(3R*,1′S*,3′R*)-3-(3′-Hydr­oxy-1′H,3′H-benzo[c]furan-1′-yl)-2-(2′′-hydroxy­ethyl)-2,3-dihydro-1H-benzo[c]pyrrol-1-one

The title compound, C₁₈H₁₇NO₄, is the first example of a mol­ecular structure where the isobenzofuran and isoindoline groups are directly bonded. In the crystal structure, mol­ecules are linked by O—H...O hydrogen bonds into sheets parallel to (001). Weaker inter­actions are also present, with C—H...O and π–π stacking inter­actions between the substituted furan and substituted pyrrole aromatic rings [centroid-to-centroid distance 3.3172 (13) Å].

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.069
• Data-to-parameter ratio = 8.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.99 Ratio
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8

Alert level G
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           26.02
           From the CIF: _reflns_number_total               1737
           Count of symmetry unique reflns         1738
           Completeness (_total/calc)             99.94%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1'    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3'    = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

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

   3 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
   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

---

S1. Comment

Our research project deals with chemical and electrochemical properties of diketones (Zuman, 2004). As a part of this study, we have observed that a main product of the reaction of orthophthalaldehyde with amines in low concentrations about 10 ^-3 mol/l is reducible about 0.5 V more negatively than the parent dialdehyde. In order to study this reaction as well as in order to identify the product (isoindoline derivative is expected to be formed) the reaction of phthalaldehyde with kolamine (2-aminoethanol) was performed.

In ethanol, however, the reaction results in a mixture of non-separable, viscous, probably polymeric compounds. On the other hand, the reaction in acetonitrile leads to two minor products together with formation of a non-separable mixture. The minor products were isolated, purified, crystallized and analyzed by NMR and single-crystal X-ray diffraction.

One of these compounds was identified as 2-(2''-hydroxyethyl)-3-(3'-hydroxy-1'H,3'H-benzo[c]furan-1'-yl-1H,3H- benzo[c]pyrrol-1-one (here reported as a title structure) while the second compound was characterized as 2-(2-hydroxyethyl)-1H,3H benzo[c]pyrrol-1-one (Urban et al., 2007) as described in the preceeding article.

For more details, see Urban et al. (2007).

Two kinds of the O—H···O hydrogen bonds bind the title molecules into layers parallel to (001). The graph set motifs are C₁¹(9) and C₁¹(10) for the O1···O3 and O4···O3 hydrogen bonds, respectively.

The atoms in the five-membered ring N2–C1–C7a–C4a–C3 (substituted pyrrole) form a fair plane with a maximal deviation of C4a from the mean plane that is 0.010 (2) Å. On the other hand, the atoms in the five-membered ring O2'–C3'–C4'a–C7'a–C1' (substituted furan) are situated approximately in the plane with a maximal deviation from the mean plane for C3' that is 0.082 (3) Å.

The dihedral angle between the pyrrole and the attached phenyl ring is 1.19 (8)° while the dihedral angle between the substituted furan and the attached phenyl ring is 6.97 (8)°. These values also indicate a lesser aromaticity of the isobenzofuran ring in comparison with the isoindoline ring.

There is also a short π–π electron interaction between the aromatic rings O2'–C3'–C4'a–C7'a–C1' and N2–C1–C7a–C4a–C3 as indicates the distance between the respective centroids being 3.3172 (13) Å.

Many isoindoline derivatives display biological as well as pharmaceutical activity (Mukherjee et al., 2000).

Related literature

For the structure of a closely related compound isolated from the same reaction, see: Urban et al. (2007). For related literature, see: Becker & Coppens (1974); Zuman (2004). For an article on the biological activity of isoindolines, see: Mukherjee et al. (2000).

S2. Experimental

The reaction has been described in the preceeding paper (Urban et al., 2007). At least two products were produced by the reaction. Column chromatography afforded 256 mg of the title compound (I), 150 mg after its recrystallization from CHCl₃:n–C₆H₁₄.

S3. Refinement

In the absence of significant anomalous scattering effects 1249 Friedel pairs have been merged (R_int = 0.022). All of the H atoms could be discerned in the difference Fourier maps, nevertheless, all of the H attached to the C atoms were constrained in a riding motion approximation while the hydroxyl H atoms were restrained (0.820 (1) Å) and their isotropic displacement parameters were freely refined, C_aryl—H = 0.93, C_methylene—H = 0.97, C_methine—H = 0.98 Å while U_isoH = 1.2U_eqC. The absolute configuration has not been determined.

Computing details

Data collection: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997); data reduction: COLLECT (Nonius, 1998) and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: JANA2000 (Petříček et al., 2000); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: JANA2000 (Petříček et al., 2000).

Figures

	Fig. 1. The molecules of the title structure (I) with displacement parameters shown at 50% probability level.
	Fig. 2. A view of the title structure (I) with O—H···O hydrogen bonds.

(3R*,1'S*,3'R*)-3-(3'-Hydroxy-1'H,3'H- benzo[c]furan-1'-yl)-2-(2''-hydroxyethyl)-2,3-dihydro-1H- benzo[c]pyrrol-1-one

Crystal data

C18H17NO4	F(000) = 656
Mr = 311.3	Dx = 1.363 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1756 reflections
a = 7.0292 (1) Å	θ = 1–26.0°
b = 11.9861 (5) Å	µ = 0.10 mm^−1
c = 18.0014 (7) Å	T = 150 K
V = 1516.67 (9) Å^3	Prism, colourless
Z = 4	0.2 × 0.08 × 0.05 mm

Data collection

Nonius KappaCCD area-detector diffractometer	1482 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
Graphite monochromator	θmax = 26.0°, θmin = 2.0°
Detector resolution: 9.091 pixels mm^-1	h = −8→8
φ and ω scans	k = −14→14
18223 measured reflections	l = −22→22
1737 independent reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F > 3σ(F)] = 0.037	Weighting scheme based on measured s.u.'s w = 1/(σ^2(I) + 0.0004I^2)
wR(F) = 0.069	(Δ/σ)max = 0.006
S = 1.65	Δρmax = 0.16 e Å^−3
1737 reflections	Δρmin = −0.17 e Å^−3
217 parameters	Extinction correction: B-C type 1 Lorentzian isotropic (Becker & Coppens, 1974)
2 restraints	Extinction coefficient: 1.57 (16)
60 constraints

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

	x	y	z	Uiso*/Ueq
C1	0.6319 (3)	0.35574 (19)	0.31944 (13)	0.0247 (7)
O1	0.4921 (2)	0.36611 (15)	0.36055 (9)	0.0344 (6)
N2	0.7803 (2)	0.28509 (16)	0.33170 (10)	0.0228 (6)
C3	0.9250 (3)	0.28969 (18)	0.27316 (12)	0.0223 (7)
H3	1.049523	0.313389	0.291876	0.0268*
C4a	0.8429 (3)	0.37409 (19)	0.22012 (12)	0.0229 (7)
C7a	0.6721 (3)	0.41363 (19)	0.24872 (13)	0.0243 (7)
C4	0.9105 (3)	0.41434 (19)	0.15273 (12)	0.0254 (8)
H4	1.025186	0.389264	0.133152	0.0305*
C5	0.8021 (3)	0.49305 (18)	0.11539 (13)	0.0286 (8)
H5	0.843911	0.519653	0.069689	0.0344*
C6	0.6330 (3)	0.5332 (2)	0.14428 (13)	0.0304 (8)
H6	0.564561	0.58684	0.118234	0.0364*
C7	0.5651 (3)	0.49403 (19)	0.21169 (13)	0.0300 (8)
H7	0.451645	0.520785	0.231403	0.036*
O2'	0.8001 (2)	0.13188 (13)	0.20416 (8)	0.0284 (5)
C3'	0.8425 (3)	0.09010 (18)	0.13168 (13)	0.0256 (7)
H3'	0.742632	0.110399	0.096186	0.0307*
C4'a	1.0382 (3)	0.13391 (19)	0.11551 (12)	0.0221 (7)
C7'a	1.1135 (3)	0.18025 (19)	0.17942 (13)	0.0222 (7)
C1'	0.9675 (3)	0.17481 (19)	0.23995 (12)	0.0239 (7)
H1'	1.008275	0.125368	0.280284	0.0286*
C4'	1.1405 (3)	0.13336 (19)	0.04959 (13)	0.0297 (8)
H4'	1.091314	0.100496	0.006917	0.0356*
C5'	1.3188 (3)	0.18345 (19)	0.04942 (14)	0.0322 (8)
H5'	1.388937	0.18607	0.005654	0.0387*
C6'	1.3937 (3)	0.2297 (2)	0.11368 (14)	0.0310 (8)
H6'	1.513096	0.262987	0.112345	0.0372*
C7'	1.2934 (3)	0.22706 (19)	0.17991 (14)	0.0271 (8)
H7'	1.345299	0.255859	0.223395	0.0325*
O3	0.8433 (2)	−0.02678 (14)	0.13010 (10)	0.0316 (6)
H3O	0.737 (2)	−0.055 (3)	0.131 (2)	0.107 (14)*
C1''	0.7943 (3)	0.21383 (19)	0.39678 (12)	0.0254 (7)
H1''a	0.675818	0.216763	0.424362	0.0304*
H1''b	0.807196	0.136731	0.381209	0.0304*
C2''	0.9573 (3)	0.24420 (19)	0.44749 (13)	0.0278 (8)
H2''a	0.963299	0.191412	0.488262	0.0334*
H2''b	1.076237	0.238248	0.420462	0.0334*
O4	0.9379 (3)	0.35389 (15)	0.47616 (10)	0.0349 (6)
H4O	0.993 (4)	0.395 (2)	0.4465 (14)	0.086 (14)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0259 (12)	0.0258 (14)	0.0224 (13)	−0.0003 (11)	0.0000 (11)	−0.0029 (11)
O1	0.0323 (9)	0.0402 (11)	0.0308 (10)	0.0089 (8)	0.0089 (8)	0.0042 (9)
N2	0.0266 (10)	0.0256 (11)	0.0162 (10)	0.0031 (8)	0.0011 (8)	0.0006 (9)
C3	0.0205 (11)	0.0269 (13)	0.0195 (13)	0.0011 (10)	0.0018 (9)	0.0005 (11)
C4a	0.0270 (11)	0.0219 (12)	0.0199 (12)	−0.0033 (10)	−0.0029 (10)	−0.0029 (11)
C7a	0.0284 (11)	0.0223 (12)	0.0222 (13)	−0.0014 (10)	−0.0027 (10)	−0.0026 (10)
C4	0.0291 (12)	0.0221 (13)	0.0249 (14)	−0.0007 (10)	0.0011 (10)	−0.0029 (11)
C5	0.0361 (14)	0.0242 (14)	0.0256 (14)	−0.0039 (11)	−0.0021 (11)	0.0011 (11)
C6	0.0363 (13)	0.0262 (14)	0.0286 (14)	0.0022 (11)	−0.0081 (11)	0.0025 (12)
C7	0.0305 (13)	0.0300 (14)	0.0295 (14)	0.0066 (12)	−0.0029 (11)	−0.0018 (12)
O2'	0.0248 (8)	0.0306 (9)	0.0298 (10)	−0.0061 (7)	0.0054 (7)	−0.0079 (8)
C3'	0.0273 (12)	0.0239 (13)	0.0254 (14)	0.0016 (10)	0.0045 (11)	−0.0027 (11)
C4'a	0.0227 (11)	0.0196 (12)	0.0241 (13)	0.0025 (10)	0.0008 (10)	0.0006 (11)
C7'a	0.0220 (11)	0.0210 (13)	0.0237 (13)	0.0045 (9)	0.0020 (10)	0.0023 (10)
C1'	0.0228 (11)	0.0266 (13)	0.0222 (13)	0.0004 (10)	−0.0006 (10)	−0.0005 (11)
C4'	0.0347 (13)	0.0268 (13)	0.0276 (14)	−0.0003 (11)	0.0019 (11)	−0.0014 (12)
C5'	0.0311 (12)	0.0331 (14)	0.0324 (15)	−0.0028 (12)	0.0122 (12)	−0.0018 (13)
C6'	0.0229 (11)	0.0315 (15)	0.0387 (16)	−0.0015 (10)	0.0053 (11)	−0.0001 (12)
C7'	0.0225 (11)	0.0291 (15)	0.0296 (15)	0.0002 (10)	−0.0011 (11)	−0.0019 (12)
O3	0.0296 (9)	0.0230 (10)	0.0422 (11)	−0.0031 (7)	0.0046 (8)	−0.0034 (8)
C1''	0.0302 (12)	0.0264 (14)	0.0195 (13)	0.0006 (10)	0.0033 (10)	0.0022 (11)
C2''	0.0356 (13)	0.0255 (13)	0.0224 (13)	−0.0007 (11)	−0.0002 (11)	0.0017 (11)
O4	0.0498 (10)	0.0271 (11)	0.0279 (11)	−0.0029 (9)	0.0007 (8)	−0.0038 (9)

Geometric parameters (Å, º)

C1—O1	1.237 (3)	C5'—C6'	1.387 (3)
C1—N2	1.362 (3)	C6'—C7'	1.385 (3)
C1—C7a	1.477 (3)	C1''—C2''	1.510 (3)
N2—C3	1.466 (3)	C2''—O4	1.419 (3)
N2—C1''	1.453 (3)	C3—H3	0.98
C3—C4a	1.506 (3)	C4—H4	0.93
C3—C1'	1.531 (3)	C5—H5	0.93
C4a—C7a	1.390 (3)	C6—H6	0.93
C4a—C4	1.389 (3)	C7—H7	0.93
C7a—C7	1.392 (3)	C3'—H3'	0.98
C4—C5	1.387 (3)	C1'—H1'	0.98
C5—C6	1.384 (3)	C4'—H4'	0.93
C6—C7	1.386 (3)	C5'—H5'	0.93
O2'—C3'	1.429 (3)	C6'—H6'	0.93
O2'—C1'	1.437 (3)	C7'—H7'	0.93
C3'—C4'a	1.501 (3)	O3—H3O	0.82 (2)
C3'—O3	1.401 (3)	C1''—H1''a	0.97
C4'a—C7'a	1.383 (3)	C1''—H1''b	0.97
C4'a—C4'	1.388 (3)	C2''—H2''a	0.97
C7'a—C1'	1.499 (3)	C2''—H2''b	0.97
C7'a—C7'	1.383 (3)	O4—H4O	0.82 (3)
C4'—C5'	1.389 (3)
O1—C1—N2	125.1 (2)	O2'—C3'—C4'a	104.22 (17)
O1—C1—C7a	128.4 (2)	O2'—C3'—O3	111.69 (18)
N2—C1—C7a	106.57 (18)	C4'a—C3'—O3	110.02 (18)
C1—N2—C3	113.06 (18)	C3'—C4'a—C7'a	109.29 (19)
C1—N2—C1''	123.23 (18)	C3'—C4'a—C4'	129.7 (2)
C3—N2—C1''	123.70 (17)	C7'a—C4'a—C4'	120.97 (19)
N2—C3—C4a	102.43 (16)	C4'a—C7'a—C1'	108.97 (17)
N2—C3—C1'	112.48 (17)	C4'a—C7'a—C7'	121.2 (2)
C4a—C3—C1'	115.56 (18)	C1'—C7'a—C7'	129.7 (2)
C3—C4a—C7a	108.98 (18)	C3—C1'—O2'	109.73 (16)
C3—C4a—C4	130.99 (19)	C3—C1'—C7'a	112.24 (18)
C7a—C4a—C4	120.0 (2)	O2'—C1'—C7'a	104.50 (17)
C1—C7a—C4a	108.93 (19)	C4'a—C4'—C5'	117.9 (2)
C1—C7a—C7	129.4 (2)	C4'—C5'—C6'	120.9 (2)
C4a—C7a—C7	121.7 (2)	C5'—C6'—C7'	121.1 (2)
C4a—C4—C5	118.2 (2)	C7'a—C7'—C6'	117.9 (2)
C4—C5—C6	121.8 (2)	N2—C1''—C2''	113.39 (18)
C5—C6—C7	120.5 (2)	C1''—C2''—O4	111.75 (19)
C7a—C7—C6	117.9 (2)	H1''a—C1''—H1''b	105.2
C3'—O2'—C1'	111.36 (15)	H2''a—C2''—H2''b	107.1