Bergenin monohydrate, a constituent of Hurmiria balsamifera, at 120 K

The title compound, 3,4,4a,10b-tetra­hydro-3,4,8,10-tetra­hydroxy-2-(hydroxy­methyl)-9-methoxy­pyrano­[3,2-c][2]­benzo­pyran-6(2H)-one monohydrate, C₁₄H₁₆O₉·H₂O, crystallized in space group P2₁2₁2₁ from methanol. The data collection was made at low temperature and the results obtained agree with those reported in another publication for the same compound determined at room temperature [Shang-Zhen, Hua, Xu-Wei, Zhong-Yuan & Guo-Zhi (1989). J. Struct. Chem. 8, 305-310]. However, there are small differences in the cell constants and some geometrical parameters.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.037
• wR factor = 0.129
• Data-to-parameter ratio = 8.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.53
         From the CIF: _reflns_number_total               1943
         Count of symmetry unique reflns         1951
         Completeness (_total/calc)             99.59%
         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
          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.

---

Computing details

Data collection: COLLECT (Nonius, 1999); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Crystal-Structure Analysis at low temperature of Bergenin monohydrated, a Constituent of Hurmiria Balsamifera.

Crystal data

C14H16O9·H2O	Dx = 1.564 Mg m^−3
Mr = 346.28	Mo Kα radiation, λ = 0.71070 Å
Orthorhombic, P212121	Cell parameters from 1951 reflections
a = 7.484 (2) Å	θ = 1.0–27.5°
b = 13.901 (3) Å	µ = 0.14 mm^−1
c = 14.132 (4) Å	T = 120 K
V = 1470.2 (7) Å^3	Prism, colorless
Z = 4	0.28 × 0.16 × 0.14 mm
F(000) = 728

Data collection

Nonius KappaCCD diffractometer	1713 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Horizonally mounted graphite crystal monochromator	θmax = 27.5°, θmin = 2.1°
Detector resolution: 9 pixels mm^-1	h = 0→9
φ scans, and ω scans winth κ offsets	k = 0→17
1943 measured reflections	l = 0→18
1943 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H-atom parameters constrained
S = 1.26	w = 1/[σ^2(Fo^2) + (0.076P)^2 + 0.0815P] where P = (Fo^2 + 2Fc^2)/3
1943 reflections	(Δ/σ)max = 0.001
225 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

