N-Éthyl-N-[2-(3-phénylisoxazol-5-ylméthylamino)phényl]benzylacétamide

In the structure of the title compound, C₂₇H₂₇N₃O₂, the methylamino-phenylisoxazole fragment and the N-ethyl­benzylacetamide arm are attached to the phenyl ring and are oriented in opposite directions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.072
• wR factor = 0.185
• Data-to-parameter ratio = 14.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: KappaCCD Reference Manual (Nonius, 1998); cell refinement: DENZO–SMN; data reduction: DENZO–SMN (Otwinowski & Minor, 1997) and maXus (Mackay et al., 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

N-Éthyl-N-[2-(3-phénylisoxazol-5-ylméthylamino)phényl]benzylacétamide

Crystal data

C27H27N3O2	Z = 2
Mr = 425.52	F(000) = 452
Triclinic, P1	Dx = 1.231 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.825 (1) Å	Cell parameters from 7208 reflections
b = 10.999 (1) Å	θ = 2.9–25.3°
c = 12.095 (1) Å	µ = 0.08 mm^−1
α = 91.56 (1)°	T = 293 K
β = 109.22 (1)°	Cube, colourless
γ = 109.37 (1)°	0.40 × 0.35 × 0.35 mm
V = 1150.6 (2) Å^3

Data collection

Nonius KappaCCD diffractometer	3234 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 25.3°, θmin = 2.9°
φ scans	h = 0→11
7208 measured reflections	k = −13→13
4048 independent reflections	l = −14→14

