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In the title compound, C15H16NO2+·0.58Br·0.42I, the cation is essentially planar, the dihedral angle between the two aromatic rings being 2.59 (18)°. The cations are linked into zigzag chains along the b axis by weak C—H...O hydrogen bonds, and the chains are linked to form a three-dimensional framework by O—H...Br, O—H...I (H...I = 1.97–2.48 Å) and C—H...I (H...I = 2.47–2.91 Å) hydrogen bonds, and π–π inter­actions involving the pyridinium and benzene rings [centroid–centroid distance is 3.518 (2) Å]. A single anion site is occupied at random by Br or I.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022076/ci2384sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022076/ci2384Isup2.hkl
Contains datablock I

CCDC reference: 651420

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in main residue
  • R factor = 0.072
  • wR factor = 0.216
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT432_ALERT_2_A Short Inter X...Y Contact I1A .. C12 .. 3.16 Ang.
Author Response: This may be due to the presence of disorder of the idione and bromine atoms. Otherwise I am at a loss to offer any other explanation.

Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact I1B .. C15 .. 3.31 Ang.
Author Response: This may be due to the presence of disorder of the idione and bromine atoms. Otherwise I am at a loss to offer any other explanation.
PLAT432_ALERT_2_B Short Inter X...Y Contact  I1C    ..  C7      ..       3.36 Ang.
Author Response: This may be due to the presence of disorder of the idione and bromine atoms. Otherwise I am at a loss to offer any other explanation.
PLAT432_ALERT_2_B Short Inter X...Y Contact  I1C    ..  C14     ..       3.37 Ang.
Author Response: This may be due to the presence of disorder of the idione and bromine atoms. Otherwise I am at a loss to offer any other explanation.

Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT077_ALERT_4_C Unitcell contains non-integer number of atoms .. ? PLAT301_ALERT_3_C Main Residue Disorder ......................... 5.00 Perc. PLAT431_ALERT_2_C Short Inter HL..A Contact I1A .. N1 .. 3.30 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact I1C .. C5 .. 3.41 Ang.
Author Response: This may be due to the presence of disorder of the idione and bromine atoms. Otherwise I am at a loss to offer any other explanation.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          1

Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
1 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

In recent years, much effort has been focused on the development of new materials with non-linear optical (NLO) properties (Patil et al., 2006; Shettigar et al., 2006). In our continuing systamatic study of NLO materials (Jindawong et al., 2005; Chantrapromma et al., 2005; Chantrapromma, Ruanwas, Fun et al., 2006; Chantrapromma, Jindawong & Fun, 2006; Chantrapromma, Ruanwas, Jindawong et al., 2006; Fun et al., 2006; Ruanwas et al., 2007; Chantrapromma et al., 2007), the title compound, (I), was synthesized and its crystal structure is reported here. Compound (I) crystallizes in a centrosymmetric space group and this precludes the presence of second-order NLO properties.

The refinement of (I) revealed the composition to be C15H16NO2+.0.58Br-.0.42I- (Fig. 1), i.e. with fractional occupancy of the halide ions. Moreover, the iodide ion is disordered over three sites (I1A, I1B and I1C in Fig. 1). The cation exists in an E configuration with respect to the C7C8 double bond [1.330 (6) Å], with the torsion angle C6–C7–C8–C9 being -178.8 (3)°. The bond lengths and angles (Table 1) have normal values (Allen et al., 1987) and comparable to those in related structures (Jindawong et al., 2005; Chantrapromma et al., 2005; Chantrapromma, Ruanwas, Fun et al., 2006; Chantrapromma, Jindawong & Fun, 2006; Chantrapromma, Ruanwas, Jindawong et al., 2006; Ruanwas et al., 2007; Chantrapromma et al., 2007). The cation is essentially planar, the dihedral angle between the pyridinium and benzene rings is 2.59 (18)°. The C14—O2—C4—C5 torsion angle of -5.6 (6)° shows that the methoxy group is slightly twisted out of the benzene ring plane.

Intermolecular O—H···Br hydrogen bonds and weak C—H···O interactions are observed in the crystal structure of (I) (Table 1). The cations are linked together in a head-to-tail manner into zigzag chains along the b axis through weak C—H···O interactions, and these chains are cross-linked by O—H···Br, O—H···I (H···I = 1.97–2.48 Å) and C—H···I (H···I = 2.47–2.91 Å) interactions forming a three-dimensional network (Fig. 2). The centroid-centroid distance between the N1/C9–C13 ring at (x, y, z) and the C1–C6 benzene ring at (2 - x, -y, -1 - z) is 3.518 (2) Å, indicating π-π interactions. A C12···I1A(-x, 1 - y, 1 - z) short contact [3.156 (7) Å] is observed in the crystal structure.

Related literature top

For bond-length data, see: Allen et al. (1987). For related structures, see: Jindawong et al. (2005); Chantrapromma et al. (2005); Chantrapromma, Ruanwas, Fun et al. (2006); Chantrapromma, Jindawong & Fun (2006); Chantrapromma, Ruanwas, Jindawong et al. (2006); Fun et al. (2006); Ruanwas et al. (2007); Chantrapromma et al. (2007); Patil et al. (2006); Shettigar et al. (2006).

Experimental top

Silver(I) 4-bromobenzenesulfonate (0.20 g, 0.59 mmol) in hot methanol (50 ml) was added to a solution of 4-(4'-hydroxy-3'-methoxystyryl)-1-methylpyridinium iodide (0.22 g, 0.59 mmol) in hot methanol (40 ml). The mixture immediately yielded a yellow solid of silver iodide which was filtered off after stirring the mixture for 30 min. The resulting red solution was evaporated to yield a red-brown solid. Brown block-shaped single crystals of (I) were obtained by recrystallization from methanol-ethanol (1:1 v/v) at room temperature after several days.

Refinement top

The site occupancy factors for atoms Br1, I1A, I1B and I1C refined to 0.580 (3), 0.133 (2), 0.139 (2) and 0.148 (2), respectively. H atoms were placed in calculated positions, with O—H distance of 0.82 Å and C—H distances in the range 0.93–0.96 Å. The Uiso values were constrained to be 1.5Ueq of the carrier atom for hydroxyl and methyl H atoms and 1.2Ueq for the remaining H atoms. A rotating group model was used for the methyl groups. Owing to the large fraction of weak data at higher angles, the 2θ maximum was limited to 52°. The highest residual density peak is located 0.68 Å from atom C13 and the deepest hole is located 0.57 Å from atom Br1.

Structure description top

In recent years, much effort has been focused on the development of new materials with non-linear optical (NLO) properties (Patil et al., 2006; Shettigar et al., 2006). In our continuing systamatic study of NLO materials (Jindawong et al., 2005; Chantrapromma et al., 2005; Chantrapromma, Ruanwas, Fun et al., 2006; Chantrapromma, Jindawong & Fun, 2006; Chantrapromma, Ruanwas, Jindawong et al., 2006; Fun et al., 2006; Ruanwas et al., 2007; Chantrapromma et al., 2007), the title compound, (I), was synthesized and its crystal structure is reported here. Compound (I) crystallizes in a centrosymmetric space group and this precludes the presence of second-order NLO properties.

The refinement of (I) revealed the composition to be C15H16NO2+.0.58Br-.0.42I- (Fig. 1), i.e. with fractional occupancy of the halide ions. Moreover, the iodide ion is disordered over three sites (I1A, I1B and I1C in Fig. 1). The cation exists in an E configuration with respect to the C7C8 double bond [1.330 (6) Å], with the torsion angle C6–C7–C8–C9 being -178.8 (3)°. The bond lengths and angles (Table 1) have normal values (Allen et al., 1987) and comparable to those in related structures (Jindawong et al., 2005; Chantrapromma et al., 2005; Chantrapromma, Ruanwas, Fun et al., 2006; Chantrapromma, Jindawong & Fun, 2006; Chantrapromma, Ruanwas, Jindawong et al., 2006; Ruanwas et al., 2007; Chantrapromma et al., 2007). The cation is essentially planar, the dihedral angle between the pyridinium and benzene rings is 2.59 (18)°. The C14—O2—C4—C5 torsion angle of -5.6 (6)° shows that the methoxy group is slightly twisted out of the benzene ring plane.

Intermolecular O—H···Br hydrogen bonds and weak C—H···O interactions are observed in the crystal structure of (I) (Table 1). The cations are linked together in a head-to-tail manner into zigzag chains along the b axis through weak C—H···O interactions, and these chains are cross-linked by O—H···Br, O—H···I (H···I = 1.97–2.48 Å) and C—H···I (H···I = 2.47–2.91 Å) interactions forming a three-dimensional network (Fig. 2). The centroid-centroid distance between the N1/C9–C13 ring at (x, y, z) and the C1–C6 benzene ring at (2 - x, -y, -1 - z) is 3.518 (2) Å, indicating π-π interactions. A C12···I1A(-x, 1 - y, 1 - z) short contact [3.156 (7) Å] is observed in the crystal structure.

