Ethyl 5-hydr­oxy-3-(3-methoxy­benzo­yl)-1′,5-dimethyl-2′-oxo-4,5-dihydro-1′H-spiro­[furan-2(3H),3′(2′H)-indole]-4-carboxyl­ate

The furan ring in the title compound, C₂₄H₂₅NO₇, adopts a twisted conformation. The mol­ecular structure is stabilized by an O—H...O intra­molecular hydrogen bonding inter­action which generates an S(7) ring motif. The crystal packing is stabilized by C—H...O inter­molecular inter­actions generating C(10) and C(6) chains and centrosymmetric R₂²(14) motifs.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.056
• wR factor = 0.168
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

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

---

Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Ethyl 5-hydroxy-3-(3-methoxybenzoyl)-1',5-dimethyl-2'-oxo-4,5-dihydro-1'H– spiro[furan-2(3H),3'(2'H)-indole]-4-carboxylate

Crystal data

C24H25NO7	F(000) = 928
Mr = 439.45	Dx = 1.329 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2465 reflections
a = 8.4860 (12) Å	θ = 1.8–25.0°
b = 22.446 (3) Å	µ = 0.10 mm^−1
c = 11.5348 (16) Å	T = 293 K
β = 90.305 (2)°	Block, white
V = 2197.1 (5) Å^3	0.24 × 0.23 × 0.21 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	3819 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 28.1°, θmin = 1.8°
ω scans	h = −11→10
18459 measured reflections	k = −28→28
5057 independent reflections	l = −14→15

