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The structure of the title compound, C
16H
22N
2O
6S, has been determined as part of an ongoing investigation into the preparation of
N-alkylated amino acid precursors for alkene cross-metathesis reactions for the generation of dynamic combinatorial libraries. The overall molecular conformation is stabilized by intramolecular C—H
O interactions.
Supporting information
CCDC reference: 236083
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.007 Å
- R factor = 0.040
- wR factor = 0.120
- Data-to-parameter ratio = 10.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.50 Ratio
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.45 Ratio
Alert level C
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... N1
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C11
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C14
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
PLAT368_ALERT_2_C Short C(sp2)-C(sp2) Bond C11 - C12 = 1.20 Ang.
Alert level G
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 27.50
From the CIF: _reflns_number_total 2353
Count of symmetry unique reflns 2355
Completeness (_total/calc) 99.92%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 0
Fraction of Friedel pairs measured 0.000
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 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
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: MSC/AFC7 Diffractometer Control for Windows
(Molecular Structure Corporation, 1999); cell refinement: MSC/AFC7 Diffractometer Control for Windows; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-2001); program(s) used to solve structure: TEXSAN for Windows; program(s) used to refine structure: TEXSAN for Windows and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: TEXSAN for Windows and PLATON (Spek, 2002).
Crystal data top
C16H22N2O6S | F(000) = 784 |
Mr = 370.43 | Dx = 1.288 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: C 2y | Cell parameters from 25 reflections |
a = 15.7515 (15) Å | θ = 12.9–16.9° |
b = 8.2452 (17) Å | µ = 0.20 mm−1 |
c = 15.673 (2) Å | T = 295 K |
β = 110.153 (9)° | Prismatic, colorless |
V = 1910.9 (5) Å3 | 0.35 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.025 |
Radiation source: Rigaku rotating anode | θmax = 27.5°, θmin = 2.6° |
Graphite monochromator | h = −8→20 |
ω–2θ scans | k = 0→10 |
2590 measured reflections | l = −20→19 |
2353 independent reflections | 3 standard reflections every 150 reflections |
1634 reflections with I > 2σ(I) | intensity decay: 1.4% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-atom parameters not refined |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0613P)2 + 0.3996P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.009 |
2353 reflections | Δρmax = 0.16 e Å−3 |
226 parameters | Δρmin = −0.21 e Å−3 |
1 restraint | Absolute structure: Flack (1983); 0 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.20 (12) |
Special details top
Experimental. The scan width was (1.73 + 0.30tanθ)° with an ω scan speed of 16° per minute
(up to 4 scans to achieve I/σ(I) > 10). Stationary background counts were
recorded at each end of the scan, and the scan time:background time ratio was
2:1. |
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
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 >
2σ(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 | x | y | z | Uiso*/Ueq | |
S1 | 0.87989 (6) | 0.01889 (12) | 0.29351 (6) | 0.0575 (3) | |
O1 | 0.6837 (4) | 0.3590 (5) | 0.2064 (3) | 0.128 (2) | |
O2 | 0.6639 (2) | 0.1012 (4) | 0.1950 (2) | 0.0810 (11) | |
O3 | 0.8531 (2) | 0.1087 (4) | 0.21093 (17) | 0.0704 (10) | |
O4 | 0.97305 (18) | 0.0122 (5) | 0.3487 (2) | 0.0846 (13) | |
O5 | 0.6828 (2) | −0.2526 (5) | 0.28698 (18) | 0.0779 (13) | |
O6 | 0.61864 (17) | −0.2870 (4) | 0.13735 (17) | 0.0640 (10) | |
N1 | 0.6944 (3) | 0.2207 (5) | 0.2375 (2) | 0.0711 (14) | |
N2 | 0.8464 (2) | −0.1659 (4) | 0.27196 (19) | 0.0532 (10) | |
C1 | 0.8260 (2) | 0.1102 (5) | 0.3656 (2) | 0.0525 (11) | |
C2 | 0.7496 (3) | 0.2049 (5) | 0.3349 (2) | 0.0569 (11) | |
C3 | 0.7186 (3) | 0.2917 (7) | 0.3941 (3) | 0.0779 (17) | |
C4 | 0.7636 (4) | 0.2734 (7) | 0.4867 (3) | 0.081 (2) | |
C5 | 0.8381 (3) | 0.1775 (6) | 0.5191 (2) | 0.0673 (15) | |
C6 | 0.8705 (3) | 0.0991 (6) | 0.4589 (2) | 0.0620 (14) | |
C7 | 0.7707 (2) | −0.2094 (4) | 0.1891 (2) | 0.0440 (10) | |
C8 | 0.6869 (2) | −0.2516 (5) | 0.2128 (2) | 0.0495 (12) | |
C9 | 0.5347 (3) | −0.3357 (8) | 0.1485 (4) | 0.095 (2) | |
C10 | 0.8832 (3) | −0.2895 (7) | 0.3431 (3) | 0.0768 (16) | |
C11 | 0.9702 (4) | −0.3644 (10) | 0.3427 (4) | 0.108 (3) | |
C12 | 0.9932 (7) | −0.5041 (13) | 0.3526 (9) | 0.198 (5) | |
C13 | 0.7977 (3) | −0.3415 (5) | 0.1363 (2) | 0.0564 (11) | |
C14 | 0.8729 (3) | −0.2980 (6) | 0.1010 (3) | 0.0716 (16) | |
C15 | 0.8455 (4) | −0.1675 (8) | 0.0293 (4) | 0.100 (2) | |
C16 | 0.9052 (5) | −0.4511 (11) | 0.0660 (4) | 0.130 (3) | |
H3 | 0.66780 | 0.36180 | 0.37170 | 0.0940* | |
H4 | 0.74210 | 0.32890 | 0.52840 | 0.0970* | |
H5 | 0.86750 | 0.16450 | 0.58270 | 0.0800* | |
H6 | 0.92420 | 0.03650 | 0.48160 | 0.0740* | |
