2,9-Dichloro­quino[2,3-b]acridine-7,14(5H,12H)-dithione dimethyl­formamide disolvate

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)°.

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

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Computing details

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

Crystal data

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) Å^3	0.50 × 0.10 × 0.05 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID-F imaging plate diffractometer	1947 reflections with F^2 > 2σ(F^2)
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

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.0528P)^2 + 3.2176P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Cl1—C2	1.746 (2)	C8—C7	1.462 (2)
S1—C7	1.663 (3)	C8—C10^i	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—C8^i	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—C8^i—C9^i	117.6 (2)
Cl1—C2—C3	118.4 (1)	C10—C8^i—C7^i	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—C10^i—H10^i	119.2225
C5—C6—C7	120.4 (2)	H10—C10—C8^i	119.2225
C9—C8—C7	121.0 (2)	H12C—C12—H12B	109.4707
C9—C8—C10^i	117.6 (2)	H12A—C12—H12B	109.4774
C10—C9—C8	120.8 (2)	H12A—C12—H12C	109.4757
C9—C10—C8^i	121.6 (2)	H13C—C13—H13B	109.4704
C8—C7—C6	115.4 (2)	H13A—C13—H13B	109.4773
C10^i—C8—C7	121.4 (2)	H13A—C13—H13C	109.4773
C8—C10^i—C9^i	121.6 (2)

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º)

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)