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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Amitraz

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea, and bTest and Analytical Laboratory, Korea Food and Drug Administration, 123-7 Yongdang-dong, Busan 608-829, Republic of Korea
*Correspondence e-mail: jekim@gnu.ac.kr, thkim@gnu.ac.kr

(Received 8 July 2013; accepted 17 July 2013; online 24 July 2013)

In the asymmetric unit of the title compound {systematic name: N′-(2,4-di­methyl­phen­yl)-N-[N-(2,4-di­methyl­phen­yl)carbox­imido­yl]-N-methyl­methanimidamide}, C19H23N3, which is a formamidine pesticide, there are two independent and conformationally similar mol­ecules, with the dihedral angle between the mean planes of the 2,4-di­methylbenzene rings in each mol­ecule being 41.63 (6) and 42.09 (5)°. The crystal structure is stabilized by a C—H⋯N hydrogen bond, as well as weak inter­molecular C—H⋯π and ππ inter­actions [ring centroid separation = 3.7409 (15) Å], giving one-dimensional chains extending down the b direction.

Related literature

For the toxicity and insecticidal properties of the title compound, see: Del Pino et al. (2013[Del Pino, J., Martinez, M. A., Castellano, V., Ramos, E., Martinez-Larranaga, M. R. & Anadon, A. (2013). Toxicology, 308, 88-95.]); Hollingworth (1976[Hollingworth, R. M. (1976). Environ. Health Perspect. 14, 57-69.]). For a related crystal structure, see: Peoples et al. (2012[Peoples, B. C., De la Vega, G., Valdebenito, C., Quijada, R., Ibañez, A., Valderrama, M. & Rojas, R. (2012). J. Organomet. Chem. 700, 147-153.]).

[Scheme 1]

Experimental

Crystal data
  • C19H23N3

  • Mr = 293.40

  • Monoclinic, P 21 /c

  • a = 11.9362 (11) Å

  • b = 7.5110 (7) Å

  • c = 37.514 (3) Å

  • β = 91.650 (2)°

  • V = 3361.9 (5) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 173 K

  • 0.40 × 0.40 × 0.40 mm

Data collection
  • Bruker APEXII CCD-detecto diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.973

  • 18091 measured reflections

  • 6593 independent reflections

  • 3615 reflections with I > 2σ(I)

  • Rint = 0.058

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.182

  • S = 0.98

  • 6593 reflections

  • 407 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.22 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg4 are the centroids of the C2–C8 and C31–C38 rings.

D—H⋯A D—H H⋯A DA D—H⋯A
C29—H29C⋯N3i 0.98 2.49 3.334 (4) 144
C17—H17ACg4i 0.98 2.92 3.806 (3) 151
C24—H24ACg1ii 0.98 2.85 3.828 (3) 175
C33—H33BCg4iii 0.98 2.88 3.625 (3) 134
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, 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

The title compound (C19H23N3) (common name amitraz) is one of the most widely used formamidine acaricide/insecticide in veterinary medicine and agriculture for use on ectoparasites (Del Pino et al., 2013; Hollingworth, 1976). However, until now its crystal structure has not been reported.

In this compound (Scheme 1, Fig. 1), there are two independent and conformationally similar molecules (A and B) in the asymmetric unit, with the dihedral angle between the mean planes of the 2,4-dimethylphenyl rings in each of 41.63 (6) and 42.09 (5)°, respectively. All bond lengths and bond angles are normal and comparable to those observed in the crystal structures of a similar compound (Peoples et al., 2012).

In the crystal structure (Fig. 2), an intermolecular C—H··· N hydrogen bond between a methyl C29 H atom and the N3 acceptor of the B molecule, as well as weak intermolecular C—H···π interactions (Table 1), are present. There is also a ππ interaction between one of the A-molecule 2,4-dimethylphenyl rings (defined by atoms C2–C8) [ring centroid separation 3.7409 (15) Å].

Related literature top

For the toxicity and insecticidal properties of the title compound, see: Del Pino et al. (2013); Hollingworth (1976). For a related crystal structure, see: Peoples et al. (2012).

Experimental top

The title compound was purchased from the Dr Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH2Cl2 gave single crystals suitable for X-ray analysis.

