(2RS,5RS,6RS)-Ethyl 4-hydr­oxy-2,6-di-p-tolyl-5-p-tolyl­sulfanyl-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

The polysubstituted piperidine enol ring in the title compound, C₂₉H₃₁NO₃S, adopts a twisted half-chair conformation. The crystal structure is stabilized by van der Waals and weak C—H...π inter­actions. An intra­molecular O—H...O inter­action generates an S(6) graph-set motif.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.146
• Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O1     -   C4      ..      12.19 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C3     -   C7      ..       7.71 su
PLAT411_ALERT_2_B Short Inter H...H Contact  H8B    ..  H8B     ..       2.01 Ang.

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT128_ALERT_4_C Non-standard setting of Space group C2/c    ....    I2/a
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.55 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.69 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C24
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C51
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C54
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1     ...          ?

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(2RS,5RS,6RS)-Ethyl 4-hydroxy-2,6-di-p-tolyl-5-p-tolylsulfanyl- 1,2,5,6-tetrahydropyridine-3-carboxylate

Crystal data

C29H31NO3S	F(000) = 2016
Mr = 473.61	Dx = 1.197 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 12.7293 (7) Å	Cell parameters from 25 reflections
b = 10.4916 (12) Å	θ = 2–25°
c = 39.6468 (10) Å	µ = 0.15 mm^−1
β = 96.990 (11)°	T = 293 K
V = 5255.5 (7) Å^3	Block, colourless
Z = 8	0.18 × 0.16 × 0.12 mm

Data collection

Nonius MACH-3 four-circle diffractometer	2240 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.037
Graphite monochromator	θmax = 25.0°, θmin = 2.0°
ω scans	h = −14→15
Absorption correction: ψ scan (North et al., 1968)	k = −1→12
Tmin = 0.969, Tmax = 0.982	l = −14→47
5261 measured reflections	3 standard reflections every 60 min
4639 independent reflections	intensity decay: none

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0693P)^2 + 2.001P] where P = (Fo^2 + 2Fc^2)/3
4639 reflections	(Δ/σ)max = 0.001
316 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
C2	0.45209 (19)	0.1153 (2)	0.09155 (7)	0.0488 (6)
H2	0.4374	0.0465	0.0749	0.059*
C3	0.5714 (2)	0.1288 (2)	0.09768 (7)	0.0510 (7)
C4	0.6229 (2)	0.1383 (2)	0.12970 (8)	0.0557 (7)
C5	0.5659 (2)	0.1433 (2)	0.16078 (7)	0.0585 (7)
H5	0.5784	0.0605	0.1720	0.070*
C6	0.4455 (2)	0.1549 (2)	0.15219 (7)	0.0521 (7)
H6	0.4279	0.2430	0.1456	0.063*
C7	0.6305 (2)	0.1220 (3)	0.06915 (9)	0.0651 (8)
C8	0.6172 (3)	0.1197 (4)	0.00845 (9)	0.0882 (11)
H8A	0.6283	0.0322	0.0018	0.106*
H8B	0.6857	0.1613	0.0124	0.106*
C9	0.5503 (3)	0.1857 (4)	−0.01877 (10)	0.1007 (12)
H9A	0.5369	0.2710	−0.0117	0.151*
H9B	0.4844	0.1410	−0.0236	0.151*
H9C	0.5856	0.1882	−0.0388	0.151*
C21	0.39232 (19)	0.2320 (2)	0.07651 (6)	0.0474 (6)
C22	0.2966 (2)	0.2148 (3)	0.05642 (8)	0.0680 (8)
H22	0.2732	0.1327	0.0508	0.082*
C23	0.2355 (3)	0.3180 (4)	0.04463 (9)	0.0834 (10)
H23	0.1717	0.3037	0.0311	0.100*
C24	0.2663 (3)	0.4414 (3)	0.05238 (9)	0.0753 (9)
C25	0.3625 (3)	0.4579 (3)	0.07159 (8)	0.0712 (9)
H25	0.3865	0.5402	0.0769	0.085*
C26	0.4247 (2)	0.3554 (3)	0.08331 (7)	0.0593 (7)
H26	0.4899	0.3701	0.0961	0.071*
C27	0.1938 (3)	0.5527 (4)	0.04086 (11)	0.1205 (16)
H27A	0.2325	0.6311	0.0442	0.181*
H27B	0.1350	0.5541	0.0539	0.181*
H27C	0.1681	0.5430	0.0172	0.181*
C51	0.5961 (2)	0.4097 (3)	0.16969 (7)	0.0559 (7)
C52	0.5131 (3)	0.4864 (3)	0.17575 (9)	0.0788 (9)
H52	0.4666	0.4596	0.1907	0.095*
C53	0.4982 (3)	0.6039 (3)	0.15978 (10)	0.0855 (11)
H53	0.4415	0.6546	0.1642	0.103*
C54	0.5649 (3)	0.6471 (3)	0.13754 (8)	0.0706 (8)
C55	0.6480 (2)	0.5696 (3)	0.13191 (8)	0.0671 (8)
H55	0.6947	0.5965	0.1170	0.080*
C56	0.6642 (2)	0.4528 (3)	0.14776 (8)	0.0624 (8)
H56	0.7216	0.4028	0.1436	0.075*
C57	0.5500 (4)	0.7758 (3)	0.12013 (11)	0.1141 (14)
H57A	0.6101	0.8289	0.1272	0.171*
H57B	0.4871	0.8155	0.1262	0.171*
H57C	0.5436	0.7642	0.0959	0.171*
C61	0.3834 (2)	0.1171 (2)	0.18070 (7)	0.0542 (7)
C62	0.4034 (2)	0.0057 (3)	0.19947 (7)	0.0643 (8)
H62	0.4602	−0.0457	0.1955	0.077*
C63	0.3408 (3)	−0.0297 (3)	0.22379 (8)	0.0712 (9)
H63	0.3567	−0.1042	0.2361	0.085*
C64	0.2549 (3)	0.0424 (3)	0.23048 (7)	0.0685 (8)
C65	0.2345 (3)	0.1527 (3)	0.21165 (8)	0.0758 (9)
H65	0.1769	0.2032	0.2154	0.091*
C66	0.2980 (2)	0.1890 (3)	0.18747 (8)	0.0672 (8)
H66	0.2827	0.2641	0.1754	0.081*
C67	0.1854 (3)	0.0030 (4)	0.25703 (8)	0.0932 (11)
H67A	0.1200	0.0495	0.2536	0.140*
H67B	0.2210	0.0214	0.2793	0.140*
H67C	0.1711	−0.0867	0.2551	0.140*
N1	0.4145 (2)	0.0707 (2)	0.12301 (6)	0.0514 (6)
O1	0.73162 (18)	0.1402 (3)	0.13714 (7)	0.1051 (8)
H1A	0.7588	0.1304	0.1196	0.158*
