1-(4-{[(E)-(4-Diethyl­amino-2-hydroxyphenyl)methyl­ene]amino}phenyl)ethanone

The title compound, C₁₉H₂₂N₂O₂, is a Schiff base. Its mol­ecular conformation is stabilized by an O—H...N hydrogen bond. The crystal packing is characterized by C—H...π and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.040
• wR factor = 0.109
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

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Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: PLATON and SHELXL97.

1-(4-{[(E)-(4-Diethylamino-2-hydroxyphenyl)methylene]amino}phenyl)ethanone

Crystal data

C19H22N2O2	F(000) = 664
Mr = 310.39	Dx = 1.245 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12807 reflections
a = 16.0234 (16) Å	θ = 3.7–25.6°
b = 7.6225 (5) Å	µ = 0.08 mm^−1
c = 15.0652 (16) Å	T = 173 K
β = 115.828 (7)°	Block, orange brown
V = 1656.2 (3) Å^3	0.42 × 0.28 × 0.19 mm
Z = 4

Data collection

Stoe IPDS II two-circle diffractometer	2654 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite monochromator	θmax = 25.6°, θmin = 3.6°
ω scans	h = −19→18
13407 measured reflections	k = −9→9
3092 independent reflections	l = −18→18

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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.109	w = 1/[σ^2(Fo^2) + (0.0601P)^2 + 0.3519P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
3092 reflections	Δρmax = 0.21 e Å^−3
214 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (2)

Special details

Experimental. ;

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	0.48237 (7)	0.31316 (14)	0.38150 (7)	0.0248 (2)
C1	0.47354 (8)	0.38747 (16)	0.30007 (9)	0.0250 (3)
H1	0.5218	0.4612	0.3012	0.030*
C11	0.56015 (8)	0.34157 (16)	0.47302 (9)	0.0231 (3)
C12	0.56426 (9)	0.23931 (17)	0.55197 (9)	0.0277 (3)
H12	0.5157	0.1587	0.5418	0.033*
C13	0.63813 (9)	0.25367 (17)	0.64498 (9)	0.0287 (3)
H13	0.6398	0.1825	0.6975	0.034*
C14	0.71020 (8)	0.37251 (16)	0.66172 (9)	0.0247 (3)
C15	0.70476 (9)	0.47758 (18)	0.58314 (9)	0.0296 (3)
H15	0.7525	0.5604	0.5938	0.036*
C16	0.63127 (9)	0.46361 (18)	0.49013 (9)	0.0294 (3)
H16	0.6290	0.5365	0.4380	0.035*
C17	0.79289 (8)	0.38894 (17)	0.75984 (9)	0.0286 (3)
O17	0.85710 (6)	0.48683 (14)	0.77052 (7)	0.0381 (3)
C18	0.79640 (10)	0.2787 (2)	0.84472 (10)	0.0380 (3)
H18A	0.8526	0.3070	0.9044	0.057*
H18B	0.7971	0.1541	0.8289	0.057*
H18C	0.7417	0.3033	0.8560	0.057*
C21	0.39258 (8)	0.36067 (16)	0.20848 (9)	0.0233 (3)
C22	0.31639 (8)	0.25651 (15)	0.20272 (8)	0.0230 (3)
C23	0.23645 (8)	0.24237 (16)	0.11521 (9)	0.0240 (3)
H23	0.1868	0.1718	0.1133	0.029*
