Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805013681/er6014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805013681/er6014Isup2.hkl |
CCDC reference: 274392
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.048
- wR factor = 0.127
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.598 0.939 Tmin' and Tmax expected: 0.860 0.939 RR' = 0.695 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.69
Alert level C PLAT127_ALERT_1_C Implicit Hall Symbol Inconsistent with Explicit P -2yn PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C5 - C6 ... 1.45 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl .. N1 .. 3.28 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 12 N1 -C5 -C6 -N2 -177.00100.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 13 C4 -C5 -C6 -N2 3.00 5.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL.
C14H11ClN2 | F(000) = 504 |
Mr = 242.70 | Dx = 1.318 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yn | Cell parameters from 2106 reflections |
a = 7.5645 (8) Å | θ = 5.7–52.8° |
b = 12.2332 (12) Å | µ = 0.29 mm−1 |
c = 13.5558 (14) Å | T = 293 K |
β = 102.867 (2)° | Prism, colorless |
V = 1222.9 (2) Å3 | 0.51 × 0.39 × 0.22 mm |
Z = 4 |
Brruker SMART 1K CCD area-detector diffractometer | 2668 independent reflections |
Radiation source: fine-focus sealed tube | 1924 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Detector resolution: 10 pixels mm-1 | θmax = 27.0°, θmin = 2.3° |
φ and ω scans to fill Ewald sphere | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −10→15 |
Tmin = 0.598, Tmax = 0.939 | l = −17→17 |
7051 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | All H-atom parameters refined |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0674P)2] where P = (Fo2 + 2Fc2)/3 |
2668 reflections | (Δ/σ)max = 0.001 |
198 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
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 | ||
Cl | 1.04722 (7) | 0.62645 (5) | 0.83201 (4) | 0.0655 (2) | |
N1 | −0.1352 (2) | 0.90726 (14) | 0.53814 (12) | 0.0504 (4) | |
N2 | 0.0153 (3) | 0.71100 (17) | 0.40003 (14) | 0.0718 (6) | |
C1 | −0.1391 (3) | 0.97120 (17) | 0.61681 (18) | 0.0557 (5) | |
C2 | −0.0138 (3) | 0.96808 (17) | 0.70605 (19) | 0.0576 (6) | |
C3 | 0.1268 (3) | 0.89547 (17) | 0.71739 (16) | 0.0499 (5) | |
C4 | 0.1399 (2) | 0.82676 (14) | 0.63801 (13) | 0.0377 (4) | |
C5 | 0.0044 (2) | 0.83719 (14) | 0.55141 (13) | 0.0392 (4) | |
C6 | 0.0074 (3) | 0.76763 (17) | 0.46554 (14) | 0.0485 (5) | |
C7 | 0.2935 (2) | 0.74683 (15) | 0.64606 (15) | 0.0417 (4) | |
