Ethyl 1-[2-(1,3-benzoxazol-2-ylsulfan-yl)acet-yl]-4-hy-droxy-2,6-diphenyl-1,2,5,6-tetra-hydro-pyridine-3-carboxyl-ate.

In the title compound, C(29)H(26)N(2)O(5)S, the piperidine ring adopts a half-chair conformation. The phenyl rings are oriented at dihedral angles of 75.76 (12) and 86.64 (9)° with respect to the best plane through the piperidine ring. The dihedral angle between the two phenyl rings is 30.81 (13)°. The benzoxazole ring system is approximately planar [maximum deviation = 0.016 (4) Å]. The atoms of the ethyl side chain are disordered over two sets of sites [site occupancies = 0.376 (9) and 0.624 (9)]. The mol-ecular conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond, generating an S(6) motif. The crystal packing is stabilized by inter-molecular C-H⋯O inter-actions, generating a chain running along the a axis.

Related literature

For the synthesis and biological activity of piperidin-4-one-based amides, see: Aridoss et al. (2010a ▶). For related structures see: Aridoss et al. (2010a ▶,b ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C29H26N2O5S

M = 514.58

Monoclinic,

a = 12.4630 (2) Å

b = 24.3243 (5) Å

c = 9.2350 (2) Å

β = 109.608 (1)°

V = 2637.28 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 293 K

0.23 × 0.2 × 0.18 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.963, T max = 0.971

25589 measured reflections

6571 independent reflections

4020 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.128

S = 1.05

6571 reflections

343 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811022744/lw2065sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811022744/lw2065Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811022744/lw2065Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C29H26N2O5S	F(000) = 1080
Mr = 514.58	Dx = 1.296 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1535 reflections
a = 12.4630 (2) Å	θ = 1.7–28.3°
b = 24.3243 (5) Å	µ = 0.16 mm−1
c = 9.2350 (2) Å	T = 293 K
β = 109.608 (1)°	Block, colourless
V = 2637.28 (9) Å3	0.23 × 0.2 × 0.18 mm
Z = 4

Bruker SMART APEXII area-detector diffractometer	6571 independent reflections
Radiation source: fine-focus sealed tube	4020 reflections with I > 2σ(I)
graphite	Rint = 0.033
ω and φ scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→14
Tmin = 0.963, Tmax = 0.971	k = −32→30
25589 measured reflections	l = −11→12

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0552P)2 + 0.311P] where P = (Fo2 + 2Fc2)/3
6571 reflections	(Δ/σ)max = 0.001
343 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.88932 (13)	0.51361 (7)	0.12658 (18)	0.0442 (4)
H1	0.9663	0.5002	0.1408	0.053*
C2	0.81770 (15)	0.46363 (7)	0.1329 (2)	0.0512 (4)
H2A	0.7993	0.4435	0.0369	0.061*
H2B	0.8616	0.4395	0.2150	0.061*
C3	0.71060 (14)	0.47926 (7)	0.15925 (19)	0.0490 (4)
C4	0.69728 (13)	0.52718 (7)	0.22370 (19)	0.0450 (4)
C5	0.78980 (13)	0.57022 (6)	0.27182 (19)	0.0422 (4)
H5	0.8040	0.5773	0.3811	0.051*
C6	0.75751 (15)	0.62540 (7)	0.1898 (2)	0.0519 (4)
C7	0.67108 (18)	0.63139 (9)	0.0521 (2)	0.0665 (5)
H7	0.6299	0.6007	0.0042	0.080*
C8	0.6440 (3)	0.68249 (12)	−0.0170 (3)	0.1006 (9)
H8	0.5857	0.6860	−0.1109	0.121*
C9	0.7038 (3)	0.72767 (13)	0.0541 (5)	0.1234 (12)
H9	0.6859	0.7621	0.0085	0.148*
C10	0.7896 (3)	0.72256 (11)	0.1916 (5)	0.1218 (11)
H10	0.8301	0.7535	0.2393	0.146*
C11	0.8165 (2)	0.67160 (9)	0.2602 (3)	0.0862 (7)
H11	0.8746	0.6684	0.3544	0.103*
C12	0.85080 (14)	0.54573 (7)	−0.02325 (19)	0.0457 (4)
C13	0.75318 (15)	0.53281 (8)	−0.1447 (2)	0.0553 (5)
H13	0.7080	0.5035	−0.1352	0.066*
C14	0.72199 (19)	0.56263 (9)	−0.2793 (2)	0.0685 (6)
H14	0.6555	0.5538	−0.3589	0.082*
C15	0.7888 (2)	0.60518 (9)	−0.2957 (2)	0.0739 (6)
H15	0.7682	0.6251	−0.3870	0.089*
C16	0.88687 (19)	0.61857 (9)	−0.1767 (3)	0.0710 (6)
H16	0.9327	0.6473	−0.1880	0.085*
C17	0.91674 (16)	0.58939 (8)	−0.0412 (2)	0.0567 (5)
H17	0.9820	0.5991	0.0393	0.068*
C18	0.59236 (14)	0.53668 (9)	0.2550 (2)	0.0567 (5)
C19	0.4825 (7)	0.6007 (8)	0.335 (2)	0.139 (5)	0.376 (9)
H19A	0.4214	0.5893	0.2437	0.167*	0.376 (9)
H19B	0.4691	0.5857	0.4250	0.167*	0.376 (9)
C19'	0.4874 (4)	0.6022 (5)	0.3484 (7)	0.0873 (18)	0.624 (9)
H19C	0.4396	0.5707	0.3491	0.105*	0.624 (9)
H19D	0.5043	0.6211	0.4460	0.105*	0.624 (9)
C20	0.4919 (7)	0.6599 (4)	0.3442 (17)	0.139 (5)	0.376 (9)
H20A	0.5441	0.6704	0.4430	0.209*	0.376 (9)
H20B	0.4184	0.6756	0.3303	0.209*	0.376 (9)
H20C	0.5194	0.6731	0.2651	0.209*	0.376 (9)
C20'	0.4273 (4)	0.6389 (2)	0.2241 (5)	0.0873 (18)	0.624 (9)
H20D	0.4759	0.6692	0.2210	0.131*	0.624 (9)
H20E	0.3601	0.6525	0.2406	0.131*	0.624 (9)
H20F	0.4062	0.6193	0.1283	0.131*	0.624 (9)
C21	0.99471 (13)	0.55658 (6)	0.38113 (19)	0.0401 (4)
C22	1.10534 (13)	0.53591 (7)	0.3643 (2)	0.0474 (4)
H22A	1.1021	0.5412	0.2588	0.057*
H22B	1.1121	0.4968	0.3855	0.057*
C23	1.20310 (15)	0.63370 (7)	0.4034 (2)	0.0514 (4)
C24	1.13948 (18)	0.70527 (8)	0.2721 (3)	0.0639 (5)
C25	1.2373 (2)	0.71956 (8)	0.3851 (3)	0.0685 (6)
C26	1.2833 (3)	0.77171 (11)	0.4042 (4)	0.1052 (9)
H26	1.3514	0.7803	0.4813	0.126*
C27	1.2207 (4)	0.80994 (11)	0.3007 (5)	0.1154 (11)
H27	1.2474	0.8459	0.3081	0.138*
C28	1.1209 (3)	0.79739 (11)	0.1875 (4)	0.1077 (10)
H28	1.0810	0.8249	0.1213	0.129*
C29	1.0783 (2)	0.74448 (10)	0.1695 (3)	0.0895 (7)
H29	1.0109	0.7356	0.0914	0.107*
N1	0.89780 (10)	0.54863 (5)	0.26052 (15)	0.0399 (3)
N2	1.11968 (13)	0.64910 (6)	0.2867 (2)	0.0625 (4)
O1	0.63128 (11)	0.43949 (5)	0.11907 (15)	0.0671 (4)
H1A	0.5752	0.4492	0.1399	0.101*
O2	0.51125 (11)	0.50477 (6)	0.21915 (18)	0.0791 (4)
O3	0.59263 (10)	0.58358 (6)	0.32943 (16)	0.0657 (4)
O4	0.99521 (9)	0.57867 (5)	0.50028 (14)	0.0515 (3)
O5	1.28120 (11)	0.67320 (6)	0.47306 (16)	0.0682 (4)
S1	1.22926 (4)	0.56980 (2)	0.48965 (6)	0.05622 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0438 (9)	0.0380 (9)	0.0522 (9)	0.0028 (7)	0.0179 (7)	−0.0050 (7)
C2	0.0582 (10)	0.0370 (9)	0.0556 (10)	0.0000 (8)	0.0153 (8)	−0.0023 (8)
C3	0.0471 (9)	0.0430 (10)	0.0487 (9)	−0.0077 (8)	0.0051 (8)	0.0074 (8)
C4	0.0364 (8)	0.0479 (10)	0.0479 (9)	−0.0003 (7)	0.0105 (7)	0.0088 (8)
C5	0.0376 (8)	0.0429 (9)	0.0481 (9)	0.0010 (7)	0.0171 (7)	−0.0014 (7)
C6	0.0500 (10)	0.0413 (10)	0.0728 (12)	0.0085 (8)	0.0316 (9)	0.0024 (9)
C7	0.0801 (14)	0.0556 (13)	0.0687 (13)	0.0182 (10)	0.0313 (11)	0.0113 (10)
C8	0.128 (2)	0.0773 (19)	0.1017 (19)	0.0435 (18)	0.0454 (17)	0.0357 (16)
C9	0.147 (3)	0.0582 (19)	0.180 (4)	0.0325 (19)	0.075 (3)	0.044 (2)
C10	0.116 (2)	0.0432 (15)	0.205 (4)	−0.0003 (15)	0.052 (2)	0.0068 (19)
C11	0.0755 (15)	0.0451 (13)	0.133 (2)	0.0010 (11)	0.0281 (14)	−0.0042 (13)
C12	0.0493 (9)	0.0432 (10)	0.0493 (10)	0.0051 (8)	0.0228 (8)	−0.0043 (8)
C13	0.0589 (11)	0.0577 (12)	0.0508 (10)	0.0008 (9)	0.0202 (9)	−0.0053 (9)
C14	0.0766 (14)	0.0754 (15)	0.0498 (11)	0.0106 (12)	0.0163 (10)	−0.0018 (10)
C15	0.1025 (17)	0.0696 (15)	0.0538 (12)	0.0213 (13)	0.0318 (12)	0.0106 (11)
C16	0.0895 (15)	0.0556 (13)	0.0783 (15)	0.0004 (11)	0.0418 (13)	0.0099 (11)
C17	0.0603 (11)	0.0507 (11)	0.0621 (11)	−0.0005 (9)	0.0244 (9)	0.0013 (9)
C18	0.0408 (9)	0.0696 (13)	0.0564 (11)	0.0021 (9)	0.0121 (8)	0.0154 (10)
C19	0.060 (4)	0.129 (7)	0.253 (11)	−0.009 (4)	0.084 (6)	−0.055 (7)
C19'	0.067 (2)	0.126 (4)	0.074 (2)	0.0404 (19)	0.0303 (17)	0.0150 (18)
C20	0.060 (4)	0.129 (7)	0.253 (11)	−0.009 (4)	0.084 (6)	−0.055 (7)
C20'	0.067 (2)	0.126 (4)	0.074 (2)	0.0404 (19)	0.0303 (17)	0.0150 (18)
C21	0.0398 (8)	0.0328 (8)	0.0483 (9)	−0.0017 (6)	0.0156 (7)	0.0060 (7)
C22	0.0414 (9)	0.0384 (9)	0.0632 (11)	0.0018 (7)	0.0187 (8)	0.0064 (8)
C23	0.0487 (10)	0.0480 (10)	0.0617 (11)	−0.0084 (8)	0.0240 (9)	0.0026 (9)
C24	0.0726 (13)	0.0475 (12)	0.0816 (14)	−0.0018 (10)	0.0390 (11)	0.0110 (10)
C25	0.0927 (16)	0.0431 (11)	0.0836 (15)	−0.0089 (11)	0.0482 (13)	−0.0039 (11)
C26	0.142 (2)	0.0591 (17)	0.128 (2)	−0.0321 (17)	0.062 (2)	−0.0240 (16)
C27	0.174 (3)	0.0439 (16)	0.161 (3)	−0.009 (2)	0.101 (3)	−0.0040 (19)
C28	0.153 (3)	0.0565 (17)	0.150 (3)	0.0250 (18)	0.099 (2)	0.0374 (18)
C29	0.1020 (18)	0.0645 (15)	0.1127 (19)	0.0125 (13)	0.0501 (15)	0.0317 (14)
N1	0.0372 (7)	0.0358 (7)	0.0476 (8)	0.0018 (6)	0.0154 (6)	−0.0017 (6)
N2	0.0595 (9)	0.0480 (10)	0.0755 (11)	−0.0059 (8)	0.0168 (8)	0.0175 (8)
O1	0.0599 (8)	0.0576 (8)	0.0738 (9)	−0.0203 (6)	0.0092 (7)	0.0000 (7)
O2	0.0411 (7)	0.0926 (11)	0.0999 (11)	−0.0139 (7)	0.0189 (7)	0.0082 (9)
O3	0.0448 (7)	0.0847 (10)	0.0738 (9)	0.0084 (7)	0.0280 (6)	0.0025 (8)
O4	0.0459 (6)	0.0572 (8)	0.0505 (7)	−0.0026 (5)	0.0148 (5)	−0.0073 (6)
O5	0.0700 (9)	0.0599 (9)	0.0748 (9)	−0.0195 (7)	0.0246 (7)	−0.0099 (7)
S1	0.0396 (2)	0.0558 (3)	0.0685 (3)	−0.0013 (2)	0.0118 (2)	0.0148 (2)

C1—N1	1.476 (2)	C18—O3	1.331 (2)
C1—C12	1.520 (2)	C19—C20	1.44 (2)
C1—C2	1.521 (2)	C19—O3	1.453 (3)
C1—H1	0.9800	C19—H19A	0.9700
C2—C3	1.484 (2)	C19—H19B	0.9700
C2—H2A	0.9700	C19'—C20'	1.449 (9)
C2—H2B	0.9700	C19'—O3	1.453 (2)
C3—O1	1.3434 (19)	C19'—H19C	0.9700
C3—C4	1.344 (2)	C19'—H19D	0.9700
C4—C18	1.449 (2)	C20—H20A	0.9600
C4—C5	1.510 (2)	C20—H20B	0.9600
C5—N1	1.4807 (19)	C20—H20C	0.9600
C5—C6	1.527 (2)	C20'—H20D	0.9600
C5—H5	0.9800	C20'—H20E	0.9600
C6—C7	1.371 (3)	C20'—H20F	0.9600
C6—C11	1.380 (3)	C21—O4	1.2226 (19)
C7—C8	1.386 (3)	C21—N1	1.354 (2)
C7—H7	0.9300	C21—C22	1.524 (2)
C8—C9	1.366 (4)	C22—S1	1.7901 (17)
C8—H8	0.9300	C22—H22A	0.9700
C9—C10	1.364 (4)	C22—H22B	0.9700
C9—H9	0.9300	C23—N2	1.277 (2)
C10—C11	1.381 (4)	C23—O5	1.365 (2)
C10—H10	0.9300	C23—S1	1.7271 (19)
C11—H11	0.9300	C24—C25	1.357 (3)
C12—C13	1.386 (2)	C24—C29	1.380 (3)
C12—C17	1.387 (2)	C24—N2	1.403 (2)
C13—C14	1.377 (3)	C25—C26	1.379 (3)
C13—H13	0.9300	C25—O5	1.390 (3)
C14—C15	1.369 (3)	C26—C27	1.374 (4)
C14—H14	0.9300	C26—H26	0.9300
C15—C16	1.381 (3)	C27—C28	1.363 (4)
C15—H15	0.9300	C27—H27	0.9300
C16—C17	1.376 (3)	C28—C29	1.381 (4)
C16—H16	0.9300	C28—H28	0.9300
C17—H17	0.9300	C29—H29	0.9300
C18—O2	1.229 (2)	O1—H1A	0.8200
N1—C1—C12	112.22 (13)	O2—C18—C4	124.2 (2)
N1—C1—C2	107.88 (13)	O3—C18—C4	113.17 (16)
C12—C1—C2	115.83 (14)	C20—C19—O3	103.2 (10)
N1—C1—H1	106.8	C20—C19—H19A	111.1
C12—C1—H1	106.8	O3—C19—H19A	111.1
C2—C1—H1	106.8	C20—C19—H19B	111.1
C3—C2—C1	111.90 (14)	O3—C19—H19B	111.1
C3—C2—H2A	109.2	H19A—C19—H19B	109.1
C1—C2—H2A	109.2	C20'—C19'—O3	110.1 (4)
C3—C2—H2B	109.2	C20'—C19'—H19C	109.6
C1—C2—H2B	109.2	O3—C19'—H19C	109.6
H2A—C2—H2B	107.9	C20'—C19'—H19D	109.6
O1—C3—C4	123.92 (16)	O3—C19'—H19D	109.6
O1—C3—C2	112.90 (15)	H19C—C19'—H19D	108.2
C4—C3—C2	123.11 (15)	C19'—C20'—H20D	109.5
C3—C4—C18	118.71 (16)	C19'—C20'—H20E	109.5
C3—C4—C5	122.42 (14)	H20D—C20'—H20E	109.5
C18—C4—C5	118.80 (16)	C19'—C20'—H20F	109.5
N1—C5—C4	110.84 (13)	H20D—C20'—H20F	109.5
N1—C5—C6	111.79 (13)	H20E—C20'—H20F	109.5
C4—C5—C6	114.55 (13)	O4—C21—N1	122.46 (14)
N1—C5—H5	106.4	O4—C21—C22	120.34 (14)
C4—C5—H5	106.4	N1—C21—C22	117.19 (14)
C6—C5—H5	106.4	C21—C22—S1	113.33 (12)
C7—C6—C11	118.61 (19)	C21—C22—H22A	108.9
C7—C6—C5	123.21 (17)	S1—C22—H22A	108.9
C11—C6—C5	118.16 (18)	C21—C22—H22B	108.9
C6—C7—C8	121.1 (2)	S1—C22—H22B	108.9
C6—C7—H7	119.5	H22A—C22—H22B	107.7
C8—C7—H7	119.5	N2—C23—O5	116.17 (16)
C9—C8—C7	119.4 (3)	N2—C23—S1	128.87 (14)
C9—C8—H8	120.3	O5—C23—S1	114.93 (13)
C7—C8—H8	120.3	C25—C24—C29	119.9 (2)
C10—C9—C8	120.3 (3)	C25—C24—N2	108.47 (18)
C10—C9—H9	119.8	C29—C24—N2	131.7 (2)
C8—C9—H9	119.8	C24—C25—C26	124.2 (2)
C9—C10—C11	120.2 (3)	C24—C25—O5	108.52 (17)
C9—C10—H10	119.9	C26—C25—O5	127.3 (2)
C11—C10—H10	119.9	C27—C26—C25	114.7 (3)
C6—C11—C10	120.4 (3)	C27—C26—H26	122.6
C6—C11—H11	119.8	C25—C26—H26	122.6
C10—C11—H11	119.8	C28—C27—C26	122.8 (3)
C13—C12—C17	118.11 (17)	C28—C27—H27	118.6
C13—C12—C1	122.93 (16)	C26—C27—H27	118.6
C17—C12—C1	118.95 (15)	C27—C28—C29	121.1 (3)
C14—C13—C12	121.07 (19)	C27—C28—H28	119.5
C14—C13—H13	119.5	C29—C28—H28	119.5
C12—C13—H13	119.5	C24—C29—C28	117.4 (3)
C15—C14—C13	120.0 (2)	C24—C29—H29	121.3
C15—C14—H14	120.0	C28—C29—H29	121.3
C13—C14—H14	120.0	C21—N1—C1	124.39 (13)
C14—C15—C16	119.9 (2)	C21—N1—C5	118.19 (13)
C14—C15—H15	120.0	C1—N1—C5	116.91 (12)
C16—C15—H15	120.0	C23—N2—C24	104.33 (17)
C17—C16—C15	119.9 (2)	C3—O1—H1A	109.5
C17—C16—H16	120.0	C18—O3—C19'	118.9 (5)
C15—C16—H16	120.0	C18—O3—C19	115.3 (7)
C16—C17—C12	120.89 (19)	C19'—O3—C19	4.8 (9)
C16—C17—H17	119.6	C23—O5—C25	102.52 (15)
C12—C17—H17	119.6	C23—S1—C22	97.35 (8)
O2—C18—O3	122.67 (17)
N1—C1—C2—C3	48.57 (18)	C29—C24—C25—C26	−1.5 (3)
C12—C1—C2—C3	−78.14 (18)	N2—C24—C25—C26	179.3 (2)
C1—C2—C3—O1	160.73 (14)	C29—C24—C25—O5	179.21 (19)
C1—C2—C3—C4	−22.4 (2)	N2—C24—C25—O5	0.0 (2)
O1—C3—C4—C18	1.2 (2)	C24—C25—C26—C27	1.5 (4)
C2—C3—C4—C18	−175.36 (15)	O5—C25—C26—C27	−179.4 (2)
O1—C3—C4—C5	178.08 (15)	C25—C26—C27—C28	−0.1 (4)
C2—C3—C4—C5	1.5 (3)	C26—C27—C28—C29	−1.1 (5)
C3—C4—C5—N1	−8.7 (2)	C25—C24—C29—C28	0.2 (3)
C18—C4—C5—N1	168.15 (13)	N2—C24—C29—C28	179.2 (2)
C3—C4—C5—C6	118.88 (17)	C27—C28—C29—C24	1.1 (4)
C18—C4—C5—C6	−64.23 (19)	O4—C21—N1—C1	−168.31 (15)
N1—C5—C6—C7	106.37 (18)	C22—C21—N1—C1	10.7 (2)
C4—C5—C6—C7	−20.8 (2)	O4—C21—N1—C5	3.2 (2)
N1—C5—C6—C11	−75.4 (2)	C22—C21—N1—C5	−177.75 (13)
C4—C5—C6—C11	157.43 (17)	C12—C1—N1—C21	−120.16 (16)
C11—C6—C7—C8	1.0 (3)	C2—C1—N1—C21	111.06 (16)
C5—C6—C7—C8	179.19 (19)	C12—C1—N1—C5	68.23 (17)
C6—C7—C8—C9	−0.6 (4)	C2—C1—N1—C5	−60.56 (17)
C7—C8—C9—C10	0.2 (5)	C4—C5—N1—C21	−132.40 (14)
C8—C9—C10—C11	−0.2 (5)	C6—C5—N1—C21	98.49 (17)
C7—C6—C11—C10	−0.9 (3)	C4—C5—N1—C1	39.75 (18)
C5—C6—C11—C10	−179.2 (2)	C6—C5—N1—C1	−89.36 (17)
C9—C10—C11—C6	0.5 (5)	O5—C23—N2—C24	−0.5 (2)
N1—C1—C12—C13	−120.99 (16)	S1—C23—N2—C24	177.45 (15)
C2—C1—C12—C13	3.5 (2)	C25—C24—N2—C23	0.3 (2)
N1—C1—C12—C17	60.14 (19)	C29—C24—N2—C23	−178.8 (2)
C2—C1—C12—C17	−175.36 (15)	O2—C18—O3—C19'	−9.8 (4)
C17—C12—C13—C14	−0.4 (3)	C4—C18—O3—C19'	171.1 (3)
C1—C12—C13—C14	−179.27 (16)	O2—C18—O3—C19	−13.3 (10)
C12—C13—C14—C15	1.2 (3)	C4—C18—O3—C19	167.7 (10)
C13—C14—C15—C16	−0.7 (3)	C20'—C19'—O3—C18	−93.0 (8)
C14—C15—C16—C17	−0.5 (3)	C20'—C19'—O3—C19	−52 (15)
C15—C16—C17—C12	1.3 (3)	C20—C19—O3—C18	−151.2 (9)
C13—C12—C17—C16	−0.9 (3)	C20—C19—O3—C19'	69 (15)
C1—C12—C17—C16	178.06 (16)	N2—C23—O5—C25	0.5 (2)
C3—C4—C18—O2	−3.9 (3)	S1—C23—O5—C25	−177.77 (13)
C5—C4—C18—O2	179.06 (17)	C24—C25—O5—C23	−0.2 (2)
C3—C4—C18—O3	175.12 (15)	C26—C25—O5—C23	−179.5 (2)
C5—C4—C18—O3	−1.9 (2)	N2—C23—S1—C22	−0.05 (19)
O4—C21—C22—S1	−23.5 (2)	O5—C23—S1—C22	177.90 (13)
N1—C21—C22—S1	157.47 (12)	C21—C22—S1—C23	−68.22 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	1.84	2.558 (2)	145
C13—H13···O2i	0.93	2.59	3.263 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.82	1.84	2.558 (2)	145
C13—H13⋯O2i	0.93	2.59	3.263 (2)	130

Symmetry code: (i) .