Powder study of 3-aza­bicyclo­[3.3.1]nonane-2,4-dione 1-methyl­naphthalene hemisolvate

Hulme, A.T.; Fernandes, P.; Florence, A.; Johnston, A.; Shankland, K.

doi:10.1107/S1600536806030078

organic compounds

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ISSN: 2056-9890

Volume 62| Part 9| September 2006| Pages o3752-o3754

https://doi.org/10.1107/S1600536806030078

Powder study of 3-azabicyclo[3.3.1]nonane-2,4-dione 1-methylnaphthalene hemisolvate

Ashley T Hulme,^a Philippe Fernandes,^b Alastair Florence,^b ^* Andrea Johnston ^b and Kenneth Shankland ^c

^aChristopher Ingold Laboratory, Department of Chemistry, University College London, 20 Gordon Street, London WC1H 0AJ, England, ^bSolid-State Research Group, Department of Pharmaceutical Sciences, University of Strathclyde, 27 Taylor Street, Glasgow G4 0NR, Scotland, and ^cISIS Facility, Rutherford Appleton Laboratory, Chilton, Didcot, Oxon, OX11 0QX, England
^*Correspondence e-mail: alastair.florence@strath.ac.uk

(Received 19 June 2006; accepted 1 August 2006; online 9 August 2006)

The crystal structure of the title compound, C₈H₁₁N₁O₂·0.5C₁₁H₁₀, was solved by simulated annealing from laboratory X-ray powder diffraction data, collected at room temperature. Subsequent Rietveld refinement, using data collected to 1.51 Å resolution, yielded an R_wp value of 0.057. The compound crystallizes with two molecules of 3-azabicyclononane-2,4-dione and one molecule of 1-methylnaphthalene in the asymmetric unit.

Comment

The title compound, (I), was crystallized from 1-methylnaphthalene during a preliminary solvent screen in preparation for an automated parallel crystallization study of 3-azabicyclo[3.3.1]nonane-2,4-dione. The sample was identified as a new form using multi-sample foil transmission X-ray powder diffraction analysis (Florence et al., 2003 ).

The crystal structure of (I) was solved by simulated annealing using laboratory X-ray powder diffraction data. The compound crystallizes in space group P2₁/c with two molecules of 3-azabicyclononane-2,4-dione and one molecule of 1-methylnaphthalene in the asymmetric unit (Fig. 1). In the crystal structure, intermolecular N—H⋯O hydrogen bonds (Table 1) link two independent 3-azabicyclononane-2,4-dione molecules into a chain (Fig. 1) running along the b axis. The structure of this chain is very similar to that found in the un-solvated form 1 of 3-azabicyclononane-2,4-dione (Howie & Skakle, 2001 ). However, in form 1 the chain is propagated by a glide symmetry operation, whereas in (I) it propagates via a 2₁ screw axis. The paired hydrogen-bonded chains in (I) constitute a pseudo-layer parallel to the bc plane. Between two pseudo-layers related by translation along the a axis, channels parallel to the b axis are observed. These channels are filled by stacks of 1-methylnaphthalene solvent molecules, which are oriented nearly perpendicular to the b axis (Fig. 2).

Figure 1
The asymmetric unit of (I)

, with the atom-numbering scheme. The dashed line indicates the N—H⋯O hydrogen bond between 3-azabicyclononane-2,4-dione molecules. Displacement spheres are shown at the 50% probability level.

Figure 2
The crystal packing of (I)

viewed down the b axis and showing the stacks of solvent molecules situated between the pseudo-layers formed by 3-azabicyclononane-2,4-dione molecules. Illustrated using PLATON (Spek, 2003

Figure 3
Final observed (points), calculated (line) and difference [(y_obs-y_calc)/σ(y_obs)] profiles for the Rietveld refinement of the title compound.

