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The title compound, C18H18N4O2, was prepared from prop­yl chloro­formate and 3,6-diphen­yl-1,2-dihydro-1,2,4,5-tetra­zine. The central six-membered ring has a boat conformation. In the crystal structure, mol­ecules are linked via N—H...N [N...N = 3.015 (4) Å] and C—H...O [C...O = 3.265 (6) Å] hydrogen bonds to form extended chains along [100].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019653/lh6426sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019653/lh6426Isup2.hkl
Contains datablock I

CCDC reference: 255696

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.036
  • wR factor = 0.105
  • Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.23 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.55 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C18 H18 N4 O2
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.17 From the CIF: _reflns_number_total 1584 Count of symmetry unique reflns 1584 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 2 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 for Windows (Version 1.05; Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Propyl 3,6-diphenyl-1,4-dihydro-1,2,4,5-tetrazine-1-carboxylate top
Crystal data top
C18H18N4O2Dx = 1.256 Mg m3
Mr = 322.36Melting point = 414–415 K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 25 reflections
a = 10.212 (3) Åθ = 10.7–12.5°
b = 10.051 (2) ŵ = 0.09 mm1
c = 16.611 (3) ÅT = 298 K
V = 1705.0 (7) Å3Prism, yellow
Z = 40.40 × 0.30 × 0.20 mm
F(000) = 680
Data collection top
Enraf–Nonius CAD-4
diffractometer
997 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 25.2°, θmin = 2.4°
ω/2θ scansh = 012
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 012
Tmin = 0.967, Tmax = 0.983l = 191
1699 measured reflections3 standard reflections every 60 min
1584 independent reflections intensity decay: 0.3%
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)] = 0.036H-atom parameters constrained
wR(F2) = 0.106 w = 1/[σ2(Fo2) + (0.0614P)2 + 0.0145P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
1584 reflectionsΔρmax = 0.16 e Å3
219 parametersΔρmin = 0.20 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.012 (2)
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
O10.7283 (3)0.9489 (3)0.84478 (18)0.0657 (8)
O20.5803 (3)0.8911 (2)0.93879 (19)0.0609 (7)
N10.5679 (3)1.0914 (3)0.88319 (18)0.0488 (7)
N20.6018 (3)1.1779 (3)0.81813 (17)0.0437 (7)
N40.3808 (3)1.2267 (3)0.83220 (18)0.0545 (9)
H30.30751.22700.80660.065*
N50.3855 (3)1.2151 (3)0.91595 (18)0.0523 (8)
C10.3992 (4)1.1114 (4)1.0793 (2)0.0601 (11)
H10.31451.11041.05880.072*
C20.4188 (4)1.0979 (5)1.1606 (3)0.0714 (13)
H20.34751.08811.19490.086*
C80.5440 (5)1.0988 (5)1.1914 (3)0.0704 (12)
H3A0.55781.08921.24640.084*
C40.6478 (4)1.1140 (4)1.1402 (3)0.0702 (12)
H40.73241.11561.16090.084*
C50.6294 (4)1.1270 (4)1.0589 (2)0.0574 (11)
H50.70111.13601.02490.069*
C70.5038 (4)1.1266 (3)1.0275 (2)0.0482 (9)
C60.4801 (3)1.1436 (4)0.9411 (2)0.0444 (8)
C30.4989 (3)1.2378 (4)0.7922 (2)0.0457 (8)
C90.5080 (3)1.3221 (4)0.7203 (2)0.0463 (8)
C100.5954 (5)1.2894 (5)0.6597 (3)0.0700 (12)
H100.64501.21200.66310.084*
C110.6078 (5)1.3727 (6)0.5943 (3)0.0934 (17)
H110.66621.35020.55360.112*
C120.5372 (5)1.4874 (6)0.5875 (3)0.0761 (14)
H120.54791.54330.54330.091*
C130.4516 (4)1.5175 (5)0.6461 (3)0.0685 (13)
H130.40171.59450.64170.082*
C140.4360 (4)1.4382 (4)0.7119 (3)0.0615 (11)
H140.37641.46220.75170.074*
C150.6351 (3)0.9741 (3)0.8865 (2)0.0476 (9)
C160.6410 (4)0.7604 (4)0.9436 (3)0.0641 (11)
H16A0.62350.72240.99620.077*
H16B0.73510.77020.93830.077*
C170.5933 (5)0.6675 (4)0.8808 (3)0.0869 (15)
H17A0.60650.70660.82800.104*
H17B0.50020.65230.88800.104*
C180.6654 (7)0.5372 (5)0.8859 (4)0.113 (2)
H18A0.65800.50210.93950.170*
H18B0.75610.55100.87320.170*
H18C0.62810.47520.84840.170*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0576 (16)0.0699 (16)0.0697 (18)0.0170 (13)0.0202 (15)0.0012 (14)
O20.0640 (16)0.0445 (16)0.0744 (16)0.0031 (12)0.0166 (15)0.0030 (15)
N10.0453 (15)0.0531 (18)0.0481 (17)0.0051 (13)0.0101 (15)0.0010 (16)
N20.0373 (15)0.0487 (16)0.0452 (16)0.0002 (13)0.0069 (14)0.0000 (14)
N40.0299 (16)0.083 (2)0.0505 (18)0.0020 (15)0.0033 (14)0.0038 (16)
N50.0401 (17)0.066 (2)0.0503 (19)0.0044 (16)0.0098 (14)0.0025 (14)
C10.044 (2)0.083 (3)0.053 (3)0.000 (2)0.0090 (19)0.007 (2)
C20.061 (3)0.096 (4)0.058 (3)0.001 (2)0.016 (2)0.013 (2)
C80.075 (3)0.085 (3)0.051 (2)0.003 (2)0.002 (2)0.006 (2)
C40.059 (2)0.087 (3)0.065 (3)0.010 (2)0.008 (2)0.002 (2)
C50.045 (2)0.073 (3)0.055 (2)0.0005 (19)0.0058 (19)0.006 (2)
C70.0463 (19)0.045 (2)0.053 (2)0.0015 (17)0.0079 (17)0.0015 (18)
C60.0356 (16)0.0477 (19)0.050 (2)0.0015 (16)0.0116 (18)0.0035 (17)
C30.0370 (19)0.052 (2)0.0479 (19)0.0029 (15)0.0020 (16)0.0108 (18)
C90.0358 (18)0.058 (2)0.0448 (19)0.0032 (17)0.0031 (17)0.0046 (17)
C100.079 (3)0.074 (3)0.056 (3)0.013 (2)0.021 (2)0.001 (2)
C110.108 (4)0.104 (4)0.068 (3)0.015 (3)0.035 (3)0.011 (3)
C120.067 (3)0.093 (4)0.068 (3)0.016 (3)0.002 (3)0.021 (3)
C130.056 (2)0.073 (3)0.076 (3)0.009 (2)0.003 (2)0.020 (3)
C140.051 (2)0.075 (3)0.059 (3)0.008 (2)0.0044 (19)0.004 (2)
C150.0442 (19)0.051 (2)0.047 (2)0.0030 (16)0.0015 (19)0.0073 (18)
C160.069 (3)0.055 (3)0.068 (2)0.002 (2)0.006 (2)0.001 (2)
C170.092 (3)0.063 (3)0.106 (4)0.007 (2)0.033 (3)0.011 (3)
C180.142 (5)0.067 (3)0.131 (5)0.022 (3)0.031 (4)0.026 (3)
Geometric parameters (Å, º) top
O1—C151.204 (4)C7—C61.466 (5)
O2—C151.328 (5)C3—C91.467 (5)
O2—C161.455 (5)C9—C101.385 (5)
N1—C151.366 (4)C9—C141.386 (6)
N1—C61.415 (4)C10—C111.377 (6)
N1—N21.429 (4)C10—H100.9300
N2—C31.285 (4)C11—C121.365 (7)
N4—C31.381 (5)C11—H110.9300
N4—N51.397 (4)C12—C131.343 (6)
N4—H30.8600C12—H120.9300
N5—C61.275 (5)C13—C141.362 (6)
C1—C21.372 (6)C13—H130.9300
C1—C71.379 (5)C14—H140.9300
C1—H10.9300C16—C171.482 (6)
C2—C81.378 (6)C16—H16A0.9700
C2—H20.9300C16—H16B0.9700
C8—C41.367 (6)C17—C181.505 (6)
C8—H3A0.9300C17—H17A0.9700
C4—C51.369 (6)C17—H17B0.9700
C4—H40.9300C18—H18A0.9600
C5—C71.384 (5)C18—H18B0.9600
C5—H50.9300C18—H18C0.9600
C15—O2—C16115.1 (3)C11—C10—C9119.2 (4)
C15—N1—C6127.6 (3)C11—C10—H10120.4
C15—N1—N2115.7 (3)C9—C10—H10120.4
C6—N1—N2116.2 (3)C12—C11—C10122.1 (5)
C3—N2—N1109.9 (3)C12—C11—H11119.0
C3—N4—N5117.1 (3)C10—C11—H11119.0
C3—N4—H3121.5C13—C12—C11118.2 (4)
N5—N4—H3121.5C13—C12—H12120.9
C6—N5—N4113.5 (3)C11—C12—H12120.9
C2—C1—C7120.8 (4)C12—C13—C14121.8 (4)
C2—C1—H1119.6C12—C13—H13119.1
C7—C1—H1119.6C14—C13—H13119.1
C1—C2—C8120.0 (4)C13—C14—C9120.7 (4)
C1—C2—H2120.0C13—C14—H14119.6
C8—C2—H2120.0C9—C14—H14119.6
C4—C8—C2119.3 (4)O1—C15—O2125.3 (3)
C4—C8—H3A120.4O1—C15—N1123.8 (4)
C2—C8—H3A120.4O2—C15—N1110.9 (3)
C8—C4—C5121.1 (4)O2—C16—C17112.9 (4)
C8—C4—H4119.4O2—C16—H16A109.0
C5—C4—H4119.4C17—C16—H16A109.0
C4—C5—C7119.9 (4)O2—C16—H16B109.0
C4—C5—H5120.1C17—C16—H16B109.0
C7—C5—H5120.1H16A—C16—H16B107.8
C1—C7—C5118.9 (4)C16—C17—C18110.3 (4)
C1—C7—C6119.7 (3)C16—C17—H17A109.6
C5—C7—C6121.4 (3)C18—C17—H17A109.6
N5—C6—N1117.8 (3)C16—C17—H17B109.6
N5—C6—C7120.8 (3)C18—C17—H17B109.6
N1—C6—C7121.2 (3)H17A—C17—H17B108.1
N2—C3—N4121.0 (3)C17—C18—H18A109.5
N2—C3—C9119.4 (3)C17—C18—H18B109.5
N4—C3—C9119.6 (3)H18A—C18—H18B109.5
C10—C9—C14117.9 (4)C17—C18—H18C109.5
C10—C9—C3119.7 (3)H18A—C18—H18C109.5
C14—C9—C3122.3 (3)H18B—C18—H18C109.5
C15—N1—N2—C3143.6 (3)N5—N4—C3—N233.6 (5)
C6—N1—N2—C343.3 (4)N5—N4—C3—C9144.7 (3)
C3—N4—N5—C638.3 (5)N2—C3—C9—C1032.5 (5)
C7—C1—C2—C80.3 (7)N4—C3—C9—C10149.1 (4)
C1—C2—C8—C40.4 (7)N2—C3—C9—C14144.4 (4)
C2—C8—C4—C50.7 (7)N4—C3—C9—C1433.9 (5)
C8—C4—C5—C70.9 (7)C14—C9—C10—C110.3 (6)
C2—C1—C7—C50.4 (6)C3—C9—C10—C11176.8 (4)
C2—C1—C7—C6178.7 (4)C9—C10—C11—C120.4 (8)
C4—C5—C7—C10.7 (6)C10—C11—C12—C131.1 (8)
C4—C5—C7—C6178.4 (4)C11—C12—C13—C141.2 (7)
N4—N5—C6—N12.4 (5)C12—C13—C14—C90.5 (7)
N4—N5—C6—C7176.8 (3)C10—C9—C14—C130.3 (6)
C15—N1—C6—N5148.4 (3)C3—C9—C14—C13176.7 (4)
N2—N1—C6—N539.4 (4)C16—O2—C15—O10.2 (5)
C15—N1—C6—C737.2 (5)C16—O2—C15—N1177.0 (3)
N2—N1—C6—C7135.0 (3)C6—N1—C15—O1163.2 (4)
C1—C7—C6—N539.7 (6)N2—N1—C15—O19.1 (5)
C5—C7—C6—N5139.4 (4)C6—N1—C15—O219.6 (5)
C1—C7—C6—N1146.0 (3)N2—N1—C15—O2168.1 (3)
C5—C7—C6—N134.8 (5)C15—O2—C16—C1783.7 (5)
N1—N2—C3—N47.5 (4)O2—C16—C17—C18176.7 (5)
N1—N2—C3—C9174.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H3···N2i0.862.323.015 (4)139
C14—H14···O1i0.932.343.265 (6)172
Symmetry code: (i) x1/2, y+5/2, z.
 

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