N-{2-[(4S)-4-tert-Butyl-4,5-dihydro-1,3-oxazol-2-yl]phen­yl}-5,6-diphenyl-1,2,4-triazin-3-amine

Karczmarzyk, Z.; Wolińska, E.; Fruziński, A.

doi:10.1107/S1600536811005411

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o651

doi:10.1107/S1600536811005411

Open

access

N-{2-[(4S)-4-tert-Butyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}-5,6-diphenyl-1,2,4-triazin-3-amine

Zbigniew Karczmarzyk,^a ^* Ewa Wolińska ^a and Andrzej Fruziński ^b

^aDepartment of Chemistry, University of Podlasie, ul. 3 Maja 54, 08-110 Siedlce, Poland, and ^bDepartment of General and Ecological Chemistry, Technical University, ul. Żeromskiego 115, 90-924 Łódź, Poland
^*Correspondence e-mail: kar@uph.edu.pl

(Received 7 February 2011; accepted 14 February 2011; online 19 February 2011)

The title compound, C₂₈H₂₇N₅O, was synthesized using palladium cross-coupling amination of 3-bromo-5,6-diphenyl-1,2,4-triazine with 2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]aniline. The oxazoline ring is almost planar, with a maximum atomic deviation of 0.023 (5) Å. The phenyl rings make dihedral angles of 29.0 (1) and 54.6 (1)° with the triazine ring while the benzene ring makes a dihedral angle of 0.6 (1)° with the oxazoline ring. The conformation of the molecule is influenced by strong intramolecular N—H⋯N and weak C—H⋯N hydrogen bonds. In the crystal, screw-axis related molecules are linked into supramolecular chains by intermolecular C—H⋯O hydrogen bonds. π–π stacking is observed between the oxazoline and triazine rings of adjacent molecules, with a centroid–centroid distance of 3.749 (2) Å.

Related literature

For applications of compounds containing a chiral oxazoline ring in asymmetric catalysis, see: Lindsey & Layton (2004 ); Desimoni et al. (2006 ); Hargaden & Guiry (2009 ). For related structures, see: Castro et al. (2001 ); Coeffard et al. (2009 ).

Experimental

Crystal data

C₂₈H₂₇N₅O
M_r = 449.55
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.3306 (2) Å
b = 16.9244 (6) Å
c = 22.5787 (8) Å
V = 2419.12 (14) Å³
Z = 4
Cu Kα radiation
μ = 0.61 mm⁻¹
T = 293 K
0.54 × 0.02 × 0.02 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.882, T_max = 1.000
28527 measured reflections
2625 independent reflections
1648 reflections with I > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.134
S = 1.05
2625 reflections
311 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯N15	0.97 (4)	1.87 (5)	2.671 (4)	138 (4)
C13—H13⋯N2	0.93	2.31	2.919 (5)	122
C53—H53⋯O18ⁱ	0.93	2.54	3.250 (5)	133
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005411/xu5158sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005411/xu5158Isup2.hkl

checkCIF report

Comment top

Compounds containing a chiral oxazoline ring have proven to be one of the most successful ligand classes for asymmetric catalysis. A diverse range of di-, tri- and tetradentate oxazoline ligands incorporating various heteroatoms and specific structural features have been synthesized and used in a wide range of metal catalyzed asymmetric processes (Desimoni et al., 2006; Hargaden et al., 2009). Introduction of 1,2,4-triazine ring into ligand structure can significantly increase ligand binding properties, since 1,2,4-triazine is known as a good metal chelator (Lindsey et al., 2004). Due to our interest in developing new oxazoline-based ligands the titled compound was synthesized and its application in asymmetric catalysis is currently under investigation.

