In the title compound, C30H36N2O2S, the dihedral angle between the two aromatic rings of the biphenyl residue is 31.2 (1)°. The two methyl­ene C atoms subtend an angle of 99.9 (1)° at the S atom. In the crystal, mol­ecules form inversion dimers linked by pairs of N—H⋯O hydrogen bonds. The hydroxyl group is shielded by the tert-butyl residues and is therefore not involved in any hydrogen bonding

Azhar Ariffin

Barbour

Noorsaadah Abdul Rahman

Seik Weng Ng

Sheldrick

Wagee A. Yehye

Yehye

Acta Crystallographica Section E

English

PubMed

In the title compound, C30H36N2O2S, the dihedral angle between the two aromatic rings of the biphenyl residue is 31.2&amp;#8197;(1)&amp;#176;. The two methylene C atoms subtend an angle of 99.9&amp;#8197;(1)&amp;#176; at the S atom. In the crystal, molecules form inversion dimers linked by pairs of N&amp;#8212;H...O hydrogen bonds. The hydroxyl group is shielded by the tert-butyl residues and is therefore not involved in any hydrogen bonding

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Acta Crystallographica Section E Structure Reports Online

N&amp;#8242;-[(Biphenyl-4-yl)methylene]-2-[(3,5-di-tert-butyl-4-hydroxybenzyl)sulfanyl]acetohydrazide

In the title compound, C(30)H(36)N(2)O(2)S, the dihedral angle between the two aromatic rings of the biphenyl residue is 31.2 (1)degrees. The two methylene C atoms subtend an angle of 99.9 (1)degrees at the S atom. In the crystal, molecules form inversion dimers linked by pairs of N-H center dot center dot center dot O hydrogen bonds. The hydroxyl group is shielded by the tert-butyl residues and is therefore not involved in any hydrogen bonding

Ariffin, Azhar

Ng, S.W.

Yehye, W.A.

Rahman, N.A.

UM Digital Repository

N0-[(Biphenyl-4-yl)methylene]-2-[(3,5-di-tert-butyl-4-hydroxybenzyl)sulfanyl]-acetohydrazideWagee A. Yehye, Azhar Ariffin, Noorsaadah AbdulRahman and Seik Weng Ng*Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, MalaysiaCorrespondence e-mail: seikweng@um.edu.myReceived 23 February 2010; accepted 23 February 2010Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.004 A˚;R factor = 0.047; wR factor = 0.135; data-to-parameter ratio = 15.0.In the title compound, C30H36N2O2S, the dihedral anglebetween the two aromatic rings of the biphenyl residue is31.2 (1). The two methylene C atoms subtend an angle of99.9 (1) at the S atom. In the crystal, molecules forminversion dimers linked by pairs of N—H  O hydrogenbonds. The hydroxyl group is shielded by the tert-butylresidues and is therefore not involved in any hydrogenbonding.Related literatureWhen heated in acidified ethanol the compound gavebiphenyl-4-carbaldehyde azine; see: Yehye et al. (2008).ExperimentalCrystal dataC30H36N2O2S Mr = 488.67Triclinic, P1a = 9.1104 (11) A˚b = 10.5601 (12) A˚c = 15.5146 (18) A˚ = 104.435 (2) = 102.805 (2) = 97.559 (2)V = 1381.7 (3) A˚3Z = 2Mo K radiation = 0.15 mm1T = 293 K0.40  0.10  0.10 mmData collectionBruker SMART APEXdiffractometerAbsorption correction: multi-scan(SADABS; Sheldrick, 1996)Tmin = 0.944, Tmax = 0.98610977 measured reflections4873 independent reflections3404 reflections with I > 2(I)Rint = 0.035RefinementR[F 2 > 2(F 2)] = 0.047wR(F 2) = 0.135S = 1.044873 reflections324 parameters2 restraintsH atoms treated by a mixture ofindependent and constrainedrefinementmax = 0.17 e A˚3min = 0.19 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AN1—H1  O2i 0.87 (1) 1.97 (1) 2.827 (2) 174 (2)Symmetry code: (i) x þ 1;yþ 1;zþ 1.Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT(Bruker, 2009); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material forpublication: publCIF (Westrip, 2010).We thank the University of Malaya (grant No. FS338/2008 A) for supporting this study.Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: BT5202).ReferencesBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.Sheldrick, G. M. (1996). SADABS. University of Go¨ttingen, Germany.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Westrip, S. P. (2010). publCIF. In preparation.Yehye, W. A., Ariffin, A., Rahman, N. A. & Ng, S. W. (2008). Acta Cryst. E64,o2444.organic compoundso734 Yehye et al. doi:10.1107/S1600536810006884 Acta Cryst. (2010). E66, o734Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supplementary materialssupplementary materialssup-1Acta Cryst. (2010). E66, o734    [ doi:10.1107/S1600536810006884 ]N'-[(Biphenyl-4-yl)methylene]-2-[(3,5-di-tert-butyl-4-hydroxybenzyl)sulfanyl]acetohydrazideW. A. Yehye, A. Ariffin, N. A. Rahman and S. W. NgExperimental2-(3,5-Di-tert-butyl-4-hydroxybenzylthio)acetohydrazine (0.5 g, 1.54 mmol) and 4-phenylbenzaldehyde (0.28 g, 1.54mmol) were stirred in ethanol (10 ml) for 2 h. The resulting solid was collected and recrystallized from ethanol to give theSchiff base as large prismatic crystals in 90% yield. The formulation was assumed from 1H NMR spectral analysis.RefinementCarbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.98 Å) and were included in the refinementin the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The hydroxy and amino H-atoms were located in adifference Fourier map, and were refined isotropically with distance restraints of O–H 0.84±0.01 Å and N–H 0.86±0.01 Å.FiguresFig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C30H36N2O2S at the the50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.N'-[(Biphenyl-4-yl)methylene]-2-[(3,5-di-tert-butyl-4- hydroxybenzyl)sulfanyl]acetohydrazideCrystal dataC30H36N2O2S Z = 2Mr = 488.67 F(000) = 524Triclinic, P1 Dx = 1.175 Mg m−3Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Åa = 9.1104 (11) Å Cell parameters from 2001 reflectionsb = 10.5601 (12) Å θ = 2.3–21.2°c = 15.5146 (18) Å µ = 0.15 mm−1α = 104.435 (2)° T = 293 Kβ = 102.805 (2)° Prism, colorlessγ = 97.559 (2)° 0.40 × 0.10 × 0.10 mmV = 1381.7 (3) Å3Data collectionBruker SMART APEXdiffractometer 4873 independent reflectionssupplementary materialssup-2Radiation source: fine-focus sealed tube 3404 reflections with I > 2σ(I)graphite Rint = 0.035ω scans θmax = 25.0°, θmin = 2.0°Absorption correction: multi-scan(SADABS; Sheldrick, 1996) h = −10→10Tmin = 0.944, Tmax = 0.986 k = −12→1210977 measured reflections l = −16→18RefinementRefinement on F2Primary atom site location: structure-invariant directmethodsLeast-squares matrix: full Secondary atom site location: difference Fourier mapR[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouringsiteswR(F2) = 0.135H atoms treated by a mixture of independent andconstrained refinementS = 1.04w = 1/[σ2(Fo2) + (0.0664P)2 + 0.0264P]where P = (Fo2 + 2Fc2)/34873 reflections (Δ/σ)max = 0.001324 parameters Δρmax = 0.17 e Å−32 restraints Δρmin = −0.19 e Å−3Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)x y z Uiso*/UeqS1 0.76556 (7) 0.68306 (6) 0.78801 (4) 0.0490 (2)O1 0.5035 (2) 0.7947 (2) 1.15128 (12) 0.0773 (6)H1O 0.414 (2) 0.758 (5) 1.146 (4) 0.20 (2)*O2 0.54723 (17) 0.65943 (15) 0.58105 (10) 0.0543 (4)N1 0.7059 (2) 0.51789 (18) 0.55439 (12) 0.0445 (5)H1 0.6318 (18) 0.4645 (17) 0.5098 (11) 0.048 (6)*N2 0.8470 (2) 0.48554 (18) 0.57906 (12) 0.0449 (4)C1 0.5274 (2) 0.7853 (2) 1.06541 (15) 0.0472 (6)C2 0.4146 (2) 0.7092 (2) 0.98530 (15) 0.0443 (5)C3 0.4476 (2) 0.7061 (2) 0.90205 (15) 0.0475 (6)H3 0.3756 0.6556 0.8477 0.057*C4 0.5832 (2) 0.7749 (2) 0.89644 (15) 0.0465 (6)C5 0.6914 (2) 0.8472 (2) 0.97723 (15) 0.0468 (6)H5 0.7831 0.8931 0.9736 0.056*C6 0.6687 (2) 0.8541 (2) 1.06363 (15) 0.0428 (5)C7 0.2608 (2) 0.6336 (2) 0.98892 (17) 0.0538 (6)C8 0.2880 (3) 0.5279 (3) 1.0406 (2) 0.0774 (8)H8A 0.3423 0.4667 1.0100 0.116*H8B 0.1910 0.4801 1.0409 0.116*H8C 0.3477 0.5711 1.1029 0.116*C9 0.1710 (3) 0.7315 (3) 1.0355 (2) 0.0724 (8)H9A 0.0774 0.6826 1.0394 0.109*supplementary materialssup-3H9B 0.1475 0.7919 0.9997 0.109*H9C 0.2323 0.7811 1.0964 0.109*C10 0.1580 (3) 0.5607 (3) 0.8920 (2) 0.0779 (8)H10A 0.2075 0.4953 0.8612 0.117*H10B 0.1405 0.6238 0.8575 0.117*H10C 0.0616 0.5174 0.8963 0.117*C11 0.7924 (3) 0.9341 (2) 1.15209 (15) 0.0513 (6)C12 0.7331 (3) 1.0494 (3) 1.20689 (19) 0.0837 (9)H12A 0.6451 1.0141 1.2243 0.126*H12B 0.7047 1.1066 1.1693 0.126*H12C 0.8124 1.0995 1.2613 0.126*C13 0.8421 (3) 0.8430 (3) 1.21158 (19) 0.0748 (8)H13A 0.7556 0.8054 1.2292 0.112*H13B 0.9211 0.8940 1.2659 0.112*H13C 0.8808 0.7725 1.1768 0.112*C14 0.9374 (3) 0.9949 (3) 1.13007 (19) 0.0720 (8)H14A 1.0121 1.0454 1.1865 0.108*H14B 0.9115 1.0525 1.0924 0.108*H14C 0.9793 0.9248 1.0976 0.108*C15 0.6138 (3) 0.7729 (3) 0.80454 (16) 0.0578 (6)H15A 0.6433 0.8635 0.8025 0.069*H15B 0.5212 0.7302 0.7553 0.069*C16 0.7967 (2) 0.7190 (2) 0.68495 (14) 0.0445 (5)H16A 0.7939 0.8118 0.6893 0.053*H16B 0.8969 0.7036 0.6786 0.053*C17 0.6743 (2) 0.6309 (2) 0.60228 (14) 0.0415 (5)C18 0.8649 (3) 0.3747 (2) 0.53133 (15) 0.0486 (6)H18 0.7843 0.3207 0.4826 0.058*C19 1.0115 (2) 0.3318 (2) 0.55261 (15) 0.0448 (5)C20 1.0305 (3) 0.2105 (2) 0.50071 (16) 0.0520 (6)H20 0.9502 0.1578 0.4513 0.062*C21 1.1672 (3) 0.1671 (2) 0.52141 (16) 0.0508 (6)H21 1.1770 0.0852 0.4857 0.061*C22 1.2902 (2) 0.2427 (2) 0.59426 (15) 0.0438 (5)C23 1.2704 (3) 0.3650 (2) 0.64509 (16) 0.0539 (6)H23 1.3511 0.4186 0.6939 0.065*C24 1.1346 (3) 0.4084 (2) 0.62486 (16) 0.0549 (6)H24 1.1251 0.4906 0.6602 0.066*C25 1.4349 (3) 0.1944 (2) 0.61918 (15) 0.0470 (6)C26 1.4334 (3) 0.0584 (3) 0.60401 (17) 0.0578 (6)H26 1.3410 −0.0024 0.5761 0.069*C27 1.5670 (3) 0.0121 (3) 0.62980 (19) 0.0703 (8)H27 1.5640 −0.0788 0.6199 0.084*C28 1.7033 (3) 0.1010 (4) 0.6700 (2) 0.0748 (8)H28 1.7932 0.0703 0.6875 0.090*C29 1.7081 (3) 0.2344 (3) 0.68445 (19) 0.0719 (8)H29 1.8015 0.2940 0.7112 0.086*C30 1.5748 (3) 0.2822 (3) 0.65969 (18) 0.0607 (7)H30 1.5794 0.3734 0.6703 0.073*supplementary materialssup-4Atomic displacement parameters (Å2)U11 U22 U33 U12 U13 U23S1 0.0509 (4) 0.0565 (4) 0.0402 (3) 0.0122 (3) 0.0105 (3) 0.0156 (3)O1 0.0721 (13) 0.1141 (16) 0.0468 (11) −0.0004 (12) 0.0283 (10) 0.0237 (10)O2 0.0481 (9) 0.0556 (10) 0.0505 (10) 0.0197 (8) 0.0053 (7) 0.0020 (7)N1 0.0409 (11) 0.0479 (11) 0.0375 (11) 0.0131 (9) 0.0044 (9) 0.0024 (9)N2 0.0435 (11) 0.0508 (11) 0.0427 (11) 0.0165 (9) 0.0120 (8) 0.0135 (9)C1 0.0484 (13) 0.0578 (14) 0.0400 (13) 0.0093 (11) 0.0186 (11) 0.0169 (11)C2 0.0395 (12) 0.0499 (13) 0.0463 (13) 0.0104 (10) 0.0133 (10) 0.0166 (11)C3 0.0421 (12) 0.0549 (14) 0.0426 (13) 0.0100 (10) 0.0075 (10) 0.0119 (11)C4 0.0441 (13) 0.0619 (15) 0.0389 (13) 0.0151 (11) 0.0156 (10) 0.0177 (11)C5 0.0415 (12) 0.0554 (14) 0.0473 (14) 0.0050 (10) 0.0160 (11) 0.0203 (11)C6 0.0415 (12) 0.0453 (13) 0.0432 (13) 0.0070 (10) 0.0119 (10) 0.0158 (10)C7 0.0394 (12) 0.0612 (15) 0.0635 (16) 0.0065 (11) 0.0167 (11) 0.0220 (13)C8 0.0623 (17) 0.0742 (19) 0.111 (2) 0.0098 (14) 0.0326 (17) 0.0471 (18)C9 0.0513 (15) 0.086 (2) 0.090 (2) 0.0194 (14) 0.0322 (15) 0.0283 (16)C10 0.0483 (16) 0.086 (2) 0.084 (2) −0.0105 (14) 0.0134 (14) 0.0132 (16)C11 0.0503 (13) 0.0509 (14) 0.0456 (13) 0.0032 (11) 0.0079 (11) 0.0093 (11)C12 0.092 (2) 0.077 (2) 0.0620 (18) 0.0160 (17) 0.0096 (16) −0.0065 (15)C13 0.0641 (17) 0.088 (2) 0.0652 (18) 0.0056 (15) −0.0033 (14) 0.0320 (16)C14 0.0584 (16) 0.0727 (18) 0.0679 (18) −0.0148 (14) 0.0045 (13) 0.0154 (14)C15 0.0559 (15) 0.0806 (18) 0.0440 (14) 0.0211 (13) 0.0167 (11) 0.0238 (13)C16 0.0409 (12) 0.0466 (13) 0.0419 (13) 0.0035 (10) 0.0127 (10) 0.0067 (10)C17 0.0439 (13) 0.0447 (13) 0.0350 (12) 0.0099 (10) 0.0108 (10) 0.0094 (10)C18 0.0481 (13) 0.0527 (14) 0.0438 (13) 0.0136 (11) 0.0105 (11) 0.0111 (11)C19 0.0491 (13) 0.0489 (13) 0.0411 (13) 0.0158 (11) 0.0152 (11) 0.0151 (11)C20 0.0504 (14) 0.0530 (14) 0.0471 (14) 0.0117 (11) 0.0086 (11) 0.0076 (11)C21 0.0560 (15) 0.0455 (13) 0.0521 (14) 0.0184 (11) 0.0175 (12) 0.0092 (11)C22 0.0487 (13) 0.0494 (14) 0.0409 (12) 0.0140 (10) 0.0167 (10) 0.0202 (11)C23 0.0533 (14) 0.0534 (15) 0.0484 (14) 0.0148 (12) 0.0020 (11) 0.0108 (12)C24 0.0650 (16) 0.0494 (14) 0.0490 (14) 0.0222 (12) 0.0106 (12) 0.0102 (11)C25 0.0527 (14) 0.0565 (15) 0.0424 (13) 0.0185 (11) 0.0204 (11) 0.0223 (11)C26 0.0605 (16) 0.0606 (16) 0.0577 (16) 0.0232 (12) 0.0166 (12) 0.0200 (12)C27 0.080 (2) 0.0734 (19) 0.0688 (18) 0.0430 (17) 0.0213 (16) 0.0245 (15)C28 0.0611 (18) 0.106 (3) 0.0719 (19) 0.0418 (18) 0.0209 (15) 0.0365 (18)C29 0.0492 (15) 0.096 (2) 0.076 (2) 0.0150 (15) 0.0146 (14) 0.0374 (17)C30 0.0555 (15) 0.0686 (17) 0.0667 (17) 0.0133 (13) 0.0179 (13) 0.0326 (14)Geometric parameters (Å, °)S1—C16 1.804 (2) C12—H12C 0.9600S1—C15 1.805 (2) C13—H13A 0.9600O1—C1 1.379 (3) C13—H13B 0.9600O1—H1O 0.83 (1) C13—H13C 0.9600O2—C17 1.230 (2) C14—H14A 0.9600N1—C17 1.342 (3) C14—H14B 0.9600N1—N2 1.371 (2) C14—H14C 0.9600supplementary materialssup-5N1—H1 0.87 (1) C15—H15A 0.9700N2—C18 1.271 (3) C15—H15B 0.9700C1—C2 1.402 (3) C16—C17 1.500 (3)C1—C6 1.402 (3) C16—H16A 0.9700C2—C3 1.383 (3) C16—H16B 0.9700C2—C7 1.539 (3) C18—C19 1.462 (3)C3—C4 1.380 (3) C18—H18 0.9300C3—H3 0.9300 C19—C24 1.386 (3)C4—C5 1.379 (3) C19—C20 1.387 (3)C4—C15 1.508 (3) C20—C21 1.383 (3)C5—C6 1.387 (3) C20—H20 0.9300C5—H5 0.9300 C21—C22 1.387 (3)C6—C11 1.534 (3) C21—H21 0.9300C7—C10 1.530 (3) C22—C23 1.392 (3)C7—C9 1.540 (3) C22—C25 1.482 (3)C7—C8 1.543 (3) C23—C24 1.375 (3)C8—H8A 0.9600 C23—H23 0.9300C8—H8B 0.9600 C24—H24 0.9300C8—H8C 0.9600 C25—C30 1.387 (3)C9—H9A 0.9600 C25—C26 1.394 (3)C9—H9B 0.9600 C26—C27 