N,N′-Bis(3,4-methyl­enedioxy­benz­yl)propane-1,3-diammonium dichloride

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] 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.

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

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Computing details

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

Crystal data

C19H24N2O4^2+·2Cl^−	Dx = 1.403 Mg m^−3
Mr = 415.30	Melting point: 458 K
Orthorhombic, Pmn21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac -2	Cell parameters from 2090 reflections
a = 38.366 (14) Å	θ = 3.2–27.4°
b = 4.8370 (18) Å	µ = 0.36 mm^−1
c = 5.2980 (19) Å	T = 298 K
V = 983.2 (6) Å^3	Columnar, colourless
Z = 2	0.52 × 0.47 × 0.13 mm
F(000) = 436

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	1725 independent reflections
Radiation source: fine-focus sealed tube	1461 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −43→45
Tmin = 0.836, Tmax = 0.955	k = −5→5
4685 measured reflections	l = −6→5

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.099	w = 1/[σ^2(Fo^2) + (0.0348P)^2 + 0.5461P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
1725 reflections	Δρmax = 0.24 e Å^−3
124 parameters	Δρmin = −0.30 e Å^−3
1 restraint	Absolute structure: Flack (1983), with 736 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.18 (12)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.43820 (2)	0.36226 (17)	0.9267 (2)	0.0406 (2)
N1	0.43522 (5)	0.7032 (4)	0.4240 (8)	0.0273 (5)
H1A	0.4348	0.5852	0.5553	0.033*
H1B	0.4348	0.6025	0.2812	0.033*
O1	0.27780 (6)	0.2955 (6)	0.3395 (6)	0.0563 (8)
O2	0.31331 (6)	0.1937 (6)	0.6786 (6)	0.0541 (7)
C1	0.40351 (7)	0.8822 (7)	0.4332 (10)	0.0352 (7)
H1C	0.4054	1.0235	0.3039	0.042*
H1D	0.4026	0.9744	0.5956	0.042*
C2	0.37005 (7)	0.7231 (7)	0.3941 (7)	0.0294 (8)
C3	0.35983 (8)	0.5243 (7)	0.5705 (7)	0.0343 (8)
H3	0.3738	0.4812	0.7085	0.041*
C4	0.32867 (8)	0.3961 (7)	0.5330 (7)	0.0347 (8)
C5	0.30768 (8)	0.4566 (7)	0.3301 (7)	0.0382 (9)
C6	0.31691 (8)	0.6472 (8)	0.1541 (7)	0.0442 (10)
H6	0.3027	0.6862	0.0162	0.053*
C7	0.34900 (8)	0.7826 (8)	0.1908 (7)	0.0381 (8)
H7	0.3561	0.9155	0.0750	0.046*
C8	0.27921 (10)	0.1605 (10)	0.5783 (9)	0.0599 (13)
H8A	0.2622	0.2408	0.6920	0.072*
H8B	0.2739	−0.0344	0.5586	0.072*
C9	0.46812 (6)	0.8657 (6)	0.4329 (10)	0.0313 (7)
H9A	0.4685	0.9755	0.5861	0.038*
H9B	0.4687	0.9917	0.2905	0.038*
C10	0.5000	0.6846 (8)	0.4261 (14)	0.0311 (10)
H10A	0.5000	0.5740	0.2733	0.037*
H10B	0.5000	0.5605	0.5699	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0510 (5)	0.0423 (4)	0.0284 (4)	0.0026 (4)	−0.0032 (5)	−0.0035 (6)
N1	0.0280 (12)	0.0282 (13)	0.0258 (11)	0.0010 (10)	−0.0007 (14)	−0.002 (2)
O1	0.0353 (14)	0.063 (2)	0.070 (2)	−0.0137 (13)	−0.0063 (13)	0.0014 (17)
O2	0.0387 (13)	0.0577 (18)	0.0658 (17)	−0.0096 (13)	0.0041 (14)	0.0129 (16)
C1	0.0286 (14)	0.0334 (17)	0.0437 (17)	0.0025 (14)	0.000 (2)	−0.006 (2)
C2	0.0258 (14)	0.0333 (17)	0.0292 (19)	0.0060 (13)	0.0048 (15)	−0.0059 (17)
C3	0.0259 (17)	0.041 (2)	0.0364 (18)	0.0066 (15)	−0.0057 (15)	0.0005 (18)
C4	0.0262 (17)	0.0324 (19)	0.045 (2)	0.0053 (15)	0.0068 (16)	0.0001 (17)
C5	0.0225 (17)	0.043 (2)	0.049 (2)	−0.0037 (15)	−0.0004 (16)	−0.0070 (18)
C6	0.0302 (18)	0.062 (3)	0.040 (2)	0.0034 (17)	−0.0073 (16)	−0.002 (2)
C7	0.0357 (18)	0.043 (2)	0.0359 (19)	0.0042 (16)	0.0053 (17)	0.0051 (18)
C8	0.041 (2)	0.059 (3)	0.080 (3)	−0.010 (2)	0.007 (2)	0.000 (3)
C9	0.0289 (15)	0.0303 (16)	0.0347 (15)	−0.0011 (13)	−0.001 (2)	−0.004 (2)
C10	0.030 (2)	0.030 (2)	0.033 (2)	0.000	0.000	−0.004 (3)

Geometric parameters (Å, º)

N1—C9	1.488 (3)	C3—H3	0.9300
N1—C1	1.494 (3)	C4—C5	1.375 (5)
N1—H1A	0.9000	C5—C6	1.358 (5)
N1—H1B	0.9000	C6—C7	1.408 (5)
O1—C5	1.387 (4)	C6—H6	0.9300
O1—C8	1.425 (5)	C7—H7	0.9300
O2—C4	1.379 (4)	C8—H8A	0.9700
O2—C8	1.422 (5)	C8—H8B	0.9700
C1—C2	1.511 (4)	C9—C10	1.505 (4)
C1—H1C	0.9700	C9—H9A	0.9700
C1—H1D	0.9700	C9—H9B	0.9700
C2—C7	1.376 (5)	C10—C9^i	1.505 (4)
C2—C3	1.397 (5)	C10—H10A	0.9700
C3—C4	1.361 (5)	C10—H10B	0.9700
C9—N1—C1	112.6 (2)	C4—C5—O1	109.7 (3)
C9—N1—H1A	109.1	C5—C6—C7	116.7 (3)
C1—N1—H1A	109.1	C5—C6—H6	121.7
C9—N1—H1B	109.1	C7—C6—H6	121.7
C1—N1—H1B	109.1	C2—C7—C6	121.6 (3)
H1A—N1—H1B	107.8	C2—C7—H7	119.2
C5—O1—C8	105.0 (3)	C6—C7—H7	119.2
C4—O2—C8	105.3 (3)	O2—C8—O1	108.4 (3)
N1—C1—C2	113.1 (3)	O2—C8—H8A	110.0
N1—C1—H1C	109.0	O1—C8—H8A	110.0
C2—C1—H1C	109.0	O2—C8—H8B	110.0
N1—C1—H1D	109.0	O1—C8—H8B	110.0
C2—C1—H1D	109.0	H8A—C8—H8B	108.4
H1C—C1—H1D	107.8	N1—C9—C10	112.4 (2)
C7—C2—C3	120.2 (3)	N1—C9—H9A	109.1
C7—C2—C1	119.9 (3)	C10—C9—H9A	109.1
C3—C2—C1	119.8 (3)	N1—C9—H9B	109.1
C4—C3—C2	117.5 (3)	C10—C9—H9B	109.1
C4—C3—H3	121.2	H9A—C9—H9B	107.9
C2—C3—H3	121.2	C9—C10—C9^i	108.7 (3)
C3—C4—C5	122.1 (3)	C9—C10—H10A	109.9
C3—C4—O2	128.1 (3)	C9^i—C10—H10A	109.9
C5—C4—O2	109.8 (3)	C9—C10—H10B	109.9
C6—C5—C4	121.9 (3)	C9^i—C10—H10B	109.9
C6—C5—O1	128.4 (3)	H10A—C10—H10B	108.3
C9—N1—C1—C2	173.3 (3)	O2—C4—C5—O1	0.4 (4)
N1—C1—C2—C7	−118.3 (4)	C8—O1—C5—C6	−172.5 (4)
N1—C1—C2—C3	64.5 (5)	C8—O1—C5—C4	8.0 (4)
C7—C2—C3—C4	−0.2 (5)	C4—C5—C6—C7	−0.7 (5)
C1—C2—C3—C4	176.9 (3)	O1—C5—C6—C7	179.9 (3)
C2—C3—C4—C5	0.1 (5)	C3—C2—C7—C6	−0.1 (5)
C2—C3—C4—O2	179.5 (3)	C1—C2—C7—C6	−177.2 (3)
C8—O2—C4—C3	171.9 (4)	C5—C6—C7—C2	0.5 (5)
C8—O2—C4—C5	−8.7 (4)	C4—O2—C8—O1	13.6 (4)
C3—C4—C5—C6	0.4 (5)	C5—O1—C8—O2	−13.3 (4)
O2—C4—C5—C6	−179.1 (3)	C1—N1—C9—C10	179.5 (4)
C3—C4—C5—O1	179.9 (3)	N1—C9—C10—C9^i	179.4 (3)

Symmetry code: (i) −x+1, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	0.90	2.25	3.134 (4)	169
C3—H3···Cl1	0.93	2.79	3.636 (3)	152
N1—H1B···Cl1^ii	0.90	2.21	3.111 (4)	176
C1—H1D···Cl1^iii	0.97	2.91	3.742 (4)	145
C9—H9A···Cl1^iii	0.97	2.85	3.732 (4)	152
C1—H1C···Cl1^iv	0.97	2.87	3.790 (5)	158
C9—H9B···Cl1^iv	0.97	2.88	3.779 (5)	154

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