Crystal structure, Hirshfeld surface and frontier mol­ecular orbital analysis of 9-(3-bromo-4-hy­droxy-5-meth­oxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione

Suresh Babu, N.; Sughanya, V.; Praveenkumar, D.; Sundararajan, M.L.

doi:10.1107/S2056989021010690

Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

N. Suresh Babu, V. Sughanya, D. Praveenkumar and M. L. Sundararajan

In the xanthene moiety of the title compound, the central ring adopts a flattened-boat conformation whereas the cyclohexenone rings adopt envelope conformations. In the crystal, molecules are linked by pairs of O—H

O hydrogen bonds, forming inversion dimers with an $R_{2}^{2}$ (20) ring motif.

Keywords: crystal structure; dimedone; xanthene; xanthenedione; pyran ring.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989021010690/zn2010sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989021010690/zn2010Isup3.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989021010690/zn2010Isup3.cml Supplementary material

CCDC reference: 2064558

checkCIF report

Key indicators

Structure: I

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.027
wR factor = 0.072
Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1      ..O1       .       3.14 Ang.
                                                1-x,1-y,1-z  =      2_666 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16A     ..BR1      .       2.94 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min).          8 Note

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          1 Report
PLAT164_ALERT_4_G Nr. of Refined C-H H-Atoms in Heavy-Atom Struct.          1 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        78% Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          4 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          8 Info

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

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

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: APEX3 and SAINT-Plus (Bruker, 2016); data reduction: SAINT-Plus and XPREP (Bruker, 2016); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015a) and publCIF (Westrip, 2010).

9-(3-Bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione top

Crystal data top

C₂₄H₂₇BrO₅	F(000) = 492
M_r = 475.36	D_x = 1.372 Mg m⁻³
Triclinic, P1	Melting point: 495 K
a = 9.851 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.763 (3) Å	Cell parameters from 9325 reflections
c = 12.313 (3) Å	θ = 2.6–30.0°
α = 82.38 (1)°	µ = 1.82 mm⁻¹
β = 66.900 (9)°	T = 296 K
γ = 73.484 (10)°	BLOCK, yellow
V = 1150.9 (5) Å³	0.30 × 0.25 × 0.20 mm
Z = 2

Data collection top

Bruker Kappa APEX3 CMOS diffractometer	4052 independent reflections
Radiation source: fine-focus sealed tube	3694 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and φ scan	θ_max = 25.0°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −11→11
T_min = 0.550, T_max = 0.746	k = −12→12
47600 measured reflections	l = −14→14

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.072	w = 1/[σ²(F_o²) + (0.0296P)² + 0.6561P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
4052 reflections	Δρ_max = 0.32 e Å⁻³
276 parameters	Δρ_min = −0.50 e Å⁻³

