X-ray studies of three 3,6-bis­(pyri­din-2-yl)-1,2,4,5-tetra­zine cocrystals: an unexpected mol­ecular conformation stabilized by hydrogen bonds

The results of the X-ray structure analysis of three novel 3,6-bis­(pyri­din-2-yl)-1,2,4,5-tetra­zine cocrystals are presented. These are 3,6-bis­(pyri­din-2-yl)-1,2,4,5-tetra­zine–2,4,6-tri­bromo­phenol (1/2), C₁₂H₈N₆·2C₆H₃Br₃O, 3,6-bis­(pyri­din-2-yl)-1,2,4,5-tetra­zine–isonicotinic acid N-oxide (1/2), C₁₂H₈N₆·2C₆H₅NO₃, and 3,6-bis­(pyri­din-2-yl)-1,2,4,5-tetra­zine–4-nitro­benzene­sulfonamide (1/1), C₁₂H₈N₆·C₆H₆N₂O₄S. Special attention is paid to a conformational analysis of the title tetra­zine mol­ecule in known crystal structures. Quantum chemistry methods are used to com­pare the energetic parameters of the investigated conformations. A structural analysis of the hydrogen and halogen bonds with acceptor aromatic tetra­zine and pyrazine rings is conducted in order to elucidate factors responsible for conformational stability.

Computing details

3,6-Bis(pyridin-2-yl)-1,2,4,5-tetrazine–2,4,6-tribromophenol (1/2) (I)

Crystal data

C12H8N6·2C6H3Br3O	Z = 1
Mr = 897.81	F(000) = 426
Triclinic, P1	Dx = 2.252 Mg m^−3
a = 4.6374 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 11.0096 (6) Å	Cell parameters from 4275 reflections
c = 13.0262 (7) Å	θ = 3.4–76.4°
α = 93.420 (4)°	µ = 11.27 mm^−1
β = 94.065 (4)°	T = 293 K
γ = 90.317 (4)°	Plate, pink
V = 662.18 (6) Å^3	0.32 × 0.08 × 0.04 mm

Data collection

Rigaku OD SuperNova (Dual, Cu at home/near) diffractometer with an Atlas detector	2453 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	2256 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.035
Detector resolution: 10.4052 pixels mm^-1	θmax = 68.5°, θmin = 3.4°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −13→8
Tmin = 0.399, Tmax = 1.000	l = −15→15
7368 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.030	w = 1/[σ^2(Fo^2) + (0.0549P)^2 + 0.1998P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.080	(Δ/σ)max < 0.001
S = 1.05	Δρmax = 0.49 e Å^−3
2453 reflections	Δρmin = −0.85 e Å^−3
177 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00063 (18)
Primary atom site location: iterative

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
Br16	0.72905 (8)	0.51264 (3)	0.19725 (3)	0.02072 (13)
Br12	−0.02038 (7)	0.10806 (3)	0.22548 (2)	0.01897 (13)
Br14	0.56558 (9)	0.15737 (3)	−0.13458 (3)	0.02480 (14)
C15	0.6032 (7)	0.3280 (3)	0.0393 (3)	0.0206 (7)
H15	0.725097	0.372361	0.001590	0.025*
C16	0.5461 (7)	0.3670 (3)	0.1383 (2)	0.0175 (6)
C11	0.3698 (7)	0.3027 (3)	0.1984 (2)	0.0181 (7)
C13	0.2872 (7)	0.1550 (3)	0.0516 (3)	0.0192 (7)
H13	0.198005	0.084209	0.022140	0.023*
C14	0.4738 (8)	0.2206 (3)	−0.0024 (2)	0.0187 (7)
C12	0.2362 (7)	0.1976 (3)	0.1510 (2)	0.0167 (6)
O11	0.3383 (5)	0.3448 (2)	0.29642 (18)	0.0190 (5)
N32	0.0733 (6)	0.2651 (2)	0.4602 (2)	0.0160 (5)
N2	0.4761 (6)	0.0901 (3)	0.4317 (2)	0.0196 (6)
C33	−0.1167 (7)	0.3550 (3)	0.4751 (3)	0.0185 (7)
H33	−0.161399	0.405086	0.421348	0.022*
C3	0.3285 (7)	0.0892 (3)	0.5170 (2)	0.0162 (6)
C31	0.1266 (7)	0.1901 (3)	0.5370 (2)	0.0157 (6)
N1	0.3483 (6)	0.0023 (3)	0.5857 (2)	0.0194 (6)
C35	−0.1900 (8)	0.3006 (3)	0.6454 (3)	0.0195 (7)
H35	−0.275160	0.313340	0.707557	0.023*
C36	−0.0011 (7)	0.2045 (3)	0.6306 (2)	0.0180 (6)
H36	0.039323	0.150894	0.682107	0.022*
C34	−0.2493 (7)	0.3770 (3)	0.5658 (3)	0.0190 (7)
H34	−0.375599	0.441667	0.573475	0.023*
H11	0.263 (9)	0.295 (4)	0.324 (3)	0.022 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br16	0.0285 (2)	0.0145 (2)	0.0190 (2)	−0.00484 (14)	0.00083 (14)	0.00078 (13)
Br12	0.0209 (2)	0.0168 (2)	0.0195 (2)	−0.00331 (13)	0.00226 (14)	0.00268 (13)
Br14	0.0418 (3)	0.0192 (2)	0.0138 (2)	−0.00179 (15)	0.00553 (15)	0.00047 (13)
C15	0.0241 (17)	0.0198 (17)	0.0185 (16)	0.0005 (13)	0.0014 (13)	0.0066 (13)
C16	0.0233 (17)	0.0140 (15)	0.0146 (15)	−0.0010 (12)	−0.0031 (12)	0.0024 (11)
C11	0.0230 (17)	0.0160 (16)	0.0154 (15)	0.0052 (13)	−0.0006 (12)	0.0029 (12)
C13	0.0225 (17)	0.0167 (16)	0.0180 (16)	−0.0006 (13)	−0.0022 (13)	0.0017 (12)
C14	0.0267 (18)	0.0182 (16)	0.0113 (14)	0.0008 (13)	0.0010 (12)	0.0021 (12)
C12	0.0214 (16)	0.0141 (15)	0.0148 (15)	−0.0018 (12)	0.0002 (12)	0.0052 (11)
O11	0.0293 (13)	0.0160 (12)	0.0118 (11)	−0.0043 (10)	0.0030 (9)	0.0008 (9)
N32	0.0193 (14)	0.0155 (13)	0.0132 (13)	−0.0020 (10)	0.0015 (10)	0.0022 (10)
N2	0.0204 (14)	0.0179 (14)	0.0208 (14)	0.0004 (11)	0.0007 (11)	0.0034 (10)
C33	0.0237 (17)	0.0117 (15)	0.0197 (16)	−0.0020 (12)	−0.0036 (13)	0.0031 (12)
C3	0.0156 (15)	0.0155 (16)	0.0170 (15)	−0.0023 (12)	−0.0022 (12)	0.0013 (12)
C31	0.0174 (15)	0.0146 (15)	0.0144 (15)	−0.0030 (12)	−0.0036 (12)	0.0014 (11)
N1	0.0206 (14)	0.0191 (14)	0.0188 (14)	0.0004 (11)	0.0006 (11)	0.0045 (11)
C35	0.0233 (17)	0.0196 (16)	0.0151 (15)	−0.0022 (13)	0.0005 (12)	−0.0025 (12)
C36	0.0223 (17)	0.0161 (16)	0.0160 (15)	−0.0038 (12)	0.0009 (12)	0.0055 (12)
C34	0.0248 (17)	0.0144 (16)	0.0177 (15)	0.0011 (13)	0.0004 (13)	0.0011 (12)

