(4R,5R,10S)-N-(4-Bromo-phen-yl)dehydro-abietamide.

The title compound, C(26)H(32)BrNO, the ring with the amide unit possesses a chair conformation with the two methyl groups in axial positions..

Related literature

For the synthesis and biological activity of dehydro­abietamide derivatives, see: Ntokos et al. (1973 ▶); Sepulveda et al. (2005 ▶); Fujita et al. (1991 ▶). For related structures see: Rao et al. (2006 ▶, 2007 ▶).

Experimental

Crystal data

C26H32BrNO

M = 454.44

Orthorhombic,

a = 5.9640 (12) Å

b = 11.750 (2) Å

c = 32.758 (7) Å

V = 2295.6 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.81 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.714, T max = 0.840

4770 measured reflections

4143 independent reflections

1931 reflections with I > 2σ(I)

R int = 0.063

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.133

S = 1.00

4143 reflections

257 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.34 e Å−3

Absolute structure: Flack (1983 ▶), 1699 Friedel pairs

Flack parameter: −0.003 (16)

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809049575/ng2678sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809049575/ng2678Isup2.hkl

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

C26H32BrNO	Dx = 1.315 Mg m−3
Mr = 454.44	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 5.9640 (12) Å	θ = 10–13°
b = 11.750 (2) Å	µ = 1.81 mm−1
c = 32.758 (7) Å	T = 293 K
V = 2295.6 (8) Å3	Block, colourless
Z = 4	0.20 × 0.10 × 0.10 mm
F(000) = 952

Enraf–Nonius CAD-4 diffractometer	1931 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.063
graphite	θmax = 25.3°, θmin = 1.2°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = 0→14
Tmin = 0.714, Tmax = 0.840	l = −39→39
4770 measured reflections	3 standard reflections every 200 reflections
4143 independent reflections	intensity decay: 1%

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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.133	w = 1/[σ2(Fo2) + (0.048P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
4143 reflections	Δρmax = 0.32 e Å−3
257 parameters	Δρmin = −0.34 e Å−3
0 restraints	Absolute structure: Flack (1983), 1699 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.003 (16)

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	Uiso*/Ueq
Br	0.81958 (18)	0.68193 (7)	0.09535 (2)	0.0947 (4)
N	0.8080 (10)	1.0580 (5)	−0.03060 (15)	0.0532 (14)
H0A	0.9407	1.0744	−0.0390	0.064*
O	0.4404 (8)	1.1045 (4)	−0.03859 (15)	0.0639 (14)
C1	−0.1942 (15)	1.1802 (8)	−0.2890 (2)	0.109
H1A	−0.2768	1.1527	−0.3121	0.164*
H1B	−0.1996	1.2618	−0.2885	0.164*
H1C	−0.2592	1.1506	−0.2644	0.164*
C2	0.1482 (15)	1.1731 (9)	−0.3320 (2)	0.122 (4)
H2A	0.0551	1.1471	−0.3540	0.183*
H2B	0.2929	1.1377	−0.3339	0.183*
H2C	0.1650	1.2542	−0.3337	0.183*
C3	0.0417 (14)	1.1424 (8)	−0.2921 (2)	0.094 (3)
H3A	0.0389	1.0591	−0.2910	0.112*
C4	0.1823 (13)	1.1816 (8)	−0.2558 (2)	0.069 (2)
C5	0.2310 (12)	1.2951 (8)	−0.2487 (2)	0.067 (2)
H5A	0.1777	1.3507	−0.2665	0.081*
C6	0.3610 (11)	1.3266 (6)	−0.21477 (18)	0.0565 (18)
H6A	0.3951	1.4029	−0.2105	0.068*
C7	0.4407 (11)	1.2442 (6)	−0.18691 (19)	0.0487 (18)
C8	0.3956 (12)	1.1298 (6)	−0.1947 (2)	0.055 (2)
C9	0.2662 (13)	1.1021 (7)	−0.2288 (2)	0.064 (2)
H9A	0.2345	1.0258	−0.2335	0.077*
C10	0.5908 (10)	1.2836 (5)	−0.15146 (18)	0.0399 (17)
C11	0.5900 (9)	1.1879 (5)	−0.11856 (17)	0.0398 (15)
H11A	0.4317	1.1781	−0.1114	0.048*
C12	0.6589 (13)	1.0742 (5)	−0.13792 (19)	0.0555 (19)
H12A	0.7988	1.0831	−0.1527	0.067*
H12B	0.6804	1.0172	−0.1169	0.067*
C13	0.4725 (14)	1.0366 (6)	−0.1672 (2)	0.068 (2)
H13A	0.5267	0.9738	−0.1837	0.081*
H13B	0.3459	1.0093	−0.1514	0.081*
C14	0.4971 (11)	1.3919 (5)	−0.13126 (18)	0.0486 (18)
H14A	0.5092	1.4546	−0.1504	0.058*
H14B	0.3393	1.3806	−0.1254	0.058*
C15	0.6185 (12)	1.4242 (5)	−0.09160 (19)	0.0575 (19)
H15A	0.7739	1.4421	−0.0975	0.069*
H15B	0.5491	1.4913	−0.0799	0.069*
C16	0.6080 (11)	1.3265 (6)	−0.06107 (18)	0.0535 (18)
H16A	0.4527	1.3132	−0.0537	0.064*
H16B	0.6879	1.3483	−0.0365	0.064*
C17	0.7083 (11)	1.2159 (5)	−0.0775 (2)	0.0470 (18)
C18	0.8244 (11)	1.3108 (6)	−0.17050 (17)	0.0611 (18)
H18A	0.8041	1.3499	−0.1960	0.092*
H18B	0.9045	1.2411	−0.1752	0.092*
H18C	0.9083	1.3580	−0.1521	0.092*
C19	0.9710 (10)	1.2251 (6)	−0.0809 (2)	0.073 (3)
H19A	1.0095	1.2840	−0.0999	0.110*
H19B	1.0310	1.1538	−0.0902	0.110*
H19C	1.0327	1.2429	−0.0546	0.110*
C20	0.6416 (14)	1.1207 (6)	−0.04718 (19)	0.0519 (18)
C21	0.7971 (13)	0.9705 (5)	−0.00191 (19)	0.0477 (17)
C22	0.9833 (12)	0.9004 (5)	0.0016 (2)	0.0580 (19)
H22A	1.1067	0.9120	−0.0153	0.070*
C23	0.9861 (13)	0.8142 (7)	0.0298 (2)	0.063 (2)
H23A	1.1096	0.7659	0.0311	0.075*
C24	0.8111 (16)	0.7978 (6)	0.05601 (19)	0.061 (2)
C25	0.6259 (13)	0.8674 (6)	0.05292 (19)	0.060 (2)
H25A	0.5046	0.8560	0.0703	0.072*
C26	0.6176 (12)	0.9541 (6)	0.02438 (19)	0.058 (2)
H26A	0.4924	1.0010	0.0228	0.069*

