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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Jun 4;67(Pt 7):o1584. doi: 10.1107/S1600536811020642

Cyclo­benzaprinium salicylate

Hoong-Kun Fun a,*,‡, Chin Sing Yeap a,§, M S Siddegowda b, H S Yathirajan b, B Narayana c
PMCID: PMC3152117  PMID: 21836993

Abstract

In the title mol­ecular salt [systematic name: 3-(5H-di­benzo[a,d]cyclo­hepten-5-yl­idene)-N,N-dimethyl-1-propanaminium 2-hy­droxy­benzoate], C20H22N+·C7H5O3 −, the benzene rings of the cyclo­benzaprinium cation are inclined with a dihedral angle of 61.66 (7)°. An intra­molecular O—H⋯O hydrogen bond occurs within the salicylate anion, generating an S(6) ring. In the crystal, the cation and anion are linked by an N—H⋯O inter­action.

Related literature

For background to cyclo­benzaprine, see: Commissiong et al. (1981 ▶); Katz & Dube (1988 ▶); Cimolai (2009 ▶). For related structures, see: Bindya et al., (2007 ▶); Hemamalini & Fun (2010 ▶); Kolev et al. (2009 ▶); Thanigaimani et al. (2007 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).graphic file with name e-67-o1584-scheme1.jpg

Experimental

Crystal data

  • C20H22N+·C7H5O3 −

  • M r = 413.50

  • Triclinic, Inline graphic

  • a = 7.4700 (8) Å

  • b = 10.8408 (12) Å

  • c = 14.9724 (16) Å

  • α = 76.073 (2)°

  • β = 77.357 (1)°

  • γ = 72.574 (2)°

  • V = 1108.6 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 296 K

  • 0.37 × 0.21 × 0.15 mm

Data collection

  • Bruker APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.971, T max = 0.988

  • 22974 measured reflections

  • 6461 independent reflections

  • 4411 reflections with I > 2σ(I)

  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048

  • wR(F 2) = 0.134

  • S = 1.04

  • 6461 reflections

  • 280 parameters

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020642/hb5897sup1.cif

e-67-o1584-sup1.cif (23.1KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020642/hb5897Isup2.hkl

e-67-o1584-Isup2.hkl (316.2KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811020642/hb5897Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N1⋯O1 0.91 1.75 2.6439 (16) 167
O3—H1O3⋯O2 0.99 1.55 2.4890 (19) 157
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Acknowledgments

H-KF and CSY thank Universiti Sains Malaysia for the Research University Grant 1001/PFIZIK/811160. MSS thanks UOM for research facilities.

supplementary crystallographic information

Comment

Cyclobenzaprine is a muscle relaxant medication used to relieve skeletal muscle spasms and associated pain in acute musculoskeletal conditions. It is the most well studied drug for this application and it also has been used off-label for fibromyalgia treatment. Cyclobenzaprine has been considered structurally related to the first-generation tricyclic antidepressants (Commissiong et al., 1981; Katz & Dube, 1988; Cimolai, 2009). The crystal structures of amitriptylinium picrate (Bindya et al., 2007), benzamidinium salicylate (Kolev et al., 2009), 2-amino-5-chloropyridinium salicylate (Hemamalini & Fun, 2010) and 2-amino-4,6-dimethoxypyrimidinium salicylate (Thanigaimani et al., 2007) have been reported. We now report the crystal structure of the title compound, C20H22N+.C7H5O3-.

The asymmetric unit of the title compound consists of one cyclobenzaprinium cation and one salicylate anion (Fig. 1). The hydrogen atom of the carboxylic acid COOH group is deprotonated to the N1 atom. The two fused benzene rings of the cation make a dihedral angle of 61.66 (7)° whereas the salicylate anion is almost planar with maximum deviation of 0.063 (1) Å for atom O1. The aminium atom adopts a pyramidal conformation. The cation and anion are interconnected by N1—H1N1···O1 interaction (Table 1). An intramolecular O3—H1O3···O2 hydrogen bond (Table 1) stabilize the molecular structure of the anion molecule generating S(6) ring motif (Bernstein et al., 1995).

Experimental

Cyclobenzaprine (10 g, 0.04 mol) and salicylic acid (5.6 g, 0.04 mol) were dissolved in 50 ml of dichloromethane taken in a 100 ml round bottomed flask. Dichloromethane was distilled off under vacuum and 50 ml of ethyl acetate was added and then the flask was cooled to 278–283 K. The product formed was filtered and re-crystallized from dichloromethane to yield colourless blocks of (I) (M.p.: 415–416 K).

Refinement

The O-bound and N-bound hydrogen atoms were located from difference Fourier map and refined as riding on their parent atom, with Uiso(H) = 1.2 or 1.5 Ueq(N or O). The rest of the hydrogen atoms were positioned geomatrically [C–H = 0.93–0.97 Å] and refined using a riding model, with Uiso(H) = 1.2 or 1.5 Ueq(C).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of the title compound, with 30% probability ellipsoids for non-H atoms. Hydrogen bonds (dashed lines) are shown.

Crystal data

C20H22N+·C7H5O3− Z = 2
Mr = 413.50 F(000) = 440
Triclinic, P1 Dx = 1.239 Mg m−3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 7.4700 (8) Å Cell parameters from 5425 reflections
b = 10.8408 (12) Å θ = 2.2–29.5°
c = 14.9724 (16) Å µ = 0.08 mm−1
α = 76.073 (2)° T = 296 K
β = 77.357 (1)° Block, colourless
γ = 72.574 (2)° 0.37 × 0.21 × 0.15 mm
V = 1108.6 (2) Å3
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Data collection

Bruker APEXII DUO CCD diffractometer 6461 independent reflections
Radiation source: fine-focus sealed tube 4411 reflections with I > 2σ(I)
graphite Rint = 0.028
φ and ω scans θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009) h = −10→10
Tmin = 0.971, Tmax = 0.988 k = −15→15
22974 measured reflections l = −21→21
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134 H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0573P)2 + 0.147P] where P = (Fo2 + 2Fc2)/3
6461 reflections (Δ/σ)max < 0.001
280 parameters Δρmax = 0.21 e Å−3
0 restraints Δρmin = −0.18 e Å−3
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
N1 −0.33126 (15) 0.09099 (10) 0.18470 (7) 0.0423 (2)
H1N1 −0.2275 0.0547 0.2133 0.051*
C1 0.05014 (15) 0.33798 (12) 0.18708 (8) 0.0361 (3)
C2 0.10142 (17) 0.26220 (14) 0.11781 (9) 0.0431 (3)
H2A 0.0675 0.1833 0.1295 0.052*
C3 0.2020 (2) 0.30282 (17) 0.03200 (10) 0.0564 (4)
H3A 0.2353 0.2513 −0.0136 0.068*
C4 0.2527 (2) 0.41904 (18) 0.01409 (11) 0.0640 (4)
H4A 0.3199 0.4464 −0.0437 0.077*
C5 0.2045 (2) 0.49480 (15) 0.08118 (12) 0.0590 (4)
H5A 0.2374 0.5743 0.0677 0.071*
C6 0.10616 (17) 0.45507 (12) 0.17007 (10) 0.0438 (3)
C7 0.0743 (2) 0.53280 (14) 0.24161 (12) 0.0537 (4)
H7A 0.0442 0.6237 0.2222 0.064*
C8 0.0834 (2) 0.48787 (15) 0.33202 (12) 0.0557 (4)
H8A 0.0614 0.5510 0.3684 0.067*
C9 0.12425 (18) 0.35065 (14) 0.38045 (9) 0.0457 (3)
C10 0.2302 (2) 0.31229 (19) 0.45369 (11) 0.0607 (4)
H10A 0.2667 0.3758 0.4723 0.073*
C11 0.2813 (2) 0.1843 (2) 0.49850 (11) 0.0669 (5)
H11A 0.3535 0.1613 0.5462 0.080*
C12 0.2254 (2) 0.08934 (17) 0.47281 (10) 0.0594 (4)
H12A 0.2608 0.0020 0.5028 0.071*
C13 0.11665 (18) 0.12385 (14) 0.40225 (9) 0.0457 (3)
H13A 0.0782 0.0596 0.3857 0.055*
C14 0.06458 (16) 0.25355 (13) 0.35607 (8) 0.0376 (3)
C15 −0.05187 (16) 0.28950 (11) 0.28004 (8) 0.0347 (2)
C16 −0.22561 (17) 0.27224 (12) 0.29535 (9) 0.0392 (3)
H16A −0.2678 0.2322 0.3553 0.047*
C17 −0.36111 (17) 0.30986 (13) 0.22713 (10) 0.0436 (3)
H17A −0.2928 0.3319 0.1650 0.052*
H17B −0.4586 0.3884 0.2404 0.052*
C18 −0.45677 (17) 0.20412 (13) 0.22789 (10) 0.0434 (3)
H18A −0.5051 0.1707 0.2919 0.052*
H18B −0.5648 0.2441 0.1951 0.052*
C19 −0.2757 (2) 0.12856 (18) 0.08299 (10) 0.0621 (4)
H19A −0.1936 0.0531 0.0588 0.093*
H19B −0.2101 0.1962 0.0704 0.093*
H19C −0.3874 0.1608 0.0537 0.093*
C20 −0.4273 (3) −0.01685 (17) 0.20561 (14) 0.0736 (5)
H20A −0.3458 −0.0895 0.1780 0.110*
H20B −0.5440 0.0143 0.1805 0.110*
H20C −0.4540 −0.0450 0.2719 0.110*
O1 −0.05304 (14) −0.04235 (10) 0.28085 (7) 0.0564 (3)
O2 0.10069 (17) −0.09085 (12) 0.14508 (7) 0.0724 (4)
O3 0.42092 (17) −0.24876 (12) 0.13184 (7) 0.0674 (3)
H1O3 0.2980 −0.1850 0.1204 0.101*
C21 0.22965 (19) −0.23076 (12) 0.37511 (9) 0.0433 (3)
H21A 0.1221 −0.1879 0.4115 0.052*
C22 0.3758 (2) −0.32023 (15) 0.41757 (11) 0.0570 (4)