H7 | 0.75640 | −0.11570 | 0.15150 | 0.0530* | |
H9A | 0.50680 | −0.24390 | 0.16440 | 0.1130* | |
H9B | 0.49530 | −0.38040 | 0.09310 | 0.1130* | |
H9C | 0.54680 | −0.41480 | 0.19520 | 0.1130* | |
H10A | 0.89390 | −0.24000 | 0.40060 | 0.0920* | |
H10B | 0.83950 | −0.37320 | 0.33430 | 0.0920* | |
H11 | 1.01280 | −0.29100 | 0.33380 | 0.1300* | |
H12A | 0.95370 | −0.58430 | 0.36150 | 0.2360* | |
H12B | 1.05060 | −0.53490 | 0.35050 | 0.2360* | |
H13A | 0.81670 | −0.43310 | 0.17500 | 0.0670* | |
H13B | 0.74580 | −0.36930 | 0.08560 | 0.0670* | |
H14 | 0.92210 | −0.25760 | 0.15070 | 0.0860* | |
H15A | 0.79550 | −0.20410 | −0.02090 | 0.1210* | |
H15B | 0.82890 | −0.07250 | 0.05400 | 0.1210* | |
H15C | 0.89480 | −0.14390 | 0.00960 | 0.1210* | |
H16A | 0.85890 | −0.48880 | 0.01290 | 0.1560* | |
H16B | 0.91910 | −0.53270 | 0.11150 | 0.1560* | |
H16C | 0.95780 | −0.42660 | 0.05180 | 0.1560* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0525 (5) | 0.0739 (7) | 0.0551 (5) | −0.0184 (5) | 0.0302 (4) | −0.0209 (5) |
O1 | 0.240 (6) | 0.064 (2) | 0.076 (2) | 0.034 (3) | 0.048 (3) | 0.0191 (18) |
O2 | 0.085 (2) | 0.071 (2) | 0.0709 (18) | −0.0003 (18) | 0.0064 (16) | −0.0101 (17) |
O3 | 0.0922 (19) | 0.0728 (19) | 0.0653 (15) | −0.0298 (16) | 0.0516 (15) | −0.0157 (14) |
O4 | 0.0502 (14) | 0.128 (3) | 0.0828 (18) | −0.023 (2) | 0.0323 (13) | −0.047 (2) |
O5 | 0.082 (2) | 0.103 (3) | 0.0657 (16) | −0.0038 (19) | 0.0472 (15) | 0.0045 (17) |
O6 | 0.0492 (14) | 0.0724 (19) | 0.0704 (16) | −0.0072 (14) | 0.0205 (12) | 0.0012 (15) |
N1 | 0.102 (3) | 0.051 (2) | 0.0605 (19) | 0.016 (2) | 0.0283 (19) | 0.0058 (19) |
N2 | 0.0541 (15) | 0.058 (2) | 0.0462 (15) | −0.0024 (15) | 0.0156 (13) | −0.0075 (14) |
C1 | 0.0548 (19) | 0.060 (2) | 0.0513 (18) | −0.0163 (19) | 0.0292 (16) | −0.0158 (17) |
C2 | 0.071 (2) | 0.051 (2) | 0.0536 (19) | −0.0041 (19) | 0.0276 (17) | −0.0034 (17) |
C3 | 0.091 (3) | 0.077 (3) | 0.072 (3) | 0.018 (3) | 0.036 (2) | −0.010 (2) |
C4 | 0.099 (4) | 0.087 (4) | 0.066 (3) | 0.007 (3) | 0.040 (2) | −0.023 (3) |
C5 | 0.072 (3) | 0.088 (3) | 0.0466 (19) | −0.005 (2) | 0.0263 (18) | −0.013 (2) |
C6 | 0.054 (2) | 0.081 (3) | 0.0540 (19) | −0.008 (2) | 0.0223 (16) | −0.016 (2) |
C7 | 0.0485 (17) | 0.0445 (18) | 0.0422 (15) | −0.0033 (15) | 0.0198 (13) | −0.0026 (14) |
C8 | 0.054 (2) | 0.047 (2) | 0.055 (2) | 0.0023 (17) | 0.0285 (17) | 0.0049 (17) |
C9 | 0.053 (2) | 0.101 (4) | 0.133 (4) | −0.012 (3) | 0.036 (3) | 0.010 (4) |
C10 | 0.082 (3) | 0.086 (3) | 0.057 (2) | 0.018 (3) | 0.017 (2) | 0.009 (2) |
C11 | 0.081 (4) | 0.121 (6) | 0.103 (4) | 0.041 (4) | 0.007 (3) | 0.012 (4) |