O2	0.72698 (16)	0.1173 (2)	0.06965 (6)	0.0831 (7)
O3	0.56696 (15)	0.1217 (2)	0.03906 (6)	0.0751 (6)
S1	0.61819 (7)	0.26291 (8)	0.19199 (2)	0.0750 (3)
H1	0.348 (2)	0.067 (2)	0.1201 (6)	0.049 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0459 (15)	0.0443 (15)	0.0574 (17)	−0.0040 (12)	0.0107 (12)	−0.0061 (13)
C3	0.0458 (15)	0.0388 (14)	0.0694 (19)	0.0030 (12)	0.0110 (14)	0.0002 (14)
C4	0.0425 (15)	0.0363 (15)	0.086 (2)	0.0043 (12)	0.0000 (15)	0.0017 (14)
C5	0.0604 (18)	0.0407 (15)	0.0712 (19)	−0.0012 (13)	−0.0044 (15)	0.0029 (14)
C6	0.0595 (17)	0.0395 (14)	0.0563 (17)	0.0012 (13)	0.0024 (13)	0.0017 (13)
C7	0.0568 (19)	0.0480 (17)	0.091 (2)	0.0027 (15)	0.0118 (18)	−0.0013 (16)
C8	0.077 (2)	0.108 (3)	0.087 (3)	−0.001 (2)	0.037 (2)	−0.008 (2)
C9	0.114 (3)	0.107 (3)	0.084 (3)	−0.012 (3)	0.023 (2)	−0.003 (2)
C21	0.0418 (14)	0.0488 (16)	0.0528 (15)	−0.0029 (12)	0.0104 (12)	−0.0002 (13)
C22	0.0569 (18)	0.065 (2)	0.079 (2)	−0.0058 (16)	−0.0024 (16)	0.0004 (17)
C23	0.0538 (19)	0.101 (3)	0.091 (3)	0.006 (2)	−0.0079 (17)	0.019 (2)
C24	0.072 (2)	0.074 (2)	0.082 (2)	0.0197 (19)	0.0194 (18)	0.0223 (19)
C25	0.079 (2)	0.0535 (18)	0.081 (2)	0.0028 (17)	0.0126 (18)	0.0095 (16)
C26	0.0562 (17)	0.0506 (17)	0.0703 (19)	−0.0022 (14)	0.0043 (14)	0.0048 (15)
C27	0.112 (3)	0.117 (3)	0.136 (4)	0.059 (3)	0.026 (3)	0.049 (3)
C51	0.0594 (17)	0.0484 (16)	0.0586 (17)	−0.0060 (14)	0.0019 (14)	−0.0077 (14)
C52	0.075 (2)	0.071 (2)	0.097 (2)	−0.0102 (19)	0.0321 (18)	−0.014 (2)
C53	0.074 (2)	0.058 (2)	0.128 (3)	0.0128 (18)	0.024 (2)	−0.015 (2)
C54	0.076 (2)	0.0503 (18)	0.084 (2)	0.0023 (17)	0.0039 (18)	−0.0079 (17)
C55	0.075 (2)	0.0518 (18)	0.076 (2)	−0.0083 (16)	0.0176 (16)	−0.0053 (16)
C56	0.0541 (17)	0.0521 (18)	0.081 (2)	0.0009 (14)	0.0096 (16)	−0.0092 (16)
C57	0.144 (4)	0.058 (2)	0.137 (4)	0.017 (2)	0.004 (3)	0.010 (2)
C61	0.0598 (17)	0.0457 (16)	0.0557 (17)	−0.0016 (14)	0.0017 (13)	−0.0020 (13)
C62	0.0684 (19)	0.0578 (18)	0.0669 (19)	0.0105 (15)	0.0091 (16)	0.0090 (16)
C63	0.083 (2)	0.069 (2)	0.0601 (19)	−0.0010 (18)	0.0046 (17)	0.0121 (16)
C64	0.073 (2)	0.079 (2)	0.0533 (18)	−0.0083 (19)	0.0040 (15)	−0.0072 (17)
C65	0.071 (2)	0.082 (2)	0.077 (2)	0.0142 (18)	0.0177 (18)	−0.0032 (19)
C66	0.073 (2)	0.0593 (18)	0.070 (2)	0.0118 (17)	0.0106 (17)	0.0079 (16)
C67	0.095 (3)	0.119 (3)	0.069 (2)	−0.013 (2)	0.0229 (19)	0.004 (2)
N1	0.0488 (14)	0.0435 (13)	0.0617 (15)	−0.0027 (11)	0.0056 (12)	−0.0008 (11)
O1	0.0735 (16)	0.0908 (18)	0.147 (2)	0.0100 (14)	−0.0015 (15)	0.0041 (19)
O2	0.0493 (12)	0.0905 (17)	0.1127 (18)	0.0116 (12)	0.0229 (12)	0.0049 (14)
O3	0.0566 (12)	0.0958 (16)	0.0769 (15)	−0.0003 (11)	0.0254 (11)	−0.0089 (13)
S1	0.0887 (6)	0.0617 (5)	0.0689 (5)	−0.0147 (4)	−0.0135 (4)	0.0031 (4)

Geometric parameters (Å, º)

C2—N1	1.466 (3)	C27—H27A	0.9600
C2—C3	1.516 (3)	C27—H27B	0.9600
C2—C21	1.525 (4)	C27—H27C	0.9600
C2—H2	0.9800	C51—C52	1.372 (4)
C3—C4	1.360 (4)	C51—C56	1.377 (4)
C3—C7	1.434 (4)	C51—S1	1.781 (3)
C4—O1	1.379 (3)	C52—C53	1.388 (5)
C4—C5	1.505 (4)	C52—H52	0.9300
C5—C6	1.533 (4)	C53—C54	1.374 (5)
C5—S1	1.830 (3)	C53—H53	0.9300
C5—H5	0.9800	C54—C55	1.375 (4)
C6—N1	1.471 (3)	C54—C57	1.517 (4)
C6—C61	1.509 (4)	C55—C56	1.381 (4)
C6—H6	0.9800	C55—H55	0.9300
C7—O2	1.227 (3)	C56—H56	0.9300
C7—O3	1.357 (4)	C57—H57A	0.9600
C8—O3	1.439 (4)	C57—H57B	0.9600
C8—C9	1.465 (5)	C57—H57C	0.9600
C8—H8A	0.9700	C61—C66	1.376 (4)
C8—H8B	0.9700	C61—C62	1.392 (4)
C9—H9A	0.9600	C62—C63	1.375 (4)
C9—H9B	0.9600	C62—H62	0.9300
C9—H9C	0.9600	C63—C64	1.381 (4)
C21—C26	1.375 (4)	C63—H63	0.9300
C21—C22	1.384 (4)	C64—C65	1.385 (4)
C22—C23	1.381 (4)	C64—C67	1.513 (4)
C22—H22	0.9300	C65—C66	1.381 (4)
C23—C24	1.377 (5)	C65—H65	0.9300
C23—H23	0.9300	C66—H66	0.9300
C24—C25	1.372 (5)	C67—H67A	0.9600
C24—C27	1.524 (4)	C67—H67B	0.9600
C25—C26	1.383 (4)	C67—H67C	0.9600
C25—H25	0.9300	N1—H1	0.84 (2)
C26—H26	0.9300	O1—H1A	0.8200
N1—C2—C3	108.5 (2)	H27A—C27—H27B	109.5
N1—C2—C21	113.0 (2)	C24—C27—H27C	109.5
C3—C2—C21	115.5 (2)	H27A—C27—H27C	109.5
N1—C2—H2	106.4	H27B—C27—H27C	109.5
C3—C2—H2	106.4	C52—C51—C56	118.4 (3)
C21—C2—H2	106.4	C52—C51—S1	119.9 (2)
C4—C3—C7	120.0 (3)	C56—C51—S1	121.6 (2)
C4—C3—C2	121.1 (2)	C51—C52—C53	120.5 (3)
C7—C3—C2	118.7 (3)	C51—C52—H52	119.8
C3—C4—O1	123.9 (3)	C53—C52—H52	119.8
C3—C4—C5	122.8 (2)	C54—C53—C52	121.6 (3)
O1—C4—C5	113.3 (3)	C54—C53—H53	119.2
C4—C5—C6	112.9 (2)	C52—C53—H53	119.2
C4—C5—S1	113.90 (19)	C53—C54—C55	117.2 (3)
C6—C5—S1	111.53 (19)	C53—C54—C57	122.2 (3)
C4—C5—H5	105.9	C55—C54—C57	120.6 (3)
C6—C5—H5	105.9	C54—C55—C56	121.8 (3)
S1—C5—H5	105.9	C54—C55—H55	119.1
N1—C6—C61	108.4 (2)	C56—C55—H55	119.1
N1—C6—C5	107.0 (2)	C51—C56—C55	120.5 (3)
C61—C6—C5	114.4 (2)	C51—C56—H56	119.7
N1—C6—H6	109.0	C55—C56—H56	119.7
C61—C6—H6	109.0	C54—C57—H57A	109.5
C5—C6—H6	109.0	C54—C57—H57B	109.5
O2—C7—O3	120.2 (3)	H57A—C57—H57B	109.5
O2—C7—C3	127.5 (3)	C54—C57—H57C	109.5
O3—C7—C3	112.3 (3)	H57A—C57—H57C	109.5
O3—C8—C9	109.6 (3)	H57B—C57—H57C	109.5
O3—C8—H8A	109.8	C66—C61—C62	117.0 (3)
C9—C8—H8A	109.8	C66—C61—C6	120.0 (3)
O3—C8—H8B	109.8	C62—C61—C6	122.9 (3)
C9—C8—H8B	109.8	C63—C62—C61	121.2 (3)
H8A—C8—H8B	108.2	C63—C62—H62	119.4
C8—C9—H9A	109.5	C61—C62—H62	119.4
C8—C9—H9B	109.5	C62—C63—C64	121.8 (3)
H9A—C9—H9B	109.5	C62—C63—H63	119.1
C8—C9—H9C	109.5	C64—C63—H63	119.1
H9A—C9—H9C	109.5	C63—C64—C65	117.1 (3)
H9B—C9—H9C	109.5	C63—C64—C67	121.9 (3)
C26—C21—C22	117.2 (3)	C65—C64—C67	121.0 (3)
C26—C21—C2	123.8 (2)	C66—C65—C64	121.1 (3)
C22—C21—C2	118.9 (2)	C66—C65—H65	119.4
C23—C22—C21	120.9 (3)	C64—C65—H65	119.4
C23—C22—H22	119.6	C61—C66—C65	121.8 (3)
C21—C22—H22	119.6	C61—C66—H66	119.1
C24—C23—C22	121.9 (3)	C65—C66—H66	119.1
C24—C23—H23	119.1	C64—C67—H67A	109.5
C22—C23—H23	119.1	C64—C67—H67B	109.5
C25—C24—C23	117.0 (3)	H67A—C67—H67B	109.5
C25—C24—C27	122.5 (4)	C64—C67—H67C	109.5
C23—C24—C27	120.5 (3)	H67A—C67—H67C	109.5
C24—C25—C26	121.6 (3)	H67B—C67—H67C	109.5
C24—C25—H25	119.2	C2—N1—C6	113.2 (2)
C26—C25—H25	119.2	C2—N1—H1	108.7 (17)
C21—C26—C25	121.4 (3)	C6—N1—H1	107.8 (18)
C21—C26—H26	119.3	C4—O1—H1A	109.5
C25—C26—H26	119.3	C7—O3—C8	117.6 (2)
C24—C27—H27A	109.5	C51—S1—C5	103.59 (13)
C24—C27—H27B	109.5
N1—C2—C3—C4	−19.5 (3)	S1—C51—C52—C53	176.8 (3)
C21—C2—C3—C4	108.5 (3)	C51—C52—C53—C54	0.1 (5)
N1—C2—C3—C7	155.9 (2)	C52—C53—C54—C55	−0.5 (5)
C21—C2—C3—C7	−76.1 (3)	C52—C53—C54—C57	−179.5 (3)
C7—C3—C4—O1	−1.0 (4)	C53—C54—C55—C56	0.2 (5)
C2—C3—C4—O1	174.4 (3)	C57—C54—C55—C56	179.2 (3)
C7—C3—C4—C5	−178.8 (2)	C52—C51—C56—C55	−1.0 (4)
C2—C3—C4—C5	−3.4 (4)	S1—C51—C56—C55	−177.1 (2)
C3—C4—C5—C6	−7.9 (4)	C54—C55—C56—C51	0.6 (4)
O1—C4—C5—C6	174.1 (2)	N1—C6—C61—C66	−102.8 (3)
C3—C4—C5—S1	−136.4 (2)	C5—C6—C61—C66	137.9 (3)
O1—C4—C5—S1	45.6 (3)	N1—C6—C61—C62	72.4 (3)
C4—C5—C6—N1	40.7 (3)	C5—C6—C61—C62	−46.9 (4)
S1—C5—C6—N1	170.42 (17)	C66—C61—C62—C63	−0.5 (4)
C4—C5—C6—C61	160.8 (2)	C6—C61—C62—C63	−175.7 (3)
S1—C5—C6—C61	−69.5 (3)	C61—C62—C63—C64	0.7 (5)
C4—C3—C7—O2	3.9 (4)	C62—C63—C64—C65	−0.2 (5)
C2—C3—C7—O2	−171.6 (3)	C62—C63—C64—C67	179.5 (3)
C4—C3—C7—O3	−175.7 (2)	C63—C64—C65—C66	−0.5 (5)
C2—C3—C7—O3	8.8 (3)	C67—C64—C65—C66	179.8 (3)
N1—C2—C21—C26	92.8 (3)	C62—C61—C66—C65	−0.2 (4)
C3—C2—C21—C26	−32.9 (4)	C6—C61—C66—C65	175.2 (3)
N1—C2—C21—C22	−83.2 (3)	C64—C65—C66—C61	0.7 (5)
C3—C2—C21—C22	151.0 (3)	C3—C2—N1—C6	57.0 (3)
C26—C21—C22—C23	−1.8 (4)	C21—C2—N1—C6	−72.4 (3)
C2—C21—C22—C23	174.5 (3)	C61—C6—N1—C2	167.6 (2)
C21—C22—C23—C24	−0.4 (5)	C5—C6—N1—C2	−68.6 (3)
C22—C23—C24—C25	2.0 (5)	O2—C7—O3—C8	−1.8 (4)
C22—C23—C24—C27	−176.1 (3)	C3—C7—O3—C8	177.9 (3)
C23—C24—C25—C26	−1.4 (5)	C9—C8—O3—C7	−149.9 (3)
C27—C24—C25—C26	176.5 (3)	C52—C51—S1—C5	102.3 (3)
C22—C21—C26—C25	2.3 (4)	C56—C51—S1—C5	−81.7 (2)
C2—C21—C26—C25	−173.8 (3)	C4—C5—S1—C51	62.6 (2)
C24—C25—C26—C21	−0.7 (5)	C6—C5—S1—C51	−66.6 (2)
C56—C51—C52—C53	0.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.82	1.98	2.680 (4)	143
C26—H26···Cg1	0.93	2.95	3.698 (3)	139
C55—H55···Cg2^i	0.93	2.95	3.878 (3)	174

Symmetry code: (i) −x+1, y+3/2, −z+1/2.