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In the title compound, C20H32N6O6, the five-membered imidazolone rings adopt envelope conformations. The six-membered rings are in chair conformations. The crystal packing is stabilized by C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042644/sj2144sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042644/sj2144Isup2.hkl
Contains datablock I

CCDC reference: 622511

Key indicators

  • Single-crystal X-ray study
  • T = 292 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.064
  • wR factor = 0.197
  • Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C14
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.625 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.02 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.62 e/A    PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.50 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.79 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O6' PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 29.00 Deg. C11' -C10 -H10B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 24.10 Deg. C11 -C10 -H10C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 24.70 Deg. H10A -C10 -H10D 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 32.40 Deg. C10 -C11 -H10C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.50 Deg. O6 -C13 -O6' 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 15 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 13 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Diethyl 2,6-diisopropyl-4,8-dioxoperhydro-2,3a,4a,6,7a,8a- hexaazacyclopenta[def]fluorene-8 b,8c-dicarboxylate top
Crystal data top
C20H32N6O6F(000) = 968
Mr = 452.52Dx = 1.356 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4685 reflections
a = 11.4577 (15) Åθ = 2.4–24.8°
b = 9.2015 (13) ŵ = 0.10 mm1
c = 21.164 (3) ÅT = 292 K
β = 96.621 (2)°Block, colorless
V = 2216.4 (5) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2920 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
φ and ω scansh = 1313
10681 measured reflectionsk = 710
3883 independent reflectionsl = 2325
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.1136P)2 + 0.6272P]
where P = (Fo2 + 2Fc2)/3
3883 reflections(Δ/σ)max = 0.010
323 parametersΔρmax = 0.63 e Å3
6 restraintsΔρmin = 0.31 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)
C10.6073 (3)0.8703 (5)0.1107 (2)0.1155 (13)
H1A0.60560.97410.11520.173*
H1B0.60210.84570.06630.173*
H1C0.67940.83310.13220.173*
C20.3910 (3)0.8675 (6)0.10168 (18)0.1161 (13)
H2A0.32200.81950.11300.174*
H2B0.39600.85440.05710.174*
H2C0.38650.96940.11090.174*
C30.5010 (3)0.8019 (4)0.14032 (17)0.0886 (9)
H30.50130.69610.13490.106*
C40.4031 (2)0.8055 (3)0.23705 (15)0.0736 (7)
H4A0.33400.82930.20800.088*
H4B0.40310.86760.27410.088*
C50.6105 (2)0.7840 (3)0.24423 (16)0.0759 (8)
H5A0.62470.84330.28220.091*
H5B0.67730.79570.22040.091*
C60.33226 (18)0.5467 (3)0.22114 (12)0.0595 (6)
C70.63975 (18)0.5165 (3)0.22799 (12)0.0606 (6)
C80.49889 (18)0.5923 (3)0.29224 (12)0.0583 (6)
C90.5107 (2)0.6420 (3)0.36224 (13)0.0715 (7)
C100.6286 (4)0.6224 (6)0.46011 (17)0.1132 (13)
H10A0.55520.64530.47660.136*0.579 (7)
H10B0.68180.70410.46810.136*0.579 (7)
H10C0.69010.56200.47880.136*0.421 (7)
H10D0.55750.60070.47860.136*0.421 (7)
C110.6809 (12)0.4892 (12)0.4900 (5)0.199 (4)0.579 (7)
H11A0.62150.43490.50820.299*0.579 (7)
H11B0.74240.51500.52280.299*0.579 (7)
H11C0.71280.43110.45840.299*0.579 (7)
C11'0.6529 (15)0.7776 (12)0.4806 (7)0.199 (4)0.421 (7)
H11D0.73610.79460.48550.299*0.421 (7)
H11E0.62260.79470.52040.299*0.421 (7)
H11F0.61540.84230.44890.299*0.421 (7)
C120.48730 (18)0.4253 (3)0.28070 (11)0.0569 (6)
C130.4805 (2)0.3345 (3)0.34084 (13)0.0699 (7)
C140.5209 (7)0.1052 (9)0.3912 (4)0.108 (2)0.684 (9)
H14A0.44900.12570.40970.129*0.684 (9)
H14B0.51590.00730.37400.129*0.684 (9)
C150.6199 (8)0.1173 (17)0.4387 (5)0.199 (6)0.684 (9)
H15A0.68960.08720.42110.299*0.684 (9)
H15B0.60820.05630.47420.299*0.684 (9)
H15C0.62840.21640.45260.299*0.684 (9)
O60.5357 (5)0.2084 (5)0.3414 (4)0.0824 (15)0.684 (9)
C14'0.573 (3)0.172 (2)0.4103 (8)0.152 (9)0.316 (9)
H14C0.49980.19390.42690.182*0.316 (9)
H14D0.63640.20730.44090.182*0.316 (9)
C15'0.584 (2)0.012 (2)0.4049 (12)0.199 (6)0.316 (9)
H15D0.62560.01130.36920.299*0.316 (9)
H15E0.50760.03130.39900.299*0.316 (9)
H15F0.62720.02600.44310.299*0.316 (9)
O6'0.5765 (9)0.2524 (14)0.3503 (9)0.091 (4)0.316 (9)
C160.3639 (2)0.2820 (3)0.19963 (12)0.0656 (7)
H16A0.36000.19650.22610.079*
H16B0.29080.28820.17170.079*
C170.5701 (2)0.2635 (3)0.20300 (13)0.0673 (7)
H17A0.63470.26010.17720.081*
H17B0.57340.17580.22860.081*
C180.4553 (3)0.3631 (3)0.10532 (13)0.0736 (7)
H180.46250.46400.12010.088*
C190.5560 (3)0.3291 (5)0.06708 (16)0.1059 (11)
H19A0.62910.35450.09140.159*
H19B0.54690.38420.02830.159*
H19C0.55580.22730.05730.159*
C200.3403 (3)0.3453 (5)0.06353 (16)0.1051 (11)
H20A0.33000.24520.05140.158*
H20B0.34080.40430.02620.158*
H20C0.27680.37520.08650.158*
N10.50701 (18)0.8369 (3)0.20629 (12)0.0790 (7)
N20.39475 (15)0.6520 (2)0.25720 (10)0.0596 (5)
N30.60335 (15)0.6303 (2)0.26333 (10)0.0614 (5)
N40.37556 (15)0.4119 (2)0.24068 (9)0.0577 (5)
N50.58585 (15)0.3908 (2)0.24580 (9)0.0595 (5)
N60.46019 (18)0.2653 (2)0.16136 (10)0.0651 (6)
O10.24938 (14)0.5685 (2)0.18158 (9)0.0754 (5)
O20.71177 (14)0.5239 (2)0.19057 (10)0.0777 (6)
O30.4415 (2)0.7187 (3)0.38417 (11)0.0983 (7)
O40.60861 (18)0.5906 (3)0.39258 (9)0.0881 (6)
O50.4165 (2)0.3683 (3)0.37911 (10)0.0911 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.091 (2)0.154 (4)0.106 (3)0.002 (2)0.032 (2)0.010 (3)
C20.083 (2)0.173 (4)0.089 (2)0.010 (2)0.0016 (18)0.005 (2)
C30.0761 (18)0.082 (2)0.109 (2)0.0035 (15)0.0133 (17)0.0172 (18)
C40.0525 (14)0.0733 (17)0.0963 (19)0.0087 (12)0.0141 (13)0.0081 (15)
C50.0494 (13)0.0752 (18)0.104 (2)0.0060 (12)0.0117 (13)0.0076 (15)
C60.0364 (11)0.0729 (16)0.0708 (14)0.0020 (10)0.0131 (10)0.0013 (12)
C70.0354 (11)0.0724 (16)0.0742 (14)0.0033 (10)0.0076 (10)0.0093 (12)
C80.0413 (11)0.0659 (15)0.0682 (14)0.0000 (10)0.0080 (10)0.0010 (11)
C90.0605 (15)0.0773 (17)0.0768 (17)0.0068 (13)0.0078 (13)0.0100 (14)
C100.123 (3)0.139 (3)0.074 (2)0.011 (3)0.008 (2)0.011 (2)
C110.195 (9)0.265 (12)0.133 (6)0.012 (9)0.002 (6)0.033 (8)
C11'0.195 (9)0.265 (12)0.133 (6)0.012 (9)0.002 (6)0.033 (8)
C120.0445 (11)0.0662 (15)0.0608 (13)0.0012 (10)0.0101 (10)0.0007 (11)
C130.0697 (16)0.0774 (18)0.0634 (15)0.0040 (14)0.0114 (12)0.0032 (13)
C140.133 (5)0.095 (5)0.089 (4)0.001 (4)0.019 (3)0.015 (3)
C150.151 (8)0.281 (17)0.157 (9)0.025 (8)0.016 (6)0.062 (9)
O60.092 (3)0.072 (3)0.082 (2)0.006 (2)0.007 (3)0.022 (2)
C14'0.23 (3)0.133 (16)0.084 (11)0.049 (16)0.024 (12)0.052 (11)
C15'0.151 (8)0.281 (17)0.157 (9)0.025 (8)0.016 (6)0.062 (9)
O6'0.100 (8)0.070 (6)0.107 (8)0.017 (6)0.028 (7)0.029 (6)
C160.0595 (14)0.0669 (16)0.0714 (15)0.0112 (11)0.0120 (12)0.0003 (12)
C170.0630 (14)0.0660 (16)0.0750 (15)0.0091 (12)0.0173 (12)0.0001 (13)
C180.0850 (18)0.0677 (16)0.0699 (15)0.0049 (13)0.0168 (14)0.0013 (13)
C190.115 (3)0.127 (3)0.083 (2)0.001 (2)0.0387 (19)0.010 (2)
C200.107 (3)0.130 (3)0.0764 (19)0.010 (2)0.0014 (18)0.012 (2)
N10.0571 (12)0.0857 (16)0.0953 (17)0.0028 (11)0.0134 (11)0.0140 (13)
N20.0404 (9)0.0639 (12)0.0749 (12)0.0039 (8)0.0087 (8)0.0010 (10)
N30.0405 (9)0.0667 (13)0.0774 (13)0.0001 (8)0.0090 (9)0.0030 (10)
N40.0428 (9)0.0659 (12)0.0651 (11)0.0030 (8)0.0089 (8)0.0004 (9)
N50.0436 (9)0.0680 (13)0.0679 (12)0.0055 (8)0.0110 (8)0.0008 (10)
N60.0674 (12)0.0627 (13)0.0668 (12)0.0035 (10)0.0151 (10)0.0021 (10)
O10.0454 (9)0.0889 (13)0.0899 (12)0.0044 (8)0.0014 (9)0.0017 (10)
O20.0498 (9)0.0884 (13)0.0997 (13)0.0076 (8)0.0286 (9)0.0099 (11)
O30.0982 (15)0.1089 (17)0.0901 (14)0.0148 (13)0.0204 (12)0.0255 (13)
O40.0753 (12)0.1164 (17)0.0695 (11)0.0006 (11)0.0046 (10)0.0079 (11)
O50.1038 (15)0.0980 (15)0.0773 (12)0.0060 (12)0.0355 (12)0.0057 (11)
Geometric parameters (Å, º) top
C1—C31.565 (5)C11'—H11D0.9600
C1—H1A0.9600C11'—H11E0.9600
C1—H1B0.9600C11'—H11F0.9600
C1—H1C0.9600C12—N51.454 (3)
C2—C31.544 (5)C12—N41.457 (3)
C2—H2A0.9600C12—C131.532 (4)
C2—H2B0.9600C13—O51.195 (3)
C2—H2C0.9600C13—O61.321 (5)
C3—N11.427 (4)C13—O6'1.330 (8)
C3—H30.9800C14—C151.431 (7)
C4—N11.450 (3)C14—O61.444 (10)
C4—N21.482 (4)C14—H14A0.9700
C4—H4A0.9700C14—H14B0.9700
C4—H4B0.9700C15—H15A0.9600
C5—N11.438 (4)C15—H15B0.9600
C5—N31.476 (3)C15—H15C0.9600
C5—H5A0.9700C14'—O6'1.47 (2)
C5—H5B0.9700C14'—C15'1.488 (9)
C6—O11.208 (3)C14'—H14C0.9700
C6—N21.381 (3)C14'—H14D0.9700
C6—N41.382 (3)C15'—H15D0.9600
C7—O21.210 (3)C15'—H15E0.9600
C7—N31.379 (3)C15'—H15F0.9600
C7—N51.384 (3)C16—N61.450 (3)
C8—N21.439 (3)C16—N41.474 (3)
C8—N31.449 (3)C16—H16A0.9700
C8—C91.541 (4)C16—H16B0.9700
C8—C121.559 (4)C17—N61.452 (3)
C9—O31.194 (3)C17—N51.479 (3)
C9—O41.315 (3)C17—H17A0.9700
C10—O41.451 (4)C17—H17B0.9700
C10—C111.474 (8)C18—N61.484 (3)
C10—C11'1.509 (9)C18—C201.509 (4)
C10—H10A0.9700C18—C191.516 (4)
C10—H10B0.9700C18—H180.9800
C10—H10C0.9475C19—H19A0.9600
C10—H10D0.9643C19—H19B0.9600
C11—H10C0.7223C19—H19C0.9600
C11—H11A0.9600C20—H20A0.9600
C11—H11B0.9600C20—H20B0.9600
C11—H11C0.9600C20—H20C0.9600
C3—C1—H1A109.5N5—C12—C13114.8 (2)
C3—C1—H1B109.5N4—C12—C13108.15 (19)
H1A—C1—H1B109.5N5—C12—C8103.75 (18)
C3—C1—H1C109.5N4—C12—C8103.18 (18)
H1A—C1—H1C109.5C13—C12—C8114.8 (2)
H1B—C1—H1C109.5O5—C13—O6123.6 (4)
C3—C2—H2A109.5O5—C13—O6'127.4 (8)
C3—C2—H2B109.5O6—C13—O6'27.5 (6)
H2A—C2—H2B109.5O5—C13—C12121.0 (2)
C3—C2—H2C109.5O6—C13—C12114.6 (4)
H2A—C2—H2C109.5O6'—C13—C12108.4 (7)
H2B—C2—H2C109.5C15—C14—O6108.1 (8)
N1—C3—C2112.0 (3)C15—C14—H14A110.1
N1—C3—C1110.5 (3)O6—C14—H14A110.1
C2—C3—C1104.8 (3)C15—C14—H14B110.1
N1—C3—H3109.8O6—C14—H14B110.1
C2—C3—H3109.8H14A—C14—H14B108.4
C1—C3—H3109.8C13—O6—C14119.2 (7)
N1—C4—N2113.7 (2)O6'—C14'—C15'114.9 (17)
N1—C4—H4A108.8O6'—C14'—H14C108.6
N2—C4—H4A108.8C15'—C14'—H14C108.6
N1—C4—H4B108.8O6'—C14'—H14D108.5
N2—C4—H4B108.8C15'—C14'—H14D108.5
H4A—C4—H4B107.7H14C—C14'—H14D107.5
N1—C5—N3114.1 (2)C14'—C15'—H15D109.5
N1—C5—H5A108.7C14'—C15'—H15E109.5
N3—C5—H5A108.7H15D—C15'—H15E109.5
N1—C5—H5B108.7C14'—C15'—H15F109.5
N3—C5—H5B108.7H15D—C15'—H15F109.5
H5A—C5—H5B107.6H15E—C15'—H15F109.5
O1—C6—N2125.6 (2)C13—O6'—C14'108.2 (14)
O1—C6—N4125.6 (2)N6—C16—N4113.07 (19)
N2—C6—N4108.61 (19)N6—C16—H16A109.0
O2—C7—N3125.8 (2)N4—C16—H16A109.0
O2—C7—N5125.8 (2)N6—C16—H16B109.0
N3—C7—N5108.3 (2)N4—C16—H16B109.0
N2—C8—N3111.5 (2)H16A—C16—H16B107.8
N2—C8—C9111.0 (2)N6—C17—N5113.48 (19)
N3—C8—C9110.43 (19)N6—C17—H17A108.9
N2—C8—C12104.18 (18)N5—C17—H17A108.9
N3—C8—C12103.38 (18)N6—C17—H17B108.9
C9—C8—C12116.1 (2)N5—C17—H17B108.9
O3—C9—O4126.1 (3)H17A—C17—H17B107.7
O3—C9—C8124.1 (3)N6—C18—C20110.6 (2)
O4—C9—C8109.8 (2)N6—C18—C19109.9 (3)
O4—C10—C11105.4 (6)C20—C18—C19109.4 (3)
O4—C10—C11'118.5 (7)N6—C18—H18109.0
C11—C10—C11'127.7 (8)C20—C18—H18109.0
O4—C10—H10A110.7C19—C18—H18109.0
C11—C10—H10A110.7C18—C19—H19A109.5
C11'—C10—H10A80.2C18—C19—H19B109.5
O4—C10—H10B110.7H19A—C19—H19B109.5
C11—C10—H10B110.7C18—C19—H19C109.5
C11'—C10—H10B29.0H19A—C19—H19C109.5
H10A—C10—H10B108.8H19B—C19—H19C109.5
O4—C10—H10C108.5C18—C20—H20A109.5
C11—C10—H10C24.1C18—C20—H20B109.5
C11'—C10—H10C109.4H20A—C20—H20B109.5
H10A—C10—H10C127.7C18—C20—H20C109.5
H10B—C10—H10C87.7H20A—C20—H20C109.5
O4—C10—H10D108.2H20B—C20—H20C109.5
C11—C10—H10D88.5C3—N1—C5114.4 (2)
C11'—C10—H10D102.5C3—N1—C4116.4 (2)
H10A—C10—H10D24.7C5—N1—C4110.4 (2)
H10B—C10—H10D129.2C6—N2—C8111.3 (2)
H10C—C10—H10D109.4C6—N2—C4123.8 (2)
C10—C11—H10C32.4C8—N2—C4115.79 (19)
C10—C11—H11A109.5C7—N3—C8111.23 (19)
H10C—C11—H11A138.8C7—N3—C5123.3 (2)
C10—C11—H11B109.5C8—N3—C5114.95 (19)
H10C—C11—H11B83.4C6—N4—C12111.03 (19)
C10—C11—H11C109.5C6—N4—C16123.1 (2)
H10C—C11—H11C101.9C12—N4—C16115.17 (19)
C10—C11'—H11D109.5C7—N5—C12110.67 (19)
C10—C11'—H11E109.5C7—N5—C17121.5 (2)
H11D—C11'—H11E109.5C12—N5—C17115.92 (18)
C10—C11'—H11F109.5C16—N6—C17108.96 (19)
H11D—C11'—H11F109.5C16—N6—C18114.9 (2)
H11E—C11'—H11F109.5C17—N6—C18116.2 (2)
N5—C12—N4111.60 (18)C9—O4—C10115.9 (3)
N2—C8—C9—O30.7 (4)N1—C4—N2—C695.1 (3)
N3—C8—C9—O3124.8 (3)N1—C4—N2—C848.9 (3)
C12—C8—C9—O3118.0 (3)O2—C7—N3—C8167.2 (2)
N2—C8—C9—O4177.6 (2)N5—C7—N3—C816.8 (3)
N3—C8—C9—O453.5 (3)O2—C7—N3—C524.4 (4)
C12—C8—C9—O463.8 (3)N5—C7—N3—C5159.6 (2)
N2—C8—C12—N5115.78 (18)N2—C8—N3—C7100.8 (2)
N3—C8—C12—N50.9 (2)C9—C8—N3—C7135.4 (2)
C9—C8—C12—N5121.9 (2)C12—C8—N3—C710.6 (2)
N2—C8—C12—N40.7 (2)N2—C8—N3—C545.4 (3)
N3—C8—C12—N4117.39 (18)C9—C8—N3—C578.5 (3)
C9—C8—C12—N4121.6 (2)C12—C8—N3—C5156.7 (2)
N2—C8—C12—C13118.2 (2)N1—C5—N3—C790.8 (3)
N3—C8—C12—C13125.2 (2)N1—C5—N3—C850.8 (3)
C9—C8—C12—C134.1 (3)O1—C6—N4—C12170.3 (2)
N5—C12—C13—O5167.1 (2)N2—C6—N4—C1213.4 (2)
N4—C12—C13—O567.5 (3)O1—C6—N4—C1627.6 (3)
C8—C12—C13—O547.0 (3)N2—C6—N4—C16156.10 (19)
N5—C12—C13—O622.7 (4)N5—C12—N4—C6102.3 (2)
N4—C12—C13—O6102.6 (4)C13—C12—N4—C6130.5 (2)
C8—C12—C13—O6142.8 (4)C8—C12—N4—C68.5 (2)
N5—C12—C13—O6'6.1 (8)N5—C12—N4—C1643.5 (3)
N4—C12—C13—O6'131.5 (8)C13—C12—N4—C1683.7 (2)
C8—C12—C13—O6'114.0 (8)C8—C12—N4—C16154.36 (19)
O5—C13—O6—C141.2 (8)N6—C16—N4—C688.8 (3)
O6'—C13—O6—C14106 (2)N6—C16—N4—C1252.5 (3)
C12—C13—O6—C14171.1 (4)O2—C7—N5—C12168.0 (2)
C15—C14—O6—C1398.7 (10)N3—C7—N5—C1216.0 (3)
O5—C13—O6'—C14'17.1 (18)O2—C7—N5—C1726.8 (3)
O6—C13—O6'—C14'75 (2)N3—C7—N5—C17157.2 (2)
C12—C13—O6'—C14'176.5 (13)N4—C12—N5—C7101.4 (2)
C15'—C14'—O6'—C13125 (2)C13—C12—N5—C7135.0 (2)
C2—C3—N1—C5177.4 (3)C8—C12—N5—C79.0 (2)
C1—C3—N1—C561.0 (4)N4—C12—N5—C1742.0 (3)
C2—C3—N1—C451.8 (4)C13—C12—N5—C1781.5 (3)
C1—C3—N1—C4168.3 (3)C8—C12—N5—C17152.5 (2)
N3—C5—N1—C382.0 (3)N6—C17—N5—C790.0 (3)
N3—C5—N1—C451.6 (3)N6—C17—N5—C1249.2 (3)
N2—C4—N1—C382.3 (3)N4—C16—N6—C1755.8 (3)
N2—C4—N1—C550.4 (3)N4—C16—N6—C1876.6 (3)
O1—C6—N2—C8170.8 (2)N5—C17—N6—C1654.1 (3)
N4—C6—N2—C812.9 (2)N5—C17—N6—C1877.6 (3)
O1—C6—N2—C425.5 (3)C20—C18—N6—C1655.6 (3)
N4—C6—N2—C4158.28 (19)C19—C18—N6—C16176.5 (2)
N3—C8—N2—C6103.6 (2)C20—C18—N6—C17175.4 (3)
C9—C8—N2—C6132.9 (2)C19—C18—N6—C1754.5 (3)
C12—C8—N2—C67.2 (2)O3—C9—O4—C104.9 (5)
N3—C8—N2—C444.7 (3)C8—C9—O4—C10176.9 (3)
C9—C8—N2—C478.8 (3)C11—C10—O4—C9141.0 (6)
C12—C8—N2—C4155.6 (2)C11'—C10—O4—C968.5 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C17—H17A···O20.972.592.923 (3)100
C14—H14A···O50.972.342.700 (9)101
C10—H10A···O30.972.322.677 (5)101
C5—H5A···O2i0.972.523.205 (3)128
Symmetry code: (i) x+3/2, y+1/2, z+1/2.
 

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