In the title compound, the dihedral angle between the planes of the bipyridine and carbazole moieties connected by an O atom is 68.45 (3)°. The bipyridine ring system, with two methoxy substituents, is approximately planar. The pyridine ring in the pyridyl-substituted carbazole fragment is tilted by 56.65 (4)° with respect to the mean plane of the carbazole moiety. The title compound exhibits a high energy gap and triplet energy.
Supporting information
CCDC reference: 1957451
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.084
- Data-to-parameter ratio = 15.8
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level C
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage 82 %
Alert level G
PLAT128_ALERT_4_G Alternate Setting for Input Space Group Ia Ic Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 14 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
3 ALERT level G = General information/check it is not something unexpected
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
2 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).
2-[(2',6'-Dimethoxy-2,3'-bipyridin-6-yl)oxy]-9-(pyridin-2-yl)-9
H-carbazole
top
Crystal data top
C29H22N4O3 | F(000) = 992 |
Mr = 474.50 | Dx = 1.385 Mg m−3 |
Monoclinic, Ia | Mo Kα radiation, λ = 0.71073 Å |
a = 9.6979 (1) Å | Cell parameters from 6053 reflections |
b = 23.6702 (3) Å | θ = 2.2–28.3° |
c = 9.9229 (2) Å | µ = 0.09 mm−1 |
β = 92.9125 (5)° | T = 173 K |
V = 2274.87 (6) Å3 | Block, colourless |
Z = 4 | 0.53 × 0.46 × 0.12 mm |
Data collection top
Bruker APEXII CCD diffractometer | 4943 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.020 |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | θmax = 28.4°, θmin = 1.7° |
Tmin = 0.710, Tmax = 0.746 | h = −12→12 |
10918 measured reflections | k = −31→31 |
5179 independent reflections | l = −13→12 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.084 | w = 1/[σ2(Fo2) + (0.0404P)2 + 0.7038P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
5179 reflections | Δρmax = 0.21 e Å−3 |
328 parameters | Δρmin = −0.19 e Å−3 |
2 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0062 (6) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.16676 (16) | 0.24337 (6) | 0.28067 (15) | 0.0285 (3) | |
O2 | −0.27313 (17) | 0.33138 (6) | 0.70330 (18) | 0.0382 (4) | |
O3 | −0.43670 (17) | 0.15756 (6) | 0.82051 (17) | 0.0358 (4) | |
N1 | 0.3339 (2) | 0.06572 (7) | 0.02064 (19) | 0.0287 (4) | |
N2 | 0.30895 (18) | 0.04679 (7) | 0.24867 (18) | 0.0270 (4) | |
N3 | −0.00057 (17) | 0.25161 (7) | 0.43700 (18) | 0.0244 (3) | |
N4 | −0.35398 (18) | 0.24417 (7) | 0.75714 (19) | 0.0273 (4) | |
C1 | 0.3152 (3) | 0.05001 (10) | −0.1083 (2) | 0.0344 (5) | |
H1 | 0.3516 | 0.0737 | −0.1752 | 0.041* | |
C2 | 0.2465 (3) | 0.00167 (10) | −0.1504 (2) | 0.0360 (5) | |
H2 | 0.2399 | −0.0086 | −0.2431 | 0.043* | |
C3 | 0.1874 (3) | −0.03137 (10) | −0.0545 (3) | 0.0379 (5) | |
H3 | 0.1378 | −0.0646 | −0.0801 | 0.045* | |
C4 | 0.2016 (3) | −0.01536 (9) | 0.0794 (2) | 0.0353 (5) | |
H4 | 0.1594 | −0.0365 | 0.1475 | 0.042* | |
C5 | 0.2793 (2) | 0.03247 (8) | 0.1115 (2) | 0.0246 (4) | |
C6 | 0.3774 (2) | 0.01129 (8) | 0.3428 (2) | 0.0261 (4) | |
C7 | 0.4216 (2) | −0.04424 (9) | 0.3285 (2) | 0.0305 (4) | |
H7 | 0.4050 | −0.0642 | 0.2462 | 0.037* | |
C8 | 0.4904 (2) | −0.06934 (9) | 0.4381 (2) | 0.0331 (5) | |
H8 | 0.5208 | −0.1073 | 0.4311 | 0.040* | |
C9 | 0.5164 (3) | −0.04006 (10) | 0.5592 (2) | 0.0356 (5) | |
H9 | 0.5633 | −0.0584 | 0.6333 | 0.043* | |
C10 | 0.4742 (2) | 0.01540 (9) | 0.5717 (2) | 0.0319 (5) | |
H10 | 0.4937 | 0.0355 | 0.6534 | 0.038* | |
C11 | 0.4030 (2) | 0.04161 (8) | 0.4635 (2) | 0.0253 (4) | |
C12 | 0.3469 (2) | 0.09767 (8) | 0.44159 (19) | 0.0231 (4) | |
C13 | 0.3371 (2) | 0.14504 (8) | 0.5239 (2) | 0.0259 (4) | |
H13 | 0.3741 | 0.1443 | 0.6144 | 0.031* | |
C14 | 0.2730 (2) | 0.19313 (8) | 0.4724 (2) | 0.0263 (4) | |
H14 | 0.2648 | 0.2256 | 0.5277 | 0.032* | |
C15 | 0.2203 (2) | 0.19380 (8) | 0.3386 (2) | 0.0243 (4) | |
C16 | 0.2283 (2) | 0.14802 (8) | 0.2536 (2) | 0.0240 (4) | |
H16 | 0.1920 | 0.1493 | 0.1629 | 0.029* | |
C17 | 0.2923 (2) | 0.09974 (8) | 0.3073 (2) | 0.0232 (4) | |
C18 | 0.0820 (2) | 0.27662 (8) | 0.3548 (2) | 0.0239 (4) | |
C19 | 0.0883 (2) | 0.33456 (9) | 0.3325 (2) | 0.0309 (5) | |
H19 | 0.1491 | 0.3506 | 0.2708 | 0.037* | |
C20 | 0.0015 (2) | 0.36732 (9) | 0.4049 (2) | 0.0347 (5) | |
H20 | 0.0019 | 0.4072 | 0.3941 | 0.042* | |
C21 | −0.0865 (2) | 0.34265 (9) | 0.4935 (2) | 0.0299 (5) | |
H21 | −0.1461 | 0.3653 | 0.5440 | 0.036* | |
C22 | −0.0865 (2) | 0.28402 (8) | 0.5075 (2) | 0.0238 (4) | |
C23 | −0.1789 (2) | 0.25192 (8) | 0.5941 (2) | 0.0251 (4) | |
C24 | −0.2697 (2) | 0.27479 (8) | 0.6851 (2) | 0.0261 (4) | |
C25 | −0.3517 (2) | 0.18857 (9) | 0.7446 (2) | 0.0301 (4) | |
C26 | −0.2677 (3) | 0.16054 (10) | 0.6591 (3) | 0.0431 (6) | |
H26 | −0.2689 | 0.1205 | 0.6519 | 0.052* | |
C27 | −0.1815 (3) | 0.19309 (9) | 0.5844 (3) | 0.0374 (5) | |
H27 | −0.1222 | 0.1749 | 0.5245 | 0.045* | |
C28 | −0.3786 (3) | 0.35291 (10) | 0.7870 (3) | 0.0458 (6) | |
H28A | −0.3613 | 0.3930 | 0.8061 | 0.069* | |
H28B | −0.3770 | 0.3317 | 0.8719 | 0.069* | |
H28C | −0.4693 | 0.3486 | 0.7398 | 0.069* | |
C29 | −0.5206 (3) | 0.18868 (10) | 0.9090 (3) | 0.0366 (5) | |
H29A | −0.5724 | 0.1623 | 0.9634 | 0.055* | |
H29B | −0.5854 | 0.2125 | 0.8555 | 0.055* | |
H29C | −0.4616 | 0.2125 | 0.9686 | 0.055* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0366 (8) | 0.0230 (7) | 0.0266 (7) | 0.0077 (6) | 0.0087 (6) | 0.0039 (6) |
O2 | 0.0429 (9) | 0.0230 (7) | 0.0510 (10) | −0.0008 (6) | 0.0243 (8) | −0.0039 (7) |
O3 | 0.0361 (8) | 0.0275 (8) | 0.0446 (10) | −0.0009 (6) | 0.0100 (8) | 0.0102 (7) |
N1 | 0.0347 (9) | 0.0247 (8) | 0.0272 (9) | −0.0012 (7) | 0.0062 (7) | −0.0023 (7) |
N2 | 0.0367 (10) | 0.0195 (8) | 0.0249 (9) | 0.0020 (7) | 0.0032 (7) | −0.0003 (6) |
N3 | 0.0248 (8) | 0.0212 (8) | 0.0275 (8) | 0.0015 (6) | 0.0032 (7) | 0.0005 (6) |
N4 | 0.0247 (9) | 0.0268 (8) | 0.0306 (9) | 0.0009 (7) | 0.0032 (7) | 0.0034 (7) |
C1 | 0.0435 (13) | 0.0330 (11) | 0.0272 (11) | 0.0016 (10) | 0.0085 (9) | −0.0003 (9) |
C2 | 0.0410 (13) | 0.0362 (12) | 0.0303 (11) | 0.0063 (10) | −0.0024 (10) | −0.0106 (9) |
C3 | 0.0409 (13) | 0.0272 (11) | 0.0448 (14) | −0.0027 (9) | −0.0062 (11) | −0.0101 (9) |
C4 | 0.0420 (13) | 0.0277 (11) | 0.0364 (12) | −0.0074 (9) | 0.0034 (10) | −0.0005 (9) |
C5 | 0.0278 (10) | 0.0206 (9) | 0.0254 (10) | 0.0023 (7) | 0.0025 (8) | −0.0029 (7) |
C6 | 0.0282 (10) | 0.0245 (9) | 0.0262 (10) | 0.0008 (8) | 0.0072 (8) | 0.0032 (7) |
C7 | 0.0367 (11) | 0.0240 (9) | 0.0314 (11) | 0.0010 (8) | 0.0094 (9) | −0.0002 (8) |
C8 | 0.0342 (11) | 0.0248 (10) | 0.0413 (12) | 0.0050 (8) | 0.0116 (9) | 0.0054 (9) |
C9 | 0.0386 (12) | 0.0349 (11) | 0.0337 (12) | 0.0095 (9) | 0.0047 (10) | 0.0104 (9) |
C10 | 0.0346 (11) | 0.0351 (11) | 0.0265 (10) | 0.0070 (9) | 0.0055 (9) | 0.0045 (8) |
C11 | 0.0247 (10) | 0.0254 (9) | 0.0264 (10) | 0.0022 (7) | 0.0078 (8) | 0.0023 (8) |
C12 | 0.0227 (9) | 0.0248 (9) | 0.0222 (9) | 0.0009 (7) | 0.0048 (7) | 0.0019 (7) |
C13 | 0.0276 (9) | 0.0288 (10) | 0.0215 (9) | 0.0012 (8) | 0.0034 (7) | −0.0012 (8) |
C14 | 0.0291 (10) | 0.0236 (9) | 0.0268 (10) | 0.0007 (8) | 0.0064 (8) | −0.0039 (8) |
C15 | 0.0238 (9) | 0.0217 (9) | 0.0283 (10) | 0.0009 (7) | 0.0088 (8) | 0.0019 (7) |
C16 | 0.0249 (9) | 0.0243 (9) | 0.0231 (9) | −0.0010 (7) | 0.0043 (7) | 0.0006 (7) |
C17 | 0.0248 (9) | 0.0220 (9) | 0.0233 (9) | −0.0024 (7) | 0.0058 (8) | −0.0015 (7) |
C18 | 0.0256 (9) | 0.0227 (9) | 0.0235 (9) | 0.0039 (8) | 0.0016 (8) | −0.0004 (7) |
C19 | 0.0330 (11) | 0.0242 (10) | 0.0364 (12) | 0.0018 (8) | 0.0099 (9) | 0.0067 (8) |
C20 | 0.0398 (12) | 0.0203 (9) | 0.0448 (13) | 0.0048 (9) | 0.0109 (10) | 0.0036 (9) |
C21 | 0.0297 (10) | 0.0243 (10) | 0.0364 (12) | 0.0059 (8) | 0.0096 (9) | −0.0003 (8) |
C22 | 0.0223 (9) | 0.0221 (9) | 0.0269 (10) | 0.0016 (7) | −0.0002 (8) | 0.0006 (7) |
C23 | 0.0226 (9) | 0.0228 (9) | 0.0300 (10) | 0.0025 (7) | 0.0018 (8) | 0.0030 (8) |
C24 | 0.0246 (9) | 0.0242 (9) | 0.0294 (10) | 0.0011 (7) | 0.0014 (8) | 0.0016 (8) |
C25 | 0.0270 (10) | 0.0275 (10) | 0.0359 (11) | −0.0003 (8) | 0.0025 (9) | 0.0070 (9) |
C26 | 0.0481 (15) | 0.0218 (10) | 0.0613 (17) | 0.0015 (10) | 0.0208 (13) | 0.0050 (10) |
C27 | 0.0407 (12) | 0.0241 (10) | 0.0489 (14) | 0.0037 (9) | 0.0182 (11) | 0.0004 (9) |
C28 | 0.0540 (15) | 0.0298 (11) | 0.0565 (16) | 0.0028 (11) | 0.0298 (13) | −0.0055 (11) |
C29 | 0.0359 (12) | 0.0377 (12) | 0.0370 (12) | −0.0085 (10) | 0.0090 (10) | 0.0034 (10) |
Geometric parameters (Å, º) top
O1—C18 | 1.378 (2) | C10—H10 | 0.9500 |
O1—C15 | 1.395 (2) | C11—C12 | 1.446 (3) |
O2—C24 | 1.352 (2) | C12—C13 | 1.393 (3) |
O2—C28 | 1.443 (3) | C12—C17 | 1.409 (3) |
O3—C25 | 1.360 (3) | C13—C14 | 1.383 (3) |
O3—C29 | 1.431 (3) | C13—H13 | 0.9500 |
N1—C5 | 1.327 (3) | C14—C15 | 1.398 (3) |
N1—C1 | 1.335 (3) | C14—H14 | 0.9500 |
N2—C17 | 1.395 (2) | C15—C16 | 1.378 (3) |
N2—C6 | 1.399 (3) | C16—C17 | 1.393 (3) |
N2—C5 | 1.417 (3) | C16—H16 | 0.9500 |
N3—C18 | 1.312 (3) | C18—C19 | 1.391 (3) |
N3—C22 | 1.353 (3) | C19—C20 | 1.373 (3) |
N4—C25 | 1.322 (3) | C19—H19 | 0.9500 |
N4—C24 | 1.328 (3) | C20—C21 | 1.386 (3) |
C1—C2 | 1.379 (3) | C20—H20 | 0.9500 |
C1—H1 | 0.9500 | C21—C22 | 1.395 (3) |
C2—C3 | 1.379 (4) | C21—H21 | 0.9500 |
C2—H2 | 0.9500 | C22—C23 | 1.482 (3) |
C3—C4 | 1.382 (3) | C23—C27 | 1.396 (3) |
C3—H3 | 0.9500 | C23—C24 | 1.402 (3) |
C4—C5 | 1.388 (3) | C25—C26 | 1.377 (3) |
C4—H4 | 0.9500 | C26—C27 | 1.380 (3) |
C6—C7 | 1.392 (3) | C26—H26 | 0.9500 |
C6—C11 | 1.407 (3) | C27—H27 | 0.9500 |
C7—C8 | 1.380 (3) | C28—H28A | 0.9800 |
C7—H7 | 0.9500 | C28—H28B | 0.9800 |
C8—C9 | 1.399 (3) | C28—H28C | 0.9800 |
C8—H8 | 0.9500 | C29—H29A | 0.9800 |
C9—C10 | 1.382 (3) | C29—H29B | 0.9800 |
C9—H9 | 0.9500 | C29—H29C | 0.9800 |
C10—C11 | 1.393 (3) | | |
| | | |
C18—O1—C15 | 118.70 (15) | C16—C15—O1 | 116.16 (18) |
C24—O2—C28 | 116.72 (17) | C16—C15—C14 | 122.88 (18) |
C25—O3—C29 | 116.20 (17) | O1—C15—C14 | 120.73 (17) |
C5—N1—C1 | 116.50 (19) | C15—C16—C17 | 116.67 (18) |
C17—N2—C6 | 108.79 (16) | C15—C16—H16 | 121.7 |
C17—N2—C5 | 126.41 (16) | C17—C16—H16 | 121.7 |
C6—N2—C5 | 124.30 (16) | C16—C17—N2 | 129.49 (18) |
C18—N3—C22 | 118.47 (17) | C16—C17—C12 | 121.93 (18) |
C25—N4—C24 | 118.63 (19) | N2—C17—C12 | 108.51 (16) |
N1—C1—C2 | 124.2 (2) | N3—C18—O1 | 118.27 (17) |
N1—C1—H1 | 117.9 | N3—C18—C19 | 125.21 (19) |
C2—C1—H1 | 117.9 | O1—C18—C19 | 116.49 (19) |
C3—C2—C1 | 118.2 (2) | C20—C19—C18 | 116.1 (2) |
C3—C2—H2 | 120.9 | C20—C19—H19 | 121.9 |
C1—C2—H2 | 120.9 | C18—C19—H19 | 121.9 |
C2—C3—C4 | 118.9 (2) | C19—C20—C21 | 120.5 (2) |
C2—C3—H3 | 120.5 | C19—C20—H20 | 119.7 |
C4—C3—H3 | 120.5 | C21—C20—H20 | 119.7 |
C3—C4—C5 | 118.1 (2) | C20—C21—C22 | 119.04 (19) |
C3—C4—H4 | 120.9 | C20—C21—H21 | 120.5 |
C5—C4—H4 | 120.9 | C22—C21—H21 | 120.5 |
N1—C5—C4 | 123.9 (2) | N3—C22—C21 | 120.63 (19) |
N1—C5—N2 | 116.24 (18) | N3—C22—C23 | 114.54 (16) |
C4—C5—N2 | 119.80 (19) | C21—C22—C23 | 124.80 (18) |
C7—C6—N2 | 129.6 (2) | C27—C23—C24 | 114.82 (19) |
C7—C6—C11 | 121.8 (2) | C27—C23—C22 | 118.74 (19) |
N2—C6—C11 | 108.61 (17) | C24—C23—C22 | 126.41 (18) |
C8—C7—C6 | 117.7 (2) | N4—C24—O2 | 116.67 (18) |
C8—C7—H7 | 121.1 | N4—C24—C23 | 124.05 (18) |
C6—C7—H7 | 121.1 | O2—C24—C23 | 119.27 (18) |
C7—C8—C9 | 121.5 (2) | N4—C25—O3 | 118.2 (2) |
C7—C8—H8 | 119.3 | N4—C25—C26 | 123.4 (2) |
C9—C8—H8 | 119.3 | O3—C25—C26 | 118.41 (19) |
C10—C9—C8 | 120.4 (2) | C25—C26—C27 | 117.1 (2) |
C10—C9—H9 | 119.8 | C25—C26—H26 | 121.4 |
C8—C9—H9 | 119.8 | C27—C26—H26 | 121.4 |
C9—C10—C11 | 119.4 (2) | C26—C27—C23 | 121.9 (2) |
C9—C10—H10 | 120.3 | C26—C27—H27 | 119.0 |
C11—C10—H10 | 120.3 | C23—C27—H27 | 119.0 |
C10—C11—C6 | 119.22 (19) | O2—C28—H28A | 109.5 |
C10—C11—C12 | 133.8 (2) | O2—C28—H28B | 109.5 |
C6—C11—C12 | 106.95 (17) | H28A—C28—H28B | 109.5 |
C13—C12—C17 | 119.52 (18) | O2—C28—H28C | 109.5 |
C13—C12—C11 | 133.37 (18) | H28A—C28—H28C | 109.5 |
C17—C12—C11 | 107.10 (17) | H28B—C28—H28C | 109.5 |
C14—C13—C12 | 119.24 (19) | O3—C29—H29A | 109.5 |
C14—C13—H13 | 120.4 | O3—C29—H29B | 109.5 |
C12—C13—H13 | 120.4 | H29A—C29—H29B | 109.5 |
C13—C14—C15 | 119.76 (18) | O3—C29—H29C | 109.5 |
C13—C14—H14 | 120.1 | H29A—C29—H29C | 109.5 |
C15—C14—H14 | 120.1 | H29B—C29—H29C | 109.5 |
| | | |
C5—N1—C1—C2 | −1.4 (3) | C6—N2—C17—C16 | −178.7 (2) |
N1—C1—C2—C3 | 3.2 (4) | C5—N2—C17—C16 | 9.2 (3) |
C1—C2—C3—C4 | −1.1 (4) | C6—N2—C17—C12 | −1.7 (2) |
C2—C3—C4—C5 | −2.3 (4) | C5—N2—C17—C12 | −173.88 (18) |
C1—N1—C5—C4 | −2.4 (3) | C13—C12—C17—C16 | 0.0 (3) |
C1—N1—C5—N2 | 175.06 (19) | C11—C12—C17—C16 | 179.17 (18) |
C3—C4—C5—N1 | 4.3 (3) | C13—C12—C17—N2 | −177.21 (18) |
C3—C4—C5—N2 | −173.1 (2) | C11—C12—C17—N2 | 2.0 (2) |
C17—N2—C5—N1 | 51.1 (3) | C22—N3—C18—O1 | −178.41 (17) |
C6—N2—C5—N1 | −119.9 (2) | C22—N3—C18—C19 | −0.6 (3) |
C17—N2—C5—C4 | −131.3 (2) | C15—O1—C18—N3 | −34.5 (3) |
C6—N2—C5—C4 | 57.7 (3) | C15—O1—C18—C19 | 147.49 (19) |
C17—N2—C6—C7 | −177.0 (2) | N3—C18—C19—C20 | 0.9 (3) |
C5—N2—C6—C7 | −4.6 (3) | O1—C18—C19—C20 | 178.79 (19) |
C17—N2—C6—C11 | 0.8 (2) | C18—C19—C20—C21 | −0.4 (4) |
C5—N2—C6—C11 | 173.16 (18) | C19—C20—C21—C22 | −0.4 (4) |
N2—C6—C7—C8 | 178.5 (2) | C18—N3—C22—C21 | −0.3 (3) |
C11—C6—C7—C8 | 1.0 (3) | C18—N3—C22—C23 | 178.03 (17) |
C6—C7—C8—C9 | −0.6 (3) | C20—C21—C22—N3 | 0.8 (3) |
C7—C8—C9—C10 | −0.5 (4) | C20—C21—C22—C23 | −177.4 (2) |
C8—C9—C10—C11 | 1.3 (4) | N3—C22—C23—C27 | −7.2 (3) |
C9—C10—C11—C6 | −1.0 (3) | C21—C22—C23—C27 | 171.1 (2) |
C9—C10—C11—C12 | −179.1 (2) | N3—C22—C23—C24 | 174.66 (18) |
C7—C6—C11—C10 | −0.2 (3) | C21—C22—C23—C24 | −7.0 (3) |
N2—C6—C11—C10 | −178.16 (18) | C25—N4—C24—O2 | −178.53 (19) |
C7—C6—C11—C12 | 178.39 (19) | C25—N4—C24—C23 | 1.0 (3) |
N2—C6—C11—C12 | 0.4 (2) | C28—O2—C24—N4 | −6.9 (3) |
C10—C11—C12—C13 | −4.2 (4) | C28—O2—C24—C23 | 173.6 (2) |
C6—C11—C12—C13 | 177.6 (2) | C27—C23—C24—N4 | −0.6 (3) |
C10—C11—C12—C17 | 176.8 (2) | C22—C23—C24—N4 | 177.60 (19) |
C6—C11—C12—C17 | −1.4 (2) | C27—C23—C24—O2 | 178.9 (2) |
C17—C12—C13—C14 | 0.4 (3) | C22—C23—C24—O2 | −2.9 (3) |
C11—C12—C13—C14 | −178.5 (2) | C24—N4—C25—O3 | 178.91 (18) |
C12—C13—C14—C15 | −0.6 (3) | C24—N4—C25—C26 | −1.0 (4) |
C18—O1—C15—C16 | 141.73 (19) | C29—O3—C25—N4 | −0.6 (3) |
C18—O1—C15—C14 | −43.6 (3) | C29—O3—C25—C26 | 179.2 (2) |
C13—C14—C15—C16 | 0.3 (3) | N4—C25—C26—C27 | 0.5 (4) |
C13—C14—C15—O1 | −174.02 (18) | O3—C25—C26—C27 | −179.4 (2) |
O1—C15—C16—C17 | 174.71 (16) | C25—C26—C27—C23 | −0.1 (4) |
C14—C15—C16—C17 | 0.1 (3) | C24—C23—C27—C26 | 0.1 (4) |
C15—C16—C17—N2 | 176.29 (19) | C22—C23—C27—C26 | −178.2 (2) |
C15—C16—C17—C12 | −0.3 (3) | | |
Hydrogen-bond geometry (Å, º) topCg1 is the centroid of the C12–C17 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O3i | 0.95 | 2.50 | 3.429 (3) | 165 |
C21—H21···O2 | 0.95 | 2.20 | 2.839 (3) | 123 |
C27—H27···N3 | 0.95 | 2.35 | 2.720 (3) | 102 |
C29—H29A···N1ii | 0.98 | 2.54 | 3.442 (3) | 154 |
C8—H8···Cg1iii | 0.95 | 2.76 | 3.426 (2) | 128 |
C28—H28C···Cg1iv | 0.98 | 2.89 | 3.485 (3) | 120 |
Symmetry codes: (i) x+1/2, −y, z−1; (ii) x−1, y, z+1; (iii) x+1/2, −y, z; (iv) x−1, −y+1/2, z+1/2. |