A paracetamol–morpholine adduct

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Iain D. H. Oswaldet al. C8H9NO22.5C4H9NO DOI: 10.1107/S1600536802018111 Acta Cryst.(2002). E58, o1290±o1292 Acta Crystallographica Section E

Structure Reports

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ISSN 1600-5368

A paracetamol±morpholine adduct

Iain D. H. Oswald,a* W. D. Sam Motherwell,bSimon Parsonsa and Colin R. Pulhama

aSchool of Chemistry, The University of Edinburgh, King's Buildings, West Mains Road, Edinburgh EH9 3JJ, Scotland, andbCambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, England

Correspondence e-mail: iain.oswald@ed.ac.uk

Key indicators

Single-crystal X-ray study

T= 150 K

Mean(C±C) = 0.005 AÊ Disorder in solvent or counterion

Rfactor = 0.054

wRfactor = 0.178

Data-to-parameter ratio = 13.9

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

#2002 International Union of Crystallography Printed in Great Britain ± all rights reserved

Paracetamol [also known as acetaminophen orN -(4-hydroxy-phenyl)acetamide] is an important analgesic drug that has recently been cocrystallized with a series of cyclic N- and O-donor compounds. This paper describes the formation of a paracetamol adduct with morpholine, viz. paracetamol± morpholine (1/2.5), C8H9NO22.5C4H9NO. There are ®ve

morpholine molecules and two paracetamol molecules in the unit cell. The paracetamol molecules are held together by hydrogen bondingviamorpholine molecules, one of which is disordered about an inversion centre.

Comment

Paracetamol (acetaminophen) in its various polymorphic forms has been studied extensively in recent years. It has been shown (Fachaux et al., 1995) that the different polymorphs (monoclinic and orthorhombic) have different compressive properties. This ability for plastic deformation is of great interest to the pharmaceutical industry. The monoclinic form is the thermodynamically more stable form of paracetamol under normal conditions, but shows no plastic deformation. The orthorhombic polymorph is much harder to prepare and, so far, can only be obtained reproducibly from the melt or by seeding a saturated solution (Nichols & Frampton, 1998). This polymorph possesses plastic deformation and, therefore, mass production of this form would facilitate the manufacture of paracetamol for pharmaceutical purposes. In a recent study, our group has explored the use of cocrystals as a means of producing the orthorhombic polymorph. Paracetamol was found to cocrystallize with a number of different solvents (Oswald et al., 2002). Though the majority of the cocrystals formed were hemisolvates, we also produced a 1:2.5 cocrystal, (I), of paracetamol with morpholine.

There are two and a half morpholine molecules (designated

A,BandC; see Fig. 1) present in the asymmetric unit of (I). One of the morpholine molecules (C) is disordered over a crystallographic inversion centre, with the N and O atoms sharing an equivalent site. A composite scattering factor [0.5f(N) + 0.5f(O)] was used for this site. The hydrogen occupancy was ®xed at 0.5 in an axial position, which was inferred from a difference map.

The amine function of morpholine is a weak hydrogen-bond acceptor and a moderately strong donor. The ether moiety is a

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rather weak acceptor. In paracetamol, the amide and hydroxyl groups are strong donors, and the carbonyl group a strong acceptor; the hydroxyl group is a weak acceptor. The structure of adduct (I) is consistent with this hierarchy of interactions. All direct links between paracetamol molecules are absent in the structure of (I) (Fig. 2). Successive paracetamol molecules, related by lattice repeats along c, are linked via pairs of crystallographically independent morpholine molecules

through C O HÐN, O HÐN and N HÐN

interac-tions. This scheme establishes a chain of molecules in the series paracetamol±morpholine (B)±morpholine (A )±para-cetamol, which can be described with aC33(11) graph at the

ternary level (Bernsteinet al., 1995). A second chain is related to thisviaa crystallographic inversion centre, and is linked to the ®rstviaOÐH N hydrogen bonds to morpholine B, to form a ribbon-like structure. This scheme satis®es all the hydrogen-bonding characteristics of the paracetamol mol-ecules, with the exception of the weak OH acceptor func-tionality, although this arguably interacts with an aromatic CH group (O H = 2.62 AÊ). The hydrogen-bonding functionality of the morpholine is also satis®ed with the exception of the donor character of the ether moiety in molecule A. It is notable that, in order to accommodate this scheme, the morpholine moleculesAandBare in different conformations, with the amino H adopting the expected equatorial position in moleculeB, but the less favourable axial position in molecule

A.

