

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040627/bt2482sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040627/bt2482Isup2.hkl |
CCDC reference: 660322
1 was prepared as described previously (Nakanishi & Hayashi, 2002) and crystallized from dichloromethane/hexane.
All H atoms were included in calculated positions (C—H = 0.95 Å) and were refined as riding atoms with Uiso(H) = 1.2 Ueq(C).
For examples of sterically crowded 1,8 naphthalenes, see: Nakanishi & Hayashi (2002); Aucott et al. (2004).
Data collection: SCXmini (Rigaku, 2006); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2006); software used to prepare material for publication: CrystalStructure.
![]() | Fig. 1. The structure of (1) with displacement ellipsoids drawn at the 50% probability level, hydrogen atoms omitted for clarity. |
C16H11BrSe | F(000) = 704.00 |
Mr = 362.13 | Dx = 1.810 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ybc | Cell parameters from 12100 reflections |
a = 12.2378 (6) Å | θ = 3.1–27.6° |
b = 7.8921 (4) Å | µ = 5.82 mm−1 |
c = 14.7367 (8) Å | T = 125 K |
β = 110.980 (1)° | Platelet, colourless |
V = 1328.94 (12) Å3 | 0.40 × 0.16 × 0.13 mm |
Z = 4 |
Rigaku SCXmini diffractometer | 2043 reflections with F2 > 2σ(F2) |
Detector resolution: 6.85 pixels mm-1 | Rint = 0.052 |
ω scans | θmax = 25.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −14→14 |
Tmin = 0.220, Tmax = 0.469 | k = −9→9 |
10966 measured reflections | l = −17→17 |
2337 independent reflections |
Refinement on F2 | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.033 | w = 1/[σ2(Fo2) + (0.0275P)2 + 0.7022P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.067 | (Δ/σ)max = 0.001 |
S = 1.08 | Δρmax = 0.47 e Å−3 |
2337 reflections | Δρmin = −0.35 e Å−3 |
164 parameters |
C16H11BrSe | V = 1328.94 (12) Å3 |
Mr = 362.13 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.2378 (6) Å | µ = 5.82 mm−1 |
b = 7.8921 (4) Å | T = 125 K |
c = 14.7367 (8) Å | 0.40 × 0.16 × 0.13 mm |
β = 110.980 (1)° |
Rigaku SCXmini diffractometer | 2337 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2043 reflections with F2 > 2σ(F2) |
Tmin = 0.220, Tmax = 0.469 | Rint = 0.052 |
10966 measured reflections |
R[F2 > 2σ(F2)] = 0.033 | 164 parameters |
wR(F2) = 0.067 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.47 e Å−3 |
2337 reflections | Δρmin = −0.35 e Å−3 |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.80907 (3) | 1.30949 (5) | 1.08664 (3) | 0.02935 (13) | |
Se9 | 0.84102 (3) | 1.01534 (4) | 0.95754 (3) | 0.02578 (12) | |
C1 | 0.6476 (3) | 1.2463 (4) | 1.0269 (2) | 0.0221 (7) | |
C2 | 0.5766 (3) | 1.3160 (4) | 1.0701 (2) | 0.0275 (8) | |
