5,7-Dihydr­oxy-8-meth­oxy-2-phenyl-4H-chromen-4-one monohydrate

In the crystal structure of the title compound, C₁₆H₁₂O₅·H₂O, the water O atom is involved in inter­molecular hydrogen bonds which link the mol­ecules into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.054
• wR factor = 0.135
• Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C16 H14 O6
            Atom count from _chemical_formula_moiety:C16 H32 O5
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.30
           From the CIF: _reflns_number_total               1825
           Count of symmetry unique reflns         1915
           Completeness (_total/calc)             95.30%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 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
   0 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
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLUTON (Spek, 2003); software used to prepare material for publication: SHELXL97.

5,7-Dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one monohydrate

Crystal data

C16H12O5·H2O	F(000) = 632
Mr = 302.27	Dx = 1.393 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1825 reflections
a = 4.7160 (9) Å	θ = 3.5–27.3°
b = 16.551 (3) Å	µ = 0.11 mm^−1
c = 18.466 (4) Å	T = 298 K
V = 1441.4 (5) Å^3	Prism, yellow
Z = 4	0.40 × 0.10 × 0.10 mm

Data collection

MAC DIP 2030K diffractometer	1801 reflections with I > 2σ(I)
Radiation source: rotate anode	Rint = 0.040
Graphite monochromator	θmax = 27.3°, θmin = 3.5°
Detector resolution: 0 pixels mm^-1	h = 0→5
ω scans	k = −21→21
4404 measured reflections	l = −23→23
1825 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: geom & difmap
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.0494P)^2 + 0.6551P] where P = (Fo^2 + 2Fc^2)/3
S = 1.23	(Δ/σ)max = 0.001
1825 reflections	Δρmax = 0.16 e Å^−3
208 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.059 (11)

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
O1	0.0501 (5)	0.42824 (13)	0.27703 (10)	0.0429 (5)
O2	−0.3595 (6)	0.63101 (13)	0.34772 (12)	0.0561 (7)
O3	−0.6468 (6)	0.63385 (14)	0.22700 (13)	0.0596 (7)
H3A	−0.5969	0.6487	0.2674	0.089*
O4	−0.4502 (7)	0.43054 (15)	0.05499 (11)	0.0585 (7)
H4A	−0.3521	0.3902	0.0491	0.088*
O5	−0.0475 (6)	0.36079 (13)	0.14443 (11)	0.0496 (6)
C2	0.1091 (7)	0.46033 (18)	0.34343 (15)	0.0420 (7)
C3	−0.0228 (8)	0.52753 (19)	0.36774 (17)	0.0468 (8)
H3B	0.0241	0.5476	0.4132	0.056*
C4	−0.2323 (8)	0.56867 (18)	0.32559 (15)	0.0437 (7)
C5	−0.4966 (8)	0.56685 (19)	0.20767 (16)	0.0455 (8)
C6	−0.5487 (9)	0.5315 (2)	0.14144 (16)	0.0483 (8)
H6A	−0.6834	0.5535	0.1104	0.058*
C7	−0.3976 (8)	0.46241 (18)	0.12123 (15)	0.0462 (8)
C8	−0.1989 (8)	0.42744 (17)	0.16707 (15)	0.0419 (7)
C9	−0.1491 (7)	0.46422 (17)	0.23386 (15)	0.0405 (7)
C10	−0.2958 (7)	0.53364 (17)	0.25578 (15)	0.0404 (7)
C11	−0.1547 (13)	0.2863 (2)	0.1725 (2)	0.0723 (13)
H11A	−0.0413	0.2424	0.1549	0.108*
H11B	−0.3475	0.2792	0.1571	0.108*
H11C	−0.1473	0.2874	0.2245	0.108*
C1'	0.3207 (7)	0.41227 (18)	0.38255 (16)	0.0426 (7)
C2'	0.4376 (9)	0.3426 (2)	0.35233 (17)	0.0526 (8)
H2'A	0.3800	0.3260	0.3065	0.063*
C3'	0.6377 (9)	0.2980 (2)	0.3895 (2)	0.0576 (9)
H3'A	0.7145	0.2518	0.3685	0.069*
C4'	0.7243 (9)	0.3219 (2)	0.4580 (2)	0.0590 (9)
H4'A	0.8602	0.2922	0.4830	0.071*
C5'	0.6069 (9)	0.3903 (2)	0.4889 (2)	0.0603 (10)
H5'A	0.6628	0.4058	0.5351	0.072*
C6'	0.4088 (9)	0.4356 (2)	0.45236 (17)	0.0533 (8)
H6'A	0.3332	0.4817	0.4737	0.064*
OW	−0.2104 (7)	0.29879 (17)	−0.01382 (14)	0.0599 (7)
HWA	−0.183 (12)	0.322 (3)	−0.057 (3)	0.093 (16)*
HWB	−0.043 (19)	0.278 (4)	0.001 (4)	0.16 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0503 (12)	0.0458 (11)	0.0325 (9)	0.0020 (11)	−0.0042 (10)	−0.0013 (8)
O2	0.0729 (17)	0.0454 (12)	0.0500 (12)	0.0076 (13)	−0.0032 (13)	−0.0104 (9)
O3	0.0764 (18)	0.0509 (13)	0.0515 (13)	0.0176 (14)	−0.0060 (14)	−0.0017 (10)
O4	0.0801 (19)	0.0601 (13)	0.0353 (10)	0.0070 (15)	−0.0104 (13)	−0.0050 (10)
O5	0.0637 (15)	0.0444 (11)	0.0406 (11)	0.0031 (12)	0.0058 (11)	−0.0037 (9)
C2	0.0449 (17)	0.0485 (15)	0.0327 (13)	−0.0058 (14)	0.0011 (13)	−0.0008 (11)
C3	0.0536 (19)	0.0497 (16)	0.0370 (14)	−0.0043 (16)	−0.0023 (14)	−0.0039 (12)
C4	0.0522 (19)	0.0401 (14)	0.0389 (14)	−0.0037 (15)	0.0050 (14)	−0.0040 (12)
C5	0.0548 (19)	0.0412 (15)	0.0403 (14)	0.0008 (16)	0.0037 (15)	0.0064 (12)
C6	0.058 (2)	0.0505 (17)	0.0361 (14)	−0.0010 (17)	−0.0056 (15)	0.0061 (12)
C7	0.064 (2)	0.0430 (14)	0.0317 (13)	−0.0058 (16)	−0.0006 (15)	0.0025 (11)
C8	0.0528 (19)	0.0379 (13)	0.0349 (13)	−0.0048 (14)	0.0041 (13)	−0.0010 (11)
C9	0.0460 (17)	0.0410 (14)	0.0346 (13)	−0.0022 (14)	0.0035 (13)	0.0023 (11)
C10	0.0489 (17)	0.0373 (13)	0.0348 (13)	−0.0040 (13)	0.0024 (13)	−0.0002 (11)
C11	0.108 (4)	0.0390 (16)	0.070 (2)	0.003 (2)	0.015 (3)	−0.0006 (16)
C1'	0.0432 (16)	0.0474 (15)	0.0372 (13)	−0.0048 (14)	0.0030 (14)	0.0015 (12)
C2'	0.058 (2)	0.0568 (18)	0.0431 (16)	0.0051 (17)	−0.0029 (17)	−0.0031 (14)
C3'	0.059 (2)	0.0553 (18)	0.0583 (19)	0.0081 (19)	−0.0004 (19)	0.0004 (16)
C4'	0.050 (2)	0.068 (2)	0.060 (2)	0.0011 (19)	−0.0085 (18)	0.0135 (17)
C5'	0.064 (3)	0.070 (2)	0.0468 (17)	−0.009 (2)	−0.0136 (18)	0.0026 (16)
C6'	0.058 (2)	0.0592 (18)	0.0428 (15)	−0.0012 (18)	−0.0041 (16)	−0.0025 (15)
OW	0.0726 (19)	0.0657 (15)	0.0413 (12)	0.0046 (15)	0.0042 (14)	0.0036 (11)

Geometric parameters (Å, º)

O1—C2	1.365 (3)	C8—C9	1.395 (4)
O1—C9	1.369 (4)	C9—C10	1.401 (4)
O2—C4	1.262 (4)	C11—H11A	0.9600
O3—C5	1.363 (4)	C11—H11B	0.9600
O3—H3A	0.8200	C11—H11C	0.9600
O4—C7	1.355 (3)	C1'—C2'	1.394 (5)
O4—H4A	0.8200	C1'—C6'	1.409 (4)
O5—C8	1.379 (4)	C2'—C3'	1.381 (5)
O5—C11	1.429 (4)	C2'—H2'A	0.9300
C2—C3	1.351 (4)	C3'—C4'	1.388 (5)
C2—C1'	1.466 (4)	C3'—H3'A	0.9300
C3—C4	1.430 (5)	C4'—C5'	1.383 (5)
C3—H3B	0.9300	C4'—H4'A	0.9300
C4—C10	1.445 (4)	C5'—C6'	1.376 (5)
C5—C6	1.378 (4)	C5'—H5'A	0.9300
C5—C10	1.410 (4)	C6'—H6'A	0.9300
C6—C7	1.398 (5)	OW—HWA	0.90 (5)
C6—H6A	0.9300	OW—HWB	0.90 (9)
C7—C8	1.389 (5)
C2—O1—C9	119.6 (2)	C9—C10—C5	118.0 (3)
C5—O3—H3A	109.5	C9—C10—C4	119.0 (3)
C7—O4—H4A	109.5	C5—C10—C4	123.0 (3)
C8—O5—C11	113.4 (3)	O5—C11—H11A	109.5
C3—C2—O1	121.7 (3)	O5—C11—H11B	109.5
C3—C2—C1'	126.6 (3)	H11A—C11—H11B	109.5
O1—C2—C1'	111.7 (3)	O5—C11—H11C	109.5
C2—C3—C4	121.9 (3)	H11A—C11—H11C	109.5
C2—C3—H3B	119.0	H11B—C11—H11C	109.5
C4—C3—H3B	119.0	C2'—C1'—C6'	118.5 (3)
O2—C4—C3	122.8 (3)	C2'—C1'—C2	121.4 (3)
O2—C4—C10	121.2 (3)	C6'—C1'—C2	120.2 (3)
C3—C4—C10	116.0 (3)	C3'—C2'—C1'	120.9 (3)
O3—C5—C6	119.0 (3)	C3'—C2'—H2'A	119.5
O3—C5—C10	120.1 (3)	C1'—C2'—H2'A	119.5
C6—C5—C10	120.9 (3)	C2'—C3'—C4'	120.1 (4)
C5—C6—C7	119.6 (3)	C2'—C3'—H3'A	119.9
C5—C6—H6A	120.2	C4'—C3'—H3'A	119.9
C7—C6—H6A	120.2	C5'—C4'—C3'	119.4 (4)
O4—C7—C8	120.8 (3)	C5'—C4'—H4'A	120.3
O4—C7—C6	117.8 (3)	C3'—C4'—H4'A	120.3
C8—C7—C6	121.5 (3)	C6'—C5'—C4'	121.1 (3)
O5—C8—C7	119.9 (3)	C6'—C5'—H5'A	119.4
O5—C8—C9	122.0 (3)	C4'—C5'—H5'A	119.4
C7—C8—C9	118.1 (3)	C5'—C6'—C1'	120.0 (3)
O1—C9—C8	116.2 (3)	C5'—C6'—H6'A	120.0
O1—C9—C10	121.8 (3)	C1'—C6'—H6'A	120.0
C8—C9—C10	122.0 (3)	HWA—OW—HWB	108 (6)
C9—O1—C2—C3	−0.6 (4)	C8—C9—C10—C5	−0.8 (4)
C9—O1—C2—C1'	178.2 (3)	O1—C9—C10—C4	0.8 (4)
O1—C2—C3—C4	0.3 (5)	C8—C9—C10—C4	−179.7 (3)
C1'—C2—C3—C4	−178.3 (3)	O3—C5—C10—C9	179.3 (3)
C2—C3—C4—O2	179.3 (3)	C6—C5—C10—C9	0.7 (5)
C2—C3—C4—C10	0.5 (5)	O3—C5—C10—C4	−1.8 (5)
O3—C5—C6—C7	−179.5 (3)	C6—C5—C10—C4	179.6 (3)
C10—C5—C6—C7	−0.9 (5)	O2—C4—C10—C9	−179.8 (3)
C5—C6—C7—O4	−178.5 (3)	C3—C4—C10—C9	−1.0 (4)
C5—C6—C7—C8	1.2 (5)	O2—C4—C10—C5	1.3 (5)
C11—O5—C8—C7	−100.4 (4)	C3—C4—C10—C5	−179.9 (3)
C11—O5—C8—C9	83.0 (4)	C3—C2—C1'—C2'	178.5 (4)
O4—C7—C8—O5	1.7 (5)	O1—C2—C1'—C2'	−0.3 (4)
C6—C7—C8—O5	−178.0 (3)	C3—C2—C1'—C6'	−1.1 (5)
O4—C7—C8—C9	178.4 (3)	O1—C2—C1'—C6'	−179.8 (3)
C6—C7—C8—C9	−1.3 (5)	C6'—C1'—C2'—C3'	−0.8 (5)
C2—O1—C9—C8	−179.5 (3)	C2—C1'—C2'—C3'	179.7 (3)
C2—O1—C9—C10	0.0 (4)	C1'—C2'—C3'—C4'	0.3 (6)
O5—C8—C9—O1	−2.8 (4)	C2'—C3'—C4'—C5'	0.5 (6)
C7—C8—C9—O1	−179.4 (3)	C3'—C4'—C5'—C6'	−1.0 (6)
O5—C8—C9—C10	177.7 (3)	C4'—C5'—C6'—C1'	0.6 (6)
C7—C8—C9—C10	1.1 (5)	C2'—C1'—C6'—C5'	0.3 (5)
O1—C9—C10—C5	179.7 (3)	C2—C1'—C6'—C5'	179.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2	0.82	1.88	2.609 (3)	147
O4—H4A···OW	0.82	2.02	2.766 (4)	151
OW—HWA···O2^i	0.90 (5)	1.93 (5)	2.828 (3)	177 (5)
OW—HWB···OW^ii	0.90 (9)	2.03 (8)	2.903 (3)	161 (7)

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