Crystal structure of 3-amino-1-(4-meth­oxy­phen­yl)-1H-benzo[f]chromene-2-carbo­nitrile

Mohamed, S.K.; Horton, P.N.; Akkurt, M.; Younes, S.H.H.; Albayati, M.R.

doi:10.1107/S2056989015011020

organic compounds

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ISSN: 2056-9890

Volume 71| Part 7| July 2015| Pages o468-o469

doi:10.1107/S2056989015011020

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Crystal structure of 3-amino-1-(4-methoxyphenyl)-1H-benzo[f]chromene-2-carbonitrile

Shaaban K. Mohamed,^a,^b Peter N. Horton,^c Mehmet Akkurt,^d Sabry H. H. Younes ^e and Mustafa R. Albayati ^f ^*

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cSchool of Chemistry, University of Southampton, Highfield, Southampton, SO17 1BJ, England, ^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 P. C. Healy, Griffith University, Australia (Received 5 June 2015; accepted 6 June 2015; online 13 June 2015)

In the title compound, C₂₁H₁₆N₂O₂, the methoxybenzene ring is almost perpendicular to the mean plane of the naphthalene ring system, making a dihedral angle of 83.62 (5)°. The 4H-pyran ring fused with the naphthalene ring system is almost planar [maximum deviation = 0.033 (1) Å]. In the crystal, molecules are linked into inversion dimers by pairs of N—H⋯N hydrogen bonds. N—H⋯O hydrogen bonds connect the dimers, forming a helical supramolecular chain along the a-axis direction. The crystal packing also features C—H⋯π interactions.

Keywords: crystal structure; chromene compounds; benzochromene; hydrogen bonding; C—H⋯π interactions.

CCDC reference: 1405398

1. Related literature

For the biological interest of benzochromene derivatives, see: Gourdeau et al. (2004 ); Sangani et al. (2012 ); Cheng et al. (2003 ); Kamal et al. (2012 ); Denish et al. (2012 ); Nitin et al.. (2012 ); Bhat et al. (2008 ). For a similar structure, see: Akkurt et al. (2013 ).

2. Experimental

2.1. Crystal data

C₂₁H₁₆N₂O₂
M_r = 328.36
Monoclinic, I 2/a
a = 20.6017 (14) Å
b = 6.1461 (4) Å
c = 25.9689 (16) Å
β = 94.332 (4)°
V = 3278.8 (4) Å³
Z = 8
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 100 K
0.38 × 0.23 × 0.13 mm

2.2. Data collection

Rigaku AFC11 diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012 ) T_min = 0.910, T_max = 1.000
12941 measured reflections
2914 independent reflections
2832 reflections with I > 2σ(I)
R_int = 0.037

2.3. Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.116
S = 1.03
2914 reflections
236 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4/C5/C10–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2ⁱ	0.896 (18)	2.125 (18)	3.0174 (15)	173.8 (16)
N1—H1B⋯O2ⁱⁱ	0.900 (17)	2.053 (17)	2.9509 (14)	175.5 (14)
C11—H11⋯Cg2ⁱⁱⁱ	0.95	2.56	3.3913 (14)	147
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x-{\script{1\over 2}}, -y+2, z]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrystalClearSM Expert (Rigaku, 2012); cell refinement: CrystalClearSM Expert; data reduction: CrystalClearSM Expert; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1405398

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015011020/hg5445sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015011020/hg5445Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015011020/hg5445Isup3.cml

checkCIF report

Comment top

Benzopyran (Chromene) is one of the important medicinal pharmacophores found in natural compounds which generated great attention because of their interesting biological activity. The natural and synthetic chromene derivatives have important biological activities such as antivascular (Gourdeau et al., 2004), antimicrobial (Sangani et al., 2012), TNF-α inhibitor (Cheng et al., 2003), anticancer (Kamal et al., 2012), anti-HIV (Denish et al., 2012), anti-inflammatory (Nitin et al., 2012), and anticonvulsant activity (Bhat et al., 2008). Based on such findings and following to our study on synthesis of bio-active heterocyclic molecules we herein report the synthesis and crystal structure of the title compound.

Fig. 1 shows the asymmetric unit of the title compound. The methoxybenzene ring (C15–C20) is approximately perpendicular to the naphthalene ring system [C4–C13, maximum deviation = 0.040 (1) Å at atom C12] as indicated by the dihedral angle of 83.62 (5)°. The pyran ring (O1/C1–C4/C13) is almost planar [maximum deviation = -0.033 (1) Å at atom C2]. The methoxy group (C21/O2) is nearly co-planar with the attached benzene ring (C15–C20) with the torsion angle C21—O2—C18—C19 of -171.07 (11)°. The bond lengths and angles in the title compound are within normal ranges and comparable with those reported for a similar structure (Akkurt et al., 2013).

In the crystal, molecules are linked into a helical supramolecular chain along the a axis, which consist of N1—H1B···O2 hydrogen bonds that connect the dimers formed by N1—H1A···N2 hydrogen bonds, to each other (Fig. 2). The crystal packing is further stabilized by C—H···π interactions (Table 1).

Related literature top

For the biological interest of benzochromene derivatives, see: Gourdeau et al. (2004); Sangani et al. (2012); Cheng et al. (2003); Kamal et al. (2012); Denish et al. (2012); Nitin et al.. (2012); Bhat et al. (2008). For a similar structure, see: Akkurt et al. (2013).

Experimental top

An ethanolic solution of 4-methoxybenzylidenepropanedinitrile (184 mg; 1 mmol) and 2-naphthol (144 mg; 1 mmol) was refluxed with stirring for 3 h at 350 K with adding two drops of piperidine. The solid product was obtained by cooling the reaction mixture to room temperature, then it was collected by filtration, washed with cold ethanol and dried under vacuum. Colourless crystals of the title compound (M.p. 465 K) suitable for X-ray diffraction were obtained in excellent yield (87%) by recrystallization of the crude product from ethanol using the slow evaporation method.

Computing details top

Data collection: CrystalClearSM Expert (Rigaku, 2012); cell refinement: CrystalClearSM Expert (Rigaku, 2012); data reduction: CrystalClearSM Expert (Rigaku, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. View of the dimers forming by N—H···N hydrogen bonds.

3-Amino-1-(4-methoxyphenyl)-1H-benzo[f]chromene-2-carbonitrile top

Crystal data top

C₂₁H₁₆N₂O₂	F(000) = 1376
M_r = 328.36	D_x = 1.330 Mg m⁻³
Monoclinic, I2/a	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -I 2ya	Cell parameters from 15816 reflections
a = 20.6017 (14) Å	θ = 2.6–68.3°
b = 6.1461 (4) Å	µ = 0.70 mm⁻¹
c = 25.9689 (16) Å	T = 100 K
β = 94.332 (4)°	Prism, colourless
V = 3278.8 (4) Å³	0.38 × 0.23 × 0.13 mm
Z = 8

Data collection top

Rigaku AFC11 diffractometer	2914 independent reflections
Radiation source: Rotating Anode	2832 reflections with I > 2σ(I)
Detector resolution: 22.2222 pixels mm^-1	R_int = 0.037
profile data from ω–scans	θ_max = 68.2°, θ_min = 3.4°
Absorption correction: multi-scan (CrystalClearSM Expert; Rigaku, 2012)	h = −24→24
T_min = 0.910, T_max = 1.000	k = −5→7
12941 measured reflections	l = −31→24

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.041	w = 1/[σ²(F_o²) + (0.0752P)² + 2.3851P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.116	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.31 e Å⁻³
2914 reflections	Δρ_min = −0.23 e Å⁻³
236 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
0 restraints	Extinction coefficient: 0.0014 (2)

Crystal data top

C₂₁H₁₆N₂O₂	V = 3278.8 (4) Å³
M_r = 328.36	Z = 8
Monoclinic, I2/a	Cu Kα radiation
a = 20.6017 (14) Å	µ = 0.70 mm⁻¹
b = 6.1461 (4) Å	T = 100 K
c = 25.9689 (16) Å	0.38 × 0.23 × 0.13 mm
β = 94.332 (4)°

