Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(E)-(2-phenyl­hydrazinyl­idene)meth­yl]quinoline

A new quinoline-based hydrazone compound, has been synthesized by a condensation reaction of 2-chloro-3-formyl­quinoline with phenyl­hydrazine. The quinoline ring system is essentially planar (r.m.s. deviation = 0.012 Å), and forms a dihedral angle of 8.46 (10)° with the phenyl ring substituent.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.029
• wR factor = 0.072
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N3       --H3N      .     Please Check
PLAT481_ALERT_4_C Long D...A H-Bond Reported N3       ..CG               4.06 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          5 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT-Plus (Bruker, 2016); data reduction: SAINT-Plus (Bruker, 2016); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

2-Chloro-3-[(E)-(2-phenylhydrazinylidene)methyl]quinoline

Crystal data

C16H12ClN3	F(000) = 584
Mr = 281.74	Dx = 1.377 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
a = 6.2114 (4) Å	Cell parameters from 2981 reflections
b = 19.4553 (11) Å	θ = 2.8–27.1°
c = 11.2520 (7) Å	µ = 0.27 mm^−1
β = 91.883 (2)°	T = 296 K
V = 1359.01 (14) Å^3	Block, brown
Z = 4	0.35 × 0.26 × 0.20 mm

Data collection

Bruker D8 VENTURE Super DUO diffractometer	2981 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2712 reflections with I > 2σ(I)
HELIOS mirror optics monochromator	Rint = 0.029
Detector resolution: 10.4167 pixels mm^-1	θmax = 27.1°, θmin = 2.8°
φ and ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −24→24
Tmin = 0.678, Tmax = 0.746	l = −14→14
21613 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.029	w = 1/[σ^2(Fo^2) + (0.0402P)^2 + 0.2303P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.072	(Δ/σ)max < 0.001
S = 1.03	Δρmax = 0.15 e Å^−3
2981 reflections	Δρmin = −0.14 e Å^−3
182 parameters	Extinction correction: (SHELXL2014; Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
2 restraints	Extinction coefficient: 0.0046 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack x determined using 1200 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.023 (15)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.50087 (11)	0.42496 (3)	0.50091 (7)	0.0554 (2)
N1	0.1727 (3)	0.34866 (11)	0.44617 (16)	0.0421 (4)
N2	0.6213 (3)	0.40817 (9)	0.12487 (17)	0.0419 (4)
N3	0.8016 (3)	0.43842 (10)	0.08642 (18)	0.0463 (5)
H3N	0.8814	0.4624	0.1345	0.056*
C1	0.3350 (3)	0.37935 (11)	0.39999 (19)	0.0393 (5)
C2	0.3882 (3)	0.37981 (11)	0.27845 (18)	0.0371 (5)
C3	0.2499 (4)	0.34346 (12)	0.20400 (18)	0.0395 (5)
H3	0.2744	0.3424	0.1229	0.047*
C4	0.0728 (4)	0.30794 (11)	0.24785 (18)	0.0379 (5)
C5	−0.0709 (4)	0.26905 (12)	0.1754 (2)	0.0470 (5)
H5	−0.0510	0.2665	0.0940	0.056*
C6	−0.2389 (4)	0.23516 (13)	0.2241 (2)	0.0511 (6)
H6	−0.3328	0.2096	0.1756	0.061*
C7	−0.2712 (5)	0.23870 (13)	0.3473 (3)	0.0544 (6)
H7	−0.3850	0.2149	0.3798	0.065*
C8	−0.1374 (4)	0.27659 (13)	0.4190 (2)	0.0498 (6)
H8	−0.1619	0.2794	0.4999	0.060*
C9	0.0384 (4)	0.31169 (11)	0.37146 (19)	0.0394 (5)
C10	0.5788 (4)	0.41442 (11)	0.2346 (2)	0.0421 (5)
H10	0.6671	0.4404	0.2855	0.051*
C11	0.8577 (4)	0.43052 (11)	−0.0315 (2)	0.0405 (5)
C12	0.7277 (4)	0.39628 (13)	−0.1134 (2)	0.0487 (5)
H12	0.5980	0.3773	−0.0905	0.058*
C13	0.7903 (5)	0.39014 (15)	−0.2298 (2)	0.0574 (7)
H13	0.7017	0.3670	−0.2847	0.069*
C14	0.9814 (5)	0.41769 (13)	−0.2655 (2)	0.0582 (7)
H14	1.0218	0.4137	−0.3441	0.070*
C15	1.1114 (5)	0.45108 (15)	−0.1835 (3)	0.0620 (7)
H15	1.2414	0.4697	−0.2067	0.074*
C16	1.0518 (5)	0.45757 (15)	−0.0663 (2)	0.0563 (7)
H16	1.1420	0.4800	−0.0113	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0558 (3)	0.0700 (4)	0.0398 (3)	−0.0078 (3)	−0.0075 (2)	−0.0099 (3)
N1	0.0487 (10)	0.0489 (10)	0.0288 (8)	−0.0018 (8)	0.0014 (8)	−0.0004 (7)
N2	0.0435 (11)	0.0417 (10)	0.0407 (10)	−0.0026 (8)	0.0042 (8)	0.0034 (8)
N3	0.0471 (11)	0.0510 (11)	0.0411 (10)	−0.0138 (9)	0.0049 (8)	−0.0024 (8)
C1	0.0438 (12)	0.0401 (11)	0.0336 (10)	0.0036 (9)	−0.0052 (9)	−0.0029 (9)
C2	0.0416 (12)	0.0352 (11)	0.0345 (11)	0.0044 (9)	0.0015 (9)	0.0009 (8)
C3	0.0474 (12)	0.0425 (12)	0.0290 (10)	0.0001 (9)	0.0052 (9)	−0.0021 (8)
C4	0.0453 (12)	0.0349 (10)	0.0335 (10)	0.0029 (9)	0.0025 (9)	0.0002 (8)
C5	0.0574 (14)	0.0469 (12)	0.0368 (12)	−0.0040 (11)	0.0024 (10)	−0.0047 (10)
C6	0.0566 (14)	0.0465 (14)	0.0499 (15)	−0.0112 (11)	−0.0021 (12)	−0.0065 (10)
C7	0.0541 (15)	0.0536 (14)	0.0561 (15)	−0.0123 (12)	0.0110 (12)	0.0013 (12)
C8	0.0575 (15)	0.0561 (15)	0.0361 (12)	−0.0054 (12)	0.0092 (10)	0.0025 (11)
C9	0.0459 (12)	0.0379 (11)	0.0343 (10)	0.0020 (9)	0.0016 (9)	0.0016 (8)
C10	0.0452 (12)	0.0426 (11)	0.0385 (11)	−0.0024 (10)	0.0011 (9)	−0.0009 (9)
C11	0.0454 (12)	0.0364 (12)	0.0401 (12)	−0.0003 (9)	0.0050 (9)	0.0038 (8)
C12	0.0464 (13)	0.0539 (13)	0.0457 (13)	−0.0040 (11)	−0.0004 (10)	0.0031 (10)
C13	0.0755 (19)	0.0575 (16)	0.0388 (13)	0.0056 (14)	−0.0042 (12)	0.0008 (11)
C14	0.084 (2)	0.0474 (14)	0.0441 (13)	0.0173 (14)	0.0182 (13)	0.0101 (11)
C15	0.0650 (18)	0.0549 (15)	0.0677 (18)	−0.0024 (13)	0.0277 (15)	0.0071 (13)
C16	0.0563 (15)	0.0560 (15)	0.0572 (16)	−0.0156 (12)	0.0113 (12)	−0.0022 (12)

Geometric parameters (Å, º)

Cl1—C1	1.750 (2)	C6—H6	0.9300
N1—C1	1.295 (3)	C7—C8	1.356 (4)
N1—C9	1.369 (3)	C7—H7	0.9300
N2—C10	1.277 (3)	C8—C9	1.408 (3)
N2—N3	1.349 (3)	C8—H8	0.9300
N3—C11	1.391 (3)	C10—H10	0.9300
N3—H3N	0.8600	C11—C12	1.377 (3)
C1—C2	1.417 (3)	C11—C16	1.384 (3)
C2—C3	1.376 (3)	C12—C13	1.384 (3)
C2—C10	1.461 (3)	C12—H12	0.9300
C3—C4	1.402 (3)	C13—C14	1.374 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.409 (3)	C14—C15	1.370 (5)
C4—C9	1.416 (3)	C14—H14	0.9300
C5—C6	1.365 (4)	C15—C16	1.387 (4)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.409 (4)	C16—H16	0.9300
C1—N1—C9	117.55 (18)	C7—C8—H8	119.8
C10—N2—N3	117.97 (19)	C9—C8—H8	119.8
N2—N3—C11	119.62 (19)	N1—C9—C8	119.1 (2)
N2—N3—H3N	120.2	N1—C9—C4	121.43 (19)
C11—N3—H3N	120.2	C8—C9—C4	119.5 (2)
N1—C1—C2	126.8 (2)	N2—C10—C2	118.6 (2)
N1—C1—Cl1	115.01 (16)	N2—C10—H10	120.7
C2—C1—Cl1	118.15 (17)	C2—C10—H10	120.7
C3—C2—C1	115.04 (19)	C12—C11—C16	119.4 (2)
C3—C2—C10	121.86 (19)	C12—C11—N3	122.1 (2)
C1—C2—C10	123.08 (19)	C16—C11—N3	118.4 (2)
C2—C3—C4	121.36 (19)	C11—C12—C13	119.9 (2)
C2—C3—H3	119.3	C11—C12—H12	120.0
C4—C3—H3	119.3	C13—C12—H12	120.0
C3—C4—C5	123.4 (2)	C14—C13—C12	121.0 (3)
C3—C4—C9	117.76 (19)	C14—C13—H13	119.5
C5—C4—C9	118.9 (2)	C12—C13—H13	119.5
C6—C5—C4	120.4 (2)	C15—C14—C13	118.9 (2)
C6—C5—H5	119.8	C15—C14—H14	120.5
C4—C5—H5	119.8	C13—C14—H14	120.5
C5—C6—C7	120.4 (2)	C14—C15—C16	120.9 (3)
C5—C6—H6	119.8	C14—C15—H15	119.5
C7—C6—H6	119.8	C16—C15—H15	119.5
C8—C7—C6	120.5 (2)	C11—C16—C15	119.8 (3)
C8—C7—H7	119.8	C11—C16—H16	120.1
C6—C7—H7	119.8	C15—C16—H16	120.1
C7—C8—C9	120.4 (2)

Hydrogen-bond geometry (Å, º)

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg^i	0.93	2.97	3.700 (3)	136
N3—H3N···Cg^ii	0.86	3.30	4.060	149

Symmetry codes: (i) x−3/2, −y+1/2, z+1/2; (ii) x, −y+1, z+1/2.