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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o696.
Published online 2008 March 12. doi:  10.1107/S160053680800617X
PMCID: PMC2960893

2,2′-(Decane-1,10-di­yl)dibenz­imid­azo­lium dichloride trihydrate

Abstract

The organic cation in the title compound, C24H32N4 2+·2Cl·3H2O, is situated on an inversion centre. The cations, anions and water mol­ecules are linked via N—H(...)O, N—H(...)Cl, O—H(...)O and O—H(...)Cl hydrogen bonds and C—H(...)π interactions, forming a three-dimensional framework.

Related literature

For general background, see: Day & Arnold (2000 [triangle]); Day et al. (2002 [triangle]); Freeman et al. (1981 [triangle]); Kim et al. (2000 [triangle]); Wang & Joullie (1957 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o696-scheme1.jpg

Experimental

Crystal data

  • C24H32N4 2+·2Cl·3H2O
  • M r = 501.48
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o696-efi1.jpg
  • a = 10.8482 (6) Å
  • b = 11.5089 (6) Å
  • c = 11.9503 (6) Å
  • α = 77.619 (2)°
  • β = 71.501 (2)°
  • γ = 76.030 (2)°
  • V = 1357.58 (13) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 293 (2) K
  • 0.29 × 0.24 × 0.16 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.926, T max = 0.958
  • 13250 measured reflections
  • 4702 independent reflections
  • 3802 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.089
  • S = 1.06
  • 4702 reflections
  • 298 parameters
  • H-atom parameters constrained
  • Δρmax = 0.22 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800617X/rk2079sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800617X/rk2079Isup2.hkl

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

Acknowledgments

We acknowledge the support of the National Natural Science Foundation of China (No. 20662003), the International Collaborative Project of the Ministry of Science and Technology (No. 2007400108) and the Foundation of the Governor of Guizhou Province, China.

supplementary crystallographic information

Comment

We prepared and present a new 'axle' polyaromatic compound (I) containing multiple functional groups that can develop strong intermolecular interactions with cucurbit[n]urils (CB[n]) (Freeman et al., 1981; Day & Arnold, 2000; Day et al., 2002; Kim et al., 2000).

The structure of I, [C24H32N4]2+.2Cl-.3(H2O), contains two independent molecules, which occupy the center of symmetry positions in the middle of C12–C12i and C24–C24ii bonds, respectively (symmetry codes: (i) -x + 2, -y + 3, -z, (ii) -x, -y, -z + 2). The angle between the plane of the phenyl rings and the plane through C10, C11, C12, C12i, C11i, C10i chain is 86.74 (9) Å, and the plane through C22, C23, C24, C24ii, C23ii, C22ii chain is 89.26 (10) Å. The cations, anions and water molecules are linked via N–H···O, N–H···Cl, O–H···O, O–H···Cl hydrogen bonds and C—H···π intreactions forming three–dimensional framework (see table, Cg1, Cg2 are the centroid of the C1/C6–benzene ring and C13/C18–benzene ring, respectively).

Experimental

A solution of o–phenylenedimine (5.40 g, 0.05 mol) and 1,10–decanedicarboxylic acid (5.80 g, 0.025 mol) were reflux for 12 h in 70 ml of 4M HCl, the reaction mixture was cooled for one day and the crystals of I was removed by filtration and dried. The crystals of the title compound suitable for X–ray diffraction were obtained by dissolving in water and standing at room temperature after several days (Wang & Joullie, 1957). Yield: 25%.

Refinement

Water H atoms were located in a difference Fourier synthesis and refined in their as–found positions relative to O atoms with Uiso(H) = 1.2Ueq(O). All other H atoms were placed in calculated positions and refined as riding, with C—H = 0.93–0.97 Å, N—H = 0.86 Å and with Uiso(H) = 1.2Ueq(C, N).

Figures

Fig. 1.
The molecular structure of I with the atom numbering scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius.

Crystal data

C24H32N42+·2Cl·3H2OZ = 2
Mr = 501.48F000 = 536
Triclinic, P1Dx = 1.227 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 10.8482 (6) ÅCell parameters from 13250 reflections
b = 11.5089 (6) Åθ = 1.8–25.0º
c = 11.9503 (6) ŵ = 0.27 mm1
α = 77.619 (2)ºT = 293 (2) K
β = 71.501 (2)ºPrism, colourless
γ = 76.030 (2)º0.29 × 0.24 × 0.16 mm
V = 1357.58 (13) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer4702 independent reflections
Radiation source: Fine–focus sealed tube3802 reflections with I > 2σ(I)
Monochromator: GraphiteRint = 0.024
T = 293(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −12→12
Tmin = 0.926, Tmax = 0.958k = −12→13
13250 measured reflectionsl = −11→14

