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The title compound, C13H15BrINO, contains two mol­ecules in the asymmetric unit which are linked into dimeric associations by way of very short C—I...O inter­actions [I...O = 2.998 (4) and 3.044 (4) Å]. The cyclo­pentane rings of both mol­ecules are disordered; the site occupancy ratios are ca 0.54:0.46 and 0.59:0.41.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032370/bt2427sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032370/bt2427Isup2.hkl
Contains datablock I

CCDC reference: 657691

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.007 Å
  • Disorder in main residue
  • R factor = 0.039
  • wR factor = 0.102
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.91
Author Response: this less than ideal situation seemed to arise from a glitch in the data collection software. However, we consider that this coverage is sufficient for the purposes of this study. Satisfactory precision on the derived geometrical parameters has been obtained.

PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       7.33 Ratio
Author Response: Arising from the disorder of the cyclopentane rings.
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       5.71 Ratio
Author Response: Arising from the disorder of the cyclopentane rings.
PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       6.87 Ratio
Author Response: Arising from the disorder of the cyclopentane rings (with H atoms riding on C atoms).

PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.46 Ratio
Author Response: Arising from the disorder of the cyclopentane rings (with H atoms riding on C atoms).


Alert level B PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 4 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C10 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C23 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C11A PLAT431_ALERT_2_B Short Inter HL..A Contact I1 .. O2 .. 3.04 Ang. PLAT431_ALERT_2_B Short Inter HL..A Contact I2 .. O1 .. 3.00 Ang.
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _diffrn_reflns_theta_full 26.00 From the CIF: _reflns_number_total 5099 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5585 Completeness (_total/calc) 91.30% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.91 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.95 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C12A PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C26 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24B PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24A PLAT301_ALERT_3_C Main Residue Disorder ......................... 11.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 27.60 Deg. C13 -C9 -C13A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 16.70 Deg. C11 -C10 -C11A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 33.20 Deg. C24B -C23 -C24A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 31.90 Deg. C24A -C25 -C24B 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C13 H15 Br I N O
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C22 = ... R
5 ALERT level A = In general: serious problem 6 ALERT level B = Potentially serious problem 15 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 18 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 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

Comment top

The title compound, (I), complements the recently reported cyclohexanecarboxylic acid (5-bromo-2-iodo-phenyl)-methyl-amide, (II), (Slawin et al., 2007), with a cyclopentane ring in (I) replacing a cyclohexane ring in (II).

There are two molecules in the asymmetric unit of (I) and their geometrical parameters fall within the expected ranges, allowing for the uncertainties arising from the disordered cyclopentane rings (Allen et al., 1995).

For the first (C1) molecule, the dihedral angle between the mean planes of the aromatic ring and the methylated amide (C7/C8/N1/O1) group is 85.4 (2)°. A dihedral angle of 82.35 (17)° occurs for the equivalent atoms in the second (C14) molecule. In both molecules the methyl C atom and the O atom of the amide are in cis conformation.

In the crystal, the molecules of (I) form dimers (Fig. 1) by way of two very short C—I···O interactions (Allen et al., 1997; Glidewell et al., 2005) with the iodine···oxygen separations for C1—I1···O2 and C14—I2···O1 being 3.044 (4)Å and 2.998 (4) Å, respectively. The Bondi (1964) van der Waals' separation for I and O is 3.50 Å. The C1—I1···O2 and C14—I2···O1 angles are 171.12 (14)° and 174.44 (14), respectively.

A dimerization of the two asymmetric molecules via two very short C—I···O interactions [I···O = 3.038 (4) and 3.082 (4) Å]. also occurs in (II) (Slawin et al., 2007).

Related literature top

For a related structure, see Slawin et al. (2007). For background on C—I···O interactions, see: Allen et al. (1997); Glidewell et al. (2005). For crystallographic reference data, see: Bondi (1964); Allen et al. (1995).

Experimental top

2-Iodo-5-bromoaniline (596 mg, 2.55 mmol) was added to DCM (5 ml) with triethylamine (0.7 ml, 5 mmol), and the mixture stirred magnetically whilst chilled in an ice bath. Once cool, cyclopentane carbonyl chloride (0.4 ml, 3 mmol) was added dropwise, and the mixture stirred for 2 hr during which time a precipitate was produced. Water (10 ml) was added to the flask, then the DCM layer was separated and washed with saturated sodium hydrogen carbonate (15 ml) and brine (15 ml), during which time the mixture emulsified. The DCM layer was filtered to yield a pure white filtrate and a yellow liquor which was dried (MgSO4), and the solvent removed to yield colourless plates of cyclopentanecarboxylic acid (5-bromo-2-iodo-phenyl)-amide, (III).

Compound (III) (750 mg, 1.8 mmol) was dissolved in dry THF (10 ml), then injected into a pre-dried flask containing sodium hydride (40 mg, 1.8 mmol) in dry THF (10 ml) and the mixture stirred magnetically. When bubbling of the mixture ceased, methyl iodide (0.12 ml, 1.98 mmol) was added and the reaction left stirring overnight. Ammonium carbonate solution (10 ml) was then added and the mixture allowed to stir for 10 min, during which time a white precipitate formed which redissolved on the addition of water (15 ml). An extraction was performed into ethyl acetate (3 × 20 ml). Purification by flash column chromatography (10:1 v/v hexane:ethyl acetate) yielded 385 mg (51%) of the title compound with Rf = 0.20. Recrystallization from ethyl acetate afforded colourless prisms of (I).

Refinement top

The disordered atoms were refined isotropically. The hydrogen atoms were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The highest difference peak is 1.20Å from H25A and the deepest difference hole is 0.84Å from I1.

Structure description top

The title compound, (I), complements the recently reported cyclohexanecarboxylic acid (5-bromo-2-iodo-phenyl)-methyl-amide, (II), (Slawin et al., 2007), with a cyclopentane ring in (I) replacing a cyclohexane ring in (II).

There are two molecules in the asymmetric unit of (I) and their geometrical parameters fall within the expected ranges, allowing for the uncertainties arising from the disordered cyclopentane rings (Allen et al., 1995).

For the first (C1) molecule, the dihedral angle between the mean planes of the aromatic ring and the methylated amide (C7/C8/N1/O1) group is 85.4 (2)°. A dihedral angle of 82.35 (17)° occurs for the equivalent atoms in the second (C14) molecule. In both molecules the methyl C atom and the O atom of the amide are in cis conformation.

In the crystal, the molecules of (I) form dimers (Fig. 1) by way of two very short C—I···O interactions (Allen et al., 1997; Glidewell et al., 2005) with the iodine···oxygen separations for C1—I1···O2 and C14—I2···O1 being 3.044 (4)Å and 2.998 (4) Å, respectively. The Bondi (1964) van der Waals' separation for I and O is 3.50 Å. The C1—I1···O2 and C14—I2···O1 angles are 171.12 (14)° and 174.44 (14), respectively.

A dimerization of the two asymmetric molecules via two very short C—I···O interactions [I···O = 3.038 (4) and 3.082 (4) Å]. also occurs in (II) (Slawin et al., 2007).

For a related structure, see Slawin et al. (2007). For background on C—I···O interactions, see: Allen et al. (1997); Glidewell et al. (2005). For crystallographic reference data, see: Bondi (1964); Allen et al. (1995).

