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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 70| Part 12| December 2014| Pages o1266-o1267

Crystal structure of propaquizafop

aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
*Correspondence e-mail: jekim@gnu.ac.kr, thkim@gnu.ac.kr

Edited by P. C. Healy, Griffith University, Australia (Received 6 November 2014; accepted 11 November 2014; online 19 November 2014)

The title compound, C22H22ClN3O5 {systematic name: 2-(propan-2-yl­idene­amino­oxy)ethyl (R)-2-[4-(6-chloro­quin­oxalin-2-yl­oxy)phen­oxy]propionate}, is a herbicide. The asymmetric unit comprises two independent mol­ecules in which the dihedral angles between the phenyl ring and the quinoxaline ring plane are 75.93 (7) and 82.77 (8)°. The crystal structure features C—H⋯O, C—H⋯N, and C—H⋯Cl hydrogen bonds, as well as weak ππ inter­actions [ring-centroid separation = 3.782 (2) and 3.5952 (19) Å], resulting in a three-dimensional architecture.

1. Related literature

For information on the herbicidal properties of the title compound, see: Bergkvist & Ledin (1997[Bergkvist, P. & Ledin, S. (1997). Biomass Bioenergy, 12, 25-33.]). For a related crystal structure, see: Hu et al. (2009[Hu, J., Chen, G., Guo, L., Wang, J. & Xu, Y. (2009). Acta Cryst. E65, o2082.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C22H22ClN3O5

  • Mr = 443.88

  • Monoclinic, P 21

  • a = 4.6205 (2) Å

  • b = 21.9423 (10) Å

  • c = 21.1737 (10) Å

  • β = 93.263 (2)°

  • V = 2143.20 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.22 mm−1

  • T = 173 K

  • 0.47 × 0.05 × 0.04 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.905, Tmax = 0.991

  • 20815 measured reflections

  • 8319 independent reflections

  • 5996 reflections with I > 2σ(I)

  • Rint = 0.063

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.103

  • S = 0.99

  • 8319 reflections

  • 565 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.24 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 4004 Friedel pairs

  • Absolute structure parameter: 0.05 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4B⋯O2i 0.99 2.60 3.337 (4) 131
C7—H7⋯O3ii 1.00 2.33 3.264 (4) 154
C14—H14⋯O3ii 0.95 2.47 3.389 (4) 164
C22—H22⋯O8i 0.95 2.53 3.468 (4) 170
C27—H27A⋯O5ii 0.99 2.56 3.284 (4) 130
C29—H29⋯O8i 1.00 2.33 3.173 (4) 142
C44—H44⋯N1iii 0.95 2.51 3.430 (5) 162
C10—H10⋯Cl2iv 0.95 2.91 3.855 (4) 174
C25—H25A⋯Cl2v 0.98 2.99 3.368 (4) 105
C32—H32⋯Cl1vi 0.95 2.89 3.748 (4) 151
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) x+1, y, z-1; (iv) [-x-1, y-{\script{1\over 2}}, -z]; (v) x+1, y, z+1; (vi) [-x+2, y+{\script{1\over 2}}, -z].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2010[Brandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Propaquizafop, C22H22ClN3O5, is a herbicide of the aryloxy phenoxy propionate family. It is used for the post emergence control of a wide range of annual and perennial grasses. It is used for selective weed control in many broadleaf crops such as sugarbeet, oilseed rape, soybeans, sunflower, other field crops, vegetables, fruit trees, vineyards and forestry. (Bergkvist & Ledin, 1997). Its crystal structure is reported herein. 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 phenyl ring and quinoxaline ring planes are 75.93 (7) and 82.77 (8)°. All bond lengths and bond angles are normal and comparable to those observed in the crystal structure of a similar compound (Hu et al., 2009).

In the crystal structure (Fig. 2), The crystal structure is stabilized by C—H···O, C—H···N, and C—H···Cl hydrogen bonds (Table 1), as well as two weak intermolecular ππ interactions between the quinoxaline rings [Cg1···Cg2i = 3.782 (2) Å. Cg1 and Cg2 are the centroids of the C15—N2—C16—C21—N3—C22 and the C16—C21 rings, respectively. Cg3···Cg4ii = 3.5952 (19) Å. Cg3 and Cg4 are the centroid of the C37—N5—C38—C43—N6—C44 and the C38—C43 rings, respectively. (Symmetry codes: (i), x - 1, y, z and (ii), x + 1, y, z)], resulting in a three-dimensional architecture.

Related literature top

For information on the herbicidal properties of the title compound, see: Bergkvist & Ledin (1997). For a related crystal structure, see: Hu et al. (2009).

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH3OH gave single crystals suitable for X-ray analysis.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.98 Å, Uiso = 1.5Ueq(C) for methyl group, d(C—H) = 0.99 Å, Uiso = 1.2Ueq(C) for Csp3—H, d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic C—H, and d(C—H) = 1.00 Å, Uiso = 1.5Ueq(C) for Csp3—H.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
Fig. 1. The asymmetric unit of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.

Fig. 2. Crystal packing viewed along the a axis. The intermolecular C—H···N, C—H···O, and C—H···Cl hydrogen bonds are shown as dashed lines.
2-(Propan-2-ylideneaminooxy)ethyl (R)-2-[4-(6-chloroquinoxalin-2-yloxy)phenoxy]propionate top
Crystal data top
C22H22ClN3O5F(000) = 928
Mr = 443.88Dx = 1.376 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2323 reflections
a = 4.6205 (2) Åθ = 2.7–19.3°
b = 21.9423 (10) ŵ = 0.22 mm1
c = 21.1737 (10) ÅT = 173 K
β = 93.263 (2)°Needle, colourless
V = 2143.20 (17) Å30.47 × 0.05 × 0.04 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer
8319 independent reflections
Radiation source: fine-focus sealed tube5996 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ϕ and ω scansθmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 55
Tmin = 0.905, Tmax = 0.991k = 2627
20815 measured reflectionsl = 2626
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0354P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
8319 reflectionsΔρmax = 0.26 e Å3
565 parametersΔρmin = 0.24 e Å3
1 restraintAbsolute structure: Flack (1983), 4004 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (6)
Crystal data top
C22H22ClN3O5V = 2143.20 (17) Å3
Mr = 443.88Z = 4
Monoclinic, P21Mo Kα radiation
a = 4.6205 (2) ŵ = 0.22 mm1
b = 21.9423 (10) ÅT = 173 K
c = 21.1737 (10) Å0.47 × 0.05 × 0.04 mm
β = 93.263 (2)°
Data collection top
Bruker APEXII CCD
diffractometer
8319 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
5996 reflections with I > 2σ(I)
Tmin = 0.905, Tmax = 0.991Rint = 0.063
20815 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.103Δρmax = 0.26 e Å3
S = 0.99Δρmin = 0.24 e Å3
8319 reflectionsAbsolute structure: Flack (1983), 4004 Friedel pairs
565 parametersAbsolute structure parameter: 0.05 (6)
1 restraint
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
Cl10.8646 (2)0.58056 (5)0.01482 (4)0.0403 (3)
Cl20.2992 (2)0.91749 (4)0.39805 (4)0.0328 (2)
O10.0906 (5)0.62880 (10)0.75631 (10)0.0300 (6)
O20.1079 (5)0.64050 (10)0.62762 (10)0.0263 (6)
O30.2656 (5)0.63233 (11)0.55516 (10)0.0296 (6)
O40.0116 (6)0.53477 (11)0.49904 (10)0.0282 (6)
O50.0140 (6)0.67388 (11)0.28083 (10)0.0305 (6)
O60.6212 (6)0.84357 (11)0.39165 (11)0.0323 (6)
O70.3833 (5)0.83763 (10)0.25968 (10)0.0254 (6)
