Bis[(R)-lacta­mido-κ²O,O′]boron(III) bromide

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.

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

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Computing details

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

Crystal data

C6H12BN2O4^+·Br^−	Z = 1
Mr = 266.89	F(000) = 134
Triclinic, P1	Dx = 1.571 Mg m^−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5806 (3) Å	Cell parameters from 770 reflections
b = 6.0026 (4) Å	θ = 1.0–23.3°
c = 9.7951 (6) Å	µ = 3.64 mm^−1
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) Å^3

Data collection

Nonius KappaCCD diffractometer	1461 independent reflections
Radiation source: fine-focus sealed tube	1452 reflections with I > 2σ(I)
Horizontally mounted graphite monochromator	Rint = 0.037
Detector resolution: 9 pixels mm^-1	θmax = 23.3°, θmin = 3.9°
CCD scans	h = −6→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995)'	k = −6→6
Tmin = 0.235, Tmax = 0.560	l = −10→10
2416 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.0605P)^2 + 0.06P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.084	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.54 e Å^−3
1461 reflections	Δρmin = −0.41 e Å^−3
128 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.105 (18)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 654 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.016 (10)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.0000 (1)	0.0000 (1)	0.0000 (1)	0.0536 (3)
B1	0.9166 (11)	0.5722 (10)	0.5161 (6)	0.0340 (11)
O1	1.1940 (7)	0.8210 (6)	0.5553 (3)	0.0369 (7)
N1	1.5901 (8)	1.0019 (7)	0.7207 (4)	0.0378 (9)
H1A	1.6637	1.1289	0.6819	0.045*
H1B	1.6826	0.9953	0.7958	0.045*
C1	1.3411 (9)	0.8215 (8)	0.6664 (5)	0.0303 (9)
O2	0.9316 (7)	0.4541 (6)	0.6301 (4)	0.0409 (8)
C2	1.1904 (11)	0.5898 (9)	0.7254 (6)	0.0323 (12)
H2	1.1657	0.6477	0.8192	0.039*
C3	1.3359 (11)	0.4324 (10)	0.7379 (7)	0.0477 (13)
H3A	1.2301	0.2893	0.7760	0.072*
H3B	1.5148	0.5374	0.7997	0.072*
H3C	1.3554	0.3702	0.6459	0.072*
O4	0.9170 (8)	0.4220 (7)	0.3746 (4)	0.0401 (8)
N4	0.6573 (10)	0.2649 (10)	0.1522 (5)	0.0505 (11)
H4A	0.7604	0.2030	0.1253	0.061*
H4B	0.5180	0.2449	0.0925	0.061*
C4	0.7114 (10)	0.3868 (10)	0.2812 (6)	0.0349 (12)
O5	0.6855 (7)	0.6083 (7)	0.4855 (4)	0.0428 (8)
C5	0.5472 (10)	0.5054 (9)	0.3407 (5)	0.0350 (10)
H5	0.3590	0.3699	0.3332	0.042*
C6	0.5376 (15)	0.7039 (13)	0.2693 (7)	0.0606 (16)
H6A	0.4290	0.7703	0.3107	0.091*
H6B	0.4564	0.6282	0.1701	0.091*
H6C	0.7212	0.8414	0.2809	0.091*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0425 (3)	0.0736 (4)	0.0443 (3)	0.0312 (3)	0.00584 (19)	0.0058 (2)
B1	0.025 (3)	0.040 (3)	0.034 (3)	0.014 (2)	0.004 (2)	0.007 (2)
O1	0.0327 (18)	0.0286 (15)	0.0426 (18)	0.0082 (14)	0.0065 (14)	0.0127 (13)
N1	0.032 (2)	0.0293 (19)	0.043 (2)	0.0070 (17)	0.0039 (17)	0.0122 (17)
C1	0.032 (2)	0.025 (2)	0.031 (2)	0.0125 (19)	0.0070 (19)	0.0062 (18)
O2	0.0264 (18)	0.0354 (17)	0.049 (2)	0.0044 (14)	0.0035 (15)	0.0158 (16)
C2	0.025 (3)	0.031 (2)	0.040 (3)	0.011 (2)	0.009 (2)	0.012 (2)
C3	0.037 (3)	0.042 (3)	0.070 (4)	0.018 (2)	0.015 (3)	0.027 (3)
O4	0.0262 (19)	0.0428 (19)	0.048 (2)	0.0171 (16)	0.0057 (16)	0.0019 (16)
N4	0.043 (2)	0.071 (3)	0.039 (2)	0.035 (2)	−0.0018 (19)	0.000 (2)
C4	0.023 (3)	0.037 (2)	0.038 (3)	0.012 (2)	−0.002 (2)	0.004 (2)
O5	0.0380 (19)	0.055 (2)	0.0380 (18)	0.0281 (16)	0.0058 (15)	0.0027 (15)
C5	0.026 (2)	0.045 (3)	0.039 (3)	0.019 (2)	0.010 (2)	0.011 (2)
C6	0.072 (4)	0.065 (3)	0.075 (4)	0.048 (3)	0.032 (3)	0.037 (3)

Geometric parameters (Å, º)

B1—O5	1.405 (7)	C3—H3B	0.9600
B1—O2	1.425 (7)	C3—H3C	0.9600
B1—O4	1.534 (6)	O4—C4	1.286 (7)
B1—O1	1.536 (6)	N4—C4	1.282 (8)
O1—C1	1.275 (6)	N4—H4A	0.8600
N1—C1	1.289 (6)	N4—H4B	0.8600
N1—H1A	0.8600	C4—C5	1.512 (8)
N1—H1B	0.8600	O5—C5	1.418 (6)
C1—C2	1.514 (7)	C5—C6	1.489 (8)
O2—C2	1.408 (7)	C5—H5	0.9800
C2—C3	1.506 (8)	C6—H6A	0.9600
C2—H2	0.9800	C6—H6B	0.9600
C3—H3A	0.9600	C6—H6C	0.9600
O5—B1—O2	116.8 (4)	C2—C3—H3C	109.5
O5—B1—O4	104.2 (4)	H3A—C3—H3C	109.5
O2—B1—O4	113.1 (4)	H3B—C3—H3C	109.5
O5—B1—O1	114.4 (4)	C4—O4—B1	108.2 (4)
O2—B1—O1	103.1 (4)	C4—N4—H4A	120.0
O4—B1—O1	104.8 (4)	C4—N4—H4B	120.0
C1—O1—B1	108.9 (3)	H4A—N4—H4B	120.0
C1—N1—H1A	120.0	N4—C4—O4	122.5 (5)
C1—N1—H1B	120.0	N4—C4—C5	124.9 (5)
H1A—N1—H1B	120.0	O4—C4—C5	112.6 (5)
O1—C1—N1	122.8 (4)	B1—O5—C5	112.4 (4)
O1—C1—C2	112.5 (4)	O5—C5—C6	112.7 (5)
N1—C1—C2	124.7 (4)	O5—C5—C4	102.5 (4)
C2—O2—B1	112.4 (4)	C6—C5—C4	113.4 (4)
O2—C2—C3	113.2 (4)	O5—C5—H5	109.4
O2—C2—C1	102.7 (4)	C6—C5—H5	109.4
C3—C2—C1	113.7 (4)	C4—C5—H5	109.4
O2—C2—H2	109.0	C5—C6—H6A	109.5
C3—C2—H2	109.0	C5—C6—H6B	109.5
C1—C2—H2	109.0	H6A—C6—H6B	109.5
C2—C3—H3A	109.5	C5—C6—H6C	109.5
C2—C3—H3B	109.5	H6A—C6—H6C	109.5
H3A—C3—H3B	109.5	H6B—C6—H6C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···Br1	0.86	2.53	3.289 (5)	147
N1—H1A···O2^i	0.86	2.04	2.878 (5)	164
N1—H1B···Br1^ii	0.86	2.49	3.341 (4)	173
N4—H4A···Br1^iii	0.86	2.49	3.339 (5)	169

Symmetry codes: (i) x+1, y+1, z; (ii) x+2, y+1, z+1; (iii) x+1, y, z.