5-Hydr­oxy-4-methyl-4-aza­tricyclo[5.2.2.0^2,6]undec-8-en-3-one

Two independent mol­ecules (A and B) comprise the asymmetric unit in the crystal structure of the title compound, C₁₁H₁₅NO₂. The cyclo­hexane ring adopts a boat configuration, as does the fused cyclohexene ring that bridges the cyclohexane ring. The crystal packing is stabilized by inter­molecular O—H...O hydrogen bonding between the hydroxyl H atom of mol­ecule A and the ketone O atom of mol­ecule B and vice versa. These link the mol­ecules into chains running diagonally along the bc face of the unit cell.

Key indicators

• Single-crystal X-ray study
• T = 203 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.084
• Data-to-parameter ratio = 24.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         36 Perc.

Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.730
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         26
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C11 H15 N O2

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2A    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C2B    = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C3A    = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C3B    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C6A    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C6B    = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C7A    = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C7B    = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of C8A    = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C8B    = ...          S

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
  10 ALERT level G = General alerts; check

  10 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
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

5-Hydroxy-4-methyl-4-aza-tricyclo[5.2.2.0,2,6]undecan-3-one was synthesized to determine whether the cyclic imide functionality can be reduced from 4-methyl-4-aza-tricyclo[5.2.2.0,2,6]undec-8-ene-3,5-dione (Birney et al., 2002) to a functionalized pyrrole using diisobutylaluminium hydride (DIBAL-H). This reaction was carried out to determine if a stepwise reduction of a cyclic imide into a pyrrole could use DIBAL-H instead of a more complex synthetic process (Stephan et al., 1988). These pyrrole derivatives are used in a number of materials, especially intramolecularly hydrogen-bonded conjugated polymers (Pollack et al., 1997). They are also used in the protonation and subsequent intramolecular hydrogen bonding as a method to control chain structure and to tune luminescence in heteroatomic conjugated polymers (Monkman et al., 2002). A new pyrrole derivative (I), C₁₁H₁₅NO₂, was prepared and its crystal structure is reported herein.

Compound (I) crystallizes with two independent molecules (A & B) in the asymmetric unit (Fig. 1). The angle between the mean planes of cyclohexane and fused 4-methyl-4-aza-tricyclo-3-one group is 23.5 (4) ° [A] and 25.1 (2)° [B]. The cyclohexane ring is in a boat configuration with puckering parameters Q, θ and ϕ of 0.8771 (15) Å, 91.61 (10)° and 63.05 (10)°, respectively for C2A—C7A in A, and 0.8784 (16) Å, 90.79 (10)° and 61.45 (10)°, respectively for C2B—C7B in B (Cremer & Pople, 1975). The bridged, 6-membered [5.2.2.0,2,6] group is also in a boat configuration with puckering parameters Q, θ and ϕ of 0.7885 (16) Å, 90.14 (12)° and 358.87 (12)° for C3A–C6A,C10A,C11A in A; 0.7959 (16) Å, 90.24 (12)° and 359.24 (12)° for C3B—C6B,C10B,C11B in B. The crystal packing is stabilized by intermolecular O—H···O hydrogen bonding (Table 1) between the hydroxyl hydrogen atom of molecule A [O2A–H2AA] to the ketone oxygen atom of molecule B [O1B] and vice versa, which link the molecules into chains diagonal along the bc face of the unit cell (Fig. 2).

Related literature

For related structures, see: Pollack et al. (1997); Monkman et al. (2002). For related literature, see: Birney et al. (2002); Stephan et al. (1988); Cremer & Pople (1975).

S2. Experimental

4-Methyl-4-aza-tricyclo[5.2.2.0,2,6]undec-8-ene-3,5-dione (0.50 g), produced from the Diels–Alder synthesis of N-methyl maleimide and 1,3 cyclohexadiene, was dissolved in THF (30 ml) under nitrogen in an ice bath. DIBAL-H, (5.2 ml) was added dropwise for 5 min and allowed to stir for 3 h. The reaction was then stopped. The product was extracted using ethyl acetate and washed 3x with sat. NaHCO₃. This was dried over MgSO₄ to yield 0.29 g of product. Crystals were obtained from the slow evaporation of methanol solution of (I).

S3. Refinement

The hydroxyl hydrogen atoms (H2AA & H2BA) were located in a difference Fourier map and along with all other H atoms were placed in their calculated positions and were then refined using the riding model approximation with O—H = 0.83 Å and C—H = 0.94 - 0.99 Å, and with U_iso(H) = 1.2–1.5U_eq(C, O).

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: WinGX (Farrugia, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

	Fig. 1. Molecular structure of (I), showing atom labeling for the two independent molecules (A & B) and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of C11H15NO2 viewed down the a axis. Dashed lines indicate O2A–H2AA···O1B and O2B–H2BA···O1A hydrogen bonds.

5-Hydroxy-4-methyl-4-azatricyclo[5.2.2.0^2,6]undec-8-en-3-one

Crystal data

C11H15NO2	Z = 4
Mr = 193.24	F(000) = 416
Triclinic, P1	Dx = 1.302 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0426 (10) Å	Cell parameters from 2564 reflections
b = 9.409 (3) Å	θ = 4.8–32.4°
c = 12.260 (3) Å	µ = 0.09 mm^−1
α = 108.89 (2)°	T = 203 K
β = 91.454 (13)°	Chunk, colourless
γ = 91.817 (16)°	0.55 × 0.46 × 0.36 mm
V = 985.8 (4) Å^3