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.185	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0673P)^2 + 0.3922P] where P = (Fo^2 + 2Fc^2)/3
4048 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.45 e Å^−3
0 restraints	Δρmin = −0.26 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
O11	−0.55000 (18)	0.00136 (16)	−0.16947 (15)	0.0762 (5)
O23	0.14554 (17)	0.22760 (16)	0.40361 (15)	0.0735 (5)
N7	−0.29506 (18)	0.08889 (16)	−0.06184 (14)	0.0518 (4)
N20	−0.17828 (19)	0.21900 (17)	0.16974 (14)	0.0546 (4)
H20	−0.2728	0.1385	0.1385	0.065*
N24	0.2166 (2)	0.1347 (2)	0.43665 (19)	0.0737 (6)
C1	−0.1526 (2)	0.19972 (19)	−0.02051 (18)	0.0508 (5)
C2	−0.0749 (3)	0.2447 (2)	−0.0964 (2)	0.0690 (6)
H2	−0.1211	0.2053	−0.1782	0.083*
C3	0.0645 (3)	0.3464 (3)	−0.0566 (3)	0.0816 (8)
H3	0.1184	0.3778	−0.1094	0.098*
C4	0.1283 (3)	0.4002 (3)	0.0591 (3)	0.0768 (7)
H4	0.2274	0.4693	0.0884	0.092*
C5	0.0528 (2)	0.3578 (2)	0.1368 (2)	0.0640 (6)
H5	0.1014	0.3975	0.2184	0.077*
C6	−0.0920 (2)	0.25758 (19)	0.09785 (17)	0.0487 (5)
C8	−0.2822 (3)	−0.0389 (2)	−0.0441 (2)	0.0681 (6)
H8A	−0.2163	−0.0338	0.0360	0.082*
H8B	−0.3834	−0.1017	−0.0580	0.082*
C9	−0.2177 (4)	−0.0854 (3)	−0.1262 (3)	0.1003 (10)
H9A	−0.2125	−0.1692	−0.1108	0.120*
H9B	−0.1158	−0.0243	−0.1129	0.120*
H9C	−0.2828	−0.0922	−0.2069	0.120*
C10	−0.4311 (2)	0.0987 (2)	−0.12721 (18)	0.0565 (5)
C12	−0.4284 (3)	0.2332 (2)	−0.1447 (2)	0.0746 (7)
H12A	−0.3518	0.2707	−0.1792	0.089*
H12B	−0.3977	0.2815	−0.0678	0.089*
C13	−0.5747 (3)	0.2415 (3)	−0.2222 (3)	0.0982 (10)
H13A	−0.6077	0.1903	−0.2981	0.118*
H13B	−0.6506	0.2071	−0.1862	0.118*
C14	−0.5665 (3)	0.3777 (3)	−0.2396 (2)	0.0715 (7)
C15	−0.6035 (3)	0.4479 (4)	−0.1687 (3)	0.0943 (9)
H15	−0.6288	0.4098	−0.1042	0.113*
C16	−0.6013 (4)	0.5707 (4)	−0.1836 (3)	0.1076 (11)
H16	−0.6375	0.6107	−0.1332	0.129*
C17	−0.5572 (4)	0.6297 (3)	−0.2670 (3)	0.0941 (9)
H17	−0.5572	0.7166	−0.2736	0.113*
C18	−0.5134 (4)	0.5650 (4)	−0.3387 (3)	0.1083 (11)
H18	−0.4765	0.6083	−0.3967	0.130*
C19	−0.5196 (4)	0.4392 (4)	−0.3260 (3)	0.1013 (11)
H19	−0.4923	0.3920	−0.3779	0.122*
C21	−0.1054 (3)	0.2411 (2)	0.29777 (19)	0.0635 (6)
H21A	−0.1848	0.2194	0.3314	0.076*
H21B	−0.0437	0.3322	0.3212	0.076*
C22	−0.0054 (2)	0.1636 (2)	0.34253 (17)	0.0551 (5)
C25	0.1070 (2)	0.0214 (2)	0.39363 (16)	0.0557 (5)
C26	−0.0356 (2)	0.0358 (2)	0.33372 (19)	0.0622 (6)
H26	−0.1391	−0.0241	0.2921	0.075*
C27	0.1382 (2)	−0.0998 (2)	0.40833 (18)	0.0600 (6)
C28	0.2871 (3)	−0.1006 (3)	0.4452 (3)	0.0876 (8)
H28	0.3717	−0.0187	0.4643	0.105*
C29	0.3139 (4)	−0.2151 (4)	0.4571 (3)	0.1009 (10)
H29	0.4185	−0.2125	0.4819	0.121*
C30	0.1952 (4)	−0.3314 (3)	0.4316 (3)	0.0899 (8)
H30	0.2158	−0.4108	0.4392	0.108*
C31	0.0467 (3)	−0.3330 (3)	0.3948 (2)	0.0797 (7)
H31	−0.0400	−0.4133	0.3771	0.096*
C32	0.0183 (3)	−0.2189 (2)	0.38347 (19)	0.0658 (6)
H32	−0.0863	−0.2219	0.3582	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0567 (9)	0.0624 (11)	0.0797 (11)	−0.0016 (7)	0.0113 (8)	0.0001 (8)
O23	0.0548 (9)	0.0652 (11)	0.0788 (11)	0.0124 (7)	0.0070 (7)	0.0004 (8)
N7	0.0517 (9)	0.0423 (10)	0.0557 (9)	0.0105 (7)	0.0189 (7)	0.0050 (7)
N20	0.0497 (9)	0.0562 (11)	0.0533 (10)	0.0163 (7)	0.0163 (7)	0.0020 (7)
N24	0.0527 (10)	0.0706 (14)	0.0797 (13)	0.0174 (9)	0.0066 (9)	0.0052 (10)
C1	0.0458 (10)	0.0457 (11)	0.0579 (11)	0.0132 (8)	0.0184 (8)	0.0083 (8)
C2	0.0614 (13)	0.0770 (16)	0.0647 (14)	0.0129 (11)	0.0296 (11)	0.0141 (11)
C3	0.0639 (14)	0.0862 (19)	0.0889 (19)	0.0093 (13)	0.0374 (13)	0.0240 (14)
C4	0.0499 (12)	0.0623 (15)	0.104 (2)	0.0042 (10)	0.0252 (13)	0.0186 (13)
C5	0.0509 (11)	0.0519 (13)	0.0737 (14)	0.0116 (9)	0.0108 (10)	0.0015 (10)
C6	0.0454 (10)	0.0420 (11)	0.0588 (11)	0.0183 (8)	0.0161 (8)	0.0082 (8)
C8	0.0737 (14)	0.0501 (14)	0.0759 (15)	0.0179 (10)	0.0256 (12)	0.0074 (10)
C9	0.109 (2)	0.072 (2)	0.132 (3)	0.0370 (16)	0.056 (2)	−0.0037 (17)
C10	0.0516 (11)	0.0531 (13)	0.0524 (11)	0.0086 (9)	0.0141 (9)	0.0022 (8)
C12	0.0616 (13)	0.0585 (15)	0.0802 (16)	0.0169 (11)	0.0015 (11)	0.0048 (11)
C13	0.0744 (17)	0.080 (2)	0.101 (2)	0.0206 (14)	−0.0090 (15)	0.0065 (15)
C14	0.0545 (12)	0.0689 (16)	0.0686 (15)	0.0227 (11)	−0.0057 (10)	0.0023 (11)
C15	0.0780 (18)	0.114 (3)	0.109 (2)	0.0443 (17)	0.0444 (16)	0.0297 (18)
C16	0.110 (3)	0.126 (3)	0.110 (3)	0.072 (2)	0.041 (2)	0.009 (2)
C17	0.090 (2)	0.079 (2)	0.105 (2)	0.0439 (16)	0.0105 (17)	0.0110 (17)
C18	0.131 (3)	0.131 (3)	0.094 (2)	0.076 (2)	0.047 (2)	0.054 (2)
C19	0.144 (3)	0.124 (3)	0.0641 (16)	0.091 (2)	0.0293 (17)	0.0188 (16)
C21	0.0663 (13)	0.0676 (15)	0.0559 (12)	0.0257 (11)	0.0204 (10)	−0.0031 (10)
C22	0.0501 (11)	0.0647 (14)	0.0441 (10)	0.0158 (9)	0.0147 (8)	−0.0025 (8)
C25	0.0489 (11)	0.0665 (14)	0.0435 (10)	0.0150 (9)	0.0127 (8)	0.0024 (9)
C26	0.0467 (11)	0.0652 (15)	0.0614 (13)	0.0141 (9)	0.0095 (9)	−0.0007 (10)
C27	0.0554 (12)	0.0721 (15)	0.0459 (11)	0.0222 (10)	0.0111 (9)	0.0035 (9)
C28	0.0550 (14)	0.083 (2)	0.110 (2)	0.0244 (13)	0.0111 (13)	0.0091 (15)
C29	0.0770 (19)	0.101 (3)	0.120 (3)	0.0481 (18)	0.0144 (17)	0.0106 (18)
C30	0.103 (2)	0.083 (2)	0.0801 (18)	0.0465 (17)	0.0148 (15)	0.0063 (14)
C31	0.0844 (18)	0.0739 (18)	0.0670 (15)	0.0241 (13)	0.0152 (13)	0.0044 (12)
C32	0.0633 (13)	0.0705 (16)	0.0566 (12)	0.0230 (11)	0.0145 (10)	0.0043 (10)

