Crystal structure of 2-oxo-N′-phenyl-2H-chromene-3-carbohydrazide

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

doi:10.1107/S2056989015022495

organic compounds

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Volume 71| Part 12| December 2015| Pages o1005-o1006

https://doi.org/10.1107/S2056989015022495

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Crystal structure of 2-oxo-N′-phenyl-2H-chromene-3-carbohydrazide

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 K. Fejfarova, Institute of Macromolecular Chemistry, AS CR, v.v.i, Czech Republic (Received 20 November 2015; accepted 24 November 2015; online 28 November 2015)

In the title compound, C₁₆H₁₂N₂O₃, the 2H-chromene moiety is essentially planar, with an r.m.s. deviation of the nine constituent atoms from the mean plane of 0.0093 Å, and makes a dihedral angle of 76.84 (3)° with the pendant phenyl ring. An intramolecular N—H⋯O hydrogen bond helps to determine the conformation of the side chain. In the crystal, N—H⋯O and N—H⋯N hydrogen bonds link the molecules, forming [100] chains.

Keywords: crystal structure; coumarins; bio-activity; coumarin scaffold compounds.

CCDC reference: 1438684

1. Related literature

For synthesis and bio-activity of coumarin scaffold compounds, see: Shivashankar et al. (2008a ,b , 2009 ); Bansal et al. (2013 ); Jacquot et al. (2007 ); Bhavsar et al. (2011 ).

2. Experimental

2.1. Crystal data

C₁₆H₁₂N₂O₃
M_r = 280.28
Triclinic, $[P \overline 1]$
a = 6.6508 (2) Å
b = 8.3906 (3) Å
c = 11.6388 (4) Å
α = 96.504 (2)°
β = 95.614 (2)°
γ = 94.757 (2)°
V = 639.31 (4) Å³
Z = 2
Cu Kα radiation
μ = 0.85 mm⁻¹
T = 150 K
0.19 × 0.13 × 0.05 mm

2.2. Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2015 ) T_min = 0.88, T_max = 0.96
4865 measured reflections
2371 independent reflections
2121 reflections with I > 2σ(I)
R_int = 0.023

2.3. Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.107
S = 1.06
2371 reflections
199 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2ⁱ	0.896 (18)	2.327 (18)	3.0498 (14)	137.7 (15)
N1—H1N⋯O2	0.896 (18)	2.112 (18)	2.7544 (13)	127.8 (15)
N2—H2N⋯O2ⁱⁱ	0.911 (17)	2.243 (17)	3.1358 (14)	166.3 (14)
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x-1, y, 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: 1438684

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015022495/ff2144sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015022495/ff2144Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989015022495/ff2144Isup3.cml

checkCIF report

Comment top

Coumarins are known to be biologically versatile compounds possessing several biological properties. Numerous research reports have indicated the coumarin nucleus as a potential candidate for development of anti-inflammatory (Shivashankar et al., 2008a,b; Bansal et al., 2013), antibacterial (Shivashankar et al., 2008b), antifungal (Shivashankar et al., 2009), anti-cancer (Jacquot et al., 2007) and anti-HIV (Bhavsar et al., 2011) agents. In light of such facts, we report in this study the synthesis and crystal structure of the title compound.

The 2H-chromene moiety is essentially planar with an r.m.s. deviation of the nine constituent atoms from the mean plane of 0.0093 Å. The dihedral angle between this plane and that of the pendant phenyl ring is 76.84 (3)°. The conformation of the hydrazide side-chain is partially determined by an intramolecular N1—H1N···O2 hydrogen bond (Fig. 1 and Table 1). The packing is assisted by intermolecular N2—H2N···O2ⁱ (i: x - 1, y, z) and N1—H1N···N2ⁱⁱ (ii: -x + 1, -y + 1, -z) hydrogen bonds (Fig. 2 and Table 1).

Related literature top

For synthesis and bio-activity of coumarin scaffold compounds, see: Shivashankar et al. (2008a,b, 2009); Bansal et al. (2013); Jacquot et al. (2007); Bhavsar et al. (2011).

Experimental top

The title compound was obtained as an unexpected product from the reaction of 1-phenylpyrazolidine-3,5-dione (176 mg, 1 mmol), 2-hydroxybenzaldehyde (122 mg, 1 mmol) and o-toluidine (107 mg, 1 mmol). The reaction mixture was refluxed in 20 mL ethanol and monitored by TLC till completion. On cooling, the solid product was deposited, filtered off under vacuum and recrystallized from ethanol to afford colourless crystals in a sufficient quality for x-ray diffraction. Mp 471-473 K.

Structure description top

For synthesis and bio-activity of coumarin scaffold compounds, see: Shivashankar et al. (2008a,b, 2009); Bansal et al. (2013); Jacquot et al. (2007); Bhavsar et al. (2011).

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 title molecule with labeling scheme and 50% probability ellipsoids. The intramolecular N—H···O hydrogen bond is shown by a dotted line.
	Fig. 2. Packing viewed towards (110) with intermolecular N—H···O and N—H···N hydrogen bonds shown, respectively, as blue and purple dotted lines.

2-Oxo-N'-phenyl-2H-chromene-3-carbohydrazide top

Crystal data top

C₁₆H₁₂N₂O₃	Z = 2
M_r = 280.28	F(000) = 292
Triclinic, P1	D_x = 1.456 Mg m⁻³
a = 6.6508 (2) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.3906 (3) Å	Cell parameters from 3784 reflections
c = 11.6388 (4) Å	θ = 3.9–72.2°
α = 96.504 (2)°	µ = 0.85 mm⁻¹
β = 95.614 (2)°	T = 150 K
γ = 94.757 (2)°	Tablet, colourless
V = 639.31 (4) Å³	0.19 × 0.13 × 0.05 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2371 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2121 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.023
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.3°, θ_min = 3.9°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −9→10
T_min = 0.88, T_max = 0.96	l = −14→14
4865 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0632P)² + 0.1234P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2371 reflections	Δρ_max = 0.22 e Å⁻³
199 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0129 (16)

Crystal data top

C₁₆H₁₂N₂O₃	γ = 94.757 (2)°
M_r = 280.28	V = 639.31 (4) Å³
Triclinic, P1	Z = 2
a = 6.6508 (2) Å	Cu Kα radiation
b = 8.3906 (3) Å	µ = 0.85 mm⁻¹
c = 11.6388 (4) Å	T = 150 K
α = 96.504 (2)°	0.19 × 0.13 × 0.05 mm
β = 95.614 (2)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2371 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2015)	2121 reflections with I > 2σ(I)
T_min = 0.88, T_max = 0.96	R_int = 0.023
4865 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.22 e Å⁻³
2371 reflections	Δρ_min = −0.21 e Å⁻³
199 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 Å) and 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	1.05849 (13)	0.30993 (11)	0.29083 (7)	0.0271 (2)
O2	0.92419 (13)	0.42696 (12)	0.14651 (7)	0.0299 (2)
O3	0.43044 (13)	0.53972 (11)	0.33020 (7)	0.0292 (2)
N1	0.52900 (16)	0.50161 (13)	0.14932 (9)	0.0256 (3)
N2	0.35679 (16)	0.56386 (13)	0.09797 (9)	0.0245 (3)
C1	0.73626 (18)	0.41687 (14)	0.31115 (10)	0.0220 (3)
C2	0.74197 (18)	0.37498 (14)	0.42062 (10)	0.0233 (3)
H2	0.6338	0.3978	0.4656	0.028*
