Methyl (E)-2-[(2-nitro-phen-oxy)meth-yl]-3-phenyl-acrylate.

The title compound, C(17)H(15)NO(5), adopts an E conformation with respect to the C=C double bond of the phenyl-acrylate unit. The phenyl ring and methyl acrylate group of the phenyl-acrylate unit are disordered over two sets of sites with site-occupancy ratios of 0.705 (5):0.295 (5) and 0.683 (3):0.317 (3), respectively. The mean plane through the benzene ring of the phenyl acrylate makes dihedral angles of 88.4 (8) (major component) and 86.7 (8)° (minor component) with the nitro-phen-oxy ring; the dihedral angle between the two components is 3.64 (6)°. Intra-molecular C-H⋯O interactions stabilise the molecular structure. In the crystal, C-H⋯O inter-actions result in a chain of mol-ecules running along the b axis.

Related literature

For the industrial importance of methyl trans-cinnamates, see: Bhatia et al. (2007 ▶); Huang et al. (2009 ▶); Sharma (2011 ▶). For related structures, see: Anuradha et al. (2011 ▶); Wang et al. (2011 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For background to the synthesis, see: Bakthadoss et al. (2009 ▶).

Experimental

Crystal data

C17H15NO5

M = 313.30

Monoclinic,

a = 24.0511 (10) Å

b = 7.8521 (3) Å

c = 19.7403 (9) Å

β = 121.661 (3)°

V = 3173.1 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.971, T max = 0.981

32853 measured reflections

3695 independent reflections

2356 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.145

S = 1.12

3695 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812021009/pv2539sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021009/pv2539Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021009/pv2539Isup3.cml

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

C17H15NO5	F(000) = 1312
Mr = 313.30	Dx = 1.312 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3695 reflections
a = 24.0511 (10) Å	θ = 2.2–27.7°
b = 7.8521 (3) Å	µ = 0.10 mm−1
c = 19.7403 (9) Å	T = 293 K
β = 121.661 (3)°	Block, colourless
V = 3173.1 (2) Å3	0.30 × 0.20 × 0.20 mm
Z = 8

Bruker SMART APEXII area-detector diffractometer	3695 independent reflections
Radiation source: fine-focus sealed tube	2356 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scans	θmax = 27.7°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −31→31
Tmin = 0.971, Tmax = 0.981	k = −10→10
32853 measured reflections	l = −25→25

