N-Benzyl-2-(2-bromo-phen-yl)-2-(2-nitro-phen-oxy)acetamide.

The title compound, C(21)H(17)BrN(2)O(4), a 2-phen-oxy-2-phenyl-acetamide derivative, exhibits a stereogenic center but crystallizes as a racemate as indicated by the centrosymmetric space group. In the mol-ecular structure, the nitro-substituted benzene ring is coplanar [dihedral angle = 12.9 (1)°] with the plane formed by H-N-C(=O)-C=O due to intra-molecular N-H⋯O hydrogen-bond inter-actions.

Related literature

For the synthesis and biological activity of 2-phen­oxy-2-phenyl-acetamides, see: Dorsch et al. (2002 ▶); Wang et al. (2010 ▶); Lau et al. (2003 ▶). For additional synthetic procedures, see: Dai & Li (2007 ▶).

Experimental

Crystal data

C21H17BrN2O4

M = 441.28

Triclinic,

a = 7.5818 (5) Å

b = 10.4650 (7) Å

c = 13.1095 (10) Å

α = 73.939 (6)°

β = 82.878 (6)°

γ = 74.447 (6)°

V = 961.56 (12) Å3

Z = 2

Cu Kα radiation

μ = 3.17 mm−1

T = 293 K

0.38 × 0.26 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.427, T max = 0.565

7135 measured reflections

3363 independent reflections

2522 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.03

3363 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.39 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810014996/im2196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014996/im2196Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H17BrN2O4	Z = 2
Mr = 441.28	F(000) = 448
Triclinic, P1	Dx = 1.524 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.5818 (5) Å	Cell parameters from 3052 reflections
b = 10.4650 (7) Å	θ = 3.5–66.9°
c = 13.1095 (10) Å	µ = 3.17 mm−1
α = 73.939 (6)°	T = 293 K
β = 82.878 (6)°	Block, colorless
γ = 74.447 (6)°	0.38 × 0.26 × 0.18 mm
V = 961.56 (12) Å3

Oxford Diffraction Xcalibur Atlas Gemini ultra diffractometer	3363 independent reflections
Radiation source: fine-focus sealed tube	2522 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 10.3592 pixels mm-1	θmax = 66.6°, θmin = 3.5°
ω scans	h = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→12
Tmin = 0.427, Tmax = 0.565	l = −15→15
7135 measured reflections

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0523P)2 + 0.350P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3363 reflections	Δρmax = 0.37 e Å−3
254 parameters	Δρmin = −0.39 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0258 (10)

Experimental. (CrysAlis Pro; Oxford Diffraction, 2009) Version 1.171.33.53 (release 17-11-2009 CrysAlis171 .NET) (compiled Nov 17 2009,16:58:22) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

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	Uiso*/Ueq
Br27	0.67572 (5)	0.56595 (4)	0.87665 (3)	0.0848 (2)
O2	0.3651 (3)	0.99683 (19)	0.82814 (14)	0.0599 (5)
O24	0.6787 (3)	0.8846 (3)	0.63093 (18)	0.0856 (7)
O25	0.2519 (5)	1.2538 (2)	0.8109 (2)	0.1010 (9)
O26	0.0566 (5)	1.3176 (3)	0.9264 (3)	0.1318 (13)
N22	0.5004 (4)	1.0913 (3)	0.64616 (19)	0.0712 (7)
H22	0.4153	1.1318	0.6846	0.085*
N23	0.1698 (4)	1.2288 (3)	0.8964 (2)	0.0653 (7)
C1	0.6438 (6)	1.3641 (4)	0.5979 (3)	0.0878 (11)
H1	0.5190	1.4028	0.6064	0.105*
C2	0.7724 (10)	1.4280 (5)	0.6178 (3)	0.1174 (18)
H2	0.7341	1.5090	0.6395	0.141*
C3	0.9541 (11)	1.3690 (8)	0.6046 (4)	0.126 (2)
H3	1.0401	1.4101	0.6182	0.152*
C4	1.0118 (7)	1.2529 (7)	0.5724 (4)	0.1164 (18)
H4	1.1365	1.2150	0.5628	0.140*
C5	0.8863 (5)	1.1907 (4)	0.5537 (3)	0.0829 (10)
H5	0.9267	1.1098	0.5320	0.099*
C6	0.7016 (4)	1.2457 (4)	0.5664 (2)	0.0629 (8)
C7	0.5676 (6)	1.1746 (5)	0.5464 (3)	0.0911 (13)
H7B	0.4646	1.2424	0.5108	0.109*
H7A	0.6259	1.1159	0.4998	0.109*
C8	0.5655 (4)	0.9562 (4)	0.6794 (2)	0.0615 (8)
C9	0.4855 (4)	0.8876 (3)	0.7880 (2)	0.0515 (6)
H9	0.5849	0.8396	0.8363	0.062*
C10	0.3835 (4)	0.7874 (3)	0.7772 (2)	0.0477 (6)
C11	0.4463 (4)	0.6461 (3)	0.8127 (2)	0.0577 (7)
C12	0.3448 (5)	0.5585 (3)	0.8030 (3)	0.0745 (9)
H12	0.3896	0.4642	0.8271	0.089*
C13	0.1799 (5)	0.6103 (4)	0.7584 (3)	0.0750 (9)
H13	0.1110	0.5511	0.7532	0.090*
C14	0.1141 (4)	0.7491 (4)	0.7209 (2)	0.0673 (8)
H14	0.0017	0.7842	0.6895	0.081*
C15	0.2163 (4)	0.8368 (3)	0.7301 (2)	0.0558 (7)
H15	0.1716	0.9309	0.7040	0.067*
C16	0.3115 (4)	0.9775 (3)	0.93255 (19)	0.0460 (6)
C17	0.3463 (4)	0.8503 (3)	1.0060 (2)	0.0544 (7)
H17	0.4134	0.7728	0.9846	0.065*
C18	0.2821 (4)	0.8388 (3)	1.1098 (2)	0.0631 (8)
H18	0.3077	0.7534	1.1583	0.076*
C19	0.1805 (4)	0.9514 (4)	1.1434 (2)	0.0698 (9)
H19	0.1373	0.9420	1.2140	0.084*
C20	0.1435 (4)	1.0772 (3)	1.0723 (2)	0.0628 (8)
H20	0.0739	1.1537	1.0943	0.075*
C21	0.2096 (4)	1.0908 (3)	0.9674 (2)	0.0488 (6)

	U11	U22	U33	U12	U13	U23
Br27	0.0661 (3)	0.0668 (3)	0.1161 (4)	0.00496 (17)	−0.0286 (2)	−0.0247 (2)
O2	0.0875 (14)	0.0447 (10)	0.0454 (10)	−0.0160 (10)	0.0037 (9)	−0.0113 (8)
O24	0.0676 (14)	0.124 (2)	0.0680 (14)	−0.0247 (14)	0.0139 (12)	−0.0354 (14)
O25	0.165 (3)	0.0495 (13)	0.0740 (16)	−0.0125 (15)	−0.0038 (18)	−0.0060 (12)
O26	0.135 (3)	0.0565 (16)	0.171 (3)	0.0045 (17)	0.036 (2)	−0.0219 (18)
N22	0.0792 (18)	0.085 (2)	0.0506 (14)	−0.0405 (16)	0.0013 (13)	−0.0016 (13)
N23	0.0701 (16)	0.0466 (14)	0.084 (2)	−0.0138 (13)	−0.0136 (14)	−0.0209 (13)
C1	0.103 (3)	0.087 (3)	0.062 (2)	−0.022 (2)	0.0102 (19)	−0.0068 (19)
C2	0.201 (6)	0.094 (3)	0.068 (3)	−0.065 (4)	0.000 (3)	−0.015 (2)
C3	0.175 (6)	0.149 (5)	0.083 (3)	−0.113 (5)	−0.031 (4)	0.009 (3)
C4	0.085 (3)	0.156 (5)	0.099 (3)	−0.057 (3)	−0.020 (2)	0.014 (3)
C5	0.081 (2)	0.089 (3)	0.069 (2)	−0.025 (2)	−0.0016 (18)	−0.0021 (18)
C6	0.071 (2)	0.078 (2)	0.0367 (14)	−0.0313 (17)	−0.0043 (13)	0.0037 (14)
C7	0.104 (3)	0.126 (3)	0.0500 (18)	−0.070 (3)	−0.0088 (18)	0.0084 (19)
C8	0.0524 (17)	0.088 (2)	0.0523 (17)	−0.0299 (17)	−0.0051 (14)	−0.0172 (16)
C9	0.0577 (16)	0.0545 (15)	0.0455 (14)	−0.0160 (13)	−0.0042 (12)	−0.0152 (12)
C10	0.0467 (14)	0.0546 (15)	0.0455 (14)	−0.0130 (12)	0.0004 (11)	−0.0192 (12)
C11	0.0501 (15)	0.0574 (17)	0.0684 (18)	−0.0065 (13)	−0.0058 (13)	−0.0256 (14)
C12	0.077 (2)	0.0560 (18)	0.100 (3)	−0.0164 (16)	−0.0095 (19)	−0.0330 (17)
C13	0.075 (2)	0.079 (2)	0.088 (2)	−0.0344 (19)	−0.0033 (18)	−0.0341 (19)
C14	0.0490 (16)	0.098 (3)	0.0607 (18)	−0.0223 (17)	−0.0044 (14)	−0.0242 (17)
C15	0.0513 (15)	0.0632 (17)	0.0507 (15)	−0.0112 (14)	−0.0016 (12)	−0.0142 (13)
C16	0.0512 (14)	0.0500 (14)	0.0443 (14)	−0.0208 (12)	−0.0049 (11)	−0.0148 (11)
C17	0.0654 (17)	0.0504 (15)	0.0479 (15)	−0.0143 (13)	−0.0077 (13)	−0.0114 (12)
C18	0.0674 (19)	0.071 (2)	0.0466 (16)	−0.0188 (16)	−0.0079 (14)	−0.0045 (14)
C19	0.0681 (19)	0.094 (3)	0.0481 (16)	−0.0191 (18)	−0.0003 (14)	−0.0220 (17)
C20	0.0556 (17)	0.075 (2)	0.0663 (19)	−0.0107 (15)	−0.0044 (14)	−0.0361 (16)
C21	0.0486 (14)	0.0482 (14)	0.0561 (16)	−0.0161 (12)	−0.0107 (12)	−0.0165 (12)

Br27—C11	1.903 (3)	C8—C9	1.538 (4)
O2—C16	1.354 (3)	C9—C10	1.504 (4)
O2—C9	1.439 (3)	C9—H9	0.9800
O24—C8	1.218 (4)	C10—C15	1.386 (4)
O25—N23	1.209 (4)	C10—C11	1.388 (4)
O26—N23	1.203 (4)	C11—C12	1.384 (4)
N22—C8	1.331 (4)	C12—C13	1.357 (5)
N22—C7	1.473 (4)	C12—H12	0.9300
N22—H22	0.8600	C13—C14	1.370 (5)
N23—C21	1.461 (4)	C13—H13	0.9300
C1—C6	1.358 (5)	C14—C15	1.387 (4)
C1—C2	1.406 (7)	C14—H14	0.9300
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.361 (8)	C16—C17	1.391 (4)
C2—H2	0.9300	C16—C21	1.391 (4)
C3—C4	1.341 (8)	C17—C18	1.371 (4)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.367 (6)	C18—C19	1.375 (5)
C4—H4	0.9300	C18—H18	0.9300
C5—C6	1.372 (5)	C19—C20	1.367 (5)
C5—H5	0.9300	C19—H19	0.9300
C6—C7	1.494 (5)	C20—C21	1.386 (4)
C7—H7B	0.9700	C20—H20	0.9300
C7—H7A	0.9700
C16—O2—C9	121.1 (2)	C10—C9—H9	109.5
C8—N22—C7	122.8 (3)	C8—C9—H9	109.5
C8—N22—H22	118.6	C15—C10—C11	117.2 (3)
C7—N22—H22	118.6	C15—C10—C9	119.1 (3)
O26—N23—O25	120.9 (3)	C11—C10—C9	123.7 (2)
O26—N23—C21	118.1 (3)	C12—C11—C10	121.3 (3)
O25—N23—C21	120.9 (3)	C12—C11—Br27	117.6 (2)
C6—C1—C2	120.0 (4)	C10—C11—Br27	121.0 (2)
C6—C1—H1	120.0	C13—C12—C11	120.1 (3)
C2—C1—H1	120.0	C13—C12—H12	120.0
C3—C2—C1	118.7 (5)	C11—C12—H12	120.0
C3—C2—H2	120.7	C12—C13—C14	120.4 (3)
C1—C2—H2	120.7	C12—C13—H13	119.8
C4—C3—C2	121.5 (5)	C14—C13—H13	119.8
C4—C3—H3	119.3	C13—C14—C15	119.5 (3)
C2—C3—H3	119.3	C13—C14—H14	120.2
C3—C4—C5	119.6 (5)	C15—C14—H14	120.2
C3—C4—H4	120.2	C10—C15—C14	121.5 (3)
C5—C4—H4	120.2	C10—C15—H15	119.3
C4—C5—C6	121.1 (5)	C14—C15—H15	119.3
C4—C5—H5	119.4	O2—C16—C17	123.9 (2)
C6—C5—H5	119.4	O2—C16—C21	117.9 (2)
C1—C6—C5	119.1 (4)	C17—C16—C21	118.2 (2)
C1—C6—C7	121.0 (4)	C18—C17—C16	120.2 (3)
C5—C6—C7	119.9 (4)	C18—C17—H17	119.9
N22—C7—C6	111.5 (3)	C16—C17—H17	119.9
N22—C7—H7B	109.3	C17—C18—C19	121.2 (3)
C6—C7—H7B	109.3	C17—C18—H18	119.4
N22—C7—H7A	109.3	C19—C18—H18	119.4
C6—C7—H7A	109.3	C20—C19—C18	119.5 (3)
H7B—C7—H7A	108.0	C20—C19—H19	120.2
O24—C8—N22	125.8 (3)	C18—C19—H19	120.2
O24—C8—C9	118.7 (3)	C19—C20—C21	120.0 (3)
N22—C8—C9	115.5 (3)	C19—C20—H20	120.0
O2—C9—C10	111.1 (2)	C21—C20—H20	120.0
O2—C9—C8	106.1 (2)	C20—C21—C16	120.9 (3)
C10—C9—C8	111.0 (2)	C20—C21—N23	117.2 (3)
O2—C9—H9	109.5	C16—C21—N23	121.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N22—H22···O2	0.86	2.08	2.521 (3)	111
N22—H22···O25	0.86	2.39	3.227 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N22—H22⋯O2	0.86	2.08	2.521 (3)	111
N22—H22⋯O25	0.86	2.39	3.227 (4)	164