[(1R*,3S*,4S*)-3-(2-Hy­droxy­benzo­yl)-1,2,3,4-tetra­hydro-1,4-ep­oxy­naphthalen-1-yl]methyl 4-nitro­benzoate

Lough, A.J.; Ho, A.; Tam, W.

doi:10.1107/S2414314620002655

[(1R,3S,4S*)-3-(2-Hydroxybenzoyl)-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-1-yl]methyl 4-nitrobenzoate

The relative stereo- and regiochemistry of the racemic title compound, C₂₅H₁₉NO₇, were established from the crystal structure. The fused benzene ring forms dihedral angles of 77.3 (1) and 60.3 (1)° with the hydroxy-substituted benzene ring and the nitro-substituted benzene ring, respectively. The dihedral angle between the hydroxy-substituted benzene ring and the nitro-substituted benzene ring is 76.4 (1)°. An intramolecular O—H

O hydrogen bond closes an S(6) ring. In the crystal, weak C—H

O hydrogen bonds connect the molecules, forming layers parallel to (100). Within these layers, there are weak π–π stacking interactions with a ring centroid–ring centroid distance of 3.555 (1) Å.

Keywords: crystal structure; regioselectivity; weak hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314620002655/hb4338sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314620002655/hb4338Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2414314620002655/hb4338Isup3.cml Supplementary material

CCDC reference: 1986297

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.002 Å
R factor = 0.036
wR factor = 0.093
Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level A
DIFF019_ALERT_1_A  _diffrn_standards_number is missing
            Number of standards used in measurement.

Author Response: Area detector data

DIFF020_ALERT_1_A  _diffrn_standards_interval_count and
            _diffrn_standards_interval_time are missing. Number of measurements
            between standards or time (min) between standards.

Author Response: Area detector data

DIFF022_ALERT_1_A  _diffrn_standards_decay_% is missing
            Percentage decrease in standards intensity.

Author Response: Area detector data


Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.832 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report

Alert level G
PLAT398_ALERT_2_G Deviating  C-O-C    Angle From 120 for O1              96.7 Degree
PLAT432_ALERT_2_G Short Inter X...Y Contact  O7       ..C19              2.98 Ang.
                                                 1-x,-y,1-z  =      3_656 Check
PLAT793_ALERT_4_G Model has Chirality at C1          (Centro SPGR)          R Verify
PLAT793_ALERT_4_G Model has Chirality at C3          (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C4          (Centro SPGR)          S Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          2 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         17 Info

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

   3 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
   3 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

Computing details top

Data collection: APEX3 (Bruker, 2019); cell refinement: APEX3 (Bruker, 2019); data reduction: SAINT (Bruker, 2019); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: publCIF (Westrip, 2010).

[(1R*,3S*,4S*)-3-(2-Hydroxybenzoyl)-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-1-yl]methyl 4-nitrobenzoate top

Crystal data top

C₂₅H₁₉NO₇	F(000) = 928
M_r = 445.41	D_x = 1.434 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.7455 (10) Å	Cell parameters from 9213 reflections
b = 11.9504 (8) Å	θ = 2.4–27.2°
c = 11.9649 (8) Å	µ = 0.11 mm⁻¹
β = 101.898 (2)°	T = 150 K
V = 2063.1 (2) Å³	Shard, colourless
Z = 4	0.32 × 0.30 × 0.16 mm

