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The title compound, C9H10BrNO3, which exists as the E isomer, crystallizes with two independent mol­ecules in the asymmetric unit. The bond lengths and angles in both mol­ecules are normal. The crystal packing is stabilized by inter­molecular O—H...O hydrogen bonds, which link the mol­ecules into circular tetra­mers, and by weak π–π stacking inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601364X/cv2032sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680601364X/cv2032Isup2.hkl
Contains datablock I

CCDC reference: 608414

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.044
  • wR factor = 0.107
  • Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.85 PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT230_ALERT_2_C Hirshfeld Test Diff for O3 - N1 .. 5.68 su
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 0.850 Tmax scaled 0.373 Tmin scaled 0.296
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

(E)-2-Bromo-4,5-dimethoxybenzaldehyde oxime top
Crystal data top
C9H10BrNO3F(000) = 1040
Mr = 260.09Dx = 1.664 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1048 reflections
a = 8.0870 (14) Åθ = 2.3–22.3°
b = 9.6175 (17) ŵ = 3.94 mm1
c = 26.795 (5) ÅT = 291 K
β = 94.964 (3)°Block, colourless
V = 2076.2 (6) Å30.34 × 0.31 × 0.25 mm
Z = 8
Data collection top
Bruker SMART CCD area-detector
diffractometer
3653 independent reflections
Radiation source: fine-focus sealed tube2458 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
φ and ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 98
Tmin = 0.348, Tmax = 0.439k = 1111
10481 measured reflectionsl = 3129
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0506P)2 + 0.3059P]
where P = (Fo2 + 2Fc2)/3
3653 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = 0.40 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
Br10.34024 (6)0.09276 (5)0.424220 (19)0.06379 (19)
Br20.14045 (6)0.33461 (6)0.274671 (19)0.0723 (2)
O10.3145 (4)0.0338 (3)0.14501 (12)0.0607 (8)
O20.0363 (4)0.0329 (3)0.09324 (11)0.0633 (8)
O30.4377 (4)0.4071 (4)0.19438 (13)0.0820 (11)
H3A0.52280.41150.17410.123*
O40.3386 (4)0.1673 (3)0.40163 (11)0.0624 (8)
O50.2648 (4)0.0223 (4)0.34159 (12)0.0678 (9)
O60.3021 (4)0.2738 (4)0.55941 (12)0.0802 (10)
H6A0.26880.33430.57890.120*
N10.3275 (5)0.3143 (4)0.17702 (14)0.0584 (10)
N20.1758 (4)0.2446 (4)0.52174 (13)0.0565 (10)
C10.0968 (5)0.2226 (4)0.21647 (15)0.0468 (10)
C20.2250 (5)0.1370 (4)0.20384 (16)0.0500 (11)
H2B0.32830.13630.22370.060*
C30.2006 (5)0.0531 (4)0.16212 (16)0.0461 (10)
C40.0460 (5)0.0547 (4)0.13376 (16)0.0437 (10)
C50.0766 (5)0.1407 (4)0.14686 (15)0.0437 (10)
H5A0.17970.14210.12700.052*
C60.0546 (5)0.2269 (4)0.18889 (15)0.0424 (10)
C70.4756 (6)0.0393 (6)0.17205 (19)0.0713 (14)
H7A0.54550.10600.15590.107*
H7B0.46450.06870.20660.107*
H7C0.52700.05300.17210.107*
C80.1177 (6)0.0412 (6)0.06386 (19)0.0749 (15)
H8A0.10840.10720.03640.112*
H8B0.14730.05070.05010.112*
H8C0.20380.07290.08480.112*
C90.1911 (6)0.3184 (4)0.20140 (17)0.0527 (11)
H9A0.17380.38140.22860.063*
C100.1271 (5)0.0052 (4)0.42097 (16)0.0481 (11)
C110.0129 (5)0.0487 (5)0.38285 (16)0.0525 (11)
H11A0.04150.11940.36040.063*
C120.1412 (5)0.0103 (4)0.37763 (15)0.0479 (11)
C130.1806 (5)0.1147 (4)0.41042 (16)0.0484 (11)
C140.0672 (5)0.1555 (4)0.44870 (16)0.0496 (11)
H14A0.09730.22460.47160.060*
C150.0923 (5)0.0972 (4)0.45466 (15)0.0451 (10)
C160.2379 (7)0.1353 (6)0.3082 (2)0.0884 (18)
H16A0.33630.14740.28460.133*
H16B0.14150.11480.28970.133*
H16C0.21740.22090.32760.133*
C170.3923 (6)0.2650 (6)0.43598 (19)0.0751 (15)
H17A0.50650.29310.42550.113*
H17B0.38790.22300.46940.113*
H17C0.31970.34670.43690.113*
C180.2108 (5)0.1445 (5)0.49550 (17)0.0516 (11)
H18A0.31450.09860.50190.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0507 (3)0.0681 (3)0.0717 (4)0.0100 (2)0.0005 (2)0.0010 (3)
Br20.0573 (3)0.0884 (4)0.0688 (4)0.0097 (3)0.0086 (3)0.0238 (3)
O10.0454 (19)0.0646 (19)0.070 (2)0.0136 (16)0.0073 (16)0.0066 (17)
O20.052 (2)0.073 (2)0.062 (2)0.0043 (16)0.0151 (16)0.0174 (18)
O30.056 (2)0.112 (3)0.076 (2)0.024 (2)0.0061 (18)0.014 (2)
O40.0454 (19)0.078 (2)0.063 (2)0.0087 (16)0.0003 (15)0.0030 (18)
O50.056 (2)0.084 (2)0.061 (2)0.0068 (17)0.0121 (17)0.0069 (19)
O60.069 (2)0.090 (3)0.078 (2)0.0052 (19)0.0160 (19)0.027 (2)
N10.046 (2)0.062 (2)0.069 (3)0.0171 (19)0.013 (2)0.010 (2)
N20.052 (2)0.063 (3)0.051 (2)0.001 (2)0.0135 (19)0.001 (2)
C10.043 (3)0.049 (2)0.047 (3)0.009 (2)0.002 (2)0.002 (2)
C20.038 (3)0.053 (3)0.057 (3)0.005 (2)0.010 (2)0.001 (2)
C30.040 (3)0.046 (2)0.051 (3)0.000 (2)0.003 (2)0.008 (2)
C40.044 (3)0.039 (2)0.047 (3)0.003 (2)0.002 (2)0.003 (2)
C50.032 (2)0.048 (2)0.050 (3)0.0014 (19)0.0067 (19)0.012 (2)
C60.040 (2)0.045 (2)0.041 (2)0.0029 (19)0.0002 (19)0.003 (2)
C70.043 (3)0.093 (4)0.076 (3)0.012 (3)0.007 (2)0.001 (3)
C80.058 (3)0.088 (4)0.076 (4)0.003 (3)0.011 (3)0.029 (3)
C90.053 (3)0.054 (3)0.050 (3)0.003 (2)0.004 (2)0.001 (2)
C100.043 (3)0.055 (3)0.046 (3)0.000 (2)0.000 (2)0.010 (2)
C110.049 (3)0.056 (3)0.052 (3)0.001 (2)0.004 (2)0.001 (2)
C120.048 (3)0.056 (3)0.038 (2)0.006 (2)0.004 (2)0.001 (2)
C130.038 (2)0.056 (3)0.051 (3)0.002 (2)0.002 (2)0.013 (2)
C140.048 (3)0.053 (3)0.049 (3)0.005 (2)0.008 (2)0.003 (2)
C150.044 (3)0.047 (2)0.044 (2)0.001 (2)0.001 (2)0.007 (2)
C160.098 (5)0.073 (4)0.087 (4)0.002 (3)0.035 (3)0.015 (3)
C170.054 (3)0.096 (4)0.076 (4)0.023 (3)0.008 (3)0.011 (3)
C180.040 (3)0.056 (3)0.058 (3)0.002 (2)0.000 (2)0.006 (2)
Geometric parameters (Å, º) top
Br1—C101.913 (4)C6—C91.473 (6)
Br2—C11.903 (4)C7—H7A0.9800
O1—C31.353 (5)C7—H7B0.9800
O1—C71.436 (5)C7—H7C0.9800
O2—C41.371 (5)C8—H8A0.9800
O2—C81.417 (5)C8—H8B0.9800
O3—N11.370 (4)C8—H8C0.9800
O3—H3A0.8400C9—H9A0.9500
O4—C131.375 (5)C10—C111.381 (6)
O4—C171.410 (6)C10—C151.381 (6)
O5—C121.365 (5)C10—Br11.913 (4)
O5—C161.436 (6)C11—C121.366 (6)
O6—N21.401 (4)C11—H11A0.9500
O6—H6A0.8400C12—C131.389 (6)
N1—C91.233 (5)C13—C141.373 (6)
N2—C181.239 (5)C14—C151.403 (6)
C1—C61.375 (5)C14—H14A0.9500
C1—C21.388 (6)C15—C181.463 (6)
C1—Br21.903 (4)C16—H16A0.9800
C2—C31.379 (6)C16—H16B0.9800
C2—H2B0.9500C16—H16C0.9800
C3—C41.406 (6)C17—H17A0.9800
C4—C51.360 (6)C17—H17B0.9800
C5—C61.398 (5)C17—H17C0.9800
C5—H5A0.9500C18—H18A0.9500
C3—O1—C7117.8 (4)H8B—C8—H8C109.5
C4—O2—C8117.5 (3)N1—C9—C6121.0 (4)
N1—O3—H3A109.5N1—C9—H9A119.5
C13—O4—C17117.8 (4)C6—C9—H9A119.5
C12—O5—C16118.3 (4)C11—C10—C15122.6 (4)
N2—O6—H6A109.5C11—C10—Br1116.2 (3)
C9—N1—O3112.2 (4)C15—C10—Br1121.2 (3)
C18—N2—O6112.1 (4)C11—C10—Br1116.2 (3)
C6—C1—C2122.4 (4)C15—C10—Br1121.2 (3)
C6—C1—Br2121.1 (3)C12—C11—C10119.7 (4)
C2—C1—Br2116.5 (3)C12—C11—H11A120.1
C6—C1—Br2121.1 (3)C10—C11—H11A120.1
C2—C1—Br2116.5 (3)O5—C12—C11125.6 (4)
C3—C2—C1119.1 (4)O5—C12—C13114.8 (4)
C3—C2—H2B120.4C11—C12—C13119.5 (4)
C1—C2—H2B120.4C14—C13—O4125.0 (4)
O1—C3—C2125.6 (4)C14—C13—C12120.3 (4)
O1—C3—C4115.1 (4)O4—C13—C12114.7 (4)
C2—C3—C4119.3 (4)C13—C14—C15121.3 (4)
C5—C4—O2125.8 (4)C13—C14—H14A119.4
C5—C4—C3120.1 (4)C15—C14—H14A119.4
O2—C4—C3114.1 (4)C10—C15—C14116.6 (4)
C4—C5—C6121.6 (4)C10—C15—C18123.6 (4)
C4—C5—H5A119.2C14—C15—C18119.8 (4)
C6—C5—H5A119.2O5—C16—H16A109.5
C1—C6—C5117.4 (4)O5—C16—H16B109.5
C1—C6—C9123.1 (4)H16A—C16—H16B109.5
C5—C6—C9119.5 (4)O5—C16—H16C109.5
O1—C7—H7A109.5H16A—C16—H16C109.5
O1—C7—H7B109.5H16B—C16—H16C109.5
H7A—C7—H7B109.5O4—C17—H17A109.5
O1—C7—H7C109.5O4—C17—H17B109.5
H7A—C7—H7C109.5H17A—C17—H17B109.5
H7B—C7—H7C109.5O4—C17—H17C109.5
O2—C8—H8A109.5H17A—C17—H17C109.5
O2—C8—H8B109.5H17B—C17—H17C109.5
H8A—C8—H8B109.5N2—C18—C15119.9 (4)
O2—C8—H8C109.5N2—C18—H18A120.0
H8A—C8—H8C109.5C15—C18—H18A120.0
C6—C1—C2—C30.0 (6)C15—C10—C11—C120.1 (6)
Br2—C1—C2—C3179.8 (3)Br1—C10—C11—C12179.1 (3)
Br2—C1—C2—C3179.8 (3)Br1—C10—C11—C12179.1 (3)
C7—O1—C3—C20.5 (6)C16—O5—C12—C115.1 (6)
C7—O1—C3—C4179.4 (4)C16—O5—C12—C13176.0 (4)
C1—C2—C3—O1179.1 (4)C10—C11—C12—O5179.6 (4)
C1—C2—C3—C40.8 (6)C10—C11—C12—C130.7 (6)
C8—O2—C4—C53.9 (6)C17—O4—C13—C143.7 (6)
C8—O2—C4—C3177.6 (4)C17—O4—C13—C12174.7 (4)
O1—C3—C4—C5178.5 (4)O5—C12—C13—C14179.2 (4)
C2—C3—C4—C51.4 (6)C11—C12—C13—C141.9 (6)
O1—C3—C4—O20.1 (5)O5—C12—C13—O40.7 (5)
C2—C3—C4—O2180.0 (4)C11—C12—C13—O4179.7 (4)
O2—C4—C5—C6179.7 (4)O4—C13—C14—C15179.4 (4)
C3—C4—C5—C61.3 (6)C12—C13—C14—C152.4 (6)
C2—C1—C6—C50.1 (6)C11—C10—C15—C140.5 (6)
Br2—C1—C6—C5179.6 (3)Br1—C10—C15—C14179.4 (3)
Br2—C1—C6—C5179.6 (3)Br1—C10—C15—C14179.4 (3)
C2—C1—C6—C9179.2 (4)C11—C10—C15—C18179.7 (4)
Br2—C1—C6—C91.1 (6)Br1—C10—C15—C181.4 (5)
Br2—C1—C6—C91.1 (6)Br1—C10—C15—C181.4 (5)
C4—C5—C6—C10.5 (6)C13—C14—C15—C101.6 (6)
C4—C5—C6—C9179.8 (4)C13—C14—C15—C18179.2 (4)
O3—N1—C9—C6180.0 (3)O6—N2—C18—C15179.0 (3)
C1—C6—C9—N1176.6 (4)C10—C15—C18—N2174.1 (4)
C5—C6—C9—N14.1 (6)C14—C15—C18—N26.8 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3A···O4i0.842.363.098 (5)147
O3—H3A···O5i0.842.032.747 (5)142
O6—H6A···O1ii0.842.192.942 (4)150
O6—H6A···O2ii0.842.333.038 (4)142
Symmetry codes: (i) x1, y+1/2, z+1/2; (ii) x, y1/2, z+1/2.
 

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