C3 | 0.4554 (3) | 1.2950 (4) | 1.0284 (2) | 0.0295 (9) | |
C4 | 0.4080 (3) | 1.2124 (4) | 0.9428 (2) | 0.0266 (8) | |
C5 | 0.4810 (3) | 1.1365 (4) | 0.8965 (2) | 0.0232 (8) | |
C6 | 0.4278 (3) | 1.0509 (4) | 0.8072 (2) | 0.0264 (8) | |
C7 | 0.4950 (3) | 0.9717 (4) | 0.7629 (2) | 0.0244 (8) | |
C8 | 0.6160 (3) | 0.9719 (4) | 0.8073 (2) | 0.0242 (8) | |
C9 | 0.6731 (2) | 1.0525 (4) | 0.8952 (2) | 0.0222 (7) | |
C10 | 0.6061 (2) | 1.1454 (3) | 0.9404 (2) | 0.0197 (7) | |
C11 | 0.8593 (3) | 0.8208 (4) | 0.8845 (2) | 0.0229 (7) | |
C12 | 0.8590 (3) | 0.6595 (4) | 0.9222 (2) | 0.0278 (8) | |
C13 | 0.8799 (3) | 0.5192 (4) | 0.8747 (3) | 0.0359 (9) | |
C14 | 0.9009 (3) | 0.5404 (5) | 0.7892 (3) | 0.0374 (10) | |
C15 | 0.9007 (3) | 0.7004 (5) | 0.7512 (2) | 0.0351 (10) | |
C16 | 0.8812 (3) | 0.8409 (4) | 0.7994 (2) | 0.0302 (8) | |
H2 | 0.6095 | 1.3789 | 1.1285 | 0.033* | |
H3 | 0.4063 | 1.3388 | 1.0602 | 0.035* | |
H4 | 0.3253 | 1.2044 | 0.9130 | 0.032* | |
H6 | 0.3449 | 1.0483 | 0.7777 | 0.032* | |
H7 | 0.4590 | 0.9170 | 0.7020 | 0.029* | |
H8 | 0.6614 | 0.9145 | 0.7764 | 0.029* | |
H12 | 0.8443 | 0.6455 | 0.9809 | 0.033* | |
H13 | 0.8800 | 0.4090 | 0.9006 | 0.043* | |
H14 | 0.9154 | 0.4442 | 0.7564 | 0.045* | |
H15 | 0.9139 | 0.7139 | 0.6919 | 0.042* | |
H16 | 0.8829 | 0.9512 | 0.7740 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0282 (2) | 0.0288 (2) | 0.0277 (2) | −0.00345 (16) | 0.00590 (17) | −0.00670 (15) |
Se9 | 0.0200 (2) | 0.0255 (2) | 0.0294 (2) | 0.00067 (15) | 0.00594 (17) | −0.00458 (16) |
C1 | 0.027 (2) | 0.0157 (17) | 0.0219 (19) | −0.0002 (14) | 0.0065 (16) | 0.0055 (14) |
C2 | 0.041 (2) | 0.0201 (19) | 0.026 (2) | −0.0010 (16) | 0.0177 (18) | 0.0012 (15) |
C3 | 0.037 (2) | 0.024 (2) | 0.034 (2) | 0.0054 (17) | 0.0190 (19) | 0.0050 (16) |
C4 | 0.023 (2) | 0.026 (2) | 0.033 (2) | 0.0014 (15) | 0.0124 (17) | 0.0076 (16) |
C5 | 0.028 (2) | 0.0168 (17) | 0.0260 (19) | 0.0022 (15) | 0.0108 (16) | 0.0066 (14) |
C6 | 0.0206 (19) | 0.027 (2) | 0.028 (2) | −0.0006 (15) | 0.0048 (17) | 0.0045 (16) |
C7 | 0.026 (2) | 0.0259 (19) | 0.0174 (18) | −0.0074 (16) | 0.0034 (16) | −0.0030 (15) |
C8 | 0.027 (2) | 0.0256 (19) | 0.0231 (19) | 0.0044 (15) | 0.0124 (17) | 0.0009 (15) |
C9 | 0.0188 (18) | 0.0223 (18) | 0.0248 (19) | 0.0014 (14) | 0.0070 (16) | 0.0043 (15) |
C10 | 0.0243 (19) | 0.0151 (17) | 0.0205 (18) | −0.0001 (14) | 0.0091 (15) | 0.0058 (14) |
C11 | 0.0191 (19) | 0.0242 (19) | 0.0230 (19) | 0.0028 (14) | 0.0047 (15) | −0.0028 (14) |
C12 | 0.025 (2) | 0.029 (2) | 0.028 (2) | 0.0032 (16) | 0.0069 (17) | −0.0017 (16) |
C13 | 0.027 (2) | 0.028 (2) | 0.045 (2) | 0.0028 (17) | 0.0039 (19) | −0.0043 (18) |
C14 | 0.017 (2) | 0.042 (2) | 0.050 (2) | 0.0001 (17) | 0.0076 (19) | −0.024 (2) |
C15 | 0.021 (2) | 0.060 (2) | 0.026 (2) | −0.0035 (19) | 0.0098 (17) | −0.0071 (19) |
C16 | 0.023 (2) | 0.036 (2) | 0.033 (2) | −0.0002 (17) | 0.0127 (18) | 0.0042 (17) |
Br1—C1 | 1.919 (3) | C12—C13 | 1.381 (5) |
Se9—C9 | 1.949 (3) | C13—C14 | 1.383 (6) |
Se9—C11 | 1.933 (3) | C14—C15 | 1.381 (6) |
C1—C2 | 1.362 (6) | C15—C16 | 1.383 (5) |
C1—C10 | 1.434 (4) | C2—H2 | 0.950 |
C2—C3 | 1.397 (5) | C3—H3 | 0.950 |
C3—C4 | 1.352 (4) | C4—H4 | 0.950 |
C4—C5 | 1.435 (6) | C6—H6 | 0.950 |
C5—C6 | 1.414 (4) | C7—H7 | 0.950 |
C5—C10 | 1.434 (4) | C8—H8 | 0.950 |
C6—C7 | 1.371 (5) | C12—H12 | 0.950 |
C7—C8 | 1.388 (4) | C13—H13 | 0.950 |
C8—C9 | 1.387 (4) | C14—H14 | 0.950 |
C9—C10 | 1.430 (5) | C15—H15 | 0.950 |
C11—C12 | 1.390 (5) | C16—H16 | 0.950 |
C11—C16 | 1.383 (5) | ||
Br1···C14i | 3.564 (3) | H2···H16vi | 3.528 |
Br1···C15i | 3.501 (3) | H3···C1ii | 3.493 |
C2···C3ii | 3.358 (4) | H3···C2ii | 3.383 |
C2···C6iii | 3.425 (5) | H3···C7iii | 3.465 |
C3···C2ii | 3.358 (4) | H3···C7vi | 3.164 |
C3···C5iii | 3.579 (4) | H3···C8iii | 3.206 |
C3···C6iii | 3.590 (4) | H3···C9iii | 3.372 |
C3···C7iii | 3.595 (5) | H3···C12iii | 3.348 |
C3···C8iii | 3.546 (5) | H3···H2ii | 3.515 |
C3···C9iii | 3.540 (5) | H3···H7vi | 2.744 |
C4···C5iii | 3.568 (4) | H3···H8iii | 3.451 |
C4···C9iii | 3.571 (5) | H3···H12iii | 2.909 |
C4···C10iii | 3.343 (4) | H4···C9iii | 3.474 |
C5···C3iii | 3.579 (4) | H4···C10iii | 3.420 |
C5···C4iii | 3.568 (4) | H4···C14vii | 3.508 |
C6···C2iii | 3.425 (5) | H4···C15vii | 2.951 |
C6···C3iii | 3.590 (4) | H4···C16vii | 3.417 |
C7···C3iii | 3.595 (5) | H4···H2ii | 3.489 |
C8···C3iii | 3.546 (5) | H4···H8vii | 3.299 |
C9···C3iii | 3.540 (5) | H4···H12iii | 3.238 |
C9···C4iii | 3.571 (5) | H4···H15vii | 2.779 |
C10···C4iii | 3.343 (4) | H4···H16vii | 3.584 |
C14···Br1i | 3.564 (3) | H6···C2iii | 3.560 |
C15···Br1i | 3.501 (3) | H6···C11vii | 3.508 |
Br1···H12iv | 3.183 | H6···C12vii | 3.227 |
Br1···H13iv | 3.254 | H6···C13vii | 2.871 |
Br1···H14v | 3.104 | H6···C14vii | 2.810 |
Br1···H16vi | 3.197 | H6···C15vii | 3.120 |
Se9···H13iv | 3.297 | H6···C16vii | 3.468 |
C1···H3ii | 3.493 | H6···H8vii | 2.992 |
C1···H7vii | 3.427 | H6···H13vii | 3.242 |
C2···H3ii | 3.383 | H6···H14vii | 3.151 |
C2···H6iii | 3.560 | H6···H15vii | 3.599 |
C2···H7vi | 3.507 | H7···C1ix | 3.427 |
C2···H8vi | 3.547 | H7···C2viii | 3.507 |
C3···H2ii | 3.360 | H7···C3viii | 3.411 |
C3···H7vi | 3.411 | H7···C4ix | 3.507 |
C4···H2ii | 3.376 | H7···C5ix | 2.883 |
C4···H7vii | 3.507 | H7···C6ix | 3.228 |
C4···H8vii | 3.426 | H7···C7ix | 3.567 |
C5···H7vii | 2.883 | H7···C9ix | 3.359 |
