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Acta Cryst. (2009). E65, o2627    [ doi:10.1107/S160053680903921X ]

1-Decyloxy-4-nitrobenzene

X.-G. Yue

Abstract top

The title compound, C16H25NO3, has a zigzag decyloxy chain para to the nitro group of the aromatic ring. There are two independent molecules; the two rings are aligned at 48.15 (7)°. In the crystal, weak C-H...O hydrogen bonds lead to the formation of infinite chains.

Comment top

The hydroxy H atom of 4-nitropheno can be substituted by multifarious groups to form many ramifications(McBurney et al., 2004). We have synthesized the analogs using different alkyl as terminal groups and report here the molecular and crystal structures of the title compound, (I).

The title compound, (I), as shown in Fig. 1, crystallizes in space group P-1 and each asymmetric unit consists of two crystallographically independent 1-(decyloxy)-4-nitrobenzene. The angles of the two benzene rings (C1—C6 and C17—C22) in the same asymmetric unit is 48.15 (7) °. All nitryl oxygen atoms are engaged in C—H···O (2.53 (2), 2.60 (2), 2.70 (2), 2.77 (2), 2.79 (2) Å) hydrogen bonds. The weak C—H···O hydrogen bonds link the crystal into a two-dimensional network.

Related literature top

For structures of analogs of the title compound, see: McBurney et al. (2004)

Experimental top

1-(decyloxy)-4-nitrobenzene was prepared by adding 4-nitrophenol (0.14 g, 1 mmol), decyl iodide (0.27 g, 1 mmol) and acetone(15 ml) into 10 ml of 8% sodium hydroxide solution. The resultant mixture was heated for 2 h under reflux, then the solution was cooled to room temperaure in an ice bath with stirring. The colorless products were obtained by recrystallized the crude solid from 95% ethanol.

Refinement top

The benzene H atoms were treated as riding on their parent atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms attached to methylene were treated as riding on their parent atoms with C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C), instead with C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for methyl.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The asymmetric of title compound, with the atom numbering. Displacement ellipsoids of non-H atoms are drawn at the 30% probalility level.
1-Decyloxy-4-nitrobenzene top
Crystal data top
C16H25NO3Z = 4
Mr = 279.37F(000) = 608
Triclinic, P1Dx = 1.140 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.642 (3) ÅCell parameters from 9752 reflections
b = 16.065 (8) Åθ = 3.2–27.5°
c = 19.135 (7) ŵ = 0.08 mm−1
α = 107.410 (16)°T = 291 K
β = 90.610 (16)°Block, colorless
γ = 99.780 (18)°0.20 × 0.19 × 0.17 mm
V = 1627.4 (13) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer		7274 independent reflections
Radiation source: fine-focus sealed tube3970 reflections with I > 2σ(I)
graphiteRint = 0.030
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −7→7
Tmin = 0.984, Tmax = 0.987k = −20→20
15990 measured reflectionsl = −23→24
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176H-atom parameters constrained
S = 0.97 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
7274 reflections(Δ/σ)max < 0.001
363 parametersΔρmax = 0.18 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C16H25NO3γ = 99.780 (18)°
Mr = 279.37V = 1627.4 (13) Å3
Triclinic, P1Z = 4
a = 5.642 (3) ÅMo Kα radiation
b = 16.065 (8) ŵ = 0.08 mm−1
c = 19.135 (7) ÅT = 291 K
α = 107.410 (16)°0.20 × 0.19 × 0.17 mm
β = 90.610 (16)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer		7274 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		3970 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.987Rint = 0.030
15990 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.176Δρmax = 0.18 e Å−3
S = 0.97Δρmin = −0.17 e Å−3
7274 reflectionsAbsolute structure: ?
363 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
C11.0435 (3)−0.10617 (12)0.41928 (9)0.0498 (4)
C20.8180 (4)−0.14170 (12)0.38389 (10)0.0552 (5)
H20.7414−0.19820.38260.066*
C30.7089 (4)−0.09201 (13)0.35064 (10)0.0561 (5)
H30.5583−0.11550.32580.067*
C40.8218 (3)−0.00675 (12)0.35376 (9)0.0492 (4)
C51.0481 (3)0.02798 (12)0.38982 (9)0.0518 (4)
H51.12450.08480.39200.062*
C61.1591 (3)−0.02269 (13)0.42251 (9)0.0530 (5)
H61.3112−0.00020.44650.064*
C70.7923 (4)0.12696 (13)0.32581 (11)0.0622 (5)
H7A0.94860.13130.30520.075*
H7B0.81150.16280.37700.075*
C80.6180 (4)0.15878 (14)0.28437 (10)0.0608 (5)
H8A0.66850.22210.29340.073*
H8B0.46030.14940.30330.073*
C90.5963 (4)0.11315 (13)0.20197 (9)0.0557 (5)
H9A0.75390.12210.18280.067*
H9B0.54390.04990.19270.067*
C100.4209 (4)0.14703 (13)0.16135 (10)0.0562 (5)
H10A0.47050.21070.17240.067*
H10B0.26270.13630.17970.067*
C110.4007 (4)0.10524 (13)0.07868 (10)0.0575 (5)
H11A0.35070.04160.06740.069*
H11B0.55840.11610.06000.069*
C120.2237 (4)0.14028 (13)0.03955 (10)0.0569 (5)
H12A0.06590.12860.05790.068*
H12B0.27240.20410.05190.068*
C130.2023 (4)0.10103 (14)−0.04315 (10)0.0611 (5)
H13A0.15370.0372−0.05570.073*
H13B0.35950.1130−0.06180.073*
C140.0239 (4)0.13677 (14)−0.08081 (10)0.0591 (5)
H14A−0.13330.1241−0.06240.071*
H14B0.07150.2007−0.06730.071*
C150.0008 (4)0.10000 (17)−0.16340 (11)0.0763 (6)
H15A0.15770.1128−0.18200.092*
H15B−0.04710.0360−0.17710.092*
C16−0.1776 (5)0.13638 (19)−0.19974 (12)0.0838 (7)
H16A−0.33620.1198−0.18490.126*
H16B−0.17570.1127−0.25210.126*
H16C−0.13490.1999−0.18540.126*
C171.6603 (3)0.61062 (12)0.48056 (9)0.0483 (4)
C181.7118 (3)0.52982 (12)0.44104 (9)0.0515 (4)
H181.84240.50940.45590.062*
C191.5682 (3)0.47936 (12)0.37915 (9)0.0528 (5)
H191.60150.42460.35180.063*
C201.3741 (3)0.51059 (12)0.35782 (9)0.0485 (4)
C211.3281 (4)0.59306 (12)0.39760 (10)0.0550 (5)
H211.20020.61450.38240.066*
C221.4712 (3)0.64329 (12)0.45951 (10)0.0549 (5)
H221.44020.69850.48670.066*
C231.2354 (4)0.37683 (12)0.25940 (10)0.0599 (5)
H23A1.23080.34120.29240.072*
H23B1.38610.37570.23550.072*
C241.0252 (4)0.34081 (13)0.20304 (10)0.0597 (5)
H24A0.87760.34850.22780.072*
H24B1.01930.27760.18100.072*
C251.0330 (4)0.38395 (13)0.14233 (9)0.0577 (5)
H25A1.04120.44730.16410.069*
H25B1.17860.37520.11670.069*
C260.8174 (4)0.34758 (13)0.08732 (10)0.0596 (5)
H26A0.80710.28400.06670.072*
H26B0.67250.35750.11300.072*
C270.8234 (4)0.38781 (14)0.02524 (10)0.0636 (5)
H27A0.96630.3766−0.00120.076*
H27B0.83770.45160.04590.076*
C280.6052 (4)0.35306 (15)−0.02876 (11)0.0664 (6)
H28A0.59150.2893−0.04950.080*
H28B0.46250.3640−0.00220.080*
C290.6087 (4)0.39286 (17)−0.09064 (11)0.0740 (6)
H29A0.74860.3802−0.11810.089*
H29B0.62820.4568−0.06990.089*
C300.3882 (4)0.36084 (16)−0.14327 (11)0.0727 (6)
H30A0.36880.2969−0.16390.087*
H30B0.24850.3735−0.11570.087*
C310.3896 (5)0.3997 (2)−0.20473 (15)0.1040 (10)
H31A0.52280.3834−0.23430.125*
H31B0.42060.4638−0.18420.125*
C320.1645 (5)0.3727 (2)−0.25393 (14)0.0943 (8)
H32A0.12620.3092−0.27270.141*
H32B0.18840.3969−0.29400.141*
H32C0.03440.3947−0.22670.141*
N11.1571 (3)−0.15848 (12)0.45537 (9)0.0611 (4)
N21.8046 (3)0.66154 (12)0.54848 (8)0.0598 (4)
O11.0497 (3)−0.23246 (12)0.45217 (11)0.0953 (6)
O21.3531 (3)−0.12644 (11)0.48909 (9)0.0814 (5)
O30.6957 (2)0.03615 (9)0.31962 (7)0.0598 (4)
O41.9796 (3)0.63492 (11)0.56572 (8)0.0779 (5)
