Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604390X/lh2210sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680604390X/lh2210Isup2.hkl |
CCDC reference: 627997
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
C16H13N3 | F(000) = 1040 |
Mr = 247.29 | Dx = 1.331 Mg m−3 |
Monoclinic, P21/c | Melting point = 407–408 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 18.8775 (6) Å | Cell parameters from 4351 reflections |
b = 7.3316 (2) Å | θ = 1.3–25.0° |
c = 21.3634 (7) Å | µ = 0.08 mm−1 |
β = 123.413 (2)° | T = 100 K |
V = 2468.06 (14) Å3 | Block, colorless |
Z = 8 | 0.15 × 0.11 × 0.07 mm |
Bruker SMART APEX2 CCD area-detector diffractometer | 4351 independent reflections |
Radiation source: fine-focus sealed tube | 2205 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.128 |
Detector resolution: 8.33 pixels mm-1 | θmax = 25.0°, θmin = 1.3° |
ω scans | h = −22→22 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −8→8 |
Tmin = 0.989, Tmax = 0.994 | l = −25→25 |
22973 measured reflections |
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)] = 0.088 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.294 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1711P)2] where P = (Fo2 + 2Fc2)/3 |
4351 reflections | (Δ/σ)max < 0.001 |
359 parameters | Δρmax = 0.78 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
Experimental. IR (KBr): 3475, 3302, 3171, 1628, 1566, 1542, 1364, 763 cm-1. |
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 | ||
N1A | 0.2788 (2) | −0.7130 (5) | −0.4030 (2) | 0.0159 (9) | |
N2A | 0.1968 (3) | −0.7276 (5) | −0.3479 (2) | 0.0172 (9) | |
N3A | 0.1332 (3) | −0.6949 (6) | −0.4749 (2) | 0.0225 (10) | |
C1A | 0.1897 (3) | −0.8169 (6) | −0.2191 (3) | 0.0208 (11) | |
H1AA | 0.1464 | −0.8690 | −0.2637 | 0.025* | |
C2A | 0.1818 (3) | −0.8078 (7) | −0.1594 (3) | 0.0241 (12) | |
H2AA | 0.1334 | −0.8546 | −0.1638 | 0.029* | |
C3A | 0.2452 (3) | −0.7293 (7) | −0.0917 (3) | 0.0242 (12) | |
H3AA | 0.2389 | −0.7204 | −0.0516 | 0.029* | |
C4A | 0.3174 (3) | −0.6654 (7) | −0.0855 (3) | 0.0234 (12) | |
H4AA | 0.3608 | −0.6159 | −0.0403 | 0.028* | |
C5A | 0.3262 (3) | −0.6737 (6) | −0.1459 (3) | 0.0190 (11) | |
H5AA | 0.3752 | −0.6289 | −0.1409 | 0.023* | |
C6A | 0.2616 (3) | −0.7493 (6) | −0.2143 (3) | 0.0186 (11) | |
C7A | 0.2688 (3) | −0.7475 (6) | −0.2802 (3) | 0.0182 (11) | |
C8A | 0.3475 (3) | −0.7622 (6) | −0.2715 (3) | 0.0196 (11) | |
H8AA | 0.3966 | −0.7857 | −0.2249 | 0.024* | |
C9A | 0.3502 (3) | −0.7406 (6) | −0.3351 (3) | 0.0172 (11) | |
C10A | 0.4312 (3) | −0.7388 (6) | −0.3298 (2) | 0.0160 (11) | |
C11A | 0.5050 (3) | −0.8158 (6) | −0.2692 (3) | 0.0185 (11) | |
H11A | 0.5027 | −0.8740 | −0.2317 | 0.022* | |
C12A | 0.5814 (3) | −0.8074 (6) | −0.2636 (3) | 0.0222 (12) | |
H12A | 0.6298 | −0.8580 | −0.2223 | 0.027* | |
C13A | 0.5860 (3) | −0.7237 (7) | −0.3196 (3) | 0.0239 (12) | |
H13A | 0.6371 | −0.7192 | −0.3165 | 0.029* | |
C14A | 0.5130 (3) | −0.6467 (7) | −0.3805 (3) | 0.0228 (12) | |
H14A | 0.5158 | −0.5893 | −0.4179 | 0.027* | |
C15A | 0.4366 (3) | −0.6540 (6) | −0.3863 (3) | 0.0197 (11) | |
H15A | 0.3883 | −0.6027 | −0.4277 | 0.024* | |
C16A | 0.2062 (3) | −0.7136 (6) | −0.4059 (3) | 0.0173 (11) | |
N1B | 0.1241 (3) | −0.2879 (5) | −0.5519 (2) | 0.0200 (10) | |
N2B | 0.0423 (2) | −0.2672 (5) | −0.4965 (2) | 0.0168 (9) | |
N3B | −0.0180 (3) | −0.3430 (6) | −0.6204 (3) | 0.0224 (11) | |
C1B | 0.0336 (3) | −0.1414 (6) | −0.3728 (3) | 0.0206 (12) | |
H1BA | −0.0064 | −0.0844 | −0.4176 | 0.025* | |
C2B | 0.0224 (3) | −0.1466 (7) | −0.3134 (3) | 0.0234 (12) | |
H2BA | −0.0253 | −0.0934 | −0.3187 | 0.028* | |
C3B | 0.0821 (3) | −0.2306 (7) | −0.2469 (3) | 0.0246 (12) | |
H3BA | 0.0738 | −0.2355 | −0.2079 | 0.029* | |
C4B | 0.1558 (3) | −0.3091 (6) | −0.2376 (3) | 0.0219 (12) | |
H4BA | 0.1965 | −0.3646 | −0.1926 | 0.026* | |
C5B | 0.1658 (3) | −0.3014 (6) | −0.2967 (3) | 0.0201 (11) | |
H5BA | 0.2145 | −0.3508 | −0.2907 | 0.024* | |
C6B | 0.1060 (3) | −0.2229 (6) | −0.3644 (3) | 0.0167 (11) | |
C7B | 0.1138 (3) | −0.2318 (6) | −0.4302 (3) | 0.0156 (10) | |
C8B | 0.1919 (3) | −0.2163 (6) | −0.4220 (3) | 0.0191 (11) | |
H8BA | 0.2409 | −0.1872 | −0.3760 | 0.023* | |
C9B | 0.1941 (3) | −0.2459 (6) | −0.4853 (3) | 0.0167 (11) | |
C10B | 0.2750 (3) | −0.2381 (6) | −0.4824 (3) | 0.0185 (11) | |
C11B | 0.3488 (3) | −0.1546 (6) | −0.4233 (3) | 0.0199 (11) | |