Experimental

A polycrystalline sample of (I) was recrystallized by cooling a saturated 1-methylnaphthalene solution from 313 to 283 K. The sample was loaded into a 0.7 mm borosilicate glass capillary and rotated throughout the data collection to minimize preferred orientation effects. Data were collected using a variable count time (VCT) scheme in which the step time is increased with 2θ (Shankland et al., 1997 ; Hill & Madsen, 2002 $[Hill, R. J. & Madsen, I. C. (2002). Structure Determination from Powder Diffraction Data, edited by W. I. F. David, K. Shankland, L. B. McCusker and Ch. Baerlocher, pp.114-116. Oxford University Press.]$ ).

Crystal data

C₈H₁₁NO₂·0.5C₁₁H₁₀
M_r = 224.28
Monoclinic, P 2₁ /c
a = 15.02360 (18) Å
b = 7.32295 (12) Å
c = 22.5164 (3) Å
β = 106.0201 (6)°
V = 2380.99 (6) Å³
Z = 8
D_x = 1.251 Mg m⁻³
Cu Kα₁ radiation
μ = 0.67 mm⁻¹
T = 295 K
Specimen shape: cylinder
12 × 0.7 × 0.7 mm
Specimen prepared at 298 K
Particle morphology: needle, white

Data collection

Bruker AXS D8 Advance diffractometer
Specimen mounting: 0.7 mm borosilicate capillary
Specimen mounted in transmission mode
Scan method: step
Absorption correction: none
2θ_min = 4.0, 2θ_max = 62.5°
Increment in 2θ = 0.017°

Refinement

R_p = 0.046
R_wp = 0.057
R_exp = 0.013
R_B = 3.499
S = 2.00
Profile function: Fundamental parameters with axial divergence correction.
211 parameters
Only H-atom coordinates refined
w = 1/σ(Y_obs)²
(Δ/σ)_max = 0.01
Preferred orientation correction: A spherical harmonics-based preferred orientation correction (Järvinen, 1993 ) was applied with TOPAS (Coelho, 2003 ) during the Rietveld refinement

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯O3	0.900 (5)	1.966 (6)	2.865 (2)	175.8 (4)
N2—H22⋯O2ⁱ	0.901 (5)	1.921 (10)	2.812 (8)	170.1 (5)
Symmetry code: (i) x, y+1, z.

The diffraction pattern indexed to a monoclinic cell [M(20) = 44.5, F(20) = 146.5; DICVOL91; Boultif & Louer, 1991 ] and the space group P2₁/c was assigned from volume considerations and a statistical consideration of the systematic absences (Markvardsen et al., 2001 ). The data set was background subtracted and truncated to 51.8° 2θ for Pawley fitting (Pawley, 1981 ; χ²_Pawley = 15.77) and the structure solved using the simulated annealing (SA) global optimization procedure, described previously (David et al., 1998 ), that is now implemented in the DASH computer program (David et al., 2001 ). The SA structure solution used 453 reflections and involved the optimization of three fragments totaling 18 degrees of freedom (six positional and orientational for each fragment present in the asymmetric unit). All degrees of freedom were assigned random values at the start of the simulated annealing. The best SA solution had a favourable χ²_SA/χ²_Pawley ratio of 3.47 and a chemically reasonable lattice packing arrangement, with no significant misfit to the diffraction data.

The solved structure was then refined against the data in the range 4–61.4° 2θ using a restrained Rietveld (1969 ) method as implemented in TOPAS (Coelho, 2003), with R_wp falling to 0.0566 during the refinement. All atomic positions (including H atoms) for the structure of (I) were refined, subject to a series of restraints on bond lengths, bond angles and planarity.

The restraints were set such that bonds and angles did not deviate more than 0.01 Å and 0.8°, respectively, from their initial values during the refinement. Atoms C12, C13, C15, C16, O1, N1, O2 and H1 (first molecule) and atoms C20, C21, C23, C24, O3, N2, O4 and H22 (second molecule) of 3-azabicyclo[3.3.1]nonane-2,4-dione were restrained to be coplanar. Restraints were also applied to the methylnaphthalene molecule, for planarity purposes. A spherical harmonics (4th order) correction of intensities for preferred orientation was applied in the final refinement (Järvinen, 1993). The observed and calculated diffraction patterns for the refined crystal structure are shown in Fig. 3. U_iso(H) values were fixed at 0.076 Å².

Data collection: DIFFRAC plus XRD Commander (Kienle & Jacob, 2003 ); cell refinement: TOPAS (Coelho, 2003); data reduction: DASH (David et al., 2001); program(s) used to solve structure: DASH; program(s) used to refine structure: TOPAS; molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON, enCIFer (Allen et al., 2004 ) and SHELXL97 (Sheldrick, 1997 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806030078/cv2076sup1.cif

Rietveld powder data: contains datablock I. DOI: https://doi.org/10.1107/S1600536806030078/cv2076Isup2.rtv

Computing details top

Data collection: DIFFRAC plus XRD Commander (Kienle & Jacob, 2003); data reduction: DASH (David et al., 2001); program(s) used to solve structure: DASH; program(s) used to refine structure: Topas (Coelho, 2003); software used to prepare material for publication: CAMERON (Watkin et al., 1996), enCIFer (Allen et al., 2004) and SHELXL97 (Sheldrick, 1997).

3-azabicyclo[3.3.1]nonane-2,4-dione 1-methylnaphthalene hemisolvate top

Crystal data top

C₈H₁₁NO₂·0.5C₁₁H₁₀	Z = 8
M_r = 224.28	F(000) = 960
Monoclinic, P2₁/c	D_x = 1.251 Mg m⁻³
Hall symbol: -P 2ybc	Cu Kα₁ radiation, λ = 1.54056 Å
a = 15.02360 (18) Å	µ = 0.67 mm⁻¹
b = 7.32295 (12) Å	T = 295 K
c = 22.5164 (3) Å	white
β = 106.0201 (6)°	cylinder, 12 × 0.7 mm
V = 2380.99 (6) Å³	Specimen preparation: Prepared at 298 K

Data collection top

Bruker AXS D8 Advance diffractometer	Data collection mode: transmission
Radiation source: sealed X-ray tube, Bruker-AXS D8	Scan method: step
Primary focussing, Ge 111 monochromator	2θ_min = 4.0°, 2θ_max = 62.5°, 2θ_step = 0.017°
Specimen mounting: 0.7 mm borosilicate capillary

