3-Hy­droxy-2-phenyl-2,3,3a,7a-tetra­hydro-1H,5H-pyrano[3,2-b]pyrrol-5-one: crystal structure and Hirshfeld surface analysis

Twisted and half-chair conformations are found for the five- and six-membered rings comprising the fused-ring system in the title isoaltholactone derivative. In the mol­ecular packing, linear supra­molecular chains sustained by hy­droxy-O—H...N(amine) hydrogen bonding are evident.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.094
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor       N1     --  H1N    ...     Please Check
PLAT907_ALERT_2_C Flack x > 0.5, Structure needs to be Inverted? .       0.70 Check
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         87 %

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite          4 Note
PLAT032_ALERT_4_G Std. Uncertainty on Flack Parameter Value High .      0.500 Report
PLAT172_ALERT_4_G The CIF-Embedded .res File Contains DFIX Records          2 Report
PLAT791_ALERT_4_G The Model has Chirality at C4      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C5      (Chiral SPGR)          S Verify
PLAT791_ALERT_4_G The Model has Chirality at C6      (Chiral SPGR)          R Verify
PLAT791_ALERT_4_G The Model has Chirality at C7      (Chiral SPGR)          R Verify
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         12 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Note

   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
  10 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
   2 ALERT type 3 Indicator that the structure quality may be low
   7 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.
PUBL022_ALERT_1_A There is a mismatched ~ on line 253
              pair of well-separated spikes with the tips at <i>d</i>~e~ + <i>d</i>~i~ \~
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   2 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, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), QMol (Gans & Shalloway, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

3-Hydroxy-2-phenyl-2,3,3a,7a-tetrahydro-1H,5H-pyrano[3,2-b]pyrrol-5-one

Crystal data

C13H13NO3	F(000) = 244
Mr = 231.24	Dx = 1.388 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.9638 (2) Å	Cell parameters from 2450 reflections
b = 8.4266 (3) Å	θ = 2.4–27.3°
c = 11.0246 (4) Å	µ = 0.10 mm^−1
β = 92.779 (3)°	T = 100 K
V = 553.39 (3) Å^3	Block, colourless
Z = 2	0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART APEXII diffractometer	2377 independent reflections
Radiation source: sealed tube	2149 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→7
Tmin = 0.914, Tmax = 1.000	k = −10→10
4550 measured reflections	l = −14→14

