3-(4-Methoxy­phen­yl)-1-(2-nitrophen­yl)prop-2-en-1-one

The title compound, C₁₆H₁₃NO₄, was prepared from 2-nitrylhypnone [systematic name: 1-(2-nitrophenyl)ethanone] and 4-methoxy­benzophenone by a Claisen–Schmidt condensation. The dihedral angle formed by the two benzene rings is 80.73 (2). The crystal packing is stabilized by inter­molecular C—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.124
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          3

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

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

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

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S1. Comment

Among flavonoids, chalcones have been identified as interesting compounds having multiple biological actions which include antiinflammatory (Hsieh et al.,1998)and antioxidant (Anto et al.,1994). Of particular interest, the effectiveness of chalcones againest cancer has been investigated (De Vincenzo et al., 2000; Dimmock et al.,1998). As part of our search for new biologically active compounds we synthesized the title compound(I) and report its crystal structure herein.

Scheme I

The molecule (I) (Fig. 1) is made up of two essentially planar segments. The atoms O1, C1,C2, C3, C4, C5, C6 and C7 make up one segment (largest deviation being 0.018Å for C6) with the nitro phenyl group being the second planar segment (largest deviation 0.0177Å for N1).The dihedral angel formed by the two planes is 81.07 (2)°. All of the bond lengths and bond angles are in normal ranges and comparable to those found in a related structure (Fun et al., 2008). In the crystal structure, the molecules are stacked along the b axis and linked via C—H···O interactions (Fig. 2).

Related literature

For the biological activity of chalcones, see: Anto et al. (1994); De Vincenzo et al. (2000); Dimmock et al. (1998); Hsieh et al. (1998).For a related structure, see: Fun et al. (2008);

S2. Experimental

The title compound(I) was prepared by the process as following: A mixture of the 2-nitrylhypnone (0.02 mol), 4-methoxybenzophenone(0.02 mol) and 10%NaOH(10 ml) was stirred in ethanol(30 ml) for 3 h to afford the title compound(yield78%).Single crystals suitable for X-ray measurements were obtained by recrystallization from ethyl acetate at room temperature.

S3. Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H distances of0.93–0.96 Å, and with U_iso(H) = 1.2U_eq of the parent atoms.

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The crystal packing of the title compound,viewed along a axis.

3-(4-Methoxyphenyl)-1-(2-nitrophenyl)prop-2-en-1-one

Crystal data

C16H13NO4	F(000) = 592
Mr = 283.27	Dx = 1.380 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2667 reflections
a = 11.594 (2) Å	θ = 3.1–27.5°
b = 7.7736 (16) Å	µ = 0.10 mm^−1
c = 15.174 (3) Å	T = 293 K
β = 94.59 (3)°	Bar, yellow
V = 1363.1 (5) Å^3	0.21 × 0.18 × 0.10 mm
Z = 4

Data collection

Bruker sMART CCD area-detector diffractometer	2667 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
Graphite monochromator	θmax = 27.5°, θmin = 3.1°
phi and ω scans	h = −15→15
12773 measured reflections	k = −10→8
3107 independent reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0747P)^2 + 0.157P] where P = (Fo^2 + 2Fc^2)/3
3107 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

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
C8	0.72395 (9)	0.18277 (14)	0.22201 (7)	0.0385 (2)
H8A	0.7810	0.2655	0.2340	0.046*
O4	0.82958 (9)	0.02414 (13)	0.02294 (6)	0.0603 (3)
C5	0.63411 (9)	0.17369 (13)	0.28408 (7)	0.0371 (2)
N1	1.07316 (9)	0.10395 (13)	0.16402 (6)	0.0447 (2)
C2	0.46388 (9)	0.17332 (14)	0.40548 (8)	0.0402 (3)
C7	0.44279 (10)	0.09466 (16)	0.32265 (8)	0.0482 (3)
H7A	0.3714	0.0436	0.3073	0.058*
O3	1.01265 (9)	−0.02297 (12)	0.16921 (7)	0.0611 (3)
C16	0.85299 (10)	0.42736 (15)	0.08146 (8)	0.0442 (3)
H16A	0.7755	0.4334	0.0604	0.053*
C11	0.90152 (9)	0.26829 (14)	0.10358 (7)	0.0359 (2)
C12	1.01784 (9)	0.26616 (13)	0.13472 (7)	0.0362 (2)
C6	0.52710 (10)	0.09263 (15)	0.26394 (8)	0.0445 (3)
H6A	0.5130	0.0366	0.2100	0.053*
C13	1.08378 (10)	0.41407 (16)	0.14300 (8)	0.0454 (3)
H13A	1.1615	0.4087	0.1636	0.054*
C9	0.73401 (10)	0.08635 (15)	0.15007 (8)	0.0435 (3)
H9A	0.6811	−0.0023	0.1384	0.052*
C14	1.03253 (12)	0.57038 (15)	0.12026 (9)	0.0514 (3)
H14A	1.0760	0.6710	0.1254	0.062*
C4	0.65192 (9)	0.25538 (14)	0.36590 (8)	0.0414 (3)
H4A	0.7213	0.3129	0.3799	0.050*
O2	1.17769 (9)	0.10328 (15)	0.18354 (8)	0.0719 (3)
C10	0.82364 (10)	0.11242 (15)	0.08857 (7)	0.0409 (3)
C15	0.91755 (12)	0.57743 (15)	0.09011 (9)	0.0493 (3)
H15A	0.8831	0.6828	0.0755	0.059*
C3	0.56915 (10)	0.25320 (14)	0.42687 (8)	0.0410 (3)
H3A	0.5842	0.3051	0.4818	0.049*
O1	0.37527 (8)	0.16582 (14)	0.45895 (6)	0.0582 (3)
C1	0.39013 (13)	0.24330 (19)	0.54405 (9)	0.0596 (4)
H1A	0.3210	0.2283	0.5740	0.089*
H1B	0.4054	0.3639	0.5378	0.089*
H1C	0.4540	0.1900	0.5778	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C8	0.0357 (5)	0.0373 (5)	0.0419 (5)	−0.0036 (4)	−0.0006 (4)	0.0031 (4)
O4	0.0715 (6)	0.0603 (6)	0.0498 (5)	−0.0125 (5)	0.0103 (4)	−0.0185 (4)
C5	0.0369 (5)	0.0338 (5)	0.0400 (5)	−0.0028 (4)	0.0002 (4)	0.0032 (4)
N1	0.0496 (5)	0.0450 (5)	0.0397 (5)	0.0120 (4)	0.0042 (4)	−0.0005 (4)
C2	0.0387 (5)	0.0357 (5)	0.0467 (6)	−0.0029 (4)	0.0060 (4)	0.0029 (4)
C7	0.0404 (6)	0.0522 (7)	0.0516 (7)	−0.0158 (5)	0.0010 (5)	−0.0042 (5)
O3	0.0728 (6)	0.0398 (5)	0.0711 (6)	0.0075 (4)	0.0090 (5)	0.0099 (4)
C16	0.0426 (6)	0.0422 (6)	0.0481 (6)	0.0065 (4)	0.0056 (5)	0.0045 (5)
C11	0.0386 (5)	0.0361 (5)	0.0338 (5)	0.0004 (4)	0.0068 (4)	−0.0003 (4)
C12	0.0396 (5)	0.0365 (5)	0.0330 (5)	0.0047 (4)	0.0061 (4)	−0.0024 (4)
C6	0.0438 (6)	0.0472 (6)	0.0419 (6)	−0.0112 (5)	−0.0004 (5)	−0.0041 (5)
C13	0.0394 (5)	0.0485 (7)	0.0487 (6)	−0.0032 (5)	0.0060 (5)	−0.0088 (5)
C9	0.0432 (6)	0.0406 (6)	0.0466 (6)	−0.0093 (4)	0.0018 (5)	−0.0011 (5)
C14	0.0590 (7)	0.0378 (6)	0.0590 (7)	−0.0104 (5)	0.0145 (6)	−0.0077 (5)
C4	0.0349 (5)	0.0418 (6)	0.0467 (6)	−0.0067 (4)	−0.0012 (4)	−0.0029 (5)
O2	0.0501 (6)	0.0756 (7)	0.0877 (8)	0.0208 (5)	−0.0089 (5)	0.0045 (6)
C10	0.0440 (6)	0.0387 (6)	0.0396 (5)	−0.0008 (4)	0.0007 (4)	−0.0014 (4)
C15	0.0618 (7)	0.0337 (6)	0.0537 (7)	0.0077 (5)	0.0134 (6)	0.0041 (5)
C3	0.0406 (6)	0.0400 (6)	0.0417 (5)	−0.0026 (4)	−0.0006 (4)	−0.0044 (4)
O1	0.0492 (5)	0.0682 (6)	0.0593 (5)	−0.0160 (4)	0.0177 (4)	−0.0100 (5)
C1	0.0642 (8)	0.0620 (8)	0.0548 (7)	0.0018 (6)	0.0188 (6)	−0.0020 (6)

Geometric parameters (Å, º)

C8—C9	1.3369 (17)	C11—C10	1.5174 (15)
C8—C5	1.4609 (16)	C12—C13	1.3809 (16)
C8—H8A	0.9300	C6—H6A	0.9300
O4—C10	1.2159 (15)	C13—C14	1.3841 (18)
C5—C4	1.3951 (16)	C13—H13A	0.9300
C5—C6	1.4031 (15)	C9—C10	1.4653 (17)
N1—O3	1.2168 (14)	C9—H9A	0.9300
N1—O2	1.2242 (15)	C14—C15	1.3753 (19)
N1—C12	1.4674 (14)	C14—H14A	0.9300
C2—O1	1.3604 (14)	C4—C3	1.3854 (17)
C2—C3	1.3846 (16)	C4—H4A	0.9300
C2—C7	1.4015 (17)	C15—H15A	0.9300
C7—C6	1.3743 (18)	C3—H3A	0.9300
C7—H7A	0.9300	O1—C1	1.4227 (17)
C16—C15	1.3866 (18)	C1—H1A	0.9600
C16—C11	1.3885 (15)	C1—H1B	0.9600
C16—H16A	0.9300	C1—H1C	0.9600
C11—C12	1.3929 (15)
C9—C8—C5	127.78 (10)	C12—C13—H13A	120.5
C9—C8—H8A	116.1	C14—C13—H13A	120.5
C5—C8—H8A	116.1	C8—C9—C10	123.72 (10)
C4—C5—C6	117.62 (10)	C8—C9—H9A	118.1
C4—C5—C8	119.30 (9)	C10—C9—H9A	118.1
C6—C5—C8	123.02 (10)	C15—C14—C13	120.22 (11)
O3—N1—O2	123.06 (11)	C15—C14—H14A	119.9
O3—N1—C12	118.43 (10)	C13—C14—H14A	119.9
O2—N1—C12	118.50 (11)	C3—C4—C5	121.84 (10)
O1—C2—C3	124.96 (11)	C3—C4—H4A	119.1
O1—C2—C7	115.49 (10)	C5—C4—H4A	119.1
C3—C2—C7	119.55 (11)	O4—C10—C9	122.22 (11)
C6—C7—C2	120.28 (10)	O4—C10—C11	120.10 (11)
C6—C7—H7A	119.9	C9—C10—C11	117.30 (9)
C2—C7—H7A	119.9	C14—C15—C16	119.96 (11)
C15—C16—C11	121.41 (11)	C14—C15—H15A	120.0
C15—C16—H16A	119.3	C16—C15—H15A	120.0
C11—C16—H16A	119.3	C2—C3—C4	119.58 (10)
C16—C11—C12	117.07 (10)	C2—C3—H3A	120.2
C16—C11—C10	116.75 (10)	C4—C3—H3A	120.2
C12—C11—C10	126.14 (9)	C2—O1—C1	118.75 (10)
C13—C12—C11	122.33 (10)	O1—C1—H1A	109.5
C13—C12—N1	117.55 (10)	O1—C1—H1B	109.5
C11—C12—N1	120.05 (10)	H1A—C1—H1B	109.5
C7—C6—C5	121.06 (11)	O1—C1—H1C	109.5
C7—C6—H6A	119.5	H1A—C1—H1C	109.5
C5—C6—H6A	119.5	H1B—C1—H1C	109.5
C12—C13—C14	119.00 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O1^i	0.93	2.51	3.249 (1)	136
C14—H14A···O3^ii	0.93	2.59	3.259 (2)	129

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