Data collection

Oxford Diffraction Gemini R CCD diffractometer	2308 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 32.5°, θmin = 4.8°
Detector resolution: 10.5081 pixels mm^-1	h = −13→12
ϕ and ω scans	k = −13→13
12514 measured reflections	l = −18→18
6368 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H-atom parameters constrained
S = 0.73	w = 1/[σ^2(Fo^2) + (0.0322P)^2] where P = (Fo^2 + 2Fc^2)/3
6368 reflections	(Δ/σ)max = 0.007
257 parameters	Δρmax = 0.22 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1A	0.16069 (9)	0.52439 (10)	0.07775 (8)	0.0314 (2)
O2A	0.36646 (9)	0.25659 (10)	−0.24154 (8)	0.0366 (3)
H2AA	0.3548	0.1782	−0.2974	0.055*
O1B	0.33481 (10)	1.00085 (10)	0.57185 (8)	0.0333 (2)
O2B	0.12572 (10)	0.80442 (10)	0.22133 (9)	0.0387 (3)
H2BA	0.1357	0.7174	0.1777	0.058*
N1A	0.20075 (11)	0.34330 (12)	−0.09313 (9)	0.0276 (3)
N1B	0.28780 (11)	0.85683 (12)	0.38432 (10)	0.0284 (3)
C1A	0.18021 (13)	0.48518 (14)	−0.02746 (12)	0.0247 (3)
C2A	0.18082 (14)	0.58569 (14)	−0.10129 (11)	0.0267 (3)
H2AB	0.0796	0.6204	−0.1068	0.032*
C3A	0.28881 (15)	0.72297 (14)	−0.05591 (12)	0.0308 (3)
H3AA	0.2615	0.7893	0.0210	0.037*
C4A	0.28725 (17)	0.80663 (16)	−0.14502 (13)	0.0406 (4)
H4AA	0.1869	0.8383	−0.1546	0.049*
H4AB	0.3532	0.8967	−0.1177	0.049*
C5A	0.33856 (17)	0.70269 (16)	−0.26115 (13)	0.0411 (4)
H5AA	0.4280	0.7467	−0.2831	0.049*
H5AB	0.2612	0.6912	−0.3212	0.049*
C6A	0.37122 (15)	0.54791 (15)	−0.25038 (12)	0.0333 (4)
H6AA	0.4094	0.4802	−0.3230	0.040*
C7A	0.22374 (14)	0.48369 (14)	−0.22132 (11)	0.0268 (3)
H7AA	0.1461	0.4857	−0.2792	0.032*
C8A	0.22836 (14)	0.32299 (14)	−0.21366 (12)	0.0282 (3)
H8AA	0.1485	0.2580	−0.2639	0.034*
C9A	0.18835 (15)	0.21534 (15)	−0.05272 (13)	0.0356 (4)
H9AA	0.1873	0.2500	0.0309	0.053*
H9AB	0.2721	0.1525	−0.0777	0.053*
H9AC	0.0973	0.1577	−0.0842	0.053*
C10A	0.48098 (15)	0.57138 (15)	−0.15213 (14)	0.0351 (4)
H10A	0.5724	0.5249	−0.1612	0.042*
C11A	0.43988 (15)	0.66246 (15)	−0.05131 (13)	0.0343 (4)
H11A	0.4996	0.6869	0.0166	0.041*
C1B	0.31536 (14)	0.98754 (14)	0.46820 (12)	0.0257 (3)
C2B	0.32041 (15)	1.11280 (14)	0.41787 (11)	0.0282 (3)
H2BB	0.4225	1.1572	0.4259	0.034*
C3B	0.21215 (15)	1.23657 (14)	0.47498 (12)	0.0319 (4)
H3BA	0.2370	1.2838	0.5583	0.038*
C4B	0.22084 (17)	1.35259 (16)	0.41135 (13)	0.0416 (4)
H4BA	0.3224	1.3945	0.4170	0.050*
H4BB	0.1559	1.4351	0.4469	0.050*
C5B	0.17286 (18)	1.27657 (16)	0.28377 (13)	0.0438 (4)
H5BA	0.2532	1.2868	0.2343	0.053*
H5BB	0.0863	1.3252	0.2646	0.053*
C6B	0.13431 (15)	1.10831 (15)	0.26263 (13)	0.0362 (4)
H6BA	0.0980	1.0575	0.1821	0.043*
