7-Bromo-1-(3-fluoro­phenyl­sulfon­yl)-2-methyl­naphtho­[2,1-b]furan

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536812040470

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o3047

https://doi.org/10.1107/S1600536812040470

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7-Bromo-1-(3-fluorophenylsulfonyl)-2-methylnaphtho[2,1-b]furan

Hong Dae Choi,^a Pil Ja Seo ^a and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong, Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 4 September 2012; accepted 25 September 2012; online 29 September 2012)

In the title compound, C₁₉H₁₂BrFO₃S, the 3-fluorophenyl ring makes a dihedral angle of 80.85 (5)° with the mean plane [r.m.s. deviation = 0.009 (2)Å] of the naphthofuran fragment. In the crystal, molecules are linked by slipped π–π interactions between the furan and the outer benzene rings of neighbouring molecules [centroid–centroid distance = 3.756 (3) Å and slippage of 1.189 (3) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008 , 2011 ).

Experimental

Crystal data

C₁₉H₁₂BrFO₃S
M_r = 419.26
Triclinic, $[P \overline 1]$
a = 7.7141 (2) Å
b = 8.1619 (2) Å
c = 13.4046 (4) Å
α = 74.277 (2)°
β = 86.410 (2)°
γ = 89.044 (2)°
V = 810.80 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.69 mm⁻¹
T = 173 K
0.28 × 0.24 × 0.23 mm

Data collection

Bruker SMART APEX II CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.573, T_max = 0.746
15010 measured reflections
4031 independent reflections
3483 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.075
S = 1.06
4031 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040470/rk2381sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812040470/rk2381Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812040470/rk2381Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 7-bromo-2-methylnaphtho[2,1-b]furan derivatives containing 1-(4-methylphenylsulfonyl) (Choi et al., 2008) and 1-(4-fluorophenylsulfonyl) (Choi et al., 2011) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.009 (2)Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle formed by the mean plane of the naphthofuran ring and the 3-fluorophenyl ring is 80.85 (5)°. In the crystal structure (Fig. 2), molecules are connected by slipped π···π interactions between the furan and outer benzene rings of neighbouring molecules, with a Cg1···Cg2ⁱ distance of 3.756 (3)Å and an interplanar distance of 3.563 (3)Å resulting in a slippage of 1.189 (3)Å (Cg1 and Cg2 are the centroids of the C1/C2/C11/O1/C12 furan ring and the C3–C8 benzene ring, respectively). Symmetry code: (i) -x+2, -y+1, -z+1.

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2011).

Experimental top

The 77% 3-chloroperoxybenzoic acid (336 mg, 1.5 mmol) was added in small portions to a stirred solution of 7-bromo-1-(3-fluorophenylsulfanyl)-2-methylnaphtho[2,1-b]furan (271 mg, 0.7 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 10 h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (benzene) to afford the title compound as a colourless solid - yield 67%, m.p. 472–473 K; Rf = 0.68 (benzene). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Structure description top

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2011).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of π···π interactions (dotted lines) in the crystal structure of the title compound. All H atoms were omitted for clarity. Symmetry code: (i) -x+2, -y+1, -z+1.

7-Bromo-1-(3-fluorophenylsulfonyl)-2-methylnaphtho[2,1-b]furan top

Crystal data top

C₁₉H₁₂BrFO₃S	Z = 2
M_r = 419.26	F(000) = 420
Triclinic, P1	D_x = 1.717 Mg m⁻³
Hall symbol: -P 1	Melting point = 472–473 K
a = 7.7141 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1619 (2) Å	Cell parameters from 7012 reflections
c = 13.4046 (4) Å	θ = 2.6–28.3°
α = 74.277 (2)°	µ = 2.69 mm⁻¹
β = 86.410 (2)°	T = 173 K
γ = 89.044 (2)°	Block, colourless
V = 810.80 (4) Å³	0.28 × 0.24 × 0.23 mm

