1-Benzyl-3-[(trimethyl­sil­yl)meth­yl]benzimidazolium chloride monohydrate

The title compound, C₁₈H₂₃N₂Si⁺·Cl⁻·H₂O, was synthesized from 1-[(trimethyl­sil­yl)meth­yl]benzimidazole and benzyl chloride in dimethyl­formamide. The benzimidazole ring system is approximately planar, with a maximum deviation of 0.022 (2) Å, and makes an angle of 74.80 (12)° with the phenyl ring. The crystal packing is stabilized by O—H...Cl, C—H...Cl, C—H...O and C—H...π inter­actions between symmetry-related mol­ecules together with π–π stacking inter­actions between the imidazolium and benzene rings [centroid–centroid distance = 3.5690 (15) Å] and between the benzene rings [centroid–centroid distance = 3.7223 (14) Å].

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.135
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    Si1    --  C18     ..       6.89 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Si1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          5
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              Cl
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600          5

Alert level G
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal  (x 10000)        600 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Although there are different antibacterial and antifungal drugs used in the treatment of bacterial and fungal infections, some of them have undesirable side effects. In addition, some of them become less effective due to the development of resistance to these drugs (Williams et al., 2002). Therefore, many clinically effective antibacterial and antifungal drugs have become less effective due to the development of resistance to these drugs. Since, benzimidazole compounds have been found to have a broad range of pharmacological activity, many research groups as well as our group have been interested in these type of heterocyclic compounds (Singh et al., 2000; Huang et al. 2006; Turner & Denny, 1996; Lukevics et al., 2001; Galal et al. 2009; Çetinkaya et al., 1996; Küçükbay et al., 1995, 1997, 2003, 2004, 2010; Yılmaz & Küçükbay, 2009; Tavman et al., 2005). In recent years, considerable attention has been given to the synthesis of alkylsilyl substituted benzimidazole derivatives because of their properties in cancer therapy. For example, 1-(3-trimethylsilylpropyl)benzimidazole inhibits carcinoma S-180 tumour growth in dose 1 mg.kg^-1 by 62% (on ICR mice) (Lukevics et al., 2001). These properties of silylsubstituted benzimidazole compounds, triggered us to synthesis novel trimethylsilyl substituted benzimidazole compounds. The objectives of this study were to synthesize and elucidate the crystal structure of the title compound, 1-benzyl-3-trimethylsilylmethylbenzimidazolium chloride monohydrate, (I).

In the title molecule, (Fig. 1), the benzimidazole ring system (N1/N2/C1–C7) is approximately planar, with maximum deviations of -0.022 (2) Å for C6, -0.018 (2) for C1 and 0.015 (2) for C7. The benzimidazole (N1/N2/C1–C7) and phenyl (C9–C14) systems make an angle of 74.80 (12)°. The values of the geometric parameters in (I) are comparable with those observed for other similar compounds (Akkurt et al., 2008, 2010). The average value of the Si—C bond length is 1.854 (4) Å. The angles around the Si atoms with a distorted tetrahedral geometry rang from 105.86 (16)° to 111.81 (16)°.

The crystal packing of (I) is stabilized by O—H···Cl, C—H···Cl and C—H···π interactions between symmetry-related molecules (Fig. 2 and Table 1), together with π-π stacking interactions between imidazolium and benzene (Table 2).

Related literature

For general background to benzimidazole compounds and for the biological activity of related structures, see: Galal et al. (2009); Huang et al. (2006); Küçükbay & Durmaz (1997); Küçükbay et al. (1995, 2003, 2004, 2010); Lukevics et al. (2001); Singh & Lown (2000); Tavman et al. (2005); Turner & Denny (1996); Williams et al. (2002); Yılmaz & Küçükbay (2009); Çetinkaya et al. (1996). For similar structures, see: Akkurt et al. (2008, 2010).

S2. Experimental

A mixture of 1-trimethylsilylmethylbenzimidazole (1.02 g, 5 mmol) and benzyl chloride (0.60 cm³, 5 mmol) in dimethylformamide (5 ml) was refluxed for 3 h. The mixture was then cooled and the volatiles were removed in vacuo. The residue was crystallized from a dimethylformamide/ethanol (1:1). White crystals of the title compound (1.36 g, 82%) were obtained, m.p. 425–426 K; ν_(CN) = 1553 cm^-1. Anal. Found: C 61.64, H 7.19, N 7.93%. Calculated for C₁₈H₂₅ClN₂OSi: C 61.96, H 7.22, N 8.03%. ¹H NMR (δ, DMSO-d₆): 10.21 (s, 1H, NCHN), 8.11 - 7.59 (m, 4H, C₆H₄), 7.56–7.33 (m, 5H, C₆H₅), 5.86 (s, 2H, CH₂ benzyl), 4.30 (s, 2H, CH₂Si) and 0.14 [s, 9H, (CH₃)₃Si]. ¹³C NMR (δ, DMSO-d₆): 141.6 (NCHN), 134.6, 132.1, 130.8, 129.1, 128.8 and 128.3 (C₆H₄), 126.8, 126.5, 114.3 and 113.9 (C₆H₅), 49.8 (CH₂ benzyl), 38.1(CH₂Si) and -2.5 [(CH₃)₃Si].

S3. Refinement

All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic), 0.96 Å (methyl) and 0.97 Å (methylene) with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl). H atoms of water molecule were located in difference Fourier maps and included in the subsequent refinement using restraints (O-H= 0.83 (1)Å and H···H= 1.40 (2)Å) with U_iso(H) = 1.5U_eq(O).In the last cycles of refinement, they were treated as riding on the O atoms.

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. View of the title molecule in the asymmetric unit, with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii and H bonds are shown as dashed lines.
	Fig. 2. View of the packing and hydrogen bonding interactions of (I) down the b axis. All hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

1-Benzyl-3-[(trimethylsilyl)methyl]benzimidazolium chloride monohydrate

Crystal data

C18H23N2Si^+·Cl^−·H2O	Z = 2
Mr = 348.94	F(000) = 372
Triclinic, P1	Dx = 1.203 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3592 (7) Å	Cell parameters from 28124 reflections
b = 10.9500 (9) Å	θ = 2.1–28.0°
c = 11.0522 (8) Å	µ = 0.27 mm^−1
α = 117.594 (6)°	T = 296 K
β = 103.295 (6)°	Prism, colourless
γ = 92.094 (6)°	0.57 × 0.50 × 0.36 mm
V = 963.39 (15) Å^3

Data collection

Stoe IPDS 2 diffractometer	3987 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3241 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.029
Detector resolution: 6.67 pixels mm^-1	θmax = 26.5°, θmin = 2.1°
ω scans	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→12
Tmin = 0.859, Tmax = 0.909	l = −13→13
12149 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0637P)^2 + 0.2683P] where P = (Fo^2 + 2Fc^2)/3
3987 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.32 e Å^−3
0 restraints	Δρmin = −0.32 e Å^−3

Special details

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 on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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 (Ų)

	x	y	z	Uiso*/Ueq
Si1	0.53328 (7)	0.20172 (7)	0.79168 (6)	0.05705 (19)
N1	0.72385 (17)	0.36741 (17)	0.52896 (17)	0.0466 (4)
N2	0.59349 (17)	0.36730 (17)	0.66907 (17)	0.0466 (4)
C1	0.4923 (2)	0.33506 (19)	0.54087 (19)	0.0428 (4)
C2	0.3377 (2)	0.3101 (2)	0.4971 (2)	0.0521 (5)
H2	0.2816	0.3104	0.5566	0.063*
C3	0.2721 (2)	0.2847 (2)	0.3611 (2)	0.0587 (5)
H3	0.1688	0.2667	0.3276	0.070*
C4	0.3560 (2)	0.2853 (3)	0.2717 (2)	0.0592 (5)
H4	0.3071	0.2682	0.1806	0.071*
C5	0.5084 (2)	0.3104 (2)	0.3150 (2)	0.0532 (5)
H5	0.5641	0.3111	0.2555	0.064*
C6	0.57570 (19)	0.33479 (19)	0.4512 (2)	0.0432 (4)
C7	0.7293 (2)	0.3855 (2)	0.6574 (2)	0.0505 (5)
H7	0.8165	0.4079	0.7293	0.061*
C8	0.8534 (2)	0.3833 (2)	0.4794 (2)	0.0547 (5)
H8A	0.9413	0.4273	0.5602	0.066*
H8B	0.8371	0.4442	0.4377	0.066*
C9	0.8803 (2)	0.2461 (2)	0.3720 (2)	0.0510 (5)
C10	0.8520 (3)	0.2111 (3)	0.2308 (3)	0.0717 (7)
H10	0.8171	0.2741	0.2014	0.086*
C11	0.8748 (3)	0.0831 (4)	0.1329 (3)	0.0935 (10)
H11	0.8546	0.0600	0.0377	0.112*
C12	0.9272 (3)	−0.0100 (3)	0.1753 (4)	0.0947 (10)
H12	0.9404	−0.0970	0.1089	0.114*
C13	0.9600 (3)	0.0255 (3)	0.3158 (4)	0.0909 (10)
H13	0.9980	−0.0367	0.3451	0.109*
C14	0.9372 (3)	0.1527 (3)	0.4141 (3)	0.0700 (7)
H14	0.9602	0.1760	0.5095	0.084*
C15	0.5549 (3)	0.3754 (2)	0.7947 (2)	0.0549 (5)
H15A	0.4625	0.4122	0.8003	0.066*
H15B	0.6320	0.4406	0.8796	0.066*
C16	0.3837 (3)	0.0757 (3)	0.6328 (3)	0.0812 (8)
H16A	0.4063	0.0662	0.5487	0.122*
H16B	0.2907	0.1090	0.6377	0.122*
H16C	0.3767	−0.0135	0.6297	0.122*
C17	0.4849 (4)	0.2374 (4)	0.9569 (3)	0.1001 (10)
H17A	0.4744	0.1524	0.9619	0.150*
H17B	0.3928	0.2732	0.9569	0.150*
H17C	0.5624	0.3050	1.0376	0.150*
C18	0.7121 (3)	0.1391 (3)	0.7877 (3)	0.0899 (9)
H18A	0.7028	0.0478	0.7796	0.135*
H18B	0.7869	0.2023	0.8737	0.135*
H18C	0.7403	0.1344	0.7076	0.135*
O1	0.9113 (3)	0.6314 (2)	0.9603 (2)	0.1024 (7)
H1A	0.9910	0.6000	0.9420	0.154*
H1B	0.9090	0.6350	1.0380	0.154*
Cl1	1.14370 (9)	0.44812 (10)	0.80296 (8)	0.0961 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0616 (4)	0.0668 (4)	0.0477 (3)	0.0106 (3)	0.0191 (3)	0.0301 (3)
N1	0.0349 (8)	0.0565 (9)	0.0533 (9)	0.0048 (7)	0.0145 (7)	0.0295 (8)
N2	0.0448 (9)	0.0524 (9)	0.0460 (8)	0.0074 (7)	0.0162 (7)	0.0251 (7)
C1	0.0401 (9)	0.0458 (9)	0.0466 (9)	0.0086 (7)	0.0162 (8)	0.0238 (8)
C2	0.0404 (10)	0.0611 (12)	0.0632 (12)	0.0110 (9)	0.0240 (9)	0.0324 (10)
C3	0.0358 (10)	0.0717 (14)	0.0673 (13)	0.0081 (9)	0.0120 (9)	0.0339 (11)
C4	0.0471 (12)	0.0770 (14)	0.0527 (11)	0.0088 (10)	0.0087 (9)	0.0333 (11)
C5	0.0486 (11)	0.0686 (13)	0.0516 (11)	0.0106 (9)	0.0193 (9)	0.0340 (10)
C6	0.0343 (9)	0.0484 (10)	0.0507 (10)	0.0068 (7)	0.0145 (8)	0.0260 (8)
C7	0.0418 (10)	0.0554 (11)	0.0511 (11)	0.0031 (8)	0.0079 (8)	0.0260 (9)
C8	0.0360 (10)	0.0667 (13)	0.0736 (13)	0.0050 (9)	0.0216 (9)	0.0412 (11)
C9	0.0311 (9)	0.0671 (12)	0.0673 (12)	0.0090 (8)	0.0197 (9)	0.0400 (10)
C10	0.0529 (13)	0.1023 (19)	0.0737 (15)	0.0312 (13)	0.0236 (12)	0.0498 (15)
C11	0.0647 (17)	0.126 (3)	0.0702 (17)	0.0308 (17)	0.0212 (14)	0.0299 (17)
C12	0.0684 (18)	0.0793 (19)	0.120 (3)	0.0195 (15)	0.0432 (18)	0.0266 (18)
C13	0.087 (2)	0.088 (2)	0.146 (3)	0.0402 (16)	0.069 (2)	0.077 (2)
C14	0.0671 (15)	0.0864 (17)	0.0943 (18)	0.0279 (13)	0.0444 (14)	0.0631 (15)
C15	0.0599 (12)	0.0622 (12)	0.0420 (10)	0.0129 (10)	0.0203 (9)	0.0217 (9)
C16	0.0781 (18)	0.0771 (17)	0.0790 (17)	−0.0077 (13)	0.0151 (14)	0.0347 (14)
C17	0.142 (3)	0.111 (2)	0.0703 (17)	0.022 (2)	0.0513 (19)	0.0526 (17)
C18	0.0818 (19)	0.093 (2)	0.088 (2)	0.0247 (16)	0.0135 (16)	0.0423 (17)
O1	0.1114 (17)	0.0974 (15)	0.0822 (13)	0.0288 (13)	0.0144 (12)	0.0355 (12)
Cl1	0.0818 (5)	0.1278 (7)	0.0780 (5)	0.0348 (4)	0.0259 (4)	0.0465 (4)

Geometric parameters (Å, º)

Si1—C18	1.834 (3)	C9—C10	1.378 (3)
Si1—C17	1.850 (3)	C9—C14	1.383 (3)
Si1—C16	1.852 (3)	C10—C11	1.380 (4)
Si1—C15	1.890 (2)	C10—H10	0.9300
N1—C7	1.328 (3)	C11—C12	1.368 (5)
N1—C6	1.386 (2)	C11—H11	0.9300
N1—C8	1.476 (2)	C12—C13	1.367 (5)
N2—C7	1.324 (2)	C12—H12	0.9300
N2—C1	1.387 (2)	C13—C14	1.376 (4)
N2—C15	1.478 (2)	C13—H13	0.9300
C1—C2	1.389 (3)	C14—H14	0.9300
C1—C6	1.394 (2)	C15—H15A	0.9700
C2—C3	1.374 (3)	C15—H15B	0.9700
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.398 (3)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.369 (3)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.384 (3)	C17—H17C	0.9600
C5—H5	0.9300	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—C9	1.497 (3)	C18—H18C	0.9600
C8—H8A	0.9700	O1—H1A	0.8598
C8—H8B	0.9700	O1—H1B	0.8466
C18—Si1—C17	111.82 (16)	C14—C9—C8	120.0 (2)
C18—Si1—C16	110.58 (15)	C9—C10—C11	120.5 (3)
C17—Si1—C16	110.93 (16)	C9—C10—H10	119.8
C18—Si1—C15	107.44 (14)	C11—C10—H10	119.8
C17—Si1—C15	105.86 (13)	C12—C11—C10	120.2 (3)
C16—Si1—C15	110.04 (12)	C12—C11—H11	119.9
C7—N1—C6	108.20 (15)	C10—C11—H11	119.9
C7—N1—C8	125.70 (17)	C13—C12—C11	119.7 (3)
C6—N1—C8	126.08 (16)	C13—C12—H12	120.1
C7—N2—C1	108.16 (15)	C11—C12—H12	120.1
C7—N2—C15	126.39 (17)	C12—C13—C14	120.4 (3)
C1—N2—C15	125.43 (16)	C12—C13—H13	119.8
N2—C1—C2	131.97 (17)	C14—C13—H13	119.8
N2—C1—C6	106.56 (16)	C13—C14—C9	120.4 (3)
C2—C1—C6	121.45 (18)	C13—C14—H14	119.8
C3—C2—C1	116.40 (18)	C9—C14—H14	119.8
C3—C2—H2	121.8	N2—C15—Si1	113.64 (13)
C1—C2—H2	121.8	N2—C15—H15A	108.8
C2—C3—C4	122.03 (19)	Si1—C15—H15A	108.8
C2—C3—H3	119.0	N2—C15—H15B	108.8
C4—C3—H3	119.0	Si1—C15—H15B	108.8
C5—C4—C3	121.6 (2)	H15A—C15—H15B	107.7
C5—C4—H4	119.2	Si1—C16—H16A	109.5
C3—C4—H4	119.2	Si1—C16—H16B	109.5
C4—C5—C6	116.92 (18)	H16A—C16—H16B	109.5
C4—C5—H5	121.5	Si1—C16—H16C	109.5
C6—C5—H5	121.5	H16A—C16—H16C	109.5
C5—C6—N1	131.92 (17)	H16B—C16—H16C	109.5
C5—C6—C1	121.62 (17)	Si1—C17—H17A	109.5
N1—C6—C1	106.41 (16)	Si1—C17—H17B	109.5
N2—C7—N1	110.68 (17)	H17A—C17—H17B	109.5
N2—C7—H7	124.7	Si1—C17—H17C	109.5
N1—C7—H7	124.7	H17A—C17—H17C	109.5
N1—C8—C9	112.22 (16)	H17B—C17—H17C	109.5
N1—C8—H8A	109.2	Si1—C18—H18A	109.5
C9—C8—H8A	109.2	Si1—C18—H18B	109.5
N1—C8—H8B	109.2	H18A—C18—H18B	109.5
C9—C8—H8B	109.2	Si1—C18—H18C	109.5
H8A—C8—H8B	107.9	H18A—C18—H18C	109.5
C10—C9—C14	118.7 (2)	H18B—C18—H18C	109.5
C10—C9—C8	121.3 (2)	H1A—O1—H1B	107.0
C7—N2—C1—C2	−178.0 (2)	C15—N2—C7—N1	178.44 (17)
C15—N2—C1—C2	3.6 (3)	C6—N1—C7—N2	−0.3 (2)
C7—N2—C1—C6	0.1 (2)	C8—N1—C7—N2	178.18 (18)
C15—N2—C1—C6	−178.27 (17)	C7—N1—C8—C9	109.6 (2)
N2—C1—C2—C3	178.1 (2)	C6—N1—C8—C9	−72.2 (2)
C6—C1—C2—C3	0.2 (3)	N1—C8—C9—C10	108.7 (2)
C1—C2—C3—C4	−0.6 (3)	N1—C8—C9—C14	−72.5 (2)
C2—C3—C4—C5	0.4 (4)	C14—C9—C10—C11	2.3 (4)
C3—C4—C5—C6	0.2 (3)	C8—C9—C10—C11	−178.8 (2)
C4—C5—C6—N1	−177.7 (2)	C9—C10—C11—C12	−0.5 (4)
C4—C5—C6—C1	−0.6 (3)	C10—C11—C12—C13	−1.5 (5)
C7—N1—C6—C5	177.7 (2)	C11—C12—C13—C14	1.7 (5)
C8—N1—C6—C5	−0.7 (3)	C12—C13—C14—C9	0.2 (4)
C7—N1—C6—C1	0.3 (2)	C10—C9—C14—C13	−2.2 (3)
C8—N1—C6—C1	−178.13 (17)	C8—C9—C14—C13	179.0 (2)
N2—C1—C6—C5	−177.97 (18)	C7—N2—C15—Si1	−91.7 (2)
C2—C1—C6—C5	0.4 (3)	C1—N2—C15—Si1	86.4 (2)
N2—C1—C6—N1	−0.2 (2)	C18—Si1—C15—N2	60.61 (19)
C2—C1—C6—N1	178.10 (18)	C17—Si1—C15—N2	−179.77 (18)
C1—N2—C7—N1	0.1 (2)	C16—Si1—C15—N2	−59.84 (19)

Hydrogen-bond geometry (Å, º)

Cg3 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl1	0.86	2.45	3.257 (2)	157
O1—H1B···Cl1^i	0.85	2.45	3.250 (3)	158
C7—H7···O1	0.93	2.51	3.170 (3)	128
C8—H8A···Cl1	0.97	2.81	3.703 (2)	153
C3—H3···Cg3^ii	0.93	2.69	3.526 (2)	151

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) x−1, y, z.