The title compound, C
20H
12N
2S
2·2C
4H
9NO, 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.
Supporting information
CCDC reference: 624945
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (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
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
top
Crystal data top
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) Å3 | |
Data collection top
Rigaku R-AXIS RAPID-F Imaging Plate diffractometer | 1941 reflections with F2 > 2σ(F2) |
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 top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.072 | w = 1/[σ2(Fo2) + (0.1062P)2 + 1.0872P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C10i | 1.387 (5) |
N2—C11 | 1.298 (6) | C10—C9i | 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—C10i | 119.5 (3) |
C9—N1—H1N | 117 (3) | N1—C9—C8 | 120.2 (3) |
C11—N2—C13 | 124.6 (4) | C10i—C9—C8 | 120.3 (3) |
C11—N2—C14 | 114.7 (4) | C9i—C10—C8 | 121.2 (3) |
C13—N2—C14 | 120.7 (4) | C9i—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) top
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) |