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
Br1	0.49132 (3)	0.69406 (2)	0.62363 (2)	0.05292 (10)
C1	0.5946 (2)	0.11911 (17)	0.64639 (15)	0.0319 (4)
C2	0.4569 (2)	0.0735 (2)	0.66746 (17)	0.0412 (5)
H2A	0.484623	−0.020439	0.666673	0.049*
H2B	0.420396	0.105743	0.603872	0.049*
C3	0.3280 (2)	0.1192 (2)	0.78588 (18)	0.0423 (5)
C4	0.2057 (3)	0.0452 (3)	0.8150 (2)	0.0676 (7)
H4A	0.250419	−0.046032	0.819885	0.101*
H4B	0.125530	0.073181	0.889224	0.101*
H4C	0.164507	0.062167	0.754031	0.101*
C5	0.2564 (3)	0.2644 (2)	0.7781 (3)	0.0617 (7)
H5A	0.332860	0.310996	0.759881	0.092*
H5B	0.215134	0.281231	0.717207	0.092*
H5C	0.176157	0.292245	0.852400	0.092*
C6	0.3982 (3)	0.0887 (2)	0.88067 (18)	0.0516 (6)
H6A	0.320679	0.124356	0.954643	0.062*
H6B	0.427417	−0.004661	0.891856	0.062*
C7	0.5345 (2)	0.13965 (17)	0.85383 (16)	0.0366 (4)
C8	0.6339 (2)	0.15206 (16)	0.72946 (15)	0.0313 (4)
C9	0.7704 (2)	0.20575 (17)	0.70112 (16)	0.0322 (4)
C10	0.8672 (2)	0.19047 (17)	0.57072 (16)	0.0322 (4)
C11	1.0196 (2)	0.2146 (2)	0.52605 (19)	0.0439 (5)
C12	1.1113 (2)	0.2068 (2)	0.3948 (2)	0.0495 (5)
H12A	1.180310	0.121046	0.378089	0.059*
H12B	1.172975	0.268803	0.372815	0.059*
C13	1.0158 (2)	0.2333 (2)	0.31752 (18)	0.0428 (5)
C14	0.9298 (3)	0.3771 (2)	0.3217 (2)	0.0617 (7)
H14A	1.001793	0.429336	0.291989	0.093*
H14B	0.869236	0.392418	0.273983	0.093*
H14C	0.864478	0.399531	0.401812	0.093*
C15	1.1185 (3)	0.1973 (3)	0.1891 (2)	0.0627 (7)
H15A	1.189481	0.250422	0.158058	0.094*
H15B	1.173617	0.107698	0.186491	0.094*
H15C	1.056780	0.211083	0.142489	0.094*
C16	0.9043 (2)	0.14713 (19)	0.36435 (16)	0.0378 (4)
H16A	0.831875	0.172240	0.325133	0.045*
H16B	0.960435	0.057845	0.345098	0.045*
C17	0.8192 (2)	0.15590 (17)	0.49441 (15)	0.0313 (4)
C18	0.7174 (2)	0.34791 (17)	0.73598 (16)	0.0318 (4)
C19	0.7345 (2)	0.38397 (18)	0.83369 (16)	0.0342 (4)
H19	0.786711	0.322584	0.873846	0.041*
C20	0.6744 (2)	0.51052 (18)	0.87108 (16)	0.0346 (4)
C21	0.7625 (3)	0.4676 (3)	1.0299 (2)	0.0604 (7)
H21A	0.759056	0.510392	1.094887	0.091*
H21B	0.716974	0.395977	1.059224	0.091*
H21C	0.866680	0.436440	0.977932	0.091*
C22	0.5972 (2)	0.60496 (17)	0.81104 (16)	0.0341 (4)
C23	0.5878 (2)	0.56797 (18)	0.71128 (16)	0.0334 (4)
C24	0.6451 (2)	0.44079 (18)	0.67421 (16)	0.0345 (4)
H24	0.634765	0.418239	0.608017	0.041*
O1	0.68252 (15)	0.12340 (13)	0.52771 (10)	0.0355 (3)
O2	0.56680 (19)	0.16747 (15)	0.93260 (12)	0.0493 (4)
O3	1.0717 (2)	0.2361 (2)	0.59419 (16)	0.0743 (6)
O4	0.53332 (19)	0.72988 (13)	0.84657 (13)	0.0476 (4)