Data collection top

Bruker Kappa APEX DUO PHOTON II diffractometer	3399 reflections with I > 2σ(I)
Radiation source: sealed tube with Bruker Triumph monochromator	R_int = 0.059
φ and ω scans	θ_max = 27.5°, θ_min = 1.4°
Absorption correction: multi-scan (Krause et al., 2015)	h = −19→19
T_min = 0.623, T_max = 0.746	k = −15→15
40054 measured reflections	l = −15→15
4727 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.039P)² + 0.5845P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4727 reflections	Δρ_max = 0.25 e Å⁻³
302 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.21520 (6)	0.45410 (8)	0.52221 (8)	0.0254 (2)
O2	0.09918 (8)	0.66077 (8)	0.55530 (9)	0.0357 (3)
O3	0.08195 (8)	0.86474 (10)	0.60434 (9)	0.0376 (3)
H3O	0.0802 (14)	0.7862 (18)	0.6067 (18)	0.069 (6)*
O4	0.37771 (6)	0.32000 (8)	0.53811 (9)	0.0295 (2)
O5	0.53204 (7)	0.32594 (9)	0.60060 (9)	0.0336 (2)
O6	0.35631 (8)	−0.23766 (9)	0.63820 (10)	0.0430 (3)
O7	0.50514 (8)	−0.25121 (9)	0.65612 (9)	0.0393 (3)
N1	0.43308 (9)	−0.19667 (10)	0.64302 (10)	0.0317 (3)
C1	0.27856 (9)	0.46052 (11)	0.44429 (11)	0.0239 (3)
C2	0.26049 (9)	0.58196 (11)	0.39894 (12)	0.0247 (3)
H2A	0.275088	0.590603	0.322264	0.030*
H2B	0.296733	0.637046	0.451839	0.030*
C3	0.15431 (9)	0.59376 (11)	0.39449 (11)	0.0238 (3)
H3A	0.120016	0.605331	0.314073	0.029*
C4	0.13143 (9)	0.47745 (11)	0.43864 (12)	0.0249 (3)
H4A	0.072919	0.474098	0.468439	0.030*
C5	0.13776 (9)	0.39344 (11)	0.34635 (12)	0.0249 (3)
C6	0.07283 (10)	0.33873 (12)	0.26533 (13)	0.0302 (3)
H6A	0.008319	0.348599	0.261361	0.036*
C7	0.10549 (11)	0.26840 (12)	0.18949 (13)	0.0332 (3)
H7A	0.062396	0.228731	0.133444	0.040*
C8	0.19923 (11)	0.25522 (12)	0.19418 (12)	0.0319 (3)
H8A	0.219548	0.206293	0.141757	0.038*
C9	0.26456 (10)	0.31274 (11)	0.27481 (12)	0.0283 (3)
H9A	0.329065	0.304773	0.277455	0.034*
C10	0.23228 (9)	0.38140 (11)	0.35039 (11)	0.0235 (3)
C11	0.13163 (9)	0.68588 (11)	0.47082 (11)	0.0254 (3)
C12	0.14368 (9)	0.80400 (11)	0.44234 (12)	0.0250 (3)
C13	0.11508 (10)	0.88844 (12)	0.50972 (12)	0.0283 (3)
C14	0.11990 (10)	1.00024 (12)	0.47954 (14)	0.0349 (4)
H14A	0.100414	1.056998	0.524970	0.042*
C15	0.15290 (11)	1.02872 (12)	0.38389 (14)	0.0369 (4)
H15A	0.155158	1.105273	0.363255	0.044*
C16	0.18300 (10)	0.94724 (12)	0.31691 (13)	0.0340 (3)
H16A	0.206590	0.967947	0.251714	0.041*
C17	0.17825 (10)	0.83600 (12)	0.34613 (12)	0.0287 (3)
H17A	0.198678	0.780174	0.300444	0.034*
C18	0.37610 (10)	0.43650 (11)	0.50427 (12)	0.0279 (3)
H18A	0.419456	0.449528	0.452497	0.034*
H18B	0.394223	0.485260	0.572100	0.034*
C19	0.46027 (9)	0.27418 (12)	0.57989 (11)	0.0253 (3)
C20	0.45169 (9)	0.15105 (11)	0.59774 (11)	0.0247 (3)
C21	0.36672 (9)	0.09770 (12)	0.56869 (12)	0.0274 (3)
H21A	0.312763	0.139404	0.536667	0.033*
