Crystal structure and Hirshfeld surface analysis of 8-aza­niumylquinolinium tetra­chlorido­zincate(II)

The organic–inorganic hybride salt (C₉H₁₀N₂)[ZnCl₄] consists of a planar 8-aza­niumylquinolinium dication and a tetra­hedral tetra­chlorido­zincate(II) dianion, held together by N—H...Cl and C—H...Cl hydrogen bonds, and π—π inter­actions.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 566 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.023
• wR factor = 0.065
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

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Alert level C
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ     Please Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          6 Note
PLAT012_ALERT_1_G N.O.K.   _shelx_res_checksum Found in CIF ......     Please Check
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00012 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00011 Ang.
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT794_ALERT_5_G Tentative Bond Valency for Zn1       (II)      .       1.94 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         13 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.5 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

   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
  11 ALERT level G = General information/check it is not something unexpected

   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
   2 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2020); cell refinement: CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

8-Azaniumylquinolinium tetrachloridozincate(II)

Crystal data

(C9H10N2)[ZnCl4]	F(000) = 704
Mr = 353.36	Dx = 1.840 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 7.52646 (6) Å	Cell parameters from 8253 reflections
b = 13.40703 (12) Å	θ = 3.3–71.4°
c = 12.65801 (11) Å	µ = 10.16 mm^−1
β = 92.8635 (8)°	T = 566 K
V = 1275.69 (2) Å^3	Block, pale yellow
Z = 4	0.24 × 0.21 × 0.15 mm

Data collection

Rigaku XtaLAB Synergy single source diffractometer with a HyPix3000 detector	2474 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2341 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.037
Detector resolution: 10.0000 pixels mm^-1	θmax = 71.4°, θmin = 4.8°
ω scans	h = −9→7
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2020)	k = −16→16
Tmin = 0.491, Tmax = 1.000	l = −15→15
11239 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.023	w = 1/[σ^2(Fo^2) + (0.0362P)^2 + 0.3283P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.065	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.32 e Å^−3
2474 reflections	Δρmin = −0.28 e Å^−3
162 parameters	Extinction correction: SHELXL (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
4 restraints	Extinction coefficient: 0.00359 (19)
Primary atom site location: dual

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
Zn1	0.92145 (3)	0.41694 (2)	0.17409 (2)	0.02862 (11)
Cl4	0.66523 (6)	0.36967 (4)	0.07893 (3)	0.03361 (13)
Cl1	0.84550 (6)	0.56627 (3)	0.24448 (4)	0.03547 (13)
Cl2	0.95542 (7)	0.31035 (3)	0.31521 (4)	0.03674 (14)
Cl3	1.16765 (6)	0.41294 (4)	0.08236 (4)	0.03691 (14)
N2	0.4715 (2)	0.39322 (11)	0.28755 (12)	0.0269 (3)
N1	0.4398 (2)	0.58098 (12)	0.17865 (12)	0.0296 (4)
C1	0.3676 (2)	0.56492 (13)	0.28262 (13)	0.0245 (4)
C8	0.3848 (2)	0.47086 (13)	0.33164 (13)	0.0228 (3)
C9	0.3120 (2)	0.45601 (14)	0.43180 (14)	0.0275 (4)
C4	0.2233 (2)	0.53608 (16)	0.47875 (15)	0.0340 (4)
H4	0.173175	0.526950	0.543724	0.041*
C2	0.2837 (2)	0.64101 (14)	0.33141 (16)	0.0320 (4)
H2A	0.274830	0.703201	0.299033	0.038*
C7	0.4940 (3)	0.30526 (14)	0.33447 (16)	0.0335 (4)
H7	0.556834	0.255296	0.301634	0.040*
C5	0.3326 (3)	0.36147 (16)	0.47933 (15)	0.0357 (4)
H5	0.282864	0.349307	0.543880	0.043*
C6	0.4245 (3)	0.28736 (16)	0.43198 (17)	0.0391 (5)
H6	0.440294	0.225711	0.464797	0.047*
C3	0.2103 (3)	0.62624 (16)	0.43029 (16)	0.0367 (5)
H3	0.152643	0.678533	0.462586	0.044*
H1A	0.5529 (15)	0.5639 (17)	0.179 (2)	0.042 (7)*
H1B	0.434 (3)	0.6446 (9)	0.160 (2)	0.056 (8)*
H1C	0.381 (3)	0.5492 (16)	0.1272 (14)	0.039 (6)*
H2	0.518 (3)	0.3968 (17)	0.2270 (11)	0.040 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.02863 (16)	0.02727 (16)	0.03004 (16)	0.00008 (9)	0.00209 (11)	−0.00273 (9)
Cl4	0.0300 (2)	0.0444 (3)	0.0265 (2)	−0.00244 (18)	0.00214 (17)	−0.00831 (18)
Cl1	0.0422 (3)	0.0237 (2)	0.0402 (3)	0.00109 (18)	−0.0005 (2)	−0.00495 (17)
Cl2	0.0478 (3)	0.0272 (2)	0.0354 (2)	0.00672 (19)	0.0037 (2)	0.00296 (17)
Cl3	0.0301 (2)	0.0450 (3)	0.0360 (3)	−0.00615 (18)	0.00597 (19)	−0.00603 (19)
N2	0.0301 (8)	0.0249 (7)	0.0258 (7)	−0.0017 (6)	0.0042 (6)	−0.0003 (6)
N1	0.0371 (9)	0.0273 (9)	0.0244 (8)	−0.0017 (7)	0.0025 (7)	0.0033 (6)
C1	0.0261 (8)	0.0257 (8)	0.0216 (8)	−0.0030 (7)	0.0006 (7)	0.0003 (6)
C8	0.0233 (8)	0.0249 (9)	0.0203 (8)	−0.0030 (7)	−0.0001 (6)	−0.0014 (6)
C9	0.0261 (8)	0.0333 (10)	0.0231 (8)	−0.0076 (7)	0.0009 (7)	0.0000 (7)
C4	0.0305 (9)	0.0469 (12)	0.0250 (9)	−0.0049 (8)	0.0058 (7)	−0.0074 (8)
C2	0.0340 (10)	0.0265 (9)	0.0352 (10)	0.0004 (7)	−0.0006 (8)	−0.0025 (7)
C7	0.0315 (10)	0.0242 (9)	0.0445 (11)	−0.0002 (7)	−0.0007 (8)	0.0014 (8)
C5	0.0367 (10)	0.0440 (11)	0.0266 (9)	−0.0092 (9)	0.0020 (8)	0.0100 (8)
C6	0.0394 (11)	0.0345 (10)	0.0428 (11)	−0.0054 (9)	−0.0041 (9)	0.0161 (9)
C3	0.0337 (10)	0.0391 (11)	0.0376 (11)	0.0012 (8)	0.0053 (8)	−0.0129 (9)

