5,6-Diphenyl-3-(2-pyrid­yl)-1,2,4-triazine

Eltayeb, N.E.; Teoh, S.G.; Ng, S.-L.; Fun, H.-K.; Ibrahim, K.

doi:10.1107/S1600536807004229

5,6-Diphenyl-3-(2-pyridyl)-1,2,4-triazine

N. E. Eltayeb, S. G. Teoh, S.-L. Ng, H.-K. Fun and K. Ibrahim

In the title compound, C₂₀H₁₄N₄, the triazine ring adopts a slight twist conformation. In the crystal structure, intermolecular C—H

N interactions connect the molecules into chains along the b axis. The crystal packing is also stabilized by π–π and C—H

π interactions.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004229/fl2097sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004229/fl2097Isup2.hkl Contains datablock I

CCDC reference: 636636

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.001 Å
R factor = 0.047
wR factor = 0.131
Data-to-parameter ratio = 24.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.64 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.30
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

5,6-diphenyl-3-(2-pyridyl)-1,2,4-triazine top

Crystal data top

C₂₀H₁₄N₄	F(000) = 648
M_r = 310.35	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5288 reflections
a = 11.5830 (3) Å	θ = 2.5–32.3°
b = 11.0381 (2) Å	µ = 0.08 mm⁻¹
c = 11.9550 (3) Å	T = 100 K
β = 94.127 (1)°	Block, yellow
V = 1524.53 (6) Å³	0.64 × 0.21 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	5386 independent reflections
Radiation source: fine-focus sealed tube	4472 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 8.33 pixels mm^-1	θ_max = 32.3°, θ_min = 2.5°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→16
T_min = 0.887, T_max = 0.984	l = −17→17
38592 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0737P)² + 0.4168P] where P = (F_o² + 2F_c²)/3
5386 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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

	x	y	z	U_iso*/U_eq
N1	0.22100 (7)	0.97569 (7)	0.04307 (7)	0.01914 (16)
N2	0.30315 (7)	0.93713 (7)	−0.02143 (7)	0.01837 (16)
N3	0.14242 (7)	0.77664 (7)	0.04894 (7)	0.01676 (15)
N4	−0.03513 (8)	0.86136 (8)	0.16033 (8)	0.02276 (18)
C1	0.13972 (8)	0.89629 (8)	0.06934 (8)	0.01632 (17)
C2	0.30731 (7)	0.82014 (8)	−0.05143 (8)	0.01551 (16)
C3	0.22922 (7)	0.73615 (8)	−0.00779 (7)	0.01517 (16)
C4	0.04266 (8)	0.94385 (9)	0.13164 (8)	0.01745 (17)
C5	−0.12284 (9)	0.90026 (10)	0.21783 (10)	0.0251 (2)
H5A	−0.1774	0.8439	0.2378	0.030*
C6	−0.13695 (9)	1.02004 (10)	0.24928 (9)	0.0240 (2)
H6A	−0.1991	1.0431	0.2896	0.029*
C7	−0.05647 (9)	1.10418 (10)	0.21926 (9)	0.0241 (2)
H7A	−0.0633	1.1851	0.2394	0.029*
C8	0.03496 (9)	1.06627 (9)	0.15849 (9)	0.02139 (19)
H8A	0.0896	1.1213	0.1363	0.026*
C9	0.39533 (8)	0.78968 (8)	−0.13063 (8)	0.01603 (17)
C10	0.49966 (8)	0.85451 (9)	−0.12754 (9)	0.01981 (18)
H10A	0.5148	0.9138	−0.0732	0.024*
C11	0.58057 (9)	0.83080 (9)	−0.20493 (9)	0.0232 (2)
H11A	0.6488	0.8753	−0.2033	0.028*
C12	0.55963 (9)	0.74060 (9)	−0.28489 (9)	0.0228 (2)
H12A	0.6141	0.7243	−0.3364	0.027*
C13	0.45729 (9)	0.67495 (9)	−0.28776 (8)	0.02101 (19)
H13A	0.4437	0.6141	−0.3409	0.025*
C14	0.37493 (8)	0.69928 (9)	−0.21190 (8)	0.01820 (18)
H14A	0.3062	0.6555	−0.2151	0.022*
C15	0.23956 (7)	0.60253 (8)	−0.01411 (8)	0.01530 (16)
C16	0.34241 (8)	0.54550 (9)	0.02527 (8)	0.01760 (17)
H16A	0.4073	0.5916	0.0474	0.021*
C17	0.34750 (8)	0.41981 (9)	0.03122 (9)	0.01969 (18)
H17A	0.4154	0.3819	0.0586	0.024*
C18	0.25098 (9)	0.35064 (9)	−0.00380 (8)	0.02022 (19)
H18A	0.2546	0.2666	0.0006	0.024*
C19	0.14915 (8)	0.40664 (9)	−0.04536 (8)	0.02008 (18)
H19A	0.0855	0.3602	−0.0704	0.024*
C20	0.14303 (8)	0.53272 (8)	−0.04920 (8)	0.01833 (18)
H20A	0.0745	0.5705	−0.0752	0.022*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0189 (4)	0.0156 (3)	0.0231 (4)	0.0011 (3)	0.0024 (3)	−0.0022 (3)
N2	0.0182 (3)	0.0150 (3)	0.0220 (4)	0.0004 (3)	0.0019 (3)	−0.0016 (3)
N3	0.0175 (3)	0.0141 (3)	0.0189 (4)	0.0017 (3)	0.0025 (3)	−0.0003 (3)
N4	0.0212 (4)	0.0200 (4)	0.0279 (4)	0.0025 (3)	0.0071 (3)	0.0006 (3)
C1	0.0170 (4)	0.0151 (4)	0.0168 (4)	0.0024 (3)	0.0007 (3)	−0.0008 (3)
C2	0.0152 (4)	0.0145 (4)	0.0167 (4)	0.0002 (3)	0.0009 (3)	0.0001 (3)
C3	0.0150 (3)	0.0138 (4)	0.0165 (4)	0.0010 (3)	0.0002 (3)	−0.0001 (3)
C4	0.0186 (4)	0.0169 (4)	0.0168 (4)	0.0034 (3)	0.0010 (3)	−0.0011 (3)
C5	0.0223 (4)	0.0252 (5)	0.0287 (5)	0.0029 (4)	0.0082 (4)	0.0010 (4)
C6	0.0237 (4)	0.0294 (5)	0.0190 (4)	0.0081 (4)	0.0030 (4)	−0.0039 (4)
C7	0.0266 (5)	0.0225 (5)	0.0230 (5)	0.0064 (4)	0.0012 (4)	−0.0083 (4)
C8	0.0232 (4)	0.0185 (4)	0.0224 (4)	0.0016 (3)	0.0012 (4)	−0.0044 (3)
C9	0.0169 (4)	0.0140 (4)	0.0173 (4)	0.0004 (3)	0.0020 (3)	0.0017 (3)
C10	0.0203 (4)	0.0144 (4)	0.0250 (4)	−0.0022 (3)	0.0042 (3)	−0.0005 (3)
C11	0.0204 (4)	0.0197 (4)	0.0305 (5)	−0.0017 (3)	0.0078 (4)	0.0030 (4)
C12	0.0243 (4)	0.0235 (5)	0.0215 (4)	0.0024 (4)	0.0078 (4)	0.0039 (4)
C13	0.0262 (4)	0.0206 (4)	0.0164 (4)	0.0012 (3)	0.0025 (3)	0.0000 (3)
C14	0.0191 (4)	0.0183 (4)	0.0172 (4)	−0.0009 (3)	0.0012 (3)	0.0005 (3)
C15	0.0160 (4)	0.0134 (4)	0.0169 (4)	0.0008 (3)	0.0039 (3)	0.0005 (3)
C16	0.0153 (4)	0.0167 (4)	0.0211 (4)	0.0005 (3)	0.0035 (3)	0.0018 (3)
C17	0.0185 (4)	0.0167 (4)	0.0243 (4)	0.0032 (3)	0.0053 (3)	0.0029 (3)
C18	0.0247 (4)	0.0138 (4)	0.0229 (4)	0.0008 (3)	0.0071 (4)	−0.0005 (3)
C19	0.0213 (4)	0.0169 (4)	0.0222 (4)	−0.0029 (3)	0.0028 (3)	−0.0027 (3)
C20	0.0171 (4)	0.0163 (4)	0.0216 (4)	0.0000 (3)	0.0014 (3)	−0.0010 (3)

Geometric parameters (Å, º) top

N1—N2	1.3368 (12)	C10—C11	1.3884 (14)
N1—C1	1.3400 (12)	C10—H10A	0.9300
N2—C2	1.3420 (12)	C11—C12	1.3893 (15)
N3—C3	1.3299 (11)	C11—H11A	0.9300
N3—C1	1.3439 (12)	C12—C13	1.3878 (14)
N4—C5	1.3378 (13)	C12—H12A	0.9300
N4—C4	1.3428 (13)	C13—C14	1.3889 (13)
C1—C4	1.4883 (13)	C13—H13A	0.9300
C2—C3	1.4206 (12)	C14—H14A	0.9300
C2—C9	1.4792 (13)	C15—C20	1.3973 (13)
C3—C15	1.4820 (12)	C15—C16	1.3988 (12)
C4—C8	1.3932 (13)	C16—C17	1.3903 (13)
C5—C6	1.3874 (15)	C16—H16A	0.9300
C5—H5A	0.9300	C17—C18	1.3932 (14)
C6—C7	1.3815 (16)	C17—H17A	0.9300
C6—H6A	0.9300	C18—C19	1.3913 (14)
C7—C8	1.3912 (14)	C18—H18A	0.9300
C7—H7A	0.9300	C19—C20	1.3941 (13)
C8—H8A	0.9300	C19—H19A	0.9300
C9—C14	1.4009 (13)	C20—H20A	0.9300
C9—C10	1.4026 (13)

N2—N1—C1	117.92 (8)	C11—C10—H10A	119.7
N1—N2—C2	120.09 (8)	C9—C10—H10A	119.7
C3—N3—C1	116.82 (8)	C10—C11—C12	120.05 (9)
C5—N4—C4	117.51 (9)	C10—C11—H11A	120.0
N1—C1—N3	125.06 (8)	C12—C11—H11A	120.0
N1—C1—C4	117.09 (8)	C13—C12—C11	119.85 (9)
N3—C1—C4	117.76 (8)	C13—C12—H12A	120.1
N2—C2—C3	119.59 (8)	C11—C12—H12A	120.1
N2—C2—C9	115.43 (8)	C12—C13—C14	120.56 (9)
C3—C2—C9	124.97 (8)	C12—C13—H13A	119.7
N3—C3—C2	119.52 (8)	C14—C13—H13A	119.7
N3—C3—C15	115.29 (8)	C13—C14—C9	120.07 (9)
C2—C3—C15	125.09 (8)	C13—C14—H14A	120.0
N4—C4—C8	122.93 (9)	C9—C14—H14A	120.0
N4—C4—C1	115.70 (8)	C20—C15—C16	119.78 (8)
C8—C4—C1	121.37 (9)	C20—C15—C3	119.88 (8)
N4—C5—C6	123.63 (10)	C16—C15—C3	120.04 (8)
N4—C5—H5A	118.2	C17—C16—C15	119.89 (8)
C6—C5—H5A	118.2	C17—C16—H16A	120.1
C7—C6—C5	118.39 (9)	C15—C16—H16A	120.1
C7—C6—H6A	120.8	C16—C17—C18	120.09 (9)
C5—C6—H6A	120.8	C16—C17—H17A	120.0
C6—C7—C8	119.13 (9)	C18—C17—H17A	120.0
C6—C7—H7A	120.4	C19—C18—C17	120.35 (9)
C8—C7—H7A	120.4	C19—C18—H18A	119.8
C7—C8—C4	118.41 (10)	C17—C18—H18A	119.8
C7—C8—H8A	120.8	C18—C19—C20	119.68 (9)
C4—C8—H8A	120.8	C18—C19—H19A	120.2
C14—C9—C10	118.93 (8)	C20—C19—H19A	120.2
C14—C9—C2	121.08 (8)	C19—C20—C15	120.19 (8)
C10—C9—C2	119.96 (8)	C19—C20—H20A	119.9
C11—C10—C9	120.52 (9)	C15—C20—H20A	119.9

C1—N1—N2—C2	−4.61 (13)	N2—C2—C9—C14	−146.04 (9)
N2—N1—C1—N3	9.52 (14)	C3—C2—C9—C14	33.36 (14)
N2—N1—C1—C4	−174.14 (8)	N2—C2—C9—C10	31.80 (12)
C3—N3—C1—N1	−4.32 (14)	C3—C2—C9—C10	−148.79 (9)
C3—N3—C1—C4	179.36 (8)	C14—C9—C10—C11	1.04 (14)
N1—N2—C2—C3	−4.46 (13)	C2—C9—C10—C11	−176.85 (9)
N1—N2—C2—C9	174.98 (8)	C9—C10—C11—C12	−1.31 (15)
C1—N3—C3—C2	−5.27 (12)	C10—C11—C12—C13	0.51 (16)
C1—N3—C3—C15	171.27 (8)	C11—C12—C13—C14	0.55 (15)
N2—C2—C3—N3	9.67 (13)	C12—C13—C14—C9	−0.81 (15)
C9—C2—C3—N3	−169.72 (8)	C10—C9—C14—C13	0.02 (14)
N2—C2—C3—C15	−166.51 (9)	C2—C9—C14—C13	177.88 (8)
C9—C2—C3—C15	14.11 (14)	N3—C3—C15—C20	51.09 (12)
C5—N4—C4—C8	−0.42 (15)	C2—C3—C15—C20	−132.59 (10)
C5—N4—C4—C1	179.08 (9)	N3—C3—C15—C16	−122.67 (9)
N1—C1—C4—N4	−177.66 (9)	C2—C3—C15—C16	53.64 (13)
N3—C1—C4—N4	−1.04 (13)	C20—C15—C16—C17	−1.16 (14)
N1—C1—C4—C8	1.86 (13)	C3—C15—C16—C17	172.61 (9)
N3—C1—C4—C8	178.48 (9)	C15—C16—C17—C18	1.12 (15)
C4—N4—C5—C6	−0.27 (16)	C16—C17—C18—C19	0.28 (15)
N4—C5—C6—C7	0.32 (17)	C17—C18—C19—C20	−1.63 (15)
C5—C6—C7—C8	0.31 (16)	C18—C19—C20—C15	1.58 (15)
C6—C7—C8—C4	−0.95 (15)	C16—C15—C20—C19	−0.19 (14)
N4—C4—C8—C7	1.04 (15)	C3—C15—C20—C19	−173.97 (9)
C1—C4—C8—C7	−178.44 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···N4ⁱ	0.93	2.52	3.322 (1)	145
C6—H6A···Cg4ⁱ	0.93	2.82	3.470 (1)	128
C13—H13A···Cg1ⁱⁱ	0.93	3.00	3.487 (1)	115
C14—H14A···Cg1ⁱⁱ	0.93	3.32	3.661 (1)	104
C17—H17A···Cg3ⁱⁱⁱ	0.93	2.65	3.478 (1)	149
C20—H20A···Cg2ⁱⁱ	0.93	3.10	3.685 (1)	122

Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) x, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

5,6-Diphenyl-3-(2-pyrid­yl)-1,2,4-triazine

Supporting information

Key indicators

checkCIF/PLATON results

5,6-Diphenyl-3-(2-pyridyl)-1,2,4-triazine