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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1067.
Published online 2009 April 18. doi:  10.1107/S1600536809013786
PMCID: PMC2977747

5-Meth­oxy-2-[(2-morpholinoeth­yl)­iminio­meth­yl]phenolate

Abstract

Each of the two independent mol­ecules of the title comound, C14H20N2O3, exists in the zwitterionic form as the imino N atoms are protonated. The =N—H unit forms an intra­molecular hydrogen bond to the negatively charged O atom, and also a weaker intermolecular N—H(...)O bond, the latter resulting in inversion dimers.

Related literature

For the structure of 2-[(2-morpholinoethyl­imino)­methyl]­phenol, see: Petek et al. (2005 [triangle]).

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Object name is e-65-o1067-scheme1.jpg

Experimental

Crystal data

  • C14H20N2O3
  • M r = 264.32
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1067-efi1.jpg
  • a = 10.4022 (2) Å
  • b = 10.7340 (2) Å
  • c = 14.3497 (3) Å
  • α = 83.523 (1)°
  • β = 74.810 (1)°
  • γ = 60.768 (1)°
  • V = 1349.13 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.25 × 0.25 × 0.25 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 9402 measured reflections
  • 5948 independent reflections
  • 4990 reflections with I > 2σ(I)
  • R int = 0.019

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.122
  • S = 1.04
  • 5948 reflections
  • 353 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013786/tk2422sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013786/tk2422Isup2.hkl

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

Acknowledgments

The authors thank the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

2-Hydroxy-4-methoxybenzaldehyde (0.3 g, 2 mmol) and N-(2-aminoethyl)morpholine (0.26 g, 2 mmol) were heated in acidified ethanol (50 ml) for 8 h. The solvent was removed to give an oil; crystals appeared in the oil after several days.

Refinement

H atoms were placed at calculated positions (C—H = 0.95–0.99 Å) and were treated as riding on their parent C atoms, with U(H) set to 1.2–1.5 times Ueq(C). The iminium H atoms were located in a difference Fourier map, and were refined with a distance restraint of N—H = 0.88 (1) Å; their temperature factors were refined.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C14H20N2O3 at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.

Crystal data

C14H20N2O3Z = 4
Mr = 264.32F(000) = 568
Triclinic, P1Dx = 1.301 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.4022 (2) ÅCell parameters from 4712 reflections
b = 10.7340 (2) Åθ = 2.3–28.3°
c = 14.3497 (3) ŵ = 0.09 mm1
α = 83.523 (1)°T = 100 K
β = 74.810 (1)°Block, yellow
γ = 60.768 (1)°0.25 × 0.25 × 0.25 mm
V = 1349.13 (5) Å3

Data collection

Bruker SMART APEX diffractometer4990 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.019
graphiteθmax = 27.5°, θmin = 1.5°
ω scansh = −13→13
9402 measured reflectionsk = −13→13
5948 independent reflectionsl = −18→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0696P)2 + 0.3249P] where P = (Fo2 + 2Fc2)/3
5948 reflections(Δ/σ)max = 0.001
353 parametersΔρmax = 0.31 e Å3
2 restraintsΔρmin = −0.28 e Å3

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

xyzUiso*/Ueq
O10.98316 (10)0.43387 (9)0.41326 (7)0.0206 (2)
O20.96310 (10)0.15768 (9)0.18272 (6)0.0212 (2)
O30.38917 (12)0.92759 (12)0.95202 (8)0.0352 (3)
O41.50070 (10)−0.11554 (10)−0.55972 (7)0.0248 (2)
O51.47841 (10)−0.36606 (9)−0.80663 (6)0.0207 (2)
O60.93660 (11)0.37780 (10)−0.02785 (6)0.0226 (2)
N10.77639 (12)0.49804 (11)0.57933 (8)0.0179 (2)
H10.8542 (15)0.5066 (19)0.5426 (11)0.039 (5)*
N20.60959 (11)0.75546 (11)0.78788 (7)0.0168 (2)
N31.23596 (12)0.09777 (11)−0.46514 (8)0.0201 (2)
H31.3361 (10)0.0512 (16)−0.4734 (12)0.034 (5)*
N41.02064 (11)0.24956 (10)−0.21452 (7)0.0163 (2)
C10.91918 (13)0.37426 (12)0.38550 (9)0.0157 (2)
C20.98177 (13)0.29765 (12)0.29480 (9)0.0165 (2)
H21.07320.29090.25400.020*
C30.91073 (14)0.23419 (12)0.26664 (9)0.0165 (2)
C40.77322 (14)0.24178 (12)0.32475 (9)0.0178 (3)
H40.72490.19880.30320.021*
C50.71188 (13)0.31159 (12)0.41178 (9)0.0174 (2)
H50.62080.31580.45120.021*
C60.78113 (13)0.37826 (12)0.44499 (9)0.0157 (2)
C71.11022 (15)0.12990 (14)0.12544 (9)0.0226 (3)
H7A1.13820.06870.06990.034*
H7B1.18500.08170.16470.034*
H7C1.10800.22030.10260.034*
C80.72030 (14)0.43854 (12)0.53895 (9)0.0171 (2)
H80.63150.43570.57590.021*
C90.72088 (15)0.54438 (13)0.68036 (9)0.0193 (3)
H9A0.80660.50110.71220.023*
H9B0.64700.51150.71390.023*
C100.64529 (14)0.70646 (13)0.68841 (9)0.0180 (3)
H10A0.71360.74010.64600.022*
H10B0.55060.74890.66570.022*
C110.54085 (16)0.91155 (14)0.78853 (10)0.0248 (3)
H11A0.45220.95240.75950.030*
H11B0.61540.93990.74860.030*
C120.49055 (17)0.97165 (15)0.88980 (10)0.0297 (3)
H12A0.58070.93940.91610.036*
H12B0.43971.07720.88770.036*
C130.46395 (18)0.77580 (18)0.95435 (10)0.0333 (4)
H13A0.39650.74390.99980.040*
H13B0.55680.74150.97800.040*
C140.50611 (16)0.71168 (16)0.85489 (10)0.0271 (3)
H14A0.55580.60620.85840.032*
H14B0.41340.74460.83130.032*
C151.42646 (14)−0.13723 (13)−0.60736 (9)0.0178 (3)
C161.49985 (14)−0.24612 (12)−0.68219 (9)0.0176 (3)
H161.6069−0.3044−0.69590.021*
C171.41790 (14)−0.26689 (12)−0.73376 (9)0.0168 (2)
C181.25664 (14)−0.18526 (13)−0.71453 (9)0.0187 (3)
H181.2014−0.2031−0.74970.022*
C191.18346 (14)−0.08089 (13)−0.64448 (9)0.0184 (3)
H191.0762−0.0254−0.63180.022*
C201.26264 (14)−0.05270 (12)−0.59010 (9)0.0172 (2)
C211.64017 (15)−0.44652 (14)−0.83657 (10)0.0248 (3)
H21A1.6685−0.5143−0.88810.037*
H21B1.6807−0.4988−0.78150.037*
H21C1.6821−0.3815−0.86060.037*
C221.17933 (14)0.05782 (13)−0.51997 (9)0.0185 (3)
H221.07230.1080−0.51160.022*
C231.14126 (15)0.21047 (13)−0.39115 (9)0.0216 (3)
H23A1.03900.2691−0.40370.026*
H23B1.18660.2735−0.39350.026*
C241.12827 (14)0.14453 (12)−0.29159 (9)0.0181 (3)
H24A1.09590.0721−0.29280.022*
H24B1.22950.0951−0.27690.022*
C251.07626 (14)0.34487 (13)−0.19663 (9)0.0192 (3)
H25A1.09050.3981−0.25600.023*
H25B1.17580.2874−0.18020.023*
C260.96492 (15)0.44957 (13)−0.11458 (9)0.0208 (3)
