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

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, mol-ecules are linked into a helical supra-molecular chain along the b axis via N-H⋯N hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C-H⋯π inter-actions.

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 = 298.33

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.091

S = 1.06

2780 reflections

217 parameters

49 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004376/tk5198sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004376/tk5198Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H14N2O	F(000) = 312
Mr = 298.33	Dx = 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

Oxford Diffraction Xcalibur Eos diffractometer	2780 independent reflections
Radiation source: fine-focus sealed tube	2477 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 16.0727 pixels mm-1	θmax = 28.8°, θmin = 3.2°
ω scans	h = −12→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −7→8
Tmin = 0.955, Tmax = 1.000	l = −16→16
3674 measured reflections

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(Fo2) + (0.0342P)2 + 0.0595P] where P = (Fo2 + 2Fc2)/3
2780 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.22 e Å−3
49 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cg2iv	0.95	2.68	3.446 (2)	139

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⋯Cg2iv	0.95	2.68	3.446 (2)	139

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .