1,3,3 Trimeth­yl 6′ (4 phenyl­piperazin 1 yl) 2,3 di­hydro­spiro­[1H indole 2,3′ 3H naphth[2,1 b][1,4]oxazine]

(1)organic papers Acta Crystallographica Section E. Structure Reports Online ISSN 1600-5368. Hui Guo, Yong-Bin Gao, Yan-Xia Li, Jie Han and Ji-Ben Meng* Department of Chemistry, Nankai University, Tianjin 300071, People’s Republic of China. 1,3,3-Trimethyl-60 -(4-phenylpiperazin-1-yl)2,3-dihydrospiro[1H-indole-2,30 -3H-naphth[2,1-b][1,4]oxazine]. The title compound, C32H32N4O, a spirooxazine modified with a fused phenyl–piperazinyl–naphthalene moiety, has been characterized by X-ray crystallographic techniques. The piperazine ring is in a chair conformation, while the oxazine and pyrrolidine rings adopt envelope conformations.. Received 28 February 2005 Accepted 7 March 2005 Online 18 March 2005. Correspondence e-mail: mengjiben@nankai.edu.cn. Comment Key indicators Single-crystal X-ray study T = 273 K ˚ Mean (C–C) = 0.003 A R factor = 0.045 wR factor = 0.139 Data-to-parameter ratio = 13.6 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.. # 2005 International Union of Crystallography Printed in Great Britain – all rights reserved. o988. Guo et al.. . C32H32N4O. Spiropyrans and spirooxazines are important classes of photochromic materials (Winkler et al., 1998). Photochromic compounds continue to attract significant attention, in view of their general applicability as optical information storage materials or switching devices (Duerr, 1989; Dueer & BouasLaurent, 1990; Ichi, 2000), and also as organic photochromic materials within a plastic matrix, for example photochromic ophthalmic lenses and vehicle roof lights (Rickwood & Hepworth, 1990). Many modified spiropyrans and spirooxazines have been prepared in order to develop novel photochromic materials. The title compound, (I), is one of them. It becomes purple in sunlight, showing the suitability of the material for use in sun-lenses (Rickwood & Hepworth, 1990). Recently, our group has studied the synthesis and photochromic properties of certain spiropyrans and spirooxazines containing various functional groups (Li et al., 1999; Li, Li et al., 2000; Li, Wang et al., 2000; Chang et al., 2002; Zou et al., 2003). In the course of our studies, we obtained single crystals of (I) and we report its crystal structure here.. A perspective view of (I) with the atom-labelling scheme is shown in Fig. 1. The piperazine ring is in a chair conformation, while the oxazine and pyrrolidine rings adopt envelope conformations. Some of the bond angles at the spiro atom C11 deviate significantly from the normal value of 109.5 ; the angles lie in the range 103.73 (14)–115.08 (15) (Table 1). In the crystal packing of (I), inversion-related molecules are linked via C16—H16  (C27–C32)i interactions [symmetry code: (i) 1  x, 1  y, 1  z]. No other hydrogen bonds are observed in the crystal structure. However, the introduction of an ethoxycarbonyl group in the 60 -position of the indoline doi:10.1107/S1600536805007063. Acta Cryst. (2005). E61, o988–o989.

(2) organic papers moiety affects the whole arrangement of the molecular selfassembly. The carbonyl O atom is involved in hydrogen bonds, leading to the formation of a helical structure (Song et al., 2003).. Experimental Compound (I) was synthesized using a method based on the reaction of an -nitro--naphthol derivative with a 2-methyleneindole compound, as described by Ono et al. (1971). The crude product was purified by silica-gel column chromatography, using petroleum ether– ether (3:1 v/v) as eluant. Single crystals suitable for X-ray diffraction measurements were obtained from acetone by slow evaporation at room temperature.. The structure of (I), showing 30% probability displacement ellipsoids and the atom-labelling scheme.. Crystal data Dx = 1.248 Mg m3 Mo K radiation Cell parameters from 1853 reflections  = 2.7–22.1  = 0.08 mm1 T = 273 (2) K Block, colourless 0.34  0.24  0.16 mm. C32H32N4O Mr = 488.62 Monoclinic, P21 =c ˚ a = 15.359 (3) A ˚ b = 13.215 (3) A ˚ c = 12.969 (3) A  = 99.051 (3) ˚3 V = 2599.5 (9) A Z=4. All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the ˚ , and with Uiso(H) = 1.5Ueq(C) for methyl H atoms range 0.93–0.97 A and 1.2Ueq(C) for other H atoms. Methyl groups were allowed to rotate freely about the C—C bond. Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.. Data collection Bruker APEX CCD area-detector diffractometer ’ and ! scans Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.974, Tmax = 0.988 13 748 measured reflections. 4581 independent reflections 3018 reflections with I > 2(I) Rint = 0.037 max = 25.0 h = 18 ! 18 k = 15 ! 12 l = 15 ! 15. This work was supported financially by the National Science Foundation of China (grant Nos. 20372039 and 20402009). Refinement. References. Refinement on F 2 R[F 2 > 2(F 2)] = 0.045 wR(F 2) = 0.139 S = 1.06 4581 reflections 337 parameters H-atom parameters constrained. w = 1/[ 2(Fo2) + (0.0608P)2 + 0.1682P] where P = (Fo2 + 2Fc2)/3 (/)max = 0.001 ˚ 3 max = 0.17 e A ˚ 3 min = 0.16 e A. Table 1 ˚ ,  ). Selected geometric parameters (A O1—C22 O1—C11 N1—C2 N1—C11 N1—C1 N2—C12 N2—C13 C2—N1—C11 C2—N1—C1 C11—N1—C1 N1—C11—O1 N1—C11—C12. Figure 1. 1.367 1.465 1.404 1.436 1.455 1.272 1.411 107.83 119.73 118.73 106.18 112.78. (2) (2) (2) (2) (2) (2) (2). (14) (15) (15) (13) (15). Acta Cryst. (2005). E61, o988–o989. N3—C20 N3—C26 N3—C23 N4—C27 N4—C25 N4—C24 O1—C11—C12 N1—C11—C8 O1—C11—C8 C12—C11—C8. 1.417 1.450 1.456 1.410 1.456 1.457 109.15 103.73 109.46 115.08. (2) (2) (2) (2) (3) (3). (15) (14) (14) (15). Bruker (1998). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SAINT and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Chang, P., Meng, J. B., Li, X. L., Matsuura, T. & Wang, Y. M. (2002). J. Heterocycl. Chem. 39, 179–184. Dueer, H. & Bouas-Laurent, H. (1990). Photochromism: Molecules and Systems. Amsterdam: Elsevier. Duerr, H. (1989). Angew. Chem. Int. Ed. Engl. 28, 413–431. Ichi, M. K. (2000). Chem. Rev. 100, 1847–1873. Li, X. L., Li, J. L., Wang, Y. M., Matsuura, T. & Meng, J. B. (2000). Mol. Cryst. Liq. Cryst. 344, 295–300. Li, X. L., Wang, Y. M., Matsuura, T. & Meng, J. B. (1999). Heterocycles, 51, 2639–2651. Li, X. L., Wang, Y. M., Matsuura, T. & Meng, J. B. (2000). Mol. Cryst. Liq. Cryst. 344, 301–307. Ono, H., Oasada, T. & Kosuge, K. (1971). US Pat. 3578602. Rickwood, M. & Hepworth, J. D. (1990). Eur. Pat. 245020. Sheldrick, G. M. (1996). SADABS. University of Go¨ttingen, Germany. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany. Song, Z. Y., Ji, Q., Sun, R., Matsuura, T. & Meng, J. B. (2003). J. Mol. Struct. 655, 31–35. Winkler, J. D., Bowen, C. M. & Michelet, V. (1998). J. Am. Chem. Soc. 120, 3237–3242. Zou, W. X., Chen, P. L., Gao, Y. & Meng, J. B. (2003). Acta Cryst. E59, o337– o339.. Guo et al.. . C32H32N4O. o989.

