Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031509/ci2402sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031509/ci2402Isup2.hkl |
CCDC reference: 657672
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.047
- wR factor = 0.130
- Data-to-parameter ratio = 18.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O1 .. 2.98 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O2 .. C1 .. 2.98 Ang.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C8 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was synthesized by a photo-induced reaction between N-(2-hydroxyethyl)-4,5,6,7-tetrachlorophthalimide (0.025 M) and excess cycloheptariene in benzene (120 ml). The title compound was isolated using silica gel column chromatography with petroleum ether-ethyl acetate as eluent. Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of an ethanol solution.
The ratio of the refined occupancies for the major and minor components of the disordered hydroxyl O atoms, O3A and O3B, are 0.509 (5):0.491 (5). H atoms were positioned geometrically and refined using a riding model with O—H = 0.82 Å and C—H = 0.93–0.97 Å, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).
The construction of medium and large heterocyclic ring systems has constantly been an important task in organic synthesis (Evans & Holmes, 1991; Griesbeck et al., 1996; Illuminati & Mandolini, 1981). In continuation of our recent work on a new strategy for the synthesis of medium to large ring compounds based on photoinduced electron transfer (PET) reactions of N-(ω-hydroxyalkyl)-4,5,6,7- tetrachlorophthalimide (TCP) with electron rich alkenes, we studied the photoinduced reaction of N-(2-hydroxyethyl)-4,5,6,7- tetrachlorophthalimide (TCP) with cycloheptatriene and obtained the title compound. We report here the crystal structure of the title compound which is determined to show its steric structure (Xue et al., 2000).
Bond lengths and angles are in normal ranges (Allen et al., 1987) and are comparable to those in a related structure (Fun et al., 2007). The isoindole unit (C1—C8/N1) is essentially planar, with a maximum deviation of 0.066 (2) Å for atom C1. The seven-membered ring adopts a boat conformation.
Intramolecular C15—H15A···O2 interaction generates an S(5) ring motif (Fig. 1) (Bernstein et al., 1995). The crystal structure is stabilized by O—H···O and O—H···Cl (Fig. 2 and Table 1) interactions. These interactions link the molecules into a two-dimensional network parallel to the (0 1 0) plane. The relatively short distance [2.980 (2) Å] between atoms Cl1 and O1(-1 - x, -y, 2 - z) indicates the presence of intermolecular Cl···O interactions, which contribute to further stabilization of the crystal structure.
For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related literature, see: Evans & Holmes (1991); Griesbeck et al. (1996); Illuminati & Mandolini (1981); Xue et al. (2000); Fun et al. (2007).
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, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C17H13Cl4NO3 | F(000) = 856 |
Mr = 421.08 | Dx = 1.690 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9862 reflections |
a = 5.7285 (3) Å | θ = 1.5–28.8° |
b = 27.9820 (12) Å | µ = 0.73 mm−1 |
c = 10.7301 (5) Å | T = 100 K |
β = 105.816 (3)° | Needle, colourless |
V = 1654.86 (14) Å3 | 0.45 × 0.12 × 0.10 mm |
Z = 4 |
Bruker SMART APEXII CCD area-detector diffractometer | 4319 independent reflections |
Radiation source: fine-focus sealed tube | 3643 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.8°, θmin = 1.5° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −37→37 |
Tmin = 0.734, Tmax = 0.930 | l = −14→14 |
32385 measured reflections |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0699P)2 + 0.7172P] where P = (Fo2 + 2Fc2)/3 |
4319 reflections | (Δ/σ)max = 0.001 |
236 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
C17H13Cl4NO3 | V = 1654.86 (14) Å3 |
Mr = 421.08 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.7285 (3) Å | µ = 0.73 mm−1 |
b = 27.9820 (12) Å | T = 100 K |
c = 10.7301 (5) Å | 0.45 × 0.12 × 0.10 mm |
β = 105.816 (3)° |
Bruker SMART APEXII CCD area-detector diffractometer | 4319 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | 3643 reflections with I > 2σ(I) |
Tmin = 0.734, Tmax = 0.930 | Rint = 0.051 |
32385 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 1.12 | Δρmax = 0.51 e Å−3 |
4319 reflections | Δρmin = −0.60 e Å−3 |
236 parameters |
Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cl1 | −0.29215 (10) | 0.03836 (2) | 1.11550 (5) | 0.02248 (15) | |
Cl2 | 0.04401 (11) | 0.10146 (2) | 1.33363 (5) | 0.02604 (16) | |
Cl3 | 0.44031 (11) | 0.16567 (2) | 1.27276 (5) | 0.02525 (15) | |
Cl4 | 0.48531 (11) | 0.17301 (2) | 0.98860 (6) | 0.02581 (16) | |
O1 | −0.2907 (3) | 0.01311 (7) | 0.83031 (16) | 0.0304 (4) | |
O2 | 0.3526 (3) | 0.08766 (6) | 0.77716 (18) | 0.0269 (4) | |
H2A | 0.3809 | 0.0603 | 0.8045 | 0.040* | |
O3A | −0.4124 (7) | 0.04349 (13) | 0.4118 (3) | 0.0292 (10) | 0.509 (5) |
H3A | −0.3513 | 0.0577 | 0.3617 | 0.044* | 0.509 (5) |
O3B | −0.5578 (6) | 0.05223 (13) | 0.5737 (3) | 0.0245 (10) | 0.491 (5) |
H3B | −0.5516 | 0.0237 | 0.5919 | 0.037* | 0.491 (5) |
N1 | −0.0585 (3) | 0.06401 (6) | 0.74676 (17) | 0.0174 (4) | |
C1 | −0.1487 (4) | 0.04629 (8) | 0.8422 (2) | 0.0183 (4) | |
C2 | −0.0356 (4) | 0.07528 (8) | 0.9597 (2) | 0.0175 (4) | |
C3 | −0.0708 (4) | 0.07389 (8) | 1.0830 (2) | 0.0183 (4) | |
C4 | 0.0766 (4) | 0.10265 (8) | 1.1789 (2) | 0.0191 (4) | |
C5 | 0.2515 (4) | 0.13256 (8) | 1.1510 (2) | 0.0188 (4) | |
C6 | 0.2753 (4) | 0.13497 (8) | 1.0250 (2) | 0.0190 (4) | |
C7 | 0.1311 (4) | 0.10621 (7) | 0.9313 (2) | 0.0166 (4) | |
C8 | 0.1250 (4) | 0.10192 (8) | 0.7885 (2) | 0.0172 (4) | |
C9 | 0.0402 (4) | 0.14778 (8) | 0.7125 (2) | 0.0173 (4) | |
C10 | −0.1781 (4) | 0.16913 (8) | 0.7316 (2) | 0.0210 (5) | |
H10A | −0.2893 | 0.1488 | 0.7534 | 0.025* | |
C11 | −0.2327 (5) | 0.21585 (9) | 0.7204 (2) | 0.0250 (5) | |
H11A | −0.3834 | 0.2257 | 0.7280 | 0.030* | |
C12 | −0.0631 (5) | 0.25245 (8) | 0.6965 (2) | 0.0270 (5) | |
H12A | −0.1351 | 0.2839 | 0.6960 | 0.032* | |
H12B | 0.0857 | 0.2516 | 0.7664 | 0.032* | |
C13 | −0.0071 (6) | 0.24467 (9) | 0.5749 (3) | 0.0376 (7) | |
H13A | −0.0303 | 0.2702 | 0.5174 | 0.045* | |
C14 | 0.0752 (5) | 0.20388 (9) | 0.5379 (2) | 0.0312 (6) | |
H14A | 0.0825 | 0.2011 | 0.4526 | 0.037* | |
C15 | 0.1538 (4) | 0.16358 (8) | 0.6247 (2) | 0.0209 (5) | |
H15A | 0.2927 | 0.1474 | 0.6196 | 0.025* | |
C16 | −0.1193 (4) | 0.04355 (8) | 0.6172 (2) | 0.0206 (5) | |
H16A | −0.1414 | 0.0093 | 0.6232 | 0.025* | |
H16B | 0.0149 | 0.0487 | 0.5798 | 0.025* | |
C17 | −0.3483 (5) | 0.06508 (10) | 0.5283 (2) | 0.0273 (5) | |
H17A | −0.4799 | 0.0622 | 0.5687 | 0.033* | 0.509 (5) |
H17B | −0.3219 | 0.0988 | 0.5166 | 0.033* | 0.509 (5) |
H17C | −0.3703 | 0.0535 | 0.4417 | 0.033* | 0.491 (5) |
H17D | −0.3330 | 0.0992 | 0.5271 | 0.033* | 0.491 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0218 (3) | 0.0280 (3) | 0.0205 (3) | −0.0060 (2) | 0.0105 (2) | 0.00298 (19) |
Cl2 | 0.0296 (3) | 0.0344 (3) | 0.0164 (3) | −0.0046 (3) | 0.0102 (2) | 0.0011 (2) |
Cl3 | 0.0235 (3) | 0.0305 (3) | 0.0224 (3) | −0.0057 (2) | 0.0072 (2) | −0.0047 (2) |
Cl4 | 0.0251 (3) | 0.0285 (3) | 0.0286 (3) | −0.0099 (2) | 0.0152 (3) | −0.0029 (2) |
O1 | 0.0278 (10) | 0.0425 (10) | 0.0237 (8) | −0.0179 (8) | 0.0115 (8) | −0.0051 (7) |
O2 | 0.0189 (8) | 0.0211 (8) | 0.0478 (10) | 0.0030 (7) | 0.0215 (8) | 0.0033 (7) |
O3A | 0.032 (2) | 0.038 (2) | 0.0192 (16) | −0.0147 (16) | 0.0093 (15) | −0.0078 (13) |
O3B | 0.0146 (17) | 0.039 (2) | 0.0222 (17) | 0.0011 (15) | 0.0082 (14) | −0.0021 (14) |
N1 | 0.0166 (9) | 0.0211 (9) | 0.0170 (8) | 0.0003 (7) | 0.0090 (8) | 0.0002 (6) |
C1 | 0.0141 (10) | 0.0233 (10) | 0.0189 (10) | 0.0016 (9) | 0.0071 (9) | 0.0017 (8) |
C2 | 0.0141 (10) | 0.0218 (10) | 0.0179 (9) | 0.0020 (9) | 0.0065 (9) | 0.0038 (8) |
C3 | 0.0157 (11) | 0.0223 (10) | 0.0186 (10) | 0.0000 (9) | 0.0077 (9) | 0.0035 (8) |
C4 | 0.0181 (11) | 0.0233 (10) | 0.0183 (10) | 0.0029 (9) | 0.0087 (9) | 0.0032 (8) |
C5 | 0.0180 (11) | 0.0208 (10) | 0.0189 (10) | 0.0009 (9) | 0.0072 (9) | −0.0011 (8) |
C6 | 0.0167 (11) | 0.0196 (10) | 0.0233 (10) | −0.0004 (9) | 0.0099 (9) | 0.0022 (8) |
