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The title compound, C20H10Cl2N2S2·2C3H7NO, is a dimethyl­formamide (DMF) disolvate of DTQ-Cl, which is a thio­nated pigment derivative of 2,9-dichloro­quinacridone. The DTQ-Cl mol­ecule is centrosymmetric and entirely planar. Two DMF mol­ecules are hydrogen-bonded to DTQ-Cl, through the NH group of DTQ-Cl and the O atom of DMF. The mol­ecular plane of DMF is twisted with respect to the skeleton of DTQ-Cl by 21.4 (1)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013334/ob6512sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013334/ob6512Isup2.hkl
Contains datablock I

CCDC reference: 274602

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.096
  • Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.92
Author Response: A two-dimensional imaging-plate area dector was used for data collection along with Cu as X-ray target.

Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 68.24 From the CIF: _diffrn_reflns_theta_full 68.24 From the CIF: _reflns_number_total 2123 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2327 Completeness (_total/calc) 91.23% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C12 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.16 Ratio
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 3 ALERT type 3 Indicator that the structure quality may be low 2 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 and Rigaku, 2004); 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-Dichloroquino[2,3-b]acridine-7,14(5H,12H)-dithione dimethylformamide disolvate top
Crystal data top
C20H10Cl2N2S2·2C3H7NOF(000) = 1160.00
Mr = 559.53Dx = 1.461 Mg m3
Monoclinic, C2/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2ycCell parameters from 9508 reflections
a = 33.257 (4) Åθ = 3.2–68.3°
b = 4.2682 (6) ŵ = 4.10 mm1
c = 21.589 (3) ÅT = 93 K
β = 123.872 (7)°Needle, dark green
V = 2544.4 (6) Å30.50 × 0.10 × 0.05 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID-F imaging plate
diffractometer
1947 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.028
72 frames, Δ ω = 10° scansθmax = 68.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 4040
Tmin = 0.280, Tmax = 0.815k = 44
11564 measured reflectionsl = 2425
2123 independent reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.0528P)2 + 3.2176P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096(Δ/σ)max < 0.001
S = 1.10Δρmax = 0.40 e Å3
2123 reflectionsΔρmin = 0.31 e Å3
170 parameters
Special details top

