Structural and theoretical study of four novel norcantharidine derivatives: two new cases of conditional isomorphism

Structural and theoretical studies of four novel 5,6-de­hydro­norcantharidine (DNCA)/norcantharidine (NCA) derivatives, namely (3aR,4S,7R,7aS)-2-phenyl-3a,4,7,7a-tetra­hydro-4,7-ep­oxy-1H-iso­indole-1,3(2H)-dione, C₁₄H₁₁NO₃ (DNCA-A), (3aR,4S,7R,7aS)-2-(4-nitro­phen­yl)-3a,4,7,7a-tetra­hydro-4,7-ep­oxy-1H-iso­indole-1,3(2H)-dione, C₁₄H₁₀N₂O₅ (DNCA-NA), (3aR,4S,7R,7aS)-2-(4-nitro­phen­yl)-3a,4,5,6,7,7a-hexa­hydro-1H-4,7-ep­oxy­iso­indole-1,3(2H)-dione, C₁₄H₁₂N₂O₅ (NCA-NA), and (3aR,4S,7R,7aS)-2-(2-hy­droxy­eth­yl)-3a,4,5,6,7,7a-hexa­hydro-1H-4,7-ep­oxy­iso­indole-1,3(2H)-dione, C₁₀H₁₃NO₄ (NCA-AE), are reported. The supra­molecular inter­actions and single-crystal structural characteristics of these mol­ecules, together with the crystal structures of four other similar mol­ecules, i.e. NCA-A (the 4-phenyl derivative of NCA-NA), DNCA-AE (the 5,6-unsaturated derivative of NCA-AE), DNCA and NCA, were analysed. Surprisingly, DNCA-A and NCA-A, as well as DNCA–NA and NCA-NA, proved to be isomorphic, while DNCA-AE and NCA-AE, as well as DNCA and NCA, have very different crystal structures. These are very rare iso­structural examples between unsaturated and saturated oxanorbornene/oxanorbornane derivatives. To further explore how noncovalent inter­actions (NCIs) affect the degree of isomorphism in this particular series of rigid mol­ecules where there is a fairly limited conformational degree of freedom, all four pairs of crystal structures were analyzed in parallel. The differentiation in NCIs which entails the packing mode of similar mol­ecules is supported by energy calculations based on real or exchanged crystal structures. Our results show that minor structural differences may result in very different supra­molecular inter­actions, and so lead to altered packing modes in the crystalline solids. Even if isostructurality sometimes occurs, the possibility of various mol­ecular packing types cannot be ruled out. On the other hand, isomorphism may just be the result of kinetic possibilities instead of relative thermodynamic stabilities. Though crystal structure prediction is formidable, the com­parison method based on existing crystal structures and quantum calculations can be used to predict the probability of isomorphism. This understanding will help us to design new norbornene derivatives with specified structures.

Computing details

For all structures, data collection: SMART (Bruker, 2000); cell refinement: SMART (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: SHELXTL (Bruker, 2000), PLATON (Spek, 2009), WinGX2014 (Farrugia, 2012), DIAMOND (Brandenburg & Putz, 1999) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015b).

\ (3aR,4S,7R,7aS)-2-Phenyl-3a,4,7,7a-\ tetrahydro-4,7-epoxy-1H-isoindole-1,3(2H)-dione (DNCA-A)

Crystal data

C14H11NO3	F(000) = 504
Mr = 241.24	Dx = 1.428 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.419 (4) Å	Cell parameters from 380 reflections
b = 8.322 (3) Å	θ = 2.5–26.0°
c = 14.342 (6) Å	µ = 0.10 mm^−1
β = 93.612 (6)°	T = 298 K
V = 1121.9 (8) Å^3	Block, colorless
Z = 4	0.37 × 0.31 × 0.20 mm

Data collection

Bruker SMART CCD area detector diffractometer	2498 independent reflections
Radiation source: fine-focus sealed tube	1620 reflections with I > 2σ(I)
Detector resolution: 10.13 pixels mm^-1	Rint = 0.056
phi and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→12
Tmin = 0.976, Tmax = 0.991	k = −10→10
6354 measured reflections	l = −17→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	All H-atom parameters refined
wR(F^2) = 0.119	w = 1/[σ^2(Fo^2) + (0.0598P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.92	(Δ/σ)max < 0.001
2498 reflections	Δρmax = 0.22 e Å^−3
207 parameters	Δρmin = −0.37 e Å^−3

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.

