Crystal structure of 3-amino-1-(4-hy-droxy-phen-yl)-1H-benzo[f]chromene-2-carbo-nitrile.

In the title compound, C20H14N2O2, the hy-droxy-benzene ring is almost perpendicular to the mean plane of the naphthalene ring system, making a dihedral angle of 85.56 (4)°. The 4H-pyran ring fused with the naphthalene ring system has a flattened boat conformation. In the crystal, O-H⋯N and N-H⋯O hydrogen bonds link the mol-ecules into a supra-molecular layer in the bc plane; N-H⋯π inter-actions also contribute to this arrangement. The layers are linked by weak by C-H⋯π and π-π [inter-centroid separation = 3.8713 (7) Å] inter-actions.

Related literature

For the biological activity of some heterocyclic derivatives containing the 4H-pyran unit, see: Elnagdi et al. (1983 ▸); Goldmann & Stoltefus (1991 ▸); Perez-Perez et al. (1995 ▸); Fan et al. (2010 ▸); Aytemir et al. (2004 ▸); Uher et al. (1994 ▸). For similar structures, see: Akkurt et al. (2013 ▸, 2015 ▸).

Experimental

Crystal data

C20H14N2O2

M = 314.33

Monoclinic,

a = 12.1086 (8) Å

b = 13.1418 (9) Å

c = 10.1552 (7) Å

β = 96.992 (1)°

V = 1603.97 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.21 × 0.08 × 0.07 mm

Data collection

Rigaku AFC12 (Right) diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012 ▸) T min = 0.738, T max = 1.000

17411 measured reflections

3679 independent reflections

3251 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.06

3679 reflections

229 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2012 ▸); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015012566/tk5372sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015012566/tk5372Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015012566/tk5372Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015012566/tk5372fig1.tif

View of the title compound with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015012566/tk5372fig2.tif

View of the packing of the title compound viewing down a axis.

CCDC reference: 1409621

Additional supporting information: crystallographic information; 3D view; checkCIF report

C20H14N2O2	F(000) = 656
Mr = 314.33	Dx = 1.302 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71075 Å
a = 12.1086 (8) Å	Cell parameters from 17749 reflections
b = 13.1418 (9) Å	θ = 2.3–27.5°
c = 10.1552 (7) Å	µ = 0.09 mm−1
β = 96.992 (1)°	T = 100 K
V = 1603.97 (19) Å3	Blade, colourless
Z = 4	0.21 × 0.08 × 0.07 mm

Rigaku AFC12 (Right) diffractometer	3679 independent reflections
Radiation source: Rotating Anode	3251 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm-1	Rint = 0.030
profile data from ω–scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	h = −15→15
Tmin = 0.738, Tmax = 1.000	k = −17→14
17411 measured reflections	l = −12→13

