Crystal structures of the two epimers from the unusual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octa­hydro-7,9a-ep­oxy­pyrrolo­[2,1-a]iso­indole-6-carb­oxy­lic acid, 5a(RS),6(SR),7(RS),9a(SR),9b(SR) and 5a(RS),6(RS),7(RS),9a(SR),9b(SR)

The two epimers from the unusual thermal C6-epimerization of 5-oxo-1,2,3,5,5a,6,7,9b-octa­hydro-7,9a-ep­oxy­pyrrolo­[2,1-a]iso­indole-6-carb­oxy­lic acid, 5a(RS),6(SR),7(RS),9a(SR),9b(SR) and 5a(RS),6(RS),7(RS),9a(SR),9b(SR) have similar geometries but differ in their hydrogen-bonded crystal-packing modes

Key indicators

Structure: Ia

• Single-crystal synchrotron study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.072
• wR factor = 0.189
• Data-to-parameter ratio = 14.7

Structure: IIa

• Single-crystal synchrotron study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.099
• wR factor = 0.240
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Datablock: Ia


Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.452 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         18 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT343_ALERT_2_G Unusual sp3      Angle Range in Main Residue for     C9A    Check
PLAT793_ALERT_4_G The Model has Chirality at C5A     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C6      (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C7      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C9A     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C9B     (Centro SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         84 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   4 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
   3 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
   6 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check




Datablock: IIa



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full value Low .      0.941 Note

Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     --  C5A     ..        6.0 s.u.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C7     --  C8      ..        6.2 s.u.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     20.628 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600        116 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density           0 Note

Alert level G
ABSMU01_ALERT_1_G  Calculation of _exptl_absorpt_correction_mu
                not performed for this radiation type.
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)       0.03 Degree
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3 Note
PLAT343_ALERT_2_G Unusual sp3      Angle Range in Main Residue for     C9A    Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  C11    ..  C11     ..       3.19 Ang.
PLAT793_ALERT_4_G The Model has Chirality at C5A     (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C6      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C7      (Centro SPGR)          S Verify
PLAT793_ALERT_4_G The Model has Chirality at C9A     (Centro SPGR)          R Verify
PLAT793_ALERT_4_G The Model has Chirality at C9B     (Centro SPGR)          R Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        144 Note

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

   2 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
   3 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

---

Computing details

For both compounds, data collection: Automar (MarXperts, 2015); cell refinement: iMOSFLM (Battye et al., 2011); data reduction: iMOSFLM (Battye et al., 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(Ia) 5a(RS),6(SR),7(RS),9a(SR),9b(SR)-5-Oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid

Crystal data

C12H13NO4	Dx = 1.415 Mg m^−3
Mr = 235.23	Melting point = 413–414 K
Monoclinic, P21/c	Synchrotron radiation, λ = 0.96990 Å
a = 11.045 (2) Å	Cell parameters from 600 reflections
b = 9.2023 (18) Å	θ = 4.5–38.0°
c = 11.062 (2) Å	µ = 0.23 mm^−1
β = 100.91 (3)°	T = 100 K
V = 1104.1 (4) Å^3	Prism, colourless
Z = 4	0.20 × 0.15 × 0.15 mm
F(000) = 496

Data collection

MAR CCD diffractometer	1864 reflections with I > 2σ(I)
φ scan	Rint = 0.085
Absorption correction: multi-scan (SCALA; Evans, 2006)	θmax = 38.5°, θmin = 4.5°
Tmin = 0.950, Tmax = 0.960	h = −13→14
12183 measured reflections	k = −11→10
2329 independent reflections	l = −13→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.072	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.189	w = 1/[σ^2(Fo^2) + (0.08P)^2 + 1.P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
2329 reflections	Δρmax = 0.43 e Å^−3
158 parameters	Δρmin = −0.43 e Å^−3
0 restraints	Extinction correction: SHELXL-2014/7 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.104 (9)