Refinement top

All H atoms were positioned geometrically and refined using a riding model with C—H = 0.95 Å, Uiso = 1.2Ueq(C) for Csp2—H and C—H = 0.98 Å, Uiso = 1.5Ueq(C) for CH3 groups.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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, with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
[Figure 2] Fig. 2. Crystal packing of the title compound in the unit cell, with weak intermolecular C—H···N hydrogen bonds shown as dashed lines.
N'-(2,4-Dimethylphenyl)-N-[N-(2,4-dimethylphenyl)carboximidoyl]-N-methylmethanimidamide top
Crystal data top
C19H23N3F(000) = 1264
Mr = 293.40Dx = 1.159 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2173 reflections
a = 11.9362 (11) Åθ = 2.7–23.1°
b = 7.5110 (7) ŵ = 0.07 mm1
c = 37.514 (3) ÅT = 173 K
β = 91.650 (2)°Block, colourless
V = 3361.9 (5) Å30.40 × 0.40 × 0.40 mm
Z = 8
Data collection top
Bruker APEXII CCD-detecto
diffractometer
6593 independent reflections
Radiation source: fine-focus sealed tube3615 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.058
ϕ and ω scansθmax = 26.0°, θmin = 1.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
h = 1414
Tmin = 0.973, Tmax = 0.973k = 99
18091 measured reflectionsl = 4636
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)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0907P)2]
where P = (Fo2 + 2Fc2)/3
6593 reflections(Δ/σ)max = 0.001
407 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.22 e Å3
Crystal data top
C19H23N3V = 3361.9 (5) Å3
Mr = 293.40Z = 8
Monoclinic, P21/cMo Kα radiation
a = 11.9362 (11) ŵ = 0.07 mm1
b = 7.5110 (7) ÅT = 173 K
c = 37.514 (3) Å0.40 × 0.40 × 0.40 mm
β = 91.650 (2)°
Data collection top
Bruker APEXII CCD-detecto
diffractometer
6593 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2006)
3615 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.973Rint = 0.058
18091 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.182H-atom parameters constrained
S = 0.98Δρmax = 0.26 e Å3
6593 reflectionsΔρmin = 0.22 e Å3
407 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
N10.22503 (17)0.8667 (3)0.54029 (6)0.0318 (5)
N20.07334 (17)0.8469 (3)0.57777 (5)0.0303 (5)
N30.06461 (17)0.8046 (3)0.61902 (5)0.0316 (5)
N40.02203 (18)0.7540 (3)0.88836 (6)0.0349 (6)
N50.16767 (17)0.7179 (3)0.84902 (6)0.0335 (6)
N60.30082 (18)0.6971 (3)0.80512 (6)0.0342 (6)
C10.3145 (2)0.6882 (4)0.48038 (7)0.0393 (7)
H1A0.28080.78460.46610.059*
H1B0.25510.61750.49100.059*
H1C0.35910.61180.46510.059*
C20.3887 (2)0.7661 (3)0.50947 (7)0.0306 (6)
C30.5052 (2)0.7534 (3)0.50820 (7)0.0344 (7)
