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organic compounds
5,11-Dimethyldibenzo[b,f][1,5]diazocine-6,12(5H,11H)-dione
aDepartment of Chemistry and Biomolecular Sciences, Building F7B, Macquarie University, NSW 2109, Australia, and bCrystal Structure Analysis Facility, School of Chemistry, F11, University of Sydney, NSW 2006, Australia
*Correspondence e-mail: andrew.try@mq.edu.au
In the molecule of the title compound, C16H14N2O2, an N,N′-dimethyldianthranilide, the two methyl groups are disordered over two positions; site occupation factors were kept fixed as 0.75:0.25 and 0.65:0.35. The dihedral angle between the two benzene rings is 75.57 (3)°.
Related literature
For related literature, see: Nadkarni & Hosangadi (1988). For related structures, see: Ebert et al. (1998
); Nonnenmacher et al. (2000
); Gordon-Wylie et al. (2004
); Olszewska et al. (2004
).
Experimental
Crystal data
|
Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 2003
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: X-SEED (Barbour, 2001
) and SHELXTL (Sheldrick, 2008
); software used to prepare material for publication: modiCIFer (Guzei, 2005
).
Supporting information
10.1107/S1600536808001281/hk2415sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808001281/hk2415Isup2.hkl
The title compound was prepared according to the literature procedure (Nadkarni & Hosangadi, 1988) in 89% yield. Single crystals of (I) were produced from slow evaporation of a dichloromethane solution.
When the
was solved, the two methyl groups were found to be disordered. They were each modelled with disorder over two positions with a common carbon atom. One was assigned a 75:25 split occupancy, the other 65:35. A rotating was used for each methyl position giving staggered orientations for each. H atoms were positioned geometrically, with C—H = 0.95 and 0.98 Å for aromatic and methyl H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).Data collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and SHELXTL (Bruker, 2003); software used to prepare material for publication: modiCIFer (Version Dec-16-2005; Guzei, 2005).C16H14N2O2 | F(000) = 560 |
Mr = 266.29 | Dx = 1.314 Mg m−3 |
Monoclinic, P21/c | Melting point: 484 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 11.2715 (10) Å | Cell parameters from 5797 reflections |
b = 7.9113 (7) Å | θ = 2.7–28.3° |
c = 15.4100 (14) Å | µ = 0.09 mm−1 |
β = 101.611 (1)° | T = 150 K |
V = 1346.0 (2) Å3 | Prism, colourless |
Z = 4 | 0.55 × 0.42 × 0.24 mm |
Bruker 1000 CCD area-detector diffractometer | 3175 independent reflections |
Radiation source: fine-focus sealed tube | 2686 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω scans | θmax = 28.3°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.901, Tmax = 0.979 | k = −10→10 |