Geometric parameters (Å, º)

Zn1—Cl4	2.3108 (5)	C8—C9	1.420 (2)
Zn1—Cl1	2.2759 (5)	C9—C4	1.411 (3)
Zn1—Cl2	2.2919 (5)	C9—C5	1.408 (3)
Zn1—Cl3	2.2360 (5)	C4—H4	0.9300
N2—C8	1.362 (2)	C4—C3	1.357 (3)
N2—C7	1.327 (2)	C2—H2A	0.9300
N2—H2	0.860 (10)	C2—C3	1.407 (3)
N1—C1	1.464 (2)	C7—H7	0.9300
N1—H1A	0.882 (10)	C7—C6	1.385 (3)
N1—H1B	0.884 (10)	C5—H5	0.9300
N1—H1C	0.877 (10)	C5—C6	1.366 (3)
C1—C8	1.409 (2)	C6—H6	0.9300
C1—C2	1.364 (3)	C3—H3	0.9300
Cl1—Zn1—Cl4	103.058 (19)	C4—C9—C8	118.77 (17)
Cl1—Zn1—Cl2	105.30 (2)	C5—C9—C8	117.93 (18)
Cl2—Zn1—Cl4	107.04 (2)	C5—C9—C4	123.31 (17)
Cl3—Zn1—Cl4	114.479 (19)	C9—C4—H4	119.6
Cl3—Zn1—Cl1	117.08 (2)	C3—C4—C9	120.82 (18)
Cl3—Zn1—Cl2	109.07 (2)	C3—C4—H4	119.6
C8—N2—H2	123.2 (16)	C1—C2—H2A	119.7
C7—N2—C8	123.26 (16)	C1—C2—C3	120.58 (18)
C7—N2—H2	113.6 (16)	C3—C2—H2A	119.7
C1—N1—H1A	111.1 (17)	N2—C7—H7	119.8
C1—N1—H1B	111.1 (18)	N2—C7—C6	120.47 (18)
C1—N1—H1C	113.6 (16)	C6—C7—H7	119.8
H1A—N1—H1B	107 (2)	C9—C5—H5	119.5
H1A—N1—H1C	109 (2)	C6—C5—C9	120.96 (18)
H1B—N1—H1C	105 (2)	C6—C5—H5	119.5
C8—C1—N1	119.84 (15)	C7—C6—H6	120.4
C2—C1—N1	119.86 (16)	C5—C6—C7	119.13 (18)
C2—C1—C8	120.31 (17)	C5—C6—H6	120.4
N2—C8—C1	122.61 (15)	C4—C3—C2	120.33 (18)
N2—C8—C9	118.20 (16)	C4—C3—H3	119.8
C1—C8—C9	119.18 (16)	C2—C3—H3	119.8
N2—C8—C9—C4	179.45 (15)	C8—C9—C4—C3	−1.2 (3)
N2—C8—C9—C5	−0.5 (2)	C8—C9—C5—C6	2.0 (3)
N2—C7—C6—C5	0.0 (3)	C9—C4—C3—C2	0.7 (3)
N1—C1—C8—N2	1.9 (2)	C9—C5—C6—C7	−1.8 (3)
N1—C1—C8—C9	−179.12 (16)	C4—C9—C5—C6	−177.92 (18)
N1—C1—C2—C3	178.65 (17)	C2—C1—C8—N2	−178.25 (16)
C1—C8—C9—C4	0.5 (2)	C2—C1—C8—C9	0.7 (3)
C1—C8—C9—C5	−179.45 (16)	C7—N2—C8—C1	177.61 (17)
C1—C2—C3—C4	0.5 (3)	C7—N2—C8—C9	−1.3 (3)
C8—N2—C7—C6	1.6 (3)	C5—C9—C4—C3	178.74 (18)
C8—C1—C2—C3	−1.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1	0.88 (1)	2.31 (1)	3.1309 (16)	154 (2)
N1—H1B···Cl2^i	0.89 (1)	2.39 (1)	3.1747 (17)	148 (2)
N1—H1C···Cl3^ii	0.88 (2)	2.48 (2)	3.2415 (16)	145 (2)
N2—H2···Cl4	0.86 (2)	2.25 (2)	3.0958 (16)	166 (2)
C7—H7···Cl1^iii	0.93	2.71	3.584 (2)	157

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