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.168	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.1007P)^2 + 0.2499P] where P = (Fo^2 + 2Fc^2)/3
5057 reflections	(Δ/σ)max = 0.001
290 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.26 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
C1	0.5813 (2)	0.08223 (8)	0.82548 (14)	0.0472 (4)
C2	0.75734 (19)	0.07168 (7)	0.79880 (13)	0.0426 (4)
H2	0.7923	0.0353	0.8383	0.051*
C3	0.83606 (18)	0.12515 (7)	0.85575 (13)	0.0405 (3)
H3	0.8303	0.1590	0.8022	0.049*
C4	0.72649 (18)	0.13805 (7)	0.96134 (13)	0.0394 (3)
C5	0.4748 (2)	0.02885 (10)	0.82308 (18)	0.0637 (5)
H5A	0.5165	−0.0014	0.8735	0.096*
H5B	0.4682	0.0136	0.7454	0.096*
H5C	0.3716	0.0401	0.8488	0.096*
C6	0.7938 (2)	0.06648 (7)	0.67131 (14)	0.0485 (4)
C7	0.7585 (3)	0.00646 (10)	0.50360 (17)	0.0769 (6)
H7A	0.8654	0.0167	0.4819	0.092*
H7B	0.6865	0.0316	0.4600	0.092*
C8	0.7277 (4)	−0.05606 (11)	0.4775 (2)	0.0978 (9)
H8A	0.7410	−0.0629	0.3960	0.147*
H8B	0.6217	−0.0658	0.4992	0.147*
H8C	0.8002	−0.0806	0.5202	0.147*
C9	1.00727 (19)	0.11587 (7)	0.89101 (14)	0.0454 (4)
C10	1.09065 (19)	0.16715 (7)	0.94671 (14)	0.0450 (4)
C11	1.0532 (2)	0.22591 (7)	0.92170 (16)	0.0516 (4)
H11	0.9772	0.2349	0.8661	0.062*
C12	1.1311 (3)	0.27116 (8)	0.98109 (18)	0.0624 (5)
H12	1.1085	0.3107	0.9636	0.075*
C13	1.2406 (3)	0.25826 (9)	1.06496 (18)	0.0653 (5)
H13	1.2901	0.2890	1.1051	0.078*
C14	1.2780 (2)	0.19983 (9)	1.09027 (17)	0.0572 (5)
C15	1.2055 (2)	0.15391 (8)	1.02997 (15)	0.0504 (4)
H15	1.2331	0.1145	1.0448	0.061*
C16	1.4126 (3)	0.13339 (13)	1.2171 (2)	0.0852 (7)
H16A	1.4920	0.1338	1.2766	0.128*
H16B	1.4467	0.1087	1.1541	0.128*
H16C	1.3162	0.1179	1.2481	0.128*
C17	0.79509 (17)	0.12785 (7)	1.08023 (12)	0.0386 (3)
C18	0.8536 (2)	0.07700 (8)	1.13135 (14)	0.0479 (4)
H18	0.8507	0.0406	1.0930	0.057*
C19	0.9176 (3)	0.08191 (10)	1.24265 (16)	0.0622 (5)
H19	0.9576	0.0482	1.2794	0.075*
C20	0.9220 (3)	0.13582 (11)	1.29835 (16)	0.0678 (6)
H20	0.9655	0.1379	1.3724	0.081*
C21	0.8636 (2)	0.18731 (9)	1.24778 (15)	0.0571 (5)
H21	0.8680	0.2238	1.2859	0.069*
C22	0.79858 (18)	0.18201 (7)	1.13824 (13)	0.0419 (4)
C23	0.6809 (2)	0.20495 (7)	0.96644 (14)	0.0462 (4)
C24	0.7099 (3)	0.28857 (8)	1.1042 (2)	0.0706 (6)
H24A	0.7536	0.2941	1.1804	0.106*
H24B	0.5996	0.2981	1.1051	0.106*
H24C	0.7630	0.3142	1.0504	0.106*
N1	0.73026 (17)	0.22694 (6)	1.06911 (12)	0.0463 (3)
O1	0.58722 (13)	0.10306 (5)	0.94248 (10)	0.0485 (3)
O2	0.51848 (17)	0.12606 (6)	0.75074 (11)	0.0640 (4)
H2A	0.5389	0.1592	0.7765	0.096*
O3	0.8664 (2)	0.10223 (6)	0.61602 (12)	0.0764 (5)
