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ISSN: 2056-9890

Ethyl 2-(bromo­meth­yl)-5-meth­­oxy-1-phenyl­sulfonyl-1H-indole-3-carboxyl­ate

aDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and cDepartment of Physics, Presidency College, Chennai 600 005, India
*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 11 March 2008; accepted 17 March 2008; online 20 March 2008)

In the title compound, C19H18BrNO5S, the plane of the phenyl ring forms a dihedral angle of 76.99 (6)° with the indole ring system. The Br atom is disordered over two positions, with site-occupancy factors of 0.833 (14) and 0.167 (14). The mol­ecular structure is stabilized by weak intra­molecular C—H⋯O inter­actions and the crystal packing is stabilized by weak inter­molecular C—H⋯O inter­actions.

Related literature

For biological activity, see: Nieto et al. (2005[Nieto, M. J., Alovero, F. L., Manzo, R. H. & Mazzieri, M. R. (2005). Eur. J. Med. Chem. 40, 361-369.]); Yang et al. (2002[Yang, L. M., Lin, S. J., Hsu, F. L. & Yang, T. H. (2002). Bioorg. Med. Chem. Lett. 12, 1013-1015.]). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007[Chakkaravarthi, G., Ramesh, N., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3564.], 2008[Chakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18BrNO5S

  • Mr = 452.31

  • Triclinic, [P \overline 1]

  • a = 8.9988 (3) Å

  • b = 9.2343 (2) Å

  • c = 11.6068 (3) Å

  • α = 82.524 (1)°

  • β = 87.666 (2)°

  • γ = 84.942 (3)°

  • V = 952.16 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.30 mm−1

  • T = 295 (2) K

  • 0.20 × 0.20 × 0.16 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.593, Tmax = 0.692

  • 25160 measured reflections

  • 6169 independent reflections

  • 4163 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.127

  • S = 1.03

  • 6169 reflections

  • 254 parameters

  • 3 restraints

  • H-atom parameters constrained

  • Δρmax = 0.68 e Å−3

  • Δρmin = −0.89 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C12—H12⋯O1i 0.93 2.56 3.472 (3) 165
C2—H2⋯O5ii 0.93 2.60 3.235 (3) 126
C6—H6⋯O2 0.93 2.54 2.908 (4) 104
C10—H10⋯O4 0.93 2.37 2.892 (3) 116
C13—H13⋯O1 0.93 2.28 2.863 (3) 120
C15—H15A⋯O5 0.97 2.31 2.911 (4) 119
C15—H15D⋯O2 0.97 2.16 2.895 (4) 131
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In continuation of our studies of benzenesulfonamide derivatives, which are known to exhibit anti–bacterial (Nieto et al., 2005) anti–tumour (Yang et al., 2002) activities, we report the crystal structure of the title compound (I). The geometric parameters of the molecule of I (Fig. 1) agree well with the reported structures (Chakkaravarthi et al., 2007; Chakkaravarthi et al., 2008).

The plane of the phenyl ring forms a dihedral angle of 76.99 (6)° with the indole ring system. The N1—S1—C1 plane is orthogonal to indole ring (dihedral angle 88.70 (7)°) and makes 75.97 (9)° with the phenyl ring. The plane of indole ring is almost coplanar (dihedral angle 2.66 (7)°) with the ester group and makes 6.33 (18)° with the methoxy group.

The torsion angles O2–S1–N1–C7 and O1–S1–N1–C14 [-30.0 (2)° and 27.3 (2)°, respectively] indicate syn–conformation of the sulfonyl moiety. The Br1 atom is disordered over two positions with the site occupancy factors of 0.833 (14) and 0.167 (14). The molecular packing is stabilized by weak intramolecular C—H···O interactions and the crystal packing of I (Fig. 2) is stabilized by weak intermolecular C—H···O interactions (see Table).

Related literature top

For biological activity, see: Nieto et al. (2005); Yang et al. (2002). For the structures of closely related compounds, see: Chakkaravarthi et al. (2007, 2008).

Experimental top

Ethyl 2-(methyl)-5-methoxy-1-(phenylsulfonyl)-1H-indole-3-carboxylate (1g, 2.2 mmol), N–bromo succinimide (0.4 g, 2.3 mmol), azo–bis–isobutyronitrile (50 mg) were dissolved in 50 ml of carbon tetrachloride. Refluxed on a waterbath for 2hr. Cooled to room temperature. Succinimide was filtered off over sodium sulfate. Filtrate was evaporated under reduced pressure. Product was recrystallized from methanol. Yield: 78%.

Refinement top

The H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2 and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3. The site occupancy factors for disordered Br atom is refined as Br1= 0.833 (14) and Br1A = 0.167 (14) during anisotropic refinement. The C15—Br1A distance was restrained to 1.91 (10) Å. The anisotropic displacement parameters of Br1 and Br1A were set equal by the command EADP and the anisotropic thermal parameters of C4, C5, C15 and Br1A atoms were restrained with DELU in the final cycles of refinement (Sheldrick, 2008).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of I, with atom labeling scheme. Displacement ellipsoids are drawn at 50% probability level. H atoms are presented as a small spheres of arbitrary radius. Only major fragment for disordered Br1 and C15 are drawn. Intramolecular H–bonds are shown as dashed lines.
[Figure 2] Fig. 2. The packing of I, viewed down the a axis. Intermolecular H–bonds are shown as dashed lines H atoms not involving hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y+1, z].
Ethyl 2-(bromomethyl)-5-methoxy-1-phenylsulfonyl-1H-indole-3-carboxylate top
Crystal data top
C19H18BrNO5SZ = 2
Mr = 452.31F(000) = 460
Triclinic, P1Dx = 1.578 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9988 (3) ÅCell parameters from 8207 reflections
b = 9.2343 (2) Åθ = 2.2–27.5°
c = 11.6068 (3) ŵ = 2.30 mm1
α = 82.524 (1)°T = 295 K
β = 87.666 (2)°Block, colourless
γ = 84.942 (3)°0.20 × 0.20 × 0.16 mm
V = 952.16 (5) Å3
Data collection top
Bruker Kappa APEXII
diffractometer
6169 independent reflections
Radiation source: Fine–focus sealed tube4163 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω and ϕ scansθmax = 31.2°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1313
Tmin = 0.593, Tmax = 0.692k = 1313
25160 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: Direct
Least-squares matrix: FullSecondary atom site location: Difmap
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: Geom
wR(F2) = 0.127H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.054P)2 + 0.4811P]
where P = (Fo2 + 2Fc2)/3
6169 reflections(Δ/σ)max < 0.001
254 parametersΔρmax = 0.68 e Å3
3 restraintsΔρmin = 0.89 e Å3
Crystal data top
C19H18BrNO5Sγ = 84.942 (3)°
Mr = 452.31V = 952.16 (5) Å3
Triclinic, P1Z = 2
a = 8.9988 (3) ÅMo Kα radiation
b = 9.2343 (2) ŵ = 2.30 mm1
c = 11.6068 (3) ÅT = 295 K
α = 82.524 (1)°0.20 × 0.20 × 0.16 mm
β = 87.666 (2)°
Data collection top
Bruker Kappa APEXII
diffractometer
6169 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4163 reflections with I > 2σ(I)
Tmin = 0.593, Tmax = 0.692Rint = 0.027
25160 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0443 restraints
wR(F2) = 0.127H-atom parameters constrained
S = 1.04Δρmax = 0.68 e Å3
6169 reflectionsΔρmin = 0.89 e Å3
254 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Br10.2859 (3)0.0105 (2)0.5880 (3)0.0695 (4)0.833 (14)
Br1A0.2613 (8)0.0063 (7)0.6105 (7)0.0695 (4)0.167 (14)
S10.53695 (6)0.26331 (6)0.73409 (5)0.04656 (14)
O10.6066 (2)0.3534 (2)0.80232 (18)0.0623 (5)
O20.6249 (2)0.1714 (2)0.66452 (19)0.0688 (6)
O30.1927 (3)0.2237 (2)1.26357 (17)0.0714 (6)
O40.1493 (2)0.18350 (18)1.02343 (16)0.0551 (4)
O50.2440 (3)0.2589 (2)0.8592 (2)0.0783 (6)
N10.4384 (2)0.15286 (19)0.82973 (15)0.0410 (4)
C10.4041 (2)0.3722 (2)0.64784 (18)0.0407 (4)
C20.3253 (3)0.4881 (3)0.6931 (2)0.0499 (5)
H20.34050.50620.76860.060*
C30.2243 (3)0.5759 (3)0.6245 (3)0.0627 (7)
H30.17030.65450.65370.075*
C40.2020 (4)0.5490 (3)0.5135 (3)0.0690 (7)
H40.13210.60850.46820.083*
C50.2818 (4)0.4352 (3)0.4690 (2)0.0693 (7)
H50.26630.41780.39350.083*
C60.3860 (3)0.3453 (3)0.5360 (2)0.0561 (6)
H60.44220.26880.50580.067*
C70.3878 (2)0.0171 (2)0.81460 (18)0.0412 (4)
C80.3026 (2)0.0297 (2)0.90984 (18)0.0393 (4)
C90.2973 (2)0.0781 (2)0.98934 (17)0.0380 (4)
C100.2300 (3)0.0839 (3)1.10015 (19)0.0452 (5)
H100.17420.00931.13530.054*
C110.2498 (3)0.2044 (3)1.1549 (2)0.0510 (5)
C120.3333 (3)0.3160 (3)1.1024 (2)0.0555 (6)
H120.34440.39581.14170.067*
C130.3993 (3)0.3117 (3)0.9951 (2)0.0516 (5)
H130.45470.38710.96070.062*
C140.3808 (2)0.1902 (2)0.93842 (18)0.0399 (4)
C150.4242 (3)0.0591 (3)0.7108 (2)0.0560 (5)
H15A0.42870.16400.73460.067*0.833 (14)
H15B0.52260.03560.68080.067*0.833 (14)
H15C0.43020.16460.73120.067*0.167 (14)
H15D0.51760.03060.67360.067*0.167 (14)
C160.0958 (4)0.1221 (4)1.3175 (3)0.0719 (8)
H16A0.01090.12211.27000.108*
H16B0.06300.14871.39220.108*
H16C0.14740.02591.32710.108*
C170.2311 (3)0.1686 (2)0.9262 (2)0.0470 (5)
C180.0781 (3)0.3188 (3)1.0520 (3)0.0738 (9)
H18A0.15070.40231.04880.089*
H18B0.00080.32430.99720.089*
C190.0120 (4)0.3191 (5)1.1716 (4)0.1037 (15)
H19A0.08960.31501.22520.156*
