(1RS,2SR)-1,2,4,5,7-Penta­bromo-5-methoxy­indane

In the title compound, C₁₀H₇Br₅O, prepared by bromination of 5-methoxy­indane, all bond lengths and angles are in the usual ranges. However, the relatively wide range of Br-C-C angles [107.2 (5)-117.0 (4)°] in the five-membered ring may indicate repulsion between the neighbouring Br atoms. The crystal packing is stabilized by van der Waals interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.041
• wR factor = 0.073
• Data-to-parameter ratio = 24.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.94

Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           29.55
           From the CIF: _diffrn_reflns_theta_full           0.00
           From the CIF: _reflns_number_total               3563
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         3777
           Completeness (_total/calc)             94.33%
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br3    ..  Br4     ..       3.56 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(1RS,2SR)-1,2,4,5,7-Pentabromo-5-methoxyindane

Crystal data

C10H7Br5O	Z = 2
Mr = 542.66	F(000) = 500
Triclinic, P1	Dx = 2.682 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.8895 (11) Å	Cell parameters from 7984 reflections
b = 8.9281 (10) Å	θ = 2.4–29.5°
c = 9.6787 (13) Å	µ = 14.93 mm^−1
α = 98.382 (10)°	T = 293 K
β = 113.16 (1)°	Prism, colorless
γ = 101.060 (9)°	0.55 × 0.41 × 0.26 mm
V = 671.99 (16) Å^3

Data collection

Stoe IPDS-II diffractometer	3563 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1562 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.167
Detector resolution: 6.67 pixels mm^-1	θmax = 29.6°, θmin = 2.4°
ω scans	h = −12→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.045, Tmax = 0.112	l = −13→13
13393 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.074	w = 1/[σ^2(Fo^2) + (0.0213P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.81	(Δ/σ)max < 0.001
3563 reflections	Δρmax = 0.49 e Å^−3
146 parameters	Δρmin = −0.67 e Å^−3
0 restraints	Extinction correction: SHELXL97, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0076 (5)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.05564 (9)	−0.38956 (7)	0.70585 (10)	0.0540 (3)
Br2	0.48174 (10)	−0.24854 (9)	0.93215 (10)	0.0616 (3)
Br3	0.77520 (9)	−0.15008 (8)	0.73156 (10)	0.0546 (3)
Br4	0.64356 (9)	0.43723 (8)	0.69282 (11)	0.0603 (3)
Br5	0.25845 (9)	0.29516 (8)	0.67368 (9)	0.0525 (3)
O1	0.8384 (5)	0.1947 (5)	0.7215 (6)	0.0494 (16)
C1	0.3545 (8)	0.0127 (7)	0.6895 (8)	0.0418 (19)
C2	0.1932 (8)	−0.0738 (7)	0.6881 (10)	0.050 (3)
C3	0.1973 (8)	−0.2469 (6)	0.6457 (8)	0.043 (2)
C4	0.3860 (7)	−0.2412 (7)	0.7115 (8)	0.043 (2)
C5	0.4666 (8)	−0.0819 (7)	0.7046 (8)	0.041 (2)
C6	0.6250 (8)	−0.0227 (7)	0.7149 (8)	0.0427 (19)
C7	0.6799 (7)	0.1324 (7)	0.7106 (8)	0.0401 (19)
C8	0.5661 (7)	0.2256 (6)	0.6950 (8)	0.043 (2)
C9	0.4079 (8)	0.1684 (7)	0.6862 (8)	0.045 (2)
C10	0.9656 (9)	0.2549 (10)	0.8803 (10)	0.066 (3)
H2A	0.09510	−0.05340	0.61070	0.0600*
H2B	0.19300	−0.04700	0.78890	0.0600*
H3	0.15150	−0.27910	0.53250	0.0520*
H4	0.40640	−0.32390	0.64820	0.0520*
H10A	1.07460	0.29540	0.88210	0.0990*
H10B	0.97000	0.17150	0.93310	0.0990*
H10C	0.93660	0.33760	0.93130	0.0990*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0565 (4)	0.0372 (4)	0.0754 (6)	0.0098 (3)	0.0356 (4)	0.0184 (4)
Br2	0.0694 (5)	0.0547 (4)	0.0508 (5)	0.0105 (4)	0.0158 (4)	0.0224 (4)
Br3	0.0496 (4)	0.0418 (4)	0.0786 (6)	0.0219 (3)	0.0282 (4)	0.0192 (4)
Br4	0.0586 (4)	0.0360 (4)	0.0943 (6)	0.0128 (3)	0.0370 (4)	0.0285 (4)
Br5	0.0521 (4)	0.0407 (3)	0.0716 (6)	0.0224 (3)	0.0274 (4)	0.0192 (3)
O1	0.040 (2)	0.050 (3)	0.058 (3)	0.009 (2)	0.021 (2)	0.018 (2)
C1	0.038 (3)	0.031 (3)	0.047 (4)	0.009 (3)	0.010 (3)	0.007 (3)
C2	0.038 (4)	0.034 (3)	0.082 (6)	0.011 (3)	0.027 (4)	0.020 (3)
C3	0.050 (4)	0.023 (3)	0.046 (4)	0.009 (3)	0.012 (3)	0.005 (3)
C4	0.040 (4)	0.032 (3)	0.047 (4)	0.006 (3)	0.013 (3)	0.001 (3)
C5	0.043 (4)	0.033 (3)	0.048 (4)	0.011 (3)	0.019 (3)	0.012 (3)
C6	0.038 (3)	0.035 (3)	0.044 (4)	0.010 (3)	0.007 (3)	0.009 (3)
C7	0.034 (3)	0.039 (3)	0.045 (4)	0.010 (3)	0.014 (3)	0.013 (3)
C8	0.040 (3)	0.027 (3)	0.060 (5)	0.008 (3)	0.017 (3)	0.021 (3)
C9	0.042 (4)	0.044 (3)	0.043 (4)	0.015 (3)	0.011 (3)	0.013 (3)
C10	0.041 (4)	0.082 (6)	0.053 (5)	0.002 (4)	0.007 (4)	0.010 (4)

Geometric parameters (Å, º)

Br1—C3	1.930 (7)	C4—C5	1.488 (9)
Br2—C4	1.980 (7)	C5—C6	1.364 (11)
Br3—C6	1.889 (7)	C6—C7	1.390 (9)
Br4—C8	1.889 (6)	C7—C8	1.406 (9)
Br5—C9	1.884 (7)	C8—C9	1.365 (10)
O1—C7	1.368 (9)	C2—H2A	0.9700
O1—C10	1.445 (10)	C2—H2B	0.9700
C1—C2	1.486 (11)	C3—H3	0.9800
C1—C5	1.404 (10)	C4—H4	0.9800
C1—C9	1.389 (9)	C10—H10A	0.9600
C2—C3	1.551 (9)	C10—H10B	0.9600
C3—C4	1.530 (10)	C10—H10C	0.9600
Br1···Br2	3.4015 (14)	Br3···H4	3.0700
Br1···Br3^i	3.6368 (13)	Br4···H4^vii	3.1300
Br1···Br4^ii	3.6377 (13)	Br4···H10C	3.1100
Br1···Br5^iii	3.6611 (12)	Br4···H4^viii	3.2300
Br1···Br1^iv	3.8217 (13)	Br5···H10A^i	3.0600
Br2···Br5^v	3.7367 (13)	Br5···H2A	3.0300
Br2···Br1	3.4015 (14)	O1···Br3	3.044 (5)
Br2···Br3	3.8664 (14)	O1···Br4	3.000 (5)
Br2···C1^v	3.514 (7)	O1···H3^vii	2.7000
Br2···C9^v	3.351 (7)	C1···Br2^v	3.514 (7)
Br3···Br2	3.8664 (14)	C9···Br3^vii	3.682 (7)
Br3···Br1^vi	3.6368 (13)	C9···Br2^v	3.351 (7)
Br3···C9^vii	3.682 (7)	C10···Br3	3.497 (9)
Br3···Br4^iii	3.5614 (12)	C10···Br4	3.564 (9)
Br3···O1	3.044 (5)	C6···H10B	2.9400
Br3···C10	3.497 (9)	C8···H10C	3.0400
Br3···Br5^vii	3.8208 (13)	H2A···Br5	3.0300
Br4···Br5	3.3361 (13)	H2A···H2A^xi	2.5900
Br4···O1	3.000 (5)	H3···Br1^iv	3.1700
Br4···Br3^viii	3.5614 (12)	H3···O1^vii	2.7000
Br4···Br1^ix	3.6377 (13)	H4···Br3	3.0700
Br4···C10	3.564 (9)	H4···Br4^iii	3.2300
Br5···Br3^vii	3.8208 (13)	H4···Br4^vii	3.1300
Br5···Br4	3.3361 (13)	H10A···Br5^vi	3.0600
Br5···Br2^v	3.7367 (13)	H10B···Br3	2.9700
Br5···Br1^viii	3.6611 (12)	H10B···C6	2.9400
Br1···H3^iv	3.1700	H10B···Br3^x	3.2000
Br3···H10B	2.9700	H10C···Br4	3.1100
Br3···H10B^x	3.2000	H10C···C8	3.0400
C7—O1—C10	112.5 (6)	C7—C8—C9	122.0 (6)
C2—C1—C5	111.4 (6)	Br5—C9—C1	118.1 (6)
C2—C1—C9	129.6 (7)	Br5—C9—C8	122.2 (5)
