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The title compound, C15H14N2O, is a chiral cyclic urea with an approximate local C2 axis. Adjacent mol­ecules are linked into chains through pairs of inter­molecular N—H...O hydrogen bonds, resulting in R22(8) loops.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806044382/hb2181sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806044382/hb2181Isup2.hkl
Contains datablock I

CCDC reference: 627781

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.100
  • Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
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 27.47 From the CIF: _reflns_number_total 1717 Count of symmetry unique reflns 1716 Completeness (_total/calc) 100.06% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C1 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 3 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 0 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: COLLECT (Nonius, 1999); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELXL97 and local procedures.

(4R,5R)-4,5-Diphenylimidazolidin-2-one top
Crystal data top
C15H14N2OF(000) = 504
Mr = 238.28Dx = 1.232 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1737 reflections
a = 7.123 (1) Åθ = 1.0–27.5°
b = 11.425 (2) ŵ = 0.08 mm1
c = 15.785 (2) ÅT = 90 K
V = 1284.6 (3) Å3Block, colorless
Z = 40.20 × 0.20 × 0.20 mm
Data collection top
Nonius KappaCCD
diffractometer
1717 independent reflections
Radiation source: fine-focus sealed tube1437 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 18 pixels mm-1θmax = 27.5°, θmin = 2.2°
ω scans at fixed χ = 55°h = 99
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)
k = 1414
Tmin = 0.984, Tmax = 0.984l = 2020
2958 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0561P)2 + 0.218P]
where P = (Fo2 + 2Fc2)/3
1717 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.22 e Å3
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*/Ueq
C10.3561 (3)0.44520 (17)0.36124 (12)0.0170 (4)
H10.38480.40460.30660.020*
C20.4627 (3)0.55933 (16)0.36459 (13)0.0180 (4)
C30.4646 (3)0.62731 (17)0.43780 (13)0.0222 (4)
H30.39500.60300.48600.027*
C40.5677 (3)0.73063 (19)0.44070 (15)0.0295 (5)
H40.56850.77660.49080.035*
C50.6693 (3)0.76642 (19)0.37064 (15)0.0299 (5)
H50.74010.83680.37270.036*
C60.6678 (3)0.69997 (18)0.29780 (14)0.0266 (5)
H60.73760.72470.24980.032*
C70.5648 (3)0.59714 (17)0.29436 (13)0.0217 (4)
H70.56370.55210.24380.026*
C80.2479 (3)0.31485 (16)0.46441 (13)0.0190 (4)
C90.1364 (3)0.45724 (18)0.37117 (13)0.0177 (4)
H90.10690.53320.39970.021*
C100.0323 (3)0.45129 (17)0.28752 (12)0.0175 (4)
C110.0638 (3)0.53845 (18)0.22747 (13)0.0222 (4)
H110.15020.59960.23940.027*
C120.0299 (3)0.53675 (19)0.15026 (13)0.0259 (5)
H120.00720.59630.10950.031*
C130.1565 (3)0.4479 (2)0.13283 (13)0.0272 (5)
H130.22150.44680.08030.033*
C140.1882 (3)0.36073 (19)0.19194 (13)0.0260 (5)
H140.27380.29930.17970.031*
C150.0949 (3)0.36285 (18)0.26922 (13)0.0207 (4)
H150.11850.30330.30990.025*
N10.4016 (2)0.36753 (15)0.43157 (11)0.0206 (4)
H1A0.51630.35620.45050.025*
N20.0938 (2)0.36139 (16)0.42874 (11)0.0241 (4)
H20.02090.33650.43910.029*
O10.2490 (2)0.23677 (12)0.51938 (9)0.0229 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0151 (9)0.0173 (9)0.0187 (9)0.0006 (8)0.0007 (8)0.0017 (8)
C20.0118 (8)0.0170 (9)0.0252 (10)0.0008 (8)0.0016 (9)0.0040 (8)
C30.0203 (10)0.0256 (10)0.0208 (10)0.0026 (9)0.0042 (9)0.0016 (8)
C40.0304 (12)0.0276 (11)0.0304 (11)0.0062 (10)0.0108 (11)0.0007 (9)
C50.0201 (10)0.0219 (10)0.0477 (14)0.0045 (9)0.0089 (11)0.0091 (10)
C60.0177 (10)0.0231 (10)0.0391 (13)0.0004 (9)0.0048 (10)0.0102 (10)
C70.0183 (10)0.0200 (9)0.0270 (11)0.0031 (8)0.0051 (9)0.0024 (8)
C80.0140 (9)0.0193 (9)0.0236 (10)0.0009 (8)0.0005 (9)0.0022 (8)
C90.0145 (9)0.0192 (9)0.0192 (9)0.0001 (8)0.0000 (8)0.0032 (9)
C100.0146 (9)0.0176 (9)0.0204 (9)0.0049 (8)0.0000 (8)0.0004 (8)
C110.0219 (10)0.0205 (10)0.0242 (10)0.0013 (9)0.0009 (9)0.0023 (9)
C120.0267 (11)0.0293 (11)0.0216 (10)0.0056 (10)0.0019 (10)0.0030 (9)
C130.0223 (10)0.0407 (12)0.0186 (10)0.0092 (10)0.0013 (10)0.0052 (10)
C140.0188 (10)0.0286 (11)0.0305 (11)0.0013 (9)0.0038 (9)0.0095 (10)
C150.0172 (10)0.0200 (9)0.0249 (10)0.0026 (8)0.0017 (9)0.0010 (8)
N10.0115 (8)0.0217 (8)0.0286 (9)0.0003 (7)0.0018 (8)0.0086 (8)
N20.0122 (8)0.0325 (9)0.0277 (9)0.0011 (7)0.0016 (8)0.0151 (9)
O10.0140 (7)0.0264 (7)0.0283 (8)0.0007 (6)0.0021 (7)0.0122 (6)
Geometric parameters (Å, º) top
C1—N11.458 (2)C8—N11.353 (3)
C1—C21.510 (3)C9—N21.455 (3)
C1—C91.579 (3)C9—C101.516 (3)
C1—H11.0000C9—H91.0000
C2—C31.392 (3)C10—C151.388 (3)
C2—C71.394 (3)C10—C111.393 (3)
C3—C41.391 (3)C11—C121.390 (3)
C3—H30.9500C11—H110.9500
C4—C51.383 (3)C12—C131.386 (3)
C4—H40.9500C12—H120.9500
C5—C61.378 (3)C13—C141.383 (3)
C5—H50.9500C13—H130.9500
C6—C71.386 (3)C14—C151.389 (3)
C6—H60.9500C14—H140.9500
C7—H70.9500C15—H150.9500
C8—O11.244 (2)N1—H1A0.8800
C8—N21.344 (3)N2—H20.8800
N1—C1—C2112.79 (16)C10—C9—C1113.22 (16)
N1—C1—C9101.41 (15)N2—C9—H9109.2
C2—C1—C9114.82 (17)C10—C9—H9109.2
N1—C1—H1109.2C1—C9—H9109.2
C2—C1—H1109.2C15—C10—C11118.95 (19)
C9—C1—H1109.2C15—C10—C9122.23 (18)
C3—C2—C7118.82 (17)C11—C10—C9118.81 (18)
C3—C2—C1121.04 (17)C12—C11—C10120.6 (2)
C7—C2—C1120.13 (17)C12—C11—H11119.7
C4—C3—C2120.4 (2)C10—C11—H11119.7
C4—C3—H3119.8C13—C12—C11119.8 (2)
C2—C3—H3119.8C13—C12—H12120.1
C5—C4—C3120.0 (2)C11—C12—H12120.1
C5—C4—H4120.0C14—C13—C12119.99 (19)
C3—C4—H4120.0C14—C13—H13120.0
C6—C5—C4120.0 (2)C12—C13—H13120.0
C6—C5—H5120.0C13—C14—C15120.1 (2)
C4—C5—H5120.0C13—C14—H14119.9
C5—C6—C7120.3 (2)C15—C14—H14119.9
C5—C6—H6119.9C10—C15—C14120.5 (2)
C7—C6—H6119.9C10—C15—H15119.7
C6—C7—C2120.5 (2)C14—C15—H15119.7
C6—C7—H7119.8C8—N1—C1112.51 (15)
C2—C7—H7119.8C8—N1—H1A123.7
O1—C8—N2125.51 (19)C1—N1—H1A123.7
O1—C8—N1125.54 (19)C8—N2—C9112.89 (16)
N2—C8—N1108.95 (15)C8—N2—H2123.6
N2—C9—C10114.09 (16)C9—N2—H2123.6
N2—C9—C1101.73 (16)
N1—C1—C2—C351.3 (2)N2—C9—C10—C11179.58 (17)
C9—C1—C2—C364.2 (2)C1—C9—C10—C1163.8 (2)
N1—C1—C2—C7127.35 (19)C15—C10—C11—C120.3 (3)
C9—C1—C2—C7117.1 (2)C9—C10—C11—C12179.47 (18)
C7—C2—C3—C40.4 (3)C10—C11—C12—C130.3 (3)
C1—C2—C3—C4178.18 (19)C11—C12—C13—C140.5 (3)
C2—C3—C4—C50.0 (3)C12—C13—C14—C150.8 (3)
C3—C4—C5—C60.2 (3)C11—C10—C15—C140.6 (3)
C4—C5—C6—C70.0 (3)C9—C10—C15—C14179.71 (18)
C5—C6—C7—C20.5 (3)C13—C14—C15—C100.8 (3)
C3—C2—C7—C60.7 (3)O1—C8—N1—C1173.04 (18)
C1—C2—C7—C6177.97 (18)N2—C8—N1—C17.6 (2)
N1—C1—C9—N214.9 (2)C2—C1—N1—C8137.67 (17)
C2—C1—C9—N2136.79 (17)C9—C1—N1—C814.4 (2)
N1—C1—C9—C10137.75 (16)O1—C8—N2—C9175.60 (17)
C2—C1—C9—C10100.3 (2)N1—C8—N2—C93.7 (2)
N2—C9—C10—C151.3 (3)C10—C9—N2—C8134.37 (19)
C1—C9—C10—C15117.0 (2)C1—C9—N2—C812.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.882.022.853 (2)157
N2—H2···O1ii0.881.952.821 (2)168
Symmetry codes: (i) x+1/2, y+1/2, z+1; (ii) x1/2, y+1/2, z+1.
 

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