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

In the title compound, C(23)H(17)N(3)O, significant deviations from planarity are evidenced. This is quanti-fied in the dihedral angles formed between the central amino-benzene ring and the benzene rings of the meth-oxy-benzene [67.93 (8)°] and 1,2-dihydro-naphthalene [28.27 (8)°] residues. In the crystal the amino-H atoms form hydrogen bonds to the meth-oxy-O atom and to one of the cyano-N atoms to generate a two-dimensional array with a zigzag topology that stacks along the ([Formula: see text][Formula: see text] 1) plane.

Related literature

For background to the biological activity of related compounds, see: Aly et al. (1991 ▶); Al-Saadi et al. (2005 ▶); Rostom et al. (2011 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶). For a related structure, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C23H17N3O

M = 351.40

Monoclinic,

a = 9.0212 (4) Å

b = 22.1475 (8) Å

c = 9.3114 (4) Å

β = 110.410 (5)°

V = 1743.60 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.25 × 0.25 × 0.05 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.714, T max = 1.000

8688 measured reflections

3890 independent reflections

2953 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.116

S = 1.04

3890 reflections

252 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); 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/S1600536811033617/hg5084sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033617/hg5084Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033617/hg5084Isup3.cml

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

C23H17N3O	F(000) = 736
Mr = 351.40	Dx = 1.339 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3338 reflections
a = 9.0212 (4) Å	θ = 2.3–29.3°
b = 22.1475 (8) Å	µ = 0.08 mm−1
c = 9.3114 (4) Å	T = 100 K
β = 110.410 (5)°	Plate, orange
V = 1743.60 (12) Å3	0.25 × 0.25 × 0.05 mm
Z = 4

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	3890 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2953 reflections with I > 2σ(I)
mirror	Rint = 0.030
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.4°
ω scan	h = −9→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −26→28
Tmin = 0.714, Tmax = 1.000	l = −12→11
8688 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0431P)2 + 0.7237P] where P = (Fo2 + 2Fc2)/3
3890 reflections	(Δ/σ)max < 0.001
252 parameters	Δρmax = 0.33 e Å−3
2 restraints	Δρmin = −0.23 e Å−3