O80.7468 (5)0.84570 (11)0.19415 (10)0.0291 (6)
O90.4940 (5)0.94441 (10)0.13532 (10)0.0281 (6)
O100.6648 (5)0.82773 (10)0.09140 (10)0.0315 (6)
N10.0042 (7)0.67417 (13)0.80229 (13)0.0281 (7)
N20.2541 (6)0.60906 (13)0.22060 (12)0.0235 (7)
N30.2624 (7)0.70563 (13)0.13081 (13)0.0286 (7)
N40.5470 (7)0.79627 (13)0.43496 (13)0.0328 (8)
N50.3225 (6)0.88493 (13)0.14960 (12)0.0241 (7)
N60.4407 (7)0.80739 (13)0.25283 (14)0.0264 (7)
C10.2912 (9)0.58894 (17)0.84480 (18)0.0407 (10)
H1A0.13130.55970.84630.061*
H1B0.42440.58340.88210.061*
H1C0.39540.58210.80640.061*
C20.1739 (8)0.65195 (16)0.84430 (16)0.0260 (8)
C30.2718 (9)0.69528 (17)0.89626 (16)0.0369 (10)
H3A0.17480.73460.88940.055*
H3B0.48210.70090.89600.055*
H3C0.22220.67850.93720.055*
C40.2490 (8)0.65898 (18)0.70522 (16)0.0330 (9)
H4A0.37310.69100.72260.040*
H4B0.37700.62920.68230.040*
C50.0510 (8)0.68746 (16)0.65971 (16)0.0288 (9)
H5A0.16640.71200.62810.035*
H5B0.08730.71500.68290.035*
C60.0370 (8)0.61396 (16)0.57733 (15)0.0231 (8)
C70.1219 (8)0.55835 (15)0.55631 (15)0.0239 (8)
H70.32960.56840.55040.029*
C80.1005 (10)0.50749 (17)0.60594 (16)0.0375 (10)
H8A0.10380.49940.61290.056*
H8B0.20050.52030.64580.056*
H8C0.19120.47030.59070.056*
C90.0115 (8)0.56995 (15)0.44475 (15)0.0220 (8)
C100.1660 (8)0.55205 (16)0.39339 (16)0.0293 (9)
H100.28710.51730.39640.035*
C110.1670 (8)0.58495 (17)0.33742 (16)0.0291 (9)
H110.28950.57320.30190.035*
C120.0091 (8)0.63397 (16)0.33417 (15)0.0253 (9)
C130.1930 (8)0.65152 (18)0.38381 (16)0.0332 (9)
H130.31660.68580.37990.040*
C140.1968 (8)0.61839 (16)0.44033 (16)0.0278 (9)
H140.32570.62930.47510.033*
C150.1284 (8)0.66053 (16)0.22798 (15)0.0234 (8)
C160.3954 (7)0.60351 (15)0.16469 (15)0.0219 (8)
C170.5290 (8)0.54843 (15)0.15090 (16)0.0252 (8)
H170.52280.51550.18000.030*
C180.6692 (8)0.54103 (17)0.09599 (16)0.0289 (9)
H180.75720.50320.08660.035*
C190.6801 (8)0.59032 (17)0.05409 (15)0.0279 (9)
C200.5540 (8)0.64459 (17)0.06578 (16)0.0282 (9)
H200.56780.67750.03690.034*
C210.4019 (7)0.65187 (16)0.12123 (15)0.0213 (8)
C220.1234 (8)0.70974 (17)0.18315 (15)0.0289 (9)
H220.01810.74580.19150.035*
C230.2920 (10)0.77216 (18)0.52389 (18)0.0457 (12)
H23A0.38710.73310.51640.069*
H23B0.08120.76660.52070.069*
H23C0.35220.78710.56620.069*
C240.3764 (8)0.81741 (17)0.47554 (17)0.0305 (9)
C250.2581 (9)0.88020 (18)0.47602 (18)0.0398 (10)
H25A0.41600.90950.47210.060*
H25B0.16520.88730.51580.060*
H25C0.11490.88530.44050.060*
C260.7593 (8)0.81513 (19)0.34125 (16)0.0341 (10)
H26A0.88590.78190.35830.041*
H26B0.88280.84530.32070.041*
C270.5417 (8)0.78956 (17)0.29305 (16)0.0278 (9)
H27A0.64280.76430.26240.033*
H27B0.40420.76300.31440.033*
C280.5173 (7)0.86318 (16)0.21119 (15)0.0212 (8)
C290.3410 (7)0.91649 (16)0.18402 (14)0.0255 (8)
H290.14710.90200.16680.031*
C300.3044 (9)0.96437 (17)0.23452 (17)0.0403 (10)
H30A0.49550.97870.25060.060*
H30B0.20150.94660.26930.060*
H30C0.19260.99870.21630.060*
C310.5158 (8)0.91335 (16)0.07887 (15)0.0246 (8)
C320.6921 (9)0.93993 (17)0.03696 (16)0.0409 (11)
H320.78510.97740.04770.049*
C330.7369 (9)0.91307 (18)0.02070 (16)0.0377 (10)
H330.86070.93160.04950.045*
C340.6009 (8)0.85980 (16)0.03539 (15)0.0268 (9)
C350.4212 (9)0.83233 (18)0.00528 (17)0.0390 (10)
H350.32670.79520.00620.047*
C360.3778 (9)0.85927 (18)0.06367 (17)0.0386 (10)
H360.25500.84060.09250.046*
C370.5101 (8)0.84137 (16)0.14593 (15)0.0243 (8)
C380.1798 (7)0.89193 (15)0.20807 (15)0.0200 (8)
C390.0240 (8)0.93925 (15)0.21804 (15)0.0261 (9)
H390.06340.96560.18400.031*
C400.1663 (8)0.94788 (16)0.27590 (16)0.0279 (9)
H400.29950.98060.28250.034*
C410.1115 (7)0.90744 (16)0.32525 (14)0.0240 (8)
C420.0835 (8)0.86119 (15)0.31783 (15)0.0238 (8)
H420.11560.83440.35200.029*
C430.2374 (7)0.85328 (14)0.25905 (15)0.0201 (8)
C440.5739 (8)0.80277 (16)0.19749 (16)0.0259 (9)
H440.71950.77250.19100.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0453 (6)0.0483 (6)0.0288 (5)0.0108 (5)0.0144 (5)0.0064 (5)
Cl20.0361 (5)0.0393 (6)0.0225 (5)0.0037 (5)0.0025 (4)0.0023 (4)
O10.0389 (16)0.0270 (14)0.0235 (13)0.0008 (12)0.0035 (12)0.0057 (11)
O20.0294 (14)0.0267 (14)0.0223 (13)0.0021 (12)0.0034 (11)0.0083 (11)
O30.0254 (15)0.0379 (16)0.0249 (13)0.0003 (13)0.0017 (12)0.0050 (12)
O40.0424 (16)0.0261 (14)0.0157 (12)0.0112 (12)0.0006 (11)0.0004 (11)
O50.0466 (17)0.0275 (14)0.0178 (13)0.0077 (12)0.0063 (12)0.0043 (11)
O60.0375 (16)0.0358 (15)0.0241 (13)0.0003 (13)0.0052 (12)0.0088 (12)
O70.0231 (13)0.0284 (14)0.0250 (13)0.0026 (12)0.0038 (11)0.0060 (11)
O80.0222 (14)0.0377 (15)0.0276 (14)0.0018 (12)0.0035 (12)0.0045 (12)
O90.0397 (16)0.0276 (14)0.0170 (12)0.0090 (12)0.0032 (11)0.0008 (11)
O100.0419 (16)0.0302 (15)0.0216 (13)0.0092 (13)0.0050 (12)0.0034 (12)
N10.0331 (19)0.0289 (17)0.0220 (16)0.0028 (15)0.0009 (14)0.0100 (14)
N20.0311 (18)0.0234 (16)0.0158 (15)0.0000 (14)0.0011 (13)0.0029 (13)
N30.0353 (19)0.0267 (17)0.0235 (17)0.0002 (15)0.0017 (15)0.0017 (14)
N40.043 (2)0.0327 (19)0.0233 (16)0.0008 (16)0.0065 (15)0.0046 (14)
N50.0247 (17)0.0284 (17)0.0193 (16)0.0030 (14)0.0013 (13)0.0013 (13)
N60.0309 (18)0.0244 (17)0.0243 (16)0.0005 (14)0.0055 (14)0.0015 (13)
C10.053 (3)0.030 (2)0.038 (2)0.012 (2)0.011 (2)0.0010 (19)
C20.028 (2)0.026 (2)0.0237 (19)0.0005 (18)0.0001 (17)0.0068 (17)
C30.048 (3)0.034 (2)0.027 (2)0.013 (2)0.0103 (19)0.0029 (18)
C40.034 (2)0.040 (2)0.024 (2)0.0076 (19)0.0062 (18)0.0059 (18)
C50.035 (2)0.027 (2)0.024 (2)0.0032 (18)0.0065 (18)0.0080 (17)
C60.029 (2)0.025 (2)0.0155 (18)0.0086 (17)0.0015 (17)0.0016 (15)
C70.032 (2)0.022 (2)0.0173 (18)0.0014 (17)0.0016 (16)0.0011 (15)
C80.059 (3)0.033 (2)0.020 (2)0.002 (2)0.0043 (19)0.0050 (17)
C90.032 (2)0.0193 (19)0.0152 (17)0.0006 (17)0.0040 (16)0.0033 (15)
C100.042 (3)0.022 (2)0.023 (2)0.0073 (18)0.0009 (18)0.0033 (16)
C110.038 (2)0.030 (2)0.0189 (19)0.0020 (19)0.0052 (17)0.0034 (17)
C120.037 (2)0.024 (2)0.0153 (18)0.0048 (18)0.0052 (17)0.0036 (16)
C130.038 (2)0.034 (2)0.028 (2)0.008 (2)0.0040 (18)0.0044 (18)
C140.034 (2)0.030 (2)0.0196 (19)0.0085 (18)0.0007 (17)0.0008 (16)
C150.029 (2)0.027 (2)0.0139 (18)0.0001 (17)0.0020 (16)0.0030 (16)
C160.0194 (19)0.027 (2)0.0194 (18)0.0013 (16)0.0000 (15)0.0009 (16)
C170.026 (2)0.025 (2)0.0254 (19)0.0038 (17)0.0040 (17)0.0040 (16)
C180.027 (2)0.029 (2)0.030 (2)0.0049 (18)0.0011 (17)0.0008 (18)
C190.026 (2)0.036 (2)0.0222 (19)0.0042 (18)0.0059 (16)0.0016 (18)
C200.031 (2)0.034 (2)0.0192 (19)0.0055 (19)0.0001 (16)0.0060 (17)
C210.0196 (19)0.0236 (19)0.0201 (18)0.0028 (16)0.0040 (15)0.0018 (16)
C220.039 (2)0.029 (2)0.0194 (19)0.0053 (18)0.0025 (18)0.0009 (17)
C230.068 (3)0.037 (2)0.033 (2)0.003 (2)0.016 (2)0.003 (2)
C240.031 (2)0.036 (2)0.024 (2)0.0034 (19)0.0017 (18)0.0006 (18)
C250.040 (3)0.045 (3)0.033 (2)0.008 (2)0.0057 (19)0.002 (2)
C260.028 (2)0.054 (3)0.0202 (19)0.005 (2)0.0053 (18)0.0095 (19)
C270.031 (2)0.031 (2)0.0220 (19)0.0077 (18)0.0042 (17)0.0046 (17)
C280.017 (2)0.030 (2)0.0165 (18)0.0079 (17)0.0005 (16)0.0017 (16)
C290.027 (2)0.029 (2)0.0208 (18)0.0007 (18)0.0049 (15)0.0035 (17)
C300.057 (3)0.031 (2)0.034 (2)0.009 (2)0.017 (2)0.0004 (19)
C310.031 (2)0.0233 (19)0.0184 (18)0.0026 (18)0.0036 (16)0.0040 (17)
C320.064 (3)0.030 (2)0.029 (2)0.021 (2)0.014 (2)0.0051 (19)
C330.058 (3)0.028 (2)0.029 (2)0.010 (2)0.015 (2)0.0014 (19)
C340.034 (2)0.028 (2)0.0175 (19)0.0055 (18)0.0023 (17)0.0023 (16)
C350.053 (3)0.035 (2)0.028 (2)0.018 (2)0.002 (2)0.0017 (19)
C360.047 (3)0.044 (3)0.024 (2)0.018 (2)0.0026 (19)0.0025 (19)
C370.029 (2)0.023 (2)0.0212 (19)0.0014 (18)0.0015 (16)0.0007 (16)
C380.026 (2)0.0174 (17)0.0166 (18)0.0062 (16)0.0021 (15)0.0030 (15)
C390.030 (2)0.026 (2)0.0219 (19)0.0020 (17)0.0033 (17)0.0062 (16)
C400.027 (2)0.028 (2)0.029 (2)0.0051 (17)0.0014 (17)0.0040 (17)
C410.0268 (19)0.030 (2)0.0154 (17)0.0042 (18)0.0004 (15)0.0016 (16)
C420.028 (2)0.0245 (19)0.0199 (19)0.0019 (17)0.0064 (16)0.0062 (16)
C430.024 (2)0.0132 (17)0.0236 (19)0.0045 (15)0.0032 (16)0.0005 (15)
C440.029 (2)0.022 (2)0.027 (2)0.0024 (17)0.0046 (18)0.0017 (16)
Geometric parameters (Å, º) top
Cl1—C191.745 (3)C12—C131.369 (5)
Cl2—C411.739 (3)C13—C141.399 (5)
O1—C41.433 (4)C13—H130.9500
O1—N11.433 (3)C14—H140.9500
O2—C61.357 (4)C15—C221.437 (5)
O2—C51.456 (4)C16—C171.396 (4)
O3—C61.201 (4)C16—C211.406 (4)
O4—C91.394 (4)C17—C181.372 (5)
O4—C71.426 (4)C17—H170.9500
O5—C151.362 (4)C18—C191.402 (5)
O5—C121.428 (4)C18—H180.9500
O6—C261.419 (4)C19—C201.355 (5)
