4-(8-Quinolinoxy)­phthalo­nitrile

The title compound, C₁₇H₉N₃O, cyrstallizes with two mol­ecules in the asymmetric unit. Both independent mol­ecules have essentially the same geometry. The angles between the planes of the quinoline group and the phenyl ring of the phthalo­nitrile group in the two mol­ecules are 84.36 (4) and 83.69 (4)°.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.115
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.54
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12A   -   C16A     =       5.32 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12B   -   C16B     =       6.49 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C12A   -   C16A     =       1.45 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C13A   -   C17A     =       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C12B   -   C16B     =       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C13B   -   C17B     =       1.44 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

Substituted phthalonitriles have been used as starting materials for phthalocyanines (McKeown, 1988). In addition to their extensive use as dyes and pigments, phthalocyanines have found widespread applications in catalysis, in optical recording, in photoconductive materials, in photodynamic therapy and as chemical sensors (Leznoff, 1993).

Fig. 1 shows a perspective view of the asymmetric unit of the title compound, (I), with the numbering scheme. The C10—O1 bond distance is 1.3779 (19) Å in molecule A and 1.3717 (19) Å in molecule B. The triple C≡N bond distances in molecules A and B are in good agreement with those in a related structure in the literature (Karadaı et al., 2003). The quinoline group is essentially planar. The angle between the least-squares planes C1–C9/N1 and C10–C15 is 84.36 (4)° in molecule A and 83.69 (4)° in molecule B; the maximun deviation deviation from planarity being -0.041 (2) Å for C2A atom in the C1A–C9A/N1A ring.

S2. Experimental

8-Quinolinol (1.31 g, 9.03 mmol) and 4-nitrophthalonitrile (1.36 g, 7.86 mmol) were dissolved in dry dimethylformamide (40 ml). After stirring for 30 min at room temperature, dry fine-powdered potassium cabonate (3.25 g, 23.55 mmol) was added portionwise over 2 h with efficent stirring. The reaction was stirred for 24 h at room temperature and poured into ice-water (200 g). The product was filtered off and washed with (5% w/w) NaOH solution and water until the filtrate was neutral. Recrystallizaiton from ethanol gave a white product; yield 1.30 g (6.03%). Single crystals were obtained in ethanol at room temperature via slow evaporation. Calculated: C 75.27, H3.34, N 15.49%; found: C 75.25, H 3.30, N 15.53%. IR data (Vmax/cm^-1): 3060–3020 (Ar—CH), 2210 (CN), 1668, 1596, 1560, 1480, 1464, 1416, 1384, 1364, 1312, 1276, 1236, 1188, 1160, 1128, 1090, 1070, 1050, 1024, 990, 944, 880, 825, 790, 772, 736, 725, 705, 660, 640, 625, 575, 525. ¹H NMR (acetone-d₆): 7.30–8.02 (m, 7H); 8.48 (d, 1H); 8.80 (d, 1H). ¹³C NMR (acetone-d₆): 109.03, 116.11, 116.67, 117.92, 122.08, 122.29, 123.21, 127.51, 127.79, 131.39, 136.49, 137.24, 141.80, 150.28, 151.49, 164.03.

S3. Refinement

H atoms were located in a difference Fourier map and refined independently with isotropic thermal parameters. The final C—H distances ranged from 0.94 (2) to 1.01 (2) Å.

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

Figures

Fig. 1. The structure of the title compound, showing %50 probability displacement ellipsoids and the atom-numbering scheme.

4-(8-Quinolinoxy)phthalonitrile

Crystal data

C17H9N3O	Z = 8
Mr = 271.28	F(000) = 1120
Monoclinic, P21/c	Dx = 1.360 Mg m^−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.7510 (11) Å	µ = 0.09 mm^−1
b = 14.7398 (12) Å	T = 150 K
c = 15.0377 (13) Å	Plate, colourless
β = 110.324 (1)°	0.36 × 0.27 × 0.05 mm
V = 2650.3 (4) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	6214 independent reflections
Radiation source: sealed tube	4311 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 28.7°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick 1996)	h = −16→16
Tmin = 0.941, Tmax = 0.996	k = −18→19
21956 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	All H-atom parameters refined
S = 1.03	w = 1/[σ^2(Fo^2) + (0.052P)^2 + 0.6288P] where P = (Fo^2 + 2Fc^2)/3
6214 reflections	(Δ/σ)max < 0.001
451 parameters	Δρmax = 0.51 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
H6A	1.0771 (14)	1.0076 (13)	0.8750 (12)	0.038 (5)*
H5A	1.2411 (16)	0.9595 (13)	0.8428 (13)	0.043 (5)*
H3A	1.2002 (17)	0.6490 (13)	0.8023 (14)	0.046 (5)*
H4A	1.2665 (15)	0.8101 (12)	0.8135 (13)	0.040 (5)*
H1A	0.8889 (16)	0.6022 (13)	0.8206 (13)	0.046 (5)*
H2A	1.0527 (16)	0.5441 (14)	0.8023 (14)	0.050 (6)*
H7A	0.7274 (13)	0.9130 (11)	0.9030 (12)	0.026 (4)*
H6B	0.4115 (15)	0.8942 (13)	−0.0077 (14)	0.043 (5)*
H3B	0.7255 (18)	0.7973 (13)	0.3574 (15)	0.052 (6)*
H1B	0.4312 (16)	0.8126 (13)	0.4103 (14)	0.046 (5)*
H4B	0.7124 (17)	0.8291 (13)	0.1886 (13)	0.046 (5)*
H5B	0.6070 (16)	0.8695 (14)	0.0338 (14)	0.053 (6)*
H2B	0.6274 (18)	0.7869 (14)	0.4647 (16)	0.059 (6)*
H9A	0.6837 (15)	0.9233 (12)	0.5783 (13)	0.039 (5)*
H8A	0.8617 (15)	0.9053 (12)	0.6926 (13)	0.041 (5)*
H7B	0.0911 (14)	0.9066 (12)	0.0865 (12)	0.032 (4)*
H9B	0.1812 (14)	0.5964 (12)	0.0568 (12)	0.033 (4)*
H8B	0.3169 (15)	0.7130 (12)	0.0810 (12)	0.035 (5)*
O1B	0.29045 (9)	0.88782 (7)	0.09659 (8)	0.0325 (3)
O1A	0.91311 (9)	0.90922 (8)	0.87955 (8)	0.0329 (3)
C4A	1.11853 (13)	0.76258 (12)	0.82389 (11)	0.0313 (4)
C12A	0.61234 (12)	0.92017 (10)	0.76770 (11)	0.0275 (3)
C12B	0.03045 (12)	0.77488 (11)	0.07067 (10)	0.0260 (3)
C11B	0.11045 (13)	0.84189 (11)	0.08309 (10)	0.0265 (3)
C14A	0.69313 (13)	0.91928 (11)	0.64444 (12)	0.0311 (4)
C13A	0.59922 (13)	0.92478 (10)	0.67105 (11)	0.0281 (3)
N1A	0.93409 (11)	0.73019 (10)	0.83528 (9)	0.0326 (3)
C9A	1.01783 (13)	0.78944 (11)	0.83780 (10)	0.0282 (3)
C13B	0.05656 (13)	0.68333 (11)	0.06192 (10)	0.0275 (3)
C15A	0.79833 (14)	0.91029 (11)	0.71241 (12)	0.0313 (4)
C8A	1.00651 (12)	0.88255 (11)	0.85678 (10)	0.0285 (3)
C14B	0.16427 (14)	0.66018 (11)	0.06639 (11)	0.0308 (4)
C16A	0.51506 (14)	0.92081 (11)	0.79608 (12)	0.0321 (4)
N1B	0.41096 (12)	0.83712 (9)	0.28083 (10)	0.0343 (3)
C9B	0.46570 (13)	0.84459 (10)	0.21739 (12)	0.0286 (3)
C15B	0.24444 (14)	0.72749 (11)	0.07964 (12)	0.0310 (4)
C5A	1.19999 (14)	0.82842 (13)	0.82587 (12)	0.0367 (4)
N2A	0.43757 (13)	0.91940 (11)	0.81835 (12)	0.0453 (4)
C8B	0.40436 (12)	0.86788 (11)	0.12188 (11)	0.0291 (3)
N3B	−0.09994 (14)	0.56323 (11)	0.03184 (12)	0.0456 (4)
C16B	−0.08082 (14)	0.79890 (11)	0.06641 (11)	0.0316 (4)
C10A	0.81049 (13)	0.91006 (10)	0.80766 (11)	0.0285 (3)
N2B	−0.16893 (12)	0.81843 (11)	0.06417 (11)	0.0429 (4)
C17A	0.48962 (14)	0.93467 (12)	0.60115 (12)	0.0340 (4)
C7B	0.45435 (14)	0.87757 (13)	0.05578 (13)	0.0358 (4)
C11A	0.71796 (13)	0.91426 (11)	0.83610 (12)	0.0301 (4)
C17B	−0.02901 (14)	0.61542 (12)	0.04582 (11)	0.0327 (4)
C10B	0.21740 (12)	0.81722 (11)	0.08768 (11)	0.0272 (3)
C4B	0.58294 (13)	0.83046 (11)	0.24209 (12)	0.0326 (4)
C7A	1.08690 (14)	0.94396 (12)	0.86105 (12)	0.0343 (4)
C5B	0.63295 (14)	0.83950 (12)	0.17202 (13)	0.0384 (4)
C1A	0.95151 (16)	0.64430 (12)	0.82104 (12)	0.0369 (4)
C1B	0.47268 (17)	0.81627 (13)	0.36850 (14)	0.0414 (4)
N3A	0.40145 (13)	0.94165 (12)	0.54542 (12)	0.0484 (4)
C6A	1.18454 (14)	0.91693 (13)	0.84374 (13)	0.0387 (4)
C2A	1.04955 (17)	0.61071 (13)	0.80988 (12)	0.0415 (4)
C3A	1.13241 (16)	0.66930 (13)	0.81058 (12)	0.0379 (4)
C6B	0.57067 (15)	0.86318 (13)	0.08191 (14)	0.0401 (4)
C2B	0.58950 (17)	0.80187 (13)	0.40044 (14)	0.0443 (5)
C3B	0.64430 (16)	0.80849 (12)	0.33797 (14)	0.0403 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1B	0.0215 (5)	0.0285 (6)	0.0450 (7)	−0.0003 (4)	0.0086 (5)	−0.0034 (5)
O1A	0.0244 (6)	0.0405 (7)	0.0328 (6)	0.0030 (5)	0.0087 (5)	−0.0037 (5)
C4A	0.0293 (8)	0.0412 (10)	0.0206 (7)	0.0077 (7)	0.0053 (6)	0.0021 (7)
C12A	0.0249 (8)	0.0224 (8)	0.0367 (9)	0.0006 (6)	0.0126 (7)	0.0013 (6)
C12B	0.0238 (8)	0.0336 (9)	0.0202 (7)	0.0014 (6)	0.0074 (6)	−0.0012 (6)
C11B	0.0252 (8)	0.0288 (9)	0.0242 (8)	0.0023 (6)	0.0069 (6)	−0.0029 (6)
C14A	0.0303 (9)	0.0329 (9)	0.0294 (9)	−0.0011 (7)	0.0096 (7)	0.0039 (7)
C13A	0.0251 (8)	0.0237 (8)	0.0340 (8)	−0.0010 (6)	0.0083 (7)	0.0038 (6)
N1A	0.0334 (7)	0.0365 (8)	0.0254 (7)	−0.0031 (6)	0.0071 (6)	0.0007 (6)
C9A	0.0279 (8)	0.0355 (9)	0.0196 (7)	0.0042 (7)	0.0062 (6)	0.0020 (6)
C13B	0.0290 (8)	0.0319 (8)	0.0217 (7)	−0.0033 (7)	0.0088 (6)	−0.0010 (6)
C15A	0.0265 (8)	0.0363 (9)	0.0334 (9)	0.0002 (7)	0.0133 (7)	0.0028 (7)
C8A	0.0230 (8)	0.0371 (9)	0.0241 (8)	0.0049 (7)	0.0066 (6)	0.0019 (7)
C14B	0.0323 (9)	0.0276 (9)	0.0313 (8)	0.0010 (7)	0.0097 (7)	−0.0035 (7)
C16A	0.0300 (9)	0.0302 (9)	0.0360 (9)	0.0007 (7)	0.0116 (7)	0.0022 (7)
N1B	0.0362 (8)	0.0304 (8)	0.0387 (8)	−0.0044 (6)	0.0160 (7)	−0.0050 (6)
C9B	0.0266 (8)	0.0222 (8)	0.0372 (9)	−0.0031 (6)	0.0113 (7)	−0.0058 (6)
C15B	0.0231 (8)	0.0341 (9)	0.0351 (9)	0.0027 (7)	0.0092 (7)	−0.0041 (7)
C5A	0.0260 (9)	0.0534 (12)	0.0306 (9)	0.0073 (8)	0.0097 (7)	0.0046 (8)
N2A	0.0343 (8)	0.0511 (10)	0.0569 (10)	0.0004 (7)	0.0239 (8)	0.0023 (8)
C8B	0.0199 (7)	0.0275 (8)	0.0376 (9)	−0.0019 (6)	0.0073 (7)	−0.0070 (7)
N3B	0.0478 (9)	0.0424 (9)	0.0535 (10)	−0.0108 (8)	0.0261 (8)	−0.0038 (7)
C16B	0.0304 (9)	0.0352 (9)	0.0295 (8)	−0.0026 (7)	0.0109 (7)	−0.0013 (7)
C10A	0.0260 (8)	0.0244 (8)	0.0340 (8)	0.0003 (6)	0.0091 (7)	0.0007 (6)
N2B	0.0308 (8)	0.0542 (10)	0.0465 (9)	0.0013 (7)	0.0169 (7)	−0.0013 (7)
C17A	0.0288 (9)	0.0357 (9)	0.0374 (9)	−0.0030 (7)	0.0115 (8)	0.0084 (7)
C7B	0.0295 (9)	0.0433 (10)	0.0325 (9)	−0.0037 (7)	0.0082 (7)	−0.0071 (8)
C11A	0.0298 (8)	0.0299 (9)	0.0317 (9)	0.0018 (7)	0.0120 (7)	0.0009 (7)
C17B	0.0357 (9)	0.0348 (9)	0.0313 (8)	−0.0027 (8)	0.0163 (7)	−0.0025 (7)
C10B	0.0237 (8)	0.0309 (8)	0.0245 (7)	−0.0021 (6)	0.0053 (6)	−0.0032 (6)
C4B	0.0254 (8)	0.0276 (8)	0.0413 (9)	−0.0017 (6)	0.0071 (7)	−0.0056 (7)
C7A	0.0316 (9)	0.0335 (10)	0.0336 (9)	0.0039 (7)	0.0060 (7)	0.0044 (7)
C5B	0.0242 (9)	0.0420 (11)	0.0495 (11)	−0.0026 (7)	0.0132 (8)	−0.0086 (8)
C1A	0.0430 (10)	0.0370 (10)	0.0255 (8)	−0.0023 (8)	0.0054 (7)	0.0001 (7)
C1B	0.0518 (11)	0.0360 (10)	0.0395 (10)	−0.0070 (8)	0.0196 (9)	−0.0032 (8)
N3A	0.0317 (8)	0.0630 (11)	0.0461 (9)	−0.0035 (7)	0.0079 (7)	0.0171 (8)
C6A	0.0275 (9)	0.0469 (11)	0.0390 (10)	−0.0010 (8)	0.0081 (8)	0.0093 (8)
C2A	0.0524 (12)	0.0366 (10)	0.0288 (9)	0.0084 (9)	0.0057 (8)	−0.0047 (8)
C3A	0.0387 (10)	0.0468 (11)	0.0245 (8)	0.0135 (9)	0.0061 (7)	−0.0034 (7)
C6B	0.0325 (9)	0.0489 (11)	0.0420 (10)	−0.0046 (8)	0.0169 (8)	−0.0100 (8)
C2B	0.0494 (12)	0.0379 (10)	0.0360 (10)	−0.0058 (8)	0.0027 (9)	0.0025 (8)
C3B	0.0331 (10)	0.0321 (10)	0.0478 (11)	−0.0017 (7)	0.0040 (8)	−0.0011 (8)

Geometric parameters (Å, º)

O1B—C10B	1.3717 (19)	C9B—C8B	1.418 (2)
O1B—C8B	1.3990 (18)	C9B—C4B	1.425 (2)
O1A—C10A	1.3779 (19)	C15B—C10B	1.383 (2)
O1A—C8A	1.4048 (18)	C15B—H8B	0.942 (18)
C4A—C3A	1.409 (2)	C5A—C6A	1.360 (3)
C4A—C5A	1.414 (3)	C5A—H4A	0.968 (18)
C4A—C9A	1.427 (2)	C8B—C7B	1.362 (2)
C12A—C11A	1.385 (2)	C17B—N3B	1.150 (2)
C12A—C13A	1.406 (2)	C16B—N2B	1.149 (2)
C12A—C16A	1.445 (2)	C10A—C11A	1.389 (2)
C12B—C11B	1.385 (2)	C17A—N3A	1.150 (2)
C12B—C13B	1.407 (2)	C7B—C6B	1.412 (2)
C12B—C16B	1.442 (2)	C7B—H6B	0.952 (19)
C11B—C10B	1.390 (2)	C11A—H7A	0.971 (16)
C11B—H7B	0.991 (18)	C4B—C5B	1.415 (2)
C14A—C15A	1.382 (2)	C4B—C3B	1.419 (2)
C14A—C13A	1.391 (2)	C7A—C6A	1.415 (2)
C14A—H9A	0.961 (18)	C7A—H6A	0.978 (19)
C13A—C17A	1.435 (2)	C5B—C6B	1.357 (3)
N1A—C1A	1.316 (2)	C5B—H4B	0.968 (19)
N1A—C9A	1.370 (2)	C1A—C2A	1.408 (3)
C9A—C8A	1.419 (2)	C1A—H1A	1.01 (2)
C13B—C14B	1.394 (2)	C1B—C2B	1.413 (3)
C13B—C17B	1.438 (2)	C1B—H1B	0.953 (19)
C15A—C10A	1.386 (2)	C6A—H5A	0.96 (2)
C15A—H8A	0.956 (19)	C2A—C3A	1.362 (3)
C8A—C7A	1.352 (2)	C2A—H2A	0.99 (2)
C14B—C15B	1.388 (2)	C3A—H3A	0.96 (2)
C14B—H9B	0.987 (18)	C6B—H5B	0.99 (2)
C16A—N2A	1.148 (2)	C2B—C3B	1.355 (3)
N1B—C1B	1.316 (2)	C2B—H2B	0.94 (2)
N1B—C9B	1.368 (2)	C3B—H3B	0.99 (2)
C10B—O1B—C8B	118.22 (12)	O1B—C8B—C9B	118.77 (14)
C10A—O1A—C8A	117.76 (12)	N2B—C16B—C12B	179.14 (18)
C3A—C4A—C5A	123.02 (16)	O1A—C10A—C15A	123.07 (14)
C3A—C4A—C9A	117.09 (16)	O1A—C10A—C11A	115.83 (14)
C5A—C4A—C9A	119.89 (16)	C15A—C10A—C11A	121.06 (15)
C11A—C12A—C13A	120.46 (14)	N3A—C17A—C13A	179.22 (19)
C11A—C12A—C16A	119.62 (15)	C8B—C7B—C6B	119.59 (17)
C13A—C12A—C16A	119.92 (14)	C8B—C7B—H6B	120.5 (11)
C11B—C12B—C13B	120.63 (14)	C6B—C7B—H6B	120.0 (11)
C11B—C12B—C16B	119.88 (14)	C12A—C11A—C10A	119.02 (15)
C13B—C12B—C16B	119.50 (14)	C12A—C11A—H7A	120.6 (9)
C12B—C11B—C10B	118.96 (15)	C10A—C11A—H7A	120.4 (9)
C12B—C11B—H7B	120.6 (10)	N3B—C17B—C13B	177.83 (19)
C10B—C11B—H7B	120.4 (10)	O1B—C10B—C15B	123.55 (14)
C15A—C14A—C13A	120.30 (15)	O1B—C10B—C11B	115.32 (14)
C15A—C14A—H9A	120.7 (11)	C15B—C10B—C11B	121.07 (14)
C13A—C14A—H9A	118.9 (11)	C5B—C4B—C3B	123.12 (16)
C14A—C13A—C12A	119.31 (14)	C5B—C4B—C9B	119.70 (16)
C14A—C13A—C17A	120.80 (15)	C3B—C4B—C9B	117.18 (16)
C12A—C13A—C17A	119.88 (14)	C8A—C7A—C6A	120.25 (17)
C1A—N1A—C9A	116.36 (15)	C8A—C7A—H6A	120.0 (10)
N1A—C9A—C8A	119.30 (14)	C6A—C7A—H6A	119.7 (10)
N1A—C9A—C4A	123.48 (15)	C6B—C5B—C4B	120.61 (17)
C8A—C9A—C4A	117.21 (15)	C6B—C5B—H4B	119.7 (11)
C14B—C13B—C12B	119.43 (14)	C4B—C5B—H4B	119.7 (11)
C14B—C13B—C17B	121.00 (15)	N1A—C1A—C2A	124.39 (18)
C12B—C13B—C17B	119.54 (14)	N1A—C1A—H1A	114.5 (11)
C14A—C15A—C10A	119.73 (15)	C2A—C1A—H1A	121.1 (11)
C14A—C15A—H8A	119.1 (11)	N1B—C1B—C2B	124.65 (18)
C10A—C15A—H8A	121.2 (11)	N1B—C1B—H1B	113.4 (12)
C7A—C8A—O1A	119.60 (15)	C2B—C1B—H1B	121.9 (12)
C7A—C8A—C9A	121.90 (15)	C5A—C6A—C7A	120.24 (17)
O1A—C8A—C9A	118.27 (14)	C5A—C6A—H5A	117.6 (11)
C15B—C14B—C13B	119.74 (15)	C7A—C6A—H5A	122.2 (11)
C15B—C14B—H9B	121.0 (10)	C3A—C2A—C1A	119.66 (18)
C13B—C14B—H9B	119.2 (10)	C3A—C2A—H2A	124.6 (12)
N2A—C16A—C12A	178.57 (18)	C1A—C2A—H2A	115.8 (12)
C1B—N1B—C9B	116.42 (15)	C2A—C3A—C4A	118.97 (17)
N1B—C9B—C8B	119.34 (14)	C2A—C3A—H3A	122.1 (12)
N1B—C9B—C4B	123.33 (15)	C4A—C3A—H3A	119.0 (12)
C8B—C9B—C4B	117.32 (15)	C5B—C6B—C7B	120.68 (18)
C10B—C15B—C14B	120.17 (15)	C5B—C6B—H5B	119.6 (12)
C10B—C15B—H8B	119.2 (11)	C7B—C6B—H5B	119.7 (12)
C14B—C15B—H8B	120.6 (11)	C3B—C2B—C1B	119.34 (18)
C6A—C5A—C4A	120.44 (16)	C3B—C2B—H2B	121.4 (13)
C6A—C5A—H4A	120.2 (11)	C1B—C2B—H2B	119.2 (13)
C4A—C5A—H4A	119.4 (11)	C2B—C3B—C4B	119.07 (18)
C7B—C8B—O1B	118.99 (15)	C2B—C3B—H3B	121.5 (12)
C7B—C8B—C9B	122.08 (15)	C4B—C3B—H3B	119.4 (12)
C13B—C12B—C11B—C10B	−0.6 (2)	C8A—O1A—C10A—C15A	−18.0 (2)
C16B—C12B—C11B—C10B	179.54 (14)	C8A—O1A—C10A—C11A	164.43 (14)
C15A—C14A—C13A—C12A	−0.6 (2)	C14A—C15A—C10A—O1A	−174.26 (15)
C15A—C14A—C13A—C17A	179.63 (15)	C14A—C15A—C10A—C11A	3.2 (2)
C11A—C12A—C13A—C14A	2.8 (2)	O1B—C8B—C7B—C6B	176.05 (15)
C16A—C12A—C13A—C14A	−176.63 (15)	C9B—C8B—C7B—C6B	0.7 (3)
C11A—C12A—C13A—C17A	−177.42 (15)	C13A—C12A—C11A—C10A	−2.0 (2)
C16A—C12A—C13A—C17A	3.1 (2)	C16A—C12A—C11A—C10A	177.46 (15)
C1A—N1A—C9A—C8A	−177.42 (14)	O1A—C10A—C11A—C12A	176.62 (14)
C1A—N1A—C9A—C4A	1.4 (2)	C15A—C10A—C11A—C12A	−1.0 (2)
C3A—C4A—C9A—N1A	−2.5 (2)	C8B—O1B—C10B—C15B	−16.1 (2)
C5A—C4A—C9A—N1A	178.82 (14)	C8B—O1B—C10B—C11B	166.52 (13)
C3A—C4A—C9A—C8A	176.39 (14)	C14B—C15B—C10B—O1B	−176.97 (15)
C5A—C4A—C9A—C8A	−2.3 (2)	C14B—C15B—C10B—C11B	0.3 (2)
C11B—C12B—C13B—C14B	0.4 (2)	C12B—C11B—C10B—O1B	177.72 (13)
C16B—C12B—C13B—C14B	−179.77 (14)	C12B—C11B—C10B—C15B	0.3 (2)
C11B—C12B—C13B—C17B	−177.88 (14)	N1B—C9B—C4B—C5B	179.96 (15)
C16B—C12B—C13B—C17B	2.0 (2)	C8B—C9B—C4B—C5B	−0.3 (2)
C13A—C14A—C15A—C10A	−2.3 (2)	N1B—C9B—C4B—C3B	−0.6 (2)
C10A—O1A—C8A—C7A	112.85 (16)	C8B—C9B—C4B—C3B	179.09 (15)
C10A—O1A—C8A—C9A	−72.48 (18)	O1A—C8A—C7A—C6A	176.29 (14)
N1A—C9A—C8A—C7A	179.36 (15)	C9A—C8A—C7A—C6A	1.8 (2)
C4A—C9A—C8A—C7A	0.4 (2)	C3B—C4B—C5B—C6B	−178.10 (17)
N1A—C9A—C8A—O1A	4.8 (2)	C9B—C4B—C5B—C6B	1.3 (3)
C4A—C9A—C8A—O1A	−174.10 (13)	C9A—N1A—C1A—C2A	0.9 (2)
C12B—C13B—C14B—C15B	0.2 (2)	C9B—N1B—C1B—C2B	0.3 (3)
C17B—C13B—C14B—C15B	178.39 (15)	C4A—C5A—C6A—C7A	0.3 (3)
C1B—N1B—C9B—C8B	−179.31 (15)	C8A—C7A—C6A—C5A	−2.2 (3)
C1B—N1B—C9B—C4B	0.4 (2)	N1A—C1A—C2A—C3A	−2.1 (3)
C13B—C14B—C15B—C10B	−0.5 (2)	C1A—C2A—C3A—C4A	0.9 (2)
C3A—C4A—C5A—C6A	−176.67 (16)	C5A—C4A—C3A—C2A	179.86 (16)
C9A—C4A—C5A—C6A	2.0 (2)	C9A—C4A—C3A—C2A	1.2 (2)
C10B—O1B—C8B—C7B	109.17 (17)	C4B—C5B—C6B—C7B	−1.2 (3)
C10B—O1B—C8B—C9B	−75.34 (18)	C8B—C7B—C6B—C5B	0.2 (3)
N1B—C9B—C8B—C7B	179.07 (15)	N1B—C1B—C2B—C3B	−0.8 (3)
C4B—C9B—C8B—C7B	−0.7 (2)	C1B—C2B—C3B—C4B	0.5 (3)
N1B—C9B—C8B—O1B	3.7 (2)	C5B—C4B—C3B—C2B	179.52 (17)
C4B—C9B—C8B—O1B	−176.02 (13)	C9B—C4B—C3B—C2B	0.2 (2)