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Acta Crystallogr Sect E Struct Rep Online. 2012 January 1; 68(Pt 1): o59.
Published online 2011 December 10. doi:  10.1107/S1600536811052408
PMCID: PMC3254415

Ethyl 2-(4-nitro­phen­yl)-1-[3-(2-oxopyrrolidin-1-yl)prop­yl]-1H-benzimidazole-5-carboxyl­ate

Abstract

In the title compound, C23H24N4O5, the essentially planar benzimidazole ring system [maximum deviation = 0.008 (2) Å] forms a dihedral angle of 39.22 (7)° with the attached nitro­benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with a C atom as the flap. In the crystal, mol­ecules are connected by C—H(...)O inter­actions, forming sheets propagating in (011). The crystal packing also features weak π–π stacking inter­actions [centroid–centroid = 3.6746 (12) Å].

Related literature

For applications of benzimidazole compounds, see: Rao et al. (2002 [triangle]); Ali et al. (2007 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]). For ring conformations, see: Cremer & Pople (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-68-00o59-scheme1.jpg

Experimental

Crystal data

  • C23H24N4O5
  • M r = 436.46
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-00o59-efi1.jpg
  • a = 9.3125 (1) Å
  • b = 10.0941 (1) Å
  • c = 12.9955 (2) Å
  • α = 91.958 (1)°
  • β = 107.752 (1)°
  • γ = 114.465 (1)°
  • V = 1040.67 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 K
  • 0.34 × 0.20 × 0.13 mm

Data collection

  • Bruker SMART APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.967, T max = 0.987
  • 27734 measured reflections
  • 7466 independent reflections
  • 5375 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.069
  • wR(F 2) = 0.197
  • S = 1.04
  • 7466 reflections
  • 289 parameters
  • H-atom parameters constrained
  • Δρmax = 0.50 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811052408/hb6545sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052408/hb6545Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052408/hb6545Isup3.cml

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia for the Research University Grant (Nos. 1001/PFIZIK/811151 and 1001/PSK/8620012). The authors also wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Mol­ecular Medicine, Universiti of Sains Malaysia.

supplementary crystallographic information

Comment

Benzimidazole derivatives have many clinical applications (Rao et al., 2002) and are being currently evaluated for their anti-TB activities (Ali et al., 2007).

In the title compound, (I), Fig. 1, the benzimidazole (N1–N2/C1–C7) ring is essentially planar with maximum deviation of 0.008 (2) for atom C3. This ring also makes dihedral angles of 77.02 (11) and 39.22 (7)° with the mean plane of pyrrolidin-2-one, (O3/N3/C20–C23) and nitrobenzene, (C8–C13) groups, respectively. The mean plane of pyrrolidin-2-one, (O3/N3/C20–C23) adopts an envelope conformation with puckering parameters Q = 0.237 (3) Å and [var phi] = 76.0 (6)° (Cremer & Pople, 1975).

In the crystal (Fig. 2), the molecules are connected by C15—H15A···O3, C15—H15B···O3 and C19—H19A···O2 interactions to form (011) sheets. π–π stacking interactions are observed between the benzene (C1–C6; centroid Cg3) rings with their centroids distance of 3.6746 (12) Å [symmetry code : -x,-y,1-z].

Experimental

Ethyl 3-amino-4-(3(2-oxopyrrolidin-1yl)propylamino)benzoate (0.84 mmol) and sodium metabisulfite adduct of 4-nitrobenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 130 °C for 2 hrs. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na2SO4 and the evaporated in vacuo to yield the product. The product was recrystallised from ethyl acetate as orange blocks.

Refinement

All the H atoms were positioned geometrically and refined using a riding model with with C–H = 0.95–0.99 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms.

Figures

Fig. 1.
The structure of the title compound, showing 50% probability displacement ellipsoids.
Fig. 2.
The crystal packing, viewed along the a-axis, showing two-dimensional planes parallel to (011). Hydrogen atoms that not involved in hydrogen bonding (dashed lines) are omitted for clarity.

Crystal data

C23H24N4O5Z = 2
Mr = 436.46F(000) = 460
Triclinic, P1Dx = 1.393 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3125 (1) ÅCell parameters from 8871 reflections
b = 10.0941 (1) Åθ = 2.5–32.6°
c = 12.9955 (2) ŵ = 0.10 mm1
α = 91.958 (1)°T = 100 K
β = 107.752 (1)°Block, orange
γ = 114.465 (1)°0.34 × 0.20 × 0.13 mm
V = 1040.67 (2) Å3

Data collection

Bruker SMART APEXII CCD diffractometer7466 independent reflections
Radiation source: fine-focus sealed tube5375 reflections with I > 2σ(I)
graphiteRint = 0.032
[var phi] and ω scansθmax = 32.6°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −14→14
Tmin = 0.967, Tmax = 0.987k = −15→15
27734 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0843P)2 + 0.8488P] where P = (Fo2 + 2Fc2)/3
7466 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = −0.30 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O1−0.29047 (16)−0.18231 (15)0.17443 (11)0.0271 (3)
O2−0.45664 (18)−0.31986 (16)0.26240 (12)0.0328 (3)
O30.2053 (2)0.51173 (19)0.95685 (13)0.0385 (4)
O40.82578 (18)0.95186 (18)0.77738 (14)0.0371 (4)
O50.6533 (2)1.04206 (17)0.78208 (14)0.0388 (4)
N10.11744 (17)0.29815 (16)0.46007 (12)0.0201 (3)
N20.00661 (17)0.29678 (16)0.59278 (11)0.0193 (3)
N3−0.0066 (2)0.56743 (18)0.86162 (13)0.0245 (3)
N40.6825 (2)0.93979 (18)0.75733 (13)0.0268 (3)
C1−0.0276 (2)0.16584 (19)0.43862 (14)0.0189 (3)
C2−0.1050 (2)0.04589 (19)0.35168 (14)0.0201 (3)
H2A−0.05860.04550.29590.024*
C3−0.2518 (2)−0.07262 (19)0.34957 (14)0.0208 (3)
C4−0.3197 (2)−0.0732 (2)0.43315 (15)0.0233 (3)
H4A−0.4194−0.15700.42990.028*
C5−0.2451 (2)0.0444 (2)0.51921 (14)0.0224 (3)
H5A−0.29140.04430.57510.027*
C6−0.0981 (2)0.16403 (19)0.52027 (14)0.0194 (3)
C70.1333 (2)0.37277 (18)0.55203 (14)0.0185 (3)
C80.2713 (2)0.52054 (19)0.60439 (13)0.0193 (3)
C90.2460 (2)0.6325 (2)0.65125 (14)0.0217 (3)
H9A0.13660.61350.65000.026*
C100.3803 (2)0.7712 (2)0.69957 (14)0.0221 (3)
H10A0.36380.84780.73100.026*
C110.5388 (2)0.79566 (19)0.70104 (14)0.0216 (3)
C120.5674 (2)0.6891 (2)0.65223 (15)0.0237 (3)
H12A0.67640.71000.65170.028*
C130.4322 (2)0.5512 (2)0.60426 (14)0.0221 (3)
H13A0.44910.47630.57080.027*
C14−0.3446 (2)−0.2050 (2)0.25940 (15)0.0234 (3)
C15−0.3754 (2)−0.3076 (2)0.08290 (16)0.0292 (4)
H15A−0.4990−0.35010.06360.035*
H15B−0.3399−0.38590.10320.035*
C16−0.3270 (3)−0.2504 (3)−0.01223 (19)0.0441 (6)
H16A−0.3815−0.3318−0.07540.066*
H16B−0.2044−0.20860.00800.066*
H16C−0.3632−0.1734−0.03160.066*
C17−0.0017 (2)0.3308 (2)0.70099 (13)0.0214 (3)
H17A0.10630.41510.74670.026*
H17B−0.01490.24420.73760.026*
C18−0.1456 (2)0.3693 (2)0.69594 (14)0.0236 (3)
H18A−0.25480.28190.65740.028*
