Ethyl 10-cyano-7-hy­droxy-6-oxo-3-phenyl-8,9,10,10a-tetra­hydro-6H-benzo[c]chromene-10-carboxyl­ate

In the title compound, C₂₃H₁₉NO₅, the cyano group adopts an axial orientation and the ester group an equatorial orientation. The dihedral angle between the pendant phenyl group and the benzene ring of the fused-ring system is 25.97 (8)°. Intra­molecular O—H...O and C—H...O hydrogen bonds are observed and the packing is consolidated by C—H...O and C—H...π inter­actions.

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.3 Ratio
PLAT222_ALERT_3_C NonSolvent Resd 1  H   Uiso(max)/Uiso(min) Range        4.1 Ratio
PLAT761_ALERT_1_C CIF Contains no X-H Bonds ......................     Please Check
PLAT762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles ..........     Please Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.249 Check
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          6 Note
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         19 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.75 mm
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT793_ALERT_4_G Model has Chirality at C15         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C20         (Centro SPGR)          R Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        661 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2020) and Mercury (Macrae et al., 2020); software used to prepare material for publication: ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2020) and Mercury (Macrae et al., 2020).

Ethyl 10-cyano-7-hydroxy-6-oxo-3-phenyl-8,9,10,10a-tetrahydro-6H-benzo[c]chromene-10-carboxylate

Crystal data

C23H19NO5	F(000) = 816
Mr = 389.39	Dx = 1.359 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.7089 (8) Å	Cell parameters from 2883 reflections
b = 14.3510 (12) Å	θ = 3.0–29.1°
c = 14.2749 (15) Å	µ = 0.10 mm^−1
β = 106.946 (10)°	T = 293 K
V = 1902.6 (3) Å^3	Block, colorless
Z = 4	0.75 × 0.44 × 0.42 mm

Data collection

Xcalibur, Eos diffractometer	4413 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3119 reflections with I > 2σ(I)
Detector resolution: 15.9821 pixels mm^-1	Rint = 0.026
ω scans	θmax = 29.2°, θmin = 3.0°
Absorption correction: multi-scan (CrysalisPro; Agilent, 2014)	h = −13→13
Tmin = 0.932, Tmax = 1.000	k = −18→17
10689 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.157	H-atom parameters constrained
S = 0.95	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
4413 reflections	(Δ/σ)max = 0.010
264 parameters	Δρmax = 0.19 e Å^−3
0 restraints	Δρmin = −0.20 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.

The hydrogen atoms in title compound were placed in calculated positions, with C—H = 0.93–0.97 A° and refined using a riding model with U_iso(H) = 1.2 U_eq(C) or 1.5U_eq(C-methyl).

