Diethyl 2-[(N-benzyl-N-methyl-amino)(phen-yl)meth-yl]propane-dioate.

In the title compound, C(22)H(27)NO(4), the mean planes of the two benzene rings form a dihedral angle of 73.54 (13)°. One of the methyl groups is disordered over two sites, with site occupation factors of 0.47 (15) and 0.53 (15). The crystal packing is controlled by van der Waals forces and a possible C-H⋯O inter-action, forming a chain running parallel to the a axis.

Related literature

For related compounds displaying biological activity, see: Dayam et al. (2007 ▶); Patil et al. (2007 ▶); Ramkumar et al. (2008 ▶); Sechi et al. (2009a ▶,b ▶); Zeng et al. (2008a ▶,b ▶). For the synthetic procedure, see: Pommier & Neamati (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H27NO4

M = 369.45

Monoclinic,

a = 9.3074 (2) Å

b = 5.9077 (1) Å

c = 37.0971 (7) Å

β = 92.999 (1)°

V = 2037.00 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.24 × 0.20 × 0.13 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

25575 measured reflections

4138 independent reflections

3411 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.159

S = 1.25

4138 reflections

257 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810007506/pv2262sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007506/pv2262Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H27NO4	F(000) = 792
Mr = 369.45	Dx = 1.205 Mg m−3
Monoclinic, P21/c	Melting point = 380–382 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.3074 (2) Å	Cell parameters from 3214 reflections
b = 5.9077 (1) Å	θ = 1.9–25.3°
c = 37.0971 (7) Å	µ = 0.08 mm−1
β = 92.999 (1)°	T = 296 K
V = 2037.00 (7) Å3	Block, colourless
Z = 4	0.24 × 0.20 × 0.13 mm

Bruker X8 APEXII CCD area-detector diffractometer	3411 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
graphite	θmax = 26.4°, θmin = 1.1°
φ and ω scans	h = −11→11
25575 measured reflections	k = −7→7
4138 independent reflections	l = −46→46

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.25	w = 1/[σ2(Fo2) + (0.0364P)2 + 1.9835P] where P = (Fo2 + 2Fc2)/3
4138 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.27 e Å−3
1 restraint	Δρmin = −0.26 e Å−3

Experimental. Yield = 78% (1.24 g). Rf = 0.45 (ether/hexane:1/1). Mp = 380-382 K.IR Spectroscopic (KBr, ν cm-1) analysis: 2860/2984 (C—H);1745 (CO); 1216/1301 (C—O); 1584/1601 (C=C), 1138, 1021.NMR analysis: 1H-NMR (250 MHz, CDCl3) δ (ppm): 7.2-7.4(m, 10H, aromat), 4.65 (d, H, Ph—C3H, 3J = 12.15 Hz), 4.01 (dq, 2HAB, OCH2CH3, 2JAB = 14.34 Hz, 3J =7.06 Hz), 4.35 (dq, 2HAB, OCH2CH3, 2JAB = 14.34 Hz,3J = 7.06 Hz), 4.32 (d, H, C2H(CO2Et)2 , 3J = 12.20 Hz), 3.5 (d, 1H, CH2Ph, 3J = 13.2 Hz), 3.25 (d, 1H, CH2Ph, 3J = 13.5 Hz), 2.05 (s, 3H, CH3), 1.33 (t, 3H, OCH2CH3, 3J = 7.2 Hz), 1.01 (t, 3H, OCH2CH3, 3J = 7.2 Hz). 13C-NMR (250 MHz, CDCl3) δ (ppm): 167.97 (C=O), 167.93 (C=O), 133.4 (Cquat, C-(Ph), 132.6 (Cquat, CPhCH2), 126.91/128.03 (Ctert, 10CH aromt), 67.47 (Ctert, C3HPh), 61.24 -61.3 (2 C, 2CH2CH3, ester), 55.39 (Ctert, C2H-(CO2Et), 58.70 (Cses, CľH2N), 36.94 (Cter, CH3N), 14.15/13.73 ( 2 C, 2CH3, esters).. MS (IE) Calcd for [M]+ C22H27NO4: 369.45. [M+H]+. (m/z) = 370, [M—CH(CO2Et)2]+ (m/z) = 159 (100%).Elemental analysis for C22H27NO4 : Calc (Found): C 71.52 (71.48), H 7.37 (7.35), N 3.79 (3.81).The purity of the compound was checked by determining its melting point (380-382 K). Suitable single crystal of malonate derivative (I) was obtained by recrystallization from ethanol. A colorless crystal of (I) having approximate dimensions of 0.24 x 0.20 x 0.09 mm was mounted on a glass fibre. All measurements were made in the φ and ω scans technique on a CCD X8 Bruker diffractometer with graphite monochromatized MoKα radiation at room temperature (296 (2) K).The data collection nominally covered a sphere of reciprocal space, by a combination of five sets of exposures; each set had a different φ angle for the crystal and each exposure covered 0.5° in ω and 30 seconds in time. The crystal-to-detector distance was 37.5 mm.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.4969 (3)	0.3979 (4)	0.18855 (6)	0.0302 (5)
H1A	0.5442	0.5408	0.1841	0.036*
H1B	0.5646	0.3016	0.2021	0.036*
C2	0.5612 (3)	0.3238 (4)	0.12647 (6)	0.0290 (5)
H2	0.5900	0.4832	0.1279	0.035*
C3	0.4123 (3)	0.0546 (4)	0.15968 (7)	0.0391 (6)
H3A	0.3777	−0.0094	0.1371	0.059*
