Crystal structure of 2-benzamido-N-(2,2-di-eth-oxy-eth-yl)benzamide.

In the title compound, C20H24N2O4, both peptide bonds adopt a trans configuration with respect to the -N-H and -C=O groups. The dihedral angle between the aromatic rings is 53.58 (4)°. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond. The crystal packing is characterized by zigzag chains of N-H⋯O hydrogen-bonded mol-ecules running along the b-axis direction.

Related literature

For the synthesis of the title compound, see: Xingwen et al. (2007 ▸); Chandrika et al. (2008 ▸). Compounds with quinazoline scaffolds are of biological importance due to their pharmacological activities such as anti­microbial (Jantova et al., 2004 ▸; Shi et al., 2013 ▸), anti­tumorigenic (Kubo et al., 2005 ▸), anti­fungal (Dandia et al., 2005 ▸), anti­hyperglycemic (Ram et al., 2003 ▸), anti-inflammatory (Gineinah et al., 2002 ▸; Baba et al., 1996 ▸), anti­tumor (Forsch et al., 2002 ▸) and protein kinase inhibitor (Levitzky, 2003 ▸).

Experimental

Crystal data

C20H24N2O4

M = 356.41

Monoclinic,

a = 8.4901 (4) Å

b = 14.2281 (7) Å

c = 15.3864 (7) Å

β = 98.659 (4)°

V = 1837.46 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.36 × 0.35 × 0.32 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001 ▸) T min = 0.874, T max = 0.892

56243 measured reflections

5148 independent reflections

4676 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.110

S = 1.08

5148 reflections

244 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.18 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▸); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: XP (Sheldrick, 2008 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015003370/lh5750sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015003370/lh5750Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015003370/lh5750Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015003370/lh5750fig1.tif

A perspective view of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.

Click here for additional data file.

. DOI: 10.1107/S2056989015003370/lh5750fig2.tif

Crystal packing of the title compound. Hydrogen atoms bonded to C are omitted for clarity. Hydrogen bonds are shown as dashed lines.

CCDC reference: 1050003

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H24N2O4	F(000) = 760
Mr = 356.41	Dx = 1.288 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.4901 (4) Å	Cell parameters from 59538 reflections
b = 14.2281 (7) Å	θ = 3.6–29.9°
c = 15.3864 (7) Å	µ = 0.09 mm−1
β = 98.659 (4)°	T = 173 K
V = 1837.46 (15) Å3	Block, colourless
Z = 4	0.36 × 0.35 × 0.32 mm

Stoe IPDS II two-circle diffractometer	4676 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.065
ω scans	θmax = 29.7°, θmin = 3.6°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −11→10
Tmin = 0.874, Tmax = 0.892	k = −19→19
56243 measured reflections	l = −21→21
5148 independent reflections

Refinement on F2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.041	w = 1/[σ2(Fo2) + (0.0525P)2 + 0.4445P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.110	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.35 e Å−3
5148 reflections	Δρmin = −0.17 e Å−3
244 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.020 (2)

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.

	x	y	z	Uiso*/Ueq
N1	0.62897 (11)	0.11518 (6)	0.37268 (6)	0.02663 (18)
H1	0.6531 (19)	0.1522 (11)	0.4190 (10)	0.039 (4)*
N2	0.73335 (10)	0.39881 (6)	0.34983 (5)	0.02395 (17)
H2	0.7336 (17)	0.4150 (10)	0.2968 (10)	0.031 (3)*
O1	0.67588 (12)	−0.02751 (6)	0.31368 (5)	0.0385 (2)
O2	0.69514 (10)	0.28243 (5)	0.44371 (5)	0.02974 (17)
O3	0.80069 (8)	0.55548 (5)	0.53889 (5)	0.02611 (16)
O4	0.59596 (8)	0.56951 (5)	0.41902 (5)	0.02602 (16)
C1	0.67865 (13)	0.02429 (7)	0.37787 (7)	0.0271 (2)
C2	0.67557 (11)	0.31442 (7)	0.36759 (6)	0.02229 (18)
C3	0.81688 (11)	0.45736 (7)	0.41942 (6)	0.02321 (18)
H3A	0.8822	0.5043	0.3934	0.028*
H3B	0.8898	0.4176	0.4602	0.028*
C4	0.70242 (11)	0.50823 (7)	0.47073 (6)	0.02223 (18)
H4	0.6387	0.4601	0.4976	0.027*
C5	0.71605 (13)	0.59880 (9)	0.60186 (8)	0.0347 (2)
H5A	0.6615	0.5504	0.6327	0.042*
H5B	0.6347	0.6426	0.5721	0.042*
C6	0.83490 (14)	0.65147 (8)	0.66656 (7)	0.0330 (2)
H6A	0.7797	0.6819	0.7105	0.049*
H6B	0.9146	0.6075	0.6958	0.049*
H6C	0.8878	0.6993	0.6354	0.049*
C7	0.66672 (14)	0.64600 (9)	0.37833 (9)	0.0375 (3)
H7A	0.6954	0.6257	0.3212	0.045*
H7B	0.7649	0.6671	0.4164	0.045*
C8	0.54856 (18)	0.72486 (10)	0.36468 (11)	0.0473 (3)
H8A	0.5950	0.7779	0.3368	0.071*
H8B	0.4521	0.7035	0.3267	0.071*
H8C	0.5213	0.7447	0.4216	0.071*
C11	0.74040 (13)	−0.00903 (7)	0.46888 (7)	0.0277 (2)
C12	0.84330 (16)	−0.08571 (8)	0.47741 (9)	0.0391 (3)
H12	0.8685	−0.1164	0.4264	0.047*
C13	0.90937 (19)	−0.11757 (10)	0.56026 (10)	0.0493 (3)
H13	0.9823	−0.1686	0.5658	0.059*
C14	0.86936 (19)	−0.07526 (11)	0.63444 (9)	0.0509 (4)
H14	0.9139	−0.0975	0.6910	0.061*
C15	0.76431 (18)	−0.00032 (10)	0.62657 (8)	0.0425 (3)
H15	0.7361	0.0283	0.6779	0.051*
C16	0.69998 (14)	0.03331 (8)	0.54417 (7)	0.0319 (2)
H16	0.6285	0.0851	0.5391	0.038*
C21	0.56160 (11)	0.16374 (7)	0.29641 (6)	0.02321 (18)
C22	0.58342 (11)	0.26171 (7)	0.29212 (6)	0.02224 (18)
C23	0.51100 (13)	0.30950 (7)	0.21728 (7)	0.0273 (2)
H23	0.5245	0.3756	0.2136	0.033*
C24	0.41991 (13)	0.26268 (8)	0.14820 (7)	0.0301 (2)
H24	0.3724	0.2963	0.0976	0.036*
C25	0.39886 (12)	0.16645 (8)	0.15357 (7)	0.0291 (2)
H25	0.3359	0.1341	0.1067	0.035*
C26	0.46886 (13)	0.11722 (7)	0.22676 (7)	0.0274 (2)
H26	0.4538	0.0512	0.2297	0.033*

	U11	U22	U33	U12	U13	U23
N1	0.0370 (5)	0.0208 (4)	0.0209 (4)	−0.0003 (3)	0.0005 (3)	−0.0013 (3)
N2	0.0285 (4)	0.0242 (4)	0.0187 (4)	−0.0022 (3)	0.0021 (3)	−0.0009 (3)
O1	0.0569 (5)	0.0297 (4)	0.0287 (4)	0.0088 (4)	0.0053 (4)	−0.0057 (3)
O2	0.0428 (4)	0.0251 (3)	0.0196 (3)	−0.0033 (3)	−0.0007 (3)	0.0001 (3)
O3	0.0214 (3)	0.0309 (4)	0.0254 (3)	−0.0009 (3)	0.0015 (3)	−0.0082 (3)
O4	0.0204 (3)	0.0267 (3)	0.0302 (4)	0.0001 (3)	0.0013 (3)	0.0035 (3)
C1	0.0332 (5)	0.0230 (4)	0.0253 (4)	−0.0003 (4)	0.0053 (4)	−0.0003 (3)
C2	0.0241 (4)	0.0217 (4)	0.0204 (4)	0.0022 (3)	0.0013 (3)	−0.0020 (3)
C3	0.0213 (4)	0.0237 (4)	0.0241 (4)	−0.0017 (3)	0.0018 (3)	−0.0034 (3)
C4	0.0206 (4)	0.0228 (4)	0.0227 (4)	−0.0014 (3)	0.0015 (3)	−0.0015 (3)
C5	0.0279 (5)	0.0443 (6)	0.0321 (5)	−0.0004 (4)	0.0054 (4)	−0.0143 (5)
C6	0.0389 (6)	0.0293 (5)	0.0308 (5)	−0.0042 (4)	0.0051 (4)	−0.0078 (4)
C7	0.0303 (5)	0.0354 (6)	0.0472 (7)	0.0008 (4)	0.0070 (5)	0.0155 (5)
C8	0.0459 (7)	0.0348 (6)	0.0597 (8)	0.0072 (5)	0.0027 (6)	0.0140 (6)
C11	0.0333 (5)	0.0225 (4)	0.0268 (5)	−0.0040 (4)	0.0035 (4)	0.0026 (3)
C12	0.0471 (7)	0.0298 (5)	0.0412 (6)	0.0055 (5)	0.0093 (5)	0.0092 (5)
C13	0.0513 (8)	0.0415 (7)	0.0539 (8)	0.0059 (6)	0.0043 (6)	0.0229 (6)
C14	0.0593 (8)	0.0510 (8)	0.0384 (7)	−0.0101 (6)	−0.0055 (6)	0.0217 (6)
C15	0.0573 (8)	0.0435 (6)	0.0262 (5)	−0.0135 (6)	0.0042 (5)	0.0042 (5)
C16	0.0392 (6)	0.0288 (5)	0.0277 (5)	−0.0065 (4)	0.0048 (4)	−0.0001 (4)
C21	0.0257 (4)	0.0237 (4)	0.0204 (4)	0.0009 (3)	0.0039 (3)	−0.0019 (3)
C22	0.0238 (4)	0.0228 (4)	0.0197 (4)	0.0009 (3)	0.0021 (3)	−0.0021 (3)
C23	0.0311 (5)	0.0251 (4)	0.0240 (4)	0.0007 (4)	−0.0014 (4)	0.0003 (3)
C24	0.0307 (5)	0.0343 (5)	0.0231 (4)	0.0019 (4)	−0.0032 (4)	0.0002 (4)
C25	0.0271 (5)	0.0353 (5)	0.0238 (4)	−0.0023 (4)	0.0003 (4)	−0.0070 (4)
C26	0.0310 (5)	0.0254 (4)	0.0256 (4)	−0.0037 (4)	0.0034 (4)	−0.0051 (4)

