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The title compound, C20H10Cl2N2O2, is one of the quinacridone derivatives known as a red pigment. The mol­ecule has inversion symmetry. The quinacridone molecules are connected by bifurcated N—H...O hydrogen bonds along [110] to form a two-dimensional hydrogen-bond network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022257/ob6549sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022257/ob6549Isup2.hkl
Contains datablock I

CCDC reference: 282570

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.056
  • wR factor = 0.178
  • Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.90
Author Response: A two-dmensional detector (IP) was used in combination with Cu as radiation.

Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 68.06 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 1217 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1346 Completeness (_total/calc) 90.42% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.90 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. Cl1 .. 3.28 Ang.
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 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 1 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

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, 1986); 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
C20H10Cl2N2O2Z = 1
Mr = 381.22F(000) = 194.00
Triclinic, P1Dx = 1.727 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.5418 Å
a = 3.7819 (11) ÅCell parameters from 2754 reflections
b = 5.8314 (16) Åθ = 10.6–136.1°
c = 16.754 (4) ŵ = 4.16 mm1
α = 94.956 (16)°T = 93 K
β = 95.136 (17)°Platelet, red
γ = 90.660 (18)°0.60 × 0.40 × 0.05 mm
V = 366.56 (17) Å3
Data collection top
Rigaku R-AXIS RAPID Imaging Plate
diffractometer
1057 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.042
48 frames, Δω = 15° scansθmax = 68.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 44
Tmin = 0.179, Tmax = 0.812k = 77
3027 measured reflectionsl = 2020
1217 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056 w = 1/[σ2(Fo2) + (0.116P)2 + 0.1655P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.178(Δ/σ)max < 0.001
S = 1.14Δρmax = 0.50 e Å3
1217 reflectionsΔρmin = 0.40 e Å3
119 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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
Cl10.4088 (3)0.29421 (15)0.05640 (5)0.0320 (4)
O10.8114 (6)0.4225 (4)0.36973 (13)0.0214 (6)
N10.2423 (8)0.1846 (5)0.34689 (15)0.0188 (7)
H1N0.12570.31730.34160.023*
C10.5028 (9)0.2508 (6)0.21544 (18)0.0191 (8)
H10.62160.39630.21900.023*
C20.3647 (10)0.1526 (6)0.14254 (19)0.0209 (8)
C30.1937 (9)0.0652 (6)0.13536 (19)0.0212 (8)
H30.10530.13460.08390.025*
C40.1560 (9)0.1755 (6)0.20261 (19)0.0204 (8)
H40.03840.32150.19780.024*
C50.2892 (9)0.0758 (6)0.27932 (19)0.0187 (8)
C60.4711 (9)0.1387 (6)0.28535 (18)0.0189 (8)
C70.6270 (9)0.2428 (5)0.36308 (18)0.0193 (8)
C80.5593 (9)0.1196 (6)0.43300 (19)0.0184 (8)
C90.3705 (9)0.0945 (6)0.42281 (19)0.0184 (7)
C100.3152 (9)0.2109 (6)0.48948 (19)0.0189 (8)
H100.19050.35460.48250.023*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0455 (7)0.0327 (6)0.0182 (5)0.0079 (4)0.0022 (4)0.0065 (4)
O10.0288 (15)0.0186 (12)0.0168 (11)0.0083 (10)0.0016 (9)0.0029 (9)
N10.0240 (17)0.0173 (14)0.0148 (13)0.0074 (12)0.0000 (11)0.0021 (10)
C10.020 (2)0.0197 (17)0.0178 (16)0.0016 (14)0.0034 (13)0.0039 (13)
C20.024 (2)0.0226 (17)0.0165 (16)0.0014 (14)0.0028 (12)0.0041 (13)
C30.021 (2)0.0255 (17)0.0164 (15)0.0011 (14)0.0010 (13)0.0006 (13)
C40.023 (2)0.0184 (16)0.0186 (16)0.0048 (14)0.0013 (13)0.0017 (13)
C50.020 (2)0.0201 (16)0.0166 (16)0.0004 (14)0.0031 (13)0.0037 (12)
C60.0193 (19)0.0192 (17)0.0178 (17)0.0019 (13)0.0018 (12)0.0004 (13)
C70.023 (2)0.0194 (17)0.0158 (16)0.0004 (14)0.0024 (13)0.0023 (13)
C80.020 (2)0.0172 (16)0.0180 (16)0.0032 (14)0.0025 (13)0.0017 (13)
C90.0208 (19)0.0180 (16)0.0163 (15)0.0007 (13)0.0018 (12)0.0005 (12)
C100.0225 (19)0.0169 (16)0.0171 (16)0.0045 (13)0.0012 (13)0.0019 (13)
Geometric parameters (Å, º) top
Cl1—C21.743 (3)C3—H30.9500
O1—C71.243 (4)C4—C51.411 (4)
N1—C51.369 (4)C4—H40.9500
N1—C91.377 (4)C5—C61.412 (5)
N1—H1N0.8800C6—C71.459 (4)
C1—C21.360 (5)C7—C81.466 (4)
C1—C61.404 (4)C8—C10i1.400 (5)
C1—H10.9500C8—C91.421 (5)
C2—C31.410 (5)C9—C101.386 (5)
C3—C41.362 (4)C10—H100.9500
C5—N1—C9122.6 (3)C4—C5—C6118.9 (3)
C5—N1—H1N118.7C1—C6—C5119.2 (3)
C9—N1—H1N118.7C1—C6—C7120.1 (3)
C2—C1—C6120.4 (3)C5—C6—C7120.7 (3)
C2—C1—H1119.8O1—C7—C6122.3 (3)
C6—C1—H1119.8O1—C7—C8121.8 (3)
C1—C2—C3120.9 (3)C6—C7—C8115.8 (3)
C1—C2—Cl1119.7 (3)C10i—C8—C9119.4 (3)
C3—C2—Cl1119.4 (3)C10i—C8—C7120.1 (3)
C4—C3—C2119.6 (3)C9—C8—C7120.5 (3)
C4—C3—H3120.2N1—C9—C10120.4 (3)
C2—C3—H3120.2N1—C9—C8119.9 (3)
C3—C4—C5120.9 (3)C10—C9—C8119.7 (3)
C3—C4—H4119.5C9—C10—C8i120.9 (3)
C5—C4—H4119.5C9—C10—H10119.5
N1—C5—C4120.7 (3)C8i—C10—H10119.5
N1—C5—C6120.4 (3)
Symmetry code: (i) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O1ii0.882.032.869 (3)159
Symmetry code: (ii) x1, y1, z.
 

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