Crystal structure of 3,6-bis­(pyridin-2-yl)-1,4-di­hydro-1,2,4,5-tetra­zine

In the crystal structure, inter­molecular N—H...N hydrogen bonds link the mol­ecules into infinite ribbons extending along the [100] direction.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.035
• wR factor = 0.095
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   2 ALERT level G = General information/check it is not something unexpected

   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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: WinGX (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

3,6-Bis(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazine

Crystal data

C12H10N6	F(000) = 496
Mr = 238.26	Dx = 1.461 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 5.4603 (1) Å	Cell parameters from 3734 reflections
b = 12.7845 (3) Å	θ = 4.5–76.4°
c = 15.6474 (4) Å	µ = 0.78 mm^−1
β = 97.281 (2)°	T = 100 K
V = 1083.49 (4) Å^3	Plate, yellow
Z = 4	0.11 × 0.10 × 0.08 mm

Data collection

Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	2004 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1767 reflections with I > 2σ(I)
Detector resolution: 10.4052 pixels mm^-1	Rint = 0.027
ω scans	θmax = 68.5°, θmin = 4.5°
Absorption correction: multi-scan (CrysAlisPRO; Rigaku OD, 2015)	h = −6→6
Tmin = 0.958, Tmax = 1.000	k = −15→14
8686 measured reflections	l = −18→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 0.2596P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
2004 reflections	Δρmax = 0.14 e Å^−3
171 parameters	Δρmin = −0.24 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N5	0.3304 (2)	0.59460 (9)	0.30162 (7)	0.0159 (3)
N1	0.7587 (2)	0.61063 (9)	0.30346 (7)	0.0167 (3)
N66	0.7195 (2)	0.45247 (9)	0.18218 (7)	0.0178 (3)
N4	0.3800 (2)	0.66133 (9)	0.37517 (7)	0.0162 (3)
N2	0.7969 (2)	0.61146 (9)	0.39548 (7)	0.0166 (3)
N36	0.4117 (2)	0.70258 (9)	0.54575 (7)	0.0196 (3)
C3	0.6017 (2)	0.63816 (10)	0.42759 (9)	0.0151 (3)
C31	0.6094 (2)	0.65389 (10)	0.52161 (8)	0.0159 (3)
C6	0.5274 (2)	0.57389 (10)	0.26787 (8)	0.0150 (3)
C61	0.5133 (2)	0.50651 (10)	0.19059 (8)	0.0153 (3)
C62	0.2981 (2)	0.49884 (11)	0.13279 (8)	0.0183 (3)
H62	0.1608	0.5397	0.1394	0.022*
C65	0.7096 (2)	0.38393 (10)	0.11717 (9)	0.0191 (3)
H65	0.8497	0.3444	0.1116	0.023*
C64	0.5020 (3)	0.36871 (11)	0.05778 (9)	0.0194 (3)
H64	0.5020	0.3195	0.0140	0.023*
C34	0.6135 (3)	0.69920 (11)	0.69170 (9)	0.0201 (3)
H34	0.6106	0.7167	0.7493	0.024*
C32	0.8134 (3)	0.62397 (11)	0.57895 (9)	0.0196 (3)
H32	0.9460	0.5895	0.5596	0.024*
C63	0.2943 (3)	0.42869 (11)	0.06517 (9)	0.0201 (3)
H63	0.1539	0.4219	0.0252	0.024*
C33	0.8137 (3)	0.64675 (11)	0.66537 (9)	0.0215 (3)
H33	0.9465	0.6272	0.7054	0.026*
C35	0.4179 (3)	0.72475 (11)	0.62978 (9)	0.0211 (3)
H35	0.2832	0.7593	0.6476	0.025*
H1	0.886 (3)	0.5796 (14)	0.2850 (11)	0.022 (4)*
H4	0.253 (4)	0.6611 (15)	0.4051 (13)	0.030 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N5	0.0158 (5)	0.0169 (5)	0.0144 (5)	0.0008 (4)	−0.0001 (4)	−0.0012 (4)
N1	0.0134 (5)	0.0221 (6)	0.0148 (5)	−0.0014 (5)	0.0020 (4)	−0.0020 (4)
N66	0.0154 (5)	0.0182 (6)	0.0198 (6)	0.0000 (4)	0.0025 (4)	−0.0009 (4)
N4	0.0138 (5)	0.0196 (6)	0.0150 (6)	0.0025 (4)	0.0007 (4)	−0.0025 (4)
N2	0.0159 (5)	0.0191 (6)	0.0145 (5)	−0.0009 (4)	0.0003 (4)	−0.0013 (4)
N36	0.0174 (6)	0.0229 (6)	0.0181 (6)	0.0010 (4)	0.0009 (4)	−0.0024 (4)
C3	0.0138 (6)	0.0136 (6)	0.0173 (7)	−0.0002 (5)	−0.0001 (5)	0.0003 (5)
C31	0.0161 (6)	0.0144 (6)	0.0170 (7)	−0.0025 (5)	0.0015 (5)	0.0009 (5)
C6	0.0137 (6)	0.0149 (6)	0.0162 (6)	0.0006 (5)	0.0007 (5)	0.0022 (5)
C61	0.0151 (6)	0.0144 (6)	0.0166 (6)	−0.0010 (5)	0.0032 (5)	0.0015 (5)
C62	0.0153 (6)	0.0211 (7)	0.0185 (7)	0.0017 (5)	0.0018 (5)	0.0005 (5)
C65	0.0168 (6)	0.0175 (6)	0.0236 (7)	0.0007 (5)	0.0055 (5)	−0.0018 (5)
C64	0.0223 (7)	0.0183 (6)	0.0181 (7)	−0.0027 (5)	0.0049 (5)	−0.0025 (5)
C34	0.0253 (7)	0.0193 (7)	0.0155 (6)	−0.0053 (5)	0.0017 (5)	−0.0006 (5)
C32	0.0180 (7)	0.0204 (7)	0.0203 (7)	0.0013 (5)	0.0019 (5)	0.0023 (5)
C63	0.0175 (6)	0.0237 (7)	0.0183 (7)	−0.0024 (5)	−0.0005 (5)	0.0002 (5)
C33	0.0212 (7)	0.0231 (7)	0.0190 (7)	−0.0019 (5)	−0.0024 (5)	0.0038 (5)
C35	0.0209 (7)	0.0226 (7)	0.0202 (7)	0.0000 (5)	0.0040 (5)	−0.0033 (5)

Geometric parameters (Å, º)

N5—C6	1.2848 (17)	C61—C62	1.3926 (18)
N5—N4	1.4306 (16)	C62—C63	1.385 (2)
N1—C6	1.3953 (17)	C62—H62	0.9300
N1—N2	1.4285 (15)	C65—C64	1.386 (2)
N1—H1	0.880 (19)	C65—H65	0.9300
N66—C65	1.3384 (18)	C64—C63	1.386 (2)
N66—C61	1.3416 (17)	C64—H64	0.9300
N4—C3	1.4051 (17)	C34—C35	1.387 (2)
N4—H4	0.88 (2)	C34—C33	1.389 (2)
N2—C3	1.2809 (18)	C34—H34	0.9300
N36—C35	1.3412 (18)	C32—C33	1.383 (2)
N36—C31	1.3415 (18)	C32—H32	0.9300
C3—C31	1.4800 (18)	C63—H63	0.9300
C31—C32	1.3922 (19)	C33—H33	0.9300
C6—C61	1.4786 (18)	C35—H35	0.9300
C6—N5—N4	111.75 (11)	C63—C62—H62	120.9
C6—N1—N2	114.45 (10)	C61—C62—H62	120.9
C6—N1—H1	115.4 (12)	N66—C65—C64	123.53 (12)
N2—N1—H1	108.3 (12)	N66—C65—H65	118.2
C65—N66—C61	117.28 (12)	C64—C65—H65	118.2
C3—N4—N5	113.90 (10)	C65—C64—C63	118.36 (13)
C3—N4—H4	111.4 (13)	C65—C64—H64	120.8
N5—N4—H4	110.1 (13)	C63—C64—H64	120.8
C3—N2—N1	112.02 (11)	C35—C34—C33	118.16 (13)
C35—N36—C31	116.93 (12)	C35—C34—H34	120.9
N2—C3—N4	121.69 (12)	C33—C34—H34	120.9
N2—C3—C31	120.37 (12)	C33—C32—C31	118.30 (13)
N4—C3—C31	117.75 (12)	C33—C32—H32	120.9
N36—C31—C32	123.55 (12)	C31—C32—H32	120.9
N36—C31—C3	114.85 (12)	C62—C63—C64	119.26 (13)
C32—C31—C3	121.54 (12)	C62—C63—H63	120.4
N5—C6—N1	121.95 (12)	C64—C63—H63	120.4
N5—C6—C61	119.77 (12)	C32—C33—C34	119.21 (13)
N1—C6—C61	118.25 (11)	C32—C33—H33	120.4
N66—C61—C62	123.33 (12)	C34—C33—H33	120.4
N66—C61—C6	115.02 (11)	N36—C35—C34	123.82 (13)
C62—C61—C6	121.63 (12)	N36—C35—H35	118.1
C63—C62—C61	118.13 (12)	C34—C35—H35	118.1
N2—C3—N4—H4	164.1 (13)	C3—N2—N1—H1	−168.4 (12)
C6—N5—N4—H4	−165.2 (14)	N5—C6—N1—H1	164.3 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2^i	0.89 (2)	2.56 (2)	3.3017 (16)	142.5 (17)
N1—H1···N5^ii	0.880 (17)	2.415 (17)	3.1321 (16)	138.9 (15)

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