3-Amino-1-(3,4-dimeth-oxy-phen-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

In the title compound, C(24)H(19)N(3)O(2), the partially saturated ring adopts a distorted half-chair conformation with the methyl-ene-C atom closest to the amino-benzene ring lying 0.664 (3) Å out of the plane defined by the five remaining atoms (r.m.s. deviation = 0.1429 Å. The dihedral angle [32.01 (10)°] between the benzene rings on either side of this ring indicates a significant fold in this part of the mol-ecule. The dimeth-oxy-substituted benzene ring is almost orthogonal to the benzene ring to which it is attached [dihedral angle = 72.03 (9)°]. The mol-ecule has been observed previously as the major component of a 1:19 co-crystal with 2-amino-4-(3,4-dimeth-oxy-phen-yl)-5,6-dihydro-benzo[ha]quinoline-3-carbonitrile [Asiri et al. (2011). Acta Cryst. E67, o2873-o2873]. Supra-molecular chains with base vector [201] are formed in the crystal structure via N-H⋯O hydrogen bonds between the amino H atoms of one mol-ecule inter-acting with the meth-oxy O atoms of a neighbouring mol-ecule. The chains are linked into a three-dimensional architecture by 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. (2011a ▶,b ▶); n class="Chemical">Al-Youbi et al. (2012 ▶).

Experimental

Crystal data

C24H19N3O2

M = 381.42

Monoclinic,

a = 8.9360 (7) Å

b = 14.5007 (11) Å

c = 14.8074 (11) Å

β = 103.471 (8)°

V = 1865.9 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.20 × 0.15 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.983, T max = 0.991

8105 measured reflections

4272 independent reflections

2851 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.136

S = 1.03

4272 reflections

270 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.23 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: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812011129/sj5212sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812011129/sj5212Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812011129/sj5212Isup3.cml

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

C24H19N3O2	F(000) = 800
Mr = 381.42	Dx = 1.358 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2185 reflections
a = 8.9360 (7) Å	θ = 2.4–27.5°
b = 14.5007 (11) Å	µ = 0.09 mm−1
c = 14.8074 (11) Å	T = 100 K
β = 103.471 (8)°	Chip, orange
V = 1865.9 (2) Å3	0.20 × 0.15 × 0.10 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	4272 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2851 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.037
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.7°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −18→17
Tmin = 0.983, Tmax = 0.991	l = −11→19
8105 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0526P)2 + 0.2552P] where P = (Fo2 + 2Fc2)/3
4272 reflections	(Δ/σ)max = 0.001
270 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.69410 (14)	0.85996 (10)	0.89152 (10)	0.0255 (4)
O2	0.92377 (14)	0.80208 (9)	0.82524 (9)	0.0215 (3)
N1	−0.21440 (18)	0.47271 (12)	0.60427 (12)	0.0271 (4)
N2	−0.0035 (2)	0.62438 (13)	0.51881 (12)	0.0243 (4)
N3	0.31457 (19)	0.75869 (13)	0.50677 (13)	0.0278 (4)
C1	0.1055 (2)	0.47341 (14)	0.82665 (13)	0.0231 (5)
C2	−0.0456 (2)	0.47157 (15)	0.83797 (15)	0.0289 (5)
H2A	−0.1234	0.5058	0.7968	0.035*
C3	−0.0831 (3)	0.42019 (16)	0.90882 (16)	0.0347 (6)
H3	−0.1859	0.4194	0.9160	0.042*
C4	0.0298 (3)	0.37015 (16)	0.96890 (16)	0.0393 (6)
H4	0.0038	0.3338	1.0164	0.047*
C5	0.1807 (3)	0.37300 (15)	0.95975 (15)	0.0350 (6)
H5	0.2576	0.3388	1.0014	0.042*
C6	0.2208 (2)	0.42536 (15)	0.89025 (14)	0.0279 (5)
C7	0.3846 (2)	0.43614 (15)	0.88204 (15)	0.0313 (5)
H7A	0.4029	0.3973	0.8307	0.038*
H7B	0.4561	0.4162	0.9403	0.038*
C8	0.4127 (2)	0.53735 (15)	0.86299 (14)	0.0273 (5)
H8A	0.3967	0.5760	0.9151	0.033*
H8B	0.5200	0.5459	0.8573	0.033*
C9	0.3017 (2)	0.56644 (14)	0.77347 (13)	0.0215 (4)
C10	0.1525 (2)	0.52829 (14)	0.75366 (13)	0.0207 (4)
C11	0.0532 (2)	0.54618 (13)	0.66663 (13)	0.0182 (4)
C12	0.0953 (2)	0.60554 (13)	0.60093 (13)	0.0189 (4)
C13	0.2426 (2)	0.64665 (13)	0.62557 (13)	0.0186 (4)
C14	0.3445 (2)	0.62742 (13)	0.71120 (13)	0.0198 (4)
C15	−0.0950 (2)	0.50286 (14)	0.63642 (14)	0.0221 (4)
C16	0.2857 (2)	0.70935 (14)	0.56101 (14)	0.0210 (4)
C17	0.4968 (2)	0.67539 (14)	0.73596 (13)	0.0199 (4)
C18	0.5213 (2)	0.74481 (14)	0.80346 (14)	0.0215 (5)
H18	0.4402	0.7623	0.8315	0.026*
C19	0.6633 (2)	0.78845 (13)	0.82984 (13)	0.0193 (4)
C20	0.7852 (2)	0.75935 (13)	0.79148 (13)	0.0182 (4)
C21	0.7588 (2)	0.69338 (14)	0.72295 (14)	0.0241 (5)
H21	0.8394	0.6761	0.6944	0.029*
C22	0.6146 (2)	0.65146 (15)	0.69485 (14)	0.0249 (5)
H22	0.5977	0.6062	0.6471	0.030*
C23	0.5626 (2)	0.90343 (16)	0.91355 (16)	0.0333 (6)
H23A	0.5969	0.9532	0.9583	0.050*
H23B	0.5047	0.8578	0.9405	0.050*
H23C	0.4963	0.9289	0.8568	0.050*
C24	1.0509 (2)	0.76905 (15)	0.79032 (15)	0.0257 (5)
H24A	1.1434	0.8047	0.8181	0.039*
H24B	1.0274	0.7762	0.7227	0.039*
H24C	1.0688	0.7038	0.8063	0.039*
H1	−0.105 (3)	0.5996 (17)	0.5047 (17)	0.044 (7)*
H2	0.028 (3)	0.6568 (18)	0.4750 (18)	0.040 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0178 (7)	0.0281 (8)	0.0307 (8)	0.0001 (6)	0.0057 (6)	−0.0119 (7)
O2	0.0141 (6)	0.0248 (8)	0.0260 (7)	−0.0022 (5)	0.0054 (5)	−0.0058 (6)
N1	0.0207 (9)	0.0277 (10)	0.0327 (10)	−0.0014 (7)	0.0060 (7)	0.0010 (8)
N2	0.0186 (9)	0.0298 (11)	0.0222 (9)	−0.0030 (7)	−0.0002 (7)	0.0048 (8)
N3	0.0257 (9)	0.0278 (10)	0.0300 (10)	−0.0031 (7)	0.0065 (8)	0.0015 (9)
C1	0.0304 (11)	0.0185 (11)	0.0196 (10)	−0.0063 (8)	0.0040 (8)	−0.0041 (9)
C2	0.0353 (12)	0.0265 (12)	0.0266 (11)	−0.0058 (9)	0.0111 (9)	−0.0031 (10)
C3	0.0497 (15)	0.0289 (13)	0.0306 (12)	−0.0118 (10)	0.0193 (11)	−0.0060 (10)
C4	0.0641 (17)	0.0315 (14)	0.0255 (12)	−0.0142 (12)	0.0170 (11)	−0.0022 (11)
C5	0.0537 (15)	0.0264 (13)	0.0213 (11)	−0.0054 (11)	0.0016 (10)	0.0002 (10)
C6	0.0400 (13)	0.0228 (12)	0.0179 (10)	−0.0055 (9)	0.0008 (9)	−0.0011 (9)
C7	0.0355 (12)	0.0286 (13)	0.0232 (11)	0.0008 (9)	−0.0063 (9)	0.0025 (10)
C8	0.0278 (11)	0.0302 (12)	0.0203 (10)	−0.0025 (9)	−0.0020 (8)	−0.0014 (10)
C9	0.0222 (10)	0.0198 (11)	0.0200 (10)	0.0011 (8)	−0.0001 (8)	−0.0023 (9)
C10	0.0229 (10)	0.0191 (11)	0.0196 (10)	−0.0005 (8)	0.0038 (8)	−0.0020 (9)
C11	0.0161 (9)	0.0168 (10)	0.0221 (9)	−0.0009 (7)	0.0049 (7)	−0.0037 (8)
C12	0.0163 (9)	0.0192 (10)	0.0202 (9)	0.0017 (7)	0.0025 (7)	−0.0024 (8)
C13	0.0164 (9)	0.0177 (10)	0.0221 (10)	−0.0003 (7)	0.0055 (7)	−0.0015 (8)
C14	0.0163 (9)	0.0206 (10)	0.0223 (10)	0.0021 (8)	0.0036 (8)	−0.0048 (9)
C15	0.0241 (10)	0.0220 (11)	0.0215 (10)	0.0001 (8)	0.0080 (8)	0.0011 (9)
C16	0.0165 (10)	0.0221 (11)	0.0234 (10)	−0.0007 (8)	0.0026 (8)	−0.0029 (9)
C17	0.0155 (9)	0.0217 (10)	0.0206 (10)	0.0007 (8)	0.0001 (7)	0.0006 (9)
C18	0.0152 (9)	0.0264 (11)	0.0229 (10)	0.0026 (8)	0.0042 (8)	−0.0011 (9)
C19	0.0188 (10)	0.0190 (10)	0.0185 (9)	0.0019 (8)	0.0009 (7)	−0.0034 (8)
C20	0.0132 (9)	0.0200 (10)	0.0203 (10)	0.0014 (7)	0.0013 (7)	0.0023 (8)
C21	0.0177 (10)	0.0292 (12)	0.0266 (11)	−0.0009 (8)	0.0078 (8)	−0.0060 (9)
C22	0.0206 (10)	0.0298 (12)	0.0232 (10)	−0.0008 (8)	0.0030 (8)	−0.0078 (9)
C23	0.0241 (11)	0.0366 (14)	0.0410 (13)	0.0009 (9)	0.0109 (9)	−0.0171 (11)
C24	0.0177 (10)	0.0287 (12)	0.0323 (11)	−0.0027 (8)	0.0087 (8)	−0.0074 (10)

