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The asymmetric unit of the title compound, C26H19F2N3O2S, contains two independent mol­ecules. In one of the independent mol­ecules, the cyclo­hexene ring adopts a half-chair conformation, while in the other it is in an envelope conformation. In both mol­ecules, the thia­triaza­cyclo­penta[a]naphthalen-6-one ring system is approximately planar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041523/ci2179sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041523/ci2179Isup2.hkl
Contains datablock I

CCDC reference: 627452

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C)= 0.005 Å
  • R factor = 0.061
  • wR factor = 0.171
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

2-(3,5-Difluorophenoxy)-5-methyl-3-phenyl-8,9,10,11-tetrahydro- 4H-benzo[4',5']thieno[3',2':5,6]pyrido[4,3-d]pyrimidin- 4(3H)-one top
Crystal data top
C26H19F2N3O2SZ = 4
Mr = 475.50F(000) = 984
Triclinic, P1Dx = 1.366 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.8431 (12) ÅCell parameters from 3446 reflections
b = 13.2490 (14) Åθ = 2.2–21.1°
c = 15.0574 (16) ŵ = 0.19 mm1
α = 82.536 (2)°T = 298 K
β = 80.807 (2)°Block, colourless
γ = 88.738 (2)°0.30 × 0.20 × 0.13 mm
V = 2312.5 (4) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
9945 independent reflections
Radiation source: fine-focus sealed tube4588 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
φ and ω scansθmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1515
Tmin = 0.957, Tmax = 0.976k = 1616
21943 measured reflectionsl = 1919
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) = 0.171H-atom parameters constrained
S = 0.85 w = 1/[σ2(Fo2) + (0.0832P)2]
where P = (Fo2 + 2Fc2)/3
9945 reflections(Δ/σ)max = 0.002
634 parametersΔρmax = 0.25 e Å3
33 restraintsΔρmin = 0.30 e Å3
Special details top

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*/UeqOcc. (<1)
C11.1654 (2)0.0127 (2)0.11006 (17)0.0525 (7)
C21.2251 (2)0.1118 (2)0.1050 (2)0.0639 (8)
H2A1.20030.14130.16070.077*
H2B1.20380.15840.05520.077*
C31.3549 (3)0.0994 (3)0.0913 (3)0.0916 (11)
H3A1.38320.11280.02680.110*
H3B1.38630.15140.12010.110*
C41.4000 (3)0.0017 (4)0.1252 (3)0.1221 (16)
H4A1.48130.00070.10240.147*
H4B1.39140.00280.19070.147*
C51.3494 (2)0.0884 (3)0.1029 (3)0.0830 (10)
H5A1.36660.14710.14420.100*
H5B1.38220.10000.04180.100*
C61.2227 (2)0.0766 (2)0.1094 (2)0.0635 (8)
C71.0434 (2)0.00270 (19)0.11921 (17)0.0474 (6)
C81.0146 (2)0.10479 (19)0.12512 (17)0.0512 (7)
C90.8215 (2)0.0796 (2)0.14094 (18)0.0488 (6)
C100.7058 (2)0.1283 (2)0.1562 (2)0.0645 (8)
H10A0.66650.10470.10630.097*
H10B0.66240.11050.21150.097*
H10C0.71430.20090.16050.097*
C110.8396 (2)0.02782 (19)0.13281 (17)0.0484 (6)
