3,5-Dimethyl-1-{2-[(5-methyl-1,3,4-thia-diazol-2-yl)sulfan-yl]acet-yl}-2,6-diphenylpiperidin-4-one.

In the title compound, C24H25N3O2S2, the piperidine ring adopts a distorted boat conformation. The phenyl rings subtend angles of 75.6 (1)° and 86.3 (1)° with the mean plane of the piperidine ring. In the crystal, mol-ecules are linked through a network C-H⋯N hydrogen bonds, forming zigzag chains along [100]. The thia-diazol ring methyl group is disordered over two positions with an occupancy ratio of 0.69 (4):0.31 (4).

Related literature

For the biological activity of piperidine derivatives, see: Aridoss et al. (2009 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶) and for asymmetry parameters, see: Nardelli (1983 ▶). For hydrogen-bond motifs, see: Bernstein et al.(1995 ▶).

Experimental

Crystal data

C24H25N3O2S2

M = 451.59

Orthorhombic,

a = 9.1342 (6) Å

b = 9.2874 (6) Å

c = 27.0454 (14) Å

V = 2294.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.30 × 0.30 × 0.25 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.927, T max = 0.938

10655 measured reflections

4215 independent reflections

3623 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.098

S = 1.06

4215 reflections

293 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 1461 Friedel pairs

Flack parameter: 0.26 (8)

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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813012014/ng5326sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813012014/ng5326Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813012014/ng5326Isup3.cml

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

C24H25N3O2S2	F(000) = 952
Mr = 451.59	Dx = 1.307 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4138 reflections
a = 9.1342 (6) Å	θ = 1.5–28.4°
b = 9.2874 (6) Å	µ = 0.26 mm−1
c = 27.0454 (14) Å	T = 293 K
V = 2294.3 (2) Å3	Block, white crystalline
Z = 4	0.30 × 0.30 × 0.25 mm

Bruker SMART APEXII CCD diffractometer	4215 independent reflections
Radiation source: fine-focus sealed tube	3623 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scans	θmax = 25.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→10
Tmin = 0.927, Tmax = 0.938	k = −10→11
10655 measured reflections	l = −32→32

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0407P)2 + 0.4037P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.003
4215 reflections	Δρmax = 0.18 e Å−3
293 parameters	Δρmin = −0.24 e Å−3
2 restraints	Absolute structure: Flack (1983), 1461 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.26 (8)

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)
C2	0.8537 (3)	0.3491 (3)	0.31092 (8)	0.0434 (6)
H2	0.9412	0.4016	0.3003	0.052*
C3	0.7285 (3)	0.4013 (3)	0.27855 (9)	0.0498 (6)
H3	0.7412	0.3594	0.2456	0.060*
C4	0.5804 (3)	0.3549 (3)	0.29802 (10)	0.0557 (7)
C5	0.5761 (3)	0.2856 (3)	0.34821 (9)	0.0468 (6)
H5	0.6113	0.1866	0.3442	0.056*
C6	0.6804 (2)	0.3605 (3)	0.38547 (8)	0.0409 (5)
H6	0.6351	0.4523	0.3948	0.049*
C7	0.6940 (2)	0.2704 (3)	0.43237 (9)	0.0420 (6)
C8	0.6392 (3)	0.3216 (3)	0.47632 (9)	0.0565 (7)
H8	0.5926	0.4105	0.4773	0.068*
C9	0.6530 (4)	0.2415 (4)	0.51908 (11)	0.0761 (10)
H9	0.6165	0.2776	0.5487	0.091*
C10	0.7197 (4)	0.1100 (4)	0.51842 (13)	0.0766 (10)
H10	0.7295	0.0570	0.5474	0.092*
C11	0.7717 (4)	0.0571 (4)	0.47490 (13)	0.0716 (9)
H11	0.8162	−0.0329	0.4741	0.086*
C12	0.7588 (3)	0.1361 (3)	0.43181 (10)	0.0559 (7)
H12	0.7941	0.0986	0.4022	0.067*
C13	0.8916 (3)	0.1899 (3)	0.30846 (8)	0.0431 (6)
C14	1.0060 (3)	0.1415 (3)	0.33779 (9)	0.0569 (7)
H14	1.0598	0.2074	0.3562	0.068*
C15	1.0411 (3)	−0.0013 (4)	0.34010 (12)	0.0689 (9)
H15	1.1161	−0.0316	0.3609	0.083*
C16	0.9671 (4)	−0.1006 (3)	0.31216 (12)	0.0705 (9)
H16	0.9906	−0.1978	0.3143	0.085*
C17	0.8584 (4)	−0.0551 (3)	0.28114 (12)	0.0667 (8)
H17	0.8097	−0.1209	0.2611	0.080*
C18	0.8208 (3)	0.0898 (3)	0.27956 (10)	0.0535 (7)
H18	0.7463	0.1197	0.2585	0.064*
C19	0.7301 (4)	0.5638 (3)	0.27324 (12)	0.0756 (9)
H19A	0.8236	0.5941	0.2608	0.113*
H19B	0.7130	0.6073	0.3049	0.113*
H19C	0.6546	0.5929	0.2506	0.113*
C20	0.4220 (3)	0.2764 (4)	0.36868 (12)	0.0714 (9)
H20A	0.4243	0.2312	0.4006	0.107*
H20B	0.3621	0.2205	0.3467	0.107*
H20C	0.3820	0.3715	0.3717	0.107*
C21	0.9216 (3)	0.4863 (3)	0.38323 (9)	0.0447 (6)
C22	0.8900 (3)	0.5401 (3)	0.43507 (9)	0.0444 (6)
H22A	0.9070	0.4641	0.4590	0.053*
H22B	0.7889	0.5711	0.4377	0.053*
C23	0.9909 (3)	0.7090 (3)	0.50966 (9)	0.0471 (6)
C24	0.9507 (4)	0.7112 (5)	0.59575 (11)	0.0869 (12)
N1	0.8240 (2)	0.3941 (2)	0.36250 (7)	0.0391 (4)
N2	1.0669 (3)	0.8047 (3)	0.53206 (9)	0.0749 (8)
N3	1.0440 (3)	0.8048 (3)	0.58237 (9)	0.0874 (10)
O1	0.4720 (3)	0.3740 (3)	0.27404 (9)	0.1004 (9)
O2	1.0350 (2)	0.5239 (2)	0.36260 (7)	0.0672 (6)
S1	1.01181 (9)	0.68920 (7)	0.44633 (2)	0.0565 (2)
S2	0.88298 (10)	0.60962 (11)	0.54817 (3)	0.0817 (3)
C25A	0.884 (3)	0.715 (3)	0.6474 (4)	0.123 (7)	0.69 (4)
H25A	0.8855	0.6198	0.6613	0.185*	0.69 (4)
H25B	0.7853	0.7490	0.6455	0.185*	0.69 (4)
H25C	0.9407	0.7784	0.6680	0.185*	0.69 (4)
C25B	0.951 (3)	0.649 (3)	0.6513 (6)	0.076 (6)	0.31 (4)
H25D	1.0483	0.6177	0.6598	0.113*	0.31 (4)
H25E	0.8853	0.5682	0.6534	0.113*	0.31 (4)
H25F	0.9202	0.7224	0.6738	0.113*	0.31 (4)

	U11	U22	U33	U12	U13	U23
C2	0.0469 (13)	0.0527 (15)	0.0307 (11)	−0.0076 (12)	0.0032 (10)	−0.0014 (10)
C3	0.0618 (16)	0.0515 (15)	0.0360 (13)	0.0021 (13)	−0.0031 (11)	−0.0025 (12)
C4	0.0517 (15)	0.0668 (18)	0.0485 (15)	0.0017 (13)	−0.0114 (12)	−0.0039 (13)
C5	0.0402 (13)	0.0516 (15)	0.0485 (14)	−0.0038 (11)	−0.0022 (11)	−0.0039 (12)
C6	0.0387 (12)	0.0446 (13)	0.0393 (12)	0.0024 (10)	0.0010 (10)	−0.0030 (11)
C7	0.0361 (12)	0.0488 (15)	0.0411 (13)	−0.0055 (11)	0.0021 (10)	−0.0002 (11)
C8	0.0613 (17)	0.0627 (17)	0.0456 (15)	−0.0139 (14)	0.0082 (13)	−0.0046 (14)
C9	0.088 (2)	0.100 (3)	0.0400 (15)	−0.036 (2)	0.0062 (15)	−0.0004 (18)
C10	0.074 (2)	0.093 (3)	0.063 (2)	−0.032 (2)	−0.0199 (17)	0.030 (2)
C11	0.0616 (19)	0.071 (2)	0.082 (2)	0.0007 (16)	−0.0033 (17)	0.0289 (19)
C12	0.0499 (14)	0.0580 (16)	0.0597 (17)	0.0043 (13)	0.0076 (13)	0.0088 (14)
C13	0.0428 (13)	0.0522 (14)	0.0344 (11)	−0.0030 (12)	0.0071 (10)	−0.0059 (11)
C14	0.0457 (14)	0.0730 (18)	0.0520 (15)	0.0061 (15)	0.0007 (13)	−0.0141 (13)
C15	0.0548 (18)	0.083 (2)	0.0684 (19)	0.0264 (17)	0.0023 (15)	−0.0010 (17)
C16	0.069 (2)	0.0571 (17)	0.085 (2)	0.0112 (17)	0.0170 (17)	−0.0013 (17)
C17	0.072 (2)	0.0482 (16)	0.080 (2)	−0.0047 (15)	0.0036 (17)	−0.0152 (15)
C18	0.0551 (16)	0.0556 (16)	0.0499 (15)	−0.0007 (13)	−0.0023 (12)	−0.0042 (13)
C19	0.096 (3)	0.0586 (18)	0.072 (2)	0.0069 (18)	0.0009 (19)	0.0069 (17)
C20	0.0438 (15)	0.100 (3)	0.0701 (19)	−0.0074 (16)	0.0006 (14)	−0.0088 (19)
C21	0.0460 (14)	0.0477 (14)	0.0404 (13)	−0.0020 (12)	0.0018 (11)	−0.0019 (11)
C22	0.0424 (12)	0.0435 (13)	0.0474 (14)	−0.0041 (11)	0.0012 (11)	−0.0111 (11)
C23	0.0478 (13)	0.0401 (13)	0.0533 (14)	−0.0038 (12)	−0.0056 (12)	−0.0073 (11)
C24	0.085 (2)	0.128 (3)	0.0478 (16)	−0.058 (2)	0.0071 (16)	−0.0245 (19)
N1	0.0402 (10)	0.0430 (11)	0.0342 (9)	−0.0039 (9)	0.0017 (8)	−0.0036 (9)
N2	0.097 (2)	0.0737 (17)	0.0540 (14)	−0.0434 (16)	0.0062 (13)	−0.0155 (13)
N3	0.106 (2)	0.105 (2)	0.0513 (14)	−0.057 (2)	0.0087 (14)	−0.0253 (15)
O1	0.0660 (14)	0.159 (2)	0.0759 (14)	−0.0036 (16)	−0.0281 (12)	0.0246 (16)
O2	0.0582 (12)	0.0878 (14)	0.0554 (11)	−0.0297 (11)	0.0149 (10)	−0.0213 (10)
S1	0.0768 (5)	0.0470 (3)	0.0457 (3)	−0.0182 (3)	0.0007 (3)	−0.0046 (3)
S2	0.0872 (6)	0.1083 (7)	0.0495 (4)	−0.0573 (5)	0.0084 (4)	−0.0189 (4)
C25A	0.122 (10)	0.190 (16)	0.058 (4)	−0.076 (11)	0.007 (5)	−0.031 (6)
C25B	0.077 (11)	0.117 (14)	0.033 (5)	−0.028 (9)	0.015 (6)	−0.015 (6)

