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Acta Crystallogr Sect E Struct Rep Online. 2009 February 1; 65(Pt 2): m198–m199.
Published online 2009 January 17. doi:  10.1107/S1600536809001421
PMCID: PMC2968341

Bis{6,6′-dimeth­oxy-2,2′-[ethane-1,2-diyl­bis(imino­methyl­ene)]diphenolato(1.5−)-κ4 O,N,N′,O′}erbium(III)

Abstract

In the title compound, [Er(C18H22.5N2O4)2], the Er atom is located on a twofold rotation axis and is eight-coordinated by four O atoms and four N atoms from two symmetry-related 6,6′-dimethoxy-2,2′-(ethane-1,2-diyldiiminodimethylene)diphenolate(1.5−) ligands. Due to disorder of one phenolate H atom with half-occupation, the overall charge of one tetradentate ligand is −1.5. The ligand molecules are stabilised by intramolecular N—H(...)O and O—H(...)O hydrogen bonds and are linked into a chain parallel to the a axis by a C—H(...)O hydrogen bond. Neighbouring chains are connected by van der Waals forces, resulting in a three-dimensional network.

Related literature

For related structures, see: Liu et al. (2007 [triangle]); Xia et al. (2006 [triangle]). For isotypic structures, see: Xia et al. (2009a [triangle], 2009b [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m198-scheme1.jpg

Experimental

Crystal data

  • [Er(C18H22.5N2O4)2]
  • M r = 829.02
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m198-efi1.jpg
  • a = 11.1542 (10) Å
  • b = 21.958 (2) Å
  • c = 14.1751 (15) Å
  • V = 3471.8 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 2.48 mm−1
  • T = 298 (2) K
  • 0.20 × 0.15 × 0.14 mm

Data collection

  • Siemens SMART 1000 CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.637, T max = 0.723
  • 7986 measured reflections
  • 3007 independent reflections
  • 2199 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.162
  • S = 1.06
  • 3007 reflections
  • 224 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.75 e Å−3
  • Δρmin = −1.42 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1400 Friedel pairs
  • Flack parameter: 0.02 (5)

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001421/at2680sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001421/at2680Isup2.hkl

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

Acknowledgments

We acknowledge the financial support of the Huaihai Institute of Technology Science Foundation.

supplementary crystallographic information

Comment

Diamine derivatives are potentially multidentate ligands. We have recently reported the crystal structure (C18H24O2N4) (II) (Xia et al., 2006) which is the ligand of the title compound and a complex [Ce(C18H22N2O4)2] (III) (Liu et al., 2007). We report here the crystal structure of new rare earth complex (I).

In the title complex (I), the coordination environment of the Er atom and coordination modes of (I) ligands to ErIII ion is in agreement with the complexes reported above (Fig. 1). The average bond lengths of between the Erbium center oxygen atoms are 2.203 (6)Å and nitrogen atom are 2.612 (8) Å, longer than the 2.199 (4)Å and shorter than the 2.624 (4)Å of complexes (III), respectively. The dihedral angles between phenyl ring (C2-C7 ring) and anotother phenyl ring are 42.20 (28)°(C10—C15 ring), 42.29 (26)°(C2A—C7A ring) and 15.47 (43)°(C10A—C15A ring) [symmetry codes: (A) 2 - x, 2 - y, z].

In (I), the Er atom is eight-coordinated by four O atoms and four N atoms from two 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene)diphenol. The molecules are linked into a chain parallel to the a axis by one C—H···O hydrogen bond. Neighbouring chains are connected by van der Waals forces, resulting in a three-dimensional network.

Experimental

A solution of 6,6'-dimethoxy-2,2'-(ethane-1,2-diyldiiminodimethylene) diphenol (0.328 g, 2 mmol) in ethanol (20 ml), and then a solution of Er(NO3)3.6H2O (0.461 g, 1 mmol) in ethanol (10 ml) was added. The reaction mixture was stirred for 3 h in the air and then filtered. X-ray quality crystals of (I) were obtained by evaporation of an ethanol solution.

Refinement

The space group was uniquely assigned from the systematic absences. All H atoms were located in difference Fourier maps. H atoms bonded to C, O and N atoms were treated as riding atoms, with C—H distances of 0.93 Å (aryl), 0.96 Å (methyl), 0.97Å (methylene) and N—H distances of 0.90 Å (amino), Uiso(H) = 1.2Ueq(aryl, methylene, NH) or 1.5Ueq(C) (methyl or OH). The H1 bonded to O1 is disordered and were refined with the occupancies ties to 0.5.

