In the crystal, molecules are linked into dimers by pairs of C—H

O hydrogen bonds, thus generating

(18) rings. The crystal packing of the title compound is dominated by H

H, Br

H, H

π and Br

π interactions.
Supporting information
CCDC reference: 2060298
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.025
- wR factor = 0.059
- Data-to-parameter ratio = 23.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min). 10 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 5 Report
Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 3 Note
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note) 0.001 Degree
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records 1 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records 1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for Br2A --C2 . 5.1 s.u.
PLAT301_ALERT_3_G Main Residue Disorder ..............(Resd 1 ) 5% Note
PLAT398_ALERT_2_G Deviating C-O-C Angle From 120 for O1 97.3 Degree
PLAT434_ALERT_2_G Short Inter HL..HL Contact Br1 ..Br1 3.49 Ang.
-x,-y,1-z = 2_556 Check
PLAT793_ALERT_4_G Model has Chirality at C1 (Centro SPGR) S Verify
PLAT793_ALERT_4_G Model has Chirality at C2 (Centro SPGR) S Verify
PLAT793_ALERT_4_G Model has Chirality at C3 (Centro SPGR) R Verify
PLAT793_ALERT_4_G Model has Chirality at C5 (Centro SPGR) S Verify
PLAT793_ALERT_4_G Model has Chirality at C6 (Centro SPGR) R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 48 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ... 5 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 12 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
17 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 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
8 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).
8,9-Dibromo-7-methyl-3-phenyl-10-oxa-3-azatricyclo[5.2.1.0
1,5]decan-4-one
top
Crystal data top
C15H15Br2NO2 | Z = 2 |
Mr = 401.10 | F(000) = 396 |
Triclinic, P1 | Dx = 1.798 Mg m−3 |
a = 6.8064 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5045 (2) Å | Cell parameters from 9338 reflections |
c = 11.9482 (3) Å | θ = 2.6–29.2° |
α = 79.551 (1)° | µ = 5.47 mm−1 |
β = 87.820 (1)° | T = 296 K |
γ = 77.083 (1)° | Fragment, colourless |
V = 740.89 (3) Å3 | 0.14 × 0.13 × 0.13 mm |
Data collection top
Bruker Kappa APEXII area-detector diffractometer | 3575 reflections with I > 2σ(I) |
ω– and φ–scans | Rint = 0.025 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | θmax = 30.3°, θmin = 3.8° |
Tmin = 0.184, Tmax = 0.273 | h = −8→9 |
19111 measured reflections | k = −13→13 |
4387 independent reflections | l = −16→16 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.025 | w = 1/[σ2(Fo2) + (0.0265P)2 + 0.1676P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.059 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.34 e Å−3 |
4387 reflections | Δρmin = −0.35 e Å−3 |
187 parameters | Extinction correction: SHELXL-2018/3 (Sheldrick 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0099 (8) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
C1 | 0.2491 (2) | 0.23465 (16) | 0.29816 (13) | 0.0300 (3) | |
H1 | 0.162569 | 0.333375 | 0.282028 | 0.036* | |
C2 | 0.3412 (2) | 0.18494 (19) | 0.18835 (14) | 0.0358 (3) | |
H2 | 0.312544 | 0.089368 | 0.184511 | 0.043* | |
C3 | 0.5718 (2) | 0.16536 (17) | 0.20591 (13) | 0.0315 (3) | |
C4 | 0.6318 (2) | 0.31286 (17) | 0.19882 (13) | 0.0346 (3) | |
H4A | 0.580003 | 0.380680 | 0.130185 | 0.041* | |
H4B | 0.776935 | 0.300779 | 0.202053 | 0.041* | |
C5 | 0.5290 (2) | 0.36343 (16) | 0.30594 (13) | 0.0302 (3) | |
H5 | 0.423305 | 0.452582 | 0.285765 | 0.036* | |
C6 | 0.4389 (2) | 0.23380 (15) | 0.36065 (12) | 0.0264 (3) | |
C7 | 0.4433 (2) | 0.23050 (17) | 0.48669 (13) | 0.0289 (3) | |
H7A | 0.316869 | 0.284391 | 0.512777 | 0.035* | |
H7B | 0.470492 | 0.130584 | 0.528351 | 0.035* | |
C8 | 0.6637 (2) | 0.37833 (16) | 0.39896 (13) | 0.0303 (3) | |
C9 | 0.6869 (2) | 0.29591 (16) | 0.60907 (13) | 0.0292 (3) | |
C10 | 0.5782 (3) | 0.24987 (18) | 0.70424 (14) | 0.0356 (3) | |
H10 | 0.456428 | 0.224227 | 0.695094 | 0.043* | |
C11 | 0.6499 (3) | 0.2420 (2) | 0.81232 (15) | 0.0449 (4) | |
H11 | 0.575891 | 0.211181 | 0.875398 | 0.054* | |
C12 | 0.8306 (3) | 0.2794 (2) | 0.82762 (17) | 0.0480 (4) | |
H12 | 0.878984 | 0.273335 | 0.900469 | 0.058* | |
C13 | 0.9379 (3) | 0.3257 (2) | 0.73344 (17) | 0.0451 (4) | |
H13 | 1.059246 | 0.351480 | 0.743341 | 0.054* | |
C14 | 0.8691 (2) | 0.33463 (18) | 0.62468 (15) | 0.0374 (4) | |
H14 | 0.943622 | 0.366258 | 0.562061 | 0.045* | |
C15 | 0.7046 (3) | 0.0567 (2) | 0.14292 (16) | 0.0463 (4) | |
H15A | 0.841396 | 0.039666 | 0.168395 | 0.069* | |
H15B | 0.697046 | 0.095089 | 0.062760 | 0.069* | |
H15C | 0.660246 | −0.033910 | 0.157404 | 0.069* | |
N1 | 0.60928 (18) | 0.30218 (13) | 0.49983 (11) | 0.0289 (3) | |
O1 | 0.57998 (14) | 0.11085 (10) | 0.32711 (8) | 0.0280 (2) | |
O2 | 0.79438 (19) | 0.44882 (13) | 0.38590 (11) | 0.0435 (3) | |
Br1 | 0.10285 (2) | 0.09342 (2) | 0.38126 (2) | 0.03963 (7) | |