1.385 (3)C9—H9C 0.9600 C26—H26 0.9300C10—H10A 0.9600 C27—C28 1.367 (4)C10—H10B 0.9600 C27—H27 0.9300C10—H10C 0.9600 C28—C29 1.363 (4)C11—C12 1.535 (3) C28—H28 0.9300C11—C14 1.536 (3) C29—C30 1.388 (3)C11—C13 1.535 (3) C29—H29 0.9300C12—H12A 0.9600 C30—H30 0.9300C12—H12B 0.9600C16—S1—C15 99.92 (10) C11—C13—H13C 109.5C1—O1—H1O 110 (4) H13A—C13—H13C 109.5C17—N1—N2 120.93 (18) H13B—C13—H13C 109.5C17—N1—H1 117.2 (14) C11—C14—H14A 109.5N2—N1—H1 121.8 (14) C11—C14—H14B 109.5C18—N2—N1 116.47 (18) H14A—C14—H14B 109.5O1—C1—C2 120.5 (2) C11—C14—H14C 109.5O1—C1—C6 116.5 (2) H14A—C14—H14C 109.5C2—C1—C6 122.98 (19) H14B—C14—H14C 109.5C3—C2—C1 116.67 (19) C4—C15—S1 109.84 (15)C3—C2—C7 121.2 (2) C4—C15—H15A 109.7C1—C2—C7 122.10 (19) S1—C15—H15A 109.7C4—C3—C2 122.6 (2) C4—C15—H15B 109.7C4—C3—H3 118.7 S1—C15—H15B 109.7C2—C3—H3 118.7 H15A—C15—H15B 108.2C5—C4—C3 118.6 (2) C17—C16—S1 109.61 (14)C5—C4—C15 120.1 (2) C17—C16—H16A 109.7C3—C4—C15 121.4 (2) S1—C16—H16A 109.7C4—C5—C6 122.6 (2) C17—C16—H16B 109.7supplementary materialssup-6C4—C5—H5 118.7 S1—C16—H16B 109.7C6—C5—H5 118.7 H16A—C16—H16B 108.2C5—C6—C1 116.5 (2) O2—C17—N1 121.11 (19)C5—C6—C11 121.18 (19) O2—C17—C16 120.80 (19)C1—C6—C11 122.28 (19) N1—C17—C16 118.04 (19)C10—C7—C9 106.5 (2) N2—C18—C19 120.3 (2)C10—C7—C2 111.37 (19) N2—C18—H18 119.8C9—C7—C2 110.51 (19) C19—C18—H18 119.8C10—C7—C8 107.4 (2) C24—C19—C20 117.8 (2)C9—C7—C8 110.5 (2) C24—C19—C18 121.9 (2)C2—C7—C8 110.45 (19) C20—C19—C18 120.2 (2)C7—C8—H8A 109.5 C21—C20—C19 120.9 (2)C7—C8—H8B 109.5 C21—C20—H20 119.5H8A—C8—H8B 109.5 C19—C20—H20 119.5C7—C8—H8C 109.5 C20—C21—C22 121.5 (2)H8A—C8—H8C 109.5 C20—C21—H21 119.3H8B—C8—H8C 109.5 C22—C21—H21 119.3C7—C9—H9A 109.5 C21—C22—C23 117.1 (2)C7—C9—H9B 109.5 C21—C22—C25 121.8 (2)H9A—C9—H9B 109.5 C23—C22—C25 121.1 (2)C7—C9—H9C 109.5 C24—C23—C22 121.6 (2)H9A—C9—H9C 109.5 C24—C23—H23 119.2H9B—C9—H9C 109.5 C22—C23—H23 119.2C7—C10—H10A 109.5 C23—C24—C19 121.1 (2)C7—C10—H10B 109.5 C23—C24—H24 119.5H10A—C10—H10B 109.5 C19—C24—H24 119.5C7—C10—H10C 109.5 C30—C25—C26 118.0 (2)H10A—C10—H10C 109.5 C30—C25—C22 121.5 (2)H10B—C10—H10C 109.5 C26—C25—C22 120.6 (2)C12—C11—C14 107.5 (2) C27—C26—C25 121.2 (3)C12—C11—C6 110.4 (2) C27—C26—H26 119.4C14—C11—C6 111.31 (19) C25—C26—H26 119.4C12—C11—C13 110.4 (2) C28—C27—C26 119.6 (3)C14—C11—C13 106.5 (2) C28—C27—H27 120.2C6—C11—C13 110.45 (19) C26—C27—H27 120.2C11—C12—H12A 109.5 C29—C28—C27 120.3 (3)C11—C12—H12B 109.5 C29—C28—H28 119.8H12A—C12—H12B 109.5 C27—C28—H28 119.8C11—C12—H12C 109.5 C28—C29—C30 120.6 (3)H12A—C12—H12C 109.5 C28—C29—H29 119.7H12B—C12—H12C 109.5 C30—C29—H29 119.7C11—C13—H13A 109.5 C25—C30—C29 120.3 (3)C11—C13—H13B 109.5 C25—C30—H30 119.9H13A—C13—H13B 109.5 C29—C30—H30 119.9Hydrogen-bond geometry (Å, °)D—H···A D—H H···A D···A D—H···AN1—H1···O2i 0.87 (1) 1.97 (1) 2.827 (2) 174 (2)supplementary materialssup-7Symmetry codes: (i) −x+1, −y+1, −z+1.Fig. 1