O6—N41.439 (3)C20—C211.411 (5)
O7—C281.351 (4)C20—H200.9500
O7—C271.445 (4)C22—H220.9500
O8—C281.202 (4)C23—C241.494 (5)
O9—C311.384 (4)C23—H23A0.9800
O9—C291.422 (4)C23—H23B0.9800
O10—C371.356 (4)C23—H23C0.9800
O10—C341.424 (4)C24—C251.482 (5)
N1—C21.274 (4)C25—H25A0.9800
N2—C151.283 (4)C25—H25B0.9800
N2—C161.390 (4)C25—H25C0.9800
N3—C221.315 (4)C26—C271.500 (5)
N3—C211.365 (4)C26—H26A0.9900
N4—C241.285 (4)C26—H26B0.9900
N5—C371.290 (4)C27—H27A0.9900
N5—C381.378 (4)C27—H27B0.9900
N6—C441.296 (4)C28—C291.520 (5)
N6—C431.378 (4)C29—C301.515 (5)
C1—C21.485 (5)C29—H291.0000
C1—H1A0.9800C30—H30A0.9800
C1—H1B0.9800C30—H30B0.9800
C1—H1C0.9800C30—H30C0.9800
C2—C31.504 (5)C31—C321.369 (5)
C3—H3A0.9800C31—C361.376 (5)
C3—H3B0.9800C32—C331.382 (5)
C3—H3C0.9800C32—H320.9500
C4—C51.502 (5)C33—C341.355 (5)
C4—H4A0.9900C33—H330.9500
C4—H4B0.9900C34—C351.370 (5)
C5—H5A0.9900C35—C361.395 (5)
C5—H5B0.9900C35—H350.9500
C6—C71.504 (5)C36—H360.9500
C7—C81.540 (4)C37—C441.426 (5)
C7—H71.0000C38—C391.410 (5)
C8—H8A0.9800C38—C431.410 (4)
C8—H8B0.9800C39—C401.370 (5)
C8—H8C0.9800C39—H390.9500
C9—C141.371 (5)C40—C411.405 (5)
C9—C101.381 (5)C40—H400.9500
C10—C111.387 (5)C41—C421.360 (5)
C10—H100.9500C42—C431.409 (5)
C11—C121.353 (5)C42—H420.9500
C11—H110.9500C44—H440.9500
C4—O1—N1107.6 (3)C21—C20—H20120.3
C6—O2—C5115.5 (3)N3—C21—C16121.8 (3)
C9—O4—C7116.8 (2)N3—C21—C20118.9 (3)
C15—O5—C12120.0 (3)C16—C21—C20119.3 (3)
C26—O6—N4107.2 (3)N3—C22—C15121.0 (3)
C28—O7—C27115.7 (3)N3—C22—H22119.5
C31—O9—C29118.5 (3)C15—C22—H22119.5
C37—O10—C34118.4 (3)C24—C23—H23A109.5
C2—N1—O1110.6 (3)C24—C23—H23B109.5
C15—N2—C16114.7 (3)H23A—C23—H23B109.5
C22—N3—C21116.2 (3)C24—C23—H23C109.5
C24—N4—O6110.1 (3)H23A—C23—H23C109.5
C37—N5—C38115.0 (3)H23B—C23—H23C109.5
C44—N6—C43115.4 (3)N4—C24—C25125.5 (3)
C2—C1—H1A109.5N4—C24—C23114.3 (3)
C2—C1—H1B109.5C25—C24—C23120.1 (3)
H1A—C1—H1B109.5C24—C25—H25A109.5
C2—C1—H1C109.5C24—C25—H25B109.5
H1A—C1—H1C109.5H25A—C25—H25B109.5
H1B—C1—H1C109.5C24—C25—H25C109.5
N1—C2—C1125.6 (3)H25A—C25—H25C109.5
N1—C2—C3115.1 (3)H25B—C25—H25C109.5
C1—C2—C3119.3 (3)O6—C26—C27111.3 (3)
C2—C3—H3A109.5O6—C26—H26A109.4
C2—C3—H3B109.5C27—C26—H26A109.4
H3A—C3—H3B109.5O6—C26—H26B109.4
C2—C3—H3C109.5C27—C26—H26B109.4
H3A—C3—H3C109.5H26A—C26—H26B108.0
H3B—C3—H3C109.5O7—C27—C26111.2 (3)
O1—C4—C5111.9 (3)O7—C27—H27A109.4
O1—C4—H4A109.2C26—C27—H27A109.4
C5—C4—H4A109.2O7—C27—H27B109.4
O1—C4—H4B109.2C26—C27—H27B109.4
C5—C4—H4B109.2H27A—C27—H27B108.0
H4A—C4—H4B107.9O8—C28—O7123.1 (3)
O2—C5—C4110.3 (3)O8—C28—C29126.5 (3)
O2—C5—H5A109.6O7—C28—C29110.4 (3)
C4—C5—H5A109.6O9—C29—C30107.1 (3)
O2—C5—H5B109.6O9—C29—C28109.2 (3)
C4—C5—H5B109.6C30—C29—C28110.2 (3)
H5A—C5—H5B108.1O9—C29—H29110.1
O3—C6—O2123.1 (3)C30—C29—H29110.1
O3—C6—C7126.2 (3)C28—C29—H29110.1
O2—C6—C7110.7 (3)C29—C30—H30A109.5
