A second ortho-rhom-bic polymorph of (Z)-3-(9-anthr-yl)-1-(2-thien-yl)prop-2-en-1-one.

The title heteroaryl chalcone, C(21)H(14)OS, is a second ortho-rhom-bic polymorph which crystallizes in the space group P2(1)2(1)2(1). The structure was previously reported [Fun et al. (2009 ▶). Acta Cryst. E65, o2168-o2169] in the space group Pna2(1). The bond distances and angles are similar in both structures. In contrast, the overall crystal packing is different from that in the first ortho-rhom-bic Pna2(1) polymorph in which mol-ecules were stacked into columns along the b axis and the thio-phene units of two adjacent columns were stacked in a head to tail fashion. In the present polymorph, mol-ecules are found to dimerize through a weak S⋯S inter-action [3.6513 (7) Å] and these dimers are arranged into sheets parallel to the bc plane. There are no classical hydrogen bonds in the packing which features short C⋯O [3.2832 (2)-3.6251 (9) Å], C⋯S [3.4879 (17)-3.6251 (19) Å] and S⋯O [2.9948 (16) Å] contacts, together with C-H⋯π inter-actions. Similar contacts were found in the other polymorph.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For the structure of the first polymorph, see: Fun et al. (2009 ▶). For background to and applications of chalcones, see: Chantrapromma et al. (2009 ▶); Patil & Dharmaprakash (2008 ▶); Saydam et al. (2003 ▶); Suwunwong et al. (2009 ▶); Svetlichny et al. (2007 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C21H14OS

M = 314.38

Orthorhombic,

a = 5.5116 (1) Å

b = 14.8497 (2) Å

c = 18.3625 (3) Å

V = 1502.89 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 100 K

0.50 × 0.19 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.900, T max = 0.977

14062 measured reflections

4354 independent reflections

4035 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.108

S = 1.05

4354 reflections

254 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.79 e Å−3

Δρmin = −0.62 e Å−3

Absolute structure: Flack (1983 ▶), 1830 Friedel pairs

Flack parameter: 0.04 (8)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000061/sj2716sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000061/sj2716Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H14OS	Dx = 1.390 Mg m−3
Mr = 314.38	Melting point = 400–401 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4354 reflections
a = 5.5116 (1) Å	θ = 1.8–30.0°
b = 14.8497 (2) Å	µ = 0.22 mm−1
c = 18.3625 (3) Å	T = 100 K
V = 1502.89 (4) Å3	Block, yellow
Z = 4	0.50 × 0.19 × 0.11 mm
F(000) = 656

Bruker APEXII CCD area-detector diffractometer	4354 independent reflections
Radiation source: sealed tube	4035 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 30.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→5
Tmin = 0.900, Tmax = 0.977	k = −17→20
14062 measured reflections	l = −25→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.8977P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
4354 reflections	Δρmax = 0.79 e Å−3
254 parameters	Δρmin = −0.62 e Å−3
0 restraints	Absolute structure: Flack (1983), 1830 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.04 (8)

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
S1	0.79023 (9)	0.82740 (3)	0.98167 (3)	0.01920 (11)
O1	0.6379 (3)	0.74101 (10)	0.84157 (8)	0.0208 (3)
C1	0.6215 (3)	0.62511 (12)	0.66251 (10)	0.0142 (3)
C2	0.6199 (4)	0.69201 (13)	0.60656 (10)	0.0176 (4)
H2A	0.747 (4)	0.7404 (15)	0.6071 (12)	0.019 (6)*
C3	0.4549 (4)	0.68828 (13)	0.55096 (10)	0.0193 (4)
H3A	0.459 (4)	0.7304 (16)	0.5132 (14)	0.022 (6)*
C4	0.2761 (4)	0.61930 (13)	0.54827 (11)	0.0198 (4)
H4A	0.150 (5)	0.6169 (17)	0.5090 (13)	0.026 (6)*
C5	0.2685 (4)	0.55527 (13)	0.60124 (10)	0.0184 (4)
H5A	0.155 (5)	0.5111 (18)	0.6021 (14)	0.033 (7)*
C6	0.4394 (3)	0.55565 (12)	0.65992 (10)	0.0146 (3)
C7	0.4332 (4)	0.49043 (12)	0.71450 (10)	0.0169 (4)
H7A	0.311 (4)	0.4456 (14)	0.7129 (11)	0.010 (5)*
C8	0.6064 (4)	0.48855 (12)	0.76949 (10)	0.0159 (4)
C9	0.6059 (4)	0.41897 (13)	0.82390 (11)	0.0213 (4)
H9A	0.479 (4)	0.3744 (16)	0.8218 (13)	0.019 (6)*
C10	0.7811 (4)	0.41528 (14)	0.87607 (11)	0.0240 (4)
H10A	0.788 (5)	0.3656 (16)	0.9099 (13)	0.022 (6)*
C11	0.9682 (4)	0.48106 (15)	0.87753 (11)	0.0222 (4)
H11A	1.103 (5)	0.4744 (16)	0.9123 (13)	0.023 (6)*
C12	0.9731 (4)	0.54951 (14)	0.82813 (10)	0.0189 (4)
H12A	1.091 (5)	0.5966 (17)	0.8299 (13)	0.027 (7)*
C13	0.7917 (4)	0.55659 (12)	0.77254 (9)	0.0156 (3)
C14	0.7917 (3)	0.62627 (12)	0.72009 (9)	0.0143 (3)
C15	0.9746 (4)	0.69969 (13)	0.72208 (10)	0.0172 (4)
H15A	1.077 (4)	0.7024 (15)	0.6807 (12)	0.016 (6)*
C16	1.0028 (4)	0.76158 (13)	0.77411 (10)	0.0178 (4)
H16A	1.138 (5)	0.8035 (17)	0.7711 (13)	0.026 (6)*
C17	0.8452 (3)	0.77098 (12)	0.83955 (10)	0.0153 (3)
C18	0.9491 (3)	0.82083 (12)	0.90132 (9)	0.0146 (3)
C19	1.1727 (3)	0.86783 (12)	0.90518 (10)	0.0146 (2)
H19A	1.2863	0.8714	0.8678	0.018*
C20	1.1971 (3)	0.90888 (11)	0.97520 (10)	0.0146 (2)
H20A	1.351 (5)	0.9445 (17)	0.9876 (14)	0.031 (7)*
C21	1.0083 (4)	0.89174 (13)	1.02086 (11)	0.0198 (4)
H21A	0.993 (5)	0.9095 (18)	1.0753 (15)	0.034 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0185 (2)	0.0204 (2)	0.0188 (2)	−0.00094 (17)	0.00214 (18)	−0.00059 (18)
O1	0.0163 (6)	0.0219 (7)	0.0243 (7)	−0.0038 (6)	0.0037 (6)	−0.0053 (6)
C1	0.0159 (8)	0.0132 (8)	0.0136 (8)	0.0006 (7)	0.0018 (6)	−0.0028 (6)
C2	0.0200 (9)	0.0167 (8)	0.0162 (8)	0.0000 (7)	0.0013 (7)	−0.0014 (7)
C3	0.0234 (9)	0.0181 (9)	0.0163 (8)	0.0033 (7)	−0.0002 (7)	0.0009 (7)
C4	0.0211 (9)	0.0210 (9)	0.0174 (8)	0.0038 (8)	−0.0038 (8)	−0.0049 (7)
C5	0.0182 (9)	0.0167 (8)	0.0204 (8)	0.0001 (7)	−0.0007 (8)	−0.0057 (7)
C6	0.0140 (8)	0.0143 (8)	0.0155 (8)	0.0007 (7)	−0.0001 (7)	−0.0056 (7)
C7	0.0187 (9)	0.0131 (8)	0.0188 (8)	−0.0010 (7)	0.0030 (7)	−0.0038 (7)
C8	0.0192 (9)	0.0142 (8)	0.0143 (8)	0.0023 (7)	0.0050 (7)	−0.0007 (7)
C9	0.0279 (11)	0.0152 (9)	0.0208 (9)	0.0012 (8)	0.0065 (8)	0.0002 (7)
C10	0.0325 (11)	0.0215 (9)	0.0179 (8)	0.0078 (9)	0.0061 (9)	0.0032 (7)
C11	0.0254 (10)	0.0262 (10)	0.0149 (8)	0.0088 (9)	0.0012 (8)	0.0007 (8)
C12	0.0182 (9)	0.0219 (9)	0.0166 (8)	0.0029 (8)	0.0016 (7)	−0.0013 (7)
C13	0.0164 (8)	0.0170 (8)	0.0133 (7)	0.0038 (7)	0.0036 (7)	−0.0019 (6)
C14	0.0146 (7)	0.0144 (8)	0.0141 (7)	0.0014 (7)	0.0019 (7)	−0.0028 (6)
C15	0.0163 (8)	0.0213 (9)	0.0141 (8)	−0.0014 (7)	0.0026 (7)	0.0002 (7)
C16	0.0170 (9)	0.0198 (9)	0.0165 (8)	−0.0033 (7)	0.0013 (7)	0.0000 (7)
C17	0.0173 (9)	0.0118 (8)	0.0167 (8)	−0.0001 (7)	0.0011 (7)	−0.0010 (6)
C18	0.0161 (8)	0.0151 (8)	0.0125 (7)	0.0021 (7)	0.0022 (6)	0.0003 (7)
C19	0.0125 (5)	0.0149 (5)	0.0164 (6)	0.0005 (5)	−0.0024 (5)	−0.0019 (5)
C20	0.0125 (5)	0.0149 (5)	0.0164 (6)	0.0005 (5)	−0.0024 (5)	−0.0019 (5)
C21	0.0243 (9)	0.0190 (8)	0.0161 (8)	0.0040 (7)	−0.0012 (8)	−0.0017 (7)

S1—C21	1.696 (2)	C9—H9A	0.96 (3)
S1—C18	1.7184 (18)	C10—C11	1.421 (3)
O1—C17	1.227 (2)	C10—H10A	0.97 (2)
C1—C14	1.414 (3)	C11—C12	1.363 (3)
C1—C2	1.429 (3)	C11—H11A	0.98 (3)
C1—C6	1.440 (3)	C12—C13	1.433 (3)
C2—C3	1.368 (3)	C12—H12A	0.96 (3)
C2—H2A	1.00 (2)	C13—C14	1.414 (2)
C3—C4	1.422 (3)	C14—C15	1.485 (3)
C3—H3A	0.93 (2)	C15—C16	1.335 (3)
C4—C5	1.361 (3)	C15—H15A	0.95 (2)
C4—H4A	1.00 (3)	C16—C17	1.489 (3)
C5—C6	1.431 (3)	C16—H16A	0.97 (3)
C5—H5A	0.91 (3)	C17—C18	1.470 (3)
C6—C7	1.394 (3)	C18—C19	1.418 (3)
C7—C8	1.390 (3)	C19—C20	1.429 (2)
C7—H7A	0.95 (2)	C19—H19A	0.9300
C8—C9	1.437 (3)	C20—C21	1.360 (3)
C8—C13	1.438 (3)	C20—H20A	1.02 (3)
C9—C10	1.361 (3)	C21—H21A	1.04 (3)
C21—S1—C18	92.02 (10)	C12—C11—H11A	119.5 (15)
C14—C1—C2	122.21 (17)	C10—C11—H11A	119.4 (14)
C14—C1—C6	119.73 (17)	C11—C12—C13	121.0 (2)
C2—C1—C6	118.05 (17)	C11—C12—H12A	122.4 (16)
C3—C2—C1	120.81 (18)	C13—C12—H12A	116.5 (16)
C3—C2—H2A	120.0 (13)	C14—C13—C12	122.62 (18)
C1—C2—H2A	119.1 (13)	C14—C13—C8	119.20 (17)
C2—C3—C4	121.04 (18)	C12—C13—C8	118.16 (17)
C2—C3—H3A	120.8 (15)	C13—C14—C1	120.04 (17)
C4—C3—H3A	118.2 (15)	C13—C14—C15	121.37 (16)
C5—C4—C3	119.99 (18)	C1—C14—C15	118.55 (16)
C5—C4—H4A	118.0 (15)	C16—C15—C14	127.01 (17)
C3—C4—H4A	122.0 (15)	C16—C15—H15A	118.3 (14)
C4—C5—C6	120.99 (19)	C14—C15—H15A	114.7 (14)
C4—C5—H5A	122.6 (17)	C15—C16—C17	125.05 (17)
C6—C5—H5A	116.4 (17)	C15—C16—H16A	119.3 (15)
C7—C6—C5	121.47 (17)	C17—C16—H16A	115.6 (15)
C7—C6—C1	119.43 (17)	O1—C17—C18	121.46 (17)
C5—C6—C1	119.10 (17)	O1—C17—C16	122.25 (17)
C8—C7—C6	121.27 (17)	C18—C17—C16	116.26 (16)
C8—C7—H7A	119.8 (13)	C19—C18—C17	128.65 (16)
C6—C7—H7A	118.9 (13)	C19—C18—S1	111.83 (13)
C7—C8—C9	121.21 (18)	C17—C18—S1	119.51 (14)
C7—C8—C13	120.14 (17)	C18—C19—C20	109.67 (16)
C9—C8—C13	118.65 (18)	C18—C19—H19A	125.2
C10—C9—C8	121.1 (2)	C20—C19—H19A	125.2
C10—C9—H9A	121.0 (14)	C21—C20—C19	113.75 (16)
C8—C9—H9A	117.8 (14)	C21—C20—H20A	126.4 (15)
C9—C10—C11	120.04 (18)	C19—C20—H20A	119.8 (15)
C9—C10—H10A	120.8 (16)	C20—C21—S1	112.71 (15)
C11—C10—H10A	119.0 (16)	C20—C21—H21A	127.5 (16)
C12—C11—C10	121.0 (2)	S1—C21—H21A	119.7 (16)
C14—C1—C2—C3	179.06 (17)	C9—C8—C13—C12	2.5 (3)
C6—C1—C2—C3	−2.1 (3)	C12—C13—C14—C1	174.11 (17)
C1—C2—C3—C4	1.7 (3)	C8—C13—C14—C1	−4.4 (3)
C2—C3—C4—C5	−0.5 (3)	C12—C13—C14—C15	−3.3 (3)
C3—C4—C5—C6	−0.4 (3)	C8—C13—C14—C15	178.18 (16)
C4—C5—C6—C7	179.95 (18)	C2—C1—C14—C13	−177.53 (17)
C4—C5—C6—C1	0.0 (3)	C6—C1—C14—C13	3.6 (3)
C14—C1—C6—C7	0.2 (3)	C2—C1—C14—C15	0.0 (3)
C2—C1—C6—C7	−178.75 (17)	C6—C1—C14—C15	−178.90 (16)
C14—C1—C6—C5	−179.92 (16)	C13—C14—C15—C16	−64.2 (3)
C2—C1—C6—C5	1.2 (3)	C1—C14—C15—C16	118.4 (2)
C5—C6—C7—C8	176.94 (17)	C14—C15—C16—C17	−2.9 (3)
C1—C6—C7—C8	−3.1 (3)	C15—C16—C17—O1	−21.8 (3)
C6—C7—C8—C9	−177.26 (17)	C15—C16—C17—C18	160.02 (19)
C6—C7—C8—C13	2.3 (3)	O1—C17—C18—C19	−172.54 (18)
C7—C8—C9—C10	177.47 (19)	C16—C17—C18—C19	5.7 (3)
C13—C8—C9—C10	−2.1 (3)	O1—C17—C18—S1	6.9 (2)
C8—C9—C10—C11	0.2 (3)	C16—C17—C18—S1	−174.86 (13)
C9—C10—C11—C12	1.3 (3)	C21—S1—C18—C19	0.62 (15)
C10—C11—C12—C13	−0.9 (3)	C21—S1—C18—C17	−178.93 (15)
C11—C12—C13—C14	−179.56 (18)	C17—C18—C19—C20	178.21 (17)
C11—C12—C13—C8	−1.0 (3)	S1—C18—C19—C20	−1.30 (19)
C7—C8—C13—C14	1.5 (3)	C18—C19—C20—C21	1.5 (2)
C9—C8—C13—C14	−178.92 (17)	C19—C20—C21—S1	−1.1 (2)
C7—C8—C13—C12	−177.10 (17)	C18—S1—C21—C20	0.27 (15)

Cg1, Cg2 and Cg3 are the centroids of the S1/C18–C21, C1–C6 and C8–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cg1i	0.91 (3)	2.64 (3)	3.443 (2)	149 (2)
C15—H15A···Cg2ii	0.95 (2)	2.74 (2)	3.565 (2)	146.4 (17)
C21—H21A···Cg3iii	1.04 (3)	2.91 (3)	3.711 (2)	134.4 (19)

Table 1

Hydrogen-bond geometry (Å, °)

Cg 1, Cg 2 and Cg 3 are the centroids of the S1/C18–C21, C1–C6 and C8–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯Cg1i	0.91 (3)	2.64 (3)	3.443 (2)	149 (2)
C15—H15A⋯Cg2ii	0.95 (2)	2.74 (2)	3.565 (2)	146.4 (17)
C21—H21A⋯Cg3iii	1.04 (3)	2.91 (3)	3.711 (2)	134.4 (19)

Symmetry codes: (i) ; (ii) ; (iii) .