Syntheses and crystal structures of the anhydride 4-oxa­tetra­cyclo­[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione and the related imide 4-(4-bromo­phen­yl)-4-aza­tetra­cyclo­[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione

The Diels–Alder cyclo­addition of cyclo­hepta­triene and maleic anhydride produces the title carb­oxy­lic anhydride; reaction of this anhydride with 4-bromo­phenyl­aniline forms the corresponding tetra­cyclic imide. The anhydride features C—H...O hydrogen bonds in the solid state, while the imide also features C—H...O hydrogen bonds as well as C—H...π and lone pair–π inter­actions.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 173 K
• R factor = 0.045
• wR factor = 0.116
• Data-to-parameter ratio = 13.3

Structure: II

• Single-crystal X-ray study
• T = 173 K
• R factor = 0.027
• wR factor = 0.072
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3       ..O1       .       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9       ..O3       .       2.73 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         24 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT432_ALERT_2_G Short Inter X...Y Contact  O1       ..C2A              2.93 Ang.
                                                 1-x,1-y,-z  =      3_665 Check
PLAT793_ALERT_4_G Model has Chirality at C3          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C3A         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C4A         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C5          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C5A         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C8          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C8A         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C9          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C9A         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C10         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C10A        (Centro SPGR)          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         25 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  16 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
  15 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: II


Alert level C
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........  <I>CG</I> Check

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT793_ALERT_4_G Model has Chirality at C3          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C5          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C8          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C9          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C10         (Centro SPGR)          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

   1 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
   7 ALERT type 4 Improvement, methodology, query or suggestion
   1 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

For both structures, data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009; Bourhis et al., 2015); software used to prepare material for publication: CrystalMaker (Palmer, 2007).

4-Oxatetracyclo[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione (I)

Crystal data

C11H10O3	F(000) = 800
Mr = 190.19	Dx = 1.464 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 11.3538 (3) Å	Cell parameters from 8934 reflections
b = 7.4062 (2) Å	θ = 3.9–72.4°
c = 20.5398 (5) Å	µ = 0.88 mm^−1
β = 92.6226 (15)°	T = 173 K
V = 1725.35 (8) Å^3	Chunk, colourless
Z = 8	0.53 × 0.32 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer	3070 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.028
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 72.4°, θmin = 4.3°
Tmin = 0.675, Tmax = 0.754	h = −14→13
13466 measured reflections	k = −9→9
3353 independent reflections	l = −25→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0673P)^2 + 0.5724P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3353 reflections	Δρmax = 0.22 e Å^−3
253 parameters	Δρmin = −0.40 e Å^−3
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.92952 (11)	0.22515 (15)	0.01539 (5)	0.0378 (3)
O2	0.91944 (10)	0.21601 (15)	0.23113 (5)	0.0354 (3)
O3	0.92868 (9)	0.18344 (13)	0.12312 (5)	0.0287 (2)
C1	0.92625 (12)	0.29232 (19)	0.06814 (7)	0.0249 (3)
C2	0.92145 (12)	0.28818 (19)	0.17941 (7)	0.0243 (3)
C3	0.92092 (11)	0.48779 (18)	0.08716 (6)	0.0212 (3)
H3	0.9931	0.5521	0.0734	0.025*
C4	0.91806 (11)	0.48510 (18)	0.16185 (6)	0.0206 (3)
H4	0.9892	0.5477	0.1814	0.025*
C5	0.80361 (12)	0.57992 (19)	0.18403 (6)	0.0240 (3)
H5	0.7976	0.5761	0.2324	0.029*
C6	0.70138 (12)	0.4864 (2)	0.14922 (7)	0.0284 (3)
H6	0.6400	0.4300	0.1717	0.034*
C7	0.70364 (12)	0.4889 (2)	0.08459 (8)	0.0288 (3)
H7	0.6438	0.4348	0.0573	0.035*
C8	0.80824 (12)	0.58391 (19)	0.05799 (6)	0.0245 (3)
H8	0.8054	0.5833	0.0093	0.029*
C9	0.81906 (12)	0.77608 (19)	0.08545 (7)	0.0259 (3)
H9	0.8782	0.8575	0.0659	0.031*
C10	0.81589 (12)	0.77348 (19)	0.15890 (7)	0.0255 (3)
H10	0.8732	0.8536	0.1835	0.031*
C11	0.71901 (13)	0.8646 (2)	0.11912 (8)	0.0317 (3)
H11C	0.7163	0.9982	0.1197	0.038*
H11D	0.6410	0.8046	0.1159	0.038*
O1A	0.45014 (10)	0.77462 (14)	0.02985 (5)	0.0328 (3)
O2A	0.12278 (10)	0.77025 (15)	0.13936 (6)	0.0386 (3)
O3A	0.28206 (9)	0.73501 (13)	0.08039 (5)	0.0313 (3)
C1A	0.36811 (12)	0.84253 (19)	0.05447 (6)	0.0241 (3)
C2A	0.19782 (12)	0.8398 (2)	0.10974 (7)	0.0270 (3)
C3A	0.34016 (11)	1.03897 (17)	0.06434 (6)	0.0206 (3)
H3A	0.3307	1.1025	0.0215	0.025*
C4A	0.22267 (11)	1.03737 (18)	0.09904 (6)	0.0219 (3)
H4A	0.1585	1.0939	0.0710	0.026*
C5A	0.23788 (12)	1.13775 (19)	0.16575 (6)	0.0239 (3)
H5A	0.1634	1.1373	0.1899	0.029*
C6A	0.33646 (12)	1.04165 (19)	0.20315 (6)	0.0254 (3)
H6A	0.3267	0.9881	0.2446	0.031*
C7A	0.43832 (12)	1.03759 (19)	0.17356 (6)	0.0240 (3)
H7A	0.5066	0.9791	0.1919	0.029*
C8A	0.43686 (11)	1.13289 (18)	0.10893 (6)	0.0216 (3)
H8A	0.5158	1.1289	0.0893	0.026*
C9A	0.39235 (12)	1.32691 (19)	0.11555 (7)	0.0250 (3)
H9A	0.4001	1.4080	0.0771	0.030*
C10A	0.27558 (12)	1.32973 (19)	0.14820 (7)	0.0260 (3)
H10A	0.2131	1.4120	0.1293	0.031*
C11A	0.38257 (13)	1.4167 (2)	0.18102 (7)	0.0307 (3)
H11A	0.4195	1.3554	0.2196	0.037*
H11B	0.3854	1.5503	0.1826	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0524 (7)	0.0336 (6)	0.0279 (6)	0.0065 (5)	0.0060 (5)	−0.0079 (4)
O2	0.0469 (7)	0.0310 (6)	0.0285 (5)	−0.0024 (5)	0.0018 (5)	0.0078 (4)
O3	0.0367 (6)	0.0208 (5)	0.0286 (5)	0.0005 (4)	0.0026 (4)	−0.0004 (4)
C1	0.0235 (6)	0.0260 (7)	0.0255 (7)	0.0018 (5)	0.0032 (5)	−0.0010 (5)
C2	0.0223 (6)	0.0261 (7)	0.0246 (7)	−0.0028 (5)	0.0009 (5)	0.0001 (5)
C3	0.0198 (6)	0.0226 (6)	0.0212 (6)	−0.0012 (5)	0.0027 (5)	−0.0005 (5)
C4	0.0186 (6)	0.0226 (6)	0.0205 (6)	−0.0031 (5)	0.0007 (5)	−0.0005 (5)
C5	0.0220 (6)	0.0265 (7)	0.0238 (6)	−0.0006 (5)	0.0050 (5)	−0.0031 (5)
C6	0.0192 (6)	0.0274 (7)	0.0391 (8)	−0.0028 (5)	0.0066 (6)	−0.0035 (6)
C7	0.0210 (7)	0.0274 (7)	0.0375 (8)	−0.0006 (5)	−0.0039 (6)	−0.0077 (6)
C8	0.0253 (7)	0.0258 (7)	0.0220 (6)	0.0028 (5)	−0.0025 (5)	−0.0014 (5)
C9	0.0263 (7)	0.0232 (7)	0.0281 (7)	0.0024 (5)	−0.0008 (5)	0.0013 (5)
C10	0.0245 (7)	0.0241 (7)	0.0279 (7)	0.0000 (5)	0.0004 (5)	−0.0051 (5)
C11	0.0281 (7)	0.0269 (7)	0.0398 (8)	0.0063 (6)	−0.0011 (6)	−0.0046 (6)
O1A	0.0345 (6)	0.0312 (5)	0.0329 (5)	0.0046 (4)	0.0041 (4)	−0.0083 (4)
O2A	0.0344 (6)	0.0365 (6)	0.0454 (7)	−0.0156 (5)	0.0066 (5)	0.0019 (5)
O3A	0.0321 (6)	0.0218 (5)	0.0399 (6)	−0.0027 (4)	0.0022 (4)	−0.0014 (4)
C1A	0.0268 (7)	0.0251 (7)	0.0201 (6)	−0.0015 (5)	−0.0031 (5)	−0.0024 (5)
C2A	0.0242 (7)	0.0278 (7)	0.0287 (7)	−0.0053 (5)	−0.0024 (5)	−0.0007 (6)
C3A	0.0226 (6)	0.0217 (6)	0.0175 (6)	0.0003 (5)	0.0003 (5)	0.0014 (5)
C4A	0.0188 (6)	0.0245 (7)	0.0221 (6)	−0.0008 (5)	−0.0009 (5)	0.0019 (5)
C5A	0.0211 (6)	0.0275 (7)	0.0236 (6)	−0.0012 (5)	0.0050 (5)	−0.0008 (5)
C6A	0.0284 (7)	0.0299 (7)	0.0180 (6)	−0.0031 (6)	0.0009 (5)	0.0014 (5)
C7A	0.0237 (6)	0.0266 (7)	0.0215 (6)	0.0004 (5)	−0.0031 (5)	−0.0011 (5)
C8A	0.0194 (6)	0.0239 (7)	0.0218 (6)	−0.0021 (5)	0.0031 (5)	−0.0018 (5)
C9A	0.0260 (7)	0.0225 (7)	0.0267 (7)	−0.0031 (5)	0.0046 (5)	−0.0005 (5)
C10A	0.0261 (7)	0.0239 (7)	0.0282 (7)	0.0029 (5)	0.0043 (5)	−0.0021 (5)
C11A	0.0328 (8)	0.0265 (7)	0.0330 (8)	−0.0023 (6)	0.0037 (6)	−0.0070 (6)

Geometric parameters (Å, º)

O1—C1	1.1943 (18)	O1A—C1A	1.1913 (17)
O2—C2	1.1904 (17)	O2A—C2A	1.1871 (18)
O3—C1	1.3868 (17)	O3A—C1A	1.3855 (17)
O3—C2	1.3978 (16)	O3A—C2A	1.3905 (18)
C1—C3	1.5014 (18)	C1A—C3A	1.5048 (18)
C2—C4	1.5024 (18)	C2A—C4A	1.5080 (19)
C3—H3	1.0000	C3A—H3A	1.0000
C3—C4	1.5360 (17)	C3A—C4A	1.5409 (17)
C3—C8	1.5596 (18)	C3A—C8A	1.5607 (17)
C4—H4	1.0000	C4A—H4A	1.0000
C4—C5	1.5631 (17)	C4A—C5A	1.5616 (18)
C5—H5	1.0000	C5A—H5A	1.0000
C5—C6	1.5040 (19)	C5A—C6A	1.5068 (19)
C5—C10	1.5321 (19)	C5A—C10A	1.5326 (19)
C6—H6	0.9500	C6A—H6A	0.9500
C6—C7	1.329 (2)	C6A—C7A	1.3312 (19)
C7—H7	0.9500	C7A—H7A	0.9500
C7—C8	1.504 (2)	C7A—C8A	1.5028 (18)
C8—H8	1.0000	C8A—H8A	1.0000
C8—C9	1.5337 (19)	C8A—C9A	1.5313 (19)
C9—H9	1.0000	C9A—H9A	1.0000
C9—C10	1.5110 (19)	C9A—C10A	1.5131 (18)
C9—C11	1.5066 (19)	C9A—C11A	1.5091 (19)
C10—H10	1.0000	C10A—H10A	1.0000
C10—C11	1.500 (2)	C10A—C11A	1.507 (2)
C11—H11C	0.9900	C11A—H11A	0.9900
C11—H11D	0.9900	C11A—H11B	0.9900
C1—O3—C2	110.55 (11)	C1A—O3A—C2A	110.90 (11)
O1—C1—O3	119.75 (13)	O1A—C1A—O3A	119.95 (13)
O1—C1—C3	129.86 (13)	O1A—C1A—C3A	129.73 (13)
O3—C1—C3	110.39 (11)	O3A—C1A—C3A	110.31 (11)
O2—C2—O3	119.55 (13)	O2A—C2A—O3A	120.26 (14)
O2—C2—C4	130.45 (13)	O2A—C2A—C4A	129.74 (14)
O3—C2—C4	110.00 (11)	O3A—C2A—C4A	109.97 (11)
C1—C3—H3	110.1	C1A—C3A—H3A	110.6
C1—C3—C4	104.49 (10)	C1A—C3A—C4A	104.31 (11)
C1—C3—C8	112.48 (11)	C1A—C3A—C8A	111.28 (11)
C4—C3—H3	110.1	C4A—C3A—H3A	110.6
C4—C3—C8	109.58 (10)	C4A—C3A—C8A	109.43 (10)
C8—C3—H3	110.1	C8A—C3A—H3A	110.6
C2—C4—C3	104.53 (10)	C2A—C4A—C3A	104.27 (11)
C2—C4—H4	110.0	C2A—C4A—H4A	110.7
C2—C4—C5	112.25 (11)	C2A—C4A—C5A	110.36 (11)
C3—C4—H4	110.0	C3A—C4A—H4A	110.7
C3—C4—C5	109.95 (10)	C3A—C4A—C5A	109.80 (10)
C5—C4—H4	110.0	C5A—C4A—H4A	110.7
C4—C5—H5	111.9	C4A—C5A—H5A	111.8
C6—C5—C4	106.76 (11)	C6A—C5A—C4A	105.79 (10)
C6—C5—H5	111.9	C6A—C5A—H5A	111.8
C6—C5—C10	110.54 (12)	C6A—C5A—C10A	110.44 (11)
C10—C5—C4	103.44 (10)	C10A—C5A—C4A	104.84 (10)
C10—C5—H5	111.9	C10A—C5A—H5A	111.8
C5—C6—H6	122.6	C5A—C6A—H6A	122.6
C7—C6—C5	114.75 (12)	C7A—C6A—C5A	114.74 (12)
C7—C6—H6	122.6	C7A—C6A—H6A	122.6
C6—C7—H7	122.6	C6A—C7A—H7A	122.6
C6—C7—C8	114.89 (12)	C6A—C7A—C8A	114.71 (12)
C8—C7—H7	122.6	C8A—C7A—H7A	122.6
C3—C8—H8	111.8	C3A—C8A—H8A	111.7
C7—C8—C3	107.11 (11)	C7A—C8A—C3A	106.74 (10)
C7—C8—H8	111.8	C7A—C8A—H8A	111.7
C7—C8—C9	110.60 (11)	C7A—C8A—C9A	110.65 (11)
C9—C8—C3	103.41 (10)	C9A—C8A—C3A	104.13 (10)
C9—C8—H8	111.8	C9A—C8A—H8A	111.7
C8—C9—H9	117.1	C8A—C9A—H9A	116.9
C10—C9—C8	110.50 (11)	C10A—C9A—C8A	110.59 (11)
C10—C9—H9	117.1	C10A—C9A—H9A	116.9
C11—C9—C8	121.54 (12)	C11A—C9A—C8A	122.06 (12)
C11—C9—H9	117.1	C11A—C9A—H9A	116.9
C11—C9—C10	59.62 (9)	C11A—C9A—C10A	59.82 (9)
C5—C10—H10	116.9	C5A—C10A—H10A	117.1
C9—C10—C5	110.79 (11)	C9A—C10A—C5A	110.56 (11)
C9—C10—H10	116.9	C9A—C10A—H10A	117.1
C11—C10—C5	121.90 (12)	C11A—C10A—C5A	121.31 (12)
C11—C10—C9	60.05 (9)	C11A—C10A—C9A	59.96 (9)
C11—C10—H10	116.9	C11A—C10A—H10A	117.1
C9—C11—H11C	117.7	C9A—C11A—H11A	117.7
C9—C11—H11D	117.7	C9A—C11A—H11B	117.7
C10—C11—C9	60.33 (9)	C10A—C11A—C9A	60.22 (9)
C10—C11—H11C	117.7	C10A—C11A—H11A	117.7
C10—C11—H11D	117.7	C10A—C11A—H11B	117.7
H11C—C11—H11D	114.9	H11A—C11A—H11B	114.9

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1^i	1.00	2.64	3.4882 (17)	143
C3—H3···O2A^ii	1.00	2.54	3.2487 (17)	128
C4—H4···O2A^ii	1.00	2.43	3.1897 (16)	133
C7—H7···O1A^iii	0.95	2.56	3.4652 (18)	159
C8A—H8A···O1A^iv	1.00	2.59	3.2521 (17)	123
C9—H9···O3^v	1.00	2.73	3.3409 (17)	119

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

4-(4-Bromophenyl)-4-azatetracyclo[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione (II)

Crystal data

C17H14BrNO2	F(000) = 696
Mr = 344.20	Dx = 1.619 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 12.49907 (16) Å	Cell parameters from 9902 reflections
b = 6.41302 (8) Å	θ = 4.7–70.1°
c = 17.8772 (2) Å	µ = 4.00 mm^−1
β = 99.8083 (6)°	T = 173 K
V = 1412.04 (3) Å^3	Needle, colourless
Z = 4	0.42 × 0.12 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer	2441 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.039
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θmax = 70.2°, θmin = 4.0°
Tmin = 0.578, Tmax = 0.753	h = −15→15
23789 measured reflections	k = −7→7
2683 independent reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.072	w = 1/[σ^2(Fo^2) + (0.033P)^2 + 1.1866P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.003
2683 reflections	Δρmax = 0.56 e Å^−3
190 parameters	Δρmin = −0.48 e Å^−3
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.63472 (2)	−0.24792 (4)	0.56752 (2)	0.03728 (10)
O1	0.18672 (12)	−0.1467 (3)	0.72460 (9)	0.0360 (4)
O2	0.19184 (11)	0.3903 (2)	0.55825 (8)	0.0307 (3)
N1	0.21210 (12)	0.1061 (2)	0.63812 (8)	0.0204 (3)
C1	0.16094 (14)	0.0182 (3)	0.69397 (10)	0.0237 (4)
C2	0.16488 (15)	0.2941 (3)	0.61018 (11)	0.0218 (4)
C3	0.07071 (14)	0.1617 (3)	0.70770 (10)	0.0233 (4)
H3	0.0846	0.2102	0.7616	0.028*
C4	0.07607 (14)	0.3487 (3)	0.65452 (10)	0.0229 (4)
H4	0.0962	0.4777	0.6851	0.028*
C5	−0.03628 (15)	0.3789 (3)	0.60269 (11)	0.0257 (4)
H5	−0.0355	0.4979	0.5667	0.031*
C6	−0.06246 (15)	0.1766 (3)	0.56169 (11)	0.0288 (4)
H6	−0.0753	0.1670	0.5079	0.035*
C7	−0.06639 (15)	0.0122 (3)	0.60590 (12)	0.0280 (4)
H7	−0.0819	−0.1243	0.5864	0.034*
C8	−0.04426 (14)	0.0588 (3)	0.68951 (11)	0.0258 (4)
H8	−0.0490	−0.0694	0.7206	0.031*
C9	−0.12081 (16)	0.2311 (3)	0.70832 (12)	0.0285 (4)
H9	−0.1212	0.2589	0.7633	0.034*
C10	−0.11491 (16)	0.4179 (3)	0.65832 (12)	0.0300 (4)
H10	−0.1116	0.5579	0.6832	0.036*
C11	−0.21970 (16)	0.2988 (4)	0.65312 (14)	0.0348 (5)
H11A	−0.2427	0.2114	0.6076	0.042*
H11B	−0.2797	0.3652	0.6741	0.042*
C12	0.31028 (14)	0.0235 (3)	0.61886 (10)	0.0209 (4)
C13	0.40447 (15)	0.1405 (3)	0.63508 (11)	0.0262 (4)
H13	0.4030	0.2752	0.6569	0.031*
C14	0.50106 (16)	0.0594 (3)	0.61918 (11)	0.0296 (4)
H14	0.5662	0.1383	0.6299	0.035*
C15	0.50157 (15)	−0.1369 (3)	0.58771 (10)	0.0254 (4)
C16	0.40808 (18)	−0.2541 (3)	0.57108 (11)	0.0284 (4)
H16	0.4098	−0.3887	0.5491	0.034*
C17	0.31120 (15)	−0.1728 (3)	0.58690 (11)	0.0253 (4)
H17	0.2461	−0.2516	0.5758	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.03088 (14)	0.04690 (17)	0.03609 (15)	0.01410 (9)	0.01146 (10)	−0.00083 (10)
O1	0.0294 (7)	0.0422 (9)	0.0382 (8)	0.0087 (6)	0.0107 (6)	0.0211 (7)
O2	0.0312 (7)	0.0263 (7)	0.0371 (8)	0.0002 (6)	0.0131 (6)	0.0095 (6)
N1	0.0175 (7)	0.0233 (8)	0.0205 (7)	−0.0015 (6)	0.0031 (6)	0.0013 (6)
C1	0.0184 (8)	0.0322 (10)	0.0197 (8)	−0.0015 (7)	0.0008 (7)	0.0046 (8)
C2	0.0201 (8)	0.0194 (8)	0.0252 (9)	−0.0045 (7)	0.0019 (7)	−0.0007 (7)
C3	0.0197 (8)	0.0319 (10)	0.0184 (8)	−0.0016 (7)	0.0034 (7)	0.0010 (8)
C4	0.0221 (9)	0.0213 (9)	0.0257 (9)	−0.0033 (7)	0.0049 (7)	−0.0033 (7)
C5	0.0235 (9)	0.0243 (9)	0.0295 (9)	0.0043 (7)	0.0049 (7)	0.0054 (8)
C6	0.0211 (9)	0.0397 (11)	0.0239 (9)	0.0038 (8)	−0.0010 (7)	−0.0059 (9)
C7	0.0180 (8)	0.0260 (10)	0.0394 (11)	−0.0015 (7)	0.0028 (8)	−0.0097 (9)
C8	0.0191 (9)	0.0276 (10)	0.0315 (10)	−0.0018 (7)	0.0063 (7)	0.0049 (8)
C9	0.0210 (9)	0.0346 (11)	0.0312 (10)	−0.0008 (8)	0.0083 (8)	−0.0033 (8)
C10	0.0241 (9)	0.0272 (10)	0.0400 (11)	0.0023 (8)	0.0093 (8)	−0.0043 (9)
C11	0.0203 (10)	0.0382 (11)	0.0465 (12)	0.0036 (9)	0.0074 (9)	−0.0021 (10)
C12	0.0201 (8)	0.0247 (9)	0.0180 (8)	0.0000 (7)	0.0037 (7)	0.0022 (7)
C13	0.0248 (9)	0.0266 (10)	0.0284 (9)	−0.0035 (8)	0.0080 (7)	−0.0061 (8)
C14	0.0215 (9)	0.0362 (11)	0.0322 (10)	−0.0042 (8)	0.0082 (8)	−0.0057 (9)
C15	0.0245 (9)	0.0315 (10)	0.0213 (8)	0.0084 (8)	0.0071 (7)	0.0025 (8)
C16	0.0358 (11)	0.0239 (10)	0.0253 (9)	0.0045 (8)	0.0042 (8)	−0.0017 (8)
C17	0.0244 (9)	0.0246 (9)	0.0259 (9)	−0.0023 (7)	0.0011 (7)	0.0013 (8)

Geometric parameters (Å, º)

Br1—C15	1.9004 (18)	C8—H8	1.0000
O1—C1	1.210 (2)	C8—C9	1.536 (3)
O2—C2	1.209 (2)	C9—H9	1.0000
N1—C1	1.393 (2)	C9—C10	1.504 (3)
N1—C2	1.397 (2)	C9—C11	1.508 (3)
N1—C12	1.432 (2)	C10—H10	1.0000
C1—C3	1.508 (3)	C10—C11	1.506 (3)
C2—C4	1.511 (2)	C11—H11A	0.9900
C3—H3	1.0000	C11—H11B	0.9900
C3—C4	1.539 (3)	C12—C13	1.384 (3)
C3—C8	1.564 (2)	C12—C17	1.383 (3)
C4—H4	1.0000	C13—H13	0.9500
C4—C5	1.557 (3)	C13—C14	1.388 (3)
C5—H5	1.0000	C14—H14	0.9500
C5—C6	1.499 (3)	C14—C15	1.379 (3)
C5—C10	1.533 (3)	C15—C16	1.379 (3)
C6—H6	0.9500	C16—H16	0.9500
C6—C7	1.324 (3)	C16—C17	1.391 (3)
C7—H7	0.9500	C17—H17	0.9500
C7—C8	1.503 (3)
C1—N1—C2	112.82 (15)	C9—C8—H8	111.8
C1—N1—C12	122.65 (15)	C8—C9—H9	116.8
C2—N1—C12	124.12 (15)	C10—C9—C8	110.33 (16)
O1—C1—N1	123.98 (17)	C10—C9—H9	116.8
O1—C1—C3	127.52 (17)	C10—C9—C11	59.97 (14)
N1—C1—C3	108.50 (15)	C11—C9—C8	122.38 (18)
O2—C2—N1	123.97 (17)	C11—C9—H9	116.8
O2—C2—C4	127.59 (17)	C5—C10—H10	116.9
N1—C2—C4	108.43 (15)	C9—C10—C5	110.92 (16)
C1—C3—H3	109.6	C9—C10—H10	116.9
C1—C3—C4	105.22 (14)	C9—C10—C11	60.14 (14)
C1—C3—C8	113.26 (16)	C11—C10—C5	121.61 (18)
C4—C3—H3	109.6	C11—C10—H10	116.9
C4—C3—C8	109.59 (15)	C9—C11—H11A	117.8
C8—C3—H3	109.6	C9—C11—H11B	117.8
C2—C4—C3	104.86 (15)	C10—C11—C9	59.89 (13)
C2—C4—H4	109.9	C10—C11—H11A	117.8
C2—C4—C5	112.66 (15)	C10—C11—H11B	117.8
C3—C4—H4	109.9	H11A—C11—H11B	114.9
C3—C4—C5	109.55 (14)	C13—C12—N1	118.82 (16)
C5—C4—H4	109.9	C17—C12—N1	120.27 (16)
C4—C5—H5	111.8	C17—C12—C13	120.88 (17)
C6—C5—C4	106.45 (15)	C12—C13—H13	120.2
C6—C5—H5	111.8	C12—C13—C14	119.50 (18)
C6—C5—C10	110.37 (16)	C14—C13—H13	120.2
C10—C5—C4	104.30 (15)	C13—C14—H14	120.3
C10—C5—H5	111.8	C15—C14—C13	119.34 (18)
C5—C6—H6	122.4	C15—C14—H14	120.3
C7—C6—C5	115.13 (17)	C14—C15—Br1	118.97 (15)
C7—C6—H6	122.4	C16—C15—Br1	119.49 (15)
C6—C7—H7	122.7	C16—C15—C14	121.54 (18)
C6—C7—C8	114.59 (18)	C15—C16—H16	120.4
C8—C7—H7	122.7	C15—C16—C17	119.14 (18)
C3—C8—H8	111.8	C17—C16—H16	120.4
C7—C8—C3	107.32 (15)	C12—C17—C16	119.60 (18)
C7—C8—H8	111.8	C12—C17—H17	120.2
C7—C8—C9	110.18 (16)	C16—C17—H17	120.2
C9—C8—C3	103.63 (15)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O2^i	0.95	2.40	3.175 (2)	139
C3—H3···Cg1^ii	1.00	2.83	3.801 (2)	165

Symmetry codes: (i) x, y−1, z; (ii) −x+1/2, y+1/2, −z+3/2.