Inclusion compounds of binaphthol with picolines: structures, selectivity and kinetics of desolvation

The crystal structures of the inclusion compounds formed between the host 2,2'-dihydroxy-1,1'-binaphthyl and the three picoline isomers have been elucidated and their lattice energies calculated. The selectivities of enclathration by the host have been measured by competition experiments. The thermal stabilities and activation energies of desolvation of the compounds have been determined. The kinetics of desolvation are correlated to the structures.

Computing details

For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

Figures

(BNP2P)

Crystal data

C32H28N2O2	Z = 4
Mr = 472.56	F(000) = 1000
Monoclinic, C2/c	Dx = 1.239 Mg m^−3
a = 18.274 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.887 (2) Å	µ = 0.08 mm^−1
c = 14.021 (2) Å	T = 173 K
β = 90.41 (3)°	0.20 × 0.10 × 0.05 mm
V = 2533.2 (8) Å^3

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 26.4°, θmin = 2.2°
4593 measured reflections	h = −22→21
2461 independent reflections	k = −12→0
1727 reflections with I > 2σ(I)	l = −17→17

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)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0531P)^2 + 0.641P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2461 reflections	Δρmax = 0.17 e Å^−3
165 parameters	Δρmin = −0.17 e Å^−3
2 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0035 (6)

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	0.02757 (5)	0.19386 (10)	0.61837 (7)	0.0382 (3)
C1	0.04057 (7)	0.34995 (13)	0.74417 (9)	0.0254 (3)
C2	0.07191 (7)	0.26884 (14)	0.67643 (9)	0.0282 (3)
C3	0.14899 (7)	0.26451 (15)	0.66540 (10)	0.0319 (4)
H3	0.1698	0.2083	0.6178	0.038*
C4	0.19328 (7)	0.34037 (15)	0.72257 (10)	0.0324 (4)
H4	0.2448	0.3353	0.7152	0.039*
N1G	0.09256 (6)	−0.04505 (12)	0.58095 (8)	0.0354 (3)
C5	0.20801 (8)	0.50803 (15)	0.85267 (10)	0.0365 (4)
H5	0.2596	0.5060	0.8455	0.044*
C6	0.17817 (8)	0.58921 (17)	0.92039 (11)	0.0416 (4)
H6	0.2089	0.6432	0.9598	0.050*
C7	0.10174 (8)	0.59327 (15)	0.93217 (10)	0.0385 (4)
H7	0.0811	0.6499	0.9797	0.046*
C8	0.05718 (8)	0.51621 (15)	0.87568 (10)	0.0318 (4)
H8	0.0057	0.5199	0.8846	0.038*
C9	0.08605 (7)	0.43092 (13)	0.80409 (9)	0.0263 (3)
C10	0.16362 (7)	0.42664 (14)	0.79280 (9)	0.0286 (3)
C2G	0.12448 (7)	−0.10996 (16)	0.50886 (10)	0.0351 (4)
C6G	0.08514 (8)	−0.11094 (18)	0.66375 (11)	0.0432 (4)
H6G	0.0625	−0.0646	0.7150	0.052*
C4G	0.14044 (10)	−0.30715 (18)	0.60513 (13)	0.0558 (5)
H4G	0.1568	−0.3977	0.6129	0.067*
C3G	0.14901 (9)	−0.24201 (17)	0.51964 (12)	0.0491 (5)
H3G	0.1717	−0.2871	0.4678	0.059*
C1G	0.13261 (10)	−0.0348 (2)	0.41716 (11)	0.0574 (5)
H1G1	0.1119	0.0561	0.4238	0.086*	0.50
H1G3	0.1066	−0.0833	0.3662	0.086*	0.50
H1G5	0.1846	−0.0279	0.4012	0.086*	0.50
H1G4	0.1568	−0.0929	0.3704	0.086*	0.50
H1G6	0.1622	0.0466	0.4280	0.086*	0.50
H1G2	0.0842	−0.0088	0.3930	0.086*	0.50
C5G	0.10813 (9)	−0.24044 (18)	0.67904 (12)	0.0516 (5)
H5G	0.1019	−0.2829	0.7392	0.062*
H1	0.0541	0.1187	0.5885	0.069 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0316 (6)	0.0357 (6)	0.0472 (6)	0.0042 (4)	−0.0041 (5)	−0.0148 (5)
C1	0.0226 (7)	0.0226 (7)	0.0309 (7)	0.0004 (6)	0.0002 (6)	0.0045 (6)
C2	0.0268 (8)	0.0244 (8)	0.0332 (8)	0.0023 (6)	−0.0022 (6)	0.0008 (6)
C3	0.0291 (8)	0.0306 (8)	0.0362 (8)	0.0077 (6)	0.0045 (6)	0.0015 (6)
C4	0.0221 (7)	0.0335 (9)	0.0415 (8)	0.0021 (6)	0.0030 (6)	0.0079 (7)
N1G	0.0350 (7)	0.0332 (7)	0.0380 (7)	0.0005 (6)	0.0006 (5)	−0.0043 (6)
C5	0.0268 (8)	0.0392 (9)	0.0435 (9)	−0.0065 (7)	−0.0022 (7)	0.0063 (7)
C6	0.0389 (9)	0.0425 (10)	0.0432 (9)	−0.0129 (7)	−0.0054 (7)	−0.0039 (8)
C7	0.0408 (9)	0.0369 (9)	0.0379 (8)	−0.0049 (7)	0.0026 (7)	−0.0065 (7)
C8	0.0281 (8)	0.0328 (8)	0.0345 (8)	−0.0022 (6)	0.0018 (6)	−0.0008 (6)
C9	0.0250 (7)	0.0246 (8)	0.0294 (7)	−0.0018 (6)	0.0008 (6)	0.0056 (6)
C10	0.0251 (7)	0.0279 (8)	0.0327 (8)	−0.0024 (6)	−0.0015 (6)	0.0065 (6)
C2G	0.0328 (8)	0.0374 (9)	0.0350 (8)	−0.0055 (7)	−0.0025 (6)	−0.0053 (7)
C6G	0.0426 (9)	0.0482 (11)	0.0390 (9)	−0.0041 (8)	0.0058 (7)	−0.0044 (8)
C4G	0.0689 (13)	0.0314 (10)	0.0668 (12)	0.0056 (8)	−0.0169 (10)	0.0016 (9)
C3G	0.0519 (11)	0.0431 (11)	0.0524 (10)	0.0086 (8)	−0.0014 (8)	−0.0174 (9)
C1G	0.0655 (12)	0.0653 (13)	0.0413 (10)	−0.0105 (10)	0.0014 (8)	0.0050 (9)
C5G	0.0605 (12)	0.0476 (11)	0.0466 (10)	−0.0095 (9)	−0.0056 (8)	0.0105 (9)

Geometric parameters (Å, º)

