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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o535.
Published online 2008 January 30. doi:  10.1107/S1600536808002845
PMCID: PMC2960238

2-(Dibutyl­amino)-3-(4-fluoro­phen­yl)-5,6,7,8-tetra­hydro-7-methyl-6,8-di­phenyl­pyridine­[3′,4′:2,3]thieno[5,4-d]pyrimidin-4(3H)-one

Abstract

In the crystal structure of the title compound, C36H39FN4OS, the two fused rings of the thienopyrimidine system are coplanar. The 4-fluoro­phenyl ring is twisted with respect to the heterocyclic pyrimidinone ring by 67.21 (14)°. The piperidine ring shows a half-chair conformation. One of the n-butyl chains is disordered equally over two sites. The crystal packing is stabilized by C—H(...)O hydrogen bonds.

Related literature

The preparation and biological activity are described by Walter (1999a [triangle],b [triangle]). For related literature, see: Ding et al. (2004 [triangle]). For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2006 [triangle], 2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o535-scheme1.jpg

Experimental

Crystal data

  • C36H39FN4OS
  • M r = 594.77
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o535-efi1.jpg
  • a = 13.723 (4) Å
  • b = 9.836 (3) Å
  • c = 24.5496 (15) Å
  • β = 101.342 (2)°
  • V = 3249.0 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.14 mm−1
  • T = 294 (2) K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.973, T max = 0.986
  • 32225 measured reflections
  • 6359 independent reflections
  • 4457 reflections with I > 2σ(I)
  • R int = 0.049

Refinement

  • R[F 2 > 2σ(F 2)] = 0.075
  • wR(F 2) = 0.178
  • S = 1.10
  • 6359 reflections
  • 420 parameters
  • H-atom parameters constrained
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002845/bt2671sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002845/bt2671Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge financial support of this work by the Key Science Research Project of Hubei Provincial Department of Education (grant No. D200724001) and the Science Research Project of Yunyang Medical College (grant No. 2006QDJ16).

supplementary crystallographic information

Comment

The derivatives of heterocycles containing the thienopyrimidine system, which are well known bioisosteres of quinazolines, are of great importance because of their remarkable biological properties (Walter, 1999a; Walter, 1999b; Ding et al., 2004). Recently, we have focused on the synthesis of the fused heterocycle systems containing thienopyrimidine via aza-Wittig reaction at room temperature. Some X-ray crystal structures of fused pyrimidinone derivatives have been reported (Hu et al., 2006; 2007). The title compound (Fig. 1) may be used as a precursor for obtaining bioactive molecules. The two fused rings of the thienopyrimidine ring system are coplanar, making a dihedral angle of 0.36 (13)°. The p-fluorophenyl ring is twisted with respect to pyrimidinone ring by 67.21 (14)°. The piperidine ring shows a half-chair conformation [[var phi] =25.9 (4)° and θ = 49.9 (3)°, puckering Amplitude = 0.515 (3) Å]. One of the n-butyl chains is disordered over two sites. The crystal packing is stabilized by C—H···O hydrogen bonds interactions (Table 1).

Experimental

To a solution of ethyl 2-((p-flurophenylimino)methyleneamino)-4,5,6,7-tetrahydro-6-methyl- 5,7-diphenylthieno[2,3-c]pyridine-3-carboxylate (3 mmol) in dichloromethane (5 ml) was added dibutylamine (3 mmol). After stirring the reaction mixture for 1 h, the solvent was removed and anhydrous ethanol (10 ml) with several drops of EtONa in EtOH was added. The mixture was stirred for 4 h at room temperature. The solution was concentrated under reduced pressure and the residue was recrystallized from dichloromethane and ethanol (v/v = 1:1) to give the title compound in a yield of 80%. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:3 v/v) at room temperature.

Refinement

All H-atoms were positioned with idealized geometry and refined using a riding model with Uiso(H)= 1.5Ueq(C) for methyl H atoms and Uiso(H) =1.2Ueq(C) for all other H atoms and with C—H ranging from 0.93° to 0.98 Å. The methyl groups were allowed to rotate but not to tip. Three atoms of one n-butyl chains are disordered over two sites with site occupation factors of 0.540 (12) and 0.460 (12).

Figures

Fig. 1.
Molecular structure of the title compound with labelling and displacement ellipsoids drawn at the 50% probability level

Crystal data

C36H39FN4OSF000 = 1264
Mr = 594.77Dx = 1.216 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4792 reflections
a = 13.723 (4) Åθ = 2.2–21.1º
b = 9.836 (3) ŵ = 0.14 mm1
c = 24.5496 (15) ÅT = 294 (2) K
β = 101.342 (2)ºBlock, colorless
V = 3249.0 (14) Å30.20 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART 4K CCD area-detector diffractometer6359 independent reflections
Radiation source: fine-focus sealed tube4457 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.049
T = 294(2) Kθmax = 26.0º
[var phi] and ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Bruker, 2001)h = −16→16
Tmin = 0.973, Tmax = 0.986k = −12→12
32225 measured reflectionsl = −29→30

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.075H-atom parameters constrained
wR(F2) = 0.178  w = 1/[σ2(Fo2) + (0.0743P)2 + 1.2986P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
6359 reflectionsΔρmax = 0.40 e Å3
420 parametersΔρmin = −0.18 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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)

xyzUiso*/UeqOcc. (<1)
C10.3447 (2)0.2687 (3)0.22128 (13)0.0579 (8)
C20.3770 (3)0.3694 (5)0.19044 (17)0.0870 (12)
H20.34660.45430.18770.104*
C30.4545 (4)0.3456 (7)0.1635 (2)0.1172 (18)
H30.47590.41520.14310.141*
C40.4996 (4)0.2237 (9)0.1661 (3)0.136 (3)
H40.55110.20840.14720.163*
C50.4692 (4)0.1243 (7)0.1963 (3)0.131 (2)
H50.50010.03990.19820.158*
C60.3933 (3)0.1448 (4)0.22453 (19)0.0905 (13)
H60.37450.07500.24590.109*
C70.2588 (2)0.2901 (3)0.25038 (12)0.0510 (7)
H70.24450.20340.26680.061*
C80.2858 (2)0.3941 (3)0.29718 (11)0.0510 (7)
H8A0.33550.35550.32670.061*
H8B0.31430.47390.28320.061*
C90.19730 (18)0.4348 (3)0.31993 (10)0.0411 (6)
C100.10476 (18)0.4041 (3)0.29181 (11)0.0427 (6)
C110.1498 (2)0.2452 (4)0.16164 (14)0.0767 (11)
H11A0.15240.15190.17330.115*
H11B0.19980.26120.14000.115*
H11C0.08540.26450.13960.115*
C120.08097 (19)0.3292 (3)0.23755 (11)0.0474 (7)
H120.06690.23410.24500.057*
C13−0.0112 (2)0.3913 (3)0.20114 (11)0.0503 (7)
C14−0.1018 (2)0.3286 (4)0.19700 (14)0.0644 (9)
H14−0.10590.24530.21430.077*
C15−0.1881 (3)0.3895 (5)0.16690 (18)0.0912 (13)
H15−0.24940.34720.16430.109*
C16−0.1813 (3)0.5119 (5)0.14142 (17)0.0936 (14)
H16−0.23830.55330.12170.112*
C17−0.0902 (3)0.5741 (4)0.14485 (14)0.0851 (12)
H17−0.08600.65670.12700.102*
C18−0.0060 (3)0.5145 (4)0.17451 (13)0.0715 (10)
H180.05520.55710.17680.086*
C190.19517 (18)0.5079 (3)0.37045 (10)0.0398 (6)
C200.10039 (18)0.5317 (3)0.37838 (10)0.0421 (6)
C210.27613 (19)0.5607 (3)0.41048 (11)0.0416 (6)
C220.14679 (18)0.6441 (3)0.45949 (11)0.0438 (7)
C230.32616 (19)0.6976 (3)0.49318 (11)0.0434 (6)
C240.3317 (2)0.8363 (3)0.49281 (12)0.0539 (8)
H240.28260.88650.46990.065*
C250.4101 (2)0.9018 (4)0.52640 (15)0.0714 (10)
H250.41400.99620.52710.086*
C260.4817 (2)0.8244 (4)0.55861 (15)0.0740 (10)
C270.4788 (2)0.6871 (4)0.55940 (14)0.0716 (10)
H270.52890.63760.58190.086*
C280.3998 (2)0.6217 (3)0.52609 (12)0.0581 (8)
H280.39620.52730.52580.070*
C290.0333 (2)0.7957 (3)0.49500 (14)0.0594 (8)
H29A0.04260.87200.52050.071*
H29B0.02230.83280.45770.071*
C30−0.0583 (2)0.7227 (4)0.50169 (15)0.0665 (9)
H30A−0.04840.68410.53870.080*
H30B−0.07040.64840.47520.080*
C31−0.1489 (2)0.8153 (4)0.49285 (15)0.0700 (10)
H31A−0.13690.88820.51990.084*
H31B−0.15710.85590.45620.084*
C32−0.2429 (3)0.7447 (5)0.4977 (2)0.1140 (17)
H32A−0.25720.67500.46990.171*
H32B−0.29650.80920.49250.171*
H32C−0.23570.70430.53390.171*
C330.1645 (2)0.6617 (4)0.56025 (12)0.0669 (9)
H33A0.10870.61530.57090.080*0.540 (12)
H33B0.21260.59200.55630.080*0.540 (12)
H33C0.22430.60840.56140.080*0.460 (12)
H33D0.11460.60480.57190.080*0.460 (12)
C340.2095 (12)0.7431 (12)0.6075 (4)0.066 (3)0.540 (12)
H34A0.15960.80480.61630.079*0.540 (12)
H34B0.26160.79800.59710.079*0.540 (12)
C350.2531 (8)0.6640 (10)0.6590 (3)0.068 (3)0.540 (12)
H35A0.20140.61010.67040.082*0.540 (12)
H35B0.30350.60230.65090.082*0.540 (12)
C360.2984 (9)0.7568 (10)0.7053 (4)0.104 (4)0.540 (12)
H36A0.35320.80460.69520.156*0.540 (12)
H36B0.32160.70440.73830.156*0.540 (12)
H36C0.24940.82100.71210.156*0.540 (12)
C35'0.2274 (7)0.7482 (16)0.6599 (3)0.084 (4)0.460 (12)
H35C0.21910.82360.68400.101*0.460 (12)
H35D0.18830.67270.66920.101*0.460 (12)
C36'0.3346 (8)0.7077 (14)0.6708 (7)0.118 (5)0.460 (12)
H36D0.34230.62630.65050.177*0.460 (12)
H36E0.35700.69140.70980.177*0.460 (12)
H36F0.37330.77940.65910.177*0.460 (12)
C34'0.1879 (13)0.7894 (15)0.6001 (5)0.073 (4)0.460 (12)
H34C0.23650.84650.58730.088*0.460 (12)
H34D0.12770.84240.59820.088*0.460 (12)
F10.56013 (15)0.8889 (3)0.59104 (11)0.1141 (9)
N10.16778 (16)0.3340 (3)0.21066 (9)0.0490 (6)
N20.07372 (15)0.5982 (2)0.42205 (9)0.0460 (6)
N30.24634 (15)0.6284 (2)0.45583 (9)0.0425 (5)
N40.12771 (17)0.7164 (3)0.50414 (9)0.0543 (6)
O10.36369 (14)0.5545 (2)0.40787 (8)0.0573 (6)
S10.01216 (5)0.46324 (8)0.32512 (3)0.0508 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0445 (16)0.074 (2)0.0542 (19)0.0018 (15)0.0070 (14)−0.0218 (17)
C20.079 (3)0.107 (3)0.085 (3)−0.001 (2)0.041 (2)0.002 (2)
C30.087 (3)0.182 (6)0.097 (3)−0.014 (4)0.054 (3)−0.018 (4)
C40.056 (3)0.235 (8)0.125 (5)−0.007 (4)0.039 (3)−0.087 (5)
C50.061 (3)0.156 (6)0.174 (6)0.032 (3)0.016 (3)−0.081 (5)
C60.067 (2)0.089 (3)0.112 (3)0.014 (2)0.008 (2)−0.025 (2)
C70.0510 (16)0.0564 (18)0.0459 (17)0.0009 (14)0.0106 (13)−0.0015 (14)
C80.0448 (15)0.068 (2)0.0388 (15)0.0030 (14)0.0046 (12)−0.0073 (14)
C90.0400 (14)0.0488 (16)0.0347 (14)−0.0002 (12)0.0081 (11)0.0020 (12)
C100.0399 (14)0.0525 (17)0.0355 (14)−0.0058 (12)0.0066 (11)−0.0016 (12)
C110.058 (2)0.119 (3)0.055 (2)−0.014 (2)0.0159 (16)−0.035 (2)
C120.0450 (15)0.0556 (18)0.0411 (16)−0.0080 (13)0.0071 (12)−0.0064 (13)
C130.0488 (16)0.067 (2)0.0336 (15)−0.0044 (14)0.0038 (12)−0.0170 (14)
C140.0482 (18)0.077 (2)0.066 (2)−0.0068 (16)0.0060 (15)−0.0212 (18)
C150.053 (2)0.120 (4)0.094 (3)−0.001 (2)−0.002 (2)−0.039 (3)
C160.084 (3)0.113 (4)0.068 (3)0.033 (3)−0.023 (2)−0.029 (3)
C170.102 (3)0.091 (3)0.051 (2)0.012 (2)−0.012 (2)−0.0048 (19)
C180.080 (2)0.080 (3)0.0490 (19)−0.0041 (19)−0.0023 (17)0.0017 (18)
C190.0375 (14)0.0448 (15)0.0364 (14)−0.0001 (11)0.0058 (11)0.0009 (12)
C200.0377 (14)0.0516 (17)0.0358 (14)0.0007 (12)0.0042 (11)0.0012 (12)
C210.0390 (15)0.0494 (17)0.0355 (14)0.0040 (12)0.0051 (11)0.0017 (12)
C220.0379 (14)0.0559 (17)0.0366 (15)0.0056 (12)0.0051 (11)−0.0015 (13)
C230.0402 (14)0.0524 (18)0.0357 (14)0.0009 (12)0.0029 (11)−0.0049 (12)
C240.0487 (16)0.059 (2)0.0503 (17)0.0029 (14)0.0008 (13)0.0050 (15)
C250.064 (2)0.061 (2)0.085 (3)−0.0114 (17)0.0048 (18)−0.0115 (19)
C260.0468 (18)0.093 (3)0.075 (2)−0.0105 (18)−0.0055 (16)−0.026 (2)
C270.0550 (19)0.083 (3)0.065 (2)0.0176 (17)−0.0177 (16)−0.0154 (19)
C280.0512 (17)0.0601 (19)0.0563 (19)0.0085 (15)−0.0060 (14)−0.0049 (15)
C290.0628 (19)0.058 (2)0.0566 (19)0.0073 (16)0.0109 (15)−0.0101 (16)
C300.062 (2)0.069 (2)0.071 (2)0.0080 (17)0.0174 (17)−0.0034 (18)
C310.061 (2)0.080 (2)0.068 (2)0.0180 (18)0.0116 (17)0.0058 (19)
C320.068 (3)0.108 (4)0.170 (5)0.010 (2)0.032 (3)0.019 (3)
C330.0541 (18)0.104 (3)0.0436 (18)0.0043 (18)0.0125 (14)−0.0012 (18)
C340.075 (8)0.078 (6)0.038 (5)0.001 (5)−0.003 (4)0.002 (4)
C350.071 (6)0.074 (6)0.057 (4)−0.016 (4)0.006 (4)−0.001 (4)
C360.123 (8)0.112 (8)0.068 (6)−0.016 (6)−0.004 (5)−0.002 (5)
C35'0.084 (7)0.113 (11)0.053 (6)−0.016 (7)0.005 (5)−0.010 (6)
C36'0.113 (10)0.119 (10)0.115 (12)0.018 (8)0.005 (8)0.003 (8)
C34'0.060 (7)0.113 (11)0.042 (6)0.007 (7)−0.003 (4)−0.001 (7)
F10.0640 (13)0.128 (2)0.132 (2)−0.0187 (13)−0.0241 (13)−0.0511 (17)
N10.0426 (13)0.0682 (16)0.0365 (12)−0.0072 (11)0.0083 (10)−0.0095 (11)
N20.0389 (12)0.0603 (15)0.0380 (13)0.0010 (11)0.0055 (10)−0.0082 (11)
N30.0376 (12)0.0517 (14)0.0365 (12)0.0029 (10)0.0028 (9)−0.0032 (10)
N40.0461 (13)0.0767 (18)0.0388 (13)0.0114 (12)0.0047 (10)−0.0105 (12)
O10.0381 (11)0.0840 (15)0.0489 (12)0.0018 (10)0.0061 (8)−0.0122 (11)
S10.0361 (4)0.0717 (5)0.0441 (4)−0.0058 (3)0.0064 (3)−0.0110 (4)

Geometric parameters (Å, °)

C1—C21.373 (5)C23—C281.382 (4)
C1—C61.385 (5)C23—N31.452 (3)
C1—C71.509 (4)C24—C251.380 (4)
C2—C31.378 (6)C24—H240.9300
C2—H20.9300C25—C261.366 (5)
C3—C41.345 (8)C25—H250.9300
C3—H30.9300C26—C271.352 (5)
C4—C51.343 (8)C26—F11.363 (3)
C4—H40.9300C27—C281.381 (4)
C5—C61.374 (7)C27—H270.9300
C5—H50.9300C28—H280.9300
C6—H60.9300C29—C301.485 (4)
C7—N11.489 (3)C29—N41.491 (4)
C7—C81.528 (4)C29—H29A0.9700
C7—H70.9800C29—H29B0.9700
C8—C91.488 (4)C30—C311.521 (4)
C8—H8A0.9700C30—H30A0.9700
C8—H8B0.9700C30—H30B0.9700
C9—C101.355 (3)C31—C321.491 (5)
C9—C191.439 (4)C31—H31A0.9700
C10—C121.501 (4)C31—H31B0.9700
C10—S11.741 (3)C32—H32A0.9600
C11—N11.468 (4)C32—H32B0.9600
C11—H11A0.9600C32—H32C0.9600
C11—H11B0.9600C33—C341.444 (9)
C11—H11C0.9600C33—N41.473 (4)
C12—N11.472 (3)C33—C34'1.585 (12)
C12—C131.525 (4)C33—H33A0.9700
C12—H120.9800C33—H33B0.9700
C13—C141.374 (4)C33—H33C0.9700
C13—C181.385 (5)C33—H33D0.9700
C14—C151.401 (5)C34—C351.506 (10)
C14—H140.9300C34—H34A0.9700
C15—C161.368 (6)C34—H34B0.9700
C15—H150.9300C35—C361.494 (10)
C16—C171.379 (6)C35—H35A0.9700
C16—H160.9300C35—H35B0.9700
C17—C181.371 (5)C36—H36A0.9600
C17—H170.9300C36—H36B0.9600
C18—H180.9300C36—H36C0.9600
C19—C201.373 (3)C35'—C36'1.496 (12)
C19—C211.428 (3)C35'—C34'1.517 (11)
C20—N21.366 (3)C35'—H35C0.9700
C20—S11.734 (3)C35'—H35D0.9700
C21—O11.217 (3)C36'—H36D0.9600
C21—N31.424 (3)C36'—H36E0.9600
C22—N21.301 (3)C36'—H36F0.9600
C22—N41.375 (3)C34'—H34C0.9700
C22—N31.395 (3)C34'—H34D0.9700
C23—C241.366 (4)
C2—C1—C6117.6 (4)C27—C26—F1118.6 (3)
C2—C1—C7121.9 (3)C27—C26—C25123.0 (3)
C6—C1—C7120.5 (3)F1—C26—C25118.3 (4)
C1—C2—C3120.4 (5)C26—C27—C28118.6 (3)
C1—C2—H2119.8C26—C27—H27120.7
C3—C2—H2119.8C28—C27—H27120.7
C4—C3—C2121.4 (6)C27—C28—C23119.6 (3)
C4—C3—H3119.3C27—C28—H28120.2
C2—C3—H3119.3C23—C28—H28120.2
C5—C4—C3118.9 (5)C30—C29—N4117.4 (3)
C5—C4—H4120.5C30—C29—H29A108.0
C3—C4—H4120.5N4—C29—H29A108.0
C4—C5—C6121.4 (6)C30—C29—H29B108.0
C4—C5—H5119.3N4—C29—H29B108.0
C6—C5—H5119.3H29A—C29—H29B107.2
C5—C6—C1120.3 (5)C29—C30—C31112.4 (3)
C5—C6—H6119.9C29—C30—H30A109.1
C1—C6—H6119.9C31—C30—H30A109.1
N1—C7—C1111.3 (2)C29—C30—H30B109.1
N1—C7—C8110.3 (2)C31—C30—H30B109.1
C1—C7—C8110.6 (2)H30A—C30—H30B107.9
N1—C7—H7108.2C32—C31—C30113.9 (3)
C1—C7—H7108.2C32—C31—H31A108.8
C8—C7—H7108.2C30—C31—H31A108.8
C9—C8—C7111.5 (2)C32—C31—H31B108.8
C9—C8—H8A109.3C30—C31—H31B108.8
