organic papers
o942
Li and Lin C23H23NO3 doi:10.1107/S1600536806003771 Acta Cryst.(2006). E62, o942–o944
Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
(
E
)-1-Ethoxycarbonyl-2-[(2-hydroxy-1-naphthyl)-(phenyl)methyliminio]propan-1-ide
Jing-Hua Li* and Chui-Pan Lin
College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310032, People’s Republic of China
Correspondence e-mail: lijh@zjut.edu.cn
Key indicators
Single-crystal X-ray study
T= 298 K
Mean(C–C) = 0.003 A˚
Rfactor = 0.049
wRfactor = 0.166
Data-to-parameter ratio = 17.7
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 16 January 2006 Accepted 31 January 2006
#2006 International Union of Crystallography All rights reserved
In the title compound, C23H23NO3, the amino, hydroxy and carbonyl groups are involved in hydrogen bonding, forming a dimer. The crystal packing is further stabilized by inter-molecular –stacking.
Comment
As early as the mid-20th century, Mario Betti reported the synthesis of the so-called Betti base by the reaction of benz-aldehyde with 2-naphthol and ammonia followed by hydro-lysis with hydrochloric acid (Betti, 1941). However, only in recent decades has its usefulness in asymmetric synthesis been recognized (Istvan et al., 2004). As cheap resolving agents, chiral catalysts and optically active ligands, the Betti base and its derivatives are now widely used in organic synthesis (Istvan et al., 2004). Chiral aminoalcohols are of importance in cata-lytic asymmetric synthesis (Pu et al., 2001). Compound (I), prepared readily from the Betti base by treatment with ethyl acetoacetate, is one of the auxiliary-induced prochiral imino compounds which yields the corresponding chiral amino-alcohol after asymmetric hydrogenation.
In the structure of (I), atoms N2, C18, C19 and C20 are coplanar; this is illustrated clearly by the torsion angle N2— C18—C19—C20 of 2.20 (2) (Fig. 1). Moreover, the mean
plane through these four atoms is perpendicular to the phenyl ring plane, forming a dihedral angle of 89.89 (9). The dihedral
angle between the naphthalene ring system and phenyl ring plane is 78.71 (6).
In the crystal structure, the amino, hydroxy and carbonyl groups are involved in hydrogen bonding. Amino atom N2 acts as hydrogen-bond donor,viaatom H201, to atom O31 and O32, forming intramolecular hydrogen bonds. A centrosym-metric hydrogen-bond dimer centred at (0,12,
1
2) is formed by the intermolecular hydrogen bond O31–H301 O32i [symmetry code: (i)x, 1y, 1z] (Table 2 and Fig. 2). The crystal packing is further stabilized by intermolecular –
another, the distance between the centroids of the rings being 3.898 A˚ .
Experimental
To Betti base {or 1-[amino(phenyl)methyl]naphthalen-2-ol} (1.0 g, 2.8 mmol), methanol (20 ml) and ethyl acetoacetate (1.5 ml) were added with stirring at room temperature. Stirring was continued for 3 h at the same temperature to complete the reaction. The resulting mixture was concentrated in vacuoto about 3 ml, and the precipi-tated crystals were collected by filtration and washed with methanol twice (20.8 ml) to give colourless crystals (1.41 g, yield 97%; m.p. 431–432 K), which were recrystallized from methanol.
Crystal data
C23H23NO3
Mr= 361.44
Triclinic,P1
a= 9.602 (4) A˚
b= 9.962 (5) A˚
c= 10.899 (5) A˚
= 100.775 (19)
= 109.714 (14)
= 93.722 (18)
V= 954.9 (7) A˚3
Z= 2
Dx= 1.257 Mg m
3
MoKradiation Cell parameters from 7862
reflections
= 3.1–27.6
= 0.08 mm1
T= 298 (1) K Chunk, colorless 0.300.240.18 mm
Data collection
Rigaku R-AXIS RAPID diffractometer
!scans
Absorption correction: none 9527 measured reflections 4346 independent reflections
3124 reflections withF2> 2(F2)
Rint= 0.023
max= 27.5
h=12!11
k=12!12
l=14!14
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.050
wR(F2) = 0.166
S= 1.00 4346 reflections 245 parameters
H-atom parameters constrained
w= 1/[0.0031Fo2+(Fo2)]/(4Fo2)
(/)max< 0.001
max= 0.29 e A˚
3
min=0.23 e A˚
3
Extinction correction: Larson (1970)
Extinction coefficient: 1.2 (4)102
Table 1
Selected bond lengths (A˚ ).
