Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title mol­ecule, C16H11BrN2O2S, the phenyl ring and mean plane of the indole ring system make a dihedral angle of 82.9 (1)°. Inter­molecular C—H...O hydrogen bonds link the mol­ecules into linear chains extended along the a axis. The crystal packing is further stabilized by van der Waals forces.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805043011/cv6622sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805043011/cv6622Isup2.hkl
Contains datablock I

CCDC reference: 298409

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.044
  • wR factor = 0.120
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low .... 0.90
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.55 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C2 - C16 ... 1.42 Ang.
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

3-Bromomethyl-1-phenylsulfonyl-1H-indole-2-carbonitrile top
Crystal data top
C16H11BrN2O2SZ = 2
Mr = 375.24F(000) = 376
Triclinic, P1Dx = 1.608 Mg m3
a = 8.2689 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9841 (15) ÅCell parameters from 6233 reflections
c = 11.805 (2) Åθ = 1.5–27.4°
α = 77.722 (3)°µ = 2.80 mm1
β = 86.703 (3)°T = 293 K
γ = 64.795 (3)°Block, yellow
V = 774.8 (2) Å30.29 × 0.21 × 0.16 mm
Data collection top
Bruker SMART APEX area-detector
diffractometer
3157 independent reflections
Radiation source: fine-focus sealed tube2493 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 27.4°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 910
Tmin = 0.499, Tmax = 0.639k = 1111
6233 measured reflectionsl = 1514
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0728P)2 + 0.1871P]
where P = (Fo2 + 2Fc2)/3
3157 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.19 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
Br10.46514 (5)0.39437 (5)0.32151 (3)0.07063 (18)
S10.03439 (10)0.34730 (10)0.21489 (8)0.0579 (2)
O10.0758 (4)0.4792 (3)0.2753 (3)0.0807 (8)
O20.1675 (3)0.3389 (4)0.1494 (3)0.0848 (9)
N10.0376 (3)0.1694 (3)0.3189 (2)0.0521 (6)
C20.0683 (4)0.0112 (4)0.2983 (3)0.0510 (7)
C30.1785 (4)0.1126 (4)0.3828 (3)0.0505 (7)
C40.2259 (4)0.0345 (4)0.4611 (3)0.0488 (7)
C50.1396 (4)0.1397 (4)0.4193 (3)0.0472 (7)
C60.1575 (5)0.2520 (5)0.4777 (3)0.0613 (9)
H60.10120.36770.44990.074*
C70.2625 (5)0.1834 (5)0.5786 (3)0.0666 (10)
H70.27630.25520.61950.080*
C80.3475 (5)0.0127 (6)0.6209 (3)0.0683 (10)
H80.41700.02800.68930.082*
C90.3310 (4)0.0989 (5)0.5632 (3)0.0593 (8)
H90.38880.21430.59180.071*
C100.1536 (4)0.3225 (4)0.1322 (3)0.0471 (7)
C110.2769 (5)0.3736 (5)0.1644 (3)0.0644 (9)
H110.25600.42810.22600.077*
C120.4302 (5)0.3426 (6)0.1038 (4)0.0769 (11)
H120.51490.37520.12500.092*
C130.4595 (6)0.2645 (6)0.0129 (4)0.0804 (12)
H130.56520.24180.02660.097*
C140.3337 (6)0.2189 (5)0.0208 (3)0.0774 (11)
H140.35310.16890.08470.093*
C150.1802 (5)0.2464 (4)0.0389 (3)0.0616 (8)
H150.09560.21430.01680.074*
C160.0129 (6)0.0121 (5)0.2043 (3)0.0686 (10)
N170.0686 (7)0.0477 (6)0.1346 (3)0.1075 (14)
C180.2333 (5)0.2945 (4)0.3918 (3)0.0604 (8)
H18A0.14410.31080.35250.073*
H18B0.24170.34980.47270.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0615 (3)0.0650 (3)0.0908 (3)0.02375 (19)0.02008 (19)0.0386 (2)
S10.0399 (4)0.0499 (5)0.0770 (6)0.0141 (3)0.0017 (4)0.0098 (4)
O10.0724 (17)0.0504 (14)0.103 (2)0.0082 (12)0.0171 (15)0.0236 (14)
O20.0439 (14)0.093 (2)0.110 (2)0.0285 (14)0.0186 (13)0.0003 (17)
N10.0502 (14)0.0501 (15)0.0620 (15)0.0261 (12)0.0082 (12)0.0153 (12)
C20.0520 (17)0.0571 (19)0.0577 (17)0.0328 (15)0.0140 (14)0.0222 (15)
C30.0466 (16)0.0501 (17)0.0621 (18)0.0242 (14)0.0186 (14)0.0226 (15)
C40.0424 (15)0.0540 (18)0.0570 (17)0.0242 (14)0.0154 (13)0.0213 (14)
C50.0393 (15)0.0523 (17)0.0569 (17)0.0229 (13)0.0157 (13)0.0215 (14)
C60.0547 (19)0.060 (2)0.083 (2)0.0309 (16)0.0225 (17)0.0352 (18)
C70.064 (2)0.085 (3)0.075 (2)0.043 (2)0.0140 (18)0.043 (2)
C80.058 (2)0.098 (3)0.060 (2)0.039 (2)0.0064 (16)0.028 (2)
C90.0495 (18)0.064 (2)0.063 (2)0.0223 (16)0.0095 (15)0.0143 (16)
C100.0427 (15)0.0423 (15)0.0538 (17)0.0181 (13)0.0044 (12)0.0032 (13)
C110.066 (2)0.080 (2)0.065 (2)0.046 (2)0.0013 (17)0.0180 (18)
C120.063 (2)0.103 (3)0.077 (3)0.055 (2)0.0003 (19)0.003 (2)
C130.066 (2)0.086 (3)0.076 (3)0.029 (2)0.019 (2)0.002 (2)
C140.101 (3)0.071 (2)0.063 (2)0.039 (2)0.020 (2)0.0191 (19)
C150.073 (2)0.058 (2)0.0601 (19)0.0350 (18)0.0023 (17)0.0092 (16)
C160.088 (3)0.081 (3)0.058 (2)0.054 (2)0.0129 (18)0.0212 (18)
N170.154 (4)0.141 (4)0.074 (2)0.099 (4)0.009 (2)0.040 (2)
C180.061 (2)0.0510 (18)0.078 (2)0.0289 (16)0.0209 (17)0.0246 (16)
Geometric parameters (Å, º) top
Br1—C181.959 (3)C8—C91.380 (5)
S1—O21.417 (3)C8—H80.9300
S1—O11.420 (3)C9—H90.9300
S1—N11.690 (3)C10—C151.376 (5)
S1—C101.744 (3)C10—C111.382 (4)
N1—C21.405 (4)C11—C121.370 (5)
N1—C51.406 (4)C11—H110.9300
C2—C31.352 (5)C12—C131.359 (6)
C2—C161.425 (5)C12—H120.9300
C3—C41.433 (4)C13—C141.374 (6)
C3—C181.480 (4)C13—H130.9300
C4—C91.392 (5)C14—C151.368 (6)
C4—C51.401 (4)C14—H140.9300
C5—C61.396 (4)C15—H150.9300
C6—C71.380 (5)C16—N171.128 (5)
C6—H60.9300C18—H18A0.9700
C7—C81.375 (6)C18—H18B0.9700
C7—H70.9300
O2—S1—O1121.29 (19)C9—C8—H8119.6
O2—S1—N1104.86 (16)C8—C9—C4118.4 (3)
O1—S1—N1105.02 (16)C8—C9—H9120.8
O2—S1—C10109.85 (17)C4—C9—H9120.8
O1—S1—C10110.64 (16)C15—C10—C11121.2 (3)
N1—S1—C10103.37 (13)C15—C10—S1119.4 (2)
C2—N1—C5106.8 (3)C11—C10—S1119.3 (3)
C2—N1—S1123.6 (2)C12—C11—C10118.8 (3)
C5—N1—S1125.2 (2)C12—C11—H11120.6
C3—C2—N1110.2 (3)C10—C11—H11120.6
C3—C2—C16125.8 (3)C13—C12—C11120.5 (4)
N1—C2—C16123.9 (3)C13—C12—H12119.8
C2—C3—C4107.6 (3)C11—C12—H12119.8
C2—C3—C18125.0 (3)C12—C13—C14120.3 (4)
C4—C3—C18127.4 (3)C12—C13—H13119.9
C9—C4—C5120.1 (3)C14—C13—H13119.9
C9—C4—C3132.7 (3)C15—C14—C13120.5 (4)
C5—C4—C3107.2 (3)C15—C14—H14119.7
C6—C5—C4121.3 (3)C13—C14—H14119.7
C6—C5—N1130.6 (3)C14—C15—C10118.6 (3)
C4—C5—N1108.1 (3)C14—C15—H15120.7
C7—C6—C5116.9 (3)C10—C15—H15120.7
C7—C6—H6121.6N17—C16—C2172.9 (5)
C5—C6—H6121.6C3—C18—Br1110.1 (2)
C8—C7—C6122.5 (3)C3—C18—H18A109.6
C8—C7—H7118.8Br1—C18—H18A109.6
C6—C7—H7118.8C3—C18—H18B109.6
C7—C8—C9120.9 (3)Br1—C18—H18B109.6
C7—C8—H8119.6H18A—C18—H18B108.1
O2—S1—N1—C241.7 (3)S1—N1—C5—C4159.0 (2)
O1—S1—N1—C2170.6 (2)C4—C5—C6—C70.5 (5)
C10—S1—N1—C273.4 (3)N1—C5—C6—C7176.9 (3)
O2—S1—N1—C5165.0 (3)C5—C6—C7—C80.3 (5)
O1—S1—N1—C536.1 (3)C6—C7—C8—C90.0 (6)
C10—S1—N1—C579.9 (3)C7—C8—C9—C40.1 (5)
C5—N1—C2—C32.0 (3)C5—C4—C9—C80.1 (4)
S1—N1—C2—C3159.5 (2)C3—C4—C9—C8178.6 (3)
C5—N1—C2—C16179.4 (3)O2—S1—C10—C1521.1 (3)
S1—N1—C2—C1623.2 (4)O1—S1—C10—C15157.6 (3)
N1—C2—C3—C41.2 (3)N1—S1—C10—C1590.4 (3)
C16—C2—C3—C4178.5 (3)O2—S1—C10—C11161.5 (3)
N1—C2—C3—C18177.2 (3)O1—S1—C10—C1124.9 (3)
C16—C2—C3—C180.1 (5)N1—S1—C10—C1187.1 (3)
C2—C3—C4—C9178.5 (3)C15—C10—C11—C122.0 (5)
C18—C3—C4—C90.1 (5)S1—C10—C11—C12175.4 (3)
C2—C3—C4—C50.1 (3)C10—C11—C12—C130.7 (6)
C18—C3—C4—C5178.5 (3)C11—C12—C13—C141.4 (7)
C9—C4—C5—C60.4 (4)C12—C13—C14—C152.2 (7)
C3—C4—C5—C6179.3 (3)C13—C14—C15—C100.8 (6)
C9—C4—C5—N1177.5 (3)C11—C10—C15—C141.3 (5)
C3—C4—C5—N11.3 (3)S1—C10—C15—C14176.1 (3)
C2—N1—C5—C6179.7 (3)C2—C3—C18—Br195.9 (3)
S1—N1—C5—C623.3 (4)C4—C3—C18—Br185.9 (3)
C2—N1—C5—C42.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O10.932.372.949 (5)120
C12—H12···O2i0.932.533.385 (6)153
Symmetry code: (i) x+1, y, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds