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Acta Crystallogr Sect E Struct Rep Online. 2012 September 1; 68(Pt 9): o2715–o2716.
Published online 2012 August 15. doi:  10.1107/S1600536812034903
PMCID: PMC3435731

Ethyl 1-phenyl-2-[4-(trifluoro­meth­oxy)phen­yl]-1H-benzimidazole-5-carboxyl­ate

Abstract

In the title compound, C23H17F3N2O3, an intra­molecular C—H(...)F hydrogen bond generates an S(6) ring motif. The essentially planar 1H-benzimidazole ring system [maximum deviation = 0.021 (2) Å] forms dihedral angles of 25.00 (10) and 62.53 (11)° with the trifluoro­meth­oxy-substituted benzene and phenyl rings, respectively. The twist of the ethyl acetate group from the least-squares plane of the 1H-benzimidazole ring system is defined by a C(=O)—O—C—C torsion angle of 79.5 (3)°. In the crystal, mol­ecules are linked into a two-dimensional network parallel to the bc plane by weak C—H(...)N and C—H(...)O hydrogen bonds. Weak C—H(...)π inter­actions also observed.

Related literature  

For the biological activity of benzimidazoles, see: Lemura et al. (1986 [triangle]); Zhang et al. (2008 [triangle]). For related structures, see: Yoon et al. (2011 [triangle], 2012a [triangle],b [triangle],c [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-68-o2715-scheme1.jpg

Experimental  

Crystal data  

  • C23H17F3N2O3
  • M r = 426.39
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o2715-efi1.jpg
  • a = 8.0204 (4) Å
  • b = 10.8943 (6) Å
  • c = 11.4329 (7) Å
  • α = 76.706 (4)°
  • β = 83.269 (4)°
  • γ = 81.227 (4)°
  • V = 957.31 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 100 K
  • 0.37 × 0.27 × 0.20 mm

Data collection  

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.957, T max = 0.977
  • 12437 measured reflections
  • 4388 independent reflections
  • 3028 reflections with I > 2σ(I)
  • R int = 0.065

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.075
  • wR(F 2) = 0.206
  • S = 1.05
  • 4388 reflections
  • 281 parameters
  • H-atom parameters constrained
  • Δρmax = 0.87 e Å−3
  • Δρmin = −0.42 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/S1600536812034903/lh5511sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034903/lh5511Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034903/lh5511Isup3.cml

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

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University grants Nos.1001/PFIZIK/811151 and 1001/PSK/8620012. The authors also wish to express their thanks to Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Mol­ecular Medicine, Universiti Sains Malaysia. SA thanks the Malaysian Government and USM for an Academic Staff Training Scheme fellowship (ASTS).

supplementary crystallographic information

Comment

Benzimidazole-based heterocycles are of wide interest because of their diverse biological activities and various clinical applications. Among various applications, they are known to exhibit antihistamine (Lemura et al., 1986) and immunosuppressive (Zhang et al., 2008) activities. As part of our ongoing structural studies of benzimidazole derivatives (Yoon et al., 2011), we report the structure of the title compound.

The molecular structure is shown in Fig. 1. Bond lengths and angles are within normal ranges and are comparable to related structures (Yoon et al., 2012a,b,c). An intramolecular C12—H12A···F2 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The essentially planar 1H-benzimidazole ring system [N1/N2/C1–C7, with a maximum deviation of 0.021 (2) Å at atoms C6 and C7] is inclined to the trifluoromethoxy-substituted benzene ring (C8–C13) and the pendant phenyl ring (C14–C19), making dihedral angles of 25.00 (10) and 62.53 (11)°, respectively. The ethyl acetate group (O1/O2/C20–C22) is twisted away from the least-square plane of the 1H-benzimidazole ring at the O1–C21 bond, as indicated by the torsion angle C20—O1—C21—C22 = 79.5 (3)°.

The crystal packing is shown in Fig. 2. Weak intermolecular C15—H15A···N1i, C18—H18A···O2ii and C19—H19A···O2iii (Table 1) hydrogen bonds link the molecules into a two-dimensional network parallel to the bc-plane. The crystal structure is further stabilized by weak intermolecular C13—H13A···Cg1 and C21—H21A···Cg2 (Table 1) interactions (Cg1 and Cg2 are the centroids of C14–C19 and N1/N2/C1/C6/C7 rings, respectively).

