9-(Phenyl­sulfon­yl)-9H-carbazol-2-ol

The crystal structure of the title mol­ecule, C₁₉H₁₃NO₃S, confirms the structure of this compound formed from a Diels-Alder reaction between 3-nitro-1-(phenyl­sulfon­yl)indole and 1-meth­oxy-3-(trimethyl­siloxy)-1,3-butadiene (Danishefsky's diene). The angle between planes of tthe carbazole ring system and the phenylsulfonyl ring is 89.97 (17)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.056
• wR factor = 0.191
• Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT073_ALERT_1_A H-atoms ref, but _hydrogen_treatment reported as     constr

Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         38 Perc.
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ......       1.50 Sigma

Alert level C
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

9-(Phenylsulfonyl)-9H-carbazol-2-ol

Crystal data

C18H13NO3S	F(000) = 1344
Mr = 323.35	Dx = 1.443 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 19 reflections
a = 18.469 (9) Å	θ = 6.2–7.4°
b = 8.392 (6) Å	µ = 0.23 mm^−1
c = 19.240 (12) Å	T = 296 K
β = 93.58 (4)°	Prism, yellow
V = 2976 (3) Å^3	0.50 × 0.50 × 0.20 mm
Z = 8

Data collection

Rigaku AFC-6S diffractometer	1307 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 27.5°, θmin = 2.1°
ω/2θ scans	h = 0→23
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.893, Tmax = 0.955	l = −24→24
3419 measured reflections	3 standard reflections every 150 reflections
3419 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.191	w = 1/[σ^2(Fo^2) + (0.0359P)^2 + 12.9406P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
3419 reflections	Δρmax = 0.29 e Å^−3
214 parameters	Δρmin = −0.37 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0003 (2)

