Fluoren-9-one oxime.

In the title mol-ecule, C13H9NO, the fluorene system and the oxime group non-H atoms are essentially coplanar, with a maximum deviation from the fluorene mean plane of 0.079 (2) Å for the oxime O atom. A short intra-molecular C-H⋯O generates an S(6) ring. In the crystal, mol-ecules related by a twofold screw axis are connected by O-H⋯N hydrogen bonds, forming [100] chains Within these chains, mol-ecules related by a unit translation along [100] show π-π stacking inter-actions between their fluorene ring systems with an inter-planar distance of 3.347 (2) Å. The dihedral angle between the fluorene units of adjacent mol-ecules along the helix is 88.40 (2)°. There is a short C-H⋯π contact between the fluorene groups belonging to neighbouring chains.

Related literature

For the original procedure for the preparation of the title compound, see: Moore & Huntress (1927 ▶). For the use of the title compound as a starting material for the synthesis of bioactive compounds, see: Amlaiky et al. (1983 ▶); Ni et al. (2009 ▶); Rad et al. (2012 ▶).

Experimental

Crystal data

C13H9NO

M = 195.21

Orthorhombic,

a = 4.8009 (1) Å

b = 12.2309 (2) Å

c = 16.0247 (3) Å

V = 940.96 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.70 mm−1

T = 100 K

0.16 × 0.13 × 0.13 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.890, T max = 1.000

7588 measured reflections

1942 independent reflections

1865 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.075

S = 1.05

1942 reflections

140 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack parameter determined using 735 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2013 ▶)

Absolute structure parameter: 0.16 (13)

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within OLEX2 (Dolomanov et al., 2009 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814002669/gk2601sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814002669/gk2601Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814002669/gk2601Isup3.cml

CCDC reference:

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

C13H9NO	Dx = 1.378 Mg m−3
Mr = 195.21	Melting point = 471–472 K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
a = 4.8009 (1) Å	Cell parameters from 3850 reflections
b = 12.2309 (2) Å	θ = 4.5–76.1°
c = 16.0247 (3) Å	µ = 0.70 mm−1
V = 940.96 (3) Å3	T = 100 K
Z = 4	Block, colourless
F(000) = 408	0.16 × 0.13 × 0.13 mm

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	1942 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	1865 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.4127 pixels mm-1	θmax = 76.3°, θmin = 4.6°
ω scans	h = −6→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −14→15
Tmin = 0.890, Tmax = 1.000	l = −19→20
7588 measured reflections

Refinement on F2	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.029	w = 1/[σ2(Fo2) + (0.0384P)2 + 0.1723P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.075	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.13 e Å−3
1942 reflections	Δρmin = −0.18 e Å−3
140 parameters	Absolute structure: Flack parameter determined using 735 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.16 (13)
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq
C1	0.5506 (4)	0.58330 (13)	0.40422 (10)	0.0189 (4)
C10	0.8197 (4)	0.44386 (15)	0.17647 (10)	0.0251 (4)
C11	0.9543 (4)	0.53953 (15)	0.20052 (10)	0.0242 (4)
C12	0.8830 (4)	0.59306 (14)	0.27456 (10)	0.0219 (4)
C13	0.6741 (4)	0.54803 (13)	0.32367 (10)	0.0196 (3)
C2	0.3367 (4)	0.50126 (13)	0.42679 (10)	0.0194 (3)
C3	0.1613 (4)	0.49391 (13)	0.49503 (10)	0.0209 (3)
C4	−0.0178 (4)	0.40413 (13)	0.50050 (11)	0.0228 (4)
C5	−0.0177 (4)	0.32387 (14)	0.43891 (11)	0.0246 (4)
C6	0.1590 (4)	0.33133 (14)	0.37017 (11)	0.0235 (4)
C7	0.3353 (4)	0.42037 (13)	0.36414 (10)	0.0195 (3)
C8	0.5403 (4)	0.45037 (13)	0.30001 (10)	0.0198 (4)
C9	0.6112 (4)	0.39797 (14)	0.22607 (11)	0.0239 (4)
H1	0.898 (6)	0.773 (2)	0.4668 (17)	0.068 (9)*
H10	0.8703	0.4093	0.1256	0.030*
H11	1.0969	0.5689	0.1661	0.029*
H12	0.9750	0.6584	0.2908	0.026*
H3	0.1626	0.5485	0.5372	0.025*
H4	−0.1408	0.3978	0.5467	0.027*
H5	−0.1399	0.2631	0.4438	0.029*
H6	0.1583	0.2764	0.3283	0.028*
H9	0.5200	0.3325	0.2097	0.029*
N1	0.6059 (3)	0.66488 (11)	0.45230 (8)	0.0202 (3)
O1	0.8178 (3)	0.73127 (10)	0.42014 (7)	0.0233 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0217 (9)	0.0194 (8)	0.0158 (7)	0.0029 (6)	−0.0016 (6)	0.0013 (6)
C10	0.0300 (10)	0.0290 (8)	0.0164 (7)	0.0078 (8)	−0.0003 (7)	−0.0031 (7)
C11	0.0257 (9)	0.0289 (9)	0.0179 (8)	0.0060 (7)	0.0018 (7)	0.0038 (7)
C12	0.0266 (9)	0.0206 (7)	0.0186 (8)	0.0025 (7)	−0.0013 (7)	0.0015 (6)
C13	0.0228 (9)	0.0204 (7)	0.0155 (7)	0.0050 (7)	−0.0024 (7)	−0.0007 (6)
C2	0.0216 (8)	0.0185 (7)	0.0181 (8)	0.0028 (7)	−0.0048 (7)	0.0005 (6)
C3	0.0233 (8)	0.0219 (7)	0.0174 (7)	0.0043 (7)	−0.0018 (7)	0.0005 (6)
C4	0.0223 (8)	0.0248 (8)	0.0214 (8)	0.0028 (6)	0.0007 (8)	0.0042 (7)
C5	0.0259 (9)	0.0210 (8)	0.0268 (9)	−0.0024 (7)	−0.0015 (7)	0.0030 (7)
C6	0.0277 (10)	0.0200 (7)	0.0228 (8)	0.0012 (7)	−0.0040 (7)	−0.0025 (6)
C7	0.0209 (8)	0.0200 (7)	0.0177 (7)	0.0037 (6)	−0.0021 (6)	−0.0002 (6)
C8	0.0212 (9)	0.0202 (7)	0.0181 (8)	0.0034 (7)	−0.0032 (7)	−0.0001 (6)
C9	0.0287 (10)	0.0220 (8)	0.0209 (8)	0.0030 (7)	−0.0039 (7)	−0.0034 (6)
N1	0.0236 (8)	0.0184 (6)	0.0185 (7)	0.0010 (6)	−0.0008 (6)	0.0014 (5)
O1	0.0283 (6)	0.0217 (5)	0.0198 (6)	−0.0058 (5)	0.0010 (5)	−0.0023 (4)

