1-Phenyl-3-[(1-phenyl­ethyl)amino]but-2-en-1-one

Shi, Y.-C.; Sui, C.-X.; Yang, H.-M.

doi:10.1107/S1600536805031648

1-Phenyl-3-[(1-phenylethyl)amino]but-2-en-1-one

The title compound, C₁₈H₁₉NO, has been synthesized by the condensation reaction of benzoylacetone and L-(−)-α-phenylethylamine. The enaminone structure is stabilized by a strong N—H

O=C intramolecular hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031648/hg6254sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031648/hg6254Isup2.hkl Contains datablock I

CCDC reference: 289768

checkCIF report

Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.010 Å
R factor = 0.057
wR factor = 0.212
Data-to-parameter ratio = 9.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         46 Perc.
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C1     -C6            1.37 Ang.
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C13    -C18           1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10

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           25.96
           From the CIF: _reflns_number_total               1767
           Count of symmetry unique reflns         1767
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

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

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

1-Phenyl-3-[(1-phenylethyl)amino]but-2-en-1-one top

Crystal data top

C₁₈H₁₉NO	D_x = 1.124 Mg m⁻³
M_r = 265.34	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 25 reflections
a = 10.257 (2) Å	θ = 10–13°
b = 11.856 (2) Å	µ = 0.07 mm⁻¹
c = 12.892 (3) Å	T = 297 K
V = 1567.8 (5) Å³	Prism, colourless
Z = 4	0.20 × 0.20 × 0.10 mm
F(000) = 568

Data collection top

Enraf–Nonius CAD-4 diffractometer	810 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 26.0°, θ_min = 2.3°
ω/2θ scans	h = 0→12
Absorption correction: empirical (using intensity measurements) via ψ scan (North et al., 1968)	k = 0→14
T_min = 0.974, T_max = 0.987	l = 0→15
1767 measured reflections	3 standard reflections every 200 reflections
1767 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.057	H-atom parameters constrained
wR(F²) = 0.212	w = 1/[σ²(F_o²) + (0.0927P)² + 0.2856P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
1767 reflections	Δρ_max = 0.13 e Å⁻³
184 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.120 (13)

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	U_iso*/U_eq
O	0.6236 (4)	0.8151 (3)	0.3808 (3)	0.0889 (12)
N	0.7826 (5)	0.6498 (4)	0.4405 (4)	0.0903 (15)
H1N	0.7088	0.6833	0.4473	0.108*
C6	0.6753 (5)	0.9242 (4)	0.2331 (4)	0.0699 (14)
C8	0.8193 (6)	0.7704 (5)	0.2986 (5)	0.0894 (17)
H8	0.8744	0.7886	0.2437	0.107*
C7	0.7039 (6)	0.8332 (4)	0.3092 (4)	0.0753 (15)
C13	0.8092 (7)	0.4441 (5)	0.4694 (4)	0.0881 (18)
C1	0.5841 (6)	1.0040 (5)	0.2593 (5)	0.0949 (18)
H1	0.5412	0.9978	0.3226	0.114*
C12	0.8114 (7)	0.5605 (5)	0.5166 (5)	0.0965 (19)
H12	0.8994	0.5739	0.5434	0.116*
C3	0.6130 (8)	1.1011 (6)	0.1012 (7)	0.109 (2)
H3	0.5920	1.1602	0.0568	0.131*
C2	0.5543 (8)	1.0920 (6)	0.1956 (7)	0.111 (2)
H2	0.4940	1.1459	0.2167	0.133*
C9	0.8568 (6)	0.6844 (6)	0.3630 (6)	0.0965 (19)
C14	0.9075 (8)	0.3661 (6)	0.4868 (6)	0.119 (2)
H14	0.9797	0.3864	0.5262	0.143*
C17	0.6978 (8)	0.3048 (7)	0.3703 (6)	0.117 (2)
H17	0.6253	0.2838	0.3314	0.141*
C4	0.7022 (8)	1.0231 (8)	0.0729 (6)	0.122 (3)
H4	0.7435	1.0293	0.0089	0.147*
C18	0.7052 (8)	0.4107 (5)	0.4100 (5)	0.101 (2)
H18	0.6384	0.4617	0.3966	0.122*
C16	0.7950 (9)	0.2291 (6)	0.3867 (6)	0.119 (2)
H16	0.7905	0.1576	0.3574	0.143*
C15	0.8990 (9)	0.2587 (7)	0.4463 (7)	0.132 (3)
H15	0.9645	0.2065	0.4598	0.158*
C5	0.7329 (7)	0.9342 (6)	0.1377 (5)	0.099 (2)
H5	0.7933	0.8805	0.1164	0.119*
C11	0.7168 (10)	0.5734 (6)	0.6062 (5)	0.141 (3)
H11A	0.7260	0.6472	0.6360	0.212*
H11B	0.7354	0.5174	0.6580	0.212*
H11C	0.6293	0.5637	0.5815	0.212*
C10	0.9880 (7)	0.6279 (6)	0.3487 (7)	0.141 (3)
H10A	1.0309	0.6593	0.2891	0.211*
H10B	0.9756	0.5484	0.3387	0.211*
H10C	1.0406	0.6402	0.4092	0.211*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.093 (3)	0.082 (2)	0.092 (3)	−0.004 (2)	0.003 (2)	0.007 (2)
N	0.097 (4)	0.080 (3)	0.095 (3)	0.005 (3)	−0.017 (3)	0.010 (3)
C6	0.068 (3)	0.062 (3)	0.079 (4)	−0.013 (3)	−0.015 (3)	−0.002 (3)
C8	0.077 (4)	0.089 (4)	0.102 (4)	−0.005 (4)	0.000 (4)	0.019 (4)
C7	0.072 (4)	0.069 (3)	0.084 (4)	−0.010 (3)	−0.011 (3)	0.000 (3)
C13	0.104 (5)	0.082 (4)	0.078 (4)	−0.011 (4)	−0.016 (4)	0.007 (3)
C1	0.108 (4)	0.081 (4)	0.095 (4)	0.000 (4)	−0.011 (4)	0.008 (4)
C12	0.118 (5)	0.081 (4)	0.091 (4)	−0.001 (4)	−0.029 (4)	0.000 (4)
C3	0.113 (6)	0.082 (4)	0.133 (7)	−0.026 (4)	−0.040 (5)	0.038 (5)
C2	0.123 (6)	0.084 (5)	0.127 (6)	0.013 (4)	−0.027 (5)	0.001 (5)
C9	0.088 (5)	0.091 (4)	0.110 (5)	−0.003 (4)	−0.004 (4)	0.013 (4)
C14	0.128 (6)	0.102 (5)	0.128 (5)	0.009 (5)	−0.034 (5)	0.008 (5)
C17	0.111 (6)	0.108 (5)	0.134 (6)	−0.023 (6)	−0.008 (5)	−0.010 (5)
C4	0.106 (6)	0.147 (6)	0.115 (6)	−0.012 (6)	0.001 (5)	0.048 (6)
C18	0.116 (5)	0.083 (4)	0.104 (4)	−0.008 (4)	−0.008 (5)	0.005 (4)
C16	0.130 (6)	0.091 (5)	0.137 (6)	−0.011 (6)	0.015 (6)	−0.012 (5)
C15	0.127 (7)	0.094 (5)	0.174 (8)	0.012 (5)	−0.020 (7)	0.012 (6)
C5	0.091 (4)	0.110 (5)	0.096 (4)	0.001 (4)	0.008 (4)	0.012 (4)
C11	0.230 (10)	0.117 (6)	0.077 (4)	0.022 (7)	−0.007 (6)	0.000 (4)
C10	0.097 (5)	0.143 (7)	0.182 (7)	0.029 (5)	0.008 (5)	0.051 (7)

Geometric parameters (Å, º) top

O—C7	1.256 (6)	C3—H3	0.9300
N—C9	1.321 (7)	C2—H2	0.9300
N—C12	1.473 (7)	C14—C15	1.379 (9)
N—H1N	0.8600	C14—H14	0.9300
C6—C5	1.369 (7)	C17—C16	1.358 (10)
C6—C1	1.373 (7)	C17—C18	1.359 (9)
C6—C7	1.487 (7)	C17—H17	0.9300
C7—C8	1.405 (8)	C4—C5	1.382 (9)
C8—C9	1.370 (8)	C4—H4	0.9300
C8—H8	0.9300	C18—H18	0.9300
C9—C10	1.514 (9)	C16—C15	1.361 (10)
C13—C18	1.371 (9)	C16—H16	0.9300
C13—C14	1.386 (9)	C15—H15	0.9300
C11—C12	1.516 (10)	C5—H5	0.9300
C12—C13	1.509 (8)	C11—H11A	0.9600
C1—C2	1.361 (8)	C11—H11B	0.9600
C1—H1	0.9300	C11—H11C	0.9600
C12—H12	0.9800	C10—H10A	0.9600
C3—C4	1.351 (10)	C10—H10B	0.9600
C3—C2	1.363 (10)	C10—H10C	0.9600

C9—N—H1N	116.2	C15—C14—C13	120.6 (7)
C12—N—H1N	116.2	C15—C14—H14	119.7
C5—C6—C1	117.1 (5)	C13—C14—H14	119.7
C5—C6—C7	124.7 (6)	C16—C17—C18	120.7 (8)
C1—C6—C7	118.2 (5)	C16—C17—H17	119.6
C9—C8—H8	117.6	C18—C17—H17	119.6
C7—C8—H8	117.6	C3—C4—C5	120.9 (7)
O—C7—C6	118.6 (5)	C3—C4—H4	119.6
O—C7—C8	122.3 (5)	C5—C4—H4	119.6
C6—C7—C8	119.1 (5)	C17—C18—C13	121.4 (7)
C9—N—C12	127.7 (6)	C17—C18—H18	119.3
C7—C8—C9	124.9 (6)	C13—C18—H18	119.3
N—C9—C8	121.8 (6)	C17—C16—C15	119.6 (7)
N—C9—C10	117.8 (6)	C17—C16—H16	120.2
C8—C9—C10	120.3 (7)	C15—C16—H16	120.2
C18—C13—C14	117.6 (6)	C16—C15—C14	120.1 (8)
C18—C13—C12	120.0 (7)	C16—C15—H15	120.0
C14—C13—C12	122.3 (6)	C14—C15—H15	120.0
C2—C1—C6	122.2 (7)	C6—C5—C4	120.7 (6)
C2—C1—H1	118.9	C6—C5—H5	119.6
C6—C1—H1	118.9	C4—C5—H5	119.6
N—C12—C11	107.9 (6)	C12—C11—H11A	109.5
N—C12—C13	112.7 (5)	C12—C11—H11B	109.5
C11—C12—C13	113.0 (6)	H11A—C11—H11B	109.5
N—C12—H12	107.7	C12—C11—H11C	109.5
C13—C12—H12	107.7	H11A—C11—H11C	109.5
C11—C12—H12	107.7	H11B—C11—H11C	109.5
C4—C3—C2	119.1 (7)	C9—C10—H10A	109.5
C4—C3—H3	120.5	C9—C10—H10B	109.5
C2—C3—H3	120.5	H10A—C10—H10B	109.5
C1—C2—C3	120.0 (7)	C9—C10—H10C	109.5
C1—C2—H2	120.0	H10A—C10—H10C	109.5
C3—C2—H2	120.0	H10B—C10—H10C	109.5

C9—C8—C7—O	0.2 (9)	C12—N—C9—C8	−178.7 (6)
C9—C8—C7—C6	−179.8 (6)	C12—N—C9—C10	−0.3 (10)
C5—C6—C7—O	−161.8 (5)	C7—C8—C9—N	2.6 (10)
C1—C6—C7—O	17.8 (7)	C7—C8—C9—C10	−175.7 (6)
C5—C6—C7—C8	18.2 (7)	C18—C13—C14—C15	−0.7 (10)
C1—C6—C7—C8	−162.2 (5)	C12—C13—C14—C15	176.9 (7)
C5—C6—C1—C2	−2.2 (8)	C2—C3—C4—C5	0.8 (11)
C7—C6—C1—C2	178.2 (5)	C16—C17—C18—C13	−1.3 (11)
C9—N—C12—C13	−70.1 (9)	C14—C13—C18—C17	0.6 (10)
C9—N—C12—C11	164.5 (6)	C12—C13—C18—C17	−177.0 (6)
C18—C13—C12—N	−50.0 (9)	C18—C17—C16—C15	2.1 (12)
C14—C13—C12—N	132.5 (6)	C17—C16—C15—C14	−2.2 (12)
C18—C13—C12—C11	72.6 (7)	C13—C14—C15—C16	1.5 (12)
C14—C13—C12—C11	−104.9 (8)	C1—C6—C5—C4	1.8 (8)
C6—C1—C2—C3	1.9 (10)	C7—C6—C5—C4	−178.6 (6)
C4—C3—C2—C1	−1.2 (10)	C3—C4—C5—C6	−1.2 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H1N···O	0.86	1.99	2.663 (6)	135
C1—H1···O	0.93	2.44	2.763 (7)	100

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1-Phenyl-3-[(1-phenyl­ethyl)amino]but-2-en-1-one

Supporting information

Key indicators

checkCIF/PLATON results

1-Phenyl-3-[(1-phenylethyl)amino]but-2-en-1-one