Crystal structure of 3-(4-hy­droxy­phen­yl)-2-[(E)-2-phenyl­ethen­yl]quinazolin-4(3H)-one

Mierina, I.; Stepanovs, D.; Kuginyte, J.; Janichev, A.; Jure, M.

doi:10.1107/S2056989016004473

Crystal structure of 3-(4-hydroxyphenyl)-2-[(E)-2-phenylethenyl]quinazolin-4(3H)-one

I. Mierina, D. Stepanovs, J. Kuginyte, A. Janichev and M. Jure

The title compound consists of a substituted 2-[(E)-2-arylethenyl]-3-arylquinazolin-4(3H)-one skeleton. The substituents at the ethylene fragment are located in trans positions. In the crystal, molecules are connected via O—H

O hydrogen bonds forming a 2₁ helix propagating along the a-axis direction.

Keywords: crystal structure; 2,3-disubstituted quinazolin-4(3H)-one; styrylquinazolinone conjugation system; hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989016004473/su5288sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989016004473/su5288Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989016004473/su5288Isup3.cml Supplementary material

CCDC reference: 1468806

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.007 Å
R factor = 0.068
wR factor = 0.139
Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00664 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.098 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           5 Note
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  P21nb      Pna21   Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

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

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2011 (Burla et al., 2012); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2015 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

3-(4-Hydroxyphenyl)-2-[(E)-2-phenylethenyl]quinazolin-4(3H)-one top

Crystal data top

C₂₂H₁₆N₂O₂	D_x = 1.287 Mg m⁻³
M_r = 340.37	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁nb	Cell parameters from 6856 reflections
a = 5.3469 (2) Å	θ = 1.0–27.5°
b = 16.5139 (6) Å	µ = 0.08 mm⁻¹
c = 19.8885 (10) Å	T = 173 K
V = 1756.12 (13) Å³	Plate, colorless
Z = 4	0.22 × 0.18 × 0.09 mm
F(000) = 712

Data collection top

Nonius KappaCCD diffractometer	2236 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 3.2°
φ and ω scan	h = −6→6
3862 measured reflections	k = −21→21
3862 independent reflections	l = −25→25

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)] = 0.068	H-atom parameters constrained
wR(F²) = 0.139	w = 1/[σ²(F_o²) + (0.0478P)² + 0.3939P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3862 reflections	Δρ_max = 0.17 e Å⁻³
236 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.6956 (7)	0.7742 (2)	0.45545 (18)	0.0333 (9)
C2	0.8449 (8)	0.7044 (3)	0.4584 (2)	0.0317 (10)
N3	0.8479 (7)	0.6500 (2)	0.41192 (18)	0.0372 (9)
C4	0.6912 (9)	0.6013 (3)	0.3061 (2)	0.0436 (12)
H4	0.7956	0.5564	0.3096	0.052*
C5	0.5358 (9)	0.6089 (3)	0.2518 (2)	0.0476 (13)
H5	0.5349	0.5690	0.2188	0.057*
C6	0.3791 (11)	0.6756 (3)	0.2457 (3)	0.0564 (15)
H6	0.2738	0.6801	0.2086	0.068*
C7	0.3795 (12)	0.7346 (3)	0.2939 (3)	0.0588 (15)
H7	0.2750	0.7793	0.2895	0.071*
C8	0.5362 (10)	0.7885 (3)	0.4018 (3)	0.0435 (12)
C9	0.6946 (8)	0.6604 (3)	0.3564 (2)	0.0337 (11)
C10	0.5376 (9)	0.7278 (3)	0.3501 (2)	0.0372 (11)
O11	0.4054 (7)	0.8506 (2)	0.40120 (19)	0.0653 (12)
C12	0.7042 (8)	0.8360 (3)	0.5076 (2)	0.0315 (10)
C13	0.5181 (8)	0.8382 (3)	0.5557 (2)	0.0354 (11)
H13	0.3953	0.7983	0.5563	0.042*
C14	0.5143 (9)	0.8993 (3)	0.6027 (2)	0.0372 (11)
H14	0.3905	0.9002	0.6356	0.045*
C15	0.6941 (8)	0.9595 (3)	0.6013 (2)	0.0309 (10)
C16	0.8821 (8)	0.9566 (3)	0.5533 (2)	0.0344 (11)
H16	1.0059	0.9962	0.5528	0.041*
C17	0.8859 (8)	0.8951 (3)	0.5064 (2)	0.0339 (11)
H17	1.0110	0.8936	0.4739	0.041*
O18	0.6763 (7)	1.01968 (18)	0.64797 (15)	0.0426 (8)
H18	0.7583	1.0589	0.6356	0.064*
C19	0.9961 (7)	0.6928 (3)	0.5188 (2)	0.0338 (11)
H19	0.9602	0.7230	0.5570	0.041*
C20	1.1845 (8)	0.6398 (3)	0.5204 (2)	0.0341 (10)
H20	1.2220	0.6133	0.4804	0.041*
C21	1.3390 (9)	0.6191 (3)	0.5794 (2)	0.0361 (11)
C22	1.2883 (9)	0.6474 (3)	0.6437 (2)	0.0435 (12)
H22	1.1527	0.6816	0.6508	0.052*
C23	1.4371 (8)	0.6252 (3)	0.6973 (3)	0.0498 (15)
H23	1.4006	0.6441	0.7402	0.060*
C24	1.6404 (9)	0.5748 (3)	0.6875 (3)	0.0512 (14)
H24	1.7421	0.5605	0.7235	0.061*
C25	1.6909 (10)	0.5460 (3)	0.6243 (3)	0.0496 (13)
H25	1.8265	0.5117	0.6176	0.060*
C26	1.5421 (9)	0.5676 (3)	0.5706 (2)	0.0399 (12)
H26	1.5779	0.5475	0.5280	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0351 (19)	0.030 (2)	0.035 (2)	0.0014 (17)	−0.0054 (19)	−0.0034 (17)
C2	0.031 (2)	0.027 (2)	0.037 (3)	0.003 (2)	−0.004 (2)	−0.002 (2)
N3	0.041 (2)	0.033 (2)	0.037 (2)	0.0064 (18)	−0.0066 (19)	−0.0067 (19)
C4	0.050 (3)	0.038 (3)	0.042 (3)	0.003 (2)	−0.001 (3)	−0.007 (2)
C5	0.052 (3)	0.051 (4)	0.040 (3)	−0.011 (3)	−0.001 (3)	−0.013 (3)
C6	0.066 (3)	0.065 (4)	0.038 (3)	−0.002 (3)	−0.017 (3)	−0.007 (3)
C7	0.067 (3)	0.059 (4)	0.050 (3)	0.012 (3)	−0.021 (3)	−0.003 (3)
C8	0.045 (3)	0.041 (3)	0.043 (3)	0.004 (3)	−0.012 (3)	−0.001 (2)
C9	0.036 (2)	0.034 (3)	0.031 (3)	−0.001 (2)	−0.004 (2)	−0.002 (2)
C10	0.044 (2)	0.038 (3)	0.030 (3)	0.004 (2)	−0.006 (2)	−0.001 (2)
O11	0.081 (3)	0.055 (3)	0.060 (3)	0.029 (2)	−0.030 (2)	−0.010 (2)
C12	0.031 (2)	0.031 (3)	0.032 (3)	0.003 (2)	−0.003 (2)	−0.003 (2)
C13	0.036 (2)	0.029 (3)	0.041 (3)	−0.009 (2)	−0.001 (2)	0.004 (2)
C14	0.039 (2)	0.037 (3)	0.036 (3)	−0.002 (2)	0.006 (2)	0.003 (2)
C15	0.040 (2)	0.027 (3)	0.026 (2)	−0.003 (2)	−0.003 (2)	0.001 (2)
C16	0.034 (2)	0.033 (3)	0.036 (3)	−0.007 (2)	0.001 (2)	0.000 (2)
C17	0.032 (2)	0.036 (3)	0.034 (3)	−0.001 (2)	0.004 (2)	0.001 (2)
O18	0.062 (2)	0.0355 (19)	0.0304 (17)	−0.0100 (17)	0.0041 (16)	−0.0058 (16)
C19	0.038 (2)	0.029 (3)	0.034 (3)	−0.002 (2)	−0.006 (2)	−0.002 (2)
C20	0.040 (2)	0.027 (2)	0.035 (3)	−0.002 (2)	−0.005 (2)	0.000 (2)
C21	0.037 (2)	0.030 (3)	0.041 (3)	−0.007 (2)	−0.012 (2)	0.001 (2)
C22	0.041 (3)	0.045 (3)	0.044 (3)	−0.003 (2)	−0.008 (2)	−0.004 (3)
C23	0.054 (3)	0.060 (4)	0.036 (3)	−0.010 (3)	−0.009 (2)	0.002 (3)
C24	0.047 (3)	0.060 (4)	0.047 (4)	−0.009 (3)	−0.018 (2)	0.011 (3)
C25	0.038 (3)	0.051 (3)	0.059 (4)	0.001 (2)	−0.007 (3)	0.016 (3)
C26	0.039 (2)	0.040 (3)	0.041 (3)	−0.001 (2)	−0.003 (2)	0.003 (2)

