Structural comparison of three N-(4-halogenophen­yl)-N′-[1-(2-pyrid­yl)ethyl­idene]hydrazine hydro­chlorides

2-{1-[(4-Chloro­anilino)­methyl­idene]eth­yl}pyridinium chloride methanol solvate, C₁₃H₁₃ClN₃⁺·Cl⁻·CH₃OH, (I), crystallizes as discrete cations and anions, with one mol­ecule of methanol as solvent in the asymmetric unit. The N—C—C—N torsion angle in the cation indicates a cis conformation. The cations are located parallel to the (02) plane and are connected through hydrogen bonds by a methanol solvent mol­ecule and a chloride anion, forming zigzag chains in the direction of the b axis. The crystal structure of 2-{1-[(4-fluoro­anilino)methyl­idene]eth­yl}pyridinium chloride, C₁₃H₁₃FN₃⁺·Cl⁻, (II), con­tains just one anion and one cation in the asymmetric unit but no solvent. In contrast with (I), the N—C—C—N torsion angle in the cation corresponds with a trans conformation. The cations are located parallel to the (100) plane and are connected by hydrogen bonds to the chloride anions, forming zigzag chains in the direction of the b axis. In addition, the crystal packing is stabilized by weak π–π inter­actions between the pyridinium and benzene rings. The crystal of (II) is a nonmerohedral monoclinic twin which emulates an orthorhombic diffraction pattern. Twinning occurs via a twofold rotation about the c axis and the fractional contribution of the minor twin component refined to 0.324 (3). 2-{1-[(4-Fluoro­anilino)methyl­idene]eth­yl}pyridinium chloride methanol di­solvate, C₁₃H₁₃FN₃⁺·Cl⁻·2CH₃OH, (III), is a pseudopolymorph of (II). It crystallizes with two anions, two cations and four mol­ecules of methanol in the asymmetric unit. Two symmetry-equivalent cations are connected by hydrogen bonds to a chloride anion and a methanol solvent mol­ecule, forming a centrosymmetric dimer. A further methanol mol­ecule is hydrogen bonded to each chloride anion. These aggregates are connected by C—H...O contacts to form infinite chains. It is remarkable that the geometric structures of two compounds having two different formula units in their asymmetric units are essentially the same.

Computing details

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

(I) 2-{1-[(4-chloroanilino)methylidene]ethyl}pyridinium chloride methanol solvate

Crystal data

C13H13ClN^3+·Cl^−·CH4O	F(000) = 656
Mr = 314.21	Dx = 1.404 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 27165 reflections
a = 7.6715 (5) Å	θ = 2.5–29.8°
b = 16.0963 (10) Å	µ = 0.44 mm^−1
c = 12.0406 (8) Å	T = 173 K
β = 91.666 (5)°	Plate, yellow
V = 1486.18 (17) Å^3	0.38 × 0.24 × 0.08 mm
Z = 4

Data collection

Stoe IPDS II two-circle diffractometer	4284 independent reflections
Radiation source: fine-focus sealed tube	3625 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
ω scans	θmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −10→10
Tmin = 0.852, Tmax = 0.966	k = −22→21
24993 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0542P)^2 + 0.234P] where P = (Fo^2 + 2Fc^2)/3
4284 reflections	(Δ/σ)max < 0.001
195 parameters	Δρmax = 0.44 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
O1M	0.54425 (15)	0.47942 (6)	0.19018 (10)	0.0415 (2)
H1M	0.445 (3)	0.4919 (14)	0.1819 (18)	0.055 (6)*
C1M	0.6524 (2)	0.53177 (10)	0.12768 (14)	0.0463 (3)
H1A	0.6035	0.5880	0.1258	0.069*
H1B	0.6589	0.5103	0.0517	0.069*
H1C	0.7696	0.5332	0.1622	0.069*
Cl1	0.15567 (4)	0.54088 (2)	0.17191 (3)	0.03914 (9)
N1	0.64542 (14)	0.31183 (7)	0.23998 (9)	0.0303 (2)
H1	0.629 (3)	0.3635 (14)	0.2337 (16)	0.052 (5)*
N2	0.73493 (13)	0.27757 (6)	0.32529 (8)	0.02792 (19)
C2	0.81091 (15)	0.32529 (8)	0.39868 (10)	0.0286 (2)
C3	0.80979 (18)	0.41842 (8)	0.39609 (12)	0.0376 (3)
H3A	0.8777	0.4379	0.3335	0.056*
H3B	0.8615	0.4399	0.4657	0.056*
H3C	0.6894	0.4383	0.3873	0.056*
C11	0.55996 (14)	0.25978 (7)	0.16277 (10)	0.0278 (2)
C12	0.55353 (16)	0.17419 (8)	0.17739 (11)	0.0324 (2)
H12	0.6056	0.1497	0.2420	0.039*
C13	0.47108 (17)	0.12448 (8)	0.09766 (11)	0.0334 (2)
H13	0.4663	0.0660	0.1077	0.040*
C14	0.39583 (15)	0.16047 (8)	0.00342 (10)	0.0301 (2)
Cl14	0.29572 (4)	0.09690 (2)	−0.09736 (3)	0.03741 (9)
C15	0.40172 (17)	0.24567 (8)	−0.01256 (10)	0.0328 (2)
H15	0.3502	0.2698	−0.0776	0.039*
C16	0.48341 (17)	0.29545 (8)	0.06717 (10)	0.0322 (2)
H16	0.4875	0.3539	0.0569	0.039*
C21	0.90240 (15)	0.27999 (7)	0.48900 (10)	0.0284 (2)
N22	0.91829 (13)	0.19631 (7)	0.47922 (9)	0.0294 (2)
H22	0.875 (3)	0.1726 (12)	0.4175 (16)	0.048 (5)*
C23	0.99749 (17)	0.14786 (9)	0.55637 (11)	0.0345 (3)
H23	1.0048	0.0896	0.5450	0.041*
C24	1.06794 (18)	0.18271 (10)	0.65181 (11)	0.0391 (3)
H24	1.1255	0.1492	0.7065	0.047*
C25	1.05303 (18)	0.26772 (10)	0.66626 (11)	0.0395 (3)
H25	1.0995	0.2928	0.7321	0.047*
C26	0.97090 (16)	0.31677 (9)	0.58562 (10)	0.0343 (2)
H26	0.9614	0.3751	0.5962	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1M	0.0404 (5)	0.0293 (5)	0.0548 (6)	0.0057 (4)	−0.0013 (4)	0.0104 (4)
C1M	0.0538 (8)	0.0401 (8)	0.0450 (7)	0.0014 (6)	0.0044 (6)	0.0089 (6)
Cl1	0.03931 (16)	0.02899 (15)	0.04833 (18)	−0.00277 (11)	−0.01206 (13)	−0.00109 (12)
N1	0.0324 (5)	0.0232 (5)	0.0351 (5)	0.0033 (4)	−0.0057 (4)	0.0034 (4)
N2	0.0268 (4)	0.0262 (5)	0.0307 (4)	0.0029 (3)	−0.0015 (4)	0.0031 (4)
C2	0.0269 (5)	0.0255 (5)	0.0334 (5)	0.0023 (4)	0.0000 (4)	0.0003 (4)
C3	0.0390 (6)	0.0250 (6)	0.0483 (7)	0.0026 (5)	−0.0071 (5)	−0.0001 (5)
C11	0.0252 (5)	0.0268 (5)	0.0313 (5)	0.0031 (4)	−0.0004 (4)	0.0027 (4)
C12	0.0335 (6)	0.0287 (6)	0.0344 (5)	−0.0010 (4)	−0.0069 (4)	0.0072 (4)
C13	0.0354 (6)	0.0264 (5)	0.0378 (6)	−0.0009 (4)	−0.0060 (5)	0.0056 (4)
C14	0.0284 (5)	0.0313 (6)	0.0304 (5)	0.0006 (4)	−0.0009 (4)	0.0015 (4)
Cl14	0.04054 (17)	0.03700 (17)	0.03424 (15)	−0.00031 (12)	−0.00668 (11)	−0.00151 (11)
C15	0.0356 (6)	0.0325 (6)	0.0300 (5)	0.0038 (5)	−0.0033 (4)	0.0055 (4)
C16	0.0357 (6)	0.0256 (5)	0.0351 (6)	0.0039 (4)	−0.0029 (5)	0.0056 (4)
C21	0.0264 (5)	0.0277 (5)	0.0311 (5)	0.0005 (4)	0.0016 (4)	0.0004 (4)
N22	0.0295 (5)	0.0280 (5)	0.0307 (5)	0.0017 (4)	−0.0023 (4)	0.0023 (4)
C23	0.0327 (6)	0.0344 (6)	0.0362 (6)	0.0029 (5)	−0.0009 (5)	0.0090 (5)
C24	0.0348 (6)	0.0497 (8)	0.0326 (6)	0.0017 (5)	−0.0021 (5)	0.0100 (5)
C25	0.0371 (6)	0.0525 (8)	0.0288 (5)	−0.0054 (6)	−0.0020 (5)	−0.0008 (5)
C26	0.0331 (6)	0.0364 (6)	0.0335 (6)	−0.0022 (5)	0.0000 (5)	−0.0031 (5)

