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In the title compound, C19H15Cl4NO3, the isoindole unit is planar and the oxazino ring adopts a twist-boat conformation. The dihedral angle between the isoindole unit and the phenyl ring is 50.46 (13)°. The mol­ecules are linked via inter­molecular O—H...O hydrogen bonds and weak C—H...O and C—H...Cl inter­actions, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015085/sj2273sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015085/sj2273Isup2.hkl
Contains datablock I

CCDC reference: 648206

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.052
  • wR factor = 0.159
  • Data-to-parameter ratio = 21.9

checkCIF/PLATON results

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Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 1.335 Test value = 1.275 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.91 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 1.34 e/A    PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.95 Ratio PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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).

7,8,9,10-Tetrachloro-10b-(2-hydroxy-1-phenylethyl)-3,4-dihydro-2H-1,3- oxazino[2,3-a]isoindol-6(10bH)-one top
Crystal data top
C19H15Cl4NO3Z = 2
Mr = 447.12F(000) = 456
Triclinic, P1Dx = 1.588 Mg m3
Hall symbol: -P 1Melting point = 472–474 K
a = 8.3221 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.7849 (2) ÅCell parameters from 5427 reflections
c = 14.9376 (4) Åθ = 1.4–30.0°
α = 100.189 (2)°µ = 0.65 mm1
β = 95.084 (2)°T = 100 K
γ = 117.496 (2)°Block, colorless
V = 935.12 (5) Å30.25 × 0.20 × 0.11 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
5427 independent reflections
Radiation source: fine-focus sealed tube3846 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 1.4°
ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 1212
Tmin = 0.852, Tmax = 0.931l = 2021
17582 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0811P)2 + 0.3933P]
where P = (Fo2 + 2Fc2)/3
5427 reflections(Δ/σ)max < 0.001
248 parametersΔρmax = 1.34 e Å3
0 restraintsΔρmin = 0.46 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.35648 (10)0.18187 (9)0.07477 (4)0.03045 (17)
Cl20.21402 (10)0.16250 (10)0.07990 (4)0.03195 (17)
Cl30.19629 (10)0.50016 (9)0.03362 (5)0.03362 (18)
Cl40.27527 (11)0.50780 (8)0.17335 (5)0.0375 (2)
O10.6228 (2)0.2911 (2)0.27910 (13)0.0257 (4)
O20.4555 (3)0.2231 (2)0.35900 (13)0.0269 (4)
O30.2698 (3)0.4254 (3)0.40012 (15)0.0336 (5)
N10.4965 (3)0.0512 (3)0.35060 (14)0.0215 (4)
C10.4411 (3)0.1236 (3)0.31553 (17)0.0219 (5)
C20.3667 (3)0.1630 (3)0.21445 (17)0.0208 (5)
C30.3024 (3)0.3172 (3)0.14597 (18)0.0218 (5)
C40.2623 (3)0.3144 (3)0.05455 (17)0.0236 (5)
C50.2744 (3)0.1613 (3)0.03292 (16)0.0226 (5)
C60.3365 (4)0.0066 (3)0.10301 (17)0.0231 (5)
C70.3856 (3)0.0081 (3)0.19366 (17)0.0193 (4)
C80.4600 (3)0.1389 (3)0.28327 (17)0.0208 (5)
C90.7889 (4)0.2851 (4)0.30798 (18)0.0283 (6)
H9A0.89420.38370.29530.034*
H9B0.78030.17600.27390.034*
C100.8139 (4)0.2952 (5)0.4102 (2)0.0426 (8)
H10A0.84170.41200.44430.051*
H10B0.91760.27770.42870.051*
C110.6409 (4)0.1558 (3)0.43456 (17)0.0263 (5)
H11A0.67070.07810.46250.032*
H11B0.59580.21330.47920.032*
C120.3154 (3)0.1993 (3)0.30467 (16)0.0187 (4)
H12A0.29970.25280.25460.022*
C130.1288 (3)0.0411 (3)0.29911 (18)0.0228 (5)
C140.0887 (4)0.0444 (4)0.3708 (2)0.0322 (6)
H14A0.17560.00050.42550.039*
C150.0793 (4)0.1959 (4)0.3616 (3)0.0428 (8)
H15A0.10390.25200.40990.051*
C160.2107 (4)0.2640 (4)0.2803 (3)0.0411 (7)
H16A0.32140.36790.27310.049*
C170.1755 (4)0.1767 (4)0.2110 (2)0.0357 (7)
H17A0.26460.21920.15740.043*
C180.0074 (4)0.0248 (3)0.22031 (19)0.0266 (5)
H18A0.01410.03360.17280.032*
C190.3823 (4)0.3440 (3)0.39507 (19)0.0280 (5)
H19A0.37930.29240.44760.034*
H19B0.50900.43270.39820.034*
H1O30.318 (7)0.516 (7)0.375 (3)0.087 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0504 (4)0.0291 (3)0.0246 (3)0.0271 (3)0.0125 (3)0.0115 (3)
Cl20.0425 (4)0.0406 (4)0.0173 (3)0.0256 (3)0.0039 (3)0.0034 (3)
Cl30.0392 (4)0.0258 (3)0.0292 (3)0.0162 (3)0.0020 (3)0.0075 (3)
Cl40.0572 (5)0.0170 (3)0.0370 (4)0.0206 (3)0.0030 (3)0.0018 (3)
O10.0253 (9)0.0148 (8)0.0327 (10)0.0063 (7)0.0071 (8)0.0046 (7)
O20.0357 (10)0.0225 (9)0.0271 (9)0.0173 (8)0.0056 (8)0.0084 (7)
O30.0407 (12)0.0231 (10)0.0375 (11)0.0175 (9)0.0119 (9)0.0010 (8)
N10.0245 (10)0.0176 (9)0.0202 (10)0.0097 (8)0.0004 (8)0.0034 (8)
C10.0224 (12)0.0206 (11)0.0227 (12)0.0114 (9)0.0033 (9)0.0038 (9)
C20.0241 (12)0.0156 (10)0.0222 (12)0.0100 (9)0.0035 (9)0.0032 (9)
C30.0227 (12)0.0143 (10)0.0274 (12)0.0097 (9)0.0017 (10)0.0022 (9)
C40.0262 (12)0.0200 (11)0.0228 (12)0.0132 (10)0.0019 (10)0.0030 (9)
C50.0264 (12)0.0253 (12)0.0166 (11)0.0146 (10)0.0027 (9)0.0009 (9)
C60.0299 (13)0.0224 (12)0.0231 (12)0.0166 (10)0.0088 (10)0.0070 (9)
C70.0201 (11)0.0167 (10)0.0213 (11)0.0097 (9)0.0034 (9)0.0034 (9)
C80.0238 (12)0.0136 (10)0.0212 (11)0.0069 (9)0.0025 (9)0.0028 (9)
C90.0254 (13)0.0278 (13)0.0253 (13)0.0092 (11)0.0059 (10)0.0021 (10)
C100.0315 (15)0.0476 (19)0.0241 (14)0.0025 (14)0.0013 (12)0.0030 (13)
C110.0318 (14)0.0247 (13)0.0174 (11)0.0117 (11)0.0007 (10)0.0018 (9)
C120.0263 (12)0.0153 (10)0.0164 (10)0.0119 (9)0.0044 (9)0.0032 (8)
C130.0264 (13)0.0190 (11)0.0254 (12)0.0137 (10)0.0042 (10)0.0041 (9)
C140.0310 (14)0.0324 (14)0.0348 (15)0.0149 (12)0.0048 (12)0.0147 (12)
C150.0404 (17)0.0386 (17)0.059 (2)0.0202 (14)0.0208 (16)0.0277 (16)
C160.0270 (15)0.0285 (15)0.065 (2)0.0114 (12)0.0113 (15)0.0084 (14)
C170.0266 (14)0.0310 (15)0.0444 (17)0.0160 (12)0.0013 (12)0.0061 (13)
C180.0284 (13)0.0257 (13)0.0276 (13)0.0176 (11)0.0010 (11)0.0007 (10)
C190.0351 (14)0.0230 (12)0.0266 (13)0.0169 (11)0.0049 (11)0.0000 (10)
Geometric parameters (Å, º) top
Cl1—C61.718 (2)C9—H9B0.9700
Cl2—C51.712 (2)C10—C111.526 (4)
Cl3—C41.727 (2)C10—H10A0.9700
Cl4—C31.712 (2)C10—H10B0.9700
O1—C81.414 (3)C11—H11A0.9700
O1—C91.438 (3)C11—H11B0.9700
O2—C11.219 (3)C12—C131.515 (3)
O3—C191.416 (3)C12—C191.535 (3)
O3—H1O30.88 (5)C12—H12A0.9800
N1—C11.365 (3)C13—C181.386 (4)
N1—C81.461 (3)C13—C141.393 (4)
N1—C111.472 (3)C14—C151.388 (4)
C1—C21.495 (3)C14—H14A0.9300
C2—C31.382 (3)C15—C161.389 (5)
C2—C71.390 (3)C15—H15A0.9300
C3—C41.384 (4)C16—C171.369 (5)
C4—C51.399 (3)C16—H16A0.9300
C5—C61.401 (3)C17—C181.390 (4)
C6—C71.383 (3)C17—H17A0.9300
C7—C81.532 (3)C18—H18A0.9300
C8—C121.559 (3)C19—H19A0.9700
C9—C101.503 (4)C19—H19B0.9700
C9—H9A0.9700
C8—O1—C9113.45 (19)C11—C10—H10A109.3
C19—O3—H1O3108 (3)C9—C10—H10B109.3
C1—N1—C8114.4 (2)C11—C10—H10B109.3
C1—N1—C11121.2 (2)H10A—C10—H10B108.0
C8—N1—C11120.26 (19)N1—C11—C10110.2 (2)
O2—C1—N1125.8 (2)N1—C11—H11A109.6
O2—C1—C2128.1 (2)C10—C11—H11A109.6
N1—C1—C2106.0 (2)N1—C11—H11B109.6
C3—C2—C7121.5 (2)C10—C11—H11B109.6
C3—C2—C1129.7 (2)H11A—C11—H11B108.1
C7—C2—C1108.6 (2)C13—C12—C19113.7 (2)
C2—C3—C4118.8 (2)C13—C12—C8110.68 (18)
C2—C3—Cl4120.74 (19)C19—C12—C8113.0 (2)
C4—C3—Cl4120.45 (19)C13—C12—H12A106.3
C3—C4—C5120.2 (2)C19—C12—H12A106.3
C3—C4—Cl3120.22 (19)C8—C12—H12A106.3
C5—C4—Cl3119.53 (19)C18—C13—C14117.9 (2)
C4—C5—C6120.4 (2)C18—C13—C12120.1 (2)
C4—C5—Cl2119.89 (18)C14—C13—C12122.0 (2)
C6—C5—Cl2119.73 (19)C15—C14—C13120.8 (3)
C7—C6—C5118.8 (2)C15—C14—H14A119.6
C7—C6—Cl1121.41 (19)C13—C14—H14A119.6
C5—C6—Cl1119.73 (19)C14—C15—C16120.2 (3)
C6—C7—C2120.1 (2)C14—C15—H15A119.9
C6—C7—C8130.6 (2)C16—C15—H15A119.9
C2—C7—C8109.3 (2)C17—C16—C15119.3 (3)
O1—C8—N1111.35 (19)C17—C16—H16A120.3
O1—C8—C7112.60 (19)C15—C16—H16A120.3
N1—C8—C7101.33 (18)C16—C17—C18120.4 (3)
O1—C8—C12107.01 (18)C16—C17—H17A119.8
N1—C8—C12113.50 (19)C18—C17—H17A119.8
C7—C8—C12111.14 (19)C13—C18—C17121.2 (3)
O1—C9—C10108.9 (2)C13—C18—H18A119.4
O1—C9—H9A109.9C17—C18—H18A119.4
C10—C9—H9A109.9O3—C19—C12110.9 (2)
O1—C9—H9B109.9O3—C19—H19A109.5
C10—C9—H9B109.9C12—C19—H19A109.5
H9A—C9—H9B108.3O3—C19—H19B109.5
C9—C10—C11111.4 (2)C12—C19—H19B109.5
C9—C10—H10A109.3H19A—C19—H19B108.0
C8—N1—C1—O2179.1 (2)C11—N1—C8—O132.4 (3)
C11—N1—C1—O223.6 (4)C1—N1—C8—C75.2 (3)
C8—N1—C1—C22.6 (3)C11—N1—C8—C7152.4 (2)
C11—N1—C1—C2154.7 (2)C1—N1—C8—C12114.1 (2)
O2—C1—C2—C32.2 (4)C11—N1—C8—C1288.4 (3)
N1—C1—C2—C3176.0 (2)C6—C7—C8—O156.2 (3)
O2—C1—C2—C7176.8 (2)C2—C7—C8—O1124.9 (2)
N1—C1—C2—C71.5 (3)C6—C7—C8—N1175.3 (2)
C7—C2—C3—C42.3 (4)C2—C7—C8—N15.9 (2)
C1—C2—C3—C4171.7 (2)C6—C7—C8—C1263.8 (3)
C7—C2—C3—Cl4178.55 (19)C2—C7—C8—C12115.0 (2)
C1—C2—C3—Cl47.5 (4)C8—O1—C9—C1067.8 (3)
C2—C3—C4—C54.5 (4)O1—C9—C10—C1152.5 (3)
Cl4—C3—C4—C5176.28 (19)C1—N1—C11—C10112.3 (3)
C2—C3—C4—Cl3175.71 (19)C8—N1—C11—C1043.7 (3)
Cl4—C3—C4—Cl33.5 (3)C9—C10—C11—N10.6 (4)
C3—C4—C5—C63.5 (4)O1—C8—C12—C13173.24 (19)
Cl3—C4—C5—C6176.80 (19)N1—C8—C12—C1363.5 (3)
C3—C4—C5—Cl2176.89 (19)C7—C8—C12—C1349.9 (2)
Cl3—C4—C5—Cl22.9 (3)O1—C8—C12—C1957.9 (2)
C4—C5—C6—C70.0 (4)N1—C8—C12—C1965.4 (3)
Cl2—C5—C6—C7179.64 (19)C7—C8—C12—C19178.79 (19)
C4—C5—C6—Cl1178.2 (2)C19—C12—C13—C18131.5 (2)
Cl2—C5—C6—Cl11.4 (3)C8—C12—C13—C18100.0 (3)
C5—C6—C7—C22.3 (4)C19—C12—C13—C1449.6 (3)
Cl1—C6—C7—C2179.54 (19)C8—C12—C13—C1478.9 (3)
C5—C6—C7—C8178.9 (2)C18—C13—C14—C153.0 (4)
Cl1—C6—C7—C80.8 (4)C12—C13—C14—C15175.9 (3)
C3—C2—C7—C61.2 (4)C13—C14—C15—C160.3 (5)
C1—C2—C7—C6176.3 (2)C14—C15—C16—C172.4 (5)
C3—C2—C7—C8179.8 (2)C15—C16—C17—C182.3 (4)
C1—C2—C7—C84.7 (3)C14—C13—C18—C173.1 (4)
C9—O1—C8—N124.7 (3)C12—C13—C18—C17175.8 (2)
C9—O1—C8—C788.3 (2)C16—C17—C18—C130.5 (4)
C9—O1—C8—C12149.27 (19)C13—C12—C19—O367.4 (3)
C1—N1—C8—O1125.1 (2)C8—C12—C19—O3165.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1O3···O2i0.88 (5)2.11 (6)2.955 (3)162 (4)
C11—H11A···O20.972.512.890 (3)103
C11—H11B···O2ii0.972.493.276 (3)139
C12—H12A···Cl10.982.783.465 (2)127
C12—H12A···Cl4i0.982.683.612 (3)158
C19—H19B···O10.972.492.900 (4)105
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z+1.
 

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