C3	0.90772 (18)	0.29704 (14)	0.46963 (10)	0.0240 (3)
C4	0.9195 (2)	0.24825 (16)	0.58159 (11)	0.0275 (3)
H4	0.8142	0.2670	0.6296	0.033*
C5	1.0850 (2)	0.17297 (16)	0.62133 (11)	0.0300 (3)
H5	1.0926	0.1391	0.6967	0.036*
C6	1.2410 (2)	0.14627 (16)	0.55202 (11)	0.0305 (3)
H6	1.3550	0.0960	0.5812	0.037*
C7	1.2321 (2)	0.19208 (16)	0.44109 (11)	0.0295 (3)
H7	1.3377	0.1730	0.3934	0.035*
C8	1.06438 (19)	0.26654 (15)	0.40167 (10)	0.0243 (3)
C9	0.90475 (18)	0.38814 (15)	0.24263 (10)	0.0236 (3)
C10	0.55367 (18)	0.49380 (14)	0.26524 (10)	0.0229 (3)
C11	0.35631 (19)	0.73381 (15)	0.11707 (9)	0.0246 (3)
C12	0.5353 (2)	0.83552 (17)	0.13527 (11)	0.0324 (3)
H12	0.6626	0.7916	0.1390	0.039*
C13	0.5280 (2)	1.00138 (18)	0.14802 (13)	0.0401 (4)
H13	0.6509	1.0703	0.1608	0.048*
C14	0.3449 (2)	1.06733 (18)	0.14238 (12)	0.0390 (4)
H14	0.3410	1.1810	0.1518	0.047*
C15	0.1668 (2)	0.96594 (18)	0.12283 (12)	0.0367 (3)
H15	0.0400	1.0106	0.1185	0.044*
C16	0.1711 (2)	0.80054 (16)	0.10956 (11)	0.0300 (3)
H16	0.0478	0.7323	0.0953	0.036*
H2N	0.242 (3)	0.5112 (19)	0.1179 (14)	0.033 (4)*
H1N	0.621 (3)	0.472 (2)	0.1014 (16)	0.043 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0260 (5)	0.0348 (5)	0.0226 (4)	0.0082 (4)	0.0054 (3)	0.0060 (4)
O2	0.0274 (5)	0.0422 (6)	0.0222 (4)	0.0063 (4)	0.0070 (3)	0.0075 (4)
O3	0.0284 (5)	0.0393 (5)	0.0221 (4)	0.0101 (4)	0.0069 (4)	0.0040 (4)
N1	0.0259 (5)	0.0337 (6)	0.0194 (5)	0.0111 (4)	0.0041 (4)	0.0048 (4)
N2	0.0230 (5)	0.0297 (6)	0.0218 (5)	0.0067 (4)	0.0027 (4)	0.0048 (4)
C1	0.0234 (6)	0.0217 (6)	0.0207 (6)	0.0020 (4)	0.0035 (5)	0.0012 (4)
C2	0.0247 (6)	0.0240 (6)	0.0210 (6)	0.0021 (4)	0.0037 (5)	0.0012 (4)
C3	0.0264 (6)	0.0227 (6)	0.0222 (6)	0.0016 (5)	0.0014 (5)	0.0014 (5)
C4	0.0308 (7)	0.0289 (7)	0.0232 (6)	0.0030 (5)	0.0036 (5)	0.0043 (5)
C5	0.0358 (7)	0.0296 (7)	0.0243 (6)	0.0027 (5)	−0.0012 (5)	0.0065 (5)
C6	0.0301 (7)	0.0295 (7)	0.0317 (7)	0.0061 (5)	−0.0029 (5)	0.0056 (5)
C7	0.0274 (7)	0.0318 (7)	0.0299 (6)	0.0068 (5)	0.0031 (5)	0.0030 (5)
C8	0.0274 (6)	0.0240 (6)	0.0211 (6)	0.0015 (5)	0.0011 (5)	0.0029 (4)
C9	0.0244 (6)	0.0246 (6)	0.0215 (6)	0.0022 (4)	0.0020 (5)	0.0020 (4)
C10	0.0250 (6)	0.0239 (6)	0.0200 (6)	0.0026 (4)	0.0043 (5)	0.0022 (4)
C11	0.0297 (6)	0.0299 (7)	0.0156 (5)	0.0065 (5)	0.0048 (4)	0.0038 (4)
C12	0.0299 (7)	0.0364 (8)	0.0307 (7)	0.0051 (5)	0.0025 (5)	0.0025 (5)
C13	0.0423 (8)	0.0360 (8)	0.0409 (8)	−0.0017 (6)	0.0064 (6)	0.0015 (6)
C14	0.0562 (9)	0.0290 (7)	0.0345 (7)	0.0098 (6)	0.0128 (7)	0.0044 (5)
C15	0.0423 (8)	0.0398 (8)	0.0325 (7)	0.0181 (6)	0.0097 (6)	0.0079 (6)
C16	0.0292 (7)	0.0354 (7)	0.0272 (6)	0.0086 (5)	0.0051 (5)	0.0054 (5)

