(4-Hydroxy­phen­yl)(2,4,6-trihydroxy­phen­yl)methanone monohydrate

Choudhary, M.I.; Naheed, S.; Anjum, S.; Nasim, S.; Atta-ur-Rahman; Fun, H.-K.

doi:10.1107/S160053680503165X

(4-Hydroxyphenyl)(2,4,6-trihydroxyphenyl)methanone monohydrate

M. I. Choudhary, S. Naheed, S. Anjum, S. Nasim, Atta-ur-Rahman and H.-K. Fun

The title compound, C₁₃H₁₀O₅, is a benzophenone derivative containing phloroglucinol and p-hydroxybenzoyl groups. The p-hydroxybenzoyl group is twisted out of the plane of the phloroglucinol group as a result of steric hindrance [dihedral angle = 50.2 (1)°]. In the crystal packing, screw-related molecules are linked by O—H

O hydrogen bonds to form a zigzag layer parallel to (10 $\overline{1}$ ). Adjacent layers are interlinked by O—H

O hydrogen bonds involving the solvent water molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680503165X/ci6666sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680503165X/ci6666Isup2.hkl Contains datablock I

CCDC reference: 290005

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
R factor = 0.067
wR factor = 0.125
Data-to-parameter ratio = 11.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

(4-Hydroxyphenyl)(2,4,6-trihydroxyphenyl)methanone monohydrate top

Crystal data top

C₁₃H₁₀O₅·H₂O	F(000) = 552
M_r = 264.23	D_x = 1.445 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 545–547 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.305 (2) Å	Cell parameters from 1444 reflections
b = 10.365 (2) Å	θ = 1.5–25.0°
c = 8.8087 (17) Å	µ = 0.12 mm⁻¹
β = 90.949 (4)°	T = 293 K
V = 1214.6 (4) Å³	Needle, yellow
Z = 4	0.39 × 0.07 × 0.05 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	2134 independent reflections
Radiation source: fine-focus sealed tube	1100 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.080
Detector resolution: 8.33 pixels mm^-1	θ_max = 25.0°, θ_min = 1.5°
ω scans	h = −13→15
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
T_min = 0.957, T_max = 0.994	l = −10→10
5991 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0342P)²] where P = (F_o² + 2F_c²)/3
2134 reflections	(Δ/σ)_max = 0.001
180 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
O1W	0.7608 (3)	0.2964 (4)	0.0738 (6)	0.0905 (14)
O1	0.37354 (19)	0.5928 (2)	−0.2448 (3)	0.0618 (9)
H1A	0.3366	0.6295	−0.1850	0.093*
O2	0.82927 (19)	0.5273 (2)	−0.0385 (3)	0.0489 (8)
O3	0.94937 (18)	0.6526 (2)	0.1313 (3)	0.0541 (9)
H3A	0.9230	0.5901	0.0897	0.081*
O4	0.91133 (17)	1.1095 (2)	0.1443 (3)	0.0485 (8)
H4A	0.9547	1.1031	0.2112	0.073*
O5	0.71632 (17)	0.8637 (2)	−0.1974 (3)	0.0447 (8)
H5A	0.6912	0.9350	−0.2116	0.067*
C1	0.6697 (3)	0.6144 (4)	−0.0985 (4)	0.0346 (10)
C2	0.5973 (3)	0.6892 (3)	−0.0288 (4)	0.0379 (10)