The central secondary N7-amine group is planar with the sum of the angles around N atom of 359.1°. The unusually large C3—N7—C8 angle of 131.1 (3)° is constrained by the strong N7—H7···N15 intramolecular hydrogen bond (Table 1), which forced a cis-cis conformation of the amine spacer between 1,2,4-triazine ring and the (oxazolyl)phenyl group with the torsion angles N2—C3—N7—C8 and C3—N7—C8—C13 of 3.9 (6) and –12.4 (6)°, respectively. The similar geometry and conformation of the [(oxazolyl)phenyl]amine subunit have been reported in closely related structures (Castro et al., 2001; Coeffard et al., 2009). The 5- and 6-phenyl substituents of the 1,2,4-triazine ring are inclined to its mean plane with the dihedral angle of 29.0 (1) and 54.6 (1)°, respectively.

In the crystal structure, Fig. 2, the screw-related molecules are linked into chains along the [010] direction by C53—H53···O18 intermolecular hydrogen bond (Table 1). Additionally, the π-electron systems of the oxazoline and triazine rings belonging to the translation-related molecules overlap each other, with centroid-to-centroid separation of 3.749 (2) Å between the oxazoline ring at (x, y, z) and triazine ring at (1+x, y, z), and triazine ring at (x, y, z) and oxazoline ring at (–1+x, y, z). The π···π distances are 3.2389 (16) and 3.4927 (13) Å, respectively.

Related literature top

For applications of compounds containing a chiral oxazoline ring in asymmetric catalysis, see: Lindsey & Layton (2004); Desimoni et al. (2006); Hargaden & Guiry (2009). For related structures, see: Castro et al. (2001); Coeffard et al. (2009).

Experimental top

The titled compound was synthesized using palladium cross-coupling amination of 5,6-diphenyl-3-bromo-1,2,4-triazine with readily available 2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]aniline as the key step. An oven dried three-necked flask was washed with argon and charged with Pd₂dba₃ (45.7 mg, 0.05 mmol), Xantphos (57.8 mg, 0.1 mmol), 2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]aniline (0.131 g, 0.6 mmol), 3-bromo-5,6-diphenyl-1,2,4-triazine (155 mg, 0.5 mmol) and K₂CO₃ (1.38g, 10 mmol). Then, the flask was evacuated and backfilled with argon. Dioxane (10 ml) was added trough the septum. The mixture was refluxed for 24 hours. After cooling, the solid material was filtered off and washed with CH₂Cl₂. The solvent was evaporated, and the resulting crude product was purified by column chromatography using hexanes/ethyl acetate (10:1) as eluent. Product was recrystalized from ethanol to give 5,6-diphenyl-3-{2-[(4S)-4-tert-butyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}amino-1,2,4-triazine as a yellow crystals; yield: 0.095 g, 42%; mp 489-490 K; [α]_D²⁰of –15.69°. Crystals suitable for X-ray diffraction analysis were grown by slow evaporation of a methanol solution.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A view of the molecular packing in (I). Dashed lines indicate weak C—H···O intermolecular interaction [symmetry code: (i) –x+1, y–1/2, –z+3/2].

N-{2-[(4S)-4-tert-Butyl-4,5-dihydro-1,3-oxazol- 2-yl]phenyl}-5,6-diphenyl-1,2,4-triazin-3-amine top

Crystal data top

C₂₈H₂₇N₅O	D_x = 1.234 Mg m⁻³
M_r = 449.55	Melting point = 489–490 K
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1210 reflections
a = 6.3306 (2) Å	θ = 4.6–30.0°
b = 16.9244 (6) Å	µ = 0.61 mm⁻¹
c = 22.5787 (8) Å	T = 293 K
V = 2419.12 (14) Å³	Needle, yellow
Z = 4	0.54 × 0.02 × 0.02 mm
F(000) = 952

Data collection top

Bruker SMART APEXII CCD diffractometer	2625 independent reflections
Radiation source: fine-focus sealed tube	1648 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
ω scans	θ_max = 70.2°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→6
T_min = 0.882, T_max = 1.000	k = −20→20
28527 measured reflections	l = −27→27

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.134	w = 1/[σ²(F_o²) + (0.0683P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2625 reflections	Δρ_max = 0.15 e Å⁻³
311 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0053 (5)

Crystal data top

C₂₈H₂₇N₅O	V = 2419.12 (14) Å³
M_r = 449.55	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 6.3306 (2) Å	µ = 0.61 mm⁻¹
b = 16.9244 (6) Å	T = 293 K
c = 22.5787 (8) Å	0.54 × 0.02 × 0.02 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2625 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1648 reflections with I > 2σ(I)
T_min = 0.882, T_max = 1.000	R_int = 0.090
28527 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.15 e Å⁻³
2625 reflections	Δρ_min = −0.17 e Å⁻³
311 parameters

Special details top

Experimental. ¹H NMR (400 MHz, CDCl3) δ: 1.05 (s, 9H, (CH₃)₃C), 4.25–4.35 (m, 2H, (CH₂O and CHN), 4.45–4.50 (m, 1H, CH₂O), 7.11 (t, 1H, J = 7.6 Hz, Ph), 7.31–7.37 (m, 5H, Ph), 7.42–7.44 (m, 1H, Ph), 7.50–7.52 (m, 2H, Ph), 7.56–7.60 (m, 3H, Ph), 7.91 (d, 1H, J = 7.6 Hz, Ph), 8.89 (d, 1H, J = 8.4 Hz, Ph), 12.98 (s, 1H, NH); ¹³C NMR (50 MHz, CDCl₃) δ: 25.9, 34.0, 67.5, 76.1, 112.8, 118.9, 120.7, 128.2, 128.3, 128.6, 129.2, 129.3, 129.8, 130.4, 132.3, 136.0, 136.1, 140.8, 150.8, 156.0, 158.8, 163.4; Analysis calculated for C₂₈H₂₇N₅O: C 74.81; H 6.05; N 15.58; found: C 74.79; H 6.03; N 15.51.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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

	x	y	z	U_iso*/U_eq
O18	0.9330 (4)	0.61773 (16)	0.78505 (12)	0.0793 (8)
N1	−0.0592 (5)	0.54476 (19)	0.97426 (12)	0.0735 (9)
N2	0.0979 (5)	0.58502 (18)	0.94731 (14)	0.0728 (9)
N4	0.1210 (5)	0.48257 (17)	0.87487 (12)	0.0640 (8)
N7	0.3575 (5)	0.58275 (18)	0.87252 (13)	0.0697 (9)
H7	0.411 (8)	0.548 (2)	0.8420 (18)	0.105*
N15	0.6459 (5)	0.54077 (19)	0.79214 (13)	0.0716 (9)
C3	0.1856 (6)	0.5505 (2)	0.90057 (16)	0.0611 (9)
C5	−0.0365 (6)	0.4448 (2)	0.90072 (15)	0.0578 (9)
C6	−0.1237 (6)	0.4751 (2)	0.95379 (15)	0.0613 (9)
C8	0.4787 (6)	0.6496 (2)	0.88589 (15)	0.0647 (10)
C9	0.6707 (6)	0.6585 (2)	0.85444 (16)	0.0637 (10)
C10	0.7987 (7)	0.7239 (2)	0.86881 (17)	0.0784 (11)
H10	0.9268	0.7306	0.8493	0.118*
C11	0.7389 (8)	0.7781 (3)	0.91095 (19)	0.0894 (14)
H11	0.8266	0.8205	0.9200	0.134*
C12	0.5491 (8)	0.7693 (2)	0.93957 (18)	0.0828 (12)
H12	0.5080	0.8064	0.9677	0.124*
C13	0.4183 (8)	0.7061 (2)	0.92720 (16)	0.0780 (12)
H13	0.2893	0.7014	0.9466	0.117*
C14	0.7399 (6)	0.6022 (2)	0.80992 (16)	0.0647 (10)
C16	0.7797 (6)	0.5003 (2)	0.74766 (16)	0.0668 (10)
H16	0.8305	0.4509	0.7653	0.100*
C17	0.9690 (7)	0.5565 (3)	0.74209 (19)	0.0855 (12)
H171	1.0999	0.5289	0.7504	0.128*
H172	0.9764	0.5786	0.7025	0.128*
C19	0.6617 (6)	0.4794 (2)	0.69076 (17)	0.0741 (11)
C20	0.4820 (8)	0.4227 (3)	0.7063 (2)	0.1036 (15)
H201	0.3925	0.4466	0.7357	0.155*
H202	0.5398	0.3744	0.7217	0.155*
H203	0.4007	0.4115	0.6714	0.155*
C21	0.8171 (9)	0.4373 (3)	0.64968 (19)	0.1075 (16)
H211	0.8815	0.3940	0.6704	0.161*
H212	0.9243	0.4737	0.6371	0.161*
H213	0.7429	0.4176	0.6157	0.161*
C22	0.5743 (10)	0.5535 (3)	0.6608 (2)	0.1179 (18)
H221	0.6884	0.5888	0.6516	0.177*
H222	0.4769	0.5793	0.6870	0.177*
H223	0.5026	0.5389	0.6250	0.177*
C51	−0.1113 (6)	0.3731 (2)	0.86873 (14)	0.0588 (9)
C52	0.0351 (7)	0.3342 (2)	0.83248 (16)	0.0694 (11)
H52	0.1747	0.3513	0.8317	0.104*
C53	−0.0247 (7)	0.2709 (2)	0.7979 (2)	0.0833 (12)
H53	0.0742	0.2456	0.7741	0.125*
C54	−0.2320 (7)	0.2451 (2)	0.7986 (2)	0.0828 (12)
H54	−0.2729	0.2026	0.7751	0.124*
C55	−0.3780 (7)	0.2826 (2)	0.83435 (18)	0.0802 (12)
H55	−0.5171	0.2650	0.8351	0.120*
C56	−0.3186 (6)	0.3463 (2)	0.86901 (16)	0.0684 (10)
H56	−0.4184	0.3713	0.8927	0.103*
C61	−0.2858 (6)	0.4352 (2)	0.99015 (15)	0.0676 (10)
C62	−0.2523 (8)	0.3591 (2)	1.01024 (18)	0.0882 (13)
H62	−0.1272	0.3328	1.0013	0.132*
C63	−0.4080 (12)	0.3219 (4)	1.0441 (2)	0.119 (2)
H63	−0.3863	0.2707	1.0579	0.179*
C64	−0.5935 (11)	0.3607 (5)	1.0572 (2)	0.133 (3)
H64	−0.6972	0.3355	1.0794	0.200*
C65	−0.6258 (9)	0.4369 (4)	1.0375 (2)	0.1133 (19)