Geometric parameters (Å, º)

Br16—C16	1.904 (3)	N32—C31	1.345 (4)
Br12—C12	1.896 (3)	N2—C3	1.347 (4)
Br14—C14	1.896 (3)	N2—N1^i	1.326 (4)
C15—H15	0.9300	C33—H33	0.9300
C15—C16	1.379 (5)	C33—C34	1.380 (5)
C15—C14	1.387 (5)	C3—C31	1.480 (5)
C16—C11	1.390 (5)	C3—N1	1.348 (4)
C11—C12	1.398 (4)	C31—C36	1.393 (5)
C11—O11	1.350 (4)	C35—H35	0.9300
C13—H13	0.9300	C35—C36	1.390 (5)
C13—C14	1.379 (5)	C35—C34	1.387 (5)
C13—C12	1.387 (5)	C36—H36	0.9300
O11—H11	0.76 (5)	C34—H34	0.9300
N32—C33	1.343 (4)
C16—C15—H15	120.9	N1^i—N2—C3	117.0 (3)
C16—C15—C14	118.1 (3)	N32—C33—H33	118.2
C14—C15—H15	120.9	N32—C33—C34	123.6 (3)
C15—C16—Br16	118.4 (3)	C34—C33—H33	118.2
C15—C16—C11	123.0 (3)	N2—C3—C31	118.0 (3)
C11—C16—Br16	118.5 (2)	N2—C3—N1	124.9 (3)
C16—C11—C12	116.3 (3)	N1—C3—C31	117.1 (3)
O11—C11—C16	118.9 (3)	N32—C31—C3	116.4 (3)
O11—C11—C12	124.8 (3)	N32—C31—C36	122.7 (3)
C14—C13—H13	120.9	C36—C31—C3	121.0 (3)
C14—C13—C12	118.2 (3)	N2^i—N1—C3	118.1 (3)
C12—C13—H13	120.9	C36—C35—H35	120.5
C15—C14—Br14	119.7 (3)	C34—C35—H35	120.5
C13—C14—Br14	118.6 (2)	C34—C35—C36	118.9 (3)
C13—C14—C15	121.7 (3)	C31—C36—H36	120.7
C11—C12—Br12	119.1 (2)	C35—C36—C31	118.7 (3)
C13—C12—Br12	118.4 (2)	C35—C36—H36	120.7
C13—C12—C11	122.5 (3)	C33—C34—C35	118.5 (3)
C11—O11—H11	108 (3)	C33—C34—H34	120.7
C33—N32—C31	117.5 (3)	C35—C34—H34	120.7
Br16—C16—C11—C12	178.9 (2)	N32—C33—C34—C35	−1.8 (5)
Br16—C16—C11—O11	−1.0 (4)	N32—C31—C36—C35	−0.3 (5)
C15—C16—C11—C12	−3.6 (5)	N2—C3—C31—N32	9.9 (4)
C15—C16—C11—O11	176.6 (3)	N2—C3—C31—C36	−170.7 (3)
C16—C15—C14—Br14	−175.8 (2)	N2—C3—N1—N2^i	−0.6 (5)
C16—C15—C14—C13	1.5 (5)	C33—N32—C31—C3	177.8 (3)
C16—C11—C12—Br12	−177.4 (2)	C33—N32—C31—C36	−1.6 (5)
C16—C11—C12—C13	3.5 (5)	C3—C31—C36—C35	−179.8 (3)
C14—C15—C16—Br16	178.7 (2)	C31—N32—C33—C34	2.7 (5)
C14—C15—C16—C11	1.2 (5)	C31—C3—N1—N2^i	178.8 (3)
C14—C13—C12—Br12	179.9 (2)	N1^i—N2—C3—C31	−178.8 (3)
C14—C13—C12—C11	−1.0 (5)	N1^i—N2—C3—N1	0.6 (5)
C12—C13—C14—Br14	175.7 (2)	N1—C3—C31—N32	−169.6 (3)
C12—C13—C14—C15	−1.6 (5)	N1—C3—C31—C36	9.9 (4)
O11—C11—C12—Br12	2.4 (5)	C36—C35—C34—C33	−0.4 (5)
O11—C11—C12—C13	−176.7 (3)	C34—C35—C36—C31	1.3 (5)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O11—H11···N32	0.76 (5)	2.08 (5)	2.723 (4)	142 (4)

3,6-Bis(pyridin-2-yl)-1,2,4,5-tetrazine–4-carboxypyridine N-oxide (1/2) (II)

Crystal data

C12H8N6·2C6H5NO3	F(000) = 532
Mr = 514.46	Dx = 1.545 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 3.8067 (2) Å	Cell parameters from 4366 reflections
b = 21.3885 (7) Å	θ = 3.9–76.2°
c = 14.2669 (6) Å	µ = 0.97 mm^−1
β = 107.835 (5)°	T = 293 K
V = 1105.78 (9) Å^3	Plate, pink
Z = 2	0.26 × 0.08 × 0.04 mm

Data collection

Rigaku OD SuperNova (Dual, Cu at home/near) diffractometer with an Atlas detector	2048 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	1806 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.047
Detector resolution: 10.4052 pixels mm^-1	θmax = 68.5°, θmin = 3.9°
ω scans	h = −4→4
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −25→21
Tmin = 0.886, Tmax = 1.000	l = −17→17
10838 measured reflections

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0682P)^2 + 0.2944P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
2048 reflections	Δρmax = 0.24 e Å^−3
176 parameters	Δρmin = −0.30 e Å^−3
0 restraints

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
O11	0.0482 (3)	0.36504 (5)	0.88197 (8)	0.0185 (3)
O141	−0.1328 (3)	0.28463 (5)	0.44542 (8)	0.0179 (3)
O142	0.1565 (3)	0.20133 (5)	0.53135 (8)	0.0199 (3)
N11	0.0458 (3)	0.33948 (6)	0.79700 (9)	0.0132 (3)
N1	1.1510 (3)	0.44888 (6)	0.47045 (10)	0.0159 (3)
N2	0.7372 (4)	0.53549 (6)	0.43554 (10)	0.0159 (3)
N32	0.5662 (3)	0.51014 (6)	0.24112 (10)	0.0162 (3)
C13	−0.1522 (4)	0.34222 (7)	0.62322 (11)	0.0131 (3)
H13	−0.279926	0.362247	0.564875	0.016*
C12	−0.1422 (4)	0.36841 (7)	0.71227 (11)	0.0136 (3)
H12	−0.264466	0.405830	0.714041	0.016*
C141	0.0080 (4)	0.25757 (7)	0.52272 (11)	0.0135 (3)
C15	0.2192 (4)	0.25747 (7)	0.70881 (11)	0.0137 (3)
H15	0.341600	0.219858	0.708654	0.016*
C16	0.2274 (4)	0.28480 (7)	0.79662 (11)	0.0139 (3)
H16	0.357243	0.265892	0.855793	0.017*
C14	0.0281 (4)	0.28593 (7)	0.62008 (11)	0.0123 (3)
C3	0.8910 (4)	0.48456 (7)	0.40830 (11)	0.0135 (3)
C35	0.7397 (4)	0.39601 (7)	0.17179 (12)	0.0179 (3)
H35	0.797713	0.358080	0.148287	0.021*
C34	0.5300 (4)	0.44019 (8)	0.10720 (12)	0.0184 (3)
H34	0.444011	0.432303	0.039907	0.022*
C33	0.4516 (4)	0.49631 (7)	0.14517 (11)	0.0171 (3)
H33	0.311986	0.525837	0.101626	0.021*
C36	0.8615 (4)	0.40915 (7)	0.27179 (12)	0.0166 (3)
H36	1.000670	0.380298	0.316770	0.020*
C31	0.7687 (4)	0.46704 (7)	0.30281 (11)	0.0137 (3)
H142	0.098 (7)	0.1794 (12)	0.4615 (19)	0.042 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O11	0.0288 (6)	0.0144 (5)	0.0120 (5)	0.0014 (4)	0.0058 (4)	−0.0018 (4)
O141	0.0216 (6)	0.0164 (5)	0.0129 (5)	0.0000 (4)	0.0012 (4)	0.0014 (4)
O142	0.0293 (6)	0.0142 (5)	0.0142 (5)	0.0050 (4)	0.0039 (5)	−0.0004 (4)
N11	0.0151 (6)	0.0124 (6)	0.0114 (6)	−0.0022 (5)	0.0030 (5)	−0.0012 (5)
N1	0.0171 (6)	0.0137 (6)	0.0158 (6)	−0.0004 (5)	0.0034 (5)	0.0002 (5)
N2	0.0177 (6)	0.0126 (6)	0.0165 (6)	0.0013 (5)	0.0037 (5)	0.0000 (5)
N32	0.0164 (6)	0.0139 (6)	0.0174 (6)	0.0003 (5)	0.0035 (5)	0.0012 (5)
C13	0.0120 (6)	0.0125 (7)	0.0130 (7)	−0.0016 (5)	0.0011 (5)	0.0025 (5)
C12	0.0137 (7)	0.0104 (7)	0.0153 (7)	−0.0011 (5)	0.0025 (5)	0.0020 (5)
C141	0.0121 (6)	0.0126 (7)	0.0152 (7)	−0.0033 (5)	0.0032 (5)	0.0002 (5)
C15	0.0123 (6)	0.0114 (7)	0.0168 (7)	−0.0008 (5)	0.0036 (5)	0.0005 (5)
C16	0.0130 (7)	0.0117 (7)	0.0151 (7)	0.0004 (5)	0.0012 (5)	0.0019 (5)
C14	0.0106 (7)	0.0114 (7)	0.0143 (8)	−0.0036 (5)	0.0032 (5)	−0.0002 (5)
C3	0.0129 (7)	0.0098 (7)	0.0180 (8)	−0.0011 (5)	0.0050 (6)	0.0021 (5)
C35	0.0177 (7)	0.0139 (7)	0.0225 (8)	−0.0009 (6)	0.0067 (6)	−0.0040 (6)
C34	0.0181 (7)	0.0199 (8)	0.0172 (7)	−0.0025 (6)	0.0054 (6)	−0.0018 (6)
C33	0.0181 (7)	0.0149 (7)	0.0164 (7)	−0.0001 (6)	0.0024 (6)	0.0014 (6)
C36	0.0151 (7)	0.0132 (7)	0.0206 (8)	0.0002 (6)	0.0042 (6)	−0.0005 (6)
C31	0.0123 (7)	0.0127 (7)	0.0162 (7)	−0.0014 (5)	0.0046 (6)	0.0002 (6)

Geometric parameters (Å, º)

O11—N11	1.3273 (16)	C141—C14	1.496 (2)
O141—C141	1.2150 (19)	C15—H15	0.9300
O142—C141	1.3187 (19)	C15—C16	1.374 (2)
O142—H142	1.06 (3)	C15—C14	1.392 (2)
N11—C12	1.3515 (19)	C16—H16	0.9300
N11—C16	1.359 (2)	C3—C31	1.481 (2)
N1—N2^i	1.3200 (18)	C35—H35	0.9300
N1—C3	1.3454 (19)	C35—C34	1.389 (2)
N2—C3	1.349 (2)	C35—C36	1.387 (2)
N32—C33	1.336 (2)	C34—H34	0.9300
N32—C31	1.343 (2)	C34—C33	1.386 (2)
C13—H13	0.9300	C33—H33	0.9300
C13—C12	1.378 (2)	C36—H36	0.9300
C13—C14	1.393 (2)	C36—C31	1.396 (2)
C12—H12	0.9300
C141—O142—H142	110.8 (13)	C13—C14—C141	119.64 (13)
O11—N11—C12	118.81 (13)	C15—C14—C13	118.30 (13)
O11—N11—C16	119.79 (12)	C15—C14—C141	122.06 (13)
C12—N11—C16	121.40 (13)	N1—C3—N2	124.38 (14)
N2^i—N1—C3	117.99 (13)	N1—C3—C31	117.72 (14)
N1^i—N2—C3	117.63 (13)	N2—C3—C31	117.90 (13)
C33—N32—C31	117.46 (13)	C34—C35—H35	120.4
C12—C13—H13	119.8	C36—C35—H35	120.4
C12—C13—C14	120.40 (13)	C36—C35—C34	119.20 (14)
C14—C13—H13	119.8	C35—C34—H34	120.7
N11—C12—C13	119.73 (14)	C33—C34—C35	118.59 (15)
N11—C12—H12	120.1	C33—C34—H34	120.7
C13—C12—H12	120.1	N32—C33—C34	123.37 (14)
O141—C141—O142	125.21 (14)	N32—C33—H33	118.3
O141—C141—C14	122.18 (14)	C34—C33—H33	118.3
O142—C141—C14	112.61 (13)	C35—C36—H36	121.0
C16—C15—H15	119.9	C35—C36—C31	117.92 (14)
C16—C15—C14	120.17 (14)	C31—C36—H36	121.0
C14—C15—H15	119.9	N32—C31—C3	115.54 (13)
N11—C16—C15	120.00 (13)	N32—C31—C36	123.46 (14)
N11—C16—H16	120.0	C36—C31—C3	121.00 (13)
C15—C16—H16	120.0
O11—N11—C12—C13	−179.15 (12)	C12—C13—C14—C141	178.80 (13)
O11—N11—C16—C15	178.60 (13)	C12—C13—C14—C15	−0.5 (2)
O141—C141—C14—C13	6.8 (2)	C16—N11—C12—C13	0.1 (2)
O141—C141—C14—C15	−173.91 (13)	C16—C15—C14—C13	0.0 (2)
O142—C141—C14—C13	−172.98 (13)	C16—C15—C14—C141	−179.32 (13)
O142—C141—C14—C15	6.3 (2)	C14—C13—C12—N11	0.5 (2)
N1^i—N2—C3—N1	−0.2 (2)	C14—C15—C16—N11	0.6 (2)
N1^i—N2—C3—C31	−179.57 (12)	C35—C34—C33—N32	−0.3 (2)
N1—C3—C31—N32	−167.38 (13)	C35—C36—C31—N32	0.5 (2)
N1—C3—C31—C36	12.7 (2)	C35—C36—C31—C3	−179.58 (13)
N2^i—N1—C3—N2	0.2 (2)	C34—C35—C36—C31	−0.5 (2)
N2^i—N1—C3—C31	179.58 (12)	C33—N32—C31—C3	179.71 (12)
N2—C3—C31—N32	12.00 (19)	C33—N32—C31—C36	−0.4 (2)
N2—C3—C31—C36	−167.89 (14)	C36—C35—C34—C33	0.4 (2)
C12—N11—C16—C15	−0.6 (2)	C31—N32—C33—C34	0.3 (2)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N2^ii	0.93	2.65	3.2978 (19)	127
C12—H12···N32^ii	0.93	2.33	3.2329 (19)	165
O142—H142···O11^iii	1.06 (3)	1.45 (3)	2.4878 (15)	165 (2)
O142—H142···N11^iii	1.06 (3)	2.33 (3)	3.3549 (17)	162 (2)