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 > 2sigma(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
C1	1.2306 (2)	0.1220 (2)	0.88484 (14)	0.0432 (5)
C2	1.14269 (19)	0.2622 (2)	0.83934 (12)	0.0364 (4)
C3	1.06189 (19)	0.3229 (2)	0.92097 (12)	0.0373 (5)
C4	1.1133 (2)	0.2008 (2)	0.99827 (13)	0.0432 (5)
C5	1.2662 (2)	0.2435 (3)	1.02428 (15)	0.0509 (5)
C6	1.3382 (2)	0.1953 (3)	0.95473 (15)	0.0495 (5)
C7	1.03048 (19)	0.1956 (2)	0.77127 (12)	0.0380 (4)
C8	0.90755 (19)	0.3013 (2)	0.89211 (12)	0.0369 (4)
C9	0.76820 (18)	0.1594 (2)	0.76295 (12)	0.0348 (4)
C10	0.7349 (2)	0.1809 (2)	0.66837 (13)	0.0404 (5)
C11	0.6142 (2)	0.1096 (3)	0.62805 (15)	0.0490 (5)
C12	0.5270 (2)	0.0191 (3)	0.68042 (16)	0.0532 (6)
C13	0.5606 (2)	−0.0009 (3)	0.77439 (17)	0.0524 (6)
C14	0.6814 (2)	0.0693 (2)	0.81635 (15)	0.0431 (5)
N1	0.89732 (15)	0.22295 (18)	0.80558 (9)	0.0359 (4)
O1	1.12796 (14)	0.05692 (15)	0.94413 (9)	0.0466 (4)
O2	1.04890 (14)	0.12507 (19)	0.69955 (9)	0.0559 (4)
O3	0.80753 (14)	0.34008 (17)	0.93462 (9)	0.0527 (4)
H1	1.2612 (19)	0.040 (2)	0.8401 (12)	0.045 (5)*
H2	1.1997 (18)	0.341 (2)	0.8103 (11)	0.032 (5)*
H3	1.0782 (18)	0.430 (2)	0.9383 (12)	0.042 (5)*
H4	1.0499 (19)	0.187 (2)	1.0489 (13)	0.045 (5)*
H5	1.293 (2)	0.305 (3)	1.0770 (16)	0.076 (8)*
H6	1.440 (2)	0.210 (3)	0.9424 (14)	0.063 (6)*
H10	0.7988 (19)	0.244 (2)	0.6321 (12)	0.043 (5)*
H11	0.594 (2)	0.118 (3)	0.5633 (15)	0.057 (6)*
H12	0.443 (3)	−0.036 (3)	0.6498 (15)	0.071 (7)*
H13	0.497 (2)	−0.065 (3)	0.8105 (13)	0.056 (6)*
H14	0.706 (2)	0.057 (2)	0.8824 (14)	0.055 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0384 (11)	0.0388 (11)	0.0525 (12)	−0.0012 (9)	0.0045 (9)	−0.0031 (10)
C2	0.0380 (10)	0.0349 (10)	0.0365 (10)	−0.0066 (8)	0.0032 (8)	0.0002 (8)
C3	0.0435 (11)	0.0301 (11)	0.0380 (10)	−0.0022 (8)	−0.0004 (8)	−0.0064 (8)
C4	0.0465 (12)	0.0472 (12)	0.0358 (10)	−0.0047 (9)	0.0018 (9)	0.0008 (9)
C5	0.0542 (13)	0.0528 (14)	0.0439 (12)	−0.0076 (11)	−0.0116 (10)	0.0040 (11)
C6	0.0402 (12)	0.0519 (13)	0.0551 (13)	−0.0041 (10)	−0.0058 (10)	0.0081 (10)
C7	0.0407 (11)	0.0401 (11)	0.0336 (10)	−0.0031 (8)	0.0053 (8)	−0.0024 (8)
C8	0.0436 (11)	0.0341 (10)	0.0328 (9)	0.0050 (8)	0.0018 (8)	−0.0041 (8)
C9	0.0340 (10)	0.0313 (10)	0.0387 (10)	0.0037 (8)	0.0003 (8)	−0.0048 (8)
C10	0.0449 (11)	0.0366 (11)	0.0392 (11)	0.0052 (9)	−0.0006 (9)	0.0012 (8)
C11	0.0469 (12)	0.0507 (13)	0.0470 (13)	0.0110 (10)	−0.0163 (10)	−0.0055 (10)
C12	0.0350 (11)	0.0502 (13)	0.0726 (15)	0.0064 (10)	−0.0111 (11)	−0.0112 (12)
C13	0.0397 (12)	0.0456 (12)	0.0727 (15)	−0.0011 (9)	0.0089 (11)	0.0015 (12)
C14	0.0417 (11)	0.0454 (12)	0.0422 (12)	0.0016 (9)	0.0032 (9)	0.0001 (9)
N1	0.0364 (8)	0.0391 (9)	0.0322 (8)	−0.0008 (7)	0.0023 (6)	−0.0066 (7)
O1	0.0474 (8)	0.0348 (8)	0.0575 (8)	−0.0069 (6)	0.0030 (6)	0.0060 (6)
O2	0.0486 (9)	0.0772 (11)	0.0426 (8)	−0.0045 (7)	0.0074 (6)	−0.0219 (8)
O3	0.0488 (9)	0.0623 (10)	0.0477 (8)	0.0086 (7)	0.0075 (7)	−0.0161 (7)

Geometric parameters (Å, º)

