2,9-Di­chloro-5,12-di­hydro­quino­[2,3-b]­acridine-7,14-dione (red phase)

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.

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

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Computing details

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

Crystal data

C20H10Cl2N2O2	Z = 1
Mr = 381.22	F(000) = 194.00
Triclinic, P1	Dx = 1.727 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.5418 Å
a = 3.7819 (11) Å	Cell parameters from 2754 reflections
b = 5.8314 (16) Å	θ = 10.6–136.1°
c = 16.754 (4) Å	µ = 4.16 mm^−1
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) Å^3

Data collection

Rigaku R-AXIS RAPID Imaging Plate diffractometer	1057 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.042
48 frames, Δω = 15° scans	θmax = 68.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −4→4
Tmin = 0.179, Tmax = 0.812	k = −7→7
3027 measured reflections	l = −20→20
1217 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.056	w = 1/[σ^2(Fo^2) + (0.116P)^2 + 0.1655P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.178	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.50 e Å^−3
1217 reflections	Δρmin = −0.40 e Å^−3
119 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.4088 (3)	0.29421 (15)	0.05640 (5)	0.0320 (4)
O1	0.8114 (6)	0.4225 (4)	0.36973 (13)	0.0214 (6)
N1	0.2423 (8)	−0.1846 (5)	0.34689 (15)	0.0188 (7)
H1N	0.1257	−0.3173	0.3416	0.023*
C1	0.5028 (9)	0.2508 (6)	0.21544 (18)	0.0191 (8)
H1	0.6216	0.3963	0.2190	0.023*
C2	0.3647 (10)	0.1526 (6)	0.14254 (19)	0.0209 (8)
C3	0.1937 (9)	−0.0652 (6)	0.13536 (19)	0.0212 (8)
H3	0.1053	−0.1346	0.0839	0.025*
C4	0.1560 (9)	−0.1755 (6)	0.20261 (19)	0.0204 (8)
H4	0.0384	−0.3215	0.1978	0.024*
C5	0.2892 (9)	−0.0758 (6)	0.27932 (19)	0.0187 (8)
C6	0.4711 (9)	0.1387 (6)	0.28535 (18)	0.0189 (8)
C7	0.6270 (9)	0.2428 (5)	0.36308 (18)	0.0193 (8)
C8	0.5593 (9)	0.1196 (6)	0.43300 (19)	0.0184 (8)
C9	0.3705 (9)	−0.0945 (6)	0.42281 (19)	0.0184 (7)
C10	0.3152 (9)	−0.2109 (6)	0.48948 (19)	0.0189 (8)
H10	0.1905	−0.3546	0.4825	0.023*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0455 (7)	0.0327 (6)	0.0182 (5)	−0.0079 (4)	0.0022 (4)	0.0065 (4)
O1	0.0288 (15)	0.0186 (12)	0.0168 (11)	−0.0083 (10)	0.0016 (9)	0.0029 (9)
N1	0.0240 (17)	0.0173 (14)	0.0148 (13)	−0.0074 (12)	0.0000 (11)	0.0021 (10)
C1	0.020 (2)	0.0197 (17)	0.0178 (16)	−0.0016 (14)	0.0034 (13)	0.0039 (13)
C2	0.024 (2)	0.0226 (17)	0.0165 (16)	−0.0014 (14)	0.0028 (12)	0.0041 (13)
C3	0.021 (2)	0.0255 (17)	0.0164 (15)	−0.0011 (14)	0.0010 (13)	0.0006 (13)
C4	0.023 (2)	0.0184 (16)	0.0186 (16)	−0.0048 (14)	0.0013 (13)	−0.0017 (13)
C5	0.020 (2)	0.0201 (16)	0.0166 (16)	0.0004 (14)	0.0031 (13)	0.0037 (12)
C6	0.0193 (19)	0.0192 (17)	0.0178 (17)	−0.0019 (13)	0.0018 (12)	0.0004 (13)
C7	0.023 (2)	0.0194 (17)	0.0158 (16)	0.0004 (14)	0.0024 (13)	0.0023 (13)
C8	0.020 (2)	0.0172 (16)	0.0180 (16)	−0.0032 (14)	0.0025 (13)	0.0017 (13)
C9	0.0208 (19)	0.0180 (16)	0.0163 (15)	−0.0007 (13)	0.0018 (12)	0.0005 (12)
C10	0.0225 (19)	0.0169 (16)	0.0171 (16)	−0.0045 (13)	0.0012 (13)	0.0019 (13)

Geometric parameters (Å, º)

Cl1—C2	1.743 (3)	C3—H3	0.9500
O1—C7	1.243 (4)	C4—C5	1.411 (4)
N1—C5	1.369 (4)	C4—H4	0.9500
N1—C9	1.377 (4)	C5—C6	1.412 (5)
N1—H1N	0.8800	C6—C7	1.459 (4)
C1—C2	1.360 (5)	C7—C8	1.466 (4)
C1—C6	1.404 (4)	C8—C10^i	1.400 (5)
C1—H1	0.9500	C8—C9	1.421 (5)
C2—C3	1.410 (5)	C9—C10	1.386 (5)
C3—C4	1.362 (4)	C10—H10	0.9500
C5—N1—C9	122.6 (3)	C4—C5—C6	118.9 (3)
C5—N1—H1N	118.7	C1—C6—C5	119.2 (3)
C9—N1—H1N	118.7	C1—C6—C7	120.1 (3)
C2—C1—C6	120.4 (3)	C5—C6—C7	120.7 (3)
C2—C1—H1	119.8	O1—C7—C6	122.3 (3)
C6—C1—H1	119.8	O1—C7—C8	121.8 (3)
C1—C2—C3	120.9 (3)	C6—C7—C8	115.8 (3)
C1—C2—Cl1	119.7 (3)	C10^i—C8—C9	119.4 (3)
C3—C2—Cl1	119.4 (3)	C10^i—C8—C7	120.1 (3)
C4—C3—C2	119.6 (3)	C9—C8—C7	120.5 (3)
C4—C3—H3	120.2	N1—C9—C10	120.4 (3)
C2—C3—H3	120.2	N1—C9—C8	119.9 (3)
C3—C4—C5	120.9 (3)	C10—C9—C8	119.7 (3)
C3—C4—H4	119.5	C9—C10—C8^i	120.9 (3)
C5—C4—H4	119.5	C9—C10—H10	119.5
N1—C5—C4	120.7 (3)	C8^i—C10—H10	119.5
N1—C5—C6	120.4 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1^ii	0.88	2.03	2.869 (3)	159

Symmetry code: (ii) x−1, y−1, z.