3,9-Dimethyl-3,9-bis­(4-nitro­phen­yl)-2,4,8,10-tetra­oxaspiro­[5.5]undeca­ne

Sun, X.; Yu, B.; Zhang, X.; Chao, X.; Chen, Q.

doi:10.1107/S1600536811015017

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1319

doi:10.1107/S1600536811015017

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3,9-Dimethyl-3,9-bis(4-nitrophenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane

Xiaoqiang Sun,^a Bin Yu,^b Xiuqin Zhang,^b ^* Xuqiang Chao ^b and Qiang Chen ^b

^aKey Laboratory of Fine Petrochemical Engineering, Changzhou University, Changzhou 213164, People's Republic of China, and ^bHigh Technology Research Institute of Nanjing University, Changzhou 213162, People's Republic of China
^*Correspondence e-mail: yu_bin235@hotmail.com

(Received 14 March 2011; accepted 21 April 2011; online 7 May 2011)

In the title compound, C₂₁H₂₂N₂O₈, both of the nonplanar six-membered heterocycles adopt chair conformations. The dihedral angle between the terminal benzene rings is 58.22 (11)°. Weak intermolecular C—H⋯O interactions are observed in the crystal structure.

Related literature

For general background to spiranes, see: Cismaş et al. (2005 ); Mihiş et al. (2008 ); Sun et al. (2010 ).

Experimental

Crystal data

C₂₁H₂₂N₂O₈
M_r = 430.41
Triclinic, $[P \overline 1]$
a = 7.4215 (12) Å
b = 11.8790 (18) Å
c = 13.522 (3) Å
α = 115.280 (4)°
β = 94.426 (4)°
γ = 103.444 (3)°
V = 1027.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 295 K
0.21 × 0.21 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.976, T_max = 0.986
5588 measured reflections
3563 independent reflections
2980 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.187
S = 1.07
3563 reflections
282 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O2ⁱ	0.97	2.56	3.515 (3)	168
C10—H10B⋯O1ⁱ	0.97	2.59	3.533 (3)	164
C17—H17⋯O4ⁱⁱ	0.93	2.45	3.337 (3)	160
C20—H20⋯O7ⁱⁱⁱ	0.93	2.37	3.242 (3)	155
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x+1, y, z; (iii) x-1, y, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015017/is2689sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811015017/is2689Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811015017/is2689Isup3.cml

checkCIF report

Comment top

Owing to the characteristic axial and helical chirality, the stereochemistry of spiranes with six-membered rings has been extensively studied (Cismaş et al., 2005). In the past three decades, most of these investigations were carried out with spiranes containing 1,3-dioxane units (Mihiş et al., 2008; Sun et al., 2010). We herein present the structure of 3,9-dimethyl-3,9-di(4-nitrophenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane (Fig. 1).

In the title compound, the two non-planar six-membered heterocycle adopt chair conformations. The dihedral angle between the nitrobenzene rings is 58.22 (11)°. In the crystal structure, weak intermolecular C—H···O interactions contribute to the crystal packing (Table 1).

Related literature top

For general background to spiranes, see: Cismaş et al. (2005); Mihiş et al. (2008); Sun et al. (2010).

Experimental top

To a solution of p-nitroacetophen (2.06 g, 12.5 mmol) and pentaerythritol (0.68 g, 5 mmol) in toluene(30 ml), p-toluenesulfonic acid (0.05 g, 0.3 mmol) as catalyst was added, respectively. Then, the mixtures were refluxed for 6 h to complete the reaction. After reaction, the mixtures were allowed to cool to the room temperature, chloroform (30 ml) was added to dissolve the product, the remain residue was purified by recrystallization using ethanol to provide the title compound as a white solid (85% yield, m.p. 516–517 K). Single crystals suitable for X-ray diffraction were obtained by evaporation of an ethanol and chloroform mixed solution.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

3,9-Dimethyl-3,9-bis(4-nitrophenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane top

Crystal data top

C₂₁H₂₂N₂O₈	Z = 2
M_r = 430.41	F(000) = 452
Triclinic, P1	D_x = 1.392 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4215 (12) Å	Cell parameters from 3502 reflections
b = 11.8790 (18) Å	θ = 2.9–30.2°
c = 13.522 (3) Å	µ = 0.11 mm⁻¹
α = 115.280 (4)°	T = 295 K
β = 94.426 (4)°	Block, colorless
γ = 103.444 (3)°	0.21 × 0.21 × 0.16 mm
V = 1027.0 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	3563 independent reflections
Radiation source: fine-focus sealed tube	2980 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −8→8
T_min = 0.976, T_max = 0.986	k = −14→14
5588 measured reflections	l = −16→11

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.187	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.135P)² + 0.1621P] where P = (F_o² + 2F_c²)/3
3563 reflections	(Δ/σ)_max < 0.001
282 parameters	Δρ_max = 0.37 e Å⁻³
12 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₁H₂₂N₂O₈	γ = 103.444 (3)°
M_r = 430.41	V = 1027.0 (3) Å³
Triclinic, P1	Z = 2
a = 7.4215 (12) Å	Mo Kα radiation
b = 11.8790 (18) Å	µ = 0.11 mm⁻¹
c = 13.522 (3) Å	T = 295 K
α = 115.280 (4)°	0.21 × 0.21 × 0.16 mm
β = 94.426 (4)°

Data collection top

Bruker APEXII CCD diffractometer	3563 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2980 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.986	R_int = 0.022
5588 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	12 restraints
wR(F²) = 0.187	H-atom parameters constrained
S = 1.07	Δρ_max = 0.37 e Å⁻³
3563 reflections	Δρ_min = −0.26 e Å⁻³
282 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
N1	1.2247 (3)	0.6344 (2)	0.63022 (16)	0.0321 (5)
N2	0.1620 (3)	0.14798 (18)	−0.42929 (16)	0.0254 (5)
O1	1.2782 (3)	0.5766 (2)	0.67765 (15)	0.0451 (5)
O2	1.1755 (3)	0.73336 (19)	0.67867 (14)	0.0424 (5)
O3	0.2195 (3)	0.18113 (19)	−0.49758 (15)	0.0398 (5)
O4	−0.0012 (2)	0.13861 (17)	−0.41184 (15)	0.0346 (4)
O5	1.2135 (2)	0.31399 (14)	0.10612 (12)	0.0205 (4)
O6	1.1156 (2)	0.48954 (14)	0.11022 (12)	0.0209 (4)
O7	0.86957 (19)	0.10427 (13)	−0.16096 (12)	0.0192 (4)
O8	0.6406 (2)	0.06651 (14)	−0.06059 (12)	0.0238 (4)
C1	1.2214 (3)	0.5840 (2)	0.51053 (18)	0.0242 (5)
C2	1.2715 (3)	0.4717 (2)	0.45462 (19)	0.0254 (5)
H2A	1.3038	0.4270	0.4920	0.030*
C3	1.2728 (3)	0.4269 (2)	0.34267 (18)	0.0231 (5)
H3A	1.3069	0.3515	0.3041	0.028*
C4	1.2233 (3)	0.4939 (2)	0.28631 (17)	0.0195 (5)
C5	1.1707 (3)	0.6059 (2)	0.34539 (18)	0.0224 (5)
H5	1.1353	0.6501	0.3083	0.027*
C6	1.1703 (3)	0.6524 (2)	0.45800 (18)	0.0244 (5)
H6	1.1366	0.7278	0.4973	0.029*
C7	1.2414 (3)	0.4498 (2)	0.16478 (17)	0.0199 (5)
C8	1.4377 (3)	0.5140 (2)	0.15867 (19)	0.0264 (5)
H8A	1.5284	0.4917	0.1958	0.040*
H8B	1.4615	0.6069	0.1944	0.040*
H8C	1.4484	0.4846	0.0819	0.040*
C9	1.0213 (3)	0.2363 (2)	0.08616 (17)	0.0215 (5)
H9A	0.9863	0.2480	0.1568	0.026*
H9B	1.0111	0.1449	0.0421	0.026*
C10	0.9207 (3)	0.4212 (2)	0.09267 (17)	0.0211 (5)
H10A	0.8431	0.4507	0.0534	0.025*
H10B	0.8844	0.4397	0.1641	0.025*
C11	0.8872 (3)	0.2752 (2)	0.02479 (17)	0.0200 (5)
C12	0.9199 (3)	0.2421 (2)	−0.09323 (17)	0.0187 (5)
H12A	0.8447	0.2786	−0.1264	0.022*
H12B	1.0520	0.2806	−0.0901	0.022*
C13	0.6814 (3)	0.2026 (2)	0.01311 (18)	0.0236 (5)
H13A	0.6576	0.2144	0.0859	0.028*
H13B	0.5984	0.2386	−0.0156	0.028*
C14	0.6799 (3)	0.0390 (2)	−0.16773 (17)	0.0205 (5)
C15	0.6618 (3)	−0.1047 (2)	−0.22524 (19)	0.0282 (5)
H15A	0.7513	−0.1229	−0.1834	0.042*
H15B	0.6865	−0.1289	−0.2991	0.042*
