4′-Hydr­oxy-5-meth­oxy-6,7-methyl­enedioxy­isoflavone

The title compound, C₁₇H₁₂O₆, forms an infinite one-dimensional zigzag-like chain developing parallel to the b axis through O—H...O hydrogen bonds. The chains are stacked along the c axis. The crystal structure is further stabilized by weak π–π and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.040
• wR factor = 0.112
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.826     0.953
            Tmin(prime) and Tmax expected:      0.932     0.952
            RR(prime) =      0.886
            Please check that your absorption correction is appropriate.
ABSTY02_ALERT_1_C  An _exptl_absorpt_correction_type has been given without
            a literature citation. This should be contained in the
            _exptl_absorpt_process_details field.
            Absorption correction given as multi-scan
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.88
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: H.K. Fun and I.A. Razak are supervisors of Jeannie B.-J. Teh whereas M.I. Choudhary and S. Anjum are supervisors of S. Naheed in this collaborative pulication. HEJ is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

4'-Hydroxy-5-methoxy-6,7-methylenedioxyisoflavone

Crystal data

C17H12O6	F(000) = 648
Mr = 312.27	Dx = 1.513 Mg m^−3
Monoclinic, P21/c	Melting point: 501 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.0058 (7) Å	Cell parameters from 4562 reflections
b = 10.1990 (7) Å	θ = 4.2–28.3°
c = 12.7693 (8) Å	µ = 0.12 mm^−1
β = 106.922 (1)°	T = 297 K
V = 1371.27 (15) Å^3	Block, yellow
Z = 4	0.59 × 0.54 × 0.42 mm

Data collection

Bruker SMART APEX-2 CCD area-detector diffractometer	3396 independent reflections
Radiation source: fine-focus sealed tube	2784 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.33 pixels mm^-1	θmax = 28.3°, θmin = 4.2°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.866, Tmax = 0.953	l = −17→17
10654 measured 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0508P)^2 + 0.3602P] where P = (Fo^2 + 2Fc^2)/3
3396 reflections	(Δ/σ)max = 0.001
209 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.20 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	Occ. (<1)
O1	0.97231 (9)	0.91897 (11)	0.19148 (8)	0.0449 (3)
O2	1.35960 (9)	1.02816 (12)	0.45569 (9)	0.0522 (3)
O3	1.26715 (9)	1.16207 (11)	0.55665 (9)	0.0476 (3)
O4	0.98097 (9)	1.20571 (10)	0.49083 (8)	0.0468 (3)
O5	0.76718 (9)	1.13680 (12)	0.34675 (10)	0.0549 (3)
O6	0.24335 (9)	0.88775 (11)	0.07588 (10)	0.0530 (3)
H6A	0.2270	0.8144	0.0944	0.080*
C1	0.84413 (13)	0.91880 (15)	0.16074 (11)	0.0420 (3)
H1A	0.8027	0.8704	0.0989	0.050*
C2	0.77198 (12)	0.98268 (13)	0.21211 (10)	0.0349 (3)
C3	0.83264 (12)	1.06873 (13)	0.30426 (10)	0.0342 (3)
C4	1.04577 (11)	1.13094 (12)	0.43805 (10)	0.0315 (3)
C5	1.17463 (11)	1.11027 (12)	0.46869 (10)	0.0340 (3)
C6	1.23175 (12)	1.03065 (14)	0.40834 (12)	0.0385 (3)
C7	1.16697 (13)	0.96786 (15)	0.31478 (12)	0.0431 (3)
H7A	1.2071	0.9169	0.2743	0.052*
C8	1.03571 (12)	0.98578 (13)	0.28434 (10)	0.0354 (3)
C9	0.97172 (11)	1.06379 (12)	0.34165 (10)	0.0312 (3)
C10	0.63270 (12)	0.95989 (13)	0.17635 (10)	0.0351 (3)
C11	0.54407 (13)	1.06095 (14)	0.15827 (12)	0.0425 (3)
H11A	0.5720	1.1474	0.1684	0.051*
C12	0.41550 (14)	1.03496 (14)	0.12562 (13)	0.0458 (3)
H12A	0.3578	1.1039	0.1145	0.055*
C13	0.37141 (12)	0.90676 (14)	0.10916 (11)	0.0397 (3)
C14	0.45839 (13)	0.80495 (14)	0.12624 (12)	0.0434 (3)
H14A	0.4303	0.7187	0.1145	0.052*
C15	0.58714 (13)	0.83182 (14)	0.16077 (12)	0.0407 (3)
H15A	0.6447	0.7627	0.1739	0.049*
C16	1.38370 (13)	1.10114 (16)	0.55504 (13)	0.0461 (3)
H16A	1.4481	1.1672	0.5583	0.055*
H16B	1.4138	1.0433	0.6176	0.055*
C17	1.04421 (14)	1.29114 (16)	0.57713 (12)	0.0475 (3)
H17A	0.9831	1.3317	0.6072	0.071*
H17B	1.0884	1.3576	0.5494	0.071*
H17C	1.1039	1.2420	0.6332	0.071*
Cg	0.9047	0.9898	0.2491	0.010*	0.00

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0400 (5)	0.0537 (6)	0.0433 (5)	−0.0029 (4)	0.0157 (4)	−0.0180 (5)
O2	0.0318 (5)	0.0633 (7)	0.0608 (7)	0.0025 (4)	0.0124 (4)	−0.0165 (5)
O3	0.0328 (5)	0.0511 (6)	0.0542 (6)	0.0013 (4)	0.0050 (4)	−0.0167 (5)
O4	0.0375 (5)	0.0506 (6)	0.0506 (6)	0.0045 (4)	0.0101 (4)	−0.0218 (5)
O5	0.0357 (5)	0.0593 (7)	0.0672 (7)	0.0054 (5)	0.0111 (5)	−0.0288 (6)
O6	0.0373 (5)	0.0514 (6)	0.0662 (7)	−0.0065 (4)	0.0087 (5)	0.0075 (5)
C1	0.0416 (7)	0.0454 (8)	0.0384 (7)	−0.0054 (6)	0.0111 (5)	−0.0107 (6)
C2	0.0365 (6)	0.0329 (6)	0.0343 (6)	−0.0016 (5)	0.0090 (5)	−0.0007 (5)
C3	0.0346 (6)	0.0313 (6)	0.0371 (6)	0.0009 (5)	0.0111 (5)	−0.0021 (5)
C4	0.0344 (6)	0.0268 (6)	0.0350 (6)	0.0004 (4)	0.0125 (5)	−0.0009 (5)
C5	0.0341 (6)	0.0306 (6)	0.0371 (6)	−0.0021 (5)	0.0100 (5)	−0.0016 (5)
C6	0.0311 (6)	0.0389 (7)	0.0475 (7)	0.0013 (5)	0.0146 (5)	−0.0004 (6)
C7	0.0383 (7)	0.0480 (8)	0.0476 (8)	0.0014 (6)	0.0198 (6)	−0.0106 (6)
C8	0.0370 (6)	0.0359 (7)	0.0358 (6)	−0.0026 (5)	0.0147 (5)	−0.0041 (5)
C9	0.0330 (6)	0.0282 (6)	0.0338 (6)	−0.0005 (4)	0.0118 (5)	−0.0005 (5)
C10	0.0364 (6)	0.0360 (7)	0.0317 (6)	−0.0028 (5)	0.0079 (5)	−0.0014 (5)
C11	0.0416 (7)	0.0316 (7)	0.0480 (8)	−0.0026 (5)	0.0031 (6)	0.0011 (6)
C12	0.0405 (7)	0.0368 (7)	0.0538 (8)	0.0033 (6)	0.0036 (6)	0.0049 (6)
C13	0.0367 (6)	0.0437 (8)	0.0374 (6)	−0.0055 (5)	0.0087 (5)	0.0025 (6)
C14	0.0449 (7)	0.0340 (7)	0.0525 (8)	−0.0071 (5)	0.0163 (6)	−0.0033 (6)
C15	0.0415 (7)	0.0335 (7)	0.0484 (7)	0.0007 (5)	0.0150 (6)	−0.0029 (6)
C16	0.0337 (7)	0.0528 (9)	0.0499 (8)	0.0031 (6)	0.0090 (6)	−0.0047 (7)
C17	0.0480 (8)	0.0469 (8)	0.0471 (8)	−0.0005 (6)	0.0132 (6)	−0.0168 (7)

Geometric parameters (Å, º)

O1—C1	1.3497 (16)	C6—C7	1.3602 (19)
O1—C8	1.3695 (15)	C7—C8	1.3945 (18)
O2—C6	1.3604 (16)	C7—H7A	0.9300
O2—C16	1.4276 (18)	C8—C9	1.4015 (17)
O3—C5	1.3826 (15)	C10—C11	1.3915 (19)
O3—C16	1.4308 (16)	C10—C15	1.3925 (19)
O4—C4	1.3506 (15)	C11—C12	1.3795 (19)
O4—C17	1.4182 (16)	C11—H11A	0.9300
O5—C3	1.2340 (16)	C12—C13	1.389 (2)
O6—C13	1.3623 (16)	C12—H12A	0.9300
O6—H6A	0.8200	C13—C14	1.386 (2)
C1—C2	1.3374 (18)	C14—C15	1.3833 (19)
C1—H1A	0.9300	C14—H14A	0.9300
C2—C3	1.4639 (18)	C15—H15A	0.9300
C2—C10	1.4849 (17)	C16—H16A	0.9700
C3—C9	1.4657 (17)	C16—H16B	0.9700
C4—C5	1.3733 (17)	C17—H17A	0.9600
C4—C9	1.4368 (17)	C17—H17B	0.9600
C5—C6	1.3895 (18)	C17—H17C	0.9600
C1—O1—C8	118.58 (10)	C4—C9—C3	122.74 (10)
C6—O2—C16	106.61 (10)	C11—C10—C15	117.73 (12)
C5—O3—C16	105.89 (10)	C11—C10—C2	123.10 (12)
C4—O4—C17	121.58 (10)	C15—C10—C2	119.17 (12)
C13—O6—H6A	109.5	C12—C11—C10	121.04 (13)
C2—C1—O1	125.18 (12)	C12—C11—H11A	119.5
C2—C1—H1A	117.4	C10—C11—H11A	119.5
O1—C1—H1A	117.4	C11—C12—C13	120.60 (13)
C1—C2—C3	119.30 (12)	C11—C12—H12A	119.7
C1—C2—C10	118.69 (12)	C13—C12—H12A	119.7
C3—C2—C10	121.97 (11)	O6—C13—C14	123.16 (13)
O5—C3—C2	120.18 (11)	O6—C13—C12	117.73 (13)
O5—C3—C9	124.34 (12)	C14—C13—C12	119.11 (12)
C2—C3—C9	115.46 (11)	C15—C14—C13	119.89 (13)
O4—C4—C5	126.58 (11)	C15—C14—H14A	120.1
O4—C4—C9	116.52 (10)	C13—C14—H14A	120.1
C5—C4—C9	116.88 (11)	C14—C15—C10	121.62 (13)
C4—C5—O3	128.91 (11)	C14—C15—H15A	119.2
C4—C5—C6	121.88 (12)	C10—C15—H15A	119.2
O3—C5—C6	109.19 (11)	O2—C16—O3	107.68 (11)
C7—C6—O2	126.26 (12)	O2—C16—H16A	110.2
C7—C6—C5	123.80 (12)	O3—C16—H16A	110.2
O2—C6—C5	109.93 (12)	O2—C16—H16B	110.2
C6—C7—C8	114.75 (12)	O3—C16—H16B	110.2
C6—C7—H7A	122.6	H16A—C16—H16B	108.5
C8—C7—H7A	122.6	O4—C17—H17A	109.5
O1—C8—C7	113.67 (11)	O4—C17—H17B	109.5
O1—C8—C9	121.85 (11)	H17A—C17—H17B	109.5
C7—C8—C9	124.48 (12)	O4—C17—H17C	109.5
C8—C9—C4	118.16 (11)	H17A—C17—H17C	109.5
C8—C9—C3	119.03 (11)	H17B—C17—H17C	109.5
C8—O1—C1—C2	2.2 (2)	C7—C8—C9—C4	0.4 (2)
O1—C1—C2—C3	5.0 (2)	O1—C8—C9—C3	3.12 (19)
O1—C1—C2—C10	−172.63 (13)	C7—C8—C9—C3	−176.71 (13)
C1—C2—C3—O5	173.93 (14)	O4—C4—C9—C8	179.67 (11)
C10—C2—C3—O5	−8.5 (2)	C5—C4—C9—C8	−1.83 (17)
C1—C2—C3—C9	−7.72 (18)	O4—C4—C9—C3	−3.30 (18)
C10—C2—C3—C9	169.86 (11)	C5—C4—C9—C3	175.20 (12)
C17—O4—C4—C5	10.9 (2)	O5—C3—C9—C8	−177.92 (14)
C17—O4—C4—C9	−170.75 (12)	C2—C3—C9—C8	3.81 (17)
O4—C4—C5—O3	−1.9 (2)	O5—C3—C9—C4	5.1 (2)
C9—C4—C5—O3	179.80 (12)	C2—C3—C9—C4	−173.20 (11)
O4—C4—C5—C6	179.74 (13)	C1—C2—C10—C11	−133.41 (15)
C9—C4—C5—C6	1.42 (19)	C3—C2—C10—C11	49.00 (19)
C16—O3—C5—C4	175.85 (14)	C1—C2—C10—C15	47.20 (18)
C16—O3—C5—C6	−5.60 (15)	C3—C2—C10—C15	−130.39 (14)
C16—O2—C6—C7	−176.64 (15)	C15—C10—C11—C12	−0.2 (2)
C16—O2—C6—C5	4.60 (16)	C2—C10—C11—C12	−179.65 (13)
C4—C5—C6—C7	0.5 (2)	C10—C11—C12—C13	−0.5 (2)
O3—C5—C6—C7	−178.13 (13)	C11—C12—C13—O6	−179.35 (13)
C4—C5—C6—O2	179.33 (12)	C11—C12—C13—C14	0.2 (2)
O3—C5—C6—O2	0.66 (16)	O6—C13—C14—C15	−179.58 (13)
O2—C6—C7—C8	179.49 (14)	C12—C13—C14—C15	0.9 (2)
C5—C6—C7—C8	−1.9 (2)	C13—C14—C15—C10	−1.7 (2)
C1—O1—C8—C7	173.50 (13)	C11—C10—C15—C14	1.4 (2)
C1—O1—C8—C9	−6.35 (19)	C2—C10—C15—C14	−179.20 (12)
C6—C7—C8—O1	−178.43 (12)	C6—O2—C16—O3	−8.01 (16)
C6—C7—C8—C9	1.4 (2)	C5—O3—C16—O2	8.34 (16)
O1—C8—C9—C4	−179.74 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O4^i	0.82	2.49	3.0072 (15)	122
O6—H6A···O5^i	0.82	1.96	2.7581 (17)	166
C17—H17C···Cg^ii	0.96	2.82	3.567	136

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