Geometric parameters (Å, º)

O11—C10	1.233 (2)	C13—H13A	0.9592
O23—C22	1.341 (2)	C13—H13B	0.9614
O23—N24	1.415 (3)	C14—C15	1.349 (4)
N7—C10	1.352 (3)	C14—C19	1.382 (4)
N7—C1	1.439 (2)	C15—C16	1.361 (5)
N7—C8	1.467 (3)	C15—H15	0.9603
N20—C6	1.386 (3)	C16—C17	1.329 (5)
N20—C21	1.450 (3)	C16—H16	0.9610
N20—H20	0.9971	C17—C18	1.364 (5)
N24—C25	1.300 (3)	C17—H17	0.9612
C1—C2	1.380 (3)	C18—C19	1.380 (5)
C1—C6	1.395 (3)	C18—H18	0.9599
C2—C3	1.371 (3)	C19—H19	0.9598
C2—H2	0.9609	C21—C22	1.489 (3)
C3—C4	1.354 (4)	C21—H21A	0.9598
C3—H3	0.9596	C21—H21B	0.9593
C4—C5	1.379 (4)	C22—C26	1.331 (3)
C4—H4	0.9583	C25—C26	1.414 (3)
C5—C6	1.397 (3)	C25—C27	1.465 (3)
C5—H5	0.9596	C26—H26	0.9599
C8—C9	1.500 (4)	C27—C32	1.384 (3)
C8—H8A	0.9596	C27—C28	1.385 (3)
C8—H8B	0.9602	C28—C29	1.372 (4)
C9—H9A	0.9595	C28—H28	0.9598
C9—H9B	0.9601	C29—C30	1.359 (4)
C9—H9C	0.9595	C29—H29	0.9612
C10—C12	1.493 (3)	C30—C31	1.371 (4)
C12—C13	1.469 (4)	C30—H30	0.9599
C12—H12A	0.9595	C31—C32	1.375 (4)
C12—H12B	0.9595	C31—H31	0.9596
C13—C14	1.498 (4)	C32—H32	0.9596
C22—O23—N24	108.41 (17)	H13A—C13—H13B	109.4
C10—N7—C1	122.17 (18)	C15—C14—C19	116.3 (3)
C10—N7—C8	120.97 (18)	C15—C14—C13	120.6 (3)
C1—N7—C8	116.30 (17)	C19—C14—C13	123.0 (3)
C6—N20—C21	121.31 (17)	C14—C15—C16	122.4 (3)
C6—N20—H20	117.2	C14—C15—H15	117.9
C21—N20—H20	113.6	C16—C15—H15	119.7
C25—N24—O23	105.71 (17)	C17—C16—C15	121.4 (3)
C2—C1—C6	120.81 (19)	C17—C16—H16	121.9
C2—C1—N7	120.09 (18)	C15—C16—H16	116.7
C6—C1—N7	119.06 (17)	C16—C17—C18	118.8 (3)
C3—C2—C1	120.6 (2)	C16—C17—H17	118.1
C3—C2—H2	120.3	C18—C17—H17	123.1
C1—C2—H2	119.1	C17—C18—C19	120.0 (3)
C4—C3—C2	119.4 (2)	C17—C18—H18	119.4
C4—C3—H3	119.9	C19—C18—H18	120.6
C2—C3—H3	120.6	C18—C19—C14	121.1 (3)
C3—C4—C5	121.2 (2)	C18—C19—H19	120.4
C3—C4—H4	120.1	C14—C19—H19	118.5
C5—C4—H4	118.7	N20—C21—C22	113.49 (16)
C4—C5—C6	120.7 (2)	N20—C21—H21A	108.5
C4—C5—H5	119.2	C22—C21—H21A	109.0
C6—C5—H5	120.1	N20—C21—H21B	107.1
N20—C6—C1	119.86 (17)	C22—C21—H21B	109.1
N20—C6—C5	122.87 (19)	H21A—C21—H21B	109.5
C1—C6—C5	117.20 (19)	C26—C22—O23	109.4 (2)
N7—C8—C9	113.1 (2)	C26—C22—C21	132.12 (19)
N7—C8—H8A	109.1	O23—C22—C21	118.5 (2)
C9—C8—H8A	108.5	N24—C25—C26	110.6 (2)
N7—C8—H8B	108.6	N24—C25—C27	121.39 (19)
C9—C8—H8B	108.0	C26—C25—C27	128.0 (2)
H8A—C8—H8B	109.5	C22—C26—C25	105.87 (19)
C8—C9—H9A	109.4	C22—C26—H26	119.9
C8—C9—H9B	109.2	C25—C26—H26	134.3
H9A—C9—H9B	109.5	C32—C27—C28	117.3 (2)
C8—C9—H9C	109.8	C32—C27—C25	120.8 (2)
H9A—C9—H9C	109.6	C28—C27—C25	121.9 (2)
H9B—C9—H9C	109.4	C29—C28—C27	121.1 (3)
O11—C10—N7	121.3 (2)	C29—C28—H28	120.5
O11—C10—C12	122.4 (2)	C27—C28—H28	118.4
N7—C10—C12	116.24 (18)	C30—C29—C28	121.0 (3)
C13—C12—C10	115.5 (2)	C30—C29—H29	119.9
C13—C12—H12A	107.9	C28—C29—H29	119.1
C10—C12—H12A	107.1	C29—C30—C31	118.9 (3)
C13—C12—H12B	109.4	C29—C30—H30	120.0
C10—C12—H12B	107.2	C31—C30—H30	121.0
H12A—C12—H12B	109.6	C30—C31—C32	120.6 (3)
C12—C13—C14	114.0 (2)	C30—C31—H31	121.3
C12—C13—H13A	109.5	C32—C31—H31	118.1
C14—C13—H13A	108.9	C31—C32—C27	121.0 (2)
C12—C13—H13B	108.0	C31—C32—H32	119.4
C14—C13—H13B	107.0	C27—C32—H32	119.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N20—H20···O11^i	1.00 (1)	2.06 (1)	2.951 (3)	148 (1)

Symmetry code: (i) −x−1, −y, −z.