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The cation of the title compound, H4tptn4+·4ClO4·H2O, where H4tptn4+ is N,N,N′,N′-tetrakis(2-pyridinio­methyl)-1,3-di­amino­propane (C27H34N64+), contains an intramolecular N—H...N hydrogen bond, and the average ring angle at the N atoms in the pyridinium rings is 123.6 (1)°. Intermolecular N—H...O and O—H...O hydrogen bonds are also found in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011961/ob6371sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011961/ob6371Isup2.hkl
Contains datablock I

CCDC reference: 245272

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.066
  • wR factor = 0.183
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART-W2K/NT (Bruker, 2003); cell refinement: SAINT-W2K/NT (Bruker, 2003); data reduction: SAINT-W2K/NT; program(s) used to solve structure: SHELXTL-NT (Bruker, 2003); program(s) used to refine structure: SHELXTL-NT; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL-NT.

N,N,N',N'-Tetrakis(2-pyridiniomethyl)-1,3-diaminopropane tetraperchlorate hydrate top
Crystal data top
C27H34N64+·4ClO4·H2OZ = 2
Mr = 858.42F(000) = 888
Triclinic, P1Dx = 1.577 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.6648 (6) ÅCell parameters from 8505 reflections
b = 12.3882 (6) Åθ = 2.4–27.9°
c = 12.5333 (6) ŵ = 0.41 mm1
α = 92.168 (1)°T = 173 K
β = 91.050 (1)°Plate, colourless
γ = 92.252 (1)°0.50 × 0.40 × 0.25 mm
V = 1808.09 (15) Å3
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
8519 independent reflections
Radiation source: fine-focus sealed tube7487 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 8.366 pixels mm-1θmax = 27.9°, θmin = 1.6°
φ and ω scansh = 1513
Absorption correction: multi-scan
(SADABS; Scheldrick, 1996)
k = 1615
Tmin = 0.821, Tmax = 0.904l = 1616
13190 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.183 w = 1/[σ2(Fo2) + (0.0956P)2 + 2.858P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
8519 reflectionsΔρmax = 1.25 e Å3
512 parametersΔρmin = 1.19 e Å3
0 restraintsExtinction correction: SHELXTL-NT, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0043 (10)
Special details top

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

7.4974 (0.0104) x - 9.0912 (0.0099) y + 3.8244 (0.0144) z = 3.9411 (0.0113)

* -0.0021 (0.0019) N6 * -0.0068 (0.0018) C23 * 0.0095 (0.0020) C24 * -0.0034 (0.0021) C25 * -0.0054 (0.0021) C26 * 0.0083 (0.0021) C27

Rms deviation of fitted atoms = 0.0065

2.0958 (0.0146) x - 8.0267 (0.0125) y + 9.6089 (0.0106) z = 3.2947 (0.0080)

Angle to previous plane (with approximate e.s.d.) = 38.14 (0.12)

* 0.0090 (0.0020) N5 * 0.0018 (0.0019) C17 * -0.0101 (0.0021) C18 * 0.0077 (0.0024) C19 * 0.0028 (0.0025) C20 * -0.0112 (0.0023) C21

Rms deviation of fitted atoms = 0.0080

4.3281 (0.0123) x - 6.5188 (0.0124) y - 9.5383 (0.0095) z = 1.0154 (0.0100)

Angle to previous plane (with approximate e.s.d.) = 79.47 (0.08)

* -0.0021 (0.0018) N4 * 0.0023 (0.0018) C11 * 0.0013 (0.0020) C12 * -0.0050 (0.0021) C13 * 0.0052 (0.0021) C14 * -0.0017 (0.0020) C15

Rms deviation of fitted atoms = 0.0033

3.0708 (0.0158) x - 4.8544 (0.0164) y - 10.9697 (0.0084) z = 0.2415 (0.0054)

Angle to previous plane (with approximate e.s.d.) = 11.62 (0.17)

