1,2-Di-hydro-spiro-[carbazole-3(4H),2'-[1,3]dioxolane].

In the title compound, C(14)H(15)NO(2), the hydrogenated six-membered ring of the carbazole unit adopts a half-chair conformation and the dioxolane ring points to one side of the carbazole plane. Neighbouring mol-ecules form edge-to-face inter-actions in which the NH group is directed towards an adjacent carbazole unit, with a shortest H⋯C contact of 2.72 Å. These inter-actions arrange the mol-ecules into one-dimensional herringbone-type motifs, which pack so that the methyl-ene groups of the dioxolane ring lie over the face of a neighbouring carbazole unit with a shortest H⋯C contact of 2.85 Å.

Related literature

For background literature and synthesis details, see: Ulven & Kostenis (2006 ▶); Urrutia & Rodriguez (1999 ▶).

Experimental

Crystal data

C14H15NO2

M = 229.27

Monoclinic,

a = 9.3781 (6) Å

b = 6.1467 (4) Å

c = 10.5740 (7) Å

β = 115.232 (2)°

V = 551.38 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 180 K

0.50 × 0.50 × 0.40 mm

Data collection

Bruker–Nonius X8 APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.812, T max = 0.964

7776 measured reflections

1485 independent reflections

1427 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.080

S = 1.05

1485 reflections

154 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005558/ya2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005558/ya2088Isup2.hkl

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

C14H15NO2	F(000) = 244
Mr = 229.27	Dx = 1.381 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5883 reflections
a = 9.3781 (6) Å	θ = 2.4–28.4°
b = 6.1467 (4) Å	µ = 0.09 mm−1
c = 10.5740 (7) Å	T = 180 K
β = 115.232 (2)°	Block, colourless
V = 551.38 (6) Å3	0.50 × 0.50 × 0.40 mm
Z = 2

Bruker–Nonius X8 APEXII CCD diffractometer	1485 independent reflections
Radiation source: fine-focus sealed tube	1427 reflections with I > 2σ(I)
graphite	Rint = 0.017
Thin–slice ω and φ scans	θmax = 28.4°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→12
Tmin = 0.812, Tmax = 0.964	k = −8→8
7776 measured reflections	l = −11→14

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0581P)2 + 0.0517P] where P = (Fo2 + 2Fc2)/3
1485 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.33 e Å−3
1 restraint	Δρmin = −0.16 e Å−3

