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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
CCDC reference: 274602
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (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
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(5
H,12H)-dithione
dimethylformamide disolvate
top
Crystal data top
C20H10Cl2N2S2·2C3H7NO | F(000) = 1160.00 |
Mr = 559.53 | Dx = 1.461 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -C 2yc | Cell parameters from 9508 reflections |
a = 33.257 (4) Å | θ = 3.2–68.3° |
b = 4.2682 (6) Å | µ = 4.10 mm−1 |
c = 21.589 (3) Å | T = 93 K |
β = 123.872 (7)° | Needle, dark green |
V = 2544.4 (6) Å3 | 0.50 × 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-1 | Rint = 0.028 |
72 frames, Δ ω = 10° scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −40→40 |
Tmin = 0.280, Tmax = 0.815 | k = −4→4 |
11564 measured reflections | l = −24→25 |
2123 independent reflections | |
Refinement top
Refinement on F2 | H 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 = 1.10 | Δρmax = 0.40 e Å−3 |
2123 reflections | Δρmin = −0.31 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.23950 (2) | 1.2586 (1) | 0.38724 (2) | 0.0301 (2) | |
S1 | 0.04395 (2) | 1.4752 (1) | 0.18846 (3) | 0.0260 (2) | |
O1 | 0.12769 (5) | 0.4279 (4) | 0.01639 (8) | 0.0339 (4) | |
N1 | 0.09608 (5) | 0.8195 (5) | 0.08319 (9) | 0.0211 (4) | |
N2 | 0.11570 (6) | 0.1267 (5) | −0.07963 (9) | 0.0269 (4) | |
C1 | 0.14895 (7) | 1.2313 (5) | 0.2621 (1) | 0.0228 (5) | |
C2 | 0.19577 (7) | 1.1269 (6) | 0.2974 (1) | 0.0242 (5) | |
C3 | 0.21016 (7) | 0.9214 (5) | 0.2624 (1) | 0.0244 (5) | |
C4 | 0.17701 (7) | 0.8247 (5) | 0.1912 (1) | 0.0232 (4) | |
C5 | 0.12823 (6) | 0.9262 (5) | 0.1534 (1) | 0.0203 (4) | |
C9 | 0.04843 (6) | 0.9109 (5) | 0.0422 (1) | 0.0198 (4) | |
C8 | 0.03123 (6) | 1.1173 (5) | 0.0739 (1) | 0.0194 (4) | |
C7 | 0.06356 (7) | 1.2359 (5) | 0.1499 (1) | 0.0197 (4) | |
C6 | 0.11368 (6) | 1.1307 (5) | 0.1888 (1) | 0.0206 (4) | |
C10 | 0.01749 (7) | 0.7979 (5) | −0.0302 (1) | 0.0204 (4) | |
C11 | 0.10143 (8) | 0.2758 (5) | −0.0413 (1) | 0.0290 (5) | |
C12 | 0.16620 (8) | 0.1246 (7) | −0.0547 (1) | 0.0385 (6) | |
C13 | 0.08160 (9) | −0.0390 (6) | −0.1486 (1) | 0.0352 (6) | |
H1 | 0.1402 | 1.3714 | 0.2869 | 0.027* | |
H1N | 0.1054 (8) | 0.703 (6) | 0.064 (1) | 0.026 (6)* | |
H3 | 0.2427 | 0.8503 | 0.2882 | 0.029* | |
H4 | 0.1866 | 0.6888 | 0.1669 | 0.028* | |
H10 | 0.0299 | 0.6597 | −0.0502 | 0.025* | |
H11 | 0.0680 | 0.2645 | −0.0598 | 0.035* | |
H12B | 0.1695 | 0.2223 | −0.0927 | 0.046* | |
H12C | 0.1779 | −0.0921 | −0.0466 | 0.046* | |
H12A | 0.1854 | 0.2421 | −0.0079 | 0.046* | |
H13B | 0.0925 | −0.2557 | −0.1449 | 0.042* | |
H13C | 0.0799 | 0.0655 | −0.1904 | 0.042* | |
H13A | 0.0495 | −0.0384 | −0.1568 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0198 (3) | 0.0409 (4) | 0.0203 (3) | −0.0048 (2) | 0.0054 (2) | −0.0033 (2) |
S1 | 0.0247 (3) | 0.0288 (4) | 0.0207 (3) | 0.0014 (2) | 0.0104 (2) | −0.0017 (2) |
O1 | 0.0370 (8) | 0.035 (1) | 0.0330 (8) | 0.0024 (7) | 0.0212 (7) | −0.0054 (7) |
N1 | 0.0167 (8) | 0.026 (1) | 0.0189 (8) | 0.0018 (7) | 0.0089 (7) | −0.0014 (7) |
N2 | 0.0309 (9) | 0.026 (1) | 0.0246 (8) | 0.0039 (8) | 0.0162 (7) | 0.0011 (7) |
