1,3,5-Tri-p-tolyl­biuret

MoOCl₂(L_OMe) as catalyst, where L_OMe is CpCo[P(O)(OMe)₂]₃, reacts with p-tolyl isocyanate to afford the title compound, C₂₃H₂₃N₃O₂. The structural features are the intramolecular hydrogen bond forming a six-membered ring and a nearly planar arrangement of the biuret moiety. Each p-tolyl phenyl ring is twisted by approximately 60-80° with respect to the others. The bond lengths N1-C22 of 1.357 (3) Å and N2-C23 of 1.333 (3) Å indicate that they are partial double bonds.

Computing details

Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C23H23N3O2	Dx = 1.226 Mg m^−3
Mr = 373.44	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 9.7626 (6) Å	θ = 11.2–13.8°
b = 12.4280 (8) Å	µ = 0.08 mm^−1
c = 16.6770 (7) Å	T = 293 K
V = 2023.4 (2) Å^3	Tetragonal rod, colourless
Z = 4	0.50 × 0.45 × 0.45 mm
F(000) = 792

Data collection

CAD-4 diffractometer	Rint = 0.006
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.0°
Graphite monochromator	h = −12→0
ω/2θ scans	k = 0→15
2308 measured reflections	l = 0→20
2263 independent reflections	2 standard reflections every 60 min
1501 reflections with I > 2σ(I)	intensity decay: 0.3%

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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0615P)^2P] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max < 0.001
2263 reflections	Δρmax = 0.12 e Å^−3
262 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.17347 (19)	0.43712 (14)	0.81849 (12)	0.0746 (5)
O2	0.3836 (2)	0.16374 (14)	0.88300 (14)	0.0959 (7)
N1	0.0323 (2)	0.40041 (16)	0.92202 (15)	0.0655 (6)
H1N	0.023 (4)	0.363 (2)	0.9582 (18)	0.089 (11)*
N2	0.3909 (2)	0.31527 (15)	0.80727 (13)	0.0606 (5)
H2N	0.334 (3)	0.377 (2)	0.7930 (17)	0.097 (10)*
N3	0.2003 (2)	0.27766 (14)	0.88748 (12)	0.0619 (5)
C1	−0.0506 (2)	0.49432 (16)	0.91564 (14)	0.0532 (5)
C2	−0.0793 (2)	0.55223 (18)	0.98375 (15)	0.0577 (6)
H2	−0.0410	0.5319	1.0325	0.069*
C3	−0.1652 (3)	0.64093 (18)	0.97990 (15)	0.0621 (6)
H3	−0.1851	0.6790	1.0265	0.074*
C4	−0.2217 (2)	0.67354 (18)	0.90814 (15)	0.0594 (6)
C5	−0.1922 (3)	0.6139 (2)	0.84004 (15)	0.0677 (7)
H5	−0.2306	0.6337	0.7912	0.081*
C6	−0.1066 (3)	0.5255 (2)	0.84382 (15)	0.0661 (7)
H6	−0.0868	0.4869	0.7975	0.079*
C7	−0.3127 (3)	0.7718 (2)	0.90410 (17)	0.0850 (8)
H7A	−0.3208	0.8029	0.9566	0.127*
H7B	−0.4018	0.7513	0.8851	0.127*
H7C	−0.2733	0.8235	0.8681	0.127*
C8	0.1259 (2)	0.19601 (17)	0.93088 (15)	0.0584 (6)
C9	0.1623 (3)	0.1666 (2)	1.00739 (16)	0.0644 (7)
H9	0.2343	0.2010	1.0334	0.077*
C10	0.0908 (3)	0.0854 (2)	1.04500 (16)	0.0733 (7)
H10	0.1173	0.0644	1.0962	0.088*
C11	−0.0183 (3)	0.03442 (19)	1.00941 (19)	0.0744 (8)
C12	−0.0551 (3)	0.0676 (2)	0.9340 (2)	0.0829 (8)
H12	−0.1304	0.0359	0.9093	0.099*
C13	0.0162 (3)	0.1462 (2)	0.89376 (16)	0.0723 (8)
H13	−0.0091	0.1658	0.8420	0.087*
C14	−0.0927 (4)	−0.0550 (2)	1.0517 (2)	0.1121 (13)
H14A	−0.0614	−0.1231	1.0315	0.168*
H14B	−0.1893	−0.0482	1.0423	0.168*
H14C	−0.0748	−0.0509	1.1082	0.168*
C15	0.5221 (2)	0.30789 (17)	0.77152 (13)	0.0550 (6)
C16	0.5677 (2)	0.39712 (19)	0.73023 (13)	0.0594 (6)
H16	0.5132	0.4584	0.7277	0.071*
C17	0.6937 (3)	0.3961 (2)	0.69267 (14)	0.0629 (6)
H17	0.7236	0.4574	0.6659	0.075*
C18	0.7762 (2)	0.3059 (2)	0.69396 (14)	0.0629 (6)
C19	0.7288 (3)	0.2174 (2)	0.73444 (16)	0.0698 (7)
H19	0.7827	0.1557	0.7357	0.084*
C20	0.6039 (3)	0.21652 (18)	0.77351 (15)	0.0653 (6)
H20	0.5749	0.1554	0.8008	0.078*
C21	0.9147 (3)	0.3042 (3)	0.65307 (19)	0.0928 (9)
H21A	0.9327	0.2333	0.6329	0.139*
H21B	0.9845	0.3238	0.6910	0.139*
H21C	0.9149	0.3546	0.6094	0.139*
C22	0.1373 (2)	0.37676 (18)	0.87179 (16)	0.0597 (6)
C23	0.3332 (3)	0.24727 (19)	0.85904 (16)	0.0637 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0643 (10)	0.0632 (10)	0.0962 (13)	0.0121 (9)	0.0121 (10)	0.0172 (10)
O2	0.0777 (13)	0.0605 (10)	0.1496 (19)	0.0179 (10)	0.0339 (14)	0.0286 (12)
N1	0.0618 (13)	0.0520 (11)	0.0826 (15)	0.0053 (10)	0.0027 (13)	0.0093 (12)
N2	0.0548 (11)	0.0518 (10)	0.0752 (13)	0.0053 (10)	0.0017 (11)	0.0010 (10)
N3	0.0554 (11)	0.0470 (10)	0.0834 (13)	0.0006 (9)	0.0012 (11)	0.0012 (10)
C1	0.0436 (11)	0.0461 (11)	0.0701 (14)	−0.0022 (10)	−0.0007 (12)	0.0026 (11)
C2	0.0560 (14)	0.0589 (13)	0.0582 (14)	−0.0036 (12)	−0.0036 (12)	0.0067 (11)
C3	0.0655 (14)	0.0573 (13)	0.0634 (14)	0.0009 (12)	0.0082 (13)	0.0003 (11)
C4	0.0510 (12)	0.0580 (13)	0.0693 (15)	0.0038 (11)	−0.0038 (12)	0.0052 (12)
C5	0.0619 (15)	0.0784 (15)	0.0629 (14)	0.0099 (15)	−0.0144 (12)	−0.0021 (13)
C6	0.0633 (14)	0.0678 (14)	0.0673 (15)	0.0035 (14)	−0.0057 (13)	−0.0120 (12)
C7	0.0828 (19)	0.0784 (17)	0.0936 (19)	0.0265 (16)	−0.0028 (17)	0.0044 (16)
C8	0.0545 (12)	0.0463 (11)	0.0744 (15)	0.0040 (11)	0.0038 (12)	−0.0021 (11)
C9	0.0595 (14)	0.0649 (14)	0.0688 (16)	0.0106 (13)	−0.0030 (13)	−0.0053 (12)
C10	0.0795 (18)	0.0716 (16)	0.0688 (15)	0.0239 (16)	0.0136 (15)	0.0047 (13)
C11	0.0790 (19)	0.0502 (13)	0.094 (2)	0.0099 (14)	0.0283 (17)	−0.0018 (13)
C12	0.0793 (18)	0.0633 (15)	0.106 (2)	−0.0180 (15)	−0.0040 (18)	−0.0015 (15)
C13	0.0768 (18)	0.0625 (15)	0.0775 (17)	−0.0115 (14)	−0.0097 (15)	0.0065 (13)
C14	0.129 (3)	0.0682 (17)	0.139 (3)	−0.005 (2)	0.057 (3)	0.0152 (18)
C15	0.0533 (13)	0.0541 (12)	0.0575 (13)	−0.0009 (11)	−0.0036 (11)	−0.0083 (11)
C16	0.0610 (14)	0.0554 (13)	0.0618 (13)	0.0060 (12)	−0.0041 (13)	−0.0043 (12)
C17	0.0649 (15)	0.0648 (14)	0.0591 (13)	−0.0026 (13)	−0.0020 (13)	−0.0029 (12)
C18	0.0565 (14)	0.0717 (15)	0.0605 (13)	0.0025 (13)	0.0004 (12)	−0.0095 (13)
C19	0.0633 (15)	0.0668 (15)	0.0794 (16)	0.0162 (14)	−0.0035 (14)	−0.0114 (15)
C20	0.0663 (15)	0.0492 (12)	0.0803 (16)	0.0053 (12)	0.0031 (14)	−0.0036 (12)
C21	0.0671 (18)	0.113 (2)	0.098 (2)	0.0086 (19)	0.0165 (17)	−0.0054 (18)
C22	0.0525 (14)	0.0489 (12)	0.0778 (15)	−0.0012 (11)	−0.0051 (13)	−0.0005 (12)
C23	0.0595 (14)	0.0483 (12)	0.0833 (17)	0.0031 (12)	0.0062 (14)	−0.0009 (12)

Geometric parameters (Å, º)

O1—C22	1.215 (3)	C5—C6	1.382 (3)
O2—C23	1.216 (3)	C8—C9	1.374 (4)
N1—C22	1.357 (3)	C8—C13	1.383 (4)
N1—C1	1.424 (3)	C9—C10	1.378 (4)
N2—C23	1.333 (3)	C10—C11	1.374 (4)
N2—C15	1.417 (3)	C11—C12	1.372 (4)
N3—C22	1.401 (3)	C11—C14	1.503 (4)
N3—C23	1.432 (3)	C12—C13	1.375 (4)
N3—C8	1.442 (3)	C15—C16	1.379 (3)
C1—C6	1.372 (3)	C15—C20	1.388 (3)
C1—C2	1.373 (3)	C16—C17	1.380 (4)
C2—C3	1.387 (3)	C17—C18	1.380 (3)
C3—C4	1.378 (3)	C18—C19	1.371 (4)
C4—C5	1.386 (3)	C18—C21	1.515 (3)
C4—C7	1.512 (3)	C19—C20	1.383 (4)
C22—N1—C1	124.1 (2)	C12—C11—C14	121.7 (3)
C23—N2—C15	127.9 (2)	C10—C11—C14	120.8 (3)
C22—N3—C23	124.6 (2)	C11—C12—C13	121.9 (3)
C22—N3—C8	119.4 (2)	C12—C13—C8	119.5 (3)
C23—N3—C8	115.89 (18)	C16—C15—C20	119.0 (2)
C6—C1—C2	119.5 (2)	C16—C15—N2	116.7 (2)
C6—C1—N1	121.5 (2)	C20—C15—N2	124.3 (2)
C2—C1—N1	118.9 (2)	C15—C16—C17	120.4 (2)
C1—C2—C3	120.1 (2)	C18—C17—C16	121.3 (2)
C4—C3—C2	121.0 (2)	C19—C18—C17	117.5 (2)
C3—C4—C5	118.1 (2)	C19—C18—C21	120.8 (2)
C3—C4—C7	120.7 (2)	C17—C18—C21	121.7 (3)
C5—C4—C7	121.1 (2)	C18—C19—C20	122.4 (2)
C6—C5—C4	120.9 (2)	C19—C20—C15	119.3 (2)
C1—C6—C5	120.3 (2)	O1—C22—N1	122.5 (2)
C9—C8—C13	119.8 (2)	O1—C22—N3	123.5 (2)
C9—C8—N3	121.5 (2)	N1—C22—N3	114.0 (2)
C13—C8—N3	118.7 (2)	O2—C23—N2	125.7 (2)
C8—C9—C10	119.1 (2)	O2—C23—N3	118.9 (2)
C11—C10—C9	122.3 (3)	N2—C23—N3	115.5 (2)
C12—C11—C10	117.4 (3)