Crystal structure of 2-amino-4-(4-meth-oxy-phen-yl)-4H-benzo[g]chromene-3-carbo-nitrile.

In the title compound, C21H16N2O2, the naphthalene fragment is twisted slightly, as indicated by the dihedral angle of 3.2 (2)° between the two six-membered rings. The pendant 4-meth-oxy-phenyl ring makes a dihedral angle of 86.08 (6)° with the central six-membered ring of the 4H-benzo[g]chromene ring system. In the crystal, mol-ecules are linked by pairs of N-H⋯N hydrogen bonds, forming inversion dimers which are linked into chains propagating in the b-axis direction by N-H⋯O hydrogen bonds.

Related literature

For the chemical and pharmacological properties of 4H-chromene and fused 4H-chromene derivatives, see: Bonsignore et al. (1993 ▸); Martínez-Grau & Marco (1997 ▸); Abd-El-Aziz et al. (2007 ▸); Sabry et al. (2011 ▸). For the synthesis and biological activities of 2-amino-3-cyano-4H-chromene derivatives, see: Kemnitzer et al. (2005 ▸); Patil et al. (2012 ▸); Kumar et al. (2009 ▸).

Experimental

Crystal data

C21H16N2O2

M = 328.36

Triclinic,

a = 6.3833 (2) Å

b = 10.6009 (3) Å

c = 13.0915 (4) Å

α = 108.823 (2)°

β = 95.906 (2)°

γ = 97.467 (2)°

V = 821.44 (4) Å3

Z = 2

Cu Kα radiation

μ = 0.69 mm−1

T = 150 K

0.26 × 0.20 × 0.02 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2015 ▸) T min = 0.78, T max = 0.99

6215 measured reflections

3039 independent reflections

2074 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.151

S = 1.03

3039 reflections

235 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2015 ▸); cell refinement: SAINT (Bruker, 2015 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901502280X/su5248sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901502280X/su5248Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S205698901502280X/su5248Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S205698901502280X/su5248fig1.tif

The mol­ecular structure of the title compound with the labeling scheme and 50% probability displacement ellipsoids.

Click here for additional data file.

c . DOI: 10.1107/S205698901502280X/su5248fig2.tif

View along the c axis of one hydrogen-bonded layer. The N—H⋯N and N—H⋯O hydrogen bonds (see Table 1) are shown as blue and purple dotted lines, respectively.

Click here for additional data file.

. DOI: 10.1107/S205698901502280X/su5248fig3.tif

Crystal packing viewed along the c axis, with the N—H⋯N and N—H⋯O hydrogen bonds (see Table 1) shown as blue and purple dotted lines, respectively.

CCDC reference: 1439459

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

C21H16N2O2	Z = 2
Mr = 328.36	F(000) = 344
Triclinic, P1	Dx = 1.328 Mg m−3
a = 6.3833 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.6009 (3) Å	Cell parameters from 3044 reflections
c = 13.0915 (4) Å	θ = 3.6–72.4°
α = 108.823 (2)°	µ = 0.69 mm−1
β = 95.906 (2)°	T = 150 K
γ = 97.467 (2)°	Plate, colourless
V = 821.44 (4) Å3	0.26 × 0.20 × 0.02 mm

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3039 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2074 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.048
Detector resolution: 10.4167 pixels mm-1	θmax = 72.4°, θmin = 3.6°
ω scans	h = −7→6
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −12→13
Tmin = 0.78, Tmax = 0.99	l = −16→16
6215 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)] = 0.057	Hydrogen site location: mixed
wR(F2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0739P)2 + 0.065P] where P = (Fo2 + 2Fc2)/3
3039 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.22 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 − 1.00 Å). All were included as riding contributions with isotropic displacement parameters 1.2 − 1.5 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
O1	0.3785 (2)	0.96970 (14)	0.76705 (13)	0.0403 (4)
O2	0.3737 (3)	0.29798 (15)	0.88255 (14)	0.0498 (5)
N1	1.0346 (3)	0.8671 (2)	0.90170 (17)	0.0471 (5)
N2	0.6393 (3)	1.08806 (19)	0.90280 (19)	0.0475 (6)
H2A	0.741 (5)	1.101 (3)	0.966 (2)	0.060 (8)*
H2B	0.559 (5)	1.159 (3)	0.909 (2)	0.064 (8)*
C1	0.5666 (3)	0.9677 (2)	0.82491 (19)	0.0368 (5)
C2	0.6619 (3)	0.8565 (2)	0.80085 (18)	0.0357 (5)
C3	0.5665 (3)	0.7233 (2)	0.71189 (18)	0.0369 (5)
H3	0.6756	0.6971	0.6629	0.044*
C4	0.3733 (3)	0.7425 (2)	0.64460 (18)	0.0369 (5)
C5	0.2723 (4)	0.6386 (2)	0.5477 (2)	0.0438 (6)
H5	0.3325	0.5587	0.5229	0.053*
C6	0.0909 (4)	0.6488 (2)	0.4883 (2)	0.0451 (6)
H6	0.0290	0.5778	0.4223	0.054*
C7	−0.0054 (4)	0.7651 (2)	0.52499 (19)	0.0395 (5)
C8	−0.2030 (4)	0.7755 (3)	0.4698 (2)	0.0483 (6)
H8	−0.2732	0.7031	0.4063	0.058*
C9	−0.2917 (4)	0.8878 (3)	0.5073 (2)	0.0527 (7)
H9	−0.4237	0.8935	0.4697	0.063*
C10	−0.1911 (4)	0.9956 (3)	0.6005 (2)	0.0512 (6)
H10	−0.2559	1.0735	0.6256	0.061*
C11	−0.0004 (4)	0.9904 (2)	0.6562 (2)	0.0437 (6)
H11	0.0674	1.0646	0.7189	0.052*
C12	0.0955 (3)	0.8731 (2)	0.61949 (19)	0.0372 (5)
C13	0.2878 (3)	0.8580 (2)	0.67621 (18)	0.0356 (5)
C14	0.8674 (4)	0.8653 (2)	0.85785 (19)	0.0387 (5)
C15	0.5109 (3)	0.6109 (2)	0.75824 (18)	0.0353 (5)
C16	0.3363 (4)	0.6046 (2)	0.8117 (2)	0.0414 (6)
H16	0.2487	0.6720	0.8190	0.050*
C17	0.2843 (4)	0.5033 (2)	0.8551 (2)	0.0438 (6)
H17	0.1631	0.5017	0.8914	0.053*
C18	0.4117 (4)	0.4042 (2)	0.84493 (19)	0.0395 (5)
C19	0.5888 (4)	0.4095 (2)	0.79246 (19)	0.0417 (6)
H19	0.6772	0.3426	0.7858	0.050*
C20	0.6375 (4)	0.5111 (2)	0.74989 (19)	0.0400 (5)
H20	0.7595	0.5132	0.7142	0.048*
C21	0.1919 (5)	0.2878 (3)	0.9351 (2)	0.0562 (7)
H21A	0.2068	0.3672	1.0013	0.084*
H21B	0.1803	0.2057	0.9547	0.084*
H21C	0.0631	0.2833	0.8855	0.084*

	U11	U22	U33	U12	U13	U23
O1	0.0357 (8)	0.0340 (8)	0.0500 (10)	0.0045 (6)	−0.0064 (7)	0.0171 (7)
O2	0.0608 (11)	0.0361 (8)	0.0593 (11)	0.0072 (7)	0.0046 (9)	0.0271 (8)
N1	0.0425 (12)	0.0469 (11)	0.0494 (13)	0.0127 (9)	−0.0028 (10)	0.0141 (10)
N2	0.0478 (13)	0.0318 (10)	0.0568 (14)	0.0053 (8)	−0.0132 (10)	0.0138 (10)
C1	0.0327 (12)	0.0353 (11)	0.0452 (13)	0.0006 (8)	−0.0021 (10)	0.0221 (10)
C2	0.0317 (12)	0.0361 (11)	0.0414 (13)	0.0037 (8)	0.0003 (9)	0.0183 (10)
C3	0.0355 (12)	0.0365 (11)	0.0411 (13)	0.0061 (9)	0.0043 (10)	0.0169 (10)
C4	0.0357 (12)	0.0369 (11)	0.0407 (13)	0.0021 (9)	0.0034 (9)	0.0190 (10)
C5	0.0462 (14)	0.0405 (12)	0.0448 (14)	0.0063 (10)	0.0045 (11)	0.0159 (11)
C6	0.0452 (14)	0.0477 (13)	0.0397 (13)	−0.0015 (10)	−0.0010 (11)	0.0173 (11)
C7	0.0363 (12)	0.0440 (12)	0.0425 (13)	−0.0015 (9)	0.0013 (10)	0.0252 (11)
C8	0.0405 (14)	0.0583 (15)	0.0473 (15)	−0.0045 (11)	−0.0047 (11)	0.0282 (12)
C9	0.0385 (14)	0.0650 (16)	0.0605 (17)	0.0047 (11)	−0.0042 (12)	0.0349 (14)
C10	0.0418 (14)	0.0567 (15)	0.0630 (17)	0.0120 (11)	0.0006 (12)	0.0320 (14)
C11	0.0429 (13)	0.0421 (12)	0.0507 (14)	0.0055 (10)	0.0009 (11)	0.0246 (11)
C12	0.0340 (12)	0.0415 (12)	0.0420 (13)	0.0010 (9)	0.0025 (10)	0.0254 (10)
C13	0.0344 (12)	0.0351 (11)	0.0389 (12)	−0.0012 (8)	0.0003 (9)	0.0191 (10)
C14	0.0416 (14)	0.0333 (11)	0.0424 (13)	0.0069 (9)	0.0037 (10)	0.0152 (10)
C15	0.0386 (12)	0.0305 (10)	0.0372 (12)	0.0071 (8)	0.0010 (9)	0.0130 (9)
C16	0.0448 (14)	0.0347 (11)	0.0521 (15)	0.0147 (9)	0.0132 (11)	0.0199 (11)
C17	0.0476 (14)	0.0364 (12)	0.0522 (15)	0.0098 (10)	0.0119 (11)	0.0195 (11)
C18	0.0495 (14)	0.0282 (10)	0.0398 (13)	0.0029 (9)	−0.0034 (10)	0.0148 (10)
C19	0.0495 (14)	0.0322 (11)	0.0450 (14)	0.0134 (9)	0.0011 (11)	0.0147 (10)
C20	0.0381 (13)	0.0388 (12)	0.0429 (13)	0.0090 (9)	0.0045 (10)	0.0131 (10)
C21	0.0716 (18)	0.0427 (13)	0.0585 (17)	0.0007 (12)	0.0089 (14)	0.0269 (13)

O1—C1	1.359 (3)	C8—C9	1.355 (4)
O1—C13	1.387 (3)	C8—H8	0.9500
O2—C18	1.372 (3)	C9—C10	1.399 (4)
O2—C21	1.418 (3)	C9—H9	0.9500
N1—C14	1.154 (3)	C10—C11	1.370 (3)
N2—C1	1.339 (3)	C10—H10	0.9500
N2—H2A	0.96 (3)	C11—C12	1.423 (3)
N2—H2B	0.95 (3)	C11—H11	0.9500
C1—C2	1.359 (3)	C12—C13	1.422 (3)
C2—C14	1.417 (3)	C15—C16	1.381 (3)
C2—C3	1.513 (3)	C15—C20	1.396 (3)
C3—C4	1.516 (3)	C16—C17	1.387 (3)
C3—C15	1.522 (3)	C16—H16	0.9500
C3—H3	1.0000	C17—C18	1.391 (3)
C4—C13	1.365 (3)	C17—H17	0.9500
C4—C5	1.409 (3)	C18—C19	1.386 (3)
C5—C6	1.363 (3)	C19—C20	1.380 (3)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.415 (3)	C20—H20	0.9500
C6—H6	0.9500	C21—H21A	0.9800
C7—C12	1.409 (3)	C21—H21B	0.9800
C7—C8	1.423 (3)	C21—H21C	0.9800
C1—O1—C13	119.06 (17)	C11—C10—H10	119.6
C18—O2—C21	117.97 (18)	C9—C10—H10	119.6
C1—N2—H2A	123.6 (16)	C10—C11—C12	119.6 (2)
C1—N2—H2B	119.0 (17)	C10—C11—H11	120.2
H2A—N2—H2B	115 (2)	C12—C11—H11	120.2
N2—C1—C2	127.4 (2)	C7—C12—C13	118.0 (2)
N2—C1—O1	110.53 (18)	C7—C12—C11	119.3 (2)
C2—C1—O1	122.1 (2)	C13—C12—C11	122.6 (2)
C1—C2—C14	119.1 (2)	C4—C13—O1	123.04 (19)
C1—C2—C3	123.89 (19)	C4—C13—C12	122.7 (2)
C14—C2—C3	116.96 (18)	O1—C13—C12	114.30 (18)
C2—C3—C4	109.13 (17)	N1—C14—C2	177.3 (2)
C2—C3—C15	111.84 (18)	C16—C15—C20	117.4 (2)
C4—C3—C15	111.76 (18)	C16—C15—C3	121.60 (18)
C2—C3—H3	108.0	C20—C15—C3	121.0 (2)
C4—C3—H3	108.0	C15—C16—C17	122.3 (2)
C15—C3—H3	108.0	C15—C16—H16	118.8
C13—C4—C5	117.7 (2)	C17—C16—H16	118.8
C13—C4—C3	121.9 (2)	C16—C17—C18	119.3 (2)
C5—C4—C3	120.39 (19)	C16—C17—H17	120.4
C6—C5—C4	122.1 (2)	C18—C17—H17	120.4
C6—C5—H5	118.9	O2—C18—C19	116.25 (19)
C4—C5—H5	118.9	O2—C18—C17	124.5 (2)
C5—C6—C7	120.1 (2)	C19—C18—C17	119.3 (2)
C5—C6—H6	120.0	C20—C19—C18	120.5 (2)
C7—C6—H6	120.0	C20—C19—H19	119.8
C12—C7—C6	119.2 (2)	C18—C19—H19	119.8
C12—C7—C8	118.9 (2)	C19—C20—C15	121.3 (2)
C6—C7—C8	121.8 (2)	C19—C20—H20	119.4
C9—C8—C7	120.4 (2)	C15—C20—H20	119.4
C9—C8—H8	119.8	O2—C21—H21A	109.5
C7—C8—H8	119.8	O2—C21—H21B	109.5
C8—C9—C10	120.8 (2)	H21A—C21—H21B	109.5
C8—C9—H9	119.6	O2—C21—H21C	109.5
C10—C9—H9	119.6	H21A—C21—H21C	109.5
C11—C10—C9	120.9 (2)	H21B—C21—H21C	109.5
C13—O1—C1—N2	174.13 (19)	C10—C11—C12—C7	1.2 (3)
C13—O1—C1—C2	−4.3 (3)	C10—C11—C12—C13	−176.9 (2)
N2—C1—C2—C14	−4.0 (4)	C5—C4—C13—O1	−176.9 (2)
O1—C1—C2—C14	174.2 (2)	C3—C4—C13—O1	4.8 (3)
N2—C1—C2—C3	179.2 (2)	C5—C4—C13—C12	4.2 (3)
O1—C1—C2—C3	−2.6 (3)	C3—C4—C13—C12	−174.2 (2)
C1—C2—C3—C4	9.3 (3)	C1—O1—C13—C4	3.3 (3)
C14—C2—C3—C4	−167.6 (2)	C1—O1—C13—C12	−177.71 (19)
C1—C2—C3—C15	−114.9 (2)	C7—C12—C13—C4	−2.0 (3)
C14—C2—C3—C15	68.2 (3)	C11—C12—C13—C4	176.1 (2)
C2—C3—C4—C13	−10.2 (3)	C7—C12—C13—O1	178.94 (18)
C15—C3—C4—C13	114.1 (2)	C11—C12—C13—O1	−2.9 (3)
C2—C3—C4—C5	171.5 (2)	C2—C3—C15—C16	74.0 (3)
C15—C3—C4—C5	−64.3 (3)	C4—C3—C15—C16	−48.7 (3)
C13—C4—C5—C6	−2.3 (3)	C2—C3—C15—C20	−104.9 (2)
C3—C4—C5—C6	176.1 (2)	C4—C3—C15—C20	132.4 (2)
C4—C5—C6—C7	−1.7 (4)	C20—C15—C16—C17	−0.6 (3)
C5—C6—C7—C12	3.9 (3)	C3—C15—C16—C17	−179.5 (2)
C5—C6—C7—C8	−175.3 (2)	C15—C16—C17—C18	0.0 (4)
C12—C7—C8—C9	0.4 (3)	C21—O2—C18—C19	−178.9 (2)
C6—C7—C8—C9	179.6 (2)	C21—O2—C18—C17	0.3 (3)
C7—C8—C9—C10	0.1 (4)	C16—C17—C18—O2	−178.6 (2)
C8—C9—C10—C11	0.1 (4)	C16—C17—C18—C19	0.6 (3)
C9—C10—C11—C12	−0.8 (4)	O2—C18—C19—C20	178.7 (2)
C6—C7—C12—C13	−2.1 (3)	C17—C18—C19—C20	−0.6 (3)
C8—C7—C12—C13	177.1 (2)	C18—C19—C20—C15	0.0 (3)
C6—C7—C12—C11	179.7 (2)	C16—C15—C20—C19	0.6 (3)
C8—C7—C12—C11	−1.1 (3)	C3—C15—C20—C19	179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.96 (3)	2.03 (3)	2.995 (3)	178 (3)
N2—H2B···O2ii	0.95 (3)	2.10 (3)	3.028 (3)	166 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.96 (3)	2.03 (3)	2.995 (3)	178 (3)
N2—H2B⋯O2ii	0.95 (3)	2.10 (3)	3.028 (3)	166 (2)

Symmetry codes: (i) ; (ii) .