1,1,3-Trimethyl-3-(4-nitro­phen­yl)indane

Men, J.; Yi, S.-X.; Bo, F.; Chen, H.; Gao, G.-W.

doi:10.1107/S1600536808027633

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2192

doi:10.1107/S1600536808027633

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1,1,3-Trimethyl-3-(4-nitrophenyl)indane

Jian Men,^a Shi-Xu Yi,^a Fang Bo,^a Hua Chen ^a and Guo-Wei Gao ^a ^*

^aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: gaosunday@yahoo.com.cn

(Received 21 July 2008; accepted 28 August 2008; online 25 October 2008)

In the title compound, C₁₈H₁₉NO₂, the five-membered ring of the indane fragment adopts an envelope conformation, with the unsubstituted C atom, acting as the flap atom, deviating by 0.412 (3) Å from the plane through the remaining four atoms. The dihedral angle between the nitrophenyl ring and the indane benzene ring is 72.5 (1)°. The distances from the two O atoms to the plane of the adjacent benzene ring are 0.113 (4) and 0.064 (4) Å.

Related literature

For related literature, see: Bateman & Gordon (1976 ); Bezdek & Hrabak et al. (1979 ); Kumar et al. (1983 ); Men et al. (2008 ); Hanaineh-Abdelnour et al. (1999 ).

Experimental

Crystal data

C₁₈H₁₉NO₂
M_r = 281.34
Monoclinic, P 2₁ /c
a = 11.305 (4) Å
b = 11.422 (2) Å
c = 11.963 (2) Å
β = 102.32 (4)°
V = 1509.1 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 294 (2) K
0.48 × 0.42 × 0.40 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3836 measured reflections
2808 independent reflections
1569 reflections with I > 2σ(I)
R_int = 0.005
3 standard reflections every 200 reflections intensity decay: 0.3%

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.148
S = 1.02
2808 reflections
197 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: DIFRAC (Gabe & White, 1993 ); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027633/kj2096sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027633/kj2096Isup2.hkl

checkCIF report

Comment top

Maleimide and its substituted derivatives are well known monomers that have many applications in industry. It may be used to prepare heat resistant polymers or copolymers (Kumar et al., 1983; Bezdek & Hrabak et al., 1979). Excellent thermal properties of the maleimide polymers and copolymers have also attracted much attention (Hanaineh-Abdelnour et al., 1999). The title compound is an important intermediate for synthesis of maleimide and its substituted derivatives. (Bateman & Gordon, 1976). Phenylindane amines is prepared by a process comprising acid-catalyzed dimerization of α-methylstyrene and subsequent nitration and reduction of the 1,1,3-trimethyl-3-phenyl-2,3-dihydro-1H-indene (Bateman & Gordon, 1976).

In the molecule of the title compound (Fig.1), the bond lengths and angles of the phenylidane moiety are comparable with those observed in 1,1,3,-trimethyl-3-phenyl-2,3-dihydro-1H-indene (Men et al., 2008). Ring A (C1—C6) and B (C13—C18) are planar and have a dihedral angle of 72.5 (1)°. The B ring forms a dihedral angle of 27.1 (3)° with the plane defined by the indane Csp3 atoms C7, C9 and C10. The torsion angles O1—N1—C3—C2 and O2—N1—C3—C4 are -174.3 (2)° and -176.5 (2)°, respectively. The distances of the O atoms to the plane through the adjacent benzene ring are 0.113 (4) Å and 0.064 (4) Å, respectively. The five-membered ring of the indane fragment adopts an envelop conformation, with the unsubstituted C atom acting as the flag atom, deviating 0.412 (3) Å from the plane through the remaining four atoms.

Related literature top

For related literature, see: Bateman & Gordon (1976); Bezdek & Hrabak et al. (1979); Kumar et al. (1983); Men et al. (2008); Hanaineh-Abdelnour et al. (1999).