O4	0.73686 (18)	0.01585 (6)	0.62740 (11)	0.0632 (4)
O5	1.06963 (16)	0.06788 (6)	0.87900 (14)	0.0681 (4)
O6	1.38742 (19)	0.19178 (8)	1.17660 (14)	0.0790 (5)
O7	0.61413 (18)	0.23144 (6)	0.88828 (12)	0.0676 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0499 (9)	0.0521 (9)	0.0395 (8)	−0.0004 (7)	−0.0097 (7)	−0.0054 (7)
C2	0.0518 (9)	0.0384 (8)	0.0376 (8)	0.0000 (6)	−0.0049 (7)	−0.0013 (6)
C3	0.0488 (9)	0.0355 (7)	0.0371 (7)	−0.0004 (6)	−0.0025 (6)	−0.0011 (6)
C4	0.0419 (8)	0.0374 (8)	0.0387 (7)	0.0010 (6)	−0.0053 (6)	−0.0019 (6)
C5	0.0604 (11)	0.0704 (13)	0.0603 (11)	−0.0183 (9)	−0.0030 (9)	−0.0135 (9)
C6	0.0619 (10)	0.0424 (9)	0.0412 (8)	0.0012 (8)	−0.0025 (7)	−0.0039 (7)
C7	0.1054 (18)	0.0815 (15)	0.0438 (10)	−0.0023 (13)	−0.0006 (10)	−0.0190 (10)
C8	0.148 (3)	0.0784 (17)	0.0669 (15)	0.0161 (16)	−0.0242 (15)	−0.0318 (12)
C9	0.0465 (9)	0.0426 (8)	0.0472 (8)	−0.0015 (7)	0.0037 (7)	−0.0039 (7)
C10	0.0409 (8)	0.0453 (9)	0.0489 (9)	−0.0056 (7)	0.0064 (7)	−0.0045 (7)
C11	0.0572 (10)	0.0456 (9)	0.0522 (10)	−0.0096 (8)	0.0044 (8)	0.0025 (7)
C12	0.0766 (13)	0.0429 (10)	0.0679 (12)	−0.0122 (9)	0.0081 (10)	0.0011 (8)
C13	0.0698 (13)	0.0559 (11)	0.0701 (12)	−0.0213 (10)	0.0013 (10)	−0.0132 (9)
C14	0.0493 (10)	0.0654 (12)	0.0569 (10)	−0.0126 (8)	0.0007 (8)	−0.0085 (9)
C15	0.0469 (9)	0.0474 (9)	0.0570 (10)	−0.0032 (7)	0.0020 (8)	−0.0053 (8)
C16	0.0750 (15)	0.105 (2)	0.0750 (15)	−0.0130 (13)	−0.0197 (12)	0.0116 (14)
C17	0.0401 (8)	0.0404 (8)	0.0352 (7)	−0.0023 (6)	−0.0021 (6)	−0.0010 (6)
C18	0.0531 (10)	0.0449 (9)	0.0456 (9)	0.0001 (7)	−0.0004 (7)	0.0053 (7)
C19	0.0690 (12)	0.0694 (12)	0.0481 (10)	0.0078 (10)	−0.0086 (9)	0.0171 (9)
C20	0.0721 (13)	0.0912 (16)	0.0400 (9)	0.0025 (11)	−0.0131 (9)	0.0010 (10)
C21	0.0627 (11)	0.0640 (11)	0.0446 (9)	−0.0080 (9)	−0.0034 (8)	−0.0131 (8)
C22	0.0418 (8)	0.0444 (8)	0.0395 (8)	−0.0036 (6)	0.0022 (6)	−0.0024 (6)
C23	0.0482 (9)	0.0424 (9)	0.0479 (9)	0.0072 (7)	−0.0008 (7)	0.0013 (7)
C24	0.0943 (16)	0.0409 (10)	0.0765 (14)	0.0051 (10)	0.0037 (12)	−0.0116 (9)
N1	0.0549 (8)	0.0362 (7)	0.0479 (8)	0.0018 (6)	0.0021 (6)	−0.0061 (6)
O1	0.0449 (6)	0.0565 (7)	0.0439 (6)	−0.0069 (5)	−0.0027 (5)	−0.0090 (5)
O2	0.0677 (9)	0.0679 (9)	0.0560 (8)	0.0086 (7)	−0.0215 (6)	−0.0033 (6)
O3	0.1176 (13)	0.0594 (8)	0.0524 (8)	−0.0176 (8)	0.0190 (8)	−0.0041 (6)
O4	0.0881 (10)	0.0585 (8)	0.0429 (7)	−0.0138 (7)	0.0006 (6)	−0.0142 (6)
O5	0.0543 (8)	0.0501 (7)	0.0999 (11)	0.0093 (6)	−0.0088 (7)	−0.0224 (7)
O6	0.0727 (10)	0.0843 (11)	0.0799 (10)	−0.0131 (8)	−0.0252 (8)	−0.0112 (8)
O7	0.0839 (10)	0.0573 (8)	0.0616 (8)	0.0246 (7)	−0.0166 (7)	0.0056 (6)

