The title compound, C
14H
21N
2O
+·ClO
4−, a methoxy-1-arylated vinamidinium salt, has been found to crystallize in the monoclinic space group
P2
1/
c at room temperature. The vinamidinium plane forms a dihedral angle of 61.2 (1)° with the benzene ring. The molecular packing is stabilized by C—H
O interactions.
Supporting information
CCDC reference: 224412
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.148
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91
Alert level B
PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg.
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 24.99
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 2632
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 2900
Completeness (_total/calc) 90.76%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91
PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .... Cl
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
3 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
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: DIRDIF96 (Beurskens et al., 1999); 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-dimethyliminio-1-(
p-methoxyphenyl)prop-1-ene
perchlorate
top
Crystal data top
C14H21N2O+·ClO4− | F(000) = 704 |
Mr = 332.78 | Dx = 1.342 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 15 reflections |
a = 8.239 (3) Å | θ = 6.9–8.0° |
b = 12.399 (2) Å | µ = 0.26 mm−1 |
c = 16.152 (3) Å | T = 293 K |
β = 93.10 (2)° | Prism, colourless |
V = 1647.5 (7) Å3 | 0.3 × 0.2 × 0.1 mm |
Z = 4 | |
Data collection top
Rigaku AFC-7S diffractometer | Rint = 0.033 |
Radiation source: fine focus sealed tube | θmax = 25.0°, θmin = 2.1° |
Graphite monochromator | h = 0→8 |
ω–2θ scans | k = 0→14 |
4573 measured reflections | l = −19→19 |
2632 independent reflections | 3 standard reflections every 150 reflections |
2165 reflections with I > 2σ(I) | intensity decay: −2.9% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0694P)2 + 1.1572P] where P = (Fo2 + 2Fc2)/3 |
2632 reflections | (Δ/σ)max < 0.001 |
204 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.41 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl | 0.72695 (10) | 0.31905 (6) | 0.39881 (4) | 0.0600 (3) | |
O1 | 0.5710 (4) | 0.2722 (4) | 0.4108 (2) | 0.1301 (13) | |
O2 | 0.8148 (3) | 0.3136 (2) | 0.47693 (16) | 0.0924 (9) | |
O3 | 0.7067 (7) | 0.4225 (3) | 0.3712 (3) | 0.180 (2) | |
O4 | 0.8005 (4) | 0.2541 (3) | 0.34001 (16) | 0.1127 (11) | |
O5 | 0.1412 (3) | 0.51292 (16) | −0.12847 (11) | 0.0585 (5) | |
N1 | 0.3821 (3) | 0.20799 (18) | 0.16951 (13) | 0.0504 (6) | |
N2 | 0.1457 (3) | 0.49010 (19) | 0.32478 (13) | 0.0544 (6) | |
C1 | 0.3109 (3) | 0.3041 (2) | 0.17392 (16) | 0.0439 (6) | |
C2 | 0.2743 (4) | 0.3489 (2) | 0.25039 (16) | 0.0510 (7) | |
H2 | 0.3137 | 0.3156 | 0.2990 | 0.061* | |
C3 | 0.1820 (3) | 0.4407 (2) | 0.25574 (16) | 0.0495 (7) | |
H3 | 0.1413 | 0.4708 | 0.2061 | 0.059* | |
C4 | 0.2676 (3) | 0.3615 (2) | 0.09501 (15) | 0.0416 (6) | |
C5 | 0.3253 (3) | 0.4644 (2) | 0.08034 (16) | 0.0471 (6) | |
H5 | 0.3919 | 0.4982 | 0.1208 | 0.057* | |
C6 | 0.2859 (3) | 0.5181 (2) | 0.00675 (16) | 0.0478 (6) | |
H6 | 0.3262 | 0.5870 | −0.0021 | 0.057* | |
C7 | 0.1863 (3) | 0.4684 (2) | −0.05329 (15) | 0.0443 (6) | |
C8 | 0.1236 (3) | 0.3666 (2) | −0.03908 (16) | 0.0488 (6) | |
H8 | 0.0541 | 0.3340 | −0.0789 | 0.059* | |
C9 | 0.1645 (3) | 0.3139 (2) | 0.03425 (16) | 0.0478 (6) | |
H9 | 0.1226 | 0.2455 | 0.0433 | 0.057* | |
C10 | 0.4131 (5) | 0.1397 (2) | 0.2427 (2) | 0.0683 (9) | |
H10A | 0.3215 | 0.1429 | 0.2770 | 0.102* | |
H10B | 0.5084 | 0.1649 | 0.2736 | 0.102* | |
H10C | 0.4296 | 0.0666 | 0.2255 | 0.102* | |
C11 | 0.4583 (4) | 0.1683 (3) | 0.0951 (2) | 0.0655 (8) | |
H11A | 0.4498 | 0.2223 | 0.0526 | 0.098* | |
H11B | 0.4041 | 0.1038 | 0.0758 | 0.098* | |
H11C | 0.5709 | 0.1527 | 0.1085 | 0.098* | |
C12 | 0.1999 (5) | 0.4485 (3) | 0.40635 (17) | 0.0697 (9) | |
H12A | 0.3135 | 0.4313 | 0.4067 | 0.105* | |
H12B | 0.1393 | 0.3847 | 0.4182 | 0.105* | |
H12C | 0.1823 | 0.5022 | 0.4478 | 0.105* | |
C13 | 0.0405 (5) | 0.5848 (3) | 0.3225 (2) | 0.0746 (10) | |
H13A | 0.0196 | 0.6073 | 0.2661 | 0.112* | |
H13B | 0.0930 | 0.6422 | 0.3536 | 0.112* | |
H13C | −0.0604 | 0.5672 | 0.3464 | 0.112* | |
C14 | 0.2051 (4) | 0.6161 (3) | −0.1474 (2) | 0.0688 (9) | |
H14A | 0.1582 | 0.6402 | −0.1999 | 0.103* | |
H14B | 0.3210 | 0.6112 | −0.1502 | 0.103* | |
H14C | 0.1794 | 0.6666 | −0.1050 | 0.103* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl | 0.0657 (5) | 0.0604 (5) | 0.0537 (4) | 0.0127 (4) | 0.0013 (3) | 0.0058 (3) |
O1 | 0.087 (2) | 0.214 (4) | 0.089 (2) | −0.026 (2) | 0.0046 (16) | −0.010 (2) |
O2 | 0.0962 (19) | 0.108 (2) | 0.0695 (15) | 0.0219 (16) | −0.0216 (14) | −0.0145 (14) |
O3 | 0.288 (6) | 0.080 (2) | 0.171 (4) | 0.053 (3) | −0.005 (4) | 0.044 (2) |
O4 | 0.132 (3) | 0.144 (3) | 0.0633 (15) | 0.055 (2) | 0.0152 (16) | −0.0091 (17) |
