2-Amino-4-phenyl-5,6-dihydro­benzo[h]quinoline-3-carbonitrile–3-amino-1-phenyl-9,10-dihydro­phenanthrene-2,4-dicarbonitrile (5/3)

Asiri, A.M.; Al-Youbi, A.O.; Faidallah, H.M.; Ng, S.W.

doi:10.1107/S1600536811040505

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2872

doi:10.1107/S1600536811040505

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2-Amino-4-phenyl-5,6-dihydrobenzo[h]quinoline-3-carbonitrile–3-amino-1-phenyl-9,10-dihydrophenanthrene-2,4-dicarbonitrile (5/3)

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

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia, ^bCenter 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: seikweng@um.edu.my

(Received 11 September 2011; accepted 3 October 2011; online 8 October 2011)

The asymmetric unit of the 5:3 title co-crystal of 2-amino-4-phenyl-5,6-dihydrobenzo[h]quinoline-3-carbonitrile and 3-amino-1-phenyl-9,10-dihydrophenanthrene-2,4-dicarbonitrile, 0.625C₂₀H₁₅N₃.0.375C₂₂H₁₅N₃, has the atoms of the fused-ring system and those of the amino, cyano and phenyl substitutents overlapped. The fused-ring system is buckled owing to the ethylene linkage in the central ring, the two flanking aromatic rings being twisted by 20.1 (1)°. This ethylene portion is disordered over two positions in a 1:1 ratio. The phenyl ring is twisted by 69.5 (1)° relative to the amino- and cyano-bearing aromatic ring. In the crystal, two molecules are linked by an N—H⋯N hydrogen bond, generating a a helical chain along [010].

Related literature

For the synthesis, see: Aly et al. (1991 ); Paul et al. (1998 ). For related structures, see: Asiri et al. (2011a ,b ).

Experimental

Crystal data

0.625C₂₀H₁₅N₃·0.375C₂₂H₁₅N₃
M_r = 306.36
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.9611 (2) Å
b = 12.6093 (2) Å
c = 17.4933 (3) Å
V = 1535.47 (6) Å³
Z = 4
Cu Kα radiation
μ = 0.62 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.835, T_max = 0.988
6293 measured reflections
1794 independent reflections
1707 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.119
S = 1.05
1794 reflections
240 parameters
24 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯N3ⁱ	0.88 (1)	2.37 (2)	3.175 (2)	152 (3)
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z+{\script{5\over 2}}]$ .

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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811040505/zs2145sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040505/zs2145Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811040505/zs2145Isup3.cml

checkCIF report

Comment top

2-Amino-4-phenyl-5,6-dihydrobenzoquinoline-3-carbonitrile is synthesized from the reaction of the α-substituted cinnamonitrile, C₆H₅CH═C(CN)₂, with α-tetralone in a reaction that is catalyzed by ammonium acetate (Aly et al., 1991). The synthesis when conducted under microwave irradiation leads to an improved yield (Paul et al., 1998). In previous studies, we obtained instead di-carbonitrile substituted dihydrophenanthrenes (3-amino-1-(4-methoxyphenyl)-9,10- dihydrophenanthrene-2,4-dicarbonitrile and 3-amino-1-(2H-1,3-benzodioxol-5-yl)- 9,10-dihydrophenanthrene-2,4-dicarbonitrile) with 4-methoxybenzaldehyde and piperonaldehyde in syntheses that differed slightly from the reported ones as we used substituted benzaldehydes, α-tetralone and ethyl cyanoacetate along with a molar excess of ammonium acetate (Asiri et al., 2011a; 2011b).

In this study, the reaction of benzaldehyde, α-tetralone and ethyl cyanoacetate yielded the co-crystal of 2-amino-4-phenyl-5,6-dihydrobenzoquinoline-3-carbonitrile (C₂₀H₁₅N₃) and 3-amino-1-phenyl-9,10-dihydrophenanthrene-2,4-dicarbonitrile (C₂₂H₁₅N₃), with the two components present in a 5: 3 molar ratio (Scheme I). The fused-ring system is buckled owing to the ethylene linkage in the central ring with the two flanking aromatic rings twisted by 20.1 (1)°. Relative to the amino- and cyano-bearing aromatic ring, the phenyl ring is twisted by 69.5 (1) ° (Fig. 1 and Fig. 2). Two molecules are linked by an N—H···N hydrogen bond to generate a helical chain (Table 1 and Fig. 3). The ethylene portion is disordered over two positions in a 1:1 ratio.