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
C1	0.8345 (2)	0.9330 (3)	0.5467 (2)	0.0330 (6)
H1A	0.8888	0.8929	0.4933	0.040*
H1B	0.8859	0.9780	0.6202	0.040*
C2	0.7415 (2)	1.0430 (3)	0.4762 (2)	0.0349 (6)
H2A	0.7799	1.1002	0.4177	0.042*
H2B	0.7123	1.1106	0.5341	0.042*
C3	0.6333 (2)	0.9507 (3)	0.4064 (2)	0.0312 (6)
H3A	0.5531	0.9989	0.4059	0.037*
H3B	0.6426	0.9320	0.3205	0.037*
N4	0.64418 (17)	0.8166 (2)	0.47832 (17)	0.0272 (5)
C5	0.60154 (19)	0.6839 (2)	0.4418 (2)	0.0253 (5)
O5	0.52224 (14)	0.65677 (18)	0.34888 (14)	0.0280 (5)
C5A	0.66529 (19)	0.5736 (2)	0.53586 (19)	0.0236 (5)
H5A	0.6166	0.5553	0.6019	0.028*
C6	0.7153 (2)	0.4306 (2)	0.4908 (2)	0.0254 (5)
H6	0.7007	0.3500	0.5470	0.030*
C7	0.8561 (2)	0.4655 (3)	0.5143 (2)	0.0296 (6)
H7	0.9050	0.4068	0.4645	0.035*
C8	0.9021 (2)	0.4591 (3)	0.6528 (2)	0.0330 (6)
H8	0.9504	0.3847	0.6980	0.040*
C9	0.8604 (2)	0.5799 (3)	0.6976 (2)	0.0302 (6)
H9	0.8737	0.6103	0.7812	0.036*
C9A	0.7874 (2)	0.6583 (2)	0.5868 (2)	0.0251 (5)
C9B	0.7500 (2)	0.8164 (3)	0.5827 (2)	0.0291 (6)
H9B	0.7224	0.8442	0.6606	0.035*
O10	0.85603 (14)	0.62038 (18)	0.49215 (14)	0.0276 (4)
C11	0.6649 (2)	0.3852 (2)	0.3585 (2)	0.0251 (5)
O11	0.71540 (16)	0.4123 (2)	0.27256 (16)	0.0374 (5)
O12	0.56401 (14)	0.30469 (18)	0.35042 (15)	0.0265 (4)
H12	0.539 (3)	0.275 (3)	0.272 (3)	0.040*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0350 (13)	0.0293 (13)	0.0289 (12)	−0.0063 (9)	−0.0086 (10)	−0.0015 (9)
C2	0.0433 (15)	0.0252 (13)	0.0318 (14)	−0.0031 (10)	−0.0039 (11)	0.0009 (9)
C3	0.0333 (13)	0.0261 (13)	0.0304 (13)	0.0025 (9)	−0.0033 (10)	0.0043 (9)
N4	0.0257 (10)	0.0236 (11)	0.0278 (10)	0.0004 (7)	−0.0064 (8)	0.0017 (7)
C5	0.0192 (10)	0.0290 (12)	0.0246 (11)	−0.0003 (8)	−0.0036 (8)	0.0016 (8)
O5	0.0233 (8)	0.0293 (9)	0.0259 (9)	−0.0010 (6)	−0.0098 (6)	0.0025 (6)
C5A	0.0190 (10)	0.0270 (12)	0.0214 (11)	−0.0001 (8)	−0.0052 (8)	0.0018 (8)
C6	0.0229 (11)	0.0254 (12)	0.0235 (11)	−0.0011 (8)	−0.0066 (8)	0.0011 (8)
C7	0.0215 (11)	0.0309 (13)	0.0314 (13)	0.0017 (9)	−0.0075 (9)	−0.0039 (9)
C8	0.0252 (11)	0.0324 (13)	0.0334 (14)	0.0030 (9)	−0.0148 (9)	0.0008 (9)
C9	0.0268 (12)	0.0341 (14)	0.0237 (12)	−0.0021 (9)	−0.0102 (9)	0.0011 (9)
C9A	0.0231 (11)	0.0260 (12)	0.0226 (11)	−0.0001 (8)	−0.0045 (8)	−0.0008 (8)
C9B	0.0269 (12)	0.0323 (14)	0.0236 (11)	0.0001 (9)	−0.0066 (9)	−0.0003 (9)
O10	0.0222 (8)	0.0303 (9)	0.0276 (9)	−0.0023 (6)	−0.0023 (6)	−0.0015 (7)
C11	0.0221 (11)	0.0246 (12)	0.0254 (12)	0.0003 (8)	−0.0036 (8)	0.0000 (8)
O11	0.0352 (10)	0.0471 (12)	0.0276 (10)	−0.0085 (8)	0.0004 (7)	−0.0016 (7)
O12	0.0205 (8)	0.0301 (9)	0.0251 (9)	−0.0027 (6)	−0.0053 (6)	−0.0030 (6)

Geometric parameters (Å, º)

C1—C9B	1.524 (4)	C6—C11	1.522 (3)
C1—C2	1.544 (3)	C6—C7	1.561 (3)
C1—H1A	0.9900	C6—H6	1.0000
C1—H1B	0.9900	C7—O10	1.446 (3)
C2—C3	1.548 (3)	C7—C8	1.522 (3)
C2—H2A	0.9900	C7—H7	1.0000
C2—H2B	0.9900	C8—C9	1.334 (4)
C3—N4	1.461 (3)	C8—H8	0.9500
C3—H3A	0.9900	C9—C9A	1.516 (3)
C3—H3B	0.9900	C9—H9	0.9500
N4—C5	1.343 (3)	C9A—O10	1.447 (3)
N4—C9B	1.480 (3)	C9A—C9B	1.511 (3)
C5—O5	1.243 (3)	C9B—H9B	1.0000
C5—C5A	1.527 (3)	C11—O11	1.216 (3)
C5A—C6	1.546 (3)	C11—O12	1.327 (3)
C5A—C9A	1.568 (3)	O12—H12	0.90 (3)
C5A—H5A	1.0000
C9B—C1—C2	102.2 (2)	C11—C6—H6	108.8
C9B—C1—H1A	111.3	C5A—C6—H6	108.8
C2—C1—H1A	111.3	C7—C6—H6	108.8
C9B—C1—H1B	111.3	O10—C7—C8	101.44 (18)
C2—C1—H1B	111.3	O10—C7—C6	101.91 (17)
H1A—C1—H1B	109.2	C8—C7—C6	107.0 (2)
C1—C2—C3	105.63 (19)	O10—C7—H7	115.0
C1—C2—H2A	110.6	C8—C7—H7	115.0
C3—C2—H2A	110.6	C6—C7—H7	115.0
C1—C2—H2B	110.6	C9—C8—C7	105.6 (2)
C3—C2—H2B	110.6	C9—C8—H8	127.2
H2A—C2—H2B	108.7	C7—C8—H8	127.2
N4—C3—C2	102.45 (18)	C8—C9—C9A	105.3 (2)
N4—C3—H3A	111.3	C8—C9—H9	127.3
C2—C3—H3A	111.3	C9A—C9—H9	127.3
N4—C3—H3B	111.3	O10—C9A—C9B	112.83 (19)
C2—C3—H3B	111.3	O10—C9A—C9	101.49 (18)
H3A—C3—H3B	109.2	C9B—C9A—C9	125.67 (19)
C5—N4—C3	128.07 (19)	O10—C9A—C5A	98.78 (16)
C5—N4—C9B	114.43 (18)	C9B—C9A—C5A	104.85 (17)
C3—N4—C9B	113.42 (18)	C9—C9A—C5A	110.12 (18)
O5—C5—N4	125.7 (2)	N4—C9B—C9A	101.29 (17)
O5—C5—C5A	126.3 (2)	N4—C9B—C1	103.16 (18)
N4—C5—C5A	108.04 (17)	C9A—C9B—C1	120.6 (2)
C5—C5A—C6	119.56 (18)	N4—C9B—H9B	110.3
C5—C5A—C9A	99.73 (17)	C9A—C9B—H9B	110.3
C6—C5A—C9A	101.74 (17)	C1—C9B—H9B	110.3
C5—C5A—H5A	111.5	C7—O10—C9A	95.65 (17)
C6—C5A—H5A	111.5	O11—C11—O12	124.4 (2)
C9A—C5A—H5A	111.5	O11—C11—C6	123.9 (2)
C11—C6—C5A	117.10 (17)	O12—C11—C6	111.56 (19)
C11—C6—C7	112.8 (2)	C11—O12—H12	109.4 (19)
C5A—C6—C7	100.16 (17)
C9B—C1—C2—C3	−35.5 (3)	C6—C5A—C9A—O10	40.32 (19)
C1—C2—C3—N4	23.1 (3)	C5—C5A—C9A—C9B	33.7 (2)
C2—C3—N4—C5	−157.3 (2)	C6—C5A—C9A—C9B	156.88 (18)
C2—C3—N4—C9B	−1.6 (3)	C5—C5A—C9A—C9	171.42 (19)
C3—N4—C5—O5	−16.7 (4)	C6—C5A—C9A—C9	−65.4 (2)
C9B—N4—C5—O5	−172.2 (2)	C5—N4—C9B—C9A	13.2 (3)
C3—N4—C5—C5A	164.6 (2)	C3—N4—C9B—C9A	−146.0 (2)
C9B—N4—C5—C5A	9.0 (3)	C5—N4—C9B—C1	138.6 (2)
O5—C5—C5A—C6	45.6 (3)	C3—N4—C9B—C1	−20.6 (3)
N4—C5—C5A—C6	−135.7 (2)	O10—C9A—C9B—N4	77.5 (2)
O5—C5—C5A—C9A	155.1 (2)	C9—C9A—C9B—N4	−157.9 (2)
N4—C5—C5A—C9A	−26.1 (2)	C5A—C9A—C9B—N4	−29.0 (2)
C5—C5A—C6—C11	−18.4 (3)	O10—C9A—C9B—C1	−35.3 (3)
C9A—C5A—C6—C11	−126.8 (2)	C9—C9A—C9B—C1	89.3 (3)
C5—C5A—C6—C7	103.9 (2)	C5A—C9A—C9B—C1	−141.8 (2)
C9A—C5A—C6—C7	−4.5 (2)	C2—C1—C9B—N4	33.3 (2)
C11—C6—C7—O10	92.5 (2)	C2—C1—C9B—C9A	145.2 (2)
C5A—C6—C7—O10	−32.8 (2)	C8—C7—O10—C9A	−50.66 (19)
C11—C6—C7—C8	−161.48 (19)	C6—C7—O10—C9A	59.66 (18)
C5A—C6—C7—C8	73.2 (2)	C9B—C9A—O10—C7	−171.63 (16)
O10—C7—C8—C9	32.0 (3)	C9—C9A—O10—C7	51.38 (18)
C6—C7—C8—C9	−74.4 (2)	C5A—C9A—O10—C7	−61.36 (16)
C7—C8—C9—C9A	0.9 (3)	C5A—C6—C11—O11	95.3 (3)
C8—C9—C9A—O10	−33.6 (2)	C7—C6—C11—O11	−20.2 (3)
C8—C9—C9A—C9B	−162.9 (2)	C5A—C6—C11—O12	−88.8 (2)
C8—C9—C9A—C5A	70.3 (3)	C7—C6—C11—O12	155.70 (19)
C5—C5A—C9A—O10	−82.84 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O5^i	0.90 (3)	1.75 (3)	2.613 (2)	157 (3)
C5A—H5A···O12^ii	1.00	2.51	3.234 (3)	129

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

(IIa) 5a(RS),6(RS),7(RS),9a(SR),9b(SR)-5-Oxo-1,2,3,5,5a,6,7,9b-octahydro-7,9a-epoxypyrrolo[2,1-a]isoindole-6-carboxylic acid

Crystal data

C12H13NO4	F(000) = 248
Mr = 235.23	Dx = 1.426 Mg m^−3
Triclinic, P1	Melting point = 414–416 K
a = 8.4700 (17) Å	Synchrotron radiation, λ = 0.96990 Å
b = 8.5100 (17) Å	Cell parameters from 500 reflections
c = 8.5900 (17) Å	θ = 3.6–36.0°
α = 94.04 (3)°	µ = 0.23 mm^−1
β = 111.12 (3)°	T = 100 K
γ = 105.17 (3)°	Prism, colourless
V = 548.0 (2) Å^3	0.15 × 0.10 × 0.10 mm
Z = 2

Data collection

MAR CCD diffractometer	1402 reflections with I > 2σ(I)
φ scan	Rint = 0.061
Absorption correction: multi-scan (SCALA; Evans, 2006)	θmax = 38.1°, θmin = 3.4°
Tmin = 0.960, Tmax = 0.969	h = −10→10
7090 measured reflections	k = −10→10
2104 independent reflections	l = −10→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.099	H-atom parameters constrained
wR(F^2) = 0.240	w = 1/[σ^2(Fo^2) + (0.06P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
2104 reflections	Δρmax = 0.45 e Å^−3
155 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL-2014/7 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: difference Fourier map	Extinction coefficient: 0.138 (11)

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
C1	0.1779 (3)	0.0068 (2)	0.2264 (2)	0.0322 (5)
H1A	0.0733	−0.0331	0.1171	0.039*
H1B	0.2531	−0.0668	0.2374	0.039*
C2	0.1215 (3)	0.0169 (2)	0.3765 (2)	0.0324 (5)
H2A	0.0900	−0.0932	0.4081	0.039*
H2B	0.0181	0.0592	0.3486	0.039*
C3	0.2874 (2)	0.1392 (2)	0.5222 (2)	0.0288 (5)
H3A	0.2529	0.2089	0.5934	0.035*
H3B	0.3628	0.0797	0.5949	0.035*
N4	0.37879 (19)	0.23864 (17)	0.42848 (16)	0.0261 (4)
C5	0.5531 (2)	0.3199 (2)	0.4832 (2)	0.0250 (4)
O5	0.65982 (17)	0.35299 (15)	0.63512 (13)	0.0299 (3)
C5A	0.5950 (2)	0.3619 (2)	0.3297 (2)	0.0233 (4)
H5A	0.5949	0.4769	0.3127	0.028*
C6	0.7574 (2)	0.32415 (19)	0.3142 (2)	0.0245 (4)
H6	0.8150	0.2754	0.4140	0.029*
C7	0.6593 (3)	0.1818 (2)	0.1503 (2)	0.0276 (5)
H7	0.7338	0.1138	0.1333	0.033*
C8	0.5722 (2)	0.2548 (2)	−0.0027 (2)	0.0264 (5)
H8	0.6108	0.2775	−0.0921	0.032*
C9	0.4292 (3)	0.2805 (2)	0.0152 (2)	0.0284 (5)
H9	0.3431	0.3223	−0.0598	0.034*
C9A	0.4358 (2)	0.2276 (2)	0.1826 (2)	0.0256 (5)
C9B	0.2840 (2)	0.1875 (2)	0.24142 (19)	0.0267 (5)
H9B	0.2022	0.2541	0.1950	0.032*
O10	0.51146 (16)	0.09341 (13)	0.18544 (14)	0.0258 (3)
C11	0.8967 (2)	0.4657 (2)	0.2990 (2)	0.0259 (5)
O11	0.88416 (17)	0.60281 (15)	0.27854 (15)	0.0338 (4)
O12	1.04071 (16)	0.42233 (14)	0.31124 (15)	0.0312 (4)
H12	1.1355	0.5093	0.3163	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0352 (10)	0.0244 (9)	0.0294 (8)	−0.0016 (8)	0.0132 (7)	−0.0032 (7)
C2	0.0364 (10)	0.0254 (9)	0.0311 (8)	−0.0003 (8)	0.0158 (7)	0.0030 (7)
C3	0.0365 (9)	0.0234 (9)	0.0290 (8)	0.0035 (8)	0.0201 (6)	0.0019 (7)
N4	0.0308 (8)	0.0214 (7)	0.0246 (6)	0.0012 (6)	0.0152 (5)	−0.0014 (5)
C5	0.0316 (9)	0.0159 (7)	0.0263 (8)	0.0045 (7)	0.0131 (6)	−0.0028 (6)
O5	0.0364 (7)	0.0281 (6)	0.0205 (5)	0.0017 (5)	0.0130 (4)	−0.0033 (5)
C5A	0.0284 (9)	0.0177 (8)	0.0227 (7)	0.0022 (7)	0.0131 (6)	−0.0005 (6)
C6	0.0355 (9)	0.0164 (8)	0.0232 (7)	0.0043 (7)	0.0165 (6)	0.0005 (6)
C7	0.0335 (9)	0.0192 (8)	0.0277 (8)	−0.0004 (7)	0.0169 (6)	−0.0048 (6)
C8	0.0373 (10)	0.0199 (8)	0.0209 (7)	0.0025 (7)	0.0158 (6)	−0.0026 (6)
C9	0.0368 (10)	0.0211 (8)	0.0229 (8)	0.0029 (8)	0.0118 (7)	−0.0001 (6)
C9A	0.0344 (9)	0.0168 (8)	0.0239 (7)	0.0043 (7)	0.0128 (6)	0.0000 (6)
C9B	0.0327 (9)	0.0214 (8)	0.0240 (8)	0.0032 (7)	0.0134 (6)	−0.0021 (6)
O10	0.0337 (6)	0.0164 (5)	0.0277 (5)	0.0033 (5)	0.0165 (4)	−0.0009 (4)
C11	0.0316 (9)	0.0227 (9)	0.0204 (7)	0.0024 (7)	0.0126 (6)	−0.0045 (6)
O11	0.0375 (7)	0.0228 (6)	0.0390 (6)	0.0042 (6)	0.0170 (5)	0.0031 (5)
O12	0.0309 (7)	0.0232 (6)	0.0403 (6)	0.0040 (5)	0.0189 (5)	0.0015 (5)

