Crystal structure and Hirshfeld surface analysis of 2-benzyl-4,5-di­bromo-2,3,3a,4,5,6,7,7a-octa­hydro-3a,6-ep­oxy-1H-isoindol-1-one

In the crystal, mol­ecules are linked by weak C—H...O hydrogen bonds, forming sheets lying parallel to the (002) plane. These sheets are connected only by weak van der Waals inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.043
• wR factor = 0.091
• Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A      ..O2A      .       2.64 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7BB     ..O2B      .       2.64 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.842 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1A             96.2 Degree
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1B             96.4 Degree
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         12 Note
PLAT793_ALERT_4_G Model has Chirality at C1A         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C1B         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C2A         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C2B         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C3A         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C3B         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C5A         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C5B         (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C6A         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C6B         (Centro SPGR)          S Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          4 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        103 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         10 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
  14 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

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) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: PLATON (Spek, 2020).

2-Benzyl-4,5-dibromo-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one

Crystal data

C15H15Br2NO2	F(000) = 1584
Mr = 401.10	Dx = 1.777 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 17.4839 (5) Å	Cell parameters from 5179 reflections
b = 8.2993 (3) Å	θ = 2.7–22.8°
c = 21.5120 (7) Å	µ = 5.41 mm^−1
β = 106.115 (2)°	T = 296 K
V = 2998.83 (17) Å^3	Hexagonal prisms, colourless
Z = 8	0.14 × 0.13 × 0.13 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer	3997 reflections with I > 2σ(I)
ω– and φ–scans	Rint = 0.053
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 27.8°, θmin = 2.7°
Tmin = 0.224, Tmax = 0.294	h = −22→22
32806 measured reflections	k = −10→10
6995 independent reflections	l = −28→27

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0333P)^2 + 1.282P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.091	(Δ/σ)max = 0.001
S = 1.02	Δρmax = 0.83 e Å^−3
6995 reflections	Δρmin = −0.65 e Å^−3
362 parameters	Extinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.00111 (12)
Primary atom site location: inferred from neighbouring sites

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
C1A	0.8852 (2)	0.3745 (4)	0.38724 (16)	0.0370 (9)
H1A	0.900973	0.406568	0.348719	0.044*
C2A	0.9420 (2)	0.2461 (5)	0.42647 (17)	0.0449 (10)
H2A	0.959259	0.280858	0.471765	0.054*
C3A	0.8874 (2)	0.0992 (5)	0.42168 (18)	0.0482 (10)
H3A	0.907172	0.020343	0.456328	0.058*
C4A	0.8625 (2)	0.0245 (5)	0.35457 (19)	0.0519 (11)
H4AA	0.833459	−0.075272	0.354065	0.062*
H4AB	0.907972	0.004926	0.338033	0.062*
C5A	0.8091 (2)	0.1574 (4)	0.31692 (16)	0.0362 (9)
H5A	0.831483	0.203675	0.283872	0.043*
C6A	0.80785 (19)	0.2812 (4)	0.36906 (15)	0.0309 (8)
C7A	0.72741 (19)	0.3587 (4)	0.34938 (16)	0.0373 (9)
H7AA	0.707948	0.380283	0.386626	0.045*
H7AB	0.728396	0.458539	0.326150	0.045*
C8A	0.7213 (2)	0.1203 (5)	0.28926 (16)	0.0413 (9)
C9A	0.5932 (2)	0.2502 (5)	0.28436 (17)	0.0511 (11)
H9AA	0.574028	0.171921	0.250087	0.061*
H9AB	0.579798	0.356414	0.265650	0.061*
C10A	0.5498 (2)	0.2245 (4)	0.33480 (17)	0.0381 (9)
C11A	0.4700 (2)	0.2679 (5)	0.31950 (19)	0.0495 (10)
H11A	0.445253	0.311234	0.279045	0.059*
C12A	0.4276 (2)	0.2472 (5)	0.3638 (2)	0.0607 (12)
H12A	0.374225	0.276410	0.353302	0.073*
C13A	0.4637 (3)	0.1837 (5)	0.4234 (2)	0.0606 (12)
H13A	0.434686	0.168605	0.453196	0.073*
C14A	0.5425 (3)	0.1423 (5)	0.4392 (2)	0.0573 (11)
H14A	0.567212	0.100717	0.479959	0.069*
C15A	0.5855 (2)	0.1619 (5)	0.39485 (17)	0.0454 (10)
H15A	0.638886	0.132644	0.405694	0.055*
N1A	0.67922 (17)	0.2373 (4)	0.30754 (13)	0.0413 (8)
O1A	0.81551 (14)	0.1790 (3)	0.42508 (10)	0.0424 (6)
O2A	0.69344 (17)	0.0056 (3)	0.25485 (13)	0.0602 (8)
Br1A	0.87859 (2)	0.56161 (5)	0.44107 (2)	0.05631 (15)
Br2A	1.03562 (3)	0.20912 (6)	0.39717 (3)	0.07454 (18)
C1B	0.7908 (2)	0.1347 (4)	0.61250 (16)	0.0372 (9)
H1B	0.829984	0.094825	0.651364	0.045*
C2B	0.8272 (2)	0.2662 (5)	0.57905 (17)	0.0440 (10)