H30.53670.69110.48890.041*
C40.5770 (2)0.8273 (3)0.53382 (7)0.0326 (7)
C50.7027 (2)0.8131 (4)0.53071 (8)0.0440 (8)
H5A0.72310.83790.50610.066*
H5B0.72710.69270.53730.066*
H5C0.73940.89970.54670.066*
C60.5292 (2)0.9178 (3)0.56183 (7)0.0349 (7)
H60.57630.97030.57980.042*
C70.4140 (2)0.9327 (3)0.56400 (7)0.0322 (6)
H70.38290.99700.58310.039*
C80.3435 (2)0.8542 (3)0.53838 (7)0.0288 (6)
C90.1853 (2)0.8345 (3)0.57073 (7)0.0304 (6)
H90.23560.80020.58960.036*
C100.0063 (2)0.9115 (4)0.55032 (7)0.0377 (7)
H10A0.05100.81150.54100.057*
H10B0.03480.96600.53090.057*
H10C0.05591.00020.56070.057*
C110.0382 (2)0.8003 (3)0.61073 (7)0.0317 (6)
H110.09240.76310.62820.038*
C120.0910 (2)0.7724 (3)0.65503 (7)0.0288 (6)
C130.1938 (2)0.6914 (3)0.66229 (7)0.0320 (6)
C140.2710 (2)0.6305 (4)0.63229 (7)0.0417 (7)
H14A0.32970.55430.64180.063*
H14B0.22810.56310.61490.063*
H14C0.30540.73430.62060.063*
C150.2228 (2)0.6670 (4)0.69766 (7)0.0354 (7)
H150.29250.61220.70250.042*
C160.1540 (2)0.7193 (4)0.72608 (7)0.0372 (7)
C170.1871 (3)0.6882 (4)0.76443 (7)0.0497 (8)
H17A0.25290.61020.76470.075*
H17B0.20500.80240.77550.075*
H17C0.12480.63190.77770.075*
C180.0534 (2)0.8020 (4)0.71861 (7)0.0393 (7)
H180.00500.84020.73770.047*
C190.0226 (2)0.8295 (4)0.68357 (7)0.0366 (7)
H190.04600.88810.67900.044*
C200.0414 (3)0.9162 (4)0.95372 (7)0.0493 (8)
H20A0.07740.98720.97210.074*
H20B0.02040.98430.94380.074*
H20C0.01210.80580.96440.074*
C210.1258 (2)0.8719 (3)0.92448 (7)0.0325 (6)
C220.2386 (2)0.9098 (4)0.92838 (7)0.0367 (7)
H220.26120.96120.95020.044*
C230.3199 (2)0.8764 (4)0.90212 (7)0.0345 (7)
C240.4417 (2)0.9186 (4)0.90765 (8)0.0463 (8)
H24A0.44761.03090.92080.069*
H24B0.47570.82260.92130.069*
H24C0.48090.92970.88440.069*
C250.2856 (2)0.7988 (4)0.87098 (7)0.0395 (7)
H250.33910.77340.85240.047*
C260.1744 (2)0.7576 (4)0.86650 (7)0.0386 (7)
H260.15300.70060.84510.046*
C270.0928 (2)0.7972 (4)0.89247 (7)0.0322 (6)
C280.0609 (2)0.7700 (4)0.85751 (7)0.0343 (7)
H280.01420.82050.83930.041*
C290.2435 (2)0.6444 (4)0.87668 (7)0.0399 (7)
H29A0.26360.73780.89400.060*
H29B0.31140.59970.86570.060*
H29C0.20600.54660.88890.060*
C300.2031 (2)0.7375 (3)0.81483 (7)0.0323 (6)
H300.15160.78410.79740.039*
C310.3252 (2)0.7255 (3)0.76890 (7)0.0311 (6)
C320.4296 (2)0.8009 (3)0.76116 (7)0.0327 (7)
C330.5113 (2)0.8437 (4)0.79118 (7)0.0435 (8)
H33A0.47700.92800.80750.065*
H33B0.57900.89680.78150.065*
H33C0.53130.73420.80410.065*
C340.4541 (2)0.8329 (4)0.72587 (8)0.0398 (7)
H340.52380.88670.72070.048*
C350.3809 (3)0.7896 (4)0.69786 (8)0.0422 (8)
C360.4117 (3)0.8261 (5)0.65963 (8)0.0645 (10)
H36A0.39740.71950.64520.097*
H36B0.49140.85720.65880.097*
H36C0.36640.92510.65020.097*
C370.2804 (2)0.7109 (4)0.70560 (8)0.0420 (8)
H370.22980.67790.68670.050*
C380.2520 (2)0.6791 (4)0.74065 (7)0.0384 (7)
H380.18210.62520.74550.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0276 (13)0.0354 (13)0.0327 (13)0.0026 (10)0.0062 (10)0.0000 (10)
N20.0257 (12)0.0392 (13)0.0261 (13)0.0016 (10)0.0039 (10)0.0012 (10)
N30.0300 (13)0.0350 (13)0.0300 (13)0.0006 (10)0.0066 (10)0.0023 (10)
N40.0367 (14)0.0377 (13)0.0304 (13)0.0014 (11)0.0025 (11)0.0006 (11)
N50.0275 (13)0.0385 (13)0.0344 (14)0.0012 (10)0.0009 (10)0.0061 (11)
N60.0298 (13)0.0364 (14)0.0366 (14)0.0012 (10)0.0025 (11)0.0031 (11)
C10.0416 (17)0.0466 (18)0.0300 (16)0.0029 (14)0.0044 (13)0.0033 (13)
C20.0316 (16)0.0324 (15)0.0280 (15)0.0010 (12)0.0048 (12)0.0042 (12)
C30.0379 (17)0.0352 (16)0.0307 (16)0.0013 (13)0.0089 (13)0.0028 (13)
C40.0290 (15)0.0313 (15)0.0376 (17)0.0014 (12)0.0033 (12)0.0069 (13)
C50.0303 (16)0.0447 (18)0.057 (2)0.0010 (14)0.0034 (14)0.0034 (15)
C60.0358 (16)0.0348 (16)0.0342 (17)0.0048 (13)0.0006 (13)0.0033 (13)
C70.0353 (16)0.0362 (16)0.0253 (15)0.0022 (13)0.0062 (12)0.0002 (12)
C80.0272 (14)0.0312 (15)0.0283 (16)0.0002 (12)0.0051 (12)0.0035 (12)
C90.0251 (15)0.0335 (16)0.0328 (16)0.0007 (12)0.0033 (12)0.0010 (12)
C100.0311 (16)0.0494 (18)0.0326 (16)0.0064 (13)0.0002 (12)0.0049 (14)
C110.0290 (16)0.0383 (16)0.0281 (15)0.0026 (12)0.0037 (12)0.0004 (12)
C120.0237 (14)0.0313 (15)0.0317 (16)0.0040 (12)0.0039 (11)0.0046 (12)
C130.0265 (15)0.0297 (15)0.0399 (17)0.0041 (12)0.0038 (12)0.0038 (12)
C140.0350 (17)0.0422 (18)0.0478 (19)0.0071 (13)0.0009 (14)0.0069 (14)
C150.0310 (16)0.0327 (16)0.0428 (18)0.0001 (12)0.0095 (13)0.0068 (13)
C160.0416 (17)0.0339 (16)0.0366 (17)0.0085 (14)0.0106 (14)0.0065 (13)
C170.060 (2)0.053 (2)0.0377 (18)0.0053 (16)0.0165 (15)0.0080 (15)
C180.0379 (17)0.0470 (18)0.0330 (17)0.0050 (14)0.0017 (13)0.0020 (13)
C190.0265 (15)0.0461 (18)0.0374 (17)0.0001 (13)0.0061 (13)0.0016 (14)
C200.059 (2)0.050 (2)0.0384 (19)0.0076 (16)0.0076 (15)0.0096 (15)
C210.0400 (17)0.0324 (15)0.0250 (15)0.0004 (13)0.0010 (12)0.0006 (12)
C220.0463 (18)0.0322 (16)0.0318 (16)0.0014 (13)0.0066 (14)0.0011 (13)
C230.0370 (17)0.0328 (16)0.0340 (17)0.0002 (13)0.0037 (13)0.0068 (13)
C240.0432 (19)0.0472 (19)0.049 (2)0.0020 (15)0.0092 (15)0.0045 (15)
C250.0348 (17)0.0534 (19)0.0304 (17)0.0037 (14)0.0001 (13)0.0006 (14)
C260.0363 (17)0.0537 (19)0.0259 (16)0.0008 (14)0.0055 (13)0.0052 (13)
C270.0321 (16)0.0328 (15)0.0319 (16)0.0014 (12)0.0022 (12)0.0045 (12)
C280.0293 (16)0.0348 (16)0.0385 (17)0.0005 (12)0.0029 (13)0.0028 (13)
C290.0317 (16)0.0450 (18)0.0426 (18)0.0012 (13)0.0034 (13)0.0101 (14)
C300.0323 (16)0.0323 (16)0.0322 (16)0.0047 (12)0.0019 (12)0.0022 (12)
C310.0273 (15)0.0294 (15)0.0364 (17)0.0040 (12)0.0009 (12)0.0000 (12)
C320.0313 (16)0.0284 (15)0.0385 (17)0.0042 (12)0.0012 (13)0.0026 (12)
C330.0327 (17)0.0488 (19)0.049 (2)0.0061 (14)0.0013 (14)0.0027 (15)
C340.0400 (18)0.0331 (16)0.0470 (19)0.0034 (13)0.0109 (15)0.0037 (14)
C350.054 (2)0.0390 (17)0.0339 (18)0.0128 (15)0.0068 (15)0.0006 (14)
C360.090 (3)0.066 (2)0.038 (2)0.018 (2)0.0131 (18)0.0051 (17)
C370.0427 (18)0.0452 (18)0.0375 (18)0.0141 (15)0.0092 (14)0.0054 (14)
C380.0281 (16)0.0424 (17)0.0446 (19)0.0030 (13)0.0011 (13)0.0046 (14)
Geometric parameters (Å, º) top
N1—C91.272 (3)C16—C171.521 (3)
N1—C81.421 (3)C17—H17A0.9800
N2—C111.363 (3)C17—H17B0.9800
N2—C91.372 (3)C17—H17C0.9800
N2—C101.463 (3)C18—C191.391 (3)
N3—C111.275 (3)C18—H180.9500
N3—C121.417 (3)C19—H190.9500
N4—C281.265 (3)C20—C211.506 (4)
N4—C271.422 (3)C20—H20A0.9800
N5—C301.370 (3)C20—H20B0.9800
N5—C281.379 (3)C20—H20C0.9800
N5—C291.465 (3)C21—C221.388 (4)
N6—C301.269 (3)C21—C271.393 (3)
N6—C311.414 (3)C22—C231.385 (4)
C1—C21.504 (3)C22—H220.9500
C1—H1A0.9800C23—C251.378 (4)
C1—H1B0.9800C23—C241.508 (4)
C1—H1C0.9800C24—H24A0.9800
C2—C81.393 (3)C24—H24B0.9800
C2—C31.396 (3)C24—H24C0.9800
C3—C41.385 (4)C25—C261.378 (4)
C3—H30.9500C25—H250.9500
C4—C61.388 (4)C26—C271.389 (3)
C4—C51.512 (3)C26—H260.9500
C5—H5A0.9800C28—H280.9500
C5—H5B0.9800C29—H29A0.9800
C5—H5C0.9800C29—H29B0.9800
C6—C71.384 (4)C29—H29C0.9800
C6—H60.9500C30—H300.9500
C7—C81.390 (3)C31—C381.399 (4)
C7—H70.9500C31—C321.406 (4)
C9—H90.9500C32—C341.385 (4)
C10—H10A0.9800C32—C331.503 (4)
C10—H10B0.9800C33—H33A0.9800
C10—H10C0.9800C33—H33B0.9800
C11—H110.9500C33—H33C0.9800
C12—C191.395 (4)C34—C351.386 (4)
C12—C131.404 (3)C34—H340.9500
C13—C151.393 (3)C35—C371.377 (4)
C13—C141.505 (4)C35—C361.516 (4)
C14—H14A0.9800C36—H36A0.9800
C14—H14B0.9800C36—H36B0.9800
C14—H14C0.9800C36—H36C0.9800
C15—C161.384 (4)C37—C381.388 (4)
C15—H150.9500C37—H370.9500
C16—C181.388 (4)C38—H380.9500
C9—N1—C8115.5 (2)C16—C18—H18119.6
C11—N2—C9118.9 (2)C19—C18—H18119.6
C11—N2—C10120.9 (2)C18—C19—C12121.0 (3)
C9—N2—C10120.2 (2)C18—C19—H19119.5
C11—N3—C12118.1 (2)C12—C19—H19119.5
C28—N4—C27117.3 (2)C21—C20—H20A109.5
C30—N5—C28119.9 (2)C21—C20—H20B109.5
C30—N5—C29120.2 (2)H20A—C20—H20B109.5
C28—N5—C29119.9 (2)C21—C20—H20C109.5
C30—N6—C31117.1 (2)H20A—C20—H20C109.5
C2—C1—H1A109.5H20B—C20—H20C109.5
C2—C1—H1B109.5C22—C21—C27118.2 (3)
H1A—C1—H1B109.5C22—C21—C20120.6 (2)
C2—C1—H1C109.5C27—C21—C20121.1 (3)
