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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007634/ob6489sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007634/ob6489Isup2.hkl
Contains datablock I

CCDC reference: 270501

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](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

Computing details top

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
C20H10Cl2N2O2F(000) = 388.00
Mr = 381.20Dx = 1.744 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 4881 reflections
a = 3.782 (1) Åθ = 3.0–68.1°
b = 14.840 (4) ŵ = 4.20 mm1
c = 12.942 (3) ÅT = 93 K
β = 91.93 (2)°Needle, black
V = 726.0 (3) Å30.40 × 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-1Rint = 0.078
ω scansθmax = 68.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 33
Tmin = 0.677, Tmax = 0.919k = 1717
6026 measured reflectionsl = 1515
1222 independent reflections
Refinement top
Refinement on F2H-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 = 1.14Δρmax = 0.56 e Å3
1222 reflectionsΔρmin = 0.93 e Å3
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
xyzUiso*/Ueq
Cl10.2925 (8)0.4666 (2)0.6599 (2)0.045 (1)
O10.908 (2)0.1444 (4)0.7335 (4)0.018 (2)
N10.638 (2)0.1441 (5)0.4199 (5)0.020 (2)
C10.573 (2)0.3006 (6)0.6447 (6)0.018 (2)
C20.401 (2)0.3720 (6)0.5953 (7)0.018 (2)
C30.308 (2)0.3678 (6)0.4899 (7)0.021 (2)
C40.382 (2)0.2901 (6)0.4343 (6)0.017 (2)
C50.559 (2)0.2181 (6)0.4814 (6)0.016 (2)
C60.653 (2)0.2233 (6)0.5898 (6)0.016 (2)
C70.833 (2)0.1454 (6)0.6395 (6)0.018 (2)
C80.927 (2)0.0718 (6)0.5700 (6)0.017 (2)
C90.805 (2)0.0760 (6)0.4608 (6)0.016 (2)
C101.108 (2)0.0018 (6)0.6047 (6)0.017 (2)
H10.63440.30460.71480.022*
H1N0.57550.14370.35530.024*
H30.19630.41640.45720.026*
H40.31310.28640.36480.020*
H101.17930.00430.67420.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.049 (2)0.045 (2)0.039 (2)0.002 (1)0.002 (1)0.001 (1)
O10.017 (4)0.029 (3)0.008 (3)0.002 (3)0.005 (2)0.001 (2)
N10.020 (5)0.030 (4)0.010 (3)0.002 (3)0.001 (3)0.001 (3)
C10.007 (6)0.032 (5)0.016 (4)0.004 (4)0.005 (3)0.000 (3)
C20.011 (5)0.022 (4)0.022 (4)0.001 (4)0.005 (3)0.001 (4)
C30.009 (6)0.025 (5)0.030 (5)0.002 (4)0.004 (4)0.005 (4)
C40.009 (5)0.027 (5)0.015 (4)0.002 (4)0.004 (3)0.003 (3)
C50.008 (6)0.023 (4)0.017 (4)0.004 (4)0.004 (3)0.004 (3)
C60.005 (5)0.028 (5)0.014 (4)0.002 (4)0.001 (3)0.005 (3)
C70.009 (6)0.023 (5)0.022 (4)0.004 (4)0.005 (3)0.001 (4)
C80.018 (6)0.020 (4)0.013 (4)0.006 (4)0.002 (4)0.002 (3)
C90.010 (6)0.026 (5)0.011 (4)0.001 (4)0.001 (3)0.004 (3)
C100.013 (5)0.028 (5)0.010 (3)0.003 (4)0.003 (3)0.001 (3)
Geometric parameters (Å, º) top
Cl1—C21.691 (9)C4—C51.39 (1)
O1—C71.24 (1)C4—H40.9300
N1—C51.39 (1)C5—C61.44 (1)
N1—C91.30 (1)C6—C71.48 (1)
N1—H1N0.8601C7—C81.47 (1)
C1—C21.39 (1)C8—C91.47 (1)
C1—C61.39 (1)C8—C101.36 (1)
C1—H10.9300C9—C10i1.43 (1)
C2—C31.40 (1)C10—C9i1.43 (1)
C3—C41.39 (1)C10—H100.9300
C3—H30.9300
Cl1···O1ii3.084 (6)H1···H1Niii1.994
Cl1—C2—C1121.5 (7)H3—C3—C4120.2440
Cl1—C2—C3117.6 (7)C3—C4—C5120.8 (8)
O1—C7—C6121.5 (8)C3—C4—H4119.5789
O1—C7—C8122.8 (8)C4—C5—C6119.0 (8)
N1—C5—C6123.4 (7)H4—C4—C5119.5922
N1—C5—C4117.6 (7)C5—C6—C7118.5 (7)
C9—N1—C5119.4 (7)C6—C7—C8115.7 (7)
H1N—N1—C5120.2990C7—C8—C10121.7 (7)
N1—C9—C8123.9 (7)C7—C8—C9118.9 (7)
N1—C9—C10i118.3 (7)C10—C8—C9119.3 (7)
H1N—N1—C9120.3002C8—C9—C10i117.7 (7)
C1—C2—C3120.9 (8)C8—C10—H10118.5189
H1—C1—C2119.9576C8—C10—C9i123.0 (7)
C6—C1—C2120.1 (8)C9—C10i—H10i118.5083
H1—C1—C6119.9639C9—C10i—C8i123.0 (7)
C1—C6—C7121.9 (7)H10—C10—C9i118.5083
C1—C6—C5119.6 (8)C10—C9i—C8i117.7 (7)
C2—C3—H3120.2419C10—C9i—N1i118.3 (7)
C2—C3—C4119.5 (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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