In the title molecule, C
17H
14BrNO
4S, 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
CCDC reference: 628045
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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-1
H-indole-3-carboxylate
top
Crystal data top
C17H14BrNO4S | F(000) = 824 |
Mr = 408.26 | Dx = 1.627 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6688 reflections |
a = 10.2224 (1) Å | θ = 2.2–26.8° |
b = 8.5086 (1) Å | µ = 2.61 mm−1 |
c = 19.1733 (3) Å | T = 293 K |
β = 91.445 (1)° | Block, colourless |
V = 1667.13 (4) Å3 | 0.54 × 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 tube | 3364 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.0°, θmin = 2.1° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −11→11 |
Tmin = 0.418, Tmax = 0.648 | l = −25→26 |
24996 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-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 parameters | Δρmax = 0.76 e Å−3 |
0 restraints | Δρmin = −1.09 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.43367 (3) | 0.78735 (5) | 0.216437 (15) | 0.06933 (13) | |
S1 | 0.77971 (6) | 0.96597 (7) | 0.12722 (3) | 0.04220 (15) | |
O1 | 0.71352 (18) | 1.0338 (2) | 0.18415 (10) | 0.0604 (5) | |
O2 | 0.86962 (18) | 1.0560 (2) | 0.08847 (12) | 0.0594 (5) | |
O3 | 0.25951 (19) | 0.7708 (3) | 0.06201 (11) | 0.0633 (5) | |
O4 | 0.32183 (18) | 0.6407 (2) | −0.03219 (11) | 0.0576 (5) | |
N1 | 0.66307 (17) | 0.9055 (2) | 0.06938 (9) | 0.0355 (4) | |
C1 | 0.5303 (2) | 0.8728 (3) | 0.08205 (11) | 0.0344 (5) | |
C2 | 0.4811 (2) | 0.7838 (3) | 0.02826 (12) | 0.0360 (5) | |
C3 | 0.5841 (2) | 0.7555 (3) | −0.02068 (12) | 0.0373 (5) | |
C4 | 0.5902 (3) | 0.6749 (3) | −0.08410 (13) | 0.0484 (6) | |
H4 | 0.5178 | 0.6212 | −0.1022 | 0.058* | |
C5 | 0.7069 (3) | 0.6773 (4) | −0.11911 (14) | 0.0581 (7) | |
H5 | 0.7127 | 0.6242 | −0.1613 | 0.070* | |
C6 | 0.8153 (3) | 0.7572 (4) | −0.09268 (15) | 0.0562 (7) | |
H6 | 0.8917 | 0.7576 | −0.1180 | 0.067* | |
C7 | 0.8133 (2) | 0.8359 (3) | −0.03018 (14) | 0.0473 (6) | |
H7 | 0.8866 | 0.8886 | −0.0124 | 0.057* | |
C8 | 0.6954 (2) | 0.8330 (3) | 0.00557 (12) | 0.0366 (5) | |
C9 | 0.8574 (2) | 0.7929 (3) | 0.15563 (11) | 0.0372 (5) | |
C10 | 0.7934 (3) | 0.6924 (4) | 0.19928 (14) | 0.0539 (7) | |
H10 | 0.7075 | 0.7123 | 0.2115 | 0.065* | |
C11 | 0.8585 (3) | 0.5614 (4) | 0.22483 (16) | 0.0653 (9) | |
H11 | 0.8160 | 0.4919 | 0.2541 | 0.078* | |
C12 | 0.9861 (3) | 0.5334 (4) | 0.20708 (14) | 0.0583 (7) | |
