N-Acetyl-N-[2,4-dicyano-1-(4-meth-oxy-phen-yl)-9,10-dihydro-phenanthren-3-yl]acetamide.

In the title compound, C(27)H(21)N(3)O(3), the cyclo-hexa-1,3-diene ring has a screw-boat conformation, and the fused ring system is folded, the dihedral angle between the outer benzene rings being 27.61 (6)°. The N-acetyl-acetamide residue (r.m.s. deviation = 0.0935 Å) has an anti conformation and is essentially perpendicular to the benzene ring to which it is connected [dihedral angle = 89.14 (6)°]; the meth-oxy-benzene group is also twisted out of this ring [dihedral angle = 59.47 (7)°]. The three-dimensional architecture is consolidated by C-H⋯O and C-H⋯π inter-actions.

Related literature

For background to the biological activity of related phenanthrene compounds, see: Wang et al. (2010 ▶); Rostom et al. (2011 ▶). For related structures, see: Asiri et al. (2011 ▶); Al-Youbi et al. (2012 ▶). For additional conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C27H21N3O3

M = 435.47

Orthorhombic,

a = 8.3321 (4) Å

b = 19.4037 (11) Å

c = 27.5887 (14) Å

V = 4460.4 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.40 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.966, T max = 0.991

11528 measured reflections

5106 independent reflections

3488 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.166

S = 1.02

5106 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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: X-SEED (Barbour, 2001 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201210X/lh5437sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201210X/lh5437Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201210X/lh5437Isup3.cml

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

C27H21N3O3	F(000) = 1824
Mr = 435.47	Dx = 1.297 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2867 reflections
a = 8.3321 (4) Å	θ = 2.4–27.5°
b = 19.4037 (11) Å	µ = 0.09 mm−1
c = 27.5887 (14) Å	T = 100 K
V = 4460.4 (4) Å3	Prism, light-brown
Z = 8	0.40 × 0.20 × 0.10 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	5106 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3488 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.041
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.6°
ω scan	h = −10→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→25
Tmin = 0.966, Tmax = 0.991	l = −35→21
11528 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0647P)2 + 2.7824P] where P = (Fo2 + 2Fc2)/3
5106 reflections	(Δ/σ)max = 0.001
300 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.2784 (2)	0.49381 (8)	0.63579 (6)	0.0326 (4)
O2	−0.1406 (2)	0.59674 (9)	0.61677 (7)	0.0403 (5)
O3	0.0262 (2)	0.10850 (9)	0.47080 (6)	0.0332 (4)
N1	0.0632 (3)	0.51602 (11)	0.74941 (8)	0.0433 (6)
N2	0.0092 (2)	0.49981 (9)	0.62945 (7)	0.0213 (4)
N3	−0.0310 (3)	0.41448 (11)	0.51859 (8)	0.0392 (6)
C1	0.0157 (2)	0.28935 (11)	0.67074 (8)	0.0189 (5)
C2	0.0293 (3)	0.21508 (11)	0.68718 (8)	0.0210 (5)
H2A	0.0725	0.1866	0.6604	0.025*
H2B	−0.0785	0.1973	0.6956	0.025*
C3	0.1396 (3)	0.20966 (11)	0.73113 (8)	0.0217 (5)
H3A	0.1433	0.1613	0.7426	0.026*
H3B	0.2497	0.2237	0.7220	0.026*
C4	0.0780 (2)	0.25552 (11)	0.77096 (8)	0.0205 (5)
C5	0.0778 (3)	0.23518 (12)	0.81939 (8)	0.0245 (5)
H5	0.1225	0.1918	0.8280	0.029*
C6	0.0133 (3)	0.27708 (13)	0.85540 (8)	0.0273 (5)
H6	0.0167	0.2629	0.8883	0.033*
C7	−0.0557 (3)	0.33955 (13)	0.84298 (8)	0.0269 (5)
H7	−0.1024	0.3677	0.8674	0.032*
C8	−0.0567 (3)	0.36109 (12)	0.79510 (8)	0.0241 (5)
H8	−0.1048	0.4039	0.7869	0.029*
C9	0.0125 (3)	0.32038 (11)	0.75861 (8)	0.0206 (5)
C10	0.0137 (3)	0.34111 (11)	0.70697 (8)	0.0200 (5)
C11	0.0169 (3)	0.41078 (11)	0.69237 (8)	0.0202 (5)
C12	0.0090 (3)	0.42839 (11)	0.64368 (8)	0.0222 (5)
C13	0.0038 (3)	0.37711 (11)	0.60844 (8)	0.0204 (5)
C14	0.0111 (2)	0.30663 (11)	0.62148 (8)	0.0189 (4)
C15	0.0407 (3)	0.46807 (12)	0.72585 (9)	0.0295 (5)
C16	−0.2878 (3)	0.49315 (14)	0.63111 (11)	0.0379 (6)
H16A	−0.3823	0.5230	0.6288	0.057*
H16B	−0.2863	0.4705	0.6629	0.057*
H16C	−0.2922	0.4582	0.6055	0.057*
C17	−0.1384 (3)	0.53571 (12)	0.62517 (9)	0.0288 (5)
C18	0.1648 (3)	0.52930 (12)	0.62423 (8)	0.0247 (5)
C19	0.1828 (3)	0.60013 (12)	0.60405 (9)	0.0336 (6)
H19A	0.2963	0.6091	0.5971	0.050*
H19B	0.1436	0.6338	0.6277	0.050*
H19C	0.1204	0.6040	0.5741	0.050*
C20	−0.0140 (3)	0.39733 (12)	0.55834 (9)	0.0268 (5)
C21	0.0139 (3)	0.25367 (11)	0.58236 (8)	0.0200 (5)
C22	0.1360 (3)	0.25280 (12)	0.54760 (8)	0.0251 (5)
H22	0.2192	0.2862	0.5492	0.030*
C23	0.1380 (3)	0.20432 (12)	0.51101 (8)	0.0266 (5)
H23	0.2224	0.2042	0.4879	0.032*
C24	0.0150 (3)	0.15530 (12)	0.50807 (8)	0.0243 (5)
C25	−0.1080 (3)	0.15542 (11)	0.54194 (8)	0.0223 (5)
H25	−0.1922	0.1226	0.5399	0.027*
C26	−0.1067 (3)	0.20427 (11)	0.57908 (8)	0.0205 (5)
H26	−0.1900	0.2038	0.6026	0.025*
C27	−0.1006 (3)	0.06072 (15)	0.46578 (10)	0.0420 (7)
H27A	−0.0789	0.0304	0.4381	0.063*
H27B	−0.2014	0.0855	0.4603	0.063*
H27C	−0.1093	0.0331	0.4954	0.063*

	U11	U22	U33	U12	U13	U23
O1	0.0286 (9)	0.0278 (9)	0.0413 (10)	−0.0001 (7)	−0.0040 (8)	0.0001 (8)
O2	0.0445 (11)	0.0217 (9)	0.0548 (12)	0.0075 (8)	−0.0187 (9)	−0.0036 (8)
O3	0.0439 (10)	0.0312 (9)	0.0244 (9)	−0.0042 (8)	0.0033 (8)	−0.0079 (7)
N1	0.0689 (17)	0.0307 (12)	0.0303 (11)	−0.0073 (12)	−0.0001 (12)	−0.0032 (10)
N2	0.0276 (10)	0.0130 (9)	0.0234 (9)	0.0005 (7)	−0.0038 (8)	0.0006 (7)
N3	0.0618 (15)	0.0267 (11)	0.0291 (12)	−0.0033 (11)	−0.0083 (11)	0.0036 (9)
C1	0.0163 (10)	0.0169 (11)	0.0235 (11)	−0.0004 (8)	0.0023 (9)	0.0018 (9)
C2	0.0236 (11)	0.0179 (11)	0.0217 (11)	0.0010 (9)	−0.0001 (9)	0.0039 (9)
C3	0.0211 (11)	0.0203 (11)	0.0237 (11)	0.0020 (9)	−0.0015 (9)	0.0035 (9)
C4	0.0156 (10)	0.0226 (11)	0.0232 (11)	−0.0022 (8)	−0.0014 (9)	0.0019 (9)
C5	0.0209 (11)	0.0274 (12)	0.0252 (12)	0.0025 (9)	−0.0028 (9)	0.0064 (10)
C6	0.0261 (12)	0.0351 (14)	0.0208 (11)	−0.0021 (10)	−0.0005 (10)	0.0044 (10)
C7	0.0270 (12)	0.0300 (13)	0.0238 (11)	0.0001 (10)	0.0016 (10)	−0.0025 (10)
C8	0.0230 (11)	0.0227 (12)	0.0267 (12)	−0.0003 (9)	0.0006 (10)	−0.0011 (9)
C9	0.0177 (10)	0.0205 (11)	0.0237 (11)	−0.0018 (9)	−0.0014 (9)	0.0006 (9)
C10	0.0170 (10)	0.0199 (11)	0.0230 (11)	0.0005 (8)	−0.0003 (9)	0.0023 (9)
C11	0.0223 (11)	0.0178 (11)	0.0204 (11)	0.0010 (9)	−0.0012 (9)	−0.0010 (9)
C12	0.0238 (11)	0.0167 (11)	0.0261 (12)	0.0015 (9)	−0.0022 (9)	−0.0001 (9)
C13	0.0226 (11)	0.0190 (11)	0.0196 (10)	−0.0014 (9)	−0.0016 (9)	0.0005 (8)
C14	0.0182 (10)	0.0171 (11)	0.0215 (10)	−0.0010 (8)	0.0009 (9)	0.0015 (9)
C15	0.0393 (14)	0.0232 (12)	0.0259 (12)	−0.0004 (11)	0.0007 (11)	0.0005 (10)
C16	0.0293 (13)	0.0353 (15)	0.0490 (16)	0.0035 (11)	−0.0028 (12)	0.0001 (12)
C17	0.0349 (13)	0.0248 (13)	0.0266 (12)	0.0042 (10)	−0.0079 (11)	−0.0037 (10)
C18	0.0326 (13)	0.0219 (12)	0.0195 (11)	−0.0005 (10)	−0.0038 (10)	−0.0044 (9)
C19	0.0438 (15)	0.0241 (13)	0.0328 (13)	−0.0054 (11)	−0.0042 (12)	0.0029 (10)
C20	0.0372 (13)	0.0158 (11)	0.0273 (12)	−0.0028 (10)	−0.0025 (11)	0.0003 (9)
C21	0.0236 (11)	0.0172 (10)	0.0191 (10)	0.0040 (9)	−0.0006 (9)	0.0045 (8)
C22	0.0266 (12)	0.0220 (12)	0.0269 (12)	−0.0024 (9)	0.0037 (10)	0.0038 (9)
C23	0.0307 (12)	0.0248 (12)	0.0244 (11)	0.0008 (10)	0.0086 (10)	0.0034 (9)
C24	0.0330 (13)	0.0227 (11)	0.0173 (10)	0.0040 (10)	−0.0006 (10)	0.0000 (9)
C25	0.0223 (11)	0.0219 (11)	0.0226 (11)	−0.0016 (9)	−0.0007 (9)	−0.0004 (9)
C26	0.0220 (11)	0.0203 (11)	0.0193 (10)	0.0014 (9)	0.0017 (9)	0.0009 (9)
C27	0.0426 (16)	0.0434 (16)	0.0400 (15)	−0.0022 (13)	−0.0020 (13)	−0.0141 (13)

O1—C18	1.213 (3)	C10—C11	1.411 (3)
O2—C17	1.207 (3)	C11—C12	1.388 (3)
O3—C24	1.375 (3)	C11—C15	1.459 (3)
O3—C27	1.412 (3)	C12—C13	1.392 (3)
N1—C15	1.150 (3)	C13—C14	1.415 (3)
N2—C17	1.418 (3)	C13—C20	1.445 (3)
N2—C18	1.425 (3)	C14—C21	1.490 (3)
N2—C12	1.440 (3)	C16—C17	1.503 (4)
N3—C20	1.155 (3)	C16—H16A	0.9800
C1—C14	1.400 (3)	C16—H16B	0.9800
C1—C10	1.417 (3)	C16—H16C	0.9800
C1—C2	1.515 (3)	C18—C19	1.490 (3)
C2—C3	1.525 (3)	C19—H19A	0.9800
C2—H2A	0.9900	C19—H19B	0.9800
C2—H2B	0.9900	C19—H19C	0.9800
C3—C4	1.504 (3)	C21—C26	1.392 (3)
C3—H3A	0.9900	C21—C22	1.399 (3)
C3—H3B	0.9900	C22—C23	1.380 (3)
C4—C5	1.393 (3)	C22—H22	0.9500
C4—C9	1.414 (3)	C23—C24	1.400 (3)
C5—C6	1.392 (3)	C23—H23	0.9500
C5—H5	0.9500	C24—C25	1.387 (3)
C6—C7	1.385 (3)	C25—C26	1.396 (3)
C6—H6	0.9500	C25—H25	0.9500
C7—C8	1.385 (3)	C26—H26	0.9500
C7—H7	0.9500	C27—H27A	0.9800
C8—C9	1.403 (3)	C27—H27B	0.9800
C8—H8	0.9500	C27—H27C	0.9800
C9—C10	1.481 (3)
C24—O3—C27	117.15 (19)	C14—C13—C20	120.66 (19)
C17—N2—C18	125.69 (19)	C1—C14—C13	118.62 (19)
C17—N2—C12	119.62 (19)	C1—C14—C21	122.50 (19)
C18—N2—C12	114.52 (18)	C13—C14—C21	118.87 (19)
C14—C1—C10	120.98 (19)	N1—C15—C11	175.0 (3)
C14—C1—C2	121.35 (19)	C17—C16—H16A	109.5
C10—C1—C2	117.63 (19)	C17—C16—H16B	109.5
C1—C2—C3	110.40 (18)	H16A—C16—H16B	109.5
C1—C2—H2A	109.6	C17—C16—H16C	109.5
C3—C2—H2A	109.6	H16A—C16—H16C	109.5
C1—C2—H2B	109.6	H16B—C16—H16C	109.5
C3—C2—H2B	109.6	O2—C17—N2	120.8 (2)
H2A—C2—H2B	108.1	O2—C17—C16	123.2 (2)
C4—C3—C2	109.55 (17)	N2—C17—C16	116.1 (2)
C4—C3—H3A	109.8	O1—C18—N2	117.1 (2)
C2—C3—H3A	109.8	O1—C18—C19	122.9 (2)
C4—C3—H3B	109.8	N2—C18—C19	120.0 (2)
C2—C3—H3B	109.8	C18—C19—H19A	109.5
H3A—C3—H3B	108.2	C18—C19—H19B	109.5
C5—C4—C9	118.9 (2)	H19A—C19—H19B	109.5
C5—C4—C3	122.2 (2)	C18—C19—H19C	109.5
C9—C4—C3	118.85 (19)	H19A—C19—H19C	109.5
C6—C5—C4	121.3 (2)	H19B—C19—H19C	109.5
C6—C5—H5	119.3	N3—C20—C13	178.5 (3)
C4—C5—H5	119.3	C26—C21—C22	118.2 (2)
C7—C6—C5	119.7 (2)	C26—C21—C14	120.73 (19)
C7—C6—H6	120.2	C22—C21—C14	121.1 (2)
C5—C6—H6	120.2	C23—C22—C21	121.2 (2)
C6—C7—C8	120.2 (2)	C23—C22—H22	119.4
C6—C7—H7	119.9	C21—C22—H22	119.4
C8—C7—H7	119.9	C22—C23—C24	119.8 (2)
C7—C8—C9	120.8 (2)	C22—C23—H23	120.1
C7—C8—H8	119.6	C24—C23—H23	120.1
C9—C8—H8	119.6	O3—C24—C25	123.7 (2)
C8—C9—C4	119.1 (2)	O3—C24—C23	116.3 (2)
C8—C9—C10	122.7 (2)	C25—C24—C23	120.0 (2)
C4—C9—C10	118.10 (19)	C24—C25—C26	119.4 (2)
C11—C10—C1	118.5 (2)	C24—C25—H25	120.3
C11—C10—C9	122.35 (19)	C26—C25—H25	120.3
C1—C10—C9	119.11 (19)	C21—C26—C25	121.4 (2)
C12—C11—C10	120.8 (2)	C21—C26—H26	119.3
C12—C11—C15	115.6 (2)	C25—C26—H26	119.3
C10—C11—C15	123.5 (2)	O3—C27—H27A	109.5
C11—C12—C13	120.1 (2)	O3—C27—H27B	109.5
C11—C12—N2	120.04 (19)	H27A—C27—H27B	109.5
C13—C12—N2	119.8 (2)	O3—C27—H27C	109.5
C12—C13—C14	120.8 (2)	H27A—C27—H27C	109.5
C12—C13—C20	118.5 (2)	H27B—C27—H27C	109.5
C14—C1—C2—C3	141.1 (2)	C11—C12—C13—C14	−1.8 (3)
C10—C1—C2—C3	−36.6 (3)	N2—C12—C13—C14	177.00 (19)
C1—C2—C3—C4	56.6 (2)	C11—C12—C13—C20	176.4 (2)
C2—C3—C4—C5	139.1 (2)	N2—C12—C13—C20	−4.8 (3)
C2—C3—C4—C9	−38.3 (3)	C10—C1—C14—C13	−0.2 (3)
C9—C4—C5—C6	0.6 (3)	C2—C1—C14—C13	−177.90 (19)
C3—C4—C5—C6	−176.9 (2)	C10—C1—C14—C21	179.67 (19)
C4—C5—C6—C7	1.6 (3)	C2—C1—C14—C21	2.0 (3)
C5—C6—C7—C8	−1.7 (4)	C12—C13—C14—C1	3.1 (3)
C6—C7—C8—C9	−0.3 (3)	C20—C13—C14—C1	−175.0 (2)
C7—C8—C9—C4	2.5 (3)	C12—C13—C14—C21	−176.8 (2)
C7—C8—C9—C10	179.8 (2)	C20—C13—C14—C21	5.0 (3)
C5—C4—C9—C8	−2.6 (3)	C18—N2—C17—O2	−0.6 (3)
C3—C4—C9—C8	174.98 (19)	C12—N2—C17—O2	174.6 (2)
C5—C4—C9—C10	−179.99 (19)	C18—N2—C17—C16	178.7 (2)
C3—C4—C9—C10	−2.4 (3)	C12—N2—C17—C16	−6.1 (3)
C14—C1—C10—C11	−3.8 (3)	C17—N2—C18—O1	169.7 (2)
C2—C1—C10—C11	173.92 (19)	C12—N2—C18—O1	−5.6 (3)
C14—C1—C10—C9	177.67 (19)	C17—N2—C18—C19	−11.9 (3)
C2—C1—C10—C9	−4.6 (3)	C12—N2—C18—C19	172.7 (2)
C8—C9—C10—C11	29.9 (3)	C1—C14—C21—C26	60.5 (3)
C4—C9—C10—C11	−152.8 (2)	C13—C14—C21—C26	−119.5 (2)
C8—C9—C10—C1	−151.6 (2)	C1—C14—C21—C22	−120.4 (2)
C4—C9—C10—C1	25.7 (3)	C13—C14—C21—C22	59.5 (3)
C1—C10—C11—C12	5.2 (3)	C26—C21—C22—C23	−0.2 (3)
C9—C10—C11—C12	−176.4 (2)	C14—C21—C22—C23	−179.3 (2)
C1—C10—C11—C15	−170.0 (2)	C21—C22—C23—C24	0.6 (4)
C9—C10—C11—C15	8.5 (3)	C27—O3—C24—C25	3.7 (3)
C10—C11—C12—C13	−2.4 (3)	C27—O3—C24—C23	−177.0 (2)
C15—C11—C12—C13	173.1 (2)	C22—C23—C24—O3	−179.5 (2)
C10—C11—C12—N2	178.78 (19)	C22—C23—C24—C25	−0.2 (3)
C15—C11—C12—N2	−5.7 (3)	O3—C24—C25—C26	178.6 (2)
C17—N2—C12—C11	−89.7 (3)	C23—C24—C25—C26	−0.7 (3)
C18—N2—C12—C11	86.0 (2)	C22—C21—C26—C25	−0.7 (3)
C17—N2—C12—C13	91.5 (3)	C14—C21—C26—C25	178.4 (2)
C18—N2—C12—C13	−92.8 (2)	C24—C25—C26—C21	1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.40	3.255 (3)	150
C25—H25···O2ii	0.95	2.59	3.154 (3)	119
C26—H26···O2ii	0.95	2.54	3.141 (3)	121
C27—H27A···O1iii	0.98	2.41	3.160 (3)	133
C3—H3B···Cg1iv	0.99	2.74	3.696 (3)	164
C19—H19A···Cg2v	0.98	2.82	3.618 (3)	139

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C4–C9 and C21–C26 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2i	0.95	2.40	3.255 (3)	150
C25—H25⋯O2ii	0.95	2.59	3.154 (3)	119
C26—H26⋯O2ii	0.95	2.54	3.141 (3)	121
C27—H27A⋯O1iii	0.98	2.41	3.160 (3)	133
C3—H3B⋯Cg1iv	0.99	2.74	3.696 (3)	164
C19—H19A⋯Cg2v	0.98	2.82	3.618 (3)	139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .