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organic compounds
(2E,4E)-2-Cyano-5-dipropylamino-N,N-dimethylpenta-2,4-dienamide
aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
*Correspondence e-mail: duxiaohua@zjut.edu.cn
In the title compound, C14H23N3O, the n-propyl group is disordered over two orientations with an occupancy ratio of 0.778 (3):0.222 (3). In the crystal, molecules are linked by pairs of weak C—H⋯O interactions into inversion dimers with an R22(14) graph-set motif.
Related literature
For applications of the title compound, see: Bryson et al. (1976). For the synthesis of N,N-dimethylcyanoacetamide, see: Basheer et al. (2007
). For hydrogen-bond graph-set motifs, see Etter et al. (1990
). For a description of the Cambridge Structural Database, see Allen (2002
). For structures with disordered n-propylgroups attached to CH2-N-CH2, see: Bouwman et al. (2000
); Liu et al. (2005
); Wang et al. (2009
). For the extinction correction, see: Becker & Coppens (1974
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: PROCESS-AUTO (Rigaku, 2006); cell PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007
); program(s) used to solve structure: SIR97 (Altomare et al., 1999)
; program(s) used to refine structure: JANA2006 (Petricek et al., 2006
); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997
); software used to prepare material for publication: WinGX (Farrugia, 1999
).
Supporting information
10.1107/S1600536812013797/fb2241sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812013797/fb2241Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812013797/fb2241Isup3.cml
To a three-necked flask, 3-dipropylaminopropenal (31 g, 0.2 mol), N,N-dimethylcyanoacetamide (22.6 g, 0.2 mol) (Basheer et al., 2007), anhydrous acetic acid (2.4 g, 0.04 mol), anhydrous monoethanolamine (2.44 g, 0.04 mol) and toluene (50 ml) were added. The mixture was stirred and heated to reflux for about 3 h and the generated water was separated by azeotropic distillation. After the reaction had completed, toluene was removed under vacuum. Then ethyl acetate (60 ml) was added to the residue and stirred at room temperature for 2 h. The precipitate was filtered to yield (2E,4E) -2-cyano-5-(dipropylamino)-N,N-dimethyl-2,4-pentadienamide (40 g, yield 80%). Single crystals were obtained as light yellow blocks (about 0.5–1 mm size) by slow evaporation at room temperature from a solution in petroleum ether (30–60°C).
The initial determination of the structural model yielded the non-disordered non-hydrogen atoms in the structure as well as the atoms C12a\C13a\C14a which form the dominant part of the disordered n-propyl chain. The difference