H15C	0.5360	−0.1537	−0.2298	0.042*
C16	0.5415 (3)	0.07090 (19)	−0.23489 (17)	0.0192 (5)
C17	0.5956 (3)	0.0991 (2)	−0.31997 (17)	0.0195 (5)
H17	0.7169	0.1014	−0.3338	0.023*
C18	0.4722 (3)	0.1238 (2)	−0.38398 (17)	0.0204 (5)
H18	0.5097	0.1443	−0.4398	0.024*
C19	0.2916 (3)	0.1176 (2)	−0.36354 (17)	0.0208 (5)
C20	0.2302 (3)	0.0863 (2)	−0.28153 (18)	0.0232 (5)
H20	0.1073	0.0812	−0.2699	0.028*
C21	0.3573 (3)	0.0631 (2)	−0.21751 (18)	0.0236 (5)
H21	0.3192	0.0419	−0.1621	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0187 (10)	0.0450 (13)	0.0191 (10)	−0.0053 (9)	−0.0021 (8)	0.0112 (9)
N2	0.0205 (10)	0.0278 (10)	0.0265 (10)	0.0095 (8)	0.0042 (8)	0.0100 (9)
O1	0.0418 (11)	0.0681 (14)	0.0253 (9)	0.0071 (10)	0.0027 (8)	0.0266 (10)
O2	0.0362 (10)	0.0535 (12)	0.0220 (9)	0.0097 (9)	0.0090 (8)	0.0045 (8)
O3	0.0348 (10)	0.0605 (13)	0.0410 (11)	0.0205 (9)	0.0092 (8)	0.0349 (10)
O4	0.0220 (9)	0.0451 (10)	0.0416 (10)	0.0175 (8)	0.0069 (7)	0.0203 (9)
O5	0.0209 (8)	0.0203 (8)	0.0193 (8)	0.0082 (6)	0.0035 (6)	0.0072 (6)
O6	0.0240 (8)	0.0224 (8)	0.0189 (8)	0.0084 (6)	0.0036 (6)	0.0111 (6)
O7	0.0163 (7)	0.0208 (8)	0.0186 (7)	0.0058 (6)	0.0036 (6)	0.0072 (6)
O8	0.0253 (8)	0.0256 (8)	0.0206 (8)	0.0037 (7)	0.0038 (6)	0.0127 (7)
C1	0.0158 (10)	0.0328 (12)	0.0165 (11)	−0.0022 (9)	0.0014 (8)	0.0097 (10)
C2	0.0214 (11)	0.0306 (12)	0.0237 (11)	0.0004 (9)	−0.0023 (9)	0.0168 (10)
C3	0.0224 (11)	0.0208 (11)	0.0239 (11)	0.0031 (9)	0.0002 (9)	0.0106 (9)
C4	0.0149 (10)	0.0222 (11)	0.0194 (11)	0.0027 (8)	0.0020 (8)	0.0094 (9)
C5	0.0220 (11)	0.0233 (11)	0.0216 (11)	0.0064 (9)	0.0024 (9)	0.0105 (9)
C6	0.0191 (11)	0.0256 (11)	0.0216 (11)	0.0041 (9)	0.0042 (9)	0.0059 (9)
C7	0.0225 (11)	0.0203 (11)	0.0185 (11)	0.0082 (9)	0.0037 (9)	0.0096 (9)
C8	0.0265 (12)	0.0297 (12)	0.0236 (12)	0.0069 (10)	0.0086 (9)	0.0131 (10)
C9	0.0250 (11)	0.0197 (11)	0.0180 (10)	0.0056 (9)	0.0031 (9)	0.0076 (9)
C10	0.0231 (11)	0.0253 (11)	0.0159 (10)	0.0092 (9)	0.0032 (8)	0.0095 (9)
C11	0.0217 (11)	0.0234 (11)	0.0174 (11)	0.0086 (9)	0.0057 (8)	0.0103 (9)
C12	0.0188 (10)	0.0192 (10)	0.0175 (11)	0.0048 (8)	0.0030 (8)	0.0085 (9)
C13	0.0245 (11)	0.0287 (12)	0.0171 (10)	0.0089 (9)	0.0056 (9)	0.0092 (9)
C14	0.0191 (11)	0.0227 (11)	0.0184 (11)	0.0054 (9)	0.0040 (8)	0.0086 (9)
C15	0.0284 (12)	0.0228 (12)	0.0296 (12)	0.0057 (10)	−0.0020 (10)	0.0107 (10)
C16	0.0179 (10)	0.0158 (10)	0.0202 (11)	0.0043 (8)	0.0030 (8)	0.0055 (9)
C17	0.0163 (10)	0.0228 (11)	0.0174 (10)	0.0056 (8)	0.0059 (8)	0.0070 (9)
C18	0.0188 (10)	0.0234 (11)	0.0171 (10)	0.0045 (9)	0.0057 (8)	0.0080 (9)
C19	0.0193 (11)	0.0186 (10)	0.0199 (11)	0.0065 (8)	0.0006 (8)	0.0048 (9)
C20	0.0167 (10)	0.0281 (12)	0.0242 (11)	0.0080 (9)	0.0090 (9)	0.0099 (10)
C21	0.0206 (11)	0.0268 (12)	0.0243 (11)	0.0054 (9)	0.0087 (9)	0.0127 (10)

Geometric parameters (Å, º) top

N1—O1	1.226 (3)	C8—H8C	0.9600
N1—O2	1.234 (3)	C9—C11	1.519 (3)
N1—C1	1.462 (3)	C9—H9A	0.9700
N2—O3	1.218 (2)	C9—H9B	0.9700
N2—O4	1.240 (2)	C10—C11	1.522 (3)
N2—C19	1.466 (3)	C10—H10A	0.9700
O5—C7	1.414 (2)	C10—H10B	0.9700
O5—C9	1.441 (2)	C11—C12	1.526 (3)
O6—C7	1.426 (2)	C11—C13	1.528 (3)
O6—C10	1.430 (2)	C12—H12A	0.9700
O7—C14	1.415 (2)	C12—H12B	0.9700
O7—C12	1.428 (2)	C13—H13A	0.9700
O8—C14	1.413 (2)	C13—H13B	0.9700
O8—C13	1.431 (3)	C14—C15	1.510 (3)
C1—C2	1.379 (3)	C14—C16	1.534 (3)
C1—C6	1.379 (3)	C15—H15A	0.9600
C2—C3	1.375 (3)	C15—H15B	0.9600
C2—H2A	0.9300	C15—H15C	0.9600
C3—C4	1.400 (3)	C16—C17	1.391 (3)
C3—H3A	0.9300	C16—C21	1.393 (3)
C4—C5	1.393 (3)	C17—C18	1.376 (3)
C4—C7	1.525 (3)	C17—H17	0.9300
C5—C6	1.381 (3)	C18—C19	1.381 (3)
C5—H5	0.9300	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.388 (3)
C7—C8	1.506 (3)	C20—C21	1.384 (3)
C8—H8A	0.9600	C20—H20	0.9300
C8—H8B	0.9600	C21—H21	0.9300

O1—N1—O2	123.3 (2)	C11—C10—H10B	109.6
O1—N1—C1	118.2 (2)	H10A—C10—H10B	108.1
O2—N1—C1	118.6 (2)	C9—C11—C10	107.29 (16)
O3—N2—O4	123.52 (19)	C9—C11—C12	111.57 (17)
O3—N2—C19	118.69 (18)	C10—C11—C12	110.46 (16)
O4—N2—C19	117.79 (18)	C9—C11—C13	111.03 (16)
C7—O5—C9	113.97 (15)	C10—C11—C13	109.82 (17)
C7—O6—C10	113.62 (14)	C12—C11—C13	106.70 (17)
C14—O7—C12	113.49 (15)	O7—C12—C11	110.82 (16)
C14—O8—C13	113.91 (15)	O7—C12—H12A	109.5
C2—C1—C6	122.4 (2)	C11—C12—H12A	109.5
C2—C1—N1	119.3 (2)	O7—C12—H12B	109.5
C6—C1—N1	118.3 (2)	C11—C12—H12B	109.5
C3—C2—C1	118.90 (19)	H12A—C12—H12B	108.1
C3—C2—H2A	120.5	O8—C13—C11	110.95 (16)
C1—C2—H2A	120.5	O8—C13—H13A	109.4
C2—C3—C4	120.5 (2)	C11—C13—H13A	109.4
C2—C3—H3A	119.7	O8—C13—H13B	109.4
C4—C3—H3A	119.7	C11—C13—H13B	109.4
C5—C4—C3	118.81 (19)	H13A—C13—H13B	108.0
C5—C4—C7	121.08 (18)	O8—C14—O7	111.31 (16)
C3—C4—C7	119.96 (19)	O8—C14—C15	106.00 (17)
C6—C5—C4	121.19 (19)	O7—C14—C15	106.04 (16)
C6—C5—H5	119.4	O8—C14—C16	111.73 (16)
C4—C5—H5	119.4	O7—C14—C16	111.13 (16)
C1—C6—C5	118.1 (2)	C15—C14—C16	110.34 (17)
C1—C6—H6	120.9	C14—C15—H15A	109.5
C5—C6—H6	120.9	C14—C15—H15B	109.5
O5—C7—O6	111.16 (15)	H15A—C15—H15B	109.5
O5—C7—C8	106.19 (17)	C14—C15—H15C	109.5
O6—C7—C8	106.18 (16)	H15A—C15—H15C	109.5
O5—C7—C4	112.31 (16)	H15B—C15—H15C	109.5
O6—C7—C4	110.65 (16)	C17—C16—C21	119.12 (19)
C8—C7—C4	110.07 (17)	C17—C16—C14	119.69 (18)
C7—C8—H8A	109.5	C21—C16—C14	121.04 (18)
C7—C8—H8B	109.5	C18—C17—C16	120.94 (19)
H8A—C8—H8B	109.5	C18—C17—H17	119.5
C7—C8—H8C	109.5	C16—C17—H17	119.5
H8A—C8—H8C	109.5	C17—C18—C19	118.60 (19)
H8B—C8—H8C	109.5	C17—C18—H18	120.7
O5—C9—C11	110.63 (16)	C19—C18—H18	120.7
O5—C9—H9A	109.5	C18—C19—C20	122.33 (19)
C11—C9—H9A	109.5	C18—C19—N2	118.64 (18)
O5—C9—H9B	109.5	C20—C19—N2	119.01 (18)
C11—C9—H9B	109.5	C21—C20—C19	118.04 (19)
H9A—C9—H9B	108.1	C21—C20—H20	121.0
O6—C10—C11	110.27 (16)	C19—C20—H20	121.0
O6—C10—H10A	109.6	C20—C21—C16	120.92 (19)
C11—C10—H10A	109.6	C20—C21—H21	119.5
O6—C10—H10B	109.6	C16—C21—H21	119.5

O1—N1—C1—C2	2.3 (3)	C14—O7—C12—C11	57.4 (2)
O2—N1—C1—C2	−178.41 (19)	C9—C11—C12—O7	66.9 (2)
O1—N1—C1—C6	−176.8 (2)	C10—C11—C12—O7	−173.87 (15)
O2—N1—C1—C6	2.5 (3)	C13—C11—C12—O7	−54.5 (2)
C6—C1—C2—C3	0.8 (3)	C14—O8—C13—C11	−56.1 (2)
N1—C1—C2—C3	−178.31 (18)	C9—C11—C13—O8	−68.0 (2)
C1—C2—C3—C4	−0.3 (3)	C10—C11—C13—O8	173.56 (15)
C2—C3—C4—C5	−0.7 (3)	C12—C11—C13—O8	53.8 (2)
C2—C3—C4—C7	174.82 (19)	C13—O8—C14—O7	55.3 (2)
C3—C4—C5—C6	1.2 (3)	C13—O8—C14—C15	170.19 (16)
C7—C4—C5—C6	−174.24 (19)	C13—O8—C14—C16	−69.6 (2)
C2—C1—C6—C5	−0.3 (3)	C12—O7—C14—O8	−55.9 (2)
N1—C1—C6—C5	178.84 (18)	C12—O7—C14—C15	−170.77 (15)
C4—C5—C6—C1	−0.8 (3)	C12—O7—C14—C16	69.3 (2)
C9—O5—C7—O6	−54.6 (2)	O8—C14—C16—C17	155.17 (18)
C9—O5—C7—C8	−169.62 (16)	O7—C14—C16—C17	30.2 (2)
C9—O5—C7—C4	70.0 (2)	C15—C14—C16—C17	−87.2 (2)
C10—O6—C7—O5	55.6 (2)	O8—C14—C16—C21	−29.4 (3)
C10—O6—C7—C8	170.66 (16)	O7—C14—C16—C21	−154.43 (19)
C10—O6—C7—C4	−69.9 (2)	C15—C14—C16—C21	88.2 (2)
C5—C4—C7—O5	−154.14 (18)	C21—C16—C17—C18	2.3 (3)
C3—C4—C7—O5	30.5 (3)	C14—C16—C17—C18	177.83 (18)
C5—C4—C7—O6	−29.3 (3)	C16—C17—C18—C19	−1.2 (3)
C3—C4—C7—O6	155.32 (18)	C17—C18—C19—C20	−0.5 (3)
C5—C4—C7—C8	87.8 (2)	C17—C18—C19—N2	178.06 (18)
C3—C4—C7—C8	−87.6 (2)	O3—N2—C19—C18	−2.0 (3)
C7—O5—C9—C11	55.9 (2)	O4—N2—C19—C18	178.18 (19)
C7—O6—C10—C11	−57.5 (2)	O3—N2—C19—C20	176.7 (2)
O5—C9—C11—C10	−54.6 (2)	O4—N2—C19—C20	−3.2 (3)
O5—C9—C11—C12	66.6 (2)	C18—C19—C20—C21	1.1 (3)
O5—C9—C11—C13	−174.56 (16)	N2—C19—C20—C21	−177.47 (18)
O6—C10—C11—C9	55.5 (2)	C19—C20—C21—C16	0.0 (3)
O6—C10—C11—C12	−66.3 (2)	C17—C16—C21—C20	−1.7 (3)
O6—C10—C11—C13	176.29 (15)	C14—C16—C21—C20	−177.16 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2ⁱ	0.97	2.56	3.515 (3)	168
C10—H10B···O1ⁱ	0.97	2.59	3.533 (3)	164
C17—H17···O4ⁱⁱ	0.93	2.45	3.337 (3)	160
C20—H20···O7ⁱⁱⁱ	0.93	2.37	3.242 (3)	155

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂N₂O₈
M_r	430.41
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	7.4215 (12), 11.8790 (18), 13.522 (3)
α, β, γ (°)	115.280 (4), 94.426 (4), 103.444 (3)
V (Å³)	1027.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.21 × 0.21 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.976, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	5588, 3563, 2980
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.187, 1.07
No. of reflections	3563
No. of parameters	282
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2ⁱ	0.9700	2.5600	3.515 (3)	168.00
C10—H10B···O1ⁱ	0.9700	2.5900	3.533 (3)	164.00
C17—H17···O4ⁱⁱ	0.9300	2.4500	3.337 (3)	160.00
C20—H20···O7ⁱⁱⁱ	0.9300	2.3700	3.242 (3)	155.00

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

Acknowledgements

The authors are grateful to Changzhou University and the Natural Science Foundation of China (grant No. 20872051) for financial support.

References

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cismaş, C., Terec, A., Mager, S. & Grosu, I. (2005). Curr. Org. Chem. 9, 1287–1314. Google Scholar
Mihiş, A., Condamine, E., Bogdan, E., Terec, A., Kurtán, T. & Grosu, I. (2008). Molecules, 13, 2848–2858. Web of Science PubMed Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Gemany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sun, X., Yu, S.-L., Li, Z.-Y. & Yang, Y. (2010). J. Mol. Struct. 973, 152–156. Web of Science CSD CrossRef CAS Google Scholar

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Volume 67| Part 6| June 2011| Page o1319

doi:10.1107/S1600536811015017

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,9-Di­methyl-3,9-bis­­(4-nitro­phen­yl)-2,4,8,10-tetra­oxa­spiro­[5.5]undeca­ne

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3,9-Dimethyl-3,9-bis(4-nitrophenyl)-2,4,8,10-tetraoxaspiro[5.5]undecane