C1—O1	1.433 (2)	C7—O2	1.206 (2)
C1—C6	1.509 (3)	C7—N1	1.394 (2)
C1—C2	1.551 (3)	C8—O3	1.198 (2)
C1—H1	0.990 (19)	C8—N1	1.400 (2)
C2—C7	1.499 (3)	C9—C14	1.377 (3)
C2—C3	1.522 (2)	C9—C10	1.384 (3)
C2—H2	0.960 (18)	C9—N1	1.428 (2)
C3—C8	1.497 (3)	C10—C11	1.377 (3)
C3—C4	1.558 (3)	C10—H10	0.972 (19)
C3—H3	0.93 (2)	C11—C12	1.372 (3)
C4—O1	1.438 (2)	C11—H11	0.94 (2)
C4—C5	1.507 (3)	C12—C13	1.375 (3)
C4—H4	0.976 (17)	C12—H12	0.99 (2)
C5—C6	1.304 (3)	C13—C14	1.383 (3)
C5—H5	0.93 (2)	C13—H13	0.97 (2)
C6—H6	0.99 (2)	C14—H14	0.97 (2)
O1—C1—C6	102.04 (16)	C1—C6—H6	123.0 (12)
O1—C1—C2	99.89 (14)	O2—C7—N1	124.13 (17)
C6—C1—C2	107.10 (17)	O2—C7—C2	127.00 (17)
O1—C1—H1	111.1 (10)	N1—C7—C2	108.83 (15)
C6—C1—H1	119.8 (11)	O3—C8—N1	124.35 (17)
C2—C1—H1	114.5 (10)	O3—C8—C3	127.44 (17)
C7—C2—C3	104.91 (15)	N1—C8—C3	108.20 (15)
C7—C2—C1	109.36 (16)	C14—C9—C10	120.64 (18)
C3—C2—C1	101.85 (15)	C14—C9—N1	118.88 (17)
C7—C2—H2	111.2 (10)	C10—C9—N1	120.38 (16)
C3—C2—H2	115.2 (10)	C11—C10—C9	119.0 (2)
C1—C2—H2	113.6 (10)	C11—C10—H10	122.0 (10)
C8—C3—C2	105.75 (15)	C9—C10—H10	119.0 (11)
C8—C3—C4	111.81 (15)	C12—C11—C10	120.9 (2)
C2—C3—C4	100.55 (15)	C12—C11—H11	119.1 (13)
C8—C3—H3	109.2 (11)	C10—C11—H11	119.9 (13)
C2—C3—H3	116.0 (11)	C11—C12—C13	119.6 (2)
C4—C3—H3	113.1 (11)	C11—C12—H12	119.9 (12)
O1—C4—C5	101.97 (16)	C13—C12—H12	120.4 (12)
O1—C4—C3	101.23 (14)	C12—C13—C14	120.5 (2)
C5—C4—C3	105.75 (16)	C12—C13—H13	118.4 (12)
O1—C4—H4	112.7 (11)	C14—C13—H13	121.1 (12)
C5—C4—H4	117.7 (11)	C9—C14—C13	119.3 (2)
C3—C4—H4	115.5 (11)	C9—C14—H14	119.3 (12)
C6—C5—C4	105.83 (19)	C13—C14—H14	121.4 (12)
C6—C5—H5	131.1 (14)	C7—N1—C8	112.06 (15)
C4—C5—H5	122.6 (14)	C7—N1—C9	123.31 (14)
C5—C6—C1	105.82 (19)	C8—N1—C9	124.15 (14)
C5—C6—H6	130.9 (12)	C1—O1—C4	95.56 (14)

\ (3aR,4S,7R,7aS)-2-(4-Nitrophenyl)-3a,4,7,7a-\ tetrahydro-4,7-epoxy-1H-isoindole-1,3(2H)-dione (DNCA-NA)

Crystal data

C14H10N2O5	F(000) = 296
Mr = 286.24	Dx = 1.481 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.285 (3) Å	Cell parameters from 380 reflections
b = 18.418 (9) Å	θ = 2.5–26.0°
c = 6.699 (3) Å	µ = 0.12 mm^−1
β = 100.105 (7)°	T = 298 K
V = 642.0 (6) Å^3	Block, colorless
Z = 2	0.33 × 0.28 × 0.18 mm

Data collection

Bruker SMART CCD area detector diffractometer	2191 independent reflections
Radiation source: fine-focus sealed tube	1541 reflections with I > 2σ(I)
Detector resolution: 10.13 pixels mm^-1	Rint = 0.051
phi and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→5
Tmin = 0.976, Tmax = 0.991	k = −19→23
3815 measured reflections	l = −8→8

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	Only H-atom displacement parameters refined
R[F^2 > 2σ(F^2)] = 0.067	w = 1/[σ^2(Fo^2) + (0.102P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.168	(Δ/σ)max < 0.001
S = 0.97	Δρmax = 0.32 e Å^−3
2191 reflections	Δρmin = −0.36 e Å^−3
224 parameters	Absolute structure: Flack x determined using 381 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.4 (10)

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.

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 > 2sigma(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
C1	0.3179 (11)	0.3910 (3)	0.0715 (10)	0.0508 (14)
C2	0.5903 (10)	0.4140 (3)	0.0360 (8)	0.0409 (12)
C3	0.5217 (9)	0.4617 (3)	−0.1547 (7)	0.0408 (11)
C4	0.2286 (10)	0.4538 (3)	−0.2019 (8)	0.0479 (12)
C5	0.1666 (11)	0.3760 (3)	−0.2614 (10)	0.0643 (17)
H5	0.102698	0.358733	−0.390942	0.08 (2)*
C6	0.2202 (11)	0.3377 (3)	−0.0959 (9)	0.0568 (16)
H6	0.202080	0.287734	−0.083342	0.059 (17)*
C7	0.7219 (9)	0.4641 (3)	0.1978 (8)	0.0467 (12)
C8	0.6040 (9)	0.5366 (3)	−0.0860 (7)	0.0416 (11)
C9	0.8574 (9)	0.5930 (3)	0.2274 (7)	0.0422 (12)
C10	0.7976 (11)	0.6095 (3)	0.4159 (8)	0.0517 (14)
C11	0.9424 (13)	0.6614 (3)	0.5333 (10)	0.0584 (16)
C12	1.1333 (12)	0.6955 (3)	0.4603 (10)	0.0571 (15)
C13	1.1917 (12)	0.6809 (3)	0.2715 (11)	0.0584 (15)
C14	1.0504 (11)	0.6282 (3)	0.1545 (9)	0.0514 (13)
N1	0.7245 (8)	0.5338 (2)	0.1175 (6)	0.0412 (9)
N2	1.2952 (15)	0.7485 (3)	0.5922 (13)	0.087 (2)
O1	0.1724 (7)	0.4551 (2)	0.0023 (6)	0.0528 (10)
O2	0.8097 (9)	0.4487 (3)	0.3704 (6)	0.0730 (14)
O3	0.5735 (9)	0.5923 (2)	−0.1820 (5)	0.0628 (11)
O4	1.2474 (15)	0.7575 (3)	0.7650 (11)	0.119 (3)
O5	1.4660 (14)	0.7777 (4)	0.5304 (12)	0.120 (2)
H1	0.292 (11)	0.382 (3)	0.208 (10)	0.053 (16)*
H2	0.684 (10)	0.374 (3)	0.030 (8)	0.043 (15)*
H3	0.600 (9)	0.450 (3)	−0.266 (7)	0.027 (10)*
H4	0.149 (10)	0.496 (3)	−0.284 (7)	0.039 (13)*
H10	0.663 (12)	0.585 (4)	0.462 (9)	0.055 (16)*
H11	0.886 (12)	0.670 (3)	0.644 (10)	0.054 (17)*
H13	1.323 (13)	0.701 (4)	0.226 (9)	0.061 (18)*
H14	1.108 (12)	0.620 (3)	0.029 (9)	0.057 (17)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.053 (3)	0.050 (3)	0.048 (3)	−0.005 (2)	0.007 (3)	0.004 (2)
C2	0.043 (3)	0.034 (3)	0.042 (3)	0.003 (2)	−0.003 (2)	0.004 (2)
C3	0.044 (3)	0.047 (3)	0.032 (2)	0.004 (2)	0.009 (2)	0.001 (2)
C4	0.048 (3)	0.050 (3)	0.041 (3)	0.004 (2)	−0.004 (2)	0.003 (3)
C5	0.057 (3)	0.061 (4)	0.065 (4)	−0.005 (3)	−0.018 (3)	−0.011 (3)
C6	0.050 (3)	0.049 (3)	0.065 (4)	−0.008 (2)	−0.009 (3)	0.001 (3)
C7	0.045 (3)	0.051 (3)	0.041 (3)	0.005 (2)	−0.004 (2)	0.006 (2)
C8	0.041 (3)	0.055 (3)	0.030 (2)	0.002 (2)	0.0085 (19)	0.005 (2)
C9	0.045 (3)	0.042 (3)	0.037 (3)	0.005 (2)	0.001 (2)	0.003 (2)
C10	0.059 (3)	0.055 (4)	0.041 (3)	0.001 (3)	0.009 (3)	0.004 (3)
C11	0.077 (4)	0.056 (4)	0.041 (3)	0.007 (3)	0.007 (3)	−0.009 (3)
C12	0.063 (4)	0.041 (3)	0.061 (4)	0.005 (2)	−0.007 (3)	−0.008 (3)
C13	0.059 (4)	0.042 (3)	0.074 (4)	−0.006 (3)	0.010 (3)	0.001 (3)
C14	0.058 (3)	0.051 (3)	0.047 (3)	0.000 (3)	0.013 (3)	0.001 (3)
N1	0.046 (2)	0.044 (2)	0.0327 (19)	0.0019 (18)	0.0031 (17)	0.0003 (19)
N2	0.084 (4)	0.054 (4)	0.114 (6)	−0.001 (3)	−0.008 (4)	−0.020 (4)
O1	0.046 (2)	0.058 (2)	0.056 (2)	0.0049 (17)	0.0126 (17)	0.0003 (19)
O2	0.101 (3)	0.059 (3)	0.046 (2)	−0.010 (2)	−0.024 (2)	0.0123 (19)
O3	0.086 (3)	0.057 (2)	0.042 (2)	−0.008 (2)	0.0018 (19)	0.0139 (19)
O4	0.176 (7)	0.084 (4)	0.089 (4)	−0.024 (4)	0.001 (4)	−0.042 (4)
O5	0.109 (5)	0.097 (4)	0.149 (6)	−0.040 (4)	0.014 (4)	−0.058 (4)

Geometric parameters (Å, º)

