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In the title compound, C18H26N4O4, the bridgehead N atom is located toward the inside of the cage and the displacement from the aromatic ring is 4.2110 (13) Å. The three C atoms adjacent to the bridgehead N atom are disordered with roughly equal occupancy between two sets of positions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019183/ob6084sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019183/ob6084Isup2.hkl
Contains datablock I

CCDC reference: 177219

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.116
  • Data-to-parameter ratio = 14.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT; data reduction: SHELXTL (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: PLATON (Spek, 2001).

3,5,8,19-Tetraaza-2,9,18-trione-[55,13][11]metacyclophane monohydrate top
Crystal data top
C18H24N4O3·H2OF(000) = 776
Mr = 362.43Dx = 1.345 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 11459 reflections
a = 9.3436 (8) Åθ = 2.1–28.3°
b = 13.4554 (12) ŵ = 0.10 mm1
c = 14.2888 (12) ÅT = 298 K
β = 94.748 (2)°Plate, colorless
V = 1790.3 (3) Å30.5 × 0.35 × 0.25 mm
Z = 4
Data collection top
CCD area detector
diffractometer
2794 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.064
Graphite monochromatorθmax = 28.3°, θmin = 2.1°
φ and ω scansh = 128
11459 measured reflectionsk = 1717
4316 independent reflectionsl = 1819
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0559P)2 + 0.0871P]
where P = (Fo2 + 2Fc2)/3
4316 reflections(Δ/σ)max = 0.002
295 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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)
O10.30412 (14)1.00794 (9)0.07705 (8)0.0657 (5)
O20.55060 (12)0.71597 (10)0.38548 (7)0.0586 (4)
O30.10149 (13)0.51426 (10)0.14048 (9)0.0628 (5)
N0.11802 (11)0.81686 (9)0.17809 (8)0.0352 (4)
N10.28539 (15)0.91248 (11)0.04910 (9)0.0460 (4)
N20.37479 (13)0.73510 (11)0.27019 (9)0.0449 (5)
N30.05146 (14)0.64347 (10)0.04433 (9)0.0416 (4)
C10.1412 (3)0.9259 (2)0.1779 (2)0.0442 (10)0.527 (3)
C20.1199 (3)0.7762 (3)0.26965 (19)0.0457 (10)0.527 (3)
C30.0214 (3)0.7968 (2)0.1207 (2)0.0430 (10)0.527 (3)
C40.17556 (18)0.96932 (13)0.09021 (13)0.0517 (5)
C50.26724 (17)0.77481 (13)0.32671 (10)0.0476 (5)
C60.05292 (15)0.68939 (13)0.09992 (11)0.0448 (5)
C70.33745 (16)0.93241 (12)0.03227 (10)0.0419 (5)
C80.50883 (16)0.71157 (11)0.30184 (10)0.0397 (5)
C90.12280 (15)0.56057 (11)0.06912 (10)0.0394 (5)
C100.44457 (17)0.85959 (12)0.06695 (10)0.0452 (5)
C110.61011 (15)0.67943 (13)0.22977 (10)0.0440 (5)
C120.23802 (16)0.52953 (12)0.00620 (10)0.0427 (5)
C130.45930 (15)0.76359 (11)0.01214 (9)0.0365 (4)
C140.54648 (15)0.75839 (12)0.07174 (10)0.0381 (4)
C150.54160 (13)0.67648 (11)0.13075 (10)0.0365 (4)
C160.45057 (15)0.59806 (12)0.10344 (10)0.0375 (4)
C170.36057 (14)0.60276 (11)0.02132 (9)0.0356 (4)
C180.36816 (15)0.68439 (11)0.03682 (10)0.0366 (4)
C1P0.0615 (4)0.9004 (3)0.1263 (3)0.0456 (11)0.473 (3)
C2P0.1752 (3)0.8470 (3)0.2763 (2)0.0424 (10)0.473 (3)
C3P0.0087 (3)0.7392 (3)0.1899 (2)0.0412 (10)0.473 (3)
O1W0.3533 (2)1.05659 (15)0.26470 (12)0.0974 (8)
H1A0.055000.957800.196800.0530*0.527 (3)
H1B0.218500.941500.225200.0530*0.527 (3)
H2N0.3493 (19)0.7325 (14)0.2103 (13)0.060 (5)*
H3A0.099100.823900.153800.0520*0.527 (3)
H3B0.020500.832200.061600.0520*0.527 (3)
H3N0.0706 (19)0.6719 (14)0.0053 (14)0.059 (6)*
H1N0.3033 (19)0.8557 (15)0.0727 (13)0.063 (6)*
H2A0.084300.708500.264500.0550*0.527 (3)
H2B0.053600.813800.304600.0550*0.527 (3)
H5B0.261900.734200.382400.0570*0.527 (3)
H6A0.055000.653500.158700.0540*0.527 (3)
H6B0.147300.684000.066600.0540*0.527 (3)
H10A0.416200.844000.132100.0540*
H10B0.537800.891600.064700.0540*
H11A0.691000.724800.232400.0530*
H11B0.647100.613800.246400.0530*
H12A0.271200.462900.022100.0510*
H12B0.199900.530100.059000.0510*
H140.6043 (17)0.8165 (12)0.0905 (11)0.044 (4)*
H160.4443 (15)0.5404 (12)0.1449 (10)0.038 (4)*
H180.3049 (16)0.6893 (11)0.0925 (11)0.041 (4)*
H4A0.208701.037000.101000.0620*0.527 (3)
H4B0.089900.971400.047000.0620*0.527 (3)
H5A0.293500.841800.346500.0570*0.527 (3)
H4PA0.130501.014300.043600.0620*0.473 (3)
H4PB0.218901.008800.141800.0620*0.473 (3)
H5PA0.314400.806000.382200.0570*0.473 (3)
H5PB0.208800.720700.347200.0570*0.473 (3)
H6PA0.120800.639000.116100.0540*0.473 (3)
H6PB0.105800.738700.061500.0540*0.473 (3)
H11P0.002600.938700.165900.0550*0.473 (3)
H12P0.000200.876800.073000.0550*0.473 (3)
H21P0.228400.908500.272300.0510*0.473 (3)
H22P0.094200.860400.312700.0510*0.473 (3)
H31P0.069700.768900.220500.0500*0.473 (3)
H32P0.051300.688400.231500.0500*0.473 (3)
H1W0.346 (3)1.040 (2)0.208 (2)0.128 (11)*
H2W0.447 (5)1.038 (4)0.274 (3)0.21 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0837 (9)0.0546 (8)0.0609 (8)0.0104 (6)0.0190 (7)0.0241 (6)
O20.0577 (7)0.0788 (9)0.0364 (6)0.0024 (6)0.0132 (5)0.0043 (5)
O30.0653 (8)0.0652 (9)0.0595 (7)0.0076 (6)0.0151 (6)0.0227 (6)
N0.0314 (6)0.0373 (7)0.0370 (6)0.0019 (5)0.0035 (5)0.0007 (5)
N10.0525 (8)0.0406 (8)0.0466 (7)0.0089 (6)0.0147 (6)0.0100 (6)
N20.0380 (7)0.0668 (10)0.0292 (6)0.0056 (6)0.0013 (5)0.0047 (6)
N30.0437 (7)0.0427 (8)0.0381 (7)0.0018 (6)0.0010 (6)0.0016 (6)
C10.0463 (17)0.0406 (18)0.0476 (17)0.0002 (13)0.0159 (15)0.0104 (13)
C20.0443 (16)0.057 (2)0.0372 (15)0.0008 (15)0.0115 (12)0.0021 (14)
C30.0336 (14)0.0476 (19)0.0473 (16)0.0026 (12)0.0002 (12)0.0006 (14)
C40.0515 (9)0.0389 (9)0.0666 (10)0.0057 (7)0.0160 (8)0.0044 (8)
C50.0452 (8)0.0643 (11)0.0331 (7)0.0002 (7)0.0029 (6)0.0076 (7)
C60.0339 (7)0.0498 (10)0.0500 (9)0.0036 (7)0.0001 (6)0.0035 (7)
C70.0443 (8)0.0411 (9)0.0402 (8)0.0076 (7)0.0027 (6)0.0053 (7)
C80.0398 (8)0.0419 (9)0.0357 (7)0.0044 (6)0.0068 (6)0.0002 (6)
C90.0372 (7)0.0398 (9)0.0398 (8)0.0089 (6)0.0053 (6)0.0019 (7)
C100.0509 (9)0.0491 (10)0.0369 (8)0.0063 (7)0.0106 (7)0.0031 (7)
C110.0307 (7)0.0566 (10)0.0432 (8)0.0023 (7)0.0056 (6)0.0007 (7)
C120.0464 (8)0.0386 (9)0.0423 (8)0.0052 (7)0.0011 (6)0.0077 (7)
C130.0344 (7)0.0412 (9)0.0350 (7)0.0002 (6)0.0095 (6)0.0014 (6)
C140.0313 (7)0.0430 (9)0.0407 (7)0.0040 (6)0.0065 (6)0.0043 (7)
C150.0268 (6)0.0455 (9)0.0372 (7)0.0037 (6)0.0022 (5)0.0033 (6)
C160.0394 (8)0.0356 (8)0.0375 (7)0.0031 (6)0.0023 (6)0.0009 (6)
C170.0351 (7)0.0360 (8)0.0360 (7)0.0010 (6)0.0047 (6)0.0093 (6)
C180.0350 (7)0.0444 (9)0.0303 (7)0.0007 (6)0.0029 (6)0.0034 (6)
C1P0.0421 (19)0.045 (2)0.0498 (19)0.0079 (15)0.0040 (16)0.0041 (16)
C2P0.0383 (17)0.048 (2)0.0412 (17)0.0008 (15)0.0055 (13)0.0125 (15)
C3P0.0359 (15)0.048 (2)0.0406 (17)0.0072 (14)0.0082 (13)0.0013 (15)
O1W0.1187 (15)0.1181 (16)0.0557 (9)0.0230 (11)0.0097 (9)0.0136 (9)
Geometric parameters (Å, º) top
O1—C71.227 (2)C16—C171.3873 (19)
O2—C81.2276 (17)C17—C181.383 (2)
O3—C91.2252 (19)C1—H1B0.9704
O1W—H1W0.85 (3)C1—H1A0.9705
O1W—H2W0.93 (5)C1P—H11P0.9696
N—C31.505 (3)C1P—H12P0.9698