C8 | 0.4575 (3) | 0.79654 (18) | 0.6144 (2) | 0.0545 (5) | |
C9 | 0.6095 (2) | 0.71521 (15) | 0.62397 (14) | 0.0450 (5) | |
C10 | 0.6149 (3) | 0.64171 (18) | 0.54665 (18) | 0.0559 (5) | |
C11 | 0.7517 (3) | 0.56415 (19) | 0.55825 (19) | 0.0641 (6) | |
C12 | 0.8838 (3) | 0.55908 (18) | 0.64501 (18) | 0.0570 (6) | |
C13 | 0.8790 (2) | 0.63229 (15) | 0.72087 (16) | 0.0465 (5) | |
C14 | 0.7429 (2) | 0.70954 (15) | 0.71113 (15) | 0.0442 (4) | |
H1 | −0.235 (3) | 1.0181 (17) | 0.6090 (15) | 0.058 (6)* | |
H2 | −0.021 (3) | 1.0144 (19) | 0.7614 (16) | 0.068 (6)* | |
H3 | 0.205 (3) | 0.8886 (15) | 0.7772 (16) | 0.051 (6)* | |
H6 | 0.325 (3) | 0.7213 (17) | 0.7154 (16) | 0.065 (6)* | |
H7 | 0.246 (3) | 0.6795 (17) | 0.6015 (14) | 0.050 (5)* | |
H8 | 0.495 (3) | 0.8646 (19) | 0.6547 (17) | 0.068 (7)* | |
H9 | 0.422 (3) | 0.821 (2) | 0.5466 (18) | 0.077 (7)* | |
H10 | 0.534 (3) | 0.6416 (15) | 0.4868 (15) | 0.049 (6)* | |
H11 | 0.750 (3) | 0.515 (2) | 0.5047 (18) | 0.083 (8)* | |
H12 | 0.977 (3) | 0.5089 (18) | 0.6524 (15) | 0.066 (6)* | |
H14 | 0.745 (3) | 0.7602 (16) | 0.7646 (13) | 0.045 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0432 (3) | 0.0772 (4) | 0.0730 (4) | −0.0040 (2) | 0.0066 (3) | 0.0147 (3) |
N1 | 0.0390 (9) | 0.0495 (10) | 0.0632 (10) | 0.0076 (7) | 0.0128 (8) | 0.0094 (8) |
N2 | 0.0815 (15) | 0.0797 (14) | 0.0536 (11) | 0.0064 (11) | 0.0137 (10) | −0.0098 (10) |
C1 | 0.0447 (12) | 0.0424 (12) | 0.0858 (16) | 0.0097 (9) | 0.0265 (11) | 0.0039 (11) |
C2 | 0.0551 (13) | 0.0460 (12) | 0.0770 (15) | −0.0028 (9) | 0.0259 (11) | −0.0178 (11) |
C3 | 0.0434 (11) | 0.0525 (12) | 0.0531 (12) | −0.0048 (9) | 0.0090 (9) | −0.0101 (9) |
C4 | 0.0315 (8) | 0.0343 (9) | 0.0489 (10) | −0.0026 (7) | 0.0124 (7) | 0.0013 (7) |
C5 | 0.0344 (9) | 0.0378 (10) | 0.0472 (10) | −0.0008 (7) | 0.0128 (8) | 0.0037 (8) |
C6 | 0.0454 (11) | 0.0547 (12) | 0.0438 (10) | 0.0040 (9) | 0.0067 (8) | 0.0039 (9) |
C7 | 0.0337 (9) | 0.0408 (11) | 0.0509 (11) | 0.0033 (8) | 0.0100 (8) | 0.0050 (9) |
C8 | 0.0394 (11) | 0.0449 (12) | 0.0832 (16) | 0.0061 (8) | 0.0222 (10) | 0.0151 (11) |
C9 | 0.0342 (9) | 0.0380 (10) | 0.0676 (12) | −0.0009 (7) | 0.0213 (9) | 0.0080 (9) |
C10 | 0.0435 (12) | 0.0602 (14) | 0.0627 (14) | −0.0023 (9) | 0.0090 (10) | −0.0015 (10) |
C11 | 0.0617 (15) | 0.0548 (14) | 0.0798 (16) | −0.0011 (11) | 0.0243 (13) | −0.0183 (12) |
C12 | 0.0431 (11) | 0.0457 (12) | 0.0857 (16) | 0.0070 (9) | 0.0220 (11) | 0.0007 (11) |
C13 | 0.0334 (9) | 0.0447 (11) | 0.0637 (12) | −0.0045 (8) | 0.0162 (9) | 0.0065 (9) |
C14 | 0.0384 (10) | 0.0398 (11) | 0.0593 (11) | −0.0045 (8) | 0.0215 (9) | 0.0009 (9) |
Cl—C13 | 1.743 (2) | C7—H7 | 1.04 (2) |
N1—C1 | 1.328 (3) | C8—C9 | 1.504 (3) |
N1—C5 | 1.341 (2) | C8—H8 | 1.00 (2) |
N2—C6 | 1.138 (2) | C8—H9 | 0.95 (2) |
C1—C2 | 1.361 (3) | C9—C14 | 1.374 (3) |
C1—H1 | 0.91 (2) | C9—C10 | 1.388 (3) |
C2—C3 | 1.368 (3) | C10—C11 | 1.387 (3) |
C2—H2 | 0.95 (2) | C10—H10 | 0.90 (2) |
C3—C4 | 1.386 (3) | C11—C12 | 1.365 (3) |
C3—H3 | 0.89 (2) | C11—H11 | 0.94 (3) |
C4—C5 | 1.382 (2) | C12—C13 | 1.370 (3) |
C4—C7 | 1.504 (2) | C12—H12 | 0.92 (2) |
C5—C6 | 1.446 (3) | C13—C14 | 1.382 (3) |
C7—C8 | 1.526 (3) | C14—H14 | 0.950 (19) |
C7—H6 | 0.97 (2) | ||
C1—N1—C5 | 115.24 (17) | C9—C8—H8 | 112.7 (14) |
N1—C1—C2 | 124.17 (19) | C7—C8—H8 | 109.1 (14) |
N1—C1—H1 | 115.9 (13) | C9—C8—H9 | 109.8 (15) |
C2—C1—H1 | 119.9 (13) | C7—C8—H9 | 108.9 (16) |
C1—C2—C3 | 119.2 (2) | H8—C8—H9 | 104.6 (19) |
C1—C2—H2 | 122.1 (14) | C14—C9—C10 | 118.50 (18) |
C3—C2—H2 | 118.6 (14) | C14—C9—C8 | 120.54 (19) |
C2—C3—C4 | 119.7 (2) | C10—C9—C8 | 120.9 (2) |
C2—C3—H3 | 120.1 (13) | C11—C10—C9 | 120.3 (2) |
C4—C3—H3 | 120.0 (13) | C11—C10—H10 | 116.1 (12) |
C5—C4—C3 | 115.82 (17) | C9—C10—H10 | 123.7 (12) |
C5—C4—C7 | 122.46 (16) | C12—C11—C10 | 120.9 (2) |
C3—C4—C7 | 121.72 (17) | C12—C11—H11 | 121.4 (16) |
N1—C5—C4 | 125.88 (17) | C10—C11—H11 | 117.7 (16) |
N1—C5—C6 | 114.91 (16) | C11—C12—C13 | 118.7 (2) |
C4—C5—C6 | 119.21 (15) | C11—C12—H12 | 121.2 (13) |
N2—C6—C5 | 177.5 (2) | C13—C12—H12 | 120.1 (14) |
C4—C7—C8 | 112.56 (15) | C12—C13—C14 | 121.2 (2) |
C4—C7—H6 | 107.4 (13) | C12—C13—Cl | 119.06 (15) |
C8—C7—H6 | 111.2 (13) | C14—C13—Cl | 119.70 (16) |
C4—C7—H7 | 108.3 (11) | C9—C14—C13 | 120.37 (19) |
C8—C7—H7 | 110.5 (10) | C9—C14—H14 | 120.6 (11) |
H6—C7—H7 | 106.7 (16) | C13—C14—H14 | 119.0 (11) |
C9—C8—C7 | 111.46 (16) | ||
C5—N1—C1—C2 | −0.4 (3) | C3—C4—C7—C8 | −88.4 (2) |
N1—C1—C2—C3 | 0.2 (3) | C4—C7—C8—C9 | 179.56 (18) |
C1—C2—C3—C4 | 0.3 (3) | C7—C8—C9—C14 | −92.8 (2) |
C2—C3—C4—C5 | −0.5 (3) | C7—C8—C9—C10 | 84.9 (2) |
C2—C3—C4—C7 | 178.98 (18) | C14—C9—C10—C11 | 0.5 (3) |
C1—N1—C5—C4 | 0.1 (3) | C8—C9—C10—C11 | −177.25 (19) |
C1—N1—C5—C6 | 179.82 (16) | C9—C10—C11—C12 | −0.6 (3) |
C3—C4—C5—N1 | 0.3 (3) | C10—C11—C12—C13 | 0.0 (3) |
C7—C4—C5—N1 | −179.15 (17) | C11—C12—C13—C14 | 0.6 (3) |
C3—C4—C5—C6 | −179.37 (16) | C11—C12—C13—Cl | 179.99 (16) |
C7—C4—C5—C6 | 1.1 (2) | C10—C9—C14—C13 | 0.1 (3) |
N1—C5—C6—N2 | −177 (100) | C8—C9—C14—C13 | 177.88 (16) |
C4—C5—C6—N2 | 3 (5) | C12—C13—C14—C9 | −0.7 (3) |
C5—C4—C7—C8 | 91.0 (2) | Cl—C13—C14—C9 | 179.93 (13) |
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