O31—C11 1.3624 (17)
O32—C20 1.235 (2)
O33—C20 1.350 (2)
O33—C21 1.429 (2)
N2—C1 1.4675 (16)
N2—C18 1.333 (2)
Table 2
Hydrogen-bond geometry (A˚ ,).
D—H A D—H H A D A D—H A
O31—H301 O32i
0.93 1.80 2.7182 (15) 170
N2—H201 O31 0.89 2.25 2.8182 (17) 122 N2—H201 O32 0.89 2.11 2.7634 (13) 129
Symmetry code: (i)x;yþ1;zþ1.
The H atoms of the amino group and hydroxy groups were located in difference Fourier maps and included in the refinement based on the as-found N—H and O—H bond lengths, but their isotropic displacement paramenters were initially refined, then fixed in the final stage. All other H atoms were placed in calculated positions, with C—H = 0.93–0.97 A˚ , and included in the refinement in the riding model, withUiso(H) = 1.2Ueq(carrier atom).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refine-ment:PROCESS-AUTO; data reduction:CrystalStructure(Rigaku/ MSC, 2004); program(s) used to solve structure:SHELXS97 (Shel-drick, 1997); program(s) used to refine structure: CRYSTALS (Betteridgeet al., 2003); molecular graphics:ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
References
[image:2.610.48.294.68.254.2]Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003).J. Appl. Cryst.36, 1487.
Figure 1
The molecular configuration and atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 40% probability level. H atoms
are drawn as spheres of arbitrary radius. Figure 2Partial packing digram for (I), showing the hydrogen-bonded (dashed
[image:2.610.314.562.73.265.2]Farrugia, L. J. (1997).J. Appl. Cryst.30, 565.
Istvan, S. & Ferenc, F. (2004).Curr. Org. Synth.1, 155–165.
Larson, A. C. (1970).Crystallographic Computing,edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard.
Pu, L. & Yu, H. B. (2001).Chem. Rev.101, 757–824.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, 3-9-12 Akishima, Tokyo 196-8666, Japan.
Rigaku/MSC (2004).CrystalStructure. Version 3.60. Rigaku/MSC, 9009 New Trails Drive, The Woodlands, TX 77381-5209, USA.
Sheldrick, G. M. (1997).SHELX97. University of Go¨ttingen, Germany.
organic papers
o944
Li and Lin Csupporting information
Acta Cryst. (2006). E62, o942–o944 [https://doi.org/10.1107/S1600536806003771]
(
E
)-1-Ethoxycarbonyl-2-[(2-hydroxy-1-naphthyl)(phenyl)methyliminio]propan-1-ide
Jing-Hua Li and Chui-Pan Lin
(E)-1-Ethoxycarbonyl-3-[(2-hydroxynaphthalen-1-ylmethyl)phenyliminio]butan-2-ide
Crystal data
C23H23NO3
Mr = 361.44 Triclinic, P1 Hall symbol: -P 1
a = 9.602 (4) Å
b = 9.962 (5) Å
c = 10.899 (5) Å
α = 100.775 (19)°
β = 109.714 (14)°
γ = 93.722 (18)°
