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In the title mol­ecule, C17H14BrNO4S, the methoxy­carbonyl group is almost coplanar [dihedral angle = 5.89 (16)°] with the indole ring system, whereas the sulfonyl-bound phenyl ring is almost orthogonal to it [dihedral angle = 88.25 (6)°]. Weak C—H...O, C—H...π and π–π inter­actions link the mol­ecules into a sheet parallel to the ab plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043339/om2060sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043339/om2060Isup2.hkl
Contains datablock I

CCDC reference: 628045

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.040
  • wR factor = 0.105
  • Data-to-parameter ratio = 22.2

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.418 0.648 Tmin and Tmax expected: 0.281 0.625 RR = 1.438 Please check that your absorption correction is appropriate. PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.45 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.96 PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. O1 .. 3.27 Ang.
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 2 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).

Methyl 2-bromomethyl-1-phenylsulfonyl-1H-indole-3-carboxylate top
Crystal data top
C17H14BrNO4SF(000) = 824
Mr = 408.26Dx = 1.627 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6688 reflections
a = 10.2224 (1) Åθ = 2.2–26.8°
b = 8.5086 (1) ŵ = 2.61 mm1
c = 19.1733 (3) ÅT = 293 K
β = 91.445 (1)°Block, colourless
V = 1667.13 (4) Å30.54 × 0.42 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
4829 independent reflections
Radiation source: fine-focus sealed tube3364 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 2.1°
ω scansh = 1414
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1111
Tmin = 0.418, Tmax = 0.648l = 2526
24996 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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0416P)2 + 1.2297P]
where P = (Fo2 + 2Fc2)/3
4829 reflections(Δ/σ)max = 0.001
218 parametersΔρmax = 0.76 e Å3
0 restraintsΔρmin = 1.09 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
Br10.43367 (3)0.78735 (5)0.216437 (15)0.06933 (13)
S10.77971 (6)0.96597 (7)0.12722 (3)0.04220 (15)
O10.71352 (18)1.0338 (2)0.18415 (10)0.0604 (5)
O20.86962 (18)1.0560 (2)0.08847 (12)0.0594 (5)
O30.25951 (19)0.7708 (3)0.06201 (11)0.0633 (5)
O40.32183 (18)0.6407 (2)0.03219 (11)0.0576 (5)
N10.66307 (17)0.9055 (2)0.06938 (9)0.0355 (4)
C10.5303 (2)0.8728 (3)0.08205 (11)0.0344 (5)
C20.4811 (2)0.7838 (3)0.02826 (12)0.0360 (5)
C30.5841 (2)0.7555 (3)0.02068 (12)0.0373 (5)
C40.5902 (3)0.6749 (3)0.08410 (13)0.0484 (6)
H40.51780.62120.10220.058*
C50.7069 (3)0.6773 (4)0.11911 (14)0.0581 (7)
H50.71270.62420.16130.070*
C60.8153 (3)0.7572 (4)0.09268 (15)0.0562 (7)
H60.89170.75760.11800.067*
C70.8133 (2)0.8359 (3)0.03018 (14)0.0473 (6)
H70.88660.88860.01240.057*
C80.6954 (2)0.8330 (3)0.00557 (12)0.0366 (5)
C90.8574 (2)0.7929 (3)0.15563 (11)0.0372 (5)
C100.7934 (3)0.6924 (4)0.19928 (14)0.0539 (7)
H100.70750.71230.21150.065*
C110.8585 (3)0.5614 (4)0.22483 (16)0.0653 (9)
H110.81600.49190.25410.078*
C120.9861 (3)0.5334 (4)0.20708 (14)0.0583 (7)
H121.02960.44520.22450.070*
C131.0491 (3)0.6346 (4)0.16417 (15)0.0559 (7)
H131.13540.61490.15270.067*
C140.9861 (2)0.7657 (3)0.13754 (14)0.0455 (6)
H141.02900.83440.10810.055*
C150.4569 (2)0.9399 (3)0.14088 (12)0.0420 (5)
H15A0.37170.97490.12380.050*
H15B0.50361.03080.15920.050*
C160.3430 (2)0.7333 (3)0.02245 (13)0.0429 (5)
C170.1896 (3)0.5808 (4)0.04044 (19)0.0713 (9)
H17A0.18270.51880.08220.107*
H17B0.12940.66720.04370.107*
H17C0.16930.51680.00090.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.05770 (18)0.1020 (3)0.04903 (17)0.01706 (17)0.01530 (12)0.02794 (16)
S10.0376 (3)0.0382 (3)0.0505 (3)0.0024 (2)0.0049 (2)0.0074 (3)
O10.0537 (10)0.0635 (13)0.0636 (12)0.0124 (9)0.0090 (9)0.0303 (10)
O20.0470 (10)0.0427 (11)0.0882 (15)0.0084 (8)0.0039 (10)0.0069 (10)
O30.0412 (10)0.0822 (15)0.0670 (13)0.0112 (10)0.0088 (9)0.0059 (11)
O40.0512 (10)0.0579 (12)0.0631 (12)0.0076 (9)0.0109 (9)0.0081 (10)
N10.0305 (8)0.0407 (11)0.0351 (9)0.0035 (8)0.0009 (7)0.0009 (8)
C10.0325 (10)0.0359 (12)0.0350 (11)0.0054 (9)0.0016 (8)0.0058 (9)
C20.0366 (10)0.0353 (12)0.0360 (11)0.0019 (9)0.0003 (8)0.0060 (9)
C30.0420 (11)0.0355 (12)0.0344 (11)0.0061 (9)0.0003 (9)0.0046 (9)
C40.0587 (15)0.0476 (15)0.0386 (13)0.0081 (12)0.0019 (11)0.0038 (11)
C50.0729 (19)0.0627 (18)0.0389 (13)0.0235 (15)0.0072 (12)0.0041 (13)
C60.0517 (15)0.0687 (19)0.0488 (15)0.0157 (14)0.0154 (12)0.0077 (14)
C70.0398 (12)0.0544 (16)0.0482 (14)0.0087 (11)0.0074 (10)0.0070 (12)
C80.0380 (11)0.0367 (12)0.0351 (11)0.0085 (9)0.0031 (8)0.0051 (9)
C90.0325 (10)0.0447 (13)0.0342 (11)0.0039 (9)0.0038 (8)0.0037 (10)
C100.0405 (13)0.0710 (19)0.0505 (15)0.0092 (12)0.0090 (11)0.0121 (14)
C110.0586 (17)0.081 (2)0.0570 (17)0.0074 (15)0.0104 (13)0.0300 (16)
C120.0552 (15)0.070 (2)0.0493 (15)0.0191 (14)0.0043 (12)0.0144 (14)
C130.0391 (13)0.0694 (19)0.0593 (17)0.0149 (13)0.0017 (11)0.0069 (15)
C140.0343 (11)0.0524 (15)0.0499 (14)0.0011 (10)0.0029 (10)0.0021 (12)
C150.0399 (11)0.0470 (14)0.0392 (12)0.0078 (10)0.0032 (9)0.0034 (10)
C160.0416 (12)0.0407 (13)0.0461 (13)0.0019 (10)0.0051 (10)0.0080 (11)
C170.0598 (18)0.0607 (19)0.092 (2)0.0180 (15)0.0244 (17)0.0009 (18)
Geometric parameters (Å, º) top
Br1—C151.964 (2)C6—C71.373 (4)
S1—O21.420 (2)C6—H60.93
S1—O11.4211 (19)C7—C81.401 (3)
S1—N11.6881 (18)C7—H70.93
S1—C91.753 (2)C9—C101.373 (4)
O3—C161.200 (3)C9—C141.389 (3)
O4—C161.325 (3)C10—C111.381 (4)
O4—C171.449 (3)C10—H100.93
N1—C11.413 (3)C11—C121.378 (4)
N1—C81.417 (3)C11—H110.93
C1—C21.365 (3)C12—C131.363 (4)
C1—C151.485 (3)C12—H120.93
C2—C31.448 (3)C13—C141.379 (4)
C2—C161.477 (3)C13—H130.93
C3—C81.398 (3)C14—H140.93
C3—C41.399 (3)C15—H15A0.97
C4—C51.383 (4)C15—H15B0.97
C4—H40.93C17—H17A0.96