H4	0.531593	0.735147	0.912952	0.071*
O5	0.68156 (19)	0.55546 (14)	0.96789 (13)	0.0489 (4)
H9	0.829 (2)	0.156 (2)	0.7488 (18)	0.035 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.06708 (17)	0.03847 (13)	0.05825 (15)	0.00106 (10)	−0.03853 (12)	−0.00177 (9)
C1	0.0423 (10)	0.0251 (9)	0.0255 (9)	−0.0070 (8)	−0.0102 (8)	−0.0021 (7)
C2	0.0519 (12)	0.0401 (11)	0.0348 (10)	−0.0190 (9)	−0.0126 (9)	−0.0071 (8)
C3	0.0471 (12)	0.0427 (11)	0.0369 (10)	−0.0158 (9)	−0.0104 (9)	−0.0078 (9)
C4	0.0628 (16)	0.0841 (19)	0.0579 (15)	−0.0401 (15)	−0.0067 (13)	−0.0113 (14)
C5	0.0558 (14)	0.0518 (14)	0.0809 (18)	−0.0008 (11)	−0.0323 (13)	−0.0200 (13)
C6	0.0582 (14)	0.0608 (14)	0.0293 (10)	−0.0206 (11)	−0.0070 (10)	0.0027 (10)
C7	0.0520 (12)	0.0273 (9)	0.0273 (9)	−0.0037 (8)	−0.0157 (9)	−0.0007 (7)
C8	0.0428 (10)	0.0230 (8)	0.0262 (9)	−0.0039 (7)	−0.0138 (8)	−0.0010 (7)
C9	0.0409 (10)	0.0287 (9)	0.0294 (9)	−0.0032 (8)	−0.0191 (8)	−0.0027 (7)
C10	0.0371 (10)	0.0267 (9)	0.0319 (9)	−0.0021 (7)	−0.0153 (8)	−0.0036 (7)
C11	0.0407 (11)	0.0464 (12)	0.0470 (12)	−0.0073 (9)	−0.0206 (10)	−0.0034 (9)
C12	0.0385 (11)	0.0577 (14)	0.0491 (12)	−0.0127 (10)	−0.0115 (10)	−0.0049 (10)
C13	0.0417 (11)	0.0446 (11)	0.0349 (10)	−0.0099 (9)	−0.0080 (9)	0.0006 (9)
C14	0.0723 (17)	0.0451 (13)	0.0584 (15)	−0.0140 (12)	−0.0192 (13)	0.0114 (11)
C15	0.0563 (14)	0.0825 (18)	0.0388 (12)	−0.0235 (13)	−0.0026 (11)	−0.0026 (12)
C16	0.0416 (11)	0.0396 (10)	0.0286 (9)	−0.0056 (8)	−0.0115 (8)	−0.0050 (8)
C17	0.0345 (10)	0.0265 (9)	0.0300 (9)	−0.0038 (7)	−0.0116 (8)	−0.0017 (7)
C18	0.0361 (10)	0.0308 (9)	0.0305 (9)	−0.0077 (8)	−0.0138 (8)	−0.0049 (7)
C19	0.0412 (10)	0.0338 (10)	0.0328 (9)	−0.0091 (8)	−0.0194 (8)	−0.0009 (8)
C20	0.0432 (11)	0.0373 (10)	0.0287 (9)	−0.0155 (8)	−0.0140 (8)	−0.0050 (8)
C21	0.0862 (18)	0.0673 (16)	0.0484 (13)	−0.0213 (14)	−0.0426 (13)	−0.0100 (11)
C22	0.0376 (10)	0.0295 (9)	0.0347 (10)	−0.0097 (8)	−0.0104 (8)	−0.0060 (8)
C23	0.0361 (10)	0.0318 (9)	0.0346 (10)	−0.0061 (8)	−0.0175 (8)	−0.0001 (8)
C24	0.0415 (10)	0.0345 (10)	0.0317 (9)	−0.0076 (8)	−0.0178 (8)	−0.0062 (8)
O1	0.0420 (7)	0.0434 (7)	0.0240 (6)	−0.0152 (6)	−0.0112 (5)	−0.0044 (5)
O2	0.0715 (10)	0.0505 (9)	0.0272 (7)	−0.0142 (8)	−0.0204 (7)	−0.0024 (6)
O3	0.0588 (11)	0.1243 (17)	0.0587 (11)	−0.0374 (11)	−0.0297 (9)	−0.0097 (11)
O4	0.0675 (10)	0.0325 (7)	0.0435 (8)	−0.0032 (7)	−0.0248 (8)	−0.0116 (6)
O5	0.0739 (10)	0.0411 (8)	0.0421 (8)	−0.0138 (7)	−0.0303 (8)	−0.0103 (6)

Geometric parameters (Å, º) top

Br1—C23	1.8954 (19)	C12—H12A	0.9700
C1—C8	1.344 (3)	C12—H12B	0.9700
C1—O1	1.378 (2)	C13—C16	1.530 (3)
C1—C2	1.489 (3)	C13—C14	1.535 (3)
C2—C3	1.537 (3)	C13—C15	1.536 (3)
C2—H2A	0.9700	C14—H14A	0.9600
C2—H2B	0.9700	C14—H14B	0.9600
C3—C5	1.529 (3)	C14—H14C	0.9600
C3—C4	1.530 (3)	C15—H15A	0.9600
C3—C6	1.534 (3)	C15—H15B	0.9600
C4—H4A	0.9600	C15—H15C	0.9600
C4—H4B	0.9600	C16—C17	1.489 (3)
C4—H4C	0.9600	C16—H16A	0.9700
C5—H5A	0.9600	C16—H16B	0.9700
C5—H5B	0.9600	C17—O1	1.378 (2)
C5—H5C	0.9600	C18—C24	1.380 (3)
C6—C7	1.494 (3)	C18—C19	1.395 (2)
C6—H6A	0.9700	C19—C20	1.383 (3)
C6—H6B	0.9700	C19—H19	0.9300
C7—O2	1.227 (2)	C20—O5	1.378 (2)
C7—C8	1.471 (3)	C20—C22	1.400 (3)
C8—C9	1.511 (3)	C21—O5	1.403 (3)
C9—C10	1.515 (3)	C21—H21A	0.9600
C9—C18	1.530 (2)	C21—H21B	0.9600
C9—H9	0.98 (2)	C21—H21C	0.9600
C10—C17	1.336 (3)	C22—O4	1.362 (2)
C10—C11	1.470 (3)	C22—C23	1.384 (3)
C11—O3	1.216 (3)	C23—C24	1.387 (3)
C11—C12	1.510 (3)	C24—H24	0.9300
C12—C13	1.533 (3)	O4—H4	0.8200

C8—C1—O1	122.25 (17)	H12A—C12—H12B	107.6
C8—C1—C2	126.24 (17)	C16—C13—C12	107.75 (17)
O1—C1—C2	111.51 (15)	C16—C13—C14	110.89 (18)
C1—C2—C3	112.21 (16)	C12—C13—C14	110.14 (19)
C1—C2—H2A	109.2	C16—C13—C15	108.20 (18)
C3—C2—H2A	109.2	C12—C13—C15	110.44 (19)
C1—C2—H2B	109.2	C14—C13—C15	109.39 (19)
C3—C2—H2B	109.2	C13—C14—H14A	109.5
H2A—C2—H2B	107.9	C13—C14—H14B	109.5
C5—C3—C4	109.3 (2)	H14A—C14—H14B	109.5
C5—C3—C6	111.04 (18)	C13—C14—H14C	109.5
C4—C3—C6	109.72 (19)	H14A—C14—H14C	109.5
C5—C3—C2	109.94 (19)	H14B—C14—H14C	109.5
C4—C3—C2	109.43 (17)	C13—C15—H15A	109.5
C6—C3—C2	107.36 (18)	C13—C15—H15B	109.5
C3—C4—H4A	109.5	H15A—C15—H15B	109.5
C3—C4—H4B	109.5	C13—C15—H15C	109.5
H4A—C4—H4B	109.5	H15A—C15—H15C	109.5
C3—C4—H4C	109.5	H15B—C15—H15C	109.5
H4A—C4—H4C	109.5	C17—C16—C13	112.68 (16)
H4B—C4—H4C	109.5	C17—C16—H16A	109.1
C3—C5—H5A	109.5	C13—C16—H16A	109.1
C3—C5—H5B	109.5	C17—C16—H16B	109.1
H5A—C5—H5B	109.5	C13—C16—H16B	109.1
C3—C5—H5C	109.5	H16A—C16—H16B	107.8
H5A—C5—H5C	109.5	C10—C17—O1	123.42 (16)
H5B—C5—H5C	109.5	C10—C17—C16	125.17 (18)
C7—C6—C3	115.04 (17)	O1—C17—C16	111.41 (15)
C7—C6—H6A	108.5	C24—C18—C19	119.37 (17)
C3—C6—H6A	108.5	C24—C18—C9	119.97 (16)
C7—C6—H6B	108.5	C19—C18—C9	120.58 (16)
C3—C6—H6B	108.5	C20—C19—C18	120.33 (17)
H6A—C6—H6B	107.5	C20—C19—H19	119.8
O2—C7—C8	119.91 (19)	C18—C19—H19	119.8
O2—C7—C6	121.64 (18)	O5—C20—C19	124.98 (18)
C8—C7—C6	118.42 (17)	O5—C20—C22	114.18 (16)
C1—C8—C7	117.75 (18)	C19—C20—C22	120.84 (17)
C1—C8—C9	123.31 (16)	O5—C21—H21A	109.5
C7—C8—C9	118.90 (16)	O5—C21—H21B	109.5
C8—C9—C10	109.09 (15)	H21A—C21—H21B	109.5
C8—C9—C18	110.02 (15)	O5—C21—H21C	109.5
C10—C9—C18	111.38 (15)	H21A—C21—H21C	109.5
C8—C9—H9	107.8 (12)	H21B—C21—H21C	109.5
C10—C9—H9	110.4 (11)	O4—C22—C23	119.68 (17)
C18—C9—H9	108.0 (12)	O4—C22—C20	122.66 (17)
C17—C10—C11	118.59 (17)	C23—C22—C20	117.67 (16)
C17—C10—C9	122.45 (17)	C22—C23—C24	121.99 (17)
C11—C10—C9	118.96 (16)	C22—C23—Br1	119.16 (14)
O3—C11—C10	120.3 (2)	C24—C23—Br1	118.84 (14)
O3—C11—C12	121.2 (2)	C18—C24—C23	119.71 (16)
C10—C11—C12	118.47 (18)	C18—C24—H24	120.1
C11—C12—C13	114.73 (18)	C23—C24—H24	120.1
C11—C12—H12A	108.6	C1—O1—C17	118.39 (14)
C13—C12—H12A	108.6	C22—O4—H4	109.5
C11—C12—H12B	108.6	C20—O5—C21	117.51 (16)
C13—C12—H12B	108.6

C8—C1—C2—C3	24.0 (3)	C12—C13—C16—C17	49.6 (2)
O1—C1—C2—C3	−156.46 (16)	C14—C13—C16—C17	−71.0 (2)
C1—C2—C3—C5	72.5 (2)	C15—C13—C16—C17	169.04 (18)
C1—C2—C3—C4	−167.4 (2)	C11—C10—C17—O1	175.94 (16)
C1—C2—C3—C6	−48.4 (2)	C9—C10—C17—O1	−4.1 (3)
C5—C3—C6—C7	−67.4 (2)	C11—C10—C17—C16	−4.0 (3)
C4—C3—C6—C7	171.63 (19)	C9—C10—C17—C16	175.98 (17)
C2—C3—C6—C7	52.8 (2)	C13—C16—C17—C10	−24.5 (3)
C3—C6—C7—O2	151.79 (19)	C13—C16—C17—O1	155.55 (16)
C3—C6—C7—C8	−30.3 (3)	C8—C9—C18—C24	−68.8 (2)
O1—C1—C8—C7	−177.95 (16)	C10—C9—C18—C24	52.3 (2)
C2—C1—C8—C7	1.5 (3)	C8—C9—C18—C19	107.97 (19)
O1—C1—C8—C9	4.6 (3)	C10—C9—C18—C19	−130.94 (18)
C2—C1—C8—C9	−175.96 (17)	C24—C18—C19—C20	2.5 (3)
O2—C7—C8—C1	179.28 (17)	C9—C18—C19—C20	−174.21 (17)
C6—C7—C8—C1	1.3 (3)	C18—C19—C20—O5	178.32 (18)
O2—C7—C8—C9	−3.1 (3)	C18—C19—C20—C22	−0.9 (3)
C6—C7—C8—C9	178.92 (17)	O5—C20—C22—O4	−0.8 (3)
C1—C8—C9—C10	−10.9 (2)	C19—C20—C22—O4	178.46 (18)
C7—C8—C9—C10	171.59 (15)	O5—C20—C22—C23	178.72 (17)
C1—C8—C9—C18	111.52 (19)	C19—C20—C22—C23	−2.0 (3)
C7—C8—C9—C18	−65.9 (2)	O4—C22—C23—C24	−177.13 (18)
C8—C9—C10—C17	10.7 (2)	C20—C22—C23—C24	3.3 (3)
C18—C9—C10—C17	−111.0 (2)	O4—C22—C23—Br1	2.0 (3)
C8—C9—C10—C11	−169.39 (16)	C20—C22—C23—Br1	−177.59 (14)
C18—C9—C10—C11	69.0 (2)	C19—C18—C24—C23	−1.3 (3)
C17—C10—C11—O3	−174.2 (2)	C9—C18—C24—C23	175.50 (17)
C9—C10—C11—O3	5.9 (3)	C22—C23—C24—C18	−1.7 (3)
C17—C10—C11—C12	3.5 (3)	Br1—C23—C24—C18	179.19 (14)
C9—C10—C11—C12	−176.41 (18)	C8—C1—O1—C17	3.6 (2)
O3—C11—C12—C13	−156.7 (2)	C2—C1—O1—C17	−175.94 (15)
C10—C11—C12—C13	25.6 (3)	C10—C17—O1—C1	−3.8 (3)
C11—C12—C13—C16	−50.9 (2)	C16—C17—O1—C1	176.09 (15)
C11—C12—C13—C14	70.2 (2)	C19—C20—O5—C21	3.2 (3)
C11—C12—C13—C15	−168.9 (2)	C22—C20—O5—C21	−177.50 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6B···O2ⁱ	0.97	2.60	3.377 (3)	137
C16—H16A···Br1ⁱⁱ	0.97	2.94	3.736 (2)	140
O4—H4···O2ⁱⁱⁱ	0.82	2.04	2.768 (2)	148
O4—H4···O5	0.82	2.28	2.701 (2)	113

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

The global reactivity descriptors (eV) of the title compound top

Frontier molecular orbitals	Energy
E_HOMO	-5.8915
E_LUMO	-1.9353
E_HOMO-1	-6.2499
E_LUMO+1	-1.0419
(E_HOMO - E_LUMO) gap	3.9562
(E_HOMO-1 - E_LUMO+1) gap	5.2080
Chemical potential (µ)	3.9134
Chemical hardness (η)	1.9781
Chemical softness (S)	0.5055
Electrophilicity index (ω)	3.8711

The frontier molecular orbital energies of the title compound top

Orbitals	a.u	eV
V₁₃₀	-0.00040	-0.01088
V₁₂₉	-0.00433	-0.11782
V₁₂₈	-0.00548	-0.14911
V₁₂₇	-0.00823	-0.22394
V₁₂₆	-0.01615	-0.43945
V₁₂₅	-0.03829	-1.04190
V₁₂₄	-0.07112	1.93524
O₁₂₃	-0.21651	-5.89145
O₁₂₂	-0.22968	-6.24982
O₁₂₁	-0.24696	-6.72002
O₁₂₀	-0.25386	-6.90778
O₁₁₉	-0.25681	-6.98805
O₁₁₈	-0.28020	-7.62452
O₁₁₇	-0.28631	-7.79078
O₁₁₆	-0.29688	-8.07840
O₁₁₅	-0.33387	-9.08493
O₁₁₄	-0.33908	-9.22670

* O- Occupied orbital V- Vacant orbital a.u-atomic unit eV-Electron Volt

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Crystal structure, Hirshfeld surface and frontier mol­ecular orbital analysis of 9-(3-bromo-4-hy­droxy-5-meth­oxy­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6,7,9-hexa­hydro-1H-xanthene-1,8(2H)-dione

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Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione