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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Methyl 1-allyl-4-hy­dr­oxy-2,2-dioxo-1H-2λ6,1-benzo­thia­zine-3-carboxyl­ate

aSTC "Institute for Single Crystals", National Academy of Sciences of Ukraine, 60 Lenina ave., Kharkiv 61001, Ukraine, and bNational University of Pharmacy, 4 Blyukhera St, Kharkiv 61168, Ukraine
*Correspondence e-mail: sveta@xray.isc.kharkov.com

(Received 12 September 2013; accepted 17 October 2013; online 23 October 2013)

There are two independent mol­ecules 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 intra­molecular 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[Kleemann, A., Engel, J., Kutscher, B. & Reihert, D. (2008). Pharmaceutical Substances: Syntheses, Patents, Applications of the most relevant APIs, 5th ed. Stuttgart: Thieme.]). For H⋯O contacts, see: Zefirov (1997[Zefirov, Y. V. (1997). Kristallografiya, 42, 936-958.]) and for C—N bond lengths, see: Bürgi & Dunitz (1994[Bürgi, H.-B. & Dunitz, J. D. (1994). Structure Correlation, Vol. 2, pp. 767-784. Weinheim: VCH.]).

[Scheme 1]

Experimental

Crystal data
  • C13H13NO5S

  • Mr = 295.30

  • Monoclinic, P 21 /c

  • 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[Agilent (2011). CrysAlis CCD and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.925, Tmax = 0.974

  • 4647 measured reflections

  • 4647 independent reflections

  • 3728 reflections with I > 2σ(I)

Refinement
  • R[F2 > 2σ(F2)] = 0.069

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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

Data collection: CrysAlis CCD (Agilent, 2011[Agilent (2011). CrysAlis CCD and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Agilent, 2011[Agilent (2011). CrysAlis CCD and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Oxicams are in integral part of the range of modern non-steroidal anti-inflammatory drugs (Kleemann et al., 2008). We have carried out the synthesis and studied the peculiarities of the spatial structure of methyl 4-hydroxy-1-methyl-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate (I) being of interest as the initial product for obtaining 4-hydroxy-2,2-dioxo-1H- 2λ6,1-benzothiazine-3-carboxamides. By now these compounds remain absolutely unstudied though they are isomers of oxicams and differ from them only by the reverse mutual arrangement of nitrogen and sulfur atoms in the thiazine cycle. Two molecules (IA and IB) are observed in asymmetric part of crystal unit cell. The dihydrothiazine heterocycle adopts an intermediate between twist-boat and sofa conformation (the puckering parameters [1] are: S=0.64, Θ=55.8°, Ψ=22.9° for IA and S=0.61, Θ=50.2°, Ψ=21.1° for IB). Deviations of the S1 and C8 atoms from the mean plane of the remaining atoms of this ring are 0.91 Å and 0.29 Å, respectivey, in IA and -0.84 Å and -0.23 Å, in IB. The formation of the strong O1—H···O2 hydrogen bond (Table 1) results in coplanarity of the ester substituent to the C7—C8 endocyclic double bond (the C7—C8—C9—O2 torsion angle is 2.7 (7)° in IA and -0.8 (7)° in IB). The vinyl fragment is orthogonal to the hetetocyclic plane and is coplanar to the N1—C11 bond (the C1—N1—C11—C12 and N1—C11—C12—C13 torsion angles are 103.1 (6)° IA 98.2 (5)° IB and 9.3 (9)° IA 8.5 (9)%A IB, respectively). The repulsion between allyl substituent and atoms of the bicyclic fragment [the H2···C11 distance is 2.76Å IA 2.70Å IB, H11a···C2 2.76Å IA 2.71° IB, H11b···O5 2.41Å IA 2.38Å IB as compared to the van der Waals radii sum 2.87 Å for H···C contact and 2.46 Å for H···O (Zefirov, 1997)] results in elongation of the C1—N1 bond up to 1.416 (6) Å in IA and 1.414 (6) Å in IB while its mean value is 1.371 Å (Bürgi & Dunitz, 1994).

