Dimethyl 2,2′-[(4-oxo-2-phenyl-4H-chromene-5,7-diyl)dioxy]diacetate: a more densely packed polymorph

Nallasivam, A.; Nethaji, M.; Vembu, N.; Jaswant, B.; Sulochana, N.

doi:10.1107/S1600536809001020

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages o312-o313

doi:10.1107/S1600536809001020

Open

access

Dimethyl 2,2′-[(4-oxo-2-phenyl-4H-chromene-5,7-diyl)dioxy]diacetate: a more densely packed polymorph

Angannan Nallasivam,^a Munirathinam Nethaji,^b Nagarajan Vembu,^c ^* Buckle Jaswant ^d and Nagarajan Sulochana ^a

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India, ^bDepartment of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560 012, India, ^cDepartment of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India, and ^dDepartment of Chemistry, Government Arts College, Karur 639 005, India
^*Correspondence e-mail: vembu57@yahoo.com

(Received 11 November 2008; accepted 8 January 2009; online 14 January 2009)

The title molecule, C₂₁H₁₈O₈, crystallizes in two crystal polymorphs, see also Nallasivam, Nethaji, Vembu & Jaswant [Acta Cryst. (2009), E65, o314–o315]. The molecules of both polymorphs differ by the conformation of the oxomethylacetate groups. The title molecules are rather planar compared to the molecules of the other polymorph. In the title molecule, one of the oxomethylacetate groups is disordered (occupancies of 0.6058/0.3942). The structures of both polymorphs are stabilized by C—H⋯O and C—H⋯π interactions. Due to the planarity of the title molecules and similar intermolecular interactions, the title molecules are more densely packed than those of the other polymorph.

Related literature

For a more detailed description of the two polymorphs, see: Nallasivam et al. (2009 ). For related structures, see: Wang, Fang et al. (2003 ); Wang, Zheng et al. (2003 ). For hydrogen bonding, see: Desiraju & Steiner (1999 ).

Experimental

Crystal data

C₂₁H₁₈O₈
M_r = 398.35
Triclinic, $[P \overline 1]$
a = 7.4290 (15) Å
b = 9.2582 (19) Å
c = 13.480 (3) Å
α = 84.232 (3)°
β = 88.775 (4)°
γ = 82.982 (3)°
V = 915.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 (2) K
0.34 × 0.28 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.963, T_max = 0.975
9755 measured reflections
3781 independent reflections
2887 reflections with I > 3σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.118
S = 2.47
3781 reflections
268 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O27ⁱ	0.93	2.38	3.304 (2)	169
C12—H12⋯O1	0.93	2.33	2.664 (2)	101
C15—H15⋯O21Bⁱⁱ	0.93	2.46	3.31 (6)	153
C25—H25B⋯O17ⁱⁱⁱ	0.97	2.56	3.447 (3)	153
C29—H29B⋯O17^iv	0.96	2.50	3.403 (3)	156
C29—H29C⋯O21B^iv	0.96	2.55	3.26 (6)	131
C23B—H23BB⋯Cg1^v	0.96	2.76	3.67 (6)	159 (6)
Symmetry codes: (i) -x, -y+3, -z+2; (ii) -x+1, -y+1, -z+2; (iii) x, y+1, z; (iv) x-1, y+1, z; (v) x, y, z-1. Cg1 is the centroid of the C11–C16 phenyl ring.

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: JANA2000 (Petříček et al., 2000 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and JANA2000.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001020/fb2129sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001020/fb2129Isup2.hkl

checkCIF report

Comment top

The importance of the benzopyrans and their derivatives is described in Nallasivam et al. (2009).

The chromene ring is almost planar and similar to that found in the related chromene derivatives (Wang, Zheng et al., 2003; Wang, Fang et al., 2003). The total puckering amplitude of the chromene ring is 0.040 (2)Å. The interplanar angle between the chromene ring and the 2-phenyl ring is 2.90 (6)° thereby indicating the almost coplanar arrangement (Fig. 1). The oxomethylacetate substituent at C7 is slightly distorted from coplanarity as discerned from the interplanar angle of 12.7 (1)°. Such a calculation for the oxomethylacetate group at C5 is not done due to disorder.

The crystal structure is stabilized by the interplay of C–H···O, C–H···π interactions (Tab. 1) as well as π···π-electron interactions. The H-bond distances agree with those reported in literature (Desiraju & Steiner, 1999). There is a π···π-electron interaction between the rings C5\C6···\C10 Cg2 and C11\C12···\C16 [1-x, 2-y, 2-z] whose centroids are at the distance 3.714 (1) Å.

Related literature top

For a more detailed description of the two polymorphs, see:Nallasivam et al. (2009). For related structures, see: Wang, Zheng et al. (2003); Wang, Fang et al. (2003). For hydrogen bonding, see: Desiraju & Steiner (1999). Cg1 is the centroid of the C11–C16 phenyl ring.

Experimental top

Into the round bottom flask a suspension of chrysin (3.93 mmol, 1 g) and potassium carbonate (11.81 mmol, 1.64 g) were deposited and to this mixture dimethylformamide (10 ml) was added. The reaction mixture was heated to 383 K and maintained at this temperature for 2–3 hrs. The reaction mixture was cooled to 353 K. Methyl chloroacetate (15.74 mmol, 1.70 g) was slowly added to the reaction mixture with the help of a dropping funnel. The reaction mixture was kept for 8–9 hrs at 353 K while the reaction was monitored by high pressure liquid chromatography. Once the reaction was completed, the reaction mixture was quenched with water and stirred for 30–45 min at 303 K. The obtained solid was filtered and washed with plenty of water followed by methanol. The wet cake was dried under vacuum at 343 K. The crude product of the title compound, i. e. the more densely packed polymorph, was dissolved in dichloromethane (10 ml) and mixed with equal amount of n-hexane. The clear solution was kept aside for a week without stirring. Diffraction quality prism shaped crystals with average size about 0.30 mm along the longest edge were obtained. The crystals were filtered and washed with n-hexane and dried under vacuum at 70°C. Yield: 85%

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: JANA2000 (Petříček et al., 2000); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and JANA2000 (Petříček et al., 2000).

Figures top

Fig. 1. The asymmetric unit of the title compound with the atoms labelled and displacement ellipsoids depicted at the 50% probability level for all non-H atoms. H-atoms are drawn as spheres of arbitrary radius.

Dimethyl 2,2'-[(4-oxo-2-phenyl-4H-chromene-5,7-diyl)dioxy]diacetate top

Crystal data top

C₂₁H₁₈O₈	Z = 2
M_r = 398.35	F(000) = 416
Triclinic, P1	D_x = 1.445 Mg m⁻³
Hall symbol: -P 1	Melting point = 411–414 K
a = 7.4290 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2582 (19) Å	Cell parameters from 574 reflections
c = 13.480 (3) Å	θ = 1.5–26.5°
α = 84.232 (3)°	µ = 0.11 mm⁻¹
β = 88.775 (4)°	T = 293 K
γ = 82.982 (3)°	Rectangular, colourless
V = 915.5 (3) Å³	0.34 × 0.28 × 0.22 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3781 independent reflections
Radiation source: fine-focus sealed tube	2887 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 0.3 pixels mm^-1	θ_max = 27.4°, θ_min = 1.5°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	k = −11→11
T_min = 0.963, T_max = 0.975	l = −17→17
9755 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)] = 0.059	Hydrogen site location: difference Fourier map
wR(F²) = 0.118	H-atom parameters constrained
S = 2.47	Weighting scheme based on measured s.u.'s w = 1/[σ²(I) + 0.0004I²]
3781 reflections	(Δ/σ)_max = 0.018
268 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³
73 constraints

Crystal data top

C₂₁H₁₈O₈	γ = 82.982 (3)°
M_r = 398.35	V = 915.5 (3) Å³
Triclinic, P1	Z = 2
a = 7.4290 (15) Å	Mo Kα radiation
b = 9.2582 (19) Å	µ = 0.11 mm⁻¹
c = 13.480 (3) Å	T = 293 K
α = 84.232 (3)°	0.34 × 0.28 × 0.22 mm
β = 88.775 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	3781 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	2887 reflections with I > 3σ(I)
T_min = 0.963, T_max = 0.975	R_int = 0.016
9755 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 2.47	Δρ_max = 0.40 e Å⁻³
3781 reflections	Δρ_min = −0.26 e Å⁻³
268 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.30663 (16)	0.96130 (13)	1.06056 (8)	0.0466 (4)
C2	0.3857 (2)	0.82585 (19)	1.09503 (13)	0.0431 (6)
C3	0.4037 (2)	0.7161 (2)	1.03579 (13)	0.0481 (7)
H3	0.462382	0.628089	1.064955	0.0577*
C4	0.3379 (2)	0.73194 (19)	0.93493 (13)	0.0447 (6)
C5	0.1751 (2)	0.92338 (19)	0.80498 (13)	0.0440 (6)
C6	0.0924 (2)	1.06310 (19)	0.78160 (13)	0.0485 (7)
H6	0.040296	1.087598	0.71911	0.0582*
C7	0.0866 (2)	1.16664 (19)	0.85047 (13)	0.0431 (6)
C8	0.1604 (2)	1.13114 (18)	0.94310 (12)	0.0425 (6)
H8	0.156976	1.200597	0.988599	0.051*
C9	0.2523 (2)	0.87883 (19)	0.90045 (12)	0.0412 (6)
C10	0.2396 (2)	0.98822 (19)	0.96535 (12)	0.0404 (6)
C11	0.4412 (2)	0.82212 (19)	1.19964 (13)	0.0442 (6)
C12	0.4040 (3)	0.9455 (2)	1.25078 (13)	0.0566 (7)
H12	0.343711	1.031075	1.2191	0.0679*
C13	0.4559 (3)	0.9425 (2)	1.34867 (14)	0.0662 (9)
H13	0.430455	1.025051	1.382886	0.0795*
C14	0.5450 (3)	0.8187 (2)	1.39655 (15)	0.0682 (9)
H14	0.579756	0.818894	1.462394	0.0818*
C15	0.5827 (3)	0.6948 (2)	1.34736 (14)	0.0639 (8)
H15	0.64295	0.610021	1.380221	0.0767*
C16	0.5311 (3)	0.6965 (2)	1.24944 (14)	0.0540 (7)
H16	0.557134	0.612394	1.216813	0.0648*
O17	0.3521 (2)	0.62674 (13)	0.88447 (9)	0.0631 (5)
O24	0.00341 (17)	1.30050 (13)	0.81551 (9)	0.0543 (5)
C25	0.0005 (3)	1.41742 (19)	0.87637 (13)	0.0510 (7)
H25a	−0.042676	1.386777	0.942667	0.0612*
H25b	0.122418	1.44296	0.881842	0.0612*
C26	−0.1214 (3)	1.5488 (2)	0.83259 (14)	0.0515 (7)
O27	−0.1465 (2)	1.65854 (16)	0.87223 (11)	0.0857 (7)
O28	−0.19680 (19)	1.52877 (14)	0.74809 (10)	0.0629 (5)
C29	−0.3222 (3)	1.6483 (2)	0.70402 (17)	0.0749 (9)
H29a	−0.258565	1.731194	0.685106	0.1124*
H29b	−0.415753	1.673972	0.751552	0.1124*
H29c	−0.375575	1.619165	0.646084	0.1124*
O18a	0.1645 (15)	0.8187 (11)	0.7443 (6)	0.0454 (13)	0.3942
C19a	0.1208 (13)	0.8711 (7)	0.6431 (7)	0.0539 (9)	0.3942
H19aa	0.208107	0.93525	0.616762	0.0647*	0.3942
H19ba	−0.002303	0.920137	0.640124	0.0647*	0.3942
C20a	0.1342 (9)	0.7395 (6)	0.5854 (5)	0.0499 (10)	0.3942
O21a	0.2023 (7)	0.6206 (5)	0.6126 (4)	0.0810 (12)	0.3942
O22a	0.0619 (16)	0.7758 (10)	0.4972 (6)	0.0728 (8)	0.3942
C23a	0.0795 (19)	0.6627 (13)	0.4291 (6)	0.0683 (15)	0.3942
H23aa	−0.019173	0.680175	0.38296	0.1025*	0.3942
H23ba	0.192314	0.664225	0.393153	0.1025*	0.3942
H23ca	0.077136	0.568838	0.466291	0.1025*	0.3942
O18b	0.209 (9)	0.823 (7)	0.734 (4)	0.0454 (12)	0.6058
C19b	0.108 (9)	0.860 (7)	0.643 (4)	0.0539 (9)	0.6058
H19ab	0.136	0.955	0.613	0.0647*	0.6058
H19bb	−0.020	0.861	0.658	0.0647*	0.6058
C20b	0.169 (9)	0.745 (7)	0.575 (4)	0.0499 (10)	0.6058
O21b	0.298 (9)	0.657 (7)	0.585 (4)	0.0810 (13)	0.6058
O22b	0.058 (9)	0.756 (7)	0.500 (4)	0.0728 (9)	0.6058
C23b	0.109 (9)	0.660 (7)	0.422 (4)	0.0683 (14)	0.6058
H23ab	0.002	0.641	0.390	0.1025*	0.6058
H23bb	0.188	0.705	0.375	0.1025*	0.6058
H23cb	0.171	0.569	0.452	0.1025*	0.6058