Geometric parameters (Å, º)

C1—O2	1.411 (2)	C11—H11	0.93
C1—O1	1.429 (2)	C12—C13	1.369 (3)
C1—C5	1.501 (3)	C12—H12	0.93
C1—C2	1.545 (2)	C13—C14	1.380 (3)
C2—C6	1.509 (2)	C13—H13	0.93
C2—C3	1.521 (2)	C14—O6	1.370 (2)
C2—H2	0.98	C14—C15	1.386 (2)
C3—C9	1.521 (2)	C15—H15	0.93
C3—C4	1.563 (2)	C16—O6	1.407 (3)
C3—H3	0.98	C16—H16A	0.96
C4—O1	1.435 (2)	C16—H16B	0.96
C4—C17	1.504 (2)	C16—H16C	0.96
C4—C23	1.552 (2)	C17—C18	1.376 (2)
C5—H5A	0.96	C17—C22	1.388 (2)
C5—H5B	0.96	C18—C19	1.396 (3)
C5—H5C	0.96	C18—H18	0.93
C6—O3	1.198 (2)	C19—C20	1.371 (3)
C6—O4	1.334 (2)	C19—H19	0.93
C7—O4	1.456 (2)	C20—C21	1.385 (3)
C7—C8	1.459 (3)	C20—H20	0.93
C7—H7A	0.97	C21—C22	1.381 (2)
C7—H7B	0.97	C21—H21	0.93
C8—H8A	0.96	C22—N1	1.409 (2)
C8—H8B	0.96	C23—O7	1.217 (2)
C8—H8C	0.96	C23—N1	1.348 (2)
C9—O5	1.208 (2)	C24—N1	1.452 (2)
C9—C10	1.494 (2)	C24—H24A	0.96
C10—C11	1.387 (2)	C24—H24B	0.96
C10—C15	1.397 (2)	C24—H24C	0.96
C11—C12	1.391 (3)	O2—H2A	0.82
O2—C1—O1	111.12 (14)	C12—C11—H11	120.5
O2—C1—C5	108.67 (15)	C13—C12—C11	120.85 (18)
O1—C1—C5	107.28 (14)	C13—C12—H12	119.6
O2—C1—C2	110.34 (14)	C11—C12—H12	119.6
O1—C1—C2	102.06 (12)	C12—C13—C14	120.32 (18)
C5—C1—C2	117.16 (15)	C12—C13—H13	119.8
C6—C2—C3	112.97 (13)	C14—C13—H13	119.8
C6—C2—C1	114.17 (14)	O6—C14—C13	115.66 (17)
C3—C2—C1	102.47 (12)	O6—C14—C15	124.34 (19)
C6—C2—H2	109.0	C13—C14—C15	120.00 (19)
C3—C2—H2	109.0	C14—C15—C10	119.55 (17)
C1—C2—H2	109.0	C14—C15—H15	120.2
C2—C3—C9	115.10 (13)	C10—C15—H15	120.2
C2—C3—C4	102.77 (12)	O6—C16—H16A	109.5
C9—C3—C4	112.85 (13)	O6—C16—H16B	109.5
C2—C3—H3	108.6	H16A—C16—H16B	109.5
C9—C3—H3	108.6	O6—C16—H16C	109.5
C4—C3—H3	108.6	H16A—C16—H16C	109.5
O1—C4—C17	111.68 (12)	H16B—C16—H16C	109.5
O1—C4—C23	109.29 (13)	C18—C17—C22	120.87 (14)
C17—C4—C23	102.00 (12)	C18—C17—C4	130.82 (14)
O1—C4—C3	105.86 (12)	C22—C17—C4	108.27 (13)
C17—C4—C3	116.95 (13)	C17—C18—C19	117.80 (16)
C23—C4—C3	110.98 (12)	C17—C18—H18	121.1
C1—C5—H5A	109.5	C19—C18—H18	121.1
C1—C5—H5B	109.5	C20—C19—C18	120.70 (17)
H5A—C5—H5B	109.5	C20—C19—H19	119.7
C1—C5—H5C	109.5	C18—C19—H19	119.7
H5A—C5—H5C	109.5	C19—C20—C21	122.04 (17)
H5B—C5—H5C	109.5	C19—C20—H20	119.0
O3—C6—O4	123.71 (16)	C21—C20—H20	119.0
O3—C6—C2	125.15 (15)	C22—C21—C20	116.98 (17)
O4—C6—C2	111.13 (14)	C22—C21—H21	121.5
O4—C7—C8	108.55 (19)	C20—C21—H21	121.5
O4—C7—H7A	110.0	C21—C22—C17	121.60 (16)
C8—C7—H7A	110.0	C21—C22—N1	128.13 (15)
O4—C7—H7B	110.0	C17—C22—N1	110.27 (13)
C8—C7—H7B	110.0	O7—C23—N1	127.82 (16)
H7A—C7—H7B	108.4	O7—C23—C4	124.03 (15)
C7—C8—H8A	109.5	N1—C23—C4	108.14 (13)
C7—C8—H8B	109.5	N1—C24—H24A	109.5
H8A—C8—H8B	109.5	N1—C24—H24B	109.5
C7—C8—H8C	109.5	H24A—C24—H24B	109.5
H8A—C8—H8C	109.5	N1—C24—H24C	109.5
H8B—C8—H8C	109.5	H24A—C24—H24C	109.5
O5—C9—C10	121.95 (16)	H24B—C24—H24C	109.5
O5—C9—C3	120.64 (15)	C23—N1—C22	111.1 (1)
C10—C9—C3	117.32 (13)	C23—N1—C24	123.9 (2)
C11—C10—C15	120.24 (16)	C22—N1—C24	125.0 (2)
C11—C10—C9	122.39 (16)	C1—O1—C4	110.33 (12)
C15—C10—C9	117.31 (15)	C1—O2—H2A	109.5
C10—C11—C12	118.99 (18)	C6—O4—C7	116.65 (15)
C10—C11—H11	120.5	C14—O6—C16	117.72 (17)
O2—C1—C2—C6	−44.97 (18)	C3—C4—C17—C18	−60.6 (2)
O1—C1—C2—C6	−163.14 (13)	O1—C4—C17—C22	−120.83 (14)
C5—C1—C2—C6	80.05 (19)	C23—C4—C17—C22	−4.22 (16)
O2—C1—C2—C3	77.53 (15)	C3—C4—C17—C22	117.02 (15)
O1—C1—C2—C3	−40.65 (15)	C22—C17—C18—C19	−0.5 (2)
C5—C1—C2—C3	−157.45 (15)	C4—C17—C18—C19	176.85 (16)
C6—C2—C3—C9	−82.00 (17)	C17—C18—C19—C20	−0.3 (3)
C1—C2—C3—C9	154.69 (13)	C18—C19—C20—C21	0.2 (3)
C6—C2—C3—C4	154.92 (13)	C19—C20—C21—C22	0.7 (3)
C1—C2—C3—C4	31.61 (15)	C20—C21—C22—C17	−1.5 (3)
C2—C3—C4—O1	−12.07 (15)	C20—C21—C22—N1	179.25 (17)
C9—C3—C4—O1	−136.64 (13)	C18—C17—C22—C21	1.4 (2)
C2—C3—C4—C17	113.06 (14)	C4—C17—C22—C21	−176.48 (15)
C9—C3—C4—C17	−11.52 (19)	C18—C17—C22—N1	−179.15 (14)
C2—C3—C4—C23	−130.54 (13)	C4—C17—C22—N1	2.93 (17)
C9—C3—C4—C23	104.89 (15)	O1—C4—C23—O7	−58.4 (2)
C3—C2—C6—O3	−5.5 (3)	C17—C4—C23—O7	−176.73 (17)
C1—C2—C6—O3	111.1 (2)	C3—C4—C23—O7	58.0 (2)
C3—C2—C6—O4	173.35 (14)	O1—C4—C23—N1	122.56 (14)
C1—C2—C6—O4	−70.08 (19)	C17—C4—C23—N1	4.23 (17)
C2—C3—C9—O5	−3.8 (2)	C3—C4—C23—N1	−121.06 (14)
C4—C3—C9—O5	113.74 (18)	O7—C23—N1—C22	178.25 (18)
C2—C3—C9—C10	179.62 (13)	C4—C23—N1—C22	−2.75 (18)
C4—C3—C9—C10	−62.85 (18)	O7—C23—N1—C24	0.2 (3)
O5—C9—C10—C11	153.38 (18)	C4—C23—N1—C24	179.20 (16)
C3—C9—C10—C11	−30.1 (2)	C21—C22—N1—C23	179.30 (17)
O5—C9—C10—C15	−29.2 (2)	C17—C22—N1—C23	−0.06 (18)
C3—C9—C10—C15	147.32 (15)	C21—C22—N1—C24	−2.7 (3)
C15—C10—C11—C12	−0.3 (3)	C17—C22—N1—C24	177.96 (17)
C9—C10—C11—C12	177.04 (16)	O2—C1—O1—C4	−83.04 (16)
C10—C11—C12—C13	−1.5 (3)	C5—C1—O1—C4	158.30 (14)
C11—C12—C13—C14	1.4 (3)	C2—C1—O1—C4	34.58 (16)
C12—C13—C14—O6	−179.19 (19)	C17—C4—O1—C1	−142.83 (13)
C12—C13—C14—C15	0.6 (3)	C23—C4—O1—C1	105.07 (14)
O6—C14—C15—C10	177.40 (17)	C3—C4—O1—C1	−14.52 (16)
C13—C14—C15—C10	−2.3 (3)	O3—C6—O4—C7	−3.6 (3)
C11—C10—C15—C14	2.2 (2)	C2—C6—O4—C7	177.56 (17)
C9—C10—C15—C14	−175.27 (15)	C8—C7—O4—C6	165.3 (2)
O1—C4—C17—C18	61.5 (2)	C13—C14—O6—C16	171.00 (19)
C23—C4—C17—C18	178.14 (16)	C15—C14—O6—C16	−8.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O7	0.82	2.17	2.959 (2)	163
C13—H13···O3^i	0.93	2.53	3.359 (3)	149
C18—H18···O5^ii	0.93	2.55	3.319 (2)	141
C21—H21···O7^i	0.93	2.60	3.230 (2)	126

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