Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806034350/ob2058sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806034350/ob2058Isup2.hkl
Contains datablock I

CCDC reference: 624945

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

Computing details top

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
C20H12N2S2·2C4H9NOZ = 1
Mr = 518.70F(000) = 274.00
Triclinic, P1Dx = 1.353 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.5418 Å
a = 7.353 (2) ÅCell parameters from 5169 reflections
b = 8.328 (2) Åθ = 4.0–68.0°
c = 11.832 (3) ŵ = 2.17 mm1
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-1Rint = 0.051
ω scansθmax = 68.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 78
Tmin = 0.632, Tmax = 0.805k = 910
5445 measured reflectionsl = 1313
2166 independent reflections
Refinement top
Refinement on F2H 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 = 1.13Δρmax = 2.03 e Å3
2166 reflectionsΔρmin = 0.63 e Å3
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
xyzUiso*/Ueq
S11.35485 (13)1.14118 (11)1.35057 (7)0.0296 (3)
O10.5636 (4)0.3923 (4)0.8772 (2)0.0461 (8)
N10.8905 (5)0.6719 (4)1.0478 (3)0.0251 (7)
N20.3529 (6)0.1207 (5)0.7571 (3)0.0499 (10)
C11.2201 (6)0.7488 (5)1.3623 (3)0.0287 (8)
H11.32090.84231.42840.034*
C21.1640 (6)0.5803 (5)1.3752 (3)0.0337 (9)
H21.22620.55761.44970.040*
C31.0135 (6)0.4394 (5)1.2778 (3)0.0342 (9)
H30.97610.32251.28720.041*
C40.9213 (6)0.4696 (4)1.1704 (3)0.0308 (8)
H40.81880.37451.10590.037*
C50.9798 (5)0.6440 (4)1.1556 (3)0.0257 (7)
C61.1306 (5)0.7868 (4)1.2523 (3)0.0251 (7)
C71.1898 (5)0.9643 (4)1.2374 (3)0.0239 (7)
C81.0962 (5)0.9847 (4)1.1169 (3)0.0232 (7)
C90.9451 (5)0.8342 (4)1.0244 (3)0.0232 (7)
C101.1475 (5)1.1482 (4)1.0897 (3)0.0238 (7)
H101.24761.24941.15030.029*
C110.4385 (7)0.2909 (6)0.7814 (5)0.0533 (13)
C120.3636 (7)0.3719 (5)0.6691 (4)0.0455 (11)
H12A0.40070.32810.60120.055*
H12B0.43030.50050.69440.055*
H12C0.21440.33630.64360.055*
C130.2104 (6)0.0081 (5)0.6391 (3)0.0353 (9)
H13A0.23760.09860.62280.042*
H13B0.22850.07120.57610.042*
H13C0.06940.02400.63890.042*
C140.4049 (7)0.0455 (7)0.8601 (4)0.0518 (12)
H14A0.46010.04190.83930.062*
H14B0.28140.01100.87990.062*
H14C0.50800.13910.93040.062*
H1N0.800 (6)0.595 (6)0.998 (4)0.028 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0293 (6)0.0275 (5)0.0207 (5)0.0049 (4)0.0009 (3)0.0019 (3)
O10.0359 (16)0.0415 (16)0.0336 (15)0.0031 (12)0.0024 (12)0.0099 (12)
N10.0252 (17)0.0200 (14)0.0210 (14)0.0041 (12)0.0023 (12)0.0002 (11)
N20.044 (2)0.049 (2)0.041 (2)0.0076 (17)0.0084 (17)0.0003 (16)
C10.028 (2)0.0302 (18)0.0244 (17)0.0102 (15)0.0065 (14)0.0047 (14)
C20.036 (2)0.034 (2)0.0291 (19)0.0142 (16)0.0058 (16)0.0105 (15)
C30.040 (2)0.0281 (19)0.035 (2)0.0137 (16)0.0119 (17)0.0109 (15)
C40.035 (2)0.0204 (17)0.0314 (18)0.0062 (14)0.0092 (15)0.0036 (13)
C50.0255 (19)0.0261 (17)0.0245 (17)0.0100 (14)0.0081 (14)0.0042 (13)
C60.0236 (19)0.0260 (17)0.0233 (17)0.0086 (14)0.0074 (14)0.0025 (13)
C70.0198 (18)0.0278 (18)0.0210 (16)0.0076 (14)0.0058 (13)0.0025 (13)
C80.0217 (18)0.0249 (17)0.0196 (15)0.0074 (13)0.0060 (13)0.0017 (12)
C90.0207 (18)0.0226 (16)0.0236 (16)0.0070 (13)0.0072 (13)0.0015 (13)
C100.0204 (18)0.0214 (16)0.0240 (16)0.0053 (13)0.0056 (13)0.0001 (12)
C110.031 (2)0.041 (2)0.074 (3)0.0029 (19)0.024 (2)0.015 (2)
C120.053 (3)0.030 (2)0.062 (3)0.0155 (19)0.031 (2)0.0154 (19)
C130.027 (2)0.038 (2)0.0269 (18)0.0044 (16)0.0040 (15)0.0040 (15)
C140.046 (3)0.085 (3)0.037 (2)0.032 (2)0.018 (2)0.030 (2)
Geometric parameters (Å, º) top
S1—C71.681 (3)C6—C71.444 (5)
O1—C111.224 (5)C7—C81.464 (5)
N1—C51.354 (4)C8—C101.394 (5)
N1—C91.366 (4)C8—C91.429 (5)
N1—H1N0.77 (4)C9—C10i1.387 (5)
N2—C111.298 (6)C10—C9i1.387 (5)
N2—C131.456 (5)C10—H100.9500
N2—C141.461 (6)C11—C121.617 (7)
C1—C21.367 (5)C12—H12A0.9800
C1—C61.418 (5)C12—H12B0.9800
C1—H10.9500C12—H12C0.9800
C2—C31.416 (5)C13—H13A0.9800
C2—H20.9500C13—H13B0.9800
C3—C41.366 (5)C13—H13C0.9800
C3—H30.9500C14—H14A0.9800
C4—C51.421 (5)C14—H14B0.9800
C4—H40.9500C14—H14C0.9800
C5—C61.419 (5)
C5—N1—C9122.7 (3)C9—C8—C7119.6 (3)
C5—N1—H1N120 (3)N1—C9—C10i119.5 (3)
C9—N1—H1N117 (3)N1—C9—C8120.2 (3)
C11—N2—C13124.6 (4)C10i—C9—C8120.3 (3)
C11—N2—C14114.7 (4)C9i—C10—C8121.2 (3)
C13—N2—C14120.7 (4)C9i—C10—H10119.4
C2—C1—C6121.3 (3)C8—C10—H10119.4
C2—C1—H1119.3O1—C11—N2127.8 (5)
C6—C1—H1119.3O1—C11—C12118.4 (4)
C1—C2—C3120.1 (3)N2—C11—C12113.7 (4)
C1—C2—H2120.0C11—C12—H12A109.5
C3—C2—H2120.0C11—C12—H12B109.5
C4—C3—C2120.8 (3)H12A—C12—H12B109.5
C4—C3—H3119.6C11—C12—H12C109.5
C2—C3—H3119.6H12A—C12—H12C109.5
C3—C4—C5119.6 (3)H12B—C12—H12C109.5
C3—C4—H4120.2N2—C13—H13A109.5
C5—C4—H4120.2N2—C13—H13B109.5
N1—C5—C6120.5 (3)H13A—C13—H13B109.5
N1—C5—C4119.1 (3)N2—C13—H13C109.5
C6—C5—C4120.4 (3)H13A—C13—H13C109.5
C1—C6—C5117.8 (3)H13B—C13—H13C109.5
C1—C6—C7121.7 (3)N2—C14—H14A109.5
C5—C6—C7120.4 (3)N2—C14—H14B109.5
C6—C7—C8116.4 (3)H14A—C14—H14B109.5
C6—C7—S1123.1 (3)N2—C14—H14C109.5
C8—C7—S1120.5 (3)H14A—C14—H14C109.5
C10—C8—C9118.5 (3)H14B—C14—H14C109.5
C10—C8—C7121.9 (3)
Symmetry code: (i) x+2, y+2, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O10.77 (4)1.99 (4)2.762 (4)177 (4)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds