Crystal structure of rac-3-[2,3-bis­(phenyl­sulfan­yl)-3H-indol-3-yl]propanoic acid

In the crystal, the acid H atom is twisted roughly 180° from the typical carb­oxy conformation and mol­ecules are linked by pairs of O—H...N hydrogen bonds, involving the indole N atom, forming inversion dimers. Together with a weak C—H...O hydrogen bond, involving the carbonyl O atom, chains of inversion dimers are formed along [100].

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.092
• Data-to-parameter ratio = 17.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          8 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00100 Degree
PLAT793_ALERT_4_G The Model has Chirality at C4      (Centro SPGR)          R Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         51 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), enCIFer (Allen et al., 2004) and publCIF (Westrip, 2010).

rac-3-[2,3-Bis(phenylsulfanyl)-3H-indol-3-yl]propanoic acid

Crystal data

C23H19NO2S2	F(000) = 424
Mr = 405.51	Dx = 1.364 Mg m^−3
Triclinic, P1	Melting point: 444 K
a = 9.6498 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8610 (12) Å	Cell parameters from 2977 reflections
c = 10.8812 (13) Å	θ = 2.7–27.3°
α = 87.626 (1)°	µ = 0.29 mm^−1
β = 79.331 (1)°	T = 173 K
γ = 76.022 (1)°	Block, colourless
V = 987.4 (2) Å^3	0.23 × 0.12 × 0.10 mm
Z = 2