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

	x	y	z	Uiso*/Ueq
O1	0.53859 (10)	0.16733 (8)	0.92065 (7)	0.0410 (3)
O2	0.63028 (12)	0.27465 (8)	0.84841 (8)	0.0509 (3)
C14	0.44382 (14)	0.18379 (10)	0.74486 (11)	0.0347 (3)
O5	0.27716 (13)	−0.06937 (8)	0.61784 (10)	0.0595 (4)
C15	0.36436 (14)	0.09212 (10)	0.73953 (10)	0.0332 (3)
H15	0.431514	0.042889	0.734017	0.040*
O3	0.50815 (13)	0.31695 (9)	0.66833 (9)	0.0588 (4)
H3	0.561932	0.325224	0.723781	0.088*
C9	0.42029 (14)	0.11197 (10)	0.92053 (11)	0.0337 (3)
C10	0.32907 (15)	0.07558 (10)	0.83485 (11)	0.0347 (3)
C7	0.29134 (15)	0.04148 (11)	1.02203 (11)	0.0366 (4)
C4	0.27309 (15)	0.02080 (11)	1.11980 (11)	0.0382 (4)
C19	0.28311 (17)	0.11903 (13)	0.55664 (11)	0.0447 (4)
H19A	0.360887	0.079214	0.550748	0.054*
H19B	0.203779	0.112652	0.497179	0.054*
C16	0.11816 (17)	0.14945 (12)	0.65498 (12)	0.0450 (4)
C13	0.54193 (15)	0.21194 (11)	0.83729 (11)	0.0375 (4)
C20	0.23367 (15)	0.08697 (11)	0.64512 (11)	0.0377 (4)
C8	0.40422 (15)	0.09584 (10)	1.01183 (11)	0.0366 (4)
H8	0.469369	0.121527	1.066950	0.044*
C21	0.17320 (17)	−0.01170 (12)	0.62229 (11)	0.0437 (4)
O4	0.05006 (13)	−0.03278 (10)	0.60776 (10)	0.0649 (4)
C12	0.19570 (17)	0.00624 (12)	0.93635 (12)	0.0443 (4)
H12	0.117331	−0.029036	0.940506	0.053*
C18	0.33369 (17)	0.21905 (12)	0.56740 (12)	0.0467 (4)
H18A	0.381800	0.232559	0.518170	0.056*
H18B	0.250752	0.259856	0.555766	0.056*
C17	0.43402 (16)	0.23902 (11)	0.66616 (12)	0.0410 (4)
C11	0.21487 (17)	0.02259 (12)	0.84563 (12)	0.0443 (4)
H11	0.149569	−0.002549	0.790253	0.053*
C6	0.20395 (18)	−0.05906 (13)	1.13558 (13)	0.0507 (4)
H6	0.166517	−0.099657	1.083600	0.061*
C3	0.32765 (18)	0.08032 (12)	1.19927 (12)	0.0466 (4)
H3A	0.375026	0.134713	1.191218	0.056*
C2	0.2424 (2)	−0.02057 (16)	1.30377 (15)	0.0627 (5)
H2	0.231601	−0.034154	1.364935	0.075*
C1	0.1887 (2)	−0.08045 (15)	1.22642 (15)	0.0637 (5)
H1	0.142442	−0.135050	1.235243	0.076*
C5	0.3116 (2)	0.05875 (15)	1.29030 (14)	0.0579 (5)
H5	0.348412	0.098916	1.342756	0.070*
C22	0.2376 (2)	−0.16616 (14)	0.59282 (18)	0.0714 (6)
H22A	0.150569	−0.169084	0.538150	0.086*
H22B	0.220030	−0.197877	0.648226	0.086*
C23	0.3565 (3)	−0.21069 (18)	0.5666 (2)	0.1099 (10)
H23A	0.372605	−0.179133	0.511451	0.165*
H23B	0.333040	−0.274743	0.550071	0.165*
H23C	0.442123	−0.207456	0.621170	0.165*
N1	0.03398 (17)	0.20167 (13)	0.66178 (13)	0.0658 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0360 (5)	0.0501 (7)	0.0321 (6)	−0.0093 (5)	0.0023 (4)	0.0025 (5)
O2	0.0501 (7)	0.0508 (7)	0.0448 (7)	−0.0184 (6)	0.0029 (5)	0.0017 (5)
C14	0.0322 (7)	0.0351 (8)	0.0334 (8)	−0.0002 (6)	0.0042 (6)	0.0018 (6)
O5	0.0520 (7)	0.0435 (7)	0.0799 (10)	−0.0124 (6)	0.0143 (6)	−0.0140 (6)
C15	0.0313 (7)	0.0349 (8)	0.0296 (8)	0.0014 (6)	0.0027 (6)	0.0016 (6)
O3	0.0606 (8)	0.0537 (8)	0.0516 (8)	−0.0181 (6)	−0.0003 (6)	0.0162 (6)
C9	0.0306 (7)	0.0323 (8)	0.0347 (8)	0.0019 (6)	0.0041 (6)	0.0024 (6)
C10	0.0364 (7)	0.0323 (8)	0.0318 (8)	0.0017 (6)	0.0040 (6)	0.0029 (6)
C7	0.0385 (7)	0.0357 (8)	0.0338 (9)	0.0056 (6)	0.0078 (6)	0.0026 (6)
C4	0.0365 (7)	0.0410 (9)	0.0375 (9)	0.0092 (6)	0.0115 (6)	0.0034 (7)
C19	0.0431 (8)	0.0569 (11)	0.0311 (9)	−0.0059 (8)	0.0060 (6)	0.0023 (7)
C16	0.0375 (8)	0.0543 (10)	0.0396 (10)	0.0015 (8)	0.0056 (6)	0.0104 (8)
C13	0.0334 (7)	0.0373 (8)	0.0383 (9)	−0.0003 (6)	0.0051 (6)	0.0039 (7)
C20	0.0341 (7)	0.0448 (9)	0.0307 (8)	−0.0029 (6)	0.0039 (6)	0.0012 (7)
C8	0.0379 (7)	0.0349 (8)	0.0324 (8)	0.0026 (6)	0.0028 (6)	−0.0005 (6)
C21	0.0431 (9)	0.0534 (10)	0.0307 (9)	−0.0102 (8)	0.0049 (6)	−0.0038 (7)
O4	0.0483 (7)	0.0789 (10)	0.0652 (9)	−0.0248 (7)	0.0132 (6)	−0.0154 (7)
C12	0.0437 (8)	0.0481 (10)	0.0389 (9)	−0.0103 (7)	0.0086 (7)	0.0044 (7)
C18	0.0430 (9)	0.0564 (11)	0.0361 (9)	−0.0032 (7)	0.0045 (7)	0.0121 (8)
C17	0.0377 (8)	0.0423 (9)	0.0399 (9)	−0.0027 (7)	0.0064 (6)	0.0052 (7)
C11	0.0444 (8)	0.0481 (10)	0.0344 (9)	−0.0110 (7)	0.0022 (7)	0.0010 (7)
C6	0.0548 (10)	0.0529 (11)	0.0485 (11)	−0.0025 (8)	0.0214 (8)	0.0004 (8)
C3	0.0476 (9)	0.0504 (10)	0.0426 (10)	0.0034 (8)	0.0144 (7)	−0.0021 (8)
C2	0.0683 (12)	0.0819 (15)	0.0468 (12)	0.0071 (11)	0.0307 (10)	0.0081 (10)
C1	0.0711 (12)	0.0699 (14)	0.0602 (13)	−0.0059 (11)	0.0348 (10)	0.0087 (10)
C5	0.0591 (11)	0.0746 (13)	0.0424 (11)	0.0072 (10)	0.0185 (8)	−0.0082 (9)
C22	0.0747 (13)	0.0481 (12)	0.0924 (17)	−0.0228 (10)	0.0258 (11)	−0.0196 (11)
C23	0.100 (2)	0.0564 (15)	0.188 (3)	−0.0203 (13)	0.065 (2)	−0.0405 (17)
N1	0.0558 (9)	0.0742 (11)	0.0700 (12)	0.0198 (9)	0.0222 (8)	0.0222 (9)

Geometric parameters (Å, º)

O1—C13	1.3599 (18)	C7—C4	1.487 (2)
O1—C9	1.3961 (17)	C4—C6	1.379 (2)
O2—C13	1.2212 (18)	C4—C3	1.395 (2)
C14—C17	1.355 (2)	C19—C18	1.510 (2)
C14—C13	1.442 (2)	C19—C20	1.546 (2)
C14—C15	1.516 (2)	C16—N1	1.134 (2)
O5—C21	1.321 (2)	C16—C20	1.474 (2)
O5—C22	1.457 (2)	C20—C21	1.531 (2)
C15—C10	1.516 (2)	C21—O4	1.1913 (18)
C15—C20	1.5604 (19)	C12—C11	1.381 (2)
O3—C17	1.3255 (19)	C18—C17	1.489 (2)
C9—C8	1.377 (2)	C6—C1	1.382 (2)
C9—C10	1.386 (2)	C3—C5	1.388 (2)
C10—C11	1.390 (2)	C2—C5	1.363 (3)
C7—C8	1.387 (2)	C2—C1	1.376 (3)
C7—C12	1.397 (2)	C22—C23	1.460 (3)
C13—O1—C9	119.76 (11)	O1—C13—C14	119.40 (13)
C17—C14—C13	117.57 (14)	C16—C20—C21	109.13 (13)
C17—C14—C15	123.65 (13)	C16—C20—C19	108.83 (12)
C13—C14—C15	118.68 (13)	C21—C20—C19	107.00 (13)
C21—O5—C22	117.30 (14)	C16—C20—C15	109.78 (13)
C14—C15—C10	109.62 (12)	C21—C20—C15	113.11 (12)
C14—C15—C20	111.00 (12)	C19—C20—C15	108.88 (12)
C10—C15—C20	115.36 (12)	C9—C8—C7	120.33 (13)
C8—C9—C10	123.53 (14)	O4—C21—O5	125.08 (16)
C8—C9—O1	114.50 (12)	O4—C21—C20	125.09 (16)
C10—C9—O1	121.96 (13)	O5—C21—C20	109.79 (13)
C9—C10—C11	115.70 (14)	C11—C12—C7	121.50 (15)
C9—C10—C15	118.66 (13)	C17—C18—C19	112.50 (13)
C11—C10—C15	125.57 (13)	O3—C17—C14	124.59 (14)
C8—C7—C12	117.11 (14)	O3—C17—C18	112.66 (13)
C8—C7—C4	121.65 (13)	C14—C17—C18	122.73 (14)
C12—C7—C4	121.25 (14)	C12—C11—C10	121.79 (14)
C6—C4—C3	117.61 (15)	C4—C6—C1	121.87 (18)
C6—C4—C7	121.05 (15)	C5—C3—C4	120.32 (17)
C3—C4—C7	121.33 (15)	C5—C2—C1	119.68 (18)
C18—C19—C20	111.65 (14)	C2—C1—C6	119.68 (19)
N1—C16—C20	176.08 (18)	C2—C5—C3	120.84 (18)
O2—C13—O1	115.36 (13)	O5—C22—C23	107.97 (17)
O2—C13—C14	125.24 (14)

Hydrogen-bond geometry (Å, º)

Cg2 and Cg3 are the centroids of the C1–C6 and C7–C12 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.86	2.5702 (16)	145
C11—H11···O4	0.93	2.54	3.399 (2)	154
C18—H18B···O1^i	0.97	2.60	3.4289 (19)	144
C19—H19B···O2^i	0.97	2.60	3.285 (2)	128
C15—H15···Cg2^ii	0.98	2.95	3.7685 (17)	142
C23—H23B···Cg3^iii	0.96	2.82	3.686 (3)	151

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1, −y, −z+2; (iii) −x+1/2, y−1/2, −z+3/2.