Structure k85d		
Sample BC - pHP - FOR	

Crystal Structure Report 

for 

C9H8O4

Professor Rich Givens

Beth Cope 

January 28, 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 C9H8O4 molecule.  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 C9H8O4 are, at 100(2) K, monoclinic, space group P21/c – C2h5 (No. 14) (1) with a = 8.9605(6) Å, b = 8.3220(6) Å, c = 10.6750(7) Å,  = 98.930(2), V = 786.38(9) Å3 and Z =  4 molecules {dcalcd = 1.522 g/cm3; a(MoK) = 0.121 mm-1}.   A full hemisphere of diffracted intensities (1850 10-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 30mA.  Lattice constants were determined with the Bruker SAINT software package using peak centers for 3517 reflections.  A total of 9794 integrated reflection intensities having 2((MoK)< 60.99 were produced using the Bruker program SAINT(3); 2389 of these were unique and gave Rint = 0.033 with a coverage which was 99.7% complete. The data were corrected empirically for variable absorption effects using equivalent reflections; the relative transmission factors ranged from 0.949 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 150 parameters were refined using no restraints, 2389 data and weights of w = 1/ [2(F2) + (0.0721 P)2], where P = [Fo2 + 2Fc2] / 3.  Final agreement factors at convergence are:  R1(unweighted, based on F) = 0.039 for 1979 independent absorption-corrected “observed” reflections having 2(MoK)<  60.99 and I>2(I);  R1(unweighted, based on F) = 0.046 and wR2(weighted, based on F2) = 0.107 for all 2389 independent absorption-corrected reflections having 2(MoK)< 60.99.  The largest shift/s.u. was 0.000 in the final refinement cycle.  The final difference map had maxima and minima of 0.47 and 
-0.24 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 C9H8O4.
Empirical formula 	C9H8O4
Formula weight 	180.15
Temperature 	100(2) K
Wavelength 	0.71073 Å
Crystal system 	Monoclinic
Space group 	P21/c – C2h5 (No. 14)
Unit cell dimensions	a = 8.9605(6) Å	α = 90.000°
	b = 8.3220(6) Å	β = 98.930(2)°.
	c = 10.6750(7) Å	γ = 90.000°
Volume	786.38(9) Å3
Z	4
Density (calculated)	1.522 Mg/m3
Absorption coefficient	0.121 mm-1
F(000)	376
Crystal size	0.40 x 0.21 x 0.10 mm3
Theta range for data collection	2.30° to 30.50°
Index ranges	-12 ≤ h ≤ 12, -11 ≤ k ≤ 11, -15 ≤ l ≤ 14
Reflections collected	9794
Independent reflections	2389 [Rint = 0.033]
Completeness to theta = 30.50°	99.7 % 
Absorption correction	Multi-scan
Max. and min. transmission	1.000 and 0.949
Refinement method	Full-matrix least-squares on F2
Data / restraints / parameters	2389 / 0 / 150
Goodness-of-fit on F2	0.988
Final R indices [I>2sigma(I)]	R1 = 0.039, wR2 = 0.104
R indices (all data)	R1 = 0.046, wR2 = 0.107
Largest diff. peak and hole	0.47 and -0.24 e-/Å3

Table 2.  Atomic coordinates  ( x 104) and equivalent  isotropic displacement parameters (Å2 x 103)
for C9H8O4. U(eq) is defined as one third of  the trace of the orthogonalized Uij tensor.
________________________________________________________________________________ 
	x	y	z	U(eq)
________________________________________________________________________________  
O(1)	3891(1)	1256(1)	4042(1)	25(1)
O(2)	5118(1)	1673(1)	2383(1)	25(1)
O(3)	2168(1)	2019(1)	5676(1)	24(1)
O(4)	899(1)	9365(1)	6434(1)	24(1)
C(1)	4719(1)	812(1)	3159(1)	23(1)
C(2)	3482(1)	2925(1)	4037(1)	19(1)
C(3)	2554(1)	3173(1)	5095(1)	17(1)
C(4)	2150(1)	4822(1)	5396(1)	16(1)
C(5)	1342(1)	5058(1)	6410(1)	17(1)
C(6)	935(1)	6576(1)	6741(1)	18(1)
C(7)	1325(1)	7902(1)	6061(1)	17(1)
C(8)	2112(1)	7697(1)	5045(1)	18(1)
C(9)	2519(1)	6168(1)	4717(1)	17(1)
________________________________________________________________________________ 
Table 3.   Bond lengths [Å] for C9H8O4.
________________________________________________________________________________ 
O(1)-C(1) 	1.339(1)
O(1)-C(2) 	1.437(1)
O(2)-C(1) 	1.192(1)
O(3)-C(3) 	1.222(1)
O(4)-C(7) 	1.354(1)
O(4)-H(4O) 	0.83(2)
C(1)-H(1) 	0.98(1)
C(2)-C(3) 	1.517(1)
C(2)-H(2A) 	0.98(1)
C(2)-H(2B) 	0.98(1)
C(3)-C(4) 	1.468(1)
C(4)-C(9) 	1.401(1)
C(4)-C(5) 	1.406(1)
C(5)-C(6) 	1.377(1)
C(5)-H(5) 	0.97(1)
C(6)-C(7) 	1.395(1)
C(6)-H(6) 	1.00(2)
C(7)-C(8) 	1.393(1)
C(8)-C(9) 	1.384(1)
C(8)-H(8) 	0.96(1)
C(9)-H(9) 	0.97(1)
________________________________________________________________________________ 

Table 4.   Bond angles [°] for  C9H8O4.
__________________________________________________________________________

C(1)-O(1)-C(2)	115.7(1)
C(7)-O(4)-H(4O)	108(1)
O(2)-C(1)-O(1)	125.7(1)
O(2)-C(1)-H(1)	126(1)
O(1)-C(1)-H(1)	108(1)
O(1)-C(2)-C(3)	107.3(1)
O(1)-C(2)-H(2A)	110(1)
C(3)-C(2)-H(2A)	111(1)
O(1)-C(2)-H(2B)	110(1)
C(3)-C(2)-H(2B)	111(1)
H(2A)-C(2)-H(2B)	109(1)
O(3)-C(3)-C(4)	121.7(1)
O(3)-C(3)-C(2)	120.1(1)
C(4)-C(3)-C(2)	118.2(1)
C(9)-C(4)-C(5)	118.6(1)
C(9)-C(4)-C(3)	123.2(1)
C(5)-C(4)-C(3)	118.2(1)
C(6)-C(5)-C(4)	120.9(1)
C(6)-C(5)-H(5)	120(1)
C(4)-C(5)-H(5)	119(1)
C(5)-C(6)-C(7)	119.6(1)
C(5)-C(6)-H(6)	121(1)
C(7)-C(6)-H(6)	120(1)
O(4)-C(7)-C(8)	122.6(1)
O(4)-C(7)-C(6)	116.9(1)
C(8)-C(7)-C(6)	120.5(1)
C(9)-C(8)-C(7)	119.6(1)
C(9)-C(8)-H(8)	120(1)
C(7)-C(8)-H(8)	120(1)
C(8)-C(9)-C(4)	120.8(1)
C(8)-C(9)-H(9)	120(1)
C(4)-C(9)-H(9)	119(1)

________________________________________________________________________________

Table 5.   Anisotropic displacement parameters  (Å2 x 103) for C9H8O4. The anisotropic
displacement factor exponent takes the form:  -22[ h2 a*2U11 + ...  + 2 h k a* b* U12 ]
______________________________________________________________________________ 
	U11	U22	U33	U23	U13	U12
______________________________________________________________________________ 
O(1)	35(1) 	15(1)	27(1) 	1(1)	14(1) 	5(1)
O(2)	26(1) 	25(1)	25(1) 	-2(1)	9(1) 	0(1)
O(3)	30(1) 	15(1)	28(1) 	2(1)	10(1) 	-2(1)
O(4)	35(1) 	12(1)	27(1) 	0(1)	15(1) 	0(1)
C(1)	26(1) 	20(1)	25(1) 	-3(1)	6(1) 	3(1)
C(2)	24(1) 	13(1)	22(1) 	-1(1)	7(1) 	2(1)
C(3)	17(1) 	15(1)	18(1) 	-1(1)	2(1) 	-1(1)
C(4)	17(1) 	15(1)	17(1) 	0(1)	3(1) 	-2(1)
C(5)	18(1) 	15(1)	18(1) 	3(1)	4(1) 	-2(1)
C(6)	20(1) 	17(1)	18(1) 	0(1)	6(1) 	-1(1)
C(7)	20(1) 	14(1)	19(1) 	0(1)	4(1) 	-1(1)
C(8)	21(1) 	15(1)	18(1) 	2(1)	5(1) 	-3(1)
C(9)	19(1) 	17(1)	17(1) 	1(1)	5(1) 	-1(1)
______________________________________________________________________________ 
Table 6.   Hydrogen coordinates ( x 104) and isotropic  displacement parameters (Å2 x 103)
for C9H8O4.
________________________________________________________________________________ 
	x 	y 	z 	U(eq)
________________________________________________________________________________ 
 H(4O)	1278(17)	10059(19)	6021(15)	40(4)
H(1)	4906(14)	-351(17)	3247(12)	24(3)
H(2A)	4402(15)	3589(15)	4164(13)	25(3)
H(2B)	2892(14)	3201(14)	3219(13)	19(3)
H(5)	1070(13)	4131(16)	6870(11)	22(3)
H(6)	354(17)	6740(17)	7461(15)	32(4)
H(8)	2385(15)	8615(17)	4587(13)	30(4)
H(9)	3018(15)	6005(17)	3988(13)	29(3)
________________________________________________________________________________ 
Table 7.  Torsion angles [°] for C9H8O4.
________________________________________________________________________________ C(2)-O(1)-C(1)-O(2)	-0.78(16)
C(1)-O(1)-C(2)-C(3)	179.89(9)
O(1)-C(2)-C(3)-O(3)	-7.16(13)
O(1)-C(2)-C(3)-C(4)	172.58(8)
O(3)-C(3)-C(4)-C(9)	-177.27(9)
C(2)-C(3)-C(4)-C(9)	3.00(14)
O(3)-C(3)-C(4)-C(5)	2.21(14)
C(2)-C(3)-C(4)-C(5)	-177.52(8)
C(9)-C(4)-C(5)-C(6)	-0.73(14)
C(3)-C(4)-C(5)-C(6)	179.77(9)
C(4)-C(5)-C(6)-C(7)	0.15(15)
C(5)-C(6)-C(7)-O(4)	-179.74(9)
C(5)-C(6)-C(7)-C(8)	0.50(15)
O(4)-C(7)-C(8)-C(9)	179.69(9)
C(6)-C(7)-C(8)-C(9)	-0.56(15)
C(7)-C(8)-C(9)-C(4)	-0.03(14)
C(5)-C(4)-C(9)-C(8)	0.66(14)
C(3)-C(4)-C(9)-C(8)	-179.87(9)
________________________________________________________________________________

Table 8.  Hydrogen bonds for C9H8O4  [Å and °].
____________________________________________________________________________ 
D-H...A	d(D-H)	d(H...A)	d(D...A)	<(DHA)
____________________________________________________________________________ 
 O(4)-H(4O)...O(3)#1	0.830(17)	1.877(16)	2.6671(11)	158.5(16)
____________________________________________________________________________ 
Symmetry transformations used to generate equivalent atoms:  #1:  x, y+1, z.