The title imidoyl chloride, C
16H
8Cl
4N
2, has formed accidentally as a side product during the synthesis of a quinolin-3-one derivative. The molecule is not flat [the dihedral angle between the 4,6-dichloroquinoline and the imidoyl chloride planes is 53.43 (5)°], preventing π-conjugation over the complete entity. In the crystal, C—H

N hydrogen bonding between a chlorophenyl C—H group and the quinoline N atom, as well as π–π stacking between neighbouring quinoline rings, consolidate the packing.
Supporting information
CCDC reference: 1533438
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.002 Å
- R factor = 0.025
- wR factor = 0.068
- Data-to-parameter ratio = 21.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.24 Report
Alert level G
PLAT012_ALERT_1_G N.O.K. _shelx_res_checksum found in CIF ........ Please Check
PLAT434_ALERT_2_G Short Inter HL..HL Contact Cl3 .. Cl3 .. 3.35 Ang.
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 15 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 15 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
4 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).
(
Z)-4,6-Dichloro-
N-(4-chlorophenyl)quinoline-3-carbimidoyl
chloride
top
Crystal data top
C16H8Cl4N2 | Z = 2 |
Mr = 370.04 | F(000) = 372 |
Triclinic, P1 | Dx = 1.639 Mg m−3 |
a = 9.2595 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.9204 (15) Å | Cell parameters from 9901 reflections |
c = 10.1731 (15) Å | θ = 2.3–29.9° |
α = 64.259 (4)° | µ = 0.78 mm−1 |
β = 72.322 (5)° | T = 100 K |
γ = 64.093 (4)° | Plate, light yellow |
V = 749.6 (2) Å3 | 0.30 × 0.20 × 0.05 mm |
Data collection top
Bruker APEXII CCD diffractometer | 3750 reflections with I > 2σ(I) |
ω– and φ–scans | Rint = 0.033 |
Absorption correction: multi-scan (SADABS; Bruker, 2015) | θmax = 30.0°, θmin = 2.3° |
Tmin = 0.689, Tmax = 0.746 | h = −12→13 |
26858 measured reflections | k = −13→13 |
4335 independent reflections | l = −14→14 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.0357P)2 + 0.2338P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
4335 reflections | Δρmax = 0.46 e Å−3 |
199 parameters | Δρmin = −0.20 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl2 | 0.47318 (3) | 0.78291 (3) | 0.06212 (3) | 0.02002 (7) | |
Cl3 | 0.44918 (4) | 0.43177 (3) | 0.18302 (3) | 0.01907 (7) | |
Cl4 | 0.82948 (4) | −0.21042 (3) | 0.69589 (3) | 0.02329 (8) | |
Cl1 | 0.10737 (4) | 1.41289 (3) | −0.17857 (4) | 0.02702 (8) | |
N2 | 0.36407 (12) | 0.44659 (11) | 0.45370 (11) | 0.01588 (19) | |
N1 | −0.03955 (12) | 0.86631 (12) | 0.30708 (11) | 0.0181 (2) | |
C8 | 0.23627 (14) | 0.68779 (13) | 0.26551 (12) | 0.0139 (2) | |
C5 | 0.15842 (13) | 0.96888 (12) | 0.11060 (12) | 0.0136 (2) | |