V = 954.9 (7) Å3
Z = 2
F(000) = 384.00
Dx = 1.257 Mg m−3
Mo Kα radiation, λ = 0.71075 Å Cell parameters from 7862 reflections
θ = 3.1–27.6°
µ = 0.08 mm−1
T = 298 K Chunk, colorless 0.30 × 0.24 × 0.18 mm
Data collection
Rigaku R-AXIS RAPID diffractometer
Detector resolution: 10.00 pixels mm-1
ω scans
9527 measured reflections 4346 independent reflections
3124 reflections with F2 > 2σ(F2)
Rint = 0.023
θmax = 27.5°
h = −12→11
k = −12→12
l = −14→14
Refinement
Refinement on F2
R[F2 > 2σ(F2)] = 0.050
wR(F2) = 0.166
S = 1.00 4346 reflections 245 parameters
H-atom parameters constrained
w = 1/[0.0031Fo2 + σ(Fo2)]/(4Fo2)
(Δ/σ)max < 0.001
Δρmax = 0.29 e Å−3
Δρmin = −0.23 e Å−3
Extinction correction: Larson (1970) Extinction coefficient: 119 (38)
Special details
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R
-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
supporting information
sup-2 Acta Cryst. (2006). E62, o942–o944
O33 −0.06574 (13) 0.83611 (13) 0.24492 (12) 0.0661 (3) N2 0.24609 (12) 0.80909 (12) 0.61792 (12) 0.0398 (3) C1 0.36652 (12) 0.78535 (13) 0.73398 (13) 0.0355 (3) C2 0.42380 (13) 0.65073 (13) 0.69751 (12) 0.0341 (3) C3 0.57588 (13) 0.64680 (14) 0.70721 (13) 0.0376 (3) C4 0.68307 (16) 0.76502 (18) 0.74675 (17) 0.0483 (4)
C5 0.82626 (18) 0.7566 (2) 0.7505 (2) 0.0618 (5)
C6 0.87158 (18) 0.6273 (2) 0.7193 (2) 0.0624 (5)
C7 0.77362 (18) 0.5128 (2) 0.68143 (17) 0.0540 (4) C8 0.62282 (16) 0.51591 (17) 0.67392 (13) 0.0415 (3) C9 0.51910 (17) 0.39689 (16) 0.62937 (14) 0.0445 (4) C10 0.37352 (17) 0.40114 (14) 0.61832 (14) 0.0419 (3) C11 0.32730 (13) 0.53007 (14) 0.65342 (13) 0.0371 (3) C12 0.32249 (14) 0.79830 (14) 0.85641 (13) 0.0394 (3) C13 0.3810 (2) 0.7225 (2) 0.95251 (18) 0.0617 (5)
C14 0.3486 (3) 0.7423 (2) 1.0670 (2) 0.0842 (7)
C15 0.2541 (2) 0.8339 (3) 1.0872 (2) 0.0891 (7)
C16 0.1941 (2) 0.9058 (2) 0.9946 (2) 0.0810 (7)
C17 0.22885 (18) 0.8924 (2) 0.87835 (19) 0.0576 (4) C18 0.25072 (14) 0.90910 (13) 0.55280 (14) 0.0398 (3) C19 0.14278 (17) 0.91370 (16) 0.43419 (17) 0.0483 (4) C20 0.01721 (16) 0.81249 (16) 0.36429 (16) 0.0448 (4)
C21 −0.1872 (2) 0.7349 (2) 0.1551 (2) 0.0710 (5)
C22 −0.1341 (3) 0.6298 (3) 0.0722 (2) 0.0862 (9)
C23 0.3816 (2) 1.02309 (18) 0.6117 (2) 0.0619 (5)
H1 0.4492 0.8594 0.7561 0.040*
H4 0.6557 0.8513 0.7700 0.057*
H5 0.8939 0.8367 0.7754 0.071*
H6 0.9695 0.6222 0.7238 0.077*
H7 0.8046 0.4277 0.6605 0.068*
H9 0.5495 0.3118 0.6072 0.056*
H10 0.3060 0.3204 0.5881 0.050*
H13 0.4456 0.6602 0.9398 0.074*
H14 0.3889 0.6909 1.1303 0.100*
