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
CCDC reference: 225705
Key indicators
- Single-crystal X-ray study
- T = 93 K
- Mean (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
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.
Crystal data top
C22H16N6·2CHCl3 | F(000) = 612.0 |
Mr = 603.16 | Dx = 1.539 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.5418 Å |
Hall symbol: -P 2ybc | Cell parameters from 6142 reflections |
a = 8.656 (3) Å | θ = 4.0–67.6° |
b = 13.768 (7) Å | µ = 6.25 mm−1 |
c = 11.670 (5) Å | T = 93 K |
β = 110.61 (2)° | Platelet, red |
V = 1301.8 (10) Å3 | 0.3 × 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-1 | Rint = 0.074 |
48 frames, delta ω = 15 deg scans | θmax = 68.2° |
Absorption correction: multi-scan (Higashi, 1995) | h = −9→9 |
Tmin = 0.396, Tmax = 0.883 | k = −16→16 |
11504 measured reflections | l = −14→14 |
2361 independent reflections | |
Refinement top
Refinement on F2 | H-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 = 1.29 | Δρmax = 0.48 e Å−3 |
2235 reflections | Δρmin = −0.42 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Cl1 | 0.62330 (8) | 0.84981 (4) | 0.32331 (6) | 0.0335 (2) | |
Cl2 | 0.91335 (9) | 0.72697 (5) | 0.41190 (7) | 0.0395 (2) | |
Cl3 | 0.74563 (9) | 0.78599 (5) | 0.57591 (6) | 0.0340 (2) | |
N1 | 0.0940 (3) | 0.5311 (1) | −0.1411 (2) | 0.0227 (5) | |
N2 | 0.3306 (2) | 0.5837 (1) | 0.0148 (2) | 0.0240 (5) | |
N3 | 0.5220 (3) | 0.5981 (2) | 0.2302 (2) | 0.0300 (6) | |
C1 | −0.1567 (3) | 0.4443 (2) | −0.2762 (2) | 0.0237 (6) | |
C2 | −0.2096 (3) | 0.5004 (2) | −0.3846 (2) | 0.0266 (7) | |
C3 | −0.3044 (3) | 0.4577 (2) | −0.4942 (2) | 0.0334 (7) | |
C4 | −0.3464 (3) | 0.3599 (2) | −0.4984 (2) | 0.0313 (7) | |
C5 | −0.2967 (3) | 0.3047 (2) | −0.3924 (2) | 0.0288 (7) | |
C6 | −0.2025 (3) | 0.3467 (2) | −0.2816 (2) | 0.0246 (6) | |
C7 | −0.0538 (3) | 0.4848 (2) | −0.1580 (2) | 0.0225 (6) | |
C8 | 0.1675 (3) | 0.5453 (2) | −0.2357 (2) | 0.0290 (7) | |
C9 | 0.1802 (3) | 0.5503 (2) | −0.0170 (2) | 0.0220 (6) | |
C10 | −0.0713 (3) | 0.4795 (2) | −0.0450 (2) | 0.0227 (6) | |
C11 | 0.4256 (3) | 0.5906 (2) | 0.1321 (2) | 0.0229 (6) | |
C12 | 0.7205 (3) | 0.7540 (2) | 0.4239 (2) | 0.0274 (7) | |
H1 | −0.1803 | 0.5672 | −0.3821 | 0.0319* | |
H2 | −0.3408 | 0.4954 | −0.5671 | 0.0401* | |
H3 | −0.4095 | 0.3307 | −0.5744 | 0.0376* | |
H4 | −0.3271 | 0.2381 | −0.3956 | 0.0346* | |
H5 | −0.1691 | 0.3088 | −0.2089 | 0.0296* | |
H6 | 0.2692 | 0.5793 | −0.2016 | 0.0348* | |
H7 | 0.0943 | 0.5820 | −0.3013 | 0.0348* | |
H8 | 0.1865 | 0.4839 | −0.2653 | 0.0348* | |
H9 | 0.6521 | 0.6978 | 0.4018 | 0.0329* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0392 (4) | 0.0267 (4) | 0.0300 (3) | −0.0023 (3) | 0.0064 (3) | 0.0015 (2) |
Cl2 | 0.0363 (4) | 0.0418 (4) | 0.0416 (4) | 0.0037 (3) | 0.0153 (3) | −0.0083 (3) |
Cl3 | 0.0447 (5) | 0.0328 (4) | 0.0252 (3) | −0.0042 (3) | 0.0131 (3) | −0.0044 (2) |
N1 | 0.030 (1) | 0.0183 (10) | 0.0196 (10) | 0.0007 (8) | 0.0080 (9) | 0.0016 (8) |
N2 | 0.028 (1) | 0.0198 (10) | 0.023 (1) | −0.0025 (9) | 0.0070 (9) | 0.0010 (8) |
N3 | 0.034 (1) | 0.027 (1) | 0.027 (1) | −0.0012 (10) | 0.009 (1) | −0.0034 (9) |
C1 | 0.027 (1) | 0.024 (1) | 0.020 (1) | 0.002 (1) | 0.008 (1) | −0.0008 (10) |
C2 | 0.033 (2) | 0.022 (1) | 0.023 (1) | 0.002 (1) | 0.007 (1) | 0.001 (1) |
C3 | 0.032 (2) | 0.044 (2) | 0.023 (1) | 0.005 (1) | 0.007 (1) | 0.005 (1) |
C4 | 0.030 (2) | 0.040 (2) | 0.024 (1) | −0.001 (1) | 0.009 (1) | −0.009 (1) |
C5 | 0.030 (1) | 0.023 (1) | 0.033 (1) | 0.000 (1) | 0.010 (1) | −0.007 (1) |
C6 | 0.030 (1) | 0.019 (1) | 0.025 (1) | 0.003 (1) | 0.010 (1) | −0.0009 (10) |
C7 | 0.029 (1) | 0.014 (1) | 0.023 (1) | 0.0022 (10) | 0.006 (1) | 0.0016 (9) |
C8 | 0.036 (2) | 0.028 (1) | 0.023 (1) | −0.003 (1) | 0.012 (1) | −0.0014 (10) |
C9 | 0.028 (1) | 0.017 (1) | 0.021 (1) | 0.0015 (10) | 0.008 (1) | 0.0020 (9) |
C10 | 0.027 (1) | 0.017 (1) | 0.020 (1) | 0.0023 (10) | 0.004 (1) | 0.0010 (9) |
C11 | 0.025 (1) | 0.018 (1) | 0.028 (1) | −0.0012 (10) | 0.012 (1) | 0.0003 (10) |
C12 | 0.031 (2) | 0.024 (1) | 0.026 (1) | −0.001 (1) | 0.008 (1) | −0.002 (1) |
Geometric parameters (Å, º) top
Cl1—C12 | 1.771 (3) | C3—C4 | 1.390 (4) |
Cl2—C12 | 1.765 (3) | C3—H2 | 0.950 |
Cl3—C12 | 1.765 (3) | C4—C5 | 1.386 (4) |
N1—C7 | 1.377 (3) | C4—H3 | 0.950 |
N1—C8 | 1.468 (3) | C5—C6 | 1.388 (3) |
N1—C9 | 1.401 (3) | C5—H4 | 0.951 |
N2—C9 | 1.304 (3) | C6—H5 | 0.951 |
N2—C11 | 1.330 (3) | C7—C10 | 1.381 (3) |
N3—C11 | 1.160 (3) | C8—H6 | 0.950 |
C1—C2 | 1.414 (3) | C8—H7 | 0.950 |
C1—C6 | 1.395 (3) | C8—H8 | 0.950 |
C1—C7 | 1.463 (3) | C9—C10i | 1.434 (3) |
C2—C3 | 1.383 (3) | C10—C10i | 1.425 (4) |
C2—H1 | 0.950 | C12—H9 | 0.951 |
| | | |
Cl1···C11ii | 3.407 (2) | Cl3···C11v | 3.503 (3) |
Cl1···C10iii | 3.466 (3) | N2···C5vi | 3.330 (3) |
Cl1···C7iii | 3.552 (3) | N3···C12 | 3.148 (3) |
Cl1···C9ii | 3.594 (3) | N3···C8iv | 3.317 (4) |
Cl2···C5iv | 3.435 (3) | N3···C3vii | 3.598 (3) |
Cl2···C6iv | 3.508 (3) | C3···C3viii | 3.538 (4) |
Cl3···N3v | 3.463 (3) | | |
| | | |
C7—N1—C8 | 125.4 (2) | N1—C7—C1 | 122.3 (2) |
C7—N1—C9 | 111.3 (2) | N1—C7—C10 | 107.2 (2) |
C8—N1—C9 | 122.6 (2) | C1—C7—C10 | 130.2 (2) |
C9—N2—C11 | 120.7 (2) | N1—C8—H6 | 109.5 |
C2—C1—C6 | 119.2 (2) | N1—C8—H7 | 109.4 |
C2—C1—C7 | 122.3 (2) | N1—C8—H8 | 109.4 |
C6—C1—C7 | 118.4 (2) | H6—C8—H7 | 109.5 |
C1—C2—C3 | 119.7 (2) | H6—C8—H8 | 109.5 |
C1—C2—H1 | 120.1 | H7—C8—H8 | 109.5 |
C3—C2—H1 | 120.1 | N1—C9—N2 | 118.4 (2) |
C2—C3—C4 | 120.3 (2) | N1—C9—C10i | 105.2 (2) |
C2—C3—H2 | 119.9 | N2—C9—C10i | 136.3 (2) |
C4—C3—H2 | 119.8 | C7—C10—C9i | 144.0 (2) |
C3—C4—C5 | 120.3 (2) | C7—C10—C10i | 109.0 (3) |
C3—C4—H3 | 119.8 | C9i—C10—C10i | 107.0 (3) |
C5—C4—H3 | 119.8 | N2—C11—N3 | 172.9 (3) |
C4—C5—C6 | 120.0 (2) | Cl1—C12—Cl2 | 110.4 (1) |
C4—C5—H4 | 120.0 | Cl1—C12—Cl3 | 110.0 (1) |
C6—C5—H4 | 120.0 | Cl1—C12—H9 | 108.7 |
C1—C6—C5 | 120.4 (2) | Cl2—C12—Cl3 | 110.3 (1) |
C1—C6—H5 | 119.8 | Cl2—C12—H9 | 108.7 |
C5—C6—H5 | 119.8 | Cl3—C12—H9 | 108.7 |
| | | |
N1—C7—C1—C2 | −54.3 (3) | C4—C3—C2—H1 | 179.5 |
N1—C7—C1—C6 | 125.2 (3) | C4—C5—C6—H5 | 179.7 |
N1—C7—C10—C9i | 176.5 (3) | C5—C4—C3—H2 | −178.7 |
N1—C7—C10—C10i | −1.9 (3) | C5—C6—C1—C7 | −178.4 (2) |
N1—C9—N2—C11 | −170.7 (2) | C6—C1—C2—H1 | 179.3 |
N1—C9—C10i—C7i | −178.2 (3) | C6—C1—C7—C10 | −49.0 (4) |
N1—C9—C10i—C10 | 3.4 (3) | C6—C5—C4—H3 | 179.1 |
N2—C9—N1—C7 | 172.3 (2) | C7—N1—C8—H6 | 179.8 |
N2—C9—N1—C8 | 1.2 (3) | C7—N1—C8—H7 | 59.8 |
N2—C9—C10i—C7i | 5.6 (6) | C7—N1—C8—H8 | −60.1 |
N2—C9—C10i—C10 | −172.8 (3) | C7—N1—C9—C10i | −4.8 (2) |
C1—C2—C3—C4 | −0.6 (4) | C7—C1—C2—H1 | −1.2 |
C1—C2—C3—H2 | 179.5 | C7—C1—C6—H5 | 1.6 |
C1—C6—C5—C4 | −0.3 (4) | C7—C10—C10i—C7i | −180.0 |
C1—C6—C5—H4 | 179.7 | C7—C10—C10i—C9 | −1.0 (3) |
C1—C7—N1—C8 | −0.4 (4) | C8—N1—C7—C10 | 175.0 (2) |
C1—C7—N1—C9 | −171.2 (2) | C8—N1—C9—C10i | −175.8 (2) |
C1—C7—C10—C9i | −8.6 (5) | C9—N1—C7—C10 | 4.2 (3) |
C1—C7—C10—C10i | 173.0 (2) | C9—N1—C8—H6 | −10.4 |
C2—C1—C6—C5 | 1.1 (4) | C9—N1—C8—H7 | −130.4 |
C2—C1—C6—H5 | −178.9 | C9—N1—C8—H8 | 109.6 |
C2—C1—C7—C10 | 131.5 (3) | C9—C10i—C10—C9i | −180.0 |
C2—C3—C4—C5 | 1.4 (4) | C10—C9i—N2i—C11i | −5.1 (4) |
C2—C3—C4—H3 | −178.6 | H1—C2—C3—H2 | −0.5 |
C3—C2—C1—C6 | −0.6 (4) | H2—C3—C4—H3 | 1.3 |
C3—C2—C1—C7 | 178.9 (3) | H3—C4—C5—H4 | −0.9 |
C3—C4—C5—C6 | −0.9 (4) | H4—C5—C6—H5 | −0.3 |
C3—C4—C5—H4 | 179.1 | H4—C5—C6—H5 | −0.3 |
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, −z−1/2; (vii) x+1, y, z+1; (viii) −x−1, −y+1, −z−1. |