3-(2-Chloro-4-hydroxy­phen­yl)-1-thio­isocoumarin

The structure of the title compound, C₁₅H₉ClO₂S, has a thio­isocoumarin unit and a substituted phenyl group that are twisted at a dihedral angle of 33.40 (6)° with respect to one another. In addition to weak O—H...S inter­actions, C—H...S/O/Cl-type inter­actions that stabilize the structure are also observed.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.040
• wR factor = 0.107
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O2     -   H2     ...          ?

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT030_ALERT_1_C _diffrn_reflns_number .LE.  _reflns_number_total          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C13     ..       5.30 su
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2     ..  S1      ..       2.97 Ang.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C15 H9 Cl1 O2 S1
            Atom count from _chemical_formula_moiety:C15 H9 Cl1 O3 S1
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.40
           From the CIF: _reflns_number_total               2703
           Count of symmetry unique reflns         1640
           Completeness (_total/calc)            164.82%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1063
           Fraction of Friedel pairs measured     0.648
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

3-(2-Chloro-4-hydroxyphenyl)-1-thioisocoumarin

Crystal data

C15H9ClO3S	F(000) = 592
Mr = 288.73	Dx = 1.543 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2703 reflections
a = 7.177 (3) Å	θ = 3.6–27.4°
b = 10.662 (8) Å	µ = 0.47 mm^−1
c = 16.238 (12) Å	T = 173 K
V = 1242.6 (14) Å^3	Prism, yellow
Z = 4	0.08 × 0.06 × 0.05 mm

Data collection

Nonius KappaCCD area-detector diffractometer	2703 independent reflections
Radiation source: fine-focus sealed tube	2479 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ω and φ scans	θmax = 27.4°, θmin = 3.6°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −8→9
Tmin = 0.964, Tmax = 0.977	k = −13→13
2703 measured reflections	l = −20→20

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + (0.0557P)^2 + 0.6208P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.107	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.32 e Å^−3
2703 reflections	Δρmin = −0.35 e Å^−3
174 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.025 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with 1100 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.20 (8)

