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The title compound, C28H18Cl2N4O4, was prepared by the reaction of phenyl chloro­formate and 3,6-bis(4-chloro­phenyl)-1,4-di­hydro-1,2,4,5-tetrazine. The structural identity, confirmed by crystal structure determination, revealed a re-arrangement, resulting in formation of the 1,2-di­hydro­tetrazine derivative from the starting materials. The central tetrazine ring adopts a twist conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013607/cv6503sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013607/cv6503Isup2.hkl
Contains datablock I

CCDC reference: 255704

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.035
  • wR factor = 0.107
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C16 -C21 1.37 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C28 H18 Cl2 N4 O4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 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 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Diphenyl 3,6-bis(4-chlorophenyl)-1,2-dihydro-1,2,4,5-tetrazine-1,2-dicarboxylate top
Crystal data top
C28H18Cl2N4O4Z = 2
Mr = 545.36F(000) = 560
Triclinic, P1Dx = 1.402 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.357 (4) ÅCell parameters from 25 reflections
b = 12.439 (2) Åθ = 9.9–13.4°
c = 13.103 (3) ŵ = 0.29 mm1
α = 116.800 (17)°T = 295 K
β = 108.38 (2)°Prismatic, colorless
γ = 80.91 (2)°0.30 × 0.20 × 0.15 mm
V = 1291.6 (7) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
2615 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.016
Graphite monochromatorθmax = 25.2°, θmin = 1.8°
ω/2θ scansh = 111
Absorption correction: empirical (using intensity measurements)
(North et al., 1968)
k = 1414
Tmin = 0.917, Tmax = 0.958l = 1515
5540 measured reflections3 standard reflections every 60 min
4615 independent reflections intensity decay: <1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.107 w = 1/[σ2(Fo2) + (0.0502P)2 + 0.1993P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4615 reflectionsΔρmax = 0.19 e Å3
344 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0057 (12)
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. 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 (Å2) top
xyzUiso*/Ueq
Cl10.98772 (9)0.10935 (7)0.24279 (8)0.0875 (3)
Cl20.31192 (9)0.48131 (7)0.10625 (7)0.0840 (3)
O10.1383 (2)0.38116 (15)0.46528 (14)0.0689 (5)
O20.27777 (18)0.21756 (13)0.39789 (12)0.0510 (4)
O30.4050 (2)0.55915 (13)0.37624 (14)0.0595 (4)
O40.31397 (19)0.57215 (12)0.24061 (13)0.0538 (4)
N10.3299 (2)0.32523 (14)0.29408 (14)0.0466 (5)
N20.2800 (2)0.40204 (14)0.26156 (14)0.0471 (5)
N30.2887 (2)0.23498 (17)0.08102 (15)0.0528 (5)
N40.4180 (2)0.20363 (17)0.09175 (15)0.0537 (5)
C10.6388 (3)0.1008 (2)0.1286 (2)0.0550 (6)
H10.60060.04970.06500.066*
C20.7676 (3)0.0703 (2)0.1377 (2)0.0626 (7)
H20.81680.00060.08090.075*
C30.8228 (3)0.1467 (2)0.2326 (2)0.0584 (6)
C40.7511 (3)0.2514 (2)0.3181 (2)0.0622 (7)
H40.78970.30180.38170.075*
C50.6217 (3)0.2810 (2)0.3087 (2)0.0574 (6)
H50.57210.35120.36700.069*
C60.5645 (3)0.20711 (19)0.21318 (18)0.0472 (5)
C70.4337 (3)0.24100 (18)0.19631 (18)0.0471 (5)
C80.2278 (3)0.33644 (19)0.15885 (17)0.0455 (5)
C90.0982 (3)0.37696 (18)0.14713 (18)0.0464 (5)
C100.0723 (3)0.3313 (2)0.0365 (2)0.0654 (7)
H100.14090.27870.03000.078*
C110.0531 (3)0.3625 (3)0.0238 (2)0.0743 (8)
H110.07040.33040.05070.089*
C120.1531 (3)0.4414 (2)0.1220 (2)0.0577 (6)
C130.1289 (3)0.4896 (2)0.2322 (2)0.0581 (6)
H130.19670.54350.29820.070*
C140.0029 (3)0.4574 (2)0.24428 (19)0.0535 (6)
H140.01430.49020.31880.064*
C150.2359 (3)0.31356 (19)0.39440 (18)0.0480 (6)
C160.2179 (2)0.20466 (18)0.50567 (17)0.0427 (5)
C170.0736 (3)0.1642 (2)0.5348 (2)0.0608 (7)
H170.01040.14970.48740.073*
C180.0238 (3)0.1452 (3)0.6362 (2)0.0693 (7)
H180.07450.11840.65840.083*
C190.1186 (3)0.1656 (2)0.7046 (2)0.0587 (7)
H190.08460.15170.77240.070*
C200.2623 (3)0.2063 (2)0.6736 (2)0.0567 (6)
H200.32600.22060.72060.068*
C210.3135 (3)0.22625 (19)0.5728 (2)0.0508 (6)
H210.41150.25390.55100.061*
C220.3416 (3)0.51822 (19)0.30030 (19)0.0465 (5)
C230.3519 (2)0.69509 (18)0.27243 (18)0.0437 (5)
C240.4158 (3)0.7261 (2)0.1798 (2)0.0564 (6)
H240.43640.66710.10170.068*
C250.4492 (3)0.8450 (2)0.2031 (2)0.0611 (7)
H250.49260.86670.14060.073*
C260.4188 (3)0.9314 (2)0.3179 (2)0.0577 (6)
H260.44221.01180.33350.069*
C270.3539 (3)0.8995 (2)0.4098 (2)0.0558 (6)
H270.33380.95850.48780.067*
C280.3182 (3)0.78065 (19)0.38806 (19)0.0498 (6)
H280.27220.75910.45050.060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0771 (5)0.0991 (6)0.1161 (6)0.0133 (4)0.0482 (5)0.0619 (5)
Cl20.0670 (5)0.0938 (5)0.0790 (5)0.0147 (4)0.0276 (4)0.0176 (4)
O10.0900 (13)0.0618 (11)0.0453 (9)0.0331 (10)0.0063 (9)0.0212 (8)
O20.0598 (10)0.0475 (9)0.0432 (8)0.0118 (7)0.0003 (7)0.0232 (7)
O30.0827 (12)0.0437 (9)0.0594 (10)0.0056 (8)0.0393 (9)0.0175 (8)
O40.0750 (11)0.0405 (8)0.0565 (9)0.0124 (8)0.0343 (8)0.0234 (7)
N10.0653 (13)0.0361 (10)0.0336 (9)0.0054 (9)0.0079 (9)0.0133 (8)
N20.0714 (13)0.0333 (9)0.0366 (10)0.0018 (9)0.0201 (9)0.0125 (8)
N30.0556 (12)0.0517 (11)0.0388 (10)0.0025 (10)0.0136 (9)0.0080 (9)
N40.0552 (13)0.0540 (11)0.0387 (11)0.0046 (9)0.0118 (9)0.0084 (9)
C10.0600 (16)0.0497 (14)0.0484 (14)0.0028 (12)0.0173 (12)0.0148 (11)
C20.0613 (17)0.0570 (15)0.0651 (16)0.0026 (13)0.0164 (13)0.0226 (13)
C30.0577 (16)0.0631 (16)0.0675 (16)0.0127 (13)0.0231 (13)0.0396 (14)
C40.0736 (19)0.0667 (17)0.0562 (15)0.0166 (14)0.0308 (14)0.0320 (14)
C50.0706 (17)0.0510 (14)0.0443 (13)0.0080 (12)0.0159 (12)0.0178 (11)
C60.0531 (14)0.0439 (12)0.0416 (12)0.0083 (11)0.0107 (11)0.0202 (10)
C70.0570 (15)0.0355 (12)0.0368 (12)0.0038 (10)0.0078 (10)0.0102 (10)
C80.0568 (15)0.0406 (12)0.0326 (11)0.0069 (11)0.0099 (10)0.0142 (10)
C90.0550 (14)0.0384 (12)0.0383 (12)0.0052 (10)0.0117 (11)0.0129 (10)
C100.0657 (18)0.0724 (17)0.0397 (13)0.0161 (14)0.0127 (12)0.0050 (12)
C110.0759 (19)0.0839 (19)0.0466 (14)0.0157 (16)0.0245 (14)0.0046 (14)
C120.0574 (15)0.0537 (14)0.0545 (15)0.0018 (12)0.0174 (12)0.0152 (12)
C130.0594 (16)0.0517 (14)0.0442 (13)0.0073 (12)0.0034 (12)0.0096 (11)
C140.0645 (16)0.0486 (13)0.0369 (12)0.0026 (12)0.0096 (11)0.0119 (11)
C150.0646 (16)0.0386 (12)0.0354 (12)0.0030 (11)0.0113 (11)0.0121 (10)
C160.0472 (13)0.0404 (11)0.0393 (11)0.0043 (10)0.0072 (10)0.0181 (9)
C170.0488 (15)0.0881 (19)0.0541 (14)0.0108 (13)0.0208 (12)0.0373 (14)
C180.0539 (16)0.092 (2)0.0645 (17)0.0150 (14)0.0118 (14)0.0444 (16)
C190.0794 (19)0.0577 (15)0.0405 (13)0.0050 (14)0.0139 (13)0.0228 (11)
C200.0656 (17)0.0561 (15)0.0514 (14)0.0029 (13)0.0261 (13)0.0183 (12)
C210.0450 (14)0.0479 (13)0.0576 (14)0.0031 (11)0.0166 (11)0.0206 (11)
C220.0588 (15)0.0386 (12)0.0387 (12)0.0010 (11)0.0153 (11)0.0125 (10)
C230.0506 (13)0.0366 (12)0.0498 (13)0.0033 (10)0.0224 (11)0.0193 (10)
C240.0758 (18)0.0497 (14)0.0427 (12)0.0018 (12)0.0194 (12)0.0168 (11)
C250.0769 (18)0.0508 (14)0.0549 (15)0.0014 (13)0.0100 (13)0.0284 (12)
C260.0650 (16)0.0408 (13)0.0638 (16)0.0005 (11)0.0116 (13)0.0235 (12)
C270.0631 (16)0.0416 (13)0.0504 (14)0.0082 (11)0.0104 (12)0.0105 (11)
C280.0522 (14)0.0502 (13)0.0465 (13)0.0044 (11)0.0079 (11)0.0230 (11)
Geometric parameters (Å, º) top
Cl1—C31.740 (3)C10—C111.372 (3)
Cl2—C121.737 (3)C10—H100.9300
O1—C151.186 (3)C11—C121.374 (3)
O2—C151.338 (3)C11—H110.9300
O2—C161.418 (2)C12—C131.371 (3)
O3—C221.192 (2)C13—C141.378 (3)
O4—C221.336 (2)C13—H130.9300
O4—C231.409 (2)C14—H140.9300
N1—C151.387 (3)C16—C171.362 (3)
N1—N21.395 (2)C16—C211.362 (3)
N1—C71.418 (3)C17—C181.377 (3)
N2—C221.392 (3)C17—H170.9300
N2—C81.419 (3)C18—C191.370 (3)
N3—C81.287 (3)C18—H180.9300
N3—N41.394 (3)C19—C201.362 (4)
N4—C71.283 (3)C19—H190.9300
C1—C21.373 (3)C20—C211.376 (3)
C1—C61.394 (3)C20—H200.9300
C1—H10.9300C21—H210.9300
C2—C31.377 (3)C23—C241.368 (3)
C2—H20.9300C23—C281.371 (3)
C3—C41.374 (4)C24—C251.373 (3)
C4—C51.376 (3)C24—H240.9300
C4—H40.9300C25—C261.366 (3)
C5—C61.389 (3)C25—H250.9300
C5—H50.9300C26—C271.368 (3)
C6—C71.463 (3)C26—H260.9300
C8—C91.459 (3)C27—C281.379 (3)
C9—C141.381 (3)C27—H270.9300
C9—C101.384 (3)C28—H280.9300
C15—O2—C16117.32 (16)C12—C13—H13120.4
C22—O4—C23119.43 (16)C14—C13—H13120.4
C15—N1—N2115.59 (18)C13—C14—C9120.9 (2)
C15—N1—C7128.13 (18)C13—C14—H14119.6
N2—N1—C7111.48 (16)C9—C14—H14119.6
C22—N2—N1115.04 (17)O1—C15—O2127.2 (2)
C22—N2—C8128.03 (17)O1—C15—N1124.1 (2)
N1—N2—C8111.39 (16)O2—C15—N1108.63 (19)
C8—N3—N4118.33 (18)C17—C16—C21122.3 (2)
C7—N4—N3118.41 (19)C17—C16—O2120.4 (2)
C2—C1—C6121.0 (2)C21—C16—O2117.1 (2)
C2—C1—H1119.5C16—C17—C18118.3 (2)
C6—C1—H1119.5C16—C17—H17120.9
C1—C2—C3118.9 (2)C18—C17—H17120.9
C1—C2—H2120.6C19—C18—C17120.3 (2)
C3—C2—H2120.6C19—C18—H18119.8
C4—C3—C2121.5 (2)C17—C18—H18119.8
C4—C3—Cl1119.7 (2)C20—C19—C18120.3 (2)
C2—C3—Cl1118.9 (2)C20—C19—H19119.9
C3—C4—C5119.3 (2)C18—C19—H19119.9
C3—C4—H4120.3C19—C20—C21120.1 (2)
C5—C4—H4120.3C19—C20—H20120.0
C4—C5—C6120.7 (2)C21—C20—H20120.0
C4—C5—H5119.7C16—C21—C20118.7 (2)
C6—C5—H5119.7C16—C21—H21120.6
C5—C6—C1118.6 (2)C20—C21—H21120.6
C5—C6—C7121.7 (2)O3—C22—O4128.0 (2)
C1—C6—C7119.6 (2)O3—C22—N2123.3 (2)
N4—C7—N1118.6 (2)O4—C22—N2108.63 (18)
N4—C7—C6120.8 (2)C24—C23—C28121.3 (2)
N1—C7—C6120.38 (19)C24—C23—O4115.73 (19)
N3—C8—N2118.6 (2)C28—C23—O4122.84 (19)
N3—C8—C9120.41 (19)C23—C24—C25119.4 (2)
N2—C8—C9120.73 (19)C23—C24—H24120.3
C14—C9—C10118.6 (2)C25—C24—H24120.3
C14—C9—C8121.80 (19)C26—C25—C24120.2 (2)
C10—C9—C8119.5 (2)C26—C25—H25119.9
C11—C10—C9120.9 (2)C24—C25—H25119.9
C11—C10—H10119.6C25—C26—C27119.9 (2)
C9—C10—H10119.6C25—C26—H26120.1
C10—C11—C12119.4 (2)C27—C26—H26120.1
C10—C11—H11120.3C26—C27—C28120.7 (2)
C12—C11—H11120.3C26—C27—H27119.6
C13—C12—C11121.0 (2)C28—C27—H27119.6
C13—C12—Cl2119.5 (2)C23—C28—C27118.5 (2)
C11—C12—Cl2119.53 (19)C23—C28—H28120.8
C12—C13—C14119.3 (2)C27—C28—H28120.8
C15—N1—N2—C2297.5 (2)C10—C11—C12—Cl2179.9 (2)
C7—N1—N2—C22104.9 (2)C11—C12—C13—C140.5 (4)
C15—N1—N2—C8106.5 (2)Cl2—C12—C13—C14179.81 (18)
C7—N1—N2—C851.1 (2)C12—C13—C14—C90.4 (4)
C8—N3—N4—C731.3 (3)C10—C9—C14—C131.5 (3)
C6—C1—C2—C30.2 (4)C8—C9—C14—C13176.6 (2)
C1—C2—C3—C40.6 (4)C16—O2—C15—O111.3 (3)
C1—C2—C3—Cl1178.93 (18)C16—O2—C15—N1166.80 (18)
C2—C3—C4—C50.2 (4)N2—N1—C15—O116.8 (3)
Cl1—C3—C4—C5179.27 (18)C7—N1—C15—O1169.9 (2)
C3—C4—C5—C60.9 (3)N2—N1—C15—O2165.12 (16)
C4—C5—C6—C11.6 (3)C7—N1—C15—O212.0 (3)
C4—C5—C6—C7175.3 (2)C15—O2—C16—C1777.1 (3)
C2—C1—C6—C51.3 (3)C15—O2—C16—C21107.4 (2)
C2—C1—C6—C7175.7 (2)C21—C16—C17—C180.3 (4)
N3—N4—C7—N18.4 (3)O2—C16—C17—C18175.6 (2)
N3—N4—C7—C6177.70 (18)C16—C17—C18—C190.7 (4)
C15—N1—C7—N4121.4 (2)C17—C18—C19—C200.8 (4)
N2—N1—C7—N432.6 (3)C18—C19—C20—C210.5 (4)
C15—N1—C7—C664.6 (3)C17—C16—C21—C200.0 (3)
N2—N1—C7—C6141.32 (19)O2—C16—C21—C20175.41 (19)
C5—C6—C7—N4151.2 (2)C19—C20—C21—C160.1 (3)
C1—C6—C7—N425.7 (3)C23—O4—C22—O35.0 (3)
C5—C6—C7—N122.6 (3)C23—O4—C22—N2173.62 (18)
C1—C6—C7—N1160.52 (19)N1—N2—C22—O316.0 (3)
N4—N3—C8—N210.0 (3)C8—N2—C22—O3167.2 (2)
N4—N3—C8—C9175.97 (18)N1—N2—C22—O4165.28 (16)
C22—N2—C8—N3121.1 (2)C8—N2—C22—O414.1 (3)
N1—N2—C8—N330.9 (3)C22—O4—C23—C24138.3 (2)
C22—N2—C8—C964.8 (3)C22—O4—C23—C2846.1 (3)
N1—N2—C8—C9143.09 (19)C28—C23—C24—C251.1 (4)
N3—C8—C9—C14155.6 (2)O4—C23—C24—C25176.8 (2)
N2—C8—C9—C1418.3 (3)C23—C24—C25—C260.0 (4)
N3—C8—C9—C1022.4 (3)C24—C25—C26—C270.4 (4)
N2—C8—C9—C10163.7 (2)C25—C26—C27—C280.2 (4)
C14—C9—C10—C111.7 (4)C24—C23—C28—C271.8 (3)
C8—C9—C10—C11176.3 (2)O4—C23—C28—C27177.1 (2)
C9—C10—C11—C120.9 (4)C26—C27—C28—C231.3 (4)
C10—C11—C12—C130.2 (4)
 

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