Crystal structure and Hirshfeld surface analysis of ethyl (4R,4aS)-2-methyl-5,8-dioxo-6-phenyl-4a,5,6,7,7a,8-hexa­hydro-4H-furo[2,3-f]iso­indole-4-carboxyl­ate

The central six-membered ring of the title compound has a slightly distorted half-chair conformation while the conformation of the fused pyrrolidine ring is that of an envelope. Mol­ecules are connected by inter­molecular C—H...O hydrogen bonds, C—H...π inter­actions and π–π stacking inter­actions, forming a three dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.125
• Data-to-parameter ratio = 22.5

checkCIF/PLATON results

No syntax errors found



Alert level C
CRYSC01_ALERT_1_C No recognised colour has been given for crystal colour.
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.95 Report
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........  <I>CG</I> Check
PLAT717_ALERT_1_C D...A   Unknown or Inconsistent Label ..........  <I>CG</I> Check

Alert level G
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1             106.4 Degree
PLAT793_ALERT_4_G Model has Chirality at C5          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C6          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C9          (Centro SPGR)          R Verify
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         58 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         19 Info

   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
   7 ALERT level G = General information/check it is not something unexpected

   3 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
   1 ALERT type 3 Indicator that the structure quality may be low
   4 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, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); 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); software used to prepare material for publication: PLATON (Spek, 2020).

Ethyl (4R,4aS)-2-methyl-5,8-dioxo-6-phenyl-4a,5,6,7,7a,8-hexahydro-4H-furo[2,3-f]isoindole-4-carboxylate

Crystal data

C20H19NO5	Z = 2
Mr = 353.36	F(000) = 372
Triclinic, P1	Dx = 1.338 Mg m^−3
a = 8.8100 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9182 (16) Å	Cell parameters from 9941 reflections
c = 11.165 (2) Å	θ = 2.6–30.6°
α = 81.205 (7)°	µ = 0.10 mm^−1
β = 70.657 (6)°	T = 120 K
γ = 72.642 (4)°	Prism, light beige
V = 877.0 (3) Å^3	0.2 × 0.2 × 0.2 mm

Data collection

Bruker APEXII CCD diffractometer	5332 independent reflections
Radiation source: sealed tube	4669 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω and φ scans	θmax = 30.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −12→12
Tmin = 0.659, Tmax = 0.746	k = −14→14
19857 measured reflections	l = −15→15

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.125	w = 1/[σ^2(Fo^2) + (0.0747P)^2 + 0.2272P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
5332 reflections	Δρmax = 0.53 e Å^−3
237 parameters	Δρmin = −0.18 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.

