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The structure of the title compound is composed of rare Z-shaped octa­bromide anions embedded within N-methyl­nicotinic acid cations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023008460/wm5697sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023008460/wm5697Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023008460/wm5697Isup3.cml
Supplementary material

CCDC reference: 2297637

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2021); cell refinement: CrysAlis PRO (Rigaku OD, 2021); data reduction: CrysAlis PRO (Rigaku OD, 2021); program(s) used to solve structure: SHELXT (Sheldrick, 2015); program(s) used to refine structure: olex2.refine (Bourhis et al., 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Bis(3-carboxy-1-methylpyridinium) octabromide top
Crystal data top
2C7H8NO2+·Br82Z = 1
Mr = 915.52F(000) = 424.594
Triclinic, P1Dx = 2.397 Mg m3
a = 6.8537 (5) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.0873 (6) ÅCell parameters from 2335 reflections
c = 14.5145 (6) Åθ = 3.2–23.7°
α = 95.746 (5)°µ = 12.67 mm1
β = 91.156 (4)°T = 293 K
γ = 115.002 (7)°Block, light red
V = 634.23 (8) Å30.17 × 0.11 × 0.06 mm
Data collection top
Xcalibur, Eos
diffractometer
1848 reflections with I 2u(I)
Detector resolution: 16.1593 pixels mm-1Rint = 0.048
ω scansθmax = 29.3°, θmin = 2.8°
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2021)
h = 89
Tmin = 0.458, Tmax = 1.000k = 99
9457 measured reflectionsl = 1919
3008 independent reflections
Refinement top
Refinement on F213 constraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.047 w = 1/[σ2(Fo2) + (0.0186P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.075(Δ/σ)max = 0.001
S = 1.02Δρmax = 1.38 e Å3
3008 reflectionsΔρmin = 1.32 e Å3
132 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0112 (5)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br20.06745 (8)0.45917 (8)0.30515 (3)0.05120 (19)
Br30.18168 (9)0.43980 (10)0.15210 (3)0.0628 (2)
Br10.29688 (10)0.47662 (9)0.43679 (4)0.0673 (2)
Br40.04755 (10)0.12253 (10)0.04613 (3)0.0781 (3)
O10.9137 (6)0.8874 (6)0.3821 (2)0.0564 (10)
O20.7895 (5)1.0613 (5)0.4839 (2)0.0540 (10)
N10.4595 (6)0.8218 (6)0.1811 (2)0.0420 (10)
C20.6297 (7)0.9597 (7)0.3314 (3)0.0348 (12)
C60.7873 (8)0.9736 (8)0.4062 (3)0.0430 (13)
C10.6035 (7)0.8341 (7)0.2488 (3)0.0423 (13)
H1a0.6851 (7)0.7580 (7)0.2398 (3)0.0507 (15)*
C40.3646 (8)1.0582 (8)0.2730 (3)0.0477 (13)
H40.2828 (8)1.1345 (8)0.2802 (3)0.0572 (16)*
C50.3421 (8)0.9306 (8)0.1928 (3)0.0497 (14)
H50.2430 (8)0.9193 (8)0.1454 (3)0.0597 (17)*
