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The mol­ecules of the title compound, C21H20N2O3, are linked by O—H...O and C—H...N hydrogen bonds, and by π–π interactions. The cyclo­butane ring is puckered, with a dihedral angle of 11.55 (3)° between the two planes. The phenyl ring shows positional disorder.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803029246/dn6109sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803029246/dn6109Isup2.hkl
Contains datablock I

CCDC reference: 232180

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.054
  • wR factor = 0.134
  • Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.93
Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact C19B .. C20B = 3.03 Ang. PLAT432_ALERT_2_B Short Inter X...Y Contact C20B .. C20B = 2.90 Ang.
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 2824 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 3049 Completeness (_total/calc) 92.62% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.93 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT301_ALERT_3_C Main Residue Disorder ......................... 10.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C16 - C17 = 1.38 Ang. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.50 Deg. C21A -C16 -C21B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.10 Deg. C19A -C18 -C19B 1.555 1.555 1.555
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII for Windows (Farrugia, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2-[2-Hydroxyimino-2-(3-methyl-3-phenylcyclobutyl)ethyl]isoindole-1,3-dione top
Crystal data top
C21H20N2O3F(000) = 736
Mr = 348.39Dx = 1.336 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9229 reflections
a = 14.6497 (14) Åθ = 1.5–29.6°
b = 5.6976 (3) ŵ = 0.09 mm1
c = 21.965 (2) ÅT = 293 K
β = 109.095 (7)°Plate, colourless
V = 1732.5 (3) Å30.80 × 0.34 × 0.08 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
1590 reflections with I > 2σ(I)
Radiation source: sealed X-ray tubeRint = 0.071
Plane graphite monochromatorθmax = 25.0°, θmin = 1.5°
Detector resolution: 6.67 pixels mm-1h = 1716
φ scansk = 66
5446 measured reflectionsl = 1826
2824 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.134 w = 1/[σ2(Fo2) + (0.0555P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
2824 reflectionsΔρmax = 0.19 e Å3
264 parametersΔρmin = 0.18 e Å3
246 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0115 (19)
Special details top

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*/UeqOcc. (<1)
O10.29214 (15)1.3772 (3)0.36620 (9)0.0686 (6)
O20.47806 (13)0.7194 (4)0.39785 (8)0.0621 (5)
O30.44960 (17)1.1764 (4)0.20556 (10)0.0938 (8)
H30.45981.19330.17130.141*
N10.38789 (15)1.0564 (4)0.36671 (9)0.0501 (6)
N20.37331 (17)1.0161 (4)0.19729 (11)0.0630 (7)
C10.27605 (18)0.8280 (5)0.24993 (12)0.0510 (7)
H10.29860.70990.28400.061*
C20.21488 (18)0.7136 (5)0.18621 (13)0.0586 (7)
H2A0.21930.54370.18650.070*
H2B0.22700.77810.14870.070*
C30.12050 (19)0.8063 (4)0.19532 (12)0.0524 (7)
C40.18415 (19)0.9527 (5)0.25386 (13)0.0608 (8)
H4A0.18311.11990.24550.073*
H4B0.17080.92140.29350.073*
C50.33062 (19)1.2001 (5)0.39102 (12)0.0506 (7)
C60.32923 (17)1.0865 (4)0.45192 (11)0.0463 (6)
C70.2859 (2)1.1549 (5)0.49549 (13)0.0581 (7)
H70.24921.29140.48980.070*
C80.2991 (2)1.0109 (5)0.54867 (13)0.0619 (8)
H80.27071.05240.57930.074*
C90.35269 (19)0.8100 (5)0.55721 (12)0.0597 (8)
H90.35960.71740.59330.072*
C100.39679 (18)0.7416 (5)0.51341 (11)0.0524 (7)
H100.43300.60450.51910.063*
C110.38482 (17)0.8865 (4)0.46032 (11)0.0454 (6)
C120.42437 (18)0.8668 (5)0.40660 (12)0.0485 (7)
C130.4137 (2)1.1150 (5)0.30983 (11)0.0567 (7)
H13A0.48161.08030.31860.068*
H13B0.40501.28240.30210.068*
C140.35564 (19)0.9859 (5)0.24946 (12)0.0508 (7)
C150.0661 (2)0.6128 (5)0.21697 (17)0.0768 (9)
H15A0.11060.52380.25100.115*
H15B0.03550.51100.18130.115*
H15C0.01790.68160.23230.115*
C160.05588 (19)0.9572 (5)0.14145 (13)0.0574 (8)
C170.0427 (2)0.9725 (5)0.12865 (15)0.0676 (9)
H170.07160.87700.15150.081*
C180.0997 (3)1.1243 (7)0.08327 (19)0.0889 (12)
H180.16661.10980.06910.107*
C19A0.0559 (10)1.298 (3)0.0592 (8)0.093 (4)0.52 (3)
H19A0.09251.41690.03360.112*0.52 (3)
C20A0.0421 (9)1.293 (3)0.0734 (8)0.095 (4)0.52 (3)
H20A0.07211.40010.05420.114*0.52 (3)
C21A0.0980 (15)1.125 (3)0.1176 (8)0.077 (4)0.52 (3)
H21A0.16501.13210.13020.093*0.52 (3)
C19B0.0618 (14)1.210 (3)0.0355 (9)0.103 (4)0.48 (3)
H19B0.10231.27800.00210.124*0.48 (3)
C20B0.0305 (12)1.192 (4)0.0455 (9)0.103 (4)0.48 (3)
H20B0.05611.26510.01690.123*0.48 (3)
C21B0.0910 (15)1.072 (4)0.0959 (8)0.079 (4)0.48 (3)
H21B0.15641.06400.10080.095*0.48 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0918 (14)0.0610 (12)0.0553 (11)0.0149 (11)0.0273 (11)0.0140 (10)
O20.0676 (11)0.0782 (14)0.0460 (10)0.0170 (11)0.0262 (9)0.0037 (9)
O30.1143 (17)0.121 (2)0.0577 (13)0.0440 (15)0.0441 (13)0.0083 (13)
N10.0611 (12)0.0595 (14)0.0329 (10)0.0038 (11)0.0197 (10)0.0057 (10)
N20.0740 (15)0.0792 (16)0.0436 (12)0.0200 (13)0.0299 (12)0.0053 (11)
C10.0596 (15)0.0558 (16)0.0391 (13)0.0044 (12)0.0182 (12)0.0078 (11)
C20.0693 (17)0.0571 (16)0.0546 (16)0.0038 (14)0.0277 (14)0.0082 (13)
C30.0621 (15)0.0532 (16)0.0454 (14)0.0011 (13)0.0222 (13)0.0028 (12)
C40.0595 (16)0.079 (2)0.0440 (14)0.0038 (14)0.0168 (13)0.0114 (14)
C50.0583 (15)0.0564 (16)0.0368 (13)0.0030 (13)0.0149 (12)0.0004 (12)
C60.0506 (14)0.0550 (16)0.0343 (13)0.0009 (12)0.0153 (11)0.0014 (11)
C70.0669 (17)0.0646 (18)0.0481 (15)0.0039 (14)0.0259 (14)0.0031 (13)
C80.0712 (18)0.083 (2)0.0403 (14)0.0031 (17)0.0306 (14)0.0017 (15)
C90.0649 (16)0.079 (2)0.0365 (14)0.0042 (16)0.0180 (13)0.0092 (13)
C100.0559 (14)0.0656 (17)0.0365 (13)0.0027 (13)0.0162 (12)0.0092 (12)
C110.0486 (13)0.0559 (15)0.0325 (12)0.0012 (12)0.0145 (11)0.0001 (11)
C120.0494 (14)0.0580 (16)0.0375 (13)0.0010 (13)0.0137 (12)0.0034 (12)
C130.0697 (17)0.0701 (18)0.0366 (13)0.0087 (14)0.0258 (13)0.0042 (13)
C140.0616 (16)0.0614 (17)0.0346 (13)0.0020 (13)0.0229 (12)0.0032 (12)
C150.089 (2)0.068 (2)0.085 (2)0.0030 (17)0.0443 (19)0.0117 (17)
C160.0548 (17)0.0625 (18)0.0515 (16)0.0086 (14)0.0128 (14)0.0046 (13)
C170.0642 (19)0.077 (2)0.0610 (18)0.0088 (15)0.0198 (15)0.0073 (16)
C180.065 (2)0.113 (3)0.076 (2)0.002 (2)0.005 (2)0.001 (2)
C19A0.084 (5)0.113 (9)0.067 (7)0.001 (6)0.004 (6)0.031 (6)
C20A0.083 (5)0.112 (8)0.080 (8)0.014 (5)0.013 (6)0.035 (6)
C21A0.070 (5)0.106 (8)0.046 (7)0.015 (5)0.006 (6)0.020 (6)
C19B0.094 (6)0.122 (10)0.067 (7)0.016 (7)0.009 (6)0.003 (7)
C20B0.107 (6)0.135 (10)0.064 (7)0.021 (7)0.024 (7)0.039 (7)
C21B0.068 (6)0.115 (11)0.054 (8)0.001 (6)0.021 (7)0.035 (7)
Geometric parameters (Å, º) top
O1—C51.197 (3)C9—H90.9300
O2—C121.208 (3)C10—C111.392 (4)
O3—N21.408 (3)C10—H100.9300
O3—H30.8200C11—C121.479 (4)
N1—C121.384 (3)C13—C141.512 (4)
N1—C51.397 (4)C13—H13A0.9700
N1—C131.458 (3)C13—H13B0.9700
N2—C141.266 (4)C15—H15A0.9600
C1—C141.475 (4)C15—H15B0.9600
C1—C21.538 (3)C15—H15C0.9600
C1—C41.549 (4)C16—C21A1.33 (2)
C1—H10.9800C16—C171.381 (4)
C2—C31.553 (4)C16—C21B1.42 (2)
C2—H2A0.9700C17—C181.376 (4)
C2—H2B0.9700C17—H170.9300
C3—C161.517 (4)C18—C19A1.376 (15)
C3—C151.525 (4)C18—C19B1.424 (19)
C3—C41.560 (3)C18—H180.9300
C4—H4A0.9700C19A—C20A1.366 (19)
C4—H4B0.9700C19A—H19A0.9300
C5—C61.492 (4)C20A—C21A1.42 (2)
C6—C71.367 (4)C20A—H20A0.9300
C6—C111.377 (4)C21A—H21A0.9300
C7—C81.388 (4)C19B—C20B1.30 (2)
C7—H70.9300C19B—H19B0.9300
C8—C91.366 (4)C20B—C21B1.36 (2)
C8—H80.9300C20B—H20B0.9300
C9—C101.379 (4)C21B—H21B0.9300
N2—O3—H3109.5O2—C12—C11128.7 (3)
C12—N1—C5111.8 (2)N1—C12—C11105.9 (2)
C12—N1—C13124.5 (2)N1—C13—C14114.3 (2)
C5—N1—C13123.3 (2)N1—C13—H13A108.7
C14—N2—O3111.1 (2)C14—C13—H13A108.7
C14—C1—C2118.6 (3)N1—C13—H13B108.7
C14—C1—C4115.1 (2)C14—C13—H13B108.7
C2—C1—C489.24 (18)H13A—C13—H13B107.6
C14—C1—H1110.8N2—C14—C1119.0 (2)
C2—C1—H1110.8N2—C14—C13120.3 (2)
C4—C1—H1110.8C1—C14—C13120.6 (3)
C1—C2—C391.0 (2)C3—C15—H15A109.5
C1—C2—H2A113.5C3—C15—H15B109.5
C3—C2—H2A113.5H15A—C15—H15B109.5
C1—C2—H2B113.5C3—C15—H15C109.5
C3—C2—H2B113.5H15A—C15—H15C109.5
H2A—C2—H2B110.8H15B—C15—H15C109.5
C16—C3—C15113.4 (2)C21A—C16—C17117.5 (9)
C16—C3—C2116.5 (2)C21A—C16—C21B22.5 (9)
C15—C3—C2111.9 (2)C17—C16—C21B115.0 (8)
C16—C3—C4113.1 (2)C21A—C16—C3117.5 (8)
C15—C3—C4111.2 (3)C17—C16—C3122.6 (3)
C2—C3—C488.32 (19)C21B—C16—C3122.1 (8)
C1—C4—C390.3 (2)C18—C17—C16122.2 (3)
C1—C4—H4A113.6C18—C17—H17118.9
C3—C4—H4A113.6C16—C17—H17118.9
C1—C4—H4B113.6C17—C18—C19A118.8 (6)
C3—C4—H4B113.6C17—C18—C19B117.3 (7)
H4A—C4—H4B110.9C19A—C18—C19B29.1 (6)
O1—C5—N1124.9 (3)C17—C18—H18120.6
O1—C5—C6129.2 (3)C19A—C18—H18120.6
N1—C5—C6105.9 (2)C19B—C18—H18114.0
C7—C6—C11122.1 (2)C20A—C19A—C18119.0 (10)
C7—C6—C5130.5 (2)C20A—C19A—H19A120.5
C11—C6—C5107.3 (2)C18—C19A—H19A120.5
C6—C7—C8116.8 (3)C19A—C20A—C21A119.9 (13)
C6—C7—H7121.6C19A—C20A—H20A120.1
C8—C7—H7121.6C21A—C20A—H20A120.1
C9—C8—C7121.8 (3)C16—C21A—C20A121.1 (15)
C9—C8—H8119.1C16—C21A—H21A119.5
C7—C8—H8119.1C20A—C21A—H21A119.5
C8—C9—C10121.4 (3)C20B—C19B—C18118.8 (11)
C8—C9—H9119.3C20B—C19B—H19B120.6
C10—C9—H9119.3C18—C19B—H19B120.6
C9—C10—C11117.2 (3)C19B—C20B—C21B123.0 (16)
C9—C10—H10121.4C19B—C20B—H20B118.5
C11—C10—H10121.4C21B—C20B—H20B118.5
C6—C11—C10120.6 (3)C20B—C21B—C16121.0 (17)
C6—C11—C12108.9 (2)C20B—C21B—H21B119.5
C10—C11—C12130.4 (2)C16—C21B—H21B119.5
O2—C12—N1125.4 (3)
C14—C1—C2—C3126.7 (2)C5—N1—C13—C14102.0 (3)
C4—C1—C2—C38.3 (2)O3—N2—C14—C1178.5 (2)
C1—C2—C3—C16123.3 (2)O3—N2—C14—C130.1 (4)
C1—C2—C3—C15104.0 (3)C2—C1—C14—N22.4 (4)
C1—C2—C3—C48.2 (2)C4—C1—C14—N2106.2 (3)
C14—C1—C4—C3129.7 (2)C2—C1—C14—C13176.0 (2)
C2—C1—C4—C38.2 (2)C4—C1—C14—C1372.2 (3)
C16—C3—C4—C1126.4 (3)N1—C13—C14—N2177.8 (3)
C15—C3—C4—C1104.7 (3)N1—C13—C14—C13.9 (4)
C2—C3—C4—C18.2 (2)C15—C3—C16—C21A177.3 (10)
C12—N1—C5—O1178.6 (2)C2—C3—C16—C21A45.3 (10)
C13—N1—C5—O14.7 (4)C4—C3—C16—C21A54.9 (10)
C12—N1—C5—C61.2 (3)C15—C3—C16—C1720.8 (4)
C13—N1—C5—C6175.2 (2)C2—C3—C16—C17152.8 (3)
O1—C5—C6—C71.3 (4)C4—C3—C16—C17107.0 (3)
N1—C5—C6—C7178.6 (3)C15—C3—C16—C21B151.8 (11)
O1—C5—C6—C11179.7 (3)C2—C3—C16—C21B19.8 (11)
N1—C5—C6—C110.2 (3)C4—C3—C16—C21B80.4 (11)
C11—C6—C7—C81.0 (4)C21A—C16—C17—C1812.6 (10)
C5—C6—C7—C8179.2 (2)C21B—C16—C17—C1812.4 (11)
C6—C7—C8—C90.1 (4)C3—C16—C17—C18174.5 (3)
C7—C8—C9—C100.5 (4)C16—C17—C18—C19A13.2 (12)
C8—C9—C10—C110.3 (4)C16—C17—C18—C19B19.8 (11)
C7—C6—C11—C101.8 (4)C17—C18—C19A—C20A9.8 (16)
C5—C6—C11—C10179.7 (2)C19B—C18—C19A—C20A85 (3)
C7—C6—C11—C12177.8 (2)C18—C19A—C20A—C21A6.3 (18)
C5—C6—C11—C120.8 (3)C17—C16—C21A—C20A8.8 (14)
C9—C10—C11—C61.4 (3)C21B—C16—C21A—C20A81 (4)
C9—C10—C11—C12178.0 (2)C3—C16—C21A—C20A171.6 (9)
C5—N1—C12—O2177.8 (2)C19A—C20A—C21A—C166.0 (18)
C13—N1—C12—O24.0 (4)C17—C18—C19B—C20B17.0 (15)
C5—N1—C12—C111.7 (3)C19A—C18—C19B—C20B84 (2)
C13—N1—C12—C11175.6 (2)C18—C19B—C20B—C21B8 (2)
C6—C11—C12—O2178.0 (2)C19B—C20B—C21B—C160 (2)
C10—C11—C12—O21.5 (4)C21A—C16—C21B—C20B100 (5)
C6—C11—C12—N11.6 (3)C17—C16—C21B—C20B2.2 (17)
C10—C11—C12—N1179.0 (2)C3—C16—C21B—C20B175.3 (10)
C12—N1—C13—C1484.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O2i0.822.012.814 (3)165
C9—H9···N2ii0.932.593.522 (4)176
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x, y+3/2, z+1/2.
 

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