Download citation
Download citation
link to html
In the mol­ecule of the title compound, C19H18N2O4, the 2,8-dimethyl ester analogue of Tröger's base, the diazo­cine bridge imparts a twist such that the two aryl rings are offset with respect to one another. The dihedral angle between the two benzene rings is 96.51 (5)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028388/hk2086sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028388/hk2086Isup2.hkl
Contains datablock I

CCDC reference: 618240

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C)= 0.002 Å
  • R factor = 0.037
  • wR factor = 0.092
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT; data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN for Windows (Molecular Structure Corporation, 1998), Xtal3.6 (Hall et al., 1999) and ORTEPII (Johnson, 1976); software used to prepare material for publication: WinGX (Farrugia, 1999).

Dimethyl 6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-dicarboxylate top
Crystal data top
C19H18N2O4F(000) = 712
Mr = 338.35Dx = 1.419 Mg m3
Monoclinic, P21/cMelting point: 503.18 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 12.941 (3) ÅCell parameters from 993 reflections
b = 8.1336 (19) Åθ = 2.5–28.2°
c = 15.260 (4) ŵ = 0.10 mm1
β = 99.500 (4)°T = 150 K
V = 1584.2 (7) Å3Prism, colorless
Z = 40.36 × 0.35 × 0.27 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
3286 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.028
Graphite monochromatorθmax = 28.4°, θmin = 1.6°
ω scansh = 1717
15205 measured reflectionsk = 1010
3826 independent reflectionsl = 2019
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.21 w = 1/[σ2(Fo2) + (0.03P)2 + 0.5P]
where P = (Fo2 + 2Fc2)/3
3826 reflections(Δ/σ)max = 0.001
228 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.23 e Å3
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
O11.06881 (7)0.24832 (12)0.06321 (6)0.0349 (2)
O21.15461 (6)0.39762 (11)0.04930 (5)0.02766 (19)
O30.41205 (7)0.73125 (11)0.04450 (6)0.0345 (2)
O40.47802 (7)0.95626 (10)0.11812 (6)0.0287 (2)
N10.76172 (7)0.19775 (12)0.22794 (6)0.0224 (2)
N20.81339 (8)0.44812 (12)0.30969 (6)0.0225 (2)
C10.84020 (8)0.23048 (13)0.17413 (7)0.0203 (2)
C20.83961 (9)0.13879 (14)0.09649 (7)0.0223 (2)
H20.78710.05780.08020.027*
C30.91465 (9)0.16499 (14)0.04337 (7)0.0223 (2)
H30.91260.10410.01000.027*
C40.99365 (9)0.28132 (13)0.06819 (7)0.0210 (2)
C50.99427 (9)0.37269 (13)0.14542 (7)0.0208 (2)
H51.04820.45120.16240.025*
C60.91724 (8)0.35089 (13)0.19810 (7)0.0202 (2)
C70.91480 (9)0.46183 (14)0.27765 (7)0.0228 (2)
H7A0.97230.43090.32600.027*
H7B0.92600.57720.26080.027*
C80.73092 (9)0.53232 (14)0.25356 (7)0.0213 (2)
C90.72911 (9)0.70441 (14)0.25624 (7)0.0244 (2)
H90.78450.76200.29210.029*
C100.64784 (9)0.79109 (14)0.20743 (8)0.0244 (2)
H100.64690.90770.21030.029*
C110.56676 (9)0.70697 (14)0.15362 (7)0.0221 (2)
C120.57036 (9)0.53600 (14)0.14839 (7)0.0225 (2)
H120.51640.47920.11050.027*
C130.65170 (9)0.44716 (14)0.19769 (7)0.0214 (2)
C140.65753 (9)0.26150 (14)0.18853 (8)0.0238 (2)
H14A0.60340.20970.21840.029*
H14B0.64260.23150.12480.029*
C150.79026 (10)0.27224 (14)0.31593 (7)0.0249 (2)
H15A0.85250.21530.34870.030*
H15B0.73190.25780.34980.030*
C161.07413 (9)0.30501 (14)0.01027 (7)0.0225 (2)
C171.23573 (10)0.42884 (17)0.00326 (9)0.0310 (3)
H17A1.25900.32450.02560.046*
H17B1.29510.48320.03360.046*
H17C1.20810.50000.05350.046*
C180.47766 (9)0.79476 (14)0.09954 (7)0.0235 (2)
C190.39529 (10)1.05137 (16)0.06676 (9)0.0307 (3)
H19A0.39691.03590.00330.046*
H19B0.40541.16800.08190.046*
H19C0.32751.01480.08020.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0403 (5)0.0370 (5)0.0299 (5)0.0092 (4)0.0129 (4)0.0092 (4)
O20.0250 (4)0.0338 (5)0.0242 (4)0.0053 (3)0.0038 (3)0.0012 (3)
O30.0281 (5)0.0299 (5)0.0412 (5)0.0016 (4)0.0062 (4)0.0003 (4)
O40.0292 (4)0.0239 (4)0.0312 (4)0.0048 (3)0.0001 (3)0.0001 (3)
N10.0252 (5)0.0186 (4)0.0239 (5)0.0008 (4)0.0052 (4)0.0006 (4)
N20.0255 (5)0.0210 (5)0.0205 (4)0.0013 (4)0.0024 (4)0.0008 (4)
C10.0218 (5)0.0164 (5)0.0220 (5)0.0017 (4)0.0016 (4)0.0021 (4)
C20.0230 (5)0.0178 (5)0.0247 (5)0.0012 (4)0.0000 (4)0.0012 (4)
C30.0260 (5)0.0198 (5)0.0200 (5)0.0018 (4)0.0006 (4)0.0013 (4)
C40.0226 (5)0.0189 (5)0.0210 (5)0.0023 (4)0.0018 (4)0.0026 (4)
C50.0208 (5)0.0176 (5)0.0223 (5)0.0001 (4)0.0013 (4)0.0012 (4)
C60.0221 (5)0.0174 (5)0.0195 (5)0.0019 (4)0.0011 (4)0.0002 (4)
C70.0232 (5)0.0223 (5)0.0218 (5)0.0000 (4)0.0007 (4)0.0036 (4)
C80.0233 (5)0.0217 (5)0.0192 (5)0.0006 (4)0.0048 (4)0.0007 (4)
C90.0263 (6)0.0220 (5)0.0236 (5)0.0024 (4)0.0008 (4)0.0039 (4)
C100.0281 (6)0.0188 (5)0.0262 (6)0.0009 (4)0.0042 (4)0.0017 (4)
C110.0217 (5)0.0224 (5)0.0228 (5)0.0002 (4)0.0053 (4)0.0002 (4)
C120.0201 (5)0.0229 (5)0.0249 (5)0.0038 (4)0.0045 (4)0.0023 (4)
C130.0228 (5)0.0195 (5)0.0230 (5)0.0019 (4)0.0068 (4)0.0011 (4)
C140.0226 (5)0.0199 (5)0.0292 (6)0.0029 (4)0.0049 (4)0.0018 (4)
C150.0309 (6)0.0220 (5)0.0222 (5)0.0017 (5)0.0056 (4)0.0020 (4)
C160.0249 (5)0.0181 (5)0.0239 (5)0.0016 (4)0.0027 (4)0.0028 (4)
C170.0249 (6)0.0350 (7)0.0342 (6)0.0016 (5)0.0082 (5)0.0067 (5)
C180.0228 (5)0.0238 (5)0.0250 (5)0.0011 (4)0.0072 (4)0.0013 (4)
C190.0298 (6)0.0280 (6)0.0340 (7)0.0068 (5)0.0040 (5)0.0058 (5)
Geometric parameters (Å, º) top
O1—C161.2039 (14)C7—H7A0.9900
O2—C161.3424 (14)C7—H7B0.9900
O2—C171.4449 (14)C8—C91.4007 (16)
O3—C181.2074 (14)C8—C131.4032 (15)
O4—C181.3436 (15)C9—C101.3782 (16)
O4—C191.4430 (14)C9—H90.9500
N1—C11.4325 (14)C10—C111.3997 (16)
N1—C151.4638 (15)C10—H100.9500
N1—C141.4768 (15)C11—C121.3941 (16)
N2—C81.4283 (14)C11—C181.4853 (16)
N2—C151.4678 (15)C12—C131.3909 (16)
N2—C71.4785 (15)C12—H120.9500
C1—C21.3989 (16)C13—C141.5196 (16)
C1—C61.4023 (15)C14—H14A0.9900
C2—C31.3803 (16)C14—H14B0.9900
C2—H20.9500C15—H15A0.9900
C3—C41.3985 (16)C15—H15B0.9900
C3—H30.9500C17—H17A0.9800
C4—C51.3922 (16)C17—H17B0.9800
C4—C161.4855 (16)C17—H17C0.9800
C5—C61.3913 (16)C19—H19A0.9800
C5—H50.9500C19—H19B0.9800
C6—C71.5171 (15)C19—H19C0.9800
C16—O2—C17115.71 (9)C11—C10—H10120.1
C18—O4—C19115.66 (9)C12—C11—C10119.49 (11)
C1—N1—C15110.70 (9)C12—C11—C18118.55 (10)
C1—N1—C14112.79 (9)C10—C11—C18121.94 (10)
C15—N1—C14107.66 (9)C13—C12—C11121.11 (10)
C8—N2—C15111.47 (9)C13—C12—H12119.4
C8—N2—C7112.44 (9)C11—C12—H12119.4
C15—N2—C7107.25 (9)C12—C13—C8118.95 (10)
C2—C1—C6119.84 (10)C12—C13—C14120.74 (10)
C2—C1—N1118.76 (10)C8—C13—C14120.26 (10)
C6—C1—N1121.40 (10)N1—C14—C13111.55 (9)
C3—C2—C1120.59 (10)N1—C14—H14A109.3
C3—C2—H2119.7C13—C14—H14A109.3
C1—C2—H2119.7N1—C14—H14B109.3
C2—C3—C4119.94 (10)C13—C14—H14B109.3
C2—C3—H3120.0H14A—C14—H14B108.0
C4—C3—H3120.0N1—C15—N2111.54 (9)
C5—C4—C3119.48 (10)N1—C15—H15A109.3
C5—C4—C16121.85 (10)N2—C15—H15A109.3
C3—C4—C16118.66 (10)N1—C15—H15B109.3
C6—C5—C4121.10 (10)N2—C15—H15B109.3
C6—C5—H5119.5H15A—C15—H15B108.0
C4—C5—H5119.5O1—C16—O2123.30 (11)
C5—C6—C1118.99 (10)O1—C16—C4124.51 (11)
C5—C6—C7119.87 (10)O2—C16—C4112.19 (10)
C1—C6—C7121.09 (10)O2—C17—H17A109.5
N2—C7—C6110.89 (9)O2—C17—H17B109.5
N2—C7—H7A109.5H17A—C17—H17B109.5
C6—C7—H7A109.5O2—C17—H17C109.5
N2—C7—H7B109.5H17A—C17—H17C109.5
C6—C7—H7B109.5H17B—C17—H17C109.5
H7A—C7—H7B108.0O3—C18—O4122.86 (11)
C9—C8—C13119.80 (10)O3—C18—C11124.97 (11)
C9—C8—N2118.43 (10)O4—C18—C11112.17 (10)
C13—C8—N2121.76 (10)O4—C19—H19A109.5
C10—C9—C8120.69 (11)O4—C19—H19B109.5
C10—C9—H9119.7H19A—C19—H19B109.5
C8—C9—H9119.7O4—C19—H19C109.5
C9—C10—C11119.89 (11)H19A—C19—H19C109.5
C9—C10—H10120.1H19B—C19—H19C109.5
C15—N1—C1—C2165.18 (10)C9—C10—C11—C18179.79 (10)
C14—N1—C1—C274.12 (13)C10—C11—C12—C131.83 (17)
C15—N1—C1—C614.38 (14)C18—C11—C12—C13179.80 (10)
C14—N1—C1—C6106.33 (12)C11—C12—C13—C80.13 (16)
C6—C1—C2—C30.40 (16)C11—C12—C13—C14177.30 (10)
N1—C1—C2—C3179.16 (10)C9—C8—C13—C122.43 (16)
C1—C2—C3—C41.55 (17)N2—C8—C13—C12176.41 (10)
C2—C3—C4—C51.56 (16)C9—C8—C13—C14175.01 (10)
C2—C3—C4—C16179.15 (10)N2—C8—C13—C146.15 (16)
C3—C4—C5—C60.38 (16)C1—N1—C14—C1374.89 (12)
C16—C4—C5—C6178.89 (10)C15—N1—C14—C1347.53 (12)
C4—C5—C6—C12.30 (16)C12—C13—C14—N1165.36 (10)
C4—C5—C6—C7174.97 (10)C8—C13—C14—N112.03 (14)
C2—C1—C6—C52.30 (16)C1—N1—C15—N253.33 (12)
N1—C1—C6—C5177.25 (10)C14—N1—C15—N270.37 (11)
C2—C1—C6—C7174.94 (10)C8—N2—C15—N151.70 (12)
N1—C1—C6—C75.52 (16)C7—N2—C15—N171.78 (11)
C8—N2—C7—C675.33 (11)C17—O2—C16—O11.01 (16)
C15—N2—C7—C647.55 (11)C17—O2—C16—C4179.05 (9)
C5—C6—C7—N2165.08 (9)C5—C4—C16—O1168.32 (11)
C1—C6—C7—N212.13 (14)C3—C4—C16—O110.95 (17)
C15—N2—C8—C9165.76 (10)C5—C4—C16—O211.74 (15)
C7—N2—C8—C973.76 (13)C3—C4—C16—O2168.98 (10)
C15—N2—C8—C1313.09 (14)C19—O4—C18—O31.00 (16)
C7—N2—C8—C13107.39 (11)C19—O4—C18—C11178.54 (9)
C13—C8—C9—C102.80 (17)C12—C11—C18—O37.19 (18)
N2—C8—C9—C10176.07 (10)C10—C11—C18—O3171.14 (11)
C8—C9—C10—C110.83 (17)C12—C11—C18—O4173.29 (10)
C9—C10—C11—C121.48 (17)C10—C11—C18—O48.39 (15)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds