N,N'-Bis­(amino­propyl)-1,4-benzyl­idenedi­ammonium diperchlorate

The structure determination of the title compound, [C₁₄H₂₄N₄](ClO₄)₂, indicates that intermolecular hydrogen bonds between the N atom of the amino­propyl group and an O atom of the perchlorate result in a two-dimensional layer structure. The cation has crystallographic inversion symmetry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.049
• wR factor = 0.138
• Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.92

Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O1     ..  O2       =       2.83 Ang.

Alert level C
WEIGH01_ALERT_1_C  Extra text has been found in the
            _refine_ls_weighting_scheme field. This should be in the
            _refine_ls_weighting_details field.
            Weighting scheme given as calc w = 1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.8221
            Weighting scheme identified as calc
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.18
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        Cl1

   1 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Blessing, 1995); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1997a); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXL97.

N,N'-Bis(aminopropyl)-1,4-benzylidenediammonium diperchlorate

Crystal data

C14H24N4^2+·2ClO4^−	F(000) = 468
Mr = 447.27	Dx = 1.519 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.358 (3) Å	Cell parameters from 4254 reflections
b = 7.864 (2) Å	θ = 3.1–52.0°
c = 9.313 (2) Å	µ = 0.38 mm^−1
β = 91.714 (3)°	T = 293 K
V = 977.9 (4) Å^3	Block, colourless
Z = 2	0.38 × 0.16 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1915 independent reflections
Radiation source: fine-focus sealed tube	1691 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −16→16
Tmin = 0.868, Tmax = 0.941	k = −9→4
4254 measured reflections	l = −10→11

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.138	Calculated w = 1/[σ^2(Fo^2) + (0.0709P)^2 + 0.8221P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1915 reflections	Δρmax = 0.63 e Å^−3
128 parameters	Δρmin = −0.29 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.035 (4)

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
N1	0.15125 (17)	0.9734 (4)	0.1722 (3)	0.0627 (7)
N2	0.36637 (15)	0.9651 (3)	0.2013 (2)	0.0435 (5)
H2A	0.3072	0.9985	0.2325	0.065*
H2B	0.4118	1.0454	0.2202	0.065*
H2C	0.3847	0.8692	0.2455	0.065*
C1	−0.09545 (19)	0.9521 (4)	0.5346 (4)	0.0582 (7)
H1	−0.1600	0.9201	0.5576	0.070*
C2	−0.06226 (19)	0.9220 (4)	0.4008 (3)	0.0575 (7)
H2	−0.1044	0.8686	0.3335	0.069*
C3	0.03356 (18)	0.9694 (4)	0.3621 (3)	0.0537 (7)
C4	0.0655 (2)	0.9377 (4)	0.2165 (3)	0.0585 (7)
H4	0.0198	0.8879	0.1520	0.070*
C5	0.1703 (2)	0.9453 (5)	0.0204 (4)	0.0683 (9)
H5A	0.1755	1.0543	−0.0275	0.082*
H5B	0.1141	0.8844	−0.0235	0.082*
C6	0.2626 (2)	0.8476 (5)	−0.0004 (4)	0.0647 (8)
H6A	0.2659	0.8183	−0.1013	0.078*
H6B	0.2582	0.7421	0.0530	0.078*
C7	0.35874 (19)	0.9355 (4)	0.0444 (3)	0.0481 (6)
H7A	0.4150	0.8665	0.0158	0.058*
H7B	0.3626	1.0437	−0.0051	0.058*
Cl1	0.37926 (4)	0.08558 (7)	0.63657 (6)	0.0425 (3)
O1	0.40930 (18)	−0.0678 (3)	0.7055 (3)	0.0689 (6)
O2	0.46099 (15)	0.2022 (3)	0.6485 (3)	0.0726 (7)
O3	0.3546 (2)	0.0555 (4)	0.4919 (2)	0.0809 (7)
O4	0.29587 (16)	0.1582 (3)	0.7040 (3)	0.0764 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0390 (12)	0.0830 (18)	0.0659 (15)	0.0021 (12)	−0.0036 (10)	−0.0157 (14)
N2	0.0393 (10)	0.0483 (11)	0.0426 (11)	−0.0014 (9)	−0.0015 (8)	0.0055 (9)
C1	0.0298 (12)	0.0691 (18)	0.0756 (19)	−0.0033 (12)	−0.0020 (12)	−0.0097 (15)
C2	0.0322 (12)	0.0687 (19)	0.0711 (19)	−0.0027 (11)	−0.0068 (12)	−0.0125 (14)
C3	0.0317 (12)	0.0576 (16)	0.0713 (18)	0.0039 (11)	−0.0062 (11)	−0.0060 (14)
C4	0.0359 (13)	0.0688 (19)	0.0701 (18)	0.0019 (12)	−0.0087 (12)	−0.0108 (15)
C5	0.0551 (17)	0.087 (2)	0.0624 (18)	0.0048 (16)	−0.0076 (14)	−0.0087 (17)
C6	0.0576 (17)	0.074 (2)	0.0620 (18)	−0.0002 (15)	−0.0039 (13)	−0.0162 (15)
C7	0.0461 (14)	0.0540 (15)	0.0444 (14)	−0.0020 (11)	0.0058 (10)	−0.0055 (11)
Cl1	0.0411 (4)	0.0425 (4)	0.0435 (4)	0.0006 (2)	−0.0085 (2)	−0.0019 (2)
O1	0.0823 (15)	0.0526 (12)	0.0709 (14)	0.0034 (10)	−0.0095 (11)	0.0129 (10)
O2	0.0449 (11)	0.0527 (12)	0.1192 (19)	−0.0040 (9)	−0.0140 (11)	−0.0057 (12)
O3	0.0906 (17)	0.1066 (19)	0.0444 (12)	−0.0045 (14)	−0.0160 (11)	−0.0008 (12)
O4	0.0504 (12)	0.0854 (17)	0.0937 (17)	0.0067 (12)	0.0065 (11)	−0.0164 (14)

Geometric parameters (Å, º)

N1—C4	1.261 (4)	C4—H4	0.9300
N1—C5	1.460 (4)	C5—C6	1.471 (4)
N2—C7	1.480 (3)	C5—H5A	0.9700
N2—H2A	0.8900	C5—H5B	0.9700
N2—H2B	0.8900	C6—C7	1.506 (4)
N2—H2C	0.8900	C6—H6A	0.9701
C1—C2	1.356 (4)	C6—H6B	0.9700
C1—C3^i	1.394 (4)	C7—H7A	0.9700
C1—H1	0.9300	C7—H7B	0.9700
C2—C3	1.391 (4)	Cl1—O3	1.397 (2)
C2—H2	0.9300	Cl1—O4	1.415 (2)
C3—C1^i	1.394 (4)	Cl1—O1	1.419 (2)
C3—C4	1.456 (4)	Cl1—O2	1.427 (2)
C4—N1—C5	118.0 (3)	N1—C5—H5B	109.2
C7—N2—H2A	109.5	C6—C5—H5B	109.2
C7—N2—H2B	109.5	H5A—C5—H5B	107.9
H2A—N2—H2B	109.5	C5—C6—C7	115.8 (3)
C7—N2—H2C	109.5	C5—C6—H6A	108.3
H2A—N2—H2C	109.5	C7—C6—H6A	108.3
H2B—N2—H2C	109.5	C5—C6—H6B	108.3
C2—C1—C3^i	120.5 (3)	C7—C6—H6B	108.3
C2—C1—H1	119.7	H6A—C6—H6B	107.4
C3^i—C1—H1	119.7	N2—C7—C6	112.3 (2)
C1—C2—C3	121.3 (3)	N2—C7—H7A	109.2
C1—C2—H2	119.3	C6—C7—H7A	109.1
C3—C2—H2	119.3	N2—C7—H7B	109.2
C2—C3—C1^i	118.2 (3)	C6—C7—H7B	109.1
C2—C3—C4	119.5 (3)	H7A—C7—H7B	107.9
C1^i—C3—C4	122.3 (3)	O3—Cl1—O4	109.27 (15)
N1—C4—C3	124.2 (3)	O3—Cl1—O1	110.32 (15)
N1—C4—H4	117.9	O4—Cl1—O1	110.99 (16)
C3—C4—H4	117.9	O3—Cl1—O2	109.99 (16)
N1—C5—C6	112.2 (3)	O4—Cl1—O2	108.44 (14)
N1—C5—H5A	109.2	O1—Cl1—O2	107.79 (14)
C6—C5—H5A	109.2
C3^i—C1—C2—C3	−0.5 (5)	C1^i—C3—C4—N1	1.9 (5)
C1—C2—C3—C1^i	0.5 (5)	C4—N1—C5—C6	−129.8 (3)
C1—C2—C3—C4	−178.8 (3)	N1—C5—C6—C7	−66.6 (4)
C5—N1—C4—C3	−175.8 (3)	C5—C6—C7—N2	65.6 (4)
C2—C3—C4—N1	−178.8 (3)

Symmetry code: (i) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2C···O1^ii	0.89	2.42	3.176 (3)	143
N2—H2C···O2^iii	0.89	2.33	2.968 (3)	129
N2—H2B···O1^iii	0.89	2.47	3.199 (3)	139
N2—H2B···O2^iv	0.89	2.20	2.953 (3)	142
N2—H2A···N1	0.89	2.15	2.879 (3)	139

Symmetry codes: (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z+1; (iv) x, −y+3/2, z−1/2.