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

3,6-Bis(pyridin-2-yl)-1,2,4,5-tetrazine–4-nitrobenzenesulfonamide (1/1) (III)

Crystal data

C12H8N6·C6H6N2O4S	Z = 4
Mr = 438.43	F(000) = 904
Triclinic, P1	Dx = 1.554 Mg m^−3
a = 10.8081 (3) Å	Cu Kα radiation, λ = 1.54184 Å
b = 13.0756 (4) Å	Cell parameters from 15754 reflections
c = 15.6720 (3) Å	θ = 3.1–76.3°
α = 100.946 (2)°	µ = 1.96 mm^−1
β = 107.154 (2)°	T = 293 K
γ = 110.429 (2)°	Plate, pink
V = 1874.13 (9) Å^3	0.22 × 0.17 × 0.11 mm

Data collection

Rigaku OD SuperNova (Dual, Cu at home/near) diffractometer with an Atlas detector	7852 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	7172 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.032
Detector resolution: 10.4052 pixels mm^-1	θmax = 76.5°, θmin = 3.1°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −16→16
Tmin = 0.755, Tmax = 1.000	l = −14→19
30142 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.154	w = 1/[σ^2(Fo^2) + (0.1143P)^2 + 0.6984P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
7852 reflections	Δρmax = 0.55 e Å^−3
575 parameters	Δρmin = −0.74 e Å^−3
0 restraints

