metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

Crystal structure of poly[[[μ4-5-(9H-carbazol-9-yl)isophthalato][μ3-5-(9H-carbazol-9-yl)isophthalato]bis­­(di­methyl­formamide)(methanol)dizinc] di­methyl­formamide monosolvate]

aDepartment of Chemistry and Center for Photochemical Sciences, Bowling Green State University, Bowling Green, OH 43403, USA, and bBruker AXS Inc., Madison, Wisconsin, USA
*Correspondence e-mail: jkloster@bgsu.edu

Edited by M. Weil, Vienna University of Technology, Austria (Received 26 June 2015; accepted 22 July 2015; online 31 July 2015)

The structure of the polymeric title compound, {[Zn2(C20H11NO4)2(C3H7NO)2(CH3OH)]·C3H7NO}n, comprises carbazolylisophthalate moieties connecting dimetallic tetra­carboxyl­ate zinc secondary building units (SBUs) parallel to [100] and [010], leading to a layer-like arrangement parallel to (001). Each SBU consists of two Zn atoms in slightly distorted tetra­hedral and octa­hedral coordination environments [Zn⋯Zn = 3.5953 (6) Å]. Three carboxyl­ate groups bridge the two Zn atoms in a μ2-O:O′ mode, whereas the fourth coordinates through a single carboxyl­ate O atom (μ1-O). The O atoms of two di­methyl­formamide (DMF) and one methanol mol­ecule complete the Zn coordination spheres. The methanol ligand inter­acts with the noncoordinating DMF mol­ecule via an O—H⋯O hydrogen bond of medium strength. Carbazoles between the layers inter­digitate through weak C—H⋯.π inter­actions to form a laminar solid stacked along [010]. Two kinds of C—H⋯π inter­actions are present, both with a distance of 2.64 Å, between the H atoms and the centroids, and a third C—H⋯π inter­action, where the aromatic H atom is located above the carbazole N-atom lone pair (H⋯N = 2.89 Å). Several C—H⋯O inter­actions occur between the coordinating DMF mol­ecule, the DMF solvent mol­ecule, and ligating carboxyl­ate O atoms.

1. Related literature

For solid-state emission behavior and inter­molecular packing inter­actions for a closely related compound where methanol is replaced by ethanol, see: Lifshits et al. (2015[Lifshits, L. M., Noll, B. C. & Klosterman, J. K. (2015). Chem. Commun. 51, 11603-11606.]). This compound and the title compound are solvatomorphs with identical space groups and comparable lattice parameters. Except for the identity of the coordinating solvent, viz. MeOH versus EtOH, the other structural components are the same.

[Scheme 1]

2. Experimental

2.1. Crystal data

  • [Zn2(C20H11NO4)2(C3H7NO)2(CH3OH)]·C3H7NO

  • Mr = 1040.66

  • Orthorhombic, P 21 21 21

  • a = 10.2867 (4) Å

  • b = 17.0328 (7) Å

  • c = 26.8808 (11) Å

  • V = 4709.8 (3) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 1.84 mm−1

  • T = 100 K

  • 0.40 × 0.22 × 0.22 mm

2.2. Data collection

  • Bruker D8 Venture CMOS diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2015[Bruker (2015). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.53, Tmax = 0.68

  • 41928 measured reflections

  • 8611 independent reflections

  • 8561 reflections with I > 2σ(I)

  • Rint = 0.019

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.019

  • wR(F2) = 0.045

  • S = 1.08

  • 8611 reflections

  • 629 parameters

  • 546 restraints

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.18 e Å−3

  • Absolute structure: Flack x determined using 3716 quotients [(I+) − (I)]/[(I+) + (I)] (Parsons et al, 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])

  • Absolute structure parameter: 0.005 (3)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg3, Cg4 and Cg6 are the centroids of the N1/C1/C6/C7/C12, C1–C6, C7–C12 and C21–C26 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
O12—H12O⋯O11 0.76 1.93 2.696 (2) 174
C42—H42B⋯O11i 0.98 2.52 3.327 (3) 139
C43—H43⋯O10 0.95 2.44 3.028 (3) 120
C46—H46⋯O5 0.95 2.39 2.995 (2) 121
C47—H47B⋯O3ii 0.98 2.61 3.417 (3) 140
C47—H47C⋯O9iii 0.98 2.65 3.608 (3) 165
C2—H2⋯Cg6iv 0.95 2.64 3.517 (2) 153
C10—H10⋯Cg3v 0.95 2.64 3.418 (2) 139
C44—H44BCg4vi 0.98 2.91 3.596 (2) 128
C45—H45BCg1vi 0.98 2.85 3.411 (2) 117
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) [-x+{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}]; (v) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (vi) [-x+{\script{3\over 2}}, -y+2, z+{\script{1\over 2}}].

Data collection: APEX3 (Bruker, 2015[Bruker (2015). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2015[Bruker (2015). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]); molecular graphics: ShelXle (Hübschle et al., 2011[Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281-1284.]); software used to prepare material for publication: APEX3.

Supporting information


Synthesis and crystallization top

The title compound was prepared in an analogous manner to Zn Cbz - EtOH (Lifshits et al., 2015). Single crystals were obtained by the solvothermal reaction of 5-(9H-carbazol-9-yl)-isophthalic acid and zinc nitrate in DMF/MeOH at room temperature overnight.

Refinement top

All H-atom positions were located from difference maps, then refined with isotropic temperature factors. Subsequently, positional restraints were added for all hydrogen atoms and Uiso values for hydrogen atoms were restrained to 1.2Ueq of the attached atom.

Related literature top

For solid-state emission behavior and intermolecular packing interactions for a closely related compound where methanol is replaced by ethanol, see: Lifshits et al. (2015). This compound and the title compound are solvatomorphs with identical space groups type and comparable lattice parameters. Except for the identity of the coordinating solvent, viz. MeOH versus EtOH, the other structural components are the same.

Structure description top

For solid-state emission behavior and intermolecular packing interactions for a closely related compound where methanol is replaced by ethanol, see: Lifshits et al. (2015). This compound and the title compound are solvatomorphs with identical space groups type and comparable lattice parameters. Except for the identity of the coordinating solvent, viz. MeOH versus EtOH, the other structural components are the same.

Synthesis and crystallization top

The title compound was prepared in an analogous manner to Zn Cbz - EtOH (Lifshits et al., 2015). Single crystals were obtained by the solvothermal reaction of 5-(9H-carbazol-9-yl)-isophthalic acid and zinc nitrate in DMF/MeOH at room temperature overnight.

Refinement details top

All H-atom positions were located from difference maps, then refined with isotropic temperature factors. Subsequently, positional restraints were added for all hydrogen atoms and Uiso values for hydrogen atoms were restrained to 1.2Ueq of the attached atom.

Computing details top

Data collection: APEX3 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ShelXle (Hübschle et al., 2011); software used to prepare material for publication: APEX3 (Bruker, 2015).

