2-Azido-1-(3,6-dichloro-9H-fluoren-1-yl)ethanone.

In the title compound, C(15)H(9)Cl(2)N(3)O, an intra-molecular C-H⋯O inter-action generates an S(7) ring motif. The cyclo-penta-1,3-diene ring forms dihedral angles of 1.93 (6) and 2.78 (6)° with its attached benzene rings. In the crystal, mol-ecules are linked by C-H⋯N and C-H⋯O hydrogen bonds, thereby forming layers lying parallel to the ac plane. The crystal also features a π-π inter-action with a centroid-centroid distance of 3.5612 (6) Å.

Related literature

For the mutagenic activity of azides, see: Sander & Muehlbour (1977 ▶); Nilan et al. (1973 ▶); Owais et al. (1983 ▶). For the preparation of 1,2,3-triazoles via 1,3-dipolar cyclo­addition reactions of azides with substituted acetyl­ene compounds, see: Purvisis et al. (1984 ▶); Patei & Smalley (1984 ▶). For a related fused-ring structure, see: Molins et al. (2002 ▶). For related azide structures, see: Basanagouda et al. (2010 ▶); Karthikeyan et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H9Cl2N3O

M = 318.15

Monoclinic,

a = 10.7303 (1) Å

b = 18.7012 (3) Å

c = 6.8952 (1) Å

β = 98.61°

V = 1368.06 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 100 K

0.35 × 0.21 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.850, T max = 0.936

15671 measured reflections

4003 independent reflections

3599 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.085

S = 1.03

4003 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036762/hb6387sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036762/hb6387Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036762/hb6387Isup3.cml

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

C15H9Cl2N3O	F(000) = 648
Mr = 318.15	Dx = 1.545 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7886 reflections
a = 10.7303 (1) Å	θ = 2.2–30.0°
b = 18.7012 (3) Å	µ = 0.48 mm−1
c = 6.8952 (1) Å	T = 100 K
β = 98.61°	Block, yellow
V = 1368.06 (3) Å3	0.35 × 0.21 × 0.14 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4003 independent reflections
Radiation source: fine-focus sealed tube	3599 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 30.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.850, Tmax = 0.936	k = −26→24
15671 measured reflections	l = −9→9

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0436P)2 + 0.561P] where P = (Fo2 + 2Fc2)/3
4003 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.86335 (3)	0.015258 (16)	0.78440 (5)	0.02477 (8)
Cl2	0.69062 (3)	0.556390 (16)	0.75596 (5)	0.02593 (9)
O1	0.41319 (8)	0.27518 (5)	0.49870 (12)	0.02012 (18)
N1	0.19994 (10)	0.32713 (6)	0.62768 (18)	0.0257 (2)
N2	0.18912 (9)	0.26184 (6)	0.63263 (15)	0.0216 (2)
N3	0.16346 (11)	0.20274 (7)	0.6281 (2)	0.0321 (3)
C1	0.82735 (10)	0.22727 (6)	0.76076 (15)	0.0156 (2)
C2	0.88066 (10)	0.15948 (6)	0.78230 (16)	0.0174 (2)
H2A	0.9693	0.1533	0.8121	0.021*
C3	0.79995 (11)	0.10118 (6)	0.75884 (16)	0.0176 (2)
C4	0.66945 (11)	0.10914 (6)	0.71603 (16)	0.0175 (2)
H4A	0.6166	0.0681	0.7016	0.021*
C5	0.61693 (10)	0.17715 (6)	0.69457 (16)	0.0159 (2)
H5A	0.5281	0.1829	0.6654	0.019*
C6	0.69576 (10)	0.23714 (6)	0.71629 (15)	0.0143 (2)
C7	0.67029 (10)	0.31487 (6)	0.70872 (15)	0.0143 (2)
C8	0.55863 (10)	0.35588 (6)	0.67711 (15)	0.0155 (2)
C9	0.56735 (11)	0.43036 (6)	0.69421 (16)	0.0181 (2)
H9A	0.4927	0.4584	0.6765	0.022*
C10	0.68399 (11)	0.46365 (7)	0.73686 (16)	0.0185 (2)
C11	0.79532 (11)	0.42465 (7)	0.76498 (16)	0.0182 (2)
H11A	0.8748	0.4478	0.7923	0.022*
C12	0.78680 (10)	0.35082 (6)	0.75198 (15)	0.0156 (2)
C13	0.89409 (10)	0.29828 (6)	0.78215 (16)	0.0165 (2)
H13A	0.9442	0.3035	0.9141	0.020*
H13B	0.9502	0.3043	0.6817	0.020*
C14	0.43135 (10)	0.32382 (6)	0.61632 (16)	0.0164 (2)
C15	0.32381 (11)	0.35493 (7)	0.71116 (18)	0.0207 (2)
H15A	0.3391	0.3442	0.8533	0.025*
H15B	0.3236	0.4076	0.6958	0.025*

	U11	U22	U33	U12	U13	U23
Cl1	0.02445 (15)	0.01773 (15)	0.03227 (16)	0.00395 (10)	0.00465 (11)	0.00274 (11)
Cl2	0.03214 (17)	0.01536 (15)	0.02921 (16)	−0.00146 (11)	0.00100 (12)	−0.00078 (11)
O1	0.0170 (4)	0.0224 (4)	0.0204 (4)	−0.0007 (3)	0.0008 (3)	−0.0015 (3)
N1	0.0152 (5)	0.0260 (6)	0.0360 (6)	0.0035 (4)	0.0041 (4)	0.0048 (5)
N2	0.0107 (4)	0.0299 (6)	0.0239 (5)	0.0001 (4)	0.0015 (3)	0.0012 (4)
N3	0.0203 (5)	0.0298 (7)	0.0446 (7)	−0.0036 (5)	−0.0006 (5)	0.0043 (5)
C1	0.0152 (5)	0.0198 (6)	0.0119 (5)	−0.0006 (4)	0.0026 (4)	0.0003 (4)
C2	0.0157 (5)	0.0205 (6)	0.0161 (5)	0.0016 (4)	0.0028 (4)	0.0005 (4)
C3	0.0205 (5)	0.0169 (5)	0.0158 (5)	0.0023 (4)	0.0041 (4)	0.0014 (4)
C4	0.0189 (5)	0.0174 (6)	0.0164 (5)	−0.0016 (4)	0.0035 (4)	0.0001 (4)
C5	0.0148 (5)	0.0185 (5)	0.0145 (5)	−0.0009 (4)	0.0023 (4)	0.0006 (4)
C6	0.0152 (5)	0.0175 (5)	0.0106 (4)	0.0007 (4)	0.0029 (3)	0.0005 (4)
C7	0.0150 (5)	0.0173 (5)	0.0111 (4)	−0.0007 (4)	0.0031 (3)	−0.0001 (4)
C8	0.0155 (5)	0.0187 (5)	0.0125 (4)	0.0003 (4)	0.0026 (3)	0.0001 (4)
C9	0.0202 (5)	0.0187 (6)	0.0154 (5)	0.0017 (4)	0.0027 (4)	0.0006 (4)
C10	0.0244 (6)	0.0150 (5)	0.0159 (5)	−0.0012 (4)	0.0028 (4)	−0.0006 (4)
C11	0.0195 (5)	0.0192 (6)	0.0156 (5)	−0.0030 (4)	0.0019 (4)	−0.0003 (4)
C12	0.0159 (5)	0.0187 (5)	0.0123 (4)	−0.0013 (4)	0.0027 (4)	0.0000 (4)
C13	0.0140 (4)	0.0192 (5)	0.0163 (5)	−0.0010 (4)	0.0021 (4)	−0.0007 (4)
C14	0.0150 (5)	0.0176 (5)	0.0164 (5)	0.0019 (4)	0.0018 (4)	0.0040 (4)
C15	0.0165 (5)	0.0212 (6)	0.0252 (6)	0.0022 (4)	0.0056 (4)	0.0007 (4)

Cl1—C3	1.7436 (12)	C6—C7	1.4787 (16)
Cl2—C10	1.7400 (13)	C7—C12	1.4115 (15)
O1—C14	1.2147 (15)	C7—C8	1.4117 (15)
N1—N2	1.2275 (16)	C8—C9	1.3997 (17)
N1—C15	1.4627 (16)	C8—C14	1.4930 (15)
N2—N3	1.1382 (17)	C9—C10	1.3895 (16)
C1—C2	1.3896 (16)	C9—H9A	0.9500
C1—C6	1.4114 (15)	C10—C11	1.3882 (17)
C1—C13	1.5055 (16)	C11—C12	1.3856 (17)
C2—C3	1.3867 (17)	C11—H11A	0.9500
C2—H2A	0.9500	C12—C13	1.5042 (16)
C3—C4	1.3951 (16)	C13—H13A	0.9900
C4—C5	1.3901 (16)	C13—H13B	0.9900
C4—H4A	0.9500	C14—C15	1.5244 (16)
C5—C6	1.3995 (16)	C15—H15A	0.9900
C5—H5A	0.9500	C15—H15B	0.9900
N2—N1—C15	115.27 (10)	C10—C9—H9A	119.7
N3—N2—N1	171.32 (12)	C8—C9—H9A	119.7
C2—C1—C6	121.67 (11)	C11—C10—C9	121.55 (11)
C2—C1—C13	127.74 (10)	C11—C10—Cl2	119.25 (9)
C6—C1—C13	110.59 (10)	C9—C10—Cl2	119.21 (9)
C3—C2—C1	117.70 (10)	C12—C11—C10	117.86 (11)
C3—C2—H2A	121.2	C12—C11—H11A	121.1
C1—C2—H2A	121.2	C10—C11—H11A	121.1
C2—C3—C4	122.04 (11)	C11—C12—C7	122.41 (10)
C2—C3—Cl1	119.03 (9)	C11—C12—C13	126.89 (10)
C4—C3—Cl1	118.93 (9)	C7—C12—C13	110.70 (10)
C5—C4—C3	119.88 (11)	C12—C13—C1	102.69 (9)
C5—C4—H4A	120.1	C12—C13—H13A	111.2
C3—C4—H4A	120.1	C1—C13—H13A	111.2
C4—C5—C6	119.55 (10)	C12—C13—H13B	111.2
C4—C5—H5A	120.2	C1—C13—H13B	111.2
C6—C5—H5A	120.2	H13A—C13—H13B	109.1
C5—C6—C1	119.17 (11)	O1—C14—C8	122.46 (10)
C5—C6—C7	132.74 (10)	O1—C14—C15	121.08 (10)
C1—C6—C7	108.05 (10)	C8—C14—C15	116.46 (10)
C12—C7—C8	118.58 (11)	N1—C15—C14	113.40 (10)
C12—C7—C6	107.91 (9)	N1—C15—H15A	108.9
C8—C7—C6	133.44 (10)	C14—C15—H15A	108.9
C9—C8—C7	118.89 (10)	N1—C15—H15B	108.9
C9—C8—C14	118.04 (10)	C14—C15—H15B	108.9
C7—C8—C14	123.01 (10)	H15A—C15—H15B	107.7
C10—C9—C8	120.69 (11)
C6—C1—C2—C3	−0.08 (16)	C14—C8—C9—C10	−175.49 (10)
C13—C1—C2—C3	178.91 (10)	C8—C9—C10—C11	−0.36 (17)
C1—C2—C3—C4	−0.31 (16)	C8—C9—C10—Cl2	179.77 (8)
C1—C2—C3—Cl1	179.91 (8)	C9—C10—C11—C12	−0.91 (16)
C2—C3—C4—C5	0.37 (17)	Cl2—C10—C11—C12	178.96 (8)
Cl1—C3—C4—C5	−179.85 (8)	C10—C11—C12—C7	0.99 (16)
C3—C4—C5—C6	−0.03 (16)	C10—C11—C12—C13	−178.30 (10)
C4—C5—C6—C1	−0.35 (15)	C8—C7—C12—C11	0.19 (16)
C4—C5—C6—C7	−177.92 (10)	C6—C7—C12—C11	−177.22 (10)
C2—C1—C6—C5	0.41 (16)	C8—C7—C12—C13	179.58 (9)
C13—C1—C6—C5	−178.74 (9)	C6—C7—C12—C13	2.18 (12)
C2—C1—C6—C7	178.53 (10)	C11—C12—C13—C1	176.92 (10)
C13—C1—C6—C7	−0.62 (12)	C7—C12—C13—C1	−2.44 (11)
C5—C6—C7—C12	176.80 (11)	C2—C1—C13—C12	−177.27 (10)
C1—C6—C7—C12	−0.96 (11)	C6—C1—C13—C12	1.82 (11)
C5—C6—C7—C8	−0.1 (2)	C9—C8—C14—O1	137.71 (12)
C1—C6—C7—C8	−177.82 (11)	C7—C8—C14—O1	−39.20 (16)
C12—C7—C8—C9	−1.45 (15)	C9—C8—C14—C15	−42.76 (14)
C6—C7—C8—C9	175.15 (11)	C7—C8—C14—C15	140.33 (11)
C12—C7—C8—C14	175.44 (10)	N2—N1—C15—C14	56.63 (15)
C6—C7—C8—C14	−7.96 (18)	O1—C14—C15—N1	−7.46 (16)
C7—C8—C9—C10	1.55 (16)	C8—C14—C15—N1	173.01 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1	0.95	2.32	3.0134 (14)	129
C13—H13A···N3i	0.99	2.59	3.4613 (16)	147
C15—H15A···O1ii	0.99	2.53	3.1941 (15)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1	0.95	2.32	3.0134 (14)	129
C13—H13A⋯N3i	0.99	2.59	3.4613 (16)	147
C15—H15A⋯O1ii	0.99	2.53	3.1941 (15)	125

Symmetry codes: (i) ; (ii) .