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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2630.
Published online 2009 October 3. doi:  10.1107/S1600536809038677
PMCID: PMC2971071

(RS)-Dimethyl­ammonium 2-sec-butyl-4,6-dinitro­phenolate

Abstract

The title compound, C2H8N+·C10H11N2O5 , is a highly toxic herbicide known as dinoseb. The sec-butyl group is disordered [occupancy ratio 0.828 (3):0.172 (3)], while the nitro group in the 6 position is twisted by 25° with respect to the ring plane. Pairs of –O(...)H—N+—H(...)O– bridges between phenolic O atoms generate eight-membered hydrogen-bonded rings.

Related literature

For toxicicity information, see: EXTOXNET (1996 [triangle]). Related structures have been described by Smith et al. (2002 [triangle], 2005 [triangle]); Lynch & McClenaghan (2004 [triangle]); West-Nielsen et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2630-scheme1.jpg

Experimental

Crystal data

  • C2H8N+·C10H11N2O5
  • M r = 285.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2630-efi1.jpg
  • a = 16.804 (4) Å
  • b = 9.1446 (17) Å
  • c = 19.223 (4) Å
  • β = 104.555 (6)°
  • V = 2859.2 (10) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 105 K
  • 0.70 × 0.09 × 0.05 mm

Data collection

  • Siemens SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.832, T max = 0.995
  • 10444 measured reflections
  • 2909 independent reflections
  • 2382 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.094
  • S = 1.05
  • 2909 reflections
  • 219 parameters
  • 45 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus ; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038677/pk2194sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038677/pk2194Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Large amounts of a highly volatile yellow powder of unknown origin was discovered below the floor planks in the attic of a private home, and a small quantity was forwarded to the University of Oslo for analysis. Single crystals were easily obtained, and subsequent structure determination by X-ray diffraction identified the sample as a dimethylammonium salt of 2-sec-butyl-4,6-dinitrophenol, with common name dinoseb (I). This herbicide has been used in soybeans, vegetables, fruits and nuts, citrus, and other field crops for the selective control of grass and broadleaf weeds (e.g., in corn). It was also used as an insecticide in grapes and as a seed crop drying agent. Product names for pesticides containing dinoseb include Basanite, Caldon, Chemox, Chemsect DNBP, Dinitro, Dynamyte, Elgetol, Gebutox, Hel-Fire, Kiloseb, Nitropone, Premerge, Sinox General, Subitex, and Vertac Weed Killer. The use of dinoseb was prohibited in the U.S. in 1986, an action based on the potential risk of birth defects and other adverse health effects (EXTOXNET, 1996).

2-sec-butyl-4,6-dinitrophenol has a chiral C-atom at C7, and the title salt is racemic, space group C2/c. For simplicity, the R-form alone is shown in Fig. 1, but there is actually disorder at each phenolate position giving a 0.828 (3):0.172 (3) distribution between the R-form and the S-form, as in Fig. 2, or vice versa. Both ammonium H-atoms form strong hydrogen bonds to charged phenolate O atom acceptors, one interaction is visible in Fig. 1.

Related structures include achiral analogues with tert-butyl (Lynch & McClenaghan, 2004) and acetyl (= 2-hydroxy-3,5-dinitroacetophenone; West-Nielsen et al., 2006) substituents rather than sec-butyl at C2 (both obtained as neutral molecules) as well as a series of proton-transfer complexes of 3,5-dinitrosalicylic acid with aliphatic amines (Smith et al., 2002; Smith et al., 2005).

Experimental

Crystals in the shape of fine, yellow needles were grown by slow evaporation of a diethylether solution of the title complex.

Refinement

Normal anisotropic refinement except for atoms with low occupancy (minor disorder component), which were either refined isotropically (sec-butyl group) or constrained to have the same thermal parameters as the near-by atom of the major disorder component (C1, C2, C3). The geometries of the minor and the major component, in terms of covalent bond lengths and bond angles, were restrained to be more or less similar by a SHELXTL SAME command. Positional parameters were refined for the two ammonium H atoms involved in hydrogen bonding, other H atoms were positioned with idealized geometry and C–H distances fixed in the range 0.95 to 0.99 Å. Uiso values were 1.2Ueq of the carrier atom, or 1.5Ueq for the methyl groups.

Figures

Fig. 1.
: The molecular structure of (I) (major disorder component). Displacement ellipsoids are shown at the 50% probability level and H-atoms are shown as spheres of arbitrary size.
Fig. 2.
: Disorder for the sec-butyl group and neighbouring atoms. Normal, light colour is used for the major component with R-configuration at C7, the minor component with S-configuration appears in darker colour.

Crystal data

C2H8N+·C10H11N2O5F(000) = 1216
Mr = 285.30Dx = 1.326 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 16.804 (4) ÅCell parameters from 4501 reflections
b = 9.1446 (17) Åθ = 2.2–26.4°
c = 19.223 (4) ŵ = 0.10 mm1
β = 104.555 (6)°T = 105 K
V = 2859.2 (10) Å3Needle, yellow
Z = 80.70 × 0.09 × 0.05 mm

Data collection

Siemens SMART CCD diffractometer2909 independent reflections
Radiation source: fine-focus sealed tube2382 reflections with I > 2σ(I)
graphiteRint = 0.026
Detector resolution: 8.3 pixels mm-1θmax = 26.4°, θmin = 2.2°
ω scansh = −20→20
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −11→11
Tmin = 0.832, Tmax = 0.995l = −23→22
10444 measured reflections

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H atoms treated by a mixture of independent and constrained refinement
S = 1.05w = 1/[σ2(Fo2) + (0.0469P)2 + 1.2758P] where P = (Fo2 + 2Fc2)/3
2909 reflections(Δ/σ)max = 0.002
219 parametersΔρmax = 0.21 e Å3
45 restraintsΔρmin = −0.20 e Å3