	U11	U22	U33	U12	U13	U23
Br	0.1378 (8)	0.0749 (5)	0.0715 (5)	0.0229 (6)	−0.0134 (6)	0.0208 (5)
N	0.032 (3)	0.072 (4)	0.055 (3)	0.014 (4)	0.001 (3)	0.012 (3)
O	0.032 (3)	0.089 (4)	0.070 (3)	−0.006 (3)	0.002 (3)	0.028 (3)
C1	0.109	0.109	0.109	0.000	0.000	0.000
C2	0.093 (7)	0.220 (11)	0.054 (5)	0.027 (10)	−0.007 (6)	−0.031 (7)
C3	0.084 (7)	0.140 (9)	0.057 (5)	0.005 (6)	−0.012 (5)	−0.021 (5)
C4	0.059 (5)	0.100 (6)	0.048 (4)	0.005 (7)	0.013 (4)	−0.013 (5)
C5	0.048 (5)	0.102 (7)	0.051 (4)	0.010 (5)	−0.004 (4)	0.019 (5)
C6	0.047 (5)	0.073 (5)	0.049 (4)	−0.007 (5)	0.005 (4)	0.010 (4)
C7	0.034 (4)	0.071 (5)	0.041 (4)	−0.004 (4)	0.008 (4)	0.010 (4)
C8	0.052 (5)	0.063 (5)	0.050 (4)	−0.003 (4)	−0.006 (4)	−0.009 (4)
C9	0.062 (6)	0.078 (5)	0.053 (4)	−0.007 (4)	0.001 (4)	−0.007 (4)
C10	0.027 (4)	0.054 (4)	0.039 (4)	−0.001 (3)	0.004 (3)	0.001 (3)
C11	0.019 (3)	0.055 (4)	0.045 (3)	−0.010 (4)	0.000 (3)	0.004 (4)
C12	0.060 (5)	0.049 (4)	0.058 (4)	0.001 (5)	0.003 (5)	0.012 (3)
C13	0.092 (6)	0.053 (5)	0.058 (5)	0.009 (5)	−0.011 (5)	0.005 (4)
C14	0.046 (4)	0.051 (4)	0.050 (4)	−0.004 (4)	0.006 (4)	0.007 (3)
C15	0.066 (5)	0.053 (4)	0.053 (4)	−0.003 (4)	−0.003 (5)	−0.003 (4)
C16	0.045 (5)	0.064 (4)	0.052 (4)	−0.008 (4)	0.000 (3)	−0.007 (4)
C17	0.027 (4)	0.057 (4)	0.057 (4)	−0.004 (4)	0.001 (4)	0.012 (3)
C18	0.042 (4)	0.082 (5)	0.059 (4)	−0.003 (5)	0.015 (4)	0.021 (4)
C19	0.028 (4)	0.113 (7)	0.079 (6)	−0.012 (5)	−0.011 (4)	0.018 (5)
C20	0.050 (5)	0.060 (4)	0.046 (4)	−0.005 (5)	−0.003 (4)	−0.004 (3)
C21	0.047 (4)	0.051 (4)	0.045 (4)	0.011 (4)	−0.015 (4)	−0.006 (3)
C22	0.052 (5)	0.057 (5)	0.066 (5)	0.009 (4)	−0.010 (4)	0.003 (4)
C23	0.065 (6)	0.058 (5)	0.064 (5)	0.017 (5)	−0.015 (4)	−0.006 (5)
C24	0.071 (5)	0.058 (5)	0.054 (4)	0.014 (5)	−0.005 (5)	−0.009 (4)
C25	0.068 (6)	0.064 (5)	0.047 (4)	−0.005 (5)	0.005 (4)	0.005 (4)
C26	0.051 (5)	0.065 (5)	0.057 (5)	0.013 (4)	0.006 (4)	0.006 (4)

Br—C24	1.876 (7)	C12—C13	1.534 (9)
N—C20	1.350 (8)	C12—H12A	0.9700
N—C21	1.394 (7)	C12—H12B	0.9700
N—H0A	0.8600	C13—H13A	0.9700
O—C20	1.247 (7)	C13—H13B	0.9700
C1—C3	1.478 (11)	C14—C15	1.535 (8)
C1—H1A	0.9600	C14—H14A	0.9700
C1—H1B	0.9600	C14—H14B	0.9700
C1—H1C	0.9600	C15—C16	1.524 (8)
C2—C3	1.498 (10)	C15—H15A	0.9700
C2—H2A	0.9600	C15—H15B	0.9700
C2—H2B	0.9600	C16—C17	1.528 (9)
C2—H2C	0.9600	C16—H16A	0.9700
C3—C4	1.525 (10)	C16—H16B	0.9700
C3—H3A	0.9800	C17—C20	1.548 (8)
C4—C9	1.382 (10)	C17—C19	1.574 (8)
C4—C5	1.385 (10)	C18—H18A	0.9600
C5—C6	1.406 (9)	C18—H18B	0.9600
C5—H5A	0.9300	C18—H18C	0.9600
C6—C7	1.413 (8)	C19—H19A	0.9600
C6—H6A	0.9300	C19—H19B	0.9600
C7—C8	1.394 (8)	C19—H19C	0.9600
C7—C10	1.538 (9)	C21—C22	1.387 (8)
C8—C9	1.396 (8)	C21—C26	1.388 (8)
C8—C13	1.489 (9)	C22—C23	1.372 (9)
C9—H9A	0.9300	C22—H22A	0.9300
C10—C14	1.540 (8)	C23—C24	1.365 (9)
C10—C11	1.557 (8)	C23—H23A	0.9300
C10—C18	1.559 (8)	C24—C25	1.378 (9)
C11—C12	1.535 (8)	C25—C26	1.383 (8)
C11—C17	1.555 (8)	C25—H25A	0.9300
C11—H11A	0.9800	C26—H26A	0.9300
C20—N—C21	129.7 (6)	C8—C13—H13B	109.0
C20—N—H0A	115.1	C12—C13—H13B	109.0
C21—N—H0A	115.1	H13A—C13—H13B	107.8
C3—C1—H1A	109.5	C15—C14—C10	113.4 (5)
C3—C1—H1B	109.5	C15—C14—H14A	108.9
H1A—C1—H1B	109.5	C10—C14—H14A	108.9
C3—C1—H1C	109.5	C15—C14—H14B	108.9
H1A—C1—H1C	109.5	C10—C14—H14B	108.9
H1B—C1—H1C	109.5	H14A—C14—H14B	107.7
C3—C2—H2A	109.5	C16—C15—C14	110.5 (5)
C3—C2—H2B	109.5	C16—C15—H15A	109.6
H2A—C2—H2B	109.5	C14—C15—H15A	109.6
C3—C2—H2C	109.5	C16—C15—H15B	109.6
H2A—C2—H2C	109.5	C14—C15—H15B	109.6
H2B—C2—H2C	109.5	H15A—C15—H15B	108.1
C1—C3—C2	113.0 (8)	C15—C16—C17	113.1 (5)
C1—C3—C4	112.3 (7)	C15—C16—H16A	108.9
C2—C3—C4	112.0 (7)	C17—C16—H16A	108.9
C1—C3—H3A	106.3	C15—C16—H16B	108.9
C2—C3—H3A	106.3	C17—C16—H16B	108.9
C4—C3—H3A	106.3	H16A—C16—H16B	107.8
C9—C4—C5	117.9 (7)	C16—C17—C20	106.7 (5)
C9—C4—C3	119.7 (8)	C16—C17—C11	107.9 (5)
C5—C4—C3	122.5 (8)	C20—C17—C11	106.6 (5)
C4—C5—C6	120.1 (7)	C16—C17—C19	110.9 (6)
C4—C5—H5A	119.9	C20—C17—C19	110.5 (6)
C6—C5—H5A	119.9	C11—C17—C19	113.9 (5)
C5—C6—C7	121.1 (7)	C10—C18—H18A	109.5
C5—C6—H6A	119.4	C10—C18—H18B	109.5
C7—C6—H6A	119.4	H18A—C18—H18B	109.5
C8—C7—C6	118.6 (6)	C10—C18—H18C	109.5
C8—C7—C10	122.7 (6)	H18A—C18—H18C	109.5
C6—C7—C10	118.5 (6)	H18B—C18—H18C	109.5
C7—C8—C9	118.5 (7)	C17—C19—H19A	109.5
C7—C8—C13	122.7 (6)	C17—C19—H19B	109.5
C9—C8—C13	118.8 (7)	H19A—C19—H19B	109.5
C4—C9—C8	123.8 (7)	C17—C19—H19C	109.5
C4—C9—H9A	118.1	H19A—C19—H19C	109.5
C8—C9—H9A	118.1	H19B—C19—H19C	109.5
C7—C10—C14	111.2 (5)	O—C20—N	122.2 (7)
C7—C10—C11	107.7 (5)	O—C20—C17	120.1 (7)
C14—C10—C11	107.3 (5)	N—C20—C17	117.6 (7)
C7—C10—C18	106.3 (5)	C22—C21—C26	118.9 (6)
C14—C10—C18	109.0 (5)	C22—C21—N	117.1 (7)
C11—C10—C18	115.3 (5)	C26—C21—N	123.9 (7)
C12—C11—C17	114.8 (5)	C23—C22—C21	120.2 (7)
C12—C11—C10	110.0 (5)	C23—C22—H22A	119.9
C17—C11—C10	116.4 (5)	C21—C22—H22A	119.9
C12—C11—H11A	104.7	C24—C23—C22	121.2 (7)
C17—C11—H11A	104.7	C24—C23—H23A	119.4
C10—C11—H11A	104.7	C22—C23—H23A	119.4
C13—C12—C11	108.4 (6)	C23—C24—C25	118.9 (6)
C13—C12—H12A	110.0	C23—C24—Br	120.9 (6)
C11—C12—H12A	110.0	C25—C24—Br	120.2 (6)
C13—C12—H12B	110.0	C24—C25—C26	121.0 (7)
C11—C12—H12B	110.0	C24—C25—H25A	119.5
H12A—C12—H12B	108.4	C26—C25—H25A	119.5
C8—C13—C12	112.9 (6)	C25—C26—C21	119.7 (7)
C8—C13—H13A	109.0	C25—C26—H26A	120.2
C12—C13—H13A	109.0	C21—C26—H26A	120.2
C1—C3—C4—C9	113.1 (9)	C7—C10—C14—C15	170.8 (5)
C2—C3—C4—C9	−118.5 (9)	C11—C10—C14—C15	53.2 (6)
C1—C3—C4—C5	−67.0 (11)	C18—C10—C14—C15	−72.3 (6)
C2—C3—C4—C5	61.4 (11)	C10—C14—C15—C16	−57.3 (7)
C9—C4—C5—C6	−0.3 (11)	C14—C15—C16—C17	57.7 (7)
C3—C4—C5—C6	179.8 (7)	C15—C16—C17—C20	−168.5 (6)
C4—C5—C6—C7	−1.2 (10)	C15—C16—C17—C11	−54.3 (7)
C5—C6—C7—C8	2.6 (10)	C15—C16—C17—C19	71.0 (7)
C5—C6—C7—C10	177.3 (6)	C12—C11—C17—C16	−175.8 (5)
C6—C7—C8—C9	−2.5 (10)	C10—C11—C17—C16	53.7 (7)
C10—C7—C8—C9	−176.9 (6)	C12—C11—C17—C20	−61.5 (7)
C6—C7—C8—C13	179.9 (6)	C10—C11—C17—C20	168.0 (5)
C10—C7—C8—C13	5.4 (11)	C12—C11—C17—C19	60.7 (7)
C5—C4—C9—C8	0.4 (11)	C10—C11—C17—C19	−69.9 (7)
C3—C4—C9—C8	−179.7 (7)	C21—N—C20—O	−1.7 (11)
C7—C8—C9—C4	1.0 (11)	C21—N—C20—C17	177.8 (6)
C13—C8—C9—C4	178.8 (7)	C16—C17—C20—O	55.3 (8)
C8—C7—C10—C14	−141.0 (6)	C11—C17—C20—O	−59.8 (8)
C6—C7—C10—C14	44.5 (7)	C19—C17—C20—O	176.0 (6)
C8—C7—C10—C11	−23.7 (8)	C16—C17—C20—N	−124.2 (6)
C6—C7—C10—C11	161.9 (5)	C11—C17—C20—N	120.7 (6)
C8—C7—C10—C18	100.4 (7)	C19—C17—C20—N	−3.5 (8)
C6—C7—C10—C18	−74.0 (8)	C20—N—C21—C22	162.9 (6)
C7—C10—C11—C12	54.4 (7)	C20—N—C21—C26	−20.7 (10)
C14—C10—C11—C12	174.2 (5)	C26—C21—C22—C23	1.9 (10)
C18—C10—C11—C12	−64.0 (7)	N—C21—C22—C23	178.6 (6)
C7—C10—C11—C17	−172.8 (5)	C21—C22—C23—C24	−2.5 (11)
C14—C10—C11—C17	−53.0 (7)	C22—C23—C24—C25	2.1 (11)
C18—C10—C11—C17	68.8 (7)	C22—C23—C24—Br	−178.5 (5)
C17—C11—C12—C13	158.1 (5)	C23—C24—C25—C26	−1.3 (11)
C10—C11—C12—C13	−68.2 (6)	Br—C24—C25—C26	179.3 (5)
C7—C8—C13—C12	−17.0 (10)	C24—C25—C26—C21	0.8 (10)
C9—C8—C13—C12	165.4 (6)	C22—C21—C26—C25	−1.1 (10)
C11—C12—C13—C8	47.0 (7)	N—C21—C26—C25	−177.5 (6)