Refinement top

Least-squares matrix: selected elements only	201 restraints
R_p = 0.046	1 constraint
R_wp = 0.057	Only H-atom coordinates refined
R_exp = 0.013	Weighting scheme based on measured s.u.'s 1/σ(Y_obs)²
R_Bragg = 3.499	(Δ/σ)_max = 0.01
3387 data points	Background function: Chebyshev polynomial
Profile function: Fundamental parameters with axial divergence correction.	Preferred orientation correction: A spherical harmonics-based preferred orientation correction (Järvinen, 1993) was applied with Topas during the Rietveld refinement.
211 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	U_iso*/U_eq
C1	0.54315 (6)	0.4443 (3)	0.76875 (4)	0.0321 (8)*
C2	0.51206 (6)	0.4415 (5)	0.70448 (4)	0.0321 (8)*
C3	0.57567 (6)	0.4424 (5)	0.66958 (4)	0.0321 (8)*
C4	0.67010 (6)	0.4485 (4)	0.69889 (4)	0.0321 (8)*
C5	0.70105 (6)	0.4487 (4)	0.76294 (4)	0.0321 (8)*
C6	0.63774 (5)	0.4471 (4)	0.79780 (4)	0.0321 (8)*
C7	0.54443 (6)	0.4412 (4)	0.60537 (4)	0.0321 (8)*
C8	0.45010 (6)	0.4434 (4)	0.57598 (4)	0.0321 (8)*
C9	0.38669 (6)	0.4450 (4)	0.61066 (4)	0.0321 (8)*
C10	0.41743 (6)	0.4445 (4)	0.67475 (4)	0.0321 (8)*
H1	0.6592 (2)	0.4473 (9)	0.84165 (15)	0.0760*
H2	0.7135 (2)	0.4490 (9)	0.67509 (16)	0.0760*
H3	0.7657 (2)	0.4497 (9)	0.78299 (16)	0.0760*
H4	0.5877 (2)	0.4411 (9)	0.58152 (16)	0.0760*
H5	0.4290 (2)	0.4438 (9)	0.53217 (15)	0.0760*
H6	0.3222 (2)	0.4450 (9)	0.59045 (17)	0.0760*
H7	0.3738 (2)	0.4450 (9)	0.69837 (18)	0.0760*
C11	0.47485 (6)	0.44543 (14)	0.80686 (4)	0.0321 (8)*
H8	0.5076 (2)	0.4393 (8)	0.84951 (16)	0.0760*
H9	0.4346 (2)	0.3432 (7)	0.79622 (16)	0.0760*
H10	0.4393 (3)	0.5547 (7)	0.79910 (17)	0.0760*
N1	0.17867 (8)	0.20902 (12)	0.47851 (5)	0.0321 (8)*
H11	0.1574 (2)	0.3045 (8)	0.49575 (17)	0.0760*
C12	0.22707 (9)	0.2494 (13)	0.43608 (5)	0.0321 (8)*
O1	0.23991 (19)	0.4086 (2)	0.42479 (10)	0.0321 (8)*
C13	0.26293 (6)	0.09128 (13)	0.40697 (5)	0.0321 (8)*
H12	0.2652 (2)	0.1316 (8)	0.36728 (16)	0.0760*
C14	0.20052 (6)	−0.07379 (13)	0.40282 (5)	0.0321 (8)*
H13	0.2243 (2)	−0.1756 (8)	0.38588 (17)	0.0760*
H14	0.1404 (2)	−0.051 (8)	0.3763 (16)	0.0760*
C15	0.19727 (6)	−0.12209 (13)	0.46805 (4)	0.0321 (8)*
H15	0.156 (2)	−0.2206 (8)	0.46813 (17)	0.0760*
C16	0.15968 (9)	0.03559 (14)	0.49644 (5)	0.0321 (8)*
O2	0.1167 (12)	0.0194 (3)	0.53435 (8)	0.0321 (8)*
C17	0.29412 (6)	−0.17195 (12)	0.50824 (4)	0.0321 (8)*
H16	0.3104 (2)	−0.2788 (8)	0.48964 (17)	0.0760*
H17	0.288 (2)	−0.2007 (8)	0.54817 (18)	0.0760*
C18	0.36461 (6)	−0.02279 (13)	0.50985 (4)	0.0321 (8)*
H18	0.3513 (2)	0.0791 (8)	0.53214 (15)	0.0760*
H19	0.4252 (2)	−0.0652 (8)	0.53002 (16)	0.0760*
C19	0.36203 (6)	0.04481 (13)	0.44539 (4)	0.0321 (8)*
H20	0.3999 (2)	0.1491 (8)	0.44618 (17)	0.0760*
H21	0.3852 (2)	−0.0438 (9)	0.42271 (16)	0.0760*
N2	0.06436 (9)	0.71279 (13)	0.59201 (4)	0.0321 (8)*
H22	0.0757 (3)	0.8074 (8)	0.56961 (17)	0.0760*
C20	0.08087 (10)	0.53992 (14)	0.57266 (5)	0.0321 (8)*
O3	0.11144 (19)	0.5238 (3)	0.52816 (7)	0.0321 (8)*
C21	0.05876 (7)	0.38030 (13)	0.60806 (4)	0.0321 (8)*
H23	0.0424 (3)	0.2824 (8)	0.57937 (15)	0.0760*
C22	−0.01946 (6)	0.42824 (13)	0.63579 (4)	0.0321 (8)*
H24	−0.0324 (2)	0.3294 (7)	0.65950 (16)	0.0760*
H25	−0.0752 (2)	0.4521 (8)	0.60452 (15)	0.0760*
C23	0.01063 (7)	0.59259 (13)	0.67805 (4)	0.0321 (8)*
H26	−0.0373 (3)	0.6329 (8)	0.69504 (16)	0.0760*
C24	0.03020 (10)	0.75294 (13)	0.64179 (5)	0.0321 (8)*
O4	0.0208 (2)	0.9113 (2)	0.65479 (10)	0.0321 (8)*
C25	0.09695 (6)	0.54694 (13)	0.73074 (4)	0.0321 (8)*
H27	0.0770 (2)	0.4561 (7)	0.75432 (17)	0.0760*
H28	0.1135 (2)	0.6545 (7)	0.75490 (17)	0.0760*
C26	0.17607 (6)	0.47383 (13)	0.70790 (4)	0.0321 (8)*
H29	0.2010 (2)	0.5698 (8)	0.68908 (16)	0.0760*
H30	0.2239 (2)	0.4276 (8)	0.74153 (16)	0.0760*
C27	0.14519 (7)	0.32465 (12)	0.65954 (4)	0.0321 (8)*
H31	0.1923 (2)	0.2904 (8)	0.64094 (17)	0.0760*
H32	0.1301 (2)	0.2148 (8)	0.67711 (17)	0.0760*

Geometric parameters (Å, º) top

O1—C12	1.220 (9)	C25—C26	1.5171 (13)
O2—C16	1.210 (13)	C26—C27	1.5217 (13)
O3—C20	1.218 (2)	C21—H23	0.951 (5)
O4—C24	1.2138 (19)	C22—H24	0.951 (5)
N1—C16	1.3860 (14)	C22—H25	0.950 (3)
N1—C12	1.383 (3)	C23—H26	0.951 (5)
N1—H11	0.900 (5)	C25—H27	0.950 (4)
N2—C24	1.3870 (17)	C25—H28	0.951 (5)
N2—C20	1.3833 (15)	C26—H29	0.949 (5)
N2—H22	0.901 (5)	C26—H30	0.951 (4)
C12—C13	1.502 (7)	C27—H31	0.950 (4)
C13—C14	1.5168 (13)	C27—H32	0.951 (5)
C13—C19	1.5395 (14)	C1—C2	1.3927 (12)
C14—C15	1.5246 (14)	C1—C6	1.3909 (12)
C15—C17	1.5306 (13)	C1—C11	1.5084 (13)
C15—C16	1.5034 (15)	C2—C3	1.3948 (13)
C17—C18	1.5148 (13)	C2—C10	1.3945 (13)
C18—C19	1.5238 (12)	C3—C4	1.3905 (13)
C13—H12	0.951 (4)	C3—C7	1.3914 (12)
C14—H14	0.95 (3)	C4—C5	1.3878 (12)
C14—H13	0.951 (5)	C5—C6	1.3903 (12)
C15—H15	0.95 (2)	C7—C8	1.3889 (13)
C17—H16	0.951 (5)	C8—C9	1.3885 (13)
C17—H17	0.952 (11)	C9—C10	1.3885 (12)
C18—H19	0.950 (4)	C4—H2	0.951 (3)
C18—H18	0.951 (5)	C5—H3	0.951 (3)
C19—H21	0.949 (5)	C6—H1	0.950 (3)
C19—H20	0.950 (5)	C7—H4	0.951 (3)
C20—C21	1.5027 (15)	C8—H5	0.949 (3)
C21—C27	1.5379 (14)	C9—H6	0.950 (3)
C21—C22	1.5163 (14)	C10—H7	0.951 (4)
C22—C23	1.5234 (13)	C11—H8	0.952 (4)
C23—C24	1.5048 (14)	C11—H9	0.951 (5)
C23—C25	1.5336 (13)	C11—H10	0.951 (5)

C12—N1—C16	125.9 (4)	C21—C27—C26	112.11 (8)
C12—N1—H11	116.7 (5)	C20—C21—H23	106.2 (3)
C16—N1—H11	117.4 (3)	C22—C21—H23	111.7 (3)
C20—N2—C24	125.95 (10)	C27—C21—H23	108.6 (3)
C24—N2—H22	117.3 (3)	C21—C22—H24	110.9 (2)
C20—N2—H22	116.7 (3)	C21—C22—H25	111.2 (2)
O1—C12—N1	119.5 (5)	C23—C22—H24	108.8 (3)
N1—C12—C13	117.2 (6)	C23—C22—H25	111.5 (3)
O1—C12—C13	123.33 (18)	H24—C22—H25	106.3 (4)
C12—C13—C19	109.45 (9)	C22—C23—H26	111.7 (3)
C14—C13—C19	110.12 (8)	C24—C23—H26	105.0 (3)
C12—C13—C14	110.6 (2)	C25—C23—H26	109.2 (2)
C13—C14—C15	108.01 (8)	C23—C25—H27	104.8 (2)
C14—C15—C17	110.30 (8)	C23—C25—H28	107.1 (2)
C14—C15—C16	110.31 (8)	C26—C25—H27	109.9 (3)
C16—C15—C17	109.83 (8)	C26—C25—H28	112.4 (2)
O2—C16—C15	124.12 (16)	H27—C25—H28	109.5 (4)
N1—C16—C15	116.63 (10)	C25—C26—H29	109.4 (3)
O2—C16—N1	119.22 (16)	C25—C26—H30	110.3 (2)
C15—C17—C18	112.73 (7)	C27—C26—H29	107.0 (3)
C17—C18—C19	112.19 (7)	C27—C26—H30	109.2 (3)
C13—C19—C18	111.93 (8)	H29—C26—H30	108.3 (4)
C12—C13—H12	106.3 (4)	C21—C27—H31	108.3 (2)
C14—C13—H12	111.8 (3)	C21—C27—H32	106.8 (2)
C19—C13—H12	108.5 (2)	C26—C27—H31	112.8 (3)
C13—C14—H13	110.8 (3)	C26—C27—H32	111.7 (3)
H13—C14—H14	106 (3)	H31—C27—H32	104.6 (4)
C13—C14—H14	111 (3)	C2—C1—C6	119.67 (8)
C15—C14—H13	108.7 (3)	C2—C1—C11	120.36 (8)
C15—C14—H14	111.6 (18)	C6—C1—C11	119.97 (8)
C14—C15—H15	111.8 (3)	C1—C2—C3	119.99 (8)
C16—C15—H15	105.1 (13)	C1—C2—C10	120.25 (8)
C17—C15—H15	109.4 (11)	C3—C2—C10	119.72 (8)
C18—C17—H17	112.7 (11)	C2—C3—C4	120.05 (8)
H16—C17—H17	109.7 (7)	C2—C3—C7	119.89 (8)
C15—C17—H16	104.7 (2)	C4—C3—C7	120.05 (8)
C15—C17—H17	106.7 (17)	C3—C4—C5	119.91 (8)
C18—C17—H16	109.9 (3)	C4—C5—C6	120.10 (8)
C17—C18—H19	110.3 (3)	C1—C6—C5	120.26 (8)
H18—C18—H19	108.5 (4)	C3—C7—C8	120.15 (8)
C19—C18—H18	107.1 (3)	C7—C8—C9	120.02 (8)
C17—C18—H18	109.3 (3)	C8—C9—C10	120.09 (8)
C19—C18—H19	109.3 (2)	C2—C10—C9	120.11 (8)
C18—C19—H21	111.9 (3)	C3—C4—H2	120.1 (2)
H20—C19—H21	104.7 (4)	C5—C4—H2	120.0 (2)
C18—C19—H20	112.7 (2)	C4—C5—H3	119.9 (2)
C13—C19—H20	108.3 (3)	C6—C5—H3	120.0 (2)
C13—C19—H21	106.9 (2)	C1—C6—H1	119.9 (2)
O3—C20—N2	119.28 (14)	C5—C6—H1	119.9 (2)
N2—C20—C21	117.37 (10)	C3—C7—H4	120.0 (2)
O3—C20—C21	123.36 (14)	C8—C7—H4	119.9 (2)
C20—C21—C27	109.98 (9)	C7—C8—H5	120.0 (2)
C22—C21—C27	109.88 (7)	C9—C8—H5	120.0 (2)
C20—C21—C22	110.38 (9)	C8—C9—H6	119.9 (2)
C21—C22—C23	108.06 (8)	C10—C9—H6	120.0 (2)
C22—C23—C25	110.66 (8)	C2—C10—H7	120.0 (2)
C22—C23—C24	110.26 (8)	C9—C10—H7	119.9 (2)
C24—C23—C25	109.86 (9)	C1—C11—H8	109.3 (2)
O4—C24—C23	124.16 (15)	C1—C11—H9	109.7 (2)
N2—C24—C23	116.38 (9)	C1—C11—H10	109.6 (3)
O4—C24—N2	119.41 (15)	H8—C11—H9	109.5 (4)
C23—C25—C26	112.90 (7)	H8—C11—H10	109.4 (4)
C25—C26—C27	112.54 (8)	H9—C11—H10	109.3 (4)

