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The title imidoyl chloride, C16H8Cl4N2, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617002747/bt4044sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314617002747/bt4044Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314617002747/bt4044Isup3.cml
Supplementary material

CCDC reference: 1533438

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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
C16H8Cl4N2Z = 2
Mr = 370.04F(000) = 372
Triclinic, P1Dx = 1.639 Mg m3
a = 9.2595 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.9204 (15) ÅCell parameters from 9901 reflections
c = 10.1731 (15) Åθ = 2.3–29.9°
α = 64.259 (4)°µ = 0.78 mm1
β = 72.322 (5)°T = 100 K
γ = 64.093 (4)°Plate, light yellow
V = 749.6 (2) Å30.30 × 0.20 × 0.05 mm
Data collection top
Bruker APEXII CCD
diffractometer
3750 reflections with I > 2σ(I)
ω– and φ–scansRint = 0.033
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
θmax = 30.0°, θmin = 2.3°
Tmin = 0.689, Tmax = 0.746h = 1213
26858 measured reflectionsk = 1313
4335 independent reflectionsl = 1414
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-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 reflectionsΔρmax = 0.46 e Å3
199 parametersΔρmin = 0.20 e Å3
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
xyzUiso*/Ueq
Cl20.47318 (3)0.78291 (3)0.06212 (3)0.02002 (7)
Cl30.44918 (4)0.43177 (3)0.18302 (3)0.01907 (7)
Cl40.82948 (4)0.21042 (3)0.69589 (3)0.02329 (8)
Cl10.10737 (4)1.41289 (3)0.17857 (4)0.02702 (8)
N20.36407 (12)0.44659 (11)0.45370 (11)0.01588 (19)
N10.03955 (12)0.86631 (12)0.30708 (11)0.0181 (2)
C80.23627 (14)0.68779 (13)0.26551 (12)0.0139 (2)
C50.15842 (13)0.96888 (12)0.11060 (12)0.0136 (2)
C100.34979 (13)0.52050 (13)0.31946 (12)0.0140 (2)
C40.00070 (14)0.98888 (13)0.19243 (13)0.0154 (2)
C110.47579 (14)0.28773 (13)0.50743 (12)0.0144 (2)
C90.07433 (14)0.72394 (14)0.34052 (13)0.0172 (2)
H90.04690.63890.42040.021*
C120.64151 (15)0.25868 (14)0.47403 (13)0.0178 (2)
H120.68000.34370.41120.021*
C70.27708 (13)0.81186 (13)0.15223 (12)0.0132 (2)
C130.75057 (15)0.10521 (14)0.53263 (14)0.0186 (2)
H130.86390.08460.51090.022*
C10.06808 (15)1.24874 (13)0.03627 (13)0.0186 (2)
C20.08890 (15)1.27159 (14)0.04404 (14)0.0195 (2)
H20.17111.37490.02090.023*
C140.69239 (14)0.01764 (13)0.62317 (13)0.0166 (2)
C30.12176 (14)1.14356 (14)0.15572 (14)0.0186 (2)
H30.22781.15820.20940.022*
C60.19062 (14)1.10229 (13)0.00598 (13)0.0159 (2)
H60.29541.09020.06210.019*
C150.52756 (15)0.00998 (14)0.65689 (13)0.0191 (2)
H150.48970.07570.71840.023*
C160.41786 (15)0.16421 (13)0.59996 (13)0.0179 (2)
H160.30450.18510.62400.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl20.01386 (13)0.01335 (12)0.02513 (15)0.00307 (10)0.00064 (10)0.00410 (10)
Cl30.02500 (15)0.01218 (12)0.01400 (13)0.00016 (10)0.00392 (10)0.00510 (10)
Cl40.02391 (15)0.01314 (13)0.02437 (15)0.00239 (10)0.01131 (12)0.00309 (11)
