2-Amino-4-(3,4-dimeth­oxy­phen­yl)-5,6-dihydro­benzo[h]quinoline-3-carbo­nitrile–3-amino-1-(3,4-dimeth­oxy­phen­yl)-9,10-dihydro­phenanthrene-2,4-dicarbonitrile (1/19)

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

doi:10.1107/S1600536811040517

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2873

doi:10.1107/S1600536811040517

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2-Amino-4-(3,4-dimethoxyphenyl)-5,6-dihydrobenzo[h]quinoline-3-carbonitrile–3-amino-1-(3,4-dimethoxyphenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile (1/19)

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 1:19 title co-crystal of 2-amino-4-(3,4-dimethoxyphenyl)-5,6-dihydrobenzo[h]quinoline-3-carbonitrile and 3-amino-1-(3,4-dimethoxyphenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile, 0.05C₂₂H₁₉N₃O₂·0.95C₂₄H₁₉N₃O₂, has the atoms of the fused-ring system and those of the amino, cyano and dimethoxyphenyl substitutents overlapped. The fused-ring system is buckled owing to the ethylene linkage in the central ring with the two flanking aromatic rings being twisted by 31.9 (1)°. The ring of the dimethoxyphenyl substituent is twisted by 72.4 (1)° relative to the amino- and cyano-bearing aromatic ring. In the crystal, molecules are linked by duplex amine N—H⋯O(methoxy) hydrogen bonds in a cyclic association [graph-set R₂²(7)], generating a helical chain structure extending along [201].

Related literature

For a similar co-crystal, see: Asiri et al. (2011 ). For graph-set analysis, see: Etter et al. (1990 ).

Experimental

Crystal data

0.05C₂₂H₁₉N₃O₂·0.95C₂₄H₁₉N₃O₂
M_r = 380.22
Monoclinic, P 2₁ /c
a = 8.9347 (3) Å
b = 14.4915 (5) Å
c = 14.7818 (6) Å
β = 103.446 (4)°
V = 1861.45 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.974, T_max = 0.983
9240 measured reflections
4160 independent reflections
3146 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.124
S = 1.04
4160 reflections
270 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O1ⁱ	0.95 (2)	2.24 (2)	2.927 (2)	129 (2)
N3—H2⋯O2ⁱ	0.92 (2)	2.25 (2)	2.987 (2)	136 (2)
Symmetry code: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536811040517/zs2146sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040517/zs2146Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811040517/zs2146Isup3.cml

checkCIF report

Comment top

2-Amino-5,6-dihydro-4-phenyl-benzoquinoline-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. The synthesis when conducted under microwave irradiation leads to an improved yield. 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.

In this study, the reaction of 3,4-dimethoxybenzaldehyde, α-tetralone and ethyl cyanoacetate yielded the co-crystal of 2-amino-4-(3,4-dimethoxyphenyl)-5,6-dihydrobenzoquinoline-3-carbonitrile (C₂₂H₁₉N₃O₂) and 3-amino-1-(3,4-dimethoxyphenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile (C₂₄H₁₉N₃O₂) with the components present in a 1: 19 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 31.9 (1) °. Relative to the amino- and cyano-bearing aromatic ring, the benzene ring is twisted by 72.4 (1) ° (Figs. 1 and 2). Molecules are linked by duplex amine N–H···O (methoxy) hydrogen bonds (Table 1) in a cyclic association [graph set R²₂(7) (Etter et al., 1990)], generating a helical chain structure extending along [2 0 1].

Related literature top

For a similar co-crystal, see: Asiri et al. (2011). For graph-set analysis, see: Etter et al. (1990).

