Conformational dimorphism of the spiropyran 1',3',3'-trimethyl­spiro[2H-1-benzopyran-2,2'-indoline]-6-carbaldehyde)

The title compound, C₂₀H₁₉NO₂, crystallizes from an acetone-heptane solution as two dimorphs in the space groups C2/c and Cc. Each dimorph has two mol­ecules in the asymmetric unit. The four mol­ecules adopt slightly different conformations expressed by the degree of bending around a vector connecting the O and C atoms attached to the bridgehead C atom of the pyran ring. Due to the fact that all four mol­ecules are chemically identical, the difference in bending is attributed to packing forces. This is evident from the close contacts of neighbouring mol­ecules perpendicular to the plane of the benzopyran moiety observed in the Cc structure and not in the C2/c structure. These observations provide a unique example that shows how packing forces can affect the conformation of a specific mol­ecule.

S1. Comment

The design and synthesis of spiropyran derivatives are of great interest in photochemistry (Iyengar & Biewer, 2002; Godzi et al., 2001). For example, we have been interested in testing the photochemical behaviour of a single crystal composed of spiropyran as a guest molecule in inclusion compounds with light-stable host molecules. In the course of our studies, we found that the title compound, (I), crystallizes in two forms corresponding to different molecular conformations and crystal structures. Hence, they may be called conformational polymorphs, a subset of polymorphism in which molecules are folded into different three-dimensional conformations, which can then be packed into alternative crystal structures (Bernstein & Hagler, 1978).

Compound (I) crystallizes as colourless transparent plates in monoclinic space group C2/c, with two molecules, A and B, in the asymmetric unit (Fig. 1), and also as colourless transparent prisms in monoclinic space group Cc, with two molecules, A and B, in the asymmetric unit (Fig. 2). According to the density rule, the more tightly packed crystal with higher density is the more stable (Kitaigorodsky, 1973; Burger & Ramberger, 1979). The density of the spiropyran in the Cc form (1.243 Mg m^-3) is slightly higher than that in the C2/c form (1.228 Mg m^-3), indicating that it is probably more stable in the acentric space group. However, no experimental effort has been devoted to confirming this assumption.

The four molecules adopt significantly different conformations, expressed by the bending of the benzopyran part of the molecule; Fig. 3 shows the overlap of the four molecules of spiropyran in the two space groups. The molecules were positioned in the overlap diagram in such a way that their indoline parts including tetrahedral sp³ C atoms overlap completely, but the bending of the pyran ring with the aldehyde tail differs significantly in the four cases. The differences between the conformations of the four molecules may be attributed to the different degree of puckering of the pyran ring. Comparison of the angles α between the mean planes through atoms O2/C10/C9 and N1/C10/C11 shows that at the spiro atom, C10, the angles are close to the ideal of 90° (Table 1). At the hetero five-membered ring there is a bending around a vector connecting atoms N1···C11. This bending is expressed by the angles β between the mean planes through atoms N1/C10/C11 and N1/C19–C14/C11. The range of the angles β is too small to explain the differences in the conformation of the four molecules. The angle γ defines the angle between the mean planes through atoms O2/C10/C9 and O2/C5–C7/C2–C4/C8/C9. The γ angles are significantly different in the four molecules and determine the conformational variation. The bending angles in the two molecules that crystallize in space group Cc are different (17.2 and 20.0° in molecules A and B, respectively) and also different from those in the molecules which crystallize in space group C2/c (6.8 and -10.5° in molecules A and B, respectively), which have significantly smaller bending albeit to opposite sides. The bending of the benzopyran in space group C2/c is either towards the N1—C20 bond (molecule B) or towards the C11—C12 bond (molecule A), while in space group Cc the bending is towards the C11—C12 bond in both molecules.

A search of the Cambridge Structural Database (Version?; Allen, 2002) revealed 85 molecules containing a similar benzopyran moiety. In all of them, two methyl groups are bonded to the spiro C atom (C10). It was found that the range of the γ angles is from 0.0° (ZEMHUU; Matsumoto et al., 1995) to 42.2° (WUXGIF; Marek et al., 2003). No correlations were found between the bending angle γ and the bond distances involved with atom O2. Therefore, it is reasonable to assume that the bending does not result from electronic effects.

The differences between the conformations expressed by the degree of bending of the present molecules may be attributed to differences in packing rather than to differences in molecular properties. Close examination of the packing of the different dimorphs was carried out by calculating the intermolecular distances that are shorter than the sum of the Van der Waals radii of the atoms involved. It was shown that in space group Cc, there are several close contacts between the atoms of a neighbouring molecule and atoms belonging to the benzopyran moiety in an almost perpendicular orientation, thus determining the degree of bending (Table 2; Figs. 4b and 4c). In space group C2/c, there is only one such contact (Table 2; Figure 4a). The benzopyran ring is therefore blocked between neighbouring molecules in space group Cc and there is no such blocking in space group C2/c. Furthermore, the carbonyl atom O1 in the dimorph that crystallizes in C2/c is oriented in opposite directions in molecules A and B, while in space group Cc the carbonyl bonds are parallel (torsion angle C3—C2—C1—O1, Table 1). This difference in the orientation of the carbonyl O atom may also help to explain the existence of the dimorphic structures.

S2. Experimental

1',3'-Dihydro-1',3',3'-trimethyl-spiropyran-6-carbaldehyde was synthesized by the condensation reaction of 1,3,3-trimethyl-2-methylene-indoline and salicylaldehyde in boiling ethanol (Durr & Bouas-Laurent, 1990). After chromatographic purification, the product was recrystallized from an acetone–heptane solution (50:50 v/v) to give colourless crystals of (I) suitable for X-ray analysis.

S3. Refinement

H atoms were placed at calculated positions [C_aromatic—H = 0.93 Å and U_iso(H) = 1.2U_eq(C); C_methyl—H = 0.96 Å and U_iso(H) = 1.5U_eq(C)] and included as riding atoms. The absolute structure in space group Cc could not be assigned based on Friedel pairs, and the intensity data were merged.

Computing details

For both compounds, data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) and maXus (Mackay et al., 1998) for I_C2c; SHELXS97 (Sheldrick, 2008) for I_Cc. For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: Please give details.

Figures

	Fig. 1. The two independent molecules of (I) in the C2/c dimorph; only the atoms of molecule A are labelled. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The two independent molecules of (I) in the Cc dimorph; only the atoms of molecule A are labelled. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. Overlap of two the polymorphs. The two upper aldehyde parts belong to the dimorph in Cc and the two lower parts to that in C2/c.
	Fig. 4. Short intermolecular contacts (dashed lines) directed towards the benzopyran plane. (a) Space group C2/c [symmetry code: (i) 1/2-x, -1/2+y, 1/2-z]. (b) and (c) Space group Cc [symmetry codes: (i) -1/2+x, 1/2+y, z; (ii) 1/2+x, 1/2+y, z; (iii) 1+x, -y, 1/2+z; (iv) 1/2+x, -1/2+y, z].

(I_C2c) 1',3',3'-trimethylspiro[2'H-1-benzopyran-2,2'-indoline]-6-carbaldehyde

Crystal data

C20H19NO2	F(000) = 2592
Mr = 305.36	Dx = 1.228 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5256 reflections
a = 21.447 (4) Å	θ = 1.5–27.1°
b = 11.226 (2) Å	µ = 0.08 mm^−1
c = 28.221 (6) Å	T = 293 K
β = 103.57 (2)°	Plate, colourless
V = 6605 (2) Å^3	0.05 × 0.04 × 0.02 mm
Z = 16

Data collection

Nonius Kappa CCD diffractometer	3291 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.071
Graphite monochromator	θmax = 27.1°, θmin = 1.5°
Detector resolution: 95 pixels mm^-1	h = −27→24
ϕ and ω scans	k = −13→14
15238 measured reflections	l = −36→31
7218 independent 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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 0.89	w = 1/[σ^2(Fo^2) + (0.089P)^2] where P = (Fo^2 + 2Fc^2)/3
7218 reflections	(Δ/σ)max = 0.001
421 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Experimental. The X-ray diffraction data were collected at room temperature with Mo Kα radiation (λ = 0.71073 Å). The crystal structure was determined using the MAXUS direct method (Mackay et al., 1998), and refined anisotropically with respect to the non-H atoms using the SHELXL97 program package (Sheldrick, 2008).

