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In the title compound, C19H24N2O42+·2Cl, the cation has mirror symmetry. The ions are linked by N—H...Cl and C—H...Cl hydrogen bonds into a [01\overline{1}] chain with an S21(7)S21(7)R42(14)[R42(24)] motif, and into a [011] chain with an S21(7)R42(14)[R42(18)] motif.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806053554/at2186sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806053554/at2186Isup2.hkl
Contains datablock I

CCDC reference: 628483

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.099
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H1D .. CL1 .. 2.91 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9A .. CL1 .. 2.85 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1C .. CL1 .. 2.87 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H9B .. CL1 .. 2.88 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 1725 Count of symmetry unique reflns 989 Completeness (_total/calc) 174.42% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 736 Fraction of Friedel pairs measured 0.744 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 5 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

N,N'-Bis(3,4-methylenedioxybenzyl)propane-1,3-diammonium dichloride top
Crystal data top
C19H24N2O42+·2ClDx = 1.403 Mg m3
Mr = 415.30Melting point: 458 K
Orthorhombic, Pmn21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac -2Cell parameters from 2090 reflections
a = 38.366 (14) Åθ = 3.2–27.4°
b = 4.8370 (18) ŵ = 0.36 mm1
c = 5.2980 (19) ÅT = 298 K
V = 983.2 (6) Å3Columnar, colourless
Z = 20.52 × 0.47 × 0.13 mm
F(000) = 436
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
1725 independent reflections
Radiation source: fine-focus sealed tube1461 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 4345
Tmin = 0.836, Tmax = 0.955k = 55
4685 measured reflectionsl = 65
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.0348P)2 + 0.5461P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
1725 reflectionsΔρmax = 0.24 e Å3
124 parametersΔρmin = 0.30 e Å3
1 restraintAbsolute structure: Flack (1983), with 736 Freidel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.18 (12)
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
Cl10.43820 (2)0.36226 (17)0.9267 (2)0.0406 (2)
N10.43522 (5)0.7032 (4)0.4240 (8)0.0273 (5)
H1A0.43480.58520.55530.033*
H1B0.43480.60250.28120.033*
O10.27780 (6)0.2955 (6)0.3395 (6)0.0563 (8)
O20.31331 (6)0.1937 (6)0.6786 (6)0.0541 (7)
C10.40351 (7)0.8822 (7)0.4332 (10)0.0352 (7)
H1C0.40541.02350.30390.042*
H1D0.40260.97440.59560.042*
C20.37005 (7)0.7231 (7)0.3941 (7)0.0294 (8)
C30.35983 (8)0.5243 (7)0.5705 (7)0.0343 (8)
H30.37380.48120.70850.041*
C40.32867 (8)0.3961 (7)0.5330 (7)0.0347 (8)
C50.30768 (8)0.4566 (7)0.3301 (7)0.0382 (9)
C60.31691 (8)0.6472 (8)0.1541 (7)0.0442 (10)
H60.30270.68620.01620.053*
C70.34900 (8)0.7826 (8)0.1908 (7)0.0381 (8)
H70.35610.91550.07500.046*
C80.27921 (10)0.1605 (10)0.5783 (9)0.0599 (13)
H8A0.26220.24080.69200.072*
H8B0.27390.03440.55860.072*
C90.46812 (6)0.8657 (6)0.4329 (10)0.0313 (7)
H9A0.46850.97550.58610.038*
H9B0.46870.99170.29050.038*