C1—O1	1.441 (7)	C7—N1	1.393 (7)
C1—C6	1.512 (8)	C8—O3	1.205 (6)
C1—C2	1.558 (8)	C8—N1	1.401 (6)
C1—H1	0.96 (6)	C9—C14	1.369 (8)
C2—C7	1.499 (7)	C9—C10	1.388 (7)
C2—C3	1.540 (7)	C9—N1	1.430 (6)
C2—H2	0.89 (6)	C10—C11	1.380 (9)
C3—C8	1.495 (8)	C10—H10	0.94 (7)
C3—C4	1.532 (7)	C11—C12	1.351 (10)
C3—H3	0.94 (5)	C11—H11	0.86 (7)
C4—O1	1.450 (7)	C12—C13	1.380 (9)
C4—C5	1.508 (9)	C12—N2	1.484 (8)
C4—H4	1.00 (5)	C13—C14	1.381 (9)
C5—C6	1.303 (9)	C13—H13	0.89 (7)
C5—H5	0.9300	C14—H14	0.95 (6)
C6—H6	0.9300	N2—O5	1.186 (9)
C7—O2	1.202 (6)	N2—O4	1.238 (10)
O1—C1—C6	101.6 (4)	O2—C7—C2	127.1 (5)
O1—C1—C2	100.6 (4)	N1—C7—C2	108.8 (4)
C6—C1—C2	105.5 (5)	O3—C8—N1	123.1 (5)
O1—C1—H1	107 (4)	O3—C8—C3	128.0 (4)
C6—C1—H1	120 (3)	N1—C8—C3	108.9 (4)
C2—C1—H1	119 (3)	C14—C9—C10	121.6 (5)
C7—C2—C3	105.1 (4)	C14—C9—N1	120.5 (5)
C7—C2—C1	112.4 (5)	C10—C9—N1	117.8 (5)
C3—C2—C1	101.1 (4)	C11—C10—C9	118.5 (6)
C7—C2—H2	110 (3)	C11—C10—H10	121 (4)
C3—C2—H2	119 (3)	C9—C10—H10	120 (4)
C1—C2—H2	109 (3)	C12—C11—C10	119.4 (6)
C8—C3—C4	112.4 (4)	C12—C11—H11	128 (4)
C8—C3—C2	104.9 (4)	C10—C11—H11	112 (4)
C4—C3—C2	101.5 (4)	C11—C12—C13	122.8 (6)
C8—C3—H3	108 (3)	C11—C12—N2	118.7 (6)
C4—C3—H3	113 (3)	C13—C12—N2	118.4 (7)
C2—C3—H3	117 (3)	C12—C13—C14	118.2 (6)
O1—C4—C5	101.2 (5)	C12—C13—H13	123 (4)
O1—C4—C3	99.8 (4)	C14—C13—H13	118 (4)
C5—C4—C3	108.0 (5)	C9—C14—C13	119.5 (6)
O1—C4—H4	112 (3)	C9—C14—H14	127 (4)
C5—C4—H4	123 (3)	C13—C14—H14	113 (4)
C3—C4—H4	111 (3)	C7—N1—C8	112.1 (4)
C6—C5—C4	106.6 (5)	C7—N1—C9	122.8 (4)
C6—C5—H5	126.7	C8—N1—C9	124.8 (4)
C4—C5—H5	126.7	O5—N2—O4	123.9 (7)
C5—C6—C1	105.9 (5)	O5—N2—C12	119.0 (8)
C5—C6—H6	127.0	O4—N2—C12	117.0 (8)
C1—C6—H6	127.0	C1—O1—C4	96.0 (4)
O2—C7—N1	124.1 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O4^i	0.89 (6)	2.55 (6)	3.228 (8)	134 (4)
C10—H10···O3^ii	0.94 (7)	2.51 (6)	3.143 (8)	124 (5)

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

(3aR,4S,7R,7aS)-2-(4-nitrophenyl)-3a,4,5,6,7,7a-hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione (NCA-NA)

Crystal data

C14H12N2O5	F(000) = 300
Mr = 288.26	Dx = 1.467 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54184 Å
a = 5.3661 (4) Å	Cell parameters from 380 reflections
b = 18.6171 (16) Å	θ = 2.5–26.0°
c = 6.6116 (5) Å	µ = 0.96 mm^−1
β = 98.918 (7)°	T = 293 K
V = 652.52 (9) Å^3	Plate, light yellow
Z = 2	0.33 × 0.30 × 0.12 mm

Data collection

Bruker SMART CCD area detector diffractometer	1717 independent reflections
Radiation source: fine-focus sealed tube	1549 reflections with I > 2σ(I)
Detector resolution: 10.12 pixels mm^-1	Rint = 0.022
phi and ω scans	θmax = 71.4°, θmin = 4.8°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −6→5
Tmin = 0.070, Tmax = 0.080	k = −22→22
2121 measured reflections	l = −7→8

Refinement

Refinement on F^2	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0546P)^2 + 0.0162P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.040	(Δ/σ)max < 0.001
wR(F^2) = 0.109	Δρmax = 0.18 e Å^−3
S = 1.06	Δρmin = −0.16 e Å^−3
1717 reflections	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
239 parameters	Extinction coefficient: 0.0126 (19)
1 restraint	Absolute structure: Flack x determined using 354 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: difference Fourier map	Absolute structure parameter: 0.5 (3)

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.

