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The target complexes, bis­{(E,E)-3,5-bis­[4-(diethyl­amino)­benzyl­idene]-4-oxo­piperidin­ium} butane­dioate, 2C27H36N3O+·C4H4O42-, (II), and bis­{(E,E)-3,5-bis­[4-(diethyl­amino)­benzyl­idene]-4-oxo­piperidin­ium} decane­dioate, 2C27H36N3O+·C10H16O42-, (III), were obtained by solvent-mediated crystallization of the active pharmaceutical ingredient (API) (E,E)-3,5-bis­[4-(diethyl­amino)­benzyl­idene]-4-piperidone and pharmaceutically acceptable dicarb­oxy­lic (succinic and sebacic) acids from ethanol solution. They have been characterized by melting point, IR spectroscopy and single-crystal X-ray diffraction. For the sake of comparison, the structure of the starting API, (E,E)-3,5-bis­[4-(diethyl­amino)­benzyl­idene]-4-piperidone methanol monosolvate, C27H35N3O·CH4O, (I), has also been studied. Compounds (II) and (III) represent salts containing H-shaped centrosymmetric hydrogen-bonded synthons, which are built from two parallel piperidinium cations and a bridging dicarboxyl­ate dianion. In both (II) and (III), the dicarboxyl­ate dianion resides on an inversion centre. The two cations and dianion within the H-shaped synthon are linked by two strong inter­molecular N+-H...-OOC hydrogen bonds. The crystal structure of (II) includes two crystallographically independent formula units, A and B. The cation geometries of units A and B are different. The main N-C6H4-C=C-C(=O)-C=C-C6H4-N back­bone of cation A has a C-shaped conformation, while that of cation B adopts an S-shaped conformation. The same main backbone of the cation in (III) is practically planar. In the crystal structures of both (II) and (III), inter­molecular N+-H...O=C hydrogen bonds between different H-shaped synthons further consolidate the crystal packing, forming columns in the [100] and [10\overline 1] directions, respectively. Salts (II) and (III) possess increased aqueous solubility compared with the original API and thus enhance the bioavailability of the API.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113006185/qs3023sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113006185/qs3023Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113006185/qs3023IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270113006185/qs3023IIIsup4.hkl
Contains datablock III

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113006185/qs3023IIsup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113006185/qs3023IIIsup6.cml
Supplementary material

CCDC references: 934618; 934619; 934620

Computing details top

For all compounds, data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(I) (E,E)-3,5-Bis[4-(diethylamino)benzylidene]-4-piperidone methanol monosolvate top
Crystal data top
C27H35N3O·CH4OF(000) = 976
Mr = 449.62Dx = 1.195 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7753 reflections
a = 14.8473 (5) Åθ = 2.8–30.3°
b = 7.7578 (3) ŵ = 0.08 mm1
c = 21.8602 (7) ÅT = 100 K
β = 96.954 (1)°Plate, red
V = 2499.39 (15) Å30.25 × 0.15 × 0.05 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
6039 independent reflections
Radiation source: fine-focus sealed tube4998 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 28.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1919
Tmin = 0.981, Tmax = 0.996k = 1010
24794 measured reflectionsl = 2827
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: difference Fourier map
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0562P)2 + 0.76P]
where P = (Fo2 + 2Fc2)/3
6039 reflections(Δ/σ)max < 0.001
311 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

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) top
xyzUiso*/Ueq
O10.00038 (6)0.64946 (12)0.42442 (4)0.0264 (2)
N10.15945 (6)0.50058 (13)0.29390 (4)0.0176 (2)
H10.1734 (10)0.609 (2)0.2891 (6)0.025 (4)*
N20.50399 (7)0.36491 (14)0.60934 (5)0.0265 (2)
N30.34302 (6)0.57380 (12)0.09261 (4)0.0184 (2)
C20.19183 (7)0.44718 (14)0.35672 (5)0.0175 (2)
H2A0.25500.48840.36700.021*
H2B0.19320.31960.35810.021*
C30.13620 (7)0.51119 (14)0.40577 (5)0.0165 (2)
C40.04303 (7)0.57945 (14)0.38662 (5)0.0183 (2)
C50.00409 (7)0.55836 (14)0.32113 (5)0.0169 (2)
C60.06224 (7)0.47205 (15)0.27791 (5)0.0180 (2)
H6A0.05030.34650.27780.022*
H6B0.04410.51540.23560.022*
C70.16591 (8)0.51218 (14)0.46674 (5)0.0185 (2)
H70.12230.55100.49200.022*
C80.25284 (8)0.46434 (14)0.50058 (5)0.0181 (2)
C90.32269 (8)0.37078 (14)0.47781 (5)0.0193 (2)
H90.31340.32900.43670.023*
C100.40422 (8)0.33753 (14)0.51311 (5)0.0205 (2)
H100.44940.27360.49570.025*
C110.42215 (8)0.39629 (15)0.57462 (6)0.0213 (2)
C120.35142 (9)0.48654 (16)0.59851 (6)0.0243 (3)
H120.35990.52650.63990.029*
C130.27032 (8)0.51723 (15)0.56236 (6)0.0224 (2)
H130.22400.57700.58010.027*
C140.57408 (8)0.26334 (15)0.58470 (6)0.0226 (2)
H14A0.63340.28880.60870.027*
H14B0.57760.29850.54150.027*
C150.55674 (8)0.07010 (15)0.58652 (6)0.0228 (2)
H15A0.60250.00930.56600.034*
H15B0.49620.04480.56530.034*
H15C0.56030.03190.62950.034*
C160.52166 (9)0.42674 (16)0.67271 (6)0.0253 (3)
H16A0.57280.36040.69440.030*
H16B0.46750.40430.69390.030*
C170.54427 (9)0.61812 (17)0.67766 (6)0.0291 (3)
H17A0.55210.65250.72110.044*
H17B0.49470.68480.65530.044*
H17C0.60050.64020.65970.044*
C180.08113 (8)0.61735 (14)0.30447 (5)0.0185 (2)
H180.10630.67720.33630.022*
C190.14147 (7)0.60650 (14)0.24708 (5)0.0175 (2)
C200.13078 (7)0.50118 (14)0.19586 (5)0.0175 (2)
H200.07740.43340.19660.021*
C210.19492 (7)0.49294 (14)0.14489 (5)0.0176 (2)
H210.18390.42220.11110.021*
C220.27709 (7)0.58768 (14)0.14170 (5)0.0164 (2)
C230.28765 (8)0.69586 (15)0.19233 (5)0.0205 (2)
H230.34080.76450.19170.025*
C240.22217 (8)0.70345 (15)0.24259 (5)0.0214 (2)
H240.23190.77750.27580.026*
C250.33774 (8)0.44712 (15)0.04373 (5)0.0207 (2)
H25A0.39970.40740.02830.025*
H25B0.30260.34600.06090.025*
C260.29326 (10)0.51986 (18)0.00960 (6)0.0309 (3)
H26A0.29120.43090.04120.046*
H26B0.23140.55710.00520.046*
H26C0.32840.61870.02730.046*
C270.42747 (7)0.67278 (15)0.08884 (5)0.0200 (2)
H27A0.45190.68790.04500.024*
H27B0.41430.78860.10670.024*
C280.49906 (8)0.58568 (17)0.12264 (7)0.0282 (3)
H28A0.55490.65420.11750.042*
H28B0.47670.57670.16660.042*
H28C0.51160.47010.10560.042*
O20.24587 (6)0.32664 (11)0.21038 (4)0.02339 (19)
H20.2172 (11)0.381 (2)0.2394 (8)0.041 (5)*
C290.28729 (9)0.45617 (18)0.17799 (6)0.0295 (3)
H29A0.24040.52280.15290.044*
H29B0.32770.40260.15120.044*
H29C0.32250.53290.20740.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0251 (4)0.0340 (5)0.0201 (4)0.0104 (4)0.0022 (3)0.0049 (4)
N10.0173 (5)0.0182 (5)0.0178 (5)0.0008 (4)0.0036 (4)0.0005 (4)
N20.0282 (5)0.0225 (5)0.0258 (6)0.0079 (4)0.0086 (4)0.0080 (4)
N30.0173 (4)0.0208 (5)0.0172 (5)0.0022 (4)0.0022 (4)0.0030 (4)
C20.0163 (5)0.0174 (5)0.0185 (5)0.0007 (4)0.0017 (4)0.0007 (4)
C30.0173 (5)0.0136 (5)0.0188 (6)0.0008 (4)0.0022 (4)0.0006 (4)
C40.0192 (5)0.0161 (5)0.0197 (6)0.0014 (4)0.0027 (4)0.0000 (4)
C50.0195 (5)0.0150 (5)0.0164 (5)0.0009 (4)0.0031 (4)0.0004 (4)
C60.0174 (5)0.0202 (5)0.0166 (5)0.0009 (4)0.0022 (4)0.0011 (4)
C70.0199 (5)0.0150 (5)0.0206 (6)0.0005 (4)0.0029 (4)0.0019 (4)
C80.0205 (5)0.0145 (5)0.0190 (6)0.0006 (4)0.0006 (4)0.0005 (4)
C90.0241 (6)0.0161 (5)0.0172 (5)0.0004 (4)0.0009 (4)0.0008 (4)
C100.0220 (5)0.0165 (5)0.0230 (6)0.0028 (4)0.0020 (5)0.0017 (4)
C110.0249 (6)0.0148 (5)0.0227 (6)0.0017 (4)0.0031 (5)0.0014 (4)
C120.0300 (6)0.0216 (6)0.0198 (6)0.0035 (5)0.0026 (5)0.0050 (5)
C130.0255 (6)0.0200 (6)0.0217 (6)0.0038 (5)0.0020 (5)0.0042 (5)
C140.0198 (5)0.0202 (6)0.0266 (6)0.0005 (4)0.0023 (5)0.0001 (5)
C150.0247 (6)0.0197 (6)0.0242 (6)0.0041 (5)0.0037 (5)0.0002 (5)
C160.0294 (6)0.0224 (6)0.0216 (6)0.0034 (5)0.0070 (5)0.0014 (5)
C170.0289 (6)0.0249 (6)0.0319 (7)0.0005 (5)0.0033 (5)0.0087 (5)
C180.0210 (5)0.0171 (5)0.0178 (5)0.0009 (4)0.0041 (4)0.0016 (4)
C190.0170 (5)0.0173 (5)0.0185 (6)0.0007 (4)0.0034 (4)0.0004 (4)
C200.0158 (5)0.0168 (5)0.0206 (6)0.0023 (4)0.0053 (4)0.0011 (4)
C210.0195 (5)0.0171 (5)0.0172 (5)0.0012 (4)0.0062 (4)0.0007 (4)
C220.0173 (5)0.0158 (5)0.0164 (5)0.0009 (4)0.0030 (4)0.0019 (4)
C230.0181 (5)0.0213 (6)0.0219 (6)0.0057 (4)0.0022 (4)0.0026 (4)
C240.0214 (6)0.0221 (6)0.0208 (6)0.0038 (4)0.0026 (4)0.0051 (5)
C250.0226 (5)0.0207 (6)0.0184 (6)0.0015 (4)0.0013 (4)0.0038 (4)
C260.0444 (8)0.0294 (7)0.0200 (6)0.0103 (6)0.0090 (6)0.0017 (5)
C270.0171 (5)0.0209 (6)0.0217 (6)0.0027 (4)0.0008 (4)0.0009 (4)
C280.0206 (6)0.0278 (7)0.0379 (7)0.0007 (5)0.0098 (5)0.0019 (5)
O20.0279 (4)0.0200 (4)0.0243 (5)0.0013 (3)0.0113 (4)0.0004 (3)
C290.0323 (7)0.0321 (7)0.0258 (7)0.0029 (5)0.0101 (5)0.0057 (5)
Geometric parameters (Å, º) top
O1—C41.2337 (14)C15—H15C0.9800
N1—C21.4590 (14)C16—C171.5231 (18)
N1—C61.4601 (14)C16—H16A0.9900
N1—H10.878 (15)C16—H16B0.9900
N2—C111.3742 (15)C17—H17A0.9800
N2—C141.4594 (16)C17—H17B0.9800
N2—C161.4594 (16)C17—H17C0.9800
N3—C221.3664 (14)C18—C191.4530 (16)
N3—C251.4608 (14)C18—H180.9500
N3—C271.4641 (14)C19—C241.4079 (15)
C2—C31.5144 (15)C19—C201.4105 (15)
C2—H2A0.9900C20—C211.3769 (16)
C2—H2B0.9900C20—H200.9500
C3—C71.3524 (16)C21—C221.4186 (15)
C3—C41.4929 (15)C21—H210.9500
C4—C51.4867 (16)C22—C231.4127 (16)
C5—C181.3535 (16)C23—C241.3774 (16)
C5—C61.5112 (15)C23—H230.9500
C6—H6A0.9900C24—H240.9500
C6—H6B0.9900C25—C261.5167 (17)
C7—C81.4559 (16)C25—H25A0.9900
C7—H70.9500C25—H25B0.9900
C8—C131.4052 (16)C26—H26A0.9800
C8—C91.4054 (16)C26—H26B0.9800
C9—C101.3789 (16)C26—H26C0.9800
C9—H90.9500C27—C281.5238 (16)
C10—C111.4143 (16)C27—H27A0.9900
C10—H100.9500C27—H27B0.9900
C11—C121.4136 (17)C28—H28A0.9800
C12—C131.3787 (17)C28—H28B0.9800
C12—H120.9500C28—H28C0.9800
C13—H130.9500O2—C291.4123 (15)
C14—C151.5224 (17)O2—H20.910 (18)
C14—H14A0.9900C29—H29A0.9800
C14—H14B0.9900C29—H29B0.9800
C15—H15A0.9800C29—H29C0.9800
C15—H15B0.9800
C2—N1—C6112.69 (9)N2—C16—H16A108.8
C2—N1—H1109.3 (9)C17—C16—H16A108.8
C6—N1—H1111.0 (9)N2—C16—H16B108.8
C11—N2—C14120.94 (10)C17—C16—H16B108.8
C11—N2—C16120.75 (10)H16A—C16—H16B107.7
C14—N2—C16118.27 (10)C16—C17—H17A109.5
C22—N3—C25122.05 (9)C16—C17—H17B109.5
C22—N3—C27122.01 (9)H17A—C17—H17B109.5
C25—N3—C27115.67 (9)C16—C17—H17C109.5
N1—C2—C3115.31 (9)H17A—C17—H17C109.5
N1—C2—H2A108.4H17B—C17—H17C109.5
C3—C2—H2A108.4C5—C18—C19132.18 (10)
N1—C2—H2B108.4C5—C18—H18113.9
C3—C2—H2B108.4C19—C18—H18113.9
H2A—C2—H2B107.5C24—C19—C20115.52 (10)
C7—C3—C4117.06 (10)C24—C19—C18117.37 (10)
C7—C3—C2123.98 (10)C20—C19—C18127.01 (10)
C4—C3—C2118.96 (10)C21—C20—C19122.41 (10)
O1—C4—C5121.31 (10)C21—C20—H20118.8
O1—C4—C3120.65 (10)C19—C20—H20118.8
C5—C4—C3118.03 (9)C20—C21—C22121.47 (10)
C18—C5—C4117.64 (10)C20—C21—H21119.3
C18—C5—C6124.60 (10)C22—C21—H21119.3
C4—C5—C6117.76 (9)N3—C22—C23121.68 (10)
N1—C6—C5113.96 (9)N3—C22—C21121.85 (10)
N1—C6—H6A108.8C23—C22—C21116.47 (10)
C5—C6—H6A108.8C24—C23—C22121.04 (10)
N1—C6—H6B108.8C24—C23—H23119.5
C5—C6—H6B108.8C22—C23—H23119.5
H6A—C6—H6B107.7C23—C24—C19123.04 (11)
C3—C7—C8131.50 (11)C23—C24—H24118.5
C3—C7—H7114.3C19—C24—H24118.5
C8—C7—H7114.3N3—C25—C26112.27 (10)
C13—C8—C9115.65 (10)N3—C25—H25A109.2
C13—C8—C7117.59 (10)C26—C25—H25A109.2
C9—C8—C7126.76 (10)N3—C25—H25B109.2
C10—C9—C8122.27 (11)C26—C25—H25B109.2
C10—C9—H9118.9H25A—C25—H25B107.9
C8—C9—H9118.9C25—C26—H26A109.5
C9—C10—C11121.55 (11)C25—C26—H26B109.5
C9—C10—H10119.2H26A—C26—H26B109.5
C11—C10—H10119.2C25—C26—H26C109.5
N2—C11—C12122.03 (11)H26A—C26—H26C109.5
N2—C11—C10121.34 (11)H26B—C26—H26C109.5
C12—C11—C10116.62 (10)N3—C27—C28112.52 (10)
C13—C12—C11120.67 (11)N3—C27—H27A109.1
C13—C12—H12119.7C28—C27—H27A109.1
C11—C12—H12119.7N3—C27—H27B109.1
C12—C13—C8123.18 (11)C28—C27—H27B109.1
C12—C13—H13118.4H27A—C27—H27B107.8
C8—C13—H13118.4C27—C28—H28A109.5
N2—C14—C15113.05 (10)C27—C28—H28B109.5
N2—C14—H14A109.0H28A—C28—H28B109.5
C15—C14—H14A109.0C27—C28—H28C109.5
N2—C14—H14B109.0H28A—C28—H28C109.5
C15—C14—H14B109.0H28B—C28—H28C109.5
H14A—C14—H14B107.8C29—O2—H2106.7 (11)
C14—C15—H15A109.5O2—C29—H29A109.5
C14—C15—H15B109.5O2—C29—H29B109.5
H15A—C15—H15B109.5H29A—C29—H29B109.5
C14—C15—H15C109.5O2—C29—H29C109.5
H15A—C15—H15C109.5H29A—C29—H29C109.5
H15B—C15—H15C109.5H29B—C29—H29C109.5
N2—C16—C17113.61 (11)
C6—N1—C2—C348.39 (13)C11—C12—C13—C80.77 (19)
N1—C2—C3—C7163.33 (10)C9—C8—C13—C122.36 (18)
N1—C2—C3—C416.07 (14)C7—C8—C13—C12177.14 (11)
C7—C3—C4—O17.25 (16)C11—N2—C14—C1578.79 (15)
C2—C3—C4—O1172.19 (11)C16—N2—C14—C1598.87 (13)
C7—C3—C4—C5171.98 (10)C11—N2—C16—C1777.86 (15)
C2—C3—C4—C58.58 (15)C14—N2—C16—C17104.48 (13)
O1—C4—C5—C180.59 (17)C4—C5—C18—C19174.55 (11)
C3—C4—C5—C18178.64 (10)C6—C5—C18—C195.2 (2)
O1—C4—C5—C6179.64 (11)C5—C18—C19—C24171.40 (12)
C3—C4—C5—C61.14 (15)C5—C18—C19—C2012.4 (2)
C2—N1—C6—C556.02 (13)C24—C19—C20—C210.20 (16)
C18—C5—C6—N1149.39 (11)C18—C19—C20—C21176.03 (11)
C4—C5—C6—N130.85 (14)C19—C20—C21—C221.57 (17)
C4—C3—C7—C8176.56 (11)C25—N3—C22—C23172.35 (10)
C2—C3—C7—C82.9 (2)C27—N3—C22—C231.40 (16)
C3—C7—C8—C13165.37 (12)C25—N3—C22—C216.93 (16)
C3—C7—C8—C914.1 (2)C27—N3—C22—C21179.31 (10)
C13—C8—C9—C101.95 (17)C20—C21—C22—N3176.75 (10)
C7—C8—C9—C10177.50 (11)C20—C21—C22—C232.57 (16)
C8—C9—C10—C110.03 (18)N3—C22—C23—C24177.42 (11)
C14—N2—C11—C12176.63 (11)C21—C22—C23—C241.90 (17)
C16—N2—C11—C120.96 (18)C22—C23—C24—C190.20 (19)
C14—N2—C11—C102.58 (18)C20—C19—C24—C230.88 (17)
C16—N2—C11—C10179.82 (11)C18—C19—C24—C23175.72 (11)
C9—C10—C11—N2179.08 (11)C22—N3—C25—C2692.64 (13)
C9—C10—C11—C121.67 (17)C27—N3—C25—C2693.24 (12)
N2—C11—C12—C13179.47 (12)C22—N3—C27—C2884.62 (13)
C10—C11—C12—C131.28 (18)C25—N3—C27—C2889.50 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.878 (15)2.068 (15)2.9009 (13)158.1 (13)
O2—H2···N10.910 (18)1.806 (18)2.7144 (13)176.4 (16)
Symmetry code: (i) x+1/2, y+1/2, z+1/2.
(II) Bis{(E,E)-3,5-bis[4-(diethylamino)benzylidene]-4-oxopiperidinium} butanedioate top
Crystal data top
2C27H36N3O+·C4H4O42Z = 2
Mr = 953.27F(000) = 1028
Triclinic, P1Dx = 1.244 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.1075 (15) ÅCell parameters from 4344 reflections
b = 12.9650 (18) Åθ = 2.2–30.4°
c = 17.899 (3) ŵ = 0.08 mm1
α = 96.320 (3)°T = 100 K
β = 92.211 (3)°Prism, yellow
γ = 95.861 (3)°0.30 × 0.20 × 0.10 mm
V = 2545.3 (7) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
9952 independent reflections
Radiation source: fine-focus sealed tube6795 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1313
Tmin = 0.976, Tmax = 0.992k = 1515
16330 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0897P)2 + 1.4P]
where P = (Fo2 + 2Fc2)/3
9952 reflections(Δ/σ)max < 0.001
647 parametersΔρmax = 0.56 e Å3
6 restraintsΔρmin = 0.52 e Å3
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
O1A1.08996 (17)0.70377 (16)0.87565 (11)0.0340 (5)
N1A0.8329 (2)0.65779 (18)0.70200 (12)0.0292 (5)
H1A0.78420.69120.73350.035*
H1B0.79480.63580.65490.035*
N2A1.2124 (4)1.1885 (2)0.60754 (14)0.0719 (12)
N3A0.60699 (19)0.18989 (18)0.94333 (12)0.0274 (5)
C2A0.9450 (2)0.7225 (2)0.68893 (14)0.0283 (6)
H2A0.92370.78590.66750.034*
H2B0.99120.68300.65140.034*
C3A1.0241 (2)0.7545 (2)0.75943 (15)0.0249 (6)
C4A1.0192 (2)0.6846 (2)0.81997 (15)0.0256 (6)
C5A0.9263 (2)0.5930 (2)0.81242 (14)0.0241 (6)
C6A0.8555 (3)0.5653 (2)0.73858 (15)0.0302 (6)
H6A0.90070.51940.70470.036*
H6B0.77700.52600.74710.036*
C7A1.0967 (2)0.8454 (2)0.77244 (15)0.0263 (6)
H7A1.13710.85650.82090.032*
C8A1.1246 (2)0.9290 (2)0.72648 (15)0.0270 (6)
C9A1.1204 (3)0.9191 (2)0.64753 (17)0.0392 (7)
H9A1.09620.85260.62030.047*
C10A1.1502 (4)1.0027 (3)0.60840 (18)0.0497 (9)
H10A1.14590.99260.55490.060*
C11A1.1873 (3)1.1039 (2)0.64603 (17)0.0428 (8)
C12A1.1943 (2)1.1130 (2)0.72471 (16)0.0314 (6)
H12A1.21971.17890.75240.038*
C13A1.1651 (2)1.0283 (2)0.76219 (16)0.0292 (6)
H13A1.17271.03760.81560.035*
C14A1.1806 (3)1.1851 (4)0.52497 (19)0.0368 (11)0.631 (6)
H14A1.15831.25390.51370.044*0.631 (6)
H14B1.11031.13240.51040.044*0.631 (6)
C15A1.2895 (4)1.1568 (4)0.4801 (2)0.0472 (13)0.631 (6)
H15A1.26691.14920.42620.071*0.631 (6)
H15B1.31481.09090.49400.071*0.631 (6)
H15C1.35661.21220.49150.071*0.631 (6)
C14C1.2712 (5)1.1664 (6)0.5353 (2)0.0368 (11)0.37
H14E1.30341.09770.53320.044*0.369 (6)
H14F1.33981.22040.53150.044*0.369 (6)
C15C1.1780 (7)1.1659 (8)0.4696 (2)0.0472 (13)0.37
H15G1.21521.14680.42200.071*0.369 (6)
H15H1.15101.23550.46960.071*0.369 (6)
H15I1.10831.11510.47520.071*0.369 (6)
C16A1.2574 (3)1.2909 (2)0.64667 (18)0.0423 (8)
H16A1.21041.30380.69200.051*
H16B1.24181.34470.61340.051*
C17A1.3906 (3)1.3044 (3)0.6704 (2)0.0558 (10)
H17A1.41211.37430.69740.084*
H17B1.43861.29610.62580.084*
H17C1.40751.25170.70360.084*
C18A0.9078 (2)0.5437 (2)0.87439 (15)0.0273 (6)
H18A0.95720.57370.91740.033*
C19A0.8261 (2)0.4532 (2)0.88704 (14)0.0261 (6)
C20A0.7762 (2)0.3734 (2)0.83172 (15)0.0294 (6)
H20A0.79310.37850.78050.035*
C21A0.7038 (2)0.2881 (2)0.84951 (15)0.0292 (6)
H21A0.67240.23560.81040.035*
C22A0.6751 (2)0.2763 (2)0.92421 (15)0.0247 (6)
C23A0.7251 (2)0.3564 (2)0.98010 (15)0.0249 (6)
H23A0.70770.35211.03130.030*
C24A0.7982 (2)0.4401 (2)0.96141 (14)0.0245 (6)
H24A0.83170.49161.00060.029*
C25A0.5669 (2)0.1008 (2)0.88766 (16)0.0305 (6)
H25A0.55600.03700.91350.037*
H25B0.63100.09160.85130.037*
C26A0.4494 (3)0.1125 (3)0.84498 (17)0.0391 (7)
H26A0.42500.04900.81060.059*
H26B0.46130.17230.81600.059*
H26C0.38610.12380.88070.059*
C27A0.5607 (2)0.1861 (2)1.01812 (15)0.0269 (6)
H27A0.48140.14301.01370.032*
H27B0.54720.25761.03920.032*
C28A0.6443 (2)0.1420 (2)1.07231 (16)0.0308 (6)
H28A0.60630.13881.12060.046*
H28B0.72120.18701.07990.046*
H28C0.65950.07171.05150.046*
O2A0.74229 (17)0.58814 (18)0.57166 (11)0.0394 (5)
O3A0.57358 (18)0.5652 (2)0.63151 (11)0.0486 (6)
C29A0.6289 (2)0.5587 (2)0.57354 (14)0.0268 (6)
C30A0.5680 (2)0.5105 (2)0.49952 (15)0.0305 (6)
H30A0.60150.44380.48450.037*
H30B0.58820.55750.46080.037*
O1B0.36751 (17)0.34005 (17)0.15765 (12)0.0404 (5)
N1B0.63635 (19)0.35149 (17)0.31356 (11)0.0240 (5)
H1C0.58220.38910.33720.029*
H1D0.70040.35390.34940.029*
N2B0.2396 (2)0.16004 (19)0.40590 (14)0.0355 (6)
N3B0.90546 (19)0.76950 (18)0.02450 (13)0.0298 (5)
C2B0.5783 (2)0.2450 (2)0.29200 (15)0.0268 (6)
H2C0.55310.21400.33780.032*
H2D0.63780.20200.26770.032*
C3B0.4693 (2)0.2427 (2)0.23874 (14)0.0238 (6)
C4B0.4620 (2)0.3319 (2)0.19360 (15)0.0266 (6)
C5B0.5710 (2)0.4086 (2)0.19306 (14)0.0233 (5)
C6B0.6763 (2)0.4015 (2)0.24740 (14)0.0245 (6)
H6C0.73630.36070.22150.029*
H6D0.71640.47250.26410.029*
C7B0.3743 (2)0.1687 (2)0.23265 (14)0.0230 (5)
H7B0.31380.17710.19540.028*
C8B0.3476 (2)0.0785 (2)0.27265 (14)0.0245 (6)
C9B0.4326 (2)0.0286 (2)0.31196 (15)0.0269 (6)
H9B0.51650.05090.31000.032*
C10B0.3976 (2)0.0510 (2)0.35273 (16)0.0291 (6)
H10B0.45800.08390.37730.035*
C11B0.2739 (2)0.0864 (2)0.35979 (15)0.0291 (6)
C12B0.1891 (2)0.0404 (2)0.31694 (15)0.0300 (6)
H12B0.10530.06400.31730.036*
C13B0.2259 (2)0.0378 (2)0.27498 (15)0.0262 (6)
H13B0.16640.06590.24600.031*
C14B0.3279 (3)0.2195 (3)0.43982 (19)0.0419 (8)
H14C0.39330.23030.40460.050*
H14D0.28770.28890.44760.050*
C15B0.3832 (3)0.1653 (3)0.51439 (19)0.0540 (10)
H15D0.44390.20670.53380.081*
H15E0.31950.15820.55050.081*
H15F0.42190.09600.50720.081*
C16B0.1130 (3)0.1993 (2)0.41177 (16)0.0341 (7)
H16C0.06230.14090.41010.041*
H16D0.10310.22670.46090.041*
C17B0.0692 (3)0.2850 (3)0.34902 (18)0.0462 (8)
H17D0.01250.31510.35870.069*
H17E0.12440.33950.34700.069*
H17F0.06750.25560.30090.069*
C18B0.5682 (2)0.4784 (2)0.14258 (14)0.0241 (6)
H18B0.49180.47570.11620.029*
C19B0.6584 (2)0.5569 (2)0.12043 (14)0.0232 (5)
C20B0.7802 (2)0.5779 (2)0.14715 (14)0.0242 (6)
H20B0.80860.54090.18610.029*
C21B0.8595 (2)0.6505 (2)0.11854 (14)0.0246 (6)
H21B0.94000.66470.13990.029*