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) = 0.145	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0548P)2 + 1.2534P] where P = (Fo2 + 2Fc2)/3
3695 reflections	(Δ/σ)max = 0.008
212 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.04775 (8)	0.71127 (19)	−0.03978 (10)	0.0530 (4)
C2	−0.00796 (9)	0.7393 (2)	−0.11206 (11)	0.0646 (5)
H2	−0.0326	0.6479	−0.1435	0.078*
C3	−0.02733 (9)	0.9032 (2)	−0.13791 (12)	0.0722 (5)
H3	−0.0652	0.9239	−0.1868	0.087*
C4	0.00989 (9)	1.0359 (2)	−0.09087 (11)	0.0684 (5)
H4	−0.0035	1.1470	−0.1080	0.082*
C5	0.06650 (8)	1.0086 (2)	−0.01904 (10)	0.0581 (4)
H5	0.0912	1.1008	0.0115	0.070*
C6	0.08709 (7)	0.84407 (19)	0.00821 (9)	0.0494 (4)
C7	0.18319 (8)	0.9397 (2)	0.12608 (10)	0.0561 (4)
H7A	0.1617	0.9959	0.1501	0.067*
H7B	0.1897	1.0228	0.0945	0.067*
C8	0.24735 (8)	0.8703 (2)	0.18938 (11)	0.0598 (4)
C9	0.26255 (9)	0.8346 (2)	0.26281 (11)	0.0698 (5)
H9	0.3061	0.8069	0.2985	0.084*
O5	0.14319 (5)	0.80287 (13)	0.07619 (7)	0.0586 (3)
N1	0.06558 (8)	0.53526 (19)	−0.01355 (12)	0.0696 (4)
O1	0.08558 (8)	0.49972 (19)	0.05526 (11)	0.1018 (6)
O2	0.05728 (10)	0.43151 (19)	−0.06366 (12)	0.1139 (6)
O3	0.35656 (19)	0.8059 (6)	0.2290 (2)	0.1002 (11)	0.683 (3)
O4	0.28384 (12)	0.8651 (4)	0.1015 (2)	0.0720 (7)	0.683 (3)
C17	0.33209 (17)	0.8375 (5)	0.0840 (2)	0.0942 (9)	0.683 (3)
H17A	0.3619	0.9319	0.1028	0.141*	0.683 (3)
H17B	0.3123	0.8267	0.0274	0.141*	0.683 (3)
H17C	0.3554	0.7348	0.1095	0.141*	0.683 (3)
C16	0.30259 (19)	0.8415 (5)	0.1786 (2)	0.0616 (8)	0.683 (3)
O3'	0.2676 (4)	0.9073 (12)	0.0829 (6)	0.1002 (11)	0.317 (3)
O4'	0.3504 (4)	0.8074 (11)	0.2006 (4)	0.0720 (7)	0.317 (3)
C17'	0.3931 (4)	0.8028 (11)	0.1689 (5)	0.0942 (9)	0.317 (3)
H17D	0.3785	0.7156	0.1291	0.141*	0.317 (3)
H17E	0.4369	0.7786	0.2112	0.141*	0.317 (3)
H17F	0.3919	0.9111	0.1457	0.141*	0.317 (3)
C16'	0.2889 (5)	0.8675 (13)	0.1467 (6)	0.0616 (8)	0.317 (3)
C10	0.21965 (15)	0.8329 (3)	0.29588 (16)	0.0693 (5)	0.705 (5)
C11	0.15778 (8)	0.76028 (14)	0.24978 (8)	0.0740 (6)	0.705 (5)
H11	0.1441	0.7189	0.1992	0.089*	0.705 (5)
C12	0.11639 (8)	0.74947 (14)	0.27897 (8)	0.0868 (8)	0.705 (5)
H12	0.0750	0.7020	0.2478	0.104*	0.705 (5)
C13	0.13684 (8)	0.80956 (14)	0.35480 (8)	0.0957 (11)	0.705 (5)
H13	0.1091	0.8023	0.3743	0.115*	0.705 (5)
C14	0.19868 (8)	0.88046 (14)	0.40143 (8)	0.1047 (12)	0.705 (5)
H14	0.2124	0.9207	0.4522	0.126*	0.705 (5)
C15	0.24007 (8)	0.89128 (14)	0.37224 (8)	0.0906 (8)	0.705 (5)
H15	0.2816	0.9377	0.4038	0.109*	0.705 (5)
C10'	0.22131 (8)	0.82692 (14)	0.29177 (8)	0.0693 (5)	0.295 (5)
C11'	0.15763 (8)	0.76783 (14)	0.25774 (8)	0.0740 (6)	0.295 (5)
H11'	0.1350	0.7290	0.2054	0.089*	0.295 (5)
C12'	0.12776 (8)	0.76678 (14)	0.30186 (8)	0.0868 (8)	0.295 (5)
H12'	0.0851	0.7272	0.2791	0.104*	0.295 (5)
C13'	0.16156 (8)	0.82481 (14)	0.38001 (8)	0.0957 (11)	0.295 (5)
H13'	0.1416	0.8241	0.4095	0.115*	0.295 (5)
C14'	0.22524 (8)	0.88390 (14)	0.41404 (8)	0.1047 (12)	0.295 (5)
H14'	0.2479	0.9227	0.4663	0.126*	0.295 (5)
C15'	0.25511 (8)	0.88495 (14)	0.36992 (8)	0.0906 (8)	0.295 (5)
H15'	0.2977	0.9245	0.3927	0.109*	0.295 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0514 (9)	0.0474 (8)	0.0629 (10)	−0.0054 (7)	0.0317 (8)	−0.0016 (7)
C2	0.0574 (10)	0.0612 (10)	0.0651 (11)	−0.0131 (8)	0.0252 (9)	−0.0118 (8)
C3	0.0590 (11)	0.0702 (12)	0.0622 (11)	−0.0030 (9)	0.0144 (9)	0.0014 (9)
C4	0.0630 (11)	0.0555 (9)	0.0670 (12)	0.0017 (8)	0.0206 (10)	0.0051 (8)
C5	0.0567 (10)	0.0485 (8)	0.0574 (10)	−0.0040 (7)	0.0219 (8)	−0.0024 (7)
C6	0.0476 (9)	0.0510 (8)	0.0501 (9)	−0.0043 (6)	0.0260 (8)	−0.0011 (7)
C7	0.0545 (9)	0.0500 (8)	0.0536 (9)	−0.0059 (7)	0.0213 (8)	−0.0018 (7)
C8	0.0514 (9)	0.0539 (9)	0.0609 (11)	−0.0018 (7)	0.0204 (8)	−0.0026 (8)
C9	0.0615 (11)	0.0590 (10)	0.0628 (12)	0.0052 (8)	0.0146 (9)	0.0041 (8)
O5	0.0540 (7)	0.0487 (6)	0.0561 (7)	−0.0037 (5)	0.0172 (6)	0.0015 (5)
N1	0.0605 (9)	0.0495 (8)	0.0984 (13)	−0.0112 (7)	0.0414 (9)	−0.0019 (8)
O1	0.1010 (12)	0.0756 (10)	0.1010 (12)	−0.0169 (8)	0.0338 (10)	0.0265 (9)
O2	0.1455 (16)	0.0531 (8)	0.1600 (17)	−0.0084 (9)	0.0919 (14)	−0.0197 (10)
O3	0.0626 (15)	0.140 (2)	0.078 (2)	0.0263 (14)	0.0233 (18)	0.008 (2)
O4	0.0476 (14)	0.0938 (16)	0.069 (2)	0.0054 (10)	0.0265 (15)	0.0008 (13)
C17	0.086 (2)	0.120 (3)	0.099 (2)	−0.0060 (19)	0.0632 (18)	−0.003 (2)
C16	0.049 (2)	0.0636 (17)	0.051 (3)	0.0007 (14)	0.012 (2)	0.0024 (17)
O3'	0.0626 (15)	0.140 (2)	0.078 (2)	0.0263 (14)	0.0233 (18)	0.008 (2)
O4'	0.0476 (14)	0.0938 (16)	0.069 (2)	0.0054 (10)	0.0265 (15)	0.0008 (13)
C17'	0.086 (2)	0.120 (3)	0.099 (2)	−0.0060 (19)	0.0632 (18)	−0.003 (2)
C16'	0.049 (2)	0.0636 (17)	0.051 (3)	0.0007 (14)	0.012 (2)	0.0024 (17)
C10	0.0848 (14)	0.0554 (10)	0.0554 (11)	0.0092 (9)	0.0284 (10)	0.0094 (8)
C11	0.0916 (15)	0.0683 (12)	0.0651 (12)	0.0022 (10)	0.0432 (12)	0.0089 (9)
C12	0.106 (2)	0.0881 (16)	0.0731 (18)	0.0032 (14)	0.0516 (17)	0.0131 (14)
C13	0.127 (3)	0.0971 (19)	0.079 (2)	0.009 (2)	0.065 (2)	0.0098 (17)
C14	0.136 (4)	0.106 (2)	0.084 (2)	−0.004 (2)	0.066 (3)	−0.0063 (16)
C15	0.109 (2)	0.0903 (17)	0.0643 (13)	−0.0018 (14)	0.0402 (15)	−0.0044 (12)
C10'	0.0848 (14)	0.0554 (10)	0.0554 (11)	0.0092 (9)	0.0284 (10)	0.0094 (8)
C11'	0.0916 (15)	0.0683 (12)	0.0651 (12)	0.0022 (10)	0.0432 (12)	0.0089 (9)
C12'	0.106 (2)	0.0881 (16)	0.0731 (18)	0.0032 (14)	0.0516 (17)	0.0131 (14)
C13'	0.127 (3)	0.0971 (19)	0.079 (2)	0.009 (2)	0.065 (2)	0.0098 (17)
C14'	0.136 (4)	0.106 (2)	0.084 (2)	−0.004 (2)	0.066 (3)	−0.0063 (16)
C15'	0.109 (2)	0.0903 (17)	0.0643 (13)	−0.0018 (14)	0.0402 (15)	−0.0044 (12)

