(4R,5R)-1,3-Dimethyl-4,5-diphenyl­imidazolidin-2-one

The title compound, C₁₇H₁₈N₂O, was obtained by methyl­ation of (4R,5R)-4,5-diphenyl­imidazolidin-2-one. The C-O bond exhibits double-bond character, and both C-N bonds in the urea group are inter­mediate between single and double bonds.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.083
• Data-to-parameter ratio = 10.5

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are meaningless.
           From the CIF: _refine_ls_abs_structure_Flack    0.000
           From the CIF: _refine_ls_abs_structure_Flack_su   10.000
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...      10.00
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..      10.00

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           27.50
           From the CIF: _reflns_number_total               1928
           Count of symmetry unique reflns         1927
           Completeness (_total/calc)            100.05%
           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 C2     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          R

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(4R,5R)-1,3-Dimethyl-4,5-diphenylimidazolidin-2-one

Crystal data

C17H18N2O	Dx = 1.210 Mg m^−3
Mr = 266.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 3626 reflections
a = 10.0509 (14) Å	θ = 2.4–27.3°
b = 10.3340 (15) Å	µ = 0.08 mm^−1
c = 14.075 (2) Å	T = 150 K
V = 1461.9 (4) Å^3	Prism, colourless
Z = 4	0.40 × 0.20 × 0.20 mm
F(000) = 568

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	1738 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
Graphite monochromator	θmax = 27.5°, θmin = 2.4°
φ and ω scans	h = −13→12
8831 measured reflections	k = −13→11
1928 independent reflections	l = −11→18

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0407P)^2 + 0.0934P] where P = (Fo^2 + 2Fc^2)/3
S = 1.18	(Δ/σ)max < 0.001
1928 reflections	Δρmax = 0.15 e Å^−3
183 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

Special details

Experimental. ¹H NMR (400 MHz, CDCl₃): δ 2.71 (6H, s, CH₃ × 2), 4.08 (2H, s, CH × 2), 7.13–7.15 (4H, m, Ar—H × 2), 7.34–7.37 (6H, m, Ar—H × 6).

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.91472 (16)	0.33061 (15)	0.55799 (12)	0.0296 (3)
C2	0.84530 (15)	0.48807 (14)	0.45034 (11)	0.0272 (3)
C3	0.94273 (15)	0.54948 (14)	0.52302 (11)	0.0259 (3)
C4	0.77131 (18)	0.25840 (17)	0.42709 (13)	0.0388 (4)
C5	1.03408 (19)	0.46026 (18)	0.67757 (13)	0.0401 (4)
C6	0.89635 (15)	0.67952 (14)	0.55897 (10)	0.0251 (3)
C7	0.78720 (15)	0.68842 (15)	0.61992 (11)	0.0288 (3)
C8	0.73946 (17)	0.80843 (17)	0.64748 (11)	0.0320 (3)
C9	0.80103 (19)	0.92042 (15)	0.61561 (11)	0.0333 (4)
C10	0.91038 (19)	0.91203 (16)	0.55703 (12)	0.0363 (4)
C11	0.95813 (17)	0.79204 (15)	0.52854 (11)	0.0325 (4)
C12	0.87133 (16)	0.52816 (15)	0.34883 (11)	0.0287 (3)
C13	0.96844 (16)	0.46667 (16)	0.29501 (11)	0.0319 (3)
C14	0.99630 (19)	0.50852 (18)	0.20330 (12)	0.0393 (4)
C15	0.9271 (2)	0.61198 (19)	0.16521 (13)	0.0446 (5)
C16	0.8301 (2)	0.67289 (19)	0.21787 (14)	0.0449 (5)
C17	0.80174 (19)	0.63116 (17)	0.30983 (13)	0.0374 (4)
N1	0.86506 (13)	0.35024 (12)	0.46760 (9)	0.0296 (3)
N2	0.94867 (14)	0.44881 (12)	0.59496 (10)	0.0300 (3)
O1	0.92646 (12)	0.22557 (11)	0.59695 (9)	0.0383 (3)
H2	0.7521	0.5120	0.4679	0.033*
H3	1.0323	0.5592	0.4929	0.031*
H4A	0.7849	0.2532	0.3582	0.047*
H4B	0.6802	0.2872	0.4402	0.047*
H4C	0.7856	0.1729	0.4555	0.047*
H5A	1.1249	0.4804	0.6571	0.048*
H5B	1.0011	0.5297	0.7187	0.048*
H5C	1.0339	0.3784	0.7127	0.048*
H7	0.7455	0.6119	0.6426	0.035*
H8	0.6644	0.8140	0.6883	0.038*
H9	0.7678	1.0027	0.6342	0.040*
H10	0.9534	0.9887	0.5360	0.044*
H11	1.0335	0.7871	0.4880	0.039*
H13	1.0161	0.3956	0.3210	0.038*
H14	1.0628	0.4661	0.1668	0.047*
H15	0.9465	0.6410	0.1027	0.053*
H16	0.7824	0.7436	0.1914	0.054*
H17	0.7346	0.6734	0.3459	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0272 (7)	0.0245 (7)	0.0372 (8)	0.0034 (6)	0.0052 (6)	−0.0034 (6)
C2	0.0264 (7)	0.0219 (7)	0.0333 (8)	−0.0003 (6)	−0.0003 (6)	−0.0039 (6)
C3	0.0239 (7)	0.0234 (7)	0.0303 (7)	0.0002 (6)	0.0013 (6)	−0.0029 (6)
C4	0.0387 (9)	0.0289 (8)	0.0488 (10)	−0.0093 (7)	0.0013 (8)	−0.0094 (7)
C5	0.0447 (10)	0.0365 (9)	0.0392 (9)	0.0083 (8)	−0.0134 (8)	−0.0030 (7)
C6	0.0275 (7)	0.0217 (7)	0.0261 (7)	0.0006 (6)	−0.0033 (6)	−0.0021 (6)
C7	0.0305 (8)	0.0246 (7)	0.0313 (7)	−0.0010 (6)	0.0016 (6)	−0.0013 (6)
C8	0.0328 (8)	0.0321 (8)	0.0313 (8)	0.0050 (7)	0.0006 (6)	−0.0044 (6)
C9	0.0444 (9)	0.0238 (7)	0.0317 (8)	0.0075 (7)	−0.0068 (7)	−0.0051 (6)
C10	0.0476 (10)	0.0224 (7)	0.0388 (9)	−0.0053 (7)	0.0011 (8)	0.0000 (7)
C11	0.0361 (8)	0.0282 (8)	0.0332 (8)	−0.0033 (7)	0.0053 (7)	−0.0022 (6)
C12	0.0289 (7)	0.0255 (7)	0.0316 (7)	−0.0055 (6)	−0.0055 (6)	−0.0037 (6)
C13	0.0325 (8)	0.0298 (8)	0.0335 (8)	−0.0050 (7)	−0.0027 (7)	−0.0043 (7)
C14	0.0422 (9)	0.0417 (10)	0.0340 (8)	−0.0137 (8)	0.0004 (7)	−0.0060 (8)
C15	0.0546 (12)	0.0448 (10)	0.0343 (9)	−0.0216 (9)	−0.0100 (8)	0.0038 (7)
C16	0.0498 (11)	0.0351 (9)	0.0497 (10)	−0.0091 (9)	−0.0197 (9)	0.0085 (8)
C17	0.0359 (9)	0.0310 (9)	0.0453 (9)	−0.0005 (7)	−0.0078 (8)	−0.0002 (7)
N1	0.0320 (7)	0.0216 (6)	0.0353 (7)	−0.0022 (5)	0.0011 (6)	−0.0045 (5)
N2	0.0331 (7)	0.0239 (6)	0.0331 (7)	0.0033 (5)	−0.0040 (6)	−0.0012 (5)
O1	0.0428 (7)	0.0239 (6)	0.0483 (7)	0.0055 (5)	0.0021 (6)	0.0024 (5)

Geometric parameters (Å, º)

C3—C2	1.552 (2)	N2—C5	1.450 (2)
C6—C3	1.510 (2)	O1—C1	1.222 (2)
C6—C7	1.396 (2)	C2—H2	1.0000
C6—C11	1.386 (2)	C3—H3	1.0000
C7—C8	1.385 (2)	C4—H4A	0.9800
C9—C8	1.387 (2)	C4—H4B	0.9800
C9—C10	1.377 (3)	C4—H4C	0.9800
C11—C10	1.389 (2)	C5—H5A	0.9800
C12—C2	1.510 (2)	C5—H5B	0.9800
C12—C13	1.389 (2)	C5—H5C	0.9800
C12—C17	1.387 (2)	C7—H7	0.9500
C13—C14	1.390 (2)	C8—H8	0.9500
C15—C14	1.384 (3)	C9—H9	0.9500
C15—C16	1.377 (3)	C10—H10	0.9500
C17—C16	1.394 (3)	C11—H11	0.9500
N1—C1	1.382 (2)	C13—H13	0.9500
N1—C2	1.458 (2)	C14—H14	0.9500
N1—C4	1.454 (2)	C15—H15	0.9500
N2—C1	1.371 (2)	C16—H16	0.9500
N2—C3	1.453 (2)	C17—H17	0.9500
C1—N1—C2	110.24 (12)	C6—C11—H11	119.8
C1—N1—C4	119.96 (13)	C7—C8—H8	119.9
C1—N2—C3	111.30 (13)	C8—C7—H7	119.9
C1—N2—C5	121.63 (14)	C8—C9—H9	120.1
C4—N1—C2	118.94 (14)	C9—C8—H8	119.9
C5—N2—C3	121.64 (14)	C9—C10—H10	119.8
C6—C3—C2	112.96 (12)	C10—C9—H9	120.1
C6—C11—C10	120.33 (15)	C10—C11—H11	119.8
C7—C6—C3	120.49 (13)	C11—C10—H10	119.8
C7—C8—C9	120.13 (15)	C12—C2—H2	109.1
C8—C7—C6	120.23 (15)	C12—C13—H13	119.8
C9—C10—C11	120.33 (15)	C12—C17—H17	119.9
C10—C9—C8	119.83 (15)	C13—C14—H14	120.0
C11—C6—C3	120.32 (13)	C14—C13—H13	119.8
C11—C6—C7	119.13 (14)	C14—C15—H15	120.0
C12—C2—C3	113.71 (12)	C15—C14—H14	120.0
C12—C17—C16	120.12 (18)	C15—C16—H16	119.9
C13—C12—C2	120.80 (15)	C16—C15—H15	120.0
C14—C13—C12	120.37 (16)	C16—C17—H17	119.9
C15—C14—C13	119.92 (17)	C17—C16—H16	119.9
C15—C16—C17	120.21 (18)	N1—C2—H2	109.1
C16—C15—C14	120.05 (17)	N1—C4—H4A	109.5
C17—C12—C2	119.84 (15)	N1—C4—H4B	109.5
C17—C12—C13	119.31 (15)	N1—C4—H4C	109.5
N1—C1—N2	107.98 (13)	N2—C3—H3	109.3
N1—C1—O1	125.35 (15)	N2—C5—H5A	109.5
N1—C2—C3	101.75 (12)	N2—C5—H5B	109.5
N1—C2—C12	113.69 (13)	N2—C5—H5C	109.5
N2—C1—O1	126.67 (15)	H4A—C4—H4B	109.5
N2—C3—C2	101.10 (12)	H4A—C4—H4C	109.5
N2—C3—C6	114.61 (13)	H4B—C4—H4C	109.5
C2—C3—H3	109.3	H5B—C5—H5A	109.5
C3—C2—H2	109.1	H5C—C5—H5A	109.5
C6—C3—H3	109.3	H5C—C5—H5B	109.5
C6—C7—H7	119.9
C1—N1—C2—C12	145.69 (13)	C6—C7—C8—C9	−0.9 (2)
C1—N1—C2—C3	23.02 (16)	C6—C11—C10—C9	−0.1 (3)
C1—N2—C3—C2	23.00 (16)	C7—C6—C3—C2	70.74 (18)
C1—N2—C3—C6	144.81 (13)	C7—C6—C3—N2	−44.35 (19)
C2—C12—C17—C16	176.70 (15)	C7—C6—C11—C10	−1.2 (2)
C2—C12—C13—C14	−176.74 (14)	C8—C9—C10—C11	1.0 (3)
C2—N1—C1—N2	−9.64 (17)	C10—C9—C8—C7	−0.5 (2)
C2—N1—C1—O1	170.76 (16)	C11—C6—C3—C2	−106.45 (16)
C3—C6—C7—C8	−175.57 (15)	C11—C6—C3—N2	138.46 (15)
C3—C6—C11—C10	176.07 (15)	C11—C6—C7—C8	1.7 (2)
C3—N2—C1—N1	−9.61 (17)	C12—C13—C14—C15	0.0 (2)
C3—N2—C1—O1	169.98 (16)	C12—C17—C16—C15	0.1 (3)
C4—N1—C1—N2	−153.53 (14)	C13—C12—C2—C3	82.49 (17)
C4—N1—C1—O1	26.9 (2)	C13—C12—C2—N1	−33.3 (2)
C4—N1—C2—C3	167.33 (13)	C13—C12—C17—C16	−0.5 (2)
C4—N1—C2—C12	−70.00 (19)	C14—C15—C16—C17	0.3 (3)
C5—N2—C1—N1	−163.96 (15)	C16—C15—C14—C13	−0.4 (3)
C5—N2—C1—O1	15.6 (3)	C17—C12—C2—C3	−94.71 (17)
C5—N2—C3—C2	177.34 (14)	C17—C12—C2—N1	149.47 (15)
C5—N2—C3—C6	−60.8 (2)	C17—C12—C13—C14	0.5 (2)
C6—C3—C2—C12	87.93 (16)	N2—C3—C2—C12	−149.12 (13)
C6—C3—C2—N1	−149.42 (13)	N2—C3—C2—N1	−26.46 (14)