Experimental

Ethyl 3-amino-4-(phenyl amino) benzoate (0.84 mmol) and the sodium metabisulfite adduct of trifluoromethoxy benzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was refluxed at 403K for 2 h. 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. Crystals were obtained from a solution of the title compound in ethyl acetate.

Refinement

All H atoms were positioned geometrically [C–H = 0.95–0.99 Å] and refined using a riding model with Uiso(H) = 1.2 Ueq(C) or Uiso(H) = 1.5 Ueq(Cmethyl). A rotating group model was applied to the methyl group hydrogen atoms.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids. The dashed line indicates a weak hydrogen bond.
Fig. 2.
The crystal packing of the title compound viewed along the c-axis. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C23H17F3N2O3Z = 2
Mr = 426.39F(000) = 440
Triclinic, P1Dx = 1.479 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0204 (4) ÅCell parameters from 2463 reflections
b = 10.8943 (6) Åθ = 2.6–29.7°
c = 11.4329 (7) ŵ = 0.12 mm1
α = 76.706 (4)°T = 100 K
β = 83.269 (4)°Block, colourless
γ = 81.227 (4)°0.37 × 0.27 × 0.20 mm
V = 957.31 (9) Å3

Data collection

Bruker SMART APEXII CCD area-detector diffractometer4388 independent reflections
Radiation source: fine-focus sealed tube3028 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
[var phi] and ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −10→10
Tmin = 0.957, Tmax = 0.977k = −14→14
12437 measured reflectionsl = −14→12

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)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.206H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.123P)2] where P = (Fo2 + 2Fc2)/3
4388 reflections(Δ/σ)max < 0.001
281 parametersΔρmax = 0.87 e Å3
0 restraintsΔρmin = −0.42 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 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.