N1—C1	1.3589 (13)	C7—H7B	0.9900
N1—C21	1.4069 (12)	C8—H8A	0.9800
N1—H1	0.886 (16)	C8—H8B	0.9800
N2—C2	1.3406 (12)	C8—H8C	0.9800
N2—C3	1.4542 (12)	C11—C12	1.3915 (16)
N2—H2	0.848 (15)	C11—C16	1.3937 (15)
O1—C1	1.2296 (13)	C12—C13	1.3892 (18)
O2—C2	1.2441 (11)	C12—H12	0.9500
O3—C4	1.4088 (11)	C13—C14	1.377 (2)
O3—C5	1.4299 (13)	C13—H13	0.9500
O4—C4	1.4120 (11)	C14—C15	1.384 (2)
O4—C7	1.4319 (13)	C14—H14	0.9500
C1—C11	1.4965 (14)	C15—C16	1.3878 (16)
C2—C22	1.4998 (12)	C15—H15	0.9500
C3—C4	1.5240 (13)	C16—H16	0.9500
C3—H3A	0.9900	C21—C26	1.3973 (13)
C3—H3B	0.9900	C21—C22	1.4091 (13)
C4—H4	1.0000	C22—C23	1.3976 (13)
C5—C6	1.5061 (15)	C23—C24	1.3871 (14)
C5—H5A	0.9900	C23—H23	0.9500
C5—H5B	0.9900	C24—C25	1.3850 (16)
C6—H6A	0.9800	C24—H24	0.9500
C6—H6B	0.9800	C25—C26	1.3821 (15)
C6—H6C	0.9800	C25—H25	0.9500
C7—C8	1.4987 (17)	C26—H26	0.9500
C7—H7A	0.9900
C1—N1—C21	126.87 (8)	H7A—C7—H7B	108.4
C1—N1—H1	119.1 (10)	C7—C8—H8A	109.5
C21—N1—H1	113.3 (10)	C7—C8—H8B	109.5
C2—N2—C3	121.06 (8)	H8A—C8—H8B	109.5
C2—N2—H2	119.5 (10)	C7—C8—H8C	109.5
C3—N2—H2	118.8 (10)	H8A—C8—H8C	109.5
C4—O3—C5	114.11 (7)	H8B—C8—H8C	109.5
C4—O4—C7	116.14 (8)	C12—C11—C16	119.35 (10)
O1—C1—N1	123.70 (10)	C12—C11—C1	117.59 (10)
O1—C1—C11	121.56 (9)	C16—C11—C1	123.06 (10)
N1—C1—C11	114.73 (9)	C13—C12—C11	120.23 (13)
O2—C2—N2	121.22 (9)	C13—C12—H12	119.9
O2—C2—C22	121.74 (9)	C11—C12—H12	119.9
N2—C2—C22	117.02 (8)	C14—C13—C12	120.12 (13)
N2—C3—C4	112.03 (8)	C14—C13—H13	119.9
N2—C3—H3A	109.2	C12—C13—H13	119.9
C4—C3—H3A	109.2	C13—C14—C15	120.03 (12)
N2—C3—H3B	109.2	C13—C14—H14	120.0
C4—C3—H3B	109.2	C15—C14—H14	120.0
H3A—C3—H3B	107.9	C14—C15—C16	120.36 (13)
O3—C4—O4	112.45 (8)	C14—C15—H15	119.8
O3—C4—C3	105.07 (7)	C16—C15—H15	119.8
O4—C4—C3	113.91 (8)	C15—C16—C11	119.87 (12)
O3—C4—H4	108.4	C15—C16—H16	120.1
O4—C4—H4	108.4	C11—C16—H16	120.1
C3—C4—H4	108.4	C26—C21—N1	121.23 (9)
O3—C5—C6	107.89 (9)	C26—C21—C22	119.70 (9)
O3—C5—H5A	110.1	N1—C21—C22	119.02 (8)
C6—C5—H5A	110.1	C23—C22—C21	118.38 (9)
O3—C5—H5B	110.1	C23—C22—C2	120.54 (8)
C6—C5—H5B	110.1	C21—C22—C2	121.02 (8)
H5A—C5—H5B	108.4	C24—C23—C22	121.54 (9)
C5—C6—H6A	109.5	C24—C23—H23	119.2
C5—C6—H6B	109.5	C22—C23—H23	119.2
H6A—C6—H6B	109.5	C25—C24—C23	119.41 (9)
C5—C6—H6C	109.5	C25—C24—H24	120.3
H6A—C6—H6C	109.5	C23—C24—H24	120.3
H6B—C6—H6C	109.5	C26—C25—C24	120.41 (9)
O4—C7—C8	108.32 (10)	C26—C25—H25	119.8
O4—C7—H7A	110.0	C24—C25—H25	119.8
C8—C7—H7A	110.0	C25—C26—C21	120.56 (9)
O4—C7—H7B	110.0	C25—C26—H26	119.7
C8—C7—H7B	110.0	C21—C26—H26	119.7
C21—N1—C1—O1	2.80 (18)	C13—C14—C15—C16	−0.7 (2)
C21—N1—C1—C11	−177.98 (9)	C14—C15—C16—C11	0.47 (19)
C3—N2—C2—O2	−1.91 (14)	C12—C11—C16—C15	0.99 (17)
C3—N2—C2—C22	176.69 (8)	C1—C11—C16—C15	−178.76 (11)
C2—N2—C3—C4	−78.73 (11)	C1—N1—C21—C26	31.59 (16)
C5—O3—C4—O4	62.87 (11)	C1—N1—C21—C22	−150.91 (10)
C5—O3—C4—C3	−172.70 (9)	C26—C21—C22—C23	−0.19 (14)
C7—O4—C4—O3	57.49 (11)	N1—C21—C22—C23	−177.73 (9)
C7—O4—C4—C3	−61.91 (11)	C26—C21—C22—C2	176.98 (9)
N2—C3—C4—O3	175.66 (8)	N1—C21—C22—C2	−0.56 (14)
N2—C3—C4—O4	−60.83 (10)	O2—C2—C22—C23	155.43 (10)
C4—O3—C5—C6	−176.28 (9)	N2—C2—C22—C23	−23.16 (13)
C4—O4—C7—C8	−153.25 (10)	O2—C2—C22—C21	−21.68 (14)
O1—C1—C11—C12	21.90 (16)	N2—C2—C22—C21	159.73 (9)
N1—C1—C11—C12	−157.34 (10)	C21—C22—C23—C24	−0.21 (15)
O1—C1—C11—C16	−158.35 (11)	C2—C22—C23—C24	−177.39 (10)
N1—C1—C11—C16	22.41 (15)	C22—C23—C24—C25	0.54 (16)
C16—C11—C12—C13	−2.25 (18)	C23—C24—C25—C26	−0.49 (17)
C1—C11—C12—C13	177.51 (12)	C24—C25—C26—C21	0.10 (16)
C11—C12—C13—C14	2.1 (2)	N1—C21—C26—C25	177.72 (10)
C12—C13—C14—C15	−0.6 (2)	C22—C21—C26—C25	0.24 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.886 (16)	1.914 (15)	2.6434 (11)	138.6 (14)
N2—H2···O1i	0.848 (15)	2.132 (15)	2.9338 (12)	157.6 (13)

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
N1H1O2	0.886(16)	1.914(15)	2.6434(11)	138.6(14)
N2H2O1i	0.848(15)	2.132(15)	2.9338(12)	157.6(13)

Symmetry code: (i) .