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The crystal structure of the 1:1 adduct of 1,2,3,4-tetra­hydro­quinoline (THQ) with 1,3,5-tri­nitro­benzene (TNB), 1,2,3,4-tetra­hydro­quinoline 1,3,5-tri­nitro­benzene (1:1): C6H3N3O6·C9H11N, formed as the sole product from the reaction of THQ with 2,4,6-tri­nitro­benzoic acid (with de­carboxyl­ation), shows stacks comprising π-bonded TNB and THQ mol­ecules linked peripherally by weak hydrogen bonds [N...O 3.170 (3), C...O 3.432 (3) Å].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802016550/ci6154sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802016550/ci6154Isup2.hkl
Contains datablock I

CCDC reference: 198968

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.055
  • wR factor = 0.174
  • Data-to-parameter ratio = 14.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

2,4,6-Trinitrobenzoic acid (TNBA) is a relatively strong organic acid (pKa = 0.65) which has proved useful in the preparation of proton-transfer compounds with Lewis bases, a small number of which have been characterized crystallographically, e.g. with 2-aminopyrimidine (2-AP), [(2-AP)+(TNBA)] (Byriel et al., 1992), with 3-hydroxypyridine (3-HP) [(3-HP)+(TNBA)] (Lynch et al., 1992a), with 2,6-diaminopyridine (DAP), the modulated structure [(DAP)+(TNBA)] (Smith et al., 2000), and with 4-aminobenzoic acid (PABA), three forms, [(PABA)+(TNBA)] (Lynch et al., 1994), the hydrate [(PABA)+(TNBA). (H2O] (Lynch et al., 1992a) and the unusual tri-heteromolecular crystal adduct [(PABA)+(TNBA). 2(PABA)·(TNB)] (where TNB = 1,3,5-trinitrobenzene) (Lynch et al., 1992b). Non-transfer (1:1) compounds with triphenylphosphine oxide (Lynch et al., 1993) and phenylurea (Bott et al., 2000) are also known. As shown in the structure of the tri-crystal compound (Lynch et al., 1992b), which was prepared from the reaction of PABA with TNBA, the latter compound has a tendency to undergo facile decarboxylation (Coffey, 1977) often at a temperature lower than that of the usually employed refluxing conditions in 95% ethanol/water. The co-crystalline reaction products are stable 1:1 adducts involving 1,3,5-trinitrobenzene which associates with the companion molecule through ππ stacking together with weak N—H···O or C—H···O hydrogen bonds between the stacks. Examples of this type of compound are the (1:1) adducts with anthracene (Brown et al., 1964), skatole (Hanson, 1964), indole (Hanson, 1964), azulene (Hanson, 1965), acepleiadylene (Hanson, 1966), 2,4,6-tri(dimethylamino)-1,3,5-triazine (Williams & Wallwork, 1966), 1,3,5-triaminobenzene (Iwasaki & Saito, 1970), 8-hydroxyquinoline (oxine) (Castellano & Prout, 1971), pyrene (Prout & Tickle, 1973), azulene (Mariezcurrena et al.,1999) and with indole-3-acetic acid (Lynch et al., 1991). Adducts with (2:1) stoichiometry are also known [with trans-azobenzene and N-benzylideneaniline (Bar & Bernstein, 1981)].

Reported here is the crystal structure of the 1:1 adduct of 1,2,3,4-tetrahydroquinoline (THQ) with 1,3,5-trinitrobenzene [(THQ)(TNB)], (I), formed as the sole product in the reaction of THQ with 2,4,6-trinitrobenzoic acid (with decarboxylation). The cell dimensions and space group for this compound were reported by Herbstein et al. (1976), who indicated that it was one of an isomorphous set (Herbstein, 1971; Herbstein & Kaftory, 1975) which included the azulene–TNB adduct (Hanson, 1965). The isomorphism is confirmed in the present study [comparative cell data for (I) from Herbstein et al. (1976) are a = 17.02, b = 6.80, c = 14.05 Å, β = 100°, space group P21/a, cf. azulene:TNB (Hanson, 1965): a = 16.39, b = 6.66, c = 13.77 Å, β = 100°, space group P21/a].

Molecular conformation and atom numbering scheme for the individual molecules of (I) are shown in Fig. 1. These alternating TNB and THQ molecules give stacks down the b cell axis, involving ππ interaction between the aromatic ring systems of both molecules as well as the aromatic nitro substituents of TNB (Fig. 2). The aromatic rings are stacked alternatively at centroid–centroid distances of 3.676 (1) and 3.728 (1) Å, respectively. The stacks are linked by N—H (THQ) to O (TNB) and weaker C—H (THQ) to O (TNB) hydrogen bonds [N11···O31, 3.170 (3) Å, N11—H11···O31, 163 (3)°; C61···O12i, 3.432 (3) Å, C61—H61···O12i, 156°; symmetry code: (i) = 1 + x, y, z].

Only minor deviations from planarity in TNB due to rotation of the nitro group is observed [torsion angles C6—C1—N1—O12, C2—C3—N3—O32, C4—C5—N5—O52 being 163.8 (2), 177.9 (2) and −178.8 (2)°, respectively], the largest being with the only unassociated nitro group. The THQ molecule is similar to that found in its 1:1 proton-transfer compound with 3,5-dinitrosalicylic acid (Smith et al., 2002). However, there is significant vibrational disorder in the carbon atoms of the saturated ring of THQ (particularly C21, C31 and C41), largely in the direction of the molecular stacks. The worst of these, C31 was therefore modelled over two disorder sites [C31 (SOF = 0.733) and C31A (SOF = 0.267)]. This phenomenon is probably due to the presence of two possible conformational orientations of this ring, although similar disorder is also present in the isomorphous azulene–TNB adduct (Hansen, 1965) and in other adducts which involve ππ stacking (Herbstein & Kaftory, 1975).

Experimental top

The synthesis of the title compound, (I), was carried out by heating 1 mmol quantities of 2,4,6-trinitrobenzoic acid and 1,2,3,4-tetrahydroquinoline in 50 ml of 80% ethanol/water under reflux for ca 10 min. After concentration to ca 30 ml, partial room temperature evaporation of the hot-filtered solution gave black data crystals suitable for X-ray diffraction.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. Molecular configuration and atom numbering scheme for the individual species in (I), with atoms shown as 40% probability ellipsoids. Only the major conformer of THQ molecule is shown.
[Figure 2] Fig. 2. Packing in the unit cell, viewed down b, showing hydrogen-bonding interactions as broken lines.
1,2,3,4-tetrahydroquinoline–1,3,5-trinitrobenzene (1:1) top
Crystal data top
C9H11N·C6H3N3O6F(000) = 720
Mr = 346.30Dx = 1.453 Mg m3
Monoclinic, P21/cMelting point = 378.9–381.2 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 13.8474 (12) ÅCell parameters from 3297 reflections
b = 6.8830 (6) Åθ = 2.5–27.1°
c = 16.8328 (15) ŵ = 0.12 mm1
β = 99.273 (3)°T = 293 K
V = 1583.4 (2) Å3Block, black
Z = 40.45 × 0.40 × 0.24 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
2519 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 27.5°, θmin = 2.5°
ϕ and ω scansh = 1716
9501 measured reflectionsk = 86
3583 independent reflectionsl = 2121
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.1118P)2 + 0.1838P]
where P = (Fo2 + 2Fc2)/3
3583 reflections(Δ/σ)max < 0.001
240 parametersΔρmax = 0.21 e Å3
6 restraintsΔρmin = 0.24 e Å3
Crystal data top
C9H11N·C6H3N3O6V = 1583.4 (2) Å3
Mr = 346.30Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.8474 (12) ŵ = 0.12 mm1
b = 6.8830 (6) ÅT = 293 K
c = 16.8328 (15) Å0.45 × 0.40 × 0.24 mm
β = 99.273 (3)°
Data collection top
Bruker SMART CCD area detector
diffractometer
2519 reflections with I > 2σ(I)
9501 measured reflectionsRint = 0.055
3583 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0556 restraints
wR(F2) = 0.174H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.21 e Å3
3583 reflectionsΔρmin = 0.24 e Å3
240 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 > 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
xyzUiso*/UeqOcc. (<1)
O110.03141 (10)0.1035 (3)0.19855 (9)0.1181 (6)
O120.06653 (10)0.0722 (3)0.30820 (8)0.1104 (6)
O310.39948 (11)0.3037 (3)0.31929 (9)0.1267 (7)
O320.46076 (10)0.3156 (3)0.21237 (10)0.1216 (7)
O510.25608 (12)0.2106 (2)0.04427 (7)0.0915 (5)
O520.10354 (13)0.1429 (3)0.04884 (8)0.1043 (5)
N10.04922 (10)0.1072 (2)0.23706 (8)0.0669 (4)
N30.39302 (11)0.2886 (2)0.24764 (10)0.0781 (4)
N50.18439 (13)0.1788 (2)0.01271 (8)0.0732 (4)
C10.13178 (11)0.1542 (2)0.19604 (8)0.0529 (4)
C20.22066 (11)0.2001 (2)0.24188 (8)0.0539 (4)
H20.22840.20590.29780.065*
C30.29740 (11)0.2372 (2)0.20113 (9)0.0551 (4)
C40.28861 (12)0.2294 (2)0.11823 (9)0.0581 (4)
H40.34170.25300.09200.070*
C50.19757 (12)0.1851 (2)0.07631 (8)0.0561 (4)
C60.11800 (11)0.1462 (2)0.11318 (9)0.0562 (4)
H60.05740.11570.08340.067*
N110.58851 (13)0.2611 (3)0.45209 (13)0.0995 (6)
C210.56587 (18)0.2660 (4)0.53086 (17)0.1111 (8)
H21A0.50060.21390.53000.133*0.733 (7)
H21B0.56560.40000.54860.133*0.733 (7)
H21C0.54210.14010.54290.133*0.267 (7)
H21D0.51290.35600.53070.133*0.267 (7)
C310.63550 (18)0.1544 (6)0.58906 (19)0.0942 (13)0.733 (7)
H31A0.62630.01680.57800.113*0.733 (7)
H31B0.62210.17860.64300.113*0.733 (7)
C31A0.6464 (3)0.3045 (15)0.5974 (4)0.111 (4)0.267 (7)
H31C0.62800.25880.64730.133*0.267 (7)
H31D0.65720.44350.60210.133*0.267 (7)
C410.73914 (15)0.2078 (3)0.58515 (11)0.0785 (5)
H41A0.78260.11810.61790.094*0.733 (7)
H41B0.75220.33730.60700.094*0.733 (7)
H41C0.73780.07760.60540.094*0.267 (7)
H41D0.79130.27610.61810.094*0.267 (7)
C510.85214 (12)0.1687 (3)0.48272 (13)0.0756 (5)
H510.90350.14980.52490.091*
C610.87092 (18)0.1624 (3)0.40494 (17)0.0908 (7)
H610.93400.13980.39480.109*
C710.7948 (2)0.1900 (3)0.34225 (14)0.0891 (7)
H710.80650.18550.28940.107*
C810.70233 (17)0.2240 (2)0.35760 (11)0.0778 (5)
H810.65170.24380.31490.093*
C910.68250 (12)0.2294 (2)0.43629 (10)0.0626 (4)
C1010.75947 (11)0.2022 (2)0.50010 (10)0.0593 (4)
H110.548 (2)0.280 (3)0.4111 (17)0.110 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O110.0601 (8)0.2011 (19)0.0937 (10)0.0268 (10)0.0142 (7)0.0080 (11)
O120.0874 (9)0.1753 (17)0.0768 (8)0.0026 (10)0.0380 (7)0.0215 (9)
O310.0771 (9)0.232 (2)0.0677 (9)0.0294 (10)0.0019 (7)0.0207 (10)
O320.0581 (8)0.205 (2)0.1048 (11)0.0171 (9)0.0228 (8)0.0043 (11)
O510.1221 (12)0.1034 (10)0.0566 (7)0.0027 (8)0.0375 (8)0.0010 (6)
O520.1131 (11)0.1379 (13)0.0546 (7)0.0006 (9)0.0087 (7)0.0003 (7)
N10.0605 (8)0.0758 (9)0.0681 (8)0.0022 (6)0.0212 (7)0.0067 (7)
N30.0570 (8)0.1083 (12)0.0690 (9)0.0001 (7)0.0105 (7)0.0027 (8)
N50.0992 (12)0.0735 (9)0.0488 (7)0.0089 (8)0.0180 (8)0.0024 (6)
C10.0561 (8)0.0507 (8)0.0541 (8)0.0058 (6)0.0161 (6)0.0000 (6)
C20.0586 (8)0.0593 (9)0.0449 (7)0.0048 (6)0.0116 (6)0.0008 (6)
C30.0513 (8)0.0611 (9)0.0538 (8)0.0037 (6)0.0116 (6)0.0003 (6)
C40.0634 (9)0.0581 (9)0.0572 (8)0.0083 (7)0.0229 (7)0.0039 (7)
C50.0708 (9)0.0534 (8)0.0452 (7)0.0095 (7)0.0127 (7)0.0004 (6)
C60.0589 (8)0.0552 (8)0.0535 (8)0.0051 (6)0.0057 (6)0.0021 (6)
N110.0630 (10)0.1443 (18)0.0872 (13)0.0186 (10)0.0003 (9)0.0048 (11)
C210.0818 (15)0.141 (2)0.119 (2)0.0205 (14)0.0421 (14)0.0041 (16)
C310.088 (2)0.122 (3)0.0817 (19)0.0026 (18)0.0416 (16)0.0040 (19)
C31A0.123 (8)0.123 (9)0.102 (6)0.044 (6)0.067 (6)0.031 (6)
C410.0839 (12)0.0888 (13)0.0615 (10)0.0026 (10)0.0083 (9)0.0076 (9)
C510.0589 (10)0.0671 (10)0.1022 (14)0.0038 (8)0.0171 (9)0.0057 (9)
C610.0905 (14)0.0641 (11)0.133 (2)0.0096 (10)0.0641 (15)0.0082 (11)
C710.137 (2)0.0584 (10)0.0853 (13)0.0222 (11)0.0591 (15)0.0110 (9)
C810.1096 (15)0.0597 (10)0.0632 (10)0.0108 (9)0.0110 (10)0.0015 (8)
C910.0640 (9)0.0587 (9)0.0651 (9)0.0004 (7)0.0103 (7)0.0025 (7)
C1010.0581 (9)0.0581 (8)0.0622 (9)0.0032 (7)0.0114 (7)0.0038 (7)
Geometric parameters (Å, º) top
O11—N11.1976 (18)C21—H21B0.97
O12—N11.2071 (18)C21—H21C0.96
O31—N31.200 (2)C21—H21D0.96
O32—N31.203 (2)C31—C411.493 (3)
O51—N51.219 (2)C31—H31A0.97
O52—N51.210 (2)C31—H31B0.97
N1—C11.464 (2)C31A—C411.490 (4)
N3—C31.469 (2)C31A—H31C0.97
N5—C51.4807 (19)C31A—H31D0.97
C1—C61.378 (2)C41—C1011.503 (2)
C1—C21.380 (2)C41—H41A0.97
C2—C31.378 (2)C41—H41B0.97
C2—H20.93C41—H41C0.96
C3—C41.382 (2)C41—H41D0.96
C4—C51.376 (2)C51—C611.376 (3)
C4—H40.93C51—C1011.381 (2)
C5—C61.375 (2)C51—H510.93
C6—H60.93C61—C711.379 (3)
N11—C911.387 (2)C61—H610.93
N11—C211.411 (3)C71—C811.367 (3)
N11—H110.83 (3)C71—H710.93
C21—C31A1.471 (4)C81—C911.396 (2)
C21—C311.475 (3)C81—H810.93
C21—H21A0.97C91—C1011.398 (2)
O11—N1—O12123.46 (15)H21C—C31—H31A75.2
O11—N1—C1118.71 (14)C21—C31—H31B109.2
O12—N1—C1117.83 (13)C41—C31—H31B109.2
O31—N3—O32123.05 (17)H21C—C31—H31B103.4
O31—N3—C3118.13 (15)H31A—C31—H31B107.9
O32—N3—C3118.82 (16)C21—C31—H41C143.6
O52—N5—O51124.76 (15)C41—C31—H41C37.5
O52—N5—C5117.88 (15)H21C—C31—H41C147.1
O51—N5—C5117.36 (16)H31A—C31—H41C77.4
C6—C1—C2122.73 (14)H31B—C31—H41C101.9
C6—C1—N1118.51 (14)C21—C31A—C41112.3 (4)
C2—C1—N1118.74 (13)C21—C31A—H31C109.1
C3—C2—C1116.99 (13)C41—C31A—H31C109.1
C3—C2—H2121.5C21—C31A—H31D109.1
C1—C2—H2121.5C41—C31A—H31D109.1
C2—C3—C4123.08 (14)H31C—C31A—H31D107.9
C2—C3—N3118.71 (14)C31A—C41—C3141.2 (4)
C4—C3—N3118.21 (14)C31A—C41—C101116.1 (3)
C5—C4—C3116.79 (14)C31—C41—C101111.38 (18)
C5—C4—H4121.6C31A—C41—H41A132.5
C3—C4—H4121.6C31—C41—H41A109.4
C6—C5—C4123.10 (13)C101—C41—H41A109.4
C6—C5—N5118.29 (14)C31A—C41—H41B69.5
C4—C5—N5118.61 (14)C31—C41—H41B109.4
C5—C6—C1117.30 (14)C101—C41—H41B109.4
C5—C6—H6121.4H41A—C41—H41B108.0
C1—C6—H6121.4C31A—C41—H41C107.5
C91—N11—C21122.77 (18)C31—C41—H41C71.4
C91—N11—H11113.6 (18)C101—C41—H41C109.4
C21—N11—H11123.6 (18)H41A—C41—H41C41.4
N11—C21—C31A117.6 (3)H41B—C41—H41C137.4
N11—C21—C31113.0 (2)C31A—C41—H41D106.6
C31A—C21—C3141.8 (4)C31—C41—H41D137.2
N11—C21—H21A109.0C101—C41—H41D108.9
C31A—C21—H21A131.9H41A—C41—H41D69.1
C31—C21—H21A109.0H41B—C41—H41D41.7
N11—C21—H21B109.0H41C—C41—H41D107.9
C31A—C21—H21B68.6C61—C51—C101122.11 (19)
C31—C21—H21B109.0C61—C51—H51118.9
H21A—C21—H21B107.8C101—C51—H51118.9
N11—C21—H21C108.2C51—C61—C71119.03 (18)
C31A—C21—H21C104.2C51—C61—H61120.5
C31—C21—H21C66.4C71—C61—H61120.5
H21A—C21—H21C47.1C81—C71—C61120.18 (18)
H21B—C21—H21C140.7C81—C71—H71119.9
N11—C21—H21D107.3C61—C71—H71119.9
C31A—C21—H21D111.8C71—C81—C91121.16 (19)
C31—C21—H21D139.1C71—C81—H81119.4
H21A—C21—H21D61.9C91—C81—H81119.4
H21B—C21—H21D49.2N11—C91—C81121.35 (17)
H21C—C21—H21D107.1N11—C91—C101119.76 (16)
C21—C31—C41111.9 (2)C81—C91—C101118.90 (16)
C21—C31—H21C38.9C51—C101—C91118.61 (16)
C41—C31—H21C143.2C51—C101—C41121.94 (15)
C21—C31—H31A109.2C91—C101—C41119.45 (15)
C41—C31—H31A109.2
O11—N1—C1—C615.4 (2)N11—C21—C31—C4150.6 (4)
O12—N1—C1—C6163.78 (17)C31A—C21—C31—C4155.6 (4)
O11—N1—C1—C2166.06 (17)N11—C21—C31A—C4138.4 (9)
O12—N1—C1—C214.7 (2)C31—C21—C31A—C4156.1 (5)
C6—C1—C2—C30.5 (2)C21—C31A—C41—C3155.9 (4)
N1—C1—C2—C3177.92 (13)C21—C31A—C41—C10137.3 (9)
C1—C2—C3—C40.2 (2)C21—C31—C41—C31A55.5 (4)
C1—C2—C3—N3179.38 (13)C21—C31—C41—C10150.2 (4)
O31—N3—C3—C22.8 (3)C101—C51—C61—C710.1 (3)
O32—N3—C3—C2177.93 (17)C51—C61—C71—C810.3 (3)
O31—N3—C3—C4176.77 (17)C61—C71—C81—C910.7 (3)
O32—N3—C3—C42.5 (2)C21—N11—C91—C81179.5 (2)
C2—C3—C4—C51.0 (2)C21—N11—C91—C1010.5 (3)
N3—C3—C4—C5178.58 (14)C71—C81—C91—N11179.07 (17)
C3—C4—C5—C61.1 (2)C71—C81—C91—C1011.0 (2)
C3—C4—C5—N5178.88 (13)C61—C51—C101—C910.4 (2)
O52—N5—C5—C61.2 (2)C61—C51—C101—C41179.59 (16)
O51—N5—C5—C6178.86 (15)N11—C91—C101—C51179.27 (17)
O52—N5—C5—C4178.77 (16)C81—C91—C101—C510.8 (2)
O51—N5—C5—C41.1 (2)N11—C91—C101—C410.0 (2)
C4—C5—C6—C10.5 (2)C81—C91—C101—C41179.99 (15)
N5—C5—C6—C1179.56 (12)C31A—C41—C101—C51161.4 (5)
C2—C1—C6—C50.4 (2)C31—C41—C101—C51153.7 (2)
N1—C1—C6—C5178.04 (13)C31A—C41—C101—C9119.4 (5)
C91—N11—C21—C31A20.9 (6)C31—C41—C101—C9125.6 (3)
C91—N11—C21—C3125.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O310.83 (3)2.37 (3)3.170 (3)163 (3)
C61—H61···O12i0.932.563.432 (3)156
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC9H11N·C6H3N3O6
Mr346.30
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)13.8474 (12), 6.8830 (6), 16.8328 (15)
β (°) 99.273 (3)
V3)1583.4 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.45 × 0.40 × 0.24
Data collection
DiffractometerBruker SMART CCD area detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9501, 3583, 2519
Rint0.055
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.174, 1.07
No. of reflections3583
No. of parameters240
No. of restraints6
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.24

Computer programs: SMART (Bruker, 2000), SMART, SAINT (Bruker, 1999), SHELXTL (Bruker, 1997), SHELXTL, PLATON (Spek, 1999).

 

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