Refinement

Refinement on F^2	H-atom parameters not refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0534P)^2 + 0.049P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.036	(Δ/σ)max < 0.001
wR(F^2) = 0.094	Δρmax = 0.14 e Å^−3
S = 1.03	Δρmin = −0.19 e Å^−3
2377 reflections	Absolute structure: Flack x determined using 856 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013)
160 parameters	Absolute structure parameter: 0.7 (5)
3 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	1.1372 (3)	0.1225 (4)	0.51075 (18)	0.0772 (7)
O2	1.0038 (3)	−0.0413 (2)	0.37308 (15)	0.0519 (5)
O3	1.0370 (3)	0.1267 (2)	0.16741 (16)	0.0474 (4)
H3O	1.171 (3)	0.091 (5)	0.176 (3)	0.071*
N1	0.4839 (3)	−0.0156 (3)	0.18328 (16)	0.0399 (4)
H1N	0.463 (4)	−0.1113 (19)	0.156 (2)	0.048*
C1	0.9838 (4)	0.0886 (4)	0.44096 (19)	0.0497 (6)
C2	0.7749 (4)	0.1800 (3)	0.4292 (2)	0.0499 (6)
H2	0.7692	0.2817	0.4661	0.060*
C3	0.5947 (4)	0.1256 (4)	0.3691 (2)	0.0452 (5)
H3	0.4612	0.1873	0.3664	0.054*
C4	0.5952 (4)	−0.0302 (3)	0.3053 (2)	0.0424 (5)
H4	0.5202	−0.1133	0.3538	0.051*
C5	0.8350 (4)	−0.0795 (3)	0.2802 (2)	0.0427 (5)
H5	0.8361	−0.1971	0.2683	0.051*
C6	0.8844 (3)	−0.0009 (3)	0.15679 (18)	0.0371 (5)
H6	0.9389	−0.0821	0.0990	0.044*
C7	0.6538 (3)	0.0636 (3)	0.11123 (18)	0.0325 (4)
H7	0.6510	0.1788	0.1330	0.039*
C8	0.6046 (3)	0.0531 (3)	−0.02427 (19)	0.0343 (4)
C9	0.3983 (4)	0.0059 (3)	−0.0742 (2)	0.0429 (5)
H9	0.2824	−0.0227	−0.0222	0.051*
C10	0.3576 (4)	−0.0004 (3)	−0.1992 (2)	0.0483 (6)
H10	0.2153	−0.0342	−0.2319	0.058*
C11	0.5227 (4)	0.0422 (3)	−0.2758 (2)	0.0495 (6)
H11	0.4947	0.0384	−0.3614	0.059*
C12	0.7296 (4)	0.0904 (4)	−0.2272 (2)	0.0513 (6)
H12	0.8446	0.1197	−0.2796	0.062*
C13	0.7697 (4)	0.0962 (3)	−0.1027 (2)	0.0457 (6)
H13	0.9122	0.1302	−0.0703	0.055*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0479 (11)	0.130 (2)	0.0521 (10)	0.0000 (13)	−0.0175 (9)	−0.0153 (14)
O2	0.0411 (9)	0.0693 (12)	0.0437 (8)	0.0104 (8)	−0.0133 (7)	0.0077 (9)
O3	0.0286 (7)	0.0602 (10)	0.0528 (9)	−0.0071 (7)	−0.0035 (7)	0.0029 (9)
N1	0.0318 (9)	0.0502 (11)	0.0374 (9)	−0.0081 (9)	−0.0018 (7)	0.0015 (9)
C1	0.0378 (12)	0.0800 (19)	0.0307 (10)	−0.0039 (12)	−0.0044 (9)	0.0034 (12)
C2	0.0434 (13)	0.0707 (17)	0.0356 (11)	0.0002 (12)	0.0022 (10)	−0.0095 (11)
C3	0.0333 (11)	0.0673 (15)	0.0351 (10)	0.0030 (11)	0.0037 (8)	−0.0010 (11)
C4	0.0341 (11)	0.0546 (14)	0.0383 (11)	−0.0068 (10)	−0.0009 (8)	0.0079 (11)
C5	0.0398 (12)	0.0440 (12)	0.0433 (12)	0.0033 (10)	−0.0084 (10)	0.0047 (10)
C6	0.0278 (9)	0.0451 (12)	0.0379 (10)	0.0038 (9)	−0.0027 (8)	−0.0032 (10)
C7	0.0258 (9)	0.0366 (10)	0.0348 (10)	0.0011 (8)	−0.0010 (8)	0.0003 (9)
C8	0.0309 (10)	0.0354 (10)	0.0363 (10)	0.0033 (8)	−0.0025 (9)	0.0000 (8)
C9	0.0322 (10)	0.0561 (14)	0.0400 (11)	−0.0028 (10)	−0.0014 (9)	−0.0019 (11)
C10	0.0391 (11)	0.0620 (15)	0.0426 (12)	−0.0018 (12)	−0.0098 (10)	−0.0040 (12)
C11	0.0535 (14)	0.0582 (14)	0.0363 (11)	0.0033 (12)	−0.0036 (11)	0.0019 (11)
C12	0.0468 (13)	0.0663 (18)	0.0410 (12)	−0.0055 (12)	0.0039 (10)	0.0090 (12)
C13	0.0373 (12)	0.0560 (14)	0.0433 (12)	−0.0076 (10)	−0.0032 (9)	0.0050 (11)

Geometric parameters (Å, º)

