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The inclusion complex, C6H10N22+·2I-·C36H36N24O12.10H2O, displays a large ellipsoidal deformation of the cucurbit[6]uril skeleton upon complex formation. The cucurbit[6]uril mol­ecule and the phenyl­enediammonium dication are each disposed about a center of inversion.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680700387X/tk2125sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680700387X/tk2125Isup2.hkl
Contains datablock I

CCDC reference: 636820

Key indicators

  • Single-crystal X-ray study
  • T = 223 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.035
  • wR factor = 0.085
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.841(10) ...... 4.00 su-Ra O1W -H11W 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.83(3), Rep 0.829(10) ...... 3.00 su-Ra O1W -H12W 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(4), Rep 0.844(10) ...... 4.00 su-Ra O2W -H21W 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.844(10) ...... 4.00 su-Ra O2W -H22W 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.83(3), Rep 0.826(10) ...... 3.00 su-Ra O3W -H32W 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.85(3), Rep 0.849(10) ...... 3.00 su-Ra O4W -H41W 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.842(10) ...... 3.00 su-Ra O4W -H42W 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.83(4), Rep 0.832(10) ...... 4.00 su-Ra O5W -H51W 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(4), Rep 0.834(10) ...... 4.00 su-Ra O5W -H52W 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 102(5), Rep 102(2) ...... 2.50 su-Ra H21W -O2W -H22W 1.555 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.841(10) ...... 4.00 su-Ra O1W -H11W 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.83(3), Rep 0.829(10) ...... 3.00 su-Ra O1W -H12W 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.83(3), Rep 0.829(10) ...... 3.00 su-Ra O1W -H12W 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(4), Rep 0.844(10) ...... 4.00 su-Ra O2W -H21W 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.844(10) ...... 4.00 su-Ra O2W -H22W 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.83(3), Rep 0.826(10) ...... 3.00 su-Ra O3W -H32W 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.85(3), Rep 0.849(10) ...... 3.00 su-Ra O4W -H41W 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.842(10) ...... 3.00 su-Ra O4W -H42W 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.83(4), Rep 0.832(10) ...... 4.00 su-Ra O5W -H51W 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(4), Rep 0.834(10) ...... 4.00 su-Ra O5W -H52W 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.93(4), Rep 1.923(19) ...... 2.11 su-Ra H22W -O33 1.555 1.655 PLAT736_ALERT_1_C H...A Calc 2.77(4), Rep 2.769(15) ...... 2.67 su-Ra H51W -I1 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 25 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 25 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XSHELL (Bruker, 1999); software used to prepare material for publication: SHELXL97.

Cucurbit[6]uril p-phenylenediammonium diiodide decahydrate top
Crystal data top
C6H10N22+·2I·C36H36N24O12·10H2OF(000) = 1564
Mr = 1541.01Dx = 1.828 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6948 reflections
a = 11.854 (3) Åθ = 2.1–28.3°
b = 15.460 (4) ŵ = 1.23 mm1
c = 15.279 (4) ÅT = 223 K
β = 90.447 (4)°Prism, yellow
V = 2800.1 (11) Å30.32 × 0.23 × 0.21 mm
Z = 2
Data collection top
Three-circle
diffractometer
6417 independent reflections
Radiation source: fine-focus sealed tube5677 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 8.33 pixels mm-1θmax = 27.5°, θmin = 2.5°
ω and φ scansh = 1515
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2019
Tmin = 0.720, Tmax = 0.773l = 1919
31829 measured 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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.02P)2 + 9.444P], P = (max(Fo2,0) + 2Fc2)/3
6417 reflections(Δ/σ)max < 0.001
446 parametersΔρmax = 0.83 e Å3
18 restraintsΔρmin = 0.94 e Å3
Special details top

Experimental. 3 omega runs of 606 frames at phi=60,180,300 and 1 phi run of 847 frames. Step size =-0.3 deg; exposure 23 sec.

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
I10.228768 (18)0.501545 (13)0.000747 (13)0.03403 (7)
N10.7229 (2)0.54985 (17)0.45318 (17)0.0317 (5)
H1A0.75850.57230.50020.048*
H1B0.71930.58990.41050.048*
H1C0.76110.50340.43400.048*
C10.6081 (2)0.52380 (18)0.47751 (19)0.0260 (5)
C20.5707 (3)0.5390 (2)0.5604 (2)0.0385 (7)
H20.61860.56520.60200.046*
C30.4618 (3)0.5155 (3)0.5830 (2)0.0436 (8)
H30.43560.52650.63980.052*
N100.43844 (19)0.38962 (15)0.18776 (16)0.0269 (5)
C110.5250 (2)0.44380 (17)0.15035 (18)0.0240 (5)
H110.54080.42780.08890.029*
N120.62852 (18)0.45090 (14)0.20237 (15)0.0227 (4)
C130.3508 (2)0.43690 (18)0.22087 (17)0.0248 (5)
O130.26468 (16)0.40702 (13)0.25198 (14)0.0312 (4)
C140.6547 (2)0.53503 (18)0.22118 (17)0.0243 (5)
O140.74200 (16)0.56062 (14)0.25574 (14)0.0313 (4)
N150.37653 (18)0.52329 (15)0.21319 (15)0.0236 (4)
C160.4742 (2)0.53624 (17)0.15719 (18)0.0236 (5)
H160.45220.55940.09910.028*
N170.56535 (18)0.58571 (15)0.19654 (16)0.0257 (5)
C180.2893 (2)0.58831 (18)0.22567 (19)0.0266 (5)
H18A0.28290.62330.17240.032*
H18B0.21690.55910.23440.032*
C190.5619 (2)0.67727 (18)0.21462 (19)0.0273 (6)
H19A0.52610.70660.16480.033*
H19B0.63950.69870.21950.033*
N200.31094 (19)0.64486 (15)0.29920 (15)0.0254 (5)
C210.3830 (2)0.72033 (17)0.29345 (17)0.0232 (5)
H210.36130.75800.24370.028*
N220.50201 (18)0.70065 (15)0.29340 (16)0.0259 (5)
C230.2517 (2)0.64159 (18)0.37562 (18)0.0251 (5)
O230.18261 (17)0.58696 (14)0.39595 (14)0.0338 (5)
C240.5557 (2)0.72665 (16)0.36901 (19)0.0251 (5)
O240.65678 (16)0.72046 (13)0.38415 (14)0.0313 (4)
N250.28132 (19)0.71299 (15)0.42437 (15)0.0253 (5)
C260.3654 (2)0.76587 (17)0.38254 (17)0.0231 (5)
H260.34000.82590.37380.028*
N270.47668 (19)0.76124 (15)0.42382 (15)0.0257 (5)
C280.2190 (2)0.7404 (2)0.50036 (17)0.0270 (6)
H28A0.14710.70910.50150.032*
H28B0.20200.80210.49470.032*
C290.5059 (2)0.81238 (18)0.50042 (18)0.0267 (5)
H29A0.58770.82160.50120.032*
H29B0.46980.86920.49500.032*
N300.27749 (19)0.72627 (16)0.58276 (15)0.0266 (5)
C310.3614 (2)0.78389 (17)0.62051 (18)0.0250 (5)
H310.33600.84490.62000.030*
N320.47334 (19)0.77415 (16)0.58318 (16)0.0273 (5)
C330.2493 (2)0.66074 (18)0.63801 (17)0.0246 (5)
O330.18299 (16)0.60210 (14)0.62093 (13)0.0305 (4)
C340.5516 (2)0.75020 (17)0.64527 (19)0.0264 (5)
O340.65351 (16)0.74796 (14)0.63445 (15)0.0336 (5)
N350.30454 (19)0.67265 (15)0.71586 (15)0.0253 (5)
C360.3766 (2)0.74857 (17)0.71570 (18)0.0252 (5)
H360.35340.79150.76020.030*