Figures

Fig. 1.
The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are at the 30% probability level. For clarity, H atoms have been omitted. [symmetry codes: (A) 2 - x, 2 - y, z].
Fig. 2.
A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded chain built from C—H···O. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen ...

Crystal data

[Er(C18H22.5N2O4)2]F(000) = 1684
Mr = 829.02Dx = 1.586 Mg m3
Orthorhombic, Iba2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: I 2 -2cCell parameters from 4129 reflections
a = 11.1542 (10) Åθ = 2.9–25.7°
b = 21.958 (2) ŵ = 2.48 mm1
c = 14.1751 (15) ÅT = 298 K
V = 3471.8 (6) Å3Block, brown
Z = 40.20 × 0.15 × 0.14 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer3007 independent reflections
Radiation source: fine-focus sealed tube2199 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −13→10
Tmin = 0.637, Tmax = 0.723k = −20→26
7986 measured reflectionsl = −16→16

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.162w = 1/[σ2(Fo2) + (0.1143P)2 + 1.9553P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
3007 reflectionsΔρmax = 0.75 e Å3
224 parametersΔρmin = −1.42 e Å3
1 restraintAbsolute structure: Flack (1983), 1400 Freidel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.02 (5)

Special details

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)

xyzUiso*/UeqOcc. (<1)
Er11.00001.00000.0158 (2)0.0342 (2)
O10.9418 (5)1.0681 (3)0.1202 (4)0.0297 (13)
H10.99191.09550.12090.045*0.50
O20.9141 (6)1.1865 (3)0.0933 (5)0.0479 (18)
O31.1356 (6)0.9653 (3)−0.0834 (5)0.0389 (16)
O41.3687 (7)0.9386 (4)−0.0660 (7)0.065 (3)
N10.7906 (7)0.9657 (4)0.0823 (6)0.040 (2)
H1C0.73580.98380.04390.048*
N20.9283 (8)0.8957 (4)−0.0492 (6)0.043 (2)
H20.96730.8670−0.01460.052*
C10.7624 (12)0.9901 (6)0.1789 (10)0.049 (3)
H1A0.69060.97060.20290.058*
H1B0.82790.98090.22160.058*
C20.7440 (9)1.0568 (5)0.1748 (7)0.042 (3)
C30.8366 (9)1.0926 (5)0.1404 (7)0.039 (3)
C40.8159 (9)1.1552 (5)0.1290 (7)0.041 (2)
C50.7089 (10)1.1808 (6)0.1508 (8)0.051 (3)
H50.69571.22230.14290.061*
C60.6169 (10)1.1415 (7)0.1866 (9)0.056 (3)
H60.54281.15820.20210.067*
C70.6330 (9)1.0854 (7)0.1977 (9)0.057 (3)
H70.57081.06180.22160.068*
C80.8935 (13)1.2474 (5)0.0637 (10)0.064 (3)
H8A0.81121.25190.04510.095*
H8B0.94471.25670.01120.095*
H8C0.91071.27470.11490.095*
