1-Benzoyl-3,6-diphenyl-1,4-dihydro-1,2,4,5-tetra-zine.

In the title compound, C(21)H(16)N(4)O, the central tetra-zine ring adopts an unsymmetrical boat conformation with the two N atoms as the bow and stern. The crystal packing is stabilized by inter-molecular N-H-O hydrogen bonds.

Related literature

For related structures, see: Xu et al. (2010 ▶); Hu et al. (2004 ▶); Rao et al. (2006 ▶). For applications of 1,2,4,5-tetra­zine derivatives, see: Sauer et al. (1996 ▶).

Experimental

Crystal data

C21H16N4O

M = 340.38

Orthorhombic,

a = 7.1100 (19) Å

b = 12.115 (3) Å

c = 19.884 (6) Å

V = 1712.7 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 93 K

0.43 × 0.27 × 0.27 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer

13708 measured reflections

2254 independent reflections

2128 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.085

S = 1.00

2254 reflections

239 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810038067/bq2236sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038067/bq2236Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H16N4O	F(000) = 712
Mr = 340.38	Dx = 1.320 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2254 reflections
a = 7.1100 (19) Å	θ = 3.4–27.5°
b = 12.115 (3) Å	µ = 0.09 mm−1
c = 19.884 (6) Å	T = 93 K
V = 1712.7 (8) Å3	Column, yellow
Z = 4	0.43 × 0.27 × 0.27 mm

Rigaku AFC10/Saturn724+ diffractometer	2128 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.032
graphite	θmax = 27.5°, θmin = 3.0°
Detector resolution: 28.5714 pixels mm-1	h = −9→9
φ and ω scans	k = −15→14
13708 measured reflections	l = −24→25
2254 independent reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0577P)2 + 0.196P] where P = (Fo2 + 2Fc2)/3
2254 reflections	(Δ/σ)max = 0.001
239 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
O1	0.41566 (18)	0.55133 (9)	0.57735 (6)	0.0169 (3)
N1	0.1772 (2)	0.56642 (12)	0.50300 (7)	0.0160 (3)
N2	0.1136 (2)	0.55047 (12)	0.43512 (7)	0.0166 (3)
N4	0.0860 (2)	0.74205 (12)	0.44154 (7)	0.0166 (3)
N5	0.0366 (2)	0.74009 (12)	0.50949 (7)	0.0171 (3)
C3	0.0818 (2)	0.64438 (14)	0.40646 (8)	0.0155 (3)
C6	0.0824 (2)	0.65060 (13)	0.53963 (8)	0.0153 (3)
C7	0.0230 (2)	0.62957 (14)	0.60945 (8)	0.0166 (4)
C8	0.0051 (3)	0.52210 (15)	0.63299 (9)	0.0203 (4)
H8	0.0357	0.4620	0.6043	0.024*
C9	−0.0570 (3)	0.50186 (15)	0.69807 (9)	0.0237 (4)
H9	−0.0689	0.4281	0.7137	0.028*
C10	−0.1015 (3)	0.58866 (16)	0.74016 (9)	0.0234 (4)
H10	−0.1438	0.5747	0.7847	0.028*
C11	−0.0842 (3)	0.69637 (16)	0.71726 (9)	0.0230 (4)
H11	−0.1144	0.7561	0.7463	0.028*
C12	−0.0230 (3)	0.71750 (15)	0.65229 (9)	0.0197 (4)
H12	−0.0124	0.7914	0.6368	0.024*
C13	0.0390 (2)	0.64618 (14)	0.33354 (8)	0.0163 (3)
C14	0.1052 (3)	0.55940 (15)	0.29386 (9)	0.0203 (4)
H14	0.1729	0.5004	0.3140	0.024*
C15	0.0725 (3)	0.55907 (16)	0.22504 (9)	0.0225 (4)
H15	0.1169	0.4996	0.1982	0.027*
C16	−0.0250 (3)	0.64547 (16)	0.19537 (9)	0.0217 (4)
H16	−0.0468	0.6453	0.1482	0.026*
C17	−0.0907 (3)	0.73210 (16)	0.23452 (9)	0.0234 (4)
H17	−0.1570	0.7914	0.2141	0.028*
C18	−0.0594 (3)	0.73225 (15)	0.30386 (9)	0.0200 (4)
H18	−0.1054	0.7913	0.3307	0.024*
C19	0.3449 (2)	0.52356 (13)	0.52322 (8)	0.0141 (3)
C20	0.4384 (2)	0.44072 (14)	0.47866 (8)	0.0153 (3)
C21	0.6317 (3)	0.45175 (15)	0.46805 (9)	0.0197 (4)
H21	0.6976	0.5123	0.4872	0.024*
C22	0.7276 (3)	0.37442 (15)	0.42963 (10)	0.0242 (4)
H22	0.8583	0.3833	0.4211	0.029*
C23	0.6319 (3)	0.28419 (16)	0.40369 (9)	0.0221 (4)
H23	0.6978	0.2302	0.3782	0.027*
C24	0.4404 (3)	0.27244 (15)	0.41477 (8)	0.0207 (4)
H24	0.3757	0.2104	0.3969	0.025*
C25	0.3424 (3)	0.35102 (14)	0.45181 (9)	0.0187 (4)
H25	0.2108	0.3435	0.4587	0.022*
H4N	0.048 (3)	0.8053 (17)	0.4209 (10)	0.020 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0209 (6)	0.0155 (6)	0.0144 (5)	−0.0013 (5)	−0.0018 (5)	0.0010 (4)
N1	0.0183 (7)	0.0151 (7)	0.0145 (6)	0.0020 (6)	−0.0008 (6)	−0.0025 (6)
N2	0.0181 (7)	0.0185 (7)	0.0132 (6)	0.0027 (6)	−0.0010 (6)	−0.0031 (6)
N4	0.0226 (7)	0.0142 (7)	0.0129 (6)	0.0022 (6)	0.0006 (6)	−0.0005 (5)
N5	0.0198 (7)	0.0172 (7)	0.0145 (7)	0.0004 (6)	0.0018 (6)	−0.0028 (5)
C3	0.0140 (8)	0.0153 (8)	0.0171 (7)	0.0000 (7)	0.0003 (6)	−0.0029 (6)
C6	0.0164 (8)	0.0126 (8)	0.0170 (8)	0.0012 (7)	−0.0021 (6)	−0.0039 (6)
C7	0.0140 (8)	0.0185 (9)	0.0172 (8)	−0.0001 (7)	−0.0017 (6)	−0.0020 (7)
C8	0.0201 (9)	0.0174 (8)	0.0233 (8)	−0.0022 (7)	0.0023 (7)	−0.0025 (7)
C9	0.0226 (9)	0.0227 (10)	0.0256 (9)	−0.0035 (8)	0.0032 (8)	0.0035 (7)
C10	0.0214 (9)	0.0323 (10)	0.0165 (8)	−0.0013 (8)	0.0031 (7)	0.0020 (7)
C11	0.0239 (9)	0.0273 (10)	0.0179 (8)	0.0037 (8)	0.0005 (7)	−0.0052 (7)
C12	0.0231 (9)	0.0179 (8)	0.0181 (8)	0.0039 (8)	−0.0008 (7)	−0.0019 (7)
C13	0.0141 (8)	0.0184 (8)	0.0162 (7)	−0.0025 (7)	0.0005 (6)	−0.0009 (6)
C14	0.0222 (9)	0.0180 (9)	0.0206 (8)	0.0016 (7)	−0.0017 (7)	−0.0019 (7)
C15	0.0240 (9)	0.0241 (9)	0.0195 (8)	−0.0004 (9)	0.0015 (7)	−0.0060 (7)
C16	0.0200 (8)	0.0303 (10)	0.0148 (7)	−0.0042 (8)	−0.0006 (7)	−0.0006 (7)
C17	0.0235 (9)	0.0256 (10)	0.0210 (8)	0.0022 (8)	−0.0044 (7)	0.0016 (7)
C18	0.0197 (9)	0.0213 (9)	0.0191 (8)	0.0023 (8)	−0.0005 (7)	−0.0023 (7)
C19	0.0173 (8)	0.0108 (7)	0.0143 (7)	−0.0013 (7)	0.0017 (6)	0.0027 (6)
C20	0.0197 (8)	0.0141 (8)	0.0121 (7)	0.0015 (7)	−0.0004 (6)	0.0017 (6)
C21	0.0189 (9)	0.0183 (9)	0.0219 (8)	−0.0006 (7)	−0.0013 (7)	0.0003 (7)
C22	0.0180 (9)	0.0276 (10)	0.0269 (9)	0.0035 (8)	0.0017 (7)	−0.0001 (8)
C23	0.0254 (10)	0.0218 (9)	0.0192 (8)	0.0093 (8)	0.0009 (7)	−0.0007 (7)
C24	0.0262 (9)	0.0162 (8)	0.0197 (8)	0.0018 (8)	−0.0054 (7)	−0.0025 (7)
C25	0.0191 (8)	0.0162 (8)	0.0208 (8)	0.0008 (8)	−0.0011 (7)	−0.0008 (7)