O51.7400 (3)0.72868 (11)0.58678 (8)0.0860 (5)
O61.2164 (2)0.46592 (9)0.29918 (7)0.0616 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0558 (11)0.0542 (11)0.0446 (9)0.0219 (9)0.0075 (8)0.0163 (7)
C20.0593 (12)0.0479 (11)0.0608 (11)0.0114 (9)0.0059 (9)0.0190 (8)
C30.0517 (11)0.0557 (12)0.0607 (11)0.0080 (9)−0.0042 (9)0.0188 (9)
C40.0543 (11)0.0536 (11)0.0428 (8)0.0139 (8)0.0003 (7)0.0174 (7)
C50.0569 (11)0.0500 (10)0.0489 (9)0.0059 (8)−0.0016 (8)0.0181 (8)
C60.0529 (11)0.0605 (12)0.0462 (9)0.0129 (9)−0.0013 (8)0.0161 (8)
C70.0787 (14)0.0553 (12)0.0549 (10)0.0099 (10)−0.0063 (10)0.0218 (9)
C80.0753 (14)0.0561 (12)0.0580 (10)0.0216 (10)0.0011 (9)0.0228 (9)
C90.0632 (12)0.0560 (11)0.0547 (10)0.0197 (9)0.0011 (9)0.0223 (8)
C100.0613 (12)0.0558 (11)0.0577 (10)0.0188 (9)0.0021 (9)0.0223 (9)
C110.0623 (12)0.0578 (12)0.0558 (10)0.0153 (9)−0.0008 (9)0.0204 (9)
C120.0581 (12)0.0610 (12)0.0553 (10)0.0159 (9)−0.0011 (9)0.0205 (9)
C130.0654 (13)0.0649 (13)0.0536 (10)0.0150 (10)−0.0033 (9)0.0171 (9)
C140.0568 (12)0.0652 (13)0.0553 (10)0.0105 (10)−0.0005 (9)0.0190 (9)
C150.0738 (15)0.0979 (18)0.0552 (11)0.0226 (13)−0.0071 (10)0.0168 (11)
C160.0803 (16)0.113 (2)0.0585 (12)0.0234 (14)−0.0106 (11)0.0247 (12)
C170.0491 (10)0.0482 (10)0.0461 (9)0.0050 (8)0.0005 (7)0.0142 (7)
C180.0495 (10)0.0560 (11)0.0525 (10)0.0140 (8)−0.0011 (8)0.0198 (8)
C190.0611 (12)0.0514 (11)0.0466 (9)0.0194 (9)0.0010 (8)0.0112 (8)
C200.0532 (11)0.0513 (10)0.0417 (8)0.0115 (8)−0.0008 (7)0.0144 (7)
C210.0553 (11)0.0543 (11)0.0569 (10)0.0189 (9)−0.0033 (8)0.0143 (8)
C220.0584 (11)0.0458 (10)0.0591 (10)0.0156 (8)0.0014 (9)0.0106 (8)
C230.0765 (14)0.0540 (11)0.0481 (9)0.0175 (10)−0.0059 (9)0.0112 (8)
C240.0676 (13)0.0561 (11)0.0509 (10)0.0060 (9)−0.0048 (9)0.0130 (8)
C250.0613 (12)0.0583 (12)0.0503 (10)0.0056 (9)−0.0032 (9)0.0150 (8)
C260.0608 (12)0.0626 (12)0.0521 (10)0.0029 (10)−0.0059 (9)0.0173 (9)
C270.0603 (13)0.0726 (14)0.0571 (11)0.0025 (10)−0.0061 (9)0.0239 (10)
C280.0628 (13)0.0753 (14)0.0598 (11)−0.0001 (11)−0.0096 (10)0.0261 (10)
C290.0664 (14)0.0923 (17)0.0672 (12)−0.0002 (12)−0.0090 (11)0.0387 (11)
C300.0696 (14)0.0848 (16)0.0630 (12)0.0045 (12)−0.0099 (10)0.0272 (11)
C310.0847 (18)0.150 (3)0.0893 (17)−0.0053 (17)−0.0188 (14)0.0705 (18)
C320.0967 (19)0.118 (2)0.0747 (15)0.0257 (16)−0.0117 (14)0.0354 (14)
N10.0681 (11)0.0645 (11)0.0604 (9)0.0272 (9)0.0088 (8)0.0251 (8)
N20.0583 (10)0.0597 (11)0.0558 (9)0.0045 (8)−0.0032 (8)0.0128 (8)
O10.1013 (13)0.0676 (11)0.1324 (14)0.0189 (9)−0.0091 (11)0.0523 (10)
O20.0739 (11)0.0946 (12)0.0890 (11)0.0244 (9)−0.0106 (9)0.0433 (9)
O30.0613 (8)0.0587 (8)0.0645 (8)0.0088 (6)−0.0112 (6)0.0279 (6)
O40.0709 (10)0.0857 (11)0.0717 (9)0.0151 (8)−0.0216 (8)0.0163 (8)