C5—C1—C9	118.9 (7)	C1—C9—C8	119.7 (7)
C1—C2—C3	101.2 (6)	C1—C2—H2A	112.00
Br1—C3—C2	112.9 (5)	C1—C2—H2B	112.00
Br1—C3—C4	117.0 (4)	C3—C2—H2A	112.00
C2—C3—C4	105.3 (5)	C3—C2—H2B	112.00
Br2—C4—C3	112.6 (5)	H2A—C2—H2B	109.00
Br2—C4—C5	107.2 (5)	Br1—C3—H3	107.00
C3—C4—C5	102.7 (5)	C2—C3—H3	107.00
C1—C5—C4	109.8 (6)	C4—C3—H3	107.00
C1—C5—C6	120.8 (6)	Br2—C4—H4	111.00
C4—C5—C6	129.5 (6)	C3—C4—H4	111.00
Br3—C6—C5	121.1 (5)	C5—C4—H4	111.00
Br3—C6—C7	117.9 (6)	O1—C10—H10A	109.00
C5—C6—C7	121.1 (7)	O1—C10—H10B	109.00
O1—C7—C6	122.2 (6)	O1—C10—H10C	109.00
O1—C7—C8	120.3 (6)	H10A—C10—H10B	109.00
C6—C7—C8	117.5 (6)	H10A—C10—H10C	110.00
Br4—C8—C7	117.2 (5)	H10B—C10—H10C	109.00
Br4—C8—C9	120.8 (5)
C10—O1—C7—C8	93.8 (8)	Br2—C4—C5—C1	−100.8 (6)
C10—O1—C7—C6	−85.9 (8)	C3—C4—C5—C6	−163.8 (7)
C9—C1—C2—C3	164.3 (7)	C3—C4—C5—C1	18.1 (7)
C2—C1—C5—C4	1.1 (8)	C1—C5—C6—Br3	−178.9 (5)
C5—C1—C2—C3	−19.4 (8)	C4—C5—C6—C7	−178.0 (7)
C5—C1—C9—Br5	−177.7 (5)	C1—C5—C6—C7	−0.1 (11)
C5—C1—C9—C8	1.1 (10)	C4—C5—C6—Br3	3.2 (11)
C2—C1—C5—C6	−177.2 (7)	Br3—C6—C7—O1	−1.5 (9)
C9—C1—C5—C4	177.9 (6)	C5—C6—C7—C8	−0.1 (10)
C9—C1—C5—C6	−0.4 (10)	Br3—C6—C7—C8	178.7 (5)
C2—C1—C9—Br5	−1.5 (11)	C5—C6—C7—O1	179.7 (6)
C2—C1—C9—C8	177.2 (7)	O1—C7—C8—Br4	−0.8 (9)
C1—C2—C3—Br1	158.5 (5)	O1—C7—C8—C9	−179.0 (6)
C1—C2—C3—C4	29.8 (7)	C6—C7—C8—Br4	179.0 (5)
Br1—C3—C4—Br2	−40.8 (6)	C6—C7—C8—C9	0.8 (10)
C2—C3—C4—C5	−29.6 (7)	C7—C8—C9—C1	−1.3 (11)
C2—C3—C4—Br2	85.4 (6)	Br4—C8—C9—Br5	−0.7 (8)
Br1—C3—C4—C5	−155.8 (5)	Br4—C8—C9—C1	−179.4 (5)
Br2—C4—C5—C6	77.3 (8)	C7—C8—C9—Br5	177.4 (5)

Symmetry codes: (i) x−1, y, z; (ii) x−1, y−1, z; (iii) x, y−1, z; (iv) −x, −y−1, −z+1; (v) −x+1, −y, −z+2; (vi) x+1, y, z; (vii) −x+1, −y, −z+1; (viii) x, y+1, z; (ix) x+1, y+1, z; (x) −x+2, −y, −z+2; (xi) −x, −y, −z+1.