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In the crystal structure of the title 1:2 salt, C10H22N22+·2C6HCl2O4, the 4,4′-bipiperidinium dication and the two hydrogen chloranilate anions are held together by N—H...O and C—H...O hydrogen bonds. Two 1:2 units are connected by O—H...O hydrogen bonds, forming a centrosymmetric mol­ecular ring. The rings are further linked by O—H...O, N—H...O and C—H...O hydrogen bonds, leading to a three-dimensional hydrogen-bonding network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705386X/hg2333sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680705386X/hg2333Isup2.hkl
Contains datablock I

CCDC reference: 672796

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.088
  • Data-to-parameter ratio = 20.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT335_ALERT_2_C Large Benzene C-C Range ....... C1 -C6 0.20 Ang. PLAT335_ALERT_2_C Large Benzene C-C Range ....... C7 -C12 0.20 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C6 ... 1.54 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C7 - C12 ... 1.55 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C3 .. 2.93 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact C9 .. C11 .. 3.13 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The title compound, (I), was prepared in order to extend our study on D—H···A hydrogen bonding (D = N, O, or C; A = N, O or Cl) in amine – chloranilic acid (1/1) and (2/1) systems (Ishida, 2004; Refat et al., 2006). To our knowledge, this is the first crystallographic report of the amine – chloranilic acid (1/2) system; no structural data of compounds of the (1/2) system are recorded in the Cambridge Structural Database, version 5.28 (2007 Release; Allen, 2002).

The asymmetric unit in the title compound contains one 4,4'-bipiperidinium dication and two hydrogen chloranilate anions, which are connected by N—H···O, bifurcated N—H···O and C—H···O hydrogen bonds (Table 1) to form a 1:2 unit (Fig. 1). The two units related by an inversion center are held together through O—H···O hydrogen bonds, forming a macro molecular ring (Fig. 2). The rings are further connected by O—H···O, N—H···O and C—H···O hydrogen bonds, leading to a three-dimensional hydrogen-bonding network.

Related literature top

For related literature, see: Allen (2002); Ishida (2004); Refat et al. (2006).

Experimental top

Single crystals were obtained by slow evaporation from a methanol solution of chloranilic acid (63 mg) with 4,4'-bipiperidyl dihydrochloride (36 mg).

Refinement top

N– and O-bound H atoms were located in a difference Fourier map and refined isotropically (refined distances are given in Table 1). Other H atoms were positioned geometrically (C—H = 0.98 or 0.99 Å) and refined as riding, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: PROCESS-AUTO (Rigaku/MSC, 2004); cell refinement: PROCESS-AUTO (Rigaku/MSC, 2004); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with the atom numbering. Displacement ellipsoids of non-H atoms are drawn at the 50% probability level. N—H···O and C—H···O hydrogen bonds are indicated by dashed lines.
[Figure 2] Fig. 2. A partial packing diagram, viewed approximately along the b axis, showing the centrosymmetric molecular ring formed by O—H···O, N—H···O and C—H···O hydrogen bonds (dashed lines) [symmetry code (i) is as given in Table 1].
4,4'-Bipiperidinium bis(hydrogen chloranilate) top
Crystal data top
C10H22N22+·2C6HCl2O4F(000) = 1208.00
Mr = 586.25Dx = 1.624 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2ynCell parameters from 27745 reflections
a = 17.4716 (10) Åθ = 3.2–30.1°
b = 7.7132 (4) ŵ = 0.55 mm1
c = 19.1252 (11) ÅT = 100 K
β = 111.5434 (19)°Needle, purple
V = 2397.3 (2) Å30.25 × 0.17 × 0.12 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
5848 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm-1Rint = 0.035
ω scansθmax = 30.0°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 2423
Tmin = 0.850, Tmax = 0.937k = 1010
26002 measured reflectionsl = 2626
6982 independent reflections
Refinement top
Refinement on F20 restraints
R[F2 > 2σ(F2)] = 0.040H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.0399P)2 + 1.34P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
6982 reflectionsΔρmax = 0.43 e Å3
349 parametersΔρmin = 0.29 e Å3
Crystal data top
C10H22N22+·2C6HCl2O4V = 2397.3 (2) Å3
Mr = 586.25Z = 4
Monoclinic, P21/nMo Kα radiation
a = 17.4716 (10) ŵ = 0.55 mm1
b = 7.7132 (4) ÅT = 100 K
c = 19.1252 (11) Å0.25 × 0.17 × 0.12 mm
β = 111.5434 (19)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
6982 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
5848 reflections with I > 2σ(I)
Tmin = 0.850, Tmax = 0.937Rint = 0.035
26002 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.43 e Å3
6982 reflectionsΔρmin = 0.29 e Å3
349 parameters
Special details top