N—C11.483 (3)C2—H2B0.9697
N—C21.417 (3)C2—H2A0.9705
N—C3P1.481 (4)C2P—H21P0.9694
N—C2P1.515 (3)C2P—H22P0.9700
N—C1P1.423 (4)C3—H3B0.9702
N1—C41.443 (2)C3—H3A0.9698
N1—C71.324 (2)C3P—H31P0.9698
N2—C81.3340 (19)C3P—H32P0.9694
N2—C51.443 (2)C4—H4B0.9699
N3—C61.446 (2)C4—H4PA0.9699
N3—C91.332 (2)C4—H4A0.9701
N1—H1N0.85 (2)C4—H4PB0.9696
N2—H2N0.870 (18)C5—H5A0.9701
N3—H3N0.84 (2)C5—H5B0.9700
C1—C41.443 (3)C5—H5PA0.9701
C1P—C41.534 (4)C5—H5PB0.9698
C2—C51.541 (3)C6—H6A0.9704
C2P—C51.449 (4)C6—H6B0.9696
C3—C61.500 (3)C6—H6PA0.9694
C3P—C61.520 (3)C6—H6PB0.9700
C7—C101.513 (2)C10—H10A0.9695
C8—C111.518 (2)C10—H10B0.9699
C9—C121.517 (2)C11—H11B0.9706
C10—C131.511 (2)C11—H11A0.9699
C11—C151.504 (2)C12—H12A0.9695
C12—C171.513 (2)C12—H12B0.9695
C13—C181.391 (2)C14—H140.975 (16)
C13—C141.3940 (19)C16—H160.981 (16)
C14—C151.391 (2)C18—H180.953 (15)
C15—C161.391 (2)
O1···O1W2.834 (2)H2A···C62.5964
O1W···O3i2.940 (2)H2A···H10Aiv2.3522
O1W···O12.834 (2)H2A···H6A2.0497
O2···C18ii3.3599 (19)H2A···C10iv2.9774
O2···N3ii2.9540 (18)H2B···H1A2.4760
O3···C3P3.242 (4)H2B···H3A2.4876
O3···C2Piii3.228 (4)H2B···C13iv3.0165
O3···O1Wiv2.940 (2)H2B···C18iv2.9643
O1···H1W1.99 (3)H2N···C142.835 (18)
O1···H14v2.525 (16)H2N···C152.330 (18)
O1···H4B2.8244H2N···C162.596 (19)
O1···H4PA2.4645H2N···H1N2.58 (3)
O1···H4A2.7921H2N···N2.451 (18)
O1···H10Bv2.7597H2W···O3i2.09 (5)
O1W···H12Bvi2.5520H5PA···O22.5146
O2···H5PA2.5146H3A···H2B2.4876
O2···H5B2.7054H3A···H1A2.3559
O2···H3Nii2.17 (2)H3B···C42.6083
O2···H3Bii2.7333H3B···O2vii2.7333
O2···H18ii2.692 (15)H3B···H3N2.5348
O3···H6PA2.6707H3B···H4B2.1567
O3···H32P2.7391H3N···O2vii2.168 (19)
O3···H5Aiii2.5203H3N···H3B2.5348
O3···H2Wiv2.09 (5)H3N···H12B2.4171
O3···H1Biii2.6337H3N···C172.860 (18)
O3···H21Piii2.4035H3N···C182.858 (18)
O3···H6A2.4039H5PB···C3P2.8131
N···N12.8240 (18)H5PB···C10iv3.0444
N···N22.8593 (17)H5PB···H32P2.1645
N···N33.0473 (18)H5PB···H10Biv2.5988
N1···C143.198 (2)H4A···O12.7921
N1···C183.418 (2)H4B···O12.8244
N1···N2.8240 (18)H4B···H4Bxii2.2012
N2···N2.8593 (17)H4B···C32.8091
N2···C143.3861 (19)H4B···H3B2.1567
N2···C163.140 (2)H6PA···O32.6707
N3···N3.0473 (18)H6PA···H12Bix2.5078
N3···C183.3124 (19)H6PA···C12ix3.0131
N3···O2vii2.9540 (18)H5A···O3viii2.5203
N···H1N2.443 (18)H5A···H12Aviii2.5949
N···H2N2.451 (18)H5A···H1B2.2569
C2···C10iv3.479 (4)H5A···C12.9226
C2P···O3viii3.228 (4)H5B···O22.7054
C3P···O33.242 (4)H6PB···H12P2.1039
C7···C7v3.595 (2)H6PB···C1P2.7920
C9···C9ix3.328 (2)H6A···H2A2.0497
C10···C2i3.479 (4)H6A···C22.7351
C14···N23.3861 (19)H6A···O32.4039
C14···N13.198 (2)H6B···H12Aix2.5711
C16···N23.140 (2)H6B···C14x3.0378
C18···N33.3124 (19)H10A···H182.4149
C18···N13.418 (2)H10A···C2i2.9413
C18···O2vii3.3599 (19)H10A···H2Ai2.3522
C1···H5A2.9226H10A···H32Pi2.4473
C1P···H6PB2.7920H10A···C3Pi2.9720
C2···H10Aiv2.9413H10B···H5PBi2.5988
C2···H6A2.7351H10B···C7v2.9358
C2P···H4PB2.9546H10B···O1v2.7597
C2P···H16viii3.081 (16)H10B···H142.4692
C3···H4B2.8091H11A···H142.4531
C3P···H11Ax3.0849H11A···H31Pxi2.3331
C3P···H5PB2.8131H11A···C3Pxi3.0849
C3P···H10Aiv2.9720H11B···H162.4929
C4···H21P2.7332H11P···H22P2.4383
C4···H3B2.6083H11P···H31P2.5243
C5···H32P2.6113H11P···H21P2.5292
C5···H1B2.6893H12A···H162.5124
C6···H2A2.5964H12A···H6Bix2.5711
C6···H12P2.6040H12A···H5Aiii2.5949
C7···H1W2.91 (3)H12B···O1Wxiii2.5520
C7···H10Bv2.9358H12B···H6PAix2.5078
C9···H32P3.0074H12B···H3N2.4171
C10···H2Ai2.9774H12B···H182.4203
C10···H5PBi3.0444H12P···C62.6040
C12···H6PAix3.0131H12P···H6PB2.1039
C13···H2Bi3.0165H12P···H4PAxii2.4636
C13···H1N2.329 (19)H14···H11A2.4531
C14···H6Bxi3.0378H14···O1v2.525 (16)
C14···H2N2.835 (18)H14···H1Wv2.58 (3)
C14···H1N2.623 (19)H14···H10B2.4692
C15···H2N2.330 (18)H16···H22Piii2.5295
C16···H2N2.596 (19)H16···H12A2.5124
C17···H3N2.860 (18)H16···H1Aiii2.5197
C18···H3N2.858 (18)H16···H11B2.4929
C18···H2Bi2.9643H16···C2Piii3.081 (16)
C18···H1N2.88 (2)H18···H12B2.4203
H4PA···H12Pxii2.4636H18···O2vii2.692 (15)
H4PA···O12.4645H18···H10A2.4149
H1A···H2B2.4760H21P···H11P2.5292
H1A···H3A2.3559H21P···C42.7332
H1A···H16viii2.5197H21P···H4PB2.2976
H1B···C52.6893H21P···O3viii2.4035
H1B···O3viii2.6337H22P···H16viii2.5295
H1B···H5A2.2569H22P···H11P2.4383
H1N···C132.329 (19)H22P···H31P2.2940
H1N···N2.443 (18)H31P···H11Ax2.3331
H1N···C182.88 (2)H31P···H11P2.5243
H1N···H2N2.58 (3)H31P···H22P2.2940
H1N···C142.623 (19)H32P···O32.7391
H1W···C72.91 (3)H32P···C52.6113
H1W···H14v2.58 (3)H32P···C93.0074
H1W···O11.99 (3)H32P···H5PB2.1645
H4PB···H21P2.2976H32P···H10Aiv2.4473
H4PB···C2P2.9546
H1W—O1W—H2W103 (3)C5—C2—H2B108.34
C1—N—C2113.1 (2)N—C2—H2B108.33
C1—N—C3107.24 (17)H21P—C2P—H22P107.43
C1P—N—C2P110.9 (2)C5—C2P—H21P108.39
C1P—N—C3P112.8 (2)C5—C2P—H22P108.38
C2—N—C3112.20 (18)N—C2P—H22P108.39
C2P—N—C3P106.09 (18)N—C2P—H21P108.49
C4—N1—C7125.12 (14)C6—C3—H3B108.45
C5—N2—C8125.17 (13)H3A—C3—H3B107.50
C6—N3—C9123.84 (13)N—C3—H3A108.42
C4—N1—H1N116.1 (12)C6—C3—H3A108.43
C7—N1—H1N117.2 (12)N—C3—H3B108.46
C8—N2—H2N119.8 (12)C6—C3P—H32P108.38
C5—N2—H2N114.8 (12)C6—C3P—H31P108.40
C6—N3—H3N118.1 (13)H31P—C3P—H32P107.53
C9—N3—H3N118.0 (13)N—C3P—H31P108.33
N—C1—C4116.4 (2)N—C3P—H32P108.38
N—C1P—C4114.5 (3)C1—C4—H4A109.46
N—C2—C5115.8 (2)N1—C4—H4A109.50
N—C2P—C5115.5 (3)N1—C4—H4B109.47
N—C3—C6115.32 (19)N1—C4—H4PA109.52
N—C3P—C6115.5 (2)C1—C4—H4B109.47
N1—C4—C1110.84 (17)H4A—C4—H4B108.05
N1—C4—C1P110.71 (19)C1P—C4—H4PA109.51
N2—C5—C2P112.47 (16)C1P—C4—H4PB109.49
N2—C5—C2109.97 (15)H4PA—C4—H4PB108.08
N3—C6—C3112.96 (16)N1—C4—H4PB109.48
N3—C6—C3P115.30 (15)N2—C5—H5B109.64
O1—C7—C10120.77 (13)N2—C5—H5PA109.11
N1—C7—C10117.22 (14)N2—C5—H5A109.64
O1—C7—N1121.98 (15)C2—C5—H5A109.65
O2—C8—C11120.56 (13)C2—C5—H5B109.67
O2—C8—N2122.18 (14)H5A—C5—H5B108.25
N2—C8—C11117.27 (12)C2P—C5—H5PA109.09
N3—C9—C12115.90 (13)C2P—C5—H5PB109.12
O3—C9—C12121.69 (14)H5PA—C5—H5PB107.88
O3—C9—N3122.34 (14)N2—C5—H5PB109.06
C7—C10—C13114.72 (12)N3—C6—H6A108.99
C8—C11—C15113.89 (12)N3—C6—H6B109.00
C9—C12—C17107.57 (12)N3—C6—H6PA108.45
C14—C13—C18118.77 (13)N3—C6—H6PB108.45
C10—C13—C18119.73 (12)C3—C6—H6A109.02
C10—C13—C14120.68 (13)C3—C6—H6B108.97
C13—C14—C15120.99 (14)H6A—C6—H6B107.77
C14—C15—C16118.76 (13)C3P—C6—H6PA108.43
C11—C15—C16119.12 (13)C3P—C6—H6PB108.46
C11—C15—C14121.10 (13)H6PA—C6—H6PB107.50
C15—C16—C17121.10 (14)C7—C10—H10A108.59
C12—C17—C16119.33 (13)C7—C10—H10B108.55
C12—C17—C18120.50 (12)C13—C10—H10A108.58
C16—C17—C18119.13 (13)C13—C10—H10B108.63
C13—C18—C17121.13 (13)H10A—C10—H10B107.54
C10—C13—C16171.00 (10)C8—C11—H11B108.81
C11—C15—C18168.92 (10)C15—C11—H11A108.82
C12—C17—C14167.97 (10)C15—C11—H11B108.75
N—C1—H1B108.25H11A—C11—H11B107.62
C4—C1—H1A108.18C8—C11—H11A108.78
N—C1—H1A108.20C9—C12—H12A110.15
H1A—C1—H1B107.31C17—C12—H12A110.20
C4—C1—H1B108.12C17—C12—H12B110.22
C4—C1P—H12P108.56C9—C12—H12B110.18
H11P—C1P—H12P107.64H12A—C12—H12B108.51
C4—C1P—H11P108.58C15—C14—H14120.9 (9)
N—C1P—H11P108.69C13—C14—H14117.8 (9)
N—C1P—H12P108.70C15—C16—H16119.8 (9)
H2A—C2—H2B107.41C17—C16—H16119.0 (9)
N—C2—H2A108.33C13—C18—H18118.9 (9)
C5—C2—H2A108.32C17—C18—H18119.8 (9)
C2—N—C1—C4165.4 (2)N—C1—C4—N146.8 (3)
C3—N—C1—C470.3 (2)N—C2—C5—N248.0 (3)
C1—N—C2—C570.1 (3)N—C3—C6—N362.6 (2)
C3—N—C2—C5168.4 (2)N1—C7—C10—C1310.2 (2)
C1—N—C3—C6170.93 (19)O1—C7—C10—C13171.80 (14)
C2—N—C3—C664.2 (3)N2—C8—C11—C151.4 (2)
C7—N1—C4—C1178.50 (18)O2—C8—C11—C15179.11 (14)
C4—N1—C7—O16.4 (3)N3—C9—C12—C1770.72 (16)
C4—N1—C7—C10175.59 (14)O3—C9—C12—C17106.26 (16)
C8—N2—C5—C2170.7 (2)C7—C10—C13—C1482.12 (17)
C5—N2—C8—O24.8 (3)C7—C10—C13—C1887.39 (16)
C5—N2—C8—C11174.66 (15)C8—C11—C15—C1492.19 (16)
C9—N3—C6—C3126.16 (18)C8—C11—C15—C1676.12 (18)
C6—N3—C9—O32.6 (2)C9—C12—C17—C1674.19 (17)
C6—N3—C9—C12174.34 (13)C9—C12—C17—C1894.07 (15)
C1—N—C2—H2A168.07C18—C13—C14—C150.9 (2)
C1—N—C2—H2B51.85C10—C13—C14—C15168.67 (13)
C3—N—C2—H2A46.57C10—C13—C18—C17168.07 (13)
C3—N—C2—H2B69.65C14—C13—C18—C171.6 (2)
C1—N—C3—H3A67.32C13—C14—C15—C11166.64 (13)
C1—N—C3—H3B49.12C13—C14—C15—C161.7 (2)
C2—N—C3—H3A57.50C14—C15—C16—C173.2 (2)
C2—N—C3—H3B173.94C11—C15—C16—C17165.38 (13)
C3—N—C1—H1B167.68C15—C16—C17—C12164.54 (13)
C2—N—C1—H1A72.56C15—C16—C17—C183.9 (2)
C2—N—C1—H1B43.42C16—C17—C18—C133.1 (2)
C3—N—C1—H1A51.69C12—C17—C18—C13165.20 (13)
Symmetry codes: (i) x+1/2, y+3/2, z1/2; (ii) x+1/2, y+3/2, z+1/2; (iii) x+1/2, y1/2, z+1/2; (iv) x1/2, y+3/2, z+1/2; (v) x+1, y+2, z; (vi) x+1/2, y+1/2, z1/2; (vii) x1/2, y+3/2, z1/2; (viii) x+1/2, y+1/2, z+1/2; (ix) x, y+1, z; (x) x1, y, z; (xi) x+1, y, z; (xii) x, y+2, z; (xiii) x+1/2, y1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···N0.85 (2)2.443 (18)2.8240 (18)108.2 (14)
O1W—H1W···O10.85 (3)1.99 (3)2.834 (2)173 (3)
N2—H2N···N0.870 (18)2.451 (18)2.8593 (17)109.4 (14)
O1W—H2W···O3i0.93 (5)2.09 (5)2.940 (2)151 (4)
N3—H3N···O2vii0.84 (2)2.168 (19)2.9540 (18)156.3 (17)
C5—H5A···O3viii0.972.523.465 (2)165
C6—H6A···O30.972.402.799 (2)104
C12—H12B···O1Wxiii0.972.553.504 (2)167
C14—H14···O1v0.975 (16)2.525 (16)3.438 (2)155.9 (13)
Symmetry codes: (i) x+1/2, y+3/2, z1/2; (v) x+1, y+2, z; (vii) x1/2, y+3/2, z1/2; (viii) x+1/2, y+1/2, z+1/2; (xiii) x+1/2, y1/2, z1/2.
 

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