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The title compound, C28H20N4O4, is an organic pigment. The mol­ecule has Ci symmetry. Accordingly, the pyridylethyl groups are arranged in a trans fashion across the naphthalene­imide skeleton. The inter­planar distance between the two aromatic systems is 12.846 (2) Å and this clearly indicates a lack of π–πinter­actions, as also shown by similar spectra in solution and in the solid state.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807040767/kp2131sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807040767/kp2131Isup2.hkl
Contains datablock I

CCDC reference: 660335

Key indicators

  • Single-crystal X-ray study
  • T = 93 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.037
  • wR factor = 0.123
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

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Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 68.22 From the CIF: _diffrn_reflns_theta_full 68.22 From the CIF: _reflns_number_total 1909 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2011 Completeness (_total/calc) 94.93% PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.95
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The title compound (PyENI) is an organic pigment which belongs to the category of perylene and perinone pigments (Herbst & Hunger, 1993). The perylene and perinone pigments differ in the central skeleton being perylene or naphthalene, respectively. We were previously involved in the study of the crystal and electronic structures of pyridylethylnaphthaleneimide (PyEPI) (Mizuguchi et al., 2006). In PyEPI there are two structural isomers in the solid state: the cis form (two pyridylethylgroups are on the same side as characterized by vivid red color; Tojo & Mizuguchi, 2002) and the trans form (across the perylene skeleton as characterized by black color; Mizuguchi & Hino, 2005; Hino & Mizuguchi, 2005). Surprising to say, the trans form (black) is found to be easily transformed into the cis one (red) by heating above 373 K for several s. This phase transformation has prompted us to investigate the crystal structure of PyENI in order to study whether the similar phenomenon occurrs at the shorter wavelengths.

The title molecule is centrosymmetric (Fig. 1) and an asymmetric unit comprises a half of the molecule. Therefore, pyridylethyl groups are arranged in a trans fashion across the naphthaleneimide skeleton. The pyridyl rings and naphthaleneimide skeleton are twisted by 9.45 (5)°. The crystal packing of (I) (Fig. 2) is dominated by van der Waals interactions. The present molecular arrangement of PyENI contrasts remarkably with that of PyEPI where the molecules are involved in π ···π interactions with separation distance of about 3.3 - 3.5 Å.

Related literature top

Three related structural studies of the peryleneimide moiety have been reported: the solvent-free compound (Tojo & Mizuguchi, 2002), the phenol-solvated compound (Mizuguchi & Hino, 2005) and the cresol-solvated compound (Hino & Mizuguchi, 2005). For related literature, see: Herbst & Hunger (1993); Mizuguchi et al. (2006).

Experimental top

PyENI was synthesized by reaction of naphthalenetracarboxylic dianhydride with 1,2-(4-pyridyl)diamine in dimethylnaphthalene at 453 K for 7 h according to the method reported (Herbst & Hunger, 1993). Single crystals of PyENI were grown by recrystallization from solution in dimethylsulfoxide. After 36 h platelet crystals suitable for X-ray analysis were obtained.

Refinement top

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.95 and 0.99 A, and Uiso (H) = 1.2 Ueq (C).

Structure description top

The title compound (PyENI) is an organic pigment which belongs to the category of perylene and perinone pigments (Herbst & Hunger, 1993). The perylene and perinone pigments differ in the central skeleton being perylene or naphthalene, respectively. We were previously involved in the study of the crystal and electronic structures of pyridylethylnaphthaleneimide (PyEPI) (Mizuguchi et al., 2006). In PyEPI there are two structural isomers in the solid state: the cis form (two pyridylethylgroups are on the same side as characterized by vivid red color; Tojo & Mizuguchi, 2002) and the trans form (across the perylene skeleton as characterized by black color; Mizuguchi & Hino, 2005; Hino & Mizuguchi, 2005). Surprising to say, the trans form (black) is found to be easily transformed into the cis one (red) by heating above 373 K for several s. This phase transformation has prompted us to investigate the crystal structure of PyENI in order to study whether the similar phenomenon occurrs at the shorter wavelengths.

The title molecule is centrosymmetric (Fig. 1) and an asymmetric unit comprises a half of the molecule. Therefore, pyridylethyl groups are arranged in a trans fashion across the naphthaleneimide skeleton. The pyridyl rings and naphthaleneimide skeleton are twisted by 9.45 (5)°. The crystal packing of (I) (Fig. 2) is dominated by van der Waals interactions. The present molecular arrangement of PyENI contrasts remarkably with that of PyEPI where the molecules are involved in π ···π interactions with separation distance of about 3.3 - 3.5 Å.