O1—C2	1.3635 (16)	C8—C9	1.4159 (19)
O1—H1	0.9826	C8—H8	0.9500
C1—C2	1.3715 (19)	C9—C10	1.4280 (19)
C1—C9	1.4239 (19)	C2G—C3G	1.388 (2)
C1—C1^i	1.493 (2)	C2G—C1G	1.493 (2)
C2—C3	1.4187 (19)	C6G—C5G	1.364 (2)
C3—C4	1.3604 (19)	C6G—H6G	0.9500
C3—H3	0.9500	C4G—C5G	1.366 (2)
C4—C10	1.4137 (19)	C4G—C3G	1.371 (2)
C4—H4	0.9500	C4G—H4G	0.9500
N1G—C2G	1.3349 (18)	C3G—H3G	0.9500
N1G—C6G	1.3390 (19)	C1G—H1G1	0.9800
C5—C6	1.360 (2)	C1G—H1G3	0.9800
C5—C10	1.4144 (19)	C1G—H1G5	0.9800
C5—H5	0.9500	C1G—H1G4	0.9800
C6—C7	1.408 (2)	C1G—H1G6	0.9800
C6—H6	0.9500	C1G—H1G2	0.9800
C7—C8	1.3644 (19)	C5G—H5G	0.9500
C7—H7	0.9500
C2—O1—H1	111.9	C3G—C2G—C1G	121.84 (15)
C2—C1—C9	119.50 (12)	N1G—C6G—C5G	124.05 (16)
C2—C1—C1^i	119.73 (12)	N1G—C6G—H6G	118.0
C9—C1—C1^i	120.75 (12)	C5G—C6G—H6G	118.0
O1—C2—C1	118.81 (12)	C5G—C4G—C3G	119.29 (16)
O1—C2—C3	120.31 (12)	C5G—C4G—H4G	120.4
C1—C2—C3	120.86 (12)	C3G—C4G—H4G	120.4
C4—C3—C2	120.40 (13)	C4G—C3G—C2G	119.88 (16)
C4—C3—H3	119.8	C4G—C3G—H3G	120.1
C2—C3—H3	119.8	C2G—C3G—H3G	120.1
C3—C4—C10	120.90 (12)	C2G—C1G—H1G1	109.5
C3—C4—H4	119.5	C2G—C1G—H1G3	109.5
C10—C4—H4	119.5	H1G1—C1G—H1G3	109.5
C2G—N1G—C6G	118.04 (14)	C2G—C1G—H1G5	109.5
C6—C5—C10	121.26 (13)	H1G1—C1G—H1G5	109.5
C6—C5—H5	119.4	H1G3—C1G—H1G5	109.5
C10—C5—H5	119.4	C2G—C1G—H1G4	109.5
C5—C6—C7	120.10 (14)	H1G1—C1G—H1G4	141.1
C5—C6—H6	119.9	H1G3—C1G—H1G4	56.3
C7—C6—H6	119.9	H1G5—C1G—H1G4	56.3
C8—C7—C6	120.29 (14)	C2G—C1G—H1G6	109.5
C8—C7—H7	119.9	H1G1—C1G—H1G6	56.3
C6—C7—H7	119.9	H1G3—C1G—H1G6	141.1
C7—C8—C9	121.35 (13)	H1G5—C1G—H1G6	56.3
C7—C8—H8	119.3	H1G4—C1G—H1G6	109.5
C9—C8—H8	119.3	C2G—C1G—H1G2	109.5
C8—C9—C1	122.29 (12)	H1G1—C1G—H1G2	56.3
C8—C9—C10	118.13 (12)	H1G3—C1G—H1G2	56.3
C1—C9—C10	119.58 (12)	H1G5—C1G—H1G2	141.1
C4—C10—C5	122.38 (12)	H1G4—C1G—H1G2	109.5
C4—C10—C9	118.74 (12)	H1G6—C1G—H1G2	109.5
C5—C10—C9	118.87 (13)	C6G—C5G—C4G	117.93 (16)
N1G—C2G—C3G	120.81 (14)	C6G—C5G—H5G	121.0
N1G—C2G—C1G	117.35 (15)	C4G—C5G—H5G	121.0
C9—C1—C2—O1	−178.76 (12)	C3—C4—C10—C5	−179.26 (13)
C1^i—C1—C2—O1	2.70 (18)	C3—C4—C10—C9	1.22 (19)
C9—C1—C2—C3	0.1 (2)	C6—C5—C10—C4	−179.32 (14)
C1^i—C1—C2—C3	−178.49 (12)	C6—C5—C10—C9	0.2 (2)
O1—C2—C3—C4	179.28 (12)	C8—C9—C10—C4	179.05 (12)
C1—C2—C3—C4	0.5 (2)	C1—C9—C10—C4	−0.67 (19)
C2—C3—C4—C10	−1.1 (2)	C8—C9—C10—C5	−0.50 (19)
C10—C5—C6—C7	0.1 (2)	C1—C9—C10—C5	179.79 (12)
C5—C6—C7—C8	−0.2 (2)	C6G—N1G—C2G—C3G	0.2 (2)
C6—C7—C8—C9	−0.1 (2)	C6G—N1G—C2G—C1G	−179.75 (13)
C7—C8—C9—C1	−179.82 (13)	C2G—N1G—C6G—C5G	−0.1 (2)
C7—C8—C9—C10	0.5 (2)	C5G—C4G—C3G—C2G	−0.4 (3)
C2—C1—C9—C8	−179.65 (12)	N1G—C2G—C3G—C4G	0.1 (2)
C1^i—C1—C9—C8	−1.12 (19)	C1G—C2G—C3G—C4G	179.98 (14)
C2—C1—C9—C10	0.05 (19)	N1G—C6G—C5G—C4G	−0.3 (2)
C1^i—C1—C9—C10	178.58 (11)	C3G—C4G—C5G—C6G	0.5 (2)

Symmetry code: (i) −x, y, −z+3/2.

(BNP3P)

Crystal data

C32H28N2O2	Z = 4
Mr = 472.56	F(000) = 1000
Monoclinic, P21/c	Dx = 1.211 Mg m^−3
a = 12.118 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.2614 (10) Å	µ = 0.08 mm^−1
c = 16.581 (1) Å	T = 173 K
β = 103.448 (2)°	0.37 × 0.1 × 0.1 mm
V = 2591.5 (3) Å^3

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 26.4°, θmin = 2.7°
13104 measured reflections	h = −14→15
4826 independent reflections	k = −16→16
3380 reflections with I > 2σ(I)	l = −16→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full with fixed elements per cycle	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0463P)^2 + 0.4284P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.023
4826 reflections	Δρmax = 0.18 e Å^−3
335 parameters	Δρmin = −0.15 e Å^−3
4 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0100 (9)