Data collection top

Bruker SMART APEX II CCD diffractometer	4031 independent reflections
Radiation source: rotating anode	3483 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.047
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 1.6°
φ– and ω–scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −10→10
T_min = 0.573, T_max = 0.746	l = −17→16
15010 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0258P)² + 0.4345P] where P = (F_o² + 2F_c²)/3
4031 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₉H₁₂BrFO₃S	γ = 89.044 (2)°
M_r = 419.26	V = 810.80 (4) Å³
Triclinic, P1	Z = 2
a = 7.7141 (2) Å	Mo Kα radiation
b = 8.1619 (2) Å	µ = 2.69 mm⁻¹
c = 13.4046 (4) Å	T = 173 K
α = 74.277 (2)°	0.28 × 0.24 × 0.23 mm
β = 86.410 (2)°

Data collection top

Bruker SMART APEX II CCD diffractometer	4031 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3483 reflections with I > 2σ(I)
T_min = 0.573, T_max = 0.746	R_int = 0.047
15010 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.06	Δρ_max = 0.49 e Å⁻³
4031 reflections	Δρ_min = −0.40 e Å⁻³
227 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.57980 (3)	0.18645 (3)	0.314671 (17)	0.03502 (8)
S1	0.84031 (6)	0.35008 (6)	0.82867 (4)	0.02420 (11)
F1	0.3382 (2)	−0.0623 (2)	0.89171 (12)	0.0539 (4)
O1	0.90963 (19)	0.80950 (18)	0.64831 (11)	0.0290 (3)
O2	0.92123 (19)	0.21364 (19)	0.79427 (12)	0.0314 (3)
O3	0.90169 (19)	0.3885 (2)	0.91876 (11)	0.0325 (3)
C1	0.8517 (2)	0.5360 (2)	0.72789 (15)	0.0234 (4)
C2	0.8204 (2)	0.5642 (2)	0.61823 (15)	0.0225 (4)
C3	0.7631 (2)	0.4684 (2)	0.55178 (15)	0.0215 (4)
C4	0.7185 (3)	0.2941 (2)	0.58317 (15)	0.0261 (4)
H4	0.7272	0.2323	0.6538	0.031*
C5	0.6630 (3)	0.2119 (3)	0.51466 (16)	0.0275 (4)
H5	0.6325	0.0948	0.5376	0.033*
C6	0.6516 (2)	0.3023 (3)	0.41023 (16)	0.0253 (4)
C7	0.6938 (3)	0.4703 (3)	0.37573 (16)	0.0270 (4)
H7	0.6852	0.5286	0.3045	0.032*
C8	0.7502 (2)	0.5582 (2)	0.44463 (15)	0.0234 (4)
C9	0.7940 (3)	0.7335 (3)	0.40720 (16)	0.0274 (4)
H9	0.7845	0.7893	0.3357	0.033*
C10	0.8488 (3)	0.8229 (3)	0.47063 (16)	0.0276 (4)
H10	0.8790	0.9399	0.4456	0.033*
C11	0.8588 (2)	0.7340 (2)	0.57511 (16)	0.0247 (4)
C12	0.9047 (3)	0.6874 (3)	0.74099 (16)	0.0277 (4)
C13	0.9565 (3)	0.7507 (3)	0.82888 (19)	0.0394 (5)
H13A	1.0769	0.7176	0.8436	0.059*
H13B	0.8801	0.7012	0.8906	0.059*
H13C	0.9467	0.8751	0.8104	0.059*