C24	0.22694 (8)	0.33073 (15)	0.02853 (8)	0.0224 (3)
C25	0.30439 (8)	0.43048 (17)	0.03326 (9)	0.0255 (3)
H25	0.3015	0.4875	−0.0241	0.031*
C26	0.38305 (8)	0.44394 (17)	0.12075 (9)	0.0255 (3)
H26	0.4333	0.5123	0.1223	0.031*
O22	0.32042 (6)	0.16937 (12)	0.28296 (6)	0.0314 (2)
H22	0.3796 (14)	0.200 (3)	0.3357 (14)	0.064 (6)*
N24	0.14626 (7)	0.32124 (14)	−0.05657 (7)	0.0258 (3)
C27	0.06225 (8)	0.23871 (18)	−0.05949 (9)	0.0285 (3)
H27A	0.0071	0.2981	−0.1101	0.034*
H27B	0.0611	0.2549	0.0052	0.034*
C28	0.05698 (10)	0.04354 (19)	−0.08295 (10)	0.0356 (3)
H28A	0.0000	−0.0055	−0.0840	0.053*
H28B	0.1109	−0.0163	−0.0324	0.053*
H28C	0.0567	0.0268	−0.1476	0.053*
C29	0.13424 (9)	0.41195 (18)	−0.14768 (9)	0.0298 (3)
H29A	0.0882	0.3477	−0.2053	0.036*
H29B	0.1939	0.4114	−0.1526	0.036*
C30	0.10206 (10)	0.60023 (19)	−0.15030 (11)	0.0392 (4)
H30A	0.0949	0.6561	−0.2118	0.059*
H30B	0.1481	0.6649	−0.0940	0.059*
H30C	0.0424	0.6012	−0.1468	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0236 (5)	0.0258 (5)	0.0238 (5)	0.0007 (4)	0.0092 (4)	−0.0012 (4)
C1	0.0236 (6)	0.0243 (6)	0.0288 (6)	−0.0008 (5)	0.0130 (5)	−0.0016 (5)
C11	0.0226 (6)	0.0226 (6)	0.0247 (6)	0.0033 (5)	0.0110 (5)	−0.0009 (5)
C12	0.0298 (6)	0.0269 (6)	0.0289 (6)	−0.0049 (5)	0.0150 (5)	−0.0018 (5)
C13	0.0352 (7)	0.0278 (7)	0.0253 (6)	0.0009 (5)	0.0154 (5)	0.0028 (5)
C14	0.0241 (6)	0.0255 (6)	0.0248 (6)	0.0052 (5)	0.0111 (5)	−0.0004 (5)
C15	0.0245 (6)	0.0316 (7)	0.0301 (7)	−0.0037 (5)	0.0094 (5)	0.0021 (5)
C16	0.0289 (6)	0.0317 (7)	0.0254 (6)	−0.0033 (5)	0.0099 (5)	0.0060 (5)
C17	0.0268 (6)	0.0326 (7)	0.0263 (6)	0.0090 (5)	0.0115 (5)	−0.0014 (5)
O17	0.0270 (5)	0.0497 (6)	0.0319 (5)	−0.0018 (4)	0.0076 (4)	−0.0022 (4)
C18	0.0363 (7)	0.0476 (9)	0.0262 (6)	0.0082 (6)	0.0099 (6)	0.0052 (6)
C21	0.0234 (6)	0.0224 (6)	0.0249 (6)	0.0013 (5)	0.0113 (5)	−0.0009 (5)
C22	0.0270 (6)	0.0204 (6)	0.0241 (6)	0.0018 (5)	0.0135 (5)	0.0013 (5)
C23	0.0235 (6)	0.0224 (6)	0.0277 (6)	−0.0028 (5)	0.0126 (5)	−0.0005 (5)
C24	0.0240 (6)	0.0211 (6)	0.0231 (6)	0.0028 (5)	0.0111 (5)	−0.0016 (5)
C25	0.0281 (6)	0.0270 (6)	0.0239 (6)	0.0000 (5)	0.0138 (5)	0.0021 (5)
C26	0.0247 (6)	0.0255 (6)	0.0293 (6)	−0.0028 (5)	0.0147 (5)	−0.0013 (5)
O22	0.0319 (5)	0.0351 (5)	0.0244 (5)	−0.0068 (4)	0.0097 (4)	0.0065 (4)
N24	0.0233 (5)	0.0283 (6)	0.0241 (5)	−0.0016 (4)	0.0088 (4)	0.0031 (4)
C27	0.0214 (6)	0.0344 (7)	0.0274 (6)	−0.0014 (5)	0.0085 (5)	0.0033 (5)
C28	0.0375 (7)	0.0358 (8)	0.0319 (7)	−0.0087 (6)	0.0136 (6)	0.0003 (6)
C29	0.0286 (6)	0.0371 (7)	0.0211 (6)	−0.0035 (5)	0.0085 (5)	0.0020 (5)
C30	0.0360 (7)	0.0351 (8)	0.0393 (8)	−0.0015 (6)	0.0096 (6)	0.0123 (6)

