3-Amino-1-phenyl-1H-benzo[f]chromene-2-carbonitrile

Akkurt, M.; Kennedy, A.R.; Mohamed, S.K.; Younes, S.H.H.; Miller, G.J.

doi:10.1107/S1600536813004376

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Page o401

doi:10.1107/S1600536813004376

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3-Amino-1-phenyl-1H-benzo[f]chromene-2-carbonitrile

Mehmet Akkurt,^a ^* Alan R. Kennedy,^b Shaaban Kamel Mohamed,^c,^d ^* Sabry H. H. Younes ^e and Gary J. Miller ^f

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, ^cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and ^fAnalytical Sciences, Manchester Metropolitan University, Manchester M1 5GD, England
^*Correspondence e-mail: akkurt@erciyes.edu.tr, shaabankamel@yahoo.com

(Received 13 February 2013; accepted 14 February 2013; online 20 February 2013)

In the title compound, C₂₀H₁₄N₂O, the phenyl ring is almost normal to the naphthalene ring system with a dihedral angle of 86.72 (9)°. The 4H-pyran ring fused with the naphthalene ring system has a boat conformation. In the crystal, molecules are linked into a helical supramolecular chain along the b axis via N—H⋯N hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C—H⋯π interactions.

Related literature

For biological and industrial applications of chromene compounds, see, for example: Ellis & Lockhart (2007 ); Horton et al. (2003 ). For puckering parameters, see: Cremer & Pople (1975 ). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₁₄N₂O
M_r = 298.33
Monoclinic, P 2₁
a = 9.4059 (8) Å
b = 6.5009 (5) Å
c = 12.4919 (10) Å
β = 105.914 (9)°
V = 734.57 (11) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 123 K
0.30 × 0.12 × 0.07 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.955, T_max = 1.000
3674 measured reflections
2780 independent reflections
2477 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.091
S = 1.06
2780 reflections
217 parameters
49 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C4/C5/C10–C13 and C5–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2ⁱ	0.90 (3)	2.16 (2)	2.978 (3)	150 (2)
N1—H2N⋯N2ⁱⁱ	0.87 (3)	2.33 (3)	3.138 (3)	154 (2)
C7—H7⋯Cg3ⁱⁱⁱ	0.95	2.84	3.561 (2)	133
C12—H12⋯Cg2^iv	0.95	2.68	3.446 (2)	139
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z]$ ; (ii) x, y-1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iv) $[-x+2, y-{\script{1\over 2}}, -z+1]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813004376/tk5198sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004376/tk5198Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004376/tk5198Isup3.cml

checkCIF report

Comment top

Chromenes are components of many natural products (Ellis & Lockhart, 2007) and incorporated in numerous medicinal drugs as significant chromophores. They have shown to display anti-viral, anti-tumoral, anti-anaphylactic, spasmolytic, diuretic and clotting activity (Horton et al., 2003). Furthermore, they can be used as photo-active materials, biodegradable agrochemicals and pigments. As a part of our structural investigations on functionalized chromenes and compounds containing the benzopyran fragment, the single-crystal X-ray diffraction study on the title compound was carried out.

In the title compound (I), Fig. 1, the C14–C19 phenyl ring and the C4–C13 naphthalene ring system is essentially planar with the maximum deviations of -0.004 (2) Å for C16 and 0.015 (2) Å for C4, respectively. They make a dihedral angle of 86.72 (9)° with each other.

The 4H-pyran ring (O1/C1–C4/C13) in (I) is puckered with the puckering parameters (Cremer & Pople, 1975) of Q_T = 0.211 (2) Å, θ = 96.2 (5)° and ϕ = 348.9 (6)°. The N1–C1–O1–C13 and N1–C1–C2–C20 torsion angles are -165.54 (17) and -2.6 (3)°, respectively.

In the crystal structure, molecules are linked into a helical supramolecular chain along the b axis via N—H···N hydrogen bonds (Table 1). Three distinct molecules are linked by three such connections involving two acceptors to generate a R³₂(10) ring motif (Fig. 2; Bernstein et al., 1995). Chains are consolidated into a three-dimensional architecture by C—H···π interactions.

