5,12-Dihydro­quino[2,3-b]acridine-7,14-dithione dimethyl­acetamide disolvate

The title compound, C₂₀H₁₂N₂S₂·2C₄H₉NO, is a solvated centrosymmetric pigment mol­ecule (DTQ) connected to two dimethyl­acetamide (DMA) mol­ecules through N—H...O hydrogen bonds. One DTQ mol­ecule is surrounded by six DMA mol­ecules in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.072
• wR factor = 0.202
• 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 .......       0.93

Author Response: A two-dmensional detector (IP) was used in combination with Cu as radiation.

Alert level B
DIFMX01_ALERT_2_B  The maximum difference density is > 0.1*ZMAX*1.00
            _refine_diff_density_max given =      2.030
            Test value =      1.600
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............       2.03 e/A   

Alert level C
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           68.08
           From the CIF: _diffrn_reflns_theta_full          68.08
           From the CIF: _reflns_number_total               2166
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2319
           Completeness (_total/calc)             93.40%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.93
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.22
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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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: SHELXS86 (Sheldrick, 1985); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

5,12-Dihydroquino[2,3-b]acridine-7,14-dithione dimethylacetamide disolvate

Crystal data

C20H12N2S2·2C4H9NO	Z = 1
Mr = 518.70	F(000) = 274.00
Triclinic, P1	Dx = 1.353 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 7.353 (2) Å	Cell parameters from 5169 reflections
b = 8.328 (2) Å	θ = 4.0–68.0°
c = 11.832 (3) Å	µ = 2.17 mm^−1
α = 97.706 (17)°	T = 93 K
β = 105.859 (17)°	Prism, dark green
γ = 109.493 (17)°	0.20 × 0.15 × 0.10 mm
V = 636.4 (3) Å^3

Data collection

Rigaku R-AXIS RAPID-F Imaging Plate diffractometer	1941 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.051
ω scans	θmax = 68.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→8
Tmin = 0.632, Tmax = 0.805	k = −9→10
5445 measured reflections	l = −13→13
2166 independent reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.072	w = 1/[σ^2(Fo^2) + (0.1062P)^2 + 1.0872P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.202	(Δ/σ)max < 0.001
S = 1.13	Δρmax = 2.03 e Å^−3
2166 reflections	Δρmin = −0.63 e Å^−3
171 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	1.35485 (13)	1.14118 (11)	1.35057 (7)	0.0296 (3)
O1	0.5636 (4)	0.3923 (4)	0.8772 (2)	0.0461 (8)
N1	0.8905 (5)	0.6719 (4)	1.0478 (3)	0.0251 (7)
N2	0.3529 (6)	0.1207 (5)	0.7571 (3)	0.0499 (10)
C1	1.2201 (6)	0.7488 (5)	1.3623 (3)	0.0287 (8)
H1	1.3209	0.8423	1.4284	0.034*
C2	1.1640 (6)	0.5803 (5)	1.3752 (3)	0.0337 (9)
H2	1.2262	0.5576	1.4497	0.040*
C3	1.0135 (6)	0.4394 (5)	1.2778 (3)	0.0342 (9)
H3	0.9761	0.3225	1.2872	0.041*
C4	0.9213 (6)	0.4696 (4)	1.1704 (3)	0.0308 (8)
H4	0.8188	0.3745	1.1059	0.037*
C5	0.9798 (5)	0.6440 (4)	1.1556 (3)	0.0257 (7)
C6	1.1306 (5)	0.7868 (4)	1.2523 (3)	0.0251 (7)
C7	1.1898 (5)	0.9643 (4)	1.2374 (3)	0.0239 (7)
C8	1.0962 (5)	0.9847 (4)	1.1169 (3)	0.0232 (7)
C9	0.9451 (5)	0.8342 (4)	1.0244 (3)	0.0232 (7)
C10	1.1475 (5)	1.1482 (4)	1.0897 (3)	0.0238 (7)
H10	1.2476	1.2494	1.1503	0.029*
C11	0.4385 (7)	0.2909 (6)	0.7814 (5)	0.0533 (13)
C12	0.3636 (7)	0.3719 (5)	0.6691 (4)	0.0455 (11)
H12A	0.4007	0.3281	0.6012	0.055*
H12B	0.4303	0.5005	0.6944	0.055*
H12C	0.2144	0.3363	0.6436	0.055*
C13	0.2104 (6)	0.0081 (5)	0.6391 (3)	0.0353 (9)
H13A	0.2376	−0.0986	0.6228	0.042*
H13B	0.2285	0.0712	0.5761	0.042*
H13C	0.0694	−0.0240	0.6389	0.042*
C14	0.4049 (7)	0.0455 (7)	0.8601 (4)	0.0518 (12)
H14A	0.4601	−0.0419	0.8393	0.062*
H14B	0.2814	−0.0110	0.8799	0.062*
H14C	0.5080	0.1391	0.9304	0.062*
H1N	0.800 (6)	0.595 (6)	0.998 (4)	0.028 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0293 (6)	0.0275 (5)	0.0207 (5)	0.0049 (4)	0.0009 (3)	0.0019 (3)
O1	0.0359 (16)	0.0415 (16)	0.0336 (15)	−0.0031 (12)	0.0024 (12)	−0.0099 (12)
N1	0.0252 (17)	0.0200 (14)	0.0210 (14)	0.0041 (12)	0.0023 (12)	0.0002 (11)
N2	0.044 (2)	0.049 (2)	0.041 (2)	0.0076 (17)	0.0084 (17)	0.0003 (16)
C1	0.028 (2)	0.0302 (18)	0.0244 (17)	0.0102 (15)	0.0065 (14)	0.0047 (14)
C2	0.036 (2)	0.034 (2)	0.0291 (19)	0.0142 (16)	0.0058 (16)	0.0105 (15)
C3	0.040 (2)	0.0281 (19)	0.035 (2)	0.0137 (16)	0.0119 (17)	0.0109 (15)
C4	0.035 (2)	0.0204 (17)	0.0314 (18)	0.0062 (14)	0.0092 (15)	0.0036 (13)
C5	0.0255 (19)	0.0261 (17)	0.0245 (17)	0.0100 (14)	0.0081 (14)	0.0042 (13)
C6	0.0236 (19)	0.0260 (17)	0.0233 (17)	0.0086 (14)	0.0074 (14)	0.0025 (13)
C7	0.0198 (18)	0.0278 (18)	0.0210 (16)	0.0076 (14)	0.0058 (13)	0.0025 (13)
C8	0.0217 (18)	0.0249 (17)	0.0196 (15)	0.0074 (13)	0.0060 (13)	0.0017 (12)
C9	0.0207 (18)	0.0226 (16)	0.0236 (16)	0.0070 (13)	0.0072 (13)	0.0015 (13)
C10	0.0204 (18)	0.0214 (16)	0.0240 (16)	0.0053 (13)	0.0056 (13)	−0.0001 (12)
C11	0.031 (2)	0.041 (2)	0.074 (3)	0.0029 (19)	0.024 (2)	−0.015 (2)
C12	0.053 (3)	0.030 (2)	0.062 (3)	0.0155 (19)	0.031 (2)	0.0154 (19)
C13	0.027 (2)	0.038 (2)	0.0269 (18)	0.0044 (16)	0.0040 (15)	−0.0040 (15)
C14	0.046 (3)	0.085 (3)	0.037 (2)	0.032 (2)	0.018 (2)	0.030 (2)

Geometric parameters (Å, º)

S1—C7	1.681 (3)	C6—C7	1.444 (5)
O1—C11	1.224 (5)	C7—C8	1.464 (5)
N1—C5	1.354 (4)	C8—C10	1.394 (5)
N1—C9	1.366 (4)	C8—C9	1.429 (5)
N1—H1N	0.77 (4)	C9—C10^i	1.387 (5)
N2—C11	1.298 (6)	C10—C9^i	1.387 (5)
N2—C13	1.456 (5)	C10—H10	0.9500
N2—C14	1.461 (6)	C11—C12	1.617 (7)
C1—C2	1.367 (5)	C12—H12A	0.9800
C1—C6	1.418 (5)	C12—H12B	0.9800
C1—H1	0.9500	C12—H12C	0.9800
C2—C3	1.416 (5)	C13—H13A	0.9800
C2—H2	0.9500	C13—H13B	0.9800
C3—C4	1.366 (5)	C13—H13C	0.9800
C3—H3	0.9500	C14—H14A	0.9800
C4—C5	1.421 (5)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—C6	1.419 (5)
C5—N1—C9	122.7 (3)	C9—C8—C7	119.6 (3)
C5—N1—H1N	120 (3)	N1—C9—C10^i	119.5 (3)
C9—N1—H1N	117 (3)	N1—C9—C8	120.2 (3)
C11—N2—C13	124.6 (4)	C10^i—C9—C8	120.3 (3)
C11—N2—C14	114.7 (4)	C9^i—C10—C8	121.2 (3)
C13—N2—C14	120.7 (4)	C9^i—C10—H10	119.4
C2—C1—C6	121.3 (3)	C8—C10—H10	119.4
C2—C1—H1	119.3	O1—C11—N2	127.8 (5)
C6—C1—H1	119.3	O1—C11—C12	118.4 (4)
C1—C2—C3	120.1 (3)	N2—C11—C12	113.7 (4)
C1—C2—H2	120.0	C11—C12—H12A	109.5
C3—C2—H2	120.0	C11—C12—H12B	109.5
C4—C3—C2	120.8 (3)	H12A—C12—H12B	109.5
C4—C3—H3	119.6	C11—C12—H12C	109.5
C2—C3—H3	119.6	H12A—C12—H12C	109.5
C3—C4—C5	119.6 (3)	H12B—C12—H12C	109.5
C3—C4—H4	120.2	N2—C13—H13A	109.5
C5—C4—H4	120.2	N2—C13—H13B	109.5
N1—C5—C6	120.5 (3)	H13A—C13—H13B	109.5
N1—C5—C4	119.1 (3)	N2—C13—H13C	109.5
C6—C5—C4	120.4 (3)	H13A—C13—H13C	109.5
C1—C6—C5	117.8 (3)	H13B—C13—H13C	109.5
C1—C6—C7	121.7 (3)	N2—C14—H14A	109.5
C5—C6—C7	120.4 (3)	N2—C14—H14B	109.5
C6—C7—C8	116.4 (3)	H14A—C14—H14B	109.5
C6—C7—S1	123.1 (3)	N2—C14—H14C	109.5
C8—C7—S1	120.5 (3)	H14A—C14—H14C	109.5
C10—C8—C9	118.5 (3)	H14B—C14—H14C	109.5
C10—C8—C7	121.9 (3)

Symmetry code: (i) −x+2, −y+2, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.77 (4)	1.99 (4)	2.762 (4)	177 (4)