Geometric parameters (Å, º)

N1—C1	1.3018 (16)	C22—C23	1.3852 (16)
N1—C11	1.4156 (15)	C23—C24	1.4173 (17)
C1—C21	1.4383 (16)	C23—H23	0.9500
C1—H1	0.9500	C24—N24	1.3697 (15)
C11—C12	1.3995 (17)	C24—C25	1.4305 (17)
C11—C16	1.4052 (17)	C25—C26	1.3743 (17)
C12—C13	1.3897 (17)	C25—H25	0.9500
C12—H12	0.9500	C26—H26	0.9500
C13—C14	1.4015 (18)	O22—H22	0.96 (2)
C13—H13	0.9500	N24—C27	1.4691 (15)
C14—C15	1.4002 (18)	N24—C29	1.4726 (15)
C14—C17	1.4999 (17)	C27—C28	1.523 (2)
C15—C16	1.3870 (18)	C27—H27A	0.9900
C15—H15	0.9500	C27—H27B	0.9900
C16—H16	0.9500	C28—H28A	0.9800
C17—O17	1.2235 (17)	C28—H28B	0.9800
C17—C18	1.5108 (19)	C28—H28C	0.9800
C18—H18A	0.9800	C29—C30	1.520 (2)
C18—H18B	0.9800	C29—H29A	0.9900
C18—H18C	0.9800	C29—H29B	0.9900
C21—C26	1.4133 (17)	C30—H30A	0.9800
C21—C22	1.4268 (17)	C30—H30B	0.9800
C22—O22	1.3561 (14)	C30—H30C	0.9800
C1—N1—C11	122.64 (10)	C24—C23—H23	119.2
N1—C1—C21	121.63 (11)	N24—C24—C23	121.07 (11)
N1—C1—H1	119.2	N24—C24—C25	121.28 (11)
C21—C1—H1	119.2	C23—C24—C25	117.65 (10)
C12—C11—C16	118.60 (11)	C26—C25—C24	120.04 (11)
C12—C11—N1	115.98 (11)	C26—C25—H25	120.0
C16—C11—N1	125.41 (11)	C24—C25—H25	120.0
C13—C12—C11	121.14 (11)	C25—C26—C21	122.94 (11)
C13—C12—H12	119.4	C25—C26—H26	118.5
C11—C12—H12	119.4	C21—C26—H26	118.5
C12—C13—C14	120.36 (12)	C22—O22—H22	105.3 (12)
C12—C13—H13	119.8	C24—N24—C27	121.97 (10)
C14—C13—H13	119.8	C24—N24—C29	122.31 (10)
C15—C14—C13	118.34 (11)	C27—N24—C29	115.28 (9)
C15—C14—C17	119.23 (11)	N24—C27—C28	112.50 (11)
C13—C14—C17	122.42 (11)	N24—C27—H27A	109.1
C16—C15—C14	121.54 (12)	C28—C27—H27A	109.1
C16—C15—H15	119.2	N24—C27—H27B	109.1
C14—C15—H15	119.2	C28—C27—H27B	109.1
C15—C16—C11	119.99 (12)	H27A—C27—H27B	107.8
C15—C16—H16	120.0	C27—C28—H28A	109.5
C11—C16—H16	120.0	C27—C28—H28B	109.5
O17—C17—C14	120.78 (12)	H28A—C28—H28B	109.5
O17—C17—C18	120.60 (11)	C27—C28—H28C	109.5
C14—C17—C18	118.61 (12)	H28A—C28—H28C	109.5
C17—C18—H18A	109.5	H28B—C28—H28C	109.5
C17—C18—H18B	109.5	N24—C29—C30	111.88 (11)
H18A—C18—H18B	109.5	N24—C29—H29A	109.2
C17—C18—H18C	109.5	C30—C29—H29A	109.2
H18A—C18—H18C	109.5	N24—C29—H29B	109.2
H18B—C18—H18C	109.5	C30—C29—H29B	109.2
C26—C21—C22	116.87 (11)	H29A—C29—H29B	107.9
C26—C21—C1	121.21 (11)	C29—C30—H30A	109.5
C22—C21—C1	121.85 (11)	C29—C30—H30B	109.5
O22—C22—C23	118.39 (11)	H30A—C30—H30B	109.5
O22—C22—C21	120.74 (10)	C29—C30—H30C	109.5
C23—C22—C21	120.88 (11)	H30A—C30—H30C	109.5
C22—C23—C24	121.57 (11)	H30B—C30—H30C	109.5
C22—C23—H23	119.2
C11—N1—C1—C21	−178.13 (11)	C1—C21—C22—O22	−4.32 (18)
C1—N1—C11—C12	−173.84 (11)	C26—C21—C22—C23	−1.47 (17)
C1—N1—C11—C16	6.92 (19)	C1—C21—C22—C23	175.46 (11)
C16—C11—C12—C13	−1.77 (19)	O22—C22—C23—C24	179.52 (11)
N1—C11—C12—C13	178.94 (11)	C21—C22—C23—C24	−0.27 (18)
C11—C12—C13—C14	0.4 (2)	C22—C23—C24—N24	−177.47 (11)
C12—C13—C14—C15	1.14 (19)	C22—C23—C24—C25	2.31 (17)
C12—C13—C14—C17	−178.02 (11)	N24—C24—C25—C26	177.18 (11)
C13—C14—C15—C16	−1.25 (19)	C23—C24—C25—C26	−2.60 (17)
C17—C14—C15—C16	177.93 (12)	C24—C25—C26—C21	0.89 (19)
C14—C15—C16—C11	−0.2 (2)	C22—C21—C26—C25	1.16 (18)
C12—C11—C16—C15	1.65 (19)	C1—C21—C26—C25	−175.79 (11)
N1—C11—C16—C15	−179.13 (12)	C23—C24—N24—C27	7.78 (17)
C15—C14—C17—O17	−3.32 (18)	C25—C24—N24—C27	−171.99 (11)
C13—C14—C17—O17	175.83 (12)	C23—C24—N24—C29	179.84 (11)
C15—C14—C17—C18	178.17 (12)	C25—C24—N24—C29	0.07 (18)
C13—C14—C17—C18	−2.68 (18)	C24—N24—C27—C28	−90.03 (14)
N1—C1—C21—C26	179.07 (11)	C29—N24—C27—C28	97.39 (13)
N1—C1—C21—C22	2.27 (18)	C24—N24—C29—C30	−86.08 (14)
C26—C21—C22—O22	178.75 (11)	C27—N24—C29—C30	86.47 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O22—H22···N1	0.96 (2)	1.72 (2)	2.6042 (13)	151.8 (18)
C16—H16···Cg1^i	0.95	2.81	3.65	148
C25—H25···Cg2^i	0.95	3.17	3.89	135

Symmetry code: (i) −x+1, y+1/2, −z+1/2.