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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 (\overline{2}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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110019827/dn3144sup1.cif
Contains datablocks I, II, III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110019827/dn3144Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110019827/dn3144IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110019827/dn3144IIIsup4.hkl
Contains datablock III

CCDC references: 786820; 786821; 786822

Computing details top

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 top
Crystal data top
C13H13ClN3+·Cl·CH4OF(000) = 656
Mr = 314.21Dx = 1.404 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 27165 reflections
a = 7.6715 (5) Åθ = 2.5–29.8°
b = 16.0963 (10) ŵ = 0.44 mm1
c = 12.0406 (8) ÅT = 173 K
β = 91.666 (5)°Plate, yellow
V = 1486.18 (17) Å30.38 × 0.24 × 0.08 mm
Z = 4
Data collection top
Stoe IPDS II two-circle
diffractometer
4284 independent reflections
Radiation source: fine-focus sealed tube3625 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
ω scansθmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan
(MULABS; Spek, 2009; Blessing, 1995)
h = 1010
Tmin = 0.852, Tmax = 0.966k = 2221
24993 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0542P)2 + 0.234P]
where P = (Fo2 + 2Fc2)/3
4284 reflections(Δ/σ)max < 0.001
195 parametersΔρmax = 0.44 e Å3
0 restraintsΔρmin = 0.23 e Å3
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 > 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 (Å2) top
xyzUiso*/Ueq
O1M0.54425 (15)0.47942 (6)0.19018 (10)0.0415 (2)
H1M0.445 (3)0.4919 (14)0.1819 (18)0.055 (6)*
C1M0.6524 (2)0.53177 (10)0.12768 (14)0.0463 (3)
H1A0.60350.58800.12580.069*
H1B0.65890.51030.05170.069*
H1C0.76960.53320.16220.069*
Cl10.15567 (4)0.54088 (2)0.17191 (3)0.03914 (9)
N10.64542 (14)0.31183 (7)0.23998 (9)0.0303 (2)
H10.629 (3)0.3635 (14)0.2337 (16)0.052 (5)*
N20.73493 (13)0.27757 (6)0.32529 (8)0.02792 (19)
C20.81091 (15)0.32529 (8)0.39868 (10)0.0286 (2)
C30.80979 (18)0.41842 (8)0.39609 (12)0.0376 (3)
H3A0.87770.43790.33350.056*
H3B0.86150.43990.46570.056*
H3C0.68940.43830.38730.056*
C110.55996 (14)0.25978 (7)0.16277 (10)0.0278 (2)
C120.55353 (16)0.17419 (8)0.17739 (11)0.0324 (2)
H120.60560.14970.24200.039*
C130.47108 (17)0.12448 (8)0.09766 (11)0.0334 (2)
H130.46630.06600.10770.040*
C140.39583 (15)0.16047 (8)0.00342 (10)0.0301 (2)
Cl140.29572 (4)0.09690 (2)0.09736 (3)0.03741 (9)
C150.40172 (17)0.24567 (8)0.01256 (10)0.0328 (2)
H150.35020.26980.07760.039*
C160.48341 (17)0.29545 (8)0.06717 (10)0.0322 (2)
H160.48750.35390.05690.039*
C210.90240 (15)0.27999 (7)0.48900 (10)0.0284 (2)
N220.91829 (13)0.19631 (7)0.47922 (9)0.0294 (2)
H220.875 (3)0.1726 (12)0.4175 (16)0.048 (5)*
C230.99749 (17)0.14786 (9)0.55637 (11)0.0345 (3)
H231.00480.08960.54500.041*
C241.06794 (18)0.18271 (10)0.65181 (11)0.0391 (3)
H241.12550.14920.70650.047*
C251.05303 (18)0.26772 (10)0.66626 (11)0.0395 (3)
H251.09950.29280.73210.047*
C260.97090 (16)0.31677 (9)0.58562 (10)0.0343 (2)
H260.96140.37510.59620.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1M0.0404 (5)0.0293 (5)0.0548 (6)0.0057 (4)0.0013 (4)0.0104 (4)
C1M0.0538 (8)0.0401 (8)0.0450 (7)0.0014 (6)0.0044 (6)0.0089 (6)
Cl10.03931 (16)0.02899 (15)0.04833 (18)0.00277 (11)0.01206 (13)0.00109 (12)
N10.0324 (5)0.0232 (5)0.0351 (5)0.0033 (4)0.0057 (4)0.0034 (4)
N20.0268 (4)0.0262 (5)0.0307 (4)0.0029 (3)0.0015 (4)0.0031 (4)
C20.0269 (5)0.0255 (5)0.0334 (5)0.0023 (4)0.0000 (4)0.0003 (4)
C30.0390 (6)0.0250 (6)0.0483 (7)0.0026 (5)0.0071 (5)0.0001 (5)
C110.0252 (5)0.0268 (5)0.0313 (5)0.0031 (4)0.0004 (4)0.0027 (4)
C120.0335 (6)0.0287 (6)0.0344 (5)0.0010 (4)0.0069 (4)0.0072 (4)
C130.0354 (6)0.0264 (5)0.0378 (6)0.0009 (4)0.0060 (5)0.0056 (4)
C140.0284 (5)0.0313 (6)0.0304 (5)0.0006 (4)0.0009 (4)0.0015 (4)
Cl140.04054 (17)0.03700 (17)0.03424 (15)0.00031 (12)0.00668 (11)0.00151 (11)
C150.0356 (6)0.0325 (6)0.0300 (5)0.0038 (5)0.0033 (4)0.0055 (4)
C160.0357 (6)0.0256 (5)0.0351 (6)0.0039 (4)0.0029 (5)0.0056 (4)
C210.0264 (5)0.0277 (5)0.0311 (5)0.0005 (4)0.0016 (4)0.0004 (4)
N220.0295 (5)0.0280 (5)0.0307 (5)0.0017 (4)0.0023 (4)0.0023 (4)
C230.0327 (6)0.0344 (6)0.0362 (6)0.0029 (5)0.0009 (5)0.0090 (5)
C240.0348 (6)0.0497 (8)0.0326 (6)0.0017 (5)0.0021 (5)0.0100 (5)
C250.0371 (6)0.0525 (8)0.0288 (5)0.0054 (6)0.0020 (5)0.0008 (5)
C260.0331 (6)0.0364 (6)0.0335 (6)0.0022 (5)0.0000 (5)0.0031 (5)
Geometric parameters (Å, º) top
O1M—C1M1.4145 (19)C13—C141.3850 (16)
O1M—H1M0.79 (2)C13—H130.9500
C1M—H1A0.9800C14—C151.3859 (17)
C1M—H1B0.9800C14—Cl141.7478 (13)
C1M—H1C0.9800C15—C161.3862 (18)
N1—N21.3378 (13)C15—H150.9500
N1—C111.4002 (16)C16—H160.9500
N1—H10.84 (2)C21—N221.3579 (15)
N2—C21.2964 (15)C21—C261.3945 (17)
C2—C211.4706 (16)N22—C231.3445 (15)
C2—C31.4994 (18)N22—H220.89 (2)
C3—H3A0.9800C23—C241.3752 (19)
C3—H3B0.9800C23—H230.9500
C3—H3C0.9800C24—C251.385 (2)
C11—C121.3900 (17)C24—H240.9500
C11—C161.4000 (16)C25—C261.3883 (19)
C12—C131.3881 (18)C25—H250.9500
C12—H120.9500C26—H260.9500
C1M—O1M—H1M111.1 (16)C12—C13—H13120.1
O1M—C1M—H1A109.5C13—C14—C15120.87 (12)
O1M—C1M—H1B109.5C13—C14—Cl14119.22 (10)
H1A—C1M—H1B109.5C15—C14—Cl14119.89 (9)
O1M—C1M—H1C109.5C14—C15—C16119.46 (11)
H1A—C1M—H1C109.5C14—C15—H15120.3
H1B—C1M—H1C109.5C16—C15—H15120.3
N2—N1—C11118.89 (10)C15—C16—C11120.18 (11)
N2—N1—H1123.1 (14)C15—C16—H16119.9
C11—N1—H1117.7 (14)C11—C16—H16119.9
C2—N2—N1119.32 (10)N22—C21—C26117.44 (11)
N2—C2—C21113.94 (10)N22—C21—C2118.02 (11)
N2—C2—C3125.17 (11)C26—C21—C2124.52 (11)
C21—C2—C3120.89 (11)C23—N22—C21123.74 (11)
C2—C3—H3A109.5C23—N22—H22118.6 (13)
C2—C3—H3B109.5C21—N22—H22117.7 (13)
H3A—C3—H3B109.5N22—C23—C24119.96 (13)
C2—C3—H3C109.5N22—C23—H23120.0
H3A—C3—H3C109.5C24—C23—H23120.0
H3B—C3—H3C109.5C23—C24—C25118.44 (12)
C12—C11—C16119.67 (11)C23—C24—H24120.8
C12—C11—N1121.77 (11)C25—C24—H24120.8
C16—C11—N1118.53 (11)C24—C25—C26120.77 (12)
C13—C12—C11120.06 (11)C24—C25—H25119.6
C13—C12—H12120.0C26—C25—H25119.6
C11—C12—H12120.0C25—C26—C21119.63 (13)
C14—C13—C12119.75 (11)C25—C26—H26120.2
C14—C13—H13120.1C21—C26—H26120.2
C11—N1—N2—C2178.32 (10)N1—C11—C16—C15178.28 (11)
N1—N2—C2—C21179.07 (10)N2—C2—C21—N228.60 (15)
N1—N2—C2—C30.84 (18)C3—C2—C21—N22171.49 (11)
N2—N1—C11—C125.45 (17)N2—C2—C21—C26169.87 (11)
N2—N1—C11—C16172.83 (10)C3—C2—C21—C2610.05 (18)
C16—C11—C12—C130.20 (18)C26—C21—N22—C230.81 (17)
N1—C11—C12—C13178.47 (11)C2—C21—N22—C23179.38 (11)
C11—C12—C13—C140.20 (19)C21—N22—C23—C240.05 (19)
C12—C13—C14—C150.04 (19)N22—C23—C24—C250.77 (19)
C12—C13—C14—Cl14178.92 (10)C23—C24—C25—C260.8 (2)
C13—C14—C15—C160.28 (19)C24—C25—C26—C210.08 (19)
Cl14—C14—C15—C16179.15 (10)N22—C21—C26—C250.72 (17)
C14—C15—C16—C110.28 (19)C2—C21—C26—C25179.19 (11)
C12—C11—C16—C150.04 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1M0.84 (2)2.04 (2)2.8656 (14)165.9 (19)
O1M—H1M···Cl10.79 (2)2.35 (2)3.1425 (12)174 (2)
N22—H22···Cl1i0.89 (2)2.39 (2)3.1356 (11)141.8 (17)
Symmetry code: (i) x+1, y1/2, z+1/2.
(II) 2-{1-[(4-fluoroanilino)methylidene]ethyl}pyridinium chloride top
Crystal data top
C13H13FN3+·ClF(000) = 552
Mr = 265.71Dx = 1.411 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6800 reflections
a = 6.8522 (12) Åθ = 3.5–25.1°
b = 11.5134 (16) ŵ = 0.30 mm1
c = 15.856 (2) ÅT = 173 K
β = 90.048 (16)°Plate, yellow
V = 1250.9 (3) Å30.38 × 0.09 × 0.05 mm
Z = 4
Data collection top
Stoe IPDS II two-circle
diffractometer
2161 independent reflections
Radiation source: fine-focus sealed tube1662 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.116
ω scansθmax = 25.2°, θmin = 3.5°
Absorption correction: multi-scan
(MULABS; Spek, 2009; Blessing, 1995)
h = 88
Tmin = 0.894, Tmax = 0.985k = 1313
6993 measured reflectionsl = 1618
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.1013P)2]
where P = (Fo2 + 2Fc2)/3
2161 reflections(Δ/σ)max < 0.001
165 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.63 e Å3
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 > 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 (Å2) top
xyzUiso*/Ueq
Cl10.2216 (2)0.34607 (8)0.83240 (8)0.0438 (3)
N10.3060 (5)0.6598 (3)0.5108 (2)0.0278 (7)
H10.33110.69430.55910.033*
N20.2655 (5)0.5455 (2)0.5080 (2)0.0274 (7)
C20.2679 (6)0.4873 (3)0.5780 (3)0.0274 (9)
C30.3159 (8)0.5389 (4)0.6620 (3)0.0418 (11)
H3A0.41970.59670.65540.063*
H3B0.36010.47740.70030.063*
H3C0.19950.57630.68540.063*
C110.3073 (6)0.7226 (3)0.4350 (3)0.0272 (8)
C120.2687 (7)0.6694 (3)0.3575 (3)0.0336 (9)
H120.24020.58870.35540.040*
C130.2719 (7)0.7337 (4)0.2843 (3)0.0392 (10)
H130.24120.69880.23170.047*
C140.3204 (6)0.8498 (4)0.2891 (3)0.0377 (10)
F140.3282 (5)0.9128 (2)0.2154 (2)0.0545 (8)
C150.3614 (6)0.9051 (4)0.3636 (3)0.0352 (10)
H150.39370.98540.36450.042*
C160.3545 (6)0.8412 (3)0.4377 (3)0.0313 (9)
H160.38170.87760.49020.038*
C210.2221 (6)0.3637 (3)0.5681 (3)0.0253 (8)
N220.2141 (5)0.2941 (3)0.6362 (2)0.0315 (8)
H220.23380.32510.68620.038*
C230.1774 (6)0.1792 (4)0.6315 (3)0.0351 (10)
H230.17540.13410.68170.042*
C240.1433 (6)0.1270 (4)0.5558 (3)0.0373 (11)
H240.11730.04610.55280.045*
C250.1473 (6)0.1948 (4)0.4827 (3)0.0355 (10)
H250.12410.16040.42920.043*
C260.1853 (6)0.3123 (3)0.4890 (3)0.0280 (8)
H260.18660.35900.43960.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0652 (7)0.0299 (5)0.0362 (6)0.0003 (5)0.0012 (6)0.0052 (5)
N10.0352 (17)0.0241 (14)0.0242 (17)0.0020 (14)0.0029 (14)0.0029 (13)
N20.0269 (16)0.0239 (15)0.0315 (19)0.0010 (13)0.0018 (14)0.0005 (13)
C20.0264 (18)0.0256 (18)0.030 (2)0.0009 (15)0.0052 (17)0.0006 (16)
C30.064 (3)0.031 (2)0.030 (2)0.004 (2)0.004 (3)0.0029 (19)
C110.0228 (17)0.0270 (18)0.032 (2)0.0022 (15)0.0053 (16)0.0022 (16)
C120.039 (2)0.0283 (19)0.034 (2)0.0013 (18)0.0006 (18)0.0027 (16)
C130.042 (2)0.038 (2)0.037 (3)0.003 (2)0.002 (2)0.0027 (19)
C140.037 (2)0.042 (2)0.034 (3)0.0005 (19)0.002 (2)0.017 (2)
F140.0655 (18)0.0563 (17)0.0417 (17)0.0007 (15)0.0009 (15)0.0267 (14)
C150.036 (2)0.029 (2)0.041 (3)0.0019 (17)0.0041 (19)0.0107 (18)
C160.0302 (19)0.029 (2)0.035 (3)0.0009 (16)0.0014 (17)0.0027 (18)
C210.0218 (16)0.0274 (18)0.027 (2)0.0021 (15)0.0042 (15)0.0018 (15)