O1—C19	1.367 (2)	C8—H8B	0.9900
O1—C23	1.437 (2)	C9—C14	1.394 (3)
O2—C20	1.371 (2)	C9—C10	1.410 (3)
O2—C24	1.436 (2)	C10—C11	1.408 (2)
N1—C15	1.149 (2)	C11—C12	1.414 (3)
N2—C12	1.354 (2)	C11—C15	1.440 (3)
N2—H1	0.95 (2)	C12—C13	1.413 (3)
N2—H2	0.90 (3)	C13—C14	1.406 (2)
N3—C16	1.149 (3)	C13—C16	1.435 (3)
C1—C2	1.400 (3)	C14—C17	1.496 (3)
C1—C6	1.408 (3)	C17—C22	1.377 (3)
C1—C10	1.479 (3)	C17—C18	1.400 (3)
C2—C3	1.390 (3)	C18—C19	1.390 (3)
C2—H2A	0.9500	C18—H18	0.9500
C3—C4	1.384 (3)	C19—C20	1.405 (3)
C3—H3	0.9500	C20—C21	1.374 (3)
C4—C5	1.387 (3)	C21—C22	1.398 (3)
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.391 (3)	C22—H22	0.9500
C5—H5	0.9500	C23—H23A	0.9800
C6—C7	1.504 (3)	C23—H23B	0.9800
C7—C8	1.526 (3)	C23—H23C	0.9800
C7—H7A	0.9900	C24—H24A	0.9800
C7—H7B	0.9900	C24—H24B	0.9800
C8—C9	1.518 (2)	C24—H24C	0.9800
C8—H8A	0.9900
C19—O1—C23	115.90 (15)	C12—C11—C15	115.13 (16)
C20—O2—C24	116.20 (15)	N2—C12—C13	121.33 (19)
C12—N2—H1	120.6 (15)	N2—C12—C11	121.24 (17)
C12—N2—H2	120.2 (15)	C13—C12—C11	117.39 (16)
H1—N2—H2	119 (2)	C14—C13—C12	121.20 (18)
C2—C1—C6	119.1 (2)	C14—C13—C16	120.53 (17)
C2—C1—C10	122.94 (18)	C12—C13—C16	118.26 (16)
C6—C1—C10	117.84 (19)	C9—C14—C13	120.14 (17)
C3—C2—C1	120.6 (2)	C9—C14—C17	120.47 (16)
C3—C2—H2A	119.7	C13—C14—C17	119.35 (18)
C1—C2—H2A	119.7	N1—C15—C11	173.3 (2)
C4—C3—C2	119.9 (2)	N3—C16—C13	177.17 (19)
C4—C3—H3	120.0	C22—C17—C18	119.25 (18)
C2—C3—H3	120.0	C22—C17—C14	121.31 (18)
C3—C4—C5	120.0 (2)	C18—C17—C14	119.43 (18)
C3—C4—H4	120.0	C19—C18—C17	120.58 (19)
C5—C4—H4	120.0	C19—C18—H18	119.7
C4—C5—C6	120.8 (2)	C17—C18—H18	119.7
C4—C5—H5	119.6	O1—C19—C18	124.16 (18)
C6—C5—H5	119.6	O1—C19—C20	116.35 (16)
C5—C6—C1	119.4 (2)	C18—C19—C20	119.49 (18)
C5—C6—C7	122.66 (19)	O2—C20—C21	124.66 (18)
C1—C6—C7	117.94 (19)	O2—C20—C19	115.86 (17)
C6—C7—C8	108.65 (18)	C21—C20—C19	119.47 (17)
C6—C7—H7A	110.0	C20—C21—C22	120.66 (19)
C8—C7—H7A	110.0	C20—C21—H21	119.7
C6—C7—H7B	110.0	C22—C21—H21	119.7
C8—C7—H7B	110.0	C17—C22—C21	120.35 (19)
H7A—C7—H7B	108.3	C17—C22—H22	119.8
C9—C8—C7	109.05 (16)	C21—C22—H22	119.8
C9—C8—H8A	109.9	O1—C23—H23A	109.5
C7—C8—H8A	109.9	O1—C23—H23B	109.5
C9—C8—H8B	109.9	H23A—C23—H23B	109.5
C7—C8—H8B	109.9	O1—C23—H23C	109.5
H8A—C8—H8B	108.3	H23A—C23—H23C	109.5
C14—C9—C10	120.23 (16)	H23B—C23—H23C	109.5
C14—C9—C8	121.98 (17)	O2—C24—H24A	109.5
C10—C9—C8	117.78 (18)	O2—C24—H24B	109.5
C11—C10—C9	118.79 (18)	H24A—C24—H24B	109.5
C11—C10—C1	122.85 (17)	O2—C24—H24C	109.5
C9—C10—C1	118.33 (16)	H24A—C24—H24C	109.5
C10—C11—C12	122.02 (16)	H24B—C24—H24C	109.5
C10—C11—C15	122.79 (18)
C6—C1—C2—C3	−2.5 (3)	C11—C12—C13—C14	1.5 (3)
C10—C1—C2—C3	−178.78 (19)	N2—C12—C13—C16	−0.1 (3)
C1—C2—C3—C4	−0.1 (3)	C11—C12—C13—C16	−178.12 (18)
C2—C3—C4—C5	1.5 (3)	C10—C9—C14—C13	−4.1 (3)
C3—C4—C5—C6	−0.4 (3)	C8—C9—C14—C13	174.73 (19)
C4—C5—C6—C1	−2.2 (3)	C10—C9—C14—C17	173.87 (19)
C4—C5—C6—C7	175.3 (2)	C8—C9—C14—C17	−7.3 (3)
C2—C1—C6—C5	3.6 (3)	C12—C13—C14—C9	0.4 (3)
C10—C1—C6—C5	−179.94 (18)	C16—C13—C14—C9	−179.99 (19)
C2—C1—C6—C7	−174.09 (19)	C12—C13—C14—C17	−177.60 (18)
C10—C1—C6—C7	2.4 (3)	C16—C13—C14—C17	2.0 (3)
C5—C6—C7—C8	−135.7 (2)	C9—C14—C17—C22	107.8 (2)
C1—C6—C7—C8	41.9 (2)	C13—C14—C17—C22	−74.2 (3)
C6—C7—C8—C9	−59.5 (2)	C9—C14—C17—C18	−71.0 (3)
C7—C8—C9—C14	−143.2 (2)	C13—C14—C17—C18	106.9 (2)
C7—C8—C9—C10	35.7 (3)	C22—C17—C18—C19	−0.9 (3)
C14—C9—C10—C11	5.8 (3)	C14—C17—C18—C19	177.97 (18)
C8—C9—C10—C11	−173.11 (18)	C23—O1—C19—C18	−13.7 (3)
C14—C9—C10—C1	−172.40 (19)	C23—O1—C19—C20	165.87 (18)
C8—C9—C10—C1	8.7 (3)	C17—C18—C19—O1	176.45 (17)
C2—C1—C10—C11	−31.5 (3)	C17—C18—C19—C20	−3.1 (3)
C6—C1—C10—C11	152.19 (19)	C24—O2—C20—C21	−5.0 (3)
C2—C1—C10—C9	146.6 (2)	C24—O2—C20—C19	176.54 (17)
C6—C1—C10—C9	−29.7 (3)	O1—C19—C20—O2	4.2 (2)
C9—C10—C11—C12	−3.9 (3)	C18—C19—C20—O2	−176.20 (17)
C1—C10—C11—C12	174.20 (19)	O1—C19—C20—C21	−174.28 (17)
C9—C10—C11—C15	173.50 (19)	C18—C19—C20—C21	5.3 (3)
C1—C10—C11—C15	−8.4 (3)	O2—C20—C21—C22	178.03 (18)
C10—C11—C12—N2	−177.79 (19)	C19—C20—C21—C22	−3.6 (3)
C15—C11—C12—N2	4.6 (3)	C18—C17—C22—C21	2.6 (3)
C10—C11—C12—C13	0.3 (3)	C14—C17—C22—C21	−176.20 (18)
C15—C11—C12—C13	−177.29 (18)	C20—C21—C22—C17	−0.4 (3)
N2—C12—C13—C14	179.56 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1i	0.95 (2)	2.23 (2)	2.921 (2)	129 (2)
N2—H2···O2i	0.90 (3)	2.28 (3)	2.984 (2)	135 (2)
C24—H24B···Cg1ii	0.98	2.78	3.538 (2)	135
C7—H7A···Cg4iii	0.99	2.92	3.792 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C17–C22 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O1i	0.95 (2)	2.23 (2)	2.921 (2)	129 (2)
N2—H2⋯O2i	0.90 (3)	2.28 (3)	2.984 (2)	135 (2)
C24—H24B⋯Cg1ii	0.98	2.78	3.538 (2)	135
C7—H7A⋯Cg4iii	0.99	2.92	3.792 (2)	147

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