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

	x	y	z	Uiso*/Ueq
Cl1	0.72732 (10)	0.02314 (6)	0.06334 (4)	0.0374 (2)
S1	0.70531 (14)	0.61769 (7)	−0.09404 (5)	0.0508 (3)
O1	0.7709 (2)	0.39025 (15)	−0.05761 (10)	0.0299 (4)
O2	0.8846 (3)	−0.12579 (17)	−0.22038 (12)	0.0364 (4)
H2	0.9067	−0.1914	−0.1935	0.055*
C1	0.7648 (4)	0.5107 (2)	−0.02866 (15)	0.0305 (5)
C2	0.8106 (3)	0.5297 (2)	0.05762 (14)	0.0299 (5)
C3	0.8038 (4)	0.6507 (3)	0.09187 (18)	0.0374 (6)
H3	0.7731	0.7211	0.0576	0.045*
C4	0.8453 (4)	0.6662 (3)	0.17476 (18)	0.0421 (7)
H4	0.8410	0.7481	0.1993	0.051*
C5	0.8904 (4)	0.5661 (3)	0.22330 (18)	0.0419 (7)
H5	0.9182	0.5785	0.2806	0.050*
C6	0.8986 (4)	0.4465 (3)	0.19010 (16)	0.0359 (6)
H6	0.9281	0.3762	0.2246	0.043*
C7	0.8599 (3)	0.4261 (2)	0.10656 (15)	0.0293 (5)
C8	0.8714 (3)	0.3049 (2)	0.06912 (16)	0.0295 (5)
H8	0.9122	0.2335	0.1003	0.035*
C9	0.8307 (4)	0.2889 (2)	−0.01030 (15)	0.0267 (5)
C10	0.8458 (3)	0.1763 (2)	−0.06232 (16)	0.0277 (5)
C11	0.8066 (4)	0.0543 (2)	−0.03568 (15)	0.0294 (5)
C12	0.8207 (4)	−0.0478 (2)	−0.08822 (17)	0.0350 (6)
H12	0.7939	−0.1311	−0.0691	0.042*
C13	0.8749 (4)	−0.0264 (3)	−0.16802 (17)	0.0367 (6)
C14	0.9182 (4)	0.0902 (3)	−0.19808 (17)	0.0371 (6)
H14	0.9575	0.1001	−0.2542	0.045*
C15	0.9017 (4)	0.1920 (3)	−0.14453 (16)	0.0322 (5)
H15	0.9293	0.2745	−0.1649	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0461 (4)	0.0299 (3)	0.0362 (3)	−0.0003 (3)	0.0062 (3)	0.0056 (3)
S1	0.0789 (6)	0.0299 (3)	0.0437 (4)	0.0025 (4)	−0.0167 (4)	−0.0001 (3)
O1	0.0397 (9)	0.0213 (7)	0.0286 (8)	0.0002 (7)	−0.0039 (8)	−0.0009 (6)
O2	0.0491 (11)	0.0230 (9)	0.0371 (10)	0.0067 (8)	0.0015 (9)	−0.0152 (8)
C1	0.0343 (13)	0.0262 (11)	0.0310 (11)	−0.0010 (10)	0.0010 (10)	−0.0027 (9)
C2	0.0310 (12)	0.0292 (11)	0.0295 (11)	−0.0040 (10)	0.0005 (9)	−0.0027 (10)
C3	0.0406 (15)	0.0326 (13)	0.0390 (13)	−0.0054 (11)	0.0023 (12)	−0.0052 (11)
C4	0.0473 (17)	0.0374 (15)	0.0416 (15)	−0.0107 (12)	0.0061 (13)	−0.0157 (13)
C5	0.0438 (16)	0.0510 (17)	0.0310 (13)	−0.0122 (13)	0.0008 (12)	−0.0091 (12)
C6	0.0381 (14)	0.0402 (15)	0.0294 (13)	−0.0026 (12)	0.0000 (10)	−0.0014 (11)
C7	0.0260 (12)	0.0325 (12)	0.0296 (12)	−0.0028 (10)	0.0010 (9)	−0.0019 (10)
C8	0.0296 (13)	0.0280 (12)	0.0309 (12)	0.0033 (10)	0.0007 (10)	0.0018 (10)
C9	0.0275 (13)	0.0227 (11)	0.0299 (12)	−0.0004 (9)	0.0007 (9)	0.0015 (9)
C10	0.0243 (11)	0.0259 (11)	0.0329 (12)	0.0017 (9)	−0.0012 (10)	−0.0005 (10)
C11	0.0308 (13)	0.0256 (11)	0.0318 (11)	0.0025 (9)	0.0018 (10)	0.0032 (9)
C12	0.0363 (14)	0.0250 (12)	0.0437 (14)	0.0029 (10)	−0.0011 (11)	−0.0028 (11)
C13	0.0359 (14)	0.0338 (13)	0.0403 (14)	0.0047 (12)	−0.0016 (11)	−0.0143 (12)
C14	0.0370 (15)	0.0435 (16)	0.0309 (13)	0.0030 (12)	0.0030 (10)	−0.0064 (11)
C15	0.0330 (13)	0.0310 (13)	0.0326 (13)	−0.0003 (11)	0.0000 (11)	−0.0006 (11)

Geometric parameters (Å, º)

