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The title compound, C26H40N4O4, displays approximate twofold symmetry. The four amide groups are arranged such that four intramolecular N—H...O hydrogen bonds are formed. The mol­ecules are linked into layers by bifurcated (C—H)2...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803011358/bt6284sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803011358/bt6284Isup2.hkl
Contains datablock I

CCDC reference: 217471

Key indicators

  • Single-crystal X-ray study
  • T = 143 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.104
  • Data-to-parameter ratio = 16.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_320 Alert C Check Hybridisation of C1 in Main Residue ? PLAT_320 Alert C Check Hybridisation of C6 in Main Residue ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

This structure determination forms part of a short series of structures of norbornadiene and quadricyclane tetra-amides. Introductory material was presented in the previous paper (Winkler et al., 2003). Here we present the structure of the title compound, (I), a tetrakis(secondary amide) derivative of quadricyclane.

The molecule (Fig. 1) possesses approximate twofold symmetry. Molecular dimensions, including those of the strained quadricyclane system (Table 1), may be considered normal. The four amide groups are arranged such that four intramolecular hydrogen bonds (Table 2) of the type N—H···O are formed, in the same pattern as reported in the previous paper.

The molecules are connected to form layers perpendicular to the yz plane by two bifurcated intermolecular hydrogen bond systems (C—H)2···O of graph set R21(7) (Fig. 2). One of the H···O interactions, H4···O3, is very short, with a normalized H···O distance of only 2.21 Å.

Experimental top

The title compound was prepared according to Winkler (2002) and recrystallized from a solution in dichloromethane/methanol by evaporation.

Refinement top

H atoms bonded to N atoms were refined freely. Methyl H atoms were located in difference syntheses, idealized (C—H 0.98 Å and H—C—H 109.5°) and refined on the basis of rigid groups allowed to rotate but not tip. H atoms were included using a riding model with fixed C—H bond lengths of 1.00 (methine) or 0.95 Å (aromatic); Uiso(H) values were fixed at 1.2Ueq of the parent atom.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecule of the title compound in the crystal. Ellipsoids represent 30% probability levels. H-atom radii are arbitrary. Hydrogen bonds are indicated by dashed lines.
[Figure 2] Fig. 2. Packing diagram of the title compound, viewed perpendicular to the yz plane·Isopropyl groups have been omitted for clarity, as have other H atoms not involved in hydrogen bonds. Intermolecular hydrogen bonds are shown as thick dashed lines and intramolecular hydrogen bonds have been omitted.
N,N',N'',N'''-3-isopropylidenetetracyclo[3.2.0.02,7.04,5]heptane- 1,5,6,7-tetracarboxamide top
Crystal data top
C26H40N4O4F(000) = 1024
Mr = 472.62Dx = 1.174 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.3354 (18) ÅCell parameters from 6314 reflections
b = 12.1987 (16) Åθ = 2.2–28.5°
c = 16.981 (2) ŵ = 0.08 mm1
β = 104.454 (4)°T = 143 K
V = 2674.9 (6) Å3Prism, yellow
Z = 40.42 × 0.17 × 0.16 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
4203 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.037
Graphite monochromatorθmax = 26.4°, θmin = 1.6°
Detector resolution: 8.192 pixels mm-1h = 1616
ω scansk = 1515
35207 measured reflectionsl = 2121
5478 independent reflections
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0509P)2 + 0.6537P]
where P = (Fo2 + 2Fc2)/3
5478 reflections(Δ/σ)max < 0.001
333 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C26H40N4O4V = 2674.9 (6) Å3
Mr = 472.62Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.3354 (18) ŵ = 0.08 mm1
b = 12.1987 (16) ÅT = 143 K
c = 16.981 (2) Å0.42 × 0.17 × 0.16 mm
β = 104.454 (4)°
Data collection top
Bruker SMART 1000 CCD
diffractometer
4203 reflections with I > 2σ(I)
35207 measured reflectionsRint = 0.037
5478 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.25 e Å3
5478 reflectionsΔρmin = 0.19 e Å3
333 parameters
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
O10.40156 (7)0.71048 (9)0.33737 (6)0.0340 (2)
O20.11914 (7)0.47992 (8)0.25825 (6)0.0306 (2)
O30.11756 (7)0.43277 (8)0.52907 (5)0.0283 (2)
O40.40345 (8)0.65406 (9)0.60557 (6)0.0370 (3)
N10.29696 (9)0.58874 (10)0.25556 (7)0.0293 (3)
H010.2397 (13)0.5487 (14)0.2502 (10)0.041 (4)*
N20.06824 (8)0.40171 (9)0.36231 (7)0.0252 (2)
H020.0734 (12)0.4042 (13)0.4150 (11)0.040 (5)*
N30.25291 (9)0.51234 (10)0.61771 (7)0.0305 (3)
H030.3059 (13)0.5612 (14)0.6196 (10)0.043 (5)*
N40.46474 (8)0.72064 (10)0.50320 (7)0.0279 (3)
H040.4506 (13)0.7248 (14)0.4494 (11)0.044 (5)*
C10.25436 (10)0.64815 (10)0.37850 (8)0.0247 (3)
C20.23236 (10)0.75299 (10)0.41968 (7)0.0232 (3)
H20.26980.82240.41390.028*
C30.12181 (10)0.75539 (10)0.42154 (7)0.0222 (3)
C40.10115 (10)0.63777 (10)0.43070 (7)0.0219 (3)
H40.03100.61230.43400.026*
C50.16563 (10)0.56943 (11)0.38656 (8)0.0243 (3)
C60.19863 (10)0.58233 (11)0.48110 (8)0.0246 (3)
C70.28756 (10)0.66050 (11)0.47355 (8)0.0253 (3)
C80.05700 (10)0.84005 (11)0.41577 (8)0.0250 (3)
C90.05506 (11)0.82621 (12)0.41536 (9)0.0306 (3)
H9A0.07000.74830.42060.037*
H9B0.09860.85450.36420.037*
H9C0.06960.86680.46110.037*
C100.09022 (12)0.95642 (11)0.40749 (9)0.0331 (3)
H10A0.16380.95780.40770.040*
H10B0.07941.00000.45310.040*
H10C0.04920.98730.35630.040*
C110.32395 (10)0.65085 (11)0.32153 (8)0.0245 (3)
C120.35941 (11)0.57854 (13)0.19609 (8)0.0340 (3)
H120.41000.64050.20410.041*
C130.28954 (14)0.58536 (16)0.11088 (9)0.0470 (4)
H13A0.23850.52590.10280.056*
H13B0.33130.57850.07110.056*
H13C0.25360.65610.10360.056*
C140.41852 (15)0.47190 (18)0.20974 (11)0.0578 (5)
H14A0.46320.47030.26510.069*
H14B0.46110.46550.17060.069*
H14C0.36960.41060.20240.069*
C150.11694 (9)0.47874 (10)0.33112 (8)0.0231 (3)
C160.01322 (10)0.31093 (11)0.31338 (8)0.0261 (3)
H160.02480.34050.25920.031*
C170.06524 (12)0.26435 (13)0.35519 (10)0.0371 (4)
H17A0.02940.23730.40920.045*
H17B0.10260.20380.32270.045*
H17C0.11440.32180.36070.045*
C180.08837 (12)0.22424 (12)0.29976 (11)0.0393 (4)
H18A0.13920.25770.27420.047*
H18B0.05030.16680.26410.047*
H18C0.12420.19200.35210.047*
C190.18784 (10)0.50196 (11)0.54487 (8)0.0240 (3)
C200.24770 (11)0.44230 (13)0.68687 (8)0.0347 (3)
H200.17420.41830.67960.042*
C210.27845 (15)0.51000 (17)0.76390 (10)0.0526 (5)
H21A0.34850.53910.76990.063*
H21B0.27710.46380.81090.063*
H21C0.22970.57090.76070.063*
C220.31397 (14)0.34113 (15)0.68934 (11)0.0479 (4)
H22A0.28920.29930.63890.057*
H22B0.30950.29550.73590.057*
H22C0.38610.36300.69480.057*
C230.39074 (10)0.67671 (11)0.53276 (8)0.0258 (3)
C240.56923 (10)0.73967 (13)0.55390 (9)0.0333 (3)
H240.56420.76140.60960.040*
C250.61711 (13)0.83351 (15)0.51756 (11)0.0489 (4)
H25A0.61900.81490.46180.059*
H25B0.68770.84650.55040.059*
H25C0.57550.89990.51700.059*
C260.63320 (13)0.63621 (16)0.56064 (13)0.0581 (5)
H26A0.59980.57770.58440.070*
H26B0.70260.64990.59550.070*
H26C0.63870.61400.50640.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0344 (5)0.0450 (6)0.0251 (5)0.0151 (5)0.0120 (4)0.0058 (4)
O20.0344 (5)0.0320 (5)0.0261 (5)0.0097 (4)0.0088 (4)0.0027 (4)
O30.0302 (5)0.0299 (5)0.0257 (5)0.0036 (4)0.0086 (4)0.0055 (4)
O40.0338 (5)0.0468 (6)0.0282 (5)0.0094 (5)0.0038 (4)0.0061 (5)
N10.0283 (6)0.0334 (7)0.0296 (6)0.0085 (5)0.0134 (5)0.0064 (5)
N20.0282 (6)0.0256 (6)0.0220 (6)0.0060 (5)0.0069 (5)0.0036 (5)
N30.0297 (6)0.0345 (7)0.0272 (6)0.0055 (5)0.0071 (5)0.0076 (5)
N40.0239 (6)0.0356 (7)0.0225 (6)0.0055 (5)0.0024 (5)0.0001 (5)
C10.0285 (7)0.0217 (7)0.0261 (7)0.0020 (5)0.0105 (5)0.0008 (5)
C20.0288 (7)0.0204 (6)0.0202 (6)0.0028 (5)0.0059 (5)0.0006 (5)
C30.0281 (6)0.0217 (7)0.0167 (6)0.0016 (5)0.0054 (5)0.0006 (5)
C40.0236 (6)0.0221 (6)0.0204 (6)0.0006 (5)0.0060 (5)0.0008 (5)
C50.0235 (6)0.0235 (7)0.0274 (7)0.0008 (5)0.0088 (5)0.0024 (5)
C60.0236 (6)0.0253 (7)0.0254 (7)0.0016 (5)0.0073 (5)0.0049 (5)
C70.0253 (7)0.0229 (7)0.0271 (7)0.0014 (5)0.0055 (5)0.0031 (5)
C80.0338 (7)0.0226 (7)0.0180 (6)0.0024 (5)0.0054 (5)0.0013 (5)
C90.0338 (7)0.0275 (7)0.0311 (7)0.0084 (6)0.0094 (6)0.0014 (6)
C100.0429 (8)0.0213 (7)0.0333 (8)0.0030 (6)0.0063 (6)0.0013 (6)
C110.0271 (7)0.0242 (7)0.0233 (7)0.0006 (5)0.0085 (5)0.0034 (5)
C120.0336 (7)0.0427 (9)0.0299 (7)0.0099 (6)0.0157 (6)0.0081 (7)
C130.0538 (10)0.0597 (11)0.0305 (8)0.0054 (8)0.0164 (7)0.0060 (8)
C140.0526 (10)0.0841 (15)0.0399 (10)0.0276 (10)0.0176 (8)0.0008 (9)
C150.0212 (6)0.0220 (7)0.0261 (7)0.0016 (5)0.0062 (5)0.0021 (5)
C160.0288 (7)0.0230 (7)0.0253 (7)0.0047 (5)0.0046 (5)0.0012 (5)
C170.0357 (8)0.0370 (8)0.0408 (9)0.0128 (6)0.0135 (7)0.0055 (7)
C180.0421 (9)0.0256 (8)0.0533 (10)0.0034 (6)0.0178 (7)0.0060 (7)
C190.0232 (6)0.0249 (7)0.0261 (7)0.0046 (5)0.0101 (5)0.0042 (5)
C200.0334 (7)0.0456 (9)0.0252 (7)0.0046 (7)0.0075 (6)0.0113 (6)
C210.0587 (11)0.0705 (13)0.0286 (8)0.0065 (9)0.0110 (8)0.0026 (8)
C220.0521 (10)0.0500 (10)0.0423 (9)0.0062 (8)0.0130 (8)0.0203 (8)
C230.0268 (7)0.0225 (7)0.0273 (7)0.0002 (5)0.0051 (5)0.0012 (5)
C240.0238 (7)0.0445 (9)0.0294 (7)0.0061 (6)0.0025 (6)0.0015 (6)
C250.0374 (9)0.0568 (11)0.0493 (10)0.0189 (8)0.0045 (7)0.0029 (8)
C260.0333 (9)0.0588 (12)0.0777 (14)0.0079 (8)0.0053 (9)0.0096 (10)
Geometric parameters (Å, º) top
O1—C111.2384 (16)C10—H10B0.9800
O2—C151.2451 (16)C10—H10C0.9800
O3—C191.2398 (16)C12—C141.509 (2)
O4—C231.2364 (16)C12—C131.515 (2)
N1—C111.3256 (17)C12—H121.0000
N1—C121.4659 (17)C13—H13A0.9800
N1—H010.892 (17)C13—H13B0.9800
N2—C151.3255 (17)C13—H13C0.9800
N2—C161.4666 (17)C14—H14A0.9800
N2—H020.881 (17)C14—H14B0.9800
N3—C191.3278 (17)C14—H14C0.9800
N3—C201.4679 (18)C16—C181.514 (2)
N3—H030.919 (18)C16—C171.5141 (19)
N4—C231.3268 (17)C16—H161.0000
N4—C241.4622 (17)C17—H17A0.9800
N4—H040.888 (18)C17—H17B0.9800
C1—C111.4988 (18)C17—H17C0.9800
C1—C21.5209 (18)C18—H18A0.9800
C1—C51.5563 (17)C18—H18B0.9800
C1—C71.5707 (18)C18—H18C0.9800
C2—C31.4828 (18)C20—C221.512 (2)
C2—C71.5217 (18)C20—C211.514 (2)
C2—H21.0000C20—H201.0000
C3—C81.3345 (18)C21—H21A0.9800
C3—C41.4765 (18)C21—H21B0.9800
C4—C51.5224 (17)C21—H21C0.9800
C4—C61.5245 (17)C22—H22A0.9800
C4—H41.0000C22—H22B0.9800
C5—C151.4922 (18)C22—H22C0.9800
C5—C61.5630 (18)C24—C261.512 (2)
C6—C191.4941 (18)C24—C251.515 (2)
C6—C71.5517 (17)C24—H241.0000
C7—C231.5009 (18)C25—H25A0.9800
C8—C91.5021 (19)C25—H25B0.9800
C8—C101.5041 (19)C25—H25C0.9800
C9—H9A0.9800C26—H26A0.9800
C9—H9B0.9800C26—H26B0.9800
C9—H9C0.9800C26—H26C0.9800
C10—H10A0.9800
C11—N1—C12123.34 (12)C12—C13—H13A109.5
C11—N1—H01116.4 (11)C12—C13—H13B109.5
C12—N1—H01120.1 (11)H13A—C13—H13B109.5
C15—N2—C16122.32 (11)C12—C13—H13C109.5
C15—N2—H02117.4 (11)H13A—C13—H13C109.5
C16—N2—H02120.2 (11)H13B—C13—H13C109.5
C19—N3—C20122.64 (12)C12—C14—H14A109.5
C19—N3—H03114.4 (10)C12—C14—H14B109.5
C20—N3—H03122.6 (10)H14A—C14—H14B109.5
C23—N4—C24122.06 (12)C12—C14—H14C109.5
C23—N4—H04115.2 (11)H14A—C14—H14C109.5
C24—N4—H04121.6 (11)H14B—C14—H14C109.5
C11—C1—C2119.99 (11)O2—C15—N2122.73 (12)
C11—C1—C5132.62 (11)O2—C15—C5120.26 (12)
C2—C1—C5103.91 (10)N2—C15—C5116.93 (11)
C11—C1—C7126.88 (11)N2—C16—C18110.94 (11)
C2—C1—C758.95 (8)N2—C16—C17108.92 (11)
C5—C1—C789.67 (9)C18—C16—C17111.76 (12)
C3—C2—C1109.47 (10)N2—C16—H16108.4
C3—C2—C7109.64 (10)C18—C16—H16108.4
C1—C2—C762.16 (9)C17—C16—H16108.4
C3—C2—H2120.6C16—C17—H17A109.5
C1—C2—H2120.6C16—C17—H17B109.5
C7—C2—H2120.6H17A—C17—H17B109.5
C8—C3—C4128.71 (12)C16—C17—H17C109.5
C8—C3—C2130.00 (12)H17A—C17—H17C109.5
C4—C3—C2101.29 (10)H17B—C17—H17C109.5
C3—C4—C5109.70 (10)C16—C18—H18A109.5
C3—C4—C6109.56 (10)C16—C18—H18B109.5
C5—C4—C661.73 (8)H18A—C18—H18B109.5
C3—C4—H4120.6C16—C18—H18C109.5
C5—C4—H4120.6H18A—C18—H18C109.5
C6—C4—H4120.6H18B—C18—H18C109.5
C15—C5—C4120.42 (11)O3—C19—N3123.33 (12)
C15—C5—C1128.51 (11)O3—C19—C6119.62 (11)
C4—C5—C1103.92 (10)N3—C19—C6116.99 (12)
C15—C5—C6133.58 (11)N3—C20—C22110.68 (12)
C4—C5—C659.20 (8)N3—C20—C21108.47 (13)
C1—C5—C690.16 (9)C22—C20—C21113.00 (14)
C19—C6—C4118.36 (10)N3—C20—H20108.2
C19—C6—C7132.61 (11)C22—C20—H20108.2
C4—C6—C7104.07 (10)C21—C20—H20108.2
C19—C6—C5128.68 (11)C20—C21—H21A109.5
C4—C6—C559.07 (8)C20—C21—H21B109.5
C7—C6—C590.12 (9)H21A—C21—H21B109.5
C23—C7—C2122.01 (11)C20—C21—H21C109.5
C23—C7—C6128.12 (11)H21A—C21—H21C109.5
C2—C7—C6103.91 (10)H21B—C21—H21C109.5
C23—C7—C1132.62 (11)C20—C22—H22A109.5
C2—C7—C158.89 (8)C20—C22—H22B109.5
C6—C7—C190.05 (9)H22A—C22—H22B109.5
C3—C8—C9122.59 (12)C20—C22—H22C109.5
C3—C8—C10122.46 (12)H22A—C22—H22C109.5
C9—C8—C10114.93 (12)H22B—C22—H22C109.5
C8—C9—H9A109.5O4—C23—N4122.64 (12)
C8—C9—H9B109.5O4—C23—C7120.95 (12)
H9A—C9—H9B109.5N4—C23—C7116.35 (12)
C8—C9—H9C109.5N4—C24—C26110.42 (13)
H9A—C9—H9C109.5N4—C24—C25108.46 (12)
H9B—C9—H9C109.5C26—C24—C25111.98 (14)
C8—C10—H10A109.5N4—C24—H24108.6
C8—C10—H10B109.5C26—C24—H24108.6
H10A—C10—H10B109.5C25—C24—H24108.6
C8—C10—H10C109.5C24—C25—H25A109.5
H10A—C10—H10C109.5C24—C25—H25B109.5
H10B—C10—H10C109.5H25A—C25—H25B109.5
O1—C11—N1123.72 (12)C24—C25—H25C109.5
O1—C11—C1119.42 (12)H25A—C25—H25C109.5
N1—C11—C1116.85 (11)H25B—C25—H25C109.5
N1—C12—C14109.40 (13)C24—C26—H26A109.5
N1—C12—C13109.48 (12)C24—C26—H26B109.5
C14—C12—C13111.55 (14)H26A—C26—H26B109.5
N1—C12—H12108.8C24—C26—H26C109.5
C14—C12—H12108.8H26A—C26—H26C109.5
C13—C12—H12108.8H26B—C26—H26C109.5
C11—C1—C2—C3140.03 (12)C5—C6—C7—C10.22 (9)
C5—C1—C2—C321.47 (13)C11—C1—C7—C230.5 (2)
C7—C1—C2—C3102.50 (11)C2—C1—C7—C23106.62 (16)
C11—C1—C2—C7117.47 (13)C5—C1—C7—C23146.88 (14)
C5—C1—C2—C781.03 (10)C11—C1—C7—C2106.12 (14)
C1—C2—C3—C8145.96 (13)C5—C1—C7—C2106.50 (10)
C7—C2—C3—C8147.60 (13)C11—C1—C7—C6147.60 (13)
C1—C2—C3—C433.44 (13)C2—C1—C7—C6106.27 (10)
C7—C2—C3—C432.99 (13)C5—C1—C7—C60.22 (9)
C8—C3—C4—C5146.38 (13)C4—C3—C8—C91.9 (2)
C2—C3—C4—C533.03 (13)C2—C3—C8—C9177.32 (12)
C8—C3—C4—C6147.62 (13)C4—C3—C8—C10179.33 (12)
C2—C3—C4—C632.97 (13)C2—C3—C8—C101.4 (2)
C3—C4—C5—C15132.31 (12)C12—N1—C11—O13.8 (2)
C6—C4—C5—C15125.49 (13)C12—N1—C11—C1177.04 (12)
C3—C4—C5—C120.49 (13)C2—C1—C11—O138.23 (18)
C6—C4—C5—C181.70 (10)C5—C1—C11—O1166.51 (13)
C3—C4—C5—C6102.19 (11)C7—C1—C11—O133.62 (19)
C11—C1—C5—C157.7 (2)C2—C1—C11—N1141.00 (13)
C2—C1—C5—C15150.40 (12)C5—C1—C11—N114.3 (2)
C7—C1—C5—C15151.80 (13)C7—C1—C11—N1147.16 (13)
C11—C1—C5—C4157.44 (13)C11—N1—C12—C14101.65 (16)
C2—C1—C5—C40.63 (13)C11—N1—C12—C13135.82 (15)
C7—C1—C5—C458.43 (11)C16—N2—C15—O20.33 (19)
C11—C1—C5—C6144.35 (14)C16—N2—C15—C5177.17 (11)
C2—C1—C5—C657.58 (11)C4—C5—C15—O2121.03 (13)
C7—C1—C5—C60.22 (9)C1—C5—C15—O224.4 (2)
C3—C4—C6—C19137.28 (12)C6—C5—C15—O2164.08 (13)
C5—C4—C6—C19120.30 (13)C4—C5—C15—N255.89 (17)
C3—C4—C6—C720.92 (13)C1—C5—C15—N2158.64 (12)
C5—C4—C6—C781.51 (10)C6—C5—C15—N219.0 (2)
C3—C4—C6—C5102.42 (11)C15—N2—C16—C1877.86 (16)
C15—C5—C6—C191.0 (2)C15—N2—C16—C17158.72 (12)
C4—C5—C6—C19103.28 (14)C20—N3—C19—O30.0 (2)
C1—C5—C6—C19150.55 (13)C20—N3—C19—C6177.04 (12)
C15—C5—C6—C4104.27 (15)C4—C6—C19—O344.37 (17)
C1—C5—C6—C4106.17 (10)C7—C6—C19—O3164.94 (13)
C15—C5—C6—C7149.33 (14)C5—C6—C19—O327.21 (19)
C4—C5—C6—C7106.39 (10)C4—C6—C19—N3132.78 (13)
C1—C5—C6—C70.22 (9)C7—C6—C19—N317.9 (2)
C3—C2—C7—C23134.03 (12)C5—C6—C19—N3155.65 (12)
C1—C2—C7—C23123.74 (14)C19—N3—C20—C2289.94 (16)
C3—C2—C7—C620.76 (13)C19—N3—C20—C21145.56 (14)
C1—C2—C7—C681.46 (10)C24—N4—C23—O43.7 (2)
C3—C2—C7—C1102.22 (11)C24—N4—C23—C7179.21 (12)
C19—C6—C7—C230.9 (2)C2—C7—C23—O4125.20 (14)
C4—C6—C7—C23152.71 (13)C6—C7—C23—O423.1 (2)
C5—C6—C7—C23149.25 (13)C1—C7—C23—O4159.44 (13)
C19—C6—C7—C2153.60 (13)C2—C7—C23—N451.96 (18)
C4—C6—C7—C20.04 (13)C6—C7—C23—N4159.75 (13)
C5—C6—C7—C258.08 (11)C1—C7—C23—N423.4 (2)
C19—C6—C7—C1148.55 (14)C23—N4—C24—C2683.35 (18)
C4—C6—C7—C157.81 (11)C23—N4—C24—C25153.60 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H01···O20.892 (17)1.849 (18)2.7279 (15)168.3 (16)
N2—H02···O30.881 (17)1.910 (17)2.7686 (15)164.3 (15)
N3—H03···O40.919 (18)1.785 (18)2.6959 (16)170.6 (15)
N4—H04···O10.888 (18)1.858 (18)2.7331 (16)168.1 (16)
C9—H9B···O2i0.982.543.4176 (17)149
C10—H10C···O2i0.982.583.4461 (18)148
C4—H4···O3ii1.002.293.2723 (16)167
C9—H9A···O3ii0.982.513.4581 (17)164
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC26H40N4O4
Mr472.62
Crystal system, space groupMonoclinic, P21/c
Temperature (K)143
a, b, c (Å)13.3354 (18), 12.1987 (16), 16.981 (2)
β (°) 104.454 (4)
V3)2674.9 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.42 × 0.17 × 0.16
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
35207, 5478, 4203
Rint0.037
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.104, 1.04
No. of reflections5478
No. of parameters333
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.19

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), SHELXL97.

Selected geometric parameters (Å, º) top
C1—C21.5209 (18)C3—C81.3345 (18)
C1—C51.5563 (17)C3—C41.4765 (18)
C1—C71.5707 (18)C4—C51.5224 (17)
C2—C31.4828 (18)C4—C61.5245 (17)
C2—C71.5217 (18)C5—C61.5630 (18)
C11—C1—C2119.99 (11)C4—C5—C1103.92 (10)
C11—C1—C5132.62 (11)C15—C5—C6133.58 (11)
C2—C1—C5103.91 (10)C4—C5—C659.20 (8)
C11—C1—C7126.88 (11)C1—C5—C690.16 (9)
C2—C1—C758.95 (8)C19—C6—C4118.36 (10)
C5—C1—C789.67 (9)C19—C6—C7132.61 (11)
C3—C2—C1109.47 (10)C4—C6—C7104.07 (10)
C3—C2—C7109.64 (10)C19—C6—C5128.68 (11)
C1—C2—C762.16 (9)C4—C6—C559.07 (8)
C8—C3—C4128.71 (12)C7—C6—C590.12 (9)
C8—C3—C2130.00 (12)C23—C7—C2122.01 (11)
C4—C3—C2101.29 (10)C23—C7—C6128.12 (11)
C3—C4—C5109.70 (10)C2—C7—C6103.91 (10)
C3—C4—C6109.56 (10)C23—C7—C1132.62 (11)
C5—C4—C661.73 (8)C2—C7—C158.89 (8)
C15—C5—C4120.42 (11)C6—C7—C190.05 (9)
C15—C5—C1128.51 (11)
C2—C1—C11—O138.23 (18)C4—C6—C19—O344.37 (17)
C5—C1—C11—O1166.51 (13)C7—C6—C19—O3164.94 (13)
C7—C1—C11—O133.62 (19)C5—C6—C19—O327.21 (19)
C2—C1—C11—N1141.00 (13)C4—C6—C19—N3132.78 (13)
C5—C1—C11—N114.3 (2)C7—C6—C19—N317.9 (2)
C7—C1—C11—N1147.16 (13)C5—C6—C19—N3155.65 (12)
C4—C5—C15—O2121.03 (13)C2—C7—C23—O4125.20 (14)
C1—C5—C15—O224.4 (2)C6—C7—C23—O423.1 (2)
C6—C5—C15—O2164.08 (13)C1—C7—C23—O4159.44 (13)
C4—C5—C15—N255.89 (17)C2—C7—C23—N451.96 (18)
C1—C5—C15—N2158.64 (12)C6—C7—C23—N4159.75 (13)
C6—C5—C15—N219.0 (2)C1—C7—C23—N423.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H01···O20.892 (17)1.849 (18)2.7279 (15)168.3 (16)
N2—H02···O30.881 (17)1.910 (17)2.7686 (15)164.3 (15)
N3—H03···O40.919 (18)1.785 (18)2.6959 (16)170.6 (15)
N4—H04···O10.888 (18)1.858 (18)2.7331 (16)168.1 (16)
C9—H9B···O2i0.982.543.4176 (17)149
C10—H10C···O2i0.982.583.4461 (18)148
C4—H4···O3ii1.002.293.2723 (16)167
C9—H9A···O3ii0.982.513.4581 (17)164
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x, y+1, z+1.
 

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