Geometric parameters (Å, º) top

O1—C9	1.3687 (14)	C5—C6	1.3921 (19)
O1—C8	1.3774 (14)	C5—H5	0.9500
O2—C9	1.2158 (15)	C6—C7	1.3854 (18)
O3—C10	1.2245 (15)	C6—H6	0.9500
N1—C10	1.3528 (15)	C7—C8	1.3874 (18)
N1—N2	1.4064 (14)	C7—H7	0.9500
N1—H1N	0.896 (18)	C11—C12	1.3899 (19)
N2—C11	1.4184 (16)	C11—C16	1.3939 (17)
N2—H2N	0.911 (17)	C12—C13	1.388 (2)
C1—C2	1.3573 (16)	C12—H12	0.9500
C1—C9	1.4581 (17)	C13—C14	1.378 (2)
C1—C10	1.5027 (16)	C13—H13	0.9500
C2—C3	1.4315 (17)	C14—C15	1.384 (2)
C2—H2	0.9500	C14—H14	0.9500
C3—C8	1.3915 (18)	C15—C16	1.382 (2)
C3—C4	1.4064 (17)	C15—H15	0.9500
C4—C5	1.3809 (18)	C16—H16	0.9500
C4—H4	0.9500

C9—O1—C8	122.88 (10)	O1—C8—C7	116.96 (11)
C10—N1—N2	120.49 (10)	O1—C8—C3	120.67 (11)
C10—N1—H1N	123.5 (11)	C7—C8—C3	122.37 (11)
N2—N1—H1N	116.0 (11)	O2—C9—O1	115.97 (10)
N1—N2—C11	115.52 (10)	O2—C9—C1	126.82 (11)
N1—N2—H2N	109.7 (10)	O1—C9—C1	117.20 (10)
C11—N2—H2N	112.6 (10)	O3—C10—N1	122.64 (11)
C2—C1—C9	119.98 (11)	O3—C10—C1	120.63 (11)
C2—C1—C10	117.83 (11)	N1—C10—C1	116.64 (10)
C9—C1—C10	122.18 (10)	C12—C11—C16	119.18 (12)
C1—C2—C3	121.33 (11)	C12—C11—N2	121.77 (11)
C1—C2—H2	119.3	C16—C11—N2	118.90 (12)
C3—C2—H2	119.3	C13—C12—C11	119.95 (13)
C8—C3—C4	118.47 (11)	C13—C12—H12	120.0
C8—C3—C2	117.82 (11)	C11—C12—H12	120.0
C4—C3—C2	123.71 (11)	C14—C13—C12	120.85 (14)
C5—C4—C3	119.62 (12)	C14—C13—H13	119.6
C5—C4—H4	120.2	C12—C13—H13	119.6
C3—C4—H4	120.2	C13—C14—C15	119.14 (13)
C4—C5—C6	120.62 (12)	C13—C14—H14	120.4
C4—C5—H5	119.7	C15—C14—H14	120.4
C6—C5—H5	119.7	C16—C15—C14	120.81 (13)
C7—C6—C5	120.82 (12)	C16—C15—H15	119.6
C7—C6—H6	119.6	C14—C15—H15	119.6
C5—C6—H6	119.6	C15—C16—C11	120.04 (13)
C6—C7—C8	118.10 (12)	C15—C16—H16	120.0
C6—C7—H7	121.0	C11—C16—H16	120.0
C8—C7—H7	121.0

C10—N1—N2—C11	74.99 (14)	C2—C1—C9—O2	−175.93 (12)
C9—C1—C2—C3	−2.32 (18)	C10—C1—C9—O2	3.5 (2)
C10—C1—C2—C3	178.22 (10)	C2—C1—C9—O1	3.79 (17)
C1—C2—C3—C8	0.51 (18)	C10—C1—C9—O1	−176.78 (10)
C1—C2—C3—C4	−178.72 (11)	N2—N1—C10—O3	−0.14 (19)
C8—C3—C4—C5	0.41 (19)	N2—N1—C10—C1	176.63 (10)
C2—C3—C4—C5	179.64 (12)	C2—C1—C10—O3	11.13 (18)
C3—C4—C5—C6	0.6 (2)	C9—C1—C10—O3	−168.32 (11)
C4—C5—C6—C7	−1.1 (2)	C2—C1—C10—N1	−165.71 (11)
C5—C6—C7—C8	0.6 (2)	C9—C1—C10—N1	14.85 (17)
C9—O1—C8—C7	−178.13 (11)	N1—N2—C11—C12	28.34 (15)
C9—O1—C8—C3	1.88 (18)	N1—N2—C11—C16	−156.03 (11)
C6—C7—C8—O1	−179.58 (11)	C16—C11—C12—C13	1.27 (19)
C6—C7—C8—C3	0.4 (2)	N2—C11—C12—C13	176.89 (11)
C4—C3—C8—O1	179.08 (11)	C11—C12—C13—C14	−0.3 (2)
C2—C3—C8—O1	−0.19 (18)	C12—C13—C14—C15	−0.5 (2)
C4—C3—C8—C7	−0.91 (19)	C13—C14—C15—C16	0.3 (2)
C2—C3—C8—C7	179.82 (11)	C14—C15—C16—C11	0.7 (2)
C8—O1—C9—O2	176.16 (10)	C12—C11—C16—C15	−1.48 (18)
C8—O1—C9—C1	−3.59 (17)	N2—C11—C16—C15	−177.22 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2ⁱ	0.896 (18)	2.327 (18)	3.0498 (14)	137.7 (15)
N1—H1N···O2	0.896 (18)	2.112 (18)	2.7544 (13)	127.8 (15)
N2—H2N···O2ⁱⁱ	0.911 (17)	2.243 (17)	3.1358 (14)	166.3 (14)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2ⁱ	0.896 (18)	2.327 (18)	3.0498 (14)	137.7 (15)
N1—H1N···O2	0.896 (18)	2.112 (18)	2.7544 (13)	127.8 (15)
N2—H2N···O2ⁱⁱ	0.911 (17)	2.243 (17)	3.1358 (14)	166.3 (14)

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

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