3-Amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile

Asiri, A.M.; Faidallah, H.M.; Alamry, K.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812011129

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o1118-o1119

doi:10.1107/S1600536812011129

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3-Amino-1-(3,4-dimethoxyphenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile

Abdullah M. Asiri,^a,^b ‡ Hassan M. Faidallah,^a Khalid A. Alamry,^a Seik Weng Ng ^c,^a 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, Jeddah, PO Box 80203, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 13 March 2012; accepted 14 March 2012; online 21 March 2012)

In the title compound, C₂₄H₁₉N₃O₂, the partially saturated ring adopts a distorted half-chair conformation with the methylene-C atom closest to the aminobenzene 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 molecule. The dimethoxy-substituted benzene ring is almost orthogonal to the benzene ring to which it is attached [dihedral angle = 72.03 (9)°]. The molecule has been observed previously as the major component of a 1:19 co-crystal with 2-amino-4-(3,4-dimethoxyphenyl)-5,6-dihydrobenzo[ha]quinoline-3-carbonitrile [Asiri et al. (2011). Acta Cryst. E67, o2873–o2873]. Supramolecular chains with base vector [201] are formed in the crystal structure via N—H⋯O hydrogen bonds between the amino H atoms of one molecule interacting with the methoxy O atoms of a neighbouring molecule. The chains are linked into a three-dimensional architecture by C—H⋯π interactions.

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 ); Al-Youbi et al. (2012 ).

Experimental

Crystal data

C₂₄H₁₉N₃O₂
M_r = 381.42
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.055
wR(F²) = 0.136
S = 1.03
4272 reflections
270 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 e Å⁻³

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) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812011129/sj5212sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812011129/sj5212Isup3.cml

checkCIF report

Comment top

The X-ray crystallographic investigation of the title compound, 3-amino-1-(3,4-dimethoxyphenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile (I), was motivated by reports of the biological activity of related compounds (Wang et al., 2010; Rostom et al., 2011) and allied crystal structure investigations (Asiri et al., 2011a; Al-Youbi et al., 2012). The molecule of (I) has been observed previously in its 1/19 co-crystal with 2-amino-4-(3,4-dimethoxyphenyl)-5,6-dihydrobenzo[ha]quinoline-3-carbonitrile (Asiri et al., 2011b).

In (I), Fig. 1, the partially saturated ring adopts a distorted twisted half chair conformation with the C2 atom lying 0.664 (3) Å out of the plane defined by the five remaining atoms [r.m.s. deviation = 0.1429 Å; maximum deviations = 0.1733 (11) Å for the C9 atom and -0.2097 (14) Å for the C10 atom]. The dihedral angle between the benzene rings on either side of this ring = 32.01 (10)°, indicating a significant fold in this part of the molecule. The dimethoxy-substituted benzene ring is almost normal to the plane of the benzene ring to which it is attached, forming a dihedral angle of 72.03 (9)° The O1-and O2-methoxy substituents are each slightly twisted out of the plane of the benzene ring to which they are attached as seen in the values of the C23—O1—C19—C18 and C24—O2—C20—C21 torsion angles of -13.7 (3) and -5.0 (3)°, respectively; they lie to opposite sides of the plane through the benzene ting.

The most prominent feature in the crystal packing is the formation of N—H···O hydrogen bonds whereby the amino-H atoms are connected to the two methoxy-O atoms of a neighbouring molecule leading to a seven-membered {···HNH···OC₂O} synthon linked into twisted supramolecular chains, Fig. 2 and Table 1; the base vector is along [2 0 1]. Clearly, the presence of two oxygen atoms in (I), is sufficient to disrupt the normally formed N—H···N hydrogen bonds between centrosymmetrically related molecules leading to to 12-membered {···HNC₃N}₂ synthons (Asiri et al., 2011a; Asiri et al., 2011b). Supramolecular chains are sustained in a three-dimensional architecture by C—H···π interactions, Fig. 3 and Table 1.

Related literature top

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); Al-Youbi et al. (2012).

Experimental top

A mixture of 3,4-dimethoxybenzaldehyde (1.66 g, 0.01 mmol), 1-tetralone (1.46 g, 0.01 mmol), malononitrile (0.66 g, 0.01 mmol) and ammonium acetate (6.2 g, 0.08 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The reaction mixture was allowed to cool. The precipitate that formed was filtered, washed with water, dried and recrystallized from ethanol. Yield: 69%, M. pt. 533–535 K.

Structure description top

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); Al-Youbi et al. (2012).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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. The supramolecular chain in (I) sustained by N—H···O hydrogen bonds shown as blue dashed lines.
	Fig. 3. A view in projection down the a axis of the unit-cell contents of (I). The N—H···O hydrogen bonds and C—H···π interactions are shown as blue and purple dashed lines, respectively.

3-Amino-1-(3,4-dimethoxyphenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile top

Crystal data top

C₂₄H₁₉N₃O₂	F(000) = 800
M_r = 381.42	D_x = 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

Data collection top

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	R_int = 0.037
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.7°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −18→17
T_min = 0.983, T_max = 0.991	l = −11→19
8105 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)] = 0.055	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(F_o²) + (0.0526P)² + 0.2552P] where P = (F_o² + 2F_c²)/3
4272 reflections	(Δ/σ)_max = 0.001
270 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₄H₁₉N₃O₂	V = 1865.9 (2) Å³
M_r = 381.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9360 (7) Å	µ = 0.09 mm⁻¹
b = 14.5007 (11) Å	T = 100 K
c = 14.8074 (11) Å	0.20 × 0.15 × 0.10 mm
β = 103.471 (8)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4272 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2851 reflections with I > 2σ(I)
T_min = 0.983, T_max = 0.991	R_int = 0.037
8105 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.25 e Å⁻³
4272 reflections	Δρ_min = −0.23 e Å⁻³
270 parameters

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₄H₁₉N₃O₂
M_r	381.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.9360 (7), 14.5007 (11), 14.8074 (11)
β (°)	103.471 (8)
V (Å³)	1865.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.983, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	8105, 4272, 2851
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.136, 1.03
No. of reflections	4272
No. of parameters	270
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.23

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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

Footnotes

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

Acknowledgements

The authors are grateful to the Center of Excellence for Advanced Materials Research and the Chemistry Department at King Abdulaziz University for providing the research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Al-Youbi, A. O., Asiri, A. M., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o1027–o1028. CSD CrossRef IUCr Journals Google Scholar
Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M. & Ng, S. W. (2011b). Acta Cryst. E67, o2873. Web of Science CSD CrossRef IUCr Journals Google Scholar
Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2011a). Acta Cryst. E67, o2449. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. 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. 20, 1260–1272. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, K., Hu, Y., Liu, Y., Mi, N., Fan, Z., Liu, Y. & Wang, Q. (2010). J. Agric. Food Chem. 58, 12337–12342. Web of Science CrossRef CAS PubMed Google Scholar
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Volume 68| Part 4| April 2012| Pages o1118-o1119

doi:10.1107/S1600536812011129

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

3-Amino-1-(3,4-dimeth­­oxy­phen­yl)-9,10-di­hydro­phenanthrene-2,4-dicarbo­nitrile

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

3-Amino-1-(3,4-dimethoxyphenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile