Ethyl 2-[(1,7,7-trimethyl­bicyclo­[2.2.1]hept-2-yl­idene)hydrazono]-2-(4-nitro­phenyl­sulfan­yl)acetate

Heating ethyl 4,5-dihydro-4-(4-nitro­phen­yl)-spiro­[1,3,4-thia­diazole-5,2'-camphane]-2-carboxyl­ate in methanol provided the unusual rearrangement product (C₉H₁₉)N₂C(SC₆H₄NO₂)(COOC₂H₅) or C₂₀H₂₅N₃O₄S, whose structure was confirmed by an X-ray diffraction study. The structure features a camphor group connected through a hydrazine fragment to a nitro­phenyl­sulfanyl group and an ethoxy­carbonyl group.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C) = 0.009 Å
• Disorder in main residue
• R factor = 0.089
• wR factor = 0.255
• Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for       C23B

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.255
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.123
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT213_ALERT_2_C Atom C23B    has ADP max/min Ratio .............       4.00 prolat
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         C2
PLAT301_ALERT_3_C Main Residue  Disorder .........................       7.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         12
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      23.70 Deg.
              C23B -O22  -C23     1.555   1.555   1.555
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.20

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               3710
           Count of symmetry unique reflns         2145
           Completeness (_total/calc)            172.96%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1565
           Fraction of Friedel pairs measured     0.730
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  11 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
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Ethyl 2-[(1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene)hydrazono]- 2-(4-nitrophenylsulfanyl)acetate

Crystal data

C20H25N3O4S	F(000) = 856
Mr = 403.49	Dx = 1.273 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2834 reflections
a = 6.9124 (14) Å	θ = 3.1–31.0°
b = 15.398 (3) Å	µ = 0.18 mm^−1
c = 19.778 (4) Å	T = 180 K
V = 2105.2 (7) Å^3	Block, colorless
Z = 4	0.55 × 0.32 × 0.20 mm

Data collection

Oxford Diffraction XCALIBUR diffractometer	3710 independent reflections
Radiation source: fine-focus sealed tube	2657 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.123
ω and φ scans	θmax = 25.0°, θmin = 3.1°
Absorption correction: multi-scan (Blessing, 1995)	h = −8→7
Tmin = 0.890, Tmax = 0.956	k = −17→18
14039 measured reflections	l = −23→22

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.089	w = 1/[σ^2(Fo^2) + (0.1461P)^2 + 0.054P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.255	(Δ/σ)max = 0.002
S = 1.13	Δρmax = 0.36 e Å^−3
3710 reflections	Δρmin = −0.34 e Å^−3
279 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
4 restraints	Extinction coefficient: 0.026 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0 (2)

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	Occ. (<1)
S1	1.0952 (3)	0.91945 (10)	−0.01821 (8)	0.0685 (6)
N3	0.8496 (8)	1.0403 (4)	0.0216 (3)	0.0641 (13)
N4	0.7700 (7)	1.0198 (3)	−0.0413 (2)	0.0583 (12)
O21	0.9953 (8)	0.9894 (5)	0.1576 (3)	0.109 (2)
C1'	0.6084 (8)	1.0801 (3)	−0.1414 (3)	0.0488 (12)
C2	0.9921 (8)	0.9938 (3)	0.0374 (3)	0.0480 (12)
C3'	0.7060 (10)	1.1796 (4)	−0.0520 (4)	0.0669 (17)
H3'A	0.8372	1.2006	−0.0460	0.080*
H3'B	0.6328	1.1892	−0.0109	0.080*
C4'	0.6077 (11)	1.2216 (4)	−0.1137 (4)	0.0719 (18)
H4'	0.5544	1.2795	−0.1051	0.086*
C5	0.7021 (7)	1.0841 (3)	−0.0736 (3)	0.0480 (12)
C5'	0.7564 (12)	1.2187 (5)	−0.1701 (4)	0.087 (2)
H5'A	0.8825	1.2376	−0.1543	0.104*
H5'B	0.7174	1.2545	−0.2081	0.104*
C6'	0.7580 (10)	1.1197 (5)	−0.1896 (4)	0.0730 (18)
H6'A	0.7203	1.1113	−0.2364	0.088*
H6'B	0.8849	1.0944	−0.1825	0.088*
C7'	0.4581 (8)	1.1548 (3)	−0.1359 (3)	0.0527 (13)
C8'	0.3053 (10)	1.1386 (5)	−0.0827 (3)	0.0701 (17)
H8'A	0.3648	1.1144	−0.0430	0.105*
H8'B	0.2109	1.0986	−0.0999	0.105*
H8'C	0.2432	1.1924	−0.0712	0.105*
C9'	0.3590 (10)	1.1763 (5)	−0.2023 (4)	0.0735 (18)
H9'A	0.2792	1.2268	−0.1965	0.110*
H9'B	0.2801	1.1281	−0.2160	0.110*
H9'C	0.4549	1.1876	−0.2363	0.110*
C10'	0.5422 (10)	0.9897 (4)	−0.1622 (3)	0.0628 (16)
H10A	0.6491	0.9501	−0.1593	0.094*
H10B	0.4952	0.9914	−0.2079	0.094*
H10C	0.4405	0.9708	−0.1327	0.094*
C21	1.0774 (10)	1.0062 (4)	0.1066 (3)	0.0611 (15)
O22	1.2556 (7)	1.0365 (3)	0.1037 (2)	0.0678 (12)
C23	1.3493 (16)	1.0344 (9)	0.1710 (5)	0.064 (3)	0.70
H23A	1.2844	1.0735	0.2020	0.077*	0.70
H23B	1.3464	0.9762	0.1896	0.077*	0.70
C24	1.5501 (13)	1.0627 (8)	0.1592 (5)	0.074 (3)	0.70
H24A	1.6179	1.0188	0.1342	0.111*	0.70
H24B	1.6133	1.0719	0.2018	0.111*	0.70
H24C	1.5499	1.1159	0.1339	0.111*	0.70
C23B	1.369 (5)	1.0699 (16)	0.1599 (19)	0.110 (19)	0.30
H23C	1.2856	1.0896	0.1963	0.132*	0.30
H23D	1.4507	1.1176	0.1455	0.132*	0.30
C24B	1.486 (3)	0.9949 (12)	0.1812 (9)	0.057 (5)	0.30
H24D	1.4017	0.9485	0.1949	0.085*	0.30
H24E	1.5669	1.0114	0.2185	0.085*	0.30
H24F	1.5649	0.9759	0.1442	0.085*	0.30
C111	1.2505 (9)	0.8609 (3)	0.0361 (3)	0.0527 (13)
C112	1.4514 (8)	0.8635 (3)	0.0244 (3)	0.0532 (13)
H112	1.5026	0.8980	−0.0098	0.064*
C113	1.5689 (8)	0.8145 (4)	0.0644 (3)	0.0567 (14)
H113	1.7019	0.8160	0.0575	0.068*
C114	1.4944 (8)	0.7625 (3)	0.1149 (3)	0.0454 (11)
C115	1.2960 (8)	0.7576 (4)	0.1269 (3)	0.0548 (14)
H115	1.2448	0.7217	0.1602	0.066*
C116	1.1789 (8)	0.8090 (4)	0.0865 (3)	0.0590 (15)
H116	1.0460	0.8082	0.0939	0.071*
N1	1.6228 (8)	0.7091 (3)	0.1564 (2)	0.0567 (12)
O1	1.5486 (7)	0.6590 (3)	0.1971 (2)	0.0794 (14)
O2	1.7957 (8)	0.7150 (3)	0.1473 (3)	0.0834 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.1007 (13)	0.0539 (8)	0.0507 (8)	0.0238 (8)	−0.0173 (8)	−0.0086 (7)
N3	0.075 (3)	0.064 (3)	0.053 (3)	0.019 (3)	−0.001 (2)	−0.004 (2)
N4	0.070 (3)	0.058 (3)	0.047 (3)	0.014 (2)	−0.016 (2)	−0.001 (2)
O21	0.106 (4)	0.175 (7)	0.047 (3)	0.036 (4)	−0.012 (3)	0.002 (3)
C1'	0.058 (3)	0.041 (2)	0.047 (3)	0.001 (2)	−0.004 (2)	−0.003 (2)
C2	0.057 (3)	0.038 (2)	0.049 (3)	0.006 (2)	−0.007 (2)	−0.002 (2)
C3'	0.082 (4)	0.045 (3)	0.074 (4)	−0.010 (3)	−0.026 (3)	0.000 (3)
C4'	0.089 (5)	0.041 (3)	0.086 (5)	−0.005 (3)	−0.018 (4)	0.004 (3)
C5	0.053 (3)	0.041 (2)	0.050 (3)	0.000 (2)	−0.009 (2)	0.000 (2)
C5'	0.087 (5)	0.078 (5)	0.095 (5)	−0.031 (4)	−0.020 (4)	0.029 (4)
C6'	0.070 (4)	0.089 (5)	0.060 (4)	0.003 (4)	−0.001 (3)	0.013 (3)
C7'	0.059 (3)	0.044 (3)	0.055 (3)	−0.003 (2)	−0.008 (2)	0.006 (2)
C8'	0.072 (4)	0.070 (4)	0.068 (4)	0.005 (3)	−0.001 (3)	−0.005 (3)
C9'	0.081 (4)	0.065 (4)	0.074 (4)	0.015 (3)	−0.022 (3)	0.011 (3)
C10'	0.088 (4)	0.042 (3)	0.059 (3)	0.000 (3)	−0.020 (3)	−0.005 (2)
C21	0.072 (4)	0.067 (4)	0.044 (3)	0.020 (3)	−0.015 (3)	−0.008 (3)
O22	0.083 (3)	0.049 (2)	0.071 (3)	0.008 (2)	−0.021 (2)	−0.016 (2)
C23	0.077 (7)	0.051 (8)	0.064 (6)	0.009 (6)	−0.011 (5)	−0.019 (5)
C24	0.065 (6)	0.082 (7)	0.075 (6)	0.010 (5)	−0.008 (5)	−0.014 (5)
C23B	0.14 (3)	0.034 (15)	0.16 (3)	0.045 (17)	−0.12 (3)	−0.043 (17)
C24B	0.085 (14)	0.037 (9)	0.048 (10)	0.013 (11)	−0.002 (9)	0.000 (8)
C111	0.079 (4)	0.032 (2)	0.047 (3)	0.001 (2)	−0.009 (3)	−0.004 (2)
C112	0.068 (4)	0.034 (2)	0.058 (3)	0.004 (2)	−0.003 (3)	0.013 (2)
C113	0.049 (3)	0.050 (3)	0.071 (4)	0.003 (2)	0.005 (3)	0.015 (3)
C114	0.057 (3)	0.030 (2)	0.049 (3)	−0.003 (2)	−0.004 (2)	−0.004 (2)
C115	0.064 (4)	0.043 (3)	0.058 (3)	−0.005 (2)	−0.005 (3)	0.005 (2)
C116	0.046 (3)	0.058 (3)	0.073 (4)	−0.002 (3)	0.003 (3)	0.009 (3)
N1	0.068 (3)	0.044 (2)	0.058 (3)	0.003 (2)	−0.001 (2)	0.002 (2)
O1	0.096 (3)	0.069 (3)	0.072 (3)	0.007 (3)	−0.006 (3)	0.028 (3)
O2	0.078 (3)	0.075 (3)	0.097 (4)	0.018 (3)	−0.001 (3)	0.026 (3)

Geometric parameters (Å, º)

S1—C2	1.741 (5)	C10'—H10A	0.9600
S1—C111	1.766 (6)	C10'—H10B	0.9600
N3—C2	1.257 (7)	C10'—H10C	0.9600
N3—N4	1.397 (7)	C21—O22	1.319 (8)
N4—C5	1.269 (7)	O22—C23B	1.453 (16)
O21—C21	1.187 (8)	O22—C23	1.480 (11)
C1'—C5	1.489 (7)	C23—C24	1.473 (13)
C1'—C10'	1.521 (8)	C23—H23A	0.9700
C1'—C6'	1.533 (9)	C23—H23B	0.9700
C1'—C7'	1.555 (8)	C24—H24A	0.9600
C2—C21	1.502 (8)	C24—H24B	0.9600
C3'—C5	1.531 (8)	C24—H24C	0.9600
C3'—C4'	1.539 (9)	C23B—C24B	1.471 (18)
C3'—H3'A	0.9700	C23B—H23C	0.9700
C3'—H3'B	0.9700	C23B—H23D	0.9700
C4'—C5'	1.517 (12)	C24B—H24D	0.9600
C4'—C7'	1.522 (8)	C24B—H24E	0.9600
C4'—H4'	0.9800	C24B—H24F	0.9600
C5'—C6'	1.573 (12)	C111—C116	1.370 (8)
C5'—H5'A	0.9700	C111—C112	1.408 (9)
C5'—H5'B	0.9700	C112—C113	1.362 (8)
C6'—H6'A	0.9700	C112—H112	0.9300
C6'—H6'B	0.9700	C113—C114	1.380 (8)
C7'—C8'	1.512 (9)	C113—H113	0.9300
C7'—C9'	1.517 (8)	C114—C115	1.393 (8)
C8'—H8'A	0.9600	C114—N1	1.462 (7)
C8'—H8'B	0.9600	C115—C116	1.385 (8)
C8'—H8'C	0.9600	C115—H115	0.9300
C9'—H9'A	0.9600	C116—H116	0.9300
C9'—H9'B	0.9600	N1—O2	1.212 (7)
C9'—H9'C	0.9600	N1—O1	1.227 (6)
C2—S1—C111	101.6 (3)	C7'—C9'—H9'C	109.5
C2—N3—N4	113.7 (5)	H9'A—C9'—H9'C	109.5
C5—N4—N3	114.7 (5)	H9'B—C9'—H9'C	109.5
C5—C1'—C10'	114.4 (5)	C1'—C10'—H10A	109.5
C5—C1'—C6'	104.5 (5)	C1'—C10'—H10B	109.5
C10'—C1'—C6'	113.4 (5)	H10A—C10'—H10B	109.5
C5—C1'—C7'	101.4 (4)	C1'—C10'—H10C	109.5
C10'—C1'—C7'	119.7 (5)	H10A—C10'—H10C	109.5
C6'—C1'—C7'	101.5 (4)	H10B—C10'—H10C	109.5
N3—C2—C21	117.6 (5)	O21—C21—O22	124.1 (6)
N3—C2—S1	122.6 (4)	O21—C21—C2	124.0 (6)
C21—C2—S1	119.9 (4)	O22—C21—C2	111.9 (5)
C5—C3'—C4'	100.1 (5)	C21—O22—C23B	127 (2)
C5—C3'—H3'A	111.8	C21—O22—C23	111.2 (6)
C4'—C3'—H3'A	111.8	C23B—O22—C23	23.7 (14)
C5—C3'—H3'B	111.8	C24—C23—O22	105.3 (8)
C4'—C3'—H3'B	111.8	C24—C23—H23A	110.7
H3'A—C3'—H3'B	109.5	O22—C23—H23A	110.7
C5'—C4'—C7'	103.2 (6)	C24—C23—H23B	110.7
C5'—C4'—C3'	105.7 (6)	O22—C23—H23B	110.7
C7'—C4'—C3'	104.1 (5)	H23A—C23—H23B	108.8
C5'—C4'—H4'	114.2	O22—C23B—C24B	103.8 (15)
C7'—C4'—H4'	114.2	O22—C23B—H23C	111.0
C3'—C4'—H4'	114.2	C24B—C23B—H23C	111.0
N4—C5—C1'	125.5 (5)	O22—C23B—H23D	111.0
N4—C5—C3'	127.1 (5)	C24B—C23B—H23D	111.0
C1'—C5—C3'	107.4 (4)	H23C—C23B—H23D	109.0
C4'—C5'—C6'	102.3 (6)	C23B—C24B—H24D	109.5
C4'—C5'—H5'A	111.3	C23B—C24B—H24E	109.5
C6'—C5'—H5'A	111.3	H24D—C24B—H24E	109.5
C4'—C5'—H5'B	111.3	C23B—C24B—H24F	109.5
C6'—C5'—H5'B	111.3	H24D—C24B—H24F	109.5
H5'A—C5'—H5'B	109.2	H24E—C24B—H24F	109.5
C1'—C6'—C5'	103.2 (6)	C116—C111—C112	119.5 (5)