C1—C2	1.369 (2)	C17—H17C	0.9600
C1—C6	1.392 (2)	O3'—C16'	1.126 (14)
C1—N1	1.459 (2)	O4'—C16'	1.375 (14)
C2—C3	1.372 (3)	O4'—C17'	1.456 (9)
C2—H2	0.9300	C17'—H17D	0.9600
C3—C4	1.370 (2)	C17'—H17E	0.9600
C3—H3	0.9300	C17'—H17F	0.9600
C4—C5	1.372 (2)	C10—C15	1.395 (3)
C4—H4	0.9300	C10—C11	1.395 (4)
C5—C6	1.387 (2)	C11—C12	1.3900
C5—H5	0.9300	C11—H11	0.9300
C6—O5	1.3510 (18)	C12—C13	1.3900
C7—O5	1.4334 (18)	C12—H12	0.9300
C7—C8	1.489 (2)	C13—C14	1.3900
C7—H7A	0.9700	C13—H13	0.9300
C7—H7B	0.9700	C14—C15	1.3900
C8—C9	1.325 (3)	C14—H14	0.9300
C8—C16	1.469 (5)	C15—H15	0.9300
C8—C16'	1.610 (13)	C10'—C11'	1.3900
C9—C10'	1.382 (3)	C10'—C15'	1.3900
C9—C10	1.483 (4)	C11'—C12'	1.3900
C9—H9	0.9300	C11'—H11'	0.9300
N1—O1	1.212 (2)	C12'—C13'	1.3900
N1—O2	1.214 (2)	C12'—H12'	0.9300
O3—C16	1.182 (5)	C13'—C14'	1.3900
O4—C16	1.353 (4)	C13'—H13'	0.9300
O4—C17	1.392 (4)	C14'—C15'	1.3900
C17—H17A	0.9600	C14'—H14'	0.9300
C17—H17B	0.9600	C15'—H15'	0.9300
C2—C1—C6	122.17 (15)	O4'—C17'—H17E	109.5
C2—C1—N1	117.84 (15)	H17D—C17'—H17E	109.5
C6—C1—N1	119.98 (15)	O4'—C17'—H17F	109.5
C1—C2—C3	119.61 (16)	H17D—C17'—H17F	109.5
C1—C2—H2	120.2	H17E—C17'—H17F	109.5
C3—C2—H2	120.2	O3'—C16'—O4'	129.3 (12)
C4—C3—C2	119.18 (17)	O3'—C16'—C8	122.6 (9)
C4—C3—H3	120.4	O4'—C16'—C8	108.1 (7)
C2—C3—H3	120.4	C15—C10—C11	119.3 (3)
C3—C4—C5	121.49 (17)	C15—C10—C9	122.8 (2)
C3—C4—H4	119.3	C11—C10—C9	117.9 (2)
C5—C4—H4	119.3	C12—C11—C10	120.36 (15)
C4—C5—C6	120.32 (15)	C12—C11—H11	119.8
C4—C5—H5	119.8	C10—C11—H11	119.8
C6—C5—H5	119.8	C11—C12—C13	120.0
O5—C6—C5	125.12 (14)	C11—C12—H12	120.0
O5—C6—C1	117.65 (14)	C13—C12—H12	120.0
C5—C6—C1	117.19 (14)	C12—C13—C14	120.0
O5—C7—C8	109.18 (13)	C12—C13—H13	120.0
O5—C7—H7A	109.8	C14—C13—H13	120.0
C8—C7—H7A	109.8	C13—C14—C15	120.0
O5—C7—H7B	109.8	C13—C14—H14	120.0
C8—C7—H7B	109.8	C15—C14—H14	120.0
H7A—C7—H7B	108.3	C14—C15—C10	120.35 (15)
C9—C8—C16	112.0 (2)	C14—C15—H15	119.8
C9—C8—C7	124.38 (17)	C10—C15—H15	119.8
C16—C8—C7	123.5 (2)	C9—C10'—C11'	131.51 (10)
C9—C8—C16'	132.8 (4)	C9—C10'—C15'	108.43 (10)
C7—C8—C16'	102.7 (4)	C11'—C10'—C15'	120.0
C8—C9—C10'	128.02 (17)	C12'—C11'—C10'	120.0
C8—C9—C10	128.86 (19)	C12'—C11'—H11'	120.0
C8—C9—H9	115.6	C10'—C11'—H11'	120.0
C10'—C9—H9	116.4	C11'—C12'—C13'	120.0
C10—C9—H9	115.6	C11'—C12'—H12'	120.0
C6—O5—C7	117.59 (12)	C13'—C12'—H12'	120.0
O1—N1—O2	123.87 (18)	C14'—C13'—C12'	120.0
O1—N1—C1	119.05 (16)	C14'—C13'—H13'	120.0
