5-(N,N-Diethyl­amino)-4,6-diphenyl-1,2,3-triazine

In the title compound, C₁₉H₂₀N₄, the dihedral angles formed by the planes of the triazine ring and the two phenyl substituents are 51.54 (1) and 49.27 (1)°. The phenyl rings form a dihedral angle of 80.81 (1)°. All bond lengths and angles are normal. The structure is stabilized by van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.035
• wR factor = 0.087
• Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N4     -   C8      ..       5.26 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C6      ..       6.22 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C5      ..       6.61 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       6.17 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C15     ..       5.20 su

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           27.44
           From the CIF: _reflns_number_total               1894
           Count of symmetry unique reflns         1894
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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

---

Computing details

Data collection: DARCH Package (reference?); cell refinement: DARCH Package; data reduction: DARCH Package; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97.

5-(N,N-Diethylamino)-4,6-diphenyl-1,2,3-triazine

Crystal data

C19H20N4	F(000) = 648
Mr = 304.39	Dx = 1.263 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2c -2ac	Cell parameters from 20 reflections
a = 12.535 (3) Å	θ = 10–16°
b = 7.856 (2) Å	µ = 0.08 mm^−1
c = 16.253 (3) Å	T = 293 K
V = 1600.5 (6) Å^3	Needle, clear pale yellow
Z = 4	0.50 × 0.06 × 0.02 mm

Data collection

DARCH-1 diffractometer	1563 reflections with I > 2σ(I)
Radiation source: BSW x-ray tube	Rint = 0.020
Graphite monochromator	θmax = 27.4°, θmin = 2.5°
ω–2θ scans	h = 0→16
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart, 1983)	k = 0→10
Tmin = 0.957, Tmax = 0.998	l = −10→20
3080 measured reflections	3 standard reflections every 100 reflections
1894 independent reflections	intensity decay: 2.3%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.088	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0374P)^2] where P = (Fo^2 + 2Fc^2)/3
1895 reflections	(Δ/σ)max = 0.006
213 parameters	Δρmax = 0.11 e Å^−3
1 restraint	Δρmin = −0.14 e Å^−3

Special details

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
N1	0.59182 (17)	0.0192 (2)	0.00777 (13)	0.0810 (5)
N2	0.66218 (18)	0.0129 (3)	−0.05176 (15)	0.0885 (6)
N3	0.73609 (18)	0.1380 (3)	−0.05968 (14)	0.0887 (5)
N4	0.67108 (14)	0.4116 (2)	0.11396 (12)	0.0761 (5)
C1	0.5380 (2)	0.1223 (3)	0.21012 (14)	0.0816 (6)
H1	0.6071	0.1496	0.2262	0.091 (2)*
C2	0.4612 (2)	0.0825 (3)	0.26871 (17)	0.0898 (7)
H2	0.4798	0.0832	0.3241	0.091 (2)*
C3	0.3605 (2)	0.0430 (3)	0.24700 (19)	0.0933 (7)
H3	0.3101	0.0179	0.2872	0.091 (2)*
C4	0.3328 (2)	0.0398 (3)	0.16653 (18)	0.0896 (7)
H4	0.2634	0.0129	0.1511	0.091 (2)*
C5	0.40901 (18)	0.0770 (3)	0.10711 (17)	0.0809 (6)
H5	0.3900	0.0717	0.0519	0.091 (2)*
C6	0.51085 (18)	0.1210 (3)	0.12755 (16)	0.0774 (6)
C7	0.59099 (17)	0.1478 (3)	0.06241 (14)	0.0706 (5)
C8	0.66612 (16)	0.2824 (3)	0.05852 (13)	0.0700 (5)
C9	0.73699 (16)	0.2707 (3)	−0.00903 (14)	0.0704 (5)
C10	0.81407 (17)	0.4004 (3)	−0.03567 (14)	0.0740 (5)
C11	0.9153 (2)	0.3544 (4)	−0.06073 (17)	0.0891 (7)
H11	0.9372	0.2422	−0.0539	0.091 (2)*
C12	0.9838 (2)	0.4682 (5)	−0.09500 (18)	0.1002 (9)
H12	1.0512	0.4329	−0.1118	0.091 (2)*
C13	0.9543 (2)	0.6324 (4)	−0.10476 (19)	0.0940 (7)
H13	1.0012	0.7104	−0.1281	0.091 (2)*
C14	0.8530 (2)	0.6841 (4)	−0.07967 (16)	0.0924 (7)
H14	0.8316	0.7966	−0.0862	0.091 (2)*
C15	0.78562 (19)	0.5672 (3)	−0.04542 (15)	0.0794 (6)
H15	0.7183	0.6022	−0.0282	0.091 (2)*
C16	0.57540 (17)	0.4903 (3)	0.14752 (19)	0.0774 (6)
H16A	0.5668	0.4543	0.2042	0.072 (3)*
H16B	0.5139	0.4500	0.1169	0.072 (3)*
C17	0.77252 (17)	0.4671 (3)	0.14785 (17)	0.0773 (6)
H17A	0.8290	0.4021	0.1218	0.072 (3)*
H17B	0.7831	0.5857	0.1333	0.072 (3)*
C18	0.5775 (2)	0.6783 (3)	0.1446 (2)	0.0992 (8)
H18A	0.6394	0.7192	0.1732	0.107 (4)*
H18B	0.5144	0.7226	0.1703	0.107 (4)*
H18C	0.5801	0.7152	0.0883	0.107 (4)*
C19	0.7836 (2)	0.4505 (5)	0.23671 (19)	0.1035 (9)
H19A	0.7336	0.5244	0.2635	0.107 (4)*
H19B	0.8548	0.4812	0.2526	0.107 (4)*
H19C	0.7698	0.3348	0.2525	0.107 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0980 (13)	0.0732 (11)	0.0716 (12)	−0.0083 (9)	0.0038 (10)	−0.0026 (9)
N2	0.0922 (15)	0.0815 (12)	0.0719 (12)	−0.0058 (11)	0.0047 (12)	−0.0078 (10)
N3	0.0907 (13)	0.0771 (12)	0.0782 (13)	−0.0063 (11)	−0.0001 (10)	−0.0082 (11)
N4	0.0759 (10)	0.0794 (10)	0.0730 (12)	0.0009 (8)	−0.0014 (9)	−0.0038 (9)
C1	0.0862 (16)	0.0812 (14)	0.0694 (13)	−0.0105 (11)	−0.0051 (12)	0.0069 (11)
C2	0.1099 (19)	0.0897 (16)	0.0698 (15)	−0.0139 (14)	−0.0016 (13)	−0.0002 (13)
C3	0.0941 (18)	0.0821 (15)	0.083 (2)	−0.0160 (14)	0.0096 (16)	0.0040 (13)
C4	0.0875 (14)	0.0892 (15)	0.0798 (2)	−0.0088 (11)	−0.0011 (14)	−0.0086 (14)
C5	0.0801 (13)	0.0835 (14)	0.0753 (15)	0.0043 (11)	0.0053 (11)	0.0016 (12)
C6	0.0840 (13)	0.0765 (10)	0.0757 (16)	0.0063 (10)	0.0075 (12)	0.0045 (11)
C7	0.0744 (12)	0.0748 (11)	0.0625 (12)	0.0085 (9)	−0.0067 (9)	0.0018 (10)
C8	0.0727 (12)	0.0697 (11)	0.0676 (13)	0.0095 (9)	−0.0033 (10)	−0.0049 (10)
C9	0.0833 (12)	0.0677 (11)	0.0702 (13)	−0.0035 (9)	−0.0009 (10)	−0.0067 (10)
C10	0.0803 (12)	0.0844 (13)	0.0724 (13)	−0.0018 (10)	0.0050 (10)	−0.0018 (10)
C11	0.0903 (16)	0.0950 (16)	0.0820 (16)	−0.0093 (13)	0.0058 (12)	−0.0072 (13)
C12	0.0905 (12)	0.0951 (3)	0.0843 (19)	−0.0107 (15)	0.0055 (12)	−0.0024 (17)
C13	0.1012 (19)	0.0966 (18)	0.0842 (17)	−0.0174 (14)	0.0009 (14)	0.0062 (14)
C14	0.1143 (19)	0.0897 (15)	0.0732 (15)	−0.0100 (14)	0.0084 (14)	−0.0047 (12)
C15	0.0769 (13)	0.0967 (15)	0.0644 (13)	−0.0011 (11)	0.0057 (11)	0.0017 (12)
C16	0.0694 (11)	0.0812 (12)	0.0816 (15)	−0.0013 (9)	0.0081 (11)	0.0034 (11)
C17	0.0746 (12)	0.0766 (12)	0.0806 (16)	−0.0035 (9)	−0.0064 (11)	−0.0056 (11)
C18	0.0956 (16)	0.0722 (13)	0.130 (2)	0.0086 (11)	−0.0009 (17)	−0.0041 (15)
C19	0.0866 (16)	0.138 (2)	0.0857 (19)	0.0025 (15)	−0.0099 (14)	−0.0179 (17)

Geometric parameters (Å, º)

N1—N2	1.310 (3)	C10—C11	1.381 (3)
N1—C7	1.345 (3)	C11—C12	1.359 (4)
N2—N3	1.357 (3)	C11—H11	0.9300
N3—C9	1.329 (3)	C12—C13	1.351 (4)
N4—C8	1.359 (3)	C12—H12	0.9300
N4—C17	1.453 (3)	C13—C14	1.394 (4)
N4—C16	1.455 (3)	C13—H13	0.9300
C1—C6	1.384 (3)	C14—C15	1.366 (4)
C1—C2	1.389 (4)	C14—H14	0.9300
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.348 (4)	C16—C18	1.478 (3)
C2—H2	0.9300	C16—H16A	0.9700
C3—C4	1.353 (4)	C16—H16B	0.9700
C3—H3	0.9300	C17—C19	1.457 (4)
C4—C5	1.389 (4)	C17—H17A	0.9700
C4—H4	0.9300	C17—H17B	0.9700
C5—C6	1.364 (3)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—C7	1.475 (3)	C18—H18C	0.9600
C7—C8	1.417 (3)	C19—H19A	0.9600
C8—C9	1.415 (3)	C19—H19B	0.9600
C9—C10	1.470 (3)	C19—H19C	0.9600
C10—C15	1.367 (3)
N2—N1—C7	121.39 (19)	C10—C11—H11	119.0
N1—N2—N3	120.17 (19)	C13—C12—C11	120.2 (3)
C9—N3—N2	121.0 (2)	C13—C12—H12	119.9
C8—N4—C17	121.06 (18)	C11—C12—H12	119.9
C8—N4—C16	121.89 (18)	C12—C13—C14	119.6 (3)
C17—N4—C16	116.84 (19)	C12—C13—H13	120.2
C6—C1—C2	119.5 (2)	C14—C13—H13	120.2
C6—C1—H1	120.2	C15—C14—C13	119.1 (3)
C2—C1—H1	120.2	C15—C14—H14	120.4
C3—C2—C1	121.4 (3)	C13—C14—H14	120.4
C3—C2—H2	119.3	C14—C15—C10	122.0 (2)
C1—C2—H2	119.3	C14—C15—H15	119.0
C2—C3—C4	119.8 (3)	C10—C15—H15	119.0
C2—C3—H3	120.1	N4—C16—C18	113.4 (2)
C4—C3—H3	120.1	N4—C16—H16A	108.9
C3—C4—C5	119.5 (3)	C18—C16—H16A	108.9
C3—C4—H4	120.3	N4—C16—H16B	108.9
C5—C4—H4	120.3	C18—C16—H16B	108.9
C6—C5—C4	121.8 (3)	H16A—C16—H16B	107.7
C6—C5—H5	119.1	C19—C17—N4	115.6 (2)
C4—C5—H5	119.1	C19—C17—H17A	108.4
C5—C6—C1	117.9 (2)	N4—C17—H17A	108.4
C5—C6—C7	119.9 (2)	C19—C17—H17B	108.4
C1—C6—C7	121.9 (2)	N4—C17—H17B	108.4
N1—C7—C8	121.7 (2)	H17A—C17—H17B	107.4
N1—C7—C6	111.83 (19)	C16—C18—H18A	109.5
C8—C7—C6	126.2 (2)	C16—C18—H18B	109.5
N4—C8—C9	122.27 (19)	H18A—C18—H18B	109.5
N4—C8—C7	123.93 (19)	C16—C18—H18C	109.5
C9—C8—C7	113.80 (19)	H18A—C18—H18C	109.5
N3—C9—C8	121.7 (2)	H18B—C18—H18C	109.5
N3—C9—C10	111.5 (2)	C17—C19—H19A	109.5
C8—C9—C10	126.62 (19)	C17—C19—H19B	109.5
C15—C10—C11	117.2 (2)	H19A—C19—H19B	109.5
C15—C10—C9	121.8 (2)	C17—C19—H19C	109.5
C11—C10—C9	120.6 (2)	H19A—C19—H19C	109.5
C12—C11—C10	122.0 (3)	H19B—C19—H19C	109.5
C12—C11—H11	119.0
C7—N1—N2—N3	−0.3 (4)	C6—C7—C8—C9	176.9 (2)
N1—N2—N3—C9	−1.8 (4)	N2—N3—C9—C8	4.3 (3)
C6—C1—C2—C3	−0.2 (4)	N2—N3—C9—C10	−172.4 (2)
C1—C2—C3—C4	0.7 (4)	N4—C8—C9—N3	175.4 (2)
C2—C3—C4—C5	0.2 (4)	C7—C8—C9—N3	−4.5 (3)
C3—C4—C5—C6	−1.7 (4)	N4—C8—C9—C10	−8.4 (3)
C4—C5—C6—C1	2.1 (4)	C7—C8—C9—C10	171.7 (2)
C4—C5—C6—C7	175.8 (2)	N3—C9—C10—C15	127.8 (2)
C2—C1—C6—C5	−1.2 (3)	C8—C9—C10—C15	−48.7 (3)
C2—C1—C6—C7	−174.7 (2)	N3—C9—C10—C11	−44.8 (3)
N2—N1—C7—C8	−0.2 (3)	C8—C9—C10—C11	138.7 (2)
N2—N1—C7—C6	−175.3 (2)	C15—C10—C11—C12	−1.1 (4)
C5—C6—C7—N1	−48.8 (3)	C9—C10—C11—C12	171.9 (3)
C1—C6—C7—N1	124.5 (2)	C10—C11—C12—C13	0.7 (5)
C5—C6—C7—C8	136.3 (2)	C11—C12—C13—C14	−0.2 (5)
C1—C6—C7—C8	−50.3 (3)	C12—C13—C14—C15	0.2 (4)
C17—N4—C8—C9	−45.1 (3)	C13—C14—C15—C10	−0.6 (4)
C16—N4—C8—C9	140.4 (2)	C11—C10—C15—C14	1.1 (4)
C17—N4—C8—C7	134.8 (2)	C9—C10—C15—C14	−171.8 (2)
C16—N4—C8—C7	−39.7 (3)	C8—N4—C16—C18	−131.5 (3)
N1—C7—C8—N4	−177.5 (2)	C17—N4—C16—C18	53.8 (3)
C6—C7—C8—N4	−3.1 (3)	C8—N4—C17—C19	−118.7 (3)
N1—C7—C8—C9	2.5 (3)	C16—N4—C17—C19	56.0 (3)