Neighbouring ribbons are related to each other by inversion centres, which are occupied by a third crystallographically

independent molecule of morpholine (C). This molecule is disordered about the inversion centre, but forms weak hydrogen bonds [2.59 (5) AÊ] to one of the ether moieties of the two morpholine A molecules related by the inversion centre. Overall then, the structure of (I) consists of layers formed by weakly connected ribbons. The layers are formed parallel to the (120) planes. The distance between the mean paracetamol planes in successive layers alternates between 5.32 and 4.03 AÊ. The average distance, 4.68 AÊ, is commensu-rate with d(120) (4.55 AÊ). The mean planes of all the morpholine molecules are perpendicular to the plane of the paracetamol molecule. The angles that the mean planes of moleculesA, BandCmake with the paracetamol plane are 83.73 (10), 79.60 (10) and 75.15 (16), respectively. The

para-cetamol molecules thus form a `groove' in the layers, which align so that the morpholine molecules lie above and below this `groove' in successive layers.

The large number of solvent molecules within this structure has resulted in the formation of solvent bridges between the paracetamol molecules, with no paracetamol±paracetamol interactions, as seen in our previous study.

Experimental

Starting materials were obtained from Sigma±Aldrich and were used as received. Paracetamol (0.49 g, 3.24 mmol) was re¯uxed in 1 ml morpholine (11.42 mmol) and allowed to cool. Pale-yellow crystals were formed on maintaining the solution at 277 K.

Acta Cryst.(2002). E58, o1290±o1292 Iain D. H. Oswaldet al. C8H9NO22.5C4H9NO

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Figure 2

A section of the structure of the title paracetamol±morpholine (1/2.5) adduct. The view is along thebaxis. O atoms are shown in red, N atoms in blue, C atoms in green and H atoms in grey. Paracetamol molecules within the outlined unit cell are generated from those shown by translation along the (210) direction.

Figure 1

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Iain D. H. Oswaldet al. C8H9NO22.5C4H9NO Acta Cryst.(2002). E58, o1290±o1292

Crystal data

C8H9NO22.5C4H9NO Mr= 368.97 Triclinic,P1

a= 8.710 (4) AÊ

b= 9.920 (5) AÊ

c= 12.385 (5) AÊ

= 102.35 (3) = 108.33 (2) = 96.68 (3) V= 972.7 (7) AÊ3

Z= 2

Dx= 1.260 Mg mÿ3

CuKradiation Cell parameters from 48

re¯ections

= 20±22 = 0.74 mmÿ1 T= 150 (2) K Plate, colourless 0.270.230.06 mm

Data collection

Stoe Stadi-4 four-circle diffractometer

!±scans

Absorption correction: empirical

via scans [SHELXTL

(Sheldrick (2001) based on method of Northet al.(1968)]

Tmin= 0.717,Tmax= 0.889

3596 measured re¯ections 3416 independent re¯ections

1951 re¯ections withI> 2(I)

Rint= 0.028

max= 70.3 h=ÿ10!10

k=ÿ12!11

l=ÿ14!15 3 standard re¯ections

frequency: 120 min intensity decay: 5%

Re®nement

Re®nement onF2 R[F2> 2(F2)] = 0.054 wR(F2) = 0.178 S= 1.03 3416 re¯ections 246 parameters

H-atom parameters constrained

w= 1/[2(Fo2) + (0.0983P)2

+ 0.3346P]

whereP= (Fo2+ 2Fc2)/3

(/)max< 0.001 max= 0.35 e AÊÿ3 min=ÿ0.26 e AÊÿ3

Extinction correction:SHELXL97 Extinction coef®cient: 0.0077 (14)

The diffractometer was equipped with an Oxford Cryosystems low-temperature device operating at 150 K. H atoms were placed in

calculated positions and allowed to ride on their parent atoms, except for those involved in hydrogen bonding, which were located in a difference map; these were treated with a riding model, following several cycles of re®nement in which a CÐH distance restraint of 0.9 AÊ was applied.

Data collection:DIF4 (Stoe & Cie, 1990); cell re®nement:DIF4; data reduction:REDU4 (Stoe & Cie, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL(Sheldrick, 2001); software used to prepare material for publication:SHELXTLandCAMERON(Watkinet al., 1996).

The authors thank the EPSRC and Cambridge Crystal-lographic Data Centre for funding.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995).Angew. Chem. Int. Ed. Engl.34, 1555±1573.

Fachaux, J.-M., Guyot-Hermann, A.-M., Con¯ant, P., Drache, M., Veesler, S. & Boiselle, R. (1995).Powder Technol.82, 123±128.

Nichols, G. & Frampton, C. S. (1998).J. Pharm. Sci.87, 684±693.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968).Acta Cryst.A24, 351± 359.

Oswald, I. D. H., Allan, D. R., McGregor, P. A., Motherwell, W. D. S., Parsons, S. & Pulham, C. R. (2002).Acta Cryst.B58. In the press.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.

Sheldrick, G. M. (2001).SHELXTL.Version 6. Bruker AXS Inc., Madison, Wisconsin, USA.

Stoe & Cie (1990).DIF4 andREDU4. Stoe & Cie, Darmstadt, Germany. Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996).CAMERON. Chemical

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Acta Cryst. (2002). E58, o1290–o1292

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Acta Cryst. (2002). E58, o1290–o1292 [https://doi.org/10.1107/S1600536802018111]

A paracetamol

morpholine adduct

Iain D. H. Oswald, W. D. Sam Motherwell, Simon Parsons and Colin R. Pulham

N-(4-hydroxyphenyl)acetamide–morpholine (1/2.5)

Crystal data

C8H9NO2·2.5C4H9NO Mr = 368.97

Triclinic, P1 Hall symbol: -P 1 a = 8.710 (4) Å b = 9.920 (5) Å c = 12.385 (5) Å α = 102.35 (3)° β = 108.33 (2)° γ = 96.68 (3)° V = 972.7 (7) Å3

Z = 2 F(000) = 400 Dx = 1.260 Mg m−3

Cu radiation, λ = 1.54184 Å Cell parameters from 48 reflections θ = 20–22°

µ = 0.74 mm−1 T = 150 K Plate, colourless 0.27 × 0.23 × 0.06 mm

Data collection

Stoe Stadi-4 four-circle diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

ωθ scans

Absorption correction: empirical (using intensity measurements)

via ψ scans [SHELXTL (Sheldrick (2001) based on method of North et al. (1968)]

Tmin = 0.717, Tmax = 0.889

3596 measured reflections 3416 independent reflections 1951 reflections with I > 2σ(I) Rint = 0.028

θmax = 70.3°, θmin = 3.9° h = −10→10

k = −12→11 l = −14→15

3 standard reflections every 120 min

Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.054 wR(F2) = 0.178 S = 1.03 3416 reflections 246 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: calc/difmap H-atom parameters constrained w = 1/[σ2(F

o2) + (0.0983P)2 + 0.3346P] where P = (Fo2 + 2Fc2)/3

(Δ/σ)max < 0.001 Δρmax = 0.35 e Å−3 Δρmin = −0.26 e Å−3

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Acta Cryst. (2002). E58, o1290–o1292 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.

#=============================================================================== # PLATON/CHECK-(191101) versus check.def version of 16/11/01 for entry: parmor # Data From: parmor_e.cif - Data Type: CIF Bond Precision C—C = 0.0047 A # # CELL 1.54184 8.710 9.920 12.385 102.35 108.33 96.68 972.70 # SpaceGroup from Symmetry P-1 Hall: –P 1 # Reported P-1 ? # MoietyFormula 2(C8 H9 N O2), 5(C4 H9 N O) # Reported (C8H9NO2)(C4H9NO)2.5 # SumFormula C36 H63 N7 O9 # Reported C18 H31.50 N3.50 O4.50 # Mr = 737.93[Calc], 368.97[Rep] # Dx,gcm-3 = 1.260[Calc], 1.260[Rep] # Z = 1[Calc], 2[Rep] # Mu (mm-1) = 0.743[Calc], 0.743[Rep] # F000 = 400.0[Calc], 400.0[Rep] # Reported T limits: Tmin=0.717 Tmax=0.889 ′EMPIRICAL′ # Calculated T limits: Tmin=0.818 Tmin′=0.818 Tmax=0.956 # Reported Hmax= 10, Kmax= 12, Lmax= 15, Nref= 3416, Th(max)= 70.30 # Calculated Hmax= 10, Kmax= 12, Lmax= 15, Nref= 3712 (3712), Ratio= 0.92 (0.92) # R= 0.0538 (1951), wR2= 0.1782 (3416), S = 1.031, Npar= 246

#=============================================================================== >>> The Following ALERTS were generated <<<

028_ALERT A -diffrn-measured-fraction-theta-max low ···.. 0.92 022_ALERT C Ratio Unique / Expected Reflections too Low.. 0.92 029_ALERT C -diffrn-measured-fraction-theta-full low ···.. 0.92

The data were collected on a four-circle using Cu-kα radiation. Certain regions of reciprocal space above 2θ=90° were shaded by the chi- circle, and this has resulted in a low -diffrn-measured-fraction-theta-max.