C7 | 0.0132 (10) | 0.0191 (10) | 0.0188 (10) | 0.0029 (8) | 0.0065 (9) | 0.0037 (7) |
C8 | 0.0162 (11) | 0.0207 (10) | 0.0185 (9) | 0.0024 (9) | 0.0111 (9) | 0.0009 (8) |
C9 | 0.0171 (11) | 0.0201 (10) | 0.0163 (9) | 0.0003 (9) | 0.0070 (9) | 0.0012 (8) |
C10 | 0.0194 (12) | 0.0252 (11) | 0.0196 (10) | 0.0022 (9) | 0.0074 (9) | 0.0024 (8) |
C11 | 0.0237 (12) | 0.0257 (11) | 0.0281 (12) | 0.0049 (10) | 0.0112 (10) | 0.0008 (9) |
C12 | 0.0316 (14) | 0.0210 (11) | 0.0314 (12) | 0.0031 (10) | 0.0139 (11) | 0.0019 (9) |
C13 | 0.056 (2) | 0.0247 (12) | 0.0430 (15) | 0.0027 (13) | 0.0313 (15) | 0.0060 (11) |
C14 | 0.0457 (17) | 0.0321 (13) | 0.0223 (11) | 0.0055 (12) | 0.0201 (12) | 0.0068 (10) |
C15 | 0.0226 (12) | 0.0233 (11) | 0.0206 (10) | 0.0023 (9) | 0.0125 (10) | 0.0010 (8) |
C16 | 0.0188 (11) | 0.0268 (11) | 0.0186 (10) | −0.0010 (9) | 0.0093 (9) | −0.0033 (8) |
C17 | 0.0204 (12) | 0.0454 (15) | 0.0192 (10) | 0.0022 (11) | 0.0106 (10) | −0.0003 (10) |
Cl1—C3 | 1.720 (2) | C8—C9 | 1.527 (3) |
Cl2—C4 | 1.721 (2) | C9—C15 | 1.357 (3) |
Cl3—C5 | 1.722 (2) | C9—C10 | 1.450 (3) |
Cl4—C6 | 1.728 (2) | C10—C11 | 1.342 (3) |
O1—C1 | 1.218 (3) | C10—H10A | 0.93 |
O2—C8 | 1.400 (3) | C11—C12 | 1.481 (4) |
O2—H2A | 0.82 | C11—H11A | 0.93 |
O3A—C17 | 1.346 (4) | C12—C13 | 1.443 (4) |
O3A—H3A | 0.82 | C12—H12A | 0.97 |
O3A—H17C | 0.4437 | C12—H12B | 0.97 |
O3B—C17 | 1.458 (4) | C13—C14 | 1.336 (4) |
O3B—H3B | 0.82 | C13—H13A | 0.93 |
N1—C1 | 1.360 (3) | C14—C15 | 1.453 (3) |
N1—C16 | 1.455 (3) | C14—H14A | 0.93 |
N1—C8 | 1.475 (3) | C15—H15A | 0.93 |
C1—C2 | 1.491 (3) | C16—C17 | 1.520 (3) |
C2—C7 | 1.383 (3) | C16—H16A | 0.97 |
C2—C3 | 1.392 (3) | C16—H16B | 0.97 |
C3—C4 | 1.395 (3) | C17—H17A | 0.97 |
C4—C5 | 1.399 (3) | C17—H17B | 0.97 |
C5—C6 | 1.398 (3) | C17—H17C | 0.96 |
C6—C7 | 1.374 (3) | C17—H17D | 0.96 |
C7—C8 | 1.527 (3) | ||
C8—O2—H2A | 109.5 | C10—C11—H11A | 118.6 |
C17—O3A—H3A | 109.5 | C12—C11—H11A | 118.6 |
H3A—O3A—H17C | 85.6 | C13—C12—C11 | 111.7 (2) |
C17—O3B—H3B | 109.5 | C13—C12—H12A | 109.3 |
C1—N1—C16 | 122.32 (19) | C11—C12—H12A | 109.3 |
C1—N1—C8 | 114.78 (18) | C13—C12—H12B | 109.3 |
C16—N1—C8 | 122.59 (18) | C11—C12—H12B | 109.3 |
O1—C1—N1 | 125.4 (2) | H12A—C12—H12B | 107.9 |
O1—C1—C2 | 128.9 (2) | C14—C13—C12 | 125.5 (2) |
N1—C1—C2 | 105.76 (19) | C14—C13—H13A | 117.2 |
C7—C2—C3 | 121.0 (2) | C12—C13—H13A | 117.2 |
C7—C2—C1 | 108.73 (18) | C13—C14—C15 | 123.0 (2) |
C3—C2—C1 | 130.3 (2) | C13—C14—H14A | 118.5 |
C2—C3—C4 | 118.0 (2) | C15—C14—H14A | 118.5 |
C2—C3—Cl1 | 120.99 (17) | C9—C15—C14 | 125.0 (2) |
C4—C3—Cl1 | 121.00 (16) | C9—C15—H15A | 117.5 |
C3—C4—C5 | 120.8 (2) | C14—C15—H15A | 117.5 |
C3—C4—Cl2 | 119.84 (17) | N1—C16—C17 | 112.61 (19) |
C5—C4—Cl2 | 119.36 (17) | N1—C16—H16A | 109.1 |
C6—C5—C4 | 120.0 (2) | C17—C16—H16A | 109.1 |
C6—C5—Cl3 | 120.09 (17) | N1—C16—H16B | 109.1 |
C4—C5—Cl3 | 119.88 (16) | C17—C16—H16B | 109.1 |
C7—C6—C5 | 118.8 (2) | H16A—C16—H16B | 107.8 |
C7—C6—Cl4 | 120.79 (17) | O3A—C17—O3B | 99.1 (3) |
C5—C6—Cl4 | 120.39 (17) | O3A—C17—C16 | 112.0 (3) |
C6—C7—C2 | 121.2 (2) | O3B—C17—C16 | 109.9 (2) |
C6—C7—C8 | 128.67 (19) | O3A—C17—H17A | 109.2 |
C2—C7—C8 | 110.09 (19) | C16—C17—H17A | 109.2 |
O2—C8—N1 | 111.84 (17) | O3A—C17—H17B | 109.2 |
O2—C8—C7 | 110.02 (18) | O3B—C17—H17B | 117.1 |
N1—C8—C7 | 100.43 (16) | C16—C17—H17B | 109.2 |
O2—C8—C9 | 111.15 (18) | H17A—C17—H17B | 107.9 |
N1—C8—C9 | 110.21 (18) | O3B—C17—H17C | 109.7 |
C7—C8—C9 | 112.76 (17) | C16—C17—H17C | 109.7 |
C15—C9—C10 | 124.0 (2) | H17A—C17—H17C | 119.4 |
C15—C9—C8 | 120.1 (2) | H17B—C17—H17C | 100.8 |
C10—C9—C8 | 115.55 (18) | O3A—C17—H17D | 115.9 |
C11—C10—C9 | 125.3 (2) | O3B—C17—H17D | 109.7 |
C11—C10—H10A | 117.4 | C16—C17—H17D | 109.7 |
C9—C10—H10A | 117.4 | H17A—C17—H17D | 100.1 |
C10—C11—C12 | 122.8 (2) | H17C—C17—H17D | 108.2 |
C16—N1—C1—O1 | −1.8 (4) | C1—N1—C8—O2 | 115.3 (2) |
C8—N1—C1—O1 | −175.5 (2) | C16—N1—C8—O2 | −58.4 (3) |
C16—N1—C1—C2 | 177.46 (19) | C1—N1—C8—C7 | −1.4 (2) |
C8—N1—C1—C2 | 3.8 (2) | C16—N1—C8—C7 | −175.08 (18) |
O1—C1—C2—C7 | 174.5 (2) | C1—N1—C8—C9 | −120.6 (2) |
N1—C1—C2—C7 | −4.8 (2) | C16—N1—C8—C9 | 65.8 (2) |
O1—C1—C2—C3 | −3.8 (4) | C6—C7—C8—O2 | 59.6 (3) |
N1—C1—C2—C3 | 177.0 (2) | C2—C7—C8—O2 | −119.8 (2) |
C7—C2—C3—C4 | −3.6 (3) | C6—C7—C8—N1 | 177.6 (2) |
C1—C2—C3—C4 | 174.5 (2) | C2—C7—C8—N1 | −1.8 (2) |
C7—C2—C3—Cl1 | 175.60 (17) | C6—C7—C8—C9 | −65.1 (3) |
C1—C2—C3—Cl1 | −6.3 (3) | C2—C7—C8—C9 | 115.5 (2) |
C2—C3—C4—C5 | 1.1 (3) | O2—C8—C9—C15 | 13.9 (3) |
Cl1—C3—C4—C5 | −178.07 (17) | N1—C8—C9—C15 | −110.7 (2) |
C2—C3—C4—Cl2 | −178.86 (17) | C7—C8—C9—C15 | 138.0 (2) |
Cl1—C3—C4—Cl2 | 2.0 (3) | O2—C8—C9—C10 | −172.13 (19) |
C3—C4—C5—C6 | 1.9 (3) | N1—C8—C9—C10 | 63.3 (2) |
Cl2—C4—C5—C6 | −178.11 (17) | C7—C8—C9—C10 | −48.0 (3) |
C3—C4—C5—Cl3 | −177.09 (17) | C15—C9—C10—C11 | −34.4 (4) |
Cl2—C4—C5—Cl3 | 2.9 (3) | C8—C9—C10—C11 | 151.9 (2) |
C4—C5—C6—C7 | −2.5 (3) | C9—C10—C11—C12 | −5.0 (4) |
Cl3—C5—C6—C7 | 176.50 (17) | C10—C11—C12—C13 | 61.7 (3) |
C4—C5—C6—Cl4 | 178.26 (17) | C11—C12—C13—C14 | −53.2 (4) |
Cl3—C5—C6—Cl4 | −2.7 (3) | C12—C13—C14—C15 | −9.5 (5) |
C5—C6—C7—C2 | 0.1 (3) | C10—C9—C15—C14 | 0.2 (4) |
Cl4—C6—C7—C2 | 179.29 (17) | C8—C9—C15—C14 | 173.6 (2) |
C5—C6—C7—C8 | −179.2 (2) | C13—C14—C15—C9 | 41.3 (4) |
Cl4—C6—C7—C8 | 0.0 (3) | C1—N1—C16—C17 | 87.9 (3) |
C3—C2—C7—C6 | 3.1 (3) | C8—N1—C16—C17 | −98.9 (2) |
C1—C2—C7—C6 | −175.4 (2) | N1—C16—C17—O3A | −175.5 (2) |
C3—C2—C7—C8 | −177.52 (19) | N1—C16—C17—O3B | −66.3 (3) |
C1—C2—C7—C8 | 4.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1i | 0.82 | 2.25 | 2.867 (3) | 132 |
O3A—H3A···Cl1ii | 0.82 | 2.81 | 3.435 (3) | 135 |
O3A—H3A···Cl2ii | 0.82 | 2.66 | 3.371 (4) | 146 |
C15—H15A···O2 | 0.93 | 2.34 | 2.733 (3) | 105 |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C17H13Cl4NO3 |
Mr | 421.08 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 100 |
a, b, c (Å) | 5.7285 (3), 27.9820 (12), 10.7301 (5) |
β (°) | 105.816 (3) |
V (Å3) | 1654.86 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.73 |
Crystal size (mm) | 0.45 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
Tmin, Tmax | 0.734, 0.930 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 32385, 4319, 3643 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.678 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.130, 1.12 |
No. of reflections | 4319 |
No. of parameters | 236 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.51, −0.60 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1i | 0.82 | 2.25 | 2.867 (3) | 132 |
O3A—H3A···Cl1ii | 0.82 | 2.81 | 3.435 (3) | 135 |
O3A—H3A···Cl2ii | 0.82 | 2.66 | 3.371 (4) | 146 |
C15—H15A···O2 | 0.93 | 2.34 | 2.733 (3) | 105 |
Symmetry codes: (i) x+1, y, z; (ii) x, y, z−1. |
The construction of medium and large heterocyclic ring systems has constantly been an important task in organic synthesis (Evans & Holmes, 1991; Griesbeck et al., 1996; Illuminati & Mandolini, 1981). In continuation of our recent work on a new strategy for the synthesis of medium to large ring compounds based on photoinduced electron transfer (PET) reactions of N-(ω-hydroxyalkyl)-4,5,6,7- tetrachlorophthalimide (TCP) with electron rich alkenes, we studied the photoinduced reaction of N-(2-hydroxyethyl)-4,5,6,7- tetrachlorophthalimide (TCP) with cycloheptatriene and obtained the title compound. We report here the crystal structure of the title compound which is determined to show its steric structure (Xue et al., 2000).
Bond lengths and angles are in normal ranges (Allen et al., 1987) and are comparable to those in a related structure (Fun et al., 2007). The isoindole unit (C1—C8/N1) is essentially planar, with a maximum deviation of 0.066 (2) Å for atom C1. The seven-membered ring adopts a boat conformation.
Intramolecular C15—H15A···O2 interaction generates an S(5) ring motif (Fig. 1) (Bernstein et al., 1995). The crystal structure is stabilized by O—H···O and O—H···Cl (Fig. 2 and Table 1) interactions. These interactions link the molecules into a two-dimensional network parallel to the (0 1 0) plane. The relatively short distance [2.980 (2) Å] between atoms Cl1 and O1(-1 - x, -y, 2 - z) indicates the presence of intermolecular Cl···O interactions, which contribute to further stabilization of the crystal structure.