C5—C61.385 (4)C17—H17B0.96
C5—H50.93C17—H17C0.96
O2—S1—O1120.64 (13)C10—C9—C14121.1 (2)
O2—S1—N1106.04 (11)C10—C9—S1119.58 (18)
O1—S1—N1106.64 (10)C14—C9—S1119.13 (19)
O2—S1—C9108.76 (11)C9—C10—C11119.1 (2)
O1—S1—C9108.85 (12)C9—C10—H10120.5
N1—S1—C9104.75 (10)C11—C10—H10120.5
C16—O4—C17115.4 (2)C12—C11—C10120.1 (3)
C1—N1—C8108.00 (18)C12—C11—H11119.9
C1—N1—S1127.81 (15)C10—C11—H11119.9
C8—N1—S1121.57 (14)C13—C12—C11120.3 (3)
C2—C1—N1108.45 (19)C13—C12—H12119.8
C2—C1—C15127.2 (2)C11—C12—H12119.8
N1—C1—C15124.1 (2)C12—C13—C14120.7 (2)
C1—C2—C3108.8 (2)C12—C13—H13119.6
C1—C2—C16123.5 (2)C14—C13—H13119.6
C3—C2—C16127.7 (2)C13—C14—C9118.6 (2)
C8—C3—C4119.4 (2)C13—C14—H14120.7
C8—C3—C2106.7 (2)C9—C14—H14120.7
C4—C3—C2133.9 (2)C1—C15—Br1112.27 (16)
C5—C4—C3118.2 (3)C1—C15—H15A109.2
C5—C4—H4120.9Br1—C15—H15A109.2
C3—C4—H4120.9C1—C15—H15B109.2
C4—C5—C6121.4 (3)Br1—C15—H15B109.2
C4—C5—H5119.3H15A—C15—H15B107.9
C6—C5—H5119.3O3—C16—O4123.6 (2)
C7—C6—C5121.9 (3)O3—C16—C2124.7 (2)
C7—C6—H6119.0O4—C16—C2111.7 (2)
C5—C6—H6119.0O4—C17—H17A109.5
C6—C7—C8116.7 (2)O4—C17—H17B109.5
C6—C7—H7121.6H17A—C17—H17B109.5
C8—C7—H7121.6O4—C17—H17C109.5
C3—C8—C7122.3 (2)H17A—C17—H17C109.5
C3—C8—N1108.08 (19)H17B—C17—H17C109.5
C7—C8—N1129.6 (2)
O2—S1—N1—C1150.96 (19)C6—C7—C8—N1178.3 (2)
O1—S1—N1—C121.2 (2)C1—N1—C8—C30.4 (2)
C9—S1—N1—C194.1 (2)S1—N1—C8—C3162.62 (16)
O2—S1—N1—C849.7 (2)C1—N1—C8—C7177.6 (2)
O1—S1—N1—C8179.40 (18)S1—N1—C8—C719.4 (3)
C9—S1—N1—C865.29 (19)O2—S1—C9—C10174.6 (2)
C8—N1—C1—C20.2 (2)O1—S1—C9—C1041.4 (2)
S1—N1—C1—C2161.79 (17)N1—S1—C9—C1072.4 (2)
C8—N1—C1—C15174.6 (2)O2—S1—C9—C140.8 (2)
S1—N1—C1—C1523.8 (3)O1—S1—C9—C14134.0 (2)
N1—C1—C2—C30.6 (3)N1—S1—C9—C14112.2 (2)
C15—C1—C2—C3174.8 (2)C14—C9—C10—C110.7 (4)
N1—C1—C2—C16177.2 (2)S1—C9—C10—C11176.0 (2)
C15—C1—C2—C163.0 (4)C9—C10—C11—C120.6 (5)
C1—C2—C3—C80.9 (3)C10—C11—C12—C130.1 (5)
C16—C2—C3—C8176.9 (2)C11—C12—C13—C140.4 (5)
C1—C2—C3—C4179.4 (3)C12—C13—C14—C90.3 (4)
C16—C2—C3—C41.7 (4)C10—C9—C14—C130.2 (4)
C8—C3—C4—C51.0 (4)S1—C9—C14—C13175.6 (2)
C2—C3—C4—C5177.4 (3)C2—C1—C15—Br183.2 (3)
C3—C4—C5—C60.1 (4)N1—C1—C15—Br1103.5 (2)
C4—C5—C6—C71.0 (5)C17—O4—C16—O32.2 (4)
C5—C6—C7—C80.6 (4)C17—O4—C16—C2177.8 (2)
C4—C3—C8—C71.4 (4)C1—C2—C16—O33.6 (4)
C2—C3—C8—C7177.4 (2)C3—C2—C16—O3173.8 (3)
C4—C3—C8—N1179.5 (2)C1—C2—C16—O4176.3 (2)
C2—C3—C8—N10.7 (2)C3—C2—C16—O46.2 (3)
C6—C7—C8—C30.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O40.932.452.956 (4)115
C7—H7···O20.932.412.991 (3)120
C10—H10···Br10.932.873.787 (3)167
C13—H13···O3i0.932.553.165 (4)124
C14—H14···O20.932.512.889 (3)104
C15—H15A···O30.972.382.877 (3)111
C15—H15B···O10.972.192.846 (3)124
C17—H17B···O2ii0.962.513.277 (4)137
C15—H15A···Cg1ii0.972.723.432 (3)131
C17—H17A···Cg3iii0.962.663.573 (4)160
C17—H17C···Cg1iii0.962.883.581 (4)131
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+2, z; (iii) x+1, y+1, z.
 

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