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 > 2sigma(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
C1	0.2048 (7)	−0.0320 (2)	0.3085 (6)	0.0522 (9)
C2	0.4905 (6)	−0.0221 (2)	0.3598 (5)	0.0462 (8)
C3	0.5522 (6)	−0.0685 (2)	0.5521 (6)	0.0463 (8)
C4	0.2911 (7)	−0.0940 (2)	0.5848 (6)	0.0511 (9)
C5	0.2009 (9)	−0.1524 (3)	0.4287 (7)	0.0614 (11)
C6	0.1478 (10)	−0.1092 (3)	0.2305 (7)	0.0623 (11)
C7	0.5688 (6)	0.0531 (2)	0.4279 (5)	0.0450 (8)
C8	0.6741 (7)	−0.0186 (2)	0.7166 (6)	0.0506 (9)
C9	0.8205 (7)	0.1075 (2)	0.7397 (5)	0.0462 (8)
C10	1.0152 (7)	0.1396 (2)	0.6584 (6)	0.0537 (9)
C11	1.1593 (8)	0.1921 (2)	0.7694 (8)	0.0600 (11)
C12	1.1059 (8)	0.2092 (2)	0.9628 (7)	0.0569 (10)
C13	0.9130 (8)	0.1787 (2)	1.0427 (7)	0.0572 (10)
C14	0.7661 (8)	0.1270 (2)	0.9291 (6)	0.0527 (9)
N1	0.6843 (5)	0.05002 (18)	0.6321 (4)	0.0439 (6)
N2	1.2669 (9)	0.2618 (2)	1.0877 (9)	0.0792 (13)
O1	0.1353 (4)	−0.03368 (16)	0.5106 (4)	0.0554 (7)
O2	0.5347 (6)	0.10763 (18)	0.3318 (4)	0.0652 (8)
O3	0.7507 (7)	−0.0326 (2)	0.8918 (4)	0.0778 (10)
O4	1.4352 (8)	0.2897 (2)	1.0136 (9)	0.1062 (15)
O5	1.2275 (10)	0.2727 (3)	1.2621 (8)	0.1155 (18)
H1	0.116 (8)	0.007 (3)	0.230 (7)	0.054 (11)*
H2	0.580 (7)	−0.033 (2)	0.258 (6)	0.047 (10)*
H3	0.647 (8)	−0.107 (2)	0.537 (6)	0.052 (11)*
H4	0.280 (8)	−0.103 (3)	0.724 (7)	0.062 (13)*
H5A	0.042 (10)	−0.175 (3)	0.460 (8)	0.077 (15)*
H5B	0.320 (9)	−0.184 (3)	0.429 (7)	0.064 (13)*
H6A	−0.008 (13)	−0.112 (3)	0.170 (9)	0.10 (2)*
H6B	0.269 (10)	−0.123 (3)	0.136 (9)	0.082 (16)*
H10	1.061 (7)	0.128 (2)	0.526 (6)	0.046 (10)*
H11	1.282 (10)	0.214 (3)	0.713 (8)	0.077 (16)*
H13	0.895 (9)	0.192 (3)	1.177 (8)	0.064 (14)*
H14	0.641 (8)	0.102 (2)	0.992 (6)	0.047 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0469 (17)	0.053 (2)	0.0524 (19)	0.0052 (17)	−0.0061 (15)	−0.0012 (18)
C2	0.0426 (16)	0.060 (2)	0.0371 (16)	0.0046 (16)	0.0090 (13)	−0.0020 (16)
C3	0.0420 (16)	0.048 (2)	0.0478 (19)	0.0066 (15)	0.0035 (14)	0.0036 (16)
C4	0.0517 (19)	0.052 (2)	0.049 (2)	−0.0032 (17)	0.0056 (16)	0.0003 (17)
C5	0.054 (2)	0.055 (2)	0.073 (3)	−0.004 (2)	0.002 (2)	−0.005 (2)
C6	0.060 (2)	0.061 (2)	0.061 (2)	0.003 (2)	−0.010 (2)	−0.010 (2)
C7	0.0419 (16)	0.056 (2)	0.0389 (15)	−0.0007 (17)	0.0106 (13)	0.0040 (17)
C8	0.0452 (17)	0.053 (2)	0.0504 (19)	0.0027 (17)	−0.0016 (14)	0.0090 (18)
C9	0.0477 (18)	0.0430 (18)	0.0468 (17)	0.0039 (15)	0.0035 (15)	0.0066 (16)
C10	0.0510 (19)	0.053 (2)	0.059 (2)	0.0016 (18)	0.0128 (17)	0.0036 (19)
C11	0.0492 (19)	0.046 (2)	0.085 (3)	−0.0008 (18)	0.011 (2)	0.005 (2)
C12	0.054 (2)	0.043 (2)	0.068 (3)	0.0050 (17)	−0.0058 (19)	−0.0033 (18)
C13	0.060 (2)	0.055 (2)	0.054 (2)	0.0036 (19)	0.0016 (18)	−0.0042 (19)
C14	0.054 (2)	0.056 (2)	0.0483 (19)	−0.0023 (18)	0.0076 (16)	0.0044 (18)
N1	0.0441 (14)	0.0470 (15)	0.0395 (13)	−0.0007 (14)	0.0028 (11)	0.0053 (14)
N2	0.066 (2)	0.048 (2)	0.118 (4)	0.0001 (19)	−0.003 (2)	−0.014 (2)
O1	0.0432 (12)	0.0569 (15)	0.0671 (16)	0.0020 (12)	0.0113 (11)	−0.0072 (14)
O2	0.084 (2)	0.0622 (17)	0.0470 (14)	−0.0069 (16)	0.0018 (13)	0.0164 (14)
O3	0.107 (2)	0.0626 (19)	0.0518 (15)	−0.011 (2)	−0.0247 (15)	0.0169 (14)
O4	0.077 (2)	0.073 (2)	0.167 (4)	−0.024 (2)	0.012 (3)	−0.036 (3)
O5	0.131 (4)	0.101 (3)	0.110 (3)	−0.026 (3)	0.003 (3)	−0.056 (3)

Geometric parameters (Å, º)

