2,2'-[(3-Bromo-4-hy-droxy-5-meth-oxy-phen-yl)methyl-idene]bis-(3-hy-droxy-5,5-dimethyl-cyclo-hex-2-en-1-one).

In the title compound, C(24)H(29)BrO(6), the dihedral angle between the cyclo-hexenone mean planes is 57.63 (2)° while the dihedral angles between the benzene ring and the cyclo-hexenone mean planes are 58.42 (2) and 69.08 (3)°. The two cyclo-hexenone rings both show an envelope conformation, with the C atom bearing two methyl groups as the flap atom in each ring. Two intra-molecular O-H⋯O hydrogen bonds occur. In the crystal, molecules are linked via pairs of O-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For the synthesis of bis­dimedones, see: Vanag & Stankevich (1960 ▶); Hilderbrand & Weissleder (2007 ▶). For their pharmaceutical properties, see: Lambert et al. (1997 ▶); Poupelin et al. (1978 ▶); Hideo (1981 ▶); Selvanayagam et al. (1996 ▶); Jonathan et al. (1988 ▶). For crystal structures of related xanthene derivatives, see: Odabaşoğlu et al. (2008 ▶); Mehdi et al. (2011 ▶); Ravikumar et al. (2012 ▶); Sureshbabu & Sughanya (2012 ▶). For the assignment of ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H29BrO6

M = 493.38

Monoclinic,

a = 11.7479 (4) Å

b = 19.3706 (6) Å

c = 11.5958 (4) Å

β = 118.365 (1)°

V = 2321.97 (13) Å3

Z = 4

Mo Kα radiation

μ = 1.81 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.604, T max = 0.765

22187 measured reflections

4313 independent reflections

3395 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.095

S = 1.04

4313 reflections

285 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.51 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037853/im2397sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037853/im2397Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037853/im2397Isup3.cml

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

C24H29BrO6	F(000) = 1024
Mr = 493.38	Dx = 1.411 Mg m−3
Monoclinic, P21/c	Melting point: 491 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.7479 (4) Å	Cell parameters from 7579 reflections
b = 19.3706 (6) Å	θ = 2.1–25.4°
c = 11.5958 (4) Å	µ = 1.81 mm−1
β = 118.365 (1)°	T = 296 K
V = 2321.97 (13) Å3	Block, yellow
Z = 4	0.30 × 0.20 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	4313 independent reflections
Radiation source: fine-focus sealed tube	3395 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
ω and φ scan	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→14
Tmin = 0.604, Tmax = 0.765	k = −23→19
22187 measured reflections	l = −14→13

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0471P)2 + 1.1375P] where P = (Fo2 + 2Fc2)/3
4313 reflections	(Δ/σ)max = 0.002
285 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	1.2613 (3)	0.26315 (17)	0.2601 (3)	0.0659 (9)
H1A	1.2246	0.3011	0.2005	0.099*
H1B	1.2871	0.2277	0.2194	0.099*
H1C	1.3354	0.2788	0.3383	0.099*
C2	1.1247 (3)	0.28939 (14)	0.3665 (3)	0.0577 (7)
H2A	1.0575	0.2722	0.3835	0.087*
H2B	1.0948	0.3300	0.3128	0.087*
H2C	1.1994	0.3007	0.4479	0.087*
C3	1.1605 (2)	0.23420 (13)	0.2953 (2)	0.0417 (6)
C4	1.0407 (2)	0.21187 (13)	0.1703 (2)	0.0397 (5)
H4A	0.9988	0.2525	0.1187	0.048*
H4B	1.0674	0.1831	0.1190	0.048*
C5	0.9453 (2)	0.17286 (11)	0.1961 (2)	0.0328 (5)
C6	0.98674 (19)	0.12637 (11)	0.3011 (2)	0.0306 (5)
C7	1.1163 (2)	0.12824 (11)	0.3968 (2)	0.0346 (5)
C8	1.2146 (2)	0.17062 (13)	0.3816 (2)	0.0407 (6)
H8A	1.2567	0.1417	0.3448	0.049*
H8B	1.2801	0.1853	0.4678	0.049*
C9	0.89559 (19)	0.07694 (11)	0.3184 (2)	0.0303 (5)
H9	0.9536	0.0432	0.3824	0.036*
C10	0.8246 (2)	0.10924 (11)	0.3857 (2)	0.0310 (5)
C11	0.7081 (2)	0.14463 (11)	0.3181 (2)	0.0341 (5)
C12	0.6363 (2)	0.17136 (13)	0.3861 (3)	0.0460 (6)
H12A	0.5443	0.1697	0.3257	0.055*
H12B	0.6597	0.2193	0.4093	0.055*
C13	0.6627 (2)	0.13151 (14)	0.5090 (3)	0.0468 (6)
C14	0.8083 (2)	0.12723 (14)	0.5938 (2)	0.0449 (6)
H14A	0.8404	0.1723	0.6321	0.054*
H14B	0.8274	0.0952	0.6651	0.054*
C15	0.8790 (2)	0.10448 (12)	0.5219 (2)	0.0365 (5)
C16	0.6047 (3)	0.05929 (17)	0.4753 (3)	0.0685 (9)
H16A	0.5151	0.0624	0.4109	0.103*
H16B	0.6119	0.0375	0.5529	0.103*
H16C	0.6504	0.0325	0.4410	0.103*
C17	0.6055 (3)	0.16999 (19)	0.5846 (3)	0.0728 (9)
H17A	0.6405	0.2158	0.6044	0.109*
H17B	0.6268	0.1459	0.6647	0.109*
H17C	0.5132	0.1724	0.5322	0.109*
C18	0.8103 (2)	0.03309 (11)	0.1981 (2)	0.0310 (5)
C19	0.8378 (2)	0.02503 (11)	0.0962 (2)	0.0353 (5)
H19	0.9051	0.0498	0.0954	0.042*
C20	0.7654 (2)	−0.01994 (12)	−0.0051 (2)	0.0379 (5)
C21	0.6656 (2)	−0.05795 (12)	−0.0079 (2)	0.0348 (5)
C22	0.6402 (2)	−0.05102 (12)	0.0971 (2)	0.0339 (5)
C23	0.7111 (2)	−0.00615 (12)	0.1986 (2)	0.0329 (5)
H23	0.6926	−0.0021	0.2678	0.039*
C24	0.5090 (2)	−0.09167 (15)	0.1878 (3)	0.0520 (7)
H24A	0.5833	−0.1052	0.2678	0.078*
H24B	0.4397	−0.1236	0.1681	0.078*
H24C	0.4825	−0.0462	0.1978	0.078*
O1	1.16091 (15)	0.09328 (9)	0.50350 (16)	0.0475 (4)
H1	1.1050	0.0897	0.5264	0.057*
O2	0.82574 (15)	0.18263 (9)	0.11431 (16)	0.0440 (4)
O3	0.65632 (14)	0.15767 (9)	0.19490 (15)	0.0423 (4)
H3	0.7021	0.1421	0.1654	0.051*
O4	0.99402 (16)	0.08135 (9)	0.59430 (16)	0.0464 (4)
O5	0.59553 (16)	−0.10130 (9)	−0.10871 (17)	0.0499 (5)