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) top
xyzUiso*/Ueq
Cl10.40240 (2)0.05182 (5)0.45568 (2)0.01654 (8)
Cl20.10315 (2)0.00510 (6)0.14248 (2)0.01867 (9)
Cl30.79278 (2)0.95757 (6)0.30125 (2)0.02012 (9)
Cl41.08946 (2)0.66212 (5)0.58222 (2)0.01466 (8)
O10.40238 (7)0.07957 (16)0.31131 (7)0.0174 (2)
O20.22655 (7)0.13356 (15)0.42519 (6)0.0139 (2)
O30.10072 (7)0.08933 (15)0.29685 (6)0.0143 (2)
O40.28393 (7)0.05474 (16)0.17399 (6)0.0165 (2)
O50.78585 (7)0.73421 (16)0.42744 (6)0.0163 (2)
O60.97184 (7)1.01381 (15)0.33987 (6)0.0141 (2)
O71.09316 (7)0.88325 (15)0.45278 (6)0.0151 (2)
O80.90753 (7)0.66571 (16)0.55947 (6)0.0163 (2)
N10.48752 (8)0.08134 (18)0.21307 (7)0.0127 (2)
N20.72848 (8)0.49927 (18)0.51771 (8)0.0137 (3)
C10.33488 (9)0.0260 (2)0.30686 (8)0.0120 (3)
C20.31958 (9)0.0360 (2)0.37204 (8)0.0120 (3)
C30.24259 (9)0.07760 (19)0.36626 (8)0.0109 (3)
C40.16933 (9)0.05946 (19)0.29323 (8)0.0112 (3)
C50.18512 (9)0.0135 (2)0.22824 (8)0.0132 (3)
C60.26422 (9)0.0220 (2)0.22931 (8)0.0119 (3)
C70.85514 (9)0.7831 (2)0.43545 (8)0.0119 (3)
C80.87308 (9)0.8865 (2)0.37990 (8)0.0127 (3)
C90.95195 (9)0.9208 (2)0.38904 (8)0.0115 (3)
C101.02423 (9)0.84710 (19)0.45370 (8)0.0111 (3)
C111.00710 (9)0.7486 (2)0.50857 (8)0.0115 (3)
C120.92737 (9)0.72772 (19)0.50780 (8)0.0116 (3)
C130.48474 (10)0.1099 (2)0.19929 (9)0.0160 (3)
H50.42850.14390.16820.019*
H60.52050.13860.17170.019*
C140.51248 (10)0.2110 (2)0.27274 (8)0.0138 (3)
H70.47360.19060.29800.017*
H80.51190.33530.26180.017*
C150.59924 (9)0.1584 (2)0.32548 (8)0.0113 (3)
H90.63840.18550.30050.014*
C160.59974 (9)0.0392 (2)0.33798 (8)0.0123 (3)
H100.65570.07600.36890.015*
H110.56380.06650.36560.015*
C170.57093 (10)0.1400 (2)0.26450 (9)0.0146 (3)
H120.61040.12390.23960.018*
H130.56900.26390.27510.018*
C180.73772 (10)0.3062 (2)0.52769 (9)0.0148 (3)
H160.70310.26510.55470.018*
H170.79500.27870.55830.018*
C190.71351 (9)0.2121 (2)0.45278 (9)0.0140 (3)
H180.71720.08670.46160.017*
H190.75220.24290.42840.017*
C200.62581 (9)0.25870 (19)0.40037 (8)0.0107 (3)
H200.58790.22680.42600.013*
C210.62210 (9)0.4567 (2)0.38979 (8)0.0129 (3)
H210.66000.49140.36520.015*
H220.56640.49040.35710.015*
C220.64503 (10)0.5509 (2)0.46465 (9)0.0147 (3)
H230.64400.67630.45610.018*
H240.60430.52430.48720.018*
H10.1747 (15)0.161 (3)0.4119 (13)0.032 (6)*
H21.0218 (16)1.013 (3)0.3529 (14)0.034 (7)*
H30.4514 (13)0.111 (3)0.2344 (12)0.018 (5)*
H40.4730 (13)0.133 (3)0.1706 (12)0.016 (5)*
H140.7663 (13)0.542 (3)0.5008 (12)0.019 (5)*
H150.7399 (13)0.543 (3)0.5629 (12)0.016 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01155 (15)0.02349 (19)0.01206 (16)0.00183 (14)0.00137 (13)0.00107 (14)
Cl20.01405 (16)0.0287 (2)0.01102 (16)0.00135 (15)0.00191 (13)0.00284 (14)
Cl30.01221 (16)0.0314 (2)0.01461 (17)0.00159 (15)0.00244 (13)0.00730 (15)
Cl40.01224 (15)0.01595 (17)0.01420 (16)0.00208 (13)0.00299 (13)0.00227 (13)
O10.0131 (5)0.0216 (6)0.0191 (6)0.0026 (5)0.0079 (4)0.0011 (5)
O20.0126 (5)0.0195 (6)0.0107 (5)0.0015 (4)0.0055 (4)0.0016 (4)
O30.0116 (5)0.0166 (5)0.0158 (5)0.0000 (4)0.0065 (4)0.0001 (4)
O40.0188 (5)0.0202 (6)0.0128 (5)0.0025 (5)0.0086 (4)0.0007 (4)
O50.0109 (5)0.0209 (6)0.0173 (5)0.0021 (4)0.0055 (4)0.0020 (5)
O60.0130 (5)0.0166 (5)0.0148 (5)0.0004 (4)0.0075 (4)0.0030 (4)
O70.0112 (5)0.0180 (6)0.0176 (5)0.0010 (4)0.0069 (4)0.0003 (4)
O80.0148 (5)0.0212 (6)0.0145 (5)0.0008 (5)0.0074 (4)0.0045 (4)
N10.0135 (6)0.0140 (6)0.0102 (6)0.0026 (5)0.0038 (5)0.0022 (5)
N20.0137 (6)0.0147 (6)0.0124 (6)0.0038 (5)0.0043 (5)0.0030 (5)
C10.0129 (6)0.0113 (7)0.0128 (7)0.0007 (5)0.0058 (5)0.0006 (5)
C20.0109 (6)0.0147 (7)0.0094 (6)0.0002 (5)0.0025 (5)0.0002 (5)
C30.0130 (6)0.0100 (6)0.0109 (6)0.0001 (5)0.0057 (5)0.0008 (5)
C40.0112 (6)0.0105 (6)0.0123 (6)0.0012 (5)0.0048 (5)0.0005 (5)
C50.0116 (6)0.0172 (7)0.0096 (6)0.0007 (6)0.0024 (5)0.0013 (5)
C60.0133 (6)0.0111 (6)0.0120 (6)0.0005 (5)0.0054 (5)0.0008 (5)
C70.0126 (6)0.0129 (7)0.0113 (6)0.0008 (5)0.0057 (5)0.0003 (5)
C80.0114 (6)0.0161 (7)0.0095 (6)0.0009 (6)0.0027 (5)0.0011 (5)
C90.0141 (6)0.0109 (6)0.0113 (6)0.0000 (5)0.0069 (5)0.0001 (5)
C100.0122 (6)0.0105 (6)0.0111 (6)0.0001 (5)0.0047 (5)0.0024 (5)
C110.0107 (6)0.0119 (7)0.0106 (6)0.0012 (5)0.0023 (5)0.0001 (5)
C120.0125 (6)0.0101 (6)0.0124 (6)0.0006 (5)0.0049 (5)0.0010 (5)
C130.0194 (7)0.0137 (7)0.0109 (7)0.0008 (6)0.0007 (6)0.0017 (6)
C140.0160 (7)0.0107 (6)0.0109 (6)0.0008 (6)0.0004 (5)0.0000 (5)
C150.0118 (6)0.0110 (6)0.0105 (6)0.0003 (5)0.0035 (5)0.0003 (5)
C160.0129 (6)0.0108 (7)0.0115 (6)0.0009 (5)0.0023 (5)0.0007 (5)
C170.0158 (7)0.0133 (7)0.0130 (7)0.0020 (6)0.0033 (6)0.0008 (5)
C180.0141 (7)0.0129 (7)0.0138 (7)0.0003 (6)0.0011 (6)0.0001 (6)
C190.0121 (6)0.0143 (7)0.0126 (7)0.0015 (6)0.0011 (5)0.0028 (6)
C200.0109 (6)0.0107 (6)0.0097 (6)0.0004 (5)0.0030 (5)0.0003 (5)
C210.0141 (7)0.0110 (6)0.0121 (7)0.0007 (5)0.0031 (5)0.0001 (5)
C220.0153 (7)0.0133 (7)0.0144 (7)0.0010 (6)0.0039 (6)0.0007 (6)
Geometric parameters (Å, º) top
Cl1—C21.7227 (15)C9—C101.517 (2)
Cl2—C51.7379 (15)C10—C111.414 (2)
Cl3—C81.7267 (15)C11—C121.397 (2)
Cl4—C111.7350 (15)C13—C141.522 (2)
O1—C11.2226 (18)C13—H50.9800
O2—C31.3293 (18)C13—H60.9800
O2—H10.87 (2)C14—C151.535 (2)
O3—C41.2474 (18)C14—H70.9800
O4—C61.2527 (18)C14—H80.9800
O5—C71.2228 (18)C15—C201.542 (2)
O6—C91.3264 (18)C15—C161.543 (2)
O6—H20.82 (3)C15—H90.9900
O7—C101.2425 (18)C16—C171.521 (2)
O8—C121.2557 (18)C16—H100.9800
N1—C131.496 (2)C16—H110.9800
N1—C171.498 (2)C17—H120.9800
N1—H30.90 (2)C17—H130.9800
N1—H40.86 (2)C18—C191.521 (2)