H1A—C1—H1C109.5C23—C22—C21123.3 (3)
H1B—C1—H1C109.5C23—C22—H22118.3
C8—C2—C3117.9 (3)C21—C22—H22118.3
C8—C2—C1121.1 (2)C25—C23—C22117.4 (3)
C3—C2—C1121.0 (2)C25—C23—C24121.1 (3)
C4—C3—C2123.1 (2)C22—C23—C24121.5 (3)
C4—C3—H3118.5C23—C24—H24A109.5
C2—C3—H3118.5C23—C24—H24B109.5
C3—C4—C6117.5 (2)H24A—C24—H24B109.5
C3—C4—C5120.9 (2)C23—C24—H24C109.5
C6—C4—C5121.5 (3)H24A—C24—H24C109.5
C4—C5—H5A109.5H24B—C24—H24C109.5
C4—C5—H5B109.5C26—C25—C23120.6 (3)
H5A—C5—H5B109.5C26—C25—H25119.7
C4—C5—H5C109.5C23—C25—H25119.7
H5A—C5—H5C109.5C25—C26—C27121.6 (3)
H5B—C5—H5C109.5C25—C26—H26119.2
C7—C6—C4121.0 (3)C27—C26—H26119.2
C7—C6—H6119.5C26—C27—C21118.8 (2)
C4—C6—H6119.5C26—C27—N4122.2 (2)
C6—C7—C8120.5 (2)C21—C27—N4118.9 (2)
C6—C7—H7119.7N4—C28—N5123.4 (3)
C8—C7—H7119.7N4—C28—H28118.3
C7—C8—C2120.0 (2)N5—C28—H28118.3
C7—C8—N1121.4 (2)N5—C29—H29A109.5
C2—C8—N1118.6 (2)N5—C29—H29B109.5
N1—C9—N2123.4 (3)H29A—C29—H29B109.5
N1—C9—H9118.3N5—C29—H29C109.5
N2—C9—H9118.3H29A—C29—H29C109.5
N2—C10—H10A109.5H29B—C29—H29C109.5
N2—C10—H10B109.5N6—C30—N5123.6 (3)
H10A—C10—H10B109.5N6—C30—H30118.2
N2—C10—H10C109.5N5—C30—H30118.2
H10A—C10—H10C109.5C38—C31—C32118.8 (3)
H10B—C10—H10C109.5C38—C31—N6123.3 (2)
N3—C11—N2122.6 (2)C32—C31—N6117.9 (2)
N3—C11—H11118.7C34—C32—C31118.7 (3)
N2—C11—H11118.7C34—C32—C33121.9 (3)
C19—C12—C13118.7 (2)C31—C32—C33119.4 (2)
C19—C12—N3122.5 (2)C32—C33—H33A109.5
C13—C12—N3118.6 (2)C32—C33—H33B109.5
C15—C13—C12119.0 (3)H33A—C33—H33B109.5
C15—C13—C14120.6 (2)C32—C33—H33C109.5
C12—C13—C14120.4 (2)H33A—C33—H33C109.5
C13—C14—H14A109.5H33B—C33—H33C109.5
C13—C14—H14B109.5C32—C34—C35122.5 (3)
H14A—C14—H14B109.5C32—C34—H34118.7
C13—C14—H14C109.5C35—C34—H34118.7
H14A—C14—H14C109.5C37—C35—C34118.4 (3)
H14B—C14—H14C109.5C37—C35—C36120.9 (3)
C16—C15—C13122.6 (3)C34—C35—C36120.7 (3)
C16—C15—H15118.7C35—C36—H36A109.5
C13—C15—H15118.7C35—C36—H36B109.5
C15—C16—C18118.0 (3)H36A—C36—H36B109.5
C15—C16—C17121.4 (3)C35—C36—H36C109.5
C18—C16—C17120.6 (3)H36A—C36—H36C109.5
C16—C17—H17A109.5H36B—C36—H36C109.5
C16—C17—H17B109.5C35—C37—C38120.8 (3)
H17A—C17—H17B109.5C35—C37—H37119.6
C16—C17—H17C109.5C38—C37—H37119.6
H17A—C17—H17C109.5C37—C38—C31120.7 (3)
H17B—C17—H17C109.5C37—C38—H38119.7
C16—C18—C19120.7 (3)C31—C38—H38119.7
C8—C2—C3—C41.4 (4)C27—C21—C22—C230.2 (4)
C1—C2—C3—C4178.2 (2)C20—C21—C22—C23178.3 (3)
C2—C3—C4—C60.1 (4)C21—C22—C23—C251.2 (4)
C2—C3—C4—C5178.6 (2)C21—C22—C23—C24179.6 (3)
C3—C4—C6—C70.2 (4)C22—C23—C25—C260.3 (4)
C5—C4—C6—C7178.7 (2)C24—C23—C25—C26178.7 (3)
C4—C6—C7—C81.1 (4)C23—C25—C26—C272.0 (4)
C6—C7—C8—C22.7 (4)C25—C26—C27—C213.4 (4)
C6—C7—C8—N1179.4 (2)C25—C26—C27—N4179.4 (3)