Special details

Experimental. IR (film): λ_max 3347 (OH), 1367 (SO₂), 1176 (SO₂) cm^-1; UV (EtOH) λ_max 224, 260 nm; ¹H NMR (CD₃COCD₃, δ, p.p.m.): 8.84 (s, 1H), 8.27 (d, 1H, J = 8 Hz), 7.84–7.91 (m, 5H), 7.34–7.59 (m, 5H), 6.95 (dd, 1H, J = 2 and 8 Hz); ¹³C NMR (CD₃COCD₃, δ, p.p.m.): 158.7, 140.7, 139.0, 138.6, 135.2, 130.3, 127.8, 127.3, 126.8, 125.2, 122.0, 120.2, 119.8, 115.7, 113.9, 102.5.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.83514 (7)	0.44475 (17)	0.20267 (7)	0.0388 (4)
O1	0.78598 (19)	0.4092 (5)	0.25459 (17)	0.0490 (11)
O2	0.8836 (2)	0.5777 (5)	0.2118 (2)	0.0526 (11)
O3	0.5653 (2)	0.1511 (5)	0.1487 (2)	0.0557 (12)
N1	0.7854 (2)	0.4793 (5)	0.1296 (2)	0.0384 (11)
C1	0.6752 (3)	0.3068 (7)	0.1490 (3)	0.0394 (14)
H1	0.6851	0.2934	0.1966	0.047*
C2	0.6141 (3)	0.2389 (7)	0.1143 (3)	0.0404 (14)
C3	0.5984 (3)	0.2621 (7)	0.0442 (3)	0.0465 (15)
H2	0.5569	0.2170	0.0227	0.056*
C4	0.6432 (3)	0.3503 (7)	0.0062 (3)	0.0444 (15)
H3	0.6320	0.3664	−0.0410	0.053*
C5	0.7057 (3)	0.4167 (6)	0.0380 (3)	0.0352 (12)
C6	0.7642 (3)	0.5132 (6)	0.0123 (3)	0.0365 (13)
C7	0.7768 (3)	0.5704 (7)	−0.0531 (3)	0.0462 (14)
H4	0.7447	0.5478	−0.0909	0.055*
C8	0.8375 (3)	0.6610 (8)	−0.0616 (3)	0.0536 (17)
H5	0.8462	0.7019	−0.1053	0.064*
C9	0.8864 (3)	0.6920 (8)	−0.0047 (3)	0.0573 (17)
H6	0.9275	0.7527	−0.0114	0.069*
C10	0.8755 (3)	0.6362 (7)	0.0603 (3)	0.0473 (15)
H7	0.9085	0.6572	0.0977	0.057*
C11	0.8134 (3)	0.5467 (6)	0.0687 (3)	0.0359 (12)
C12	0.7201 (3)	0.3945 (6)	0.1093 (3)	0.0366 (13)
C13	0.8869 (3)	0.2736 (7)	0.1880 (2)	0.0334 (12)
C14	0.8576 (3)	0.1266 (7)	0.2002 (3)	0.0396 (13)
H8	0.8118	0.1191	0.2175	0.047*
C15	0.8956 (3)	−0.0096 (7)	0.1868 (3)	0.0496 (16)
H9	0.8758	−0.1095	0.1944	0.059*
C16	0.9640 (3)	0.0048 (8)	0.1618 (3)	0.0571 (17)
H10	0.9903	−0.0864	0.1526	0.068*
C17	0.9936 (3)	0.1525 (8)	0.1506 (3)	0.0564 (17)
H11	1.0399	0.1596	0.1344	0.068*
C18	0.9557 (3)	0.2896 (8)	0.1629 (3)	0.0434 (14)
H12	0.9753	0.3895	0.1548	0.052*
H13	0.583 (3)	0.134 (7)	0.190 (3)	0.06 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0409 (8)	0.0410 (8)	0.0336 (7)	0.0034 (7)	−0.0042 (6)	−0.0071 (7)
O1	0.048 (2)	0.069 (3)	0.0307 (19)	0.009 (2)	0.0068 (17)	−0.0080 (19)
O2	0.060 (2)	0.039 (2)	0.057 (3)	−0.010 (2)	−0.015 (2)	−0.010 (2)
O3	0.039 (2)	0.069 (3)	0.059 (3)	−0.005 (2)	−0.002 (2)	0.016 (2)
N1	0.039 (3)	0.043 (3)	0.033 (2)	−0.001 (2)	−0.0035 (19)	−0.001 (2)
C1	0.036 (3)	0.050 (4)	0.032 (3)	0.004 (3)	0.000 (2)	−0.002 (3)
C2	0.032 (3)	0.046 (4)	0.044 (3)	0.007 (3)	0.008 (2)	0.008 (3)
C3	0.029 (3)	0.059 (4)	0.051 (4)	−0.003 (3)	−0.004 (3)	0.004 (3)
C4	0.038 (3)	0.057 (4)	0.036 (3)	0.009 (3)	−0.010 (2)	0.001 (3)
C5	0.035 (3)	0.037 (3)	0.033 (3)	0.009 (3)	0.000 (2)	0.002 (2)
C6	0.035 (3)	0.035 (3)	0.039 (3)	0.009 (2)	0.004 (2)	0.000 (2)
C7	0.041 (3)	0.055 (4)	0.041 (3)	0.002 (3)	−0.005 (2)	0.000 (3)
C8	0.054 (4)	0.067 (5)	0.040 (3)	−0.004 (3)	0.008 (3)	0.017 (3)
C9	0.043 (4)	0.061 (4)	0.068 (4)	−0.006 (3)	0.004 (3)	0.013 (4)
C10	0.039 (3)	0.047 (4)	0.055 (4)	−0.003 (3)	−0.007 (3)	0.008 (3)
C11	0.036 (3)	0.032 (3)	0.039 (3)	0.007 (3)	−0.002 (2)	−0.002 (3)
C12	0.030 (3)	0.036 (3)	0.043 (3)	0.012 (2)	−0.002 (2)	0.000 (2)
C13	0.035 (3)	0.043 (3)	0.022 (2)	0.000 (3)	0.001 (2)	−0.001 (2)
C14	0.029 (3)	0.049 (4)	0.041 (3)	0.001 (3)	0.008 (2)	0.003 (3)
C15	0.055 (4)	0.041 (4)	0.053 (4)	0.000 (3)	0.008 (3)	0.010 (3)
C16	0.059 (4)	0.062 (5)	0.050 (4)	0.024 (3)	0.003 (3)	0.000 (3)
C17	0.035 (3)	0.077 (5)	0.059 (4)	0.008 (4)	0.013 (3)	0.007 (4)
C18	0.035 (3)	0.051 (4)	0.044 (3)	−0.007 (3)	0.003 (3)	0.008 (3)

Geometric parameters (Å, º)

S1—O1	1.423 (4)	C7—C8	1.373 (8)
S1—O2	1.434 (4)	C7—H4	0.9300
S1—N1	1.657 (4)	C8—C9	1.400 (8)
S1—C13	1.758 (5)	C8—H5	0.9300
O3—C2	1.367 (6)	C9—C10	1.361 (8)
O3—H13	0.86 (6)	C9—H6	0.9300
N1—C11	1.425 (6)	C10—C11	1.390 (7)
N1—C12	1.434 (6)	C10—H7	0.9300
C1—C12	1.375 (7)	C13—C14	1.374 (7)
C1—C2	1.398 (7)	C13—C18	1.394 (7)
C1—H1	0.9300	C14—C15	1.374 (7)
C2—C3	1.374 (7)	C14—H8	0.9300
C3—C4	1.356 (7)	C15—C16	1.384 (8)
C3—H2	0.9300	C15—H9	0.9300
C4—C5	1.390 (7)	C16—C17	1.377 (9)
C4—H3	0.9300	C16—H10	0.9300
C5—C12	1.394 (7)	C17—C18	1.375 (8)
C5—C6	1.459 (7)	C17—H11	0.9300
C6—C7	1.381 (7)	C18—H12	0.9300
C6—C11	1.400 (7)
O1—S1—O2	119.9 (2)	C7—C8—H5	120.0
O1—S1—N1	106.8 (2)	C9—C8—H5	120.0
O2—S1—N1	106.0 (2)	C10—C9—C8	122.0 (6)
O1—S1—C13	108.6 (2)	C10—C9—H6	119.0
O2—S1—C13	108.3 (2)	C8—C9—H6	119.0
N1—S1—C13	106.5 (2)	C9—C10—C11	117.6 (5)
C2—O3—H13	109 (4)	C9—C10—H7	121.2
C11—N1—C12	108.4 (4)	C11—C10—H7	121.2
C11—N1—S1	123.8 (3)	C10—C11—C6	121.3 (5)
C12—N1—S1	123.8 (4)	C10—C11—N1	130.9 (5)
C12—C1—C2	116.7 (5)	C6—C11—N1	107.8 (4)
C12—C1—H1	121.6	C1—C12—C5	122.3 (5)
C2—C1—H1	121.6	C1—C12—N1	129.8 (5)
O3—C2—C3	116.5 (5)	C5—C12—N1	107.8 (4)
O3—C2—C1	121.7 (5)	C14—C13—C18	121.6 (5)
C3—C2—C1	121.7 (5)	C14—C13—S1	118.8 (4)
C4—C3—C2	120.5 (5)	C18—C13—S1	119.6 (5)
C4—C3—H2	119.7	C13—C14—C15	120.2 (5)
C2—C3—H2	119.7	C13—C14—H8	119.9
C3—C4—C5	120.0 (5)	C15—C14—H8	119.9
C3—C4—H3	120.0	C14—C15—C16	118.7 (6)
C5—C4—H3	120.0	C14—C15—H9	120.6
C4—C5—C12	118.7 (5)	C16—C15—H9	120.6
C4—C5—C6	133.3 (5)	C17—C16—C15	120.9 (6)
C12—C5—C6	107.9 (4)	C17—C16—H10	119.6
C7—C6—C11	119.9 (5)	C15—C16—H10	119.6
C7—C6—C5	132.2 (5)	C18—C17—C16	121.0 (5)
C11—C6—C5	107.9 (4)	C18—C17—H11	119.5
C8—C7—C6	119.2 (5)	C16—C17—H11	119.5
C8—C7—H4	120.4	C17—C18—C13	117.6 (6)
C6—C7—H4	120.4	C17—C18—H12	121.2
C7—C8—C9	120.0 (5)	C13—C18—H12	121.2