H26A1.00610.5105−0.10250.025*
H26B0.86820.5123−0.13350.025*
C270.88279 (15)0.28513 (14)−0.04521 (9)0.0222 (3)
H27A0.78510.3425−0.06400.027*
H27B0.86470.23500.01500.027*
C280.99553 (15)0.17629 (13)−0.12430 (9)0.0197 (3)
H28A1.09280.1171−0.10520.024*
H28B0.95620.1126−0.13410.024*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0209 (5)0.0253 (5)0.0202 (5)−0.0151 (4)−0.0019 (4)−0.0037 (4)
O20.0215 (5)0.0235 (4)0.0180 (5)−0.0106 (4)−0.0018 (4)−0.0062 (4)
O30.0228 (5)0.0519 (7)0.0277 (6)−0.0175 (5)0.0070 (4)−0.0198 (5)
O40.0196 (5)0.0286 (5)0.0258 (5)−0.0094 (4)−0.0061 (4)−0.0070 (4)
O50.0196 (5)0.0214 (4)0.0209 (5)−0.0100 (4)−0.0010 (4)−0.0069 (4)
O60.0290 (5)0.0254 (5)0.0166 (5)−0.0158 (4)−0.0034 (4)−0.0028 (4)
N10.0177 (5)0.0197 (5)0.0152 (5)−0.0093 (4)−0.0004 (4)−0.0020 (4)
N20.0167 (5)0.0195 (5)0.0132 (5)−0.0089 (4)−0.0008 (4)−0.0013 (4)
N30.0181 (5)0.0199 (5)0.0174 (5)−0.0061 (4)−0.0012 (4)−0.0033 (4)
N40.0173 (5)0.0173 (5)0.0141 (5)−0.0087 (4)−0.0014 (4)−0.0028 (4)
C10.0158 (6)0.0148 (5)0.0162 (6)−0.0071 (4)−0.0045 (5)0.0014 (4)
C20.0153 (6)0.0170 (5)0.0158 (6)−0.0074 (5)−0.0022 (5)0.0007 (4)
C30.0174 (6)0.0140 (5)0.0151 (6)−0.0047 (4)−0.0048 (5)−0.0003 (4)
C40.0172 (6)0.0178 (5)0.0216 (6)−0.0095 (5)−0.0074 (5)0.0008 (5)
C50.0142 (5)0.0172 (5)0.0194 (6)−0.0072 (5)−0.0037 (5)0.0027 (5)
C60.0144 (5)0.0149 (5)0.0160 (6)−0.0060 (4)−0.0031 (4)0.0008 (4)
C70.0221 (6)0.0224 (6)0.0182 (6)−0.0087 (5)0.0009 (5)−0.0033 (5)
C80.0146 (6)0.0164 (5)0.0180 (6)−0.0066 (5)−0.0022 (5)0.0011 (4)
C90.0224 (6)0.0213 (6)0.0139 (6)−0.0115 (5)−0.0012 (5)−0.0015 (5)
C100.0171 (6)0.0209 (6)0.0139 (6)−0.0079 (5)−0.0021 (5)−0.0015 (5)
C110.0258 (7)0.0208 (6)0.0200 (7)−0.0048 (5)−0.0047 (5)−0.0034 (5)
C120.0300 (7)0.0288 (7)0.0245 (7)−0.0109 (6)0.0001 (6)−0.0090 (6)
C130.0389 (8)0.0540 (9)0.0177 (7)−0.0346 (8)0.0055 (6)−0.0074 (6)
C140.0290 (7)0.0415 (8)0.0183 (7)−0.0251 (7)0.0019 (5)−0.0056 (6)
C150.0190 (6)0.0188 (5)0.0159 (6)−0.0099 (5)−0.0034 (5)0.0011 (4)
C160.0146 (6)0.0178 (5)0.0189 (6)−0.0073 (5)−0.0021 (5)−0.0004 (5)
C170.0199 (6)0.0151 (5)0.0150 (6)−0.0093 (5)−0.0014 (5)0.0001 (4)
C180.0187 (6)0.0213 (6)0.0191 (6)−0.0110 (5)−0.0063 (5)0.0013 (5)
C190.0158 (6)0.0184 (6)0.0187 (6)−0.0071 (5)−0.0037 (5)0.0029 (5)
C200.0176 (6)0.0170 (5)0.0152 (6)−0.0078 (5)−0.0026 (5)0.0013 (4)
C210.0208 (6)0.0220 (6)0.0275 (7)−0.0086 (5)0.0008 (5)−0.0084 (5)
C220.0176 (6)0.0188 (6)0.0170 (6)−0.0080 (5)−0.0031 (5)0.0026 (5)
C230.0216 (6)0.0195 (6)0.0188 (6)−0.0061 (5)−0.0023 (5)−0.0051 (5)
C240.0168 (6)0.0170 (5)0.0183 (6)−0.0055 (5)−0.0044 (5)−0.0038 (5)
C250.0199 (6)0.0207 (6)0.0185 (6)−0.0115 (5)−0.0021 (5)−0.0024 (5)
C260.0253 (7)0.0204 (6)0.0187 (6)−0.0127 (5)−0.0035 (5)−0.0028 (5)
C270.0242 (7)0.0271 (6)0.0183 (6)−0.0158 (6)−0.0016 (5)−0.0017 (5)
C280.0237 (6)0.0206 (6)0.0178 (6)−0.0128 (5)−0.0048 (5)0.0000 (5)

Geometric parameters (Å, °)

O1—C11.2741 (15)C10—H10B0.9900
O2—C31.3652 (14)C11—C121.5115 (18)
O2—C71.4342 (15)C11—H11A0.9900
O3—C131.423 (2)C11—H11B0.9900
O3—C121.4253 (18)C12—H12A0.9900
O4—C151.2673 (16)C12—H12B0.9900
O5—C171.3691 (14)C13—C141.5172 (18)
O5—C211.4308 (15)C13—H13A0.9900
O6—C271.4274 (15)C13—H13B0.9900
O6—C261.4291 (15)C14—H14A0.9900
N1—C81.3071 (16)C14—H14B0.9900
N1—C91.4581 (16)C15—C161.4436 (17)
N1—H10.883 (9)C15—C201.4518 (17)
N2—C111.4657 (16)C16—C171.3702 (18)
N2—C101.4673 (15)C16—H160.9500
N2—C141.4676 (16)C17—C181.4263 (17)
N3—C221.3097 (17)C18—C191.3657 (17)
N3—C231.4625 (15)C18—H180.9500
N3—H30.889 (9)C19—C201.4187 (18)
N4—C241.4654 (15)C19—H190.9500
N4—C281.4685 (16)C20—C221.4068 (17)
N4—C251.4706 (15)C21—H21A0.9800
C1—C21.4383 (16)C21—H21B0.9800
C1—C61.4486 (16)C21—H21C0.9800
C2—C31.3724 (17)C22—H220.9500
C2—H20.9500C23—C241.5246 (18)
C3—C41.4229 (17)C23—H23A0.9900
C4—C51.3619 (17)C23—H23B0.9900
C4—H40.9500C24—H24A0.9900
C5—C61.4207 (17)C24—H24B0.9900
C5—H50.9500C25—C261.5177 (17)
C6—C81.4096 (17)C25—H25A0.9900
C7—H7A0.9800C25—H25B0.9900
C7—H7B0.9800C26—H26A0.9900
C7—H7C0.9800C26—H26B0.9900
C8—H80.9500C27—C281.5138 (17)
C9—C101.5231 (16)C27—H27A0.9900
C9—H9A0.9900C27—H27B0.9900
C9—H9B0.9900C28—H28A0.9900
C10—H10A0.9900C28—H28B0.9900
C3—O2—C7117.10 (10)C14—C13—H13B109.4
C13—O3—C12108.59 (10)H13A—C13—H13B108.0
C17—O5—C21117.66 (10)N2—C14—C13109.57 (11)
C27—O6—C26109.87 (9)N2—C14—H14A109.8
C8—N1—C9123.55 (11)C13—C14—H14A109.8
C8—N1—H1116.5 (12)N2—C14—H14B109.8
C9—N1—H1119.9 (12)C13—C14—H14B109.8
C11—N2—C10108.28 (10)H14A—C14—H14B108.2
C11—N2—C14109.75 (10)O4—C15—C16122.00 (11)
C10—N2—C14112.35 (10)O4—C15—C20121.65 (11)
C22—N3—C23122.71 (11)C16—C15—C20116.34 (11)
C22—N3—H3116.9 (11)C17—C16—C15121.19 (11)
C23—N3—H3120.4 (11)C17—C16—H16119.4
C24—N4—C28109.97 (9)C15—C16—H16119.4
C24—N4—C25111.83 (9)O5—C17—C16124.99 (11)
C28—N4—C25108.10 (10)O5—C17—C18113.13 (11)
O1—C1—C2121.77 (11)C16—C17—C18121.87 (11)
O1—C1—C6121.36 (11)C19—C18—C17118.51 (11)
C2—C1—C6116.85 (11)C19—C18—H18120.7
C3—C2—C1120.63 (11)C17—C18—H18120.7
C3—C2—H2119.7C18—C19—C20122.08 (11)
C1—C2—H2119.7C18—C19—H19119.0
O2—C3—C2124.61 (11)C20—C19—H19119.0
O2—C3—C4113.45 (10)C22—C20—C19118.70 (11)
C2—C3—C4121.95 (11)C22—C20—C15121.32 (11)
C5—C4—C3119.04 (11)C19—C20—C15119.98 (11)
C5—C4—H4120.5O5—C21—H21A109.5
C3—C4—H4120.5O5—C21—H21B109.5
C4—C5—C6121.45 (11)H21A—C21—H21B109.5
C4—C5—H5119.3O5—C21—H21C109.5
C6—C5—H5119.3H21A—C21—H21C109.5
C8—C6—C5119.15 (11)H21B—C21—H21C109.5
C8—C6—C1120.63 (11)N3—C22—C20125.90 (12)
C5—C6—C1120.06 (11)N3—C22—H22117.1
O2—C7—H7A109.5C20—C22—H22117.1
O2—C7—H7B109.5N3—C23—C24109.88 (10)
H7A—C7—H7B109.5N3—C23—H23A109.7
O2—C7—H7C109.5C24—C23—H23A109.7
H7A—C7—H7C109.5N3—C23—H23B109.7
H7B—C7—H7C109.5C24—C23—H23B109.7
N1—C8—C6125.19 (11)H23A—C23—H23B108.2
N1—C8—H8117.4N4—C24—C23113.23 (10)
C6—C8—H8117.4N4—C24—H24A108.9
N1—C9—C10110.56 (10)C23—C24—H24A108.9
N1—C9—H9A109.5N4—C24—H24B108.9
C10—C9—H9A109.5C23—C24—H24B108.9
N1—C9—H9B109.5H24A—C24—H24B107.7
C10—C9—H9B109.5N4—C25—C26110.72 (10)
H9A—C9—H9B108.1N4—C25—H25A109.5
N2—C10—C9111.97 (10)C26—C25—H25A109.5
N2—C10—H10A109.2N4—C25—H25B109.5
C9—C10—H10A109.2C26—C25—H25B109.5
N2—C10—H10B109.2H25A—C25—H25B108.1
C9—C10—H10B109.2O6—C26—C25111.69 (10)
H10A—C10—H10B107.9O6—C26—H26A109.3
N2—C11—C12111.64 (11)C25—C26—H26A109.3
N2—C11—H11A109.3O6—C26—H26B109.3
C12—C11—H11A109.3C25—C26—H26B109.3
N2—C11—H11B109.3H26A—C26—H26B107.9
C12—C11—H11B109.3O6—C27—C28111.39 (10)
H11A—C11—H11B108.0O6—C27—H27A109.3
O3—C12—C11111.69 (12)C28—C27—H27A109.3
O3—C12—H12A109.3O6—C27—H27B109.3
C11—C12—H12A109.3C28—C27—H27B109.3
O3—C12—H12B109.3H27A—C27—H27B108.0
C11—C12—H12B109.3N4—C28—C27109.79 (10)
H12A—C12—H12B107.9N4—C28—H28A109.7
O3—C13—C14111.10 (13)C27—C28—H28A109.7
O3—C13—H13A109.4N4—C28—H28B109.7
C14—C13—H13A109.4C27—C28—H28B109.7
O3—C13—H13B109.4H28A—C28—H28B108.2
O1—C1—C2—C3179.90 (11)O4—C15—C16—C17−179.19 (11)
C6—C1—C2—C31.07 (16)C20—C15—C16—C170.26 (17)
C7—O2—C3—C26.74 (17)C21—O5—C17—C16−5.24 (18)
C7—O2—C3—C4−172.62 (10)C21—O5—C17—C18175.49 (10)
C1—C2—C3—O2−178.94 (10)C15—C16—C17—O5179.04 (10)
C1—C2—C3—C40.37 (18)C15—C16—C17—C18−1.75 (19)
O2—C3—C4—C5178.02 (10)O5—C17—C18—C19−178.74 (10)
C2—C3—C4—C5−1.36 (18)C16—C17—C18—C191.96 (18)
C3—C4—C5—C60.81 (17)C17—C18—C19—C20−0.67 (18)
C4—C5—C6—C8−174.64 (11)C18—C19—C20—C22179.23 (11)
C4—C5—C6—C10.66 (17)C18—C19—C20—C15−0.77 (18)
O1—C1—C6—C8−5.18 (17)O4—C15—C20—C220.43 (19)
C2—C1—C6—C8173.65 (11)C16—C15—C20—C22−179.02 (11)
O1—C1—C6—C5179.58 (11)O4—C15—C20—C19−179.57 (11)
C2—C1—C6—C5−1.58 (16)C16—C15—C20—C190.98 (17)
C9—N1—C8—C6−172.63 (11)C23—N3—C22—C20−177.67 (11)
C5—C6—C8—N1177.35 (11)C19—C20—C22—N3−179.06 (12)
C1—C6—C8—N12.07 (18)C15—C20—C22—N30.94 (19)
C8—N1—C9—C10−112.86 (13)C22—N3—C23—C24102.47 (14)
C11—N2—C10—C9178.68 (11)C28—N4—C24—C23170.73 (10)
C14—N2—C10—C9−59.94 (14)C25—N4—C24—C23−69.17 (13)
N1—C9—C10—N2−171.02 (10)N3—C23—C24—N4−173.15 (10)
C10—N2—C11—C12176.04 (11)C24—N4—C25—C26−178.31 (10)
C14—N2—C11—C1253.07 (15)C28—N4—C25—C26−57.12 (13)
C13—O3—C12—C1159.03 (15)C27—O6—C26—C25−56.66 (13)
N2—C11—C12—O3−55.80 (16)N4—C25—C26—O657.23 (14)
C12—O3—C13—C14−61.84 (15)C26—O6—C27—C2858.34 (13)
C11—N2—C14—C13−54.87 (15)C24—N4—C28—C27−179.29 (10)
C10—N2—C14—C13−175.41 (11)C25—N4—C28—C2758.37 (13)
O3—C13—C14—N260.70 (16)O6—C27—C28—N4−60.28 (14)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O10.88 (1)1.96 (1)2.6489 (15)133 (2)
N1—H1···O1i0.88 (1)2.32 (1)2.9570 (18)129 (1)
N3—H3···O40.89 (1)2.02 (1)2.6930 (15)132 (1)
N3—H3···O4ii0.89 (1)2.29 (1)2.9505 (18)132 (1)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+3, −y, −z−1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2422).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Petek, H., Albayrak, C., İskeleli, N. O., Ağar, E. & Şenel, I. (2005). Acta Cryst. E61, o3990–o3991.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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