Data collection top

Rigaku AFC11 diffractometer	2914 independent reflections
Absorption correction: multi-scan (CrystalClearSM Expert; Rigaku, 2012)	2832 reflections with I > 2σ(I)
T_min = 0.910, T_max = 1.000	R_int = 0.037
12941 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.31 e Å⁻³
2914 reflections	Δρ_min = −0.23 e Å⁻³
236 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	0.46524 (4)	1.06769 (14)	0.61312 (3)	0.0180 (2)
O2	0.82346 (4)	0.82919 (15)	0.54600 (3)	0.0243 (3)
N1	0.43089 (5)	0.85280 (19)	0.54736 (4)	0.0229 (3)
N2	0.54448 (5)	0.39845 (17)	0.54907 (4)	0.0212 (3)
C1	0.47727 (6)	0.88455 (19)	0.58585 (5)	0.0171 (3)
C2	0.52947 (6)	0.75466 (19)	0.59874 (5)	0.0172 (3)
C3	0.58264 (6)	0.80882 (19)	0.64036 (4)	0.0166 (3)
C4	0.56459 (6)	1.01315 (19)	0.66861 (4)	0.0166 (3)
C5	0.60414 (6)	1.0884 (2)	0.71278 (5)	0.0184 (3)
C6	0.65975 (6)	0.9729 (2)	0.73361 (5)	0.0233 (4)
C7	0.69636 (7)	1.0479 (3)	0.77625 (5)	0.0303 (4)
C8	0.68002 (7)	1.2444 (3)	0.80039 (5)	0.0301 (4)
C9	0.62635 (6)	1.3586 (2)	0.78173 (5)	0.0245 (4)
C10	0.58687 (6)	1.2843 (2)	0.73818 (5)	0.0190 (3)
C11	0.52962 (6)	1.39706 (19)	0.71978 (5)	0.0189 (3)
C12	0.49085 (6)	1.3200 (2)	0.67886 (5)	0.0181 (3)
C13	0.50912 (6)	1.12794 (19)	0.65376 (4)	0.0164 (3)
C14	0.53658 (5)	0.5592 (2)	0.57068 (4)	0.0170 (3)
C15	0.64862 (5)	0.8191 (2)	0.61700 (4)	0.0162 (3)
C16	0.68716 (6)	0.6343 (2)	0.61775 (5)	0.0192 (3)
C17	0.74603 (6)	0.6302 (2)	0.59448 (5)	0.0204 (3)
C18	0.76660 (6)	0.8158 (2)	0.57027 (5)	0.0189 (3)
C19	0.72851 (6)	1.0035 (2)	0.56930 (5)	0.0198 (3)
C20	0.66979 (6)	1.0046 (2)	0.59208 (4)	0.0180 (3)
C21	0.85852 (6)	0.6305 (2)	0.53986 (6)	0.0306 (4)
H1A	0.4404 (8)	0.772 (3)	0.5202 (7)	0.031 (4)*
H1B	0.3976 (8)	0.948 (3)	0.5451 (6)	0.028 (4)*
H3	0.58470	0.68680	0.66590	0.0200*
H6	0.67180	0.84130	0.71770	0.0280*
H7	0.73310	0.96680	0.78970	0.0360*
H8	0.70620	1.29690	0.82940	0.0360*
H9	0.61530	1.49000	0.79820	0.0290*
H11	0.51810	1.52820	0.73620	0.0230*
H12	0.45200	1.39460	0.66740	0.0220*
H16	0.67320	0.50720	0.63450	0.0230*
H17	0.77170	0.50160	0.59520	0.0250*
H19	0.74290	1.13120	0.55290	0.0240*
H20	0.64380	1.13240	0.59070	0.0220*
H21A	0.83040	0.52570	0.52050	0.0460*
H21B	0.87210	0.57030	0.57390	0.0460*
H21C	0.89700	0.65970	0.52100	0.0460*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0168 (4)	0.0180 (4)	0.0191 (4)	0.0025 (3)	0.0012 (3)	−0.0031 (3)
O2	0.0162 (4)	0.0278 (5)	0.0297 (5)	−0.0001 (4)	0.0079 (4)	−0.0048 (4)
N1	0.0184 (5)	0.0256 (6)	0.0243 (6)	0.0045 (4)	−0.0010 (4)	−0.0081 (5)
N2	0.0229 (5)	0.0203 (6)	0.0204 (5)	0.0018 (4)	0.0015 (4)	−0.0013 (4)
C1	0.0171 (6)	0.0171 (6)	0.0176 (6)	−0.0016 (4)	0.0052 (4)	−0.0018 (4)
C2	0.0169 (6)	0.0171 (6)	0.0179 (6)	−0.0010 (5)	0.0039 (4)	−0.0010 (5)
C3	0.0166 (6)	0.0169 (6)	0.0163 (6)	−0.0003 (4)	0.0023 (4)	0.0006 (5)
C4	0.0167 (6)	0.0177 (6)	0.0159 (6)	−0.0012 (5)	0.0055 (4)	0.0013 (5)
C5	0.0188 (6)	0.0204 (6)	0.0165 (6)	−0.0013 (5)	0.0049 (5)	0.0009 (5)
C6	0.0238 (6)	0.0262 (7)	0.0199 (6)	0.0044 (5)	0.0010 (5)	−0.0027 (5)
C7	0.0255 (7)	0.0398 (8)	0.0248 (7)	0.0073 (6)	−0.0039 (5)	−0.0037 (6)
C8	0.0283 (7)	0.0398 (8)	0.0213 (6)	−0.0005 (6)	−0.0041 (5)	−0.0086 (6)
C9	0.0268 (7)	0.0261 (7)	0.0210 (6)	−0.0020 (5)	0.0045 (5)	−0.0057 (5)
C10	0.0209 (6)	0.0199 (6)	0.0170 (6)	−0.0026 (5)	0.0063 (5)	−0.0003 (5)
C11	0.0231 (6)	0.0164 (6)	0.0180 (6)	−0.0017 (5)	0.0078 (5)	−0.0003 (5)
C12	0.0183 (6)	0.0179 (6)	0.0188 (6)	0.0010 (5)	0.0062 (5)	0.0025 (5)
C13	0.0170 (6)	0.0183 (6)	0.0143 (5)	−0.0022 (4)	0.0038 (4)	0.0015 (4)
C14	0.0156 (6)	0.0197 (6)	0.0160 (6)	−0.0003 (4)	0.0024 (4)	0.0019 (5)
C15	0.0149 (6)	0.0189 (6)	0.0146 (5)	−0.0004 (4)	−0.0001 (4)	−0.0024 (4)
C16	0.0199 (6)	0.0165 (6)	0.0213 (6)	0.0000 (5)	0.0015 (5)	0.0007 (5)
C17	0.0178 (6)	0.0194 (6)	0.0240 (6)	0.0046 (5)	0.0008 (5)	−0.0031 (5)
C18	0.0139 (5)	0.0257 (6)	0.0172 (6)	−0.0013 (5)	0.0019 (4)	−0.0053 (5)
C19	0.0213 (6)	0.0181 (6)	0.0203 (6)	−0.0025 (5)	0.0031 (5)	0.0001 (5)
C20	0.0185 (6)	0.0163 (6)	0.0192 (6)	0.0022 (4)	0.0016 (4)	−0.0016 (5)
C21	0.0197 (6)	0.0321 (8)	0.0410 (8)	0.0025 (5)	0.0089 (6)	−0.0137 (6)

Geometric parameters (Å, º) top

O1—C1	1.3625 (15)	C11—C12	1.3650 (18)
O1—C13	1.3871 (14)	C12—C13	1.4132 (17)
O2—C18	1.3740 (15)	C15—C20	1.3970 (17)
O2—C21	1.4338 (15)	C15—C16	1.3851 (17)
N1—C1	1.3438 (16)	C16—C17	1.3955 (18)
N2—C14	1.1538 (16)	C17—C18	1.3843 (18)
C1—C2	1.3607 (17)	C18—C19	1.3944 (17)
N1—H1B	0.900 (17)	C19—C20	1.3862 (17)
N1—H1A	0.896 (18)	C3—H3	1.0000
C2—C14	1.4184 (17)	C6—H6	0.9500
C2—C3	1.5166 (17)	C7—H7	0.9500
C3—C4	1.5149 (16)	C8—H8	0.9500
C3—C15	1.5311 (16)	C9—H9	0.9500
C4—C13	1.3733 (17)	C11—H11	0.9500
C4—C5	1.4326 (17)	C12—H12	0.9500
C5—C10	1.4307 (18)	C16—H16	0.9500
C5—C6	1.4197 (18)	C17—H17	0.9500
C6—C7	1.3716 (19)	C19—H19	0.9500
C7—C8	1.413 (2)	C20—H20	0.9500
C8—C9	1.367 (2)	C21—H21A	0.9800
C9—C10	1.4178 (18)	C21—H21B	0.9800
C10—C11	1.4194 (18)	C21—H21C	0.9800

