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The title Schiff base compound, C9H9Br2NO2, synthesized by the reaction of 3,5-dibromo-2-hydroxy­benzaldehyde and 2-amino­ethanol in ethanol solution, crystallizes in a zwitterionic form. The mol­ecule adopts a trans configuration about the central C=N bond. In the crystal structure, O—H...O inter­molecular hydrogen bonds link the mol­ecules into ribbons along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806036245/ci2161sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806036245/ci2161Isup2.hkl
Contains datablock I

CCDC reference: 624171

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.024
  • wR factor = 0.055
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.82 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.14 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br1 .. 3.55 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br1 .. 3.55 Ang. PLAT731_ALERT_1_C Bond Calc 0.90(3), Rep 0.897(10) ...... 3.00 su-Ra N1 -H1 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.90(3), Rep 0.897(10) ...... 3.00 su-Ra N1 -H1 1.555 1.555 PLAT737_ALERT_1_C D...A Calc 2.867(5), Rep 2.867(2) ...... 2.50 su-Ra O2 -O2 1.555 8.544
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 0.821 Tmax scaled 0.334 Tmin scaled 0.091 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 26.49 From the CIF: _reflns_number_total 2139 Count of symmetry unique reflns 1202 Completeness (_total/calc) 177.95% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 937 Fraction of Friedel pairs measured 0.780 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2002); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

2,4-Dibromo-6-(2-hydroxyethyliminiomethyl)phenolate top
Crystal data top
C9H9Br2NO2F(000) = 1248
Mr = 322.99Dx = 2.079 Mg m3
Orthorhombic, Aba2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2acCell parameters from 5840 reflections
a = 18.7541 (9) Åθ = 2.2–28.0°
b = 21.9752 (11) ŵ = 7.83 mm1
c = 5.0082 (3) ÅT = 295 K
V = 2064.01 (19) Å3Prism, yellow
Z = 80.50 × 0.14 × 0.14 mm
Data collection top
Bruker APEX area-detector
diffractometer
2139 independent reflections
Radiation source: fine-focus sealed tube2009 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
φ and ω scansθmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2323
Tmin = 0.111, Tmax = 0.407k = 2727
10642 measured reflectionsl = 66
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.024 w = 1/[σ2(Fo2) + (0.0326P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.055(Δ/σ)max = 0.001
S = 1.00Δρmax = 0.92 e Å3
2139 reflectionsΔρmin = 0.43 e Å3
132 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.0081 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 936 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.027 (12)
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
Br10.182769 (15)0.613447 (14)1.30996 (10)0.03181 (11)
Br20.149288 (18)0.802597 (14)0.56070 (10)0.04049 (12)
O10.04484 (12)0.56934 (10)1.0547 (6)0.0357 (5)
O20.21279 (12)0.58027 (10)0.8007 (7)0.0390 (5)
H20.23250.59100.66240.058*
N10.05429 (15)0.56737 (14)0.7025 (6)0.0306 (6)
H10.0301 (17)0.5503 (14)0.838 (5)0.037*
C10.06596 (17)0.62026 (15)0.9490 (7)0.0270 (7)
C20.12788 (15)0.65041 (14)1.0364 (7)0.0253 (6)
C30.15150 (18)0.70450 (14)0.9295 (7)0.0291 (7)
H30.19240.72320.99550.035*
C40.11343 (17)0.73072 (14)0.7222 (7)0.0293 (7)
C50.05276 (18)0.70377 (14)0.6237 (7)0.0299 (8)
H50.02760.72200.48500.036*
C60.02896 (16)0.64877 (14)0.7331 (6)0.0268 (7)
C70.03116 (17)0.61829 (15)0.6153 (7)0.0316 (8)
H70.05400.63630.47050.038*
C80.11121 (16)0.53393 (15)0.5721 (9)0.0367 (8)
H8A0.12600.55570.41320.044*
H8B0.09350.49440.51720.044*
C90.17480 (17)0.52545 (15)0.7544 (8)0.0352 (10)
H9A0.15850.50930.92410.042*
H9B0.20680.49580.67570.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02552 (16)0.03797 (19)0.03196 (16)0.00023 (13)0.00313 (17)0.00580 (16)
Br20.0421 (2)0.02756 (19)0.0518 (2)0.00430 (14)0.0025 (2)0.00851 (18)
O10.0333 (12)0.0303 (12)0.0435 (13)0.0074 (10)0.0049 (13)0.0074 (13)
O20.0330 (11)0.0374 (13)0.0465 (13)0.0038 (10)0.0026 (15)0.0093 (14)
N10.0230 (15)0.0306 (16)0.0381 (14)0.0010 (12)0.0036 (11)0.0017 (11)
C10.0204 (16)0.0263 (17)0.0343 (17)0.0002 (13)0.0060 (13)0.0027 (13)
C20.0213 (13)0.0270 (16)0.0276 (15)0.0028 (11)0.0026 (14)0.0022 (14)
C30.0257 (18)0.0269 (18)0.0347 (17)0.0020 (14)0.0022 (14)0.0028 (14)
C40.0265 (16)0.0229 (16)0.0386 (18)0.0027 (14)0.0039 (13)0.0014 (13)
C50.0236 (16)0.0297 (18)0.037 (2)0.0066 (13)0.0012 (13)0.0042 (13)
C60.0188 (15)0.0280 (17)0.0336 (19)0.0007 (14)0.0012 (11)0.0012 (12)
C70.0221 (16)0.0397 (19)0.0328 (19)0.0036 (14)0.0029 (13)0.0018 (13)
C80.0268 (16)0.0360 (19)0.0472 (19)0.0040 (14)0.0002 (18)0.0148 (19)
C90.0260 (16)0.0318 (18)0.048 (3)0.0038 (15)0.0043 (15)0.0035 (15)
Geometric parameters (Å, º) top
Br1—C21.896 (3)C3—H30.93
Br2—C41.898 (3)C4—C51.374 (5)
O1—C11.300 (4)C5—C61.400 (4)
O2—C91.419 (4)C5—H50.93
O2—H20.82C6—C71.438 (5)
N1—C71.277 (5)C7—H70.93
N1—C81.451 (4)C8—C91.514 (5)
N1—H10.897 (10)C8—H8A0.97
C1—C21.407 (4)C8—H8B0.97
C1—C61.429 (5)C9—H9A0.97
C2—C31.377 (4)C9—H9B0.97
C3—C41.386 (5)
C9—O2—H2109.5C5—C6—C1121.3 (3)
C7—N1—C8122.7 (3)C5—C6—C7119.4 (3)
C7—N1—H1117 (2)C1—C6—C7119.1 (3)
C8—N1—H1120 (2)N1—C7—C6122.3 (3)
O1—C1—C2122.0 (3)N1—C7—H7118.9
O1—C1—C6122.5 (3)C6—C7—H7118.9
C2—C1—C6115.5 (3)N1—C8—C9111.7 (3)
C3—C2—C1123.4 (3)N1—C8—H8A109.3
C3—C2—Br1118.4 (2)C9—C8—H8A109.3
C1—C2—Br1118.1 (2)N1—C8—H8B109.3
C2—C3—C4119.0 (3)C9—C8—H8B109.3
C2—C3—H3120.5H8A—C8—H8B107.9
C4—C3—H3120.5O2—C9—C8112.9 (3)
C5—C4—C3121.1 (3)O2—C9—H9A109.0
C5—C4—Br2119.9 (3)C8—C9—H9A109.0
C3—C4—Br2118.9 (2)O2—C9—H9B109.0
C4—C5—C6119.7 (3)C8—C9—H9B109.0
C4—C5—H5120.1H9A—C9—H9B107.8
C6—C5—H5120.1
O1—C1—C2—C3179.7 (3)C4—C5—C6—C7175.0 (3)
C6—C1—C2—C31.6 (5)O1—C1—C6—C5179.7 (3)
O1—C1—C2—Br11.9 (4)C2—C1—C6—C51.5 (4)
C6—C1—C2—Br1176.9 (2)O1—C1—C6—C74.3 (5)
C1—C2—C3—C41.0 (5)C2—C1—C6—C7174.4 (3)
Br1—C2—C3—C4177.4 (2)C8—N1—C7—C6175.0 (3)
C2—C3—C4—C50.3 (5)C5—C6—C7—N1178.4 (3)
C2—C3—C4—Br2176.2 (2)C1—C6—C7—N12.4 (5)
C3—C4—C5—C60.3 (5)C7—N1—C8—C9119.2 (4)
Br2—C4—C5—C6176.1 (2)N1—C8—C9—O271.0 (4)
C4—C5—C6—C11.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.90 (1)1.83 (2)2.563 (4)138 (3)
O2—H2···O2i0.822.102.867 (2)157
Symmetry code: (i) x+1/2, y, z1/2.
 

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