Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The structure of the phenanthroline-derived boronic acid viologen, C20H18BN2O2+·Br·CH3OH, as a methanol solvate, was determined as part of a fluorescence quenching study. There is –π stacking of the phenanthroline rings and hydrogen bonding involving Br ions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001369/na6280sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001369/na6280Isup2.hkl
Contains datablock I

CCDC reference: 234910

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.096
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELXL97.

N-[2-(Hydroxymethoxyboryl)benzyl]-4,7-phenanthrolinium bromide methanol solvate top
Crystal data top
C20H18BN2O2+·BrCH4OF(000) = 904
Mr = 441.13Dx = 1.468 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 545 reflections
a = 16.376 (3) Åθ = 2.5–25°
b = 13.894 (3) ŵ = 2.08 mm1
c = 9.0289 (15) ÅT = 90 K
β = 103.723 (4)°Plate, colorless
V = 1995.7 (7) Å30.18 × 0.11 × 0.05 mm
Z = 4
Data collection top
Bruker SMART 1000
diffractometer
3618 independent reflections
Radiation source: normal-focus sealed tube2624 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.061
Detector resolution: 8.3 pixels mm-1θmax = 25.3°, θmin = 2.0°
ω scansh = 1919
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
k = 1616
Tmin = 0.705, Tmax = 0.903l = 1010
11491 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)] = 0.042Hydrogen site location: difference Fourier map
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0382P)2]
where P = (Fo2 + 2Fc2)/3
3618 reflections(Δ/σ)max < 0.001
261 parametersΔρmax = 0.53 e Å3
0 restraintsΔρmin = 0.63 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
Br10.78239 (2)0.58393 (3)0.31425 (4)0.01940 (13)
O10.48970 (18)0.5484 (2)0.2154 (3)0.0303 (7)
H1A0.527 (3)0.585 (3)0.263 (5)0.036*
O20.35007 (16)0.49847 (19)0.1386 (3)0.0202 (6)
N10.16625 (18)0.5979 (2)0.3377 (3)0.0148 (7)
N20.03533 (19)0.6233 (2)0.2513 (3)0.0177 (7)
C10.1151 (2)0.6048 (2)0.1921 (4)0.0147 (8)
C20.1491 (2)0.5906 (3)0.0625 (4)0.0163 (8)
H20.20730.57740.07540.020*
C30.0978 (2)0.5959 (3)0.0794 (4)0.0173 (8)
H30.12060.58430.16520.021*
C40.0103 (2)0.6184 (3)0.1035 (4)0.0148 (8)
C50.1165 (2)0.6429 (3)0.2732 (4)0.0185 (9)
H50.14920.64690.37510.022*
C60.1570 (2)0.6582 (3)0.1548 (4)0.0184 (8)
