The monoclinic form of 2,9-dichloro-5,12-dihydro­quino[2,3-b]acridine-7,14-dithione dimethyl­acetamide disolvate

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 monoclinic form (space group P2₁/c, Z = 4). Two DMA mol­ecules are hydrogen bonded via their O atoms to the NH group of DTQ-Cl. The mol­ecular planes of the two DMA mol­ecules are asymmetrically twisted with respect to the DTQ-Cl skeleton by 11.65 (8) and 31.58 (9)°.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.044
• wR factor = 0.137
• Data-to-parameter ratio = 13.2

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-dmensional detector (IP) was used in combination with Cu as radiation.

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               4612
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         5004
           Completeness (_total/calc)             92.17%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.92
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.13

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   1 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
   0 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, 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

Crystal data

C20H10Cl2N2S2·2C4H9NO	F(000) = 1224.00
Mr = 587.58	Dx = 1.429 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 19515 reflections
a = 14.0463 (12) Å	θ = 3.1–68.3°
b = 7.7507 (7) Å	µ = 3.85 mm^−1
c = 25.092 (2) Å	T = 93 K
β = 90.446 (6)°	Needle, dark green
V = 2731.7 (4) Å^3	0.50 × 0.10 × 0.10 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID-F imaging-plate diffractometer	3911 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.030
72 frames, Δ ω = 10° scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −16→16
Tmin = 0.321, Tmax = 0.681	k = −7→8
23140 measured reflections	l = −30→30
4612 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0744P)^2 + 2.5397P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.137	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.48 e Å^−3
4612 reflections	Δρmin = −0.50 e Å^−3
350 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 > 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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.31915 (4)	0.98134 (10)	0.65880 (3)	0.0313 (2)