Br2 | 0.22893 (10) | 0.3267 (3) | 0.05089 (6) | 0.0579 (2) | 0.833 (8) |
Br2A | 0.2336 (6) | 0.2821 (8) | 0.0560 (3) | 0.0579 (2) | 0.167 (8) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0257 (7) | 0.0304 (7) | 0.0335 (8) | −0.0070 (6) | −0.0009 (6) | −0.0037 (6) |
C2 | 0.0354 (8) | 0.0430 (9) | 0.0299 (8) | −0.0118 (7) | −0.0030 (6) | −0.0043 (7) |
C3 | 0.0308 (7) | 0.0367 (8) | 0.0263 (7) | −0.0063 (6) | 0.0015 (6) | −0.0053 (6) |
C4 | 0.0350 (8) | 0.0404 (8) | 0.0284 (8) | −0.0137 (7) | 0.0021 (6) | 0.0000 (6) |
C5 | 0.0295 (7) | 0.0273 (7) | 0.0326 (8) | −0.0081 (6) | 0.0006 (6) | −0.0002 (6) |
C6 | 0.0237 (6) | 0.0262 (7) | 0.0291 (7) | −0.0060 (5) | 0.0020 (5) | −0.0044 (5) |
C7 | 0.0261 (7) | 0.0327 (7) | 0.0302 (7) | −0.0114 (6) | 0.0041 (6) | −0.0067 (6) |
C8 | 0.0300 (7) | 0.0270 (7) | 0.0344 (8) | −0.0086 (6) | 0.0022 (6) | −0.0048 (6) |
C9 | 0.0292 (7) | 0.0265 (7) | 0.0322 (8) | −0.0048 (6) | −0.0010 (6) | −0.0074 (6) |
C10 | 0.0376 (8) | 0.0386 (8) | 0.0333 (8) | −0.0148 (7) | 0.0013 (7) | −0.0060 (7) |
C11 | 0.0539 (11) | 0.0509 (10) | 0.0320 (9) | −0.0194 (8) | −0.0006 (8) | −0.0031 (7) |
C12 | 0.0547 (11) | 0.0540 (11) | 0.0369 (9) | −0.0164 (9) | −0.0127 (8) | −0.0041 (8) |
C13 | 0.0349 (9) | 0.0517 (10) | 0.0505 (11) | −0.0124 (8) | −0.0104 (8) | −0.0083 (8) |
C14 | 0.0295 (8) | 0.0424 (9) | 0.0417 (9) | −0.0092 (7) | 0.0012 (7) | −0.0096 (7) |
C15 | 0.0462 (10) | 0.0526 (10) | 0.0394 (10) | −0.0059 (8) | 0.0088 (8) | −0.0145 (8) |
N1 | 0.0282 (6) | 0.0313 (6) | 0.0298 (6) | −0.0116 (5) | 0.0019 (5) | −0.0068 (5) |
O1 | 0.0269 (5) | 0.0275 (5) | 0.0280 (5) | −0.0034 (4) | 0.0020 (4) | −0.0040 (4) |
O2 | 0.0445 (7) | 0.0450 (7) | 0.0462 (7) | −0.0265 (5) | −0.0004 (5) | −0.0003 (5) |
Br1 | 0.03119 (9) | 0.04352 (10) | 0.04675 (11) | −0.01621 (7) | 0.00310 (7) | −0.00536 (7) |
Br2 | 0.05211 (13) | 0.0780 (7) | 0.03458 (13) | −0.0074 (3) | −0.01400 (9) | 0.0075 (2) |
Br2A | 0.05211 (13) | 0.0780 (7) | 0.03458 (13) | −0.0074 (3) | −0.01400 (9) | 0.0075 (2) |
Geometric parameters (Å, º) top
C1—C6 | 1.514 (2) | C7—H7A | 0.9700 |
C1—C2 | 1.539 (2) | C7—H7B | 0.9700 |
C1—Br1 | 1.9538 (15) | C8—O2 | 1.2175 (18) |
C1—H1 | 0.9800 | C8—N1 | 1.3722 (19) |
C2—C3 | 1.556 (2) | C9—C10 | 1.390 (2) |
C2—Br2A | 1.773 (4) | C9—C14 | 1.398 (2) |
C2—Br2 | 1.982 (2) | C9—N1 | 1.413 (2) |
C2—H2 | 0.9800 | C10—C11 | 1.381 (2) |
C3—O1 | 1.4455 (18) | C10—H10 | 0.9300 |
C3—C15 | 1.504 (2) | C11—C12 | 1.381 (3) |
C3—C4 | 1.533 (2) | C11—H11 | 0.9300 |
C4—C5 | 1.537 (2) | C12—C13 | 1.377 (3) |
C4—H4A | 0.9700 | C12—H12 | 0.9300 |
C4—H4B | 0.9700 | C13—C14 | 1.380 (3) |
C5—C8 | 1.513 (2) | C13—H13 | 0.9300 |
C5—C6 | 1.529 (2) | C14—H14 | 0.9300 |
C5—H5 | 0.9800 | C15—H15A | 0.9600 |
C6—O1 | 1.4445 (16) | C15—H15B | 0.9600 |
C6—C7 | 1.502 (2) | C15—H15C | 0.9600 |
C7—N1 | 1.4699 (19) | | |
| | | |
C6—C1—C2 | 100.18 (11) | N1—C7—C6 | 102.98 (11) |
C6—C1—Br1 | 111.46 (10) | N1—C7—H7A | 111.2 |
C2—C1—Br1 | 110.81 (10) | C6—C7—H7A | 111.2 |
C6—C1—H1 | 111.3 | N1—C7—H7B | 111.2 |
C2—C1—H1 | 111.3 | C6—C7—H7B | 111.2 |
Br1—C1—H1 | 111.3 | H7A—C7—H7B | 109.1 |
C1—C2—C3 | 103.47 (12) | O2—C8—N1 | 126.42 (15) |
C1—C2—Br2A | 118.5 (2) | O2—C8—C5 | 125.35 (14) |
C3—C2—Br2A | 118.35 (18) | N1—C8—C5 | 108.22 (12) |
C1—C2—Br2 | 111.70 (12) | C10—C9—C14 | 118.90 (15) |
C3—C2—Br2 | 114.67 (11) | C10—C9—N1 | 118.84 (14) |
C1—C2—H2 | 108.9 | C14—C9—N1 | 122.25 (14) |
C3—C2—H2 | 108.9 | C11—C10—C9 | 120.38 (16) |
Br2—C2—H2 | 108.9 | C11—C10—H10 | 119.8 |
O1—C3—C15 | 110.86 (13) | C9—C10—H10 | 119.8 |
O1—C3—C4 | 101.92 (12) | C12—C11—C10 | 120.66 (17) |
C15—C3—C4 | 116.12 (14) | C12—C11—H11 | 119.7 |
O1—C3—C2 | 98.23 (11) | C10—C11—H11 | 119.7 |
C15—C3—C2 | 115.34 (14) | C13—C12—C11 | 119.02 (18) |
C4—C3—C2 | 111.95 (13) | C13—C12—H12 | 120.5 |
C3—C4—C5 | 100.86 (12) | C11—C12—H12 | 120.5 |
C3—C4—H4A | 111.6 | C12—C13—C14 | 121.36 (17) |
C5—C4—H4A | 111.6 | C12—C13—H13 | 119.3 |
C3—C4—H4B | 111.6 | C14—C13—H13 | 119.3 |
C5—C4—H4B | 111.6 | C13—C14—C9 | 119.67 (16) |
H4A—C4—H4B | 109.4 | C13—C14—H14 | 120.2 |
C8—C5—C6 | 102.91 (12) | C9—C14—H14 | 120.2 |
C8—C5—C4 | 117.40 (13) | C3—C15—H15A | 109.5 |
C6—C5—C4 | 102.89 (12) | C3—C15—H15B | 109.5 |
C8—C5—H5 | 111.0 | H15A—C15—H15B | 109.5 |
C6—C5—H5 | 111.0 | C3—C15—H15C | 109.5 |
C4—C5—H5 | 111.0 | H15A—C15—H15C | 109.5 |
O1—C6—C7 | 112.07 (12) | H15B—C15—H15C | 109.5 |
O1—C6—C1 | 102.18 (11) | C8—N1—C9 | 126.80 (13) |
C7—C6—C1 | 122.52 (12) | C8—N1—C7 | 112.86 (12) |
O1—C6—C5 | 102.27 (11) | C9—N1—C7 | 120.22 (12) |
C7—C6—C5 | 105.82 (12) | C6—O1—C3 | 97.27 (10) |
C1—C6—C5 | 110.27 (12) | | |
| | | |
C6—C1—C2—C3 | −0.64 (15) | O1—C6—C7—N1 | 85.18 (13) |
Br1—C1—C2—C3 | −118.41 (11) | C1—C6—C7—N1 | −152.93 (13) |
C6—C1—C2—Br2A | −133.9 (3) | C5—C6—C7—N1 | −25.51 (14) |
Br1—C1—C2—Br2A | 108.3 (3) | C6—C5—C8—O2 | 164.98 (15) |
C6—C1—C2—Br2 | −124.51 (12) | C4—C5—C8—O2 | 52.9 (2) |
Br1—C1—C2—Br2 | 117.72 (11) | C6—C5—C8—N1 | −16.51 (15) |
C1—C2—C3—O1 | 35.54 (14) | C4—C5—C8—N1 | −128.64 (14) |
Br2A—C2—C3—O1 | 168.9 (3) | C14—C9—C10—C11 | −0.3 (2) |
Br2—C2—C3—O1 | 157.45 (12) | N1—C9—C10—C11 | 179.79 (15) |
C1—C2—C3—C15 | 153.36 (14) | C9—C10—C11—C12 | −0.1 (3) |
Br2A—C2—C3—C15 | −73.3 (3) | C10—C11—C12—C13 | 0.4 (3) |
Br2—C2—C3—C15 | −84.74 (17) | C11—C12—C13—C14 | −0.3 (3) |
C1—C2—C3—C4 | −70.91 (15) | C12—C13—C14—C9 | −0.1 (3) |
Br2A—C2—C3—C4 | 62.4 (3) | C10—C9—C14—C13 | 0.4 (2) |
Br2—C2—C3—C4 | 50.99 (17) | N1—C9—C14—C13 | −179.71 (15) |
O1—C3—C4—C5 | −36.84 (14) | O2—C8—N1—C9 | 3.2 (3) |
C15—C3—C4—C5 | −157.42 (14) | C5—C8—N1—C9 | −175.27 (13) |
C2—C3—C4—C5 | 67.22 (15) | O2—C8—N1—C7 | 179.05 (15) |
C3—C4—C5—C8 | 115.57 (14) | C5—C8—N1—C7 | 0.57 (17) |
C3—C4—C5—C6 | 3.44 (14) | C10—C9—N1—C8 | 161.81 (15) |
C2—C1—C6—O1 | −34.97 (13) | C14—C9—N1—C8 | −18.1 (2) |
Br1—C1—C6—O1 | 82.31 (11) | C10—C9—N1—C7 | −13.8 (2) |
C2—C1—C6—C7 | −161.36 (13) | C14—C9—N1—C7 | 166.34 (14) |
Br1—C1—C6—C7 | −44.08 (16) | C6—C7—N1—C8 | 15.92 (16) |
C2—C1—C6—C5 | 73.18 (14) | C6—C7—N1—C9 | −167.93 (12) |
Br1—C1—C6—C5 | −169.54 (10) | C7—C6—O1—C3 | −167.25 (12) |
C8—C5—C6—O1 | −91.53 (13) | C1—C6—O1—C3 | 59.84 (12) |
C4—C5—C6—O1 | 30.94 (14) | C5—C6—O1—C3 | −54.35 (13) |
C8—C5—C6—C7 | 25.94 (15) | C15—C3—O1—C6 | −178.76 (13) |
C4—C5—C6—C7 | 148.41 (12) | C4—C3—O1—C6 | 57.05 (12) |
C8—C5—C6—C1 | 160.39 (12) | C2—C3—O1—C6 | −57.57 (12) |
C4—C5—C6—C1 | −77.14 (14) | | |
Hydrogen-bond geometry (Å, º) topCg5 is the centroid of the C9–C14 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···Br2 | 0.97 | 2.79 | 3.2838 (17) | 113 |
C13—H13···O2i | 0.93 | 2.58 | 3.223 (2) | 127 |
C14—H14···O2 | 0.93 | 2.30 | 2.884 (2) | 120 |
C5—H5···Cg5ii | 0.98 | 2.49 | 3.4195 (17) | 158 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1. |
Summary of short interatomic contacts (Å) in the title compound topContact | Distance | Symmetry operation |
H7A···H14 | 2.56 | -1 + x, y, z |
Br1···Br1 | 3.4852 (3) | -x, -y, 1 - z |
H15C···H10 | 2.53 | 1 - x, -y, 1 - z |
H15B···H11 | 2.40 | x, y, -1 + z |
Br2A···H12 | 3.13 | -1 + x, y, -1 + z |
H5···C14 | 2.83 | 1 - x, 1 - y, 1 - z |
H13···O2 | 2.58 | 2 - x, 1 - y, 1 - z |
Percentage contributions of interatomic contacts to the
Hirshfeld surface for the title compound topContact | Percentage contribution |
H···H | 43.0 |
Br···H/H···Br | 21.1 |
C···H/H···C | 12.4 |
O···H/H···O | 11.9 |
Br···C/C···Br | 3.5 |
Br···Br | 2.9 |
Br···O/O···Br | 2.5 |
Br···N/N···Br | 1.1 |
C···C | 0.5 |
C···N/N···C | 0.5 |
C···O/O···C | 0.3 |
N···O/O···N | 0.1 |
N···N | 0.1 |