Refinement

Refinement on F2Secondary atom site location: Difmap
Least-squares matrix: FullHydrogen site location: Geom
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.089  w = 1/[σ2(Fo2) + (0.0377P)2 + 0.299P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
4702 reflectionsΔρmax = 0.22 e Å3
298 parametersΔρmin = −0.18 e Å3
Primary atom site location: DirectExtinction correction: none

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 RR–factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
C10.64008 (18)0.65504 (16)0.11143 (15)0.0407 (4)
C20.6254 (2)0.78026 (18)0.09401 (19)0.0572 (5)
H20.54470.83080.09230.069*
C30.7371 (2)0.8257 (2)0.07942 (19)0.0624 (6)
H30.73170.90910.06680.075*
C40.8579 (2)0.7500 (2)0.08310 (17)0.0570 (6)
H40.93070.78450.07290.068*
C50.87257 (19)0.62624 (19)0.10132 (16)0.0487 (5)
H50.95300.57590.10430.058*
C60.76037 (17)0.58019 (16)0.11513 (15)0.0387 (4)
C70.61491 (17)0.46486 (15)0.13702 (15)0.0364 (4)
C80.55400 (18)0.35944 (16)0.14626 (17)0.0418 (4)
H8A0.58510.33150.06930.050*
H8B0.45890.38640.16340.050*
C90.58230 (18)0.25312 (15)0.24031 (15)0.0392 (4)
H9A0.54730.27830.31860.047*
H9B0.67720.22600.22550.047*
C100.51925 (18)0.14950 (16)0.23773 (16)0.0409 (4)
H10A0.42430.17710.25480.049*
H10B0.55140.12810.15790.049*
C110.54728 (18)0.03713 (16)0.32589 (16)0.0415 (4)
H11A0.64220.00920.30850.050*
H11B0.5093−0.02630.31480.050*
C120.49251 (16)0.05731 (15)0.45552 (15)0.0384 (4)
H12A0.53740.11440.46860.046*
H12B0.39940.09350.47050.046*
C130.16012 (15)−0.00823 (15)0.50147 (15)0.0340 (4)
C140.19499 (17)−0.13242 (16)0.50035 (18)0.0430 (4)
H140.1875−0.18770.57030.052*
C150.24119 (18)−0.16880 (18)0.38967 (19)0.0484 (5)
H150.2662−0.25110.38480.058*
C160.25169 (17)−0.08601 (18)0.28440 (18)0.0463 (5)
H160.2826−0.11480.21160.056*
C170.21752 (16)0.03697 (17)0.28543 (16)0.0405 (4)
H170.22460.09210.21530.049*
C180.17194 (15)0.07423 (15)0.39687 (15)0.0329 (4)
C190.09620 (15)0.17706 (16)0.55014 (15)0.0353 (4)
C200.04445 (17)0.27781 (17)0.62225 (17)0.0454 (5)
H20A0.05250.24690.70230.055*
H20B−0.04890.30560.62830.055*
C210.11453 (17)0.38577 (16)0.57205 (17)0.0436 (4)
H21A0.10860.41540.49120.052*
H21B0.06850.45020.61940.052*
C220.25918 (16)0.35777 (15)0.57035 (17)0.0398 (4)
H22A0.26590.32660.65070.048*
H22B0.30640.29520.52100.048*
C230.32401 (18)0.46815 (16)0.52292 (18)0.0463 (5)
H23A0.27250.53240.56880.056*
H23B0.32200.49590.44080.056*
C240.46640 (18)0.44573 (17)0.52768 (17)0.0453 (5)
H24A0.46780.42350.61030.054*
H24B0.51670.37780.48640.054*
Cl10.18425 (5)0.85742 (4)0.02569 (4)0.04826 (14)
Cl20.16011 (5)0.39667 (4)0.21933 (4)0.05033 (15)
N10.55187 (14)0.57926 (12)0.12641 (13)0.0397 (4)
H10.46980.60270.12850.048*
N20.73979 (14)0.46237 (13)0.13165 (13)0.0400 (4)
H2A0.79860.39790.13750.048*
N30.11251 (13)0.06012 (13)0.59441 (12)0.0362 (3)
H3A0.09620.03110.66910.043*
N40.13153 (13)0.18871 (12)0.43127 (12)0.0355 (3)
H4A0.12960.25620.38350.043*
O1W0.95820 (12)0.03649 (11)0.16974 (10)0.0452 (3)
H1WA1.0290−0.00600.12850.054*
H1WB0.90390.06430.12350.054*
O3W0.28364 (12)0.62540 (11)0.18261 (12)0.0529 (4)
H3WA0.23950.56270.19630.063*
H3WB0.24430.68400.13150.063*
O2W0.92820 (12)0.28229 (11)0.20533 (12)0.0494 (3)
H2WA0.96160.20210.18290.059*
H2WB0.99700.31570.19960.059*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0453 (10)0.0372 (10)0.0372 (10)−0.0113 (8)−0.0083 (8)−0.0014 (8)
C20.0637 (13)0.0390 (12)0.0617 (14)−0.0091 (10)−0.0123 (11)−0.0012 (10)
C30.0850 (17)0.0438 (12)0.0578 (14)−0.0296 (12)−0.0094 (12)−0.0023 (10)
C40.0653 (14)0.0640 (14)0.0463 (12)−0.0362 (12)−0.0062 (10)−0.0053 (10)
C50.0473 (11)0.0588 (13)0.0423 (11)−0.0208 (10)−0.0090 (9)−0.0059 (9)
C60.0433 (10)0.0390 (10)0.0324 (10)−0.0116 (8)−0.0085 (8)−0.0016 (8)
C70.0371 (9)0.0377 (10)0.0343 (10)−0.0082 (8)−0.0114 (8)−0.0013 (7)
C80.0403 (10)0.0391 (10)0.0481 (11)−0.0069 (8)−0.0169 (8)−0.0044 (8)
C90.0433 (10)0.0389 (10)0.0368 (10)−0.0119 (8)−0.0108 (8)−0.0044 (8)
C100.0404 (10)0.0415 (10)0.0437 (11)−0.0131 (8)−0.0119 (8)−0.0062 (8)
C110.0398 (10)0.0373 (10)0.0492 (11)−0.0105 (8)−0.0119 (8)−0.0079 (8)
C120.0334 (9)0.0320 (9)0.0507 (11)−0.0080 (8)−0.0123 (8)−0.0050 (8)
C130.0280 (8)0.0401 (10)0.0370 (10)−0.0090 (7)−0.0113 (7)−0.0061 (8)
C140.0382 (10)0.0393 (11)0.0549 (12)−0.0098 (8)−0.0197 (9)−0.0012 (9)
C150.0408 (10)0.0416 (11)0.0704 (14)−0.0061 (9)−0.0215 (10)−0.0174 (10)
C160.0375 (10)0.0571 (13)0.0533 (12)−0.0097 (9)−0.0144 (9)−0.0235 (10)
C170.0351 (9)0.0524 (12)0.0382 (10)−0.0133 (8)−0.0123 (8)−0.0068 (8)
C180.0266 (8)0.0361 (10)0.0392 (10)−0.0091 (7)−0.0113 (7)−0.0058 (8)
C190.0247 (8)0.0436 (11)0.0397 (10)−0.0099 (7)−0.0085 (7)−0.0080 (8)
C200.0326 (9)0.0541 (12)0.0511 (12)−0.0083 (8)−0.0063 (8)−0.0192 (9)
C210.0388 (10)0.0386 (10)0.0543 (12)−0.0002 (8)−0.0137 (9)−0.0163 (9)
C220.0382 (10)0.0346 (10)0.0471 (11)−0.0055 (8)−0.0121 (8)−0.0087 (8)
C230.0490 (11)0.0386 (11)0.0537 (12)−0.0111 (9)−0.0149 (9)−0.0084 (9)
C240.0477 (11)0.0462 (11)0.0463 (11)−0.0153 (9)−0.0126 (9)−0.0093 (9)
Cl10.0498 (3)0.0453 (3)0.0464 (3)0.0017 (2)−0.0178 (2)−0.0055 (2)
Cl20.0542 (3)0.0429 (3)0.0557 (3)−0.0152 (2)−0.0192 (2)0.0017 (2)
N10.0358 (8)0.0348 (9)0.0464 (9)−0.0034 (7)−0.0143 (7)−0.0009 (7)
N20.0367 (8)0.0351 (8)0.0469 (9)−0.0047 (6)−0.0129 (7)−0.0037 (7)
N30.0331 (8)0.0430 (9)0.0337 (8)−0.0114 (6)−0.0105 (6)−0.0015 (7)
N40.0336 (7)0.0336 (8)0.0386 (9)−0.0086 (6)−0.0103 (6)−0.0012 (6)
O1W0.0441 (7)0.0501 (8)0.0374 (7)0.0007 (6)−0.0125 (6)−0.0075 (6)
O3W0.0435 (7)0.0373 (7)0.0740 (10)−0.0072 (6)−0.0192 (7)0.0034 (6)
O2W0.0416 (7)0.0412 (7)0.0683 (9)−0.0058 (6)−0.0202 (6)−0.0092 (6)