H11B | 0.3481 | −0.0987 | −0.3845 | 0.024* | |
C12B | 0.4228 (3) | −0.1553 (7) | −0.4226 (3) | 0.0201 (11) | |
H12B | 0.4713 | −0.0999 | −0.3831 | 0.024* | |
C13B | 0.4254 (3) | −0.2359 (7) | −0.4790 (3) | 0.0252 (12) | |
H13B | 0.4753 | −0.2351 | −0.4779 | 0.030* | |
C14B | 0.3529 (3) | −0.3194 (7) | −0.5382 (3) | 0.0263 (13) | |
H14B | 0.3544 | −0.3752 | −0.5765 | 0.032* | |
C15B | 0.2784 (3) | −0.3190 (7) | −0.5399 (3) | 0.0213 (12) | |
H15B | 0.2299 | −0.3734 | −0.5800 | 0.026* | |
C16B | 0.0502 (3) | −0.2966 (6) | −0.5553 (3) | 0.0183 (11) | |
H1NA | 0.079 (4) | −0.715 (7) | −0.486 (3) | 0.038 (17)* | |
H2NA | 0.136 (4) | −0.668 (8) | −0.514 (4) | 0.05 (2)* | |
H1NB | −0.060 (3) | −0.324 (7) | −0.626 (3) | 0.011 (15)* | |
H2NB | −0.012 (3) | −0.358 (6) | −0.655 (3) | 0.016 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.015 (2) | 0.015 (2) | 0.011 (2) | −0.0005 (16) | 0.0029 (18) | 0.0000 (16) |
N2A | 0.020 (2) | 0.016 (2) | 0.011 (2) | −0.0027 (17) | 0.0051 (18) | 0.0003 (16) |
N3A | 0.009 (2) | 0.040 (3) | 0.014 (2) | 0.0022 (19) | 0.004 (2) | 0.0014 (19) |
C1A | 0.014 (3) | 0.023 (3) | 0.018 (3) | −0.001 (2) | 0.005 (2) | 0.001 (2) |
C2A | 0.019 (3) | 0.027 (3) | 0.028 (3) | 0.001 (2) | 0.014 (3) | 0.005 (2) |
C3A | 0.025 (3) | 0.033 (3) | 0.021 (3) | 0.005 (2) | 0.016 (3) | 0.008 (2) |
C4A | 0.022 (3) | 0.026 (3) | 0.018 (3) | 0.000 (2) | 0.009 (2) | 0.001 (2) |
C5A | 0.018 (3) | 0.024 (3) | 0.016 (3) | −0.005 (2) | 0.010 (2) | 0.000 (2) |
C6A | 0.021 (3) | 0.020 (3) | 0.015 (3) | 0.002 (2) | 0.011 (2) | 0.002 (2) |
C7A | 0.018 (3) | 0.016 (3) | 0.021 (3) | −0.004 (2) | 0.011 (2) | −0.001 (2) |
C8A | 0.013 (3) | 0.029 (3) | 0.011 (2) | 0.002 (2) | 0.003 (2) | 0.001 (2) |
C9A | 0.022 (3) | 0.014 (2) | 0.017 (3) | −0.001 (2) | 0.012 (2) | −0.0009 (19) |
C10A | 0.020 (3) | 0.014 (2) | 0.010 (2) | 0.000 (2) | 0.005 (2) | −0.0009 (19) |
C11A | 0.018 (3) | 0.021 (3) | 0.016 (3) | −0.002 (2) | 0.009 (2) | −0.001 (2) |
C12A | 0.018 (3) | 0.019 (3) | 0.012 (3) | −0.001 (2) | −0.003 (2) | 0.004 (2) |
C13A | 0.022 (3) | 0.028 (3) | 0.027 (3) | −0.002 (2) | 0.017 (3) | 0.000 (2) |
C14A | 0.018 (3) | 0.033 (3) | 0.019 (3) | 0.005 (2) | 0.011 (2) | 0.003 (2) |