Experimental top

To a three-necked, 250 ml flask equipped with a mechanical stirrer, 23.6 g (0.1 mol) 1,1,3-trimethyl-3-phenylindane, dissolved in 75 ml chloroform, was added. The flask was placed in an ice bath at 273 K. A previously mixed acidic solution containing 39.6 ml H₂SO₄ and 13.2 ml HNO₃ was added dropwise to the phenylidane solution over 4 h at 273 K. The chloroform phase was isolated and washed with an aqueous bicarbonate solution and then with distilled water until neutral. The chloroform was removed with a rotovaporator, thereby yielding a viscous yellow liquid, which was recrystallized from methanol, afforded a light yellow powder (22.0 g, yield 78%, m.p.452–455 K). Single crystals suitable for X-ray diffraction were obtained at room temperature by slow evaporation of ethyl acetate over a period of several days.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level.

1,1,3-Trimethyl-3-(4-nitrophenyl)indane top

Crystal data top

C₁₈H₁₉NO₂	F(000) = 600
M_r = 281.34	D_x = 1.238 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.305 (4) Å	Cell parameters from 25 reflections
b = 11.422 (2) Å	θ = 4.6–7.5°
c = 11.963 (2) Å	µ = 0.08 mm⁻¹
β = 102.32 (4)°	T = 294 K
V = 1509.1 (7) Å³	Block, colourless
Z = 4	0.48 × 0.42 × 0.40 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.005
Radiation source: fine-focus sealed tube	θ_max = 25.6°, θ_min = 1.8°
Graphite monochromator	h = −13→13
ω/2θ scans	k = 0→13
3836 measured reflections	l = −9→14
2808 independent reflections	3 standard reflections every 200 reflections
1569 reflections with I > 2σ(I)	intensity decay: 0.3%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H-atom parameters constrained
wR(F²) = 0.148	w = 1/[σ²(F_o²) + (0.0825P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2808 reflections	Δρ_max = 0.20 e Å⁻³
197 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.017 (3)

Crystal data top

C₁₈H₁₉NO₂	V = 1509.1 (7) Å³
M_r = 281.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.305 (4) Å	µ = 0.08 mm⁻¹
b = 11.422 (2) Å	T = 294 K
c = 11.963 (2) Å	0.48 × 0.42 × 0.40 mm
β = 102.32 (4)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.005
3836 measured reflections	3 standard reflections every 200 reflections
2808 independent reflections	intensity decay: 0.3%
1569 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
2808 reflections	Δρ_min = −0.18 e Å⁻³
197 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
O1	0.3433 (2)	−0.30042 (15)	0.44243 (16)	0.0958 (7)
O2	0.3595 (2)	−0.17051 (16)	0.31987 (16)	0.0899 (7)
N1	0.34612 (19)	−0.19883 (17)	0.41338 (17)	0.0587 (6)
C1	0.3077 (2)	0.08995 (18)	0.53719 (17)	0.0510 (6)
H1	0.3021	0.1679	0.5142	0.067 (3)*
C2	0.3234 (2)	0.00613 (19)	0.45991 (18)	0.0525 (6)
H2	0.3287	0.0263	0.3858	0.067 (3)*
C3	0.3312 (2)	−0.10856 (17)	0.49490 (17)	0.0454 (5)
C4	0.3226 (2)	−0.13981 (18)	0.60329 (18)	0.0523 (6)
H4	0.3265	−0.2181	0.6251	0.067 (3)*
C5	0.3082 (2)	−0.05412 (19)	0.67899 (17)	0.0521 (6)
H5	0.3038	−0.0750	0.7531	0.067 (3)*
C6	0.29992 (18)	0.06319 (18)	0.64821 (16)	0.0412 (5)
C7	0.2858 (2)	0.15488 (17)	0.73769 (16)	0.0447 (5)
C8	0.3994 (2)	0.1497 (2)	0.83509 (18)	0.0616 (7)
H8A	0.4704	0.1586	0.8039	0.088 (3)*
H8B	0.4022	0.0756	0.8735	0.088 (3)*
H8C	0.3963	0.2117	0.8886	0.088 (3)*
C9	0.1683 (2)	0.13740 (19)	0.78272 (18)	0.0544 (6)
H9A	0.1440	0.0558	0.7758	0.068 (5)*
H9B	0.1819	0.1594	0.8628	0.068 (5)*
C10	0.0684 (2)	0.21467 (19)	0.71127 (19)	0.0546 (6)
C11	−0.0054 (3)	0.1487 (2)	0.6080 (2)	0.0786 (8)
H11A	−0.0597	0.2022	0.5606	0.088 (3)*
H11B	−0.0513	0.0877	0.6342	0.088 (3)*
H11C	0.0483	0.1151	0.5646	0.088 (3)*
C12	−0.0166 (3)	0.2629 (3)	0.7825 (3)	0.0865 (9)
H12A	0.0289	0.3071	0.8455	0.088 (3)*
H12B	−0.0570	0.1992	0.8113	0.088 (3)*
H12C	−0.0756	0.3127	0.7359	0.088 (3)*
C13	0.1449 (2)	0.30897 (18)	0.67178 (18)	0.0479 (6)
C14	0.1073 (3)	0.4174 (2)	0.6255 (2)	0.0638 (7)
H14	0.0267	0.4399	0.6150	0.067 (3)*
C15	0.1915 (3)	0.4909 (2)	0.5954 (2)	0.0656 (7)
H15	0.1672	0.5637	0.5640	0.067 (3)*
C16	0.3109 (3)	0.4589 (2)	0.6106 (2)	0.0629 (7)
H16	0.3663	0.5101	0.5896	0.067 (3)*
C17	0.3492 (2)	0.3515 (2)	0.65694 (19)	0.0539 (6)
H17	0.4302	0.3298	0.6680	0.067 (3)*
C18	0.2645 (2)	0.27631 (17)	0.68677 (16)	0.0437 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.170 (2)	0.0401 (10)	0.0774 (12)	0.0122 (11)	0.0259 (13)	−0.0062 (9)
O2	0.152 (2)	0.0637 (11)	0.0666 (12)	0.0012 (12)	0.0525 (12)	−0.0106 (9)
N1	0.0753 (15)	0.0474 (12)	0.0535 (12)	0.0026 (10)	0.0136 (10)	−0.0071 (9)
C1	0.0736 (18)	0.0365 (11)	0.0463 (11)	0.0024 (11)	0.0204 (11)	0.0039 (9)
C2	0.0739 (17)	0.0448 (13)	0.0426 (11)	−0.0010 (11)	0.0208 (11)	0.0024 (10)
C3	0.0503 (15)	0.0411 (11)	0.0457 (11)	0.0029 (10)	0.0124 (10)	−0.0051 (9)
C4	0.0687 (17)	0.0375 (12)	0.0505 (13)	0.0069 (11)	0.0124 (11)	0.0045 (9)
C5	0.0695 (17)	0.0468 (13)	0.0414 (11)	0.0073 (11)	0.0152 (11)	0.0075 (9)
C6	0.0439 (13)	0.0387 (11)	0.0424 (11)	0.0003 (10)	0.0126 (9)	0.0014 (9)
C7	0.0515 (14)	0.0420 (11)	0.0419 (11)	0.0028 (10)	0.0131 (10)	−0.0008 (9)
C8	0.0662 (17)	0.0681 (16)	0.0482 (12)	0.0069 (13)	0.0069 (11)	−0.0068 (11)
C9	0.0644 (17)	0.0517 (14)	0.0530 (12)	0.0029 (12)	0.0258 (11)	0.0020 (10)
C10	0.0490 (15)	0.0538 (14)	0.0648 (14)	−0.0004 (11)	0.0208 (12)	0.0004 (11)
C11	0.0667 (19)	0.0772 (19)	0.0885 (19)	−0.0178 (16)	0.0091 (15)	0.0037 (15)
C12	0.080 (2)	0.081 (2)	0.113 (2)	0.0119 (17)	0.0548 (19)	0.0061 (17)
C13	0.0481 (15)	0.0444 (12)	0.0532 (12)	0.0030 (11)	0.0152 (10)	−0.0057 (10)
C14	0.0608 (17)	0.0524 (15)	0.0776 (16)	0.0115 (13)	0.0135 (13)	0.0005 (12)
C15	0.083 (2)	0.0401 (13)	0.0751 (16)	0.0022 (14)	0.0209 (15)	0.0023 (11)
C16	0.082 (2)	0.0423 (14)	0.0683 (15)	−0.0165 (13)	0.0241 (14)	−0.0082 (11)
C17	0.0547 (16)	0.0492 (13)	0.0595 (13)	−0.0078 (12)	0.0160 (11)	−0.0112 (11)
C18	0.0497 (15)	0.0397 (12)	0.0439 (11)	−0.0010 (10)	0.0147 (10)	−0.0082 (9)

Geometric parameters (Å, º) top

O1—N1	1.214 (2)	C9—H9A	0.9700
O2—N1	1.205 (2)	C9—H9B	0.9700
N1—C3	1.454 (3)	C10—C12	1.518 (3)
C1—C2	1.368 (3)	C10—C13	1.518 (3)
C1—C6	1.384 (3)	C10—C11	1.533 (3)
C1—H1	0.9300	C11—H11A	0.9600
C2—C3	1.372 (3)	C11—H11B	0.9600
C2—H2	0.9300	C11—H11C	0.9600
C3—C4	1.368 (3)	C12—H12A	0.9600
C4—C5	1.366 (3)	C12—H12B	0.9600
C4—H4	0.9300	C12—H12C	0.9600
C5—C6	1.387 (3)	C13—C18	1.377 (3)
C5—H5	0.9300	C13—C14	1.385 (3)
C6—C7	1.530 (3)	C14—C15	1.374 (4)
C7—C18	1.513 (3)	C14—H14	0.9300
C7—C8	1.540 (3)	C15—C16	1.372 (3)
C7—C9	1.550 (3)	C15—H15	0.9300
C8—H8A	0.9600	C16—C17	1.377 (3)
C8—H8B	0.9600	C16—H16	0.9300
C8—H8C	0.9600	C17—C18	1.389 (3)
C9—C10	1.540 (3)	C17—H17	0.9300

O2—N1—O1	122.6 (2)	H9A—C9—H9B	108.4
O2—N1—C3	119.22 (19)	C12—C10—C13	112.8 (2)
O1—N1—C3	118.2 (2)	C12—C10—C11	109.2 (2)
C2—C1—C6	122.54 (19)	C13—C10—C11	110.26 (19)
C2—C1—H1	118.7	C12—C10—C9	111.9 (2)
C6—C1—H1	118.7	C13—C10—C9	100.42 (18)
C1—C2—C3	118.08 (19)	C11—C10—C9	112.0 (2)
C1—C2—H2	121.0	C10—C11—H11A	109.5
C3—C2—H2	121.0	C10—C11—H11B	109.5
C4—C3—C2	121.69 (19)	H11A—C11—H11B	109.5
C4—C3—N1	119.52 (19)	C10—C11—H11C	109.5
C2—C3—N1	118.78 (19)	H11A—C11—H11C	109.5
C5—C4—C3	118.9 (2)	H11B—C11—H11C	109.5
C5—C4—H4	120.5	C10—C12—H12A	109.5
C3—C4—H4	120.5	C10—C12—H12B	109.5
C4—C5—C6	121.78 (19)	H12A—C12—H12B	109.5
C4—C5—H5	119.1	C10—C12—H12C	109.5
C6—C5—H5	119.1	H12A—C12—H12C	109.5
C1—C6—C5	116.97 (18)	H12B—C12—H12C	109.5
C1—C6—C7	123.90 (18)	C18—C13—C14	120.2 (2)
C5—C6—C7	119.12 (17)	C18—C13—C10	112.06 (18)
C18—C7—C6	112.16 (15)	C14—C13—C10	127.8 (2)
C18—C7—C8	112.04 (18)	C15—C14—C13	118.7 (3)
C6—C7—C8	107.99 (17)	C15—C14—H14	120.6
C18—C7—C9	100.55 (17)	C13—C14—H14	120.6
C6—C7—C9	112.34 (17)	C16—C15—C14	121.3 (2)
C8—C7—C9	111.73 (18)	C16—C15—H15	119.4
C7—C8—H8A	109.5	C14—C15—H15	119.4
C7—C8—H8B	109.5	C15—C16—C17	120.4 (2)
H8A—C8—H8B	109.5	C15—C16—H16	119.8
C7—C8—H8C	109.5	C17—C16—H16	119.8
H8A—C8—H8C	109.5	C16—C17—C18	118.7 (2)
H8B—C8—H8C	109.5	C16—C17—H17	120.7
C10—C9—C7	108.33 (17)	C18—C17—H17	120.7
C10—C9—H9A	110.0	C13—C18—C17	120.7 (2)
C7—C9—H9A	110.0	C13—C18—C7	111.63 (19)
C10—C9—H9B	110.0	C17—C18—C7	127.7 (2)
C7—C9—H9B	110.0

C6—C1—C2—C3	0.2 (4)	C7—C9—C10—C11	91.7 (2)
C1—C2—C3—C4	0.5 (4)	C12—C10—C13—C18	134.8 (2)
C1—C2—C3—N1	179.2 (2)	C11—C10—C13—C18	−102.8 (2)
O2—N1—C3—C4	−176.5 (2)	C9—C10—C13—C18	15.5 (2)
O1—N1—C3—C4	4.4 (3)	C12—C10—C13—C14	−45.1 (3)
O2—N1—C3—C2	4.9 (3)	C11—C10—C13—C14	77.3 (3)
O1—N1—C3—C2	−174.3 (2)	C9—C10—C13—C14	−164.4 (2)
C2—C3—C4—C5	−1.2 (4)	C18—C13—C14—C15	−0.1 (3)
N1—C3—C4—C5	−179.8 (2)	C10—C13—C14—C15	179.7 (2)
C3—C4—C5—C6	1.2 (3)	C13—C14—C15—C16	−0.2 (4)
C2—C1—C6—C5	−0.3 (3)	C14—C15—C16—C17	0.0 (4)
C2—C1—C6—C7	178.3 (2)	C15—C16—C17—C18	0.5 (3)
C4—C5—C6—C1	−0.4 (3)	C14—C13—C18—C17	0.6 (3)
C4—C5—C6—C7	−179.1 (2)	C10—C13—C18—C17	−179.25 (18)
C1—C6—C7—C18	7.7 (3)	C14—C13—C18—C7	−179.66 (18)
C5—C6—C7—C18	−173.75 (19)	C10—C13—C18—C7	0.4 (2)
C1—C6—C7—C8	−116.2 (2)	C16—C17—C18—C13	−0.8 (3)
C5—C6—C7—C8	62.3 (3)	C16—C17—C18—C7	179.52 (19)
C1—C6—C7—C9	120.1 (2)	C6—C7—C18—C13	103.5 (2)
C5—C6—C7—C9	−61.4 (3)	C8—C7—C18—C13	−134.8 (2)
C18—C7—C9—C10	25.7 (2)	C9—C7—C18—C13	−16.0 (2)
C6—C7—C9—C10	−93.8 (2)	C6—C7—C18—C17	−76.8 (3)
C8—C7—C9—C10	144.68 (18)	C8—C7—C18—C17	44.8 (3)
C7—C9—C10—C12	−145.3 (2)	C9—C7—C18—C17	163.6 (2)
C7—C9—C10—C13	−25.3 (2)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₉NO₂
M_r	281.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	11.305 (4), 11.422 (2), 11.963 (2)
β (°)	102.32 (4)
V (Å³)	1509.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.48 × 0.42 × 0.40

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3836, 2808, 1569
R_int	0.005
(sin θ/λ)_max (Å⁻¹)	0.607

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.148, 1.02
No. of reflections	2808
No. of parameters	197
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Acknowledgements

The authors are grateful to the National Undergraduates' Innovative Experiment Project of China for financial support and thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

Bateman, J. & Gordon, D. A. (1976). US Patent 3 983 092. Google Scholar
Bezdek, M. & Hrabak, F. J. (1979). Polym. Sci. Polym. Chem. Ed. 17, 2857. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384–387. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gabe, E. J. & White, P. S. (1993). American Crystallographic Association Pittsburgh Meeting, Abstract PA104. Google Scholar
Hanaineh-Abdelnour, L., Bayyuk, S. & Theodorie, R. (1999). Tetrahedron, 50, 11859–11870. Web of Science CrossRef Google Scholar
Kumar, D., Fohlen, G. M. & Parker, J. A. (1983). Macromol. Chem. 16, 1250–1257. CAS Google Scholar
Men, J., Yang, M.-J., Jiang, Y., Chen, H. & Gao, G.-W. (2008). Acta Cryst. E64, o847. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar