3-Amino-1-(2H-1,3-benzodioxol-5-yl)-9,10-dihydro-phenanthrene-2,4-dicarbonitrile.

In the title compound, C(23)H(15)N(3)O(2), significant deviations from planarity are evidenced in the values of the dihedral angles formed between the amino-benzene ring and the benzene rings of the 1,3-benzodioxole [65.38 (12)°] and 1,2-dihydro-naphthalene [26.27 (14)°] residues; the dioxole ring has an envelope conformation with the methyl-ene-C being the flap atom. The amino-H atoms form hydrogen bonds to one of the dioxole-O atoms 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] 0 2) 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 ▶).

Experimental

Crystal data

C23H15N3O2

M = 365.38

Monoclinic,

a = 8.9280 (6) Å

b = 22.4518 (13) Å

c = 8.9473 (6) Å

β = 109.058 (7)°

V = 1695.18 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.09 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 = 0.776, T max = 1.000

9604 measured reflections

3775 independent reflections

2570 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.167

S = 1.02

3775 reflections

261 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.65 e Å−3

Δρmin = −0.30 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/S1600536811033563/om2463sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033563/om2463Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033563/om2463Isup3.cml

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

C23H15N3O2	F(000) = 760
Mr = 365.38	Dx = 1.432 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2779 reflections
a = 8.9280 (6) Å	θ = 2.4–29.3°
b = 22.4518 (13) Å	µ = 0.09 mm−1
c = 8.9473 (6) Å	T = 100 K
β = 109.058 (7)°	Plate, orange
V = 1695.18 (19) Å3	0.25 × 0.25 × 0.05 mm
Z = 4

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	3775 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2570 reflections with I > 2σ(I)
mirror	Rint = 0.042
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.6°
ω scan	h = −9→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −29→24
Tmin = 0.776, Tmax = 1.000	l = −11→11
9604 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0527P)2 + 2.2435P] where P = (Fo2 + 2Fc2)/3
3775 reflections	(Δ/σ)max < 0.001
261 parameters	Δρmax = 0.65 e Å−3
2 restraints	Δρmin = −0.30 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	0.4763 (2)	0.18869 (9)	0.8357 (2)	0.0314 (5)
O2	0.4316 (2)	0.28084 (9)	0.9262 (2)	0.0331 (5)
N1	1.3481 (3)	0.53871 (11)	0.9128 (3)	0.0338 (6)
N2	1.3145 (3)	0.40625 (12)	1.0585 (3)	0.0336 (6)
H1	1.344 (4)	0.3728 (9)	1.112 (4)	0.052 (11)*
H2	1.389 (3)	0.4315 (12)	1.058 (4)	0.046 (10)*
N3	1.1365 (3)	0.27041 (11)	1.0990 (3)	0.0334 (6)
C1	0.8958 (3)	0.37338 (12)	0.8347 (3)	0.0258 (6)
C2	0.8496 (3)	0.42563 (13)	0.7482 (3)	0.0272 (6)
C3	0.6849 (3)	0.43271 (14)	0.6300 (4)	0.0342 (7)
H3A	0.6205	0.4587	0.6746	0.041*
H3B	0.6323	0.3934	0.6065	0.041*
C4	0.6975 (3)	0.46015 (13)	0.4790 (3)	0.0306 (7)
H4A	0.7561	0.4329	0.4310	0.037*
H4B	0.5902	0.4663	0.4021	0.037*
C5	0.7827 (3)	0.51885 (12)	0.5167 (3)	0.0270 (6)
C6	0.7385 (3)	0.56661 (13)	0.4116 (4)	0.0297 (6)
H6	0.6541	0.5618	0.3148	0.036*
C7	0.8153 (3)	0.62062 (13)	0.4460 (4)	0.0343 (7)
H7	0.7874	0.6523	0.3717	0.041*
C8	0.9328 (4)	0.62819 (13)	0.5890 (4)	0.0360 (7)
H8	0.9838	0.6657	0.6145	0.043*
C9	0.9777 (3)	0.58157 (13)	0.6968 (4)	0.0312 (7)
H9	1.0571	0.5879	0.7962	0.037*
C10	0.9068 (3)	0.52541 (12)	0.6600 (3)	0.0263 (6)
C11	0.9590 (3)	0.47229 (12)	0.7635 (3)	0.0261 (6)
C12	1.1138 (3)	0.46557 (12)	0.8686 (3)	0.0240 (6)
C13	1.1643 (3)	0.41274 (12)	0.9576 (3)	0.0259 (6)
C14	1.0515 (3)	0.36702 (12)	0.9370 (3)	0.0243 (6)
C15	1.2379 (3)	0.50862 (12)	0.8885 (3)	0.0268 (6)
C16	1.0980 (3)	0.31309 (13)	1.0264 (3)	0.0271 (6)
C17	0.7828 (3)	0.32335 (13)	0.8240 (3)	0.0260 (6)
C18	0.8070 (3)	0.26822 (13)	0.7666 (3)	0.0304 (6)
H18	0.8925	0.2635	0.7265	0.037*
C19	0.7098 (3)	0.21922 (14)	0.7657 (3)	0.0315 (7)
H19	0.7270	0.1814	0.7264	0.038*
C20	0.5905 (3)	0.22874 (13)	0.8238 (3)	0.0274 (6)
C21	0.5615 (3)	0.28346 (13)	0.8782 (3)	0.0273 (6)
C22	0.6548 (3)	0.33250 (13)	0.8791 (3)	0.0278 (6)
H22	0.6335	0.3703	0.9151	0.033*
C23	0.3996 (4)	0.21835 (13)	0.9305 (4)	0.0326 (7)
H23A	0.4403	0.2035	1.0405	0.039*
H23B	0.2840	0.2110	0.8889	0.039*

	U11	U22	U33	U12	U13	U23
O1	0.0306 (11)	0.0281 (11)	0.0333 (11)	−0.0128 (9)	0.0074 (8)	−0.0032 (9)
O2	0.0300 (11)	0.0322 (12)	0.0402 (12)	−0.0058 (9)	0.0157 (9)	−0.0018 (9)
N1	0.0301 (13)	0.0236 (13)	0.0451 (15)	−0.0017 (11)	0.0086 (11)	0.0032 (11)
N2	0.0231 (12)	0.0274 (15)	0.0453 (15)	−0.0042 (11)	0.0046 (11)	0.0105 (12)
N3	0.0318 (13)	0.0273 (14)	0.0369 (14)	−0.0058 (11)	0.0051 (11)	0.0039 (12)
C1	0.0254 (14)	0.0258 (15)	0.0292 (14)	−0.0026 (11)	0.0131 (11)	0.0030 (12)
C2	0.0226 (13)	0.0283 (16)	0.0325 (15)	−0.0007 (11)	0.0115 (11)	0.0044 (12)
C3	0.0238 (14)	0.0345 (18)	0.0443 (18)	−0.0021 (13)	0.0112 (13)	0.0090 (14)
C4	0.0269 (14)	0.0267 (16)	0.0378 (16)	−0.0010 (12)	0.0100 (12)	0.0064 (13)
C5	0.0237 (14)	0.0248 (15)	0.0378 (16)	0.0040 (11)	0.0171 (12)	0.0048 (12)
C6	0.0289 (15)	0.0259 (16)	0.0384 (16)	0.0069 (12)	0.0166 (12)	0.0063 (13)
C7	0.0349 (16)	0.0234 (16)	0.0483 (19)	0.0092 (13)	0.0187 (14)	0.0068 (14)
C8	0.0350 (16)	0.0185 (15)	0.057 (2)	0.0030 (12)	0.0178 (15)	0.0002 (14)
C9	0.0273 (14)	0.0246 (16)	0.0434 (17)	0.0053 (12)	0.0141 (13)	0.0003 (13)
C10	0.0219 (13)	0.0221 (15)	0.0397 (16)	0.0035 (11)	0.0165 (12)	0.0021 (12)
C11	0.0257 (14)	0.0245 (15)	0.0313 (15)	0.0018 (11)	0.0134 (11)	0.0017 (12)
C12	0.0232 (13)	0.0193 (14)	0.0339 (15)	−0.0005 (11)	0.0151 (11)	−0.0012 (12)
C13	0.0256 (14)	0.0218 (15)	0.0317 (15)	−0.0014 (11)	0.0112 (11)	0.0008 (12)
C14	0.0252 (14)	0.0209 (14)	0.0288 (14)	−0.0014 (11)	0.0114 (11)	0.0024 (11)
C15	0.0271 (14)	0.0217 (15)	0.0317 (15)	0.0023 (12)	0.0096 (11)	0.0023 (12)
C16	0.0211 (13)	0.0292 (16)	0.0306 (15)	−0.0066 (12)	0.0081 (11)	−0.0009 (13)
C17	0.0257 (14)	0.0275 (15)	0.0240 (14)	−0.0042 (12)	0.0071 (11)	0.0043 (12)
C18	0.0275 (14)	0.0352 (17)	0.0271 (15)	−0.0003 (13)	0.0070 (11)	0.0019 (13)
C19	0.0290 (15)	0.0331 (17)	0.0272 (15)	0.0010 (13)	0.0022 (12)	−0.0021 (13)
C20	0.0294 (14)	0.0259 (15)	0.0210 (13)	−0.0054 (12)	0.0002 (11)	0.0015 (11)
C21	0.0251 (14)	0.0363 (17)	0.0213 (13)	−0.0030 (12)	0.0088 (11)	0.0035 (12)
C22	0.0315 (15)	0.0250 (15)	0.0279 (14)	−0.0057 (12)	0.0109 (11)	−0.0025 (12)
C23	0.0349 (16)	0.0278 (17)	0.0344 (16)	−0.0083 (13)	0.0104 (13)	0.0011 (13)

O1—C20	1.389 (3)	C7—C8	1.374 (4)
O1—C23	1.418 (3)	C7—H7	0.9500
O2—C21	1.364 (3)	C8—C9	1.391 (4)
O2—C23	1.435 (3)	C8—H8	0.9500
N1—C15	1.154 (4)	C9—C10	1.401 (4)
N2—C13	1.358 (4)	C9—H9	0.9500
N2—H1	0.883 (10)	C10—C11	1.488 (4)
N2—H2	0.877 (10)	C11—C12	1.403 (4)
N3—C16	1.145 (4)	C12—C13	1.418 (4)
C1—C2	1.392 (4)	C12—C15	1.437 (4)
C1—C14	1.400 (4)	C13—C14	1.407 (4)
C1—C17	1.492 (4)	C14—C16	1.436 (4)
C2—C11	1.409 (4)	C17—C18	1.384 (4)
C2—C3	1.513 (4)	C17—C22	1.399 (4)
C3—C4	1.522 (4)	C18—C19	1.400 (4)
C3—H3A	0.9900	C18—H18	0.9500
C3—H3B	0.9900	C19—C20	1.346 (4)
C4—C5	1.504 (4)	C19—H19	0.9500
C4—H4A	0.9900	C20—C21	1.376 (4)
C4—H4B	0.9900	C21—C22	1.379 (4)
C5—C6	1.396 (4)	C22—H22	0.9500
C5—C10	1.402 (4)	C23—H23A	0.9900
C6—C7	1.378 (4)	C23—H23B	0.9900
C6—H6	0.9500
C20—O1—C23	104.5 (2)	C5—C10—C11	118.6 (2)
C21—O2—C23	104.3 (2)	C12—C11—C2	119.0 (2)
C13—N2—H1	120 (2)	C12—C11—C10	122.9 (2)
C13—N2—H2	121 (2)	C2—C11—C10	118.0 (2)
H1—N2—H2	117 (3)	C11—C12—C13	122.0 (2)
C2—C1—C14	120.1 (2)	C11—C12—C15	124.2 (2)
C2—C1—C17	121.8 (2)	C13—C12—C15	113.7 (2)
C14—C1—C17	118.1 (2)	N2—C13—C14	121.2 (3)
C1—C2—C11	120.2 (3)	N2—C13—C12	121.8 (2)
C1—C2—C3	121.4 (2)	C14—C13—C12	117.0 (2)
C11—C2—C3	118.3 (2)	C1—C14—C13	121.8 (3)
C2—C3—C4	109.1 (2)	C1—C14—C16	119.7 (2)
C2—C3—H3A	109.9	C13—C14—C16	118.5 (2)
C4—C3—H3A	109.9	N1—C15—C12	173.0 (3)
C2—C3—H3B	109.9	N3—C16—C14	179.2 (3)
C4—C3—H3B	109.9	C18—C17—C22	120.4 (3)
H3A—C3—H3B	108.3	C18—C17—C1	120.9 (2)
C5—C4—C3	109.5 (2)	C22—C17—C1	118.7 (3)
C5—C4—H4A	109.8	C17—C18—C19	122.3 (3)
C3—C4—H4A	109.8	C17—C18—H18	118.9
C5—C4—H4B	109.8	C19—C18—H18	118.9
C3—C4—H4B	109.8	C20—C19—C18	116.1 (3)
H4A—C4—H4B	108.2	C20—C19—H19	121.9
C6—C5—C10	120.1 (3)	C18—C19—H19	121.9
C6—C5—C4	120.7 (3)	C19—C20—C21	122.8 (3)
C10—C5—C4	119.2 (2)	C19—C20—O1	128.3 (3)
C7—C6—C5	121.0 (3)	C21—C20—O1	108.9 (2)
C7—C6—H6	119.5	O2—C21—C20	110.5 (2)
C5—C6—H6	119.5	O2—C21—C22	127.4 (3)
C8—C7—C6	119.3 (3)	C20—C21—C22	122.1 (2)
C8—C7—H7	120.3	C21—C22—C17	116.2 (3)
C6—C7—H7	120.3	C21—C22—H22	121.9
C7—C8—C9	120.8 (3)	C17—C22—H22	121.9
C7—C8—H8	119.6	O1—C23—O2	107.7 (2)
C9—C8—H8	119.6	O1—C23—H23A	110.2
C8—C9—C10	120.6 (3)	O2—C23—H23A	110.2
C8—C9—H9	119.7	O1—C23—H23B	110.2
C10—C9—H9	119.7	O2—C23—H23B	110.2
C9—C10—C5	118.1 (3)	H23A—C23—H23B	108.5
C9—C10—C11	123.3 (3)
C14—C1—C2—C11	−0.1 (4)	C11—C12—C13—C14	−0.5 (4)
C17—C1—C2—C11	178.9 (2)	C15—C12—C13—C14	−176.4 (2)
C14—C1—C2—C3	176.7 (3)	C2—C1—C14—C13	0.9 (4)
C17—C1—C2—C3	−4.3 (4)	C17—C1—C14—C13	−178.1 (2)
C1—C2—C3—C4	−135.0 (3)	C2—C1—C14—C16	179.7 (3)
C11—C2—C3—C4	41.8 (4)	C17—C1—C14—C16	0.7 (4)
C2—C3—C4—C5	−57.5 (3)	N2—C13—C14—C1	179.3 (3)
C3—C4—C5—C6	−143.6 (3)	C12—C13—C14—C1	−0.6 (4)
C3—C4—C5—C10	35.8 (3)	N2—C13—C14—C16	0.5 (4)
C10—C5—C6—C7	0.1 (4)	C12—C13—C14—C16	−179.4 (2)
C4—C5—C6—C7	179.5 (2)	C2—C1—C17—C18	117.0 (3)
C5—C6—C7—C8	−2.8 (4)	C14—C1—C17—C18	−64.0 (4)
C6—C7—C8—C9	1.9 (4)	C2—C1—C17—C22	−65.5 (4)
C7—C8—C9—C10	1.7 (4)	C14—C1—C17—C22	113.5 (3)
C8—C9—C10—C5	−4.2 (4)	C22—C17—C18—C19	−2.1 (4)
C8—C9—C10—C11	174.4 (3)	C1—C17—C18—C19	175.3 (3)
C6—C5—C10—C9	3.4 (4)	C17—C18—C19—C20	0.1 (4)
C4—C5—C10—C9	−176.1 (2)	C18—C19—C20—C21	1.5 (4)
C6—C5—C10—C11	−175.3 (2)	C18—C19—C20—O1	179.3 (2)
C4—C5—C10—C11	5.2 (4)	C23—O1—C20—C19	169.6 (3)
C1—C2—C11—C12	−1.0 (4)	C23—O1—C20—C21	−12.3 (3)
C3—C2—C11—C12	−177.8 (3)	C23—O2—C21—C20	11.9 (3)
C1—C2—C11—C10	175.7 (2)	C23—O2—C21—C22	−168.8 (3)
C3—C2—C11—C10	−1.1 (4)	C19—C20—C21—O2	178.4 (2)
C9—C10—C11—C12	−26.2 (4)	O1—C20—C21—O2	0.2 (3)
C5—C10—C11—C12	152.4 (3)	C19—C20—C21—C22	−1.0 (4)
C9—C10—C11—C2	157.2 (3)	O1—C20—C21—C22	−179.2 (2)
C5—C10—C11—C2	−24.2 (4)	O2—C21—C22—C17	179.7 (3)
C2—C11—C12—C13	1.3 (4)	C20—C21—C22—C17	−1.0 (4)
C10—C11—C12—C13	−175.2 (2)	C18—C17—C22—C21	2.5 (4)
C2—C11—C12—C15	176.7 (3)	C1—C17—C22—C21	−174.9 (2)
C10—C11—C12—C15	0.2 (4)	C20—O1—C23—O2	19.6 (3)
C11—C12—C13—N2	179.6 (3)	C21—O2—C23—O1	−19.5 (3)
C15—C12—C13—N2	3.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1i	0.88 (1)	2.40 (2)	3.231 (3)	157 (3)
N2—H2···N1ii	0.88 (1)	2.37 (2)	3.188 (3)	156 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O1i	0.88 (1)	2.40 (2)	3.231 (3)	157 (3)
N2—H2⋯N1ii	0.88 (1)	2.37 (2)	3.188 (3)	156 (3)

Symmetry codes: (i) ; (ii) .