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The title compound, C20H12N2O2, is a centrosymmetric pigment mol­ecule. The mol­ecules are doubly linked via N—H...O hydrogen bonds, forming ribbons along [110] and [1{\overline 1}0].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037524/ob2065sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037524/ob2065Isup2.hkl
Contains datablock I

CCDC reference: 624950

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.160
  • wR factor = 0.431
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level A DIFMX01_ALERT_2_A The maximum difference density is > 0.1*ZMAX*2.00 _refine_diff_density_max given = 2.400 Test value = 1.600 PLAT097_ALERT_2_A Maximum (Positive) Residual Density ............ 2.40 e/A   
Alert level B RFACG01_ALERT_3_B The value of the R factor is > 0.15 R factor given 0.160 RFACR01_ALERT_3_B The value of the weighted R factor is > 0.35 Weighted R factor given 0.431 PLAT082_ALERT_2_B High R1 Value .................................. 0.16 PLAT084_ALERT_2_B High R2 Value .................................. 0.43 PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 5.00
Alert level C DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.120 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C8 .. 6.34 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.01 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
2 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 8 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 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 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: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

5,7,12,14-Tetrahydro[2,3-b]quinolinoacridine (β form) top
Crystal data top
C20H12N2O2F(000) = 324.00
Mr = 312.32Dx = 1.566 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybcCell parameters from 4867 reflections
a = 5.7366 (6) Åθ = 3.0–68.3°
b = 3.8851 (4) ŵ = 0.83 mm1
c = 29.880 (4) ÅT = 296 K
β = 95.861 (8)°Platelet, red
V = 662.46 (13) Å30.42 × 0.20 × 0.04 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID
diffractometer
977 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.120
ω scansθmax = 68.3°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 66
Tmin = 0.705, Tmax = 0.965k = 44
5102 measured reflectionsl = 3535
1187 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.160 w = 1/[σ2(Fo2) + (0.1985P)2 + 9.1P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.431(Δ/σ)max < 0.001
S = 1.06Δρmax = 2.40 e Å3
1187 reflectionsΔρmin = 0.48 e Å3
110 parameters
Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F2 > 2 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.2937 (11)0.5833 (17)0.0891 (2)0.0443 (18)
N10.3029 (10)1.1530 (15)0.07695 (19)0.0234 (15)
C10.0030 (11)0.7669 (18)0.1684 (2)0.0207 (15)
C20.1495 (12)0.8383 (18)0.2046 (2)0.0234 (17)
C30.3608 (12)1.0140 (18)0.1990 (2)0.0233 (16)
C40.4094 (12)1.1109 (18)0.1571 (2)0.0213 (16)
C50.2531 (11)1.0417 (17)0.1193 (2)0.0204 (16)
C60.1526 (11)1.0778 (18)0.0388 (2)0.0213 (16)
C70.0550 (11)0.8919 (17)0.0422 (2)0.0190 (16)
C80.1149 (11)0.7700 (18)0.0858 (2)0.0181 (15)
C90.0444 (11)0.8615 (17)0.1246 (2)0.0200 (16)
C100.2085 (12)1.1838 (18)0.0036 (2)0.0202 (15)
H1N0.42831.26970.07440.028*
H10.14210.65320.17240.025*
H20.11600.77240.23320.028*
H30.46641.06320.22390.028*
H40.54901.22490.15370.026*
H100.34671.30400.00620.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.043 (3)0.045 (3)0.045 (3)0.003 (3)0.002 (2)0.002 (2)
N10.018 (3)0.018 (3)0.035 (3)0.000 (2)0.005 (2)0.000 (2)
C10.009 (3)0.020 (3)0.032 (3)0.003 (2)0.002 (2)0.002 (2)
C20.024 (4)0.022 (3)0.026 (3)0.006 (3)0.007 (2)0.002 (2)
C30.019 (3)0.023 (3)0.026 (3)0.002 (3)0.003 (2)0.001 (2)
C40.011 (3)0.018 (3)0.034 (3)0.002 (2)0.001 (2)0.002 (2)
C50.018 (3)0.014 (3)0.029 (3)0.006 (2)0.004 (2)0.000 (2)
C60.016 (3)0.017 (3)0.031 (3)0.007 (2)0.000 (2)0.002 (2)
C70.015 (3)0.016 (3)0.027 (3)0.008 (2)0.004 (2)0.001 (2)
C80.008 (3)0.019 (3)0.027 (3)0.004 (2)0.003 (2)0.000 (2)
C90.014 (3)0.014 (3)0.031 (3)0.001 (2)0.001 (2)0.002 (2)
C100.013 (3)0.017 (3)0.031 (3)0.002 (2)0.005 (2)0.002 (2)
Geometric parameters (Å, º) top
O1—C81.269 (9)C3—H30.930
N1—C51.394 (8)C4—C51.395 (9)
N1—C61.390 (8)C4—H40.930
N1—H1N0.860C5—C91.409 (9)
C1—C21.348 (9)C6—C71.406 (9)
C1—C91.415 (9)C6—C101.398 (9)
C1—H10.930C7—C81.459 (9)
C2—C31.416 (10)C7—C10i1.410 (9)
C2—H20.930C8—C91.444 (9)
C3—C41.363 (10)C10—H100.930
O1···H1Nii2.019H3···H3v2.497
H1N···O1iii2.019H4···H1iii2.454
H1···H4ii2.454H10···H10vi2.328
H3···H3iv2.497
C5—N1—C6120.8 (5)C4—C5—C9119.3 (6)
C5—N1—H1N119.6N1—C6—C7120.4 (6)
C6—N1—H1N119.6N1—C6—C10120.0 (6)
C2—C1—C9121.3 (6)C7—C6—C10119.5 (6)
C2—C1—H1119.3C6—C7—C8120.7 (5)
C9—C1—H1119.4C6—C7—C10i120.6 (6)
C1—C2—C3119.8 (6)C8—C7—C10i118.6 (6)
C1—C2—H2120.1O1—C8—C7121.4 (5)
C3—C2—H2120.1O1—C8—C9121.9 (6)
C2—C3—C4120.0 (6)C7—C8—C9116.6 (5)
C2—C3—H3120.0C1—C9—C5118.6 (5)
C4—C3—H3120.0C1—C9—C8120.9 (6)
C3—C4—C5121.0 (6)C5—C9—C8120.5 (6)
C3—C4—H4119.5C6—C10—C7i119.8 (6)
C5—C4—H4119.5C6—C10—H10120.1
N1—C5—C4120.0 (6)C7i—C10—H10120.1
N1—C5—C9120.7 (5)
Symmetry codes: (i) x, y+2, z; (ii) x1, y1, z; (iii) x+1, y+1, z; (iv) x+1, y1/2, z+1/2; (v) x+1, y+1/2, z+1/2; (vi) x+1, y+3, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1iii0.862.022.848 (8)161
Symmetry code: (iii) x+1, y+1, z.
 

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