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
O1	0.23032 (12)	0.56670 (18)	0.55448 (11)	0.0256 (2)
O2	0.36610 (11)	0.26085 (18)	0.56040 (10)	0.0238 (2)
N1	0.10724 (14)	−0.0286 (2)	0.12685 (12)	0.0259 (3)
H1A	0.0579	−0.1545	0.1083	0.031*
C1	0.17592 (15)	0.0682 (3)	0.04893 (14)	0.0240 (3)
C2	0.18695 (18)	−0.0023 (3)	−0.07194 (15)	0.0321 (3)
H2A	0.1415	−0.1362	−0.1153	0.038*
C3	0.2665 (2)	0.1299 (4)	−0.12652 (16)	0.0373 (4)
H3A	0.2752	0.0863	−0.2092	0.045*
C4	0.3344 (2)	0.3267 (3)	−0.06233 (18)	0.0368 (4)
H4A	0.3891	0.4134	−0.1017	0.044*
C5	0.32330 (18)	0.3972 (3)	0.05741 (15)	0.0296 (3)
H5A	0.3694	0.5312	0.1000	0.036*
C6	0.24301 (15)	0.2675 (3)	0.11475 (13)	0.0223 (3)
C7	0.21109 (15)	0.2855 (2)	0.23567 (13)	0.0206 (3)
C8	0.25187 (17)	0.4636 (2)	0.34150 (14)	0.0229 (3)
H8A	0.1820	0.5900	0.3001	0.027*
H8B	0.3620	0.5107	0.3687	0.027*
C9	0.23321 (15)	0.3857 (2)	0.47164 (14)	0.0202 (3)
C10	0.08364 (15)	0.2549 (3)	0.43550 (14)	0.0235 (3)
H10A	−0.0086	0.3484	0.3823	0.028*
H10B	0.0775	0.2110	0.5231	0.028*
C11	0.07498 (17)	0.0513 (2)	0.34942 (15)	0.0249 (3)
H11A	0.1428	−0.0641	0.4112	0.030*
H11B	−0.0347	−0.0034	0.3056	0.030*
C12	0.12847 (15)	0.1046 (2)	0.23882 (13)	0.0217 (3)
C13	0.39081 (17)	0.6225 (3)	0.63924 (16)	0.0275 (3)
H13A	0.4055	0.6671	0.7340	0.033*
H13B	0.4255	0.7426	0.5965	0.033*
C14	0.48246 (17)	0.4138 (3)	0.64530 (17)	0.0303 (3)
H14A	0.5615	0.4393	0.6079	0.036*
H14B	0.5372	0.3606	0.7427	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0236 (5)	0.0230 (5)	0.0319 (5)	0.0007 (4)	0.0134 (4)	−0.0055 (4)
O2	0.0198 (4)	0.0193 (5)	0.0280 (5)	0.0008 (4)	0.0061 (4)	0.0010 (4)
N1	0.0248 (6)	0.0226 (6)	0.0263 (6)	−0.0051 (5)	0.0071 (5)	−0.0031 (5)
C1	0.0195 (6)	0.0260 (7)	0.0206 (6)	0.0007 (5)	0.0029 (5)	0.0009 (5)
C2	0.0297 (7)	0.0371 (9)	0.0223 (6)	0.0005 (7)	0.0042 (5)	−0.0049 (6)
C3	0.0367 (8)	0.0505 (11)	0.0229 (6)	0.0035 (8)	0.0110 (6)	0.0002 (7)
C4	0.0379 (8)	0.0461 (10)	0.0293 (7)	−0.0009 (8)	0.0171 (7)	0.0055 (7)
C5	0.0315 (7)	0.0307 (7)	0.0266 (6)	−0.0033 (7)	0.0123 (6)	0.0037 (6)
C6	0.0200 (5)	0.0221 (6)	0.0209 (6)	0.0013 (5)	0.0049 (5)	0.0021 (5)
C7	0.0188 (5)	0.0195 (6)	0.0217 (6)	0.0003 (5)	0.0069 (5)	0.0024 (5)
C8	0.0271 (6)	0.0168 (6)	0.0263 (6)	−0.0022 (5)	0.0130 (5)	0.0012 (5)
C9	0.0192 (5)	0.0169 (6)	0.0251 (6)	0.0009 (5)	0.0100 (5)	−0.0009 (5)
C10	0.0191 (6)	0.0245 (7)	0.0283 (6)	−0.0021 (5)	0.0113 (5)	0.0002 (6)
C11	0.0246 (6)	0.0212 (7)	0.0303 (7)	−0.0056 (5)	0.0128 (5)	−0.0005 (5)
C12	0.0186 (5)	0.0195 (6)	0.0239 (6)	−0.0004 (5)	0.0062 (5)	0.0009 (5)
C13	0.0284 (7)	0.0233 (7)	0.0283 (6)	−0.0032 (6)	0.0099 (6)	−0.0020 (5)
C14	0.0227 (6)	0.0304 (8)	0.0323 (7)	−0.0011 (6)	0.0065 (6)	−0.0065 (6)