has shown other maxima corresponding to the atoms of the less occupied disordered chain C12b\C13b\C14b. Moreover, the difference has also shown the hydrogen positions of all the hydrogens with exception of those pertinent to the less occupied n-propyl chain. The non-hydrogen atoms of both disoredered chains were related approximately by reflection through a non crystallographic mirror plane. The non-proper symmetry that related the disordered chains has been respected in the which assumed that both chains were identical except for the inversion between them. Thus, the individual parameters of the atoms in the chain were refined in addition to the positional parameters of each of the disordered chain. Moreover, the occupational parameters of both chains were constrained to equal to 1.0. The described procedure infers that the positions of the methyl hydrogens of C14b which are not observable in the difference electron density maps can be biased because the methyl hydrogens pertinent to C14a and C14b need not be related by the reflection through the non-crystallographic mirror plane. The riding-atom approximation has been used for all the H-atoms in the structure: The used constraints are Csp2-Hsp2=0.93, CmethylHmethyl=0.96, Cmethylene-Hmethylene=0.97 Å. UisoHsp2=1.2UeqCsp2, UisoHmethylene=1.2UeqCmethylene, UisoHmethyl=1.5UeqCmethyl.Data collection: PROCESS-AUTO (Rigaku, 2006); cell
PROCESS-AUTO (Rigaku, 2006); data reduction: CrystalStructure (Rigaku, 2007); program(s) used to solve structure: SIR97 (Altomare et al. , 1999); program(s) used to refine structure: JANA2006 (Petricek et al., 2006); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).C14H23N3O | F(000) = 544 |
Mr = 249.35 | Dx = 1.090 Mg m−3 |
Monoclinic, P21/c | Melting point = 343–345 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0177 (6) Å | Cell parameters from 7731 reflections |
b = 14.0654 (9) Å | θ = 3.4–27.4° |
c = 12.9008 (8) Å | µ = 0.07 mm−1 |
β = 111.768 (2)° | T = 296 K |
V = 1519.63 (17) Å3 | Block, yellow |
Z = 4 | 0.48 × 0.46 × 0.28 mm |
Rigaku R-AXIS RAPID/ZJUG diffractometer | 3321 independent reflections |
Radiation source: rotating anode | 1412 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.056 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.0°, θmin = 3.4° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −17→17 |
Tmin = 0.957, Tmax = 0.981 | l = −16→16 |
14122 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.115 | Weighting scheme based on measured s.u.'s w = 1/(σ2(I) + 0.0004I2) |
S = 1.49 | (Δ/σ)max = 0.008 |
3321 reflections | Δρmax = 0.17 e Å−3 |
171 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: B–C type 1 Lorentzian isotropic (Becker & Coppens, 1974) |
93 constraints | Extinction coefficient: 21000 (2000) |
Primary atom site location: structure-invariant direct methods |
C14H23N3O | V = 1519.63 (17) Å3 |
Mr = 249.35 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.0177 (6) Å | µ = 0.07 mm−1 |
b = 14.0654 (9) Å | T = 296 K |
c = 12.9008 (8) Å | 0.48 × 0.46 × 0.28 mm |
β = 111.768 (2)° |
Rigaku R-AXIS RAPID/ZJUG diffractometer | 3321 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1412 reflections with I > 3σ(I) |