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	0.4384 (3)	0.24704 (12)	0.61310 (13)	0.0185 (4)
H1'	0.4004	0.2743	0.5640	0.028*
O2	0.7872 (3)	0.18240 (13)	0.54694 (14)	0.0180 (4)
H2'	0.8478	0.1392	0.5733	0.027*
O3	0.7632 (3)	0.04125 (13)	0.40163 (14)	0.0202 (4)
O4	0.9048 (3)	−0.04419 (14)	0.29509 (16)	0.0267 (5)
O5	0.5762 (3)	−0.36949 (13)	0.29338 (15)	0.0229 (5)
H5'	0.6639	−0.3691	0.2563	0.034*
O6	0.2837 (3)	−0.34064 (13)	0.39674 (14)	0.0193 (4)
O7	0.2053 (3)	−0.16380 (14)	0.47015 (15)	0.0234 (5)
H7'	0.2042	−0.1105	0.4982	0.035*
O8	0.3505 (3)	−0.00170 (12)	0.53581 (13)	0.0163 (4)
O9	0.0116 (3)	0.04804 (14)	0.62186 (16)	0.0219 (5)
H9'	0.0042	−0.0091	0.6409	0.033*
C1	0.3069 (4)	0.09506 (17)	0.56559 (19)	0.0153 (6)
H1	0.2460	0.1297	0.5126	0.018*
C2	0.4794 (4)	0.14889 (18)	0.59235 (19)	0.0158 (5)
H2	0.5290	0.1187	0.6510	0.019*
C3	0.6218 (4)	0.14291 (18)	0.5150 (2)	0.0160 (5)
H3	0.5799	0.1823	0.4601	0.019*
C4	0.6423 (4)	0.04000 (18)	0.48151 (19)	0.0159 (5)
H4	0.6940	−0.0002	0.5334	0.019*
C5	0.7796 (4)	−0.04043 (19)	0.3503 (2)	0.0195 (6)
C6	0.6445 (4)	−0.11722 (19)	0.3619 (2)	0.0180 (5)
C7	0.6766 (4)	−0.20623 (19)	0.3187 (2)	0.0185 (6)
H7	0.7813	−0.2160	0.2819	0.022*
C8	0.5532 (4)	−0.28011 (19)	0.3303 (2)	0.0185 (6)
C9	0.3976 (4)	−0.26469 (18)	0.3826 (2)	0.0168 (5)
C10	0.3630 (4)	−0.17403 (19)	0.4227 (2)	0.0178 (6)
C11	0.4879 (4)	−0.10000 (19)	0.41363 (19)	0.0165 (6)
C12	0.4616 (4)	0.00020 (18)	0.45281 (18)	0.0151 (5)
H12	0.4064	0.0424	0.4035	0.018*
C13	0.1221 (5)	−0.3327 (2)	0.3428 (3)	0.0326 (8)
H13A	0.0520	−0.2780	0.3661	0.049*
H13B	0.0522	−0.3919	0.3496	0.049*
H13C	0.1515	−0.3227	0.2760	0.049*
C14	0.1804 (4)	0.08728 (19)	0.6490 (2)	0.0182 (6)
H14A	0.2348	0.0458	0.6981	0.022*
H14B	0.1620	0.1519	0.6768	0.022*
O1W	0.1539 (3)	0.10674 (14)	0.32174 (15)	0.0215 (5)
H11W	0.0914	0.1562	0.3412	0.042 (11)*
H12W	0.0678	0.0601	0.3201	0.052 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0210 (10)	0.0132 (8)	0.0214 (10)	0.0020 (8)	−0.0015 (9)	−0.0015 (7)
O2	0.0148 (9)	0.0163 (9)	0.0230 (10)	−0.0024 (8)	−0.0021 (8)	0.0003 (7)
O3	0.0209 (10)	0.0173 (9)	0.0223 (10)	−0.0033 (8)	0.0083 (9)	−0.0044 (8)
O4	0.0252 (11)	0.0222 (10)	0.0328 (12)	−0.0060 (9)	0.0122 (10)	−0.0083 (8)
O5	0.0234 (11)	0.0126 (9)	0.0326 (12)	0.0001 (8)	0.0078 (10)	−0.0039 (8)
O6	0.0193 (10)	0.0148 (9)	0.0237 (10)	−0.0052 (8)	−0.0013 (9)	0.0014 (7)
O7	0.0175 (10)	0.0241 (10)	0.0288 (11)	−0.0038 (9)	0.0074 (9)	−0.0068 (9)
O8	0.0174 (9)	0.0124 (8)	0.0189 (9)	0.0002 (8)	0.0037 (8)	−0.0021 (7)
O9	0.0164 (10)	0.0180 (9)	0.0314 (11)	−0.0008 (8)	−0.0004 (9)	0.0041 (8)
C1	0.0169 (13)	0.0099 (11)	0.0191 (13)	0.0032 (10)	0.0008 (11)	−0.0017 (9)
C2	0.0186 (13)	0.0118 (12)	0.0171 (12)	0.0002 (10)	−0.0009 (11)	−0.0008 (9)
C3	0.0149 (13)	0.0132 (11)	0.0198 (13)	−0.0024 (10)	−0.0005 (11)	0.0001 (10)
C4	0.0155 (12)	0.0155 (12)	0.0167 (12)	−0.0022 (11)	0.0035 (11)	−0.0002 (10)
C5	0.0203 (14)	0.0165 (12)	0.0217 (13)	−0.0005 (11)	0.0035 (12)	−0.0012 (10)
C6	0.0170 (13)	0.0168 (12)	0.0201 (13)	−0.0017 (11)	0.0012 (12)	−0.0002 (10)
C7	0.0183 (14)	0.0180 (12)	0.0192 (13)	0.0014 (11)	0.0016 (12)	−0.0010 (10)
C8	0.0221 (15)	0.0153 (12)	0.0180 (13)	0.0029 (11)	−0.0010 (12)	0.0002 (10)
C9	0.0175 (13)	0.0138 (11)	0.0191 (13)	−0.0028 (10)	−0.0007 (11)	0.0011 (10)
C10	0.0165 (13)	0.0195 (12)	0.0173 (13)	−0.0009 (11)	0.0009 (11)	−0.0012 (11)
C11	0.0185 (13)	0.0168 (12)	0.0141 (12)	−0.0015 (10)	−0.0014 (11)	−0.0005 (9)
C12	0.0159 (13)	0.0149 (12)	0.0145 (12)	−0.0007 (11)	0.0019 (10)	−0.0004 (9)
C13	0.0289 (17)	0.0294 (16)	0.0396 (19)	−0.0128 (14)	−0.0123 (15)	0.0067 (14)
C14	0.0150 (14)	0.0188 (13)	0.0206 (14)	−0.0004 (10)	0.0001 (11)	−0.0015 (10)
O1W	0.0191 (10)	0.0181 (9)	0.0274 (11)	0.0007 (8)	0.0027 (9)	0.0009 (8)

Geometric parameters (Å, º)

O1—C2	1.429 (3)	C3—C4	1.515 (3)
O1—H1'	0.8400	C3—H3	1.0000
O2—C3	1.428 (3)	C4—C12	1.517 (4)
O2—H2'	0.8400	C4—H4	1.0000
O3—C5	1.353 (3)	C5—C6	1.480 (4)
O3—C4	1.447 (3)	C6—C7	1.401 (4)
O4—C5	1.221 (4)	C6—C11	1.402 (4)
O5—C8	1.358 (3)	C7—C8	1.391 (4)
O5—H5'	0.8400	C7—H7	0.9500
O6—C9	1.372 (3)	C8—C9	1.396 (4)
O6—C13	1.434 (4)	C9—C10	1.406 (4)
O7—C10	1.364 (3)	C10—C11	1.396 (4)
O7—H7'	0.8400	C11—C12	1.512 (3)
O8—C12	1.438 (3)	C12—H12	1.0000
O8—C1	1.447 (3)	C13—H13A	0.9800
O9—C14	1.429 (3)	C13—H13B	0.9800
O9—H9'	0.8400	C13—H13C	0.9800
C1—C14	1.516 (4)	C14—H14A	0.9900
C1—C2	1.539 (4)	C14—H14B	0.9900
C1—H1	1.0000	O1W—H11W	0.8760
C2—C3	1.529 (4)	O1W—H12W	0.9142
C2—H2	1.0000
C2—O1—H1'	109.5	C7—C6—C5	118.1 (2)
C3—O2—H2'	109.5	C11—C6—C5	120.4 (2)
C5—O3—C4	117.7 (2)	C8—C7—C6	119.1 (3)
C8—O5—H5'	109.5	C8—C7—H7	120.4
C9—O6—C13	112.8 (2)	C6—C7—H7	120.4
C10—O7—H7'	109.5	O5—C8—C7	123.1 (3)
C12—O8—C1	110.52 (19)	O5—C8—C9	116.7 (2)
C14—O9—H9'	109.5	C7—C8—C9	120.2 (2)
O8—C1—C14	107.50 (19)	O6—C9—C8	118.5 (2)
O8—C1—C2	109.5 (2)	O6—C9—C10	121.1 (2)
C14—C1—C2	111.6 (2)	C8—C9—C10	120.3 (2)
O8—C1—H1	109.4	O7—C10—C11	123.2 (2)
C14—C1—H1	109.4	O7—C10—C9	116.8 (2)
C2—C1—H1	109.4	C11—C10—C9	120.0 (3)
O1—C2—C3	110.4 (2)	C10—C11—C6	118.8 (2)
O1—C2—C1	109.5 (2)	C10—C11—C12	123.9 (2)
C3—C2—C1	112.5 (2)	C6—C11—C12	117.2 (2)
O1—C2—H2	108.1	O8—C12—C11	110.9 (2)
C3—C2—H2	108.1	O8—C12—C4	107.7 (2)
C1—C2—H2	108.1	C11—C12—C4	108.5 (2)
O2—C3—C4	112.0 (2)	O8—C12—H12	109.9
O2—C3—C2	110.9 (2)	C11—C12—H12	109.9
C4—C3—C2	110.2 (2)	C4—C12—H12	109.9
O2—C3—H3	107.9	O6—C13—H13A	109.5
C4—C3—H3	107.9	O6—C13—H13B	109.5
C2—C3—H3	107.9	H13A—C13—H13B	109.5
O3—C4—C3	107.2 (2)	O6—C13—H13C	109.5
O3—C4—C12	110.7 (2)	H13A—C13—H13C	109.5
C3—C4—C12	109.7 (2)	H13B—C13—H13C	109.5
O3—C4—H4	109.7	O9—C14—C1	111.8 (2)
C3—C4—H4	109.7	O9—C14—H14A	109.3
C12—C4—H4	109.7	C1—C14—H14A	109.3
O4—C5—O3	116.6 (2)	O9—C14—H14B	109.3
O4—C5—C6	124.4 (2)	C1—C14—H14B	109.3
O3—C5—C6	119.0 (2)	H14A—C14—H14B	107.9
C7—C6—C11	121.5 (2)	H11W—O1W—H12W	100.8
C12—O8—C1—C14	176.4 (2)	O5—C8—C9—O6	2.8 (4)
C12—O8—C1—C2	−62.3 (3)	C7—C8—C9—O6	−176.6 (3)
O8—C1—C2—O1	174.54 (19)	O5—C8—C9—C10	−179.5 (3)
C14—C1—C2—O1	−66.6 (3)	C7—C8—C9—C10	1.1 (4)
O8—C1—C2—C3	51.4 (3)	O6—C9—C10—O7	−4.5 (4)
C14—C1—C2—C3	170.3 (2)	C8—C9—C10—O7	177.9 (2)
O1—C2—C3—O2	65.0 (3)	O6—C9—C10—C11	174.9 (2)
C1—C2—C3—O2	−172.3 (2)	C8—C9—C10—C11	−2.7 (4)
O1—C2—C3—C4	−170.4 (2)	O7—C10—C11—C6	−178.8 (3)
C1—C2—C3—C4	−47.8 (3)	C9—C10—C11—C6	1.8 (4)
C5—O3—C4—C3	−169.6 (2)	O7—C10—C11—C12	−1.6 (4)
C5—O3—C4—C12	−50.0 (3)	C9—C10—C11—C12	179.0 (3)
O2—C3—C4—O3	−62.4 (3)	C7—C6—C11—C10	0.7 (4)
C2—C3—C4—O3	173.6 (2)	C5—C6—C11—C10	179.7 (3)
O2—C3—C4—C12	177.4 (2)	C7—C6—C11—C12	−176.7 (3)
C2—C3—C4—C12	53.4 (3)	C5—C6—C11—C12	2.3 (4)
C4—O3—C5—O4	−166.7 (2)	C1—O8—C12—C11	−172.6 (2)
C4—O3—C5—C6	15.2 (4)	C1—O8—C12—C4	68.8 (2)
O4—C5—C6—C7	10.9 (4)	C10—C11—C12—O8	29.4 (4)
O3—C5—C6—C7	−171.2 (3)	C6—C11—C12—O8	−153.3 (2)
O4—C5—C6—C11	−168.2 (3)	C10—C11—C12—C4	147.6 (3)
O3—C5—C6—C11	9.8 (4)	C6—C11—C12—C4	−35.2 (3)
C11—C6—C7—C8	−2.3 (4)	O3—C4—C12—O8	178.3 (2)
C5—C6—C7—C8	178.7 (3)	C3—C4—C12—O8	−63.6 (3)
C6—C7—C8—O5	−177.9 (3)	O3—C4—C12—C11	58.1 (3)
C6—C7—C8—C9	1.4 (4)	C3—C4—C12—C11	176.3 (2)
C13—O6—C9—C8	−107.9 (3)	O8—C1—C14—O9	−67.1 (3)
C13—O6—C9—C10	74.5 (3)	C2—C1—C14—O9	172.8 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1′···O2^i	0.84	1.88	2.714 (2)	170
O2—H2′···O9^ii	0.84	1.89	2.725 (2)	171
O5—H5′···O1W^iii	0.84	1.78	2.613 (2)	169
O7—H7′···O8	0.84	1.94	2.668 (2)	144
O9—H9′···O5^iv	0.84	2.00	2.799 (2)	158
O1W—H11W···O1^i	0.88	1.88	2.753 (2)	174
O1W—H12W···O3^v	0.91	2.57	3.265 (2)	133
O1W—H12W···O4^v	0.91	1.93	2.834 (2)	170
C2—H2···O4^vi	1.00	2.34	3.327 (3)	170
C4—H4···O6^vii	1.00	2.51	3.427 (2)	152
C12—H12···O1W	1.00	2.39	3.306 (3)	152
C13—H13A···O7	0.98	2.44	3.019 (3)	117

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