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The title compound, C6H10N3O2+·BF4, crystallizes with one histidinium cation and one tetra­fluoro­borate anion in the asymmetric unit. The protonated cation and the deprotonated anion are linked through a number of inter­molecular N—H...O and N—H...F hydrogen bonds, forming a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806006192/hg6303sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806006192/hg6303Isup2.hkl
Contains datablock I

CCDC reference: 285490

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.025
  • wR factor = 0.067
  • Data-to-parameter ratio = 5.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT089_ALERT_3_B Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 5.07 PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.31 Ratio
Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for B1 PLAT350_ALERT_3_C Short C-H Bond (0.96A) C2 - H2 ... 0.84 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 B F4
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 67.88 From the CIF: _reflns_number_total 903 Count of symmetry unique reflns 903 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1988); cell refinement: CAD-4 Software; data reduction: XCAD4 in WinGX (Farrugia, 1999); program(s) used to solve structure: SIR92 in WinGX; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-32 in WinGX; software used to prepare material for publication: SHELXL97.

L-Histidinium tetrafluoroborate ? top
Crystal data top
C6H10N3O2+·BF4F(000) = 248
Mr = 242.98Dx = 1.732 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ybCell parameters from 25 reflections
a = 5.0259 (8) Åθ = 20–30°
b = 9.089 (2) ŵ = 1.59 mm1
c = 10.218 (2) ÅT = 293 K
β = 93.482 (15)°Prism, colourless
V = 465.91 (17) Å30.3 × 0.2 × 0.2 mm
Z = 2
Data collection top
Enraf-Nonius CAD-4
diffractometer
902 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
Graphite monochromatorθmax = 67.9°, θmin = 4.3°
ω–2θ scansh = 06
Absorption correction: ψ scan
(North et al., 1968)
k = 010
Tmin = 0.661, Tmax = 0.727l = 1212
1008 measured reflections2 standard reflections every 60 min
903 independent reflections intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.067 w = 1/[σ2(Fo2) + (0.0343P)2 + 0.1648P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
903 reflectionsΔρmax = 0.16 e Å3
178 parametersΔρmin = 0.15 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.088 (4)
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
C10.9070 (6)0.4571 (3)0.3540 (3)0.0372 (6)
C21.1016 (5)0.2416 (3)0.3552 (2)0.0330 (6)
C30.8821 (5)0.2334 (3)0.2719 (2)0.0268 (5)
C40.7733 (5)0.1089 (3)0.1904 (2)0.0300 (5)
H4A0.61380.07210.22810.036*
H4B0.90320.02990.19300.036*
C50.7052 (4)0.1515 (3)0.0472 (2)0.0220 (5)
C60.5759 (4)0.0196 (2)0.0249 (2)0.0238 (5)
N11.1117 (5)0.3823 (3)0.4042 (2)0.0378 (6)
N20.7618 (4)0.3695 (3)0.2748 (2)0.0309 (5)
N30.9469 (4)0.2021 (2)0.0164 (2)0.0261 (5)
O10.7086 (3)0.0548 (2)0.10060 (17)0.0327 (4)
O20.3388 (3)0.0050 (2)0.00061 (18)0.0343 (5)
F10.4664 (4)0.0904 (2)0.39713 (17)0.0487 (5)
F20.5355 (4)0.2560 (3)0.2368 (2)0.0657 (6)
F30.1214 (3)0.2125 (3)0.29443 (19)0.0565 (5)
F40.4099 (5)0.3312 (2)0.4355 (2)0.0639 (6)
B10.3837 (6)0.2222 (4)0.3410 (3)0.0341 (7)
H3C1.015 (6)0.286 (4)0.018 (3)0.033 (8)*
H3A1.083 (6)0.137 (4)0.007 (3)0.034 (8)*
H2'0.614 (6)0.398 (5)0.225 (3)0.044 (9)*
H3B0.887 (7)0.235 (5)0.100 (4)0.058 (10)*
H21.219 (6)0.179 (4)0.376 (3)0.042 (9)*
H10.887 (8)0.560 (6)0.366 (4)0.069 (12)*
H1'1.235 (7)0.408 (5)0.451 (3)0.049 (10)*
H50.589 (5)0.228 (3)0.039 (2)0.016 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0502 (16)0.0292 (14)0.0312 (13)0.0013 (12)0.0043 (11)0.0044 (12)
C20.0326 (13)0.0376 (15)0.0279 (12)0.0032 (12)0.0053 (9)0.0008 (11)
C30.0311 (12)0.0261 (13)0.0230 (10)0.0015 (10)0.0002 (8)0.0024 (9)
C40.0380 (13)0.0226 (12)0.0289 (12)0.0035 (11)0.0031 (9)0.0015 (10)
C50.0225 (11)0.0166 (11)0.0261 (11)0.0014 (9)0.0043 (8)0.0007 (9)
C60.0255 (11)0.0170 (11)0.0278 (11)0.0014 (9)0.0077 (8)0.0017 (9)
N10.0393 (12)0.0445 (15)0.0285 (10)0.0091 (11)0.0064 (9)0.0076 (11)
N20.0364 (11)0.0274 (12)0.0280 (10)0.0024 (9)0.0069 (8)0.0004 (9)
N30.0273 (11)0.0193 (9)0.0313 (11)0.0027 (9)0.0007 (8)0.0014 (9)
O10.0343 (9)0.0251 (9)0.0388 (9)0.0012 (7)0.0033 (7)0.0093 (8)
O20.0245 (9)0.0263 (9)0.0516 (11)0.0026 (7)0.0016 (7)0.0049 (8)
F10.0666 (11)0.0326 (9)0.0452 (9)0.0092 (9)0.0114 (8)0.0040 (8)
F20.0608 (11)0.0783 (16)0.0578 (11)0.0004 (11)0.0031 (8)0.0233 (12)
F30.0426 (9)0.0632 (13)0.0611 (11)0.0021 (9)0.0181 (8)0.0001 (11)
F40.0856 (14)0.0417 (11)0.0605 (12)0.0097 (10)0.0262 (10)0.0185 (10)
B10.0364 (15)0.0302 (16)0.0341 (15)0.0031 (13)0.0098 (11)0.0016 (13)
Geometric parameters (Å, º) top
C1—N11.311 (4)C5—H50.91 (3)
C1—N21.322 (4)C6—O11.251 (3)
C1—H10.95 (5)C6—O21.252 (3)
C2—C31.354 (4)N1—H1'0.79 (4)
C2—N11.373 (4)N2—H2'0.91 (3)
C2—H20.83 (4)N3—H3C0.90 (4)
C3—N21.378 (3)N3—H3A0.90 (4)
C3—C41.489 (3)N3—H3B0.93 (4)
C4—C51.532 (3)F1—B11.381 (4)
C4—H4A0.9700F2—B11.382 (4)
C4—H4B0.9700F3—B11.377 (3)
C5—N31.485 (3)F4—B11.384 (4)
C5—C61.531 (3)
N1—C1—N2108.5 (3)O1—C6—O2125.2 (2)
N1—C1—H1123 (3)O1—C6—C5119.6 (2)
N2—C1—H1128 (3)O2—C6—C5115.2 (2)
C3—C2—N1106.9 (3)C1—N1—C2109.3 (2)
C3—C2—H2131 (3)C1—N1—H1'131 (3)
N1—C2—H2122 (3)C2—N1—H1'120 (3)
C2—C3—N2106.2 (2)C1—N2—C3109.1 (2)
C2—C3—C4130.6 (2)C1—N2—H2'125 (3)
N2—C3—C4123.2 (2)C3—N2—H2'126 (3)
C3—C4—C5113.3 (2)C5—N3—H3C113 (2)
C3—C4—H4A108.9C5—N3—H3A113 (2)
C5—C4—H4A108.9H3C—N3—H3A104 (3)
C3—C4—H4B108.9C5—N3—H3B106 (2)
C5—C4—H4B108.9H3C—N3—H3B100 (3)
H4A—C4—H4B107.7H3A—N3—H3B120 (3)
N3—C5—C6111.52 (18)F3—B1—F1110.2 (3)
N3—C5—C4110.79 (19)F3—B1—F2108.0 (2)
C6—C5—C4108.99 (19)F1—B1—F2110.3 (3)
N3—C5—H5105.0 (16)F3—B1—F4109.6 (3)
C6—C5—H5108.0 (16)F1—B1—F4108.5 (2)
C4—C5—H5112.5 (15)F2—B1—F4110.2 (3)
N1—C2—C3—N21.2 (3)N3—C5—C6—O2161.8 (2)
N1—C2—C3—C4179.4 (2)C4—C5—C6—O275.6 (3)
C2—C3—C4—C5130.8 (3)N2—C1—N1—C20.7 (3)
N2—C3—C4—C549.9 (3)C3—C2—N1—C10.3 (3)
C3—C4—C5—N361.3 (3)N1—C1—N2—C31.4 (3)
C3—C4—C5—C6175.68 (19)C2—C3—N2—C11.6 (3)
N3—C5—C6—O118.8 (3)C4—C3—N2—C1178.9 (2)
C4—C5—C6—O1103.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3C···O1i0.90 (4)2.14 (4)3.010 (3)161 (3)
N3—H3A···O2ii0.90 (4)1.82 (4)2.722 (3)174 (3)
N2—H2···O1iii0.91 (3)2.04 (3)2.953 (3)174 (3)
N3—H3B···F3iii0.93 (4)2.05 (4)2.945 (3)161 (3)
N1—H1···F1iv0.79 (4)2.09 (4)2.856 (3)161 (4)
Symmetry codes: (i) x+2, y+1/2, z; (ii) x+1, y, z; (iii) x+1, y+1/2, z; (iv) x+2, y+1/2, z+1.
 

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