1-Dec­yloxy-4-nitro­benzene

Yue, X.-G

doi:10.1107/S160053680903921X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page o2627

https://doi.org/10.1107/S160053680903921X

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1-Decyloxy-4-nitrobenzene

Xi-Gui Yue ^a ^*

^aAlan G. MacDiarmid Institute, Jilin University, Changchun 130012, People's Republic of China
^*Correspondence e-mail: yuexigui@jlu.edu.cn

(Received 17 September 2009; accepted 27 September 2009; online 3 October 2009)

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.

Related literature

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

Experimental

Crystal data

C₁₆H₂₅NO₃
M_r = 279.37
Triclinic, $[P \overline 1]$
a = 5.642 (3) Å
b = 16.065 (8) Å
c = 19.135 (7) Å
α = 107.410 (16)°
β = 90.610 (16)°
γ = 99.780 (18)°
V = 1627.4 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 291 K
0.20 × 0.19 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.984, T_max = 0.987
15990 measured reflections
7274 independent reflections
3970 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.176
S = 0.97
7274 reflections
363 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2ⁱ	0.93	2.53	3.378 (3)	152
C7—H7B⋯O5ⁱⁱ	0.97	2.77	3.263 (3)	112
C18—H18⋯O4ⁱⁱⁱ	0.93	2.60	3.379 (3)	141
C21—H21⋯O1^iv	0.93	2.70	3.346 (3)	127
C22—H22⋯O1^iv	0.93	2.79	3.381 (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.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680903921X/ng2644sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680903921X/ng2644Isup2.hkl

checkCIF report

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.

Structure description top

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

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

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

C₁₆H₂₅NO₃	Z = 4
M_r = 279.37	F(000) = 608
Triclinic, P1	D_x = 1.140 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.642 (3) Å	Cell parameters from 9752 reflections
b = 16.065 (8) Å	θ = 3.2–27.5°
c = 19.135 (7) Å	µ = 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 tube	3970 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→7
T_min = 0.984, T_max = 0.987	k = −20→20
15990 measured reflections	l = −23→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
7274 reflections	(Δ/σ)_max < 0.001
363 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₆H₂₅NO₃	γ = 99.780 (18)°
M_r = 279.37	V = 1627.4 (13) Å³
Triclinic, P1	Z = 4
a = 5.642 (3) Å	Mo Kα radiation
b = 16.065 (8) Å	µ = 0.08 mm⁻¹
c = 19.135 (7) Å	T = 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)
T_min = 0.984, T_max = 0.987	R_int = 0.030
15990 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 0.97	Δρ_max = 0.18 e Å⁻³
7274 reflections	Δρ_min = −0.17 e Å⁻³
363 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

	x	y	z	U_iso*/U_eq
C1	1.0435 (3)	−0.10617 (12)	0.41928 (9)	0.0498 (4)
C2	0.8180 (4)	−0.14170 (12)	0.38389 (10)	0.0552 (5)
H2	0.7414	−0.1982	0.3826	0.066*
C3	0.7089 (4)	−0.09201 (13)	0.35064 (10)	0.0561 (5)
H3	0.5583	−0.1155	0.3258	0.067*
C4	0.8218 (3)	−0.00675 (12)	0.35376 (9)	0.0492 (4)
C5	1.0481 (3)	0.02798 (12)	0.38982 (9)	0.0518 (4)
H5	1.1245	0.0848	0.3920	0.062*
C6	1.1591 (3)	−0.02269 (13)	0.42251 (9)	0.0530 (5)
H6	1.3112	−0.0002	0.4465	0.064*
C7	0.7923 (4)	0.12696 (13)	0.32581 (11)	0.0622 (5)
H7A	0.9486	0.1313	0.3052	0.075*
H7B	0.8115	0.1628	0.3770	0.075*
C8	0.6180 (4)	0.15878 (14)	0.28437 (10)	0.0608 (5)
H8A	0.6685	0.2221	0.2934	0.073*
H8B	0.4603	0.1494	0.3033	0.073*
C9	0.5963 (4)	0.11315 (13)	0.20197 (9)	0.0557 (5)
H9A	0.7539	0.1221	0.1828	0.067*
H9B	0.5439	0.0499	0.1927	0.067*
C10	0.4209 (4)	0.14703 (13)	0.16135 (10)	0.0562 (5)
H10A	0.4705	0.2107	0.1724	0.067*
H10B	0.2627	0.1363	0.1797	0.067*
C11	0.4007 (4)	0.10524 (13)	0.07868 (10)	0.0575 (5)
H11A	0.3507	0.0416	0.0674	0.069*
H11B	0.5584	0.1161	0.0600	0.069*
C12	0.2237 (4)	0.14028 (13)	0.03955 (10)	0.0569 (5)
H12A	0.0659	0.1286	0.0579	0.068*
H12B	0.2724	0.2041	0.0519	0.068*
C13	0.2023 (4)	0.10103 (14)	−0.04315 (10)	0.0611 (5)
H13A	0.1537	0.0372	−0.0557	0.073*
H13B	0.3595	0.1130	−0.0618	0.073*
C14	0.0239 (4)	0.13677 (14)	−0.08081 (10)	0.0591 (5)
H14A	−0.1333	0.1241	−0.0624	0.071*
H14B	0.0715	0.2007	−0.0673	0.071*
C15	0.0008 (4)	0.10000 (17)	−0.16340 (11)	0.0763 (6)
H15A	0.1577	0.1128	−0.1820	0.092*
H15B	−0.0471	0.0360	−0.1771	0.092*
C16	−0.1776 (5)	0.13638 (19)	−0.19974 (12)	0.0838 (7)
H16A	−0.3362	0.1198	−0.1849	0.126*
H16B	−0.1757	0.1127	−0.2521	0.126*
H16C	−0.1349	0.1999	−0.1854	0.126*
C17	1.6603 (3)	0.61062 (12)	0.48056 (9)	0.0483 (4)
C18	1.7118 (3)	0.52982 (12)	0.44104 (9)	0.0515 (4)
H18	1.8424	0.5094	0.4559	0.062*
C19	1.5682 (3)	0.47936 (12)	0.37915 (9)	0.0528 (5)
H19	1.6015	0.4246	0.3518	0.063*
C20	1.3741 (3)	0.51059 (12)	0.35782 (9)	0.0485 (4)
C21	1.3281 (4)	0.59306 (12)	0.39760 (10)	0.0550 (5)
H21	1.2002	0.6145	0.3824	0.066*
C22	1.4712 (3)	0.64329 (12)	0.45951 (10)	0.0549 (5)
H22	1.4402	0.6985	0.4867	0.066*
C23	1.2354 (4)	0.37683 (12)	0.25940 (10)	0.0599 (5)
H23A	1.2308	0.3412	0.2924	0.072*
H23B	1.3861	0.3757	0.2355	0.072*
C24	1.0252 (4)	0.34081 (13)	0.20304 (10)	0.0597 (5)
H24A	0.8776	0.3485	0.2278	0.072*
H24B	1.0193	0.2776	0.1810	0.072*
C25	1.0330 (4)	0.38395 (13)	0.14233 (9)	0.0577 (5)
H25A	1.0412	0.4473	0.1641	0.069*
H25B	1.1786	0.3752	0.1167	0.069*
C26	0.8174 (4)	0.34758 (13)	0.08732 (10)	0.0596 (5)
H26A	0.8071	0.2840	0.0667	0.072*
H26B	0.6725	0.3575	0.1130	0.072*
C27	0.8234 (4)	0.38781 (14)	0.02524 (10)	0.0636 (5)
H27A	0.9663	0.3766	−0.0012	0.076*
H27B	0.8377	0.4516	0.0459	0.076*
C28	0.6052 (4)	0.35306 (15)	−0.02876 (11)	0.0664 (6)
H28A	0.5915	0.2893	−0.0495	0.080*
H28B	0.4625	0.3640	−0.0022	0.080*
C29	0.6087 (4)	0.39286 (17)	−0.09064 (11)	0.0740 (6)
H29A	0.7486	0.3802	−0.1181	0.089*
H29B	0.6282	0.4568	−0.0699	0.089*
C30	0.3882 (4)	0.36084 (16)	−0.14327 (11)	0.0727 (6)
H30A	0.3688	0.2969	−0.1639	0.087*
H30B	0.2485	0.3735	−0.1157	0.087*
C31	0.3896 (5)	0.3997 (2)	−0.20473 (15)	0.1040 (10)
H31A	0.5228	0.3834	−0.2343	0.125*
H31B	0.4206	0.4638	−0.1842	0.125*
C32	0.1645 (5)	0.3727 (2)	−0.25393 (14)	0.0943 (8)
H32A	0.1262	0.3092	−0.2727	0.141*
H32B	0.1884	0.3969	−0.2940	0.141*
H32C	0.0344	0.3947	−0.2267	0.141*
N1	1.1571 (3)	−0.15848 (12)	0.45537 (9)	0.0611 (4)
N2	1.8046 (3)	0.66154 (12)	0.54848 (8)	0.0598 (4)
O1	1.0497 (3)	−0.23246 (12)	0.45217 (11)	0.0953 (6)
O2	1.3531 (3)	−0.12644 (11)	0.48909 (9)	0.0814 (5)
O3	0.6957 (2)	0.03615 (9)	0.31962 (7)	0.0598 (4)
O4	1.9796 (3)	0.63492 (11)	0.56572 (8)	0.0779 (5)
O5	1.7400 (3)	0.72868 (11)	0.58678 (8)	0.0860 (5)
O6	1.2164 (2)	0.46592 (9)	0.29918 (7)	0.0616 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0558 (11)	0.0542 (11)	0.0446 (9)	0.0219 (9)	0.0075 (8)	0.0163 (7)
C2	0.0593 (12)	0.0479 (11)	0.0608 (11)	0.0114 (9)	0.0059 (9)	0.0190 (8)
C3	0.0517 (11)	0.0557 (12)	0.0607 (11)	0.0080 (9)	−0.0042 (9)	0.0188 (9)
C4	0.0543 (11)	0.0536 (11)	0.0428 (8)	0.0139 (8)	0.0003 (7)	0.0174 (7)
C5	0.0569 (11)	0.0500 (10)	0.0489 (9)	0.0059 (8)	−0.0016 (8)	0.0181 (8)
C6	0.0529 (11)	0.0605 (12)	0.0462 (9)	0.0129 (9)	−0.0013 (8)	0.0161 (8)
C7	0.0787 (14)	0.0553 (12)	0.0549 (10)	0.0099 (10)	−0.0063 (10)	0.0218 (9)
C8	0.0753 (14)	0.0561 (12)	0.0580 (10)	0.0216 (10)	0.0011 (9)	0.0228 (9)
C9	0.0632 (12)	0.0560 (11)	0.0547 (10)	0.0197 (9)	0.0011 (9)	0.0223 (8)
C10	0.0613 (12)	0.0558 (11)	0.0577 (10)	0.0188 (9)	0.0021 (9)	0.0223 (9)
C11	0.0623 (12)	0.0578 (12)	0.0558 (10)	0.0153 (9)	−0.0008 (9)	0.0204 (9)
C12	0.0581 (12)	0.0610 (12)	0.0553 (10)	0.0159 (9)	−0.0011 (9)	0.0205 (9)
C13	0.0654 (13)	0.0649 (13)	0.0536 (10)	0.0150 (10)	−0.0033 (9)	0.0171 (9)
C14	0.0568 (12)	0.0652 (13)	0.0553 (10)	0.0105 (10)	−0.0005 (9)	0.0190 (9)
C15	0.0738 (15)	0.0979 (18)	0.0552 (11)	0.0226 (13)	−0.0071 (10)	0.0168 (11)
C16	0.0803 (16)	0.113 (2)	0.0585 (12)	0.0234 (14)	−0.0106 (11)	0.0247 (12)
C17	0.0491 (10)	0.0482 (10)	0.0461 (9)	0.0050 (8)	0.0005 (7)	0.0142 (7)
C18	0.0495 (10)	0.0560 (11)	0.0525 (10)	0.0140 (8)	−0.0011 (8)	0.0198 (8)
C19	0.0611 (12)	0.0514 (11)	0.0466 (9)	0.0194 (9)	0.0010 (8)	0.0112 (8)
C20	0.0532 (11)	0.0513 (10)	0.0417 (8)	0.0115 (8)	−0.0008 (7)	0.0144 (7)
C21	0.0553 (11)	0.0543 (11)	0.0569 (10)	0.0189 (9)	−0.0033 (8)	0.0143 (8)
C22	0.0584 (11)	0.0458 (10)	0.0591 (10)	0.0156 (8)	0.0014 (9)	0.0106 (8)
C23	0.0765 (14)	0.0540 (11)	0.0481 (9)	0.0175 (10)	−0.0059 (9)	0.0112 (8)
C24	0.0676 (13)	0.0561 (11)	0.0509 (10)	0.0060 (9)	−0.0048 (9)	0.0130 (8)
C25	0.0613 (12)	0.0583 (12)	0.0503 (10)	0.0056 (9)	−0.0032 (9)	0.0150 (8)
C26	0.0608 (12)	0.0626 (12)	0.0521 (10)	0.0029 (10)	−0.0059 (9)	0.0173 (9)
C27	0.0603 (13)	0.0726 (14)	0.0571 (11)	0.0025 (10)	−0.0061 (9)	0.0239 (10)
C28	0.0628 (13)	0.0753 (14)	0.0598 (11)	−0.0001 (11)	−0.0096 (10)	0.0261 (10)
C29	0.0664 (14)	0.0923 (17)	0.0672 (12)	−0.0002 (12)	−0.0090 (11)	0.0387 (11)
C30	0.0696 (14)	0.0848 (16)	0.0630 (12)	0.0045 (12)	−0.0099 (10)	0.0272 (11)
C31	0.0847 (18)	0.150 (3)	0.0893 (17)	−0.0053 (17)	−0.0188 (14)	0.0705 (18)
C32	0.0967 (19)	0.118 (2)	0.0747 (15)	0.0257 (16)	−0.0117 (14)	0.0354 (14)
N1	0.0681 (11)	0.0645 (11)	0.0604 (9)	0.0272 (9)	0.0088 (8)	0.0251 (8)
N2	0.0583 (10)	0.0597 (11)	0.0558 (9)	0.0045 (8)	−0.0032 (8)	0.0128 (8)
O1	0.1013 (13)	0.0676 (11)	0.1324 (14)	0.0189 (9)	−0.0091 (11)	0.0523 (10)
O2	0.0739 (11)	0.0946 (12)	0.0890 (11)	0.0244 (9)	−0.0106 (9)	0.0433 (9)
O3	0.0613 (8)	0.0587 (8)	0.0645 (8)	0.0088 (6)	−0.0112 (6)	0.0279 (6)
O4	0.0709 (10)	0.0857 (11)	0.0717 (9)	0.0151 (8)	−0.0216 (8)	0.0163 (8)
O5	0.0878 (12)	0.0727 (11)	0.0754 (10)	0.0160 (9)	−0.0120 (8)	−0.0105 (8)
O6	0.0696 (9)	0.0574 (8)	0.0524 (7)	0.0203 (6)	−0.0148 (6)	0.0047 (6)

Geometric parameters (Å, º) top

C1—C6	1.371 (3)	C17—N2	1.462 (2)
C1—C2	1.381 (3)	C18—C19	1.378 (2)
C1—N1	1.454 (2)	C18—H18	0.9300
C2—C3	1.372 (3)	C19—C20	1.385 (3)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.393 (3)	C20—O6	1.359 (2)
C3—H3	0.9300	C20—C21	1.385 (3)
C4—O3	1.354 (2)	C21—C22	1.375 (2)
C4—C5	1.388 (3)	C21—H21	0.9300
C5—C6	1.384 (2)	C22—H22	0.9300
C5—H5	0.9300	C23—O6	1.429 (2)
C6—H6	0.9300	C23—C24	1.507 (3)
C7—O3	1.437 (2)	C23—H23A	0.9700
C7—C8	1.501 (3)	C23—H23B	0.9700
C7—H7A	0.9700	C24—C25	1.518 (3)
C7—H7B	0.9700	C24—H24A	0.9700
C8—C9	1.521 (3)	C24—H24B	0.9700
C8—H8A	0.9700	C25—C26	1.514 (2)
C8—H8B	0.9700	C25—H25A	0.9700
C9—C10	1.516 (2)	C25—H25B	0.9700
C9—H9A	0.9700	C26—C27	1.511 (3)
C9—H9B	0.9700	C26—H26A	0.9700
C10—C11	1.517 (3)	C26—H26B	0.9700
C10—H10A	0.9700	C27—C28	1.513 (3)
C10—H10B	0.9700	C27—H27A	0.9700
C11—C12	1.517 (3)	C27—H27B	0.9700
C11—H11A	0.9700	C28—C29	1.504 (3)
C11—H11B	0.9700	C28—H28A	0.9700
C12—C13	1.513 (3)	C28—H28B	0.9700
C12—H12A	0.9700	C29—C30	1.507 (3)
C12—H12B	0.9700	C29—H29A	0.9700
C13—C14	1.513 (3)	C29—H29B	0.9700
C13—H13A	0.9700	C30—C31	1.487 (3)
C13—H13B	0.9700	C30—H30A	0.9700
C14—C15	1.508 (3)	C30—H30B	0.9700
C14—H14A	0.9700	C31—C32	1.494 (3)
C14—H14B	0.9700	C31—H31A	0.9700
C15—C16	1.506 (3)	C31—H31B	0.9700
C15—H15A	0.9700	C32—H32A	0.9600
C15—H15B	0.9700	C32—H32B	0.9600
C16—H16A	0.9600	C32—H32C	0.9600
C16—H16B	0.9600	N1—O1	1.222 (2)
C16—H16C	0.9600	N1—O2	1.223 (2)
C17—C22	1.373 (3)	N2—O4	1.220 (2)
C17—C18	1.374 (3)	N2—O5	1.225 (2)

C6—C1—C2	121.73 (17)	C17—C18—H18	120.3
C6—C1—N1	119.66 (17)	C19—C18—H18	120.3
C2—C1—N1	118.59 (18)	C18—C19—C20	119.66 (18)
C3—C2—C1	118.74 (18)	C18—C19—H19	120.2
C3—C2—H2	120.6	C20—C19—H19	120.2
C1—C2—H2	120.6	O6—C20—C19	124.99 (17)
C2—C3—C4	120.55 (18)	O6—C20—C21	114.94 (16)
C2—C3—H3	119.7	C19—C20—C21	120.08 (16)
C4—C3—H3	119.7	C22—C21—C20	120.23 (17)
O3—C4—C5	124.92 (17)	C22—C21—H21	119.9
O3—C4—C3	115.19 (16)	C20—C21—H21	119.9
C5—C4—C3	119.89 (17)	C17—C22—C21	118.89 (18)
C6—C5—C4	119.46 (17)	C17—C22—H22	120.6
C6—C5—H5	120.3	C21—C22—H22	120.6
C4—C5—H5	120.3	O6—C23—C24	107.35 (16)
C1—C6—C5	119.62 (17)	O6—C23—H23A	110.2
C1—C6—H6	120.2	C24—C23—H23A	110.2
C5—C6—H6	120.2	O6—C23—H23B	110.2
O3—C7—C8	107.42 (16)	C24—C23—H23B	110.2
O3—C7—H7A	110.2	H23A—C23—H23B	108.5
C8—C7—H7A	110.2	C23—C24—C25	114.59 (17)
O3—C7—H7B	110.2	C23—C24—H24A	108.6
C8—C7—H7B	110.2	C25—C24—H24A	108.6
H7A—C7—H7B	108.5	C23—C24—H24B	108.6
C7—C8—C9	114.15 (17)	C25—C24—H24B	108.6
C7—C8—H8A	108.7	H24A—C24—H24B	107.6
C9—C8—H8A	108.7	C26—C25—C24	113.38 (16)
C7—C8—H8B	108.7	C26—C25—H25A	108.9
C9—C8—H8B	108.7	C24—C25—H25A	108.9
H8A—C8—H8B	107.6	C26—C25—H25B	108.9
C10—C9—C8	113.08 (16)	C24—C25—H25B	108.9
C10—C9—H9A	109.0	H25A—C25—H25B	107.7
C8—C9—H9A	109.0	C27—C26—C25	114.50 (16)
C10—C9—H9B	109.0	C27—C26—H26A	108.6
C8—C9—H9B	109.0	C25—C26—H26A	108.6
H9A—C9—H9B	107.8	C27—C26—H26B	108.6
C9—C10—C11	114.62 (16)	C25—C26—H26B	108.6
C9—C10—H10A	108.6	H26A—C26—H26B	107.6
C11—C10—H10A	108.6	C26—C27—C28	114.52 (17)
C9—C10—H10B	108.6	C26—C27—H27A	108.6
C11—C10—H10B	108.6	C28—C27—H27A	108.6
H10A—C10—H10B	107.6	C26—C27—H27B	108.6
C10—C11—C12	113.45 (17)	C28—C27—H27B	108.6
C10—C11—H11A	108.9	H27A—C27—H27B	107.6
C12—C11—H11A	108.9	C29—C28—C27	115.03 (17)
C10—C11—H11B	108.9	C29—C28—H28A	108.5
C12—C11—H11B	108.9	C27—C28—H28A	108.5
H11A—C11—H11B	107.7	C29—C28—H28B	108.5
C13—C12—C11	114.79 (17)	C27—C28—H28B	108.5
C13—C12—H12A	108.6	H28A—C28—H28B	107.5
C11—C12—H12A	108.6	C28—C29—C30	115.36 (18)
C13—C12—H12B	108.6	C28—C29—H29A	108.4
C11—C12—H12B	108.6	C30—C29—H29A	108.4
H12A—C12—H12B	107.5	C28—C29—H29B	108.4
C12—C13—C14	113.73 (17)	C30—C29—H29B	108.4
C12—C13—H13A	108.8	H29A—C29—H29B	107.5
C14—C13—H13A	108.8	C31—C30—C29	115.8 (2)
C12—C13—H13B	108.8	C31—C30—H30A	108.3
C14—C13—H13B	108.8	C29—C30—H30A	108.3
H13A—C13—H13B	107.7	C31—C30—H30B	108.3
C15—C14—C13	115.11 (18)	C29—C30—H30B	108.3
C15—C14—H14A	108.5	H30A—C30—H30B	107.4
C13—C14—H14A	108.5	C30—C31—C32	115.9 (2)
C15—C14—H14B	108.5	C30—C31—H31A	108.3
C13—C14—H14B	108.5	C32—C31—H31A	108.3
H14A—C14—H14B	107.5	C30—C31—H31B	108.3
C16—C15—C14	114.2 (2)	C32—C31—H31B	108.3
C16—C15—H15A	108.7	H31A—C31—H31B	107.4
C14—C15—H15A	108.7	C31—C32—H32A	109.5
C16—C15—H15B	108.7	C31—C32—H32B	109.5
C14—C15—H15B	108.7	H32A—C32—H32B	109.5
H15A—C15—H15B	107.6	C31—C32—H32C	109.5
C15—C16—H16A	109.5	H32A—C32—H32C	109.5
C15—C16—H16B	109.5	H32B—C32—H32C	109.5
H16A—C16—H16B	109.5	O1—N1—O2	122.39 (18)
C15—C16—H16C	109.5	O1—N1—C1	118.43 (18)
H16A—C16—H16C	109.5	O2—N1—C1	119.15 (18)
H16B—C16—H16C	109.5	O4—N2—O5	122.67 (17)
C22—C17—C18	121.79 (16)	O4—N2—C17	119.36 (18)
C22—C17—N2	119.07 (17)	O5—N2—C17	117.95 (17)
C18—C17—N2	119.10 (17)	C4—O3—C7	118.14 (14)
C17—C18—C19	119.34 (17)	C20—O6—C23	118.71 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.93	2.53	3.378 (3)	152
C7—H7B···O5ⁱⁱ	0.97	2.77	3.263 (3)	112
C18—H18···O4ⁱⁱⁱ	0.93	2.60	3.379 (3)	141
C21—H21···O1^iv	0.93	2.70	3.346 (3)	127
C22—H22···O1^iv	0.93	2.79	3.381 (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.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₅NO₃
M_r	279.37
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	5.642 (3), 16.065 (8), 19.135 (7)
α, β, γ (°)	107.410 (16), 90.610 (16), 99.780 (18)
V (Å³)	1627.4 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.19 × 0.17

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.984, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	15990, 7274, 3970
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.176, 0.97
No. of reflections	7274
No. of parameters	363
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.17

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2ⁱ	0.93	2.53	3.378 (3)	152.2
C7—H7B···O5ⁱⁱ	0.97	2.77	3.263 (3)	112.3
C18—H18···O4ⁱⁱⁱ	0.93	2.60	3.379 (3)	141.2
C21—H21···O1^iv	0.93	2.70	3.346 (3)	126.8
C22—H22···O1^iv	0.93	2.79	3.381 (3)	122.8

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

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
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. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 11| November 2009| Page o2627

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