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1A	0.07438 (11)	−0.21062 (18)	0.34421 (6)	0.1093 (7)
O2A	0.12216 (9)	0.05141 (12)	0.15604 (5)	0.0819 (6)
N1A	0.17770 (10)	0.20062 (17)	0.12514 (6)	0.0693 (5)
C1A	0.07174 (13)	−0.1095 (2)	0.33030 (8)	0.0798 (8)
H1A	0.0605	−0.0525	0.3508	0.096*
C2A	0.08424 (11)	−0.06607 (19)	0.28459 (7)	0.0574 (6)
C3A	0.08198 (10)	0.05404 (18)	0.27455 (7)	0.0549 (5)
H3A	0.0717	0.1069	0.2969	0.066*
C4A	0.09458 (11)	0.09804 (18)	0.23195 (7)	0.0541 (5)
C5A	0.10878 (11)	0.01680 (18)	0.19877 (7)	0.0555 (6)
C6A	0.11080 (12)	−0.10365 (19)	0.20812 (7)	0.0664 (7)
H6A	0.1201	−0.1568	0.1854	0.080*
C7A	0.09912 (12)	−0.14516 (19)	0.25103 (7)	0.0660 (6)
H7A	0.1012	−0.2264	0.2576	0.079*
C8A	0.09675 (13)	0.22299 (19)	0.22056 (7)	0.0749 (7)
H8A	0.0891	0.2792	0.2427	0.090*
C9A	0.10943 (14)	0.2592 (2)	0.17905 (8)	0.0849 (9)
H9A	0.1124	0.3407	0.1741	0.102*
C10A	0.11914 (13)	0.17743 (18)	0.14011 (7)	0.0632 (6)
C11A	0.06695 (11)	0.18554 (18)	0.09119 (7)	0.0580 (6)
C12A	0.00868 (14)	0.1081 (2)	0.09050 (10)	0.0953 (9)
H12A	−0.0094	0.1290	0.1174	0.143*
H12B	0.0213	0.0258	0.0931	0.143*
H12C	−0.0227	0.1204	0.0605	0.143*
C13A	0.04464 (12)	0.3164 (2)	0.08107 (8)	0.0767 (7)
H13A	0.0204	0.3403	0.1040	0.115*
H13B	0.0183	0.3227	0.0486	0.115*
H13C	0.0814	0.3671	0.0843	0.115*
C14A	0.10506 (10)	0.15073 (17)	0.05525 (7)	0.0521 (5)
C15A	0.08619 (12)	0.11874 (19)	0.00716 (7)	0.0667 (6)
H15A	0.0429	0.1092	−0.0074	0.080*
C16A	0.13198 (17)	0.1005 (2)	−0.01980 (9)	0.0832 (8)
H16A	0.1195	0.0795	−0.0525	0.100*
C17A	0.19535 (17)	0.1136 (2)	0.00218 (11)	0.0918 (9)
H17A	0.2256	0.1015	−0.0162	0.110*
C18A	0.21612 (13)	0.1441 (2)	0.05043 (10)	0.0824 (7)
H18A	0.2596	0.1516	0.0649	0.099*
C19A	0.16991 (11)	0.16328 (18)	0.07683 (8)	0.0575 (5)
C20A	0.23966 (15)	0.1915 (3)	0.15988 (10)	0.1254 (12)
H20A	0.2353	0.2162	0.1915	0.188*
H20B	0.2702	0.2418	0.1496	0.188*
H20C	0.2542	0.1104	0.1614	0.188*
O1B	0.08929 (10)	0.62079 (19)	−0.17353 (6)	0.1030 (7)
O2B	0.15464 (8)	0.56029 (12)	0.05707 (4)	0.0664 (4)
N1B	0.10932 (9)	0.68521 (15)	0.10739 (6)	0.0600 (5)
C1B	0.09587 (12)	0.5361 (3)	−0.14637 (8)	0.0775 (7)
H1B	0.0893	0.4607	−0.1603	0.093*
C2B	0.11347 (10)	0.5438 (2)	−0.09302 (7)	0.0558 (5)
C3B	0.12856 (10)	0.65224 (19)	−0.06980 (7)	0.0579 (6)
H3B	0.1289	0.7204	−0.0885	0.069*
C4B	0.14319 (10)	0.66158 (17)	−0.01951 (7)	0.0524 (5)
C5B	0.14118 (10)	0.55834 (18)	0.00758 (6)	0.0499 (5)
C6B	0.12738 (10)	0.44881 (18)	−0.01482 (7)	0.0544 (5)
H6B	0.1273	0.3804	0.0038	0.065*
C7B	0.11377 (10)	0.44203 (19)	−0.06482 (7)	0.0568 (6)
H7B	0.1046	0.3685	−0.0800	0.068*
C8B	0.16039 (12)	0.7719 (2)	0.00694 (8)	0.0727 (7)
H8B	0.1647	0.8411	−0.0102	0.087*
C9B	0.17005 (13)	0.7762 (2)	0.05470 (8)	0.0776 (7)
H9B	0.1818	0.8489	0.0701	0.093*
C10B	0.16332 (11)	0.67164 (18)	0.08566 (7)	0.0576 (6)
C11B	0.22043 (11)	0.6468 (2)	0.13037 (8)	0.0687 (6)
C12B	0.27025 (14)	0.5628 (3)	0.11802 (10)	0.1119 (11)
H12D	0.2861	0.5957	0.0917	0.168*
H12E	0.2509	0.4867	0.1085	0.168*
H12F	0.3051	0.5531	0.1461	0.168*
C13B	0.25282 (13)	0.7640 (3)	0.15145 (9)	0.0980 (9)
H13D	0.2743	0.7990	0.1286	0.147*
H13E	0.2835	0.7479	0.1815	0.147*
H13F	0.2209	0.8182	0.1574	0.147*
C14B	0.18550 (11)	0.59669 (19)	0.16640 (7)	0.0608 (6)
C19B	0.12102 (11)	0.62226 (17)	0.15099 (7)	0.0554 (6)
C18B	0.07783 (13)	0.5924 (2)	0.17899 (9)	0.0738 (7)
H18B	0.0343	0.6089	0.1681	0.089*
C17B	0.1012 (2)	0.5382 (2)	0.22296 (10)	0.0928 (10)
H17B	0.0730	0.5180	0.2422	0.111*
C15B	0.20761 (15)	0.5420 (2)	0.21114 (9)	0.0868 (8)
H15B	0.2510	0.5246	0.2223	0.104*
C16B	0.1646 (2)	0.5133 (2)	0.23920 (9)	0.0966 (10)
H16B	0.1793	0.4767	0.2693	0.116*
C20B	0.04514 (13)	0.6959 (3)	0.07677 (9)	0.0950 (9)
H20D	0.0464	0.7425	0.0485	0.142*
H20E	0.0179	0.7342	0.0947	0.142*
H20F	0.0286	0.6181	0.0668	0.142*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.161 (2)	0.0878 (14)	0.0885 (12)	0.0042 (13)	0.0485 (13)	0.0277 (11)
O2A	0.1491 (17)	0.0460 (9)	0.0600 (9)	0.0011 (9)	0.0438 (10)	−0.0012 (7)
N1A	0.0691 (14)	0.0745 (13)	0.0551 (11)	−0.0099 (11)	−0.0042 (10)	0.0050 (9)
C1A	0.103 (2)	0.0719 (18)	0.0692 (16)	0.0056 (15)	0.0291 (15)	0.0130 (13)
C2A	0.0633 (15)	0.0573 (14)	0.0508 (12)	0.0020 (11)	0.0116 (10)	0.0016 (10)
C3A	0.0578 (14)	0.0563 (14)	0.0476 (11)	0.0076 (10)	0.0067 (10)	−0.0062 (10)
C4A	0.0688 (15)	0.0463 (12)	0.0446 (11)	0.0035 (10)	0.0077 (10)	−0.0036 (9)
C5A	0.0744 (16)	0.0476 (13)	0.0438 (11)	0.0012 (11)	0.0123 (10)	−0.0003 (9)
C6A	0.098 (2)	0.0429 (13)	0.0622 (14)	0.0028 (12)	0.0278 (13)	−0.0045 (10)
C7A	0.0903 (19)	0.0474 (13)	0.0611 (14)	0.0031 (12)	0.0197 (13)	0.0045 (10)
C8A	0.124 (2)	0.0482 (14)	0.0528 (13)	0.0034 (14)	0.0217 (13)	−0.0072 (10)
C9A	0.147 (3)	0.0481 (14)	0.0609 (14)	0.0003 (15)	0.0275 (16)	−0.0027 (12)
C10A	0.0964 (19)	0.0436 (13)	0.0496 (12)	−0.0062 (12)	0.0175 (12)	−0.0010 (10)
C11A	0.0647 (15)	0.0533 (13)	0.0581 (13)	−0.0097 (11)	0.0187 (11)	−0.0046 (10)
C12A	0.084 (2)	0.097 (2)	0.115 (2)	−0.0311 (16)	0.0417 (17)	−0.0172 (17)
C13A	0.0735 (18)	0.0759 (17)	0.0822 (16)	0.0089 (14)	0.0211 (13)	−0.0017 (13)
C14A	0.0576 (14)	0.0481 (12)	0.0486 (12)	−0.0041 (10)	0.0086 (10)	−0.0010 (9)
C15A	0.0772 (17)	0.0618 (15)	0.0571 (14)	−0.0018 (12)	0.0076 (12)	−0.0037 (11)
C16A	0.124 (3)	0.0682 (17)	0.0619 (15)	0.0005 (17)	0.0322 (18)	−0.0045 (12)
C17A	0.115 (3)	0.0763 (19)	0.102 (2)	0.0053 (18)	0.062 (2)	0.0006 (16)
C18A	0.0606 (17)	0.0804 (18)	0.110 (2)	0.0079 (14)	0.0278 (16)	0.0116 (15)
C19A	0.0613 (15)	0.0538 (13)	0.0561 (13)	0.0001 (11)	0.0111 (11)	0.0057 (10)
C20A	0.097 (2)	0.156 (3)	0.094 (2)	−0.001 (2)	−0.0381 (17)	0.0049 (19)
O1B	0.1279 (18)	0.1248 (17)	0.0544 (10)	−0.0154 (13)	0.0172 (11)	0.0089 (10)
O2B	0.1003 (13)	0.0525 (9)	0.0437 (8)	−0.0083 (8)	0.0116 (8)	−0.0035 (6)
N1B	0.0552 (12)	0.0632 (12)	0.0601 (11)	0.0010 (9)	0.0100 (9)	0.0002 (9)
C1B	0.083 (2)	0.099 (2)	0.0532 (14)	−0.0136 (16)	0.0223 (13)	−0.0065 (14)
C2B	0.0501 (13)	0.0704 (15)	0.0483 (12)	−0.0069 (11)	0.0147 (10)	−0.0046 (11)
C3B	0.0587 (15)	0.0654 (14)	0.0528 (13)	−0.0018 (11)	0.0198 (10)	0.0074 (11)
C4B	0.0590 (14)	0.0486 (13)	0.0521 (12)	−0.0027 (10)	0.0182 (10)	0.0008 (10)
C5B	0.0517 (13)	0.0537 (13)	0.0446 (11)	−0.0032 (10)	0.0122 (9)	−0.0017 (9)
C6B	0.0604 (14)	0.0494 (13)	0.0540 (12)	−0.0054 (10)	0.0146 (10)	−0.0019 (10)
C7B	0.0536 (14)	0.0615 (14)	0.0568 (13)	−0.0065 (11)	0.0160 (10)	−0.0105 (10)
C8B	0.100 (2)	0.0552 (15)	0.0677 (15)	−0.0147 (13)	0.0293 (14)	0.0010 (11)
C9B	0.112 (2)	0.0558 (15)	0.0688 (15)	−0.0215 (14)	0.0291 (14)	−0.0136 (12)
C10B	0.0690 (15)	0.0534 (13)	0.0508 (12)	−0.0114 (11)	0.0149 (11)	−0.0113 (10)
C11B	0.0549 (15)	0.0866 (17)	0.0628 (14)	−0.0067 (13)	0.0106 (12)	−0.0195 (12)
C12B	0.072 (2)	0.151 (3)	0.113 (2)	0.0233 (19)	0.0200 (17)	−0.029 (2)
C13B	0.078 (2)	0.125 (2)	0.0886 (17)	−0.0451 (18)	0.0151 (15)	−0.0313 (16)
C14B	0.0674 (17)	0.0622 (14)	0.0470 (13)	−0.0034 (12)	0.0015 (11)	−0.0115 (10)
C19B	0.0662 (16)	0.0479 (13)	0.0533 (13)	−0.0036 (11)	0.0166 (12)	−0.0110 (10)
C18B	0.090 (2)	0.0574 (14)	0.0833 (17)	−0.0080 (13)	0.0389 (16)	−0.0126 (13)
C17B	0.159 (3)	0.0602 (17)	0.0711 (19)	−0.027 (2)	0.050 (2)	−0.0178 (14)
C15B	0.099 (2)	0.0826 (19)	0.0623 (16)	−0.0028 (16)	−0.0143 (15)	−0.0124 (13)
C16B	0.166 (3)	0.0678 (18)	0.0476 (15)	−0.020 (2)	0.009 (2)	−0.0066 (12)
C20B	0.0681 (19)	0.108 (2)	0.0990 (19)	0.0171 (16)	−0.0003 (15)	0.0107 (16)

Geometric parameters (Å, º)

O1A—C1A	1.198 (3)	O1B—C1B	1.209 (3)
O2A—C5A	1.360 (2)	O2B—C5B	1.359 (2)
O2A—C10A	1.481 (2)	O2B—C10B	1.476 (2)
N1A—C19A	1.398 (3)	N1B—C19B	1.390 (3)
N1A—C10A	1.440 (3)	N1B—C10B	1.440 (3)
N1A—C20A	1.458 (3)	N1B—C20B	1.448 (3)
C1A—C2A	1.461 (3)	C1B—C2B	1.466 (3)
C1A—H1A	0.9300	C1B—H1B	0.9300
C2A—C3A	1.376 (3)	C2B—C3B	1.385 (3)
C2A—C7A	1.389 (3)	C2B—C7B	1.391 (3)
C3A—C4A	1.384 (3)	C3B—C4B	1.384 (3)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.391 (3)	C4B—C5B	1.395 (3)
C4A—C8A	1.442 (3)	C4B—C8B	1.449 (3)
C5A—C6A	1.376 (3)	C5B—C6B	1.383 (3)
C6A—C7A	1.374 (3)	C6B—C7B	1.374 (3)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C9A	1.327 (3)	C8B—C9B	1.316 (3)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.484 (3)	C9B—C10B	1.491 (3)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.563 (3)	C10B—C11B	1.564 (3)
C11A—C14A	1.496 (3)	C11B—C14B	1.506 (3)
C11A—C12A	1.519 (3)	C11B—C12B	1.526 (3)
C11A—C13A	1.550 (3)	C11B—C13B	1.541 (3)
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
C14A—C15A	1.370 (3)	C14B—C19B	1.379 (3)
C14A—C19A	1.388 (3)	C14B—C15B	1.384 (3)
C15A—C16A	1.391 (3)	C19B—C18B	1.392 (3)
C15A—H15A	0.9300	C18B—C17B	1.367 (4)
C16A—C17A	1.363 (4)	C18B—H18B	0.9300
C16A—H16A	0.9300	C17B—C16B	1.359 (4)
C17A—C18A	1.373 (3)	C17B—H17B	0.9300
C17A—H17A	0.9300	C15B—C16B	1.388 (4)
C18A—C19A	1.389 (3)	C15B—H15B	0.9300
C18A—H18A	0.9300	C16B—H16B	0.9300
C20A—H20A	0.9600	C20B—H20D	0.9600
C20A—H20B	0.9600	C20B—H20E	0.9600
C20A—H20C	0.9600	C20B—H20F	0.9600
C5A—O2A—C10A	122.59 (15)	C5B—O2B—C10B	123.02 (15)
C19A—N1A—C10A	108.61 (18)	C19B—N1B—C10B	109.09 (18)
C19A—N1A—C20A	121.1 (2)	C19B—N1B—C20B	121.29 (19)
C10A—N1A—C20A	120.7 (2)	C10B—N1B—C20B	120.08 (18)
O1A—C1A—C2A	126.9 (2)	O1B—C1B—C2B	124.6 (2)
O1A—C1A—H1A	116.5	O1B—C1B—H1B	117.7
C2A—C1A—H1A	116.5	C2B—C1B—H1B	117.7
C3A—C2A—C7A	119.25 (18)	C3B—C2B—C7B	118.83 (18)
C3A—C2A—C1A	120.2 (2)	C3B—C2B—C1B	120.9 (2)
C7A—C2A—C1A	120.5 (2)	C7B—C2B—C1B	120.3 (2)
C2A—C3A—C4A	121.58 (18)	C4B—C3B—C2B	121.57 (19)
C2A—C3A—H3A	119.2	C4B—C3B—H3B	119.2
C4A—C3A—H3A	119.2	C2B—C3B—H3B	119.2
C3A—C4A—C5A	117.97 (19)	C3B—C4B—C5B	118.07 (18)
C3A—C4A—C8A	124.31 (17)	C3B—C4B—C8B	124.22 (18)
C5A—C4A—C8A	117.66 (18)	C5B—C4B—C8B	117.71 (17)
O2A—C5A—C6A	116.54 (17)	O2B—C5B—C6B	117.10 (17)
O2A—C5A—C4A	122.31 (18)	O2B—C5B—C4B	121.59 (17)
C6A—C5A—C4A	121.14 (18)	C6B—C5B—C4B	121.28 (17)
C7A—C6A—C5A	119.86 (19)	C7B—C6B—C5B	119.33 (18)
C7A—C6A—H6A	120.1	C7B—C6B—H6B	120.3
C5A—C6A—H6A	120.1	C5B—C6B—H6B	120.3
C6A—C7A—C2A	120.2 (2)	C6B—C7B—C2B	120.88 (19)
C6A—C7A—H7A	119.9	C6B—C7B—H7B	119.6
C2A—C7A—H7A	119.9	C2B—C7B—H7B	119.6
C9A—C8A—C4A	121.26 (19)	C9B—C8B—C4B	121.27 (19)
C9A—C8A—H8A	119.4	C9B—C8B—H8B	119.4
C4A—C8A—H8A	119.4	C4B—C8B—H8B	119.4
C8A—C9A—C10A	123.9 (2)	C8B—C9B—C10B	123.9 (2)
C8A—C9A—H9A	118.1	C8B—C9B—H9B	118.0
C10A—C9A—H9A	118.1	C10B—C9B—H9B	118.0
N1A—C10A—O2A	106.42 (18)	N1B—C10B—O2B	108.15 (16)
N1A—C10A—C9A	112.9 (2)	N1B—C10B—C9B	111.37 (19)
O2A—C10A—C9A	111.73 (16)	O2B—C10B—C9B	111.34 (15)
N1A—C10A—C11A	102.91 (15)	N1B—C10B—C11B	103.37 (15)
O2A—C10A—C11A	107.16 (17)	O2B—C10B—C11B	105.35 (17)
C9A—C10A—C11A	115.0 (2)	C9B—C10B—C11B	116.6 (2)
C14A—C11A—C12A	114.86 (18)	C14B—C11B—C12B	114.2 (2)
C14A—C11A—C13A	108.46 (16)	C14B—C11B—C13B	107.99 (17)
C12A—C11A—C13A	108.8 (2)	C12B—C11B—C13B	109.9 (2)
C14A—C11A—C10A	101.05 (18)	C14B—C11B—C10B	101.05 (18)
C12A—C11A—C10A	113.24 (18)	C12B—C11B—C10B	112.57 (18)
C13A—C11A—C10A	110.13 (17)	C13B—C11B—C10B	110.9 (2)
C11A—C12A—H12A	109.5	C11B—C12B—H12D	109.5
C11A—C12A—H12B	109.5	C11B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C11A—C12A—H12C	109.5	C11B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C15A—C14A—C19A	119.6 (2)	C19B—C14B—C15B	118.9 (2)
C15A—C14A—C11A	131.2 (2)	C19B—C14B—C11B	109.29 (19)
C19A—C14A—C11A	109.06 (18)	C15B—C14B—C11B	131.5 (2)
C14A—C15A—C16A	119.9 (2)	C14B—C19B—N1B	110.14 (19)
C14A—C15A—H15A	120.1	C14B—C19B—C18B	121.5 (2)
C16A—C15A—H15A	120.1	N1B—C19B—C18B	128.2 (2)
C17A—C16A—C15A	119.4 (2)	C17B—C18B—C19B	118.1 (3)
C17A—C16A—H16A	120.3	C17B—C18B—H18B	120.9
C15A—C16A—H16A	120.3	C19B—C18B—H18B	120.9
