Download citation
Download citation
link to html
The title compound, C6H12BN2O4+·Br, contains one monomeric tetra­coordinated boron complex cation, [B(C3H6NO2)2]+, and one Br anion. The B coordination occurs via the amide and oxide O atoms [average B—O = 1.535 (6) and 1.415 (7) Å, respectively] and may be described as a distorted tetra­hedral arrangement, with O—B—O angles in the range 104.2 (4)–116.8 (4)°. In the crystal structure, the cations and anions are linked by N—H...Br and N—H...O hydrogen bonds, generating a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027158/gw2009sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027158/gw2009Isup2.hkl
Contains datablock I

CCDC reference: 654935

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.032
  • wR factor = 0.084
  • Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 23.26 Deg.
Alert level B THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5556 PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6]..... 23.26 Deg.
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.24 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 1.241 Tmax scaled 0.695 Tmin scaled 0.292 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 23.26 From the CIF: _reflns_number_total 1461 Count of symmetry unique reflns 807 Completeness (_total/calc) 181.04% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 654 Fraction of Friedel pairs measured 0.810 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Bruker–Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Farrugia, 1999).

Bis[(R)-lactamido-κ2O,O']boron(III) bromide top
Crystal data top
C6H12BN2O4+·BrZ = 1
Mr = 266.89F(000) = 134
Triclinic, P1Dx = 1.571 Mg m3
Hall symbol: P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.5806 (3) ÅCell parameters from 770 reflections
b = 6.0026 (4) Åθ = 1.0–23.3°
c = 9.7951 (6) ŵ = 3.64 mm1
α = 98.823 (3)°T = 293 K
β = 97.302 (4)°Parallelepiped, colourless
γ = 116.858 (3)°0.35 × 0.30 × 0.10 mm
V = 281.99 (3) Å3
Data collection top
Nonius KappaCCD
diffractometer
1461 independent reflections
Radiation source: fine-focus sealed tube1452 reflections with I > 2σ(I)
Horizontally mounted graphite monochromatorRint = 0.037
Detector resolution: 9 pixels mm-1θmax = 23.3°, θmin = 3.9°
CCD scansh = 65
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996; Blessing, 1995)'
k = 66
Tmin = 0.235, Tmax = 0.560l = 1010
2416 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032 w = 1/[σ2(Fo2) + (0.0605P)2 + 0.06P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.084(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.54 e Å3
1461 reflectionsΔρmin = 0.41 e Å3
128 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.105 (18)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 654 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.016 (10)
Special details top

Experimental. Crystals suitable for X-ray diffraction were difficult to obtain.

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
Br10.0000 (1)0.0000 (1)0.0000 (1)0.0536 (3)
B10.9166 (11)0.5722 (10)0.5161 (6)0.0340 (11)
O11.1940 (7)0.8210 (6)0.5553 (3)0.0369 (7)
N11.5901 (8)1.0019 (7)0.7207 (4)0.0378 (9)
H1A1.66371.12890.68190.045*
H1B1.68260.99530.79580.045*
C11.3411 (9)0.8215 (8)0.6664 (5)0.0303 (9)
O20.9316 (7)0.4541 (6)0.6301 (4)0.0409 (8)
C21.1904 (11)0.5898 (9)0.7254 (6)0.0323 (12)
H21.16570.64770.81920.039*
C31.3359 (11)0.4324 (10)0.7379 (7)0.0477 (13)
H3A1.23010.28930.77600.072*
H3B1.51480.53740.79970.072*
H3C1.35540.37020.64590.072*
O40.9170 (8)0.4220 (7)0.3746 (4)0.0401 (8)
N40.6573 (10)0.2649 (10)0.1522 (5)0.0505 (11)
H4A0.76040.20300.12530.061*
H4B0.51800.24490.09250.061*
C40.7114 (10)0.3868 (10)0.2812 (6)0.0349 (12)
O50.6855 (7)0.6083 (7)0.4855 (4)0.0428 (8)
C50.5472 (10)0.5054 (9)0.3407 (5)0.0350 (10)
H50.35900.36990.33320.042*
C60.5376 (15)0.7039 (13)0.2693 (7)0.0606 (16)
H6A0.42900.77030.31070.091*
H6B0.45640.62820.17010.091*
H6C0.72120.84140.28090.091*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0425 (3)0.0736 (4)0.0443 (3)0.0312 (3)0.00584 (19)0.0058 (2)
B10.025 (3)0.040 (3)0.034 (3)0.014 (2)0.004 (2)0.007 (2)
O10.0327 (18)0.0286 (15)0.0426 (18)0.0082 (14)0.0065 (14)0.0127 (13)
N10.032 (2)0.0293 (19)0.043 (2)0.0070 (17)0.0039 (17)0.0122 (17)
C10.032 (2)0.025 (2)0.031 (2)0.0125 (19)0.0070 (19)0.0062 (18)
O20.0264 (18)0.0354 (17)0.049 (2)0.0044 (14)0.0035 (15)0.0158 (16)
C20.025 (3)0.031 (2)0.040 (3)0.011 (2)0.009 (2)0.012 (2)
C30.037 (3)0.042 (3)0.070 (4)0.018 (2)0.015 (3)0.027 (3)
O40.0262 (19)0.0428 (19)0.048 (2)0.0171 (16)0.0057 (16)0.0019 (16)
N40.043 (2)0.071 (3)0.039 (2)0.035 (2)0.0018 (19)0.000 (2)
C40.023 (3)0.037 (2)0.038 (3)0.012 (2)0.002 (2)0.004 (2)
O50.0380 (19)0.055 (2)0.0380 (18)0.0281 (16)0.0058 (15)0.0027 (15)
C50.026 (2)0.045 (3)0.039 (3)0.019 (2)0.010 (2)0.011 (2)
C60.072 (4)0.065 (3)0.075 (4)0.048 (3)0.032 (3)0.037 (3)
Geometric parameters (Å, º) top
B1—O51.405 (7)C3—H3B0.9600
B1—O21.425 (7)C3—H3C0.9600
B1—O41.534 (6)O4—C41.286 (7)
B1—O11.536 (6)N4—C41.282 (8)
O1—C11.275 (6)N4—H4A0.8600
N1—C11.289 (6)N4—H4B0.8600
N1—H1A0.8600C4—C51.512 (8)
N1—H1B0.8600O5—C51.418 (6)
C1—C21.514 (7)C5—C61.489 (8)
O2—C21.408 (7)C5—H50.9800
C2—C31.506 (8)C6—H6A0.9600
C2—H20.9800C6—H6B0.9600
C3—H3A0.9600C6—H6C0.9600
O5—B1—O2116.8 (4)C2—C3—H3C109.5
O5—B1—O4104.2 (4)H3A—C3—H3C109.5
O2—B1—O4113.1 (4)H3B—C3—H3C109.5
O5—B1—O1114.4 (4)C4—O4—B1108.2 (4)
O2—B1—O1103.1 (4)C4—N4—H4A120.0
O4—B1—O1104.8 (4)C4—N4—H4B120.0
C1—O1—B1108.9 (3)H4A—N4—H4B120.0
C1—N1—H1A120.0N4—C4—O4122.5 (5)
C1—N1—H1B120.0N4—C4—C5124.9 (5)
H1A—N1—H1B120.0O4—C4—C5112.6 (5)
O1—C1—N1122.8 (4)B1—O5—C5112.4 (4)
O1—C1—C2112.5 (4)O5—C5—C6112.7 (5)
N1—C1—C2124.7 (4)O5—C5—C4102.5 (4)
C2—O2—B1112.4 (4)C6—C5—C4113.4 (4)
O2—C2—C3113.2 (4)O5—C5—H5109.4
O2—C2—C1102.7 (4)C6—C5—H5109.4
C3—C2—C1113.7 (4)C4—C5—H5109.4
O2—C2—H2109.0C5—C6—H6A109.5
C3—C2—H2109.0C5—C6—H6B109.5
C1—C2—H2109.0H6A—C6—H6B109.5
C2—C3—H3A109.5C5—C6—H6C109.5
C2—C3—H3B109.5H6A—C6—H6C109.5
H3A—C3—H3B109.5H6B—C6—H6C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4B···Br10.862.533.289 (5)147
N1—H1A···O2i0.862.042.878 (5)164
N1—H1B···Br1ii0.862.493.341 (4)173
N4—H4A···Br1iii0.862.493.339 (5)169
Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+1, z+1; (iii) x+1, y, z.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds