Literature DB >> 21582549

N-[(2-Hydr-oxy-5-methoxy-phen-yl)(3-nitro-phen-yl)meth-yl]acetamide.

M Nizammohideen, S Thenmozhi, A Subbiahpandi, N Panneer Selvam, P T Perumal.

Abstract

In the title compound, C(16)H(16)N(2)O(5), the meth-oxy group is disordered with site occupancies of 0.20 (3) and 0.80 (3). The dihedral angle between the two aromatic rings is 73.7 (2)°. The crystal structure is characterized by intermolecular N-H⋯O, O-H⋯O, C-H⋯O and C-H⋯π hydrogen bonds.

Entities: Chemical Disease Gene Species

Year: 2009 PMID： 21582549 PMCID： PMC2968863 DOI： 10.1107/S1600536809009726

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For N-substituted phenyl acetamides as intermediates in organic synthesis, see: Gowda et al. (2007 ▶); Ghosh et al. (2005 ▶). For a related structure, see: NizamMohideen et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H16N2O5 M = 316.31 Monoclinic, a = 15.3351 (3) Å b = 8.1327 (2) Å c = 14.5308 (3) Å β = 117.387 (1)° V = 1609.10 (6) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 293 K 0.32 × 0.28 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: none 23127 measured reflections 6121 independent reflections 3900 reflections with I > 2σ(I) R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.058 wR(F 2) = 0.196 S = 1.03 6121 reflections 216 parameters 1 restraint H-atom parameters constrained Δρmax = 0.41 e Å−3 Δρmin = −0.25 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009726/bt2901sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009726/bt2901Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₆H₁₆N₂O₅	F(000) = 664
M_r = 316.31	D_x = 1.306 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3900 reflections
a = 15.3351 (3) Å	θ = 2.5–25°
b = 8.1327 (2) Å	µ = 0.10 mm⁻¹
c = 14.5308 (3) Å	T = 293 K
β = 117.387 (1)°	Block, colourless
V = 1609.10 (6) Å³	0.32 × 0.28 × 0.25 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3900 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
graphite	θ_max = 33.2°, θ_min = 2.8°
ω and φ scans	h = −23→23
23127 measured reflections	k = −12→11
6121 independent reflections	l = −22→22

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.196	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1083P)² + 0.189P] where P = (F_o² + 2F_c²)/3
6121 reflections	(Δ/σ)_max = 0.002
216 parameters	Δρ_max = 0.41 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

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.

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1A	0.640 (2)	0.888 (2)	0.458 (2)	0.117 (3)	0.20 (3)
H1A1	0.6596	0.8863	0.4043	0.175*	0.20 (3)
H1A2	0.6970	0.8979	0.5243	0.175*	0.20 (3)
H1A3	0.5974	0.9805	0.4479	0.175*	0.20 (3)
C1B	0.6664 (8)	0.834 (2)	0.4528 (4)	0.117 (3)	0.80 (3)
H1B1	0.6854	0.7851	0.4044	0.175*	0.80 (3)
H1B2	0.7218	0.8351	0.5206	0.175*	0.80 (3)
H1B3	0.6444	0.9445	0.4316	0.175*	0.80 (3)
C2	0.50275 (11)	0.7283 (2)	0.36557 (11)	0.0484 (4)
C3	0.48701 (12)	0.7903 (2)	0.27035 (12)	0.0532 (4)
H3	0.5369	0.8465	0.2643	0.064*
C4	0.39705 (12)	0.7686 (2)	0.18441 (11)	0.0477 (4)
H4	0.3870	0.8102	0.1207	0.057*
C5	0.32155 (9)	0.68542 (15)	0.19185 (9)	0.0332 (3)
C6	0.33683 (9)	0.62281 (13)	0.28794 (8)	0.0278 (2)
C7	0.42728 (10)	0.64540 (17)	0.37363 (9)	0.0372 (3)
H7	0.4377	0.6044	0.4376	0.045*
C8	0.25554 (8)	0.53368 (14)	0.29997 (8)	0.0279 (2)
H8	0.2826	0.5052	0.3735	0.034*
C9	0.22779 (9)	0.37267 (14)	0.24099 (9)	0.0310 (2)
C10	0.28657 (13)	0.23670 (18)	0.28828 (12)	0.0516 (4)
H10	0.3393	0.2477	0.3541	0.062*
C11	0.26797 (18)	0.0857 (2)	0.23924 (16)	0.0808 (7)
H11	0.3072	−0.0042	0.2728	0.097*
C12	0.19121 (17)	0.0676 (2)	0.14040 (16)	0.0775 (7)
H12	0.1782	−0.0332	0.1064	0.093*
C13	0.13489 (12)	0.20355 (17)	0.09422 (12)	0.0478 (4)
C14	0.15003 (9)	0.35523 (14)	0.14216 (10)	0.0335 (2)
H14	0.1091	0.4436	0.1090	0.040*
C15	0.16393 (11)	0.7236 (2)	0.35184 (10)	0.0447 (3)
C16	0.07682 (16)	0.8327 (3)	0.32137 (16)	0.0799 (7)
H16A	0.0179	0.7684	0.2885	0.120*
H16B	0.0768	0.9151	0.2740	0.120*
H16C	0.0797	0.8848	0.3820	0.120*
N1	0.17154 (8)	0.64005 (14)	0.27656 (8)	0.0348 (2)
H1	0.1263	0.6493	0.2136	0.042*
N2	0.05722 (11)	0.18961 (17)	−0.01317 (11)	0.0577 (4)
O1	0.58945 (9)	0.7410 (2)	0.45516 (10)	0.0795 (5)
O2	0.23072 (7)	0.66466 (13)	0.11020 (7)	0.0423 (2)
H2	0.2299	0.7038	0.0578	0.063*
O3	0.05139 (15)	0.06269 (19)	−0.06005 (12)	0.1014 (7)
O4	0.00217 (11)	0.30376 (18)	−0.05160 (11)	0.0816 (5)
O5	0.22599 (10)	0.7079 (2)	0.44251 (9)	0.0746 (5)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.050 (3)	0.233 (7)	0.0560 (14)	−0.069 (5)	0.0140 (19)	0.011 (3)
C1B	0.050 (3)	0.233 (7)	0.0560 (14)	−0.069 (5)	0.0140 (19)	0.011 (3)
C2	0.0342 (7)	0.0719 (10)	0.0316 (6)	−0.0132 (6)	0.0086 (6)	0.0049 (6)
C3	0.0426 (8)	0.0758 (11)	0.0417 (8)	−0.0160 (7)	0.0199 (7)	0.0096 (7)
C4	0.0465 (8)	0.0653 (9)	0.0314 (6)	−0.0103 (7)	0.0180 (6)	0.0115 (6)
C5	0.0347 (6)	0.0399 (6)	0.0226 (5)	−0.0013 (5)	0.0111 (5)	0.0041 (4)
C6	0.0304 (5)	0.0314 (5)	0.0214 (4)	0.0003 (4)	0.0118 (4)	0.0018 (4)
C7	0.0344 (6)	0.0493 (7)	0.0238 (5)	−0.0044 (5)	0.0100 (5)	0.0049 (5)
C8	0.0300 (5)	0.0332 (5)	0.0188 (4)	−0.0004 (4)	0.0098 (4)	0.0001 (3)
C9	0.0334 (6)	0.0320 (5)	0.0252 (5)	−0.0019 (4)	0.0116 (5)	0.0010 (4)
C10	0.0575 (9)	0.0393 (7)	0.0350 (7)	0.0069 (6)	0.0017 (7)	0.0016 (5)
C11	0.0947 (16)	0.0388 (8)	0.0589 (11)	0.0212 (9)	−0.0076 (11)	−0.0013 (7)
C12	0.0909 (15)	0.0358 (7)	0.0598 (11)	0.0108 (8)	−0.0046 (10)	−0.0117 (7)
C13	0.0477 (8)	0.0378 (6)	0.0380 (7)	0.0005 (6)	0.0026 (6)	−0.0079 (5)
C14	0.0328 (6)	0.0327 (5)	0.0294 (5)	0.0003 (4)	0.0095 (5)	−0.0018 (4)
C15	0.0397 (7)	0.0641 (9)	0.0296 (6)	0.0056 (6)	0.0154 (6)	−0.0126 (6)
C16	0.0686 (13)	0.1103 (17)	0.0559 (11)	0.0371 (12)	0.0245 (10)	−0.0197 (11)
N1	0.0314 (5)	0.0479 (6)	0.0216 (4)	0.0042 (4)	0.0092 (4)	−0.0058 (4)
N2	0.0559 (8)	0.0492 (7)	0.0434 (7)	0.0002 (6)	0.0016 (6)	−0.0162 (6)
O1	0.0415 (7)	0.1398 (13)	0.0397 (6)	−0.0371 (8)	0.0038 (5)	0.0145 (7)
O2	0.0397 (5)	0.0583 (6)	0.0221 (4)	−0.0068 (4)	0.0085 (4)	0.0098 (4)
O3	0.1210 (15)	0.0656 (9)	0.0623 (9)	0.0099 (9)	−0.0052 (9)	−0.0328 (7)
O4	0.0698 (9)	0.0699 (8)	0.0517 (7)	0.0233 (7)	−0.0179 (7)	−0.0195 (6)
O5	0.0692 (9)	0.1152 (11)	0.0278 (5)	0.0295 (8)	0.0124 (6)	−0.0204 (6)

C1A—O1	1.416 (4)	C9—C14	1.3888 (17)
C1A—H1A1	0.9600	C9—C10	1.3920 (18)
C1A—H1A2	0.9600	C10—C11	1.382 (2)
C1A—H1A3	0.9600	C10—H10	0.9300
C1B—O1	1.416 (4)	C11—C12	1.384 (3)
C1B—H1B1	0.9600	C11—H11	0.9300
C1B—H1B2	0.9600	C12—C13	1.373 (2)
C1B—H1B3	0.9600	C12—H12	0.9300
C2—O1	1.3714 (18)	C13—C14	1.3827 (18)
C2—C3	1.386 (2)	C13—N2	1.4685 (19)
C2—C7	1.390 (2)	C14—H14	0.9300
C3—C4	1.382 (2)	C15—O5	1.2264 (18)
C3—H3	0.9300	C15—O5	1.2264 (18)
C4—C5	1.3872 (18)	C15—N1	1.3375 (15)
C4—H4	0.9300	C15—C16	1.491 (2)
C5—O2	1.3623 (15)	C16—H16A	0.9600
C5—C6	1.4010 (15)	C16—H16B	0.9600
C6—C7	1.3854 (17)	C16—H16C	0.9600
C6—C8	1.5199 (16)	N1—H1	0.8600
C7—H7	0.9300	N2—O4	1.2052 (19)
C8—N1	1.4561 (15)	N2—O3	1.2172 (18)
C8—C9	1.5149 (16)	O2—H2	0.8200
C8—H8	0.9800

O1—C1A—H1A1	109.5	C11—C10—C9	121.21 (14)
O1—C1A—H1A2	109.5	C11—C10—H10	119.4
O1—C1A—H1A3	109.5	C9—C10—H10	119.4
O1—C1B—H1B1	109.5	C10—C11—C12	120.34 (15)
O1—C1B—H1B2	109.5	C10—C11—H11	119.8
H1B1—C1B—H1B2	109.5	C12—C11—H11	119.8
O1—C1B—H1B3	109.5	C13—C12—C11	117.69 (14)
H1B1—C1B—H1B3	109.5	C13—C12—H12	121.2
H1B2—C1B—H1B3	109.5	C11—C12—H12	121.2
O1—C2—C3	124.59 (13)	C12—C13—C14	123.38 (14)
O1—C2—C7	115.97 (12)	C12—C13—N2	118.51 (13)
C3—C2—C7	119.43 (13)	C14—C13—N2	118.06 (12)
C4—C3—C2	119.91 (13)	C13—C14—C9	118.51 (12)
C4—C3—H3	120.0	C13—C14—H14	120.7
C2—C3—H3	120.0	C9—C14—H14	120.7
C3—C4—C5	120.94 (12)	O5—C15—N1	120.63 (13)
C3—C4—H4	119.5	O5—C15—N1	120.63 (13)
C5—C4—H4	119.5	O5—C15—C16	121.81 (13)
O2—C5—C4	123.24 (11)	O5—C15—C16	121.81 (13)
O2—C5—C6	117.27 (11)	N1—C15—C16	117.56 (13)
C4—C5—C6	119.46 (12)	C15—C16—H16A	109.5
C7—C6—C5	119.13 (11)	C15—C16—H16B	109.5
C7—C6—C8	119.67 (9)	H16A—C16—H16B	109.5
C5—C6—C8	121.19 (10)	C15—C16—H16C	109.5
C6—C7—C2	121.12 (11)	H16A—C16—H16C	109.5
C6—C7—H7	119.4	H16B—C16—H16C	109.5
C2—C7—H7	119.4	C15—N1—C8	120.75 (11)
N1—C8—C9	113.16 (10)	C15—N1—H1	119.6
N1—C8—C6	111.96 (9)	C8—N1—H1	119.6
C9—C8—C6	112.27 (9)	O4—N2—O3	122.58 (15)
N1—C8—H8	106.3	O4—N2—C13	119.06 (12)
C9—C8—H8	106.3	O3—N2—C13	118.36 (14)
C6—C8—H8	106.3	C2—O1—C1B	118.2 (3)
C14—C9—C10	118.84 (11)	C2—O1—C1A	111.8 (10)
C14—C9—C8	123.88 (10)	C5—O2—H2	109.5
C10—C9—C8	117.24 (11)