C1'—C6'—H6'A	111.1	C116—C111—S1	121.4 (5)
C5'—C6'—H6'A	111.1	C112—C111—S1	119.0 (4)
C1'—C6'—H6'B	111.1	C113—C112—C111	118.5 (5)
C5'—C6'—H6'B	111.1	C113—C112—H112	120.8
H6'A—C6'—H6'B	109.1	C111—C112—H112	120.8
C8'—C7'—C9'	108.8 (5)	C112—C113—C114	121.3 (5)
C8'—C7'—C4'	112.7 (5)	C112—C113—H113	119.4
C9'—C7'—C4'	114.1 (5)	C114—C113—H113	119.4
C8'—C7'—C1'	113.1 (5)	C113—C114—C115	121.4 (5)
C9'—C7'—C1'	113.8 (5)	C113—C114—N1	120.4 (5)
C4'—C7'—C1'	93.8 (4)	C115—C114—N1	118.2 (5)
C7'—C8'—H8'A	109.5	C116—C115—C114	116.5 (5)
C7'—C8'—H8'B	109.5	C116—C115—H115	121.7
H8'A—C8'—H8'B	109.5	C114—C115—H115	121.7
C7'—C8'—H8'C	109.5	C111—C116—C115	122.8 (6)
H8'A—C8'—H8'C	109.5	C111—C116—H116	118.6
H8'B—C8'—H8'C	109.5	C115—C116—H116	118.6
C7'—C9'—H9'A	109.5	O2—N1—O1	123.8 (5)
C7'—C9'—H9'B	109.5	O2—N1—C114	118.3 (5)
H9'A—C9'—H9'B	109.5	O1—N1—C114	117.9 (5)
C2—N3—N4—C5	−146.2 (6)	C10'—C1'—C7'—C9'	−62.2 (7)
N4—N3—C2—C21	−175.2 (5)	C6'—C1'—C7'—C9'	63.5 (6)
N4—N3—C2—S1	6.7 (8)	C5—C1'—C7'—C4'	52.5 (5)
C111—S1—C2—N3	−168.9 (5)	C10'—C1'—C7'—C4'	179.3 (5)
C111—S1—C2—C21	12.9 (5)	C6'—C1'—C7'—C4'	−55.0 (5)
C5—C3'—C4'—C5'	−73.5 (6)	N3—C2—C21—O21	66.1 (9)
C5—C3'—C4'—C7'	34.9 (7)	S1—C2—C21—O21	−115.7 (7)
N3—N4—C5—C1'	−179.6 (5)	N3—C2—C21—O22	−114.9 (6)
N3—N4—C5—C3'	2.4 (9)	S1—C2—C21—O22	63.3 (6)
C10'—C1'—C5—N4	17.7 (8)	O21—C21—O22—C23B	−12.3 (14)
C6'—C1'—C5—N4	−106.9 (7)	C2—C21—O22—C23B	168.7 (12)
C7'—C1'—C5—N4	147.9 (6)	O21—C21—O22—C23	8.6 (10)
C10'—C1'—C5—C3'	−164.0 (6)	C2—C21—O22—C23	−170.4 (7)
C6'—C1'—C5—C3'	71.4 (6)	C21—O22—C23—C24	175.3 (7)
C7'—C1'—C5—C3'	−33.8 (6)	C23B—O22—C23—C24	−50 (4)
C4'—C3'—C5—N4	178.4 (6)	C21—O22—C23B—C24B	96 (3)
C4'—C3'—C5—C1'	0.1 (7)	C23—O22—C23B—C24B	40 (2)
C7'—C4'—C5'—C6'	−36.0 (6)	C2—S1—C111—C116	66.9 (5)
C3'—C4'—C5'—C6'	73.1 (6)	C2—S1—C111—C112	−117.2 (5)
C5—C1'—C6'—C5'	−70.4 (6)	C116—C111—C112—C113	−0.6 (8)
C10'—C1'—C6'—C5'	164.3 (5)	S1—C111—C112—C113	−176.6 (4)
C7'—C1'—C6'—C5'	34.6 (6)	C111—C112—C113—C114	0.6 (9)
C4'—C5'—C6'—C1'	0.1 (7)	C112—C113—C114—C115	0.5 (9)
C5'—C4'—C7'—C8'	173.2 (5)	C112—C113—C114—N1	178.8 (5)
C3'—C4'—C7'—C8'	62.9 (7)	C113—C114—C115—C116	−1.5 (8)
C5'—C4'—C7'—C9'	−62.0 (7)	N1—C114—C115—C116	−179.8 (5)
C3'—C4'—C7'—C9'	−172.3 (6)	C112—C111—C116—C115	−0.5 (9)
C5'—C4'—C7'—C1'	56.2 (5)	S1—C111—C116—C115	175.4 (5)
C3'—C4'—C7'—C1'	−54.1 (6)	C114—C115—C116—C111	1.5 (9)
C5—C1'—C7'—C8'	−64.2 (6)	C113—C114—N1—O2	3.5 (8)
C10'—C1'—C7'—C8'	62.7 (7)	C115—C114—N1—O2	−178.1 (5)
C6'—C1'—C7'—C8'	−171.7 (5)	C113—C114—N1—O1	−174.4 (5)
C5—C1'—C7'—C9'	171.0 (5)	C115—C114—N1—O1	4.0 (7)