Related literature top

For biological and industrial applications of chromene compounds, see, for example: Ellis & Lockhart (2007); Horton et al. (2003). For puckering parameters, see: Cremer & Pople (1975). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

Benzylidenepropanedinitrile (1.54 g; 10 mmol) was dissolved in ethanol (50 ml), followed by addition of naphthalen-2-ol (1.44 g; 10 mmol) and a catalytic amount of TEA. The mixture was stirred and refluxed for 2 h at 350 K. The solid product was deposited on cooling at room temperature and collected by filtration. The crude product was washed by cold ethanol, dried under vacuum and recrystallized from ethanol to give high quality crystals (M.pt: 563 K) suitable for X-ray analysis in an excellent yield (91%).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing the labelling of the non-H atoms and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. View of the N—H···N hydrogen bonds, having R³₂(10) ring motifs, forming chains along the b axis. H atoms not involved in hydrogen bonds have been omitted for clarity.

3-Amino-1-phenyl-1H-benzo[f]chromene-2-carbonitrile top

Crystal data top

C₂₀H₁₄N₂O	F(000) = 312
M_r = 298.33	D_x = 1.349 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1797 reflections
a = 9.4059 (8) Å	θ = 3.1–28.7°
b = 6.5009 (5) Å	µ = 0.09 mm⁻¹
c = 12.4919 (10) Å	T = 123 K
β = 105.914 (9)°	Rod, colourless
V = 734.57 (11) Å³	0.30 × 0.12 × 0.07 mm
Z = 2

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2780 independent reflections
Radiation source: fine-focus sealed tube	2477 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Detector resolution: 16.0727 pixels mm^-1	θ_max = 28.8°, θ_min = 3.2°
ω scans	h = −12→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→8
T_min = 0.955, T_max = 1.000	l = −16→16
3674 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0342P)² + 0.0595P] where P = (F_o² + 2F_c²)/3
2780 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.22 e Å⁻³
49 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₀H₁₄N₂O	V = 734.57 (11) Å³
M_r = 298.33	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.4059 (8) Å	µ = 0.09 mm⁻¹
b = 6.5009 (5) Å	T = 123 K
c = 12.4919 (10) Å	0.30 × 0.12 × 0.07 mm
β = 105.914 (9)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	2780 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2477 reflections with I > 2σ(I)
T_min = 0.955, T_max = 1.000	R_int = 0.019
3674 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	49 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.22 e Å⁻³
2780 reflections	Δρ_min = −0.18 e Å⁻³
217 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.91532 (15)	0.1653 (2)	0.28251 (11)	0.0225 (4)
N1	1.0215 (2)	0.2373 (3)	0.14856 (16)	0.0243 (6)
N2	0.9541 (2)	0.7742 (3)	0.08334 (15)	0.0294 (6)
C1	0.9372 (2)	0.3114 (3)	0.21116 (15)	0.0192 (6)
C2	0.8832 (2)	0.5038 (3)	0.21023 (16)	0.0188 (6)
C3	0.7813 (2)	0.5686 (3)	0.28021 (16)	0.0173 (6)
C4	0.7940 (2)	0.4143 (3)	0.37246 (15)	0.0166 (6)
C5	0.7408 (2)	0.4592 (3)	0.46701 (16)	0.0178 (6)
C6	0.6672 (2)	0.6459 (4)	0.47667 (16)	0.0207 (6)
C7	0.6185 (2)	0.6844 (4)	0.56872 (17)	0.0252 (7)
C8	0.6400 (2)	0.5410 (3)	0.65490 (17)	0.0273 (7)
C9	0.7100 (2)	0.3578 (4)	0.64841 (17)	0.0246 (7)
C10	0.7613 (2)	0.3129 (3)	0.55449 (16)	0.0197 (6)
C11	0.8330 (2)	0.1247 (3)	0.54667 (16)	0.0213 (6)
C12	0.8812 (2)	0.0815 (3)	0.45537 (16)	0.0197 (6)
C13	0.8601 (2)	0.2280 (3)	0.37026 (16)	0.0183 (6)
C14	0.6240 (2)	0.6022 (3)	0.20788 (15)	0.0201 (6)
C15	0.5843 (2)	0.7921 (4)	0.15674 (16)	0.0275 (7)
C16	0.4429 (3)	0.8218 (4)	0.08696 (18)	0.0357 (8)
C17	0.3403 (3)	0.6645 (5)	0.06874 (18)	0.0398 (9)
C18	0.3793 (3)	0.4760 (5)	0.11953 (19)	0.0368 (8)
C19	0.5205 (2)	0.4453 (4)	0.18836 (17)	0.0271 (7)
C20	0.9215 (2)	0.6514 (4)	0.13967 (16)	0.0209 (6)
H1N	1.024 (3)	0.297 (4)	0.084 (2)	0.038 (7)*
H2N	1.032 (3)	0.104 (5)	0.146 (2)	0.043 (8)*
H3	0.81820	0.70340	0.31560	0.0210*
H6	0.65140	0.74520	0.41880	0.0250*
H7	0.56950	0.81030	0.57390	0.0300*
H8	0.60620	0.57030	0.71830	0.0330*
H9	0.72390	0.26070	0.70720	0.0290*
H11	0.84780	0.02730	0.60540	0.0260*
H12	0.92820	−0.04580	0.44970	0.0240*
H15	0.65400	0.90140	0.16960	0.0330*
H16	0.41660	0.95100	0.05160	0.0430*
H17	0.24350	0.68570	0.02150	0.0480*
H18	0.30910	0.36740	0.10720	0.0440*
H19	0.54670	0.31510	0.22260	0.0330*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0282 (8)	0.0207 (8)	0.0215 (7)	0.0020 (7)	0.0116 (6)	0.0011 (7)
N1	0.0270 (10)	0.0260 (12)	0.0227 (9)	0.0022 (8)	0.0118 (8)	0.0002 (9)
N2	0.0353 (11)	0.0279 (11)	0.0302 (10)	0.0016 (9)	0.0179 (9)	0.0030 (9)
C1	0.0177 (10)	0.0237 (12)	0.0151 (9)	−0.0048 (9)	0.0028 (8)	−0.0008 (9)
C2	0.0183 (10)	0.0216 (11)	0.0169 (9)	−0.0027 (8)	0.0054 (8)	0.0008 (9)
C3	0.0177 (10)	0.0169 (11)	0.0179 (9)	−0.0023 (8)	0.0059 (7)	−0.0017 (9)
C4	0.0142 (10)	0.0180 (11)	0.0161 (9)	−0.0032 (8)	0.0019 (7)	0.0004 (9)
C5	0.0126 (9)	0.0225 (11)	0.0178 (9)	−0.0037 (8)	0.0034 (8)	0.0000 (9)
C6	0.0187 (10)	0.0226 (11)	0.0209 (9)	−0.0015 (9)	0.0057 (8)	0.0018 (10)
C7	0.0224 (11)	0.0260 (13)	0.0292 (11)	0.0004 (9)	0.0105 (9)	−0.0024 (10)
C8	0.0269 (12)	0.0371 (15)	0.0207 (10)	−0.0030 (10)	0.0114 (9)	−0.0025 (10)
C9	0.0242 (11)	0.0305 (13)	0.0192 (10)	−0.0030 (10)	0.0063 (8)	0.0029 (10)
C10	0.0169 (10)	0.0248 (12)	0.0164 (9)	−0.0023 (9)	0.0030 (8)	0.0003 (9)
C11	0.0218 (11)	0.0224 (12)	0.0178 (10)	−0.0025 (9)	0.0020 (8)	0.0026 (10)
C12	0.0174 (10)	0.0180 (11)	0.0217 (10)	−0.0002 (9)	0.0019 (8)	0.0013 (10)
C13	0.0185 (10)	0.0211 (12)	0.0152 (9)	−0.0033 (8)	0.0047 (8)	−0.0034 (9)
C14	0.0212 (10)	0.0269 (12)	0.0131 (9)	0.0041 (9)	0.0061 (8)	0.0011 (9)
C15	0.0292 (12)	0.0301 (13)	0.0238 (10)	0.0070 (10)	0.0085 (9)	0.0055 (11)
C16	0.0358 (13)	0.0479 (16)	0.0227 (11)	0.0204 (12)	0.0069 (10)	0.0096 (12)
C17	0.0227 (12)	0.073 (2)	0.0219 (11)	0.0134 (13)	0.0033 (9)	0.0024 (14)
C18	0.0208 (11)	0.0592 (17)	0.0291 (12)	−0.0029 (12)	0.0046 (9)	−0.0022 (13)
C19	0.0231 (11)	0.0346 (14)	0.0226 (10)	−0.0019 (10)	0.0044 (9)	−0.0003 (11)
C20	0.0223 (10)	0.0235 (11)	0.0181 (9)	0.0019 (9)	0.0077 (8)	−0.0035 (10)