C1 | 0.024 (1) | 0.023 (1) | 0.0208 (9) | −0.0027 (8) | 0.0119 (8) | 0.0005 (8) |
C2 | 0.0185 (9) | 0.030 (1) | 0.0189 (9) | −0.0058 (8) | 0.0072 (8) | 0.0011 (8) |
C3 | 0.0166 (9) | 0.028 (1) | 0.025 (1) | −0.0017 (8) | 0.0094 (8) | 0.0047 (8) |
C4 | 0.0194 (9) | 0.025 (1) | 0.025 (1) | 0.0007 (8) | 0.0126 (8) | 0.0024 (8) |
C5 | 0.0187 (9) | 0.021 (1) | 0.0201 (9) | −0.0021 (8) | 0.0100 (8) | 0.0031 (8) |
C9 | 0.0187 (9) | 0.019 (1) | 0.0205 (9) | 0.0012 (8) | 0.0103 (8) | 0.0042 (8) |
C8 | 0.0177 (9) | 0.020 (1) | 0.0187 (9) | −0.0015 (8) | 0.0092 (7) | 0.0017 (8) |
C7 | 0.0201 (9) | 0.018 (1) | 0.021 (1) | −0.0018 (7) | 0.0114 (8) | 0.0028 (8) |
C6 | 0.0185 (9) | 0.022 (1) | 0.0197 (9) | −0.0020 (8) | 0.0094 (8) | 0.0032 (8) |
C10 | 0.0210 (9) | 0.021 (1) | 0.0198 (9) | 0.0001 (8) | 0.0117 (8) | 0.0004 (8) |
C11 | 0.034 (1) | 0.026 (1) | 0.033 (1) | 0.0020 (9) | 0.023 (1) | 0.0034 (9) |
C12 | 0.035 (1) | 0.047 (2) | 0.036 (1) | 0.010 (1) | 0.021 (1) | −0.001 (1) |
C13 | 0.045 (1) | 0.030 (2) | 0.029 (1) | 0.001 (1) | 0.019 (1) | −0.001 (1) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.746 (2) | C8—C7 | 1.462 (2) |
S1—C7 | 1.663 (3) | C8—C10i | 1.394 (3) |
O1—C11 | 1.234 (2) | C7—C8 | 1.462 (2) |
N1—C5 | 1.357 (2) | C7—C6 | 1.458 (3) |
N1—C9 | 1.372 (2) | C10—C8i | 1.394 (3) |
N2—C11 | 1.325 (4) | N1—H1N | 0.82 (3) |
N2—C12 | 1.450 (3) | C1—H1 | 0.9498 |
N2—C13 | 1.456 (3) | C3—H3 | 0.9498 |
C1—C2 | 1.371 (3) | C4—H4 | 0.9500 |
C1—C6 | 1.413 (2) | C10—H10 | 0.9498 |
C2—C3 | 1.404 (4) | C11—H11 | 0.9501 |
C3—C4 | 1.364 (3) | C12—H12B | 0.9801 |
C4—C5 | 1.418 (3) | C12—H12C | 0.9800 |
C5—C6 | 1.411 (3) | C12—H12A | 0.9799 |
C9—C8 | 1.418 (3) | C13—H13B | 0.9800 |
C9—C10 | 1.393 (2) | C13—H13C | 0.9800 |
C8—C9 | 1.418 (3) | C13—H13A | 0.9801 |
| | | |
Cl1—C2—C1 | 119.9 (2) | C10—C8i—C9i | 117.6 (2) |
Cl1—C2—C3 | 118.4 (1) | C10—C8i—C7i | 121.4 (2) |
S1—C7—C8 | 121.7 (2) | O1—C11—H11 | 117.1059 |
S1—C7—C6 | 122.9 (1) | H1N—N1—C5 | 119 (1) |
O1—C11—N2 | 125.8 (2) | H1N—N1—C9 | 118 (1) |
N1—C5—C6 | 121.2 (2) | N2—C11—H11 | 117.0985 |
N1—C5—C4 | 118.5 (2) | N2—C12—H12B | 109.4631 |
C9—N1—C5 | 122.2 (2) | N2—C12—H12C | 109.4680 |
N1—C9—C8 | 119.8 (2) | N2—C12—H12A | 109.4723 |
N1—C9—C10 | 119.4 (2) | N2—C13—H13B | 109.4629 |
C12—N2—C11 | 121.0 (2) | N2—C13—H13C | 109.4649 |
C13—N2—C11 | 121.8 (2) | N2—C13—H13A | 109.4746 |
C13—N2—C12 | 117.2 (2) | H1—C1—C2 | 119.9649 |
C1—C2—C3 | 121.7 (2) | H1—C1—C6 | 119.9842 |
C6—C1—C2 | 120.1 (2) | C2—C3—H3 | 120.2723 |
C1—C6—C7 | 121.4 (2) | H3—C3—C4 | 120.2864 |
C1—C6—C5 | 118.2 (2) | C3—C4—H4 | 119.8818 |
C2—C3—C4 | 119.4 (2) | H4—C4—C5 | 119.8882 |
C3—C4—C5 | 120.2 (2) | C9—C10—H10 | 119.2251 |
C4—C5—C6 | 120.3 (2) | C8—C10i—H10i | 119.2225 |
C5—C6—C7 | 120.4 (2) | H10—C10—C8i | 119.2225 |
C9—C8—C7 | 121.0 (2) | H12C—C12—H12B | 109.4707 |
C9—C8—C10i | 117.6 (2) | H12A—C12—H12B | 109.4774 |
C10—C9—C8 | 120.8 (2) | H12A—C12—H12C | 109.4757 |
C9—C10—C8i | 121.6 (2) | H13C—C13—H13B | 109.4704 |
C8—C7—C6 | 115.4 (2) | H13A—C13—H13B | 109.4773 |
C10i—C8—C7 | 121.4 (2) | H13A—C13—H13C | 109.4773 |
C8—C10i—C9i | 121.6 (2) | | |
Symmetry code: (i) −x, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.82 (2) | 1.95 (3) | 2.769 (2) | 180 (3) |
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