6-Deoxy-1,2:3,4-di-O-iso­propyl­idene-α-D-galacto-heptodialdo-1,5-pyran­ose di­phenyl di­thio­acetal

The structure of the title compound, C₂₅H₃₀O₅S₂, was determined by single-crystal X-ray diffraction at 100 K. The bond angles of the di­thia­ne unit as well as the bond lengths of the whole mol­ecule are within the expected ranges.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.107
• Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.702     0.970
            Tmin' and Tmax expected:      0.897     0.969
            RR' =      0.783
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.78
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.15 Ratio

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           28.28
           From the CIF: _reflns_number_total               6099
           Count of symmetry unique reflns         3460
           Completeness (_total/calc)            176.27%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2639
           Fraction of Friedel pairs measured     0.763
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   1 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

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Computing details

Data collection: SMART (Bruker, 1997-2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

6-Deoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-heptodialdo-1,5- pyranose diphenyl dithioacetal

Crystal data

C25H30O5S2	Dx = 1.280 Mg m^−3
Mr = 474.61	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 11023 reflections
a = 9.0880 (4) Å	θ = 2.7–31.7°
b = 10.2194 (5) Å	µ = 0.25 mm^−1
c = 26.5100 (13) Å	T = 100 K
V = 2462.1 (2) Å^3	Block, colourless
Z = 4	0.43 × 0.25 × 0.13 mm
F(000) = 1008

Data collection

Bruker SMART APEX CCD diffractometer	6099 independent reflections
Radiation source: fine-focus sealed tube	6072 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 28.3°, θmin = 1.5°
Absorption correction: multi scan (SADABS in SAINT-Plus; Bruker, 1997-1999)	h = −12→12
Tmin = 0.702, Tmax = 0.97	k = −13→10
29848 measured reflections	l = −35→34

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Only H-atom coordinates refined
wR(F^2) = 0.107	w = 1/[σ^2(Fo^2) + (0.106P)^2 + 0.6861P] where P = (Fo^2 + 2Fc^2)/3
S = 1.37	(Δ/σ)max < 0.001
6099 reflections	Δρmax = 0.40 e Å^−3
347 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Absolute structure: (Flack, 1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (7)

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
C1	0.2855 (2)	0.0913 (2)	0.90422 (8)	0.0162 (4)
C2	0.3619 (2)	0.1739 (2)	0.94474 (8)	0.0156 (4)
C3	0.3155 (2)	0.3162 (2)	0.94497 (9)	0.0170 (4)
C4	0.1481 (2)	0.3371 (2)	0.93886 (8)	0.0160 (4)
C5	0.0691 (2)	0.2135 (2)	0.92124 (8)	0.0155 (4)
C6	−0.0801 (2)	0.2428 (2)	0.89773 (9)	0.0153 (4)
C7	−0.1529 (2)	0.1220 (2)	0.87451 (8)	0.0151 (4)
C8	0.2935 (3)	−0.0212 (2)	0.98137 (8)	0.0181 (4)
C9	0.1698 (3)	−0.0708 (3)	1.01396 (11)	0.0273 (5)
H9A	0.0787	−0.0250	1.0051	0.041*
H9B	0.1932	−0.0547	1.0495	0.041*
H9C	0.1571	−0.1650	1.0085	0.041*
C10	0.4364 (3)	−0.0950 (2)	0.98963 (9)	0.0201 (4)
H10A	0.4686	−0.0836	1.0246	0.030*
H10B	0.5120	−0.0608	0.9668	0.030*
H10C	0.4209	−0.1882	0.9828	0.030*
C11	0.2817 (3)	0.4792 (2)	0.88708 (9)	0.0204 (5)
C12	0.2881 (3)	0.4923 (3)	0.83038 (10)	0.0318 (6)
H12A	0.2233	0.5637	0.8196	0.048*
H12B	0.2557	0.4103	0.8148	0.048*
H12C	0.3893	0.5114	0.8200	0.048*
C13	0.3182 (3)	0.6051 (2)	0.91528 (10)	0.0253 (5)
H13A	0.3118	0.5895	0.9517	0.038*
H13B	0.2480	0.6735	0.9057	0.038*
H13C	0.4182	0.6331	0.9066	0.038*
C21	−0.2175 (3)	−0.1405 (2)	0.89023 (8)	0.0194 (4)
C22	−0.0970 (3)	−0.2232 (3)	0.89085 (10)	0.0263 (5)
C23	−0.1023 (3)	−0.3406 (3)	0.86469 (11)	0.0340 (6)
C24	−0.2251 (4)	−0.3737 (3)	0.83709 (11)	0.0354 (6)
C25	−0.3448 (3)	−0.2901 (3)	0.83609 (12)	0.0336 (6)
C26	−0.3426 (3)	−0.1743 (3)	0.86321 (10)	0.0266 (5)
C31	−0.2557 (3)	0.2568 (2)	0.78830 (9)	0.0197 (5)
C32	−0.3627 (3)	0.3295 (3)	0.76297 (11)	0.0309 (6)
H32	−0.452 (4)	0.325 (4)	0.7744 (13)	0.037*
C33	−0.3231 (4)	0.4058 (4)	0.72231 (13)	0.0458 (9)
H33	−0.393 (4)	0.458 (4)	0.7080 (16)	0.055*
C34	−0.1784 (4)	0.4126 (4)	0.70638 (13)	0.0475 (9)
H34	−0.156 (5)	0.466 (4)	0.6792 (15)	0.057*
C35	−0.0713 (3)	0.3412 (3)	0.73113 (10)	0.0340 (6)
H35	0.027 (4)	0.345 (4)	0.7183 (13)	0.041*
C36	−0.1101 (3)	0.2621 (3)	0.77187 (9)	0.0233 (5)
H36	−0.035 (4)	0.209 (3)	0.7876 (12)	0.028*
H1	0.344 (4)	0.072 (3)	0.8784 (12)	0.028*
H2	0.468 (3)	0.164 (3)	0.9422 (12)	0.028*
H3	0.351 (3)	0.354 (3)	0.9757 (12)	0.028*
H4	0.105 (3)	0.370 (3)	0.9693 (12)	0.028*
H5	0.062 (3)	0.159 (3)	0.9477 (12)	0.028*
H7	−0.084 (3)	0.074 (3)	0.8543 (11)	0.028*
H22	−0.015 (4)	−0.201 (3)	0.9084 (12)	0.028*
H23	−0.025 (4)	−0.398 (3)	0.8649 (11)	0.028*
H24	−0.227 (4)	−0.443 (3)	0.8178 (11)	0.028*
H25	−0.422 (4)	−0.309 (3)	0.8179 (12)	0.028*
H26	−0.425 (4)	−0.119 (3)	0.8636 (11)	0.028*
H6A	−0.065 (3)	0.302 (3)	0.8692 (12)	0.028*
H6B	−0.141 (3)	0.283 (3)	0.9224 (12)	0.028*
O1	0.15783 (17)	0.14869 (15)	0.88402 (6)	0.0159 (3)
O2	0.25195 (18)	−0.02785 (15)	0.92904 (6)	0.0206 (3)
O3	0.31337 (19)	0.11639 (15)	0.99096 (6)	0.0176 (3)
O4	0.37766 (19)	0.37605 (16)	0.90170 (7)	0.0214 (4)
O5	0.13749 (18)	0.43632 (16)	0.90108 (7)	0.0216 (4)
S1	−0.31891 (6)	0.16211 (6)	0.83969 (2)	0.02087 (12)
S2	−0.20971 (6)	0.00966 (6)	0.92426 (2)	0.01927 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0149 (10)	0.0171 (10)	0.0166 (9)	−0.0003 (8)	−0.0001 (8)	−0.0034 (8)
C2	0.0138 (9)	0.0165 (10)	0.0164 (10)	−0.0009 (8)	−0.0014 (8)	−0.0025 (8)
C3	0.0149 (10)	0.0135 (9)	0.0226 (10)	−0.0021 (8)	−0.0014 (8)	−0.0033 (8)
C4	0.0137 (10)	0.0155 (10)	0.0187 (10)	−0.0003 (8)	−0.0007 (7)	−0.0025 (8)
C5	0.0186 (10)	0.0151 (9)	0.0129 (9)	−0.0024 (8)	0.0017 (8)	−0.0006 (8)
C6	0.0150 (10)	0.0135 (10)	0.0174 (10)	−0.0026 (8)	0.0005 (8)	0.0012 (8)
C7	0.0120 (10)	0.0176 (10)	0.0157 (10)	−0.0017 (8)	−0.0011 (8)	0.0037 (8)
C8	0.0185 (10)	0.0157 (10)	0.0202 (10)	−0.0001 (8)	−0.0033 (8)	0.0007 (8)
C9	0.0182 (11)	0.0276 (12)	0.0360 (13)	0.0004 (10)	0.0016 (10)	0.0085 (11)
C10	0.0171 (10)	0.0176 (10)	0.0257 (11)	0.0009 (9)	−0.0024 (9)	0.0009 (9)
C11	0.0200 (11)	0.0161 (10)	0.0251 (11)	−0.0056 (9)	0.0001 (9)	0.0006 (9)
C12	0.0399 (15)	0.0276 (13)	0.0278 (13)	−0.0041 (13)	0.0013 (11)	0.0036 (10)
C13	0.0228 (12)	0.0172 (10)	0.0358 (13)	−0.0039 (9)	−0.0017 (10)	−0.0009 (10)
C21	0.0237 (11)	0.0154 (10)	0.0192 (10)	−0.0041 (9)	0.0004 (9)	0.0041 (8)
C22	0.0254 (13)	0.0291 (13)	0.0242 (12)	0.0008 (10)	−0.0041 (10)	0.0056 (10)
C23	0.0396 (16)	0.0277 (14)	0.0349 (15)	0.0118 (13)	0.0003 (12)	0.0031 (12)
C24	0.0543 (18)	0.0206 (12)	0.0314 (13)	−0.0062 (12)	0.0018 (14)	0.0002 (11)
C25	0.0339 (15)	0.0281 (13)	0.0387 (15)	−0.0106 (12)	−0.0086 (13)	−0.0026 (12)
C26	0.0195 (12)	0.0254 (12)	0.0349 (13)	−0.0040 (10)	−0.0047 (10)	−0.0007 (11)
C31	0.0233 (12)	0.0179 (10)	0.0178 (10)	−0.0042 (9)	−0.0030 (9)	0.0017 (8)
C32	0.0223 (12)	0.0312 (14)	0.0391 (15)	−0.0053 (11)	−0.0095 (11)	0.0136 (12)
C33	0.0394 (17)	0.052 (2)	0.0465 (18)	−0.0069 (16)	−0.0188 (15)	0.0309 (16)
C34	0.0438 (19)	0.060 (2)	0.0391 (16)	−0.0202 (18)	−0.0137 (15)	0.0305 (16)
C35	0.0335 (14)	0.0457 (17)	0.0228 (12)	−0.0079 (14)	0.0003 (11)	0.0086 (12)
C36	0.0266 (13)	0.0266 (13)	0.0167 (11)	−0.0013 (10)	−0.0002 (9)	0.0027 (10)
O1	0.0154 (7)	0.0170 (7)	0.0154 (7)	0.0011 (6)	−0.0005 (6)	−0.0039 (6)
O2	0.0244 (8)	0.0148 (7)	0.0226 (8)	−0.0012 (6)	−0.0076 (7)	−0.0019 (6)
O3	0.0199 (8)	0.0157 (7)	0.0173 (7)	0.0005 (6)	−0.0001 (6)	−0.0016 (6)
O4	0.0192 (8)	0.0173 (8)	0.0276 (9)	−0.0021 (6)	0.0024 (7)	0.0021 (7)
O5	0.0170 (8)	0.0172 (8)	0.0307 (9)	−0.0020 (6)	−0.0038 (7)	0.0075 (7)
S1	0.0135 (2)	0.0267 (3)	0.0224 (3)	−0.0034 (2)	−0.0019 (2)	0.0063 (2)
S2	0.0215 (3)	0.0197 (3)	0.0166 (2)	−0.0055 (2)	0.0011 (2)	0.0025 (2)

Geometric parameters (Å, º)

C1—O1	1.406 (3)	C11—O5	1.431 (3)
C1—O2	1.417 (3)	C11—C12	1.510 (3)
C1—C2	1.533 (3)	C11—C13	1.524 (3)
C1—H1	0.89 (3)	C12—H12A	0.9800
C2—O3	1.429 (3)	C12—H12B	0.9800
C2—C3	1.515 (3)	C12—H12C	0.9800
C2—H2	0.97 (3)	C13—H13A	0.9800
C3—O4	1.417 (3)	C13—H13B	0.9800
C3—C4	1.545 (3)	C13—H13C	0.9800
C3—H3	0.96 (3)	C21—C22	1.383 (4)
C4—O5	1.428 (3)	C21—C26	1.387 (3)
C4—C5	1.526 (3)	C21—S2	1.782 (2)
C4—H4	0.96 (3)	C22—C23	1.387 (4)
C5—O1	1.436 (3)	C22—H22	0.91 (3)
C5—C6	1.522 (3)	C23—C24	1.376 (4)
C5—H5	0.90 (3)	C23—H23	0.91 (3)
C6—C7	1.530 (3)	C24—C25	1.383 (5)
C6—H6A	0.98 (3)	C24—H24	0.87 (3)
C6—H6B	0.95 (3)	C25—C26	1.385 (4)
C7—S1	1.816 (2)	C25—H25	0.87 (3)
C7—S2	1.823 (2)	C26—H26	0.94 (3)
C7—H7	0.96 (3)	C31—C36	1.394 (4)
C8—O2	1.439 (3)	C31—C32	1.396 (3)
C8—O3	1.441 (3)	C31—S1	1.767 (2)
C8—C9	1.506 (3)	C32—C33	1.378 (4)
C8—C10	1.517 (3)	C32—H32	0.87 (4)
C9—H9A	0.9800	C33—C34	1.383 (5)
C9—H9B	0.9800	C33—H33	0.91 (4)
C9—H9C	0.9800	C34—C35	1.382 (5)
C10—H10A	0.9800	C34—H34	0.93 (4)
C10—H10B	0.9800	C35—C36	1.394 (4)
C10—H10C	0.9800	C35—H35	0.96 (4)
C11—O4	1.423 (3)	C36—H36	0.97 (3)
O1—C1—O2	110.96 (18)	O4—C11—C12	108.3 (2)
O1—C1—C2	114.27 (18)	O5—C11—C12	108.7 (2)
O2—C1—C2	104.20 (17)	O4—C11—C13	110.99 (19)
O1—C1—H1	107 (2)	O5—C11—C13	109.3 (2)
O2—C1—H1	107 (2)	C12—C11—C13	113.9 (2)
C2—C1—H1	113 (2)	C11—C12—H12A	109.5
O3—C2—C3	107.78 (18)	C11—C12—H12B	109.5
O3—C2—C1	103.57 (17)	H12A—C12—H12B	109.5
C3—C2—C1	113.92 (18)	C11—C12—H12C	109.5
O3—C2—H2	108.7 (19)	H12A—C12—H12C	109.5
C3—C2—H2	112 (2)	H12B—C12—H12C	109.5
C1—C2—H2	110.1 (19)	C11—C13—H13A	109.5
O4—C3—C2	107.45 (18)	C11—C13—H13B	109.5
O4—C3—C4	104.37 (18)	H13A—C13—H13B	109.5
C2—C3—C4	114.01 (18)	C11—C13—H13C	109.5
O4—C3—H3	112.3 (19)	H13A—C13—H13C	109.5
C2—C3—H3	107.2 (19)	H13B—C13—H13C	109.5
C4—C3—H3	111.6 (19)	C22—C21—C26	120.2 (2)
O5—C4—C5	109.96 (18)	C22—C21—S2	119.26 (19)
O5—C4—C3	103.77 (17)	C26—C21—S2	120.6 (2)
C5—C4—C3	112.36 (19)	C21—C22—C23	119.7 (3)
O5—C4—H4	108.4 (19)	C21—C22—H22	120 (2)
C5—C4—H4	111 (2)	C23—C22—H22	120 (2)
C3—C4—H4	111.2 (18)	C24—C23—C22	120.4 (3)
O1—C5—C6	108.02 (18)	C24—C23—H23	118 (2)
O1—C5—C4	109.17 (18)	C22—C23—H23	122 (2)
C6—C5—C4	112.42 (19)	C23—C24—C25	119.7 (3)
O1—C5—H5	107 (2)	C23—C24—H24	122 (2)
C6—C5—H5	112 (2)	C25—C24—H24	118 (2)
C4—C5—H5	108 (2)	C24—C25—C26	120.4 (3)
C5—C6—C7	113.05 (19)	C24—C25—H25	120 (2)
C5—C6—H6A	108.4 (19)	C26—C25—H25	119 (2)
C7—C6—H6A	104.3 (19)	C25—C26—C21	119.5 (3)
C5—C6—H6B	108.7 (19)	C25—C26—H26	120 (2)
C7—C6—H6B	112 (2)	C21—C26—H26	120 (2)
H6A—C6—H6B	111 (3)	C36—C31—C32	119.3 (2)
C6—C7—S1	112.44 (16)	C36—C31—S1	124.82 (19)
C6—C7—S2	109.84 (15)	C32—C31—S1	115.8 (2)
S1—C7—S2	105.94 (11)	C33—C32—C31	119.7 (3)
C6—C7—H7	110.6 (19)	C33—C32—H32	123 (2)
S1—C7—H7	112.0 (18)	C31—C32—H32	117 (2)
S2—C7—H7	105.6 (19)	C32—C33—C34	121.0 (3)
O2—C8—O3	104.41 (16)	C32—C33—H33	118 (3)
O2—C8—C9	109.96 (19)	C34—C33—H33	120 (3)
O3—C8—C9	108.70 (19)	C35—C34—C33	119.9 (3)
O2—C8—C10	109.90 (19)	C35—C34—H34	122 (3)
O3—C8—C10	110.61 (18)	C33—C34—H34	119 (3)
C9—C8—C10	112.90 (19)	C34—C35—C36	119.7 (3)
C8—C9—H9A	109.5	C34—C35—H35	118 (2)
C8—C9—H9B	109.5	C36—C35—H35	122 (2)
H9A—C9—H9B	109.5	C31—C36—C35	120.3 (3)
C8—C9—H9C	109.5	C31—C36—H36	120.8 (19)
H9A—C9—H9C	109.5	C35—C36—H36	119 (2)
H9B—C9—H9C	109.5	C1—O1—C5	113.20 (16)
C8—C10—H10A	109.5	C1—O2—C8	110.53 (16)
C8—C10—H10B	109.5	C2—O3—C8	106.79 (16)
H10A—C10—H10B	109.5	C3—O4—C11	107.20 (17)
C8—C10—H10C	109.5	C4—O5—C11	109.75 (16)
H10A—C10—H10C	109.5	C31—S1—C7	104.20 (11)
H10B—C10—H10C	109.5	C21—S2—C7	100.79 (10)
O4—C11—O5	105.29 (17)