12897 measured reflections | l = −20→20 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0528P)2 + 0.3606P] where P = (Fo2 + 2Fc2)/3 |
3175 reflections | (Δ/σ)max < 0.001 |
185 parameters | Δρmax = 0.23 e Å−3 |
1 restraint | Δρmin = −0.23 e Å−3 |
C16H14N2O2 | V = 1346.0 (2) Å3 |
Mr = 266.29 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 11.2715 (10) Å | µ = 0.09 mm−1 |
b = 7.9113 (7) Å | T = 150 K |
c = 15.4100 (14) Å | 0.55 × 0.42 × 0.24 mm |
β = 101.611 (1)° |
Bruker 1000 CCD area-detector diffractometer | 3175 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2686 reflections with I > 2σ(I) |
Tmin = 0.901, Tmax = 0.979 | Rint = 0.022 |
12897 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 1 restraint |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.23 e Å−3 |
3175 reflections | Δρmin = −0.23 e Å−3 |
185 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | −0.03631 (7) | 0.20770 (12) | 0.36470 (6) | 0.0392 (2) | |
O2 | 0.32157 (9) | 0.56190 (11) | 0.51403 (6) | 0.0384 (2) | |
N1 | 0.26191 (9) | 0.43083 (12) | 0.38154 (6) | 0.0293 (2) | |
N2 | 0.11807 (8) | 0.19261 (12) | 0.48395 (6) | 0.0280 (2) | |
C1 | 0.07223 (10) | 0.19025 (14) | 0.39558 (8) | 0.0283 (2) | |
C2 | 0.15986 (10) | 0.16141 (14) | 0.33568 (7) | 0.0270 (2) | |
C3 | 0.14642 (11) | 0.01939 (15) | 0.28107 (7) | 0.0313 (3) | |
H3 | 0.0832 | −0.0590 | 0.2833 | 0.038* | |
C4 | 0.22439 (12) | −0.00839 (16) | 0.22364 (8) | 0.0346 (3) | |
H4 | 0.2150 | −0.1059 | 0.1869 | 0.042* | |
C5 | 0.31624 (12) | 0.10641 (17) | 0.21977 (7) | 0.0356 (3) | |
H5 | 0.3706 | 0.0864 | 0.1811 | 0.043* | |
C6 | 0.32876 (11) | 0.25014 (15) | 0.27217 (8) | 0.0323 (3) | |
H6 | 0.3905 | 0.3299 | 0.2683 | 0.039* | |
C7 | 0.25127 (10) | 0.27809 (14) | 0.33037 (7) | 0.0271 (2) | |
C8 | 0.23206 (13) | 0.59028 (16) | 0.33401 (9) | 0.0410 (3) | 0.75 |
H8A | 0.2291 | 0.6813 | 0.3766 | 0.049* | 0.75 |
H8B | 0.1530 | 0.5801 | 0.2939 | 0.049* | 0.75 |
H8C | 0.2941 | 0.6162 | 0.2996 | 0.049* | 0.75 |
C8' | 0.23206 (13) | 0.59028 (16) | 0.33401 (9) | 0.0410 (3) | 0.25 |
H8D | 0.2974 | 0.6720 | 0.3534 | 0.049* | 0.25 |
H8E | 0.1562 | 0.6349 | 0.3466 | 0.049* | 0.25 |
H8F | 0.2226 | 0.5707 | 0.2702 | 0.049* | 0.25 |
C9 | 0.30500 (10) | 0.43187 (14) | 0.47035 (7) | 0.0271 (2) | |
C10 | 0.33394 (10) | 0.26308 (13) | 0.51321 (7) | 0.0239 (2) | |
C11 | 0.45333 (10) | 0.22278 (15) | 0.55095 (7) | 0.0272 (2) | |
H11 | 0.5166 | 0.2994 | 0.5460 | 0.033* | |
C12 | 0.48022 (10) | 0.07159 (15) | 0.59559 (7) | 0.0304 (3) | |
H12 | 0.5619 | 0.0443 | 0.6210 | 0.036* | |
C13 | 0.38820 (11) | −0.04021 (15) | 0.60338 (7) | 0.0309 (3) | |
H13 | 0.4071 | −0.1439 | 0.6342 | 0.037* | |
C14 | 0.26895 (11) | −0.00143 (14) | 0.56646 (7) | 0.0291 (2) | |
H14 | 0.2059 | −0.0777 | 0.5723 | 0.035* | |
C15 | 0.24198 (9) | 0.14978 (14) | 0.52073 (7) | 0.0243 (2) | |
C16 | 0.03856 (11) | 0.22890 (17) | 0.54596 (9) | 0.0363 (3) | 0.65 |
H16A | −0.0385 | 0.2743 | 0.5134 | 0.044* | 0.65 |
H16B | 0.0774 | 0.3121 | 0.5897 | 0.044* | 0.65 |
H16C | 0.0236 | 0.1246 | 0.5763 | 0.044* | 0.65 |
C16' | 0.03856 (11) | 0.22890 (17) | 0.54596 (9) | 0.0363 (3) | 0.35 |
H16D | −0.0348 | 0.1596 | 0.5309 | 0.044* | 0.35 |
H16E | 0.0163 | 0.3488 | 0.5421 | 0.044* | 0.35 |
H16F | 0.0810 | 0.2026 | 0.6064 | 0.044* | 0.35 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0249 (4) | 0.0477 (5) | 0.0415 (5) | −0.0008 (4) | −0.0015 (3) | 0.0076 (4) |
O2 | 0.0516 (6) | 0.0251 (4) | 0.0385 (5) | −0.0088 (4) | 0.0088 (4) | −0.0029 (3) |
N1 | 0.0320 (5) | 0.0229 (5) | 0.0309 (5) | −0.0034 (4) | 0.0012 (4) | 0.0057 (4) |
N2 | 0.0235 (4) | 0.0306 (5) | 0.0297 (5) | −0.0045 (4) | 0.0045 (4) | 0.0013 (4) |
C1 | 0.0257 (5) | 0.0237 (5) | 0.0330 (6) | −0.0039 (4) | 0.0004 (4) | 0.0043 (4) |
C2 | 0.0271 (5) | 0.0272 (5) | 0.0235 (5) | −0.0012 (4) | −0.0029 (4) | 0.0057 (4) |
C3 | 0.0334 (6) | 0.0278 (6) | 0.0283 (5) | −0.0026 (4) | −0.0045 (4) | 0.0047 (4) |
C4 | 0.0440 (7) | 0.0319 (6) | 0.0242 (5) | 0.0037 (5) | −0.0023 (5) | 0.0014 (5) |
C5 | 0.0417 (7) | 0.0416 (7) | 0.0232 (5) | 0.0062 (5) | 0.0055 (5) | 0.0074 (5) |
C6 | 0.0341 (6) | 0.0349 (6) | 0.0267 (5) | −0.0022 (5) | 0.0036 (4) | 0.0108 (5) |
C7 | 0.0302 (5) | 0.0257 (5) | 0.0226 (5) | −0.0011 (4) | −0.0014 (4) | 0.0064 (4) |
C8 | 0.0490 (8) | 0.0270 (6) | 0.0428 (7) | −0.0010 (5) | −0.0012 (6) | 0.0110 (5) |
C8' | 0.0490 (8) | 0.0270 (6) | 0.0428 (7) | −0.0010 (5) | −0.0012 (6) | 0.0110 (5) |
C9 | 0.0255 (5) | 0.0248 (5) | 0.0311 (6) | −0.0062 (4) | 0.0055 (4) | 0.0019 (4) |
C10 | 0.0268 (5) | 0.0245 (5) | 0.0204 (5) | −0.0039 (4) | 0.0044 (4) | −0.0015 (4) |
C11 | 0.0253 (5) | 0.0316 (6) | 0.0245 (5) | −0.0051 (4) | 0.0047 (4) | −0.0022 (4) |
C12 | 0.0277 (5) | 0.0365 (6) | 0.0257 (5) | 0.0022 (4) | 0.0024 (4) | −0.0006 (4) |
C13 | 0.0392 (6) | 0.0279 (6) | 0.0247 (5) | 0.0016 (5) | 0.0045 (4) | 0.0038 (4) |
C14 | 0.0333 (6) | 0.0277 (6) | 0.0258 (5) | −0.0071 (4) | 0.0046 (4) | 0.0016 (4) |
C15 | 0.0244 (5) | 0.0262 (5) | 0.0217 (5) | −0.0042 (4) | 0.0031 (4) | −0.0008 (4) |
C16 | 0.0297 (6) | 0.0417 (7) | 0.0390 (7) | −0.0057 (5) | 0.0107 (5) | −0.0040 (5) |
C16' | 0.0297 (6) | 0.0417 (7) | 0.0390 (7) | −0.0057 (5) | 0.0107 (5) | −0.0040 (5) |
O1—C1 | 1.2280 (13) | C6—H6 | 0.9500 |
O2—C9 | 1.2229 (14) | C8—H8A | 0.9800 |
N1—C9 | 1.3569 (15) | C8—H8B | 0.9800 |
N1—C7 | 1.4346 (15) | C8—H8C | 0.9800 |
N1—C8 | 1.4635 (14) | C9—C10 | 1.4964 (15) |
N2—C1 | 1.3558 (15) | C10—C11 | 1.3913 (15) |
N2—C15 | 1.4380 (14) | C10—C15 | 1.3926 (14) |
N2—C16 | 1.4642 (15) | C11—C12 | 1.3827 (16) |
C1—C2 | 1.4990 (16) | C11—H11 | 0.9500 |
C2—C3 | 1.3936 (16) | C12—C13 | 1.3867 (17) |
C2—C7 | 1.3980 (15) | C12—H12 | 0.9500 |
C3—C4 | 1.3846 (18) | C13—C14 | 1.3844 (17) |
C3—H3 | 0.9500 | C13—H13 | 0.9500 |
C4—C5 | 1.3874 (19) | C14—C15 | 1.3906 (15) |
C4—H4 | 0.9500 | C14—H14 | 0.9500 |
C5—C6 | 1.3854 (18) | C16—H16A | 0.9800 |
C5—H5 | 0.9500 | C16—H16B | 0.9800 |
C6—C7 | 1.3897 (17) | C16—H16C | 0.9800 |
C9—N1—C7 | 122.20 (9) | N1—C8—H8A | 109.5 |
C9—N1—C8 | 119.94 (10) | N1—C8—H8B | 109.5 |
C7—N1—C8 | 117.74 (9) | N1—C8—H8C | 109.5 |
C1—N2—C15 | 122.43 (9) | O2—C9—N1 | 122.97 (10) |
C1—N2—C16 | 119.90 (10) | O2—C9—C10 | 120.80 (10) |
C15—N2—C16 | 117.55 (9) | N1—C9—C10 | 116.21 (9) |
O1—C1—N2 | 122.43 (11) | C11—C10—C15 | 119.42 (10) |
O1—C1—C2 | 120.47 (10) | C11—C10—C9 | 119.71 (9) |
N2—C1—C2 | 117.09 (9) | C15—C10—C9 | 120.75 (10) |
C3—C2—C7 | 119.27 (11) | C12—C11—C10 | 120.20 (10) |
C3—C2—C1 | 119.31 (10) | C12—C11—H11 | 119.9 |
C7—C2—C1 | 121.35 (10) | C10—C11—H11 | 119.9 |
C4—C3—C2 | 120.54 (11) | C11—C12—C13 | 120.13 (10) |
C4—C3—H3 | 119.7 | C11—C12—H12 | 119.9 |
C2—C3—H3 | 119.7 | C13—C12—H12 | 119.9 |
C3—C4—C5 | 119.91 (11) | C14—C13—C12 | 120.29 (11) |
C3—C4—H4 | 120.0 | C14—C13—H13 | 119.9 |
C5—C4—H4 | 120.0 | C12—C13—H13 | 119.9 |
C6—C5—C4 | 120.11 (12) | C13—C14—C15 | 119.60 (10) |
C6—C5—H5 | 119.9 | C13—C14—H14 | 120.2 |
C4—C5—H5 | 119.9 | C15—C14—H14 | 120.2 |
C5—C6—C7 | 120.21 (11) | C14—C15—C10 | 120.36 (10) |
C5—C6—H6 | 119.9 | C14—C15—N2 | 119.89 (9) |
C7—C6—H6 | 119.9 | C10—C15—N2 | 119.71 (10) |
C6—C7—C2 | 119.94 (11) | N2—C16—H16A | 109.5 |
C6—C7—N1 | 119.66 (10) | N2—C16—H16B | 109.5 |
C2—C7—N1 | 120.34 (10) | N2—C16—H16C | 109.5 |
C15—N2—C1—O1 | 171.43 (10) | C7—N1—C9—O2 | 175.40 (11) |
C16—N2—C1—O1 | −4.45 (17) | C8—N1—C9—O2 | −0.55 (18) |
C15—N2—C1—C2 | −7.30 (15) | C7—N1—C9—C10 | −3.60 (15) |
C16—N2—C1—C2 | 176.82 (10) | C8—N1—C9—C10 | −179.55 (10) |
O1—C1—C2—C3 | −60.48 (15) | O2—C9—C10—C11 | −64.70 (15) |
N2—C1—C2—C3 | 118.28 (11) | N1—C9—C10—C11 | 114.32 (11) |
O1—C1—C2—C7 | 116.44 (12) | O2—C9—C10—C15 | 111.25 (12) |
N2—C1—C2—C7 | −64.81 (14) | N1—C9—C10—C15 | −69.72 (14) |
C7—C2—C3—C4 | 1.56 (16) | C15—C10—C11—C12 | −0.08 (16) |
C1—C2—C3—C4 | 178.54 (10) | C9—C10—C11—C12 | 175.93 (10) |
C2—C3—C4—C5 | −0.46 (17) | C10—C11—C12—C13 | −0.36 (16) |
C3—C4—C5—C6 | −1.08 (17) | C11—C12—C13—C14 | 0.11 (17) |
C4—C5—C6—C7 | 1.52 (17) | C12—C13—C14—C15 | 0.59 (17) |
C5—C6—C7—C2 | −0.41 (16) | C13—C14—C15—C10 | −1.03 (16) |
C5—C6—C7—N1 | −177.39 (10) | C13—C14—C15—N2 | −178.59 (10) |
C3—C2—C7—C6 | −1.12 (15) | C11—C10—C15—C14 | 0.78 (16) |
C1—C2—C7—C6 | −178.04 (10) | C9—C10—C15—C14 | −175.18 (10) |
C3—C2—C7—N1 | 175.84 (9) | C11—C10—C15—N2 | 178.34 (9) |
C1—C2—C7—N1 | −1.08 (15) | C9—C10—C15—N2 | 2.37 (15) |
C9—N1—C7—C6 | −109.40 (12) | C1—N2—C15—C14 | −108.33 (12) |
C8—N1—C7—C6 | 66.63 (14) | C16—N2—C15—C14 | 67.64 (14) |
C9—N1—C7—C2 | 73.63 (14) | C1—N2—C15—C10 | 74.10 (14) |
C8—N1—C7—C2 | −110.33 (12) | C16—N2—C15—C10 | −109.93 (12) |
Experimental details
Crystal data | |
Chemical formula | C16H14N2O2 |
Mr | 266.29 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 11.2715 (10), 7.9113 (7), 15.4100 (14) |
β (°) | 101.611 (1) |
V (Å3) | 1346.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.55 × 0.42 × 0.24 |
Data collection | |
Diffractometer | Bruker 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.901, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12897, 3175, 2686 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.104, 1.04 |
No. of reflections | 3175 |
No. of parameters | 185 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.23 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001) and SHELXTL (Bruker, 2003), modiCIFer (Version Dec-16-2005; Guzei, 2005).
Acknowledgements
The authors thank the Australian Research Council for a Discovery Project grant to ACT (grant No. DP0345180), and Macquarie University for the award of a Macquarie University Research Development grant to ACT and the award of a PhD scholarship to ABM.
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Several structures of the unsubstituted dianthranilide (i.e., lacking methyl groups on the nitrogen atoms) are present in the literature, including ethanol, DMF and pyridine solvates of racemic material (Gordon-Wylie et al., 2004) as well as a DMSO solvate of racemic material, unsolvated racemate and a DMSO solvate of enantiomerically pure crystals (Olszewska et al., 2004).
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are within normal ranges. When the crystal structure was solved, the two methyl groups were found to be disordered. The dihedral angle between the two benzene rings is 75.57 (3)°.
The X-ray crystal structures of three N,N'-disubstituted dianthranilides have also been reported and in all cases they have a smaller dihedral angle between the two aryl rings of the dianthranilide in comparison with the structures of the unsubstituted compounds. The N,N'-di[1-(N-t-butylcarbamoyl)-1-(cyclohexyl)- methyl] (Ebert et al., 1998), N,N'-dibenzyl (Nonnenmacher et al., 2000) and N,N'-dicamphanoyl derivatives (Olszewska et al., 2004) have dihedral angles of 78.2, 83.9 and 77.5°, respectively.