C16A—C17A—C18A	122.3 (2)	C16B—C17B—C18B	121.5 (3)
C16A—C17A—H17A	118.8	C16B—C17B—H17B	119.3
C18A—C17A—H17A	118.8	C18B—C17B—H17B	119.3
C17A—C18A—C19A	117.7 (3)	C16B—C15B—C14B	119.5 (3)
C17A—C18A—H18A	121.2	C16B—C15B—H15B	120.3
C19A—C18A—H18A	121.2	C14B—C15B—H15B	120.3
C14A—C19A—C18A	121.1 (2)	C17B—C16B—C15B	120.4 (3)
C14A—C19A—N1A	109.65 (19)	C17B—C16B—H16B	119.8
C18A—C19A—N1A	129.2 (2)	C15B—C16B—H16B	119.8
N1A—C20A—H20A	109.5	N1B—C20B—H20D	109.5
N1A—C20A—H20B	109.5	N1B—C20B—H20E	109.5
H20A—C20A—H20B	109.5	H20D—C20B—H20E	109.5
N1A—C20A—H20C	109.5	N1B—C20B—H20F	109.5
H20A—C20A—H20C	109.5	H20D—C20B—H20F	109.5
H20B—C20A—H20C	109.5	H20E—C20B—H20F	109.5
O1A—C1A—C2A—C3A	−177.2 (3)	O1B—C1B—C2B—C3B	−4.8 (4)
O1A—C1A—C2A—C7A	2.2 (4)	O1B—C1B—C2B—C7B	173.7 (2)
C7A—C2A—C3A—C4A	−0.4 (3)	C7B—C2B—C3B—C4B	−0.7 (3)
C1A—C2A—C3A—C4A	179.0 (2)	C1B—C2B—C3B—C4B	177.8 (2)
C2A—C3A—C4A—C5A	1.0 (3)	C2B—C3B—C4B—C5B	−1.2 (3)
C2A—C3A—C4A—C8A	−176.2 (2)	C2B—C3B—C4B—C8B	178.9 (2)
C10A—O2A—C5A—C6A	177.3 (2)	C10B—O2B—C5B—C6B	−173.19 (19)
C10A—O2A—C5A—C4A	−3.5 (3)	C10B—O2B—C5B—C4B	8.8 (3)
C3A—C4A—C5A—O2A	−179.6 (2)	C3B—C4B—C5B—O2B	−179.71 (19)
C8A—C4A—C5A—O2A	−2.3 (3)	C8B—C4B—C5B—O2B	0.2 (3)
C3A—C4A—C5A—C6A	−0.6 (3)	C3B—C4B—C5B—C6B	2.4 (3)
C8A—C4A—C5A—C6A	176.8 (2)	C8B—C4B—C5B—C6B	−177.7 (2)
O2A—C5A—C6A—C7A	178.7 (2)	O2B—C5B—C6B—C7B	−179.66 (18)
C4A—C5A—C6A—C7A	−0.5 (4)	C4B—C5B—C6B—C7B	−1.7 (3)
C5A—C6A—C7A—C2A	1.1 (4)	C5B—C6B—C7B—C2B	−0.3 (3)
C3A—C2A—C7A—C6A	−0.6 (4)	C3B—C2B—C7B—C6B	1.4 (3)
C1A—C2A—C7A—C6A	180.0 (2)	C1B—C2B—C7B—C6B	−177.1 (2)
C3A—C4A—C8A—C9A	179.7 (2)	C3B—C4B—C8B—C9B	175.9 (2)
C5A—C4A—C8A—C9A	2.5 (4)	C5B—C4B—C8B—C9B	−4.0 (3)
C4A—C8A—C9A—C10A	3.1 (4)	C4B—C8B—C9B—C10B	−1.2 (4)
C19A—N1A—C10A—O2A	84.07 (19)	C19B—N1B—C10B—O2B	85.19 (19)
C20A—N1A—C10A—O2A	−62.3 (3)	C20B—N1B—C10B—O2B	−61.5 (2)
C19A—N1A—C10A—C9A	−153.01 (19)	C19B—N1B—C10B—C9B	−152.16 (18)
C20A—N1A—C10A—C9A	60.6 (3)	C20B—N1B—C10B—C9B	61.2 (3)
C19A—N1A—C10A—C11A	−28.5 (2)	C19B—N1B—C10B—C11B	−26.2 (2)
C20A—N1A—C10A—C11A	−174.8 (2)	C20B—N1B—C10B—C11B	−172.83 (19)
C5A—O2A—C10A—N1A	131.9 (2)	C5B—O2B—C10B—N1B	109.9 (2)
C5A—O2A—C10A—C9A	8.3 (3)	C5B—O2B—C10B—C9B	−12.7 (3)
C5A—O2A—C10A—C11A	−118.5 (2)	C5B—O2B—C10B—C11B	−140.04 (19)
C8A—C9A—C10A—N1A	−128.0 (3)	C8B—C9B—C10B—N1B	−111.9 (3)
C8A—C9A—C10A—O2A	−8.1 (4)	C8B—C9B—C10B—O2B	8.9 (3)
C8A—C9A—C10A—C11A	114.3 (3)	C8B—C9B—C10B—C11B	129.8 (3)
N1A—C10A—C11A—C14A	27.63 (19)	N1B—C10B—C11B—C14B	24.4 (2)
O2A—C10A—C11A—C14A	−84.35 (18)	O2B—C10B—C11B—C14B	−88.97 (18)
C9A—C10A—C11A—C14A	150.80 (19)	C9B—C10B—C11B—C14B	146.99 (19)
N1A—C10A—C11A—C12A	151.00 (19)	N1B—C10B—C11B—C12B	146.6 (2)
O2A—C10A—C11A—C12A	39.0 (2)	O2B—C10B—C11B—C12B	33.2 (3)
C9A—C10A—C11A—C12A	−85.8 (2)	C9B—C10B—C11B—C12B	−90.8 (3)
N1A—C10A—C11A—C13A	−86.9 (2)	N1B—C10B—C11B—C13B	−89.8 (2)
O2A—C10A—C11A—C13A	161.11 (16)	O2B—C10B—C11B—C13B	156.75 (17)
C9A—C10A—C11A—C13A	36.3 (3)	C9B—C10B—C11B—C13B	32.7 (3)
C12A—C11A—C14A—C15A	44.1 (3)	C12B—C11B—C14B—C19B	−136.6 (2)
C13A—C11A—C14A—C15A	−77.9 (3)	C13B—C11B—C14B—C19B	100.9 (2)
C10A—C11A—C14A—C15A	166.3 (2)	C10B—C11B—C14B—C19B	−15.5 (2)
C12A—C11A—C14A—C19A	−140.6 (2)	C12B—C11B—C14B—C15B	49.2 (3)
C13A—C11A—C14A—C19A	97.4 (2)	C13B—C11B—C14B—C15B	−73.3 (3)
C10A—C11A—C14A—C19A	−18.4 (2)	C10B—C11B—C14B—C15B	170.3 (2)
C19A—C14A—C15A—C16A	−0.8 (3)	C15B—C14B—C19B—N1B	175.22 (18)
C11A—C14A—C15A—C16A	174.1 (2)	C11B—C14B—C19B—N1B	0.2 (2)
C14A—C15A—C16A—C17A	0.6 (4)	C15B—C14B—C19B—C18B	−1.1 (3)
C15A—C16A—C17A—C18A	0.2 (4)	C11B—C14B—C19B—C18B	−176.14 (19)
C16A—C17A—C18A—C19A	−0.9 (4)	C10B—N1B—C19B—C14B	17.2 (2)
C15A—C14A—C19A—C18A	0.1 (3)	C20B—N1B—C19B—C14B	163.4 (2)
C11A—C14A—C19A—C18A	−175.87 (19)	C10B—N1B—C19B—C18B	−166.8 (2)
C15A—C14A—C19A—N1A	177.72 (18)	C20B—N1B—C19B—C18B	−20.6 (3)
C11A—C14A—C19A—N1A	1.8 (2)	C14B—C19B—C18B—C17B	1.0 (3)
C17A—C18A—C19A—C14A	0.7 (3)	N1B—C19B—C18B—C17B	−174.6 (2)
C17A—C18A—C19A—N1A	−176.4 (2)	C19B—C18B—C17B—C16B	−0.2 (4)
C10A—N1A—C19A—C14A	17.8 (2)	C19B—C14B—C15B—C16B	0.5 (3)
C20A—N1A—C19A—C14A	164.0 (2)	C11B—C14B—C15B—C16B	174.2 (2)
C10A—N1A—C19A—C18A	−164.9 (2)	C18B—C17B—C16B—C15B	−0.3 (4)
C20A—N1A—C19A—C18A	−18.7 (4)	C14B—C15B—C16B—C17B	0.2 (4)

(I_Cc) 1',3',3'-trimethylspiro[2'H-1-benzopyran-2,2'-indoline]-6-carbaldehyde

Crystal data

C20H19NO2	F(000) = 1296
Mr = 305.36	Dx = 1.243 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3372 reflections
a = 11.699 (2) Å	θ = 1.7–27.9°
b = 11.692 (2) Å	µ = 0.08 mm^−1
c = 24.406 (5) Å	T = 293 K
β = 102.13 (3)°	Prism, white transparent
V = 3263.8 (10) Å^3	0.04 × 0.03 × 0.03 mm
Z = 8

Data collection

Nonius Kappa CCD diffractometer	3405 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.050
Graphite monochromator	θmax = 25.1°, θmin = 1.7°
Detector resolution: 95 pixels mm^-1	h = −13→13
ϕ and ω scans	k = −13→13
12585 measured reflections	l = −29→29
5001 independent 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)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.091	w = 1/[σ^2(Fo^2) + (0.0554P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.95	(Δ/σ)max = 0.002
2878 reflections	Δρmax = 0.12 e Å^−3
422 parameters	Δρmin = −0.13 e Å^−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0063 (7)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1A	0.9088 (2)	0.4017 (3)	0.37760 (12)	0.0853 (9)
O2A	0.36444 (18)	0.3221 (2)	0.27965 (8)	0.0542 (6)
N1A	0.1977 (2)	0.2622 (2)	0.30947 (11)	0.0542 (7)
C1A	0.8511 (3)	0.3796 (3)	0.33103 (17)	0.0650 (10)
H1A	0.8899	0.3751	0.3015	0.078*
C2A	0.7242 (3)	0.3597 (3)	0.31855 (13)	0.0520 (9)
C3A	0.6616 (3)	0.3600 (3)	0.36101 (13)	0.0514 (9)
H3A	0.7013	0.3687	0.3980	0.062*
C4A	0.5416 (3)	0.3478 (3)	0.34939 (12)	0.0466 (8)
C5A	0.4840 (3)	0.3343 (3)	0.29364 (12)	0.0458 (8)
C6A	0.5452 (3)	0.3303 (3)	0.25110 (13)	0.0531 (9)
H6A	0.5059	0.3192	0.2142	0.064*
C7A	0.6651 (3)	0.3428 (3)	0.26380 (13)	0.0560 (9)
H7A	0.7067	0.3398	0.2353	0.067*
C8A	0.4720 (3)	0.3466 (3)	0.39220 (13)	0.0595 (10)
H8A	0.5092	0.3475	0.4298	0.071*
C9A	0.3566 (3)	0.3442 (3)	0.37842 (13)	0.0624 (10)
H9A	0.3155	0.3404	0.4071	0.075*
C10A	0.2886 (3)	0.3473 (3)	0.31955 (12)	0.0469 (8)
C11A	0.2218 (3)	0.4610 (3)	0.30049 (12)	0.0515 (8)
C12A	0.2986 (4)	0.5478 (3)	0.27834 (18)	0.0771 (11)
H12A	0.3608	0.5719	0.3083	0.116*
H12B	0.2523	0.6128	0.2635	0.116*
H12C	0.3309	0.5132	0.2493	0.116*
C13A	0.1747 (4)	0.5146 (3)	0.34909 (16)	0.0716 (11)
H13A	0.2390	0.5396	0.3778	0.107*
H13B	0.1299	0.4587	0.3643	0.107*
H13C	0.1258	0.5788	0.3354	0.107*
C19A	0.1091 (3)	0.2998 (3)	0.26586 (12)	0.0516 (8)
C18A	0.0183 (3)	0.2362 (4)	0.23463 (15)	0.0721 (11)
H18A	0.0123	0.1580	0.2405	0.086*
C17A	−0.0621 (4)	0.2919 (6)	0.19506 (18)	0.0922 (15)
H17A	−0.1243	0.2508	0.1741	0.111*
C16A	−0.0539 (4)	0.4061 (6)	0.18533 (16)	0.0899 (15)
H16A	−0.1089	0.4412	0.1573	0.108*
C15A	0.0372 (4)	0.4709 (4)	0.21741 (15)	0.0771 (12)
H15A	0.0422	0.5492	0.2115	0.092*
C14A	0.1194 (3)	0.4162 (3)	0.25794 (12)	0.0519 (8)
C20A	0.2286 (4)	0.1418 (3)	0.31491 (18)	0.0829 (13)
H20A	0.2892	0.1306	0.3477	0.124*
H20B	0.2559	0.1173	0.2824	0.124*
H20C	0.1611	0.0978	0.3182	0.124*
O1B	0.1590 (3)	0.7190 (3)	0.12625 (13)	0.0968 (10)
O2B	0.15210 (19)	0.2171 (2)	0.02426 (8)	0.0544 (6)
N1B	0.2301 (2)	0.0354 (3)	0.04624 (11)	0.0579 (7)
C1B	0.1351 (3)	0.6808 (4)	0.07959 (19)	0.0722 (11)
H1B	0.1085	0.7320	0.0506	0.087*
C2B	0.1442 (3)	0.5605 (3)	0.06449 (13)	0.0547 (9)
C3B	0.1856 (3)	0.4798 (3)	0.10620 (13)	0.0551 (9)
H3B	0.2115	0.5044	0.1430	0.066*
C4B	0.1891 (3)	0.3650 (3)	0.09425 (12)	0.0495 (8)
C5B	0.1516 (3)	0.3298 (3)	0.03872 (12)	0.0469 (8)
C6B	0.1135 (3)	0.4084 (3)	−0.00392 (12)	0.0543 (9)
H6B	0.0905	0.3840	−0.0409	0.065*
C7B	0.1102 (3)	0.5227 (3)	0.00922 (14)	0.0575 (9)
H7B	0.0848	0.5756	−0.0192	0.069*
C8B	0.2329 (3)	0.2787 (4)	0.13594 (12)	0.0606 (10)
H8B	0.2668	0.3009	0.1723	0.073*
C9B	0.2254 (3)	0.1690 (4)	0.12306 (13)	0.0607 (10)
H9B	0.2589	0.1165	0.1503	0.073*
C10B	0.1657 (3)	0.1250 (3)	0.06689 (13)	0.0504 (9)
C11B	0.0437 (3)	0.0691 (3)	0.06482 (13)	0.0506 (8)
C12B	−0.0555 (3)	0.1571 (3)	0.05451 (16)	0.0664 (10)
H12D	−0.0412	0.2137	0.0837	0.100*
H12E	−0.1284	0.1193	0.0545	0.100*
H12F	−0.0591	0.1934	0.0189	0.100*
C13B	0.0423 (4)	0.0025 (3)	0.11911 (14)	0.0723 (11)
H13D	0.0531	0.0547	0.1501	0.109*