Refinement on F2	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.092	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.4007P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
3679 reflections	Δρmax = 0.26 e Å−3
229 parameters	Δρmin = −0.18 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
C1	0.33983 (8)	0.47639 (8)	1.11802 (10)	0.0237 (2)
C2	0.31777 (8)	0.53512 (7)	1.00751 (9)	0.0225 (2)
C3	0.22804 (8)	0.50920 (7)	0.89492 (9)	0.02158 (19)
H3	0.1865	0.5730	0.8672	0.026*
C4	0.14741 (8)	0.43453 (7)	0.94430 (10)	0.0234 (2)
C5	0.04093 (8)	0.41495 (8)	0.87013 (10)	0.0261 (2)
C6	0.00288 (9)	0.46750 (8)	0.75126 (11)	0.0295 (2)
H6	0.0494	0.5170	0.7178	0.035*
C7	−0.10048 (9)	0.44795 (9)	0.68361 (12)	0.0356 (3)
H7	−0.1250	0.4847	0.6049	0.043*
C8	−0.17001 (9)	0.37399 (10)	0.73009 (13)	0.0380 (3)
H8	−0.2408	0.3603	0.6822	0.046*
C9	−0.13586 (9)	0.32188 (9)	0.84389 (13)	0.0363 (3)
H9	−0.1836	0.2722	0.8747	0.044*
C10	−0.03025 (9)	0.34047 (8)	0.91728 (11)	0.0300 (2)
C11	0.00527 (9)	0.28765 (9)	1.03649 (12)	0.0348 (3)
H11	−0.0417	0.2374	1.0675	0.042*
C12	0.10573 (9)	0.30770 (8)	1.10727 (12)	0.0325 (2)
H12	0.1287	0.2723	1.1875	0.039*
C13	0.17513 (8)	0.38188 (8)	1.05958 (10)	0.0256 (2)
C14	0.38247 (9)	0.62331 (8)	0.99791 (10)	0.0264 (2)
C15	0.27956 (8)	0.46801 (7)	0.77552 (9)	0.02106 (19)
C16	0.32470 (8)	0.37029 (7)	0.77790 (10)	0.0233 (2)
H16	0.3201	0.3280	0.8529	0.028*
C17	0.37626 (8)	0.33360 (7)	0.67264 (10)	0.0237 (2)
H17	0.4067	0.2669	0.6758	0.028*
C18	0.38308 (8)	0.39533 (8)	0.56223 (9)	0.0235 (2)
C19	0.33979 (9)	0.49308 (8)	0.55907 (10)	0.0272 (2)
H19	0.3453	0.5357	0.4846	0.033*
C20	0.28830 (8)	0.52852 (8)	0.66516 (10)	0.0255 (2)
H20	0.2585	0.5955	0.6622	0.031*
N1	0.42225 (8)	0.48875 (8)	1.21728 (9)	0.0297 (2)
N2	0.43322 (9)	0.69661 (8)	0.99112 (10)	0.0383 (2)
O1	0.27537 (6)	0.39555 (6)	1.14083 (7)	0.02776 (17)
O2	0.43199 (7)	0.36270 (6)	0.45510 (7)	0.02998 (18)
H1N	0.4259 (12)	0.4453 (10)	1.2856 (13)	0.042 (4)*
H2N	0.4767 (11)	0.5317 (10)	1.2069 (14)	0.041 (4)*
H2O	0.4737 (13)	0.3086 (11)	0.4770 (16)	0.057 (5)*

	U11	U22	U33	U12	U13	U23
C1	0.0230 (5)	0.0260 (5)	0.0232 (5)	0.0009 (4)	0.0073 (4)	−0.0010 (4)
C2	0.0224 (5)	0.0251 (5)	0.0207 (4)	−0.0014 (4)	0.0050 (3)	−0.0007 (4)
C3	0.0210 (4)	0.0223 (4)	0.0217 (4)	0.0009 (3)	0.0037 (3)	0.0003 (3)
C4	0.0221 (5)	0.0226 (5)	0.0266 (5)	0.0006 (4)	0.0074 (4)	−0.0028 (4)
C5	0.0226 (5)	0.0257 (5)	0.0312 (5)	0.0012 (4)	0.0080 (4)	−0.0073 (4)
C6	0.0246 (5)	0.0322 (5)	0.0318 (5)	0.0016 (4)	0.0040 (4)	−0.0067 (4)
C7	0.0281 (5)	0.0410 (6)	0.0370 (6)	0.0051 (5)	0.0009 (4)	−0.0108 (5)
C8	0.0223 (5)	0.0430 (7)	0.0483 (7)	0.0012 (5)	0.0022 (5)	−0.0184 (5)
C9	0.0251 (5)	0.0330 (6)	0.0529 (7)	−0.0045 (4)	0.0130 (5)	−0.0159 (5)
C10	0.0249 (5)	0.0266 (5)	0.0405 (6)	−0.0014 (4)	0.0116 (4)	−0.0089 (4)
C11	0.0317 (5)	0.0279 (5)	0.0477 (7)	−0.0057 (4)	0.0164 (5)	−0.0007 (5)
C12	0.0338 (6)	0.0287 (5)	0.0370 (6)	−0.0008 (4)	0.0119 (5)	0.0051 (4)
C13	0.0237 (5)	0.0250 (5)	0.0293 (5)	0.0004 (4)	0.0075 (4)	−0.0004 (4)
C14	0.0277 (5)	0.0328 (5)	0.0189 (4)	−0.0026 (4)	0.0035 (4)	0.0001 (4)
C15	0.0190 (4)	0.0237 (5)	0.0204 (4)	−0.0002 (3)	0.0020 (3)	−0.0005 (3)
C16	0.0251 (5)	0.0232 (5)	0.0221 (4)	−0.0006 (4)	0.0046 (4)	0.0033 (4)
C17	0.0251 (5)	0.0206 (4)	0.0258 (5)	0.0017 (4)	0.0045 (4)	0.0009 (4)
C18	0.0224 (4)	0.0285 (5)	0.0196 (4)	0.0012 (4)	0.0032 (3)	−0.0011 (4)
C19	0.0308 (5)	0.0294 (5)	0.0215 (5)	0.0051 (4)	0.0045 (4)	0.0067 (4)
C20	0.0279 (5)	0.0238 (5)	0.0249 (5)	0.0058 (4)	0.0039 (4)	0.0033 (4)
N1	0.0284 (5)	0.0386 (5)	0.0218 (4)	−0.0026 (4)	0.0020 (3)	0.0042 (4)
N2	0.0448 (6)	0.0404 (6)	0.0292 (5)	−0.0161 (5)	0.0028 (4)	0.0030 (4)
O1	0.0269 (4)	0.0280 (4)	0.0285 (4)	−0.0009 (3)	0.0036 (3)	0.0063 (3)
O2	0.0364 (4)	0.0326 (4)	0.0223 (4)	0.0095 (3)	0.0091 (3)	0.0022 (3)