N370.49631 (19)0.72989 (16)0.72072 (16)0.0270 (5)
C380.2883 (2)0.61760 (18)0.79139 (17)0.0251 (5)
H38A0.21280.59180.78820.030*
H38B0.29210.65300.84450.030*
C390.5539 (2)0.70307 (18)0.80061 (19)0.0284 (6)
H39A0.63030.72720.80060.034*
H39B0.51410.72770.85080.034*
O1W0.1706 (2)0.3561 (2)0.41969 (18)0.0523 (7)
H11W0.117 (3)0.387 (3)0.401 (3)0.078*
H12W0.215 (3)0.350 (3)0.3784 (19)0.078*
O2W0.9822 (3)0.6077 (2)0.7085 (3)0.0659 (8)
H21W0.974 (5)0.563 (2)0.740 (3)0.099*
H22W1.040 (3)0.595 (3)0.680 (3)0.099*
O3W0.9051 (3)0.7979 (2)0.5053 (2)0.0649 (8)
H31W0.889 (4)0.7463 (11)0.513 (4)0.097*
H32W0.845 (2)0.825 (3)0.510 (4)0.097*
O4W0.9412 (3)0.5969 (2)0.3665 (3)0.0714 (9)
H41W0.938 (3)0.577 (4)0.3149 (17)0.107*
H42W1.004 (2)0.578 (3)0.383 (3)0.107*
O5W0.0048 (3)0.5178 (3)0.1569 (2)0.0763 (10)
H51W0.062 (3)0.513 (4)0.126 (3)0.114*
H52W0.047 (3)0.501 (4)0.123 (3)0.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.03898 (12)0.03138 (11)0.03170 (11)0.00423 (8)0.00214 (8)0.00152 (8)
N10.0281 (12)0.0362 (14)0.0310 (13)0.0045 (10)0.0022 (10)0.0022 (11)
C10.0228 (12)0.0241 (13)0.0313 (14)0.0007 (10)0.0009 (10)0.0026 (11)
C20.0353 (16)0.052 (2)0.0285 (15)0.0137 (14)0.0035 (12)0.0086 (14)
C30.0395 (18)0.067 (2)0.0244 (14)0.0121 (16)0.0057 (13)0.0117 (15)
N100.0233 (11)0.0217 (11)0.0357 (13)0.0000 (9)0.0039 (9)0.0018 (9)
C110.0236 (12)0.0247 (13)0.0237 (12)0.0018 (10)0.0041 (10)0.0011 (10)
N120.0203 (10)0.0227 (11)0.0252 (11)0.0028 (8)0.0018 (8)0.0009 (9)
C130.0238 (12)0.0255 (13)0.0250 (13)0.0010 (10)0.0070 (10)0.0013 (10)
O130.0242 (10)0.0303 (11)0.0391 (11)0.0048 (8)0.0024 (8)0.0043 (9)
C140.0221 (12)0.0264 (13)0.0246 (13)0.0006 (10)0.0038 (10)0.0006 (10)
O140.0223 (9)0.0318 (11)0.0398 (11)0.0024 (8)0.0034 (8)0.0033 (9)
N150.0198 (10)0.0236 (11)0.0276 (11)0.0008 (8)0.0002 (8)0.0005 (9)
C160.0221 (12)0.0236 (13)0.0250 (13)0.0011 (10)0.0013 (10)0.0021 (10)
N170.0204 (10)0.0222 (11)0.0345 (12)0.0000 (8)0.0001 (9)0.0020 (9)
C180.0214 (12)0.0270 (13)0.0314 (14)0.0017 (10)0.0045 (10)0.0037 (11)
C190.0265 (13)0.0225 (13)0.0331 (14)0.0030 (10)0.0066 (11)0.0020 (11)
N200.0252 (11)0.0240 (11)0.0268 (11)0.0034 (9)0.0016 (9)0.0029 (9)
C210.0231 (12)0.0215 (12)0.0251 (13)0.0016 (10)0.0002 (10)0.0022 (10)
N220.0203 (10)0.0264 (11)0.0309 (12)0.0009 (9)0.0020 (9)0.0016 (9)
C230.0209 (12)0.0266 (13)0.0278 (13)0.0034 (10)0.0025 (10)0.0022 (11)
O230.0280 (10)0.0343 (11)0.0390 (12)0.0075 (9)0.0048 (9)0.0006 (9)
C240.0246 (13)0.0164 (11)0.0345 (14)0.0020 (9)0.0010 (10)0.0034 (10)
O240.0206 (9)0.0299 (10)0.0435 (12)0.0017 (8)0.0013 (8)0.0002 (9)
N250.0227 (11)0.0295 (12)0.0236 (11)0.0022 (9)0.0023 (8)0.0014 (9)
C260.0225 (12)0.0203 (12)0.0264 (13)0.0024 (9)0.0016 (10)0.0017 (10)
N270.0208 (10)0.0267 (12)0.0296 (12)0.0011 (9)0.0035 (9)0.0019 (9)
C280.0221 (12)0.0354 (15)0.0234 (13)0.0043 (11)0.0019 (10)0.0007 (11)
C290.0259 (13)0.0228 (13)0.0314 (14)0.0037 (10)0.0018 (11)0.0006 (11)
N300.0241 (11)0.0321 (12)0.0235 (11)0.0016 (9)0.0036 (9)0.0031 (9)
C310.0235 (12)0.0221 (12)0.0294 (13)0.0025 (10)0.0030 (10)0.0010 (10)
N320.0208 (11)0.0311 (12)0.0298 (12)0.0006 (9)0.0028 (9)0.0047 (10)
C330.0216 (12)0.0279 (13)0.0242 (13)0.0043 (10)0.0008 (10)0.0005 (10)
O330.0256 (10)0.0347 (11)0.0312 (10)0.0058 (8)0.0014 (8)0.0009 (9)
C340.0258 (13)0.0183 (12)0.0351 (15)0.0009 (10)0.0065 (11)0.0001 (11)
O340.0214 (9)0.0331 (11)0.0463 (12)0.0022 (8)0.0050 (8)0.0062 (9)
N350.0271 (11)0.0256 (11)0.0231 (11)0.0011 (9)0.0032 (9)0.0021 (9)
C360.0256 (13)0.0216 (12)0.0283 (13)0.0040 (10)0.0033 (10)0.0011 (10)
N370.0233 (11)0.0292 (12)0.0285 (12)0.0021 (9)0.0062 (9)0.0029 (10)
C380.0236 (12)0.0273 (13)0.0245 (13)0.0058 (10)0.0021 (10)0.0022 (10)
C390.0318 (14)0.0215 (13)0.0318 (14)0.0015 (11)0.0114 (11)0.0027 (11)
O1W0.0501 (15)0.0591 (17)0.0479 (15)0.0156 (13)0.0070 (12)0.0083 (13)
O2W0.0457 (16)0.063 (2)0.089 (2)0.0026 (14)0.0166 (15)0.0045 (17)
O3W0.069 (2)0.0525 (17)0.074 (2)0.0078 (15)0.0012 (17)0.0040 (16)
O4W0.0493 (17)0.074 (2)0.091 (2)0.0027 (16)0.0110 (16)0.0022 (19)
O5W0.0505 (18)0.114 (3)0.064 (2)0.001 (2)0.0051 (15)0.018 (2)
Geometric parameters (Å, º) top
N1—C11.470 (3)N25—C261.442 (3)
N1—H1A0.9000N25—C281.444 (3)
N1—H1B0.9000C26—N271.460 (3)
N1—H1C0.9000C26—H260.9848
C1—C21.365 (4)N27—C291.452 (4)
C1—C3i1.378 (4)C28—N301.449 (3)
C2—C31.387 (5)C28—H28A0.9800
C2—H20.9400C28—H28B0.9800
C3—C1i1.378 (4)C29—N321.451 (4)
C3—H30.9400C29—H29A0.9800
N10—C131.370 (4)C29—H29B0.9800
N10—C111.446 (3)N30—C331.362 (4)
N10—C39i1.447 (3)N30—C311.451 (3)
C11—N121.461 (3)C31—N321.456 (3)
C11—C161.555 (4)C31—C361.563 (4)
C11—H110.9900C31—H310.9900
N12—C141.367 (4)N32—C341.372 (3)
N12—C38i1.450 (3)C33—O331.227 (3)
C13—O131.220 (3)C33—N351.366 (3)
C13—N151.375 (3)C34—O341.221 (3)
C14—O141.224 (3)C34—N371.367 (4)
C14—N171.368 (3)N35—C381.448 (3)
N15—C181.455 (3)N35—C361.452 (3)
N15—C161.459 (3)C36—N371.450 (3)
C16—N171.451 (3)C36—H360.9900
C16—H160.9900N37—C391.454 (3)
N17—C191.443 (3)C38—N12i1.450 (3)
C18—N201.445 (3)C38—H38A0.9800
C18—H18A0.9800C38—H38B0.9800
C18—H18B0.9800C39—N10i1.447 (3)
C19—N221.448 (4)C39—H39A0.9800
C19—H19A0.9800C39—H39B0.9800
C19—H19B0.9800O1W—H11W0.841 (10)
N20—C231.368 (4)O1W—H12W0.829 (10)
N20—C211.449 (3)O2W—H21W0.844 (10)
C21—N221.444 (3)O2W—H22W0.844 (10)
C21—C261.548 (4)O3W—H31W0.830 (10)
C21—H210.9900O3W—H32W0.826 (10)
N22—C241.375 (4)O4W—H41W0.849 (10)
C23—O231.218 (3)O4W—H42W0.842 (10)
C23—N251.376 (4)O5W—H51W0.832 (10)
C24—O241.223 (3)O5W—H52W0.834 (10)
C24—N271.370 (4)
C1—N1—H1A109.5O24—C24—N22125.6 (3)
C1—N1—H1B109.5N27—C24—N22108.3 (2)
H1A—N1—H1B109.5C23—N25—C26112.9 (2)
C1—N1—H1C109.5C23—N25—C28122.7 (2)
H1A—N1—H1C109.5C26—N25—C28123.3 (2)
H1B—N1—H1C109.5N25—C26—N27114.0 (2)
C2—C1—C3i120.0 (3)N25—C26—C21103.3 (2)
C2—C1—N1119.7 (3)N27—C26—C21103.3 (2)
C3i—C1—N1120.3 (3)N25—C26—H26112.5
C1—C2—C3119.7 (3)N27—C26—H26112.3
C1—C2—H2120.2C21—C26—H26110.6
C3—C2—H2120.2C24—N27—C29123.0 (2)
C1i—C3—C2120.3 (3)C24—N27—C26112.0 (2)
C1i—C3—H3119.8C29—N27—C26122.1 (2)
C2—C3—H3119.8N25—C28—N30114.2 (2)
C13—N10—C11112.3 (2)N25—C28—H28A108.7
C13—N10—C39i122.0 (2)N30—C28—H28A108.7
C11—N10—C39i125.3 (2)N25—C28—H28B108.7
N10—C11—N12115.1 (2)N30—C28—H28B108.7
N10—C11—C16103.3 (2)H28A—C28—H28B107.6
N12—C11—C16102.6 (2)N32—C29—N27114.6 (2)
N10—C11—H11111.7N32—C29—H29A108.6
N12—C11—H11111.7N27—C29—H29A108.6
C16—C11—H11111.7N32—C29—H29B108.6
C14—N12—C38i121.9 (2)N27—C29—H29B108.6
C14—N12—C11112.0 (2)H29A—C29—H29B107.6
C38i—N12—C11123.3 (2)C33—N30—C28122.2 (2)
O13—C13—N10125.5 (3)C33—N30—C31112.4 (2)
O13—C13—N15126.0 (3)C28—N30—C31125.1 (2)
N10—C13—N15108.5 (2)N30—C31—N32113.9 (2)
O14—C14—N12126.0 (3)N30—C31—C36103.2 (2)
O14—C14—N17125.7 (3)N32—C31—C36103.3 (2)
N12—C14—N17108.2 (2)N30—C31—H31111.9
C13—N15—C18120.1 (2)N32—C31—H31111.9
C13—N15—C16111.2 (2)C36—C31—H31111.9
C18—N15—C16123.3 (2)C34—N32—C29121.9 (2)
N17—C16—N15114.9 (2)C34—N32—C31111.7 (2)
N17—C16—C11103.0 (2)C29—N32—C31123.3 (2)
N15—C16—C11102.9 (2)O33—C33—N30125.3 (3)
N17—C16—H16111.8O33—C33—N35125.9 (3)
N15—C16—H16111.8N30—C33—N35108.8 (2)
C11—C16—H16111.8O34—C34—N37126.1 (3)
C14—N17—C19122.2 (2)O34—C34—N32125.3 (3)
C14—N17—C16112.6 (2)N37—C34—N32108.6 (2)
C19—N17—C16125.1 (2)C33—N35—C38123.3 (2)
N20—C18—N15113.5 (2)C33—N35—C36112.7 (2)
N20—C18—H18A108.9C38—N35—C36124.0 (2)
N15—C18—H18A108.9N37—C36—N35114.5 (2)
N20—C18—H18B108.9N37—C36—C31103.0 (2)
N15—C18—H18B108.9N35—C36—C31102.7 (2)
H18A—C18—H18B107.7N37—C36—H36112.0
N17—C19—N22114.8 (2)N35—C36—H36112.0
N17—C19—H19A108.6C31—C36—H36112.0
N22—C19—H19A108.6C34—N37—C36112.7 (2)
N17—C19—H19B108.6C34—N37—C39123.3 (2)
N22—C19—H19B108.6C36—N37—C39123.6 (2)
H19A—C19—H19B107.6N35—C38—N12i112.8 (2)
C23—N20—C18123.5 (2)N35—C38—H38A109.0
C23—N20—C21112.8 (2)N12i—C38—H38A109.0
C18—N20—C21122.8 (2)N35—C38—H38B109.0
N22—C21—N20114.0 (2)N12i—C38—H38B109.0
N22—C21—C26103.6 (2)H38A—C38—H38B107.8
N20—C21—C26103.3 (2)N10i—C39—N37114.5 (2)
N22—C21—H21111.8N10i—C39—H39A108.6
N20—C21—H21111.8N37—C39—H39A108.6
C26—C21—H21111.8N10i—C39—H39B108.6
C24—N22—C21112.6 (2)N37—C39—H39B108.6
C24—N22—C19123.0 (2)H39A—C39—H39B107.6
C21—N22—C19122.6 (2)H11W—O1W—H12W106 (2)
O23—C23—N20126.4 (3)H21W—O2W—H22W102 (2)
O23—C23—N25126.0 (3)H31W—O3W—H32W105 (2)
N20—C23—N25107.6 (2)H41W—O4W—H42W101 (2)
O24—C24—N27126.1 (3)H51W—O5W—H52W103 (2)
C3i—C1—C2—C30.7 (6)N20—C23—N25—C28166.9 (2)
N1—C1—C2—C3179.1 (3)C23—N25—C26—N27108.2 (3)
C1—C2—C3—C1i0.7 (6)C28—N25—C26—N2783.2 (3)
C13—N10—C11—N12106.3 (3)C23—N25—C26—C213.2 (3)
C39i—N10—C11—N1266.9 (3)C28—N25—C26—C21165.4 (2)
C13—N10—C11—C164.8 (3)N22—C21—C26—N25122.3 (2)
C39i—N10—C11—C16177.9 (2)N20—C21—C26—N253.2 (3)
N10—C11—N12—C14124.0 (2)N22—C21—C26—N273.3 (3)
C16—C11—N12—C1412.6 (3)N20—C21—C26—N27115.8 (2)
N10—C11—N12—C38i74.9 (3)O24—C24—N27—C2913.7 (4)
C16—C11—N12—C38i173.7 (2)N22—C24—N27—C29165.8 (2)
C11—N10—C13—O13176.1 (3)O24—C24—N27—C26174.8 (3)
C39i—N10—C13—O1310.4 (4)N22—C24—N27—C264.7 (3)
C11—N10—C13—N154.0 (3)N25—C26—N27—C24116.3 (3)
C39i—N10—C13—N15169.4 (2)C21—C26—N27—C245.0 (3)
C38i—N12—C14—O1410.6 (4)N25—C26—N27—C2982.4 (3)
C11—N12—C14—O14172.0 (3)C21—C26—N27—C29166.3 (2)
C38i—N12—C14—N17170.7 (2)C23—N25—C28—N30108.7 (3)
C11—N12—C14—N179.3 (3)C26—N25—C28—N3083.8 (3)
O13—C13—N15—C1813.3 (4)C24—N27—C29—N32116.0 (3)
N10—C13—N15—C18166.8 (2)C26—N27—C29—N3284.7 (3)
O13—C13—N15—C16168.2 (3)N25—C28—N30—C33104.3 (3)
N10—C13—N15—C1612.0 (3)N25—C28—N30—C3183.1 (3)
C13—N15—C16—N17125.4 (2)C33—N30—C31—N32106.5 (3)
C18—N15—C16—N1780.7 (3)C28—N30—C31—N3280.3 (3)
C13—N15—C16—C1114.3 (3)C33—N30—C31—C364.7 (3)
C18—N15—C16—C11168.2 (2)C28—N30—C31—C36168.5 (2)
N10—C11—C16—N17130.7 (2)N27—C29—N32—C34116.6 (3)
N12—C11—C16—N1710.8 (3)N27—C29—N32—C3184.8 (3)
N10—C11—C16—N1511.0 (2)N30—C31—N32—C34119.4 (3)
N12—C11—C16—N15109.0 (2)C36—C31—N32—C348.2 (3)
O14—C14—N17—C194.2 (4)N30—C31—N32—C2980.1 (3)
