4-(2-Methoxy-1-naphthyl­methoxy)­phthalo­nitrile

The title compound, C₂₀H₁₄N₂O₂, crystallizes in the centrosymmetric space group P2₁/c with two mol­ecules in the asymmetric unit. Both independent mol­ecules have the same geometry.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.087
• Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         34 Perc.
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C1B    -   C8B      =       9.06 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C2B    -   C3B      =       8.97 su

Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.680
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.101
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.10
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1A    -   C8A      =       6.89 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2A    -   C3A      =       6.82 su
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1A    -   C8A      =       1.44 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2A    -   C3A      =       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1B    -   C8B      =       1.43 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2B    -   C3B      =       1.44 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         27
            C7A -C8A -C1A -N1A  -144.00 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 ... #         28
            C3A -C8A -C1A -N1A    37.00 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 ... #         31
            C4A -C3A -C2A -N2A  -104.00 34.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         32
            C8A -C3A -C2A -N2A    76.00 34.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         74
            C7B -C8B -C1B -N1B   -18.00 17.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         75
            C3B -C8B -C1B -N1B   163.00100.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         90
            C4B -C3B -C2B -N2B   -14.00 15.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         91
            C8B -C3B -C2B -N2B   165.00100.00   1.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          4

   0 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

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

---

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; molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).

4-(2-Methoxy-1-naphthylmethoxy)phthalonitrile

Crystal data

C20H14N2O2	F(000) = 1312
Mr = 314.34	Dx = 1.298 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.1166 (9) Å	Cell parameters from 8964 reflections
b = 12.0736 (12) Å	θ = 1.6–22.9°
c = 20.9806 (15) Å	µ = 0.09 mm^−1
β = 104.454 (5)°	T = 293 K
V = 3217.4 (5) Å^3	Plate, yellow
Z = 8	0.30 × 0.23 × 0.12 mm

Data collection

Stoe IPDS-2 diffractometer	6304 independent reflections
Radiation source: fine-focus sealed tube	2114 reflections with I > 2σI)
Graphite monochromator	Rint = 0.101
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.6°
ω rotation scans	h = −15→16
Absorption correction: integration (X-RED; Stoe & Cie, 2002)	k = −14→14
Tmin = 0.976, Tmax = 0.990	l = −25→25
37155 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)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0334P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.68	(Δ/σ)max = 0.001
6304 reflections	Δρmax = 0.11 e Å^−3
436 parameters	Δρmin = −0.12 e Å^−3
0 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: 0.0031 (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
O2A	0.79217 (15)	0.60047 (15)	0.35243 (9)	0.1002 (6)
O2B	0.28933 (14)	0.49637 (15)	0.36589 (9)	0.0964 (6)
C20A	0.8122 (3)	0.6545 (3)	0.41376 (15)	0.1379 (13)
H20A	0.8184	0.6006	0.4481	0.207*
H20B	0.7553	0.7042	0.4144	0.207*
H20C	0.8766	0.6958	0.4206	0.207*
C20B	0.3034 (2)	0.5600 (2)	0.42438 (15)	0.1255 (11)
H20D	0.3287	0.5130	0.4619	0.188*
H20E	0.2373	0.5921	0.4264	0.188*
H20F	0.3536	0.6178	0.4243	0.188*
O1A	0.71751 (11)	0.54223 (12)	0.19595 (8)	0.0702 (4)
C4A	0.63498 (18)	0.63352 (18)	0.10015 (11)	0.0625 (6)
H4A	0.6985	0.6696	0.1024	0.075*
C5A	0.62727 (18)	0.55817 (18)	0.14823 (12)	0.0595 (6)
C6A	0.53261 (18)	0.50528 (18)	0.14552 (12)	0.0676 (6)
H6A	0.5267	0.4556	0.1783	0.081*
C8A	0.45350 (18)	0.60184 (19)	0.04519 (12)	0.0637 (6)
C9A	0.71283 (17)	0.46603 (19)	0.24807 (11)	0.0707 (7)
H9A1	0.6839	0.3958	0.2294	0.085*
H9A2	0.6672	0.4956	0.2739	0.085*
C7A	0.44716 (18)	0.52719 (19)	0.09353 (12)	0.0696 (7)