Figures top
[Figure 1] Fig. 1. Part of the title structure showing the dimetallic Zn secondary building unit with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal structure of the title complex in a projection down [001]. Colour code: light green: C, dark blue: N, red: O, white: H, yellow spheres: Zn.
[Figure 3] Fig. 3. Crystal structure of the title complex in a projection down [100] showing the layer-like arrangement of the Zn secondary building units and the carbazole moieties parallel to (001), and the interdigitation of carbazoles to form stacked layers along [010]. Colour code as in Fig. 2.
[Figure 4] Fig. 4. C—H···π interactions between carbazole moieties in the title structure.
[Figure 5] Fig. 5. C—H···O interactions between the coordinating DMF molecule, the DMF solvate molecule, and ligating carboxylate oxygen atoms.
Poly[[[µ4-5-(9H-carbazol-9-yl)isophthalato][µ3-5-(9H-carbazol-9-yl)isophthalato]bis(dimethylformamide)(methanol)dizinc] dimethylformamide monosolvate] top
Crystal data top
[Zn2(C20H11NO4)2(C3H7NO)2(CH3OH)]·C3H7NODx = 1.468 Mg m3
Mr = 1040.66Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, P212121Cell parameters from 9734 reflections
a = 10.2867 (4) Åθ = 5.4–68.3°
b = 17.0328 (7) ŵ = 1.84 mm1
c = 26.8808 (11) ÅT = 100 K
V = 4709.8 (3) Å3Prism, clear colourless
Z = 40.40 × 0.22 × 0.22 mm
F(000) = 2152
Data collection top
Bruker D8 Venture CMOS
diffractometer
8611 independent reflections
Radiation source: ImuS micro-focus source with QUAZAR optics8561 reflections with I > 2σ(I)
Mirrors monochromatorRint = 0.019
ω– and φ–scansθmax = 68.2°, θmin = 3.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
h = 1211
Tmin = 0.53, Tmax = 0.68k = 2020
41928 measured reflectionsl = 3132
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.019 w = 1/[σ2(Fo2) + (0.0221P)2 + 1.2023P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.045(Δ/σ)max = 0.004
S = 1.08Δρmax = 0.41 e Å3
8611 reflectionsΔρmin = 0.18 e Å3
629 parametersAbsolute structure: Flack x determined using 3716 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al, 2013)
546 restraintsAbsolute structure parameter: 0.005 (3)
0 constraints
Crystal data top
[Zn2(C20H11NO4)2(C3H7NO)2(CH3OH)]·C3H7NOV = 4709.8 (3) Å3
Mr = 1040.66Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 10.2867 (4) ŵ = 1.84 mm1
b = 17.0328 (7) ÅT = 100 K
c = 26.8808 (11) Å0.40 × 0.22 × 0.22 mm
Data collection top
Bruker D8 Venture CMOS
diffractometer
8611 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2015)
8561 reflections with I > 2σ(I)
Tmin = 0.53, Tmax = 0.68Rint = 0.019
41928 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.019H-atom parameters constrained
wR(F2) = 0.045Δρmax = 0.41 e Å3
S = 1.08Δρmin = 0.18 e Å3
8611 reflectionsAbsolute structure: Flack x determined using 3716 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al, 2013)
629 parametersAbsolute structure parameter: 0.005 (3)
546 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.52406 (2)0.98187 (2)0.67608 (2)0.00831 (6)
Zn20.30186 (2)1.08249 (2)0.75728 (2)0.01117 (6)
N11.01341 (16)0.86300 (9)0.51641 (6)0.0129 (3)
C10.95145 (19)0.89610 (12)0.47539 (7)0.0146 (4)
C20.9057 (2)0.97254 (13)0.46907 (8)0.0180 (4)
H20.91081.01020.49510.022*
C30.8523 (2)0.99110 (14)0.42298 (8)0.0248 (5)
H30.81921.04250.41760.03*
C40.8461 (2)0.93588 (15)0.38421 (8)0.0277 (5)
H40.81030.95060.3530.033*
C50.8915 (2)0.86053 (15)0.39113 (8)0.0247 (5)
H50.88720.82330.36480.03*
C60.9441 (2)0.83924 (13)0.43731 (8)0.0177 (4)
C70.99990 (19)0.76781 (12)0.45673 (8)0.0171 (4)
C81.0156 (2)0.69190 (13)0.43782 (8)0.0221 (4)
H80.98520.6790.40550.027*
C91.0761 (2)0.63599 (13)0.46707 (9)0.0238 (5)
H91.08630.58410.45470.029*
C101.1228 (2)0.65440 (13)0.51475 (9)0.0223 (5)
H101.16520.61510.53390.027*
C111.1076 (2)0.72951 (13)0.53442 (8)0.0178 (4)
H111.13960.74230.56660.021*
C121.04404 (19)0.78507 (12)0.50537 (7)0.0150 (4)
C131.0189 (2)0.89772 (10)0.56479 (7)0.0119 (4)
C141.13827 (19)0.91247 (11)0.58751 (7)0.0119 (4)
H141.21730.89910.57130.014*
C151.13966 (19)0.94734 (11)0.63455 (7)0.0115 (4)
C161.0238 (2)0.96674 (10)0.65848 (7)0.0113 (3)
H161.02580.99110.69030.014*
C170.90537 (19)0.95048 (11)0.63589 (7)0.0107 (4)
C180.90292 (19)0.91604 (11)0.58874 (7)0.0117 (4)
H180.82220.90520.5730.014*
C191.26733 (18)0.96743 (10)0.65857 (7)0.0112 (4)
O11.36949 (13)0.93922 (8)0.63956 (5)0.0135 (3)
O21.26507 (14)1.01114 (9)0.69596 (5)0.0166 (3)
C200.77903 (18)0.97111 (11)0.66134 (7)0.0118 (4)
O30.77960 (14)1.01396 (9)0.69850 (5)0.0174 (3)
O40.67727 (13)0.94091 (8)0.64176 (5)0.0145 (3)
N20.39399 (18)0.83315 (10)0.95005 (6)0.0147 (3)
C210.4863 (2)0.83442 (11)0.98791 (7)0.0155 (4)
C220.6179 (2)0.81631 (12)0.98552 (8)0.0188 (4)
H220.65580.79590.9560.023*
C230.6920 (3)0.82912 (12)1.02792 (8)0.0245 (5)
H230.78250.81811.02720.029*
C240.6360 (3)0.85803 (13)1.07181 (8)0.0270 (5)
H240.6890.86691.10020.032*
C250.5048 (3)0.87372 (12)1.07420 (8)0.0264 (5)
H250.46730.89191.10440.032*
C260.4265 (2)0.86281 (12)1.03187 (8)0.0190 (4)
C270.2928 (2)0.87905 (11)1.01955 (8)0.0197 (4)
C280.1854 (3)0.90598 (12)1.04676 (8)0.0265 (5)
H280.19330.9171.08130.032*
C290.0688 (3)0.91627 (14)1.02287 (10)0.0302 (5)
H290.00410.93461.04110.036*
C300.0554 (2)0.90011 (13)0.97173 (10)0.0281 (5)
H300.02640.90810.95610.034*
C310.1596 (2)0.87272 (12)0.94368 (8)0.0212 (4)
H310.15090.86170.90920.025*
C320.2771 (2)0.86227 (11)0.96842 (8)0.0167 (4)
C330.4234 (2)0.81833 (11)0.89901 (7)0.0124 (4)
C340.42478 (19)0.88080 (11)0.86558 (7)0.0121 (4)
H340.40320.93220.87650.015*
C350.45792 (18)0.86756 (11)0.81612 (7)0.0109 (4)
C360.48732 (19)0.79181 (11)0.79992 (7)0.0106 (4)
H360.51150.78290.76630.013*
C370.48112 (19)0.72937 (10)0.83313 (7)0.0107 (3)
C380.45010 (18)0.74252 (11)0.88311 (7)0.0118 (4)
H380.44740.70.90590.014*
C390.45579 (18)0.93481 (11)0.77969 (7)0.0106 (4)
O50.39906 (14)0.99586 (8)0.79345 (5)0.0146 (3)
O60.51058 (13)0.92271 (7)0.73846 (5)0.0134 (3)
C400.50276 (18)0.64683 (11)0.81456 (7)0.0107 (4)
O70.53555 (15)0.63806 (8)0.77011 (5)0.0153 (3)
O80.48208 (14)0.59232 (7)0.84533 (5)0.0131 (3)
N30.18493 (18)1.29637 (10)0.69906 (7)0.0203 (4)
C410.1585 (3)1.28253 (18)0.64698 (9)0.0359 (6)
H41A0.15851.22590.64050.043*
H41B0.22581.30780.62670.043*
H41C0.07331.30450.63840.043*
C420.1993 (3)1.37942 (14)0.71429 (12)0.0368 (6)
H42A0.22821.38180.7490.044*
H42B0.11561.40630.7110.044*
H42C0.26381.40510.6930.044*
C430.2047 (2)1.23963 (13)0.73133 (9)0.0231 (4)
H430.23041.25370.76410.028*
O90.19190 (17)1.16868 (9)0.72161 (6)0.0249 (3)
N40.23401 (18)1.14908 (10)0.90142 (6)0.0165 (4)
C440.1897 (2)1.23038 (12)0.90000 (8)0.0212 (4)
H44A0.24211.25990.8760.025*
H44B0.19911.25390.93310.025*
H44C0.09821.23190.890.025*
C450.2081 (2)1.10314 (13)0.94622 (7)0.0206 (4)
H45A0.11431.09430.94940.025*
H45B0.23961.13180.97540.025*
H45C0.25291.05250.94390.025*
C460.2883 (2)1.11725 (12)0.86199 (7)0.0170 (4)
H460.3171.06440.86440.02*
O100.30448 (16)1.15212 (8)0.82162 (5)0.0193 (3)
N50.18348 (18)0.76557 (10)0.75996 (7)0.0198 (4)
C470.1482 (2)0.70971 (13)0.79858 (9)0.0228 (5)
H47A0.14740.73630.83090.027*
H47B0.21170.66680.79920.027*
H47C0.06160.68840.79160.027*
C480.2438 (3)0.73480 (16)0.71458 (9)0.0299 (5)
H48A0.26540.77840.69230.036*
H48B0.1830.69920.69780.036*
H48C0.32320.70620.72320.036*
C490.1679 (2)0.84238 (13)0.76636 (8)0.0218 (4)
H490.19520.8760.74020.026*
O110.12041 (16)0.87346 (9)0.80389 (6)0.0238 (3)
C500.0105 (2)1.06679 (13)0.80194 (9)0.0265 (5)
H50A0.02211.12390.80270.032*
H50B0.02011.04870.83450.032*
H50C0.05361.0530.77640.032*
O120.13112 (15)1.03020 (9)0.79064 (6)0.0238 (3)
H12O0.12290.98620.79540.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.00790 (11)0.00827 (11)0.00877 (11)0.00017 (9)0.00090 (9)0.00012 (9)
Zn20.01339 (12)0.00866 (11)0.01146 (12)0.00126 (9)0.00188 (9)0.00029 (9)
N10.0120 (8)0.0150 (7)0.0118 (7)0.0003 (6)0.0004 (6)0.0050 (6)
C10.0096 (9)0.0205 (10)0.0136 (9)0.0038 (7)0.0005 (7)0.0014 (7)
C20.0167 (10)0.0191 (10)0.0184 (10)0.0045 (8)0.0014 (8)0.0004 (8)
C30.0262 (12)0.0244 (11)0.0238 (11)0.0048 (9)0.0047 (9)0.0069 (9)
C40.0296 (13)0.0364 (13)0.0172 (11)0.0084 (10)0.0071 (9)0.0048 (9)
C50.0254 (12)0.0343 (12)0.0143 (10)0.0077 (10)0.0024 (9)0.0064 (9)
C60.0140 (10)0.0240 (10)0.0149 (9)0.0051 (8)0.0017 (7)0.0052 (8)
C70.0112 (10)0.0222 (10)0.0178 (9)0.0035 (8)0.0034 (7)0.0074 (8)
C80.0193 (11)0.0234 (10)0.0236 (10)0.0057 (9)0.0057 (9)0.0122 (8)
C90.0197 (11)0.0186 (10)0.0331 (12)0.0035 (9)0.0119 (9)0.0110 (9)
C100.0139 (10)0.0188 (10)0.0342 (12)0.0015 (8)0.0079 (9)0.0025 (9)
C110.0120 (9)0.0200 (10)0.0214 (10)0.0001 (8)0.0025 (8)0.0047 (8)
C120.0103 (9)0.0174 (9)0.0174 (9)0.0020 (7)0.0042 (7)0.0055 (7)
C130.0128 (9)0.0111 (8)0.0119 (8)0.0007 (7)0.0006 (7)0.0014 (7)
C140.0100 (9)0.0117 (9)0.0140 (9)0.0002 (7)0.0009 (7)0.0005 (7)
C150.0113 (9)0.0091 (8)0.0141 (9)0.0005 (7)0.0000 (7)0.0017 (7)
C160.0138 (9)0.0095 (8)0.0106 (8)0.0002 (7)0.0010 (7)0.0008 (6)
C170.0112 (9)0.0090 (8)0.0118 (9)0.0002 (7)0.0016 (7)0.0017 (7)
C180.0092 (9)0.0107 (8)0.0152 (9)0.0007 (7)0.0014 (7)0.0009 (7)
C190.0106 (9)0.0104 (9)0.0127 (9)0.0005 (7)0.0001 (7)0.0032 (7)
O10.0084 (7)0.0156 (7)0.0166 (7)0.0000 (5)0.0013 (5)0.0023 (5)
O20.0141 (7)0.0206 (7)0.0151 (7)0.0022 (6)0.0027 (5)0.0063 (6)
C200.0109 (9)0.0104 (8)0.0140 (9)0.0015 (7)0.0021 (7)0.0032 (7)
O30.0146 (7)0.0222 (7)0.0155 (7)0.0014 (6)0.0021 (5)0.0068 (6)
O40.0099 (7)0.0173 (7)0.0163 (7)0.0003 (5)0.0016 (5)0.0037 (5)
N20.0219 (9)0.0129 (8)0.0092 (8)0.0017 (7)0.0028 (7)0.0004 (6)
C210.0284 (11)0.0080 (8)0.0100 (8)0.0010 (8)0.0010 (8)0.0009 (7)
C220.0277 (12)0.0129 (9)0.0157 (10)0.0024 (8)0.0009 (8)0.0016 (8)
C230.0364 (13)0.0148 (9)0.0221 (11)0.0026 (10)0.0090 (10)0.0031 (8)
C240.0468 (15)0.0184 (10)0.0159 (10)0.0035 (10)0.0105 (10)0.0022 (8)
C250.0545 (17)0.0136 (9)0.0110 (9)0.0080 (10)0.0022 (10)0.0012 (7)
C260.0357 (12)0.0091 (9)0.0122 (9)0.0044 (8)0.0049 (8)0.0001 (7)
C270.0348 (12)0.0099 (9)0.0145 (9)0.0059 (9)0.0092 (9)0.0029 (7)
C280.0403 (14)0.0167 (10)0.0226 (11)0.0058 (10)0.0180 (10)0.0065 (8)
C290.0340 (13)0.0191 (10)0.0376 (13)0.0027 (10)0.0224 (11)0.0056 (10)
C300.0239 (12)0.0215 (11)0.0388 (13)0.0007 (9)0.0104 (10)0.0011 (10)
C310.0243 (11)0.0159 (10)0.0233 (11)0.0007 (8)0.0063 (9)0.0007 (8)
C320.0251 (11)0.0085 (8)0.0165 (10)0.0006 (8)0.0090 (8)0.0009 (7)
C330.0147 (9)0.0145 (9)0.0079 (8)0.0004 (8)0.0004 (7)0.0019 (7)
C340.0130 (9)0.0104 (9)0.0131 (9)0.0005 (7)0.0009 (7)0.0013 (7)
C350.0099 (9)0.0112 (8)0.0117 (9)0.0000 (7)0.0011 (7)0.0009 (7)
C360.0095 (9)0.0133 (8)0.0091 (8)0.0007 (7)0.0007 (7)0.0009 (7)
C370.0088 (8)0.0113 (8)0.0119 (8)0.0009 (7)0.0009 (7)0.0007 (7)
C380.0117 (9)0.0117 (9)0.0119 (9)0.0007 (7)0.0007 (7)0.0022 (7)
C390.0098 (9)0.0110 (9)0.0110 (8)0.0005 (7)0.0022 (7)0.0007 (7)
O50.0215 (7)0.0096 (6)0.0127 (6)0.0037 (5)0.0014 (5)0.0006 (5)
O60.0155 (7)0.0140 (6)0.0106 (6)0.0024 (5)0.0033 (5)0.0030 (5)
C400.0085 (9)0.0117 (8)0.0120 (9)0.0009 (7)0.0018 (7)0.0006 (7)
O70.0211 (7)0.0141 (6)0.0107 (6)0.0067 (6)0.0010 (6)0.0020 (5)
O80.0160 (7)0.0097 (6)0.0136 (6)0.0005 (5)0.0011 (5)0.0010 (5)
N30.0154 (9)0.0186 (8)0.0270 (9)0.0020 (7)0.0017 (7)0.0010 (7)
C410.0376 (15)0.0446 (15)0.0256 (12)0.0053 (12)0.0028 (10)0.0056 (11)
C420.0266 (13)0.0203 (11)0.0634 (18)0.0022 (10)0.0086 (13)0.0019 (11)
C430.0193 (10)0.0224 (10)0.0276 (11)0.0038 (9)0.0044 (9)0.0020 (9)
O90.0241 (8)0.0159 (7)0.0349 (8)0.0039 (6)0.0082 (7)0.0007 (6)
N40.0170 (9)0.0172 (8)0.0152 (8)0.0004 (7)0.0013 (7)0.0041 (7)
C440.0235 (11)0.0173 (10)0.0229 (10)0.0020 (9)0.0041 (9)0.0065 (8)
C450.0227 (11)0.0245 (10)0.0146 (10)0.0006 (9)0.0028 (8)0.0007 (8)
C460.0201 (10)0.0151 (9)0.0156 (10)0.0021 (8)0.0006 (8)0.0024 (7)
O100.0295 (8)0.0143 (6)0.0142 (6)0.0018 (6)0.0048 (7)0.0035 (5)
N50.0182 (9)0.0209 (8)0.0202 (8)0.0020 (7)0.0010 (7)0.0009 (7)
C470.0216 (11)0.0207 (10)0.0260 (11)0.0009 (9)0.0006 (9)0.0025 (9)
C480.0301 (13)0.0351 (13)0.0247 (12)0.0039 (11)0.0027 (10)0.0041 (10)
C490.0163 (10)0.0234 (10)0.0257 (11)0.0037 (8)0.0019 (8)0.0057 (9)
O110.0189 (8)0.0186 (7)0.0339 (9)0.0006 (6)0.0013 (7)0.0009 (6)
C500.0168 (11)0.0255 (11)0.0374 (12)0.0029 (9)0.0072 (9)0.0048 (9)
O120.0192 (8)0.0142 (7)0.0381 (9)0.0015 (6)0.0150 (7)0.0019 (6)
Geometric parameters (Å, º) top
Zn1—O41.9548 (14)C27—C281.402 (3)
Zn1—O61.9614 (13)C27—C321.413 (3)
Zn1—O8i1.9683 (13)C28—C291.372 (4)
Zn1—O1ii2.0047 (14)C28—H280.95
Zn2—O52.0303 (14)C29—C301.409 (4)
Zn2—O7i2.0580 (14)C29—H290.95
Zn2—O2ii2.0826 (14)C30—C311.391 (3)
Zn2—O92.0867 (15)C30—H300.95
Zn2—O102.0974 (14)C31—C321.391 (3)
Zn2—O122.1638 (15)C31—H310.95
N1—C11.393 (3)C33—C381.388 (3)
N1—C121.396 (3)C33—C341.393 (3)
N1—C131.430 (2)C34—C351.391 (3)
C1—C21.395 (3)C34—H340.95
C1—C61.411 (3)C35—C361.395 (3)
C2—C31.392 (3)C35—C391.507 (3)
C2—H20.95C36—C371.390 (3)
C3—C41.405 (3)C36—H360.95
C3—H30.95C37—C381.399 (3)
C4—C51.378 (4)C37—C401.508 (2)
C4—H40.95C38—H380.95
C5—C61.402 (3)C39—O51.248 (2)
C5—H50.95C39—O61.260 (2)
C6—C71.443 (3)C40—O71.250 (2)
C7—C81.399 (3)C40—O81.262 (2)
C7—C121.415 (3)O7—Zn2iv2.0580 (14)
C8—C91.383 (4)O8—Zn1iv1.9683 (13)
C8—H80.95N3—C431.315 (3)
C9—C101.404 (3)N3—C411.445 (3)
C9—H90.95N3—C421.480 (3)
C10—C111.393 (3)C41—H41A0.98
C10—H100.95C41—H41B0.98
C11—C121.390 (3)C41—H41C0.98
C11—H110.95C42—H42A0.98
C13—C181.391 (3)C42—H42B0.98
C13—C141.395 (3)C42—H42C0.98
C14—C151.397 (3)C43—O91.243 (3)
C14—H140.95C43—H430.95
C15—C161.395 (3)N4—C461.315 (3)
C15—C191.503 (3)N4—C441.458 (3)
C16—C171.389 (3)N4—C451.461 (3)
C16—H160.95C44—H44A0.98
C17—C181.397 (3)C44—H44B0.98
C17—C201.510 (3)C44—H44C0.98
C18—H180.95C45—H45A0.98
C19—O21.251 (2)C45—H45B0.98
C19—O11.263 (2)C45—H45C0.98
O1—Zn1iii2.0047 (14)C46—O101.248 (3)
O2—Zn2iii2.0825 (14)C46—H460.95
C20—O31.237 (2)N5—C491.329 (3)
C20—O41.279 (2)N5—C471.454 (3)
N2—C321.391 (3)N5—C481.465 (3)
N2—C211.392 (3)C47—H47A0.98
N2—C331.427 (2)C47—H47B0.98
C21—C221.390 (3)C47—H47C0.98
C21—C261.417 (3)C48—H48A0.98
C22—C231.388 (3)C48—H48B0.98
C22—H220.95C48—H48C0.98
C23—C241.402 (4)C49—O111.240 (3)
C23—H230.95C49—H490.95
C24—C251.377 (4)C50—O121.421 (3)
C24—H240.95C50—H50A0.98
C25—C261.406 (3)C50—H50B0.98
C25—H250.95C50—H50C0.98
C26—C271.442 (4)O12—H12O0.7642
O4—Zn1—O6106.09 (6)C32—C27—C26107.09 (19)
O4—Zn1—O8i103.24 (6)C29—C28—C27119.1 (2)
O6—Zn1—O8i137.62 (5)C29—C28—H28120.4
O4—Zn1—O1ii106.21 (5)C27—C28—H28120.4
O6—Zn1—O1ii100.16 (6)C28—C29—C30121.2 (2)
O8i—Zn1—O1ii100.24 (6)C28—C29—H29119.4
O5—Zn2—O7i96.05 (6)C30—C29—H29119.4
O5—Zn2—O2ii92.55 (6)C31—C30—C29121.3 (2)
O7i—Zn2—O2ii97.64 (5)C31—C30—H30119.4
O5—Zn2—O9176.68 (7)C29—C30—H30119.4
O7i—Zn2—O987.28 (6)C30—C31—C32116.9 (2)
O2ii—Zn2—O987.04 (6)C30—C31—H31121.5
O5—Zn2—O1090.56 (6)C32—C31—H31121.5
O7i—Zn2—O1091.40 (6)C31—C32—N2128.81 (18)
O2ii—Zn2—O10170.07 (6)C31—C32—C27122.6 (2)
O9—Zn2—O1089.32 (6)N2—C32—C27108.6 (2)
O5—Zn2—O1284.38 (6)C38—C33—C34120.68 (17)
O7i—Zn2—O12175.73 (6)C38—C33—N2120.16 (17)
O2ii—Zn2—O1286.58 (6)C34—C33—N2119.16 (17)
O9—Zn2—O1292.30 (7)C35—C34—C33119.69 (17)
O10—Zn2—O1284.34 (6)C35—C34—H34120.2
C1—N1—C12108.65 (16)C33—C34—H34120.2
C1—N1—C13124.80 (16)C34—C35—C36120.11 (17)
C12—N1—C13125.29 (16)C34—C35—C39119.62 (17)
N1—C1—C2128.95 (18)C36—C35—C39120.21 (16)
N1—C1—C6108.73 (18)C37—C36—C35119.81 (16)
C2—C1—C6122.29 (19)C37—C36—H36120.1
C3—C2—C1117.0 (2)C35—C36—H36120.1
C3—C2—H2121.5C36—C37—C38120.32 (16)
C1—C2—H2121.5C36—C37—C40119.59 (16)
C2—C3—C4121.7 (2)C38—C37—C40120.05 (16)
C2—C3—H3119.1C33—C38—C37119.33 (17)
C4—C3—H3119.1C33—C38—H38120.3
C5—C4—C3120.5 (2)C37—C38—H38120.3
C5—C4—H4119.7O5—C39—O6127.29 (17)
C3—C4—H4119.7O5—C39—C35116.57 (16)
C4—C5—C6119.4 (2)O6—C39—C35116.14 (16)
C4—C5—H5120.3C39—O5—Zn2133.92 (12)
C6—C5—H5120.3C39—O6—Zn1134.38 (12)
C5—C6—C1119.1 (2)O7—C40—O8125.74 (17)
C5—C6—C7133.8 (2)O7—C40—C37117.86 (16)
C1—C6—C7107.15 (18)O8—C40—C37116.36 (15)
C8—C7—C12119.4 (2)C40—O7—Zn2iv128.02 (12)
C8—C7—C6133.9 (2)C40—O8—Zn1iv121.14 (12)
C12—C7—C6106.67 (17)C43—N3—C41123.3 (2)
C9—C8—C7118.8 (2)C43—N3—C42120.3 (2)
C9—C8—H8120.6C41—N3—C42116.3 (2)
C7—C8—H8120.6N3—C41—H41A109.5
C8—C9—C10121.3 (2)N3—C41—H41B109.5
C8—C9—H9119.4H41A—C41—H41B109.5
C10—C9—H9119.4N3—C41—H41C109.5
C11—C10—C9120.9 (2)H41A—C41—H41C109.5
C11—C10—H10119.6H41B—C41—H41C109.5
C9—C10—H10119.6N3—C42—H42A109.5
C12—C11—C10117.7 (2)N3—C42—H42B109.5
C12—C11—H11121.2H42A—C42—H42B109.5
C10—C11—H11121.2N3—C42—H42C109.5
C11—C12—N1129.34 (18)H42A—C42—H42C109.5
C11—C12—C7121.91 (19)H42B—C42—H42C109.5
N1—C12—C7108.75 (18)O9—C43—N3124.0 (2)
C18—C13—C14120.81 (16)O9—C43—H43118.0
C18—C13—N1118.69 (17)N3—C43—H43118.0