C120.9514 (2)0.06658 (19)0.12147 (17)0.0478 (6)
C130.8899 (2)0.2292 (2)0.1138 (2)0.0614 (8)
C140.7446 (2)0.0993 (2)0.1362 (2)0.0571 (7)
C151.0139 (2)0.3710 (2)0.0776 (2)0.0652 (8)
C161.0471 (3)0.4348 (2)0.1325 (2)0.0806 (10)
H161.00030.44770.18560.097*
C171.1534 (3)0.4793 (2)0.1057 (3)0.0894 (11)
C181.2229 (3)0.4644 (2)0.0282 (3)0.0834 (11)
H181.29350.49650.01110.100*
C191.1842 (3)0.4002 (2)0.0233 (3)0.0781 (10)
C201.0814 (3)0.3526 (2)0.0022 (2)0.0760 (9)
H201.05760.30950.03970.091*
C210.6855 (2)0.2784 (2)0.1333 (2)0.0663 (8)
C220.6633 (3)0.3268 (3)0.2101 (3)0.0871 (11)
H220.70700.31230.25630.105*
C230.5752 (4)0.3972 (3)0.2176 (4)0.1104 (14)
H230.56020.43180.26820.133*
C240.5109 (3)0.4151 (3)0.1496 (4)0.1122 (17)
H240.45140.46200.15460.135*
C250.5321 (3)0.3655 (3)0.0741 (3)0.1029 (13)
H250.48670.37800.02890.124*
C260.6211 (3)0.2970 (2)0.0659 (3)0.0798 (10)
H260.63710.26380.01450.096*
C270.1630 (3)1.2070 (3)0.3546 (2)0.0777 (9)
C280.2695 (4)1.2704 (3)0.3482 (3)0.1047 (13)
H28A0.29791.29360.28500.126*0.569 (12)
H28B0.25011.33000.37880.126*0.569 (12)
H28C0.27471.32370.29740.126*0.431 (12)
H28D0.26831.30040.40310.126*0.431 (12)
C290.3606 (7)1.2125 (6)0.3894 (8)0.095 (3)0.569 (12)
H29A0.34001.20200.45490.114*0.569 (12)
H29B0.43201.25000.37410.114*0.569 (12)
C300.3747 (7)1.1092 (8)0.3524 (8)0.081 (3)0.569 (12)
H30A0.43741.07240.37620.097*0.569 (12)
H30B0.39481.12110.28690.097*0.569 (12)
C29'0.3720 (8)1.2030 (7)0.3307 (10)0.100 (4)0.431 (12)
H29C0.43971.24060.33550.119*0.431 (12)
H29D0.37951.18750.26880.119*0.431 (12)
C30'0.3691 (11)1.1020 (10)0.3947 (11)0.090 (5)0.431 (12)
H30C0.35951.11480.45750.108*0.431 (12)
H30D0.43951.06420.38130.108*0.431 (12)
C310.2658 (2)1.0421 (2)0.3773 (2)0.0734 (9)
H31A0.27190.98800.33910.088*0.569 (12)
H31B0.25941.01110.43990.088*0.569 (12)
H31C0.29211.01280.32350.088*0.431 (12)
H31D0.24520.98890.42720.088*0.431 (12)
C320.1611 (2)1.1039 (2)0.36501 (19)0.0598 (7)
C330.0486 (2)1.0656 (2)0.36616 (17)0.0535 (7)
C340.0313 (3)1.1432 (2)0.3574 (2)0.0674 (8)
C350.1851 (2)1.0381 (2)0.36539 (19)0.0609 (8)
C360.3117 (2)1.0317 (3)0.3684 (2)0.0780 (9)
H36A0.34261.09910.35860.117*
H36B0.34610.99870.42670.117*
H36C0.32750.99330.32200.117*
C370.1107 (2)0.9526 (2)0.37054 (18)0.0540 (7)
C380.0073 (2)0.9660 (2)0.37102 (17)0.0510 (7)
C390.0438 (2)0.7978 (2)0.37525 (19)0.0556 (7)
C400.1538 (2)0.8488 (2)0.37534 (18)0.0570 (7)
C410.2303 (2)0.7283 (2)0.3699 (2)0.0580 (7)
C420.2765 (3)0.7668 (2)0.4364 (2)0.0774 (9)
H420.23050.78740.48690.093*
C430.3930 (3)0.7734 (3)0.4253 (3)0.0865 (11)
C440.4649 (3)0.7418 (3)0.3538 (3)0.0875 (11)
H440.54390.74770.34780.105*
C450.4143 (3)0.7018 (3)0.2927 (3)0.0813 (10)
C460.2980 (3)0.6937 (2)0.2977 (2)0.0719 (9)
H460.26650.66580.25360.086*
C470.1041 (2)0.6680 (2)0.3773 (2)0.0594 (8)
C480.1398 (2)0.6393 (2)0.3027 (2)0.0689 (8)
H480.13790.68510.25010.083*
C490.1790 (3)0.5409 (3)0.3062 (3)0.0842 (10)
H490.20340.52050.25550.101*
C500.1822 (3)0.4744 (3)0.3822 (3)0.0958 (12)
H500.20980.40880.38430.115*
C510.1446 (3)0.5037 (3)0.4566 (3)0.1045 (13)
H510.14540.45700.50840.125*
C520.1060 (3)0.6004 (3)0.4558 (2)0.0824 (10)
H520.08160.62020.50670.099*
F11.1880 (2)0.5440 (2)0.1584 (2)0.1679 (12)
F21.2538 (2)0.38220 (18)0.09971 (17)0.1294 (9)
F30.44001 (18)0.8134 (2)0.4878 (2)0.1534 (11)
F40.48222 (18)0.6688 (2)0.22030 (17)0.1357 (9)
N10.90847 (18)0.14441 (16)0.13628 (15)0.0541 (6)
N20.97453 (18)0.16928 (16)0.11163 (16)0.0562 (6)
N30.77646 (17)0.20300 (16)0.12754 (16)0.0599 (6)
N40.1453 (2)1.1331 (2)0.35725 (18)0.0727 (7)
N50.08363 (17)0.88634 (17)0.37372 (15)0.0541 (6)
N60.06783 (17)0.77231 (16)0.37620 (15)0.0554 (6)
O10.64353 (15)0.07934 (14)0.14598 (16)0.0775 (6)
O20.90296 (16)0.33166 (14)0.10255 (16)0.0821 (7)
O30.25186 (16)0.82396 (16)0.37831 (15)0.0752 (6)
O40.11221 (15)0.71443 (14)0.37613 (14)0.0670 (6)
S11.13454 (6)0.18204 (6)0.11948 (6)0.0718 (3)
S20.03047 (9)1.26163 (7)0.34672 (8)0.1010 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0431 (15)0.0674 (19)0.0458 (17)0.0121 (13)0.0077 (12)0.0003 (14)
C20.0455 (15)0.077 (2)0.068 (2)0.0191 (14)0.0016 (14)0.0098 (16)
C30.057 (2)0.097 (3)0.118 (3)0.0270 (19)0.0235 (19)0.010 (2)
C40.052 (2)0.134 (4)0.190 (4)0.000 (2)0.022 (2)0.052 (3)
C50.0465 (17)0.087 (2)0.111 (3)0.0059 (16)0.0153 (17)0.010 (2)
C60.0470 (16)0.070 (2)0.072 (2)0.0041 (14)0.0145 (14)0.0022 (16)
C70.0427 (14)0.0547 (16)0.0445 (16)0.0085 (12)0.0088 (12)0.0010 (12)
C80.0488 (15)0.0531 (16)0.0512 (18)0.0056 (12)0.0127 (12)0.0025 (13)
C90.0425 (14)0.0520 (16)0.0520 (17)0.0090 (12)0.0111 (12)0.0011 (13)
C100.0489 (16)0.0529 (17)0.093 (2)0.0134 (13)0.0174 (15)0.0056 (16)
C110.0415 (14)0.0486 (15)0.0544 (18)0.0082 (12)0.0087 (12)0.0010 (12)
C120.0418 (14)0.0535 (16)0.0472 (17)0.0105 (12)0.0081 (12)0.0002 (12)
C130.0494 (17)0.0500 (17)0.081 (2)0.0145 (14)0.0026 (15)0.0023 (15)
C140.0437 (16)0.0521 (17)0.074 (2)0.0117 (13)0.0087 (14)0.0001 (14)
C150.0493 (17)0.0386 (15)0.103 (3)0.0088 (13)0.0076 (17)0.0019 (16)
C160.079 (2)0.0566 (19)0.103 (3)0.0080 (17)0.0020 (19)0.0171 (18)
C170.086 (3)0.061 (2)0.130 (4)0.0180 (19)0.027 (2)0.029 (2)
C180.060 (2)0.057 (2)0.129 (3)0.0170 (16)0.008 (2)0.001 (2)
C190.068 (2)0.062 (2)0.094 (3)0.0139 (17)0.0091 (19)0.0023 (19)
C200.073 (2)0.064 (2)0.089 (3)0.0252 (17)0.0098 (19)0.0036 (18)
C210.0436 (16)0.0516 (17)0.099 (3)0.0108 (14)0.0013 (17)0.0035 (17)
C220.071 (2)0.077 (2)0.111 (3)0.0036 (19)0.000 (2)0.020 (2)
C230.083 (3)0.092 (3)0.151 (4)0.000 (2)0.016 (3)0.036 (3)
C240.063 (2)0.065 (2)0.195 (6)0.001 (2)0.017 (3)0.011 (3)
C250.064 (2)0.065 (2)0.175 (5)0.0017 (19)0.023 (2)0.009 (3)
C260.0558 (19)0.060 (2)0.121 (3)0.0018 (16)0.014 (2)0.0017 (19)
C270.085 (2)0.070 (2)0.080 (2)0.0151 (18)0.0209 (18)0.0087 (17)
C280.117 (3)0.083 (3)0.115 (3)0.036 (3)0.017 (3)0.011 (2)
C290.085 (5)0.110 (6)0.090 (6)0.037 (4)0.020 (4)0.005 (5)
C300.069 (4)0.091 (6)0.086 (7)0.022 (4)0.016 (4)0.014 (5)
C29'0.096 (6)0.100 (7)0.101 (8)0.041 (5)0.015 (6)0.001 (6)
C30'0.075 (6)0.095 (7)0.102 (9)0.018 (5)0.014 (6)0.016 (6)
C310.0602 (19)0.081 (2)0.078 (2)0.0168 (17)0.0073 (16)0.0080 (18)
C320.0657 (19)0.0606 (19)0.0538 (19)0.0079 (15)0.0126 (14)0.0049 (14)
C330.0596 (17)0.0561 (17)0.0449 (17)0.0024 (14)0.0091 (13)0.0057 (13)
C340.077 (2)0.0589 (19)0.070 (2)0.0026 (16)0.0214 (17)0.0126 (16)
C350.0626 (18)0.068 (2)0.057 (2)0.0097 (16)0.0165 (14)0.0164 (15)
C360.0600 (19)0.092 (2)0.089 (3)0.0217 (17)0.0255 (17)0.0251 (19)
C370.0537 (16)0.0591 (17)0.0499 (18)0.0032 (14)0.0099 (13)0.0076 (13)
C380.0499 (16)0.0570 (17)0.0457 (17)0.0007 (13)0.0101 (12)0.0019 (13)
C390.0449 (15)0.0593 (18)0.061 (2)0.0018 (14)0.0097 (13)0.0007 (14)
C400.0473 (16)0.070 (2)0.0539 (19)0.0003 (14)0.0114 (13)0.0067 (15)
C410.0489 (16)0.0462 (16)0.077 (2)0.0016 (13)0.0126 (15)0.0018 (15)
C420.062 (2)0.086 (2)0.087 (3)0.0075 (17)0.0132 (18)0.023 (2)
C430.061 (2)0.096 (3)0.115 (3)0.0071 (18)0.037 (2)0.036 (2)
C440.0490 (19)0.090 (3)0.123 (3)0.0025 (18)0.010 (2)0.016 (2)
C450.067 (2)0.086 (2)0.088 (3)0.0131 (19)0.000 (2)0.016 (2)
C460.064 (2)0.066 (2)0.088 (3)0.0038 (16)0.0178 (18)0.0127 (18)
C470.0464 (15)0.0544 (17)0.076 (2)0.0071 (13)0.0108 (15)0.0005 (16)
C480.0692 (19)0.069 (2)0.068 (2)0.0130 (16)0.0142 (16)0.0025 (17)
C490.084 (2)0.072 (2)0.099 (3)0.0190 (19)0.019 (2)0.013 (2)
C500.094 (3)0.056 (2)0.136 (4)0.0219 (19)0.025 (3)0.005 (2)
C510.119 (3)0.084 (3)0.106 (3)0.035 (2)0.039 (3)0.037 (2)
C520.093 (2)0.076 (2)0.078 (3)0.0247 (19)0.0283 (19)0.0120 (19)
F10.155 (2)0.156 (2)0.211 (3)0.0646 (19)0.020 (2)0.092 (2)
F20.1213 (18)0.1280 (19)0.121 (2)0.0478 (15)0.0415 (15)0.0180 (15)
F30.0865 (15)0.217 (3)0.192 (3)0.0190 (16)0.0610 (16)0.116 (2)
F40.0898 (15)0.178 (2)0.137 (2)0.0182 (15)0.0124 (14)0.0562 (19)
N10.0443 (12)0.0508 (13)0.0675 (16)0.0084 (10)0.0137 (11)0.0017 (11)
N20.0419 (12)0.0465 (13)0.0779 (17)0.0091 (11)0.0068 (11)0.0013 (11)
N30.0386 (12)0.0501 (14)0.0879 (19)0.0061 (10)0.0039 (11)0.0041 (12)
N40.0753 (18)0.0701 (18)0.0799 (19)0.0162 (14)0.0280 (14)0.0201 (14)
N50.0447 (12)0.0527 (14)0.0641 (16)0.0034 (11)0.0113 (11)0.0004 (11)
N60.0444 (12)0.0544 (14)0.0674 (16)0.0052 (11)0.0127 (11)0.0024 (11)
O10.0407 (11)0.0618 (13)0.1280 (19)0.0094 (9)0.0173 (11)0.0012 (12)
O20.0486 (11)0.0473 (12)0.143 (2)0.0105 (9)0.0007 (12)0.0020 (12)
O30.0442 (11)0.0851 (15)0.0979 (17)0.0065 (10)0.0137 (11)0.0129 (12)
O40.0472 (11)0.0523 (11)0.1013 (17)0.0011 (9)0.0168 (10)0.0025 (11)
S10.0491 (4)0.0610 (5)0.1040 (7)0.0001 (4)0.0169 (4)0.0000 (4)
S20.1153 (8)0.0557 (5)0.1417 (10)0.0006 (5)0.0461 (7)0.0173 (6)
Geometric parameters (Å, º) top
C1—C61.351 (4)C28—H28B0.97
C1—C71.445 (3)C28—H28C0.97
C1—C21.494 (4)C28—H28D0.96
C2—C31.527 (4)C29—C301.539 (8)
C2—H2A0.97C29—H29A0.97
C2—H2B0.97C29—H29B0.97
C3—C41.451 (5)C30—C311.551 (6)
C3—H3A0.97C30—H30A0.97
C3—H3B0.97C30—H30B0.97
C4—C51.448 (5)C29'—C30'1.542 (9)
C4—H4A0.97C29'—H29C0.97
C4—H4B0.97C29'—H29D0.97
C5—C61.494 (4)C30'—C311.548 (8)
C5—H5A0.97C30'—H30C0.97
C5—H5B0.97C30'—H30D0.97
C6—S11.739 (3)C31—C321.493 (4)
C7—C81.391 (3)C31—H31A0.97
C7—C121.408 (3)C31—H31B0.97
C8—N11.349 (3)C31—H31C0.95
C8—S11.730 (3)C31—H31D0.96
C9—N11.325 (3)C32—C331.433 (4)
C9—C111.431 (3)C33—C341.390 (4)
C9—C101.499 (3)C33—C381.405 (3)
C10—H10A0.96C34—N41.359 (4)
C10—H10B0.96C34—S21.724 (3)
C10—H10C0.96C35—N41.338 (4)
C11—C121.407 (3)C35—C371.421 (4)
C11—C141.454 (3)C35—C361.496 (4)
C12—N21.378 (3)C36—H36A0.96
C13—N21.264 (3)C36—H36B0.96
C13—O21.356 (3)C36—H36C0.96
C13—N31.371 (3)C37—C381.415 (3)
C14—O11.214 (3)C37—C401.466 (4)
C14—N31.416 (3)C38—N51.376 (3)
C15—C161.361 (4)C39—N51.270 (3)
C15—C201.379 (4)C39—O41.355 (3)
C15—O21.400 (3)C39—N61.369 (3)
C16—C171.381 (4)C40—O31.206 (3)
C16—H160.93C40—N61.421 (3)
C17—C181.349 (5)C41—C461.367 (4)
C17—F11.352 (4)C41—C421.372 (4)
C18—C191.356 (4)C41—O41.401 (3)
C18—H180.93C42—C431.367 (4)
C19—F21.348 (4)C42—H420.93
C19—C201.357 (4)C43—F31.337 (4)
C20—H200.93C43—C441.366 (4)
C21—C261.359 (4)C44—C451.343 (4)
C21—C221.380 (4)C44—H440.93
C21—N31.453 (3)C45—F41.363 (4)
C22—C231.385 (5)C45—C461.373 (4)
C22—H220.93C46—H460.93
C23—C241.364 (6)C47—C481.362 (4)
C23—H230.93C47—C521.385 (4)
C24—C251.372 (6)C47—N61.453 (3)
C24—H240.93C48—C491.386 (4)
C25—C261.376 (4)C48—H480.93
C25—H250.93C49—C501.347 (5)
C26—H260.93C49—H490.93
C27—C321.355 (4)C50—C511.372 (5)
C27—C281.515 (5)C50—H500.93
C27—S21.728 (3)C51—C521.368 (4)
C28—C291.480 (7)C51—H510.93
C28—C29'1.500 (8)C52—H520.93
C28—H28A0.97
C6—C1—C7111.4 (2)H29A—C29—H29B108.4
C6—C1—C2122.0 (2)C29—C30—C31113.5 (6)
C7—C1—C2126.5 (3)C29—C30—H30A108.9
C1—C2—C3112.0 (3)C31—C30—H30A108.9
C1—C2—H2A109.2C29—C30—H30B108.9
C3—C2—H2A109.2C31—C30—H30B108.9
C1—C2—H2B109.2H30A—C30—H30B107.7
C3—C2—H2B109.2C28—C29'—C30'115.2 (11)
H2A—C2—H2B107.9C28—C29'—H29C108.5
C4—C3—C2117.2 (3)C30'—C29'—H29C108.5
C4—C3—H3A108.0C28—C29'—H29D108.5
C2—C3—H3A108.0C30'—C29'—H29D108.5
C4—C3—H3B108.0H29C—C29'—H29D107.5
C2—C3—H3B108.0C29'—C30'—C31105.7 (8)
H3A—C3—H3B107.2C29'—C30'—H30C110.6
C5—C4—C3117.1 (3)C31—C30'—H30C110.6
C5—C4—H4A108.0C29'—C30'—H30D110.6
C3—C4—H4A108.0C31—C30'—H30D110.6
C5—C4—H4B108.0H30C—C30'—H30D108.7
C3—C4—H4B108.0C32—C31—C30'115.5 (6)
H4A—C4—H4B107.3C32—C31—C30111.0 (5)
C4—C5—C6110.7 (3)C32—C31—H31A109.4
C4—C5—H5A109.5C30'—C31—H31A124.1
C6—C5—H5A109.5C30—C31—H31A109.4
C4—C5—H5B109.5C32—C31—H31B109.4
C6—C5—H5B109.5C30'—C31—H31B86.9
H5A—C5—H5B108.1C30—C31—H31B109.4
C1—C6—C5125.3 (3)H31A—C31—H31B108.0
C1—C6—S1113.7 (2)C32—C31—H31C109.2
C5—C6—S1121.0 (2)C30'—C31—H31C105.2
C8—C7—C12115.8 (2)C30—C31—H31C86.3
C8—C7—C1112.5 (2)H31B—C31—H31C128.8
C12—C7—C1131.6 (2)C32—C31—H31D107.9
N1—C8—C7127.1 (2)C30'—C31—H31D109.3
N1—C8—S1121.3 (2)C30—C31—H31D129.7
C7—C8—S1111.57 (19)H31A—C31—H31D85.6
N1—C9—C11121.4 (2)H31C—C31—H31D109.7
N1—C9—C10114.7 (2)C27—C32—C33111.8 (3)
C11—C9—C10124.0 (2)C27—C32—C31121.7 (3)
C9—C10—H10A109.5C33—C32—C31126.5 (3)
C9—C10—H10B109.5C34—C33—C38115.9 (2)
H10A—C10—H10B109.5C34—C33—C32112.2 (3)
C9—C10—H10C109.5C38—C33—C32131.8 (3)
H10A—C10—H10C109.5N4—C34—C33127.3 (3)
H10B—C10—H10C109.5N4—C34—S2121.0 (2)
C12—C11—C9120.0 (2)C33—C34—S2111.7 (2)
C12—C11—C14118.4 (2)N4—C35—C37121.4 (3)
C9—C11—C14121.6 (2)N4—C35—C36114.1 (3)
N2—C12—C11122.8 (2)C37—C35—C36124.5 (3)
N2—C12—C7118.8 (2)C35—C36—H36A109.5
C11—C12—C7118.4 (2)C35—C36—H36B109.5
N2—C13—O2121.9 (2)H36A—C36—H36B109.5
N2—C13—N3127.0 (2)C35—C36—H36C109.5
O2—C13—N3111.1 (2)H36A—C36—H36C109.5
O1—C14—N3118.0 (2)H36B—C36—H36C109.5
O1—C14—C11127.1 (2)C38—C37—C35120.4 (3)
N3—C14—C11114.8 (2)C38—C37—C40118.4 (2)
C16—C15—C20122.2 (3)C35—C37—C40121.2 (2)
C16—C15—O2116.2 (3)N5—C38—C33118.7 (2)
C20—C15—O2121.4 (3)N5—C38—C37122.9 (2)
C15—C16—C17116.8 (3)C33—C38—C37118.3 (2)
C15—C16—H16121.6N5—C39—O4121.5 (2)
C17—C16—H16121.6N5—C39—N6127.1 (3)
C18—C17—F1118.3 (3)O4—C39—N6111.4 (2)
C18—C17—C16123.5 (3)O3—C40—N6119.0 (3)
F1—C17—C16118.1 (4)O3—C40—C37126.8 (3)
C17—C18—C19116.4 (3)N6—C40—C37114.2 (2)
C17—C18—H18121.8C46—C41—C42121.4 (3)
C19—C18—H18121.8C46—C41—O4116.5 (3)
F2—C19—C18117.3 (3)C42—C41—O4121.9 (3)
F2—C19—C20118.5 (3)C43—C42—C41117.1 (3)
C18—C19—C20124.2 (3)C43—C42—H42121.4
C19—C20—C15116.8 (3)C41—C42—H42121.4
C19—C20—H20121.6F3—C43—C44117.7 (3)
C15—C20—H20121.6F3—C43—C42118.3 (3)
C26—C21—C22121.2 (3)C44—C43—C42124.0 (3)
C26—C21—N3120.2 (3)C45—C44—C43115.8 (3)
C22—C21—N3118.5 (3)C45—C44—H44122.1
C21—C22—C23119.3 (4)C43—C44—H44122.1
C21—C22—H22120.3C44—C45—F4118.1 (3)
C23—C22—H22120.3C44—C45—C46124.1 (3)
C24—C23—C22118.9 (4)F4—C45—C46117.8 (3)
C24—C23—H23120.5C41—C46—C45117.4 (3)
C22—C23—H23120.5C41—C46—H46121.3
C23—C24—C25121.5 (4)C45—C46—H46121.3
C23—C24—H24119.2C48—C47—C52121.0 (3)
C25—C24—H24119.2C48—C47—N6119.8 (3)
C24—C25—C26119.5 (4)C52—C47—N6119.2 (3)
C24—C25—H25120.3C47—C48—C49119.1 (3)
C26—C25—H25120.3C47—C48—H48120.5
C21—C26—C25119.5 (4)C49—C48—H48120.5
C21—C26—H26120.3C50—C49—C48120.6 (3)
C25—C26—H26120.3C50—C49—H49119.7
C32—C27—C28124.5 (3)C48—C49—H49119.7
C32—C27—S2113.3 (2)C49—C50—C51119.8 (3)
C28—C27—S2122.1 (3)C49—C50—H50120.1
C29—C28—C27112.0 (4)C51—C50—H50120.1
C29'—C28—C27108.3 (5)C52—C51—C50121.1 (3)
C29—C28—H28A109.2C52—C51—H51119.4
C29'—C28—H28A78.5C50—C51—H51119.4
C27—C28—H28A109.2C51—C52—C47118.3 (3)
C29—C28—H28B109.2C51—C52—H52120.9
C29'—C28—H28B136.9C47—C52—H52120.9
C27—C28—H28B109.2C9—N1—C8117.1 (2)
H28A—C28—H28B107.9C13—N2—C12117.0 (2)
C29—C28—H28C130.4C13—N3—C14120.0 (2)
C29'—C28—H28C106.9C13—N3—C21122.4 (2)
C27—C28—H28C110.7C14—N3—C21117.7 (2)
C29—C28—H28D78.2C35—N4—C34116.6 (3)
C29'—C28—H28D111.5C39—N5—C38116.9 (2)
C27—C28—H28D110.0C39—N6—C40120.4 (2)
H28A—C28—H28D133.2C39—N6—C47122.5 (2)
H28C—C28—H28D109.3C40—N6—C47117.1 (2)
C28—C29—C30108.3 (8)C13—O2—C15118.1 (2)
C28—C29—H29A110.0C39—O4—C41118.4 (2)
C30—C29—H29A110.0C8—S1—C690.83 (13)
C28—C29—H29B110.0C34—S2—C2790.96 (15)
C30—C29—H29B110.0
C6—C1—C2—C34.8 (4)C34—C33—C38—N5175.7 (2)
C7—C1—C2—C3177.5 (3)C32—C33—C38—N51.4 (4)
C1—C2—C3—C427.4 (4)C34—C33—C38—C372.6 (4)
C2—C3—C4—C547.7 (6)C32—C33—C38—C37179.8 (3)
C3—C4—C5—C640.2 (5)C35—C37—C38—N5178.4 (2)
C7—C1—C6—C5178.6 (3)C40—C37—C38—N51.5 (4)
C2—C1—C6—C50.6 (5)C35—C37—C38—C330.1 (4)
C7—C1—C6—S10.1 (3)C40—C37—C38—C33179.8 (2)
C2—C1—C6—S1178.1 (2)C38—C37—C40—O3177.6 (3)
C4—C5—C6—C117.6 (5)C35—C37—C40—O32.4 (4)
C4—C5—C6—S1161.0 (3)C38—C37—C40—N62.5 (4)
C6—C1—C7—C80.0 (3)C35—C37—C40—N6177.4 (2)
C2—C1—C7—C8177.9 (3)C46—C41—C42—C432.9 (5)
C6—C1—C7—C12178.7 (3)O4—C41—C42—C43177.4 (3)
C2—C1—C7—C123.4 (5)C41—C42—C43—F3178.0 (3)
C12—C7—C8—N12.8 (4)C41—C42—C43—C441.7 (6)
C1—C7—C8—N1178.2 (2)F3—C43—C44—C45179.8 (3)
C12—C7—C8—S1178.86 (18)C42—C43—C44—C450.4 (6)
C1—C7—C8—S10.1 (3)C43—C44—C45—F4179.8 (3)
N1—C9—C11—C121.3 (4)C43—C44—C45—C461.6 (6)
C10—C9—C11—C12177.9 (3)C42—C41—C46—C452.0 (5)
N1—C9—C11—C14178.9 (2)O4—C41—C46—C45176.7 (3)
C10—C9—C11—C141.9 (4)C44—C45—C46—C410.4 (5)
C9—C11—C12—N2178.8 (2)F4—C45—C46—C41179.1 (3)
C14—C11—C12—N21.4 (4)C52—C47—C48—C490.3 (5)
C9—C11—C12—C70.5 (4)N6—C47—C48—C49177.1 (3)
C14—C11—C12—C7179.3 (2)C47—C48—C49—C500.2 (5)
C8—C7—C12—N2177.0 (2)C48—C49—C50—C511.0 (6)
C1—C7—C12—N21.7 (4)C49—C50—C51—C521.4 (6)
C8—C7—C12—C112.4 (4)C50—C51—C52—C470.9 (6)
C1—C7—C12—C11178.9 (3)C48—C47—C52—C510.1 (5)
C12—C11—C14—O1179.6 (3)N6—C47—C52—C51177.5 (3)
C9—C11—C14—O10.2 (5)C11—C9—N1—C81.1 (4)
C12—C11—C14—N30.1 (4)C10—C9—N1—C8178.2 (2)
C9—C11—C14—N3179.8 (2)C7—C8—N1—C91.0 (4)
C20—C15—C16—C171.2 (5)S1—C8—N1—C9179.2 (2)
O2—C15—C16—C17176.0 (3)O2—C13—N2—C12178.3 (3)
C15—C16—C17—C181.6 (5)N3—C13—N2—C121.9 (5)
C15—C16—C17—F1179.2 (3)C11—C12—N2—C130.5 (4)
F1—C17—C18—C19179.0 (3)C7—C12—N2—C13179.9 (3)
C16—C17—C18—C191.4 (6)N2—C13—N3—C143.4 (5)
C17—C18—C19—F2178.2 (3)O2—C13—N3—C14176.8 (2)
C17—C18—C19—C200.9 (5)N2—C13—N3—C21176.9 (3)
F2—C19—C20—C15178.4 (3)O2—C13—N3—C212.9 (4)
C18—C19—C20—C150.6 (5)O1—C14—N3—C13178.2 (3)
C16—C15—C20—C190.8 (5)C11—C14—N3—C132.2 (4)
O2—C15—C20—C19175.3 (3)O1—C14—N3—C211.5 (4)
C26—C21—C22—C231.3 (5)C11—C14—N3—C21178.1 (3)
N3—C21—C22—C23178.6 (3)C26—C21—N3—C13110.3 (3)
C21—C22—C23—C241.5 (5)C22—C21—N3—C1372.5 (4)
C22—C23—C24—C250.4 (6)C26—C21—N3—C1469.5 (4)
C23—C24—C25—C260.9 (6)C22—C21—N3—C14107.8 (3)
C22—C21—C26—C250.0 (5)C37—C35—N4—C342.2 (4)
N3—C21—C26—C25177.2 (3)C36—C35—N4—C34177.8 (3)
C24—C25—C26—C211.1 (5)C33—C34—N4—C350.9 (5)
C32—C27—C28—C2922.5 (7)S2—C34—N4—C35179.7 (2)
S2—C27—C28—C29158.9 (5)O4—C39—N5—C38178.7 (2)
C32—C27—C28—C29'14.7 (8)N6—C39—N5—C381.3 (4)
S2—C27—C28—C29'163.9 (6)C33—C38—N5—C39177.9 (2)
C29'—C28—C29—C3042.1 (8)C37—C38—N5—C390.4 (4)
C27—C28—C29—C3048.7 (9)N5—C39—N6—C400.1 (4)
C28—C29—C30—C3162.0 (13)O4—C39—N6—C40179.9 (2)
C29—C28—C29'—C30'52.6 (10)N5—C39—N6—C47179.5 (3)
C27—C28—C29'—C30'49.8 (13)O4—C39—N6—C470.4 (4)
C28—C29'—C30'—C3163.1 (19)O3—C40—N6—C39178.3 (3)
C29'—C30'—C31—C3240.6 (15)C37—C40—N6—C391.8 (4)
C29'—C30'—C31—C3043.4 (15)O3—C40—N6—C472.2 (4)
C29—C30—C31—C3243.3 (11)C37—C40—N6—C47177.6 (2)
C29—C30—C31—C30'62.7 (19)C48—C47—N6—C39110.3 (3)
C28—C27—C32—C33178.3 (3)C52—C47—N6—C3972.3 (4)
S2—C27—C32—C330.5 (4)C48—C47—N6—C4069.2 (3)
C28—C27—C32—C314.0 (5)C52—C47—N6—C40108.3 (3)
S2—C27—C32—C31177.2 (2)N2—C13—O2—C157.3 (5)
C30'—C31—C32—C2710.6 (8)N3—C13—O2—C15172.9 (3)
C30—C31—C32—C2714.2 (6)C16—C15—O2—C13124.9 (3)
C30'—C31—C32—C33166.7 (7)C20—C15—O2—C1360.3 (4)
C30—C31—C32—C33168.5 (5)N5—C39—O4—C413.7 (4)
C27—C32—C33—C340.7 (4)N6—C39—O4—C41176.3 (2)
C31—C32—C33—C34176.9 (3)C46—C41—O4—C39120.4 (3)
C27—C32—C33—C38176.6 (3)C42—C41—O4—C3964.9 (4)
C31—C32—C33—C385.9 (5)N1—C8—S1—C6178.3 (2)
C38—C33—C34—N43.4 (4)C7—C8—S1—C60.1 (2)
C32—C33—C34—N4178.9 (3)C1—C6—S1—C80.1 (2)
C38—C33—C34—S2177.2 (2)C5—C6—S1—C8178.7 (3)
C32—C33—C34—S20.6 (3)N4—C34—S2—C27179.3 (3)
N4—C35—C37—C382.7 (4)C33—C34—S2—C270.3 (2)
C36—C35—C37—C38177.3 (3)C32—C27—S2—C340.1 (3)
N4—C35—C37—C40177.2 (3)C28—C27—S2—C34178.6 (3)
C36—C35—C37—C402.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O1i0.972.423.159 (4)132
C29—H29A···O3ii0.972.543.504 (12)170
Symmetry codes: (i) x+1, y, z; (ii) x, y+2, z+1.
 

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