O50.0878 (12)0.0727 (11)0.0754 (10)0.0160 (9)−0.0120 (8)−0.0105 (8)
O60.0696 (9)0.0574 (8)0.0524 (7)0.0203 (6)−0.0148 (6)0.0047 (6)
Geometric parameters (Å, °) top
C1—C61.371 (3)C17—N21.462 (2)
C1—C21.381 (3)C18—C191.378 (2)
C1—N11.454 (2)C18—H180.9300
C2—C31.372 (3)C19—C201.385 (3)
C2—H20.9300C19—H190.9300
C3—C41.393 (3)C20—O61.359 (2)
C3—H30.9300C20—C211.385 (3)
C4—O31.354 (2)C21—C221.375 (2)
C4—C51.388 (3)C21—H210.9300
C5—C61.384 (2)C22—H220.9300
C5—H50.9300C23—O61.429 (2)
C6—H60.9300C23—C241.507 (3)
C7—O31.437 (2)C23—H23A0.9700
C7—C81.501 (3)C23—H23B0.9700
C7—H7A0.9700C24—C251.518 (3)
C7—H7B0.9700C24—H24A0.9700
C8—C91.521 (3)C24—H24B0.9700
C8—H8A0.9700C25—C261.514 (2)
C8—H8B0.9700C25—H25A0.9700
C9—C101.516 (2)C25—H25B0.9700
C9—H9A0.9700C26—C271.511 (3)
C9—H9B0.9700C26—H26A0.9700
C10—C111.517 (3)C26—H26B0.9700
C10—H10A0.9700C27—C281.513 (3)
C10—H10B0.9700C27—H27A0.9700
C11—C121.517 (3)C27—H27B0.9700
C11—H11A0.9700C28—C291.504 (3)
C11—H11B0.9700C28—H28A0.9700
C12—C131.513 (3)C28—H28B0.9700
C12—H12A0.9700C29—C301.507 (3)
C12—H12B0.9700C29—H29A0.9700
C13—C141.513 (3)C29—H29B0.9700
C13—H13A0.9700C30—C311.487 (3)
C13—H13B0.9700C30—H30A0.9700
C14—C151.508 (3)C30—H30B0.9700
C14—H14A0.9700C31—C321.494 (3)
C14—H14B0.9700C31—H31A0.9700
C15—C161.506 (3)C31—H31B0.9700
C15—H15A0.9700C32—H32A0.9600
C15—H15B0.9700C32—H32B0.9600
C16—H16A0.9600C32—H32C0.9600
C16—H16B0.9600N1—O11.222 (2)
C16—H16C0.9600N1—O21.223 (2)
C17—C221.373 (3)N2—O41.220 (2)
C17—C181.374 (3)N2—O51.225 (2)
C6—C1—C2121.73 (17)C17—C18—H18120.3
C6—C1—N1119.66 (17)C19—C18—H18120.3
C2—C1—N1118.59 (18)C18—C19—C20119.66 (18)
C3—C2—C1118.74 (18)C18—C19—H19120.2
C3—C2—H2120.6C20—C19—H19120.2
C1—C2—H2120.6O6—C20—C19124.99 (17)
C2—C3—C4120.55 (18)O6—C20—C21114.94 (16)
C2—C3—H3119.7C19—C20—C21120.08 (16)
C4—C3—H3119.7C22—C21—C20120.23 (17)
O3—C4—C5124.92 (17)C22—C21—H21119.9
O3—C4—C3115.19 (16)C20—C21—H21119.9
C5—C4—C3119.89 (17)C17—C22—C21118.89 (18)
C6—C5—C4119.46 (17)C17—C22—H22120.6
C6—C5—H5120.3C21—C22—H22120.6
C4—C5—H5120.3O6—C23—C24107.35 (16)
C1—C6—C5119.62 (17)O6—C23—H23A110.2
C1—C6—H6120.2C24—C23—H23A110.2
C5—C6—H6120.2O6—C23—H23B110.2
O3—C7—C8107.42 (16)C24—C23—H23B110.2
O3—C7—H7A110.2H23A—C23—H23B108.5
C8—C7—H7A110.2C23—C24—C25114.59 (17)
O3—C7—H7B110.2C23—C24—H24A108.6
C8—C7—H7B110.2C25—C24—H24A108.6
H7A—C7—H7B108.5C23—C24—H24B108.6
C7—C8—C9114.15 (17)C25—C24—H24B108.6
C7—C8—H8A108.7H24A—C24—H24B107.6
C9—C8—H8A108.7C26—C25—C24113.38 (16)
C7—C8—H8B108.7C26—C25—H25A108.9
C9—C8—H8B108.7C24—C25—H25A108.9
H8A—C8—H8B107.6C26—C25—H25B108.9
C10—C9—C8113.08 (16)C24—C25—H25B108.9
C10—C9—H9A109.0H25A—C25—H25B107.7
C8—C9—H9A109.0C27—C26—C25114.50 (16)
C10—C9—H9B109.0C27—C26—H26A108.6
C8—C9—H9B109.0C25—C26—H26A108.6
H9A—C9—H9B107.8C27—C26—H26B108.6
C9—C10—C11114.62 (16)C25—C26—H26B108.6
C9—C10—H10A108.6H26A—C26—H26B107.6
C11—C10—H10A108.6C26—C27—C28114.52 (17)
C9—C10—H10B108.6C26—C27—H27A108.6
C11—C10—H10B108.6C28—C27—H27A108.6
H10A—C10—H10B107.6C26—C27—H27B108.6
C10—C11—C12113.45 (17)C28—C27—H27B108.6
C10—C11—H11A108.9H27A—C27—H27B107.6
C12—C11—H11A108.9C29—C28—C27115.03 (17)
C10—C11—H11B108.9C29—C28—H28A108.5
C12—C11—H11B108.9C27—C28—H28A108.5
H11A—C11—H11B107.7C29—C28—H28B108.5
C13—C12—C11114.79 (17)C27—C28—H28B108.5
C13—C12—H12A108.6H28A—C28—H28B107.5
C11—C12—H12A108.6C28—C29—C30115.36 (18)
C13—C12—H12B108.6C28—C29—H29A108.4
C11—C12—H12B108.6C30—C29—H29A108.4
H12A—C12—H12B107.5C28—C29—H29B108.4
C12—C13—C14113.73 (17)C30—C29—H29B108.4
C12—C13—H13A108.8H29A—C29—H29B107.5
C14—C13—H13A108.8C31—C30—C29115.8 (2)
C12—C13—H13B108.8C31—C30—H30A108.3
C14—C13—H13B108.8C29—C30—H30A108.3
H13A—C13—H13B107.7C31—C30—H30B108.3
C15—C14—C13115.11 (18)C29—C30—H30B108.3
C15—C14—H14A108.5H30A—C30—H30B107.4
C13—C14—H14A108.5C30—C31—C32115.9 (2)
C15—C14—H14B108.5C30—C31—H31A108.3
C13—C14—H14B108.5C32—C31—H31A108.3
H14A—C14—H14B107.5C30—C31—H31B108.3
C16—C15—C14114.2 (2)C32—C31—H31B108.3
C16—C15—H15A108.7H31A—C31—H31B107.4
C14—C15—H15A108.7C31—C32—H32A109.5
C16—C15—H15B108.7C31—C32—H32B109.5
C14—C15—H15B108.7H32A—C32—H32B109.5
H15A—C15—H15B107.6C31—C32—H32C109.5
C15—C16—H16A109.5H32A—C32—H32C109.5
C15—C16—H16B109.5H32B—C32—H32C109.5
H16A—C16—H16B109.5O1—N1—O2122.39 (18)
C15—C16—H16C109.5O1—N1—C1118.43 (18)
H16A—C16—H16C109.5O2—N1—C1119.15 (18)
H16B—C16—H16C109.5O4—N2—O5122.67 (17)
C22—C17—C18121.79 (16)O4—N2—C17119.36 (18)
C22—C17—N2119.07 (17)O5—N2—C17117.95 (17)
C18—C17—N2119.10 (17)C4—O3—C7118.14 (14)
C17—C18—C19119.34 (17)C20—O6—C23118.71 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.932.533.378 (3)152
C7—H7B···O5ii0.972.773.263 (3)112
C18—H18···O4iii0.932.603.379 (3)141
C21—H21···O1iv0.932.703.346 (3)127
C22—H22···O1iv0.932.793.381 (3)123
Symmetry codes: (i) −x+3, −y, −z+1; (ii) −x+3, −y+1, −z+1; (iii) −x+4, −y+1, −z+1; (iv) x, y+1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.932.533.378 (3)152
C7—H7B···O5ii0.972.773.263 (3)112
C18—H18···O4iii0.932.603.379 (3)141
C21—H21···O1iv0.932.703.346 (3)127
C22—H22···O1iv0.932.793.381 (3)123
Symmetry codes: (i) −x+3, −y, −z+1; (ii) −x+3, −y+1, −z+1; (iii) −x+4, −y+1, −z+1; (iv) x, y+1, z.
references
References top

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.

McBurney, B., Foss, P. C. D., Reed, E. M., Shine, T. D., Glagovich, N. M., Westcott, B. L., Crundwell, G., Zeller, M. & Hunter, A. D. (2004). Acta Cryst. E60, o2179–o2180.

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.