4-(2,6-Di­methyl­phenoxy)­phthalo­nitrile

In the title compound, C₁₆H₁₂N₂O, two benzene rings are linked by an O atom. One of the benzene rings carries two cyano groups. The compound crystallizes with two independent mol­ecules in the asymmetric unit. The crystal structure is stabilized by weak van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.039
• wR factor = 0.113
• Data-to-parameter ratio = 7.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.70
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.62 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C12B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C10A
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C9B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C10B
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C14B
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C4A    -   C7A    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C5A    -   C8A    ...       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C3B    -   C7B    ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C4B    -   C8B    ...       1.44 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         27
            C2B -C3B -C7B -N1B   -83.00 19.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         28
            C4B -C3B -C7B -N1B    97.00 19.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         29
            C3A -C4A -C7A -N1A   114.00 20.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         30
            C5A -C4A -C7A -N1A   -64.00 20.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         31
            C5B -C4B -C8B -N2B   -18.00  9.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         32
            C3B -C4B -C8B -N2B   162.00  9.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         33
            C6A -C5A -C8A -N2A  -144.00  6.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         34
            C4A -C5A -C8A -N2A    34.00  6.00   1.555   1.555   1.555   1.555
PLAT732_ALERT_1_C Angle   Calc    121.1(9), Rep    121.0(4) ......       2.25 su-Rat
              C13B -C12B -C11B    1.555   1.555   1.555

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.99
           From the CIF: _reflns_number_total               2681
           Count of symmetry unique reflns         2694
           Completeness (_total/calc)             99.52%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 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
   9 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1998).

4-(2,6-dimethylphenoxy)phthalonitrile

Crystal data

C16H12N2O	Z = 2
Mr = 248.28	F(000) = 260
Triclinic, P1	Dx = 1.204 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.160 (5) Å	Cell parameters from 10590 reflections
b = 8.451 (5) Å	θ = 1.9–29.3°
c = 11.629 (5) Å	µ = 0.08 mm^−1
α = 97.921 (5)°	T = 293 K
β = 108.234 (5)°	Prism, colourless
γ = 110.548 (5)°	0.5 × 0.4 × 0.25 mm
V = 685.0 (7) Å^3

Data collection

Stoe IPDS-2 diffractometer	2681 independent reflections
Radiation source: fine-focus sealed tube	2415 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.9°
ω scans	h = −10→10
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −10→9
Tmin = 0.964, Tmax = 0.981	l = −14→14
9887 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0767P)^2 + 0.0109P] where P = (Fo^2 + 2Fc^2)/3
2681 reflections	(Δ/σ)max < 0.001
348 parameters	Δρmax = 0.15 e Å^−3
3 restraints	Δρmin = −0.13 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
C1B	0.1708 (3)	0.3762 (3)	0.9003 (2)	0.0610 (5)
C1A	0.3880 (3)	0.6632 (3)	0.4943 (2)	0.0573 (4)
C2B	0.1452 (3)	0.2139 (3)	0.9215 (2)	0.0627 (5)
H2B	0.1695	0.1342	0.8735	0.075*
C2A	0.5702 (3)	0.7344 (3)	0.5856 (2)	0.0680 (6)
H2A	0.6711	0.7362	0.5639	0.082*
C3B	0.0824 (3)	0.1724 (3)	1.0163 (2)	0.0595 (5)
C3A	0.6013 (3)	0.8026 (4)	0.7087 (2)	0.0757 (7)
H3A	0.7238	0.8495	0.7703	0.091*
C4B	0.0456 (3)	0.2921 (3)	1.08783 (19)	0.0592 (5)
C4A	0.4526 (3)	0.8026 (3)	0.7424 (2)	0.0676 (5)
C5B	0.0727 (3)	0.4532 (3)	1.0641 (2)	0.0659 (5)
H5B	0.0490	0.5336	1.1120	0.079*
C5A	0.2698 (3)	0.7272 (3)	0.6499 (2)	0.0633 (5)
C6B	0.1340 (3)	0.4958 (3)	0.9708 (2)	0.0664 (5)
H6B	0.1507	0.6041	0.9550	0.080*
C6A	0.2370 (3)	0.6565 (3)	0.5266 (2)	0.0632 (5)
H6A	0.1139	0.6046	0.4654	0.076*
C7B	0.0554 (4)	0.0043 (3)	1.0398 (2)	0.0690 (6)
C7A	0.4871 (5)	0.8840 (5)	0.8687 (3)	0.0911 (8)
C8B	−0.0185 (3)	0.2510 (3)	1.1868 (2)	0.0676 (5)
C8A	0.1154 (4)	0.7293 (5)	0.6828 (3)	0.0835 (7)
C9B	0.2681 (4)	0.3169 (3)	0.7332 (2)	0.0650 (5)
C9A	0.4920 (3)	0.6146 (3)	0.32842 (19)	0.0591 (5)
C10B	0.1243 (5)	0.2081 (4)	0.6205 (3)	0.0874 (8)
C10A	0.5608 (4)	0.4875 (4)	0.3310 (3)	0.0765 (6)
C11B	0.1756 (11)	0.1058 (5)	0.5450 (4)	0.135 (2)
H11B	0.0865	0.0294	0.4670	0.161*
