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The title compound, C19H13N3O2S2, is a macrocycle with a `wheelchair' conformation. The `backrest' pyridine ring is tilted by 142.87 (7)° with respect to the `seat' plane, and the two `wheel' pyridine rings are tilted by 70.33 (3)° with respect to one another.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806041262/is2084sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806041262/is2084IIsup2.hkl
Contains datablock II

CCDC reference: 627812

Key indicators

  • Single-crystal X-ray study
  • T = 110 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.043
  • wR factor = 0.108
  • Data-to-parameter ratio = 34.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

14,17-Dithia-22,23,24-triazatetracyclo[16.3.1.13,7.19,13]tetracosa- 1(22),3,5,7(24),9,11,13 (23),18,20-nonaene-2,8-dione top
Crystal data top
C19H13N3O2S2F(000) = 784
Mr = 379.44Dx = 1.433 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7195 reflections
a = 8.7102 (10) Åθ = 2.5–36.3°
b = 13.1725 (13) ŵ = 0.32 mm1
c = 15.497 (2) ÅT = 110 K
β = 98.532 (5)°Plate, colorless
V = 1758.4 (3) Å30.37 × 0.35 × 0.17 mm
Z = 4
Data collection top
Nonius KappaCCD (with Oxford Cryostream)
diffractometer
6267 reflections with I > 2σ(I)
ω scansRint = 0.026
Absorption correction: multi-scan
(SCALPACK; Otwinowski & Minor, 1997)
θmax = 36.4°, θmin = 2.8°
Tmin = 0.890, Tmax = 0.947h = 1414
35062 measured reflectionsk = 2121
8240 independent reflectionsl = 2525
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0415P)2 + 0.7446P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.043(Δ/σ)max = 0.001
wR(F2) = 0.108Δρmax = 0.47 e Å3
S = 1.03Δρmin = 0.42 e Å3
8240 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
236 parametersExtinction coefficient: 0.0054 (8)
0 restraints
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*/Ueq
S10.21648 (3)0.62831 (2)0.67641 (2)0.02468 (7)
S20.21641 (3)0.82946 (3)0.53572 (2)0.02601 (7)
O10.89183 (10)0.94448 (7)0.61725 (6)0.02800 (18)
O20.86296 (12)0.45176 (8)0.64058 (7)0.0376 (2)
N10.49854 (11)0.55833 (7)0.65806 (6)0.01900 (16)
N20.77167 (10)0.69644 (7)0.64052 (6)0.01817 (16)
N30.52520 (10)0.85003 (7)0.56563 (6)0.01743 (15)
C10.59496 (13)0.49126 (8)0.62823 (7)0.02020 (19)
C20.54483 (16)0.40508 (8)0.58044 (8)0.0259 (2)
H20.61680.35920.56130.031*
C30.38582 (17)0.38836 (9)0.56161 (8)0.0291 (3)
H30.3470.33010.52940.035*
C40.28454 (15)0.45740 (9)0.59017 (8)0.0261 (2)
H40.17540.44780.57750.031*
C50.34682 (13)0.54211 (8)0.63837 (7)0.02035 (19)
C60.33559 (13)0.74106 (8)0.69817 (7)0.02077 (19)
H6A0.35580.7530.76190.025*
H6B0.43670.72960.67790.025*
C70.25933 (13)0.83494 (9)0.65336 (7)0.02084 (19)
H7A0.32830.89380.66950.025*
H7B0.16120.84770.67660.025*
C80.39959 (12)0.85304 (8)0.50503 (7)0.01813 (17)