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

xyzUiso*/Ueq
F10.2469 (2)1.38071 (15)0.84048 (15)0.0330 (4)
F20.3445 (2)1.20231 (16)0.94936 (15)0.0353 (5)
F30.5165 (2)1.32405 (16)0.84269 (18)0.0379 (5)
O11.3555 (2)0.41546 (17)0.33931 (16)0.0229 (4)
O21.1298 (2)0.50753 (18)0.23637 (17)0.0247 (4)
O30.3587 (2)1.23201 (19)0.74959 (18)0.0296 (5)
N10.8708 (3)0.8508 (2)0.4871 (2)0.0207 (5)
N21.0123 (3)0.8059 (2)0.65459 (19)0.0194 (5)
C11.0871 (3)0.7205 (2)0.5846 (2)0.0185 (5)
C21.2206 (3)0.6226 (2)0.6035 (2)0.0204 (6)
H2A1.28000.60480.67390.024*
C31.2633 (3)0.5524 (2)0.5155 (2)0.0202 (6)
H3A1.35360.48450.52540.024*
C41.1749 (3)0.5801 (2)0.4112 (2)0.0198 (6)
C51.0430 (3)0.6791 (2)0.3917 (2)0.0197 (5)
H5A0.98470.69770.32070.024*
C60.9991 (3)0.7504 (2)0.4805 (2)0.0192 (5)
C70.8817 (3)0.8802 (2)0.5908 (2)0.0189 (5)
C80.7550 (3)0.9748 (2)0.6377 (2)0.0191 (5)
C90.6588 (3)1.0655 (2)0.5555 (2)0.0215 (6)
H9A0.68231.06850.47160.026*
C100.5302 (3)1.1510 (3)0.5944 (2)0.0230 (6)
H10A0.46671.21290.53800.028*
C110.4958 (3)1.1445 (2)0.7171 (2)0.0217 (6)
C120.5862 (3)1.0553 (3)0.8008 (2)0.0246 (6)
H12A0.56011.05190.88460.029*
C130.7156 (3)0.9708 (3)0.7609 (2)0.0234 (6)
H13A0.77840.90930.81810.028*
C141.0648 (3)0.8116 (2)0.7687 (2)0.0192 (5)
C151.1250 (3)0.9200 (3)0.7822 (2)0.0231 (6)
H15A1.13840.98890.71510.028*
C161.1652 (4)0.9260 (3)0.8952 (3)0.0276 (6)
H16A1.20421.00030.90630.033*
C171.1488 (3)0.8242 (3)0.9922 (2)0.0273 (6)
H17A1.17550.82931.06950.033*
C181.0937 (3)0.7152 (3)0.9766 (3)0.0270 (6)
H18A1.08540.64491.04290.032*
C191.0505 (3)0.7082 (3)0.8650 (2)0.0216 (6)
H19A1.01160.63380.85420.026*
C201.2139 (3)0.5004 (2)0.3189 (2)0.0191 (5)
C211.3934 (4)0.3264 (3)0.2602 (3)0.0264 (6)
H21A1.28690.29670.24900.032*
H21B1.46910.25150.29940.032*
C221.4756 (4)0.3817 (3)0.1393 (3)0.0314 (7)
H22A1.50590.31530.09260.047*
H22B1.57810.41550.14960.047*
H22C1.39680.45040.09630.047*
C230.3683 (3)1.2831 (3)0.8431 (2)0.0243 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0296 (9)0.0283 (9)0.0357 (10)0.0098 (7)0.0045 (7)−0.0080 (7)
F20.0390 (10)0.0321 (10)0.0271 (9)0.0045 (8)0.0087 (7)−0.0028 (7)
F30.0253 (9)0.0341 (10)0.0577 (12)−0.0051 (7)0.0036 (8)−0.0194 (9)
O10.0208 (9)0.0244 (10)0.0220 (10)0.0033 (7)0.0008 (7)−0.0077 (8)
O20.0235 (10)0.0285 (11)0.0222 (10)−0.0004 (8)−0.0027 (8)−0.0071 (8)
O30.0225 (10)0.0368 (12)0.0281 (11)0.0106 (8)−0.0037 (8)−0.0125 (9)
N10.0180 (10)0.0213 (12)0.0201 (11)−0.0009 (9)0.0020 (9)−0.0022 (9)
N20.0175 (10)0.0197 (11)0.0190 (11)0.0012 (8)0.0008 (8)−0.0035 (9)
C10.0163 (12)0.0209 (13)0.0185 (13)−0.0044 (10)0.0022 (10)−0.0054 (10)
C20.0190 (12)0.0238 (14)0.0175 (13)−0.0027 (10)−0.0020 (10)−0.0026 (10)
C30.0162 (12)0.0216 (14)0.0208 (13)−0.0012 (10)0.0025 (10)−0.0033 (11)
C40.0191 (12)0.0185 (13)0.0204 (13)−0.0054 (10)0.0057 (10)−0.0034 (10)
C50.0184 (12)0.0231 (14)0.0165 (13)−0.0027 (10)−0.0011 (10)−0.0022 (10)
C60.0147 (11)0.0202 (13)0.0206 (13)−0.0012 (10)0.0032 (10)−0.0034 (10)
C70.0165 (12)0.0202 (13)0.0183 (13)−0.0034 (10)−0.0013 (10)−0.0003 (10)
C80.0172 (12)0.0185 (13)0.0213 (13)−0.0033 (10)−0.0003 (10)−0.0042 (10)
C90.0214 (13)0.0257 (14)0.0159 (13)−0.0037 (10)0.0016 (10)−0.0030 (11)
C100.0196 (13)0.0245 (14)0.0228 (14)−0.0003 (10)−0.0038 (10)−0.0016 (11)
C110.0163 (12)0.0238 (14)0.0243 (14)0.0020 (10)0.0016 (10)−0.0086 (11)
C120.0211 (13)0.0319 (16)0.0185 (13)0.0013 (11)0.0008 (10)−0.0054 (11)
C130.0213 (13)0.0242 (14)0.0211 (14)0.0010 (11)−0.0018 (10)−0.0004 (11)
C140.0143 (12)0.0242 (14)0.0172 (13)0.0028 (10)0.0005 (10)−0.0050 (10)
C150.0196 (13)0.0245 (14)0.0235 (14)−0.0021 (10)0.0030 (10)−0.0046 (11)
C160.0237 (14)0.0324 (16)0.0289 (15)−0.0056 (12)0.0002 (11)−0.0112 (13)
C170.0203 (13)0.0425 (18)0.0198 (14)0.0028 (12)−0.0029 (11)−0.0121 (12)
C180.0198 (13)0.0331 (16)0.0230 (14)0.0011 (11)0.0012 (11)−0.0001 (12)
C190.0161 (12)0.0214 (13)0.0249 (14)0.0021 (10)0.0009 (10)−0.0047 (11)
C200.0174 (12)0.0199 (13)0.0178 (13)−0.0028 (10)0.0034 (10)−0.0015 (10)
C210.0267 (14)0.0229 (15)0.0302 (15)0.0027 (11)−0.0028 (12)−0.0109 (12)
C220.0265 (15)0.0397 (18)0.0287 (16)−0.0009 (13)0.0022 (12)−0.0132 (13)
C230.0212 (13)0.0245 (14)0.0249 (14)0.0000 (10)0.0001 (11)−0.0035 (11)

Geometric parameters (Å, º)

F1—C231.326 (3)C9—C101.385 (4)
F2—C231.339 (3)C9—H9A0.9500
F3—C231.331 (3)C10—C111.385 (4)
O1—C201.357 (3)C10—H10A0.9500
O1—C211.449 (3)C11—C121.380 (4)
O2—C201.205 (3)C12—C131.386 (4)
O3—C231.328 (3)C12—H12A0.9500
O3—C111.416 (3)C13—H13A0.9500
N1—C71.314 (3)C14—C151.388 (4)
N1—C61.392 (3)C14—C191.390 (4)
N2—C11.388 (3)C15—C161.386 (4)
N2—C71.390 (3)C15—H15A0.9500
N2—C141.434 (3)C16—C171.386 (4)
C1—C21.389 (4)C16—H16A0.9500
C1—C61.403 (4)C17—C181.383 (4)
C2—C31.381 (4)C17—H17A0.9500
C2—H2A0.9500C18—C191.383 (4)
C3—C41.408 (4)C18—H18A0.9500
C3—H3A0.9500C19—H19A0.9500
C4—C51.389 (4)C21—C221.494 (4)
C4—C201.491 (3)C21—H21A0.9900
C5—C61.398 (3)C21—H21B0.9900
C5—H5A0.9500C22—H22A0.9800
C7—C81.479 (3)C22—H22B0.9800
C8—C131.400 (4)C22—H22C0.9800
C8—C91.402 (4)
C20—O1—C21115.6 (2)C12—C13—C8121.0 (2)
C23—O3—C11118.9 (2)C12—C13—H13A119.5
C7—N1—C6105.1 (2)C8—C13—H13A119.5
C1—N2—C7105.7 (2)C15—C14—C19121.2 (2)
C1—N2—C14124.9 (2)C15—C14—N2120.0 (2)
C7—N2—C14129.3 (2)C19—C14—N2118.8 (2)
N2—C1—C2131.5 (2)C16—C15—C14118.8 (3)
N2—C1—C6105.9 (2)C16—C15—H15A120.6
C2—C1—C6122.6 (2)C14—C15—H15A120.6
C3—C2—C1117.1 (2)C17—C16—C15120.4 (3)
C3—C2—H2A121.4C17—C16—H16A119.8
C1—C2—H2A121.4C15—C16—H16A119.8
C2—C3—C4121.0 (2)C18—C17—C16120.2 (3)
C2—C3—H3A119.5C18—C17—H17A119.9
C4—C3—H3A119.5C16—C17—H17A119.9
C5—C4—C3121.8 (2)C19—C18—C17120.2 (3)
C5—C4—C20116.9 (2)C19—C18—H18A119.9
C3—C4—C20121.3 (2)C17—C18—H18A119.9
C4—C5—C6117.5 (2)C18—C19—C14119.1 (3)
C4—C5—H5A121.2C18—C19—H19A120.4
C6—C5—H5A121.2C14—C19—H19A120.4
N1—C6—C5130.0 (2)O2—C20—O1122.9 (2)
N1—C6—C1110.0 (2)O2—C20—C4124.9 (2)
C5—C6—C1120.0 (2)O1—C20—C4112.2 (2)
N1—C7—N2113.3 (2)O1—C21—C22113.5 (2)
N1—C7—C8121.9 (2)O1—C21—H21A108.9
N2—C7—C8124.5 (2)C22—C21—H21A108.9
C13—C8—C9118.2 (2)O1—C21—H21B108.9
C13—C8—C7123.1 (2)C22—C21—H21B108.9
C9—C8—C7118.4 (2)H21A—C21—H21B107.7
C10—C9—C8121.2 (2)C21—C22—H22A109.5
C10—C9—H9A119.4C21—C22—H22B109.5
C8—C9—H9A119.4H22A—C22—H22B109.5
C11—C10—C9118.8 (2)C21—C22—H22C109.5
C11—C10—H10A120.6H22A—C22—H22C109.5
C9—C10—H10A120.6H22B—C22—H22C109.5
C12—C11—C10121.7 (2)F1—C23—O3108.2 (2)
C12—C11—O3123.0 (2)F1—C23—F3108.7 (2)
C10—C11—O3115.2 (2)O3—C23—F3113.3 (2)
C11—C12—C13119.1 (2)F1—C23—F2107.1 (2)
C11—C12—H12A120.4O3—C23—F2113.0 (2)
C13—C12—H12A120.4F3—C23—F2106.4 (2)
C7—N2—C1—C2−178.7 (3)C9—C10—C11—C12−0.1 (4)
C14—N2—C1—C21.3 (4)C9—C10—C11—O3−177.8 (2)
C7—N2—C1—C61.3 (3)C23—O3—C11—C1238.5 (4)
C14—N2—C1—C6−178.7 (2)C23—O3—C11—C10−143.8 (3)
N2—C1—C2—C3178.9 (2)C10—C11—C12—C130.5 (4)
C6—C1—C2—C3−1.1 (4)O3—C11—C12—C13178.1 (2)
C1—C2—C3—C40.3 (4)C11—C12—C13—C8−0.1 (4)
C2—C3—C4—C50.6 (4)C9—C8—C13—C12−0.8 (4)
C2—C3—C4—C20−176.7 (2)C7—C8—C13—C12−174.7 (2)
C3—C4—C5—C6−0.7 (4)C1—N2—C14—C15117.3 (3)
C20—C4—C5—C6176.8 (2)C7—N2—C14—C15−62.7 (4)
C7—N1—C6—C5177.8 (3)C1—N2—C14—C19−64.2 (3)
C7—N1—C6—C10.2 (3)C7—N2—C14—C19115.8 (3)
C4—C5—C6—N1−177.7 (3)C19—C14—C15—C16−2.4 (4)
C4—C5—C6—C1−0.2 (4)N2—C14—C15—C16176.1 (2)
N2—C1—C6—N1−1.0 (3)C14—C15—C16—C171.3 (4)
C2—C1—C6—N1179.1 (2)C15—C16—C17—C180.6 (4)
N2—C1—C6—C5−178.9 (2)C16—C17—C18—C19−1.6 (4)
C2—C1—C6—C51.1 (4)C17—C18—C19—C140.6 (4)
C6—N1—C7—N20.8 (3)C15—C14—C19—C181.4 (4)
C6—N1—C7—C8−173.6 (2)N2—C14—C19—C18−177.1 (2)
C1—N2—C7—N1−1.4 (3)C21—O1—C20—O2−4.3 (4)
C14—N2—C7—N1178.6 (2)C21—O1—C20—C4174.5 (2)
C1—N2—C7—C8172.8 (2)C5—C4—C20—O2−7.8 (4)
C14—N2—C7—C8−7.2 (4)C3—C4—C20—O2169.6 (3)
N1—C7—C8—C13151.2 (3)C5—C4—C20—O1173.4 (2)
N2—C7—C8—C13−22.5 (4)C3—C4—C20—O1−9.2 (3)
N1—C7—C8—C9−22.7 (4)C20—O1—C21—C2279.5 (3)
N2—C7—C8—C9163.6 (2)C11—O3—C23—F1166.4 (2)
C13—C8—C9—C101.3 (4)C11—O3—C23—F345.8 (3)
C7—C8—C9—C10175.5 (2)C11—O3—C23—F2−75.2 (3)
C8—C9—C10—C11−0.9 (4)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg2 are the centroids of the C14–C19 and N1/N2/C1/C6/C7 rings, respectively.

D—H···AD—HH···AD···AD—H···A
C12—H12A···F20.952.372.956 (3)120
C15—H15A···N1i0.952.563.490 (3)167
C18—H18A···O2ii0.952.403.307 (4)160
C19—H19A···O2iii0.952.503.412 (3)160
C13—H13A···Cg10.952.793.592 (3)142
C21—H21A···Cg2iii0.992.953.634 (3)127

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5511).

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