Crystal structure of 4-azido-methyl-6-isopropyl-2H-chromen-2-one.

In the title mol-ecule, C13H13N3O2, the benzo-pyran ring system is essentially planar, with a maximum deviation of 0.017 (1) Å. In the crystal, weak C-H⋯O hydrogen bonds link mol-ecules into ladders along [010]. In addition, π-π inter-actions between inversion-related mol-ecules, with centroid-centroid distances in the range 3.679 (2)-3.876 (2) Å, complete a two-dimensional network parallel to (001).

Related literature

For therapeutic properties of coumarin derivatives, see: Lacy & O’Kennedy (2004 ▸); Mustafa et al. (2011 ▸). For the biological activity of 2H-chromen-2-ones, see: Naik et al. (2012 ▸). For applications of organic azides, see: Kusanur et al. (2010 ▸). For structural features of coumarins, see: Moorthy et al. (2003 ▸). For related structures, see: Gowda et al. (2010 ▸); Fun et al. (2011 ▸); Nagarajaiah et al. (2013 ▸).

Experimental

Crystal data

C13H13N3O2

M = 243.26

Triclinic,

a = 6.895 (2) Å

b = 7.862 (2) Å

c = 11.592 (4) Å

α = 72.218 (6)°

β = 79.662 (5)°

γ = 82.430 (6)°

V = 586.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▸) T min = 0.983, T max = 0.985

3059 measured reflections

2026 independent reflections

1644 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.150

S = 1.07

2026 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1998 ▸); cell refinement: SAINT (Bruker, 1998 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015004387/lh5754sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015004387/lh5754Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015004387/lh5754Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015004387/lh5754fig1.tif

The mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.

Click here for additional data file.

. DOI: 10.1107/S2056989015004387/lh5754fig2.tif

Part of the crystal structure with weak hydrogen bonds shown as dashed lines. Only H atoms involved in hydrogen bonds are shown.

CCDC reference: 1051846

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

C13H13N3O2	Z = 2
Mr = 243.26	F(000) = 256
Triclinic, P1	Dx = 1.377 Mg m−3
a = 6.895 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.862 (2) Å	Cell parameters from 2028 reflections
c = 11.592 (4) Å	θ = 1.9–25.0°
α = 72.218 (6)°	µ = 0.10 mm−1
β = 79.662 (5)°	T = 100 K
γ = 82.430 (6)°	Block, colourless
V = 586.7 (3) Å3	0.18 × 0.16 × 0.16 mm

Bruker SMART APEX CCD detector diffractometer	1644 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→7
Tmin = 0.983, Tmax = 0.985	k = −9→8
3059 measured reflections	l = −13→9
2026 independent reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051	H-atom parameters constrained
wR(F2) = 0.150	w = 1/[σ2(Fo2) + (0.0929P)2 + 0.0624P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2026 reflections	Δρmax = 0.34 e Å−3
165 parameters	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.21989 (18)	0.72869 (15)	0.55787 (11)	0.0218 (4)
O2	0.25015 (19)	0.97173 (16)	0.40014 (12)	0.0275 (4)
N1	0.3566 (3)	0.5078 (2)	0.18653 (14)	0.0295 (4)
N2	0.2838 (2)	0.46732 (19)	0.11032 (14)	0.0224 (4)
N3	0.2296 (3)	0.4459 (2)	0.02953 (15)	0.0347 (5)
C1	0.3110 (3)	0.3983 (2)	0.31451 (15)	0.0208 (4)
H1A	0.4222	0.3069	0.3361	0.025*
H1B	0.1911	0.3354	0.3245	0.025*
C2	0.2481 (3)	0.8106 (2)	0.43304 (16)	0.0215 (4)
C3	0.2742 (3)	0.6957 (2)	0.35451 (16)	0.0206 (4)
H3	0.2898	0.7488	0.2683	0.025*
C4	0.2773 (2)	0.5161 (2)	0.39858 (16)	0.0185 (4)
C5	0.2560 (2)	0.2462 (2)	0.58662 (16)	0.0190 (4)
H5	0.2745	0.1667	0.5374	0.023*
C6	0.2339 (3)	0.1765 (2)	0.71344 (16)	0.0197 (4)
C7	0.2029 (3)	0.2955 (2)	0.78447 (17)	0.0223 (4)
H7	0.1848	0.2496	0.8712	0.027*
C8	0.1980 (3)	0.4781 (2)	0.73103 (16)	0.0212 (4)
H8	0.1781	0.5576	0.7803	0.025*
C9	0.2226 (2)	0.5440 (2)	0.60513 (16)	0.0190 (4)
C10	0.2516 (2)	0.4322 (2)	0.52983 (16)	0.0175 (4)
C11	0.2405 (3)	−0.0239 (2)	0.77465 (16)	0.0231 (5)
H11	0.2825	−0.0853	0.7093	0.028*
C12	0.3913 (3)	−0.0852 (2)	0.86437 (18)	0.0292 (5)
H12A	0.5230	−0.0542	0.8205	0.044*
H12B	0.3927	−0.2152	0.9012	0.044*
H12C	0.3546	−0.0253	0.9289	0.044*
C13	0.0355 (3)	−0.0808 (2)	0.83985 (18)	0.0286 (5)
H13A	−0.0161	−0.0113	0.8976	0.043*
H13B	0.0457	−0.2087	0.8844	0.043*
H13C	−0.0542	−0.0588	0.7792	0.043*

	U11	U22	U33	U12	U13	U23
O1	0.0290 (7)	0.0150 (7)	0.0213 (7)	−0.0018 (5)	−0.0036 (6)	−0.0053 (5)
O2	0.0367 (8)	0.0165 (7)	0.0283 (8)	−0.0043 (6)	−0.0056 (6)	−0.0040 (6)
N1	0.0438 (10)	0.0293 (9)	0.0185 (9)	−0.0163 (8)	−0.0034 (7)	−0.0065 (7)
N2	0.0261 (9)	0.0182 (8)	0.0198 (8)	−0.0039 (6)	−0.0012 (7)	−0.0014 (6)
N3	0.0430 (11)	0.0413 (11)	0.0214 (9)	−0.0155 (8)	−0.0077 (8)	−0.0046 (8)
C1	0.0241 (9)	0.0201 (9)	0.0164 (9)	−0.0060 (7)	−0.0017 (7)	−0.0017 (7)
C2	0.0219 (9)	0.0200 (10)	0.0217 (10)	−0.0025 (7)	−0.0040 (7)	−0.0038 (8)
C3	0.0210 (9)	0.0211 (9)	0.0187 (9)	−0.0045 (7)	−0.0032 (7)	−0.0031 (8)
C4	0.0142 (8)	0.0213 (9)	0.0200 (9)	−0.0023 (7)	−0.0033 (7)	−0.0051 (7)
C5	0.0184 (9)	0.0196 (9)	0.0200 (9)	−0.0016 (7)	−0.0027 (7)	−0.0075 (8)
C6	0.0203 (9)	0.0180 (9)	0.0205 (9)	−0.0031 (7)	−0.0032 (7)	−0.0044 (7)
C7	0.0238 (9)	0.0243 (10)	0.0181 (9)	−0.0041 (7)	−0.0030 (7)	−0.0042 (8)
C8	0.0235 (9)	0.0208 (9)	0.0218 (10)	−0.0008 (7)	−0.0026 (8)	−0.0105 (8)
C9	0.0185 (9)	0.0151 (9)	0.0227 (10)	−0.0011 (7)	−0.0037 (7)	−0.0040 (7)
C10	0.0148 (8)	0.0191 (9)	0.0192 (9)	−0.0025 (7)	−0.0028 (7)	−0.0057 (7)
C11	0.0298 (10)	0.0193 (9)	0.0189 (10)	−0.0029 (8)	−0.0013 (8)	−0.0046 (7)
C12	0.0289 (10)	0.0215 (10)	0.0317 (11)	−0.0016 (8)	−0.0049 (9)	0.0004 (8)
C13	0.0334 (11)	0.0213 (10)	0.0305 (11)	−0.0061 (8)	−0.0070 (9)	−0.0036 (8)

O1—C2	1.382 (2)	C6—C7	1.398 (3)
O1—C9	1.386 (2)	C6—C11	1.515 (2)
O2—C2	1.207 (2)	C7—C8	1.378 (2)
N1—N2	1.228 (2)	C7—H7	0.9500
N1—C1	1.471 (2)	C8—C9	1.378 (3)
N2—N3	1.133 (2)	C8—H8	0.9500
C1—C4	1.508 (2)	C9—C10	1.391 (3)
C1—H1A	0.9900	C11—C12	1.531 (3)
C1—H1B	0.9900	C11—C13	1.532 (3)
C2—C3	1.442 (3)	C11—H11	1.0000
C3—C4	1.346 (2)	C12—H12A	0.9800
C3—H3	0.9500	C12—H12B	0.9800
C4—C10	1.450 (2)	C12—H12C	0.9800
C5—C6	1.391 (2)	C13—H13A	0.9800
C5—C10	1.407 (2)	C13—H13B	0.9800
C5—H5	0.9500	C13—H13C	0.9800
C2—O1—C9	121.36 (14)	C7—C8—C9	119.10 (17)
N2—N1—C1	116.42 (14)	C7—C8—H8	120.5
N3—N2—N1	171.49 (17)	C9—C8—H8	120.5
N1—C1—C4	109.91 (14)	C8—C9—O1	115.88 (16)
N1—C1—H1A	109.7	C8—C9—C10	122.21 (16)
C4—C1—H1A	109.7	O1—C9—C10	121.90 (16)
N1—C1—H1B	109.7	C9—C10—C5	117.60 (16)
C4—C1—H1B	109.7	C9—C10—C4	117.48 (15)
H1A—C1—H1B	108.2	C5—C10—C4	124.92 (16)
O2—C2—O1	116.82 (16)	C6—C11—C12	111.82 (15)
O2—C2—C3	126.20 (17)	C6—C11—C13	111.03 (15)
O1—C2—C3	116.98 (15)	C12—C11—C13	110.35 (15)
C4—C3—C2	122.54 (17)	C6—C11—H11	107.8
C4—C3—H3	118.7	C12—C11—H11	107.8
C2—C3—H3	118.7	C13—C11—H11	107.8
C3—C4—C10	119.70 (16)	C11—C12—H12A	109.5
C3—C4—C1	121.56 (16)	C11—C12—H12B	109.5
C10—C4—C1	118.72 (15)	H12A—C12—H12B	109.5
C6—C5—C10	121.25 (16)	C11—C12—H12C	109.5
C6—C5—H5	119.4	H12A—C12—H12C	109.5
C10—C5—H5	119.4	H12B—C12—H12C	109.5
C5—C6—C7	118.58 (16)	C11—C13—H13A	109.5
C5—C6—C11	121.29 (16)	C11—C13—H13B	109.5
C7—C6—C11	120.13 (16)	H13A—C13—H13B	109.5
C8—C7—C6	121.25 (17)	C11—C13—H13C	109.5
C8—C7—H7	119.4	H13A—C13—H13C	109.5
C6—C7—H7	119.4	H13B—C13—H13C	109.5
N2—N1—C1—C4	−140.65 (17)	C2—O1—C9—C8	178.30 (14)
C9—O1—C2—O2	−177.52 (15)	C2—O1—C9—C10	−0.6 (2)
C9—O1—C2—C3	1.9 (2)	C8—C9—C10—C5	−0.2 (3)
O2—C2—C3—C4	177.40 (17)	O1—C9—C10—C5	178.68 (14)
O1—C2—C3—C4	−1.9 (3)	C8—C9—C10—C4	−179.50 (15)
C2—C3—C4—C10	0.7 (3)	O1—C9—C10—C4	−0.6 (2)
C2—C3—C4—C1	−178.12 (15)	C6—C5—C10—C9	−0.5 (3)
N1—C1—C4—C3	5.5 (2)	C6—C5—C10—C4	178.70 (15)
N1—C1—C4—C10	−173.34 (14)	C3—C4—C10—C9	0.6 (2)
C10—C5—C6—C7	1.3 (3)	C1—C4—C10—C9	179.43 (15)
C10—C5—C6—C11	−179.43 (15)	C3—C4—C10—C5	−178.67 (16)
C5—C6—C7—C8	−1.3 (3)	C1—C4—C10—C5	0.2 (2)
C11—C6—C7—C8	179.40 (15)	C5—C6—C11—C12	126.86 (18)
C6—C7—C8—C9	0.6 (3)	C7—C6—C11—C12	−53.9 (2)
C7—C8—C9—O1	−178.76 (14)	C5—C6—C11—C13	−109.42 (19)
C7—C8—C9—C10	0.2 (3)	C7—C6—C11—C13	69.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2i	0.95	2.56	3.498 (2)	168
C13—H13C···O2ii	0.98	2.55	3.524 (3)	172

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C5H5O2i	0.95	2.56	3.498(2)	168
C13H13CO2ii	0.98	2.55	3.524(3)	172

Symmetry codes: (i) ; (ii) .