1-Di­methyl­amino-3-di­methyl­imino-1-phenyl­prop-1-ene perchlorate

The title compound, C₁₃H₁₉N₂⁺·ClO₄⁻, a 1-aryl­ated vinamidinium salt, has been found to crystallize in monoclinic space group P2₁/n at room temperature. The dihedral angle between the planar vinamidinium moiety and the aryl ring is 81.2 (1)°. The molecular packing is stabilized by C—H...O interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.057
• wR factor = 0.204
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C9
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....         C4
PLAT244_ALERT_4_C Low Solvent  U(eq) as Compared to Neighbors ....        Cl1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 1990).

1-Dimethylamino-3-dimethylimino-1-phenylprop-1-ene perchlorate

Crystal data

C13H19N2^+·ClO4^−	F(000) = 640
Mr = 302.75	Dx = 1.289 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yn	Cell parameters from 16 reflections
a = 11.3858 (18) Å	θ = 6.9–7.8°
b = 7.7718 (14) Å	µ = 0.26 mm^−1
c = 18.194 (3) Å	T = 293 K
β = 104.374 (12)°	Prism, colourless
V = 1559.6 (5) Å^3	0.3 × 0.2 × 0.1 mm
Z = 4

Data collection

Rigaku AFC-7S diffractometer	Rint = 0.010
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.3°
Graphite monochromator	h = 0→13
ω/2θ scans	k = 0→9
2899 measured reflections	l = −21→20
2753 independent reflections	3 standard reflections every 150 reflections
1834 reflections with I > 2σ(I)	intensity decay: 0.7%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.204	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.108P)^2 + 0.6901P] where P = (Fo^2 + 2Fc^2)/3
2753 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

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	0.27976 (8)	0.14859 (12)	0.08915 (5)	0.0824 (4)
O1	0.3742 (3)	0.0805 (7)	0.1478 (2)	0.1558 (16)
O2	0.2159 (5)	0.0213 (5)	0.0425 (3)	0.1767 (19)
O3	0.3312 (4)	0.2517 (5)	0.0437 (2)	0.1628 (17)
O4	0.2005 (5)	0.2343 (11)	0.1192 (3)	0.256 (4)
N1	0.7064 (2)	0.2537 (3)	0.08089 (14)	0.0666 (7)
N2	1.0532 (3)	0.6242 (4)	0.12741 (17)	0.0783 (8)
C1	0.8128 (3)	0.3089 (4)	0.12211 (16)	0.0602 (7)
C2	0.8734 (3)	0.4489 (4)	0.10183 (17)	0.0673 (8)
H2	0.8366	0.5115	0.0587	0.081*
C3	0.9869 (3)	0.4983 (4)	0.14375 (18)	0.0704 (8)
H3	1.0196	0.4364	0.1878	0.084*
C4	0.8669 (3)	0.2125 (4)	0.19361 (16)	0.0585 (7)
C5	0.8302 (3)	0.2469 (4)	0.25891 (17)	0.0720 (9)
H5	0.7715	0.3303	0.2586	0.086*
C6	0.8805 (4)	0.1574 (5)	0.32482 (19)	0.0826 (10)
H6	0.8565	0.1823	0.3689	0.099*
C7	0.9650 (3)	0.0329 (5)	0.3256 (2)	0.0795 (10)
H7	0.9981	−0.0273	0.3701	0.095*
C8	1.0006 (4)	−0.0030 (5)	0.2622 (2)	0.0971 (12)
H8	1.0581	−0.0884	0.2630	0.116*
C9	0.9518 (4)	0.0870 (6)	0.1955 (2)	0.0945 (12)
H9	0.9771	0.0617	0.1518	0.113*
C10	0.6450 (3)	0.3364 (5)	0.00944 (19)	0.0857 (10)
H10A	0.6506	0.4591	0.0153	0.128*
H10B	0.5613	0.3028	−0.0041	0.128*
H10C	0.6829	0.3016	−0.0298	0.128*
C11	0.6451 (3)	0.1000 (5)	0.0991 (2)	0.0827 (10)
H11A	0.7036	0.0242	0.1300	0.124*
H11B	0.6054	0.0421	0.0530	0.124*
H11C	0.5861	0.1327	0.1261	0.124*
C12	1.0095 (5)	0.7311 (5)	0.0605 (2)	0.0989 (13)
H12A	0.9340	0.7834	0.0624	0.148*
H12B	0.9978	0.6612	0.0157	0.148*
H12C	1.0681	0.8192	0.0591	0.148*
C13	1.1778 (3)	0.6535 (6)	0.1732 (3)	0.1029 (13)
H13A	1.1897	0.5930	0.2205	0.154*
H13B	1.1903	0.7744	0.1828	0.154*
H13C	1.2344	0.6122	0.1460	0.154*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0796 (6)	0.0741 (6)	0.0949 (7)	−0.0117 (5)	0.0246 (5)	−0.0054 (5)
O1	0.118 (2)	0.212 (4)	0.137 (3)	0.031 (3)	0.033 (2)	0.066 (3)
O2	0.206 (4)	0.113 (3)	0.194 (4)	−0.078 (3)	0.018 (3)	−0.015 (3)
O3	0.164 (3)	0.142 (3)	0.165 (3)	−0.066 (3)	0.008 (3)	0.056 (3)
O4	0.185 (4)	0.387 (9)	0.200 (5)	0.138 (5)	0.056 (4)	−0.075 (6)
N1	0.0699 (15)	0.0665 (15)	0.0594 (14)	−0.0020 (13)	0.0081 (12)	0.0057 (12)
N2	0.0788 (17)	0.0816 (19)	0.0800 (17)	−0.0148 (15)	0.0304 (14)	−0.0082 (15)
C1	0.0656 (17)	0.0594 (17)	0.0579 (16)	0.0061 (14)	0.0194 (13)	0.0001 (14)
C2	0.0757 (19)	0.0669 (18)	0.0607 (17)	−0.0010 (16)	0.0199 (15)	0.0041 (14)
C3	0.074 (2)	0.075 (2)	0.0671 (18)	−0.0005 (17)	0.0273 (16)	−0.0025 (16)
C4	0.0595 (16)	0.0563 (16)	0.0588 (16)	0.0030 (13)	0.0129 (13)	0.0030 (13)
C5	0.087 (2)	0.0653 (19)	0.0616 (18)	0.0169 (17)	0.0152 (16)	0.0007 (15)
C6	0.106 (3)	0.080 (2)	0.0576 (18)	0.005 (2)	0.0136 (18)	0.0006 (17)
C7	0.082 (2)	0.071 (2)	0.073 (2)	0.0018 (18)	−0.0062 (18)	0.0123 (17)
C8	0.095 (3)	0.092 (3)	0.103 (3)	0.040 (2)	0.022 (2)	0.017 (2)
C9	0.104 (3)	0.105 (3)	0.082 (2)	0.039 (2)	0.036 (2)	0.012 (2)
C10	0.089 (2)	0.087 (2)	0.070 (2)	−0.001 (2)	0.0006 (18)	0.0155 (19)
C11	0.083 (2)	0.078 (2)	0.080 (2)	−0.0171 (19)	0.0064 (17)	0.0091 (18)
C12	0.126 (3)	0.081 (3)	0.094 (3)	−0.026 (2)	0.036 (2)	0.005 (2)
C13	0.082 (2)	0.124 (4)	0.107 (3)	−0.025 (2)	0.031 (2)	−0.014 (3)

Geometric parameters (Å, º)

Cl1—O4	1.342 (4)	C6—C7	1.362 (5)
Cl1—O3	1.382 (4)	C6—H6	0.93
Cl1—O2	1.386 (4)	C7—C8	1.343 (5)
Cl1—O1	1.416 (4)	C7—H7	0.93
N1—C1	1.327 (4)	C8—C9	1.393 (5)
N1—C11	1.462 (4)	C8—H8	0.93
N1—C10	1.463 (4)	C9—H9	0.93
N2—C3	1.314 (4)	C10—H10A	0.96
N2—C12	1.456 (5)	C10—H10B	0.96
N2—C13	1.473 (5)	C10—H10C	0.96
C1—C2	1.387 (4)	C11—H11A	0.96
C1—C4	1.495 (4)	C11—H11B	0.96
C2—C3	1.382 (5)	C11—H11C	0.96
C2—H2	0.93	C12—H12A	0.96
C3—H3	0.93	C12—H12B	0.96
C4—C9	1.367 (5)	C12—H12C	0.96
C4—C5	1.380 (4)	C13—H13A	0.96
C5—C6	1.381 (5)	C13—H13B	0.96
C5—H5	0.93	C13—H13C	0.96
O4—Cl1—O3	112.6 (5)	C6—C7—H7	119.9
O4—Cl1—O2	107.5 (4)	C7—C8—C9	120.3 (3)
O3—Cl1—O2	106.5 (3)	C7—C8—H8	119.9
O4—Cl1—O1	109.9 (3)	C9—C8—H8	119.9
O3—Cl1—O1	108.2 (2)	C4—C9—C8	120.4 (3)
O2—Cl1—O1	112.3 (3)	C4—C9—H9	119.8
C1—N1—C11	123.8 (3)	C8—C9—H9	119.8
C1—N1—C10	121.8 (3)	N1—C10—H10A	109.5
C11—N1—C10	114.2 (3)	N1—C10—H10B	109.5
C3—N2—C12	121.2 (3)	H10A—C10—H10B	109.5
C3—N2—C13	120.9 (3)	N1—C10—H10C	109.5
C12—N2—C13	117.7 (3)	H10A—C10—H10C	109.5
N1—C1—C2	123.2 (3)	H10B—C10—H10C	109.5
N1—C1—C4	116.8 (3)	N1—C11—H11A	109.5
C2—C1—C4	120.0 (3)	N1—C11—H11B	109.5
C3—C2—C1	122.0 (3)	H11A—C11—H11B	109.5
C3—C2—H2	119.0	N1—C11—H11C	109.5
C1—C2—H2	119.0	H11A—C11—H11C	109.5
N2—C3—C2	126.4 (3)	H11B—C11—H11C	109.5
N2—C3—H3	116.8	N2—C12—H12A	109.5
C2—C3—H3	116.8	N2—C12—H12B	109.5
C9—C4—C5	118.7 (3)	H12A—C12—H12B	109.5
C9—C4—C1	121.0 (3)	N2—C12—H12C	109.5
C5—C4—C1	120.3 (3)	H12A—C12—H12C	109.5
C4—C5—C6	120.0 (3)	H12B—C12—H12C	109.5
C4—C5—H5	120.0	N2—C13—H13A	109.5
C6—C5—H5	120.0	N2—C13—H13B	109.5
C7—C6—C5	120.4 (3)	H13A—C13—H13B	109.5
C7—C6—H6	119.8	N2—C13—H13C	109.5
C5—C6—H6	119.8	H13A—C13—H13C	109.5
C8—C7—C6	120.1 (3)	H13B—C13—H13C	109.5
C8—C7—H7	119.9
C11—N1—C1—C2	176.0 (3)	N1—C1—C4—C5	−82.0 (4)
C10—N1—C1—C2	0.7 (5)	C2—C1—C4—C5	97.9 (4)
C11—N1—C1—C4	−4.1 (4)	C9—C4—C5—C6	1.1 (5)
C10—N1—C1—C4	−179.4 (3)	C1—C4—C5—C6	−180.0 (3)
N1—C1—C2—C3	−176.6 (3)	C4—C5—C6—C7	−1.1 (5)
C4—C1—C2—C3	3.5 (4)	C5—C6—C7—C8	0.4 (6)
C12—N2—C3—C2	1.2 (5)	C6—C7—C8—C9	0.2 (6)
C13—N2—C3—C2	−174.3 (3)	C5—C4—C9—C8	−0.5 (6)
C1—C2—C3—N2	177.1 (3)	C1—C4—C9—C8	−179.4 (4)
N1—C1—C4—C9	96.8 (4)	C7—C8—C9—C4	−0.2 (7)
C2—C1—C4—C9	−83.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O3^i	0.96	2.52	3.374 (5)	148
C11—H11C···O1	0.96	2.57	3.417 (5)	147
C12—H12C···O2^ii	0.96	2.38	3.331 (7)	173

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