C1—N1	1.3393 (13)	C11—C12	1.3612 (17)
C1—O1	1.3548 (12)	C11—H11	0.9500
C1—C2	1.3614 (14)	C12—C13	1.4108 (14)
C2—C14	1.4089 (14)	C12—H12	0.9500
C2—C3	1.5171 (13)	C13—O1	1.3937 (12)
C3—C4	1.5122 (13)	C14—N2	1.1492 (14)
C3—C15	1.5286 (13)	C15—C20	1.3887 (13)
C3—H3	1.0000	C15—C16	1.3948 (13)
C4—C13	1.3661 (14)	C16—C17	1.3883 (13)
C4—C5	1.4351 (14)	C16—H16	0.9500
C5—C6	1.4180 (15)	C17—C18	1.3945 (13)
C5—C10	1.4250 (15)	C17—H17	0.9500
C6—C7	1.3765 (15)	C18—O2	1.3693 (11)
C6—H6	0.9500	C18—C19	1.3864 (14)
C7—C8	1.4047 (18)	C19—C20	1.3892 (14)
C7—H7	0.9500	C19—H19	0.9500
C8—C9	1.3636 (19)	C20—H20	0.9500
C8—H8	0.9500	N1—H1N	0.896 (12)
C9—C10	1.4207 (15)	N1—H2N	0.883 (12)
C9—H9	0.9500	O2—H2O	0.885 (13)
C10—C11	1.4162 (17)
N1—C1—O1	111.01 (9)	C12—C11—C10	121.03 (10)
N1—C1—C2	127.23 (10)	C12—C11—H11	119.5
O1—C1—C2	121.75 (9)	C10—C11—H11	119.5
C1—C2—C14	117.94 (9)	C11—C12—C13	118.93 (10)
C1—C2—C3	122.99 (9)	C11—C12—H12	120.5
C14—C2—C3	119.07 (8)	C13—C12—H12	120.5
C4—C3—C2	109.14 (8)	C4—C13—O1	123.20 (9)
C4—C3—C15	112.06 (8)	C4—C13—C12	123.35 (10)
C2—C3—C15	110.69 (8)	O1—C13—C12	113.46 (9)
C4—C3—H3	108.3	N2—C14—C2	178.35 (12)
C2—C3—H3	108.3	C20—C15—C16	118.23 (9)
C15—C3—H3	108.3	C20—C15—C3	121.06 (8)
C13—C4—C5	118.06 (9)	C16—C15—C3	120.61 (8)
C13—C4—C3	120.77 (9)	C17—C16—C15	121.23 (9)
C5—C4—C3	121.16 (9)	C17—C16—H16	119.4
C6—C5—C10	118.25 (10)	C15—C16—H16	119.4
C6—C5—C4	122.52 (10)	C16—C17—C18	119.55 (9)
C10—C5—C4	119.23 (10)	C16—C17—H17	120.2
C7—C6—C5	121.03 (11)	C18—C17—H17	120.2
C7—C6—H6	119.5	O2—C18—C19	118.08 (9)
C5—C6—H6	119.5	O2—C18—C17	122.03 (9)
C6—C7—C8	120.47 (12)	C19—C18—C17	119.90 (9)
C6—C7—H7	119.8	C18—C19—C20	119.79 (9)
C8—C7—H7	119.8	C18—C19—H19	120.1
C9—C8—C7	120.00 (11)	C20—C19—H19	120.1
C9—C8—H8	120.0	C15—C20—C19	121.29 (9)
C7—C8—H8	120.0	C15—C20—H20	119.4
C8—C9—C10	121.26 (11)	C19—C20—H20	119.4
C8—C9—H9	119.4	C1—N1—H1N	117.9 (9)
C10—C9—H9	119.4	C1—N1—H2N	119.1 (9)
C11—C10—C9	121.63 (10)	H1N—N1—H2N	122.1 (13)
C11—C10—C5	119.39 (10)	C1—O1—C13	118.57 (8)
C9—C10—C5	118.98 (11)	C18—O2—H2O	109.9 (11)
N1—C1—C2—C14	−4.87 (16)	C9—C10—C11—C12	−178.64 (10)
O1—C1—C2—C14	173.97 (9)	C5—C10—C11—C12	0.69 (16)
N1—C1—C2—C3	174.55 (9)	C10—C11—C12—C13	−0.47 (17)
O1—C1—C2—C3	−6.61 (15)	C5—C4—C13—O1	−179.02 (9)
C1—C2—C3—C4	18.81 (13)	C3—C4—C13—O1	2.51 (15)
C14—C2—C3—C4	−161.78 (9)	C5—C4—C13—C12	1.68 (15)
C1—C2—C3—C15	−104.97 (10)	C3—C4—C13—C12	−176.79 (9)
C14—C2—C3—C15	74.44 (11)	C11—C12—C13—C4	−0.76 (16)
C2—C3—C4—C13	−16.41 (12)	C11—C12—C13—O1	179.88 (9)
C15—C3—C4—C13	106.56 (10)	C4—C3—C15—C20	134.98 (10)
C2—C3—C4—C5	165.16 (8)	C2—C3—C15—C20	−102.93 (10)
C15—C3—C4—C5	−71.87 (11)	C4—C3—C15—C16	−48.65 (12)
C13—C4—C5—C6	178.20 (9)	C2—C3—C15—C16	73.44 (11)
C3—C4—C5—C6	−3.33 (14)	C20—C15—C16—C17	−0.56 (14)
C13—C4—C5—C10	−1.40 (14)	C3—C15—C16—C17	−177.04 (9)
C3—C4—C5—C10	177.07 (9)	C15—C16—C17—C18	−0.08 (15)
C10—C5—C6—C7	0.61 (15)	C16—C17—C18—O2	−179.34 (9)
C4—C5—C6—C7	−178.99 (10)	C16—C17—C18—C19	0.85 (15)
C5—C6—C7—C8	−1.03 (16)	O2—C18—C19—C20	179.21 (9)
C6—C7—C8—C9	0.84 (17)	C17—C18—C19—C20	−0.97 (16)
C7—C8—C9—C10	−0.24 (17)	C16—C15—C20—C19	0.45 (15)
C8—C9—C10—C11	179.16 (10)	C3—C15—C20—C19	176.91 (9)
C8—C9—C10—C5	−0.17 (16)	C18—C19—C20—C15	0.31 (16)
C6—C5—C10—C11	−179.35 (9)	N1—C1—O1—C13	169.17 (8)
C4—C5—C10—C11	0.26 (14)	C2—C1—O1—C13	−9.84 (14)
C6—C5—C10—C9	−0.01 (14)	C4—C13—O1—C1	12.00 (14)
C4—C5—C10—C9	179.60 (9)	C12—C13—O1—C1	−168.63 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.90 (1)	2.03 (1)	2.9191 (12)	173 (1)
O2—H2O···N2ii	0.89 (1)	1.86 (1)	2.7403 (12)	175 (2)
N1—H2N···Cg4iii	0.88 (1)	2.55 (1)	3.2340 (11)	135 (1)
C11—H11···Cg3iv	0.95	2.97	3.7610 (13)	142

Table 1

Hydrogen-bond geometry (, )

Cg3 and Cg4 are the centroids of the C5C10 and C15C20 rings, respectively.

DHA	DH	HA	D A	DHA
N1H1NO2i	0.90(1)	2.03(1)	2.9191(12)	173(1)
O2H2ON2ii	0.89(1)	1.86(1)	2.7403(12)	175(2)
N1H2N Cg4iii	0.88(1)	2.55(1)	3.2340(11)	135(1)
C11H11Cg3iv	0.95	2.97	3.7610(13)	142

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