N2—C221.493 (2)C18—H160.9800
N2—C181.502 (2)C18—H170.9800
N2—H140.90 (2)C19—C201.534 (2)
N2—H150.88 (2)C19—H180.9800
C1—C21.449 (2)C19—H190.9800
C1—C61.543 (2)C20—C211.539 (2)
C2—C31.347 (2)C20—H200.9900
C3—C41.515 (2)C21—C221.522 (2)
C4—C51.414 (2)C21—H210.9800
C5—C61.402 (2)C21—H220.9800
C7—C81.452 (2)C22—H230.9800
C7—C121.551 (2)C22—H240.9800
C8—C91.350 (2)
C3—O2—H1110.6 (16)H5—C13—H6108.0
C9—O6—H2107.9 (18)C13—C14—C15111.96 (13)
C13—N1—C17111.98 (12)C13—C14—H7109.2
C13—N1—H3110.4 (14)C15—C14—H7109.2
C17—N1—H3107.6 (14)C13—C14—H8109.2
C13—N1—H4108.4 (14)C15—C14—H8109.2
C17—N1—H4111.0 (14)H7—C14—H8107.9
H3—N1—H4107.4 (19)C14—C15—C20111.45 (12)
C22—N2—C18112.55 (12)C14—C15—C16108.11 (12)
C22—N2—H14108.7 (14)C20—C15—C16111.67 (12)
C18—N2—H14110.6 (14)C14—C15—H9108.5
C22—N2—H15112.2 (14)C20—C15—H9108.5
C18—N2—H15106.2 (14)C16—C15—H9108.5
H14—N2—H15106.3 (19)C17—C16—C15112.39 (12)
O1—C1—C2121.98 (14)C17—C16—H10109.1
O1—C1—C6118.99 (13)C15—C16—H10109.1
C2—C1—C6119.02 (13)C17—C16—H11109.1
C3—C2—C1120.14 (14)C15—C16—H11109.1
C3—C2—Cl1122.14 (12)H10—C16—H11107.9
C1—C2—Cl1117.71 (11)N1—C17—C16111.37 (13)
O2—C3—C2121.52 (14)N1—C17—H12109.4
O2—C3—C4116.22 (13)C16—C17—H12109.4
C2—C3—C4122.25 (13)N1—C17—H13109.4
O3—C4—C5126.65 (14)C16—C17—H13109.4
O3—C4—C3115.82 (13)H12—C17—H13108.0
C5—C4—C3117.52 (13)N2—C18—C19111.94 (13)
C6—C5—C4123.08 (14)N2—C18—H16109.2
C6—C5—Cl2118.23 (11)C19—C18—H16109.2
C4—C5—Cl2118.68 (11)N2—C18—H17109.2
O4—C6—C5127.04 (14)C19—C18—H17109.2
O4—C6—C1115.89 (13)H16—C18—H17107.9
C5—C6—C1117.05 (13)C18—C19—C20111.67 (13)
O5—C7—C8123.20 (14)C18—C19—H18109.3
O5—C7—C12118.06 (13)C20—C19—H18109.3
C8—C7—C12118.72 (13)C18—C19—H19109.3
C9—C8—C7119.82 (14)C20—C19—H19109.3
C9—C8—Cl3120.98 (12)H18—C19—H19107.9
C7—C8—Cl3119.16 (11)C19—C20—C21107.58 (12)
O6—C9—C8122.33 (14)C19—C20—C15112.17 (12)
O6—C9—C10115.10 (13)C21—C20—C15113.08 (12)
C8—C9—C10122.47 (13)C19—C20—H20107.9
O7—C10—C11126.98 (14)C21—C20—H20107.9
O7—C10—C9115.18 (13)C15—C20—H20107.9
C11—C10—C9117.83 (13)C22—C21—C20111.48 (12)
C12—C11—C10122.41 (13)C22—C21—H21109.3
C12—C11—Cl4119.40 (12)C20—C21—H21109.3
C10—C11—Cl4118.08 (11)C22—C21—H22109.3
O8—C12—C11126.71 (14)C20—C21—H22109.3
O8—C12—C7115.95 (13)H21—C21—H22108.0
C11—C12—C7117.33 (13)N2—C22—C21111.48 (13)
N1—C13—C14111.34 (12)N2—C22—H23109.3
N1—C13—H5109.4C21—C22—H23109.3
C14—C13—H5109.4N2—C22—H24109.3
N1—C13—H6109.4C21—C22—H24109.3
C14—C13—H6109.4H23—C22—H24108.0
O1—C1—C2—C3173.35 (15)O6—C9—C10—C11179.20 (13)
C6—C1—C2—C37.5 (2)C8—C9—C10—C114.3 (2)
O1—C1—C2—Cl16.1 (2)O7—C10—C11—C12174.38 (15)
C6—C1—C2—Cl1173.04 (11)C9—C10—C11—C124.5 (2)
C1—C2—C3—O2179.49 (14)O7—C10—C11—Cl41.7 (2)
Cl1—C2—C3—O20.1 (2)C9—C10—C11—Cl4179.40 (11)
C1—C2—C3—C41.0 (2)C10—C11—C12—O8168.50 (15)
Cl1—C2—C3—C4178.42 (11)Cl4—C11—C12—O87.5 (2)
O2—C3—C4—O34.0 (2)C10—C11—C12—C712.7 (2)
C2—C3—C4—O3174.57 (15)Cl4—C11—C12—C7171.22 (11)
O2—C3—C4—C5175.08 (14)O5—C7—C12—O813.5 (2)
C2—C3—C4—C56.3 (2)C8—C7—C12—O8167.88 (14)
O3—C4—C5—C6178.45 (15)O5—C7—C12—C11165.34 (15)
C3—C4—C5—C62.6 (2)C8—C7—C12—C1113.2 (2)
O3—C4—C5—Cl23.0 (2)C17—N1—C13—C1455.38 (17)
C3—C4—C5—Cl2175.97 (11)N1—C13—C14—C1556.83 (17)
C4—C5—C6—O4176.08 (15)C13—C14—C15—C20178.69 (13)
Cl2—C5—C6—O42.5 (2)C13—C14—C15—C1655.60 (16)
C4—C5—C6—C15.6 (2)C14—C15—C16—C1755.13 (16)
Cl2—C5—C6—C1175.86 (11)C20—C15—C16—C17178.08 (12)
O1—C1—C6—O48.5 (2)C13—N1—C17—C1654.67 (17)
C2—C1—C6—O4170.67 (14)C15—C16—C17—N155.48 (17)
O1—C1—C6—C5170.03 (15)C22—N2—C18—C1952.57 (17)
C2—C1—C6—C510.8 (2)N2—C18—C19—C2055.52 (17)
O5—C7—C8—C9173.27 (15)C18—C19—C20—C2157.38 (16)
C12—C7—C8—C95.2 (2)C18—C19—C20—C15177.66 (13)
O5—C7—C8—Cl34.5 (2)C14—C15—C20—C19178.13 (12)
C12—C7—C8—Cl3176.98 (11)C16—C15—C20—C1960.84 (16)
C7—C8—C9—O6179.66 (14)C14—C15—C20—C2156.25 (16)
Cl3—C8—C9—O61.9 (2)C16—C15—C20—C21177.29 (12)
C7—C8—C9—C103.4 (2)C19—C20—C21—C2258.14 (16)
Cl3—C8—C9—C10174.37 (11)C15—C20—C21—C22177.44 (12)
O6—C9—C10—O70.2 (2)C18—N2—C22—C2153.18 (17)
C8—C9—C10—O7176.71 (15)C20—C21—C22—N256.98 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O30.87 (3)2.18 (2)2.6479 (16)113.6 (19)
O2—H1···O8i0.87 (3)2.17 (3)2.9113 (18)142 (2)
O6—H2···O3ii0.82 (3)2.12 (3)2.7290 (18)132 (2)
O6—H2···O70.82 (3)2.11 (2)2.6093 (16)119 (2)
N1—H3···O10.90 (2)1.97 (2)2.7921 (19)152 (2)
N1—H3···O3iii0.90 (2)2.48 (2)2.9412 (19)112.7 (17)
N1—H4···O8iv0.86 (2)2.03 (2)2.8269 (17)156 (2)
N2—H14···O50.90 (2)2.15 (2)2.9223 (19)143 (2)
N2—H14···O80.90 (2)2.50 (2)3.200 (2)135.7 (18)
N2—H15···O2i0.88 (2)2.55 (2)3.0332 (18)115.1 (17)
N2—H15···O4v0.88 (2)1.98 (2)2.8158 (18)159 (2)
C14—H7···O10.982.493.211 (2)130
C14—H8···O6vi0.982.483.2561 (19)136
C16—H10···O5vii0.982.593.531 (2)161
C18—H17···O7viii0.982.393.193 (2)138
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z; (iii) x+1/2, y1/2, z+1/2; (iv) x1/2, y+1/2, z1/2; (v) x+1/2, y+1/2, z+1/2; (vi) x+3/2, y1/2, z+1/2; (vii) x, y1, z; (viii) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC10H22N22+·2C6HCl2O4
Mr586.25
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)17.4716 (10), 7.7132 (4), 19.1252 (11)
β (°) 111.5434 (19)
V3)2397.3 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.55
Crystal size (mm)0.25 × 0.17 × 0.12
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.850, 0.937
No. of measured, independent and
observed [I > 2σ(I)] reflections
26002, 6982, 5848
Rint0.035
(sin θ/λ)max1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.088, 1.11
No. of reflections6982
No. of parameters349
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.43, 0.29