C7B	0.27679 (14)	1.03841 (15)	0.28943 (12)	0.0299 (3)
H7BA	0.3570	1.0593	0.2426	0.036*
C8B	0.26488 (15)	0.86870 (15)	0.26949 (12)	0.0297 (3)
H8BA	0.3442	0.8178	0.2189	0.036*
C9B	0.28810 (16)	0.71219 (15)	0.40165 (14)	0.0382 (4)
H9BA	0.2857	0.7261	0.4835	0.057*
H9BB	0.3771	0.6615	0.3707	0.057*
H9BC	0.2017	0.6518	0.3624	0.057*
C10B	0.01956 (16)	1.09860 (15)	0.34593 (15)	0.0379 (4)
H10B	−0.0733	1.0489	0.3223	0.045*
C11B	0.05950 (16)	1.16562 (15)	0.45542 (14)	0.0368 (4)
H11B	−0.0030	1.1684	0.5161	0.044*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0365 (6)	0.0309 (5)	0.0230 (6)	−0.0003 (4)	0.0021 (5)	0.0035 (4)
O2A	0.0326 (6)	0.0336 (6)	0.0340 (7)	0.0079 (4)	0.0020 (5)	−0.0032 (5)
O1B	0.0431 (6)	0.0312 (6)	0.0239 (6)	0.0069 (4)	−0.0006 (5)	0.0063 (4)
O2B	0.0352 (6)	0.0305 (6)	0.0381 (7)	0.0002 (4)	−0.0047 (5)	−0.0053 (5)
N1A	0.0320 (7)	0.0217 (6)	0.0265 (7)	0.0021 (5)	0.0005 (5)	0.0043 (5)
N1B	0.0332 (7)	0.0240 (6)	0.0250 (7)	0.0014 (5)	0.0023 (6)	0.0037 (6)
C1A	0.0184 (7)	0.0268 (8)	0.0262 (8)	−0.0002 (6)	−0.0007 (6)	0.0050 (7)
C2A	0.0236 (7)	0.0258 (7)	0.0292 (9)	0.0055 (6)	0.0002 (6)	0.0068 (7)
C3A	0.0400 (9)	0.0239 (8)	0.0261 (8)	−0.0020 (7)	0.0042 (7)	0.0047 (6)
C4A	0.0484 (10)	0.0314 (8)	0.0471 (11)	0.0024 (7)	0.0038 (8)	0.0194 (8)
C5A	0.0447 (9)	0.0449 (10)	0.0402 (10)	−0.0012 (8)	0.0016 (8)	0.0233 (8)
C6A	0.0316 (8)	0.0345 (8)	0.0304 (9)	0.0042 (7)	0.0042 (7)	0.0052 (7)
C7A	0.0241 (7)	0.0294 (8)	0.0234 (8)	0.0021 (6)	−0.0033 (6)	0.0038 (6)
C8A	0.0267 (8)	0.0286 (8)	0.0245 (8)	0.0006 (6)	0.0003 (6)	0.0019 (6)
C9A	0.0397 (9)	0.0277 (8)	0.0384 (9)	−0.0026 (6)	−0.0002 (7)	0.0101 (7)
C10A	0.0266 (8)	0.0352 (8)	0.0457 (10)	−0.0025 (7)	0.0038 (7)	0.0164 (8)
C11A	0.0304 (8)	0.0329 (8)	0.0387 (10)	−0.0094 (7)	−0.0071 (7)	0.0123 (8)
C1B	0.0232 (8)	0.0266 (8)	0.0260 (9)	0.0042 (6)	0.0025 (6)	0.0066 (7)
C2B	0.0274 (8)	0.0261 (8)	0.0284 (9)	−0.0022 (6)	−0.0022 (6)	0.0057 (6)
C3B	0.0487 (9)	0.0241 (8)	0.0227 (8)	0.0040 (7)	−0.0008 (7)	0.0074 (6)
C4B	0.0537 (10)	0.0295 (8)	0.0440 (10)	−0.0007 (7)	−0.0017 (8)	0.0158 (8)
C5B	0.0539 (10)	0.0421 (10)	0.0425 (11)	−0.0025 (8)	−0.0015 (8)	0.0244 (8)
C6B	0.0401 (9)	0.0369 (9)	0.0304 (9)	−0.0030 (7)	−0.0084 (7)	0.0103 (7)
C7B	0.0268 (8)	0.0374 (8)	0.0253 (8)	−0.0019 (6)	0.0035 (6)	0.0102 (7)
C8B	0.0250 (8)	0.0346 (8)	0.0249 (9)	0.0008 (6)	0.0014 (7)	0.0031 (7)
C9B	0.0466 (9)	0.0234 (8)	0.0445 (10)	0.0050 (7)	0.0067 (8)	0.0104 (7)
C10B	0.0294 (8)	0.0297 (8)	0.0555 (12)	0.0025 (7)	−0.0028 (8)	0.0154 (8)
C11B	0.0376 (9)	0.0323 (8)	0.0482 (11)	0.0119 (7)	0.0179 (8)	0.0216 (8)

Geometric parameters (Å, º)

O1A—C1A	1.2404 (15)	C9A—H9AA	0.9700
O2A—C8A	1.4140 (14)	C9A—H9AB	0.9700
O2A—H2AA	0.8300	C9A—H9AC	0.9700
O1B—C1B	1.2432 (15)	C10A—C11A	1.3259 (19)
O2B—C8B	1.4073 (16)	C10A—H10A	0.9400
O2B—H2BA	0.8300	C11A—H11A	0.9400
N1A—C1A	1.3387 (16)	C1B—C2B	1.4970 (19)
N1A—C9A	1.4451 (17)	C2B—C7B	1.5370 (19)
N1A—C8A	1.4565 (16)	C2B—C3B	1.5440 (17)
N1B—C1B	1.3345 (17)	C2B—H2BB	0.9900
N1B—C9B	1.4438 (17)	C3B—C11B	1.493 (2)
N1B—C8B	1.4581 (17)	C3B—C4B	1.5347 (19)
C1A—C2A	1.5060 (19)	C3B—H3BA	0.9900
C2A—C3A	1.5358 (19)	C4B—C5B	1.539 (2)
C2A—C7A	1.5412 (17)	C4B—H4BA	0.9800
C2A—H2AB	0.9900	C4B—H4BB	0.9800
C3A—C11A	1.5031 (18)	C5B—C6B	1.546 (2)
C3A—C4A	1.5396 (19)	C5B—H5BA	0.9800
C3A—H3AA	0.9900	C5B—H5BB	0.9800
C4A—C5A	1.5361 (19)	C6B—C10B	1.4954 (19)
C4A—H4AA	0.9800	C6B—C7B	1.5404 (19)
C4A—H4AB	0.9800	C6B—H6BA	0.9900
C5A—C6A	1.5413 (19)	C7B—C8B	1.5350 (19)
C5A—H5AA	0.9800	C7B—H7BA	0.9900
C5A—H5AB	0.9800	C8B—H8BA	0.9900
C6A—C10A	1.496 (2)	C9B—H9BA	0.9700
C6A—C7A	1.5436 (18)	C9B—H9BB	0.9700
C6A—H6AA	0.9900	C9B—H9BC	0.9700
C7A—C8A	1.5468 (18)	C10B—C11B	1.320 (2)
C7A—H7AA	0.9900	C10B—H10B	0.9400
C8A—H8AA	0.9900	C11B—H11B	0.9400
C8A—O2A—H2AA	109.5	C6A—C10A—H10A	122.4
C8B—O2B—H2BA	109.5	C10A—C11A—C3A	113.66 (14)
C1A—N1A—C9A	124.14 (11)	C10A—C11A—H11A	123.2
C1A—N1A—C8A	115.08 (11)	C3A—C11A—H11A	123.2
C9A—N1A—C8A	120.68 (11)	O1B—C1B—N1B	124.37 (13)
C1B—N1B—C9B	123.98 (12)	O1B—C1B—C2B	126.00 (13)
C1B—N1B—C8B	114.83 (12)	N1B—C1B—C2B	109.63 (12)
C9B—N1B—C8B	121.10 (11)	C1B—C2B—C7B	105.14 (11)
O1A—C1A—N1A	124.04 (13)	C1B—C2B—C3B	112.38 (10)
O1A—C1A—C2A	126.28 (12)	C7B—C2B—C3B	110.17 (11)
N1A—C1A—C2A	109.67 (12)	C1B—C2B—H2BB	109.7
C1A—C2A—C3A	113.55 (12)	C7B—C2B—H2BB	109.7
C1A—C2A—C7A	104.81 (10)	C3B—C2B—H2BB	109.7
C3A—C2A—C7A	110.95 (10)	C11B—C3B—C4B	108.09 (12)
C1A—C2A—H2AB	109.1	C11B—C3B—C2B	107.59 (11)
C3A—C2A—H2AB	109.1	C4B—C3B—C2B	107.31 (11)
C7A—C2A—H2AB	109.1	C11B—C3B—H3BA	111.2
C11A—C3A—C2A	106.35 (10)	C4B—C3B—H3BA	111.2
C11A—C3A—C4A	108.68 (11)	C2B—C3B—H3BA	111.2
C2A—C3A—C4A	107.56 (12)	C3B—C4B—C5B	109.51 (12)
C11A—C3A—H3AA	111.3	C3B—C4B—H4BA	109.8
C2A—C3A—H3AA	111.3	C5B—C4B—H4BA	109.8
C4A—C3A—H3AA	111.3	C3B—C4B—H4BB	109.8
C5A—C4A—C3A	109.68 (11)	C5B—C4B—H4BB	109.8
C5A—C4A—H4AA	109.7	H4BA—C4B—H4BB	108.2
C3A—C4A—H4AA	109.7	C4B—C5B—C6B	109.16 (12)
C5A—C4A—H4AB	109.7	C4B—C5B—H5BA	109.8
C3A—C4A—H4AB	109.7	C6B—C5B—H5BA	109.8
H4AA—C4A—H4AB	108.2	C4B—C5B—H5BB	109.8
C4A—C5A—C6A	109.33 (11)	C6B—C5B—H5BB	109.8
C4A—C5A—H5AA	109.8	H5BA—C5B—H5BB	108.3
C6A—C5A—H5AA	109.8	C10B—C6B—C7B	109.17 (12)
C4A—C5A—H5AB	109.8	C10B—C6B—C5B	107.80 (11)
C6A—C5A—H5AB	109.8	C7B—C6B—C5B	106.82 (12)
H5AA—C5A—H5AB	108.3	C10B—C6B—H6BA	111.0
C10A—C6A—C5A	108.20 (12)	C7B—C6B—H6BA	111.0
C10A—C6A—C7A	109.15 (12)	C5B—C6B—H6BA	111.0
C5A—C6A—C7A	106.43 (10)	C8B—C7B—C2B	105.91 (11)
C10A—C6A—H6AA	111.0	C8B—C7B—C6B	115.58 (11)
C5A—C6A—H6AA	111.0	C2B—C7B—C6B	108.49 (10)
C7A—C6A—H6AA	111.0	C8B—C7B—H7BA	108.9
C2A—C7A—C6A	107.76 (11)	C2B—C7B—H7BA	108.9
C2A—C7A—C8A	106.03 (10)	C6B—C7B—H7BA	108.9
C6A—C7A—C8A	115.39 (10)	O2B—C8B—N1B	110.62 (11)
C2A—C7A—H7AA	109.2	O2B—C8B—C7B	112.23 (11)
C6A—C7A—H7AA	109.2	N1B—C8B—C7B	104.12 (11)
C8A—C7A—H7AA	109.2	O2B—C8B—H8BA	109.9
O2A—C8A—N1A	109.21 (11)	N1B—C8B—H8BA	109.9
O2A—C8A—C7A	113.56 (10)	C7B—C8B—H8BA	109.9
N1A—C8A—C7A	103.97 (10)	N1B—C9B—H9BA	109.5
O2A—C8A—H8AA	110.0	N1B—C9B—H9BB	109.5
N1A—C8A—H8AA	110.0	H9BA—C9B—H9BB	109.5
C7A—C8A—H8AA	110.0	N1B—C9B—H9BC	109.5
N1A—C9A—H9AA	109.5	H9BA—C9B—H9BC	109.5
N1A—C9A—H9AB	109.5	H9BB—C9B—H9BC	109.5
H9AA—C9A—H9AB	109.5	C11B—C10B—C6B	114.46 (14)
N1A—C9A—H9AC	109.5	C11B—C10B—H10B	122.8
H9AA—C9A—H9AC	109.5	C6B—C10B—H10B	122.8
H9AB—C9A—H9AC	109.5	C10B—C11B—C3B	114.51 (13)
C11A—C10A—C6A	115.14 (12)	C10B—C11B—H11B	122.7
C11A—C10A—H10A	122.4	C3B—C11B—H11B	122.7
C9A—N1A—C1A—O1A	6.4 (2)	C9B—N1B—C1B—O1B	−4.9 (2)
C8A—N1A—C1A—O1A	−177.31 (11)	C8B—N1B—C1B—O1B	178.45 (11)
C9A—N1A—C1A—C2A	−172.17 (11)	C9B—N1B—C1B—C2B	174.51 (11)
C8A—N1A—C1A—C2A	4.11 (15)	C8B—N1B—C1B—C2B	−2.10 (14)
O1A—C1A—C2A—C3A	53.72 (16)	O1B—C1B—C2B—C7B	−175.46 (12)