C12 | 0.162 (8) | 0.139 (8) | 0.286 (12) | 0.080 (7) | 0.069 (9) | 0.071 (9) |
C13 | 0.062 (2) | 0.057 (2) | 0.0544 (19) | 0.0002 (18) | 0.0256 (17) | −0.0092 (18) |
C14 | 0.064 (2) | 0.100 (4) | 0.062 (2) | −0.003 (2) | 0.0360 (19) | −0.016 (2) |
C15 | 0.131 (4) | 0.117 (5) | 0.080 (3) | −0.009 (4) | 0.071 (3) | 0.006 (3) |
C16 | 0.138 (5) | 0.150 (7) | 0.137 (5) | 0.039 (5) | 0.093 (5) | −0.016 (5) |
Geometric parameters (Å, º) top
S1—O3 | 1.423 (3) | C14—C16 | 1.532 (10) |
S1—O4 | 1.425 (3) | C3—H3 | 0.9508 |
S1—N2 | 1.610 (3) | C4—H4 | 0.9507 |
S1—C1 | 1.796 (4) | C5—H5 | 0.9495 |
O1—N1 | 1.229 (6) | C6—H6 | 0.9493 |
O2—N1 | 1.194 (5) | C7—H7 | 0.9505 |
O5—C8 | 1.186 (4) | C9—H9A | 0.9506 |
O6—C8 | 1.328 (4) | C9—H9B | 0.9506 |
O6—C9 | 1.449 (6) | C9—H9C | 0.9494 |
N1—C2 | 1.479 (4) | C10—H10A | 0.9500 |
N2—C7 | 1.473 (4) | C10—H10B | 0.9506 |
N2—C10 | 1.474 (6) | C11—H11 | 0.9489 |
C1—C2 | 1.375 (6) | C12—H12A | 0.9506 |
C1—C6 | 1.390 (4) | C12—H12B | 0.9505 |
C2—C3 | 1.387 (6) | C13—H13A | 0.9502 |
C3—C4 | 1.387 (6) | C13—H13B | 0.9511 |
C4—C5 | 1.360 (8) | C14—H14 | 0.9499 |
C5—C6 | 1.379 (6) | C15—H15A | 0.9505 |
C7—C8 | 1.529 (5) | C15—H15B | 0.9495 |
C7—C13 | 1.515 (5) | C15—H15C | 0.9494 |
C10—C11 | 1.505 (9) | C16—H16A | 0.9502 |
C11—C12 | 1.201 (14) | C16—H16B | 0.9495 |
C13—C14 | 1.513 (7) | C16—H16C | 0.9507 |
C14—C15 | 1.508 (8) | | |
| | | |
S1···O2 | 3.286 (3) | C9···H16Bviii | 3.0275 |
O1···O6i | 3.159 (5) | C10···H13A | 2.7457 |
O1···C8i | 3.212 (6) | C11···H13A | 2.9489 |
O1···C9i | 3.347 (8) | C11···H14 | 2.9722 |
O2···C8 | 2.933 (5) | C13···H10B | 2.9537 |
O2···O3 | 2.904 (5) | C15···H7 | 2.7699 |
O2···O5 | 3.222 (5) | C15···H13Bix | 3.0939 |
O2···S1 | 3.286 (3) | C16···H9Ax | 3.0112 |
O2···C7 | 3.083 (5) | H3···O1 | 2.6874 |
O3···N1 | 2.827 (6) | H4···O5vi | 2.8045 |
O3···O2 | 2.904 (5) | H4···C6vi | 2.8969 |
O3···C9ii | 3.358 (6) | H5···O4iii | 2.6796 |
O4···C5iii | 3.279 (5) | H5···O5vi | 2.5262 |
O4···C6iii | 3.249 (5) | H6···O4 | 2.4648 |
O4···C11 | 3.106 (9) | H6···H10A | 2.5728 |
O5···O2 | 3.222 (5) | H6···O4iii | 2.6014 |
O5···C5iv | 3.220 (5) | H6···C6iii | 3.0847 |
O5···N2 | 2.761 (5) | H6···H6iii | 2.2552 |
O5···C4iv | 3.358 (5) | H7···O2 | 2.5437 |
O5···C10 | 2.986 (6) | H7···O3 | 2.3735 |
O6···O1v | 3.159 (5) | H7···C15 | 2.7699 |
O1···H13Ai | 2.8775 | H7···H15B | 2.2290 |
O1···H3 | 2.6874 | H9A···O5 | 2.7770 |
O1···H9Ci | 2.8104 | H9A···C16viii | 3.0112 |
O2···H7 | 2.5437 | H9A···H16Bviii | 2.1998 |
O3···H15B | 2.7894 | H9C···O1v | 2.8104 |
O3···H7 | 2.3735 | H9C···O5 | 2.5147 |
O4···H5iii | 2.6796 | H10A···O4 | 2.6905 |
O4···H10A | 2.6905 | H10A···C1 | 3.0624 |
O4···H11 | 2.6071 | H10A···C6 | 3.0034 |
O4···H6 | 2.4648 | H10A···H6 | 2.5728 |
O4···H6iii | 2.6014 | H10B···O5 | 2.5238 |
O5···H10B | 2.5238 | H10B···C8 | 2.6935 |
O5···H9C | 2.5147 | H10B···C13 | 2.9537 |
O5···H4iv | 2.8045 | H10B···H12A | 2.4328 |
O5···H5iv | 2.5262 | H10B···H13A | 2.4472 |
O5···H9A | 2.7770 | H11···O4 | 2.6071 |
O6···H13B | 2.4999 | H12A···H10B | 2.4328 |
N1···O3 | 2.827 (6) | H13A···O1v | 2.8775 |
N2···O5 | 2.761 (5) | H13A···C10 | 2.7457 |
N2···H14 | 2.6771 | H13A···C11 | 2.9489 |
C4···O5vi | 3.358 (5) | H13A···H10B | 2.4472 |
C5···O5vi | 3.220 (5) | H13A···H16B | 2.3179 |
C5···O4iii | 3.279 (5) | H13B···O6 | 2.4999 |
C6···O4iii | 3.249 (5) | H13B···H15A | 2.4809 |
C7···O2 | 3.083 (5) | H13B···C15xi | 3.0939 |
C8···O2 | 2.933 (5) | H14···N2 | 2.6771 |
C8···O1v | 3.212 (6) | H14···C11 | 2.9722 |
C9···O3vii | 3.358 (6) | H15A···H13B | 2.4809 |
C9···O1v | 3.347 (8) | H15A···H16A | 2.5345 |
C10···O5 | 2.986 (6) | H15B···O3 | 2.7894 |
C11···C13 | 3.439 (7) | H15B···C7 | 2.8170 |
C11···O4 | 3.106 (9) | H15B···H7 | 2.2290 |
C13···C11 | 3.439 (7) | H15C···H16C | 2.5304 |
C1···H10A | 3.0624 | H16A···H15A | 2.5345 |
C6···H6iii | 3.0847 | H16B···H13A | 2.3179 |
C6···H10A | 3.0034 | H16B···C9x | 3.0275 |
C6···H4iv | 2.8969 | H16B···H9Ax | 2.1998 |
C7···H15B | 2.8170 | H16C···H15C | 2.5304 |
C8···H10B | 2.6935 | H16C···H16Cxii | 2.4272 |
| | | |
O3—S1—O4 | 119.5 (2) | C1—C6—H6 | 119.43 |
O3—S1—N2 | 109.19 (17) | C5—C6—H6 | 119.38 |
O3—S1—C1 | 107.32 (18) | N2—C7—H7 | 107.20 |
O4—S1—N2 | 106.6 (2) | C8—C7—H7 | 107.19 |
O4—S1—C1 | 104.21 (17) | C13—C7—H7 | 107.27 |
N2—S1—C1 | 109.70 (18) | O6—C9—H9A | 109.54 |
C8—O6—C9 | 116.5 (3) | O6—C9—H9B | 109.45 |
O1—N1—O2 | 124.8 (4) | O6—C9—H9C | 109.53 |
O1—N1—C2 | 116.3 (4) | H9A—C9—H9B | 109.44 |
O2—N1—C2 | 118.9 (4) | H9A—C9—H9C | 109.45 |
S1—N2—C7 | 121.5 (2) | H9B—C9—H9C | 109.41 |
S1—N2—C10 | 118.7 (3) | N2—C10—H10A | 108.39 |
C7—N2—C10 | 119.1 (3) | N2—C10—H10B | 108.41 |
S1—C1—C2 | 124.4 (2) | C11—C10—H10A | 108.42 |
S1—C1—C6 | 117.3 (3) | C11—C10—H10B | 108.44 |
C2—C1—C6 | 118.0 (3) | H10A—C10—H10B | 109.42 |
N1—C2—C1 | 122.9 (3) | C10—C11—H11 | 115.46 |
N1—C2—C3 | 115.3 (4) | C12—C11—H11 | 115.68 |
C1—C2—C3 | 121.8 (3) | C11—C12—H12A | 120.16 |
C2—C3—C4 | 118.2 (5) | C11—C12—H12B | 119.99 |
C3—C4—C5 | 121.2 (5) | H12A—C12—H12B | 119.85 |
C4—C5—C6 | 119.5 (3) | C7—C13—H13A | 107.99 |
C1—C6—C5 | 121.2 (4) | C7—C13—H13B | 107.90 |
N2—C7—C8 | 110.2 (3) | C14—C13—H13A | 107.92 |
N2—C7—C13 | 111.2 (3) | C14—C13—H13B | 107.91 |
C8—C7—C13 | 113.4 (3) | H13A—C13—H13B | 109.44 |
O5—C8—O6 | 124.8 (3) | C13—C14—H14 | 107.67 |
O5—C8—C7 | 125.6 (3) | C15—C14—H14 | 107.71 |
O6—C8—C7 | 109.6 (3) | C16—C14—H14 | 107.75 |
N2—C10—C11 | 113.7 (4) | C14—C15—H15A | 109.46 |
C10—C11—C12 | 128.9 (8) | C14—C15—H15B | 109.46 |
C7—C13—C14 | 115.6 (4) | C14—C15—H15C | 109.42 |
C13—C14—C15 | 112.5 (4) | H15A—C15—H15B | 109.47 |
C13—C14—C16 | 109.5 (5) | H15A—C15—H15C | 109.46 |
C15—C14—C16 | 111.5 (4) | H15B—C15—H15C | 109.54 |
C2—C3—H3 | 120.81 | C14—C16—H16A | 109.51 |
C4—C3—H3 | 120.95 | C14—C16—H16B | 109.52 |
C3—C4—H4 | 119.50 | C14—C16—H16C | 109.42 |
C5—C4—H4 | 119.28 | H16A—C16—H16B | 109.56 |
C4—C5—H5 | 120.24 | H16A—C16—H16C | 109.41 |
C6—C5—H5 | 120.26 | H16B—C16—H16C | 109.41 |
| | | |
O3—S1—N2—C7 | −22.6 (3) | S1—N2—C10—C11 | −87.4 (5) |
O3—S1—N2—C10 | 166.7 (3) | C7—N2—C10—C11 | 101.7 (5) |
O4—S1—N2—C7 | −153.0 (3) | S1—C1—C2—C3 | −170.3 (4) |
O4—S1—N2—C10 | 36.3 (4) | S1—C1—C2—N1 | 10.3 (6) |
C1—S1—N2—C7 | 94.7 (3) | S1—C1—C6—C5 | 174.3 (4) |
C1—S1—N2—C10 | −76.0 (3) | C6—C1—C2—N1 | −177.4 (4) |
O3—S1—C1—C2 | 21.9 (4) | C6—C1—C2—C3 | 2.1 (7) |
O3—S1—C1—C6 | −150.5 (3) | C2—C1—C6—C5 | 1.4 (7) |
O4—S1—C1—C2 | 149.6 (4) | C1—C2—C3—C4 | −3.9 (8) |
O4—S1—C1—C6 | −22.8 (4) | N1—C2—C3—C4 | 175.6 (5) |
N2—S1—C1—C2 | −96.6 (4) | C2—C3—C4—C5 | 2.3 (8) |
N2—S1—C1—C6 | 91.0 (4) | C3—C4—C5—C6 | 1.1 (8) |
C9—O6—C8—O5 | −2.3 (7) | C4—C5—C6—C1 | −3.0 (8) |
C9—O6—C8—C7 | 177.8 (4) | N2—C7—C8—O5 | −1.3 (6) |
O2—N1—C2—C3 | −122.5 (5) | C13—C7—C8—O6 | −55.9 (4) |
O1—N1—C2—C3 | 57.6 (7) | N2—C7—C13—C14 | −62.4 (4) |
O2—N1—C2—C1 | 56.9 (7) | C8—C7—C13—C14 | 172.7 (3) |
O1—N1—C2—C1 | −122.9 (6) | N2—C7—C8—O6 | 178.6 (3) |
S1—N2—C7—C8 | −106.8 (3) | C13—C7—C8—O5 | 124.2 (4) |
S1—N2—C7—C13 | 126.5 (3) | N2—C10—C11—C12 | −138.1 (10) |
C10—N2—C7—C8 | 63.8 (4) | C7—C13—C14—C16 | 169.0 (4) |
C10—N2—C7—C13 | −62.9 (4) | C7—C13—C14—C15 | −66.4 (5) |
Symmetry codes: (i) x, y+1, z; (ii) x+1/2, y+1/2, z; (iii) −x+2, y, −z+1; (iv) −x+3/2, y−1/2, −z+1; (v) x, y−1, z; (vi) −x+3/2, y+1/2, −z+1; (vii) x−1/2, y−1/2, z; (viii) x−1/2, y+1/2, z; (ix) −x+3/2, y+1/2, −z; (x) x+1/2, y−1/2, z; (xi) −x+3/2, y−1/2, −z; (xii) −x+2, y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O5vi | 0.95 | 2.53 | 3.220 (5) | 130 |
C6—H6···O4 | 0.95 | 2.46 | 2.833 (5) | 103 |
C7—H7···O2 | 0.95 | 2.54 | 3.083 (5) | 116 |
C7—H7···O3 | 0.95 | 2.37 | 2.894 (5) | 114 |
C10—H10B···O5 | 0.95 | 2.52 | 2.986 (6) | 110 |
C13—H13B···O6 | 0.95 | 2.50 | 2.862 (6) | 103 |
Symmetry code: (vi) −x+3/2, y+1/2, −z+1. |
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