H60.21550.67210.17720.022*
C70.1117 (2)0.6527 (3)0.0063 (4)0.0165 (8)
H70.13840.66240.07520.020*
C80.0252 (2)0.6327 (3)0.0235 (4)0.0134 (8)
C90.0285 (2)0.6249 (3)0.1754 (4)0.0126 (8)
C100.0025 (2)0.6338 (3)0.3078 (4)0.0157 (8)
H100.06060.64620.29830.019*
C110.0500 (2)0.6249 (3)0.4498 (4)0.0170 (8)
H110.02880.63040.53870.020*
C120.1347 (2)0.6077 (3)0.4614 (4)0.0179 (9)
H120.17150.60260.55970.021*
C130.2583 (2)0.5821 (3)0.3617 (4)0.0162 (8)
H13A0.26820.52780.29720.019*
H13B0.28210.56440.46950.019*
C140.3028 (2)0.6715 (3)0.3228 (4)0.0159 (8)
C150.2760 (2)0.7617 (3)0.3585 (4)0.0203 (9)
H150.22880.76640.40220.024*
C160.3167 (2)0.8446 (3)0.3318 (4)0.0219 (9)
H160.29700.90570.35520.026*
C170.3865 (2)0.8383 (3)0.2708 (4)0.0250 (9)
H170.41490.89500.25180.030*
C180.4146 (2)0.7483 (3)0.2375 (4)0.0238 (9)
H180.46350.74450.19840.029*
C190.3733 (2)0.6624 (3)0.2598 (4)0.0169 (8)
B10.4074 (3)0.5655 (3)0.2051 (5)0.0221 (10)
C200.3772 (3)0.4130 (3)0.0738 (4)0.0272 (9)
H20C0.42120.42980.02130.041*
H20A0.32940.38440.00070.041*
H20B0.39950.36660.15510.041*
O30.60938 (18)0.6693 (2)0.3600 (3)0.0324 (7)
H3A0.663 (3)0.644 (3)0.349 (5)0.039*
C210.6140 (3)0.6727 (4)0.5192 (5)0.0405 (12)
H21A0.61550.60700.55920.061*
H21B0.56470.70630.53700.061*
H21C0.66510.70700.57100.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0177 (2)0.0239 (2)0.01666 (19)0.00196 (19)0.00435 (14)0.00002 (19)
O10.0200 (16)0.0284 (17)0.0426 (19)0.0021 (13)0.0077 (14)0.0105 (14)
O20.0211 (14)0.0209 (15)0.0194 (14)0.0024 (12)0.0062 (11)0.0012 (12)
N10.0157 (15)0.0162 (18)0.0133 (15)0.0012 (13)0.0050 (12)0.0010 (13)
N20.0211 (18)0.0181 (17)0.0131 (16)0.0050 (14)0.0029 (14)0.0022 (13)
C10.0172 (19)0.011 (2)0.0154 (18)0.0020 (14)0.0019 (15)0.0018 (14)
C20.0163 (18)0.017 (2)0.0168 (18)0.0001 (17)0.0072 (15)0.0013 (17)
C30.022 (2)0.021 (2)0.0126 (17)0.0055 (17)0.0108 (15)0.0036 (16)
C40.018 (2)0.0120 (19)0.0146 (18)0.0009 (15)0.0039 (16)0.0033 (15)
C50.023 (2)0.016 (2)0.0131 (19)0.0046 (17)0.0018 (16)0.0021 (16)
C60.0153 (19)0.014 (2)0.024 (2)0.0005 (16)0.0023 (16)0.0004 (17)
C70.0171 (19)0.019 (2)0.0146 (18)0.0007 (16)0.0051 (16)0.0018 (16)
C80.0190 (19)0.0112 (19)0.0097 (17)0.0004 (15)0.0026 (15)0.0002 (14)
C90.0143 (18)0.0132 (19)0.0124 (18)0.0019 (15)0.0072 (15)0.0007 (14)
C100.0138 (19)0.018 (2)0.0164 (19)0.0025 (16)0.0047 (15)0.0003 (16)
C110.021 (2)0.019 (2)0.0142 (19)0.0007 (16)0.0105 (16)0.0006 (16)
C120.025 (2)0.018 (2)0.0114 (18)0.0016 (16)0.0061 (16)0.0007 (15)
C130.0171 (18)0.018 (2)0.0149 (17)0.0022 (17)0.0063 (15)0.0005 (17)
C140.0111 (19)0.022 (2)0.0107 (18)0.0007 (15)0.0041 (15)0.0010 (16)
C150.020 (2)0.025 (2)0.0174 (19)0.0002 (17)0.0064 (16)0.0001 (16)
C160.023 (2)0.019 (2)0.019 (2)0.0036 (18)0.0043 (17)0.0020 (17)
C170.021 (2)0.023 (2)0.028 (2)0.0053 (18)0.0003 (18)0.0020 (19)
C180.0139 (19)0.028 (2)0.030 (2)0.0010 (17)0.0049 (17)0.0014 (19)
C190.0154 (19)0.019 (2)0.0142 (19)0.0034 (16)0.0003 (15)0.0016 (16)
B10.026 (3)0.023 (3)0.019 (2)0.004 (2)0.009 (2)0.0048 (19)
C200.030 (2)0.029 (2)0.023 (2)0.007 (2)0.0065 (18)0.002 (2)
O30.0258 (16)0.040 (2)0.0306 (16)0.0043 (14)0.0056 (14)0.0022 (14)
C210.044 (3)0.056 (3)0.024 (2)0.006 (2)0.013 (2)0.010 (2)
Geometric parameters (Å, º) top
O1—B11.349 (5)C11—C121.386 (5)
O1—H1A0.83 (5)C11—H110.9500
O2—B11.357 (5)C12—H120.9500
O2—C201.440 (5)C13—C141.524 (5)
N1—C121.345 (4)C13—H13A0.9900
N1—C11.384 (4)C13—H13B0.9900
N1—C131.487 (4)C14—C151.391 (5)
N2—C51.326 (5)C14—C191.408 (5)
N2—C41.368 (4)C15—C161.381 (5)
C1—C91.418 (5)C15—H150.9500
C1—C21.424 (5)C16—C171.384 (5)
C2—C31.357 (5)C16—H160.9500
C2—H20.9500C17—C181.390 (6)
C3—C41.433 (5)C17—H170.9500
C3—H30.9500C18—C191.409 (5)
C4—C81.416 (5)C18—H180.9500
C5—C61.401 (5)C19—B11.582 (6)
C5—H50.9500C20—H20C0.9800
C6—C71.372 (5)C20—H20A0.9800
C6—H60.9500C20—H20B0.9800
C7—C81.406 (5)O3—C211.422 (5)
C7—H70.9500O3—H3A0.98 (4)
C8—C91.447 (5)C21—H21A0.9800
C9—C101.410 (5)C21—H21B0.9800
C10—C111.370 (5)C21—H21C0.9800
C10—H100.9500
B1—O1—H1A122 (3)C11—C12—H12119.0
B1—O2—C20119.8 (3)N1—C13—C14111.7 (3)
C12—N1—C1121.1 (3)N1—C13—H13A109.3
C12—N1—C13118.0 (3)C14—C13—H13A109.3
C1—N1—C13120.9 (3)N1—C13—H13B109.3
C5—N2—C4116.9 (3)C14—C13—H13B109.3
N1—C1—C9118.7 (3)H13A—C13—H13B108.0
N1—C1—C2120.2 (3)C15—C14—C19120.6 (4)
C9—C1—C2121.1 (3)C15—C14—C13119.1 (3)
C3—C2—C1119.6 (3)C19—C14—C13120.2 (3)
C3—C2—H2120.2C16—C15—C14121.3 (3)
C1—C2—H2120.2C16—C15—H15119.4
C2—C3—C4121.8 (3)C14—C15—H15119.4
C2—C3—H3119.1C15—C16—C17119.7 (4)
C4—C3—H3119.1C15—C16—H16120.1
N2—C4—C8123.3 (3)C17—C16—H16120.1
N2—C4—C3117.0 (3)C16—C17—C18119.3 (4)
C8—C4—C3119.7 (3)C16—C17—H17120.3
N2—C5—C6123.8 (3)C18—C17—H17120.3
N2—C5—H5118.1C17—C18—C19122.4 (4)
C6—C5—H5118.1C17—C18—H18118.8
C7—C6—C5119.5 (3)C19—C18—H18118.8
C7—C6—H6120.2C18—C19—C14116.7 (4)
C5—C6—H6120.2C18—C19—B1117.3 (3)
C6—C7—C8119.0 (3)C14—C19—B1125.9 (3)
C6—C7—H7120.5O1—B1—O2119.0 (4)
C8—C7—H7120.5O1—B1—C19123.3 (4)
C7—C8—C4117.4 (3)O2—B1—C19117.6 (4)
C7—C8—C9123.6 (3)O2—C20—H20C109.5
C4—C8—C9118.9 (3)O2—C20—H20A109.5
C10—C9—C1118.6 (3)H20C—C20—H20A109.5
C10—C9—C8122.5 (3)O2—C20—H20B109.5
C1—C9—C8118.8 (3)H20C—C20—H20B109.5
C11—C10—C9120.8 (3)H20A—C20—H20B109.5
C11—C10—H10119.6C21—O3—H3A106 (3)
C9—C10—H10119.6O3—C21—H21A109.5
C10—C11—C12118.8 (3)O3—C21—H21B109.5
C10—C11—H11120.6H21A—C21—H21B109.5
C12—C11—H11120.6O3—C21—H21C109.5
N1—C12—C11122.0 (3)H21A—C21—H21C109.5
N1—C12—H12119.0H21B—C21—H21C109.5
C12—N1—C1—C91.7 (5)C1—C9—C10—C111.1 (5)
C13—N1—C1—C9176.8 (3)C8—C9—C10—C11179.2 (3)
C12—N1—C1—C2177.6 (3)C9—C10—C11—C120.6 (5)
C13—N1—C1—C24.0 (5)C1—N1—C12—C110.0 (5)
N1—C1—C2—C3178.9 (3)C13—N1—C12—C11178.5 (3)
C9—C1—C2—C30.3 (5)C10—C11—C12—N11.1 (6)
C1—C2—C3—C42.0 (6)C12—N1—C13—C14106.7 (3)
C5—N2—C4—C80.4 (5)C1—N1—C13—C1471.8 (4)
C5—N2—C4—C3179.1 (3)N1—C13—C14—C1537.5 (4)
C2—C3—C4—N2179.1 (3)N1—C13—C14—C19146.2 (3)
C2—C3—C4—C82.1 (5)C19—C14—C15—C160.8 (5)
C4—N2—C5—C60.3 (5)C13—C14—C15—C16177.1 (3)
N2—C5—C6—C70.1 (6)C14—C15—C16—C171.2 (5)
C5—C6—C7—C80.5 (5)C15—C16—C17—C180.1 (6)
C6—C7—C8—C40.4 (5)C16—C17—C18—C191.8 (6)
C6—C7—C8—C9179.7 (3)C17—C18—C19—C142.1 (5)
N2—C4—C8—C70.0 (5)C17—C18—C19—B1175.2 (4)
C3—C4—C8—C7178.8 (3)C15—C14—C19—C180.8 (5)
N2—C4—C8—C9179.4 (3)C13—C14—C19—C18175.4 (3)
C3—C4—C8—C90.6 (5)C15—C14—C19—B1176.2 (3)
N1—C1—C9—C102.2 (5)C13—C14—C19—B17.5 (5)
C2—C1—C9—C10177.0 (3)C20—O2—B1—O13.1 (5)
N1—C1—C9—C8179.6 (3)C20—O2—B1—C19174.1 (3)
C2—C1—C9—C81.1 (5)C18—C19—B1—O136.2 (5)
C7—C8—C9—C102.2 (6)C14—C19—B1—O1146.8 (4)
C4—C8—C9—C10177.1 (3)C18—C19—B1—O2140.9 (4)
C7—C8—C9—C1179.7 (3)C14—C19—B1—O236.1 (5)
C4—C8—C9—C10.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O30.83 (5)1.84 (5)2.674 (4)178 (5)
O3—H3A···Br10.97 (5)2.22 (5)3.187 (3)177 (4)
C12—H12···Br1i0.952.863.425 (4)119
C10—H10···Br1ii0.952.753.604 (4)150
C13—H13A···O20.992.223.017 (5)137
C11—H11···N2iii0.952.383.320 (5)172
Symmetry codes: (i) x+1, y+1, z+1; (ii) x1, y, z; (iii) x, y, z+1.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

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