C90.9606 (16)0.8829 (7)−0.1469 (9)0.061 (4)
H9A0.94550.9184−0.18600.073*
H9B0.91350.8492−0.17090.073*
C101.0949 (14)0.8668 (6)−0.1482 (8)0.054 (3)
C111.1731 (11)0.9109 (5)−0.1134 (7)0.043 (3)
C121.2992 (13)0.8958 (6)−0.1052 (8)0.056 (3)
C131.3345 (14)0.8375 (6)−0.1369 (9)0.063 (4)
H131.41490.8264−0.13330.076*
C141.2544 (16)0.7976 (7)−0.1721 (10)0.070 (4)
H141.28040.7590−0.18970.084*
C151.1369 (14)0.8120 (6)−0.1826 (9)0.066 (4)
H151.08500.7852−0.21280.079*
C161.4901 (11)0.9202 (11)−0.0443 (19)0.092 (7)
H16A1.53260.9538−0.01670.139*
H16B1.52980.9078−0.10130.139*
H16C1.48850.8868−0.00070.139*
C170.7704 (9)0.9017 (5)0.0703 (9)0.051 (3)
H17A0.68760.89200.08490.061*
H17B0.82160.87890.11270.061*
C180.7979 (11)0.8845 (5)−0.0316 (10)0.052 (3)
H18A0.77920.8419−0.04220.063*
H18B0.74980.9089−0.07430.063*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Er10.0382 (3)0.0267 (3)0.0377 (3)0.0000 (2)0.0000.000
O10.018 (3)0.033 (4)0.038 (3)0.003 (3)0.005 (3)−0.004 (3)
O20.053 (4)0.035 (4)0.055 (4)0.009 (3)0.001 (3)−0.007 (3)
O30.056 (4)0.026 (4)0.034 (4)0.014 (3)0.011 (3)−0.001 (3)
O40.055 (5)0.055 (6)0.085 (7)0.019 (4)0.031 (4)0.023 (5)
N10.031 (4)0.038 (5)0.052 (5)−0.009 (4)−0.007 (4)0.012 (4)
N20.051 (6)0.026 (4)0.052 (5)−0.003 (4)−0.024 (4)0.003 (4)
C10.041 (6)0.055 (8)0.050 (7)−0.002 (5)0.001 (5)0.017 (5)
C20.032 (5)0.048 (7)0.046 (6)0.008 (5)0.005 (4)0.005 (5)
C30.036 (6)0.045 (7)0.036 (6)0.005 (5)−0.009 (4)−0.003 (5)
C40.043 (6)0.041 (6)0.040 (5)0.010 (5)−0.008 (5)−0.004 (5)
C50.046 (6)0.051 (7)0.055 (7)0.018 (6)−0.003 (5)−0.006 (5)
C60.042 (7)0.066 (9)0.060 (8)0.019 (6)0.007 (5)0.007 (6)
C70.036 (6)0.071 (10)0.063 (8)0.006 (6)0.015 (5)0.010 (7)
C80.079 (9)0.025 (6)0.087 (9)−0.003 (6)0.010 (7)0.008 (6)
C90.086 (9)0.045 (8)0.052 (8)−0.001 (7)−0.019 (7)−0.007 (6)
C100.084 (9)0.036 (6)0.043 (6)0.015 (6)−0.005 (6)−0.003 (5)
C110.063 (8)0.041 (7)0.024 (6)0.021 (6)0.007 (5)0.010 (5)
C120.076 (9)0.047 (7)0.045 (6)0.029 (7)0.021 (6)0.011 (6)
C130.084 (10)0.051 (9)0.056 (8)0.034 (8)0.022 (7)0.011 (6)
C140.104 (12)0.049 (8)0.057 (8)0.024 (8)0.011 (7)−0.003 (7)
C150.105 (12)0.045 (8)0.047 (7)0.019 (7)−0.005 (7)−0.011 (6)
C160.060 (10)0.089 (15)0.128 (17)0.026 (7)0.030 (8)0.031 (13)
C170.037 (6)0.040 (7)0.075 (10)−0.011 (5)−0.017 (6)0.013 (6)
C180.057 (7)0.023 (6)0.076 (8)−0.016 (5)−0.029 (6)0.011 (5)

Geometric parameters (Å, °)

Er1—O3i2.202 (6)C5—C61.433 (19)
Er1—O32.202 (6)C5—H50.9300
Er1—O12.203 (6)C6—C71.254 (19)
Er1—O1i2.203 (6)C6—H60.9300
Er1—N22.595 (8)C7—H70.9300
Er1—N2i2.595 (8)C8—H8A0.9600
Er1—N1i2.628 (8)C8—H8B0.9600
Er1—N12.628 (8)C8—H8C0.9600
O1—C31.321 (12)C9—C101.54 (2)
O1—H10.8200C9—H9A0.9700
O2—C41.389 (13)C9—H9B0.9700
O2—C81.419 (14)C10—C151.379 (17)
O3—C111.334 (13)C10—C111.394 (19)
O4—C121.340 (16)C11—C121.450 (17)
O4—C161.446 (16)C12—C131.412 (17)
N1—C171.433 (14)C13—C141.35 (2)
N1—C11.504 (16)C13—H130.9300
N1—H1C0.9094C14—C151.36 (2)
N2—C91.458 (16)C14—H140.9300
N2—C181.495 (15)C15—H150.9300
N2—H20.9105C16—H16A0.9600
C1—C21.479 (15)C16—H16B0.9600
C1—H1A0.9700C16—H16C0.9600
C1—H1B0.9700C17—C181.523 (17)
C2—C31.387 (15)C17—H17A0.9700
C2—C71.426 (15)C17—H17B0.9700
C3—C41.404 (15)C18—H18A0.9700
C4—C51.355 (15)C18—H18B0.9700
O3i—Er1—O3100.6 (4)C5—C4—C3121.7 (11)
O3i—Er1—O189.5 (2)O2—C4—C3113.4 (8)
O3—Er1—O1150.1 (2)C4—C5—C6117.5 (12)
O3i—Er1—O1i150.1 (2)C4—C5—H5121.3
O3—Er1—O1i89.5 (2)C6—C5—H5121.3
O1—Er1—O1i95.6 (3)C7—C6—C5122.2 (11)
O3i—Er1—N282.4 (3)C7—C6—H6118.9
O3—Er1—N271.3 (3)C5—C6—H6118.9
O1—Er1—N2138.4 (3)C6—C7—C2121.9 (12)
O1i—Er1—N274.3 (2)C6—C7—H7119.1
O3i—Er1—N2i71.3 (3)C2—C7—H7119.1
O3—Er1—N2i82.4 (3)O2—C8—H8A109.5
O1—Er1—N2i74.3 (2)O2—C8—H8B109.5
O1i—Er1—N2i138.4 (3)H8A—C8—H8B109.5
N2—Er1—N2i138.4 (4)O2—C8—H8C109.5
O3i—Er1—N1i137.8 (3)H8A—C8—H8C109.5
O3—Er1—N1i73.6 (2)H8B—C8—H8C109.5
O1—Er1—N1i80.0 (2)N2—C9—C10107.3 (10)
O1i—Er1—N1i72.0 (2)N2—C9—H9A110.3
N2—Er1—N1i130.8 (3)C10—C9—H9A110.3
N2i—Er1—N1i66.5 (3)N2—C9—H9B110.3
O3i—Er1—N173.6 (2)C10—C9—H9B110.3
O3—Er1—N1137.8 (3)H9A—C9—H9B108.5
O1—Er1—N172.0 (2)C15—C10—C11121.3 (13)
O1i—Er1—N180.0 (2)C15—C10—C9122.4 (12)
N2—Er1—N166.5 (3)C11—C10—C9116.4 (10)
N2i—Er1—N1130.8 (3)O3—C11—C10122.6 (10)
N1i—Er1—N1138.0 (4)O3—C11—C12118.9 (11)
C3—O1—Er1133.1 (6)C10—C11—C12118.4 (11)
C3—O1—H1107.7O4—C12—C13127.4 (13)
Er1—O1—H1107.7O4—C12—C11115.7 (10)
C4—O2—C8116.5 (9)C13—C12—C11116.9 (14)
C11—O3—Er1136.7 (7)C14—C13—C12121.5 (14)
C12—O4—C16115.7 (13)C14—C13—H13119.3
C17—N1—C1115.1 (9)C12—C13—H13119.3
C17—N1—Er1112.2 (6)C13—C14—C15121.9 (13)
C1—N1—Er1114.2 (7)C13—C14—H14119.0
C17—N1—H1C104.5C15—C14—H14119.0
C1—N1—H1C104.4C14—C15—C10119.6 (14)
Er1—N1—H1C105.0C14—C15—H15120.2
C9—N2—C18111.6 (10)C10—C15—H15120.2
C9—N2—Er1115.5 (8)O4—C16—H16A109.5
C18—N2—Er1112.7 (6)O4—C16—H16B109.5
C9—N2—H2105.1H16A—C16—H16B109.5
C18—N2—H2105.1O4—C16—H16C109.5
Er1—N2—H2105.8H16A—C16—H16C109.5
C2—C1—N1110.2 (9)H16B—C16—H16C109.5
C2—C1—H1A109.6N1—C17—C18108.9 (9)
N1—C1—H1A109.6N1—C17—H17A109.9
C2—C1—H1B109.6C18—C17—H17A109.9
N1—C1—H1B109.6N1—C17—H17B109.9
H1A—C1—H1B108.1C18—C17—H17B109.9
C3—C2—C7118.5 (11)H17A—C17—H17B108.3
C3—C2—C1118.1 (10)N2—C18—C17108.3 (8)
C7—C2—C1123.2 (10)N2—C18—H18A110.0
O1—C3—C2120.5 (10)C17—C18—H18A110.0
O1—C3—C4121.3 (9)N2—C18—H18B110.0
C2—C3—C4118.2 (9)C17—C18—H18B110.0
C5—C4—O2124.9 (10)H18A—C18—H18B108.4
O3i—Er1—O1—C333.8 (8)Er1—O1—C3—C264.0 (13)
O3—Er1—O1—C3144.6 (8)Er1—O1—C3—C4−116.8 (9)
O1i—Er1—O1—C3−116.7 (9)C7—C2—C3—O1178.5 (10)
N2—Er1—O1—C3−44.0 (10)C1—C2—C3—O1−6.0 (15)
N2i—Er1—O1—C3104.5 (9)C7—C2—C3—C4−0.7 (15)
N1i—Er1—O1—C3172.7 (9)C1—C2—C3—C4174.8 (10)
N1—Er1—O1—C3−39.1 (8)C8—O2—C4—C5−10.6 (15)
O3i—Er1—O3—C11−106.2 (10)C8—O2—C4—C3168.9 (10)
O1—Er1—O3—C11145.9 (9)O1—C3—C4—C5−179.0 (10)
O1i—Er1—O3—C1145.5 (10)C2—C3—C4—C50.2 (16)
N2—Er1—O3—C11−28.1 (9)O1—C3—C4—O21.5 (14)
N2i—Er1—O3—C11−175.4 (10)C2—C3—C4—O2−179.3 (9)
N1i—Er1—O3—C11116.9 (10)O2—C4—C5—C6179.7 (10)
N1—Er1—O3—C11−29.0 (11)C3—C4—C5—C60.2 (17)
O3i—Er1—N1—C17107.2 (7)C4—C5—C6—C70(2)
O3—Er1—N1—C1719.4 (8)C5—C6—C7—C20(2)
O1—Er1—N1—C17−157.9 (7)C3—C2—C7—C60.9 (18)
O1i—Er1—N1—C17−58.7 (7)C1—C2—C7—C6−174.4 (13)
N2—Er1—N1—C1718.5 (6)C18—N2—C9—C10−154.4 (9)
N2i—Er1—N1—C17153.1 (7)Er1—N2—C9—C1075.2 (10)
N1i—Er1—N1—C17−107.1 (7)N2—C9—C10—C15122.1 (13)
O3i—Er1—N1—C1−119.5 (7)N2—C9—C10—C11−58.5 (14)
O3—Er1—N1—C1152.8 (6)Er1—O3—C11—C1052.0 (14)
O1—Er1—N1—C1−24.5 (7)Er1—O3—C11—C12−124.9 (10)
O1i—Er1—N1—C174.7 (7)C15—C10—C11—O3177.0 (10)
N2—Er1—N1—C1151.9 (7)C9—C10—C11—O3−2.4 (16)
N2i—Er1—N1—C1−73.6 (8)C15—C10—C11—C12−6.0 (17)
N1i—Er1—N1—C126.3 (6)C9—C10—C11—C12174.5 (9)
O3i—Er1—N2—C969.5 (9)C16—O4—C12—C13−7.5 (19)
O3—Er1—N2—C9−34.5 (9)C16—O4—C12—C11170.7 (12)
O1—Er1—N2—C9150.1 (8)O3—C11—C12—O40.9 (14)
O1i—Er1—N2—C9−129.4 (9)C10—C11—C12—O4−176.1 (11)
N2i—Er1—N2—C919.2 (8)O3—C11—C12—C13179.3 (10)
N1i—Er1—N2—C9−81.1 (9)C10—C11—C12—C132.3 (15)
N1—Er1—N2—C9144.9 (9)O4—C12—C13—C14177.5 (12)
O3i—Er1—N2—C18−60.3 (7)C11—C12—C13—C14−0.7 (17)
O3—Er1—N2—C18−164.3 (7)C12—C13—C14—C153(2)
O1—Er1—N2—C1820.2 (8)C13—C14—C15—C10−6(2)
O1i—Er1—N2—C18100.8 (7)C11—C10—C15—C148(2)
N2i—Er1—N2—C18−110.7 (7)C9—C10—C15—C14−172.5 (12)
N1i—Er1—N2—C18149.1 (6)C1—N1—C17—C18177.7 (9)
N1—Er1—N2—C1815.1 (6)Er1—N1—C17—C18−49.4 (9)
C17—N1—C1—C2−159.7 (9)C9—N2—C18—C17−177.3 (10)
Er1—N1—C1—C268.3 (10)Er1—N2—C18—C17−45.5 (9)
N1—C1—C2—C3−58.1 (13)N1—C17—C18—N263.8 (10)
N1—C1—C2—C7117.1 (12)

Symmetry codes: (i) −x+2, −y+2, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16A···O4ii0.962.703.49 (3)140
N2—H2···O2i0.912.343.230 (10)166
N1—H1C···O4i0.912.593.462 (12)162
O1—H1···O20.822.212.646 (9)113

Symmetry codes: (ii) −x+3, −y+2, z; (i) −x+2, −y+2, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2680).

References

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