H15 0.2305 0.8456 1.1642 0.102*
H16 0.1308 0.9690 1.0086 0.091*
H17 0.1877 0.9439 0.8154 0.065*
H19 0.1530 0.9886 0.3967 0.057*
H201 0.1686 0.7417 0.5831 0.045*
H211 −0.2611 0.7793 0.0972 0.077*
H212 −0.2322 0.6899 0.2069 0.078*
H221 −0.2171 0.5780 −0.0032 0.103*
H222 −0.0842 0.5683 0.1252 0.103*
H223 −0.0657 0.6755 0.0413 0.103*
H231 0.3672 1.0912 0.5584 0.069*
H232 0.4716 0.9850 0.6140 0.069*
H233 0.3896 1.0653 0.7009 0.070*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O31 0.0361 (5) 0.0358 (5) 0.0649 (7) −0.0002 (4) 0.0212 (4) 0.0090 (5) O32 0.0430 (5) 0.0488 (6) 0.0568 (6) −0.0030 (4) 0.0077 (4) 0.0186 (5) O33 0.0670 (7) 0.0640 (8) 0.0522 (7) 0.0004 (6) −0.0021 (5) 0.0239 (6) N2 0.0342 (5) 0.0343 (6) 0.0449 (6) 0.0019 (4) 0.0062 (4) 0.0103 (5) C1 0.0292 (5) 0.0329 (7) 0.0406 (7) 0.0035 (4) 0.0087 (5) 0.0060 (5) C2 0.0333 (6) 0.0351 (7) 0.0345 (6) 0.0054 (5) 0.0124 (5) 0.0088 (5) C3 0.0337 (6) 0.0448 (8) 0.0344 (6) 0.0100 (5) 0.0109 (5) 0.0100 (5) C4 0.0344 (7) 0.0505 (9) 0.0574 (9) 0.0036 (6) 0.0140 (6) 0.0107 (7) C5 0.0341 (7) 0.0743 (12) 0.0709 (11) 0.0044 (7) 0.0141 (7) 0.0112 (10) C6 0.0355 (7) 0.0910 (14) 0.0653 (11) 0.0192 (8) 0.0199 (7) 0.0212 (10) C7 0.0456 (8) 0.0725 (11) 0.0502 (9) 0.0282 (8) 0.0202 (7) 0.0159 (8) C8 0.0417 (7) 0.0529 (9) 0.0352 (7) 0.0173 (6) 0.0158 (5) 0.0149 (6) C9 0.0556 (8) 0.0406 (8) 0.0419 (7) 0.0207 (6) 0.0193 (6) 0.0118 (6) C10 0.0506 (7) 0.0341 (7) 0.0422 (7) 0.0069 (5) 0.0170 (6) 0.0100 (6) C11 0.0361 (6) 0.0385 (7) 0.0374 (7) 0.0081 (5) 0.0134 (5) 0.0085 (5) C12 0.0335 (6) 0.0385 (7) 0.0385 (7) 0.0003 (5) 0.0087 (5) −0.0002 (5) C13 0.0819 (12) 0.0619 (11) 0.0416 (8) 0.0179 (9) 0.0213 (8) 0.0112 (8) C14 0.1155 (18) 0.0905 (17) 0.0439 (10) 0.0058 (14) 0.0280 (11) 0.0119 (10) C15 0.0825 (14) 0.121 (2) 0.0510 (11) −0.0230 (14) 0.0360 (10) −0.0218 (13) C16 0.0513 (10) 0.1112 (18) 0.0654 (13) 0.0098 (10) 0.0239 (9) −0.0223 (12) C17 0.0433 (7) 0.0670 (11) 0.0545 (9) 0.0133 (7) 0.0151 (7) −0.0030 (8) C18 0.0429 (7) 0.0290 (6) 0.0470 (7) 0.0042 (5) 0.0158 (6) 0.0085 (5) C19 0.0537 (8) 0.0370 (8) 0.0521 (9) 0.0037 (6) 0.0132 (7) 0.0166 (6) C20 0.0456 (7) 0.0431 (8) 0.0464 (8) 0.0114 (6) 0.0135 (6) 0.0154 (6) C21 0.0590 (10) 0.0826 (14) 0.0533 (10) −0.0027 (9) −0.0020 (8) 0.0176 (10) C22 0.073 (2) 0.097 (2) 0.0683 (15) −0.0077 (16) 0.0071 (14) 0.0108 (14) C23 0.0607 (10) 0.0432 (9) 0.0690 (11) −0.0107 (7) 0.0073 (8) 0.0177 (8)
Geometric parameters (Å, º)
O31—C11 1.3624 (17) C18—C23 1.510 (2)
O32—C20 1.235 (2) C19—C20 1.4092 (19)
O33—C20 1.350 (2) C21—C22 1.483 (4)
O33—C21 1.429 (2) O31—H301 0.929
N2—C1 1.4675 (16) N2—H201 0.893
N2—C18 1.333 (2) C1—H1 0.980
C1—C2 1.5175 (19) C4—H4 0.930
C1—C12 1.516 (2) C5—H5 0.930
C2—C3 1.4318 (19) C6—H6 0.930
C2—C11 1.3687 (18) C7—H7 0.930
C3—C4 1.409 (2) C9—H9 0.930
C3—C8 1.430 (2) C10—H10 0.930
C4—C5 1.370 (2) C13—H13 0.930
C5—C6 1.405 (3) C14—H14 0.930
supporting information
sup-4 Acta Cryst. (2006). E62, o942–o944
C7—C8 1.425 (2) C16—H16 0.930
C8—C9 1.392 (2) C17—H17 0.930
C9—C10 1.366 (2) C19—H19 0.930
C10—C11 1.413 (2) C21—H211 0.970
C12—C13 1.392 (2) C21—H212 0.970
C12—C17 1.384 (2) C22—H221 0.960
C13—C14 1.368 (3) C22—H222 0.960
C14—C15 1.368 (4) C22—H223 0.960
C15—C16 1.340 (3) C23—H231 0.960
C16—C17 1.400 (3) C23—H232 0.960
C18—C19 1.368 (2) C23—H233 0.960
O31···O32i 2.7182 (15) H10···C20i 3.531
O31···C6ii 3.490 (2) H10···C21i 3.477
O32···O31i 2.7182 (15) H10···C23xi 3.131
O32···C7iii 3.564 (2) H10···H14x 3.482
O32···C10i 3.443 (2) H10···H19xi 3.487
O32···C11i 3.5056 (17) H10···H212i 2.579
O33···C17iv 3.473 (2) H10···H231xi 2.385
C3···C9iii 3.402 (2) H10···H233xi 3.063
C6···O31v 3.490 (2) H13···C21vii 3.452
C6···C10iii 3.584 (2) H13···H211vii 2.798
C7···O32iii 3.564 (2) H13···H212vii 3.409
C7···C10iii 3.390 (2) H13···H221vii 3.275
C7···C11iii 3.379 (2) H13···H221i 3.448
C8···C9iii 3.424 (2) H14···C8x 3.254
C8···C10iii 3.447 (2) H14···C9x 2.793
C9···C3iii 3.402 (2) H14···C10x 3.247
C9···C8iii 3.424 (2) H14···C23viii 3.590
C10···O32i 3.443 (2) H14···H9x 2.726
C10···C6iii 3.584 (2) H14···H10x 3.482
C10···C7iii 3.390 (2) H14···H211vii 3.571
C10···C8iii 3.447 (2) H14···H212vii 3.448
C11···O32i 3.5056 (17) H14···H221i 2.884
C11···C7iii 3.379 (2) H14···H231viii 3.596
C17···O33iv 3.473 (2) H14···H233viii 2.970
O31···H6ii 2.619 H15···O33xii 3.249
O31···H7iii 3.425 H15···C19xii 3.291
O31···H201 2.247 H15···C20xii 3.500
O31···H212i 3.008 H15···H4viii 3.010
O31···H222i 3.302 H15···H5viii 3.481
O31···H301i 3.383 H15···H9x 3.387
O32···H6iii 3.479 H15···H19xii 3.011
O32···H7iii 2.750 H15···H223xii 2.951
O32···H10i 2.802 H15···H232viii 3.172
O32···H201 2.110 H15···H233viii 3.425
O32···H301i 1.799 H16···O33iv 3.576
O33···H16iv 3.576 H16···C5ii 3.515
O33···H17iv 2.638 H16···C5viii 3.313
O33···H233iv 3.522 H16···C16xiii 3.426
O33···H301i 3.562 H16···H4viii 2.794
N2···H7iii 3.345 H16···H5ii 2.798
N2···H201 0.893 H16···H5viii 2.842
C1···H201 2.005 H16···H16xiii 2.580
C2···H9iii 3.501 H16···H211iv 3.290
C2···H201 2.651 H16···H223xii 3.516
C3···H9iii 3.342 H17···O33iv 2.638
C3···H221vii 3.337 H17···C21iv 3.155