Cl2	1.20586 (4)	0.00445 (9)	0.44974 (2)	0.02472 (17)
S1	0.67247 (5)	0.69825 (11)	0.69181 (3)	0.0340 (2)
S2	0.85577 (5)	0.30492 (10)	0.41359 (3)	0.0293 (2)
O1	0.52070 (13)	0.6682 (2)	0.41596 (6)	0.0339 (5)
O2	0.98636 (17)	0.4244 (3)	0.69248 (8)	0.0549 (7)
N1	0.59619 (13)	0.6525 (2)	0.51718 (8)	0.0224 (4)
N2	0.94062 (13)	0.3863 (2)	0.58548 (8)	0.0206 (4)
N3	0.44725 (17)	0.7415 (3)	0.33991 (9)	0.0310 (5)
N4	1.08184 (19)	0.4799 (4)	0.76176 (10)	0.0458 (7)
C1	0.48829 (18)	0.8322 (3)	0.63809 (10)	0.0227 (5)
C2	0.40373 (17)	0.8875 (3)	0.61712 (10)	0.0237 (5)
C3	0.38215 (19)	0.8679 (3)	0.56276 (11)	0.0274 (6)
C4	0.44689 (18)	0.7933 (3)	0.52976 (10)	0.0258 (6)
C5	0.53464 (17)	0.7320 (3)	0.55041 (10)	0.0217 (5)
C6	0.68105 (17)	0.5845 (3)	0.53448 (9)	0.0199 (5)
C7	0.73949 (17)	0.4993 (3)	0.49837 (9)	0.0198 (5)
C8	0.82642 (16)	0.4294 (3)	0.51424 (9)	0.0181 (5)
C9	0.88739 (17)	0.3363 (3)	0.47698 (9)	0.0197 (5)
C10	0.97744 (17)	0.2723 (3)	0.49884 (10)	0.0202 (5)
C11	1.04261 (17)	0.1799 (3)	0.46707 (10)	0.0211 (5)
C12	1.12586 (17)	0.1203 (3)	0.48872 (10)	0.0208 (5)
C13	1.14870 (18)	0.1484 (3)	0.54272 (10)	0.0235 (5)
C14	1.08728 (18)	0.2369 (3)	0.57423 (10)	0.0232 (5)
C15	1.00044 (17)	0.2999 (3)	0.55294 (9)	0.0202 (5)
C16	0.85483 (17)	0.4511 (3)	0.56838 (10)	0.0199 (5)
C17	0.79643 (17)	0.5351 (3)	0.60454 (10)	0.0206 (5)
C18	0.70829 (17)	0.6011 (3)	0.58905 (9)	0.0198 (5)
C19	0.64510 (18)	0.6840 (3)	0.62689 (10)	0.0218 (5)
C20	0.55636 (17)	0.7506 (3)	0.60513 (9)	0.0201 (5)
C21	0.51881 (19)	0.6669 (3)	0.36670 (10)	0.0256 (6)
C22	0.5969 (2)	0.5816 (4)	0.33568 (12)	0.0373 (7)
C23	0.3674 (2)	0.8159 (4)	0.36826 (12)	0.0393 (7)
C24	0.4386 (2)	0.7380 (5)	0.28195 (12)	0.0536 (9)
C25	0.9970 (2)	0.4547 (4)	0.74046 (12)	0.0420 (8)
C26	0.9118 (2)	0.4665 (5)	0.77686 (13)	0.0530 (9)
C27	1.1650 (2)	0.4801 (5)	0.72684 (13)	0.0529 (9)
C28	1.1004 (2)	0.5027 (5)	0.81886 (12)	0.0562 (10)
H1N	0.5811	0.6442	0.4832	0.027*
H2N	0.9575	0.4015	0.6190	0.025*
H1	0.5016	0.8484	0.6749	0.027*
H3	0.3227	0.9065	0.5490	0.033*
H4	0.4331	0.7823	0.4928	0.031*
H7	0.7196	0.4888	0.4622	0.024*
H11	1.0285	0.1591	0.4305	0.025*
H13	1.2068	0.1057	0.5571	0.028*
H14	1.1027	0.2564	0.6107	0.028*
H17	0.8170	0.5477	0.6405	0.025*
H22A	0.6229	0.6637	0.3099	0.045*
H22B	0.5712	0.4811	0.3167	0.045*
H22C	0.6475	0.5444	0.3602	0.045*
H23A	0.3499	0.9264	0.3519	0.047*
H23B	0.3853	0.8346	0.4056	0.047*
H23C	0.3130	0.7369	0.3664	0.047*
H24A	0.4027	0.8393	0.2698	0.064*
H24B	0.4052	0.6329	0.2709	0.064*
H24C	0.5023	0.7397	0.2662	0.064*
H26A	0.9133	0.3704	0.8023	0.064*
H26B	0.8531	0.4606	0.7556	0.064*
H26C	0.9138	0.5760	0.7964	0.064*
H27A	1.2072	0.5757	0.7367	0.064*
H27B	1.1440	0.4941	0.6897	0.064*
H27C	1.1992	0.3706	0.7307	0.064*
H28A	1.1483	0.4189	0.8307	0.067*
H28B	1.0414	0.4847	0.8387	0.067*
H28C	1.1240	0.6199	0.8254	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0241 (3)	0.0390 (5)	0.0309 (3)	0.0085 (2)	0.0024 (2)	−0.0075 (2)
Cl2	0.0239 (3)	0.0222 (4)	0.0281 (3)	0.0042 (2)	0.0049 (2)	−0.0001 (2)
S1	0.0298 (3)	0.0449 (5)	0.0273 (3)	0.0073 (3)	−0.0024 (2)	−0.0058 (2)
S2	0.0284 (3)	0.0327 (4)	0.0267 (3)	0.0031 (2)	−0.0006 (2)	−0.0030 (2)
O1	0.0391 (11)	0.0425 (14)	0.0201 (9)	0.0076 (9)	−0.0037 (7)	−0.0014 (8)
O2	0.0523 (14)	0.088 (2)	0.0243 (10)	−0.0060 (13)	−0.0066 (9)	−0.0075 (11)
N1	0.0212 (10)	0.0268 (14)	0.0192 (10)	0.0039 (9)	−0.0015 (8)	−0.0013 (8)
N2	0.0203 (10)	0.0235 (14)	0.0181 (9)	0.0022 (8)	−0.0007 (7)	−0.0002 (8)
N3	0.0329 (12)	0.0373 (16)	0.0229 (11)	−0.0012 (10)	−0.0016 (9)	0.0033 (10)
N4	0.0428 (15)	0.065 (2)	0.0292 (13)	0.0044 (14)	−0.0064 (11)	−0.0056 (12)
C1	0.0249 (12)	0.0191 (16)	0.0240 (12)	−0.0006 (10)	0.0013 (9)	−0.0014 (10)
C2	0.0204 (12)	0.0229 (17)	0.0279 (13)	0.0022 (10)	0.0031 (9)	−0.0033 (10)
C3	0.0237 (13)	0.0273 (18)	0.0313 (14)	0.0054 (11)	−0.0037 (10)	−0.0015 (11)
C4	0.0266 (13)	0.0288 (18)	0.0219 (12)	0.0061 (11)	−0.0023 (10)	−0.0005 (10)
C5	0.0216 (12)	0.0185 (16)	0.0250 (12)	−0.0014 (10)	0.0004 (9)	−0.0002 (10)
C6	0.0209 (11)	0.0165 (15)	0.0222 (11)	−0.0011 (10)	−0.0006 (9)	0.0009 (10)
C7	0.0243 (12)	0.0162 (15)	0.0188 (11)	−0.0008 (10)	−0.0012 (9)	0.0002 (9)
C8	0.0205 (11)	0.0143 (15)	0.0195 (11)	−0.0025 (10)	0.0016 (9)	−0.0006 (9)
C9	0.0232 (12)	0.0131 (15)	0.0227 (12)	−0.0040 (10)	0.0007 (9)	0.0024 (9)
C10	0.0209 (12)	0.0169 (16)	0.0229 (12)	−0.0014 (10)	0.0017 (9)	0.0015 (10)
C11	0.0233 (12)	0.0179 (16)	0.0220 (12)	−0.0021 (10)	0.0022 (9)	0.0010 (10)
C12	0.0209 (11)	0.0145 (16)	0.0272 (12)	0.0014 (10)	0.0062 (9)	0.0004 (10)
C13	0.0209 (12)	0.0216 (16)	0.0278 (13)	0.0029 (10)	−0.0019 (9)	0.0033 (10)
C14	0.0263 (13)	0.0206 (16)	0.0226 (12)	0.0011 (10)	−0.0010 (10)	0.0028 (10)
C15	0.0219 (11)	0.0172 (16)	0.0214 (12)	−0.0011 (10)	−0.0001 (9)	0.0026 (10)
C16	0.0207 (11)	0.0159 (15)	0.0232 (12)	−0.0022 (10)	−0.0009 (9)	0.0041 (10)
C17	0.0239 (12)	0.0189 (16)	0.0189 (11)	−0.0013 (10)	0.0008 (9)	−0.0006 (9)
C18	0.0212 (11)	0.0181 (16)	0.0201 (11)	−0.0016 (10)	−0.0003 (9)	−0.0015 (9)
C19	0.0219 (12)	0.0193 (16)	0.0242 (12)	−0.0013 (10)	0.0000 (9)	−0.0001 (10)
C20	0.0220 (12)	0.0157 (15)	0.0227 (12)	−0.0012 (9)	−0.0002 (9)	0.0006 (9)
C21	0.0313 (13)	0.0182 (17)	0.0274 (13)	−0.0047 (11)	0.0017 (10)	−0.0007 (10)
C22	0.0455 (17)	0.028 (2)	0.0387 (16)	0.0032 (14)	0.0123 (13)	−0.0028 (13)
C23	0.0306 (15)	0.036 (2)	0.0516 (18)	0.0039 (13)	0.0068 (13)	0.0109 (14)
C24	0.062 (2)	0.074 (2)	0.0252 (15)	−0.0022 (19)	−0.0084 (14)	0.0098 (16)
C25	0.0491 (18)	0.045 (2)	0.0318 (16)	−0.0008 (15)	−0.0052 (13)	0.0005 (14)
C26	0.0413 (18)	0.073 (3)	0.0451 (19)	0.0011 (18)	0.0038 (15)	0.0026 (18)
C27	0.0408 (19)	0.070 (2)	0.0485 (19)	0.0037 (17)	0.0081 (15)	0.0011 (17)
C28	0.056 (2)	0.083 (3)	0.0299 (16)	0.015 (2)	−0.0138 (15)	−0.0127 (17)

Geometric parameters (Å, º)

Cl1—C2	1.748 (3)	C10—C15	1.409 (3)
Cl2—C12	1.744 (3)	C10—C11	1.413 (4)
S1—C19	1.674 (3)	C11—C12	1.366 (3)
S2—C9	1.666 (2)	C11—H11	0.9500
O1—C21	1.236 (3)	C12—C13	1.407 (4)
O2—C25	1.234 (4)	C13—C14	1.360 (4)
N1—C5	1.354 (3)	C13—H13	0.9500
N1—C6	1.371 (3)	C14—C15	1.415 (3)
N1—H1N	0.8800	C14—H14	0.9500
N2—C15	1.353 (3)	C16—C17	1.390 (4)
N2—C16	1.371 (3)	C17—C18	1.392 (3)
N2—H2N	0.8800	C17—H17	0.9500
N3—C21	1.337 (4)	C18—C19	1.455 (3)
N3—C23	1.453 (4)	C19—C20	1.452 (3)
N3—C24	1.459 (4)	C21—C22	1.503 (4)
N4—C25	1.317 (4)	C22—H22A	0.9800
N4—C27	1.465 (4)	C22—H22B	0.9800
N4—C28	1.465 (4)	C22—H22C	0.9800
C1—C2	1.365 (4)	C23—H23A	0.9800
C1—C20	1.418 (4)	C23—H23B	0.9800
C1—H1	0.9500	C23—H23C	0.9800
C2—C3	1.403 (4)	C24—H24A	0.9800
C3—C4	1.363 (4)	C24—H24B	0.9800
C3—H3	0.9500	C24—H24C	0.9800
C4—C5	1.416 (4)	C25—C26	1.514 (5)
C4—H4	0.9500	C26—H26A	0.9800
C5—C20	1.412 (3)	C26—H26B	0.9800
C6—C7	1.394 (3)	C26—H26C	0.9800
C6—C18	1.425 (3)	C27—H27A	0.9800
C7—C8	1.391 (3)	C27—H27B	0.9800
C7—H7	0.9500	C27—H27C	0.9800
C8—C16	1.423 (3)	C28—H28A	0.9800
C8—C9	1.463 (3)	C28—H28B	0.9800
C9—C10	1.461 (3)	C28—H28C	0.9800
C5—N1—C6	122.5 (2)	N2—C16—C17	119.3 (2)