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>2σ(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
Cl10.23950 (2)1.2586 (1)0.38724 (2)0.0301 (2)
S10.04395 (2)1.4752 (1)0.18846 (3)0.0260 (2)
O10.12769 (5)0.4279 (4)0.01639 (8)0.0339 (4)
N10.09608 (5)0.8195 (5)0.08319 (9)0.0211 (4)
N20.11570 (6)0.1267 (5)0.07963 (9)0.0269 (4)
C10.14895 (7)1.2313 (5)0.2621 (1)0.0228 (5)
C20.19577 (7)1.1269 (6)0.2974 (1)0.0242 (5)
C30.21016 (7)0.9214 (5)0.2624 (1)0.0244 (5)
C40.17701 (7)0.8247 (5)0.1912 (1)0.0232 (4)
C50.12823 (6)0.9262 (5)0.1534 (1)0.0203 (4)
C90.04843 (6)0.9109 (5)0.0422 (1)0.0198 (4)
C80.03123 (6)1.1173 (5)0.0739 (1)0.0194 (4)
C70.06356 (7)1.2359 (5)0.1499 (1)0.0197 (4)
C60.11368 (6)1.1307 (5)0.1888 (1)0.0206 (4)
C100.01749 (7)0.7979 (5)0.0302 (1)0.0204 (4)
C110.10143 (8)0.2758 (5)0.0413 (1)0.0290 (5)
C120.16620 (8)0.1246 (7)0.0547 (1)0.0385 (6)
C130.08160 (9)0.0390 (6)0.1486 (1)0.0352 (6)
H10.14021.37140.28690.027*
H1N0.1054 (8)0.703 (6)0.064 (1)0.026 (6)*
H30.24270.85030.28820.029*
H40.18660.68880.16690.028*
H100.02990.65970.05020.025*
H110.06800.26450.05980.035*
H12B0.16950.22230.09270.046*
H12C0.17790.09210.04660.046*
H12A0.18540.24210.00790.046*
H13B0.09250.25570.14490.042*
H13C0.07990.06550.19040.042*
H13A0.04950.03840.15680.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0198 (3)0.0409 (4)0.0203 (3)0.0048 (2)0.0054 (2)0.0033 (2)
S10.0247 (3)0.0288 (4)0.0207 (3)0.0014 (2)0.0104 (2)0.0017 (2)
O10.0370 (8)0.035 (1)0.0330 (8)0.0024 (7)0.0212 (7)0.0054 (7)
N10.0167 (8)0.026 (1)0.0189 (8)0.0018 (7)0.0089 (7)0.0014 (7)
N20.0309 (9)0.026 (1)0.0246 (8)0.0039 (8)0.0162 (7)0.0011 (7)
C10.024 (1)0.023 (1)0.0208 (9)0.0027 (8)0.0119 (8)0.0005 (8)
C20.0185 (9)0.030 (1)0.0189 (9)0.0058 (8)0.0072 (8)0.0011 (8)
C30.0166 (9)0.028 (1)0.025 (1)0.0017 (8)0.0094 (8)0.0047 (8)
C40.0194 (9)0.025 (1)0.025 (1)0.0007 (8)0.0126 (8)0.0024 (8)
C50.0187 (9)0.021 (1)0.0201 (9)0.0021 (8)0.0100 (8)0.0031 (8)
C90.0187 (9)0.019 (1)0.0205 (9)0.0012 (8)0.0103 (8)0.0042 (8)
C80.0177 (9)0.020 (1)0.0187 (9)0.0015 (8)0.0092 (7)0.0017 (8)
C70.0201 (9)0.018 (1)0.021 (1)0.0018 (7)0.0114 (8)0.0028 (8)
C60.0185 (9)0.022 (1)0.0197 (9)0.0020 (8)0.0094 (8)0.0032 (8)
C100.0210 (9)0.021 (1)0.0198 (9)0.0001 (8)0.0117 (8)0.0004 (8)
C110.034 (1)0.026 (1)0.033 (1)0.0020 (9)0.023 (1)0.0034 (9)
C120.035 (1)0.047 (2)0.036 (1)0.010 (1)0.021 (1)0.001 (1)
C130.045 (1)0.030 (2)0.029 (1)0.001 (1)0.019 (1)0.001 (1)
Geometric parameters (Å, º) top
Cl1—C21.746 (2)C8—C71.462 (2)
S1—C71.663 (3)C8—C10i1.394 (3)
O1—C111.234 (2)C7—C81.462 (2)
N1—C51.357 (2)C7—C61.458 (3)
N1—C91.372 (2)C10—C8i1.394 (3)
N2—C111.325 (4)N1—H1N0.82 (3)
N2—C121.450 (3)C1—H10.9498
N2—C131.456 (3)C3—H30.9498
C1—C21.371 (3)C4—H40.9500
C1—C61.413 (2)C10—H100.9498
C2—C31.404 (4)C11—H110.9501
C3—C41.364 (3)C12—H12B0.9801
C4—C51.418 (3)C12—H12C0.9800
C5—C61.411 (3)C12—H12A0.9799
C9—C81.418 (3)C13—H13B0.9800
C9—C101.393 (2)C13—H13C0.9800
C8—C91.418 (3)C13—H13A0.9801
Cl1—C2—C1119.9 (2)C10—C8i—C9i117.6 (2)
Cl1—C2—C3118.4 (1)C10—C8i—C7i121.4 (2)
S1—C7—C8121.7 (2)O1—C11—H11117.1059
S1—C7—C6122.9 (1)H1N—N1—C5119 (1)
O1—C11—N2125.8 (2)H1N—N1—C9118 (1)
N1—C5—C6121.2 (2)N2—C11—H11117.0985
N1—C5—C4118.5 (2)N2—C12—H12B109.4631
C9—N1—C5122.2 (2)N2—C12—H12C109.4680
N1—C9—C8119.8 (2)N2—C12—H12A109.4723
N1—C9—C10119.4 (2)N2—C13—H13B109.4629
C12—N2—C11121.0 (2)N2—C13—H13C109.4649
C13—N2—C11121.8 (2)N2—C13—H13A109.4746
C13—N2—C12117.2 (2)H1—C1—C2119.9649
C1—C2—C3121.7 (2)H1—C1—C6119.9842
C6—C1—C2120.1 (2)C2—C3—H3120.2723
C1—C6—C7121.4 (2)H3—C3—C4120.2864
C1—C6—C5118.2 (2)C3—C4—H4119.8818
C2—C3—C4119.4 (2)H4—C4—C5119.8882
C3—C4—C5120.2 (2)C9—C10—H10119.2251
C4—C5—C6120.3 (2)C8—C10i—H10i119.2225
C5—C6—C7120.4 (2)H10—C10—C8i119.2225
C9—C8—C7121.0 (2)H12C—C12—H12B109.4707
C9—C8—C10i117.6 (2)H12A—C12—H12B109.4774
C10—C9—C8120.8 (2)H12A—C12—H12C109.4757
C9—C10—C8i121.6 (2)H13C—C13—H13B109.4704
C8—C7—C6115.4 (2)H13A—C13—H13B109.4773
C10i—C8—C7121.4 (2)H13A—C13—H13C109.4773
C8—C10i—C9i121.6 (2)
Symmetry code: (i) x, y+2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.82 (2)1.95 (3)2.769 (2)180 (3)
 

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