H19B0.03750.40701.19300.156*
H19C0.05890.23541.17390.156*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0960 (5)0.0791 (4)0.0381 (5)0.0300 (4)0.0142 (5)0.0064 (4)
Br1A0.0960 (5)0.0791 (4)0.0381 (5)0.0300 (4)0.0142 (5)0.0064 (4)
S10.0417 (3)0.0457 (3)0.0503 (3)0.0032 (2)0.0003 (2)0.0003 (2)
O10.0509 (10)0.0655 (11)0.0719 (12)0.0198 (8)0.0153 (8)0.0002 (9)
O20.0616 (11)0.0617 (11)0.0763 (13)0.0099 (9)0.0226 (10)0.0013 (10)
O30.0890 (15)0.0806 (14)0.0485 (10)0.0023 (11)0.0037 (10)0.0285 (10)
O40.0634 (10)0.0476 (9)0.0544 (10)0.0169 (8)0.0054 (8)0.0019 (7)
O50.1144 (18)0.0565 (11)0.0729 (13)0.0309 (11)0.0018 (12)0.0271 (10)
N10.0493 (10)0.0366 (8)0.0368 (9)0.0027 (7)0.0047 (7)0.0028 (7)
C10.0475 (11)0.0364 (10)0.0378 (10)0.0087 (8)0.0007 (8)0.0004 (8)
C20.0592 (14)0.0448 (12)0.0446 (12)0.0003 (10)0.0010 (10)0.0046 (9)
C30.0667 (17)0.0526 (14)0.0643 (17)0.0067 (12)0.0043 (13)0.0026 (12)
C40.0731 (18)0.0632 (15)0.0666 (17)0.0116 (12)0.0220 (14)0.0176 (12)
C50.100 (2)0.0681 (16)0.0423 (13)0.0282 (13)0.0172 (13)0.0013 (11)
C60.0832 (18)0.0457 (12)0.0405 (12)0.0136 (12)0.0018 (12)0.0054 (9)
C70.0482 (11)0.0377 (10)0.0378 (10)0.0006 (8)0.0085 (9)0.0055 (8)
C80.0470 (11)0.0349 (9)0.0367 (10)0.0014 (8)0.0108 (8)0.0048 (7)
C90.0435 (10)0.0352 (9)0.0349 (9)0.0020 (8)0.0096 (8)0.0046 (7)
C100.0501 (12)0.0476 (12)0.0379 (10)0.0016 (9)0.0074 (9)0.0051 (9)
C110.0588 (14)0.0557 (13)0.0393 (11)0.0059 (11)0.0081 (10)0.0143 (10)
C120.0738 (17)0.0448 (12)0.0515 (13)0.0005 (11)0.0141 (12)0.0183 (10)
C130.0666 (15)0.0386 (11)0.0517 (13)0.0078 (10)0.0130 (11)0.0074 (9)
C140.0467 (11)0.0357 (10)0.0373 (10)0.0005 (8)0.0099 (8)0.0045 (8)
C150.0730 (15)0.0533 (14)0.0440 (12)0.0058 (11)0.0002 (9)0.0152 (10)
C160.0666 (18)0.097 (2)0.0486 (15)0.0153 (16)0.0053 (13)0.0143 (15)
C170.0561 (13)0.0395 (11)0.0464 (12)0.0060 (9)0.0160 (10)0.0033 (9)
C180.0631 (16)0.0593 (16)0.096 (2)0.0238 (13)0.0233 (16)0.0205 (15)
C190.065 (2)0.128 (3)0.105 (3)0.030 (2)0.0010 (19)0.048 (3)
Geometric parameters (Å, º) top
Br1—C151.914 (3)C7—C151.484 (3)
Br1A—C151.9152 (10)C8—C91.439 (3)
S1—O21.417 (2)C8—C171.472 (3)
S1—O11.419 (2)C9—C141.389 (3)
S1—N11.6862 (19)C9—C101.405 (3)
S1—C11.751 (2)C10—C111.379 (3)
O3—C111.370 (3)C10—H100.9300
O3—C161.407 (4)C11—C121.390 (4)
O4—C171.320 (3)C12—C131.362 (4)
O4—C181.448 (3)C12—H120.9300
O5—C171.208 (3)C13—C141.398 (3)
N1—C71.405 (3)C13—H130.9300
N1—C141.417 (3)C15—H15A0.9700
C1—C61.372 (3)C15—H15B0.9700
C1—C21.381 (3)C15—H15C0.9700
C2—C31.371 (4)C15—H15D0.9700
C2—H20.9300C16—H16A0.9600
C3—C41.369 (4)C16—H16B0.9600