C3—C2—C8—C72.7 (4)C22—C21—C27—C262.5 (4)
C1—C2—C8—C7176.8 (2)C20—C21—C27—C26179.5 (3)
C3—C2—C8—N1179.3 (2)C22—C21—C27—N4178.6 (2)
C1—C2—C8—N11.1 (4)C20—C21—C27—N43.3 (4)
C9—N1—C8—C746.5 (3)C28—N4—C27—C2637.4 (4)
C9—N1—C8—C2135.5 (3)C28—N4—C27—C21146.6 (3)
C8—N1—C9—N2177.4 (2)C27—N4—C28—N5174.0 (2)
C11—N2—C9—N1176.4 (2)C30—N5—C28—N4179.1 (2)
C10—N2—C9—N14.4 (4)C29—N5—C28—N41.8 (4)
C12—N3—C11—N2173.2 (2)C31—N6—C30—N5179.8 (2)
C9—N2—C11—N3178.5 (2)C28—N5—C30—N6178.2 (2)
C10—N2—C11—N32.3 (4)C29—N5—C30—N60.9 (4)
C11—N3—C12—C1935.7 (4)C30—N6—C31—C3844.3 (4)
C11—N3—C12—C13149.0 (2)C30—N6—C31—C32137.1 (3)
C19—C12—C13—C151.5 (4)C38—C31—C32—C342.6 (4)
N3—C12—C13—C15177.0 (2)N6—C31—C32—C34178.8 (2)
C19—C12—C13—C14179.0 (2)C38—C31—C32—C33177.2 (2)
N3—C12—C13—C143.6 (4)N6—C31—C32—C331.5 (4)
C12—C13—C15—C160.1 (4)C31—C32—C34—C351.6 (4)
C14—C13—C15—C16179.4 (2)C33—C32—C34—C35178.2 (3)
C13—C15—C16—C181.2 (4)C32—C34—C35—C370.4 (4)
C13—C15—C16—C17179.0 (2)C32—C34—C35—C36179.6 (3)
C15—C16—C18—C190.6 (4)C34—C35—C37—C381.3 (4)
C17—C16—C18—C19179.6 (3)C36—C35—C37—C38179.4 (3)
C16—C18—C19—C121.0 (4)C35—C37—C38—C310.3 (4)
C13—C12—C19—C182.1 (4)C32—C31—C38—C371.6 (4)
N3—C12—C19—C18177.3 (2)N6—C31—C38—C37179.8 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg4 are the centroids of which rings?
D—H···AD—HH···AD···AD—H···A
C29—H29C···N3i0.982.493.334 (4)144
C17—H17A···Cg4i0.982.923.806 (3)151
C24—H24A···Cg1ii0.982.853.828 (3)175
C33—H33B···Cg4iii0.982.883.625 (3)134
Symmetry codes: (i) x, y1/2, z+3/2; (ii) x, y+1/2, z+3/2; (iii) x+1, y+1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
Cg1 and Cg4 are the centroids of which rings?
D—H···AD—HH···AD···AD—H···A
C29—H29C···N3i0.982.493.334 (4)144
C17—H17A···Cg4i0.982.923.806 (3)151
C24—H24A···Cg1ii0.982.853.828 (3)175
C33—H33B···Cg4iii0.982.883.625 (3)134
Symmetry codes: (i) x, y1/2, z+3/2; (ii) x, y+1/2, z+3/2; (iii) x+1, y+1/2, z+3/2.
 

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (grant No. 2012R1A1B3003337).

References

First citationBruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationDel Pino, J., Martinez, M. A., Castellano, V., Ramos, E., Martinez-Larranaga, M. R. & Anadon, A. (2013). Toxicology, 308, 88–95.  Web of Science CrossRef CAS PubMed
First citationHollingworth, R. M. (1976). Environ. Health Perspect. 14, 57–69.  CrossRef CAS PubMed
First citationPeoples, B. C., De la Vega, G., Valdebenito, C., Quijada, R., Ibañez, A., Valderrama, M. & Rojas, R. (2012). J. Organomet. Chem. 700, 147–153.  Web of Science CSD CrossRef CAS
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