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In the title compound, C25H23N3O2S, the asymmetric unit consists of two mol­ecules connected by N—H...S hydrogen bonds. The dihedral angles between the phenyl and naphthalimide ring systems in the scorpion-like mol­ecules are 60.63 (7) and 61.09 (8)°. The cyclo­hexane rings adopt chair conformations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015565/sj2253sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015565/sj2253Isup2.hkl
Contains datablock I

CCDC reference: 651413

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.102
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C2 .. 5.04 su
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.06 From the CIF: _reflns_number_total 9357 Count of symmetry unique reflns 5243 Completeness (_total/calc) 178.47% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 4114 Fraction of Friedel pairs measured 0.785 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C38 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C43 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2005); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

1-[(1R,2R)-2-(1,8-Naphthalimido)cyclohexyl]-3-phenylthiourea top
Crystal data top
C25H23N3O2SF(000) = 1808
Mr = 429.52Dx = 1.319 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6606 reflections
a = 14.8211 (7) Åθ = 2.2–25.8°
b = 16.8568 (8) ŵ = 0.18 mm1
c = 17.3150 (8) ÅT = 173 K
V = 4325.9 (4) Å3Block, colorless
Z = 80.41 × 0.30 × 0.27 mm
Data collection top
Bruker AXS SMART 1000 CCD
diffractometer
9357 independent reflections
Radiation source: fine-focus sealed tube6724 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ω scansθmax = 27.1°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1718
Tmin = 0.931, Tmax = 0.954k = 1621
22367 measured reflectionsl = 1522
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.102 w = 1/[σ2(Fo2) + (0.0467P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
9357 reflectionsΔρmax = 0.36 e Å3
559 parametersΔρmin = 0.21 e Å3
0 restraintsAbsolute structure: Flack (1983), 4114 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.04 (6)
Special details top

Experimental. 1H NMR (CDCl3): δ 1.15–2.84 (m, 8H), 4.87–4.93 (m, 1H), 5.20–5.45 (br, 1H), 5.94–5.99 (br, 1H), 6.86–7.26 (m, 5H), 7.41 (br, 1H), 7.72–8.61 (m, 6H); elemental analysis calculated for C25H23N3O2S: C 69.91, H 5.40, N 9.78%; found: C 69.56, H 5.43, N 9.41%.

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
S10.31200 (4)0.41944 (4)0.20893 (4)0.03748 (18)
S20.48536 (4)0.55325 (4)0.35985 (4)0.03692 (17)
C10.0309 (2)0.17532 (19)0.5685 (2)0.0527 (8)
H10.02870.15450.61940.063*
C20.0374 (2)0.12477 (19)0.5073 (2)0.0532 (9)
H20.03940.06920.51610.064*
C30.0413 (2)0.15404 (17)0.43108 (19)0.0475 (8)
H30.04810.11830.38910.057*
C40.03536 (18)0.23417 (16)0.41742 (16)0.0360 (7)
C50.02670 (17)0.28726 (16)0.48001 (15)0.0329 (6)
C60.0274 (2)0.25858 (17)0.55699 (17)0.0431 (7)
C70.0251 (2)0.3142 (2)0.61819 (18)0.0547 (9)
H70.02640.29590.67010.066*
C80.0212 (2)0.3924 (2)0.60407 (17)0.0526 (8)
H80.01990.42860.64610.063*
C90.01914 (19)0.42164 (17)0.52791 (16)0.0424 (7)
H90.01700.47720.51880.051*
C100.02020 (17)0.36965 (14)0.46664 (14)0.0293 (6)
C110.01463 (16)0.39977 (15)0.38687 (14)0.0283 (5)
C120.04325 (18)0.26474 (15)0.33764 (16)0.0345 (6)
C130.01339 (16)0.37899 (14)0.24686 (14)0.0277 (6)
H130.02290.42870.25210.033*
C140.03766 (17)0.32578 (16)0.19007 (15)0.0345 (6)
H14A0.00250.27690.18030.041*
H14B0.09650.31030.21250.041*
C150.05268 (18)0.36971 (17)0.11497 (16)0.0392 (7)
H15A0.09020.41730.12470.047*
H15B0.08570.33500.07850.047*
C160.03633 (18)0.39470 (17)0.07921 (15)0.0397 (7)
H16A0.02490.42480.03110.048*
H16B0.07230.34710.06600.048*
C170.08886 (17)0.44638 (15)0.13598 (14)0.0347 (6)
H17A0.05500.49600.14550.042*
H17B0.14780.46070.11300.042*
C180.10435 (16)0.40354 (14)0.21266 (14)0.0272 (5)
H180.14190.35520.20350.033*
C190.23954 (16)0.47048 (14)0.26561 (14)0.0287 (6)
C200.22223 (16)0.56996 (14)0.37036 (14)0.0278 (5)
C210.14516 (17)0.61267 (14)0.35425 (16)0.0343 (6)
H210.12330.61550.30270.041*
C220.09959 (19)0.65134 (16)0.41279 (18)0.0400 (7)
H220.04560.67940.40150.048*
C230.1316 (2)0.64961 (16)0.48659 (18)0.0420 (7)
H230.09900.67530.52670.050*
C240.2111 (2)0.61059 (16)0.50311 (15)0.0424 (7)
H240.23500.61160.55400.051*
C250.25598 (17)0.56995 (15)0.44520 (14)0.0329 (6)
H250.31000.54200.45670.039*
C260.7786 (2)0.18508 (18)0.58489 (19)0.0521 (8)
H260.78050.13230.60410.062*
C270.7756 (2)0.24672 (18)0.63510 (19)0.0523 (8)
H270.77700.23680.68910.063*
C280.7704 (2)0.32419 (17)0.60817 (17)0.0445 (7)
H280.76560.36670.64400.053*
C290.77208 (17)0.34024 (15)0.52991 (15)0.0328 (6)
C300.77912 (17)0.27765 (15)0.47648 (16)0.0329 (6)
C310.7789 (2)0.19828 (15)0.50398 (17)0.0421 (7)
C320.7772 (2)0.13686 (17)0.4478 (2)0.0560 (9)
H320.77610.08320.46440.067*
C330.7770 (2)0.15317 (17)0.3707 (2)0.0580 (9)
H330.77410.11090.33450.070*
C340.78126 (19)0.23180 (15)0.34428 (17)0.0417 (7)
H340.78320.24270.29050.050*
C350.78254 (16)0.29286 (15)0.39679 (16)0.0320 (6)
C360.78892 (15)0.37592 (14)0.36876 (14)0.0270 (5)
C370.76103 (16)0.42322 (15)0.50192 (15)0.0320 (6)
C380.78617 (16)0.51940 (13)0.39230 (14)0.0267 (5)
H380.81940.51580.34220.032*
C390.84007 (17)0.57597 (14)0.44352 (15)0.0330 (6)
H39A0.80990.58110.49430.040*
H39B0.90120.55400.45230.040*
C400.84773 (18)0.65732 (15)0.40597 (16)0.0372 (7)
H40A0.88020.69370.44120.045*
H40B0.88320.65290.35770.045*
C410.75609 (19)0.69105 (15)0.38791 (19)0.0436 (7)
H41A0.76310.74280.36160.052*
H41B0.72250.70000.43660.052*
C420.70334 (19)0.63542 (14)0.33682 (16)0.0380 (7)
H42A0.73470.63010.28660.046*
H42B0.64290.65830.32690.046*
C430.69250 (16)0.55285 (13)0.37350 (14)0.0276 (5)
H430.65640.55740.42210.033*
C440.55821 (16)0.49828 (14)0.30689 (14)0.0276 (6)
C450.57270 (16)0.39269 (14)0.20638 (15)0.0294 (6)
C460.65337 (17)0.40768 (16)0.16958 (14)0.0347 (6)
H460.67920.45920.17180.042*
C470.6968 (2)0.34783 (18)0.12936 (16)0.0442 (7)
H470.75380.35760.10600.053*
C480.6576 (2)0.2746 (2)0.12341 (18)0.0572 (9)
H480.68770.23330.09640.069*
C490.5750 (3)0.26057 (18)0.1562 (2)0.0590 (9)
H490.54670.21050.14970.071*
C500.5327 (2)0.31921 (15)0.19888 (18)0.0433 (7)
H500.47630.30890.22290.052*
N10.02202 (13)0.34519 (11)0.32624 (11)0.0277 (5)
N20.15104 (13)0.45604 (12)0.26643 (11)0.0298 (5)
H2A0.11840.47990.30200.036*
N30.27109 (13)0.52765 (12)0.31302 (12)0.0326 (5)
H3A0.32840.54010.30780.039*
N40.78047 (12)0.43688 (11)0.42349 (11)0.0259 (4)
N50.64685 (13)0.49915 (11)0.31994 (11)0.0291 (5)
H50.68030.46490.29440.035*
N60.52589 (13)0.45078 (11)0.25087 (12)0.0306 (5)
H60.46820.45630.24030.037*
O10.06687 (14)0.22363 (11)0.28416 (11)0.0484 (5)
O20.00348 (11)0.47027 (9)0.37343 (10)0.0336 (4)
O30.73493 (12)0.47605 (10)0.54328 (11)0.0401 (5)
O40.79965 (12)0.39086 (10)0.30043 (10)0.0331 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0283 (3)0.0518 (4)0.0323 (4)0.0003 (3)0.0003 (3)0.0120 (3)
S20.0306 (3)0.0362 (4)0.0439 (4)0.0067 (3)0.0022 (3)0.0099 (3)
C10.055 (2)0.056 (2)0.047 (2)0.0060 (17)0.0028 (17)0.0194 (17)
C20.0535 (19)0.0407 (18)0.065 (2)0.0034 (15)0.0006 (17)0.0284 (17)
C30.0529 (19)0.0346 (16)0.055 (2)0.0031 (14)0.0026 (16)0.0048 (15)
C40.0361 (16)0.0316 (15)0.0402 (17)0.0003 (12)0.0012 (13)0.0063 (13)
C50.0257 (13)0.0387 (15)0.0344 (15)0.0015 (12)0.0010 (12)0.0037 (12)
C60.0405 (17)0.0496 (18)0.0392 (17)0.0038 (14)0.0001 (14)0.0123 (14)
C70.064 (2)0.073 (2)0.0270 (16)0.0085 (19)0.0004 (16)0.0068 (16)
C80.068 (2)0.059 (2)0.0316 (16)0.0103 (18)0.0014 (16)0.0039 (15)
C90.0483 (17)0.0452 (17)0.0336 (15)0.0052 (14)0.0019 (14)0.0009 (13)
C100.0286 (13)0.0324 (14)0.0267 (13)0.0024 (12)0.0045 (11)0.0012 (11)
C110.0243 (12)0.0305 (14)0.0301 (14)0.0024 (11)0.0015 (11)0.0012 (11)
C120.0351 (15)0.0307 (15)0.0378 (16)0.0001 (12)0.0034 (13)0.0000 (13)
C130.0289 (13)0.0268 (13)0.0274 (13)0.0008 (11)0.0009 (11)0.0001 (11)
C140.0286 (14)0.0407 (16)0.0342 (16)0.0062 (12)0.0004 (12)0.0058 (12)
C150.0332 (15)0.0460 (17)0.0384 (16)0.0022 (13)0.0083 (13)0.0063 (13)
C160.0425 (16)0.0499 (17)0.0266 (14)0.0004 (14)0.0051 (13)0.0032 (13)
C170.0312 (13)0.0426 (15)0.0302 (15)0.0020 (12)0.0009 (12)0.0044 (13)
C180.0278 (12)0.0278 (13)0.0261 (13)0.0021 (10)0.0010 (11)0.0056 (11)
C190.0306 (14)0.0300 (13)0.0254 (14)0.0009 (11)0.0019 (11)0.0027 (11)
C200.0305 (13)0.0265 (13)0.0262 (13)0.0049 (11)0.0017 (11)0.0014 (11)
C210.0363 (14)0.0309 (14)0.0357 (16)0.0002 (12)0.0039 (13)0.0013 (12)
C220.0371 (16)0.0313 (15)0.052 (2)0.0043 (13)0.0024 (14)0.0012 (14)
C230.0472 (18)0.0367 (16)0.0423 (18)0.0047 (14)0.0121 (15)0.0042 (13)
C240.0573 (18)0.0440 (17)0.0260 (14)0.0046 (15)0.0004 (14)0.0003 (13)
C250.0340 (14)0.0340 (15)0.0307 (14)0.0053 (12)0.0011 (12)0.0044 (12)
C260.062 (2)0.0412 (18)0.053 (2)0.0024 (16)0.0096 (17)0.0220 (16)
C270.064 (2)0.055 (2)0.0379 (17)0.0007 (17)0.0048 (16)0.0150 (16)
C280.0533 (18)0.0480 (18)0.0322 (16)0.0014 (15)0.0037 (14)0.0033 (13)
C290.0323 (14)0.0347 (14)0.0315 (15)0.0001 (12)0.0014 (12)0.0036 (12)
C300.0277 (14)0.0332 (14)0.0379 (16)0.0045 (11)0.0038 (12)0.0040 (12)
C310.0487 (17)0.0320 (16)0.0456 (18)0.0029 (14)0.0062 (15)0.0090 (14)
C320.070 (2)0.0265 (15)0.071 (2)0.0048 (15)0.0180 (19)0.0085 (16)
C330.082 (2)0.0300 (16)0.062 (2)0.0026 (16)0.013 (2)0.0067 (16)
C340.0497 (17)0.0330 (15)0.0425 (17)0.0003 (13)0.0104 (15)0.0033 (13)
C350.0297 (14)0.0286 (14)0.0378 (16)0.0034 (12)0.0016 (12)0.0025 (12)
C360.0216 (12)0.0291 (13)0.0302 (15)0.0017 (10)0.0011 (11)0.0001 (11)
C370.0295 (13)0.0363 (15)0.0301 (14)0.0035 (12)0.0016 (11)0.0015 (12)
C380.0295 (13)0.0238 (13)0.0268 (13)0.0003 (11)0.0027 (11)0.0015 (10)
C390.0309 (14)0.0321 (15)0.0360 (15)0.0013 (12)0.0043 (12)0.0052 (12)
C400.0384 (15)0.0303 (15)0.0428 (17)0.0087 (13)0.0028 (13)0.0069 (12)
C410.0498 (18)0.0256 (14)0.0555 (19)0.0036 (13)0.0011 (15)0.0011 (13)
C420.0386 (15)0.0307 (14)0.0447 (17)0.0019 (12)0.0088 (14)0.0034 (12)
C430.0284 (12)0.0256 (12)0.0288 (14)0.0007 (11)0.0004 (11)0.0024 (11)
C440.0325 (14)0.0243 (13)0.0261 (13)0.0006 (11)0.0024 (11)0.0059 (11)
C450.0359 (14)0.0284 (14)0.0240 (13)0.0035 (11)0.0039 (12)0.0020 (11)
C460.0336 (14)0.0419 (16)0.0286 (14)0.0042 (13)0.0021 (12)0.0015 (12)
C470.0405 (16)0.061 (2)0.0306 (16)0.0128 (15)0.0001 (14)0.0023 (14)
C480.079 (3)0.049 (2)0.043 (2)0.0239 (19)0.0050 (18)0.0048 (15)
C490.086 (3)0.0311 (16)0.060 (2)0.0005 (16)0.017 (2)0.0039 (16)
C500.0521 (18)0.0319 (16)0.0460 (18)0.0049 (14)0.0073 (15)0.0006 (13)
N10.0290 (11)0.0277 (11)0.0263 (11)0.0013 (9)0.0031 (9)0.0019 (9)
N20.0275 (11)0.0356 (12)0.0262 (12)0.0030 (10)0.0018 (9)0.0070 (9)
N30.0265 (11)0.0415 (13)0.0297 (12)0.0055 (10)0.0017 (9)0.0084 (10)
N40.0270 (10)0.0258 (11)0.0249 (11)0.0005 (9)0.0003 (9)0.0004 (9)
N50.0266 (11)0.0287 (11)0.0320 (12)0.0048 (9)0.0009 (10)0.0042 (9)
N60.0264 (11)0.0317 (11)0.0339 (12)0.0040 (10)0.0035 (10)0.0033 (10)
O10.0701 (14)0.0370 (11)0.0382 (12)0.0123 (10)0.0025 (11)0.0075 (10)
O20.0414 (10)0.0264 (9)0.0331 (10)0.0029 (8)0.0042 (8)0.0015 (8)
O30.0524 (12)0.0369 (10)0.0309 (10)0.0004 (9)0.0102 (9)0.0062 (9)
O40.0413 (10)0.0312 (9)0.0267 (10)0.0031 (8)0.0010 (9)0.0014 (8)
Geometric parameters (Å, º) top
S1—C191.690 (3)C26—C311.418 (4)
S2—C441.693 (2)C26—H260.9500
C1—C21.363 (5)C27—C281.389 (4)
C1—C61.418 (4)C27—H270.9500
C1—H10.9500C28—C291.382 (4)
C2—C31.410 (4)C28—H280.9500
C2—H20.9500C29—C301.407 (4)
C3—C41.374 (4)C29—C371.489 (3)
C3—H30.9500C30—C351.404 (4)
C4—C51.411 (4)C30—C311.420 (3)
C4—C121.479 (4)C31—C321.420 (4)
C5—C101.411 (3)C32—C331.363 (4)
C5—C61.418 (4)C32—H320.9500
C6—C71.415 (4)C33—C341.404 (4)
C7—C81.342 (4)C33—H330.9500
C7—H70.9500C34—C351.373 (4)
C8—C91.408 (4)C34—H340.9500
C8—H80.9500C35—C361.485 (3)
C9—C101.376 (4)C36—O41.220 (3)
C9—H90.9500C36—N41.404 (3)
C10—C111.474 (3)C37—O31.207 (3)
C11—O21.222 (3)C37—N41.407 (3)
C11—N11.400 (3)C38—N41.495 (3)
C12—O11.208 (3)C38—C391.528 (3)
C12—N11.406 (3)C38—C431.533 (3)
C13—N11.493 (3)C38—H381.0000
C13—C181.529 (3)C39—C401.522 (4)
C13—C141.531 (3)C39—H39A0.9900
C13—H131.0000C39—H39B0.9900
C14—C151.513 (4)C40—C411.505 (4)
C14—H14A0.9900C40—H40A0.9900
C14—H14B0.9900C40—H40B0.9900
C15—C161.517 (4)C41—C421.508 (4)
C15—H15A0.9900C41—H41A0.9900
C15—H15B0.9900C41—H41B0.9900
C16—C171.527 (4)C42—C431.538 (3)
C16—H16A0.9900C42—H42A0.9900
C16—H16B0.9900C42—H42B0.9900
C17—C181.529 (3)C43—N51.462 (3)
C17—H17A0.9900C43—H431.0000
C17—H17B0.9900C44—N51.333 (3)
C18—N21.459 (3)C44—N61.346 (3)
C18—H181.0000C45—C461.378 (3)
C19—N21.334 (3)C45—C501.379 (3)
C19—N31.350 (3)C45—N61.426 (3)
