4-[2-(4-Chloro­phen­yl)ethen­yl]-N-methyl­pyridinium tetra­phenyl­borate

Jin, D.; Zhang, F.; Zhang, Y.; Zhang, D.-C.

doi:10.1107/S160053680503151X

4-[2-(4-Chlorophenyl)ethenyl]-N-methylpyridinium tetraphenylborate

D. Jin, F. Zhang, Y. Zhang and D.-C. Zhang

The cation of the title compound, C₁₄H₁₃NCl⁺·B(C₆H₅)₄⁻, has a cis configuration at the C=C double bond. The pyridyl ring makes a dihedral angle of 53.8 (4)° with the benzene ring. Each cation is paired with another related by a twofold rotation through a π–π interaction and the cations also interact through a weak C—H

Cl interaction. The crystal structure is further stabilized by C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503151X/cf6452sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680503151X/cf6452Isup2.hkl Contains datablock I

CCDC reference: 289684

checkCIF report

Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.005 Å
R factor = 0.058
wR factor = 0.140
Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C10
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14B   ..  CL1     ..       3.07 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H4     ..  CG2     ..       3.20 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H36    ..  CG3     ..       3.15 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H34    ..  CG6     ..       3.19 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.35
           From the CIF: _reflns_number_total               5579
           Count of symmetry unique reflns         2978
           Completeness (_total/calc)            187.34%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2601
           Fraction of Friedel pairs measured     0.873
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

cis-4-[2–4-Chlorophenyl)ethenyl]-1-methylpyridium tetraphenylborate top

Crystal data top

C₁₄H₁₃ClN⁺·C₂₄H₂₀B⁻	F(000) = 4640
M_r = 549.91	D_x = 1.199 Mg m⁻³
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: F 2 -2d	Cell parameters from 10441 reflections
a = 33.358 (3) Å	θ = 3.2–25.3°
b = 37.815 (4) Å	µ = 0.15 mm⁻¹
c = 9.657 (1) Å	T = 193 K
V = 12182 (2) Å³	Block, yellow
Z = 16	0.35 × 0.27 × 0.25 mm

Data collection top

Rigaku Mercury diffractometer	5579 independent reflections
Radiation source: fine-focus sealed tube	4742 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.4°, θ_min = 3.2°
ω scans	h = −40→40
Absorption correction: multi-scan (Jacobson, 1998)	k = −45→45
T_min = 0.949, T_max = 0.963	l = −11→11
29974 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.058	H-atom parameters constrained
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.06P)² + 9.1861P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
5579 reflections	Δρ_max = 0.24 e Å⁻³
372 parameters	Δρ_min = −0.33 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 2601 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (10)

Special details top

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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.58416 (4)	−0.02873 (3)	0.99335 (14)	0.0916 (4)
N1	0.58941 (7)	0.17374 (6)	0.6469 (3)	0.0433 (6)
C1	0.55325 (9)	0.18896 (8)	0.6470 (3)	0.0504 (7)
H1	0.5478	0.2081	0.5863	0.060*
C2	0.52403 (9)	0.17698 (7)	0.7345 (3)	0.0484 (7)
H2	0.4984	0.1880	0.7326	0.058*
C3	0.53057 (8)	0.14926 (7)	0.8259 (3)	0.0448 (7)
C4	0.56936 (9)	0.13448 (8)	0.8242 (3)	0.0477 (7)
H4	0.5759	0.1157	0.8855	0.057*
C5	0.59760 (8)	0.14719 (7)	0.7343 (3)	0.0452 (7)
H5	0.6236	0.1370	0.7338	0.054*
C6	0.49892 (9)	0.13842 (9)	0.9202 (4)	0.0555 (8)
H6	0.4788	0.1557	0.9357	0.067*
C7	0.49355 (10)	0.10835 (9)	0.9881 (4)	0.0598 (8)
H7	0.4709	0.1080	1.0477	0.072*
C8	0.51713 (10)	0.07514 (8)	0.9863 (3)	0.0546 (8)
C9	0.52684 (15)	0.05825 (12)	1.1091 (4)	0.0886 (14)
H9	0.5189	0.0686	1.1945	0.106*
C10	0.54764 (18)	0.02708 (12)	1.1101 (5)	0.1008 (16)
H10	0.5547	0.0165	1.1958	0.121*
C11	0.55837 (11)	0.01113 (9)	0.9890 (4)	0.0624 (9)
C12	0.54825 (11)	0.02642 (9)	0.8662 (4)	0.0618 (9)
H12	0.5554	0.0152	0.7816	0.074*
C13	0.52758 (11)	0.05820 (9)	0.8641 (4)	0.0588 (8)
H13	0.5205	0.0685	0.7778	0.071*
C14	0.62061 (9)	0.18617 (8)	0.5498 (4)	0.0549 (8)
H14A	0.6410	0.1996	0.6008	0.082*
H14B	0.6084	0.2014	0.4795	0.082*
H14C	0.6332	0.1658	0.5047	0.082*
C15	0.61647 (8)	0.08834 (7)	0.3932 (3)	0.0427 (6)
C16	0.57959 (8)	0.10111 (8)	0.4416 (3)	0.0496 (7)
H16	0.5687	0.0913	0.5238	0.060*
C17	0.55820 (9)	0.12787 (9)	0.3731 (4)	0.0599 (9)
H17	0.5329	0.1353	0.4081	0.072*
C18	0.57354 (11)	0.14352 (9)	0.2555 (4)	0.0641 (10)
H18	0.5592	0.1618	0.2095	0.077*
C19	0.60979 (11)	0.13231 (9)	0.2065 (4)	0.0601 (9)
H19	0.6209	0.1429	0.1259	0.072*
C20	0.63046 (9)	0.10558 (8)	0.2739 (3)	0.0506 (8)
H20	0.6556	0.0985	0.2371	0.061*
C21	0.67822 (9)	0.04251 (7)	0.3771 (3)	0.0430 (7)
C22	0.66917 (9)	0.02854 (7)	0.2468 (3)	0.0494 (7)
H22	0.6422	0.0294	0.2156	0.059*
C23	0.69791 (11)	0.01349 (9)	0.1608 (4)	0.0579 (8)
H23	0.6904	0.0046	0.0726	0.069*
C24	0.73736 (10)	0.01152 (8)	0.2038 (4)	0.0574 (9)
H24	0.7571	0.0010	0.1461	0.069*
C25	0.74781 (10)	0.02503 (8)	0.3311 (3)	0.0519 (8)
H25	0.7749	0.0239	0.3612	0.062*
C26	0.71884 (9)	0.04027 (7)	0.4158 (3)	0.0462 (7)
H26	0.7268	0.0495	0.5031	0.055*
C27	0.61570 (9)	0.02315 (8)	0.5181 (3)	0.0500 (7)
C28	0.63379 (12)	−0.00327 (8)	0.5988 (3)	0.0617 (9)
H28	0.6611	−0.0003	0.6240	0.074*
C29	0.61431 (16)	−0.03337 (9)	0.6436 (5)	0.0805 (13)
H29	0.6275	−0.0501	0.7012	0.097*
C30	0.57504 (18)	−0.03859 (11)	0.6026 (5)	0.0943 (17)
H30	0.5610	−0.0591	0.6324	0.113*
C31	0.55605 (13)	−0.01436 (11)	0.5190 (5)	0.0850 (13)
H31	0.5295	−0.0186	0.4879	0.102*
C32	0.57611 (10)	0.01650 (9)	0.4799 (4)	0.0644 (9)
H32	0.5623	0.0335	0.4254	0.077*
C33	0.66003 (8)	0.07702 (7)	0.6162 (3)	0.0426 (7)
C34	0.64938 (10)	0.06842 (8)	0.7517 (3)	0.0524 (8)
H34	0.6311	0.0495	0.7664	0.063*
C35	0.66439 (12)	0.08635 (10)	0.8663 (4)	0.0662 (10)
H35	0.6566	0.0792	0.9566	0.079*
C36	0.69035 (12)	0.11439 (11)	0.8507 (4)	0.0718 (11)
H36	0.7003	0.1268	0.9291	0.086*
C37	0.70152 (9)	0.12409 (9)	0.7184 (4)	0.0629 (10)
H37	0.7195	0.1433	0.7054	0.076*
C38	0.68675 (9)	0.10602 (8)	0.6044 (4)	0.0515 (8)
H38	0.6949	0.1134	0.5146	0.062*
B1	0.64243 (10)	0.05815 (9)	0.4763 (4)	0.0424 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1096 (8)	0.0723 (6)	0.0929 (8)	0.0249 (6)	−0.0095 (7)	0.0048 (6)
N1	0.0424 (13)	0.0351 (12)	0.0523 (14)	0.0000 (10)	−0.0014 (12)	−0.0058 (11)
C1	0.0511 (18)	0.0416 (15)	0.0584 (19)	0.0042 (13)	−0.0091 (16)	−0.0039 (15)
C2	0.0426 (15)	0.0414 (16)	0.0612 (19)	0.0094 (12)	−0.0035 (15)	−0.0098 (15)
C3	0.0402 (15)	0.0428 (15)	0.0515 (17)	0.0002 (13)	0.0006 (13)	−0.0140 (14)
C4	0.0488 (17)	0.0397 (15)	0.0546 (18)	0.0035 (13)	−0.0043 (14)	−0.0012 (14)
C5	0.0382 (15)	0.0411 (15)	0.0563 (18)	0.0064 (12)	−0.0018 (14)	−0.0080 (15)
C6	0.0519 (17)	0.0529 (19)	0.062 (2)	0.0018 (15)	0.0071 (16)	−0.0104 (17)
C7	0.061 (2)	0.061 (2)	0.058 (2)	−0.0015 (15)	0.0171 (17)	−0.0103 (18)
C8	0.0606 (19)	0.0534 (18)	0.0498 (18)	−0.0048 (15)	0.0077 (16)	−0.0059 (16)
C9	0.135 (4)	0.080 (3)	0.050 (2)	0.025 (3)	0.001 (2)	−0.011 (2)
C10	0.161 (5)	0.081 (3)	0.061 (3)	0.021 (3)	−0.026 (3)	−0.001 (2)
C11	0.069 (2)	0.0559 (19)	0.062 (2)	0.0021 (16)	−0.0009 (19)	−0.0040 (19)
C12	0.076 (2)	0.054 (2)	0.056 (2)	0.0010 (17)	0.0081 (18)	−0.0062 (17)
C13	0.071 (2)	0.0549 (18)	0.050 (2)	0.0010 (17)	0.0043 (17)	−0.0046 (16)
C14	0.0508 (18)	0.0496 (18)	0.064 (2)	−0.0033 (14)	0.0065 (16)	0.0026 (16)
C15	0.0413 (14)	0.0440 (16)	0.0427 (16)	0.0019 (12)	0.0001 (13)	−0.0066 (13)
C16	0.0462 (16)	0.0442 (16)	0.0586 (19)	0.0010 (13)	0.0034 (15)	−0.0128 (14)
C17	0.0387 (16)	0.0529 (19)	0.088 (3)	0.0076 (14)	−0.0094 (18)	−0.0217 (19)
C18	0.067 (2)	0.0495 (19)	0.076 (3)	0.0122 (16)	−0.025 (2)	−0.0048 (19)
C19	0.071 (2)	0.0537 (18)	0.056 (2)	0.0066 (17)	−0.0119 (17)	0.0036 (16)
C20	0.0502 (17)	0.0532 (17)	0.0485 (19)	0.0084 (14)	−0.0013 (15)	0.0024 (15)
C21	0.0519 (17)	0.0374 (14)	0.0396 (15)	0.0059 (12)	0.0057 (13)	0.0031 (13)
C22	0.0552 (18)	0.0457 (16)	0.0475 (17)	0.0030 (13)	0.0086 (14)	−0.0027 (15)
C23	0.076 (2)	0.0527 (18)	0.0452 (17)	0.0040 (16)	0.0139 (17)	−0.0022 (15)
C24	0.064 (2)	0.0451 (17)	0.063 (2)	0.0120 (15)	0.0296 (17)	0.0041 (16)
C25	0.0486 (17)	0.0460 (17)	0.061 (2)	0.0114 (14)	0.0133 (15)	0.0067 (16)
C26	0.0531 (17)	0.0395 (15)	0.0460 (17)	0.0100 (12)	0.0076 (14)	0.0046 (13)
C27	0.0587 (18)	0.0434 (16)	0.0478 (17)	0.0032 (14)	0.0152 (15)	−0.0082 (14)
C28	0.089 (2)	0.0417 (17)	0.055 (2)	0.0128 (17)	0.0245 (19)	−0.0034 (16)
C29	0.119 (4)	0.0426 (19)	0.080 (3)	0.007 (2)	0.046 (3)	−0.0006 (19)
C30	0.126 (4)	0.044 (2)	0.113 (4)	−0.017 (2)	0.065 (3)	−0.012 (2)
C31	0.082 (3)	0.066 (3)	0.108 (3)	−0.022 (2)	0.032 (3)	−0.031 (3)
C32	0.066 (2)	0.0509 (18)	0.076 (2)	−0.0067 (16)	0.0185 (19)	−0.0194 (19)
C33	0.0421 (15)	0.0407 (15)	0.0450 (17)	0.0127 (12)	0.0046 (13)	0.0003 (13)
C34	0.068 (2)	0.0470 (17)	0.0423 (17)	0.0127 (15)	0.0003 (16)	0.0015 (14)
C35	0.094 (3)	0.061 (2)	0.0436 (19)	0.029 (2)	−0.0109 (18)	−0.0049 (17)
C36	0.072 (2)	0.071 (2)	0.072 (3)	0.033 (2)	−0.032 (2)	−0.022 (2)
C37	0.0423 (17)	0.059 (2)	0.087 (3)	0.0148 (15)	−0.0076 (18)	−0.020 (2)
C38	0.0425 (16)	0.0549 (18)	0.0571 (19)	0.0114 (14)	0.0043 (14)	−0.0076 (16)
B1	0.0442 (17)	0.0438 (17)	0.0392 (17)	0.0052 (14)	0.0068 (14)	0.0016 (15)

Geometric parameters (Å, º) top

Cl1—C11	1.736 (4)	C19—C20	1.386 (4)
N1—C1	1.337 (4)	C19—H19	0.950
N1—C5	1.340 (4)	C20—H20	0.950
N1—C14	1.478 (4)	C21—C22	1.398 (4)
C1—C2	1.367 (4)	C21—C26	1.408 (4)
C1—H1	0.950	C21—B1	1.641 (4)
C2—C3	1.387 (4)	C22—C23	1.390 (4)
C2—H2	0.950	C22—H22	0.950
C3—C4	1.410 (4)	C23—C24	1.382 (5)
C3—C6	1.453 (4)	C23—H23	0.950
C4—C5	1.368 (4)	C24—C25	1.376 (5)
C4—H4	0.950	C24—H24	0.950
C5—H5	0.950	C25—C26	1.392 (4)
C6—C7	1.325 (5)	C25—H25	0.950
C6—H6	0.950	C26—H26	0.950
C7—C8	1.482 (5)	C27—C32	1.394 (5)
C7—H7	0.950	C27—C28	1.403 (5)
C8—C9	1.385 (5)	C27—B1	1.646 (4)
C8—C13	1.387 (5)	C28—C29	1.380 (5)
C9—C10	1.368 (6)	C28—H28	0.950
C9—H9	0.950	C29—C30	1.383 (7)
C10—C11	1.363 (6)	C29—H29	0.950
C10—H10	0.950	C30—C31	1.376 (7)
C11—C12	1.362 (5)	C30—H30	0.950
C12—C13	1.386 (5)	C31—C32	1.397 (5)
C12—H12	0.950	C31—H31	0.950
C13—H13	0.950	C32—H32	0.950
C14—H14A	0.980	C33—C34	1.395 (4)
C14—H14B	0.980	C33—C38	1.418 (4)
C14—H14C	0.980	C33—B1	1.636 (5)
C15—C16	1.402 (4)	C34—C35	1.391 (5)
C15—C20	1.404 (4)	C34—H34	0.950
C15—B1	1.643 (4)	C35—C36	1.377 (6)
C16—C17	1.403 (5)	C35—H35	0.950
C16—H16	0.950	C36—C37	1.380 (6)
C17—C18	1.379 (5)	C36—H36	0.950
C17—H17	0.950	C37—C38	1.387 (5)
C18—C19	1.366 (5)	C37—H37	0.950
C18—H18	0.950	C38—H38	0.950

