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The title compound, C7H7N2+·Br, forms a layered solid with each cation forming three strong and one weaker C—H...Br hydrogen bonds within the layer. All atoms except two of the methyl H atoms lie on a mirror plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006264/hg6136sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006264/hg6136Isup2.hkl
Contains datablock I

CCDC reference: 270428

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.063
  • Data-to-parameter ratio = 101.2

checkCIF/PLATON results

No syntax errors found



Alert level A REFLT03_ALERT_3_A Reflection count > 15% excess reflns - sys abs data present? From the CIF: _diffrn_reflns_theta_max 27.74 From the CIF: _diffrn_reflns_theta_full 0.00 From the CIF: _reflns_number_total 6277 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1054 Completeness (_total/calc) 595.54%
Author Response: ...Crystal was twinned so final refinement was performed with a SHELX HKLF5-type multicomponent file. Such a refinement with SHELXL requires that no merging of equivalent reflections be performed. This is to avoid averaging symmetry equivalent reflections with differing contributions from the two twin components. This is the reason for the "excess reflections". This is addressed in the _publ_section_exptl_refinement section.
PLAT021_ALERT_1_A Ratio Unique / Expected Reflections too High ...       5.95
Author Response: ...Same as previous response.

Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C3 - C7 .. 8.09 su
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.96 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C7 ... 1.44 Ang.
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

3-cyano-N-methylpyridinium bromide top
Crystal data top
C7H7N2+·BrF(000) = 196
Mr = 199.06Dx = 1.600 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 4284 reflections
a = 8.109 (1) Åθ = 2.7–28.2°
b = 6.6266 (8) ŵ = 4.90 mm1
c = 8.381 (1) ÅT = 100 K
β = 113.406 (2)°Plate, colorless
V = 413.30 (9) Å30.16 × 0.11 × 0.01 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
6277 independent reflections
Radiation source: fine-focus sealed tube5502 reflections with I > 2σ(I)
Graphite monochromatorθmax = 27.7°, θmin = 2.7°
φ and ω scansh = 1010
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2003)
k = 88
Tmin = 0.515, Tmax = 0.948l = 1010
6277 measured reflections
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)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0295P)2]
where P = (Fo2 + 2Fc2)/3
6277 reflections(Δ/σ)max = 0.002
62 parametersΔρmax = 1.15 e Å3
0 restraintsΔρmin = 0.39 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
Br0.16283 (3)0.25000.39522 (2)0.02087 (6)
N10.72977 (19)0.25000.57911 (18)0.0178 (3)
N21.3436 (2)0.25000.9680 (2)0.0384 (4)
C10.6408 (2)0.25000.3861 (2)0.0271 (5)
H1A0.51650.25000.36400.041*
H1B0.68130.13440.35500.041*
C20.9091 (2)0.25000.6533 (2)0.0201 (4)
H20.97670.25000.58310.024*
C30.9959 (2)0.25000.8321 (2)0.0199 (4)
C40.8981 (2)0.25000.9360 (2)0.0233 (4)
H40.95680.25001.05930.028*
C50.7118 (2)0.25000.8537 (2)0.0262 (4)
H50.64080.25000.92060.031*
C60.6307 (2)0.25000.6754 (2)0.0230 (4)
H60.50320.25000.61940.028*
C71.1898 (3)0.25000.9081 (2)0.0245 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br0.02230 (10)0.01909 (9)0.01987 (10)0.0000.00694 (8)0.000
N10.0194 (8)0.0151 (7)0.0162 (8)0.0000.0042 (7)0.000
N20.0243 (10)0.0581 (12)0.0323 (10)0.0000.0108 (8)0.000
C10.0287 (12)0.0273 (10)0.0215 (10)0.0000.0059 (9)0.000
C20.0219 (9)0.0162 (9)0.0268 (11)0.0000.0146 (8)0.000
C30.0171 (10)0.0167 (8)0.0226 (10)0.0000.0044 (8)0.000
C40.0254 (10)0.0228 (9)0.0186 (10)0.0000.0055 (8)0.000
C50.0246 (10)0.0291 (10)0.0273 (12)0.0000.0128 (9)0.000
C60.0159 (9)0.0232 (9)0.0257 (11)0.0000.0037 (8)0.000
C70.0284 (12)0.0227 (9)0.0228 (10)0.0000.0105 (9)0.000
Geometric parameters (Å, º) top
N1—C21.335 (2)C3—C41.392 (2)
N1—C61.346 (2)C3—C71.442 (2)
N1—C11.487 (2)C4—C51.389 (2)
N2—C71.145 (2)C4—H40.95
C1—H1A0.95C5—C61.373 (2)
C1—H1B0.91C5—H50.95
C2—C31.380 (2)C6—H60.95
C2—H20.95
C2—N1—C6121.34 (15)C4—C3—C7121.05 (17)
C2—N1—C1118.32 (16)C5—C4—C3117.84 (18)
C6—N1—C1120.34 (14)C5—C4—H4121.1
N1—C1—H1A103.3C3—C4—H4121.1
N1—C1—H1B103.7C6—C5—C4119.80 (18)
H1A—C1—H1B114.8C6—C5—H5120.1
N1—C2—C3119.80 (17)C4—C5—H5120.1
N1—C2—H2120.1N1—C6—C5120.68 (16)
C3—C2—H2120.1N1—C6—H6119.7
C2—C3—C4120.53 (17)C5—C6—H6119.7
C2—C3—C7118.42 (17)N2—C7—C3179.8 (2)
Close-contact parameters for (I) (Å, °), with corrected values in parentheses top
H···..AD···..AD—H···..A
C1—H1A···..Br2.98 [2.85]3.907 (1)164 [165]
C2—H2···..Bri2.58 [2.44]3.528 (1)179 [180]
C4—H4···..Brii2.64 [2.51]3.585 (1)172 [172]
C6—H6···..Br2.65 [2.52]3.582 (1)166 [166[
C5—H5···..N2iii2.59 [2.47]3.479 (2)154 [155]
Symmetry codes: (i) 1+x, y, z. (ii) 1+x, y, 1+z. (iii) x-1, y, z.
 

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