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In the mol­ecule of the title compound, C15H10Br4N2, the 2,4,8,10-tetra­bromo analogue of Tröger's base, the two aryl rings are offset with respect to one another by virtue of the diazo­cine bridge. The dihedral angle of 108.44 (4)° between the two benzene rings is the largest yet measured for a dibenzo system.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031734/hk2104sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031734/hk2104Isup2.hkl
Contains datablock I

CCDC reference: 621366

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.024
  • wR factor = 0.053
  • Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT431_ALERT_2_C Short Inter HL..A Contact Br3 .. Br4 .. 3.55 Ang.
Alert level G ABSTM02_ALERT_3_G The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.042 0.519 Tmin and Tmax expected: 0.033 0.517 RR = 1.285 Please check that your absorption correction is appropriate. 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 28.30 From the CIF: _reflns_number_total 3662 Count of symmetry unique reflns 1986 Completeness (_total/calc) 184.39% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1676 Fraction of Friedel pairs measured 0.844 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1995); cell refinement: SAINT; data reduction: SAINT and XPREP (Bruker, 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) ORTEPII (Johnson, 1976); software used to prepare material for publication: WinGX (Farrugia, 1999).

2,4,8,10-tetrabromo-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine top
Crystal data top
C15H10Br4N2Dx = 2.323 Mg m3
Mr = 537.89Melting point: 498.33K K
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 1012 reflections
a = 8.040 (3) Åθ = 3.0–28.3°
b = 12.475 (4) ŵ = 10.46 mm1
c = 15.331 (5) ÅT = 150 K
V = 1537.7 (9) Å3Plate, colorless
Z = 40.48 × 0.30 × 0.06 mm
F(000) = 1016
Data collection top
Bruker SMART 1000 CCD
diffractometer
3662 independent reflections
Radiation source: sealed tube3419 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
ω scansθmax = 28.3°, θmin = 1.6°
Absorption correction: gaussian
[(Coppens et al., 1965) using XPREP (Bruker, 1995)]
h = 1010
Tmin = 0.042, Tmax = 0.519k = 1616
13979 measured reflectionsl = 1920
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)] = 0.024H-atom parameters constrained
wR(F2) = 0.053 w = 1/[σ2(Fo2) + (0.02P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.002
3662 reflectionsΔρmax = 0.60 e Å3
191 parametersΔρmin = 0.66 e Å3
1 restraintAbsolute structure: Flack (1983), 1686 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.004 (10)
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
Br10.48729 (5)0.01522 (3)0.26532 (2)0.02456 (9)
Br20.30256 (5)0.19191 (3)0.59144 (2)0.02592 (9)
Br30.07020 (5)0.45333 (3)0.56818 (2)0.02194 (9)
Br40.26941 (4)0.41528 (4)0.24542 (2)0.02277 (9)
N10.3313 (4)0.3179 (3)0.47455 (17)0.0175 (6)
N20.4448 (4)0.1997 (3)0.36359 (18)0.0177 (6)
C10.3971 (4)0.1088 (3)0.4143 (2)0.0186 (7)
C20.4128 (5)0.0048 (3)0.3821 (2)0.0197 (8)
C30.3808 (5)0.0860 (3)0.4319 (2)0.0211 (8)
H30.39150.15590.40780.025*
C40.3326 (5)0.0711 (3)0.5182 (2)0.0216 (8)
C50.3095 (4)0.0304 (3)0.5521 (2)0.0202 (8)
H50.27270.03860.61060.024*
C60.3400 (4)0.1211 (3)0.50080 (19)0.0184 (7)
C70.3149 (5)0.2320 (3)0.5397 (2)0.0192 (7)
H7A0.20300.23590.56640.023*
H7B0.39790.24350.58650.023*
C80.1862 (4)0.3339 (3)0.4224 (2)0.0178 (7)
C90.0536 (5)0.3930 (3)0.45464 (19)0.0174 (7)
C100.0862 (4)0.4155 (3)0.4050 (2)0.0182 (7)
H100.17720.45440.42860.022*
C110.0880 (4)0.3790 (3)0.31942 (19)0.0190 (8)
C120.0398 (5)0.3196 (3)0.28527 (19)0.0182 (8)
H120.03310.29410.22700.022*
C130.1794 (5)0.2964 (3)0.3356 (2)0.0169 (7)
C140.3210 (4)0.2325 (3)0.2975 (2)0.0190 (8)
H14A0.27560.16760.26890.023*
H14B0.37710.27590.25220.023*
C150.4756 (5)0.2929 (3)0.4195 (2)0.0204 (8)
H15A0.50200.35570.38250.024*
H15B0.57320.27840.45710.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02964 (19)0.0267 (2)0.01731 (15)0.00924 (18)0.00462 (15)0.00175 (15)
Br20.0328 (2)0.0220 (2)0.02292 (16)0.00012 (19)0.00032 (15)0.00505 (15)
Br30.02755 (18)0.02223 (19)0.01603 (13)0.00005 (17)0.00181 (13)0.00601 (14)
Br40.02162 (16)0.0277 (2)0.01895 (16)0.00446 (17)0.00086 (13)0.00370 (14)
N10.0176 (15)0.0167 (16)0.0181 (13)0.0017 (14)0.0002 (11)0.0015 (11)
N20.0166 (14)0.0207 (18)0.0157 (12)0.0004 (14)0.0016 (11)0.0005 (11)
C10.0156 (16)0.023 (2)0.0171 (14)0.0006 (16)0.0011 (12)0.0016 (14)
C20.0199 (18)0.025 (2)0.0143 (14)0.0048 (16)0.0004 (13)0.0007 (14)
C30.0241 (18)0.020 (2)0.0195 (15)0.0036 (18)0.0006 (14)0.0009 (14)
C40.0227 (19)0.023 (2)0.0193 (16)0.0036 (18)0.0017 (14)0.0046 (14)
C50.0199 (17)0.027 (2)0.0136 (15)0.0035 (17)0.0015 (12)0.0009 (13)
C60.0147 (17)0.021 (2)0.0191 (15)0.0008 (17)0.0026 (12)0.0029 (14)
C70.0233 (18)0.019 (2)0.0151 (14)0.0014 (17)0.0015 (13)0.0021 (14)
C80.0203 (18)0.0154 (19)0.0177 (15)0.0039 (16)0.0018 (13)0.0010 (13)
C90.0225 (17)0.017 (2)0.0131 (13)0.0036 (17)0.0023 (12)0.0013 (13)
C100.0188 (17)0.018 (2)0.0177 (14)0.0003 (16)0.0035 (12)0.0011 (13)
C110.0213 (19)0.018 (2)0.0179 (15)0.0029 (17)0.0029 (13)0.0032 (13)
C120.0246 (18)0.019 (2)0.0106 (14)0.0000 (17)0.0009 (12)0.0014 (12)
C130.0210 (17)0.0124 (18)0.0173 (14)0.0031 (16)0.0036 (12)0.0009 (13)
C140.0196 (18)0.024 (2)0.0139 (13)0.0001 (17)0.0010 (13)0.0001 (14)
C150.0191 (19)0.020 (2)0.0216 (15)0.0046 (17)0.0002 (13)0.0002 (15)
Geometric parameters (Å, º) top
Br1—C21.905 (3)C5—H50.9500
Br2—C41.896 (4)C6—C71.521 (5)
Br3—C91.901 (3)C7—H7A0.9900
Br4—C111.903 (3)C7—H7B0.9900
N1—C81.428 (4)C8—C91.387 (5)
N1—C151.469 (5)C8—C131.411 (5)
N1—C71.470 (5)C9—C101.386 (5)
N2—C11.429 (5)C10—C111.390 (4)
N2—C151.465 (5)C10—H100.9500
N2—C141.478 (5)C11—C121.371 (5)
C1—C21.394 (5)C12—C131.393 (5)
C1—C61.411 (4)C12—H120.9500
C2—C31.390 (5)C13—C141.509 (5)
C3—C41.391 (5)C14—H14A0.9900
C3—H30.9500C14—H14B0.9900
C4—C51.381 (5)C15—H15A0.9900
C5—C61.400 (5)C15—H15B0.9900
C8—N1—C15110.7 (3)C9—C8—C13118.8 (3)
C8—N1—C7114.2 (3)C9—C8—N1120.2 (3)
C15—N1—C7107.9 (3)C13—C8—N1120.8 (3)
C1—N2—C15110.9 (3)C10—C9—C8122.4 (3)
C1—N2—C14114.3 (3)C10—C9—Br3118.6 (3)
C15—N2—C14107.2 (3)C8—C9—Br3118.9 (3)
C2—C1—C6117.6 (3)C9—C10—C11117.4 (3)
C2—C1—N2121.5 (3)C9—C10—H10121.3
C6—C1—N2120.8 (4)C11—C10—H10121.3
C3—C2—C1123.2 (3)C12—C11—C10122.0 (3)
C3—C2—Br1117.9 (3)C12—C11—Br4118.4 (2)
C1—C2—Br1118.9 (3)C10—C11—Br4119.5 (3)
C2—C3—C4117.6 (4)C11—C12—C13120.3 (3)
C2—C3—H3121.2C11—C12—H12119.9
C4—C3—H3121.2C13—C12—H12119.9
C5—C4—C3121.3 (4)C12—C13—C8119.0 (3)
C5—C4—Br2119.2 (2)C12—C13—C14120.2 (3)
C3—C4—Br2119.5 (3)C8—C13—C14120.8 (3)
C4—C5—C6120.4 (3)N2—C14—C13112.8 (3)
C4—C5—H5119.8N2—C14—H14A109.0
C6—C5—H5119.8C13—C14—H14A109.0
C5—C6—C1119.8 (4)N2—C14—H14B109.0
C5—C6—C7119.5 (3)C13—C14—H14B109.0
C1—C6—C7120.7 (3)H14A—C14—H14B107.8
N1—C7—C6112.6 (3)N2—C15—N1111.8 (3)
N1—C7—H7A109.1N2—C15—H15A109.3
C6—C7—H7A109.1N1—C15—H15A109.3
N1—C7—H7B109.1N2—C15—H15B109.3
C6—C7—H7B109.1N1—C15—H15B109.3
H7A—C7—H7B107.8H15A—C15—H15B107.9
C15—N2—C1—C2159.0 (3)C15—N1—C8—C1318.2 (5)
C14—N2—C1—C279.6 (4)C7—N1—C8—C13103.7 (4)
C15—N2—C1—C617.7 (4)C13—C8—C9—C100.8 (6)
C14—N2—C1—C6103.6 (4)N1—C8—C9—C10176.6 (3)
C6—C1—C2—C32.4 (6)C13—C8—C9—Br3175.0 (3)
N2—C1—C2—C3174.5 (3)N1—C8—C9—Br30.8 (5)
C6—C1—C2—Br1179.4 (3)C8—C9—C10—C111.8 (6)
N2—C1—C2—Br13.8 (5)Br3—C9—C10—C11174.0 (3)
C1—C2—C3—C40.7 (6)C9—C10—C11—C122.3 (6)
Br1—C2—C3—C4177.6 (3)C9—C10—C11—Br4175.8 (3)
C2—C3—C4—C53.0 (6)C10—C11—C12—C131.8 (6)
C2—C3—C4—Br2175.6 (3)Br4—C11—C12—C13176.3 (3)
C3—C4—C5—C62.2 (6)C11—C12—C13—C80.8 (6)
Br2—C4—C5—C6176.4 (3)C11—C12—C13—C14179.1 (3)
C4—C5—C6—C11.0 (6)C9—C8—C13—C120.2 (5)
C4—C5—C6—C7179.6 (3)N1—C8—C13—C12176.0 (3)
C2—C1—C6—C53.2 (5)C9—C8—C13—C14179.6 (3)
N2—C1—C6—C5173.7 (3)N1—C8—C13—C143.8 (5)
C2—C1—C6—C7178.2 (3)C1—N2—C14—C1379.4 (4)
N2—C1—C6—C74.9 (5)C15—N2—C14—C1343.9 (4)
C8—N1—C7—C680.4 (4)C12—C13—C14—N2170.2 (3)
C15—N1—C7—C643.1 (4)C8—C13—C14—N210.0 (5)
C5—C6—C7—N1172.6 (3)C1—N2—C15—N155.6 (4)
C1—C6—C7—N18.8 (5)C14—N2—C15—N169.8 (4)
C15—N1—C8—C9157.5 (4)C8—N1—C15—N256.1 (4)
C7—N1—C8—C980.5 (4)C7—N1—C15—N269.5 (3)
 

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