Tmin = 0.957, Tmax = 0.981 | Rint = 0.056 |
14122 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.115 | H-atom parameters constrained |
S = 1.49 | Δρmax = 0.17 e Å−3 |
3321 reflections | Δρmin = −0.14 e Å−3 |
171 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.7710 (2) | 0.36154 (14) | 0.45084 (13) | 0.0577 (8) | |
C3 | 0.5630 (2) | 0.33029 (13) | 0.52819 (12) | 0.0575 (7) | |
H1c3 | 0.53292 | 0.393093 | 0.509106 | 0.0689* | |
C4 | 0.4773 (2) | 0.28096 (14) | 0.58200 (13) | 0.0609 (8) | |
H1c4 | 0.499509 | 0.217163 | 0.600079 | 0.073* | |
N1 | 0.86144 (17) | 0.32384 (10) | 0.39765 (11) | 0.0596 (6) | |
O1 | 0.76404 (15) | 0.44850 (10) | 0.46179 (10) | 0.0806 (7) | |
C8 | 0.7432 (2) | 0.20380 (15) | 0.53474 (14) | 0.0613 (8) | |
C2 | 0.6858 (2) | 0.29684 (13) | 0.50038 (13) | 0.0539 (7) | |
N2 | 0.27560 (19) | 0.29019 (11) | 0.66391 (12) | 0.0705 (8) | |
C5 | 0.3609 (2) | 0.32599 (13) | 0.60832 (13) | 0.0601 (8) | |
H5 | 0.339131 | 0.388673 | 0.584583 | 0.0721* | |
C7 | 0.8384 (2) | 0.22932 (13) | 0.34734 (14) | 0.0763 (10) | |
H1c7 | 0.920869 | 0.187559 | 0.393177 | 0.1145* | |
H2c7 | 0.736089 | 0.205042 | 0.341428 | 0.1145* | |
H3c7 | 0.843117 | 0.233226 | 0.27433 | 0.1145* | |
C6 | 0.9693 (2) | 0.38499 (14) | 0.36768 (16) | 0.0766 (10) | |
H1c6 | 0.915903 | 0.408578 | 0.293221 | 0.1149* | |
H2c6 | 1.061854 | 0.349311 | 0.371235 | 0.1149* | |
H3c6 | 1.001483 | 0.437455 | 0.418793 | 0.1149* | |
C9 | 0.1604 (2) | 0.34923 (13) | 0.68939 (16) | 0.0725 (9) | |
H1c9 | 0.060681 | 0.314778 | 0.671024 | 0.087* | |
H2c9 | 0.133945 | 0.404351 | 0.640731 | 0.087* | |
N3 | 0.7901 (2) | 0.12920 (14) | 0.56658 (14) | 0.0875 (9) | |
C10 | 0.2176 (3) | 0.38138 (15) | 0.80951 (16) | 0.0829 (10) | |
H1c10 | 0.136486 | 0.42087 | 0.820581 | 0.0995* | |
H2c10 | 0.229544 | 0.326592 | 0.857613 | 0.0995* | |
C11 | 0.3729 (3) | 0.43521 (19) | 0.84523 (18) | 0.1130 (13) | |
H1c11 | 0.401634 | 0.455953 | 0.921073 | 0.1694* | |
H2c11 | 0.360998 | 0.489496 | 0.797697 | 0.1694* | |
H3c11 | 0.455082 | 0.3945 | 0.839672 | 0.1694* | |
C12a | 0.3146 (3) | 0.19427 (17) | 0.7201 (2) | 0.0660 (11) | 0.778 (3) |
H1c12a | 0.289827 | 0.19388 | 0.787092 | 0.0792* | 0.778 (3) |
H2c12a | 0.427849 | 0.181788 | 0.741427 | 0.0792* | 0.778 (3) |
C13a | 0.2208 (6) | 0.1178 (3) | 0.6423 (4) | 0.1043 (16) | 0.778 (3) |
H1c13a | 0.108059 | 0.133368 | 0.615493 | 0.1252* | 0.778 (3) |
H2c13a | 0.256201 | 0.112372 | 0.580105 | 0.1252* | 0.778 (3) |
C14a | 0.2497 (11) | 0.0232 (3) | 0.7062 (8) | 0.168 (4) | 0.778 (3) |
H2c14a | 0.337182 | 0.030256 | 0.7764 | 0.2515* | 0.778 (3) |
H1c14a | 0.274799 | −0.02531 | 0.662984 | 0.2515* | 0.778 (3) |
H3c14a | 0.155293 | 0.005554 | 0.719274 | 0.2515* | 0.778 (3) |
C12b | 0.2241 (11) | 0.1875 (6) | 0.6423 (7) | 0.0660 (12) | 0.222 (3) |
H1c12b | 0.114942 | 0.178009 | 0.636844 | 0.0792* | 0.222 (3) |
H2c12b | 0.233741 | 0.162761 | 0.574845 | 0.0792* | 0.222 (3) |