Special details

Experimental. Crystallized from diethyl ether.Three sets of frames each taken over 0.3° ω rotation with 20 s exposure time. Detector set at 2θ = 27°, crystal-to-detector distance 5.00 cm.
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 on F2 against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
O1A0.09291 (5)0.27723 (10)0.31483 (5)0.0280 (2)0.828 (3)
O2A0.43766 (6)0.16711 (12)0.52414 (6)0.0379 (3)0.828 (3)
O3A0.37950 (6)−0.04279 (12)0.52952 (6)0.0417 (3)0.828 (3)
O4A0.27707 (6)0.55996 (11)0.39749 (6)0.0391 (3)0.828 (3)
O5A0.18713 (6)0.50849 (11)0.29870 (6)0.0372 (3)0.828 (3)
N1A0.37863 (7)0.08255 (13)0.50556 (6)0.0289 (3)0.828 (3)
N2A0.23146 (7)0.47265 (12)0.35751 (6)0.0272 (3)0.828 (3)
C1A0.15919 (8)0.23247 (15)0.35793 (10)0.0211 (4)0.828 (3)
C2A0.16612 (9)0.08529 (15)0.38681 (9)0.0229 (4)0.828 (3)
C3A0.23721 (9)0.03893 (16)0.43364 (10)0.0248 (4)0.828 (3)
H31A0.2404−0.05760.45240.030*0.828 (3)
C4A0.30549 (7)0.13271 (15)0.45422 (7)0.0245 (3)0.828 (3)
C5A0.30269 (7)0.27426 (15)0.42947 (7)0.0235 (3)0.828 (3)
H51A0.34830.33800.44520.028*0.828 (3)
C6A0.23184 (8)0.32142 (14)0.38106 (7)0.0234 (3)0.828 (3)
C7A0.09301 (9)−0.01813 (17)0.36283 (9)0.0273 (4)0.828 (3)
H71A0.04860.03580.32790.033*0.828 (3)
C8A0.05870 (16)−0.0639 (4)0.42727 (16)0.0404 (6)0.828 (3)
H81A0.0112−0.12830.41040.061*0.828 (3)
H82A0.04180.02350.44940.061*0.828 (3)
H83A0.1014−0.11570.46280.061*0.828 (3)
C9A0.11577 (11)−0.15163 (18)0.32438 (10)0.0328 (5)0.828 (3)
H91A0.1610−0.20490.35770.039*0.828 (3)
H92A0.0678−0.21800.31140.039*0.828 (3)
C10A0.1424 (2)−0.1119 (3)0.25677 (14)0.0392 (7)0.828 (3)
H11A0.1603−0.20040.23620.059*0.828 (3)
H12A0.1881−0.04210.26890.059*0.828 (3)
H13A0.0961−0.06780.22170.059*0.828 (3)
O1C0.09291 (5)0.27723 (10)0.31483 (5)0.0280 (2)0.172 (3)
O2C0.43766 (6)0.16711 (12)0.52414 (6)0.0379 (3)0.172 (3)
O3C0.37950 (6)−0.04279 (12)0.52952 (6)0.0417 (3)0.172 (3)
O4C0.27707 (6)0.55996 (11)0.39749 (6)0.0391 (3)0.172 (3)
O5C0.18713 (6)0.50849 (11)0.29870 (6)0.0372 (3)0.172 (3)
N1C0.37863 (7)0.08255 (13)0.50556 (6)0.0289 (3)0.172 (3)
N2C0.23146 (7)0.47265 (12)0.35751 (6)0.0272 (3)0.172 (3)
C1C0.1637 (2)0.2281 (3)0.3484 (4)0.0211 (4)0.172 (3)
C2C0.1743 (2)0.0761 (3)0.3713 (3)0.0229 (4)0.172 (3)
C3C0.2435 (3)0.0322 (3)0.4213 (4)0.0248 (4)0.172 (3)
H31C0.2499−0.06820.43420.030*0.172 (3)
C4C0.30549 (7)0.13271 (15)0.45422 (7)0.0245 (3)0.172 (3)
C5C0.30269 (7)0.27426 (15)0.42947 (7)0.0235 (3)0.172 (3)
H51C0.34830.33800.44520.028*0.172 (3)
C6C0.23184 (8)0.32142 (14)0.38106 (7)0.0234 (3)0.172 (3)
C7C0.1084 (3)−0.0307 (4)0.3324 (3)0.032 (2)*0.172 (3)
H7C0.05660.02710.31580.038*0.172 (3)
C8C0.1287 (9)−0.0929 (13)0.2640 (5)0.052 (7)*0.172 (3)
H81C0.1447−0.01280.23650.078*0.172 (3)
H82C0.0802−0.14240.23450.078*0.172 (3)
H83C0.1741−0.16290.27780.078*0.172 (3)
C9C0.0903 (4)−0.1504 (6)0.3806 (4)0.035 (2)*0.172 (3)
H91C0.1422−0.20100.40380.041*0.172 (3)
H92C0.0531−0.22290.35070.041*0.172 (3)
C10C0.0509 (13)−0.0946 (15)0.4387 (8)0.066 (7)*0.172 (3)
H11C0.0340−0.17780.46370.099*0.172 (3)
H12C0.0027−0.03520.41660.099*0.172 (3)
H13C0.0907−0.03490.47310.099*0.172 (3)
C1B−0.05882 (9)0.53181 (16)0.34180 (8)0.0342 (3)
H11B−0.02750.58640.31370.051*
H12B−0.03300.54410.39320.051*
H13B−0.11530.56890.33100.051*
N1B−0.05977 (7)0.37513 (12)0.32293 (7)0.0251 (3)
H1B−0.0076 (10)0.3408 (17)0.3347 (8)0.030*
H2B−0.0796 (9)0.3654 (17)0.2750 (9)0.030*
C2B−0.11157 (9)0.28503 (17)0.35852 (9)0.0365 (4)
H21B−0.10730.18190.34600.055*
H22B−0.16900.31670.34230.055*
H23B−0.09260.29700.41070.055*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O1A0.0194 (4)0.0320 (5)0.0310 (5)0.0004 (4)0.0034 (4)0.0035 (4)
O2A0.0232 (5)0.0452 (6)0.0406 (6)−0.0027 (4)−0.0006 (4)−0.0006 (5)
O3A0.0355 (6)0.0370 (6)0.0474 (7)0.0063 (5)0.0006 (5)0.0110 (5)
O4A0.0376 (6)0.0310 (6)0.0437 (6)−0.0147 (4)0.0011 (5)0.0020 (5)
O5A0.0393 (6)0.0334 (6)0.0339 (6)−0.0018 (4)−0.0004 (5)0.0087 (5)
N1A0.0243 (6)0.0345 (7)0.0278 (6)0.0046 (5)0.0065 (5)−0.0006 (5)
N2A0.0242 (5)0.0283 (6)0.0296 (6)−0.0040 (5)0.0076 (5)0.0019 (5)
C1A0.0201 (6)0.0256 (7)0.0194 (8)0.0007 (5)0.0084 (5)−0.0024 (5)
C2A0.0217 (7)0.0243 (7)0.0247 (9)−0.0007 (5)0.0095 (6)−0.0047 (6)
C3A0.0262 (7)0.0237 (7)0.0264 (9)0.0017 (5)0.0102 (6)−0.0006 (6)
C4A0.0207 (6)0.0303 (7)0.0223 (7)0.0034 (5)0.0054 (5)−0.0013 (5)
C5A0.0189 (6)0.0295 (7)0.0229 (7)−0.0033 (5)0.0069 (5)−0.0037 (5)
C6A0.0240 (6)0.0236 (6)0.0242 (7)−0.0009 (5)0.0092 (5)−0.0003 (5)
C7A0.0232 (8)0.0256 (9)0.0324 (10)−0.0048 (6)0.0057 (7)−0.0015 (7)
C8A0.0333 (12)0.0502 (13)0.0409 (13)−0.0134 (11)0.0153 (10)−0.0074 (12)
C9A0.0350 (9)0.0255 (9)0.0377 (10)−0.0074 (7)0.0089 (8)−0.0044 (7)
C10A0.0408 (13)0.0430 (13)0.0348 (13)−0.0144 (11)0.0114 (11)−0.0094 (10)
O1C0.0194 (4)0.0320 (5)0.0310 (5)0.0004 (4)0.0034 (4)0.0035 (4)
O2C0.0232 (5)0.0452 (6)0.0406 (6)−0.0027 (4)−0.0006 (4)−0.0006 (5)
O3C0.0355 (6)0.0370 (6)0.0474 (7)0.0063 (5)0.0006 (5)0.0110 (5)
O4C0.0376 (6)0.0310 (6)0.0437 (6)−0.0147 (4)0.0011 (5)0.0020 (5)
O5C0.0393 (6)0.0334 (6)0.0339 (6)−0.0018 (4)−0.0004 (5)0.0087 (5)
N1C0.0243 (6)0.0345 (7)0.0278 (6)0.0046 (5)0.0065 (5)−0.0006 (5)
N2C0.0242 (5)0.0283 (6)0.0296 (6)−0.0040 (5)0.0076 (5)0.0019 (5)
C1C0.0201 (6)0.0256 (7)0.0194 (8)0.0007 (5)0.0084 (5)−0.0024 (5)
C2C0.0217 (7)0.0243 (7)0.0247 (9)−0.0007 (5)0.0095 (6)−0.0047 (6)
C3C0.0262 (7)0.0237 (7)0.0264 (9)0.0017 (5)0.0102 (6)−0.0006 (6)
C4C0.0207 (6)0.0303 (7)0.0223 (7)0.0034 (5)0.0054 (5)−0.0013 (5)
C5C0.0189 (6)0.0295 (7)0.0229 (7)−0.0033 (5)0.0069 (5)−0.0037 (5)
C6C0.0240 (6)0.0236 (6)0.0242 (7)−0.0009 (5)0.0092 (5)−0.0003 (5)
C1B0.0378 (8)0.0301 (7)0.0324 (8)0.0000 (6)0.0046 (6)−0.0019 (6)
N1B0.0198 (5)0.0283 (6)0.0271 (6)0.0006 (4)0.0057 (5)0.0006 (5)
C2B0.0300 (7)0.0399 (8)0.0411 (9)−0.0055 (6)0.0117 (6)0.0058 (7)

Geometric parameters (Å, °)

O1A—C1A1.2770 (16)C10A—H13A0.9800
O2A—N1A1.2375 (15)C1C—C2C1.455 (2)
O3A—N1A1.2339 (15)C2C—C3C1.369 (2)
O4A—N2A1.2326 (15)C2C—C7C1.524 (3)
O5A—N2A1.2318 (15)C3C—H31C0.9500
N1A—C4A1.4440 (17)C7C—C9C1.514 (3)
N2A—C6A1.4546 (17)C7C—C8C1.547 (4)
C1A—C6A1.4412 (18)C7C—H7C1.0000
C1A—C2A1.4493 (19)C8C—H81C0.9800
C2A—C3A1.3700 (19)C8C—H82C0.9800
C2A—C7A1.5269 (19)C8C—H83C0.9800
C3A—C4A1.4073 (19)C9C—C10C1.520 (4)
C3A—H31A0.9500C9C—H91C0.9900
C4A—C5A1.3758 (19)C9C—H92C0.9900
C5A—C6A1.3830 (18)C10C—H11C0.9800
C5A—H51A0.9500C10C—H12C0.9800
C7A—C9A1.525 (2)C10C—H13C0.9800
C7A—C8A1.549 (4)C1B—N1B1.4771 (18)
C7A—H71A1.0000C1B—H11B0.9800
C8A—H81A0.9800C1B—H12B0.9800
C8A—H82A0.9800C1B—H13B0.9800
C8A—H83A0.9800N1B—C2B1.4845 (18)
C9A—C10A1.521 (3)N1B—H1B0.904 (16)
C9A—H91A0.9900N1B—H2B0.902 (17)
C9A—H92A0.9900C2B—H21B0.9800
C10A—H11A0.9800C2B—H22B0.9800
C10A—H12A0.9800C2B—H23B0.9800
O3A—N1A—O2A122.63 (12)C9C—C7C—C8C112.1 (3)
O3A—N1A—C4A118.58 (11)C2C—C7C—C8C111.4 (3)
O2A—N1A—C4A118.79 (12)C9C—C7C—H7C106.5
O5A—N2A—O4A122.53 (12)C2C—C7C—H7C106.5
O5A—N2A—C6A119.53 (11)C8C—C7C—H7C106.5
O4A—N2A—C6A117.93 (11)C7C—C8C—H81C109.5
O1A—C1A—C6A123.52 (12)C7C—C8C—H82C109.5
O1A—C1A—C2A121.27 (11)H81C—C8C—H82C109.5
C6A—C1A—C2A115.20 (11)C7C—C8C—H83C109.5
C3A—C2A—C1A120.79 (12)H81C—C8C—H83C109.5
C3A—C2A—C7A120.62 (13)H82C—C8C—H83C109.5
C1A—C2A—C7A118.59 (12)C7C—C9C—C10C113.5 (3)
C2A—C3A—C4A120.73 (13)C7C—C9C—H91C108.9
C2A—C3A—H31A119.6C10C—C9C—H91C108.9
C4A—C3A—H31A119.6C7C—C9C—H92C108.9
C5A—C4A—C3A121.43 (12)C10C—C9C—H92C108.9
C5A—C4A—N1A118.98 (12)H91C—C9C—H92C107.7
C3A—C4A—N1A119.49 (12)C9C—C10C—H11C109.5
C4A—C5A—C6A118.36 (12)C9C—C10C—H12C109.5
C4A—C5A—H51A120.8H11C—C10C—H12C109.5
C6A—C5A—H51A120.8C9C—C10C—H13C109.5
C5A—C6A—C1A123.42 (12)H11C—C10C—H13C109.5
C5A—C6A—N2A116.20 (11)H12C—C10C—H13C109.5
C1A—C6A—N2A120.23 (11)N1B—C1B—H11B109.5
C9A—C7A—C2A111.19 (13)N1B—C1B—H12B109.5
C9A—C7A—C8A111.13 (16)H11B—C1B—H12B109.5
C2A—C7A—C8A111.02 (16)N1B—C1B—H13B109.5
C9A—C7A—H71A107.8H11B—C1B—H13B109.5
C2A—C7A—H71A107.8H12B—C1B—H13B109.5
C8A—C7A—H71A107.8C1B—N1B—C2B113.36 (12)
C10A—C9A—C7A112.75 (19)C1B—N1B—H1B109.0 (10)
C10A—C9A—H91A109.0C2B—N1B—H1B109.6 (10)
C7A—C9A—H91A109.0C1B—N1B—H2B109.0 (10)
C10A—C9A—H92A109.0C2B—N1B—H2B107.9 (10)
C7A—C9A—H92A109.0H1B—N1B—H2B107.9 (14)
H91A—C9A—H92A107.8N1B—C2B—H21B109.5
C3C—C2C—C1C120.69 (19)N1B—C2B—H22B109.5
C3C—C2C—C7C122.7 (2)H21B—C2B—H22B109.5
C1C—C2C—C7C116.4 (2)N1B—C2B—H23B109.5
C2C—C3C—H31C119.2H21B—C2B—H23B109.5
C9C—C7C—C2C113.3 (3)H22B—C2B—H23B109.5
O1A—C1A—C2A—C3A−179.26 (17)O1A—C1A—C6A—N2A2.4 (3)
C6A—C1A—C2A—C3A1.1 (2)C2A—C1A—C6A—N2A−177.99 (13)
O1A—C1A—C2A—C7A1.9 (2)O5A—N2A—C6A—C5A154.19 (12)
C6A—C1A—C2A—C7A−177.74 (16)O4A—N2A—C6A—C5A−24.80 (17)
C1A—C2A—C3A—C4A−0.7 (2)O5A—N2A—C6A—C1A−30.0 (2)
C7A—C2A—C3A—C4A178.17 (17)O4A—N2A—C6A—C1A151.04 (15)
C2A—C3A—C4A—C5A1.4 (2)C3A—C2A—C7A—C9A−60.4 (2)
C2A—C3A—C4A—N1A177.89 (13)C1A—C2A—C7A—C9A118.50 (17)
O3A—N1A—C4A—C5A177.35 (12)C3A—C2A—C7A—C8A63.9 (2)
O2A—N1A—C4A—C5A−2.18 (18)C1A—C2A—C7A—C8A−117.23 (18)
O3A—N1A—C4A—C3A0.8 (2)C2A—C7A—C9A—C10A−61.0 (2)
O2A—N1A—C4A—C3A−178.72 (14)C8A—C7A—C9A—C10A174.80 (18)
C3A—C4A—C5A—C6A−2.7 (2)C3C—C2C—C7C—C9C40.3 (6)
N1A—C4A—C5A—C6A−179.14 (11)C1C—C2C—C7C—C9C−144.7 (5)
C4A—C5A—C6A—C1A3.3 (2)C3C—C2C—C7C—C8C−87.2 (7)
C4A—C5A—C6A—N2A178.96 (11)C1C—C2C—C7C—C8C87.8 (7)
O1A—C1A—C6A—C5A177.91 (15)C2C—C7C—C9C—C10C66.4 (11)
C2A—C1A—C6A—C5A−2.5 (2)C8C—C7C—C9C—C10C−166.5 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1B—H1B···O1A0.904 (16)1.914 (16)2.7585 (15)154.7 (14)
N1B—H2B···O1Ai0.902 (17)1.868 (17)2.7173 (16)156.2 (15)

Symmetry codes: (i) −x, y, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2194).

References

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