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The molecule of the title compound, C38H56N4O4, 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 dimers by bifurcated (C—H)2...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013692/bt6289sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013692/bt6289Isup2.hkl
Contains datablock I

CCDC reference: 221671

Key indicators

  • Single-crystal X-ray study
  • T = 143 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.105
  • Data-to-parameter ratio = 16.4

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 . ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

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.

3-isopropylidenetetracyclo[3.2.0.02,7.04,5]heptane- 1,5,6,7-tetracarboxylic acid tetrakis(cyclohexylamide) top
Crystal data top
C38H56N4O4Z = 2
Mr = 632.87F(000) = 688
Triclinic, P1Dx = 1.208 Mg m3
a = 10.1995 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.6467 (16) ÅCell parameters from 6008 reflections
c = 15.206 (2) Åθ = 2–28°
α = 87.126 (3)°µ = 0.08 mm1
β = 77.132 (3)°T = 143 K
γ = 81.300 (3)°Tablet, colourless
V = 1740.5 (4) Å30.38 × 0.33 × 0.19 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
5126 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
Graphite monochromatorθmax = 26.4°, θmin = 1.4°
Detector resolution: 8.192 pixels mm-1h = 1212
ω scansk = 1414
15921 measured reflectionsl = 1919
7098 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0516P)2 + 0.1495P]
where P = (Fo2 + 2Fc2)/3
7098 reflections(Δ/σ)max = 0.001
433 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

Experimental. 3-Isopropylidene-tetracyclo[3.2.0.02,7.04,5]heptane- 1,5,6,7-tetracarboxylic acid tetrakis(cyclohexylamide)

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
O10.15459 (11)0.39917 (8)0.16088 (7)0.0287 (2)
O20.34661 (11)0.20025 (8)0.38288 (7)0.0292 (2)
O30.61172 (10)0.49388 (8)0.38177 (6)0.0249 (2)
O40.42131 (10)0.68948 (9)0.15772 (7)0.0290 (2)
N10.22496 (12)0.24171 (10)0.24092 (8)0.0237 (3)
H010.2594 (18)0.2184 (15)0.2895 (12)0.041 (5)*
N20.51995 (12)0.27909 (11)0.41313 (8)0.0254 (3)
H020.5586 (17)0.3438 (16)0.4091 (11)0.038 (5)*
N30.59840 (12)0.62321 (11)0.26646 (8)0.0251 (3)
H030.5415 (17)0.6567 (14)0.2296 (11)0.034 (4)*
N40.28627 (12)0.58752 (10)0.10339 (7)0.0225 (3)
H040.2337 (19)0.5252 (16)0.1158 (12)0.047 (5)*
C10.25948 (13)0.42979 (12)0.28042 (9)0.0203 (3)
C20.17811 (14)0.54797 (11)0.30926 (9)0.0198 (3)
H20.09870.58020.28270.024*
C30.17503 (13)0.56681 (11)0.40519 (9)0.0189 (3)
C40.30991 (13)0.50526 (11)0.41309 (9)0.0191 (3)
H40.33940.50260.47170.023*
C50.35107 (14)0.40152 (11)0.35031 (9)0.0199 (3)
C60.41198 (13)0.51615 (12)0.32369 (8)0.0203 (3)
C70.32190 (14)0.54361 (12)0.25335 (9)0.0204 (3)
C80.07612 (14)0.62359 (11)0.46717 (9)0.0212 (3)
C90.08406 (15)0.63024 (13)0.56416 (9)0.0258 (3)
H9A0.17230.59030.57240.031*
H9B0.01130.59290.60260.031*
H9C0.07380.71180.58080.031*
C100.05349 (15)0.68437 (13)0.44507 (10)0.0295 (3)
H10A0.04580.68430.37970.035*
H10B0.07010.76470.46580.035*
H10C0.12920.64380.47530.035*
C110.20902 (13)0.35430 (12)0.22199 (9)0.0200 (3)
C120.18365 (14)0.15460 (12)0.19075 (9)0.0239 (3)
H120.16400.19120.13330.029*
C130.30049 (16)0.05515 (13)0.16765 (11)0.0333 (4)
H13A0.32890.02520.22360.040*
H13B0.37890.08460.12720.040*
C140.26051 (17)0.04366 (14)0.12184 (12)0.0378 (4)
H14A0.24350.01640.06210.045*
H14B0.33650.10880.11210.045*
C150.13397 (18)0.08646 (13)0.17825 (11)0.0374 (4)
H15A0.10800.14770.14540.045*
H15B0.15340.12070.23570.045*
C160.01751 (17)0.01281 (14)0.19792 (11)0.0356 (4)
H16A0.06280.01590.23680.043*
H16B0.00720.04230.14070.043*
C170.05586 (16)0.11165 (13)0.24489 (10)0.0306 (3)
H17A0.02010.17680.25360.037*
H17B0.07050.08430.30510.037*
C180.40760 (14)0.28438 (12)0.38233 (8)0.0199 (3)
C190.57800 (14)0.17537 (12)0.45736 (9)0.0222 (3)
H190.50690.12310.47560.027*
C200.70010 (16)0.10923 (13)0.39436 (10)0.0295 (3)
H20A0.76750.16230.37070.035*
H20B0.67070.08110.34250.035*
C210.76632 (17)0.00616 (14)0.44261 (10)0.0342 (4)
H21A0.70330.05220.45830.041*
H21B0.84970.03050.40130.041*
C220.80250 (17)0.04123 (15)0.52738 (12)0.0401 (4)
H22A0.87480.09140.51120.048*
H22B0.83830.02900.55890.048*
C230.68006 (19)0.10589 (14)0.58981 (11)0.0390 (4)
H23A0.70790.13220.64290.047*
H23B0.61180.05290.61140.047*
C240.61671 (17)0.21061 (13)0.54174 (9)0.0293 (3)
H24A0.53470.24940.58320.035*
H24B0.68210.26690.52520.035*
C250.55041 (13)0.54306 (12)0.32541 (9)0.0199 (3)
C260.73020 (15)0.66198 (14)0.26104 (10)0.0312 (4)
H260.77040.62420.31140.037*
C270.71256 (19)0.79387 (16)0.27086 (12)0.0451 (4)
H27A0.64440.81650.32680.054*
H27B0.79990.81690.27640.054*
C280.6670 (2)0.85841 (16)0.19085 (16)0.0580 (6)
H28A0.66440.94290.19740.070*
H28B0.57410.84410.19010.070*
C290.7632 (2)0.81915 (19)0.10185 (14)0.0592 (6)
H29A0.72680.85750.05090.071*
H29B0.85300.84320.09910.071*
C300.77975 (18)0.68988 (18)0.09251 (11)0.0465 (5)
H30A0.84680.66670.03620.056*
H30B0.69190.66670.08830.056*
C310.82703 (16)0.62738 (16)0.17207 (11)0.0387 (4)
H31A0.91840.64560.17320.046*
H31B0.83460.54250.16470.046*
C320.34906 (14)0.61144 (12)0.16647 (9)0.0209 (3)
C330.28573 (14)0.65902 (12)0.02159 (8)0.0212 (3)
H330.27910.74200.03820.025*
C340.16058 (16)0.64622 (16)0.01210 (10)0.0366 (4)
H34A0.07880.66850.03600.044*
H34B0.16300.56390.02660.044*
C350.15090 (18)0.7216 (2)0.09558 (11)0.0500 (5)
H35A0.07240.70570.11900.060*
H35B0.13490.80440.07890.060*
C360.27857 (18)0.69924 (17)0.16885 (10)0.0420 (4)
H36A0.28660.62030.19260.050*
H36B0.27210.75570.21910.050*
C370.40359 (17)0.70969 (16)0.13409 (10)0.0396 (4)
H37A0.40130.79130.11770.048*
H37B0.48550.68860.18240.048*
C380.41236 (16)0.63067 (15)0.05174 (10)0.0341 (4)
H38A0.42210.54850.06900.041*
H38B0.49330.64140.02900.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0404 (6)0.0234 (5)0.0288 (5)0.0085 (5)0.0196 (5)0.0036 (4)
O20.0373 (6)0.0238 (5)0.0317 (6)0.0083 (5)0.0171 (5)0.0063 (4)
O30.0244 (5)0.0281 (5)0.0247 (5)0.0058 (4)0.0105 (4)0.0048 (4)
O40.0340 (6)0.0294 (6)0.0279 (5)0.0096 (5)0.0143 (5)0.0079 (4)
N10.0314 (7)0.0205 (6)0.0225 (6)0.0027 (5)0.0135 (5)0.0004 (5)
N20.0256 (7)0.0191 (6)0.0340 (7)0.0043 (5)0.0127 (5)0.0072 (5)
N30.0245 (7)0.0331 (7)0.0204 (6)0.0086 (5)0.0089 (5)0.0056 (5)
N40.0289 (7)0.0229 (6)0.0168 (6)0.0061 (5)0.0069 (5)0.0039 (5)
C10.0196 (7)0.0203 (7)0.0208 (7)0.0009 (5)0.0054 (6)0.0015 (5)
C20.0209 (7)0.0189 (7)0.0204 (7)0.0024 (5)0.0067 (6)0.0007 (5)
C30.0210 (7)0.0169 (7)0.0195 (7)0.0048 (5)0.0053 (5)0.0013 (5)
C40.0217 (7)0.0197 (7)0.0158 (6)0.0036 (5)0.0039 (5)0.0011 (5)
C50.0217 (7)0.0205 (7)0.0172 (6)0.0012 (6)0.0051 (5)0.0009 (5)
C60.0208 (7)0.0244 (7)0.0150 (6)0.0022 (6)0.0031 (5)0.0004 (5)
C70.0214 (7)0.0212 (7)0.0180 (7)0.0003 (6)0.0049 (6)0.0003 (5)
C80.0228 (7)0.0182 (7)0.0224 (7)0.0040 (6)0.0033 (6)0.0008 (5)
C90.0253 (8)0.0275 (8)0.0230 (7)0.0049 (6)0.0000 (6)0.0051 (6)
C100.0255 (8)0.0294 (8)0.0301 (8)0.0031 (6)0.0031 (6)0.0027 (6)
C110.0187 (7)0.0218 (7)0.0190 (7)0.0025 (6)0.0032 (5)0.0013 (5)
C120.0314 (8)0.0198 (7)0.0227 (7)0.0042 (6)0.0102 (6)0.0015 (6)
C130.0321 (9)0.0250 (8)0.0439 (9)0.0027 (7)0.0103 (7)0.0057 (7)
C140.0411 (10)0.0248 (8)0.0470 (10)0.0011 (7)0.0085 (8)0.0107 (7)
C150.0528 (11)0.0222 (8)0.0428 (10)0.0104 (7)0.0192 (8)0.0002 (7)
C160.0361 (9)0.0336 (9)0.0397 (9)0.0130 (7)0.0077 (7)0.0033 (7)
C170.0331 (9)0.0309 (8)0.0284 (8)0.0067 (7)0.0055 (7)0.0047 (6)
C180.0232 (7)0.0207 (7)0.0148 (6)0.0015 (6)0.0028 (5)0.0006 (5)
C190.0227 (7)0.0189 (7)0.0258 (7)0.0033 (6)0.0081 (6)0.0064 (6)
C200.0374 (9)0.0261 (8)0.0220 (7)0.0024 (7)0.0050 (6)0.0011 (6)
C210.0352 (9)0.0264 (8)0.0344 (8)0.0066 (7)0.0020 (7)0.0044 (7)
C220.0382 (10)0.0339 (9)0.0522 (11)0.0028 (7)0.0240 (8)0.0164 (8)
C230.0589 (11)0.0354 (9)0.0273 (8)0.0039 (8)0.0226 (8)0.0057 (7)
C240.0410 (9)0.0248 (8)0.0213 (7)0.0020 (7)0.0071 (7)0.0006 (6)
C250.0208 (7)0.0229 (7)0.0153 (6)0.0022 (6)0.0029 (5)0.0027 (5)
C260.0307 (8)0.0416 (9)0.0267 (8)0.0173 (7)0.0118 (7)0.0101 (7)
C270.0486 (11)0.0472 (11)0.0447 (10)0.0254 (9)0.0072 (8)0.0071 (8)
C280.0569 (13)0.0299 (10)0.0952 (17)0.0139 (9)0.0306 (12)0.0101 (10)
C290.0608 (13)0.0714 (14)0.0543 (12)0.0304 (11)0.0254 (11)0.0356 (11)
C300.0386 (10)0.0752 (14)0.0286 (9)0.0247 (9)0.0038 (7)0.0053 (9)
C310.0250 (8)0.0467 (10)0.0451 (10)0.0119 (7)0.0049 (7)0.0021 (8)
C320.0215 (7)0.0207 (7)0.0190 (7)0.0001 (6)0.0035 (6)0.0011 (5)
C330.0275 (8)0.0201 (7)0.0150 (6)0.0009 (6)0.0048 (6)0.0031 (5)
C340.0281 (8)0.0594 (11)0.0224 (8)0.0087 (8)0.0067 (7)0.0107 (7)
C350.0335 (10)0.0823 (15)0.0345 (9)0.0053 (9)0.0149 (8)0.0222 (9)
C360.0517 (11)0.0560 (11)0.0196 (8)0.0109 (9)0.0107 (7)0.0109 (7)
C370.0350 (9)0.0546 (11)0.0240 (8)0.0044 (8)0.0005 (7)0.0127 (8)
C380.0256 (8)0.0460 (10)0.0261 (8)0.0015 (7)0.0031 (6)0.0093 (7)
Geometric parameters (Å, º) top
O1—C111.2401 (16)C16—H16B0.9900
O2—C181.2363 (17)C17—H17A0.9900
O3—C251.2389 (16)C17—H17B0.9900
O4—C321.2384 (17)C19—C241.516 (2)
N1—C111.3219 (18)C19—C201.521 (2)
N1—C121.4625 (17)C19—H191.0000
N1—H010.900 (18)C20—C211.524 (2)
N2—C181.3233 (18)C20—H20A0.9900
N2—C191.4635 (17)C20—H20B0.9900
N2—H020.895 (18)C21—C221.508 (2)
N3—C251.3317 (18)C21—H21A0.9900
N3—C261.4657 (19)C21—H21B0.9900
N3—H030.927 (17)C22—C231.512 (2)
N4—C321.3275 (17)C22—H22A0.9900
N4—C331.4622 (17)C22—H22B0.9900
N4—H040.953 (19)C23—C241.524 (2)
C1—C111.4988 (18)C23—H23A0.9900
C1—C21.5259 (19)C23—H23B0.9900
C1—C71.5543 (19)C24—H24A0.9900
C1—C51.5572 (18)C24—H24B0.9900
C2—C31.4788 (18)C26—C311.519 (2)
C2—C71.5175 (19)C26—C271.530 (2)
C2—H21.0000C26—H261.0000
C3—C81.3343 (19)C27—C281.522 (3)
C3—C41.4791 (19)C27—H27A0.9900
C4—C51.5268 (18)C27—H27B0.9900
C4—C61.5298 (18)C28—C291.529 (3)
C4—H41.0000C28—H28A0.9900
C5—C181.5004 (18)C28—H28B0.9900
C5—C61.5545 (19)C29—C301.500 (3)
C6—C251.4978 (19)C29—H29A0.9900
C6—C71.5509 (18)C29—H29B0.9900
C7—C321.4982 (18)C30—C311.514 (2)
C8—C101.5008 (19)C30—H30A0.9900
C8—C91.5014 (19)C30—H30B0.9900
C9—H9A0.9800C31—H31A0.9900
C9—H9B0.9800C31—H31B0.9900
C9—H9C0.9800C33—C341.507 (2)
C10—H10A0.9800C33—C381.512 (2)
C10—H10B0.9800C33—H331.0000
C10—H10C0.9800C34—C351.519 (2)
C12—C171.518 (2)C34—H34A0.9900
C12—C131.524 (2)C34—H34B0.9900
C12—H121.0000C35—C361.512 (3)
C13—C141.525 (2)C35—H35A0.9900
C13—H13A0.9900C35—H35B0.9900
C13—H13B0.9900C36—C371.508 (2)
C14—C151.519 (2)C36—H36A0.9900
C14—H14A0.9900C36—H36B0.9900
C14—H14B0.9900C37—C381.527 (2)
C15—C161.516 (2)C37—H37A0.9900
C15—H15A0.9900C37—H37B0.9900
C15—H15B0.9900C38—H38A0.9900
C16—C171.527 (2)C38—H38B0.9900
C16—H16A0.9900
C11—N1—C12124.02 (12)N2—C19—H19108.4
C11—N1—H01117.3 (11)C24—C19—H19108.4
C12—N1—H01118.6 (11)C20—C19—H19108.4
C18—N2—C19123.04 (12)C19—C20—C21111.42 (12)
C18—N2—H02117.5 (11)C19—C20—H20A109.3
C19—N2—H02119.4 (11)C21—C20—H20A109.3
C25—N3—C26123.43 (12)C19—C20—H20B109.3
C25—N3—H03116.0 (10)C21—C20—H20B109.3
C26—N3—H03120.5 (10)H20A—C20—H20B108.0
C32—N4—C33122.40 (12)C22—C21—C20112.27 (13)
C32—N4—H04117.1 (11)C22—C21—H21A109.2
C33—N4—H04120.2 (11)C20—C21—H21A109.2
C11—C1—C2119.79 (11)C22—C21—H21B109.2
C11—C1—C7128.02 (11)C20—C21—H21B109.2
C2—C1—C759.02 (9)H21A—C21—H21B107.9
C11—C1—C5132.38 (11)C21—C22—C23111.15 (13)
C2—C1—C5103.77 (10)C21—C22—H22A109.4
C7—C1—C589.55 (10)C23—C22—H22A109.4
C3—C2—C7110.32 (11)C21—C22—H22B109.4
C3—C2—C1109.86 (11)C23—C22—H22B109.4
C7—C2—C161.42 (9)H22A—C22—H22B108.0
C3—C2—H2120.4C22—C23—C24110.96 (13)
C7—C2—H2120.4C22—C23—H23A109.4
C1—C2—H2120.4C24—C23—H23A109.4
C8—C3—C2128.92 (12)C22—C23—H23B109.4
C8—C3—C4130.05 (12)C24—C23—H23B109.4
C2—C3—C4101.04 (11)H23A—C23—H23B108.0
C3—C4—C5110.15 (11)C19—C24—C23111.47 (12)
C3—C4—C6109.42 (11)C19—C24—H24A109.3
C5—C4—C661.14 (9)C23—C24—H24A109.3
C3—C4—H4120.6C19—C24—H24B109.3
C5—C4—H4120.6C23—C24—H24B109.3
C6—C4—H4120.6H24A—C24—H24B108.0
C18—C5—C4121.36 (11)O3—C25—N3123.74 (13)
C18—C5—C6133.19 (12)O3—C25—C6119.69 (12)
C4—C5—C659.53 (8)N3—C25—C6116.53 (12)
C18—C5—C1128.07 (11)N3—C26—C31110.80 (12)
C4—C5—C1103.73 (10)N3—C26—C27110.47 (13)
C6—C5—C190.21 (10)C31—C26—C27109.57 (13)
C25—C6—C4118.91 (11)N3—C26—H26108.6
C25—C6—C7132.13 (11)C31—C26—H26108.6
C4—C6—C7103.97 (11)C27—C26—H26108.6
C25—C6—C5129.19 (12)C28—C27—C26112.03 (14)
C4—C6—C559.33 (8)C28—C27—H27A109.2
C7—C6—C589.78 (10)C26—C27—H27A109.2
C32—C7—C2120.34 (11)C28—C27—H27B109.2
C32—C7—C6128.80 (12)C26—C27—H27B109.2
C2—C7—C6103.83 (10)H27A—C27—H27B107.9
C32—C7—C1132.80 (12)C27—C28—C29111.24 (16)
C2—C7—C159.56 (9)C27—C28—H28A109.4
C6—C7—C190.45 (10)C29—C28—H28A109.4
C3—C8—C10122.13 (12)C27—C28—H28B109.4
C3—C8—C9123.10 (12)C29—C28—H28B109.4
C10—C8—C9114.77 (12)H28A—C28—H28B108.0
C8—C9—H9A109.5C30—C29—C28111.36 (15)
C8—C9—H9B109.5C30—C29—H29A109.4
H9A—C9—H9B109.5C28—C29—H29A109.4
C8—C9—H9C109.5C30—C29—H29B109.4
H9A—C9—H9C109.5C28—C29—H29B109.4
H9B—C9—H9C109.5H29A—C29—H29B108.0
C8—C10—H10A109.5C29—C30—C31111.21 (15)
C8—C10—H10B109.5C29—C30—H30A109.4
H10A—C10—H10B109.5C31—C30—H30A109.4
C8—C10—H10C109.5C29—C30—H30B109.4
H10A—C10—H10C109.5C31—C30—H30B109.4
H10B—C10—H10C109.5H30A—C30—H30B108.0
O1—C11—N1124.17 (13)C30—C31—C26111.95 (14)
O1—C11—C1119.63 (12)C30—C31—H31A109.2
N1—C11—C1116.19 (12)C26—C31—H31A109.2
N1—C12—C17110.63 (11)C30—C31—H31B109.2
N1—C12—C13108.98 (12)C26—C31—H31B109.2
C17—C12—C13111.38 (12)H31A—C31—H31B107.9
N1—C12—H12108.6O4—C32—N4123.06 (12)
C17—C12—H12108.6O4—C32—C7120.21 (12)
C13—C12—H12108.6N4—C32—C7116.63 (12)
C12—C13—C14111.82 (13)N4—C33—C34108.57 (12)
C12—C13—H13A109.3N4—C33—C38113.61 (11)
C14—C13—H13A109.3C34—C33—C38110.74 (12)
C12—C13—H13B109.3N4—C33—H33107.9
C14—C13—H13B109.3C34—C33—H33107.9
H13A—C13—H13B107.9C38—C33—H33107.9
C15—C14—C13111.47 (13)C33—C34—C35111.46 (14)
C15—C14—H14A109.3C33—C34—H34A109.3
C13—C14—H14A109.3C35—C34—H34A109.3
C15—C14—H14B109.3C33—C34—H34B109.3
C13—C14—H14B109.3C35—C34—H34B109.3
H14A—C14—H14B108.0H34A—C34—H34B108.0
C16—C15—C14110.50 (13)C36—C35—C34111.95 (15)
C16—C15—H15A109.5C36—C35—H35A109.2
C14—C15—H15A109.5C34—C35—H35A109.2
C16—C15—H15B109.5C36—C35—H35B109.2
C14—C15—H15B109.5C34—C35—H35B109.2
H15A—C15—H15B108.1H35A—C35—H35B107.9
C15—C16—C17111.20 (13)C37—C36—C35111.54 (14)
C15—C16—H16A109.4C37—C36—H36A109.3
C17—C16—H16A109.4C35—C36—H36A109.3
C15—C16—H16B109.4C37—C36—H36B109.3
C17—C16—H16B109.4C35—C36—H36B109.3
H16A—C16—H16B108.0H36A—C36—H36B108.0
C12—C17—C16111.79 (12)C36—C37—C38111.32 (14)
C12—C17—H17A109.3C36—C37—H37A109.4
C16—C17—H17A109.3C38—C37—H37A109.4
C12—C17—H17B109.3C36—C37—H37B109.4
C16—C17—H17B109.3C38—C37—H37B109.4
H17A—C17—H17B107.9H37A—C37—H37B108.0
O2—C18—N2123.31 (13)C33—C38—C37110.07 (12)
O2—C18—C5120.24 (12)C33—C38—H38A109.6
N2—C18—C5116.36 (12)C37—C38—H38A109.6
N2—C19—C24109.22 (11)C33—C38—H38B109.6
N2—C19—C20111.59 (11)C37—C38—H38B109.6
C24—C19—C20110.83 (12)H38A—C38—H38B108.2
C11—C1—C2—C3138.11 (12)C7—C1—C11—O134.0 (2)
C7—C1—C2—C3102.93 (12)C5—C1—C11—O1168.41 (13)
C5—C1—C2—C321.93 (14)C2—C1—C11—N1140.90 (13)
C11—C1—C2—C7118.96 (13)C7—C1—C11—N1146.87 (13)
C5—C1—C2—C781.00 (10)C5—C1—C11—N112.4 (2)
C7—C2—C3—C8147.78 (14)C11—N1—C12—C17105.53 (15)
C1—C2—C3—C8146.33 (14)C11—N1—C12—C13131.70 (14)
C7—C2—C3—C432.59 (13)N1—C12—C13—C14175.38 (13)
C1—C2—C3—C433.29 (13)C17—C12—C13—C1453.06 (17)
C8—C3—C4—C5147.19 (14)C12—C13—C14—C1554.80 (18)
C2—C3—C4—C532.43 (13)C13—C14—C15—C1656.37 (18)
C8—C3—C4—C6147.38 (14)C14—C15—C16—C1756.67 (18)
C2—C3—C4—C633.00 (13)N1—C12—C17—C16174.86 (12)
C3—C4—C5—C18133.49 (13)C13—C12—C17—C1653.50 (17)
C6—C4—C5—C18124.85 (14)C15—C16—C17—C1255.70 (18)
C3—C4—C5—C6101.67 (12)C19—N2—C18—O24.8 (2)
C3—C4—C5—C119.68 (14)C19—N2—C18—C5171.89 (12)
C6—C4—C5—C181.99 (11)C4—C5—C18—O2117.87 (14)
C11—C1—C5—C184.4 (2)C6—C5—C18—O2166.16 (13)
C2—C1—C5—C18151.99 (13)C1—C5—C18—O228.3 (2)
C7—C1—C5—C18150.15 (13)C4—C5—C18—N258.95 (17)
C11—C1—C5—C4155.06 (14)C6—C5—C18—N217.0 (2)
C2—C1—C5—C41.30 (13)C1—C5—C18—N2154.90 (13)
C7—C1—C5—C459.17 (11)C18—N2—C19—C24134.34 (14)
C11—C1—C5—C6146.35 (14)C18—N2—C19—C20102.78 (16)
C2—C1—C5—C657.29 (11)N2—C19—C20—C21175.97 (13)
C7—C1—C5—C60.58 (10)C24—C19—C20—C2154.01 (17)
C3—C4—C6—C25136.36 (12)C19—C20—C21—C2253.91 (18)
C5—C4—C6—C25120.78 (14)C20—C21—C22—C2354.58 (19)
C3—C4—C6—C721.62 (14)C21—C22—C23—C2455.53 (19)
C5—C4—C6—C781.25 (11)N2—C19—C24—C23179.05 (13)
C3—C4—C6—C5102.87 (12)C20—C19—C24—C2355.72 (17)
C18—C5—C6—C252.0 (2)C22—C23—C24—C1956.61 (18)
C4—C5—C6—C25103.99 (15)C26—N3—C25—O30.5 (2)
C1—C5—C6—C25150.15 (13)C26—N3—C25—C6178.21 (13)
C18—C5—C6—C4106.02 (16)C4—C6—C25—O342.36 (18)
C1—C5—C6—C4105.85 (10)C7—C6—C25—O3167.02 (13)
C18—C5—C6—C7147.55 (14)C5—C6—C25—O330.1 (2)
C4—C5—C6—C7106.44 (10)C4—C6—C25—N3135.48 (13)
C1—C5—C6—C70.58 (10)C7—C6—C25—N315.1 (2)
C3—C2—C7—C32133.13 (13)C5—C6—C25—N3152.06 (13)
C1—C2—C7—C32124.70 (14)C25—N3—C26—C31114.08 (15)
C3—C2—C7—C619.94 (14)C25—N3—C26—C27124.30 (15)
C1—C2—C7—C682.23 (11)N3—C26—C27—C2867.47 (18)
C3—C2—C7—C1102.17 (12)C31—C26—C27—C2854.87 (19)
C25—C6—C7—C322.8 (2)C26—C27—C28—C2954.3 (2)
C4—C6—C7—C32150.94 (13)C27—C28—C29—C3054.2 (2)
C5—C6—C7—C32150.84 (13)C28—C29—C30—C3155.5 (2)
C25—C6—C7—C2152.70 (14)C29—C30—C31—C2657.38 (19)
C4—C6—C7—C21.03 (13)N3—C26—C31—C3065.98 (18)
C5—C6—C7—C259.26 (11)C27—C26—C31—C3056.17 (18)
C25—C6—C7—C1148.62 (14)C33—N4—C32—O46.4 (2)
C4—C6—C7—C157.64 (11)C33—N4—C32—C7169.92 (12)
C5—C6—C7—C10.58 (10)C2—C7—C32—O4117.39 (15)
C11—C1—C7—C320.7 (2)C6—C7—C32—O428.3 (2)
C2—C1—C7—C32104.73 (16)C1—C7—C32—O4167.58 (13)
C5—C1—C7—C32148.88 (14)C2—C7—C32—N459.03 (17)
C11—C1—C7—C2105.44 (15)C6—C7—C32—N4155.32 (13)
C5—C1—C7—C2106.40 (10)C1—C7—C32—N416.0 (2)
C11—C1—C7—C6148.75 (13)C32—N4—C33—C34153.87 (13)
C2—C1—C7—C6105.82 (10)C32—N4—C33—C3882.45 (17)
C5—C1—C7—C60.58 (10)N4—C33—C34—C35178.12 (14)
C2—C3—C8—C102.4 (2)C38—C33—C34—C3556.50 (19)
C4—C3—C8—C10178.04 (14)C33—C34—C35—C3653.8 (2)
C2—C3—C8—C9176.49 (13)C34—C35—C36—C3752.9 (2)
C4—C3—C8—C93.0 (2)C35—C36—C37—C3854.7 (2)
C12—N1—C11—O11.7 (2)N4—C33—C38—C37179.62 (13)
C12—N1—C11—C1179.23 (12)C34—C33—C38—C3757.89 (18)
C2—C1—C11—O138.25 (18)C36—C37—C38—C3357.17 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H01···O20.900 (18)1.824 (18)2.7091 (15)167.4 (17)
N2—H02···O30.895 (18)1.907 (19)2.7841 (16)166.2 (16)
N3—H03···O40.927 (17)1.804 (17)2.7153 (15)167.2 (15)
N4—H04···O10.953 (19)1.81 (2)2.7490 (16)166.5 (16)
C4—H4···O3i1.002.393.3890 (16)174
C9—H9A···O3i0.982.503.4717 (18)170
C14—H14B···O4ii0.992.503.367 (2)146
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1, z.
 

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