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Acta Cryst. (2009). E65, o2129    [ doi:10.1107/S1600536809030852 ]

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

S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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 operation (2 - x, 1 - y, 1 - z), (-x - 1, 2 - y, 1 - z) and (-x, 2 - y, 2 - z), respectively. Only one component of the disordered molecules are shown.
(E)-2,4-Dihydroxybenzaldehyde 4-ethylthiosemicarbazone– 4,4'-bipyridine–water (4/7/2) top
Crystal data top
7(C10H8N2)·4(C10H13N3O2S)·2(H2O)Z = 1
Mr = 2086.50F(000) = 1098
Triclinic, P1Dx = 1.325 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		10042 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 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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 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 Å−3
170 restraintsΔρmin = −0.56 e Å−3
Crystal data top
7(C10H8N2)·4(C10H13N3O2S)·2(H2O)γ = 70.252 (1)°
Mr = 2086.50V = 2615.2 (1) Å3
Triclinic, P1Z = 1
a = 11.7683 (3) ÅMo Kα radiation
b = 15.2531 (4) ŵ = 0.16 mm−1
c = 16.0612 (4) ÅT = 153 K
α = 74.639 (2)°0.20 × 0.20 × 0.05 mm
β = 86.561 (2)°
Data collection top
Bruker SMART APEX
diffractometer		10042 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		6419 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.992Rint = 0.034
18419 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.061H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.179Δρmax = 0.66 e Å−3
S = 1.02Δρmin = −0.56 e Å−3
10042 reflectionsAbsolute structure: ?
686 parametersFlack parameter: ?
170 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1o···N8i0.84 (4)1.92 (1)2.755 (5)171 (5)
O1—H1o···N8'i0.84 (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···N10ii0.84 (4)1.91 (1)2.751 (5)178 (5)
O3—H3o···N10'ii0.84 (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)
N2—H2n···O1w0.88 (3)1.88 (1)2.757 (4)175 (4)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+2, −y+1, −z+1.
Acknowledgements top

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

references
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