Three related structural studies of the peryleneimide moiety have been reported: the solvent-free compound (Tojo & Mizuguchi, 2002), the phenol-solvated compound (Mizuguchi & Hino, 2005) and the cresol-solvated compound (Hino & Mizuguchi, 2005). For related literature, see: Herbst & Hunger (1993); Mizuguchi et al. (2006).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2006); program(s) used to solve structure: SIR2004 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2006).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with the 50% displacement parameters. Unlabelled atoms are related by the symetry code (1 - x, 1 - y, 1 - z).
[Figure 2] Fig. 2. The crystal packing viewed along the axis a. All the H atoms have been omittd for clarity.
N,N'-Bis[2-(4-pyridyl)ethyl]naphthalene-1,8:4,5-bis(dicarboximide) top
Crystal data top
C28H20N4O4F(000) = 496.00
Mr = 476.48Dx = 1.438 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ynCell parameters from 8499 reflections
a = 10.0900 (16) Åθ = 3.6–68.2°
b = 8.8239 (15) ŵ = 0.81 mm1
c = 12.846 (2) ÅT = 93 K
β = 105.811 (10)°Platelet, light brown
V = 1100.5 (3) Å30.50 × 0.14 × 0.13 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1751 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.021
ω scansθmax = 68.2°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1212
Tmin = 0.881, Tmax = 0.900k = 99
9001 measured reflectionsl = 1414
1909 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.1P)2 + 0.2956P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.123(Δ/σ)max < 0.001
S = 0.94Δρmax = 0.20 e Å3
1909 reflectionsΔρmin = 0.28 e Å3
164 parameters
Crystal data top
C28H20N4O4V = 1100.5 (3) Å3
Mr = 476.48Z = 2
Monoclinic, P21/nCu Kα radiation
a = 10.0900 (16) ŵ = 0.81 mm1
b = 8.8239 (15) ÅT = 93 K
c = 12.846 (2) Å0.50 × 0.14 × 0.13 mm
β = 105.811 (10)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1909 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
1751 reflections with F2 > 2σ(F2)
Tmin = 0.881, Tmax = 0.900Rint = 0.021
9001 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037164 parameters
wR(F2) = 0.123H-atom parameters constrained
S = 0.94Δρmax = 0.20 e Å3
1909 reflectionsΔρmin = 0.28 e Å3
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 was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.63037 (9)0.03698 (11)0.08849 (7)0.0236 (2)
O20.82986 (10)0.41491 (11)0.05932 (8)0.0277 (2)
N10.72158 (10)0.18910 (13)0.05892 (8)0.0202 (3)
N20.33163 (12)0.66405 (15)0.21169 (9)0.0314 (3)
C10.72033 (12)0.03121 (16)0.06131 (9)0.0197 (3)
C20.83357 (12)0.04762 (16)0.02935 (9)0.0192 (3)
C30.83190 (13)0.20294 (15)0.01844 (10)0.0213 (3)
C40.94482 (12)0.03810 (16)0.01277 (9)0.0184 (3)
C50.94845 (13)0.19711 (16)0.02271 (9)0.0203 (3)
C61.05903 (13)0.27826 (16)0.00833 (10)0.0222 (3)
C70.83207 (13)0.27835 (16)0.04804 (10)0.0212 (3)
C80.60316 (13)0.27091 (16)0.07764 (10)0.0221 (3)
C90.62031 (13)0.30750 (16)0.19715 (10)0.0243 (3)
C100.51955 (13)0.43001 (15)0.20583 (9)0.0204 (3)
C110.39203 (14)0.39920 (16)0.22266 (11)0.0261 (3)
C120.30364 (14)0.51844 (18)0.22457 (11)0.0304 (3)
C130.45555 (14)0.69295 (16)0.19616 (10)0.0274 (3)
C140.55050 (13)0.58128 (16)0.19223 (10)0.0240 (3)
H30.75660.25960.02910.026*
H61.06150.38530.01650.027*
H8a0.51920.20880.05030.027*
H8b0.59000.36670.03590.027*
H9a0.60320.21540.23560.029*
H9b0.71560.34210.23120.029*
H110.36590.29800.23270.031*
H120.21670.49500.23590.037*
H130.47930.79540.18740.033*
H140.63640.60780.18030.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0208 (4)0.0240 (5)0.0273 (5)0.0029 (3)0.0088 (3)0.0010 (3)
O20.0318 (5)0.0175 (6)0.0382 (5)0.0008 (3)0.0170 (4)0.0012 (3)
N10.0212 (5)0.0191 (7)0.0210 (5)0.0009 (4)0.0073 (4)0.0010 (4)
N20.0288 (6)0.0363 (8)0.0291 (6)0.0069 (5)0.0079 (4)0.0041 (5)
C10.0202 (6)0.0213 (8)0.0166 (6)0.0007 (4)0.0032 (4)0.0001 (4)
C20.0219 (6)0.0184 (7)0.0174 (6)0.0002 (4)0.0053 (4)0.0012 (4)
C30.0218 (6)0.0207 (7)0.0225 (6)0.0027 (4)0.0079 (4)0.0014 (5)
C40.0227 (6)0.0172 (7)0.0156 (6)0.0009 (4)0.0055 (4)0.0010 (4)
C50.0237 (6)0.0190 (8)0.0187 (6)0.0003 (4)0.0067 (5)0.0007 (4)
C60.0267 (6)0.0158 (7)0.0249 (6)0.0011 (4)0.0086 (5)0.0002 (5)
C70.0267 (7)0.0173 (8)0.0205 (6)0.0004 (4)0.0078 (5)0.0007 (4)
C80.0212 (6)0.0217 (7)0.0240 (6)0.0021 (4)0.0071 (4)0.0008 (5)
C90.0250 (6)0.0249 (8)0.0232 (6)0.0026 (5)0.0070 (5)0.0006 (5)
C100.0220 (6)0.0245 (7)0.0149 (5)0.0011 (4)0.0055 (4)0.0025 (4)
C110.0261 (7)0.0286 (8)0.0252 (6)0.0043 (5)0.0097 (5)0.0034 (5)
C120.0222 (6)0.0407 (9)0.0300 (7)0.0016 (5)0.0096 (5)0.0053 (6)
C130.0337 (7)0.0253 (8)0.0230 (6)0.0001 (5)0.0074 (5)0.0025 (5)
C140.0226 (6)0.0298 (8)0.0204 (6)0.0024 (5)0.0070 (5)0.0026 (5)
Geometric parameters (Å, º) top
O1—C11.2168 (16)C6—H60.950
O2—C71.2146 (17)C8—H8a0.990
N1—C11.3937 (18)C8—H8b0.990
N1—C71.4027 (17)C9—C101.5088 (19)
N2—C121.335 (2)C9—H9a0.990
N2—C131.3432 (19)C9—H9b0.990
C1—C21.4878 (18)C10—C111.388 (2)
C2—C31.3773 (19)C10—C141.3926 (19)
C2—C41.4170 (18)C11—C121.384 (2)
C3—C6i1.406 (2)C11—H110.950
C3—H30.950C12—H120.950
C4—C4i1.4138 (18)C13—C141.385 (2)
C4—C51.4085 (19)C13—H130.950
C5—C61.3799 (19)C14—H140.950
C5—C71.4856 (19)
O1···O1ii3.0425 (11)C14···C1viii3.4024 (15)
O1···C1ii3.5379 (13)C14···H8av3.526
O1···C8ii3.4099 (14)C14···H8bv2.923
O1···C9iii3.4669 (14)C14···H9aviii3.564
O1···C13iv3.4688 (17)C14···H9bviii3.251
O1···H8aii2.507H3···O2iv2.965
O1···H9biii2.637H3···C8ii3.515
O1···H13iv2.680H3···C9iii3.447
O1···H14iv3.344H3···C11ii3.403
O1···H14iii3.490H3···H8aii2.727
O2···N2v3.4884 (14)H3···H8bii3.497
O2···C3vi3.4136 (16)H3···H9aiii2.977
O2···C6vii3.1422 (17)H3···H9biii3.146
O2···C12v3.5753 (16)H3···H11ii3.269
O2···H3vi2.965H3···H14iv2.810
O2···H6vii2.417H6···O2vii2.417
O2···H13iii3.463H6···C6vii3.191
N1···C13v3.4385 (15)H6···C7vii3.337
N1···C14iii3.5223 (14)H6···C12xi3.307
N1···H13v3.263H6···H6vii2.352
N1···H14iii3.343H6···H12xi2.987
N2···O2v3.4884 (14)H8a···O1ii2.507
N2···C5viii3.5389 (14)H8a···C1ii3.239
N2···C7v3.3340 (15)H8a···C3ii3.410
N2···C11ix3.339 (2)H8a···C13v3.358
N2···C12ix3.595 (2)H8a···C14v3.526
N2···H8bv3.490H8a···H3ii2.727
N2···H11ix2.580H8a···H13v3.057
N2···H12ix3.066H8a···H14v3.365
C1···O1ii3.5379 (13)H8b···N2v3.490
C1···C10iii3.5150 (14)H8b···C10v3.495
C1···C14iii3.4024 (15)H8b···C13v2.937
C1···H8aii3.239H8b···C14v2.923
C1···H9biii3.060H8b···H3ii3.497
C1···H14iii3.309H8b···H8bv2.963
C2···C10iii3.3257 (15)H8b···H13v3.110
C2···H9aiii3.585H8b···H14v3.087
C2···H9biii3.389H9a···C2viii3.585
C3···O2iv3.4136 (16)H9a···C3viii3.132
C3···C9iii3.5537 (18)H9a···C14iii3.564
C3···H8aii3.410H9a···H3viii2.977
C3···H9aiii3.132H9a···H14iii2.725
C3···H9biii3.401H9b···O1viii2.637
C3···H11ii3.404H9b···C1viii3.060
C4···C11iii3.5657 (17)H9b···C2viii3.389
C5···N2iii3.5389 (14)H9b···C3viii3.401
C5···C13iii3.4749 (16)H9b···C13iii3.453
C5···H11x3.589H9b···C14iii3.251
C6···O2vii3.1422 (17)H9b···H3viii3.146
C6···H6vii3.191H9b···H13iii2.997
C6···H12xi3.492H9b···H14iii2.622
C7···N2v3.3340 (15)H11···N2xii2.580
C7···C13iii3.4814 (16)H11···C3ii3.404
C7···H6vii3.337H11···C5xiv3.589
C7···H13iii3.416H11···C12xii3.134
C8···O1ii3.4099 (14)H11···H3ii3.269
C8···C13v3.4187 (18)H11···H12xii2.862
C8···H3ii3.515H12···N2xii3.066
C8···H13v3.329H12···C6xiii3.492
C9···O1viii3.4669 (14)H12···C13xii3.423
C9···C3viii3.5537 (18)H12···H6xiii2.987
C9···H3viii3.447H12···H11ix2.862
C9···H14iii3.083H12···H13xii3.008
C10···C1viii3.5150 (14)H13···O1vi2.680
C10···C2viii3.3257 (15)H13···O2viii3.463
C10···H8bv3.495H13···N1v3.263
C11···N2xii3.339 (2)H13···C7viii3.416
C11···C4viii3.5657 (17)H13···C8v3.329
C11···H3ii3.403H13···H8av3.057
C12···O2v3.5753 (16)H13···H8bv3.110
C12···N2xii3.595 (2)H13···H9bviii2.997
C12···H6xiii3.307H13···H12ix3.008
C12···H11ix3.134H14···O1vi3.344
C13···O1vi3.4688 (17)H14···O1viii3.490
C13···N1v3.4385 (15)H14···N1viii3.343
C13···C5viii3.4749 (16)H14···C1viii3.309
C13···C7viii3.4814 (16)H14···C9viii3.083
C13···C8v3.4187 (18)H14···H3vi2.810
C13···H8av3.358H14···H8av3.365
C13···H8bv2.937H14···H8bv3.087
C13···H9bviii3.453H14···H9aviii2.725
C13···H12ix3.423H14···H9bviii2.622
C14···N1viii3.5223 (14)
C1—N1—C7125.15 (11)N1—C8—H8a109.0
C1—N1—C8118.32 (10)N1—C8—H8b109.0
C7—N1—C8116.35 (11)C9—C8—H8a109.0
C12—N2—C13115.97 (12)C9—C8—H8b109.0
O1—C1—N1120.84 (12)H8a—C8—H8b107.8
O1—C1—C2122.48 (12)C8—C9—C10109.31 (9)
N1—C1—C2116.68 (11)C8—C9—H9a109.8
C1—C2—C3120.28 (12)C8—C9—H9b109.8
