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In the title N,S-substituted compound, C20H16Cl4FN3O2S, the piperazine ring adopts a chair conformation. The butadiene unit assumes a configuration close to cisoid.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022483/ac2026sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022483/ac2026Isup2.hkl
Contains datablock I

CCDC reference: 614853

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.040
  • wR factor = 0.118
  • Data-to-parameter ratio = 21.4

checkCIF/PLATON results

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Alert level C PLAT021_ALERT_1_C Ratio Unique / Expected Reflections too High ... 1.05 PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.01 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

3,4,4-Trichloro-1-(4-chlorophenylsulfanyl)-1-[4-(2-fluorophenyl)piperazinyl]- 2-nitrobuta-1,3-diene top
Crystal data top
C20H16Cl4FN3O2SF(000) = 1064.00
Mr = 523.24Dx = 1.552 Mg m3
Monoclinic, P21/nMelting point = 461–462 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.7107 Å
a = 13.7862 (4) ÅCell parameters from 18322 reflections
b = 11.0663 (3) Åθ = 2.3–30.0°
c = 14.6971 (4) ŵ = 0.65 mm1
β = 93.277 (1)°T = 294 K
V = 2238.56 (11) Å3Prism, yellow
Z = 40.50 × 0.40 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID S
diffractometer
6335 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.035
ω scansθmax = 30.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1919
Tmin = 0.682, Tmax = 0.878k = 1515
131970 measured reflectionsl = 2020
6892 independent reflections
Refinement top
Refinement on FH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040 Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 5.3958 -5.3010 2.8963
wR(F2) = 0.118(Δ/σ)max = 0.006
S = 1.09Δρmax = 0.93 e Å3
6335 reflectionsΔρmin = 0.56 e Å3
296 parameters
Special details top

Geometry. Least Squares Planes

————– Plane number 1 —————

Atoms Defining Plane Distance e.s.d. C1 [1;0;0;0] 0.1333 0.0008 C2 [1;0;0;0] -0.2659 0.0015 C3 [1;0;0;0] 0.2006 0.0012 C4 [1;0;0;0] -0.0809 0.0005

Additional Atoms Distance e.s.d.

Mean deviation from plane is 0.1702 angstrom Chi-squared: 29463.053

————– Plane number 2 —————

Atoms Defining Plane Distance e.s.d. C5 [1;0;0;0] -0.0209 0.0014 C6 [1;0;0;0] 0.0198 0.0015 C7 [1;0;0;0] -0.0039 0.0017 C8 [1;0;0;0] -0.0130 0.0018 C9 [1;0;0;0] 0.0101 0.0021 C10 [1;0;0;0] 0.0144 0.0019

Additional Atoms Distance e.s.d.

Mean deviation from plane is 0.0137 angstrom Chi-squared: 217.503

————– Plane number 3 —————

Atoms Defining Plane Distance e.s.d. C11 [1;0;0;0] 0.0119 0.0012 C12 [1;0;0;0] -0.0109 0.0011 C13 [1;0;0;0] 0.0088 0.0009 C14 [1;0;0;0] -0.0094 0.0010

Additional Atoms Distance e.s.d.

Mean deviation from plane is 0.0103 angstrom Chi-squared: 92.158

————– Plane number 4 —————

Atoms Defining Plane Distance e.s.d. C15 [1;0;0;0] -0.0151 0.0014 C16 [1;0;0;0] 0.0153 0.0018 C17 [1;0;0;0] 0.0025 0.0020 C18 [1;0;0;0] -0.0150 0.0018 C19 [1;0;0;0] 0.0068 0.0017 C20 [1;0;0;0] 0.0074 0.0014

Additional Atoms Distance e.s.d.

Mean deviation from plane is 0.0103 angstrom Chi-squared: 141.555

Dihedral angles between least-squares planes ——————————————–

plane plane angle e.s.d. 1 2 130.281 0.099 1 3 64.749 0.107 1 4 96.752 0.087 2 3 164.116 0.091 2 4 132.281 0.083 3 4 35.133 0.077

Refinement. Refinement using reflections with F2 > 3.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.17363 (4)0.15888 (6)0.54893 (4)0.0499 (2)
Cl10.34677 (5)0.13614 (6)0.55203 (5)0.0724 (2)
Cl20.32734 (7)0.14662 (7)0.74592 (7)0.0916 (3)
Cl30.35492 (6)0.12678 (6)0.76283 (4)0.0770 (2)
Cl40.06475 (6)0.06201 (8)0.21365 (5)0.0922 (3)
O20.46752 (11)0.2868 (2)0.52823 (11)0.0584 (5)
F10.45386 (10)0.1146 (2)0.11612 (10)0.0746 (5)
N30.30676 (11)0.1681 (2)0.22944 (11)0.0393 (4)
N20.30860 (12)0.1877 (2)0.42395 (11)0.0403 (4)
N10.45701 (12)0.1974 (2)0.57726 (12)0.0464 (5)
O10.52383 (12)0.1604 (2)0.63042 (12)0.0689 (6)
C120.3628 (2)0.0846 (2)0.29051 (13)0.0435 (6)
C130.2205 (1)0.2117 (2)0.27370 (13)0.0398 (5)
C150.2858 (2)0.1186 (2)0.14085 (13)0.0398 (5)
C30.3652 (1)0.1384 (2)0.57742 (13)0.0398 (5)
C50.1042 (1)0.0928 (2)0.4558 (1)0.0429 (6)
C40.2925 (1)0.1630 (2)0.51078 (13)0.0395 (5)
C110.3948 (1)0.1449 (2)0.38037 (13)0.0452 (6)
C200.1919 (2)0.0984 (2)0.10379 (13)0.0428 (6)
C60.1281 (2)0.0183 (2)0.4226 (1)0.0484 (6)
C140.2501 (2)0.2702 (2)0.36472 (13)0.0415 (5)
C80.0024 (2)0.0046 (2)0.3102 (2)0.0550 (7)
C10.3442 (2)0.0584 (2)0.6513 (2)0.0510 (7)
C20.3546 (2)0.0596 (2)0.6554 (1)0.0465 (6)
C70.0758 (2)0.0677 (2)0.3473 (2)0.0526 (7)
C160.3611 (2)0.0901 (2)0.0856 (1)0.0503 (6)
C190.1754 (2)0.0475 (2)0.0168 (1)0.0521 (7)
C180.2519 (2)0.0168 (2)0.0334 (2)0.0566 (7)
C170.3459 (2)0.0391 (2)0.0005 (2)0.0606 (8)
C100.0233 (2)0.1530 (2)0.4193 (2)0.0587 (7)
C90.0300 (2)0.1028 (2)0.3449 (2)0.0661 (8)
H(1)0.18220.06070.44980.0577*
H(2)0.09110.14460.32340.0631*
H(3)0.08530.14360.31850.0781*
H(4)0.00410.22760.44470.0701*
H(5)0.43580.21140.368520.0543*
H(6)0.42930.08870.418860.0542*
H(7)0.32320.01710.303290.0521*
H(8)0.41820.05800.260700.0524*
H(9)0.18750.26900.234970.0475*
H(10)0.17870.14540.283590.0474*
H(11)0.19310.29100.394660.0497*
H(12)0.28650.34120.354140.0496*
H(13)0.39940.01810.03440.0730*
H(14)0.24030.01920.09160.0676*
H(15)0.11070.03400.00680.0621*
H(16)0.13790.11980.137820.0512*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0422 (3)0.0651 (4)0.0428 (3)0.0047 (3)0.0054 (2)0.0109 (3)
Cl10.0669 (4)0.0597 (4)0.0883 (5)0.0105 (3)0.0157 (4)0.0288 (4)
Cl20.1055 (6)0.0631 (4)0.1085 (6)0.0040 (4)0.0250 (5)0.0319 (4)
Cl30.1237 (6)0.0659 (4)0.0417 (3)0.0014 (4)0.0077 (4)0.0070 (3)
Cl40.0971 (6)0.0958 (6)0.0783 (5)0.0231 (5)0.0405 (4)0.0006 (4)
O20.0569 (10)0.0575 (10)0.0597 (10)0.0178 (8)0.0070 (8)0.0050 (8)
F10.0457 (7)0.120 (1)0.0593 (9)0.0070 (8)0.0108 (6)0.0086 (9)
N30.0394 (8)0.0455 (10)0.0330 (8)0.0009 (8)0.0010 (7)0.0009 (7)
N20.0379 (8)0.0449 (10)0.0380 (9)0.0008 (7)0.0007 (7)0.0021 (7)
N10.0438 (10)0.0502 (11)0.0442 (10)0.0082 (8)0.0065 (8)0.0013 (8)
O10.0512 (9)0.0842 (13)0.0689 (11)0.0104 (9)0.0184 (8)0.0137 (10)
C120.0408 (11)0.0543 (13)0.0355 (10)0.0084 (10)0.0022 (8)0.0020 (9)
C130.0403 (10)0.0399 (11)0.0388 (10)0.0038 (9)0.0010 (8)0.0020 (9)
C150.0476 (11)0.0402 (11)0.0314 (10)0.0019 (9)0.0002 (8)0.0031 (8)
C30.0418 (10)0.0419 (11)0.0355 (10)0.0060 (9)0.0006 (8)0.0013 (9)
C50.0372 (10)0.0469 (12)0.0444 (11)0.0039 (9)0.0001 (9)0.0003 (9)
C40.0413 (10)0.0398 (11)0.0370 (10)0.0034 (9)0.0017 (8)0.0047 (8)
C110.0366 (10)0.059 (1)0.0398 (10)0.0004 (10)0.0036 (8)0.0017 (10)
C200.0440 (11)0.0501 (12)0.0342 (10)0.0054 (10)0.0018 (8)0.0024 (9)
C60.0428 (12)0.0523 (13)0.0491 (12)0.0022 (10)0.0049 (9)0.0008 (10)
C140.0483 (12)0.0357 (11)0.0403 (11)0.0006 (9)0.0010 (9)0.0019 (9)
C80.0511 (13)0.059 (2)0.0527 (13)0.0116 (12)0.0132 (10)0.0035 (12)
C10.0456 (12)0.0499 (13)0.058 (1)0.0012 (10)0.0042 (10)0.0004 (11)
C20.0521 (13)0.0459 (12)0.0416 (11)0.0029 (10)0.0037 (9)0.0041 (10)
C70.0537 (13)0.0465 (13)0.057 (1)0.0033 (11)0.0011 (11)0.0072 (11)
C160.0423 (12)0.069 (2)0.0398 (11)0.0008 (11)0.0067 (9)0.0033 (11)
C190.057 (1)0.058 (1)0.0398 (11)0.0051 (11)0.0068 (10)0.0005 (10)
C180.067 (2)0.066 (2)0.0360 (11)0.0103 (13)0.0021 (10)0.0049 (11)
C170.062 (2)0.080 (2)0.0410 (12)0.0128 (13)0.0118 (11)0.0024 (12)
C100.0457 (12)0.052 (1)0.077 (2)0.0056 (11)0.0050 (11)0.0056 (12)
C90.051 (1)0.064 (2)0.081 (2)0.0039 (12)0.0203 (13)0.004 (1)
Geometric parameters (Å, º) top
S1—C51.781 (2)C3—C21.454 (3)
S1—C41.763 (2)C5—C61.370 (3)
Cl1—C11.696 (2)C5—C101.382 (3)
Cl2—C11.726 (3)C11—H(5)0.95
Cl3—C21.745 (2)C11—H(6)0.95
Cl4—C81.737 (2)C20—C191.403 (3)
O2—N11.237 (2)C20—H(16)0.95
F1—C161.358 (3)C6—C71.397 (3)
N3—C121.475 (3)C6—H(1)0.95
N3—C131.470 (3)C14—H(11)0.95
N3—C151.427 (2)C14—H(12)0.95
N2—C41.336 (3)C8—C71.371 (3)
N2—C111.461 (3)C8—C91.356 (4)
N2—C141.470 (3)C1—C21.314 (3)
N1—O11.243 (2)C7—H(2)0.95
N1—C31.424 (3)C16—C171.378 (3)
C12—C111.522 (3)C19—C181.365 (3)
C12—H(7)0.95C19—H(15)0.95
C12—H(8)0.95C18—C171.383 (3)
C13—C141.520 (3)C18—H(14)0.95
C13—H(9)0.95C17—H(13)0.95
C13—H(10)0.95C10—C91.397 (4)
C15—C201.393 (3)C10—H(4)0.95
C15—C161.390 (3)C9—H(3)0.950 (4)
C3—C41.387 (3)
S1···N22.707 (2)C7···H(1)2.043 (3)
S1···C32.660 (2)C7···H(3)3.236 (3)
S1···C62.748 (2)C7···H(10)2.933 (3)
S1···C143.207 (2)C16···N32.440 (3)
S1···C23.072 (2)C16···C123.010 (3)
S1···C102.735 (2)C16···C202.365 (3)
S1···H(1)2.839 (2)C16···C192.739 (3)
S1···H(4)2.824 (2)C16···C182.383 (3)
S1···H(11)2.724 (2)C16···H(2)3.277 (3)
Cl1···Cl22.880 (1)C16···H(4)3.565 (3)
Cl1···C33.070 (2)C16···H(7)3.369 (3)
Cl1···C43.440 (2)C16···H(8)2.671 (3)
Cl1···C22.644 (2)C16···H(11)3.409 (3)
Cl1···H(1)2.777 (2)C16···H(12)3.566 (3)
Cl1···H(6)3.402 (2)C16···H(13)2.032 (3)
Cl2···Cl12.880 (1)C16···H(14)3.245 (3)
Cl2···Cl33.058 (1)C16···H(16)3.230 (3)
Cl2···Cl43.594 (1)C19···S12.473 (2)
Cl2···C22.679 (2)C19···Cl12.473 (2)
Cl3···Cl23.058 (1)C19···Cl22.473 (3)
Cl3···N13.236 (2)C19···Cl32.473 (2)
Cl3···O13.141 (2)C19···Cl42.473 (2)
Cl3···C32.740 (2)C19···O23.535 (3)
Cl3···C12.623 (2)C19···O23.414 (3)
Cl3···C93.565 (3)C19···O22.473 (3)
Cl3···H(3)2.780 (3)C19···F12.473 (3)
Cl4···S13.383 (1)C19···N32.473 (3)
Cl4···Cl13.383 (1)C19···N22.473 (3)
Cl4···Cl23.594 (1)C19···N12.473 (3)
Cl4···Cl23.383 (1)C19···O12.473 (3)
Cl4···Cl33.383 (1)C19···C122.473 (3)
Cl4···Cl43.383 (1)C19···C132.473 (3)
Cl4···O23.383 (2)C19···C152.437 (3)
Cl4···F13.383 (2)C19···C152.473 (3)
Cl4···N33.383 (2)C19···C32.473 (3)
Cl4···N23.383 (2)C19···C52.473 (3)
Cl4···N13.383 (2)C19···C42.473 (3)
Cl4···O13.383 (2)C19···C112.473 (3)
Cl4···C123.383 (2)C19···C202.473 (3)
Cl4···C133.383 (2)C19···C62.473 (3)
Cl4···C153.383 (2)C19···C142.473 (3)
Cl4···C33.383 (2)C19···C82.473 (3)
Cl4···C53.383 (2)C19···C12.473 (3)
Cl4···C43.383 (2)C19···C22.473 (3)
Cl4···C113.383 (2)C19···C72.473 (3)
Cl4···C203.383 (2)C19···C162.739 (3)
Cl4···C63.383 (2)C19···C162.473 (3)
Cl4···C143.383 (2)C19···C192.473 (3)
Cl4···C83.383 (2)C19···C182.473 (3)
Cl4···C13.383 (2)C19···C172.379 (3)
Cl4···C23.383 (2)C19···C172.473 (3)
Cl4···C72.680 (2)C19···C102.473 (3)
Cl4···C73.383 (2)C19···C92.473 (3)
Cl4···C163.383 (2)C19···H(1)2.473 (3)
Cl4···C193.383 (2)C19···H(2)2.473 (3)
Cl4···C183.383 (2)C19···H(3)2.473 (3)
Cl4···C173.383 (2)C19···H(4)2.473 (3)
Cl4···C103.383 (3)C19···H(5)2.473 (3)
Cl4···C92.678 (3)C19···H(6)2.473 (3)
Cl4···C93.383 (3)C19···H(7)2.473 (3)
Cl4···H(1)3.383 (2)C19···H(8)2.473 (3)
Cl4···H(2)2.768 (2)C19···H(9)2.473 (3)
Cl4···H(2)3.383 (2)C19···H(10)2.473 (3)
Cl4···H(3)2.772 (3)C19···H(11)3.573 (3)
Cl4···H(3)3.383 (3)C19···H(11)2.473 (3)
Cl4···H(4)3.383 (3)C19···H(12)2.996 (3)
Cl4···H(5)3.339 (2)C19···H(12)2.473 (3)
Cl4···H(5)3.383 (2)C19···H(13)3.237 (3)
Cl4···H(6)3.383 (2)C19···H(13)2.473 (3)
Cl4···H(7)3.383 (2)C19···H(14)2.013 (3)
Cl4···H(8)3.383 (2)C19···H(14)2.473 (3)
Cl4···H(9)3.383 (2)C19···H(15)2.473 (3)
Cl4···H(10)3.383 (2)C19···H(16)2.043 (3)
Cl4···H(11)3.383 (2)C19···H(16)2.473 (3)
Cl4···H(12)3.383 (2)C18···S13.540 (3)
Cl4···H(13)3.383 (2)C18···Cl13.540 (3)
Cl4···H(14)3.063 (2)C18···Cl23.540 (3)
Cl4···H(14)3.383 (2)C18···Cl33.599 (2)
Cl4···H(15)3.085 (2)C18···Cl33.540 (3)
Cl4···H(15)3.383 (2)C18···Cl43.540 (3)
Cl4···H(16)3.383 (2)C18···O23.540 (3)
O2···N22.823 (2)C18···F13.540 (3)
O2···O12.164 (2)C18···N33.540 (3)
O2···C32.307 (3)C18···N23.540 (3)
O2···C42.774 (2)C18···N13.540 (3)
O2···C112.818 (3)C18···O13.540 (3)
O2···C203.467 (3)C18···C123.540 (3)
O2···C23.545 (3)C18···C133.540 (3)
O2···C193.535 (3)C18···C152.811 (3)
O2···C193.414 (3)C18···C153.540 (3)
O2···H(5)2.506 (3)C18···C33.540 (3)
O2···H(6)2.751 (3)C18···C53.540 (3)
O2···H(12)3.523 (2)C18···C43.540 (3)
O2···H(15)2.951 (3)C18···C113.540 (3)
O2···H(15)2.865 (3)C18···C202.399 (3)
O2···H(16)2.958 (3)C18···C203.540 (3)
F1···N32.761 (2)C18···C63.540 (3)
F1···C122.937 (2)C18···C143.540 (3)
F1···C152.367 (3)C18···C83.540 (3)
F1···C73.584 (3)C18···C13.540 (3)
F1···C172.347 (3)C18···C23.540 (3)
F1···H(2)2.888 (3)C18···C73.540 (3)
F1···H(4)3.174 (3)C18···C162.383 (3)
F1···H(7)3.541 (3)C18···C163.540 (3)
F1···H(8)2.295 (2)C18···C193.540 (3)
F1···H(13)2.531 (3)C18···C183.540 (4)
F1···H(13)2.823 (3)C18···C173.540 (4)
N3···F12.761 (2)C18···C103.540 (3)
N3···N22.866 (2)C18···C93.540 (4)
N3···C112.480 (2)C18···H(1)3.540 (3)
N3···C202.486 (2)C18···H(2)3.540 (3)
N3···C142.453 (3)C18···H(3)3.540 (4)
N3···C73.558 (3)C18···H(4)3.540 (3)
N3···C162.440 (3)C18···H(5)3.540 (3)
N3···H(2)2.647 (3)C18···H(6)3.540 (3)
N3···H(5)2.675 (2)C18···H(7)3.540 (3)
N3···H(6)3.292 (2)C18···H(8)3.540 (3)
N3···H(7)1.998 (3)C18···H(9)3.540 (3)
N3···H(8)1.994 (3)C18···H(10)3.540 (3)
N3···H(9)1.993 (3)C18···H(11)3.286 (3)
N3···H(10)1.994 (3)C18···H(11)3.540 (3)
N3···H(11)3.262 (3)C18···H(12)3.340 (3)
N3···H(12)2.677 (3)C18···H(12)3.540 (3)
N3···H(16)2.676 (2)C18···H(13)2.034 (4)
N2···S12.707 (2)C18···H(13)3.540 (4)
N2···O22.823 (2)C18···H(14)3.540 (4)
N2···N32.866 (2)C18···H(15)2.017 (3)
N2···N12.958 (2)C18···H(15)3.540 (3)
N2···C122.423 (3)C18···H(16)3.248 (3)
N2···C132.473 (2)C18···H(16)3.540 (3)
N2···C32.407 (2)C17···F12.347 (3)
N2···C53.068 (3)C17···C152.432 (3)
N2···C63.373 (3)C17···C202.760 (3)
N2···H(1)3.288 (3)C17···C192.379 (3)
N2···H(5)1.992 (3)C17···H(4)3.507 (4)
N2···H(6)1.997 (3)C17···H(11)3.209 (3)
N2···H(7)2.606 (3)C17···H(13)3.574 (3)
N2···H(8)3.243 (3)C17···H(14)2.036 (3)
N2···H(9)3.283 (2)C17···H(15)3.239 (3)
N2···H(10)2.694 (2)C10···S12.735 (2)
N2···H(11)1.987 (3)C10···C62.382 (3)
N2···H(12)1.999 (3)C10···C143.520 (3)
N1···Cl33.236 (2)C10···C82.381 (3)
N1···N22.958 (2)C10···C72.773 (3)
N1···C42.447 (3)C10···H(1)3.238 (3)
N1···C113.027 (3)C10···H(3)2.048 (3)
N1···C13.437 (3)C10···H(10)3.011 (3)
N1···C22.413 (3)C10···H(11)2.837 (3)
N1···H(5)3.069 (3)C9···Cl33.565 (3)
N1···H(6)2.629 (3)C9···Cl42.678 (3)
N1···H(16)3.294 (3)C9···C52.398 (3)
O1···Cl33.141 (2)C9···C62.751 (3)
O1···O22.164 (2)C9···C72.384 (4)
O1···C32.292 (3)C9···H(2)3.232 (4)
O1···C43.553 (2)C9···H(4)2.050 (4)
O1···C203.571 (3)C9···H(10)3.099 (3)
O1···C13.489 (3)H(1)···S12.839 (2)
O1···C22.630 (3)H(1)···Cl12.777 (2)
O1···H(6)3.396 (3)H(1)···N23.288 (3)
O1···H(9)2.769 (3)H(1)···C52.015 (3)
O1···H(16)2.896 (3)H(1)···C43.014 (3)
C12···F12.937 (2)H(1)···C83.237 (3)
C12···N22.423 (3)H(1)···C72.043 (3)
C12···C132.415 (3)H(1)···C103.238 (3)
C12···C152.416 (3)H(2)···Cl42.768 (2)
C12···C43.539 (3)H(2)···F12.888 (3)
C12···C203.516 (3)H(2)···N32.647 (3)
C12···C142.831 (3)H(2)···C123.507 (3)
C12···C163.010 (3)H(2)···C133.425 (3)
C12···H(2)3.507 (3)H(2)···C153.150 (3)
C12···H(5)2.041 (3)H(2)···C53.269 (3)
C12···H(6)2.051 (3)H(2)···C62.063 (3)
C12···H(9)3.231 (3)H(2)···C82.019 (3)
C12···H(9)3.577 (3)H(2)···C163.277 (3)
C12···H(10)2.621 (3)H(2)···C93.232 (4)
C12···H(12)3.186 (3)H(3)···Cl32.780 (3)
C13···N22.473 (2)H(3)···Cl42.772 (3)
C13···C122.415 (3)H(3)···C53.258 (3)
C13···C152.426 (3)H(3)···C82.007 (4)
C13···C53.459 (3)H(3)···C73.236 (3)
C13···C112.889 (3)H(3)···C102.048 (3)
C13···C202.802 (3)H(4)···S12.824 (2)
C13···H(2)3.425 (3)H(4)···F13.174 (3)
C13···H(5)3.206 (3)H(4)···C52.032 (3)
C13···H(7)2.600 (3)H(4)···C63.240 (3)
C13···H(8)3.229 (3)H(4)···C83.239 (3)
C13···H(11)2.037 (3)H(4)···C163.565 (3)
C13···H(12)2.038 (3)H(4)···C173.507 (4)
C13···H(16)2.462 (3)H(4)···C92.050 (4)
C15···F12.367 (3)H(5)···Cl43.339 (2)
C15···C122.416 (3)H(5)···O22.506 (3)
C15···C132.426 (3)H(5)···N32.675 (2)
C15···C192.437 (3)H(5)···N21.992 (3)
C15···C182.811 (3)H(5)···N13.069 (3)
C15···C172.432 (3)H(5)···C122.041 (3)
C15···H(2)3.150 (3)H(5)···C133.206 (3)
C15···H(7)2.662 (3)H(5)···C33.371 (3)
C15···H(8)2.553 (3)H(5)···C43.005 (3)
C15···H(9)2.595 (3)H(5)···C142.639 (3)
C15···H(10)2.650 (3)H(6)···Cl13.402 (2)
C15···H(12)3.229 (3)H(6)···O22.751 (3)
C15···H(13)3.284 (3)H(6)···N33.292 (2)
C15···H(15)3.288 (3)H(6)···N21.997 (3)
C15···H(16)2.036 (3)H(6)···N12.629 (3)
C3···S12.660 (2)H(6)···O13.396 (3)
C3···Cl13.070 (2)H(6)···C122.051 (3)
C3···Cl32.740 (2)H(6)···C32.598 (3)
C3···O22.307 (3)H(6)···C42.520 (3)
C3···N22.407 (2)H(6)···C143.248 (3)
C3···O12.292 (3)H(7)···F13.541 (3)
C3···C112.948 (3)H(7)···N31.998 (3)
C3···C12.458 (3)H(7)···N22.606 (3)
C3···H(5)3.371 (3)H(7)···C132.600 (3)
C3···H(6)2.598 (3)H(7)···C152.662 (3)
C5···N23.068 (3)H(7)···C43.497 (3)
C5···C133.459 (3)H(7)···C112.032 (3)
C5···C42.785 (3)H(7)···C203.475 (3)
C5···C143.162 (3)H(7)···C63.316 (3)
C5···C82.746 (3)H(7)···C143.127 (3)
C5···C72.404 (3)H(7)···C163.369 (3)
C5···C92.398 (3)H(8)···F12.295 (2)
C5···H(1)2.015 (3)H(8)···N31.994 (3)
C5···H(2)3.269 (3)H(8)···N23.243 (3)
C5···H(3)3.258 (3)H(8)···C133.229 (3)
C5···H(4)2.032 (3)H(8)···C152.553 (3)
C5···H(10)2.846 (3)H(8)···C112.047 (3)
C5···H(11)2.693 (3)H(8)···C162.671 (3)
C4···Cl13.440 (2)H(9)···N31.993 (3)
C4···O22.774 (2)H(9)···N23.283 (2)
C4···N12.447 (3)H(9)···O12.769 (3)
C4···O13.553 (2)H(9)···C123.231 (3)
C4···C123.539 (3)H(9)···C123.577 (3)
C4···C52.785 (3)H(9)···C152.595 (3)
C4···C112.452 (3)H(9)···C202.701 (3)
C4···C63.240 (3)H(9)···C142.048 (3)
C4···C142.493 (3)H(10)···N31.994 (3)
C4···C13.257 (3)H(10)···N22.694 (2)
C4···C22.520 (3)H(10)···C122.621 (3)
C4···H(1)3.014 (3)H(10)···C152.650 (3)
C4···H(5)3.005 (3)H(10)···C52.846 (3)
C4···H(6)2.520 (3)H(10)···C113.227 (3)
C4···H(7)3.497 (3)H(10)···C202.709 (3)
C4···H(11)2.556 (3)H(10)···C62.846 (3)
C4···H(12)3.029 (3)H(10)···C142.041 (3)
C11···O22.818 (3)H(10)···C83.041 (3)
C11···N32.480 (2)H(10)···C72.933 (3)
C11···N13.027 (3)H(10)···C103.011 (3)
C11···C132.889 (3)H(10)···C93.099 (3)
C11···C32.948 (3)H(11)···S12.724 (2)
C11···C42.452 (3)H(11)···N33.262 (3)
C11···C142.430 (3)H(11)···N21.987 (3)
C11···H(7)2.032 (3)H(11)···C132.037 (3)
C11···H(8)2.047 (3)H(11)···C52.693 (3)
C11···H(10)3.227 (3)H(11)···C42.556 (3)
C11···H(11)3.233 (3)H(11)···C113.233 (3)
C11···H(12)2.652 (3)H(11)···C63.568 (3)
C20···S13.170 (2)H(11)···C163.409 (3)
C20···Cl13.170 (2)H(11)···C193.573 (3)
C20···Cl23.170 (2)H(11)···C183.286 (3)
C20···Cl33.170 (2)H(11)···C173.209 (3)
C20···Cl43.170 (2)H(11)···C102.837 (3)
C20···O23.467 (3)H(12)···O23.523 (2)
C20···O23.170 (3)H(12)···N32.677 (3)
C20···F13.170 (2)H(12)···N21.999 (3)
C20···N32.486 (2)H(12)···C123.186 (3)
C20···N33.170 (3)H(12)···C132.038 (3)
C20···N23.170 (3)H(12)···C153.229 (3)
C20···N13.170 (3)H(12)···C43.029 (3)
C20···O13.571 (3)H(12)···C112.652 (3)
C20···O13.170 (3)H(12)···C202.924 (3)
C20···C123.516 (3)H(12)···C163.566 (3)
C20···C123.170 (3)H(12)···C192.996 (3)
C20···C132.802 (3)H(12)···C183.340 (3)
C20···C133.170 (3)H(13)···Cl33.240 (2)
C20···C153.170 (3)H(13)···F12.531 (3)
C20···C33.170 (3)H(13)···F12.823 (3)
C20···C53.170 (3)H(13)···C153.284 (3)
C20···C43.170 (3)H(13)···C162.032 (3)
C20···C113.170 (3)H(13)···C193.237 (3)
C20···C203.170 (3)H(13)···C182.034 (4)
C20···C63.170 (3)H(13)···C173.574 (3)
C20···C143.170 (3)H(14)···Cl23.075 (3)
C20···C83.170 (3)H(14)···Cl33.173 (3)
C20···C13.170 (3)H(14)···Cl43.063 (2)
C20···C23.170 (3)H(14)···C203.257 (3)
C20···C73.170 (3)H(14)···C163.245 (3)
C20···C162.365 (3)H(14)···C192.013 (3)
C20···C163.170 (3)H(14)···C172.036 (3)
C20···C193.170 (3)H(15)···S11.581 (2)
C20···C182.399 (3)H(15)···Cl11.581 (2)
C20···C183.170 (3)H(15)···Cl21.581 (3)
C20···C172.760 (3)H(15)···Cl31.581 (2)
C20···C173.170 (3)H(15)···Cl43.085 (2)
C20···C103.170 (3)H(15)···Cl41.581 (2)
C20···C93.170 (3)H(15)···O22.951 (3)
C20···H(1)3.170 (3)H(15)···O22.865 (3)
C20···H(2)3.170 (3)H(15)···O21.581 (3)
C20···H(3)3.170 (3)H(15)···F11.581 (3)
C20···H(4)3.170 (3)H(15)···N31.581 (3)
C20···H(5)3.170 (3)H(15)···N21.581 (3)
C20···H(6)3.170 (3)H(15)···N11.581 (3)
C20···H(7)3.475 (3)H(15)···O11.581 (3)
C20···H(7)3.170 (3)H(15)···C121.581 (3)
C20···H(8)3.170 (3)H(15)···C131.581 (3)
C20···H(9)2.701 (3)H(15)···C153.288 (3)
C20···H(9)3.170 (3)H(15)···C151.581 (3)
C20···H(10)2.709 (3)H(15)···C31.581 (3)
C20···H(10)3.170 (3)H(15)···C51.581 (3)
C20···H(11)3.170 (3)H(15)···C41.581 (3)
C20···H(12)2.924 (3)H(15)···C111.581 (3)
C20···H(12)3.170 (3)H(15)···C202.048 (3)
C20···H(13)3.170 (3)H(15)···C201.581 (3)
C20···H(14)3.257 (3)H(15)···C61.581 (3)
C20···H(14)3.170 (3)H(15)···C141.581 (3)
C20···H(15)2.048 (3)H(15)···C81.581 (3)
C20···H(15)3.170 (3)H(15)···C11.581 (3)
C20···H(16)3.170 (3)H(15)···C21.581 (3)
C6···S12.748 (2)H(15)···C71.581 (3)
C6···N23.373 (3)H(15)···C161.581 (3)
C6···C43.240 (3)H(15)···C191.581 (3)
C6···C82.377 (3)H(15)···C182.017 (3)
C6···C102.382 (3)H(15)···C181.581 (3)
C6···C92.751 (3)H(15)···C173.239 (3)
C6···H(2)2.063 (3)H(15)···C171.581 (3)
C6···H(4)3.240 (3)H(15)···C101.581 (3)
C6···H(7)3.316 (3)H(15)···C91.581 (3)
C6···H(10)2.846 (3)H(16)···S13.006 (2)
C6···H(11)3.568 (3)H(16)···Cl13.006 (2)
C14···S13.207 (2)H(16)···Cl23.006 (2)
C14···N32.453 (3)H(16)···Cl33.006 (2)
C14···C122.831 (3)H(16)···Cl43.006 (2)
C14···C53.162 (3)H(16)···O22.958 (3)
C14···C42.493 (3)H(16)···O23.006 (3)
C14···C112.430 (3)H(16)···F13.006 (2)
C14···C103.520 (3)H(16)···N32.676 (2)
C14···H(5)2.639 (3)H(16)···N33.006 (3)
C14···H(6)3.248 (3)H(16)···N23.006 (3)
C14···H(7)3.127 (3)H(16)···N13.294 (3)
C14···H(9)2.048 (3)H(16)···N13.006 (3)
C14···H(10)2.041 (3)H(16)···O12.896 (3)
C8···C52.746 (3)H(16)···O13.006 (3)
C8···C62.377 (3)H(16)···C123.006 (3)
C8···C102.381 (3)H(16)···C132.462 (3)
C8···H(1)3.237 (3)H(16)···C133.006 (3)
C8···H(2)2.019 (3)H(16)···C152.036 (3)
C8···H(3)2.007 (4)H(16)···C153.006 (3)
C8···H(4)3.239 (3)H(16)···C33.006 (3)
C8···H(10)3.041 (3)H(16)···C53.006 (3)
C8···H(16)3.552 (3)H(16)···C43.006 (3)
C1···Cl32.623 (2)H(16)···C113.006 (3)
C1···N13.437 (3)H(16)···C203.006 (3)
C1···O13.489 (3)H(16)···C63.006 (3)
C1···C32.458 (3)H(16)···C143.006 (3)
C1···C43.257 (3)H(16)···C83.552 (3)
C2···S13.072 (2)H(16)···C83.006 (3)
C2···Cl12.644 (2)H(16)···C13.006 (3)
C2···Cl22.679 (2)H(16)···C23.006 (3)
C2···O23.545 (3)H(16)···C73.006 (3)
C2···N12.413 (3)H(16)···C163.230 (3)
C2···O12.630 (3)H(16)···C163.006 (3)
C2···C42.520 (3)H(16)···C192.043 (3)
C7···Cl42.680 (2)H(16)···C193.006 (3)
C7···F13.584 (3)H(16)···C183.248 (3)
C7···N33.558 (3)H(16)···C183.006 (3)
C7···C52.404 (3)H(16)···C173.006 (3)
C7···C102.773 (3)H(16)···C103.006 (3)
C7···C92.384 (4)H(16)···C93.006 (3)
C5—S1—C4103.58 (9)C19—C20—C15121.3 (2)
C12—N3—C13110.2 (2)H(16)—C20—C15119.5 (2)
C12—N3—C15112.8 (2)C7—C6—H(1)119.8 (3)
C13—N3—C15113.8 (1)C7—C6—C5120.6 (2)
C4—N2—C11122.4 (2)H(1)—C6—C5119.5 (2)
C4—N2—C14125.3 (2)H(11)—C14—H(12)109.5 (3)
C11—N2—C14112.0 (2)H(11)—C14—N2108.5 (2)
O1—N1—C3118.3 (2)H(11)—C14—C13108.9 (2)
O1—N1—O2121.5 (2)H(12)—C14—N2109.5 (2)
C3—N1—O2120.1 (2)H(12)—C14—C13109.0 (2)
C11—C12—H(7)108.3 (2)N2—C14—C13111.5 (2)
C11—C12—H(8)109.6 (2)C7—C8—C9121.9 (2)
C11—C12—N3111.7 (2)C7—C8—Cl4118.7 (2)
H(7)—C12—H(8)109.5 (3)C9—C8—Cl4119.4 (2)
H(7)—C12—N3109.0 (2)C2—C1—Cl1122.4 (2)
H(8)—C12—N3108.7 (2)C2—C1—Cl2123.0 (2)
C14—C13—H(9)109.8 (2)Cl1—C1—Cl2114.6 (1)
C14—C13—H(10)109.2 (2)Cl3—C2—C3117.5 (2)
C14—C13—N3110.3 (2)Cl3—C2—C1117.3 (2)
H(9)—C13—H(10)109.5 (2)C3—C2—C1125.2 (2)
H(9)—C13—N3109.0 (2)H(2)—C7—C6121.9 (3)
H(10)—C13—N3109.1 (2)H(2)—C7—C8119.7 (3)
C20—C15—C16116.3 (2)C6—C7—C8118.3 (2)
C20—C15—N3123.6 (2)C17—C16—F1118.2 (2)
C16—C15—N3120.0 (2)C17—C16—C15122.9 (2)
C4—C3—C2124.9 (2)F1—C16—C15118.9 (2)
C4—C3—N1121.0 (2)C18—C19—H(15)120.1 (2)
C2—C3—N1113.9 (2)C18—C19—C20120.1 (2)
C6—C5—C10120.0 (2)H(15)—C19—C20119.7 (3)
C6—C5—S1120.8 (2)C17—C18—H(14)120.4 (3)
C10—C5—S1119.2 (2)C17—C18—C19119.9 (2)
S1—C4—N2121.1 (1)H(14)—C18—C19119.7 (3)
S1—C4—C3114.7 (1)H(13)—C17—C16120.5 (3)
N2—C4—C3124.2 (2)H(13)—C17—C18120.2 (3)
H(5)—C11—H(6)109.5 (3)C16—C17—C18119.3 (2)
H(5)—C11—N2109.6 (2)C9—C10—H(4)120.5 (3)
H(5)—C11—C12109.1 (2)C9—C10—C5119.3 (2)
H(6)—C11—N2110.1 (2)H(4)—C10—C5120.2 (3)
H(6)—C11—C12109.9 (2)H(3)—C9—C8119.9 (3)
N2—C11—C12108.6 (2)H(3)—C9—C10120.3 (3)
C19—C20—H(16)119.2 (2)C8—C9—C10119.7 (2)
C4—S1—C5—C656.7 (2)N3—C15—C20—H(16)1.4 (4)
C4—S1—C5—C10125.6 (2)C16—C15—C20—C192.5 (3)
C5—S1—C4—N237.5 (2)C16—C15—C20—H(16)177.2 (2)
C5—S1—C4—C3142.3 (1)N3—C15—C16—F12.5 (3)
C13—N3—C12—C1158.6 (2)N3—C15—C16—C17178.2 (2)
C13—N3—C12—H(7)61.0 (2)C20—C15—C16—F1176.1 (2)
C13—N3—C12—H(8)179.7 (2)C20—C15—C16—C173.1 (3)
C15—N3—C12—C11173.0 (2)N1—C3—C4—S1145.2 (2)
C15—N3—C12—H(7)67.3 (2)N1—C3—C4—N235.0 (3)
C15—N3—C12—H(8)52.0 (3)C2—C3—C4—S130.5 (3)
C12—N3—C13—C1455.9 (2)C2—C3—C4—N2149.3 (2)
C12—N3—C13—H(9)176.5 (2)N1—C3—C2—Cl365.4 (2)
C12—N3—C13—H(10)64.0 (2)N1—C3—C2—C1115.1 (2)
C15—N3—C13—C14176.3 (2)C4—C3—C2—Cl3110.5 (2)
C15—N3—C13—H(9)55.7 (3)C4—C3—C2—C169.0 (3)
C15—N3—C13—H(10)63.8 (2)S1—C5—C6—C7177.5 (2)
C12—N3—C15—C20118.4 (2)S1—C5—C6—H(1)0.4 (4)
C12—N3—C15—C1663.0 (2)C10—C5—C6—C74.8 (3)
C13—N3—C15—C208.0 (3)C10—C5—C6—H(1)177.3 (3)
C13—N3—C15—C16170.6 (2)S1—C5—C10—C9178.5 (2)
C11—N2—C4—S1153.8 (1)S1—C5—C10—H(4)1.7 (4)
C11—N2—C4—C326.0 (3)C6—C5—C10—C93.8 (3)
C14—N2—C4—S133.5 (3)C6—C5—C10—H(4)176.0 (3)
C14—N2—C4—C3146.8 (2)C15—C20—C19—C180.1 (3)
C4—N2—C11—C12129.8 (2)C15—C20—C19—H(15)179.5 (3)
C4—N2—C11—H(5)111.1 (2)H(16)—C20—C19—C18179.6 (3)
C4—N2—C11—H(6)9.4 (3)H(16)—C20—C19—H(15)0.8 (4)
C14—N2—C11—C1256.6 (2)C5—C6—C7—C82.7 (3)
C14—N2—C11—H(5)62.5 (2)C5—C6—C7—H(2)179.8 (3)
C14—N2—C11—H(6)177.0 (2)H(1)—C6—C7—C8179.4 (3)
C4—N2—C14—C13130.2 (2)H(1)—C6—C7—H(2)2.3 (4)
C4—N2—C14—H(11)10.3 (3)Cl4—C8—C7—C6177.2 (2)
C4—N2—C14—H(12)109.1 (2)Cl4—C8—C7—H(2)5.6 (4)
C11—N2—C14—C1356.4 (2)C9—C8—C7—C60.5 (4)
C11—N2—C14—H(11)176.3 (2)C9—C8—C7—H(2)176.7 (3)
C11—N2—C14—H(12)64.3 (2)Cl4—C8—C9—C10176.3 (2)
O2—N1—C3—C413.3 (3)Cl4—C8—C9—H(3)3.6 (4)
O2—N1—C3—C2162.9 (2)C7—C8—C9—C101.4 (4)
O1—N1—C3—C4170.1 (2)C7—C8—C9—H(3)178.7 (3)
O1—N1—C3—C213.8 (3)Cl1—C1—C2—Cl3177.7 (2)
N3—C12—C11—N258.1 (2)Cl1—C1—C2—C32.8 (3)
N3—C12—C11—H(5)61.3 (3)Cl2—C1—C2—Cl32.0 (3)
N3—C12—C11—H(6)178.7 (2)Cl2—C1—C2—C3177.5 (2)
H(7)—C12—C11—N262.0 (3)F1—C16—C17—C18177.9 (2)
H(7)—C12—C11—H(5)178.6 (3)F1—C16—C17—H(13)3.1 (4)
H(7)—C12—C11—H(6)58.6 (3)C15—C16—C17—C181.3 (4)
H(8)—C12—C11—N2178.7 (2)C15—C16—C17—H(13)177.7 (3)
H(8)—C12—C11—H(5)59.2 (3)C20—C19—C18—C171.9 (4)
H(8)—C12—C11—H(6)60.8 (3)C20—C19—C18—H(14)178.6 (3)
N3—C13—C14—N255.0 (2)H(15)—C19—C18—C17178.6 (3)
N3—C13—C14—H(11)174.7 (2)H(15)—C19—C18—H(14)0.9 (5)
N3—C13—C14—H(12)65.9 (3)C19—C18—C17—C161.3 (4)
H(9)—C13—C14—N2175.2 (2)C19—C18—C17—H(13)179.8 (3)
H(9)—C13—C14—H(11)65.1 (3)H(14)—C18—C17—C16179.2 (3)
H(9)—C13—C14—H(12)54.2 (3)H(14)—C18—C17—H(13)0.2 (5)
H(10)—C13—C14—N264.8 (3)C5—C10—C9—C80.8 (4)
H(10)—C13—C14—H(11)54.9 (3)C5—C10—C9—H(3)179.2 (3)
H(10)—C13—C14—H(12)174.2 (3)H(4)—C10—C9—C8179.1 (3)
N3—C15—C20—C19178.9 (2)H(4)—C10—C9—H(3)1.0 (5)
 

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