041_ALERT C Calc. and Rep. SumFormula Strings Differ.. ? 042_ALERT C Calc. and Rep. MoietyFormula Strings Differ.. ? 045_ALERT C Calculated and Reported Z differ by ···. 0.50 Ratio

These reflect our choice of formula unit.

062_ALERT C Rescale T(min) & T(max) by ···. 1.08 No action taken.

125_ALERT C No _symmetry_space_group_name_Hall given ···.. ? Corrected.

302_ALERT C Anion/Solvent Disorder ···.. 8.00 Perc. We know. See text.

340_ALERT C Low Bond Precision on C—C bonds (x 1000) Ang.. 5 Disordered structure.

790_ALERT C Centre of Gravity not Within Unit Cell: Resd.# 1 C8 H9 N O2 Fixed.

790_ALERT C Centre of Gravity not Within Unit Cell: Resd.# 2 C4 H9 N O 790_ALERT C Centre of Gravity not Within Unit Cell: Resd.# 3 C4 H9 N O 790_ALERT C Centre of Gravity not Within Unit Cell: Resd.# 4 C4 H9 N O

No action; the asymmetric unit was chosen to be discrete H-bonded fragment.

ALERT Level Summary 1 ALERT Level A = In General: Serious Problem 13 ALERT Level C = Check & Explain

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)

O1 0.3543 (3) 0.9687 (3) 0.32398 (19) 0.0407 (6)

H11 0.268 (6) 0.901 (5) 0.249 (4) 0.081 (14)*

C1 0.4893 (4) 1.0247 (3) 0.3041 (2) 0.0325 (7)

C2 0.6318 (4) 1.0856 (3) 0.4007 (2) 0.0340 (7)

H2 0.6327 1.0862 0.4761 0.041*

C3 0.7720 (4) 1.1452 (3) 0.3858 (2) 0.0320 (7)

H3 0.8668 1.1852 0.4515 0.038*

C4 0.7745 (3) 1.1470 (3) 0.2738 (2) 0.0298 (7)

C5 0.6316 (4) 1.0851 (3) 0.1770 (2) 0.0337 (7)

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C6 0.4907 (4) 1.0231 (3) 0.1915 (3) 0.0360 (7)

H6 0.3967 0.9802 0.1258 0.043*

N1 0.9251 (3) 1.2109 (3) 0.2681 (2) 0.0339 (6)

H1 1.010 (4) 1.254 (4) 0.345 (3) 0.047 (10)*

C7 0.9630 (4) 1.2134 (3) 0.1705 (3) 0.0331 (7)

O2 0.8622 (3) 1.1677 (3) 0.06987 (17) 0.0441 (6)

C8 1.1411 (4) 1.2719 (4) 0.1936 (3) 0.0406 (8)

H8A 1.1982 1.1958 0.1826 0.061*

H8B 1.1912 1.3301 0.2731 0.061*

H8C 1.1475 1.3272 0.1397 0.061*

N1A 1.1842 (3) 1.3434 (3) 0.5029 (2) 0.0360 (6)

H1A1 1.130 (4) 1.349 (4) 0.554 (3) 0.067 (13)*

C2A 1.2627 (4) 1.4925 (4) 0.5329 (3) 0.0432 (8)

H2A1 1.1792 1.5496 0.5312 0.052*

H2A2 1.3087 1.5067 0.4734 0.052*

C3A 1.3979 (4) 1.5420 (4) 0.6527 (3) 0.0468 (9)

H3A2 1.4504 1.6386 0.6652 0.056*

H3A1 1.3505 1.5393 0.7135 0.056*

O4A 1.5182 (3) 1.4553 (3) 0.6615 (2) 0.0513 (7)

C5A 1.4447 (4) 1.3107 (4) 0.6411 (3) 0.0492 (9)

H5A1 1.3981 1.3019 0.7014 0.059*

H5A2 1.5288 1.2538 0.6463 0.059*

C6A 1.3114 (4) 1.2577 (4) 0.5214 (3) 0.0460 (8)

H6A2 1.3612 1.2564 0.4614 0.055*

H6A1 1.2598 1.1618 0.5118 0.055*

N1B 0.8948 (3) 1.2115 (3) −0.1501 (2) 0.0369 (6)

H1B1 0.892 (5) 1.210 (4) −0.0788 (17) 0.059 (11)*

C2B 1.0423 (4) 1.1576 (4) −0.1578 (3) 0.0417 (8)

H2B1 1.0345 1.0628 −0.1485 0.050*

H2B2 1.1401 1.2167 −0.0956 0.050*

C3B 1.0541 (4) 1.1578 (4) −0.2767 (3) 0.0419 (8)

H3B2 1.1515 1.1230 −0.2827 0.050*

H3B1 0.9584 1.0951 −0.3383 0.050*

O4B 1.0631 (3) 1.2961 (2) −0.29388 (19) 0.0390 (6)

C5B 0.9246 (4) 1.3526 (4) −0.2823 (3) 0.0402 (8)

H5B1 0.8251 1.2963 −0.3446 0.048*

H5B2 0.9361 1.4476 −0.2912 0.048*

C6B 0.9085 (4) 1.3549 (4) −0.1638 (3) 0.0408 (8)

H6B2 1.0043 1.4159 −0.1011 0.049*

H6B1 0.8113 1.3911 −0.1592 0.049*

N1C 1.3689 (3) 1.4607 (3) 0.0409 (2) 0.0497 (7) 0.50

H1C1 1.430 (9) 1.511 (8) 0.115 (3) 0.074* 0.50

O1C 1.3689 (3) 1.4607 (3) 0.0409 (2) 0.0497 (7) 0.50

C2C 1.4703 (5) 1.3634 (5) 0.0125 (4) 0.0533 (10)

H2C2 1.429 (6) 1.311 (5) −0.082 (4) 0.083 (14)*

H2C1 1.479 (5) 1.299 (4) 0.062 (4) 0.065 (12)*

C3C 1.6388 (5) 1.4367 (5) 0.0272 (4) 0.0526 (10)

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Acta Cryst. (2002). E58, o1290–o1292

H3CB 1.705 (5) 1.357 (4) −0.004 (3) 0.057 (11)*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23

O1 0.0335 (12) 0.0548 (15) 0.0299 (11) −0.0078 (10) 0.0122 (9) 0.0101 (10)

C1 0.0303 (15) 0.0399 (18) 0.0292 (15) 0.0033 (13) 0.0136 (12) 0.0102 (13)

C2 0.0354 (16) 0.0444 (18) 0.0207 (13) 0.0003 (14) 0.0104 (12) 0.0089 (12)

C3 0.0335 (15) 0.0375 (17) 0.0222 (14) 0.0024 (13) 0.0080 (12) 0.0076 (12)

C4 0.0270 (14) 0.0369 (17) 0.0269 (14) 0.0038 (12) 0.0112 (12) 0.0098 (12)

C5 0.0316 (15) 0.0457 (19) 0.0227 (14) 0.0017 (13) 0.0091 (12) 0.0110 (13)

C6 0.0330 (16) 0.0464 (19) 0.0242 (14) −0.0020 (14) 0.0065 (12) 0.0106 (13)

N1 0.0304 (13) 0.0469 (16) 0.0248 (12) 0.0023 (12) 0.0106 (11) 0.0117 (11)

C7 0.0365 (16) 0.0383 (18) 0.0281 (15) 0.0033 (13) 0.0162 (13) 0.0111 (12)

O2 0.0371 (12) 0.0670 (16) 0.0249 (11) −0.0043 (11) 0.0098 (9) 0.0151 (10)

C8 0.0318 (16) 0.054 (2) 0.0377 (17) 0.0009 (15) 0.0153 (14) 0.0145 (15)

N1A 0.0312 (13) 0.0473 (16) 0.0297 (13) 0.0008 (12) 0.0130 (11) 0.0110 (11)

C2A 0.0427 (18) 0.048 (2) 0.0371 (17) 0.0049 (16) 0.0104 (15) 0.0147 (15)

C3A 0.0444 (19) 0.049 (2) 0.0386 (18) 0.0010 (17) 0.0082 (15) 0.0090 (15)

O4A 0.0330 (12) 0.0593 (16) 0.0555 (15) −0.0014 (11) 0.0059 (11) 0.0227 (12)

C5A 0.0384 (18) 0.057 (2) 0.051 (2) 0.0063 (16) 0.0102 (15) 0.0232 (17)

C6A 0.047 (2) 0.047 (2) 0.0412 (19) 0.0105 (16) 0.0120 (15) 0.0113 (15)

N1B 0.0341 (13) 0.0519 (17) 0.0249 (12) −0.0009 (12) 0.0115 (11) 0.0140 (11)

C2B 0.0391 (17) 0.050 (2) 0.0390 (17) 0.0056 (15) 0.0134 (14) 0.0193 (15)

C3B 0.0458 (19) 0.0421 (19) 0.0473 (19) 0.0106 (15) 0.0255 (16) 0.0165 (15)

O4B 0.0393 (12) 0.0470 (13) 0.0405 (12) 0.0065 (10) 0.0236 (10) 0.0182 (10)

C5B 0.0435 (18) 0.051 (2) 0.0327 (16) 0.0116 (16) 0.0187 (14) 0.0165 (14)

C6B 0.0446 (18) 0.050 (2) 0.0323 (16) 0.0067 (15) 0.0197 (14) 0.0111 (14)

N1C 0.0434 (15) 0.072 (2) 0.0432 (15) 0.0116 (14) 0.0223 (12) 0.0235 (14)

O1C 0.0434 (15) 0.072 (2) 0.0432 (15) 0.0116 (14) 0.0223 (12) 0.0235 (14)

C2C 0.053 (2) 0.062 (3) 0.052 (2) 0.0099 (19) 0.0241 (18) 0.023 (2)

C3C 0.047 (2) 0.070 (3) 0.052 (2) 0.0154 (19) 0.0216 (18) 0.0289 (19)

Geometric parameters (Å, º)

O1—C1 1.357 (3) C5A—C6A 1.505 (5)

O1—H11 1.02 (5) C5A—H5A1 0.9700

C1—C2 1.386 (4) C5A—H5A2 0.9700

C1—C6 1.394 (4) C6A—H6A2 0.9700

C2—C3 1.377 (4) C6A—H6A1 0.9700

C2—H2 0.9300 N1B—C6B 1.464 (4)

C3—C4 1.398 (4) N1B—C2B 1.470 (4)

C3—H3 0.9300 N1B—H1B1 0.895 (10)

C4—C5 1.390 (4) C2B—C3B 1.509 (4)

C4—N1 1.418 (4) C2B—H2B1 0.9700

C5—C6 1.388 (4) C2B—H2B2 0.9700

C5—H5 0.9300 C3B—O4B 1.429 (4)

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N1—C7 1.354 (4) C3B—H3B1 0.9700

N1—H1 0.97 (4) O4B—C5B 1.421 (4)

C7—O2 1.228 (4) C5B—C6B 1.513 (4)

C7—C8 1.505 (4) C5B—H5B1 0.9700

C8—H8A 0.9600 C5B—H5B2 0.9700

C8—H8B 0.9600 C6B—H6B2 0.9700

C8—H8C 0.9600 C6B—H6B1 0.9700

N1A—C6A 1.465 (4) N1C—C2C 1.444 (5)

N1A—C2A 1.471 (4) N1C—C3Ci 1.450 (4)

N1A—H1A1 0.892 (10) N1C—H1C1 0.903 (10)

C2A—C3A 1.512 (5) C2C—C3C 1.497 (5)

C2A—H2A1 0.9700 C2C—H2C2 1.09 (5)

C2A—H2A2 0.9700 C2C—H2C1 0.97 (4)

C3A—O4A 1.424 (4) C3C—O1Ci 1.450 (4)

C3A—H3A2 0.9700 C3C—N1Ci 1.450 (4)

C3A—H3A1 0.9700 C3C—H3CA 1.12 (4)

O4A—C5A 1.436 (4) C3C—H3CB 1.11 (4)

C1—O1—H11 112 (3) N1A—C6A—C5A 113.3 (3)

O1—C1—C2 117.9 (2) N1A—C6A—H6A2 108.9

O1—C1—C6 123.0 (3) C5A—C6A—H6A2 108.9

C2—C1—C6 119.1 (3) N1A—C6A—H6A1 108.9

C3—C2—C1 120.4 (3) C5A—C6A—H6A1 108.9

C3—C2—H2 119.8 H6A2—C6A—H6A1 107.7

C1—C2—H2 119.8 C6B—N1B—C2B 109.4 (3)

