3-(4-Methoxy­phen­yl)-6-methyl-1,2,4,5-tetra­zine

In the title compound, C₁₀H₁₀N₄O, the tetra­zine ring is twisted with respect to the benzene ring, with a dihedral angle of 14.8 (4)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.059
• wR factor = 0.181
• Data-to-parameter ratio = 15.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         45 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C8      ..       6.76 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 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

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Computing details

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

3-(4-Methoxyphenyl)-6-methyl-1,2,4,5-tetrazine

Crystal data

C10H10N4O	F(000) = 424
Mr = 202.22	Dx = 1.337 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 933 reflections
a = 11.861 (5) Å	θ = 3.3–22.8°
b = 7.111 (3) Å	µ = 0.09 mm^−1
c = 11.996 (5) Å	T = 293 K
β = 96.987 (7)°	Prism, red
V = 1004.3 (7) Å^3	0.18 × 0.15 × 0.12 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	972 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
Graphite monochromator	θmax = 27.0°, θmin = 3.3°
φ and ω scans	h = −15→11
4732 measured reflections	k = −9→9
2161 independent reflections	l = −15→14

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)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.181	w = 1/[σ^2(Fo^2) + (0.0862P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
2161 reflections	Δρmax = 0.15 e Å^−3
139 parameters	Δρmin = −0.20 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: 0.019 (5)

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
O1	0.82982 (15)	0.9096 (3)	0.66637 (14)	0.0855 (6)
N1	0.26311 (19)	0.8858 (3)	0.91173 (16)	0.0770 (6)
N2	0.36828 (17)	0.8883 (3)	0.88454 (15)	0.0708 (6)
C3	0.3829 (2)	0.9010 (3)	0.77528 (17)	0.0562 (6)
N4	0.29599 (18)	0.9185 (3)	0.69234 (16)	0.0742 (7)
N5	0.19077 (19)	0.9127 (3)	0.71909 (18)	0.0812 (7)
C6	0.1782 (2)	0.8940 (3)	0.8284 (2)	0.0716 (7)
C7	0.0597 (2)	0.8845 (5)	0.8587 (2)	0.1050 (10)
H7A	0.0620	0.8698	0.9385	0.158*
H7B	0.0210	0.7792	0.8215	0.158*
H7C	0.0201	0.9983	0.8356	0.158*
C8	0.4982 (2)	0.9008 (3)	0.74451 (16)	0.0532 (6)
C9	0.5189 (2)	0.8730 (3)	0.63455 (17)	0.0614 (7)
H9	0.4579	0.8528	0.5794	0.074*
C10	0.6277 (2)	0.8744 (3)	0.60451 (19)	0.0653 (7)
H10	0.6397	0.8552	0.5302	0.078*
C11	0.7187 (2)	0.9049 (3)	0.68631 (19)	0.0639 (6)
C12	0.7000 (2)	0.9325 (3)	0.79739 (18)	0.0656 (7)
H12	0.7613	0.9521	0.8523	0.079*
C13	0.5916 (2)	0.9308 (3)	0.82638 (18)	0.0611 (7)
H13	0.5799	0.9496	0.9008	0.073*
C14	0.8533 (2)	0.8930 (4)	0.5531 (2)	0.0966 (10)
H14A	0.8236	0.7759	0.5224	0.145*
H14B	0.9339	0.8967	0.5510	0.145*
H14C	0.8181	0.9952	0.5096	0.145*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0738 (12)	0.1213 (16)	0.0618 (11)	0.0058 (10)	0.0103 (9)	0.0088 (9)
N1	0.0790 (15)	0.0960 (17)	0.0551 (13)	−0.0075 (12)	0.0051 (12)	0.0014 (10)
N2	0.0743 (15)	0.0859 (16)	0.0506 (12)	−0.0085 (11)	0.0014 (11)	0.0024 (9)
C3	0.0767 (16)	0.0475 (14)	0.0413 (13)	0.0002 (11)	−0.0050 (12)	−0.0010 (9)
N4	0.0745 (15)	0.0935 (17)	0.0529 (13)	0.0105 (12)	0.0003 (11)	0.0015 (10)
N5	0.0754 (15)	0.1076 (18)	0.0583 (13)	0.0085 (12)	−0.0010 (11)	−0.0024 (11)
C6	0.0729 (17)	0.0791 (18)	0.0621 (16)	0.0015 (13)	0.0057 (14)	−0.0008 (13)
C7	0.082 (2)	0.146 (3)	0.089 (2)	0.0000 (18)	0.0138 (18)	0.0011 (18)
C8	0.0666 (14)	0.0483 (13)	0.0432 (13)	0.0005 (11)	0.0008 (11)	0.0035 (10)
C9	0.0767 (17)	0.0614 (16)	0.0425 (12)	−0.0009 (11)	−0.0075 (12)	−0.0011 (10)
C10	0.0837 (18)	0.0684 (17)	0.0437 (13)	0.0026 (13)	0.0077 (13)	−0.0005 (10)
C11	0.0720 (17)	0.0661 (16)	0.0527 (14)	0.0040 (12)	0.0033 (13)	0.0088 (11)
C12	0.0693 (16)	0.0771 (18)	0.0473 (13)	0.0020 (13)	−0.0055 (12)	0.0034 (11)
C13	0.0796 (17)	0.0620 (16)	0.0400 (12)	0.0043 (12)	0.0010 (12)	0.0040 (10)
C14	0.094 (2)	0.125 (3)	0.0756 (18)	0.0026 (17)	0.0291 (16)	0.0003 (16)