C100.50000.6846 (8)0.4261 (14)0.0311 (10)
H10A0.50000.57400.27330.037*
H10B0.50000.56050.56990.037*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0510 (5)0.0423 (4)0.0284 (4)0.0026 (4)0.0032 (5)0.0035 (6)
N10.0280 (12)0.0282 (13)0.0258 (11)0.0010 (10)0.0007 (14)0.002 (2)
O10.0353 (14)0.063 (2)0.070 (2)0.0137 (13)0.0063 (13)0.0014 (17)
O20.0387 (13)0.0577 (18)0.0658 (17)0.0096 (13)0.0041 (14)0.0129 (16)
C10.0286 (14)0.0334 (17)0.0437 (17)0.0025 (14)0.000 (2)0.006 (2)
C20.0258 (14)0.0333 (17)0.0292 (19)0.0060 (13)0.0048 (15)0.0059 (17)
C30.0259 (17)0.041 (2)0.0364 (18)0.0066 (15)0.0057 (15)0.0005 (18)
C40.0262 (17)0.0324 (19)0.045 (2)0.0053 (15)0.0068 (16)0.0001 (17)
C50.0225 (17)0.043 (2)0.049 (2)0.0037 (15)0.0004 (16)0.0070 (18)
C60.0302 (18)0.062 (3)0.040 (2)0.0034 (17)0.0073 (16)0.002 (2)
C70.0357 (18)0.043 (2)0.0359 (19)0.0042 (16)0.0053 (17)0.0051 (18)
C80.041 (2)0.059 (3)0.080 (3)0.010 (2)0.007 (2)0.000 (3)
C90.0289 (15)0.0303 (16)0.0347 (15)0.0011 (13)0.001 (2)0.004 (2)
C100.030 (2)0.030 (2)0.033 (2)0.0000.0000.004 (3)
Geometric parameters (Å, º) top
N1—C91.488 (3)C3—H30.9300
N1—C11.494 (3)C4—C51.375 (5)
N1—H1A0.9000C5—C61.358 (5)
N1—H1B0.9000C6—C71.408 (5)
O1—C51.387 (4)C6—H60.9300
O1—C81.425 (5)C7—H70.9300
O2—C41.379 (4)C8—H8A0.9700
O2—C81.422 (5)C8—H8B0.9700
C1—C21.511 (4)C9—C101.505 (4)
C1—H1C0.9700C9—H9A0.9700
C1—H1D0.9700C9—H9B0.9700
C2—C71.376 (5)C10—C9i1.505 (4)
C2—C31.397 (5)C10—H10A0.9700
C3—C41.361 (5)C10—H10B0.9700
C9—N1—C1112.6 (2)C4—C5—O1109.7 (3)
C9—N1—H1A109.1C5—C6—C7116.7 (3)
C1—N1—H1A109.1C5—C6—H6121.7
C9—N1—H1B109.1C7—C6—H6121.7
C1—N1—H1B109.1C2—C7—C6121.6 (3)
H1A—N1—H1B107.8C2—C7—H7119.2
C5—O1—C8105.0 (3)C6—C7—H7119.2
C4—O2—C8105.3 (3)O2—C8—O1108.4 (3)
N1—C1—C2113.1 (3)O2—C8—H8A110.0
N1—C1—H1C109.0O1—C8—H8A110.0
C2—C1—H1C109.0O2—C8—H8B110.0
N1—C1—H1D109.0O1—C8—H8B110.0
C2—C1—H1D109.0H8A—C8—H8B108.4
H1C—C1—H1D107.8N1—C9—C10112.4 (2)
C7—C2—C3120.2 (3)N1—C9—H9A109.1
C7—C2—C1119.9 (3)C10—C9—H9A109.1
C3—C2—C1119.8 (3)N1—C9—H9B109.1
C4—C3—C2117.5 (3)C10—C9—H9B109.1
C4—C3—H3121.2H9A—C9—H9B107.9
C2—C3—H3121.2C9—C10—C9i108.7 (3)
C3—C4—C5122.1 (3)C9—C10—H10A109.9
C3—C4—O2128.1 (3)C9i—C10—H10A109.9
C5—C4—O2109.8 (3)C9—C10—H10B109.9
C6—C5—C4121.9 (3)C9i—C10—H10B109.9
C6—C5—O1128.4 (3)H10A—C10—H10B108.3
C9—N1—C1—C2173.3 (3)O2—C4—C5—O10.4 (4)
N1—C1—C2—C7118.3 (4)C8—O1—C5—C6172.5 (4)
N1—C1—C2—C364.5 (5)C8—O1—C5—C48.0 (4)
C7—C2—C3—C40.2 (5)C4—C5—C6—C70.7 (5)
C1—C2—C3—C4176.9 (3)O1—C5—C6—C7179.9 (3)
C2—C3—C4—C50.1 (5)C3—C2—C7—C60.1 (5)
C2—C3—C4—O2179.5 (3)C1—C2—C7—C6177.2 (3)
C8—O2—C4—C3171.9 (4)C5—C6—C7—C20.5 (5)
C8—O2—C4—C58.7 (4)C4—O2—C8—O113.6 (4)
C3—C4—C5—C60.4 (5)C5—O1—C8—O213.3 (4)
O2—C4—C5—C6179.1 (3)C1—N1—C9—C10179.5 (4)
C3—C4—C5—O1179.9 (3)N1—C9—C10—C9i179.4 (3)
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl10.902.253.134 (4)169
C3—H3···Cl10.932.793.636 (3)152
N1—H1B···Cl1ii0.902.213.111 (4)176
C1—H1D···Cl1iii0.972.913.742 (4)145
C9—H9A···Cl1iii0.972.853.732 (4)152
C1—H1C···Cl1iv0.972.873.790 (5)158
C9—H9B···Cl1iv0.972.883.779 (5)154
Symmetry codes: (ii) x, y, z1; (iii) x, y+1, z; (iv) x, y+1, z1.
 

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