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	0.86896 (9)	0.41473 (8)	0.15494 (6)	0.045
O2	0.60016 (8)	0.33082 (8)	0.19884 (7)	0.048
C1	0.83816 (10)	0.34891 (10)	0.28372 (8)	0.029
C10	0.95225 (11)	0.20023 (10)	0.34237 (8)	0.033
C8	0.81898 (12)	0.27100 (11)	0.41643 (8)	0.034
H8	0.7631	0.3195	0.4209	0.041*
C2	0.88951 (11)	0.34678 (11)	0.21802 (8)	0.032
C4	1.00000 (11)	0.20026 (11)	0.27209 (9)	0.037
H4	1.0542	0.1503	0.2671	0.044*
C9	0.86956 (10)	0.27463 (10)	0.34769 (8)	0.030
C20	0.69292 (13)	0.58047 (11)	0.35176 (9)	0.041
C5	0.98189 (12)	0.12750 (11)	0.40586 (9)	0.041
H5	1.0376	0.0781	0.4028	0.049*
C7	0.84913 (13)	0.19896 (11)	0.47643 (9)	0.041
H7	0.8136	0.1977	0.5218	0.049*
C11	0.74987 (11)	0.42533 (10)	0.28972 (8)	0.030
C18	0.89151 (12)	0.53160 (11)	0.38603 (9)	0.040
H18	0.9505	0.4870	0.3803	0.047*
C12	0.63804 (11)	0.41038 (11)	0.24927 (9)	0.035
C3	0.96911 (11)	0.27098 (11)	0.21183 (9)	0.037
H3	1.0015	0.2695	0.1649	0.044*
N1GA	0.70289 (10)	0.14878 (10)	0.17688 (8)	0.047
C19	0.77874 (11)	0.51187 (10)	0.34203 (8)	0.033
C14	0.57969 (13)	0.56138 (12)	0.30884 (10)	0.049
H14	0.5212	0.6064	0.3149	0.059*
C2GA	0.72579 (12)	0.08309 (12)	0.23950 (10)	0.045
H2GA	0.7116	0.1038	0.2910	0.055*
N1GB	0.28256 (11)	0.43465 (11)	−0.10564 (8)	0.053
C13	0.55363 (12)	0.47946 (12)	0.25911 (10)	0.047
H13	0.4771	0.4684	0.2304	0.056*
C6	0.93188 (13)	0.12687 (12)	0.47169 (9)	0.045
H6	0.9532	0.0777	0.5141	0.055*
C16	0.83157 (16)	0.68121 (13)	0.44583 (11)	0.058
H16	0.8500	0.7383	0.4810	0.070*
C15	0.72260 (15)	0.66480 (12)	0.40442 (11)	0.055
H15	0.6652	0.7108	0.4109	0.065*
C17	0.91675 (15)	0.61385 (12)	0.43658 (10)	0.052
H17	0.9929	0.6255	0.4658	0.062*
C6GA	0.72281 (15)	0.11843 (14)	0.10520 (11)	0.056
H6GA	0.7060	0.1634	0.0594	0.068*
C2GB	0.32975 (14)	0.35721 (14)	−0.13514 (11)	0.057
H2GB	0.3002	0.3389	−0.1914	0.068*
C3GA	0.76858 (13)	−0.01274 (13)	0.23502 (11)	0.050
C3GB	0.41923 (14)	0.30084 (13)	−0.08975 (11)	0.056
C6GB	0.32470 (15)	0.45865 (14)	−0.02649 (11)	0.060
H6GB	0.2923	0.5139	−0.0037	0.071*
C4GB	0.45985 (14)	0.32826 (14)	−0.00866 (11)	0.059
H4GB	0.5211	0.2921	0.0252	0.071*
C5GB	0.41257 (16)	0.40730 (16)	0.02349 (11)	0.067
H5GB	0.4401	0.4265	0.0798	0.080*
C5GA	0.76646 (17)	0.02529 (14)	0.09400 (12)	0.068
H5GA	0.7805	0.0068	0.0419	0.081*
C1GB	0.4693 (2)	0.21539 (18)	−0.12950 (16)	0.098
H1B1	0.4278	0.2084	−0.1875	0.147*	0.50
H1B2	0.4633	0.1526	−0.0997	0.147*	0.50
H1B3	0.5493	0.2296	−0.1272	0.147*	0.50
H1B5	0.5324	0.1853	−0.0888	0.147*	0.50
H1B6	0.4970	0.2412	−0.1766	0.147*	0.50
H1B4	0.4110	0.1641	−0.1490	0.147*	0.50
C4GA	0.78948 (16)	−0.04077 (14)	0.15979 (12)	0.064
H4GA	0.8197	−0.1056	0.1534	0.077*
C1GA	0.79134 (18)	−0.08099 (16)	0.30914 (13)	0.076
H1A2	0.8725	−0.0799	0.3357	0.114*
H1A1	0.7684	−0.1499	0.2915	0.114*
H1A3	0.7479	−0.0578	0.3486	0.114*
H2	0.6532 (13)	0.2774 (8)	0.1980 (10)	0.083*
H1	0.8139 (14)	0.4683 (11)	0.1549 (10)	0.097*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.058	0.046	0.035	0.014	0.020	0.011
O2	0.038	0.047	0.051	0.004	−0.003	−0.012
C1	0.028	0.030	0.027	0.000	0.005	−0.002
C10	0.032	0.032	0.033	0.002	0.006	−0.001
C8	0.038	0.034	0.033	0.005	0.011	0.000
C2	0.035	0.034	0.027	0.001	0.007	0.001
C4	0.034	0.037	0.041	0.007	0.011	−0.002
C9	0.030	0.030	0.029	−0.001	0.005	−0.001
C20	0.050	0.033	0.045	0.004	0.019	0.000
C5	0.043	0.035	0.044	0.009	0.009	0.004
C7	0.053	0.038	0.035	0.003	0.017	0.004
C11	0.034	0.031	0.027	0.004	0.010	0.003
C18	0.045	0.035	0.038	−0.004	0.009	0.003
C12	0.035	0.036	0.035	0.003	0.006	0.000
C3	0.038	0.041	0.035	0.003	0.016	−0.002
N1GA	0.041	0.041	0.061	−0.005	0.017	−0.006
C19	0.040	0.031	0.030	0.001	0.012	0.005
C14	0.043	0.043	0.065	0.013	0.019	−0.002
C2GA	0.037	0.048	0.053	−0.006	0.012	−0.009
N1GB	0.053	0.060	0.048	0.013	0.017	0.015
C13	0.033	0.049	0.057	0.008	0.008	0.000
C6	0.059	0.037	0.040	0.008	0.011	0.011
C16	0.088	0.035	0.054	−0.012	0.021	−0.010
C15	0.073	0.035	0.062	0.005	0.029	−0.007
C17	0.062	0.043	0.046	−0.016	0.005	−0.001
C6GA	0.065	0.051	0.059	−0.006	0.024	0.002
C2GB	0.053	0.067	0.051	0.007	0.013	0.004
C3GA	0.043	0.047	0.061	0.000	0.015	−0.001
C3GB	0.047	0.050	0.071	0.004	0.016	0.003
C6GB	0.069	0.064	0.049	0.019	0.020	0.009
C4GB	0.051	0.062	0.062	0.010	0.008	0.019
C5GB	0.073	0.079	0.045	0.017	0.008	0.008
C5GA	0.090	0.057	0.066	0.001	0.041	−0.009
C1GB	0.086	0.083	0.121	0.028	0.015	−0.026
C4GA	0.073	0.044	0.083	0.008	0.033	−0.009
C1GA	0.076	0.073	0.077	0.016	0.016	0.015

Geometric parameters (Å, º)

O1—C2	1.3590 (16)	C2GA—H2GA	0.9500
O1—H1	0.974 (8)	N1GB—C2GB	1.323 (2)
O2—C12	1.3581 (17)	N1GB—C6GB	1.331 (2)
O2—H2	0.959 (8)	C13—H13	0.9500
C1—C2	1.3748 (19)	C6—H6	0.9500
C1—C9	1.4326 (18)	C16—C15	1.357 (2)
C1—C11	1.4937 (18)	C16—C17	1.400 (2)
C10—C5	1.4113 (19)	C16—H16	0.9500
C10—C4	1.416 (2)	C15—H15	0.9500
C10—C9	1.4235 (19)	C17—H17	0.9500
C8—C7	1.3663 (19)	C6GA—C5GA	1.373 (2)
C8—C9	1.4149 (19)	C6GA—H6GA	0.9500
C8—H8	0.9500	C2GB—C3GB	1.386 (2)
C2—C3	1.4133 (19)	C2GB—H2GB	0.9500
C4—C3	1.3580 (19)	C3GA—C4GA	1.380 (2)
C4—H4	0.9500	C3GA—C1GA	1.499 (2)
C20—C15	1.413 (2)	C3GB—C4GB	1.369 (2)
C20—C14	1.414 (2)	C3GB—C1GB	1.508 (3)
C20—C19	1.419 (2)	C6GB—C5GB	1.369 (2)
C5—C6	1.366 (2)	C6GB—H6GB	0.9500
C5—H5	0.9500	C4GB—C5GB	1.361 (3)
C7—C6	1.401 (2)	C4GB—H4GB	0.9500
C7—H7	0.9500	C5GB—H5GB	0.9500
C11—C12	1.3794 (18)	C5GA—C4GA	1.376 (3)
C11—C19	1.4320 (19)	C5GA—H5GA	0.9500
C18—C17	1.366 (2)	C1GB—H1B1	0.9800
C18—C19	1.4158 (19)	C1GB—H1B2	0.9800
C18—H18	0.9500	C1GB—H1B3	0.9800
C12—C13	1.411 (2)	C1GB—H1B5	0.9800
C3—H3	0.9500	C1GB—H1B6	0.9800
N1GA—C6GA	1.329 (2)	C1GB—H1B4	0.9800
N1GA—C2GA	1.334 (2)	C4GA—H4GA	0.9500
C14—C13	1.356 (2)	C1GA—H1A2	0.9800
C14—H14	0.9500	C1GA—H1A1	0.9800
C2GA—C3GA	1.381 (2)	C1GA—H1A3	0.9800
C2—O1—H1	119.1 (10)	C16—C15—C20	121.17 (16)
C12—O2—H2	116.8 (10)	C16—C15—H15	119.4
C2—C1—C9	118.77 (12)	C20—C15—H15	119.4
C2—C1—C11	122.00 (12)	C18—C17—C16	120.73 (15)
C9—C1—C11	119.22 (11)	C18—C17—H17	119.6
C5—C10—C4	122.15 (13)	C16—C17—H17	119.6
C5—C10—C9	119.22 (12)	N1GA—C6GA—C5GA	123.31 (17)
C4—C10—C9	118.61 (12)	N1GA—C6GA—H6GA	118.3
C7—C8—C9	121.18 (13)	C5GA—C6GA—H6GA	118.3
C7—C8—H8	119.4	N1GB—C2GB—C3GB	124.65 (17)
C9—C8—H8	119.4	N1GB—C2GB—H2GB	117.7
O1—C2—C1	124.09 (12)	C3GB—C2GB—H2GB	117.7
O1—C2—C3	114.94 (12)	C4GA—C3GA—C2GA	116.52 (16)
C1—C2—C3	120.96 (13)	C4GA—C3GA—C1GA	122.73 (17)
C3—C4—C10	120.67 (13)	C2GA—C3GA—C1GA	120.74 (16)
C3—C4—H4	119.7	C4GB—C3GB—C2GB	116.56 (16)
C10—C4—H4	119.7	C4GB—C3GB—C1GB	122.66 (17)
C8—C9—C10	117.99 (12)	C2GB—C3GB—C1GB	120.77 (18)
C8—C9—C1	121.98 (12)	N1GB—C6GB—C5GB	122.95 (17)
C10—C9—C1	120.02 (12)	N1GB—C6GB—H6GB	118.5
C15—C20—C14	122.04 (14)	C5GB—C6GB—H6GB	118.5
C15—C20—C19	119.33 (14)	C5GB—C4GB—C3GB	120.07 (16)
C14—C20—C19	118.63 (14)	C5GB—C4GB—H4GB	120.0
C6—C5—C10	121.13 (14)	C3GB—C4GB—H4GB	120.0
C6—C5—H5	119.4	C4GB—C5GB—C6GB	119.01 (17)
C10—C5—H5	119.4	C4GB—C5GB—H5GB	120.5
C8—C7—C6	120.67 (14)	C6GB—C5GB—H5GB	120.5
C8—C7—H7	119.7	C6GA—C5GA—C4GA	118.61 (17)
C6—C7—H7	119.7	C6GA—C5GA—H5GA	120.7
C12—C11—C19	118.93 (12)	C4GA—C5GA—H5GA	120.7
C12—C11—C1	120.53 (12)	C3GB—C1GB—H1B1	109.5
C19—C11—C1	120.41 (11)	C3GB—C1GB—H1B2	109.5
C17—C18—C19	121.01 (15)	H1B1—C1GB—H1B2	109.5
C17—C18—H18	119.5	C3GB—C1GB—H1B3	109.5
C19—C18—H18	119.5	H1B1—C1GB—H1B3	109.5
O2—C12—C11	124.34 (12)	H1B2—C1GB—H1B3	109.5
O2—C12—C13	115.17 (12)	C3GB—C1GB—H1B5	109.5
C11—C12—C13	120.48 (13)	H1B1—C1GB—H1B5	141.1
C4—C3—C2	120.92 (13)	H1B2—C1GB—H1B5	56.3
C4—C3—H3	119.5	H1B3—C1GB—H1B5	56.3
C2—C3—H3	119.5	C3GB—C1GB—H1B6	109.5
C6GA—N1GA—C2GA	116.75 (14)	H1B1—C1GB—H1B6	56.3
C18—C19—C20	117.91 (13)	H1B2—C1GB—H1B6	141.1
C18—C19—C11	122.06 (13)	H1B3—C1GB—H1B6	56.3
C20—C19—C11	120.03 (13)	H1B5—C1GB—H1B6	109.5
C13—C14—C20	120.73 (14)	C3GB—C1GB—H1B4	109.5
C13—C14—H14	119.6	H1B1—C1GB—H1B4	56.3
C20—C14—H14	119.6	H1B2—C1GB—H1B4	56.3
N1GA—C2GA—C3GA	124.87 (15)	H1B3—C1GB—H1B4	141.1
N1GA—C2GA—H2GA	117.6	H1B5—C1GB—H1B4	109.5
C3GA—C2GA—H2GA	117.6	H1B6—C1GB—H1B4	109.5
C2GB—N1GB—C6GB	116.76 (14)	C5GA—C4GA—C3GA	119.93 (17)
C14—C13—C12	121.20 (14)	C5GA—C4GA—H4GA	120.0
C14—C13—H13	119.4	C3GA—C4GA—H4GA	120.0
C12—C13—H13	119.4	C3GA—C1GA—H1A2	109.5
C5—C6—C7	119.80 (14)	C3GA—C1GA—H1A1	109.5
C5—C6—H6	120.1	H1A2—C1GA—H1A1	109.5
C7—C6—H6	120.1	C3GA—C1GA—H1A3	109.5
C15—C16—C17	119.85 (15)	H1A2—C1GA—H1A3	109.5
C15—C16—H16	120.1	H1A1—C1GA—H1A3	109.5
C17—C16—H16	120.1
C9—C1—C2—O1	−178.17 (12)	C15—C20—C19—C11	179.20 (13)
C11—C1—C2—O1	2.6 (2)	C14—C20—C19—C11	−0.1 (2)
C9—C1—C2—C3	2.1 (2)	C12—C11—C19—C18	179.44 (13)
C11—C1—C2—C3	−177.13 (12)	C1—C11—C19—C18	3.6 (2)
C5—C10—C4—C3	179.59 (13)	C12—C11—C19—C20	0.1 (2)
C9—C10—C4—C3	1.2 (2)	C1—C11—C19—C20	−175.70 (12)
C7—C8—C9—C10	0.6 (2)	C15—C20—C14—C13	−179.58 (16)
C7—C8—C9—C1	179.31 (13)	C19—C20—C14—C13	−0.3 (2)
C5—C10—C9—C8	−1.11 (19)	C6GA—N1GA—C2GA—C3GA	0.3 (2)
C4—C10—C9—C8	177.29 (12)	C20—C14—C13—C12	0.6 (2)
C5—C10—C9—C1	−179.83 (12)	O2—C12—C13—C14	178.93 (14)
C4—C10—C9—C1	−1.43 (19)	C11—C12—C13—C14	−0.6 (2)
C2—C1—C9—C8	−178.89 (13)	C10—C5—C6—C7	0.4 (2)
C11—C1—C9—C8	0.34 (19)	C8—C7—C6—C5	−1.0 (2)
C2—C1—C9—C10	−0.21 (19)	C17—C16—C15—C20	0.0 (3)
C11—C1—C9—C10	179.02 (12)	C14—C20—C15—C16	179.23 (16)
C4—C10—C5—C6	−177.74 (14)	C19—C20—C15—C16	−0.1 (2)
C9—C10—C5—C6	0.6 (2)	C19—C18—C17—C16	−0.3 (2)
C9—C8—C7—C6	0.4 (2)	C15—C16—C17—C18	0.2 (3)
C2—C1—C11—C12	83.48 (17)	C2GA—N1GA—C6GA—C5GA	−1.0 (2)
C9—C1—C11—C12	−95.72 (16)	C6GB—N1GB—C2GB—C3GB	−0.4 (3)
C2—C1—C11—C19	−100.74 (16)	N1GA—C2GA—C3GA—C4GA	0.6 (2)
C9—C1—C11—C19	80.06 (16)	N1GA—C2GA—C3GA—C1GA	−179.93 (15)
C19—C11—C12—O2	−179.30 (13)	N1GB—C2GB—C3GB—C4GB	0.4 (3)
C1—C11—C12—O2	−3.5 (2)	N1GB—C2GB—C3GB—C1GB	−178.45 (19)
C19—C11—C12—C13	0.2 (2)	C2GB—N1GB—C6GB—C5GB	0.1 (3)
C1—C11—C12—C13	176.05 (13)	C2GB—C3GB—C4GB—C5GB	0.0 (3)
C10—C4—C3—C2	0.6 (2)	C1GB—C3GB—C4GB—C5GB	178.79 (19)
O1—C2—C3—C4	177.90 (12)	C3GB—C4GB—C5GB—C6GB	−0.3 (3)
C1—C2—C3—C4	−2.3 (2)	N1GB—C6GB—C5GB—C4GB	0.2 (3)
C17—C18—C19—C20	0.3 (2)	N1GA—C6GA—C5GA—C4GA	0.9 (3)
C17—C18—C19—C11	−178.98 (14)	C6GA—C5GA—C4GA—C3GA	0.0 (3)
C15—C20—C19—C18	−0.1 (2)	C2GA—C3GA—C4GA—C5GA	−0.7 (3)
C14—C20—C19—C18	−179.44 (13)	C1GA—C3GA—C4GA—C5GA	179.82 (18)

(BNP4P)

Crystal data

C32H28N2O2	Z = 8
Mr = 472.56	F(000) = 2000
Orthorhombic, Pbca	Dx = 1.249 Mg m^−3
Hall symbol: -P 2ac 2ab	Mo Kα radiation, λ = 0.71073 Å
a = 18.119 (3) Å	µ = 0.08 mm^−1
b = 10.812 (2) Å	T = 173 K
c = 25.665 (5) Å	0.50 × 0.30 × 0.10 mm
V = 5027.8 (2) Å^3

Data collection

Radiation source: fine-focus sealed tube	Rint = 0.053
Graphite monochromator	θmax = 25.4°, θmin = 2.3°
17012 measured reflections	h = −20→19
4135 independent reflections	k = −9→11
2669 reflections with I > 2σ(I)	l = −26→28

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)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.112	w = 1/[σ^2(Fo^2) + (0.0544P)^2 + 0.5718P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
4135 reflections	Δρmax = 0.17 e Å^−3
335 parameters	Δρmin = −0.17 e Å^−3
4 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0027 (4)

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	0.17997 (8)	0.96432 (11)	0.44201 (5)	0.0468 (4)
O2	0.17728 (8)	0.74722 (11)	0.31590 (5)	0.0457 (4)
C9	0.08568 (10)	1.00491 (16)	0.31712 (7)	0.0332 (5)
N1GA	0.22553 (9)	0.59174 (15)	0.50627 (6)	0.0462 (4)
C1	0.11105 (10)	0.94970 (15)	0.36441 (7)	0.0325 (5)
N1GB	0.19436 (10)	0.55377 (14)	0.24770 (6)	0.0465 (5)
C2	0.15440 (11)	1.01858 (16)	0.39768 (7)	0.0366 (5)
C12	0.12729 (11)	0.72183 (16)	0.35377 (7)	0.0366 (5)
C3	0.17226 (11)	1.14272 (17)	0.38606 (8)	0.0417 (5)
H3	0.2022	1.1889	0.4094	0.050*
C8	0.04495 (11)	0.93800 (17)	0.27934 (7)	0.0412 (5)
H8	0.0320	0.8544	0.2861	0.049*
C19	0.03621 (10)	0.79301 (16)	0.41574 (7)	0.0342 (5)
C6	0.04176 (12)	1.1150 (2)	0.22262 (8)	0.0515 (6)
H6	0.0273	1.1512	0.1905	0.062*
C11	0.09152 (11)	0.81889 (15)	0.37784 (7)	0.0337 (5)
C10	0.10368 (10)	1.13028 (16)	0.30576 (7)	0.0363 (5)
C4GB	0.19393 (11)	0.36221 (17)	0.17365 (7)	0.0418 (5)
C20	0.01984 (11)	0.66810 (17)	0.42944 (7)	0.0388 (5)
C13	0.11232 (12)	0.59832 (17)	0.36863 (8)	0.0438 (5)
H13	0.1387	0.5325	0.3527	0.053*
C14	0.06068 (12)	0.57293 (18)	0.40537 (8)	0.0460 (5)
H14	0.0519	0.4894	0.4151	0.055*
C4	0.14683 (11)	1.19641 (17)	0.34169 (8)	0.0424 (5)
H4	0.1585	1.2805	0.3348	0.051*
C4GA	0.11866 (11)	0.68427 (17)	0.57577 (8)	0.0425 (5)
C6GA	0.18986 (12)	0.69864 (18)	0.49783 (8)	0.0486 (6)
H6GA	0.2013	0.7436	0.4671	0.058*
C5	0.07973 (11)	1.18244 (18)	0.25811 (8)	0.0460 (5)
H5	0.0905	1.2667	0.2508	0.055*
C18	−0.00492 (11)	0.88718 (17)	0.44075 (7)	0.0408 (5)
H18	0.0049	0.9711	0.4323	0.049*
C17	−0.05822 (12)	0.86091 (19)	0.47656 (8)	0.0489 (6)
H17	−0.0848	0.9263	0.4926	0.059*
C15	−0.03574 (12)	0.64416 (19)	0.46679 (8)	0.0481 (6)
H15	−0.0465	0.5610	0.4760	0.058*
C5GA	0.13793 (12)	0.74679 (17)	0.53090 (8)	0.0448 (5)
H5GA	0.1151	0.8236	0.5229	0.054*
C3GA	0.15549 (13)	0.57397 (18)	0.58480 (8)	0.0507 (6)
H3GA	0.1449	0.5272	0.6152	0.061*
C2GB	0.14395 (12)	0.54666 (18)	0.21017 (8)	0.0498 (6)
H2GB	0.1070	0.6089	0.2090	0.060*
C2GA	0.20717 (13)	0.53215 (18)	0.54999 (8)	0.0504 (6)
H2GA	0.2314	0.4562	0.5574	0.061*
C7	0.02392 (12)	0.99114 (19)	0.23352 (8)	0.0477 (6)
H7	−0.0030	0.9440	0.2087	0.057*
C3GB	0.14184 (12)	0.45531 (19)	0.17302 (8)	0.0492 (6)
H3GB	0.1046	0.4562	0.1470	0.059*
C16	−0.07414 (12)	0.7375 (2)	0.48984 (8)	0.0536 (6)
H16	−0.1114	0.7195	0.5147	0.064*
C1GB	0.19164 (13)	0.25622 (19)	0.13582 (9)	0.0619 (7)
H1B1	0.2332	0.2004	0.1426	0.093*	0.50
H1B2	0.1951	0.2881	0.1002	0.093*	0.50
H1B3	0.1452	0.2110	0.1400	0.093*	0.50