H3B	0.3374	0.0494	0.1765	0.059*
H3C	0.4938	−0.0305	0.1691	0.059*
C4	0.4827 (3)	0.2917 (4)	0.08947 (6)	0.0318 (6)
H4	0.4493	0.1349	0.0870	0.038*
C5	0.5794 (3)	0.3490 (5)	0.05896 (6)	0.0354 (6)
C6	0.3536 (3)	0.4517 (5)	0.08739 (6)	0.0402 (7)
C11	0.3667 (3)	0.4396 (4)	0.21050 (6)	0.0277 (5)
C12	0.3634 (3)	0.3693 (5)	0.24598 (7)	0.0379 (6)
H12	0.4411	0.2903	0.2565	0.045*
C13	0.2448 (3)	0.4158 (5)	0.26603 (7)	0.0453 (7)
H13	0.2434	0.3673	0.2899	0.054*
C14	0.1298 (3)	0.5327 (5)	0.25081 (7)	0.0404 (7)
H14	0.0509	0.5649	0.2643	0.048*
C15	0.1318 (3)	0.6024 (5)	0.21538 (7)	0.0388 (6)
H15	0.0536	0.6805	0.2049	0.047*
C16	0.2495 (3)	0.5565 (4)	0.19540 (6)	0.0328 (6)
H16	0.2500	0.6046	0.1715	0.039*
C21	0.6990 (3)	0.1854 (4)	0.13072 (6)	0.0274 (5)
C22	0.7136 (3)	−0.0263 (4)	0.11485 (6)	0.0306 (5)
H22	0.6362	−0.0897	0.1015	0.037*
C23	0.8421 (3)	−0.1431 (5)	0.11870 (7)	0.0380 (6)
H23	0.8507	−0.2839	0.1078	0.046*
C24	0.9581 (3)	−0.0524 (5)	0.13858 (7)	0.0396 (6)
H24	1.0448	−0.1308	0.1408	0.048*
C25	0.9443 (3)	0.1542 (5)	0.15501 (7)	0.0403 (7)
H25	1.0213	0.2151	0.1688	0.048*
C26	0.8162 (3)	0.2716 (5)	0.15109 (6)	0.0352 (6)
H26	0.8082	0.4115	0.1623	0.042*
C31	0.0998 (4)	0.4617 (8)	0.07836 (10)	0.0745 (12)
H31A	0.0644	0.4759	0.1024	0.089*	0.53
H31B	0.1156	0.6124	0.0690	0.089*	0.53
H31C	0.0277	0.3731	0.0900	0.089*	0.47
H31D	0.1145	0.5999	0.0922	0.089*	0.47
C32	0.0021 (6)	0.3502 (13)	0.05651 (16)	0.0556 (17)	0.53
H32A	−0.0853	0.4364	0.0542	0.083*	0.53
H32B	−0.0173	0.2047	0.0667	0.083*	0.53
H32C	0.0398	0.3305	0.0331	0.083*	0.53
C32B	0.0454 (7)	0.5197 (15)	0.04332 (18)	0.059 (2)	0.47
H32D	0.0514	0.3908	0.0277	0.088*	0.47
H32E	0.1010	0.6418	0.0342	0.088*	0.47
H32F	−0.0533	0.5659	0.0443	0.088*	0.47
C41	0.6429 (4)	0.2245 (6)	0.00078 (8)	0.0617 (10)
H41A	0.6915	0.3698	0.0009	0.074*
H41B	0.5837	0.2120	−0.0214	0.074*
C42	0.7512 (5)	0.0371 (8)	0.00302 (11)	0.0870 (13)
H42A	0.8178	0.0623	0.0233	0.131*
H42B	0.8025	0.0334	−0.0188	0.131*
H42C	0.7029	−0.1047	0.0060	0.131*
N1	0.4551 (2)	0.2901 (3)	0.15416 (5)	0.0284 (5)
O1	0.3600 (3)	0.6519 (4)	0.09128 (6)	0.0592 (6)
O2	0.2341 (2)	0.3345 (4)	0.07988 (5)	0.0529 (6)
O3	0.6643 (3)	0.5002 (4)	0.05932 (5)	0.0576 (6)