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

	x	y	z	Uiso*/Ueq
C1	0.49262 (11)	0.82060 (9)	0.82393 (8)	0.01800 (17)
C2	0.52219 (12)	0.77526 (10)	1.01557 (9)	0.01914 (18)
C3	0.41740 (12)	0.69939 (10)	1.01089 (9)	0.02056 (18)
H3	0.367401	0.639266	1.077116	0.025*
C4	0.39835 (11)	0.72876 (9)	0.88651 (9)	0.01857 (17)
C5	0.29588 (12)	0.68264 (10)	0.82451 (9)	0.02036 (18)
H5	0.297539	0.581687	0.852768	0.024*
C6	0.37337 (12)	0.69298 (10)	0.67917 (9)	0.01928 (17)
H6	0.289113	0.686876	0.639739	0.023*
C7	0.52879 (12)	0.57073 (10)	0.63456 (9)	0.02000 (18)
C8	0.56409 (13)	0.76769 (10)	0.49121 (9)	0.02031 (18)
H8A	0.508910	0.774189	0.425593	0.024*
H8B	0.650611	0.820227	0.458834	0.024*
C9	0.43715 (12)	0.82351 (9)	0.61653 (9)	0.01886 (17)
H9	0.343898	0.902634	0.599506	0.023*
C10	0.52459 (12)	0.87442 (9)	0.69242 (9)	0.01830 (17)
C11	0.78337 (12)	0.53580 (10)	0.44672 (9)	0.01931 (18)
C12	0.84407 (13)	0.58679 (11)	0.32111 (10)	0.0241 (2)
H12	0.786842	0.676487	0.292163	0.029*
C13	0.98773 (14)	0.50692 (13)	0.23836 (11)	0.0308 (2)
H13	1.028278	0.541994	0.153099	0.037*
C14	1.07198 (14)	0.37572 (13)	0.28046 (12)	0.0321 (2)
H14	1.169324	0.320347	0.223866	0.039*
C15	1.01305 (14)	0.32603 (11)	0.40575 (11)	0.0283 (2)
H15	1.071538	0.236753	0.434436	0.034*
C16	0.87003 (13)	0.40465 (10)	0.48986 (10)	0.02336 (19)
H16	0.831446	0.369962	0.575521	0.028*
C17	0.59178 (14)	0.78967 (11)	1.11582 (10)	0.0247 (2)
H17A	0.711689	0.780661	1.078853	0.037*
H17B	0.573698	0.715273	1.183471	0.037*
H17C	0.535888	0.882592	1.151301	0.037*
C18	0.11631 (12)	0.77419 (11)	0.87182 (10)	0.02347 (19)
C19	−0.08020 (14)	0.98413 (12)	0.82766 (12)	0.0312 (2)
H19A	−0.098723	1.029690	0.906094	0.037*
H19B	−0.166938	0.933475	0.843495	0.037*
C20	−0.08800 (16)	1.09358 (14)	0.71871 (14)	0.0416 (3)
H20A	−0.064035	1.046628	0.640874	0.062*
H20B	−0.005259	1.146023	0.706811	0.062*
H20C	−0.199768	1.159291	0.737594	0.062*
N1	0.63587 (10)	0.61915 (8)	0.52807 (8)	0.01870 (16)
O1	0.56926 (8)	0.85082 (7)	0.90205 (6)	0.01874 (14)
O2	0.55020 (10)	0.45051 (8)	0.68426 (8)	0.02855 (17)
O3	0.61486 (10)	0.95404 (8)	0.64330 (7)	0.02436 (16)
O4	0.01858 (11)	0.75061 (11)	0.97188 (8)	0.0372 (2)
O5	0.08563 (9)	0.88584 (8)	0.79139 (8)	0.02685 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0213 (4)	0.0180 (4)	0.0169 (4)	−0.0062 (3)	−0.0084 (3)	0.0004 (3)
C2	0.0218 (4)	0.0193 (4)	0.0156 (4)	−0.0045 (3)	−0.0065 (3)	0.0010 (3)
C3	0.0240 (4)	0.0211 (4)	0.0172 (4)	−0.0079 (3)	−0.0070 (3)	0.0024 (3)
C4	0.0204 (4)	0.0182 (4)	0.0183 (4)	−0.0059 (3)	−0.0071 (3)	−0.0001 (3)
C5	0.0216 (4)	0.0207 (4)	0.0210 (4)	−0.0082 (3)	−0.0077 (3)	0.0001 (3)
C6	0.0212 (4)	0.0191 (4)	0.0201 (4)	−0.0062 (3)	−0.0088 (3)	−0.0009 (3)
C7	0.0228 (4)	0.0182 (4)	0.0220 (4)	−0.0068 (3)	−0.0095 (3)	−0.0008 (3)
C8	0.0277 (4)	0.0163 (4)	0.0171 (4)	−0.0030 (3)	−0.0101 (3)	0.0005 (3)
C9	0.0232 (4)	0.0170 (4)	0.0176 (4)	−0.0040 (3)	−0.0093 (3)	0.0000 (3)
C10	0.0229 (4)	0.0151 (4)	0.0170 (4)	−0.0041 (3)	−0.0075 (3)	0.0000 (3)
C11	0.0215 (4)	0.0192 (4)	0.0208 (4)	−0.0050 (3)	−0.0105 (3)	−0.0031 (3)
C12	0.0258 (5)	0.0264 (5)	0.0212 (4)	−0.0049 (4)	−0.0105 (4)	−0.0015 (3)
C13	0.0279 (5)	0.0398 (6)	0.0237 (5)	−0.0050 (4)	−0.0082 (4)	−0.0059 (4)
C14	0.0254 (5)	0.0362 (6)	0.0333 (6)	−0.0004 (4)	−0.0091 (4)	−0.0128 (5)
C15	0.0256 (5)	0.0238 (5)	0.0377 (6)	−0.0007 (4)	−0.0156 (4)	−0.0073 (4)
C16	0.0258 (5)	0.0203 (4)	0.0273 (5)	−0.0041 (3)	−0.0140 (4)	−0.0019 (3)
C17	0.0318 (5)	0.0269 (5)	0.0200 (4)	−0.0102 (4)	−0.0133 (4)	0.0021 (3)
C18	0.0220 (4)	0.0282 (5)	0.0236 (4)	−0.0104 (4)	−0.0081 (3)	−0.0012 (4)
C19	0.0214 (5)	0.0308 (5)	0.0354 (6)	−0.0035 (4)	−0.0043 (4)	−0.0008 (4)
C20	0.0310 (6)	0.0337 (6)	0.0474 (7)	−0.0021 (5)	−0.0057 (5)	0.0073 (5)
N1	0.0232 (4)	0.0154 (3)	0.0183 (3)	−0.0037 (3)	−0.0092 (3)	0.0003 (3)
O1	0.0228 (3)	0.0200 (3)	0.0160 (3)	−0.0080 (2)	−0.0081 (2)	0.0012 (2)
O2	0.0321 (4)	0.0176 (3)	0.0336 (4)	−0.0080 (3)	−0.0081 (3)	0.0041 (3)
O3	0.0334 (4)	0.0215 (3)	0.0213 (3)	−0.0130 (3)	−0.0090 (3)	0.0028 (3)
O4	0.0260 (4)	0.0512 (5)	0.0276 (4)	−0.0097 (4)	−0.0042 (3)	0.0070 (4)
O5	0.0211 (3)	0.0244 (4)	0.0303 (4)	−0.0051 (3)	−0.0040 (3)	0.0017 (3)

Geometric parameters (Å, º)

C1—C4	1.3712 (12)	C11—C12	1.3987 (14)
C1—O1	1.3775 (11)	C11—C16	1.4023 (13)
C1—C10	1.4478 (12)	C11—N1	1.4156 (12)
C2—C3	1.3712 (13)	C12—C13	1.3906 (15)
C2—O1	1.3736 (11)	C12—H12	0.9500
C2—C17	1.4849 (13)	C13—C14	1.3904 (17)
C3—C4	1.4294 (13)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.3893 (18)
C4—C5	1.5035 (13)	C14—H14	0.9500
C5—C18	1.5305 (14)	C15—C16	1.3897 (15)
C5—C6	1.5385 (14)	C15—H15	0.9500
C5—H5	1.0000	C16—H16	0.9500
C6—C7	1.5282 (14)	C17—H17A	0.9800
C6—C9	1.5420 (13)	C17—H17B	0.9800
C6—H6	1.0000	C17—H17C	0.9800
C7—O2	1.2239 (12)	C18—O4	1.2031 (13)
C7—N1	1.3737 (12)	C18—O5	1.3356 (13)
C8—N1	1.4734 (12)	C19—O5	1.4587 (13)
C8—C9	1.5316 (13)	C19—C20	1.5066 (18)
C8—H8A	0.9900	C19—H19A	0.9900
C8—H8B	0.9900	C19—H19B	0.9900
C9—C10	1.5369 (13)	C20—H20A	0.9800
C9—H9	1.0000	C20—H20B	0.9800
C10—O3	1.2289 (12)	C20—H20C	0.9800
C4—C1—O1	110.30 (8)	C12—C11—N1	118.92 (8)
C4—C1—C10	128.08 (8)	C16—C11—N1	121.42 (9)
O1—C1—C10	121.47 (8)	C13—C12—C11	120.37 (10)
C3—C2—O1	110.50 (8)	C13—C12—H12	119.8
C3—C2—C17	133.13 (9)	C11—C12—H12	119.8
O1—C2—C17	116.36 (8)	C14—C13—C12	119.97 (11)
C2—C3—C4	106.32 (8)	C14—C13—H13	120.0
C2—C3—H3	126.8	C12—C13—H13	120.0
C4—C3—H3	126.8	C15—C14—C13	119.64 (10)
C1—C4—C3	106.46 (8)	C15—C14—H14	120.2
C1—C4—C5	121.28 (8)	C13—C14—H14	120.2
C3—C4—C5	132.22 (8)	C14—C15—C16	121.15 (10)
C4—C5—C18	107.45 (8)	C14—C15—H15	119.4
C4—C5—C6	109.46 (8)	C16—C15—H15	119.4
C18—C5—C6	113.92 (8)	C15—C16—C11	119.18 (10)
C4—C5—H5	108.6	C15—C16—H16	120.4
C18—C5—H5	108.6	C11—C16—H16	120.4
C6—C5—H5	108.6	C2—C17—H17A	109.5
C7—C6—C5	111.40 (8)	C2—C17—H17B	109.5
C7—C6—C9	102.38 (7)	H17A—C17—H17B	109.5
C5—C6—C9	118.72 (8)	C2—C17—H17C	109.5
C7—C6—H6	107.9	H17A—C17—H17C	109.5
C5—C6—H6	107.9	H17B—C17—H17C	109.5
C9—C6—H6	107.9	O4—C18—O5	124.84 (10)
O2—C7—N1	126.77 (9)	O4—C18—C5	123.54 (10)
O2—C7—C6	125.30 (9)	O5—C18—C5	111.55 (8)
N1—C7—C6	107.91 (8)	O5—C19—C20	106.88 (9)
N1—C8—C9	102.56 (7)	O5—C19—H19A	110.3
N1—C8—H8A	111.3	C20—C19—H19A	110.3
C9—C8—H8A	111.3	O5—C19—H19B	110.3
N1—C8—H8B	111.3	C20—C19—H19B	110.3
C9—C8—H8B	111.3	H19A—C19—H19B	108.6
H8A—C8—H8B	109.2	C19—C20—H20A	109.5
C8—C9—C10	109.49 (8)	C19—C20—H20B	109.5
C8—C9—C6	102.03 (7)	H20A—C20—H20B	109.5
C10—C9—C6	114.13 (7)	C19—C20—H20C	109.5
C8—C9—H9	110.3	H20A—C20—H20C	109.5
C10—C9—H9	110.3	H20B—C20—H20C	109.5
C6—C9—H9	110.3	C7—N1—C11	126.27 (8)
O3—C10—C1	123.57 (9)	C7—N1—C8	111.65 (8)
O3—C10—C9	121.65 (8)	C11—N1—C8	121.13 (8)
C1—C10—C9	114.77 (8)	C2—O1—C1	106.42 (7)
C12—C11—C16	119.66 (9)	C18—O5—C19	116.94 (8)

Hydrogen-bond geometry (Å, º)

Cg1 and Cg4 are the centroids of the furan (O1/C1–C4) and phenyl (C11–C16) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1^i	0.95	2.53	3.4766 (16)	172
C17—H17A···O4^ii	0.98	2.51	3.4913 (18)	176
C17—H17B···O2^iii	0.98	2.31	3.2441 (15)	159
C17—H17C···O1^iv	0.98	2.57	3.4232 (14)	145
C19—H19B···O1^v	0.99	2.54	3.5181 (17)	168
C6—H6···Cg4^vi	1.00	2.71	3.5892 (14)	146
C14—H14···Cg1^i	0.95	2.93	3.8320 (16)	159

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