C20—C211.379 (3)C46—C471.385 (4)
C20—C251.389 (3)C46—H460.9500
C20—N31.421 (3)C47—C481.369 (4)
C21—C221.381 (4)C47—H470.9500
C21—H210.9500C48—C491.370 (5)
C22—C231.363 (4)C48—H480.9500
C22—H220.9500C49—C501.384 (4)
C23—C241.380 (4)C49—H490.9500
C23—H230.9500C50—H500.9500
C24—C251.385 (4)N2—H2A0.8800
C24—H240.9500N3—H3A0.8800
C25—H250.9500N5—H50.8800
C26—C271.356 (4)N6—H60.8800
C2—C1—C6120.8 (3)C28—C29—C30120.0 (2)
C2—C1—H1119.6C28—C29—C37120.1 (2)
C6—C1—H1119.6C30—C29—C37119.9 (2)
C1—C2—C3120.8 (3)C35—C30—C29120.8 (2)
C1—C2—H2119.6C35—C30—C31120.1 (2)
C3—C2—H2119.6C29—C30—C31119.1 (2)
C4—C3—C2120.2 (3)C26—C31—C32124.2 (3)
C4—C3—H3119.9C26—C31—C30118.6 (3)
C2—C3—H3119.9C32—C31—C30117.2 (3)
C3—C4—C5119.8 (3)C33—C32—C31121.6 (3)
C3—C4—C12119.9 (3)C33—C32—H32119.2
C5—C4—C12120.2 (2)C31—C32—H32119.2
C10—C5—C4120.3 (2)C32—C33—C34120.7 (3)
C10—C5—C6119.4 (3)C32—C33—H33119.7
C4—C5—C6120.3 (2)C34—C33—H33119.7
C7—C6—C5118.5 (3)C35—C34—C33119.5 (3)
C7—C6—C1123.4 (3)C35—C34—H34120.3
C5—C6—C1118.0 (3)C33—C34—H34120.3
C8—C7—C6121.0 (3)C34—C35—C30120.9 (2)
C8—C7—H7119.5C34—C35—C36119.4 (2)
C6—C7—H7119.5C30—C35—C36119.7 (2)
C7—C8—C9121.0 (3)O4—C36—N4121.0 (2)
C7—C8—H8119.5O4—C36—C35121.3 (2)
C9—C8—H8119.5N4—C36—C35117.6 (2)
C10—C9—C8119.9 (3)O3—C37—N4121.2 (2)
C10—C9—H9120.0O3—C37—C29122.4 (2)
C8—C9—H9120.0N4—C37—C29116.4 (2)
C9—C10—C5120.1 (2)N4—C38—C39113.6 (2)
C9—C10—C11120.2 (2)N4—C38—C43111.58 (18)
C5—C10—C11119.8 (2)C39—C38—C43111.54 (19)
O2—C11—N1120.5 (2)N4—C38—H38106.5
O2—C11—C10121.4 (2)C39—C38—H38106.5
N1—C11—C10118.2 (2)C43—C38—H38106.5
O1—C12—N1120.7 (2)C40—C39—C38110.7 (2)
O1—C12—C4122.6 (2)C40—C39—H39A109.5
N1—C12—C4116.7 (2)C38—C39—H39A109.5
N1—C13—C18112.6 (2)C40—C39—H39B109.5
N1—C13—C14114.20 (19)C38—C39—H39B109.5
C18—C13—C14110.2 (2)H39A—C39—H39B108.1
N1—C13—H13106.4C41—C40—C39111.2 (2)
C18—C13—H13106.4C41—C40—H40A109.4
C14—C13—H13106.4C39—C40—H40A109.4
C15—C14—C13109.8 (2)C41—C40—H40B109.4
C15—C14—H14A109.7C39—C40—H40B109.4
C13—C14—H14A109.7H40A—C40—H40B108.0
C15—C14—H14B109.7C40—C41—C42110.8 (2)
C13—C14—H14B109.7C40—C41—H41A109.5
H14A—C14—H14B108.2C42—C41—H41A109.5
C14—C15—C16111.0 (2)C40—C41—H41B109.5
C14—C15—H15A109.4C42—C41—H41B109.5
C16—C15—H15A109.4H41A—C41—H41B108.1
C14—C15—H15B109.4C41—C42—C43112.0 (2)
C16—C15—H15B109.4C41—C42—H42A109.2
H15A—C15—H15B108.0C43—C42—H42A109.2
C15—C16—C17109.8 (2)C41—C42—H42B109.2
C15—C16—H16A109.7C43—C42—H42B109.2
C17—C16—H16A109.7H42A—C42—H42B107.9
C15—C16—H16B109.7N5—C43—C38109.03 (18)
C17—C16—H16B109.7N5—C43—C42110.28 (19)
H16A—C16—H16B108.2C38—C43—C42109.02 (19)
C16—C17—C18111.5 (2)N5—C43—H43109.5
C16—C17—H17A109.3C38—C43—H43109.5
C18—C17—H17A109.3C42—C43—H43109.5
C16—C17—H17B109.3N5—C44—N6118.6 (2)
C18—C17—H17B109.3N5—C44—S2122.06 (19)
H17A—C17—H17B108.0N6—C44—S2119.28 (18)
N2—C18—C17109.81 (19)C46—C45—C50119.6 (2)
N2—C18—C13109.58 (19)C46—C45—N6123.1 (2)
C17—C18—C13109.4 (2)C50—C45—N6117.3 (2)
N2—C18—H18109.4C45—C46—C47120.2 (3)
C17—C18—H18109.4C45—C46—H46119.9
C13—C18—H18109.4C47—C46—H46119.9
N2—C19—N3117.7 (2)C48—C47—C46119.8 (3)
N2—C19—S1122.55 (19)C48—C47—H47120.1
N3—C19—S1119.77 (18)C46—C47—H47120.1
C21—C20—C25119.2 (2)C47—C48—C49120.3 (3)
C21—C20—N3122.9 (2)C47—C48—H48119.9
C25—C20—N3117.9 (2)C49—C48—H48119.9
C20—C21—C22120.2 (3)C48—C49—C50120.2 (3)
C20—C21—H21119.9C48—C49—H49119.9
C22—C21—H21119.9C50—C49—H49119.9
C23—C22—C21120.5 (3)C45—C50—C49119.8 (3)
C23—C22—H22119.7C45—C50—H50120.1
C21—C22—H22119.7C49—C50—H50120.1
C22—C23—C24120.1 (3)C11—N1—C12123.1 (2)
C22—C23—H23119.9C11—N1—C13115.64 (19)
C24—C23—H23119.9C12—N1—C13121.1 (2)
C23—C24—C25119.7 (3)C19—N2—C18124.8 (2)
C23—C24—H24120.1C19—N2—H2A117.6
C25—C24—H24120.1C18—N2—H2A117.6
C24—C25—C20120.2 (2)C19—N3—C20127.4 (2)
C24—C25—H25119.9C19—N3—H3A116.3
C20—C25—H25119.9C20—N3—H3A116.3
C27—C26—C31120.9 (3)C36—N4—C37123.4 (2)
C27—C26—H26119.6C36—N4—C38115.62 (19)
C31—C26—H26119.6C37—N4—C38120.84 (19)
C26—C27—C28120.5 (3)C44—N5—C43124.8 (2)
C26—C27—H27119.8C44—N5—H5117.6
C28—C27—H27119.8C43—N5—H5117.6
C29—C28—C27120.8 (3)C44—N6—C45128.7 (2)
C29—C28—H28119.6C44—N6—H6115.7
C27—C28—H28119.6C45—N6—H6115.7
C6—C1—C2—C30.3 (5)C29—C30—C35—C34174.1 (2)
C1—C2—C3—C42.3 (5)C31—C30—C35—C343.2 (4)
C2—C3—C4—C51.0 (4)C29—C30—C35—C366.7 (4)
C2—C3—C4—C12177.5 (3)C31—C30—C35—C36175.9 (2)
C3—C4—C5—C10179.8 (3)C34—C35—C36—O45.4 (4)
C12—C4—C5—C103.7 (4)C30—C35—C36—O4173.8 (2)
C3—C4—C5—C62.3 (4)C34—C35—C36—N4173.4 (2)
C12—C4—C5—C6174.2 (2)C30—C35—C36—N47.4 (3)
C10—C5—C6—C72.5 (4)C28—C29—C37—O313.3 (4)
C4—C5—C6—C7175.5 (3)C30—C29—C37—O3163.1 (2)
C10—C5—C6—C1177.9 (3)C28—C29—C37—N4168.3 (2)
C4—C5—C6—C14.1 (4)C30—C29—C37—N415.3 (3)
C2—C1—C6—C7176.7 (3)N4—C38—C39—C40176.6 (2)
C2—C1—C6—C52.8 (5)C43—C38—C39—C4056.2 (3)
C5—C6—C7—C80.9 (5)C38—C39—C40—C4156.3 (3)
C1—C6—C7—C8179.6 (3)C39—C40—C41—C4256.8 (3)
C6—C7—C8—C90.1 (5)C40—C41—C42—C4357.5 (3)
C7—C8—C9—C100.6 (5)N4—C38—C43—N555.9 (2)
C8—C9—C10—C52.3 (4)C39—C38—C43—N5175.85 (19)
C8—C9—C10—C11177.8 (3)N4—C38—C43—C42176.33 (19)
C4—C5—C10—C9174.7 (3)C39—C38—C43—C4255.4 (3)
C6—C5—C10—C93.3 (4)C41—C42—C43—N5175.9 (2)
C4—C5—C10—C115.2 (4)C41—C42—C43—C3856.2 (3)
C6—C5—C10—C11176.8 (2)C50—C45—C46—C474.0 (4)
C9—C10—C11—O24.5 (4)N6—C45—C46—C47177.9 (2)
C5—C10—C11—O2175.5 (2)C45—C46—C47—C482.8 (4)
C9—C10—C11—N1175.8 (2)C46—C47—C48—C490.8 (5)
C5—C10—C11—N14.1 (3)C47—C48—C49—C503.2 (5)
C3—C4—C12—O110.2 (4)C46—C45—C50—C491.7 (4)
C5—C4—C12—O1166.3 (3)N6—C45—C50—C49179.9 (3)
C3—C4—C12—N1170.0 (2)C48—C49—C50—C451.9 (5)
C5—C4—C12—N113.5 (4)O2—C11—N1—C12173.9 (2)
N1—C13—C14—C15172.9 (2)C10—C11—N1—C126.5 (3)
C18—C13—C14—C1559.2 (3)O2—C11—N1—C131.2 (3)
C13—C14—C15—C1659.1 (3)C10—C11—N1—C13178.4 (2)
C14—C15—C16—C1757.6 (3)O1—C12—N1—C11164.8 (2)
C15—C16—C17—C1856.8 (3)C4—C12—N1—C1115.0 (3)
C16—C17—C18—N2177.4 (2)O1—C12—N1—C1310.0 (4)
C16—C17—C18—C1357.2 (3)C4—C12—N1—C13170.1 (2)
N1—C13—C18—N252.9 (3)C18—C13—N1—C1191.0 (2)
C14—C13—C18—N2178.37 (19)C14—C13—N1—C11142.3 (2)
N1—C13—C18—C17173.28 (19)C18—C13—N1—C1284.2 (3)
C14—C13—C18—C1757.9 (3)C14—C13—N1—C1242.5 (3)
C25—C20—C21—C223.5 (4)N3—C19—N2—C18172.2 (2)
N3—C20—C21—C22178.7 (2)S1—C19—N2—C188.6 (3)
C20—C21—C22—C231.9 (4)C17—C18—N2—C1979.5 (3)
C21—C22—C23—C241.5 (4)C13—C18—N2—C19160.4 (2)
C22—C23—C24—C253.1 (4)N2—C19—N3—C206.8 (4)
C23—C24—C25—C201.5 (4)S1—C19—N3—C20172.36 (19)
C21—C20—C25—C241.8 (4)C21—C20—N3—C1956.7 (3)
N3—C20—C25—C24179.7 (2)C25—C20—N3—C19125.5 (3)
C31—C26—C27—C281.6 (5)O4—C36—N4—C37174.9 (2)
C26—C27—C28—C292.8 (5)C35—C36—N4—C373.9 (3)
C27—C28—C29—C300.0 (4)O4—C36—N4—C380.4 (3)
C27—C28—C29—C37176.4 (3)C35—C36—N4—C38179.24 (19)
C28—C29—C30—C35178.9 (3)O3—C37—N4—C36163.5 (2)
C37—C29—C30—C354.7 (4)C29—C37—N4—C3614.9 (3)
C28—C29—C30—C313.8 (4)O3—C37—N4—C3811.5 (3)
C37—C29—C30—C31172.6 (2)C29—C37—N4—C38170.0 (2)
C27—C26—C31—C32176.5 (3)C39—C38—N4—C36139.6 (2)
C27—C26—C31—C302.1 (5)C43—C38—N4—C3693.3 (2)
C35—C30—C31—C26177.8 (3)C39—C38—N4—C3745.0 (3)
C29—C30—C31—C264.8 (4)C43—C38—N4—C3782.2 (3)
C35—C30—C31—C323.4 (4)N6—C44—N5—C43174.0 (2)
C29—C30—C31—C32174.0 (3)S2—C44—N5—C437.5 (3)
C26—C31—C32—C33179.6 (3)C38—C43—N5—C44161.9 (2)
C30—C31—C32—C330.9 (5)C42—C43—N5—C4478.4 (3)
C31—C32—C33—C341.9 (5)N5—C44—N6—C457.2 (4)
C32—C33—C34—C352.2 (5)S2—C44—N6—C45171.33 (19)
C33—C34—C35—C300.4 (4)C46—C45—N6—C4449.4 (4)
C33—C34—C35—C36178.7 (3)C50—C45—N6—C44132.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O20.882.112.876 (3)145
N3—H3A···S20.882.503.306 (2)152
N5—H5···O40.882.172.928 (3)145
N6—H6···S10.882.463.295 (2)159
 

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