Related literature top

For the synthesis, see: Aly et al. (1991); Paul et al. (1998). For related structures, see: Asiri et al. (2011a,b).

Experimental top

A mixture of benzaldehyde (1.06 g,10 mmol), α-tetralone (1.46 g, 10 mmol), ethyl cyanoacetate (1.13 g, 10 mmol) and ammonium acetate (6.16 g, 80 mmol) in absolute ethanol (50 ml) was refluxed for 6 h. The mixture was allowed to cool and the precipitate that formed was filtered, washed with water, dried and recrystallized from DMF.

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₂₀H₁₅N₃ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Thermal ellipsoid plot (Barbour, 2001) of C₂₂H₁₅N₃ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 3. Thermal ellipsoid plot (Barbour, 2001) of C₂₀H₁₅N₃ (62.5% component) and C₂₂H₁₅N₃ (37.5% component) related by twofold screw axial symmetry. For symmetry code (i), see Table 1.

2-Amino-4-phenyl-5,6-dihydrobenzo[h]quinoline-3-carbonitrile– 3-amino-1-phenyl-9,10-dihydrophenanthrene-2,4-dicarbonitrile (5/3) top

Crystal data top

0.625C₂₀H₁₅N₃·0.375C₂₂H₁₅N₃	F(000) = 642
M_r = 306.36	D_x = 1.325 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3717 reflections
a = 6.9611 (2) Å	θ = 3.5–74.3°
b = 12.6093 (2) Å	µ = 0.62 mm⁻¹
c = 17.4933 (3) Å	T = 100 K
V = 1535.47 (6) Å³	Plate, brown-orange
Z = 4	0.30 × 0.20 × 0.02 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	1794 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1707 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.018
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.5°, θ_min = 4.3°
ω scans	h = −8→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→15
T_min = 0.835, T_max = 0.988	l = −21→20
6293 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0796P)² + 0.2871P] where P = (F_o² + 2F_c²)/3
1794 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.19 e Å⁻³
24 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

0.625C₂₀H₁₅N₃·0.375C₂₂H₁₅N₃	V = 1535.47 (6) Å³
M_r = 306.36	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 6.9611 (2) Å	µ = 0.62 mm⁻¹
b = 12.6093 (2) Å	T = 100 K
c = 17.4933 (3) Å	0.30 × 0.20 × 0.02 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	1794 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	1707 reflections with I > 2σ(I)
T_min = 0.835, T_max = 0.988	R_int = 0.018
6293 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	24 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.19 e Å⁻³
1794 reflections	Δρ_min = −0.23 e Å⁻³
240 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.9898 (3)	0.26050 (14)	1.05516 (10)	0.0294 (4)	0.625
C1'	0.9898 (3)	0.26050 (14)	1.05516 (10)	0.0294 (4)	0.375
N2	1.0082 (3)	0.28041 (13)	1.18789 (10)	0.0339 (4)
H1	1.035 (5)	0.3483 (10)	1.1827 (17)	0.052 (8)*
H2	1.031 (4)	0.254 (2)	1.2335 (9)	0.045 (8)*
N3	0.9475 (4)	0.02407 (14)	1.26992 (10)	0.0396 (5)
C1	0.9186 (4)	−0.07603 (16)	1.08021 (11)	0.0369 (5)
C2	1.0684 (4)	−0.13801 (17)	1.10772 (12)	0.0414 (6)
H2A	1.1883	−0.1063	1.1200	0.050*
C3	1.0422 (5)	−0.24706 (17)	1.11721 (12)	0.0463 (7)
H3	1.1450	−0.2896	1.1355	0.056*
C4	0.8687 (5)	−0.29307 (17)	1.10017 (12)	0.0500 (8)
H4	0.8513	−0.3671	1.1075	0.060*
C5	0.7187 (5)	−0.23191 (18)	1.07229 (14)	0.0521 (7)
H5	0.5990	−0.2641	1.0603	0.063*
C6	0.7439 (5)	−0.12301 (18)	1.06183 (13)	0.0478 (6)
H6	0.6418	−0.0811	1.0422	0.057*
C7	0.9453 (4)	0.04111 (15)	1.06991 (11)	0.0336 (5)
C8	0.9536 (4)	0.08663 (16)	0.99730 (11)	0.0391 (6)
C9	0.9790 (10)	0.0170 (5)	0.9251 (4)	0.0390 (15)	0.50
H9A	1.0343	−0.0525	0.9396	0.047*	0.50
H9B	0.8524	0.0043	0.9010	0.047*	0.50
C10	1.1119 (9)	0.0727 (5)	0.8684 (3)	0.0440 (15)	0.50
H10A	1.1216	0.0310	0.8206	0.053*	0.50
H10B	1.2422	0.0801	0.8905	0.053*	0.50
C9'	0.9024 (9)	0.0270 (5)	0.9245 (4)	0.0390 (15)	0.50
H9'C	0.9220	−0.0500	0.9322	0.047*	0.50
H9'D	0.7656	0.0390	0.9117	0.047*	0.50
C10'	1.0290 (10)	0.0659 (5)	0.8592 (3)	0.0440 (15)	0.50
H10C	1.1628	0.0426	0.8683	0.053*	0.50
H10D	0.9847	0.0335	0.8108	0.053*	0.50
C11	1.0247 (5)	0.18419 (19)	0.85163 (13)	0.0485 (7)
C12	1.0305 (5)	0.2290 (2)	0.77912 (15)	0.0561 (7)
H12	1.0608	0.1859	0.7362	0.067*
C13	0.9929 (5)	0.3351 (3)	0.76887 (17)	0.0606 (8)
H13	0.9963	0.3651	0.7191	0.073*
C14	0.9497 (5)	0.3981 (3)	0.8318 (2)	0.0699 (10)
H14	0.9246	0.4716	0.8250	0.084*
C15	0.9431 (5)	0.3542 (2)	0.90409 (18)	0.0593 (9)
H15	0.9134	0.3976	0.9469	0.071*
C16	0.9798 (4)	0.24669 (16)	0.91469 (12)	0.0355 (5)
C17	0.9738 (3)	0.19760 (15)	0.99194 (12)	0.0331 (5)
C18	0.9871 (3)	0.21628 (14)	1.12653 (11)	0.0281 (4)
C19	0.9622 (3)	0.10550 (15)	1.13457 (11)	0.0291 (4)
C20	0.9531 (4)	0.05995 (15)	1.20987 (11)	0.0308 (5)
N4	1.0072 (11)	0.4629 (4)	1.0526 (3)	0.0471 (15)	0.375
C21	0.9965 (10)	0.3721 (4)	1.0492 (3)	0.0337 (12)	0.375

