rac-Dimethyl 5-oxo-2-[(2,4,4-trimethyl-pentan-2-yl)amino]-4,5-dihydro-pyrano[3,2-c]chromene-3,4-dicarboxyl-ate.

The title compound, C(24)H(29)NO(7), is asymmetric with a chiral centre located in the pyran ring and crystallizes as a racemate. The coumarin ring system and the fused pyran ring make a dihedral angle of 10.46 (8)°. A short intra-molecular N-H⋯O hydrogen bond between the amino group and the vicinal carbonyl group generates an S(6) ring. Inter-molecular C-H⋯O inter-actions contribute to the stability of the crystal structure.

Related literature

For the biological activity of pyran­ocoumarin compounds, see: Kawaii et al. (2001 ▶); Goel et al. (1997 ▶); Xu et al. (2006 ▶). For a similar compound, see: Inglebert et al. (2011 ▶). For bond-angle distortions, see: Chinnakali et al. (1998 ▶); Kumar et al. (1997 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H29NO7

M = 443.48

Monoclinic,

a = 22.0329 (17) Å

b = 11.8675 (8) Å

c = 18.4861 (14) Å

β = 107.946 (4)°

V = 4598.5 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.35 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.972, T max = 0.981

17657 measured reflections

3384 independent reflections

2623 reflections with I > 2σ(I)

R int = 0.035

θmax = 23.5°

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.130

S = 1.01

3384 reflections

296 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027596/fy2059sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027596/fy2059Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027596/fy2059Isup3.cml

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

C24H29NO7	F(000) = 1888
Mr = 443.48	Dx = 1.281 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3384 reflections
a = 22.0329 (17) Å	θ = 2.1–23.5°
b = 11.8675 (8) Å	µ = 0.09 mm−1
c = 18.4861 (14) Å	T = 293 K
β = 107.946 (4)°	Block, colourless
V = 4598.5 (6) Å3	0.35 × 0.25 × 0.20 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	3384 independent reflections
Radiation source: fine-focus sealed tube	2623 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
ω and φ scan	θmax = 23.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −24→24
Tmin = 0.972, Tmax = 0.981	k = −13→13
17657 measured reflections	l = −20→20