H5A	0.5327	−0.1152	−0.1027	0.060*
O6	0.54020 (16)	−0.09165 (9)	0.08626 (16)	0.0461 (4)
Br1	0.80247 (3)	−0.027192 (18)	−0.14649 (3)	0.06469 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0487 (16)	0.076 (2)	0.072 (2)	−0.0183 (15)	0.0283 (15)	0.0118 (16)
C2	0.0609 (17)	0.0437 (16)	0.0598 (18)	−0.0099 (14)	0.0214 (14)	−0.0080 (13)
C3	0.0372 (12)	0.0411 (14)	0.0468 (14)	−0.0109 (11)	0.0200 (11)	−0.0024 (11)
C4	0.0404 (13)	0.0394 (14)	0.0424 (13)	−0.0010 (11)	0.0222 (11)	0.0035 (10)
C5	0.0335 (11)	0.0303 (12)	0.0341 (12)	−0.0008 (9)	0.0156 (10)	−0.0040 (9)
C6	0.0285 (10)	0.0265 (12)	0.0351 (12)	−0.0011 (9)	0.0137 (9)	−0.0023 (9)
C7	0.0341 (11)	0.0296 (12)	0.0379 (12)	0.0008 (10)	0.0153 (10)	−0.0018 (10)
C8	0.0280 (11)	0.0456 (15)	0.0456 (14)	−0.0060 (10)	0.0152 (10)	−0.0022 (11)
C9	0.0280 (10)	0.0271 (12)	0.0315 (11)	−0.0016 (9)	0.0105 (9)	0.0011 (9)
C10	0.0311 (11)	0.0259 (12)	0.0352 (12)	−0.0065 (9)	0.0152 (9)	−0.0019 (9)
C11	0.0303 (11)	0.0276 (12)	0.0409 (13)	−0.0081 (9)	0.0141 (10)	−0.0047 (9)
C12	0.0352 (12)	0.0471 (15)	0.0557 (16)	−0.0010 (11)	0.0217 (12)	−0.0104 (12)
C13	0.0421 (13)	0.0542 (17)	0.0528 (15)	−0.0160 (12)	0.0295 (12)	−0.0129 (12)
C14	0.0467 (14)	0.0525 (16)	0.0411 (14)	−0.0143 (12)	0.0255 (12)	−0.0080 (11)
C15	0.0379 (12)	0.0300 (12)	0.0402 (13)	−0.0094 (10)	0.0175 (11)	−0.0027 (10)
C16	0.0684 (19)	0.072 (2)	0.076 (2)	−0.0374 (17)	0.0432 (17)	−0.0181 (17)
C17	0.0594 (18)	0.099 (3)	0.078 (2)	−0.0160 (18)	0.0469 (17)	−0.0260 (19)
C18	0.0276 (10)	0.0262 (12)	0.0342 (11)	0.0003 (9)	0.0107 (9)	−0.0006 (9)
C19	0.0285 (11)	0.0355 (13)	0.0424 (13)	−0.0033 (9)	0.0173 (10)	−0.0054 (10)
C20	0.0345 (12)	0.0436 (14)	0.0375 (12)	0.0020 (10)	0.0188 (10)	−0.0048 (10)
C21	0.0308 (11)	0.0318 (12)	0.0350 (12)	0.0002 (10)	0.0100 (10)	−0.0054 (9)
C22	0.0288 (11)	0.0285 (12)	0.0398 (12)	−0.0036 (9)	0.0125 (10)	0.0015 (10)
C23	0.0344 (12)	0.0310 (12)	0.0331 (12)	−0.0013 (10)	0.0159 (10)	0.0014 (9)
C24	0.0421 (14)	0.0511 (17)	0.0687 (18)	−0.0103 (12)	0.0310 (13)	0.0051 (13)
O1	0.0329 (8)	0.0556 (11)	0.0452 (10)	−0.0014 (8)	0.0115 (8)	0.0117 (8)
O2	0.0321 (8)	0.0451 (10)	0.0447 (9)	0.0018 (7)	0.0101 (7)	0.0096 (8)
O3	0.0345 (8)	0.0473 (10)	0.0418 (10)	0.0010 (7)	0.0153 (7)	0.0044 (8)
O4	0.0424 (9)	0.0513 (11)	0.0361 (9)	0.0028 (8)	0.0110 (8)	0.0070 (8)
O5	0.0421 (9)	0.0560 (11)	0.0485 (10)	−0.0165 (8)	0.0189 (8)	−0.0213 (8)
O6	0.0437 (9)	0.0443 (10)	0.0461 (10)	−0.0162 (8)	0.0179 (8)	−0.0066 (8)
Br1	0.0637 (2)	0.0859 (3)	0.0594 (2)	−0.01735 (16)	0.04152 (16)	−0.02778 (15)

C1—C3	1.530 (3)	C13—C14	1.517 (3)
C1—H1A	0.9600	C13—C16	1.523 (4)
C1—H1B	0.9600	C13—C17	1.528 (4)
C1—H1C	0.9600	C14—C15	1.497 (3)
C2—C3	1.526 (4)	C14—H14A	0.9700
C2—H2A	0.9600	C14—H14B	0.9700
C2—H2B	0.9600	C15—O4	1.286 (3)
C2—H2C	0.9600	C16—H16A	0.9600
C3—C8	1.522 (3)	C16—H16B	0.9600
C3—C4	1.527 (3)	C16—H16C	0.9600
C4—C5	1.496 (3)	C17—H17A	0.9600
C4—H4A	0.9700	C17—H17B	0.9600
C4—H4B	0.9700	C17—H17C	0.9600
C5—O2	1.282 (3)	C18—C19	1.374 (3)
C5—C6	1.402 (3)	C18—C23	1.393 (3)
C6—C7	1.394 (3)	C19—C20	1.384 (3)
C6—C9	1.520 (3)	C19—H19	0.9300
C7—O1	1.284 (3)	C20—C21	1.371 (3)
C7—C8	1.494 (3)	C20—Br1	1.891 (2)
C8—H8A	0.9700	C21—O5	1.355 (3)
C8—H8B	0.9700	C21—C22	1.392 (3)
C9—C10	1.521 (3)	C22—O6	1.369 (3)
C9—C18	1.531 (3)	C22—C23	1.379 (3)
C9—H9	0.9800	C23—H23	0.9300
C10—C11	1.392 (3)	C24—O6	1.390 (3)
C10—C15	1.397 (3)	C24—H24A	0.9600
C11—O3	1.284 (3)	C24—H24B	0.9600
C11—C12	1.494 (3)	C24—H24C	0.9600
C12—C13	1.518 (4)	O1—H1	0.8200
C12—H12A	0.9700	O3—H3	0.8200
C12—H12B	0.9700	O5—H5A	0.8200
C3—C1—H1A	109.5	H12A—C12—H12B	107.7
C3—C1—H1B	109.5	C14—C13—C12	107.49 (19)
H1A—C1—H1B	109.5	C14—C13—C16	110.2 (2)
C3—C1—H1C	109.5	C12—C13—C16	111.1 (2)
H1A—C1—H1C	109.5	C14—C13—C17	108.8 (2)
H1B—C1—H1C	109.5	C12—C13—C17	110.0 (2)
C3—C2—H2A	109.5	C16—C13—C17	109.3 (2)
C3—C2—H2B	109.5	C15—C14—C13	114.1 (2)
H2A—C2—H2B	109.5	C15—C14—H14A	108.7
C3—C2—H2C	109.5	C13—C14—H14A	108.7
H2A—C2—H2C	109.5	C15—C14—H14B	108.7
H2B—C2—H2C	109.5	C13—C14—H14B	108.7
C8—C3—C4	107.66 (19)	H14A—C14—H14B	107.6
C8—C3—C2	110.3 (2)	O4—C15—C10	122.4 (2)
C4—C3—C2	110.2 (2)	O4—C15—C14	115.3 (2)
C8—C3—C1	109.7 (2)	C10—C15—C14	122.2 (2)
C4—C3—C1	109.4 (2)	C13—C16—H16A	109.5
C2—C3—C1	109.5 (2)	C13—C16—H16B	109.5
C5—C4—C3	113.19 (19)	H16A—C16—H16B	109.5
C5—C4—H4A	108.9	C13—C16—H16C	109.5
C3—C4—H4A	108.9	H16A—C16—H16C	109.5
C5—C4—H4B	108.9	H16B—C16—H16C	109.5
C3—C4—H4B	108.9	C13—C17—H17A	109.5
H4A—C4—H4B	107.8	C13—C17—H17B	109.5
O2—C5—C6	122.9 (2)	H17A—C17—H17B	109.5
O2—C5—C4	116.1 (2)	C13—C17—H17C	109.5
C6—C5—C4	120.93 (19)	H17A—C17—H17C	109.5
C7—C6—C5	118.1 (2)	H17B—C17—H17C	109.5
C7—C6—C9	118.84 (19)	C19—C18—C23	118.7 (2)
C5—C6—C9	122.94 (18)	C19—C18—C9	121.83 (19)
O1—C7—C6	123.0 (2)	C23—C18—C9	119.05 (19)
O1—C7—C8	114.75 (19)	C18—C19—C20	120.1 (2)
C6—C7—C8	122.2 (2)	C18—C19—H19	120.0
C7—C8—C3	114.66 (18)	C20—C19—H19	120.0
C7—C8—H8A	108.6	C21—C20—C19	122.1 (2)
C3—C8—H8A	108.6	C21—C20—Br1	119.08 (17)
C7—C8—H8B	108.6	C19—C20—Br1	118.78 (17)
C3—C8—H8B	108.6	O5—C21—C20	121.0 (2)
H8A—C8—H8B	107.6	O5—C21—C22	121.3 (2)
C6—C9—C10	113.66 (17)	C20—C21—C22	117.6 (2)
C6—C9—C18	115.23 (17)	O6—C22—C23	125.8 (2)
C10—C9—C18	114.48 (17)	O6—C22—C21	113.30 (19)
C6—C9—H9	103.9	C23—C22—C21	120.9 (2)
C10—C9—H9	103.9	C22—C23—C18	120.5 (2)
C18—C9—H9	103.9	C22—C23—H23	119.7
C11—C10—C15	118.0 (2)	C18—C23—H23	119.7
C11—C10—C9	123.07 (19)	O6—C24—H24A	109.5
C15—C10—C9	118.96 (19)	O6—C24—H24B	109.5
O3—C11—C10	122.9 (2)	H24A—C24—H24B	109.5
O3—C11—C12	115.5 (2)	O6—C24—H24C	109.5
C10—C11—C12	121.6 (2)	H24A—C24—H24C	109.5
C11—C12—C13	113.9 (2)	H24B—C24—H24C	109.5
C11—C12—H12A	108.8	C7—O1—H1	109.5
C13—C12—H12A	108.8	C11—O3—H3	109.5
C11—C12—H12B	108.8	C21—O5—H5A	109.5
C13—C12—H12B	108.8	C22—O6—C24	118.84 (19)
C8—C3—C4—C5	51.8 (3)	C11—C12—C13—C16	−69.2 (3)
C2—C3—C4—C5	−68.5 (3)	C11—C12—C13—C17	169.7 (2)
C1—C3—C4—C5	171.0 (2)	C12—C13—C14—C15	−48.5 (3)
C3—C4—C5—O2	145.4 (2)	C16—C13—C14—C15	72.7 (3)
C3—C4—C5—C6	−37.2 (3)	C17—C13—C14—C15	−167.5 (2)
O2—C5—C6—C7	−169.1 (2)	C11—C10—C15—O4	−170.2 (2)
C4—C5—C6—C7	13.7 (3)	C9—C10—C15—O4	8.7 (3)
O2—C5—C6—C9	7.6 (3)	C11—C10—C15—C14	8.6 (3)
C4—C5—C6—C9	−169.5 (2)	C9—C10—C15—C14	−172.5 (2)
C5—C6—C7—O1	172.3 (2)	C13—C14—C15—O4	−160.8 (2)
C9—C6—C7—O1	−4.6 (3)	C13—C14—C15—C10	20.3 (3)
C5—C6—C7—C8	−8.7 (3)	C6—C9—C18—C19	16.9 (3)
C9—C6—C7—C8	174.4 (2)	C10—C9—C18—C19	151.5 (2)
O1—C7—C8—C3	−153.3 (2)	C6—C9—C18—C23	−170.77 (19)
C6—C7—C8—C3	27.6 (3)	C10—C9—C18—C23	−36.2 (3)
C4—C3—C8—C7	−47.4 (3)	C23—C18—C19—C20	1.7 (3)
C2—C3—C8—C7	72.9 (3)	C9—C18—C19—C20	174.1 (2)
C1—C3—C8—C7	−166.4 (2)	C18—C19—C20—C21	−0.4 (3)
C7—C6—C9—C10	93.2 (2)	C18—C19—C20—Br1	177.86 (17)
C5—C6—C9—C10	−83.6 (3)	C19—C20—C21—O5	179.5 (2)
C7—C6—C9—C18	−131.8 (2)	Br1—C20—C21—O5	1.3 (3)
C5—C6—C9—C18	51.4 (3)	C19—C20—C21—C22	−1.3 (3)
C6—C9—C10—C11	87.2 (2)	Br1—C20—C21—C22	−179.51 (17)
C18—C9—C10—C11	−48.1 (3)	O5—C21—C22—O6	0.0 (3)
C6—C9—C10—C15	−91.7 (2)	C20—C21—C22—O6	−179.2 (2)
C18—C9—C10—C15	133.0 (2)	O5—C21—C22—C23	−179.2 (2)
C15—C10—C11—O3	173.1 (2)	C20—C21—C22—C23	1.6 (3)
C9—C10—C11—O3	−5.7 (3)	O6—C22—C23—C18	−179.4 (2)
C15—C10—C11—C12	−5.5 (3)	C21—C22—C23—C18	−0.2 (3)
C9—C10—C11—C12	175.6 (2)	C19—C18—C23—C22	−1.4 (3)
O3—C11—C12—C13	155.0 (2)	C9—C18—C23—C22	−174.0 (2)
C10—C11—C12—C13	−26.3 (3)	C23—C22—O6—C24	−3.6 (3)
C11—C12—C13—C14	51.4 (3)	C21—C22—O6—C24	177.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O3i	0.82	2.12	2.852 (2)	149
O3—H3···O2	0.82	1.97	2.615 (2)	135
O1—H1···O4	0.82	1.82	2.640 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O3i	0.82	2.12	2.852 (2)	149
O3—H3⋯O2	0.82	1.97	2.615 (2)	135
O1—H1⋯O4	0.82	1.82	2.640 (2)	174

Symmetry code: (i) .