Methyl 1-allyl-4-hy-droxy-2,2-dioxo-1H-2λ(6),1-benzo-thia-zine-3-carboxyl-ate.

There are two independent mol-ecules in the asymmetric unit of the title compound, C13H13NO5S, in both of which the ester substituent is nearly coplanar [C-C-C-O torsion angles = 2.7 (7) and -0.8 (7)°] with the planar fragment of the bicycle due to the formation of a strong O-H⋯O intra-molecular hydrogen bond. The vinyl group at the ring N atom is approximately orthogonal to the heterocyclic mean plane [C-N-C-C torsion angles = 103.1 (6) and 98.2 (5)°]. The refinement was performed on a two-component, non-merohedrally twinned crystal [population ratio = 0.483 (3):0.517 (3).

Related literature

For general properties of oxicams, see: Kleemann et al. (2008 ▶). For H⋯O contacts, see: Zefirov (1997 ▶) and for C—N bond lengths, see: Bürgi & Dunitz (1994 ▶).

Experimental

Crystal data

C13H13NO5S

M = 295.30

Monoclinic,

a = 17.8654 (12) Å

b = 6.9444 (5) Å

c = 21.1462 (16) Å

β = 90.122 (7)°

V = 2623.5 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.30 × 0.10 × 0.10 mm

Data collection

Agilent Xcalibur3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011 ▶) T min = 0.925, T max = 0.974

4647 measured reflections

4647 independent reflections

3728 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.218

S = 1.15

4647 reflections

366 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis CCD (Agilent, 2011 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Agilent, 2011 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813028572/bg2518sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028572/bg2518Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028572/bg2518Isup3.cml

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

C13H13NO5S	F(000) = 1232
Mr = 295.30	Dx = 1.495 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 17.8654 (12) Å	Cell parameters from 4369 reflections
b = 6.9444 (5) Å	θ = 2.9–32.0°
c = 21.1462 (16) Å	µ = 0.27 mm−1
β = 90.122 (7)°	T = 293 K
V = 2623.5 (3) Å3	Stick, colourless
Z = 8	0.30 × 0.10 × 0.10 mm

Agilent Xcalibur3 diffractometer	4647 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3728 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 16.1827 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −19→21
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2011)	k = −8→8
Tmin = 0.925, Tmax = 0.974	l = −25→25
4647 measured reflections