O5 | 0.0718 (14) | 0.0573 (11) | 0.0456 (10) | −0.0043 (10) | −0.0039 (9) | 0.0096 (9) |
N1 | 0.0591 (15) | 0.0466 (12) | 0.0452 (12) | 0.0034 (11) | −0.0012 (10) | −0.0018 (9) |
N2 | 0.0671 (16) | 0.0539 (13) | 0.0424 (12) | 0.0046 (12) | 0.0033 (11) | −0.0047 (10) |
C1 | 0.0432 (15) | 0.0442 (14) | 0.0440 (14) | −0.0030 (11) | −0.0018 (11) | −0.0019 (10) |
C2 | 0.0637 (18) | 0.0514 (15) | 0.0371 (13) | 0.0050 (14) | −0.0039 (12) | 0.0010 (11) |
C3 | 0.0554 (17) | 0.0526 (15) | 0.0401 (14) | 0.0012 (13) | −0.0002 (12) | −0.0024 (11) |
C4 | 0.0428 (14) | 0.0439 (13) | 0.0386 (12) | 0.0003 (11) | 0.0060 (11) | −0.0025 (10) |
C5 | 0.0494 (16) | 0.0470 (14) | 0.0447 (14) | −0.0040 (12) | −0.0009 (12) | −0.0055 (11) |
C6 | 0.0528 (16) | 0.0417 (13) | 0.0491 (14) | −0.0050 (12) | 0.0050 (12) | 0.0000 (11) |
C7 | 0.0466 (15) | 0.0472 (14) | 0.0393 (13) | 0.0052 (12) | 0.0053 (11) | 0.0014 (11) |
C8 | 0.0545 (17) | 0.0500 (15) | 0.0414 (13) | −0.0072 (13) | −0.0028 (12) | −0.0035 (11) |
C9 | 0.0564 (17) | 0.0427 (14) | 0.0443 (14) | −0.0083 (12) | 0.0043 (12) | −0.0022 (11) |
C10 | 0.092 (2) | 0.0489 (16) | 0.0614 (18) | 0.0087 (17) | −0.0156 (17) | 0.0060 (14) |
C11 | 0.071 (2) | 0.0595 (18) | 0.0668 (19) | 0.0134 (16) | 0.0138 (16) | −0.0082 (15) |
C12 | 0.101 (3) | 0.067 (2) | 0.0418 (15) | 0.0055 (18) | 0.0053 (16) | −0.0034 (13) |
C13 | 0.088 (3) | 0.066 (2) | 0.069 (2) | 0.0192 (18) | 0.0057 (18) | −0.0123 (16) |
C14 | 0.083 (2) | 0.0607 (19) | 0.0623 (18) | −0.0022 (17) | 0.0047 (17) | 0.0194 (15) |
Geometric parameters (Å, º) top
Cl—O3 | 1.365 (3) | C6—C7 | 1.381 (4) |
Cl—O4 | 1.407 (3) | C6—H6 | 0.93 |
Cl—O2 | 1.422 (3) | C7—C8 | 1.388 (4) |
Cl—O1 | 1.432 (3) | C8—C9 | 1.379 (4) |
O5—C7 | 1.367 (3) | C8—H8 | 0.93 |
O5—C14 | 1.423 (4) | C9—H9 | 0.93 |
N1—C1 | 1.332 (3) | C10—H10A | 0.96 |
N1—C10 | 1.466 (4) | C10—H10B | 0.96 |
N1—C11 | 1.470 (4) | C10—H10C | 0.96 |
N2—C3 | 1.321 (3) | C11—H11A | 0.96 |
N2—C13 | 1.459 (4) | C11—H11B | 0.96 |
N2—C12 | 1.462 (4) | C11—H11C | 0.96 |
C1—C2 | 1.402 (4) | C12—H12A | 0.96 |
C1—C4 | 1.486 (3) | C12—H12B | 0.96 |
C2—C3 | 1.374 (4) | C12—H12C | 0.96 |
C2—H2 | 0.93 | C13—H13A | 0.96 |
C3—H3 | 0.93 | C13—H13B | 0.96 |
C4—C5 | 1.386 (4) | C13—H13C | 0.96 |
C4—C9 | 1.394 (4) | C14—H14A | 0.96 |
C5—C6 | 1.386 (4) | C14—H14B | 0.96 |
C5—H5 | 0.93 | C14—H14C | 0.96 |
| | | |
O3—Cl—O4 | 111.5 (3) | C9—C8—H8 | 120.1 |
O3—Cl—O2 | 112.4 (3) | C7—C8—H8 | 120.1 |
O4—Cl—O2 | 110.77 (17) | C8—C9—C4 | 121.0 (2) |
O3—Cl—O1 | 109.3 (3) | C8—C9—H9 | 119.5 |
O4—Cl—O1 | 106.3 (2) | C4—C9—H9 | 119.5 |
O2—Cl—O1 | 106.16 (19) | N1—C10—H10A | 109.5 |
C7—O5—C14 | 117.9 (2) | N1—C10—H10B | 109.5 |
C1—N1—C10 | 122.1 (2) | H10A—C10—H10B | 109.5 |
C1—N1—C11 | 123.5 (2) | N1—C10—H10C | 109.5 |
C10—N1—C11 | 113.7 (2) | H10A—C10—H10C | 109.5 |
C3—N2—C13 | 120.9 (3) | H10B—C10—H10C | 109.5 |
C3—N2—C12 | 121.7 (2) | N1—C11—H11A | 109.5 |
C13—N2—C12 | 117.3 (2) | N1—C11—H11B | 109.5 |
N1—C1—C2 | 121.2 (2) | H11A—C11—H11B | 109.5 |
N1—C1—C4 | 118.0 (2) | N1—C11—H11C | 109.5 |
C2—C1—C4 | 120.8 (2) | H11A—C11—H11C | 109.5 |
C3—C2—C1 | 122.0 (2) | H11B—C11—H11C | 109.5 |
C3—C2—H2 | 119.0 | N2—C12—H12A | 109.5 |
C1—C2—H2 | 119.0 | N2—C12—H12B | 109.5 |
N2—C3—C2 | 126.1 (3) | H12A—C12—H12B | 109.5 |
N2—C3—H3 | 117.0 | N2—C12—H12C | 109.5 |
C2—C3—H3 | 117.0 | H12A—C12—H12C | 109.5 |
C5—C4—C9 | 118.1 (2) | H12B—C12—H12C | 109.5 |
C5—C4—C1 | 121.3 (2) | N2—C13—H13A | 109.5 |
C9—C4—C1 | 120.6 (2) | N2—C13—H13B | 109.5 |
C6—C5—C4 | 121.5 (2) | H13A—C13—H13B | 109.5 |
C6—C5—H5 | 119.2 | N2—C13—H13C | 109.5 |
C4—C5—H5 | 119.2 | H13A—C13—H13C | 109.5 |
C7—C6—C5 | 119.4 (2) | H13B—C13—H13C | 109.5 |
C7—C6—H6 | 120.3 | O5—C14—H14A | 109.5 |
C5—C6—H6 | 120.3 | O5—C14—H14B | 109.5 |
O5—C7—C6 | 124.5 (2) | H14A—C14—H14B | 109.5 |
O5—C7—C8 | 115.3 (2) | O5—C14—H14C | 109.5 |
C6—C7—C8 | 120.1 (2) | H14A—C14—H14C | 109.5 |
C9—C8—C7 | 119.8 (2) | H14B—C14—H14C | 109.5 |
| | | |
C10—N1—C1—C2 | 5.6 (4) | C9—C4—C5—C6 | −1.7 (4) |
C11—N1—C1—C2 | −164.8 (3) | C1—C4—C5—C6 | 179.7 (2) |
C10—N1—C1—C4 | −173.1 (3) | C4—C5—C6—C7 | 0.4 (4) |
C11—N1—C1—C4 | 16.5 (4) | C14—O5—C7—C6 | 2.1 (4) |
N1—C1—C2—C3 | −171.2 (3) | C14—O5—C7—C8 | −178.4 (3) |
C4—C1—C2—C3 | 7.4 (4) | C5—C6—C7—O5 | −179.1 (2) |
C13—N2—C3—C2 | −177.4 (3) | C5—C6—C7—C8 | 1.4 (4) |
C12—N2—C3—C2 | −1.5 (5) | O5—C7—C8—C9 | 178.7 (2) |
C1—C2—C3—N2 | −177.9 (3) | C6—C7—C8—C9 | −1.8 (4) |
N1—C1—C4—C5 | −123.3 (3) | C7—C8—C9—C4 | 0.4 (4) |
C2—C1—C4—C5 | 58.0 (4) | C5—C4—C9—C8 | 1.3 (4) |
N1—C1—C4—C9 | 58.1 (3) | C1—C4—C9—C8 | 179.9 (2) |
C2—C1—C4—C9 | −120.5 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O5i | 0.93 | 2.59 | 3.325 (4) | 136 |
C10—H10C···O3ii | 0.96 | 2.59 | 3.379 (5) | 140 |
C11—H11A···O1iii | 0.96 | 2.55 | 3.251 (5) | 130 |
C11—H11B···O3ii | 0.96 | 2.59 | 3.393 (6) | 141 |
C12—H12C···O2iv | 0.96 | 2.59 | 3.506 (4) | 160 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2; (iv) −x+1, −y+1, −z+1. |