Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032179/hg6107sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032179/hg6107Isup2.hkl |
CCDC reference: 262456
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.036
- wR factor = 0.079
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.752 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 49 Perc. PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT230_ALERT_2_C Hirshfeld Test Diff for Cl2 - C20 .. 5.14 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 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: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: WinGX (Farrugia, 1997) and PARST (Nardelli, 1995).
C21H16Cl2N4 | F(000) = 1632 |
Mr = 395.28 | Dx = 1.392 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 14312 reflections |
a = 23.5075 (13) Å | θ = 1.7–25.7° |
b = 13.9199 (10) Å | µ = 0.36 mm−1 |
c = 11.531 (8) Å | T = 293 K |
V = 3773 (3) Å3 | Plate, colorless |
Z = 8 | 0.42 × 0.25 × 0.10 mm |
Stoe IPDS-II diffractometer | 3705 independent reflections |
Radiation source: fine-focus sealed tube | 1822 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.096 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.7° |
ω scans | h = −28→28 |
Absorption correction: integration (X-RED32; Stoe & Cie 2002) | k = −17→17 |
Tmin = 0.882, Tmax = 0.968 | l = −13→14 |
36036 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.079 | w = 1/[σ2(Fo2) + (0.0403P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.75 | (Δ/σ)max = 0.001 |
3705 reflections | Δρmax = 0.14 e Å−3 |
249 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00149 (16) |
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. |
x | y | z | Uiso*/Ueq | ||
C16 | 0.43219 (11) | 0.2405 (2) | 0.0230 (3) | 0.0795 (8) | |
H16 | 0.4547 | 0.2740 | 0.0755 | 0.095* | |
Cl1 | 0.38978 (3) | 0.09506 (5) | 0.30725 (6) | 0.0712 (2) | |
C17 | 0.37396 (10) | 0.23614 (17) | 0.0386 (2) | 0.0640 (7) | |
H17 | 0.3574 | 0.2662 | 0.1023 | 0.077* | |
C15 | 0.45694 (13) | 0.1949 (2) | −0.0709 (3) | 0.0931 (10) | |
H15 | 0.4961 | 0.1981 | −0.0820 | 0.112* | |
N3 | 0.26983 (8) | 0.17447 (13) | 0.18068 (16) | 0.0492 (5) | |
C8 | 0.08401 (10) | 0.20954 (18) | 0.2701 (2) | 0.0656 (7) | |
H8 | 0.0792 | 0.2483 | 0.3350 | 0.079* | |
C7 | 0.13296 (9) | 0.21687 (16) | 0.2046 (2) | 0.0557 (6) | |
H7 | 0.1609 | 0.2608 | 0.2254 | 0.067* | |
C12 | 0.34009 (10) | 0.18709 (16) | −0.0401 (2) | 0.0557 (6) | |
C24 | 0.36721 (9) | 0.02287 (15) | 0.1941 (2) | 0.0532 (6) | |
C18 | 0.26660 (9) | 0.07805 (15) | 0.23125 (18) | 0.0514 (6) | |
H18A | 0.2286 | 0.0522 | 0.2217 | 0.062* | |
H18B | 0.2751 | 0.0808 | 0.3135 | 0.062* | |
N4 | 0.24637 (8) | 0.17897 (12) | 0.06831 (15) | 0.0479 (4) | |
C14 | 0.42387 (15) | 0.1452 (2) | −0.1471 (3) | 0.0922 (9) | |
