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In the crystal, mol­ecules are linked into dimers by pairs of C—H...O hydrogen bonds, thus generating R_{2}^{2}(18) rings. The crystal packing of the title compound is dominated by H...H, Br...H, H...π and Br...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698902100116X/yk2144sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698902100116X/yk2144Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698902100116X/yk2144Isup3.cml
Supplementary material

CCDC reference: 2060298

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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

Computing details top

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[5.2.1.01,5]decan-4-one top
Crystal data top
C15H15Br2NO2Z = 2
Mr = 401.10F(000) = 396
Triclinic, P1Dx = 1.798 Mg m3
a = 6.8064 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.5045 (2) ÅCell parameters from 9338 reflections
c = 11.9482 (3) Åθ = 2.6–29.2°
α = 79.551 (1)°µ = 5.47 mm1
β = 87.820 (1)°T = 296 K
γ = 77.083 (1)°Fragment, colourless
V = 740.89 (3) Å30.14 × 0.13 × 0.13 mm
Data collection top
Bruker Kappa APEXII area-detector
diffractometer
3575 reflections with I > 2σ(I)
ω– and φ–scansRint = 0.025
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
θmax = 30.3°, θmin = 3.8°
Tmin = 0.184, Tmax = 0.273h = 89
19111 measured reflectionsk = 1313
4387 independent reflectionsl = 1616
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.05Δρmax = 0.34 e Å3
4387 reflectionsΔρmin = 0.35 e Å3
187 parametersExtinction correction: SHELXL-2018/3 (Sheldrick 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction 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
xyzUiso*/UeqOcc. (<1)
C10.2491 (2)0.23465 (16)0.29816 (13)0.0300 (3)
H10.1625690.3333750.2820280.036*
C20.3412 (2)0.18494 (19)0.18835 (14)0.0358 (3)
H20.3125440.0893680.1845110.043*
C30.5718 (2)0.16536 (17)0.20591 (13)0.0315 (3)
C40.6318 (2)0.31286 (17)0.19882 (13)0.0346 (3)
H4A0.5800030.3806800.1301850.041*
H4B0.7769350.3007790.2020530.041*
C50.5290 (2)0.36343 (16)0.30594 (13)0.0302 (3)
H50.4233050.4525820.2857650.036*
C60.4389 (2)0.23380 (15)0.36065 (12)0.0264 (3)
C70.4433 (2)0.23050 (17)0.48669 (13)0.0289 (3)
H7A0.3168690.2843910.5127770.035*
H7B0.4704920.1305840.5283510.035*
C80.6637 (2)0.37833 (16)0.39896 (13)0.0303 (3)
C90.6869 (2)0.29591 (16)0.60907 (13)0.0292 (3)
C100.5782 (3)0.24987 (18)0.70424 (14)0.0356 (3)
H100.4564280.2242270.6950940.043*
C110.6499 (3)0.2420 (2)0.81232 (15)0.0449 (4)
H110.5758910.2111810.8753980.054*
C120.8306 (3)0.2794 (2)0.82762 (17)0.0480 (4)
H120.8789840.2733350.9004690.058*
C130.9379 (3)0.3257 (2)0.73344 (17)0.0451 (4)
H131.0592460.3514800.7433410.054*
C140.8691 (2)0.33463 (18)0.62468 (15)0.0374 (4)
H140.9436220.3662580.5620610.045*
C150.7046 (3)0.0567 (2)0.14292 (16)0.0463 (4)
H15A0.8413960.0396660.1683950.069*
H15B0.6970460.0950890.0627600.069*
H15C0.6602460.0339100.1574040.069*
N10.60928 (18)0.30218 (13)0.49983 (11)0.0289 (3)
O10.57998 (14)0.11085 (10)0.32711 (8)0.0280 (2)
O20.79438 (19)0.44882 (13)0.38590 (11)0.0435 (3)
Br10.10285 (2)0.09342 (2)0.38126 (2)0.03963 (7)
Br20.22893 (10)0.3267 (3)0.05089 (6)0.0579 (2)0.833 (8)
Br2A0.2336 (6)0.2821 (8)0.0560 (3)0.0579 (2)0.167 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0257 (7)0.0304 (7)0.0335 (8)0.0070 (6)0.0009 (6)0.0037 (6)
C20.0354 (8)0.0430 (9)0.0299 (8)0.0118 (7)0.0030 (6)0.0043 (7)
C30.0308 (7)0.0367 (8)0.0263 (7)0.0063 (6)0.0015 (6)0.0053 (6)
C40.0350 (8)0.0404 (8)0.0284 (8)0.0137 (7)0.0021 (6)0.0000 (6)
C50.0295 (7)0.0273 (7)0.0326 (8)0.0081 (6)0.0006 (6)0.0002 (6)
C60.0237 (6)0.0262 (7)0.0291 (7)0.0060 (5)0.0020 (5)0.0044 (5)
C70.0261 (7)0.0327 (7)0.0302 (7)0.0114 (6)0.0041 (6)0.0067 (6)
C80.0300 (7)0.0270 (7)0.0344 (8)0.0086 (6)0.0022 (6)0.0048 (6)
C90.0292 (7)0.0265 (7)0.0322 (8)0.0048 (6)0.0010 (6)0.0074 (6)
C100.0376 (8)0.0386 (8)0.0333 (8)0.0148 (7)0.0013 (7)0.0060 (7)
C110.0539 (11)0.0509 (10)0.0320 (9)0.0194 (8)0.0006 (8)0.0031 (7)
C120.0547 (11)0.0540 (11)0.0369 (9)0.0164 (9)0.0127 (8)0.0041 (8)
C130.0349 (9)0.0517 (10)0.0505 (11)0.0124 (8)0.0104 (8)0.0083 (8)
C140.0295 (8)0.0424 (9)0.0417 (9)0.0092 (7)0.0012 (7)0.0096 (7)
C150.0462 (10)0.0526 (10)0.0394 (10)0.0059 (8)0.0088 (8)0.0145 (8)
N10.0282 (6)0.0313 (6)0.0298 (6)0.0116 (5)0.0019 (5)0.0068 (5)
O10.0269 (5)0.0275 (5)0.0280 (5)0.0034 (4)0.0020 (4)0.0040 (4)
O20.0445 (7)0.0450 (7)0.0462 (7)0.0265 (5)0.0004 (5)0.0003 (5)
Br10.03119 (9)0.04352 (10)0.04675 (11)0.01621 (7)0.00310 (7)0.00536 (7)
Br20.05211 (13)0.0780 (7)0.03458 (13)0.0074 (3)0.01400 (9)0.0075 (2)
Br2A0.05211 (13)0.0780 (7)0.03458 (13)0.0074 (3)0.01400 (9)0.0075 (2)
Geometric parameters (Å, º) top
C1—C61.514 (2)C7—H7A0.9700
C1—C21.539 (2)C7—H7B0.9700
C1—Br11.9538 (15)C8—O21.2175 (18)
C1—H10.9800C8—N11.3722 (19)
C2—C31.556 (2)C9—C101.390 (2)
C2—Br2A1.773 (4)C9—C141.398 (2)
C2—Br21.982 (2)C9—N11.413 (2)
C2—H20.9800C10—C111.381 (2)
C3—O11.4455 (18)C10—H100.9300
C3—C151.504 (2)C11—C121.381 (3)
C3—C41.533 (2)C11—H110.9300
C4—C51.537 (2)C12—C131.377 (3)
C4—H4A0.9700C12—H120.9300
C4—H4B0.9700C13—C141.380 (3)
C5—C81.513 (2)C13—H130.9300
C5—C61.529 (2)C14—H140.9300
C5—H50.9800C15—H15A0.9600
C6—O11.4445 (16)C15—H15B0.9600
C6—C71.502 (2)C15—H15C0.9600
C7—N11.4699 (19)
C6—C1—C2100.18 (11)N1—C7—C6102.98 (11)
C6—C1—Br1111.46 (10)N1—C7—H7A111.2
C2—C1—Br1110.81 (10)C6—C7—H7A111.2
C6—C1—H1111.3N1—C7—H7B111.2
C2—C1—H1111.3C6—C7—H7B111.2
Br1—C1—H1111.3H7A—C7—H7B109.1
C1—C2—C3103.47 (12)O2—C8—N1126.42 (15)
C1—C2—Br2A118.5 (2)O2—C8—C5125.35 (14)
C3—C2—Br2A118.35 (18)N1—C8—C5108.22 (12)
C1—C2—Br2111.70 (12)C10—C9—C14118.90 (15)
C3—C2—Br2114.67 (11)C10—C9—N1118.84 (14)
C1—C2—H2108.9C14—C9—N1122.25 (14)
C3—C2—H2108.9C11—C10—C9120.38 (16)
Br2—C2—H2108.9C11—C10—H10119.8
O1—C3—C15110.86 (13)C9—C10—H10119.8
O1—C3—C4101.92 (12)C12—C11—C10120.66 (17)
C15—C3—C4116.12 (14)C12—C11—H11119.7
O1—C3—C298.23 (11)C10—C11—H11119.7
C15—C3—C2115.34 (14)C13—C12—C11119.02 (18)
C4—C3—C2111.95 (13)C13—C12—H12120.5
C3—C4—C5100.86 (12)C11—C12—H12120.5
C3—C4—H4A111.6C12—C13—C14121.36 (17)
C5—C4—H4A111.6C12—C13—H13119.3
C3—C4—H4B111.6C14—C13—H13119.3
C5—C4—H4B111.6C13—C14—C9119.67 (16)
H4A—C4—H4B109.4C13—C14—H14120.2
C8—C5—C6102.91 (12)C9—C14—H14120.2
C8—C5—C4117.40 (13)C3—C15—H15A109.5
C6—C5—C4102.89 (12)C3—C15—H15B109.5
C8—C5—H5111.0H15A—C15—H15B109.5
C6—C5—H5111.0C3—C15—H15C109.5
C4—C5—H5111.0H15A—C15—H15C109.5
O1—C6—C7112.07 (12)H15B—C15—H15C109.5
O1—C6—C1102.18 (11)C8—N1—C9126.80 (13)
C7—C6—C1122.52 (12)C8—N1—C7112.86 (12)
O1—C6—C5102.27 (11)C9—N1—C7120.22 (12)
C7—C6—C5105.82 (12)C6—O1—C397.27 (10)
C1—C6—C5110.27 (12)
C6—C1—C2—C30.64 (15)O1—C6—C7—N185.18 (13)
Br1—C1—C2—C3118.41 (11)C1—C6—C7—N1152.93 (13)
C6—C1—C2—Br2A133.9 (3)C5—C6—C7—N125.51 (14)
Br1—C1—C2—Br2A108.3 (3)C6—C5—C8—O2164.98 (15)
C6—C1—C2—Br2124.51 (12)C4—C5—C8—O252.9 (2)
Br1—C1—C2—Br2117.72 (11)C6—C5—C8—N116.51 (15)
C1—C2—C3—O135.54 (14)C4—C5—C8—N1128.64 (14)
Br2A—C2—C3—O1168.9 (3)C14—C9—C10—C110.3 (2)
Br2—C2—C3—O1157.45 (12)N1—C9—C10—C11179.79 (15)
C1—C2—C3—C15153.36 (14)C9—C10—C11—C120.1 (3)
Br2A—C2—C3—C1573.3 (3)C10—C11—C12—C130.4 (3)
Br2—C2—C3—C1584.74 (17)C11—C12—C13—C140.3 (3)
C1—C2—C3—C470.91 (15)C12—C13—C14—C90.1 (3)
Br2A—C2—C3—C462.4 (3)C10—C9—C14—C130.4 (2)
Br2—C2—C3—C450.99 (17)N1—C9—C14—C13179.71 (15)
O1—C3—C4—C536.84 (14)O2—C8—N1—C93.2 (3)
C15—C3—C4—C5157.42 (14)C5—C8—N1—C9175.27 (13)
C2—C3—C4—C567.22 (15)O2—C8—N1—C7179.05 (15)
C3—C4—C5—C8115.57 (14)C5—C8—N1—C70.57 (17)
C3—C4—C5—C63.44 (14)C10—C9—N1—C8161.81 (15)
C2—C1—C6—O134.97 (13)C14—C9—N1—C818.1 (2)
Br1—C1—C6—O182.31 (11)C10—C9—N1—C713.8 (2)
C2—C1—C6—C7161.36 (13)C14—C9—N1—C7166.34 (14)
Br1—C1—C6—C744.08 (16)C6—C7—N1—C815.92 (16)
C2—C1—C6—C573.18 (14)C6—C7—N1—C9167.93 (12)
Br1—C1—C6—C5169.54 (10)C7—C6—O1—C3167.25 (12)
C8—C5—C6—O191.53 (13)C1—C6—O1—C359.84 (12)
C4—C5—C6—O130.94 (14)C5—C6—O1—C354.35 (13)
C8—C5—C6—C725.94 (15)C15—C3—O1—C6178.76 (13)
C4—C5—C6—C7148.41 (12)C4—C3—O1—C657.05 (12)
C8—C5—C6—C1160.39 (12)C2—C3—O1—C657.57 (12)
C4—C5—C6—C177.14 (14)
Hydrogen-bond geometry (Å, º) top
Cg5 is the centroid of the C9–C14 ring.
D—H···AD—HH···AD···AD—H···A
C4—H4A···Br20.972.793.2838 (17)113
C13—H13···O2i0.932.583.223 (2)127
C14—H14···O20.932.302.884 (2)120
C5—H5···Cg5ii0.982.493.4195 (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 top
ContactDistanceSymmetry operation
H7A···H142.56-1 + x, y, z
Br1···Br13.4852 (3)-x, -y, 1 - z
H15C···H102.531 - x, -y, 1 - z
H15B···H112.40x, y, -1 + z
Br2A···H123.13-1 + x, y, -1 + z
H5···C142.831 - x, 1 - y, 1 - z
H13···O22.582 - x, 1 - y, 1 - z
Percentage contributions of interatomic contacts to the Hirshfeld surface for the title compound top
ContactPercentage contribution
H···H43.0
Br···H/H···Br21.1
C···H/H···C12.4
O···H/H···O11.9
Br···C/C···Br3.5
Br···Br2.9
Br···O/O···Br2.5
Br···N/N···Br1.1
C···C0.5
C···N/N···C0.5
C···O/O···C0.3
N···O/O···N0.1
N···N0.1
 

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