Experimental top

A mixture of 3,4-dimethoxybenzaldehyde (1.66 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 C₂₂H₁₉N₃O₂ (molecule 1) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Thermal ellipsoid plot (Barbour, 2001) of C₂₄H₁₉N₃O₂ (molecule 2) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

2-Amino-4-(3,4-dimethoxyphenyl)-5,6-dihydrobenzo[h]quinoline-3- carbonitrile–3-amino-1-(3,4-dimethoxyphenyl)-9,10-dihydrophenanthrene-2,4- dicarbonitrile (1/19) top

Crystal data top

0.05C₂₂H₁₉N₃O₂·0.95C₂₄H₁₉N₃O₂	F(000) = 797.6
M_r = 380.22	D_x = 1.357 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3220 reflections
a = 8.9347 (3) Å	θ = 2.3–29.2°
b = 14.4915 (5) Å	µ = 0.09 mm⁻¹
c = 14.7818 (6) Å	T = 100 K
β = 103.446 (4)°	Block, orange
V = 1861.45 (12) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4160 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3146 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.3°
ω scans	h = −11→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −18→17
T_min = 0.974, T_max = 0.983	l = −19→17
9240 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0502P)² + 0.6446P] where P = (F_o² + 2F_c²)/3
4160 reflections	(Δ/σ)_max = 0.001
270 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

