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In the title compound, C24H18N10O, the tetrazine ring adopts a boat conformation. The structure is stabilized by strong intramolecular and weak intermolecular N—H...N hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801020049/ci6079sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801020049/ci6079Isup2.hkl
Contains datablock I

CCDC reference: 164867

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.056
  • wR factor = 0.086
  • Data-to-parameter ratio = 11.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Red Alert Alert Level A:
DIFF_020 Alert A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards.
1 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
0 Alert Level C = Please check

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.

3,6-di-2-pyridyl-1-H-4-(1,4-di-2-pyridyl-2,3-diaze-4-carbonyl)-1-yl- 1,2,4,5-tetrazine top
Crystal data top
C24H18N10OZ = 2
Mr = 462.48F(000) = 480
Triclinic, P1Dx = 1.426 Mg m3
a = 7.949 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.540 (7) ÅCell parameters from 4426 reflections
c = 12.118 (7) Åθ = 2.4–25.0°
α = 83.200 (11)°µ = 0.10 mm1
β = 85.971 (12)°T = 293 K
γ = 77.557 (11)°Prism, orange
V = 1076.8 (11) Å30.30 × 0.25 × 0.20 mm
Data collection top
Bruker SMART 1000
diffractometer
2474 reflections with I > 2σ(I)
ω scansRint = 0.052
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1997)
θmax = 25.0°
Tmin = 0.972, Tmax = 0.981h = 89
4478 measured reflectionsk = 1313
3752 independent reflectionsl = 714
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.056 w = 1/[σ2(Fo2) + (0.005P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086(Δ/σ)max = 0.008
S = 0.88Δρmax = 0.17 e Å3
3752 reflectionsΔρmin = 0.17 e Å3
324 parameters
Special details top

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. Full-matrix

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2283 (3)0.8551 (2)0.36396 (17)0.0493 (7)
N10.5403 (4)0.8270 (3)0.5674 (2)0.0504 (9)
N20.7841 (4)0.5854 (2)0.0521 (2)0.0402 (8)
N31.2522 (4)0.5890 (3)0.4852 (2)0.0459 (9)
N40.7594 (4)0.9077 (3)0.0661 (2)0.0521 (9)
N50.8204 (4)0.6993 (2)0.2322 (2)0.0345 (8)
N60.8597 (4)0.6899 (3)0.3460 (2)0.0380 (8)
N71.1443 (4)0.6330 (3)0.2762 (2)0.0428 (8)
H71.2536 (18)0.629 (3)0.294 (2)0.048 (12)*
N81.1060 (4)0.7091 (3)0.1759 (2)0.0421 (8)
N90.5108 (4)0.7225 (2)0.2625 (2)0.0390 (8)
N100.5166 (4)0.7678 (3)0.3631 (2)0.0431 (9)
H100.614 (2)0.766 (3)0.397 (2)0.054 (13)*
C11.3134 (5)0.5693 (3)0.5886 (3)0.0530 (11)
H11.43030.53740.59640.064*
C21.2123 (6)0.5938 (3)0.6822 (3)0.0568 (12)
H21.26020.58120.75160.068*
C31.0394 (6)0.6372 (4)0.6723 (3)0.0575 (12)
H30.96760.65130.73540.069*
C40.9712 (5)0.6603 (3)0.5676 (3)0.0520 (11)
H40.85450.69160.55830.062*
C51.0853 (5)0.6344 (3)0.4777 (3)0.0371 (10)
C61.0189 (5)0.6554 (3)0.3626 (3)0.0369 (10)
C70.9463 (5)0.7364 (3)0.1557 (3)0.0318 (9)
C80.8946 (5)0.8195 (3)0.0548 (3)0.0381 (10)
C90.9952 (5)0.8068 (4)0.0425 (3)0.0623 (13)
H91.08970.74370.04700.075*
C100.9519 (6)0.8903 (5)0.1333 (3)0.0706 (14)
H10A1.01490.88290.20060.085*
C110.8170 (7)0.9826 (4)0.1228 (3)0.0733 (15)
H110.78851.04210.18120.088*
C120.7232 (6)0.9860 (4)0.0234 (4)0.0740 (14)
H120.62701.04770.01810.089*
C130.7754 (5)0.5528 (3)0.0498 (3)0.0454 (11)
H130.87160.50260.07890.054*
C140.6339 (5)0.5887 (3)0.1136 (3)0.0487 (11)
H140.63600.56570.18480.058*
C150.4882 (5)0.6599 (3)0.0696 (3)0.0512 (11)
H150.38940.68510.11010.061*
C160.4923 (4)0.6928 (3)0.0358 (3)0.0388 (10)
H160.39530.73940.06800.047*
C170.6416 (5)0.6559 (3)0.0926 (3)0.0310 (9)
C180.6535 (5)0.6968 (3)0.2050 (3)0.0336 (9)
C190.3687 (5)0.8305 (3)0.4076 (3)0.0401 (10)
C200.3867 (5)0.8703 (3)0.5199 (3)0.0387 (10)
C210.2542 (5)0.9475 (3)0.5661 (3)0.0532 (12)
H210.15100.97490.53050.064*
C220.2774 (6)0.9844 (4)0.6680 (3)0.0653 (14)
H220.18981.03750.70190.078*
C230.4312 (7)0.9414 (4)0.7178 (3)0.0675 (14)
H230.44820.96380.78670.081*
C240.5592 (6)0.8655 (4)0.6656 (3)0.0674 (14)
H240.66410.83910.69930.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0435 (19)0.0626 (19)0.0394 (16)0.0068 (16)0.0033 (13)0.0025 (13)
N10.060 (3)0.060 (2)0.032 (2)0.012 (2)0.0011 (17)0.0101 (17)
N20.037 (2)0.049 (2)0.0304 (19)0.0017 (17)0.0008 (15)0.0083 (16)
N30.042 (2)0.056 (2)0.036 (2)0.0047 (18)0.0120 (16)0.0052 (16)
N40.060 (2)0.041 (2)0.045 (2)0.0055 (19)0.0060 (17)0.0048 (17)
N50.036 (2)0.052 (2)0.0168 (17)0.0111 (17)0.0026 (14)0.0024 (14)
N60.037 (2)0.055 (2)0.0212 (17)0.0080 (18)0.0065 (14)0.0015 (14)
N70.035 (2)0.063 (2)0.0247 (19)0.000 (2)0.0013 (16)0.0008 (16)
N80.041 (2)0.059 (2)0.0239 (18)0.0077 (18)0.0012 (15)0.0011 (15)
N90.039 (2)0.054 (2)0.0242 (18)0.0100 (17)0.0015 (14)0.0061 (15)
N100.037 (2)0.065 (2)0.027 (2)0.007 (2)0.0012 (16)0.0144 (16)
C10.050 (3)0.061 (3)0.047 (3)0.010 (2)0.017 (2)0.006 (2)
C20.086 (4)0.058 (3)0.029 (3)0.019 (3)0.015 (2)0.003 (2)
C30.064 (3)0.076 (3)0.032 (3)0.014 (3)0.003 (2)0.004 (2)
C40.048 (3)0.070 (3)0.034 (3)0.003 (2)0.009 (2)0.004 (2)
C50.045 (3)0.043 (2)0.024 (2)0.012 (2)0.0045 (19)0.0020 (18)
C60.042 (3)0.040 (2)0.027 (2)0.008 (2)0.0030 (19)0.0013 (17)
C70.027 (2)0.040 (2)0.029 (2)0.005 (2)0.0029 (17)0.0096 (17)
C80.038 (3)0.046 (3)0.030 (2)0.008 (2)0.0035 (18)0.0044 (19)
C90.062 (3)0.090 (3)0.033 (3)0.015 (3)0.009 (2)0.006 (2)
C100.090 (4)0.094 (4)0.032 (3)0.042 (3)0.004 (3)0.010 (3)
C110.100 (4)0.070 (4)0.053 (3)0.035 (3)0.021 (3)0.024 (3)
C120.088 (4)0.045 (3)0.081 (4)0.004 (3)0.020 (3)0.017 (3)
C130.047 (3)0.048 (3)0.042 (3)0.006 (2)0.002 (2)0.016 (2)
C140.052 (3)0.062 (3)0.034 (2)0.009 (2)0.005 (2)0.017 (2)
C150.043 (3)0.072 (3)0.036 (2)0.004 (2)0.0082 (19)0.009 (2)
C160.032 (2)0.044 (3)0.038 (2)0.001 (2)0.0007 (18)0.0106 (19)
C170.033 (2)0.035 (2)0.025 (2)0.007 (2)0.0000 (17)0.0039 (17)
C180.031 (2)0.042 (2)0.026 (2)0.007 (2)0.0043 (17)0.0042 (17)
C190.039 (3)0.044 (3)0.036 (2)0.007 (2)0.000 (2)0.0026 (19)
C200.049 (3)0.035 (2)0.031 (2)0.010 (2)0.006 (2)0.0043 (18)
C210.054 (3)0.053 (3)0.049 (3)0.001 (2)0.007 (2)0.011 (2)
C220.086 (4)0.058 (3)0.053 (3)0.019 (3)0.024 (3)0.022 (3)
C230.100 (4)0.077 (4)0.030 (3)0.026 (3)0.007 (3)0.017 (2)
C240.079 (4)0.082 (4)0.039 (3)0.009 (3)0.003 (2)0.017 (2)
Geometric parameters (Å, º) top
O1—C191.232 (4)C5—C61.500 (4)
N1—C241.347 (4)C7—C81.486 (4)
N1—C201.356 (4)C8—C91.382 (4)
N2—C131.343 (3)C9—C101.384 (5)
N2—C171.344 (4)C9—H90.93
N3—C51.322 (4)C10—C111.349 (5)
N3—C11.353 (4)C10—H10A0.93
N4—C81.323 (4)C11—C121.371 (5)
N4—C121.333 (4)C11—H110.93
N5—C181.396 (4)C12—H120.93
N5—C71.416 (4)C13—C141.371 (4)
N5—N61.422 (3)C13—H130.93
N6—C61.265 (4)C14—C151.382 (4)
N7—C61.401 (4)C14—H140.93
N7—N81.423 (4)C15—C161.379 (4)
N7—H70.899 (10)C15—H150.93
N8—C71.274 (4)C16—C171.375 (4)
N9—C181.285 (4)C16—H160.93
N9—N101.389 (3)C17—C181.509 (4)
N10—C191.355 (4)C19—C201.512 (4)
N10—H100.896 (10)C20—C211.360 (4)
C1—C21.364 (4)C21—C221.389 (5)
C1—H10.93C21—H210.93
C2—C31.366 (5)C22—C231.370 (5)
C2—H20.93C22—H220.93
C3—C41.388 (4)C23—C241.363 (5)
C3—H30.93C23—H230.93
C4—C51.386 (4)C24—H240.93
C4—H40.93
C24—N1—C20116.5 (3)C11—C10—H10A120.4
C13—N2—C17116.3 (3)C9—C10—H10A120.4
C5—N3—C1116.5 (3)C10—C11—C12118.1 (4)
C8—N4—C12115.9 (3)C10—C11—H11121.0
C18—N5—C7124.3 (3)C12—C11—H11121.0
C18—N5—N6119.3 (3)N4—C12—C11125.0 (4)
C7—N5—N6114.9 (3)N4—C12—H12117.5
C6—N6—N5113.5 (3)C11—C12—H12117.5
C6—N7—N8114.1 (3)N2—C13—C14124.3 (3)
C6—N7—H7115.8 (19)N2—C13—H13117.9
N8—N7—H7110 (2)C14—C13—H13117.9
C7—N8—N7114.1 (3)C13—C14—C15118.3 (3)
C18—N9—N10117.2 (3)C13—C14—H14120.8
C19—N10—N9118.4 (3)C15—C14—H14120.8
C19—N10—H10116 (2)C16—C15—C14118.6 (3)
N9—N10—H10125 (2)C16—C15—H15120.7
N3—C1—C2123.3 (4)C14—C15—H15120.7
N3—C1—H1118.3C17—C16—C15119.2 (3)
C2—C1—H1118.3C17—C16—H16120.4
C1—C2—C3118.8 (4)C15—C16—H16120.4
C1—C2—H2120.6N2—C17—C16123.2 (3)
C3—C2—H2120.6N2—C17—C18116.3 (3)
C2—C3—C4119.8 (4)C16—C17—C18120.4 (3)
C2—C3—H3120.1N9—C18—N5129.3 (3)
C4—C3—H3120.1N9—C18—C17116.1 (3)
C5—C4—C3116.9 (4)N5—C18—C17114.5 (3)
C5—C4—H4121.6O1—C19—N10125.1 (3)
C3—C4—H4121.6O1—C19—C20120.6 (3)
N3—C5—C4124.6 (3)N10—C19—C20114.3 (3)
N3—C5—C6116.0 (3)N1—C20—C21123.9 (4)
C4—C5—C6119.4 (4)N1—C20—C19116.3 (3)
N6—C6—N7122.8 (3)C21—C20—C19119.8 (4)
N6—C6—C5121.6 (3)C20—C21—C22118.1 (4)
N7—C6—C5115.6 (3)C20—C21—H21120.9
N8—C7—N5121.4 (3)C22—C21—H21120.9
N8—C7—C8117.5 (3)C23—C22—C21119.0 (4)
N5—C7—C8120.7 (3)C23—C22—H22120.5
N4—C8—C9123.5 (3)C21—C22—H22120.5
N4—C8—C7117.0 (3)C24—C23—C22119.5 (4)
C9—C8—C7119.3 (4)C24—C23—H23120.2
C8—C9—C10118.3 (4)C22—C23—H23120.2
C8—C9—H9120.8N1—C24—C23122.9 (4)
C10—C9—H9120.8N1—C24—H24118.5
C11—C10—C9119.2 (4)C23—C24—H24118.5
 

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