C14	0.6173 (2)	0.2986 (3)	0.85656 (14)	0.0238 (4)
C15	0.5063 (3)	0.4128 (3)	0.88799 (16)	0.0289 (4)
H15	0.5463	0.5223	0.8879	0.035*
C16	0.3356 (3)	0.3642 (3)	0.91954 (17)	0.0354 (5)
H16	0.2575	0.4416	0.9404	0.043*
C17	0.2788 (3)	0.2043 (3)	0.92085 (17)	0.0363 (5)
H17	0.1623	0.1704	0.9431	0.044*
C18	0.3928 (3)	0.0953 (3)	0.88949 (17)	0.0349 (5)
C19	0.5630 (3)	0.1383 (3)	0.85604 (16)	0.0298 (4)
H19	0.6394	0.0612	0.8336	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.04802 (14)	0.03053 (13)	0.02960 (12)	−0.00014 (9)	−0.00906 (9)	−0.01191 (9)
S1	0.0227 (2)	0.0285 (3)	0.0205 (2)	0.00142 (18)	−0.00143 (18)	−0.00511 (19)
F1	0.0640 (10)	0.0522 (9)	0.0498 (9)	−0.0291 (8)	0.0038 (8)	−0.0209 (7)
O1	0.0344 (8)	0.0268 (7)	0.0263 (7)	−0.0069 (6)	0.0010 (6)	−0.0084 (6)
O2	0.0297 (7)	0.0319 (8)	0.0309 (8)	0.0074 (6)	−0.0006 (6)	−0.0064 (6)
O3	0.0311 (7)	0.0439 (9)	0.0238 (7)	−0.0008 (7)	−0.0066 (6)	−0.0101 (7)
C1	0.0226 (9)	0.0264 (10)	0.0206 (9)	−0.0019 (7)	0.0018 (7)	−0.0061 (8)
C2	0.0218 (9)	0.0231 (9)	0.0219 (9)	0.0006 (7)	0.0024 (7)	−0.0055 (7)
C3	0.0180 (8)	0.0241 (9)	0.0217 (9)	0.0011 (7)	0.0024 (7)	−0.0056 (7)
C4	0.0311 (10)	0.0240 (10)	0.0215 (9)	0.0004 (8)	0.0007 (8)	−0.0039 (8)
C5	0.0335 (10)	0.0218 (10)	0.0264 (10)	−0.0009 (8)	−0.0005 (8)	−0.0052 (8)
C6	0.0244 (9)	0.0295 (10)	0.0245 (10)	0.0013 (8)	−0.0028 (8)	−0.0114 (8)
C7	0.0288 (10)	0.0285 (10)	0.0223 (10)	0.0029 (8)	−0.0028 (8)	−0.0044 (8)
C8	0.0220 (9)	0.0249 (10)	0.0219 (9)	0.0014 (7)	0.0005 (7)	−0.0047 (8)
C9	0.0302 (10)	0.0261 (10)	0.0224 (10)	0.0008 (8)	−0.0013 (8)	−0.0007 (8)
C10	0.0286 (10)	0.0228 (10)	0.0288 (10)	−0.0038 (8)	0.0022 (8)	−0.0030 (8)
C11	0.0233 (9)	0.0248 (10)	0.0263 (10)	−0.0028 (7)	0.0017 (8)	−0.0081 (8)
C12	0.0275 (10)	0.0310 (11)	0.0249 (10)	−0.0034 (8)	0.0034 (8)	−0.0090 (8)
C13	0.0503 (14)	0.0389 (13)	0.0328 (12)	−0.0120 (11)	−0.0007 (10)	−0.0160 (10)
C14	0.0245 (9)	0.0287 (10)	0.0161 (9)	−0.0011 (8)	−0.0013 (7)	−0.0021 (7)
C15	0.0287 (10)	0.0309 (11)	0.0250 (10)	0.0022 (8)	−0.0013 (8)	−0.0041 (8)
C16	0.0276 (10)	0.0470 (14)	0.0281 (11)	0.0073 (10)	0.0001 (9)	−0.0050 (10)
C17	0.0250 (10)	0.0559 (15)	0.0252 (11)	−0.0068 (10)	−0.0041 (8)	−0.0053 (10)
C18	0.0413 (12)	0.0402 (12)	0.0224 (10)	−0.0150 (10)	−0.0042 (9)	−0.0056 (9)
C19	0.0363 (11)	0.0321 (11)	0.0209 (10)	−0.0009 (9)	−0.0005 (8)	−0.0075 (8)