C13b | 0.3354 (13) | 0.1344 (7) | 0.7415 (8) | 0.1043 (18) | 0.222 (3) |
H1c13b | 0.333099 | 0.16291 | 0.809346 | 0.1252* | 0.222 (3) |
H2c13b | 0.442702 | 0.136583 | 0.74116 | 0.1252* | 0.222 (3) |
C14b | 0.2797 (16) | 0.0305 (7) | 0.7341 (10) | 0.168 (4) | 0.222 (3) |
H2c14b | 0.200701 | 0.018635 | 0.661289 | 0.2515* | 0.222 (3) |
H1c14b | 0.369246 | −0.01099 | 0.746841 | 0.2515* | 0.222 (3) |
H3c14b | 0.234411 | 0.019052 | 0.789557 | 0.2515* | 0.222 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0571 (11) | 0.0605 (13) | 0.0590 (10) | −0.0015 (10) | 0.0255 (9) | −0.0007 (9) |
C3 | 0.0606 (11) | 0.0574 (12) | 0.0577 (10) | −0.0015 (9) | 0.0257 (9) | −0.0009 (8) |
C4 | 0.0639 (12) | 0.0587 (12) | 0.0708 (11) | −0.0003 (10) | 0.0376 (10) | 0.0002 (9) |
N1 | 0.0639 (10) | 0.0602 (10) | 0.0652 (9) | −0.0069 (8) | 0.0361 (8) | −0.0048 (7) |
O1 | 0.0962 (10) | 0.0573 (9) | 0.1103 (10) | −0.0023 (8) | 0.0641 (8) | 0.0002 (7) |
C8 | 0.0594 (12) | 0.0697 (14) | 0.0619 (11) | −0.0027 (10) | 0.0308 (9) | 0.0044 (10) |
C2 | 0.0555 (11) | 0.0552 (12) | 0.0561 (10) | −0.0014 (9) | 0.0265 (8) | 0.0013 (8) |
N2 | 0.0782 (11) | 0.0606 (11) | 0.0934 (11) | 0.0013 (9) | 0.0559 (9) | 0.0033 (8) |
C5 | 0.0620 (12) | 0.0619 (13) | 0.0623 (11) | −0.0037 (10) | 0.0299 (9) | 0.0011 (9) |
C7 | 0.0923 (16) | 0.0766 (15) | 0.0707 (13) | −0.0047 (12) | 0.0426 (12) | −0.0117 (10) |
C6 | 0.0767 (14) | 0.0827 (15) | 0.0868 (14) | −0.0099 (11) | 0.0494 (12) | 0.0022 (11) |
C9 | 0.0594 (12) | 0.0819 (15) | 0.0878 (13) | 0.0070 (10) | 0.0408 (10) | −0.0004 (10) |
N3 | 0.0948 (13) | 0.0784 (13) | 0.1020 (13) | 0.0141 (10) | 0.0513 (10) | 0.0235 (10) |
C10 | 0.0889 (16) | 0.0922 (16) | 0.0831 (14) | 0.0141 (13) | 0.0498 (11) | 0.0037 (11) |
C11 | 0.0842 (16) | 0.138 (2) | 0.1120 (19) | 0.0011 (16) | 0.0305 (14) | −0.0358 (17) |
C12a | 0.0678 (15) | 0.0697 (18) | 0.0709 (16) | −0.0006 (13) | 0.0378 (13) | 0.0027 (13) |
C13a | 0.095 (2) | 0.084 (2) | 0.143 (3) | −0.0158 (19) | 0.0541 (18) | −0.024 (2) |
C14a | 0.199 (5) | 0.0557 (19) | 0.302 (7) | −0.009 (3) | 0.156 (4) | −0.002 (3) |
C12b | 0.064 (2) | 0.0695 (18) | 0.0744 (14) | −0.0016 (14) | 0.0367 (13) | 0.0021 (12) |
C13b | 0.127 (3) | 0.100 (2) | 0.0975 (19) | 0.031 (2) | 0.0550 (18) | 0.0268 (17) |
C14b | 0.251 (9) | 0.078 (2) | 0.235 (4) | 0.054 (4) | 0.161 (4) | 0.064 (3) |
C1—N1 | 1.354 (3) | C9—C10 | 1.510 (3) |
C1—O1 | 1.236 (2) | C10—H1c10 | 0.97 |
C1—C2 | 1.480 (3) | C10—H2c10 | 0.97 |
C3—H1c3 | 0.93 | C10—C11 | 1.506 (3) |
C3—C4 | 1.399 (3) | C11—H1c11 | 0.96 |
C3—C2 | 1.368 (3) | C11—H2c11 | 0.96 |
C4—H1c4 | 0.93 | C11—H3c11 | 0.96 |
C4—C5 | 1.373 (3) | C12a—H1c12a | 0.97 |
N1—C7 | 1.460 (2) | C12a—H2c12a | 0.97 |
N1—C6 | 1.454 (3) | C12a—C13a | 1.500 (5) |
C8—C2 | 1.417 (3) | C13a—H1c13a | 0.97 |
C8—N3 | 1.149 (3) | C13a—H2c13a | 0.97 |
N2—C5 | 1.330 (3) | C13a—C14a | 1.536 (8) |
N2—C9 | 1.460 (3) | C14a—H2c14a | 0.96 |
N2—C12a | 1.510 (3) | C14a—H1c14a | 0.96 |
N2—C12b | 1.512 (9) | C14a—H3c14a | 0.96 |
C5—H5 | 0.93 | C12b—H1c12b | 0.97 |
C7—H1c7 | 0.96 | C12b—H2c12b | 0.97 |
C7—H2c7 | 0.96 | C12b—C13b | 1.500 (12) |
C7—H3c7 | 0.96 | C13b—H1c13b | 0.97 |
C6—H1c6 | 0.96 | C13b—H2c13b | 0.97 |
C6—H2c6 | 0.96 | C13b—C14b | 1.536 (14) |
C6—H3c6 | 0.96 | C14b—H2c14b | 0.96 |
C9—H1c9 | 0.97 | C14b—H1c14b | 0.96 |
C9—H2c9 | 0.97 | C14b—H3c14b | 0.96 |
N1—C1—O1 | 120.76 (19) | H1c10—C10—H2c10 | 105.7788 |
N1—C1—C2 | 119.01 (17) | H1c10—C10—C11 | 109.4707 |
O1—C1—C2 | 120.17 (18) | H2c10—C10—C11 | 109.4709 |
H1c3—C3—C4 | 116.2395 | C10—C11—H1c11 | 109.4713 |
H1c3—C3—C2 | 116.2397 | C10—C11—H2c11 | 109.4711 |
C4—C3—C2 | 127.52 (17) | C10—C11—H3c11 | 109.4707 |
C3—C4—H1c4 | 119.7468 | H1c11—C11—H2c11 | 109.4715 |
C3—C4—C5 | 120.51 (17) | H1c11—C11—H3c11 | 109.4716 |
H1c4—C4—C5 | 119.7456 | H2c11—C11—H3c11 | 109.4712 |
C1—N1—C7 | 124.68 (17) | N2—C12a—H1c12a | 110.0628 |
C1—N1—C6 | 119.43 (16) | N2—C12a—H2c12a | 109.3494 |
C7—N1—C6 | 114.79 (17) | N2—C12a—C13a | 110.3 (2) |
C2—C8—N3 | 177.4 (2) | H1c12a—C12a—H2c12a | 108.1807 |
C1—C2—C3 | 120.15 (16) | H1c12a—C12a—C13a | 109.4711 |
C1—C2—C8 | 121.00 (18) | H2c12a—C12a—C13a | 109.4714 |
C3—C2—C8 | 118.23 (18) | C12a—C13a—H1c13a | 109.4716 |
C5—N2—C9 | 120.55 (16) | C12a—C13a—H2c13a | 109.4709 |
C5—N2—C12a | 121.25 (19) | C12a—C13a—C14a | 108.7 (4) |
C5—N2—C12b | 117.5 (5) | H1c13a—C13a—H2c13a | 110.2327 |
C9—N2—C12a | 117.31 (19) | H1c13a—C13a—C14a | 109.4711 |
C9—N2—C12b | 112.9 (4) | H2c13a—C13a—C14a | 109.4713 |
C4—C5—N2 | 127.39 (17) | C13a—C14a—H2c14a | 109.4714 |
C4—C5—H5 | 116.3055 | C13a—C14a—H1c14a | 109.4717 |
N2—C5—H5 | 116.3064 | C13a—C14a—H3c14a | 109.4712 |
N1—C7—H1c7 | 109.4707 | H2c14a—C14a—H1c14a | 109.4709 |
N1—C7—H2c7 | 109.4708 | H2c14a—C14a—H3c14a | 109.4711 |
N1—C7—H3c7 | 109.4714 | N2—C12b—H1c12b | 112.2217 |
H1c7—C7—H2c7 | 109.471 | N2—C12b—H2c12b | 112.6045 |
H1c7—C7—H3c7 | 109.4722 | N2—C12b—C13b | 104.8 (6) |
H2c7—C7—H3c7 | 109.4713 | H1c12b—C12b—H2c12b | 108.1808 |
N1—C6—H1c6 | 109.4714 | H1c12b—C12b—C13b | 109.4711 |
N1—C6—H2c6 | 109.4711 | H2c12b—C12b—C13b | 109.4714 |
N1—C6—H3c6 | 109.472 | C12b—C13b—H1c13b | 109.4716 |
H1c6—C6—H2c6 | 109.4709 | C12b—C13b—H2c13b | 109.471 |
H1c6—C6—H3c6 | 109.4706 | C12b—C13b—C14b | 108.7 (8) |
H2c6—C6—H3c6 | 109.4713 | H1c13b—C13b—H2c13b | 110.2327 |
N2—C9—H1c9 | 109.4719 | H1c13b—C13b—C14b | 109.4711 |
N2—C9—H2c9 | 109.4712 | H2c13b—C13b—C14b | 109.4713 |
N2—C9—C10 | 113.62 (15) | C13b—C14b—H2c14b | 109.4714 |
H1c9—C9—H2c9 | 104.974 | C13b—C14b—H1c14b | 109.4718 |
H1c9—C9—C10 | 109.471 | C13b—C14b—H3c14b | 109.4712 |
H2c9—C9—C10 | 109.4713 | H2c14b—C14b—H1c14b | 109.4709 |
C9—C10—H1c10 | 109.4712 | H2c14b—C14b—H3c14b | 109.4711 |
C9—C10—H2c10 | 109.4722 | H1c14b—C14b—H3c14b | 109.4709 |
C9—C10—C11 | 112.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.93 | 2.46 | 3.375 (2) | 168 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H23N3O |