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0745P)2 + 2.5421P] where P = (Fo2 + 2Fc2)/3
3384 reflections	(Δ/σ)max < 0.001
296 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.24 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
C1	0.07781 (10)	0.65241 (18)	0.08539 (12)	0.0434 (5)
C2	0.01923 (11)	0.6706 (2)	0.09593 (14)	0.0580 (6)
H2	−0.0163	0.6291	0.0690	0.070*
C3	0.01469 (13)	0.7514 (3)	0.14700 (16)	0.0707 (8)
H3	−0.0245	0.7649	0.1545	0.085*
C4	0.06739 (12)	0.8128 (2)	0.18737 (15)	0.0666 (7)
H4	0.0634	0.8669	0.2220	0.080*
C5	0.12543 (11)	0.7948 (2)	0.17689 (13)	0.0538 (6)
H5	0.1607	0.8367	0.2042	0.065*
C6	0.13161 (10)	0.71310 (18)	0.12499 (12)	0.0411 (5)
C7	0.18985 (9)	0.68570 (17)	0.10922 (11)	0.0362 (5)
C8	0.19380 (9)	0.60197 (16)	0.06255 (11)	0.0356 (5)
C9	0.13680 (10)	0.54036 (18)	0.02177 (12)	0.0408 (5)
C10	0.25577 (9)	0.56956 (16)	0.05062 (11)	0.0359 (5)
H10	0.2486	0.5539	−0.0034	0.043*
C11	0.30259 (9)	0.66519 (16)	0.07534 (10)	0.0347 (5)
C12	0.29355 (9)	0.74938 (16)	0.12167 (11)	0.0348 (5)
C13	0.28234 (10)	0.46404 (17)	0.09713 (13)	0.0413 (5)
C14	0.31163 (16)	0.2746 (2)	0.09316 (18)	0.0842 (9)
H14A	0.3533	0.2905	0.1276	0.126*
H14B	0.3150	0.2190	0.0569	0.126*
H14C	0.2847	0.2465	0.1212	0.126*
C15	0.36146 (10)	0.66180 (18)	0.05798 (11)	0.0412 (5)
C16	0.42747 (14)	0.5498 (2)	0.0079 (2)	0.0802 (9)
H16A	0.4391	0.6164	−0.0141	0.120*
H16B	0.4244	0.4873	−0.0260	0.120*
H16C	0.4594	0.5341	0.0555	0.120*
C17	0.33589 (10)	0.91740 (17)	0.20939 (12)	0.0419 (5)
C18	0.27751 (13)	0.99465 (19)	0.18546 (14)	0.0598 (7)
H18A	0.2732	1.0257	0.1362	0.090*
H18B	0.2827	1.0546	0.2217	0.090*
H18C	0.2400	0.9521	0.1835	0.090*
C19	0.39446 (13)	0.9891 (2)	0.21481 (15)	0.0643 (7)
H19A	0.4314	0.9415	0.2250	0.096*
H19B	0.4005	1.0429	0.2552	0.096*
H19C	0.3885	1.0282	0.1676	0.096*
C20	0.33782 (10)	0.85921 (18)	0.28459 (11)	0.0442 (5)
H20A	0.3367	0.9190	0.3199	0.053*
H20B	0.2979	0.8186	0.2746	0.053*
C21	0.39048 (12)	0.7775 (2)	0.32812 (13)	0.0598 (7)
C22	0.4003 (2)	0.6793 (3)	0.28107 (18)	0.1349 (19)
H22A	0.3602	0.6425	0.2579	0.202*
H22B	0.4296	0.6268	0.3132	0.202*
H22C	0.4173	0.7060	0.2422	0.202*
C23	0.45323 (14)	0.8378 (3)	0.36641 (19)	0.1006 (11)
H23A	0.4809	0.7889	0.4035	0.151*
H23B	0.4451	0.9049	0.3909	0.151*
H23C	0.4733	0.8577	0.3289	0.151*
C24	0.3680 (2)	0.7316 (3)	0.39292 (19)	0.1155 (13)
H24A	0.3293	0.6894	0.3721	0.173*
H24B	0.3602	0.7932	0.4225	0.173*
H24C	0.4003	0.6834	0.4247	0.173*
N1	0.33318 (8)	0.83453 (14)	0.14823 (9)	0.0427 (4)
H1	0.3621	0.8432	0.1264	0.051*
O1	0.08075 (6)	0.56951 (12)	0.03460 (8)	0.0464 (4)
O2	0.13476 (7)	0.46490 (13)	−0.02235 (9)	0.0550 (4)
O3	0.24034 (6)	0.75349 (12)	0.14530 (8)	0.0416 (4)
O4	0.29947 (10)	0.46127 (14)	0.16463 (10)	0.0717 (6)
O5	0.28442 (8)	0.37646 (12)	0.05382 (9)	0.0620 (5)
O6	0.40352 (7)	0.73256 (13)	0.07379 (9)	0.0530 (4)
O7	0.36707 (8)	0.56715 (13)	0.02049 (10)	0.0614 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0370 (13)	0.0505 (13)	0.0409 (12)	−0.0018 (10)	0.0096 (9)	0.0054 (11)
C2	0.0359 (13)	0.0777 (17)	0.0587 (15)	−0.0055 (12)	0.0120 (11)	0.0052 (14)
C3	0.0436 (15)	0.099 (2)	0.0752 (18)	0.0093 (15)	0.0270 (13)	−0.0021 (17)
C4	0.0557 (17)	0.0817 (18)	0.0679 (17)	0.0057 (14)	0.0272 (14)	−0.0140 (14)
C5	0.0436 (14)	0.0648 (15)	0.0543 (14)	−0.0019 (12)	0.0168 (11)	−0.0102 (12)
C6	0.0349 (12)	0.0460 (12)	0.0417 (12)	0.0010 (10)	0.0108 (9)	0.0014 (10)
C7	0.0315 (11)	0.0392 (11)	0.0345 (11)	−0.0039 (9)	0.0052 (8)	0.0002 (9)
C8	0.0345 (12)	0.0339 (11)	0.0355 (11)	−0.0043 (9)	0.0067 (9)	0.0021 (9)
C9	0.0393 (13)	0.0406 (12)	0.0399 (12)	−0.0048 (10)	0.0086 (9)	0.0051 (10)
C10	0.0366 (11)	0.0358 (11)	0.0345 (11)	−0.0039 (9)	0.0098 (9)	−0.0032 (9)
C11	0.0337 (11)	0.0332 (11)	0.0358 (10)	−0.0038 (9)	0.0087 (9)	−0.0006 (9)
C12	0.0318 (11)	0.0360 (11)	0.0346 (11)	−0.0026 (9)	0.0075 (9)	0.0006 (9)
C13	0.0381 (12)	0.0374 (12)	0.0474 (14)	−0.0037 (9)	0.0117 (10)	−0.0030 (10)
C14	0.096 (2)	0.0413 (14)	0.102 (2)	0.0201 (15)	0.0102 (18)	−0.0025 (14)
C15	0.0416 (13)	0.0395 (12)	0.0424 (12)	−0.0045 (11)	0.0128 (10)	−0.0022 (10)
C16	0.0652 (18)	0.0710 (18)	0.123 (3)	−0.0001 (15)	0.0564 (18)	−0.0253 (17)
C17	0.0446 (13)	0.0368 (11)	0.0428 (12)	−0.0036 (10)	0.0111 (10)	−0.0089 (9)
C18	0.0705 (17)	0.0421 (13)	0.0578 (14)	0.0103 (12)	0.0064 (12)	−0.0015 (11)
C19	0.0749 (18)	0.0552 (15)	0.0645 (15)	−0.0293 (13)	0.0243 (14)	−0.0208 (12)
C20	0.0428 (13)	0.0444 (12)	0.0423 (12)	0.0008 (10)	0.0086 (10)	−0.0074 (10)
C21	0.0651 (17)	0.0523 (14)	0.0490 (14)	0.0163 (12)	−0.0016 (12)	−0.0029 (11)
C22	0.192 (4)	0.088 (2)	0.079 (2)	0.089 (3)	−0.025 (2)	−0.0216 (19)
C23	0.060 (2)	0.117 (3)	0.101 (2)	0.0290 (18)	−0.0102 (17)	−0.010 (2)
C24	0.153 (4)	0.099 (3)	0.079 (2)	0.022 (2)	0.014 (2)	0.038 (2)
N1	0.0449 (11)	0.0427 (10)	0.0434 (10)	−0.0124 (9)	0.0178 (8)	−0.0107 (8)
O1	0.0352 (9)	0.0525 (9)	0.0489 (9)	−0.0083 (7)	0.0090 (7)	−0.0021 (7)
O2	0.0519 (10)	0.0524 (10)	0.0580 (10)	−0.0149 (8)	0.0129 (8)	−0.0181 (8)
O3	0.0341 (8)	0.0466 (8)	0.0442 (8)	−0.0070 (7)	0.0125 (6)	−0.0120 (7)
O4	0.1079 (15)	0.0542 (10)	0.0471 (11)	0.0141 (10)	0.0153 (10)	0.0083 (8)
O5	0.0769 (12)	0.0363 (9)	0.0641 (10)	0.0097 (8)	0.0087 (9)	−0.0089 (8)
O6	0.0446 (9)	0.0528 (9)	0.0674 (10)	−0.0145 (8)	0.0259 (8)	−0.0139 (8)
O7	0.0536 (10)	0.0524 (10)	0.0898 (12)	−0.0100 (8)	0.0391 (9)	−0.0266 (9)