C1—O1	1.442 (5)	C7—O2	1.197 (5)
C1—C2	1.529 (5)	C7—N1	1.397 (4)
C1—C6	1.540 (6)	C8—O3	1.197 (4)
C1—H1	0.98 (5)	C8—N1	1.399 (5)
C2—C7	1.510 (6)	C9—C14	1.378 (5)
C2—C3	1.530 (5)	C9—C10	1.383 (5)
C2—H2	0.91 (4)	C9—N1	1.422 (5)
C3—C8	1.501 (5)	C10—C11	1.385 (6)
C3—C4	1.526 (5)	C10—H10	0.97 (4)
C3—H3	0.90 (5)	C11—C12	1.390 (7)
C4—O1	1.440 (5)	C11—H11	0.90 (6)
C4—C5	1.525 (6)	C12—C13	1.358 (6)
C4—H4	0.94 (5)	C12—N2	1.471 (6)
C5—C6	1.527 (7)	C13—C14	1.389 (6)
C5—H5A	1.00 (5)	C13—H13	0.94 (5)
C5—H5B	0.87 (5)	C14—H14	0.97 (4)
C6—H6A	0.87 (7)	N2—O4	1.209 (7)
C6—H6B	1.00 (6)	N2—O5	1.221 (7)
O1—C1—C2	101.1 (3)	C1—C6—H6B	110 (3)
O1—C1—C6	102.9 (4)	H6A—C6—H6B	112 (5)
C2—C1—C6	109.1 (4)	O2—C7—N1	123.8 (4)
O1—C1—H1	109 (3)	O2—C7—C2	128.0 (3)
C2—C1—H1	115 (3)	N1—C7—C2	108.2 (3)
C6—C1—H1	118 (3)	O3—C8—N1	123.9 (4)
C7—C2—C1	113.6 (3)	O3—C8—C3	127.7 (4)
C7—C2—C3	105.1 (3)	N1—C8—C3	108.4 (3)
C1—C2—C3	101.3 (3)	C14—C9—C10	121.2 (4)
C7—C2—H2	106 (3)	C14—C9—N1	119.2 (3)
C1—C2—H2	116 (2)	C10—C9—N1	119.4 (3)
C3—C2—H2	115 (3)	C9—C10—C11	119.5 (4)
C8—C3—C4	113.4 (3)	C9—C10—H10	125 (2)
C8—C3—C2	105.5 (3)	C11—C10—H10	116 (2)
C4—C3—C2	102.0 (3)	C10—C11—C12	118.2 (4)
C8—C3—H3	113 (3)	C10—C11—H11	119 (4)
C4—C3—H3	108 (3)	C12—C11—H11	123 (4)
C2—C3—H3	114 (3)	C13—C12—C11	122.7 (4)
O1—C4—C5	102.6 (3)	C13—C12—N2	118.4 (4)
O1—C4—C3	101.9 (3)	C11—C12—N2	118.8 (4)
C5—C4—C3	109.1 (3)	C12—C13—C14	118.8 (4)
O1—C4—H4	110 (3)	C12—C13—H13	117 (3)
C5—C4—H4	118 (3)	C14—C13—H13	124 (3)
C3—C4—H4	113 (3)	C9—C14—C13	119.5 (4)
C4—C5—C6	101.7 (4)	C9—C14—H14	121 (3)
C4—C5—H5A	111 (3)	C13—C14—H14	119 (2)
C6—C5—H5A	110 (3)	C7—N1—C8	112.6 (3)
C4—C5—H5B	109 (3)	C7—N1—C9	124.7 (3)
C6—C5—H5B	114 (3)	C8—N1—C9	122.4 (3)
H5A—C5—H5B	111 (4)	O4—N2—O5	124.1 (5)
C5—C6—C1	101.7 (3)	O4—N2—C12	118.0 (5)
C5—C6—H6A	113 (4)	O5—N2—C12	117.9 (5)
C1—C6—H6A	110 (4)	C4—O1—C1	96.5 (3)
C5—C6—H6B	110 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O3^i	0.87 (7)	2.55 (7)	3.179 (6)	130 (5)
C6—H6B···O4^ii	1.00 (6)	2.57 (6)	3.504 (7)	154 (5)
C14—H14···O2^iii	0.97 (4)	2.40 (4)	3.128 (5)	131 (3)
C13—H13···O5	0.94 (5)	2.33 (5)	2.693 (6)	102 (3)

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

(3aR,4S,7R,7aS)-2-(2-Hydroxyethyl)-3a,4,5,6,7,7a-hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione (NCA-AE)

Crystal data

C10H13NO4	Dx = 1.394 Mg m^−3
Mr = 211.21	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pmn21	Cell parameters from 380 reflections
a = 10.0350 (17) Å	θ = 2.5–26.0°
b = 5.5937 (13) Å	µ = 0.91 mm^−1
c = 8.9634 (17) Å	T = 293 K
V = 503.14 (17) Å^3	Plate, colorless
Z = 2	0.38 × 0.35 × 0.12 mm
F(000) = 224

Data collection

Bruker SMART CCD area detector diffractometer	731 independent reflections
Radiation source: fine-focus sealed tube	594 reflections with I > 2σ(I)
Detector resolution: 10.12 pixels mm^-1	Rint = 0.027
phi and ω scans	θmax = 71.7°, θmin = 6.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −12→8
Tmin = 0.719, Tmax = 0.885	k = −6→6
1569 measured reflections	l = −10→11

Refinement

Refinement on F^2	Only H-atom displacement parameters refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0317P)^2 + 0.0793P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.045	(Δ/σ)max < 0.001
wR(F^2) = 0.099	Δρmax = 0.14 e Å^−3
S = 1.07	Δρmin = −0.12 e Å^−3
731 reflections	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
113 parameters	Extinction coefficient: 0.0122 (19)
4 restraints	Absolute structure: Flack x determined using 120 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: mixed	Absolute structure parameter: 0.6 (6)

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.

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 > 2sigma(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	Occ. (<1)
C1	0.0762 (5)	0.5419 (9)	0.3893 (5)	0.0636 (13)
C2	0.1072 (4)	0.5946 (8)	0.5513 (5)	0.0544 (12)
C3	0.0763 (3)	0.8593 (7)	0.5839 (4)	0.0454 (10)
C4	0.1143 (4)	0.9308 (7)	0.7394 (5)	0.0498 (10)
C5	0.000000	1.0237 (13)	0.9811 (8)	0.067 (2)
C6	−0.028 (3)	1.289 (2)	1.0039 (12)	0.080 (10)	0.5
N1	0.000000	0.9642 (8)	0.8213 (5)	0.0478 (12)
O1	0.000000	0.4758 (7)	0.6294 (5)	0.0588 (12)
O2	0.2271 (3)	0.9512 (6)	0.7872 (5)	0.0842 (13)
O3	0.0717 (9)	1.4328 (12)	0.9424 (10)	0.076 (2)	0.5
H7	0.096057	1.384427	0.860506	0.29 (16)*	0.5
H1A	0.113 (5)	0.393 (10)	0.360 (6)	0.081 (16)*
H1B	0.121 (4)	0.655 (8)	0.316 (6)	0.070 (13)*
H2	0.198 (5)	0.538 (8)	0.591 (6)	0.084 (16)*
H3	0.121 (4)	0.960 (7)	0.520 (6)	0.055 (12)*
H5	0.086 (5)	0.951 (11)	1.037 (8)	0.12 (2)*
H6A	−0.014 (11)	1.307 (13)	1.110 (3)	0.08 (3)*	0.5
H6B	−0.123 (4)	1.29 (2)	0.986 (12)	0.08 (4)*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.083 (3)	0.057 (3)	0.050 (3)	0.005 (2)	0.011 (3)	−0.016 (3)
C2	0.058 (3)	0.054 (2)	0.051 (3)	0.011 (2)	0.001 (2)	−0.005 (2)
C3	0.0441 (19)	0.046 (2)	0.046 (2)	−0.0034 (16)	0.0037 (19)	−0.003 (2)
C4	0.051 (2)	0.046 (2)	0.052 (2)	0.0005 (16)	−0.007 (2)	−0.0077 (19)
C5	0.092 (5)	0.067 (5)	0.042 (4)	0.000	0.000	−0.006 (3)
C6	0.11 (3)	0.095 (7)	0.041 (4)	−0.015 (10)	0.008 (7)	−0.031 (5)
N1	0.059 (3)	0.044 (3)	0.040 (3)	0.000	0.000	−0.006 (2)
O1	0.085 (3)	0.044 (2)	0.047 (2)	0.000	0.000	0.001 (2)
O2	0.0531 (19)	0.108 (3)	0.091 (3)	0.0125 (15)	−0.0223 (19)	−0.038 (2)
O3	0.097 (5)	0.060 (4)	0.070 (5)	−0.009 (4)	−0.008 (4)	0.003 (4)

Geometric parameters (Å, º)

C1—C2	1.514 (7)	C5—N1	1.470 (8)
C1—C1^i	1.530 (10)	C5—C6^i	1.523 (15)
C1—H1A	0.95 (6)	C5—C6	1.523 (15)
C1—H1B	1.02 (5)	C5—H5	1.08 (5)
C2—O1	1.445 (5)	C6—C6^i	0.57 (6)
C2—C3	1.540 (5)	C6—O3^i	1.069 (16)
C2—H2	1.03 (5)	C6—O3	1.40 (2)
C3—C4	1.500 (6)	C6—H6A	0.966 (13)
C3—C3^i	1.532 (7)	C6—H6B	0.962 (13)
C3—H3	0.92 (5)	O3—O3^i	1.439 (18)
C4—O2	1.215 (5)	O3—H7	0.8200
C4—N1	1.374 (5)
C2—C1—C1^i	101.8 (3)	C6—C5—H5	117 (4)
C2—C1—H1A	111 (3)	C6^i—C6—O3^i	114.0 (14)
C1^i—C1—H1A	113 (3)	C6^i—C6—O3	44.2 (10)
C2—C1—H1B	114 (3)	O3^i—C6—O3	69.8 (12)
C1^i—C1—H1B	116 (3)	C6^i—C6—C5	79.2 (10)
H1A—C1—H1B	101 (4)	O3^i—C6—C5	137.8 (11)
O1—C2—C1	102.8 (4)	O3—C6—C5	111.9 (16)
O1—C2—C3	101.6 (3)	C6^i—C6—H6A	81 (7)
C1—C2—C3	109.1 (4)	O3^i—C6—H6A	119 (5)
O1—C2—H2	110 (3)	O3—C6—H6A	103 (6)
C1—C2—H2	117 (3)	C5—C6—H6A	102 (5)
C3—C2—H2	114 (3)	C6^i—C6—H6B	170 (7)
C4—C3—C3^i	104.7 (2)	O3^i—C6—H6B	60 (7)
C4—C3—C2	112.4 (3)	O3—C6—H6B	129 (8)
C3^i—C3—C2	101.6 (2)	C5—C6—H6B	100 (7)
C4—C3—H3	107 (3)	H6A—C6—H6B	108 (3)
C3^i—C3—H3	119 (3)	C4—N1—C4^i	113.1 (5)
C2—C3—H3	112 (3)	C4—N1—C5	123.4 (2)
O2—C4—N1	125.2 (4)	C4^i—N1—C5	123.4 (2)
O2—C4—C3	126.1 (4)	C2—O1—C2^i	96.2 (5)
N1—C4—C3	108.7 (3)	C6^i—O3—C6	22 (2)
N1—C5—C6^i	110.6 (7)	C6^i—O3—O3^i	66.0 (14)
N1—C5—C6	110.6 (7)	C6—O3—O3^i	44.2 (10)
C6^i—C5—C6	22 (2)	C6^i—O3—H7	109.5
N1—C5—H5	111 (4)	C6—O3—H7	112.1
C6^i—C5—H5	99 (4)	O3^i—O3—H7	107.3

Symmetry code: (i) −x, y, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H7···O1^ii	0.82	2.34	2.906 (10)	127
C1—H1A···O2^iii	0.95 (6)	2.59 (6)	3.513 (6)	165 (4)
O3—H7···N1	0.82	2.56	2.927 (8)	108

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