C2—C3—C4 121.3 (3) C6B—N1B—H1B1 111 (3)

C2—C3—H3 119.3 C2B—N1B—H1B1 106 (3)

C4—C3—H3 119.3 N1B—C2B—C3B 108.6 (3)

C5—C4—C3 118.1 (3) N1B—C2B—H2B1 110.0

C5—C4—N1 125.1 (3) C3B—C2B—H2B1 110.0

C3—C4—N1 116.8 (3) N1B—C2B—H2B2 110.0

C6—C5—C4 120.8 (3) C3B—C2B—H2B2 110.0

C6—C5—H5 119.6 H2B1—C2B—H2B2 108.3

C4—C5—H5 119.6 O4B—C3B—C2B 111.3 (3)

C5—C6—C1 120.4 (3) O4B—C3B—H3B2 109.4

C5—C6—H6 119.8 C2B—C3B—H3B2 109.4

C1—C6—H6 119.8 O4B—C3B—H3B1 109.4

C7—N1—C4 127.8 (3) C2B—C3B—H3B1 109.4

C7—N1—H1 118 (2) H3B2—C3B—H3B1 108.0

C4—N1—H1 114 (2) C5B—O4B—C3B 111.1 (2)

O2—C7—N1 123.2 (3) O4B—C5B—C6B 111.6 (3)

O2—C7—C8 121.7 (3) O4B—C5B—H5B1 109.3

N1—C7—C8 115.1 (3) C6B—C5B—H5B1 109.3

C7—C8—H8A 109.5 O4B—C5B—H5B2 109.3

C7—C8—H8B 109.5 C6B—C5B—H5B2 109.3

H8A—C8—H8B 109.5 H5B1—C5B—H5B2 108.0

C7—C8—H8C 109.5 N1B—C6B—C5B 108.9 (3)

(9)

supporting information

sup-6

Acta Cryst. (2002). E58, o1290–o1292

H8B—C8—H8C 109.5 C5B—C6B—H6B2 109.9

C6A—N1A—C2A 109.5 (3) N1B—C6B—H6B1 109.9

C6A—N1A—H1A1 115 (3) C5B—C6B—H6B1 109.9

C2A—N1A—H1A1 99 (3) H6B2—C6B—H6B1 108.3

N1A—C2A—C3A 113.2 (3) C2C—N1C—C3Ci 110.3 (3)

N1A—C2A—H2A1 108.9 C2C—N1C—H1C1 104 (6)

C3A—C2A—H2A1 108.9 C3Ci—N1C—H1C1 104 (6)

N1A—C2A—H2A2 108.9 N1C—C2C—C3C 112.5 (4)

C3A—C2A—H2A2 108.9 N1C—C2C—H2C2 113 (2)

H2A1—C2A—H2A2 107.8 C3C—C2C—H2C2 98 (2)

O4A—C3A—C2A 110.8 (3) N1C—C2C—H2C1 109 (2)

O4A—C3A—H3A2 109.5 C3C—C2C—H2C1 110 (2)

C2A—C3A—H3A2 109.5 H2C2—C2C—H2C1 114 (3)

O4A—C3A—H3A1 109.5 O1Ci—C3C—N1Ci 0.0 (2)

C2A—C3A—H3A1 109.5 O1Ci—C3C—C2C 111.8 (3)

H3A2—C3A—H3A1 108.1 N1Ci—C3C—C2C 111.8 (3)

C3A—O4A—C5A 111.2 (3) O1Ci—C3C—H3CA 113 (2)

O4A—C5A—C6A 110.7 (3) N1Ci—C3C—H3CA 113 (2)

O4A—C5A—H5A1 109.5 C2C—C3C—H3CA 105 (2)

C6A—C5A—H5A1 109.5 O1Ci—C3C—H3CB 108.3 (19)

O4A—C5A—H5A2 109.5 N1Ci—C3C—H3CB 108.3 (19)

C6A—C5A—H5A2 109.5 C2C—C3C—H3CB 108 (2)

H5A1—C5A—H5A2 108.1 H3CA—C3C—H3CB 111 (3)

Figure

Updating...

References

Related subjects : WEAK HYDROGEN BONDS r(GpG)-adduct