H2B	0.815399	0.240013	0.532932	0.053*
C3B	0.7797 (2)	0.4175 (5)	0.58646 (19)	0.0520 (11)
H3B	0.780526	0.501711	0.554716	0.062*
C4B	0.7985 (3)	0.4797 (5)	0.6555 (2)	0.0576 (12)
H4BA	0.772113	0.581506	0.657849	0.069*
H4BB	0.855305	0.491715	0.674785	0.069*
C5B	0.7640 (2)	0.3436 (4)	0.68693 (16)	0.0379 (9)
H5B	0.806381	0.287933	0.719270	0.045*
C6B	0.7267 (2)	0.2315 (4)	0.63022 (15)	0.0342 (8)
C7B	0.6560 (2)	0.1563 (5)	0.64522 (17)	0.0435 (9)
H7BA	0.612042	0.144230	0.606419	0.052*
H7BB	0.669218	0.051786	0.665507	0.052*
C8B	0.6947 (2)	0.3797 (5)	0.71379 (18)	0.0454 (10)
C9B	0.5654 (2)	0.2577 (6)	0.71072 (19)	0.0575 (12)
H9BA	0.568277	0.335108	0.745061	0.069*
H9BB	0.564186	0.150991	0.728853	0.069*
C10B	0.4888 (2)	0.2840 (4)	0.65875 (18)	0.0419 (9)
C11B	0.4196 (2)	0.2234 (5)	0.6684 (2)	0.0561 (11)
H11B	0.421680	0.166181	0.705987	0.067*
C12B	0.3474 (3)	0.2465 (6)	0.6231 (3)	0.0698 (14)
H12B	0.301036	0.205823	0.630294	0.084*
C13B	0.3441 (3)	0.3291 (6)	0.5677 (3)	0.0691 (14)
H13B	0.295513	0.343200	0.536779	0.083*
C14B	0.4122 (3)	0.3918 (5)	0.5572 (2)	0.0618 (12)
H14B	0.409600	0.449397	0.519547	0.074*
C15B	0.4852 (2)	0.3686 (5)	0.60312 (19)	0.0509 (10)
H15B	0.531509	0.410312	0.596131	0.061*
N1B	0.63674 (18)	0.2718 (4)	0.68980 (14)	0.0465 (8)
O1B	0.70287 (14)	0.3452 (3)	0.57735 (11)	0.0503 (7)
O2B	0.69187 (17)	0.4868 (4)	0.75178 (14)	0.0648 (8)
Br1B	0.74753 (3)	−0.04142 (6)	0.55333 (2)	0.06418 (16)
Br2B	0.94187 (2)	0.28604 (6)	0.61425 (2)	0.06177 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.037 (2)	0.040 (2)	0.036 (2)	−0.0011 (18)	0.0147 (17)	−0.0043 (17)
C2A	0.038 (2)	0.055 (3)	0.039 (2)	0.0064 (19)	0.0054 (18)	−0.0034 (19)
C3A	0.046 (2)	0.048 (2)	0.048 (2)	0.008 (2)	0.008 (2)	0.013 (2)
C4A	0.052 (3)	0.039 (2)	0.065 (3)	−0.002 (2)	0.017 (2)	−0.010 (2)
C5A	0.037 (2)	0.039 (2)	0.035 (2)	−0.0019 (17)	0.0145 (17)	−0.0052 (17)
C6A	0.0317 (19)	0.037 (2)	0.0262 (18)	0.0007 (17)	0.0116 (15)	0.0010 (16)
C7A	0.034 (2)	0.043 (2)	0.038 (2)	−0.0003 (18)	0.0151 (17)	−0.0061 (18)
C8A	0.047 (2)	0.051 (3)	0.027 (2)	−0.010 (2)	0.0127 (18)	−0.0056 (19)
C9A	0.034 (2)	0.074 (3)	0.039 (2)	−0.003 (2)	0.0010 (18)	0.004 (2)
C10A	0.031 (2)	0.042 (2)	0.039 (2)	−0.0070 (17)	0.0072 (17)	−0.0031 (18)
C11A	0.038 (2)	0.056 (3)	0.051 (2)	−0.004 (2)	0.005 (2)	−0.001 (2)
C12A	0.038 (2)	0.059 (3)	0.088 (4)	−0.004 (2)	0.022 (3)	−0.009 (3)
C13A	0.061 (3)	0.065 (3)	0.068 (3)	−0.016 (3)	0.038 (3)	−0.014 (3)
C14A	0.061 (3)	0.066 (3)	0.045 (3)	−0.011 (2)	0.015 (2)	0.002 (2)
C15A	0.038 (2)	0.055 (3)	0.043 (2)	−0.0004 (19)	0.0104 (19)	0.0004 (19)
N1A	0.0313 (16)	0.058 (2)	0.0347 (17)	−0.0048 (15)	0.0094 (14)	−0.0095 (15)
O1A	0.0450 (15)	0.0525 (16)	0.0315 (14)	−0.0023 (13)	0.0140 (12)	0.0063 (12)
O2A	0.0576 (19)	0.071 (2)	0.0518 (17)	−0.0166 (16)	0.0157 (15)	−0.0287 (15)
Br1A	0.0431 (2)	0.0517 (3)	0.0735 (3)	−0.0083 (2)	0.0150 (2)	−0.0237 (2)
Br2A	0.0425 (3)	0.0729 (3)	0.1129 (4)	0.0071 (2)	0.0293 (3)	−0.0161 (3)
C1B	0.034 (2)	0.045 (2)	0.0293 (19)	−0.0019 (18)	0.0033 (16)	−0.0069 (17)
C2B	0.033 (2)	0.066 (3)	0.032 (2)	−0.0049 (19)	0.0068 (17)	−0.0002 (19)
C3B	0.049 (3)	0.055 (3)	0.052 (3)	0.004 (2)	0.014 (2)	0.019 (2)
C4B	0.057 (3)	0.039 (2)	0.079 (3)	−0.003 (2)	0.021 (2)	−0.007 (2)
C5B	0.0310 (19)	0.045 (2)	0.034 (2)	0.0007 (17)	0.0029 (16)	−0.0066 (17)
C6B	0.0319 (19)	0.041 (2)	0.0261 (19)	0.0007 (17)	0.0029 (15)	0.0007 (16)
C7B	0.031 (2)	0.054 (3)	0.042 (2)	−0.0040 (18)	0.0058 (17)	−0.0103 (19)
C8B	0.039 (2)	0.059 (3)	0.034 (2)	0.008 (2)	0.0017 (18)	−0.004 (2)
C9B	0.041 (2)	0.088 (3)	0.048 (2)	0.003 (2)	0.019 (2)	0.005 (2)
C10B	0.038 (2)	0.041 (2)	0.049 (2)	0.0043 (19)	0.0166 (19)	−0.0047 (19)
C11B	0.046 (3)	0.051 (3)	0.077 (3)	0.005 (2)	0.027 (2)	0.004 (2)
C12B	0.038 (3)	0.062 (3)	0.112 (4)	−0.002 (2)	0.024 (3)	−0.010 (3)
C13B	0.043 (3)	0.068 (3)	0.085 (4)	0.016 (2)	−0.001 (3)	−0.026 (3)
C14B	0.076 (3)	0.054 (3)	0.053 (3)	0.017 (3)	0.014 (3)	−0.005 (2)
C15B	0.046 (3)	0.057 (3)	0.051 (3)	−0.002 (2)	0.016 (2)	−0.004 (2)
N1B	0.0353 (18)	0.069 (2)	0.0368 (18)	−0.0002 (17)	0.0119 (15)	−0.0119 (17)
O1B	0.0382 (15)	0.0691 (19)	0.0386 (15)	0.0098 (14)	0.0022 (12)	0.0128 (13)
O2B	0.0585 (19)	0.078 (2)	0.0557 (18)	0.0063 (16)	0.0126 (15)	−0.0312 (16)
Br1B	0.0532 (3)	0.0681 (3)	0.0736 (3)	−0.0076 (2)	0.0215 (2)	−0.0344 (2)
Br2B	0.0391 (2)	0.0748 (3)	0.0719 (3)	−0.0073 (2)	0.0161 (2)	0.0053 (2)

Geometric parameters (Å, º)

C1A—C6A	1.513 (5)	C1B—C6B	1.512 (5)
C1A—C2A	1.539 (5)	C1B—C2B	1.539 (5)
C1A—Br1A	1.959 (3)	C1B—Br1B	1.948 (3)
C1A—H1A	0.9800	C1B—H1B	0.9800
C2A—C3A	1.534 (5)	C2B—C3B	1.538 (5)
C2A—Br2A	1.935 (4)	C2B—Br2B	1.943 (3)
C2A—H2A	0.9800	C2B—H2B	0.9800
C3A—O1A	1.440 (4)	C3B—O1B	1.434 (4)
C3A—C4A	1.520 (5)	C3B—C4B	1.520 (5)
C3A—H3A	0.9800	C3B—H3B	0.9800
C4A—C5A	1.525 (5)	C4B—C5B	1.524 (5)
C4A—H4AA	0.9700	C4B—H4BA	0.9700
C4A—H4AB	0.9700	C4B—H4BB	0.9700
C5A—C8A	1.516 (5)	C5B—C8B	1.510 (5)
C5A—C6A	1.526 (4)	C5B—C6B	1.529 (4)
C5A—H5A	0.9800	C5B—H5B	0.9800
C6A—O1A	1.449 (4)	C6B—O1B	1.447 (4)
C6A—C7A	1.497 (4)	C6B—C7B	1.497 (5)
C7A—N1A	1.455 (4)	C7B—N1B	1.459 (4)
C7A—H7AA	0.9700	C7B—H7BA	0.9700
C7A—H7AB	0.9700	C7B—H7BB	0.9700
C8A—O2A	1.221 (4)	C8B—O2B	1.218 (4)
C8A—N1A	1.341 (5)	C8B—N1B	1.343 (5)
C9A—N1A	1.452 (4)	C9B—N1B	1.443 (4)
C9A—C10A	1.501 (5)	C9B—C10B	1.504 (5)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C10A—C15A	1.371 (5)	C10B—C15B	1.374 (5)
C10A—C11A	1.389 (5)	C10B—C11B	1.378 (5)
C11A—C12A	1.371 (5)	C11B—C12B	1.377 (6)
C11A—H11A	0.9300	C11B—H11B	0.9300
C12A—C13A	1.368 (6)	C12B—C13B	1.362 (6)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.369 (6)	C13B—C14B	1.374 (6)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.377 (5)	C14B—C15B	1.394 (5)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C6A—C1A—C2A	100.4 (3)	C6B—C1B—C2B	100.0 (3)
C6A—C1A—Br1A	111.3 (2)	C6B—C1B—Br1B	112.5 (2)
C2A—C1A—Br1A	111.1 (2)	C2B—C1B—Br1B	111.3 (2)
C6A—C1A—H1A	111.2	C6B—C1B—H1B	110.9
C2A—C1A—H1A	111.2	C2B—C1B—H1B	110.9
Br1A—C1A—H1A	111.2	Br1B—C1B—H1B	110.9
C3A—C2A—C1A	102.6 (3)	C3B—C2B—C1B	103.0 (3)
C3A—C2A—Br2A	114.8 (3)	C3B—C2B—Br2B	114.8 (3)
C1A—C2A—Br2A	114.0 (2)	C1B—C2B—Br2B	113.2 (2)
C3A—C2A—H2A	108.4	C3B—C2B—H2B	108.5
C1A—C2A—H2A	108.4	C1B—C2B—H2B	108.5
Br2A—C2A—H2A	108.4	Br2B—C2B—H2B	108.5
O1A—C3A—C4A	102.3 (3)	O1B—C3B—C4B	102.4 (3)
O1A—C3A—C2A	99.6 (3)	O1B—C3B—C2B	99.0 (3)
C4A—C3A—C2A	113.4 (3)	C4B—C3B—C2B	113.7 (3)
O1A—C3A—H3A	113.4	O1B—C3B—H3B	113.4
C4A—C3A—H3A	113.4	C4B—C3B—H3B	113.4
C2A—C3A—H3A	113.4	C2B—C3B—H3B	113.4
C3A—C4A—C5A	100.4 (3)	C3B—C4B—C5B	100.2 (3)
C3A—C4A—H4AA	111.7	C3B—C4B—H4BA	111.7
C5A—C4A—H4AA	111.7	C5B—C4B—H4BA	111.7
C3A—C4A—H4AB	111.7	C3B—C4B—H4BB	111.7
C5A—C4A—H4AB	111.7	C5B—C4B—H4BB	111.7
H4AA—C4A—H4AB	109.5	H4BA—C4B—H4BB	109.5
C8A—C5A—C4A	117.8 (3)	C8B—C5B—C4B	118.7 (3)
C8A—C5A—C6A	101.9 (3)	C8B—C5B—C6B	102.4 (3)
C4A—C5A—C6A	103.2 (3)	C4B—C5B—C6B	103.3 (3)
C8A—C5A—H5A	111.1	C8B—C5B—H5B	110.5
C4A—C5A—H5A	111.1	C4B—C5B—H5B	110.5
C6A—C5A—H5A	111.1	C6B—C5B—H5B	110.5
O1A—C6A—C7A	110.5 (3)	O1B—C6B—C7B	111.5 (3)
O1A—C6A—C1A	102.4 (3)	O1B—C6B—C1B	102.7 (3)
C7A—C6A—C1A	123.7 (3)	C7B—C6B—C1B	123.2 (3)
O1A—C6A—C5A	101.6 (3)	O1B—C6B—C5B	101.3 (3)
C7A—C6A—C5A	106.6 (3)	C7B—C6B—C5B	106.1 (3)
C1A—C6A—C5A	109.9 (3)	C1B—C6B—C5B	110.0 (3)
N1A—C7A—C6A	102.4 (3)	N1B—C7B—C6B	102.9 (3)
N1A—C7A—H7AA	111.3	N1B—C7B—H7BA	111.2
C6A—C7A—H7AA	111.3	C6B—C7B—H7BA	111.2
N1A—C7A—H7AB	111.3	N1B—C7B—H7BB	111.2
C6A—C7A—H7AB	111.3	C6B—C7B—H7BB	111.2
H7AA—C7A—H7AB	109.2	H7BA—C7B—H7BB	109.1
O2A—C8A—N1A	125.7 (4)	O2B—C8B—N1B	125.3 (4)
O2A—C8A—C5A	125.9 (3)	O2B—C8B—C5B	126.0 (4)
N1A—C8A—C5A	108.4 (3)	N1B—C8B—C5B	108.7 (3)
N1A—C9A—C10A	115.1 (3)	N1B—C9B—C10B	115.1 (3)
N1A—C9A—H9AA	108.5	N1B—C9B—H9BA	108.5
C10A—C9A—H9AA	108.5	C10B—C9B—H9BA	108.5
N1A—C9A—H9AB	108.5	N1B—C9B—H9BB	108.5
C10A—C9A—H9AB	108.5	C10B—C9B—H9BB	108.5
H9AA—C9A—H9AB	107.5	H9BA—C9B—H9BB	107.5
C15A—C10A—C11A	119.0 (3)	C15B—C10B—C11B	119.2 (4)
C15A—C10A—C9A	123.1 (3)	C15B—C10B—C9B	122.5 (3)
C11A—C10A—C9A	117.9 (3)	C11B—C10B—C9B	118.3 (4)
C12A—C11A—C10A	120.3 (4)	C12B—C11B—C10B	120.9 (4)
C12A—C11A—H11A	119.9	C12B—C11B—H11B	119.6
C10A—C11A—H11A	119.9	C10B—C11B—H11B	119.6
C13A—C12A—C11A	120.2 (4)	C13B—C12B—C11B	119.8 (4)
C13A—C12A—H12A	119.9	C13B—C12B—H12B	120.1
C11A—C12A—H12A	119.9	C11B—C12B—H12B	120.1
C12A—C13A—C14A	120.0 (4)	C12B—C13B—C14B	120.5 (4)
C12A—C13A—H13A	120.0	C12B—C13B—H13B	119.8
C14A—C13A—H13A	120.0	C14B—C13B—H13B	119.8
C13A—C14A—C15A	120.2 (4)	C13B—C14B—C15B	119.7 (4)
C13A—C14A—H14A	119.9	C13B—C14B—H14B	120.2
C15A—C14A—H14A	119.9	C15B—C14B—H14B	120.2
C10A—C15A—C14A	120.3 (4)	C10B—C15B—C14B	120.0 (4)
C10A—C15A—H15A	119.8	C10B—C15B—H15B	120.0
C14A—C15A—H15A	119.8	C14B—C15B—H15B	120.0
C8A—N1A—C9A	123.6 (3)	C8B—N1B—C9B	124.0 (3)
C8A—N1A—C7A	114.4 (3)	C8B—N1B—C7B	113.8 (3)
C9A—N1A—C7A	121.9 (3)	C9B—N1B—C7B	121.9 (3)
C3A—O1A—C6A	96.2 (2)	C3B—O1B—C6B	96.4 (2)
C6A—C1A—C2A—C3A	2.0 (3)	C6B—C1B—C2B—C3B	2.6 (3)
Br1A—C1A—C2A—C3A	119.8 (3)	Br1B—C1B—C2B—C3B	121.6 (3)
C6A—C1A—C2A—Br2A	126.7 (2)	C6B—C1B—C2B—Br2B	127.1 (2)
Br1A—C1A—C2A—Br2A	−115.4 (2)	Br1B—C1B—C2B—Br2B	−113.9 (2)
C1A—C2A—C3A—O1A	−37.2 (3)	C1B—C2B—C3B—O1B	−37.7 (3)
Br2A—C2A—C3A—O1A	−161.4 (2)	Br2B—C2B—C3B—O1B	−161.2 (2)
C1A—C2A—C3A—C4A	70.7 (4)	C1B—C2B—C3B—C4B	70.2 (4)
Br2A—C2A—C3A—C4A	−53.5 (4)	Br2B—C2B—C3B—C4B	−53.2 (4)
O1A—C3A—C4A—C5A	37.9 (3)	O1B—C3B—C4B—C5B	37.9 (4)
C2A—C3A—C4A—C5A	−68.4 (4)	C2B—C3B—C4B—C5B	−67.9 (4)
C3A—C4A—C5A—C8A	−114.6 (3)	C3B—C4B—C5B—C8B	−116.0 (3)
C3A—C4A—C5A—C6A	−3.4 (4)	C3B—C4B—C5B—C6B	−3.5 (4)
C2A—C1A—C6A—O1A	33.9 (3)	C2B—C1B—C6B—O1B	33.4 (3)
Br1A—C1A—C6A—O1A	−83.8 (3)	Br1B—C1B—C6B—O1B	−84.7 (3)
C2A—C1A—C6A—C7A	159.2 (3)	C2B—C1B—C6B—C7B	160.0 (3)
Br1A—C1A—C6A—C7A	41.5 (4)	Br1B—C1B—C6B—C7B	41.9 (4)
C2A—C1A—C6A—C5A	−73.4 (3)	C2B—C1B—C6B—C5B	−73.8 (3)
