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The title compound, C20H10Cl2N2S2·2C4H9NO, is a dimethyl­acetamide (DMA) disolvate of DTQ-Cl, which is a thio­nated derivative of a 2,9-dichloro­quinacridone pigment. The compound shows polymorphism and this paper reports the triclinic form (space group P\overline{1}, Z = 1). The DTQ-Cl mol­ecule is centrosymmetric and planar, while the DMA mol­ecule is orientationally disordered. Two symmetry-related DMA mol­ecules are hydrogen bonded via their O atoms to the NH groups of DTQ-Cl. The mol­ecular plane of DMA is twisted with respect to the DTQ-Cl skeleton by 73.6 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805016636/ob6520sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805016636/ob6520Isup2.hkl
Contains datablock I

CCDC reference: 274608

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in solvent or counterion
  • R factor = 0.061
  • wR factor = 0.216
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.89
Author Response: A two-dmensional detector (IP) was used in combination with Cu as radiation.

Alert level B REFLT03_ALERT_3_B Reflection count < 90% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 68.11 From the CIF: _diffrn_reflns_theta_full 68.11 From the CIF: _reflns_number_total 2164 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2427 Completeness (_total/calc) 89.16% PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low .... 0.89
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 2 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C11 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C13 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 25.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 68.11 From the CIF: _reflns_number_total 2164 From the CIF: _diffrn_reflns_limit_ max hkl 8. 10. 10. From the CIF: _diffrn_reflns_limit_ min hkl -8. -10. -11. TEST1: Expected hkl limits for theta max Calculated maximum hkl 8. 10. 13. Calculated minimum hkl -8. -10. -13.
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 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 5 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

2,9-dichloro-5,12-dihydroquino[2,3-b]acridine- 7,14-dithione dimethylacetamide disolvate top
Crystal data top
C20H10Cl2N2S2·2C4H9NOZ = 1
Mr = 587.58F(000) = 306.00
Triclinic, P1Dx = 1.468 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.5418 Å
a = 7.156 (2) ÅCell parameters from 5253 reflections
b = 8.941 (3) Åθ = 4.1–68.0°
c = 11.487 (4) ŵ = 3.95 mm1
α = 104.32 (2)°T = 93 K
β = 96.91 (2)°Platelet, dark green
γ = 107.369 (18)°0.40 × 0.40 × 0.08 mm
V = 664.5 (4) Å3
Data collection top
Rigaku R-AXIS RAPID-F imaging-plate
diffractometer
1551 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.039
72 frames, Δ ω = 10° scansθmax = 68.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 88
Tmin = 0.281, Tmax = 0.729k = 1010
5955 measured reflectionsl = 1110
2164 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.061 w = 1/[σ2(Fo2) + (0.1319P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.217(Δ/σ)max < 0.001
S = 1.18Δρmax = 0.46 e Å3
2164 reflectionsΔρmin = 0.53 e Å3
171 parameters
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