C4···H16viii 3.295 H17···H5ii 2.810
C4···H221vii 3.491 H17···H6ii 3.490
C5···H10iii 3.387 H17···H19iv 3.502
C5···H16v 3.515 H17···H201 2.870
C5···H16viii 3.313 H17···H211iv 2.705
C5···H19ix 3.275 H19···C5ix 3.275
C5···H223vii 3.259 H19···H4ix 3.489
C6···H10iii 3.364 H19···H5ix 2.738
C6···H221vii 3.514 H19···H10xv 3.487
C6···H222iii 3.202 H19···H15vi 3.011
C6···H223vii 3.288 H19···H17iv 3.502
C6···H301v 3.484 H19···H201 3.452
C7···H10iii 3.528 H201···O31 2.247
C7···H221vii 3.346 H201···O32 2.110
C7···H222iii 3.271 H201···N2 0.893
C8···H14x 3.254 H201···C1 2.005
C8···H221vii 3.247 H201···C2 2.651
C9···H14x 2.793 H201···C11 2.754
C9···H231xi 3.128 H201···C12 2.769
C10···H14x 3.247 H201···C17 3.125
C10···H212i 2.919 H201···C18 1.930
C10···H231xi 3.026 H201···C19 2.541
C11···H7iii 3.343 H201···C20 2.593
C11···H201 2.754 H201···C23 3.262
C11···H212i 3.143 H201···H1 2.743
C12···H6ii 3.410 H201···H6ii 3.128
C12···H201 2.769 H201···H7iii 2.968
C13···H211vii 3.221 H201···H17 2.870
C13···H221i 3.513 H201···H19 3.452
C14···H9x 3.507 H201···H232 3.546
C14···H221i 3.212 H201···H233 3.503
C14···H233viii 3.108 H201···H301 3.020
C15···H4viii 3.150 H201···H301i 3.175
C15···H223xii 3.194 H211···C13xiv 3.221
C15···H232viii 3.493 H211···C16iv 3.549
C15···H233viii 3.377 H211···C17iv 3.217
supporting information
sup-6 Acta Cryst. (2006). E62, o942–o944
C16···H5ii 2.995 H211···H14xiv 3.571
C16···H5viii 3.589 H211···H16iv 3.290
C16···H16xiii 3.426 H211···H17iv 2.705
C16···H211iv 3.549 H211···H233iv 3.093
C16···H223xii 3.507 H212···O31i 3.008
C17···H5ii 3.002 H212···C10i 2.919
C17···H6ii 3.300 H212···C11i 3.143
C17···H201 3.125 H212···H10i 2.579
C17···H211iv 3.217 H212···H13xiv 3.409
C18···H9iii 3.596 H212···H14xiv 3.448
C18···H201 1.930 H212···H233iv 3.135
C19···H7iii 3.486 H212···H301i 2.543
C19···H15vi 3.291 H221···C3xiv 3.337
C19···H201 2.541 H221···C4xiv 3.491
C20···H7iii 3.054 H221···C6xiv 3.514
C20···H10i 3.531 H221···C7xiv 3.346
C20···H15vi 3.500 H221···C8xiv 3.247
C20···H201 2.593 H221···C13i 3.513
C20···H301i 2.953 H221···C14i 3.212
C21···H13xiv 3.452 H221···H13xiv 3.275
C21···H17iv 3.155 H221···H13i 3.448
C21···H233iv 3.405 H221···H14i 2.884
C21···H301i 3.275 H222···O31i 3.302
C22···H301i 3.598 H222···C6iii 3.202
C23···H9xv 3.221 H222···C7iii 3.271
C23···H10xv 3.131 H222···H6iii 2.782
C23···H14viii 3.590 H222···H7iii 2.896
C23···H201 3.262 H222···H223xvi 3.439
C23···H232ix 3.213 H222···H301i 3.010
H1···H201 2.743 H223···C5xiv 3.259
H4···C15viii 3.150 H223···C6xiv 3.288
H4···C16viii 3.041 H223···C15vi 3.194
H4···H15viii 3.010 H223···C16vi 3.507
H4···H16viii 2.794 H223···H5xiv 3.492
H4···H19ix 3.489 H223···H6xiv 3.534
H5···C16v 2.995 H223···H15vi 2.951
H5···C16viii 3.589 H223···H16vi 3.516
H5···C17v 3.002 H223···H222xvi 3.439
H5···H15viii 3.481 H231···C9xv 3.128
H5···H16v 2.798 H231···C10xv 3.026
H5···H16viii 2.842 H231···H9xv 2.572
H5···H17v 2.810 H231···H10xv 2.385
H5···H19ix 2.738 H231···H14viii 3.596
H5···H223vii 3.492 H231···H232ix 2.844
H6···O31v 2.619 H232···C15viii 3.493
H6···O32iii 3.479 H232···C23ix 3.213
H6···C12v 3.410 H232···H9xv 3.313
H6···H17v 3.490 H232···H15viii 3.172
H6···H201v 3.128 H232···H201 3.546
H6···H222iii 2.782 H232···H231ix 2.844
H6···H223vii 3.534 H232···H232ix 2.781
H6···H301v 2.726 H233···O33iv 3.522
H6···H301iii 3.434 H233···C14viii 3.108
H7···O31iii 3.425 H233···C15viii 3.377
H7···O32iii 2.750 H233···C21iv 3.405
H7···N2iii 3.345 H233···H9xv 3.307
H7···C11iii 3.343 H233···H10xv 3.063
H7···C19iii 3.486 H233···H14viii 2.970
H7···C20iii 3.054 H233···H15viii 3.425
H7···H201iii 2.968 H233···H201 3.503
H7···H222iii 2.896 H233···H211iv 3.093
H7···H301v 3.299 H233···H212iv 3.135
H9···C2iii 3.501 H301···O31i 3.383
H9···C3iii 3.342 H301···O32i 1.799
H9···C14x 3.507 H301···O33i 3.562
H9···C18iii 3.596 H301···C6ii 3.484
H9···C23xi 3.221 H301···C20i 2.953
H9···H14x 2.726 H301···C21i 3.275
H9···H15x 3.387 H301···C22i 3.598
H9···H231xi 2.572 H301···H6ii 2.726
H9···H232xi 3.313 H301···H6iii 3.434
H9···H232iii 3.395 H301···H7ii 3.299
H9···H233xi 3.307 H301···H201 3.020
H10···O32i 2.802 H301···H201i 3.175
H10···C5iii 3.387 H301···H212i 2.543
H10···C6iii 3.364 H301···H222i 3.010
H10···C7iii 3.528 H301···H301i 3.270
C20—O33—C21 119.63 (15) C2—C1—H1 106.7
C1—N2—C18 126.54 (10) C12—C1—H1 106.3
N2—C1—C2 110.49 (10) C3—C4—H4 119.2
N2—C1—C12 112.19 (11) C5—C4—H4 119.0
C2—C1—C12 114.04 (12) C4—C5—H5 119.8
C1—C2—C3 121.71 (11) C6—C5—H5 120.1
C1—C2—C11 119.12 (12) C5—C6—H6 119.7
C3—C2—C11 119.17 (13) C7—C6—H6 120.4
C2—C3—C4 123.87 (13) C6—C7—H7 119.3
C2—C3—C8 118.64 (12) C8—C7—H7 118.5
C4—C3—C8 117.49 (13) C8—C9—H9 119.4
C3—C4—C5 121.84 (16) C10—C9—H9 118.8
C4—C5—C6 120.10 (17) C9—C10—H10 120.4
C5—C6—C7 119.93 (17) C11—C10—H10 120.6
C6—C7—C8 122.18 (18) C12—C13—H13 119.3
C3—C8—C7 118.41 (14) C14—C13—H13 120.0
supporting information
sup-8 Acta Cryst. (2006). E62, o942–o944
C7—C8—C9 122.14 (15) C15—C14—H14 119.9
C8—C9—C10 121.84 (14) C14—C15—H15 120.3
C9—C10—C11 118.95 (13) C16—C15—H15 120.0
O31—C11—C2 117.91 (13) C15—C16—H16 119.8
O31—C11—C10 120.10 (12) C17—C16—H16 118.6
C2—C11—C10 121.99 (13) C12—C17—H17 120.2
C1—C12—C13 121.32 (15) C16—C17—H17 120.8
C1—C12—C17 120.11 (15) C18—C19—H19 117.8
C13—C12—C17 118.48 (17) C20—C19—H19 117.6
C12—C13—C14 120.7 (2) O33—C21—H211 109.6
C13—C14—C15 120.5 (2) O33—C21—H212 108.7
C14—C15—C16 119.7 (2) C22—C21—H211 109.2
C15—C16—C17 121.6 (2) C22—C21—H212 109.0
C12—C17—C16 119.00 (19) H211—C21—H212 109.5
N2—C18—C19 123.32 (12) C21—C22—H221 110.1
N2—C18—C23 118.79 (12) C21—C22—H222 109.4
C19—C18—C23 117.89 (15) C21—C22—H223 108.9
C18—C19—C20 124.60 (16) H221—C22—H222 109.4
O32—C20—O33 121.65 (12) H221—C22—H223 109.5
O32—C20—C19 125.62 (14) H222—C22—H223 109.5
O33—C20—C19 112.73 (15) C18—C23—H231 110.0
O33—C21—C22 110.74 (18) C18—C23—H232 109.4
C11—O31—H301 110.8 C18—C23—H233 109.0
C1—N2—H201 114.1 H231—C23—H232 109.5
C18—N2—H201 118.8 H231—C23—H233 109.5
N2—C1—H1 106.5 H232—C23—H233 109.5
C20—O33—C21—C22 −85.7 (2) C4—C3—C8—C7 −0.6 (2)
C21—O33—C20—O32 −7.0 (2) C4—C3—C8—C9 −177.53 (15)
C21—O33—C20—C19 172.89 (16) C8—C3—C4—C5 1.5 (2)
C1—N2—C18—C19 170.30 (15) C3—C4—C5—C6 −2.4 (3)
C1—N2—C18—C23 −9.3 (2) C4—C5—C6—C7 2.4 (3)
C18—N2—C1—C2 −113.44 (16) C5—C6—C7—C8 −1.5 (3)
C18—N2—C1—C12 118.09 (16) C6—C7—C8—C3 0.6 (2)
N2—C1—C2—C3 119.32 (14) C6—C7—C8—C9 177.45 (18)
N2—C1—C2—C11 −60.26 (18) C3—C8—C9—C10 −1.0 (2)
N2—C1—C12—C13 149.65 (13) C7—C8—C9—C10 −177.85 (16)
N2—C1—C12—C17 −33.99 (16) C8—C9—C10—C11 −0.1 (2)
C2—C1—C12—C13 23.07 (16) C9—C10—C11—O31 179.47 (14)
C2—C1—C12—C17 −160.57 (11) C9—C10—C11—C2 0.3 (2)
C12—C1—C2—C3 −113.21 (14) C1—C12—C13—C14 175.34 (16)
C12—C1—C2—C11 67.20 (15) C1—C12—C17—C16 −177.75 (14)
C1—C2—C3—C4 −1.9 (2) C13—C12—C17—C16 −1.3 (2)
C1—C2—C3—C8 178.66 (13) C17—C12—C13—C14 −1.1 (2)
C1—C2—C11—O31 1.1 (2) C12—C13—C14—C15 2.2 (3)
C1—C2—C11—C10 −179.75 (14) C13—C14—C15—C16 −0.8 (3)
C3—C2—C11—O31 −178.53 (13) C14—C15—C16—C17 −1.7 (3)
C11—C2—C3—C4 177.66 (15) N2—C18—C19—C20 −2.2 (2)
C11—C2—C3—C8 −1.7 (2) C23—C18—C19—C20 177.45 (17)
C2—C3—C4—C5 −177.89 (17) C18—C19—C20—O32 4.8 (3)
C2—C3—C8—C7 178.89 (14) C18—C19—C20—O33 −175.09 (16)
C2—C3—C8—C9 1.9 (2)
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1; (iv) −x, −y+2, −z+1; (v) x+1, y, z; (vi) x, y, z−1; (vii) x+1, y, z+1; (viii) −x+1, −y+2, −z+2; (ix) −x+1, −y+2, −z+1; (x) −x+1, −y+1, −z+2; (xi) x, y−1, z; (xii) x, y, z+1; (xiii) −x, −y+2, −z+2; (xiv) x−1, y, z−1; (xv) x, y+1, z; (xvi) −x, −y+1, −z.
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O31—H301···O32i 0.93 1.80 2.7182 (15) 170
N2—H201···O31 0.89 2.25 2.8182 (17) 122
N2—H201···O32 0.89 2.11 2.7634 (13) 129