3 [(2R*,3S*) 3 (2 Meth­oxy­anilino) 2 methyl 3 phenyl­propionyl]­spiro­[2H 1,3 benzoxazine 2,1′ cyclo­hexan] 4(3H) one

(1)organic papers 3-[(2R*,3S*)-3-(2-Methoxyanilino)-2-methyl3-phenylpropionyl]spiro[2H-1,3-benzoxazine2,10 -cyclohexan]-4(3H)-one. Acta Crystallographica Section E. Structure Reports Online ISSN 1600-5368. Shan-Zhong Jian,a Jian-Ming Gub and Yan-Guang Wanga* a. Department of Chemistry, Zhejiang University, 310027 Hangzhou, People’s Republic of China, and bAnalysis and Measurement Center, Zhejiang University, 310028 Hangzhou, People’s Republic of China. The racemic title compound, C30H32N2O4, was synthesized from spiro[2H-1,3-benzoxazine-2,10 -cyclohexan]-4(3H)-one and N-benzylidene-2-methoxybenzenamine under classical Reformatsky reaction conditions. Intermolecular N—H  O and C—H  O hydrogen bonds link the molecules in the crystal structure into infinite chains along the a axis. These chains form layers parallel to the (001) plane, which are stabilized by weak interlayer C—H  O hydrogen bonds.. Received 22 December 2004 Accepted 8 March 2005 Online 18 March 2005. Correspondence e-mail: orgwyg@zju.edu.cn. Comment Key indicators Single-crystal X-ray study T = 295 K ˚ Mean (C–C) = 0.003 A R factor = 0.031 wR factor = 0.063 Data-to-parameter ratio = 8.0 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.. Fig. 1 shows the structure of (3). Its preparation involved refluxing a mixture of (1) and (2) in the presence of zinc powder (Jian et al., 2005). The mechanism predicts that the product is a racemic mixture of 3-[(2S,3R)- and 3-[(2R,3S)3-(2-methoxyanilino)-2-methyl-3-phenylpropionyl]spiro[2H1,3-benzoxazine-2,10 -cyclohexan]-4(3H)-one. The X-ray crystal structure, reported here, confirms that the mechanism is valid.. The molecular dimensions (Table 1) may be considered normal. Intermolecular N—H  O and C—H  O hydrogen. Figure 1 # 2005 International Union of Crystallography Printed in Great Britain – all rights reserved. o990. Jian, Gu and Wang. . C30H32N2O4. The molecule of compound (3) in the crystal structure. Ellipsoids are drawn at the 30% probability level. doi:10.1107/S1600536805007361. Acta Cryst. (2005). E61, o990–o991.

(2) organic papers Refinement Refinement on F 2 R[F 2 > 2(F 2)] = 0.031 wR(F 2) = 0.063 S = 1.03 2604 reflections 326 parameters H-atom parameters constrained. w = 1/[0.0003Fo2 + (Fo2)]/(4Fo2) (/)max < 0.001 ˚ 3 max = 0.12 e A ˚ 3 min = 0.13 e A Extinction correction: Larson (1970), equation 22 Extinction coefficient: 2.4 (3)  102. Table 1 ˚ ,  ). Selected geometric parameters (A. Figure 2 The molecular packing of (3), viewed approximately along the a axis. Dashed lines indicate the hydrogen-bonding interactions. H atoms not involved in the hydrogen bonding have been omitted (see Table 2 for symmetry codes).. bonds play an important role in the formation of polymeric chains running along the crystallographic b axis (Fig. 2). These chains form layers parallel to the (001) plane. These layers are stabilized by weak interlayer C—H  O hydrogen bonds (Table 2).. O1—C3 O2—C4 O3—C10 O3—C11 O4—C23 O4—C24 N1—C3. 1.213 (2) 1.219 (2) 1.372 (2) 1.443 (2) 1.374 (2) 1.420 (2) 1.430 (2). N1—C11 N2—C17 C1—C2 C1—C3 C1—C17 C4—C5 C5—C10. 1.510 (2) 1.457 (2) 1.530 (2) 1.514 (2) 1.537 (2) 1.465 (3) 1.377 (3). O1—C3—N1 O3—C11—N1. 120.4 (2) 106.2 (1). O3—C11—C12 C3—C1—C2. 103.8 (1) 110.3 (1). Table 2 ˚ ,  ). Hydrogen-bonding geometry (A D—H  A i. N2—H32  O1 C30—H31  O1i C24—H24  O2ii. Experimental A mixture of the carboximide (1) (1.2 mmol), the imine (2) (1 mmol) and zinc dust (2 mmol) in tetrahydrofuran (5 ml) was refluxed for 10– 20 min, cooled and poured into water (5 ml), and then extracted with CH2Cl2 (3  5 ml). The combined extracts were washed with brine, dried over anhydrous Na2SO4, and evaporated in vacuo. The residue was purified by flash column chromatography on silica gel (eluted with hexane/ethyl acetate, 20:1) to give the desired product (402 mg, yield 83%). Colourless crystals were obtained from CH2Cl2/EtOH solution after it was left to stand for 4 d. IR (KBr): 3380, 1718, 1678 cm1. 1H NMR (500 MHz, CDCl3):  1.08 (d, J = 7.9 Hz), 1.40– 2.30 (m, 10H), 3.61 (qd, 1H, J = 7.9 Hz, J = 9.9 Hz), 3.83 (s, 3H), 4.60 (d, 1H, J = 9.9 Hz), 6.47–8.05 (m, 13H). 13C NMR (125 MHz, CDCl3):  16.79, 22.56, 22.65, 24.55, 32.79, 33.10, 51.08, 55.96, 61.97, 95.88, 110.02, 111.18, 116.34, 117.43, 117.74, 121.42, 122.48, 127.57, 127.77, 128.60, 136.15, 137.22, 141.82, 147.03, 155.68, 164.02, 183.26. ESI–MS: m/z 485 ([M + 1] +); HRMS (ESI) m/z found for [M + H]+ 485.2438, calculated for C30H33N2O4+ 485.2435. Crystal data C30H32N2O4 Mr = 484.59 Orthorhombic, Pbcn ˚ a = 24.1025 (4) A ˚ b = 11.0675 (5) A ˚ c = 19.0716 (2) A ˚3 V = 5087.4 (3) A Z=8 Dx = 1.265 Mg m3. Mo K radiation Cell parameters from 42 864 reflections  = 1.4–27.5  = 0.08 mm1 T = 295 (1) K Block, colourless 0.16  0.10  0.08 mm. Data collection Rigaku R-AXIS RAPID diffractometer ! scans Absorption correction: none 43 304 measured reflections 5694 independent reflections Acta Cryst. (2005). E61, o990–o991. 2604 reflections with F 2 > 2(F 2) Rint = 0.061 max = 27.5 h = 31 ! 31 k = 14 ! 12 l = 24 ! 24. D—H. H  A. D  A. D—H  A. 0.90 0.98 0.96. 2.44 2.48 2.69. 3.329 (2) 3.307 (3) 3.544 (2). 168 142 148. Symmetry codes: (i) 12  x; 12 þ y; z; (ii) 12  x; 32  y; z  12.. Atom H32 was found in a difference Fourier map and fixed in position. The other H atoms were placed in calculated positions, with ˚ , and included in the final cycles of refinement C—H = 0.96 or 0.97 A in the riding-model approximation, with Uiso(H) = 1.2Ueq of the carrier atoms. Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO ; data reduction: CrystalStructure (Rigaku/ MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.. The authors thank the National Natural Science Foundation of China (grant No. 20272051), as well as the Teaching and Research Award Programme for Outstanding Young Teachers in Higher Education Institutions of MOE, China.. References Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, C. K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Jian, S.-Z., Ma, C. & Wang, Y. G. (2005). Synthesis. In the press. Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall and C. P. Huber, pp. 291–294. Copenhagen: Munksgaard. Rigaku (1998). PROCESS-AUTO. Version 1.06. Rigaku Corporation, Tokyo, Japan. Rigaku/MSC (2004). CrystalStructure. Version 3.6.0. Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA. Sheldrick, G. M. (1997). SHELXS97. University of Go¨ttingen, Germany. Jian, Gu and Wang. . C30H32N2O4. o991.