For bond-length data, see: Allen et al. (1987). For related structures, see: Jindawong et al. (2005); Chantrapromma et al. (2005); Chantrapromma, Ruanwas, Fun et al. (2006); Chantrapromma, Jindawong & Fun (2006); Chantrapromma, Ruanwas, Jindawong et al. (2006); Fun et al. (2006); Ruanwas et al. (2007); Chantrapromma et al. (2007); Patil et al. (2006); Shettigar et al. (2006).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The packing diagram of (I), viewed along the c axis. Hydrogen bonds are shown as dashed lines.
4-(4'-Hydroxy-3'-methoxystyryl)-1-methylpyridinium 0.58-bromide 0.42-iodide top
Crystal data top
C15H16NO2+·0.58Br·0.42IF(000) = 686.2
Mr = 341.93Dx = 1.554 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2857 reflections
a = 8.9627 (13) Åθ = 2.0–26.0°
b = 20.721 (3) ŵ = 2.55 mm1
c = 8.0865 (12) ÅT = 297 K
β = 103.304 (2)°Block, brown
V = 1461.5 (4) Å30.51 × 0.25 × 0.21 mm
Z = 4
Data collection top
Siemens SMART CCD area-detector
diffractometer
2857 independent reflections
Radiation source: fine-focus sealed tube2417 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 2.0°
ω scansh = 911
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 2519
Tmin = 0.458, Tmax = 0.583l = 99
7691 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.216H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.1083P)2 + 1.625P]
where P = (Fo2 + 2Fc2)/3
2857 reflections(Δ/σ)max = 0.001
206 parametersΔρmax = 0.31 e Å3
1 restraintΔρmin = 0.72 e Å3
Crystal data top
C15H16NO2+·0.58Br·0.42IV = 1461.5 (4) Å3
Mr = 341.93Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.9627 (13) ŵ = 2.55 mm1
b = 20.721 (3) ÅT = 297 K
c = 8.0865 (12) Å0.51 × 0.25 × 0.21 mm
β = 103.304 (2)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
2857 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2417 reflections with I > 2σ(I)
Tmin = 0.458, Tmax = 0.583Rint = 0.024
7691 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0721 restraint
wR(F2) = 0.216H-atom parameters constrained
S = 1.08Δρmax = 0.31 e Å3
2857 reflectionsΔρmin = 0.72 e Å3
206 parameters
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
I1A0.6170 (7)0.6319 (3)0.7668 (8)0.155 (3)0.133 (2)
I1B0.7345 (9)0.6386 (3)0.5754 (7)0.181 (3)0.139 (2)
I1C0.8589 (6)0.6382 (3)0.8253 (8)0.169 (3)0.148 (2)
Br10.72947 (12)0.63747 (4)0.73911 (13)0.0761 (5)0.580 (3)
O10.3913 (3)0.68060 (15)0.4999 (4)0.0709 (9)
H1O10.46270.66420.56910.106*
O20.1697 (3)0.71700 (14)0.2545 (3)0.0596 (7)
N10.4889 (3)0.35571 (15)0.1165 (4)0.0504 (7)
C10.1803 (5)0.5284 (2)0.4242 (5)0.0553 (9)
H10.18630.48630.46510.066*
C20.2924 (5)0.5724 (2)0.4963 (5)0.0570 (9)
H20.37280.55970.58500.068*
C30.2858 (4)0.63491 (19)0.4377 (5)0.0524 (9)
C40.1610 (4)0.65448 (18)0.3036 (4)0.0477 (8)
C50.0524 (4)0.61018 (19)0.2341 (4)0.0491 (8)
H50.02860.62280.14600.059*
C60.0588 (4)0.54602 (19)0.2915 (4)0.0495 (8)
C70.0532 (4)0.4967 (2)0.2190 (5)0.0537 (9)
H70.03990.45640.27120.064*
C80.1721 (4)0.50257 (19)0.0869 (5)0.0520 (9)
H80.18890.54260.03400.062*
C90.2779 (4)0.45054 (18)0.0196 (4)0.0480 (8)
C100.4000 (4)0.46270 (19)0.1185 (5)0.0534 (9)
H100.41200.50360.16700.064*
C110.5017 (4)0.4153 (2)0.1830 (5)0.0549 (9)
H110.58210.42450.27540.066*
C120.3730 (4)0.3415 (2)0.0155 (5)0.0555 (9)
H120.36450.30010.06100.067*
C130.2664 (4)0.3878 (2)0.0845 (5)0.0542 (9)
H130.18580.37710.17520.065*
C140.0455 (5)0.7404 (2)0.1262 (6)0.0681 (11)
H14A0.06670.78380.09690.102*
H14B0.04670.73980.16750.102*
H14C0.03250.71340.02740.102*
C150.6045 (6)0.3056 (2)0.1849 (7)0.0761 (13)
H15A0.55490.26930.22280.114*
H15B0.67930.32310.27880.114*
H15C0.65430.29210.09760.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I1A0.109 (4)0.178 (5)0.180 (5)0.002 (3)0.034 (3)0.028 (4)
I1B0.219 (7)0.194 (6)0.120 (4)0.030 (4)0.020 (4)0.007 (3)
I1C0.126 (4)0.189 (6)0.171 (5)0.004 (3)0.010 (3)0.020 (3)
Br10.0675 (7)0.0599 (5)0.0894 (7)0.0047 (4)0.0053 (4)0.0109 (4)
O10.0550 (17)0.0665 (18)0.078 (2)0.0038 (14)0.0127 (14)0.0072 (15)
O20.0544 (15)0.0577 (16)0.0601 (16)0.0027 (12)0.0003 (12)0.0014 (12)
N10.0451 (16)0.0563 (18)0.0500 (17)0.0027 (13)0.0113 (13)0.0026 (13)
C10.062 (2)0.058 (2)0.0466 (19)0.0003 (18)0.0145 (16)0.0046 (16)
C20.055 (2)0.066 (2)0.0457 (19)0.0013 (18)0.0042 (16)0.0014 (17)
C30.0466 (19)0.061 (2)0.0462 (19)0.0006 (16)0.0038 (15)0.0058 (16)
C40.0447 (18)0.055 (2)0.0432 (18)0.0010 (15)0.0092 (14)0.0044 (15)
C50.0424 (18)0.064 (2)0.0412 (17)0.0029 (16)0.0100 (14)0.0041 (15)
C60.0476 (18)0.059 (2)0.0452 (18)0.0052 (16)0.0183 (15)0.0057 (15)
C70.053 (2)0.059 (2)0.053 (2)0.0001 (17)0.0202 (16)0.0015 (16)
C80.053 (2)0.055 (2)0.051 (2)0.0003 (16)0.0182 (16)0.0003 (16)
C90.0468 (18)0.055 (2)0.0464 (18)0.0003 (15)0.0185 (14)0.0044 (15)
C100.056 (2)0.053 (2)0.053 (2)0.0045 (17)0.0145 (16)0.0008 (16)
C110.0475 (19)0.066 (2)0.050 (2)0.0035 (17)0.0082 (15)0.0028 (17)
C120.054 (2)0.057 (2)0.057 (2)0.0007 (17)0.0155 (17)0.0038 (17)
C130.0486 (19)0.065 (2)0.048 (2)0.0043 (17)0.0080 (15)0.0018 (17)
C140.066 (3)0.062 (2)0.068 (3)0.003 (2)0.001 (2)0.006 (2)
C150.072 (3)0.074 (3)0.076 (3)0.023 (2)0.003 (2)0.004 (2)
Geometric parameters (Å, º) top
O1—C31.351 (5)C7—H70.93
O1—H1O10.82C8—C91.456 (5)
O2—C41.363 (5)C8—H80.93
O2—C141.421 (5)C9—C101.395 (5)
N1—C121.340 (5)C9—C131.397 (5)
N1—C111.341 (5)C10—C111.359 (6)
N1—C151.480 (5)C10—H100.93
C1—C21.383 (6)C11—H110.93
C1—C61.390 (5)C12—C131.378 (6)
C1—H10.93C12—H120.93
C2—C31.375 (6)C13—H130.93
C2—H20.93C14—H14A0.96
C3—C41.426 (5)C14—H14B0.96
C4—C51.362 (5)C14—H14C0.96
C5—C61.405 (6)C15—H15A0.96
C5—H50.93C15—H15B0.96
C6—C71.458 (5)C15—H15C0.96
C7—C81.330 (6)
C3—O1—H1O1109.5C9—C8—H8117.8
C4—O2—C14116.7 (3)C10—C9—C13116.4 (3)
C12—N1—C11120.0 (3)C10—C9—C8119.3 (3)
C12—N1—C15119.5 (4)C13—C9—C8124.3 (3)
C11—N1—C15120.5 (4)C11—C10—C9120.7 (4)
C2—C1—C6121.0 (4)C11—C10—H10119.7
C2—C1—H1119.5C9—C10—H10119.7
C6—C1—H1119.5N1—C11—C10121.6 (4)
C3—C2—C1120.4 (4)N1—C11—H11119.2
C3—C2—H2119.8C10—C11—H11119.2
C1—C2—H2119.8N1—C12—C13120.6 (4)
O1—C3—C2124.1 (4)N1—C12—H12119.7
O1—C3—C4116.3 (3)C13—C12—H12119.7
C2—C3—C4119.6 (3)C12—C13—C9120.7 (4)
C5—C4—O2127.1 (3)C12—C13—H13119.6
C5—C4—C3118.9 (4)C9—C13—H13119.6
O2—C4—C3113.9 (3)O2—C14—H14A109.5
C4—C5—C6122.0 (3)O2—C14—H14B109.5
C4—C5—H5119.0H14A—C14—H14B109.5
C6—C5—H5119.0O2—C14—H14C109.5
C1—C6—C5118.0 (3)H14A—C14—H14C109.5
C1—C6—C7118.1 (4)H14B—C14—H14C109.5
C5—C6—C7123.9 (3)N1—C15—H15A109.5
C8—C7—C6127.5 (4)N1—C15—H15B109.5
C8—C7—H7116.2H15A—C15—H15B109.5
C6—C7—H7116.2N1—C15—H15C109.5
C7—C8—C9124.4 (4)H15A—C15—H15C109.5
C7—C8—H8117.8H15B—C15—H15C109.5
C6—C1—C2—C30.0 (6)C1—C6—C7—C8176.2 (4)
C1—C2—C3—O1179.3 (4)C5—C6—C7—C83.1 (6)
C1—C2—C3—C41.0 (6)C6—C7—C8—C9178.8 (3)
C14—O2—C4—C55.7 (6)C7—C8—C9—C10179.2 (3)
C14—O2—C4—C3177.4 (3)C7—C8—C9—C130.7 (6)
O1—C3—C4—C5179.0 (3)C13—C9—C10—C110.7 (5)
C2—C3—C4—C51.3 (5)C8—C9—C10—C11179.2 (3)
O1—C3—C4—O21.8 (5)C12—N1—C11—C100.7 (6)
C2—C3—C4—O2178.5 (3)C15—N1—C11—C10177.7 (4)
O2—C4—C5—C6177.4 (3)C9—C10—C11—N10.2 (6)
C3—C4—C5—C60.5 (5)C11—N1—C12—C130.1 (5)
C2—C1—C6—C50.7 (5)C15—N1—C12—C13178.2 (4)
C2—C1—C6—C7178.6 (3)N1—C12—C13—C90.8 (6)
C4—C5—C6—C10.4 (5)C10—C9—C13—C121.2 (5)
C4—C5—C6—C7178.8 (3)C8—C9—C13—C12178.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···Br10.822.533.321 (3)162
C12—H12···O1i0.932.523.338 (5)146
Symmetry code: (i) x, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC15H16NO2+·0.58Br·0.42I
Mr341.93
Crystal system, space groupMonoclinic, P21/c
Temperature (K)297
a, b, c (Å)8.9627 (13), 20.721 (3), 8.0865 (12)
β (°) 103.304 (2)
V3)1461.5 (4)
Z4
Radiation typeMo Kα
µ (mm1)2.55
Crystal size (mm)0.51 × 0.25 × 0.21
Data collection
DiffractometerSiemens SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.458, 0.583
No. of measured, independent and
observed [I > 2σ(I)] reflections
7691, 2857, 2417
Rint0.024
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.072, 0.216, 1.08
No. of reflections2857
No. of parameters206
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.72

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O1···Br10.822.533.321 (3)162
C12—H12···O1i0.932.523.338 (5)146
Symmetry code: (i) x, y1/2, z+1/2.
 

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