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In the title compound, C21H17NO4S, all bond lengths and angles show normal values. The sulfonyl-bound phenyl ring forms a dihedral angle of 88.31 (1)° with the mean plane of the carbazole fragment. The crystal packing is stabilized by weak inter­molecular π–π, C—H...π and C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037263/cv2121sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037263/cv2121Isup2.hkl
Contains datablock I

CCDC reference: 624195

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.093
  • Data-to-parameter ratio = 20.7

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.817 0.980 Tmin(prime) and Tmax expected: 0.914 0.981 RR(prime) = 0.894 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.89
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Ethyl 9-phenylsulfonylcarbazole-3-carboxylate top
Crystal data top
C21H17NO4SZ = 2
Mr = 379.42F(000) = 396
Triclinic, P1Dx = 1.451 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0912 (2) ÅCell parameters from 6119 reflections
b = 9.1704 (2) Åθ = 2.4–37.5°
c = 12.3718 (2) ŵ = 0.22 mm1
α = 78.685 (1)°T = 100 K
β = 87.567 (1)°Plate, colourless
γ = 74.694 (1)°0.41 × 0.28 × 0.09 mm
V = 868.17 (3) Å3
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
5056 independent reflections
Radiation source: fine-focus sealed tube4563 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 1.7°
ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1212
Tmin = 0.817, Tmax = 0.980l = 1717
27950 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0488P)2 + 0.3804P]
where P = (Fo2 + 2Fc2)/3
5056 reflections(Δ/σ)max = 0.001
244 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.42 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
S10.78637 (3)0.40273 (3)0.32359 (2)0.01342 (7)
O10.95002 (10)0.29365 (10)0.34244 (7)0.01804 (16)
O20.74032 (11)0.52807 (10)0.38165 (7)0.01843 (17)
O30.93350 (11)0.32261 (9)0.28004 (6)0.01774 (16)
O41.11691 (12)0.10823 (10)0.18851 (7)0.02258 (18)
N10.77665 (12)0.48005 (10)0.19029 (7)0.01402 (17)
C10.64361 (13)0.61046 (12)0.14092 (9)0.01348 (19)
C20.53211 (15)0.72427 (13)0.18830 (9)0.0175 (2)
H20.53400.72240.26530.021*
C30.41795 (15)0.84063 (13)0.11784 (10)0.0193 (2)
H30.34000.91940.14780.023*
C40.41420 (15)0.84537 (13)0.00424 (10)0.0186 (2)
H40.33450.92650.04150.022*
C50.52669 (14)0.73178 (12)0.04168 (9)0.0165 (2)
H50.52560.73470.11880.020*
C60.64132 (13)0.61330 (12)0.02730 (9)0.01356 (19)
C70.77117 (13)0.48053 (12)0.00508 (8)0.01283 (18)
C80.82348 (14)0.42954 (12)0.09259 (9)0.01397 (19)
H80.77290.48640.16120.017*
C90.95184 (13)0.29306 (12)0.08750 (8)0.01383 (19)
C101.02671 (14)0.21025 (12)0.01378 (9)0.0160 (2)
H101.11270.11650.01540.019*
C110.97894 (14)0.26122 (13)0.11181 (9)0.0163 (2)
H111.03190.20540.18000.020*
C120.85013 (13)0.39760 (12)0.10600 (8)0.01314 (19)
C130.62604 (13)0.30320 (12)0.34371 (8)0.01402 (19)
C140.66329 (15)0.15356 (13)0.32336 (9)0.0181 (2)
H140.77410.10530.30000.022*
C150.53482 (17)0.07667 (14)0.33805 (10)0.0225 (2)
H150.55770.02560.32520.027*
C160.37264 (17)0.14918 (15)0.37150 (11)0.0243 (2)
H160.28530.09600.38110.029*
C170.33706 (16)0.29835 (15)0.39096 (11)0.0237 (2)
H170.22570.34700.41330.028*
C180.46444 (14)0.37670 (13)0.37775 (10)0.0187 (2)
H180.44170.47840.39170.022*
C191.01124 (14)0.22968 (12)0.18831 (9)0.01502 (19)
C200.97629 (16)0.26535 (13)0.38163 (9)0.0188 (2)
H20A1.10040.21430.38200.023*
H20B0.95050.35260.44510.023*
C210.87510 (17)0.15185 (15)0.39290 (10)0.0229 (2)
H21A0.90550.11430.46190.034*
H21B0.75230.20290.39350.034*
H21C0.90200.06480.33060.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01102 (12)0.01807 (13)0.01180 (12)0.00389 (9)0.00000 (8)0.00417 (9)
O10.0112 (4)0.0257 (4)0.0154 (4)0.0023 (3)0.0018 (3)0.0027 (3)
O20.0195 (4)0.0225 (4)0.0166 (4)0.0076 (3)0.0016 (3)0.0089 (3)
O30.0223 (4)0.0171 (4)0.0123 (3)0.0014 (3)0.0007 (3)0.0044 (3)
O40.0230 (4)0.0208 (4)0.0198 (4)0.0042 (3)0.0010 (3)0.0076 (3)
N10.0129 (4)0.0156 (4)0.0125 (4)0.0014 (3)0.0009 (3)0.0036 (3)
C10.0108 (4)0.0139 (4)0.0158 (5)0.0033 (3)0.0005 (3)0.0030 (4)
C20.0166 (5)0.0176 (5)0.0187 (5)0.0034 (4)0.0029 (4)0.0065 (4)
C30.0161 (5)0.0160 (5)0.0248 (5)0.0013 (4)0.0033 (4)0.0063 (4)
C40.0151 (5)0.0143 (5)0.0239 (5)0.0005 (4)0.0001 (4)0.0023 (4)
C50.0152 (5)0.0159 (5)0.0171 (5)0.0025 (4)0.0004 (4)0.0020 (4)
C60.0110 (4)0.0136 (4)0.0163 (5)0.0030 (4)0.0010 (3)0.0037 (4)
C70.0105 (4)0.0133 (4)0.0145 (4)0.0026 (3)0.0001 (3)0.0027 (3)
C80.0132 (5)0.0146 (4)0.0136 (4)0.0029 (4)0.0001 (3)0.0027 (3)
C90.0133 (5)0.0145 (4)0.0139 (4)0.0030 (4)0.0013 (3)0.0040 (4)
C100.0141 (5)0.0158 (5)0.0162 (5)0.0001 (4)0.0000 (4)0.0037 (4)
C110.0148 (5)0.0174 (5)0.0137 (4)0.0002 (4)0.0007 (4)0.0019 (4)
C120.0112 (4)0.0153 (4)0.0133 (4)0.0035 (4)0.0012 (3)0.0037 (3)
C130.0124 (5)0.0172 (5)0.0127 (4)0.0043 (4)0.0005 (3)0.0028 (4)
C140.0165 (5)0.0181 (5)0.0190 (5)0.0022 (4)0.0009 (4)0.0050 (4)
C150.0252 (6)0.0184 (5)0.0253 (6)0.0077 (4)0.0032 (5)0.0039 (4)
C160.0220 (6)0.0266 (6)0.0271 (6)0.0132 (5)0.0015 (5)0.0020 (5)
C170.0149 (5)0.0282 (6)0.0287 (6)0.0075 (5)0.0037 (4)0.0057 (5)
C180.0144 (5)0.0191 (5)0.0226 (5)0.0035 (4)0.0023 (4)0.0057 (4)
C190.0144 (5)0.0159 (5)0.0148 (5)0.0035 (4)0.0008 (4)0.0037 (4)
C200.0241 (6)0.0206 (5)0.0126 (4)0.0060 (4)0.0027 (4)0.0056 (4)
C210.0275 (6)0.0245 (6)0.0187 (5)0.0089 (5)0.0003 (4)0.0062 (4)
Geometric parameters (Å, º) top
S1—O11.4296 (8)C9—C101.4006 (15)
S1—O21.4321 (8)C9—C191.4868 (14)
S1—N11.6587 (9)C10—C111.3879 (14)
S1—C131.7568 (11)C10—H100.95
O3—C191.3446 (13)C11—C121.3923 (14)
O3—C201.4496 (13)C11—H110.95
O4—C191.2123 (13)C13—C181.3930 (15)
N1—C121.4255 (13)C13—C141.3958 (15)
N1—C11.4323 (14)C14—C151.3897 (16)
C1—C21.3946 (14)C14—H140.95
C1—C61.4016 (14)C15—C161.3916 (19)
C2—C31.3910 (16)C15—H150.95
C2—H20.95C16—C171.3884 (18)
C3—C41.3989 (16)C16—H160.95
C3—H30.95C17—C181.3914 (16)
C4—C51.3871 (15)C17—H170.95
C4—H40.95C18—H180.95
C5—C61.3930 (15)C20—C211.5131 (17)
C5—H50.95C20—H20A0.99
C6—C71.4468 (14)C20—H20B0.99
C7—C81.3899 (14)C21—H21A0.98
C7—C121.4086 (14)C21—H21B0.98
C8—C91.3919 (14)C21—H21C0.98
C8—H80.95
O1—S1—O2120.11 (5)C10—C11—C12117.18 (10)
O1—S1—N1106.33 (5)C10—C11—H11121.4
O2—S1—N1106.69 (5)C12—C11—H11121.4
O1—S1—C13108.88 (5)C11—C12—C7121.57 (9)
O2—S1—C13108.70 (5)C11—C12—N1130.42 (10)
N1—S1—C13105.11 (5)C7—C12—N1108.00 (9)
C19—O3—C20115.84 (9)C18—C13—C14121.82 (10)
C12—N1—C1107.87 (8)C18—C13—S1119.11 (8)
C12—N1—S1124.09 (7)C14—C13—S1119.07 (8)
C1—N1—S1123.73 (7)C15—C14—C13118.59 (11)
C2—C1—C6121.55 (10)C15—C14—H14120.7
C2—C1—N1130.19 (10)C13—C14—H14120.7
C6—C1—N1108.23 (9)C14—C15—C16120.12 (11)
C3—C2—C1117.04 (10)C14—C15—H15119.9
C3—C2—H2121.5C16—C15—H15119.9
C1—C2—H2121.5C17—C16—C15120.71 (11)
C2—C3—C4122.14 (10)C17—C16—H16119.6
C2—C3—H3118.9C15—C16—H16119.6
C4—C3—H3118.9C16—C17—C18120.04 (11)
C5—C4—C3120.10 (11)C16—C17—H17120.0
C5—C4—H4119.9C18—C17—H17120.0
C3—C4—H4119.9C17—C18—C13118.73 (11)
C4—C5—C6118.85 (10)C17—C18—H18120.6
C4—C5—H5120.6C13—C18—H18120.6
C6—C5—H5120.6O4—C19—O3123.53 (10)
C5—C6—C1120.31 (10)O4—C19—C9124.33 (10)
C5—C6—C7131.87 (10)O3—C19—C9112.14 (9)
C1—C6—C7107.82 (9)O3—C20—C21110.53 (9)
C8—C7—C12120.42 (9)O3—C20—H20A109.5
C8—C7—C6131.62 (10)C21—C20—H20A109.5
C12—C7—C6107.96 (9)O3—C20—H20B109.5
C7—C8—C9118.37 (10)C21—C20—H20B109.5
C7—C8—H8120.8H20A—C20—H20B108.1
C9—C8—H8120.8C20—C21—H21A109.5
C8—C9—C10120.52 (9)C20—C21—H21B109.5
C8—C9—C19121.30 (10)H21A—C21—H21B109.5
C10—C9—C19118.17 (9)C20—C21—H21C109.5
C11—C10—C9121.91 (10)H21A—C21—H21C109.5
C11—C10—H10119.0H21B—C21—H21C109.5
C9—C10—H10119.0
O1—S1—N1—C1235.55 (10)C10—C11—C12—C70.09 (16)
O2—S1—N1—C12164.87 (8)C10—C11—C12—N1178.52 (10)
C13—S1—N1—C1279.81 (9)C8—C7—C12—C111.59 (16)
O1—S1—N1—C1170.64 (8)C6—C7—C12—C11178.67 (10)
O2—S1—N1—C141.32 (10)C8—C7—C12—N1177.30 (9)
C13—S1—N1—C174.00 (9)C6—C7—C12—N12.44 (11)
C12—N1—C1—C2178.65 (11)C1—N1—C12—C11177.78 (11)
S1—N1—C1—C221.24 (16)S1—N1—C12—C1120.46 (16)
C12—N1—C1—C63.18 (11)C1—N1—C12—C73.47 (11)
S1—N1—C1—C6160.59 (8)S1—N1—C12—C7160.78 (8)
C6—C1—C2—C30.21 (16)O1—S1—C13—C18152.04 (9)
N1—C1—C2—C3178.17 (10)O2—S1—C13—C1819.54 (10)
C1—C2—C3—C40.35 (17)N1—S1—C13—C1894.38 (9)
C2—C3—C4—C50.03 (18)O1—S1—C13—C1429.03 (10)
C3—C4—C5—C60.55 (17)O2—S1—C13—C14161.52 (9)
C4—C5—C6—C10.69 (16)N1—S1—C13—C1484.56 (9)
C4—C5—C6—C7179.67 (11)C18—C13—C14—C150.20 (17)
C2—C1—C6—C50.31 (16)S1—C13—C14—C15179.11 (9)
N1—C1—C6—C5178.05 (9)C13—C14—C15—C160.52 (18)
C2—C1—C6—C7179.98 (10)C14—C15—C16—C170.22 (19)
N1—C1—C6—C71.66 (11)C15—C16—C17—C180.4 (2)
C5—C6—C7—C80.4 (2)C16—C17—C18—C130.71 (19)
C1—C6—C7—C8179.23 (11)C14—C13—C18—C170.41 (17)
C5—C6—C7—C12179.84 (11)S1—C13—C18—C17178.49 (9)
C1—C6—C7—C120.48 (12)C20—O3—C19—O43.28 (16)
C12—C7—C8—C91.71 (15)C20—O3—C19—C9176.47 (9)
C6—C7—C8—C9178.61 (10)C8—C9—C19—O4176.61 (11)
C7—C8—C9—C100.42 (16)C10—C9—C19—O42.35 (17)
C7—C8—C9—C19178.52 (9)C8—C9—C19—O33.13 (14)
C8—C9—C10—C111.09 (17)C10—C9—C19—O3177.90 (9)
C19—C9—C10—C11179.93 (10)C19—O3—C20—C2180.45 (12)
C9—C10—C11—C121.23 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···Cg1i0.952.913.8605 (12)174
C14—H14···O4ii0.952.563.2826 (15)133
C2—H2···O20.952.382.9750 (14)120
C11—H11···O10.952.322.9196 (14)121
C18—H18···O20.952.572.9297 (15)103
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y, z.
 

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