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The title compound, C22H16N6·2CHCl3, a diketopyrrolo­pyrrole analogue (red pigment), has Ci symmetry and the phenyl rings are at an angle of 53.5 (1)° to the planar heterocylic ring system.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019172/ob6291sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019172/ob6291Isup2.hkl
Contains datablock I

CCDC reference: 225705

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.043
  • wR factor = 0.118
  • Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: TEXSAN (Molecular Structure Corporation, 2001); program(s) used to solve structure: SHELXS86 (Sheldrick 1985); program(s) used to refine structure: TEXSAN; molecular graphics: ORTEP-III (Burnett & Johnson, 1996); software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C22H16N6·2CHCl3F(000) = 612.0
Mr = 603.16Dx = 1.539 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybcCell parameters from 6142 reflections
a = 8.656 (3) Åθ = 4.0–67.6°
b = 13.768 (7) ŵ = 6.25 mm1
c = 11.670 (5) ÅT = 93 K
β = 110.61 (2)°Platelet, red
V = 1301.8 (10) Å30.3 × 0.15 × 0.02 mm
Z = 2
Data collection top
Rigaku RAXIS-RAPID Imaging Plate
diffractometer
1924 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.074
48 frames, delta ω = 15 deg scansθmax = 68.2°
Absorption correction: multi-scan
(Higashi, 1995)
h = 99
Tmin = 0.396, Tmax = 0.883k = 1616
11504 measured reflectionsl = 1414
2361 independent reflections
Refinement top
Refinement on F2H-atom parameters not refined
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.05(Max(Fo2,0) + 2Fc2)/3)2]
wR(F2) = 0.118(Δ/σ)max = 0.010
S = 1.29Δρmax = 0.48 e Å3
2235 reflectionsΔρmin = 0.42 e Å3
163 parameters
Special details top

Refinement. Refinement using reflections with F2 > -3.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). The reflections whose |Fo2Φc2\/σ(Fo2) are greater than 5% have not been used for the refinement.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.62330 (8)0.84981 (4)0.32331 (6)0.0335 (2)
Cl20.91335 (9)0.72697 (5)0.41190 (7)0.0395 (2)
Cl30.74563 (9)0.78599 (5)0.57591 (6)0.0340 (2)
N10.0940 (3)0.5311 (1)0.1411 (2)0.0227 (5)
N20.3306 (2)0.5837 (1)0.0148 (2)0.0240 (5)
N30.5220 (3)0.5981 (2)0.2302 (2)0.0300 (6)
C10.1567 (3)0.4443 (2)0.2762 (2)0.0237 (6)
C20.2096 (3)0.5004 (2)0.3846 (2)0.0266 (7)
C30.3044 (3)0.4577 (2)0.4942 (2)0.0334 (7)
C40.3464 (3)0.3599 (2)0.4984 (2)0.0313 (7)
C50.2967 (3)0.3047 (2)0.3924 (2)0.0288 (7)
C60.2025 (3)0.3467 (2)0.2816 (2)0.0246 (6)
C70.0538 (3)0.4848 (2)0.1580 (2)0.0225 (6)
C80.1675 (3)0.5453 (2)0.2357 (2)0.0290 (7)
C90.1802 (3)0.5503 (2)0.0170 (2)0.0220 (6)
C100.0713 (3)0.4795 (2)0.0450 (2)0.0227 (6)
C110.4256 (3)0.5906 (2)0.1321 (2)0.0229 (6)
C120.7205 (3)0.7540 (2)0.4239 (2)0.0274 (7)
H10.18030.56720.38210.0319*
H20.34080.49540.56710.0401*
H30.40950.33070.57440.0376*
H40.32710.23810.39560.0346*
H50.16910.30880.20890.0296*
H60.26920.57930.20160.0348*
H70.09430.58200.30130.0348*
H80.18650.48390.26530.0348*
H90.65210.69780.40180.0329*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0392 (4)0.0267 (4)0.0300 (3)0.0023 (3)0.0064 (3)0.0015 (2)
Cl20.0363 (4)0.0418 (4)0.0416 (4)0.0037 (3)0.0153 (3)0.0083 (3)
Cl30.0447 (5)0.0328 (4)0.0252 (3)0.0042 (3)0.0131 (3)0.0044 (2)
N10.030 (1)0.0183 (10)0.0196 (10)0.0007 (8)0.0080 (9)0.0016 (8)
N20.028 (1)0.0198 (10)0.023 (1)0.0025 (9)0.0070 (9)0.0010 (8)
N30.034 (1)0.027 (1)0.027 (1)0.0012 (10)0.009 (1)0.0034 (9)
C10.027 (1)0.024 (1)0.020 (1)0.002 (1)0.008 (1)0.0008 (10)
C20.033 (2)0.022 (1)0.023 (1)0.002 (1)0.007 (1)0.001 (1)
C30.032 (2)0.044 (2)0.023 (1)0.005 (1)0.007 (1)0.005 (1)
C40.030 (2)0.040 (2)0.024 (1)0.001 (1)0.009 (1)0.009 (1)
C50.030 (1)0.023 (1)0.033 (1)0.000 (1)0.010 (1)0.007 (1)
C60.030 (1)0.019 (1)0.025 (1)0.003 (1)0.010 (1)0.0009 (10)
C70.029 (1)0.014 (1)0.023 (1)0.0022 (10)0.006 (1)0.0016 (9)
C80.036 (2)0.028 (1)0.023 (1)0.003 (1)0.012 (1)0.0014 (10)
C90.028 (1)0.017 (1)0.021 (1)0.0015 (10)0.008 (1)0.0020 (9)
C100.027 (1)0.017 (1)0.020 (1)0.0023 (10)0.004 (1)0.0010 (9)
C110.025 (1)0.018 (1)0.028 (1)0.0012 (10)0.012 (1)0.0003 (10)
C120.031 (2)0.024 (1)0.026 (1)0.001 (1)0.008 (1)0.002 (1)
Geometric parameters (Å, º) top
Cl1—C121.771 (3)C3—C41.390 (4)
Cl2—C121.765 (3)C3—H20.950
Cl3—C121.765 (3)C4—C51.386 (4)
N1—C71.377 (3)C4—H30.950
N1—C81.468 (3)C5—C61.388 (3)
N1—C91.401 (3)C5—H40.951
N2—C91.304 (3)C6—H50.951
N2—C111.330 (3)C7—C101.381 (3)
N3—C111.160 (3)C8—H60.950
C1—C21.414 (3)C8—H70.950
C1—C61.395 (3)C8—H80.950
C1—C71.463 (3)C9—C10i1.434 (3)
C2—C31.383 (3)C10—C10i1.425 (4)
C2—H10.950C12—H90.951
Cl1···C11ii3.407 (2)Cl3···C11v3.503 (3)
Cl1···C10iii3.466 (3)N2···C5vi3.330 (3)
Cl1···C7iii3.552 (3)N3···C123.148 (3)
Cl1···C9ii3.594 (3)N3···C8iv3.317 (4)
Cl2···C5iv3.435 (3)N3···C3vii3.598 (3)
Cl2···C6iv3.508 (3)C3···C3viii3.538 (4)
Cl3···N3v3.463 (3)
C7—N1—C8125.4 (2)N1—C7—C1122.3 (2)
C7—N1—C9111.3 (2)N1—C7—C10107.2 (2)
C8—N1—C9122.6 (2)C1—C7—C10130.2 (2)
C9—N2—C11120.7 (2)N1—C8—H6109.5
C2—C1—C6119.2 (2)N1—C8—H7109.4
C2—C1—C7122.3 (2)N1—C8—H8109.4
C6—C1—C7118.4 (2)H6—C8—H7109.5
C1—C2—C3119.7 (2)H6—C8—H8109.5
C1—C2—H1120.1H7—C8—H8109.5
C3—C2—H1120.1N1—C9—N2118.4 (2)
C2—C3—C4120.3 (2)N1—C9—C10i105.2 (2)
C2—C3—H2119.9N2—C9—C10i136.3 (2)
C4—C3—H2119.8C7—C10—C9i144.0 (2)
C3—C4—C5120.3 (2)C7—C10—C10i109.0 (3)
C3—C4—H3119.8C9i—C10—C10i107.0 (3)
C5—C4—H3119.8N2—C11—N3172.9 (3)
C4—C5—C6120.0 (2)Cl1—C12—Cl2110.4 (1)
C4—C5—H4120.0Cl1—C12—Cl3110.0 (1)
C6—C5—H4120.0Cl1—C12—H9108.7
C1—C6—C5120.4 (2)Cl2—C12—Cl3110.3 (1)
C1—C6—H5119.8Cl2—C12—H9108.7
C5—C6—H5119.8Cl3—C12—H9108.7
N1—C7—C1—C254.3 (3)C4—C3—C2—H1179.5
N1—C7—C1—C6125.2 (3)C4—C5—C6—H5179.7
N1—C7—C10—C9i176.5 (3)C5—C4—C3—H2178.7
N1—C7—C10—C10i1.9 (3)C5—C6—C1—C7178.4 (2)
N1—C9—N2—C11170.7 (2)C6—C1—C2—H1179.3
N1—C9—C10i—C7i178.2 (3)C6—C1—C7—C1049.0 (4)
N1—C9—C10i—C103.4 (3)C6—C5—C4—H3179.1
N2—C9—N1—C7172.3 (2)C7—N1—C8—H6179.8
N2—C9—N1—C81.2 (3)C7—N1—C8—H759.8
N2—C9—C10i—C7i5.6 (6)C7—N1—C8—H860.1
N2—C9—C10i—C10172.8 (3)C7—N1—C9—C10i4.8 (2)
C1—C2—C3—C40.6 (4)C7—C1—C2—H11.2
C1—C2—C3—H2179.5C7—C1—C6—H51.6
C1—C6—C5—C40.3 (4)C7—C10—C10i—C7i180.0
C1—C6—C5—H4179.7C7—C10—C10i—C91.0 (3)
C1—C7—N1—C80.4 (4)C8—N1—C7—C10175.0 (2)
C1—C7—N1—C9171.2 (2)C8—N1—C9—C10i175.8 (2)
C1—C7—C10—C9i8.6 (5)C9—N1—C7—C104.2 (3)
C1—C7—C10—C10i173.0 (2)C9—N1—C8—H610.4
C2—C1—C6—C51.1 (4)C9—N1—C8—H7130.4
C2—C1—C6—H5178.9C9—N1—C8—H8109.6
C2—C1—C7—C10131.5 (3)C9—C10i—C10—C9i180.0
C2—C3—C4—C51.4 (4)C10—C9i—N2i—C11i5.1 (4)
C2—C3—C4—H3178.6H1—C2—C3—H20.5
C3—C2—C1—C60.6 (4)H2—C3—C4—H31.3
C3—C2—C1—C7178.9 (3)H3—C4—C5—H40.9
C3—C4—C5—C60.9 (4)H4—C5—C6—H50.3
C3—C4—C5—H4179.1H4—C5—C6—H50.3
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y+3/2, z+1/2; (iv) x+1, y+1, z; (v) x, y+3/2, z+1/2; (vi) x, y+1/2, z1/2; (vii) x+1, y, z+1; (viii) x1, y+1, z1.
 

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