Geometric parameters (Å, º)

O1M—C1M	1.4145 (19)	C13—C14	1.3850 (16)
O1M—H1M	0.79 (2)	C13—H13	0.9500
C1M—H1A	0.9800	C14—C15	1.3859 (17)
C1M—H1B	0.9800	C14—Cl14	1.7478 (13)
C1M—H1C	0.9800	C15—C16	1.3862 (18)
N1—N2	1.3378 (13)	C15—H15	0.9500
N1—C11	1.4002 (16)	C16—H16	0.9500
N1—H1	0.84 (2)	C21—N22	1.3579 (15)
N2—C2	1.2964 (15)	C21—C26	1.3945 (17)
C2—C21	1.4706 (16)	N22—C23	1.3445 (15)
C2—C3	1.4994 (18)	N22—H22	0.89 (2)
C3—H3A	0.9800	C23—C24	1.3752 (19)
C3—H3B	0.9800	C23—H23	0.9500
C3—H3C	0.9800	C24—C25	1.385 (2)
C11—C12	1.3900 (17)	C24—H24	0.9500
C11—C16	1.4000 (16)	C25—C26	1.3883 (19)
C12—C13	1.3881 (18)	C25—H25	0.9500
C12—H12	0.9500	C26—H26	0.9500
C1M—O1M—H1M	111.1 (16)	C12—C13—H13	120.1
O1M—C1M—H1A	109.5	C13—C14—C15	120.87 (12)
O1M—C1M—H1B	109.5	C13—C14—Cl14	119.22 (10)
H1A—C1M—H1B	109.5	C15—C14—Cl14	119.89 (9)
O1M—C1M—H1C	109.5	C14—C15—C16	119.46 (11)
H1A—C1M—H1C	109.5	C14—C15—H15	120.3
H1B—C1M—H1C	109.5	C16—C15—H15	120.3
N2—N1—C11	118.89 (10)	C15—C16—C11	120.18 (11)
N2—N1—H1	123.1 (14)	C15—C16—H16	119.9
C11—N1—H1	117.7 (14)	C11—C16—H16	119.9
C2—N2—N1	119.32 (10)	N22—C21—C26	117.44 (11)
N2—C2—C21	113.94 (10)	N22—C21—C2	118.02 (11)
N2—C2—C3	125.17 (11)	C26—C21—C2	124.52 (11)
C21—C2—C3	120.89 (11)	C23—N22—C21	123.74 (11)
C2—C3—H3A	109.5	C23—N22—H22	118.6 (13)
C2—C3—H3B	109.5	C21—N22—H22	117.7 (13)
H3A—C3—H3B	109.5	N22—C23—C24	119.96 (13)
C2—C3—H3C	109.5	N22—C23—H23	120.0
H3A—C3—H3C	109.5	C24—C23—H23	120.0
H3B—C3—H3C	109.5	C23—C24—C25	118.44 (12)
C12—C11—C16	119.67 (11)	C23—C24—H24	120.8
C12—C11—N1	121.77 (11)	C25—C24—H24	120.8
C16—C11—N1	118.53 (11)	C24—C25—C26	120.77 (12)
C13—C12—C11	120.06 (11)	C24—C25—H25	119.6
C13—C12—H12	120.0	C26—C25—H25	119.6
C11—C12—H12	120.0	C25—C26—C21	119.63 (13)
C14—C13—C12	119.75 (11)	C25—C26—H26	120.2
C14—C13—H13	120.1	C21—C26—H26	120.2
C11—N1—N2—C2	−178.32 (10)	N1—C11—C16—C15	178.28 (11)
N1—N2—C2—C21	179.07 (10)	N2—C2—C21—N22	8.60 (15)
N1—N2—C2—C3	−0.84 (18)	C3—C2—C21—N22	−171.49 (11)
N2—N1—C11—C12	5.45 (17)	N2—C2—C21—C26	−169.87 (11)
N2—N1—C11—C16	−172.83 (10)	C3—C2—C21—C26	10.05 (18)
C16—C11—C12—C13	−0.20 (18)	C26—C21—N22—C23	−0.81 (17)
N1—C11—C12—C13	−178.47 (11)	C2—C21—N22—C23	−179.38 (11)
C11—C12—C13—C14	0.20 (19)	C21—N22—C23—C24	0.05 (19)
C12—C13—C14—C15	0.04 (19)	N22—C23—C24—C25	0.77 (19)
C12—C13—C14—Cl14	178.92 (10)	C23—C24—C25—C26	−0.8 (2)
C13—C14—C15—C16	−0.28 (19)	C24—C25—C26—C21	0.08 (19)
Cl14—C14—C15—C16	−179.15 (10)	N22—C21—C26—C25	0.72 (17)
C14—C15—C16—C11	0.28 (19)	C2—C21—C26—C25	179.19 (11)
C12—C11—C16—C15	−0.04 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1M	0.84 (2)	2.04 (2)	2.8656 (14)	165.9 (19)
O1M—H1M···Cl1	0.79 (2)	2.35 (2)	3.1425 (12)	174 (2)
N22—H22···Cl1^i	0.89 (2)	2.39 (2)	3.1356 (11)	141.8 (17)

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

(II) 2-{1-[(4-fluoroanilino)methylidene]ethyl}pyridinium chloride

Crystal data

C13H13FN3^+·Cl^−	F(000) = 552
Mr = 265.71	Dx = 1.411 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6800 reflections
a = 6.8522 (12) Å	θ = 3.5–25.1°
b = 11.5134 (16) Å	µ = 0.30 mm^−1
c = 15.856 (2) Å	T = 173 K
β = 90.048 (16)°	Plate, yellow
V = 1250.9 (3) Å^3	0.38 × 0.09 × 0.05 mm
Z = 4

Data collection

Stoe IPDS II two-circle diffractometer	2161 independent reflections
Radiation source: fine-focus sealed tube	1662 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.116
ω scans	θmax = 25.2°, θmin = 3.5°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −8→8
Tmin = 0.894, Tmax = 0.985	k = −13→13
6993 measured reflections	l = −16→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.163	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.1013P)^2] where P = (Fo^2 + 2Fc^2)/3
2161 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.63 e Å^−3

Special details

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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.2216 (2)	0.34607 (8)	0.83240 (8)	0.0438 (3)
N1	0.3060 (5)	0.6598 (3)	0.5108 (2)	0.0278 (7)
H1	0.3311	0.6943	0.5591	0.033*
N2	0.2655 (5)	0.5455 (2)	0.5080 (2)	0.0274 (7)
C2	0.2679 (6)	0.4873 (3)	0.5780 (3)	0.0274 (9)
C3	0.3159 (8)	0.5389 (4)	0.6620 (3)	0.0418 (11)
H3A	0.4197	0.5967	0.6554	0.063*
H3B	0.3601	0.4774	0.7003	0.063*
H3C	0.1995	0.5763	0.6854	0.063*
C11	0.3073 (6)	0.7226 (3)	0.4350 (3)	0.0272 (8)
C12	0.2687 (7)	0.6694 (3)	0.3575 (3)	0.0336 (9)
H12	0.2402	0.5887	0.3554	0.040*
C13	0.2719 (7)	0.7337 (4)	0.2843 (3)	0.0392 (10)
H13	0.2412	0.6988	0.2317	0.047*
C14	0.3204 (6)	0.8498 (4)	0.2891 (3)	0.0377 (10)
F14	0.3282 (5)	0.9128 (2)	0.2154 (2)	0.0545 (8)
C15	0.3614 (6)	0.9051 (4)	0.3636 (3)	0.0352 (10)
H15	0.3937	0.9854	0.3645	0.042*
C16	0.3545 (6)	0.8412 (3)	0.4377 (3)	0.0313 (9)
H16	0.3817	0.8776	0.4902	0.038*
C21	0.2221 (6)	0.3637 (3)	0.5681 (3)	0.0253 (8)
N22	0.2141 (5)	0.2941 (3)	0.6362 (2)	0.0315 (8)
H22	0.2338	0.3251	0.6862	0.038*
C23	0.1774 (6)	0.1792 (4)	0.6315 (3)	0.0351 (10)
H23	0.1754	0.1341	0.6817	0.042*
C24	0.1433 (6)	0.1270 (4)	0.5558 (3)	0.0373 (11)
H24	0.1173	0.0461	0.5528	0.045*
C25	0.1473 (6)	0.1948 (4)	0.4827 (3)	0.0355 (10)
H25	0.1241	0.1604	0.4292	0.043*
C26	0.1853 (6)	0.3123 (3)	0.4890 (3)	0.0280 (8)
H26	0.1866	0.3590	0.4396	0.034*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0652 (7)	0.0299 (5)	0.0362 (6)	0.0003 (5)	0.0012 (6)	0.0052 (5)
N1	0.0352 (17)	0.0241 (14)	0.0242 (17)	−0.0020 (14)	0.0029 (14)	0.0029 (13)
N2	0.0269 (16)	0.0239 (15)	0.0315 (19)	0.0010 (13)	0.0018 (14)	0.0005 (13)
C2	0.0264 (18)	0.0256 (18)	0.030 (2)	0.0009 (15)	0.0052 (17)	0.0006 (16)
C3	0.064 (3)	0.031 (2)	0.030 (2)	−0.004 (2)	−0.004 (3)	−0.0029 (19)
C11	0.0228 (17)	0.0270 (18)	0.032 (2)	0.0022 (15)	0.0053 (16)	0.0022 (16)
C12	0.039 (2)	0.0283 (19)	0.034 (2)	−0.0013 (18)	0.0006 (18)	0.0027 (16)
C13	0.042 (2)	0.038 (2)	0.037 (3)	0.003 (2)	−0.002 (2)	0.0027 (19)
C14	0.037 (2)	0.042 (2)	0.034 (3)	0.0005 (19)	0.002 (2)	0.017 (2)
F14	0.0655 (18)	0.0563 (17)	0.0417 (17)	−0.0007 (15)	0.0009 (15)	0.0267 (14)
C15	0.036 (2)	0.029 (2)	0.041 (3)	−0.0019 (17)	0.0041 (19)	0.0107 (18)
C16	0.0302 (19)	0.029 (2)	0.035 (3)	−0.0009 (16)	0.0014 (17)	0.0027 (18)
C21	0.0218 (16)	0.0274 (18)	0.027 (2)	0.0021 (15)	0.0042 (15)	0.0018 (15)
N22	0.0314 (16)	0.0347 (17)	0.0283 (18)	0.0011 (15)	0.0033 (15)	0.0041 (14)
C23	0.031 (2)	0.033 (2)	0.042 (3)	−0.0023 (17)	−0.0004 (19)	0.0135 (19)
C24	0.0313 (19)	0.0261 (19)	0.054 (3)	−0.0031 (16)	−0.002 (2)	0.009 (2)
C25	0.037 (2)	0.029 (2)	0.040 (3)	−0.0031 (17)	−0.003 (2)	−0.0046 (19)
C26	0.0319 (19)	0.0290 (18)	0.023 (2)	−0.0005 (15)	−0.0011 (16)	0.0022 (16)

Geometric parameters (Å, º)

N1—N2	1.345 (4)	C14—F14	1.376 (5)
N1—C11	1.402 (5)	C15—C16	1.387 (6)
N1—H1	0.8800	C15—H15	0.9500
N2—C2	1.297 (5)	C16—H16	0.9500
C2—C21	1.465 (5)	C21—N22	1.345 (5)
C2—C3	1.495 (6)	C21—C26	1.410 (6)
C3—H3A	0.9800	N22—C23	1.349 (5)
C3—H3B	0.9800	N22—H22	0.8800
C3—H3C	0.9800	C23—C24	1.363 (7)
C11—C12	1.398 (6)	C23—H23	0.9500
C11—C16	1.404 (6)	C24—C25	1.398 (7)
C12—C13	1.377 (6)	C24—H24	0.9500
C12—H12	0.9500	C25—C26	1.381 (6)
C13—C14	1.379 (6)	C25—H25	0.9500
C13—H13	0.9500	C26—H26	0.9500
C14—C15	1.372 (7)
N2—N1—C11	118.5 (3)	C14—C15—C16	118.5 (4)
N2—N1—H1	120.8	C14—C15—H15	120.8
C11—N1—H1	120.8	C16—C15—H15	120.8
C2—N2—N1	118.3 (3)	C15—C16—C11	119.9 (4)
N2—C2—C21	114.1 (3)	C15—C16—H16	120.1
N2—C2—C3	124.0 (3)	C11—C16—H16	120.1
C21—C2—C3	121.8 (4)	N22—C21—C26	117.2 (3)
C2—C3—H3A	109.5	N22—C21—C2	120.1 (4)
C2—C3—H3B	109.5	C26—C21—C2	122.7 (3)
H3A—C3—H3B	109.5	C21—N22—C23	123.2 (4)
C2—C3—H3C	109.5	C21—N22—H22	118.4
H3A—C3—H3C	109.5	C23—N22—H22	118.4
H3B—C3—H3C	109.5	N22—C23—C24	120.9 (4)
C12—C11—N1	121.7 (3)	N22—C23—H23	119.6
C12—C11—C16	119.7 (4)	C24—C23—H23	119.6
N1—C11—C16	118.5 (4)	C23—C24—C25	118.7 (4)
C13—C12—C11	120.2 (4)	C23—C24—H24	120.6
C13—C12—H12	119.9	C25—C24—H24	120.6
C11—C12—H12	119.9	C26—C25—C24	119.4 (4)
C12—C13—C14	118.6 (4)	C26—C25—H25	120.3
C12—C13—H13	120.7	C24—C25—H25	120.3
C14—C13—H13	120.7	C25—C26—C21	120.6 (4)
C15—C14—F14	118.6 (4)	C25—C26—H26	119.7
C15—C14—C13	123.1 (4)	C21—C26—H26	119.7
F14—C14—C13	118.3 (4)
C11—N1—N2—C2	178.8 (4)	N1—C11—C16—C15	178.6 (4)
N1—N2—C2—C21	−179.9 (3)	N2—C2—C21—N22	−178.1 (4)
N1—N2—C2—C3	−1.0 (6)	C3—C2—C21—N22	2.9 (6)
N2—N1—C11—C12	−0.3 (6)	N2—C2—C21—C26	2.0 (5)
N2—N1—C11—C16	−178.4 (3)	C3—C2—C21—C26	−177.0 (4)
N1—C11—C12—C13	−179.8 (4)	C26—C21—N22—C23	1.5 (6)
C16—C11—C12—C13	−1.7 (7)	C2—C21—N22—C23	−178.4 (4)
C11—C12—C13—C14	2.2 (7)	C21—N22—C23—C24	−0.9 (6)
C12—C13—C14—C15	−1.6 (7)	N22—C23—C24—C25	0.1 (6)
C12—C13—C14—F14	178.3 (4)	C23—C24—C25—C26	−0.1 (6)
F14—C14—C15—C16	−179.6 (4)	C24—C25—C26—C21	0.7 (6)
C13—C14—C15—C16	0.3 (7)	N22—C21—C26—C25	−1.4 (6)
C14—C15—C16—C11	0.3 (6)	C2—C21—C26—C25	178.4 (4)
C12—C11—C16—C15	0.4 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N22—H22···Cl1	0.88	2.33	3.168 (4)	159
N1—H1···Cl1^i	0.88	2.48	3.289 (4)	153

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

(III) 2-{1-[(4-Fluoroanilino)methylidene]ethyl}pyridinium chloride methanol disolvate

Crystal data

C13H13FN3^+·Cl^−·2CH4O	Z = 4
Mr = 329.80	F(000) = 696
Triclinic, P1	Dx = 1.289 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0088 (8) Å	Cell parameters from 12810 reflections
b = 11.7258 (14) Å	θ = 2.2–27.2°
c = 21.843 (2) Å	µ = 0.25 mm^−1
α = 96.321 (9)°	T = 173 K
β = 92.066 (9)°	Plate, yellow
γ = 107.247 (9)°	0.42 × 0.26 × 0.14 mm
V = 1699.6 (3) Å^3

Data collection

Stoe IPDS II two-circle diffractometer	7158 independent reflections
Radiation source: fine-focus sealed tube	4239 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ω scans	θmax = 27.2°, θmin = 2.5°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −8→9
Tmin = 0.904, Tmax = 0.967	k = −15→15
21250 measured reflections	l = −27→27

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.058	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ^2(Fo^2) + (0.020P)^2] where P = (Fo^2 + 2Fc^2)/3
7158 reflections	(Δ/σ)max = 0.001
435 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.14 e Å^−3

Special details

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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.06824 (7)	0.39520 (4)	0.835725 (17)	0.04234 (11)
Cl2	0.70783 (7)	0.36712 (4)	0.328298 (17)	0.04196 (11)
N1	0.7276 (2)	0.48488 (11)	0.94796 (6)	0.0351 (3)
H1	0.683 (3)	0.4436 (15)	0.9145 (8)	0.040 (5)*
N2	0.69117 (19)	0.43426 (11)	0.99985 (5)	0.0315 (3)
C2	0.5986 (2)	0.31994 (13)	0.99561 (6)	0.0326 (3)
C3	0.5307 (3)	0.23792 (14)	0.93617 (7)	0.0449 (4)
H3A	0.6418	0.2494	0.9092	0.067*
H3B	0.4189	0.2566	0.9157	0.067*
H3C	0.4870	0.1541	0.9448	0.067*
C11	0.8345 (2)	0.60680 (13)	0.95032 (7)	0.0318 (3)
C12	0.9020 (2)	0.68115 (13)	1.00578 (7)	0.0357 (4)
H12	0.8760	0.6496	1.0439	0.043*
C13	1.0078 (2)	0.80191 (14)	1.00527 (7)	0.0385 (4)
H13	1.0542	0.8538	1.0428	0.046*
C14	1.0437 (2)	0.84435 (13)	0.94967 (7)	0.0371 (4)
F14	1.14943 (15)	0.96342 (8)	0.94906 (4)	0.0510 (3)
C15	0.9790 (2)	0.77361 (13)	0.89407 (7)	0.0372 (4)
H15	1.0061	0.8063	0.8563	0.045*
C16	0.8734 (2)	0.65336 (14)	0.89447 (7)	0.0358 (4)
H16	0.8273	0.6025	0.8566	0.043*
C21	0.5654 (2)	0.27333 (13)	1.05501 (6)	0.0322 (3)
N22	0.6445 (2)	0.34944 (12)	1.10693 (6)	0.0331 (3)
H22	0.722 (2)	0.4254 (15)	1.1036 (7)	0.036 (4)*
C23	0.6243 (3)	0.31773 (14)	1.16431 (7)	0.0389 (4)
H23	0.6825	0.3753	1.1992	0.047*
C24	0.5195 (3)	0.20214 (15)	1.17223 (7)	0.0416 (4)
H24	0.5048	0.1784	1.2124	0.050*
C25	0.4355 (3)	0.12077 (14)	1.12061 (7)	0.0421 (4)
H25	0.3617	0.0404	1.1253	0.051*
C26	0.4581 (2)	0.15534 (14)	1.06253 (7)	0.0376 (4)
H26	0.4003	0.0987	1.0273	0.045*
N1A	0.2446 (2)	0.48192 (11)	0.45536 (6)	0.0343 (3)
H1A	0.226 (2)	0.4372 (14)	0.4218 (8)	0.038 (5)*
N2A	0.18085 (19)	0.43786 (11)	0.50735 (5)	0.0325 (3)
C2A	0.0736 (2)	0.32604 (13)	0.50393 (7)	0.0330 (3)
C3A	0.0126 (3)	0.24187 (14)	0.44479 (7)	0.0406 (4)
H3A1	−0.0501	0.2788	0.4149	0.061*
H3A2	−0.0831	0.1661	0.4529	0.061*
H3A3	0.1311	0.2258	0.4280	0.061*
C11A	0.3642 (2)	0.60216 (13)	0.45792 (7)	0.0319 (3)
C12A	0.4080 (2)	0.68097 (13)	0.51257 (7)	0.0348 (4)
H12A	0.3597	0.6536	0.5501	0.042*
C13A	0.5222 (3)	0.79955 (14)	0.51206 (7)	0.0395 (4)
H13A	0.5529	0.8543	0.5490	0.047*
C14A	0.5899 (3)	0.83650 (13)	0.45735 (7)	0.0396 (4)
F14A	0.70313 (17)	0.95385 (8)	0.45658 (4)	0.0582 (3)
C15A	0.5499 (2)	0.76067 (14)	0.40260 (7)	0.0381 (4)
H15A	0.5998	0.7890	0.3654	0.046*
C16A	0.4356 (2)	0.64250 (13)	0.40288 (7)	0.0351 (4)
H16A	0.4055	0.5886	0.3656	0.042*
C21A	0.0143 (2)	0.28592 (13)	0.56329 (6)	0.0322 (3)
N22A	0.0658 (2)	0.36833 (12)	0.61436 (6)	0.0333 (3)
H22A	0.135 (3)	0.4436 (16)	0.6114 (8)	0.043 (5)*
C23A	0.0209 (2)	0.34280 (14)	0.67159 (7)	0.0382 (4)
H23A	0.0601	0.4047	0.7056	0.046*
C24A	−0.0813 (3)	0.22747 (15)	0.68089 (7)	0.0434 (4)
H24A	−0.1134	0.2083	0.7212	0.052*
C25A	−0.1369 (3)	0.13953 (15)	0.63032 (7)	0.0439 (4)
H25A	−0.2075	0.0590	0.6358	0.053*
C26A	−0.0901 (3)	0.16818 (14)	0.57208 (7)	0.0387 (4)
H26A	−0.1293	0.1073	0.5376	0.046*
O1M	0.5121 (2)	0.40944 (12)	0.82663 (5)	0.0540 (3)
H1M	0.377 (4)	0.393 (2)	0.8300 (11)	0.089 (8)*
C1M	0.5448 (4)	0.3692 (3)	0.76751 (9)	0.0896 (8)
H1M1	0.4621	0.3944	0.7379	0.134*
H1M2	0.5090	0.2811	0.7623	0.134*
H1M3	0.6865	0.4032	0.7603	0.134*
O2M	−0.1240 (3)	0.11921 (14)	0.83089 (7)	0.0780 (5)
H2M	−0.070 (4)	0.200 (3)	0.8328 (12)	0.108 (9)*
C2M	0.0255 (4)	0.0708 (2)	0.80911 (11)	0.0791 (7)
H2M1	0.1195	0.1295	0.7873	0.119*
H2M2	−0.0364	−0.0030	0.7808	0.119*
H2M3	0.0976	0.0522	0.8441	0.119*
O3M	0.2720 (2)	0.36917 (12)	0.33337 (5)	0.0551 (3)
H3M	0.396 (4)	0.3716 (19)	0.3358 (10)	0.074 (7)*
C3M	0.1617 (3)	0.2922 (2)	0.28236 (10)	0.0819 (8)
H3MB	0.0226	0.2936	0.2818	0.123*
H3MC	0.1654	0.2100	0.2852	0.123*
H3MD	0.2200	0.3189	0.2443	0.123*
O4M	0.4818 (3)	0.09243 (15)	0.32573 (8)	0.0804 (5)
H4M	0.533 (4)	0.168 (2)	0.3318 (11)	0.092 (8)*
C4M	0.6154 (4)	0.0320 (2)	0.30259 (11)	0.0806 (7)
H4M1	0.6922	0.0761	0.2714	0.121*
H4M2	0.5397	−0.0495	0.2838	0.121*
H4M3	0.7074	0.0274	0.3365	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0473 (3)	0.0388 (2)	0.0346 (2)	0.00589 (19)	−0.00038 (18)	−0.00106 (16)
Cl2	0.0474 (3)	0.0388 (2)	0.03419 (19)	0.00654 (19)	0.00114 (18)	−0.00019 (16)
N1	0.0409 (9)	0.0336 (7)	0.0264 (6)	0.0058 (6)	0.0008 (6)	0.0003 (6)
N2	0.0313 (7)	0.0336 (7)	0.0297 (6)	0.0101 (6)	0.0027 (5)	0.0031 (5)
C2	0.0317 (9)	0.0340 (8)	0.0303 (7)	0.0083 (7)	0.0021 (7)	0.0014 (6)
C3	0.0565 (12)	0.0363 (9)	0.0345 (8)	0.0058 (8)	0.0011 (8)	−0.0032 (7)
C11	0.0307 (9)	0.0327 (8)	0.0319 (7)	0.0105 (7)	0.0005 (7)	0.0011 (6)
C12	0.0394 (10)	0.0366 (8)	0.0316 (7)	0.0127 (7)	0.0022 (7)	0.0030 (6)
C13	0.0392 (10)	0.0371 (9)	0.0367 (8)	0.0110 (8)	−0.0031 (7)	−0.0031 (7)
C14	0.0341 (9)	0.0295 (8)	0.0458 (9)	0.0077 (7)	0.0002 (7)	0.0033 (7)
F14	0.0584 (7)	0.0320 (5)	0.0549 (6)	0.0028 (5)	−0.0002 (5)	0.0040 (4)
C15	0.0397 (10)	0.0374 (9)	0.0354 (8)	0.0117 (8)	0.0038 (7)	0.0074 (7)
C16	0.0372 (9)	0.0377 (8)	0.0311 (8)	0.0110 (7)	−0.0001 (7)	−0.0004 (6)
C21	0.0290 (9)	0.0336 (8)	0.0325 (7)	0.0093 (7)	0.0001 (6)	−0.0009 (6)
N22	0.0352 (8)	0.0302 (7)	0.0319 (7)	0.0071 (6)	0.0024 (6)	0.0034 (5)
C23	0.0443 (11)	0.0412 (9)	0.0305 (8)	0.0130 (8)	0.0009 (7)	0.0021 (7)
C24	0.0480 (11)	0.0427 (9)	0.0352 (8)	0.0135 (8)	0.0049 (8)	0.0087 (7)
C25	0.0429 (10)	0.0347 (8)	0.0469 (9)	0.0074 (8)	0.0062 (8)	0.0084 (7)
C26	0.0366 (10)	0.0339 (8)	0.0383 (8)	0.0064 (7)	0.0018 (7)	−0.0005 (7)
N1A	0.0408 (8)	0.0328 (7)	0.0259 (6)	0.0070 (6)	0.0032 (6)	0.0009 (6)
N2A	0.0344 (8)	0.0350 (7)	0.0280 (6)	0.0101 (6)	0.0025 (6)	0.0054 (5)
C2A	0.0313 (9)	0.0354 (8)	0.0309 (7)	0.0090 (7)	−0.0007 (7)	0.0027 (6)
C3A	0.0455 (10)	0.0397 (9)	0.0310 (8)	0.0063 (8)	−0.0011 (7)	0.0002 (7)
C11A	0.0310 (9)	0.0336 (8)	0.0308 (7)	0.0098 (7)	−0.0010 (7)	0.0042 (6)
C12A	0.0356 (9)	0.0393 (8)	0.0287 (7)	0.0113 (7)	0.0009 (7)	0.0018 (6)
C13A	0.0431 (10)	0.0381 (9)	0.0337 (8)	0.0096 (8)	−0.0016 (7)	−0.0022 (7)
C14A	0.0406 (10)	0.0306 (8)	0.0418 (9)	0.0031 (7)	−0.0009 (8)	0.0034 (7)
F14A	0.0738 (8)	0.0352 (5)	0.0507 (6)	−0.0054 (5)	0.0041 (5)	0.0027 (4)
C15A	0.0420 (10)	0.0398 (9)	0.0314 (8)	0.0089 (8)	0.0051 (7)	0.0085 (7)
C16A	0.0382 (10)	0.0364 (8)	0.0291 (7)	0.0106 (7)	−0.0004 (7)	0.0007 (6)
C21A	0.0296 (9)	0.0354 (8)	0.0304 (7)	0.0093 (7)	−0.0016 (6)	0.0018 (6)
N22A	0.0347 (8)	0.0329 (7)	0.0287 (6)	0.0054 (6)	−0.0010 (6)	0.0027 (5)
C23A	0.0396 (10)	0.0437 (9)	0.0283 (8)	0.0086 (8)	−0.0008 (7)	0.0032 (7)
C24A	0.0474 (11)	0.0477 (10)	0.0319 (8)	0.0085 (8)	0.0008 (8)	0.0093 (7)
C25A	0.0474 (11)	0.0383 (9)	0.0419 (9)	0.0053 (8)	0.0007 (8)	0.0101 (7)
C26A	0.0411 (10)	0.0342 (8)	0.0364 (8)	0.0059 (7)	−0.0006 (7)	0.0022 (7)
O1M	0.0491 (9)	0.0727 (9)	0.0365 (6)	0.0180 (7)	−0.0033 (6)	−0.0053 (6)
C1M	0.0633 (16)	0.151 (2)	0.0451 (11)	0.0294 (16)	0.0024 (11)	−0.0196 (14)
O2M	0.1015 (14)	0.0438 (9)	0.0763 (10)	0.0011 (9)	0.0310 (9)	0.0060 (7)
C2M	0.119 (2)	0.0541 (13)	0.0682 (14)	0.0286 (14)	0.0057 (14)	0.0166 (11)
O3M	0.0476 (9)	0.0655 (8)	0.0425 (7)	0.0097 (7)	0.0049 (6)	−0.0136 (6)
C3M	0.0587 (14)	0.1158 (19)	0.0586 (12)	0.0245 (14)	−0.0046 (11)	−0.0347 (13)
O4M	0.0990 (14)	0.0434 (9)	0.0896 (11)	0.0043 (9)	0.0314 (10)	0.0095 (8)
C4M	0.111 (2)	0.0562 (13)	0.0779 (15)	0.0268 (14)	0.0129 (14)	0.0180 (11)

Geometric parameters (Å, º)

N1—N2	1.3348 (17)	C11A—C16A	1.396 (2)
N1—C11	1.398 (2)	C12A—C13A	1.385 (2)
N1—H1	0.826 (16)	C12A—H12A	0.9500
N2—C2	1.2957 (19)	C13A—C14A	1.369 (2)
C2—C21	1.462 (2)	C13A—H13A	0.9500
C2—C3	1.499 (2)	C14A—F14A	1.3719 (18)
C3—H3A	0.9800	C14A—C15A	1.376 (2)
C3—H3B	0.9800	C15A—C16A	1.380 (2)
C3—H3C	0.9800	C15A—H15A	0.9500
C11—C12	1.390 (2)	C16A—H16A	0.9500
C11—C16	1.394 (2)	C21A—N22A	1.3548 (18)
C12—C13	1.392 (2)	C21A—C26A	1.396 (2)
C12—H12	0.9500	N22A—C23A	1.344 (2)
C13—C14	1.366 (2)	N22A—H22A	0.883 (18)
C13—H13	0.9500	C23A—C24A	1.371 (2)
C14—C15	1.372 (2)	C23A—H23A	0.9500
C14—F14	1.3749 (18)	C24A—C25A	1.384 (2)
C15—C16	1.386 (2)	C24A—H24A	0.9500
C15—H15	0.9500	C25A—C26A	1.378 (2)
C16—H16	0.9500	C25A—H25A	0.9500
C21—N22	1.3521 (18)	C26A—H26A	0.9500
C21—C26	1.396 (2)	O1M—C1M	1.376 (2)
N22—C23	1.347 (2)	O1M—H1M	0.92 (3)
N22—H22	0.907 (17)	C1M—H1M1	0.9800
C23—C24	1.370 (2)	C1M—H1M2	0.9800
C23—H23	0.9500	C1M—H1M3	0.9800
C24—C25	1.382 (2)	O2M—C2M	1.405 (3)
C24—H24	0.9500	O2M—H2M	0.91 (3)
C25—C26	1.374 (2)	C2M—H2M1	0.9800
C25—H25	0.9500	C2M—H2M2	0.9800
C26—H26	0.9500	C2M—H2M3	0.9800
N1A—N2A	1.3360 (18)	O3M—C3M	1.399 (2)
N1A—C11A	1.404 (2)	O3M—H3M	0.86 (2)
N1A—H1A	0.834 (16)	C3M—H3MB	0.9800
N2A—C2A	1.296 (2)	C3M—H3MC	0.9800
C2A—C21A	1.460 (2)	C3M—H3MD	0.9800
C2A—C3A	1.502 (2)	O4M—C4M	1.408 (3)
C3A—H3A1	0.9800	O4M—H4M	0.85 (3)
C3A—H3A2	0.9800	C4M—H4M1	0.9800
C3A—H3A3	0.9800	C4M—H4M2	0.9800
C11A—C12A	1.391 (2)	C4M—H4M3	0.9800
N2—N1—C11	120.48 (12)	C12A—C11A—N1A	122.20 (15)
N2—N1—H1	119.0 (12)	C16A—C11A—N1A	117.72 (13)
C11—N1—H1	120.5 (12)	C13A—C12A—C11A	119.73 (15)
C2—N2—N1	118.58 (12)	C13A—C12A—H12A	120.1
N2—C2—C21	114.35 (13)	C11A—C12A—H12A	120.1
N2—C2—C3	124.89 (14)	C14A—C13A—C12A	118.86 (14)
C21—C2—C3	120.75 (14)	C14A—C13A—H13A	120.6
C2—C3—H3A	109.5	C12A—C13A—H13A	120.6
C2—C3—H3B	109.5	C13A—C14A—F14A	119.12 (14)
H3A—C3—H3B	109.5	C13A—C14A—C15A	122.80 (15)
C2—C3—H3C	109.5	F14A—C14A—C15A	118.09 (15)
H3A—C3—H3C	109.5	C14A—C15A—C16A	118.51 (15)
H3B—C3—H3C	109.5	C14A—C15A—H15A	120.7
C12—C11—C16	119.93 (15)	C16A—C15A—H15A	120.7
C12—C11—N1	122.36 (14)	C15A—C16A—C11A	120.03 (14)
C16—C11—N1	117.71 (13)	C15A—C16A—H16A	120.0
C11—C12—C13	119.80 (15)	C11A—C16A—H16A	120.0
C11—C12—H12	120.1	N22A—C21A—C26A	116.73 (14)
C13—C12—H12	120.1	N22A—C21A—C2A	118.07 (14)
C14—C13—C12	118.67 (14)	C26A—C21A—C2A	125.19 (14)
C14—C13—H13	120.7	C23A—N22A—C21A	123.85 (14)
C12—C13—H13	120.7	C23A—N22A—H22A	115.9 (11)
C13—C14—C15	123.09 (15)	C21A—N22A—H22A	120.2 (11)
C13—C14—F14	118.76 (13)	N22A—C23A—C24A	120.02 (15)
C15—C14—F14	118.15 (14)	N22A—C23A—H23A	120.0
C14—C15—C16	118.34 (15)	C24A—C23A—H23A	120.0
C14—C15—H15	120.8	C23A—C24A—C25A	118.54 (16)
C16—C15—H15	120.8	C23A—C24A—H24A	120.7
C15—C16—C11	120.17 (14)	C25A—C24A—H24A	120.7
C15—C16—H16	119.9	C26A—C25A—C24A	120.30 (16)
C11—C16—H16	119.9	C26A—C25A—H25A	119.8
N22—C21—C26	116.93 (14)	C24A—C25A—H25A	119.8
N22—C21—C2	118.06 (14)	C25A—C26A—C21A	120.55 (15)
C26—C21—C2	125.01 (13)	C25A—C26A—H26A	119.7
C23—N22—C21	123.83 (15)	C21A—C26A—H26A	119.7
C23—N22—H22	116.9 (10)	C1M—O1M—H1M	109.0 (15)
C21—N22—H22	119.1 (10)	O1M—C1M—H1M1	109.5
N22—C23—C24	119.74 (15)	O1M—C1M—H1M2	109.5
N22—C23—H23	120.1	H1M1—C1M—H1M2	109.5
C24—C23—H23	120.1	O1M—C1M—H1M3	109.5
C23—C24—C25	118.71 (15)	H1M1—C1M—H1M3	109.5
C23—C24—H24	120.6	H1M2—C1M—H1M3	109.5
C25—C24—H24	120.6	C2M—O2M—H2M	105.1 (19)
C26—C25—C24	120.45 (16)	O2M—C2M—H2M1	109.5
C26—C25—H25	119.8	O2M—C2M—H2M2	109.5
C24—C25—H25	119.8	H2M1—C2M—H2M2	109.5
C25—C26—C21	120.34 (14)	O2M—C2M—H2M3	109.5
C25—C26—H26	119.8	H2M1—C2M—H2M3	109.5
C21—C26—H26	119.8	H2M2—C2M—H2M3	109.5
N2A—N1A—C11A	119.75 (13)	C3M—O3M—H3M	113.1 (14)
N2A—N1A—H1A	121.1 (12)	O3M—C3M—H3MB	109.5
C11A—N1A—H1A	118.8 (12)	O3M—C3M—H3MC	109.5
C2A—N2A—N1A	118.60 (13)	H3MB—C3M—H3MC	109.5
N2A—C2A—C21A	114.45 (13)	O3M—C3M—H3MD	109.5
N2A—C2A—C3A	124.25 (14)	H3MB—C3M—H3MD	109.5
C21A—C2A—C3A	121.30 (14)	H3MC—C3M—H3MD	109.5
C2A—C3A—H3A1	109.5	C4M—O4M—H4M	113.1 (18)
C2A—C3A—H3A2	109.5	O4M—C4M—H4M1	109.5
H3A1—C3A—H3A2	109.5	O4M—C4M—H4M2	109.5
C2A—C3A—H3A3	109.5	H4M1—C4M—H4M2	109.5
H3A1—C3A—H3A3	109.5	O4M—C4M—H4M3	109.5
H3A2—C3A—H3A3	109.5	H4M1—C4M—H4M3	109.5
C12A—C11A—C16A	120.06 (14)	H4M2—C4M—H4M3	109.5
C11—N1—N2—C2	−177.23 (15)	C11A—N1A—N2A—C2A	−178.80 (14)
N1—N2—C2—C21	−179.79 (13)	N1A—N2A—C2A—C21A	178.98 (13)
N1—N2—C2—C3	1.0 (2)	N1A—N2A—C2A—C3A	−1.0 (2)
N2—N1—C11—C12	−2.0 (2)	N2A—N1A—C11A—C12A	−4.7 (2)
N2—N1—C11—C16	177.91 (14)	N2A—N1A—C11A—C16A	176.85 (13)
C16—C11—C12—C13	0.1 (2)	C16A—C11A—C12A—C13A	0.2 (2)
N1—C11—C12—C13	−179.99 (15)	N1A—C11A—C12A—C13A	−178.22 (14)
C11—C12—C13—C14	−0.3 (2)	C11A—C12A—C13A—C14A	−0.1 (2)
C12—C13—C14—C15	0.4 (3)	C12A—C13A—C14A—F14A	−179.98 (14)
C12—C13—C14—F14	−179.52 (14)	C12A—C13A—C14A—C15A	−0.2 (2)
C13—C14—C15—C16	−0.3 (2)	C13A—C14A—C15A—C16A	0.4 (2)
F14—C14—C15—C16	179.62 (14)	F14A—C14A—C15A—C16A	−179.82 (14)
C14—C15—C16—C11	0.1 (2)	C14A—C15A—C16A—C11A	−0.3 (2)
C12—C11—C16—C15	0.0 (2)	C12A—C11A—C16A—C15A	0.0 (2)
N1—C11—C16—C15	−179.91 (15)	N1A—C11A—C16A—C15A	178.49 (14)
N2—C2—C21—N22	−4.6 (2)	N2A—C2A—C21A—N22A	3.5 (2)
C3—C2—C21—N22	174.62 (14)	C3A—C2A—C21A—N22A	−176.59 (13)
N2—C2—C21—C26	175.62 (15)	N2A—C2A—C21A—C26A	−175.71 (15)
C3—C2—C21—C26	−5.2 (2)	C3A—C2A—C21A—C26A	4.2 (2)
C26—C21—N22—C23	−0.3 (2)	C26A—C21A—N22A—C23A	−0.5 (2)
C2—C21—N22—C23	179.86 (15)	C2A—C21A—N22A—C23A	−179.70 (14)
C21—N22—C23—C24	0.4 (2)	C21A—N22A—C23A—C24A	0.6 (2)
N22—C23—C24—C25	−0.4 (3)	N22A—C23A—C24A—C25A	−0.2 (2)
C23—C24—C25—C26	0.4 (3)	C23A—C24A—C25A—C26A	−0.2 (3)
C24—C25—C26—C21	−0.3 (3)	C24A—C25A—C26A—C21A	0.2 (3)
N22—C21—C26—C25	0.3 (2)	N22A—C21A—C26A—C25A	0.1 (2)
C2—C21—C26—C25	−179.95 (16)	C2A—C21A—C26A—C25A	179.24 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1M	0.826 (16)	2.158 (16)	2.9136 (17)	152.1 (14)
N22—H22···Cl1^i	0.907 (17)	2.401 (16)	3.1633 (15)	141.8 (13)
N1A—H1A···O3M	0.834 (16)	2.081 (17)	2.8806 (18)	160.4 (16)
N22A—H22A···Cl2^ii	0.883 (18)	2.382 (18)	3.1292 (15)	142.5 (15)
O1M—H1M···Cl1	0.92 (3)	2.18 (3)	3.0807 (16)	168 (2)
O2M—H2M···Cl1	0.91 (3)	2.19 (3)	3.1029 (17)	178 (3)
O3M—H3M···Cl2	0.86 (2)	2.21 (2)	3.0678 (16)	172 (2)
O4M—H4M···Cl2	0.85 (3)	2.30 (3)	3.1329 (18)	167 (2)
C25—H25···O2M^iii	0.95	2.42	3.315 (2)	157
C25A—H25A···O4M^iv	0.95	2.44	3.318 (3)	153

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