H2A	0.6162	0.7462	0.0480	0.045*
C3	0.4976 (3)	0.6797 (4)	−0.0723 (4)	0.0412 (11)
H3B	0.4488	0.7268	−0.0224	0.049*
C4	0.4712 (3)	0.5988 (4)	−0.1916 (5)	0.0436 (11)
C5	0.5414 (3)	0.5209 (4)	−0.2584 (5)	0.0521 (12)
H5B	0.5222	0.4637	−0.3348	0.063*
C6	0.6398 (3)	0.5283 (4)	−0.2113 (4)	0.0436 (11)
H6A	0.6873	0.4749	−0.2554	0.052*
C7	0.7766 (3)	0.6277 (4)	−0.0549 (4)	0.0372 (10)
C8	0.8205 (3)	0.7528 (4)	−0.0207 (4)	0.0345 (10)
C9	0.9021 (3)	0.7625 (4)	0.0842 (4)	0.0343 (10)
C10	0.9339 (3)	0.8785 (4)	0.1422 (4)	0.0393 (10)
H10A	0.9854	0.8822	0.2148	0.047*
C11	0.8876 (3)	0.9898 (4)	0.0904 (4)	0.0357 (10)
C12	0.8156 (3)	0.9871 (4)	−0.0243 (4)	0.0365 (10)
H12A	0.7892	1.0634	−0.0634	0.044*
C13	0.7836 (2)	0.8702 (4)	−0.0796 (4)	0.0329 (10)
H1W1	0.811 (4)	0.249 (5)	0.104 (6)	0.10 (2)*
H2W1	0.793 (4)	0.365 (6)	0.035 (7)	0.16 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.063 (3)	0.046 (2)	0.162 (4)	0.010 (2)	−0.006 (3)	0.011 (3)
O1	0.0485 (19)	0.050 (2)	0.086 (2)	−0.0076 (14)	−0.0287 (17)	−0.0077 (17)
O2	0.0496 (18)	0.0352 (18)	0.062 (2)	0.0080 (14)	−0.0107 (15)	0.0015 (15)
O3	0.0523 (19)	0.0393 (18)	0.070 (2)	0.0106 (13)	−0.0280 (16)	0.0062 (15)
O4	0.0457 (18)	0.0405 (18)	0.0585 (19)	−0.0029 (13)	−0.0185 (14)	−0.0044 (15)
O5	0.0508 (18)	0.0357 (16)	0.0467 (17)	0.0039 (12)	−0.0238 (14)	0.0024 (14)
C1	0.039 (3)	0.031 (2)	0.034 (2)	−0.0005 (19)	−0.006 (2)	0.002 (2)
C2	0.042 (3)	0.031 (2)	0.041 (3)	−0.001 (2)	−0.011 (2)	−0.006 (2)
C3	0.036 (3)	0.036 (2)	0.052 (3)	0.0003 (19)	−0.004 (2)	−0.001 (2)
C4	0.046 (3)	0.033 (3)	0.052 (3)	−0.010 (2)	−0.020 (2)	0.005 (2)
C5	0.057 (3)	0.041 (3)	0.058 (3)	−0.009 (2)	−0.014 (3)	−0.012 (2)
C6	0.049 (3)	0.034 (3)	0.047 (3)	−0.0037 (19)	−0.005 (2)	−0.005 (2)
C7	0.040 (3)	0.039 (3)	0.032 (2)	0.005 (2)	−0.0055 (19)	−0.001 (2)
C8	0.035 (2)	0.038 (2)	0.031 (2)	−0.0012 (18)	−0.0056 (19)	−0.0003 (19)
C9	0.030 (2)	0.036 (2)	0.036 (2)	0.0043 (18)	−0.0065 (19)	0.008 (2)
C10	0.028 (2)	0.047 (3)	0.043 (2)	0.000 (2)	−0.0145 (19)	−0.005 (2)
C11	0.031 (2)	0.035 (2)	0.041 (3)	−0.0045 (18)	−0.005 (2)	0.000 (2)
C12	0.035 (2)	0.031 (2)	0.043 (2)	0.0013 (17)	−0.007 (2)	0.006 (2)
C13	0.025 (2)	0.040 (3)	0.034 (2)	0.0014 (18)	−0.0077 (18)	0.002 (2)

Geometric parameters (Å, º) top

O1W—H1W1	0.87 (5)	C3—C4	1.384 (5)
O1W—H2W1	0.90 (6)	C3—H3B	0.93
O1—C4	1.376 (4)	C4—C5	1.374 (5)
O1—H1A	0.82	C5—C6	1.369 (5)
O2—C7	1.262 (4)	C5—H5B	0.93
O3—C9	1.362 (4)	C6—H6A	0.93
O3—H3A	0.82	C7—C8	1.451 (5)
O4—C11	1.363 (4)	C8—C13	1.408 (5)
O4—H4A	0.82	C8—C9	1.418 (4)
O5—C13	1.360 (4)	C9—C10	1.371 (5)
O5—H5A	0.82	C10—C11	1.382 (5)
C1—C2	1.387 (5)	C10—H10A	0.93
C1—C6	1.388 (5)	C11—C12	1.381 (5)
C1—C7	1.475 (5)	C12—C13	1.371 (5)
C2—C3	1.378 (4)	C12—H12A	0.93
C2—H2A	0.93

H1W1—O1W—H2W1	102 (5)	C1—C6—H6A	119.5
C4—O1—H1A	109.5	O2—C7—C8	119.5 (3)
C9—O3—H3A	109.5	O2—C7—C1	119.0 (3)
C11—O4—H4A	109.5	C8—C7—C1	121.4 (3)
C13—O5—H5A	109.5	C13—C8—C9	116.0 (3)
C2—C1—C6	118.9 (4)	C13—C8—C7	124.0 (3)
C2—C1—C7	120.4 (3)	C9—C8—C7	120.0 (3)
C6—C1—C7	120.7 (4)	O3—C9—C10	118.8 (3)
C3—C2—C1	120.6 (4)	O3—C9—C8	118.9 (3)
C3—C2—H2A	119.7	C10—C9—C8	122.2 (3)
C1—C2—H2A	119.7	C9—C10—C11	118.4 (3)
C2—C3—C4	119.0 (4)	C9—C10—H10A	120.8
C2—C3—H3B	120.5	C11—C10—H10A	120.8
C4—C3—H3B	120.5	O4—C11—C12	115.3 (3)
C5—C4—O1	118.2 (4)	O4—C11—C10	123.0 (3)
C5—C4—C3	121.0 (4)	C12—C11—C10	121.6 (4)
O1—C4—C3	120.8 (4)	C13—C12—C11	119.1 (4)
C6—C5—C4	119.4 (4)	C13—C12—H12A	120.5
C6—C5—H5B	120.3	C11—C12—H12A	120.5
C4—C5—H5B	120.3	O5—C13—C12	120.7 (3)
C5—C6—C1	120.9 (4)	O5—C13—C8	117.3 (3)
C5—C6—H6A	119.5	C12—C13—C8	121.9 (3)

C6—C1—C2—C3	−1.0 (6)	C1—C7—C8—C9	150.2 (3)
C7—C1—C2—C3	178.1 (3)	C13—C8—C9—O3	−172.0 (3)
C1—C2—C3—C4	−3.0 (6)	C7—C8—C9—O3	11.3 (5)
C2—C3—C4—C5	5.3 (6)	C13—C8—C9—C10	9.3 (5)
C2—C3—C4—O1	−175.9 (3)	C7—C8—C9—C10	−167.4 (4)
O1—C4—C5—C6	177.7 (3)	O3—C9—C10—C11	178.0 (3)
C3—C4—C5—C6	−3.4 (6)	C8—C9—C10—C11	−3.3 (6)
C4—C5—C6—C1	−0.8 (6)	C9—C10—C11—O4	177.8 (3)
C2—C1—C6—C5	3.0 (6)	C9—C10—C11—C12	−4.3 (6)
C7—C1—C6—C5	−176.2 (4)	O4—C11—C12—C13	−176.7 (3)
C2—C1—C7—O2	137.1 (4)	C10—C11—C12—C13	5.2 (6)
C6—C1—C7—O2	−43.7 (5)	C11—C12—C13—O5	−176.9 (3)
C2—C1—C7—C8	−38.6 (5)	C11—C12—C13—C8	1.4 (6)
C6—C1—C7—C8	140.5 (4)	C9—C8—C13—O5	170.0 (3)
O2—C7—C8—C13	158.0 (3)	C7—C8—C13—O5	−13.4 (5)
C1—C7—C8—C13	−26.2 (6)	C9—C8—C13—C12	−8.3 (5)
O2—C7—C8—C9	−25.5 (5)	C7—C8—C13—C12	168.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	1.79	2.529 (3)	149
O4—H4A···O3ⁱ	0.82	1.94	2.724 (4)	160
O5—H5A···O1ⁱⁱ	0.82	1.89	2.703 (3)	176
O1—H1A···O1Wⁱⁱⁱ	0.82	1.81	2.621 (5)	171
O1W—H1W1···O4^iv	0.87 (5)	2.00 (5)	2.848 (5)	167 (5)
O1W—H2W1···O2	0.90 (6)	1.87 (6)	2.751 (5)	166 (5)

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

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(4-Hydroxy­phen­yl)(2,4,6-trihydroxy­phen­yl)methanone monohydrate

Supporting information

Key indicators

checkCIF/PLATON results

(4-Hydroxyphenyl)(2,4,6-trihydroxyphenyl)methanone monohydrate