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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3034.
Published online 2009 November 7. doi:  10.1107/S1600536809045966
PMCID: PMC2971973

1-Dodec­yloxy-4-nitro­benzene

Abstract

The asymmetric unit of the title compound, C18H29NO3, contains two independent mol­ecules. The benzene ring and the mean plane of the alkyl unit form dihedral angles of 83.69 (12) and 77.14 (11)° in the two mol­ecules. In the crystal structure, weak C—H(...)O hydrogen bonds link mol­ecules into double-layer ribbons extending in [110].

Related literature

For the structure of a related nitro­benzene derivative, see Yue (2009 [triangle]).

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Object name is e-65-o3034-scheme1.jpg

Experimental

Crystal data

  • C18H29NO3
  • M r = 307.42
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3034-efi1.jpg
  • a = 5.615 (3) Å
  • b = 16.064 (7) Å
  • c = 21.390 (12) Å
  • α = 72.190 (15)°
  • β = 87.290 (18)°
  • γ = 80.240 (16)°
  • V = 1810.1 (15) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 291 K
  • 0.23 × 0.23 × 0.21 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.983, T max = 0.984
  • 13636 measured reflections
  • 6158 independent reflections
  • 2548 reflections with I > 2σ(I)
  • R int = 0.064

Refinement

  • R[F 2 > 2σ(F 2)] = 0.068
  • wR(F 2) = 0.180
  • S = 0.99
  • 6158 reflections
  • 399 parameters
  • H-atom parameters constrained
  • Δρmax = 0.15 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045966/cv2628sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045966/cv2628Isup2.hkl

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

supplementary crystallographic information

Comment

Nitrobenzene and its derivatives are of great interest for their various applications. Recently, we reported the crystal structure of 1-decyloxy-4-nitrobenzene (Yue, 2009). As an extension of our work on the structure characterizations of nitrobenzene derivatives, we report herein the crystal structure of the title compound.

The title compound, as shown in Fig. 1, comprises two independent molecules in the asymmetric unit. Two benzene rings of the two molecules form a dihedral angle of 48.12 (13) °. Weak C—H···O hydrogen bonds (Table 1) link molecules into ribbons extended in direction [110].

Experimental

4-Nitrophenol (0.14 g, 1 mmol) and dodecyl iodide (0.30 g, 1 mmol) were dissovled in 15 ml of acetone. The sodium hydroxide solution (10 ml, 8%) was added into the above solution. The resultant mixture was heated for 2 h under refluxing and then the solution was cooled to room temperaure in an ice bath with stirring. The colourless crystals suitable for single-crystal analysis were obtained by recrystallization from 95% ethanol.

Refinement

H atoms were placed in calculated positions (C—H 0.93-0.97 Å) and were included in the refinement in the riding model with Uiso(H) = 1.2 or 1.5 Ueq(C).

Figures

Fig. 1.
Two independent molecules of the title compound showing the atom numbering and 30% probability displacement ellipsoids.

Crystal data

C18H29NO3Z = 4
Mr = 307.42F(000) = 672
Triclinic, P1Dx = 1.128 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.615 (3) ÅCell parameters from 8462 reflections
b = 16.064 (7) Åθ = 3.0–25.0°
c = 21.390 (12) ŵ = 0.08 mm1
α = 72.190 (15)°T = 291 K
β = 87.290 (18)°Block, colourless
γ = 80.240 (16)°0.23 × 0.23 × 0.21 mm
V = 1810.1 (15) Å3

Data collection

Rigaku R-AXIS RAPID diffractometer6158 independent reflections
Radiation source: fine-focus sealed tube2548 reflections with I > 2σ(I)
graphiteRint = 0.064
ω scansθmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −6→5
Tmin = 0.983, Tmax = 0.984k = −18→19
13636 measured reflectionsl = −25→25

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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0744P)2] where P = (Fo2 + 2Fc2)/3
6158 reflections(Δ/σ)max < 0.001
399 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = −0.16 e Å3

Special details

Experimental. (See detailed section in the paper)
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)

xyzUiso*/Ueq
C11.1633 (6)−0.1114 (2)0.98321 (16)0.0464 (9)
C20.9771 (7)−0.1433 (2)0.96353 (19)0.0577 (11)
H20.9392−0.19820.98770.069*
C30.8480 (7)−0.0939 (2)0.90832 (17)0.0544 (10)
H30.7243−0.11590.89430.065*
C40.9005 (6)−0.0111 (2)0.87311 (16)0.0482 (9)
C51.0903 (6)0.0201 (2)0.89214 (17)0.0513 (10)
H51.12900.07480.86780.062*
C61.2222 (7)−0.0301 (2)0.94732 (17)0.0548 (10)
H61.3504−0.00940.96050.066*
C70.7796 (7)0.1225 (2)0.78507 (17)0.0593 (11)
H7A0.93560.12400.76360.071*
H7B0.76790.15820.81470.071*
C80.5811 (7)0.1577 (2)0.73523 (17)0.0594 (11)
H8A0.57870.22090.71580.071*
H8B0.42830.14980.75750.071*
C90.5996 (7)0.1151 (2)0.68065 (17)0.0576 (11)
H9A0.60230.05190.69980.069*
H9B0.75110.12360.65780.069*
C100.3935 (7)0.1523 (2)0.63141 (17)0.0582 (10)
H10A0.24260.14270.65430.070*
H10B0.38860.21580.61320.070*
C110.4119 (7)0.1121 (2)0.57567 (18)0.0622 (11)
H11A0.56190.12250.55240.075*
H11B0.41900.04860.59390.075*
C120.2058 (7)0.1482 (2)0.52735 (18)0.0605 (11)
H12A0.19920.21180.50920.073*
H12B0.05610.13810.55080.073*
C130.2195 (7)0.1091 (2)0.47143 (19)0.0650 (11)
H13A0.36890.11940.44790.078*
H13B0.22700.04550.48960.078*
C140.0136 (7)0.1446 (3)0.42319 (19)0.0701 (12)
H14A0.00650.20810.40480.084*
H14B−0.13600.13440.44670.084*
C150.0286 (8)0.1047 (3)0.3678 (2)0.0761 (13)
H15A0.03990.04100.38630.091*
H15B0.17670.11600.34380.091*
C16−0.1797 (8)0.1382 (3)0.3197 (2)0.0740 (13)
H16A−0.32770.12730.34390.089*
H16B−0.19020.20190.30110.089*
C17−0.1683 (9)0.0991 (4)0.2650 (2)0.1038 (17)
H17A−0.14570.03510.28350.125*
H17B−0.02660.11380.23890.125*
C18−0.3825 (8)0.1275 (3)0.2203 (2)0.0944 (16)
H18A−0.51840.10350.24340.142*
H18B−0.34710.10620.18300.142*
H18C−0.42000.19100.20580.142*
C191.5593 (7)−0.3938 (2)0.92787 (16)0.0513 (10)
C201.6746 (7)−0.4774 (2)0.93077 (16)0.0531 (10)
H201.8218−0.50020.95260.064*
C211.5700 (7)−0.5274 (2)0.90099 (17)0.0531 (10)
H211.6470−0.58390.90220.064*
C221.3504 (7)−0.4930 (2)0.86934 (16)0.0513 (10)
C231.2366 (7)−0.4080 (2)0.86619 (18)0.0584 (11)
H231.0905−0.38460.84380.070*
C241.3406 (7)−0.3587 (2)0.89620 (17)0.0561 (10)
H241.2642−0.30220.89510.067*
C251.3257 (7)−0.6272 (2)0.84394 (18)0.0613 (11)
H25A1.3344−0.66280.88970.074*
H25B1.4870−0.63190.82560.074*
C261.1596 (7)−0.6589 (2)0.80708 (17)0.0622 (11)
H26A0.9977−0.64980.82440.075*
H26B1.2090−0.72210.81500.075*
C271.1516 (7)−0.6140 (2)0.73391 (17)0.0569 (11)
H27A1.3134−0.62270.71650.068*
H27B1.1005−0.55080.72580.068*
C280.9838 (7)−0.6477 (2)0.69766 (17)0.0577 (11)
H28A1.0324−0.71120.70730.069*
H28B0.8217−0.63750.71470.069*
C290.9752 (7)−0.6064 (2)0.62407 (17)0.0572 (11)
H29A1.1368−0.61650.60680.069*
H29B0.9256−0.54280.61420.069*
C300.8054 (7)−0.6419 (2)0.58938 (17)0.0588 (11)
H30A0.8532−0.70560.60010.071*
H30B0.6435−0.63070.60620.071*
C310.7980 (7)−0.6027 (2)0.51597 (18)0.0603 (11)
H31A0.9597−0.61380.49900.072*
H31B0.7495−0.53910.50510.072*
C320.6273 (7)−0.6392 (2)0.48198 (17)0.0577 (11)
H32A0.6749−0.70300.49350.069*
H32B0.4657−0.62760.49880.069*
C330.6188 (7)−0.6017 (2)0.40820 (17)0.0606 (11)
H33A0.7798−0.61410.39120.073*
H33B0.5733−0.53780.39660.073*
C340.4454 (7)−0.6375 (2)0.37487 (18)0.0613 (11)
H34A0.4905−0.70140.38680.074*
H34B0.2844−0.62490.39180.074*
C350.4363 (8)−0.6012 (3)0.30168 (19)0.0780 (13)
H35A0.5972−0.61370.28470.094*
H35B0.3903−0.53740.28960.094*
C360.2635 (8)−0.6377 (3)0.2690 (2)0.0848 (14)
H36A0.1016−0.62210.28300.127*
H36B0.3056−0.70110.28100.127*
H36C0.2735−0.61320.22220.127*
N11.2958 (6)−0.1617 (2)1.04342 (15)0.0629 (9)
N21.6664 (7)−0.3418 (3)0.96029 (16)0.0653 (10)
O11.2231 (5)−0.22878 (19)1.07737 (14)0.0902 (10)
O21.4686 (5)−0.13502 (17)1.05870 (13)0.0791 (9)
O30.7542 (5)0.03322 (15)0.82063 (12)0.0614 (7)
O41.5594 (6)−0.2675 (2)0.95704 (17)0.1001 (12)
O51.8548 (6)−0.37346 (19)0.99037 (15)0.0833 (10)
O61.2305 (4)−0.53613 (15)0.83828 (12)0.0608 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.049 (2)0.048 (2)0.040 (2)−0.0047 (18)−0.0020 (18)−0.0123 (16)
C20.058 (3)0.054 (2)0.063 (3)−0.018 (2)0.002 (2)−0.0157 (19)
C30.056 (3)0.056 (2)0.052 (2)−0.016 (2)−0.012 (2)−0.0131 (18)
C40.054 (2)0.054 (2)0.039 (2)−0.0096 (19)−0.0050 (19)−0.0157 (17)
C50.057 (3)0.054 (2)0.045 (2)−0.021 (2)−0.003 (2)−0.0119 (17)
C60.052 (2)0.065 (2)0.054 (3)−0.015 (2)−0.001 (2)−0.0240 (19)
C70.079 (3)0.054 (2)0.045 (2)−0.017 (2)−0.007 (2)−0.0109 (17)
C80.071 (3)0.056 (2)0.047 (2)−0.008 (2)−0.011 (2)−0.0102 (18)
C90.066 (3)0.064 (2)0.045 (2)−0.012 (2)−0.005 (2)−0.0184 (18)
C100.057 (3)0.066 (2)0.051 (2)−0.005 (2)−0.005 (2)−0.0178 (19)
C110.068 (3)0.070 (2)0.051 (2)−0.011 (2)−0.007 (2)−0.0208 (19)
C120.058 (3)0.075 (2)0.047 (2)−0.004 (2)−0.006 (2)−0.0195 (19)
C130.058 (3)0.082 (3)0.059 (3)0.000 (2)−0.012 (2)−0.032 (2)
C140.069 (3)0.086 (3)0.060 (3)−0.007 (2)−0.009 (2)−0.032 (2)
C150.075 (3)0.098 (3)0.062 (3)−0.010 (3)−0.015 (2)−0.035 (2)
C160.080 (3)0.086 (3)0.060 (3)−0.009 (2)−0.009 (2)−0.029 (2)
C170.092 (4)0.157 (4)0.083 (4)−0.005 (3)−0.019 (3)−0.071 (3)
C180.102 (4)0.119 (4)0.073 (3)−0.023 (3)−0.021 (3)−0.039 (3)
C190.063 (3)0.055 (2)0.042 (2)−0.022 (2)0.003 (2)−0.0170 (17)
C200.052 (2)0.066 (2)0.042 (2)−0.012 (2)−0.0028 (18)−0.0159 (18)
C210.053 (3)0.056 (2)0.051 (2)−0.0061 (19)−0.003 (2)−0.0186 (18)
C220.056 (3)0.060 (2)0.043 (2)−0.016 (2)0.0008 (19)−0.0193 (18)
C230.055 (3)0.060 (2)0.061 (3)−0.004 (2)−0.006 (2)−0.0212 (19)
C240.064 (3)0.049 (2)0.059 (3)−0.009 (2)0.004 (2)−0.0223 (18)
C250.077 (3)0.056 (2)0.053 (3)−0.007 (2)−0.009 (2)−0.0200 (18)
C260.078 (3)0.063 (2)0.053 (3)−0.021 (2)−0.003 (2)−0.0233 (19)
C270.066 (3)0.061 (2)0.050 (2)−0.019 (2)−0.003 (2)−0.0219 (18)
C280.061 (3)0.062 (2)0.055 (3)−0.018 (2)0.001 (2)−0.0221 (18)
C290.063 (3)0.065 (2)0.049 (2)−0.018 (2)−0.004 (2)−0.0201 (19)
C300.066 (3)0.062 (2)0.054 (3)−0.020 (2)−0.006 (2)−0.0199 (18)
C310.060 (3)0.065 (2)0.056 (3)−0.013 (2)−0.009 (2)−0.0158 (19)
C320.056 (3)0.064 (2)0.054 (3)−0.012 (2)−0.002 (2)−0.0179 (18)
C330.065 (3)0.071 (2)0.046 (2)−0.015 (2)−0.005 (2)−0.0155 (19)
C340.061 (3)0.074 (2)0.052 (3)−0.013 (2)−0.003 (2)−0.0228 (19)
C350.076 (3)0.110 (3)0.051 (3)−0.025 (3)−0.008 (2)−0.021 (2)
C360.074 (3)0.115 (3)0.067 (3)−0.015 (3)−0.019 (3)−0.028 (3)
N10.066 (2)0.070 (2)0.051 (2)−0.0071 (19)−0.0105 (18)−0.0163 (17)
N20.072 (3)0.074 (2)0.060 (2)−0.031 (2)0.004 (2)−0.0266 (19)
O10.093 (2)0.0818 (19)0.077 (2)−0.0241 (18)−0.0156 (18)0.0116 (16)
O20.080 (2)0.0864 (19)0.069 (2)−0.0167 (17)−0.0267 (17)−0.0151 (15)
O30.0731 (19)0.0588 (15)0.0521 (16)−0.0209 (14)−0.0134 (14)−0.0092 (12)
O40.107 (3)0.076 (2)0.136 (3)−0.015 (2)−0.021 (2)−0.056 (2)
O50.077 (2)0.098 (2)0.090 (2)−0.0213 (18)−0.0191 (19)−0.0434 (17)
O60.0667 (18)0.0597 (15)0.0628 (17)−0.0066 (14)−0.0164 (14)−0.0282 (12)

Geometric parameters (Å, °)

C1—C21.373 (4)C19—N21.451 (4)
C1—C61.384 (4)C20—C211.380 (4)
C1—N11.454 (4)C20—H200.9300
C2—C31.365 (4)C21—C221.379 (5)
C2—H20.9300C21—H210.9300
C3—C41.387 (4)C22—O61.362 (4)
C3—H30.9300C22—C231.389 (5)
C4—O31.357 (4)C23—C241.373 (4)
C4—C51.378 (4)C23—H230.9300
C5—C61.374 (4)C24—H240.9300
C5—H50.9300C25—O61.440 (4)
C6—H60.9300C25—C261.492 (4)
C7—O31.432 (3)C25—H25A0.9700
C7—C81.492 (4)C25—H25B0.9700
C7—H7A0.9700C26—C271.509 (5)
C7—H7B0.9700C26—H26A0.9700
C8—C91.515 (5)C26—H26B0.9700
C8—H8A0.9700C27—C281.510 (4)
C8—H8B0.9700C27—H27A0.9700
C9—C101.517 (4)C27—H27B0.9700
C9—H9A0.9700C28—C291.509 (4)
C9—H9B0.9700C28—H28A0.9700
C10—C111.512 (5)C28—H28B0.9700
C10—H10A0.9700C29—C301.515 (4)
C10—H10B0.9700C29—H29A0.9700
C11—C121.504 (5)C29—H29B0.9700
C11—H11A0.9700C30—C311.502 (5)
C11—H11B0.9700C30—H30A0.9700
C12—C131.506 (5)C30—H30B0.9700
C12—H12A0.9700C31—C321.519 (4)
C12—H12B0.9700C31—H31A0.9700
C13—C141.502 (5)C31—H31B0.9700
C13—H13A0.9700C32—C331.507 (5)
C13—H13B0.9700C32—H32A0.9700
C14—C151.503 (5)C32—H32B0.9700
C14—H14A0.9700C33—C341.514 (4)
C14—H14B0.9700C33—H33A0.9700
C15—C161.508 (5)C33—H33B0.9700
C15—H15A0.9700C34—C351.494 (5)
C15—H15B0.9700C34—H34A0.9700
C16—C171.483 (6)C34—H34B0.9700
C16—H16A0.9700C35—C361.510 (5)
C16—H16B0.9700C35—H35A0.9700
C17—C181.491 (5)C35—H35B0.9700
C17—H17A0.9700C36—H36A0.9600
C17—H17B0.9700C36—H36B0.9600
C18—H18A0.9600C36—H36C0.9600
C18—H18B0.9600N1—O21.220 (3)
C18—H18C0.9600N1—O11.224 (3)
C19—C201.373 (5)N2—O51.214 (4)
C19—C241.377 (5)N2—O41.225 (4)
C2—C1—C6120.6 (3)C19—C20—H20120.3
C2—C1—N1120.2 (3)C21—C20—H20120.3
C6—C1—N1119.2 (3)C22—C21—C20119.6 (4)
C3—C2—C1119.6 (3)C22—C21—H21120.2
C3—C2—H2120.2C20—C21—H21120.2
C1—C2—H2120.2O6—C22—C21124.7 (3)
C2—C3—C4120.2 (3)O6—C22—C23114.8 (3)
C2—C3—H3119.9C21—C22—C23120.5 (3)
C4—C3—H3119.9C24—C23—C22119.7 (4)
O3—C4—C5125.0 (3)C24—C23—H23120.1
O3—C4—C3114.9 (3)C22—C23—H23120.1
C5—C4—C3120.1 (3)C23—C24—C19119.3 (4)
C6—C5—C4119.7 (3)C23—C24—H24120.4
C6—C5—H5120.2C19—C24—H24120.4
C4—C5—H5120.2O6—C25—C26107.4 (3)
C5—C6—C1119.7 (3)O6—C25—H25A110.2
C5—C6—H6120.1C26—C25—H25A110.2
C1—C6—H6120.1O6—C25—H25B110.2
O3—C7—C8107.4 (3)C26—C25—H25B110.2
O3—C7—H7A110.2H25A—C25—H25B108.5
C8—C7—H7A110.2C25—C26—C27114.7 (3)
O3—C7—H7B110.2C25—C26—H26A108.6
C8—C7—H7B110.2C27—C26—H26A108.6
H7A—C7—H7B108.5C25—C26—H26B108.6
C7—C8—C9115.1 (3)C27—C26—H26B108.6
C7—C8—H8A108.5H26A—C26—H26B107.6
C9—C8—H8A108.5C26—C27—C28113.6 (3)
C7—C8—H8B108.5C26—C27—H27A108.8
C9—C8—H8B108.5C28—C27—H27A108.8
H8A—C8—H8B107.5C26—C27—H27B108.8
C8—C9—C10113.3 (3)C28—C27—H27B108.8
C8—C9—H9A108.9H27A—C27—H27B107.7
C10—C9—H9A108.9C29—C28—C27115.5 (3)
C8—C9—H9B108.9C29—C28—H28A108.4
C10—C9—H9B108.9C27—C28—H28A108.4
H9A—C9—H9B107.7C29—C28—H28B108.4
C11—C10—C9114.1 (3)C27—C28—H28B108.4
C11—C10—H10A108.7H28A—C28—H28B107.5
C9—C10—H10A108.7C28—C29—C30114.0 (3)
C11—C10—H10B108.7C28—C29—H29A108.8
C9—C10—H10B108.7C30—C29—H29A108.8
H10A—C10—H10B107.6C28—C29—H29B108.8
C12—C11—C10114.1 (3)C30—C29—H29B108.8
C12—C11—H11A108.7H29A—C29—H29B107.7
C10—C11—H11A108.7C31—C30—C29114.7 (3)
C12—C11—H11B108.7C31—C30—H30A108.6
C10—C11—H11B108.7C29—C30—H30A108.6
H11A—C11—H11B107.6C31—C30—H30B108.6
C11—C12—C13115.1 (3)C29—C30—H30B108.6
C11—C12—H12A108.5H30A—C30—H30B107.6
C13—C12—H12A108.5C30—C31—C32114.0 (3)
C11—C12—H12B108.5C30—C31—H31A108.7
C13—C12—H12B108.5C32—C31—H31A108.7
H12A—C12—H12B107.5C30—C31—H31B108.7
C14—C13—C12115.4 (4)C32—C31—H31B108.7
C14—C13—H13A108.4H31A—C31—H31B107.6
C12—C13—H13A108.4C33—C32—C31115.1 (3)
C14—C13—H13B108.4C33—C32—H32A108.5
C12—C13—H13B108.4C31—C32—H32A108.5
H13A—C13—H13B107.5C33—C32—H32B108.5
C13—C14—C15114.9 (4)C31—C32—H32B108.5
C13—C14—H14A108.5H32A—C32—H32B107.5
C15—C14—H14A108.5C32—C33—C34114.7 (3)
C13—C14—H14B108.5C32—C33—H33A108.6
C15—C14—H14B108.5C34—C33—H33A108.6
H14A—C14—H14B107.5C32—C33—H33B108.6
C14—C15—C16115.5 (4)C34—C33—H33B108.6
C14—C15—H15A108.4H33A—C33—H33B107.6
C16—C15—H15A108.4C35—C34—C33115.2 (3)
C14—C15—H15B108.4C35—C34—H34A108.5
C16—C15—H15B108.4C33—C34—H34A108.5
H15A—C15—H15B107.5C35—C34—H34B108.5
C17—C16—C15116.2 (4)C33—C34—H34B108.5
C17—C16—H16A108.2H34A—C34—H34B107.5
C15—C16—H16A108.2C34—C35—C36114.7 (3)
C17—C16—H16B108.2C34—C35—H35A108.6
C15—C16—H16B108.2C36—C35—H35A108.6
H16A—C16—H16B107.4C34—C35—H35B108.6
C16—C17—C18116.1 (4)C36—C35—H35B108.6
C16—C17—H17A108.3H35A—C35—H35B107.6
C18—C17—H17A108.3C35—C36—H36A109.5
C16—C17—H17B108.3C35—C36—H36B109.5
C18—C17—H17B108.3H36A—C36—H36B109.5
H17A—C17—H17B107.4C35—C36—H36C109.5
C17—C18—H18A109.5H36A—C36—H36C109.5
C17—C18—H18B109.5H36B—C36—H36C109.5
H18A—C18—H18B109.5O2—N1—O1123.0 (3)
C17—C18—H18C109.5O2—N1—C1119.6 (3)
H18A—C18—H18C109.5O1—N1—C1117.4 (3)
H18B—C18—H18C109.5O5—N2—O4122.5 (3)
C20—C19—C24121.5 (3)O5—N2—C19119.4 (4)
C20—C19—N2119.5 (4)O4—N2—C19118.1 (4)
C24—C19—N2118.9 (4)C4—O3—C7118.9 (2)
C19—C20—C21119.4 (3)C22—O6—C25118.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···O4i0.932.693.329 (4)127
C6—H6···O2ii0.932.603.375 (4)141
C20—H20···O5iii0.932.523.372 (5)152

Symmetry codes: (i) x−1, y, z; (ii) −x+3, −y, −z+2; (iii) −x+4, −y−1, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2628).

References

  • Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
  • Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Yue, X.-G. (2009). Acta Cryst. E65, o2627. [PMC free article] [PubMed]

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