(3) supporting information. supporting information Acta Cryst. (2005). E61, o988–o989. [https://doi.org/10.1107/S1600536805007063]. 1,3,3-Trimethyl-6′-(4-phenylpiperazin-1-yl)-2,3-dihydrospiro[1Hindole-2,3′-3H-naphth[2,1-b][1,4]oxazine] Hui Guo, Yong-Bin Gao, Yan-Xia Li, Jie Han and Ji-Ben Meng 6′-(4-Phenylpiperazin-1-yl)-1,3,3-trimethyl-2,3-dihydrospiro[1H- indole-2,3′-3H-naphth[2,1-b][1,4]oxazine] Crystal data C32H32N4O Mr = 488.62 Monoclinic, P21/c Hall symbol: -P 2ybc a = 15.359 (3) Å b = 13.215 (3) Å c = 12.969 (3) Å β = 99.051 (3)° V = 2599.5 (9) Å3 Z=4. F(000) = 1040 Dx = 1.248 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1853 reflections θ = 2.7–22.1° µ = 0.08 mm−1 T = 273 K Block, colourless 0.34 × 0.24 × 0.16 mm. Data collection Bruker APEX CCD area-detector diffractometer Radiation source: fine-focus sealed tube Graphite monochromator φ and ω scans Absorption correction: multi-scan (SADABS; Sheldrick, 1996) Tmin = 0.974, Tmax = 0.988. 13748 measured reflections 4581 independent reflections 3018 reflections with I > 2σ(I) Rint = 0.037 θmax = 25.0°, θmin = 2.0° h = −18→18 k = −15→12 l = −15→15. Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.045 wR(F2) = 0.139 S = 1.06 4581 reflections 337 parameters 0 restraints Primary atom site location: structure-invariant direct methods. Acta Cryst. (2005). E61, o988–o989. Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ2(Fo2) + (0.0608P)2 + 0.1682P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.001 Δρmax = 0.17 e Å−3 Δρmin = −0.16 e Å−3. sup-1.

(4) supporting information 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 (Å2). O1 N1 N2 N3 N4 C1 H1A H1B H1C C2 C3 H3 C4 H4 C5 H5 C6 H6 C7 C8 C9 H9A H9B H9C C10 H10A H10B H10C C11 C12 H12 C13 C14 C15 H15. x. y. z. Uiso*/Ueq. 0.06646 (8) −0.04345 (10) 0.09886 (11) 0.31739 (10) 0.40412 (11) 0.01382 (14) −0.0213 0.0533 0.0472 −0.10592 (12) −0.14256 (13) −0.1260 −0.20457 (15) −0.2304 −0.22913 (15) −0.2709 −0.19169 (14) −0.2080 −0.13033 (12) −0.08182 (13) −0.14298 (15) −0.1950 −0.1127 −0.1594 −0.04911 (15) −0.0111 −0.0170 −0.0985 −0.00567 (12) 0.03011 (13) −0.0008 0.14920 (12) 0.22010 (12) 0.23794 (13) 0.2024. 0.21331 (8) 0.14646 (11) 0.35749 (11) 0.32099 (11) 0.29443 (13) 0.07141 (15) 0.0229 0.1043 0.0375 0.11614 (13) 0.02173 (14) −0.0332 0.01151 (16) −0.0514 0.09199 (16) 0.0830 0.18669 (15) 0.2414 0.19842 (13) 0.29121 (13) 0.35095 (17) 0.3712 0.4099 0.3090 0.35960 (16) 0.3218 0.4154 0.3848 0.24029 (13) 0.30241 (14) 0.3006 0.35371 (13) 0.42289 (13) 0.50184 (14) 0.5094. 0.55741 (10) 0.64094 (12) 0.71722 (12) 0.40858 (12) 0.23157 (13) 0.69900 (17) 0.7292 0.7535 0.6527 0.55568 (15) 0.53366 (17) 0.5772 0.44503 (18) 0.4291 0.37966 (18) 0.3202 0.40240 (17) 0.3585 0.49044 (15) 0.53673 (15) 0.5980 (2) 0.5515 0.6284 0.6522 0.45660 (18) 0.4187 0.4916 0.4089 0.61384 (15) 0.70723 (15) 0.7634 0.63516 (14) 0.63433 (14) 0.70834 (15) 0.7596. 0.0476 (3) 0.0465 (4) 0.0494 (4) 0.0454 (4) 0.0553 (4) 0.0583 (6) 0.088* 0.088* 0.088* 0.0442 (5) 0.0545 (5) 0.065* 0.0646 (6) 0.078* 0.0664 (6) 0.080* 0.0587 (5) 0.070* 0.0463 (5) 0.0501 (5) 0.0773 (7) 0.116* 0.116* 0.116* 0.0709 (7) 0.106* 0.106* 0.106* 0.0451 (5) 0.0506 (5) 0.061* 0.0424 (4) 0.0425 (4) 0.0515 (5) 0.062*. Acta Cryst. (2005). E61, o988–o989. sup-2.

(5) supporting information C16 H16 C17 H17 C18 H18 C19 C20 C21 H21 C22 C23 H23A H23B C24 H24A H24B C25 H25A H25B C26 H26A H26B C27 C28 H28 C29 H29 C30 H30 C31 H31 C32 H32. 0.30583 (14) 0.3153 0.36184 (14) 0.4087 0.34818 (13) 0.3868 0.27638 (11) 0.25923 (12) 0.18994 (12) 0.1791 0.13506 (12) 0.30280 (13) 0.2927 0.2510 0.38218 (14) 0.3706 0.4323 0.40577 (15) 0.4585 0.4087 0.32584 (14) 0.2734 0.3317 0.47279 (14) 0.49206 (16) 0.4593 0.55888 (17) 0.5701 0.60812 (17) 0.6527 0.5909 (2) 0.6243 0.52491 (17) 0.5152. 0.56642 (15) 0.6191 0.55470 (15) 0.5992 0.47862 (14) 0.4706 0.41176 (12) 0.33148 (13) 0.26750 (13) 0.2155 0.27981 (12) 0.39263 (15) 0.4596 0.3730 0.39448 (16) 0.4395 0.4211 0.21672 (15) 0.2251 0.1507 0.22075 (14) 0.2047 0.1711 0.29090 (16) 0.37211 (19) 0.4313 0.3676 (2) 0.4237 0.2832 (2) 0.2804 0.2031 (2) 0.1445 0.20604 (19) 0.1496. 0.70571 (17) 0.7537 0.63157 (18) 0.6309 0.56035 (17) 0.5125 0.55781 (14) 0.48254 (14) 0.48520 (14) 0.4366 0.56074 (14) 0.32228 (16) 0.3485 0.2736 0.26702 (18) 0.2074 0.3141 0.31143 (18) 0.3628 0.2795 0.36581 (17) 0.3166 0.4215 0.17116 (16) 0.11144 (18) 0.1116 0.05138 (19) 0.0121 0.0487 (2) 0.0079 0.1069 (2) 0.1059 0.1676 (2) 0.2071. 0.0602 (6) 0.072* 0.0629 (6) 0.075* 0.0539 (5) 0.065* 0.0429 (4) 0.0426 (4) 0.0444 (5) 0.053* 0.0421 (4) 0.0567 (5) 0.068* 0.068* 0.0629 (6) 0.075* 0.075* 0.0606 (6) 0.073* 0.073* 0.0587 (6) 0.070* 0.070* 0.0560 (5) 0.0751 (7) 0.090* 0.0851 (8) 0.102* 0.0835 (8) 0.100* 0.0931 (9) 0.112* 0.0816 (8) 0.098*. Atomic displacement parameters (Å2). O1 N1 N2 N3 N4 C1 C2 C3 C4 C5. U11. U22. U33. U12. U13. U23. 0.0524 (8) 0.0516 (10) 0.0570 (10) 0.0492 (9) 0.0528 (10) 0.0645 (13) 0.0476 (11) 0.0665 (14) 0.0784 (16) 0.0680 (15). 0.0400 (7) 0.0400 (9) 0.0473 (9) 0.0414 (9) 0.0644 (11) 0.0495 (12) 0.0436 (11) 0.0425 (11) 0.0494 (13) 0.0637 (14). 0.0543 (8) 0.0498 (10) 0.0452 (10) 0.0471 (9) 0.0517 (10) 0.0614 (14) 0.0455 (11) 0.0575 (13) 0.0666 (15) 0.0644 (15). −0.0099 (6) −0.0037 (7) −0.0016 (8) −0.0010 (7) 0.0029 (8) 0.0001 (10) −0.0043 (8) −0.0069 (10) −0.0150 (11) −0.0089 (11). 0.0202 (7) 0.0139 (8) 0.0119 (8) 0.0124 (8) 0.0168 (9) 0.0111 (11) 0.0194 (9) 0.0193 (11) 0.0129 (13) 0.0011 (12). −0.0088 (6) 0.0035 (7) −0.0056 (7) 0.0002 (7) −0.0004 (8) 0.0109 (10) −0.0012 (8) 0.0004 (9) −0.0095 (11) −0.0066 (11). Acta Cryst. (2005). E61, o988–o989. sup-3.

(6) supporting information C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30 C31 C32. 0.0634 (14) 0.0481 (11) 0.0555 (12) 0.0734 (16) 0.0809 (16) 0.0493 (11) 0.0567 (13) 0.0475 (11) 0.0470 (11) 0.0573 (12) 0.0654 (14) 0.0568 (13) 0.0495 (12) 0.0431 (10) 0.0450 (11) 0.0506 (11) 0.0463 (11) 0.0523 (12) 0.0616 (13) 0.0670 (14) 0.0680 (14) 0.0505 (12) 0.0762 (16) 0.0867 (19) 0.0735 (17) 0.099 (2) 0.0860 (18). 0.0511 (12) 0.0407 (10) 0.0388 (10) 0.0621 (14) 0.0494 (12) 0.0392 (10) 0.0501 (11) 0.0408 (10) 0.0371 (10) 0.0456 (11) 0.0487 (12) 0.0510 (13) 0.0506 (12) 0.0373 (10) 0.0403 (10) 0.0391 (10) 0.0350 (10) 0.0620 (13) 0.0615 (14) 0.0498 (12) 0.0500 (12) 0.0716 (14) 0.0894 (17) 0.111 (2) 0.119 (2) 0.091 (2) 0.0729 (16). 0.0603 (14) 0.0521 (12) 0.0564 (12) 0.0951 (19) 0.0784 (16) 0.0504 (11) 0.0479 (12) 0.0391 (10) 0.0412 (10) 0.0491 (12) 0.0622 (14) 0.0774 (16) 0.0610 (13) 0.0462 (11) 0.0428 (11) 0.0449 (11) 0.0452 (11) 0.0581 (13) 0.0703 (15) 0.0694 (14) 0.0625 (14) 0.0465 (12) 0.0657 (15) 0.0651 (17) 0.0643 (16) 0.101 (2) 0.0969 (19). 0.0020 (10) −0.0009 (8) −0.0009 (8) 0.0139 (11) −0.0103 (11) −0.0025 (8) −0.0036 (9) −0.0011 (8) 0.0028 (8) −0.0013 (9) −0.0070 (10) −0.0158 (10) −0.0077 (9) −0.0013 (8) 0.0008 (8) −0.0043 (8) −0.0035 (8) 0.0121 (10) 0.0143 (10) 0.0026 (10) −0.0052 (10) −0.0002 (10) 0.0170 (13) 0.0075 (16) 0.0005 (16) 0.0098 (16) 0.0046 (13). 0.0062 (12) 0.0139 (10) 0.0098 (10) 0.0090 (14) −0.0002 (13) 0.0186 (9) 0.0165 (10) 0.0078 (9) 0.0001 (9) 0.0008 (10) −0.0034 (12) 0.0000 (12) 0.0065 (10) 0.0007 (9) 0.0081 (9) 0.0118 (9) 0.0078 (9) 0.0155 (10) 0.0251 (12) 0.0247 (12) 0.0243 (12) 0.0087 (10) 0.0293 (13) 0.0345 (15) 0.0318 (14) 0.0507 (19) 0.0485 (16). 0.0043 (10) −0.0010 (9) 0.0019 (9) −0.0224 (13) 0.0179 (11) −0.0015 (8) −0.0045 (9) −0.0009 (8) −0.0005 (8) −0.0061 (9) −0.0123 (10) −0.0060 (11) −0.0020 (10) 0.0020 (8) 0.0023 (8) −0.0056 (8) −0.0008 (8) 0.0142 (10) 0.0191 (11) −0.0006 (10) −0.0049 (10) −0.0076 (10) 0.0169 (13) 0.0166 (14) −0.0161 (15) −0.0126 (17) −0.0058 (14). Geometric parameters (Å, º) O1—C22 O1—C11 N1—C2 N1—C11 N1—C1 N2—C12 N2—C13 N3—C20 N3—C26 N3—C23 N4—C27 N4—C25 N4—C24 C1—H1A C1—H1B C1—H1C C2—C3 C2—C7. Acta Cryst. (2005). E61, o988–o989. 