C22B0.8243 (2)0.7046 (2)0.05833 (15)0.0257 (6)
C23B0.7015 (2)0.6851 (2)0.03169 (16)0.0273 (6)
H23B0.67310.72110.00780.033*
C24B0.6229 (2)0.6140 (2)0.06267 (15)0.0260 (6)
H24B0.54080.60320.04400.031*
C25B1.0324 (2)0.7902 (2)0.05277 (16)0.0289 (6)
H25C1.08220.81340.01180.035*
H25D1.06030.72410.06610.035*
C26B1.0547 (3)0.8715 (2)0.12062 (17)0.0361 (7)
H26D1.14150.88240.13490.054*
H26E1.00980.84750.16260.054*
H26F1.02710.93730.10820.054*
C27B0.8677 (2)0.8222 (2)0.03969 (16)0.0308 (6)
H27C0.81020.77330.07350.037*
H27D0.93950.84110.06840.037*
C28B0.8084 (3)0.9193 (2)0.01591 (19)0.0406 (8)
H28D0.77960.94860.06070.061*
H28E0.86730.97080.01360.061*
H28F0.73960.90170.01480.061*
O2B0.80151 (16)0.35015 (15)0.41720 (10)0.0305 (4)
O3B0.87862 (18)0.49971 (16)0.38002 (11)0.0380 (5)
C29B0.8752 (2)0.4360 (2)0.42502 (14)0.0241 (6)
C30B0.9598 (2)0.4489 (2)0.49504 (15)0.0254 (6)
H30C0.91070.44430.53980.030*
H30D1.01120.39080.49210.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0239 (10)0.0401 (12)0.0363 (11)0.0053 (9)0.0094 (8)0.0088 (9)
N1A0.0239 (12)0.0356 (13)0.0258 (12)0.0019 (10)0.0065 (9)0.0034 (10)
N2A0.147 (3)0.0305 (16)0.0324 (15)0.0212 (19)0.0272 (18)0.0022 (12)
N3A0.0221 (11)0.0302 (13)0.0273 (12)0.0036 (10)0.0024 (9)0.0007 (10)
C2A0.0315 (15)0.0276 (15)0.0240 (13)0.0000 (12)0.0023 (11)0.0005 (11)
C3A0.0152 (12)0.0293 (15)0.0291 (14)0.0030 (11)0.0009 (10)0.0007 (11)
C4A0.0151 (12)0.0312 (15)0.0300 (14)0.0037 (11)0.0017 (11)0.0005 (12)
C5A0.0191 (12)0.0274 (14)0.0250 (13)0.0032 (11)0.0022 (10)0.0002 (11)
C6A0.0284 (14)0.0316 (15)0.0286 (14)0.0030 (12)0.0049 (11)0.0026 (12)
C7A0.0162 (12)0.0330 (15)0.0293 (14)0.0049 (11)0.0023 (10)0.0007 (12)
C8A0.0189 (13)0.0286 (15)0.0332 (15)0.0023 (11)0.0022 (11)0.0018 (12)
C9A0.0531 (19)0.0292 (16)0.0331 (16)0.0003 (14)0.0115 (14)0.0055 (13)
C10A0.081 (3)0.0347 (18)0.0303 (16)0.0048 (17)0.0196 (17)0.0047 (14)
C11A0.064 (2)0.0258 (16)0.0375 (17)0.0021 (15)0.0169 (15)0.0015 (13)
C12A0.0294 (15)0.0287 (15)0.0344 (15)0.0004 (12)0.0040 (12)0.0015 (12)
C13A0.0197 (13)0.0369 (16)0.0300 (14)0.0024 (12)0.0000 (11)0.0009 (12)
C14A0.034 (2)0.027 (2)0.053 (3)0.0108 (19)0.011 (2)0.009 (2)
C15A0.040 (2)0.048 (3)0.054 (3)0.008 (2)0.011 (2)0.003 (2)
C14C0.034 (2)0.027 (2)0.053 (3)0.0108 (19)0.011 (2)0.009 (2)
C15C0.040 (2)0.048 (3)0.054 (3)0.008 (2)0.011 (2)0.003 (2)
C16A0.062 (2)0.0228 (15)0.0422 (18)0.0020 (15)0.0106 (16)0.0026 (13)
C17A0.053 (2)0.051 (2)0.071 (2)0.0193 (18)0.0223 (19)0.0219 (19)
C18A0.0182 (12)0.0329 (15)0.0297 (14)0.0040 (11)0.0021 (11)0.0006 (12)
C19A0.0223 (13)0.0297 (15)0.0260 (13)0.0039 (11)0.0022 (11)0.0025 (11)
C20A0.0295 (14)0.0328 (16)0.0250 (14)0.0024 (12)0.0020 (11)0.0006 (12)
C21A0.0255 (14)0.0316 (15)0.0280 (14)0.0009 (12)0.0026 (11)0.0029 (12)
C22A0.0167 (12)0.0266 (14)0.0303 (14)0.0023 (11)0.0023 (10)0.0019 (11)
C23A0.0195 (12)0.0290 (15)0.0260 (13)0.0041 (11)0.0002 (10)0.0014 (11)
C24A0.0214 (13)0.0252 (14)0.0261 (13)0.0043 (11)0.0018 (10)0.0019 (11)
C25A0.0260 (14)0.0302 (15)0.0322 (15)0.0033 (12)0.0004 (11)0.0033 (12)
C26A0.0244 (15)0.054 (2)0.0343 (16)0.0041 (14)0.0064 (12)0.0033 (14)
C27A0.0177 (12)0.0297 (15)0.0323 (14)0.0005 (11)0.0001 (11)0.0024 (12)
C28A0.0267 (14)0.0331 (16)0.0317 (15)0.0003 (12)0.0032 (12)0.0041 (12)
O2A0.0222 (10)0.0596 (14)0.0315 (11)0.0077 (10)0.0046 (8)0.0029 (10)
O3A0.0278 (11)0.0831 (18)0.0288 (11)0.0009 (11)0.0009 (9)0.0151 (11)
C29A0.0248 (14)0.0300 (15)0.0246 (14)0.0019 (11)0.0025 (11)0.0002 (11)
C30A0.0248 (14)0.0415 (17)0.0226 (13)0.0006 (12)0.0020 (11)0.0024 (12)
O1B0.0233 (10)0.0426 (13)0.0546 (13)0.0082 (9)0.0168 (9)0.0191 (10)
N1B0.0180 (10)0.0314 (12)0.0204 (11)0.0035 (9)0.0046 (8)0.0014 (9)
N2B0.0313 (13)0.0332 (14)0.0426 (14)0.0010 (11)0.0008 (11)0.0116 (11)
N3B0.0183 (11)0.0329 (13)0.0390 (13)0.0006 (10)0.0024 (10)0.0122 (11)
C2B0.0239 (13)0.0274 (14)0.0280 (14)0.0030 (11)0.0040 (11)0.0053 (11)
C3B0.0195 (12)0.0292 (14)0.0219 (13)0.0012 (11)0.0012 (10)0.0011 (11)
C4B0.0198 (13)0.0316 (15)0.0269 (14)0.0001 (11)0.0009 (11)0.0008 (11)
C5B0.0182 (12)0.0264 (14)0.0243 (13)0.0001 (11)0.0007 (10)0.0012 (11)
C6B0.0182 (12)0.0310 (15)0.0231 (13)0.0018 (11)0.0017 (10)0.0030 (11)
C7B0.0196 (12)0.0278 (14)0.0202 (12)0.0024 (11)0.0000 (10)0.0034 (10)
C8B0.0242 (13)0.0263 (14)0.0201 (12)0.0037 (11)0.0003 (10)0.0032 (10)
C9B0.0212 (13)0.0301 (15)0.0279 (14)0.0007 (11)0.0004 (11)0.0008 (11)
C10B0.0254 (14)0.0266 (15)0.0348 (15)0.0040 (12)0.0006 (12)0.0012 (12)
C11B0.0301 (15)0.0262 (14)0.0295 (14)0.0018 (12)0.0012 (11)0.0018 (11)
C12B0.0238 (14)0.0313 (15)0.0319 (15)0.0073 (12)0.0041 (11)0.0012 (12)
C13B0.0254 (14)0.0239 (14)0.0274 (14)0.0006 (11)0.0039 (11)0.0017 (11)
C14B0.0388 (17)0.0380 (18)0.054 (2)0.0086 (14)0.0091 (15)0.0212 (15)
C15B0.0351 (18)0.084 (3)0.049 (2)0.0098 (18)0.0050 (15)0.0279 (19)
C16B0.0328 (15)0.0320 (16)0.0374 (16)0.0021 (13)0.0052 (13)0.0075 (13)
C17B0.054 (2)0.0392 (19)0.0419 (18)0.0129 (16)0.0023 (15)0.0069 (15)
C18B0.0158 (12)0.0288 (14)0.0259 (13)0.0010 (11)0.0031 (10)0.0019 (11)
C19B0.0212 (13)0.0224 (13)0.0252 (13)0.0028 (11)0.0005 (10)0.0002 (10)
C20B0.0210 (13)0.0286 (14)0.0221 (13)0.0020 (11)0.0015 (10)0.0005 (11)
C21B0.0184 (12)0.0277 (14)0.0266 (13)0.0020 (11)0.0010 (10)0.0003 (11)
C22B0.0208 (13)0.0256 (14)0.0305 (14)0.0023 (11)0.0010 (11)0.0023 (11)
C23B0.0202 (13)0.0259 (14)0.0367 (15)0.0028 (11)0.0042 (11)0.0099 (12)
C24B0.0162 (12)0.0288 (15)0.0330 (14)0.0033 (11)0.0043 (11)0.0046 (12)
C25B0.0180 (13)0.0324 (15)0.0362 (15)0.0014 (11)0.0002 (11)0.0076 (12)
C26B0.0290 (15)0.0345 (17)0.0433 (17)0.0002 (13)0.0022 (13)0.0007 (13)
C27B0.0236 (14)0.0341 (16)0.0352 (15)0.0008 (12)0.0027 (12)0.0071 (13)
C28B0.0295 (16)0.0354 (17)0.058 (2)0.0028 (13)0.0056 (14)0.0123 (15)
O2B0.0264 (10)0.0300 (11)0.0328 (10)0.0068 (8)0.0099 (8)0.0065 (8)
O3B0.0379 (12)0.0343 (12)0.0389 (12)0.0103 (9)0.0150 (9)0.0113 (9)
C29B0.0177 (12)0.0269 (14)0.0271 (14)0.0003 (11)0.0013 (10)0.0038 (11)
C30B0.0219 (13)0.0256 (14)0.0275 (14)0.0010 (11)0.0053 (11)0.0034 (11)
Geometric parameters (Å, º) top
O1A—C4A1.232 (3)C30A—C30Ai1.508 (5)
N1A—C6A1.466 (4)C30A—H30A0.9900
N1A—C2A1.470 (3)C30A—H30B0.9900
N1A—H1A0.9030O1B—C4B1.230 (3)
N1A—H1B0.9300N1B—C2B1.466 (3)
N2A—C11A1.369 (4)N1B—C6B1.473 (3)
N2A—C16A1.462 (4)N1B—H1C0.9010
N2A—C14C1.485 (3)N1B—H1D0.9361
N2A—C14A1.501 (3)N2B—C11B1.364 (4)
N3A—C22A1.370 (3)N2B—C16B1.457 (4)
N3A—C27A1.456 (3)N2B—C14B1.461 (4)
N3A—C25A1.461 (3)N3B—C22B1.373 (3)
C2A—C3A1.504 (4)N3B—C25B1.468 (3)
C2A—H2A0.9900N3B—C27B1.469 (3)
C2A—H2B0.9900C2B—C3B1.508 (4)
C3A—C7A1.351 (4)C2B—H2C0.9900
C3A—C4A1.487 (4)C2B—H2D0.9900
C4A—C5A1.482 (4)C3B—C7B1.344 (4)
C5A—C18A1.352 (4)C3B—C4B1.488 (4)
C5A—C6A1.501 (4)C4B—C5B1.487 (3)
C6A—H6A0.9900C5B—C18B1.350 (4)
C6A—H6B0.9900C5B—C6B1.509 (3)
C7A—C8A1.447 (4)C6B—H6C0.9900
C7A—H7A0.9500C6B—H6D0.9900
C8A—C13A1.395 (4)C7B—C8B1.449 (4)
C8A—C9A1.403 (4)C7B—H7B0.9500
C9A—C10A1.374 (4)C8B—C13B1.404 (4)
C9A—H9A0.9500C8B—C9B1.407 (4)
C10A—C11A1.421 (4)C9B—C10B1.362 (4)
C10A—H10A0.9500C9B—H9B0.9500
C11A—C12A1.399 (4)C10B—C11B1.418 (4)
C12A—C13A1.367 (4)C10B—H10B0.9500
C12A—H12A0.9500C11B—C12B1.411 (4)
C13A—H13A0.9500C12B—C13B1.365 (4)
C14A—C15A1.530 (3)C12B—H12B0.9500
C14A—H14A0.9900C13B—H13B0.9500
C14A—H14B0.9900C14B—C15B1.515 (5)
C15A—H15A0.9800C14B—H14C0.9900
C15A—H15B0.9800C14B—H14D0.9900
C15A—H15C0.9800C15B—H15D0.9800
C14C—C15C1.536 (3)C15B—H15E0.9800
C14C—H14E0.9900C15B—H15F0.9800
C14C—H14F0.9900C16B—C17B1.519 (4)
C15C—H15G0.9800C16B—H16C0.9900
C15C—H15H0.9800C16B—H16D0.9900
C15C—H15I0.9800C17B—H17D0.9800
C16A—C17A1.510 (5)C17B—H17E0.9800
C16A—H16A0.9900C17B—H17F0.9800
C16A—H16B0.9900C18B—C19B1.451 (3)
C17A—H17A0.9800C18B—H18B0.9500
C17A—H17B0.9800C19B—C24B1.404 (4)
C17A—H17C0.9800C19B—C20B1.407 (3)
C18A—C19A1.453 (4)C20B—C21B1.377 (4)
C18A—H18A0.9500C20B—H20B0.9500
C19A—C24A1.403 (4)C21B—C22B1.413 (4)
C19A—C20A1.405 (4)C21B—H21B0.9500
C20A—C21A1.374 (4)C22B—C23B1.416 (4)
C20A—H20A0.9500C23B—C24B1.380 (4)
C21A—C22A1.407 (4)C23B—H23B0.9500
C21A—H21A0.9500C24B—H24B0.9500
C22A—C23A1.414 (4)C25B—C26B1.513 (4)
C23A—C24A1.367 (4)C25B—H25C0.9900
C23A—H23A0.9500C25B—H25D0.9900
C24A—H24A0.9500C26B—H26D0.9800
C25A—C26A1.516 (4)C26B—H26E0.9800
C25A—H25A0.9900C26B—H26F0.9800
C25A—H25B0.9900C27B—C28B1.508 (4)
C26A—H26A0.9800C27B—H27C0.9900
C26A—H26B0.9800C27B—H27D0.9900
C26A—H26C0.9800C28B—H28D0.9800
C27A—C28A1.513 (4)C28B—H28E0.9800
C27A—H27A0.9900C28B—H28F0.9800
C27A—H27B0.9900O2B—C29B1.304 (3)
C28A—H28A0.9800O3B—C29B1.214 (3)
C28A—H28B0.9800C29B—C30B1.521 (4)
C28A—H28C0.9800C30B—C30Bii1.510 (5)
O2A—C29A1.281 (3)C30B—H30C0.9900
O3A—C29A1.226 (3)C30B—H30D0.9900
C29A—C30A1.505 (4)
C6A—N1A—C2A112.8 (2)C30Ai—C30A—H30A108.7
C6A—N1A—H1A103.7C29A—C30A—H30B108.7
C2A—N1A—H1A113.2C30Ai—C30A—H30B108.7
C6A—N1A—H1B108.5H30A—C30A—H30B107.6
C2A—N1A—H1B106.5C2B—N1B—C6B111.6 (2)
H1A—N1A—H1B112.2C2B—N1B—H1C108.3
C11A—N2A—C16A121.4 (3)C6B—N1B—H1C109.1
C11A—N2A—C14C115.0 (4)C2B—N1B—H1D112.4
C16A—N2A—C14C112.1 (4)C6B—N1B—H1D110.9
C11A—N2A—C14A122.1 (3)H1C—N1B—H1D104.2
C16A—N2A—C14A116.0 (3)C11B—N2B—C16B122.0 (2)
C22A—N3A—C27A121.8 (2)C11B—N2B—C14B121.4 (2)
C22A—N3A—C25A121.6 (2)C16B—N2B—C14B115.3 (2)
C27A—N3A—C25A116.3 (2)C22B—N3B—C25B120.8 (2)
N1A—C2A—C3A112.9 (2)C22B—N3B—C27B121.3 (2)
N1A—C2A—H2A109.0C25B—N3B—C27B117.9 (2)
C3A—C2A—H2A109.0N1B—C2B—C3B112.0 (2)
N1A—C2A—H2B109.0N1B—C2B—H2C109.2
C3A—C2A—H2B109.0C3B—C2B—H2C109.2
H2A—C2A—H2B107.8N1B—C2B—H2D109.2
C7A—C3A—C4A117.6 (2)C3B—C2B—H2D109.2
C7A—C3A—C2A123.8 (2)H2C—C2B—H2D107.9
C4A—C3A—C2A118.6 (2)C7B—C3B—C4B117.5 (2)
O1A—C4A—C5A121.1 (2)C7B—C3B—C2B124.4 (2)
O1A—C4A—C3A120.3 (2)C4B—C3B—C2B118.0 (2)
C5A—C4A—C3A118.6 (2)O1B—C4B—C5B121.8 (2)
C18A—C5A—C4A116.9 (2)O1B—C4B—C3B119.7 (2)
C18A—C5A—C6A124.9 (2)C5B—C4B—C3B118.4 (2)
C4A—C5A—C6A118.1 (2)C18B—C5B—C4B116.8 (2)
N1A—C6A—C5A112.3 (2)C18B—C5B—C6B125.1 (2)
N1A—C6A—H6A109.1C4B—C5B—C6B118.1 (2)
C5A—C6A—H6A109.1N1B—C6B—C5B111.4 (2)
N1A—C6A—H6B109.1N1B—C6B—H6C109.4
C5A—C6A—H6B109.1C5B—C6B—H6C109.4
H6A—C6A—H6B107.9N1B—C6B—H6D109.4
C3A—C7A—C8A132.1 (3)C5B—C6B—H6D109.4
C3A—C7A—H7A113.9H6C—C6B—H6D108.0
C8A—C7A—H7A113.9C3B—C7B—C8B131.5 (2)
C13A—C8A—C9A115.5 (3)C3B—C7B—H7B114.2
C13A—C8A—C7A118.6 (2)C8B—C7B—H7B114.2
C9A—C8A—C7A125.9 (3)C13B—C8B—C9B116.0 (2)
C10A—C9A—C8A121.9 (3)C13B—C8B—C7B118.0 (2)
C10A—C9A—H9A119.0C9B—C8B—C7B126.0 (2)
C8A—C9A—H9A119.0C10B—C9B—C8B121.6 (2)
C9A—C10A—C11A121.5 (3)C10B—C9B—H9B119.2
C9A—C10A—H10A119.2C8B—C9B—H9B119.2
C11A—C10A—H10A119.2C9B—C10B—C11B122.2 (3)
N2A—C11A—C12A121.6 (3)C9B—C10B—H10B118.9
N2A—C11A—C10A121.9 (3)C11B—C10B—H10B118.9
C12A—C11A—C10A116.4 (3)N2B—C11B—C12B122.3 (2)
C13A—C12A—C11A120.8 (3)N2B—C11B—C10B121.6 (3)
C13A—C12A—H12A119.6C12B—C11B—C10B116.1 (2)
C11A—C12A—H12A119.6C13B—C12B—C11B120.8 (2)
C12A—C13A—C8A123.8 (3)C13B—C12B—H12B119.6
C12A—C13A—H13A118.1C11B—C12B—H12B119.6
C8A—C13A—H13A118.1C12B—C13B—C8B123.1 (3)
N2A—C14A—C15A109.4 (2)C12B—C13B—H13B118.5
N2A—C14A—H14A109.8C8B—C13B—H13B118.5
C15A—C14A—H14A109.8N2B—C14B—C15B112.6 (3)
N2A—C14A—H14B109.8N2B—C14B—H14C109.1
C15A—C14A—H14B109.8C15B—C14B—H14C109.1
H14A—C14A—H14B108.2N2B—C14B—H14D109.1
N2A—C14C—C15C109.4 (3)C15B—C14B—H14D109.1
N2A—C14C—H14E109.8H14C—C14B—H14D107.8
C15C—C14C—H14E109.8C14B—C15B—H15D109.5
N2A—C14C—H14F109.8C14B—C15B—H15E109.5
C15C—C14C—H14F109.8H15D—C15B—H15E109.5
H14E—C14C—H14F108.2C14B—C15B—H15F109.5
C14C—C15C—H15G109.5H15D—C15B—H15F109.5
C14C—C15C—H15H109.5H15E—C15B—H15F109.5
H15G—C15C—H15H109.5N2B—C16B—C17B112.2 (3)
C14C—C15C—H15I109.5N2B—C16B—H16C109.2
H15G—C15C—H15I109.5C17B—C16B—H16C109.2
H15H—C15C—H15I109.5N2B—C16B—H16D109.2
N2A—C16A—C17A115.1 (3)C17B—C16B—H16D109.2
N2A—C16A—H16A108.5H16C—C16B—H16D107.9
C17A—C16A—H16A108.5C16B—C17B—H17D109.5
N2A—C16A—H16B108.5C16B—C17B—H17E109.5
C17A—C16A—H16B108.5H17D—C17B—H17E109.5
H16A—C16A—H16B107.5C16B—C17B—H17F109.5
C16A—C17A—H17A109.5H17D—C17B—H17F109.5
C16A—C17A—H17B109.5H17E—C17B—H17F109.5
H17A—C17A—H17B109.5C5B—C18B—C19B132.9 (2)
C16A—C17A—H17C109.5C5B—C18B—H18B113.5
H17A—C17A—H17C109.5C19B—C18B—H18B113.5
H17B—C17A—H17C109.5C24B—C19B—C20B116.0 (2)
C5A—C18A—C19A131.6 (3)C24B—C19B—C18B116.7 (2)
C5A—C18A—H18A114.2C20B—C19B—C18B127.2 (2)
C19A—C18A—H18A114.2C21B—C20B—C19B122.0 (2)
C24A—C19A—C20A116.0 (2)C21B—C20B—H20B119.0
C24A—C19A—C18A118.0 (2)C19B—C20B—H20B119.0
C20A—C19A—C18A126.0 (2)C20B—C21B—C22B121.7 (2)
C21A—C20A—C19A121.9 (3)C20B—C21B—H21B119.2
C21A—C20A—H20A119.1C22B—C21B—H21B119.2
C19A—C20A—H20A119.1N3B—C22B—C21B122.2 (2)
C20A—C21A—C22A121.7 (2)N3B—C22B—C23B121.0 (2)
C20A—C21A—H21A119.2C21B—C22B—C23B116.7 (2)
C22A—C21A—H21A119.2C24B—C23B—C22B120.4 (2)
N3A—C22A—C21A122.5 (2)C24B—C23B—H23B119.8
N3A—C22A—C23A120.8 (2)C22B—C23B—H23B119.8
C21A—C22A—C23A116.6 (2)C23B—C24B—C19B123.1 (2)
C24A—C23A—C22A120.8 (2)C23B—C24B—H24B118.4
C24A—C23A—H23A119.6C19B—C24B—H24B118.4
C22A—C23A—H23A119.6N3B—C25B—C26B114.5 (2)
C23A—C24A—C19A123.0 (2)N3B—C25B—H25C108.6
C23A—C24A—H24A118.5C26B—C25B—H25C108.6
C19A—C24A—H24A118.5N3B—C25B—H25D108.6
N3A—C25A—C26A113.3 (2)C26B—C25B—H25D108.6
N3A—C25A—H25A108.9H25C—C25B—H25D107.6
C26A—C25A—H25A108.9C25B—C26B—H26D109.5
N3A—C25A—H25B108.9C25B—C26B—H26E109.5
C26A—C25A—H25B108.9H26D—C26B—H26E109.5
H25A—C25A—H25B107.7C25B—C26B—H26F109.5
C25A—C26A—H26A109.5H26D—C26B—H26F109.5
C25A—C26A—H26B109.5H26E—C26B—H26F109.5
H26A—C26A—H26B109.5N3B—C27B—C28B112.6 (2)
C25A—C26A—H26C109.5N3B—C27B—H27C109.1
H26A—C26A—H26C109.5C28B—C27B—H27C109.1
H26B—C26A—H26C109.5N3B—C27B—H27D109.1
N3A—C27A—C28A113.7 (2)C28B—C27B—H27D109.1
N3A—C27A—H27A108.8H27C—C27B—H27D107.8
C28A—C27A—H27A108.8C27B—C28B—H28D109.5
N3A—C27A—H27B108.8C27B—C28B—H28E109.5
C28A—C27A—H27B108.8H28D—C28B—H28E109.5
H27A—C27A—H27B107.7C27B—C28B—H28F109.5
C27A—C28A—H28A109.5H28D—C28B—H28F109.5
C27A—C28A—H28B109.5H28E—C28B—H28F109.5
H28A—C28A—H28B109.5O3B—C29B—O2B123.6 (2)
C27A—C28A—H28C109.5O3B—C29B—C30B122.3 (2)
H28A—C28A—H28C109.5O2B—C29B—C30B114.1 (2)
H28B—C28A—H28C109.5C30Bii—C30B—C29B113.2 (3)
O3A—C29A—O2A123.1 (2)C30Bii—C30B—H30C108.9
O3A—C29A—C30A121.6 (2)C29B—C30B—H30C108.9
O2A—C29A—C30A115.3 (2)C30Bii—C30B—H30D108.9
C29A—C30A—C30Ai114.4 (3)C29B—C30B—H30D108.9
C29A—C30A—H30A108.7H30C—C30B—H30D107.7
C6A—N1A—C2A—C3A54.7 (3)C25A—N3A—C27A—C28A94.0 (3)
N1A—C2A—C3A—C7A148.4 (3)O3A—C29A—C30A—C30Ai10.3 (5)
N1A—C2A—C3A—C4A29.1 (3)O2A—C29A—C30A—C30Ai172.2 (3)
C7A—C3A—C4A—O1A8.5 (4)C6B—N1B—C2B—C3B59.1 (3)
C2A—C3A—C4A—O1A173.8 (2)N1B—C2B—C3B—C7B152.7 (2)
C7A—C3A—C4A—C5A170.4 (2)N1B—C2B—C3B—C4B22.9 (3)
C2A—C3A—C4A—C5A7.3 (4)C7B—C3B—C4B—O1B6.0 (4)
O1A—C4A—C5A—C18A12.0 (4)C2B—C3B—C4B—O1B169.9 (3)
C3A—C4A—C5A—C18A166.8 (2)C7B—C3B—C4B—C5B173.6 (2)
O1A—C4A—C5A—C6A171.2 (3)C2B—C3B—C4B—C5B10.5 (4)
C3A—C4A—C5A—C6A9.9 (4)O1B—C4B—C5B—C18B9.9 (4)
C2A—N1A—C6A—C5A57.4 (3)C3B—C4B—C5B—C18B169.7 (2)
C18A—C5A—C6A—N1A142.1 (3)O1B—C4B—C5B—C6B171.2 (3)
C4A—C5A—C6A—N1A34.3 (3)C3B—C4B—C5B—C6B9.2 (4)
C4A—C3A—C7A—C8A178.5 (3)C2B—N1B—C6B—C5B60.1 (3)
C2A—C3A—C7A—C8A3.9 (5)C18B—C5B—C6B—N1B156.1 (3)
C3A—C7A—C8A—C13A156.3 (3)C4B—C5B—C6B—N1B25.1 (3)
C3A—C7A—C8A—C9A27.0 (5)C4B—C3B—C7B—C8B173.8 (3)
C13A—C8A—C9A—C10A2.2 (5)C2B—C3B—C7B—C8B1.8 (5)
C7A—C8A—C9A—C10A179.0 (3)C3B—C7B—C8B—C13B156.7 (3)
C8A—C9A—C10A—C11A0.2 (6)C3B—C7B—C8B—C9B21.3 (5)
C16A—N2A—C11A—C12A5.1 (6)C13B—C8B—C9B—C10B3.2 (4)
C14C—N2A—C11A—C12A145.5 (4)C7B—C8B—C9B—C10B174.9 (3)
C14A—N2A—C11A—C12A166.9 (3)C8B—C9B—C10B—C11B1.8 (4)
C16A—N2A—C11A—C10A176.3 (4)C16B—N2B—C11B—C12B2.5 (4)
C14C—N2A—C11A—C10A35.9 (6)C14B—N2B—C11B—C12B169.5 (3)
C14A—N2A—C11A—C10A11.7 (6)C16B—N2B—C11B—C10B178.0 (3)
C9A—C10A—C11A—N2A177.3 (4)C14B—N2B—C11B—C10B11.1 (4)
C9A—C10A—C11A—C12A1.4 (5)C9B—C10B—C11B—N2B174.3 (3)
N2A—C11A—C12A—C13A177.9 (3)C9B—C10B—C11B—C12B5.2 (4)
C10A—C11A—C12A—C13A0.8 (5)N2B—C11B—C12B—C13B175.9 (3)
C11A—C12A—C13A—C8A1.3 (4)C10B—C11B—C12B—C13B3.6 (4)
C9A—C8A—C13A—C12A2.8 (4)C11B—C12B—C13B—C8B1.3 (4)
C7A—C8A—C13A—C12A179.9 (3)C9B—C8B—C13B—C12B4.7 (4)
C11A—N2A—C14A—C15A93.6 (5)C7B—C8B—C13B—C12B173.5 (3)
C16A—N2A—C14A—C15A94.1 (5)C11B—N2B—C14B—C15B88.1 (3)
C14C—N2A—C14A—C15A0.7 (5)C16B—N2B—C14B—C15B104.1 (3)
C11A—N2A—C14C—C15C104.9 (6)C11B—N2B—C16B—C17B82.7 (4)
C16A—N2A—C14C—C15C111.1 (6)C14B—N2B—C16B—C17B85.0 (3)
C14A—N2A—C14C—C15C6.1 (5)C4B—C5B—C18B—C19B173.2 (3)
C11A—N2A—C16A—C17A78.5 (4)C6B—C5B—C18B—C19B5.6 (5)
C14C—N2A—C16A—C17A62.9 (4)C5B—C18B—C19B—C24B177.8 (3)
C14A—N2A—C16A—C17A109.1 (4)C5B—C18B—C19B—C20B2.0 (5)
C4A—C5A—C18A—C19A179.8 (3)C24B—C19B—C20B—C21B0.3 (4)
C6A—C5A—C18A—C19A3.7 (5)C18B—C19B—C20B—C21B176.1 (3)
C5A—C18A—C19A—C24A159.5 (3)C19B—C20B—C21B—C22B2.9 (4)
C5A—C18A—C19A—C20A24.1 (5)C25B—N3B—C22B—C21B3.6 (4)
C24A—C19A—C20A—C21A0.5 (4)C27B—N3B—C22B—C21B177.9 (3)
C18A—C19A—C20A—C21A177.0 (3)C25B—N3B—C22B—C23B179.5 (3)
C19A—C20A—C21A—C22A0.4 (4)C27B—N3B—C22B—C23B0.9 (4)
C27A—N3A—C22A—C21A169.4 (2)C20B—C21B—C22B—N3B173.5 (3)
C25A—N3A—C22A—C21A4.4 (4)C20B—C21B—C22B—C23B3.6 (4)
C27A—N3A—C22A—C23A13.7 (4)N3B—C22B—C23B—C24B175.3 (3)
C25A—N3A—C22A—C23A172.5 (2)C21B—C22B—C23B—C24B1.8 (4)
C20A—C21A—C22A—N3A177.4 (3)C22B—C23B—C24B—C19B0.8 (4)
C20A—C21A—C22A—C23A0.4 (4)C20B—C19B—C24B—C23B1.5 (4)
N3A—C22A—C23A—C24A176.6 (2)C18B—C19B—C24B—C23B174.7 (3)
C21A—C22A—C23A—C24A0.5 (4)C22B—N3B—C25B—C26B80.6 (3)
C22A—C23A—C24A—C19A1.4 (4)C27B—N3B—C25B—C26B97.9 (3)
C20A—C19A—C24A—C23A1.4 (4)C22B—N3B—C27B—C28B81.2 (3)
C18A—C19A—C24A—C23A178.2 (2)C25B—N3B—C27B—C28B97.4 (3)
C22A—N3A—C25A—C26A85.9 (3)O3B—C29B—C30B—C30Bii4.1 (4)
C27A—N3A—C25A—C26A88.3 (3)O2B—C29B—C30B—C30Bii177.3 (3)
C22A—N3A—C27A—C28A91.8 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1B···O2A0.931.612.538 (3)173
N1B—H1C···O3Ai0.901.972.833 (3)161
N1B—H1D···O2B0.941.632.561 (3)174
Symmetry code: (i) x+1, y+1, z+1.
(III) Bis{(E,E)-3,5-bis[4-(diethylamino)benzylidene]-4-oxopiperidinium} decanedioate top
Crystal data top
2C27H36N3O+·C10H16O42Z = 1
Mr = 1037.40F(000) = 562
Triclinic, P1Dx = 1.209 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.2905 (8) ÅCell parameters from 1012 reflections
b = 12.7532 (13) Åθ = 2.4–20.3°
c = 14.0762 (14) ŵ = 0.08 mm1
α = 87.076 (2)°T = 100 K
β = 77.516 (2)°Plate, red
γ = 78.660 (2)°0.15 × 0.10 × 0.02 mm
V = 1424.7 (2) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer
7586 independent reflections
Radiation source: fine-focus sealed tube5558 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 29.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
h = 1111
Tmin = 0.989, Tmax = 0.998k = 1717
17369 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: difference Fourier map
wR(F2) = 0.118H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0554P)2 + 0.3P]
where P = (Fo2 + 2Fc2)/3
7586 reflections(Δ/σ)max = 0.001
355 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

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) top
xyzUiso*/Ueq
O10.59902 (14)0.60180 (8)0.89599 (7)0.0276 (2)
N10.69851 (13)0.51716 (8)0.61076 (7)0.0165 (2)
H1A0.58800.52010.61870.020*
H1B0.75080.49900.54630.020*
N20.56579 (15)1.17048 (9)0.57569 (9)0.0254 (3)
N30.85021 (14)0.06577 (9)0.87313 (8)0.0220 (2)
C20.72551 (16)0.62570 (10)0.62708 (9)0.0174 (2)
H2A0.66630.67760.58540.021*
H2B0.84720.62710.60750.021*
C30.66330 (15)0.65947 (10)0.73163 (9)0.0171 (2)
C40.65092 (16)0.57603 (10)0.81004 (9)0.0186 (3)
C50.70388 (15)0.46187 (10)0.78150 (9)0.0170 (2)
C60.77337 (16)0.43551 (10)0.67543 (8)0.0167 (2)
H6A0.89690.43050.66100.020*
H6B0.75030.36500.66220.020*
C70.61652 (15)0.76243 (10)0.76075 (9)0.0180 (3)
H70.57790.77020.82910.022*
C80.61377 (16)0.86319 (10)0.70808 (9)0.0182 (3)
C90.68919 (16)0.87855 (11)0.60996 (9)0.0201 (3)
H90.75130.81830.57250.024*
C100.67564 (17)0.97840 (11)0.56669 (10)0.0220 (3)
H100.72840.98510.50030.026*
C110.58503 (16)1.07112 (10)0.61879 (10)0.0207 (3)
C120.51516 (17)1.05680 (11)0.71839 (10)0.0215 (3)
H120.45701.11720.75690.026*
C130.53041 (16)0.95651 (11)0.76011 (9)0.0201 (3)
H130.48230.94990.82730.024*
C140.66240 (17)1.18755 (11)0.47834 (10)0.0243 (3)
H14A0.60921.25580.45170.029*
H14B0.65841.12930.43550.029*
C150.84530 (18)1.19104 (12)0.47672 (10)0.0266 (3)
H15A0.90431.20110.40960.040*
H15B0.89901.12370.50290.040*
H15C0.85051.25060.51660.040*
C160.46798 (18)1.26407 (11)0.63129 (11)0.0257 (3)
H16A0.49321.32960.59510.031*
H16B0.50301.26390.69420.031*
C170.27894 (18)1.26727 (12)0.65061 (11)0.0293 (3)
H17A0.22051.32570.69530.044*
H17B0.25451.19920.67980.044*
H17C0.24041.27900.58920.044*
C180.68463 (16)0.38801 (10)0.85356 (9)0.0181 (3)
H180.63090.41730.91570.022*
C190.73132 (16)0.27228 (10)0.85293 (9)0.0179 (2)
C200.84865 (16)0.21016 (11)0.77978 (9)0.0196 (3)
H200.90180.24520.72400.024*
C210.88917 (16)0.10029 (11)0.78628 (9)0.0202 (3)
H210.96910.06170.73510.024*
C220.81410 (16)0.04376 (10)0.86766 (9)0.0191 (3)
C230.70082 (17)0.10605 (11)0.94272 (9)0.0217 (3)
H230.65080.07150.99970.026*
C240.66114 (17)0.21572 (11)0.93520 (9)0.0211 (3)
H240.58380.25460.98720.025*
C250.96848 (17)0.12879 (11)0.79549 (10)0.0232 (3)
H25A0.95030.09670.73220.028*
H25B0.94370.20190.79860.028*
C261.15265 (18)0.13694 (12)0.79899 (11)0.0278 (3)
H26A1.22360.18200.74560.042*
H26B1.17250.16870.86130.042*
H26C1.18060.06540.79220.042*
C270.77194 (18)0.12394 (12)0.95737 (10)0.0253 (3)
H27A0.77200.19710.93710.030*
H27B0.65320.08790.97920.030*
C280.8590 (2)0.13158 (13)1.04257 (11)0.0317 (3)
H28A0.79740.16851.09710.048*
H28B0.86160.05951.06250.048*
H28C0.97440.17171.02310.048*
O20.63112 (12)0.44419 (8)0.40128 (7)0.0248 (2)
O30.86938 (11)0.47165 (8)0.43417 (6)0.0222 (2)
C290.78091 (16)0.45307 (10)0.37599 (9)0.0167 (2)
C300.87086 (16)0.43889 (11)0.26976 (9)0.0202 (3)
H30A0.93760.49600.25160.024*
H30B0.95080.36960.26330.024*
C310.75748 (18)0.44158 (13)0.19799 (10)0.0271 (3)
H31A0.68060.51200.20170.033*
H31B0.68780.38610.21670.033*
C320.8557 (2)0.42265 (14)0.09303 (10)0.0330 (4)
H32A0.93790.35450.09050.040*
H32B0.77640.41500.05150.040*
C330.9489 (2)0.51130 (13)0.05157 (10)0.0315 (3)
H33A1.02540.52090.09420.038*
H33B0.86660.57900.05140.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0430 (6)0.0222 (5)0.0141 (4)0.0019 (4)0.0022 (4)0.0021 (4)
N10.0179 (5)0.0208 (5)0.0115 (5)0.0050 (4)0.0033 (4)0.0008 (4)
N20.0244 (6)0.0212 (6)0.0258 (6)0.0029 (5)0.0027 (5)0.0041 (5)
N30.0253 (6)0.0196 (6)0.0197 (5)0.0042 (5)0.0015 (4)0.0009 (4)
C20.0199 (6)0.0186 (6)0.0142 (6)0.0054 (5)0.0032 (5)0.0002 (4)
C30.0168 (6)0.0214 (6)0.0142 (5)0.0054 (5)0.0040 (4)0.0008 (5)
C40.0211 (6)0.0209 (6)0.0143 (6)0.0043 (5)0.0045 (5)0.0004 (5)
C50.0170 (6)0.0209 (6)0.0137 (5)0.0038 (5)0.0038 (4)0.0013 (5)
C60.0189 (6)0.0177 (6)0.0137 (5)0.0038 (5)0.0033 (4)0.0001 (4)
C70.0176 (6)0.0224 (6)0.0150 (6)0.0050 (5)0.0041 (5)0.0003 (5)
C80.0181 (6)0.0201 (6)0.0175 (6)0.0056 (5)0.0045 (5)0.0007 (5)
C90.0202 (6)0.0204 (6)0.0192 (6)0.0046 (5)0.0017 (5)0.0028 (5)
C100.0239 (7)0.0234 (7)0.0184 (6)0.0070 (5)0.0014 (5)0.0012 (5)
C110.0191 (6)0.0197 (6)0.0234 (6)0.0052 (5)0.0037 (5)0.0019 (5)
C120.0227 (7)0.0192 (6)0.0217 (6)0.0036 (5)0.0030 (5)0.0021 (5)
C130.0207 (6)0.0239 (7)0.0165 (6)0.0067 (5)0.0033 (5)0.0002 (5)
C140.0262 (7)0.0241 (7)0.0217 (6)0.0066 (6)0.0029 (5)0.0055 (5)
C150.0266 (7)0.0277 (7)0.0246 (7)0.0089 (6)0.0000 (6)0.0012 (6)
C160.0283 (7)0.0175 (6)0.0302 (7)0.0051 (6)0.0035 (6)0.0011 (5)
C170.0274 (7)0.0255 (7)0.0314 (8)0.0009 (6)0.0030 (6)0.0023 (6)
C180.0190 (6)0.0211 (6)0.0137 (5)0.0028 (5)0.0030 (5)0.0017 (5)
C190.0191 (6)0.0208 (6)0.0142 (6)0.0045 (5)0.0040 (5)0.0002 (5)
C200.0201 (6)0.0237 (7)0.0146 (6)0.0047 (5)0.0027 (5)0.0026 (5)
C210.0213 (6)0.0233 (7)0.0146 (6)0.0026 (5)0.0015 (5)0.0020 (5)
C220.0190 (6)0.0206 (6)0.0185 (6)0.0038 (5)0.0052 (5)0.0009 (5)
C230.0230 (7)0.0233 (7)0.0172 (6)0.0051 (5)0.0013 (5)0.0028 (5)
C240.0214 (6)0.0241 (7)0.0151 (6)0.0015 (5)0.0006 (5)0.0011 (5)
C250.0250 (7)0.0210 (7)0.0233 (7)0.0043 (5)0.0032 (5)0.0056 (5)
C260.0254 (7)0.0317 (8)0.0255 (7)0.0044 (6)0.0038 (6)0.0034 (6)
C270.0260 (7)0.0230 (7)0.0279 (7)0.0077 (6)0.0053 (6)0.0012 (5)
C280.0332 (8)0.0343 (8)0.0269 (7)0.0035 (7)0.0073 (6)0.0004 (6)
O20.0187 (5)0.0358 (6)0.0197 (5)0.0066 (4)0.0026 (4)0.0009 (4)
O30.0218 (5)0.0319 (5)0.0142 (4)0.0082 (4)0.0033 (3)0.0022 (4)
C290.0191 (6)0.0156 (6)0.0149 (6)0.0026 (5)0.0035 (5)0.0007 (4)
C300.0206 (6)0.0260 (7)0.0146 (6)0.0057 (5)0.0035 (5)0.0026 (5)
C310.0254 (7)0.0434 (9)0.0163 (6)0.0139 (6)0.0059 (5)0.0002 (6)
C320.0401 (9)0.0482 (10)0.0166 (6)0.0218 (8)0.0067 (6)0.0007 (6)
C330.0404 (9)0.0392 (9)0.0174 (7)0.0148 (7)0.0052 (6)0.0018 (6)
Geometric parameters (Å, º) top
O1—C41.2317 (15)C17—H17A0.9800
N1—C61.4803 (15)C17—H17B0.9800
N1—C21.4818 (16)C17—H17C0.9800
N1—H1A0.8925C18—C191.4503 (18)
N1—H1B0.9360C18—H180.9500
N2—C111.3722 (17)C19—C201.4076 (18)
N2—C141.4596 (17)C19—C241.4101 (17)
N2—C161.4611 (18)C20—C211.3782 (19)
N3—C221.3717 (17)C20—H200.9500
N3—C251.4554 (17)C21—C221.4155 (18)
N3—C271.4643 (17)C21—H210.9500
C2—C31.5055 (17)C22—C231.4116 (18)
C2—H2A0.9900C23—C241.3764 (19)
C2—H2B0.9900C23—H230.9500
C3—C71.3522 (18)C24—H240.9500
C3—C41.4951 (17)C25—C261.521 (2)
C4—C51.4852 (18)C25—H25A0.9900
C5—C181.3540 (17)C25—H25B0.9900
C5—C61.5090 (16)C26—H26A0.9800
C6—H6A0.9900C26—H26B0.9800
C6—H6B0.9900C26—H26C0.9800
C7—C81.4492 (18)C27—C281.518 (2)
C7—H70.9500C27—H27A0.9900
C8—C131.4061 (18)C27—H27B0.9900
C8—C91.4086 (17)C28—H28A0.9800
C9—C101.3781 (19)C28—H28B0.9800
C9—H90.9500C28—H28C0.9800
C10—C111.4148 (19)O2—C291.2417 (15)
C10—H100.9500O3—C291.2699 (15)
C11—C121.4138 (18)C29—C301.5222 (17)
C12—C131.3742 (18)C30—C311.5165 (18)
C12—H120.9500C30—H30A0.9900
C13—H130.9500C30—H30B0.9900
C14—C151.5209 (19)C31—C321.5308 (19)
C14—H14A0.9900C31—H31A0.9900
C14—H14B0.9900C31—H31B0.9900
C15—H15A0.9800C32—C331.516 (2)
C15—H15B0.9800C32—H32A0.9900
C15—H15C0.9800C32—H32B0.9900
C16—C171.524 (2)C33—C33i1.524 (3)
C16—H16A0.9900C33—H33A0.9900
C16—H16B0.9900C33—H33B0.9900
C6—N1—C2112.61 (9)C16—C17—H17C109.5
C6—N1—H1A111.5H17A—C17—H17C109.5
C2—N1—H1A107.9H17B—C17—H17C109.5
C6—N1—H1B108.1C5—C18—C19131.59 (12)
C2—N1—H1B107.4C5—C18—H18114.2
H1A—N1—H1B109.2C19—C18—H18114.2
C11—N2—C14120.58 (12)C20—C19—C24116.00 (12)
C11—N2—C16120.59 (11)C20—C19—C18126.08 (11)
C14—N2—C16118.20 (11)C24—C19—C18117.82 (11)
C22—N3—C25121.25 (11)C21—C20—C19122.30 (12)
C22—N3—C27121.39 (11)C21—C20—H20118.9
C25—N3—C27117.35 (11)C19—C20—H20118.9
N1—C2—C3112.45 (10)C20—C21—C22121.36 (12)
N1—C2—H2A109.1C20—C21—H21119.3
C3—C2—H2A109.1C22—C21—H21119.3
N1—C2—H2B109.1N3—C22—C23121.94 (12)
C3—C2—H2B109.1N3—C22—C21121.58 (12)
H2A—C2—H2B107.8C23—C22—C21116.48 (12)
C7—C3—C4116.45 (11)C24—C23—C22121.52 (12)
C7—C3—C2124.10 (11)C24—C23—H23119.2
C4—C3—C2119.45 (11)C22—C23—H23119.2
O1—C4—C5121.16 (11)C23—C24—C19122.26 (12)
O1—C4—C3120.57 (12)C23—C24—H24118.9
C5—C4—C3118.28 (11)C19—C24—H24118.9
C18—C5—C4116.98 (11)N3—C25—C26114.53 (11)
C18—C5—C6124.38 (11)N3—C25—H25A108.6
C4—C5—C6118.64 (10)C26—C25—H25A108.6
N1—C6—C5111.91 (10)N3—C25—H25B108.6
N1—C6—H6A109.2C26—C25—H25B108.6
C5—C6—H6A109.2H25A—C25—H25B107.6
N1—C6—H6B109.2C25—C26—H26A109.5
C5—C6—H6B109.2C25—C26—H26B109.5
H6A—C6—H6B107.9H26A—C26—H26B109.5
C3—C7—C8132.57 (12)C25—C26—H26C109.5
C3—C7—H7113.7H26A—C26—H26C109.5
C8—C7—H7113.7H26B—C26—H26C109.5
C13—C8—C9115.80 (12)N3—C27—C28113.85 (12)
C13—C8—C7117.23 (11)N3—C27—H27A108.8
C9—C8—C7126.96 (12)C28—C27—H27A108.8
C10—C9—C8121.98 (12)N3—C27—H27B108.8
C10—C9—H9119.0C28—C27—H27B108.8
C8—C9—H9119.0H27A—C27—H27B107.7
C9—C10—C11121.59 (12)C27—C28—H28A109.5
C9—C10—H10119.2C27—C28—H28B109.5
C11—C10—H10119.2H28A—C28—H28B109.5
N2—C11—C12121.18 (12)C27—C28—H28C109.5
N2—C11—C10122.15 (12)H28A—C28—H28C109.5
C12—C11—C10116.67 (12)H28B—C28—H28C109.5
C13—C12—C11120.73 (12)O2—C29—O3124.11 (11)
C13—C12—H12119.6O2—C29—C30120.03 (11)
C11—C12—H12119.6O3—C29—C30115.84 (11)
C12—C13—C8123.12 (12)C31—C30—C29115.39 (11)
C12—C13—H13118.4C31—C30—H30A108.4
C8—C13—H13118.4C29—C30—H30A108.4
N2—C14—C15113.10 (12)C31—C30—H30B108.4
N2—C14—H14A109.0C29—C30—H30B108.4
C15—C14—H14A109.0H30A—C30—H30B107.5
N2—C14—H14B109.0C30—C31—C32112.84 (12)
C15—C14—H14B109.0C30—C31—H31A109.0
H14A—C14—H14B107.8C32—C31—H31A109.0
C14—C15—H15A109.5C30—C31—H31B109.0
C14—C15—H15B109.5C32—C31—H31B109.0
H15A—C15—H15B109.5H31A—C31—H31B107.8
C14—C15—H15C109.5C33—C32—C31113.78 (13)
H15A—C15—H15C109.5C33—C32—H32A108.8
H15B—C15—H15C109.5C31—C32—H32A108.8
N2—C16—C17112.81 (12)C33—C32—H32B108.8
N2—C16—H16A109.0C31—C32—H32B108.8
C17—C16—H16A109.0H32A—C32—H32B107.7
N2—C16—H16B109.0C32—C33—C33i112.81 (16)
C17—C16—H16B109.0C32—C33—H33A109.0
H16A—C16—H16B107.8C33i—C33—H33A109.0
C16—C17—H17A109.5C32—C33—H33B109.0
C16—C17—H17B109.5C33i—C33—H33B109.0
H17A—C17—H17B109.5H33A—C33—H33B107.8
C6—N1—C2—C354.87 (14)C11—N2—C14—C1575.53 (17)
N1—C2—C3—C7155.30 (12)C16—N2—C14—C1595.50 (15)
N1—C2—C3—C424.71 (16)C11—N2—C16—C1774.08 (17)
C7—C3—C4—O10.63 (19)C14—N2—C16—C17114.89 (14)
C2—C3—C4—O1179.38 (12)C4—C5—C18—C19175.77 (13)
C7—C3—C4—C5178.94 (11)C6—C5—C18—C194.8 (2)
C2—C3—C4—C51.05 (17)C5—C18—C19—C2017.9 (2)
O1—C4—C5—C183.15 (19)C5—C18—C19—C24165.99 (14)
C3—C4—C5—C18177.28 (11)C24—C19—C20—C211.97 (19)
O1—C4—C5—C6177.40 (12)C18—C19—C20—C21178.15 (13)
C3—C4—C5—C62.17 (17)C19—C20—C21—C220.0 (2)
C2—N1—C6—C558.13 (13)C25—N3—C22—C23179.44 (12)
C18—C5—C6—N1148.43 (12)C27—N3—C22—C230.3 (2)
C4—C5—C6—N130.98 (15)C25—N3—C22—C210.39 (19)
C4—C3—C7—C8178.66 (13)C27—N3—C22—C21179.85 (12)
C2—C3—C7—C81.3 (2)C20—C21—C22—N3178.01 (12)
C3—C7—C8—C13169.59 (13)C20—C21—C22—C232.15 (19)
C3—C7—C8—C911.9 (2)N3—C22—C23—C24177.85 (13)
C13—C8—C9—C102.74 (19)C21—C22—C23—C242.32 (19)
C7—C8—C9—C10178.72 (13)C22—C23—C24—C190.3 (2)
C8—C9—C10—C110.1 (2)C20—C19—C24—C231.80 (19)
C14—N2—C11—C12169.05 (12)C18—C19—C24—C23178.31 (12)
C16—N2—C11—C121.8 (2)C22—N3—C25—C2681.35 (16)
C14—N2—C11—C1010.6 (2)C27—N3—C25—C2698.42 (14)
C16—N2—C11—C10178.56 (13)C22—N3—C27—C2883.14 (16)
C9—C10—C11—N2177.74 (13)C25—N3—C27—C2896.63 (15)
C9—C10—C11—C122.6 (2)O2—C29—C30—C3114.50 (18)
N2—C11—C12—C13177.85 (13)O3—C29—C30—C31166.89 (12)
C10—C11—C12—C132.45 (19)C29—C30—C31—C32177.81 (12)
C11—C12—C13—C80.3 (2)C30—C31—C32—C3366.58 (18)
C9—C8—C13—C122.87 (19)C31—C32—C33—C33i177.82 (17)
C7—C8—C13—C12178.44 (12)
Symmetry code: (i) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2ii0.891.862.7207 (14)161
N1—H1B···O30.941.682.6122 (13)172
Symmetry code: (ii) x+1, y+1, z+1.
 

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