C1—N1—C5	120.4 (3)	C19—C20—C15	124.0 (3)
C1—N1—C14	119.9 (3)	C19—C20—H20	118.0
C5—N1—C14	119.6 (2)	C15—C20—H20	118.0
N1—C1—C2	120.1 (3)	C22—C21—C26	115.1 (3)
N1—C1—H1	120.0	C22—C21—B1	120.3 (3)
C2—C1—H1	120.0	C26—C21—B1	124.5 (3)
C1—C2—C3	122.1 (3)	C23—C22—C21	122.9 (3)
C1—C2—H2	119.0	C23—C22—H22	118.5
C3—C2—H2	119.0	C21—C22—H22	118.5
C2—C3—C4	115.9 (3)	C24—C23—C22	120.0 (3)
C2—C3—C6	119.8 (3)	C24—C23—H23	120.0
C4—C3—C6	124.2 (3)	C22—C23—H23	120.0
C5—C4—C3	120.0 (3)	C25—C24—C23	119.3 (3)
C5—C4—H4	120.0	C25—C24—H24	120.3
C3—C4—H4	120.0	C23—C24—H24	120.3
N1—C5—C4	121.5 (3)	C24—C25—C26	120.2 (3)
N1—C5—H5	119.3	C24—C25—H25	119.9
C4—C5—H5	119.3	C26—C25—H25	119.9
C7—C6—C3	130.6 (3)	C25—C26—C21	122.5 (3)
C7—C6—H6	114.7	C25—C26—H26	118.8
C3—C6—H6	114.7	C21—C26—H26	118.8
C6—C7—C8	130.5 (3)	C32—C27—C28	115.2 (3)
C6—C7—H7	114.7	C32—C27—B1	126.4 (3)
C8—C7—H7	114.7	C28—C27—B1	118.4 (3)
C9—C8—C13	117.2 (3)	C29—C28—C27	124.0 (4)
C9—C8—C7	120.3 (3)	C29—C28—H28	118.0
C13—C8—C7	122.3 (3)	C27—C28—H28	118.0
C10—C9—C8	121.4 (4)	C28—C29—C30	118.3 (4)
C10—C9—H9	119.3	C28—C29—H29	120.9
C8—C9—H9	119.3	C30—C29—H29	120.9
C11—C10—C9	120.6 (4)	C31—C30—C29	120.6 (4)
C11—C10—H10	119.7	C31—C30—H30	119.7
C9—C10—H10	119.7	C29—C30—H30	119.7
C12—C11—C10	119.6 (3)	C30—C31—C32	119.6 (4)
C12—C11—Cl1	120.8 (3)	C30—C31—H31	120.2
C10—C11—Cl1	119.6 (3)	C32—C31—H31	120.2
C11—C12—C13	120.3 (3)	C27—C32—C31	122.2 (4)
C11—C12—H12	119.9	C27—C32—H32	118.9
C13—C12—H12	119.9	C31—C32—H32	118.9
C12—C13—C8	120.9 (3)	C34—C33—C38	114.6 (3)
C12—C13—H13	119.6	C34—C33—B1	125.6 (3)
C8—C13—H13	119.6	C38—C33—B1	119.8 (3)
N1—C14—H14A	109.5	C35—C34—C33	122.8 (3)
N1—C14—H14B	109.5	C35—C34—H34	118.6
H14A—C14—H14B	109.5	C33—C34—H34	118.6
N1—C14—H14C	109.5	C36—C35—C34	121.0 (4)
H14A—C14—H14C	109.5	C36—C35—H35	119.5
H14B—C14—H14C	109.5	C34—C35—H35	119.5
C16—C15—C20	113.9 (3)	C35—C36—C37	118.4 (3)
C16—C15—B1	122.6 (3)	C35—C36—H36	120.8
C20—C15—B1	123.3 (2)	C37—C36—H36	120.8
C15—C16—C17	122.5 (3)	C36—C37—C38	120.5 (3)
C15—C16—H16	118.7	C36—C37—H37	119.7
C17—C16—H16	118.7	C38—C37—H37	119.7
C18—C17—C16	120.6 (3)	C37—C38—C33	122.7 (3)
C18—C17—H17	119.7	C37—C38—H38	118.6
C16—C17—H17	119.7	C33—C38—H38	118.6
C19—C18—C17	118.7 (3)	C33—B1—C21	112.2 (2)
C19—C18—H18	120.6	C33—B1—C15	106.8 (2)
C17—C18—H18	120.6	C21—B1—C15	110.4 (2)
C18—C19—C20	120.3 (3)	C33—B1—C27	110.1 (2)
C18—C19—H19	119.9	C21—B1—C27	104.3 (2)
C20—C19—H19	119.9	C15—B1—C27	113.1 (2)

