Crystal structure of 2-amino-4-(4-meth­oxy­phen­yl)-4H-benzo[g]chromene-3-carbo­nitrile

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Younes, S.H.H.; Albayati, M.R.

doi:10.1107/S205698901502280X

organic compounds

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ISSN: 2056-9890

Volume 71| Part 12| December 2015| Pages o1017-o1018

https://doi.org/10.1107/S205698901502280X

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Crystal structure of 2-amino-4-(4-methoxyphenyl)-4H-benzo[g]chromene-3-carbonitrile

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Sabry H. H. Younes ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 20 November 2015; accepted 28 November 2015; online 6 December 2015)

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-methoxyphenyl 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, molecules 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.

Keywords: crystal structure; chromenes; benzopyrans; 2-amino-3-cyano-4H-chromene derivatives; 4H-chromene and fused 4H-chromene derivatives; hydrogen bonding.

CCDC reference: 1439459

1. 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 ).

2. Experimental

2.1. Crystal data

C₂₁H₁₆N₂O₂
M_r = 328.36
Triclinic, $[P \overline 1]$
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.151
S = 1.03
3039 reflections
235 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻³

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) -x+2, -y+2, -z+2; (ii) x, y+1, z.

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 ).

Supporting information

CCDC reference: 1439459

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S205698901502280X/su5248sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901502280X/su5248Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698901502280X/su5248Isup3.cml

checkCIF report

Structural commentary top

Fused benzo-4H-pyran, namely, 4H-chromene moiety, is the key building block of many oxygen-containing heterocyclic natural products whose pharmacological and biological activity such as anti-tumor, anti-oxidant, anti-bacterial, anti-viral, anti-fungal, hypotensive, anti-coagulant, anti-leishmanial, diuretic, and anti-allergenic activities (Bonsignore et al., 1993; Martínez-Grau & Marco, 1997; Abd-El-Aziz et al., 2007; Sabry et al., 2011). Moreover, 2-amino-3-cyano-4H-chromene derivatives have been also used as anti-cancers, inhibitors of insulin-regulated aminopeptidase (IRAP) for enhancing memory and learning functions and anti-bacterial agents (Kemnitzer et al., 2005; Patil et al., 2012; Kumar et al., 2009). In continuation of our interest in the chemical and pharmacological properties of 4H-chromene and fused 4H-chromene derivatives, we herein report on the synthesis and crystal structure of the title compound.

In the title compound, Fig. 1, the naphthalene fragment is slightly twisted as indicated by the dihedral angle of 3.2 (2)° between the two 6-membered rings. The pendant 4-methoxyphenyl ring makes a dihedral angle of 86.08 (6)° with the (C4—C7/C12/C13) ring. The heterocyclic ring (O1/C1—C4/C13) can best be described as having an envelope conformation, with atom C3 as the flap, and with pucking parameters of Q = 0.099 (2) Å, θ = 109.8 (12)° and φ = 6.5 (14)°.

In the crystal, pairwise N2—H2A···N1ⁱ hydrogen bonds form inversion dimers which are linked into chains running along the b axis direction (Fig. 2 and Table 1). The overall packing of these units in the crystal is illustrated in Fig. 3.

Synthesis and crystallization top

To a solution of 4-methoxybenzylidene-malononitrile (1 mmol, 180 mg) in 10 ml of ethanol was added 4- 1-naphthol (1 mmol, 144 mg) in the presence of few catalytic drops of piperedine and the temperature was adjusted at 353 K for 1 h. A solid product was obtained on cooling, collected by filtration and recrystallized from ethanol to afford colorless plate-like crystals suitable for X-ray diffraction analysis.

Refinement top

The NH₂ H-atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were placed in calculated positions (C—H = 0.95 - 1.00 Å) and included as riding contributions with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq(C) for other H atoms.

Related literature top

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).

Structure description top

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).

Synthesis and crystallization top

Refinement details top

Computing details top

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); 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).

Figures top

	Fig. 1. The molecular structure of the title compound with the labeling scheme and 50% probability displacement ellipsoids.
	Fig. 2. 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.
	Fig. 3. 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.

2-Amino-4-(4-methoxyphenyl)-4H-benzo[g]chromene-3-carbonitrile top

Crystal data top

C₂₁H₁₆N₂O₂	Z = 2
M_r = 328.36	F(000) = 344
Triclinic, P1	D_x = 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

Data collection top

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	R_int = 0.048
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.4°, θ_min = 3.6°
ω scans	h = −7→6
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −12→13
T_min = 0.78, T_max = 0.99	l = −16→16
6215 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)] = 0.057	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(F_o²) + (0.0739P)² + 0.065P] where P = (F_o² + 2F_c²)/3
3039 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₁H₁₆N₂O₂	γ = 97.467 (2)°
M_r = 328.36	V = 821.44 (4) Å³
Triclinic, P1	Z = 2
a = 6.3833 (2) Å	Cu Kα radiation
b = 10.6009 (3) Å	µ = 0.69 mm⁻¹
c = 13.0915 (4) Å	T = 150 K
α = 108.823 (2)°	0.26 × 0.20 × 0.02 mm
β = 95.906 (2)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3039 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2015)	2074 reflections with I > 2σ(I)
T_min = 0.78, T_max = 0.99	R_int = 0.048
6215 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.18 e Å⁻³
3039 reflections	Δρ_min = −0.22 e Å⁻³
235 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+2, −z+2; (ii) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y+2, −z+2; (ii) x, y+1, z.

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

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Volume 71| Part 12| December 2015| Pages o1017-o1018

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

Crystal structure of 2-amino-4-(4-meth­­oxy­phen­yl)-4H-benzo[g]chromene-3-carbo­nitrile

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 2-amino-4-(4-methoxyphenyl)-4H-benzo[g]chromene-3-carbonitrile