O1—C9	1.4234 (17)	C7—C12	1.3639 (19)
O1—C13	1.4270 (17)	C7—C8	1.4936 (19)
O2—C9	1.4233 (16)	C8—C9	1.5358 (18)
O2—C14	1.4303 (18)	C8—H8A	0.990
N1—C1	1.3785 (19)	C8—H8B	0.990
N1—C12	1.3822 (18)	C9—C10	1.5177 (18)
N1—H1A	0.880	C10—C11	1.529 (2)
C1—C2	1.395 (2)	C10—H10A	0.990
C1—C6	1.417 (2)	C10—H10B	0.990
C2—C3	1.384 (3)	C11—C12	1.4922 (18)
C2—H2A	0.950	C11—H11A	0.990
C3—C4	1.400 (3)	C11—H11B	0.990
C3—H3A	0.950	C13—C14	1.530 (2)
C4—C5	1.383 (2)	C13—H13A	0.990
C4—H4A	0.950	C13—H13B	0.990
C5—C6	1.400 (2)	C14—H14A	0.990
C5—H5A	0.950	C14—H14B	0.990
C6—C7	1.4364 (18)
C9—O1—C13	106.42 (10)	O2—C9—C10	109.62 (11)
C9—O2—C14	106.18 (11)	O1—C9—C10	108.13 (11)
C1—N1—C12	108.84 (12)	O2—C9—C8	110.90 (10)
C1—N1—H1A	125.6	O1—C9—C8	110.32 (11)
C12—N1—H1A	125.6	C10—C9—C8	112.68 (11)
N1—C1—C2	130.52 (15)	C9—C10—C11	113.10 (11)
N1—C1—C6	107.60 (12)	C9—C10—H10A	109.0
C2—C1—C6	121.87 (14)	C11—C10—H10A	109.0
C3—C2—C1	117.59 (16)	C9—C10—H10B	109.0
C3—C2—H2A	121.2	C11—C10—H10B	109.0
C1—C2—H2A	121.2	H10A—C10—H10B	107.8
C2—C3—C4	121.30 (15)	C12—C11—C10	109.68 (12)
C2—C3—H3A	119.3	C12—C11—H11A	109.7
C4—C3—H3A	119.3	C10—C11—H11A	109.7
C5—C4—C3	121.20 (16)	C12—C11—H11B	109.7
C5—C4—H4A	119.4	C10—C11—H11B	109.7
C3—C4—H4A	119.4	H11A—C11—H11B	108.2
C4—C5—C6	118.84 (16)	C7—C12—N1	109.75 (12)
C4—C5—H5A	120.6	C7—C12—C11	125.61 (13)
C6—C5—H5A	120.6	N1—C12—C11	124.58 (13)
C5—C6—C1	119.19 (13)	O1—C13—C14	104.37 (12)
C5—C6—C7	134.15 (14)	O1—C13—H13A	110.9
C1—C6—C7	106.65 (12)	C14—C13—H13A	110.9
C12—C7—C6	107.16 (13)	O1—C13—H13B	110.9
C12—C7—C8	123.08 (12)	C14—C13—H13B	110.9
C6—C7—C8	129.75 (12)	H13A—C13—H13B	108.9
C7—C8—C9	110.64 (11)	O2—C14—C13	105.08 (11)
C7—C8—H8A	109.5	O2—C14—H14A	110.7
C9—C8—H8A	109.5	C13—C14—H14A	110.7
C7—C8—H8B	109.5	O2—C14—H14B	110.7
C9—C8—H8B	109.5	C13—C14—H14B	110.7
H8A—C8—H8B	108.1	H14A—C14—H14B	108.8
O2—C9—O1	104.87 (11)
C12—N1—C1—C2	179.41 (15)	C13—O1—C9—O2	36.02 (13)
C12—N1—C1—C6	0.36 (15)	C13—O1—C9—C10	152.93 (12)
N1—C1—C2—C3	−178.93 (15)	C13—O1—C9—C8	−83.44 (13)
C6—C1—C2—C3	0.0 (2)	C7—C8—C9—O2	79.85 (14)
C1—C2—C3—C4	0.4 (3)	C7—C8—C9—O1	−164.41 (11)
C2—C3—C4—C5	−0.6 (3)	C7—C8—C9—C10	−43.46 (16)
C3—C4—C5—C6	0.3 (3)	O2—C9—C10—C11	−64.65 (14)
C4—C5—C6—C1	0.2 (2)	O1—C9—C10—C11	−178.44 (11)
C4—C5—C6—C7	178.70 (16)	C8—C9—C10—C11	59.37 (16)
N1—C1—C6—C5	178.86 (13)	C9—C10—C11—C12	−42.89 (16)
C2—C1—C6—C5	−0.3 (2)	C6—C7—C12—N1	0.49 (15)
N1—C1—C6—C7	−0.06 (15)	C8—C7—C12—N1	179.18 (12)
C2—C1—C6—C7	−179.21 (13)	C6—C7—C12—C11	177.82 (13)
C5—C6—C7—C12	−178.94 (16)	C8—C7—C12—C11	−3.5 (2)
C1—C6—C7—C12	−0.27 (14)	C1—N1—C12—C7	−0.54 (15)
C5—C6—C7—C8	2.5 (3)	C1—N1—C12—C11	−177.90 (13)
C1—C6—C7—C8	−178.84 (13)	C10—C11—C12—C7	16.12 (19)
C12—C7—C8—C9	16.67 (18)	C10—C11—C12—N1	−166.94 (12)
C6—C7—C8—C9	−164.96 (13)	C9—O1—C13—C14	−22.68 (15)
C14—O2—C9—O1	−34.81 (13)	C9—O2—C14—C13	20.17 (14)
C14—O2—C9—C10	−150.69 (12)	O1—C13—C14—O2	1.51 (16)
C14—O2—C9—C8	84.26 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···C1i	0.88	2.72	3.527 (2)	154
C14—H14A···C12ii	0.99	2.85	3.518 (3)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯C1i	0.88	2.72	3.527 (2)	154
C14—H14A⋯C12ii	0.99	2.85	3.518 (3)	126

Symmetry codes: (i) ; (ii) .