Data collection

Bruker APEXII CCD diffractometer	3396 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.032
φ and ω scans	θmax = 27.6°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
Tmin = 0.698, Tmax = 0.746	k = −12→12
11689 measured reflections	l = −14→14
4499 independent reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0362P)^2 + 0.1618P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
4499 reflections	Δρmax = 0.27 e Å^−3
254 parameters	Δρmin = −0.26 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.62197 (5)	0.45034 (5)	0.16673 (4)	0.03266 (13)
S2	0.92472 (5)	0.19331 (5)	0.20164 (4)	0.03283 (13)
O1	0.74866 (13)	0.71335 (13)	0.58120 (12)	0.0338 (3)
H1	0.6688	0.6928	0.6075	0.051*
O2	0.93299 (13)	0.65100 (13)	0.42699 (12)	0.0370 (3)
N1	0.54112 (14)	0.29215 (14)	0.36472 (13)	0.0251 (3)
C1	0.82262 (18)	0.62905 (17)	0.48697 (16)	0.0262 (4)
C2	0.76080 (18)	0.50855 (18)	0.46281 (16)	0.0289 (4)
H2A	0.6624	0.5453	0.4433	0.035*
H2B	0.7514	0.4515	0.5395	0.035*
C3	0.85486 (18)	0.41595 (17)	0.35510 (16)	0.0279 (4)
H3A	0.9532	0.3789	0.3747	0.033*
H3B	0.8644	0.4731	0.2784	0.033*
C4	0.79162 (17)	0.29341 (17)	0.33029 (15)	0.0258 (4)
C5	0.75579 (18)	0.20556 (17)	0.44228 (15)	0.0254 (4)
C6	0.84042 (19)	0.13254 (18)	0.52368 (17)	0.0310 (4)
H6	0.9401	0.1332	0.5147	0.037*
C7	0.7755 (2)	0.05780 (18)	0.61945 (17)	0.0350 (4)
H7	0.8320	0.0052	0.6757	0.042*
C8	0.6292 (2)	0.05935 (18)	0.63364 (17)	0.0350 (4)
H8	0.5872	0.0073	0.6994	0.042*
C9	0.54286 (19)	0.13564 (17)	0.55330 (16)	0.0295 (4)
H9	0.4424	0.1380	0.5637	0.035*
C10	0.60945 (18)	0.20787 (16)	0.45758 (15)	0.0251 (4)
C11	0.64132 (17)	0.34029 (17)	0.29370 (15)	0.0250 (4)
C12	0.43242 (19)	0.48511 (19)	0.16692 (15)	0.0295 (4)
C13	0.3474 (2)	0.6178 (2)	0.20041 (17)	0.0363 (4)
H13	0.3887	0.6865	0.2283	0.044*
C14	0.2017 (2)	0.6485 (2)	0.19258 (18)	0.0432 (5)
H14	0.1427	0.7391	0.2152	0.052*
C15	0.1417 (2)	0.5497 (2)	0.15248 (18)	0.0442 (5)
H15	0.0420	0.5726	0.1459	0.053*
C16	0.2255 (2)	0.4172 (2)	0.12167 (18)	0.0422 (5)
H16	0.1828	0.3482	0.0962	0.051*
C17	0.3717 (2)	0.3847 (2)	0.12777 (17)	0.0358 (4)
H17	0.4301	0.2939	0.1052	0.043*
C18	0.83442 (18)	0.06781 (19)	0.16376 (16)	0.0307 (4)
C19	0.7666 (2)	0.0890 (2)	0.06019 (18)	0.0444 (5)
H19	0.7669	0.1712	0.0115	0.053*
C20	0.6988 (3)	−0.0091 (3)	0.0277 (2)	0.0563 (6)
H20	0.6528	0.0057	−0.0433	0.068*
C21	0.6979 (2)	−0.1282 (2)	0.0980 (2)	0.0506 (6)
H21	0.6496	−0.1947	0.0764	0.061*
C22	0.7667 (2)	−0.1509 (2)	0.19934 (19)	0.0444 (5)
H22	0.7674	−0.2341	0.2467	0.053*
C23	0.8348 (2)	−0.05393 (19)	0.23299 (17)	0.0355 (4)
H23	0.8820	−0.0703	0.3034	0.043*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0282 (2)	0.0393 (3)	0.0309 (2)	−0.0096 (2)	−0.00598 (19)	0.0068 (2)
S2	0.0249 (2)	0.0364 (3)	0.0345 (3)	−0.00567 (19)	0.00119 (19)	−0.0076 (2)
O1	0.0281 (7)	0.0349 (7)	0.0405 (7)	−0.0121 (6)	−0.0035 (6)	−0.0088 (6)
O2	0.0303 (7)	0.0405 (8)	0.0426 (8)	−0.0175 (6)	0.0000 (6)	−0.0020 (6)
N1	0.0236 (7)	0.0249 (7)	0.0271 (7)	−0.0060 (6)	−0.0048 (6)	−0.0018 (6)
C1	0.0255 (9)	0.0273 (9)	0.0282 (9)	−0.0072 (7)	−0.0101 (7)	0.0035 (7)
C2	0.0246 (9)	0.0300 (9)	0.0326 (9)	−0.0104 (7)	−0.0011 (7)	−0.0025 (7)
C3	0.0223 (8)	0.0299 (9)	0.0325 (9)	−0.0089 (7)	−0.0038 (7)	−0.0017 (7)
C4	0.0208 (8)	0.0271 (9)	0.0279 (9)	−0.0035 (7)	−0.0027 (7)	−0.0034 (7)
C5	0.0262 (9)	0.0216 (8)	0.0274 (9)	−0.0041 (7)	−0.0033 (7)	−0.0047 (7)
C6	0.0290 (9)	0.0268 (9)	0.0361 (10)	−0.0031 (7)	−0.0075 (8)	−0.0026 (8)
C7	0.0397 (11)	0.0265 (9)	0.0368 (11)	0.0001 (8)	−0.0127 (8)	0.0012 (8)
C8	0.0449 (11)	0.0254 (9)	0.0337 (10)	−0.0089 (8)	−0.0050 (9)	0.0037 (8)
C9	0.0287 (9)	0.0239 (9)	0.0362 (10)	−0.0082 (7)	−0.0042 (8)	−0.0006 (7)
C10	0.0273 (9)	0.0212 (8)	0.0265 (9)	−0.0048 (7)	−0.0046 (7)	−0.0024 (7)
C11	0.0241 (8)	0.0231 (8)	0.0270 (9)	−0.0040 (7)	−0.0036 (7)	−0.0065 (7)
C12	0.0291 (9)	0.0360 (10)	0.0223 (9)	−0.0058 (8)	−0.0054 (7)	0.0048 (7)
C13	0.0371 (10)	0.0378 (11)	0.0320 (10)	−0.0065 (8)	−0.0043 (8)	0.0006 (8)
C14	0.0363 (11)	0.0459 (12)	0.0380 (11)	0.0020 (9)	0.0014 (9)	0.0029 (9)
C15	0.0280 (10)	0.0677 (15)	0.0333 (11)	−0.0099 (10)	−0.0007 (8)	0.0100 (10)
C16	0.0385 (11)	0.0565 (13)	0.0360 (11)	−0.0199 (10)	−0.0072 (9)	0.0033 (10)
C17	0.0376 (11)	0.0377 (11)	0.0327 (10)	−0.0090 (9)	−0.0075 (8)	0.0004 (8)
C18	0.0264 (9)	0.0330 (10)	0.0291 (9)	−0.0006 (7)	−0.0022 (7)	−0.0085 (8)
C19	0.0580 (14)	0.0411 (12)	0.0346 (11)	−0.0078 (10)	−0.0146 (10)	−0.0018 (9)
C20	0.0702 (16)	0.0599 (15)	0.0451 (13)	−0.0130 (12)	−0.0271 (12)	−0.0136 (11)
C21	0.0531 (14)	0.0479 (13)	0.0542 (14)	−0.0160 (11)	−0.0092 (11)	−0.0176 (11)
C22	0.0538 (13)	0.0347 (11)	0.0425 (12)	−0.0113 (10)	−0.0007 (10)	−0.0057 (9)
C23	0.0374 (10)	0.0328 (10)	0.0335 (10)	−0.0013 (8)	−0.0072 (8)	−0.0050 (8)

Geometric parameters (Å, º)

S1—C11	1.7305 (17)	C8—H8	0.9500
S1—C12	1.7773 (18)	C9—C10	1.385 (2)
S2—C18	1.7767 (18)	C9—H9	0.9500
S2—C4	1.8493 (16)	C12—C17	1.383 (2)
O1—C1	1.328 (2)	C12—C13	1.389 (3)
O1—H1	0.8400	C13—C14	1.382 (3)
O2—C1	1.2040 (19)	C13—H13	0.9500
N1—C11	1.293 (2)	C14—C15	1.370 (3)
N1—C10	1.435 (2)	C14—H14	0.9500
C1—C2	1.504 (2)	C15—C16	1.378 (3)
C2—C3	1.525 (2)	C15—H15	0.9500
C2—H2A	0.9900	C16—C17	1.382 (3)
C2—H2B	0.9900	C16—H16	0.9500
C3—C4	1.533 (2)	C17—H17	0.9500
C3—H3A	0.9900	C18—C19	1.389 (3)
C3—H3B	0.9900	C18—C23	1.390 (2)
C4—C5	1.502 (2)	C19—C20	1.382 (3)
C4—C11	1.533 (2)	C19—H19	0.9500
C5—C6	1.379 (2)	C20—C21	1.375 (3)
C5—C10	1.386 (2)	C20—H20	0.9500
C6—C7	1.392 (2)	C21—C22	1.374 (3)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.388 (3)	C22—C23	1.379 (3)
C7—H7	0.9500	C22—H22	0.9500
C8—C9	1.392 (2)	C23—H23	0.9500
C11—S1—C12	102.47 (8)	C9—C10—N1	126.35 (15)
C18—S2—C4	102.65 (8)	C5—C10—N1	111.96 (14)
C1—O1—H1	109.5	N1—C11—C4	114.43 (14)
C11—N1—C10	106.38 (14)	N1—C11—S1	127.16 (13)
O2—C1—O1	119.92 (15)	C4—C11—S1	118.40 (12)
O2—C1—C2	123.81 (16)	C17—C12—C13	120.40 (17)
O1—C1—C2	116.27 (14)	C17—C12—S1	120.78 (14)
C1—C2—C3	112.44 (13)	C13—C12—S1	118.72 (14)
C1—C2—H2A	109.1	C14—C13—C12	119.08 (19)
C3—C2—H2A	109.1	C14—C13—H13	120.5
C1—C2—H2B	109.1	C12—C13—H13	120.5
C3—C2—H2B	109.1	C15—C14—C13	120.61 (19)
H2A—C2—H2B	107.8	C15—C14—H14	119.7
C2—C3—C4	112.42 (13)	C13—C14—H14	119.7
C2—C3—H3A	109.1	C14—C15—C16	120.29 (19)
C4—C3—H3A	109.1	C14—C15—H15	119.9
C2—C3—H3B	109.1	C16—C15—H15	119.9
C4—C3—H3B	109.1	C15—C16—C17	119.99 (19)
H3A—C3—H3B	107.9	C15—C16—H16	120.0
C5—C4—C3	115.35 (14)	C17—C16—H16	120.0
C5—C4—C11	99.58 (13)	C16—C17—C12	119.61 (18)
C3—C4—C11	113.08 (13)	C16—C17—H17	120.2
C5—C4—S2	113.36 (11)	C12—C17—H17	120.2
C3—C4—S2	104.98 (11)	C19—C18—C23	119.20 (18)
C11—C4—S2	110.69 (11)	C19—C18—S2	119.45 (15)
C6—C5—C10	120.95 (16)	C23—C18—S2	121.31 (14)
C6—C5—C4	131.39 (15)	C20—C19—C18	120.20 (19)
C10—C5—C4	107.65 (14)	C20—C19—H19	119.9
C5—C6—C7	118.04 (17)	C18—C19—H19	119.9
C5—C6—H6	121.0	C21—C20—C19	120.1 (2)
C7—C6—H6	121.0	C21—C20—H20	119.9
C8—C7—C6	120.76 (17)	C19—C20—H20	119.9
C8—C7—H7	119.6	C22—C21—C20	119.9 (2)
C6—C7—H7	119.6	C22—C21—H21	120.0
C7—C8—C9	121.26 (17)	C20—C21—H21	120.0
C7—C8—H8	119.4	C21—C22—C23	120.6 (2)
C9—C8—H8	119.4	C21—C22—H22	119.7
C10—C9—C8	117.26 (16)	C23—C22—H22	119.7
C10—C9—H9	121.4	C22—C23—C18	119.89 (18)
C8—C9—H9	121.4	C22—C23—H23	120.1
C9—C10—C5	121.70 (16)	C18—C23—H23	120.1
O2—C1—C2—C3	0.9 (2)	C10—N1—C11—S1	−179.11 (12)
O1—C1—C2—C3	−178.65 (14)	C5—C4—C11—N1	−0.43 (18)
C1—C2—C3—C4	−179.85 (13)	C3—C4—C11—N1	−123.38 (16)
C2—C3—C4—C5	−52.58 (19)	S2—C4—C11—N1	119.15 (13)
C2—C3—C4—C11	61.13 (19)	C5—C4—C11—S1	178.90 (11)
C2—C3—C4—S2	−178.10 (12)	C3—C4—C11—S1	55.95 (17)
C18—S2—C4—C5	60.67 (13)	S2—C4—C11—S1	−61.52 (14)
C18—S2—C4—C3	−172.58 (11)	C12—S1—C11—N1	3.10 (17)
C18—S2—C4—C11	−50.24 (13)	C12—S1—C11—C4	−176.13 (12)
C3—C4—C5—C6	−57.2 (2)	C11—S1—C12—C17	−74.16 (15)
C11—C4—C5—C6	−178.58 (17)	C11—S1—C12—C13	109.44 (14)
S2—C4—C5—C6	63.8 (2)	C17—C12—C13—C14	−0.8 (3)
C3—C4—C5—C10	121.86 (15)	S1—C12—C13—C14	175.62 (14)
C11—C4—C5—C10	0.53 (16)	C12—C13—C14—C15	0.1 (3)
S2—C4—C5—C10	−117.07 (13)	C13—C14—C15—C16	1.3 (3)
C10—C5—C6—C7	1.9 (2)	C14—C15—C16—C17	−1.8 (3)
C4—C5—C6—C7	−179.11 (16)	C15—C16—C17—C12	1.1 (3)
C5—C6—C7—C8	−1.2 (3)	C13—C12—C17—C16	0.2 (3)
C6—C7—C8—C9	−0.2 (3)	S1—C12—C17—C16	−176.11 (14)
C7—C8—C9—C10	1.0 (3)	C4—S2—C18—C19	100.86 (16)
C8—C9—C10—C5	−0.4 (2)	C4—S2—C18—C23	−81.59 (15)
C8—C9—C10—N1	179.83 (15)	C23—C18—C19—C20	0.9 (3)
C6—C5—C10—C9	−1.1 (3)	S2—C18—C19—C20	178.48 (16)
C4—C5—C10—C9	179.70 (15)	C18—C19—C20—C21	0.2 (3)
C6—C5—C10—N1	178.71 (14)	C19—C20—C21—C22	−1.2 (3)
C4—C5—C10—N1	−0.51 (18)	C20—C21—C22—C23	1.2 (3)
C11—N1—C10—C9	−179.99 (16)	C21—C22—C23—C18	−0.2 (3)
C11—N1—C10—C5	0.23 (18)	C19—C18—C23—C22	−0.9 (3)
C10—N1—C11—C4	0.15 (18)	S2—C18—C23—C22	−178.43 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1^i	0.84	1.96	2.7622 (18)	159
C3—H3A···O2^ii	0.99	2.57	3.356 (2)	136

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1.