Mr | 249.35 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 9.0177 (6), 14.0654 (9), 12.9008 (8) |
β (°) | 111.768 (2) |
V (Å3) | 1519.63 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.48 × 0.46 × 0.28 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID/ZJUG diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.957, 0.981 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 14122, 3321, 1412 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.115, 1.49 |
No. of reflections | 3321 |
No. of parameters | 171 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.14 |
Computer programs: PROCESS-AUTO (Rigaku, 2006), CrystalStructure (Rigaku, 2007), SIR97 (Altomare et al. , 1999), JANA2006 (Petricek et al., 2006), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.93 | 2.46 | 3.375 (2) | 168 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
The authors thank Professor Jian-Ming Gu of Zhejiang University for the structure analysis.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The title compound is a useful intermediate for the synthesis of 2-chloro-N,N-dimethylnicotinamide derivatives, which are widely used in syntheses of pharmaceutics and pesticides (Bryson et al., 1976). In order to establish conformational details of the title molecule, its crystal structure has been determined. In the crystal structure, the n-propyl composed of C12\C13\C14 is disordered over two positions with different occupancies that are 0.778 (3) and 0.222 (3) for the chains A and B, respectively. Both disordered chains are related approximately by a non-crystallographic symmetry plane. As shown in Fig. 1, O1 is deviated by 3.6 (4) Å from the plane composed of C1\C2\C3\C4\C5.
A search in the Cambridge Structural Database (Allen, 2002) for the structures that contain a fragment of the n-propyl attached to CH2-N-CH2 where N is not involved in a ring yielded 14 hits from which three of them contained a disordered n-propyl fragment. These three structures are FEDKEF, i. e. N,N-bis (anthracen-9-ylmethyl)propylamine determined by Liu et al. (2005); HUYWAA, i. e. (µ2-N,N-bis((diphenylphosphino)methyl) -n-propylamine-P,P') -bis(µ2-propane-1,3-dithiolato-S,S,S',S')-decacarbonyl-tetra-iron dichloromethane solvate determined by Wang et al. (2009); WIGKOM, i. e. N,N-bis(2-ethyl-5-methyl-imidazol -4-ylmethyl)aminopropane monohydrate determined by Bouwman et al. (2000). These examples show that the disorder of n-propyl chain is rather common in molecules containing such a motif as it happens to be present in the title structure (Fig. 1).
There are present only weak intermolecular interactions in the structure among which C5—H5···O1i is most prominent (the symmetry code i: 1-x, 1-y, 1-z). As shown in Fig. 2, a centrosymmetric dimer about the crystallographic inversion centre is formed by a pair of these hydrogen bonds with the graph set motif R22(14) (Etter et al., 1990).