Cl1—C11	1.738 (3)	C6—C7	1.402 (4)
S1—C1	1.615 (3)	C6—H6	0.9600
O1—C1	1.369 (3)	C7—C8	1.431 (4)
O1—C9	1.394 (3)	C8—C9	1.333 (4)
O2—C13	1.361 (3)	C8—H8	0.9600
O2—H2	0.8400	C9—C10	1.472 (3)
C1—C2	1.453 (3)	C10—C11	1.399 (3)
C2—C7	1.406 (4)	C10—C15	1.404 (4)
C2—C3	1.406 (4)	C11—C12	1.387 (4)
C3—C4	1.388 (4)	C12—C13	1.372 (4)
C3—H3	0.9600	C12—H12	0.9600
C4—C5	1.366 (4)	C13—C14	1.371 (4)
C4—H4	0.9601	C14—C15	1.396 (4)
C5—C6	1.386 (4)	C14—H14	0.9599
C5—H5	0.9600	C15—H15	0.9600
C1—O1—C9	123.3 (2)	C9—C8—H8	118.4
C13—O2—H2	109.5	C7—C8—H8	120.6
O1—C1—C2	117.0 (2)	C8—C9—O1	120.1 (2)
O1—C1—S1	116.4 (2)	C8—C9—C10	130.0 (2)
C2—C1—S1	126.5 (2)	O1—C9—C10	109.8 (2)
C7—C2—C3	120.4 (2)	C11—C10—C15	117.5 (2)
C7—C2—C1	119.5 (2)	C11—C10—C9	124.5 (2)
C3—C2—C1	120.1 (2)	C15—C10—C9	118.0 (2)
C4—C3—C2	119.0 (3)	C12—C11—C10	121.7 (2)
C4—C3—H3	121.2	C12—C11—Cl1	116.3 (2)
C2—C3—H3	119.7	C10—C11—Cl1	121.99 (19)
C5—C4—C3	121.2 (3)	C13—C12—C11	118.1 (3)
C5—C4—H4	118.6	C13—C12—H12	121.0
C3—C4—H4	120.2	C11—C12—H12	120.9
C4—C5—C6	120.3 (3)	O2—C13—C14	118.2 (2)
C4—C5—H5	120.0	O2—C13—C12	118.4 (3)
C6—C5—H5	119.7	C14—C13—C12	123.5 (2)
C5—C6—C7	120.7 (3)	C13—C14—C15	117.6 (2)
C5—C6—H6	120.1	C13—C14—H14	120.3
C7—C6—H6	119.2	C15—C14—H14	122.1
C2—C7—C6	118.4 (2)	C14—C15—C10	121.6 (3)
C2—C7—C8	118.9 (2)	C14—C15—H15	118.7
C6—C7—C8	122.7 (2)	C10—C15—H15	119.7
C9—C8—C7	120.9 (2)
C9—O1—C1—C2	−4.6 (3)	C7—C8—C9—C10	175.0 (2)
C9—O1—C1—S1	175.90 (19)	C1—O1—C9—C8	5.4 (4)
O1—C1—C2—C7	0.6 (4)	C1—O1—C9—C10	−172.1 (2)
S1—C1—C2—C7	−180.0 (2)	C8—C9—C10—C11	37.6 (4)
O1—C1—C2—C3	−178.8 (2)	O1—C9—C10—C11	−145.3 (2)
S1—C1—C2—C3	0.6 (4)	C8—C9—C10—C15	−143.0 (3)
C7—C2—C3—C4	−0.4 (4)	O1—C9—C10—C15	34.1 (3)
C1—C2—C3—C4	179.0 (3)	C15—C10—C11—C12	−0.5 (4)
C2—C3—C4—C5	−0.7 (4)	C9—C10—C11—C12	178.9 (2)
C3—C4—C5—C6	1.0 (5)	C15—C10—C11—Cl1	−177.4 (2)
C4—C5—C6—C7	−0.3 (4)	C9—C10—C11—Cl1	2.0 (4)
C3—C2—C7—C6	1.1 (4)	C10—C11—C12—C13	0.1 (4)
C1—C2—C7—C6	−178.3 (2)	Cl1—C11—C12—C13	177.2 (2)
C3—C2—C7—C8	−178.0 (2)	C11—C12—C13—O2	−178.4 (2)
C1—C2—C7—C8	2.6 (4)	C11—C12—C13—C14	0.9 (4)
C5—C6—C7—C2	−0.8 (4)	O2—C13—C14—C15	177.9 (2)
C5—C6—C7—C8	178.3 (3)	C12—C13—C14—C15	−1.5 (4)
C2—C7—C8—C9	−2.0 (4)	C13—C14—C15—C10	1.1 (4)
C6—C7—C8—C9	178.9 (3)	C11—C10—C15—C14	−0.1 (4)
C7—C8—C9—O1	−1.8 (4)	C9—C10—C15—C14	−179.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···S1^i	0.84	2.97	3.653 (3)	140
C12—H12···S1^i	0.96	2.78	3.663 (4)	153
C15—H15···O2^ii	0.96	2.53	3.307 (3)	139
C3—H3···S1	0.96	2.74	3.120 (4)	104
C8—H8···Cl1	0.96	2.67	3.178 (3)	113

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