C5···H8vii | 3.341 | H7···C10ix | 2.904 |
C6···H2iii | 3.595 | H7···H2viii | 2.931 |
C6···H7vii | 3.228 | H7···H3viii | 2.744 |
C6···H8vii | 3.159 | H8···C2viii | 3.547 |
C7···H2viii | 3.043 | H8···C4ix | 3.426 |
C7···H3iii | 3.465 | H8···C5ix | 3.341 |
C7···H3viii | 3.164 | H8···C6ix | 3.159 |
C7···H7vii | 3.567 | H8···H2viii | 2.611 |
C8···H2viii | 2.861 | H8···H3iii | 3.451 |
C8···H3iii | 3.206 | H8···H4ix | 3.299 |
C9···H3iii | 3.372 | H8···H6ix | 2.992 |
C9···H4iii | 3.474 | H12···Br1xiii | 3.183 |
C9···H7vii | 3.359 | H12···C13x | 3.530 |
C10···H4iii | 3.420 | H12···H3iii | 2.909 |
C10···H7vii | 2.904 | H12···H4iii | 3.238 |
C11···H6ix | 3.508 | H12···H13x | 3.225 |
C12···H3iii | 3.348 | H12···H15v | 3.119 |
C12···H6ix | 3.227 | H13···Br1xiii | 3.254 |
C12···H13x | 3.367 | H13···Se9xiii | 3.297 |
C13···H6ix | 2.871 | H13···C12x | 3.367 |
C13···H12x | 3.530 | H13···C13x | 3.598 |
C13···H13x | 3.598 | H13···H6ix | 3.242 |
C14···H4ix | 3.508 | H13···H12x | 3.225 |
C14···H6ix | 2.810 | H14···Br1xiv | 3.104 |
C14···H15xi | 3.377 | H14···C15xi | 2.994 |
C14···H16xi | 3.183 | H14···C16xi | 3.000 |
C15···H4ix | 2.951 | H14···H6ix | 3.151 |
C15···H6ix | 3.120 | H14···H15xi | 2.666 |
C15···H14xii | 2.994 | H14···H16xi | 2.662 |
C15···H16xi | 3.424 | H15···C14xii | 3.377 |
C16···H4ix | 3.417 | H15···H4ix | 2.779 |
C16···H6ix | 3.468 | H15···H6ix | 3.599 |
C16···H14xii | 3.000 | H15···H12xiv | 3.119 |
H2···C3ii | 3.360 | H15···H14xii | 2.666 |
H2···C4ii | 3.376 | H15···H16xi | 3.137 |
H2···C6iii | 3.595 | H16···Br1viii | 3.197 |
H2···C7vi | 3.043 | H16···C14xii | 3.183 |
H2···C8vi | 2.861 | H16···C15xii | 3.424 |
H2···H3ii | 3.515 | H16···H2viii | 3.528 |
H2···H4ii | 3.489 | H16···H4ix | 3.584 |
H2···H7vi | 2.931 | H16···H14xii | 2.662 |
H2···H8vi | 2.611 | H16···H15xii | 3.137 |
C9—Se9—C11 | 99.77 (14) | C14—C15—C16 | 120.0 (4) |
Br1—C1—C2 | 113.9 (2) | C11—C16—C15 | 119.9 (3) |
Br1—C1—C10 | 122.1 (3) | C1—C2—H2 | 120.0 |
C2—C1—C10 | 123.9 (3) | C3—C2—H2 | 120.0 |
C1—C2—C3 | 120.1 (3) | C2—C3—H3 | 120.0 |
C2—C3—C4 | 120.1 (4) | C4—C3—H3 | 120.0 |
C3—C4—C5 | 120.8 (3) | C3—C4—H4 | 119.6 |
C4—C5—C6 | 118.9 (3) | C5—C4—H4 | 119.6 |
C4—C5—C10 | 120.8 (2) | C5—C6—H6 | 119.8 |
C6—C5—C10 | 120.3 (3) | C7—C6—H6 | 119.8 |
C5—C6—C7 | 120.4 (3) | C6—C7—H7 | 120.1 |
C6—C7—C8 | 119.7 (3) | C8—C7—H7 | 120.1 |
C7—C8—C9 | 122.5 (3) | C7—C8—H8 | 118.8 |
Se9—C9—C8 | 117.7 (2) | C9—C8—H8 | 118.8 |
Se9—C9—C10 | 122.8 (2) | C11—C12—H12 | 119.9 |
C8—C9—C10 | 119.2 (2) | C13—C12—H12 | 119.9 |
C1—C10—C5 | 114.1 (3) | C12—C13—H13 | 120.2 |
C1—C10—C9 | 128.3 (3) | C14—C13—H13 | 120.2 |
C5—C10—C9 | 117.6 (2) | C13—C14—H14 | 119.8 |
Se9—C11—C12 | 119.2 (3) | C15—C14—H14 | 119.8 |
Se9—C11—C16 | 120.8 (2) | C14—C15—H15 | 120.0 |
C12—C11—C16 | 119.8 (3) | C16—C15—H15 | 120.0 |
C11—C12—C13 | 120.3 (4) | C11—C16—H16 | 120.0 |
C12—C13—C14 | 119.6 (3) | C15—C16—H16 | 120.0 |
C13—C14—C15 | 120.4 (4) | ||
C9—Se9—C11—C12 | −96.0 (2) | C6—C5—C10—C9 | −5.5 (4) |
C9—Se9—C11—C16 | 88.8 (2) | C10—C5—C6—C7 | 1.7 (5) |
C11—Se9—C9—C8 | −14.9 (3) | C5—C6—C7—C8 | 1.7 (5) |
C11—Se9—C9—C10 | 159.1 (2) | C6—C7—C8—C9 | −1.2 (5) |
Br1—C1—C2—C3 | 173.5 (2) | C7—C8—C9—Se9 | 171.6 (2) |
Br1—C1—C10—C5 | −169.3 (2) | C7—C8—C9—C10 | −2.7 (5) |
Br1—C1—C10—C9 | 12.1 (5) | Se9—C9—C10—C1 | 10.6 (5) |
C2—C1—C10—C5 | 5.8 (4) | Se9—C9—C10—C5 | −168.0 (2) |
C2—C1—C10—C9 | −172.9 (3) | C8—C9—C10—C1 | −175.5 (3) |
C10—C1—C2—C3 | −1.9 (5) | C8—C9—C10—C5 | 5.9 (4) |
C1—C2—C3—C4 | −3.1 (5) | Se9—C11—C12—C13 | −175.5 (2) |
C2—C3—C4—C5 | 3.8 (5) | Se9—C11—C16—C15 | 176.3 (2) |
C3—C4—C5—C6 | 179.8 (3) | C12—C11—C16—C15 | 1.1 (4) |
C3—C4—C5—C10 | 0.5 (5) | C16—C11—C12—C13 | −0.3 (4) |
C4—C5—C6—C7 | −177.6 (3) | C11—C12—C13—C14 | −0.2 (4) |
C4—C5—C10—C1 | −5.0 (4) | C12—C13—C14—C15 | −0.1 (3) |
C4—C5—C10—C9 | 173.8 (3) | C13—C14—C15—C16 | 1.0 (5) |
C6—C5—C10—C1 | 175.7 (3) | C14—C15—C16—C11 | −1.5 (5) |
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+1, −y+3, −z+2; (iii) −x+1, −y+2, −z+2; (iv) x, y+1, z; (v) x, −y+3/2, z+1/2; (vi) x, −y+5/2, z+1/2; (vii) −x+1, y+1/2, −z+3/2; (viii) x, −y+5/2, z−1/2; (ix) −x+1, y−1/2, −z+3/2; (x) −x+2, −y+1, −z+2; (xi) −x+2, y−1/2, −z+3/2; (xii) −x+2, y+1/2, −z+3/2; (xiii) x, y−1, z; (xiv) x, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H11BrSe |
Mr | 362.13 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 125 |
a, b, c (Å) | 12.2378 (6), 7.8921 (4), 14.7367 (8) |
β (°) | 110.980 (1) |
V (Å3) | 1328.94 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 5.82 |
Crystal size (mm) | 0.40 × 0.16 × 0.13 |
Data collection | |
Diffractometer | Rigaku SCXmini |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.220, 0.469 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 10966, 2337, 2043 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.067, 1.08 |
No. of reflections | 2337 |
No. of parameters | 164 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.47, −0.35 |
Computer programs: SCXmini (Rigaku, 2006), PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CrystalStructure (Rigaku/MSC, 2006), CrystalStructure.
Br1—C1 | 1.919 (3) | C1—C10 | 1.434 (4) |
Se9—C9 | 1.949 (3) | C9—C10 | 1.430 (5) |
Se9—C11 | 1.933 (3) | ||
C9—Se9—C11 | 99.77 (14) | Se9—C9—C8 | 117.7 (2) |
Br1—C1—C2 | 113.9 (2) | Se9—C9—C10 | 122.8 (2) |
Br1—C1—C10 | 122.1 (3) | C1—C10—C9 | 128.3 (3) |