H18B−0.13920.45030.65400.028*
C19−0.1347 (2)0.4175 (2)0.81236 (15)0.0261 (4)
H19A−0.24530.40990.80950.031*
H19B−0.10990.34900.85940.031*
C20−0.0400 (3)0.6949 (2)0.84211 (18)0.0354 (5)
H20A−0.14780.67900.85050.042*
H20B−0.04390.71530.76760.042*
C210.1094 (4)0.8213 (3)0.9307 (2)0.0443 (6)
H21A0.14670.91440.90170.053*
H21B0.07930.83790.99520.053*
C220.2468 (3)0.7692 (2)0.96175 (18)0.0353 (5)
H22A0.32480.81020.92100.042*
H22B0.31210.79961.04160.042*
C230.1509 (2)0.6021 (2)0.92917 (15)0.0268 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0245 (6)0.0248 (7)0.0246 (6)0.0055 (5)0.0078 (5)−0.0053 (5)
O20.0311 (7)0.0247 (7)0.0282 (7)0.0022 (6)0.0062 (6)0.0020 (6)
O30.0361 (8)0.0421 (9)0.0348 (8)0.0228 (7)0.0031 (6)−0.0081 (7)
O40.0244 (7)0.0338 (8)0.0417 (9)0.0048 (6)0.0088 (6)0.0019 (7)
O50.0404 (8)0.0261 (8)0.0417 (9)0.0100 (7)0.0116 (7)−0.0034 (6)
N10.0184 (6)0.0202 (7)0.0214 (7)0.0080 (5)0.0073 (5)0.0017 (5)
N20.0188 (6)0.0213 (7)0.0165 (6)0.0072 (5)0.0070 (5)0.0028 (5)
N30.0271 (7)0.0251 (8)0.0226 (7)0.0122 (6)0.0097 (6)0.0024 (6)
N40.0276 (7)0.0226 (8)0.0231 (7)0.0048 (6)0.0089 (6)0.0020 (6)
C10.0173 (7)0.0202 (8)0.0204 (7)0.0086 (6)0.0079 (6)0.0034 (6)
C20.0194 (7)0.0206 (8)0.0200 (7)0.0089 (6)0.0068 (6)0.0019 (6)
C30.0193 (7)0.0205 (8)0.0204 (7)0.0079 (6)0.0053 (6)0.0028 (6)
C40.0199 (7)0.0222 (8)0.0240 (8)0.0058 (6)0.0078 (6)0.0064 (6)
C50.0221 (7)0.0228 (8)0.0205 (7)0.0069 (7)0.0092 (6)0.0048 (6)
C60.0188 (7)0.0199 (8)0.0178 (7)0.0078 (6)0.0055 (6)0.0025 (6)
C70.0181 (7)0.0177 (7)0.0194 (7)0.0078 (6)0.0064 (6)0.0028 (6)
C80.0195 (7)0.0204 (8)0.0174 (7)0.0086 (6)0.0063 (6)0.0033 (6)
C90.0202 (7)0.0230 (8)0.0232 (8)0.0105 (7)0.0080 (6)0.0037 (6)
C100.0264 (8)0.0190 (8)0.0207 (8)0.0103 (7)0.0080 (6)0.0027 (6)
C110.0222 (7)0.0194 (8)0.0184 (7)0.0051 (6)0.0066 (6)0.0028 (6)
C120.0200 (7)0.0245 (9)0.0241 (8)0.0067 (7)0.0093 (6)0.0031 (7)
C130.0226 (8)0.0240 (8)0.0215 (8)0.0104 (7)0.0101 (6)0.0031 (6)
C140.0208 (7)0.0236 (8)0.0225 (8)0.0098 (7)0.0036 (6)0.0029 (6)
C150.0267 (9)0.0276 (10)0.0255 (9)0.0091 (8)0.0046 (7)−0.0052 (7)
C160.0467 (13)0.0415 (13)0.0320 (11)0.0082 (11)0.0157 (10)−0.0058 (10)
C170.0224 (7)0.0263 (9)0.0149 (7)0.0103 (7)0.0067 (6)0.0033 (6)
C180.0196 (7)0.0285 (9)0.0202 (8)0.0084 (7)0.0072 (6)−0.0003 (7)
C190.0234 (8)0.0301 (9)0.0238 (8)0.0088 (7)0.0119 (7)0.0000 (7)
C200.0498 (12)0.0293 (10)0.0289 (10)0.0226 (10)0.0095 (9)0.0032 (8)
C210.0650 (16)0.0292 (11)0.0329 (11)0.0212 (11)0.0094 (11)0.0030 (9)
C220.0365 (10)0.0305 (10)0.0285 (10)0.0038 (9)0.0143 (8)−0.0019 (8)
C230.0284 (9)0.0302 (10)0.0216 (8)0.0116 (8)0.0114 (7)−0.0017 (7)

Geometric parameters (Å, °)

O1—C141.337 (2)C10—C111.386 (2)
O1—C151.461 (2)C10—H10A0.9500
O2—C141.208 (2)C11—C121.387 (3)
O3—C231.229 (3)C12—C131.386 (3)
O4—N41.231 (2)C12—H12A0.9500
O5—N41.227 (2)C13—H13A0.9500
N1—C71.325 (2)C15—C161.496 (3)
N1—C11.392 (2)C15—H15A0.9900
N2—C61.380 (2)C15—H15B0.9900
N2—C71.386 (2)C16—H16A0.9800
N2—C171.468 (2)C16—H16B0.9800
N3—C231.347 (2)C16—H16C0.9800
N3—C191.448 (2)C17—C181.527 (2)
N3—C201.456 (3)C17—H17A0.9900
N4—C111.470 (2)C17—H17B0.9900
C1—C21.396 (2)C18—C191.534 (2)
C1—C61.405 (2)C18—H18A0.9900
C2—C31.386 (2)C18—H18B0.9900
C2—H2A0.9500C19—H19A0.9900
C3—C41.413 (2)C19—H19B0.9900
C3—C141.492 (2)C20—C211.531 (3)
C4—C51.377 (3)C20—H20A0.9900
C4—H4A0.9500C20—H20B0.9900
C5—C61.396 (2)C21—C221.527 (4)
C5—H5A0.9500C21—H21A0.9900
C7—C81.466 (2)C21—H21B0.9900
C8—C131.400 (2)C22—C231.515 (3)
C8—C91.402 (2)C22—H22A0.9900
C9—C101.389 (3)C22—H22B0.9900
C9—H9A0.9500
C14—O1—C15115.53 (15)O1—C14—C3112.44 (15)
C7—N1—C1104.74 (14)O1—C15—C16107.13 (17)
C6—N2—C7106.18 (13)O1—C15—H15A110.3
C6—N2—C17124.31 (14)C16—C15—H15A110.3
C7—N2—C17128.43 (14)O1—C15—H15B110.3
C23—N3—C19123.98 (17)C16—C15—H15B110.3
C23—N3—C20114.20 (17)H15A—C15—H15B108.5
C19—N3—C20121.81 (16)C15—C16—H16A109.5
O5—N4—O4123.33 (17)C15—C16—H16B109.5
O5—N4—C11118.19 (16)H16A—C16—H16B109.5
O4—N4—C11118.48 (16)C15—C16—H16C109.5
N1—C1—C2129.65 (15)H16A—C16—H16C109.5
N1—C1—C6110.09 (15)H16B—C16—H16C109.5
C2—C1—C6120.25 (16)N2—C17—C18113.73 (14)
C3—C2—C1117.63 (16)N2—C17—H17A108.8
C3—C2—H2A121.2C18—C17—H17A108.8
C1—C2—H2A121.2N2—C17—H17B108.8
C2—C3—C4121.30 (16)C18—C17—H17B108.8
C2—C3—C14121.58 (16)H17A—C17—H17B107.7
C4—C3—C14117.12 (16)C17—C18—C19110.22 (14)
C5—C4—C3121.73 (16)C17—C18—H18A109.6
C5—C4—H4A119.1C19—C18—H18A109.6
C3—C4—H4A119.1C17—C18—H18B109.6
C4—C5—C6116.66 (16)C19—C18—H18B109.6
C4—C5—H5A121.7H18A—C18—H18B108.1
C6—C5—H5A121.7N3—C19—C18112.88 (15)
N2—C6—C5131.67 (16)N3—C19—H19A109.0
N2—C6—C1105.92 (14)C18—C19—H19A109.0
C5—C6—C1122.42 (16)N3—C19—H19B109.0
N1—C7—N2113.07 (15)C18—C19—H19B109.0
N1—C7—C8122.98 (15)H19A—C19—H19B107.8
N2—C7—C8123.96 (15)N3—C20—C21103.43 (18)
C13—C8—C9119.31 (16)N3—C20—H20A111.1
C13—C8—C7118.47 (15)C21—C20—H20A111.1
C9—C8—C7122.19 (15)N3—C20—H20B111.1
C10—C9—C8120.27 (15)C21—C20—H20B111.1
C10—C9—H9A119.9H20A—C20—H20B109.0
C8—C9—H9A119.9C22—C21—C20104.44 (18)
C11—C10—C9118.67 (16)C22—C21—H21A110.9
C11—C10—H10A120.7C20—C21—H21A110.9
C9—C10—H10A120.7C22—C21—H21B110.9
C10—C11—C12122.60 (16)C20—C21—H21B110.9
C10—C11—N4118.71 (16)H21A—C21—H21B108.9
C12—C11—N4118.68 (16)C23—C22—C21104.12 (18)
C13—C12—C11118.05 (16)C23—C22—H22A110.9
C13—C12—H12A121.0C21—C22—H22A110.9
C11—C12—H12A121.0C23—C22—H22B110.9
C12—C13—C8121.02 (16)C21—C22—H22B110.9
C12—C13—H13A119.5H22A—C22—H22B109.0
C8—C13—H13A119.5O3—C23—N3124.88 (19)
O2—C14—O1123.64 (17)O3—C23—C22127.05 (19)
O2—C14—C3123.92 (17)N3—C23—C22108.06 (18)
C7—N1—C1—C2179.48 (17)C9—C10—C11—N4−176.78 (16)
C7—N1—C1—C60.23 (19)O5—N4—C11—C10−13.9 (3)
N1—C1—C2—C3−179.08 (17)O4—N4—C11—C10166.00 (17)
C6—C1—C2—C30.1 (2)O5—N4—C11—C12166.58 (18)
C1—C2—C3—C4−0.9 (3)O4—N4—C11—C12−13.5 (3)
C1—C2—C3—C14179.30 (15)C10—C11—C12—C13−2.7 (3)
C2—C3—C4—C51.2 (3)N4—C11—C12—C13176.81 (16)
C14—C3—C4—C5−179.04 (16)C11—C12—C13—C80.4 (3)
C3—C4—C5—C6−0.5 (3)C9—C8—C13—C121.7 (3)
C7—N2—C6—C5−179.83 (18)C7—C8—C13—C12179.80 (16)
C17—N2—C6—C511.2 (3)C15—O1—C14—O2−0.5 (3)
C7—N2—C6—C10.53 (18)C15—O1—C14—C3179.81 (15)
C17—N2—C6—C1−168.39 (15)C2—C3—C14—O2167.84 (18)
C4—C5—C6—N2−179.88 (17)C4—C3—C14—O2−12.0 (3)
C4—C5—C6—C1−0.3 (3)C2—C3—C14—O1−12.4 (2)
N1—C1—C6—N2−0.49 (19)C4—C3—C14—O1167.77 (15)
C2—C1—C6—N2−179.81 (15)C14—O1—C15—C16167.07 (17)
N1—C1—C6—C5179.83 (16)C6—N2—C17—C18−77.5 (2)
C2—C1—C6—C50.5 (3)C7—N2—C17—C18116.10 (19)
C1—N1—C7—N20.12 (19)N2—C17—C18—C19−174.58 (15)
C1—N1—C7—C8−179.84 (15)C23—N3—C19—C18−95.5 (2)
C6—N2—C7—N1−0.42 (19)C20—N3—C19—C1885.1 (2)
C17—N2—C7—N1167.89 (16)C17—C18—C19—N377.3 (2)
C6—N2—C7—C8179.53 (15)C23—N3—C20—C21−13.5 (2)
C17—N2—C7—C8−12.2 (3)C19—N3—C20—C21165.93 (18)
N1—C7—C8—C13−38.3 (2)N3—C20—C21—C2222.3 (2)
N2—C7—C8—C13141.76 (17)C20—C21—C22—C23−23.2 (2)
N1—C7—C8—C9139.76 (18)C19—N3—C23—O30.2 (3)
N2—C7—C8—C9−40.2 (2)C20—N3—C23—O3179.69 (19)
C13—C8—C9—C10−1.7 (3)C19—N3—C23—C22179.15 (16)
C7—C8—C9—C10−179.69 (16)C20—N3—C23—C22−1.4 (2)
C8—C9—C10—C11−0.5 (3)C21—C22—C23—O3−165.3 (2)
C9—C10—C11—C122.7 (3)C21—C22—C23—N315.8 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C15—H15A···O3i0.992.413.355 (3)159
C15—H15B···O3ii0.992.383.186 (3)139
C19—H19A···O2iii0.992.383.312 (3)156

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6545).

References

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