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The molecular structure of the title compound, C
15H
9BrO
2, 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.
Supporting information
CCDC reference: 618264
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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
top
Crystal data top
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) Å3 | Block, colorless |
Z = 4 | 0.16 × 0.14 × 0.10 mm |
Data collection top
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 top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.803P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O2i | 0.95 | 2.55 | 3.439 (6) | 155 |
C6—H6···O2ii | 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. |
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