4,5-Bis(5-iso­propyl-2-methyl­phenoxy)­phthalo­nitrile

The phthalo­nitrile derivative, C₂₈H₂₆N₂O₂, contains three aromatic rings, which are mutually almost orthogonal. The structure is stabilized by π–π stacking interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.167
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       7.62 Ratio

Author Response: The crystal quality is not rich enough so we have run into this kind of problems.

PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       8.94 Ratio

Author Response: The crystal quality is not rich enough so we have run into this kind of problems.

PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for        C21

Author Response: The crystal quality is not rich enough so we have run into this kind of problems.

Alert level B
PLAT213_ALERT_2_B Atom C23B    has ADP max/min Ratio .............       4.40 prolat
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C17

Author Response: The crystal quality is not rich enough so we have run into this kind of problems.

PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C24

Author Response: The crystal quality is not rich enough so we have run into this kind of problems.

Alert level C
CHEMW01_ALERT_1_C  The difference between the given and expected weight for
            compound is greater 1 mass unit. Check that all hydrogen
            atoms have been taken into account.
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.72 mm
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT213_ALERT_2_C Atom C25B    has ADP max/min Ratio .............       3.90 prolat
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C18
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20

Author Response: The crystal quality is not rich enough so we have run into this kind of problems.

PLAT301_ALERT_3_C Main Residue  Disorder .........................      11.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C15    -   C17    ...       1.38 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C17    -   C18    ...       1.38 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C8     ...       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C6     -   C7     ...       1.43 Ang.
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C28
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         23
            C2  -C1  -C8  -N2   -104.00 40.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         24
            C6  -C1  -C8  -N2     75.00 40.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         25
            C5  -C6  -C7  -N1     32.00 13.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         26
            C1  -C6  -C7  -N1   -147.00 13.00   1.555   1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      36.70 Deg.
              C25B -C24  -C25A    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      44.10 Deg.
              C26B -C24  -C26A    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      14.00 Deg.
              C23B -C21  -C23A    1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......       9.00 Deg.
              C27A -C17  -C27B    1.555   1.555   1.555

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

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

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997).

4,5-Bis(5-isopropyl-2-methylphenoxy)phthalonitrile

Crystal data

C28H26N2O2	F(000) = 904
Mr = 424.52	Dx = 1.134 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 13663 reflections
a = 15.5339 (13) Å	θ = 1.4–26.4°
b = 11.1141 (7) Å	µ = 0.07 mm^−1
c = 15.7665 (15) Å	T = 293 K
β = 114.061 (7)°	Prism, colourless
V = 2485.5 (4) Å^3	0.72 × 0.45 × 0.24 mm
Z = 4

Data collection

Stoe IPDS-2 diffractometer	4891 independent reflections
Radiation source: fine-focus sealed tube	2849 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.4°
w scans	h = −19→19
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→13
Tmin = 0.957, Tmax = 0.984	l = −19→19
34735 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.167	w = 1/[σ^2(Fo^2) + (0.1056P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.94	(Δ/σ)max = 0.026
4891 reflections	Δρmax = 0.37 e Å^−3
321 parameters	Δρmin = −0.20 e Å^−3
5 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (2)

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	Occ. (<1)
O1	0.81759 (9)	0.40730 (13)	0.44599 (9)	0.0658 (4)
O2	0.79073 (10)	0.64020 (12)	0.39861 (11)	0.0718 (4)
N2	1.09554 (16)	0.6728 (2)	0.26768 (18)	0.0998 (7)
N1	1.12645 (14)	0.32261 (19)	0.33368 (15)	0.0873 (6)
C28	0.68860 (18)	0.7072 (3)	0.20767 (19)	0.0977 (8)
H28A	0.6568	0.7487	0.1498	0.147*
H28B	0.6450	0.6549	0.2186	0.147*
H28C	0.7395	0.6605	0.2051	0.147*
C24	0.8246 (3)	1.0605 (3)	0.5083 (3)	0.1158 (10)
C21	0.5609 (2)	0.2956 (4)	0.1453 (2)	0.1364 (4)
C22	0.5022 (4)	0.1814 (4)	0.1259 (3)	0.1670 (18)
H22A	0.4816	0.1600	0.0616	0.251*
H22B	0.4483	0.1946	0.1398	0.251*
H22C	0.5396	0.1172	0.1639	0.251*
C23A	0.5024 (10)	0.3941 (9)	0.0786 (10)	0.219 (4)	0.668 (17)
H23A	0.4810	0.3659	0.0158	0.329*	0.668 (17)
H23B	0.5406	0.4646	0.0863	0.329*	0.668 (17)
H23C	0.4490	0.4135	0.0920	0.329*	0.668 (17)
C25A	0.9258 (8)	1.0462 (13)	0.5747 (8)	0.197 (5)	0.668 (17)
H25A	0.9420	1.1074	0.6216	0.295*	0.668 (17)
H25B	0.9654	1.0536	0.5416	0.295*	0.668 (17)
H25C	0.9347	0.9683	0.6034	0.295*	0.668 (17)
C26A	0.7847 (10)	1.0381 (11)	0.5805 (8)	0.158 (5)	0.668 (17)
H26A	0.8069	1.0993	0.6274	0.236*	0.668 (17)
H26B	0.8049	0.9607	0.6085	0.236*	0.668 (17)
H26C	0.7171	1.0403	0.5510	0.236*	0.668 (17)
C27A	0.6977 (7)	0.4487 (12)	0.5326 (8)	0.109 (3)	0.668 (17)
H27A	0.6469	0.4501	0.5525	0.164*	0.668 (17)
H27B	0.7226	0.5284	0.5359	0.164*	0.668 (17)
H27C	0.7465	0.3961	0.5723	0.164*	0.668 (17)
C23B	0.498 (3)	0.387 (3)	0.101 (2)	0.42 (4)	0.332 (17)
H23D	0.4706	0.3728	0.0351	0.635*	0.332 (17)
H23E	0.5309	0.4628	0.1133	0.635*	0.332 (17)
H23F	0.4492	0.3897	0.1234	0.635*	0.332 (17)
C25B	0.909 (2)	1.100 (2)	0.528 (2)	0.240 (18)	0.332 (17)
H25D	0.9309	1.0694	0.4835	0.360*	0.332 (17)
H25E	0.9501	1.0735	0.5891	0.360*	0.332 (17)
H25F	0.9080	1.1863	0.5260	0.360*	0.332 (17)
C26B	0.7451 (10)	1.0984 (16)	0.5220 (17)	0.140 (7)	0.332 (17)
H26D	0.6896	1.0629	0.4755	0.210*	0.332 (17)
H26E	0.7403	1.1844	0.5173	0.210*	0.332 (17)
H26F	0.7511	1.0738	0.5825	0.210*	0.332 (17)
C27B	0.696 (2)	0.430 (4)	0.537 (2)	0.209 (17)	0.332 (17)
H27D	0.6434	0.4353	0.5539	0.314*	0.332 (17)
H27E	0.7301	0.5048	0.5515	0.314*	0.332 (17)
H27F	0.7373	0.3664	0.5722	0.314*	0.332 (17)
C2	0.91900 (13)	0.63798 (18)	0.34833 (14)	0.0607 (5)
H2	0.9118	0.7194	0.3334	0.073*
C5	0.94100 (13)	0.39534 (18)	0.39414 (13)	0.0592 (5)
H5	0.9486	0.3143	0.4102	0.071*
C3	0.86042 (12)	0.58272 (17)	0.38317 (13)	0.0568 (5)
C6	0.99992 (13)	0.44912 (17)	0.35877 (13)	0.0568 (5)
C1	0.98854 (12)	0.57162 (18)	0.33572 (13)	0.0582 (5)
C4	0.87170 (12)	0.46044 (17)	0.40571 (12)	0.0551 (5)
C9	0.77602 (14)	0.76342 (19)	0.37567 (15)	0.0652 (5)
C8	1.04840 (15)	0.62824 (19)	0.29801 (16)	0.0703 (6)
C7	1.07093 (14)	0.37947 (18)	0.34496 (15)	0.0655 (5)
C16	0.69047 (15)	0.3570 (2)	0.29943 (15)	0.0713 (6)
H16	0.7333	0.3486	0.2724	0.086*
C15	0.72186 (13)	0.39100 (17)	0.39032 (14)	0.0596 (5)
C10	0.72664 (14)	0.7964 (2)	0.28442 (16)	0.0721 (6)
C14	0.80866 (16)	0.8440 (2)	0.44873 (17)	0.0749 (6)
H14	0.8407	0.8163	0.5092	0.090*
C20	0.59594 (17)	0.3347 (2)	0.24701 (17)	0.0842 (7)
C13	0.79342 (19)	0.9667 (2)	0.43145 (19)	0.0846 (7)
C17	0.66186 (16)	0.4041 (2)	0.43454 (17)	0.0835 (7)
C11	0.71443 (18)	0.9195 (3)	0.2686 (2)	0.0918 (8)
H11	0.6834	0.9474	0.2081	0.110*
C12	0.7474 (2)	1.0017 (2)	0.3409 (2)	0.0983 (8)
H12	0.7379	1.0833	0.3274	0.118*
C18	0.56833 (18)	0.3796 (3)	0.3816 (2)	0.1140 (11)
H18	0.5256	0.3862	0.4090	0.137*
C19	0.53539 (18)	0.3456 (3)	0.2895 (2)	0.1039 (9)
H19	0.4715	0.3300	0.2562	0.125*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0543 (7)	0.0761 (9)	0.0666 (8)	−0.0078 (6)	0.0243 (7)	0.0098 (7)
O2	0.0713 (9)	0.0653 (8)	0.0960 (10)	0.0055 (7)	0.0517 (8)	0.0056 (7)
N2	0.0873 (14)	0.0977 (15)	0.1400 (19)	0.0141 (11)	0.0726 (15)	0.0360 (14)
N1	0.0739 (12)	0.0855 (14)	0.1108 (16)	0.0088 (10)	0.0461 (12)	−0.0088 (11)
C28	0.0670 (14)	0.134 (2)	0.0895 (17)	0.0037 (14)	0.0293 (13)	−0.0142 (16)
C24	0.138 (3)	0.0871 (19)	0.132 (3)	−0.004 (2)	0.065 (2)	−0.0241 (18)
C21	0.101	0.205	0.094	−0.0598 (19)	0.0301 (13)	−0.023 (2)
C22	0.159 (4)	0.185 (4)	0.151 (3)	−0.058 (3)	0.056 (3)	−0.074 (3)
C23A	0.345	0.166 (7)	0.077 (7)	−0.065 (7)	0.014 (6)	0.021
C25A	0.171 (7)	0.208 (11)	0.155 (7)	0.029 (7)	0.010 (6)	−0.099 (7)
C26A	0.211 (11)	0.160 (7)	0.150 (7)	−0.067 (7)	0.123 (8)	−0.063 (6)
C27A	0.079 (5)	0.183 (7)	0.077 (5)	−0.007 (5)	0.044 (4)	−0.029 (4)
C23B	0.76 (8)	0.36 (5)	0.057 (11)	−0.10 (4)	0.07 (2)	0.038
C25B	0.26 (3)	0.18 (2)	0.38 (4)	−0.18 (2)	0.24 (3)	−0.17 (2)
C26B	0.150 (10)	0.112 (10)	0.153 (15)	0.028 (8)	0.057 (10)	−0.047 (10)
C27B	0.134 (19)	0.39 (4)	0.14 (2)	−0.14 (2)	0.082 (16)	−0.10 (2)
C2	0.0580 (11)	0.0575 (11)	0.0711 (12)	0.0006 (8)	0.0309 (10)	0.0056 (9)
C5	0.0561 (10)	0.0552 (11)	0.0625 (11)	−0.0020 (8)	0.0203 (9)	0.0010 (9)
C3	0.0508 (10)	0.0603 (11)	0.0619 (11)	−0.0013 (8)	0.0255 (9)	−0.0025 (9)
C6	0.0488 (9)	0.0603 (11)	0.0587 (11)	−0.0004 (8)	0.0192 (8)	−0.0017 (9)
C1	0.0496 (10)	0.0669 (12)	0.0598 (11)	−0.0016 (8)	0.0241 (9)	0.0019 (9)
C4	0.0481 (10)	0.0612 (11)	0.0551 (10)	−0.0075 (8)	0.0201 (8)	0.0007 (8)
C9	0.0598 (11)	0.0661 (12)	0.0798 (14)	0.0090 (9)	0.0389 (11)	0.0081 (11)
C8	0.0618 (12)	0.0717 (13)	0.0843 (14)	0.0077 (10)	0.0368 (11)	0.0136 (11)
C7	0.0576 (11)	0.0655 (12)	0.0736 (13)	−0.0021 (10)	0.0269 (10)	−0.0028 (10)
C16	0.0619 (12)	0.0854 (14)	0.0741 (14)	−0.0132 (10)	0.0353 (11)	−0.0076 (11)
C15	0.0508 (10)	0.0581 (11)	0.0720 (13)	−0.0053 (8)	0.0272 (9)	0.0037 (9)
C10	0.0549 (11)	0.0901 (16)	0.0785 (15)	0.0106 (11)	0.0345 (11)	0.0036 (12)
C14	0.0798 (14)	0.0743 (14)	0.0769 (14)	0.0094 (11)	0.0384 (12)	0.0050 (12)
C20	0.0648 (13)	0.1118 (19)	0.0769 (15)	−0.0206 (12)	0.0297 (12)	−0.0113 (13)
C13	0.0942 (17)	0.0693 (15)	0.0997 (19)	0.0069 (12)	0.0491 (15)	0.0004 (13)
C17	0.0656 (13)	0.1120 (18)	0.0805 (15)	−0.0104 (12)	0.0376 (12)	−0.0135 (13)
C11	0.0833 (16)	0.107 (2)	0.0905 (17)	0.0273 (15)	0.0405 (14)	0.0287 (16)
C12	0.110 (2)	0.0741 (16)	0.122 (2)	0.0224 (14)	0.0584 (19)	0.0221 (16)
C18	0.0629 (15)	0.190 (3)	0.101 (2)	−0.0180 (17)	0.0462 (15)	−0.031 (2)
C19	0.0568 (13)	0.161 (3)	0.0933 (19)	−0.0209 (15)	0.0302 (13)	−0.0207 (18)

Geometric parameters (Å, º)

O1—C4	1.376 (2)	C25B—H25D	0.9600
O1—C15	1.397 (2)	C25B—H25E	0.9600
O2—C3	1.362 (2)	C25B—H25F	0.9600
O2—C9	1.411 (2)	C26B—H26D	0.9600
N2—C8	1.138 (3)	C26B—H26E	0.9600
N1—C7	1.140 (3)	C26B—H26F	0.9600
C28—C10	1.487 (3)	C27B—C17	1.51 (3)
C28—H28A	0.9600	C27B—H27D	0.9600
C28—H28B	0.9600	C27B—H27E	0.9600
C28—H28C	0.9600	C27B—H27F	0.9600
C24—C25B	1.292 (18)	C2—C3	1.384 (3)
C24—C26B	1.401 (15)	C2—C1	1.388 (3)
C24—C25A	1.500 (11)	C2—H2	0.9300
C24—C13	1.520 (4)	C5—C4	1.370 (3)
C24—C26A	1.521 (7)	C5—C6	1.386 (3)
C21—C23B	1.388 (19)	C5—H5	0.9300
C21—C22	1.520 (5)	C3—C4	1.398 (3)
C21—C20	1.532 (4)	C6—C1	1.402 (3)
C21—C23A	1.534 (11)	C6—C7	1.435 (3)
C22—H22A	0.9600	C1—C8	1.437 (3)
C22—H22B	0.9600	C9—C10	1.376 (3)
C22—H22C	0.9600	C9—C14	1.382 (3)
C23A—H23A	0.9600	C16—C15	1.366 (3)
C23A—H23B	0.9600	C16—C20	1.382 (3)
C23A—H23C	0.9600	C16—H16	0.9300
C25A—H25A	0.9600	C15—C17	1.380 (3)
C25A—H25B	0.9600	C10—C11	1.390 (3)
C25A—H25C	0.9600	C14—C13	1.392 (3)
C26A—H26A	0.9600	C14—H14	0.9300
C26A—H26B	0.9600	C20—C19	1.364 (3)
C26A—H26C	0.9600	C13—C12	1.367 (4)
C27A—C17	1.498 (11)	C17—C18	1.376 (4)
C27A—H27A	0.9600	C11—C12	1.385 (4)
C27A—H27B	0.9600	C11—H11	0.9300
C27A—H27C	0.9600	C12—H12	0.9300
C23B—H23D	0.9600	C18—C19	1.382 (4)
C23B—H23E	0.9600	C18—H18	0.9300
C23B—H23F	0.9600	C19—H19	0.9300
C4—O1—C15	117.38 (14)	C24—C26B—H26F	109.5
C3—O2—C9	117.84 (14)	H26D—C26B—H26F	109.5
C10—C28—H28A	109.5	H26E—C26B—H26F	109.5
C10—C28—H28B	109.5	C17—C27B—H27D	109.5
H28A—C28—H28B	109.5	C17—C27B—H27E	109.5
C10—C28—H28C	109.5	H27D—C27B—H27E	109.5
H28A—C28—H28C	109.5	C17—C27B—H27F	109.5
H28B—C28—H28C	109.5	H27D—C27B—H27F	109.5
C25B—C24—C26B	136.9 (12)	H27E—C27B—H27F	109.5
C25B—C24—C25A	36.7 (15)	C3—C2—C1	119.83 (18)
C26B—C24—C25A	131.5 (11)	C3—C2—H2	120.1
C25B—C24—C13	112.7 (11)	C1—C2—H2	120.1
C26B—C24—C13	108.3 (6)	C4—C5—C6	120.63 (18)
C25A—C24—C13	112.7 (5)	C4—C5—H5	119.7
C25B—C24—C26A	123.9 (17)	C6—C5—H5	119.7
C26B—C24—C26A	44.1 (7)	O2—C3—C2	124.21 (17)
C25A—C24—C26A	95.2 (10)	O2—C3—C4	115.92 (16)
C13—C24—C26A	113.0 (4)	C2—C3—C4	119.87 (17)
C23B—C21—C22	106 (2)	C5—C6—C1	119.26 (17)
C23B—C21—C20	101.3 (16)	C5—C6—C7	120.19 (18)
C22—C21—C20	112.1 (3)	C1—C6—C7	120.54 (17)
C23B—C21—C23A	14 (2)	C2—C1—C6	120.16 (17)
C22—C21—C23A	108.6 (6)	C2—C1—C8	119.96 (18)
C20—C21—C23A	111.9 (6)	C6—C1—C8	119.87 (17)
C21—C22—H22A	109.5	C5—C4—O1	119.73 (17)
C21—C22—H22B	109.5	C5—C4—C3	120.25 (16)
H22A—C22—H22B	109.5	O1—C4—C3	119.86 (16)
C21—C22—H22C	109.5	C10—C9—C14	123.9 (2)
H22A—C22—H22C	109.5	C10—C9—O2	119.3 (2)
H22B—C22—H22C	109.5	C14—C9—O2	116.69 (19)
C21—C23A—H23A	109.5	N2—C8—C1	179.6 (3)
C21—C23A—H23B	109.5	N1—C7—C6	178.9 (2)
H23A—C23A—H23B	109.5	C15—C16—C20	121.0 (2)
C21—C23A—H23C	109.5	C15—C16—H16	119.5
H23A—C23A—H23C	109.5	C20—C16—H16	119.5
H23B—C23A—H23C	109.5	C16—C15—C17	122.24 (19)
C24—C25A—H25A	109.5	C16—C15—O1	121.91 (17)
C24—C25A—H25B	109.5	C17—C15—O1	115.73 (18)
H25A—C25A—H25B	109.5	C9—C10—C11	115.2 (2)
C24—C25A—H25C	109.5	C9—C10—C28	122.7 (2)
H25A—C25A—H25C	109.5	C11—C10—C28	122.0 (2)
H25B—C25A—H25C	109.5	C9—C14—C13	119.8 (2)
C24—C26A—H26A	109.5	C9—C14—H14	120.1
C24—C26A—H26B	109.5	C13—C14—H14	120.1
H26A—C26A—H26B	109.5	C19—C20—C16	117.9 (2)
C24—C26A—H26C	109.5	C19—C20—C21	121.2 (2)
H26A—C26A—H26C	109.5	C16—C20—C21	120.9 (2)
H26B—C26A—H26C	109.5	C12—C13—C14	117.2 (2)
C17—C27A—H27A	109.5	C12—C13—C24	119.9 (3)
C17—C27A—H27B	109.5	C14—C13—C24	122.8 (3)
H27A—C27A—H27B	109.5	C18—C17—C15	115.9 (2)
C17—C27A—H27C	109.5	C18—C17—C27A	123.2 (4)
H27A—C27A—H27C	109.5	C15—C17—C27A	120.8 (4)
H27B—C27A—H27C	109.5	C18—C17—C27B	120.8 (11)
C21—C23B—H23D	109.5	C15—C17—C27B	123.0 (11)
C21—C23B—H23E	109.4	C27A—C17—C27B	9 (2)
H23D—C23B—H23E	109.5	C12—C11—C10	121.6 (2)
C21—C23B—H23F	109.5	C12—C11—H11	119.2
H23D—C23B—H23F	109.5	C10—C11—H11	119.2
H23E—C23B—H23F	109.5	C13—C12—C11	122.2 (2)
C24—C25B—H25D	109.5	C13—C12—H12	118.9
C24—C25B—H25E	109.5	C11—C12—H12	118.9
H25D—C25B—H25E	109.5	C17—C18—C19	122.6 (2)
C24—C25B—H25F	109.5	C17—C18—H18	118.7
H25D—C25B—H25F	109.5	C19—C18—H18	118.7
H25E—C25B—H25F	109.5	C20—C19—C18	120.4 (2)
C24—C26B—H26D	109.5	C20—C19—H19	119.8
C24—C26B—H26E	109.5	C18—C19—H19	119.8
H26D—C26B—H26E	109.5
C9—O2—C3—C2	1.4 (3)	C15—C16—C20—C19	−1.2 (4)
C9—O2—C3—C4	−179.17 (17)	C15—C16—C20—C21	−179.5 (3)
C1—C2—C3—O2	179.52 (17)	C23B—C21—C20—C19	61 (2)
C1—C2—C3—C4	0.2 (3)	C22—C21—C20—C19	−51.0 (5)
C4—C5—C6—C1	0.6 (3)	C23A—C21—C20—C19	71.3 (8)
C4—C5—C6—C7	−178.60 (17)	C23B—C21—C20—C16	−121 (2)
C3—C2—C1—C6	−0.4 (3)	C22—C21—C20—C16	127.2 (4)
C3—C2—C1—C8	178.90 (18)	C23A—C21—C20—C16	−110.5 (7)
C5—C6—C1—C2	0.0 (3)	C9—C14—C13—C12	−1.1 (4)
C7—C6—C1—C2	179.28 (18)	C9—C14—C13—C24	178.1 (2)
C5—C6—C1—C8	−179.30 (18)	C25B—C24—C13—C12	−90.6 (18)
C7—C6—C1—C8	−0.1 (3)	C26B—C24—C13—C12	75.9 (12)
C6—C5—C4—O1	−176.18 (16)	C25A—C24—C13—C12	−130.5 (7)
C6—C5—C4—C3	−0.9 (3)	C26A—C24—C13—C12	122.9 (8)
C15—O1—C4—C5	−113.95 (19)	C25B—C24—C13—C14	90.1 (18)
C15—O1—C4—C3	70.8 (2)	C26B—C24—C13—C14	−103.3 (12)
O2—C3—C4—C5	−178.89 (17)	C25A—C24—C13—C14	50.2 (8)
C2—C3—C4—C5	0.5 (3)	C26A—C24—C13—C14	−56.3 (8)
O2—C3—C4—O1	−3.6 (2)	C16—C15—C17—C18	0.6 (4)
C2—C3—C4—O1	175.77 (17)	O1—C15—C17—C18	−175.5 (2)
C3—O2—C9—C10	79.1 (2)	C16—C15—C17—C27A	−176.3 (6)
C3—O2—C9—C14	−104.3 (2)	O1—C15—C17—C27A	7.7 (7)
C2—C1—C8—N2	−104 (40)	C16—C15—C17—C27B	174 (2)
C6—C1—C8—N2	75 (40)	O1—C15—C17—C27B	−2 (2)
C5—C6—C7—N1	32 (13)	C9—C10—C11—C12	−2.1 (3)
C1—C6—C7—N1	−147 (13)	C28—C10—C11—C12	177.8 (2)
C20—C16—C15—C17	0.5 (4)	C14—C13—C12—C11	1.8 (4)
C20—C16—C15—O1	176.3 (2)	C24—C13—C12—C11	−177.5 (3)
C4—O1—C15—C16	39.1 (3)	C10—C11—C12—C13	−0.1 (4)
C4—O1—C15—C17	−144.78 (19)	C15—C17—C18—C19	−0.9 (5)
C14—C9—C10—C11	2.7 (3)	C27A—C17—C18—C19	175.9 (7)
O2—C9—C10—C11	179.06 (17)	C27B—C17—C18—C19	−174 (2)
C14—C9—C10—C28	−177.1 (2)	C16—C20—C19—C18	1.0 (5)
O2—C9—C10—C28	−0.8 (3)	C21—C20—C19—C18	179.2 (4)
C10—C9—C14—C13	−1.2 (3)	C17—C18—C19—C20	0.1 (6)
O2—C9—C14—C13	−177.60 (19)