O4	0.5537 (2)	0.2080 (4)	0.03170 (5)	0.0509 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0356 (13)	0.0276 (13)	0.0275 (12)	−0.0006 (11)	0.0029 (10)	−0.0026 (10)
C2	0.0402 (14)	0.0208 (12)	0.0263 (11)	0.0010 (11)	0.0052 (10)	−0.0036 (10)
C3	0.0504 (16)	0.0299 (14)	0.0380 (14)	−0.0036 (13)	0.0112 (12)	−0.0053 (12)
C4	0.0401 (14)	0.0275 (13)	0.0277 (12)	0.0078 (11)	0.0007 (10)	−0.0033 (10)
C5	0.0488 (16)	0.0314 (15)	0.0260 (12)	0.0143 (13)	0.0012 (11)	−0.0011 (11)
C6	0.0539 (18)	0.0454 (18)	0.0209 (12)	0.0153 (15)	−0.0006 (11)	−0.0032 (12)
C11	0.0350 (13)	0.0221 (12)	0.0260 (11)	−0.0042 (10)	0.0035 (9)	−0.0055 (10)
C12	0.0437 (15)	0.0389 (15)	0.0311 (13)	0.0070 (13)	0.0022 (11)	0.0039 (11)
C13	0.0549 (17)	0.0533 (19)	0.0288 (13)	0.0034 (15)	0.0119 (12)	0.0065 (13)
C14	0.0393 (15)	0.0461 (17)	0.0370 (14)	0.0000 (13)	0.0124 (11)	−0.0046 (13)
C15	0.0362 (14)	0.0424 (16)	0.0379 (14)	0.0048 (13)	0.0024 (11)	−0.0014 (12)
C16	0.0414 (14)	0.0329 (14)	0.0244 (11)	0.0009 (12)	0.0037 (10)	0.0009 (10)
C21	0.0357 (13)	0.0242 (12)	0.0229 (11)	0.0001 (11)	0.0060 (9)	0.0038 (9)
C22	0.0324 (13)	0.0269 (13)	0.0320 (12)	0.0010 (11)	−0.0028 (10)	−0.0006 (10)
C23	0.0425 (15)	0.0295 (14)	0.0417 (14)	0.0065 (12)	−0.0018 (12)	0.0001 (12)
C24	0.0337 (14)	0.0449 (17)	0.0400 (14)	0.0060 (13)	−0.0009 (11)	0.0090 (13)
C25	0.0338 (14)	0.0526 (18)	0.0343 (13)	−0.0098 (13)	−0.0006 (11)	−0.0007 (13)
C26	0.0465 (15)	0.0309 (14)	0.0287 (12)	−0.0108 (12)	0.0078 (11)	−0.0039 (11)
C31	0.059 (2)	0.104 (3)	0.060 (2)	0.048 (2)	−0.0056 (17)	−0.011 (2)
C32	0.030 (3)	0.085 (5)	0.051 (3)	0.008 (3)	−0.005 (3)	−0.014 (3)
C32B	0.035 (3)	0.081 (6)	0.061 (4)	0.010 (4)	0.004 (3)	0.024 (4)
C41	0.102 (3)	0.053 (2)	0.0321 (15)	0.002 (2)	0.0242 (16)	−0.0109 (14)
C42	0.115 (3)	0.082 (3)	0.068 (2)	0.019 (3)	0.041 (2)	−0.011 (2)
N1	0.0364 (11)	0.0226 (10)	0.0265 (10)	0.0002 (9)	0.0063 (8)	−0.0030 (8)
O1	0.0856 (17)	0.0391 (13)	0.0525 (13)	0.0256 (12)	0.0007 (11)	−0.0037 (10)
O2	0.0466 (12)	0.0626 (15)	0.0481 (12)	0.0262 (11)	−0.0087 (9)	−0.0141 (11)
O3	0.0867 (16)	0.0475 (13)	0.0407 (11)	−0.0182 (13)	0.0234 (11)	−0.0123 (10)
O4	0.0759 (15)	0.0480 (13)	0.0296 (9)	−0.0057 (11)	0.0112 (9)	−0.0109 (9)

C1—N1	1.460 (3)	C21—C22	1.392 (3)
C1—C11	1.515 (3)	C22—C23	1.382 (3)
C1—H1A	0.9700	C22—H22	0.9300
C1—H1B	0.9700	C23—C24	1.383 (4)
C2—N1	1.475 (3)	C23—H23	0.9300
C2—C21	1.522 (3)	C24—C25	1.373 (4)
C2—C4	1.533 (3)	C24—H24	0.9300
C2—H2	0.9800	C25—C26	1.380 (4)
C3—N1	1.464 (3)	C25—H25	0.9300
C3—H3A	0.9600	C26—H26	0.9300
C3—H3B	0.9600	C31—C32	1.357 (6)
C3—H3C	0.9600	C31—C32B	1.412 (7)
C4—C5	1.521 (4)	C31—O2	1.457 (4)
C4—C6	1.528 (4)	C31—H31A	0.9700
C4—H4	0.9800	C31—H31B	0.9700
C5—O3	1.192 (3)	C31—H31C	0.9700
C5—O4	1.323 (3)	C31—H31D	0.9700
C6—O1	1.192 (3)	C32—H31C	1.2600
C6—O2	1.327 (4)	C32—H32A	0.9600
C11—C12	1.382 (3)	C32—H32B	0.9600
C11—C16	1.385 (3)	C32—H32C	0.9600
C12—C13	1.390 (4)	C32B—H32D	0.9600
C12—H12	0.9300	C32B—H32E	0.9600
C13—C14	1.370 (4)	C32B—H32F	0.9600
C13—H13	0.9300	C41—O4	1.454 (3)
C14—C15	1.378 (4)	C41—C42	1.497 (5)
C14—H14	0.9300	C41—H41A	0.9700
C15—C16	1.381 (4)	C41—H41B	0.9700
C15—H15	0.9300	C42—H42A	0.9600
C16—H16	0.9300	C42—H42B	0.9600
C21—C26	1.392 (3)	C42—H42C	0.9600
N1—C1—C11	110.89 (19)	C23—C24—H24	120.2
N1—C1—H1A	109.5	C24—C25—C26	120.0 (2)
C11—C1—H1A	109.5	C24—C25—H25	120.0
N1—C1—H1B	109.5	C26—C25—H25	120.0
C11—C1—H1B	109.5	C25—C26—C21	121.5 (2)
H1A—C1—H1B	108.0	C25—C26—H26	119.3
N1—C2—C21	116.50 (19)	C21—C26—H26	119.3
N1—C2—C4	107.57 (19)	C32—C31—C32B	51.0 (4)
C21—C2—C4	112.69 (19)	C32—C31—O2	108.7 (4)
N1—C2—H2	106.5	C32B—C31—O2	115.3 (4)
C21—C2—H2	106.5	C32—C31—H31A	110.0
C4—C2—H2	106.5	C32B—C31—H31A	134.6
N1—C3—H3A	109.5	O2—C31—H31A	110.0
N1—C3—H3B	109.5	C32—C31—H31B	110.0
H3A—C3—H3B	109.5	C32B—C31—H31B	60.1
N1—C3—H3C	109.5	O2—C31—H31B	110.0
H3A—C3—H3C	109.5	H31A—C31—H31B	108.3
H3B—C3—H3C	109.5	C32—C31—H31C	63.0
C5—C4—C6	108.6 (2)	C32B—C31—H31C	108.5
C5—C4—C2	111.5 (2)	O2—C31—H31C	108.5
C6—C4—C2	107.79 (19)	H31A—C31—H31C	50.3
C5—C4—H4	109.6	H31B—C31—H31C	140.9
C6—C4—H4	109.6	C32—C31—H31D	142.7
C2—C4—H4	109.6	C32B—C31—H31D	108.4
O3—C5—O4	125.0 (2)	O2—C31—H31D	108.5
O3—C5—C4	125.2 (2)	H31A—C31—H31D	59.1
O4—C5—C4	109.8 (2)	H31B—C31—H31D	52.9
O1—C6—O2	125.4 (3)	H31C—C31—H31D	107.5
O1—C6—C4	125.0 (3)	C31—C32—H31C	43.3
O2—C6—C4	109.6 (2)	C31—C32—H32A	109.5
C12—C11—C16	118.6 (2)	H31C—C32—H32A	98.3
C12—C11—C1	121.4 (2)	C31—C32—H32B	109.5
C16—C11—C1	119.9 (2)	H31C—C32—H32B	74.8
C11—C12—C13	120.6 (2)	C31—C32—H32C	109.5
C11—C12—H12	119.7	H31C—C32—H32C	147.7
C13—C12—H12	119.7	C31—C32B—H32D	109.5
C14—C13—C12	120.2 (2)	C31—C32B—H32E	109.5
C14—C13—H13	119.9	H32D—C32B—H32E	109.5
C12—C13—H13	119.9	C31—C32B—H32F	109.5
C13—C14—C15	119.6 (2)	H32D—C32B—H32F	109.5
C13—C14—H14	120.2	H32E—C32B—H32F	109.5
C15—C14—H14	120.2	O4—C41—C42	108.5 (3)
C14—C15—C16	120.3 (3)	O4—C41—H41A	110.0
C14—C15—H15	119.9	C42—C41—H41A	110.0
C16—C15—H15	119.9	O4—C41—H41B	110.0
C15—C16—C11	120.7 (2)	C42—C41—H41B	110.0
C15—C16—H16	119.6	H41A—C41—H41B	108.4
C11—C16—H16	119.6	C41—C42—H42A	109.5
C26—C21—C22	117.9 (2)	C41—C42—H42B	109.5
C26—C21—C2	119.5 (2)	H42A—C42—H42B	109.5
C22—C21—C2	122.6 (2)	C41—C42—H42C	109.5
C23—C22—C21	120.5 (2)	H42A—C42—H42C	109.5
C23—C22—H22	119.7	H42B—C42—H42C	109.5
C21—C22—H22	119.7	C1—N1—C3	110.74 (19)
C22—C23—C24	120.6 (3)	C1—N1—C2	113.09 (19)
C22—C23—H23	119.7	C3—N1—C2	114.98 (19)
C24—C23—H23	119.7	C6—O2—C31	116.5 (3)
C25—C24—C23	119.5 (3)	C5—O4—C41	118.2 (2)
C25—C24—H24	120.2

D—H···A	D—H	H···A	D···A	D—H···A
C32—H32A···O3i	0.96	2.38	3.273 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C32—H32A⋯O3i	0.96	2.38	3.273 (3)	155

Symmetry code: (i) .