4-Azido-methyl-7-methyl-2-oxo-2H-chromene-6-sulfonyl azide.

In the title compound, C(11)H(8)N(6)O(4)S, the plane of the coumarin aromatic ring is twisted by 17.2 (2)° with respect to the plane of the azide group bound to the methyl-ene substituent, whereas it is twisted by 83.2 (2)° to the plane of the azide attached to the sulfonyl group. The crystal structure is stabilized by weak C-H⋯O inter-actions, leading to the formation of dimers with R(2) (2)(12) graph-set motifs. These dimers are further linked by weak S-O⋯π and π-π contacts [centroid-centroid distance = 3.765 (2) Å], leading to the formation of a layered structure.

Related literature

For azides, see: Scriven & Turnbull (1988 ▶); Amblard et al. (2009 ▶). For 4-azido­methyl­coumarin derivatives, see: Melavanki et al. (2008 ▶, 2009 ▶, 2010 ▶); Naik & Kullkarni (2010 ▶); Basanagouda et al. (2010 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H8N6O4S

M = 320.29

Orthorhombic,

a = 13.5452 (12) Å

b = 27.952 (3) Å

c = 14.1107 (13) Å

V = 5342.5 (9) Å3

Z = 16

Mo Kα radiation

μ = 0.27 mm−1

T = 292 K

0.24 × 0.16 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.891, T max = 0.973

11344 measured reflections

3124 independent reflections

2677 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.102

S = 1.05

3124 reflections

201 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1438 Friedel pairs

Flack parameter: 0.09 (8)

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039693/dn2607sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039693/dn2607Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H8N6O4S	Dx = 1.593 Mg m−3
Mr = 320.29	Melting point: 406 K
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 400 reflections
a = 13.5452 (12) Å	θ = 1.0–28.0°
b = 27.952 (3) Å	µ = 0.27 mm−1
c = 14.1107 (13) Å	T = 292 K
V = 5342.5 (9) Å3	Hexagonal, pale yellow
Z = 16	0.24 × 0.16 × 0.10 mm
F(000) = 2624

Bruker SMART APEX CCD diffractometer	3124 independent reflections
Radiation source: fine-focus sealed tube	2677 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −17→0
Tmin = 0.891, Tmax = 0.973	k = −36→0
11344 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0532P)2 + 3.5426P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3124 reflections	Δρmax = 0.26 e Å−3
201 parameters	Δρmin = −0.21 e Å−3
7 restraints	Absolute structure: Flack (1983), 1438 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.09 (8)

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.

	x	y	z	Uiso*/Ueq
S1	0.85568 (4)	0.83758 (2)	0.50177 (5)	0.04317 (17)
O1	0.47627 (11)	0.93758 (5)	0.47959 (14)	0.0462 (4)
O2	0.31442 (12)	0.93929 (6)	0.49151 (18)	0.0610 (6)
O3	0.83522 (13)	0.78772 (6)	0.5081 (2)	0.0663 (6)
O4	0.92870 (14)	0.85453 (7)	0.43818 (16)	0.0598 (5)
N1	0.89734 (14)	0.85727 (8)	0.60674 (18)	0.0507 (5)
N2	0.86115 (15)	0.83563 (8)	0.67677 (19)	0.0511 (6)
N3	0.8356 (2)	0.81892 (11)	0.7443 (3)	0.0727 (8)
N4	0.37159 (16)	0.76434 (8)	0.4783 (2)	0.0643 (8)
N5	0.36677 (14)	0.72360 (8)	0.4993 (2)	0.0494 (5)
N6	0.35192 (18)	0.68477 (9)	0.5172 (3)	0.0715 (8)
C2	0.38675 (17)	0.91435 (8)	0.4834 (2)	0.0439 (6)
C3	0.38818 (17)	0.86301 (8)	0.4776 (2)	0.0436 (6)
H3	0.3284	0.8467	0.4752	0.052*
C4	0.47186 (17)	0.83767 (7)	0.47560 (17)	0.0370 (5)
C5	0.65857 (15)	0.84097 (8)	0.48129 (17)	0.0372 (5)
H5	0.6634	0.8078	0.4815	0.045*
C6	0.74334 (15)	0.86865 (8)	0.48503 (18)	0.0368 (5)
C7	0.74063 (16)	0.91904 (8)	0.48102 (17)	0.0366 (5)
C8	0.64872 (16)	0.94005 (8)	0.47701 (18)	0.0397 (6)
H8	0.6439	0.9732	0.4741	0.048*
C9	0.56344 (16)	0.91278 (8)	0.47726 (18)	0.0371 (5)
C10	0.56574 (15)	0.86284 (7)	0.47717 (17)	0.0354 (5)
C11	0.83110 (18)	0.95033 (9)	0.4850 (2)	0.0507 (7)
H11A	0.8697	0.9457	0.4287	0.076*
H11B	0.8698	0.9420	0.5395	0.076*
H11C	0.8114	0.9833	0.4893	0.076*
C12	0.47394 (17)	0.78398 (8)	0.4712 (2)	0.0482 (7)
H12A	0.5036	0.7738	0.4119	0.058*
H12B	0.5138	0.7716	0.5227	0.058*

	U11	U22	U33	U12	U13	U23
S1	0.0256 (2)	0.0409 (3)	0.0630 (4)	0.0027 (2)	−0.0001 (3)	−0.0076 (3)
O1	0.0301 (7)	0.0290 (7)	0.0796 (13)	0.0036 (6)	−0.0053 (9)	0.0013 (8)
O2	0.0330 (8)	0.0437 (9)	0.1064 (17)	0.0092 (7)	−0.0043 (12)	−0.0052 (11)
O3	0.0391 (9)	0.0387 (9)	0.1212 (18)	0.0081 (7)	−0.0105 (13)	−0.0100 (12)
O4	0.0346 (9)	0.0800 (14)	0.0647 (12)	0.0016 (9)	0.0090 (9)	−0.0099 (11)
N1	0.0365 (11)	0.0561 (13)	0.0595 (14)	−0.0065 (9)	−0.0045 (10)	0.0077 (11)
N2	0.0321 (11)	0.0519 (14)	0.0693 (16)	0.0087 (10)	−0.0030 (11)	0.0056 (12)
N3	0.0538 (14)	0.0844 (19)	0.080 (2)	0.0118 (13)	0.0103 (15)	0.0282 (17)
N4	0.0326 (10)	0.0369 (11)	0.123 (3)	−0.0022 (8)	−0.0061 (13)	0.0063 (13)
N5	0.0336 (9)	0.0501 (13)	0.0645 (14)	−0.0067 (8)	−0.0001 (11)	−0.0062 (13)
N6	0.0595 (15)	0.0435 (13)	0.111 (3)	−0.0128 (11)	0.0026 (15)	0.0127 (15)
C2	0.0319 (11)	0.0366 (12)	0.0631 (17)	0.0037 (8)	−0.0045 (11)	−0.0015 (12)
C3	0.0293 (10)	0.0351 (11)	0.0662 (17)	−0.0035 (8)	−0.0032 (11)	0.0006 (11)
C4	0.0292 (10)	0.0308 (10)	0.0511 (14)	−0.0019 (8)	−0.0037 (10)	−0.0017 (11)
C5	0.0299 (10)	0.0315 (10)	0.0502 (15)	0.0013 (8)	−0.0011 (10)	−0.0032 (10)
C6	0.0271 (9)	0.0356 (10)	0.0476 (13)	0.0018 (8)	−0.0006 (10)	−0.0048 (10)
C7	0.0346 (11)	0.0318 (10)	0.0433 (14)	−0.0053 (8)	0.0007 (10)	−0.0012 (10)
C8	0.0382 (11)	0.0271 (10)	0.0540 (15)	−0.0019 (8)	−0.0027 (12)	0.0018 (10)
C9	0.0293 (11)	0.0326 (11)	0.0495 (13)	0.0025 (8)	−0.0036 (10)	0.0000 (10)
C10	0.0284 (10)	0.0306 (10)	0.0473 (13)	−0.0019 (8)	−0.0023 (10)	−0.0003 (9)
C11	0.0356 (11)	0.0391 (12)	0.077 (2)	−0.0089 (9)	0.0015 (14)	−0.0030 (14)
C12	0.0310 (11)	0.0321 (10)	0.0814 (19)	−0.0031 (9)	−0.0035 (12)	−0.0037 (12)

S1—O4	1.417 (2)	C4—C12	1.502 (3)
S1—O3	1.4237 (18)	C5—C6	1.386 (3)
S1—N1	1.678 (3)	C5—C10	1.399 (3)
S1—C6	1.768 (2)	C5—H5	0.9300
O1—C9	1.370 (3)	C6—C7	1.410 (3)
O1—C2	1.376 (3)	C7—C8	1.378 (3)
O2—C2	1.208 (3)	C7—C11	1.507 (3)
N1—N2	1.258 (3)	C8—C9	1.384 (3)
N2—N3	1.116 (4)	C8—H8	0.9300
N4—N5	1.178 (3)	C9—C10	1.396 (3)
N4—C12	1.495 (3)	C11—H11A	0.9600
N5—N6	1.133 (3)	C11—H11B	0.9600
C2—C3	1.438 (3)	C11—H11C	0.9600
C3—C4	1.337 (3)	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C10	1.453 (3)
O4—S1—O3	120.17 (13)	C7—C6—S1	121.23 (16)
O4—S1—N1	102.39 (12)	C8—C7—C6	116.80 (19)
O3—S1—N1	109.36 (14)	C8—C7—C11	119.3 (2)
O4—S1—C6	110.61 (12)	C6—C7—C11	123.9 (2)
O3—S1—C6	108.77 (11)	C7—C8—C9	121.3 (2)
N1—S1—C6	104.26 (11)	C7—C8—H8	119.4
C9—O1—C2	121.45 (17)	C9—C8—H8	119.4
N2—N1—S1	113.88 (19)	O1—C9—C8	116.16 (18)
N3—N2—N1	173.0 (3)	O1—C9—C10	121.68 (19)
N5—N4—C12	115.0 (2)	C8—C9—C10	122.1 (2)
N6—N5—N4	172.8 (3)	C9—C10—C5	117.18 (19)
O2—C2—O1	116.5 (2)	C9—C10—C4	117.67 (19)
O2—C2—C3	126.3 (2)	C5—C10—C4	125.13 (19)
O1—C2—C3	117.18 (19)	C7—C11—H11A	109.5
C4—C3—C2	122.8 (2)	C7—C11—H11B	109.5
C4—C3—H3	118.6	H11A—C11—H11B	109.5
C2—C3—H3	118.6	C7—C11—H11C	109.5
C3—C4—C10	119.02 (19)	H11A—C11—H11C	109.5
C3—C4—C12	123.1 (2)	H11B—C11—H11C	109.5
C10—C4—C12	117.89 (19)	N4—C12—C4	110.29 (18)
C6—C5—C10	120.1 (2)	N4—C12—H12A	109.6
C6—C5—H5	119.9	C4—C12—H12A	109.6
C10—C5—H5	119.9	N4—C12—H12B	109.6
C5—C6—C7	122.3 (2)	C4—C12—H12B	109.6
C5—C6—S1	116.36 (17)	H12A—C12—H12B	108.1
O4—S1—N1—N2	−160.77 (19)	S1—C6—C7—C11	3.5 (4)
O3—S1—N1—N2	−32.3 (2)	C6—C7—C8—C9	0.2 (4)
C6—S1—N1—N2	83.9 (2)	C11—C7—C8—C9	−177.3 (2)
C9—O1—C2—O2	175.3 (2)	C2—O1—C9—C8	−177.7 (2)
C9—O1—C2—C3	−4.6 (4)	C2—O1—C9—C10	1.0 (4)
O2—C2—C3—C4	−175.0 (3)	C7—C8—C9—O1	175.7 (2)
O1—C2—C3—C4	4.8 (4)	C7—C8—C9—C10	−3.0 (4)
C2—C3—C4—C10	−1.4 (4)	O1—C9—C10—C5	−175.7 (2)
C2—C3—C4—C12	179.0 (3)	C8—C9—C10—C5	2.9 (3)
C10—C5—C6—C7	−2.6 (4)	O1—C9—C10—C4	2.5 (3)
C10—C5—C6—S1	174.00 (18)	C8—C9—C10—C4	−178.8 (2)
O4—S1—C6—C5	134.2 (2)	C6—C5—C10—C9	−0.1 (3)
O3—S1—C6—C5	0.2 (3)	C6—C5—C10—C4	−178.3 (2)
N1—S1—C6—C5	−116.4 (2)	C3—C4—C10—C9	−2.3 (4)
O4—S1—C6—C7	−49.1 (2)	C12—C4—C10—C9	177.4 (2)
O3—S1—C6—C7	176.8 (2)	C3—C4—C10—C5	175.8 (2)
N1—S1—C6—C7	60.3 (2)	C12—C4—C10—C5	−4.5 (4)
C5—C6—C7—C8	2.6 (4)	N5—N4—C12—C4	−161.8 (3)
S1—C6—C7—C8	−173.89 (19)	C3—C4—C12—N4	−5.1 (4)
C5—C6—C7—C11	179.9 (3)	C10—C4—C12—N4	175.3 (2)

Cg is the centroid of the C5–C10 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2i	0.93	2.52	3.416 (3)	161
S1—O4···Cgii	1.417 (2)	2.963 (2)	3.931 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2i	0.93	2.52	3.416 (3)	161
S1—O4⋯Cgii	1.42 (1)	2.96 (1)	3.931 (2)	128

Symmetry codes: (i) ; (ii) .