C1—O1—C13	118.84 (9)	C15—C16—C17	121.65 (11)
C18—O2—C21	117.01 (10)	C16—C17—C18	119.19 (11)
O1—C1—N1	111.07 (10)	O2—C18—C19	116.12 (11)
O1—C1—C2	121.89 (11)	O2—C18—C17	123.96 (11)
N1—C1—C2	127.02 (12)	C17—C18—C19	119.92 (12)
H1A—N1—H1B	121.3 (15)	C18—C19—C20	120.29 (11)
C1—N1—H1A	118.7 (11)	C15—C20—C19	120.45 (11)
C1—N1—H1B	116.7 (11)	C2—C3—H3	107.00
C1—C2—C3	124.15 (11)	C4—C3—H3	107.00
C1—C2—C14	118.75 (11)	C15—C3—H3	107.00
C3—C2—C14	117.06 (10)	C5—C6—H6	119.00
C2—C3—C4	109.67 (10)	C7—C6—H6	119.00
C4—C3—C15	114.55 (10)	C6—C7—H7	120.00
C2—C3—C15	109.98 (9)	C8—C7—H7	120.00
C5—C4—C13	118.03 (10)	C7—C8—H8	120.00
C3—C4—C5	120.65 (10)	C9—C8—H8	120.00
C3—C4—C13	121.29 (10)	C8—C9—H9	119.00
C4—C5—C6	122.51 (11)	C10—C9—H9	119.00
C4—C5—C10	119.65 (11)	C10—C11—H11	119.00
C6—C5—C10	117.83 (11)	C12—C11—H11	119.00
C5—C6—C7	121.22 (12)	C11—C12—H12	120.00
C6—C7—C8	120.70 (13)	C13—C12—H12	120.00
C7—C8—C9	119.67 (13)	C15—C16—H16	119.00
C8—C9—C10	121.15 (12)	C17—C16—H16	119.00
C5—C10—C9	119.42 (11)	C16—C17—H17	120.00
C5—C10—C11	119.01 (11)	C18—C17—H17	120.00
C9—C10—C11	121.56 (11)	C18—C19—H19	120.00
C10—C11—C12	121.01 (11)	C20—C19—H19	120.00
C11—C12—C13	119.23 (11)	C15—C20—H20	120.00
C4—C13—C12	123.00 (11)	C19—C20—H20	120.00
O1—C13—C12	113.14 (10)	O2—C21—H21A	109.00
O1—C13—C4	123.86 (10)	O2—C21—H21B	109.00
N2—C14—C2	177.37 (12)	O2—C21—H21C	109.00
C3—C15—C16	119.06 (10)	H21A—C21—H21B	109.00
C3—C15—C20	122.33 (10)	H21A—C21—H21C	109.00
C16—C15—C20	118.49 (10)	H21B—C21—H21C	109.00

C13—O1—C1—N1	−178.67 (10)	C5—C4—C13—O1	−177.22 (10)
C13—O1—C1—C2	2.86 (17)	C5—C4—C13—C12	2.37 (18)
C1—O1—C13—C4	−0.19 (16)	C4—C5—C6—C7	−179.38 (13)
C1—O1—C13—C12	−179.81 (10)	C10—C5—C6—C7	−0.91 (19)
C21—O2—C18—C17	8.50 (17)	C4—C5—C10—C9	−179.71 (11)
C21—O2—C18—C19	−171.07 (11)	C4—C5—C10—C11	1.72 (18)
O1—C1—C2—C3	−6.34 (19)	C6—C5—C10—C9	1.78 (18)
O1—C1—C2—C14	175.95 (11)	C6—C5—C10—C11	−176.80 (12)
N1—C1—C2—C3	175.45 (12)	C5—C6—C7—C8	−0.7 (2)
N1—C1—C2—C14	−2.3 (2)	C6—C7—C8—C9	1.4 (2)
C1—C2—C3—C4	6.28 (16)	C7—C8—C9—C10	−0.5 (2)
C1—C2—C3—C15	−120.55 (13)	C8—C9—C10—C5	−1.10 (19)
C14—C2—C3—C4	−175.97 (10)	C8—C9—C10—C11	177.44 (13)
C14—C2—C3—C15	57.20 (14)	C5—C10—C11—C12	0.73 (19)
C2—C3—C4—C5	174.52 (11)	C9—C10—C11—C12	−177.82 (12)
C2—C3—C4—C13	−3.53 (15)	C10—C11—C12—C13	−1.63 (19)
C15—C3—C4—C5	−61.27 (14)	C11—C12—C13—O1	179.67 (11)
C15—C3—C4—C13	120.68 (12)	C11—C12—C13—C4	0.03 (19)
C2—C3—C15—C16	−93.24 (12)	C3—C15—C16—C17	176.32 (11)
C2—C3—C15—C20	82.78 (13)	C20—C15—C16—C17	0.14 (18)
C4—C3—C15—C16	142.72 (11)	C3—C15—C20—C19	−176.89 (10)
C4—C3—C15—C20	−41.26 (14)	C16—C15—C20—C19	−0.85 (17)
C3—C4—C5—C6	−2.87 (18)	C15—C16—C17—C18	0.34 (19)
C3—C4—C5—C10	178.69 (11)	C16—C17—C18—O2	−179.67 (11)
C13—C4—C5—C6	175.25 (12)	C16—C17—C18—C19	−0.12 (19)
C13—C4—C5—C10	−3.20 (17)	O2—C18—C19—C20	179.00 (11)
C3—C4—C13—O1	0.88 (17)	C17—C18—C19—C20	−0.59 (19)
C3—C4—C13—C12	−179.53 (11)	C18—C19—C20—C15	1.08 (18)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C4/C5/C10–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.896 (18)	2.125 (18)	3.0174 (15)	173.8 (16)
N1—H1B···O2ⁱⁱ	0.900 (17)	2.053 (17)	2.9509 (14)	175.5 (14)
C11—H11···Cg2ⁱⁱⁱ	0.95	2.56	3.3913 (14)	147

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1/2, −y+2, z; (iii) −x+1, y+1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C4/C5/C10–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2ⁱ	0.896 (18)	2.125 (18)	3.0174 (15)	173.8 (16)
N1—H1B···O2ⁱⁱ	0.900 (17)	2.053 (17)	2.9509 (14)	175.5 (14)
C11—H11···Cg2ⁱⁱⁱ	0.95	2.56	3.3913 (14)	147

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1/2, −y+2, z; (iii) −x+1, y+1/2, −z+3/2.

Acknowledgements

The authors would like to express their thanks to the National Crystallography Service (NCS), Southampton, UK, for providing the X-ray data.

References

Akkurt, M., Kennedy, A. R., Mohamed, S. K., Younes, S. H. H. & Miller, G. J. (2013). Acta Cryst. E69, o401. CSD CrossRef IUCr Journals Google Scholar
Bhat, M. A., Siddiqui, N. & Khan, S. A. (2008). Acta Pol. Pharm. 65, 235–239. Web of Science PubMed CAS Google Scholar
Cheng, J., Ishikawa, A., Ono, Y., Arrhenius, T. & Nadzan, A. (2003). Bioorg. Med. Chem. Lett. 13, 3647–3650. Web of Science CrossRef PubMed CAS Google Scholar
Denish, C. K., Hetal, K. P. & Nilesh, K. G. (2012). Asian J. Biochem. Pharm. Res. 2, 126–130. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gourdeau, H., Leblond, L., Hamelin, B., Desputeau, C., Dong, K., Kianicka, I., Custeau, D., Boudreau, C., Geerts, L., Cai, S. X., Drewe, J., Labrecque, D., Kasibhatla, S. & Tseng, B. (2004). Mol. Cancer Ther. 3, 1375–1384. Web of Science PubMed CAS Google Scholar
Kamal, A. M., Abd El-all, E. K. H., Elshemy, H. A. & Kandeel, M. M. (2012). Int. J. Pharm. Res. Dev. 4, 310–322. Google Scholar
Nitin, K., Sushil, K., Himanshu, G. & Sharma, P. K. (2012). World Res. J. Biochem. 1, 1–5. Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Rigaku (2012). CrystalClearSM Expert. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sangani, C. B., Shah, N. M., Patel, M. P. & Patel, R. G. (2012). J. Serb. Chem. Soc. 77, 1165–1174. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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Volume 71| Part 7| July 2015| Pages o468-o469

doi:10.1107/S2056989015011020

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

Crystal structure of 3-amino-1-(4-meth­­oxy­phen­yl)-1H-benzo[f]chromene-2-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 3-amino-1-(4-methoxyphenyl)-1H-benzo[f]chromene-2-carbonitrile