C1—C2—C4119.43 (12)C10—C9—H9a109.8
C3—C2—C4120.27 (12)C10—C9—H9b109.8
C2—C3—C6i120.43 (12)H9a—C9—H9b108.3
C2—C3—H3119.8C9—C10—C11122.88 (12)
C6i—C3—H3119.8C9—C10—C14119.92 (12)
C2—C4—C4i119.16 (12)C11—C10—C14117.14 (12)
C2—C4—C5121.35 (12)C10—C11—C12118.88 (13)
C4i—C4—C5119.48 (12)C10—C11—H11120.6
C4—C5—C6120.45 (12)C12—C11—H11120.6
C4—C5—C7119.87 (12)N2—C12—C11124.77 (14)
C6—C5—C7119.68 (12)N2—C12—H12117.6
C3i—C6—C5120.18 (12)C11—C12—H12117.6
C3i—C6—H6119.9N2—C13—C14123.48 (13)
C5—C6—H6119.9N2—C13—H13118.3
O2—C7—N1120.28 (12)C14—C13—H13118.3
O2—C7—C5123.10 (12)C10—C14—C13119.76 (12)
N1—C7—C5116.62 (11)C10—C14—H14120.1
N1—C8—C9113.10 (9)C13—C14—H14120.1
C1—N1—C7—O2171.45 (10)C2—C3—C6i—C5i0.74 (17)
C1—N1—C7—C58.47 (16)C2—C4—C4i—C5i0.88 (15)
C7—N1—C1—O1167.88 (10)C2—C4—C5—C6178.72 (10)
C7—N1—C1—C212.06 (15)C2—C4—C5—C71.74 (15)
C1—N1—C8—C990.12 (12)C4i—C4—C5—C60.38 (15)
C8—N1—C1—O17.03 (15)C4i—C4—C5—C7179.16 (9)
C8—N1—C1—C2173.03 (9)C5—C4—C4i—C2i0.88 (15)
C7—N1—C8—C985.24 (13)C4—C5—C6—C3i1.20 (16)
C8—N1—C7—O23.55 (16)C4—C5—C7—O2178.82 (11)
C8—N1—C7—C5176.52 (9)C4—C5—C7—N11.10 (15)
C12—N2—C13—C140.61 (17)C6—C5—C7—O21.63 (17)
C13—N2—C12—C110.15 (19)C6—C5—C7—N1178.44 (10)
O1—C1—C2—C36.97 (16)C7—C5—C6—C3i178.35 (10)
O1—C1—C2—C4171.52 (10)N1—C8—C9—C10162.48 (11)
N1—C1—C2—C3173.10 (9)C8—C9—C10—C1195.71 (14)
N1—C1—C2—C48.41 (14)C8—C9—C10—C1481.51 (13)
C1—C2—C3—C6i177.93 (10)C9—C10—C11—C12177.04 (11)
C1—C2—C4—C51.96 (15)C9—C10—C14—C13177.55 (10)
C1—C2—C4—C4i177.15 (9)C11—C10—C14—C130.17 (16)
C3—C2—C4—C5179.55 (10)C14—C10—C11—C120.25 (17)
C3—C2—C4—C4i1.34 (15)C10—C11—C12—N20.3 (2)
C4—C2—C3—C6i0.54 (16)N2—C13—C14—C100.64 (18)
Symmetry codes: (i) x+2, y, z; (ii) x+1, y, z; (iii) x+3/2, y1/2, z+1/2; (iv) x, y1, z; (v) x+1, y+1, z; (vi) x, y+1, z; (vii) x+2, y+1, z; (viii) x+3/2, y+1/2, z+1/2; (ix) x+1/2, y+1/2, z+1/2; (x) x+1/2, y+1/2, z1/2; (xi) x+1, y, z; (xii) x+1/2, y1/2, z+1/2; (xiii) x1, y, z; (xiv) x1/2, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC28H20N4O4
Mr476.48
Crystal system, space groupMonoclinic, P21/n
Temperature (K)93
a, b, c (Å)10.0900 (16), 8.8239 (15), 12.846 (2)
β (°) 105.811 (10)
V3)1100.5 (3)
Z2
Radiation typeCu Kα
µ (mm1)0.81
Crystal size (mm)0.50 × 0.14 × 0.13
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.881, 0.900
No. of measured, independent and
observed [F2 > 2σ(F2)] reflections
9001, 1909, 1751
Rint0.021
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.123, 0.94
No. of reflections1909
No. of parameters164
No. of restraints?
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.28

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2006), SIR2004 (Burla et al., 2003), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996).

 

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