N220.0314 (16)0.0347 (17)0.0283 (18)0.0011 (15)0.0033 (15)0.0041 (14)
C230.031 (2)0.033 (2)0.042 (3)0.0023 (17)0.0004 (19)0.0135 (19)
C240.0313 (19)0.0261 (19)0.054 (3)0.0031 (16)0.002 (2)0.009 (2)
C250.037 (2)0.029 (2)0.040 (3)0.0031 (17)0.003 (2)0.0046 (19)
C260.0319 (19)0.0290 (18)0.023 (2)0.0005 (15)0.0011 (16)0.0022 (16)
Geometric parameters (Å, º) top
N1—N21.345 (4)C14—F141.376 (5)
N1—C111.402 (5)C15—C161.387 (6)
N1—H10.8800C15—H150.9500
N2—C21.297 (5)C16—H160.9500
C2—C211.465 (5)C21—N221.345 (5)
C2—C31.495 (6)C21—C261.410 (6)
C3—H3A0.9800N22—C231.349 (5)
C3—H3B0.9800N22—H220.8800
C3—H3C0.9800C23—C241.363 (7)
C11—C121.398 (6)C23—H230.9500
C11—C161.404 (6)C24—C251.398 (7)
C12—C131.377 (6)C24—H240.9500
C12—H120.9500C25—C261.381 (6)
C13—C141.379 (6)C25—H250.9500
C13—H130.9500C26—H260.9500
C14—C151.372 (7)
N2—N1—C11118.5 (3)C14—C15—C16118.5 (4)
N2—N1—H1120.8C14—C15—H15120.8
C11—N1—H1120.8C16—C15—H15120.8
C2—N2—N1118.3 (3)C15—C16—C11119.9 (4)
N2—C2—C21114.1 (3)C15—C16—H16120.1
N2—C2—C3124.0 (3)C11—C16—H16120.1
C21—C2—C3121.8 (4)N22—C21—C26117.2 (3)
C2—C3—H3A109.5N22—C21—C2120.1 (4)
C2—C3—H3B109.5C26—C21—C2122.7 (3)
H3A—C3—H3B109.5C21—N22—C23123.2 (4)
C2—C3—H3C109.5C21—N22—H22118.4
H3A—C3—H3C109.5C23—N22—H22118.4
H3B—C3—H3C109.5N22—C23—C24120.9 (4)
C12—C11—N1121.7 (3)N22—C23—H23119.6
C12—C11—C16119.7 (4)C24—C23—H23119.6
N1—C11—C16118.5 (4)C23—C24—C25118.7 (4)
C13—C12—C11120.2 (4)C23—C24—H24120.6
C13—C12—H12119.9C25—C24—H24120.6
C11—C12—H12119.9C26—C25—C24119.4 (4)
C12—C13—C14118.6 (4)C26—C25—H25120.3
C12—C13—H13120.7C24—C25—H25120.3
C14—C13—H13120.7C25—C26—C21120.6 (4)
C15—C14—F14118.6 (4)C25—C26—H26119.7
C15—C14—C13123.1 (4)C21—C26—H26119.7
F14—C14—C13118.3 (4)
C11—N1—N2—C2178.8 (4)N1—C11—C16—C15178.6 (4)
N1—N2—C2—C21179.9 (3)N2—C2—C21—N22178.1 (4)
N1—N2—C2—C31.0 (6)C3—C2—C21—N222.9 (6)
N2—N1—C11—C120.3 (6)N2—C2—C21—C262.0 (5)
N2—N1—C11—C16178.4 (3)C3—C2—C21—C26177.0 (4)
N1—C11—C12—C13179.8 (4)C26—C21—N22—C231.5 (6)
C16—C11—C12—C131.7 (7)C2—C21—N22—C23178.4 (4)
C11—C12—C13—C142.2 (7)C21—N22—C23—C240.9 (6)
C12—C13—C14—C151.6 (7)N22—C23—C24—C250.1 (6)
C12—C13—C14—F14178.3 (4)C23—C24—C25—C260.1 (6)
F14—C14—C15—C16179.6 (4)C24—C25—C26—C210.7 (6)
C13—C14—C15—C160.3 (7)N22—C21—C26—C251.4 (6)
C14—C15—C16—C110.3 (6)C2—C21—C26—C25178.4 (4)
C12—C11—C16—C150.4 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N22—H22···Cl10.882.333.168 (4)159
N1—H1···Cl1i0.882.483.289 (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 top
Crystal data top
C13H13FN3+·Cl·2CH4OZ = 4
Mr = 329.80F(000) = 696
Triclinic, P1Dx = 1.289 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0088 (8) ÅCell parameters from 12810 reflections
b = 11.7258 (14) Åθ = 2.2–27.2°
c = 21.843 (2) ŵ = 0.25 mm1
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) Å3
Data collection top
Stoe IPDS II two-circle
diffractometer
7158 independent reflections
Radiation source: fine-focus sealed tube4239 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 27.2°, θmin = 2.5°
Absorption correction: multi-scan
(MULABS; Spek, 2009; Blessing, 1995)
h = 89
Tmin = 0.904, Tmax = 0.967k = 1515
21250 measured reflectionsl = 2727
