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

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 intra-molecular 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 mol-ecules, forming [100] chains.

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 ▸).

Experimental

Crystal data

C16H12N2O3

M = 280.28

Triclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.107

S = 1.06

2371 reflections

199 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.21 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/S2056989015022495/ff2144sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015022495/ff2144Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015022495/ff2144Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015022495/ff2144fig1.tif

The title mol­ecule with labeling scheme and 50% probability ellipsoids. The intra­molecular N—H⋯O hydrogen bond is shown by a dotted line.

Click here for additional data file.

. DOI: 10.1107/S2056989015022495/ff2144fig2.tif

Packing viewed towards (110) with inter­molecular N—H⋯O and N—H⋯N hydrogen bonds shown, respectively, as blue and purple dotted lines.

CCDC reference: 1438684

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

C16H12N2O3	Z = 2
Mr = 280.28	F(000) = 292
Triclinic, P1	Dx = 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

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	Rint = 0.023
Detector resolution: 10.4167 pixels mm-1	θmax = 72.3°, θmin = 3.9°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −9→10
Tmin = 0.88, Tmax = 0.96	l = −14→14
4865 measured reflections

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(Fo2) + (0.0632P)2 + 0.1234P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2371 reflections	Δρmax = 0.22 e Å−3
199 parameters	Δρmin = −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)

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 Å) and included as riding contributions with isotropic displacement parameters 1.2 − 1.5 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) ; (ii) .