C15A | 0.018 (3) | 0.022 (3) | 0.016 (3) | −0.001 (2) | 0.007 (2) | −0.001 (2) |
C16A | 0.017 (3) | 0.017 (3) | 0.016 (3) | 0.004 (2) | 0.008 (2) | 0.001 (2) |
N1B | 0.016 (2) | 0.024 (2) | 0.018 (2) | −0.0006 (18) | 0.008 (2) | −0.0004 (17) |
N2B | 0.015 (2) | 0.016 (2) | 0.018 (2) | 0.0041 (16) | 0.0076 (19) | 0.0017 (17) |
N3B | 0.018 (3) | 0.035 (3) | 0.017 (3) | −0.003 (2) | 0.012 (2) | −0.0046 (19) |
C1B | 0.019 (3) | 0.020 (3) | 0.018 (3) | −0.001 (2) | 0.008 (2) | −0.004 (2) |
C2B | 0.016 (3) | 0.035 (3) | 0.025 (3) | −0.003 (2) | 0.015 (2) | −0.009 (2) |
C3B | 0.026 (3) | 0.031 (3) | 0.022 (3) | −0.003 (2) | 0.017 (3) | −0.003 (2) |
C4B | 0.032 (3) | 0.018 (3) | 0.016 (3) | −0.007 (2) | 0.014 (3) | −0.003 (2) |
C5B | 0.018 (3) | 0.021 (3) | 0.020 (3) | 0.000 (2) | 0.010 (2) | −0.002 (2) |
C6B | 0.018 (3) | 0.017 (2) | 0.018 (3) | −0.008 (2) | 0.012 (2) | −0.009 (2) |
C7B | 0.015 (3) | 0.015 (2) | 0.015 (2) | 0.0019 (19) | 0.008 (2) | 0.0001 (19) |
C8B | 0.011 (3) | 0.023 (3) | 0.016 (3) | −0.001 (2) | 0.003 (2) | −0.003 (2) |
C9B | 0.013 (3) | 0.017 (2) | 0.014 (2) | −0.0002 (19) | 0.004 (2) | −0.0014 (19) |
C10B | 0.015 (3) | 0.020 (3) | 0.018 (3) | 0.005 (2) | 0.007 (2) | 0.002 (2) |
C11B | 0.018 (3) | 0.026 (3) | 0.012 (2) | 0.004 (2) | 0.006 (2) | −0.003 (2) |
C12B | 0.008 (3) | 0.035 (3) | 0.014 (3) | 0.006 (2) | 0.004 (2) | 0.006 (2) |
C13B | 0.015 (3) | 0.035 (3) | 0.025 (3) | 0.001 (2) | 0.011 (2) | 0.001 (2) |
C14B | 0.024 (3) | 0.023 (3) | 0.028 (3) | 0.005 (2) | 0.012 (3) | 0.001 (2) |
C15B | 0.019 (3) | 0.026 (3) | 0.019 (3) | 0.000 (2) | 0.011 (2) | 0.002 (2) |
C16B | 0.019 (3) | 0.016 (2) | 0.020 (3) | 0.003 (2) | 0.010 (2) | 0.002 (2) |
N1A—C9A | 1.344 (6) | N1B—C9B | 1.340 (6) |
N1A—C16A | 1.338 (6) | N1B—C16B | 1.359 (6) |
N2A—C7A | 1.341 (6) | N2B—C7B | 1.339 (6) |
N2A—C16A | 1.349 (6) | N2B—C16B | 1.359 (6) |
N3A—C16A | 1.362 (6) | N3B—C16B | 1.317 (6) |
N3A—H1NA | 0.93 (6) | N3B—H1NB | 0.75 (5) |
N3A—H2NA | 0.89 (6) | N3B—H2NB | 0.82 (5) |
C1A—C2A | 1.365 (7) | C1B—C2B | 1.398 (6) |
C1A—C6A | 1.395 (7) | C1B—C6B | 1.409 (7) |
C1A—H1AA | 0.9300 | C1B—H1BA | 0.9300 |
C2A—C3A | 1.396 (7) | C2B—C3B | 1.379 (7) |
C2A—H2AA | 0.9300 | C2B—H2BA | 0.9300 |
C3A—C4A | 1.376 (7) | C3B—C4B | 1.414 (7) |
C3A—H3AA | 0.9300 | C3B—H3BA | 0.9300 |
C4A—C5A | 1.390 (7) | C4B—C5B | 1.377 (7) |
C4A—H4AA | 0.9300 | C4B—H4BA | 0.9300 |
C5A—C6A | 1.403 (6) | C5B—C6B | 1.379 (7) |
C5A—H5AA | 0.9300 | C5B—H5BA | 0.9300 |
C6A—C7A | 1.487 (7) | C6B—C7B | 1.493 (6) |
C7A—C8A | 1.396 (7) | C7B—C8B | 1.390 (7) |
C8A—C9A | 1.397 (6) | C8B—C9B | 1.393 (7) |
C8A—H8AA | 0.9300 | C8B—H8BA | 0.9300 |
C9A—C10A | 1.470 (7) | C9B—C10B | 1.494 (7) |
C10A—C11A | 1.397 (6) | C10B—C15B | 1.398 (7) |
C10A—C15A | 1.409 (6) | C10B—C11B | 1.404 (7) |
C11A—C12A | 1.380 (7) | C11B—C12B | 1.388 (7) |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C13A | 1.390 (7) | C12B—C13B | 1.368 (7) |
C12A—H12A | 0.9300 | C12B—H12B | 0.9300 |
C13A—C14A | 1.390 (7) | C13B—C14B | 1.393 (7) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.380 (7) | C14B—C15B | 1.387 (7) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—N1A—C9A | 116.3 (4) | C9B—N1B—C16B | 116.8 (4) |
C7A—N2A—C16A | 115.5 (4) | C7B—N2B—C16B | 116.7 (4) |
C16A—N3A—H1NA | 125 (3) | C16B—N3B—H1NB | 117 (4) |
C16A—N3A—H2NA | 119 (4) | C16B—N3B—H2NB | 117 (4) |
H1NA—N3A—H2NA | 116 (5) | H1NB—N3B—H2NB | 123 (5) |
C2A—C1A—C6A | 121.1 (5) | C2B—C1B—C6B | 119.6 (5) |
C2A—C1A—H1AA | 119.4 | C2B—C1B—H1BA | 120.2 |
C6A—C1A—H1AA | 119.4 | C6B—C1B—H1BA | 120.2 |
C1A—C2A—C3A | 121.0 (5) | C3B—C2B—C1B | 120.0 (5) |
C1A—C2A—H2AA | 119.5 | C3B—C2B—H2BA | 120.0 |
C3A—C2A—H2AA | 119.5 | C1B—C2B—H2BA | 120.0 |
C4A—C3A—C2A | 118.6 (5) | C2B—C3B—C4B | 120.7 (4) |
C4A—C3A—H3AA | 120.7 | C2B—C3B—H3BA | 119.7 |
C2A—C3A—H3AA | 120.7 | C4B—C3B—H3BA | 119.7 |
C3A—C4A—C5A | 120.9 (5) | C5B—C4B—C3B | 118.3 (5) |
C3A—C4A—H4AA | 119.5 | C5B—C4B—H4BA | 120.8 |
C5A—C4A—H4AA | 119.5 | C3B—C4B—H4BA | 120.8 |
C4A—C5A—C6A | 120.3 (5) | C4B—C5B—C6B | 122.2 (5) |
C4A—C5A—H5AA | 119.9 | C4B—C5B—H5BA | 118.9 |
C6A—C5A—H5AA | 119.9 | C6B—C5B—H5BA | 118.9 |
C1A—C6A—C5A | 118.0 (4) | C5B—C6B—C1B | 119.1 (4) |
C1A—C6A—C7A | 121.8 (4) | C5B—C6B—C7B | 121.4 (4) |
C5A—C6A—C7A | 120.1 (4) | C1B—C6B—C7B | 119.4 (4) |
N2A—C7A—C8A | 121.6 (4) | N2B—C7B—C8B | 122.0 (4) |
N2A—C7A—C6A | 117.0 (4) | N2B—C7B—C6B | 116.1 (4) |
C8A—C7A—C6A | 121.3 (4) | C8B—C7B—C6B | 121.7 (4) |
C7A—C8A—C9A | 117.9 (4) | C7B—C8B—C9B | 117.5 (4) |
C7A—C8A—H8AA | 121.0 | C7B—C8B—H8BA | 121.3 |
C9A—C8A—H8AA | 121.0 | C9B—C8B—H8BA | 121.3 |
N1A—C9A—C8A | 120.9 (5) | N1B—C9B—C8B | 121.9 (4) |
N1A—C9A—C10A | 117.7 (4) | N1B—C9B—C10B | 116.2 (4) |
C8A—C9A—C10A | 121.3 (4) | C8B—C9B—C10B | 121.9 (4) |
C11A—C10A—C15A | 117.9 (4) | C15B—C10B—C11B | 118.2 (5) |
C11A—C10A—C9A | 122.1 (4) | C15B—C10B—C9B | 119.2 (4) |
C15A—C10A—C9A | 120.0 (4) | C11B—C10B—C9B | 122.7 (4) |
C12A—C11A—C10A | 121.5 (4) | C12B—C11B—C10B | 120.2 (4) |
C12A—C11A—H11A | 119.2 | C12B—C11B—H11B | 119.9 |
C10A—C11A—H11A | 119.2 | C10B—C11B—H11B | 119.9 |
C11A—C12A—C13A | 120.2 (5) | C13B—C12B—C11B | 121.1 (5) |
C11A—C12A—H12A | 119.9 | C13B—C12B—H12B | 119.5 |
C13A—C12A—H12A | 119.9 | C11B—C12B—H12B | 119.5 |
C12A—C13A—C14A | 119.0 (5) | C12B—C13B—C14B | 119.7 (5) |
C12A—C13A—H13A | 120.5 | C12B—C13B—H13B | 120.1 |
C14A—C13A—H13A | 120.5 | C14B—C13B—H13B | 120.1 |
C15A—C14A—C13A | 121.2 (5) | C15B—C14B—C13B | 119.9 (5) |
C15A—C14A—H14A | 119.4 | C15B—C14B—H14B | 120.1 |
C13A—C14A—H14A | 119.4 | C13B—C14B—H14B | 120.1 |
C14A—C15A—C10A | 120.3 (5) | C14B—C15B—C10B | 121.0 (5) |
C14A—C15A—H15A | 119.9 | C14B—C15B—H15B | 119.5 |
C10A—C15A—H15A | 119.9 | C10B—C15B—H15B | 119.5 |
N1A—C16A—N2A | 127.5 (4) | N3B—C16B—N1B | 116.5 (5) |
N1A—C16A—N3A | 116.8 (4) | N3B—C16B—N2B | 118.4 (5) |
N2A—C16A—N3A | 115.8 (4) | N1B—C16B—N2B | 125.1 (4) |
C6A—C1A—C2A—C3A | 0.5 (8) | C6B—C1B—C2B—C3B | 0.3 (7) |
C1A—C2A—C3A—C4A | −1.8 (7) | C1B—C2B—C3B—C4B | 1.1 (8) |
C2A—C3A—C4A—C5A | 1.8 (7) | C2B—C3B—C4B—C5B | −0.7 (7) |
C3A—C4A—C5A—C6A | −0.5 (7) | C3B—C4B—C5B—C6B | −1.1 (7) |
C2A—C1A—C6A—C5A | 0.8 (7) | C4B—C5B—C6B—C1B | 2.5 (7) |
C2A—C1A—C6A—C7A | −176.1 (4) | C4B—C5B—C6B—C7B | −174.0 (4) |
C4A—C5A—C6A—C1A | −0.8 (7) | C2B—C1B—C6B—C5B | −2.0 (7) |
C4A—C5A—C6A—C7A | 176.2 (4) | C2B—C1B—C6B—C7B | 174.5 (4) |
C16A—N2A—C7A—C8A | −3.3 (7) | C16B—N2B—C7B—C8B | 3.3 (6) |
C16A—N2A—C7A—C6A | 175.5 (4) | C16B—N2B—C7B—C6B | −172.6 (4) |
C1A—C6A—C7A—N2A | 31.1 (7) | C5B—C6B—C7B—N2B | 137.7 (5) |
C5A—C6A—C7A—N2A | −145.8 (4) | C1B—C6B—C7B—N2B | −38.8 (6) |
C1A—C6A—C7A—C8A | −150.1 (5) | C5B—C6B—C7B—C8B | −38.2 (7) |
C5A—C6A—C7A—C8A | 33.0 (7) | C1B—C6B—C7B—C8B | 145.3 (5) |
N2A—C7A—C8A—C9A | 5.2 (7) | N2B—C7B—C8B—C9B | −2.4 (7) |
C6A—C7A—C8A—C9A | −173.5 (4) | C6B—C7B—C8B—C9B | 173.2 (4) |
C16A—N1A—C9A—C8A | −2.1 (6) | C16B—N1B—C9B—C8B | 1.4 (7) |
C16A—N1A—C9A—C10A | −179.3 (4) | C16B—N1B—C9B—C10B | 179.6 (4) |
C7A—C8A—C9A—N1A | −2.4 (7) | C7B—C8B—C9B—N1B | −0.1 (7) |
C7A—C8A—C9A—C10A | 174.8 (4) | C7B—C8B—C9B—C10B | −178.1 (4) |
N1A—C9A—C10A—C11A | −161.2 (4) | N1B—C9B—C10B—C15B | −16.7 (6) |
C8A—C9A—C10A—C11A | 21.6 (7) | C8B—C9B—C10B—C15B | 161.5 (4) |
N1A—C9A—C10A—C15A | 20.2 (6) | N1B—C9B—C10B—C11B | 164.2 (4) |
C8A—C9A—C10A—C15A | −157.0 (4) | C8B—C9B—C10B—C11B | −17.6 (7) |
C15A—C10A—C11A—C12A | 1.0 (7) | C15B—C10B—C11B—C12B | −0.6 (7) |
C9A—C10A—C11A—C12A | −177.7 (4) | C9B—C10B—C11B—C12B | 178.5 (4) |
C10A—C11A—C12A—C13A | −1.0 (7) | C10B—C11B—C12B—C13B | 0.2 (7) |
C11A—C12A—C13A—C14A | 0.9 (7) | C11B—C12B—C13B—C14B | −0.1 (8) |
C12A—C13A—C14A—C15A | −0.7 (7) | C12B—C13B—C14B—C15B | 0.5 (8) |
C13A—C14A—C15A—C10A | 0.6 (7) | C13B—C14B—C15B—C10B | −0.9 (7) |
C11A—C10A—C15A—C14A | −0.8 (7) | C11B—C10B—C15B—C14B | 1.0 (7) |
C9A—C10A—C15A—C14A | 177.9 (4) | C9B—C10B—C15B—C14B | −178.2 (4) |
C9A—N1A—C16A—N2A | 4.4 (7) | C9B—N1B—C16B—N3B | −178.2 (4) |
C9A—N1A—C16A—N3A | −176.8 (4) | C9B—N1B—C16B—N2B | −0.4 (7) |
C7A—N2A—C16A—N1A | −1.7 (7) | C7B—N2B—C16B—N3B | 175.8 (4) |
C7A—N2A—C16A—N3A | 179.5 (4) | C7B—N2B—C16B—N1B | −1.8 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H1NA···N2Bi | 0.93 (8) | 2.11 (8) | 3.033 (8) | 173 (3) |
N3B—H1NB···N2Ai | 0.75 (7) | 2.35 (7) | 3.099 (9) | 176 (6) |
C15B—H15B···N1B | 0.93 | 2.46 | 2.789 (9) | 101 |
C1A—H1AA···Cg3ii | 0.93 | 2.76 | 3.457 (5) | 132 |
C4A—H4AA···Cg5iii | 0.93 | 2.94 | 3.543 (6) | 124 |
C11A—H11A···Cg4iv | 0.93 | 2.94 | 3.736 (5) | 144 |
C12A—H12A···Cg1iv | 0.93 | 3.16 | 3.932 (5) | 141 |
C15A—H15A···Cg5 | 0.93 | 2.84 | 3.528 (5) | 131 |
C4B—H4BA···Cg2 | 0.93 | 2.91 | 3.607 (5) | 133 |
C12B—H12B···Cg4v | 0.93 | 2.90 | 3.597 (6) | 133 |
Symmetry codes: (i) −x, −y−1, −z−1; (ii) x, y−1, z; (iii) x, −y−3/2, z−1/2; (iv) −x+1, y−1/2, −z−1/2; (v) x, y+1, z. |