3-(2-Bromo­phenyl)isocoumarin

The mol­ecular structure of the title compound, C₁₅H₉BrO₂, consists of two essentially planar units, benzopyran-1-one and 2-bromo­phenyl, which are inclined at 51.42 (12)° with respect to one another. The structure is stabilized by two weak inter­molecular C—H...O inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.038
• wR factor = 0.094
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
STRVA01_ALERT_4_C           Flack test results are ambiguous.
           From the CIF: _refine_ls_abs_structure_Flack    0.536
           From the CIF: _refine_ls_abs_structure_Flack_su    0.017
PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero .......       0.54

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           27.50
           From the CIF: _reflns_number_total               2492
           Count of symmetry unique reflns         1454
           Completeness (_total/calc)            171.39%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1038
           Fraction of Friedel pairs measured     0.714
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

3-(2-Bromophenyl)isocoumarin

Crystal data

C15H9BrO2	F(000) = 600
Mr = 301.13	Dx = 1.701 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2492 reflections
a = 12.595 (6) Å	θ = 3.4–27.5°
b = 12.128 (9) Å	µ = 3.48 mm^−1
c = 7.699 (6) Å	T = 173 K
V = 1176.0 (14) Å^3	Block, colorless
Z = 4	0.16 × 0.14 × 0.10 mm

Data collection

Bruker–Nonius KappaCCD diffractometer	7105 independent reflections
Radiation source: fine-focus sealed tube	2096 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
ω and φ scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −16→15
Tmin = 0.594, Tmax = 0.708	k = −15→15
2492 measured reflections	l = −9→9

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)] = 0.038	H-atom parameters constrained
wR(F^2) = 0.094	w = 1/[σ^2(Fo^2) + (0.0492P)^2 + 0.803P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2492 reflections	Δρmax = 0.37 e Å^−3
164 parameters	Δρmin = −0.50 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1073 Fridels
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.536 (17)

Special details

Experimental. EI–MS m/z (%): 303, 301 (M⁺, 30), 165?(28), 137 (19.8), 117?(100); IR (film, ν, cm^-1): 2913, 2849, 1712, 1694, 1598, 1572, 1471, 1151, 832 cm^-1; ¹H NMR (CDCl₃): δ 6.90 (s, 1H, H-4), 7.43 (m, 1H, H-5), 7.47 (m, 1H, H-7), 7.49 (m, 1H, H-4'), 7.51 (m, 1H, H-6'), 7.69 (dt, J = 7.2, 1.8 Hz, 1H, H-6); 7.81 (dt, J = 7.8, 1.7 Hz, 1H, H-5').

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.54430 (3)	0.73308 (3)	0.79476 (12)	0.03527 (14)
O1	0.4843 (2)	0.3883 (2)	0.7077 (4)	0.0284 (6)
O2	0.3909 (2)	0.24387 (19)	0.7917 (10)	0.0367 (6)
C1	0.3881 (3)	0.3320 (3)	0.7239 (6)	0.0324 (10)
C2	0.2941 (3)	0.3891 (3)	0.6602 (6)	0.0282 (9)
C3	0.1939 (3)	0.3388 (4)	0.6767 (6)	0.0333 (9)
H3	0.1877	0.2684	0.7298	0.040*
C4	0.1049 (3)	0.3923 (4)	0.6156 (6)	0.0408 (11)
H4	0.0371	0.3590	0.6286	0.049*
C5	0.1133 (4)	0.4932 (4)	0.5362 (6)	0.0407 (12)
H5	0.0514	0.5279	0.4918	0.049*
C6	0.2118 (4)	0.5460 (4)	0.5195 (7)	0.0306 (12)
H6	0.2168	0.6161	0.4648	0.037*
C7	0.3026 (3)	0.4941 (4)	0.5847 (6)	0.0292 (10)
C8	0.4055 (3)	0.5443 (3)	0.5733 (5)	0.0268 (9)
H8	0.4130	0.6151	0.5219	0.032*
C9	0.4909 (3)	0.4918 (3)	0.6346 (5)	0.0256 (8)
C10	0.6035 (3)	0.5289 (3)	0.6275 (5)	0.0261 (8)
C11	0.6799 (4)	0.4572 (4)	0.5590 (6)	0.0330 (10)
H11	0.6583	0.3865	0.5192	0.040*
C12	0.7865 (4)	0.4862 (5)	0.5475 (7)	0.0369 (14)
H12	0.8370	0.4366	0.5000	0.044*
C13	0.8172 (3)	0.5889 (4)	0.6067 (6)	0.0366 (10)
H13	0.8895	0.6103	0.5978	0.044*
C14	0.7440 (3)	0.6617 (4)	0.6790 (6)	0.0326 (9)
H14	0.7660	0.7315	0.7219	0.039*
C15	0.6384 (3)	0.6301 (3)	0.6871 (5)	0.0291 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0370 (2)	0.02679 (19)	0.0420 (2)	0.00065 (13)	0.0000 (3)	−0.0036 (4)
O1	0.0314 (14)	0.0205 (13)	0.0335 (15)	−0.0020 (11)	−0.0018 (12)	0.0019 (12)
O2	0.0421 (14)	0.0243 (13)	0.0436 (14)	−0.0046 (9)	0.001 (3)	0.005 (2)
C1	0.035 (2)	0.027 (2)	0.035 (2)	−0.0050 (16)	0.0053 (17)	−0.0077 (17)
C2	0.032 (2)	0.0235 (19)	0.029 (2)	−0.0019 (15)	0.0018 (16)	−0.0073 (17)
C3	0.039 (2)	0.029 (2)	0.032 (2)	−0.0099 (17)	0.0071 (18)	−0.0055 (18)
C4	0.033 (2)	0.044 (3)	0.045 (3)	−0.013 (2)	0.009 (2)	−0.018 (2)
C5	0.022 (2)	0.051 (3)	0.049 (3)	0.0024 (19)	0.0008 (19)	−0.012 (2)
C6	0.026 (2)	0.031 (3)	0.035 (3)	−0.0019 (18)	−0.0024 (18)	−0.003 (2)
C7	0.030 (2)	0.030 (2)	0.028 (2)	−0.0022 (18)	−0.0008 (17)	−0.0052 (19)
C8	0.026 (2)	0.0233 (19)	0.031 (2)	0.0008 (15)	0.0028 (16)	0.0023 (17)
C9	0.031 (2)	0.0196 (17)	0.026 (2)	−0.0011 (15)	0.0002 (16)	0.0003 (15)
C10	0.025 (2)	0.0248 (19)	0.028 (2)	−0.0009 (15)	−0.0051 (16)	0.0042 (17)
C11	0.035 (2)	0.029 (2)	0.035 (3)	0.0034 (19)	−0.0011 (19)	−0.0020 (19)
C12	0.035 (3)	0.041 (3)	0.035 (3)	0.006 (2)	0.003 (2)	0.002 (2)
C13	0.027 (2)	0.041 (3)	0.041 (3)	−0.0020 (18)	−0.0012 (19)	0.004 (2)
C14	0.033 (2)	0.029 (2)	0.036 (2)	−0.0076 (17)	−0.0045 (18)	0.0047 (18)
C15	0.031 (2)	0.0251 (19)	0.031 (2)	0.0009 (15)	0.0020 (18)	0.0071 (17)

Geometric parameters (Å, º)

Br1—C15	1.911 (4)	C7—C8	1.434 (6)
O1—C9	1.378 (5)	C8—C9	1.335 (6)
O1—C1	1.396 (5)	C8—H8	0.9500
O2—C1	1.190 (6)	C9—C10	1.488 (5)
C1—C2	1.457 (6)	C10—C15	1.382 (6)
C2—C7	1.404 (6)	C10—C11	1.400 (6)
C2—C3	1.407 (5)	C11—C12	1.390 (6)
C3—C4	1.378 (6)	C11—H11	0.9500
C3—H3	0.9500	C12—C13	1.381 (8)
C4—C5	1.372 (7)	C12—H12	0.9500
C4—H4	0.9500	C13—C14	1.392 (7)
C5—C6	1.402 (7)	C13—H13	0.9500
C5—H5	0.9500	C14—C15	1.386 (6)
C6—C7	1.399 (6)	C14—H14	0.9500
C6—H6	0.9500
C9—O1—C1	122.3 (3)	C9—C8—H8	119.9
O2—C1—O1	116.9 (4)	C7—C8—H8	119.9
O2—C1—C2	126.8 (4)	C8—C9—O1	122.0 (4)
O1—C1—C2	116.3 (4)	C8—C9—C10	127.6 (4)
C7—C2—C3	119.9 (4)	O1—C9—C10	110.3 (3)
C7—C2—C1	120.6 (4)	C15—C10—C11	117.3 (4)
C3—C2—C1	119.5 (4)	C15—C10—C9	123.9 (4)
C4—C3—C2	119.6 (4)	C11—C10—C9	118.8 (4)
C4—C3—H3	120.2	C12—C11—C10	122.0 (5)
C2—C3—H3	120.2	C12—C11—H11	119.0
C5—C4—C3	120.6 (4)	C10—C11—H11	119.0
C5—C4—H4	119.7	C13—C12—C11	118.5 (5)
C3—C4—H4	119.7	C13—C12—H12	120.7
C4—C5—C6	121.1 (5)	C11—C12—H12	120.7
C4—C5—H5	119.5	C12—C13—C14	121.2 (4)
C6—C5—H5	119.5	C12—C13—H13	119.4
C7—C6—C5	119.0 (5)	C14—C13—H13	119.4
C7—C6—H6	120.5	C15—C14—C13	118.6 (4)
C5—C6—H6	120.5	C15—C14—H14	120.7
C6—C7—C2	119.6 (4)	C13—C14—H14	120.7
C6—C7—C8	121.7 (4)	C10—C15—C14	122.4 (4)
C2—C7—C8	118.6 (4)	C10—C15—Br1	121.8 (3)
C9—C8—C7	120.3 (4)	C14—C15—Br1	115.7 (3)
C9—O1—C1—O2	−178.7 (5)	C7—C8—C9—O1	1.0 (6)
C9—O1—C1—C2	−0.5 (5)	C7—C8—C9—C10	177.3 (4)
O2—C1—C2—C7	179.1 (6)	C1—O1—C9—C8	−0.6 (6)
O1—C1—C2—C7	1.0 (6)	C1—O1—C9—C10	−177.4 (3)
O2—C1—C2—C3	−0.1 (8)	C8—C9—C10—C15	53.5 (6)
O1—C1—C2—C3	−178.1 (4)	O1—C9—C10—C15	−129.9 (4)
C7—C2—C3—C4	1.2 (6)	C8—C9—C10—C11	−127.4 (5)
C1—C2—C3—C4	−179.6 (4)	O1—C9—C10—C11	49.1 (5)
C2—C3—C4—C5	1.1 (7)	C15—C10—C11—C12	−1.2 (7)
C3—C4—C5—C6	−1.9 (7)	C9—C10—C11—C12	179.7 (4)
C4—C5—C6—C7	0.3 (7)	C10—C11—C12—C13	0.4 (7)
C5—C6—C7—C2	2.0 (7)	C11—C12—C13—C14	1.0 (8)
C5—C6—C7—C8	−179.3 (5)	C12—C13—C14—C15	−1.5 (7)
C3—C2—C7—C6	−2.8 (6)	C11—C10—C15—C14	0.7 (6)
C1—C2—C7—C6	178.1 (4)	C9—C10—C15—C14	179.7 (4)
C3—C2—C7—C8	178.6 (4)	C11—C10—C15—Br1	−176.7 (3)
C1—C2—C7—C8	−0.6 (6)	C9—C10—C15—Br1	2.3 (6)
C6—C7—C8—C9	−179.1 (4)	C13—C14—C15—C10	0.6 (6)
C2—C7—C8—C9	−0.4 (6)	C13—C14—C15—Br1	178.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2^i	0.95	2.55	3.439 (6)	155
C6—H6···O2^ii	0.95	2.45	3.242 (7)	140

Symmetry codes: (i) x−1/2, −y+1/2, z; (ii) −x+1/2, y+1/2, z−1/2.