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In the title compound (systematic name: 1-chloro-4-propoxy-10-thia­anthracen-9-one), C16H13ClO2S, the asymmetric unit contains two parallel molecules. In both molecules, the three rings in the thio­xanthone moiety are coplanar, the deviations being within the range ±0.086 (3) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804031770/dn6184sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804031770/dn6184Isup2.hkl
Contains datablock I

CCDC reference: 262478

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.042
  • wR factor = 0.128
  • Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C31
Alert level C PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.93 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.16 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C30 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C31A PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 32.60 Deg. C30A -O4 -C30 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C16 H13 Cl O2 S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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 (Farrugia, 1999).

1-Chloro-4-propoxy-10-thiaanthracen-9-one top
Crystal data top
C16H13ClO2SZ = 4
Mr = 304.78F(000) = 632
Triclinic, P1Dx = 1.425 Mg m3
Hall symbol: -P 1Melting point: 372 K
a = 11.298 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.841 (2) ÅCell parameters from 25 reflections
c = 12.776 (3) Åθ = 11.7–13.3°
α = 108.28 (2)°µ = 0.41 mm1
β = 112.84 (2)°T = 293 K
γ = 98.71 (2)°Prism, yellow
V = 1420.9 (7) Å30.35 × 0.25 × 0.15 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
3225 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 25.2°, θmin = 1.9°
ω/2θ scansh = 113
Absorption correction: empirical (using intensity measurements)
(Blessing, 1995)
k = 1414
Tmin = 0.878, Tmax = 0.934l = 1514
5950 measured reflections3 standard reflections every 60 min
5106 independent reflections intensity decay: 0.3%
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0519P)2 + 0.769P]
where P = (Fo2 + 2Fc2)/3
5106 reflections(Δ/σ)max = 0.016
391 parametersΔρmax = 0.51 e Å3
47 restraintsΔρmin = 0.48 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)
C11.1549 (3)0.3781 (3)0.2576 (3)0.0699 (8)
C21.1417 (4)0.2640 (3)0.1773 (3)0.0796 (9)
H21.19960.22020.20560.096*
C31.0436 (3)0.2122 (3)0.0543 (3)0.0727 (8)
H31.03690.13510.00030.087*
C40.9568 (3)0.2754 (3)0.0139 (3)0.0583 (7)
C50.8030 (3)0.6735 (3)0.1166 (3)0.0665 (8)
H50.73720.64830.03500.080*
C60.8198 (3)0.7832 (3)0.2062 (3)0.0770 (9)
H60.76670.83320.18520.092*
C70.9156 (3)0.8203 (3)0.3285 (3)0.0752 (9)
H70.92430.89320.39030.090*
C80.9969 (3)0.7496 (3)0.3577 (3)0.0648 (8)
H81.06240.77620.43970.078*
C91.0826 (3)0.5718 (3)0.3074 (3)0.0657 (8)
C101.0693 (3)0.4481 (2)0.2205 (2)0.0532 (6)
C110.9682 (3)0.3933 (2)0.0957 (2)0.0496 (6)
C120.8844 (3)0.5985 (2)0.1465 (2)0.0520 (6)
C130.9850 (3)0.6380 (2)0.2679 (2)0.0530 (6)
C140.8400 (3)0.1175 (3)0.1948 (3)0.0681 (8)
H14A0.82400.05050.16880.082*
H14B0.92170.12220.20390.082*
C150.7224 (3)0.0930 (3)0.3157 (3)0.0750 (9)
H15A0.73900.16110.34010.090*
H15B0.64160.08960.30520.090*
C160.7001 (4)0.0296 (3)0.4173 (3)0.0965 (12)
H16A0.77930.02550.42910.145*
H16B0.62400.04360.49360.145*
H16C0.68300.09710.39350.145*
C170.1429 (3)0.7924 (3)0.2513 (3)0.0709 (8)
C180.1190 (4)0.6804 (3)0.3383 (3)0.0824 (10)
H180.04790.65280.41800.099*
C190.1980 (4)0.6064 (3)0.3114 (3)0.0790 (10)
H190.17980.52890.37260.095*
C200.3039 (3)0.6459 (3)0.1943 (3)0.0653 (8)
C210.5835 (3)1.0010 (3)0.2545 (3)0.0724 (9)
H210.64020.95610.28240.087*
C220.6041 (4)1.1188 (4)0.3325 (3)0.0865 (11)
H220.67371.15360.41370.104*
C230.5218 (4)1.1869 (3)0.2916 (4)0.0888 (12)
H230.53681.26810.34470.107*
C240.4182 (4)1.1350 (3)0.1729 (3)0.0751 (9)
H240.36341.18170.14590.090*
C250.2727 (3)0.9604 (3)0.0314 (3)0.0653 (8)
C260.2488 (3)0.8386 (2)0.1277 (3)0.0562 (7)
C270.3287 (3)0.7623 (2)0.1011 (2)0.0533 (6)
C280.4784 (3)0.9465 (2)0.1328 (3)0.0555 (7)
C290.3929 (3)1.0129 (2)0.0912 (3)0.0577 (7)
Cl11.28208 (12)0.42744 (12)0.40866 (9)0.1218 (5)
Cl20.03971 (11)0.87766 (11)0.30434 (10)0.1082 (4)
O11.1754 (3)0.6216 (3)0.4122 (2)0.1313 (12)
O20.8545 (2)0.23424 (18)0.10402 (18)0.0697 (6)
O30.1927 (3)1.0189 (3)0.0505 (3)0.1148 (10)
S10.85021 (7)0.45935 (6)0.02566 (6)0.0548 (2)
S20.46336 (8)0.79614 (7)0.04245 (7)0.0630 (2)
O40.3926 (2)0.58496 (19)0.1560 (2)0.0848 (7)
C300.3816 (6)0.4791 (5)0.2619 (4)0.0616 (15)0.66
H30A0.38160.50470.32700.074*0.66
H30B0.29980.41050.29630.074*0.66
C310.5052 (7)0.4425 (5)0.2056 (6)0.0749 (16)0.66
H31A0.50270.41400.14290.090*0.66
H31B0.58630.51310.16710.090*0.66
C320.503 (3)0.3337 (16)0.3157 (19)0.156 (9)0.66
H32A0.41950.26720.35660.234*0.66
H32B0.57720.30270.28360.234*0.66
H32C0.51210.36480.37410.234*0.66
C30A0.4167 (16)0.4657 (9)0.1993 (14)0.083 (4)0.34
H30C0.33200.40050.26090.099*0.34
H30D0.45790.44250.13030.099*0.34
C31A0.5086 (13)0.4805 (10)0.2549 (12)0.081 (3)0.34
H31C0.59410.54510.19490.097*0.34
H31D0.46750.49910.32710.097*0.34
C32A0.526 (4)0.345 (3)0.292 (3)0.113 (10)0.34
H32D0.44450.28370.31420.170*0.34
H32E0.59990.34280.22330.170*0.34
H32F0.54440.32570.36230.170*0.34
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.074 (2)0.085 (2)0.0577 (17)0.0367 (17)0.0303 (15)0.0326 (17)
C20.090 (2)0.092 (2)0.078 (2)0.053 (2)0.044 (2)0.042 (2)
C30.087 (2)0.069 (2)0.073 (2)0.0361 (18)0.0473 (19)0.0244 (17)
C40.0619 (17)0.0612 (17)0.0530 (16)0.0166 (14)0.0314 (14)0.0200 (14)
C50.0616 (18)0.0579 (17)0.0632 (18)0.0167 (14)0.0171 (14)0.0203 (15)
C60.071 (2)0.0542 (18)0.093 (2)0.0223 (15)0.0304 (19)0.0231 (17)
C70.079 (2)0.0504 (17)0.077 (2)0.0156 (16)0.0333 (18)0.0090 (15)
C80.0673 (19)0.0525 (16)0.0543 (16)0.0086 (14)0.0216 (14)0.0104 (13)
C90.0684 (19)0.0608 (18)0.0481 (16)0.0178 (15)0.0139 (14)0.0162 (14)
C100.0537 (15)0.0595 (16)0.0483 (14)0.0173 (13)0.0241 (12)0.0239 (13)
C110.0541 (15)0.0496 (15)0.0498 (14)0.0150 (12)0.0294 (12)0.0199 (12)
C120.0496 (15)0.0475 (14)0.0525 (15)0.0092 (12)0.0219 (12)0.0179 (12)
C130.0549 (16)0.0462 (14)0.0489 (15)0.0070 (12)0.0221 (12)0.0151 (12)
C140.078 (2)0.0573 (17)0.0628 (18)0.0147 (15)0.0407 (16)0.0095 (14)
C150.076 (2)0.0650 (19)0.066 (2)0.0082 (16)0.0371 (17)0.0062 (15)
C160.114 (3)0.076 (2)0.064 (2)0.011 (2)0.037 (2)0.0002 (17)
C170.070 (2)0.069 (2)0.0679 (19)0.0066 (16)0.0279 (16)0.0324 (17)
C180.080 (2)0.079 (2)0.067 (2)0.0004 (19)0.0224 (18)0.031 (2)
C190.090 (2)0.0608 (19)0.0563 (19)0.0110 (18)0.0360 (18)0.0019 (15)
C200.075 (2)0.0526 (16)0.075 (2)0.0146 (15)0.0459 (18)0.0218 (15)
C210.066 (2)0.078 (2)0.0594 (18)0.0080 (16)0.0278 (16)0.0184 (17)
C220.081 (2)0.085 (3)0.062 (2)0.004 (2)0.0324 (18)0.0064 (19)
C230.107 (3)0.056 (2)0.085 (3)0.004 (2)0.063 (2)0.0014 (19)
C240.090 (2)0.0495 (17)0.094 (3)0.0160 (16)0.060 (2)0.0202 (17)
C250.0712 (19)0.0547 (17)0.082 (2)0.0257 (15)0.0409 (17)0.0323 (16)
C260.0590 (17)0.0530 (15)0.0609 (17)0.0114 (13)0.0313 (14)0.0269 (13)
C270.0560 (16)0.0456 (14)0.0556 (16)0.0067 (12)0.0298 (13)0.0166 (12)
C280.0565 (16)0.0528 (15)0.0554 (16)0.0078 (13)0.0311 (13)0.0175 (13)
C290.0648 (18)0.0484 (15)0.0625 (17)0.0114 (13)0.0378 (15)0.0180 (13)
Cl10.1297 (9)0.1445 (10)0.0680 (6)0.0830 (8)0.0145 (6)0.0366 (6)
Cl20.0980 (7)0.1159 (8)0.1014 (7)0.0309 (6)0.0204 (6)0.0673 (7)
O10.133 (2)0.1013 (19)0.0648 (16)0.0579 (18)0.0214 (16)0.0054 (14)
O20.0731 (13)0.0615 (12)0.0557 (12)0.0194 (10)0.0276 (10)0.0052 (10)
O30.115 (2)0.0962 (19)0.114 (2)0.0655 (17)0.0342 (17)0.0295 (16)
S10.0550 (4)0.0531 (4)0.0446 (4)0.0129 (3)0.0172 (3)0.0152 (3)
S20.0633 (5)0.0552 (4)0.0656 (5)0.0206 (3)0.0266 (4)0.0221 (4)
O40.0923 (17)0.0567 (13)0.1001 (17)0.0265 (12)0.0527 (14)0.0139 (12)
C300.081 (4)0.046 (3)0.047 (3)0.022 (2)0.024 (3)0.013 (2)
C310.087 (4)0.065 (4)0.066 (4)0.041 (3)0.028 (3)0.021 (3)
C320.154 (14)0.107 (9)0.129 (14)0.078 (8)0.031 (11)0.020 (7)
C30A0.113 (11)0.047 (6)0.098 (10)0.018 (6)0.063 (9)0.026 (7)
C31A0.108 (10)0.059 (7)0.068 (7)0.020 (6)0.043 (7)0.015 (5)
C32A0.121 (17)0.15 (2)0.052 (8)0.080 (16)0.031 (10)0.013 (11)
Geometric parameters (Å, º) top
C1—C21.361 (4)C19—C201.374 (4)
C1—C101.407 (4)C19—H190.9300
C1—Cl11.736 (3)C20—O41.351 (4)
C2—C31.383 (4)C20—C271.411 (4)
C2—H20.9300C21—C221.358 (5)
C3—C41.364 (4)C21—C281.396 (4)
C3—H30.9300C21—H210.9300
C4—O21.363 (3)C22—C231.379 (5)
C4—C111.408 (4)C22—H220.9300
C5—C61.363 (4)C23—C241.366 (5)
C5—C121.403 (4)C23—H230.9300
C5—H50.9300C24—C291.400 (4)
C6—C71.385 (4)C24—H240.9300
C6—H60.9300C25—O31.217 (4)
C7—C81.358 (4)C25—C291.472 (4)
C7—H70.9300C25—C261.475 (4)
C8—C131.399 (4)C26—C271.396 (4)
C8—H80.9300C27—S21.740 (3)
C9—O11.211 (3)C28—C291.387 (4)
C9—C131.471 (4)C28—S21.732 (3)
C9—C101.478 (4)O4—C30A1.456 (10)
C10—C111.408 (4)O4—C301.475 (5)
C11—S11.737 (3)C30—C311.502 (7)
C12—C131.390 (4)C30—H30A0.9700
C12—S11.731 (3)C30—H30B0.9700
C14—O21.435 (3)C31—C321.572 (12)
C14—C151.499 (4)C31—H31A0.9700
C14—H14A0.9700C31—H31B0.9700
C14—H14B0.9700C32—H32A0.9600
C15—C161.520 (4)C32—H32B0.9600
C15—H15A0.9700C32—H32C0.9600
C15—H15B0.9700C30A—C31A1.486 (12)
C16—H16A0.9600C30A—H30C0.9700
C16—H16B0.9600C30A—H30D0.9700
C16—H16C0.9600C31A—C32A1.595 (18)
C17—C181.342 (5)C31A—H31C0.9700
C17—C261.420 (4)C31A—H31D0.9700
C17—Cl21.735 (3)C32A—H32D0.9600
C18—C191.367 (5)C32A—H32E0.9600
C18—H180.9300C32A—H32F0.9600
C2—C1—C10122.0 (3)O4—C20—C19126.8 (3)
C2—C1—Cl1114.7 (2)O4—C20—C27113.8 (3)
C10—C1—Cl1123.3 (2)C19—C20—C27119.5 (3)
C1—C2—C3121.0 (3)C22—C21—C28120.8 (3)
C1—C2—H2119.5C22—C21—H21119.6
C3—C2—H2119.5C28—C21—H21119.6
C4—C3—C2119.3 (3)C21—C22—C23120.1 (3)
C4—C3—H3120.3C21—C22—H22120.0
C2—C3—H3120.3C23—C22—H22120.0
O2—C4—C3125.3 (3)C24—C23—C22119.9 (3)
O2—C4—C11114.2 (2)C24—C23—H23120.0
C3—C4—C11120.5 (3)C22—C23—H23120.0
C6—C5—C12120.5 (3)C23—C24—C29121.2 (3)
C6—C5—H5119.8C23—C24—H24119.4
C12—C5—H5119.8C29—C24—H24119.4
C5—C6—C7120.2 (3)O3—C25—C29118.4 (3)
C5—C6—H6119.9O3—C25—C26121.0 (3)
C7—C6—H6119.9C29—C25—C26120.7 (3)
C8—C7—C6119.6 (3)C27—C26—C17116.6 (3)
C8—C7—H7120.2C27—C26—C25121.4 (3)
C6—C7—H7120.2C17—C26—C25122.0 (3)
C7—C8—C13121.9 (3)C26—C27—C20120.6 (3)
C7—C8—H8119.1C26—C27—S2125.8 (2)
C13—C8—H8119.1C20—C27—S2113.6 (2)
O1—C9—C13118.6 (3)C29—C28—C21119.8 (3)
O1—C9—C10120.6 (3)C29—C28—S2123.9 (2)
C13—C9—C10120.8 (2)C21—C28—S2116.3 (2)
C1—C10—C11116.4 (3)C28—C29—C24118.2 (3)
C1—C10—C9122.3 (3)C28—C29—C25124.0 (2)
C11—C10—C9121.3 (2)C24—C29—C25117.7 (3)
C4—C11—C10120.7 (2)C4—O2—C14117.7 (2)
C4—C11—S1113.4 (2)C12—S1—C11103.39 (13)
C10—C11—S1125.9 (2)C28—S2—C27103.35 (14)
C13—C12—C5119.6 (3)C20—O4—C30A140.7 (7)
C13—C12—S1124.2 (2)C20—O4—C30111.5 (3)
C5—C12—S1116.2 (2)C30A—O4—C3032.6 (5)
C12—C13—C8118.1 (3)O4—C30—C31103.6 (4)
C12—C13—C9124.2 (2)O4—C30—H30A111.0
C8—C13—C9117.8 (2)C31—C30—H30A111.0
O2—C14—C15107.7 (3)O4—C30—H30B111.0
O2—C14—H14A110.2C31—C30—H30B111.0
C15—C14—H14A110.2H30A—C30—H30B109.0
O2—C14—H14B110.2C30—C31—C32106.1 (9)
C15—C14—H14B110.2C30—C31—H31A110.5
H14A—C14—H14B108.5C32—C31—H31A110.5
C14—C15—C16111.0 (3)C30—C31—H31B110.5
C14—C15—H15A109.4C32—C31—H31B110.5
C16—C15—H15A109.4H31A—C31—H31B108.7
C14—C15—H15B109.4O4—C30A—C31A107.7 (8)
C16—C15—H15B109.4O4—C30A—H30C110.2
H15A—C15—H15B108.0C31A—C30A—H30C110.2
C15—C16—H16A109.5O4—C30A—H30D110.2
C15—C16—H16B109.5C31A—C30A—H30D110.2
H16A—C16—H16B109.5H30C—C30A—H30D108.5
C15—C16—H16C109.5C30A—C31A—C32A100.4 (15)
H16A—C16—H16C109.5C30A—C31A—H31C111.7
H16B—C16—H16C109.5C32A—C31A—H31C111.7
C18—C17—C26122.1 (3)C30A—C31A—H31D111.7
C18—C17—Cl2114.6 (3)C32A—C31A—H31D111.7
C26—C17—Cl2123.3 (3)H31C—C31A—H31D109.5
C17—C18—C19120.8 (3)C31A—C32A—H32D109.4
C17—C18—H18119.6C31A—C32A—H32E109.5
C19—C18—H18119.6H32D—C32A—H32E109.5
C18—C19—C20120.4 (3)C31A—C32A—H32F109.5
C18—C19—H19119.8H32D—C32A—H32F109.5
C20—C19—H19119.8H32E—C32A—H32F109.5
 

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