organic papers
Acta Cryst.(2004). E60, o2223±o2224 doi: 10.1107/S1600536804027539 Hemmige S. Yathirajanet al. C23H31NO7
o2223
Acta Crystallographica Section EStructure Reports
Online
ISSN 1600-5368
Mycophenolate mofetil
Hemmige S. Yathirajan,a
Basavegowda Nagaraj,a
Santhosh L. Gaonkar,a
Rajenahally S. Narasegowda,a
Padmarajaiah Nagarajaaand
Michael Bolteb*
aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, andbInstitut fuÈr Anorganische Chemie, J. W. Goethe-UniversitaÈt Frankfurt, Marie-Curie-Straûe 11, 60439 Frankfurt/Main, Germany
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 173 K
Mean(C±C) = 0.002 AÊ
Rfactor = 0.043
wRfactor = 0.118
Data-to-parameter ratio = 18.2
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved
The title compound, morpholinoethyl (E
)-6-(1,3-dihydro- 4-hydroxy-6-methoxy-7-methyl-3-oxo-2-benzofuran-5-yl)-4-methylhex-4-enoate, C23H31NO7, belongs to the group of immunosuppresant drugs. Its crystal structure is stabilized by
OÐH O and CÐH O hydrogen bonds.
Comment
The crystal structure of sodium mycophenolate has been
reported by Rihs et al. (2000). We report here the crystal
structure of morpholinoethyl (E
)-6-(1,3-dihydro-4-hydroxy-6- methoxy-7-methyl-3-oxo-2-benzofuran-5-yl)-4-methylhex-4-enoate, (I), or mycophenolate mofetil, which is the mofetil ester of myophenolic acid, the active immunosuppresant (Moder, 2003). Mycophenolate mofetil is an active ingredient for immunosuppresant drugs used to prevent the body from rejecting a transplanted organ. Mycophenolate acts by blocking the action of a compound called inosine monophosphate dehydrogenase, which is required for the production of certain blood cells called T- and B-lymphocytes (Allison & Eugui, 1996).
A perspective view of (I) is shown in Fig. 1. Bond lengths and angles can be regarded as normal (Cambridge Structural Database, Version 1.6 plus three updates; Mogul Version 1.0; Allen, 2002). The morpholine ring adopts a chair conform-ation.
Experimental
The title compound was obtained as a gift from Thykn International (India). It was recrystallized from methanol to give colourless plates.
Crystal data C23H31NO7 Mr= 433.49
Monoclinic,P21=c a= 20.784 (2) AÊ
b= 9.3210 (6) AÊ
c= 11.9373 (11) AÊ
= 106.719 (7)
V= 2214.8 (3) AÊ3 Z= 4
Dx= 1.300 Mg mÿ3
MoKradiation
Cell parameters from 20 060 re¯ections
= 3.6±27.2
= 0.10 mmÿ1 T= 173 (2) K Plate, colourless 0.420.360.22 mm
Data collection Stoe IPDS-II two-circle
diffractometer
!scans
Absorption correction: none 30 508 measured re¯ections 5213 independent re¯ections
3770 re¯ections withI> 2(I)
Rint= 0.063
max= 27.9 h=ÿ27!27
k=ÿ12!12
l=ÿ15!15
Refinement Re®nement onF2 R[F2> 2(F2)] = 0.043 wR(F2) = 0.118 S= 0.97 5213 re¯ections 287 parameters
H atoms treated by a mixture of independent and constrained re®nement
w= 1/[2(F
o2) + (0.078P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.77 e AÊÿ3
min=ÿ0.45 e AÊÿ3
Table 1
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
O16ÐH16 O19 0.85 (2) 2.42 (2) 3.0717 (15) 134 (2) O16ÐH16 O24i 0.85 (2) 2.07 (2) 2.7664 (15) 139 (2)
C17ÐH17B O19ii 0.99 2.37 3.3205 (17) 162
C22ÐH22B O61iii 0.99 2.54 3.497 (3) 163 Symmetry codes: (i) 1ÿx;yÿ1
2;32ÿz; (ii)x;12ÿy;zÿ12; (iii)x;32ÿy;zÿ12.