Br1A—C1A—C6A—C5A	168.9 (2)	Br1B—C1B—C6B—C5B	168.1 (2)
C8A—C5A—C6A—O1A	91.0 (3)	C8B—C5B—C6B—O1B	92.6 (3)
C4A—C5A—C6A—O1A	−31.6 (3)	C4B—C5B—C6B—O1B	−31.4 (3)
C8A—C5A—C6A—C7A	−24.7 (3)	C8B—C5B—C6B—C7B	−24.0 (4)
C4A—C5A—C6A—C7A	−147.3 (3)	C4B—C5B—C6B—C7B	−147.9 (3)
C8A—C5A—C6A—C1A	−161.1 (3)	C8B—C5B—C6B—C1B	−159.3 (3)
C4A—C5A—C6A—C1A	76.3 (3)	C4B—C5B—C6B—C1B	76.8 (3)
O1A—C6A—C7A—N1A	−86.1 (3)	O1B—C6B—C7B—N1B	−86.1 (3)
C1A—C6A—C7A—N1A	152.2 (3)	C1B—C6B—C7B—N1B	151.2 (3)
C5A—C6A—C7A—N1A	23.4 (3)	C5B—C6B—C7B—N1B	23.4 (4)
C4A—C5A—C8A—O2A	−52.9 (5)	C4B—C5B—C8B—O2B	−52.6 (5)
C6A—C5A—C8A—O2A	−164.9 (3)	C6B—C5B—C8B—O2B	−165.6 (4)
C4A—C5A—C8A—N1A	128.8 (3)	C4B—C5B—C8B—N1B	128.6 (4)
C6A—C5A—C8A—N1A	16.8 (4)	C6B—C5B—C8B—N1B	15.6 (4)
N1A—C9A—C10A—C15A	−12.7 (5)	N1B—C9B—C10B—C15B	−22.1 (6)
N1A—C9A—C10A—C11A	166.8 (3)	N1B—C9B—C10B—C11B	159.4 (4)
C15A—C10A—C11A—C12A	−0.5 (6)	C15B—C10B—C11B—C12B	0.1 (6)
C9A—C10A—C11A—C12A	−179.9 (4)	C9B—C10B—C11B—C12B	178.7 (4)
C10A—C11A—C12A—C13A	0.0 (6)	C10B—C11B—C12B—C13B	0.5 (7)
C11A—C12A—C13A—C14A	0.7 (6)	C11B—C12B—C13B—C14B	−1.0 (7)
C12A—C13A—C14A—C15A	−1.0 (6)	C12B—C13B—C14B—C15B	0.9 (6)
C11A—C10A—C15A—C14A	0.1 (6)	C11B—C10B—C15B—C14B	−0.2 (6)
C9A—C10A—C15A—C14A	179.6 (4)	C9B—C10B—C15B—C14B	−178.8 (4)
C13A—C14A—C15A—C10A	0.6 (6)	C13B—C14B—C15B—C10B	−0.3 (6)
O2A—C8A—N1A—C9A	−5.0 (6)	O2B—C8B—N1B—C9B	−6.4 (6)
C5A—C8A—N1A—C9A	173.3 (3)	C5B—C8B—N1B—C9B	172.4 (3)
O2A—C8A—N1A—C7A	179.3 (3)	O2B—C8B—N1B—C7B	−179.9 (4)
C5A—C8A—N1A—C7A	−2.4 (4)	C5B—C8B—N1B—C7B	−1.0 (4)
C10A—C9A—N1A—C8A	113.6 (4)	C10B—C9B—N1B—C8B	119.8 (4)
C10A—C9A—N1A—C7A	−71.0 (4)	C10B—C9B—N1B—C7B	−67.2 (5)
C6A—C7A—N1A—C8A	−13.4 (4)	C6B—C7B—N1B—C8B	−14.3 (4)
C6A—C7A—N1A—C9A	170.8 (3)	C6B—C7B—N1B—C9B	172.0 (3)
C4A—C3A—O1A—C6A	−58.3 (3)	C4B—C3B—O1B—C6B	−58.5 (3)
C2A—C3A—O1A—C6A	58.3 (3)	C2B—C3B—O1B—C6B	58.4 (3)
C7A—C6A—O1A—C3A	167.7 (3)	C7B—C6B—O1B—C3B	167.3 (3)
C1A—C6A—O1A—C3A	−58.7 (3)	C1B—C6B—O1B—C3B	−59.0 (3)
C5A—C6A—O1A—C3A	54.9 (3)	C5B—C6B—O1B—C3B	54.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1A···O2A^i	0.98	2.51	3.175 (4)	125
C4A—H4AB···Br2A	0.97	2.81	3.287 (4)	111
C5A—H5A···O2A^i	0.98	2.64	3.271 (4)	123
C7A—H7AB···O2A^i	0.97	2.53	3.186 (4)	125
C1B—H1B···O2B^ii	0.98	2.39	3.104 (4)	129
C2B—H2B···O1A	0.98	2.38	3.341 (4)	168
C4B—H4BB···Br2B	0.97	2.83	3.301 (4)	111
C5B—H5B···O2B^ii	0.98	2.57	3.247 (5)	126
C7B—H7BB···O2B^ii	0.97	2.64	3.270 (5)	123

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