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

Asiri, A.M.; Al-Youbi, A.O.; Faidallah, H.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811033563

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2438

doi:10.1107/S1600536811033563

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

Abdullah M. Asiri,^a,^b ‡ Abdulrahman O. Al-Youbi,^a Hassan M. Faidallah,^a Seik Weng Ng ^c and Edward R. T. Tiekink ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, ^bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 16 August 2011; accepted 17 August 2011; online 27 August 2011)

In the title compound, C₂₃H₁₅N₃O₂, 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-dihydronaphthalene [26.27 (14)°] residues; the dioxole ring has an envelope conformation with the methylene-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 ( $[\overline{1}]$ 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_r = 365.38
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.065
wR(F²) = 0.167
S = 1.02
3775 reflections
261 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.30 e Å⁻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) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+3, -y+1, -z+2.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033563/om2463sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811033563/om2463Isup3.cml

checkCIF report

Comment top

The study of the title compound (I) was motivated by recent reports of the biological activity of related compounds (Aly et al., 1991; Al-Saadi et al., 2005; Rostom et al., 2011).

With respect to the amino-benzene ring, the benzene rings of the 1,3-benzodioxole and 1,2-dihydronaphthalene residues form dihedral angles of 65.38 (12) and 26.27 (14) °, respectively, indicating non-planarity in the molecule. The five-membered dioxole ring has an envelope conformation with the methylene-C23 atom being the flap atom. The Cremer & Pople (1975) parameters defining the five-membered ring are q₂ = 0.182 (3) Å and ϕ₂ = 324.8 (9) Å. In the 1,2-dihydronaphthalene residue, the cyclohexa-1,3-diene ring has a distorted half-chair conformation as defined by the following parameters (Cremer & Pople, 1975): q₂ = 0.503 (3) Å, ϕ₂ = 265.5 (3) °, q₃ = -0.189 (3) Å, and puckering amplitude Q = 0.537 (3) Å.

In the crystal structure, supramolecular arrays with zigzag topology and running parallel to the (1 0 2) plane are formed through N—H···O(dioxole) and N—H···N(cyano) hydrogen bonding Table 1 and Fig. 2.

Related literature top

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 top

A mixture of the piperonaldehyde (1.5 g,10 mmol), 1-tetralone (1.46 g, 10 mmol), ethyl cyanoacetate (1.1 g, 10 mmol) and ammonium acetate (6.2 g, 80 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool and the precipitate that formed was filtered, washed with water, dried and recrystallized from DMF; M.pt.: 549–551 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular array in (I) viewed towards the (1 0 2) plane. The N—H···O and N—H···.N hydrogen bonds are shown as orange and blue dashed lines, respectively.

3-Amino-1-(2H-1,3-benzodioxol-5-yl)-9,10-dihydrophenanthrene-2,4- dicarbonitrile top

Crystal data top

C₂₃H₁₅N₃O₂	F(000) = 760
M_r = 365.38	D_x = 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

Data collection top

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 monochromator	R_int = 0.042
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
ω scan	h = −9→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −29→24
T_min = 0.776, T_max = 1.000	l = −11→11
9604 measured reflections

Refinement top

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(F_o²) + (0.0527P)² + 2.2435P] where P = (F_o² + 2F_c²)/3
3775 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.65 e Å⁻³
2 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₃H₁₅N₃O₂	V = 1695.18 (19) Å³
M_r = 365.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9280 (6) Å	µ = 0.09 mm⁻¹
b = 22.4518 (13) Å	T = 100 K
c = 8.9473 (6) Å	0.25 × 0.25 × 0.05 mm
β = 109.058 (7)°

Data collection top

Agilent Technologies SuperNova Dual diffractometer with Atlas detector	3775 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2570 reflections with I > 2σ(I)
T_min = 0.776, T_max = 1.000	R_int = 0.042
9604 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	2 restraints
wR(F²) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.65 e Å⁻³
3775 reflections	Δρ_min = −0.30 e Å⁻³
261 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, −y+1/2, z+1/2; (ii) −x+3, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₅N₃O₂
M_r	365.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.9280 (6), 22.4518 (13), 8.9473 (6)
β (°)	109.058 (7)
V (Å³)	1695.18 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.25 × 0.05

Data collection
Diffractometer	Agilent Technologies SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.776, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9604, 3775, 2570
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.167, 1.02
No. of reflections	3775
No. of parameters	261
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.30

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1ⁱ	0.883 (10)	2.400 (17)	3.231 (3)	157 (3)
N2—H2···N1ⁱⁱ	0.877 (10)	2.369 (17)	3.188 (3)	156 (3)

Symmetry codes: (i) x+1, −y+1/2, z+1/2; (ii) −x+3, −y+1, −z+2.

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors thank King Abdulaziz University and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Al-Saadi, S. M., Rostom, S. A. F. & Faid Allah, H. M. (2005). Alexandria J. Pharm. Sci. 19, 15–21. CAS Google Scholar
Aly, A. S., El-Ezabawy, S. R. & Abdel-Fattah, A. M. (1991). Egypt. J. Pharm. Sci. 32, 827–834. CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Rostom, S. A. F., Faidallah, S. M. & Al Saadi, M. S. (2011). Med. Chem. Res. DOI: 10.1007/s00044-010-9469-0. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 9| September 2011| Page o2438

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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