Geometric parameters (Å, º) top

Br1—C6	1.8986 (19)	C7—H7	0.9500
S1—O2	1.4358 (15)	C8—C9	1.421 (3)
S1—O3	1.4363 (15)	C9—C10	1.351 (3)
S1—C1	1.736 (2)	C9—H9	0.9500
S1—C14	1.770 (2)	C10—C11	1.398 (3)
F1—C18	1.352 (3)	C10—H10	0.9500
O1—C12	1.365 (3)	C12—C13	1.487 (3)
O1—C11	1.371 (2)	C13—H13A	0.9800
C1—C12	1.367 (3)	C13—H13B	0.9800
C1—C2	1.460 (3)	C13—H13C	0.9800
C2—C11	1.378 (3)	C14—C19	1.382 (3)
C2—C3	1.428 (3)	C14—C15	1.386 (3)
C3—C4	1.412 (3)	C15—C16	1.388 (3)
C3—C8	1.434 (3)	C15—H15	0.9500
C4—C5	1.367 (3)	C16—C17	1.379 (3)
C4—H4	0.9500	C16—H16	0.9500
C5—C6	1.402 (3)	C17—C18	1.369 (3)
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.361 (3)	C18—C19	1.380 (3)
C7—C8	1.406 (3)	C19—H19	0.9500

O2—S1—O3	118.58 (9)	C9—C10—C11	116.43 (19)
O2—S1—C1	109.57 (9)	C9—C10—H10	121.8
O3—S1—C1	107.58 (9)	C11—C10—H10	121.8
O2—S1—C14	107.07 (9)	O1—C11—C2	111.44 (17)
O3—S1—C14	106.73 (9)	O1—C11—C10	122.61 (18)
C1—S1—C14	106.70 (9)	C2—C11—C10	125.94 (19)
C12—O1—C11	107.20 (15)	O1—C12—C1	109.96 (17)
C12—C1—C2	107.40 (17)	O1—C12—C13	113.53 (18)
C12—C1—S1	122.42 (15)	C1—C12—C13	136.5 (2)
C2—C1—S1	130.10 (15)	C12—C13—H13A	109.5
C11—C2—C3	118.08 (18)	C12—C13—H13B	109.5
C11—C2—C1	104.00 (17)	H13A—C13—H13B	109.5
C3—C2—C1	137.92 (18)	C12—C13—H13C	109.5
C4—C3—C2	125.37 (18)	H13A—C13—H13C	109.5
C4—C3—C8	117.97 (18)	H13B—C13—H13C	109.5
C2—C3—C8	116.66 (17)	C19—C14—C15	121.94 (19)
C5—C4—C3	121.73 (18)	C19—C14—S1	118.52 (15)
C5—C4—H4	119.1	C15—C14—S1	119.23 (16)
C3—C4—H4	119.1	C14—C15—C16	118.7 (2)
C4—C5—C6	119.28 (19)	C14—C15—H15	120.6
C4—C5—H5	120.4	C16—C15—H15	120.6
C6—C5—H5	120.4	C17—C16—C15	120.5 (2)
C7—C6—C5	121.39 (18)	C17—C16—H16	119.8
C7—C6—Br1	119.44 (15)	C15—C16—H16	119.8
C5—C6—Br1	119.15 (15)	C18—C17—C16	118.9 (2)
C6—C7—C8	120.53 (18)	C18—C17—H17	120.5
C6—C7—H7	119.7	C16—C17—H17	120.5
C8—C7—H7	119.7	F1—C18—C17	119.1 (2)
C7—C8—C9	119.75 (18)	F1—C18—C19	118.0 (2)
C7—C8—C3	119.09 (18)	C17—C18—C19	122.9 (2)
C9—C8—C3	121.16 (18)	C18—C19—C14	117.1 (2)
C10—C9—C8	121.72 (19)	C18—C19—H19	121.5
C10—C9—H9	119.1	C14—C19—H19	121.5
C8—C9—H9	119.1