C10 | 0.34979 (13) | 0.52050 (13) | 0.31946 (12) | 0.0140 (2) | |
C4 | 0.00070 (14) | 0.98888 (13) | 0.19243 (13) | 0.0154 (2) | |
C11 | 0.47579 (14) | 0.28773 (13) | 0.50743 (12) | 0.0144 (2) | |
C9 | 0.07433 (14) | 0.72394 (14) | 0.34052 (13) | 0.0172 (2) | |
H9 | 0.0469 | 0.6389 | 0.4204 | 0.021* | |
C12 | 0.64151 (15) | 0.25868 (14) | 0.47403 (13) | 0.0178 (2) | |
H12 | 0.6800 | 0.3437 | 0.4112 | 0.021* | |
C7 | 0.27708 (13) | 0.81186 (13) | 0.15223 (12) | 0.0132 (2) | |
C13 | 0.75057 (15) | 0.10521 (14) | 0.53263 (14) | 0.0186 (2) | |
H13 | 0.8639 | 0.0846 | 0.5109 | 0.022* | |
C1 | 0.06808 (15) | 1.24874 (13) | −0.03627 (13) | 0.0186 (2) | |
C2 | −0.08890 (15) | 1.27159 (14) | 0.04404 (14) | 0.0195 (2) | |
H2 | −0.1711 | 1.3749 | 0.0209 | 0.023* | |
C14 | 0.69239 (14) | −0.01764 (13) | 0.62317 (13) | 0.0166 (2) | |
C3 | −0.12176 (14) | 1.14356 (14) | 0.15572 (14) | 0.0186 (2) | |
H3 | −0.2278 | 1.1582 | 0.2094 | 0.022* | |
C6 | 0.19062 (14) | 1.10229 (13) | −0.00598 (13) | 0.0159 (2) | |
H6 | 0.2954 | 1.0902 | −0.0621 | 0.019* | |
C15 | 0.52756 (15) | 0.00998 (14) | 0.65689 (13) | 0.0191 (2) | |
H15 | 0.4897 | −0.0757 | 0.7184 | 0.023* | |
C16 | 0.41786 (15) | 0.16421 (13) | 0.59996 (13) | 0.0179 (2) | |
H16 | 0.3045 | 0.1851 | 0.6240 | 0.021* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl2 | 0.01386 (13) | 0.01335 (12) | 0.02513 (15) | −0.00307 (10) | 0.00064 (10) | −0.00410 (10) |
Cl3 | 0.02500 (15) | 0.01218 (12) | 0.01400 (13) | −0.00016 (10) | −0.00392 (10) | −0.00510 (10) |
Cl4 | 0.02391 (15) | 0.01314 (13) | 0.02437 (15) | 0.00239 (10) | −0.01131 (12) | −0.00309 (11) |
Cl1 | 0.03162 (17) | 0.01036 (12) | 0.03095 (17) | −0.00513 (11) | −0.01023 (13) | 0.00125 (11) |
N2 | 0.0173 (5) | 0.0109 (4) | 0.0146 (5) | −0.0015 (3) | −0.0033 (4) | −0.0031 (3) |
N1 | 0.0156 (5) | 0.0163 (5) | 0.0182 (5) | −0.0027 (4) | −0.0028 (4) | −0.0051 (4) |
C8 | 0.0153 (5) | 0.0107 (4) | 0.0132 (5) | −0.0019 (4) | −0.0037 (4) | −0.0038 (4) |
C5 | 0.0160 (5) | 0.0104 (4) | 0.0139 (5) | −0.0016 (4) | −0.0061 (4) | −0.0042 (4) |
C10 | 0.0137 (5) | 0.0113 (4) | 0.0143 (5) | −0.0025 (4) | −0.0013 (4) | −0.0047 (4) |
C4 | 0.0151 (5) | 0.0138 (5) | 0.0161 (5) | −0.0013 (4) | −0.0059 (4) | −0.0056 (4) |
C11 | 0.0181 (5) | 0.0107 (5) | 0.0109 (5) | −0.0010 (4) | −0.0043 (4) | −0.0033 (4) |
C9 | 0.0164 (5) | 0.0152 (5) | 0.0153 (5) | −0.0042 (4) | −0.0016 (4) | −0.0031 (4) |
C12 | 0.0198 (6) | 0.0131 (5) | 0.0183 (5) | −0.0052 (4) | −0.0042 (4) | −0.0034 (4) |
C7 | 0.0123 (5) | 0.0117 (5) | 0.0139 (5) | −0.0016 (4) | −0.0033 (4) | −0.0048 (4) |
C13 | 0.0159 (5) | 0.0167 (5) | 0.0212 (6) | −0.0026 (4) | −0.0059 (4) | −0.0061 (4) |
C1 | 0.0254 (6) | 0.0106 (5) | 0.0193 (6) | −0.0038 (4) | −0.0105 (5) | −0.0025 (4) |
C2 | 0.0206 (6) | 0.0123 (5) | 0.0239 (6) | 0.0021 (4) | −0.0117 (5) | −0.0072 (4) |
C14 | 0.0207 (6) | 0.0113 (5) | 0.0143 (5) | 0.0002 (4) | −0.0081 (4) | −0.0036 (4) |
C3 | 0.0154 (5) | 0.0163 (5) | 0.0218 (6) | 0.0009 (4) | −0.0065 (4) | −0.0087 (4) |
C6 | 0.0179 (5) | 0.0117 (5) | 0.0168 (5) | −0.0035 (4) | −0.0050 (4) | −0.0040 (4) |
C15 | 0.0228 (6) | 0.0128 (5) | 0.0160 (5) | −0.0050 (4) | −0.0033 (4) | −0.0012 (4) |
C16 | 0.0172 (5) | 0.0142 (5) | 0.0160 (5) | −0.0028 (4) | −0.0024 (4) | −0.0027 (4) |
Geometric parameters (Å, º) top
Cl2—C7 | 1.7268 (12) | C11—C16 | 1.3933 (16) |
Cl3—C10 | 1.7680 (11) | C9—H9 | 0.9500 |
Cl4—C14 | 1.7424 (11) | C12—C13 | 1.3881 (15) |
Cl1—C1 | 1.7407 (12) | C12—H12 | 0.9500 |
N2—C10 | 1.2551 (15) | C13—C14 | 1.3861 (17) |
N2—C11 | 1.4224 (13) | C13—H13 | 0.9500 |
N1—C9 | 1.3121 (14) | C1—C6 | 1.3698 (15) |
N1—C4 | 1.3704 (15) | C1—C2 | 1.4083 (18) |
C8—C7 | 1.3768 (15) | C2—C3 | 1.3678 (17) |
C8—C9 | 1.4255 (16) | C2—H2 | 0.9500 |
C8—C10 | 1.4817 (14) | C14—C15 | 1.3858 (17) |
C5—C6 | 1.4190 (15) | C3—H3 | 0.9500 |
C5—C4 | 1.4202 (16) | C6—H6 | 0.9500 |
C5—C7 | 1.4237 (14) | C15—C16 | 1.3920 (15) |
C4—C3 | 1.4209 (15) | C15—H15 | 0.9500 |
C11—C12 | 1.3911 (17) | C16—H16 | 0.9500 |
| | | |
C10—N2—C11 | 122.47 (10) | C5—C7—Cl2 | 118.57 (8) |
C9—N1—C4 | 117.52 (10) | C14—C13—C12 | 119.30 (11) |
C7—C8—C9 | 117.66 (10) | C14—C13—H13 | 120.4 |
C7—C8—C10 | 124.91 (10) | C12—C13—H13 | 120.4 |
C9—C8—C10 | 117.38 (10) | C6—C1—C2 | 122.32 (11) |
C6—C5—C4 | 119.79 (10) | C6—C1—Cl1 | 119.01 (10) |
C6—C5—C7 | 123.51 (10) | C2—C1—Cl1 | 118.67 (9) |
C4—C5—C7 | 116.71 (10) | C3—C2—C1 | 119.32 (10) |
N2—C10—C8 | 121.50 (10) | C3—C2—H2 | 120.3 |
N2—C10—Cl3 | 123.61 (9) | C1—C2—H2 | 120.3 |
C8—C10—Cl3 | 114.73 (8) | C15—C14—C13 | 121.29 (10) |
N1—C4—C5 | 123.25 (10) | C15—C14—Cl4 | 119.47 (9) |
N1—C4—C3 | 117.90 (11) | C13—C14—Cl4 | 119.25 (9) |
C5—C4—C3 | 118.85 (10) | C2—C3—C4 | 120.85 (11) |
C12—C11—C16 | 120.60 (10) | C2—C3—H3 | 119.6 |
C12—C11—N2 | 119.73 (10) | C4—C3—H3 | 119.6 |
C16—C11—N2 | 119.57 (10) | C1—C6—C5 | 118.87 (11) |
N1—C9—C8 | 124.64 (11) | C1—C6—H6 | 120.6 |
N1—C9—H9 | 117.7 | C5—C6—H6 | 120.6 |
C8—C9—H9 | 117.7 | C14—C15—C16 | 119.52 (11) |
C13—C12—C11 | 119.87 (11) | C14—C15—H15 | 120.2 |
C13—C12—H12 | 120.1 | C16—C15—H15 | 120.2 |
C11—C12—H12 | 120.1 | C15—C16—C11 | 119.41 (11) |
C8—C7—C5 | 120.21 (10) | C15—C16—H16 | 120.3 |
C8—C7—Cl2 | 121.19 (8) | C11—C16—H16 | 120.3 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···N1i | 0.95 | 2.55 | 3.453 (2) | 159 |
Symmetry code: (i) −x, −y+1, −z+1. |