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
S14A	0.58235 (4)	0.33635 (3)	−0.10282 (3)	0.00759 (12)
S14B	0.65019 (4)	0.37165 (3)	0.41984 (3)	0.00973 (12)
O15A	0.67429 (12)	0.28566 (10)	−0.12124 (9)	0.0132 (2)
O14A	0.55321 (13)	0.33598 (10)	−0.01902 (9)	0.0129 (2)
O14B	0.74939 (13)	0.32079 (11)	0.42468 (10)	0.0173 (3)
O15B	0.59122 (14)	0.37722 (11)	0.49087 (9)	0.0162 (3)
O11A	0.96989 (14)	0.86984 (11)	−0.07946 (10)	0.0187 (3)
N4A	0.91581 (14)	0.48759 (12)	0.12383 (10)	0.0113 (3)
N2A	0.76597 (15)	0.52038 (12)	0.20004 (10)	0.0098 (3)
N1B	0.61510 (15)	0.38461 (12)	0.68867 (10)	0.0097 (3)
O11B	0.86204 (16)	0.89893 (13)	0.39055 (13)	0.0294 (4)
N14A	0.43142 (14)	0.27279 (12)	−0.19120 (10)	0.0105 (3)
O12A	0.76725 (15)	0.87787 (11)	−0.10031 (12)	0.0241 (3)
N14B	0.51782 (15)	0.30319 (12)	0.32004 (10)	0.0114 (3)
N32B	0.77246 (15)	0.71228 (12)	0.68843 (10)	0.0123 (3)
N32A	0.83064 (15)	0.72860 (12)	0.16747 (10)	0.0119 (3)
O12B	1.06560 (16)	0.88982 (12)	0.42642 (13)	0.0303 (4)
N2B	0.67212 (14)	0.49448 (12)	0.69597 (10)	0.0100 (3)
N5A	0.86377 (15)	0.37819 (12)	0.11984 (10)	0.0120 (3)
N1A	0.71408 (15)	0.41077 (12)	0.19604 (10)	0.0104 (3)
N62B	0.47635 (16)	0.15338 (12)	0.64354 (11)	0.0141 (3)
N4B	0.87463 (15)	0.47662 (12)	0.67677 (10)	0.0119 (3)
N5B	0.81655 (15)	0.36579 (12)	0.66861 (10)	0.0123 (3)
N62A	0.59172 (17)	0.18414 (13)	0.17489 (11)	0.0148 (3)
N11A	0.84385 (16)	0.82688 (12)	−0.08919 (10)	0.0127 (3)
N11B	0.93774 (17)	0.84900 (13)	0.41202 (11)	0.0156 (3)
C3B	0.79533 (17)	0.53509 (14)	0.68258 (11)	0.0088 (3)
C13A	0.80501 (17)	0.53335 (14)	−0.08578 (11)	0.0099 (3)
H13A	0.858652	0.490880	−0.081667	0.012*
C6A	0.75921 (16)	0.34191 (14)	0.15162 (11)	0.0089 (3)
C6B	0.68354 (17)	0.32107 (13)	0.66745 (11)	0.0086 (3)
C3A	0.86050 (16)	0.55384 (13)	0.15969 (11)	0.0089 (3)
C31B	0.85190 (17)	0.65458 (14)	0.67942 (11)	0.0100 (3)
C14A	0.66290 (17)	0.48365 (13)	−0.09540 (11)	0.0085 (3)
C36A	1.04107 (17)	0.72481 (14)	0.14626 (12)	0.0122 (3)
H36A	1.096300	0.684810	0.141498	0.015*
C11A	0.78092 (17)	0.70726 (13)	−0.08927 (11)	0.0095 (3)
C13B	0.87767 (17)	0.55440 (14)	0.42236 (11)	0.0111 (3)
H13B	0.923171	0.505764	0.421955	0.013*
C15B	0.67148 (17)	0.58772 (15)	0.42663 (12)	0.0129 (3)
H15B	0.582419	0.561782	0.430906	0.015*
C31A	0.91304 (17)	0.67443 (13)	0.15821 (11)	0.0093 (3)
C61B	0.61078 (18)	0.19464 (14)	0.64698 (11)	0.0102 (3)
C11B	0.87071 (17)	0.73349 (14)	0.41895 (12)	0.0112 (3)
C14B	0.74122 (17)	0.51627 (14)	0.42423 (11)	0.0099 (3)
C12A	0.86552 (17)	0.64789 (14)	−0.08241 (11)	0.0105 (3)
H12A	0.960422	0.683672	−0.075711	0.013*
C61A	0.69273 (17)	0.21684 (13)	0.13963 (11)	0.0103 (3)
C16A	0.64039 (18)	0.65968 (14)	−0.09621 (12)	0.0128 (3)
H16A	0.587661	0.702857	−0.098676	0.015*
C36B	0.97882 (18)	0.70070 (15)	0.66540 (12)	0.0137 (3)
H36B	1.031280	0.658294	0.660259	0.016*
C15A	0.58098 (17)	0.54553 (14)	−0.09936 (12)	0.0131 (3)
H15A	0.486978	0.510732	−0.104079	0.016*
C35A	1.08407 (19)	0.83647 (15)	0.14166 (13)	0.0155 (3)
H35A	1.168747	0.872539	0.133637	0.019*
C12B	0.94519 (17)	0.66594 (14)	0.42112 (12)	0.0123 (3)
H12B	1.037345	0.694255	0.421730	0.015*
C33A	0.87433 (19)	0.83618 (15)	0.16279 (13)	0.0158 (3)
H33A	0.818221	0.874956	0.168972	0.019*
C35B	1.02523 (19)	0.81147 (16)	0.65926 (13)	0.0176 (4)
H35B	1.109496	0.844641	0.649994	0.021*
C66B	0.68031 (19)	0.12553 (15)	0.63161 (13)	0.0149 (3)
H66B	0.773482	0.157436	0.634306	0.018*
C33B	0.8195 (2)	0.81864 (15)	0.68232 (13)	0.0167 (3)
H33B	0.765909	0.859796	0.688533	0.020*
C34A	0.99867 (19)	0.89295 (14)	0.14923 (13)	0.0160 (3)
H34A	1.023867	0.967058	0.145333	0.019*
C16B	0.73579 (18)	0.69789 (15)	0.42259 (12)	0.0133 (3)
H16B	0.690074	0.746400	0.422319	0.016*
C65B	0.6062 (2)	0.00712 (15)	0.61206 (13)	0.0184 (4)
H65B	0.649202	−0.041681	0.601194	0.022*
C64B	0.4679 (2)	−0.03706 (15)	0.60900 (13)	0.0181 (4)
H64B	0.416614	−0.115638	0.596860	0.022*
C34B	0.9437 (2)	0.87158 (15)	0.66720 (13)	0.0181 (4)
H34B	0.971295	0.945414	0.662555	0.022*
C66A	0.73584 (19)	0.14113 (15)	0.09493 (13)	0.0163 (3)
H66A	0.805371	0.167148	0.070644	0.020*
C65A	0.6720 (2)	0.02545 (16)	0.08763 (15)	0.0214 (4)
H65A	0.698311	−0.027519	0.058367	0.026*
C63B	0.4074 (2)	0.03938 (15)	0.62460 (14)	0.0180 (4)
H63B	0.314003	0.009505	0.621696	0.022*
C63A	0.5315 (2)	0.07230 (16)	0.16664 (14)	0.0209 (4)
H63A	0.460835	0.048017	0.190346	0.025*
C64A	0.5689 (2)	−0.00954 (15)	0.12449 (15)	0.0229 (4)
H64A	0.525425	−0.086171	0.121206	0.027*
H14A	0.436 (3)	0.261 (2)	−0.248 (2)	0.025 (6)*
H14B	0.366 (3)	0.291 (3)	−0.185 (2)	0.031 (7)*
H14C	0.442 (3)	0.321 (3)	0.312 (2)	0.031 (7)*
H14D	0.544 (3)	0.291 (2)	0.273 (2)	0.027 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S14A	0.00681 (19)	0.00898 (19)	0.0089 (2)	0.00362 (14)	0.00425 (15)	0.00469 (14)
S14B	0.0097 (2)	0.0106 (2)	0.0082 (2)	0.00377 (15)	0.00196 (15)	0.00532 (15)
O15A	0.0111 (5)	0.0127 (5)	0.0217 (6)	0.0079 (4)	0.0099 (5)	0.0072 (5)
O14A	0.0152 (6)	0.0168 (6)	0.0111 (6)	0.0069 (5)	0.0082 (5)	0.0089 (5)
O14B	0.0136 (6)	0.0146 (6)	0.0247 (7)	0.0081 (5)	0.0044 (5)	0.0098 (5)
O15B	0.0198 (6)	0.0187 (6)	0.0093 (6)	0.0054 (5)	0.0067 (5)	0.0072 (5)
O11A	0.0125 (6)	0.0151 (6)	0.0283 (7)	0.0021 (5)	0.0100 (5)	0.0111 (5)
N4A	0.0094 (6)	0.0117 (6)	0.0137 (7)	0.0049 (5)	0.0045 (5)	0.0054 (5)
N2A	0.0104 (6)	0.0097 (6)	0.0091 (6)	0.0037 (5)	0.0037 (5)	0.0042 (5)
N1B	0.0104 (6)	0.0096 (6)	0.0087 (6)	0.0033 (5)	0.0039 (5)	0.0038 (5)
O11B	0.0249 (7)	0.0222 (7)	0.0557 (10)	0.0147 (6)	0.0211 (7)	0.0261 (7)
N14A	0.0076 (6)	0.0118 (6)	0.0108 (7)	0.0032 (5)	0.0036 (5)	0.0029 (5)
O12A	0.0212 (7)	0.0158 (6)	0.0445 (9)	0.0121 (5)	0.0158 (6)	0.0168 (6)
N14B	0.0101 (6)	0.0134 (6)	0.0085 (7)	0.0037 (5)	0.0031 (5)	0.0028 (5)
N32B	0.0144 (7)	0.0121 (6)	0.0119 (7)	0.0055 (5)	0.0055 (5)	0.0063 (5)
N32A	0.0113 (6)	0.0115 (6)	0.0130 (7)	0.0041 (5)	0.0046 (5)	0.0062 (5)
O12B	0.0172 (7)	0.0173 (6)	0.0603 (11)	0.0051 (5)	0.0223 (7)	0.0140 (7)
N2B	0.0101 (6)	0.0096 (6)	0.0093 (7)	0.0028 (5)	0.0038 (5)	0.0041 (5)
N5A	0.0096 (6)	0.0121 (6)	0.0155 (7)	0.0052 (5)	0.0047 (5)	0.0064 (5)
N1A	0.0117 (6)	0.0100 (6)	0.0102 (7)	0.0044 (5)	0.0046 (5)	0.0046 (5)
N62B	0.0152 (7)	0.0101 (6)	0.0183 (7)	0.0045 (5)	0.0090 (6)	0.0055 (5)
N4B	0.0094 (6)	0.0127 (6)	0.0134 (7)	0.0044 (5)	0.0036 (5)	0.0059 (5)
N5B	0.0104 (6)	0.0126 (6)	0.0141 (7)	0.0048 (5)	0.0042 (5)	0.0064 (5)
N62A	0.0189 (7)	0.0112 (6)	0.0139 (7)	0.0041 (5)	0.0076 (6)	0.0058 (5)
N11A	0.0132 (7)	0.0118 (6)	0.0136 (7)	0.0044 (5)	0.0062 (5)	0.0057 (5)
N11B	0.0149 (7)	0.0132 (7)	0.0202 (8)	0.0047 (6)	0.0097 (6)	0.0068 (6)
C3B	0.0077 (7)	0.0116 (7)	0.0043 (7)	0.0028 (6)	0.0005 (5)	0.0026 (5)
C13A	0.0105 (7)	0.0119 (7)	0.0094 (8)	0.0056 (6)	0.0046 (6)	0.0050 (6)
C6A	0.0075 (7)	0.0118 (7)	0.0057 (7)	0.0044 (6)	−0.0004 (5)	0.0035 (6)
C6B	0.0100 (7)	0.0117 (7)	0.0044 (7)	0.0050 (6)	0.0021 (5)	0.0040 (6)
C3A	0.0054 (6)	0.0118 (7)	0.0077 (7)	0.0029 (5)	0.0007 (5)	0.0039 (6)
C31B	0.0108 (7)	0.0114 (7)	0.0047 (7)	0.0028 (6)	0.0014 (6)	0.0028 (5)
C14A	0.0085 (7)	0.0110 (7)	0.0058 (7)	0.0036 (6)	0.0027 (5)	0.0036 (5)
C36A	0.0096 (7)	0.0131 (7)	0.0110 (8)	0.0028 (6)	0.0034 (6)	0.0031 (6)
C11A	0.0116 (7)	0.0086 (7)	0.0078 (7)	0.0027 (6)	0.0042 (6)	0.0045 (5)
C13B	0.0113 (7)	0.0147 (7)	0.0085 (7)	0.0075 (6)	0.0031 (6)	0.0037 (6)
C15B	0.0083 (7)	0.0163 (8)	0.0145 (8)	0.0048 (6)	0.0039 (6)	0.0075 (6)
C31A	0.0085 (7)	0.0110 (7)	0.0059 (7)	0.0029 (6)	0.0009 (6)	0.0031 (5)
C61B	0.0132 (7)	0.0112 (7)	0.0072 (7)	0.0057 (6)	0.0034 (6)	0.0051 (6)
C11B	0.0110 (7)	0.0107 (7)	0.0104 (8)	0.0029 (6)	0.0040 (6)	0.0041 (6)
C14B	0.0094 (7)	0.0115 (7)	0.0056 (7)	0.0030 (6)	0.0001 (6)	0.0034 (6)
C12A	0.0079 (7)	0.0131 (7)	0.0081 (7)	0.0023 (6)	0.0030 (6)	0.0032 (6)
C61A	0.0096 (7)	0.0109 (7)	0.0084 (7)	0.0040 (6)	0.0008 (6)	0.0043 (6)
C16A	0.0123 (7)	0.0128 (7)	0.0167 (8)	0.0073 (6)	0.0068 (6)	0.0065 (6)
C36B	0.0114 (7)	0.0153 (8)	0.0105 (8)	0.0025 (6)	0.0034 (6)	0.0037 (6)
C15A	0.0093 (7)	0.0135 (7)	0.0186 (9)	0.0047 (6)	0.0071 (6)	0.0077 (6)
C35A	0.0118 (7)	0.0145 (8)	0.0139 (8)	−0.0013 (6)	0.0057 (6)	0.0042 (6)
C12B	0.0083 (7)	0.0152 (7)	0.0115 (8)	0.0036 (6)	0.0035 (6)	0.0036 (6)
C33A	0.0178 (8)	0.0115 (7)	0.0206 (9)	0.0071 (6)	0.0083 (7)	0.0081 (6)
C35B	0.0154 (8)	0.0172 (8)	0.0141 (8)	−0.0006 (6)	0.0068 (7)	0.0055 (6)
C66B	0.0163 (8)	0.0161 (8)	0.0144 (8)	0.0096 (7)	0.0048 (6)	0.0061 (6)
C33B	0.0219 (9)	0.0124 (7)	0.0173 (9)	0.0075 (6)	0.0081 (7)	0.0073 (6)
C34A	0.0189 (8)	0.0092 (7)	0.0159 (8)	0.0013 (6)	0.0059 (7)	0.0062 (6)
C16B	0.0116 (7)	0.0140 (7)	0.0156 (8)	0.0067 (6)	0.0044 (6)	0.0067 (6)
C65B	0.0262 (9)	0.0146 (8)	0.0169 (9)	0.0134 (7)	0.0056 (7)	0.0060 (7)
C64B	0.0273 (9)	0.0093 (7)	0.0164 (9)	0.0069 (7)	0.0067 (7)	0.0067 (6)
C34B	0.0254 (9)	0.0098 (7)	0.0164 (9)	0.0025 (7)	0.0092 (7)	0.0068 (6)
C66A	0.0144 (8)	0.0144 (8)	0.0197 (9)	0.0073 (6)	0.0056 (7)	0.0045 (7)
C65A	0.0237 (9)	0.0135 (8)	0.0241 (10)	0.0106 (7)	0.0041 (7)	0.0036 (7)
C63B	0.0184 (8)	0.0114 (8)	0.0232 (9)	0.0028 (6)	0.0105 (7)	0.0069 (7)
C63A	0.0280 (10)	0.0138 (8)	0.0195 (9)	0.0039 (7)	0.0120 (8)	0.0085 (7)
C64A	0.0314 (10)	0.0093 (7)	0.0237 (10)	0.0058 (7)	0.0068 (8)	0.0087 (7)

Geometric parameters (Å, º)

S14A—O15A	1.4375 (11)	C36A—H36A	0.9300
S14A—O14A	1.4385 (12)	C36A—C31A	1.395 (2)
S14A—N14A	1.5981 (14)	C36A—C35A	1.392 (2)
S14A—C14A	1.7794 (16)	C11A—C12A	1.385 (2)
S14B—O14B	1.4376 (12)	C11A—C16A	1.387 (2)
S14B—O15B	1.4391 (13)	C13B—H13B	0.9300
S14B—N14B	1.5965 (14)	C13B—C14B	1.394 (2)
S14B—C14B	1.7778 (16)	C13B—C12B	1.391 (2)
O11A—N11A	1.227 (2)	C15B—H15B	0.9300
N4A—N5A	1.3229 (19)	C15B—C14B	1.392 (2)
N4A—C3A	1.341 (2)	C15B—C16B	1.387 (2)
N2A—N1A	1.3254 (19)	C61B—C66B	1.392 (2)
N2A—C3A	1.345 (2)	C11B—C12B	1.386 (2)
N1B—N2B	1.3171 (19)	C11B—C16B	1.390 (2)
N1B—C6B	1.348 (2)	C12A—H12A	0.9300
O11B—N11B	1.226 (2)	C61A—C66A	1.392 (2)
N14A—H14A	0.90 (3)	C16A—H16A	0.9300
N14A—H14B	0.85 (3)	C16A—C15A	1.388 (2)
O12A—N11A	1.227 (2)	C36B—H36B	0.9300
N14B—H14C	0.90 (3)	C36B—C35B	1.390 (2)
N14B—H14D	0.87 (3)	C15A—H15A	0.9300
N32B—C31B	1.345 (2)	C35A—H35A	0.9300
N32B—C33B	1.337 (2)	C35A—C34A	1.385 (3)
N32A—C31A	1.339 (2)	C12B—H12B	0.9300
N32A—C33A	1.343 (2)	C33A—H33A	0.9300
O12B—N11B	1.225 (2)	C33A—C34A	1.391 (2)
N2B—C3B	1.346 (2)	C35B—H35B	0.9300
N5A—C6A	1.341 (2)	C35B—C34B	1.386 (3)
N1A—C6A	1.342 (2)	C66B—H66B	0.9300
N62B—C61B	1.342 (2)	C66B—C65B	1.394 (2)
N62B—C63B	1.338 (2)	C33B—H33B	0.9300
N4B—N5B	1.326 (2)	C33B—C34B	1.393 (3)
N4B—C3B	1.343 (2)	C34A—H34A	0.9300
N5B—C6B	1.343 (2)	C16B—H16B	0.9300
N62A—C61A	1.342 (2)	C65B—H65B	0.9300
N62A—C63A	1.339 (2)	C65B—C64B	1.384 (3)
N11A—C11A	1.4714 (19)	C64B—H64B	0.9300
N11B—C11B	1.471 (2)	C64B—C63B	1.394 (3)
C3B—C31B	1.482 (2)	C34B—H34B	0.9300
C13A—H13A	0.9300	C66A—H66A	0.9300
C13A—C14A	1.391 (2)	C66A—C65A	1.391 (2)
C13A—C12A	1.393 (2)	C65A—H65A	0.9300
C6A—C61A	1.486 (2)	C65A—C64A	1.382 (3)
C6B—C61B	1.482 (2)	C63B—H63B	0.9300
C3A—C31A	1.485 (2)	C63A—H63A	0.9300
C31B—C36B	1.394 (2)	C63A—C64A	1.391 (3)
C14A—C15A	1.389 (2)	C64A—H64A	0.9300
O15A—S14A—O14A	119.13 (7)	N62B—C61B—C6B	115.80 (14)
O15A—S14A—N14A	108.06 (7)	N62B—C61B—C66B	123.59 (15)
O15A—S14A—C14A	107.09 (7)	C66B—C61B—C6B	120.61 (15)
O14A—S14A—N14A	107.37 (7)	C12B—C11B—N11B	118.26 (14)
O14A—S14A—C14A	106.44 (7)	C12B—C11B—C16B	123.59 (15)
N14A—S14A—C14A	108.37 (7)	C16B—C11B—N11B	118.14 (15)
O14B—S14B—O15B	119.57 (8)	C13B—C14B—S14B	119.76 (12)
O14B—S14B—N14B	108.08 (8)	C15B—C14B—S14B	118.56 (12)
O14B—S14B—C14B	106.81 (8)	C15B—C14B—C13B	121.66 (15)
O15B—S14B—N14B	106.98 (8)	C13A—C12A—H12A	120.8
O15B—S14B—C14B	106.53 (7)	C11A—C12A—C13A	118.40 (14)
N14B—S14B—C14B	108.49 (7)	C11A—C12A—H12A	120.8
N5A—N4A—C3A	117.58 (13)	N62A—C61A—C6A	115.62 (14)
N1A—N2A—C3A	117.24 (13)	N62A—C61A—C66A	123.63 (15)
N2B—N1B—C6B	117.64 (13)	C66A—C61A—C6A	120.75 (15)
S14A—N14A—H14A	115.6 (18)	C11A—C16A—H16A	121.1
S14A—N14A—H14B	115 (2)	C11A—C16A—C15A	117.84 (15)
H14A—N14A—H14B	117 (3)	C15A—C16A—H16A	121.1
S14B—N14B—H14C	116.3 (19)	C31B—C36B—H36B	120.7
S14B—N14B—H14D	112.9 (19)	C35B—C36B—C31B	118.55 (16)
H14C—N14B—H14D	119 (3)	C35B—C36B—H36B	120.7
C33B—N32B—C31B	116.90 (15)	C14A—C15A—H15A	120.2
C31A—N32A—C33A	117.03 (14)	C16A—C15A—C14A	119.54 (14)
N1B—N2B—C3B	117.41 (14)	C16A—C15A—H15A	120.2
N4A—N5A—C6A	117.43 (14)	C36A—C35A—H35A	120.5
N2A—N1A—C6A	117.52 (13)	C34A—C35A—C36A	118.92 (15)
C63B—N62B—C61B	117.23 (15)	C34A—C35A—H35A	120.5
N5B—N4B—C3B	117.40 (13)	C13B—C12B—H12B	121.1
N4B—N5B—C6B	117.44 (14)	C11B—C12B—C13B	117.88 (15)
C63A—N62A—C61A	117.07 (16)	C11B—C12B—H12B	121.1
O11A—N11A—C11A	118.16 (14)	N32A—C33A—H33A	118.1
O12A—N11A—O11A	123.38 (14)	N32A—C33A—C34A	123.77 (16)
O12A—N11A—C11A	118.46 (14)	C34A—C33A—H33A	118.1
O11B—N11B—C11B	118.19 (15)	C36B—C35B—H35B	120.6
O12B—N11B—O11B	123.23 (15)	C34B—C35B—C36B	118.83 (16)
O12B—N11B—C11B	118.57 (15)	C34B—C35B—H35B	120.6
N2B—C3B—C31B	118.07 (14)	C61B—C66B—H66B	121.0
N4B—C3B—N2B	124.27 (14)	C61B—C66B—C65B	118.04 (16)
N4B—C3B—C31B	117.57 (14)	C65B—C66B—H66B	121.0
C14A—C13A—H13A	120.6	N32B—C33B—H33B	118.0
C14A—C13A—C12A	118.76 (14)	N32B—C33B—C34B	124.01 (17)
C12A—C13A—H13A	120.6	C34B—C33B—H33B	118.0
N5A—C6A—N1A	124.77 (14)	C35A—C34A—C33A	118.41 (15)
N5A—C6A—C61A	117.19 (14)	C35A—C34A—H34A	120.8
N1A—C6A—C61A	118.00 (14)	C33A—C34A—H34A	120.8
N1B—C6B—C61B	117.91 (14)	C15B—C16B—C11B	117.88 (15)
N5B—C6B—N1B	124.08 (14)	C15B—C16B—H16B	121.1
N5B—C6B—C61B	117.91 (14)	C11B—C16B—H16B	121.1
N4A—C3A—N2A	124.76 (14)	C66B—C65B—H65B	120.4
N4A—C3A—C31A	117.12 (14)	C64B—C65B—C66B	119.28 (16)
N2A—C3A—C31A	118.06 (14)	C64B—C65B—H65B	120.4
N32B—C31B—C3B	116.23 (14)	C65B—C64B—H64B	120.9
N32B—C31B—C36B	123.37 (15)	C65B—C64B—C63B	118.21 (16)
C36B—C31B—C3B	120.38 (15)	C63B—C64B—H64B	120.9
C13A—C14A—S14A	119.42 (12)	C35B—C34B—C33B	118.34 (16)
C15A—C14A—S14A	118.54 (12)	C35B—C34B—H34B	120.8
C15A—C14A—C13A	122.04 (14)	C33B—C34B—H34B	120.8
C31A—C36A—H36A	120.8	C61A—C66A—H66A	120.9
C35A—C36A—H36A	120.8	C65A—C66A—C61A	118.15 (16)
C35A—C36A—C31A	118.34 (15)	C65A—C66A—H66A	120.9
C12A—C11A—N11A	118.11 (14)	C66A—C65A—H65A	120.5
C12A—C11A—C16A	123.36 (14)	C64A—C65A—C66A	119.01 (17)
C16A—C11A—N11A	118.53 (14)	C64A—C65A—H65A	120.5
C14B—C13B—H13B	120.3	N62B—C63B—C64B	123.65 (17)
C12B—C13B—H13B	120.3	N62B—C63B—H63B	118.2
C12B—C13B—C14B	119.36 (14)	C64B—C63B—H63B	118.2
C14B—C15B—H15B	120.2	N62A—C63A—H63A	118.2
C16B—C15B—H15B	120.2	N62A—C63A—C64A	123.53 (18)
C16B—C15B—C14B	119.51 (15)	C64A—C63A—H63A	118.2
N32A—C31A—C3A	116.47 (14)	C65A—C64A—C63A	118.59 (17)
N32A—C31A—C36A	123.51 (15)	C65A—C64A—H64A	120.7
C36A—C31A—C3A	120.01 (14)	C63A—C64A—H64A	120.7
S14A—C14A—C15A—C16A	−178.31 (13)	N5B—N4B—C3B—C31B	−172.39 (13)
O15A—S14A—C14A—C13A	−14.45 (15)	N5B—C6B—C61B—N62B	−177.91 (15)
O15A—S14A—C14A—C15A	165.63 (13)	N5B—C6B—C61B—C66B	1.4 (2)
O14A—S14A—C14A—C13A	113.99 (13)	N62A—C61A—C66A—C65A	−0.9 (3)
O14A—S14A—C14A—C15A	−65.93 (14)	N62A—C63A—C64A—C65A	−1.1 (3)
O14B—S14B—C14B—C13B	5.86 (16)	N11A—C11A—C12A—C13A	−177.79 (14)
O14B—S14B—C14B—C15B	−176.04 (13)	N11A—C11A—C16A—C15A	177.90 (14)
O15B—S14B—C14B—C13B	134.71 (13)	N11B—C11B—C12B—C13B	−176.49 (14)
O15B—S14B—C14B—C15B	−47.18 (15)	N11B—C11B—C16B—C15B	178.35 (15)
O11A—N11A—C11A—C12A	−2.7 (2)	C3B—N4B—N5B—C6B	−0.5 (2)
O11A—N11A—C11A—C16A	177.31 (15)	C3B—C31B—C36B—C35B	177.56 (14)
N4A—N5A—C6A—N1A	−7.3 (2)	C13A—C14A—C15A—C16A	1.8 (3)
N4A—N5A—C6A—C61A	175.03 (13)	C6A—C61A—C66A—C65A	178.60 (15)
N4A—C3A—C31A—N32A	161.06 (15)	C6B—N1B—N2B—C3B	−0.7 (2)
N4A—C3A—C31A—C36A	−18.1 (2)	C6B—C61B—C66B—C65B	−179.59 (15)
N2A—N1A—C6A—N5A	7.4 (2)	C3A—N4A—N5A—C6A	0.3 (2)
N2A—N1A—C6A—C61A	−174.98 (13)	C3A—N2A—N1A—C6A	−0.4 (2)
N2A—C3A—C31A—N32A	−21.6 (2)	C31B—N32B—C33B—C34B	0.1 (3)
N2A—C3A—C31A—C36A	159.30 (15)	C31B—C36B—C35B—C34B	−0.1 (3)
N1B—N2B—C3B—N4B	−10.7 (2)	C14A—C13A—C12A—C11A	−0.3 (2)
N1B—N2B—C3B—C31B	172.99 (13)	C36A—C35A—C34A—C33A	1.1 (3)
N1B—C6B—C61B—N62B	5.6 (2)	C11A—C16A—C15A—C14A	0.1 (2)
N1B—C6B—C61B—C66B	−175.14 (15)	C31A—N32A—C33A—C34A	−0.1 (3)
O11B—N11B—C11B—C12B	165.15 (17)	C31A—C36A—C35A—C34A	0.1 (2)
O11B—N11B—C11B—C16B	−14.6 (2)	C61B—N62B—C63B—C64B	0.3 (3)
N14A—S14A—C14A—C13A	−130.80 (13)	C61B—C66B—C65B—C64B	−0.2 (3)
N14A—S14A—C14A—C15A	49.28 (15)	C14B—C13B—C12B—C11B	−1.9 (2)
O12A—N11A—C11A—C12A	176.17 (16)	C14B—C15B—C16B—C11B	−1.8 (2)
O12A—N11A—C11A—C16A	−3.8 (2)	C12A—C13A—C14A—S14A	178.43 (12)
N14B—S14B—C14B—C13B	−110.43 (14)	C12A—C13A—C14A—C15A	−1.6 (2)
N14B—S14B—C14B—C15B	67.68 (15)	C12A—C11A—C16A—C15A	−2.1 (3)
N32B—C31B—C36B—C35B	−0.8 (3)	C61A—N62A—C63A—C64A	0.4 (3)
N32B—C33B—C34B—C35B	−0.9 (3)	C61A—C66A—C65A—C64A	0.2 (3)
N32A—C33A—C34A—C35A	−1.1 (3)	C16A—C11A—C12A—C13A	2.2 (2)
O12B—N11B—C11B—C12B	−13.7 (2)	C36B—C35B—C34B—C33B	0.9 (3)
O12B—N11B—C11B—C16B	166.57 (17)	C35A—C36A—C31A—N32A	−1.4 (2)
N2B—N1B—C6B—N5B	11.4 (2)	C35A—C36A—C31A—C3A	177.61 (14)
N2B—N1B—C6B—C61B	−172.27 (13)	C12B—C13B—C14B—S14B	176.85 (12)
N2B—C3B—C31B—N32B	−1.3 (2)	C12B—C13B—C14B—C15B	−1.2 (2)
N2B—C3B—C31B—C36B	−179.78 (15)	C12B—C11B—C16B—C15B	−1.4 (3)
N5A—N4A—C3A—N2A	6.6 (2)	C33A—N32A—C31A—C3A	−177.64 (14)
N5A—N4A—C3A—C31A	−176.20 (13)	C33A—N32A—C31A—C36A	1.4 (2)
N5A—C6A—C61A—N62A	177.96 (15)	C66B—C65B—C64B—C63B	0.8 (3)
N5A—C6A—C61A—C66A	−1.6 (2)	C33B—N32B—C31B—C3B	−177.67 (14)
N1A—N2A—C3A—N4A	−6.6 (2)	C33B—N32B—C31B—C36B	0.7 (2)
N1A—N2A—C3A—C31A	176.30 (13)	C16B—C15B—C14B—S14B	−174.97 (13)
N1A—C6A—C61A—N62A	0.1 (2)	C16B—C15B—C14B—C13B	3.1 (3)
N1A—C6A—C61A—C66A	−179.41 (16)	C16B—C11B—C12B—C13B	3.2 (3)
N62B—C61B—C66B—C65B	−0.3 (3)	C65B—C64B—C63B—N62B	−0.8 (3)
N4B—N5B—C6B—N1B	−10.8 (2)	C66A—C65A—C64A—C63A	0.8 (3)
N4B—N5B—C6B—C61B	172.88 (14)	C63B—N62B—C61B—C6B	179.59 (15)
N4B—C3B—C31B—N32B	−177.93 (14)	C63B—N62B—C61B—C66B	0.3 (3)
N4B—C3B—C31B—C36B	3.6 (2)	C63A—N62A—C61A—C6A	−178.90 (15)
N5B—N4B—C3B—N2B	11.2 (2)	C63A—N62A—C61A—C66A	0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13A—H13A···N4A^i	0.93	2.65	3.333 (2)	131
C36A—H36A···O15A^i	0.93	2.50	3.2592 (19)	139
C15B—H15B···N2B^ii	0.93	2.62	3.295 (2)	130
C12A—H12A···N5A^i	0.93	2.53	3.264 (2)	137
C15A—H15A···N2A^iii	0.93	2.54	3.321 (2)	141
C12B—H12B···N5B^iv	0.93	2.62	3.383 (2)	139
C66B—H66B···O12B^iv	0.93	2.41	3.193 (2)	142
C34A—H34A···O11A^v	0.93	2.53	3.421 (2)	161
C16B—H16B···N62B^ii	0.93	2.66	3.548 (2)	160
C64B—H64B···O14B^vi	0.93	2.54	3.464 (2)	171
C34B—H34B···O11B^vii	0.93	2.65	3.462 (2)	146
C66A—H66A···O11A^i	0.93	2.61	3.310 (2)	133
C63B—H63B···O11B^ii	0.93	2.56	3.239 (2)	130
C64A—H64A···S14A^viii	0.93	2.99	3.9106 (18)	172
N14A—H14A···N1B^ix	0.90 (3)	2.62 (3)	3.2934 (19)	132 (2)
N14A—H14A···N62B^ix	0.90 (3)	2.24 (3)	3.019 (2)	146 (2)
N14A—H14B···N32A^iii	0.85 (3)	2.15 (3)	2.958 (2)	158 (3)
N14B—H14C···N32B^ii	0.90 (3)	2.21 (3)	3.034 (2)	152 (3)
N14B—H14D···N1A	0.87 (3)	2.70 (3)	3.412 (2)	140 (2)
N14B—H14D···N62A	0.87 (3)	2.18 (3)	2.972 (2)	152 (2)

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z; (iv) −x+2, −y+1, −z+1; (v) −x+2, −y+2, −z; (vi) −x+1, −y, −z+1; (vii) −x+2, −y+2, −z+1; (viii) −x+1, −y, −z; (ix) x, y, z−1.