O2—S1—C1—C12	−132.60 (17)	C12—O1—C11—C2	0.1 (2)
O3—S1—C1—C12	−2.4 (2)	C12—O1—C11—C10	179.98 (18)
C14—S1—C1—C12	111.81 (17)	C3—C2—C11—O1	179.17 (16)
O2—S1—C1—C2	43.6 (2)	C1—C2—C11—O1	−0.1 (2)
O3—S1—C1—C2	173.78 (17)	C3—C2—C11—C10	−0.7 (3)
C14—S1—C1—C2	−72.00 (19)	C1—C2—C11—C10	−179.99 (19)
C12—C1—C2—C11	0.1 (2)	C9—C10—C11—O1	−178.91 (18)
S1—C1—C2—C11	−176.57 (15)	C9—C10—C11—C2	1.0 (3)
C12—C1—C2—C3	−178.9 (2)	C11—O1—C12—C1	0.0 (2)
S1—C1—C2—C3	4.4 (3)	C11—O1—C12—C13	−179.86 (17)
C11—C2—C3—C4	−179.95 (18)	C2—C1—C12—O1	0.0 (2)
C1—C2—C3—C4	−1.0 (4)	S1—C1—C12—O1	176.92 (13)
C11—C2—C3—C8	0.0 (3)	C2—C1—C12—C13	179.8 (2)
C1—C2—C3—C8	178.9 (2)	S1—C1—C12—C13	−3.3 (4)
C2—C3—C4—C5	179.37 (18)	O2—S1—C14—C19	8.63 (18)
C8—C3—C4—C5	−0.5 (3)	O3—S1—C14—C19	−119.31 (16)
C3—C4—C5—C6	0.6 (3)	C1—S1—C14—C19	125.89 (16)
C4—C5—C6—C7	−0.3 (3)	O2—S1—C14—C15	−177.62 (15)
C4—C5—C6—Br1	178.52 (15)	O3—S1—C14—C15	54.44 (18)
C5—C6—C7—C8	−0.1 (3)	C1—S1—C14—C15	−60.36 (18)
Br1—C6—C7—C8	−178.92 (14)	C19—C14—C15—C16	−0.1 (3)
C6—C7—C8—C9	179.91 (18)	S1—C14—C15—C16	−173.67 (16)
C6—C7—C8—C3	0.2 (3)	C14—C15—C16—C17	0.9 (3)
C4—C3—C8—C7	0.1 (3)	C15—C16—C17—C18	−0.7 (3)
C2—C3—C8—C7	−179.79 (17)	C16—C17—C18—F1	179.29 (19)
C4—C3—C8—C9	−179.58 (17)	C16—C17—C18—C19	−0.3 (3)
C2—C3—C8—C9	0.5 (3)	F1—C18—C19—C14	−178.59 (18)
C7—C8—C9—C10	−179.96 (19)	C17—C18—C19—C14	1.0 (3)
C3—C8—C9—C10	−0.2 (3)	C15—C14—C19—C18	−0.7 (3)
C8—C9—C10—C11	−0.5 (3)	S1—C14—C19—C18	172.82 (15)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₂BrFO₃S
M_r	419.26
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.7141 (2), 8.1619 (2), 13.4046 (4)
α, β, γ (°)	74.277 (2), 86.410 (2), 89.044 (2)
V (Å³)	810.80 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.69
Crystal size (mm)	0.28 × 0.24 × 0.23

Data collection
Diffractometer	Bruker SMART APEX II CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.573, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	15010, 4031, 3483
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.075, 1.06
No. of reflections	4031
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.40

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan city.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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