H12 | 1.0296 | 0.4452 | 0.2245 | 0.070* | |
C13 | 1.0491 (3) | 0.6346 (4) | 0.16417 (15) | 0.0559 (7) | |
H13 | 1.1354 | 0.6149 | 0.1527 | 0.067* | |
C14 | 0.9861 (2) | 0.7657 (3) | 0.13754 (14) | 0.0455 (6) | |
H14 | 1.0290 | 0.8344 | 0.1081 | 0.055* | |
C15 | 0.4569 (2) | 0.9399 (3) | 0.14088 (12) | 0.0420 (5) | |
H15A | 0.3717 | 0.9749 | 0.1238 | 0.050* | |
H15B | 0.5036 | 1.0308 | 0.1592 | 0.050* | |
C16 | 0.3430 (2) | 0.7333 (3) | 0.02245 (13) | 0.0429 (5) | |
C17 | 0.1896 (3) | 0.5808 (4) | −0.04044 (19) | 0.0713 (9) | |
H17A | 0.1827 | 0.5188 | −0.0822 | 0.107* | |
H17B | 0.1294 | 0.6672 | −0.0437 | 0.107* | |
H17C | 0.1693 | 0.5168 | −0.0009 | 0.107* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.05770 (18) | 0.1020 (3) | 0.04903 (17) | 0.01706 (17) | 0.01530 (12) | 0.02794 (16) |
S1 | 0.0376 (3) | 0.0382 (3) | 0.0505 (3) | 0.0024 (2) | −0.0049 (2) | −0.0074 (3) |
O1 | 0.0537 (10) | 0.0635 (13) | 0.0636 (12) | 0.0124 (9) | −0.0090 (9) | −0.0303 (10) |
O2 | 0.0470 (10) | 0.0427 (11) | 0.0882 (15) | −0.0084 (8) | −0.0039 (10) | 0.0069 (10) |
O3 | 0.0412 (10) | 0.0822 (15) | 0.0670 (13) | −0.0112 (10) | 0.0088 (9) | −0.0059 (11) |
O4 | 0.0512 (10) | 0.0579 (12) | 0.0631 (12) | −0.0076 (9) | −0.0109 (9) | −0.0081 (10) |
N1 | 0.0305 (8) | 0.0407 (11) | 0.0351 (9) | 0.0035 (8) | −0.0009 (7) | 0.0009 (8) |
C1 | 0.0325 (10) | 0.0359 (12) | 0.0350 (11) | 0.0054 (9) | 0.0016 (8) | 0.0058 (9) |
C2 | 0.0366 (10) | 0.0353 (12) | 0.0360 (11) | 0.0019 (9) | −0.0003 (8) | 0.0060 (9) |
C3 | 0.0420 (11) | 0.0355 (12) | 0.0344 (11) | 0.0061 (9) | 0.0003 (9) | 0.0046 (9) |
C4 | 0.0587 (15) | 0.0476 (15) | 0.0386 (13) | 0.0081 (12) | −0.0019 (11) | −0.0038 (11) |
C5 | 0.0729 (19) | 0.0627 (18) | 0.0389 (13) | 0.0235 (15) | 0.0072 (12) | −0.0041 (13) |
C6 | 0.0517 (15) | 0.0687 (19) | 0.0488 (15) | 0.0157 (14) | 0.0154 (12) | 0.0077 (14) |
C7 | 0.0398 (12) | 0.0544 (16) | 0.0482 (14) | 0.0087 (11) | 0.0074 (10) | 0.0070 (12) |
C8 | 0.0380 (11) | 0.0367 (12) | 0.0351 (11) | 0.0085 (9) | 0.0031 (8) | 0.0051 (9) |
C9 | 0.0325 (10) | 0.0447 (13) | 0.0342 (11) | 0.0039 (9) | −0.0038 (8) | −0.0037 (10) |
C10 | 0.0405 (13) | 0.0710 (19) | 0.0505 (15) | 0.0092 (12) | 0.0090 (11) | 0.0121 (14) |
C11 | 0.0586 (17) | 0.081 (2) | 0.0570 (17) | 0.0074 (15) | 0.0104 (13) | 0.0300 (16) |
C12 | 0.0552 (15) | 0.070 (2) | 0.0493 (15) | 0.0191 (14) | −0.0043 (12) | 0.0144 (14) |
C13 | 0.0391 (13) | 0.0694 (19) | 0.0593 (17) | 0.0149 (13) | 0.0017 (11) | 0.0069 (15) |
C14 | 0.0343 (11) | 0.0524 (15) | 0.0499 (14) | 0.0011 (10) | 0.0029 (10) | 0.0021 (12) |
C15 | 0.0399 (11) | 0.0470 (14) | 0.0392 (12) | 0.0078 (10) | 0.0032 (9) | 0.0034 (10) |
C16 | 0.0416 (12) | 0.0407 (13) | 0.0461 (13) | −0.0019 (10) | −0.0051 (10) | 0.0080 (11) |
C17 | 0.0598 (18) | 0.0607 (19) | 0.092 (2) | −0.0180 (15) | −0.0244 (17) | 0.0009 (18) |
Geometric parameters (Å, º) top
Br1—C15 | 1.964 (2) | C6—C7 | 1.373 (4) |
S1—O2 | 1.420 (2) | C6—H6 | 0.93 |
S1—O1 | 1.4211 (19) | C7—C8 | 1.401 (3) |
S1—N1 | 1.6881 (18) | C7—H7 | 0.93 |
S1—C9 | 1.753 (2) | C9—C10 | 1.373 (4) |
O3—C16 | 1.200 (3) | C9—C14 | 1.389 (3) |
O4—C16 | 1.325 (3) | C10—C11 | 1.381 (4) |
O4—C17 | 1.449 (3) | C10—H10 | 0.93 |
N1—C1 | 1.413 (3) | C11—C12 | 1.378 (4) |
N1—C8 | 1.417 (3) | C11—H11 | 0.93 |
C1—C2 | 1.365 (3) | C12—C13 | 1.363 (4) |
C1—C15 | 1.485 (3) | C12—H12 | 0.93 |
C2—C3 | 1.448 (3) | C13—C14 | 1.379 (4) |
C2—C16 | 1.477 (3) | C13—H13 | 0.93 |
C3—C8 | 1.398 (3) | C14—H14 | 0.93 |
C3—C4 | 1.399 (3) | C15—H15A | 0.97 |
C4—C5 | 1.383 (4) | C15—H15B | 0.97 |
C4—H4 | 0.93 | C17—H17A | 0.96 |
C5—C6 | 1.385 (4) | C17—H17B | 0.96 |
C5—H5 | 0.93 | C17—H17C | 0.96 |
| | | |
O2—S1—O1 | 120.64 (13) | C10—C9—C14 | 121.1 (2) |
O2—S1—N1 | 106.04 (11) | C10—C9—S1 | 119.58 (18) |
O1—S1—N1 | 106.64 (10) | C14—C9—S1 | 119.13 (19) |
O2—S1—C9 | 108.76 (11) | C9—C10—C11 | 119.1 (2) |
O1—S1—C9 | 108.85 (12) | C9—C10—H10 | 120.5 |
N1—S1—C9 | 104.75 (10) | C11—C10—H10 | 120.5 |
C16—O4—C17 | 115.4 (2) | C12—C11—C10 | 120.1 (3) |
C1—N1—C8 | 108.00 (18) | C12—C11—H11 | 119.9 |
C1—N1—S1 | 127.81 (15) | C10—C11—H11 | 119.9 |
C8—N1—S1 | 121.57 (14) | C13—C12—C11 | 120.3 (3) |
C2—C1—N1 | 108.45 (19) | C13—C12—H12 | 119.8 |
C2—C1—C15 | 127.2 (2) | C11—C12—H12 | 119.8 |
N1—C1—C15 | 124.1 (2) | C12—C13—C14 | 120.7 (2) |
C1—C2—C3 | 108.8 (2) | C12—C13—H13 | 119.6 |
C1—C2—C16 | 123.5 (2) | C14—C13—H13 | 119.6 |
C3—C2—C16 | 127.7 (2) | C13—C14—C9 | 118.6 (2) |
C8—C3—C4 | 119.4 (2) | C13—C14—H14 | 120.7 |
C8—C3—C2 | 106.7 (2) | C9—C14—H14 | 120.7 |
C4—C3—C2 | 133.9 (2) | C1—C15—Br1 | 112.27 (16) |
C5—C4—C3 | 118.2 (3) | C1—C15—H15A | 109.2 |
C5—C4—H4 | 120.9 | Br1—C15—H15A | 109.2 |
C3—C4—H4 | 120.9 | C1—C15—H15B | 109.2 |
C4—C5—C6 | 121.4 (3) | Br1—C15—H15B | 109.2 |
C4—C5—H5 | 119.3 | H15A—C15—H15B | 107.9 |
C6—C5—H5 | 119.3 | O3—C16—O4 | 123.6 (2) |
C7—C6—C5 | 121.9 (3) | O3—C16—C2 | 124.7 (2) |
C7—C6—H6 | 119.0 | O4—C16—C2 | 111.7 (2) |
C5—C6—H6 | 119.0 | O4—C17—H17A | 109.5 |
C6—C7—C8 | 116.7 (2) | O4—C17—H17B | 109.5 |
C6—C7—H7 | 121.6 | H17A—C17—H17B | 109.5 |
C8—C7—H7 | 121.6 | O4—C17—H17C | 109.5 |
C3—C8—C7 | 122.3 (2) | H17A—C17—H17C | 109.5 |
C3—C8—N1 | 108.08 (19) | H17B—C17—H17C | 109.5 |
C7—C8—N1 | 129.6 (2) | | |
| | | |
O2—S1—N1—C1 | −150.96 (19) | C6—C7—C8—N1 | −178.3 (2) |
O1—S1—N1—C1 | −21.2 (2) | C1—N1—C8—C3 | −0.4 (2) |
C9—S1—N1—C1 | 94.1 (2) | S1—N1—C8—C3 | 162.62 (16) |
O2—S1—N1—C8 | 49.7 (2) | C1—N1—C8—C7 | 177.6 (2) |
O1—S1—N1—C8 | 179.40 (18) | S1—N1—C8—C7 | −19.4 (3) |
C9—S1—N1—C8 | −65.29 (19) | O2—S1—C9—C10 | 174.6 (2) |
C8—N1—C1—C2 | −0.2 (2) | O1—S1—C9—C10 | 41.4 (2) |
S1—N1—C1—C2 | −161.79 (17) | N1—S1—C9—C10 | −72.4 (2) |
C8—N1—C1—C15 | −174.6 (2) | O2—S1—C9—C14 | −0.8 (2) |
S1—N1—C1—C15 | 23.8 (3) | O1—S1—C9—C14 | −134.0 (2) |
N1—C1—C2—C3 | 0.6 (3) | N1—S1—C9—C14 | 112.2 (2) |
C15—C1—C2—C3 | 174.8 (2) | C14—C9—C10—C11 | −0.7 (4) |
N1—C1—C2—C16 | −177.2 (2) | S1—C9—C10—C11 | −176.0 (2) |
C15—C1—C2—C16 | −3.0 (4) | C9—C10—C11—C12 | 0.6 (5) |
C1—C2—C3—C8 | −0.9 (3) | C10—C11—C12—C13 | −0.1 (5) |
C16—C2—C3—C8 | 176.9 (2) | C11—C12—C13—C14 | −0.4 (5) |
C1—C2—C3—C4 | −179.4 (3) | C12—C13—C14—C9 | 0.3 (4) |
C16—C2—C3—C4 | −1.7 (4) | C10—C9—C14—C13 | 0.2 (4) |
C8—C3—C4—C5 | −1.0 (4) | S1—C9—C14—C13 | 175.6 (2) |
C2—C3—C4—C5 | 177.4 (3) | C2—C1—C15—Br1 | 83.2 (3) |
C3—C4—C5—C6 | −0.1 (4) | N1—C1—C15—Br1 | −103.5 (2) |
C4—C5—C6—C7 | 1.0 (5) | C17—O4—C16—O3 | −2.2 (4) |
C5—C6—C7—C8 | −0.6 (4) | C17—O4—C16—C2 | 177.8 (2) |
C4—C3—C8—C7 | 1.4 (4) | C1—C2—C16—O3 | 3.6 (4) |
C2—C3—C8—C7 | −177.4 (2) | C3—C2—C16—O3 | −173.8 (3) |
C4—C3—C8—N1 | 179.5 (2) | C1—C2—C16—O4 | −176.3 (2) |
C2—C3—C8—N1 | 0.7 (2) | C3—C2—C16—O4 | 6.2 (3) |
C6—C7—C8—C3 | −0.6 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O4 | 0.93 | 2.45 | 2.956 (4) | 115 |
C7—H7···O2 | 0.93 | 2.41 | 2.991 (3) | 120 |
C10—H10···Br1 | 0.93 | 2.87 | 3.787 (3) | 167 |
C13—H13···O3i | 0.93 | 2.55 | 3.165 (4) | 124 |
C14—H14···O2 | 0.93 | 2.51 | 2.889 (3) | 104 |
C15—H15A···O3 | 0.97 | 2.38 | 2.877 (3) | 111 |
C15—H15B···O1 | 0.97 | 2.19 | 2.846 (3) | 124 |
C17—H17B···O2ii | 0.96 | 2.51 | 3.277 (4) | 137 |
C15—H15A···Cg1ii | 0.97 | 2.72 | 3.432 (3) | 131 |
C17—H17A···Cg3iii | 0.96 | 2.66 | 3.573 (4) | 160 |
C17—H17C···Cg1iii | 0.96 | 2.88 | 3.581 (4) | 131 |
Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+2, −z; (iii) −x+1, −y+1, −z. |