C11A	0.7003 (5)	0.5048 (5)	0.2842 (4)	0.0998 (10)
H11A	0.7498	0.4211	0.2844	0.120*
C12B	0.3645 (15)	0.1199 (8)	0.5884 (8)	0.155 (3)
H12B	0.3977	0.0504	0.5390	0.187*
C12A	0.7660 (5)	0.6420 (6)	0.2379 (4)	0.1020 (10)
H12A	0.8613	0.6518	0.2080	0.122*
C13B	0.4938 (10)	0.2301 (8)	0.6977 (7)	0.136 (2)
H13B	0.6171	0.2383	0.7232	0.163*
C13A	0.6947 (4)	0.7658 (4)	0.2344 (3)	0.0886 (8)
H13A	0.7399	0.8576	0.2008	0.106*
C14B	0.4514 (5)	0.3304 (5)	0.7728 (4)	0.0940 (9)
C14A	0.5546 (3)	0.7554 (3)	0.2810 (2)	0.0657 (5)
C15B	−0.0685 (6)	0.2034 (7)	0.5815 (4)	0.1346 (18)
H15A	−0.1495	0.1060	0.6005	0.202*
H15B	−0.1190	0.1899	0.4925	0.202*
H15C	−0.0621	0.3111	0.6262	0.202*
C15A	0.4856 (7)	0.3374 (5)	0.3833 (5)	0.1179 (13)
H15D	0.5566	0.3712	0.4726	0.177*
H15E	0.4982	0.2371	0.3440	0.177*
H15F	0.3540	0.3080	0.3668	0.177*
C16B	0.6007 (7)	0.4559 (9)	0.8976 (6)	0.1441 (18)
H16A	0.6018	0.3967	0.9624	0.216*
H16B	0.5723	0.5548	0.9174	0.216*
H16C	0.7231	0.4961	0.8924	0.216*
C16A	0.4764 (5)	0.8899 (4)	0.2778 (3)	0.0895 (8)
H16D	0.3409	0.8330	0.2516	0.134*
H16E	0.5065	0.9533	0.2194	0.134*
H16F	0.5311	0.9703	0.3604	0.134*
N1B	0.0319 (5)	−0.1293 (4)	1.0571 (3)	0.0961 (8)
N1A	0.5133 (7)	0.9508 (7)	0.9684 (3)	0.1353 (14)
N2B	−0.0676 (4)	0.2231 (4)	1.2660 (3)	0.0881 (6)
N2A	−0.0024 (5)	0.7378 (7)	0.7127 (4)	0.1277 (14)
O1B	0.2304 (3)	0.4304 (2)	0.80915 (16)	0.0739 (4)
O1A	0.3439 (2)	0.5978 (2)	0.36961 (14)	0.0688 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1B	0.0660 (11)	0.0631 (11)	0.0546 (10)	0.0263 (9)	0.0240 (9)	0.0192 (9)
C1A	0.0544 (10)	0.0621 (11)	0.0575 (10)	0.0243 (8)	0.0227 (8)	0.0211 (9)
C2B	0.0718 (12)	0.0618 (12)	0.0613 (11)	0.0320 (10)	0.0298 (10)	0.0172 (9)
C2A	0.0508 (11)	0.0877 (15)	0.0668 (12)	0.0285 (10)	0.0250 (10)	0.0222 (11)
C3B	0.0582 (10)	0.0594 (11)	0.0604 (11)	0.0241 (9)	0.0225 (9)	0.0180 (9)
C3A	0.0540 (11)	0.1030 (19)	0.0627 (12)	0.0287 (12)	0.0185 (10)	0.0227 (12)
C4B	0.0547 (10)	0.0627 (11)	0.0562 (10)	0.0219 (9)	0.0209 (8)	0.0136 (9)
C4A	0.0689 (13)	0.0802 (15)	0.0602 (12)	0.0333 (11)	0.0285 (10)	0.0258 (11)
C5B	0.0740 (13)	0.0638 (12)	0.0646 (12)	0.0333 (10)	0.0296 (10)	0.0137 (10)
C5A	0.0627 (11)	0.0725 (13)	0.0686 (12)	0.0327 (10)	0.0335 (10)	0.0301 (10)
C6B	0.0791 (14)	0.0587 (11)	0.0662 (12)	0.0325 (10)	0.0291 (11)	0.0194 (10)
C6A	0.0517 (10)	0.0731 (13)	0.0655 (12)	0.0258 (9)	0.0229 (9)	0.0223 (10)
C7B	0.0794 (14)	0.0665 (14)	0.0738 (13)	0.0345 (11)	0.0389 (11)	0.0247 (11)
C7A	0.0901 (18)	0.116 (2)	0.0674 (16)	0.0399 (16)	0.0344 (14)	0.0256 (15)
C8B	0.0674 (12)	0.0662 (12)	0.0703 (13)	0.0247 (10)	0.0331 (11)	0.0156 (10)
C8A	0.0750 (15)	0.122 (2)	0.0763 (15)	0.0558 (15)	0.0378 (13)	0.0357 (15)
C9B	0.0808 (13)	0.0630 (11)	0.0650 (12)	0.0330 (10)	0.0384 (11)	0.0273 (10)
C9A	0.0604 (11)	0.0598 (11)	0.0581 (10)	0.0242 (9)	0.0260 (9)	0.0148 (9)
C10B	0.120 (2)	0.0665 (14)	0.0661 (14)	0.0215 (14)	0.0410 (15)	0.0247 (11)
C10A	0.0868 (16)	0.0690 (14)	0.0819 (15)	0.0424 (13)	0.0319 (13)	0.0218 (12)
C11B	0.248 (6)	0.074 (2)	0.083 (2)	0.047 (3)	0.088 (3)	0.0255 (16)
C11A	0.104 (2)	0.110 (2)	0.106 (2)	0.067 (2)	0.0467 (19)	0.0183 (19)
C12B	0.308 (9)	0.117 (3)	0.189 (5)	0.142 (5)	0.200 (7)	0.097 (4)
C12A	0.099 (2)	0.121 (3)	0.099 (2)	0.0487 (19)	0.0595 (19)	0.013 (2)
C13B	0.195 (5)	0.142 (4)	0.191 (5)	0.123 (4)	0.146 (5)	0.099 (4)
C13A	0.0926 (18)	0.0895 (18)	0.0790 (16)	0.0197 (14)	0.0479 (15)	0.0246 (13)
C14B	0.0932 (19)	0.105 (2)	0.120 (2)	0.0564 (17)	0.0570 (18)	0.064 (2)
C14A	0.0745 (13)	0.0576 (11)	0.0582 (11)	0.0229 (10)	0.0239 (10)	0.0139 (9)
C15B	0.086 (2)	0.144 (4)	0.111 (3)	0.003 (2)	0.006 (2)	0.043 (3)
C15A	0.134 (3)	0.087 (2)	0.149 (4)	0.057 (2)	0.050 (3)	0.061 (2)
C16B	0.087 (2)	0.161 (4)	0.154 (4)	0.046 (2)	0.012 (2)	0.053 (4)
C16A	0.108 (2)	0.0645 (14)	0.0917 (18)	0.0404 (14)	0.0284 (16)	0.0229 (13)
N1B	0.125 (2)	0.0793 (15)	0.117 (2)	0.0533 (14)	0.0676 (17)	0.0475 (15)
N1A	0.153 (3)	0.170 (4)	0.0723 (17)	0.062 (3)	0.0465 (19)	0.0112 (19)
N2B	0.0994 (16)	0.0877 (15)	0.0875 (14)	0.0333 (13)	0.0548 (13)	0.0273 (12)
N2A	0.101 (2)	0.217 (4)	0.115 (2)	0.096 (3)	0.0648 (18)	0.060 (3)
O1B	0.1018 (12)	0.0667 (9)	0.0711 (10)	0.0403 (9)	0.0464 (9)	0.0286 (8)
O1A	0.0575 (8)	0.0816 (10)	0.0618 (8)	0.0239 (7)	0.0245 (7)	0.0148 (7)

Geometric parameters (Å, º)

C1B—O1B	1.367 (3)	C9A—C14A	1.382 (3)
C1B—C2B	1.382 (3)	C9A—O1A	1.404 (3)
C1B—C6B	1.387 (3)	C10B—C11B	1.403 (6)
C1A—O1A	1.360 (3)	C10B—C15B	1.479 (6)
C1A—C2A	1.381 (3)	C10A—C11A	1.380 (5)
C1A—C6A	1.382 (3)	C10A—C15A	1.502 (5)
C2B—C3B	1.391 (3)	C11B—C12B	1.418 (10)
C2B—H2B	0.9300	C11B—H11B	0.9300
C2A—C3A	1.375 (4)	C11A—C12A	1.355 (6)
C2A—H2A	0.9300	C11A—H11A	0.9300
C3B—C4B	1.394 (3)	C12B—C13B	1.320 (11)
C3B—C7B	1.437 (3)	C12B—H12B	0.9300
C3A—C4A	1.386 (3)	C12A—C13A	1.363 (6)
C3A—H3A	0.9300	C12A—H12A	0.9300
C4B—C5B	1.382 (3)	C13B—C14B	1.338 (6)
C4B—C8B	1.441 (3)	C13B—H13B	0.9300
C4A—C5A	1.389 (3)	C13A—C14A	1.392 (4)
C4A—C7A	1.428 (4)	C13A—H13A	0.9300
C5B—C6B	1.370 (3)	C14B—C16B	1.510 (7)
C5B—H5B	0.9300	C14A—C16A	1.485 (4)
C5A—C6A	1.377 (3)	C15B—H15A	0.9600
C5A—C8A	1.432 (3)	C15B—H15B	0.9600
C6B—H6B	0.9300	C15B—H15C	0.9600
C6A—H6A	0.9300	C15A—H15D	0.9600
C7B—N1B	1.134 (4)	C15A—H15E	0.9600
C7A—N1A	1.134 (5)	C15A—H15F	0.9600
C8B—N2B	1.136 (3)	C16B—H16A	0.9600
C8A—N2A	1.140 (4)	C16B—H16B	0.9600
C9B—C10B	1.374 (4)	C16B—H16C	0.9600
C9B—C14B	1.377 (4)	C16A—H16D	0.9600
C9B—O1B	1.392 (3)	C16A—H16E	0.9600
C9A—C10A	1.375 (3)	C16A—H16F	0.9600
O1B—C1B—C2B	123.61 (19)	C11A—C10A—C15A	122.2 (3)
O1B—C1B—C6B	115.2 (2)	C10B—C11B—C12B	119.5 (5)
C2B—C1B—C6B	121.2 (2)	C10B—C11B—H11B	120.2
O1A—C1A—C2A	123.90 (19)	C12B—C11B—H11B	120.2
O1A—C1A—C6A	115.71 (18)	C12A—C11A—C10A	120.9 (3)
C2A—C1A—C6A	120.4 (2)	C12A—C11A—H11A	119.5
C1B—C2B—C3B	118.62 (19)	C10A—C11A—H11A	119.5
C1B—C2B—H2B	120.7	C13B—C12B—C11B	121.0 (4)
C3B—C2B—H2B	120.7	C13B—C12B—H12B	119.5
C3A—C2A—C1A	119.6 (2)	C11B—C12B—H12B	119.5
C3A—C2A—H2A	120.2	C11A—C12A—C13A	121.2 (3)
C1A—C2A—H2A	120.2	C11A—C12A—H12A	119.4
C2B—C3B—C4B	120.5 (2)	C13A—C12A—H12A	119.4
C2B—C3B—C7B	119.3 (2)	C12B—C13B—C14B	121.5 (6)
C4B—C3B—C7B	120.2 (2)	C12B—C13B—H13B	119.2
C2A—C3A—C4A	120.9 (2)	C14B—C13B—H13B	119.2
C2A—C3A—H3A	119.5	C12A—C13A—C14A	120.3 (3)
C4A—C3A—H3A	119.5	C12A—C13A—H13A	119.8
C5B—C4B—C3B	119.40 (19)	C14A—C13A—H13A	119.8
C5B—C4B—C8B	119.59 (19)	C13B—C14B—C9B	118.4 (5)
C3B—C4B—C8B	121.0 (2)	C13B—C14B—C16B	120.9 (5)
C3A—C4A—C5A	118.7 (2)	C9B—C14B—C16B	120.7 (4)
C3A—C4A—C7A	120.8 (2)	C9A—C14A—C13A	117.0 (2)
C5A—C4A—C7A	120.4 (2)	C9A—C14A—C16A	122.3 (2)
C6B—C5B—C4B	120.8 (2)	C13A—C14A—C16A	120.7 (3)
C6B—C5B—H5B	119.6	C10B—C15B—H15A	109.5
C4B—C5B—H5B	119.6	C10B—C15B—H15B	109.5
C6A—C5A—C4A	120.7 (2)	H15A—C15B—H15B	109.5
C6A—C5A—C8A	119.9 (2)	C10B—C15B—H15C	109.5
C4A—C5A—C8A	119.4 (2)	H15A—C15B—H15C	109.5
C5B—C6B—C1B	119.5 (2)	H15B—C15B—H15C	109.5
C5B—C6B—H6B	120.3	C10A—C15A—H15D	109.5
C1B—C6B—H6B	120.3	C10A—C15A—H15E	109.5
C5A—C6A—C1A	119.6 (2)	H15D—C15A—H15E	109.5
C5A—C6A—H6A	120.2	C10A—C15A—H15F	109.5
C1A—C6A—H6A	120.2	H15D—C15A—H15F	109.5
N1B—C7B—C3B	179.1 (3)	H15E—C15A—H15F	109.5
N1A—C7A—C4A	178.8 (4)	C14B—C16B—H16A	109.5
N2B—C8B—C4B	178.2 (3)	C14B—C16B—H16B	109.5
N2A—C8A—C5A	177.0 (4)	H16A—C16B—H16B	109.5
C10B—C9B—C14B	124.5 (3)	C14B—C16B—H16C	109.5
C10B—C9B—O1B	118.1 (3)	H16A—C16B—H16C	109.5
C14B—C9B—O1B	117.3 (3)	H16B—C16B—H16C	109.5
C10A—C9A—C14A	123.3 (2)	C14A—C16A—H16D	109.5
C10A—C9A—O1A	119.1 (2)	C14A—C16A—H16E	109.5
C14A—C9A—O1A	117.46 (19)	H16D—C16A—H16E	109.5
C9B—C10B—C11B	115.0 (4)	C14A—C16A—H16F	109.5
C9B—C10B—C15B	122.0 (3)	H16D—C16A—H16F	109.5
C11B—C10B—C15B	123.0 (4)	H16E—C16A—H16F	109.5
C9A—C10A—C11A	117.3 (3)	C1B—O1B—C9B	118.67 (18)
C9A—C10A—C15A	120.5 (3)	C1A—O1A—C9A	118.77 (16)
O1B—C1B—C2B—C3B	−179.5 (2)	O1B—C9B—C10B—C11B	175.9 (2)
C6B—C1B—C2B—C3B	−0.4 (3)	C14B—C9B—C10B—C15B	−178.1 (3)
O1A—C1A—C2A—C3A	177.8 (2)	O1B—C9B—C10B—C15B	−2.8 (4)
C6A—C1A—C2A—C3A	−1.5 (4)	C14A—C9A—C10A—C11A	0.5 (4)
C1B—C2B—C3B—C4B	0.2 (3)	O1A—C9A—C10A—C11A	177.0 (2)
C1B—C2B—C3B—C7B	−179.9 (2)	C14A—C9A—C10A—C15A	−179.7 (3)
C1A—C2A—C3A—C4A	−0.6 (4)	O1A—C9A—C10A—C15A	−3.1 (4)
C2B—C3B—C4B—C5B	−0.2 (3)	C9B—C10B—C11B—C12B	0.4 (4)
C7B—C3B—C4B—C5B	179.9 (2)	C15B—C10B—C11B—C12B	179.0 (3)
C2B—C3B—C4B—C8B	−179.6 (2)	C9A—C10A—C11A—C12A	0.1 (5)
C7B—C3B—C4B—C8B	0.4 (3)	C15A—C10A—C11A—C12A	−179.8 (4)
C2A—C3A—C4A—C5A	2.0 (4)	C10B—C11B—C12B—C13B	−1.3 (6)
C2A—C3A—C4A—C7A	−175.8 (3)	C10A—C11A—C12A—C13A	−1.0 (6)
C3B—C4B—C5B—C6B	0.4 (3)	C11B—C12B—C13B—C14B	1.2 (7)
C8B—C4B—C5B—C6B	179.8 (2)	C11A—C12A—C13A—C14A	1.3 (5)
C3A—C4A—C5A—C6A	−1.1 (4)	C12B—C13B—C14B—C9B	−0.2 (6)
C7A—C4A—C5A—C6A	176.6 (3)	C12B—C13B—C14B—C16B	−180.0 (4)
C3A—C4A—C5A—C8A	−178.8 (3)	C10B—C9B—C14B—C13B	−0.7 (4)
C7A—C4A—C5A—C8A	−1.0 (4)	O1B—C9B—C14B—C13B	−176.0 (3)
C4B—C5B—C6B—C1B	−0.6 (4)	C10B—C9B—C14B—C16B	179.1 (3)
O1B—C1B—C6B—C5B	179.7 (2)	O1B—C9B—C14B—C16B	3.7 (4)
C2B—C1B—C6B—C5B	0.6 (4)	C10A—C9A—C14A—C13A	−0.1 (3)
C4A—C5A—C6A—C1A	−1.0 (4)	O1A—C9A—C14A—C13A	−176.8 (2)
C8A—C5A—C6A—C1A	176.6 (2)	C10A—C9A—C14A—C16A	179.2 (3)
O1A—C1A—C6A—C5A	−177.1 (2)	O1A—C9A—C14A—C16A	2.6 (3)
C2A—C1A—C6A—C5A	2.3 (3)	C12A—C13A—C14A—C9A	−0.7 (4)
C2B—C3B—C7B—N1B	−83 (19)	C12A—C13A—C14A—C16A	179.9 (3)
C4B—C3B—C7B—N1B	97 (19)	C2B—C1B—O1B—C9B	−0.1 (3)
C3A—C4A—C7A—N1A	114 (20)	C6B—C1B—O1B—C9B	−179.2 (2)
C5A—C4A—C7A—N1A	−64 (20)	C10B—C9B—O1B—C1B	93.1 (3)
C5B—C4B—C8B—N2B	−18 (9)	C14B—C9B—O1B—C1B	−91.2 (3)
C3B—C4B—C8B—N2B	162 (9)	C2A—C1A—O1A—C9A	−5.0 (3)
C6A—C5A—C8A—N2A	−144 (6)	C6A—C1A—O1A—C9A	174.35 (19)
C4A—C5A—C8A—N2A	34 (6)	C10A—C9A—O1A—C1A	87.1 (3)
C14B—C9B—C10B—C11B	0.5 (4)	C14A—C9A—O1A—C1A	−96.1 (2)