Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043863/bt2500sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043863/bt2500Isup2.hkl |
CCDC reference: 663753
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.059
- wR factor = 0.139
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc.
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C14 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C15 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C17 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C20 = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound was prepared from norbornene dianhydride and 4-azobenzene according to the literature method (Tian et al., 2007). Single crystals were obtained by slow evaporation of a ethanol solution.
All hydrogen atoms were located in a difference Fourier map, but they were constrained to ride on their parent atoms with C—Haryl, C—Hmethylene and C—Hmethine-H distances of 0.93, 0.97 and 0.98 Å, respectively. Uiso(H) was set to 1.2Ueq(C). The two N atoms of the azo moiety are disordered over two sites with occupancies of 0.681 (12) and 0.319 (12). The C—N bond distances of the disordered N atoms were restrained to be equal within 0.01 Å.
The family of azobenzenes has been investigated intensively due to the their remarkable photochemically induced trans to cis isomerism. Azo polymers are of interest in various fields (Zhao et al., 1999). As a part of our investigation of preparing azo polymers, we report the crystal structure of the title compound (Fig. 1).
Bond lengths and angles of the norbornene moiety are similar to those in other norbornene derivatives (Tian et al., 2007). By means of C–H···O hydrogen bonds, the molecules are linked into a ribbon. (Tab. 1, Fig. 2). The two aromatic rings are almost coplanar [dihedral angle 9.25 (10)°]. The dihedral angle between the rings C13—C14—C15—C16—N13 and C7—C8—C9—C10—C11—C12 is 64.32 (7)° (Fig. 1).
For related literature, see: Tian et al. (2007); Zhao et al. (1999).
Data collection: SMART (Bruker 2001); cell refinement: SMART (Bruker 2001); data reduction: SAINT (Bruker 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2001); software used to prepare material for publication: SHELXTL (Bruker 2001).
Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. Crystal packing of the title compound. |
C21H17N3O2 | F(000) = 1440 |
Mr = 343.38 | Dx = 1.318 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 1899 reflections |
a = 25.190 (2) Å | θ = 3.2–20.8° |
b = 6.5076 (5) Å | µ = 0.09 mm−1 |
c = 24.2792 (19) Å | T = 292 K |
β = 119.567 (1)° | Block, red |
V = 3461.7 (5) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 8 |
CCD area detector diffractometer | 2363 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.041 |
Graphite monochromator | θmax = 27.0°, θmin = 1.9° |
φ and ω scans | h = −32→32 |
13859 measured reflections | k = −8→7 |
3778 independent reflections | l = −31→29 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0477P)2 + 1.3571P] where P = (Fo2 + 2Fc2)/3 |
3778 reflections | (Δ/σ)max = 0.001 |
254 parameters | Δρmax = 0.16 e Å−3 |
2 restraints | Δρmin = −0.18 e Å−3 |
C21H17N3O2 | V = 3461.7 (5) Å3 |
Mr = 343.38 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 25.190 (2) Å | µ = 0.09 mm−1 |
b = 6.5076 (5) Å | T = 292 K |
c = 24.2792 (19) Å | 0.20 × 0.20 × 0.10 mm |
β = 119.567 (1)° |
CCD area detector diffractometer | 2363 reflections with I > 2σ(I) |
13859 measured reflections | Rint = 0.041 |
3778 independent reflections |
R[F2 > 2σ(F2)] = 0.059 | 2 restraints |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.16 e Å−3 |
3778 reflections | Δρmin = −0.18 e Å−3 |
254 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) | |
C1 | 0.08004 (11) | 0.3958 (5) | 0.69015 (11) | 0.0732 (7) | |
H1 | 0.1091 | 0.3373 | 0.7281 | 0.088* | |
C2 | 0.06036 (11) | 0.2911 (4) | 0.63479 (12) | 0.0678 (7) | |
H2 | 0.0767 | 0.1626 | 0.6351 | 0.081* | |
C3 | 0.01680 (10) | 0.3736 (4) | 0.57875 (10) | 0.0602 (6) | |
H3 | 0.0032 | 0.3005 | 0.5412 | 0.072* | |
C4 | −0.00677 (10) | 0.5639 (4) | 0.57788 (11) | 0.0618 (6) | |
H4 | −0.0363 | 0.6205 | 0.5398 | 0.074* | |
C5 | 0.01360 (11) | 0.6716 (4) | 0.63394 (13) | 0.0679 (7) | |
H5 | −0.0022 | 0.8010 | 0.6337 | 0.081* | |
C6 | 0.05724 (11) | 0.5864 (4) | 0.68998 (11) | 0.0688 (7) | |
C7 | 0.09946 (11) | 0.8942 (5) | 0.82488 (11) | 0.0725 (8) | |
C8 | 0.13603 (12) | 0.7963 (4) | 0.88181 (12) | 0.0699 (7) | |
H8 | 0.1504 | 0.6646 | 0.8821 | 0.084* | |
C9 | 0.15139 (10) | 0.8937 (3) | 0.93864 (10) | 0.0558 (6) | |
H9 | 0.1767 | 0.8295 | 0.9771 | 0.067* | |
C10 | 0.12857 (8) | 1.0860 (3) | 0.93703 (9) | 0.0430 (5) | |
C11 | 0.09270 (9) | 1.1846 (4) | 0.88030 (9) | 0.0554 (6) | |
H11 | 0.0779 | 1.3159 | 0.8798 | 0.067* | |
C12 | 0.07893 (10) | 1.0891 (5) | 0.82462 (10) | 0.0707 (7) | |
H12 | 0.0555 | 1.1570 | 0.7864 | 0.085* | |
C13 | 0.12212 (9) | 1.1082 (3) | 1.03599 (9) | 0.0504 (5) | |
C14 | 0.14222 (9) | 1.2552 (3) | 1.09033 (9) | 0.0522 (6) | |
H14 | 0.1070 | 1.3146 | 1.0914 | 0.063* | |
C15 | 0.17851 (9) | 1.4214 (3) | 1.07873 (9) | 0.0522 (5) | |
H15 | 0.1604 | 1.5573 | 1.0756 | 0.063* | |
C16 | 0.17573 (9) | 1.3640 (3) | 1.01730 (9) | 0.0470 (5) | |