C5—N1—H1N	118.7	N2—C16—C8	119.6 (2)
C6—N1—H1N	118.7	C17—C16—C8	121.1 (2)
C15—N2—C16	122.7 (2)	C16—C17—C18	121.2 (2)
C15—N2—H2N	118.6	C16—C17—H17	119.4
C16—N2—H2N	118.6	C18—C17—H17	119.4
C21—N3—C23	120.4 (2)	C17—C18—C6	117.8 (2)
C21—N3—C24	123.3 (3)	C17—C18—C19	121.7 (2)
C23—N3—C24	115.9 (3)	C6—C18—C19	120.4 (2)
C25—N4—C27	118.7 (3)	C20—C19—C18	116.0 (2)
C25—N4—C28	124.6 (3)	C20—C19—S1	122.18 (19)
C27—N4—C28	116.6 (3)	C18—C19—S1	121.83 (19)
C2—C1—C20	120.3 (2)	C5—C20—C1	118.1 (2)
C2—C1—H1	119.9	C5—C20—C19	120.5 (2)
C20—C1—H1	119.9	C1—C20—C19	121.3 (2)
C1—C2—C3	121.4 (2)	O1—C21—N3	120.6 (2)
C1—C2—Cl1	119.6 (2)	O1—C21—C22	120.8 (3)
C3—C2—Cl1	118.96 (19)	N3—C21—C22	118.6 (2)
C4—C3—C2	119.8 (2)	C21—C22—H22A	109.5
C4—C3—H3	120.1	C21—C22—H22B	109.5
C2—C3—H3	120.1	H22A—C22—H22B	109.5
C3—C4—C5	120.2 (2)	C21—C22—H22C	109.5
C3—C4—H4	119.9	H22A—C22—H22C	109.5
C5—C4—H4	119.9	H22B—C22—H22C	109.5
N1—C5—C20	120.8 (2)	N3—C23—H23A	109.5
N1—C5—C4	119.0 (2)	N3—C23—H23B	109.5
C20—C5—C4	120.2 (2)	H23A—C23—H23B	109.5
N1—C6—C7	119.4 (2)	N3—C23—H23C	109.5
N1—C6—C18	119.7 (2)	H23A—C23—H23C	109.5
C7—C6—C18	120.8 (2)	H23B—C23—H23C	109.5
C8—C7—C6	121.2 (2)	N3—C24—H24A	109.5
C8—C7—H7	119.4	N3—C24—H24B	109.5
C6—C7—H7	119.4	H24A—C24—H24B	109.5
C7—C8—C16	117.8 (2)	N3—C24—H24C	109.5
C7—C8—C9	121.7 (2)	H24A—C24—H24C	109.5
C16—C8—C9	120.5 (2)	H24B—C24—H24C	109.5
C10—C9—C8	115.9 (2)	O2—C25—N4	121.7 (3)
C10—C9—S2	122.15 (19)	O2—C25—C26	120.6 (3)
C8—C9—S2	121.94 (18)	N4—C25—C26	117.6 (3)
C15—C10—C11	118.4 (2)	C25—C26—H26A	109.5
C15—C10—C9	120.1 (2)	C25—C26—H26B	109.5
C11—C10—C9	121.5 (2)	H26A—C26—H26B	109.5
C12—C11—C10	120.2 (2)	C25—C26—H26C	109.5
C12—C11—H11	119.9	H26A—C26—H26C	109.5
C10—C11—H11	119.9	H26B—C26—H26C	109.5
C11—C12—C13	121.3 (2)	N4—C27—H27A	109.5
C11—C12—Cl2	120.3 (2)	N4—C27—H27B	109.5
C13—C12—Cl2	118.47 (19)	H27A—C27—H27B	109.5
C14—C13—C12	119.8 (2)	N4—C27—H27C	109.5
C14—C13—H13	120.1	H27A—C27—H27C	109.5
C12—C13—H13	120.1	H27B—C27—H27C	109.5
C13—C14—C15	120.2 (2)	N4—C28—H28A	109.5
C13—C14—H14	119.9	N4—C28—H28B	109.5
C15—C14—H14	119.9	H28A—C28—H28B	109.5
N2—C15—C10	121.2 (2)	N4—C28—H28C	109.5
N2—C15—C14	118.7 (2)	H28A—C28—H28C	109.5
C10—C15—C14	120.1 (2)	H28B—C28—H28C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.88	1.89	2.747 (3)	164
N2—H2N···O2	0.88	1.89	2.772 (3)	176