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
O1	0.50780 (13)	0.32058 (5)	0.20429 (14)	0.0233 (3)
N1	−0.35267 (17)	−0.04178 (6)	0.09331 (17)	0.0253 (3)
N2	−0.31052 (17)	0.09057 (7)	−0.04975 (18)	0.0273 (4)
H1	−0.341 (2)	0.1248 (6)	−0.101 (2)	0.029 (5)*
H2	−0.383 (2)	0.0640 (8)	−0.048 (2)	0.040 (6)*
N3	−0.12484 (19)	0.22536 (7)	−0.09041 (19)	0.0348 (4)
C1	−0.11308 (18)	0.02880 (7)	0.13513 (19)	0.0181 (3)
C2	−0.15970 (18)	0.08249 (7)	0.04721 (19)	0.0191 (4)
C3	−0.04407 (19)	0.12715 (7)	0.06686 (19)	0.0194 (4)
C4	0.11146 (19)	0.11967 (8)	0.1705 (2)	0.0221 (4)
C5	0.15320 (19)	0.06722 (8)	0.2563 (2)	0.0222 (4)
C6	0.31513 (19)	0.05910 (8)	0.3770 (2)	0.0245 (4)
H6A	0.3719	0.0982	0.3975	0.029*
H6B	0.3777	0.0302	0.3403	0.029*
C7	0.2964 (2)	0.03549 (7)	0.5226 (2)	0.0221 (4)
H7A	0.4017	0.0295	0.6024	0.027*
H7B	0.2372	0.0651	0.5613	0.027*
C8	0.20844 (19)	−0.02353 (7)	0.4888 (2)	0.0201 (4)
C9	0.2469 (2)	−0.07051 (8)	0.5946 (2)	0.0219 (4)
H9	0.3289	−0.0650	0.6908	0.026*
C10	0.1678 (2)	−0.12526 (8)	0.5624 (2)	0.0235 (4)
H10	0.1918	−0.1563	0.6375	0.028*
C11	0.0535 (2)	−0.13428 (8)	0.4195 (2)	0.0242 (4)
H11	0.0014	−0.1722	0.3953	0.029*
C12	0.01471 (19)	−0.08839 (7)	0.3118 (2)	0.0213 (4)
H12	−0.0623	−0.0955	0.2134	0.026*
C13	0.08722 (18)	−0.03175 (7)	0.34554 (19)	0.0182 (3)
C14	0.04050 (18)	0.02098 (7)	0.24062 (19)	0.0183 (3)
C15	−0.24040 (19)	−0.01280 (7)	0.11644 (19)	0.0206 (4)
C16	−0.0873 (2)	0.18193 (8)	−0.0198 (2)	0.0235 (4)
C17	0.22517 (18)	0.17059 (7)	0.18816 (19)	0.0198 (4)
C18	0.20113 (19)	0.22527 (8)	0.25000 (19)	0.0219 (4)
H18	0.1168	0.2292	0.2884	0.026*
C19	0.29915 (19)	0.27411 (8)	0.25614 (19)	0.0200 (4)
H19	0.2823	0.3112	0.2993	0.024*
C20	0.42161 (18)	0.26902 (7)	0.19956 (18)	0.0186 (3)
C21	0.45114 (19)	0.21406 (8)	0.14320 (19)	0.0215 (4)
H21	0.5378	0.2098	0.1084	0.026*
C22	0.35293 (19)	0.16540 (8)	0.13821 (19)	0.0217 (4)
H22	0.3733	0.1277	0.0999	0.026*
C23	0.5989 (2)	0.32247 (8)	0.1054 (2)	0.0254 (4)
H23A	0.6552	0.3611	0.1186	0.038*
H23B	0.5283	0.3184	−0.0013	0.038*
H23C	0.6755	0.2893	0.1314	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0230 (6)	0.0200 (6)	0.0264 (7)	−0.0091 (5)	0.0079 (5)	−0.0019 (5)
N1	0.0189 (7)	0.0213 (8)	0.0318 (8)	−0.0017 (6)	0.0039 (6)	0.0000 (6)
N2	0.0174 (7)	0.0234 (8)	0.0343 (9)	−0.0044 (6)	0.0004 (7)	0.0086 (7)
N3	0.0357 (9)	0.0216 (8)	0.0331 (9)	−0.0061 (7)	−0.0056 (7)	0.0032 (7)
C1	0.0162 (8)	0.0153 (8)	0.0234 (8)	−0.0010 (6)	0.0078 (7)	−0.0013 (6)
C2	0.0171 (8)	0.0200 (8)	0.0202 (8)	−0.0002 (7)	0.0063 (7)	−0.0007 (7)
C3	0.0189 (8)	0.0161 (8)	0.0216 (8)	−0.0005 (6)	0.0052 (7)	0.0010 (6)
C4	0.0192 (8)	0.0194 (9)	0.0263 (9)	−0.0033 (7)	0.0061 (7)	0.0005 (7)
C5	0.0162 (8)	0.0229 (9)	0.0257 (9)	−0.0003 (7)	0.0050 (7)	0.0033 (7)
C6	0.0146 (8)	0.0218 (9)	0.0339 (10)	−0.0008 (7)	0.0043 (7)	0.0060 (8)
C7	0.0179 (8)	0.0183 (8)	0.0268 (9)	0.0009 (7)	0.0036 (7)	0.0005 (7)
C8	0.0170 (8)	0.0184 (8)	0.0268 (9)	0.0033 (7)	0.0101 (7)	0.0003 (7)
C9	0.0205 (8)	0.0222 (9)	0.0235 (9)	0.0052 (7)	0.0083 (7)	0.0009 (7)
C10	0.0245 (9)	0.0181 (9)	0.0306 (10)	0.0049 (7)	0.0130 (8)	0.0060 (7)
C11	0.0198 (8)	0.0162 (8)	0.0377 (10)	0.0015 (7)	0.0114 (8)	0.0026 (7)
C12	0.0156 (8)	0.0200 (9)	0.0278 (9)	0.0017 (7)	0.0071 (7)	0.0006 (7)
C13	0.0140 (7)	0.0153 (8)	0.0266 (9)	0.0034 (6)	0.0090 (7)	0.0023 (7)
C14	0.0173 (8)	0.0164 (8)	0.0224 (8)	0.0014 (6)	0.0083 (7)	0.0004 (7)
C15	0.0194 (8)	0.0186 (8)	0.0220 (9)	0.0039 (7)	0.0049 (7)	0.0016 (7)
C16	0.0193 (8)	0.0200 (9)	0.0251 (9)	−0.0059 (7)	0.0001 (7)	−0.0024 (7)
C17	0.0160 (8)	0.0184 (8)	0.0202 (8)	−0.0019 (7)	0.0002 (7)	0.0034 (7)
C18	0.0174 (8)	0.0254 (9)	0.0214 (9)	−0.0015 (7)	0.0050 (7)	0.0027 (7)
C19	0.0193 (8)	0.0191 (8)	0.0191 (8)	−0.0005 (7)	0.0037 (7)	−0.0025 (7)
C20	0.0166 (8)	0.0189 (8)	0.0165 (8)	−0.0049 (7)	0.0013 (6)	0.0013 (6)
C21	0.0194 (8)	0.0248 (9)	0.0200 (8)	−0.0015 (7)	0.0065 (7)	0.0002 (7)
C22	0.0229 (8)	0.0171 (8)	0.0228 (9)	0.0002 (7)	0.0049 (7)	−0.0011 (7)
C23	0.0219 (9)	0.0271 (10)	0.0261 (9)	−0.0061 (7)	0.0072 (7)	0.0052 (7)

O1—C20	1.3735 (19)	C8—C13	1.411 (2)
O1—C23	1.433 (2)	C9—C10	1.386 (2)
N1—C15	1.154 (2)	C9—H9	0.9500
N2—C2	1.357 (2)	C10—C11	1.384 (2)
N2—H1	0.889 (9)	C10—H10	0.9500
N2—H2	0.883 (9)	C11—C12	1.385 (2)
N3—C16	1.147 (2)	C11—H11	0.9500
C1—C14	1.402 (2)	C12—C13	1.399 (2)
C1—C2	1.421 (2)	C12—H12	0.9500
C1—C15	1.435 (2)	C13—C14	1.486 (2)
C2—C3	1.402 (2)	C17—C22	1.390 (2)
C3—C4	1.408 (2)	C17—C18	1.390 (2)
C3—C16	1.434 (2)	C18—C19	1.385 (2)
C4—C5	1.385 (2)	C18—H18	0.9500
C4—C17	1.494 (2)	C19—C20	1.384 (2)
C5—C14	1.414 (2)	C19—H19	0.9500
C5—C6	1.512 (2)	C20—C21	1.388 (2)
C6—C7	1.517 (2)	C21—C22	1.386 (2)
C6—H6A	0.9900	C21—H21	0.9500
C6—H6B	0.9900	C22—H22	0.9500
C7—C8	1.504 (2)	C23—H23A	0.9800
C7—H7A	0.9900	C23—H23B	0.9800
C7—H7B	0.9900	C23—H23C	0.9800
C8—C9	1.391 (2)
C20—O1—C23	116.67 (13)	C9—C10—H10	120.3
C2—N2—H1	121.6 (13)	C10—C11—C12	120.38 (16)
C2—N2—H2	118.4 (14)	C10—C11—H11	119.8
H1—N2—H2	119.1 (19)	C12—C11—H11	119.8
C14—C1—C2	121.91 (14)	C11—C12—C13	121.00 (16)
C14—C1—C15	124.01 (15)	C11—C12—H12	119.5
C2—C1—C15	113.81 (14)	C13—C12—H12	119.5
N2—C2—C3	121.41 (15)	C12—C13—C8	118.40 (15)
N2—C2—C1	121.35 (15)	C12—C13—C14	123.62 (15)
C3—C2—C1	117.23 (14)	C8—C13—C14	117.96 (14)
C2—C3—C4	121.63 (15)	C1—C14—C5	118.82 (15)
C2—C3—C16	118.66 (15)	C1—C14—C13	122.83 (14)
C4—C3—C16	119.70 (15)	C5—C14—C13	118.19 (14)
C5—C4—C3	119.95 (15)	N1—C15—C1	173.19 (17)
C5—C4—C17	122.08 (15)	N3—C16—C3	178.65 (19)
C3—C4—C17	117.93 (15)	C22—C17—C18	118.55 (15)
C4—C5—C14	120.44 (15)	C22—C17—C4	121.21 (15)
C4—C5—C6	121.76 (15)	C18—C17—C4	120.19 (15)
C14—C5—C6	117.65 (15)	C19—C18—C17	120.51 (15)
C5—C6—C7	109.01 (14)	C19—C18—H18	119.7
C5—C6—H6A	109.9	C17—C18—H18	119.7
C7—C6—H6A	109.9	C20—C19—C18	120.22 (15)
C5—C6—H6B	109.9	C20—C19—H19	119.9
C7—C6—H6B	109.9	C18—C19—H19	119.9
H6A—C6—H6B	108.3	O1—C20—C19	115.98 (14)
C8—C7—C6	109.13 (14)	O1—C20—C21	124.07 (15)
C8—C7—H7A	109.9	C19—C20—C21	119.94 (15)
C6—C7—H7A	109.9	C22—C21—C20	119.35 (15)
C8—C7—H7B	109.9	C22—C21—H21	120.3
C6—C7—H7B	109.9	C20—C21—H21	120.3
H7A—C7—H7B	108.3	C21—C22—C17	121.31 (15)