C1—O1	1.375 (3)	C15—O7	1.345 (3)
C1—C2	1.380 (3)	C16—O7	1.434 (3)
C1—C6	1.388 (3)	C16—H16A	0.9600
C2—C3	1.370 (4)	C16—H16B	0.9600
C2—H2	0.9300	C16—H16C	0.9600
C3—C4	1.379 (4)	C17—N1	1.486 (3)
C3—H3	0.9300	C17—C19	1.523 (3)
C4—C5	1.368 (3)	C17—C18	1.530 (3)
C4—H4	0.9300	C17—C20	1.541 (3)
C5—C6	1.400 (3)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—C7	1.438 (3)	C18—H18C	0.9600
C7—C8	1.336 (3)	C19—H19A	0.9600
C7—O3	1.368 (2)	C19—H19B	0.9600
C8—C9	1.448 (3)	C19—H19C	0.9600
C8—C10	1.499 (3)	C20—C21	1.535 (3)
C9—O2	1.203 (2)	C20—H20A	0.9700
C9—O1	1.372 (3)	C20—H20B	0.9700
C10—C11	1.507 (3)	C21—C22	1.510 (4)
C10—C13	1.530 (3)	C21—C23	1.524 (4)
C10—H10	0.9800	C21—C24	1.531 (4)
C11—C12	1.370 (3)	C22—H22A	0.9600
C11—C15	1.429 (3)	C22—H22B	0.9600
C12—N1	1.327 (2)	C22—H22C	0.9600
C12—O3	1.372 (2)	C23—H23A	0.9600
C13—O4	1.188 (3)	C23—H23B	0.9600
C13—O5	1.321 (2)	C23—H23C	0.9600
C14—O5	1.443 (3)	C24—H24A	0.9600
C14—H14A	0.9600	C24—H24B	0.9600
C14—H14B	0.9600	C24—H24C	0.9600
C14—H14C	0.9600	N1—H1	0.8600
C15—O6	1.217 (2)
O1—C1—C2	116.82 (19)	H16B—C16—H16C	109.5
O1—C1—C6	121.28 (18)	N1—C17—C19	104.75 (17)
C2—C1—C6	121.9 (2)	N1—C17—C18	110.10 (17)
C3—C2—C1	118.5 (2)	C19—C17—C18	107.69 (19)
C3—C2—H2	120.8	N1—C17—C20	111.92 (16)
C1—C2—H2	120.8	C19—C17—C20	113.81 (18)
C2—C3—C4	121.0 (2)	C18—C17—C20	108.45 (18)
C2—C3—H3	119.5	C17—C18—H18A	109.5
C4—C3—H3	119.5	C17—C18—H18B	109.5
C5—C4—C3	120.6 (2)	H18A—C18—H18B	109.5
C5—C4—H4	119.7	C17—C18—H18C	109.5
C3—C4—H4	119.7	H18A—C18—H18C	109.5
C4—C5—C6	119.9 (2)	H18B—C18—H18C	109.5
C4—C5—H5	120.1	C17—C19—H19A	109.5
C6—C5—H5	120.1	C17—C19—H19B	109.5
C1—C6—C5	118.2 (2)	H19A—C19—H19B	109.5
C1—C6—C7	116.52 (19)	C17—C19—H19C	109.5
C5—C6—C7	125.24 (19)	H19A—C19—H19C	109.5
C8—C7—O3	123.17 (18)	H19B—C19—H19C	109.5
C8—C7—C6	122.59 (18)	C21—C20—C17	124.20 (19)
O3—C7—C6	114.24 (17)	C21—C20—H20A	106.3
C7—C8—C9	119.55 (19)	C17—C20—H20A	106.3
C7—C8—C10	121.96 (17)	C21—C20—H20B	106.3
C9—C8—C10	118.50 (17)	C17—C20—H20B	106.3
O2—C9—O1	117.22 (18)	H20A—C20—H20B	106.4
O2—C9—C8	125.0 (2)	C22—C21—C23	111.1 (3)
O1—C9—C8	117.73 (19)	C22—C21—C24	108.3 (3)
C8—C10—C11	109.38 (16)	C23—C21—C24	105.7 (3)
C8—C10—C13	109.61 (16)	C22—C21—C20	113.9 (2)
C11—C10—C13	109.78 (16)	C23—C21—C20	112.2 (2)
C8—C10—H10	109.4	C24—C21—C20	105.1 (2)
C11—C10—H10	109.4	C21—C22—H22A	109.5
C13—C10—H10	109.4	C21—C22—H22B	109.5
C12—C11—C15	118.54 (17)	H22A—C22—H22B	109.5
C12—C11—C10	121.39 (17)	C21—C22—H22C	109.5
C15—C11—C10	119.64 (17)	H22A—C22—H22C	109.5
N1—C12—C11	125.51 (18)	H22B—C22—H22C	109.5
N1—C12—O3	112.61 (16)	C21—C23—H23A	109.5
C11—C12—O3	121.87 (17)	C21—C23—H23B	109.5
O4—C13—O5	123.8 (2)	H23A—C23—H23B	109.5
O4—C13—C10	123.77 (19)	C21—C23—H23C	109.5
O5—C13—C10	112.47 (18)	H23A—C23—H23C	109.5
O5—C14—H14A	109.5	H23B—C23—H23C	109.5
O5—C14—H14B	109.5	C21—C24—H24A	109.5
H14A—C14—H14B	109.5	C21—C24—H24B	109.5
O5—C14—H14C	109.5	H24A—C24—H24B	109.5
H14A—C14—H14C	109.5	C21—C24—H24C	109.5
H14B—C14—H14C	109.5	H24A—C24—H24C	109.5
O6—C15—O7	121.03 (19)	H24B—C24—H24C	109.5
O6—C15—C11	127.07 (19)	C12—N1—C17	130.79 (17)
O7—C15—C11	111.89 (18)	C12—N1—H1	114.6
O7—C16—H16A	109.5	C17—N1—H1	114.6
O7—C16—H16B	109.5	C9—O1—C1	122.20 (16)
H16A—C16—H16B	109.5	C7—O3—C12	118.03 (15)
O7—C16—H16C	109.5	C13—O5—C14	116.13 (19)
H16A—C16—H16C	109.5	C15—O7—C16	116.12 (18)
O1—C1—C2—C3	179.0 (2)	C15—C11—C12—O3	−175.20 (17)
C6—C1—C2—C3	0.1 (3)	C10—C11—C12—O3	−2.7 (3)
C1—C2—C3—C4	−0.4 (4)	C8—C10—C13—O4	−65.5 (3)
C2—C3—C4—C5	0.4 (4)	C11—C10—C13—O4	54.7 (3)
C3—C4—C5—C6	−0.2 (4)	C8—C10—C13—O5	114.86 (19)
O1—C1—C6—C5	−178.78 (19)	C11—C10—C13—O5	−124.98 (18)
C2—C1—C6—C5	0.0 (3)	C12—C11—C15—O6	−7.8 (3)
O1—C1—C6—C7	0.8 (3)	C10—C11—C15—O6	179.6 (2)
C2—C1—C6—C7	179.6 (2)	C12—C11—C15—O7	171.88 (18)
C4—C5—C6—C1	0.0 (3)	C10—C11—C15—O7	−0.7 (3)
C4—C5—C6—C7	−179.6 (2)	N1—C17—C20—C21	60.1 (3)
C1—C6—C7—C8	−3.9 (3)	C19—C17—C20—C21	−58.4 (3)
C5—C6—C7—C8	175.7 (2)	C18—C17—C20—C21	−178.2 (2)
C1—C6—C7—O3	175.31 (17)	C17—C20—C21—C22	−55.2 (4)
C5—C6—C7—O3	−5.1 (3)	C17—C20—C21—C23	72.1 (3)
O3—C7—C8—C9	−174.87 (17)	C17—C20—C21—C24	−173.5 (2)
C6—C7—C8—C9	4.3 (3)	C11—C12—N1—C17	−166.6 (2)
O3—C7—C8—C10	4.9 (3)	O3—C12—N1—C17	13.7 (3)
C6—C7—C8—C10	−175.94 (18)	C19—C17—N1—C12	177.1 (2)
C7—C8—C9—O2	178.8 (2)	C18—C17—N1—C12	−67.3 (3)
C10—C8—C9—O2	−0.9 (3)	C20—C17—N1—C12	53.4 (3)
C7—C8—C9—O1	−1.6 (3)	O2—C9—O1—C1	178.21 (18)
C10—C8—C9—O1	178.63 (16)	C8—C9—O1—C1	−1.4 (3)
C7—C8—C10—C11	−19.0 (2)	C2—C1—O1—C9	−177.13 (18)
C9—C8—C10—C11	160.78 (17)	C6—C1—O1—C9	1.7 (3)
C7—C8—C10—C13	101.4 (2)	C8—C7—O3—C12	12.7 (3)
C9—C8—C10—C13	−78.8 (2)	C6—C7—O3—C12	−166.56 (16)
C8—C10—C11—C12	17.8 (2)	N1—C12—O3—C7	166.09 (16)
C13—C10—C11—C12	−102.5 (2)	C11—C12—O3—C7	−13.6 (3)
C8—C10—C11—C15	−169.79 (17)	O4—C13—O5—C14	−2.4 (3)
C13—C10—C11—C15	69.9 (2)	C10—C13—O5—C14	177.3 (2)
C15—C11—C12—N1	5.2 (3)	O6—C15—O7—C16	6.4 (3)
C10—C11—C12—N1	177.64 (18)	C11—C15—O7—C16	−173.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19C···O2i	0.96	2.58	3.458 (3)	153
C23—H23A···O6ii	0.96	2.54	3.255 (4)	131
C23—H23B···O1iii	0.96	2.55	3.509 (4)	174
N1—H1···O6	0.86	2.01	2.660 (2)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19C⋯O2i	0.96	2.58	3.458 (3)	153
C23—H23A⋯O6ii	0.96	2.54	3.255 (4)	131
C23—H23B⋯O1iii	0.96	2.55	3.509 (4)	174
N1—H1⋯O6	0.86	2.01	2.660 (2)	131

Symmetry codes: (i) ; (ii) ; (iii) .