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Acta Crystallogr Sect E Struct Rep Online. 2009 September 1; 65(Pt 9): o2129.
Published online 2009 August 12. doi:  10.1107/S1600536809030852
PMCID: PMC2969953

(E)-2,4-Dihydroxy­benzaldehyde 4-ethyl­thio­semicarbazone–4,4′-bipyridine–water (4/7/2)

Abstract

The asymmetric unit of the title compound, 7C10H8N2·4C10H13N3O2S·2H2O, contains two independent 2,4-hydroxy­benzaldehyde 4-ethyl­thio­semicarbazone mol­ecules, three and a half 4,4′-bipyridine mol­ecules and one water mol­ecule. Two of the 4,4′-bipyridine mol­ecules lie on general positions and the other three on centers of inversion. The two 4,4′-bipyridine mol­ecules on general positions and one of the three on special positions are disordered over two positions each with an occupancy of 0.50. The –NH—C(=S)—NH—NC fragment is close to planar in the two 2,4-hydroxy­benzaldehyde 4-ethyl­thio­semicarbazone mol­ecules (r.m.s. deviations = 0.04 and 0.05 Å). In the crystal, the Schiff base, N-heterocycle and water mol­ecules engage in O—H(...)O, O—H(...)N and N—H(...)O hydrogen-bonding inter­actions, generating a layer structure.

Related literature

4,4′-Bipyridine forms a number of clathrates with diphenols; for the quinol clathrate, see: Oswald et al. (2005 [triangle]) and for the 2,2′-biphenol clathrate, see: Lavender et al. (1999 [triangle]). For the crystal structure of 2,4-dihydroxy­benzaldehyde 4-ethyl­thio­semicarbazone, see: Tan et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2129-scheme1.jpg

Experimental

Crystal data

  • 7C10H8N2·4C10H13N3O2S·2H2O
  • M r = 2086.50
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2129-efi1.jpg
  • a = 11.7683 (3) Å
  • b = 15.2531 (4) Å
  • c = 16.0612 (4) Å
  • α = 74.639 (2)°
  • β = 86.561 (2)°
  • γ = 70.252 (1)°
  • V = 2615.2 (1) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.16 mm−1
  • T = 153 K
  • 0.20 × 0.20 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.968, T max = 0.992
  • 18419 measured reflections
  • 10042 independent reflections
  • 6419 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.179
  • S = 1.02
  • 10042 reflections
  • 686 parameters
  • 170 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.66 e Å−3
  • Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030852/ci2864sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030852/ci2864Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The author thanks the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

2,4-Dihydroxybenzaldehyde ethylthiosemicarbazone (0.48 g, 2 mmol) and 4,4'-bipyridine (0.15 g, 1 mmol) were dissolved in ethanol (20 ml) and the solution was set aside for a week. The solid material that separated from the solution consisted of small, transparent crystals embedded in some yellow, opaque clumps.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H = 0.95–0.98 Å) and were included in the refinement in the riding-model approximation, with U(H) set to 1.2 to 1.5Ueq(C). The amino and water H-atoms were located in a difference Fourier map, and were refined with distance restraints (O—H = 0.84 (1) and N—H = 0.88 (1) Å); their Uiso parameters were freely refined.

The two 4,4'-bipyridine molecules on general positions and one of the three on special positions are disordered over two positions. A consideration of the short C···C contacts necessitated a 1:1 type of disorder. For these, the pyridyl rings were refined as rigid hexagons of 1.39 Å sides as attempts to restrain C—C and C—N distances to appropriate values require an excessive number of restraints. The Uij parameters of the primed atoms were set to those of the unprimed ones. Additionally, the anisotropic displacement parameters of the carbon atoms were tightly restrained so that they were almost nearly isotropic. The C21/C21' atoms have somewhat elongated thermal ellipsoids, which is probably a consequence of the disorder. More than two orientation of the disordered molecules are possible but splitting the molecules further did not yield more meaningful results.

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of 7C10H8N2.4C10H13N3O2S.2H2O at the 70% probability level; H atoms are drawn as spheres of arbitrary radius. Unlabeled atoms in N11-, N12- and N13-pyridine rings are related to other labeled atoms by the symmetry ...

Crystal data

7(C10H8N2)·4(C10H13N3O2S)·2(H2O)Z = 1
Mr = 2086.50F(000) = 1098
Triclinic, P1Dx = 1.325 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.7683 (3) ÅCell parameters from 3358 reflections
b = 15.2531 (4) Åθ = 2.6–26.0°
c = 16.0612 (4) ŵ = 0.16 mm1
α = 74.639 (2)°T = 153 K
β = 86.561 (2)°Plate, yellow
γ = 70.252 (1)°0.20 × 0.20 × 0.05 mm
V = 2615.2 (1) Å3

