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Specific short contacts are important in crystal engineering. Hydrogen bonds have been particularly successful and together with halogen bonds can be useful for assembling small molecules or ions into crystals. The ionic constituents in the isomorphous 3,5-di­chloro­pyridinium (3,5-diClPy) tetra­halometallates 3,5-di­chloro­pyridinium tetra­chlorido­zincate(II), (C5H4Cl2N)2[ZnCl4] or (3,5-diClPy)2ZnCl4, 3,5-di­chloro­pyridinium tetra­bromido­zincate(II), (C5H4Cl2N)2[ZnBr4] or (3,5-diClPy)2ZnBr4, and 3,5-di­chloro­pyridinium tetra­bromido­cobaltate(II), (C5H4Cl2N)2[CoBr4] or (3,5-diClPy)2CoBr4, arrange according to favourable electrostatic inter­actions. Cations are preferably surrounded by anions and vice versa; rare cation–cation contacts are associated with an anti­parallel dipole orientation. N—H...X (X = Cl and Br) hydrogen bonds and X...X halogen bonds compete as closest contacts between neighbouring residues. The former dominate in the title compounds; the four symmetrically independent pyridinium N—H groups in each compound act as donors in charge-assisted hydrogen bonds, with halogen ligands and the tetra­hedral metallate anions as acceptors. The MX coordinative bonds in the latter are significantly longer if the halide ligand is engaged in a classical X...H—N hydrogen bond. In all three solids, triangular halogen-bond inter­actions are observed. They might contribute to the stabilization of the structures, but even the shortest inter­halogen contacts are only slightly shorter than the sum of the van der Waals radii.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617013201/yp3141sup1.cif
Contains datablocks a, b, c, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013201/yp3141asup2.hkl
Contains datablock a

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013201/yp3141bsup3.hkl
Contains datablock b

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617013201/yp3141csup4.hkl
Contains datablock c

CCDC references: 1544665; 1544664; 1544663

Computing details top

For all structures, data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015).

3,5-Dichloropyridinium tetrachloridozincate(II) (a) top
Crystal data top
(C5H4Cl2N)2[ZnCl4]Z = 4
Mr = 505.15F(000) = 992
Triclinic, P1Dx = 1.877 Mg m3
a = 8.6181 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.8068 (9) ÅCell parameters from 9898 reflections
c = 16.7622 (12) Åθ = 2.5–30.6°
α = 85.5267 (9)°µ = 2.56 mm1
β = 79.0539 (10)°T = 100 K
γ = 80.1701 (10)°Block, colourless
V = 1787.7 (2) Å30.22 × 0.17 × 0.15 mm
Data collection top
Bruker D8 goniometer with APEX CCD detector
diffractometer
10232 independent reflections
Radiation source: Incoatec microsource8944 reflections with I > 2σ(I)
Multilayer optics monochromatorRint = 0.030
ω scansθmax = 30.8°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1212
Tmin = 0.550, Tmax = 0.746k = 1817
27232 measured reflectionsl = 2322
Refinement top
Refinement on F24 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075 w = 1/[σ2(Fo2) + (0.0375P)2 + 0.486P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
10232 reflectionsΔρmax = 0.66 e Å3
391 parametersΔρmin = 0.81 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Zn10.04124 (2)0.78927 (2)0.39906 (2)0.01146 (5)
Cl90.26668 (5)0.86528 (4)0.39903 (3)0.01472 (9)
Cl100.14829 (5)0.85629 (3)0.50523 (3)0.01354 (8)
Cl110.09664 (5)0.61035 (3)0.41480 (3)0.01247 (8)
Cl120.03922 (5)0.84000 (3)0.27916 (2)0.01314 (8)
Zn20.36013 (2)0.29703 (2)0.14760 (2)0.01090 (5)
Cl130.59505 (5)0.36103 (3)0.14726 (2)0.01451 (9)
Cl140.17331 (5)0.35504 (3)0.25770 (2)0.01274 (8)
Cl150.41474 (5)0.11842 (3)0.15994 (3)0.01330 (8)
Cl160.27101 (5)0.35377 (3)0.03059 (2)0.01191 (8)
Cl10.26683 (5)0.88582 (4)0.02446 (3)0.01907 (9)
Cl20.86632 (5)0.86925 (4)0.08192 (3)0.01723 (9)
N10.44948 (19)0.86663 (12)0.22309 (9)0.0150 (3)
H10.412 (3)0.8646 (17)0.2745 (10)0.018*
C10.3442 (2)0.87317 (14)0.17271 (11)0.0152 (3)
H1A0.23330.87540.19350.018*
C20.4009 (2)0.87664 (13)0.08998 (11)0.0137 (3)
C30.5630 (2)0.87447 (13)0.05965 (11)0.0125 (3)
H3A0.60260.87640.00280.015*
C40.6650 (2)0.86933 (14)0.11513 (11)0.0126 (3)
C50.6072 (2)0.86510 (14)0.19792 (11)0.0151 (3)
H50.67710.86120.23590.018*
Cl30.48206 (6)0.91805 (5)0.62077 (3)0.03215 (13)
Cl40.01348 (6)0.85565 (4)0.87638 (3)0.02460 (11)
N20.02787 (19)0.90136 (12)0.64179 (10)0.0156 (3)
H20.035 (2)0.9035 (18)0.6090 (12)0.019*
C60.1787 (2)0.91230 (14)0.61020 (11)0.0164 (4)
H60.21050.92490.55330.020*
C70.2875 (2)0.90490 (15)0.66191 (12)0.0168 (4)
C80.2407 (2)0.88611 (14)0.74520 (11)0.0155 (3)
H80.31520.87990.78110.019*
C90.0816 (2)0.87680 (14)0.77386 (11)0.0145 (3)
C100.0261 (2)0.88468 (14)0.72147 (11)0.0147 (3)
H100.13510.87850.74130.018*
Cl50.58818 (5)0.38973 (4)0.23486 (3)0.01754 (9)
Cl61.16900 (6)0.41530 (4)0.16871 (3)0.02303 (10)
N30.7563 (2)0.38242 (12)0.03267 (10)0.0157 (3)
H30.719 (3)0.3781 (17)0.0183 (10)0.019*
C110.6548 (2)0.38432 (14)0.08452 (12)0.0156 (4)
H110.54470.38100.06510.019*
C120.7146 (2)0.39120 (13)0.16679 (11)0.0133 (3)
C130.8745 (2)0.39961 (14)0.19524 (11)0.0136 (3)
H130.91600.40460.25190.016*
C140.9714 (2)0.40048 (14)0.13817 (11)0.0146 (3)
C150.9111 (2)0.39063 (14)0.05576 (11)0.0157 (4)
H150.97800.38970.01660.019*
Cl70.81474 (5)0.36432 (4)0.36786 (3)0.02234 (10)
Cl80.34307 (6)0.35201 (4)0.63139 (3)0.02176 (10)
N40.35093 (19)0.37563 (13)0.39696 (10)0.0164 (3)
H40.284 (2)0.3783 (17)0.3626 (12)0.020*
C160.5047 (2)0.37287 (15)0.36260 (11)0.0168 (4)
H160.53600.37600.30510.020*
C170.6175 (2)0.36545 (14)0.41234 (11)0.0151 (3)
C180.5707 (2)0.35942 (14)0.49646 (11)0.0149 (3)
H180.64700.35440.53130.018*
C190.4098 (2)0.36094 (14)0.52803 (11)0.0131 (3)
C200.2979 (2)0.37024 (14)0.47730 (11)0.0141 (3)
H200.18720.37270.49890.017*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01202 (10)0.01198 (10)0.00960 (10)0.00156 (7)0.00063 (7)0.00023 (7)
Cl90.01479 (19)0.0199 (2)0.00991 (19)0.00718 (16)0.00090 (15)0.00166 (15)
Cl100.01211 (19)0.0162 (2)0.01127 (19)0.00156 (15)0.00111 (14)0.00354 (15)
Cl110.01197 (18)0.01097 (18)0.01310 (19)0.00017 (14)0.00071 (14)0.00035 (14)
Cl120.01343 (19)0.01568 (19)0.01026 (19)0.00194 (15)0.00345 (14)0.00205 (15)
Zn20.01249 (10)0.01006 (10)0.00948 (10)0.00175 (7)0.00050 (7)0.00001 (7)
Cl130.0154 (2)0.0198 (2)0.00902 (19)0.00795 (16)0.00117 (15)0.00195 (15)
Cl140.01179 (18)0.01463 (19)0.01057 (19)0.00144 (14)0.00104 (14)0.00206 (15)
Cl150.01467 (19)0.00950 (18)0.0150 (2)0.00072 (14)0.00224 (15)0.00025 (14)
Cl160.01421 (19)0.01203 (18)0.00923 (18)0.00133 (14)0.00293 (14)0.00136 (14)
Cl10.0155 (2)0.0210 (2)0.0219 (2)0.00470 (16)0.00650 (17)0.00312 (17)
Cl20.01146 (19)0.0251 (2)0.0139 (2)0.00222 (16)0.00096 (15)0.00228 (17)
N10.0198 (8)0.0122 (7)0.0105 (7)0.0024 (6)0.0028 (6)0.0011 (6)
C10.0138 (8)0.0105 (8)0.0190 (9)0.0025 (6)0.0023 (7)0.0015 (7)
C20.0157 (8)0.0077 (7)0.0176 (9)0.0013 (6)0.0033 (7)0.0000 (6)
C30.0155 (8)0.0097 (8)0.0110 (8)0.0015 (6)0.0004 (6)0.0002 (6)
C40.0126 (8)0.0116 (8)0.0122 (8)0.0018 (6)0.0011 (6)0.0005 (6)
C50.0190 (9)0.0126 (8)0.0135 (9)0.0021 (7)0.0029 (7)0.0008 (6)
Cl30.0155 (2)0.0511 (3)0.0268 (3)0.0098 (2)0.00344 (19)0.0089 (2)
Cl40.0206 (2)0.0403 (3)0.0112 (2)0.0064 (2)0.00051 (17)0.00352 (19)
N20.0190 (8)0.0153 (7)0.0140 (8)0.0025 (6)0.0068 (6)0.0002 (6)
C60.0208 (9)0.0140 (8)0.0115 (8)0.0006 (7)0.0011 (7)0.0012 (6)
C70.0129 (8)0.0185 (9)0.0168 (9)0.0029 (7)0.0019 (7)0.0022 (7)
C80.0151 (8)0.0167 (9)0.0146 (9)0.0027 (7)0.0031 (7)0.0012 (7)
C90.0169 (9)0.0147 (8)0.0109 (8)0.0031 (7)0.0003 (6)0.0008 (6)
C100.0139 (8)0.0142 (8)0.0152 (9)0.0024 (6)0.0005 (7)0.0003 (7)
Cl50.0165 (2)0.0171 (2)0.0200 (2)0.00340 (16)0.00535 (17)0.00050 (17)
Cl60.0148 (2)0.0381 (3)0.0162 (2)0.00791 (19)0.00123 (17)0.00305 (19)
N30.0218 (8)0.0134 (7)0.0101 (7)0.0040 (6)0.0023 (6)0.0001 (6)
C110.0172 (9)0.0097 (8)0.0183 (9)0.0025 (6)0.0016 (7)0.0015 (7)
C120.0146 (8)0.0088 (8)0.0167 (9)0.0017 (6)0.0032 (7)0.0004 (6)
C130.0163 (8)0.0109 (8)0.0125 (8)0.0011 (6)0.0012 (6)0.0000 (6)
C140.0128 (8)0.0142 (8)0.0153 (9)0.0016 (6)0.0004 (7)0.0000 (7)
C150.0186 (9)0.0137 (8)0.0142 (9)0.0020 (7)0.0021 (7)0.0003 (7)
Cl70.0132 (2)0.0240 (2)0.0256 (2)0.00157 (17)0.00490 (17)0.00111 (19)
Cl80.0210 (2)0.0317 (3)0.0108 (2)0.00418 (19)0.00029 (17)0.00184 (18)
N40.0171 (8)0.0184 (8)0.0141 (8)0.0019 (6)0.0058 (6)0.0013 (6)
C160.0182 (9)0.0160 (9)0.0132 (9)0.0009 (7)0.0012 (7)0.0006 (7)
C170.0123 (8)0.0141 (8)0.0166 (9)0.0010 (6)0.0010 (7)0.0016 (7)
C180.0137 (8)0.0154 (8)0.0154 (9)0.0020 (7)0.0036 (7)0.0022 (7)
C190.0147 (8)0.0131 (8)0.0106 (8)0.0018 (6)0.0007 (6)0.0007 (6)
C200.0133 (8)0.0129 (8)0.0152 (9)0.0025 (6)0.0002 (7)0.0005 (6)
Geometric parameters (Å, º) top
Zn1—Cl122.2615 (5)C8—C91.386 (2)
Zn1—Cl112.2646 (5)C8—H80.9500
Zn1—Cl102.2863 (5)C9—C101.381 (3)
Zn1—Cl92.3168 (5)C10—H100.9500
Zn2—Cl152.2566 (5)Cl5—C121.7236 (19)
Zn2—Cl162.2636 (5)Cl6—C141.7211 (18)
Zn2—Cl142.2863 (5)N3—C151.336 (2)
Zn2—Cl132.3091 (5)N3—C111.341 (2)
Cl1—C21.7237 (19)N3—H30.854 (15)
Cl2—C41.7181 (18)C11—C121.379 (3)
N1—C11.340 (2)C11—H110.9500
N1—C51.341 (2)C12—C131.390 (2)
N1—H10.860 (15)C13—C141.386 (3)
C1—C21.380 (3)C13—H130.9500
C1—H1A0.9500C14—C151.385 (2)
C2—C31.389 (2)C15—H150.9500
C3—C41.387 (2)Cl7—C171.7199 (18)
C3—H3A0.9500Cl8—C191.7201 (18)
C4—C51.383 (2)N4—C161.337 (2)
C5—H50.9500N4—C201.338 (2)
Cl3—C71.7186 (19)N4—H40.886 (15)
Cl4—C91.7234 (18)C16—C171.383 (3)
N2—C61.333 (2)C16—H160.9500
N2—C101.341 (2)C17—C181.391 (3)
N2—H20.841 (15)C18—C191.385 (2)
C6—C71.381 (3)C18—H180.9500
C6—H60.9500C19—C201.387 (2)
C7—C81.392 (3)C20—H200.9500
Cl12—Zn1—Cl11111.420 (17)C10—C9—C8121.15 (17)
Cl12—Zn1—Cl10110.664 (18)C10—C9—Cl4118.38 (14)
Cl11—Zn1—Cl10110.214 (17)C8—C9—Cl4120.47 (14)
Cl12—Zn1—Cl9106.721 (17)N2—C10—C9118.01 (17)
Cl11—Zn1—Cl9110.837 (17)N2—C10—H10121.0
Cl10—Zn1—Cl9106.835 (17)C9—C10—H10121.0
Cl15—Zn2—Cl16112.014 (17)C15—N3—C11123.98 (16)
Cl15—Zn2—Cl14108.093 (17)C15—N3—H3118.0 (15)
Cl16—Zn2—Cl14110.582 (17)C11—N3—H3118.0 (15)
Cl15—Zn2—Cl13107.358 (17)N3—C11—C12118.21 (17)
Cl16—Zn2—Cl13108.789 (17)N3—C11—H11120.9
Cl14—Zn2—Cl13109.945 (17)C12—C11—H11120.9
C1—N1—C5123.88 (16)C11—C12—C13120.92 (17)
C1—N1—H1117.2 (15)C11—C12—Cl5119.22 (14)
C5—N1—H1118.9 (15)C13—C12—Cl5119.86 (14)
N1—C1—C2118.41 (16)C14—C13—C12117.74 (16)
N1—C1—H1A120.8C14—C13—H13121.1
C2—C1—H1A120.8C12—C13—H13121.1
C1—C2—C3120.78 (17)C15—C14—C13120.82 (17)
C1—C2—Cl1118.93 (14)C15—C14—Cl6118.79 (14)
C3—C2—Cl1120.29 (14)C13—C14—Cl6120.39 (14)
C4—C3—C2117.85 (16)N3—C15—C14118.28 (17)
C4—C3—H3A121.1N3—C15—H15120.9
C2—C3—H3A121.1C14—C15—H15120.9
C5—C4—C3120.92 (16)C16—N4—C20124.11 (17)
C5—C4—Cl2118.72 (14)C16—N4—H4115.3 (15)
C3—C4—Cl2120.36 (13)C20—N4—H4120.5 (15)
N1—C5—C4118.16 (17)N4—C16—C17118.76 (17)
N1—C5—H5120.9N4—C16—H16120.6
C4—C5—H5120.9C17—C16—H16120.6
C6—N2—C10123.99 (17)C16—C17—C18120.15 (16)
C6—N2—H2117.0 (16)C16—C17—Cl7118.59 (14)
C10—N2—H2119.0 (16)C18—C17—Cl7121.27 (14)
N2—C6—C7118.61 (17)C19—C18—C17118.11 (17)
N2—C6—H6120.7C19—C18—H18120.9
C7—C6—H6120.7C17—C18—H18120.9
C6—C7—C8120.61 (17)C18—C19—C20120.99 (17)
C6—C7—Cl3118.40 (14)C18—C19—Cl8120.83 (14)
C8—C7—Cl3120.98 (15)C20—C19—Cl8118.18 (14)
C9—C8—C7117.63 (17)N4—C20—C19117.86 (16)
C9—C8—H8121.2N4—C20—H20121.1
C7—C8—H8121.2C19—C20—H20121.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Cl90.86 (2)2.22 (2)3.0686 (16)168 (2)
N2—H2···Cl100.84 (2)2.31 (2)3.1150 (16)160 (2)
N3—H3···Cl130.85 (2)2.23 (2)3.0842 (16)173 (2)
N4—H4···Cl140.89 (2)2.21 (2)3.0744 (17)164 (2)
3,5-Dichloropyridinium tetrabromidozincate(II) (b) top
Crystal data top
(C5H4Cl2N)2[ZnBr4]Z = 4
Mr = 682.99F(000) = 1280
Triclinic, P1Dx = 2.324 Mg m3
a = 8.8739 (15) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.469 (2) ÅCell parameters from 4319 reflections
c = 17.284 (3) Åθ = 2.5–29.4°
α = 79.539 (3)°µ = 9.99 mm1
β = 78.468 (2)°T = 100 K
γ = 76.968 (2)°Plate, colourless
V = 1951.7 (6) Å30.22 × 0.21 × 0.13 mm
Data collection top
Bruker D8 goniometer with APEX CCD detector
diffractometer
11250 independent reflections
Radiation source: Incoatec microsource8368 reflections with I > 2σ(I)
Multilayer optics monochromatorRint = 0.074
ω scansθmax = 30.9°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1212
Tmin = 0.395, Tmax = 0.746k = 1919
29870 measured reflectionsl = 2424
Refinement top
Refinement on F25 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.046H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.116 w = 1/[σ2(Fo2) + (0.010P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
11250 reflectionsΔρmax = 1.27 e Å3
391 parametersΔρmin = 1.99 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Zn10.05958 (6)0.79171 (4)0.40526 (3)0.01201 (12)
Br10.28751 (5)0.86665 (4)0.40065 (3)0.01551 (11)
Br20.13984 (5)0.85914 (4)0.51055 (3)0.01464 (11)
Br30.12069 (5)0.60734 (4)0.43019 (3)0.01329 (10)
Br40.03055 (5)0.84370 (4)0.27939 (3)0.01509 (11)
Zn20.34879 (6)0.29571 (4)0.13959 (3)0.01176 (12)
Br50.58451 (5)0.36099 (4)0.13805 (3)0.01411 (11)
Br60.15329 (5)0.34651 (4)0.25230 (3)0.01369 (10)
Br70.41323 (5)0.11121 (4)0.15856 (3)0.01391 (10)
Br80.25190 (5)0.36278 (4)0.01706 (3)0.01522 (11)
Cl10.27894 (14)0.87957 (11)0.03017 (8)0.0232 (3)
Cl20.86734 (13)0.86474 (10)0.07772 (7)0.0195 (3)
N10.4681 (5)0.8560 (3)0.2207 (2)0.0166 (9)
H10.435 (6)0.849 (4)0.2719 (13)0.020*
C10.3621 (5)0.8631 (4)0.1735 (3)0.0173 (10)
H1A0.25480.86400.19540.021*
C20.4136 (6)0.8693 (4)0.0917 (3)0.0162 (10)
C30.5702 (5)0.8686 (3)0.0606 (3)0.0137 (9)
H3A0.60620.87220.00480.016*
C40.6725 (5)0.8627 (4)0.1123 (3)0.0150 (10)
C50.6208 (6)0.8550 (4)0.1941 (3)0.0147 (10)
H50.69150.84920.23000.018*
Cl30.47673 (15)0.91479 (12)0.61979 (9)0.0309 (3)
Cl40.02785 (16)0.86516 (13)0.87811 (8)0.0313 (3)
N20.0356 (5)0.8988 (3)0.6483 (2)0.0178 (9)
H20.035 (4)0.899 (4)0.621 (3)0.021*
C60.1816 (6)0.9077 (4)0.6145 (3)0.0174 (10)
H60.21110.91750.55810.021*
C70.2886 (5)0.9022 (4)0.6637 (3)0.0153 (10)
C80.2455 (6)0.8881 (4)0.7453 (3)0.0178 (10)
H80.31900.88430.77940.021*
C90.0920 (6)0.8794 (4)0.7764 (3)0.0170 (10)
C100.0152 (6)0.8857 (4)0.7275 (3)0.0161 (10)
H100.12110.88100.74870.019*
Cl50.56835 (14)0.39666 (10)0.24218 (7)0.0203 (3)
Cl61.14594 (14)0.40033 (11)0.18870 (7)0.0212 (3)
N30.7436 (5)0.3859 (3)0.0496 (2)0.0148 (8)
H30.699 (5)0.381 (4)0.0001 (14)0.018*
C110.6414 (6)0.3890 (4)0.0981 (3)0.0166 (10)
H110.53380.38920.07750.020*
C120.6969 (5)0.3921 (4)0.1785 (3)0.0135 (9)
C130.8534 (5)0.3952 (4)0.2087 (3)0.0140 (9)
H130.89170.39830.26430.017*
C140.9526 (5)0.3935 (4)0.1552 (3)0.0128 (9)
C150.8960 (6)0.3888 (4)0.0750 (3)0.0150 (10)
H150.96320.38770.03820.018*
Cl70.78049 (14)0.36013 (11)0.35036 (8)0.0255 (3)
Cl80.34137 (16)0.37027 (12)0.61751 (7)0.0266 (3)
N40.3329 (5)0.3542 (3)0.3957 (2)0.0164 (9)
H40.262 (5)0.347 (4)0.370 (3)0.020*
C160.4796 (6)0.3541 (4)0.3566 (3)0.0170 (10)
H160.50540.35010.30110.020*
C170.5923 (5)0.3599 (4)0.3999 (3)0.0160 (10)
C180.5531 (5)0.3653 (4)0.4810 (3)0.0143 (10)
H180.62930.37010.51100.017*
C190.3989 (5)0.3634 (4)0.5171 (3)0.0142 (10)
C200.2872 (5)0.3596 (4)0.4739 (3)0.0148 (10)
H200.18110.36070.49850.018*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0136 (3)0.0098 (3)0.0128 (3)0.0051 (2)0.0011 (2)0.0003 (2)
Br10.0174 (2)0.0188 (3)0.0130 (2)0.0118 (2)0.00054 (17)0.00235 (19)
Br20.0141 (2)0.0144 (2)0.0161 (2)0.00621 (19)0.00062 (17)0.00318 (19)
Br30.0129 (2)0.0095 (2)0.0174 (2)0.00426 (18)0.00251 (17)0.00100 (18)
Br40.0158 (2)0.0151 (2)0.0150 (2)0.00501 (19)0.00526 (18)0.00182 (19)
Zn20.0141 (3)0.0099 (3)0.0116 (3)0.0055 (2)0.0017 (2)0.0007 (2)
Br50.0154 (2)0.0174 (3)0.0112 (2)0.00964 (19)0.00089 (17)0.00025 (18)
Br60.0123 (2)0.0145 (2)0.0147 (2)0.00533 (18)0.00061 (17)0.00167 (18)
Br70.0151 (2)0.0092 (2)0.0176 (2)0.00415 (18)0.00310 (18)0.00017 (18)
Br80.0173 (2)0.0151 (3)0.0147 (2)0.00643 (19)0.00597 (18)0.00190 (19)
Cl10.0181 (6)0.0250 (7)0.0284 (7)0.0092 (5)0.0099 (5)0.0036 (6)
Cl20.0143 (5)0.0265 (7)0.0168 (6)0.0066 (5)0.0019 (4)0.0016 (5)
N10.021 (2)0.013 (2)0.0127 (19)0.0057 (17)0.0034 (17)0.0029 (17)
C10.011 (2)0.007 (2)0.030 (3)0.0003 (18)0.000 (2)0.002 (2)
C20.019 (2)0.009 (2)0.022 (2)0.0032 (19)0.006 (2)0.001 (2)
C30.021 (2)0.004 (2)0.015 (2)0.0002 (18)0.0047 (19)0.0002 (18)
C40.011 (2)0.009 (2)0.022 (2)0.0047 (18)0.0037 (18)0.0003 (19)
C50.019 (2)0.010 (2)0.013 (2)0.0028 (19)0.0018 (18)0.0013 (19)
Cl30.0155 (6)0.0355 (9)0.0363 (8)0.0108 (6)0.0062 (5)0.0043 (6)
Cl40.0295 (7)0.0478 (10)0.0141 (6)0.0099 (7)0.0004 (5)0.0006 (6)
N20.020 (2)0.018 (2)0.018 (2)0.0066 (18)0.0063 (17)0.0013 (18)
C60.022 (3)0.012 (3)0.015 (2)0.003 (2)0.0007 (19)0.0007 (19)
C70.009 (2)0.012 (2)0.022 (2)0.0050 (18)0.0013 (18)0.004 (2)
C80.016 (2)0.017 (3)0.023 (3)0.008 (2)0.007 (2)0.001 (2)
C90.018 (2)0.017 (3)0.013 (2)0.004 (2)0.0017 (18)0.002 (2)
C100.013 (2)0.015 (3)0.019 (2)0.0085 (19)0.0036 (18)0.001 (2)
Cl50.0219 (6)0.0174 (6)0.0252 (6)0.0088 (5)0.0091 (5)0.0000 (5)
Cl60.0141 (6)0.0284 (7)0.0190 (6)0.0062 (5)0.0014 (5)0.0027 (5)
N30.019 (2)0.012 (2)0.0119 (19)0.0050 (17)0.0017 (16)0.0003 (17)
C110.018 (2)0.010 (2)0.022 (2)0.0060 (19)0.001 (2)0.001 (2)
C120.019 (2)0.008 (2)0.013 (2)0.0051 (19)0.0040 (18)0.0026 (18)
C130.019 (2)0.010 (2)0.015 (2)0.0053 (19)0.0037 (18)0.0000 (18)
C140.016 (2)0.007 (2)0.015 (2)0.0031 (18)0.0037 (18)0.0026 (18)
C150.020 (2)0.010 (2)0.014 (2)0.0022 (19)0.0040 (19)0.0011 (19)
Cl70.0147 (6)0.0240 (7)0.0338 (7)0.0081 (5)0.0094 (5)0.0031 (6)
Cl80.0286 (7)0.0360 (8)0.0142 (6)0.0074 (6)0.0009 (5)0.0050 (6)
N40.017 (2)0.014 (2)0.022 (2)0.0037 (17)0.0103 (17)0.0026 (18)
C160.022 (3)0.014 (3)0.012 (2)0.005 (2)0.0008 (19)0.0029 (19)
C170.013 (2)0.013 (2)0.021 (2)0.0069 (19)0.0016 (19)0.000 (2)
C180.015 (2)0.008 (2)0.021 (2)0.0084 (18)0.0056 (19)0.0039 (19)
C190.016 (2)0.014 (2)0.011 (2)0.0028 (19)0.0037 (18)0.0043 (19)
C200.014 (2)0.006 (2)0.022 (2)0.0039 (18)0.0018 (19)0.0016 (19)
Geometric parameters (Å, º) top
Zn1—Br32.3967 (8)C8—C91.384 (6)
Zn1—Br42.3986 (8)C8—H80.9500
Zn1—Br22.4198 (7)C9—C101.374 (7)
Zn1—Br12.4379 (7)C10—H100.9500
Zn2—Br82.3923 (8)Cl5—C121.721 (5)
Zn2—Br72.3975 (8)Cl6—C141.715 (5)
Zn2—Br62.4228 (7)N3—C111.342 (6)
Zn2—Br52.4389 (7)N3—C151.343 (6)
Cl1—C21.721 (5)N3—H30.866 (19)
Cl2—C41.717 (5)C11—C121.375 (6)
N1—C51.339 (6)C11—H110.9500
N1—C11.340 (6)C12—C131.389 (6)
N1—H10.870 (19)C13—C141.392 (6)
C1—C21.389 (7)C13—H130.9500
C1—H1A0.9500C14—C151.372 (6)
C2—C31.385 (7)C15—H150.9500
C3—C41.377 (6)Cl7—C171.718 (5)
C3—H3A0.9500Cl8—C191.722 (5)
C4—C51.388 (6)N4—C161.341 (6)
C5—H50.9500N4—C201.343 (6)
Cl3—C71.722 (5)N4—H40.867 (19)
Cl4—C91.725 (5)C16—C171.386 (7)
N2—C61.333 (6)C16—H160.9500
N2—C101.344 (6)C17—C181.386 (7)
N2—H20.850 (14)C18—C191.389 (6)
C6—C71.378 (7)C18—H180.9500
C6—H60.9500C19—C201.368 (6)
C7—C81.375 (7)C20—H200.9500
Br3—Zn1—Br4108.73 (3)C10—C9—C8121.2 (4)
Br3—Zn1—Br2110.52 (3)C10—C9—Cl4118.0 (4)
Br4—Zn1—Br2110.15 (3)C8—C9—Cl4120.7 (4)
Br3—Zn1—Br1111.83 (3)N2—C10—C9117.4 (4)
Br4—Zn1—Br1108.71 (3)N2—C10—H10121.3
Br2—Zn1—Br1106.87 (3)C9—C10—H10121.3
Br8—Zn2—Br7111.71 (3)C11—N3—C15124.0 (4)
Br8—Zn2—Br6110.67 (3)C11—N3—H3111 (3)
Br7—Zn2—Br6107.25 (3)C15—N3—H3125 (3)
Br8—Zn2—Br5109.17 (3)N3—C11—C12118.1 (4)
Br7—Zn2—Br5108.53 (3)N3—C11—H11121.0
Br6—Zn2—Br5109.46 (3)C12—C11—H11121.0
C5—N1—C1124.2 (4)C11—C12—C13120.7 (4)
C5—N1—H1119 (3)C11—C12—Cl5119.1 (4)
C1—N1—H1117 (3)C13—C12—Cl5120.1 (4)
N1—C1—C2118.1 (4)C12—C13—C14118.2 (4)
N1—C1—H1A120.9C12—C13—H13120.9
C2—C1—H1A120.9C14—C13—H13120.9
C3—C2—C1120.4 (4)C15—C14—C13120.4 (4)
C3—C2—Cl1120.8 (4)C15—C14—Cl6119.0 (4)
C1—C2—Cl1118.8 (4)C13—C14—Cl6120.6 (4)
C4—C3—C2118.6 (4)N3—C15—C14118.5 (4)
C4—C3—H3A120.7N3—C15—H15120.7
C2—C3—H3A120.7C14—C15—H15120.7
C3—C4—C5120.8 (4)C16—N4—C20124.6 (4)
C3—C4—Cl2121.1 (4)C16—N4—H4119 (3)
C5—C4—Cl2118.1 (4)C20—N4—H4117 (3)
N1—C5—C4117.9 (4)N4—C16—C17117.9 (4)
N1—C5—H5121.0N4—C16—H16121.0
C4—C5—H5121.0C17—C16—H16121.0
C6—N2—C10124.5 (4)C16—C17—C18120.5 (4)
C6—N2—H2122 (4)C16—C17—Cl7118.3 (4)
C10—N2—H2113 (4)C18—C17—Cl7121.3 (4)
N2—C6—C7118.1 (4)C17—C18—C19118.0 (4)
N2—C6—H6121.0C17—C18—H18121.0
C7—C6—H6121.0C19—C18—H18121.0
C8—C7—C6120.8 (4)C20—C19—C18121.5 (4)
C8—C7—Cl3121.3 (4)C20—C19—Cl8117.9 (4)
C6—C7—Cl3117.9 (4)C18—C19—Cl8120.6 (4)
C7—C8—C9118.1 (4)N4—C20—C19117.6 (4)
C7—C8—H8121.0N4—C20—H20121.2
C9—C8—H8121.0C19—C20—H20121.2
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br10.87 (2)2.37 (2)3.214 (4)164 (5)
N2—H2···Br20.85 (1)2.48 (3)3.271 (4)156 (5)
N3—H3···Br50.87 (2)2.39 (2)3.257 (4)177 (5)
N4—H4···Br60.87 (2)2.42 (3)3.231 (4)156 (5)
3,5-Dichloropyridinium tetrabromidocobaltate(II) (c) top
Crystal data top
(C5H4Cl2N)2[CoBr4]Z = 4
Mr = 676.55F(000) = 1268
Triclinic, P1Dx = 2.302 Mg m3
a = 8.8698 (9) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.4808 (13) ÅCell parameters from 4844 reflections
c = 17.2853 (17) Åθ = 2.5–30.2°
α = 79.5702 (15)°µ = 9.61 mm1
β = 78.4951 (14)°T = 100 K
γ = 76.8616 (14)°Block, blue
V = 1952.3 (3) Å30.22 × 0.17 × 0.15 mm
Data collection top
Bruker D8 goniometer with APEX CCD detector
diffractometer
8583 reflections with I > 2σ(I)
Radiation source: Incoatec microsourceRint = 0.053
ω scansθmax = 30.9°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1212
Tmin = 0.561, Tmax = 0.746k = 1919
29995 measured reflectionsl = 2423
11214 independent reflections
Refinement top
Refinement on F24 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.0271P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
11214 reflectionsΔρmax = 0.89 e Å3
391 parametersΔρmin = 1.21 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Co10.05993 (6)0.79167 (4)0.40511 (3)0.00985 (11)
Br10.28728 (4)0.86662 (3)0.40029 (2)0.01432 (9)
Br20.13994 (4)0.85904 (3)0.51033 (2)0.01341 (8)
Br30.12033 (4)0.60719 (3)0.42951 (2)0.01222 (8)
Br40.03061 (4)0.84250 (3)0.27921 (2)0.01406 (8)
Co20.35003 (6)0.29517 (4)0.14062 (3)0.00984 (11)
Br50.58580 (4)0.36028 (3)0.13844 (2)0.01302 (8)
Br60.15376 (4)0.34570 (3)0.25291 (2)0.01254 (8)
Br70.41366 (4)0.11084 (3)0.15889 (2)0.01296 (8)
Br80.25281 (4)0.36245 (3)0.01780 (2)0.01363 (8)
Cl10.27831 (12)0.87963 (8)0.02966 (7)0.0220 (2)
Cl20.86748 (11)0.86404 (8)0.07751 (6)0.0179 (2)
N10.4671 (4)0.8552 (3)0.2204 (2)0.0159 (7)
H10.435 (5)0.851 (3)0.2711 (12)0.019*
C10.3612 (5)0.8635 (3)0.1728 (2)0.0154 (8)
H1A0.25350.86530.19450.018*
C20.4116 (4)0.8692 (3)0.0922 (2)0.0136 (8)
C30.5707 (4)0.8684 (3)0.0596 (2)0.0122 (8)
H3A0.60640.87220.00380.015*
C40.6731 (4)0.8617 (3)0.1121 (2)0.0118 (8)
C50.6209 (4)0.8548 (3)0.1936 (2)0.0139 (8)
H50.69140.85000.22950.017*
Cl30.47623 (12)0.91503 (9)0.61965 (7)0.0295 (3)
Cl40.02645 (13)0.86710 (10)0.87785 (6)0.0296 (3)
N20.0341 (4)0.8987 (3)0.6480 (2)0.0147 (7)
H20.024 (4)0.899 (3)0.614 (2)0.018*
C60.1809 (5)0.9072 (3)0.6140 (2)0.0163 (8)
H60.21060.91610.55760.020*
C70.2878 (4)0.9026 (3)0.6633 (2)0.0131 (8)
C80.2443 (4)0.8890 (3)0.7455 (2)0.0145 (8)
H80.31780.88540.77950.017*
C90.0912 (5)0.8806 (3)0.7763 (2)0.0153 (8)
C100.0150 (5)0.8865 (3)0.7267 (2)0.0155 (8)
H100.12100.88210.74800.019*
Cl50.56872 (11)0.39707 (8)0.24192 (6)0.0186 (2)
Cl61.14615 (11)0.40161 (8)0.18838 (6)0.0200 (2)
N30.7442 (4)0.3856 (3)0.04924 (19)0.0153 (7)
H30.711 (5)0.383 (3)0.0022 (12)0.018*
C110.6428 (5)0.3882 (3)0.0976 (2)0.0136 (8)
H110.53570.38680.07690.016*
C120.6981 (4)0.3932 (3)0.1785 (2)0.0120 (8)
C130.8544 (4)0.3963 (3)0.2086 (2)0.0115 (7)
H130.89300.39970.26420.014*
C140.9526 (4)0.3942 (3)0.1546 (2)0.0123 (8)
C150.8965 (4)0.3887 (3)0.0743 (2)0.0145 (8)
H150.96380.38710.03750.017*
Cl70.78114 (11)0.35993 (8)0.35111 (7)0.0239 (2)
Cl80.34105 (13)0.37022 (9)0.61794 (6)0.0251 (2)
N40.3330 (4)0.3541 (3)0.3965 (2)0.0146 (7)
H40.268 (4)0.341 (3)0.370 (2)0.018*
C160.4805 (5)0.3538 (3)0.3576 (2)0.0157 (8)
H160.50660.34910.30210.019*
C170.5923 (4)0.3603 (3)0.4000 (2)0.0143 (8)
C180.5532 (4)0.3647 (3)0.4814 (2)0.0148 (8)
H180.63010.36820.51150.018*
C190.3999 (4)0.3639 (3)0.5174 (2)0.0124 (8)
C200.2886 (4)0.3592 (3)0.4739 (2)0.0132 (8)
H200.18280.35970.49850.016*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0103 (2)0.0099 (2)0.0088 (2)0.00251 (19)0.00006 (19)0.00106 (19)
Br10.01429 (19)0.0202 (2)0.01028 (19)0.00900 (15)0.00206 (14)0.00438 (15)
Br20.01159 (18)0.01538 (19)0.01270 (19)0.00298 (14)0.00239 (14)0.00505 (15)
Br30.01096 (18)0.01028 (18)0.01436 (19)0.00152 (14)0.00075 (14)0.00125 (14)
Br40.01402 (19)0.01666 (19)0.01139 (19)0.00218 (15)0.00428 (15)0.00039 (15)
Co20.0107 (2)0.0102 (2)0.0082 (2)0.00211 (19)0.00081 (19)0.00109 (19)
Br50.01312 (18)0.0186 (2)0.00827 (18)0.00699 (15)0.00055 (14)0.00195 (14)
Br60.00955 (17)0.01561 (19)0.01191 (19)0.00234 (14)0.00105 (14)0.00383 (14)
Br70.01302 (18)0.01031 (18)0.01472 (19)0.00126 (14)0.00164 (14)0.00168 (14)
Br80.01438 (19)0.01617 (19)0.01072 (19)0.00331 (15)0.00431 (15)0.00007 (15)
Cl10.0160 (5)0.0267 (6)0.0249 (6)0.0061 (4)0.0083 (4)0.0000 (4)
Cl20.0107 (4)0.0273 (5)0.0135 (5)0.0030 (4)0.0004 (4)0.0004 (4)
N10.0239 (19)0.0124 (17)0.0081 (16)0.0038 (14)0.0053 (14)0.0012 (13)
C10.0122 (19)0.0130 (19)0.019 (2)0.0032 (15)0.0021 (16)0.0006 (16)
C20.0141 (19)0.0091 (18)0.019 (2)0.0017 (14)0.0056 (16)0.0035 (15)
C30.0117 (18)0.0103 (18)0.0132 (19)0.0005 (14)0.0003 (15)0.0027 (15)
C40.0133 (18)0.0092 (18)0.0110 (18)0.0009 (14)0.0016 (15)0.0024 (14)
C50.0127 (19)0.0145 (19)0.013 (2)0.0021 (15)0.0012 (15)0.0027 (15)
Cl30.0135 (5)0.0364 (7)0.0322 (6)0.0081 (4)0.0083 (4)0.0024 (5)
Cl40.0258 (6)0.0483 (7)0.0106 (5)0.0053 (5)0.0018 (4)0.0012 (5)
N20.0144 (17)0.0158 (17)0.0153 (18)0.0026 (13)0.0054 (14)0.0030 (14)
C60.019 (2)0.0106 (19)0.014 (2)0.0010 (15)0.0039 (16)0.0024 (15)
C70.0075 (17)0.0148 (19)0.015 (2)0.0013 (14)0.0017 (15)0.0017 (15)
C80.0123 (19)0.0130 (19)0.018 (2)0.0001 (15)0.0040 (16)0.0039 (16)
C90.0143 (19)0.017 (2)0.013 (2)0.0042 (16)0.0011 (15)0.0005 (16)
C100.0116 (18)0.019 (2)0.016 (2)0.0042 (15)0.0012 (15)0.0032 (16)
Cl50.0179 (5)0.0188 (5)0.0209 (5)0.0049 (4)0.0074 (4)0.0015 (4)
Cl60.0120 (5)0.0299 (6)0.0161 (5)0.0042 (4)0.0008 (4)0.0006 (4)
N30.0193 (18)0.0165 (17)0.0070 (16)0.0027 (14)0.0031 (13)0.0003 (13)
C110.0148 (19)0.0086 (18)0.016 (2)0.0042 (14)0.0022 (15)0.0008 (15)
C120.0118 (18)0.0082 (18)0.016 (2)0.0024 (14)0.0018 (15)0.0024 (15)
C130.0104 (18)0.0100 (18)0.0121 (19)0.0003 (14)0.0005 (14)0.0017 (14)
C140.0091 (17)0.0119 (18)0.0116 (19)0.0011 (14)0.0042 (14)0.0019 (15)
C150.016 (2)0.0130 (19)0.014 (2)0.0006 (15)0.0047 (16)0.0009 (15)
Cl70.0124 (5)0.0229 (5)0.0317 (6)0.0053 (4)0.0106 (4)0.0053 (5)
Cl80.0272 (6)0.0350 (6)0.0117 (5)0.0046 (5)0.0013 (4)0.0064 (4)
N40.0140 (17)0.0162 (17)0.0170 (18)0.0037 (13)0.0078 (14)0.0039 (14)
C160.017 (2)0.0136 (19)0.0112 (19)0.0008 (15)0.0045 (15)0.0001 (15)
C170.0119 (18)0.0088 (18)0.019 (2)0.0001 (14)0.0011 (16)0.0002 (15)
C180.0137 (19)0.0118 (19)0.019 (2)0.0018 (15)0.0056 (16)0.0000 (16)
C190.0147 (19)0.0090 (18)0.0114 (19)0.0001 (14)0.0009 (15)0.0006 (14)
C200.0104 (18)0.0116 (19)0.016 (2)0.0017 (14)0.0023 (15)0.0024 (15)
Geometric parameters (Å, º) top
Co1—Br32.3989 (7)C8—C91.378 (5)
Co1—Br42.3994 (7)C8—H80.9500
Co1—Br22.4198 (6)C9—C101.376 (6)
Co1—Br12.4338 (6)C10—H100.9500
Co2—Br72.3964 (7)Cl5—C121.725 (4)
Co2—Br82.3981 (6)Cl6—C141.719 (4)
Co2—Br62.4194 (6)N3—C111.335 (5)
Co2—Br52.4363 (6)N3—C151.342 (5)
Cl1—C21.721 (4)N3—H30.876 (18)
Cl2—C41.714 (4)C11—C121.381 (5)
N1—C11.342 (5)C11—H110.9500
N1—C51.350 (5)C12—C131.388 (5)
N1—H10.861 (18)C13—C141.391 (5)
C1—C21.370 (5)C13—H130.9500
C1—H1A0.9500C14—C151.371 (5)
C2—C31.410 (5)C15—H150.9500
C3—C41.386 (5)Cl7—C171.718 (4)
C3—H3A0.9500Cl8—C191.724 (4)
C4—C51.385 (5)N4—C201.327 (5)
C5—H50.9500N4—C161.346 (5)
Cl3—C71.723 (4)N4—H40.861 (18)
Cl4—C91.724 (4)C16—C171.372 (6)
N2—C101.334 (5)C16—H160.9500
N2—C61.339 (5)C17—C181.390 (6)
N2—H20.852 (18)C18—C191.379 (5)
C6—C71.381 (6)C18—H180.9500
C6—H60.9500C19—C201.373 (5)
C7—C81.385 (5)C20—H200.9500
Br3—Co1—Br4108.04 (2)C10—C9—C8120.7 (4)
Br3—Co1—Br2110.50 (2)C10—C9—Cl4118.4 (3)
Br4—Co1—Br2110.23 (2)C8—C9—Cl4120.8 (3)
Br3—Co1—Br1112.23 (2)N2—C10—C9118.6 (4)
Br4—Co1—Br1108.85 (2)N2—C10—H10120.7
Br2—Co1—Br1106.98 (2)C9—C10—H10120.7
Br7—Co2—Br8111.37 (2)C11—N3—C15124.1 (3)
Br7—Co2—Br6107.22 (2)C11—N3—H3119 (3)
Br8—Co2—Br6110.52 (2)C15—N3—H3117 (3)
Br7—Co2—Br5108.85 (2)N3—C11—C12118.2 (3)
Br8—Co2—Br5108.88 (2)N3—C11—H11120.9
Br6—Co2—Br5109.97 (2)C12—C11—H11120.9
C1—N1—C5123.9 (3)C11—C12—C13120.8 (4)
C1—N1—H1118 (3)C11—C12—Cl5118.9 (3)
C5—N1—H1118 (3)C13—C12—Cl5120.3 (3)
N1—C1—C2118.6 (4)C12—C13—C14117.7 (3)
N1—C1—H1A120.7C12—C13—H13121.2
C2—C1—H1A120.7C14—C13—H13121.2
C1—C2—C3120.9 (4)C15—C14—C13121.0 (3)
C1—C2—Cl1119.6 (3)C15—C14—Cl6119.1 (3)
C3—C2—Cl1119.6 (3)C13—C14—Cl6119.9 (3)
C4—C3—C2117.5 (4)N3—C15—C14118.2 (4)
C4—C3—H3A121.2N3—C15—H15120.9
C2—C3—H3A121.2C14—C15—H15120.9
C3—C4—C5121.0 (4)C20—N4—C16124.1 (3)
C3—C4—Cl2120.7 (3)C20—N4—H4119 (3)
C5—C4—Cl2118.3 (3)C16—N4—H4116 (3)
N1—C5—C4118.1 (4)N4—C16—C17118.4 (4)
N1—C5—H5121.0N4—C16—H16120.8
C4—C5—H5121.0C17—C16—H16120.8
C10—N2—C6123.9 (4)C16—C17—C18120.2 (4)
C10—N2—H2123 (3)C16—C17—Cl7118.9 (3)
C6—N2—H2113 (3)C18—C17—Cl7121.0 (3)
N2—C6—C7118.0 (4)C19—C18—C17118.3 (4)
N2—C6—H6121.0C19—C18—H18120.9
C7—C6—H6121.0C17—C18—H18120.9
C6—C7—C8120.8 (4)C20—C19—C18120.9 (4)
C6—C7—Cl3118.1 (3)C20—C19—Cl8117.8 (3)
C8—C7—Cl3121.1 (3)C18—C19—Cl8121.3 (3)
C9—C8—C7118.0 (4)N4—C20—C19118.2 (3)
C9—C8—H8121.0N4—C20—H20120.9
C7—C8—H8121.0C19—C20—H20120.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br10.86 (2)2.37 (2)3.212 (3)165 (4)
N2—H2···Br20.85 (2)2.43 (2)3.261 (3)165 (4)
N3—H3···Br50.88 (2)2.39 (2)3.258 (3)169 (4)
N4—H4···Br60.86 (2)2.43 (2)3.233 (3)156 (4)
 

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