O4—C7—C6110.6 (3)C29—C30—H30B109.5
O4—C7—C8106.0 (3)H30A—C30—H30B109.5
C6—C7—C8109.6 (3)C29—C30—H30C109.5
O4—C7—H7110.2H30A—C30—H30C109.5
C6—C7—H7110.2H30B—C30—H30C109.5
C8—C7—H7110.2C32—C31—C36120.0 (3)
C7—C8—H8A109.5C32—C31—O9115.2 (3)
C7—C8—H8B109.5C36—C31—O9124.8 (3)
H8A—C8—H8B109.5C31—C32—C33121.0 (4)
C7—C8—H8C109.5C31—C32—H32119.5
H8A—C8—H8C109.5C33—C32—H32119.5
H8B—C8—H8C109.5C34—C33—C32118.7 (3)
C14—C9—C10120.8 (3)C34—C33—H33120.7
C14—C9—O4124.3 (3)C32—C33—H33120.7
C10—C9—O4115.0 (3)C33—C34—C35121.7 (3)
C9—C10—C11119.8 (3)C33—C34—O10120.1 (3)
C9—C10—H10120.1C35—C34—O10117.9 (3)
C11—C10—H10120.1C34—C35—C36119.6 (4)
C12—C11—C10119.0 (3)C34—C35—H35120.2
C12—C11—H11120.5C36—C35—H35120.2
C10—C11—H11120.5C31—C36—C35119.0 (4)
C11—C12—C13122.3 (3)C31—C36—H36120.5
C11—C12—O5120.6 (3)C35—C36—H36120.5
C13—C12—O5116.7 (3)N5—C37—O10122.3 (3)
C12—C13—C14119.2 (3)N5—C37—C44124.2 (3)
C12—C13—H13120.4O10—C37—C44113.5 (3)
C14—C13—H13120.4N5—C38—C39119.9 (3)
C9—C14—C13118.9 (3)N5—C38—C43121.3 (3)
C9—C14—H14120.5C39—C38—C43118.8 (3)
C13—C14—H14120.5C40—C39—C38121.2 (3)
N2—C15—O5122.2 (3)C40—C39—H39119.4
N2—C15—C22124.8 (3)C38—C39—H39119.4
O5—C15—C22113.0 (3)C39—C40—C41118.7 (3)
N2—C16—C17119.3 (3)C39—C40—H40120.7
N2—C16—C21121.3 (3)C41—C40—H40120.7
C17—C16—C21119.4 (3)C42—C41—C40122.1 (3)
C18—C17—C16121.0 (3)C42—C41—Cl2119.4 (3)
C18—C17—H17119.5C40—C41—Cl2118.5 (3)
C16—C17—H17119.5C41—C42—C43119.5 (3)
C17—C18—C19118.7 (3)C41—C42—H42120.3
C17—C18—H18120.6C43—C42—H42120.3
C19—C18—H18120.6N6—C43—C42118.8 (3)
C20—C19—C18122.1 (3)N6—C43—C38121.6 (3)
C20—C19—Cl1119.8 (3)C42—C43—C38119.6 (3)
C18—C19—Cl1118.1 (3)N6—C44—C37122.5 (3)
C19—C20—C21119.4 (3)N6—C44—H44118.7
C19—C20—H20120.3C37—C44—H44118.7
C4—O1—N1—C2170.3 (3)O5—C15—C22—N3176.7 (3)
C26—O6—N4—C24168.5 (3)O6—N4—C24—C253.3 (5)
O1—N1—C2—C13.1 (5)O6—N4—C24—C23178.5 (3)
O1—N1—C2—C3178.1 (3)N4—O6—C26—C2782.3 (3)
N1—O1—C4—C582.1 (3)C28—O7—C27—C2682.3 (3)
C6—O2—C5—C482.2 (3)O6—C26—C27—O768.3 (4)
O1—C4—C5—O266.0 (4)C27—O7—C28—O83.6 (4)
C5—O2—C6—O39.0 (4)C27—O7—C28—C29175.0 (3)
C5—O2—C6—C7168.6 (3)C31—O9—C29—C30169.9 (3)
C9—O4—C7—C668.8 (4)C31—O9—C29—C2870.8 (4)
C9—O4—C7—C8172.5 (3)O8—C28—C29—O91.5 (5)
O3—C6—C7—O49.4 (5)O7—C28—C29—O9177.0 (2)
O2—C6—C7—O4173.0 (3)O8—C28—C29—C30118.8 (4)
O3—C6—C7—C8107.1 (4)O7—C28—C29—C3059.7 (4)
O2—C6—C7—C870.5 (4)C29—O9—C31—C32173.2 (3)
C7—O4—C9—C1413.2 (5)C29—O9—C31—C366.1 (5)
C7—O4—C9—C10167.8 (3)C36—C31—C32—C330.5 (6)
C14—C9—C10—C112.9 (5)O9—C31—C32—C33178.8 (3)
O4—C9—C10—C11178.1 (3)C31—C32—C33—C340.5 (6)
C9—C10—C11—C120.5 (5)C32—C33—C34—C350.1 (6)
C10—C11—C12—C131.4 (6)C32—C33—C34—O10173.6 (3)
C10—C11—C12—O5171.3 (3)C37—O10—C34—C3388.6 (4)
C15—O5—C12—C1185.1 (4)C37—O10—C34—C3597.5 (4)
C15—O5—C12—C13101.8 (4)C33—C34—C35—C360.6 (6)
C11—C12—C13—C141.0 (6)O10—C34—C35—C36173.3 (3)
O5—C12—C13—C14172.0 (3)C32—C31—C36—C350.1 (6)
C10—C9—C14—C133.2 (5)O9—C31—C36—C35179.2 (3)
O4—C9—C14—C13177.8 (3)C34—C35—C36—C310.5 (6)
C12—C13—C14—C91.3 (6)C38—N5—C37—O10178.7 (3)
C16—N2—C15—O5178.5 (3)C38—N5—C37—C440.6 (5)
C16—N2—C15—C220.9 (5)C34—O10—C37—N54.8 (5)
C12—O5—C15—N29.3 (5)C34—O10—C37—C44174.6 (3)
C12—O5—C15—C22170.1 (3)C37—N5—C38—C39178.2 (3)
C15—N2—C16—C17177.4 (3)C37—N5—C38—C430.6 (5)
C15—N2—C16—C211.4 (5)N5—C38—C39—C40179.1 (3)
N2—C16—C17—C18179.6 (3)C43—C38—C39—C400.3 (5)
C21—C16—C17—C180.8 (5)C38—C39—C40—C411.7 (5)
C16—C17—C18—C191.0 (5)C39—C40—C41—C421.8 (5)
C17—C18—C19—C200.8 (6)C39—C40—C41—Cl2178.5 (3)
C17—C18—C19—Cl1178.9 (3)C40—C41—C42—C430.2 (5)
C18—C19—C20—C211.2 (5)Cl2—C41—C42—C43179.5 (3)
Cl1—C19—C20—C21179.2 (3)C44—N6—C43—C42180.0 (3)
C22—N3—C21—C160.5 (5)C44—N6—C43—C380.3 (5)
C22—N3—C21—C20179.7 (3)C41—C42—C43—N6178.0 (3)
N2—C16—C21—N32.2 (5)C41—C42—C43—C382.3 (5)
C17—C16—C21—N3176.6 (3)N5—C38—C43—N60.8 (5)
N2—C16—C21—C20178.5 (3)C39—C38—C43—N6178.0 (3)
C17—C16—C21—C202.7 (5)N5—C38—C43—C42178.9 (3)
C19—C20—C21—N3176.5 (3)C39—C38—C43—C422.4 (5)
C19—C20—C21—C162.9 (5)C43—N6—C44—C371.5 (5)
C21—N3—C22—C151.8 (5)N5—C37—C44—N61.8 (6)
N2—C15—C22—N32.7 (6)O10—C37—C44—N6177.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O2i0.992.603.337 (4)131
C7—H7···O3ii1.002.333.264 (4)154
C14—H14···O3ii0.952.473.389 (4)164
C22—H22···O8i0.952.533.468 (4)170
C27—H27A···O5ii0.992.563.284 (4)130
C29—H29···O8i1.002.333.173 (4)142
C44—H44···N1iii0.952.513.430 (5)162
C10—H10···Cl2iv0.952.913.855 (4)174
C25—H25A···Cl2v0.982.993.368 (4)105
C32—H32···Cl1vi0.952.893.748 (4)151
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x+1, y, z1; (iv) x1, y1/2, z; (v) x+1, y, z+1; (vi) x+2, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4B···O2i0.992.603.337 (4)131.4
C7—H7···O3ii1.002.333.264 (4)154.1
C14—H14···O3ii0.952.473.389 (4)163.9
C22—H22···O8i0.952.533.468 (4)170.4
C27—H27A···O5ii0.992.563.284 (4)130.2
C29—H29···O8i1.002.333.173 (4)141.9
C44—H44···N1iii0.952.513.430 (5)161.7
C10—H10···Cl2iv0.952.913.855 (4)174.4
C25—H25A···Cl2v0.982.993.368 (4)104.6
C32—H32···Cl1vi0.952.893.748 (4)150.8
Symmetry codes: (i) x1, y, z; (ii) x+1, y, z; (iii) x+1, y, z1; (iv) x1, y1/2, z; (v) x+1, y, z+1; (vi) x+2, y+1/2, z.
 

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 (No. 2012R1A1B3003337).

References

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First citationBrandenburg, K. (2010). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationHu, J., Chen, G., Guo, L., Wang, J. & Xu, Y. (2009). Acta Cryst. E65, o2082.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 12| December 2014| Pages o1266-o1267
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