C1—C13	1.484 (2)	C4—H4	0.9500
C1—C2	1.481 (2)	C5—C6	1.393 (2)
C10—C11	1.391 (3)	C5—H5	0.9500
C10—H10	0.9500	C6—C7	1.383 (2)
C11—C12	1.398 (2)	C6—H6	0.9500
C11—H11	0.9500	C7—C8	1.469 (2)
C12—C13	1.389 (2)	C8—C13	1.408 (2)
C12—H12	0.9500	C8—C9	1.389 (2)
C2—C7	1.410 (2)	C9—C10	1.396 (3)
C2—C3	1.383 (2)	C9—H9	0.9500
C3—C4	1.397 (2)	N1—C1	1.288 (2)
C3—H3	0.9500	O1—H1	0.98 (3)
C4—C5	1.392 (2)	O1—N1	1.4000 (19)
N1—O1—H1	107.7 (17)	C6—C7—C2	120.39 (16)
C1—N1—O1	112.25 (13)	C6—C7—C8	130.96 (16)
N1—C1—C2	121.43 (15)	C9—C8—C7	130.19 (16)
N1—C1—C13	131.53 (16)	C9—C8—C13	120.61 (16)
C2—C1—C13	107.00 (14)	C13—C8—C7	109.20 (14)
C3—C2—C1	131.26 (15)	C8—C9—H9	120.8
C3—C2—C7	120.97 (15)	C8—C9—C10	118.41 (16)
C7—C2—C1	107.75 (14)	C10—C9—H9	120.8
C2—C3—H3	120.8	C9—C10—H10	119.6
C2—C3—C4	118.38 (15)	C11—C10—C9	120.89 (16)
C4—C3—H3	120.8	C11—C10—H10	119.6
C3—C4—H4	119.7	C10—C11—H11	119.5
C5—C4—C3	120.63 (16)	C10—C11—C12	121.04 (17)
C5—C4—H4	119.7	C12—C11—H11	119.5
C4—C5—H5	119.5	C11—C12—H12	120.9
C4—C5—C6	120.97 (17)	C13—C12—C11	118.17 (17)
C6—C5—H5	119.5	C13—C12—H12	120.9
C5—C6—H6	120.7	C8—C13—C1	107.38 (15)
C7—C6—C5	118.66 (16)	C12—C13—C1	131.75 (16)
C7—C6—H6	120.7	C12—C13—C8	120.87 (15)
C2—C7—C8	108.64 (14)
O1—N1—C1—C2	178.85 (14)	C5—C6—C7—C2	0.5 (3)
O1—N1—C1—C13	1.2 (2)	C5—C6—C7—C8	−179.68 (17)
N1—C1—C2—C3	1.5 (3)	C6—C7—C8—C9	1.3 (3)
N1—C1—C2—C7	−177.14 (15)	C6—C7—C8—C13	−178.35 (18)
N1—C1—C13—C8	177.82 (17)	C7—C2—C3—C4	0.0 (2)
N1—C1—C13—C12	−1.4 (3)	C7—C8—C9—C10	−178.93 (17)
C1—C2—C3—C4	−178.52 (16)	C7—C8—C13—C1	−0.88 (18)
C1—C2—C7—C6	178.38 (15)	C7—C8—C13—C12	178.46 (15)
C1—C2—C7—C8	−1.52 (18)	C8—C9—C10—C11	0.3 (3)
C2—C1—C13—C8	−0.04 (18)	C9—C8—C13—C1	179.46 (15)
C2—C1—C13—C12	−179.28 (17)	C9—C8—C13—C12	−1.2 (2)
C2—C3—C4—C5	0.4 (2)	C9—C10—C11—C12	−0.6 (3)
C2—C7—C8—C9	−178.86 (18)	C10—C11—C12—C13	0.1 (3)
C2—C7—C8—C13	1.53 (18)	C11—C12—C13—C1	179.97 (17)
C3—C2—C7—C6	−0.5 (2)	C11—C12—C13—C8	0.8 (2)
C3—C2—C7—C8	179.64 (15)	C13—C1—C2—C3	179.66 (16)
C3—C4—C5—C6	−0.4 (3)	C13—C1—C2—C7	0.98 (18)
C4—C5—C6—C7	0.0 (3)	C13—C8—C9—C10	0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1	0.95	2.38	2.898 (2)	114
O1—H1···N1i	0.98 (3)	1.80 (3)	2.7758 (18)	169 (3)
C5—H5···Cg1ii	0.95	3.08	3.873	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1	0.95	2.38	2.898 (2)	114
O1—H1⋯N1i	0.98 (3)	1.80 (3)	2.7758 (18)	169 (3)
C5—H5⋯Cg1ii	0.95	3.08	3.873	142

Symmetry codes: (i) ; (ii) .