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0427 (10)	0.0207 (8)	0.0249 (8)	0.0010 (8)	0.0045 (8)	0.0015 (7)
C1'	0.0427 (10)	0.0207 (8)	0.0249 (8)	0.0010 (8)	0.0045 (8)	0.0015 (7)
N2	0.0607 (12)	0.0210 (7)	0.0200 (7)	−0.0002 (9)	−0.0011 (8)	−0.0010 (6)
N3	0.0672 (14)	0.0253 (8)	0.0263 (8)	0.0000 (9)	−0.0015 (9)	0.0044 (7)
C1	0.0703 (16)	0.0214 (9)	0.0189 (8)	−0.0041 (10)	−0.0016 (10)	0.0008 (7)
C2	0.0705 (16)	0.0260 (10)	0.0277 (9)	0.0011 (11)	−0.0012 (11)	−0.0002 (8)
C3	0.087 (2)	0.0257 (10)	0.0259 (10)	0.0058 (12)	0.0027 (12)	0.0009 (8)
C4	0.106 (2)	0.0201 (9)	0.0239 (10)	−0.0060 (13)	0.0035 (12)	0.0016 (8)
C5	0.089 (2)	0.0300 (10)	0.0370 (12)	−0.0174 (13)	−0.0096 (13)	0.0029 (10)
C6	0.0785 (18)	0.0283 (10)	0.0365 (11)	−0.0092 (12)	−0.0159 (13)	0.0053 (9)
C7	0.0539 (13)	0.0211 (9)	0.0258 (9)	−0.0025 (9)	−0.0007 (10)	0.0002 (8)
C8	0.0704 (16)	0.0228 (9)	0.0241 (9)	−0.0043 (11)	−0.0002 (11)	0.0017 (8)
C9	0.069 (4)	0.0245 (14)	0.0237 (10)	0.001 (3)	−0.002 (3)	0.0004 (10)
C10	0.082 (5)	0.0283 (13)	0.0211 (15)	−0.013 (3)	−0.001 (2)	−0.0071 (11)
C9'	0.069 (4)	0.0245 (14)	0.0237 (10)	0.001 (3)	−0.002 (3)	0.0004 (10)
C10'	0.082 (5)	0.0283 (13)	0.0211 (15)	−0.013 (3)	−0.001 (2)	−0.0071 (11)
C11	0.0804 (19)	0.0357 (11)	0.0293 (11)	−0.0080 (14)	0.0008 (12)	0.0083 (9)
C12	0.080 (2)	0.0562 (15)	0.0321 (12)	−0.0134 (16)	0.0003 (13)	0.0126 (11)
C13	0.0538 (14)	0.0720 (19)	0.0559 (16)	0.0019 (16)	0.0020 (14)	0.0404 (15)
C14	0.0675 (19)	0.0549 (16)	0.087 (2)	0.0299 (16)	0.0384 (18)	0.0452 (16)
C15	0.0674 (18)	0.0408 (13)	0.0698 (18)	0.0201 (14)	0.0372 (16)	0.0274 (13)
C16	0.0429 (11)	0.0291 (10)	0.0347 (11)	0.0004 (10)	0.0053 (9)	0.0096 (9)
C17	0.0456 (11)	0.0240 (9)	0.0297 (10)	0.0003 (10)	0.0041 (10)	0.0026 (8)
C18	0.0405 (11)	0.0215 (8)	0.0224 (9)	0.0005 (9)	0.0001 (8)	−0.0002 (7)
C19	0.0432 (11)	0.0224 (9)	0.0218 (9)	−0.0005 (9)	0.0001 (9)	0.0028 (7)
C20	0.0480 (12)	0.0195 (8)	0.0249 (9)	−0.0013 (9)	−0.0017 (9)	−0.0011 (7)
N4	0.094 (5)	0.021 (2)	0.026 (2)	−0.002 (3)	0.001 (3)	−0.0014 (18)
C21	0.055 (3)	0.027 (3)	0.018 (2)	0.003 (3)	0.005 (2)	−0.0001 (19)

Geometric parameters (Å, º) top

N1—C17	1.366 (3)	C9—H9B	0.9900
N1—C18	1.367 (2)	C10—C11	1.560 (7)
N2—C18	1.352 (2)	C10—H10A	0.9900
N2—H1	0.88 (1)	C10—H10B	0.9900
N2—H2	0.88 (1)	C9'—C10'	1.523 (7)
N3—C20	1.144 (3)	C9'—H9'C	0.9900
C1—C6	1.391 (4)	C9'—H9'D	0.9900
C1—C2	1.389 (4)	C10'—C11	1.498 (7)
C1—C7	1.499 (3)	C10'—H10C	0.9900
C2—C3	1.397 (3)	C10'—H10D	0.9900
C2—H2A	0.9500	C11—C12	1.389 (3)
C3—C4	1.373 (4)	C11—C16	1.391 (3)
C3—H3	0.9500	C12—C13	1.375 (4)
C4—C5	1.387 (4)	C12—H12	0.9500
C4—H4	0.9500	C13—C14	1.390 (5)
C5—C6	1.396 (3)	C13—H13	0.9500
C5—H5	0.9500	C14—C15	1.382 (4)
C6—H6	0.9500	C14—H14	0.9500
C7—C19	1.397 (3)	C15—C16	1.392 (3)
C7—C8	1.395 (3)	C15—H15	0.9500
C8—C17	1.410 (3)	C16—C17	1.487 (3)
C8—C9'	1.521 (7)	C18—C19	1.415 (2)
C8—C9	1.548 (7)	C19—C20	1.438 (3)
C9—C10	1.527 (7)	N4—C21	1.149 (7)
C9—H9A	0.9900