C9—C8—C13	119.53 (15)	C21—C22—H22	119.3
C9—C8—C7	121.24 (15)	C17—C22—H22	119.3
C13—C8—C7	119.21 (15)	O1—C23—H23A	109.5
C10—C9—C8	121.23 (16)	O1—C23—H23B	109.5
C10—C9—H9	119.4	H23A—C23—H23B	109.5
C8—C9—H9	119.4	O1—C23—H23C	109.5
C11—C10—C9	119.31 (16)	H23A—C23—H23C	109.5
C11—C10—H10	120.3	H23B—C23—H23C	109.5
C14—C1—C2—N2	−177.16 (16)	C9—C8—C13—C14	175.09 (14)
C15—C1—C2—N2	−3.0 (2)	C7—C8—C13—C14	−6.4 (2)
C14—C1—C2—C3	1.8 (2)	C2—C1—C14—C5	−1.9 (2)
C15—C1—C2—C3	175.94 (15)	C15—C1—C14—C5	−175.51 (15)
N2—C2—C3—C4	178.21 (17)	C2—C1—C14—C13	173.29 (15)
C1—C2—C3—C4	−0.7 (2)	C15—C1—C14—C13	−0.3 (3)
N2—C2—C3—C16	−0.9 (3)	C4—C5—C14—C1	1.0 (2)
C1—C2—C3—C16	−179.86 (15)	C6—C5—C14—C1	176.69 (15)
C2—C3—C4—C5	−0.1 (3)	C4—C5—C14—C13	−174.42 (16)
C16—C3—C4—C5	179.01 (16)	C6—C5—C14—C13	1.3 (2)
C2—C3—C4—C17	−177.76 (15)	C12—C13—C14—C1	28.1 (2)
C16—C3—C4—C17	1.4 (2)	C8—C13—C14—C1	−150.04 (16)
C3—C4—C5—C14	0.0 (3)	C12—C13—C14—C5	−156.66 (16)
C17—C4—C5—C14	177.51 (16)	C8—C13—C14—C5	25.2 (2)
C3—C4—C5—C6	−175.50 (16)	C5—C4—C17—C22	70.5 (2)
C17—C4—C5—C6	2.0 (3)	C3—C4—C17—C22	−111.93 (18)
C4—C5—C6—C7	132.25 (17)	C5—C4—C17—C18	−112.04 (19)
C14—C5—C6—C7	−43.4 (2)	C3—C4—C17—C18	65.5 (2)
C5—C6—C7—C8	58.90 (18)	C22—C17—C18—C19	2.4 (2)
C6—C7—C8—C9	142.75 (15)	C4—C17—C18—C19	−175.12 (15)
C6—C7—C8—C13	−35.7 (2)	C17—C18—C19—C20	0.5 (2)
C13—C8—C9—C10	−0.3 (2)	C23—O1—C20—C19	−160.73 (14)
C7—C8—C9—C10	−178.80 (15)	C23—O1—C20—C21	19.5 (2)
C8—C9—C10—C11	3.0 (2)	C18—C19—C20—O1	177.14 (14)
C9—C10—C11—C12	−2.2 (2)	C18—C19—C20—C21	−3.1 (2)
C10—C11—C12—C13	−1.4 (2)	O1—C20—C21—C22	−177.48 (15)
C11—C12—C13—C8	4.0 (2)	C19—C20—C21—C22	2.8 (2)
C11—C12—C13—C14	−174.11 (15)	C20—C21—C22—C17	0.2 (2)
C9—C8—C13—C12	−3.2 (2)	C18—C17—C22—C21	−2.7 (2)
C7—C8—C13—C12	175.35 (15)	C4—C17—C22—C21	174.76 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1i	0.89 (1)	2.21 (1)	3.0307 (19)	154.(2)
N2—H2···N1ii	0.88 (1)	2.33 (1)	3.115 (2)	149.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O1i	0.89 (1)	2.21 (1)	3.0307 (19)	154 (2)
N2—H2⋯N1ii	0.88 (1)	2.33 (1)	3.115 (2)	149 (2)

Symmetry codes: (i) ; (ii) .