C7—C8—H8A109.3H31A—C31—H31B107.7
C9—C8—H8B109.3C31—C32—H32A109.5
C7—C8—H8B109.3C31—C32—H32B109.5
H8A—C8—H8B108.0H32A—C32—H32B109.5
C10—C9—C19112.0 (2)C31—C32—H32C109.5
C10—C9—C8120.1 (2)H32A—C32—H32C109.5
C19—C9—C8127.9 (2)H32B—C32—H32C109.5
C9—C10—C12125.4 (2)C34—C33—N4124.2 (6)
C9—C10—S1112.6 (2)N4—C33—C34'106.1 (6)
C12—C10—S1121.97 (19)C34—C33—H33A106.3
N1—C11—H11A109.5N4—C33—H33A106.3
N1—C11—H11B109.5C34—C33—H33B106.3
H11A—C11—H11B109.5N4—C33—H33B106.3
N1—C11—H11C109.5H33A—C33—H33B106.4
H11A—C11—H11C109.5N4—C33—H33C110.9
H11B—C11—H11C109.5C34'—C33—H33C110.1
N1—C12—C10109.2 (2)N4—C33—H33D110.8
N1—C12—C13112.0 (2)C34'—C33—H33D110.2
C10—C12—C13109.5 (2)H33C—C33—H33D108.8
N1—C12—H12108.7C33—C34—C35115.1 (8)
C10—C12—H12108.7C33—C34—H34A108.5
C13—C12—H12108.7C35—C34—H34A108.5
C14—C13—C18119.1 (3)C33—C34—H34B108.5
C14—C13—C12119.9 (3)C35—C34—H34B108.5
C18—C13—C12120.9 (3)H34A—C34—H34B107.5
C13—C14—C15120.4 (4)C36—C35—C34111.1 (7)
C13—C14—H14119.8C36—C35—H35A109.4
C15—C14—H14119.8C34—C35—H35A109.4
C16—C15—C14119.3 (4)C36—C35—H35B109.4
C16—C15—H15120.3C34—C35—H35B109.4
C14—C15—H15120.3H35A—C35—H35B108.0
C15—C16—C17120.4 (4)C36'—C35'—C34'113.4 (10)
C15—C16—H16119.8C36'—C35'—H35C108.9
C17—C16—H16119.8C34'—C35'—H35C108.9
C18—C17—C16120.1 (4)C36'—C35'—H35D108.9
C18—C17—H17120.0C34'—C35'—H35D108.9
C16—C17—H17120.0H35C—C35'—H35D107.7
C17—C18—C13120.6 (4)C35'—C36'—H36D109.5
C17—C18—H18119.7C35'—C36'—H36E109.5
C13—C18—H18119.7H36D—C36'—H36E109.5
C20—C19—C21118.1 (2)C35'—C36'—H36F109.5
C20—C19—C9112.8 (2)H36D—C36'—H36F109.5
C21—C19—C9129.0 (2)H36E—C36'—H36F109.5
N2—C20—C19126.9 (2)C35'—C34'—C33112.1 (9)
N2—C20—S1121.52 (19)C35'—C34'—H34C109.2
C19—C20—S1111.6 (2)C33—C34'—H34C109.2
O1—C21—N3120.2 (2)C35'—C34'—H34D109.2
O1—C21—C19126.0 (2)C33—C34'—H34D109.2
N3—C21—C19113.8 (2)H34C—C34'—H34D107.9
N2—C22—N4120.1 (2)C11—N1—C12109.2 (2)
N2—C22—N3123.0 (2)C11—N1—C7110.4 (2)
N4—C22—N3116.8 (2)C12—N1—C7110.2 (2)
C24—C23—C28120.5 (3)C22—N2—C20115.6 (2)
C24—C23—N3120.0 (2)C22—N3—C21122.5 (2)
C28—C23—N3119.4 (3)C22—N3—C23122.3 (2)
C23—C24—C25120.0 (3)C21—N3—C23114.6 (2)
C23—C24—H24120.0C22—N4—C33118.2 (2)
C25—C24—H24120.0C22—N4—C29116.5 (2)
C26—C25—C24118.3 (3)C33—N4—C29117.4 (2)
C26—C25—H25120.9C20—S1—C1091.03 (12)
C24—C25—H25120.9
C6—C1—C2—C30.7 (6)C24—C25—C26—F1178.8 (3)
C7—C1—C2—C3−178.7 (4)F1—C26—C27—C28−179.4 (3)
C1—C2—C3—C40.7 (7)C25—C26—C27—C280.1 (6)
C2—C3—C4—C5−1.0 (9)C26—C27—C28—C23−0.2 (5)
C3—C4—C5—C60.0 (9)C24—C23—C28—C270.9 (5)
C4—C5—C6—C11.5 (8)N3—C23—C28—C27176.4 (3)
C2—C1—C6—C5−1.8 (5)N4—C29—C30—C31178.4 (3)
C7—C1—C6—C5177.7 (4)C29—C30—C31—C32178.4 (4)
C2—C1—C7—N156.1 (4)N4—C33—C34—C35−172.7 (8)
C6—C1—C7—N1−123.3 (3)C34'—C33—C34—C35157 (5)
C2—C1—C7—C8−66.9 (4)C33—C34—C35—C36179.6 (12)
C6—C1—C7—C8113.7 (3)C36'—C35'—C34'—C3378.0 (18)
N1—C7—C8—C946.5 (3)C34—C33—C34'—C35'−25 (3)
C1—C7—C8—C9170.1 (3)N4—C33—C34'—C35'−179.7 (10)
C7—C8—C9—C10−14.1 (4)C10—C12—N1—C11172.2 (3)
C7—C8—C9—C19166.6 (3)C13—C12—N1—C11−66.3 (3)
C19—C9—C10—C12179.6 (2)C10—C12—N1—C750.8 (3)
C8—C9—C10—C120.3 (4)C13—C12—N1—C7172.3 (2)
C19—C9—C10—S10.3 (3)C1—C7—N1—C1148.7 (3)
C8—C9—C10—S1−179.0 (2)C8—C7—N1—C11171.9 (3)
C9—C10—C12—N1−18.6 (4)C1—C7—N1—C12169.4 (2)
S1—C10—C12—N1160.7 (2)C8—C7—N1—C12−67.5 (3)
C9—C10—C12—C13−141.6 (3)N4—C22—N2—C20177.8 (2)
S1—C10—C12—C1337.6 (3)N3—C22—N2—C200.5 (4)
N1—C12—C13—C14137.7 (3)C19—C20—N2—C220.6 (4)
C10—C12—C13—C14−100.9 (3)S1—C20—N2—C22179.5 (2)
N1—C12—C13—C18−45.9 (4)N2—C22—N3—C210.1 (4)
C10—C12—C13—C1875.4 (3)N4—C22—N3—C21−177.3 (2)
C18—C13—C14—C15−1.0 (5)N2—C22—N3—C23170.3 (3)
C12—C13—C14—C15175.4 (3)N4—C22—N3—C23−7.1 (4)
C13—C14—C15—C160.3 (5)O1—C21—N3—C22176.8 (3)
C14—C15—C16—C170.6 (6)C19—C21—N3—C22−1.6 (4)
C15—C16—C17—C18−0.9 (6)O1—C21—N3—C235.9 (4)
C16—C17—C18—C130.2 (5)C19—C21—N3—C23−172.5 (2)
C14—C13—C18—C170.7 (5)C24—C23—N3—C22−64.1 (4)
C12—C13—C18—C17−175.6 (3)C28—C23—N3—C22120.4 (3)
C10—C9—C19—C20−0.8 (3)C24—C23—N3—C21106.9 (3)
C8—C9—C19—C20178.5 (3)C28—C23—N3—C21−68.6 (3)
C10—C9—C19—C21−178.4 (3)N2—C22—N4—C33119.2 (3)
C8—C9—C19—C210.9 (5)N3—C22—N4—C33−63.3 (4)
C21—C19—C20—N2−2.2 (4)N2—C22—N4—C29−29.2 (4)
C9—C19—C20—N2180.0 (3)N3—C22—N4—C29148.3 (3)
C21—C19—C20—S1178.8 (2)C34—C33—N4—C22138.2 (9)
C9—C19—C20—S11.0 (3)C34'—C33—N4—C22148.7 (8)
C20—C19—C21—O1−175.9 (3)C34—C33—N4—C29−73.7 (9)
C9—C19—C21—O11.5 (5)C34'—C33—N4—C29−63.2 (8)
C20—C19—C21—N32.5 (4)C30—C29—N4—C2285.0 (4)
C9—C19—C21—N3179.9 (2)C30—C29—N4—C33−63.7 (4)
C28—C23—C24—C25−1.5 (5)N2—C20—S1—C10−179.7 (2)
N3—C23—C24—C25−177.0 (3)C19—C20—S1—C10−0.7 (2)
C23—C24—C25—C261.3 (5)C9—C10—S1—C200.2 (2)
C24—C25—C26—C27−0.6 (6)C12—C10—S1—C20−179.2 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.932.473.304 (6)149

Symmetry codes: (i) −x+1, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2671).

References

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