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)
Cl10.05006 (15)0.06167 (11)0.16885 (10)0.0425 (4)
S10.11519 (16)0.63783 (12)0.28496 (10)0.0454 (4)
O10.6372 (4)0.8346 (4)0.3447 (3)0.0475 (8)
N10.4336 (4)0.7451 (4)0.1031 (3)0.0299 (8)
H1N0.48940.76670.18070.036*
C10.1058 (5)0.3828 (4)0.1471 (4)0.0336 (10)
H10.03900.35250.23050.040*
C20.0910 (5)0.2668 (4)0.0882 (4)0.0331 (9)
C30.1858 (6)0.3040 (5)0.0335 (4)0.0376 (10)
H30.17310.21990.07200.045*
C40.2984 (5)0.4645 (4)0.0974 (4)0.0328 (9)
H40.36280.49190.18090.039*
C50.3185 (5)0.5890 (4)0.0389 (4)0.0303 (9)
C60.2213 (5)0.5492 (4)0.0838 (4)0.0302 (9)
C70.2383 (5)0.6751 (4)0.1460 (4)0.0336 (10)
C80.3711 (5)0.8413 (4)0.0718 (4)0.0297 (9)
C90.4662 (5)0.8708 (5)0.0513 (4)0.0305 (9)
C100.4063 (5)0.9725 (4)0.1203 (4)0.0320 (9)
H100.34200.95490.20230.038*
C110.8909 (6)0.7842 (6)0.4931 (5)0.0612 (14)
H11A0.96660.76070.55910.092*0.623 (13)
H11B0.95780.89710.49300.092*0.623 (13)
H11C0.88420.70780.41390.092*0.623 (13)
H11D0.87660.75890.57060.092*0.377 (13)
H11E1.00360.88640.50890.092*0.377 (13)
H11F0.91580.69440.43600.092*0.377 (13)
C120.6031 (6)0.7082 (5)0.6163 (4)0.0446 (11)
H12A0.71110.69360.66850.067*0.623 (13)
H12B0.49200.60350.58260.067*0.623 (13)
H12C0.55620.79050.66530.067*0.623 (13)
H12D0.48320.67980.65090.067*0.377 (13)
H12E0.71070.79900.67760.067*0.377 (13)
H12F0.64610.61250.59370.067*0.377 (13)
C130.3557 (6)0.7754 (6)0.4540 (5)0.0582 (14)
H13A0.34230.74130.52820.087*0.623 (13)
H13B0.25560.69270.38370.087*0.623 (13)
H13C0.33490.88120.46550.087*0.623 (13)
H13D0.25810.74170.50370.087*0.377 (13)
H13E0.30460.70530.36860.087*0.377 (13)
H13F0.37770.89000.45710.087*0.377 (13)
N20.6791 (10)0.7641 (6)0.5140 (6)0.0385 (19)*0.623 (13)
C140.5668 (11)0.7929 (8)0.4295 (7)0.041 (2)*0.623 (13)
N30.5569 (15)0.7585 (10)0.5055 (9)0.031 (3)*0.377 (13)
C150.6937 (17)0.8049 (12)0.4354 (11)0.032 (3)*0.377 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0476 (7)0.0311 (5)0.0499 (9)0.0117 (4)0.0148 (5)0.0141 (5)
S10.0514 (7)0.0400 (6)0.0436 (9)0.0125 (5)0.0086 (5)0.0149 (5)
O10.0568 (19)0.0545 (19)0.032 (2)0.0167 (15)0.0078 (15)0.0185 (15)
N10.0371 (17)0.0338 (16)0.024 (2)0.0159 (13)0.0071 (13)0.0123 (14)
C10.032 (2)0.036 (2)0.038 (3)0.0159 (16)0.0148 (18)0.0113 (18)
C20.039 (2)0.034 (2)0.031 (3)0.0160 (17)0.0126 (18)0.0104 (17)
C30.040 (2)0.035 (2)0.051 (3)0.0189 (17)0.023 (2)0.021 (2)
C40.038 (2)0.035 (2)0.034 (3)0.0163 (17)0.0159 (18)0.0180 (18)
C50.032 (2)0.037 (2)0.033 (3)0.0185 (16)0.0154 (17)0.0163 (18)
C60.0292 (19)0.0322 (19)0.034 (3)0.0137 (15)0.0119 (17)0.0124 (17)
C70.031 (2)0.033 (2)0.041 (3)0.0150 (16)0.0112 (18)0.0131 (18)
C80.032 (2)0.0324 (19)0.030 (3)0.0137 (15)0.0111 (16)0.0120 (17)
C90.032 (2)0.037 (2)0.032 (3)0.0195 (16)0.0114 (17)0.0132 (17)
C100.037 (2)0.037 (2)0.031 (3)0.0197 (17)0.0105 (18)0.0143 (18)
C110.040 (3)0.069 (3)0.063 (4)0.023 (2)0.006 (2)0.003 (3)
C120.045 (2)0.047 (2)0.045 (3)0.0164 (19)0.011 (2)0.017 (2)
C130.033 (2)0.058 (3)0.073 (4)0.017 (2)0.005 (2)0.004 (3)
Geometric parameters (Å, º) top
Cl1—C21.752 (4)C11—H11A0.9800
S1—C71.630 (4)C11—H11B0.9800
O1—C151.191 (11)C11—H11C0.9800
O1—C141.236 (8)C11—H11D0.9800
N1—C51.352 (5)C11—H11E0.9800
N1—C91.370 (4)C11—H11F0.9800
N1—H1N0.8800C12—N31.485 (10)
C1—C21.358 (5)C12—N21.487 (7)
C1—C61.418 (5)C12—H12A0.9800
C1—H10.9500C12—H12B0.9800
C2—C31.390 (6)C12—H12C0.9800
C3—C41.376 (5)C12—H12D0.9800
C3—H30.9500C12—H12E0.9800
C4—C51.417 (5)C12—H12F0.9800
C4—H40.9500C13—C141.539 (8)
C5—C61.402 (6)C13—N31.554 (10)
C6—C71.459 (5)C13—H13A0.9800
C7—C81.475 (5)C13—H13B0.9800
C8—C101.389 (5)C13—H13C0.9800
C8—C91.417 (6)C13—H13D0.9800
C9—C10i1.392 (5)C13—H13E0.9800
C10—H100.9500C13—H13F0.9800
C11—N21.527 (7)N2—C141.309 (12)
C11—C151.568 (12)N3—C151.376 (18)
C5—N1—C9122.2 (3)H11D—C11—H11E109.5
C5—N1—H1N118.9C15—C11—H11F109.5
C9—N1—H1N118.9H11D—C11—H11F109.5
C2—C1—C6119.8 (4)H11E—C11—H11F109.5
C2—C1—H1120.1N2—C12—H12A109.5
C6—C1—H1120.1N2—C12—H12B109.5
C1—C2—C3122.5 (4)H12A—C12—H12B109.5
C1—C2—Cl1118.9 (3)N2—C12—H12C109.5
C3—C2—Cl1118.5 (3)H12A—C12—H12C109.5
C4—C3—C2119.0 (4)H12B—C12—H12C109.5
C4—C3—H3120.5N3—C12—H12D109.5
C2—C3—H3120.5N3—C12—H12E109.5
C3—C4—C5120.2 (4)H12D—C12—H12E109.5
C3—C4—H4119.9N3—C12—H12F109.5
C5—C4—H4119.9H12D—C12—H12F109.5
N1—C5—C6121.1 (3)H12E—C12—H12F109.5
N1—C5—C4118.9 (4)C14—C13—H13A109.5
C6—C5—C4120.0 (4)C14—C13—H13B109.5
C5—C6—C1118.5 (4)H13A—C13—H13B109.5
C5—C6—C7121.2 (3)C14—C13—H13C109.5
C1—C6—C7120.3 (4)H13A—C13—H13C109.5
C6—C7—C8114.8 (4)H13B—C13—H13C109.5
C6—C7—S1123.1 (3)N3—C13—H13D109.5
C8—C7—S1122.1 (3)N3—C13—H13E109.5
C10—C8—C9118.4 (4)H13D—C13—H13E109.5
C10—C8—C7121.1 (4)N3—C13—H13F109.5
C9—C8—C7120.5 (3)H13D—C13—H13F109.5
N1—C9—C10i119.6 (4)H13E—C13—H13F109.5
N1—C9—C8120.2 (4)C14—N2—C12122.8 (7)
C10i—C9—C8120.2 (3)C14—N2—C11113.6 (6)
C8—C10—C9i121.4 (4)C12—N2—C11123.5 (5)
C8—C10—H10119.3O1—C14—N2119.8 (7)
C9i—C10—H10119.3O1—C14—C13127.5 (7)
N2—C11—H11A109.5N2—C14—C13112.6 (7)
N2—C11—H11B109.5C15—N3—C12123.8 (9)
H11A—C11—H11B109.5C15—N3—C13109.5 (8)
N2—C11—H11C109.5C12—N3—C13126.6 (7)
H11A—C11—H11C109.5O1—C15—N3118.0 (10)
H11B—C11—H11C109.5O1—C15—C11135.3 (10)
C15—C11—H11D109.5N3—C15—C11106.2 (9)
C15—C11—H11E109.5
Symmetry code: (i) x+1, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.881.902.774 (4)173
 

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