O1—C19	1.235 (2)	C13—C14	1.396 (2)
N1—C19	1.361 (2)	C14—C15	1.388 (2)
N1—C6	1.423 (2)	C14—H14	0.9500
N1—N2	1.4363 (19)	C15—C16	1.387 (3)
N2—C3	1.292 (2)	C15—H15	0.9500
N4—C3	1.374 (2)	C16—C17	1.388 (3)
N4—N5	1.3961 (19)	C16—H16	0.9500
N4—H4N	0.91 (2)	C17—C18	1.397 (2)
N5—C6	1.281 (2)	C17—H17	0.9500
C3—C13	1.482 (2)	C18—H18	0.9500
C6—C7	1.473 (2)	C19—C20	1.495 (2)
C7—C8	1.389 (3)	C20—C25	1.390 (2)
C7—C12	1.403 (2)	C20—C21	1.396 (2)
C8—C9	1.389 (3)	C21—C22	1.388 (3)
C8—H8	0.9500	C21—H21	0.9500
C9—C10	1.381 (3)	C22—C23	1.387 (3)
C9—H9	0.9500	C22—H22	0.9500
C10—C11	1.388 (3)	C23—C24	1.387 (3)
C10—H10	0.9500	C23—H23	0.9500
C11—C12	1.387 (2)	C24—C25	1.391 (3)
C11—H11	0.9500	C24—H24	0.9500
C12—H12	0.9500	C25—H25	0.9500
C13—C18	1.387 (2)
C19—N1—C6	122.48 (14)	C15—C14—H14	119.9
C19—N1—N2	120.12 (13)	C13—C14—H14	119.9
C6—N1—N2	115.36 (14)	C16—C15—C14	120.06 (17)
C3—N2—N1	110.55 (13)	C16—C15—H15	120.0
C3—N4—N5	118.11 (14)	C14—C15—H15	120.0
C3—N4—H4N	119.3 (13)	C15—C16—C17	120.02 (16)
N5—N4—H4N	112.0 (13)	C15—C16—H16	120.0
C6—N5—N4	113.79 (14)	C17—C16—H16	120.0
N2—C3—N4	122.04 (14)	C16—C17—C18	120.08 (18)
N2—C3—C13	118.71 (15)	C16—C17—H17	120.0
N4—C3—C13	119.25 (15)	C18—C17—H17	120.0
N5—C6—N1	119.17 (15)	C13—C18—C17	119.95 (17)
N5—C6—C7	120.97 (15)	C13—C18—H18	120.0
N1—C6—C7	119.61 (15)	C17—C18—H18	120.0
C8—C7—C12	119.05 (16)	O1—C19—N1	120.69 (15)
C8—C7—C6	120.39 (15)	O1—C19—C20	121.22 (15)
C12—C7—C6	120.52 (15)	N1—C19—C20	118.08 (14)
C9—C8—C7	120.56 (17)	C25—C20—C21	120.00 (17)
C9—C8—H8	119.7	C25—C20—C19	122.27 (16)
C7—C8—H8	119.7	C21—C20—C19	117.59 (16)
C10—C9—C8	120.20 (17)	C22—C21—C20	120.15 (18)
C10—C9—H9	119.9	C22—C21—H21	119.9
C8—C9—H9	119.9	C20—C21—H21	119.9
C9—C10—C11	119.80 (16)	C23—C22—C21	119.68 (18)
C9—C10—H10	120.1	C23—C22—H22	120.2
C11—C10—H10	120.1	C21—C22—H22	120.2
C12—C11—C10	120.47 (17)	C24—C23—C22	120.24 (18)
C12—C11—H11	119.8	C24—C23—H23	119.9
C10—C11—H11	119.8	C22—C23—H23	119.9
C11—C12—C7	119.92 (17)	C23—C24—C25	120.37 (18)
C11—C12—H12	120.0	C23—C24—H24	119.8
C7—C12—H12	120.0	C25—C24—H24	119.8
C18—C13—C14	119.71 (15)	C20—C25—C24	119.52 (17)
C18—C13—C3	122.06 (15)	C20—C25—H25	120.2
C14—C13—C3	118.20 (16)	C24—C25—H25	120.2
C15—C14—C13	120.18 (17)
C19—N1—N2—C3	−123.18 (17)	N2—C3—C13—C14	−25.1 (2)
C6—N1—N2—C3	41.0 (2)	N4—C3—C13—C14	155.04 (17)
C3—N4—N5—C6	33.1 (2)	C18—C13—C14—C15	−0.1 (3)
N1—N2—C3—N4	−8.0 (2)	C3—C13—C14—C15	−178.39 (17)
N1—N2—C3—C13	172.13 (14)	C13—C14—C15—C16	0.5 (3)
N5—N4—C3—N2	−30.0 (2)	C14—C15—C16—C17	−0.3 (3)
N5—N4—C3—C13	149.85 (15)	C15—C16—C17—C18	−0.2 (3)
N4—N5—C6—N1	0.9 (2)	C14—C13—C18—C17	−0.4 (3)
N4—N5—C6—C7	−173.36 (15)	C3—C13—C18—C17	177.78 (17)
C19—N1—C6—N5	124.94 (18)	C16—C17—C18—C13	0.6 (3)
N2—N1—C6—N5	−38.8 (2)	C6—N1—C19—O1	5.0 (2)
C19—N1—C6—C7	−60.7 (2)	N2—N1—C19—O1	168.06 (15)
N2—N1—C6—C7	135.50 (16)	C6—N1—C19—C20	−176.05 (15)
N5—C6—C7—C8	154.45 (17)	N2—N1—C19—C20	−13.0 (2)
N1—C6—C7—C8	−19.8 (2)	O1—C19—C20—C25	130.67 (18)
N5—C6—C7—C12	−23.1 (3)	N1—C19—C20—C25	−48.2 (2)
N1—C6—C7—C12	162.63 (17)	O1—C19—C20—C21	−45.1 (2)
C12—C7—C8—C9	−0.1 (3)	N1—C19—C20—C21	136.01 (17)
C6—C7—C8—C9	−177.77 (17)	C25—C20—C21—C22	1.2 (3)
C7—C8—C9—C10	−0.1 (3)	C19—C20—C21—C22	177.08 (16)
C8—C9—C10—C11	0.1 (3)	C20—C21—C22—C23	−2.1 (3)
C9—C10—C11—C12	0.2 (3)	C21—C22—C23—C24	1.4 (3)
C10—C11—C12—C7	−0.5 (3)	C22—C23—C24—C25	0.1 (3)
C8—C7—C12—C11	0.4 (3)	C21—C20—C25—C24	0.3 (3)
C6—C7—C12—C11	178.06 (17)	C19—C20—C25—C24	−175.30 (15)
N2—C3—C13—C18	156.66 (17)	C23—C24—C25—C20	−1.0 (3)
N4—C3—C13—C18	−23.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4N···O1i	0.91 (2)	1.97 (2)	2.806 (2)	150.9 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4N⋯O1i	0.91 (2)	1.97 (2)	2.806 (2)	150.9 (18)

Symmetry code: (i) .