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0634 (8)	0.0405 (7)	0.0362 (7)	−0.0007 (6)	−0.0085 (6)	−0.0092 (5)
C2	0.0488 (11)	0.0395 (10)	0.0406 (10)	−0.0030 (8)	−0.0026 (8)	−0.0041 (8)
C3	0.0613 (12)	0.0393 (11)	0.0422 (11)	0.0007 (9)	−0.0052 (9)	−0.0034 (9)
C4	0.0550 (12)	0.0397 (10)	0.0407 (10)	−0.0067 (9)	−0.0008 (9)	−0.0092 (8)
C5	0.0542 (11)	0.0415 (11)	0.0382 (10)	−0.0048 (9)	−0.0028 (9)	−0.0141 (8)
C6	0.0610 (12)	0.0460 (11)	0.0389 (10)	0.0007 (9)	−0.0115 (9)	−0.0126 (9)
C7	0.0493 (11)	0.0387 (10)	0.0415 (11)	0.0004 (8)	−0.0071 (8)	−0.0101 (8)
C8	0.0508 (11)	0.0382 (10)	0.0405 (10)	−0.0035 (8)	−0.0024 (9)	−0.0150 (8)
C9	0.0488 (11)	0.0389 (10)	0.0369 (10)	−0.0053 (8)	−0.0006 (8)	−0.0084 (8)
C10	0.0463 (11)	0.0428 (10)	0.0330 (10)	−0.0058 (8)	−0.0043 (8)	−0.0070 (8)
C11	0.0501 (11)	0.0446 (11)	0.0387 (10)	−0.0061 (9)	−0.0041 (8)	−0.0063 (8)
C12	0.0733 (14)	0.0501 (12)	0.0450 (12)	0.0026 (10)	−0.0118 (10)	−0.0074 (9)
C13	0.0943 (17)	0.0586 (14)	0.0456 (12)	0.0007 (12)	−0.0151 (12)	−0.0133 (10)
C14	0.0906 (16)	0.0720 (15)	0.0415 (12)	−0.0047 (13)	−0.0191 (11)	−0.0061 (11)
C15	0.0808 (15)	0.0557 (13)	0.0513 (13)	0.0012 (11)	−0.0194 (11)	0.0061 (11)
C16	0.0660 (13)	0.0469 (12)	0.0483 (12)	−0.0028 (10)	−0.0051 (10)	−0.0050 (9)
O17	0.0964 (11)	0.0410 (8)	0.0521 (8)	0.0037 (7)	−0.0148 (8)	−0.0163 (7)
O24	0.0758 (9)	0.0410 (7)	0.0454 (8)	0.0097 (7)	−0.0183 (7)	−0.0176 (6)
C25	0.0640 (13)	0.0451 (11)	0.0462 (11)	−0.0016 (9)	−0.0113 (9)	−0.0188 (9)
C26	0.0646 (13)	0.0428 (11)	0.0482 (11)	−0.0004 (9)	−0.0069 (10)	−0.0169 (9)
O27	0.1173 (13)	0.0557 (9)	0.0844 (11)	0.0210 (9)	−0.0296 (10)	−0.0403 (9)
O28	0.0860 (10)	0.0460 (8)	0.0543 (8)	0.0130 (7)	−0.0227 (7)	−0.0150 (7)
C29	0.0941 (18)	0.0538 (13)	0.0706 (15)	0.0179 (12)	−0.0208 (13)	−0.0041 (11)
O18a	0.064 (4)	0.0384 (9)	0.0340 (10)	−0.0010 (16)	−0.0036 (17)	−0.0123 (6)
C19a	0.0779 (19)	0.0424 (12)	0.0428 (11)	−0.0047 (12)	−0.0164 (12)	−0.0109 (10)
C20a	0.067 (2)	0.0432 (13)	0.0399 (13)	−0.0034 (13)	−0.0088 (14)	−0.0072 (10)
O21a	0.126 (3)	0.0534 (12)	0.0584 (17)	0.025 (2)	−0.026 (2)	−0.0159 (11)
O22a	0.1281 (17)	0.0475 (14)	0.0427 (8)	0.0023 (14)	−0.0274 (10)	−0.0139 (8)
C23a	0.104 (4)	0.0602 (17)	0.0447 (13)	−0.0086 (18)	−0.0085 (16)	−0.0243 (12)
O18b	0.054 (3)	0.0478 (18)	0.0344 (12)	0.0054 (17)	−0.0039 (15)	−0.0159 (11)
C19b	0.0620 (16)	0.0513 (16)	0.0491 (12)	0.0063 (11)	−0.0157 (11)	−0.0211 (11)
C20b	0.0555 (19)	0.0502 (17)	0.0436 (14)	0.0037 (13)	−0.0099 (13)	−0.0131 (12)
O21b	0.074 (3)	0.097 (2)	0.0673 (19)	0.0350 (17)	−0.0209 (19)	−0.0378 (15)
O22b	0.0888 (16)	0.0733 (18)	0.0544 (9)	0.0260 (12)	−0.0302 (9)	−0.0340 (9)
C23b	0.091 (3)	0.070 (2)	0.0462 (15)	0.0046 (19)	−0.0098 (15)	−0.0298 (14)

Geometric parameters (Å, º) top

O1—C2	1.359 (2)	C25—H25a	0.9700
O1—C10	1.375 (2)	C25—H25b	0.970
C2—C3	1.347 (3)	C25—C26	1.502 (2)
C2—C11	1.474 (2)	C26—O27	1.188 (3)
C3—H3	0.9300	C26—O28	1.319 (2)
C3—C4	1.442 (2)	O28—C29	1.444 (2)
C4—C9	1.464 (2)	C29—H29a	0.960
C4—O17	1.236 (2)	C29—H29b	0.960
C5—C6	1.372 (2)	C29—H29c	0.960
C5—C9	1.422 (2)	O18a—C19a	1.431 (13)
C5—O18a	1.340 (10)	C19a—H19aa	0.970
C5—O18b	1.40 (6)	C19a—H19ba	0.970
C6—H6	0.9300	C19a—C20a	1.503 (10)
C6—C7	1.396 (3)	C19a—H19ab	0.86
C7—C8	1.368 (2)	H19ba—C19b	0.93
C7—O24	1.3593 (19)	C20a—O21a	1.181 (7)
C8—H8	0.9300	C20a—O22a	1.310 (11)
C8—C10	1.387 (2)	O22a—C23a	1.453 (15)
C9—C10	1.397 (3)	C23a—H23aa	0.960
C11—C12	1.389 (3)	C23a—H23ba	0.960
C11—C16	1.387 (2)	C23a—H23ca	0.960
C12—H12	0.9300	O18b—C19b	1.43 (8)
C12—C13	1.379 (3)	C19b—H19ab	0.97
C13—H13	0.930	C19b—H19bb	0.97
C13—C14	1.360 (3)	C19b—C20b	1.50 (9)
C14—H14	0.930	C20b—O21b	1.18 (9)
C14—C15	1.379 (3)	C20b—O22b	1.31 (8)
C15—H15	0.930	O22b—C23b	1.45 (9)
C15—C16	1.380 (3)	C23b—H23ab	0.96
C16—H16	0.930	C23b—H23bb	0.96
O24—C25	1.420 (2)	C23b—H23cb	0.96

C2—O1—C10	120.73 (14)	H25a—C25—H25b	108.35
O1—C2—C3	120.63 (15)	H25a—C25—C26	109.47
O1—C2—C11	110.99 (15)	H25b—C25—C26	109.47
C3—C2—C11	128.38 (15)	C25—C26—O27	122.01 (18)
C2—C3—H3	114.72	C25—C26—O28	113.56 (16)
C2—C3—C4	123.30 (15)	O27—C26—O28	124.42 (17)
H3—C3—C4	121.98	C26—O28—C29	116.61 (15)
C3—C4—C9	114.63 (16)	O28—C29—H29a	109.5
C3—C4—O17	120.99 (15)	O28—C29—H29b	109.47
C9—C4—O17	124.36 (16)	O28—C29—H29c	109.47
C6—C5—C9	121.19 (17)	H29a—C29—H29b	109.5
C6—C5—O18a	121.2 (4)	H29a—C29—H29c	109.5
C6—C5—O18b	122 (2)	H29b—C29—H29c	109.5
C9—C5—O18a	117.0 (4)	C5—O18a—C19a	114.8 (7)
C9—C5—O18b	116 (2)	C5—O18a—C19b	119 (3)
C5—C6—H6	118.85	O18a—C19a—H19aa	109.5
C5—C6—C7	120.54 (16)	O18a—C19a—H19ba	109.5
H6—C6—C7	120.61	O18a—C19a—C20a	106.9 (6)
C6—C7—C8	121.07 (15)	O18a—C19a—C20b	109 (2)
C6—C7—O24	113.49 (14)	H19aa—C19a—H19ba	112.0 (6)
C8—C7—O24	125.43 (16)	H19aa—C19a—C20a	109.5 (8)
C7—C8—H8	120.81	H19ba—C19a—C20a	109.5 (8)
C7—C8—C10	117.06 (16)	C19a—C20a—O21a	126.3 (7)
H8—C8—C10	122.13	C19a—C20a—O22a	110.0 (6)
C4—C9—C5	126.02 (16)	O21a—C20a—O22a	123.7 (7)
C4—C9—C10	119.19 (15)	C20a—O22a—C23a	116.3 (8)
C5—C9—C10	114.79 (15)	O22a—C23a—H23aa	109.5
O1—C10—C8	113.17 (15)	O22a—C23a—H23ba	109.5
O1—C10—C9	121.50 (14)	O22a—C23a—H23ca	109.5
C8—C10—C9	125.33 (15)	H23aa—C23a—H23ba	109.5
C2—C11—C12	120.37 (15)	H23aa—C23a—H23ca	109.5
C2—C11—C16	121.24 (16)	H23ba—C23a—H23ca	109.5
C12—C11—C16	118.39 (16)	C5—O18b—C19a	113 (4)
C11—C12—H12	120.07	C5—O18b—C19b	115 (5)
C11—C12—C13	120.55 (17)	C5—O18b—C19b	115 (5)
H12—C12—C13	119.4	O18b—C19b—H19ab	109
C12—C13—H13	120.44	O18b—C19b—H19bb	109
C12—C13—C14	120.5 (2)	O18b—C19b—C20b	107
H13—C13—C14	119.07	H19ab—C19b—H19bb	112
C13—C14—H14	119.3	H19ab—C19b—C20b	109
C13—C14—C15	119.95 (19)	H19bb—C19b—C20b	109
H14—C14—C15	120.7	C19b—C20b—O21b	126 (6)
C14—C15—H15	119.9	C19b—C20b—O22b	110 (6)
C14—C15—C16	120.03 (18)	O21b—C20b—O22b	124 (6)
H15—C15—C16	120.0	C20b—O22b—C23b	116 (6)
C11—C16—C15	120.57 (18)	O22b—C23b—H23ab	109
C11—C16—H16	119.94	O22b—C23b—H23bb	109
C15—C16—H16	119.49	O22b—C23b—H23cb	109
C7—O24—C25	118.58 (13)	H23ab—C23b—H23bb	109
O24—C25—H25a	109.47	H23ab—C23b—H23cb	109
O24—C25—H25b	109.47	H23bb—C23b—H23cb	109
O24—C25—C26	110.57 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O27ⁱ	0.93	2.38	3.304 (2)	169
C12—H12···O1	0.93	2.33	2.664 (2)	101
C15—H15···O21Bⁱⁱ	0.93	2.46	3.31 (6)	153
C25—H25B···O17ⁱⁱⁱ	0.97	2.56	3.447 (3)	153
C29—H29B···O17^iv	0.96	2.50	3.403 (3)	156
C29—H29C···O21B^iv	0.96	2.55	3.26 (6)	131
C23B—H23BB···Cg1^v	0.96	2.76	3.67 (6)	159 (6)

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈O₈
M_r	398.35
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.4290 (15), 9.2582 (19), 13.480 (3)
α, β, γ (°)	84.232 (3), 88.775 (4), 82.982 (3)
V (Å³)	915.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.34 × 0.28 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.963, 0.975
No. of measured, independent and observed [I > 3σ(I)] reflections	9755, 3781, 2887
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.118, 2.47
No. of reflections	3781
No. of parameters	268
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.26

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), PLATON (Spek, 2003), SHELXL97 (Sheldrick, 2008) and JANA2000 (Petříček et al., 2000).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O27ⁱ	0.93	2.38	3.304 (2)	169
C12—H12···O1	0.93	2.33	2.664 (2)	101
C15—H15···O21Bⁱⁱ	0.93	2.46	3.31 (6)	153
C25—H25B···O17ⁱⁱⁱ	0.97	2.56	3.447 (3)	153
C29—H29B···O17^iv	0.96	2.50	3.403 (3)	156
C29—H29C···O21B^iv	0.96	2.55	3.26 (6)	131
C23B—H23BB···Cg1^v	0.96	2.76	3.67 (6)	159 (6)

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

Acknowledgements

AN thanks Dr Naresh Kumar and Dr G. Vengatachalam, School of Chemistry, Bharathidasan University, Tiruchirappalli, and Organica Aromatics Pvt Ltd, Bangalore, India, for providing laboratory facilities.

References

Bruker (1999). SMART and SAINT. Bruker AXS Inc, Madison, Wisconsin, USA. Google Scholar
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press. Google Scholar
Nallasivam, A., Nethaji, M., Vembu, N., Jaswant, B. & Sulochana, N. (2009). Acta Cryst. E65, o314–o315. Web of Science CSD CrossRef IUCr Journals Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2000). JANA2000. Institute of Physics, Czech Academy of Science, Czech Republic. Google Scholar
Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, J.-F., Fang, M.-J., Huang, H.-Q., Li, G.-L., Su, W.-J. & Zhao, Y.-F. (2003). Acta Cryst. E59, o1517–o1518. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, J.-F., Zhang, Y.-J., Fang, M.-J., Huang, Y.-J., Wei, Z.-B., Zheng, Z.-H., Su, W.-J. & Zhao, Y.-F. (2003). Acta Cryst. E59, o1244–o1245. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 2| February 2009| Pages o312-o313

doi:10.1107/S1600536809001020

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Di­methyl 2,2′-[(4-oxo-2-phenyl-4H-chromene-5,7-diyl)di­oxy]di­acetate: a more densely packed polymorph

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Dimethyl 2,2′-[(4-oxo-2-phenyl-4H-chromene-5,7-diyl)dioxy]diacetate: a more densely packed polymorph