N1A—C1A—C2A—C3A	−127.73 (11)	N1B—C1B—C2B—C7B	5.11 (13)
O1A—C1A—C2A—C7A	174.97 (12)	O1B—C1B—C2B—C3B	−55.60 (17)
N1A—C1A—C2A—C7A	−6.48 (14)	N1B—C1B—C2B—C3B	124.96 (12)
C1A—C2A—C3A—C11A	58.84 (13)	C1B—C2B—C3B—C11B	−60.52 (15)
C7A—C2A—C3A—C11A	−58.90 (14)	C7B—C2B—C3B—C11B	56.37 (14)
C1A—C2A—C3A—C4A	175.14 (10)	C1B—C2B—C3B—C4B	−176.62 (12)
C7A—C2A—C3A—C4A	57.39 (13)	C7B—C2B—C3B—C4B	−59.73 (14)
C11A—C3A—C4A—C5A	53.87 (15)	C11B—C3B—C4B—C5B	−54.41 (15)
C2A—C3A—C4A—C5A	−60.89 (14)	C2B—C3B—C4B—C5B	61.36 (15)
C3A—C4A—C5A—C6A	1.25 (16)	C3B—C4B—C5B—C6B	−0.81 (16)
C4A—C5A—C6A—C10A	−55.20 (14)	C4B—C5B—C6B—C10B	55.33 (15)
C4A—C5A—C6A—C7A	62.00 (15)	C4B—C5B—C6B—C7B	−61.89 (14)
C1A—C2A—C7A—C6A	−117.75 (12)	C1B—C2B—C7B—C8B	−6.01 (13)
C3A—C2A—C7A—C6A	5.20 (14)	C3B—C2B—C7B—C8B	−127.31 (11)
C1A—C2A—C7A—C8A	6.34 (13)	C1B—C2B—C7B—C6B	118.66 (11)
C3A—C2A—C7A—C8A	129.29 (11)	C3B—C2B—C7B—C6B	−2.65 (15)
C10A—C6A—C7A—C2A	51.26 (14)	C10B—C6B—C7B—C8B	65.93 (15)
C5A—C6A—C7A—C2A	−65.30 (14)	C5B—C6B—C7B—C8B	−177.76 (11)
C10A—C6A—C7A—C8A	−66.97 (14)	C10B—C6B—C7B—C2B	−52.80 (15)
C5A—C6A—C7A—C8A	176.47 (12)	C5B—C6B—C7B—C2B	63.52 (14)
C1A—N1A—C8A—O2A	121.68 (11)	C1B—N1B—C8B—O2B	−122.62 (12)
C9A—N1A—C8A—O2A	−61.90 (15)	C9B—N1B—C8B—O2B	60.66 (14)
C1A—N1A—C8A—C7A	0.15 (14)	C1B—N1B—C8B—C7B	−1.86 (14)
C9A—N1A—C8A—C7A	176.57 (11)	C9B—N1B—C8B—C7B	−178.57 (10)
C2A—C7A—C8A—O2A	−122.74 (11)	C2B—C7B—C8B—O2B	124.52 (11)
C6A—C7A—C8A—O2A	−3.56 (16)	C6B—C7B—C8B—O2B	4.39 (16)
C2A—C7A—C8A—N1A	−4.16 (13)	C2B—C7B—C8B—N1B	4.85 (13)
C6A—C7A—C8A—N1A	115.02 (12)	C6B—C7B—C8B—N1B	−115.29 (12)
C5A—C6A—C10A—C11A	57.17 (15)	C7B—C6B—C10B—C11B	58.18 (15)
C7A—C6A—C10A—C11A	−58.26 (15)	C5B—C6B—C10B—C11B	−57.51 (16)
C6A—C10A—C11A—C3A	0.68 (17)	C6B—C10B—C11B—C3B	−0.69 (17)
C2A—C3A—C11A—C10A	57.79 (15)	C4B—C3B—C11B—C10B	58.48 (15)
C4A—C3A—C11A—C10A	−57.75 (15)	C2B—C3B—C11B—C10B	−57.10 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2AA···O1B^i	0.83	1.90	2.7322 (16)	178
O2B—H2BA···O1A	0.83	1.86	2.6868 (16)	179

Symmetry code: (i) x, y−1, z−1.