0.05C₂₂H₁₉N₃O₂·0.95C₂₄H₁₉N₃O₂	V = 1861.45 (12) Å³
M_r = 380.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9347 (3) Å	µ = 0.09 mm⁻¹
b = 14.4915 (5) Å	T = 100 K
c = 14.7818 (6) Å	0.30 × 0.25 × 0.20 mm
β = 103.446 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4160 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3146 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.983	R_int = 0.031
9240 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.30 e Å⁻³
4160 reflections	Δρ_min = −0.24 e Å⁻³
270 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.30588 (13)	0.63995 (9)	0.10804 (8)	0.0271 (3)
O2	0.07648 (12)	0.69798 (8)	0.17421 (8)	0.0220 (3)
N1	0.94620 (18)	0.95400 (11)	0.33260 (11)	0.0197 (3)	0.05
C1'	0.94620 (18)	0.95400 (11)	0.33260 (11)	0.0197 (3)	0.95
N2	1.21403 (18)	1.02734 (11)	0.39566 (11)	0.0279 (4)	0.95
N3	1.00292 (18)	0.87635 (11)	0.48043 (11)	0.0271 (4)
H1	1.104 (3)	0.9012 (16)	0.4948 (16)	0.053 (7)*
H2	0.973 (2)	0.8423 (15)	0.5258 (15)	0.035 (6)*
N4	0.68515 (17)	0.74165 (11)	0.49326 (11)	0.0294 (4)
C1	0.84721 (19)	0.97189 (11)	0.24628 (11)	0.0209 (4)
C2	0.8945 (2)	1.02681 (12)	0.17292 (12)	0.0253 (4)
C3	1.0457 (2)	1.02878 (13)	0.16227 (13)	0.0315 (4)
H3	1.1232	0.9947	0.2038	0.038*
C4	1.0837 (3)	1.07998 (14)	0.09164 (14)	0.0374 (5)
H4	1.1867	1.0808	0.0847	0.045*
C5	0.9711 (3)	1.12980 (14)	0.03145 (14)	0.0425 (5)
H5	0.9976	1.1660	−0.0161	0.051*
C6	0.8200 (3)	1.12739 (13)	0.03999 (13)	0.0382 (5)
H6	0.7435	1.1618	−0.0019	0.046*
C7	0.7794 (2)	1.07502 (12)	0.10951 (12)	0.0295 (4)
C8	0.6159 (2)	1.06430 (13)	0.11720 (13)	0.0326 (4)
H8A	0.5449	1.0839	0.0585	0.039*
H8B	0.5970	1.1035	0.1682	0.039*
C9	0.5876 (2)	0.96303 (13)	0.13680 (12)	0.0292 (4)
H9A	0.4801	0.9547	0.1424	0.035*
H9B	0.6036	0.9242	0.0848	0.035*
C10	0.69749 (19)	0.93394 (12)	0.22619 (12)	0.0231 (4)
C11	0.65552 (18)	0.87253 (11)	0.28827 (11)	0.0213 (4)
C12	0.75689 (18)	0.85343 (11)	0.37374 (11)	0.0193 (3)
C13	0.90408 (18)	0.89474 (11)	0.39830 (11)	0.0196 (3)
C14	1.0941 (2)	0.99715 (12)	0.36327 (12)	0.0225 (4)	0.95
C15	0.71436 (18)	0.79079 (12)	0.43878 (12)	0.0224 (4)
C16	0.50312 (18)	0.82492 (12)	0.26343 (11)	0.0215 (4)
C17	0.47860 (19)	0.75520 (12)	0.19617 (12)	0.0224 (4)
H17	0.5599	0.7375	0.1683	0.027*
C18	0.33741 (18)	0.71173 (11)	0.16982 (11)	0.0203 (4)
C19	0.21512 (18)	0.74044 (11)	0.20790 (11)	0.0193 (3)
C20	0.2414 (2)	0.80721 (12)	0.27631 (12)	0.0249 (4)
H20	0.1605	0.8251	0.3044	0.030*
C21	0.3855 (2)	0.84870 (13)	0.30454 (12)	0.0262 (4)
H21	0.4026	0.8937	0.3526	0.031*
C22	0.4368 (2)	0.59651 (14)	0.08517 (15)	0.0368 (5)
H22A	0.4020	0.5462	0.0409	0.055*
H22B	0.5043	0.5716	0.1418	0.055*
H22C	0.4934	0.6420	0.0571	0.055*
C23	−0.05031 (19)	0.73108 (12)	0.20937 (13)	0.0260 (4)
H23A	−0.1430	0.6957	0.1814	0.039*
H23B	−0.0678	0.7965	0.1937	0.039*
H23C	−0.0268	0.7236	0.2771	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0180 (6)	0.0316 (7)	0.0312 (7)	0.0003 (5)	0.0050 (5)	−0.0126 (6)
O2	0.0152 (6)	0.0253 (6)	0.0258 (6)	−0.0021 (5)	0.0051 (5)	−0.0061 (5)
N1	0.0175 (8)	0.0197 (8)	0.0218 (8)	−0.0008 (7)	0.0042 (7)	−0.0027 (7)
C1'	0.0175 (8)	0.0197 (8)	0.0218 (8)	−0.0008 (7)	0.0042 (7)	−0.0027 (7)
N2	0.0214 (8)	0.0270 (8)	0.0354 (9)	−0.0022 (7)	0.0065 (7)	0.0011 (7)
N3	0.0209 (8)	0.0325 (9)	0.0240 (8)	−0.0045 (7)	−0.0028 (6)	0.0063 (7)
N4	0.0257 (8)	0.0309 (8)	0.0315 (8)	−0.0031 (7)	0.0065 (7)	0.0030 (7)
C1	0.0233 (8)	0.0196 (8)	0.0192 (8)	0.0004 (7)	0.0036 (7)	−0.0026 (7)
C2	0.0347 (10)	0.0209 (8)	0.0199 (8)	−0.0056 (8)	0.0056 (8)	−0.0035 (7)
C3	0.0391 (11)	0.0267 (10)	0.0308 (10)	−0.0063 (8)	0.0126 (9)	−0.0034 (8)
C4	0.0523 (13)	0.0317 (10)	0.0342 (11)	−0.0115 (10)	0.0219 (10)	−0.0042 (9)
C5	0.0717 (16)	0.0323 (11)	0.0272 (10)	−0.0162 (11)	0.0190 (11)	−0.0001 (9)
C6	0.0593 (14)	0.0284 (10)	0.0228 (9)	−0.0058 (10)	0.0013 (9)	0.0015 (8)
C7	0.0434 (11)	0.0237 (9)	0.0191 (9)	−0.0057 (8)	0.0026 (8)	−0.0020 (7)
C8	0.0400 (11)	0.0293 (10)	0.0217 (9)	0.0011 (9)	−0.0065 (8)	0.0023 (8)
C9	0.0298 (10)	0.0303 (10)	0.0225 (9)	−0.0031 (8)	−0.0041 (8)	0.0001 (8)
C10	0.0217 (8)	0.0244 (9)	0.0205 (8)	−0.0004 (7)	−0.0006 (7)	−0.0016 (7)
C11	0.0175 (8)	0.0229 (8)	0.0231 (8)	0.0010 (7)	0.0037 (7)	−0.0042 (7)
C12	0.0174 (8)	0.0204 (8)	0.0205 (8)	−0.0001 (7)	0.0051 (7)	−0.0015 (7)
C13	0.0180 (8)	0.0185 (8)	0.0216 (8)	0.0019 (7)	0.0031 (7)	−0.0025 (7)
C14	0.0246 (9)	0.0218 (9)	0.0218 (9)	0.0016 (8)	0.0068 (8)	0.0016 (7)
C15	0.0161 (8)	0.0247 (9)	0.0243 (9)	−0.0003 (7)	0.0007 (7)	−0.0036 (7)
C16	0.0159 (8)	0.0251 (8)	0.0210 (8)	0.0015 (7)	−0.0006 (7)	0.0023 (7)
C17	0.0164 (8)	0.0281 (9)	0.0225 (8)	0.0019 (7)	0.0041 (7)	−0.0008 (7)
C18	0.0198 (8)	0.0219 (8)	0.0184 (8)	0.0010 (7)	0.0026 (7)	−0.0027 (7)
C19	0.0151 (8)	0.0210 (8)	0.0203 (8)	−0.0001 (6)	0.0013 (7)	0.0029 (7)
C20	0.0195 (8)	0.0294 (9)	0.0266 (9)	−0.0019 (7)	0.0072 (7)	−0.0068 (7)
C21	0.0230 (9)	0.0300 (10)	0.0247 (9)	−0.0023 (8)	0.0035 (7)	−0.0072 (8)
C22	0.0242 (10)	0.0402 (12)	0.0475 (12)	0.0015 (9)	0.0115 (9)	−0.0201 (10)
C23	0.0168 (8)	0.0287 (9)	0.0334 (10)	−0.0011 (7)	0.0079 (7)	−0.0061 (8)

Geometric parameters (Å, º) top

O1—C18	1.370 (2)	C8—H8A	0.9900
O1—C22	1.436 (2)	C8—H8B	0.9900
O2—C19	1.3690 (19)	C9—C10	1.512 (2)
O2—C23	1.434 (2)	C9—H9A	0.9900
N1—C1	1.397 (2)	C9—H9B	0.9900
N1—C13	1.411 (2)	C10—C11	1.391 (2)
N2—C14	1.153 (2)	C11—C12	1.400 (2)
N3—C13	1.351 (2)	C11—C16	1.494 (2)
N3—H1	0.95 (2)	C12—C13	1.413 (2)
N3—H2	0.92 (2)	C12—C15	1.436 (2)
N4—C15	1.150 (2)	C16—C21	1.374 (2)
C1—C10	1.413 (2)	C16—C17	1.399 (2)
C1—C2	1.484 (2)	C17—C18	1.383 (2)
C2—C3	1.396 (3)	C17—H17	0.9500
C2—C7	1.405 (3)	C18—C19	1.403 (2)
C3—C4	1.386 (3)	C19—C20	1.380 (2)
C3—H3	0.9500	C20—C21	1.394 (2)
C4—C5	1.381 (3)	C20—H20	0.9500
C4—H4	0.9500	C21—H21	0.9500
C5—C6	1.386 (3)	C22—H22A	0.9800
C5—H5	0.9500	C22—H22B	0.9800
C6—C7	1.392 (3)	C22—H22C	0.9800
C6—H6	0.9500	C23—H23A	0.9800
C7—C8	1.499 (3)	C23—H23B	0.9800
C8—C9	1.528 (3)	C23—H23C	0.9800