Geometric parameters (Å, º)

O1—C11	1.368 (3)	C8—C9	1.385 (3)
O1—C14	1.424 (3)	C8—C13	1.404 (3)
N1—N2	1.327 (3)	C9—C10	1.382 (3)
N1—C6	1.331 (3)	C9—H9	0.9300
N2—C3	1.346 (3)	C10—C11	1.385 (3)
C3—N4	1.348 (3)	C10—H10	0.9300
C3—C8	1.460 (3)	C11—C12	1.391 (3)
N4—N5	1.327 (3)	C12—C13	1.372 (3)
N5—C6	1.344 (3)	C12—H12	0.9300
C6—C7	1.495 (3)	C13—H13	0.9300
C7—H7A	0.9599	C14—H14A	0.9599
C7—H7B	0.9599	C14—H14B	0.9599
C7—H7C	0.9599	C14—H14C	0.9599
C11—O1—C14	118.0 (2)	C10—C9—H9	119.1
N2—N1—C6	117.6 (2)	C8—C9—H9	119.1
N1—N2—C3	118.5 (2)	C9—C10—C11	119.3 (2)
N2—C3—N4	123.2 (2)	C9—C10—H10	120.4
N2—C3—C8	118.8 (2)	C11—C10—H10	120.4
N4—C3—C8	117.99 (19)	O1—C11—C10	124.4 (2)
N5—N4—C3	118.4 (2)	O1—C11—C12	115.7 (2)
N4—N5—C6	117.3 (2)	C10—C11—C12	120.0 (2)
N1—C6—N5	125.0 (2)	C13—C12—C11	120.3 (2)
N1—C6—C7	117.6 (2)	C13—C12—H12	119.8
N5—C6—C7	117.4 (3)	C11—C12—H12	119.8
C6—C7—H7A	109.5	C12—C13—C8	120.5 (2)
C6—C7—H7B	109.5	C12—C13—H13	119.7
H7A—C7—H7B	109.5	C8—C13—H13	119.7
C6—C7—H7C	109.5	O1—C14—H14A	109.5
H7A—C7—H7C	109.5	O1—C14—H14B	109.5
H7B—C7—H7C	109.5	H14A—C14—H14B	109.5
C9—C8—C13	118.2 (2)	O1—C14—H14C	109.5
C9—C8—C3	121.4 (2)	H14A—C14—H14C	109.5
C13—C8—C3	120.44 (19)	H14B—C14—H14C	109.5
C10—C9—C8	121.8 (2)
C6—N1—N2—C3	0.7 (3)	N4—C3—C8—C13	163.89 (19)
N1—N2—C3—N4	2.6 (3)	C13—C8—C9—C10	−0.1 (3)
N1—N2—C3—C8	−179.00 (18)	C3—C8—C9—C10	179.32 (19)
N2—C3—N4—N5	−3.7 (3)	C8—C9—C10—C11	−0.1 (3)
C8—C3—N4—N5	177.85 (19)	C14—O1—C11—C10	3.8 (3)
C3—N4—N5—C6	1.5 (3)	C14—O1—C11—C12	−176.4 (2)
N2—N1—C6—N5	−2.9 (4)	C9—C10—C11—O1	−179.9 (2)
N2—N1—C6—C7	177.9 (2)	C9—C10—C11—C12	0.4 (3)
N4—N5—C6—N1	1.8 (4)	O1—C11—C12—C13	179.87 (19)
N4—N5—C6—C7	−179.1 (2)	C10—C11—C12—C13	−0.4 (3)
N2—C3—C8—C9	165.98 (18)	C11—C12—C13—C8	0.1 (3)
N4—C3—C8—C9	−15.5 (3)	C9—C8—C13—C12	0.1 (3)
N2—C3—C8—C13	−14.6 (3)	C3—C8—C13—C12	−179.3 (2)