H65	−0.7513	0.4631	1.0460	0.170*
C66	−0.4700 (6)	0.4739 (3)	1.00486 (17)	0.0838 (13)
H66	−0.4897	0.5258	0.9926	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O18	0.0671 (17)	0.0869 (18)	0.0839 (17)	−0.0114 (14)	0.0118 (14)	0.0045 (16)
N1	0.079 (2)	0.074 (2)	0.068 (2)	−0.0071 (18)	0.0151 (17)	−0.0099 (17)
N2	0.078 (2)	0.072 (2)	0.0678 (19)	−0.0101 (17)	0.0166 (17)	−0.0130 (17)
N4	0.0636 (19)	0.0691 (19)	0.0592 (17)	−0.0067 (16)	0.0089 (15)	−0.0032 (15)
N7	0.072 (2)	0.070 (2)	0.067 (2)	−0.0153 (17)	0.0156 (17)	−0.0113 (16)
N15	0.074 (2)	0.073 (2)	0.0673 (19)	−0.0073 (18)	0.0152 (17)	−0.0071 (17)
C3	0.062 (2)	0.063 (2)	0.058 (2)	−0.0057 (19)	0.0050 (18)	−0.0041 (19)
C5	0.059 (2)	0.060 (2)	0.054 (2)	0.0002 (18)	0.0035 (17)	0.0006 (17)
C6	0.066 (2)	0.067 (2)	0.051 (2)	−0.0009 (19)	0.0042 (18)	−0.0020 (18)
C8	0.072 (2)	0.064 (2)	0.058 (2)	−0.007 (2)	0.0023 (19)	0.0023 (19)
C9	0.066 (2)	0.065 (2)	0.059 (2)	−0.0057 (19)	−0.0018 (18)	0.0071 (19)
C10	0.080 (3)	0.078 (3)	0.076 (3)	−0.022 (2)	−0.002 (2)	0.009 (2)
C11	0.110 (4)	0.078 (3)	0.080 (3)	−0.026 (3)	−0.009 (3)	−0.005 (2)
C12	0.103 (3)	0.074 (3)	0.071 (3)	−0.013 (3)	0.001 (3)	−0.012 (2)
C13	0.093 (3)	0.075 (3)	0.066 (2)	−0.013 (2)	0.003 (2)	−0.014 (2)
C14	0.059 (2)	0.073 (2)	0.061 (2)	−0.007 (2)	0.0077 (19)	0.009 (2)
C16	0.066 (2)	0.074 (2)	0.061 (2)	0.0077 (19)	0.0127 (19)	0.0087 (19)
C17	0.075 (3)	0.101 (3)	0.080 (3)	−0.005 (3)	0.014 (2)	−0.003 (3)
C19	0.078 (3)	0.079 (3)	0.065 (2)	0.008 (2)	0.003 (2)	0.001 (2)
C20	0.095 (3)	0.108 (4)	0.108 (3)	−0.017 (3)	0.008 (3)	−0.024 (3)
C21	0.109 (4)	0.136 (4)	0.077 (3)	0.014 (3)	0.023 (3)	−0.016 (3)
C22	0.123 (4)	0.128 (4)	0.103 (4)	0.032 (4)	−0.023 (3)	0.025 (3)
C51	0.065 (2)	0.056 (2)	0.056 (2)	−0.0021 (18)	−0.0004 (18)	−0.0003 (17)
C52	0.071 (3)	0.063 (2)	0.075 (3)	0.002 (2)	0.006 (2)	−0.008 (2)
C53	0.086 (3)	0.070 (3)	0.094 (3)	0.003 (2)	0.010 (3)	−0.018 (2)
C54	0.088 (3)	0.072 (3)	0.088 (3)	−0.004 (2)	−0.008 (3)	−0.017 (2)
C55	0.076 (3)	0.073 (3)	0.092 (3)	−0.006 (2)	−0.008 (2)	−0.014 (2)
C56	0.064 (2)	0.073 (2)	0.068 (2)	−0.004 (2)	0.0008 (19)	−0.002 (2)
C61	0.072 (3)	0.080 (3)	0.051 (2)	−0.015 (2)	0.0057 (18)	0.000 (2)
C62	0.110 (4)	0.088 (3)	0.067 (2)	−0.022 (3)	0.003 (2)	0.008 (2)
C63	0.159 (6)	0.117 (4)	0.081 (3)	−0.054 (4)	−0.001 (4)	0.020 (3)
C64	0.126 (5)	0.199 (7)	0.075 (3)	−0.074 (6)	0.013 (4)	0.007 (4)
C65	0.086 (4)	0.180 (6)	0.074 (3)	−0.032 (4)	0.015 (3)	−0.001 (4)
C66	0.065 (3)	0.125 (4)	0.062 (2)	−0.011 (3)	0.009 (2)	−0.005 (2)

Geometric parameters (Å, º) top

O18—C14	1.370 (4)	C19—C21	1.529 (6)
O18—C17	1.437 (5)	C20—H201	0.9600
N1—C6	1.330 (4)	C20—H202	0.9600
N1—N2	1.351 (4)	C20—H203	0.9600
N2—C3	1.328 (4)	C21—H211	0.9600
N4—C5	1.320 (4)	C21—H212	0.9600
N4—C3	1.351 (4)	C21—H213	0.9600
N7—C3	1.372 (4)	C22—H221	0.9600
N7—C8	1.399 (4)	C22—H222	0.9600
N7—H7	0.97 (4)	C22—H223	0.9600
N15—C14	1.264 (5)	C51—C56	1.389 (5)
N15—C16	1.482 (5)	C51—C52	1.401 (5)
C5—C6	1.415 (5)	C52—C53	1.379 (5)
C5—C51	1.490 (5)	C52—H52	0.9300
C6—C61	1.478 (5)	C53—C54	1.383 (6)
C8—C13	1.390 (5)	C53—H53	0.9300
C8—C9	1.416 (5)	C54—C55	1.382 (6)
C9—C10	1.410 (5)	C54—H54	0.9300
C9—C14	1.452 (5)	C55—C56	1.383 (5)
C10—C11	1.375 (6)	C55—H55	0.9300
C10—H10	0.9300	C56—H56	0.9300
C11—C12	1.372 (6)	C61—C66	1.377 (5)
C11—H11	0.9300	C61—C62	1.382 (5)
C12—C13	1.381 (6)	C62—C63	1.397 (7)
C12—H12	0.9300	C62—H62	0.9300
C13—H13	0.9300	C63—C64	1.378 (9)
C16—C19	1.527 (5)	C63—H63	0.9300
C16—C17	1.536 (6)	C64—C65	1.380 (8)
C16—H16	0.9800	C64—H64	0.9300
C17—H171	0.9700	C65—C66	1.381 (6)
C17—H172	0.9700	C65—H65	0.9300
C19—C22	1.528 (5)	C66—H66	0.9300
C19—C20	1.530 (6)

C14—O18—C17	106.3 (3)	C20—C19—C21	109.0 (3)
C6—N1—N2	121.1 (3)	C19—C20—H201	109.5
C3—N2—N1	116.3 (3)	C19—C20—H202	109.5
C5—N4—C3	116.8 (3)	H201—C20—H202	109.5
C3—N7—C8	131.1 (3)	C19—C20—H203	109.5
C3—N7—H7	111 (3)	H201—C20—H203	109.5
C8—N7—H7	117 (3)	H202—C20—H203	109.5
C14—N15—C16	109.1 (3)	C19—C21—H211	109.5
N2—C3—N4	126.1 (3)	C19—C21—H212	109.5
N2—C3—N7	121.5 (3)	H211—C21—H212	109.5
N4—C3—N7	112.4 (3)	C19—C21—H213	109.5
N4—C5—C6	119.6 (3)	H211—C21—H213	109.5
N4—C5—C51	114.8 (3)	H212—C21—H213	109.5
C6—C5—C51	125.6 (3)	C19—C22—H221	109.5
N1—C6—C5	119.7 (3)	C19—C22—H222	109.5
N1—C6—C61	115.2 (3)	H221—C22—H222	109.5
C5—C6—C61	125.1 (3)	C19—C22—H223	109.5
C13—C8—N7	123.4 (3)	H221—C22—H223	109.5
C13—C8—C9	119.9 (3)	H222—C22—H223	109.5
N7—C8—C9	116.7 (3)	C56—C51—C52	118.3 (3)
C10—C9—C8	117.5 (4)	C56—C51—C5	124.4 (3)
C10—C9—C14	120.0 (4)	C52—C51—C5	117.1 (3)
C8—C9—C14	122.4 (3)	C53—C52—C51	120.9 (4)
C11—C10—C9	121.7 (4)	C53—C52—H52	119.5
C11—C10—H10	119.2	C51—C52—H52	119.5
C9—C10—H10	119.2	C52—C53—C54	120.0 (4)
C10—C11—C12	119.6 (4)	C52—C53—H53	120.0
C10—C11—H11	120.2	C54—C53—H53	120.0
C12—C11—H11	120.2	C53—C54—C55	119.7 (4)
C11—C12—C13	121.0 (4)	C53—C54—H54	120.1
C11—C12—H12	119.5	C55—C54—H54	120.1
C13—C12—H12	119.5	C54—C55—C56	120.4 (4)
C12—C13—C8	120.3 (4)	C54—C55—H55	119.8
C12—C13—H13	119.9	C56—C55—H55	119.8
C8—C13—H13	119.9	C55—C56—C51	120.6 (4)
N15—C14—O18	116.6 (4)	C55—C56—H56	119.7
N15—C14—C9	128.1 (3)	C51—C56—H56	119.7
O18—C14—C9	115.3 (3)	C66—C61—C62	119.6 (4)
N15—C16—C19	113.4 (3)	C66—C61—C6	120.3 (4)
N15—C16—C17	102.4 (3)	C62—C61—C6	120.1 (4)
C19—C16—C17	117.1 (3)	C61—C62—C63	119.4 (5)
N15—C16—H16	107.8	C61—C62—H62	120.3
C19—C16—H16	107.8	C63—C62—H62	120.3
C17—C16—H16	107.8	C64—C63—C62	120.2 (6)
O18—C17—C16	105.5 (3)	C64—C63—H63	119.9
O18—C17—H171	110.6	C62—C63—H63	119.9
C16—C17—H171	110.6	C65—C64—C63	120.2 (6)
O18—C17—H172	110.6	C65—C64—H64	119.9
C16—C17—H172	110.6	C63—C64—H64	119.9
H171—C17—H172	108.8	C64—C65—C66	119.3 (6)
C16—C19—C22	111.1 (3)	C64—C65—H65	120.3
C16—C19—C20	108.4 (3)	C66—C65—H65	120.3
C22—C19—C20	110.3 (4)	C61—C66—C65	121.2 (5)
C16—C19—C21	107.7 (3)	C61—C66—H66	119.4
C22—C19—C21	110.3 (4)	C65—C66—H66	119.4

C6—N1—N2—C3	−1.4 (5)	C14—N15—C16—C19	−130.0 (4)
N1—N2—C3—N4	5.9 (6)	C14—N15—C16—C17	−2.9 (4)
N1—N2—C3—N7	−174.7 (3)	C14—O18—C17—C16	−3.5 (4)
C5—N4—C3—N2	−4.1 (5)	N15—C16—C17—O18	3.8 (4)
C5—N4—C3—N7	176.4 (3)	C19—C16—C17—O18	128.6 (4)
C8—N7—C3—N2	3.9 (6)	N15—C16—C19—C22	59.9 (5)
C8—N7—C3—N4	−176.7 (3)	C17—C16—C19—C22	−59.1 (5)
C3—N4—C5—C6	−1.9 (5)	N15—C16—C19—C20	−61.5 (4)
C3—N4—C5—C51	176.3 (3)	C17—C16—C19—C20	179.5 (3)
N2—N1—C6—C5	−4.2 (5)	N15—C16—C19—C21	−179.2 (3)
N2—N1—C6—C61	175.7 (3)	C17—C16—C19—C21	61.8 (5)
N4—C5—C6—N1	6.0 (5)	N4—C5—C51—C56	−148.3 (4)
C51—C5—C6—N1	−172.0 (3)	C6—C5—C51—C56	29.8 (6)
N4—C5—C6—C61	−174.0 (3)	N4—C5—C51—C52	26.6 (4)
C51—C5—C6—C61	8.0 (6)	C6—C5—C51—C52	−155.3 (3)
C3—N7—C8—C13	−12.4 (6)	C56—C51—C52—C53	0.0 (5)
C3—N7—C8—C9	168.3 (4)	C5—C51—C52—C53	−175.1 (3)
C13—C8—C9—C10	2.8 (5)	C51—C52—C53—C54	0.1 (6)
N7—C8—C9—C10	−177.8 (3)	C52—C53—C54—C55	−0.4 (7)
C13—C8—C9—C14	−178.7 (3)	C53—C54—C55—C56	0.5 (7)
N7—C8—C9—C14	0.7 (5)	C54—C55—C56—C51	−0.4 (6)
C8—C9—C10—C11	−1.1 (6)	C52—C51—C56—C55	0.1 (5)
C14—C9—C10—C11	−179.6 (4)	C5—C51—C56—C55	174.9 (3)
C9—C10—C11—C12	−0.7 (6)	N1—C6—C61—C66	54.0 (5)
C10—C11—C12—C13	0.8 (7)	C5—C6—C61—C66	−126.1 (4)
C11—C12—C13—C8	0.9 (6)	N1—C6—C61—C62	−125.2 (4)
N7—C8—C13—C12	177.9 (4)	C5—C6—C61—C62	54.7 (5)
C9—C8—C13—C12	−2.8 (6)	C66—C61—C62—C63	1.4 (6)
C16—N15—C14—O18	0.8 (5)	C6—C61—C62—C63	−179.4 (4)
C16—N15—C14—C9	−178.1 (3)	C61—C62—C63—C64	0.2 (8)
C17—O18—C14—N15	1.9 (4)	C62—C63—C64—C65	−0.7 (9)
C17—O18—C14—C9	−179.1 (3)	C63—C64—C65—C66	−0.4 (8)
C10—C9—C14—N15	179.6 (4)	C62—C61—C66—C65	−2.5 (6)
C8—C9—C14—N15	1.2 (6)	C6—C61—C66—C65	178.3 (4)
C10—C9—C14—O18	0.7 (5)	C64—C65—C66—C61	2.0 (7)
C8—C9—C14—O18	−177.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···N15	0.97 (4)	1.87 (5)	2.671 (4)	138 (4)
C13—H13···N2	0.93	2.31	2.919 (5)	122
C53—H53···O18ⁱ	0.93	2.54	3.250 (5)	133

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₈H₂₇N₅O
M_r	449.55
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.3306 (2), 16.9244 (6), 22.5787 (8)
V (Å³)	2419.12 (14)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.54 × 0.02 × 0.02

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.882, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	28527, 2625, 1648
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.134, 1.05
No. of reflections	2625
No. of parameters	311
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···N15	0.97 (4)	1.87 (5)	2.671 (4)	138 (4)
C13—H13···N2	0.93	2.31	2.919 (5)	122
C53—H53···O18ⁱ	0.93	2.54	3.250 (5)	133

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Castro, J., Cabaleiro, S., Perez-Lourido, P., Romero, J., Garcia-Vazquez, J. A. & Sousa, A. (2001). Polyhedron, 20, 2329–2337. Web of Science CSD CrossRef CAS Google Scholar
Coeffard, V., Müller-Bunz, H. & Guiry, P. J. (2009). Org. Biomol. Chem. 7, 1723–1734. Web of Science CSD CrossRef PubMed CAS Google Scholar
Desimoni, G., Faita, G. & Jørgensen, K. A. (2006). Chem. Rev. 106, 3561–3651. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hargaden, G. C. & Guiry, P. J. (2009). Chem. Rev. 109, 2505–2550. Web of Science CrossRef PubMed CAS Google Scholar
Lindsey, C. W. & Layton, M. E. (2004). Science of Synthesis, Houben–Weyl Methods of Molecular Transformation, Vol. 17, p. 357. Stuttgart: Georg Thieme Verlag. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o651

doi:10.1107/S1600536811005411

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-{2-[(4S)-4-tert-Butyl-4,5-di­hydro-1,3-oxazol-2-yl]phen­yl}-5,6-di­phenyl-1,2,4-triazin-3-amine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

N-{2-[(4S)-4-tert-Butyl-4,5-dihydro-1,3-oxazol-2-yl]phenyl}-5,6-diphenyl-1,2,4-triazin-3-amine