Structure 48d		
Sample BC-pHP-Mes		

Crystal Structure Report 

for 

C9H10O5S

Professor Rich Givens

Beth Cope 

January 24, 2008

 Contents 
	
Figure 1.  50% Probability Ellipsoid Drawing of Molecule ... …....    3
Figure 2.  Packing Diagram ..........................................……….…	12
Comments .............................................................…………….…	15
Experimental .........................................................……………….	15
Acknowledgements .....................................................…………..	16
References ...........................................................………………..	16
Table 1.  Crystal Data ...............................................…………….	17
Table 2.  Atom Coordinates for Nonhydrogen Atoms......………… 18
Table 3.  Bond Lengths ……………….................................…..….	19
Table 4.  Bond Angles …………………................................…….. 	20
Table 5.  Nonhydrogen Anisotropic Displacement Parameters ..   21
Table 6.  Hydrogen Atom Parameters .................................…....	 22
Table 7.  Torsion Angles .............................................…….…….	 23
Table 8.  Hydrogen Bond Geometries .................................…….	 24

Appendix: 
Table 9.  Structure Factors ..........................................…………..	 1

Comments
	The asymmetric unit contains one half of a C9H10O5S molecule.  All but one nonhydrogen atom and two hydrogen atoms of the molecule lie in the crystallographic mirror plane at y = 0.25 in the unit cell.  All displacement ellipsoids are drawn at the 50% probability level.

Brief  Experimental Description to be Included as Text or as a Footnote at Time of Publication
	 Colorless crystals of C9H10O5S are, at 100(2) K, monoclinic, space group P21/m - C2h2 (No. 11) (1) with a = 8.129(1) Å, b = 6.609(1) Å, c = 8.868(1) Å,  = 97.535(3), V = 472.3(1) Å3 and Z = 2 molecules {dcalcd = 1.619 g/cm3; a(MoK) = 0.341 mm-1}.   A full hemisphere of diffracted intensities (1850 20-second frames with a  scan width of 0.30) was measured for a single-domain specimen using graphite-monochromated MoK radiation (= 0.71073 Å) on a Bruker SMART APEX CCD Single Crystal Diffraction System (2).  X-rays were provided by a fine-focus sealed x-ray tube operated at 50kV and 35mA.  Lattice constants were determined with the Bruker SAINT software package using peak centers for 2085 reflections.  A total of 5835 integrated reflection intensities having 2((MoK)< 60.95 were produced using the Bruker program SAINT(3); 1551 of these were unique and gave Rint = 0.038 with a coverage which was 99.6% complete. The data were corrected empirically for variable absorption effects using  equivalent reflections; the relative transmission factors ranged from 0.934 to 1.000.  The Bruker software package SHELXTL was used to solve the structure using “direct methods” techniques.  All stages of weighted full-matrix least-squares refinement were conducted using Fo2 data with the SHELXTL Version 6.10 software package(4). 
	The final structural model incorporated anisotropic thermal parameters for all nonhydrogen atoms and isotropic thermal parameters for all hydrogen atoms.  All hydrogen atoms were located in a difference Fourier and included in the structural model as independent isotropic atoms whose parameters were allowed to vary in least-squares refinement cycles.  A total of 114 parameters were refined using no restraints, 1551 data and weights of w = 1/ [2(F2) + (0.0573 P)2], where P = [Fo2 + 2Fc2] / 3.  Final agreement factors at convergence are:  R1(unweighted, based on F) = 0.042 for 1383 independent absorption-corrected “observed” reflections having 2(MoK)<  60.95 and I>2(I);  R1(unweighted, based on F) = 0.049 and wR2(weighted, based on F2) = 0.106 for all 1551 independent absorption-corrected reflections having 2(MoK)< 60.95.  The largest shift/s.u. was 0.000 in the final refinement cycle.  The final difference map had maxima and minima of 0.74 and 
-0.27 e-/Å3, respectively.  

   
 Acknowledgment
	The authors thank the National Science Foundation (grant CHE-0079282) and the University of Kansas for funds to purchase the  x-ray instrument and computers.  

References

(1)	 International Tables for Crystallography, Vol A, 4th ed., Kluwer:  Boston (1996). 
(2)	Data Collection:  SMART Software Reference Manual (1998). Bruker-AXS, 5465 E. Cheryl Parkway, Madison, WI  53711-5373  USA.   
(3)	Data Reduction:  SAINT Software Reference Manual (1998). Bruker-AXS, 6300 Enterprise Dr., Madison, WI 53719-1173, USA. 
(4)	G. M. Sheldrick (2000). SHELXTL Version 6.10 Reference Manual. Bruker-AXS, 5465 E. Cheryl Parkway, Madison, WI  53711-5373 USA.  

Table 1.  Crystal data and structure refinement for C9H10O5S.
Empirical formula 	C9H10O5S
Formula weight 	230.23
Temperature 	100(2) K
Wavelength 	0.71073 Å
Crystal system 	Monoclinic
Space group 	P21/m - C2h2 (No. 11)
Unit cell dimensions	a = 8.129(1) Å	α = 90.000°
	b = 6.609(1) Å	β = 97.535(3)°.
	c = 8.868(1) Å	γ = 90.000°
Volume	472.3(1) Å3
Z	2
Density (calculated)	1.619 Mg/m3
Absorption coefficient	0.341 mm-1
F(000)	240
Crystal size	0.15 x 0.13 x 0.04 mm3
Theta range for data collection	2.32° to 30.47°
Index ranges	-11 ≤ h ≤ 11, -9 ≤ k ≤ 9, -12 ≤ l ≤ 12
Reflections collected	5835
Independent reflections	1551 [Rint = 0.038]
Completeness to theta = 30.47°	99.6 % 
Absorption correction	Multi-scans
Max. and min. transmission	1.000 and 0.934
Refinement method	Full-matrix least-squares on F2
Data / restraints / parameters	1551 / 0 / 114
Goodness-of-fit on F2	1.136
Final R indices [I>2sigma(I)]	R1 = 0.042, wR2 = 0.102
R indices (all data)	R1 = 0.049, wR2 = 0.106
Largest diff. peak and hole	0.74 and -0.28 e-/Å3
________________________________________________________________________________
R1 =  ||Fo| - |Fc|| /  |Fo| 
wR2 = {  [w(Fo2 - Fc2)2] /  [w(Fo2)2] }1/2 

Table 2.  Atomic coordinates  ( x 104) and equivalent  isotropic displacement parameters (Å2 x 103)
for C9H10O5S.  U(eq) is defined as one third of  the trace of the orthogonalized Uij tensor.
________________________________________________________________________________ 
	x	y	z	U(eq)
________________________________________________________________________________  
S	2358(1)	2500	4680(1)	11(1)
O(1)	2633(2)	2500	2957(2)	14(1)
O(2)	2817(2)	2500	117(2)	15(1)
O(3)	2964(1)	651(2)	5385(1)	18(1)
O(4)	9979(2)	2500	-1952(2)	19(1)
C(1)	4321(2)	2500	2605(2)	12(1)
C(2)	4183(2)	2500	880(2)	11(1)
C(3)	5735(2)	2500	189(2)	11(1)
C(4)	5646(3)	2500	-1400(2)	12(1)
C(5)	7066(3)	2500	-2099(2)	13(1)
C(6)	8621(2)	2500	-1206(2)	13(1)
C(7)	8732(3)	2500	374(2)	16(1)
C(8)	7296(3)	2500	1063(2)	14(1)
C(9)	196(3)	2500	4362(2)	15(1)
________________________________________________________________________________ 
 Table 3.   Bond lengths [Å] for  C9H10O5S.
________________________________________________________________________________
S-O(3)#1 	1.430(1)
S-O(3) 	1.430(1)
S-O(1) 	1.573(2)
S-C(9) 	1.743(2)
O(1)-C(1) 	1.446(2)
O(2)-C(2) 	1.222(2)
O(4)-C(6) 	1.359(2)
O(4)-H(4O) 	0.69(3)
C(1)-C(2) 	1.519(3)
C(1)-H(1) 	0.93(2)
C(2)-C(3) 	1.473(3)
C(3)-C(8) 	1.398(3)
C(3)-C(4) 	1.401(3)
C(4)-C(5) 	1.379(3)
C(4)-H(4) 	0.92(3)
C(5)-C(6) 	1.401(3)
C(5)-H(5) 	0.95(3)
C(6)-C(7) 	1.392(3)
C(7)-C(8) 	1.386(3)
C(7)-H(7) 	0.85(3)
C(8)-H(8) 	1.00(3)
C(9)-H(9A) 	0.97(3)
C(9)-H(9B) 	0.97(2)
__________________________________________________________________________

Table 4.   Bond angles [°] for  C9H10O5S.
__________________________________________________________________________

O(3)#1-S-O(3)	117.3(1)
O(3)#1-S-O(1)	109.9(1)
O(3)-S-O(1)	109.9(1)
O(3)#1-S-C(9)	110.6(1)
O(3)-S-C(9)	110.6(1)
O(1)-S-C(9)	96.4(1)
C(1)-O(1)-S	118.0(1)
C(6)-O(4)-H(4O)	106(3)
O(1)-C(1)-C(2)	105.7(2)
O(1)-C(1)-H(1)	111(1)
C(2)-C(1)-H(1)	110(1)
O(2)-C(2)-C(3)	122.3(2)
O(2)-C(2)-C(1)	120.0(2)
C(3)-C(2)-C(1)	117.7(2)
C(8)-C(3)-C(4)	118.7(2)
C(8)-C(3)-C(2)	122.3(2)
C(4)-C(3)-C(2)	119.0(2)
C(5)-C(4)-C(3)	121.1(2)
C(5)-C(4)-H(4)	116(2)
C(3)-C(4)-H(4)	122(2)
C(4)-C(5)-C(6)	119.5(2)
C(4)-C(5)-H(5)	123(2)
C(6)-C(5)-H(5)	118(2)
O(4)-C(6)-C(7)	122.7(2)
O(4)-C(6)-C(5)	117.1(2)
C(7)-C(6)-C(5)	120.2(2)
C(8)-C(7)-C(6)	119.8(2)
C(8)-C(7)-H(7)	120(2)
C(6)-C(7)-H(7)	120(2)
C(7)-C(8)-C(3)	120.7(2)
C(7)-C(8)-H(8)	116(2)
C(3)-C(8)-H(8)	123(2)
S-C(9)-H(9A)	106(2)
S-C(9)-H(9B)	110(1)
H(9A)-C(9)-H(9B)	110(1)
__________________________________________________________________________

Symmetry transformations used to generate equivalent atoms:  #1:  x; -y+1/2; z.      

 Table 5.   Anisotropic displacement parameters  (Å2 x 103) for C9H10O5S.  The anisotropic
displacement factor exponent takes the form:  -22[ h2 a*2U11 + ...  + 2 h k a* b* U12 ]
______________________________________________________________________________ 
	U11	U22 	U33	U23	U13	U12
______________________________________________________________________________ 
S	9(1) 	15(1)	10(1) 	0	1(1) 	0
O(1)	9(1) 	25(1)	10(1) 	0	3(1) 	0
O(2)	10(1) 	20(1)	14(1) 	0	0(1) 	0
O(3)	16(1) 	20(1)	18(1) 	4(1)	-1(1) 	3(1)
O(4)	9(1) 	37(1)	12(1) 	0	2(1) 	0
C(1)	9(1) 	14(1)	13(1) 	0	3(1) 	0
C(2)	10(1) 	10(1)	14(1) 	0	1(1) 	0
C(3)	10(1) 	12(1)	12(1) 	0	1(1) 	0
C(4)	9(1) 	13(1)	13(1) 	0	-1(1) 	0
C(5)	13(1) 	17(1)	8(1) 	0	1(1) 	0
C(6)	11(1) 	16(1)	13(1) 	0	3(1) 	0
C(7)	10(1) 	25(1)	11(1) 	0	-1(1) 	0
C(8)	12(1) 	20(1)	10(1) 	0	1(1) 	0
C(9)	11(1) 	20(1)	15(1) 	0	2(1) 	0
______________________________________________________________________________ 
 Table 6.   Hydrogen coordinates ( x 104) and isotropic  displacement parameters (Å2 x 103 )
for C9H10O5S.
________________________________________________________________________________ 
	x 	y 	z 	U(eq)
________________________________________________________________________________ 
 
H(4O)	10660(40)	2500	-1400(30)	29(9)
H(1)	4890(20)	1360(30)	3000(20)	19(5)
H(4)	4650(40)	2500	-2030(40)	41(9)
H(5)	7040(30)	2500	-3180(30)	18(7)
H(7)	9680(40)	2500	920(30)	33(8)
H(8)	7460(30)	2500	2200(30)	27(8)
H(9A)	-170(30)	2500	5360(30)	22(7)
H(9B)	-200(20)	1300(30)	3810(20)	22(5)
________________________________________________________________________________ 
 Table 7.  Torsion angles [°] for C9H10O5S.
________________________________________________________________ 
O(3)#1-S-O(1)-C(1)	65.29(6)
O(3)-S-O(1)-C(1)	-65.29(6)
C(9)-S-O(1)-C(1)	180.0
S-O(1)-C(1)-C(2)	180.0
O(1)-C(1)-C(2)-O(2)	0.0
O(1)-C(1)-C(2)-C(3)	180.0
O(2)-C(2)-C(3)-C(8)	180.0
C(1)-C(2)-C(3)-C(8)	0.0
O(2)-C(2)-C(3)-C(4)	0.0
C(1)-C(2)-C(3)-C(4)	180.0
C(8)-C(3)-C(4)-C(5)	0.0
C(2)-C(3)-C(4)-C(5)	180.0
C(3)-C(4)-C(5)-C(6)	0.0
C(4)-C(5)-C(6)-O(4)	180.0
C(4)-C(5)-C(6)-C(7)	0.0
O(4)-C(6)-C(7)-C(8)	180.0
C(5)-C(6)-C(7)-C(8)	0.0
C(6)-C(7)-C(8)-C(3)	0.0
C(4)-C(3)-C(8)-C(7)	0.0
C(2)-C(3)-C(8)-C(7)	180.0
________________________________________________________________ 
Symmetry transformations used to generate equivalent atoms:  #1:  x; -y+1/2; z.      

 Table 8.  Hydrogen bonds for C9H10O5S  [Å and °].
____________________________________________________________________________ 
D-H...A	d(D-H)	d(H...A)	d(D...A)	<(DHA)
____________________________________________________________________________ 
 O(4)-H(4O)...O(2)#2	0.69(3)	2.07(3)	2.753(2)	175(4)
____________________________________________________________________________ 
Symmetry transformations used to generate equivalent atoms:  #1:  x; -y+1/2; z;  #2:  x+1; y; z.