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The title compound, C20H10Cl2N2O2, is an industrially important red pigment. The molecule has inversion symmetry. The molecule is not entirely planar, as shown by the dihedral angle of 176.7 (3)° between the planes of the benzene ring at the center and that at the extremity. The molecules are stacked in a `hunter's fence' fashion (i.e. when viewed from the side, the molecules cross one another with an angle of about 50° in a grid-like structure) along the a axis.
Supporting information
CCDC reference: 270501
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (C-C) = 0.012 Å
- R factor = 0.100
- wR factor = 0.350
- Data-to-parameter ratio = 10.3
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91
| Author Response: A two-dimensional detector (IP) was used in combination with a Cu
target as radiation.
|
Alert level B
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 12
PLAT415_ALERT_2_B Short Inter D-H..H-X H1 .. H1N .. 1.99 Ang.
Alert level C
REFLT03_ALERT_3_C Reflection count < 95% complete
From the CIF: _diffrn_reflns_theta_max 68.23
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 1222
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 1334
Completeness (_total/calc) 91.60%
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.350
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92
PLAT084_ALERT_2_C High R2 Value .................................. 0.35
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03
PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1N ... ?
PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O1 .. 3.08 Ang.
1 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
5 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2004); 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.
2,9-Dichloro-5,12-dihydroquino[2,3-
b]acridine-7,14-dione
top
Crystal data top
C20H10Cl2N2O2 | F(000) = 388.00 |
Mr = 381.20 | Dx = 1.744 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 4881 reflections |
a = 3.782 (1) Å | θ = 3.0–68.1° |
b = 14.840 (4) Å | µ = 4.20 mm−1 |
c = 12.942 (3) Å | T = 93 K |
β = 91.93 (2)° | Needle, black |
V = 726.0 (3) Å3 | 0.40 × 0.05 × 0.02 mm |
Z = 2 | |
Data collection top
Rigaku R-AXIS RAPID imaging plate diffractometer | 745 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.078 |
ω scans | θmax = 68.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −3→3 |
Tmin = 0.677, Tmax = 0.919 | k = −17→17 |
6026 measured reflections | l = −15→15 |
1222 independent reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.100 | w = 1/[σ2(Fo2) + (0.1985P)2 + 2.3331P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.350 | (Δ/σ)max < 0.001 |
S = 1.14 | Δρmax = 0.56 e Å−3 |
1222 reflections | Δρmin = −0.93 e Å−3 |
119 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 | |
Cl1 | 0.2925 (8) | 0.4666 (2) | 0.6599 (2) | 0.045 (1) | |
O1 | 0.908 (2) | 0.1444 (4) | 0.7335 (4) | 0.018 (2) | |
N1 | 0.638 (2) | 0.1441 (5) | 0.4199 (5) | 0.020 (2) | |
C1 | 0.573 (2) | 0.3006 (6) | 0.6447 (6) | 0.018 (2) | |
C2 | 0.401 (2) | 0.3720 (6) | 0.5953 (7) | 0.018 (2) | |
C3 | 0.308 (2) | 0.3678 (6) | 0.4899 (7) | 0.021 (2) | |
C4 | 0.382 (2) | 0.2901 (6) | 0.4343 (6) | 0.017 (2) | |
C5 | 0.559 (2) | 0.2181 (6) | 0.4814 (6) | 0.016 (2) | |
C6 | 0.653 (2) | 0.2233 (6) | 0.5898 (6) | 0.016 (2) | |
C7 | 0.833 (2) | 0.1454 (6) | 0.6395 (6) | 0.018 (2) | |
C8 | 0.927 (2) | 0.0718 (6) | 0.5700 (6) | 0.017 (2) | |
C9 | 0.805 (2) | 0.0760 (6) | 0.4608 (6) | 0.016 (2) | |
C10 | 1.108 (2) | −0.0018 (6) | 0.6047 (6) | 0.017 (2) | |
H1 | 0.6344 | 0.3046 | 0.7148 | 0.022* | |
H1N | 0.5755 | 0.1437 | 0.3553 | 0.024* | |
H3 | 0.1963 | 0.4164 | 0.4572 | 0.026* | |
H4 | 0.3131 | 0.2864 | 0.3648 | 0.020* | |
H10 | 1.1793 | −0.0043 | 0.6742 | 0.020* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.049 (2) | 0.045 (2) | 0.039 (2) | 0.002 (1) | −0.002 (1) | −0.001 (1) |
O1 | 0.017 (4) | 0.029 (3) | 0.008 (3) | −0.002 (3) | −0.005 (2) | −0.001 (2) |
N1 | 0.020 (5) | 0.030 (4) | 0.010 (3) | −0.002 (3) | −0.001 (3) | 0.001 (3) |
C1 | 0.007 (6) | 0.032 (5) | 0.016 (4) | −0.004 (4) | 0.005 (3) | −0.000 (3) |
C2 | 0.011 (5) | 0.022 (4) | 0.022 (4) | −0.001 (4) | 0.005 (3) | −0.001 (4) |
C3 | 0.009 (6) | 0.025 (5) | 0.030 (5) | 0.002 (4) | 0.004 (4) | 0.005 (4) |
C4 | 0.009 (5) | 0.027 (5) | 0.015 (4) | 0.002 (4) | 0.004 (3) | 0.003 (3) |
C5 | 0.008 (6) | 0.023 (4) | 0.017 (4) | −0.004 (4) | 0.004 (3) | 0.004 (3) |
C6 | 0.005 (5) | 0.028 (5) | 0.014 (4) | −0.002 (4) | 0.001 (3) | 0.005 (3) |
C7 | 0.009 (6) | 0.023 (5) | 0.022 (4) | −0.004 (4) | 0.005 (3) | 0.001 (4) |
C8 | 0.018 (6) | 0.020 (4) | 0.013 (4) | −0.006 (4) | −0.002 (4) | −0.002 (3) |
C9 | 0.010 (6) | 0.026 (5) | 0.011 (4) | −0.001 (4) | 0.001 (3) | 0.004 (3) |
C10 | 0.013 (5) | 0.028 (5) | 0.010 (3) | −0.003 (4) | −0.003 (3) | 0.001 (3) |
Geometric parameters (Å, º) top
Cl1—C2 | 1.691 (9) | C4—C5 | 1.39 (1) |
O1—C7 | 1.24 (1) | C4—H4 | 0.9300 |
N1—C5 | 1.39 (1) | C5—C6 | 1.44 (1) |
N1—C9 | 1.30 (1) | C6—C7 | 1.48 (1) |
N1—H1N | 0.8601 | C7—C8 | 1.47 (1) |
C1—C2 | 1.39 (1) | C8—C9 | 1.47 (1) |
C1—C6 | 1.39 (1) | C8—C10 | 1.36 (1) |
C1—H1 | 0.9300 | C9—C10i | 1.43 (1) |
C2—C3 | 1.40 (1) | C10—C9i | 1.43 (1) |
C3—C4 | 1.39 (1) | C10—H10 | 0.9300 |
C3—H3 | 0.9300 | | |
| | | |
Cl1···O1ii | 3.084 (6) | H1···H1Niii | 1.994 |
| | | |
Cl1—C2—C1 | 121.5 (7) | H3—C3—C4 | 120.2440 |
Cl1—C2—C3 | 117.6 (7) | C3—C4—C5 | 120.8 (8) |
O1—C7—C6 | 121.5 (8) | C3—C4—H4 | 119.5789 |
O1—C7—C8 | 122.8 (8) | C4—C5—C6 | 119.0 (8) |
N1—C5—C6 | 123.4 (7) | H4—C4—C5 | 119.5922 |
N1—C5—C4 | 117.6 (7) | C5—C6—C7 | 118.5 (7) |
C9—N1—C5 | 119.4 (7) | C6—C7—C8 | 115.7 (7) |
H1N—N1—C5 | 120.2990 | C7—C8—C10 | 121.7 (7) |
N1—C9—C8 | 123.9 (7) | C7—C8—C9 | 118.9 (7) |
N1—C9—C10i | 118.3 (7) | C10—C8—C9 | 119.3 (7) |
H1N—N1—C9 | 120.3002 | C8—C9—C10i | 117.7 (7) |
C1—C2—C3 | 120.9 (8) | C8—C10—H10 | 118.5189 |
H1—C1—C2 | 119.9576 | C8—C10—C9i | 123.0 (7) |
C6—C1—C2 | 120.1 (8) | C9—C10i—H10i | 118.5083 |
H1—C1—C6 | 119.9639 | C9—C10i—C8i | 123.0 (7) |
C1—C6—C7 | 121.9 (7) | H10—C10—C9i | 118.5083 |
C1—C6—C5 | 119.6 (8) | C10—C9i—C8i | 117.7 (7) |
C2—C3—H3 | 120.2419 | C10—C9i—N1i | 118.3 (7) |
C2—C3—C4 | 119.5 (8) | | |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+1, y+1/2, −z+3/2; (iii) x, −y+1/2, z+1/2. |
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