H1B4	0.1491	0.2659	0.1126	0.093*	0.50
H1B5	0.1872	0.1782	0.1550	0.093*	0.50
H1B6	0.2371	0.2554	0.1152	0.093*	0.50
C5GB	0.24671 (12)	0.36969 (18)	0.21225 (8)	0.0503 (6)
H5GB	0.2845	0.3089	0.2142	0.060*
C6GB	0.24516 (13)	0.46476 (18)	0.24809 (8)	0.0504 (6)
H6GB	0.2821	0.4668	0.2743	0.061*
C1GA	0.06056 (14)	0.7335 (2)	0.61214 (9)	0.0638 (7)
H1A2	0.0666	0.8231	0.6159	0.096*
H1A1	0.0657	0.6938	0.6463	0.096*
H1A3	0.0115	0.7156	0.5979	0.096*
H1	0.2130 (11)	1.0163 (18)	0.4623 (8)	0.093 (9)*
H2	0.1882 (13)	0.6750 (15)	0.2945 (7)	0.094 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0604 (11)	0.0373 (8)	0.0427 (9)	−0.0085 (7)	−0.0140 (7)	0.0062 (6)
O2	0.0503 (10)	0.0376 (8)	0.0490 (9)	0.0040 (7)	0.0076 (7)	−0.0033 (6)
C9	0.0309 (11)	0.0310 (11)	0.0376 (11)	0.0042 (8)	0.0038 (9)	0.0013 (8)
N1GA	0.0515 (12)	0.0414 (10)	0.0458 (11)	0.0049 (9)	−0.0021 (9)	0.0015 (8)
C1	0.0350 (12)	0.0275 (10)	0.0351 (11)	0.0022 (8)	0.0028 (9)	0.0019 (8)
N1GB	0.0523 (12)	0.0407 (10)	0.0465 (11)	0.0026 (9)	−0.0012 (9)	−0.0040 (8)
C2	0.0431 (13)	0.0311 (11)	0.0355 (11)	0.0006 (9)	0.0011 (10)	0.0024 (9)
C12	0.0421 (13)	0.0336 (12)	0.0342 (11)	−0.0003 (9)	−0.0028 (10)	0.0011 (9)
C3	0.0441 (14)	0.0329 (12)	0.0483 (13)	−0.0075 (9)	−0.0019 (10)	−0.0011 (9)
C8	0.0433 (13)	0.0379 (12)	0.0425 (12)	0.0013 (9)	−0.0005 (10)	0.0025 (9)
C19	0.0393 (12)	0.0324 (11)	0.0310 (11)	−0.0036 (9)	−0.0060 (9)	0.0008 (8)
C6	0.0537 (15)	0.0586 (15)	0.0422 (13)	0.0066 (12)	−0.0038 (11)	0.0137 (10)
C11	0.0372 (13)	0.0294 (11)	0.0344 (11)	−0.0005 (9)	−0.0052 (10)	0.0002 (8)
C10	0.0353 (12)	0.0340 (12)	0.0397 (12)	0.0027 (9)	0.0052 (10)	0.0050 (9)
C4GB	0.0432 (14)	0.0408 (12)	0.0414 (12)	−0.0075 (10)	0.0038 (11)	−0.0007 (9)
C20	0.0440 (14)	0.0375 (12)	0.0350 (11)	−0.0070 (9)	−0.0079 (10)	0.0030 (9)
C13	0.0567 (15)	0.0304 (12)	0.0442 (13)	0.0032 (10)	−0.0067 (11)	−0.0033 (9)
C14	0.0621 (15)	0.0311 (12)	0.0449 (13)	−0.0077 (10)	−0.0099 (12)	0.0047 (9)
C4	0.0457 (14)	0.0303 (11)	0.0512 (13)	−0.0017 (9)	0.0051 (11)	0.0068 (9)
C4GA	0.0461 (14)	0.0388 (12)	0.0426 (13)	−0.0087 (10)	−0.0026 (10)	−0.0070 (9)
C6GA	0.0594 (16)	0.0467 (13)	0.0397 (12)	0.0092 (11)	0.0007 (11)	0.0068 (10)
C5	0.0444 (14)	0.0427 (12)	0.0509 (13)	0.0042 (10)	0.0032 (11)	0.0134 (10)
C18	0.0428 (13)	0.0392 (12)	0.0404 (12)	−0.0028 (10)	−0.0018 (11)	−0.0011 (9)
C17	0.0467 (15)	0.0547 (14)	0.0453 (13)	−0.0033 (11)	0.0038 (11)	−0.0051 (10)
C15	0.0557 (15)	0.0473 (13)	0.0415 (13)	−0.0157 (11)	−0.0080 (11)	0.0084 (10)
C5GA	0.0524 (14)	0.0416 (12)	0.0404 (12)	0.0070 (10)	−0.0039 (11)	0.0002 (9)
C3GA	0.0662 (17)	0.0412 (13)	0.0448 (13)	−0.0083 (11)	0.0039 (12)	0.0066 (10)
C2GB	0.0485 (15)	0.0460 (13)	0.0549 (15)	0.0116 (10)	−0.0030 (12)	0.0019 (10)
C2GA	0.0608 (16)	0.0367 (12)	0.0539 (14)	0.0030 (11)	−0.0032 (12)	0.0075 (10)
C7	0.0486 (15)	0.0518 (14)	0.0426 (13)	0.0038 (10)	−0.0080 (11)	0.0010 (10)
C3GB	0.0502 (15)	0.0535 (14)	0.0439 (13)	−0.0004 (11)	−0.0091 (11)	0.0004 (10)
C16	0.0517 (15)	0.0657 (16)	0.0434 (13)	−0.0145 (12)	0.0049 (12)	0.0040 (11)
C1GB	0.0726 (18)	0.0556 (14)	0.0575 (15)	−0.0117 (12)	0.0037 (13)	−0.0165 (11)
C5GB	0.0482 (14)	0.0414 (13)	0.0614 (15)	0.0079 (10)	−0.0055 (12)	−0.0071 (11)
C6GB	0.0456 (14)	0.0472 (13)	0.0585 (14)	0.0029 (11)	−0.0149 (11)	−0.0064 (11)
C1GA	0.0705 (18)	0.0611 (15)	0.0598 (15)	−0.0059 (13)	0.0119 (13)	−0.0110 (11)

Geometric parameters (Å, º)

O1—C2	1.361 (2)	C14—H14	0.9500
O1—H1	0.973 (7)	C4—H4	0.9500
O2—C12	1.357 (2)	C4GA—C5GA	1.380 (3)
O2—H2	0.975 (7)	C4GA—C3GA	1.386 (3)
C9—C8	1.417 (3)	C4GA—C1GA	1.504 (3)
C9—C10	1.424 (3)	C6GA—C5GA	1.370 (3)
C9—C1	1.429 (2)	C6GA—H6GA	0.9500
N1GA—C2GA	1.336 (2)	C5—H5	0.9500
N1GA—C6GA	1.342 (2)	C18—C17	1.363 (3)
C1—C2	1.379 (3)	C18—H18	0.9500
C1—C11	1.498 (2)	C17—C16	1.407 (3)
N1GB—C2GB	1.330 (3)	C17—H17	0.9500
N1GB—C6GB	1.332 (3)	C15—C16	1.361 (3)
C2—C3	1.412 (3)	C15—H15	0.9500
C12—C11	1.379 (2)	C5GA—H5GA	0.9500
C12—C13	1.415 (3)	C3GA—C2GA	1.371 (3)
C3—C4	1.359 (3)	C3GA—H3GA	0.9500
C3—H3	0.9500	C2GB—C3GB	1.373 (3)
C8—C7	1.363 (2)	C2GB—H2GB	0.9500
C8—H8	0.9500	C2GA—H2GA	0.9500
C19—C18	1.416 (3)	C7—H7	0.9500
C19—C11	1.424 (2)	C3GB—H3GB	0.9500
C19—C20	1.427 (2)	C16—H16	0.9500
C6—C5	1.354 (3)	C1GB—H1B1	0.9800
C6—C7	1.406 (3)	C1GB—H1B2	0.9800
C6—H6	0.9500	C1GB—H1B3	0.9800
C10—C4	1.404 (3)	C1GB—H1B4	0.9800
C10—C5	1.415 (3)	C1GB—H1B5	0.9800
C4GB—C5GB	1.379 (3)	C1GB—H1B6	0.9800
C4GB—C3GB	1.380 (3)	C5GB—C6GB	1.380 (3)
C4GB—C1GB	1.503 (3)	C5GB—H5GB	0.9500
C20—C14	1.410 (3)	C6GB—H6GB	0.9500
C20—C15	1.414 (3)	C1GA—H1A2	0.9800
C13—C14	1.356 (3)	C1GA—H1A1	0.9800
C13—H13	0.9500	C1GA—H1A3	0.9800
C2—O1—H1	114.1 (14)	C18—C17—C16	120.42 (19)
C12—O2—H2	112.1 (14)	C18—C17—H17	119.8
C8—C9—C10	117.72 (16)	C16—C17—H17	119.8
C8—C9—C1	122.38 (16)	C16—C15—C20	121.53 (18)
C10—C9—C1	119.86 (17)	C16—C15—H15	119.2
C2GA—N1GA—C6GA	115.55 (18)	C20—C15—H15	119.2
C2—C1—C9	118.93 (16)	C6GA—C5GA—C4GA	120.30 (19)
C2—C1—C11	120.14 (16)	C6GA—C5GA—H5GA	119.8
C9—C1—C11	120.93 (16)	C4GA—C5GA—H5GA	119.8
C2GB—N1GB—C6GB	116.00 (17)	C2GA—C3GA—C4GA	120.25 (19)
O1—C2—C1	118.60 (16)	C2GA—C3GA—H3GA	119.9
O1—C2—C3	120.53 (17)	C4GA—C3GA—H3GA	119.9
C1—C2—C3	120.88 (17)	N1GB—C2GB—C3GB	124.32 (19)
O2—C12—C11	118.72 (16)	N1GB—C2GB—H2GB	117.8
O2—C12—C13	120.80 (17)	C3GB—C2GB—H2GB	117.8
C11—C12—C13	120.49 (18)	N1GA—C2GA—C3GA	123.94 (19)
C4—C3—C2	120.34 (18)	N1GA—C2GA—H2GA	118.0
C4—C3—H3	119.8	C3GA—C2GA—H2GA	118.0
C2—C3—H3	119.8	C8—C7—C6	120.59 (19)
C7—C8—C9	121.38 (18)	C8—C7—H7	119.7
C7—C8—H8	119.3	C6—C7—H7	119.7
C9—C8—H8	119.3	C2GB—C3GB—C4GB	119.8 (2)
C18—C19—C11	122.60 (16)	C2GB—C3GB—H3GB	120.1
C18—C19—C20	117.36 (17)	C4GB—C3GB—H3GB	120.1
C11—C19—C20	120.04 (16)	C15—C16—C17	119.5 (2)
C5—C6—C7	119.73 (19)	C15—C16—H16	120.2
C5—C6—H6	120.1	C17—C16—H16	120.2
C7—C6—H6	120.1	C4GB—C1GB—H1B1	109.5
C12—C11—C19	119.13 (16)	C4GB—C1GB—H1B2	109.5
C12—C11—C1	120.29 (17)	H1B1—C1GB—H1B2	109.5
C19—C11—C1	120.58 (15)	C4GB—C1GB—H1B3	109.5
C4—C10—C5	122.36 (18)	H1B1—C1GB—H1B3	109.5
C4—C10—C9	118.53 (17)	H1B2—C1GB—H1B3	109.5
C5—C10—C9	119.07 (18)	C4GB—C1GB—H1B4	109.5
C5GB—C4GB—C3GB	116.10 (18)	H1B1—C1GB—H1B4	141.1
C5GB—C4GB—C1GB	121.87 (19)	H1B2—C1GB—H1B4	56.3
C3GB—C4GB—C1GB	121.99 (19)	H1B3—C1GB—H1B4	56.3
C14—C20—C15	122.49 (18)	C4GB—C1GB—H1B5	109.5
C14—C20—C19	118.28 (18)	H1B1—C1GB—H1B5	56.3
C15—C20—C19	119.23 (18)	H1B2—C1GB—H1B5	141.1
C14—C13—C12	120.70 (18)	H1B3—C1GB—H1B5	56.3
C14—C13—H13	119.7	H1B4—C1GB—H1B5	109.5
C12—C13—H13	119.7	C4GB—C1GB—H1B6	109.5
C13—C14—C20	121.26 (18)	H1B1—C1GB—H1B6	56.3
C13—C14—H14	119.4	H1B2—C1GB—H1B6	56.3
C20—C14—H14	119.4	H1B3—C1GB—H1B6	141.1
C3—C4—C10	121.44 (18)	H1B4—C1GB—H1B6	109.5
C3—C4—H4	119.3	H1B5—C1GB—H1B6	109.5
C10—C4—H4	119.3	C4GB—C5GB—C6GB	120.56 (19)
C5GA—C4GA—C3GA	116.04 (19)	C4GB—C5GB—H5GB	119.7
C5GA—C4GA—C1GA	121.44 (19)	C6GB—C5GB—H5GB	119.7
C3GA—C4GA—C1GA	122.51 (19)	N1GB—C6GB—C5GB	123.2 (2)
N1GA—C6GA—C5GA	123.92 (19)	N1GB—C6GB—H6GB	118.4
N1GA—C6GA—H6GA	118.0	C5GB—C6GB—H6GB	118.4
C5GA—C6GA—H6GA	118.0	C4GA—C1GA—H1A2	109.5
C6—C5—C10	121.50 (18)	C4GA—C1GA—H1A1	109.5
C6—C5—H5	119.3	H1A2—C1GA—H1A1	109.5
C10—C5—H5	119.3	C4GA—C1GA—H1A3	109.5
C17—C18—C19	121.92 (18)	H1A2—C1GA—H1A3	109.5
C17—C18—H18	119.0	H1A1—C1GA—H1A3	109.5
C19—C18—H18	119.0
C8—C9—C1—C2	175.86 (18)	C12—C13—C14—C20	0.7 (3)
C10—C9—C1—C2	−1.7 (3)	C15—C20—C14—C13	178.21 (19)
C8—C9—C1—C11	−3.8 (3)	C19—C20—C14—C13	−2.5 (3)
C10—C9—C1—C11	178.66 (17)	C2—C3—C4—C10	−1.3 (3)
C9—C1—C2—O1	−178.31 (16)	C5—C10—C4—C3	−176.76 (18)
C11—C1—C2—O1	1.4 (3)	C9—C10—C4—C3	1.1 (3)
C9—C1—C2—C3	1.5 (3)	C2GA—N1GA—C6GA—C5GA	0.2 (3)
C11—C1—C2—C3	−178.88 (17)	C7—C6—C5—C10	1.6 (3)
O1—C2—C3—C4	179.79 (18)	C4—C10—C5—C6	176.15 (19)
C1—C2—C3—C4	0.0 (3)	C9—C10—C5—C6	−1.7 (3)
C10—C9—C8—C7	0.3 (3)	C11—C19—C18—C17	179.31 (18)
C1—C9—C8—C7	−177.24 (18)	C20—C19—C18—C17	0.0 (3)
O2—C12—C11—C19	176.80 (16)	C19—C18—C17—C16	−0.1 (3)
C13—C12—C11—C19	−3.6 (3)	C14—C20—C15—C16	179.52 (19)
O2—C12—C11—C1	−3.6 (3)	C19—C20—C15—C16	0.2 (3)
C13—C12—C11—C1	176.05 (17)	N1GA—C6GA—C5GA—C4GA	−0.8 (3)
C18—C19—C11—C12	−177.58 (17)	C3GA—C4GA—C5GA—C6GA	0.9 (3)
C20—C19—C11—C12	1.7 (3)	C1GA—C4GA—C5GA—C6GA	−178.55 (19)
C18—C19—C11—C1	2.8 (3)	C5GA—C4GA—C3GA—C2GA	−0.6 (3)
C20—C19—C11—C1	−177.91 (16)	C1GA—C4GA—C3GA—C2GA	178.9 (2)
C2—C1—C11—C12	−103.0 (2)	C6GB—N1GB—C2GB—C3GB	−0.1 (3)
C9—C1—C11—C12	76.7 (2)	C6GA—N1GA—C2GA—C3GA	0.2 (3)
C2—C1—C11—C19	76.7 (2)	C4GA—C3GA—C2GA—N1GA	0.0 (3)
C9—C1—C11—C19	−103.7 (2)	C9—C8—C7—C6	−0.5 (3)
C8—C9—C10—C4	−177.20 (17)	C5—C6—C7—C8	−0.5 (3)
C1—C9—C10—C4	0.4 (3)	N1GB—C2GB—C3GB—C4GB	0.8 (3)
C8—C9—C10—C5	0.7 (3)	C5GB—C4GB—C3GB—C2GB	−1.2 (3)
C1—C9—C10—C5	178.35 (17)	C1GB—C4GB—C3GB—C2GB	176.49 (19)
C18—C19—C20—C14	−179.38 (17)	C20—C15—C16—C17	−0.3 (3)
C11—C19—C20—C14	1.3 (3)	C18—C17—C16—C15	0.2 (3)
C18—C19—C20—C15	−0.1 (3)	C3GB—C4GB—C5GB—C6GB	1.1 (3)
C11—C19—C20—C15	−179.40 (17)	C1GB—C4GB—C5GB—C6GB	−176.64 (19)
O2—C12—C13—C14	−177.95 (18)	C2GB—N1GB—C6GB—C5GB	−0.1 (3)
C11—C12—C13—C14	2.4 (3)	C4GB—C5GB—C6GB—N1GB	−0.5 (3)