C17 | 0.18936 (10) | 1.1676 (4) | 1.15637 (9) | 0.0629 (6) | |
H17 | 0.1725 | 1.0893 | 1.1787 | 0.075* | |
C18 | 0.23697 (11) | 1.0607 (4) | 1.14686 (10) | 0.0648 (7) | |
H18 | 0.2435 | 0.9197 | 1.1484 | 0.078* | |
C19 | 0.26790 (10) | 1.2020 (4) | 1.13589 (10) | 0.0639 (6) | |
H19 | 0.2998 | 1.1786 | 1.1278 | 0.077* | |
C20 | 0.24259 (10) | 1.4069 (4) | 1.13884 (10) | 0.0607 (6) | |
H20 | 0.2696 | 1.5250 | 1.1471 | 0.073* | |
C21 | 0.22356 (11) | 1.3637 (4) | 1.18850 (11) | 0.0750 (7) | |
H21A | 0.2580 | 1.3396 | 1.2304 | 0.090* | |
H21B | 0.1972 | 1.4693 | 1.1902 | 0.090* | |
N1 | 0.08481 (19) | 0.6515 (8) | 0.7579 (2) | 0.0587 (14) | 0.681 (12) |
N2 | 0.07375 (17) | 0.8321 (8) | 0.75791 (19) | 0.0555 (14) | 0.681 (12) |
N1' | 0.0608 (4) | 0.7694 (12) | 0.7278 (5) | 0.053 (3) | 0.319 (12) |
N2' | 0.0990 (4) | 0.7111 (15) | 0.7852 (4) | 0.054 (3) | 0.319 (12) |
N3 | 0.14098 (7) | 1.1850 (2) | 0.99484 (7) | 0.0426 (4) | |
O1 | 0.09449 (8) | 0.9498 (3) | 1.02764 (7) | 0.0773 (5) | |
O2 | 0.19937 (8) | 1.4485 (2) | 0.99100 (8) | 0.0686 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0621 (14) | 0.108 (2) | 0.0493 (14) | 0.0060 (14) | 0.0272 (11) | −0.0015 (14) |
C2 | 0.0740 (16) | 0.0677 (16) | 0.0706 (17) | 0.0052 (13) | 0.0426 (14) | −0.0057 (13) |
C3 | 0.0613 (13) | 0.0777 (17) | 0.0491 (13) | −0.0168 (12) | 0.0331 (11) | −0.0194 (12) |
C4 | 0.0522 (13) | 0.0806 (17) | 0.0563 (14) | −0.0011 (12) | 0.0296 (11) | 0.0076 (13) |
C5 | 0.0664 (15) | 0.0599 (15) | 0.101 (2) | −0.0058 (12) | 0.0591 (15) | −0.0159 (14) |
C6 | 0.0588 (14) | 0.099 (2) | 0.0625 (15) | −0.0196 (14) | 0.0404 (13) | −0.0319 (15) |
C7 | 0.0657 (15) | 0.113 (2) | 0.0516 (15) | −0.0391 (15) | 0.0388 (13) | −0.0333 (15) |
C8 | 0.0912 (18) | 0.0579 (15) | 0.0824 (18) | −0.0183 (13) | 0.0594 (16) | −0.0232 (14) |
C9 | 0.0693 (14) | 0.0482 (13) | 0.0553 (13) | −0.0041 (11) | 0.0349 (11) | −0.0018 (11) |
C10 | 0.0445 (10) | 0.0465 (12) | 0.0406 (11) | −0.0080 (9) | 0.0229 (9) | −0.0039 (9) |
C11 | 0.0469 (11) | 0.0739 (15) | 0.0454 (12) | 0.0032 (10) | 0.0227 (10) | 0.0055 (11) |
C12 | 0.0510 (13) | 0.119 (2) | 0.0402 (12) | −0.0088 (14) | 0.0210 (10) | −0.0045 (14) |
C13 | 0.0465 (11) | 0.0610 (14) | 0.0441 (11) | −0.0087 (10) | 0.0226 (9) | −0.0034 (10) |
C14 | 0.0428 (11) | 0.0709 (15) | 0.0468 (12) | 0.0027 (10) | 0.0251 (9) | −0.0102 (10) |
C15 | 0.0613 (13) | 0.0399 (12) | 0.0546 (12) | 0.0064 (10) | 0.0279 (10) | −0.0065 (10) |
C16 | 0.0519 (12) | 0.0352 (11) | 0.0517 (12) | 0.0022 (9) | 0.0238 (10) | 0.0038 (9) |
C17 | 0.0655 (14) | 0.0846 (17) | 0.0416 (12) | −0.0100 (13) | 0.0286 (11) | −0.0020 (12) |
C18 | 0.0693 (15) | 0.0596 (15) | 0.0498 (13) | 0.0124 (12) | 0.0174 (11) | 0.0061 (11) |
C19 | 0.0440 (12) | 0.0839 (18) | 0.0554 (13) | 0.0080 (12) | 0.0181 (10) | −0.0037 (13) |
C20 | 0.0565 (13) | 0.0640 (15) | 0.0551 (13) | −0.0147 (11) | 0.0226 (11) | −0.0184 (11) |
C21 | 0.0697 (15) | 0.099 (2) | 0.0496 (13) | −0.0036 (14) | 0.0244 (12) | −0.0237 (14) |
N1 | 0.061 (3) | 0.067 (3) | 0.047 (3) | 0.010 (2) | 0.025 (2) | 0.000 (2) |
N2 | 0.057 (2) | 0.062 (3) | 0.046 (3) | −0.0013 (17) | 0.025 (2) | 0.0017 (19) |
N1' | 0.052 (4) | 0.067 (6) | 0.030 (5) | 0.005 (4) | 0.014 (4) | −0.007 (4) |
N2' | 0.056 (5) | 0.068 (7) | 0.024 (5) | 0.003 (4) | 0.010 (4) | −0.009 (4) |
N3 | 0.0480 (9) | 0.0428 (10) | 0.0373 (8) | −0.0031 (7) | 0.0213 (7) | −0.0001 (7) |
O1 | 0.0894 (12) | 0.0902 (13) | 0.0616 (10) | −0.0448 (10) | 0.0443 (9) | −0.0165 (9) |
O2 | 0.0898 (11) | 0.0520 (9) | 0.0711 (10) | −0.0171 (8) | 0.0450 (9) | 0.0034 (8) |
C1—C2 | 1.363 (3) | C12—H12 | 0.9300 |
C1—C6 | 1.366 (4) | C13—O1 | 1.204 (2) |
C1—H1 | 0.9300 | C13—N3 | 1.393 (2) |
C2—C3 | 1.368 (3) | C13—C14 | 1.501 (3) |
C2—H2 | 0.9300 | C14—C15 | 1.529 (3) |
C3—C4 | 1.369 (3) | C14—C17 | 1.558 (3) |
C3—H3 | 0.9300 | C14—H14 | 0.9800 |
C4—C5 | 1.385 (3) | C15—C16 | 1.505 (3) |
C4—H4 | 0.9300 | C15—C20 | 1.555 (3) |
C5—C6 | 1.375 (3) | C15—H15 | 0.9800 |
C5—H5 | 0.9300 | C16—O2 | 1.200 (2) |
C6—N1' | 1.480 (7) | C16—N3 | 1.397 (2) |
C6—N1 | 1.500 (5) | C17—C18 | 1.499 (3) |
C7—C12 | 1.369 (4) | C17—C21 | 1.522 (3) |
C7—C8 | 1.381 (4) | C17—H17 | 0.9800 |
C7—N2 | 1.479 (5) | C18—C19 | 1.314 (3) |
C7—N2' | 1.529 (9) | C18—H18 | 0.9300 |
C8—C9 | 1.389 (3) | C19—C20 | 1.495 (3) |
C8—H8 | 0.9300 | C19—H19 | 0.9300 |
C9—C10 | 1.370 (3) | C20—C21 | 1.528 (3) |
C9—H9 | 0.9300 | C20—H20 | 0.9800 |
C10—C11 | 1.377 (3) | C21—H21A | 0.9700 |
C10—N3 | 1.432 (2) | C21—H21B | 0.9700 |
C11—C12 | 1.368 (3) | N1—N2 | 1.207 (9) |
C11—H11 | 0.9300 | N1'—N2' | 1.298 (18) |
C2—C1—C6 | 120.2 (2) | C15—C14—C17 | 103.14 (16) |
C2—C1—H1 | 119.9 | C13—C14—H14 | 110.9 |
C6—C1—H1 | 119.9 | C15—C14—H14 | 110.9 |
C1—C2—C3 | 120.5 (2) | C17—C14—H14 | 110.9 |
C1—C2—H2 | 119.7 | C16—C15—C14 | 105.49 (16) |
C3—C2—H2 | 119.7 | C16—C15—C20 | 115.72 (17) |
C2—C3—C4 | 120.0 (2) | C14—C15—C20 | 102.83 (17) |
C2—C3—H3 | 120.0 | C16—C15—H15 | 110.8 |
C4—C3—H3 | 120.0 | C14—C15—H15 | 110.8 |
C3—C4—C5 | 119.7 (2) | C20—C15—H15 | 110.8 |
C3—C4—H4 | 120.2 | O2—C16—N3 | 123.68 (19) |
C5—C4—H4 | 120.2 | O2—C16—C15 | 128.39 (19) |
C6—C5—C4 | 119.7 (2) | N3—C16—C15 | 107.92 (17) |
C6—C5—H5 | 120.1 | C18—C17—C21 | 100.03 (19) |
C4—C5—H5 | 120.1 | C18—C17—C14 | 105.81 (17) |
C1—C6—C5 | 119.9 (2) | C21—C17—C14 | 99.88 (18) |
C1—C6—N1' | 146.4 (5) | C18—C17—H17 | 116.2 |
C5—C6—N1' | 93.7 (5) | C21—C17—H17 | 116.2 |
C1—C6—N1 | 106.7 (3) | C14—C17—H17 | 116.2 |
C5—C6—N1 | 133.2 (3) | C19—C18—C17 | 107.8 (2) |
C12—C7—C8 | 119.7 (2) | C19—C18—H18 | 126.1 |
C12—C7—N2 | 106.8 (3) | C17—C18—H18 | 126.1 |
C8—C7—N2 | 133.5 (3) | C18—C19—C20 | 107.7 (2) |
C12—C7—N2' | 146.5 (5) | C18—C19—H19 | 126.1 |
C8—C7—N2' | 93.8 (5) | C20—C19—H19 | 126.1 |
C7—C8—C9 | 120.4 (2) | C19—C20—C21 | 100.4 (2) |
C7—C8—H8 | 119.8 | C19—C20—C15 | 106.20 (17) |
C9—C8—H8 | 119.8 | C21—C20—C15 | 99.63 (18) |
C10—C9—C8 | 118.8 (2) | C19—C20—H20 | 116.1 |
C10—C9—H9 | 120.6 | C21—C20—H20 | 116.1 |
C8—C9—H9 | 120.6 | C15—C20—H20 | 116.1 |
C9—C10—C11 | 120.9 (2) | C17—C21—C20 | 93.94 (17) |
C9—C10—N3 | 119.84 (18) | C17—C21—H21A | 112.9 |
C11—C10—N3 | 119.27 (18) | C20—C21—H21A | 112.9 |
C12—C11—C10 | 119.8 (2) | C17—C21—H21B | 112.9 |
C12—C11—H11 | 120.1 | C20—C21—H21B | 112.9 |
C10—C11—H11 | 120.1 | H21A—C21—H21B | 110.4 |
C11—C12—C7 | 120.4 (2) | N2—N1—C6 | 107.1 (4) |
C11—C12—H12 | 119.8 | N1—N2—C7 | 106.9 (4) |
C7—C12—H12 | 119.8 | N2'—N1'—C6 | 102.5 (7) |
O1—C13—N3 | 124.03 (19) | N1'—N2'—C7 | 102.7 (8) |
O1—C13—C14 | 127.59 (19) | C13—N3—C16 | 112.89 (16) |
N3—C13—C14 | 108.38 (18) | C13—N3—C10 | 123.70 (16) |
C13—C14—C15 | 105.19 (16) | C16—N3—C10 | 123.35 (16) |
C13—C14—C17 | 115.26 (18) | ||
C6—C1—C2—C3 | −1.3 (4) | C14—C17—C18—C19 | 69.5 (2) |
C1—C2—C3—C4 | 0.9 (4) | C17—C18—C19—C20 | 0.9 (2) |
C2—C3—C4—C5 | −0.2 (3) | C18—C19—C20—C21 | 32.3 (2) |
C3—C4—C5—C6 | −0.1 (3) | C18—C19—C20—C15 | −71.1 (2) |
C2—C1—C6—C5 | 1.0 (4) | C16—C15—C20—C19 | −48.1 (3) |
C2—C1—C6—N1' | −174.7 (6) | C14—C15—C20—C19 | 66.3 (2) |
C2—C1—C6—N1 | 176.3 (3) | C16—C15—C20—C21 | −152.03 (19) |
C4—C5—C6—C1 | −0.3 (4) | C14—C15—C20—C21 | −37.6 (2) |
C4—C5—C6—N1' | 177.3 (3) | C18—C17—C21—C20 | 49.8 (2) |
C4—C5—C6—N1 | −174.1 (3) | C14—C17—C21—C20 | −58.39 (19) |
C12—C7—C8—C9 | 0.8 (3) | C19—C20—C21—C17 | −49.44 (19) |
N2—C7—C8—C9 | −177.6 (3) | C15—C20—C21—C17 | 59.2 (2) |
N2'—C7—C8—C9 | −178.1 (4) | C1—C6—N1—N2 | 168.1 (3) |
C7—C8—C9—C10 | 1.4 (3) | C5—C6—N1—N2 | −17.6 (5) |
C8—C9—C10—C11 | −2.2 (3) | N1'—C6—N1—N2 | −4.2 (6) |
C8—C9—C10—N3 | 176.58 (18) | C6—N1—N2—C7 | 178.4 (3) |
C9—C10—C11—C12 | 0.8 (3) | C12—C7—N2—N1 | −170.9 (3) |
N3—C10—C11—C12 | −177.98 (18) | C8—C7—N2—N1 | 7.7 (5) |
C10—C11—C12—C7 | 1.5 (3) | N2'—C7—N2—N1 | 8.4 (6) |
C8—C7—C12—C11 | −2.2 (3) | C1—C6—N1'—N2' | −7.1 (10) |
N2—C7—C12—C11 | 176.6 (2) | C5—C6—N1'—N2' | 176.6 (6) |
N2'—C7—C12—C11 | 175.8 (7) | N1—C6—N1'—N2' | 6.4 (6) |
O1—C13—C14—C15 | 176.6 (2) | C6—N1'—N2'—C7 | −176.3 (5) |
N3—C13—C14—C15 | −3.3 (2) | C12—C7—N2'—N1' | −4.1 (11) |
O1—C13—C14—C17 | 63.8 (3) | C8—C7—N2'—N1' | 174.2 (6) |
N3—C13—C14—C17 | −116.16 (19) | N2—C7—N2'—N1' | −5.3 (5) |
C13—C14—C15—C16 | 1.6 (2) | O1—C13—N3—C16 | −175.9 (2) |
C17—C14—C15—C16 | 122.73 (17) | C14—C13—N3—C16 | 4.0 (2) |
C13—C14—C15—C20 | −120.09 (17) | O1—C13—N3—C10 | 1.3 (3) |
C17—C14—C15—C20 | 1.1 (2) | C14—C13—N3—C10 | −178.78 (16) |
C14—C15—C16—O2 | −177.8 (2) | O2—C16—N3—C13 | 175.6 (2) |
C20—C15—C16—O2 | −64.9 (3) | C15—C16—N3—C13 | −2.9 (2) |
C14—C15—C16—N3 | 0.6 (2) | O2—C16—N3—C10 | −1.7 (3) |
C20—C15—C16—N3 | 113.55 (19) | C15—C16—N3—C10 | 179.84 (16) |
C13—C14—C17—C18 | 46.5 (2) | C9—C10—N3—C13 | −62.1 (3) |
C15—C14—C17—C18 | −67.5 (2) | C11—C10—N3—C13 | 116.6 (2) |
C13—C14—C17—C21 | 150.03 (18) | C9—C10—N3—C16 | 114.8 (2) |
C15—C14—C17—C21 | 36.0 (2) | C11—C10—N3—C16 | −66.4 (2) |
C21—C17—C18—C19 | −33.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O2i | 0.93 | 2.53 | 3.155 (3) | 125 |
Symmetry code: (i) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C21H17N3O2 |
Mr | 343.38 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 292 |
a, b, c (Å) | 25.190 (2), 6.5076 (5), 24.2792 (19) |
β (°) | 119.567 (1) |
V (Å3) | 3461.7 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | CCD area detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13859, 3778, 2363 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.139, 1.06 |
No. of reflections | 3778 |
No. of parameters | 254 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.18 |
Computer programs: SMART (Bruker 2001), SAINT (Bruker 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O2i | 0.93 | 2.53 | 3.155 (3) | 124.9 |
Symmetry code: (i) x, y−1, z. |
The family of azobenzenes has been investigated intensively due to the their remarkable photochemically induced trans to cis isomerism. Azo polymers are of interest in various fields (Zhao et al., 1999). As a part of our investigation of preparing azo polymers, we report the crystal structure of the title compound (Fig. 1).
Bond lengths and angles of the norbornene moiety are similar to those in other norbornene derivatives (Tian et al., 2007). By means of C–H···O hydrogen bonds, the molecules are linked into a ribbon. (Tab. 1, Fig. 2). The two aromatic rings are almost coplanar [dihedral angle 9.25 (10)°]. The dihedral angle between the rings C13—C14—C15—C16—N13 and C7—C8—C9—C10—C11—C12 is 64.32 (7)° (Fig. 1).