C18—O1—C22	115.94 (13)	C1—C10—C9	117.78 (15)
C19—O2—C23	116.23 (13)	C10—C11—C12	120.31 (15)
C1—N1—C13	121.85 (15)	C10—C11—C16	120.23 (15)
C13—N3—H1	121.0 (15)	C12—C11—C16	119.45 (15)
C13—N3—H2	121.2 (13)	C11—C12—C13	121.05 (15)
H1—N3—H2	117.7 (19)	C11—C12—C15	120.84 (14)
N1—C1—C10	119.15 (15)	C13—C12—C15	118.10 (14)
N1—C1—C2	122.66 (15)	N3—C13—N1	121.00 (15)
C10—C1—C2	118.16 (15)	N3—C13—C12	121.45 (16)
C3—C2—C7	119.44 (17)	N1—C13—C12	117.52 (14)
C3—C2—C1	122.73 (17)	N4—C15—C12	177.44 (18)
C7—C2—C1	117.76 (16)	C21—C16—C17	119.08 (15)
C4—C3—C2	120.60 (19)	C21—C16—C11	121.48 (15)
C4—C3—H3	119.7	C17—C16—C11	119.44 (15)
C2—C3—H3	119.7	C18—C17—C16	120.75 (15)
C5—C4—C3	119.7 (2)	C18—C17—H17	119.6
C5—C4—H4	120.1	C16—C17—H17	119.6
C3—C4—H4	120.1	O1—C18—C17	124.52 (15)
C4—C5—C6	120.47 (19)	O1—C18—C19	115.72 (14)
C4—C5—H5	119.8	C17—C18—C19	119.76 (15)
C6—C5—H5	119.8	O2—C19—C20	124.56 (15)
C5—C6—C7	120.5 (2)	O2—C19—C18	116.35 (14)
C5—C6—H6	119.7	C20—C19—C18	119.08 (15)
C7—C6—H6	119.7	C19—C20—C21	120.66 (16)
C6—C7—C2	119.19 (19)	C19—C20—H20	119.7
C6—C7—C8	122.56 (18)	C21—C20—H20	119.7
C2—C7—C8	118.19 (16)	C16—C21—C20	120.48 (16)
C7—C8—C9	108.73 (16)	C16—C21—H21	119.8
C7—C8—H8A	109.9	C20—C21—H21	119.8
C9—C8—H8A	109.9	O1—C22—H22A	109.5
C7—C8—H8B	109.9	O1—C22—H22B	109.5
C9—C8—H8B	109.9	H22A—C22—H22B	109.5
H8A—C8—H8B	108.3	O1—C22—H22C	109.5
C10—C9—C8	109.33 (14)	H22A—C22—H22C	109.5
C10—C9—H9A	109.8	H22B—C22—H22C	109.5
C8—C9—H9A	109.8	O2—C23—H23A	109.5
C10—C9—H9B	109.8	O2—C23—H23B	109.5
C8—C9—H9B	109.8	H23A—C23—H23B	109.5
H9A—C9—H9B	108.3	O2—C23—H23C	109.5
C11—C10—C1	119.86 (15)	H23A—C23—H23C	109.5
C11—C10—C9	122.36 (15)	H23B—C23—H23C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O1ⁱ	0.95 (2)	2.24 (2)	2.927 (2)	129 (2)
N3—H2···O2ⁱ	0.92 (2)	2.25 (2)	2.987 (2)	136 (2)

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

Experimental details

Crystal data
Chemical formula	0.05C₂₂H₁₉N₃O₂·0.95C₂₄H₁₉N₃O₂
M_r	380.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.9347 (3), 14.4915 (5), 14.7818 (6)
β (°)	103.446 (4)
V (Å³)	1861.45 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.974, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	9240, 4160, 3146
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.124, 1.04
No. of reflections	4160
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)	0.30, −0.24

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
N3—H1···O1ⁱ	0.95 (2)	2.24 (2)	2.927 (2)	129 (2)
N3—H2···O2ⁱ	0.92 (2)	2.25 (2)	2.987 (2)	136 (2)

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

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
Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M. & Ng, S. W. (2011). Acta Cryst. E67, o2872. Web of Science CSD CrossRef IUCr Journals Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals 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 11| November 2011| Page o2873

doi:10.1107/S1600536811040517

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

2-Amino-4-(3,4-dimeth­­oxy­phen­yl)-5,6-di­hydro­benzo[h]quinoline-3-carbo­nitrile–3-amino-1-(3,4-dimeth­­oxy­phen­yl)-9,10-di­hydro­phenanthrene-2,4-dicarbo­nitrile (1/19)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Amino-4-(3,4-dimethoxyphenyl)-5,6-dihydrobenzo[h]quinoline-3-carbonitrile–3-amino-1-(3,4-dimethoxyphenyl)-9,10-dihydrophenanthrene-2,4-dicarbonitrile (1/19)