(3) supporting information. supporting information Acta Cryst. (2005). E61, o990–o991. [https://doi.org/10.1107/S1600536805007361]. 3-[(2R*,3S*)-3-(2-Methoxyanilino)-2-methyl-3-phenylpropionyl]spiro[2H-1,3benzoxazine-2,1′-cyclohexan]-4(3H)-one Shan-Zhong Jian, Jian-Ming Gu and Yan-Guang Wang (3) Crystal data C30H32N2O4 Mr = 484.59 Orthorhombic, Pbcn Hall symbol: -P 2n 2ab a = 24.1025 (4) Å b = 11.0675 (5) Å c = 19.0716 (2) Å V = 5087.4 (3) Å3 Z=8. F(000) = 2064.00 Dx = 1.265 Mg m−3 Mo Kα radiation, λ = 0.7107 Å Cell parameters from 42864 reflections θ = 1.4–27.5° µ = 0.08 mm−1 T = 295 K Platelet, colorless 0.16 × 0.10 × 0.08 mm. Data collection 2604 reflections with F2 > 2σ(F2) Rint = 0.061 θmax = 27.5° h = −31→31 k = −14→12 l = −24→24. Rigaku R-AXIS RAPID diffractometer Detector resolution: 10.00 pixels mm-1 ω scans 43304 measured reflections 5694 independent reflections Refinement Refinement on F2 R[F2 > 2σ(F2)] = 0.031 wR(F2) = 0.063 S = 1.03 2604 reflections 326 parameters H-atom parameters constrained. w = 1/[0.0003Fo2 + σ(Fo2)]/(4Fo2) (Δ/σ)max < 0.001 Δρmax = 0.12 e Å−3 Δρmin = −0.13 e Å−3 Extinction correction: Larson (1970), equation 22 Extinction coefficient: 240 (30). Special details Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2). O1. x. y. z. Uiso*/Ueq. 0.27996 (5). 0.4327 (1). 0.52383 (7). 0.0506 (4). Acta Cryst. (2005). E61, o990–o991. sup-1.

(4) supporting information O2 O3 O4 N1 N2 C1 C2 C3 C4 C5 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 H1 H2 H3 H4 H5 H6 H7 H8 H9 H10 H11 H12 H13. 0.34131 (6) 0.39588 (5) 0.21313 (6) 0.33472 (6) 0.19778 (6) 0.23960 (7) 0.23057 (8) 0.28531 (8) 0.36077 (9) 0.41308 (8) 0.44631 (9) 0.4946 (1) 0.5096 (1) 0.47716 (9) 0.42913 (9) 0.36787 (8) 0.33090 (8) 0.36601 (9) 0.4087 (1) 0.44490 (9) 0.40958 (8) 0.18638 (7) 0.17226 (7) 0.14137 (8) 0.11824 (9) 0.12547 (9) 0.15698 (9) 0.18059 (8) 0.2372 (1) 0.13857 (9) 0.09107 (9) 0.0474 (1) 0.0507 (1) 0.0977 (1) 0.1416 (1) 0.2494 0.2022 0.2190 0.2645 0.4353 0.5181 0.5440 0.4879 0.3069 0.3085 0.3417 0.3853 0.3894. Acta Cryst. (2005). E61, o990–o991. 0.6213 (1) 0.7081 (1) 0.7781 (1) 0.5973 (1) 0.6412 (1) 0.5750 (2) 0.4904 (2) 0.5270 (2) 0.6394 (2) 0.7045 (2) 0.7365 (2) 0.8001 (2) 0.8327 (2) 0.8022 (2) 0.7370 (2) 0.5932 (2) 0.5902 (2) 0.5913 (2) 0.4899 (2) 0.4938 (2) 0.4905 (2) 0.5814 (2) 0.6061 (2) 0.5010 (2) 0.4704 (2) 0.5441 (2) 0.6488 (2) 0.6782 (2) 0.8353 (2) 0.6371 (2) 0.5725 (2) 0.6241 (3) 0.7410 (3) 0.8069 (2) 0.7551 (2) 0.6558 0.5233 0.4128 0.4826 0.7137 0.8224 0.8782 0.8261 0.6604 0.5174 0.5818 0.6681 0.4130. 0.66668 (7) 0.47564 (6) 0.38113 (6) 0.54790 (7) 0.49153 (7) 0.60232 (8) 0.66468 (9) 0.55551 (9) 0.6087 (1) 0.5983 (1) 0.6547 (1) 0.6440 (1) 0.5766 (1) 0.5199 (1) 0.5316 (1) 0.48079 (9) 0.41643 (9) 0.34962 (9) 0.3493 (1) 0.4145 (1) 0.4807 (1) 0.55805 (9) 0.42943 (9) 0.4213 (1) 0.3570 (1) 0.3001 (1) 0.3064 (1) 0.36964 (9) 0.3218 (1) 0.59816 (9) 0.6124 (1) 0.6487 (1) 0.6704 (1) 0.6579 (1) 0.6219 (1) 0.6193 0.6943 0.6475 0.6906 0.7024 0.6839 0.5690 0.4724 0.4167 0.4174 0.3094 0.3464 0.3477. 0.0662 (5) 0.0464 (4) 0.0518 (4) 0.0401 (5) 0.0402 (5) 0.0395 (6) 0.0558 (7) 0.0397 (6) 0.0456 (6) 0.0429 (6) 0.0549 (7) 0.0641 (8) 0.0688 (8) 0.0611 (7) 0.0455 (6) 0.0398 (6) 0.0491 (6) 0.0579 (7) 0.0644 (8) 0.0585 (7) 0.0473 (6) 0.0386 (6) 0.0367 (5) 0.0470 (6) 0.0549 (7) 0.0586 (7) 0.0517 (7) 0.0404 (6) 0.0641 (8) 0.0420 (6) 0.0552 (7) 0.0738 (9) 0.080 (1) 0.083 (1) 0.0653 (8) 0.047* 0.067* 0.067* 0.067* 0.066* 0.077* 0.082* 0.073* 0.059* 0.059* 0.069* 0.069* 0.077*. sup-2.

(5) supporting information H14 H15 H16 H17 H18 H19 H20 H21 H22 H23 H24 H25 H26 H27 H28 H29 H30 H31 H32. 0.4320 0.4696 0.4667 0.3899 0.4335 0.1758 0.1357 0.0969 0.1083 0.1623 0.2080 0.2585 0.2607 0.0882 0.0139 0.0194 0.1003 0.1752 0.2078. 0.4979 0.4245 0.5675 0.4142 0.4981 0.4980 0.4477 0.3955 0.5234 0.7015 0.8678 0.7774 0.8997 0.4885 0.5769 0.7781 0.8909 0.8025 0.7193. 0.3081 0.4144 0.4140 0.4829 0.5214 0.5472 0.4617 0.3523 0.2551 0.2656 0.2932 0.2956 0.3377 0.5966 0.6588 0.6954 0.6740 0.6131 0.4953. 0.077* 0.070* 0.070* 0.057* 0.057* 0.046* 0.056* 0.066* 0.070* 0.062* 0.077* 0.077* 0.077* 0.066* 0.089* 0.096* 0.099* 0.078* 0.048*. Atomic displacement parameters (Å2). O1 O2 O3 O4 N1 N2 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19. U11. U22. U33. U12. U13. U23. 0.0509 (9) 0.051 (1) 0.0473 (9) 0.066 (1) 0.032 (1) 0.044 (1) 0.035 (1) 0.048 (1) 0.037 (1) 0.039 (1) 0.033 (1) 0.043 (1) 0.043 (2) 0.044 (2) 0.053 (2) 0.038 (1) 0.036 (1) 0.045 (1) 0.061 (2) 0.065 (2) 0.048 (1) 0.042 (1) 0.035 (1) 0.029 (1) 0.041 (1). 0.0468 (8) 0.109 (1) 0.0453 (8) 0.0517 (9) 0.053 (1) 0.0429 (9) 0.047 (1) 0.076 (1) 0.047 (1) 0.058 (1) 0.049 (1) 0.066 (1) 0.072 (2) 0.067 (2) 0.060 (1) 0.043 (1) 0.044 (1) 0.061 (1) 0.074 (1) 0.075 (2) 0.062 (1) 0.049 (1) 0.044 (1) 0.042 (1) 0.051 (1). 0.0542 (8) 0.0379 (8) 0.0467 (8) 0.0379 (7) 0.0362 (9) 0.0340 (8) 0.036 (1) 0.043 (1) 0.035 (1) 0.040 (1) 0.047 (1) 0.055 (1) 0.077 (2) 0.096 (2) 0.070 (2) 0.055 (1) 0.039 (1) 0.041 (1) 0.039 (1) 0.053 (1) 0.065 (1) 0.050 (1) 0.037 (1) 0.038 (1) 0.049 (1). −0.0017 (8) −0.0198 (9) −0.0034 (7) −0.0089 (8) −0.0028 (9) −0.0080 (8) −0.004 (1) −0.002 (1) 0.000 (1) 0.003 (1) −0.001 (1) 0.000 (1) −0.006 (1) −0.016 (1) −0.013 (1) 0.000 (1) −0.001 (1) 0.002 (1) −0.005 (1) −0.002 (1) 0.009 (1) 0.003 (1) −0.005 (1) 0.006 (1) −0.001 (1). 0.0023 (7) 0.0023 (7) 0.0030 (7) 0.0025 (7) 0.0025 (7) 0.0004 (8) 0.0031 (9) 0.001 (1) −0.003 (1) 0.000 (1) 0.002 (1) −0.004 (1) −0.008 (1) 0.006 (2) 0.012 (1) 0.001 (1) 0.0049 (9) −0.001 (1) 0.005 (1) 0.018 (1) 0.013 (1) 0.001 (1) 0.0018 (9) −0.0012 (9) −0.000 (1). −0.0059 (7) −0.0050 (8) 0.0016 (6) 0.0065 (7) −0.0031 (7) 0.0018 (7) −0.0004 (9) 0.012 (1) 0.005 (1) −0.005 (1) −0.007 (1) −0.012 (1) −0.018 (1) −0.014 (1) −0.006 (1) −0.007 (1) −0.0008 (9) −0.000 (1) −0.003 (1) −0.014 (1) −0.009 (1) −0.003 (1) 0.0034 (9) −0.0050 (9) −0.003 (1). Acta Cryst. (2005). E61, o990–o991. sup-3.

(6) supporting information C20 C21 C22 C23 C24 C25 C26 C27 C28 C29 C30. 0.043 (1) 0.047 (2) 0.050 (1) 0.040 (1) 0.067 (2) 0.038 (1) 0.038 (1) 0.041 (2) 0.070 (2) 0.103 (2) 0.067 (2). 0.061 (1) 0.082 (2) 0.068 (1) 0.044 (1) 0.072 (2) 0.052 (1) 0.073 (2) 0.112 (2) 0.113 (2) 0.071 (2) 0.057 (1). 0.061 (1) 0.046 (1) 0.037 (1) 0.037 (1) 0.054 (1) 0.036 (1) 0.054 (1) 0.068 (2) 0.057 (2) 0.075 (2) 0.072 (1). −0.002 (1) 0.008 (1) 0.008 (1) 0.007 (1) −0.005 (1) 0.002 (1) −0.004 (1) 0.005 (2) 0.035 (2) 0.021 (2) −0.000 (1). −0.002 (1) −0.006 (1) −0.001 (1) 0.002 (1) 0.009 (1) 0.001 (1) 0.002 (1) 0.013 (1) 0.025 (1) 0.030 (2) 0.026 (1). −0.017 (1) −0.022 (1) −0.004 (1) −0.0025 (9) 0.013 (1) 0.0070 (9) 0.004 (1) 0.014 (2) 0.013 (2) 0.001 (1) 0.001 (1). Geometric parameters (Å, º) O1—C3 O2—C4 O3—C10 O3—C11 O4—C23 O4—C24 N1—C3 N1—C4 N1—C11 N2—C17 N2—C18 C1—C2 C1—C3 C1—C17 C4—C5 C5—C6 C5—C10 C6—C7 C7—C8 C8—C9 C9—C10 C11—C12 C11—C16 C12—C13 C13—C14 C14—C15 C15—C16 C17—C25 C18—C19 C18—C23 C19—C20 C20—C21 C21—C22 C22—C23. Acta Cryst. (2005). E61, o990–o991. 1.213 (2) 1.219 (2) 1.372 (2) 1.443 (2) 1.374 (2) 1.420 (2) 1.430 (2) 1.398 (2) 1.510 (2) 1.457 (2) 1.390 (2) 1.530 (2) 1.514 (2) 1.537 (2) 1.465 (3) 1.388 (3) 1.377 (3) 1.376 (3) 1.383 (4) 1.376 (3) 1.382 (3) 1.517 (3) 1.517 (3) 1.530 (3) 1.522 (3) 1.520 (3) 1.524 (3) 1.514 (3) 1.390 (3) 1.406 (2) 1.389 (3) 1.369 (3) 1.390 (3) 1.374 (3). C26—C27 C27—C28 C28—C29 C29—C30 N2—H32 C1—H1 C2—H2 C2—H3 C2—H4 C6—H5 C7—H6 C8—H7 C9—H8 C12—H9 C12—H10 C13—H11 C13—H12 C14—H13 C14—H14 C15—H15 C15—H16 C16—H17 C16—H18 C17—H19 C19—H20 C20—H21 C21—H22 C22—H23 C24—H24 C24—H25 C24—H26 C26—H27 C27—H28 C28—H29. 1.385 (3) 1.361 (4) 1.369 (4) 1.386 (4) 0.9013 0.9800 0.9600 0.9600 0.9600 0.9800 0.9800 0.9800 0.9800 0.9700 0.9700 0.9700 0.9700 0.9700 0.9700 0.9700 0.9700 0.9700 0.9700 0.9800 0.9800 0.9800 0.9800 0.9800 0.9600 0.9600 0.9600 0.9800 0.9800 0.9800. sup-4.

(7) supporting information C25—C26 C25—C30. 1.377 (3) 1.385 (3). C29—H30 C30—H31. 0.9800 0.9800. O1—C3—N1 O1—C3—C1 O2—C4—N1 O2—C4—C5 C11—O3—C10 O3—C10—C5 O3—C10—C9 O3—C11—N1 O3—C11—C12 O3—C11—C16 O4—C23—C18 O4—C23—C22 C24—O4—C23 N1—C3—C1 C4—N1—C3 C11—N1—C3 C11—N1—C4 N1—C4—C5 N1—C11—C12 N1—C11—C16 N2—C17—C1 C18—N2—C17 N2—C17—C25 N2—C18—C23 N2—C18—C19 C3—C1—C2 C17—C1—C2 C17—C1—C3 C1—C17—C25 C4—C5—C6 C4—C5—C10 C10—C5—C6 C5—C6—C7 C5—C10—C9 C6—C7—C8 C7—C8—C9 C8—C9—C10 C16—C11—C12 C11—C12—C13 C11—C16—C15 C12—C13—C14 C13—C14—C15 C14—C15—C16 C17—C25—C26 C17—C25—C30. 120.4 (2) 121.2 (2) 121.7 (2) 122.3 (2) 115.2 (1) 119.5 (2) 119.1 (2) 106.2 (1) 103.8 (1) 110.5 (1) 114.1 (1) 124.6 (2) 117.7 (1) 118.3 (2) 118.1 (1) 120.7 (1) 118.4 (1) 116.0 (2) 112.1 (1) 112.0 (1) 110.0 (1) 122.1 (1) 113.5 (1) 118.0 (2) 124.4 (2) 110.3 (1) 109.7 (1) 107.4 (1) 112.1 (1) 121.1 (2) 119.7 (2) 119.2 (2) 120.2 (2) 121.3 (2) 119.6 (2) 121.1 (2) 118.6 (2) 111.8 (2) 110.4 (2) 110.7 (2) 111.8 (2) 111.3 (2) 110.9 (2) 121.4 (2) 120.6 (2). C1—C2—H3 C1—C2—H4 C1—C2—H2 H1—C1—C3 H1—C1—C17 C1—C17—H19 H3—C2—H2 H4—C2—H2 H4—C2—H3 C5—C6—H5 H5—C6—C7 C6—C7—H6 H6—C7—C8 C7—C8—H7 C8—C9—H8 H7—C8—C9 H8—C9—C10 C11—C12—H9 C11—C12—H10 C11—C16—H17 C11—C16—H18 H9—C12—C13 H10—C12—C13 C12—C13—H12 C12—C13—H11 H10—C12—H9 H12—C13—C14 H11—C13—C14 C13—C14—H13 C13—C14—H14 H12—C13—H11 C14—C15—H16 H13—C14—C15 C14—C15—H15 H14—C14—C15 H14—C14—H13 C15—C16—H17 H16—C15—C16 C15—C16—H18 H15—C15—C16 H16—C15—H15 H18—C16—H17 H19—C17—C25 C18—C19—H20 H20—C19—C20. 108.8921 109.4943 109.0277 109.8859 109.9184 106.8730 109.4662 109.8103 110.1273 119.7758 120.0105 120.1564 120.2846 119.4727 120.7202 119.3863 120.7192 109.2003 109.2654 109.1183 109.1683 109.1756 109.3070 109.0038 108.8865 109.4619 108.7971 108.8719 108.9042 109.1931 109.4707 109.0600 108.9645 109.2130 108.9805 109.4647 109.2652 109.2597 109.1555 108.9308 109.4599 109.4600 106.9568 119.3255 119.5263. Acta Cryst. (2005). E61, o990–o991. sup-5.

(8) supporting information C23—C18—C19 C18—C19—C20 C18—C23—C22 C19—C20—C21 C20—C21—C22 C21—C22—C23 C30—C25—C26 C25—C26—C27 C25—C30—C29 C26—C27—C28 C27—C28—C29 C28—C29—C30 O4—C24—H24 O4—C24—H25 O4—C24—H26 N2—C17—H19 H32—N2—C17 H32—N2—C18 H1—C1—C2. 117.5 (2) 121.1 (2) 121.3 (2) 120.2 (2) 119.9 (2) 119.9 (2) 118.0 (2) 121.1 (2) 120.8 (2) 120.0 (2) 120.1 (3) 119.9 (2) 108.6993 109.5754 108.6413 107.0319 114.6157 117.0572 109.6349. C19—C20—H21 H21—C20—C21 C20—C21—H22 C21—C22—H23 H22—C21—C22 H23—C22—C23 H25—C24—H24 H26—C24—H24 H26—C24—H25 C25—C26—H27 C25—C30—H31 H27—C26—C27 C26—C27—H28 H28—C27—C28 C27—C28—H29 C28—C29—H30 H29—C28—C29 C29—C30—H31 H30—C29—C30. 119.8475 119.9124 120.0829 120.0296 120.0205 120.0389 110.2100 109.4649 110.2145 119.4555 119.5364 119.4173 120.2497 119.7180 120.0867 120.2401 119.7730 119.6828 119.8634. Hydrogen-bond geometry (Å, º) D—H···A i. N2—H32···O1 C30—H31···O1i C24—H24···O2ii. D—H. H···A. D···A. D—H···A. 0.90 0.98 0.96. 2.44 2.48 2.69. 3.329 (2) 3.307 (3) 3.544 (2). 168 142 148. Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) −x+1/2, −y+3/2, z−1/2.. Acta Cryst. (2005). E61, o990–o991. sup-6.

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