Data collection

Bruker SMART APEX diffractometer10042 independent reflections
Radiation source: fine-focus sealed tube6419 reflections with I > 2σ(I)
graphiteRint = 0.034
ω scansθmax = 26.0°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −14→15
Tmin = 0.968, Tmax = 0.992k = −19→19
18419 measured reflectionsl = −20→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H atoms treated by a mixture of independent and constrained refinement
S = 1.02w = 1/[σ2(Fo2) + (0.0783P)2 + 2.0276P] where P = (Fo2 + 2Fc2)/3
10042 reflections(Δ/σ)max = 0.001
686 parametersΔρmax = 0.66 e Å3
170 restraintsΔρmin = −0.56 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
S10.25549 (8)0.84394 (7)0.73613 (5)0.0403 (2)
S20.65813 (8)0.93784 (8)1.26910 (7)0.0511 (3)
O10.3505 (2)0.66350 (18)0.35305 (17)0.0458 (6)
H1O0.388 (4)0.645 (3)0.311 (2)0.081 (15)*
O2−0.0039 (2)0.74630 (19)0.17564 (17)0.0470 (6)
H2O0.045 (3)0.721 (3)0.141 (2)0.058 (12)*
O30.9220 (2)0.67293 (17)0.94434 (15)0.0396 (6)
H3O0.966 (4)0.644 (3)0.910 (3)0.100 (18)*
O40.6292 (2)0.70169 (17)0.73457 (14)0.0386 (5)
H4O0.693 (2)0.679 (3)0.710 (2)0.066 (13)*
O1w0.4655 (3)0.7058 (3)0.6093 (2)0.0781 (10)
H1w10.500 (4)0.716 (3)0.648 (2)0.078 (16)*
H1w20.509 (5)0.696 (5)0.567 (3)0.15 (3)*
N10.0466 (2)0.8843 (2)0.65301 (18)0.0353 (6)
H1N0.008 (3)0.877 (3)0.6112 (16)0.049 (11)*
N20.2186 (2)0.7963 (2)0.59750 (18)0.0352 (6)
H2N0.2980 (10)0.771 (2)0.602 (2)0.049 (11)*
N30.1528 (2)0.79739 (19)0.52915 (17)0.0349 (6)
N40.4992 (2)0.91841 (19)1.17051 (18)0.0343 (6)
H4N0.484 (3)0.904 (3)1.1236 (14)0.049 (11)*
N50.6981 (2)0.8472 (2)1.14649 (18)0.0381 (7)
H5N0.7738 (13)0.839 (2)1.158 (2)0.042 (10)*
N60.6625 (2)0.82602 (19)1.07669 (16)0.0328 (6)
C1−0.0538 (3)0.8798 (3)0.7937 (2)0.0504 (10)
H1A−0.09720.92120.83080.076*
H1B0.01960.83150.82440.076*
H1C−0.10570.84720.77910.076*
C2−0.0201 (3)0.9405 (2)0.7120 (2)0.0417 (8)
H2A−0.09470.98950.68180.050*
H2B0.02970.97510.72750.050*
C30.1660 (3)0.8421 (2)0.6589 (2)0.0313 (7)
C40.2164 (3)0.7593 (2)0.4716 (2)0.0343 (7)
H40.30180.73350.47910.041*
C50.1601 (3)0.7548 (2)0.3954 (2)0.0335 (7)
C60.2295 (3)0.7075 (2)0.3359 (2)0.0362 (8)
C70.1760 (3)0.7045 (2)0.2625 (2)0.0372 (8)
H70.22430.67240.22280.045*
C80.0531 (3)0.7478 (2)0.2469 (2)0.0369 (8)
C9−0.0184 (3)0.7960 (2)0.3044 (2)0.0382 (8)
H9−0.10300.82640.29380.046*
C100.0360 (3)0.7987 (2)0.3766 (2)0.0371 (8)
H10−0.01280.83180.41550.045*
C110.3731 (3)0.9035 (3)1.2993 (2)0.0487 (9)
H11A0.30460.94081.32740.073*
H11B0.44480.87701.33790.073*
H11C0.35420.85071.28620.073*
C120.3977 (3)0.9690 (2)1.2159 (2)0.0384 (8)
H12A0.32450.99651.17750.046*
H12B0.41471.02321.22940.046*
C130.6134 (3)0.9001 (2)1.1925 (2)0.0345 (7)
C140.7464 (3)0.7858 (2)1.0308 (2)0.0318 (7)
H140.82860.77071.04670.038*
C150.7159 (3)0.7632 (2)0.95436 (19)0.0287 (7)
C160.8071 (3)0.7075 (2)0.91068 (19)0.0291 (7)
C170.7786 (3)0.6880 (2)0.83663 (18)0.0302 (7)
H170.84080.65170.80650.036*
C180.6599 (3)0.7210 (2)0.80616 (18)0.0304 (7)
C190.5682 (3)0.7757 (2)0.8492 (2)0.0338 (7)
H190.48670.79870.82840.041*
C200.5975 (3)0.7958 (2)0.9220 (2)0.0322 (7)
H200.53490.83310.95120.039*
N70.1690 (5)0.6506 (5)0.0762 (5)0.0436 (9)0.50
C210.1857 (6)0.7027 (3)−0.0060 (5)0.0282 (14)0.50
H210.14370.7702−0.02440.034*0.50
C220.2638 (7)0.6562 (5)−0.0613 (4)0.0268 (14)0.50
H220.27520.6919−0.11750.032*0.50
C230.3253 (5)0.5576 (5)−0.0344 (3)0.0342 (9)0.50
C240.3086 (4)0.5054 (4)0.0478 (3)0.0374 (15)0.50
H240.35060.43800.06620.045*0.50
C250.2304 (5)0.5519 (4)0.1031 (3)0.0419 (15)0.50
H250.21900.51630.15920.050*0.50
N80.5283 (5)0.4168 (4)−0.2247 (4)0.0456 (8)0.50
C260.4775 (4)0.5168 (4)−0.2494 (3)0.0412 (15)0.50
H260.48970.5517−0.30570.049*0.50
C270.4088 (4)0.5656 (3)−0.1919 (3)0.0361 (13)0.50
H270.37410.6340−0.20880.043*0.50
C280.3910 (5)0.5145 (5)−0.1095 (3)0.0316 (9)0.50
C290.4417 (6)0.4146 (5)−0.0848 (4)0.0283 (14)0.50
H290.42950.3796−0.02850.034*0.50
C300.5104 (6)0.3657 (3)−0.1423 (5)0.0322 (15)0.50
H300.54510.2974−0.12540.039*0.50
N7'0.1582 (5)0.6579 (5)0.0664 (5)0.0436 (9)0.50
C21'0.2138 (7)0.7087 (4)0.0021 (6)0.0282 (14)0.50
H21'0.19890.7753−0.00390.034*0.50
C22'0.2911 (6)0.6620 (5)−0.0534 (4)0.0268 (14)0.50
H22'0.32910.6968−0.09740.032*0.50
C23'0.3129 (5)0.5645 (5)−0.0447 (4)0.0342 (9)0.50
C24'0.2574 (5)0.5137 (4)0.0196 (4)0.0374 (15)0.50
H24'0.27230.44710.02560.045*0.50
C25'0.1800 (4)0.5604 (4)0.0751 (3)0.0419 (15)0.50
H25'0.14200.52570.11910.050*0.50
N8'0.5377 (5)0.4119 (4)−0.2166 (5)0.0456 (8)0.50
C26'0.5311 (4)0.5056 (4)−0.2200 (3)0.0412 (15)0.50
H26'0.57190.5382−0.26340.049*0.50
C27'0.4648 (4)0.5514 (3)−0.1598 (3)0.0361 (13)0.50
H27'0.46030.6154−0.16210.043*0.50
C28'0.4051 (5)0.5037 (5)−0.0962 (3)0.0316 (9)0.50
C29'0.4117 (6)0.4101 (5)−0.0928 (4)0.0283 (14)0.50
H29'0.37090.3775−0.04930.034*0.50
C30'0.4780 (6)0.3642 (3)−0.1530 (5)0.0322 (15)0.50
H30'0.48250.3002−0.15070.039*0.50
N90.6183 (5)0.6645 (4)0.4755 (3)0.0440 (18)0.50
C310.6864 (5)0.7070 (3)0.4150 (4)0.0492 (17)0.50
H310.69030.76820.41520.059*0.50
C320.7489 (4)0.6601 (4)0.3542 (3)0.0398 (14)0.50
H320.79540.68920.31290.048*0.50
C330.7432 (5)0.5706 (4)0.3540 (4)0.0336 (12)0.50
C340.6751 (6)0.5281 (3)0.4145 (5)0.0395 (14)0.50
H340.67120.46690.41430.047*0.50
C350.6127 (5)0.5750 (4)0.4752 (4)0.0405 (16)0.50
H350.56610.54590.51660.049*0.50
N100.9335 (5)0.4261 (4)0.1649 (3)0.0391 (8)0.50
C360.8856 (5)0.5262 (4)0.1435 (3)0.0283 (14)0.50
H360.89500.56260.08710.034*0.50
C370.8241 (6)0.5732 (3)0.2045 (4)0.0303 (14)0.50
H370.79140.64160.18980.036*0.50
C380.8105 (5)0.5199 (3)0.2869 (4)0.0314 (10)0.50
C390.8583 (4)0.4198 (3)0.3084 (2)0.0367 (12)0.50
H390.84900.38340.36480.044*0.50
C400.9199 (4)0.3729 (3)0.2474 (3)0.0375 (12)0.50
H400.95260.30440.26210.045*0.50
N9'0.6010 (5)0.6323 (4)0.4845 (3)0.0440 (18)0.50
C31'0.6291 (5)0.6924 (3)0.4109 (4)0.0492 (17)0.50
H31'0.60670.75960.40570.059*0.50
C32'0.6898 (5)0.6541 (4)0.3448 (3)0.0398 (14)0.50
H32'0.70900.69520.29450.048*0.50
C33'0.7225 (6)0.5558 (4)0.3525 (4)0.0336 (12)0.50
C34'0.6944 (6)0.4957 (3)0.4261 (5)0.0395 (14)0.50
H34'0.71670.42850.43130.047*0.50
C35'0.6337 (6)0.5340 (3)0.4922 (4)0.0405 (16)0.50
H35'0.61450.49290.54250.049*0.50
N10'0.9211 (5)0.4325 (5)0.1540 (3)0.0391 (8)0.50
C36'0.9193 (5)0.5226 (4)0.1589 (3)0.0283 (14)0.50
H36'0.96240.55660.11870.034*0.50
C37'0.8547 (6)0.5630 (3)0.2227 (4)0.0303 (14)0.50
H37'0.85350.62460.22600.036*0.50
C38'0.7917 (5)0.5134 (4)0.2815 (4)0.0314 (10)0.50
C39'0.7934 (4)0.4233 (3)0.2767 (3)0.0367 (12)0.50
H39'0.75040.38940.31690.044*0.50
C40'0.8581 (4)0.3829 (3)0.2129 (3)0.0375 (12)0.50
H40'0.85930.32130.20960.045*0.50
N110.8292 (4)0.6185 (4)0.6505 (3)0.0392 (10)0.50
C410.9111 (4)0.6576 (3)0.6025 (3)0.0398 (12)0.50
H410.91740.71580.60920.048*0.50
C420.9836 (4)0.6115 (3)0.5446 (3)0.0398 (12)0.50
H421.03950.63820.51180.048*0.50
C430.9743 (5)0.5263 (3)0.5348 (3)0.0299 (11)0.50
C440.8924 (5)0.4872 (3)0.5828 (4)0.0270 (14)0.50
H440.88610.42900.57610.032*0.50
C450.8199 (5)0.5334 (4)0.6407 (3)0.0289 (14)0.50
H450.76400.50670.67350.035*0.50
N11'0.8058 (5)0.6149 (4)0.6454 (3)0.0392 (10)0.50
C41'0.8322 (4)0.6690 (3)0.5672 (3)0.0398 (12)0.50
H41'0.80130.73750.55350.048*0.50
C42'0.9038 (4)0.6229 (3)0.5089 (2)0.0398 (12)0.50
H42'0.92180.65990.45550.048*0.50
C43'0.9490 (5)0.5228 (3)0.5289 (3)0.0299 (11)0.50
C44'0.9227 (5)0.4687 (3)0.6071 (4)0.0270 (14)0.50
H44'0.95360.40020.62070.032*0.50
C45'0.8511 (5)0.5147 (4)0.6653 (3)0.0289 (14)0.50
H45'0.83300.47770.71880.035*0.50
N12−0.1892 (2)0.9088 (2)0.56896 (19)0.0413 (7)
C46−0.2279 (3)0.9691 (2)0.4914 (2)0.0421 (8)
H46−0.16950.98730.45380.050*
C47−0.3472 (3)1.0070 (2)0.4621 (2)0.0392 (8)
H47−0.36881.05040.40640.047*
C48−0.4356 (3)0.9812 (2)0.51455 (19)0.0306 (7)
C49−0.3957 (3)0.9185 (2)0.5956 (2)0.0389 (8)
H49−0.45180.89860.63440.047*
C50−0.2754 (3)0.8854 (2)0.6193 (2)0.0424 (8)
H50−0.25150.84310.67520.051*
N130.3191 (3)0.8864 (2)1.0389 (2)0.0523 (8)
C510.2705 (4)0.9350 (3)0.9600 (3)0.0574 (11)
H510.32370.93940.91350.069*
C520.1478 (3)0.9795 (3)0.9415 (2)0.0518 (10)
H520.11921.01200.88370.062*
C530.0666 (3)0.9762 (2)1.0080 (2)0.0371 (8)
C540.1158 (3)0.9245 (2)1.0897 (2)0.0417 (8)
H540.06470.91851.13740.050*
C550.2396 (3)0.8816 (3)1.1015 (2)0.0479 (9)
H550.27040.84621.15830.057*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0363 (5)0.0501 (5)0.0309 (4)−0.0126 (4)0.0032 (4)−0.0077 (4)
S20.0350 (5)0.0713 (7)0.0654 (6)−0.0167 (5)0.0108 (4)−0.0514 (6)
O10.0297 (13)0.0553 (15)0.0630 (17)−0.0139 (11)0.0150 (12)−0.0363 (14)
O20.0386 (14)0.0649 (17)0.0536 (16)−0.0230 (13)0.0166 (12)−0.0379 (14)
O30.0308 (13)0.0503 (14)0.0357 (13)−0.0050 (11)0.0080 (10)−0.0203 (11)
O40.0421 (14)0.0454 (14)0.0293 (12)−0.0104 (11)0.0074 (11)−0.0181 (11)
O1w0.0499 (17)0.119 (3)0.0486 (17)0.0148 (16)−0.0045 (14)−0.0489 (18)
N10.0298 (15)0.0382 (15)0.0381 (16)−0.0083 (12)0.0068 (12)−0.0155 (13)
N20.0273 (15)0.0398 (16)0.0415 (16)−0.0101 (13)0.0082 (13)−0.0184 (13)
N30.0344 (15)0.0342 (15)0.0413 (16)−0.0155 (12)0.0108 (13)−0.0152 (12)
N40.0313 (15)0.0362 (15)0.0380 (16)−0.0069 (12)0.0050 (12)−0.0202 (13)
N50.0276 (15)0.0537 (18)0.0433 (16)−0.0146 (14)0.0090 (13)−0.0302 (14)
N60.0349 (15)0.0376 (15)0.0318 (14)−0.0140 (12)0.0082 (12)−0.0180 (12)
C10.049 (2)0.050 (2)0.056 (2)−0.0161 (18)0.0219 (19)−0.0252 (19)
C20.0370 (19)0.0362 (18)0.053 (2)−0.0072 (15)0.0079 (16)−0.0210 (16)
C30.0333 (17)0.0275 (16)0.0330 (17)−0.0116 (13)0.0083 (14)−0.0077 (13)
C40.0281 (16)0.0324 (17)0.0469 (19)−0.0127 (14)0.0117 (15)−0.0165 (15)
C50.0312 (17)0.0316 (16)0.0450 (19)−0.0164 (14)0.0145 (15)−0.0169 (15)
C60.0297 (17)0.0357 (18)0.054 (2)−0.0185 (14)0.0170 (15)−0.0222 (16)
C70.0340 (18)0.0379 (18)0.052 (2)−0.0184 (15)0.0189 (16)−0.0266 (16)
C80.0322 (18)0.0412 (19)0.049 (2)−0.0210 (15)0.0143 (15)−0.0221 (16)
C90.0296 (17)0.0421 (19)0.050 (2)−0.0160 (15)0.0116 (15)−0.0213 (16)
C100.0342 (18)0.0355 (18)0.049 (2)−0.0144 (15)0.0177 (15)−0.0229 (16)
C110.044 (2)0.054 (2)0.054 (2)−0.0196 (18)0.0175 (18)−0.0236 (19)
C120.0279 (17)0.0398 (19)0.047 (2)−0.0040 (14)0.0074 (15)−0.0218 (16)
C130.0311 (18)0.0344 (17)0.0412 (18)−0.0124 (14)0.0120 (14)−0.0157 (15)
C140.0295 (16)0.0340 (17)0.0360 (17)−0.0129 (14)0.0096 (14)−0.0146 (14)
C150.0322 (17)0.0278 (15)0.0276 (16)−0.0114 (13)0.0086 (13)−0.0096 (13)
C160.0280 (16)0.0273 (15)0.0298 (16)−0.0087 (13)0.0087 (13)−0.0063 (13)
C170.0347 (17)0.0282 (16)0.0251 (16)−0.0073 (13)0.0108 (13)−0.0089 (13)
C180.0398 (18)0.0288 (16)0.0223 (15)−0.0128 (14)0.0074 (13)−0.0059 (13)
C190.0321 (17)0.0368 (18)0.0304 (17)−0.0095 (14)0.0037 (14)−0.0084 (14)
C200.0332 (17)0.0287 (16)0.0320 (17)−0.0060 (13)0.0102 (14)−0.0114 (13)
N70.0465 (19)0.051 (2)0.040 (2)−0.0195 (16)0.0131 (16)−0.0216 (17)
C210.029 (3)0.0387 (19)0.031 (2)−0.0195 (18)−0.007 (2)−0.0192 (16)
C220.029 (3)0.0328 (18)0.0305 (19)−0.0228 (19)0.000 (2)−0.0115 (16)
C230.0334 (19)0.0347 (18)0.037 (2)−0.0138 (15)0.0092 (16)−0.0115 (16)
C240.038 (3)0.036 (2)0.038 (3)−0.012 (2)0.009 (2)−0.010 (2)
C250.039 (3)0.049 (2)0.041 (3)−0.020 (3)0.008 (2)−0.011 (2)
N80.0305 (17)0.0496 (19)0.059 (2)−0.0095 (14)0.0123 (15)−0.0260 (17)
C260.035 (3)0.050 (2)0.046 (3)−0.019 (3)0.014 (2)−0.020 (2)
C270.036 (3)0.035 (2)0.039 (3)−0.013 (2)0.009 (2)−0.011 (2)
C280.0282 (19)0.031 (2)0.034 (2)−0.0096 (16)0.0049 (16)−0.0064 (17)
C290.022 (3)0.0336 (18)0.0334 (19)−0.0144 (19)−0.004 (2)−0.0079 (16)
C300.021 (4)0.0358 (18)0.043 (3)−0.0053 (18)−0.012 (2)−0.0167 (17)
N7'0.0465 (19)0.051 (2)0.040 (2)−0.0195 (16)0.0131 (16)−0.0216 (17)
C21'0.029 (3)0.0387 (19)0.031 (2)−0.0195 (18)−0.007 (2)−0.0192 (16)
C22'0.029 (3)0.0328 (18)0.0305 (19)−0.0228 (19)0.000 (2)−0.0115 (16)
C23'0.0334 (19)0.0347 (18)0.037 (2)−0.0138 (15)0.0092 (16)−0.0115 (16)
C24'0.038 (3)0.036 (2)0.038 (3)−0.012 (2)0.009 (2)−0.010 (2)
C25'0.039 (3)0.049 (2)0.041 (3)−0.020 (3)0.008 (2)−0.011 (2)
N8'0.0305 (17)0.0496 (19)0.059 (2)−0.0095 (14)0.0123 (15)−0.0260 (17)
C26'0.035 (3)0.050 (2)0.046 (3)−0.019 (3)0.014 (2)−0.020 (2)
C27'0.036 (3)0.035 (2)0.039 (3)−0.013 (2)0.009 (2)−0.011 (2)
C28'0.0282 (19)0.031 (2)0.034 (2)−0.0096 (16)0.0049 (16)−0.0064 (17)
C29'0.022 (3)0.0336 (18)0.0334 (19)−0.0144 (19)−0.004 (2)−0.0079 (16)
C30'0.021 (4)0.0358 (18)0.043 (3)−0.0053 (18)−0.012 (2)−0.0167 (17)
N90.040 (3)0.050 (5)0.037 (2)−0.005 (3)0.0048 (17)−0.017 (3)
C310.053 (4)0.046 (3)0.040 (2)−0.002 (3)0.000 (3)−0.017 (2)
C320.044 (4)0.036 (2)0.034 (2)−0.006 (2)0.005 (3)−0.0093 (18)
C330.031 (2)0.034 (2)0.0305 (16)−0.0044 (16)0.0036 (16)−0.0078 (15)
C340.038 (3)0.041 (3)0.036 (2)−0.008 (3)0.009 (2)−0.012 (3)
C350.035 (3)0.044 (4)0.037 (3)−0.006 (3)0.005 (2)−0.012 (3)
N100.0273 (17)0.0492 (19)0.0391 (18)−0.0054 (14)0.0060 (14)−0.0194 (16)
C360.014 (3)0.043 (2)0.026 (2)−0.006 (2)−0.008 (2)−0.0083 (18)
C370.025 (3)0.0354 (19)0.027 (3)−0.0045 (19)−0.005 (2)−0.0084 (18)
C380.028 (2)0.0308 (18)0.0309 (18)−0.0036 (16)0.0038 (16)−0.0097 (15)
C390.038 (3)0.037 (2)0.035 (2)−0.012 (2)0.0079 (19)−0.0095 (18)
C400.037 (3)0.036 (2)0.038 (3)−0.007 (2)0.002 (2)−0.015 (2)
N9'0.040 (3)0.050 (5)0.037 (2)−0.005 (3)0.0048 (17)−0.017 (3)
C31'0.053 (4)0.046 (3)0.040 (2)−0.002 (3)0.000 (3)−0.017 (2)
C32'0.044 (4)0.036 (2)0.034 (2)−0.006 (2)0.005 (3)−0.0093 (18)
C33'0.031 (2)0.034 (2)0.0305 (16)−0.0044 (16)0.0036 (16)−0.0078 (15)
C34'0.038 (3)0.041 (3)0.036 (2)−0.008 (3)0.009 (2)−0.012 (3)
C35'0.035 (3)0.044 (4)0.037 (3)−0.006 (3)0.005 (2)−0.012 (3)
N10'0.0273 (17)0.0492 (19)0.0391 (18)−0.0054 (14)0.0060 (14)−0.0194 (16)
C36'0.014 (3)0.043 (2)0.026 (2)−0.006 (2)−0.008 (2)−0.0083 (18)
C37'0.025 (3)0.0354 (19)0.027 (3)−0.0045 (19)−0.005 (2)−0.0084 (18)
C38'0.028 (2)0.0308 (18)0.0309 (18)−0.0036 (16)0.0038 (16)−0.0097 (15)
C39'0.038 (3)0.037 (2)0.035 (2)−0.012 (2)0.0079 (19)−0.0095 (18)
C40'0.037 (3)0.036 (2)0.038 (3)−0.007 (2)0.002 (2)−0.015 (2)
N110.039 (2)0.0432 (18)0.0345 (16)−0.0080 (16)0.0083 (16)−0.0186 (14)
C410.048 (3)0.038 (2)0.037 (3)−0.012 (2)0.004 (2)−0.018 (2)
C420.042 (3)0.035 (2)0.040 (3)−0.011 (2)0.015 (2)−0.011 (2)
C430.034 (3)0.0284 (17)0.0249 (17)−0.0060 (17)0.0060 (18)−0.0089 (14)
C440.026 (3)0.031 (2)0.022 (3)−0.007 (2)−0.002 (2)−0.007 (2)
C450.024 (3)0.040 (3)0.019 (3)−0.006 (2)−0.005 (2)−0.007 (2)
N11'0.039 (2)0.0432 (18)0.0345 (16)−0.0080 (16)0.0083 (16)−0.0186 (14)
C41'0.048 (3)0.038 (2)0.037 (3)−0.012 (2)0.004 (2)−0.018 (2)
C42'0.042 (3)0.035 (2)0.040 (3)−0.011 (2)0.015 (2)−0.011 (2)
C43'0.034 (3)0.0284 (17)0.0249 (17)−0.0060 (17)0.0060 (18)−0.0089 (14)
C44'0.026 (3)0.031 (2)0.022 (3)−0.007 (2)−0.002 (2)−0.007 (2)
C45'0.024 (3)0.040 (3)0.019 (3)−0.006 (2)−0.005 (2)−0.007 (2)
N120.0373 (16)0.0340 (15)0.0480 (17)−0.0078 (13)0.0078 (13)−0.0100 (14)
C460.040 (2)0.0369 (19)0.046 (2)−0.0140 (16)0.0115 (16)−0.0058 (16)
C470.0399 (19)0.0386 (19)0.0350 (18)−0.0133 (15)0.0096 (15)−0.0046 (15)
C480.0381 (17)0.0237 (15)0.0291 (16)−0.0082 (13)0.0102 (14)−0.0101 (13)
C490.040 (2)0.0306 (17)0.0397 (19)−0.0101 (15)0.0097 (15)−0.0031 (15)
C500.045 (2)0.0338 (18)0.0377 (19)−0.0054 (16)0.0063 (16)−0.0023 (15)
N130.0445 (18)0.0436 (18)0.058 (2)−0.0058 (15)−0.0058 (16)−0.0050 (16)
C510.047 (2)0.049 (2)0.059 (3)−0.0063 (19)0.009 (2)−0.002 (2)
C520.048 (2)0.048 (2)0.042 (2)−0.0030 (18)−0.0010 (17)−0.0004 (17)
C530.0438 (19)0.0246 (16)0.0378 (18)−0.0048 (14)−0.0017 (15)−0.0076 (14)
C540.045 (2)0.0373 (19)0.0386 (19)−0.0060 (16)0.0005 (16)−0.0135 (16)
C550.051 (2)0.043 (2)0.042 (2)−0.0086 (18)−0.0096 (18)−0.0064 (17)

Geometric parameters (Å, °)

S1—C31.686 (3)C26'—C27'1.39
S2—C131.667 (3)C26'—H26'0.95
O1—C61.363 (4)C27'—C28'1.39
O1—H1O0.84 (4)C27'—H27'0.95
O2—C81.370 (4)C28'—C29'1.39
O2—H2O0.84 (4)C29'—C30'1.39
O3—C161.361 (4)C29'—H29'0.95
O3—H3O0.84 (4)C30'—H30'0.95
O4—C181.357 (4)N9—C311.39
O4—H4O0.84 (4)N9—C351.39
O1w—H1w10.84 (3)C31—C321.39
O1w—H1w20.84 (3)C31—H310.95
N1—C31.331 (4)C32—C331.39
N1—C21.461 (4)C32—H320.95
N1—H1N0.88 (3)C33—C341.39
N2—C31.357 (4)C33—C381.520 (5)
N2—N31.374 (4)C34—C351.39
N2—H2N0.88 (3)C34—H340.95
N3—C41.288 (4)C35—H350.95
N4—C131.327 (4)N10—C361.39
N4—C121.458 (4)N10—C401.39
N4—H4N0.88 (3)C36—C371.39
N5—C131.369 (4)C36—H360.95
N5—N61.370 (4)C37—C381.39
N5—H5N0.88 (3)C37—H370.95
N6—C141.280 (4)C38—C391.39
C1—C21.510 (5)C39—C401.39
C1—H1A0.98C39—H390.95
C1—H1B0.98C40—H400.95
C1—H1C0.98N9'—C31'1.39
C2—H2A0.99N9'—C35'1.39
C2—H2B0.99C31'—C32'1.39
C4—C51.454 (5)C31'—H31'0.95
C4—H40.95C32'—C33'1.39
C5—C101.398 (5)C32'—H32'0.95
C5—C61.405 (4)C33'—C34'1.39
C6—C71.388 (5)C33'—C38'1.517 (5)
C7—C81.379 (4)C34'—C35'1.39
C7—H70.95C34'—H34'0.95
C8—C91.396 (4)C35'—H35'0.95
C9—C101.375 (5)N10'—C36'1.39
C9—H90.95N10'—C40'1.39
C10—H100.95C36'—C37'1.39
C11—C121.521 (5)C36'—H36'0.95
C11—H11A0.98C37'—C38'1.39
C11—H11B0.98C37'—H37'0.95
C11—H11C0.98C38'—C39'1.39
C12—H12A0.99C39'—C40'1.39
C12—H12B0.99C39'—H39'0.95
C14—C151.455 (4)C40'—H40'0.95
C14—H140.95N11—C411.39
C15—C201.393 (4)N11—C451.39
C15—C161.405 (4)C41—C421.39
C16—C171.385 (4)C41—H410.95
C17—C181.385 (4)C42—C431.39
C17—H170.95C42—H420.95
C18—C191.395 (4)C43—C441.39
C19—C201.376 (4)C43—C43i1.525 (8)
C19—H190.95C44—C451.39
C20—H200.95C44—H440.95
N7—C211.39C45—H450.95
N7—C251.39N11'—C41'1.39
C21—C221.39N11'—C45'1.39
C21—H210.95C41'—C42'1.39
C22—C231.39C41'—H41'0.95
C22—H220.95C42'—C43'1.39
C23—C241.39C42'—H42'0.95
C23—C281.565 (6)C43'—C44'1.39
C24—C251.39C43'—C43'i1.558 (8)
C24—H240.95C44'—C45'1.39
C25—H250.95C44'—H44'0.95
N8—C261.39C45'—H45'0.95
N8—C301.39N12—C461.336 (4)
C26—C271.39N12—C501.343 (4)
C26—H260.95C46—C471.384 (5)
C27—C281.39C46—H460.95
C27—H270.95C47—C481.394 (4)
C28—C291.39C47—H470.95
C29—C301.39C48—C491.392 (4)
C29—H290.95C48—C48ii1.484 (6)
C30—H300.95C49—C501.373 (5)
N7'—C21'1.39C49—H490.95
N7'—C25'1.39C50—H500.95
C21'—C22'1.39N13—C511.335 (5)
C21'—H21'0.95N13—C551.337 (5)
C22'—C23'1.39C51—C521.384 (5)
C22'—H22'0.95C51—H510.95
C23'—C24'1.39C52—C531.392 (5)
C23'—C28'1.530 (6)C52—H520.95
C24'—C25'1.39C53—C541.383 (5)
C24'—H24'0.95C53—C53iii1.494 (7)
C25'—H25'0.95C54—C551.381 (5)
N8'—C26'1.39C54—H540.95
N8'—C30'1.39C55—H550.95
C6—O1—H1O113 (3)N8'—C26'—H26'120.0
C8—O2—H2O113 (3)C26'—C27'—C28'120.0
C16—O3—H3O106 (4)C26'—C27'—H27'120.0
C18—O4—H4O108 (3)C28'—C27'—H27'120.0
H1w1—O1w—H1w2114 (5)C29'—C28'—C27'120.0
C3—N1—C2122.8 (3)C29'—C28'—C23'121.6 (5)
C3—N1—H1N117 (2)C27'—C28'—C23'117.1 (5)
C2—N1—H1N120 (2)C28'—C29'—C30'120.0
C3—N2—N3121.8 (3)C28'—C29'—H29'120.0
C3—N2—H2N115 (2)C30'—C29'—H29'120.0
N3—N2—H2N123 (2)C29'—C30'—N8'120.0
C4—N3—N2114.8 (3)C29'—C30'—H30'120.0
C13—N4—C12122.8 (3)N8'—C30'—H30'120.0
C13—N4—H4N119 (2)C31—N9—C35120.0
C12—N4—H4N118 (2)C32—C31—N9120.0
C13—N5—N6119.8 (3)C32—C31—H31120.0
C13—N5—H5N116 (2)N9—C31—H31120.0
N6—N5—H5N123 (2)C31—C32—C33120.0
C14—N6—N5116.7 (3)C31—C32—H32120.0
C2—C1—H1A109.5C33—C32—H32120.0
C2—C1—H1B109.5C32—C33—C34120.0
H1A—C1—H1B109.5C32—C33—C38119.9 (4)
C2—C1—H1C109.5C34—C33—C38120.1 (4)
H1A—C1—H1C109.5C33—C34—C35120.0
H1B—C1—H1C109.5C33—C34—H34120.0
N1—C2—C1113.3 (3)C35—C34—H34120.0
N1—C2—H2A108.9C34—C35—N9120.0
C1—C2—H2A108.9C34—C35—H35120.0
N1—C2—H2B108.9N9—C35—H35120.0
C1—C2—H2B108.9C36—N10—C40120.0
H2A—C2—H2B107.7N10—C36—C37120.0
N1—C3—N2117.4 (3)N10—C36—H36120.0
N1—C3—S1124.2 (2)C37—C36—H36120.0
N2—C3—S1118.4 (2)C36—C37—C38120.0
N3—C4—C5121.4 (3)C36—C37—H37120.0
N3—C4—H4119.3C38—C37—H37120.0
C5—C4—H4119.3C39—C38—C37120.0
C10—C5—C6116.9 (3)C39—C38—C33119.7 (4)
C10—C5—C4122.2 (3)C37—C38—C33120.3 (4)
C6—C5—C4120.9 (3)C38—C39—C40120.0
O1—C6—C7121.0 (3)C38—C39—H39120.0
O1—C6—C5118.1 (3)C40—C39—H39120.0
C7—C6—C5120.9 (3)C39—C40—N10120.0
C8—C7—C6120.3 (3)C39—C40—H40120.0
C8—C7—H7119.9N10—C40—H40120.0
C6—C7—H7119.9C31'—N9'—C35'120.0
O2—C8—C7122.4 (3)C32'—C31'—N9'120.0
O2—C8—C9117.3 (3)C32'—C31'—H31'120.0
C7—C8—C9120.3 (3)N9'—C31'—H31'120.0
C10—C9—C8118.7 (3)C31'—C32'—C33'120.0
C10—C9—H9120.6C31'—C32'—H32'120.0
C8—C9—H9120.6C33'—C32'—H32'120.0
C9—C10—C5122.9 (3)C32'—C33'—C34'120.0
C9—C10—H10118.6C32'—C33'—C38'120.1 (4)
C5—C10—H10118.6C34'—C33'—C38'119.9 (4)
C12—C11—H11A109.5C35'—C34'—C33'120.0
C12—C11—H11B109.5C35'—C34'—H34'120.0
H11A—C11—H11B109.5C33'—C34'—H34'120.0
C12—C11—H11C109.5C34'—C35'—N9'120.0
H11A—C11—H11C109.5C34'—C35'—H35'120.0
H11B—C11—H11C109.5N9'—C35'—H35'120.0
N4—C12—C11112.5 (3)C36'—N10'—C40'120.0
N4—C12—H12A109.1N10'—C36'—C37'120.0
C11—C12—H12A109.1N10'—C36'—H36'120.0
N4—C12—H12B109.1C37'—C36'—H36'120.0
C11—C12—H12B109.1C38'—C37'—C36'120.0
H12A—C12—H12B107.8C38'—C37'—H37'120.0
N4—C13—N5115.5 (3)C36'—C37'—H37'120.0
N4—C13—S2124.9 (2)C37'—C38'—C39'120.0
N5—C13—S2119.5 (2)C37'—C38'—C33'120.6 (4)
N6—C14—C15120.0 (3)C39'—C38'—C33'119.4 (4)
N6—C14—H14120.0C40'—C39'—C38'120.0
C15—C14—H14120.0C40'—C39'—H39'120.0
C20—C15—C16118.2 (3)C38'—C39'—H39'120.0
C20—C15—C14121.8 (3)C39'—C40'—N10'120.0
C16—C15—C14120.1 (3)C39'—C40'—H40'120.0
O3—C16—C17122.0 (3)N10'—C40'—H40'120.0
O3—C16—C15117.9 (3)C41—N11—C45120.0
C17—C16—C15120.1 (3)N11—C41—C42120.0
C16—C17—C18120.5 (3)N11—C41—H41120.0
C16—C17—H17119.8C42—C41—H41120.0
C18—C17—H17119.8C41—C42—C43120.0
O4—C18—C17121.7 (3)C41—C42—H42120.0
O4—C18—C19118.1 (3)C43—C42—H42120.0
C17—C18—C19120.2 (3)C44—C43—C42120.0
C20—C19—C18119.0 (3)C44—C43—C43i109.9 (7)
C20—C19—H19120.5C42—C43—C43i129.1 (7)
C18—C19—H19120.5C45—C44—C43120.0
C19—C20—C15122.1 (3)C45—C44—H44120.0
C19—C20—H20118.9C43—C44—H44120.0
C15—C20—H20118.9C44—C45—N11120.0
C21—N7—C25120.0C44—C45—H45120.0
N7—C21—C22120.0N11—C45—H45120.0
N7—C21—H21120.0C41'—N11'—C45'120.0
C22—C21—H21120.0C42'—C41'—N11'120.0
C21—C22—C23120.0C42'—C41'—H41'120.0
C21—C22—H22120.0N11'—C41'—H41'120.0
C23—C22—H22120.0C41'—C42'—C43'120.0
C24—C23—C22120.0C41'—C42'—H42'120.0
C24—C23—C28126.3 (5)C43'—C42'—H42'120.0
C22—C23—C28112.9 (5)C42'—C43'—C44'120.0
C25—C24—C23120.0C42'—C43'—C43'i116.6 (6)
C25—C24—H24120.0C44'—C43'—C43'i122.0 (6)
C23—C24—H24120.0C43'—C44'—C45'120.0
C24—C25—N7120.0C43'—C44'—H44'120.0
C24—C25—H25120.0C45'—C44'—H44'120.0
N7—C25—H25120.0C44'—C45'—N11'120.0
C26—N8—C30120.0C44'—C45'—H45'120.0
C27—C26—N8120.0N11'—C45'—H45'120.0
C27—C26—H26120.0C46—N12—C50115.3 (3)
N8—C26—H26120.0N12—C46—C47124.4 (3)
C26—C27—C28120.0N12—C46—H46117.8
C26—C27—H27120.0C47—C46—H46117.8
C28—C27—H27120.0C46—C47—C48119.7 (3)
C29—C28—C27120.0C46—C47—H47120.1
C29—C28—C23112.9 (5)C48—C47—H47120.1
C27—C28—C23126.9 (5)C49—C48—C47116.0 (3)
C28—C29—C30120.0C49—C48—C48ii122.3 (3)
C28—C29—H29120.0C47—C48—C48ii121.7 (3)
C30—C29—H29120.0C50—C49—C48120.0 (3)
C29—C30—N8120.0C50—C49—H49120.0
C29—C30—H30120.0C48—C49—H49120.0
N8—C30—H30120.0N12—C50—C49124.5 (3)
C21'—N7'—C25'120.0N12—C50—H50117.7
C22'—C21'—N7'120.0C49—C50—H50117.7
C22'—C21'—H21'120.0C51—N13—C55115.0 (3)
N7'—C21'—H21'120.0N13—C51—C52124.5 (4)
C21'—C22'—C23'120.0N13—C51—H51117.7
C21'—C22'—H22'120.0C52—C51—H51117.7
C23'—C22'—H22'120.0C51—C52—C53119.7 (3)
C24'—C23'—C22'120.0C51—C52—H52120.2
C24'—C23'—C28'115.3 (5)C53—C52—H52120.2
C22'—C23'—C28'124.5 (5)C54—C53—C52116.3 (3)
C23'—C24'—C25'120.0C54—C53—C53iii121.7 (4)
C23'—C24'—H24'120.0C52—C53—C53iii122.0 (4)
C25'—C24'—H24'120.0C55—C54—C53119.7 (3)
C24'—C25'—N7'120.0C55—C54—H54120.2
C24'—C25'—H25'120.0C53—C54—H54120.2
N7'—C25'—H25'120.0N13—C55—C54124.8 (3)
C26'—N8'—C30'120.0N13—C55—H55117.6
C27'—C26'—N8'120.0C54—C55—H55117.6
C27'—C26'—H26'120.0
C3—N2—N3—C4173.4 (3)C24'—C23'—C28'—C27'−178.5 (3)
C13—N5—N6—C14172.5 (3)C22'—C23'—C28'—C27'−4.4 (6)
C3—N1—C2—C1−86.2 (4)C27'—C28'—C29'—C30'0.0
C2—N1—C3—N2−176.4 (3)C23'—C28'—C29'—C30'166.7 (6)
C2—N1—C3—S12.2 (4)C28'—C29'—C30'—N8'0.0
N3—N2—C3—N13.3 (4)C26'—N8'—C30'—C29'0.0
N3—N2—C3—S1−175.4 (2)C35—N9—C31—C320.0
N2—N3—C4—C5180.0 (3)N9—C31—C32—C330.0
N3—C4—C5—C105.7 (5)C31—C32—C33—C340.0
N3—C4—C5—C6−175.8 (3)C31—C32—C33—C38179.4 (6)
C10—C5—C6—O1−179.5 (3)C32—C33—C34—C350.0
C4—C5—C6—O11.9 (4)C38—C33—C34—C35−179.4 (6)
C10—C5—C6—C7−0.4 (5)C33—C34—C35—N90.0
C4—C5—C6—C7−179.0 (3)C31—N9—C35—C340.0
O1—C6—C7—C8178.8 (3)C40—N10—C36—C370.0
C5—C6—C7—C8−0.2 (5)N10—C36—C37—C380.0
C6—C7—C8—O2−179.6 (3)C36—C37—C38—C390.0
C6—C7—C8—C90.7 (5)C36—C37—C38—C33−179.9 (6)
O2—C8—C9—C10179.9 (3)C32—C33—C38—C39146.9 (4)
C7—C8—C9—C10−0.4 (5)C34—C33—C38—C39−33.7 (6)
C8—C9—C10—C5−0.3 (5)C32—C33—C38—C37−33.2 (6)
C6—C5—C10—C90.7 (5)C34—C33—C38—C37146.2 (3)
C4—C5—C10—C9179.3 (3)C37—C38—C39—C400.0
C13—N4—C12—C11−80.2 (4)C33—C38—C39—C40179.9 (6)
C12—N4—C13—N5176.5 (3)C38—C39—C40—N100.0
C12—N4—C13—S2−4.5 (5)C36—N10—C40—C390.0
N6—N5—C13—N47.0 (4)C35'—N9'—C31'—C32'0.0
N6—N5—C13—S2−172.1 (2)N9'—C31'—C32'—C33'0.0
N5—N6—C14—C15−178.4 (3)C31'—C32'—C33'—C34'0.0
N6—C14—C15—C209.0 (5)C31'—C32'—C33'—C38'−178.4 (6)
N6—C14—C15—C16−171.3 (3)C32'—C33'—C34'—C35'0.0
C20—C15—C16—O3−177.7 (3)C38'—C33'—C34'—C35'178.4 (6)
C14—C15—C16—O32.7 (4)C33'—C34'—C35'—N9'0.0
C20—C15—C16—C171.3 (4)C31'—N9'—C35'—C34'0.0
C14—C15—C16—C17−178.4 (3)C40'—N10'—C36'—C37'0.0
O3—C16—C17—C18177.3 (3)N10'—C36'—C37'—C38'0.0
C15—C16—C17—C18−1.6 (4)C36'—C37'—C38'—C39'0.0
C16—C17—C18—O4−179.0 (3)C36'—C37'—C38'—C33'178.9 (6)
C16—C17—C18—C191.0 (4)C32'—C33'—C38'—C37'19.7 (7)
O4—C18—C19—C20179.8 (3)C34'—C33'—C38'—C37'−158.7 (3)
C17—C18—C19—C20−0.2 (4)C32'—C33'—C38'—C39'−161.4 (4)
C18—C19—C20—C15−0.1 (5)C34'—C33'—C38'—C39'20.3 (6)
C16—C15—C20—C19−0.4 (4)C37'—C38'—C39'—C40'0.0
C14—C15—C20—C19179.2 (3)C33'—C38'—C39'—C40'−178.9 (6)
C25—N7—C21—C220.0C38'—C39'—C40'—N10'0.0
N7—C21—C22—C230.0C36'—N10'—C40'—C39'0.0
C21—C22—C23—C240.0C45—N11—C41—C420.0
C21—C22—C23—C28170.0 (5)N11—C41—C42—C430.0
C22—C23—C24—C250.0C41—C42—C43—C440.0
C28—C23—C24—C25−168.5 (6)C41—C42—C43—C43i167.5 (10)
C23—C24—C25—N70.0C42—C43—C44—C450.0
C21—N7—C25—C240.0C43i—C43—C44—C45−169.7 (8)
C30—N8—C26—C270.0C43—C44—C45—N110.0
N8—C26—C27—C280.0C41—N11—C45—C440.0
C26—C27—C28—C290.0C45'—N11'—C41'—C42'0.0
C26—C27—C28—C23174.9 (6)N11'—C41'—C42'—C43'0.0
C24—C23—C28—C29−4.5 (6)C41'—C42'—C43'—C44'0.0
C22—C23—C28—C29−173.7 (3)C41'—C42'—C43'—C43'i−166.4 (9)
C24—C23—C28—C27−179.7 (3)C42'—C43'—C44'—C45'0.0
C22—C23—C28—C2711.1 (6)C43'i—C43'—C44'—C45'165.6 (10)
C27—C28—C29—C300.0C43'—C44'—C45'—N11'0.0
C23—C28—C29—C30−175.6 (5)C41'—N11'—C45'—C44'0.0
C28—C29—C30—N80.0C50—N12—C46—C470.1 (5)
C26—N8—C30—C290.0N12—C46—C47—C48−0.9 (5)
C25'—N7'—C21'—C22'0.0C46—C47—C48—C491.0 (5)
N7'—C21'—C22'—C23'0.0C46—C47—C48—C48ii−179.2 (4)
C21'—C22'—C23'—C24'0.0C47—C48—C49—C50−0.4 (5)
C21'—C22'—C23'—C28'−173.9 (6)C48ii—C48—C49—C50179.8 (4)
C22'—C23'—C24'—C25'0.0C46—N12—C50—C490.5 (5)
C28'—C23'—C24'—C25'174.5 (5)C48—C49—C50—N12−0.4 (5)
C23'—C24'—C25'—N7'0.0C55—N13—C51—C520.8 (6)
C21'—N7'—C25'—C24'0.0N13—C51—C52—C531.1 (7)
C30'—N8'—C26'—C27'0.0C51—C52—C53—C54−2.2 (5)
N8'—C26'—C27'—C28'0.0C51—C52—C53—C53iii179.3 (4)
C26'—C27'—C28'—C29'0.0C52—C53—C54—C551.4 (5)
C26'—C27'—C28'—C23'−167.3 (5)C53iii—C53—C54—C55179.9 (4)
C24'—C23'—C28'—C29'14.4 (6)C51—N13—C55—C54−1.7 (6)
C22'—C23'—C28'—C29'−171.4 (4)C53—C54—C55—N130.5 (6)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x−1, −y+2, −z+1; (iii) −x, −y+2, −z+2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1o···N8iv0.84 (4)1.92 (1)2.755 (5)171 (5)
O1—H1o···N8'iv0.84 (4)1.97 (1)2.798 (5)171 (5)
O2—H2o···N70.84 (4)1.93 (1)2.768 (5)172 (4)
O2—H2o···N7'0.84 (4)1.93 (1)2.766 (5)178 (4)
O3—H3o···N10i0.84 (4)1.91 (1)2.751 (5)178 (5)
O3—H3o···N10'i0.84 (4)1.90 (1)2.736 (5)172 (5)
O4—H4o···N110.84 (4)1.90 (1)2.735 (4)174 (4)
O1w—H1w1···O40.84 (3)2.04 (2)2.843 (4)160 (5)
O1w—H1w2···N90.84 (3)1.94 (1)2.782 (5)175 (7)
O1w—H1w2···N9'0.84 (3)1.91 (3)2.722 (5)160 (7)
N1—H1n···N120.88 (3)2.31 (3)3.024 (4)138 (3)
N2—H2n···O1w0.88 (3)1.88 (1)2.757 (4)175 (4)
N4—H4n···N130.88 (3)2.56 (2)3.315 (4)144 (3)
N5—H5n···O2v0.88 (1)2.51 (2)3.325 (4)155 (3)

Symmetry codes: (iv) −x+1, −y+1, −z; (i) −x+2, −y+1, −z+1; (v) x+1, y, z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2864).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Lavender, E. S., Ferguson, G. & Glidewell, C. (1999). Acta Cryst. C55, 430–432.
  • Oswald, I. D. H., Motherwell, W. D. S. & Parsons, S. (2005). Acta Cryst. B61, 46–57. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tan, K. W., Ng, C. H., Maah, M. J. & Ng, S. W. (2008). Acta Cryst. E64, o2123. [PMC free article] [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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