* 0.0012 (0.0019) N3 * 0.0095 (0.0021) C5 * -0.0108 (0.0027) C6 * 0.0017 (0.0028) C7 * 0.0089 (0.0025) C8 * -0.0105 (0.0021) C9

Rms deviation of fitted atoms = 0.0082

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
N10.40662 (19)0.20289 (17)0.02173 (16)0.0225 (4)
N20.37651 (19)0.21089 (18)0.42106 (16)0.0237 (4)
N30.2165 (2)0.27265 (19)0.08218 (18)0.0275 (5)
N40.6085 (2)0.31537 (19)0.04565 (18)0.0277 (5)
N50.1549 (2)0.1608 (2)0.4444 (2)0.0311 (5)
N60.5972 (2)0.2981 (2)0.56764 (18)0.0286 (5)
C10.3905 (2)0.2653 (2)0.12303 (19)0.0233 (5)
C20.3988 (3)0.2012 (2)0.2244 (2)0.0334 (6)
C30.3783 (2)0.2731 (2)0.32284 (19)0.0246 (5)
C40.3130 (2)0.1234 (2)0.0026 (2)0.0282 (5)
C50.2069 (2)0.1743 (2)0.0421 (2)0.0295 (5)
C60.1004 (3)0.1214 (3)0.0467 (3)0.0457 (8)
C70.0090 (3)0.1693 (3)0.0946 (3)0.0529 (9)
C80.0233 (3)0.2705 (3)0.1360 (3)0.0426 (7)
C90.1287 (3)0.3223 (3)0.1276 (2)0.0347 (6)
C100.5167 (2)0.1504 (2)0.0177 (2)0.0256 (5)
C110.6172 (2)0.2300 (2)0.01619 (19)0.0247 (5)
C120.7192 (2)0.2174 (2)0.0712 (2)0.0314 (6)
C130.8090 (3)0.2923 (3)0.0614 (3)0.0375 (6)
C140.7972 (3)0.3787 (3)0.0041 (3)0.0372 (6)
C150.6941 (3)0.3891 (2)0.0573 (2)0.0329 (6)
C160.3213 (2)0.2702 (2)0.5074 (2)0.0273 (5)
C170.1938 (2)0.2452 (2)0.5057 (2)0.0268 (5)
C180.1168 (3)0.3006 (3)0.5675 (2)0.0352 (6)
C190.0023 (3)0.2654 (3)0.5649 (3)0.0440 (8)
C200.0343 (3)0.1777 (3)0.4991 (3)0.0471 (8)
C210.0438 (3)0.1263 (3)0.4376 (3)0.0431 (7)
C220.4858 (2)0.1646 (2)0.4520 (2)0.0259 (5)
C230.5839 (2)0.2468 (2)0.4706 (2)0.0255 (5)
C240.6603 (2)0.2752 (2)0.3928 (2)0.0314 (6)
C250.7452 (3)0.3553 (3)0.4135 (2)0.0368 (6)
C260.7547 (3)0.4057 (3)0.5140 (3)0.0359 (6)
C270.6794 (2)0.3745 (3)0.5909 (2)0.0340 (6)
H3N0.283 (3)0.307 (3)0.083 (3)0.040 (10)*
H4N0.544 (4)0.323 (3)0.081 (3)0.041 (10)*
H5N0.203 (4)0.129 (3)0.416 (3)0.039 (10)*
H6N0.550 (3)0.272 (3)0.617 (3)0.037 (9)*
H1A0.31410.29740.12010.028*
H1B0.44880.32560.12820.028*
H2A0.34110.14030.22050.040*
H2B0.47580.17080.23000.040*
H3A0.43980.33050.32970.030*
H3B0.30420.30830.31410.030*
H4A0.29500.08380.06250.034*
H4B0.33820.07040.05760.034*
H60.09020.05240.01690.055*
H70.06410.13250.09910.063*
H80.03910.30350.16980.051*
H90.14000.39290.15380.042*
H10A0.51770.10230.04710.031*
H10B0.52460.10510.08060.031*
H120.72760.15760.11550.038*
H130.87900.28450.09970.045*
H140.85890.42980.01220.045*
H150.68370.44840.10200.040*
H16A0.33600.34870.49990.033*
H16B0.35460.25030.57680.033*
H180.14180.36180.61100.042*
H190.05120.30150.60840.053*
H200.11270.15370.49680.057*
H210.02040.06710.39080.052*
H22A0.50720.11190.39520.031*
H22B0.47440.12470.51810.031*
H240.65470.23960.32430.038*
H250.79650.37550.35900.044*
H260.81230.46080.52940.043*
H270.68550.40700.66070.041*
O10.4856 (2)0.21659 (18)0.74620 (16)0.0314 (4)
H1010.520 (4)0.165 (4)0.750 (4)0.057 (13)*
H1020.422 (4)0.204 (3)0.748 (3)0.039 (11)*
Cl10.40441 (5)0.47317 (5)0.79135 (5)0.02524 (16)
Cl20.26320 (6)0.01407 (5)0.69972 (5)0.03152 (17)
Cl30.25709 (6)0.91307 (6)0.26587 (6)0.03417 (18)
Cl40.06659 (6)0.43105 (7)0.23417 (6)0.0398 (2)
O110.40262 (18)0.42509 (16)0.89601 (16)0.0326 (4)
O120.3695 (2)0.58222 (16)0.80275 (17)0.0358 (5)
O210.2543 (2)0.12858 (18)0.72360 (18)0.0390 (5)
O140.3273 (2)0.41089 (19)0.72085 (18)0.0421 (5)
O130.5195 (2)0.47124 (19)0.7529 (2)0.0438 (5)
O230.3638 (2)0.0223 (2)0.75433 (19)0.0448 (6)
O220.2762 (3)0.0046 (3)0.5877 (2)0.0670 (9)
O240.1657 (3)0.0449 (3)0.7391 (3)0.0698 (9)
O310.2141 (3)0.8049 (2)0.2723 (4)0.0904 (13)
O340.3340 (7)0.9377 (3)0.3485 (4)0.157 (3)
O330.3170 (6)0.9211 (3)0.1752 (3)0.153 (3)
O420.0387 (5)0.4733 (5)0.2552 (6)0.151 (3)
O430.0608 (6)0.4127 (6)0.1248 (4)0.172 (3)
O320.1726 (3)0.9901 (3)0.2667 (6)0.149 (3)
O410.1612 (5)0.4995 (7)0.2472 (4)0.173 (3)
O440.0727 (6)0.3407 (7)0.2879 (8)0.225 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0272 (10)0.0212 (10)0.0189 (9)0.0002 (8)0.0003 (8)0.0004 (7)
N20.0265 (10)0.0276 (11)0.0173 (9)0.0020 (8)0.0007 (8)0.0013 (8)
N30.0268 (11)0.0305 (12)0.0251 (11)0.0001 (9)0.0002 (8)0.0008 (8)
N40.0279 (11)0.0289 (11)0.0262 (11)0.0009 (9)0.0001 (9)0.0033 (8)
N50.0301 (12)0.0297 (12)0.0335 (12)0.0006 (10)0.0014 (10)0.0029 (9)
N60.0241 (10)0.0376 (13)0.0241 (11)0.0003 (9)0.0010 (8)0.0005 (9)
C10.0287 (12)0.0224 (11)0.0189 (11)0.0009 (9)0.0001 (9)0.0001 (8)
C20.0532 (17)0.0296 (13)0.0181 (12)0.0094 (12)0.0018 (11)0.0019 (10)
C30.0287 (12)0.0246 (12)0.0209 (11)0.0043 (9)0.0003 (9)0.0015 (9)
C40.0340 (14)0.0240 (12)0.0260 (12)0.0045 (10)0.0047 (10)0.0027 (9)
C50.0314 (13)0.0327 (14)0.0243 (12)0.0017 (11)0.0011 (10)0.0020 (10)
C60.0356 (16)0.0456 (19)0.056 (2)0.0089 (14)0.0027 (14)0.0125 (15)
C70.0290 (16)0.063 (2)0.067 (2)0.0072 (15)0.0011 (15)0.0106 (18)
C80.0284 (14)0.059 (2)0.0412 (17)0.0078 (14)0.0005 (12)0.0042 (14)
C90.0341 (14)0.0391 (16)0.0315 (14)0.0085 (12)0.0031 (11)0.0034 (11)
C100.0312 (13)0.0222 (11)0.0236 (12)0.0022 (10)0.0011 (9)0.0002 (9)
C110.0274 (12)0.0251 (12)0.0218 (11)0.0029 (9)0.0024 (9)0.0011 (9)
C120.0329 (14)0.0317 (14)0.0297 (13)0.0074 (11)0.0035 (11)0.0018 (10)
C130.0289 (14)0.0432 (17)0.0396 (16)0.0039 (12)0.0046 (11)0.0078 (13)
C140.0296 (14)0.0391 (16)0.0418 (16)0.0053 (12)0.0062 (12)0.0076 (12)
C150.0360 (14)0.0320 (14)0.0307 (14)0.0035 (11)0.0038 (11)0.0031 (11)
C160.0255 (12)0.0355 (14)0.0204 (11)0.0016 (10)0.0011 (9)0.0025 (10)
C170.0259 (12)0.0323 (13)0.0224 (12)0.0013 (10)0.0018 (9)0.0061 (10)
C180.0304 (14)0.0467 (17)0.0287 (14)0.0061 (12)0.0018 (11)0.0010 (12)
C190.0286 (15)0.062 (2)0.0427 (17)0.0100 (14)0.0026 (12)0.0078 (15)
C200.0267 (14)0.055 (2)0.061 (2)0.0028 (14)0.0026 (14)0.0151 (17)
C210.0357 (16)0.0374 (16)0.055 (2)0.0079 (13)0.0098 (14)0.0047 (14)
C220.0282 (12)0.0269 (12)0.0228 (11)0.0029 (10)0.0012 (9)0.0031 (9)
C230.0266 (12)0.0275 (12)0.0228 (12)0.0071 (10)0.0012 (9)0.0033 (9)
C240.0329 (14)0.0379 (15)0.0240 (12)0.0039 (11)0.0034 (10)0.0035 (10)
C250.0314 (14)0.0461 (17)0.0337 (15)0.0008 (12)0.0048 (11)0.0123 (12)
C260.0286 (14)0.0366 (15)0.0425 (16)0.0019 (11)0.0024 (11)0.0054 (12)
C270.0286 (13)0.0405 (16)0.0323 (14)0.0009 (11)0.0031 (11)0.0053 (11)
O10.0314 (11)0.0313 (11)0.0317 (10)0.0021 (9)0.0015 (8)0.0030 (8)
Cl10.0301 (3)0.0202 (3)0.0253 (3)0.0010 (2)0.0011 (2)0.0005 (2)
Cl20.0335 (3)0.0291 (3)0.0319 (3)0.0009 (3)0.0035 (2)0.0015 (2)
Cl30.0302 (3)0.0284 (3)0.0435 (4)0.0001 (3)0.0065 (3)0.0059 (3)
Cl40.0318 (4)0.0434 (4)0.0441 (4)0.0049 (3)0.0069 (3)0.0090 (3)
O110.0381 (11)0.0305 (10)0.0293 (10)0.0007 (8)0.0021 (8)0.0073 (8)
O130.0386 (12)0.0386 (12)0.0553 (14)0.0047 (9)0.0174 (10)0.0054 (10)
O120.0505 (13)0.0233 (10)0.0342 (10)0.0104 (9)0.0007 (9)0.0001 (8)
O140.0498 (13)0.0410 (12)0.0339 (11)0.0050 (10)0.0074 (9)0.0093 (9)
O210.0418 (12)0.0300 (11)0.0459 (12)0.0075 (9)0.0039 (9)0.0028 (9)
O220.110 (3)0.0619 (18)0.0301 (13)0.0273 (18)0.0094 (14)0.0031 (11)
O230.0500 (14)0.0407 (12)0.0445 (13)0.0157 (10)0.0098 (10)0.0026 (10)
O240.0445 (15)0.0543 (17)0.110 (3)0.0133 (13)0.0057 (16)0.0136 (17)
O310.0486 (17)0.0366 (15)0.185 (4)0.0123 (13)0.000 (2)0.002 (2)
O320.0435 (19)0.048 (2)0.357 (9)0.0187 (16)0.024 (3)0.020 (3)
O330.324 (8)0.056 (2)0.090 (3)0.067 (3)0.132 (4)0.031 (2)
O340.292 (8)0.054 (2)0.118 (4)0.023 (3)0.130 (5)0.004 (2)
O410.139 (4)0.287 (8)0.078 (3)0.164 (5)0.005 (3)0.011 (4)
O420.111 (4)0.115 (4)0.239 (7)0.062 (3)0.086 (4)0.075 (4)
O430.193 (6)0.235 (7)0.073 (3)0.150 (6)0.001 (3)0.018 (4)
O440.166 (6)0.212 (7)0.323 (10)0.084 (6)0.081 (6)0.224 (8)
Geometric parameters (Å, º) top
N1—C41.461 (3)C12—C131.382 (4)
N1—C101.463 (3)C12—H120.9500
N1—C11.480 (3)C16—H16A0.9900
N2—C161.459 (3)C16—H16B0.9900
N2—C221.469 (3)C27—C261.372 (4)
N2—C31.477 (3)C27—H270.9500
N4—C151.341 (4)C26—C251.386 (5)
N4—C111.341 (3)C26—H260.9500
N4—H4N0.87 (4)C9—C81.365 (5)
C1—C21.526 (3)C9—H90.9500
C1—H1A0.9900C14—C131.382 (5)
C1—H1B0.9900C14—H140.9500
C3—C21.522 (4)C18—C191.387 (4)
C3—H3A0.9900C18—H180.9500
C3—H3B0.9900C13—H130.9500
N6—C271.341 (4)C19—C201.389 (6)
N6—C231.354 (3)C19—H190.9500
N6—H6N0.90 (4)C8—C71.381 (5)
N5—C171.334 (4)C8—H80.9500
N5—C211.348 (4)C21—C201.365 (5)
N5—H5N0.78 (4)C21—H210.9500
N3—C51.336 (4)C6—C71.379 (5)
N3—C91.344 (4)C6—H60.9500
N3—H3N0.88 (4)C25—H250.9500
C4—C51.496 (4)C20—H200.9500
C4—H4A0.9900C7—H70.9500
C4—H4B0.9900Cl1—O121.429 (2)
C22—C231.510 (4)Cl1—O141.431 (2)
C22—H22A0.9900Cl1—O131.435 (2)
C22—H22B0.9900Cl1—O111.461 (2)
C10—C111.502 (4)Cl2—O221.426 (3)
C10—H10A0.9900Cl2—O241.433 (3)
C10—H10B0.9900Cl2—O231.444 (2)
C5—C61.381 (4)Cl2—O211.447 (2)
C17—C181.382 (4)Cl3—O331.349 (3)
C17—C161.507 (4)Cl3—O341.376 (4)
C24—C231.379 (4)Cl3—O321.398 (3)
C24—C251.389 (4)Cl3—O311.418 (3)
C24—H240.9500Cl4—O441.332 (5)
C11—C121.381 (4)Cl4—O411.369 (4)
C2—H2A0.9900Cl4—O421.379 (4)
C2—H2B0.9900Cl4—O431.381 (5)
C15—C141.377 (4)O1—H1020.76 (4)
C15—H150.9500O1—H1010.77 (5)
C4—N1—C10109.9 (2)C11—C12—H12120.2
C4—N1—C1112.7 (2)C13—C12—H12120.2
C10—N1—C1113.11 (19)N2—C16—C17110.9 (2)
C16—N2—C22114.3 (2)N2—C16—H16A109.5
C16—N2—C3111.0 (2)C17—C16—H16A109.5
C22—N2—C3115.6 (2)N2—C16—H16B109.5
C15—N4—C11123.3 (3)C17—C16—H16B109.5
C15—N4—H4N118 (3)H16A—C16—H16B108.0
C11—N4—H4N119 (3)N6—C27—C26120.1 (3)
N1—C1—C2115.6 (2)N6—C27—H27119.9
N1—C1—H1A108.4C26—C27—H27119.9
C2—C1—H1A108.4C27—C26—C25118.7 (3)
N1—C1—H1B108.4C27—C26—H26120.7
C2—C1—H1B108.4C25—C26—H26120.7
H1A—C1—H1B107.4N3—C9—C8119.4 (3)
N2—C3—C2111.8 (2)N3—C9—H9120.3
N2—C3—H3A109.3C8—C9—H9120.3
C2—C3—H3A109.3C15—C14—C13118.7 (3)
N2—C3—H3B109.3C15—C14—H14120.6
C2—C3—H3B109.3C13—C14—H14120.6
H3A—C3—H3B107.9C17—C18—C19118.9 (3)
C27—N6—C23123.5 (2)C17—C18—H18120.5
C27—N6—H6N122 (2)C19—C18—H18120.5
C23—N6—H6N114 (2)C12—C13—C14120.1 (3)
C17—N5—C21124.0 (3)C12—C13—H13119.9
C17—N5—H5N114 (3)C14—C13—H13119.9
C21—N5—H5N122 (3)C18—C19—C20120.3 (3)
C5—N3—C9123.7 (3)C18—C19—H19119.9
C5—N3—H3N120 (3)C20—C19—H19119.9
C9—N3—H3N116 (3)C9—C8—C7118.9 (3)
N1—C4—C5112.4 (2)C9—C8—H8120.6
N1—C4—H4A109.1C7—C8—H8120.6
C5—C4—H4A109.1N5—C21—C20119.0 (3)
N1—C4—H4B109.1N5—C21—H21120.5
C5—C4—H4B109.1C20—C21—H21120.5
H4A—C4—H4B107.9C7—C6—C5119.7 (3)
N2—C22—C23114.4 (2)C7—C6—H6120.1
N2—C22—H22A108.7C5—C6—H6120.1
C23—C22—H22A108.7C26—C25—C24119.6 (3)
N2—C22—H22B108.7C26—C25—H25120.2
C23—C22—H22B108.7C24—C25—H25120.2
H22A—C22—H22B107.6C21—C20—C19119.1 (3)
N1—C10—C11112.7 (2)C21—C20—H20120.4
N1—C10—H10A109.0C19—C20—H20120.4
C11—C10—H10A109.0C6—C7—C8120.2 (3)
N1—C10—H10B109.0C6—C7—H7119.9
C11—C10—H10B109.0C8—C7—H7119.9
H10A—C10—H10B107.8O12—Cl1—O14110.69 (14)
N3—C5—C6118.0 (3)O12—Cl1—O13109.99 (14)
N3—C5—C4118.7 (2)O14—Cl1—O13110.62 (15)
C6—C5—C4123.1 (3)O12—Cl1—O11108.75 (12)
N5—C17—C18118.7 (3)O14—Cl1—O11108.48 (14)
N5—C17—C16117.1 (2)O13—Cl1—O11108.25 (14)
C18—C17—C16124.1 (3)O22—Cl2—O24112.0 (2)
C23—C24—C25120.7 (3)O22—Cl2—O23108.57 (17)
C23—C24—H24119.6O24—Cl2—O23107.53 (18)
C25—C24—H24119.6O22—Cl2—O21109.80 (16)
N4—C11—C12118.5 (3)O24—Cl2—O21110.36 (17)
N4—C11—C10117.8 (2)O23—Cl2—O21108.43 (14)
C12—C11—C10123.6 (2)O33—Cl3—O34106.1 (5)
N6—C23—C24117.3 (3)O33—Cl3—O32108.8 (4)
N6—C23—C22119.1 (2)O34—Cl3—O32108.9 (4)
C24—C23—C22123.5 (2)O33—Cl3—O31108.5 (3)
C3—C2—C1110.8 (2)O34—Cl3—O31109.9 (3)
C3—C2—H2A109.5O32—Cl3—O31114.3 (2)
C1—C2—H2A109.5O44—Cl4—O41114.0 (5)
C3—C2—H2B109.5O44—Cl4—O42107.1 (4)
C1—C2—H2B109.5O41—Cl4—O42117.2 (5)
H2A—C2—H2B108.1O44—Cl4—O43113.3 (6)
N4—C15—C14119.7 (3)O41—Cl4—O43102.4 (3)
N4—C15—H15120.2O42—Cl4—O43102.3 (5)
C14—C15—H15120.2H102—O1—H101111 (5)
C11—C12—C13119.7 (3)
C4—N1—C1—C268.0 (3)N1—C1—C2—C3178.8 (2)
C10—N1—C1—C257.5 (3)C11—N4—C15—C140.1 (4)
C16—N2—C3—C2161.5 (2)N4—C11—C12—C130.0 (4)
C22—N2—C3—C266.1 (3)C10—C11—C12—C13177.1 (3)
C10—N1—C4—C5157.3 (2)C22—N2—C16—C17138.2 (2)
C1—N1—C4—C575.5 (3)C3—N2—C16—C1788.8 (3)
C16—N2—C22—C2372.1 (3)N5—C17—C16—N213.3 (3)
C3—N2—C22—C2358.7 (3)C18—C17—C16—N2170.2 (3)
C4—N1—C10—C11166.5 (2)C23—N6—C27—C261.0 (4)
C1—N1—C10—C1166.5 (3)N6—C27—C26—C251.3 (5)
C9—N3—C5—C60.8 (4)C5—N3—C9—C81.1 (4)
C9—N3—C5—C4174.4 (3)N4—C15—C14—C130.8 (4)
N1—C4—C5—N320.6 (3)N5—C17—C18—C191.0 (4)
N1—C4—C5—C6164.4 (3)C16—C17—C18—C19175.4 (3)
C21—N5—C17—C180.9 (4)C11—C12—C13—C140.7 (4)
C21—N5—C17—C16177.5 (3)C15—C14—C13—C121.1 (5)
C15—N4—C11—C120.3 (4)C17—C18—C19—C201.6 (5)
C15—N4—C11—C10177.0 (2)N3—C9—C8—C71.8 (5)
N1—C10—C11—N442.1 (3)C17—N5—C21—C202.1 (5)
N1—C10—C11—C12140.8 (2)N3—C5—C6—C71.9 (5)
C27—N6—C23—C240.5 (4)C4—C5—C6—C7173.1 (3)
C27—N6—C23—C22177.9 (3)C27—C26—C25—C240.1 (5)
C25—C24—C23—N61.6 (4)C23—C24—C25—C261.3 (4)
C25—C24—C23—C22176.7 (3)N5—C21—C20—C191.4 (5)
N2—C22—C23—N685.1 (3)C18—C19—C20—C210.4 (5)
N2—C22—C23—C2493.2 (3)C5—C6—C7—C81.2 (6)
N2—C3—C2—C1175.3 (2)C9—C8—C7—C60.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O11i0.88 (4)2.00 (4)2.845 (3)160 (4)
N3—H3N···N10.88 (4)2.38 (4)2.737 (3)105 (3)
N4—H4N···O1i0.87 (4)2.57 (4)3.137 (3)124 (3)
N5—H5N···N20.78 (4)2.23 (4)2.659 (3)115 (4)
N6—H6N···O10.90 (4)1.93 (4)2.810 (3)165 (3)
O1—H102···O210.76 (4)2.14 (4)2.876 (3)163 (4)
O1—H101···O33ii0.77 (5)2.41 (5)3.088 (7)147 (5)
Symmetry codes: (i) x, y, z1; (ii) x+1, y+1, z+1.
 

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