H atoms bonded to C atoms were re®ned with ®xed individual displacement parameters [Uiso(H) = 1.2Ueq(C)] using a riding model,
with CÐH = 0.99, 0.98 and 0.95 AÊ for secondary CH, methyl and aromatic CH, respectively. The methyl groups were allowed to rotate but not to tip. The hydroxyl H atom was re®ned isotropically.
Data collection: X-AREA (Stoe & Cie, 2001); cell re®nement:
X-AREA; data reduction: X-AREA; program(s) used to solve structure:SHELXS97 (Sheldrick, 1990); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics:XPin
SHELXTL-Plus(Sheldrick, 1991); software used to prepare material for publication:SHELXL97 andPLATON(Spek, 2003).
One of the authors (HSY) thanks Thykn International (India), Mumbai, for a gift sample of mycophenolate mofetil.
References
Allen, F. H. (2002).Acta Cryst.B58, 380±388.
Allison, A. C. & Eugui, E. M. (1996).Clin. Transplant,10, 77±84. Moder, K. G. (2003).Ann. Allergy Asthma Immunol.90, 15±20. Rihs, G., Papageorgiou, C. & Pfeffer, S. (2000).Acta Cryst.C56, 432±433. Sheldrick, G. M. (1990).Acta Cryst.A46, 467±473.
Sheldrick, G. M. (1991).SHELXTL-Plus.Release 4.1. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (1997).SHELXL97. University of GoÈttingen, Germany. Spek, A. L. (2003).J. Appl. Cryst.36, 7±13.
Stoe & Cie (2001).X-AREA. Stoe & Cie, Darmstadt, Germany.
Figure 1
supporting information
sup-1 Acta Cryst. (2004). E60, o2223–o2224
supporting information
Acta Cryst. (2004). E60, o2223–o2224 [https://doi.org/10.1107/S1600536804027539]
Mycophenolate mofetil
Hemmige S. Yathirajan, Basavegowda Nagaraj, Santhosh L. Gaonkar, Rajenahally S.
Narasegowda, Padmarajaiah Nagaraja and Michael Bolte
Morpholinoethyl 6-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-2-benzofuran-5-yl)-
4-methylhex-4-enoate
Crystal data
C23H31NO7 Mr = 433.49 Monoclinic, P21/c Hall symbol: -P 2ybc a = 20.784 (2) Å b = 9.3210 (6) Å c = 11.9373 (11) Å β = 106.719 (7)° V = 2214.8 (3) Å3 Z = 4
F(000) = 928 Dx = 1.300 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 20060 reflections θ = 3.6–27.2°
µ = 0.10 mm−1 T = 173 K Plate, colourless 0.42 × 0.36 × 0.22 mm
Data collection
Stoe IPDS-II two-circle diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
30508 measured reflections 5213 independent reflections
3770 reflections with I > 2σ(I) Rint = 0.063
θmax = 27.9°, θmin = 3.6° h = −27→27
k = −12→12 l = −15→15
Refinement
Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.043 wR(F2) = 0.118 S = 0.97 5213 reflections 287 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ2(Fo2) + (0.078P)2] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001
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. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
C1 0.21914 (6) 0.72031 (15) 0.73294 (12) 0.0310 (3)
H1A 0.2102 0.7149 0.8100 0.037*
H1B 0.2140 0.8216 0.7069 0.037*
C2 0.29039 (6) 0.67204 (15) 0.74582 (12) 0.0307 (3)
H2 0.3020 0.6549 0.6756 0.037*
C3 0.33827 (7) 0.65131 (15) 0.84555 (12) 0.0319 (3)
C31 0.32775 (8) 0.6741 (2) 0.96380 (13) 0.0428 (4)
H31A 0.3390 0.7734 0.9889 0.064*
H31B 0.3567 0.6084 1.0205 0.064*
H31C 0.2806 0.6553 0.9591 0.064*
C4 0.40887 (7) 0.60491 (17) 0.85139 (13) 0.0358 (3)
H4A 0.4407 0.6760 0.8986 0.043*
H4B 0.4179 0.5120 0.8931 0.043*
C5 0.42319 (7) 0.5886 (2) 0.73489 (14) 0.0431 (4)
H5A 0.3941 0.5119 0.6896 0.052*
H5B 0.4115 0.6792 0.6904 0.052*
C6 0.49534 (8) 0.5526 (2) 0.74653 (15) 0.0459 (4)
O61 0.54019 (7) 0.5477 (3) 0.83489 (14) 0.0972 (7)
O7 0.50465 (6) 0.53661 (17) 0.64248 (11) 0.0566 (4)
C8 0.57230 (8) 0.5151 (2) 0.63496 (17) 0.0481 (4)
H8A 0.5721 0.4430 0.5740 0.058*
H8B 0.6015 0.4794 0.7107 0.058*
C9 0.59862 (8) 0.65635 (19) 0.60480 (16) 0.0449 (4)
H9A 0.5631 0.7044 0.5428 0.054*
H9B 0.6099 0.7191 0.6746 0.054*
C11 0.16846 (6) 0.62932 (14) 0.64612 (11) 0.0259 (3)
C12 0.13834 (6) 0.67517 (14) 0.53124 (12) 0.0266 (3)
O12 0.15805 (5) 0.80533 (10) 0.49810 (9) 0.0327 (2)
C12′ 0.11303 (8) 0.92150 (16) 0.49909 (16) 0.0413 (4)
H12A 0.0678 0.8966 0.4504 0.062*
H12B 0.1285 1.0081 0.4681 0.062*
H12C 0.1120 0.9392 0.5795 0.062*
C13 0.09289 (6) 0.59210 (14) 0.44591 (11) 0.0268 (3)
C13′ 0.06382 (7) 0.64163 (17) 0.32189 (12) 0.0341 (3)
supporting information
sup-3 Acta Cryst. (2004). E60, o2223–o2224
H13B 0.0952 0.7082 0.3014 0.051*
H13C 0.0210 0.6904 0.3141 0.051*
C14 0.07939 (6) 0.45816 (14) 0.48251 (11) 0.0256 (3)
C15 0.10803 (6) 0.40935 (13) 0.59536 (11) 0.0254 (2)
C16 0.15297 (6) 0.49251 (14) 0.67874 (11) 0.0261 (3)
O16 0.18282 (5) 0.44898 (12) 0.78920 (8) 0.0340 (2)
H16 0.1759 (11) 0.361 (3) 0.799 (2) 0.061 (6)*
C17 0.03747 (7) 0.33941 (15) 0.41517 (12) 0.0302 (3)
H17A −0.0100 0.3698 0.3839 0.036*
H17B 0.0543 0.3091 0.3492 0.036*
O18 0.04378 (5) 0.22420 (10) 0.49888 (9) 0.0332 (2)
C19 0.08544 (6) 0.26392 (14) 0.60427 (12) 0.0286 (3)
O19 0.09833 (5) 0.18398 (11) 0.68731 (9) 0.0380 (2)
N21 0.65803 (6) 0.63762 (14) 0.56474 (11) 0.0371 (3)
C22 0.67696 (8) 0.7741 (2) 0.52345 (16) 0.0467 (4)
H22A 0.6857 0.8457 0.5874 0.056*
H22B 0.6395 0.8100 0.4578 0.056*
C23 0.73892 (9) 0.7564 (2) 0.48328 (15) 0.0506 (4)
H23A 0.7292 0.6890 0.4164 0.061*
H23B 0.7512 0.8501 0.4562 0.061*
O24 0.79382 (5) 0.70349 (12) 0.57480 (10) 0.0413 (3)
C25 0.77590 (7) 0.56914 (16) 0.61392 (16) 0.0409 (4)
H25A 0.8140 0.5321 0.6778 0.049*
H25B 0.7665 0.4993 0.5487 0.049*
C26 0.71484 (7) 0.58344 (17) 0.65732 (14) 0.0357 (3)
H26A 0.7034 0.4887 0.6839 0.043*
H26B 0.7248 0.6499 0.7248 0.043*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C14 0.0210 (5) 0.0323 (6) 0.0242 (6) 0.0025 (5) 0.0075 (5) −0.0031 (5) C15 0.0237 (6) 0.0282 (6) 0.0256 (6) 0.0022 (4) 0.0090 (5) −0.0014 (5) C16 0.0232 (5) 0.0316 (6) 0.0235 (6) 0.0037 (4) 0.0068 (5) −0.0013 (5) O16 0.0373 (5) 0.0364 (5) 0.0240 (5) 0.0006 (4) 0.0022 (4) 0.0018 (4) C17 0.0275 (6) 0.0354 (7) 0.0273 (7) −0.0005 (5) 0.0072 (5) −0.0046 (5) O18 0.0323 (5) 0.0321 (5) 0.0342 (5) −0.0037 (4) 0.0079 (4) −0.0052 (4) C19 0.0270 (6) 0.0309 (6) 0.0299 (7) 0.0008 (5) 0.0113 (5) −0.0030 (5) O19 0.0438 (6) 0.0333 (5) 0.0382 (6) 0.0003 (4) 0.0141 (5) 0.0042 (4) N21 0.0269 (6) 0.0461 (7) 0.0374 (7) 0.0026 (5) 0.0078 (5) −0.0003 (5) C22 0.0379 (8) 0.0524 (9) 0.0442 (9) 0.0029 (7) 0.0026 (7) 0.0116 (7) C23 0.0475 (9) 0.0680 (11) 0.0347 (9) −0.0116 (8) 0.0093 (7) 0.0018 (8) O24 0.0334 (5) 0.0504 (6) 0.0416 (6) −0.0052 (4) 0.0131 (5) −0.0067 (5) C25 0.0297 (7) 0.0386 (8) 0.0567 (10) −0.0001 (5) 0.0159 (7) −0.0105 (7) C26 0.0283 (6) 0.0390 (7) 0.0398 (8) 0.0054 (5) 0.0095 (6) −0.0001 (6)
Geometric parameters (Å, º)
C1—C11 1.5083 (17) C12′—H12B 0.9800
C1—C2 1.5126 (18) C12′—H12C 0.9800
C1—H1A 0.9900 C13—C14 1.3779 (19)
C1—H1B 0.9900 C13—C13′ 1.5018 (18)
C2—C3 1.328 (2) C13′—H13A 0.9800
C2—H2 0.9500 C13′—H13B 0.9800
C3—C31 1.504 (2) C13′—H13C 0.9800
C3—C4 1.5121 (19) C14—C15 1.3838 (18)
C31—H31A 0.9800 C14—C17 1.4924 (18)
C31—H31B 0.9800 C15—C16 1.3889 (18)
C31—H31C 0.9800 C15—C19 1.4485 (18)
C4—C5 1.511 (2) C16—O16 1.3482 (16)
C4—H4A 0.9900 O16—H16 0.85 (2)
C4—H4B 0.9900 C17—O18 1.4469 (17)
C5—C6 1.504 (2) C17—H17A 0.9900
C5—H5A 0.9900 C17—H17B 0.9900
C5—H5B 0.9900 O18—C19 1.3574 (17)
C6—O61 1.191 (2) C19—O19 1.2070 (17)
C6—O7 1.319 (2) N21—C26 1.4560 (19)
O7—C8 1.4483 (18) N21—C22 1.459 (2)
C8—C9 1.508 (3) C22—C23 1.507 (2)
C8—H8A 0.9900 C22—H22A 0.9900
C8—H8B 0.9900 C22—H22B 0.9900
C9—N21 1.4573 (18) C23—O24 1.422 (2)
C9—H9A 0.9900 C23—H23A 0.9900
C9—H9B 0.9900 C23—H23B 0.9900
C11—C16 1.3977 (18) O24—C25 1.423 (2)
C11—C12 1.4004 (19) C25—C26 1.5083 (19)
C12—O12 1.3745 (16) C25—H25A 0.9900
C12—C13 1.4057 (19) C25—H25B 0.9900
supporting information
sup-5 Acta Cryst. (2004). E60, o2223–o2224
C12′—H12A 0.9800 C26—H26B 0.9900
C11—C1—C2 111.86 (11) H12B—C12′—H12C 109.5
C11—C1—H1A 109.2 C14—C13—C12 115.16 (11)
C2—C1—H1A 109.2 C14—C13—C13′ 122.02 (12)
C11—C1—H1B 109.2 C12—C13—C13′ 122.74 (12)
C2—C1—H1B 109.2 C13—C13′—H13A 109.5
H1A—C1—H1B 107.9 C13—C13′—H13B 109.5
C3—C2—C1 126.41 (13) H13A—C13′—H13B 109.5
C3—C2—H2 116.8 C13—C13′—H13C 109.5
C1—C2—H2 116.8 H13A—C13′—H13C 109.5
C2—C3—C31 123.16 (13) H13B—C13′—H13C 109.5
C2—C3—C4 123.37 (13) C13—C14—C15 122.46 (12)
C31—C3—C4 113.47 (12) C13—C14—C17 129.93 (12)
C3—C31—H31A 109.5 C15—C14—C17 107.54 (11)
C3—C31—H31B 109.5 C14—C15—C16 121.77 (12)
H31A—C31—H31B 109.5 C14—C15—C19 108.75 (11)
C3—C31—H31C 109.5 C16—C15—C19 129.42 (12)
H31A—C31—H31C 109.5 O16—C16—C15 123.94 (12)
H31B—C31—H31C 109.5 O16—C16—C11 117.97 (12)
C5—C4—C3 115.58 (12) C15—C16—C11 118.09 (12)
C5—C4—H4A 108.4 C16—O16—H16 112.1 (16)
C3—C4—H4A 108.4 O18—C17—C14 104.81 (10)
C5—C4—H4B 108.4 O18—C17—H17A 110.8
C3—C4—H4B 108.4 C14—C17—H17A 110.8
H4A—C4—H4B 107.4 O18—C17—H17B 110.8
C6—C5—C4 113.12 (13) C14—C17—H17B 110.8
C6—C5—H5A 109.0 H17A—C17—H17B 108.9
C4—C5—H5A 109.0 C19—O18—C17 110.15 (10)
C6—C5—H5B 109.0 O19—C19—O18 121.63 (12)
C4—C5—H5B 109.0 O19—C19—C15 129.64 (13)
H5A—C5—H5B 107.8 O18—C19—C15 108.73 (11)
O61—C6—O7 122.69 (15) C26—N21—C9 111.78 (12)
O61—C6—C5 126.60 (16) C26—N21—C22 108.68 (12)
O7—C6—C5 110.53 (14) C9—N21—C22 110.04 (13)
C6—O7—C8 118.81 (14) N21—C22—C23 110.49 (14)
O7—C8—C9 108.62 (14) N21—C22—H22A 109.6
O7—C8—H8A 110.0 C23—C22—H22A 109.6
C9—C8—H8A 110.0 N21—C22—H22B 109.6
O7—C8—H8B 110.0 C23—C22—H22B 109.6
C9—C8—H8B 110.0 H22A—C22—H22B 108.1
H8A—C8—H8B 108.3 O24—C23—C22 111.34 (13)
N21—C9—C8 111.94 (13) O24—C23—H23A 109.4
N21—C9—H9A 109.2 C22—C23—H23A 109.4
C8—C9—H9A 109.2 O24—C23—H23B 109.4
N21—C9—H9B 109.2 C22—C23—H23B 109.4
C8—C9—H9B 109.2 H23A—C23—H23B 108.0
C16—C11—C12 118.51 (12) O24—C25—C26 111.13 (12)
C16—C11—C1 119.53 (12) O24—C25—H25A 109.4
C12—C11—C1 121.89 (12) C26—C25—H25A 109.4
O12—C12—C11 117.71 (12) O24—C25—H25B 109.4
O12—C12—C13 118.13 (12) C26—C25—H25B 109.4
C11—C12—C13 124.01 (12) H25A—C25—H25B 108.0
C12—O12—C12′ 114.52 (10) N21—C26—C25 110.41 (13)
O12—C12′—H12A 109.5 N21—C26—H26A 109.6
O12—C12′—H12B 109.5 C25—C26—H26A 109.6
H12A—C12′—H12B 109.5 N21—C26—H26B 109.6
O12—C12′—H12C 109.5 C25—C26—H26B 109.6
H12A—C12′—H12C 109.5 H26A—C26—H26B 108.1
C11—C1—C2—C3 −132.89 (15) C13—C14—C15—C19 −178.12 (11)
C1—C2—C3—C31 −0.1 (2) C17—C14—C15—C19 −0.85 (13)
C1—C2—C3—C4 −179.06 (13) C14—C15—C16—O16 −179.09 (11)
C2—C3—C4—C5 2.4 (2) C19—C15—C16—O16 −2.2 (2)
C31—C3—C4—C5 −176.71 (14) C14—C15—C16—C11 0.58 (17)
C3—C4—C5—C6 175.88 (14) C19—C15—C16—C11 177.43 (12)
C4—C5—C6—O61 −6.1 (3) C12—C11—C16—O16 179.30 (11)
C4—C5—C6—O7 178.64 (16) C1—C11—C16—O16 2.11 (17)
O61—C6—O7—C8 −1.3 (3) C12—C11—C16—C15 −0.39 (17)
C5—C6—O7—C8 174.17 (15) C1—C11—C16—C15 −177.58 (11)
C6—O7—C8—C9 −99.3 (2) C13—C14—C17—O18 178.28 (12)
O7—C8—C9—N21 −164.46 (14) C15—C14—C17—O18 1.29 (13)
C2—C1—C11—C16 76.69 (15) C14—C17—O18—C19 −1.28 (13)
C2—C1—C11—C12 −100.41 (14) C17—O18—C19—O19 −179.62 (12)
C16—C11—C12—O12 −175.10 (10) C17—O18—C19—C15 0.80 (13)
C1—C11—C12—O12 2.03 (17) C14—C15—C19—O19 −179.48 (13)
C16—C11—C12—C13 0.30 (18) C16—C15—C19—O19 3.4 (2)
C1—C11—C12—C13 177.43 (11) C14—C15—C19—O18 0.06 (14)
C11—C12—O12—C12′ −99.90 (14) C16—C15—C19—O18 −177.11 (12)
C13—C12—O12—C12′ 84.43 (15) C8—C9—N21—C26 −65.89 (18)
O12—C12—C13—C14 175.01 (10) C8—C9—N21—C22 173.25 (14)
C11—C12—C13—C14 −0.36 (17) C26—N21—C22—C23 56.54 (17)
O12—C12—C13—C13′ −1.77 (17) C9—N21—C22—C23 179.24 (14)
C11—C12—C13—C13′ −177.14 (11) N21—C22—C23—O24 −58.58 (19)
C12—C13—C14—C15 0.54 (17) C22—C23—O24—C25 58.75 (18)
C13′—C13—C14—C15 177.35 (11) C23—O24—C25—C26 −58.96 (17)
C12—C13—C14—C17 −176.06 (12) C9—N21—C26—C25 −178.46 (13)
C13′—C13—C14—C17 0.8 (2) C22—N21—C26—C25 −56.82 (16)
C13—C14—C15—C16 −0.69 (18) O24—C25—C26—N21 59.15 (17)
C17—C14—C15—C16 176.58 (11)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
supporting information
sup-7 Acta Cryst. (2004). E60, o2223–o2224
O16—H16···O24i 0.85 (2) 2.07 (2) 2.7664 (15) 139 (2)
C17—H17B···O19ii 0.99 2.37 3.3205 (17) 162
C22—H22B···O61iii 0.99 2.54 3.497 (3) 163