Computing details top

Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I) showing 50% displacement ellipsoids (H atoms omitted for clarity) showing the C—I···O interactions as double dashed lines. Only one disorder component of each cyclopentane ring is shown.
N-(5-Bromo-2-iodophenyl)-N-methylcyclopentanecarboxamide top
Crystal data top
C13H15BrINOV = 1423.6 (4) Å3
Mr = 408.07Z = 4
Triclinic, P1F(000) = 784
Hall symbol: -P 1Dx = 1.904 Mg m3
a = 9.0116 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.8073 (18) ŵ = 5.04 mm1
c = 13.697 (2) ÅT = 93 K
α = 86.430 (12)°Block, colourless
β = 85.395 (13)°0.30 × 0.20 × 0.10 mm
γ = 78.849 (11)°
Data collection top
Rigaku Mercury CCD
diffractometer
5099 independent reflections
Radiation source: rotating anode4616 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.033
ω and φ scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2004)
h = 911
Tmin = 0.313, Tmax = 0.633k = 1414
9341 measured reflectionsl = 1316
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0565P)2 + 4.5633P]
where P = (Fo2 + 2Fc2)/3
5099 reflections(Δ/σ)max = 0.002
305 parametersΔρmax = 1.28 e Å3
0 restraintsΔρmin = 1.51 e Å3
Crystal data top
C13H15BrINOγ = 78.849 (11)°
Mr = 408.07V = 1423.6 (4) Å3
Triclinic, P1Z = 4
a = 9.0116 (14) ÅMo Kα radiation
b = 11.8073 (18) ŵ = 5.04 mm1
c = 13.697 (2) ÅT = 93 K
α = 86.430 (12)°0.30 × 0.20 × 0.10 mm
β = 85.395 (13)°
Data collection top
Rigaku Mercury CCD
diffractometer
5099 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2004)
4616 reflections with I > 2σ(I)
Tmin = 0.313, Tmax = 0.633Rint = 0.033
9341 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.02Δρmax = 1.28 e Å3
5099 reflectionsΔρmin = 1.51 e Å3
305 parameters
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*/UeqOcc. (<1)
C11.1153 (5)0.1887 (4)0.2547 (3)0.0124 (9)
C21.2706 (5)0.2157 (4)0.2354 (4)0.0161 (10)
H21.33100.16060.24620.019*
C31.3396 (5)0.3226 (4)0.2003 (3)0.0160 (10)
H31.44630.34080.18680.019*
C41.2494 (5)0.4020 (4)0.1854 (3)0.0132 (9)
C51.0937 (5)0.3760 (4)0.2046 (3)0.0121 (9)
H51.03380.43170.19450.015*
C61.0248 (5)0.2686 (4)0.2387 (3)0.0115 (9)
C70.8129 (6)0.2720 (5)0.3635 (4)0.0272 (12)
H7A0.90100.29760.40230.041*
H7B0.75360.33350.36500.041*
H7C0.74970.20270.39100.041*
C80.7602 (5)0.2074 (4)0.1952 (4)0.0161 (10)
C90.8155 (6)0.1777 (5)0.0919 (4)0.0285 (12)
H90.92860.19130.09130.034*
C100.7655 (14)0.0507 (6)0.0590 (6)0.086 (4)
H10A0.65690.02460.07930.103*
H10B0.82460.00260.09080.103*
C110.787 (2)0.0374 (16)0.0402 (13)0.058 (5)*0.54 (2)
H11A0.88880.01900.05890.069*0.54 (2)
H11B0.70940.02560.06630.069*0.54 (2)
C120.773 (2)0.1645 (12)0.0832 (10)0.042 (4)*0.54 (2)
H12A0.67620.15930.11380.051*0.54 (2)
H12B0.85830.19150.13170.051*0.54 (2)
C130.7807 (15)0.2456 (8)0.0118 (7)0.018 (3)*0.54 (2)
H13A0.68250.27060.02770.022*0.54 (2)
H13B0.86080.31510.00250.022*0.54 (2)
C11A0.748 (2)0.0505 (15)0.0543 (13)0.042 (4)*0.46 (2)
H11C0.67140.01650.07590.051*0.46 (2)
H11D0.84560.04820.09220.051*0.46 (2)
C12A0.704 (3)0.1467 (18)0.0650 (16)0.063 (6)*0.46 (2)
H12C0.77230.19100.11520.075*0.46 (2)
H12D0.60050.12960.08880.075*0.46 (2)
C13A0.702 (3)0.2148 (16)0.0228 (12)0.045 (5)*0.46 (2)
H13C0.73400.29770.00900.054*0.46 (2)
H13D0.59840.20300.05520.054*0.46 (2)
N10.8644 (4)0.2453 (3)0.2616 (3)0.0134 (8)
O10.6240 (4)0.1954 (3)0.2193 (3)0.0228 (8)
Br11.33872 (5)0.54869 (4)0.13779 (3)0.01845 (13)
I11.01734 (3)0.02584 (2)0.30608 (2)0.01834 (11)
C140.4091 (5)0.1964 (4)0.3579 (3)0.0116 (9)
C150.2554 (5)0.2366 (4)0.3541 (3)0.0132 (9)
H150.19420.18920.32960.016*
C160.1887 (5)0.3460 (4)0.3858 (3)0.0148 (9)
H160.08260.37340.38370.018*
C170.2814 (5)0.4141 (4)0.4205 (3)0.0105 (9)
C180.4349 (5)0.3751 (4)0.4247 (3)0.0111 (9)
H180.49590.42270.44910.013*
C190.5009 (5)0.2656 (4)0.3930 (3)0.0115 (9)
C200.7014 (6)0.1548 (4)0.4922 (4)0.0197 (10)
H20A0.60940.13980.52980.030*
H20B0.75640.19660.53210.030*
H20C0.76610.08130.47450.030*
C210.7703 (5)0.2563 (4)0.3387 (3)0.0137 (9)
C220.7215 (5)0.3257 (4)0.2463 (4)0.0177 (10)
H220.61250.36390.25570.021*
C230.8186 (10)0.4167 (6)0.2159 (5)0.059 (2)
H23A0.75820.49580.22210.071*
H23B0.90650.40740.25660.071*
C24A0.870 (2)0.3936 (16)0.1089 (11)0.038 (5)*0.41 (2)
H24A0.86560.46770.07010.045*0.41 (2)
H24B0.97660.35100.10410.045*0.41 (2)
C24B0.7931 (14)0.4481 (10)0.1136 (7)0.031 (3)*0.59 (2)
H24C0.88060.47690.07950.038*0.59 (2)
H24D0.70030.50770.10700.038*0.59 (2)
C250.7743 (9)0.3274 (7)0.0718 (5)0.0525 (18)
H25A0.82590.28160.01640.063*
H25B0.67970.37680.05030.063*
C260.7441 (10)0.2519 (6)0.1590 (4)0.055 (2)
H26A0.83080.18710.16670.066*
H26B0.65220.21970.15190.066*
N20.6596 (4)0.2249 (3)0.4027 (3)0.0113 (8)
O20.9042 (4)0.2256 (3)0.3547 (3)0.0205 (7)
Br20.19457 (5)0.56264 (4)0.46655 (3)0.01497 (13)
I20.50529 (3)0.03337 (2)0.30769 (2)0.01627 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.011 (2)0.0097 (19)0.015 (2)0.0024 (17)0.0031 (18)0.0017 (17)
C20.012 (2)0.016 (2)0.021 (2)0.0048 (19)0.0006 (19)0.0012 (19)
C30.010 (2)0.019 (2)0.019 (2)0.0029 (19)0.0014 (19)0.0002 (19)
C40.015 (2)0.012 (2)0.012 (2)0.0010 (18)0.0008 (18)0.0021 (17)
C50.010 (2)0.015 (2)0.012 (2)0.0055 (18)0.0017 (18)0.0001 (17)
C60.010 (2)0.016 (2)0.008 (2)0.0016 (17)0.0004 (17)0.0027 (17)
C70.021 (3)0.035 (3)0.020 (3)0.003 (2)0.006 (2)0.012 (2)
C80.011 (3)0.016 (2)0.022 (2)0.0010 (18)0.006 (2)0.0051 (19)
C90.017 (3)0.050 (3)0.014 (2)0.007 (2)0.004 (2)0.006 (2)
C100.183 (11)0.039 (4)0.042 (4)0.056 (6)0.039 (6)0.013 (3)
N10.0090 (19)0.0192 (19)0.0115 (19)0.0042 (15)0.0019 (15)0.0050 (15)
O10.0085 (18)0.0267 (18)0.034 (2)0.0042 (14)0.0009 (15)0.0075 (16)
Br10.0197 (3)0.0146 (2)0.0195 (3)0.00165 (19)0.0020 (2)0.00340 (18)
I10.01572 (19)0.01515 (17)0.02395 (19)0.00073 (13)0.00382 (13)0.00309 (12)
C140.011 (2)0.012 (2)0.011 (2)0.0020 (17)0.0024 (18)0.0001 (17)
C150.011 (2)0.016 (2)0.014 (2)0.0075 (18)0.0018 (18)0.0025 (18)
C160.008 (2)0.024 (2)0.013 (2)0.0030 (18)0.0013 (18)0.0006 (18)
C170.010 (2)0.014 (2)0.006 (2)0.0004 (17)0.0021 (17)0.0011 (16)
C180.009 (2)0.015 (2)0.010 (2)0.0051 (18)0.0003 (17)0.0005 (17)
C190.011 (2)0.016 (2)0.008 (2)0.0048 (18)0.0004 (17)0.0015 (17)
C200.020 (3)0.023 (2)0.017 (2)0.005 (2)0.008 (2)0.006 (2)
C210.009 (2)0.014 (2)0.019 (2)0.0034 (18)0.0004 (19)0.0053 (18)
C220.012 (2)0.021 (2)0.019 (2)0.0021 (19)0.0021 (19)0.0022 (19)
C230.097 (6)0.047 (4)0.051 (4)0.051 (4)0.024 (4)0.012 (3)
C250.061 (5)0.063 (5)0.029 (4)0.007 (4)0.007 (3)0.001 (3)
C260.106 (6)0.033 (3)0.022 (3)0.004 (4)0.019 (4)0.003 (3)
N20.0058 (19)0.0151 (18)0.0124 (18)0.0011 (15)0.0011 (15)0.0016 (15)
O20.0095 (17)0.0194 (17)0.033 (2)0.0031 (13)0.0052 (15)0.0016 (15)
Br20.0117 (3)0.0145 (2)0.0182 (2)0.00015 (18)0.00163 (19)0.00392 (18)
I20.01425 (19)0.01533 (16)0.02016 (18)0.00486 (12)0.00063 (13)0.00245 (12)
Geometric parameters (Å, º) top
C1—C21.382 (7)C12A—H12D0.9900
C1—C61.398 (6)C13A—H13C0.9900
C1—I12.093 (4)C13A—H13D0.9900
C2—C31.391 (7)C14—C151.379 (6)
C2—H20.9500C14—C191.399 (6)
C3—C41.388 (6)C14—I22.086 (4)
C3—H30.9500C15—C161.395 (6)
C4—C51.384 (7)C15—H150.9500
C4—Br11.895 (4)C16—C171.394 (6)
C5—C61.391 (6)C16—H160.9500
C5—H50.9500C17—C181.375 (6)
C6—N11.431 (6)C17—Br21.901 (4)
C7—N11.470 (6)C18—C191.394 (6)
C7—H7A0.9800C18—H180.9500
C7—H7B0.9800C19—N21.432 (6)
C7—H7C0.9800C20—N21.469 (6)
C8—O11.228 (6)C20—H20A0.9800
C8—N11.353 (6)C20—H20B0.9800
C8—C91.506 (7)C20—H20C0.9800
C9—C131.486 (10)C21—O21.225 (6)
C9—C101.530 (10)C21—N21.365 (6)
C9—C13A1.586 (17)C21—C221.512 (6)
C9—H91.0000C22—C261.501 (8)
C10—C111.361 (19)C22—C231.531 (7)
C10—C11A1.57 (2)C22—H221.0000
C10—H10A0.9900C23—C24B1.451 (12)
C10—H10B0.9900C23—C24A1.527 (18)
C11—C121.68 (2)C23—H23A0.9900
C11—H11A0.9900C23—H23B0.9900
C11—H11B0.9900C24A—C251.415 (16)
C12—C131.565 (16)C24A—H24A0.9900
C12—H12A0.9900C24A—H24B0.9900
C12—H12B0.9900C24B—C251.612 (13)
C13—H13A0.9900C24B—H24C0.9900
C13—H13B0.9900C24B—H24D0.9900
C11A—C12A1.29 (3)C25—C261.485 (9)
C11A—H11C0.9900C25—H25A0.9900
C11A—H11D0.9900C25—H25B0.9900
C12A—C13A1.40 (2)C26—H26A0.9900
C12A—H12C0.9900C26—H26B0.9900
C2—C1—C6120.3 (4)C12A—C13A—H13D110.1
C2—C1—I1119.1 (3)C9—C13A—H13D110.1
C6—C1—I1120.6 (3)H13C—C13A—H13D108.4
C1—C2—C3120.8 (4)C8—N1—C6124.5 (4)
C1—C2—H2119.6C8—N1—C7119.2 (4)
C3—C2—H2119.6C6—N1—C7116.2 (4)
C4—C3—C2118.7 (4)C15—C14—C19120.2 (4)
C4—C3—H3120.6C15—C14—I2119.7 (3)
C2—C3—H3120.6C19—C14—I2120.1 (3)
C5—C4—C3121.1 (4)C14—C15—C16120.8 (4)
C5—C4—Br1118.8 (3)C14—C15—H15119.6
C3—C4—Br1120.1 (3)C16—C15—H15119.6
C4—C5—C6120.1 (4)C17—C16—C15118.4 (4)
C4—C5—H5120.0C17—C16—H16120.8
C6—C5—H5120.0C15—C16—H16120.8
C5—C6—C1119.0 (4)C18—C17—C16121.4 (4)
C5—C6—N1119.1 (4)C18—C17—Br2118.8 (3)
C1—C6—N1121.7 (4)C16—C17—Br2119.7 (3)
N1—C7—H7A109.5C17—C18—C19120.0 (4)
N1—C7—H7B109.5C17—C18—H18120.0
H7A—C7—H7B109.5C19—C18—H18120.0
N1—C7—H7C109.5C18—C19—C14119.2 (4)
H7A—C7—H7C109.5C18—C19—N2118.8 (4)
H7B—C7—H7C109.5C14—C19—N2121.9 (4)
O1—C8—N1120.8 (4)N2—C20—H20A109.5
O1—C8—C9120.9 (4)N2—C20—H20B109.5
N1—C8—C9118.3 (4)H20A—C20—H20B109.5
C13—C9—C8118.1 (6)N2—C20—H20C109.5
C13—C9—C10105.8 (6)H20A—C20—H20C109.5
C8—C9—C10114.2 (5)H20B—C20—H20C109.5
C13—C9—C13A27.6 (6)O2—C21—N2120.5 (4)
C8—C9—C13A106.1 (7)O2—C21—C22121.8 (4)
C10—C9—C13A90.8 (8)N2—C21—C22117.6 (4)
C13—C9—H9106.0C26—C22—C21111.8 (4)
C8—C9—H9106.0C26—C22—C23102.9 (5)
C10—C9—H9106.0C21—C22—C23112.6 (4)
C13A—C9—H9133.2C26—C22—H22109.8
C11—C10—C9110.0 (9)C21—C22—H22109.8
C11—C10—C11A16.7 (10)C23—C22—H22109.8
C9—C10—C11A105.5 (8)C24B—C23—C24A33.2 (7)
C11—C10—H10A109.7C24B—C23—C22105.7 (6)
C9—C10—H10A109.7C24A—C23—C22104.0 (7)
C11A—C10—H10A97.3C24B—C23—H23A80.0
C11—C10—H10B109.7C24A—C23—H23A110.9
C9—C10—H10B109.7C22—C23—H23A110.9
C11A—C10—H10B125.4C24B—C23—H23B135.2
H10A—C10—H10B108.2C24A—C23—H23B110.9
C10—C11—C12105.3 (12)C22—C23—H23B110.9
C10—C11—H11A110.7H23A—C23—H23B109.0
C12—C11—H11A110.7C25—C24A—C23108.7 (11)
C10—C11—H11B110.7C25—C24A—H24A110.0
C12—C11—H11B110.7C23—C24A—H24A110.0
H11A—C11—H11B108.8C25—C24A—H24B110.0
C13—C12—C11102.4 (10)C23—C24A—H24B110.0
C13—C12—H12A111.3H24A—C24A—H24B108.3
C11—C12—H12A111.3C23—C24B—C25102.5 (7)
C13—C12—H12B111.3C23—C24B—H24C111.3
C11—C12—H12B111.3C25—C24B—H24C111.3
H12A—C12—H12B109.2C23—C24B—H24D111.3
C9—C13—C12106.7 (7)C25—C24B—H24D111.3
C9—C13—H13A110.4H24C—C24B—H24D109.2
C12—C13—H13A110.4C24A—C25—C26101.4 (8)
C9—C13—H13B110.4C24A—C25—C24B31.9 (7)
C12—C13—H13B110.4C26—C25—C24B105.9 (6)
H13A—C13—H13B108.6C24A—C25—H25A111.5
C12A—C11A—C10103.7 (15)C26—C25—H25A111.5
C12A—C11A—H11C111.0C24B—C25—H25A133.1
C10—C11A—H11C111.0C24A—C25—H25B111.5
C12A—C11A—H11D111.0C26—C25—H25B111.5
C10—C11A—H11D111.0C24B—C25—H25B80.8
H11C—C11A—H11D109.0H25A—C25—H25B109.3
C11A—C12A—C13A112.4 (18)C25—C26—C22106.9 (5)
C11A—C12A—H12C109.1C25—C26—H26A110.3
C13A—C12A—H12C109.1C22—C26—H26A110.3
C11A—C12A—H12D109.1C25—C26—H26B110.3
C13A—C12A—H12D109.1C22—C26—H26B110.3
H12C—C12A—H12D107.9H26A—C26—H26B108.6
C12A—C13A—C9108.1 (13)C21—N2—C19123.6 (4)
C12A—C13A—H13C110.1C21—N2—C20119.8 (4)
C9—C13A—H13C110.1C19—N2—C20116.4 (3)
C6—C1—C2—C30.3 (7)C1—C6—N1—C898.8 (5)
I1—C1—C2—C3179.4 (3)C5—C6—N1—C791.4 (5)
C1—C2—C3—C40.3 (7)C1—C6—N1—C785.1 (5)
C2—C3—C4—C50.2 (7)C19—C14—C15—C160.5 (7)
C2—C3—C4—Br1179.9 (3)I2—C14—C15—C16179.0 (3)
C3—C4—C5—C60.5 (7)C14—C15—C16—C170.6 (7)
Br1—C4—C5—C6179.4 (3)C15—C16—C17—C180.6 (7)
C4—C5—C6—C11.1 (7)C15—C16—C17—Br2178.9 (3)
C4—C5—C6—N1177.7 (4)C16—C17—C18—C190.5 (6)
C2—C1—C6—C51.0 (7)Br2—C17—C18—C19178.8 (3)
I1—C1—C6—C5180.0 (3)C17—C18—C19—C140.4 (6)
C2—C1—C6—N1177.5 (4)C17—C18—C19—N2176.9 (4)
I1—C1—C6—N13.5 (6)C15—C14—C19—C180.4 (6)
O1—C8—C9—C1363.9 (8)I2—C14—C19—C18178.9 (3)
N1—C8—C9—C13117.6 (7)C15—C14—C19—N2176.8 (4)
O1—C8—C9—C1061.4 (8)I2—C14—C19—N24.6 (6)
N1—C8—C9—C10117.2 (7)O2—C21—C22—C2676.3 (6)
O1—C8—C9—C13A37.0 (10)N2—C21—C22—C26101.3 (6)
N1—C8—C9—C13A144.5 (9)O2—C21—C22—C2339.1 (7)
C13—C9—C10—C1133.6 (13)N2—C21—C22—C23143.3 (5)
C8—C9—C10—C11165.1 (12)C26—C22—C23—C24B41.2 (9)
C13A—C9—C10—C1157.1 (13)C21—C22—C23—C24B161.8 (7)
C13—C9—C10—C11A16.7 (11)C26—C22—C23—C24A6.8 (10)
C8—C9—C10—C11A148.2 (9)C21—C22—C23—C24A127.5 (9)
C13A—C9—C10—C11A40.2 (12)C24B—C23—C24A—C2578.8 (15)
C9—C10—C11—C1228.0 (16)C22—C23—C24A—C2518.5 (15)
C11A—C10—C11—C1249 (4)C24A—C23—C24B—C2556.7 (12)
C10—C11—C12—C1313.1 (16)C22—C23—C24B—C2535.1 (9)
C8—C9—C13—C12151.9 (8)C23—C24A—C25—C2635.9 (14)
C10—C9—C13—C1222.5 (10)C23—C24A—C25—C24B66.1 (14)
C13A—C9—C13—C1282.0 (16)C23—C24B—C25—C24A69.0 (14)
C11—C12—C13—C96.8 (13)C23—C24B—C25—C2616.9 (10)
C11—C10—C11A—C12A141 (5)C24A—C25—C26—C2240.7 (11)
C9—C10—C11A—C12A32.5 (18)C24B—C25—C26—C228.2 (9)
C10—C11A—C12A—C13A5 (2)C21—C22—C26—C25150.2 (5)
C11A—C12A—C13A—C923 (2)C23—C22—C26—C2529.0 (8)
C13—C9—C13A—C12A85.2 (19)O2—C21—N2—C19174.5 (4)
C8—C9—C13A—C12A154.3 (13)C22—C21—N2—C197.9 (6)
C10—C9—C13A—C12A38.8 (15)O2—C21—N2—C200.7 (6)
O1—C8—N1—C6175.9 (4)C22—C21—N2—C20178.4 (4)
C9—C8—N1—C65.6 (7)C18—C19—N2—C2180.3 (5)
O1—C8—N1—C70.1 (7)C14—C19—N2—C21103.3 (5)
C9—C8—N1—C7178.5 (4)C18—C19—N2—C2093.7 (5)
C5—C6—N1—C884.7 (6)C14—C19—N2—C2082.8 (5)

Experimental details

Crystal data
Chemical formulaC13H15BrINO
Mr408.07
Crystal system, space groupTriclinic, P1
Temperature (K)93
a, b, c (Å)9.0116 (14), 11.8073 (18), 13.697 (2)
α, β, γ (°)86.430 (12), 85.395 (13), 78.849 (11)
V3)1423.6 (4)
Z4
Radiation typeMo Kα
µ (mm1)5.04
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerRigaku Mercury CCD
Absorption correctionMulti-scan
(CrystalClear; Rigaku, 2004)
Tmin, Tmax0.313, 0.633
No. of measured, independent and
observed [I > 2σ(I)] reflections
9341, 5099, 4616
Rint0.033
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.102, 1.02
No. of reflections5099
No. of parameters305
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.28, 1.51

Computer programs: CrystalClear (Rigaku, 2004), CrystalClear, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

 

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