H7A	0.3839	0.4906	0.0912	0.083*
C10A	0.82130 (18)	0.4487 (2)	0.29133 (12)	0.0639 (6)
C3A	0.54940 (19)	0.65534 (17)	0.04914 (11)	0.0598 (6)
C14A	0.9852 (2)	0.3427 (2)	0.32354 (13)	0.0710 (7)
C15A	0.88563 (19)	0.35924 (19)	0.27935 (12)	0.0650 (6)
C1A	0.3634 (2)	0.6260 (2)	−0.00820 (15)	0.0791 (8)
C16A	0.8541 (2)	0.2850 (2)	0.22620 (13)	0.0796 (7)
H16A	0.7901	0.2959	0.1956	0.096*
C2A	0.55921 (19)	0.7335 (2)	−0.00033 (14)	0.0749 (7)
C12A	0.9584 (2)	0.5019 (2)	0.38668 (12)	0.0864 (8)
H12A	0.9827	0.5501	0.4217	0.104*
C11A	0.8581 (2)	0.5162 (2)	0.34407 (13)	0.0752 (7)
N1A	0.29324 (19)	0.6453 (2)	−0.05126 (13)	0.1109 (8)
N2A	0.56653 (19)	0.7966 (2)	−0.03955 (12)	0.1042 (8)
C18A	1.0129 (3)	0.1806 (2)	0.26351 (18)	0.1022 (10)
H18A	1.0542	0.1202	0.2584	0.123*
C17A	0.9155 (3)	0.1976 (2)	0.21893 (16)	0.0970 (9)
H17A	0.8926	0.1488	0.1840	0.116*
C13A	1.0191 (2)	0.4164 (2)	0.37576 (13)	0.0828 (8)
H13A	1.0854	0.4066	0.4040	0.099*
C19A	1.0470 (2)	0.2514 (3)	0.31384 (16)	0.0892 (8)
H19A	1.1124	0.2400	0.3428	0.107*
O1B	0.24615 (12)	0.44710 (13)	0.20037 (8)	0.0801 (5)
C10B	0.35431 (18)	0.37472 (19)	0.29918 (12)	0.0635 (6)
C5B	0.15199 (19)	0.4758 (2)	0.16018 (11)	0.0659 (6)
C3B	0.0655 (2)	0.60241 (19)	0.07626 (11)	0.0651 (6)
C14B	0.5394 (2)	0.31830 (19)	0.32883 (13)	0.0670 (6)
C6B	0.05794 (18)	0.42360 (19)	0.15835 (11)	0.0717 (7)
H6B	0.0554	0.3641	0.1860	0.086*
C15B	0.4382 (2)	0.31334 (18)	0.28512 (12)	0.0642 (6)
C4B	0.15612 (18)	0.5646 (2)	0.11894 (11)	0.0690 (7)
H4B	0.2202	0.5986	0.1202	0.083*
C7B	−0.03295 (19)	0.4613 (2)	0.11452 (12)	0.0730 (7)
H7B	−0.0967	0.4260	0.1126	0.088*
C8B	−0.03024 (19)	0.5500 (2)	0.07397 (11)	0.0669 (6)
C13B	0.5541 (2)	0.3862 (2)	0.38433 (13)	0.0766 (7)
H13B	0.6207	0.3907	0.4130	0.092*
C1B	−0.1257 (2)	0.5897 (2)	0.03059 (13)	0.0776 (7)
C12B	0.4743 (2)	0.4459 (2)	0.39766 (12)	0.0760 (7)
H12B	0.4861	0.4909	0.4348	0.091*
C9B	0.24603 (18)	0.37158 (19)	0.25419 (11)	0.0728 (7)
H9B1	0.2289	0.2971	0.2376	0.087*
H9B2	0.1943	0.3946	0.2775	0.087*
C11B	0.3733 (2)	0.43881 (19)	0.35466 (13)	0.0714 (6)
C16B	0.4258 (2)	0.2459 (2)	0.22859 (13)	0.0782 (7)
H16B	0.3604	0.2423	0.1985	0.094*
C2B	0.0708 (2)	0.6961 (2)	0.03488 (14)	0.0801 (8)
C19B	0.6223 (2)	0.2553 (2)	0.31557 (15)	0.0830 (8)
H19B	0.6887	0.2585	0.3444	0.100*
C18B	0.6065 (3)	0.1903 (2)	0.26153 (17)	0.0930 (9)
H18B	0.6617	0.1482	0.2539	0.112*
C17B	0.5078 (3)	0.1861 (2)	0.21721 (14)	0.0918 (8)
H17B	0.4978	0.1424	0.1797	0.110*
N1B	−0.20274 (19)	0.6199 (2)	−0.00397 (12)	0.1038 (8)
N2B	0.0767 (2)	0.7709 (2)	0.00272 (13)	0.1107 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2A	0.1071 (15)	0.1006 (14)	0.0838 (14)	0.0269 (12)	0.0070 (11)	−0.0155 (11)
O2B	0.0789 (12)	0.1067 (14)	0.0945 (14)	0.0170 (11)	0.0046 (11)	−0.0212 (11)
C20A	0.139 (3)	0.170 (3)	0.098 (2)	0.025 (2)	0.016 (2)	−0.054 (2)
C20B	0.113 (2)	0.134 (3)	0.125 (3)	0.012 (2)	0.020 (2)	−0.059 (2)
O1A	0.0603 (10)	0.0758 (10)	0.0689 (11)	−0.0078 (8)	0.0058 (9)	0.0159 (9)
C4A	0.0563 (16)	0.0660 (15)	0.0641 (16)	−0.0023 (12)	0.0128 (14)	0.0002 (13)
C5A	0.0538 (15)	0.0626 (15)	0.0590 (15)	0.0003 (13)	0.0082 (13)	−0.0009 (13)
C6A	0.0608 (16)	0.0670 (15)	0.0736 (17)	−0.0027 (13)	0.0142 (15)	0.0068 (13)
C8A	0.0553 (16)	0.0668 (16)	0.0631 (16)	0.0077 (13)	0.0039 (14)	−0.0084 (13)
C9A	0.0684 (17)	0.0737 (16)	0.0692 (17)	0.0021 (13)	0.0157 (14)	0.0179 (14)
C7A	0.0567 (16)	0.0706 (17)	0.0796 (18)	−0.0012 (13)	0.0137 (15)	−0.0094 (15)
C10A	0.0597 (16)	0.0673 (15)	0.0614 (16)	0.0016 (14)	0.0091 (13)	0.0116 (13)
C3A	0.0641 (17)	0.0590 (14)	0.0554 (15)	0.0080 (13)	0.0132 (14)	−0.0009 (12)
C14A	0.0628 (17)	0.0755 (18)	0.0733 (18)	0.0045 (15)	0.0142 (16)	0.0178 (15)
C15A	0.0671 (17)	0.0662 (16)	0.0623 (16)	−0.0041 (14)	0.0173 (14)	0.0131 (13)
C1A	0.0697 (18)	0.0760 (18)	0.0839 (19)	0.0019 (15)	0.0046 (17)	−0.0118 (15)
C16A	0.0728 (18)	0.0775 (18)	0.090 (2)	0.0001 (16)	0.0236 (16)	0.0004 (16)
C2A	0.0705 (18)	0.0797 (19)	0.0720 (19)	0.0134 (15)	0.0132 (15)	0.0040 (16)
C12A	0.087 (2)	0.092 (2)	0.0699 (19)	−0.0007 (17)	0.0016 (17)	0.0020 (15)
C11A	0.0775 (19)	0.0774 (19)	0.0663 (18)	0.0076 (15)	0.0093 (16)	0.0081 (15)
N1A	0.0827 (17)	0.1173 (19)	0.112 (2)	0.0042 (15)	−0.0144 (16)	0.0028 (16)
N2A	0.1044 (19)	0.1096 (19)	0.099 (2)	0.0213 (15)	0.0262 (16)	0.0297 (16)
C18A	0.108 (3)	0.083 (2)	0.129 (3)	0.015 (2)	0.054 (2)	0.017 (2)
C17A	0.099 (2)	0.087 (2)	0.110 (2)	−0.0026 (19)	0.036 (2)	−0.0098 (18)
C13A	0.0676 (18)	0.101 (2)	0.0723 (19)	0.0012 (17)	0.0026 (15)	0.0223 (17)
C19A	0.0735 (19)	0.095 (2)	0.102 (2)	0.0162 (19)	0.0283 (18)	0.0341 (19)
O1B	0.0620 (11)	0.0962 (12)	0.0734 (11)	−0.0102 (10)	0.0003 (10)	0.0165 (10)
C10B	0.0581 (16)	0.0656 (15)	0.0616 (16)	−0.0063 (13)	0.0051 (13)	0.0055 (13)
C5B	0.0576 (17)	0.0737 (17)	0.0604 (16)	−0.0033 (14)	0.0031 (14)	−0.0012 (13)
C3B	0.0712 (18)	0.0637 (16)	0.0610 (16)	0.0035 (14)	0.0176 (14)	−0.0018 (13)
C14B	0.0667 (18)	0.0596 (16)	0.0731 (18)	−0.0034 (14)	0.0141 (15)	0.0154 (14)
C6B	0.0651 (17)	0.0766 (17)	0.0686 (17)	−0.0094 (14)	0.0079 (15)	0.0038 (13)
C15B	0.0702 (18)	0.0605 (15)	0.0613 (17)	−0.0104 (13)	0.0156 (15)	0.0064 (13)
C4B	0.0629 (17)	0.0756 (17)	0.0650 (16)	−0.0080 (14)	0.0097 (14)	−0.0032 (14)
C7B	0.0626 (17)	0.0821 (18)	0.0696 (17)	−0.0070 (14)	0.0077 (14)	−0.0006 (15)
C8B	0.0617 (17)	0.0747 (16)	0.0592 (16)	0.0078 (15)	0.0056 (13)	−0.0041 (14)
C13B	0.0700 (18)	0.0758 (18)	0.0734 (18)	−0.0039 (15)	−0.0018 (15)	0.0101 (15)
C1B	0.0765 (19)	0.0866 (19)	0.0720 (19)	0.0047 (16)	0.0227 (17)	0.0011 (15)
C12B	0.0811 (19)	0.0681 (16)	0.0693 (17)	−0.0032 (15)	0.0011 (16)	−0.0022 (14)
C9B	0.0660 (17)	0.0772 (16)	0.0713 (17)	−0.0076 (13)	0.0101 (14)	0.0125 (14)
C11B	0.0689 (17)	0.0683 (16)	0.0721 (17)	0.0032 (14)	0.0084 (15)	0.0028 (14)
C16B	0.0821 (19)	0.0759 (17)	0.0755 (19)	−0.0105 (16)	0.0174 (15)	0.0012 (15)
C2B	0.0771 (19)	0.083 (2)	0.078 (2)	0.0080 (16)	0.0157 (16)	−0.0041 (17)
C19B	0.0756 (19)	0.0751 (18)	0.100 (2)	0.0042 (16)	0.0243 (17)	0.0237 (17)
C18B	0.100 (3)	0.081 (2)	0.108 (3)	0.0102 (18)	0.044 (2)	0.0180 (19)
C17B	0.113 (3)	0.082 (2)	0.085 (2)	−0.0041 (19)	0.035 (2)	−0.0025 (16)
N1B	0.0808 (17)	0.126 (2)	0.1017 (19)	0.0162 (15)	0.0169 (15)	0.0241 (16)
N2B	0.123 (2)	0.102 (2)	0.109 (2)	0.0062 (17)	0.0326 (17)	0.0214 (16)

Geometric parameters (Å, º)

O2A—C11A	1.375 (3)	C18A—C17A	1.397 (4)
O2A—C20A	1.408 (3)	C18A—H18A	0.9300
O2B—C11B	1.371 (3)	C17A—H17A	0.9300
O2B—C20B	1.420 (3)	C13A—H13A	0.9300
C20A—H20A	0.9600	C19A—H19A	0.9300
C20A—H20B	0.9600	O1B—C5B	1.355 (2)
C20A—H20C	0.9600	O1B—C9B	1.452 (2)
C20B—H20D	0.9600	C10B—C11B	1.368 (3)
C20B—H20E	0.9600	C10B—C15B	1.417 (3)
C20B—H20F	0.9600	C10B—C9B	1.497 (3)
O1A—C5A	1.360 (2)	C5B—C6B	1.377 (3)
O1A—C9A	1.442 (2)	C5B—C4B	1.387 (3)
C4A—C3A	1.369 (3)	C3B—C4B	1.376 (3)
C4A—C5A	1.381 (3)	C3B—C8B	1.396 (3)
C4A—H4A	0.9300	C3B—C2B	1.438 (3)
C5A—C6A	1.385 (3)	C14B—C13B	1.397 (3)
C6A—C7A	1.380 (3)	C14B—C19B	1.410 (3)
C6A—H6A	0.9300	C14B—C15B	1.414 (3)
C8A—C7A	1.375 (3)	C6B—C7B	1.388 (3)
C8A—C3A	1.398 (3)	C6B—H6B	0.9300
C8A—C1A	1.441 (3)	C15B—C16B	1.414 (3)
C9A—C10A	1.499 (3)	C4B—H4B	0.9300
C9A—H9A1	0.9700	C7B—C8B	1.374 (3)
C9A—H9A2	0.9700	C7B—H7B	0.9300
C7A—H7A	0.9300	C8B—C1B	1.434 (3)
C10A—C11A	1.362 (3)	C13B—C12B	1.357 (3)
C10A—C15A	1.431 (3)	C13B—H13B	0.9300
C3A—C2A	1.432 (3)	C1B—N1B	1.146 (3)
C14A—C13A	1.395 (3)	C12B—C11B	1.407 (3)
C14A—C19A	1.412 (3)	C12B—H12B	0.9300
C14A—C15A	1.414 (3)	C9B—H9B1	0.9700
C15A—C16A	1.410 (3)	C9B—H9B2	0.9700
C1A—N1A	1.141 (3)	C16B—C17B	1.365 (3)
C16A—C17A	1.359 (3)	C16B—H16B	0.9300
C16A—H16A	0.9300	C2B—N2B	1.141 (3)
C2A—N2A	1.143 (3)	C19B—C18B	1.352 (3)
C12A—C13A	1.358 (3)	C19B—H19B	0.9300
C12A—C11A	1.404 (3)	C18B—C17B	1.393 (4)
C12A—H12A	0.9300	C18B—H18B	0.9300
C18A—C19A	1.346 (4)	C17B—H17B	0.9300
C11A—O2A—C20A	118.7 (2)	C18A—C17A—H17A	119.7
C11B—O2B—C20B	119.1 (2)	C12A—C13A—C14A	122.1 (3)
O2A—C20A—H20A	109.5	C12A—C13A—H13A	118.9
O2A—C20A—H20B	109.5	C14A—C13A—H13A	118.9
H20A—C20A—H20B	109.5	C18A—C19A—C14A	121.3 (3)
O2A—C20A—H20C	109.5	C18A—C19A—H19A	119.4
H20A—C20A—H20C	109.5	C14A—C19A—H19A	119.4
H20B—C20A—H20C	109.5	C5B—O1B—C9B	117.81 (18)
O2B—C20B—H20D	109.5	C11B—C10B—C15B	119.2 (2)
O2B—C20B—H20E	109.5	C11B—C10B—C9B	119.6 (2)
H20D—C20B—H20E	109.5	C15B—C10B—C9B	121.3 (2)
O2B—C20B—H20F	109.5	O1B—C5B—C6B	124.9 (2)
H20D—C20B—H20F	109.5	O1B—C5B—C4B	114.5 (2)
H20E—C20B—H20F	109.5	C6B—C5B—C4B	120.7 (2)
C5A—O1A—C9A	117.04 (17)	C4B—C3B—C8B	119.7 (2)
C3A—C4A—C5A	120.2 (2)	C4B—C3B—C2B	119.3 (2)
C3A—C4A—H4A	119.9	C8B—C3B—C2B	121.0 (2)
C5A—C4A—H4A	119.9	C13B—C14B—C19B	121.9 (3)
O1A—C5A—C4A	115.0 (2)	C13B—C14B—C15B	118.5 (2)
O1A—C5A—C6A	124.9 (2)	C19B—C14B—C15B	119.6 (3)
C4A—C5A—C6A	120.2 (2)	C5B—C6B—C7B	118.9 (2)
C7A—C6A—C5A	119.1 (2)	C5B—C6B—H6B	120.5
C7A—C6A—H6A	120.4	C7B—C6B—H6B	120.5
C5A—C6A—H6A	120.4	C16B—C15B—C14B	117.5 (2)
C7A—C8A—C3A	118.6 (2)	C16B—C15B—C10B	122.9 (2)
C7A—C8A—C1A	121.1 (2)	C14B—C15B—C10B	119.7 (2)
C3A—C8A—C1A	120.3 (2)	C3B—C4B—C5B	120.0 (2)
O1A—C9A—C10A	109.55 (18)	C3B—C4B—H4B	120.0
O1A—C9A—H9A1	109.8	C5B—C4B—H4B	120.0
C10A—C9A—H9A1	109.8	C8B—C7B—C6B	121.0 (2)
O1A—C9A—H9A2	109.8	C8B—C7B—H7B	119.5
C10A—C9A—H9A2	109.8	C6B—C7B—H7B	119.5
H9A1—C9A—H9A2	108.2	C7B—C8B—C3B	119.6 (2)
C8A—C7A—C6A	121.5 (2)	C7B—C8B—C1B	120.0 (2)
C8A—C7A—H7A	119.3	C3B—C8B—C1B	120.4 (2)
C6A—C7A—H7A	119.3	C12B—C13B—C14B	122.0 (2)
C11A—C10A—C15A	119.3 (2)	C12B—C13B—H13B	119.0
C11A—C10A—C9A	119.9 (2)	C14B—C13B—H13B	119.0
C15A—C10A—C9A	120.8 (2)	N1B—C1B—C8B	179.0 (3)
C4A—C3A—C8A	120.5 (2)	C13B—C12B—C11B	119.2 (2)
C4A—C3A—C2A	119.3 (2)	C13B—C12B—H12B	120.4
C8A—C3A—C2A	120.3 (2)	C11B—C12B—H12B	120.4
C13A—C14A—C19A	121.9 (3)	O1B—C9B—C10B	106.83 (18)
C13A—C14A—C15A	119.1 (2)	O1B—C9B—H9B1	110.4
C19A—C14A—C15A	119.0 (3)	C10B—C9B—H9B1	110.4
C16A—C15A—C14A	118.0 (2)	O1B—C9B—H9B2	110.4
C16A—C15A—C10A	123.3 (2)	C10B—C9B—H9B2	110.4
C14A—C15A—C10A	118.7 (2)	H9B1—C9B—H9B2	108.6
N1A—C1A—C8A	178.7 (3)	C10B—C11B—O2B	116.7 (2)
C17A—C16A—C15A	121.1 (3)	C10B—C11B—C12B	121.5 (2)
C17A—C16A—H16A	119.4	O2B—C11B—C12B	121.8 (2)
C15A—C16A—H16A	119.4	C17B—C16B—C15B	121.4 (3)
N2A—C2A—C3A	179.4 (3)	C17B—C16B—H16B	119.3
C13A—C12A—C11A	118.8 (3)	C15B—C16B—H16B	119.3
C13A—C12A—H12A	120.6	N2B—C2B—C3B	178.8 (3)
C11A—C12A—H12A	120.6	C18B—C19B—C14B	121.0 (3)
C10A—C11A—O2A	116.1 (2)	C18B—C19B—H19B	119.5
C10A—C11A—C12A	121.9 (3)	C14B—C19B—H19B	119.5
O2A—C11A—C12A	121.9 (3)	C19B—C18B—C17B	120.2 (3)
C19A—C18A—C17A	120.0 (3)	C19B—C18B—H18B	119.9
C19A—C18A—H18A	120.0	C17B—C18B—H18B	119.9
C17A—C18A—H18A	120.0	C16B—C17B—C18B	120.4 (3)
C16A—C17A—C18A	120.6 (3)	C16B—C17B—H17B	119.8
C16A—C17A—H17A	119.7	C18B—C17B—H17B	119.8
C9A—O1A—C5A—C4A	178.69 (18)	C9B—O1B—C5B—C6B	−13.0 (3)
C9A—O1A—C5A—C6A	−1.3 (3)	C9B—O1B—C5B—C4B	167.22 (19)
C3A—C4A—C5A—O1A	179.2 (2)	O1B—C5B—C6B—C7B	−179.8 (2)
C3A—C4A—C5A—C6A	−0.8 (3)	C4B—C5B—C6B—C7B	0.0 (3)
O1A—C5A—C6A—C7A	−178.7 (2)	C13B—C14B—C15B—C16B	178.7 (2)
C4A—C5A—C6A—C7A	1.4 (3)	C19B—C14B—C15B—C16B	−1.3 (3)
C5A—O1A—C9A—C10A	173.32 (19)	C13B—C14B—C15B—C10B	−1.4 (3)
C3A—C8A—C7A—C6A	0.6 (3)	C19B—C14B—C15B—C10B	178.58 (19)
C1A—C8A—C7A—C6A	−178.7 (2)	C11B—C10B—C15B—C16B	−179.4 (2)
C5A—C6A—C7A—C8A	−1.3 (3)	C9B—C10B—C15B—C16B	0.0 (3)
O1A—C9A—C10A—C11A	89.6 (2)	C11B—C10B—C15B—C14B	0.7 (3)
O1A—C9A—C10A—C15A	−92.7 (2)	C9B—C10B—C15B—C14B	−179.9 (2)
C5A—C4A—C3A—C8A	0.1 (3)	C8B—C3B—C4B—C5B	−0.9 (3)
C5A—C4A—C3A—C2A	−179.8 (2)	C2B—C3B—C4B—C5B	178.6 (2)
C7A—C8A—C3A—C4A	0.0 (3)	O1B—C5B—C4B—C3B	−179.3 (2)
C1A—C8A—C3A—C4A	179.3 (2)	C6B—C5B—C4B—C3B	0.9 (3)
C7A—C8A—C3A—C2A	179.9 (2)	C5B—C6B—C7B—C8B	−0.8 (4)
C1A—C8A—C3A—C2A	−0.8 (3)	C6B—C7B—C8B—C3B	0.7 (3)
C13A—C14A—C15A—C16A	178.7 (2)	C6B—C7B—C8B—C1B	−178.0 (2)
C19A—C14A—C15A—C16A	−1.9 (3)	C4B—C3B—C8B—C7B	0.2 (3)
C13A—C14A—C15A—C10A	−2.5 (3)	C2B—C3B—C8B—C7B	−179.4 (2)
C19A—C14A—C15A—C10A	177.0 (2)	C4B—C3B—C8B—C1B	178.9 (2)
C11A—C10A—C15A—C16A	179.8 (2)	C2B—C3B—C8B—C1B	−0.7 (3)
C9A—C10A—C15A—C16A	2.1 (3)	C19B—C14B—C13B—C12B	−179.1 (2)
C11A—C10A—C15A—C14A	1.0 (3)	C15B—C14B—C13B—C12B	0.8 (3)
C9A—C10A—C15A—C14A	−176.7 (2)	C7B—C8B—C1B—N1B	−18 (17)
C7A—C8A—C1A—N1A	−144 (13)	C3B—C8B—C1B—N1B	163 (100)
C3A—C8A—C1A—N1A	37 (13)	C14B—C13B—C12B—C11B	0.4 (4)
C14A—C15A—C16A—C17A	2.4 (3)	C5B—O1B—C9B—C10B	−167.0 (2)
C10A—C15A—C16A—C17A	−176.4 (2)	C11B—C10B—C9B—O1B	98.9 (2)
C4A—C3A—C2A—N2A	−104 (34)	C15B—C10B—C9B—O1B	−80.5 (2)
C8A—C3A—C2A—N2A	76 (34)	C15B—C10B—C11B—O2B	−179.96 (19)
C15A—C10A—C11A—O2A	179.86 (19)	C9B—C10B—C11B—O2B	0.7 (3)
C9A—C10A—C11A—O2A	−2.4 (3)	C15B—C10B—C11B—C12B	0.6 (3)
C15A—C10A—C11A—C12A	1.1 (3)	C9B—C10B—C11B—C12B	−178.8 (2)
C9A—C10A—C11A—C12A	178.8 (2)	C20B—O2B—C11B—C10B	177.0 (2)
C20A—O2A—C11A—C10A	163.7 (2)	C20B—O2B—C11B—C12B	−3.5 (4)
C20A—O2A—C11A—C12A	−17.5 (4)	C13B—C12B—C11B—C10B	−1.2 (4)
C13A—C12A—C11A—C10A	−1.7 (4)	C13B—C12B—C11B—O2B	179.4 (2)
C13A—C12A—C11A—O2A	179.6 (2)	C14B—C15B—C16B—C17B	1.3 (3)
C15A—C16A—C17A—C18A	−1.2 (4)	C10B—C15B—C16B—C17B	−178.7 (2)
C19A—C18A—C17A—C16A	−0.6 (4)	C4B—C3B—C2B—N2B	−14 (15)
C11A—C12A—C13A—C14A	0.2 (4)	C8B—C3B—C2B—N2B	165 (100)
C19A—C14A—C13A—C12A	−177.5 (2)	C13B—C14B—C19B—C18B	−179.8 (2)
C15A—C14A—C13A—C12A	1.8 (4)	C15B—C14B—C19B—C18B	0.2 (3)
C17A—C18A—C19A—C14A	1.1 (4)	C14B—C19B—C18B—C17B	1.2 (4)
C13A—C14A—C19A—C18A	179.5 (2)	C15B—C16B—C17B—C18B	0.0 (4)
C15A—C14A—C19A—C18A	0.1 (4)	C19B—C18B—C17B—C16B	−1.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9A—H9A2···O2A	0.97	2.38	2.716 (3)	100
C9B—H9B2···O2B	0.97	2.31	2.724 (3)	105