Cl10.03162 (17)0.01036 (12)0.03095 (17)0.00513 (11)0.01023 (13)0.00125 (11)
N20.0173 (5)0.0109 (4)0.0146 (5)0.0015 (3)0.0033 (4)0.0031 (3)
N10.0156 (5)0.0163 (5)0.0182 (5)0.0027 (4)0.0028 (4)0.0051 (4)
C80.0153 (5)0.0107 (4)0.0132 (5)0.0019 (4)0.0037 (4)0.0038 (4)
C50.0160 (5)0.0104 (4)0.0139 (5)0.0016 (4)0.0061 (4)0.0042 (4)
C100.0137 (5)0.0113 (4)0.0143 (5)0.0025 (4)0.0013 (4)0.0047 (4)
C40.0151 (5)0.0138 (5)0.0161 (5)0.0013 (4)0.0059 (4)0.0056 (4)
C110.0181 (5)0.0107 (5)0.0109 (5)0.0010 (4)0.0043 (4)0.0033 (4)
C90.0164 (5)0.0152 (5)0.0153 (5)0.0042 (4)0.0016 (4)0.0031 (4)
C120.0198 (6)0.0131 (5)0.0183 (5)0.0052 (4)0.0042 (4)0.0034 (4)
C70.0123 (5)0.0117 (5)0.0139 (5)0.0016 (4)0.0033 (4)0.0048 (4)
C130.0159 (5)0.0167 (5)0.0212 (6)0.0026 (4)0.0059 (4)0.0061 (4)
C10.0254 (6)0.0106 (5)0.0193 (6)0.0038 (4)0.0105 (5)0.0025 (4)
C20.0206 (6)0.0123 (5)0.0239 (6)0.0021 (4)0.0117 (5)0.0072 (4)
C140.0207 (6)0.0113 (5)0.0143 (5)0.0002 (4)0.0081 (4)0.0036 (4)
C30.0154 (5)0.0163 (5)0.0218 (6)0.0009 (4)0.0065 (4)0.0087 (4)
C60.0179 (5)0.0117 (5)0.0168 (5)0.0035 (4)0.0050 (4)0.0040 (4)
C150.0228 (6)0.0128 (5)0.0160 (5)0.0050 (4)0.0033 (4)0.0012 (4)
C160.0172 (5)0.0142 (5)0.0160 (5)0.0028 (4)0.0024 (4)0.0027 (4)
Geometric parameters (Å, º) top
Cl2—C71.7268 (12)C11—C161.3933 (16)
Cl3—C101.7680 (11)C9—H90.9500
Cl4—C141.7424 (11)C12—C131.3881 (15)
Cl1—C11.7407 (12)C12—H120.9500
N2—C101.2551 (15)C13—C141.3861 (17)
N2—C111.4224 (13)C13—H130.9500
N1—C91.3121 (14)C1—C61.3698 (15)
N1—C41.3704 (15)C1—C21.4083 (18)
C8—C71.3768 (15)C2—C31.3678 (17)
C8—C91.4255 (16)C2—H20.9500
C8—C101.4817 (14)C14—C151.3858 (17)
C5—C61.4190 (15)C3—H30.9500
C5—C41.4202 (16)C6—H60.9500
C5—C71.4237 (14)C15—C161.3920 (15)
C4—C31.4209 (15)C15—H150.9500
C11—C121.3911 (17)C16—H160.9500
C10—N2—C11122.47 (10)C5—C7—Cl2118.57 (8)
C9—N1—C4117.52 (10)C14—C13—C12119.30 (11)
C7—C8—C9117.66 (10)C14—C13—H13120.4
C7—C8—C10124.91 (10)C12—C13—H13120.4
C9—C8—C10117.38 (10)C6—C1—C2122.32 (11)
C6—C5—C4119.79 (10)C6—C1—Cl1119.01 (10)
C6—C5—C7123.51 (10)C2—C1—Cl1118.67 (9)
C4—C5—C7116.71 (10)C3—C2—C1119.32 (10)
N2—C10—C8121.50 (10)C3—C2—H2120.3
N2—C10—Cl3123.61 (9)C1—C2—H2120.3
C8—C10—Cl3114.73 (8)C15—C14—C13121.29 (10)
N1—C4—C5123.25 (10)C15—C14—Cl4119.47 (9)
N1—C4—C3117.90 (11)C13—C14—Cl4119.25 (9)
C5—C4—C3118.85 (10)C2—C3—C4120.85 (11)
C12—C11—C16120.60 (10)C2—C3—H3119.6
C12—C11—N2119.73 (10)C4—C3—H3119.6
C16—C11—N2119.57 (10)C1—C6—C5118.87 (11)
N1—C9—C8124.64 (11)C1—C6—H6120.6
N1—C9—H9117.7C5—C6—H6120.6
C8—C9—H9117.7C14—C15—C16119.52 (11)
C13—C12—C11119.87 (11)C14—C15—H15120.2
C13—C12—H12120.1C16—C15—H15120.2
C11—C12—H12120.1C15—C16—C11119.41 (11)
C8—C7—C5120.21 (10)C15—C16—H16120.3
C8—C7—Cl2121.19 (8)C11—C16—H16120.3
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···N1i0.952.553.453 (2)159
Symmetry code: (i) x, y+1, z+1.
 

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