Geometric parameters (Å, º) top

O1—C1	1.356 (2)	C11—C12	1.367 (3)
O1—C13	1.396 (2)	C12—C13	1.400 (3)
N1—C1	1.346 (3)	C14—C19	1.385 (3)
N2—C20	1.160 (3)	C14—C15	1.393 (3)
N1—H1N	0.90 (3)	C15—C16	1.389 (3)
N1—H2N	0.87 (3)	C16—C17	1.381 (4)
C1—C2	1.349 (3)	C17—C18	1.382 (4)
C2—C20	1.415 (3)	C18—C19	1.385 (3)
C2—C3	1.523 (3)	C3—H3	1.0000
C3—C4	1.508 (3)	C6—H6	0.9500
C3—C14	1.523 (3)	C7—H7	0.9500
C4—C13	1.365 (3)	C8—H8	0.9500
C4—C5	1.433 (3)	C9—H9	0.9500
C5—C10	1.421 (3)	C11—H11	0.9500
C5—C6	1.419 (3)	C12—H12	0.9500
C6—C7	1.372 (3)	C15—H15	0.9500
C7—C8	1.396 (3)	C16—H16	0.9500
C8—C9	1.374 (3)	C17—H17	0.9500
C9—C10	1.416 (3)	C18—H18	0.9500
C10—C11	1.413 (3)	C19—H19	0.9500

C1—O1—C13	117.88 (15)	C15—C14—C19	119.01 (18)
H1N—N1—H2N	111 (2)	C14—C15—C16	120.1 (2)
C1—N1—H1N	122.0 (17)	C15—C16—C17	120.4 (2)
C1—N1—H2N	117.8 (18)	C16—C17—C18	119.7 (2)
O1—C1—C2	122.03 (17)	C17—C18—C19	120.1 (3)
O1—C1—N1	110.54 (17)	C14—C19—C18	120.8 (2)
N1—C1—C2	127.39 (19)	N2—C20—C2	178.9 (2)
C1—C2—C3	123.11 (17)	C2—C3—H3	107.00
C1—C2—C20	118.34 (19)	C4—C3—H3	107.00
C3—C2—C20	118.54 (18)	C14—C3—H3	107.00
C2—C3—C14	111.16 (16)	C5—C6—H6	120.00
C4—C3—C14	114.16 (16)	C7—C6—H6	120.00
C2—C3—C4	108.92 (16)	C6—C7—H7	120.00
C3—C4—C13	121.06 (17)	C8—C7—H7	120.00
C3—C4—C5	121.46 (17)	C7—C8—H8	120.00
C5—C4—C13	117.46 (17)	C9—C8—H8	120.00
C4—C5—C6	122.21 (18)	C8—C9—H9	120.00
C4—C5—C10	119.53 (17)	C10—C9—H9	120.00
C6—C5—C10	118.26 (18)	C10—C11—H11	120.00
C5—C6—C7	120.7 (2)	C12—C11—H11	120.00
C6—C7—C8	120.9 (2)	C11—C12—H12	121.00
C7—C8—C9	120.24 (19)	C13—C12—H12	121.00
C8—C9—C10	120.4 (2)	C14—C15—H15	120.00
C5—C10—C9	119.60 (19)	C16—C15—H15	120.00
C5—C10—C11	119.53 (17)	C15—C16—H16	120.00
C9—C10—C11	120.88 (19)	C17—C16—H16	120.00
C10—C11—C12	120.61 (18)	C16—C17—H17	120.00
C11—C12—C13	118.90 (18)	C18—C17—H17	120.00
O1—C13—C12	113.06 (16)	C17—C18—H18	120.00
O1—C13—C4	122.98 (17)	C19—C18—H18	120.00
C4—C13—C12	123.96 (18)	C14—C19—H19	120.00
C3—C14—C15	119.59 (17)	C18—C19—H19	120.00
C3—C14—C19	121.37 (18)

C13—O1—C1—N1	165.54 (17)	C5—C4—C13—O1	179.45 (17)
C13—O1—C1—C2	−12.3 (3)	C5—C4—C13—C12	−1.3 (3)
C1—O1—C13—C4	16.6 (3)	C4—C5—C6—C7	−179.59 (19)
C1—O1—C13—C12	−162.72 (17)	C10—C5—C6—C7	0.6 (3)
O1—C1—C2—C3	−6.1 (3)	C4—C5—C10—C9	179.43 (18)
O1—C1—C2—C20	174.79 (17)	C4—C5—C10—C11	−0.4 (3)
N1—C1—C2—C3	176.45 (19)	C6—C5—C10—C9	−0.8 (3)
N1—C1—C2—C20	−2.6 (3)	C6—C5—C10—C11	179.40 (18)
C1—C2—C3—C4	18.5 (3)	C5—C6—C7—C8	−0.1 (3)
C1—C2—C3—C14	−108.1 (2)	C6—C7—C8—C9	−0.3 (3)
C20—C2—C3—C4	−162.42 (17)	C7—C8—C9—C10	0.2 (3)
C20—C2—C3—C14	71.0 (2)	C8—C9—C10—C5	0.4 (3)
C2—C3—C4—C5	164.30 (17)	C8—C9—C10—C11	−179.78 (19)
C2—C3—C4—C13	−14.1 (3)	C5—C10—C11—C12	−0.7 (3)
C14—C3—C4—C5	−70.8 (2)	C9—C10—C11—C12	179.46 (19)
C14—C3—C4—C13	110.8 (2)	C10—C11—C12—C13	0.8 (3)
C2—C3—C14—C15	−85.4 (2)	C11—C12—C13—O1	179.53 (17)
C2—C3—C14—C19	92.2 (2)	C11—C12—C13—C4	0.2 (3)
C4—C3—C14—C15	150.88 (18)	C3—C14—C15—C16	177.37 (19)
C4—C3—C14—C19	−31.5 (3)	C19—C14—C15—C16	−0.3 (3)
C3—C4—C5—C6	3.1 (3)	C3—C14—C19—C18	−177.9 (2)
C3—C4—C5—C10	−177.07 (18)	C15—C14—C19—C18	−0.3 (3)
C13—C4—C5—C6	−178.44 (19)	C14—C15—C16—C17	0.7 (3)
C13—C4—C5—C10	1.4 (3)	C15—C16—C17—C18	−0.6 (4)
C3—C4—C13—O1	−2.1 (3)	C16—C17—C18—C19	0.1 (4)
C3—C4—C13—C12	177.14 (18)	C17—C18—C19—C14	0.4 (4)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C4/C5/C10–C13 and C5–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2ⁱ	0.90 (3)	2.16 (2)	2.978 (3)	150 (2)
N1—H2N···N2ⁱⁱ	0.87 (3)	2.33 (3)	3.138 (3)	154 (2)
C7—H7···Cg3ⁱⁱⁱ	0.95	2.84	3.561 (2)	133
C12—H12···Cg2^iv	0.95	2.68	3.446 (2)	139

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄N₂O
M_r	298.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	123
a, b, c (Å)	9.4059 (8), 6.5009 (5), 12.4919 (10)
β (°)	105.914 (9)
V (Å³)	734.57 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.12 × 0.07

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.955, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3674, 2780, 2477
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.678

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.091, 1.06
No. of reflections	2780
No. of parameters	217
No. of restraints	49
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C4/C5/C10–C13 and C5–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2ⁱ	0.90 (3)	2.16 (2)	2.978 (3)	150 (2)
N1—H2N···N2ⁱⁱ	0.87 (3)	2.33 (3)	3.138 (3)	154 (2)
C7—H7···Cg3ⁱⁱⁱ	0.95	2.84	3.561 (2)	133
C12—H12···Cg2^iv	0.95	2.68	3.446 (2)	139

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

Acknowledgements

Manchester Metropolitan University, Erciyes University and University of Strathclyde are gratefully acknowledged for supporting this study.

References

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