Computer programs: PROCESS-AUTO (Rigaku/MSC, 2004), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), CrystalStructure (Rigaku/MSC, 2004) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O30.87 (3)2.18 (2)2.6479 (16)113.6 (19)
O2—H1···O8i0.87 (3)2.17 (3)2.9113 (18)142 (2)
O6—H2···O3ii0.82 (3)2.12 (3)2.7290 (18)132 (2)
O6—H2···O70.82 (3)2.11 (2)2.6093 (16)119 (2)
N1—H3···O10.90 (2)1.97 (2)2.7921 (19)152 (2)
N1—H3···O3iii0.90 (2)2.48 (2)2.9412 (19)112.7 (17)
N1—H4···O8iv0.86 (2)2.03 (2)2.8269 (17)156 (2)
N2—H14···O50.90 (2)2.15 (2)2.9223 (19)143 (2)
N2—H14···O80.90 (2)2.50 (2)3.200 (2)135.7 (18)
N2—H15···O2i0.88 (2)2.55 (2)3.0332 (18)115.1 (17)
N2—H15···O4v0.88 (2)1.98 (2)2.8158 (18)159 (2)
C14—H7···O10.982.493.211 (2)130
C14—H8···O6vi0.982.483.2561 (19)136
C16—H10···O5vii0.982.593.531 (2)161
C18—H17···O7viii0.982.393.193 (2)138
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z; (iii) x+1/2, y1/2, z+1/2; (iv) x1/2, y+1/2, z1/2; (v) x+1/2, y+1/2, z+1/2; (vi) x+3/2, y1/2, z+1/2; (vii) x, y1, z; (viii) x+2, y+1, z+1.
 

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