O1—C1	1.201 (3)	C5—H5	1.0000
O2—C1	1.334 (4)	C6—C7	1.540 (3)
O2—C5	1.437 (3)	C6—H6	1.0000
O3—C6	1.409 (3)	C7—C8	1.511 (3)
O3—H3O	0.852 (13)	C7—H7	1.0000
N1—C4	1.476 (3)	C8—C9	1.382 (3)
N1—C7	1.477 (3)	C8—C13	1.390 (3)
N1—H1N	0.869 (13)	C9—C10	1.388 (3)
C1—C2	1.465 (4)	C9—H9	0.9500
C2—C3	1.317 (3)	C10—C11	1.376 (4)
C2—H2	0.9500	C10—H10	0.9500
C3—C4	1.490 (4)	C11—C12	1.383 (4)
C3—H3	0.9500	C11—H11	0.9500
C4—C5	1.527 (3)	C12—C13	1.383 (3)
C4—H4	1.0000	C12—H12	0.9500
C5—C6	1.554 (3)	C13—H13	0.9500
C1—O2—C5	120.30 (18)	C7—C6—C5	103.38 (16)
C6—O3—H3O	110 (3)	O3—C6—H6	110.3
C4—N1—C7	103.78 (16)	C7—C6—H6	110.3
C4—N1—H1N	107.0 (17)	C5—C6—H6	110.3
C7—N1—H1N	108.7 (18)	N1—C7—C8	113.57 (17)
O1—C1—O2	117.9 (3)	N1—C7—C6	106.87 (16)
O1—C1—C2	123.3 (3)	C8—C7—C6	115.42 (17)
O2—C1—C2	118.7 (2)	N1—C7—H7	106.8
C3—C2—C1	122.1 (3)	C8—C7—H7	106.8
C3—C2—H2	119.0	C6—C7—H7	106.8
C1—C2—H2	119.0	C9—C8—C13	118.11 (19)
C2—C3—C4	121.6 (2)	C9—C8—C7	122.51 (19)
C2—C3—H3	119.2	C13—C8—C7	119.36 (19)
C4—C3—H3	119.2	C8—C9—C10	121.1 (2)
N1—C4—C3	110.2 (2)	C8—C9—H9	119.5
N1—C4—C5	103.95 (18)	C10—C9—H9	119.5
C3—C4—C5	110.40 (19)	C11—C10—C9	120.3 (2)
N1—C4—H4	110.7	C11—C10—H10	119.9
C3—C4—H4	110.7	C9—C10—H10	119.9
C5—C4—H4	110.7	C10—C11—C12	119.4 (2)
O2—C5—C4	116.09 (19)	C10—C11—H11	120.3
O2—C5—C6	111.85 (19)	C12—C11—H11	120.3
C4—C5—C6	105.18 (17)	C13—C12—C11	120.2 (2)
O2—C5—H5	107.8	C13—C12—H12	119.9
C4—C5—H5	107.8	C11—C12—H12	119.9
C6—C5—H5	107.8	C12—C13—C8	121.0 (2)
O3—C6—C7	108.71 (18)	C12—C13—H13	119.5
O3—C6—C5	113.67 (18)	C8—C13—H13	119.5
C5—O2—C1—O1	−174.2 (2)	C4—N1—C7—C8	164.56 (19)
C5—O2—C1—C2	7.4 (3)	C4—N1—C7—C6	36.1 (2)
O1—C1—C2—C3	−167.4 (3)	O3—C6—C7—N1	−137.08 (18)
O2—C1—C2—C3	10.9 (4)	C5—C6—C7—N1	−16.0 (2)
C1—C2—C3—C4	−2.3 (4)	O3—C6—C7—C8	95.6 (2)
C7—N1—C4—C3	76.7 (2)	C5—C6—C7—C8	−143.36 (19)
C7—N1—C4—C5	−41.6 (2)	N1—C7—C8—C9	13.6 (3)
C2—C3—C4—N1	−135.3 (2)	C6—C7—C8—C9	137.5 (2)
C2—C3—C4—C5	−21.0 (3)	N1—C7—C8—C13	−168.2 (2)
C1—O2—C5—C4	−32.2 (3)	C6—C7—C8—C13	−44.3 (3)
C1—O2—C5—C6	88.5 (3)	C13—C8—C9—C10	0.8 (4)
N1—C4—C5—O2	155.49 (19)	C7—C8—C9—C10	179.1 (2)
C3—C4—C5—O2	37.3 (3)	C8—C9—C10—C11	−0.7 (4)
N1—C4—C5—C6	31.3 (2)	C9—C10—C11—C12	0.3 (4)
C3—C4—C5—C6	−86.9 (2)	C10—C11—C12—C13	−0.2 (4)
O2—C5—C6—O3	−18.5 (3)	C11—C12—C13—C8	0.4 (4)
C4—C5—C6—O3	108.4 (2)	C9—C8—C13—C12	−0.7 (4)
O2—C5—C6—C7	−136.12 (18)	C7—C8—C13—C12	−179.0 (2)
C4—C5—C6—C7	−9.3 (2)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···N1^i	0.86 (2)	2.07 (2)	2.920 (3)	174 (4)
N1—H1N···Cg3^ii	0.87 (1)	2.88 (2)	3.705 (3)	160 (2)
C11—H11···O1^iii	0.95	2.60	3.280 (3)	129

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