C30.5093 (8)1.0726 (8)0.3430 (3)0.0444 (13)
H30.5259 (8)1.1585 (8)0.3981 (3)0.0533 (16)*
C70.4279 (8)0.6816 (8)0.0942 (3)0.0660 (17)
H7a0.508 (4)0.600 (4)0.1002 (9)0.099 (3)*
H7b0.2774 (10)0.589 (4)0.0823 (13)0.099 (3)*
H7c0.477 (5)0.7640 (9)0.0437 (5)0.099 (3)*
H10.992 (7)0.879 (9)0.426 (3)0.099 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br20.0515 (4)0.0417 (3)0.0592 (3)0.0185 (3)0.0015 (2)0.0076 (2)
Br30.0686 (4)0.0771 (5)0.0512 (3)0.0412 (3)0.0081 (3)0.0013 (3)
Br10.0787 (5)0.0529 (4)0.0661 (4)0.0265 (3)0.0223 (3)0.0019 (3)
Br40.0779 (5)0.0717 (5)0.0592 (4)0.0069 (4)0.0200 (3)0.0140 (3)
O10.057 (3)0.077 (3)0.047 (2)0.042 (2)0.0104 (17)0.0010 (19)
O20.057 (2)0.072 (3)0.0359 (18)0.036 (2)0.0069 (15)0.0123 (17)
N10.039 (3)0.046 (3)0.036 (2)0.015 (2)0.0041 (18)0.0001 (19)
C20.029 (3)0.040 (3)0.032 (2)0.012 (2)0.0030 (19)0.006 (2)
C60.038 (3)0.045 (3)0.049 (3)0.021 (3)0.002 (2)0.005 (3)
C10.035 (3)0.045 (3)0.043 (3)0.014 (2)0.002 (2)0.004 (2)
C40.049 (3)0.053 (3)0.051 (3)0.032 (3)0.002 (2)0.004 (3)
C50.045 (3)0.063 (4)0.041 (3)0.024 (3)0.007 (2)0.009 (3)
C30.048 (3)0.044 (3)0.039 (3)0.019 (3)0.001 (2)0.002 (2)
C70.074 (4)0.078 (4)0.041 (3)0.034 (3)0.018 (3)0.020 (3)
Geometric parameters (Å, º) top
Br2—Br32.7307 (7)C2—C11.380 (6)
Br2—Br12.4095 (7)C2—C31.373 (6)
Br3—Br43.0625 (10)C1—H1a0.9300
Br1—Br1i3.1813 (12)C4—H40.9300
Br4—Br4ii2.4002 (15)C4—C51.365 (6)
O1—C61.290 (6)C4—C31.370 (6)
O1—H10.845 (19)C5—H50.9300
O2—C61.228 (5)C3—H30.9300
N1—C11.348 (5)C7—H7a0.9600
N1—C51.332 (6)C7—H7b0.9600
N1—C71.476 (5)C7—H7c0.9600
C2—C61.483 (6)
Br1—Br2—Br3178.04 (3)H1a—C1—C2120.0 (3)
Br4—Br3—Br290.37 (2)C5—C4—H4120.4 (3)
Br1i—Br1—Br2162.42 (4)C3—C4—H4120.4 (3)
Br4ii—Br4—Br3176.22 (3)C3—C4—C5119.2 (5)
H1—O1—C6116 (4)C4—C5—N1121.2 (4)
C5—N1—C1120.7 (4)H5—C5—N1119.4 (3)
C7—N1—C1119.4 (4)H5—C5—C4119.4 (3)
C7—N1—C5119.8 (4)C4—C3—C2119.8 (4)
C1—C2—C6120.3 (5)H3—C3—C2120.1 (3)
C3—C2—C6120.6 (4)H3—C3—C4120.1 (3)
C3—C2—C1119.2 (4)H7a—C7—N1109.5
O2—C6—O1125.2 (4)H7b—C7—N1109.5
C2—C6—O1114.6 (4)H7b—C7—H7a109.5
C2—C6—O2120.1 (5)H7c—C7—N1109.5
C2—C1—N1120.0 (5)H7c—C7—H7a109.5
H1a—C1—N1120.0 (3)H7c—C7—H7b109.5
O1—C6—C2—C19.9 (5)N1—C1—C2—C6179.8 (4)
O1—C6—C2—C3169.6 (4)N1—C1—C2—C30.6 (5)
O2—C6—C2—C1169.9 (4)N1—C5—C4—C30.7 (6)
O2—C6—C2—C310.6 (5)C2—C3—C4—C50.3 (5)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2iii0.80 (7)1.89 (7)2.668 (5)164 (7)
C1—H1A···Br3iv0.932.963.838 (5)158
C5—H5···Br4v0.932.993.881 (5)160
C7—H7A···Br3iv0.962.923.857 (6)166
Symmetry codes: (iii) x+2, y+2, z+1; (iv) x+1, y, z; (v) x, y+1, z.
 

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