O2—N1—C1	117.03 (18)	C12'—C13'—H13'	120.0
C16—O4—C17	115.4 (3)	C13'—C14'—C15'	120.0
O3—C16—O4	123.3 (4)	C13'—C14'—H14'	120.0
O3—C16—C8	126.3 (3)	C15'—C14'—H14'	120.0
O4—C16—C8	110.4 (3)	C10'—C15'—C14'	120.0
C16'—O4'—C17'	113.0 (8)	C10'—C15'—H15'	120.0
O4'—C17'—H17D	109.5	C14'—C15'—H15'	120.0
C6—C1—C2—C3	−1.9 (3)	C16'—C8—C16—O4	−9.8 (12)
N1—C1—C2—C3	178.29 (17)	C17'—O4'—C16'—O3'	2.5 (17)
C1—C2—C3—C4	0.4 (3)	C17'—O4'—C16'—C8	−178.7 (6)
C2—C3—C4—C5	0.9 (3)	C9—C8—C16'—O3'	−177.7 (8)
C3—C4—C5—C6	−0.8 (3)	C16—C8—C16'—O3'	176 (2)
C4—C5—C6—O5	177.10 (16)	C7—C8—C16'—O3'	−2.1 (12)
C4—C5—C6—C1	−0.6 (3)	C9—C8—C16'—O4'	3.4 (11)
C2—C1—C6—O5	−175.93 (15)	C16—C8—C16'—O4'	−2.5 (9)
N1—C1—C6—O5	3.9 (2)	C7—C8—C16'—O4'	179.0 (6)
C2—C1—C6—C5	2.0 (2)	C8—C9—C10—C15	−141.3 (2)
N1—C1—C6—C5	−178.22 (15)	C10'—C9—C10—C15	148 (3)
O5—C7—C8—C9	−97.96 (19)	C8—C9—C10—C11	42.5 (3)
O5—C7—C8—C16	85.3 (3)	C10'—C9—C10—C11	−28 (3)
O5—C7—C8—C16'	85.9 (4)	C15—C10—C11—C12	1.3 (3)
C16—C8—C9—C10'	−171.5 (2)	C9—C10—C11—C12	177.64 (13)
C7—C8—C9—C10'	11.4 (3)	C10—C11—C12—C13	−0.67 (14)
C16'—C8—C9—C10'	−173.8 (5)	C11—C12—C13—C14	0.0
C16—C8—C9—C10	−174.4 (2)	C12—C13—C14—C15	0.0
C7—C8—C9—C10	8.5 (3)	C13—C14—C15—C10	0.66 (14)
C16'—C8—C9—C10	−176.7 (5)	C11—C10—C15—C14	−1.3 (3)
C5—C6—O5—C7	3.1 (2)	C9—C10—C15—C14	−177.45 (14)
C1—C6—O5—C7	−179.15 (14)	C8—C9—C10'—C11'	37.6 (2)
C8—C7—O5—C6	−169.94 (14)	C10—C9—C10'—C11'	149 (3)
C2—C1—N1—O1	−137.99 (18)	C8—C9—C10'—C15'	−145.33 (17)
C6—C1—N1—O1	42.2 (2)	C10—C9—C10'—C15'	−34 (3)
C2—C1—N1—O2	39.7 (2)	C9—C10'—C11'—C12'	176.81 (12)
C6—C1—N1—O2	−140.11 (18)	C15'—C10'—C11'—C12'	0.0
C17—O4—C16—O3	2.7 (6)	C10'—C11'—C12'—C13'	0.0
C17—O4—C16—C8	−178.7 (3)	C11'—C12'—C13'—C14'	0.0
C9—C8—C16—O3	−6.5 (5)	C12'—C13'—C14'—C15'	0.0
C7—C8—C16—O3	170.6 (4)	C9—C10'—C15'—C14'	−177.49 (9)
C16'—C8—C16—O3	168.8 (17)	C11'—C10'—C15'—C14'	0.0
C9—C8—C16—O4	174.8 (2)	C13'—C14'—C15'—C10'	0.0
C7—C8—C16—O4	−8.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O3	0.93	2.26	2.683 (5)	107
C11—H11···O5	0.93	2.51	3.2734 (17)	140
C2—H2···O3i	0.93	2.56	3.140 (4)	121
C3—H3···O3i	0.93	2.51	3.114 (5)	123
C4—H4···O2ii	0.93	2.56	3.255 (2)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O3	0.93	2.26	2.683 (5)	107
C11—H11⋯O5	0.93	2.51	3.2734 (17)	140
C2—H2⋯O3i	0.93	2.56	3.140 (4)	121
C3—H3⋯O3i	0.93	2.51	3.114 (5)	123
C4—H4⋯O2ii	0.93	2.56	3.255 (2)	132

Symmetry codes: (i) ; (ii) .