1.367 (2) 1.465 (2) 1.404 (2) 1.436 (2) 1.455 (2) 1.272 (2) 1.411 (2) 1.417 (2) 1.450 (2) 1.456 (2) 1.410 (2) 1.456 (3) 1.457 (3) 0.96 0.96 0.96 1.380 (3) 1.392 (3). C13—C22 C13—C14 C14—C15 C14—C19 C15—C16 C15—H15 C16—C17 C16—H16 C17—C18 C17—H17 C18—C19 C18—H18 C19—C20 C20—C21 C21—C22 C21—H21 C23—C24 C23—H23A. 1.366 (2) 1.423 (2) 1.415 (2) 1.423 (2) 1.352 (3) 0.93 1.396 (3) 0.93 1.359 (3) 0.93 1.410 (3) 0.93 1.438 (2) 1.364 (2) 1.399 (2) 0.93 1.509 (3) 0.97. sup-4.

(7) supporting information C3—C4 C3—H3 C4—C5 C4—H4 C5—C6 C5—H5 C6—C7 C6—H6 C7—C8 C8—C10 C8—C9 C8—C11 C9—H9A C9—H9B C9—H9C C10—H10A C10—H10B C10—H10C C11—C12 C12—H12. 1.379 (3) 0.93 1.375 (3) 0.93 1.389 (3) 0.93 1.370 (3) 0.93 1.509 (3) 1.521 (3) 1.540 (3) 1.566 (3) 0.96 0.96 0.96 0.96 0.96 0.96 1.494 (3) 0.93. C23—H23B C24—H24A C24—H24B C25—C26 C25—H25A C25—H25B C26—H26A C26—H26B C27—C28 C27—C32 C28—C29 C28—H28 C29—C30 C29—H29 C30—C31 C30—H30 C31—C32 C31—H31 C32—H32. 0.97 0.97 0.97 1.510 (3) 0.97 0.97 0.97 0.97 1.383 (3) 1.383 (3) 1.384 (3) 0.93 1.351 (4) 0.93 1.350 (4) 0.93 1.378 (3) 0.93 0.93. C22—O1—C11 C2—N1—C11 C2—N1—C1 C11—N1—C1 C12—N2—C13 C20—N3—C26 C20—N3—C23 C26—N3—C23 C27—N4—C25 C27—N4—C24 C25—N4—C24 N1—C1—H1A N1—C1—H1B H1A—C1—H1B N1—C1—H1C H1A—C1—H1C H1B—C1—H1C C3—C2—C7 C3—C2—N1 C7—C2—N1 C4—C3—C2 C4—C3—H3 C2—C3—H3 C5—C4—C3 C5—C4—H4 C3—C4—H4 C4—C5—C6. 117.87 (13) 107.83 (14) 119.73 (15) 118.73 (15) 116.58 (16) 116.89 (14) 114.81 (14) 108.20 (15) 116.17 (16) 115.84 (16) 113.25 (16) 109.5 109.5 109.5 109.5 109.5 109.5 121.21 (19) 128.84 (18) 109.95 (16) 117.82 (19) 121.1 121.1 121.6 (2) 119.2 119.2 120.1 (2). C19—C14—C13 C16—C15—C14 C16—C15—H15 C14—C15—H15 C15—C16—C17 C15—C16—H16 C17—C16—H16 C18—C17—C16 C18—C17—H17 C16—C17—H17 C17—C18—C19 C17—C18—H18 C19—C18—H18 C18—C19—C14 C18—C19—C20 C14—C19—C20 C21—C20—N3 C21—C20—C19 N3—C20—C19 C20—C21—C22 C20—C21—H21 C22—C21—H21 C13—C22—O1 C13—C22—C21 O1—C22—C21 N3—C23—C24 N3—C23—H23A. 119.24 (16) 121.07 (19) 119.5 119.5 120.58 (19) 119.7 119.7 120.28 (19) 119.9 119.9 121.08 (19) 119.5 119.5 118.55 (17) 122.52 (17) 118.91 (15) 122.28 (16) 120.05 (16) 117.66 (15) 120.28 (16) 119.9 119.9 121.18 (16) 122.11 (16) 116.70 (15) 109.72 (15) 109.7. Acta Cryst. (2005). E61, o988–o989. sup-5.

(8) supporting information C4—C5—H5 C6—C5—H5 C7—C6—C5 C7—C6—H6 C5—C6—H6 C6—C7—C2 C6—C7—C8 C2—C7—C8 C7—C8—C10 C7—C8—C9 C10—C8—C9 C7—C8—C11 C10—C8—C11 C9—C8—C11 C8—C9—H9A C8—C9—H9B H9A—C9—H9B C8—C9—H9C H9A—C9—H9C H9B—C9—H9C C8—C10—H10A C8—C10—H10B H10A—C10—H10B C8—C10—H10C H10A—C10—H10C H10B—C10—H10C N1—C11—O1 N1—C11—C12 O1—C11—C12 N1—C11—C8 O1—C11—C8 C12—C11—C8 N2—C12—C11 N2—C12—H12 C11—C12—H12 C22—C13—N2 C22—C13—C14 N2—C13—C14 C15—C14—C19 C15—C14—C13. 120.0 120.0 119.09 (19) 120.5 120.5 120.15 (17) 130.93 (17) 108.89 (17) 113.98 (17) 108.58 (16) 109.97 (18) 100.21 (14) 113.44 (16) 110.23 (16) 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 106.18 (13) 112.78 (15) 109.15 (15) 103.73 (14) 109.46 (14) 115.08 (15) 126.17 (17) 116.9 116.9 120.86 (16) 119.38 (16) 119.58 (16) 118.38 (17) 122.37 (17). C24—C23—H23A N3—C23—H23B C24—C23—H23B H23A—C23—H23B N4—C24—C23 N4—C24—H24A C23—C24—H24A N4—C24—H24B C23—C24—H24B H24A—C24—H24B N4—C25—C26 N4—C25—H25A C26—C25—H25A N4—C25—H25B C26—C25—H25B H25A—C25—H25B N3—C26—C25 N3—C26—H26A C25—C26—H26A N3—C26—H26B C25—C26—H26B H26A—C26—H26B C28—C27—C32 C28—C27—N4 C32—C27—N4 C27—C28—C29 C27—C28—H28 C29—C28—H28 C30—C29—C28 C30—C29—H29 C28—C29—H29 C31—C30—C29 C31—C30—H30 C29—C30—H30 C30—C31—C32 C30—C31—H31 C32—C31—H31 C31—C32—C27 C31—C32—H32 C27—C32—H32. 109.7 109.7 109.7 108.2 112.30 (17) 109.1 109.1 109.1 109.1 107.9 112.51 (17) 109.1 109.1 109.1 109.1 107.8 109.82 (15) 109.7 109.7 109.7 109.7 108.2 115.7 (2) 122.03 (19) 122.22 (19) 121.7 (2) 119.2 119.2 121.2 (2) 119.4 119.4 118.2 (2) 120.9 120.9 121.6 (3) 119.2 119.2 121.6 (2) 119.2 119.2. C11—N1—C2—C3 C1—N1—C2—C3 C11—N1—C2—C7 C1—N1—C2—C7 C7—C2—C3—C4 N1—C2—C3—C4 C2—C3—C4—C5. 162.05 (18) 22.1 (3) −18.84 (19) −158.77 (16) −0.3 (3) 178.74 (17) 0.5 (3). C19—C14—C15—C16 C13—C14—C15—C16 C14—C15—C16—C17 C15—C16—C17—C18 C16—C17—C18—C19 C17—C18—C19—C14 C17—C18—C19—C20. 1.1 (3) 179.94 (18) −2.0 (3) 0.6 (3) 1.7 (3) −2.5 (3) 179.02 (19). Acta Cryst. (2005). E61, o988–o989. sup-6.

(9) supporting information C3—C4—C5—C6 C4—C5—C6—C7 C5—C6—C7—C2 C5—C6—C7—C8 C3—C2—C7—C6 N1—C2—C7—C6 C3—C2—C7—C8 N1—C2—C7—C8 C6—C7—C8—C10 C2—C7—C8—C10 C6—C7—C8—C9 C2—C7—C8—C9 C6—C7—C8—C11 C2—C7—C8—C11 C2—N1—C11—O1 C1—N1—C11—O1 C2—N1—C11—C12 C1—N1—C11—C12 C2—N1—C11—C8 C1—N1—C11—C8 C22—O1—C11—N1 C22—O1—C11—C12 C22—O1—C11—C8 C7—C8—C11—N1 C10—C8—C11—N1 C9—C8—C11—N1 C7—C8—C11—O1 C10—C8—C11—O1 C9—C8—C11—O1 C7—C8—C11—C12 C10—C8—C11—C12 C9—C8—C11—C12 C13—N2—C12—C11 N1—C11—C12—N2 O1—C11—C12—N2 C8—C11—C12—N2 C12—N2—C13—C22 C12—N2—C13—C14 C22—C13—C14—C15 N2—C13—C14—C15 C22—C13—C14—C19 N2—C13—C14—C19. Acta Cryst. (2005). E61, o988–o989. −0.4 (3) 0.0 (3) 0.2 (3) −177.37 (19) −0.1 (3) −179.27 (16) 178.00 (16) −1.2 (2) −42.3 (3) 139.90 (18) 80.7 (3) −97.15 (19) −163.80 (19) 18.40 (18) −85.53 (16) 54.9 (2) 154.98 (15) −64.6 (2) 29.81 (17) 170.21 (15) −152.93 (15) −31.1 (2) 95.69 (17) −28.59 (16) −150.48 (16) 85.70 (18) 84.40 (15) −37.5 (2) −161.31 (15) −152.27 (15) 85.8 (2) −38.0 (2) −4.8 (3) 143.92 (19) 26.2 (3) −97.3 (2) −13.2 (3) 171.74 (17) 179.33 (17) −5.5 (3) −1.8 (3) 173.32 (16). C15—C14—C19—C18 C13—C14—C19—C18 C15—C14—C19—C20 C13—C14—C19—C20 C26—N3—C20—C21 C23—N3—C20—C21 C26—N3—C20—C19 C23—N3—C20—C19 C18—C19—C20—C21 C14—C19—C20—C21 C18—C19—C20—N3 C14—C19—C20—N3 N3—C20—C21—C22 C19—C20—C21—C22 N2—C13—C22—O1 C14—C13—C22—O1 N2—C13—C22—C21 C14—C13—C22—C21 C11—O1—C22—C13 C11—O1—C22—C21 C20—C21—C22—C13 C20—C21—C22—O1 C20—N3—C23—C24 C26—N3—C23—C24 C27—N4—C24—C23 C25—N4—C24—C23 N3—C23—C24—N4 C27—N4—C25—C26 C24—N4—C25—C26 C20—N3—C26—C25 C23—N3—C26—C25 N4—C25—C26—N3 C25—N4—C27—C28 C24—N4—C27—C28 C25—N4—C27—C32 C24—N4—C27—C32 C32—C27—C28—C29 N4—C27—C28—C29 C27—C28—C29—C30 C30—C31—C32—C27 C28—C27—C32—C31 N4—C27—C32—C31. 1.1 (3) −177.76 (17) 179.66 (17) 0.8 (3) −25.4 (3) 103.0 (2) 153.37 (17) −78.3 (2) 178.48 (18) 0.0 (3) −0.3 (3) −178.78 (15) 178.97 (16) 0.3 (3) 6.4 (3) −178.50 (16) −172.95 (16) 2.2 (3) 17.7 (2) −162.88 (15) −1.4 (3) 179.26 (16) 163.99 (16) −63.4 (2) 174.65 (17) −47.5 (2) 55.7 (2) −175.04 (17) 47.3 (2) −165.41 (17) 63.1 (2) −55.3 (2) −163.9 (2) −27.3 (3) 16.4 (3) 153.0 (2) 0.6 (4) −179.2 (2) 0.0 (4) 0.5 (4) −0.9 (4) 178.9 (2). sup-7.

(10)

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