C5—N1—C1—C2	−1.5 (4)	C32—C27—C28—C29	−2.5 (5)
C14—N1—C1—C2	178.5 (3)	B1—C27—C28—C29	178.2 (3)
N1—C1—C2—C3	0.5 (5)	C27—C28—C29—C30	2.5 (5)
C1—C2—C3—C4	0.7 (4)	C28—C29—C30—C31	0.1 (6)
C1—C2—C3—C6	177.7 (3)	C29—C30—C31—C32	−2.7 (6)
C2—C3—C4—C5	−1.1 (4)	C28—C27—C32—C31	−0.2 (5)
C6—C3—C4—C5	−178.0 (3)	B1—C27—C32—C31	179.1 (3)
C1—N1—C5—C4	1.1 (4)	C30—C31—C32—C27	2.7 (6)
C14—N1—C5—C4	−178.9 (3)	C38—C33—C34—C35	−1.3 (4)
C3—C4—C5—N1	0.2 (4)	B1—C33—C34—C35	−177.6 (3)
C2—C3—C6—C7	159.8 (4)	C33—C34—C35—C36	1.3 (5)
C4—C3—C6—C7	−23.4 (6)	C34—C35—C36—C37	−0.7 (5)
C3—C6—C7—C8	−2.9 (7)	C35—C36—C37—C38	0.2 (5)
C6—C7—C8—C9	134.5 (5)	C36—C37—C38—C33	−0.3 (4)
C6—C7—C8—C13	−50.7 (6)	C34—C33—C38—C37	0.8 (4)
C13—C8—C9—C10	3.2 (6)	B1—C33—C38—C37	177.4 (3)
C7—C8—C9—C10	178.2 (4)	C34—C33—B1—C21	−124.8 (3)
C8—C9—C10—C11	−2.0 (8)	C38—C33—B1—C21	59.1 (3)
C9—C10—C11—C12	0.0 (7)	C34—C33—B1—C15	114.1 (3)
C9—C10—C11—Cl1	−179.1 (4)	C38—C33—B1—C15	−62.1 (3)
C10—C11—C12—C13	0.8 (6)	C34—C33—B1—C27	−9.1 (4)
Cl1—C11—C12—C13	179.8 (3)	C38—C33—B1—C27	174.7 (2)
C11—C12—C13—C8	0.5 (6)	C22—C21—B1—C33	−173.8 (3)
C9—C8—C13—C12	−2.4 (5)	C26—C21—B1—C33	9.5 (4)
C7—C8—C13—C12	−177.4 (3)	C22—C21—B1—C15	−54.7 (3)
C20—C15—C16—C17	2.2 (4)	C26—C21—B1—C15	128.6 (3)
B1—C15—C16—C17	177.5 (3)	C22—C21—B1—C27	67.1 (3)
C15—C16—C17—C18	−1.8 (5)	C26—C21—B1—C27	−109.6 (3)
C16—C17—C18—C19	0.4 (5)	C16—C15—B1—C33	−70.7 (3)
C17—C18—C19—C20	0.3 (5)	C20—C15—B1—C33	104.2 (3)
C18—C19—C20—C15	0.2 (5)	C16—C15—B1—C21	167.1 (3)
C16—C15—C20—C19	−1.4 (4)	C20—C15—B1—C21	−18.0 (4)
B1—C15—C20—C19	−176.7 (3)	C16—C15—B1—C27	50.6 (4)
C26—C21—C22—C23	0.0 (4)	C20—C15—B1—C27	−134.5 (3)
B1—C21—C22—C23	−177.0 (3)	C32—C27—B1—C33	125.0 (3)
C21—C22—C23—C24	0.7 (5)	C28—C27—B1—C33	−55.8 (3)
C22—C23—C24—C25	−0.9 (5)	C32—C27—B1—C21	−114.4 (3)
C23—C24—C25—C26	0.5 (5)	C28—C27—B1—C21	64.8 (3)
C24—C25—C26—C21	0.3 (4)	C32—C27—B1—C15	5.6 (4)
C22—C21—C26—C25	−0.5 (4)	C28—C27—B1—C15	−175.2 (3)
B1—C21—C26—C25	176.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···Cl1ⁱ	0.98	3.07	3.577 (3)	113
C4—H4···Cg2	0.95	3.20	3.956 (2)	138
C36—H36···Cg3ⁱⁱ	0.95	3.15	3.997 (3)	150
C14—H14C···Cg4	0.98	2.86	3.529 (2)	126
C6—H6···Cg5ⁱⁱⁱ	0.95	2.82	3.663 (4)	148
C1—H1···Cg5^iv	0.95	2.65	3.505 (2)	150
C12—H12···Cg6	0.95	2.67	3.592 (3)	164
C34—H34···Cg6	0.95	3.19	3.887 (4)	132
C14—H14A···Cg6^iv	0.98	2.62	3.470 (2)	146
C5—H5···Cg7	0.95	2.32	3.237 (3)	162

Symmetry codes: (i) −x+5/4, y+1/4, z−3/4; (ii) x+1/4, −y+1/4, z+1/4; (iii) x−1/4, −y+1/4, z+3/4; (iv) −x+5/4, y+1/4, z+1/4.

Packing energies (PE) of some stilbazolium tetraphenylborates (kcal mol^-1) top

CSD refcode	Total PE	Space group	(a-a)%^a	(c-a)%^b	Substituent
QOBDEQ^b	-112.68	P2₁/c	22.63	53.16	4-N(CH₃)₂
WOCRAH^c	-122.95	P2₁/c	23.29	58.42	4-OCH₃
BOQKEX^d	-126.54	Cc	16.35	68.51	3,4-OCH₃
This study	-112.00	Fdd2	20.97	68.84	4-Cl

Notes: (a) (a-a)% is the percentage in the total PE for the anion–anion interaction and (c-a)% for the cation–anion interaction. References: (b) Li et al. (2000a), (c) Li et al. (2000b), (d) Zhang et al. (1999).

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4-[2-(4-Chloro­phen­yl)ethen­yl]-N-methyl­pyridinium tetra­phenyl­borate

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4-[2-(4-Chlorophenyl)ethenyl]-N-methylpyridinium tetraphenylborate