Related literature top

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 top

Triethylamine (1.54 ml, 11 mmol) was added to the solution of methyl N-allylanthranilate (1.91 g, 10 mmol) in CH2Cl2 (20 ml). Chlorosulfonyl acetic acid ethyl ester (2.05 g, 11 mol) was then added dropwise with cooling and stirring and left at the room temperature for 5 h. The reaction mixture was diluted with a cold water and vigorously stirred. The organic layer was separated, dried over CaCl2, and the solvent was distilled off (finally under reduced pressure). The residue was treated with the solution of sodium methylate (prepared from metallic sodium (0.69 g, 30 mmol) and absolute MeOH (15 ml)), taken fo reflux, and then left for 10–12 h at the room temperature. The reaction mixture was diluted with cold water and acidified with 1 N HCl to pH 3. The precipitate was filtered, washed with water, and dried. Yield 2.39 g (81%). M.p. 114–116%A C (MeOH).

Refinement top

The refinement was performed on a two-component, non-merohedral twinned crystal (Refined populations: 0.483 (3),0.517 (3) ). All hydrogen atoms were located from electron density difference maps and were refined in the riding motion approximation with Uiso constrained to be 1.5 times Ueq of the carrier atom for the methyl and hydroxyl groups and 1.2 times Ueq of the carrier atom for the other atoms.

Computing details top

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

Figures top
[Figure 1] Fig. 1. View of the title compound with atomic membering. All atoms are shown with displacement ellipsoids drawn at the 50% probability level.
Methyl 1-allyl-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate top
Crystal data top
C13H13NO5SF(000) = 1232
Mr = 295.30Dx = 1.495 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 17.8654 (12) ÅCell parameters from 4369 reflections
b = 6.9444 (5) Åθ = 2.9–32.0°
c = 21.1462 (16) ŵ = 0.27 mm1
β = 90.122 (7)°T = 293 K
V = 2623.5 (3) Å3Stick, colourless
Z = 80.30 × 0.10 × 0.10 mm
Data collection top
Agilent Xcalibur3
diffractometer
4647 independent reflections
Radiation source: Enhance (Mo) X-ray Source3728 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
Detector resolution: 16.1827 pixels mm-1θmax = 25.0°, θmin = 3.0°
ω scansh = 1921
Absorption correction: multi-scan
(CrysAlis RED; Agilent, 2011)
k = 88
Tmin = 0.925, Tmax = 0.974l = 2525
4647 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.069Hydrogen site location: difference Fourier map
wR(F2) = 0.218H-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 parametersΔρmax = 0.41 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
C13H13NO5SV = 2623.5 (3) Å3
Mr = 295.30Z = 8
Monoclinic, P21/cMo Kα radiation
a = 17.8654 (12) ŵ = 0.27 mm1
b = 6.9444 (5) ÅT = 293 K
c = 21.1462 (16) Å0.30 × 0.10 × 0.10 mm
β = 90.122 (7)°
Data collection top
Agilent Xcalibur3
diffractometer
4647 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Agilent, 2011)
3728 reflections with I > 2σ(I)
Tmin = 0.925, Tmax = 0.974Rint = 0.000
4647 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0690 restraints
wR(F2) = 0.218H-atom parameters constrained
S = 1.15Δρmax = 0.41 e Å3
4647 reflectionsΔρmin = 0.40 e Å3
366 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
S1A0.14036 (9)0.3858 (2)0.17531 (7)0.0470 (4)
N1A0.1098 (3)0.2473 (7)0.1181 (3)0.0444 (12)
O1A0.0661 (3)0.3675 (8)0.2396 (3)0.0712 (15)
H1OA0.05430.35050.27660.107*
O2A0.0229 (3)0.3701 (8)0.3341 (2)0.0733 (14)
O3A0.1452 (3)0.3964 (7)0.3154 (2)0.0612 (12)
O4A0.1432 (3)0.5799 (7)0.1529 (2)0.0626 (12)
O5A0.2044 (3)0.2977 (9)0.1996 (2)0.0737 (15)
C1A0.0368 (3)0.2867 (8)0.0946 (3)0.0446 (14)
C2A0.0214 (4)0.2520 (9)0.0319 (3)0.0545 (17)
H2A0.05800.20290.00510.065*
C3A0.0493 (4)0.2915 (11)0.0099 (4)0.068 (2)
H3A0.06000.27160.03260.081*
C4A0.1044 (4)0.3594 (10)0.0488 (5)0.072 (2)
H4A0.15150.38740.03230.087*
C5A0.0903 (4)0.3864 (9)0.1120 (4)0.0579 (18)
H5A0.12820.42850.13870.070*
C6A0.0196 (4)0.3509 (8)0.1358 (3)0.0455 (14)
C7A0.0051 (4)0.3652 (8)0.2037 (3)0.0445 (15)
C8A0.0646 (4)0.3710 (8)0.2297 (3)0.0464 (15)
C9A0.0758 (5)0.3764 (9)0.2972 (3)0.0534 (17)
C10A0.1605 (5)0.3986 (11)0.3825 (3)0.072 (2)
H10A0.21110.43990.38960.108*
H10B0.15380.27150.39940.108*
H10C0.12670.48590.40300.108*
C11A0.1484 (5)0.0682 (10)0.1012 (3)0.0633 (18)
H11A0.11160.02350.08610.076*
H11B0.17090.01470.13920.076*
C12A0.2079 (5)0.0896 (18)0.0522 (4)0.089 (3)
H12A0.22860.02290.03600.106*
C13A0.2336 (5)0.255 (2)0.0298 (4)0.107 (4)
H13A0.21440.37080.04460.128*
H13B0.27090.25490.00090.128*
S1B0.36187 (9)0.7281 (2)0.43097 (7)0.0483 (4)
N1B0.3887 (3)0.8759 (7)0.3742 (2)0.0462 (13)
O1B0.5691 (2)0.7495 (7)0.4896 (2)0.0588 (13)
H1OB0.55830.74250.52720.088*
O2B0.4815 (3)0.7162 (7)0.5863 (2)0.0655 (13)
O3B0.3585 (3)0.7152 (7)0.5704 (2)0.0617 (12)
O4B0.3600 (3)0.5376 (6)0.4066 (2)0.0643 (13)
O5B0.2942 (3)0.8056 (8)0.4570 (2)0.0695 (14)
C1B0.4624 (3)0.8560 (8)0.3489 (3)0.0409 (14)
C2B0.4758 (4)0.9081 (9)0.2867 (3)0.0539 (17)
H2B0.43700.95240.26130.065*
C3B0.5496 (4)0.8934 (9)0.2621 (4)0.0562 (17)
H3B0.55920.92450.22010.067*
C4B0.6055 (4)0.8337 (9)0.3004 (4)0.0557 (17)
H4B0.65390.82520.28440.067*
C5B0.5925 (4)0.7856 (9)0.3619 (4)0.0539 (17)
H5B0.63220.74470.38700.065*
C6B0.5194 (3)0.7966 (7)0.3885 (3)0.0417 (13)
C7B0.5071 (4)0.7615 (8)0.4556 (3)0.0469 (15)
C8B0.4367 (4)0.7462 (8)0.4823 (3)0.0465 (15)
C9B0.4276 (4)0.7230 (8)0.5511 (3)0.0496 (16)
C10B0.3435 (5)0.7079 (11)0.6370 (3)0.068 (2)
H10D0.31520.81940.64910.102*
H10E0.38990.70540.65990.102*
H10F0.31530.59380.64640.102*
C11B0.3386 (4)1.0290 (10)0.3539 (3)0.0561 (17)
H11C0.36881.13440.33810.067*
H11D0.31201.07600.39080.067*
C12B0.2831 (4)0.9795 (16)0.3054 (4)0.077 (3)
H12B0.25641.08010.28720.093*
C13B0.2678 (5)0.799 (2)0.2850 (4)0.096 (3)
H13C0.29340.69440.30210.116*
H13D0.23170.77940.25390.116*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0278 (7)0.0627 (9)0.0505 (7)0.0049 (7)0.0033 (8)0.0054 (7)
N1A0.030 (2)0.048 (3)0.055 (3)0.002 (2)0.001 (2)0.005 (2)
O1A0.049 (3)0.080 (4)0.084 (3)0.004 (2)0.012 (3)0.003 (3)
O2A0.077 (4)0.084 (4)0.059 (3)0.007 (3)0.018 (3)0.011 (2)
O3A0.064 (3)0.072 (3)0.048 (2)0.007 (3)0.001 (3)0.005 (2)
O4A0.057 (3)0.062 (3)0.068 (3)0.026 (2)0.004 (3)0.004 (2)
O5A0.035 (3)0.123 (5)0.063 (3)0.007 (3)0.012 (2)0.011 (3)
C1A0.037 (3)0.038 (3)0.059 (4)0.002 (3)0.009 (3)0.003 (3)
C2A0.048 (4)0.052 (3)0.063 (4)0.010 (3)0.021 (3)0.001 (3)
C3A0.064 (5)0.059 (4)0.080 (5)0.026 (4)0.029 (5)0.013 (4)
C4A0.046 (4)0.064 (4)0.107 (7)0.015 (4)0.036 (5)0.029 (4)
C5A0.034 (3)0.045 (3)0.094 (5)0.005 (3)0.009 (4)0.010 (3)
C6A0.039 (3)0.031 (3)0.066 (4)0.008 (3)0.005 (3)0.007 (3)
C7A0.033 (3)0.040 (3)0.060 (4)0.002 (2)0.013 (3)0.000 (3)
C8A0.042 (4)0.042 (3)0.055 (3)0.003 (3)0.009 (3)0.006 (3)
C9A0.072 (5)0.040 (3)0.048 (3)0.003 (3)0.011 (4)0.002 (3)
C10A0.107 (7)0.056 (4)0.053 (4)0.004 (4)0.015 (4)0.009 (3)
C11A0.065 (5)0.054 (4)0.071 (4)0.011 (4)0.009 (4)0.011 (3)
C12A0.056 (5)0.149 (9)0.061 (5)0.057 (6)0.011 (4)0.035 (5)
C13A0.043 (5)0.218 (13)0.058 (5)0.023 (7)0.007 (4)0.019 (7)
S1B0.0336 (8)0.0578 (9)0.0535 (8)0.0016 (8)0.0105 (8)0.0126 (7)
N1B0.036 (3)0.049 (3)0.053 (3)0.006 (2)0.000 (2)0.012 (2)
O1B0.032 (2)0.074 (3)0.071 (3)0.003 (2)0.022 (2)0.003 (3)
O2B0.060 (3)0.076 (3)0.061 (3)0.012 (3)0.027 (3)0.005 (2)
O3B0.057 (3)0.079 (3)0.049 (2)0.010 (3)0.001 (3)0.000 (2)
O4B0.064 (3)0.051 (2)0.078 (3)0.027 (2)0.027 (3)0.013 (2)
O5B0.040 (3)0.099 (4)0.070 (3)0.006 (2)0.001 (2)0.023 (3)
C1B0.032 (3)0.035 (3)0.056 (3)0.003 (2)0.007 (3)0.004 (3)
C2B0.057 (4)0.041 (3)0.063 (4)0.007 (3)0.006 (3)0.005 (3)
C3B0.055 (4)0.042 (3)0.071 (4)0.006 (3)0.014 (4)0.002 (3)
C4B0.031 (3)0.048 (4)0.088 (5)0.001 (3)0.012 (3)0.009 (4)
C5B0.038 (4)0.037 (3)0.086 (5)0.010 (3)0.009 (4)0.007 (3)
C6B0.027 (3)0.030 (3)0.069 (4)0.002 (2)0.003 (3)0.005 (3)
C7B0.043 (4)0.036 (3)0.062 (4)0.005 (3)0.014 (3)0.004 (3)
C8B0.040 (4)0.037 (3)0.063 (4)0.001 (2)0.011 (3)0.002 (3)
C9B0.057 (4)0.039 (3)0.053 (3)0.004 (3)0.008 (3)0.005 (3)
C10B0.091 (6)0.068 (4)0.046 (3)0.002 (4)0.004 (4)0.004 (3)
C11B0.044 (4)0.060 (4)0.065 (4)0.017 (3)0.006 (3)0.014 (3)
C12B0.039 (4)0.130 (8)0.063 (4)0.017 (4)0.002 (3)0.041 (5)
C13B0.074 (6)0.166 (11)0.049 (4)0.024 (6)0.013 (4)0.008 (5)
Geometric parameters (Å, º) top
S1A—O5A1.394 (5)S1B—O4B1.420 (5)
S1A—O4A1.430 (5)S1B—O5B1.435 (6)
S1A—N1A1.638 (5)S1B—N1B1.651 (5)
S1A—C8A1.782 (7)S1B—C8B1.724 (6)
N1A—C1A1.421 (7)N1B—C1B1.429 (8)
N1A—C11A1.467 (8)N1B—C11B1.454 (8)
O1A—C7A1.330 (8)O1B—C7B1.321 (7)
O1A—H1OA0.8200O1B—H1OB0.8200
O2A—C9A1.226 (9)O2B—C9B1.217 (8)
O3A—C9A1.305 (9)O3B—C9B1.303 (8)
O3A—C10A1.445 (8)O3B—C10B1.434 (8)
C1A—C2A1.374 (9)C1B—C6B1.382 (8)
C1A—C6A1.406 (9)C1B—C2B1.385 (9)
C2A—C3A1.373 (10)C2B—C3B1.422 (10)
C2A—H2A0.9300C2B—H2B0.9300
C3A—C4A1.367 (12)C3B—C4B1.349 (10)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.373 (12)C4B—C5B1.364 (10)
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.381 (9)C5B—C6B1.426 (9)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C7A1.464 (9)C6B—C7B1.456 (9)
C7A—C8A1.359 (9)C7B—C8B1.385 (10)
C8A—C9A1.442 (9)C8B—C9B1.472 (10)
C10A—H10A0.9600C10B—H10D0.9600
C10A—H10B0.9600C10B—H10E0.9600
C10A—H10C0.9600C10B—H10F0.9600
C11A—C12A1.493 (13)C11B—C12B1.465 (11)
C11A—H11A0.9700C11B—H11C0.9700
C11A—H11B0.9700C11B—H11D0.9700
C12A—C13A1.325 (16)C12B—C13B1.354 (15)
C12A—H12A0.9300C12B—H12B0.9300
C13A—H13A0.9300C13B—H13C0.9300
C13A—H13B0.9300C13B—H13D0.9300
O5A—S1A—O4A120.4 (3)O4B—S1B—O5B118.0 (3)
O5A—S1A—N1A106.6 (3)O4B—S1B—N1B108.8 (3)
O4A—S1A—N1A108.7 (3)O5B—S1B—N1B106.9 (3)
O5A—S1A—C8A111.2 (3)O4B—S1B—C8B108.3 (3)
O4A—S1A—C8A107.3 (3)O5B—S1B—C8B112.6 (3)
N1A—S1A—C8A101.0 (3)N1B—S1B—C8B100.8 (3)
C1A—N1A—C11A120.7 (5)C1B—N1B—C11B121.8 (5)
C1A—N1A—S1A116.7 (4)C1B—N1B—S1B118.8 (4)
C11A—N1A—S1A121.4 (4)C11B—N1B—S1B119.3 (4)
C7A—O1A—H1OA109.5C7B—O1B—H1OB109.5
C9A—O3A—C10A117.9 (6)C9B—O3B—C10B119.3 (6)
C2A—C1A—C6A120.7 (6)C6B—C1B—C2B121.6 (6)
C2A—C1A—N1A119.0 (6)C6B—C1B—N1B118.7 (5)
C6A—C1A—N1A120.2 (6)C2B—C1B—N1B119.5 (5)
C3A—C2A—C1A118.3 (8)C1B—C2B—C3B119.5 (6)
C3A—C2A—H2A120.9C1B—C2B—H2B120.3
C1A—C2A—H2A120.9C3B—C2B—H2B120.3
C4A—C3A—C2A121.9 (8)C4B—C3B—C2B119.3 (7)
C4A—C3A—H3A119.0C4B—C3B—H3B120.4
C2A—C3A—H3A119.0C2B—C3B—H3B120.4
C3A—C4A—C5A120.1 (7)C3B—C4B—C5B121.3 (6)
C3A—C4A—H4A120.0C3B—C4B—H4B119.4
C5A—C4A—H4A120.0C5B—C4B—H4B119.4
C4A—C5A—C6A119.7 (8)C4B—C5B—C6B121.5 (6)
C4A—C5A—H5A120.1C4B—C5B—H5B119.2
C6A—C5A—H5A120.1C6B—C5B—H5B119.2
C5A—C6A—C1A119.2 (6)C1B—C6B—C5B116.8 (6)
C5A—C6A—C7A120.4 (7)C1B—C6B—C7B121.9 (6)
C1A—C6A—C7A120.2 (6)C5B—C6B—C7B121.1 (6)
O1A—C7A—C8A121.4 (6)O1B—C7B—C8B122.3 (6)
O1A—C7A—C6A114.6 (6)O1B—C7B—C6B114.4 (6)
C8A—C7A—C6A124.0 (6)C8B—C7B—C6B123.3 (6)
C7A—C8A—C9A121.7 (7)C7B—C8B—C9B120.8 (6)
C7A—C8A—S1A115.9 (5)C7B—C8B—S1B116.9 (5)
C9A—C8A—S1A122.3 (6)C9B—C8B—S1B121.8 (5)
O2A—C9A—O3A123.3 (6)O2B—C9B—O3B123.7 (6)
O2A—C9A—C8A121.6 (7)O2B—C9B—C8B121.4 (7)
O3A—C9A—C8A115.1 (6)O3B—C9B—C8B114.9 (6)
O3A—C10A—H10A109.5O3B—C10B—H10D109.5
O3A—C10A—H10B109.5O3B—C10B—H10E109.5
H10A—C10A—H10B109.5H10D—C10B—H10E109.5
O3A—C10A—H10C109.5O3B—C10B—H10F109.5
H10A—C10A—H10C109.5H10D—C10B—H10F109.5
H10B—C10A—H10C109.5H10E—C10B—H10F109.5
N1A—C11A—C12A114.9 (7)N1B—C11B—C12B116.7 (7)
N1A—C11A—H11A108.6N1B—C11B—H11C108.1
C12A—C11A—H11A108.6C12B—C11B—H11C108.1
N1A—C11A—H11B108.6N1B—C11B—H11D108.1
C12A—C11A—H11B108.6C12B—C11B—H11D108.1
H11A—C11A—H11B107.5H11C—C11B—H11D107.3
C13A—C12A—C11A125.7 (9)C13B—C12B—C11B125.2 (8)
C13A—C12A—H12A117.2C13B—C12B—H12B117.4
C11A—C12A—H12A117.2C11B—C12B—H12B117.4
C12A—C13A—H13A120.0C12B—C13B—H13C120.0
C12A—C13A—H13B120.0C12B—C13B—H13D120.0
H13A—C13A—H13B120.0H13C—C13B—H13D120.0
O5A—S1A—N1A—C1A167.7 (5)O4B—S1B—N1B—C1B64.2 (5)
O4A—S1A—N1A—C1A61.2 (5)O5B—S1B—N1B—C1B167.3 (5)
C8A—S1A—N1A—C1A51.4 (5)C8B—S1B—N1B—C1B49.4 (5)
O5A—S1A—N1A—C11A0.2 (6)O4B—S1B—N1B—C11B119.2 (5)
