5,7-Dimeth­oxy-2-phenyl-4H-1-benzopyran-4-one chloro­form solvate

The title compound, C₁₇H₁₄O₄·CHCl₃, was isolated from the rhizomes of Kaempferia parviflora. The benzopyran-4-one ring system and the phenyl substituent are approximately coplanar. The crystal structure is stabilized by π–π stacking inter­actions between the benzopyran-4-one ring system of inversion-related mol­ecules stacked along the c axis, and C—H...O and C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.102
• Data-to-parameter ratio = 22.8

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        C18
PLAT432_ALERT_2_C Short Inter X...Y Contact  O2     ..  C18     ..       2.92 Ang.

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 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.

   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

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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).

5,7-dimethoxy-2-phenyl-4H-1-benzopyran-4-one chloroform solvate

Crystal data

C17H14O4·CHCl3	F(000) = 824
Mr = 401.65	Dx = 1.494 Mg m^−3
Monoclinic, P21/c	Melting point = 425–426 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.4036 (3) Å	Cell parameters from 9157 reflections
b = 18.8997 (5) Å	θ = 1.5–30.0°
c = 7.1512 (2) Å	µ = 0.53 mm^−1
β = 99.675 (1)°	T = 100 K
V = 1785.80 (8) Å^3	Block, colourless
Z = 4	0.53 × 0.47 × 0.39 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	5194 independent reflections
Radiation source: fine-focus sealed tube	4765 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 1.5°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −26→26
Tmin = 0.761, Tmax = 0.812	l = −10→10
57712 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0369P)^2 + 2.0228P] where P = (Fo^2 + 2Fc^2)/3
5194 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 1.03 e Å^−3
0 restraints	Δρmin = −1.12 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
Cl1	0.45340 (3)	0.46077 (2)	0.71137 (7)	0.02927 (10)
Cl2	0.36470 (3)	0.32299 (3)	0.61591 (9)	0.04718 (15)
Cl3	0.41254 (5)	0.36735 (4)	1.00642 (9)	0.05686 (18)
O1	0.13789 (7)	0.53187 (5)	0.35861 (13)	0.01333 (17)
O2	−0.15010 (7)	0.60949 (5)	0.26086 (16)	0.0191 (2)
O3	0.04160 (8)	0.30653 (5)	0.10187 (15)	0.0179 (2)
O4	−0.21047 (7)	0.48070 (5)	0.12310 (14)	0.01603 (19)
C1	0.06092 (9)	0.48851 (6)	0.27559 (17)	0.0119 (2)
C2	0.09367 (10)	0.42151 (7)	0.23207 (18)	0.0137 (2)
H2A	0.1618	0.4093	0.2574	0.016*
C3	0.02100 (10)	0.37386 (7)	0.14969 (18)	0.0136 (2)
C4	−0.08193 (10)	0.39256 (7)	0.11085 (18)	0.0139 (2)
H4A	−0.1296	0.3598	0.0551	0.017*
C5	−0.11236 (9)	0.45948 (7)	0.15537 (17)	0.0125 (2)
C6	−0.04021 (9)	0.51055 (6)	0.24036 (17)	0.0119 (2)
C7	−0.06419 (9)	0.58347 (7)	0.28714 (18)	0.0131 (2)
C8	0.02246 (10)	0.62583 (7)	0.36945 (18)	0.0139 (2)
H8A	0.0122	0.6729	0.3988	0.017*
C9	0.11719 (9)	0.59957 (6)	0.40490 (17)	0.0120 (2)
C10	0.20883 (9)	0.63813 (7)	0.49182 (17)	0.0122 (2)
C11	0.20114 (10)	0.70554 (7)	0.57035 (18)	0.0147 (2)
H11A	0.1378	0.7255	0.5709	0.018*
C12	0.28787 (10)	0.74249 (7)	0.64720 (19)	0.0166 (2)
H12A	0.2822	0.7872	0.6989	0.020*
C13	0.38317 (10)	0.71327 (8)	0.64758 (19)	0.0180 (3)
H13A	0.4411	0.7386	0.6971	0.022*
C14	0.39122 (10)	0.64598 (8)	0.57341 (19)	0.0174 (2)
H14A	0.4547	0.6259	0.5753	0.021*
C15	0.30482 (10)	0.60840 (7)	0.49632 (18)	0.0145 (2)
H15A	0.3109	0.5633	0.4475	0.017*
C16	0.14644 (10)	0.28629 (7)	0.1275 (2)	0.0192 (3)
H16A	0.1515	0.2373	0.0953	0.029*
H16B	0.1769	0.2935	0.2574	0.029*
H16C	0.1809	0.3146	0.0467	0.029*
C17	−0.28331 (10)	0.43211 (8)	0.0262 (2)	0.0180 (3)
H17A	−0.3493	0.4533	0.0087	0.027*
H17B	−0.2835	0.3897	0.1001	0.027*
H17C	−0.2660	0.4207	−0.0952	0.027*
C18	0.37040 (11)	0.39561 (8)	0.7722 (2)	0.0242 (3)
H18B	0.3026	0.4161	0.7635	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.02401 (18)	0.02031 (17)	0.0454 (2)	−0.00121 (13)	0.01130 (16)	−0.00051 (15)
Cl2	0.0228 (2)	0.0362 (2)	0.0843 (4)	−0.00822 (17)	0.0141 (2)	−0.0291 (3)
Cl3	0.0574 (3)	0.0554 (3)	0.0515 (3)	−0.0064 (3)	−0.0090 (3)	0.0285 (3)
O1	0.0121 (4)	0.0099 (4)	0.0177 (4)	−0.0001 (3)	0.0017 (3)	−0.0016 (3)
O2	0.0126 (4)	0.0143 (4)	0.0299 (5)	0.0019 (3)	0.0021 (4)	−0.0024 (4)
O3	0.0171 (4)	0.0100 (4)	0.0271 (5)	0.0005 (3)	0.0050 (4)	−0.0030 (4)
O4	0.0113 (4)	0.0150 (4)	0.0211 (5)	−0.0005 (3)	0.0006 (3)	−0.0035 (3)
C1	0.0128 (5)	0.0108 (5)	0.0123 (5)	−0.0013 (4)	0.0026 (4)	0.0004 (4)
C2	0.0139 (5)	0.0112 (5)	0.0162 (5)	0.0009 (4)	0.0030 (4)	−0.0001 (4)
C3	0.0168 (6)	0.0100 (5)	0.0148 (5)	0.0002 (4)	0.0046 (4)	0.0004 (4)
C4	0.0151 (5)	0.0120 (5)	0.0148 (5)	−0.0023 (4)	0.0032 (4)	−0.0006 (4)
C5	0.0123 (5)	0.0134 (5)	0.0120 (5)	−0.0005 (4)	0.0025 (4)	0.0007 (4)
C6	0.0128 (5)	0.0105 (5)	0.0124 (5)	−0.0001 (4)	0.0025 (4)	0.0004 (4)
C7	0.0133 (5)	0.0118 (5)	0.0144 (5)	0.0000 (4)	0.0028 (4)	0.0005 (4)
C8	0.0141 (5)	0.0106 (5)	0.0167 (6)	0.0002 (4)	0.0020 (4)	−0.0011 (4)
C9	0.0141 (5)	0.0099 (5)	0.0122 (5)	−0.0006 (4)	0.0027 (4)	0.0002 (4)
C10	0.0131 (5)	0.0117 (5)	0.0117 (5)	−0.0011 (4)	0.0018 (4)	0.0005 (4)
C11	0.0155 (5)	0.0127 (5)	0.0162 (5)	−0.0001 (4)	0.0035 (4)	−0.0006 (4)
C12	0.0208 (6)	0.0132 (6)	0.0158 (6)	−0.0030 (5)	0.0031 (5)	−0.0021 (4)
C13	0.0168 (6)	0.0186 (6)	0.0177 (6)	−0.0053 (5)	0.0007 (5)	−0.0014 (5)
C14	0.0131 (5)	0.0199 (6)	0.0188 (6)	−0.0005 (5)	0.0015 (4)	−0.0009 (5)
C15	0.0143 (5)	0.0143 (6)	0.0147 (5)	0.0004 (4)	0.0015 (4)	−0.0008 (4)
C16	0.0178 (6)	0.0127 (6)	0.0280 (7)	0.0023 (5)	0.0059 (5)	0.0001 (5)
C17	0.0146 (6)	0.0199 (6)	0.0186 (6)	−0.0034 (5)	−0.0003 (4)	−0.0043 (5)
C18	0.0153 (6)	0.0204 (7)	0.0358 (8)	−0.0008 (5)	0.0013 (5)	−0.0001 (6)

Geometric parameters (Å, º)

Cl1—C18	1.7624 (16)	C8—H8A	0.93
Cl2—C18	1.7635 (17)	C9—C10	1.4730 (17)
Cl3—C18	1.7584 (18)	C10—C15	1.3994 (17)
O1—C9	1.3618 (15)	C10—C11	1.4030 (17)
O1—C1	1.3721 (15)	C11—C12	1.3880 (18)
O2—C7	1.2370 (16)	C11—H11A	0.93
O3—C3	1.3580 (15)	C12—C13	1.3912 (19)
O3—C16	1.4382 (16)	C12—H12A	0.93
O4—C5	1.3569 (15)	C13—C14	1.389 (2)
O4—C17	1.4316 (16)	C13—H13A	0.93
C1—C2	1.3924 (17)	C14—C15	1.3910 (18)
C1—C6	1.3998 (17)	C14—H14A	0.93
C2—C3	1.3834 (17)	C15—H15A	0.93
C2—H2A	0.93	C16—H16A	0.96
C3—C4	1.4059 (18)	C16—H16B	0.96
C4—C5	1.3826 (17)	C16—H16C	0.96
C4—H4A	0.93	C17—H17A	0.96
C5—C6	1.4279 (17)	C17—H17B	0.96
C6—C7	1.4665 (17)	C17—H17C	0.96
C7—C8	1.4514 (17)	C18—H18B	0.98
C8—C9	1.3471 (17)
C9—O1—C1	119.81 (10)	C12—C11—C10	120.16 (12)
C3—O3—C16	116.93 (11)	C12—C11—H11A	119.9
C5—O4—C17	117.09 (10)	C10—C11—H11A	119.9
O1—C1—C2	113.42 (11)	C11—C12—C13	120.58 (12)
O1—C1—C6	122.35 (11)	C11—C12—H12A	119.7
C2—C1—C6	124.23 (12)	C13—C12—H12A	119.7
C3—C2—C1	117.47 (12)	C14—C13—C12	119.53 (12)
C3—C2—H2A	121.3	C14—C13—H13A	120.2
C1—C2—H2A	121.3	C12—C13—H13A	120.2
O3—C3—C2	123.97 (12)	C13—C14—C15	120.40 (12)
O3—C3—C4	114.83 (11)	C13—C14—H14A	119.8
C2—C3—C4	121.19 (12)	C15—C14—H14A	119.8
C5—C4—C3	120.14 (12)	C14—C15—C10	120.33 (12)
C5—C4—H4A	119.9	C14—C15—H15A	119.8
C3—C4—H4A	119.9	C10—C15—H15A	119.8
O4—C5—C4	123.11 (11)	O3—C16—H16A	109.5
O4—C5—C6	116.12 (11)	O3—C16—H16B	109.5
C4—C5—C6	120.76 (11)	H16A—C16—H16B	109.5
C1—C6—C5	116.20 (11)	O3—C16—H16C	109.5
C1—C6—C7	118.78 (11)	H16A—C16—H16C	109.5
C5—C6—C7	125.00 (11)	H16B—C16—H16C	109.5
O2—C7—C8	120.22 (12)	O4—C17—H17A	109.5
O2—C7—C6	124.97 (12)	O4—C17—H17B	109.5
C8—C7—C6	114.81 (11)	H17A—C17—H17B	109.5
C9—C8—C7	122.54 (12)	O4—C17—H17C	109.5
C9—C8—H8A	118.7	H17A—C17—H17C	109.5
C7—C8—H8A	118.7	H17B—C17—H17C	109.5
C8—C9—O1	121.64 (11)	Cl3—C18—Cl1	109.41 (8)
C8—C9—C10	126.15 (12)	Cl3—C18—Cl2	109.88 (9)
O1—C9—C10	112.20 (10)	Cl1—C18—Cl2	110.45 (9)
C15—C10—C11	118.98 (12)	Cl3—C18—H18B	109.0
C15—C10—C9	120.62 (11)	Cl1—C18—H18B	109.0
C11—C10—C9	120.40 (11)	Cl2—C18—H18B	109.0
C9—O1—C1—C2	178.50 (11)	C1—C6—C7—O2	179.12 (13)
C9—O1—C1—C6	−1.80 (17)	C5—C6—C7—O2	0.9 (2)
O1—C1—C2—C3	179.32 (11)	C1—C6—C7—C8	−0.66 (17)
C6—C1—C2—C3	−0.37 (19)	C5—C6—C7—C8	−178.85 (12)
C16—O3—C3—C2	−4.50 (19)	O2—C7—C8—C9	178.46 (13)
C16—O3—C3—C4	176.10 (11)	C6—C7—C8—C9	−1.75 (18)
C1—C2—C3—O3	−179.14 (12)	C7—C8—C9—O1	2.52 (19)
C1—C2—C3—C4	0.23 (19)	C7—C8—C9—C10	−178.51 (12)
O3—C3—C4—C5	179.25 (11)	C1—O1—C9—C8	−0.72 (18)
C2—C3—C4—C5	−0.17 (19)	C1—O1—C9—C10	−179.82 (10)
C17—O4—C5—C4	−4.47 (18)	C8—C9—C10—C15	−170.69 (13)
C17—O4—C5—C6	175.83 (11)	O1—C9—C10—C15	8.37 (16)
C3—C4—C5—O4	−179.44 (12)	C8—C9—C10—C11	8.9 (2)
C3—C4—C5—C6	0.24 (19)	O1—C9—C10—C11	−172.05 (11)
O1—C1—C6—C5	−179.23 (11)	C15—C10—C11—C12	1.43 (19)
C2—C1—C6—C5	0.43 (18)	C9—C10—C11—C12	−178.16 (12)
O1—C1—C6—C7	2.43 (18)	C10—C11—C12—C13	−0.1 (2)
C2—C1—C6—C7	−177.91 (12)	C11—C12—C13—C14	−1.2 (2)
O4—C5—C6—C1	179.35 (11)	C12—C13—C14—C15	1.1 (2)
C4—C5—C6—C1	−0.36 (18)	C13—C14—C15—C10	0.3 (2)
O4—C5—C6—C7	−2.42 (18)	C11—C10—C15—C14	−1.56 (19)
C4—C5—C6—C7	177.87 (12)	C9—C10—C15—C14	178.03 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O1	0.93	2.37	2.7069 (16)	101
C18—H18B···O2^i	0.98	2.08	2.9240 (18)	143
C18—H18B···O4^i	0.98	2.51	3.3407 (18)	142
C12—H12A···Cg1^ii	0.93	2.73	3.3887 (14)	129
C17—H17B···Cg1^i	0.96	2.69	3.5547 (15)	151

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+3/2, z+1/2.