C17—N1—C18	120.11 (16)	C10'—C9'—C8	109.5 (4)
C18—N2—H1	122 (2)	C10'—C9'—H9'C	109.8
C18—N2—H2	120.8 (19)	C8—C9'—H9'C	109.8
H1—N2—H2	115 (3)	C10'—C9'—H9'D	109.8
C6—C1—C2	119.8 (2)	C8—C9'—H9'D	109.8
C6—C1—C7	120.0 (2)	H9'C—C9'—H9'D	108.2
C2—C1—C7	120.2 (2)	C11—C10'—C9'	112.1 (5)
C1—C2—C3	119.8 (3)	C11—C10'—H10C	109.2
C1—C2—H2A	120.1	C9'—C10'—H10C	109.2
C3—C2—H2A	120.1	C11—C10'—H10D	109.2
C4—C3—C2	120.3 (3)	C9'—C10'—H10D	109.2
C4—C3—H3	119.8	H10C—C10'—H10D	107.9
C2—C3—H3	119.8	C12—C11—C16	120.0 (2)
C3—C4—C5	120.2 (2)	C12—C11—C10'	119.0 (3)
C3—C4—H4	119.9	C16—C11—C10'	119.9 (3)
C5—C4—H4	119.9	C12—C11—C10	121.8 (3)
C4—C5—C6	119.9 (3)	C16—C11—C10	116.7 (3)
C4—C5—H5	120.0	C13—C12—C11	120.6 (3)
C6—C5—H5	120.0	C13—C12—H12	119.7
C1—C6—C5	119.9 (3)	C11—C12—H12	119.7
C1—C6—H6	120.1	C12—C13—C14	119.6 (2)
C5—C6—H6	120.1	C12—C13—H13	120.2
C19—C7—C8	119.64 (17)	C14—C13—H13	120.2
C19—C7—C1	119.05 (17)	C15—C14—C13	120.1 (3)
C8—C7—C1	121.31 (17)	C15—C14—H14	119.9
C7—C8—C17	118.24 (18)	C13—C14—H14	119.9
C7—C8—C9'	123.3 (3)	C14—C15—C16	120.4 (3)
C17—C8—C9'	117.3 (3)	C14—C15—H15	119.8
C7—C8—C9	120.9 (3)	C16—C15—H15	119.8
C17—C8—C9	119.8 (3)	C15—C16—C11	119.2 (2)
C10—C9—C8	109.7 (5)	C15—C16—C17	121.4 (2)
C10—C9—H9A	109.7	C11—C16—C17	119.40 (18)
C8—C9—H9A	109.7	N1—C17—C8	122.06 (18)
C10—C9—H9B	109.7	N1—C17—C16	119.48 (18)
C8—C9—H9B	109.7	C8—C17—C16	118.46 (18)
H9A—C9—H9B	108.2	N2—C18—N1	118.65 (16)
C9—C10—C11	107.5 (5)	N2—C18—C19	121.67 (16)
C9—C10—H10A	110.2	N1—C18—C19	119.68 (17)
C11—C10—H10A	110.2	C7—C19—C18	120.24 (17)
C9—C10—H10B	110.2	C7—C19—C20	120.37 (17)
C11—C10—H10B	110.2	C18—C19—C20	119.39 (17)
H10A—C10—H10B	108.5	N3—C20—C19	179.3 (3)

C6—C1—C2—C3	−0.4 (3)	C10—C11—C12—C13	−165.4 (4)
C7—C1—C2—C3	179.9 (2)	C11—C12—C13—C14	0.4 (5)
C1—C2—C3—C4	−0.6 (3)	C12—C13—C14—C15	−0.5 (5)
C2—C3—C4—C5	1.0 (4)	C13—C14—C15—C16	0.1 (5)
C3—C4—C5—C6	−0.3 (4)	C14—C15—C16—C11	0.5 (5)
C2—C1—C6—C5	1.1 (4)	C14—C15—C16—C17	179.9 (3)
C7—C1—C6—C5	−179.3 (2)	C12—C11—C16—C15	−0.7 (5)
C4—C5—C6—C1	−0.7 (4)	C10'—C11—C16—C15	−168.7 (4)
C6—C1—C7—C19	110.6 (3)	C10—C11—C16—C15	165.6 (3)
C2—C1—C7—C19	−69.8 (3)	C12—C11—C16—C17	179.9 (3)
C6—C1—C7—C8	−69.5 (3)	C10'—C11—C16—C17	11.8 (5)
C2—C1—C7—C8	110.1 (3)	C10—C11—C16—C17	−13.8 (4)
C19—C7—C8—C17	−1.7 (4)	C18—N1—C17—C8	0.2 (4)
C1—C7—C8—C17	178.4 (2)	C18—N1—C17—C16	−179.2 (2)
C19—C7—C8—C9'	−169.0 (4)	C7—C8—C17—N1	1.5 (4)
C1—C7—C8—C9'	11.0 (5)	C9'—C8—C17—N1	169.6 (3)
C19—C7—C8—C9	166.8 (4)	C9—C8—C17—N1	−167.1 (4)
C1—C7—C8—C9	−13.1 (5)	C7—C8—C17—C16	−179.1 (2)
C7—C8—C9—C10	−141.5 (4)	C9'—C8—C17—C16	−11.0 (4)
C17—C8—C9—C10	26.9 (6)	C9—C8—C17—C16	12.3 (5)
C9'—C8—C9—C10	115.4 (13)	C15—C16—C17—N1	−19.7 (4)
C8—C9—C10—C11	−55.9 (6)	C11—C16—C17—N1	159.7 (2)
C7—C8—C9'—C10'	−146.4 (4)	C15—C16—C17—C8	160.9 (3)
C17—C8—C9'—C10'	46.2 (6)	C11—C16—C17—C8	−19.7 (4)
C9—C8—C9'—C10'	−56.5 (11)	C17—N1—C18—N2	178.3 (2)
C8—C9'—C10'—C11	−52.0 (6)	C17—N1—C18—C19	−1.8 (3)
C9'—C10'—C11—C12	−143.3 (4)	C8—C7—C19—C18	0.2 (4)
C9'—C10'—C11—C16	24.9 (6)	C1—C7—C19—C18	−179.9 (2)
C9'—C10'—C11—C10	113.0 (11)	C8—C7—C19—C20	179.7 (2)
C9—C10—C11—C12	−142.0 (4)	C1—C7—C19—C20	−0.4 (3)
C9—C10—C11—C16	51.9 (5)	N2—C18—C19—C7	−178.5 (2)
C9—C10—C11—C10'	−52.2 (9)	N1—C18—C19—C7	1.6 (3)
C16—C11—C12—C13	0.2 (5)	N2—C18—C19—C20	2.0 (4)
C10'—C11—C12—C13	168.4 (4)	N1—C18—C19—C20	−177.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N3ⁱ	0.88 (1)	2.37 (2)	3.175 (2)	152 (3)

Symmetry code: (i) −x+2, y+1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula	0.625C₂₀H₁₅N₃·0.375C₂₂H₁₅N₃
M_r	306.36
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	6.9611 (2), 12.6093 (2), 17.4933 (3)
V (Å³)	1535.47 (6)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.62
Crystal size (mm)	0.30 × 0.20 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.835, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	6293, 1794, 1707
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.119, 1.05
No. of reflections	1794
No. of parameters	240
No. of restraints	24
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.23

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···N3ⁱ	0.88 (1)	2.37 (2)	3.175 (2)	152 (3)

Symmetry code: (i) −x+2, y+1/2, −z+5/2.

Acknowledgements

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

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Aly, A. S., El-Ezabawy, S. R. & Abdel-Fattah, A. M. (1991). Egypt. J. Pharm. Sci. 32, 827–834. CAS Google Scholar
Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2011a). Acta Cryst. E67, o2438. 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. (2011b). Acta Cryst. E67, o2449. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Paul, S., Gupta, R. & Loupy, A. (1998). J. Chem. Res. (S), pp. 330–331. Web of Science CrossRef 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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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Amino-4-phenyl-5,6-di­hydro­benzo[h]quinoline-3-carbo­nitrile–3-amino-1-phenyl-9,10-di­hydro­phenanthrene-2,4-dicarbo­nitrile (5/3)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Amino-4-phenyl-5,6-dihydrobenzo[h]quinoline-3-carbonitrile–3-amino-1-phenyl-9,10-dihydrophenanthrene-2,4-dicarbonitrile (5/3)