Geometric parameters (Å, º)

C1—C2	1.532 (3)	C6—C11	1.500 (3)
C1—C9B	1.534 (3)	C6—C7	1.590 (2)
C1—H1A	0.9900	C6—H6	1.0000
C1—H1B	0.9900	C7—O10	1.427 (2)
C2—C3	1.552 (2)	C7—C8	1.521 (3)
C2—H2A	0.9900	C7—H7	1.0000
C2—H2B	0.9900	C8—C9	1.344 (3)
C3—N4	1.472 (2)	C8—H8	0.9500
C3—H3A	0.9900	C9—C9A	1.522 (2)
C3—H3B	0.9900	C9—H9	0.9500
N4—C5	1.341 (2)	C9A—O10	1.446 (2)
N4—C9B	1.485 (2)	C9A—C9B	1.513 (3)
C5—O5	1.250 (2)	C9B—H9B	1.0000
C5—C5A	1.526 (3)	C11—O11	1.218 (2)
C5A—C6	1.540 (3)	C11—O12	1.336 (2)
C5A—C9A	1.576 (2)	O12—H12	0.9239
C5A—H5A	1.0000
C2—C1—C9B	102.15 (14)	C11—C6—H6	108.7
C2—C1—H1A	111.3	C5A—C6—H6	108.7
C9B—C1—H1A	111.3	C7—C6—H6	108.7
C2—C1—H1B	111.3	O10—C7—C8	102.71 (15)
C9B—C1—H1B	111.3	O10—C7—C6	99.48 (13)
H1A—C1—H1B	109.2	C8—C7—C6	109.15 (14)
C1—C2—C3	104.39 (16)	O10—C7—H7	114.6
C1—C2—H2A	110.9	C8—C7—H7	114.6
C3—C2—H2A	110.9	C6—C7—H7	114.6
C1—C2—H2B	110.9	C9—C8—C7	105.52 (17)
C3—C2—H2B	110.9	C9—C8—H8	127.2
H2A—C2—H2B	108.9	C7—C8—H8	127.2
N4—C3—C2	102.16 (13)	C8—C9—C9A	104.59 (17)
N4—C3—H3A	111.3	C8—C9—H9	127.7
C2—C3—H3A	111.3	C9A—C9—H9	127.7
N4—C3—H3B	111.3	O10—C9A—C9B	111.77 (14)
C2—C3—H3B	111.3	O10—C9A—C9	102.12 (14)
H3A—C3—H3B	109.2	C9B—C9A—C9	126.44 (16)
C5—N4—C3	127.10 (15)	O10—C9A—C5A	100.18 (14)
C5—N4—C9B	115.10 (15)	C9B—C9A—C5A	105.83 (13)
C3—N4—C9B	113.07 (13)	C9—C9A—C5A	107.50 (14)
O5—C5—N4	124.50 (18)	N4—C9B—C9A	102.11 (13)
O5—C5—C5A	127.21 (17)	N4—C9B—C1	101.06 (14)
N4—C5—C5A	108.28 (14)	C9A—C9B—C1	120.38 (16)
C5—C5A—C6	117.75 (15)	N4—C9B—H9B	110.7
C5—C5A—C9A	101.00 (14)	C9A—C9B—H9B	110.7
C6—C5A—C9A	101.86 (13)	C1—C9B—H9B	110.7
C5—C5A—H5A	111.7	C7—O10—C9A	96.02 (13)
C6—C5A—H5A	111.7	O11—C11—O12	123.30 (17)
C9A—C5A—H5A	111.7	O11—C11—C6	125.93 (18)
C11—C6—C5A	117.00 (15)	O12—C11—C6	110.77 (15)
C11—C6—C7	113.55 (15)	C11—O12—H12	113.8
C5A—C6—C7	99.72 (13)
C9B—C1—C2—C3	−40.2 (2)	C6—C5A—C9A—O10	32.99 (16)
C1—C2—C3—N4	24.99 (19)	C5—C5A—C9A—C9B	27.56 (18)
C2—C3—N4—C5	−154.32 (18)	C6—C5A—C9A—C9B	149.26 (14)
C2—C3—N4—C9B	−0.1 (2)	C5—C5A—C9A—C9	165.01 (15)
C3—N4—C5—O5	−16.0 (3)	C6—C5A—C9A—C9	−73.29 (18)
C9B—N4—C5—O5	−169.80 (16)	C5—N4—C9B—C9A	8.4 (2)
C3—N4—C5—C5A	163.66 (15)	C3—N4—C9B—C9A	−149.09 (15)
C9B—N4—C5—C5A	9.9 (2)	C5—N4—C9B—C1	133.04 (17)
O5—C5—C5A—C6	47.1 (2)	C3—N4—C9B—C1	−24.4 (2)
N4—C5—C5A—C6	−132.62 (15)	O10—C9A—C9B—N4	85.85 (15)
O5—C5—C5A—C9A	156.89 (18)	C9—C9A—C9B—N4	−148.99 (15)
N4—C5—C5A—C9A	−22.81 (19)	C5A—C9A—C9B—N4	−22.27 (18)
C5—C5A—C6—C11	−123.93 (16)	O10—C9A—C9B—C1	−24.8 (2)
C9A—C5A—C6—C11	126.75 (15)	C9—C9A—C9B—C1	100.3 (2)
C5—C5A—C6—C7	113.23 (14)	C5A—C9A—C9B—C1	−132.96 (15)
C9A—C5A—C6—C7	3.91 (16)	C2—C1—C9B—N4	38.51 (18)
C11—C6—C7—O10	−165.65 (15)	C2—C1—C9B—C9A	149.76 (16)
C5A—C6—C7—O10	−40.40 (16)	C8—C7—O10—C9A	−49.46 (13)
C11—C6—C7—C8	−58.5 (2)	C6—C7—O10—C9A	62.79 (14)
C5A—C6—C7—C8	66.71 (18)	C9B—C9A—O10—C7	−171.68 (12)
O10—C7—C8—C9	30.75 (16)	C9—C9A—O10—C7	50.59 (14)
C6—C7—C8—C9	−74.15 (18)	C5A—C9A—O10—C7	−59.96 (14)
C7—C8—C9—C9A	1.83 (16)	C5A—C6—C11—O11	−8.9 (2)
C8—C9—C9A—O10	−33.38 (16)	C7—C6—C11—O11	106.5 (2)
C8—C9—C9A—C9B	−162.43 (15)	C5A—C6—C11—O12	171.02 (12)
C8—C9—C9A—C5A	71.53 (17)	C7—C6—C11—O12	−73.58 (19)
C5—C5A—C9A—O10	−88.71 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O5^i	0.92	1.70	2.607 (2)	165
C9—H9···O11^ii	0.95	2.42	3.362 (3)	172

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