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058H atoms treated by a mixture of independent and constrained refinement
S = 0.85 w = 1/[σ2(Fo2) + (0.020P)2]
where P = (Fo2 + 2Fc2)/3
7158 reflections(Δ/σ)max = 0.001
435 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.14 e Å3
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 > 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 (Å2) top
xyzUiso*/Ueq
Cl10.06824 (7)0.39520 (4)0.835725 (17)0.04234 (11)
Cl20.70783 (7)0.36712 (4)0.328298 (17)0.04196 (11)
N10.7276 (2)0.48488 (11)0.94796 (6)0.0351 (3)
H10.683 (3)0.4436 (15)0.9145 (8)0.040 (5)*
N20.69117 (19)0.43426 (11)0.99985 (5)0.0315 (3)
C20.5986 (2)0.31994 (13)0.99561 (6)0.0326 (3)
C30.5307 (3)0.23792 (14)0.93617 (7)0.0449 (4)
H3A0.64180.24940.90920.067*
H3B0.41890.25660.91570.067*
H3C0.48700.15410.94480.067*
C110.8345 (2)0.60680 (13)0.95032 (7)0.0318 (3)
C120.9020 (2)0.68115 (13)1.00578 (7)0.0357 (4)
H120.87600.64961.04390.043*
C131.0078 (2)0.80191 (14)1.00527 (7)0.0385 (4)
H131.05420.85381.04280.046*
C141.0437 (2)0.84435 (13)0.94967 (7)0.0371 (4)
F141.14943 (15)0.96342 (8)0.94906 (4)0.0510 (3)
C150.9790 (2)0.77361 (13)0.89407 (7)0.0372 (4)
H151.00610.80630.85630.045*
C160.8734 (2)0.65336 (14)0.89447 (7)0.0358 (4)
H160.82730.60250.85660.043*
C210.5654 (2)0.27333 (13)1.05501 (6)0.0322 (3)
N220.6445 (2)0.34944 (12)1.10693 (6)0.0331 (3)
H220.722 (2)0.4254 (15)1.1036 (7)0.036 (4)*
C230.6243 (3)0.31773 (14)1.16431 (7)0.0389 (4)
H230.68250.37531.19920.047*
C240.5195 (3)0.20214 (15)1.17223 (7)0.0416 (4)
H240.50480.17841.21240.050*
C250.4355 (3)0.12077 (14)1.12061 (7)0.0421 (4)
H250.36170.04041.12530.051*
C260.4581 (2)0.15534 (14)1.06253 (7)0.0376 (4)
H260.40030.09871.02730.045*
N1A0.2446 (2)0.48192 (11)0.45536 (6)0.0343 (3)
H1A0.226 (2)0.4372 (14)0.4218 (8)0.038 (5)*
N2A0.18085 (19)0.43786 (11)0.50735 (5)0.0325 (3)
C2A0.0736 (2)0.32604 (13)0.50393 (7)0.0330 (3)
C3A0.0126 (3)0.24187 (14)0.44479 (7)0.0406 (4)
H3A10.05010.27880.41490.061*
H3A20.08310.16610.45290.061*
H3A30.13110.22580.42800.061*
C11A0.3642 (2)0.60216 (13)0.45792 (7)0.0319 (3)
C12A0.4080 (2)0.68097 (13)0.51257 (7)0.0348 (4)
H12A0.35970.65360.55010.042*
C13A0.5222 (3)0.79955 (14)0.51206 (7)0.0395 (4)
H13A0.55290.85430.54900.047*
C14A0.5899 (3)0.83650 (13)0.45735 (7)0.0396 (4)
F14A0.70313 (17)0.95385 (8)0.45658 (4)0.0582 (3)
C15A0.5499 (2)0.76067 (14)0.40260 (7)0.0381 (4)
H15A0.59980.78900.36540.046*
C16A0.4356 (2)0.64250 (13)0.40288 (7)0.0351 (4)
H16A0.40550.58860.36560.042*
C21A0.0143 (2)0.28592 (13)0.56329 (6)0.0322 (3)
N22A0.0658 (2)0.36833 (12)0.61436 (6)0.0333 (3)
H22A0.135 (3)0.4436 (16)0.6114 (8)0.043 (5)*
C23A0.0209 (2)0.34280 (14)0.67159 (7)0.0382 (4)
H23A0.06010.40470.70560.046*
C24A0.0813 (3)0.22747 (15)0.68089 (7)0.0434 (4)
H24A0.11340.20830.72120.052*
C25A0.1369 (3)0.13953 (15)0.63032 (7)0.0439 (4)
H25A0.20750.05900.63580.053*
C26A0.0901 (3)0.16818 (14)0.57208 (7)0.0387 (4)
H26A0.12930.10730.53760.046*
O1M0.5121 (2)0.40944 (12)0.82663 (5)0.0540 (3)
H1M0.377 (4)0.393 (2)0.8300 (11)0.089 (8)*
C1M0.5448 (4)0.3692 (3)0.76751 (9)0.0896 (8)
H1M10.46210.39440.73790.134*
H1M20.50900.28110.76230.134*
H1M30.68650.40320.76030.134*
O2M0.1240 (3)0.11921 (14)0.83089 (7)0.0780 (5)
H2M0.070 (4)0.200 (3)0.8328 (12)0.108 (9)*
C2M0.0255 (4)0.0708 (2)0.80911 (11)0.0791 (7)
H2M10.11950.12950.78730.119*
H2M20.03640.00300.78080.119*
H2M30.09760.05220.84410.119*
O3M0.2720 (2)0.36917 (12)0.33337 (5)0.0551 (3)
H3M0.396 (4)0.3716 (19)0.3358 (10)0.074 (7)*
C3M0.1617 (3)0.2922 (2)0.28236 (10)0.0819 (8)
H3MB0.02260.29360.28180.123*
H3MC0.16540.21000.28520.123*
H3MD0.22000.31890.24430.123*
O4M0.4818 (3)0.09243 (15)0.32573 (8)0.0804 (5)
H4M0.533 (4)0.168 (2)0.3318 (11)0.092 (8)*
C4M0.6154 (4)0.0320 (2)0.30259 (11)0.0806 (7)
H4M10.69220.07610.27140.121*
H4M20.53970.04950.28380.121*
H4M30.70740.02740.33650.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0473 (3)0.0388 (2)0.0346 (2)0.00589 (19)0.00038 (18)0.00106 (16)
Cl20.0474 (3)0.0388 (2)0.03419 (19)0.00654 (19)0.00114 (18)0.00019 (16)
N10.0409 (9)0.0336 (7)0.0264 (6)0.0058 (6)0.0008 (6)0.0003 (6)
N20.0313 (7)0.0336 (7)0.0297 (6)0.0101 (6)0.0027 (5)0.0031 (5)
C20.0317 (9)0.0340 (8)0.0303 (7)0.0083 (7)0.0021 (7)0.0014 (6)
C30.0565 (12)0.0363 (9)0.0345 (8)0.0058 (8)0.0011 (8)0.0032 (7)
C110.0307 (9)0.0327 (8)0.0319 (7)0.0105 (7)0.0005 (7)0.0011 (6)
C120.0394 (10)0.0366 (8)0.0316 (7)0.0127 (7)0.0022 (7)0.0030 (6)
C130.0392 (10)0.0371 (9)0.0367 (8)0.0110 (8)0.0031 (7)0.0031 (7)
C140.0341 (9)0.0295 (8)0.0458 (9)0.0077 (7)0.0002 (7)0.0033 (7)
F140.0584 (7)0.0320 (5)0.0549 (6)0.0028 (5)0.0002 (5)0.0040 (4)
C150.0397 (10)0.0374 (9)0.0354 (8)0.0117 (8)0.0038 (7)0.0074 (7)
C160.0372 (9)0.0377 (8)0.0311 (8)0.0110 (7)0.0001 (7)0.0004 (6)
C210.0290 (9)0.0336 (8)0.0325 (7)0.0093 (7)0.0001 (6)0.0009 (6)
N220.0352 (8)0.0302 (7)0.0319 (7)0.0071 (6)0.0024 (6)0.0034 (5)
C230.0443 (11)0.0412 (9)0.0305 (8)0.0130 (8)0.0009 (7)0.0021 (7)
C240.0480 (11)0.0427 (9)0.0352 (8)0.0135 (8)0.0049 (8)0.0087 (7)
C250.0429 (10)0.0347 (8)0.0469 (9)0.0074 (8)0.0062 (8)0.0084 (7)
C260.0366 (10)0.0339 (8)0.0383 (8)0.0064 (7)0.0018 (7)0.0005 (7)
N1A0.0408 (8)0.0328 (7)0.0259 (6)0.0070 (6)0.0032 (6)0.0009 (6)
N2A0.0344 (8)0.0350 (7)0.0280 (6)0.0101 (6)0.0025 (6)0.0054 (5)
C2A0.0313 (9)0.0354 (8)0.0309 (7)0.0090 (7)0.0007 (7)0.0027 (6)
C3A0.0455 (10)0.0397 (9)0.0310 (8)0.0063 (8)0.0011 (7)0.0002 (7)
C11A0.0310 (9)0.0336 (8)0.0308 (7)0.0098 (7)0.0010 (7)0.0042 (6)
C12A0.0356 (9)0.0393 (8)0.0287 (7)0.0113 (7)0.0009 (7)0.0018 (6)
C13A0.0431 (10)0.0381 (9)0.0337 (8)0.0096 (8)0.0016 (7)0.0022 (7)
C14A0.0406 (10)0.0306 (8)0.0418 (9)0.0031 (7)0.0009 (8)0.0034 (7)
F14A0.0738 (8)0.0352 (5)0.0507 (6)0.0054 (5)0.0041 (5)0.0027 (4)
C15A0.0420 (10)0.0398 (9)0.0314 (8)0.0089 (8)0.0051 (7)0.0085 (7)
C16A0.0382 (10)0.0364 (8)0.0291 (7)0.0106 (7)0.0004 (7)0.0007 (6)
C21A0.0296 (9)0.0354 (8)0.0304 (7)0.0093 (7)0.0016 (6)0.0018 (6)
N22A0.0347 (8)0.0329 (7)0.0287 (6)0.0054 (6)0.0010 (6)0.0027 (5)
C23A0.0396 (10)0.0437 (9)0.0283 (8)0.0086 (8)0.0008 (7)0.0032 (7)
C24A0.0474 (11)0.0477 (10)0.0319 (8)0.0085 (8)0.0008 (8)0.0093 (7)
C25A0.0474 (11)0.0383 (9)0.0419 (9)0.0053 (8)0.0007 (8)0.0101 (7)
C26A0.0411 (10)0.0342 (8)0.0364 (8)0.0059 (7)0.0006 (7)0.0022 (7)
O1M0.0491 (9)0.0727 (9)0.0365 (6)0.0180 (7)0.0033 (6)0.0053 (6)
C1M0.0633 (16)0.151 (2)0.0451 (11)0.0294 (16)0.0024 (11)0.0196 (14)
O2M0.1015 (14)0.0438 (9)0.0763 (10)0.0011 (9)0.0310 (9)0.0060 (7)
C2M0.119 (2)0.0541 (13)0.0682 (14)0.0286 (14)0.0057 (14)0.0166 (11)
O3M0.0476 (9)0.0655 (8)0.0425 (7)0.0097 (7)0.0049 (6)0.0136 (6)
C3M0.0587 (14)0.1158 (19)0.0586 (12)0.0245 (14)0.0046 (11)0.0347 (13)
O4M0.0990 (14)0.0434 (9)0.0896 (11)0.0043 (9)0.0314 (10)0.0095 (8)
C4M0.111 (2)0.0562 (13)0.0779 (15)0.0268 (14)0.0129 (14)0.0180 (11)
Geometric parameters (Å, º) top
N1—N21.3348 (17)C11A—C16A1.396 (2)
N1—C111.398 (2)C12A—C13A1.385 (2)
N1—H10.826 (16)C12A—H12A0.9500
N2—C21.2957 (19)C13A—C14A1.369 (2)
C2—C211.462 (2)C13A—H13A0.9500
C2—C31.499 (2)C14A—F14A1.3719 (18)
C3—H3A0.9800C14A—C15A1.376 (2)
C3—H3B0.9800C15A—C16A1.380 (2)
C3—H3C0.9800C15A—H15A0.9500
C11—C121.390 (2)C16A—H16A0.9500
C11—C161.394 (2)C21A—N22A1.3548 (18)
C12—C131.392 (2)C21A—C26A1.396 (2)
C12—H120.9500N22A—C23A1.344 (2)
C13—C141.366 (2)N22A—H22A0.883 (18)
C13—H130.9500C23A—C24A1.371 (2)
C14—C151.372 (2)C23A—H23A0.9500
C14—F141.3749 (18)C24A—C25A1.384 (2)
C15—C161.386 (2)C24A—H24A0.9500
C15—H150.9500C25A—C26A1.378 (2)
C16—H160.9500C25A—H25A0.9500
C21—N221.3521 (18)C26A—H26A0.9500
C21—C261.396 (2)O1M—C1M1.376 (2)
N22—C231.347 (2)O1M—H1M0.92 (3)
N22—H220.907 (17)C1M—H1M10.9800
C23—C241.370 (2)C1M—H1M20.9800
C23—H230.9500C1M—H1M30.9800
C24—C251.382 (2)O2M—C2M1.405 (3)
C24—H240.9500O2M—H2M0.91 (3)
C25—C261.374 (2)C2M—H2M10.9800
C25—H250.9500C2M—H2M20.9800
C26—H260.9500C2M—H2M30.9800
N1A—N2A1.3360 (18)O3M—C3M1.399 (2)
N1A—C11A1.404 (2)O3M—H3M0.86 (2)
N1A—H1A0.834 (16)C3M—H3MB0.9800
N2A—C2A1.296 (2)C3M—H3MC0.9800
C2A—C21A1.460 (2)C3M—H3MD0.9800
C2A—C3A1.502 (2)O4M—C4M1.408 (3)
C3A—H3A10.9800O4M—H4M0.85 (3)
C3A—H3A20.9800C4M—H4M10.9800
C3A—H3A30.9800C4M—H4M20.9800
C11A—C12A1.391 (2)C4M—H4M30.9800
N2—N1—C11120.48 (12)C12A—C11A—N1A122.20 (15)
N2—N1—H1119.0 (12)C16A—C11A—N1A117.72 (13)
C11—N1—H1120.5 (12)C13A—C12A—C11A119.73 (15)
C2—N2—N1118.58 (12)C13A—C12A—H12A120.1
N2—C2—C21114.35 (13)C11A—C12A—H12A120.1
N2—C2—C3124.89 (14)C14A—C13A—C12A118.86 (14)
C21—C2—C3120.75 (14)C14A—C13A—H13A120.6
C2—C3—H3A109.5C12A—C13A—H13A120.6
C2—C3—H3B109.5C13A—C14A—F14A119.12 (14)
H3A—C3—H3B109.5C13A—C14A—C15A122.80 (15)
C2—C3—H3C109.5F14A—C14A—C15A118.09 (15)
H3A—C3—H3C109.5C14A—C15A—C16A118.51 (15)
H3B—C3—H3C109.5C14A—C15A—H15A120.7
C12—C11—C16119.93 (15)C16A—C15A—H15A120.7
C12—C11—N1122.36 (14)C15A—C16A—C11A120.03 (14)
C16—C11—N1117.71 (13)C15A—C16A—H16A120.0
C11—C12—C13119.80 (15)C11A—C16A—H16A120.0
C11—C12—H12120.1N22A—C21A—C26A116.73 (14)
C13—C12—H12120.1N22A—C21A—C2A118.07 (14)
C14—C13—C12118.67 (14)C26A—C21A—C2A125.19 (14)
C14—C13—H13120.7C23A—N22A—C21A123.85 (14)
C12—C13—H13120.7C23A—N22A—H22A115.9 (11)
C13—C14—C15123.09 (15)C21A—N22A—H22A120.2 (11)
C13—C14—F14118.76 (13)N22A—C23A—C24A120.02 (15)
C15—C14—F14118.15 (14)N22A—C23A—H23A120.0
C14—C15—C16118.34 (15)C24A—C23A—H23A120.0
C14—C15—H15120.8C23A—C24A—C25A118.54 (16)
C16—C15—H15120.8C23A—C24A—H24A120.7
C15—C16—C11120.17 (14)C25A—C24A—H24A120.7
C15—C16—H16119.9C26A—C25A—C24A120.30 (16)
C11—C16—H16119.9C26A—C25A—H25A119.8
N22—C21—C26116.93 (14)C24A—C25A—H25A119.8
N22—C21—C2118.06 (14)C25A—C26A—C21A120.55 (15)
C26—C21—C2125.01 (13)C25A—C26A—H26A119.7
C23—N22—C21123.83 (15)C21A—C26A—H26A119.7
C23—N22—H22116.9 (10)C1M—O1M—H1M109.0 (15)
C21—N22—H22119.1 (10)O1M—C1M—H1M1109.5
N22—C23—C24119.74 (15)O1M—C1M—H1M2109.5
N22—C23—H23120.1H1M1—C1M—H1M2109.5
C24—C23—H23120.1O1M—C1M—H1M3109.5
C23—C24—C25118.71 (15)H1M1—C1M—H1M3109.5
C23—C24—H24120.6H1M2—C1M—H1M3109.5
C25—C24—H24120.6C2M—O2M—H2M105.1 (19)
C26—C25—C24120.45 (16)O2M—C2M—H2M1109.5
C26—C25—H25119.8O2M—C2M—H2M2109.5
C24—C25—H25119.8H2M1—C2M—H2M2109.5
C25—C26—C21120.34 (14)O2M—C2M—H2M3109.5
C25—C26—H26119.8H2M1—C2M—H2M3109.5
C21—C26—H26119.8H2M2—C2M—H2M3109.5
N2A—N1A—C11A119.75 (13)C3M—O3M—H3M113.1 (14)
N2A—N1A—H1A121.1 (12)O3M—C3M—H3MB109.5
C11A—N1A—H1A118.8 (12)O3M—C3M—H3MC109.5
C2A—N2A—N1A118.60 (13)H3MB—C3M—H3MC109.5
N2A—C2A—C21A114.45 (13)O3M—C3M—H3MD109.5
N2A—C2A—C3A124.25 (14)H3MB—C3M—H3MD109.5
C21A—C2A—C3A121.30 (14)H3MC—C3M—H3MD109.5
C2A—C3A—H3A1109.5C4M—O4M—H4M113.1 (18)
C2A—C3A—H3A2109.5O4M—C4M—H4M1109.5
H3A1—C3A—H3A2109.5O4M—C4M—H4M2109.5
C2A—C3A—H3A3109.5H4M1—C4M—H4M2109.5
H3A1—C3A—H3A3109.5O4M—C4M—H4M3109.5
H3A2—C3A—H3A3109.5H4M1—C4M—H4M3109.5
C12A—C11A—C16A120.06 (14)H4M2—C4M—H4M3109.5
C11—N1—N2—C2177.23 (15)C11A—N1A—N2A—C2A178.80 (14)
N1—N2—C2—C21179.79 (13)N1A—N2A—C2A—C21A178.98 (13)
N1—N2—C2—C31.0 (2)N1A—N2A—C2A—C3A1.0 (2)
N2—N1—C11—C122.0 (2)N2A—N1A—C11A—C12A4.7 (2)
N2—N1—C11—C16177.91 (14)N2A—N1A—C11A—C16A176.85 (13)
C16—C11—C12—C130.1 (2)C16A—C11A—C12A—C13A0.2 (2)
N1—C11—C12—C13179.99 (15)N1A—C11A—C12A—C13A178.22 (14)
C11—C12—C13—C140.3 (2)C11A—C12A—C13A—C14A0.1 (2)
C12—C13—C14—C150.4 (3)C12A—C13A—C14A—F14A179.98 (14)
C12—C13—C14—F14179.52 (14)C12A—C13A—C14A—C15A0.2 (2)
C13—C14—C15—C160.3 (2)C13A—C14A—C15A—C16A0.4 (2)
F14—C14—C15—C16179.62 (14)F14A—C14A—C15A—C16A179.82 (14)
C14—C15—C16—C110.1 (2)C14A—C15A—C16A—C11A0.3 (2)
C12—C11—C16—C150.0 (2)C12A—C11A—C16A—C15A0.0 (2)
N1—C11—C16—C15179.91 (15)N1A—C11A—C16A—C15A178.49 (14)
N2—C2—C21—N224.6 (2)N2A—C2A—C21A—N22A3.5 (2)
C3—C2—C21—N22174.62 (14)C3A—C2A—C21A—N22A176.59 (13)
N2—C2—C21—C26175.62 (15)N2A—C2A—C21A—C26A175.71 (15)
C3—C2—C21—C265.2 (2)C3A—C2A—C21A—C26A4.2 (2)
C26—C21—N22—C230.3 (2)C26A—C21A—N22A—C23A0.5 (2)
C2—C21—N22—C23179.86 (15)C2A—C21A—N22A—C23A179.70 (14)
C21—N22—C23—C240.4 (2)C21A—N22A—C23A—C24A0.6 (2)
N22—C23—C24—C250.4 (3)N22A—C23A—C24A—C25A0.2 (2)
C23—C24—C25—C260.4 (3)C23A—C24A—C25A—C26A0.2 (3)
C24—C25—C26—C210.3 (3)C24A—C25A—C26A—C21A0.2 (3)
N22—C21—C26—C250.3 (2)N22A—C21A—C26A—C25A0.1 (2)
C2—C21—C26—C25179.95 (16)C2A—C21A—C26A—C25A179.24 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1M0.826 (16)2.158 (16)2.9136 (17)152.1 (14)
N22—H22···Cl1i0.907 (17)2.401 (16)3.1633 (15)141.8 (13)
N1A—H1A···O3M0.834 (16)2.081 (17)2.8806 (18)160.4 (16)
N22A—H22A···Cl2ii0.883 (18)2.382 (18)3.1292 (15)142.5 (15)
O1M—H1M···Cl10.92 (3)2.18 (3)3.0807 (16)168 (2)
O2M—H2M···Cl10.91 (3)2.19 (3)3.1029 (17)178 (3)
O3M—H3M···Cl20.86 (2)2.21 (2)3.0678 (16)172 (2)
O4M—H4M···Cl20.85 (3)2.30 (3)3.1329 (18)167 (2)
C25—H25···O2Miii0.952.423.315 (2)157
C25A—H25A···O4Miv0.952.443.318 (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.
 

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