C16—N1—C12—O1	−179.26 (18)	C22—C21—C27—C26	−57.27 (10)
C16—N1—C12—C13	−0.40 (18)	C21—C22—C23—C24	60.46 (11)
C12—N1—C16—O2	179.8 (7)	C21—C22—C23—C25	−61.29 (10)
C12—N1—C16—C15	1.51 (18)	C22—C23—C24—N2	−31.85 (15)
C20—N2—C24—O4	178.34 (19)	C25—C23—C24—O4	−87.1 (2)
C24—N2—C20—C21	0.9 (2)	C22—C23—C25—C26	54.33 (10)
C24—N2—C20—O3	−179.72 (18)	C24—C23—C25—C26	−67.65 (10)
C20—N2—C24—C23	0.7 (2)	C25—C23—C24—N2	90.38 (12)
O1—C12—C13—C14	−151.34 (18)	C22—C23—C24—O4	150.67 (19)
N1—C12—C13—C19	−91.62 (15)	C23—C25—C26—C27	−47.76 (10)
N1—C12—C13—C14	29.85 (14)	C25—C26—C27—C21	49.14 (10)
O1—C12—C13—C19	87.2 (2)	C6—C1—C2—C3	−0.3 (5)
C12—C13—C14—C15	−58.83 (16)	C6—C1—C2—C10	−178.0 (3)
C12—C13—C19—C18	64.9 (3)	C11—C1—C2—C3	179.3 (3)
C19—C13—C14—C15	62.25 (10)	C11—C1—C2—C10	1.7 (4)
C14—C13—C19—C18	−56.88 (11)	C2—C1—C6—C5	0.6 (4)
C13—C14—C15—C16	59.90 (10)	C11—C1—C6—C5	−179.1 (2)
C13—C14—C15—C17	−61.60 (10)	C1—C2—C3—C4	−0.8 (5)
C17—C15—C16—O2	−88.1 (7)	C1—C2—C3—C7	−179.4 (3)
C16—C15—C17—C18	−66.00 (10)	C10—C2—C3—C4	176.8 (3)
C14—C15—C17—C18	55.79 (10)	C10—C2—C3—C7	−1.8 (5)
C14—C15—C16—N1	−31.77 (13)	C1—C2—C10—C9	178.9 (3)
C14—C15—C16—O2	150.1 (7)	C3—C2—C10—C9	1.2 (5)
C17—C15—C16—N1	90.02 (11)	C2—C3—C4—C5	1.7 (5)
C15—C17—C18—C19	−49.32 (10)	C7—C3—C4—C5	−179.7 (3)
C17—C18—C19—C13	49.63 (10)	C2—C3—C7—C8	1.5 (5)
O3—C20—C21—C22	−150.43 (18)	C4—C3—C7—C8	−177.1 (3)
N2—C20—C21—C27	−92.44 (13)	C3—C4—C5—C6	−1.5 (5)
N2—C20—C21—C22	28.97 (14)	C4—C5—C6—C1	0.4 (4)
O3—C20—C21—C27	88.17 (19)	C3—C7—C8—C9	−0.6 (5)
C27—C21—C22—C23	62.69 (9)	C7—C8—C9—C10	0.0 (4)
C20—C21—C22—C23	−58.77 (10)	C8—C9—C10—C2	−0.3 (5)
C20—C21—C27—C26	64.43 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···O3	0.90 (1)	1.97 (1)	2.865 (2)	176 (1)
N2—H22···O2ⁱ	0.90 (1)	1.92 (1)	2.812 (8)	170 (1)

Symmetry code: (i) x, y+1, z.

Acknowledgements

We thank the Basic Technology Programme of the UK Research Councils for funding under the project Control and Prediction of the Organic Solid State (www.cposs.org.uk). We also thank the EPSRC for grant GR/N07462/01.

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