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Crystal Structure Information for UM # 1255

Prepared by: Peter Y. Zavalij   Feb. 25, 2006

 

Crystal No. & ID

:

1255: M.M. Sugar

Compound name

:

Sucrose

Chemical formula

:

C12H22O11

Final R1 [I>2s(I)]

:

2.43%

 

 

Figure 1.  A view of sugar showing the numbering scheme employed. Anisotropic atomic displacement ellipsoids for the non-hydrogen atoms are shown at the 30% probability level. Hydrogen atoms are displayed with an arbitrarily small radius.

 

 

       A colorless prism of C12H22O11, approximate dimensions 0.38 ´ 0.40 ´ 0.42 mm3, was used for the X-ray crystallographic analysis. The X-ray intensity data were measured at 223(2) K on a three-circle diffractometer system equipped with Bruker Smart1000 CCD area detector using a graphite monochromator and a MoKa fine-focus sealed tube (l= 0.71073 Å) operated at 20 kV and 5 mA. The detector was placed at a distance of 4.99 cm from the crystal.

A total of 1150 frames were collected with a scan width of 0.5° in w and an exposure time of 8 sec/frame using SMART (Bruker, 1999). The total data collection time was 4.8 hours. The frames were integrated with SAINT software package using a narrow-frame integration algorithm. The integration of the data using a Monoclinic unit cell yielded a total of 6859 reflections to a maximum q angle of 27.98°, of which 3324 were independent (completeness = 99.3%, Rint = 1.52%, Rsig = 1.76%) and 3274 were greater than 2s(I). The final cell dimensions of a = 7.7441(5) Å, b = 8.6932(6) Å, c = 10.8537(7) Å, a= 90°, b= 102.9300(10, g= 90°, V = 712.16(8) Å3, are based upon the refinement of the XYZ-centroids of 5971 reflections with 2.7 < q < 29.1° using SAINT. Analysis of the data showed -0.27 % decay during data collection. Data were corrected for absorption effects with the Semi-empirical from equivalents method using SADABS (Sheldrick, 1996). The minimum and maximum transmission coefficients were 0.875 and 0.947.

The structure was solved and refined using the SHELXS-97 (Sheldrick, 1990) and SHELXL-97 (Sheldrick, 1997) software in the space group P21 with Z = 2 for the formula unit C12H22O11. The final anisotropic full-matrix least-squares refinement on F2 with 276 variables converged at R1 = 2.43 % for the observed data and wR2 = 5.33 % for all data. The goodness-of-fit was 1.000. The largest peak on the final difference map was 0.282 ē/Å3 and the largest hole was -0.152 ē/Å3. On the basis of the final model, the calculated density was 1.596 g/cm3 and F(000), 364 ē.

 

Overall structure quality considerations:

1.  Strong data set, no disorder, R1 4% maximum. Publishable quality.

2.  Good data set, perhaps some minor disorder, R1 6% maximum. Publishable quality.

3.  Average data set and/or easily modelled disorder or twinning. Publishable with care.

4.  Weak data and/or major disorder or twinning that is not easily modelled. Publishable in some cases.

5.  Very weak data and/or unexplained features of data or model. Not of publishable quality.

A structure with a quality factor of 4 or 5 should not be used for a regulatory document without prior consultation.

 

 

 Comments:

Data set quality

:

 very good

Twinning

:

 none

Disorder

:

 none

H-atoms refinement

:

 coordinates but not Uiso constrained

Residual density

:

 at the middle of bonds

Structure quality

:

 excellent

Check CIF

:

 Platon

Publishable

:

 No, known structure.

 

View of the crystal along two perpendicular directions


 

Table 1.  Crystal data and structure refinement for sugar.

X-ray lab book No.

1255

Crystal ID

M.M. sugar

Empirical formula

C12H22O11

Formula weight

342.3

Temperature

223(2) K

Wavelength

0.71073 Å

Crystal size

0.42 ´ 0.40 ´ 0.38 mm3

Crystal habit

colorless prism

Crystal system

Monoclinic

Space group

P21

Unit cell dimensions

a = 7.7441(5) Å

a = 90°

 

b = 8.6932(6) Å

b = 102.930(1)°

 

c = 10.8537(7) Å

g = 90°

Volume

712.16(8) Å3

Z

2

Density, ρcalc

1.596 g/cm3

Absorption coefficient, μ

0.143 mm-1

F(000)

364 ē

Diffractometer

Bruker Smart1000 CCD area detector

Radiation source

fine-focus sealed tube, MoKa

Generator power

20 kV, 5 mA

Detector distance

4.99 cm

Detector resolution

8.33 pixels/mm

Total frames

1150

Frame size

512 pixels

Frame width

0.5 °

Exposure per frame

8 sec

Total measurement time

4.8 hours

Data collection method

w scans

θ range for data collection

2.70 to 27.98°

Index ranges

-10 £  h £  10, -11 £  k £  11, -14 £  l £  13

Reflections collected

6859

Independent reflections

3324

Observed reflection, I>2σ(I)

3274

Coverage of independent reflections

99.30%

Variation in check reflections

-0.27%

Absorption correction

Semi-empirical from equivalents

 

SADABS (Sheldrick, 1996)

Max. and min. transmission

0.947 and 0.875

Structure solution technique

direct

Structure solution program

SHELXS-97 (Sheldrick, 1990)

Refinement technique

Full-matrix least-squares on F2

Refinement program

SHELXL-97 (Sheldrick, 1997)

Function minimized

Sw(Fo2 - Fc2)2

Data / restraints / parameters

3324 / 1 / 276

Goodness-of-fit on F2

1

Δ/σmax

0

Final R indices:

R1,   I>2σ(I)

0.0243

 

wR2, all data

0.0533

 

Rint

0.0152

 

Rsig

0.0176

Weighting scheme

w = 1/[σ2(Fo2) + (0.0093P)2 + 0.3P],

 

P = [max(Fo2 ,0) + 2Fo2]/3

Absolute structure parameter

0.2(5)

Extinction coefficient

0.055(2)

Largest diff. peak and hole

0.282 and -0.152 ē/Å3  

R1 = S||Fo|-|Fc||/S|Fo|,    wR2 = [Sw(Fo2-Fc2)2/Sw(Fo2)2]1/2

  

 

Table 2. Atomic coordinates and equivalent* isotropic atomic
               displacement parameters (Å2) for sugar.

Atom

x/a

y/b

z/c

Ueq

O1

0.36842(12)

0.22565(10)

0.37782(8)

0.01881(19)

C1

0.48593(16)

0.26651(14)

0.29995(11)

0.0161(2)

C2

0.63682(17)

0.14925(15)

0.31305(12)

0.0180(2)

O21

0.74897(13)

0.18838(12)

0.22894(9)

0.0227(2)

C3

0.56508(17)

-0.01297(15)

0.28551(12)

0.0194(3)

O31

0.70425(15)

-0.12470(13)

0.30889(10)

0.0292(2)

C4

0.44331(18)

-0.04735(15)

0.37476(12)

0.0204(3)

O41

0.35526(16)

-0.19069(12)

0.34880(12)

0.0339(3)

C5

0.29546(17)

0.07205(15)

0.35968(12)

0.0193(2)

C51

0.18465(18)

0.05284(17)

0.45849(13)

0.0240(3)

O52

0.28694(15)

0.07850(13)

0.58253(9)

0.0274(2)

O11

0.39148(11)

0.27659(10)

0.17102(8)

0.01626(18)

C6

0.36988(15)

0.43172(14)

0.12389(11)

0.0157(2)

C61

0.54506(16)

0.49276(15)

0.10252(13)

0.0199(3)

O62

0.62176(12)

0.38698(13)

0.02884(9)

0.0232(2)

C7

0.21435(16)

0.43410(15)

0.00673(11)

0.0166(2)

O71

0.20341(12)

0.30637(12)

-0.07509(9)

0.0211(2)

C8

0.05494(16)

0.45829(15)

0.06515(12)

0.0176(2)

O81

-0.09000(12)

0.52866(13)

-0.02157(9)

0.0238(2)

O6

0.31752(11)

0.52989(11)

0.21236(8)

0.01868(19)

C9

0.12882(16)

0.56372(15)

0.17671(12)

0.0182(2)

C91

0.04796(18)

0.54302(17)

0.29011(13)

0.0233(3)

O92

0.04017(13)

0.38555(13)

0.32689(10)

0.0262(2)

H11

0.534(2)

0.363(2)

0.3309(15)

0.019

H21

0.707(2)

0.1536(19)

0.3994(16)

0.022

H211

0.833(3)

0.245(2)

0.2680(17)

0.034

H31

0.499(2)

-0.019(2)

0.1989(16)

0.023

H311

0.738(3)

-0.139(2)

0.244(2)

0.044

H41

0.515(2)

-0.043(2)

0.4592(15)

0.025

H411

0.422(3)

-0.252(3)

0.348(2)

0.051

H51

0.222(2)

0.061(2)

0.2777(15)

0.023

H511

0.140(2)

-0.052(2)

0.4497(17)

0.029

H512

0.084(2)

