0.1425 (13)0.0441 (8)0.0452 (10)0.0271 (8)
Cl30.0878 (7)0.0770 (7)0.0490 (5)0.0122 (5)0.0263 (5)0.0028 (5)
N10.068 (2)0.085 (2)0.064 (2)0.0108 (18)0.0332 (17)0.0137 (18)
N20.0485 (16)0.075 (2)0.0597 (18)0.0044 (15)0.0225 (14)0.0099 (16)
N30.0416 (14)0.0435 (15)0.0420 (13)0.0004 (12)0.0172 (11)0.0034 (12)
N40.0542 (19)0.074 (2)0.094 (2)0.0064 (17)0.0310 (17)0.0015 (19)
N50.154 (4)0.066 (2)0.073 (2)0.041 (2)0.027 (2)0.0145 (19)
N60.098 (2)0.0534 (19)0.0487 (17)0.0085 (17)0.0219 (16)0.0094 (15)
O10.0428 (13)0.0702 (16)0.0600 (14)0.0027 (11)0.0069 (11)0.0128 (12)
O20.0635 (16)0.0582 (17)0.0903 (19)0.0093 (14)0.0278 (14)0.0143 (14)
O30.0497 (15)0.082 (2)0.120 (2)0.0187 (14)0.0214 (15)0.0215 (18)
O40.0842 (17)0.0763 (18)0.0597 (15)0.0154 (14)0.0445 (14)0.0172 (13)
C19'0.134 (18)0.129 (14)0.128 (14)0.063 (14)0.072 (12)0.039 (12)
C18'0.074 (10)0.100 (10)0.122 (15)0.028 (7)0.027 (10)0.012 (10)
C24'0.067 (10)0.043 (9)0.081 (10)0.003 (8)0.020 (9)0.007 (8)
C25'0.097 (15)0.124 (18)0.142 (17)0.032 (13)0.068 (13)0.024 (14)
Geometric parameters (Å, º) top
C1—C21.505 (6)C20—C211.460 (5)
C1—H1A0.9600C21—N61.353 (4)
C1—H1B0.9600C21—C221.381 (5)
C1—H1C0.9600C22—C231.382 (6)
C2—C31.499 (5)C22—Cl31.710 (4)
C2—H2A0.9700C23—N51.348 (5)
C2—H2B0.9700C23—C24'1.484 (9)
C3—N11.343 (5)C23—C241.542 (7)
C3—C51.387 (5)C18—C191.465 (10)
C4—N21.358 (4)C18—O31.475 (8)
C4—C51.383 (4)C18—H18A0.9700
C4—C71.476 (4)C18—H18B0.9700
C5—Cl11.716 (3)C19—H19A0.9600
C6—N21.465 (5)C19—H19B0.9600
C6—H6A0.9600C19—H19C0.9600
C6—H6B0.9600C24—C251.481 (7)
C6—H6C0.9600C24—H24A0.9700
C7—O11.202 (3)C24—H24B0.9700
C7—N31.423 (4)C25—H25A0.9600
C8—C151.356 (4)C25—H25B0.9600
C8—N31.415 (4)C25—H25C0.9600
C8—C91.475 (4)C26—N61.457 (5)
C9—C141.387 (4)C26—H26A0.9600
C9—C101.395 (4)C26—H26B0.9600
C10—C111.376 (5)C26—H26C0.9600
C10—H100.9300N1—N21.349 (4)
C11—C121.370 (6)N5—N61.345 (4)
C11—H110.9300O3—C18'1.458 (9)
C12—C131.367 (5)C19'—C18'1.456 (10)
C12—Cl21.752 (4)C19'—H19D0.9600
C13—C141.379 (5)C19'—H19E0.9600
C13—H130.9300C19'—H19F0.9600
C14—H140.9300C18'—H18C0.9700
C15—C161.436 (5)C18'—H18D0.9700
C15—C171.491 (5)C24'—C25'1.531 (10)
C16—N41.139 (4)C24'—H24C0.9700
C17—O21.196 (4)C24'—H24D0.9700
C17—O31.323 (4)C25'—H25D0.9600
C20—O41.197 (4)C25'—H25E0.9600
C20—N31.444 (4)C25'—H25F0.9600
C2—C1—H1A109.5C16—C15—C17116.7 (3)
C2—C1—H1B109.5N4—C16—C15178.5 (4)
H1A—C1—H1B109.5O2—C17—O3123.8 (3)
C2—C1—H1C109.5O2—C17—C15125.5 (3)
H1A—C1—H1C109.5O3—C17—C15110.7 (3)
H1B—C1—H1C109.5O4—C20—N3119.2 (3)
C3—C2—C1113.1 (3)O4—C20—C21123.3 (3)
C3—C2—H2A109.0N3—C20—C21117.5 (3)
C1—C2—H2A109.0N6—C21—C22105.6 (3)
C3—C2—H2B109.0N6—C21—C20120.0 (3)
C1—C2—H2B109.0C22—C21—C20134.3 (3)
H2A—C2—H2B107.8C21—C22—C23107.1 (3)
N1—C3—C5110.1 (3)C21—C22—Cl3127.6 (3)
N1—C3—C2120.5 (3)C22—C21—C20134.3 (3)
C5—C3—C2129.4 (4)C21—C22—C23107.1 (3)
N2—C4—C5105.2 (3)C21—C22—Cl3127.6 (3)
N2—C4—C7120.0 (3)C23—C22—Cl3125.2 (3)
C5—C4—C7134.7 (3)N5—C23—C22109.3 (3)
C4—C5—C3106.8 (3)N5—C23—C24'116.2 (8)
C4—C5—Cl1128.4 (3)C22—C23—C24'128.4 (8)
C3—C5—Cl1124.7 (3)N5—C23—C24122.2 (5)
N2—C6—H6A109.5C22—C23—C24127.2 (5)
N2—C6—H6B109.5C19—C18—O3102.4 (8)
H6A—C6—H6B109.5C19—C18—H18A111.3
N2—C6—H6C109.5O3—C18—H18A111.3
H6A—C6—H6C109.5C19—C18—H18B111.3
H6B—C6—H6C109.5O3—C18—H18B111.3
O1—C7—N3121.5 (3)H18A—C18—H18B109.2
O1—C7—C4123.4 (3)C25—C24—C23105.6 (6)
N3—C7—C4115.1 (3)C25—C24—H24A110.6
C15—C8—N3121.8 (3)C23—C24—H24A110.6
C15—C8—C9122.7 (3)C25—C24—H24B110.6
N3—C8—C9115.3 (2)C23—C24—H24B110.6
C14—C9—C10119.2 (3)H24A—C24—H24B108.7
C14—C9—C8121.5 (3)N6—C26—H26A109.5
C10—C9—C8119.3 (3)N6—C26—H26B109.5
C11—C10—C9120.3 (3)H26A—C26—H26B109.5
C11—C10—H10119.9N6—C26—H26C109.5
C9—C10—H10119.9H26A—C26—H26C109.5
C12—C11—C10118.8 (3)H26B—C26—H26C109.5
C12—C11—H11120.6C3—N1—N2105.4 (3)
C10—C11—H11120.6N1—N2—C4112.4 (3)
C13—C12—C11122.5 (3)N1—N2—C6118.0 (3)
C13—C12—Cl2118.8 (3)C4—N2—C6129.4 (3)
C11—C12—Cl2118.7 (3)C8—N3—C7118.8 (2)
C12—C13—C14118.6 (4)C8—N3—C20117.9 (2)
C12—C13—H13120.7C7—N3—C20119.2 (2)
C14—C13—H13120.7N6—N5—C23106.1 (3)
C13—C14—C9120.6 (3)N5—N6—C21111.9 (3)
C13—C14—H14119.7N5—N6—C26118.7 (3)
C9—C14—H14119.7C21—N6—C26129.4 (3)
C8—C15—C16119.0 (3)C17—O3—C18'117.5 (10)
C8—C15—C17124.3 (3)C17—O3—C18114.0 (8)
C16—C15—C17116.7 (3)C18'—C19'—H19D109.5
N4—C16—C15178.5 (4)C18'—C19'—H19E109.5
O2—C17—O3123.8 (3)H19D—C19'—H19E109.5
O2—C17—C15125.5 (3)C18'—C19'—H19F109.5
O3—C17—C15110.7 (3)H19D—C19'—H19F109.5
O4—C20—N3119.2 (3)H19E—C19'—H19F109.5
O4—C20—C21123.3 (3)C19'—C18'—O3103.9 (9)
N3—C20—C21117.5 (3)C19'—C18'—H18C111.0
N6—C21—C22105.6 (3)O3—C18'—H18C111.0
N6—C21—C20120.0 (3)C19'—C18'—H18D111.0
C22—C21—C20134.3 (3)O3—C18'—H18D111.0
C21—C22—C23107.1 (3)H18C—C18'—H18D109.0
C21—C22—Cl3127.6 (3)C23—C24'—C25'106.0 (8)
C10—C11—H11120.6C23—C24'—H24C110.5
C13—C12—C11122.5 (3)C25'—C24'—H24C110.5
C13—C12—Cl2118.8 (3)C23—C24'—H24D110.5
C11—C12—Cl2118.7 (3)C25'—C24'—H24D110.5
C12—C13—C14118.6 (4)H24C—C24'—H24D108.7
C12—C13—H13120.7C24'—C25'—H25D109.5
C14—C13—H13120.7C24'—C25'—H25E109.5
C13—C14—C9120.6 (3)H25D—C25'—H25E109.5
C13—C14—H14119.7C24'—C25'—H25F109.5
C9—C14—H14119.7H25D—C25'—H25F109.5
C8—C15—C16119.0 (3)H25E—C25'—H25F109.5
C8—C15—C17124.3 (3)
C1—C2—C3—N1107.3 (5)Cl3—C22—C23—C24'26.2 (10)
C1—C2—C3—C572.6 (6)C21—C22—C23—C24166.6 (5)
N2—C4—C5—C30.2 (4)Cl3—C22—C23—C2416.2 (8)
C7—C4—C5—C3176.8 (3)N5—C23—C24—C2576.6 (8)
N2—C4—C5—Cl1178.8 (2)C22—C23—C24—C25118.3 (7)
C7—C4—C5—Cl11.8 (6)C24'—C23—C24—C2512.9 (14)
N1—C3—C5—C41.2 (4)C5—C3—N1—N21.6 (4)
C2—C3—C5—C4178.9 (4)C2—C3—N1—N2178.4 (3)
N1—C3—C5—Cl1179.8 (3)C3—N1—N2—C41.6 (4)
C2—C3—C5—Cl10.2 (6)C3—N1—N2—C6176.7 (3)
N2—C4—C7—O133.8 (5)C5—C4—N2—N10.8 (4)
C5—C4—C7—O1142.9 (4)C7—C4—N2—N1178.4 (3)
N2—C4—C7—N3145.1 (3)C5—C4—N2—C6175.3 (4)
C5—C4—C7—N338.2 (5)C7—C4—N2—C67.1 (5)
C15—C8—C9—C1451.9 (4)C15—C8—N3—C7149.4 (3)
N3—C8—C9—C14133.3 (3)C9—C8—N3—C735.7 (4)
C15—C8—C9—C10130.3 (3)C15—C8—N3—C2053.3 (4)
N3—C8—C9—C1044.5 (4)C9—C8—N3—C20121.6 (3)
C14—C9—C10—C110.7 (5)O1—C7—N3—C8140.0 (3)
C8—C9—C10—C11178.5 (3)C4—C7—N3—C838.9 (4)
C9—C10—C11—C121.4 (5)O1—C7—N3—C2017.0 (4)
C10—C11—C12—C131.7 (6)C4—C7—N3—C20164.1 (3)
C10—C11—C12—Cl2178.5 (3)O4—C20—N3—C816.6 (4)
C11—C12—C13—C141.3 (6)C21—C20—N3—C8163.2 (3)
Cl2—C12—C13—C14178.9 (3)O4—C20—N3—C7140.6 (3)
C12—C13—C14—C90.5 (5)C21—C20—N3—C739.6 (4)
C10—C9—C14—C130.2 (5)C22—C23—N5—N60.0 (6)
C8—C9—C14—C13178.0 (3)C24'—C23—N5—N6154.8 (7)
N3—C8—C15—C16170.3 (3)C24—C23—N5—N6167.5 (5)
C9—C8—C15—C164.3 (4)C23—N5—N6—C210.2 (5)
N3—C8—C15—C179.9 (5)C23—N5—N6—C26179.5 (4)
C9—C8—C15—C17175.6 (3)C22—C21—N6—N50.2 (4)
C8—C15—C17—O23.5 (5)C20—C21—N6—N5178.0 (3)
C16—C15—C17—O2176.4 (3)C22—C21—N6—C26179.5 (4)
C8—C15—C17—O3177.0 (3)C20—C21—N6—C262.8 (6)
C16—C15—C17—O33.1 (4)O2—C17—O3—C18'14.9 (10)
O4—C20—C21—N627.8 (5)C15—C17—O3—C18'164.7 (9)
N3—C20—C21—N6152.4 (3)O2—C17—O3—C189.9 (9)
O4—C20—C21—C22149.1 (4)C15—C17—O3—C18170.5 (8)
N3—C20—C21—C2230.7 (5)C19—C18—O3—C17164.7 (12)
N6—C21—C22—C230.2 (4)C19—C18—O3—C18'60 (4)
C20—C21—C22—C23177.4 (4)C17—O3—C18'—C19'142.5 (12)
N6—C21—C22—Cl3176.9 (3)C18—O3—C18'—C19'56 (4)
C20—C21—C22—Cl30.3 (6)N5—C23—C24'—C25'103.8 (14)
C21—C22—C23—N50.1 (6)C22—C23—C24'—C25'107.0 (14)
Cl3—C22—C23—N5177.1 (3)C24—C23—C24'—C25'5.7 (12)
C21—C22—C23—C24'151.0 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.932.593.420 (5)149
Symmetry code: (i) x+1, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC26H25Cl3N6O4
Mr591.87
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)10.7277 (3), 16.1476 (5), 17.3109 (5)
β (°) 107.671 (2)
V3)2857.21 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.36
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
18010, 5600, 3595
Rint0.045
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.065, 0.170, 1.02
No. of reflections5600
No. of parameters397
No. of restraints12
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.33, 0.21

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O2i0.932.593.420 (5)148.7
Symmetry code: (i) x+1, y+1/2, z+1/2.
 

Acknowledgements

We thank the Hubei Normal University and the Hunan Provincial Natural Science Fund of China for support.

References

First citationBruker (1997). SMART. Bruker AXS Inc., Madison,Wisconsin, USA.
First citationBruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCreagh, D. C & Hubbell, J. H. (1992). International Tables for Crystallography, Vol. C, pp. 200–206. Dordrecht: Kluwer.
First citationHeller, D., Drexler, H. J., You, J. & Zhang, S. L. (2004). WO Patent 011414.
First citationIbers, J. A. & Hamilton, W. C. (1964). Acta Cryst. 17, 781–782.  CrossRef IUCr Journals Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS 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