C90.40557 (14)0.87391 (8)0.41671 (7)0.02111 (19)
H90.31390.8730.3750.025*
C100.54815 (15)0.89584 (9)0.39176 (7)0.0232 (2)
H100.55620.90920.33240.028*
C110.67969 (14)0.89800 (8)0.45505 (7)0.02151 (19)
H110.77840.91560.44050.026*
C120.66168 (12)0.87359 (7)0.53986 (7)0.01741 (17)
C130.79831 (12)0.87499 (8)0.61091 (7)0.01911 (18)
C140.82082 (12)0.78724 (8)0.67325 (7)0.01817 (17)
C150.89879 (13)0.80147 (10)0.75742 (7)0.0228 (2)
H150.92810.86750.77830.027*
C160.93272 (13)0.71670 (11)0.81012 (7)0.0257 (2)
H160.98360.72370.86840.031*
C170.89082 (13)0.62143 (10)0.77591 (7)0.0231 (2)
H170.91710.56170.80920.028*
C180.80937 (12)0.61562 (8)0.69166 (7)0.01907 (18)
C190.76386 (14)0.51380 (8)0.65160 (7)0.0229 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01979 (12)0.02561 (13)0.02956 (15)0.00449 (9)0.00670 (10)0.00096 (10)
S20.01742 (12)0.03852 (16)0.02081 (13)0.00179 (10)0.00132 (9)0.00493 (11)
O10.0245 (4)0.0234 (4)0.0352 (5)0.0076 (3)0.0016 (3)0.0020 (3)
O20.0364 (5)0.0302 (5)0.0435 (6)0.0184 (4)0.0030 (4)0.0040 (4)
N10.0229 (4)0.0171 (4)0.0170 (4)0.0009 (3)0.0030 (3)0.0000 (3)
N20.0170 (4)0.0189 (4)0.0177 (4)0.0017 (3)0.0002 (3)0.0005 (3)
N30.0187 (4)0.0174 (4)0.0159 (4)0.0003 (3)0.0018 (3)0.0005 (3)
C10.0290 (5)0.0148 (4)0.0167 (4)0.0023 (4)0.0029 (4)0.0025 (3)
C20.0427 (7)0.0149 (4)0.0201 (5)0.0011 (4)0.0043 (4)0.0001 (4)
C30.0465 (7)0.0181 (5)0.0217 (5)0.0087 (5)0.0020 (5)0.0023 (4)
C40.0326 (6)0.0234 (5)0.0214 (5)0.0107 (4)0.0011 (4)0.0004 (4)
C50.0248 (5)0.0194 (4)0.0168 (4)0.0045 (4)0.0032 (4)0.0011 (3)
C60.0209 (4)0.0213 (5)0.0196 (5)0.0012 (4)0.0013 (4)0.0002 (4)
C70.0190 (4)0.0238 (5)0.0202 (5)0.0027 (4)0.0045 (4)0.0002 (4)
C80.0197 (4)0.0169 (4)0.0172 (4)0.0007 (3)0.0006 (3)0.0003 (3)
C90.0272 (5)0.0191 (4)0.0160 (4)0.0031 (4)0.0002 (4)0.0000 (3)
C100.0340 (6)0.0198 (4)0.0164 (4)0.0015 (4)0.0054 (4)0.0010 (3)
C110.0265 (5)0.0192 (4)0.0202 (5)0.0011 (4)0.0079 (4)0.0010 (4)
C120.0203 (4)0.0137 (4)0.0183 (4)0.0003 (3)0.0030 (3)0.0021 (3)
C130.0181 (4)0.0190 (4)0.0206 (5)0.0005 (3)0.0042 (3)0.0041 (3)
C140.0149 (4)0.0220 (4)0.0174 (4)0.0014 (3)0.0020 (3)0.0023 (3)
C150.0174 (4)0.0321 (5)0.0186 (5)0.0046 (4)0.0022 (3)0.0049 (4)
C160.0184 (5)0.0426 (7)0.0154 (4)0.0011 (4)0.0003 (3)0.0014 (4)
C170.0173 (4)0.0338 (6)0.0181 (5)0.0053 (4)0.0024 (3)0.0046 (4)
C180.0155 (4)0.0224 (4)0.0190 (4)0.0047 (3)0.0015 (3)0.0009 (3)
C190.0283 (5)0.0188 (4)0.0208 (5)0.0074 (4)0.0010 (4)0.0033 (4)
Geometric parameters (Å, º) top
C1—C191.4918 (17)C13—C141.5005 (16)
C1—C21.3899 (16)C14—C151.3910 (15)
C2—C31.390 (2)C15—C161.3891 (18)
C2—H20.95C15—H150.95
C3—C41.3846 (19)C16—C171.3897 (18)
C3—H30.95C16—H160.95
C4—C51.4060 (16)C17—C181.3926 (15)
C4—H40.95C17—H170.95
C6—C71.5218 (15)C18—C191.5060 (16)
C6—H6A0.99N1—C11.3471 (14)
C6—H6B0.99N1—C51.3288 (14)
C7—H7A0.99N2—C141.3440 (14)
C7—H7B0.99N2—C181.3387 (14)
C8—C91.4047 (15)N3—C121.3453 (14)
C9—C101.3847 (17)N3—C81.3326 (13)
C9—H90.95O1—C131.2196 (13)
C10—C111.3935 (17)O2—C191.2190 (14)
C10—H100.95S1—C51.7676 (12)
C11—C121.3845 (15)S1—C61.8144 (11)
C11—H110.95S2—C71.8073 (12)
C12—C131.4967 (15)S2—C81.7588 (11)
C2—C1—C19120.83 (10)C11—C10—H10120.5
N1—C1—C19115.38 (9)C9—C10—H10120.5
N1—C1—C2123.78 (11)C12—C11—C10117.79 (10)
C1—C2—C3117.76 (11)C10—C11—H11121.1
C1—C2—H2121.1C12—C11—H11121.1
C3—C2—H2121.1N3—C12—C11124.40 (10)
C4—C3—C2119.41 (11)C11—C12—C13120.39 (10)
C2—C3—H3120.3N3—C12—C13115.19 (9)
C4—C3—H3120.3O1—C13—C12121.14 (10)
C3—C4—C5118.50 (11)C12—C13—C14118.55 (9)
C3—C4—H4120.7O1—C13—C14120.29 (10)
C5—C4—H4120.7C15—C14—C13119.93 (10)
N1—C5—C4122.81 (11)N2—C14—C13116.02 (9)
C4—C5—S1118.08 (9)N2—C14—C15123.89 (10)
N1—C5—S1119.09 (8)C16—C15—C14118.34 (11)
C7—C6—H6A109.1C14—C15—H15120.8
S1—C6—H6A109.1C16—C15—H15120.8
C7—C6—H6B109.1C15—C16—C17118.73 (10)
H6A—C6—H6B107.9C15—C16—H16120.6
S1—C6—H6B109.1C17—C16—H16120.6
C7—C6—S1112.43 (8)C16—C17—C18118.41 (11)
C6—C7—H7A108.3C16—C17—H17120.8
S2—C7—H7A108.3C18—C17—H17120.8
C6—C7—H7B108.3N2—C18—C17123.87 (10)
H7A—C7—H7B107.4C17—C18—C19120.12 (10)
S2—C7—H7B108.3N2—C18—C19115.97 (9)
C6—C7—S2116.02 (8)O2—C19—C1121.73 (11)
N3—C8—C9123.18 (10)C1—C19—C18117.85 (9)
C9—C8—S2117.67 (8)O2—C19—C18120.41 (11)
N3—C8—S2119.15 (8)C5—N1—C1117.72 (10)
C10—C9—C8118.51 (10)C18—N2—C14116.61 (9)
C10—C9—H9120.7C8—N3—C12116.95 (9)
C8—C9—H9120.7C5—S1—C6102.12 (5)
C9—C10—C11119.05 (10)C8—S2—C7101.86 (5)
C2—C1—C19—O210.27 (18)C14—C15—C16—C171.53 (16)
C2—C1—C19—C18171.15 (10)C15—C16—C17—C183.28 (16)
N1—C1—C19—O2168.43 (11)C16—C17—C18—N21.55 (17)
N1—C1—C19—C1810.15 (14)C16—C17—C18—C19179.07 (10)
C19—C1—C2—C3179.47 (10)C17—C18—C19—O261.27 (16)
N1—C1—C2—C30.88 (17)C17—C18—C19—C1117.33 (11)
C1—C2—C3—C40.43 (17)N2—C18—C19—O2116.43 (13)
C2—C3—C4—C50.65 (17)N2—C18—C19—C164.97 (14)
C3—C4—C5—N10.41 (17)C5—N1—C1—C21.90 (16)
C3—C4—C5—S1178.71 (9)C5—N1—C1—C19179.44 (9)
S1—C6—C7—S260.06 (10)C1—N1—C5—C41.64 (16)
N3—C8—C9—C102.26 (16)C1—N1—C5—S1179.93 (8)
S2—C8—C9—C10177.98 (8)C18—N2—C14—C153.94 (16)
C8—C9—C10—C111.00 (16)C18—N2—C14—C13171.39 (9)
C9—C10—C11—C122.73 (16)C14—N2—C18—C172.00 (16)
C10—C11—C12—N31.48 (16)C14—N2—C18—C19175.61 (9)
C10—C11—C12—C13179.71 (10)C8—N3—C12—C111.61 (15)
C11—C12—C13—O144.36 (15)C8—N3—C12—C13176.70 (9)
C11—C12—C13—C14133.96 (10)C12—N3—C8—C93.51 (15)
N3—C12—C13—O1134.02 (11)C12—N3—C8—S2176.74 (7)
N3—C12—C13—C1447.66 (13)C6—S1—C5—N120.89 (10)
C12—C13—C14—N231.63 (13)C6—S1—C5—C4160.75 (9)
C12—C13—C14—C15152.84 (10)C5—S1—C6—C7127.35 (8)
O1—C13—C14—N2146.70 (11)C8—S2—C7—C678.49 (9)
O1—C13—C14—C1528.83 (15)C7—S2—C8—N312.27 (10)
C13—C14—C15—C16172.94 (10)C7—S2—C8—C9167.96 (8)
N2—C14—C15—C162.22 (17)
 

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