H13E	0.1043	−0.0528	0.1254	0.109*
H13F	−0.0314	−0.0359	0.1157	0.109*
C14B	0.0391 (3)	−0.0162 (3)	0.01754 (12)	0.0498 (8)
C15B	−0.0528 (3)	−0.0781 (3)	−0.01253 (14)	0.0621 (10)
H15B	−0.1276	−0.0692	−0.0057	0.074*
C16B	−0.0327 (4)	−0.1539 (3)	−0.05314 (16)	0.0721 (11)
H16B	−0.0944	−0.1960	−0.0738	0.087*
C17B	0.0772 (4)	−0.1671 (4)	−0.06288 (15)	0.0768 (12)
H17B	0.0890	−0.2171	−0.0908	0.092*
C18B	0.1712 (4)	−0.1079 (3)	−0.03230 (15)	0.0698 (10)
H18B	0.2460	−0.1184	−0.0387	0.084*
C19B	0.1506 (3)	−0.0320 (3)	0.00844 (12)	0.0524 (9)
C20B	0.3474 (3)	0.0569 (4)	0.03802 (17)	0.0823 (12)
H20D	0.3889	0.1033	0.0681	0.123*
H20E	0.3433	0.0960	0.0031	0.123*
H20F	0.3876	−0.0145	0.0374	0.123*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0591 (17)	0.103 (2)	0.090 (2)	0.0002 (16)	0.0068 (14)	0.0132 (16)
O2A	0.0517 (15)	0.0700 (16)	0.0410 (11)	0.0034 (11)	0.0103 (10)	−0.0045 (10)
N1A	0.0582 (18)	0.0408 (18)	0.0661 (16)	−0.0033 (13)	0.0188 (14)	0.0031 (13)
C1A	0.059 (3)	0.059 (3)	0.079 (3)	0.0088 (19)	0.020 (2)	0.0120 (19)
C2A	0.050 (2)	0.045 (2)	0.061 (2)	0.0073 (16)	0.0128 (17)	0.0023 (15)
C3A	0.051 (2)	0.051 (2)	0.0502 (18)	0.0081 (17)	0.0066 (15)	0.0021 (15)
C4A	0.047 (2)	0.047 (2)	0.0445 (18)	0.0034 (15)	0.0066 (14)	0.0013 (13)
C5A	0.049 (2)	0.044 (2)	0.0448 (18)	0.0041 (15)	0.0089 (15)	−0.0011 (13)
C6A	0.061 (3)	0.058 (2)	0.0429 (17)	0.0026 (17)	0.0159 (16)	−0.0032 (14)
C7A	0.065 (3)	0.048 (2)	0.062 (2)	0.0088 (18)	0.0294 (18)	0.0023 (16)
C8A	0.058 (3)	0.080 (3)	0.0393 (17)	0.0043 (19)	0.0093 (15)	−0.0031 (15)
C9A	0.057 (3)	0.087 (3)	0.0455 (19)	0.0003 (19)	0.0146 (16)	0.0013 (16)
C10A	0.0475 (19)	0.053 (2)	0.0432 (17)	0.0015 (16)	0.0155 (13)	−0.0018 (14)
C11A	0.058 (2)	0.042 (2)	0.0585 (18)	−0.0020 (17)	0.0212 (16)	−0.0020 (15)
C12A	0.080 (3)	0.053 (3)	0.103 (3)	−0.012 (2)	0.032 (2)	0.005 (2)
C13A	0.070 (3)	0.061 (3)	0.085 (3)	0.000 (2)	0.0208 (19)	−0.0223 (19)
C19A	0.043 (2)	0.061 (3)	0.0529 (19)	−0.0029 (17)	0.0164 (15)	−0.0075 (16)
C18A	0.063 (3)	0.089 (3)	0.070 (2)	−0.019 (2)	0.026 (2)	−0.029 (2)
C17A	0.058 (3)	0.152 (5)	0.067 (3)	−0.009 (3)	0.015 (2)	−0.037 (3)
C16A	0.062 (3)	0.149 (5)	0.056 (2)	0.025 (3)	0.0063 (19)	0.002 (3)
C15A	0.070 (3)	0.093 (3)	0.071 (3)	0.024 (3)	0.021 (2)	0.016 (2)
C14A	0.047 (2)	0.057 (3)	0.0547 (18)	0.0068 (17)	0.0169 (15)	0.0019 (16)
C20A	0.112 (4)	0.042 (3)	0.101 (3)	0.010 (2)	0.037 (3)	0.0093 (19)
O1B	0.112 (2)	0.070 (2)	0.097 (2)	0.0028 (18)	−0.0041 (17)	−0.0178 (17)
O2B	0.0601 (15)	0.0579 (17)	0.0451 (11)	−0.0045 (12)	0.0104 (10)	0.0001 (11)
N1B	0.0416 (17)	0.067 (2)	0.0668 (17)	0.0045 (15)	0.0162 (13)	−0.0011 (15)
C1B	0.064 (3)	0.065 (3)	0.086 (3)	−0.004 (2)	0.010 (2)	0.003 (2)
C2B	0.0429 (19)	0.059 (2)	0.062 (2)	−0.0068 (16)	0.0108 (16)	0.0024 (18)
C3B	0.045 (2)	0.065 (3)	0.0537 (19)	−0.0102 (17)	0.0048 (14)	−0.0028 (17)
C4B	0.0411 (18)	0.059 (3)	0.0471 (18)	−0.0066 (16)	0.0066 (13)	0.0007 (16)
C5B	0.0369 (18)	0.054 (2)	0.0503 (19)	−0.0065 (15)	0.0111 (13)	0.0013 (16)
C6B	0.049 (2)	0.073 (3)	0.0415 (17)	−0.0056 (18)	0.0095 (14)	0.0054 (17)
C7B	0.048 (2)	0.063 (3)	0.063 (2)	−0.0059 (18)	0.0141 (15)	0.0152 (18)
C8B	0.062 (2)	0.073 (3)	0.0413 (18)	−0.0052 (19)	−0.0014 (15)	0.0024 (17)
C9B	0.063 (2)	0.063 (3)	0.0520 (19)	0.0001 (19)	0.0011 (16)	0.0091 (17)
C10B	0.054 (2)	0.053 (2)	0.0444 (16)	0.0045 (17)	0.0123 (14)	0.0052 (15)
C11B	0.0466 (19)	0.055 (2)	0.0535 (17)	−0.0017 (16)	0.0182 (13)	0.0010 (15)
C12B	0.055 (2)	0.073 (3)	0.076 (2)	0.011 (2)	0.0258 (17)	−0.0040 (19)
C13B	0.092 (3)	0.074 (3)	0.058 (2)	−0.001 (2)	0.0315 (19)	0.0052 (18)
C14B	0.048 (2)	0.052 (2)	0.0505 (18)	0.0047 (17)	0.0142 (15)	0.0051 (15)
C15B	0.055 (2)	0.066 (3)	0.065 (2)	−0.0009 (19)	0.0120 (17)	0.0038 (18)
C16B	0.085 (3)	0.058 (3)	0.071 (2)	−0.007 (2)	0.011 (2)	−0.0070 (19)
C17B	0.108 (4)	0.062 (3)	0.060 (2)	0.006 (2)	0.018 (2)	−0.0111 (18)
C18B	0.081 (3)	0.063 (3)	0.072 (2)	0.017 (2)	0.032 (2)	0.002 (2)
C19B	0.057 (2)	0.051 (2)	0.0518 (18)	0.0075 (18)	0.0184 (16)	0.0048 (15)
C20B	0.046 (2)	0.107 (4)	0.098 (3)	−0.002 (2)	0.0237 (19)	0.003 (2)

Geometric parameters (Å, º)

O1A—C1A	1.222 (4)	O1B—C1B	1.200 (5)
O2A—C5A	1.376 (4)	O2B—C5B	1.365 (4)
O2A—C10A	1.479 (4)	O2B—C10B	1.482 (4)
N1A—C19A	1.392 (4)	N1B—C19B	1.406 (4)
N1A—C10A	1.439 (4)	N1B—C10B	1.442 (4)
N1A—C20A	1.453 (5)	N1B—C20B	1.450 (5)
C1A—C2A	1.469 (5)	C1B—C2B	1.463 (5)
C1A—H1A	0.9300	C1B—H1B	0.9300
C2A—C7A	1.384 (4)	C2B—C7B	1.395 (5)
C2A—C3A	1.389 (5)	C2B—C3B	1.398 (5)
C3A—C4A	1.380 (4)	C3B—C4B	1.376 (5)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.395 (4)	C4B—C5B	1.396 (4)
C4A—C8A	1.453 (5)	C4B—C8B	1.448 (5)
C5A—C6A	1.380 (4)	C5B—C6B	1.389 (5)
C6A—C7A	1.380 (5)	C6B—C7B	1.378 (5)
C6A—H6A	0.9300	C6B—H6B	0.9300
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—C9A	1.321 (5)	C8B—C9B	1.319 (5)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.489 (4)	C9B—C10B	1.493 (5)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.562 (5)	C10B—C11B	1.561 (5)
C11A—C14A	1.506 (5)	C11B—C14B	1.518 (5)
C11A—C12A	1.527 (5)	C11B—C12B	1.531 (5)
C11A—C13A	1.542 (5)	C11B—C13B	1.540 (5)
C12A—H12A	0.9600	C12B—H12D	0.9600
C12A—H12B	0.9600	C12B—H12E	0.9600
C12A—H12C	0.9600	C12B—H12F	0.9600
C13A—H13A	0.9600	C13B—H13D	0.9600
C13A—H13B	0.9600	C13B—H13E	0.9600
C13A—H13C	0.9600	C13B—H13F	0.9600
C19A—C14A	1.382 (5)	C14B—C15B	1.374 (5)
C19A—C18A	1.387 (5)	C14B—C19B	1.381 (5)
C18A—C17A	1.363 (6)	C15B—C16B	1.387 (5)
C18A—H18A	0.9300	C15B—H15B	0.9300
C17A—C16A	1.363 (7)	C16B—C17B	1.365 (6)
C17A—H17A	0.9300	C16B—H16B	0.9300
C16A—C15A	1.405 (7)	C17B—C18B	1.378 (6)
C16A—H16A	0.9300	C17B—H17B	0.9300
C15A—C14A	1.383 (5)	C18B—C19B	1.391 (5)
C15A—H15A	0.9300	C18B—H18B	0.9300
C20A—H20A	0.9600	C20B—H20D	0.9600
C20A—H20B	0.9600	C20B—H20E	0.9600
C20A—H20C	0.9600	C20B—H20F	0.9600
C5A—O2A—C10A	122.4 (2)	C5B—O2B—C10B	121.7 (2)
C19A—N1A—C10A	108.5 (3)	C19B—N1B—C10B	108.3 (3)
C19A—N1A—C20A	120.5 (3)	C19B—N1B—C20B	121.4 (3)
C10A—N1A—C20A	119.6 (3)	C10B—N1B—C20B	120.1 (3)
O1A—C1A—C2A	124.3 (4)	O1B—C1B—C2B	125.6 (4)
O1A—C1A—H1A	117.8	O1B—C1B—H1B	117.2
C2A—C1A—H1A	117.8	C2B—C1B—H1B	117.2
C7A—C2A—C3A	119.1 (3)	C7B—C2B—C3B	118.4 (3)
C7A—C2A—C1A	120.1 (3)	C7B—C2B—C1B	121.8 (3)
C3A—C2A—C1A	120.9 (3)	C3B—C2B—C1B	119.8 (3)
C4A—C3A—C2A	121.3 (3)	C4B—C3B—C2B	121.7 (3)
C4A—C3A—H3A	119.3	C4B—C3B—H3B	119.2
C2A—C3A—H3A	119.3	C2B—C3B—H3B	119.2
C3A—C4A—C5A	118.3 (3)	C3B—C4B—C5B	118.4 (3)
C3A—C4A—C8A	123.6 (3)	C3B—C4B—C8B	123.5 (3)
C5A—C4A—C8A	118.1 (3)	C5B—C4B—C8B	118.0 (3)
O2A—C5A—C6A	118.1 (3)	O2B—C5B—C6B	117.6 (3)
O2A—C5A—C4A	120.8 (3)	O2B—C5B—C4B	121.2 (3)
C6A—C5A—C4A	121.1 (3)	C6B—C5B—C4B	121.2 (3)
C7A—C6A—C5A	119.4 (3)	C7B—C6B—C5B	119.2 (3)
C7A—C6A—H6A	120.3	C7B—C6B—H6B	120.4
C5A—C6A—H6A	120.3	C5B—C6B—H6B	120.4
C6A—C7A—C2A	120.7 (3)	C6B—C7B—C2B	121.1 (3)
C6A—C7A—H7A	119.7	C6B—C7B—H7B	119.5
C2A—C7A—H7A	119.7	C2B—C7B—H7B	119.5
C9A—C8A—C4A	120.9 (3)	C9B—C8B—C4B	120.9 (3)
C9A—C8A—H8A	119.5	C9B—C8B—H8B	119.5
C4A—C8A—H8A	119.5	C4B—C8B—H8B	119.5
C8A—C9A—C10A	123.8 (3)	C8B—C9B—C10B	123.3 (3)
C8A—C9A—H9A	118.1	C8B—C9B—H9B	118.4
C10A—C9A—H9A	118.1	C10B—C9B—H9B	118.4
N1A—C10A—O2A	105.9 (2)	N1B—C10B—O2B	105.6 (2)
N1A—C10A—C9A	112.0 (3)	N1B—C10B—C9B	113.1 (3)
O2A—C10A—C9A	110.9 (3)	O2B—C10B—C9B	110.8 (3)
N1A—C10A—C11A	103.4 (3)	N1B—C10B—C11B	103.1 (3)
O2A—C10A—C11A	107.8 (2)	O2B—C10B—C11B	108.6 (2)
C9A—C10A—C11A	116.1 (3)	C9B—C10B—C11B	115.0 (3)
C14A—C11A—C12A	115.4 (3)	C14B—C11B—C12B	114.3 (3)
C14A—C11A—C13A	108.1 (3)	C14B—C11B—C13B	108.5 (3)
C12A—C11A—C13A	109.5 (3)	C12B—C11B—C13B	109.6 (3)
C14A—C11A—C10A	100.6 (3)	C14B—C11B—C10B	100.7 (2)
C12A—C11A—C10A	112.1 (3)	C12B—C11B—C10B	112.3 (3)
C13A—C11A—C10A	110.7 (3)	C13B—C11B—C10B	111.0 (3)
C11A—C12A—H12A	109.5	C11B—C12B—H12D	109.5
C11A—C12A—H12B	109.5	C11B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
C11A—C12A—H12C	109.5	C11B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C11A—C13A—H13A	109.5	C11B—C13B—H13D	109.5
C11A—C13A—H13B	109.5	C11B—C13B—H13E	109.5
H13A—C13A—H13B	109.5	H13D—C13B—H13E	109.5
C11A—C13A—H13C	109.5	C11B—C13B—H13F	109.5
H13A—C13A—H13C	109.5	H13D—C13B—H13F	109.5
H13B—C13A—H13C	109.5	H13E—C13B—H13F	109.5
C14A—C19A—C18A	122.0 (3)	C15B—C14B—C19B	120.2 (3)
C14A—C19A—N1A	110.2 (3)	C15B—C14B—C11B	130.6 (3)
C18A—C19A—N1A	127.7 (4)	C19B—C14B—C11B	109.1 (3)
C17A—C18A—C19A	117.9 (4)	C14B—C15B—C16B	119.2 (4)
C17A—C18A—H18A	121.1	C14B—C15B—H15B	120.4
C19A—C18A—H18A	121.1	C16B—C15B—H15B	120.4
C18A—C17A—C16A	121.9 (4)	C17B—C16B—C15B	120.3 (4)
C18A—C17A—H17A	119.0	C17B—C16B—H16B	119.9
C16A—C17A—H17A	119.0	C15B—C16B—H16B	119.9
C17A—C16A—C15A	120.3 (4)	C16B—C17B—C18B	121.5 (3)
C17A—C16A—H16A	119.9	C16B—C17B—H17B	119.2
C15A—C16A—H16A	119.9	C18B—C17B—H17B	119.2
C14A—C15A—C16A	118.8 (4)	C17B—C18B—C19B	118.0 (4)
C14A—C15A—H15A	120.6	C17B—C18B—H18B	121.0
C16A—C15A—H15A	120.6	C19B—C18B—H18B	121.0
C19A—C14A—C15A	119.2 (4)	C14B—C19B—C18B	120.8 (3)
C19A—C14A—C11A	109.0 (3)	C14B—C19B—N1B	109.7 (3)
C15A—C14A—C11A	131.7 (4)	C18B—C19B—N1B	129.5 (3)
N1A—C20A—H20A	109.5	N1B—C20B—H20D	109.5
N1A—C20A—H20B	109.5	N1B—C20B—H20E	109.5
H20A—C20A—H20B	109.5	H20D—C20B—H20E	109.5
N1A—C20A—H20C	109.5	N1B—C20B—H20F	109.5
H20A—C20A—H20C	109.5	H20D—C20B—H20F	109.5
H20B—C20A—H20C	109.5	H20E—C20B—H20F	109.5
O1A—C1A—C2A—C7A	175.6 (4)	O1B—C1B—C2B—C7B	177.5 (4)
O1A—C1A—C2A—C3A	−3.0 (6)	O1B—C1B—C2B—C3B	−1.2 (6)
C7A—C2A—C3A—C4A	−2.3 (5)	C7B—C2B—C3B—C4B	−2.6 (5)
C1A—C2A—C3A—C4A	176.3 (3)	C1B—C2B—C3B—C4B	176.1 (3)
C2A—C3A—C4A—C5A	0.3 (5)	C2B—C3B—C4B—C5B	1.0 (5)
C2A—C3A—C4A—C8A	179.5 (3)	C2B—C3B—C4B—C8B	179.1 (3)
C10A—O2A—C5A—C6A	−167.8 (3)	C10B—O2B—C5B—C6B	−166.3 (3)
C10A—O2A—C5A—C4A	13.7 (4)	C10B—O2B—C5B—C4B	14.3 (4)
C3A—C4A—C5A—O2A	−179.8 (3)	C3B—C4B—C5B—O2B	−179.5 (3)
C8A—C4A—C5A—O2A	1.0 (5)	C8B—C4B—C5B—O2B	2.3 (4)
C3A—C4A—C5A—C6A	1.7 (5)	C3B—C4B—C5B—C6B	1.2 (5)
C8A—C4A—C5A—C6A	−177.5 (3)	C8B—C4B—C5B—C6B	−177.0 (3)
O2A—C5A—C6A—C7A	179.7 (3)	O2B—C5B—C6B—C7B	179.1 (3)
C4A—C5A—C6A—C7A	−1.7 (5)	C4B—C5B—C6B—C7B	−1.6 (5)
C5A—C6A—C7A—C2A	−0.3 (5)	C5B—C6B—C7B—C2B	−0.1 (5)
C3A—C2A—C7A—C6A	2.2 (5)	C3B—C2B—C7B—C6B	2.1 (5)
C1A—C2A—C7A—C6A	−176.4 (3)	C1B—C2B—C7B—C6B	−176.5 (3)
C3A—C4A—C8A—C9A	174.3 (3)	C3B—C4B—C8B—C9B	174.4 (3)
C5A—C4A—C8A—C9A	−6.6 (5)	C5B—C4B—C8B—C9B	−7.5 (5)
C4A—C8A—C9A—C10A	−2.5 (6)	C4B—C8B—C9B—C10B	−4.0 (5)
C19A—N1A—C10A—O2A	−85.4 (3)	C19B—N1B—C10B—O2B	−83.9 (3)
C20A—N1A—C10A—O2A	58.2 (3)	C20B—N1B—C10B—O2B	61.8 (4)
C19A—N1A—C10A—C9A	153.6 (3)	C19B—N1B—C10B—C9B	154.7 (3)
C20A—N1A—C10A—C9A	−62.8 (4)	C20B—N1B—C10B—C9B	−59.5 (4)
C19A—N1A—C10A—C11A	27.8 (3)	C19B—N1B—C10B—C11B	29.9 (3)
C20A—N1A—C10A—C11A	171.4 (3)	C20B—N1B—C10B—C11B	175.7 (3)
C5A—O2A—C10A—N1A	−142.4 (3)	C5B—O2B—C10B—N1B	−146.3 (3)
C5A—O2A—C10A—C9A	−20.7 (4)	C5B—O2B—C10B—C9B	−23.4 (4)
C5A—O2A—C10A—C11A	107.4 (3)	C5B—O2B—C10B—C11B	103.7 (3)
C8A—C9A—C10A—N1A	133.3 (4)	C8B—C9B—C10B—N1B	136.8 (4)
C8A—C9A—C10A—O2A	15.2 (5)	C8B—C9B—C10B—O2B	18.4 (5)
C8A—C9A—C10A—C11A	−108.2 (4)	C8B—C9B—C10B—C11B	−105.1 (4)
N1A—C10A—C11A—C14A	−26.7 (3)	N1B—C10B—C11B—C14B	−27.7 (3)
O2A—C10A—C11A—C14A	85.2 (3)	O2B—C10B—C11B—C14B	84.0 (3)
C9A—C10A—C11A—C14A	−149.8 (3)	C9B—C10B—C11B—C14B	−151.3 (3)
N1A—C10A—C11A—C12A	−149.9 (3)	N1B—C10B—C11B—C12B	−149.8 (3)
O2A—C10A—C11A—C12A	−38.1 (4)	O2B—C10B—C11B—C12B	−38.1 (3)
C9A—C10A—C11A—C12A	87.0 (4)	C9B—C10B—C11B—C12B	86.6 (4)
N1A—C10A—C11A—C13A	87.4 (3)	N1B—C10B—C11B—C13B	87.0 (3)
O2A—C10A—C11A—C13A	−160.7 (3)	O2B—C10B—C11B—C13B	−161.3 (3)
C9A—C10A—C11A—C13A	−35.6 (4)	C9B—C10B—C11B—C13B	−36.5 (4)
C10A—N1A—C19A—C14A	−17.6 (3)	C12B—C11B—C14B—C15B	−45.6 (5)
C20A—N1A—C19A—C14A	−160.8 (3)	C13B—C11B—C14B—C15B	77.1 (4)
C10A—N1A—C19A—C18A	164.9 (3)	C10B—C11B—C14B—C15B	−166.3 (3)
C20A—N1A—C19A—C18A	21.7 (5)	C12B—C11B—C14B—C19B	137.8 (3)
C14A—C19A—C18A—C17A	0.2 (5)	C13B—C11B—C14B—C19B	−99.5 (3)
N1A—C19A—C18A—C17A	177.4 (3)	C10B—C11B—C14B—C19B	17.1 (3)
C19A—C18A—C17A—C16A	1.0 (6)	C19B—C14B—C15B—C16B	−1.8 (5)
C18A—C17A—C16A—C15A	−1.8 (7)	C11B—C14B—C15B—C16B	−178.1 (3)
C17A—C16A—C15A—C14A	1.4 (6)	C14B—C15B—C16B—C17B	0.2 (5)
C18A—C19A—C14A—C15A	−0.4 (5)	C15B—C16B—C17B—C18B	1.3 (6)
N1A—C19A—C14A—C15A	−178.1 (3)	C16B—C17B—C18B—C19B	−1.2 (6)
C18A—C19A—C14A—C11A	176.4 (3)	C15B—C14B—C19B—C18B	2.0 (5)
N1A—C19A—C14A—C11A	−1.3 (3)	C11B—C14B—C19B—C18B	179.0 (3)
C16A—C15A—C14A—C19A	−0.3 (5)	C15B—C14B—C19B—N1B	−176.5 (3)
C16A—C15A—C14A—C11A	−176.3 (3)	C11B—C14B—C19B—N1B	0.5 (4)
C12A—C11A—C14A—C19A	138.4 (3)	C17B—C18B—C19B—C14B	−0.4 (5)
C13A—C11A—C14A—C19A	−98.6 (3)	C17B—C18B—C19B—N1B	177.7 (3)
C10A—C11A—C14A—C19A	17.5 (3)	C10B—N1B—C19B—C14B	−20.0 (3)
C12A—C11A—C14A—C15A	−45.3 (5)	C20B—N1B—C19B—C14B	−165.3 (3)
C13A—C11A—C14A—C15A	77.7 (4)	C10B—N1B—C19B—C18B	161.7 (3)
C10A—C11A—C14A—C15A	−166.2 (3)	C20B—N1B—C19B—C18B	16.4 (5)