Geometric parameters (Å, °)

C1—C61.387 (3)C15—C161.397 (3)
C1—C21.388 (3)C15—H150.9300
C1—N11.391 (2)C16—C171.376 (3)
C2—C31.380 (3)C16—H160.9300
C2—H20.9300C17—C181.388 (2)
C3—C41.396 (3)C17—H170.9300
C3—H30.9300C18—N41.391 (2)
C4—C51.372 (3)C19—N31.327 (2)
C4—H40.9300C19—N41.334 (2)
C5—C61.392 (2)C19—C201.486 (2)
C5—H50.9300C20—C211.526 (2)
C6—N21.390 (2)C20—H20A0.9700
C7—N11.329 (2)C20—H20B0.9700
C7—N21.329 (2)C21—C221.518 (2)
C7—C81.485 (2)C21—H21A0.9700
C8—C91.517 (2)C21—H21B0.9700
C8—H8A0.9700C22—C231.516 (2)
C8—H8B0.9700C22—H22A0.9700
C9—C101.521 (2)C22—H22B0.9700
C9—H9A0.9700C23—C241.521 (3)
C9—H9B0.9700C23—H23A0.9700
C10—C111.518 (2)C23—H23B0.9700
C10—H10A0.9700C24—C24ii1.520 (3)
C10—H10B0.9700C24—H24A0.9700
C11—C121.520 (2)C24—H24B0.9700
C11—H11A0.9700N1—H10.8600
C11—H11B0.9700N2—H2A0.8600
C12—C12i1.517 (3)N3—H3A0.8600
C12—H12A0.9700N4—H4A0.8600
C12—H12B0.9700O1W—H1WA0.8680
C13—C181.388 (2)O1W—H1WB0.8916
C13—C141.389 (2)O3W—H3WA0.9188
C13—N31.390 (2)O3W—H3WB0.9275
C14—C151.375 (3)O2W—H2WA0.9681
C14—H140.9300O2W—H2WB0.8971
C6—C1—C2121.54 (18)C16—C15—H15119.0
C6—C1—N1106.43 (15)C17—C16—C15121.84 (18)
C2—C1—N1132.02 (18)C17—C16—H16119.1
C3—C2—C1116.3 (2)C15—C16—H16119.1
C3—C2—H2121.8C16—C17—C18116.30 (17)
C1—C2—H2121.8C16—C17—H17121.8
C2—C3—C4121.9 (2)C18—C17—H17121.8
C2—C3—H3119.0C17—C18—C13121.77 (16)
C4—C3—H3119.0C17—C18—N4131.94 (16)
C5—C4—C3121.93 (19)C13—C18—N4106.29 (14)
C5—C4—H4119.0N3—C19—N4108.88 (15)
C3—C4—H4119.0N3—C19—C20125.13 (16)
C4—C5—C6116.28 (19)N4—C19—C20125.99 (16)
C4—C5—H5121.9C19—C20—C21114.39 (15)
C6—C5—H5121.9C19—C20—H20A108.7
C1—C6—N2106.09 (15)C21—C20—H20A108.7
C1—C6—C5121.99 (17)C19—C20—H20B108.7
N2—C6—C5131.91 (17)C21—C20—H20B108.7
N1—C7—N2109.12 (15)H20A—C20—H20B107.6
N1—C7—C8123.98 (15)C22—C21—C20114.17 (15)
N2—C7—C8126.82 (16)C22—C21—H21A108.7
C7—C8—C9115.36 (15)C20—C21—H21A108.7
C7—C8—H8A108.4C22—C21—H21B108.7
C9—C8—H8A108.4C20—C21—H21B108.7
C7—C8—H8B108.4H21A—C21—H21B107.6
C9—C8—H8B108.4C23—C22—C21112.45 (15)
H8A—C8—H8B107.5C23—C22—H22A109.1
C8—C9—C10110.33 (14)C21—C22—H22A109.1
C8—C9—H9A109.6C23—C22—H22B109.1
C10—C9—H9A109.6C21—C22—H22B109.1
C8—C9—H9B109.6H22A—C22—H22B107.8
C10—C9—H9B109.6C22—C23—C24114.00 (16)
H9A—C9—H9B108.1C22—C23—H23A108.8
C11—C10—C9113.90 (14)C24—C23—H23A108.8
C11—C10—H10A108.8C22—C23—H23B108.8
C9—C10—H10A108.8C24—C23—H23B108.8
C11—C10—H10B108.8H23A—C23—H23B107.6
C9—C10—H10B108.8C24ii—C24—C23113.7 (2)
H10A—C10—H10B107.7C24ii—C24—H24A108.8
C10—C11—C12113.70 (15)C23—C24—H24A108.8
C10—C11—H11A108.8C24ii—C24—H24B108.8
C12—C11—H11A108.8C23—C24—H24B108.8
C10—C11—H11B108.8H24A—C24—H24B107.7
C12—C11—H11B108.8C7—N1—C1109.03 (14)
H11A—C11—H11B107.7C7—N1—H1125.5
C12i—C12—C11113.96 (18)C1—N1—H1125.5
C12i—C12—H12A108.8C7—N2—C6109.33 (15)
C11—C12—H12A108.8C7—N2—H2A125.3
C12i—C12—H12B108.8C6—N2—H2A125.3
C11—C12—H12B108.8C19—N3—C13109.52 (14)
H12A—C12—H12B107.7C19—N3—H3A125.2
C18—C13—C14121.89 (16)C13—N3—H3A125.2
C18—C13—N3106.14 (14)C19—N4—C18109.17 (14)
C14—C13—N3131.96 (16)C19—N4—H4A125.4
C15—C14—C13116.09 (17)C18—N4—H4A125.4
C15—C14—H14122.0H1WA—O1W—H1WB107.0
C13—C14—H14122.0H3WA—O3W—H3WB103.3
C14—C15—C16122.10 (18)H2WA—O2W—H2WB108.7
C14—C15—H15119.0
C6—C1—C2—C30.7 (3)N3—C13—C18—C17179.89 (14)
N1—C1—C2—C3−178.45 (19)C14—C13—C18—N4−178.69 (14)
C1—C2—C3—C4−0.6 (3)N3—C13—C18—N40.28 (16)
C2—C3—C4—C50.1 (3)N3—C19—C20—C21140.24 (17)
C3—C4—C5—C60.4 (3)N4—C19—C20—C21−41.0 (2)
C2—C1—C6—N2−179.04 (17)C19—C20—C21—C22−64.7 (2)
N1—C1—C6—N20.27 (19)C20—C21—C22—C23−178.49 (16)
C2—C1—C6—C5−0.2 (3)C21—C22—C23—C24176.07 (16)
N1—C1—C6—C5179.12 (16)C22—C23—C24—C24ii176.07 (19)
C4—C5—C6—C1−0.4 (3)N2—C7—N1—C11.0 (2)
C4—C5—C6—N2178.15 (18)C8—C7—N1—C1−175.79 (16)
N1—C7—C8—C9−136.00 (18)C6—C1—N1—C7−0.79 (19)
N2—C7—C8—C947.8 (2)C2—C1—N1—C7178.4 (2)
C7—C8—C9—C10−177.80 (16)N1—C7—N2—C6−0.9 (2)
C8—C9—C10—C11177.68 (15)C8—C7—N2—C6175.85 (16)
C9—C10—C11—C1262.6 (2)C1—C6—N2—C70.35 (19)
C10—C11—C12—C12i173.94 (17)C5—C6—N2—C7−178.35 (19)
C18—C13—C14—C15−0.3 (2)N4—C19—N3—C13−0.13 (17)
N3—C13—C14—C15−178.99 (16)C20—C19—N3—C13178.79 (15)
C13—C14—C15—C16−0.4 (3)C18—C13—N3—C19−0.10 (17)
C14—C15—C16—C170.6 (3)C14—C13—N3—C19178.73 (17)
C15—C16—C17—C18−0.1 (2)N3—C19—N4—C180.31 (17)
C16—C17—C18—C13−0.7 (2)C20—C19—N4—C18−178.60 (15)
C16—C17—C18—N4178.80 (16)C17—C18—N4—C19−179.93 (17)
C14—C13—C18—C170.9 (2)C13—C18—N4—C19−0.37 (17)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O3W0.861.882.7142 (19)162
N2—H2A···O2W0.861.942.7500 (19)157
N3—H3A···O1Wi0.861.882.7322 (18)173
N4—H4A···Cl20.862.253.0823 (15)163
O1W—H1WA···Cl1iii0.872.253.1027 (13)168
O1W—H1WB···Cl1iv0.892.213.0804 (13)166
O2W—H2WA···O1W0.971.962.8763 (18)158
O2W—H2WB···Cl2v0.902.283.1703 (13)170
O3W—H3WB···Cl10.932.203.0912 (13)162
O3W—H3WA···Cl20.922.213.1229 (13)172
C11—H11B···Cg20.973.173.847 (3)128
C22—H22A···Cg1ii0.972.923.863 (3)165

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2079).

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