O1—C2—C3—C4	179.06 (19)	C9—C10—C11—C12	1.5 (4)
C7—C2—C3—C4	−0.4 (3)	C10—C11—C12—C13	−0.4 (4)
C2—C3—C4—C5	0.2 (3)	C11—C12—C13—C14	−1.3 (4)
C3—C4—C5—O2	178.11 (15)	C11—C12—C13—N2	176.0 (2)
C3—C4—C5—C6	0.1 (2)	C12—C13—C14—C9	1.9 (3)
O2—C5—C6—C7	−178.18 (11)	N2—C13—C14—C9	−175.45 (14)
O2—C5—C6—C8	0.70 (17)	C10—C9—C14—C13	−0.8 (2)
C4—C5—C6—C8	178.87 (12)	C8—C9—C14—C13	176.87 (13)
C5—C6—C7—C2	−0.3 (2)	O5—C15—N1—C8	−2.4 (2)
C8—C6—C7—C2	−179.14 (13)	O5—C15—N1—C8	−2.4 (2)
O1—C2—C7—C6	−179.05 (15)	C16—C15—N1—C8	178.72 (17)
C3—C2—C7—C6	0.5 (2)	C9—C8—N1—C15	138.63 (13)
C7—C6—C8—N1	116.41 (12)	C6—C8—N1—C15	−93.27 (14)
C5—C6—C8—N1	−62.46 (13)	C12—C13—N2—O4	173.9 (2)
C7—C6—C8—C9	−115.02 (12)	C14—C13—N2—O4	−8.6 (3)
C5—C6—C8—C9	66.11 (14)	C12—C13—N2—O3	−6.4 (3)
N1—C8—C9—C14	32.10 (15)	C14—C13—N2—O3	171.07 (19)
C6—C8—C9—C14	−95.83 (14)	C3—C2—O1—C1B	4.8 (10)
N1—C8—C9—C10	−150.24 (13)	C7—C2—O1—C1B	−175.7 (9)
C6—C8—C9—C10	81.83 (14)	C3—C2—O1—C1A	32.3 (18)
C14—C9—C10—C11	−0.8 (3)	C7—C2—O1—C1A	−148.2 (18)
C8—C9—C10—C11	−178.63 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O5ⁱ	0.82	1.80	2.617 (2)	179
N1—H1···O4ⁱⁱ	0.86	2.30	3.159 (2)	174
C10—H10···O1ⁱⁱⁱ	0.93	2.47	3.320 (2)	152
C12—H12···O2^iv	0.93	2.58	3.397 (2)	147
C14—H14···O4ⁱⁱ	0.93	2.55	3.470 (2)	169
C8—H8···O5	0.98	2.30	2.714 (2)	105
C11—H11···Cg1^iv	0.93	2.83	3.680 (2)	153
C1B—H1B1···Cg2^v	0.96	2.61	3.531 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O5ⁱ	0.82	1.80	2.617 (2)	179
N1—H1⋯O4ⁱⁱ	0.86	2.30	3.159 (2)	174
C10—H10⋯O1ⁱⁱⁱ	0.93	2.47	3.320 (2)	152
C12—H12⋯O2^iv	0.93	2.58	3.397 (2)	147
C14—H14⋯O4ⁱⁱ	0.93	2.55	3.470 (2)	169
C8—H8⋯O5	0.98	2.30	2.714 (2)	105
C11—H11⋯Cg1^iv	0.93	2.83	3.680 (2)	153
C1B—H1B1⋯Cg2^v	0.96	2.61	3.531 (2)	160

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 and Cg2 are the centroids of the C2-C7 and C9-C14 rings, respectively.

3 in total

N-[(2-Hydr-oxy-5-methoxy-phen-yl)(3-nitro-phen-yl)meth-yl]acetamide.

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

2. N-[(2-Hydr-oxy-1-naphthyl)(3-nitro-phenyl)meth-yl]acetamide.

3. Structure validation in chemical crystallography.