1-(4-Methoxy­phenyl)-2-(2-nitro­phenoxy)­propan-1-one

Vencato, I.; Ferri, P.H.; Santos, S.C.; Santos, L.S.; Lariucci, C.; Napolitano, H.B.

doi:10.1107/S1600536804030260

1-(4-Methoxyphenyl)-2-(2-nitrophenoxy)propan-1-one

I. Vencato, P. H. Ferri, S. C. Santos, L. S. Santos, C. Lariucci and H. B. Napolitano

The title compound, C₁₆H₁₅N₁O₅, is a β-ketoether derivative, closely related to natural 8.4′-oxyneolignans, which are of interest because of their antiprotozoal activity. The nitro group is not coplanar with the aromatic ring, as is shown by a torsion angle of 49.4 (3)°. The molecules are connected in the crystal structure by two non-classical intermolecular hydrogen bonds with C

O distances of 3.363 (3) and 3.274 (2) Å; repetition of these hydrogen bonds leads to the formation of sheets of molecules parallel to the (001) plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804030260/gh6006sup1.cif Contains datablocks global, II
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804030260/gh6006IIsup2.hkl Contains datablock II

CCDC reference: 259859

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Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.042
wR factor = 0.129
Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C1      ..       5.16 su
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors  for         N1

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

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

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

1-(4-Methoxyphenyl)-2-(2-nitrophenoxy)propan-1-one top

Crystal data top

C₁₆H₁₅NO₅	F(000) = 632
M_r = 301.29	D_x = 1.334 Mg m⁻³
Monoclinic, P12₁/c1	Melting point = 403–404 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 8.851 (2) Å	Cell parameters from 25 reflections
b = 9.858 (2) Å	θ = 10.4–13.6°
c = 17.255 (3) Å	µ = 0.10 mm⁻¹
β = 94.99 (3)°	T = 293 K
V = 1499.8 (5) Å³	Block, colourless
Z = 4	0.35 × 0.33 × 0.33 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	R_int = 0.023
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.3°
Graphite monochromator	h = −10→10
non–profiled ω/2θ scans	k = 0→11
2738 measured reflections	l = 0→20
2643 independent reflections	2 standard reflections every 120 min
2080 reflections with I > 2σ(I)	intensity decay: <1%

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0651P)² + 0.3965P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2643 reflections	Δρ_max = 0.25 e Å⁻³
206 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.056 (4)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.14241 (14)	0.93771 (13)	0.17171 (7)	0.0576 (4)
O2	0.10978 (15)	0.76576 (13)	0.29073 (8)	0.0607 (4)
O4	0.2464 (2)	0.9577 (2)	0.02752 (10)	0.1005 (6)
O5	0.4702 (2)	0.87703 (19)	0.05173 (11)	0.1018 (6)
N1	0.3620 (2)	0.94670 (19)	0.06865 (11)	0.0674 (5)
C1	0.3798 (2)	1.02035 (18)	0.14230 (10)	0.0514 (5)
C2	0.5114 (2)	1.0928 (2)	0.15909 (13)	0.0660 (6)
H2	0.5854	1.0945	0.1240	0.079*
C3	0.5330 (2)	1.1630 (3)	0.22829 (14)	0.0720 (6)
H3	0.624 (3)	1.212 (2)	0.2395 (14)	0.086*
C4	0.4232 (2)	1.1562 (2)	0.28001 (13)	0.0661 (6)
H4	0.4377	1.2025	0.3270	0.079*
C5	0.2924 (2)	1.0823 (2)	0.26354 (11)	0.0552 (5)
H5	0.2207	1.0781	0.2998	0.066*
C6	0.26663 (19)	1.01402 (17)	0.19345 (10)	0.0463 (4)
C7	0.0126 (2)	0.95223 (19)	0.21514 (10)	0.0491 (4)
H7	0.000 (2)	1.045 (2)	0.2281 (12)	0.059*
C8	0.02786 (18)	0.86543 (17)	0.28873 (10)	0.0455 (4)
C9	−0.06337 (18)	0.89992 (17)	0.35361 (10)	0.0450 (4)
C10	−0.1288 (2)	1.02644 (18)	0.36237 (11)	0.0532 (5)
H10	−0.1199	1.0924	0.3245	0.064*
C11	−0.2069 (2)	1.05634 (19)	0.42622 (11)	0.0564 (5)
H11	−0.2477	1.1424	0.4316	0.068*
C12	−0.2245 (2)	0.95849 (19)	0.48197 (10)	0.0520 (5)
C13	−0.1634 (2)	0.8298 (2)	0.47267 (11)	0.0618 (5)
H13	−0.1773	0.7624	0.5091	0.074*
C14	−0.0834 (2)	0.80189 (19)	0.41038 (11)	0.0558 (5)
H14	−0.0414	0.7161	0.4056	0.067*
C15	−0.3619 (3)	1.1076 (2)	0.55923 (12)	0.0709 (6)
H15A	−0.4106	1.1069	0.6068	0.106*
H15B	−0.4351	1.1291	0.5166	0.106*
H15C	−0.2828	1.1745	0.5625	0.106*
C16	−0.1215 (2)	0.9033 (3)	0.16219 (12)	0.0703 (6)
H16A	−0.1314	0.9579	0.1160	0.105*
H16B	−0.2122	0.9107	0.1887	0.105*
H16C	−0.1061	0.8103	0.1484	0.105*
O3	−0.29809 (17)	0.97659 (15)	0.54685 (8)	0.0679 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0607 (8)	0.0597 (8)	0.0553 (8)	−0.0129 (6)	0.0217 (6)	−0.0150 (6)
O2	0.0638 (8)	0.0514 (8)	0.0682 (9)	0.0117 (7)	0.0131 (6)	−0.0022 (6)
O4	0.1121 (14)	0.1365 (18)	0.0531 (10)	0.0006 (13)	0.0083 (10)	−0.0090 (10)
O5	0.1354 (16)	0.0846 (12)	0.0927 (13)	0.0260 (11)	0.0506 (11)	−0.0079 (10)
N1	0.0863 (13)	0.0687 (12)	0.0510 (10)	0.0004 (10)	0.0280 (9)	0.0063 (8)
C1	0.0604 (11)	0.0493 (10)	0.0466 (9)	0.0049 (8)	0.0167 (8)	0.0073 (8)
C2	0.0570 (12)	0.0714 (13)	0.0728 (14)	−0.0013 (10)	0.0231 (10)	0.0127 (11)
C3	0.0550 (12)	0.0798 (15)	0.0811 (15)	−0.0143 (11)	0.0045 (10)	0.0046 (12)
C4	0.0672 (12)	0.0693 (13)	0.0612 (12)	−0.0105 (10)	0.0028 (10)	−0.0051 (10)
C5	0.0582 (11)	0.0590 (11)	0.0502 (10)	−0.0052 (9)	0.0152 (8)	−0.0036 (8)
C6	0.0510 (9)	0.0412 (9)	0.0481 (9)	−0.0005 (8)	0.0119 (7)	0.0033 (7)
C7	0.0501 (10)	0.0481 (10)	0.0506 (10)	−0.0036 (8)	0.0130 (8)	−0.0024 (8)
C8	0.0424 (9)	0.0409 (9)	0.0532 (10)	−0.0044 (7)	0.0044 (7)	−0.0060 (8)
C9	0.0459 (9)	0.0429 (9)	0.0460 (9)	−0.0023 (7)	0.0031 (7)	−0.0014 (7)
C10	0.0607 (11)	0.0471 (10)	0.0534 (11)	0.0046 (8)	0.0134 (8)	0.0070 (8)
C11	0.0655 (12)	0.0490 (10)	0.0562 (11)	0.0092 (9)	0.0134 (9)	0.0007 (8)
C12	0.0563 (10)	0.0581 (11)	0.0420 (9)	0.0014 (8)	0.0058 (8)	−0.0014 (8)
C13	0.0856 (14)	0.0525 (11)	0.0487 (10)	0.0043 (10)	0.0128 (10)	0.0105 (8)
C14	0.0725 (12)	0.0439 (10)	0.0513 (10)	0.0070 (9)	0.0071 (9)	0.0020 (8)
C15	0.0748 (13)	0.0816 (15)	0.0580 (12)	0.0149 (12)	0.0158 (10)	−0.0087 (11)
C16	0.0625 (12)	0.0887 (16)	0.0584 (12)	−0.0087 (11)	−0.0020 (9)	0.0081 (11)
O3	0.0864 (10)	0.0724 (9)	0.0473 (8)	0.0108 (8)	0.0201 (7)	0.0009 (6)

Geometric parameters (Å, º) top

O1—C6	1.358 (2)	C8—C9	1.476 (2)
O1—C7	1.432 (2)	C9—C10	1.389 (2)
O2—C8	1.220 (2)	C9—C14	1.398 (3)
O4—N1	1.198 (2)	C10—C11	1.383 (3)
O5—N1	1.234 (2)	C10—H10	0.9300
N1—C1	1.460 (3)	C11—C12	1.381 (3)
C1—C2	1.376 (3)	C11—H11	0.9300
C1—C6	1.393 (2)	C12—O3	1.355 (2)
C2—C3	1.379 (3)	C12—C13	1.394 (3)
C2—H2	0.9300	C13—C14	1.366 (3)
C3—C4	1.377 (3)	C13—H13	0.9300
C3—H3	0.95 (2)	C14—H14	0.9300
C4—C5	1.376 (3)	C15—O3	1.433 (3)
C4—H4	0.9300	C15—H15A	0.9600
C5—C6	1.386 (3)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C7—C16	1.513 (3)	C16—H16A	0.9600
C7—C8	1.527 (3)	C16—H16B	0.9600
C7—H7	0.95 (2)	C16—H16C	0.9600

C6—O1—C7	117.85 (13)	C10—C9—C14	117.70 (16)
O4—N1—O5	123.4 (2)	C10—C9—C8	123.39 (16)
O4—N1—C1	119.49 (19)	C14—C9—C8	118.90 (16)
O5—N1—C1	117.1 (2)	C11—C10—C9	121.36 (17)
C2—C1—C6	122.16 (18)	C11—C10—H10	119.3
C2—C1—N1	117.83 (17)	C9—C10—H10	119.3
C6—C1—N1	120.00 (17)	C12—C11—C10	120.04 (17)
C1—C2—C3	119.60 (19)	C12—C11—H11	120.0
C1—C2—H2	120.2	C10—C11—H11	120.0
C3—C2—H2	120.2	O3—C12—C11	125.09 (17)
C4—C3—C2	119.0 (2)	O3—C12—C13	115.72 (16)
C4—C3—H3	122.0 (14)	C11—C12—C13	119.18 (17)
C2—C3—H3	119.0 (14)	C14—C13—C12	120.44 (18)
C5—C4—C3	121.4 (2)	C14—C13—H13	119.8
C5—C4—H4	119.3	C12—C13—H13	119.8
C3—C4—H4	119.3	C13—C14—C9	121.22 (17)
C4—C5—C6	120.60 (17)	C13—C14—H14	119.4
C4—C5—H5	119.7	C9—C14—H14	119.4
C6—C5—H5	119.7	O3—C15—H15A	109.5
O1—C6—C5	125.31 (15)	O3—C15—H15B	109.5
O1—C6—C1	117.36 (16)	H15A—C15—H15B	109.5
C5—C6—C1	117.29 (16)	O3—C15—H15C	109.5
O1—C7—C16	105.98 (15)	H15A—C15—H15C	109.5
O1—C7—C8	111.22 (15)	H15B—C15—H15C	109.5
C16—C7—C8	109.36 (15)	C7—C16—H16A	109.5
O1—C7—H7	109.4 (12)	C7—C16—H16B	109.5
C16—C7—H7	110.4 (12)	H16A—C16—H16B	109.5
C8—C7—H7	110.4 (12)	C7—C16—H16C	109.5
O2—C8—C9	121.82 (16)	H16A—C16—H16C	109.5
O2—C8—C7	118.95 (15)	H16B—C16—H16C	109.5
C9—C8—C7	119.14 (15)	C12—O3—C15	117.77 (16)

O4—N1—C1—C2	−131.6 (2)	C16—C7—C8—O2	92.3 (2)
O5—N1—C1—C2	47.3 (3)	O1—C7—C8—C9	159.03 (14)
O4—N1—C1—C6	49.4 (3)	C16—C7—C8—C9	−84.3 (2)
O5—N1—C1—C6	−131.7 (2)	O2—C8—C9—C10	164.16 (17)
C6—C1—C2—C3	−0.6 (3)	C7—C8—C9—C10	−19.4 (2)
N1—C1—C2—C3	−179.6 (2)	O2—C8—C9—C14	−14.6 (3)
C1—C2—C3—C4	1.5 (3)	C7—C8—C9—C14	161.91 (16)
C2—C3—C4—C5	−0.7 (3)	C14—C9—C10—C11	2.1 (3)
C3—C4—C5—C6	−1.0 (3)	C8—C9—C10—C11	−176.67 (17)
C7—O1—C6—C5	15.1 (3)	C9—C10—C11—C12	−1.6 (3)
C7—O1—C6—C1	−167.31 (16)	C10—C11—C12—O3	179.72 (18)
C4—C5—C6—O1	179.50 (18)	C10—C11—C12—C13	−0.4 (3)
C4—C5—C6—C1	1.9 (3)	O3—C12—C13—C14	−178.18 (18)
C2—C1—C6—O1	−178.91 (17)	C11—C12—C13—C14	1.9 (3)
N1—C1—C6—O1	0.0 (3)	C12—C13—C14—C9	−1.5 (3)
C2—C1—C6—C5	−1.1 (3)	C10—C9—C14—C13	−0.5 (3)
N1—C1—C6—C5	177.84 (17)	C8—C9—C14—C13	178.28 (17)
C6—O1—C7—C16	158.16 (16)	C11—C12—O3—C15	−0.6 (3)
C6—O1—C7—C8	−83.09 (19)	C13—C12—O3—C15	179.58 (18)
O1—C7—C8—O2	−24.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.95 (2)	2.51 (2)	3.363 (3)	149.6 (19)
C7—H7···O2ⁱⁱ	0.95 (2)	2.39 (2)	3.274 (2)	153.7 (17)

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

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1-(4-Methoxy­phenyl)-2-(2-nitro­phenoxy)­propan-1-one

Supporting information

Key indicators

checkCIF/PLATON results

1-(4-Methoxyphenyl)-2-(2-nitrophenoxy)propan-1-one