0.120(2)

0.4386(17)

0.029

H521

0.283(3)

0.164(3)

0.600(2)

0.041

H611

0.524(2)

0.592(2)

0.0555(15)

0.024

H612

0.622(2)

0.511(2)

0.1846(15)

0.024

H621

0.655(2)

0.312(2)

0.0755(18)

0.035

H71

0.227(2)

0.526(2)

-0.0439(14)

0.02

H711

0.183(2)

0.232(2)

-0.0367(17)

0.032

H81

0.021(2)

0.363(2)

0.0946(15)

0.021

H811

-0.177(3)

0.486(3)

-0.0154(19)

0.043(6)

H91

0.114(2)

0.668(2)

0.1530(15)

0.022

H911

-0.073(2)

0.576(2)

0.2698(16)

0.028

H912

0.114(2)

0.606(2)

0.3633(16)

0.028

H921

0.143(3)

0.354(2)

0.3444(18)

0.039

* Ueq is defined as one third of the trace of the orthogonalized Uij tensor.

 

    

Table 3.  Anisotropic atomic displacement parameters *2) for sugar.

Atom

U11

U22

U33

U23

U13

U12

O1

0.0221(4)

0.0174(4)

0.0189(4)

-0.0001(3)

0.0086(4)

-0.0006(3)

C1

0.0174(5)

0.0164(6)

0.0149(5)

-0.0007(4)

0.0043(4)

-0.0004(4)

C2

0.0176(6)

0.0195(6)

0.0169(5)

0.0015(5)

0.0035(4)

0.0017(5)

O21

0.0183(4)

0.0257(5)

0.0255(5)

0.0011(4)

0.0080(4)

-0.0003(4)

C3

0.0239(6)

0.0177(6)

0.0176(6)

0.0006(5)

0.0065(5)

0.0028(5)

O31

0.0395(6)

0.0241(5)

0.0286(5)

0.0068(4)

0.0171(5)

0.0138(4)

C4

0.0256(6)

0.0154(6)

0.0217(6)

-0.0006(5)

0.0083(5)

-0.0017(5)

O41

0.0370(6)

0.0164(5)

0.0524(7)

-0.0045(5)

0.0190(5)

-0.0053(4)

C5

0.0204(6)

0.0191(6)

0.0183(6)

0.0010(5)

0.0045(5)

-0.0033(5)

C51

0.0223(6)

0.0254(7)

0.0264(6)

0.0048(5)

0.0099(5)

0.0003(5)

O52

0.0364(6)

0.0270(5)

0.0216(4)

0.0037(4)

0.0124(4)

0.0059(5)

O11

0.0179(4)

0.0136(4)

0.0167(4)

0.0007(3)

0.0025(3)

-0.0011(3)

C6

0.0148(5)

0.0148(6)

0.0178(5)

-0.0001(5)

0.0047(4)

0.0001(4)

C61

0.0150(5)

0.0203(6)

0.0255(6)

0.0010(5)

0.0067(5)

-0.0027(5)

O62

0.0197(4)

0.0281(5)

0.0246(5)

0.0037(4)

0.0104(4)

0.0021(4)

C7

0.0162(5)

0.0165(6)

0.0177(5)

0.0009(5)

0.0046(4)

-0.0009(4)

O71

0.0241(5)

0.0205(5)

0.0189(4)

-0.0030(4)

0.0051(4)

-0.0023(4)

C8

0.0149(5)

0.0183(6)

0.0197(6)

0.0027(5)

0.0043(4)

0.0005(5)

O81

0.0140(4)

0.0292(5)

0.0272(5)

0.0056(4)

0.0022(4)

0.0016(4)

O6

0.0147(4)

0.0196(4)

0.0213(4)

-0.0052(3)

0.0032(3)

0.0011(3)

C9

0.0151(6)

0.0169(6)

0.0228(6)

0.0001(5)

0.0049(5)

0.0020(4)

C91

0.0210(6)

0.0261(7)

0.0249(6)

-0.0030(5)

0.0097(5)

0.0013(5)

O92

0.0215(5)

0.0298(5)

0.0290(5)

0.0054(4)

0.0093(4)

0.0009(4)

* The anisotropic atomic displacement factor exponent takes the form: -2p2 [ h2a*2U11 + ... + 2hka*b*U12 ]

 

 

Table 4.  Bond lengths (Å), valence and torsion angles (°) for sugar.

O1-C1

1.4188(14)

 

O1-C5

1.4460(16)

 

C1-O11

1.4293(14)

C1-C2

1.5331(17)

 

C1-H11

0.951(17)

 

C2-O21

1.4347(16)

C2-C3

1.5206(18)

 

C2-H21

0.974(16)

 

O21-H211

0.85(2)

C3-O31

1.4307(16)

 

C3-C4

1.5251(17)

 

C3-H31

0.965(16)

O31-H311

0.81(2)

 

C4-O41

1.4181(17)

 

C4-C5

1.5269(18)

C4-H41

0.961(16)

 

O41-H411

0.75(2)

 

C5-C51

1.5252(17)

C5-H51

0.948(16)

 

C51-O52

1.4186(17)

 

C51-H511

0.977(19)

C51-H512

0.958(19)

 

O52-H521

0.77(2)

 

O11-C6

1.4388(15)

C6-O6

1.4104(14)

 

C6-C61

1.5221(16)

 

C6-C7

1.5436(16)

C61-O62

1.4319(16)

 

C61-H611

0.995(17)

 

C61-H612

0.968(16)

O62-H621

0.83(2)

 

C7-O71

1.4124(15)

 

C7-C8

1.5233(17)

C7-H71

0.987(17)

 

O71-H711

0.80(2)

 

C8-O81

1.4308(15)

C8-C9

1.5243(18)

 

C8-H81

0.950(17)

 

O81-H811

0.78(2)

O6-C9

1.4555(14)

 

C9-C91

1.5114(17)

 

C9-H91

0.943(18)

C91-O92

1.4310(18)

 

C91-H911

0.958(18)

 

C91-H912

1.007(18)

O92-H921

0.83(2)

 

 

 

 

 

 

 

 

 

 

 

 

 

 

C1-O1-C5

115.67(9)

 

O1-C1-O11

110.04(9)

 

O1-C1-C2

110.82(10)

O11-C1-C2

110.12(10)

 

O1-C1-H11

105.2(9)

 

O11-C1-H11

111.4(10)

C2-C1-H11

109.2(9)

 

O21-C2-C3

109.96(10)

 

O21-C2-C1

109.92(10)

C3-C2-C1

111.16(10)

 

O21-C2-H21

108.4(10)

 

C3-C2-H21

109.1(10)

C1-C2-H21

108.3(10)

 

C2-O21-H211

108.9(12)

 

O31-C3-C2

111.54(11)

O31-C3-C4

107.62(10)

 

C2-C3-C4

107.91(10)

 

O31-C3-H31

110.5(10)

C2-C3-H31

109.2(10)

 

C4-C3-H31

110.0(9)

 

C3-O31-H311

109.1(15)

O41-C4-C3

112.59(11)

 

O41-C4-C5

105.09(11)

 

C3-C4-C5

110.74(11)

O41-C4-H41

112.2(10)

 

C3-C4-H41

106.8(9)

 

C5-C4-H41

109.4(10)

C4-O41-H411

109.1(18)

 

O1-C5-C51

105.63(11)

 

O1-C5-C4

110.63(10)

C51-C5-C4

112.12(11)

 

O1-C5-H51

110.9(10)

 

C51-C5-H51

109.5(10)

C4-C5-H51

108.1(10)

 

O52-C51-C5

111.57(11)

 

O52-C51-H511

110.6(11)

C5-C51-H511

106.2(10)

 

O52-C51-H512

111.7(11)

 

C5-C51-H512

109.3(11)

H511-C51-H512

107.3(14)

 

C51-O52-H521

110.0(16)

 

C1-O11-C6

113.51(9)

O6-C6-O11

110.69(9)

 

O6-C6-C61

107.14(10)

 

O11-C6-C61

110.13(10)

O6-C6-C7

105.23(9)

 

O11-C6-C7

108.22(10)

 

C61-C6-C7

115.31(10)

O62-C61-C6

110.88(10)

 

O62-C61-H611

108.1(10)

 

C6-C61-H611

109.2(10)

O62-C61-H612

111.7(10)

 

C6-C61-H612

107.7(9)

 

H611-C61-H612

109.2(14)

C61-O62-H621

105.8(13)

 

O71-C7-C8

115.47(10)

 

O71-C7-C6

115.68(10)

C8-C7-C6

102.39(9)

 

O71-C7-H71

106.7(9)

 

C8-C7-H71

108.0(9)

C6-C7-H71

108.3(9)

 

C7-O71-H711

107.2(14)

 

O81-C8-C7

112.01(10)

O81-C8-C9

111.42(11)

 

C7-C8-C9

102.62(10)

 

O81-C8-H81

111.1(10)

C7-C8-H81

109.4(10)

 

C9-C8-H81

110.0(10)

 

C8-O81-H811

107.8(15)

C6-O6-C9

111.45(9)

 

O6-C9-C91

109.49(10)

 

O6-C9-C8

105.41(10)

C91-C9-C8

115.15(11)

 

O6-C9-H91

108.8(10)

 

C91-C9-H91

106.7(10)

C8-C9-H91

111.1(10)

 

O92-C91-C9

113.08(11)

 

O92-C91-H911

104.3(11)

C9-C91-H911

109.9(10)

 

O92-C91-H912

110.4(10)

 

C9-C91-H912

110.3(10)

H911-C91-H912

108.6(14)

 

C91-O92-H921

106.5(14)

 

 

 

 

 

 

 

 

 

 

 

C5-O1-C1-O11

67.51(12)

 

C5-O1-C1-C2

-54.53(13)

 

O1-C1-C2-O21

177.12(10)

O11-C1-C2-O21

55.13(13)

 

O1-C1-C2-C3

55.14(13)

 

O11-C1-C2-C3

-66.85(13)

O21-C2-C3-O31

63.45(13)

 

C1-C2-C3-O31

-174.59(10)

 

O21-C2-C3-C4

-178.54(10)

C1-C2-C3-C4

-56.59(13)

 

O31-C3-C4-O41

-65.28(14)

 

C2-C3-C4-O41

174.22(11)

O31-C3-C4-C5

177.39(11)

 

C2-C3-C4-C5

56.89(13)

 

C1-O1-C5-C51

176.52(10)

C1-O1-C5-C4

54.97(13)

 

O41-C4-C5-O1

-177.20(10)

 

C3-C4-C5-O1

-55.36(13)

O41-C4-C5-C51

65.17(14)

 

C3-C4-C5-C51

-173.00(11)

 

O1-C5-C51-O52

-56.70(14)

C4-C5-C51-O52

63.88(15)

 

O1-C1-O11-C6

108.32(11)

 

C2-C1-O11-C6

-129.23(10)

C1-O11-C6-O6

-44.83(12)

 

C1-O11-C6-C61

73.46(12)

 

C1-O11-C6-C7

-159.66(9)

O6-C6-C61-O62

171.14(10)

 

O11-C6-C61-O62

50.68(13)

 

C7-C6-C61-O62

-72.13(14)

O6-C6-C7-O71

-157.61(9)

 

O11-C6-C7-O71

-39.24(13)

 

C61-C6-C7-O71

84.58(13)

O6-C6-C7-C8

-31.15(12)

 

O11-C6-C7-C8

87.21(11)

 

C61-C6-C7-C8

-148.97(11)

O71-C7-C8-O81

-78.53(14)

 

C6-C7-C8-O81

154.88(10)

 

O71-C7-C8-C9

161.85(10)

C6-C7-C8-C9

35.26(12)

 

O11-C6-O6-C9

-102.24(11)

 

C61-C6-O6-C9

137.66(10)

C7-C6-O6-C9

14.45(12)

 

C6-O6-C9-C91

132.70(11)

 

C6-O6-C9-C8

8.28(13)

O81-C8-C9-O6

-147.55(10)

 

C7-C8-C9-O6

-27.53(12)

 

O81-C8-C9-C91

91.66(13)

C7-C8-C9-C91

-148.32(11)

 

O6-C9-C91-O92

-70.06(14)

 

C8-C9-C91-O92

48.48(16) 

 

 

Table 6.  Hydrogen bond information for sugar (Å and °).

D¾H¼A*

d(D¾H)

d(H¼A)

d(D¼A)

Ð(DHA)

O21¾H211¼O92I

0.85(2)

2.01(2)

2.8427(15)

168.8(17)

O31¾H311¼O71II

0.81(2)

2.04(2)

2.8499(14)

173(2)

O41¾H411¼O6III

0.75(2)

2.42(2)

2.8257(14)

115(2)

O52¾H521¼O31IV

0.77(2)

2.07(2)

2.8310(16)

166(2)

O62¾H621¼O21

0.83(2)

1.98(2)

2.7768(14)

160.9(19)

O71¾H711¼O81V

0.80(2)

2.07(2)

2.8483(15)

166.1(18)

O81¾H811¼O62VI

0.78(2)

1.93(2)

2.7102(14)

171(2)

O92¾H921¼O1

0.83(2)

2.03(2)

2.8409(14)

166(2)

* D - donor atom, H - hydrogen, A - acceptor.

Symmetry codes: (I) x+1,y,z; (II) -x+1,y-1/2,-z; (III) x,y-1,z; (IV) -x+1,y+1/2,-z+1; (V) -x,y-1/2,-z; (VI) x-1,y,z