C3—H30.9300C16—H16C0.9600
C4—C51.365 (5)C18—C191.487 (5)
C4—H40.9300C18—H18A0.9700
C5—C61.388 (4)C18—H18B0.9700
C5—H50.9300C19—H19A0.9600
C6—H60.9300C19—H19B0.9600
C7—C81.364 (3)C19—H19C0.9600
O2—S1—O1120.09 (13)C11—C12—H12119.1
O2—S1—N1106.72 (11)C12—C13—C14117.7 (2)
O1—S1—N1105.29 (11)C12—C13—H13121.1
O2—S1—C1109.30 (12)C14—C13—H13121.1
O1—S1—C1108.93 (11)C9—C14—C13121.2 (2)
N1—S1—C1105.49 (10)C9—C14—N1107.98 (17)
C11—O3—C16117.9 (2)C13—C14—N1130.8 (2)
C17—O4—C18117.3 (2)C7—C15—Br1114.7 (2)
C7—N1—C14107.77 (17)C7—C15—Br1A103.7 (4)
C7—N1—S1127.88 (15)C7—C15—H15A108.6
C14—N1—S1124.15 (15)Br1—C15—H15A108.6
C6—C1—C2121.7 (2)Br1A—C15—H15A111.8
C6—C1—S1119.67 (19)C7—C15—H15B108.6
C2—C1—S1118.53 (18)Br1—C15—H15B108.6
C3—C2—C1118.6 (2)Br1A—C15—H15B116.3
C3—C2—H2120.7H15A—C15—H15B107.6
C1—C2—H2120.7C7—C15—H15C111.1
C4—C3—C2120.6 (3)Br1—C15—H15C107.3
C4—C3—H3119.7Br1A—C15—H15C111.0
C2—C3—H3119.7H15B—C15—H15C106.2
C5—C4—C3120.4 (3)C7—C15—H15D111.1
C5—C4—H4119.8Br1—C15—H15D102.7
C3—C4—H4119.8Br1A—C15—H15D110.4
C4—C5—C6120.3 (3)H15A—C15—H15D111.1
C4—C5—H5119.8H15C—C15—H15D109.5
C6—C5—H5119.8O3—C16—H16A109.5
C1—C6—C5118.4 (3)O3—C16—H16B109.5
C1—C6—H6120.8H16A—C16—H16B109.5
C5—C6—H6120.8O3—C16—H16C109.5
C8—C7—N1108.66 (18)H16A—C16—H16C109.5
C8—C7—C15127.3 (2)H16B—C16—H16C109.5
N1—C7—C15124.1 (2)O5—C17—O4123.3 (2)
C7—C8—C9108.47 (18)O5—C17—C8124.7 (2)
C7—C8—C17124.5 (2)O4—C17—C8112.02 (19)
C9—C8—C17127.0 (2)O4—C18—C19107.3 (3)
C14—C9—C10120.41 (19)O4—C18—H18A110.3
C14—C9—C8107.12 (18)C19—C18—H18A110.3
C10—C9—C8132.5 (2)O4—C18—H18B110.3
C11—C10—C9117.5 (2)C19—C18—H18B110.3
C11—C10—H10121.2H18A—C18—H18B108.5
C9—C10—H10121.2C18—C19—H19A109.5
O3—C11—C10123.9 (2)C18—C19—H19B109.5
O3—C11—C12114.8 (2)H19A—C19—H19B109.5
C10—C11—C12121.3 (2)C18—C19—H19C109.5
C13—C12—C11121.8 (2)H19A—C19—H19C109.5
C13—C12—H12119.1H19B—C19—H19C109.5
O2—S1—N1—C730.0 (2)C17—C8—C9—C101.3 (4)
O1—S1—N1—C7158.62 (19)C14—C9—C10—C110.3 (3)
C1—S1—N1—C786.2 (2)C8—C9—C10—C11178.5 (2)
O2—S1—N1—C14155.94 (18)C16—O3—C11—C106.6 (4)
O1—S1—N1—C1427.3 (2)C16—O3—C11—C12174.3 (2)
C1—S1—N1—C1487.87 (18)C9—C10—C11—O3179.0 (2)
O2—S1—C1—C68.6 (2)C9—C10—C11—C120.0 (3)
O1—S1—C1—C6141.6 (2)O3—C11—C12—C13179.0 (2)
N1—S1—C1—C6105.8 (2)C10—C11—C12—C130.1 (4)
O2—S1—C1—C2168.24 (19)C11—C12—C13—C140.1 (4)
O1—S1—C1—C235.3 (2)C10—C9—C14—C130.5 (3)
N1—S1—C1—C277.3 (2)C8—C9—C14—C13179.1 (2)
C6—C1—C2—C31.4 (4)C10—C9—C14—N1178.12 (19)
S1—C1—C2—C3178.2 (2)C8—C9—C14—N10.5 (2)
C1—C2—C3—C40.1 (4)C12—C13—C14—C90.4 (3)
C2—C3—C4—C50.9 (5)C12—C13—C14—N1177.8 (2)
C3—C4—C5—C60.2 (5)C7—N1—C14—C90.6 (2)
C2—C1—C6—C52.1 (4)S1—N1—C14—C9175.69 (14)
S1—C1—C6—C5178.8 (2)C7—N1—C14—C13179.0 (2)
C4—C5—C6—C11.2 (4)S1—N1—C14—C135.9 (3)
C14—N1—C7—C80.4 (2)C8—C7—C15—Br190.2 (3)
S1—N1—C7—C8175.24 (15)N1—C7—C15—Br190.1 (2)
C14—N1—C7—C15179.9 (2)C8—C7—C15—Br1A87.5 (3)
S1—N1—C7—C155.0 (3)N1—C7—C15—Br1A92.8 (3)
N1—C7—C8—C90.0 (2)C18—O4—C17—O52.9 (4)
C15—C7—C8—C9179.8 (2)C18—O4—C17—C8177.4 (2)
N1—C7—C8—C17179.39 (19)C7—C8—C17—O52.7 (4)
C15—C7—C8—C170.4 (4)C9—C8—C17—O5176.6 (2)
C7—C8—C9—C140.3 (2)C7—C8—C17—O4176.9 (2)
C17—C8—C9—C14179.7 (2)C9—C8—C17—O43.8 (3)
C7—C8—C9—C10178.1 (2)C17—O4—C18—C19171.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.932.563.472 (3)165
C2—H2···O5ii0.932.603.235 (3)126
C6—H6···O20.932.542.908 (4)104
C10—H10···O40.932.372.892 (3)116
C13—H13···O10.932.282.863 (3)120
C15—H15A···O50.972.312.911 (4)119
C15—H15D···O20.972.162.895 (4)131
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC19H18BrNO5S
Mr452.31
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)8.9988 (3), 9.2343 (2), 11.6068 (3)
α, β, γ (°)82.524 (1), 87.666 (2), 84.942 (3)
V3)952.16 (5)
Z2
Radiation typeMo Kα
µ (mm1)2.30
Crystal size (mm)0.20 × 0.20 × 0.16
Data collection
DiffractometerBruker Kappa APEXII
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.593, 0.692
No. of measured, independent and
observed [I > 2σ(I)] reflections
25160, 6169, 4163
Rint0.027
(sin θ/λ)max1)0.730
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.127, 1.04
No. of reflections6169
No. of parameters254
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.68, 0.89

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.932.563.472 (3)165
C2—H2···O5ii0.932.603.235 (3)126
C6—H6···O20.932.542.908 (4)104
C10—H10···O40.932.372.892 (3)116
C13—H13···O10.932.282.863 (3)120
C15—H15A···O50.972.312.911 (4)119
C15—H15D···O20.972.162.895 (4)131
Symmetry codes: (i) x+1, y+1, z+2; (ii) x, y+1, z.
 

Acknowledgements

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

References

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First citationChakkaravarthi, G., Dhayalan, V., Mohanakrishnan, A. K. & Manivannan, V. (2008). Acta Cryst. E64, o542.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationChakkaravarthi, G., Ramesh, N., Mohanakrishnan, A. K. & Manivannan, V. (2007). Acta Cryst. E63, o3564.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationYang, L. M., Lin, S. J., Hsu, F. L. & Yang, T. H. (2002). Bioorg. Med. Chem. Lett. 12, 1013–1015.  Web of Science CrossRef PubMed CAS Google Scholar

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