C2—N1	1.481 (3)	C16—C17	1.367 (4)
C2—C3	1.519 (3)	C16—H16	0.9300
C2—C13	1.520 (3)	C17—C18	1.389 (4)
C2—H2	0.9800	C17—H17	0.9300
C3—C4	1.515 (4)	C18—H18	0.9300
C3—C19	1.516 (4)	C19—H19A	0.9600
C3—H3	0.9800	C19—H19B	0.9600
C4—O1	1.197 (3)	C19—H19C	0.9600
C4—C5	1.503 (4)	C20—H20A	0.9600
C5—C20	1.515 (4)	C20—H20B	0.9600
C5—C6	1.552 (3)	C20—H20C	0.9600
C5—H5	0.9800	C21—O2	1.227 (3)
C6—N1	1.484 (3)	C21—N1	1.357 (3)
C6—C7	1.525 (3)	C21—C22	1.516 (3)
C6—H6	0.9800	C22—S1	1.802 (2)
C7—C8	1.375 (4)	C22—H22A	0.9700
C7—C12	1.381 (4)	C22—H22B	0.9700
C8—C9	1.380 (4)	C23—N2	1.280 (3)
C8—H8	0.9300	C23—S2	1.705 (3)
C9—C10	1.365 (5)	C23—S1	1.733 (3)
C9—H9	0.9300	C24—N3	1.270 (4)
C10—C11	1.361 (5)	C24—C25A	1.523 (10)
C10—H10	0.9300	C24—C25B	1.61 (2)
C11—C12	1.382 (4)	C24—S2	1.711 (3)
C11—H11	0.9300	N2—N3	1.377 (3)
C12—H12	0.9300	C25A—H25A	0.9600
C13—C18	1.376 (4)	C25A—H25B	0.9600
C13—C14	1.387 (4)	C25A—H25C	0.9600
C14—C15	1.366 (4)	C25B—H25D	0.9600
C14—H14	0.9300	C25B—H25E	0.9600
C15—C16	1.370 (5)	C25B—H25F	0.9600
C15—H15	0.9300
N1—C2—C3	108.3 (2)	C17—C16—C15	119.3 (3)
N1—C2—C13	110.96 (19)	C17—C16—H16	120.4
C3—C2—C13	117.2 (2)	C15—C16—H16	120.4
N1—C2—H2	106.6	C16—C17—C18	119.9 (3)
C3—C2—H2	106.6	C16—C17—H17	120.1
C13—C2—H2	106.6	C18—C17—H17	120.1
C4—C3—C19	108.9 (2)	C13—C18—C17	121.4 (3)
C4—C3—C2	112.4 (2)	C13—C18—H18	119.3
C19—C3—C2	111.4 (2)	C17—C18—H18	119.3
C4—C3—H3	108.0	C3—C19—H19A	109.5
C19—C3—H3	108.0	C3—C19—H19B	109.5
C2—C3—H3	108.0	H19A—C19—H19B	109.5
O1—C4—C5	122.1 (3)	C3—C19—H19C	109.5
O1—C4—C3	120.6 (3)	H19A—C19—H19C	109.5
C5—C4—C3	117.3 (2)	H19B—C19—H19C	109.5
C4—C5—C20	112.2 (2)	C5—C20—H20A	109.5
C4—C5—C6	112.2 (2)	C5—C20—H20B	109.5
C20—C5—C6	111.0 (2)	H20A—C20—H20B	109.5
C4—C5—H5	107.0	C5—C20—H20C	109.5
C20—C5—H5	107.0	H20A—C20—H20C	109.5
C6—C5—H5	107.0	H20B—C20—H20C	109.5
N1—C6—C7	113.06 (18)	O2—C21—N1	123.1 (2)
N1—C6—C5	111.39 (18)	O2—C21—C22	119.2 (2)
C7—C6—C5	110.1 (2)	N1—C21—C22	117.7 (2)
N1—C6—H6	107.3	C21—C22—S1	106.97 (17)
C7—C6—H6	107.3	C21—C22—H22A	110.3
C5—C6—H6	107.3	S1—C22—H22A	110.3
C8—C7—C12	118.5 (2)	C21—C22—H22B	110.3
C8—C7—C6	120.0 (2)	S1—C22—H22B	110.3
C12—C7—C6	121.4 (2)	H22A—C22—H22B	108.6
C7—C8—C9	120.3 (3)	N2—C23—S2	113.6 (2)
C7—C8—H8	119.8	N2—C23—S1	118.8 (2)
C9—C8—H8	119.8	S2—C23—S1	127.58 (15)
C10—C9—C8	120.8 (3)	N3—C24—C25A	120.8 (5)
C10—C9—H9	119.6	N3—C24—C25B	120.7 (8)
C8—C9—H9	119.6	N3—C24—S2	113.9 (2)
C11—C10—C9	119.3 (3)	C25A—C24—S2	124.0 (4)
C11—C10—H10	120.3	C25B—C24—S2	120.2 (8)
C9—C10—H10	120.3	C21—N1—C2	116.55 (19)
C10—C11—C12	120.6 (3)	C21—N1—C6	122.68 (19)
C10—C11—H11	119.7	C2—N1—C6	119.78 (18)
C12—C11—H11	119.7	C23—N2—N3	112.7 (2)
C7—C12—C11	120.4 (3)	C24—N3—N2	112.5 (2)
C7—C12—H12	119.8	C23—S1—C22	100.39 (12)
C11—C12—H12	119.8	C23—S2—C24	87.25 (14)
C18—C13—C14	117.4 (2)	C24—C25A—H25A	109.5
C18—C13—C2	125.1 (2)	C24—C25A—H25B	109.5
C14—C13—C2	117.5 (2)	C24—C25A—H25C	109.5
C15—C14—C13	121.2 (3)	C24—C25B—H25D	109.5
C15—C14—H14	119.4	C24—C25B—H25E	109.5
C13—C14—H14	119.4	H25D—C25B—H25E	109.5
C14—C15—C16	120.8 (3)	C24—C25B—H25F	109.5
C14—C15—H15	119.6	H25D—C25B—H25F	109.5
C16—C15—H15	119.6	H25E—C25B—H25F	109.5
N1—C2—C3—C4	−52.8 (3)	C13—C14—C15—C16	2.2 (5)
C13—C2—C3—C4	73.6 (3)	C14—C15—C16—C17	1.0 (5)
N1—C2—C3—C19	69.8 (3)	C15—C16—C17—C18	−2.2 (5)
C13—C2—C3—C19	−163.8 (2)	C14—C13—C18—C17	2.5 (4)
C19—C3—C4—O1	64.1 (4)	C2—C13—C18—C17	−177.1 (3)
C2—C3—C4—O1	−171.9 (3)	C16—C17—C18—C13	0.5 (5)
C19—C3—C4—C5	−115.6 (3)	O2—C21—C22—S1	15.4 (3)
C2—C3—C4—C5	8.4 (3)	N1—C21—C22—S1	−166.73 (18)
O1—C4—C5—C20	−13.2 (4)	O2—C21—N1—C2	−5.2 (4)
C3—C4—C5—C20	166.4 (3)	C22—C21—N1—C2	177.0 (2)
O1—C4—C5—C6	−139.0 (3)	O2—C21—N1—C6	−173.8 (2)
C3—C4—C5—C6	40.6 (3)	C22—C21—N1—C6	8.5 (3)
C4—C5—C6—N1	−43.1 (3)	C3—C2—N1—C21	−117.4 (2)
C20—C5—C6—N1	−169.6 (2)	C13—C2—N1—C21	112.6 (2)
C4—C5—C6—C7	−169.4 (2)	C3—C2—N1—C6	51.5 (3)
C20—C5—C6—C7	64.1 (3)	C13—C2—N1—C6	−78.4 (3)
N1—C6—C7—C8	121.4 (2)	C7—C6—N1—C21	−70.2 (3)
C5—C6—C7—C8	−113.2 (3)	C5—C6—N1—C21	165.2 (2)
N1—C6—C7—C12	−59.6 (3)	C7—C6—N1—C2	121.6 (2)
C5—C6—C7—C12	65.8 (3)	C5—C6—N1—C2	−3.0 (3)
C12—C7—C8—C9	1.9 (4)	S2—C23—N2—N3	0.2 (4)
C6—C7—C8—C9	−179.0 (2)	S1—C23—N2—N3	−177.5 (2)
C7—C8—C9—C10	−0.7 (5)	C25A—C24—N3—N2	−166.3 (15)
C8—C9—C10—C11	−0.6 (5)	C25B—C24—N3—N2	156.0 (14)
C9—C10—C11—C12	0.7 (5)	S2—C24—N3—N2	1.3 (5)
C8—C7—C12—C11	−1.8 (4)	C23—N2—N3—C24	−1.0 (5)
C6—C7—C12—C11	179.2 (3)	N2—C23—S1—C22	177.6 (2)
C10—C11—C12—C7	0.5 (5)	S2—C23—S1—C22	0.2 (2)
N1—C2—C13—C18	124.6 (2)	C21—C22—S1—C23	−167.14 (17)
C3—C2—C13—C18	−0.5 (3)	N2—C23—S2—C24	0.4 (3)
N1—C2—C13—C14	−55.0 (3)	S1—C23—S2—C24	177.8 (2)
C3—C2—C13—C14	179.8 (2)	N3—C24—S2—C23	−1.0 (3)
C18—C13—C14—C15	−3.8 (4)	C25A—C24—S2—C23	166.2 (16)
C2—C13—C14—C15	175.8 (3)	C25B—C24—S2—C23	−155.8 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···N3i	0.98	2.48	3.460 (4)	175
C22—H22B···N2i	0.97	2.47	3.403 (4)	161
C22—H22B···N3i	0.97	2.57	3.505 (4)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯N3i	0.98	2.48	3.460 (4)	175
C22—H22B⋯N2i	0.97	2.47	3.403 (4)	161
C22—H22B⋯N3i	0.97	2.57	3.505 (4)	161

Symmetry code: (i) .