O4A—S1A—N1A—C11A131.4 (5)O5B—S1B—N1B—C11B9.3 (6)
C8A—S1A—N1A—C11A116.0 (5)C8B—S1B—N1B—C11B127.1 (5)
C11A—N1A—C1A—C2A44.4 (8)C11B—N1B—C1B—C6B143.2 (6)
S1A—N1A—C1A—C2A148.1 (5)S1B—N1B—C1B—C6B33.2 (7)
C11A—N1A—C1A—C6A132.4 (6)C11B—N1B—C1B—C2B32.6 (9)
S1A—N1A—C1A—C6A35.1 (7)S1B—N1B—C1B—C2B150.9 (5)
C6A—C1A—C2A—C3A3.5 (9)C6B—C1B—C2B—C3B2.5 (9)
N1A—C1A—C2A—C3A179.7 (6)N1B—C1B—C2B—C3B178.2 (5)
C1A—C2A—C3A—C4A1.6 (10)C1B—C2B—C3B—C4B1.8 (9)
C2A—C3A—C4A—C5A1.3 (11)C2B—C3B—C4B—C5B0.6 (9)
C3A—C4A—C5A—C6A2.2 (10)C3B—C4B—C5B—C6B0.2 (9)
C4A—C5A—C6A—C1A0.3 (9)C2B—C1B—C6B—C5B2.0 (8)
C4A—C5A—C6A—C7A175.5 (6)N1B—C1B—C6B—C5B177.7 (5)
C2A—C1A—C6A—C5A2.6 (9)C2B—C1B—C6B—C7B173.3 (6)
N1A—C1A—C6A—C5A179.4 (5)N1B—C1B—C6B—C7B2.5 (8)
C2A—C1A—C6A—C7A172.6 (5)C4B—C5B—C6B—C1B0.8 (8)
N1A—C1A—C6A—C7A4.1 (8)C4B—C5B—C6B—C7B174.5 (6)
C5A—C6A—C7A—O1A15.4 (8)C1B—C6B—C7B—O1B165.1 (5)
C1A—C6A—C7A—O1A159.8 (5)C5B—C6B—C7B—O1B9.9 (8)
C5A—C6A—C7A—C8A166.3 (6)C1B—C6B—C7B—C8B13.5 (9)
C1A—C6A—C7A—C8A18.6 (9)C5B—C6B—C7B—C8B171.5 (5)
O1A—C7A—C8A—C9A1.1 (9)O1B—C7B—C8B—C9B2.4 (9)
C6A—C7A—C8A—C9A177.1 (5)C6B—C7B—C8B—C9B176.1 (5)
O1A—C7A—C8A—S1A175.3 (5)O1B—C7B—C8B—S1B170.5 (4)
C6A—C7A—C8A—S1A6.4 (8)C6B—C7B—C8B—S1B11.1 (8)
O5A—S1A—C8A—C7A150.2 (5)O4B—S1B—C8B—C7B76.5 (5)
O4A—S1A—C8A—C7A76.4 (5)O5B—S1B—C8B—C7B151.2 (4)
N1A—S1A—C8A—C7A37.3 (5)N1B—S1B—C8B—C7B37.6 (5)
O5A—S1A—C8A—C9A33.4 (6)O4B—S1B—C8B—C9B96.3 (5)
O4A—S1A—C8A—C9A100.1 (5)O5B—S1B—C8B—C9B36.0 (6)
N1A—S1A—C8A—C9A146.2 (5)N1B—S1B—C8B—C9B149.6 (5)
C10A—O3A—C9A—O2A4.1 (9)C10B—O3B—C9B—O2B3.3 (9)
C10A—O3A—C9A—C8A178.7 (5)C10B—O3B—C9B—C8B175.2 (5)
C7A—C8A—C9A—O2A2.2 (9)C7B—C8B—C9B—O2B0.2 (9)
S1A—C8A—C9A—O2A178.5 (5)S1B—C8B—C9B—O2B172.3 (5)
C7A—C8A—C9A—O3A175.0 (5)C7B—C8B—C9B—O3B178.3 (5)
S1A—C8A—C9A—O3A1.2 (8)S1B—C8B—C9B—O3B9.2 (8)
C1A—N1A—C11A—C12A103.1 (7)C1B—N1B—C11B—C12B97.5 (7)
S1A—N1A—C11A—C12A89.9 (7)S1B—N1B—C11B—C12B86.1 (7)
N1A—C11A—C12A—C13A8.8 (11)N1B—C11B—C12B—C13B10.2 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···O2A0.821.842.553 (8)144
O1B—H1OB···O2B0.821.872.588 (8)146
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1OA···O2A0.821.842.553 (8)144.2
O1B—H1OB···O2B0.821.872.588 (8)146.1
 

References

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First citationBürgi, H.-B. & Dunitz, J. D. (1994). Structure Correlation, Vol. 2, pp. 767–784. Weinheim: VCH.
First citationKleemann, A., Engel, J., Kutscher, B. & Reihert, D. (2008). Pharmaceutical Substances: Syntheses, Patents, Applications of the most relevant APIs, 5th ed. Stuttgart: Thieme.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
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