H14 | 0.4407 | 0.1135 | −0.2092 | 0.111* | |
C23 | 0.40785 (11) | −0.02410 (18) | 0.1293 (2) | 0.0678 (7) | |
H23 | 0.4462 | −0.0177 | 0.1473 | 0.081* | |
C3 | 0.27783 (10) | 0.18206 (15) | −0.0315 (2) | 0.0529 (6) | |
C9 | 0.04250 (11) | 0.1451 (2) | 0.2395 (2) | 0.0752 (8) | |
H9 | 0.0096 | 0.1401 | 0.2839 | 0.090* | |
C19 | 0.30904 (9) | 0.01473 (14) | 0.17057 (18) | 0.0484 (5) | |
C13 | 0.36570 (12) | 0.14162 (18) | −0.1332 (2) | 0.0736 (7) | |
H13 | 0.3435 | 0.1084 | −0.1866 | 0.088* | |
C6 | 0.14062 (9) | 0.15939 (16) | 0.10849 (19) | 0.0522 (6) | |
C5 | 0.19076 (9) | 0.16790 (15) | 0.0334 (2) | 0.0513 (6) | |
N2 | 0.24381 (9) | 0.17586 (13) | −0.12159 (16) | 0.0611 (5) | |
N1 | 0.18845 (8) | 0.16650 (14) | −0.08001 (17) | 0.0606 (5) | |
C22 | 0.39108 (12) | −0.08031 (18) | 0.0380 (2) | 0.0754 (7) | |
H22 | 0.4184 | −0.1103 | −0.0078 | 0.091* | |
C10 | 0.04949 (11) | 0.0882 (2) | 0.1437 (3) | 0.0796 (8) | |
H10 | 0.0211 | 0.0448 | 0.1232 | 0.096* | |
C11 | 0.09824 (10) | 0.09459 (18) | 0.0773 (2) | 0.0680 (7) | |
H11 | 0.1027 | 0.0559 | 0.0122 | 0.082* | |
C20 | 0.29440 (10) | −0.04689 (15) | 0.0812 (2) | 0.0532 (6) | |
C21 | 0.33454 (12) | −0.09303 (17) | 0.0131 (2) | 0.0672 (7) | |
H21 | 0.3233 | −0.1319 | −0.0484 | 0.081* | |
Cl2 | 0.22309 (3) | −0.06788 (4) | 0.05001 (5) | 0.0719 (2) | |
H3 | 0.2553 (9) | 0.2212 (15) | 0.2237 (19) | 0.056 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C16 | 0.0559 (17) | 0.0874 (19) | 0.095 (2) | −0.0009 (15) | −0.0037 (16) | 0.0261 (18) |
Cl1 | 0.0613 (4) | 0.0792 (4) | 0.0731 (4) | −0.0028 (3) | −0.0119 (3) | −0.0127 (4) |
C17 | 0.0535 (15) | 0.0669 (15) | 0.0716 (18) | 0.0035 (12) | 0.0041 (13) | 0.0125 (14) |
C15 | 0.0628 (19) | 0.101 (2) | 0.115 (3) | 0.0200 (18) | 0.026 (2) | 0.042 (2) |
N3 | 0.0534 (11) | 0.0518 (12) | 0.0424 (11) | 0.0034 (9) | −0.0009 (9) | −0.0036 (10) |
C8 | 0.0562 (16) | 0.0870 (19) | 0.0535 (16) | 0.0089 (14) | 0.0000 (13) | 0.0011 (14) |
C7 | 0.0510 (14) | 0.0654 (15) | 0.0506 (15) | 0.0015 (11) | −0.0047 (12) | 0.0024 (13) |
C12 | 0.0595 (15) | 0.0518 (13) | 0.0559 (15) | 0.0067 (11) | 0.0106 (13) | 0.0110 (12) |
C24 | 0.0556 (14) | 0.0510 (13) | 0.0529 (14) | 0.0009 (11) | −0.0019 (12) | 0.0013 (11) |
C18 | 0.0496 (13) | 0.0641 (15) | 0.0404 (12) | −0.0013 (11) | −0.0010 (10) | 0.0029 (12) |
N4 | 0.0503 (11) | 0.0505 (10) | 0.0430 (10) | −0.0005 (8) | −0.0008 (9) | −0.0004 (9) |
C14 | 0.092 (2) | 0.096 (2) | 0.089 (2) | 0.0221 (19) | 0.032 (2) | 0.0161 (19) |
C23 | 0.0610 (16) | 0.0668 (16) | 0.0757 (18) | 0.0104 (13) | 0.0031 (14) | 0.0004 (15) |
C3 | 0.0595 (15) | 0.0491 (13) | 0.0500 (14) | 0.0013 (11) | 0.0077 (13) | 0.0030 (11) |
C9 | 0.0504 (16) | 0.098 (2) | 0.077 (2) | −0.0021 (15) | 0.0047 (14) | 0.0080 (17) |
C19 | 0.0566 (14) | 0.0465 (12) | 0.0420 (13) | −0.0011 (11) | 0.0002 (11) | 0.0065 (11) |
C13 | 0.0773 (19) | 0.0735 (17) | 0.0701 (18) | 0.0056 (14) | 0.0205 (15) | 0.0054 (15) |
C6 | 0.0463 (14) | 0.0585 (14) | 0.0518 (14) | 0.0017 (11) | −0.0038 (11) | 0.0055 (12) |
C5 | 0.0542 (15) | 0.0516 (13) | 0.0480 (14) | 0.0007 (11) | −0.0058 (12) | −0.0005 (11) |
N2 | 0.0662 (13) | 0.0690 (13) | 0.0481 (11) | −0.0001 (10) | 0.0000 (11) | 0.0060 (11) |
N1 | 0.0613 (13) | 0.0699 (13) | 0.0506 (13) | −0.0018 (10) | −0.0025 (10) | 0.0020 (10) |
C22 | 0.085 (2) | 0.0667 (17) | 0.0749 (19) | 0.0208 (15) | 0.0094 (16) | −0.0075 (15) |
C10 | 0.0572 (17) | 0.089 (2) | 0.093 (2) | −0.0132 (14) | −0.0015 (15) | −0.0045 (18) |
C11 | 0.0561 (16) | 0.0769 (17) | 0.0710 (17) | −0.0056 (13) | −0.0023 (13) | −0.0102 (14) |
C20 | 0.0614 (15) | 0.0466 (12) | 0.0515 (14) | −0.0017 (11) | −0.0053 (12) | 0.0040 (11) |
C21 | 0.092 (2) | 0.0525 (14) | 0.0575 (16) | 0.0075 (14) | −0.0043 (15) | −0.0071 (12) |
Cl2 | 0.0760 (4) | 0.0719 (4) | 0.0678 (4) | −0.0145 (3) | −0.0128 (3) | −0.0052 (3) |
C16—C17 | 1.382 (3) | N4—C3 | 1.369 (3) |
C16—C15 | 1.383 (4) | N4—C5 | 1.376 (3) |
C16—H16 | 0.9300 | C14—C13 | 1.378 (4) |
Cl1—C24 | 1.730 (2) | C14—H14 | 0.9300 |
C17—C12 | 1.387 (3) | C23—C22 | 1.370 (3) |
C17—H17 | 0.9300 | C23—H23 | 0.9300 |
C15—C14 | 1.362 (4) | C3—N2 | 1.313 (3) |
C15—H15 | 0.9300 | C9—C10 | 1.369 (4) |
N3—N4 | 1.410 (2) | C9—H9 | 0.9300 |
N3—C18 | 1.465 (3) | C19—C20 | 1.385 (3) |
N3—H3 | 0.89 (2) | C13—H13 | 0.9300 |
C8—C9 | 1.371 (3) | C6—C11 | 1.391 (3) |
C8—C7 | 1.380 (3) | C6—C5 | 1.467 (3) |
C8—H8 | 0.9300 | C5—N1 | 1.309 (3) |
C7—C6 | 1.379 (3) | N2—N1 | 1.393 (3) |
C7—H7 | 0.9300 | C22—C21 | 1.371 (3) |
C12—C13 | 1.384 (3) | C22—H22 | 0.9300 |
C12—C3 | 1.469 (3) | C10—C11 | 1.381 (3) |
C24—C23 | 1.378 (3) | C10—H10 | 0.9300 |
C24—C19 | 1.399 (3) | C11—H11 | 0.9300 |
C18—C19 | 1.504 (3) | C20—C21 | 1.385 (3) |
C18—H18A | 0.9700 | C20—Cl2 | 1.739 (2) |
C18—H18B | 0.9700 | C21—H21 | 0.9300 |
C17—C16—C15 | 119.9 (3) | C22—C23—H23 | 120.4 |
C17—C16—H16 | 120.0 | C24—C23—H23 | 120.4 |
C15—C16—H16 | 120.0 | N2—C3—N4 | 109.5 (2) |
C16—C17—C12 | 120.3 (3) | N2—C3—C12 | 123.9 (2) |
C16—C17—H17 | 119.9 | N4—C3—C12 | 126.6 (2) |
C12—C17—H17 | 119.9 | C10—C9—C8 | 120.0 (2) |
C14—C15—C16 | 119.9 (3) | C10—C9—H9 | 120.0 |
C14—C15—H15 | 120.1 | C8—C9—H9 | 120.0 |
C16—C15—H15 | 120.1 | C20—C19—C24 | 115.9 (2) |
N4—N3—C18 | 112.72 (16) | C20—C19—C18 | 123.0 (2) |
N4—N3—H3 | 109.3 (14) | C24—C19—C18 | 120.73 (19) |
C18—N3—H3 | 115.4 (13) | C14—C13—C12 | 120.4 (3) |
C9—C8—C7 | 120.1 (2) | C14—C13—H13 | 119.8 |
C9—C8—H8 | 120.0 | C12—C13—H13 | 119.8 |
C7—C8—H8 | 120.0 | C7—C6—C11 | 119.4 (2) |
C6—C7—C8 | 120.4 (2) | C7—C6—C5 | 122.2 (2) |
C6—C7—H7 | 119.8 | C11—C6—C5 | 118.4 (2) |
C8—C7—H7 | 119.8 | N1—C5—N4 | 109.5 (2) |
C13—C12—C17 | 118.9 (2) | N1—C5—C6 | 123.7 (2) |
C13—C12—C3 | 117.6 (2) | N4—C5—C6 | 126.8 (2) |
C17—C12—C3 | 123.5 (2) | C3—N2—N1 | 107.63 (18) |
C23—C24—C19 | 122.3 (2) | C5—N1—N2 | 107.69 (18) |
C23—C24—Cl1 | 118.16 (19) | C23—C22—C21 | 120.9 (2) |
C19—C24—Cl1 | 119.53 (17) | C23—C22—H22 | 119.5 |
N3—C18—C19 | 108.50 (17) | C21—C22—H22 | 119.5 |
N3—C18—H18A | 110.0 | C9—C10—C11 | 120.6 (2) |
C19—C18—H18A | 110.0 | C9—C10—H10 | 119.7 |
N3—C18—H18B | 110.0 | C11—C10—H10 | 119.7 |
C19—C18—H18B | 110.0 | C10—C11—C6 | 119.5 (2) |
H18A—C18—H18B | 108.4 | C10—C11—H11 | 120.2 |
C3—N4—C5 | 105.70 (19) | C6—C11—H11 | 120.2 |
C3—N4—N3 | 124.27 (18) | C19—C20—C21 | 122.7 (2) |
C5—N4—N3 | 129.44 (18) | C19—C20—Cl2 | 119.84 (18) |
C15—C14—C13 | 120.6 (3) | C21—C20—Cl2 | 117.50 (19) |
C15—C14—H14 | 119.7 | C22—C21—C20 | 118.8 (2) |
C13—C14—H14 | 119.7 | C22—C21—H21 | 120.6 |
C22—C23—C24 | 119.2 (2) | C20—C21—H21 | 120.6 |
C15—C16—C17—C12 | −0.7 (4) | C3—C12—C13—C14 | 178.8 (2) |
C17—C16—C15—C14 | −0.5 (4) | C8—C7—C6—C11 | 0.7 (3) |
C9—C8—C7—C6 | −0.3 (3) | C8—C7—C6—C5 | 177.1 (2) |
C16—C17—C12—C13 | 0.9 (3) | C3—N4—C5—N1 | −1.3 (2) |
C16—C17—C12—C3 | −177.8 (2) | N3—N4—C5—N1 | −172.70 (19) |
N4—N3—C18—C19 | 72.4 (2) | C3—N4—C5—C6 | 179.1 (2) |
C18—N3—N4—C3 | −103.2 (2) | N3—N4—C5—C6 | 7.7 (3) |
C18—N3—N4—C5 | 66.8 (3) | C7—C6—C5—N1 | −136.5 (2) |
C16—C15—C14—C13 | 1.4 (5) | C11—C6—C5—N1 | 39.9 (3) |
C19—C24—C23—C22 | 0.5 (4) | C7—C6—C5—N4 | 43.1 (3) |
Cl1—C24—C23—C22 | −178.87 (19) | C11—C6—C5—N4 | −140.5 (2) |
C5—N4—C3—N2 | 1.5 (2) | N4—C3—N2—N1 | −1.2 (2) |
N3—N4—C3—N2 | 173.51 (18) | C12—C3—N2—N1 | 176.32 (19) |
C5—N4—C3—C12 | −175.9 (2) | N4—C5—N1—N2 | 0.6 (2) |
N3—N4—C3—C12 | −3.9 (3) | C6—C5—N1—N2 | −179.77 (19) |
C13—C12—C3—N2 | −30.1 (3) | C3—N2—N1—C5 | 0.4 (2) |
C17—C12—C3—N2 | 148.7 (2) | C24—C23—C22—C21 | −2.4 (4) |
C13—C12—C3—N4 | 147.0 (2) | C8—C9—C10—C11 | 0.3 (4) |
C17—C12—C3—N4 | −34.2 (3) | C9—C10—C11—C6 | 0.2 (4) |
C7—C8—C9—C10 | −0.2 (4) | C7—C6—C11—C10 | −0.7 (4) |
C23—C24—C19—C20 | 2.7 (3) | C5—C6—C11—C10 | −177.2 (2) |
Cl1—C24—C19—C20 | −177.91 (15) | C24—C19—C20—C21 | −4.3 (3) |
C23—C24—C19—C18 | −170.8 (2) | C18—C19—C20—C21 | 169.1 (2) |
Cl1—C24—C19—C18 | 8.5 (3) | C24—C19—C20—Cl2 | 176.27 (16) |
N3—C18—C19—C20 | −98.0 (2) | C18—C19—C20—Cl2 | −10.3 (3) |
N3—C18—C19—C24 | 75.1 (2) | C23—C22—C21—C20 | 0.8 (4) |
C15—C14—C13—C12 | −1.2 (4) | C19—C20—C21—C22 | 2.7 (4) |
C17—C12—C13—C14 | 0.0 (4) | Cl2—C20—C21—C22 | −177.92 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N2i | 0.89 (2) | 2.30 (2) | 3.148 (3) | 159.1 (19) |
C7—H7···N1i | 0.93 | 2.54 | 3.241 (3) | 132 |
C17—H17···N3 | 0.93 | 2.59 | 3.068 (3) | 113 |
C18—H18A···Cl2 | 0.97 | 2.59 | 3.089 (2) | 112 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
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