C22	0.36020 (10)	−0.01641 (12)	0.58624 (12)	0.0287 (3)
H22A	0.302095	−0.053641	0.568005	0.034*
C23	0.44020 (10)	−0.07438 (12)	0.63079 (11)	0.0273 (3)
C24	0.52603 (10)	−0.02386 (12)	0.65983 (12)	0.0293 (3)
H24A	0.579934	−0.066435	0.689955	0.035*
C25	0.53146 (10)	0.09052 (12)	0.64388 (12)	0.0284 (3)
H25A	0.589463	0.127695	0.664342	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0287 (5)	0.0252 (5)	0.0235 (5)	0.0008 (4)	0.0085 (4)	0.0022 (4)
O2	0.0536 (7)	0.0288 (5)	0.0292 (5)	0.0063 (5)	0.0189 (5)	0.0028 (4)
O3	0.0493 (7)	0.0330 (6)	0.0332 (6)	0.0069 (5)	0.0145 (5)	−0.0052 (5)
O4	0.0247 (5)	0.0248 (5)	0.0380 (6)	0.0019 (4)	0.0040 (4)	0.0041 (4)
O5	0.0259 (5)	0.0370 (6)	0.0358 (6)	−0.0032 (5)	0.0019 (4)	0.0034 (5)
O6	0.0423 (7)	0.0330 (6)	0.0484 (7)	−0.0031 (5)	−0.0029 (5)	0.0024 (5)
O7	0.0485 (7)	0.0354 (6)	0.0344 (6)	0.0168 (5)	0.0097 (5)	0.0035 (5)
N1	0.0408 (8)	0.0302 (7)	0.0224 (6)	0.0058 (6)	0.0027 (5)	−0.0004 (5)
C1	0.0258 (7)	0.0230 (7)	0.0245 (7)	−0.0012 (5)	0.0085 (6)	0.0011 (5)
C2	0.0277 (7)	0.0212 (6)	0.0260 (7)	−0.0009 (5)	0.0074 (6)	0.0007 (5)
C3	0.0272 (7)	0.0219 (7)	0.0228 (7)	0.0008 (5)	0.0059 (5)	0.0002 (5)
C4	0.0236 (7)	0.0241 (7)	0.0278 (7)	0.0015 (5)	0.0072 (6)	0.0017 (6)
C5	0.0278 (7)	0.0193 (6)	0.0280 (7)	−0.0008 (5)	0.0069 (6)	0.0025 (5)
C6	0.0279 (7)	0.0254 (7)	0.0360 (8)	−0.0022 (6)	0.0036 (6)	0.0018 (6)
C7	0.0402 (9)	0.0258 (7)	0.0307 (8)	−0.0053 (6)	0.0007 (7)	−0.0019 (6)
C8	0.0441 (9)	0.0242 (7)	0.0284 (7)	0.0012 (6)	0.0098 (7)	−0.0032 (6)
C9	0.0311 (8)	0.0251 (7)	0.0305 (8)	0.0010 (6)	0.0105 (6)	0.0011 (6)
C10	0.0265 (7)	0.0202 (6)	0.0242 (7)	−0.0012 (5)	0.0058 (5)	0.0031 (5)
C11	0.0273 (7)	0.0263 (7)	0.0220 (7)	0.0039 (6)	0.0036 (6)	0.0020 (6)
C12	0.0250 (7)	0.0240 (7)	0.0239 (7)	0.0026 (5)	0.0003 (5)	0.0000 (5)
C13	0.0268 (7)	0.0280 (7)	0.0279 (7)	0.0035 (6)	0.0010 (6)	−0.0021 (6)
C14	0.0317 (8)	0.0259 (7)	0.0440 (9)	0.0040 (6)	0.0005 (7)	−0.0062 (7)
C15	0.0372 (9)	0.0223 (7)	0.0460 (9)	0.0010 (6)	−0.0032 (7)	0.0046 (7)
C16	0.0354 (8)	0.0305 (8)	0.0338 (8)	−0.0035 (6)	0.0015 (7)	0.0066 (6)
C17	0.0307 (7)	0.0267 (7)	0.0269 (7)	−0.0006 (6)	0.0018 (6)	0.0006 (6)
C18	0.0282 (7)	0.0227 (7)	0.0322 (8)	−0.0011 (6)	0.0044 (6)	0.0022 (6)
C19	0.0237 (7)	0.0326 (8)	0.0197 (7)	0.0025 (6)	0.0049 (5)	−0.0008 (6)
C20	0.0265 (7)	0.0281 (7)	0.0200 (6)	0.0027 (6)	0.0060 (5)	−0.0010 (5)
C21	0.0244 (7)	0.0293 (7)	0.0286 (7)	0.0057 (6)	0.0053 (6)	−0.0008 (6)
C22	0.0269 (7)	0.0287 (7)	0.0305 (7)	0.0004 (6)	0.0058 (6)	−0.0025 (6)
C23	0.0336 (8)	0.0277 (7)	0.0208 (7)	0.0061 (6)	0.0062 (6)	−0.0002 (5)
C24	0.0289 (8)	0.0335 (8)	0.0243 (7)	0.0090 (6)	0.0030 (6)	0.0004 (6)
C25	0.0248 (7)	0.0344 (8)	0.0251 (7)	0.0023 (6)	0.0035 (6)	−0.0018 (6)

Geometric parameters (Å, º) top

O1—C4	1.4471 (16)	C8—C9	1.396 (2)
O1—C1	1.4515 (15)	C8—H8A	0.9500
O2—C11	1.2410 (16)	C9—C10	1.3766 (19)
O3—C13	1.3523 (18)	C9—H9A	0.9500
O3—H3O	0.94 (2)	C11—C12	1.4715 (19)
O4—C19	1.3345 (16)	C12—C17	1.405 (2)
O4—C18	1.4487 (16)	C12—C13	1.4093 (19)
O5—C19	1.2066 (16)	C13—C14	1.390 (2)
O6—N1	1.2238 (16)	C14—C15	1.375 (2)
O7—N1	1.2287 (15)	C14—H14A	0.9500
N1—C23	1.4746 (19)	C15—C16	1.391 (2)
C1—C18	1.4968 (19)	C15—H15A	0.9500
C1—C10	1.5185 (18)	C16—C17	1.380 (2)
C1—C2	1.5531 (18)	C16—H16A	0.9500
C2—C3	1.5620 (19)	C17—H17A	0.9500
C2—H2A	0.9900	C18—H18A	0.9900
C2—H2B	0.9900	C18—H18B	0.9900
C3—C11	1.5112 (18)	C19—C20	1.4959 (19)
C3—C4	1.5486 (18)	C20—C21	1.3848 (19)
C3—H3A	1.0000	C20—C25	1.3942 (19)
C4—C5	1.5095 (19)	C21—C22	1.386 (2)
C4—H4A	1.0000	C21—H21A	0.9500
C5—C6	1.3788 (19)	C22—C23	1.3770 (19)
C5—C10	1.3920 (19)	C22—H22A	0.9500
C6—C7	1.393 (2)	C23—C24	1.380 (2)
C6—H6A	0.9500	C24—C25	1.385 (2)
C7—C8	1.381 (2)	C24—H24A	0.9500
C7—H7A	0.9500	C25—H25A	0.9500

C4—O1—C1	96.71 (9)	O2—C11—C12	120.38 (12)
C13—O3—H3O	104.6 (13)	O2—C11—C3	119.12 (12)
C19—O4—C18	117.40 (11)	C12—C11—C3	120.43 (12)
O6—N1—O7	124.11 (13)	C17—C12—C13	118.41 (13)
O6—N1—C23	118.42 (12)	C17—C12—C11	122.17 (12)
O7—N1—C23	117.46 (13)	C13—C12—C11	119.33 (13)
O1—C1—C18	111.35 (11)	O3—C13—C14	117.75 (13)
O1—C1—C10	101.05 (10)	O3—C13—C12	122.09 (13)
C18—C1—C10	118.44 (11)	C14—C13—C12	120.16 (14)
O1—C1—C2	100.78 (10)	C15—C14—C13	119.99 (14)
C18—C1—C2	115.17 (11)	C15—C14—H14A	120.0
C10—C1—C2	107.74 (11)	C13—C14—H14A	120.0
C1—C2—C3	101.24 (10)	C14—C15—C16	121.06 (14)
C1—C2—H2A	111.5	C14—C15—H15A	119.5
C3—C2—H2A	111.5	C16—C15—H15A	119.5
C1—C2—H2B	111.5	C17—C16—C15	119.31 (15)
C3—C2—H2B	111.5	C17—C16—H16A	120.3
H2A—C2—H2B	109.3	C15—C16—H16A	120.3
C11—C3—C4	110.90 (11)	C16—C17—C12	121.05 (14)
C11—C3—C2	112.98 (11)	C16—C17—H17A	119.5
C4—C3—C2	101.22 (10)	C12—C17—H17A	119.5
C11—C3—H3A	110.5	O4—C18—C1	106.08 (11)
C4—C3—H3A	110.5	O4—C18—H18A	110.5
C2—C3—H3A	110.5	C1—C18—H18A	110.5
O1—C4—C5	101.80 (10)	O4—C18—H18B	110.5
O1—C4—C3	101.18 (10)	C1—C18—H18B	110.5
C5—C4—C3	107.26 (11)	H18A—C18—H18B	108.7
O1—C4—H4A	115.0	O5—C19—O4	124.08 (13)
C5—C4—H4A	115.0	O5—C19—C20	124.85 (12)
C3—C4—H4A	115.0	O4—C19—C20	111.08 (11)
C6—C5—C10	121.37 (13)	C21—C20—C25	120.42 (13)
C6—C5—C4	133.71 (13)	C21—C20—C19	121.05 (12)
C10—C5—C4	104.82 (11)	C25—C20—C19	118.53 (12)
C5—C6—C7	117.43 (13)	C20—C21—C22	120.16 (13)
C5—C6—H6A	121.3	C20—C21—H21A	119.9
C7—C6—H6A	121.3	C22—C21—H21A	119.9
C8—C7—C6	121.32 (14)	C23—C22—C21	118.22 (13)
C8—C7—H7A	119.3	C23—C22—H22A	120.9
C6—C7—H7A	119.3	C21—C22—H22A	120.9
C7—C8—C9	120.95 (13)	C22—C23—C24	123.04 (14)
C7—C8—H8A	119.5	C22—C23—N1	117.66 (13)
C9—C8—H8A	119.5	C24—C23—N1	119.26 (12)
C10—C9—C8	117.70 (13)	C23—C24—C25	118.24 (13)
C10—C9—H9A	121.2	C23—C24—H24A	120.9
C8—C9—H9A	121.2	C25—C24—H24A	120.9
C9—C10—C5	121.20 (13)	C24—C25—C20	119.91 (13)
C9—C10—C1	133.92 (12)	C24—C25—H25A	120.0
C5—C10—C1	104.80 (11)	C20—C25—H25A	120.0

C4—O1—C1—C18	−178.46 (11)	O2—C11—C12—C17	−178.58 (13)
C4—O1—C1—C10	−51.79 (11)	C3—C11—C12—C17	−1.5 (2)
C4—O1—C1—C2	58.90 (11)	O2—C11—C12—C13	−2.1 (2)
O1—C1—C2—C3	−35.63 (12)	C3—C11—C12—C13	174.94 (12)
C18—C1—C2—C3	−155.56 (11)	C17—C12—C13—O3	−179.28 (12)
C10—C1—C2—C3	69.79 (12)	C11—C12—C13—O3	4.1 (2)
C1—C2—C3—C11	118.93 (12)	C17—C12—C13—C14	1.1 (2)
C1—C2—C3—C4	0.30 (12)	C11—C12—C13—C14	−175.51 (13)
C1—O1—C4—C5	51.61 (11)	O3—C13—C14—C15	−179.85 (13)
C1—O1—C4—C3	−58.89 (11)	C12—C13—C14—C15	−0.2 (2)
C11—C3—C4—O1	−84.83 (12)	C13—C14—C15—C16	−0.9 (2)
C2—C3—C4—O1	35.28 (12)	C14—C15—C16—C17	1.0 (2)
C11—C3—C4—C5	168.93 (11)	C15—C16—C17—C12	−0.1 (2)
C2—C3—C4—C5	−70.96 (12)	C13—C12—C17—C16	−0.9 (2)
O1—C4—C5—C6	151.71 (15)	C11—C12—C17—C16	175.55 (13)
C3—C4—C5—C6	−102.49 (17)	C19—O4—C18—C1	171.18 (11)
O1—C4—C5—C10	−32.04 (13)	O1—C1—C18—O4	66.60 (13)
C3—C4—C5—C10	73.76 (13)	C10—C1—C18—O4	−49.87 (15)
C10—C5—C6—C7	1.7 (2)	C2—C1—C18—O4	−179.47 (11)
C4—C5—C6—C7	177.47 (14)	C18—O4—C19—O5	6.95 (19)
C5—C6—C7—C8	−0.9 (2)	C18—O4—C19—C20	−173.23 (11)
C6—C7—C8—C9	−0.5 (2)	O5—C19—C20—C21	−178.22 (13)
C7—C8—C9—C10	1.0 (2)	O4—C19—C20—C21	1.96 (18)
C8—C9—C10—C5	−0.2 (2)	O5—C19—C20—C25	1.4 (2)
C8—C9—C10—C1	−176.44 (14)	O4—C19—C20—C25	−178.39 (11)
C6—C5—C10—C9	−1.2 (2)	C25—C20—C21—C22	0.6 (2)
C4—C5—C10—C9	−178.00 (12)	C19—C20—C21—C22	−179.80 (13)
C6—C5—C10—C1	176.00 (12)	C20—C21—C22—C23	−1.2 (2)
C4—C5—C10—C1	−0.82 (13)	C21—C22—C23—C24	0.8 (2)
O1—C1—C10—C9	−150.10 (15)	C21—C22—C23—N1	−176.67 (12)
C18—C1—C10—C9	−28.3 (2)	O6—N1—C23—C22	−16.19 (19)
C2—C1—C10—C9	104.67 (17)	O7—N1—C23—C22	162.95 (12)
O1—C1—C10—C5	33.25 (12)	O6—N1—C23—C24	166.29 (13)
C18—C1—C10—C5	155.09 (12)	O7—N1—C23—C24	−14.57 (18)
C2—C1—C10—C5	−71.98 (13)	C22—C23—C24—C25	0.4 (2)
C4—C3—C11—O2	−0.02 (17)	N1—C23—C24—C25	177.78 (12)
C2—C3—C11—O2	−112.86 (14)	C23—C24—C25—C20	−1.1 (2)
C4—C3—C11—C12	−177.14 (12)	C21—C20—C25—C24	0.6 (2)
C2—C3—C11—C12	70.02 (15)	C19—C20—C25—C24	−179.03 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2	0.94 (2)	1.67 (2)	2.5321 (15)	151.7 (19)
C3—H3A···O3ⁱ	1.00	2.48	3.4510 (17)	163
C8—H8A···O1ⁱⁱ	0.95	2.38	3.2782 (17)	157
C9—H9A···O7ⁱⁱⁱ	0.95	2.49	3.4057 (19)	161

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

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[(1R*,3S*,4S*)-3-(2-Hy­droxy­benzo­yl)-1,2,3,4-tetra­hydro-1,4-ep­oxy­naphthalen-1-yl]methyl 4-nitro­benzoate

Supporting information

Key indicators

checkCIF/PLATON results

[(1R,3S,4S*)-3-(2-Hydroxybenzoyl)-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-1-yl]methyl 4-nitrobenzoate