Geometric parameters (Å, º) top

N1—C8	1.385 (6)	C14—H14	0.9300
N1—C2	1.404 (5)	C15—O18	1.364 (5)
N1—C12	1.455 (5)	C15—C16	1.387 (6)
C2—N3	1.289 (5)	C16—C17	1.379 (6)
C2—C19	1.459 (6)	C16—H16	0.9300
N3—C9	1.385 (5)	C17—H17	0.9300
C4—C5	1.368 (7)	O18—H18	0.8200
C4—C9	1.398 (6)	C19—C20	1.335 (6)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.390 (7)	C20—C21	1.475 (6)
C5—H5	0.9300	C20—H20	0.9300
C6—C7	1.367 (7)	C21—C22	1.389 (6)
C6—H6	0.9300	C21—C26	1.390 (6)
C7—C10	1.406 (7)	C22—C23	1.379 (6)
C7—H7	0.9300	C22—H22	0.9300
C8—O11	1.241 (6)	C23—C24	1.382 (7)
C8—C10	1.436 (6)	C23—H23	0.9300
C9—C10	1.400 (6)	C24—C25	1.370 (7)
C12—C17	1.378 (6)	C24—H24	0.9300
C12—C13	1.381 (6)	C25—C26	1.378 (7)
C13—C14	1.377 (6)	C25—H25	0.9300
C13—H13	0.9300	C26—H26	0.9300
C14—C15	1.383 (6)

C8—N1—C2	121.5 (4)	C15—C14—H14	119.9
C8—N1—C12	116.7 (4)	O18—C15—C14	117.4 (4)
C2—N1—C12	121.8 (3)	O18—C15—C16	123.0 (4)
N3—C2—N1	123.3 (4)	C14—C15—C16	119.6 (4)
N3—C2—C19	119.4 (4)	C17—C16—C15	120.1 (4)
N1—C2—C19	117.3 (4)	C17—C16—H16	119.9
C2—N3—C9	118.6 (4)	C15—C16—H16	119.9
C5—C4—C9	120.6 (5)	C12—C17—C16	120.0 (4)
C5—C4—H4	119.7	C12—C17—H17	120.0
C9—C4—H4	119.7	C16—C17—H17	120.0
C4—C5—C6	120.6 (5)	C15—O18—H18	109.5
C4—C5—H5	119.7	C20—C19—C2	121.6 (4)
C6—C5—H5	119.7	C20—C19—H19	119.2
C7—C6—C5	120.2 (5)	C2—C19—H19	119.2
C7—C6—H6	119.9	C19—C20—C21	126.5 (4)
C5—C6—H6	119.9	C19—C20—H20	116.8
C6—C7—C10	120.1 (5)	C21—C20—H20	116.8
C6—C7—H7	119.9	C22—C21—C26	118.3 (4)
C10—C7—H7	119.9	C22—C21—C20	123.1 (4)
O11—C8—N1	119.7 (5)	C26—C21—C20	118.7 (4)
O11—C8—C10	124.9 (5)	C23—C22—C21	120.6 (5)
N1—C8—C10	115.5 (4)	C23—C22—H22	119.7
N3—C9—C4	119.4 (4)	C21—C22—H22	119.7
N3—C9—C10	121.7 (4)	C22—C23—C24	120.3 (5)
C4—C9—C10	118.9 (4)	C22—C23—H23	119.9
C9—C10—C7	119.7 (4)	C24—C23—H23	119.9
C9—C10—C8	119.5 (4)	C25—C24—C23	119.6 (5)
C7—C10—C8	120.7 (5)	C25—C24—H24	120.2
C17—C12—C13	120.1 (4)	C23—C24—H24	120.2
C17—C12—N1	120.4 (4)	C24—C25—C26	120.4 (5)
C13—C12—N1	119.3 (4)	C24—C25—H25	119.8
C14—C13—C12	120.1 (4)	C26—C25—H25	119.8
C14—C13—H13	120.0	C25—C26—C21	120.8 (5)
C12—C13—H13	120.0	C25—C26—H26	119.6
C13—C14—C15	120.1 (4)	C21—C26—H26	119.6
C13—C14—H14	119.9

C8—N1—C2—N3	1.2 (7)	C8—N1—C12—C17	−95.4 (5)
C12—N1—C2—N3	−177.5 (4)	C2—N1—C12—C17	83.3 (5)
C8—N1—C2—C19	−176.7 (4)	C8—N1—C12—C13	80.1 (5)
C12—N1—C2—C19	4.7 (6)	C2—N1—C12—C13	−101.2 (5)
N1—C2—N3—C9	−0.6 (6)	C17—C12—C13—C14	−0.3 (6)
C19—C2—N3—C9	177.1 (4)	N1—C12—C13—C14	−175.8 (4)
C9—C4—C5—C6	0.2 (8)	C12—C13—C14—C15	1.1 (7)
C4—C5—C6—C7	0.2 (9)	C13—C14—C15—O18	178.2 (4)
C5—C6—C7—C10	−0.3 (9)	C13—C14—C15—C16	−1.8 (7)
C2—N1—C8—O11	179.4 (5)	O18—C15—C16—C17	−178.4 (4)
C12—N1—C8—O11	−1.9 (7)	C14—C15—C16—C17	1.6 (7)
C2—N1—C8—C10	−0.7 (6)	C13—C12—C17—C16	0.1 (6)
C12—N1—C8—C10	178.0 (4)	N1—C12—C17—C16	175.5 (4)
C2—N3—C9—C4	−178.7 (4)	C15—C16—C17—C12	−0.7 (7)
C2—N3—C9—C10	−0.3 (6)	N3—C2—C19—C20	17.8 (7)
C5—C4—C9—N3	178.0 (4)	N1—C2—C19—C20	−164.3 (4)
C5—C4—C9—C10	−0.5 (7)	C2—C19—C20—C21	−175.8 (4)
N3—C9—C10—C7	−178.0 (5)	C19—C20—C21—C22	6.9 (7)
C4—C9—C10—C7	0.4 (7)	C19—C20—C21—C26	−174.5 (4)
N3—C9—C10—C8	0.7 (7)	C26—C21—C22—C23	0.4 (7)
C4—C9—C10—C8	179.1 (4)	C20—C21—C22—C23	179.0 (4)
C6—C7—C10—C9	0.0 (8)	C21—C22—C23—C24	0.5 (7)
C6—C7—C10—C8	−178.7 (5)	C22—C23—C24—C25	−1.0 (7)
O11—C8—C10—C9	179.8 (5)	C23—C24—C25—C26	0.6 (8)
N1—C8—C10—C9	−0.2 (6)	C24—C25—C26—C21	0.3 (7)
O11—C8—C10—C7	−1.6 (8)	C22—C21—C26—C25	−0.8 (7)
N1—C8—C10—C7	178.5 (5)	C20—C21—C26—C25	−179.5 (4)

Hydrogen-bond geometry (Å, º) top

Cg3 and Cg4 are the centroids of the C12–C17 and C21–C26 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O18—H18···O11ⁱ	0.82	1.84	2.654 (5)	172
C4—H4···Cg4ⁱⁱ	0.94	2.96	3.829 (5)	157
C16—H16···Cg3ⁱ	0.94	2.95	3.646 (5)	133

Symmetry codes: (i) x+1/2, −y+2, −z+1; (ii) x−1/2, −y+1, −z+1.

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Crystal structure of 3-(4-hy­droxy­phen­yl)-2-[(E)-2-phenyl­ethen­yl]quinazolin-4(3H)-one

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure of 3-(4-hydroxyphenyl)-2-[(E)-2-phenylethenyl]quinazolin-4(3H)-one