H22A 0.3665 −0.3378 0.4821 0.068*
C23 0.5356 (2) −0.38335 (15) 0.36347 (12) 0.0601 (4)
H23A 0.6346 −0.4429 0.3919 0.072*
C24 0.5504 (2) −0.35955 (14) 0.26882 (11) 0.0540 (4)
H24A 0.6591 −0.4028 0.2332 0.065*
C25 0.40337 (18) −0.27075 (13) 0.22540 (9) 0.0429 (3)
C26 0.24146 (16) −0.20414 (11) 0.27883 (8) 0.0356 (2)
C27 0.08451 (18) −0.10603 (12) 0.23224 (9) 0.0420 (3)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
N1 0.0371 (5) 0.0432 (6) 0.0491 (6) −0.0090 (4) −0.0163 (4) −0.0070 (5)
C1 0.0256 (5) 0.0387 (6) 0.0429 (6) −0.0071 (4) −0.0102 (4) −0.0030 (5)
C2 0.0332 (6) 0.0510 (7) 0.0451 (7) −0.0094 (5) −0.0098 (5) −0.0078 (6)
C3 0.0451 (8) 0.0727 (10) 0.0442 (7) −0.0068 (7) −0.0065 (6) −0.0088 (7)
C4 0.0516 (9) 0.0745 (11) 0.0502 (9) −0.0140 (8) −0.0029 (7) 0.0098 (8)
C5 0.0463 (8) 0.0496 (8) 0.0722 (10) −0.0172 (7) −0.0128 (7) 0.0142 (7)
C6 0.0316 (6) 0.0389 (6) 0.0579 (8) −0.0086 (5) −0.0121 (5) 0.0002 (5)
C7 0.0446 (7) 0.0371 (7) 0.0827 (11) −0.0119 (6) −0.0166 (7) −0.0098 (7)
C8 0.0485 (8) 0.0519 (8) 0.0783 (11) −0.0163 (6) −0.0111 (7) −0.0290 (7)
C9 0.0358 (6) 0.0596 (8) 0.0490 (7) −0.0170 (6) −0.0041 (5) −0.0208 (6)
C10 0.0550 (9) 0.0886 (12) 0.0540 (9) −0.0301 (8) −0.0129 (7) −0.0239 (8)
C11 0.0573 (9) 0.1065 (14) 0.0440 (8) −0.0310 (9) −0.0176 (7) −0.0063 (8)
C12 0.0522 (8) 0.0754 (10) 0.0450 (8) −0.0196 (8) −0.0119 (6) 0.0066 (7)
C13 0.0402 (7) 0.0547 (8) 0.0419 (7) −0.0172 (6) −0.0048 (5) −0.0039 (6)
C14 0.0284 (5) 0.0493 (7) 0.0371 (6) −0.0126 (5) −0.0017 (4) −0.0119 (5)
C15 0.0297 (5) 0.0345 (6) 0.0422 (6) −0.0094 (4) −0.0059 (4) −0.0101 (5)
C16 0.0330 (6) 0.0407 (6) 0.0452 (7) −0.0120 (5) −0.0054 (5) −0.0081 (5)
C17 0.0306 (6) 0.0403 (6) 0.0607 (8) −0.0071 (5) −0.0134 (5) −0.0080 (6)
C18 0.0264 (5) 0.0502 (7) 0.0557 (7) −0.0107 (5) −0.0092 (5) −0.0105 (6)
C19 0.0550 (9) 0.0819 (11) 0.0481 (8) −0.0085 (8) −0.0176 (7) −0.0131 (7)
C20 0.0793 (12) 0.0570 (10) 0.1005 (14) −0.0321 (9) −0.0296 (10) −0.0127 (9)
O1 0.0484 (6) 0.0553 (6) 0.0579 (6) 0.0085 (5) −0.0183 (5) −0.0156 (5)
O2 0.0730 (8) 0.0825 (8) 0.0445 (6) 0.0097 (6) −0.0213 (5) −0.0066 (5)
O3 0.0636 (7) 0.0813 (8) 0.0473 (6) −0.0044 (6) 0.0015 (5) −0.0210 (5)
C21 0.0460 (7) 0.0404 (7) 0.0433 (7) −0.0075 (5) −0.0102 (5) −0.0093 (5)
C22 0.0682 (10) 0.0537 (8) 0.0500 (8) −0.0087 (7) −0.0267 (7) −0.0049 (6)
C23 0.0536 (9) 0.0471 (8) 0.0803 (11) 0.0029 (7) −0.0348 (8) −0.0120 (7)
C24 0.0399 (7) 0.0470 (8) 0.0751 (10) −0.0003 (6) −0.0117 (7) −0.0229 (7)
C25 0.0418 (7) 0.0405 (7) 0.0488 (7) −0.0107 (5) −0.0066 (5) −0.0133 (5)
C26 0.0357 (6) 0.0306 (5) 0.0424 (6) −0.0084 (4) −0.0108 (5) −0.0069 (5)
C27 0.0438 (7) 0.0370 (6) 0.0460 (7) −0.0069 (5) −0.0159 (5) −0.0059 (5)
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Geometric parameters (Å, °)

N1—C19 1.4775 (18) C14—C15 1.4904 (16)
N1—C20 1.4855 (19) C15—C16 1.3291 (16)
N1—C18 1.4930 (17) C16—C17 1.4963 (17)
N1—H1N1 0.9057 C16—H16A 0.9300
C1—C2 1.3947 (18) C17—C18 1.5184 (18)
C1—C6 1.4026 (17) C17—H17A 0.9700
C1—C15 1.4892 (17) C17—H17B 0.9700
C2—C3 1.3828 (19) C18—H18A 0.9700
C2—H2A 0.9300 C18—H18B 0.9700
C3—C4 1.372 (2) C19—H19A 0.9600
C3—H3A 0.9300 C19—H19B 0.9600
C4—C5 1.369 (2) C19—H19C 0.9600
C4—H4A 0.9300 C20—H20A 0.9600
C5—C6 1.408 (2) C20—H20B 0.9600
C5—H5A 0.9300 C20—H20C 0.9600
C6—C7 1.455 (2) O1—C27 1.2457 (16)
C7—C8 1.333 (2) O2—C27 1.2586 (16)
C7—H7A 0.9300 O3—C25 1.3468 (16)
C8—C9 1.462 (2) O3—H1O3 0.9910
C8—H8A 0.9300 C21—C22 1.3819 (18)
C9—C10 1.4017 (19) C21—C26 1.3888 (17)
C9—C14 1.4061 (18) C21—H21A 0.9300
C10—C11 1.367 (3) C22—C23 1.380 (2)
C10—H10A 0.9300 C22—H22A 0.9300
C11—C12 1.378 (2) C23—C24 1.364 (2)
C11—H11A 0.9300 C23—H23A 0.9300
C12—C13 1.3855 (19) C24—C25 1.3907 (19)
C12—H12A 0.9300 C24—H24A 0.9300
C13—C14 1.3887 (19) C25—C26 1.3984 (17)
C13—H13A 0.9300 C26—C27 1.4988 (16)
C19—N1—C20 110.16 (12) C1—C15—C14 113.33 (9)
C19—N1—C18 112.70 (11) C15—C16—C17 127.45 (12)
C20—N1—C18 109.75 (12) C15—C16—H16A 116.3
C19—N1—H1N1 110.9 C17—C16—H16A 116.3
C20—N1—H1N1 103.5 C16—C17—C18 114.56 (11)
C18—N1—H1N1 109.5 C16—C17—H17A 108.6
C2—C1—C6 119.35 (12) C18—C17—H17A 108.6
C2—C1—C15 119.75 (11) C16—C17—H17B 108.6
C6—C1—C15 120.77 (11) C18—C17—H17B 108.6
C3—C2—C1 120.88 (14) H17A—C17—H17B 107.6
C3—C2—H2A 119.6 N1—C18—C17 114.71 (10)
C1—C2—H2A 119.6 N1—C18—H18A 108.6
C4—C3—C2 120.01 (15) C17—C18—H18A 108.6
C4—C3—H3A 120.0 N1—C18—H18B 108.6
C2—C3—H3A 120.0 C17—C18—H18B 108.6
C5—C4—C3 120.11 (14) H18A—C18—H18B 107.6
C5—C4—H4A 119.9 N1—C19—H19A 109.5
C3—C4—H4A 119.9 N1—C19—H19B 109.5
C4—C5—C6 121.47 (15) H19A—C19—H19B 109.5
C4—C5—H5A 119.3 N1—C19—H19C 109.5
C6—C5—H5A 119.3 H19A—C19—H19C 109.5
C1—C6—C5 118.11 (13) H19B—C19—H19C 109.5
C1—C6—C7 122.59 (12) N1—C20—H20A 109.5
C5—C6—C7 119.24 (13) N1—C20—H20B 109.5
C8—C7—C6 127.09 (13) H20A—C20—H20B 109.5
C8—C7—H7A 116.5 N1—C20—H20C 109.5
C6—C7—H7A 116.5 H20A—C20—H20C 109.5
C7—C8—C9 127.38 (13) H20B—C20—H20C 109.5
C7—C8—H8A 116.3 C25—O3—H1O3 102.1
C9—C8—H8A 116.3 C22—C21—C26 120.81 (13)
C10—C9—C14 117.85 (14) C22—C21—H21A 119.6
C10—C9—C8 119.14 (13) C26—C21—H21A 119.6
C14—C9—C8 123.00 (12) C23—C22—C21 119.49 (14)
C11—C10—C9 121.92 (15) C23—C22—H22A 120.3
C11—C10—H10A 119.0 C21—C22—H22A 120.3
C9—C10—H10A 119.0 C24—C23—C22 120.90 (13)
C10—C11—C12 119.78 (14) C24—C23—H23A 119.5
C10—C11—H11A 120.1 C22—C23—H23A 119.5
C12—C11—H11A 120.1 C23—C24—C25 120.11 (13)
C11—C12—C13 120.04 (15) C23—C24—H24A 119.9
C11—C12—H12A 120.0 C25—C24—H24A 119.9
C13—C12—H12A 120.0 O3—C25—C24 119.13 (12)
C12—C13—C14 120.62 (14) O3—C25—C26 120.96 (12)
C12—C13—H13A 119.7 C24—C25—C26 119.91 (12)
C14—C13—H13A 119.7 C21—C26—C25 118.77 (11)
C13—C14—C9 119.76 (12) C21—C26—C27 121.09 (11)
C13—C14—C15 120.17 (11) C25—C26—C27 120.13 (11)
C9—C14—C15 120.06 (11) O1—C27—O2 123.33 (12)
C16—C15—C1 124.75 (11) O1—C27—C26 118.89 (11)
C16—C15—C14 121.83 (11) O2—C27—C26 117.77 (12)
C6—C1—C2—C3 −1.77 (17) C6—C1—C15—C16 118.97 (14)
C15—C1—C2—C3 −177.74 (11) C2—C1—C15—C14 111.50 (12)
C1—C2—C3—C4 0.0 (2) C6—C1—C15—C14 −64.41 (14)
C2—C3—C4—C5 0.2 (2) C13—C14—C15—C16 61.58 (16)
C3—C4—C5—C6 1.3 (2) C9—C14—C15—C16 −119.26 (14)
C2—C1—C6—C5 3.19 (17) C13—C14—C15—C1 −115.15 (12)
C15—C1—C6—C5 179.12 (11) C9—C14—C15—C1 64.01 (14)
C2—C1—C6—C7 −173.92 (11) C1—C15—C16—C17 −7.0 (2)
C15—C1—C6—C7 2.01 (17) C14—C15—C16—C17 176.69 (11)
C4—C5—C6—C1 −3.0 (2) C15—C16—C17—C18 134.27 (14)
C4—C5—C6—C7 174.19 (13) C19—N1—C18—C17 −67.76 (14)
C1—C6—C7—C8 36.3 (2) C20—N1—C18—C17 169.07 (12)
C5—C6—C7—C8 −140.80 (16) C16—C17—C18—N1 −73.67 (15)
C6—C7—C8—C9 −1.2 (2) C26—C21—C22—C23 0.3 (2)
C7—C8—C9—C10 144.17 (16) C21—C22—C23—C24 −0.6 (2)
C7—C8—C9—C14 −34.8 (2) C22—C23—C24—C25 0.0 (2)
C14—C9—C10—C11 2.4 (2) C23—C24—C25—O3 −179.97 (14)
C8—C9—C10—C11 −176.58 (15) C23—C24—C25—C26 1.1 (2)
C9—C10—C11—C12 −1.1 (3) C22—C21—C26—C25 0.73 (19)
C10—C11—C12—C13 −0.5 (2) C22—C21—C26—C27 −179.26 (13)
C11—C12—C13—C14 0.7 (2) O3—C25—C26—C21 179.66 (12)
C12—C13—C14—C9 0.62 (19) C24—C25—C26—C21 −1.40 (19)
C12—C13—C14—C15 179.78 (12) O3—C25—C26—C27 −0.35 (19)
C10—C9—C14—C13 −2.13 (18) C24—C25—C26—C27 178.59 (12)
C8—C9—C14—C13 176.83 (12) C21—C26—C27—O1 4.18 (19)
C10—C9—C14—C15 178.71 (12) C25—C26—C27—O1 −175.80 (12)
C8—C9—C14—C15 −2.33 (19) C21—C26—C27—O2 −176.97 (13)
C2—C1—C15—C16 −65.12 (16) C25—C26—C27—O2 3.04 (19)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
N1—H1N1···O1 0.91 1.75 2.6439 (16) 167
O3—H1O3···O2 0.99 1.55 2.4890 (19) 157
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5897).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020642/hb5897sup1.cif

e-67-o1584-sup1.cif (23.1KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020642/hb5897Isup2.hkl

e-67-o1584-Isup2.hkl (316.2KB, hkl)

Supplementary material file. DOI: 10.1107/S1600536811020642/hb5897Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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