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Crystals of the title compound, C7H4BrNO, are twinned by a twofold rotation about [001]. The crystal structure is stabilized by π-stacking of the virtually planar fused ring system along the crystallographic a axis, and through weak inter­molecular C—H...O, C—H...N and C—H...Br inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807017278/pr2002sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807017278/pr2002Isup2.hkl
Contains datablock I

CCDC reference: 647297

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • R factor = 0.027
  • wR factor = 0.077
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B Crystal system given = monoclinic PLAT111_ALERT_2_B ADDSYM Detects (Pseudo) Centre of Symmetry ..... 80 PerFi PLAT112_ALERT_2_B ADDSYM Detects Additional (Pseudo) Symm. Elem... m PLAT480_ALERT_4_B Long H...A H-Bond Reported H12 .. BR1 .. 3.37 Ang.
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.430 From the CIF: _refine_ls_abs_structure_Flack_su 0.030 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.43 PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 1 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 11 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. N1 .. 3.38 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. BR1 .. 3.17 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H15 .. BR1 .. 3.10 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. N1 .. 2.85 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 .. N1 .. 2.71 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C7 H4 Br N O
Alert level G 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 27.17 From the CIF: _reflns_number_total 1428 Count of symmetry unique reflns 767 Completeness (_total/calc) 186.18% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 661 Fraction of Friedel pairs measured 0.862 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 9 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: COLLECT (Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

5-Bromoanthranil top
Crystal data top
C7H4BrNOF(000) = 192
Mr = 198.02Dx = 2.006 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 3.8265 (2) ÅCell parameters from 759 reflections
b = 9.6148 (6) Åθ = 2–27.0°
c = 8.9964 (5) ŵ = 6.18 mm1
β = 97.948 (4)°T = 100 K
V = 327.81 (3) Å3Needle, colourless
Z = 20.5 × 0.05 × 0.05 mm
Data collection top
Enraf–Nonius KappaCCD
diffractometer
1428 independent reflections
Radiation source: Enraf–Nonius FR5901341 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 9 pixels mm-1θmax = 27.2°, θmin = 2.3°
CCD rotation images, thick slices scansh = 44
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004; Blessing, 1995)
k = 1212
Tmin = 0.335, Tmax = 0.734l = 1111
4797 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.077 w = 1/[σ2(Fo2) + (0.0267P)2 + 0.9024P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max < 0.001
1428 reflectionsΔρmax = 0.72 e Å3
96 parametersΔρmin = 0.54 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.43 (3)
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 > 2σ(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
Br10.44854 (8)0.49338 (13)0.13265 (3)0.01714 (11)
O10.3479 (8)0.3514 (3)0.5159 (3)0.0217 (7)
N10.3408 (8)0.4967 (9)0.4895 (3)0.0190 (6)
C100.2150 (8)0.4917 (11)0.0681 (3)0.0142 (6)
C110.111 (2)0.6253 (8)0.1338 (7)0.0157 (16)
H110.17590.70800.07900.019*
C120.078 (2)0.6341 (7)0.2730 (9)0.0174 (13)
H120.15390.72110.31590.021*
C130.1594 (10)0.5045 (12)0.3530 (4)0.0204 (11)
C140.0442 (19)0.3776 (6)0.2887 (8)0.0154 (15)
C150.147 (2)0.3704 (8)0.1408 (8)0.0164 (15)
H150.22280.28410.09600.020*
C160.1740 (13)0.2835 (5)0.3965 (5)0.0209 (9)
H160.151 (12)0.182 (5)0.405 (5)0.017 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01588 (17)0.02112 (17)0.01345 (15)0.0000 (4)0.00143 (11)0.0004 (5)
O10.0267 (18)0.0208 (15)0.0169 (15)0.0012 (13)0.0003 (13)0.0036 (12)
N10.0227 (15)0.0163 (14)0.0173 (13)0.001 (4)0.0002 (10)0.002 (4)
C100.0104 (14)0.0185 (15)0.0138 (14)0.003 (4)0.0017 (11)0.007 (5)
C110.017 (3)0.010 (3)0.020 (3)0.001 (2)0.001 (3)0.001 (2)
C120.015 (3)0.014 (2)0.024 (3)0.001 (2)0.006 (2)0.003 (2)
C130.0170 (17)0.031 (3)0.0138 (15)0.001 (3)0.0052 (13)0.006 (3)
C140.011 (3)0.022 (3)0.012 (3)0.000 (2)0.000 (2)0.004 (2)
C150.018 (3)0.019 (4)0.012 (3)0.003 (3)0.002 (2)0.004 (2)
C160.028 (3)0.019 (2)0.016 (2)0.0030 (18)0.0042 (18)0.0007 (16)
Geometric parameters (Å, º) top
Br1—C101.901 (3)C12—C131.451 (13)
O1—C161.351 (6)C12—H120.9500
O1—N11.417 (9)C13—C141.395 (13)
N1—C131.326 (5)C14—C161.368 (8)
C10—C151.345 (12)C14—C151.429 (10)
C10—C111.447 (12)C15—H150.9500
C11—C121.360 (10)C16—H160.98 (5)
C11—H110.9500
C16—O1—N1110.3 (3)N1—C13—C12123.8 (9)
C13—N1—O1101.9 (7)C14—C13—C12120.8 (3)
C15—C10—C11123.2 (3)C16—C14—C13102.8 (6)
C15—C10—Br1120.2 (6)C16—C14—C15135.8 (7)
C11—C10—Br1116.6 (6)C13—C14—C15121.4 (7)
C12—C11—C10120.8 (7)C10—C15—C14116.8 (7)
C12—C11—H11119.6C10—C15—H15121.6
C10—C11—H11119.6C14—C15—H15121.6
C11—C12—C13117.0 (7)O1—C16—C14109.5 (4)
C11—C12—H12121.5O1—C16—H16117 (3)
C13—C12—H12121.5C14—C16—H16133 (3)
N1—C13—C14115.5 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···Br1i0.953.173.919 (8)138
C12—H12···Br1ii0.953.374.004 (7)126
C12—H12···O1iii0.952.593.412 (8)145
C15—H15···Br1iv0.953.103.938 (8)148
C16—H16···N1v0.98 (5)2.85 (5)3.618 (8)136 (3)
C16—H16···N1vi0.98 (5)2.71 (5)3.402 (8)128 (4)
Symmetry codes: (i) x1, y+1/2, z; (ii) x, y+1/2, z; (iii) x+1, y+1/2, z+1; (iv) x1, y1/2, z; (v) x, y1/2, z+1; (vi) x+1, y1/2, z+1.
 

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