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)] = 0.069	Hydrogen site location: difference Fourier map
wR(F2) = 0.218	H-atom parameters constrained
S = 1.15	w = 1/[σ2(Fo2) + (0.1383P)2 + 0.312P] where P = (Fo2 + 2Fc2)/3
4647 reflections	(Δ/σ)max = 0.001
366 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.40 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
S1A	0.14036 (9)	0.3858 (2)	0.17531 (7)	0.0470 (4)
N1A	0.1098 (3)	0.2473 (7)	0.1181 (3)	0.0444 (12)
O1A	−0.0661 (3)	0.3675 (8)	0.2396 (3)	0.0712 (15)
H1OA	−0.0543	0.3505	0.2766	0.107*
O2A	0.0229 (3)	0.3701 (8)	0.3341 (2)	0.0733 (14)
O3A	0.1452 (3)	0.3964 (7)	0.3154 (2)	0.0612 (12)
O4A	0.1432 (3)	0.5799 (7)	0.1529 (2)	0.0626 (12)
O5A	0.2044 (3)	0.2977 (9)	0.1996 (2)	0.0737 (15)
C1A	0.0368 (3)	0.2867 (8)	0.0946 (3)	0.0446 (14)
C2A	0.0214 (4)	0.2520 (9)	0.0319 (3)	0.0545 (17)
H2A	0.0580	0.2029	0.0051	0.065*
C3A	−0.0493 (4)	0.2915 (11)	0.0099 (4)	0.068 (2)
H3A	−0.0600	0.2716	−0.0326	0.081*
C4A	−0.1044 (4)	0.3594 (10)	0.0488 (5)	0.072 (2)
H4A	−0.1515	0.3874	0.0323	0.087*
C5A	−0.0903 (4)	0.3864 (9)	0.1120 (4)	0.0579 (18)
H5A	−0.1282	0.4285	0.1387	0.070*
C6A	−0.0196 (4)	0.3509 (8)	0.1358 (3)	0.0455 (14)
C7A	−0.0051 (4)	0.3652 (8)	0.2037 (3)	0.0445 (15)
C8A	0.0646 (4)	0.3710 (8)	0.2297 (3)	0.0464 (15)
C9A	0.0758 (5)	0.3764 (9)	0.2972 (3)	0.0534 (17)
C10A	0.1605 (5)	0.3986 (11)	0.3825 (3)	0.072 (2)
H10A	0.2111	0.4399	0.3896	0.108*
H10B	0.1538	0.2715	0.3994	0.108*
H10C	0.1267	0.4859	0.4030	0.108*
C11A	0.1484 (5)	0.0682 (10)	0.1012 (3)	0.0633 (18)
H11A	0.1116	−0.0235	0.0861	0.076*
H11B	0.1709	0.0147	0.1392	0.076*
C12A	0.2079 (5)	0.0896 (18)	0.0522 (4)	0.089 (3)
H12A	0.2286	−0.0229	0.0360	0.106*
C13A	0.2336 (5)	0.255 (2)	0.0298 (4)	0.107 (4)
H13A	0.2144	0.3708	0.0446	0.128*
H13B	0.2709	0.2549	−0.0009	0.128*
S1B	0.36187 (9)	0.7281 (2)	0.43097 (7)	0.0483 (4)
N1B	0.3887 (3)	0.8759 (7)	0.3742 (2)	0.0462 (13)
O1B	0.5691 (2)	0.7495 (7)	0.4896 (2)	0.0588 (13)
H1OB	0.5583	0.7425	0.5272	0.088*
O2B	0.4815 (3)	0.7162 (7)	0.5863 (2)	0.0655 (13)
O3B	0.3585 (3)	0.7152 (7)	0.5704 (2)	0.0617 (12)
O4B	0.3600 (3)	0.5376 (6)	0.4066 (2)	0.0643 (13)
O5B	0.2942 (3)	0.8056 (8)	0.4570 (2)	0.0695 (14)
C1B	0.4624 (3)	0.8560 (8)	0.3489 (3)	0.0409 (14)
C2B	0.4758 (4)	0.9081 (9)	0.2867 (3)	0.0539 (17)
H2B	0.4370	0.9524	0.2613	0.065*
C3B	0.5496 (4)	0.8934 (9)	0.2621 (4)	0.0562 (17)
H3B	0.5592	0.9245	0.2201	0.067*
C4B	0.6055 (4)	0.8337 (9)	0.3004 (4)	0.0557 (17)
H4B	0.6539	0.8252	0.2844	0.067*
C5B	0.5925 (4)	0.7856 (9)	0.3619 (4)	0.0539 (17)
H5B	0.6322	0.7447	0.3870	0.065*
C6B	0.5194 (3)	0.7966 (7)	0.3885 (3)	0.0417 (13)
C7B	0.5071 (4)	0.7615 (8)	0.4556 (3)	0.0469 (15)
C8B	0.4367 (4)	0.7462 (8)	0.4823 (3)	0.0465 (15)
C9B	0.4276 (4)	0.7230 (8)	0.5511 (3)	0.0496 (16)
C10B	0.3435 (5)	0.7079 (11)	0.6370 (3)	0.068 (2)
H10D	0.3152	0.8194	0.6491	0.102*
H10E	0.3899	0.7054	0.6599	0.102*
H10F	0.3153	0.5938	0.6464	0.102*
C11B	0.3386 (4)	1.0290 (10)	0.3539 (3)	0.0561 (17)
H11C	0.3688	1.1344	0.3381	0.067*
H11D	0.3120	1.0760	0.3908	0.067*
C12B	0.2831 (4)	0.9795 (16)	0.3054 (4)	0.077 (3)
H12B	0.2564	1.0801	0.2872	0.093*
C13B	0.2678 (5)	0.799 (2)	0.2850 (4)	0.096 (3)
H13C	0.2934	0.6944	0.3021	0.116*
H13D	0.2317	0.7794	0.2539	0.116*

	U11	U22	U33	U12	U13	U23
S1A	0.0278 (7)	0.0627 (9)	0.0505 (7)	−0.0049 (7)	−0.0033 (8)	−0.0054 (7)
N1A	0.030 (2)	0.048 (3)	0.055 (3)	0.002 (2)	−0.001 (2)	−0.005 (2)
O1A	0.049 (3)	0.080 (4)	0.084 (3)	0.004 (2)	0.012 (3)	0.003 (3)
O2A	0.077 (4)	0.084 (4)	0.059 (3)	−0.007 (3)	0.018 (3)	−0.011 (2)
O3A	0.064 (3)	0.072 (3)	0.048 (2)	−0.007 (3)	−0.001 (3)	−0.005 (2)
O4A	0.057 (3)	0.062 (3)	0.068 (3)	−0.026 (2)	0.004 (3)	−0.004 (2)
O5A	0.035 (3)	0.123 (5)	0.063 (3)	0.007 (3)	−0.012 (2)	−0.011 (3)
C1A	0.037 (3)	0.038 (3)	0.059 (4)	−0.002 (3)	−0.009 (3)	0.003 (3)
C2A	0.048 (4)	0.052 (3)	0.063 (4)	−0.010 (3)	−0.021 (3)	0.001 (3)
C3A	0.064 (5)	0.059 (4)	0.080 (5)	−0.026 (4)	−0.029 (5)	0.013 (4)
C4A	0.046 (4)	0.064 (4)	0.107 (7)	−0.015 (4)	−0.036 (5)	0.029 (4)
C5A	0.034 (3)	0.045 (3)	0.094 (5)	0.005 (3)	−0.009 (4)	0.010 (3)
C6A	0.039 (3)	0.031 (3)	0.066 (4)	−0.008 (3)	−0.005 (3)	0.007 (3)
C7A	0.033 (3)	0.040 (3)	0.060 (4)	0.002 (2)	0.013 (3)	0.000 (3)
C8A	0.042 (4)	0.042 (3)	0.055 (3)	−0.003 (3)	0.009 (3)	−0.006 (3)
C9A	0.072 (5)	0.040 (3)	0.048 (3)	−0.003 (3)	0.011 (4)	−0.002 (3)
C10A	0.107 (7)	0.056 (4)	0.053 (4)	−0.004 (4)	−0.015 (4)	−0.009 (3)
C11A	0.065 (5)	0.054 (4)	0.071 (4)	0.011 (4)	−0.009 (4)	−0.011 (3)
C12A	0.056 (5)	0.149 (9)	0.061 (5)	0.057 (6)	−0.011 (4)	−0.035 (5)
C13A	0.043 (5)	0.218 (13)	0.058 (5)	−0.023 (7)	−0.007 (4)	0.019 (7)
S1B	0.0336 (8)	0.0578 (9)	0.0535 (8)	−0.0016 (8)	−0.0105 (8)	0.0126 (7)
N1B	0.036 (3)	0.049 (3)	0.053 (3)	0.006 (2)	0.000 (2)	0.012 (2)
O1B	0.032 (2)	0.074 (3)	0.071 (3)	0.003 (2)	−0.022 (2)	0.003 (3)
O2B	0.060 (3)	0.076 (3)	0.061 (3)	0.012 (3)	−0.027 (3)	−0.005 (2)
O3B	0.057 (3)	0.079 (3)	0.049 (2)	−0.010 (3)	0.001 (3)	0.000 (2)
O4B	0.064 (3)	0.051 (2)	0.078 (3)	−0.027 (2)	−0.027 (3)	0.013 (2)
O5B	0.040 (3)	0.099 (4)	0.070 (3)	0.006 (2)	0.001 (2)	0.023 (3)
C1B	0.032 (3)	0.035 (3)	0.056 (3)	0.003 (2)	−0.007 (3)	0.004 (3)
C2B	0.057 (4)	0.041 (3)	0.063 (4)	0.007 (3)	−0.006 (3)	0.005 (3)
C3B	0.055 (4)	0.042 (3)	0.071 (4)	−0.006 (3)	0.014 (4)	0.002 (3)
C4B	0.031 (3)	0.048 (4)	0.088 (5)	−0.001 (3)	0.012 (3)	−0.009 (4)
C5B	0.038 (4)	0.037 (3)	0.086 (5)	0.010 (3)	−0.009 (4)	−0.007 (3)
C6B	0.027 (3)	0.030 (3)	0.069 (4)	−0.002 (2)	−0.003 (3)	−0.005 (3)
C7B	0.043 (4)	0.036 (3)	0.062 (4)	0.005 (3)	−0.014 (3)	−0.004 (3)
C8B	0.040 (4)	0.037 (3)	0.063 (4)	−0.001 (2)	−0.011 (3)	0.002 (3)
C9B	0.057 (4)	0.039 (3)	0.053 (3)	0.004 (3)	−0.008 (3)	−0.005 (3)
C10B	0.091 (6)	0.068 (4)	0.046 (3)	0.002 (4)	−0.004 (4)	−0.004 (3)
C11B	0.044 (4)	0.060 (4)	0.065 (4)	0.017 (3)	0.006 (3)	0.014 (3)
C12B	0.039 (4)	0.130 (8)	0.063 (4)	0.017 (4)	−0.002 (3)	0.041 (5)
C13B	0.074 (6)	0.166 (11)	0.049 (4)	−0.024 (6)	−0.013 (4)	0.008 (5)

S1A—O5A	1.394 (5)	S1B—O4B	1.420 (5)
S1A—O4A	1.430 (5)	S1B—O5B	1.435 (6)
S1A—N1A	1.638 (5)	S1B—N1B	1.651 (5)
S1A—C8A	1.782 (7)	S1B—C8B	1.724 (6)
N1A—C1A	1.421 (7)	N1B—C1B	1.429 (8)
N1A—C11A	1.467 (8)	N1B—C11B	1.454 (8)
O1A—C7A	1.330 (8)	O1B—C7B	1.321 (7)
O1A—H1OA	0.8200	O1B—H1OB	0.8200
O2A—C9A	1.226 (9)	O2B—C9B	1.217 (8)
O3A—C9A	1.305 (9)	O3B—C9B	1.303 (8)
O3A—C10A	1.445 (8)	O3B—C10B	1.434 (8)
C1A—C2A	1.374 (9)	C1B—C6B	1.382 (8)
C1A—C6A	1.406 (9)	C1B—C2B	1.385 (9)
C2A—C3A	1.373 (10)	C2B—C3B	1.422 (10)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—C4A	1.367 (12)	C3B—C4B	1.349 (10)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—C5A	1.373 (12)	C4B—C5B	1.364 (10)
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.381 (9)	C5B—C6B	1.426 (9)
C5A—H5A	0.9300	C5B—H5B	0.9300
C6A—C7A	1.464 (9)	C6B—C7B	1.456 (9)
C7A—C8A	1.359 (9)	C7B—C8B	1.385 (10)
C8A—C9A	1.442 (9)	C8B—C9B	1.472 (10)
C10A—H10A	0.9600	C10B—H10D	0.9600
C10A—H10B	0.9600	C10B—H10E	0.9600
C10A—H10C	0.9600	C10B—H10F	0.9600
C11A—C12A	1.493 (13)	C11B—C12B	1.465 (11)
C11A—H11A	0.9700	C11B—H11C	0.9700
C11A—H11B	0.9700	C11B—H11D	0.9700
C12A—C13A	1.325 (16)	C12B—C13B	1.354 (15)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—H13A	0.9300	C13B—H13C	0.9300
C13A—H13B	0.9300	C13B—H13D	0.9300
O5A—S1A—O4A	120.4 (3)	O4B—S1B—O5B	118.0 (3)
O5A—S1A—N1A	106.6 (3)	O4B—S1B—N1B	108.8 (3)
O4A—S1A—N1A	108.7 (3)	O5B—S1B—N1B	106.9 (3)
O5A—S1A—C8A	111.2 (3)	O4B—S1B—C8B	108.3 (3)
O4A—S1A—C8A	107.3 (3)	O5B—S1B—C8B	112.6 (3)
N1A—S1A—C8A	101.0 (3)	N1B—S1B—C8B	100.8 (3)
C1A—N1A—C11A	120.7 (5)	C1B—N1B—C11B	121.8 (5)
C1A—N1A—S1A	116.7 (4)	C1B—N1B—S1B	118.8 (4)
C11A—N1A—S1A	121.4 (4)	C11B—N1B—S1B	119.3 (4)
C7A—O1A—H1OA	109.5	C7B—O1B—H1OB	109.5
C9A—O3A—C10A	117.9 (6)	C9B—O3B—C10B	119.3 (6)
C2A—C1A—C6A	120.7 (6)	C6B—C1B—C2B	121.6 (6)
C2A—C1A—N1A	119.0 (6)	C6B—C1B—N1B	118.7 (5)
C6A—C1A—N1A	120.2 (6)	C2B—C1B—N1B	119.5 (5)
C3A—C2A—C1A	118.3 (8)	C1B—C2B—C3B	119.5 (6)
C3A—C2A—H2A	120.9	C1B—C2B—H2B	120.3
C1A—C2A—H2A	120.9	C3B—C2B—H2B	120.3
C4A—C3A—C2A	121.9 (8)	C4B—C3B—C2B	119.3 (7)
C4A—C3A—H3A	119.0	C4B—C3B—H3B	120.4
C2A—C3A—H3A	119.0	C2B—C3B—H3B	120.4
C3A—C4A—C5A	120.1 (7)	C3B—C4B—C5B	121.3 (6)
C3A—C4A—H4A	120.0	C3B—C4B—H4B	119.4
C5A—C4A—H4A	120.0	C5B—C4B—H4B	119.4
C4A—C5A—C6A	119.7 (8)	C4B—C5B—C6B	121.5 (6)
C4A—C5A—H5A	120.1	C4B—C5B—H5B	119.2
C6A—C5A—H5A	120.1	C6B—C5B—H5B	119.2
C5A—C6A—C1A	119.2 (6)	C1B—C6B—C5B	116.8 (6)
C5A—C6A—C7A	120.4 (7)	C1B—C6B—C7B	121.9 (6)
C1A—C6A—C7A	120.2 (6)	C5B—C6B—C7B	121.1 (6)
O1A—C7A—C8A	121.4 (6)	O1B—C7B—C8B	122.3 (6)
O1A—C7A—C6A	114.6 (6)	O1B—C7B—C6B	114.4 (6)
C8A—C7A—C6A	124.0 (6)	C8B—C7B—C6B	123.3 (6)
C7A—C8A—C9A	121.7 (7)	C7B—C8B—C9B	120.8 (6)
C7A—C8A—S1A	115.9 (5)	C7B—C8B—S1B	116.9 (5)
C9A—C8A—S1A	122.3 (6)	C9B—C8B—S1B	121.8 (5)
O2A—C9A—O3A	123.3 (6)	O2B—C9B—O3B	123.7 (6)
O2A—C9A—C8A	121.6 (7)	O2B—C9B—C8B	121.4 (7)
O3A—C9A—C8A	115.1 (6)	O3B—C9B—C8B	114.9 (6)
O3A—C10A—H10A	109.5	O3B—C10B—H10D	109.5
O3A—C10A—H10B	109.5	O3B—C10B—H10E	109.5
H10A—C10A—H10B	109.5	H10D—C10B—H10E	109.5
O3A—C10A—H10C	109.5	O3B—C10B—H10F	109.5
H10A—C10A—H10C	109.5	H10D—C10B—H10F	109.5
H10B—C10A—H10C	109.5	H10E—C10B—H10F	109.5
N1A—C11A—C12A	114.9 (7)	N1B—C11B—C12B	116.7 (7)
N1A—C11A—H11A	108.6	N1B—C11B—H11C	108.1
C12A—C11A—H11A	108.6	C12B—C11B—H11C	108.1
N1A—C11A—H11B	108.6	N1B—C11B—H11D	108.1
C12A—C11A—H11B	108.6	C12B—C11B—H11D	108.1
H11A—C11A—H11B	107.5	H11C—C11B—H11D	107.3
C13A—C12A—C11A	125.7 (9)	C13B—C12B—C11B	125.2 (8)
C13A—C12A—H12A	117.2	C13B—C12B—H12B	117.4
C11A—C12A—H12A	117.2	C11B—C12B—H12B	117.4
C12A—C13A—H13A	120.0	C12B—C13B—H13C	120.0
C12A—C13A—H13B	120.0	C12B—C13B—H13D	120.0
H13A—C13A—H13B	120.0	H13C—C13B—H13D	120.0
O5A—S1A—N1A—C1A	167.7 (5)	O4B—S1B—N1B—C1B	−64.2 (5)
O4A—S1A—N1A—C1A	−61.2 (5)	O5B—S1B—N1B—C1B	167.3 (5)
C8A—S1A—N1A—C1A	51.4 (5)	C8B—S1B—N1B—C1B	49.4 (5)
O5A—S1A—N1A—C11A	0.2 (6)	O4B—S1B—N1B—C11B	119.2 (5)
O4A—S1A—N1A—C11A	131.4 (5)	O5B—S1B—N1B—C11B	−9.3 (6)
C8A—S1A—N1A—C11A	−116.0 (5)	C8B—S1B—N1B—C11B	−127.1 (5)
C11A—N1A—C1A—C2A	−44.4 (8)	C11B—N1B—C1B—C6B	143.2 (6)
S1A—N1A—C1A—C2A	148.1 (5)	S1B—N1B—C1B—C6B	−33.2 (7)
C11A—N1A—C1A—C6A	132.4 (6)	C11B—N1B—C1B—C2B	−32.6 (9)
S1A—N1A—C1A—C6A	−35.1 (7)	S1B—N1B—C1B—C2B	150.9 (5)
C6A—C1A—C2A—C3A	3.5 (9)	C6B—C1B—C2B—C3B	2.5 (9)
N1A—C1A—C2A—C3A	−179.7 (6)	N1B—C1B—C2B—C3B	178.2 (5)
C1A—C2A—C3A—C4A	−1.6 (10)	C1B—C2B—C3B—C4B	−1.8 (9)
C2A—C3A—C4A—C5A	−1.3 (11)	C2B—C3B—C4B—C5B	0.6 (9)
C3A—C4A—C5A—C6A	2.2 (10)	C3B—C4B—C5B—C6B	−0.2 (9)
C4A—C5A—C6A—C1A	−0.3 (9)	C2B—C1B—C6B—C5B	−2.0 (8)
C4A—C5A—C6A—C7A	−175.5 (6)	N1B—C1B—C6B—C5B	−177.7 (5)
C2A—C1A—C6A—C5A	−2.6 (9)	C2B—C1B—C6B—C7B	173.3 (6)
N1A—C1A—C6A—C5A	−179.4 (5)	N1B—C1B—C6B—C7B	−2.5 (8)
C2A—C1A—C6A—C7A	172.6 (5)	C4B—C5B—C6B—C1B	0.8 (8)
N1A—C1A—C6A—C7A	−4.1 (8)	C4B—C5B—C6B—C7B	−174.5 (6)
C5A—C6A—C7A—O1A	15.4 (8)	C1B—C6B—C7B—O1B	−165.1 (5)
C1A—C6A—C7A—O1A	−159.8 (5)	C5B—C6B—C7B—O1B	9.9 (8)
C5A—C6A—C7A—C8A	−166.3 (6)	C1B—C6B—C7B—C8B	13.5 (9)
C1A—C6A—C7A—C8A	18.6 (9)	C5B—C6B—C7B—C8B	−171.5 (5)
O1A—C7A—C8A—C9A	1.1 (9)	O1B—C7B—C8B—C9B	2.4 (9)
C6A—C7A—C8A—C9A	−177.1 (5)	C6B—C7B—C8B—C9B	−176.1 (5)
O1A—C7A—C8A—S1A	−175.3 (5)	O1B—C7B—C8B—S1B	−170.5 (4)
C6A—C7A—C8A—S1A	6.4 (8)	C6B—C7B—C8B—S1B	11.1 (8)
O5A—S1A—C8A—C7A	−150.2 (5)	O4B—S1B—C8B—C7B	76.5 (5)
O4A—S1A—C8A—C7A	76.4 (5)	O5B—S1B—C8B—C7B	−151.2 (4)
N1A—S1A—C8A—C7A	−37.3 (5)	N1B—S1B—C8B—C7B	−37.6 (5)
O5A—S1A—C8A—C9A	33.4 (6)	O4B—S1B—C8B—C9B	−96.3 (5)
O4A—S1A—C8A—C9A	−100.1 (5)	O5B—S1B—C8B—C9B	36.0 (6)
N1A—S1A—C8A—C9A	146.2 (5)	N1B—S1B—C8B—C9B	149.6 (5)
C10A—O3A—C9A—O2A	4.1 (9)	C10B—O3B—C9B—O2B	3.3 (9)
C10A—O3A—C9A—C8A	−178.7 (5)	C10B—O3B—C9B—C8B	−175.2 (5)
C7A—C8A—C9A—O2A	2.2 (9)	C7B—C8B—C9B—O2B	−0.2 (9)
S1A—C8A—C9A—O2A	178.5 (5)	S1B—C8B—C9B—O2B	172.3 (5)
C7A—C8A—C9A—O3A	−175.0 (5)	C7B—C8B—C9B—O3B	178.3 (5)
S1A—C8A—C9A—O3A	1.2 (8)	S1B—C8B—C9B—O3B	−9.2 (8)
C1A—N1A—C11A—C12A	103.1 (7)	C1B—N1B—C11B—C12B	97.5 (7)
S1A—N1A—C11A—C12A	−89.9 (7)	S1B—N1B—C11B—C12B	−86.1 (7)
N1A—C11A—C12A—C13A	8.8 (11)	N1B—C11B—C12B—C13B	10.2 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1OA···O2A	0.82	1.84	2.553 (8)	144
O1B—H1OB···O2B	0.82	1.87	2.588 (8)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1OA⋯O2A	0.82	1.84	2.553 (8)	144
O1B—H1OB⋯O2B	0.82	1.87	2.588 (8)	146