N12—C14—N17—C19174.4 (2)C36—C31—N32—C29168.7 (2)
O14—C14—N17—C16180.0 (3)C28—N30—C33—O338.7 (4)
N12—C14—N17—C161.4 (3)C31—N30—C33—O33177.8 (3)
N15—C16—N17—C14104.8 (3)C28—N30—C33—N35169.5 (2)
C11—C16—N17—C146.2 (3)C31—N30—C33—N353.9 (3)
N15—C16—N17—C1970.8 (3)C29—N32—C34—O349.6 (4)
C11—C16—N17—C19178.1 (2)C31—N32—C34—O34170.4 (3)
C13—N15—C18—N20117.0 (3)C29—N32—C34—N37170.2 (2)
C16—N15—C18—N2091.3 (3)C31—N32—C34—N379.3 (3)
C14—N17—C19—N2295.6 (3)O33—C33—N35—C382.3 (4)
C16—N17—C19—N2279.7 (3)N30—C33—N35—C38176.0 (2)
N15—C18—N20—C23108.0 (3)O33—C33—N35—C36179.5 (3)
N15—C18—N20—C2183.6 (3)N30—C33—N35—C361.2 (3)
C23—N20—C21—N22114.0 (3)C33—N35—C36—N37112.5 (3)
C18—N20—C21—N2276.4 (3)C38—N35—C36—N3770.3 (3)
C23—N20—C21—C262.4 (3)C33—N35—C36—C311.7 (3)
C18—N20—C21—C26172.0 (2)C38—N35—C36—C31178.9 (2)
N20—C21—N22—C24110.6 (3)N30—C31—C36—N37122.9 (2)
C26—C21—N22—C240.8 (3)N32—C31—C36—N374.0 (3)
N20—C21—N22—C1984.3 (3)N30—C31—C36—N353.6 (3)
C26—C21—N22—C19164.3 (2)N32—C31—C36—N35115.2 (2)
N17—C19—N22—C24105.7 (3)O34—C34—N37—C36173.3 (3)
N17—C19—N22—C2190.8 (3)N32—C34—N37—C366.4 (3)
C18—N20—C23—O237.9 (4)O34—C34—N37—C390.7 (4)
C21—N20—C23—O23177.4 (3)N32—C34—N37—C39179.0 (2)
C18—N20—C23—N25170.0 (2)N35—C36—N37—C34111.9 (3)
C21—N20—C23—N250.5 (3)C31—C36—N37—C341.2 (3)
C21—N22—C24—O24177.2 (3)N35—C36—N37—C3975.5 (3)
C19—N22—C24—O2412.2 (4)C31—C36—N37—C39173.8 (2)
C21—N22—C24—N272.3 (3)C33—N35—C38—N12i95.0 (3)
C19—N22—C24—N27167.3 (2)C36—N35—C38—N12i88.1 (3)
O23—C23—N25—C26179.8 (3)C34—N37—C39—N10i95.6 (3)
N20—C23—N25—C261.8 (3)C36—N37—C39—N10i92.6 (3)
O23—C23—N25—C2811.1 (4)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1Wi0.901.852.728 (4)165
N1—H1B···O240.902.192.945 (3)141
N1—H1C···O33i0.901.952.840 (3)169
O1W—H11W···O2Wi0.84 (1)2.04 (3)2.716 (5)137 (4)
O1W—H12W···O34i0.83 (1)2.19 (3)2.765 (4)127 (3)
O1W—H12W···O130.83 (1)2.21 (3)2.911 (3)143 (4)
O2W—H21W···O5Wi0.84 (1)2.03 (3)2.831 (5)158 (6)
O2W—H22W···O33ii0.84 (1)1.92 (2)2.741 (4)163 (5)
O3W—H31W···O1Wi0.83 (1)2.02 (3)2.793 (4)156 (6)
O3W—H32W···I1iii0.83 (1)3.03 (3)3.740 (4)146 (4)
O4W—H41W···O140.85 (1)2.49 (4)2.948 (4)114 (3)
O4W—H42W···O23ii0.84 (1)2.13 (3)2.898 (4)152 (5)
O5W—H51W···I10.83 (1)2.77 (2)3.592 (4)171 (5)
O5W—H52W···I1iv0.83 (1)2.86 (2)3.668 (3)163 (6)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z; (iii) x+1/2, y+3/2, z+1/2; (iv) x, y+1, z.
 

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