C14—C13—N1120.50 (18)C43—O9—Zn2121.99 (15)
C13—C14—C15118.82 (18)C46—N4—C44120.20 (18)
C13—C14—H14120.6C46—N4—C45121.41 (17)
C15—C14—H14120.6C44—N4—C45118.25 (17)
C16—C15—C14120.63 (18)N4—C44—H44A109.5
C16—C15—C19119.67 (17)N4—C44—H44B109.5
C14—C15—C19119.64 (17)H44A—C44—H44B109.5
C17—C16—C15120.06 (17)N4—C44—H44C109.5
C17—C16—H16120.0H44A—C44—H44C109.5
C15—C16—H16120.0H44B—C44—H44C109.5
C16—C17—C18119.76 (18)N4—C45—H45A109.5
C16—C17—C20120.68 (16)N4—C45—H45B109.5
C18—C17—C20119.55 (17)H45A—C45—H45B109.5
C13—C18—C17119.91 (17)N4—C45—H45C109.5
C13—C18—H18120.0H45A—C45—H45C109.5
C17—C18—H18120.0H45B—C45—H45C109.5
O2—C19—O1124.52 (17)O10—C46—N4124.13 (19)
O2—C19—C15117.67 (17)O10—C46—H46117.9
O1—C19—C15117.81 (16)N4—C46—H46117.9
C19—O1—Zn1iii108.90 (12)C46—O10—Zn2116.49 (12)
C19—O2—Zn2iii168.46 (13)C49—N5—C47121.42 (19)
O3—C20—O4124.97 (17)C49—N5—C48120.73 (19)
O3—C20—C17119.93 (17)C47—N5—C48117.77 (18)
O4—C20—C17115.10 (16)N5—C47—H47A109.5
C20—O4—Zn1108.79 (12)N5—C47—H47B109.5
C32—N2—C21108.95 (16)H47A—C47—H47B109.5
C32—N2—C33125.96 (17)N5—C47—H47C109.5
C21—N2—C33124.11 (18)H47A—C47—H47C109.5
C22—C21—N2128.86 (18)H47B—C47—H47C109.5
C22—C21—C26122.47 (19)N5—C48—H48A109.5
N2—C21—C26108.58 (19)N5—C48—H48B109.5
C23—C22—C21117.5 (2)H48A—C48—H48B109.5
C23—C22—H22121.2N5—C48—H48C109.5
C21—C22—H22121.2H48A—C48—H48C109.5
C22—C23—C24121.3 (2)H48B—C48—H48C109.5
C22—C23—H23119.3O11—C49—N5125.0 (2)
C24—C23—H23119.3O11—C49—H49117.5
C25—C24—C23120.7 (2)N5—C49—H49117.5
C25—C24—H24119.7O12—C50—H50A109.5
C23—C24—H24119.7O12—C50—H50B109.5
C24—C25—C26119.8 (2)H50A—C50—H50B109.5
C24—C25—H25120.1O12—C50—H50C109.5
C26—C25—H25120.1H50A—C50—H50C109.5
C25—C26—C21118.1 (2)H50B—C50—H50C109.5
C25—C26—C27135.0 (2)C50—O12—Zn2128.06 (13)
C21—C26—C27106.75 (18)C50—O12—H12O107.3
C28—C27—C32118.9 (2)Zn2—O12—H12O124.2
C28—C27—C26134.0 (2)
C12—N1—C1—C2178.7 (2)C26—C21—C22—C231.8 (3)
C13—N1—C1—C213.6 (3)C21—C22—C23—C241.0 (3)
C12—N1—C1—C61.0 (2)C22—C23—C24—C250.8 (3)
C13—N1—C1—C6168.66 (18)C23—C24—C25—C261.8 (3)
N1—C1—C2—C3177.2 (2)C24—C25—C26—C211.0 (3)
C6—C1—C2—C30.4 (3)C24—C25—C26—C27173.6 (2)
C1—C2—C3—C40.8 (3)C22—C21—C26—C250.8 (3)
C2—C3—C4—C51.0 (4)N2—C21—C26—C25175.98 (17)
C3—C4—C5—C60.0 (4)C22—C21—C26—C27176.83 (18)
C4—C5—C6—C11.2 (3)N2—C21—C26—C270.0 (2)
C4—C5—C6—C7179.4 (2)C25—C26—C27—C286.7 (4)
N1—C1—C6—C5176.59 (19)C21—C26—C27—C28178.2 (2)
C2—C1—C6—C51.4 (3)C25—C26—C27—C32173.3 (2)
N1—C1—C6—C72.1 (2)C21—C26—C27—C321.7 (2)
C2—C1—C6—C7179.99 (18)C32—C27—C28—C290.9 (3)
C5—C6—C7—C84.4 (4)C26—C27—C28—C29179.2 (2)
C1—C6—C7—C8177.2 (2)C27—C28—C29—C300.1 (3)
C5—C6—C7—C12176.0 (2)C28—C29—C30—C310.4 (4)
C1—C6—C7—C122.4 (2)C29—C30—C31—C320.1 (3)
C12—C7—C8—C91.1 (3)C30—C31—C32—N2177.3 (2)
C6—C7—C8—C9179.4 (2)C30—C31—C32—C270.7 (3)
C7—C8—C9—C100.7 (3)C21—N2—C32—C31179.0 (2)
C8—C9—C10—C111.0 (3)C33—N2—C32—C3110.0 (3)
C9—C10—C11—C120.5 (3)C21—N2—C32—C272.8 (2)
C10—C11—C12—N1178.3 (2)C33—N2—C32—C27171.78 (18)
C10—C11—C12—C72.3 (3)C28—C27—C32—C311.2 (3)
C1—N1—C12—C11178.9 (2)C26—C27—C32—C31178.88 (19)
C13—N1—C12—C1113.4 (3)C28—C27—C32—N2177.18 (18)
C1—N1—C12—C70.6 (2)C26—C27—C32—N22.8 (2)
C13—N1—C12—C7167.07 (18)C32—N2—C33—C38117.0 (2)
C8—C7—C12—C112.6 (3)C21—N2—C33—C3875.7 (3)
C6—C7—C12—C11177.73 (19)C32—N2—C33—C3463.0 (3)
C8—C7—C12—N1177.81 (18)C21—N2—C33—C34104.4 (2)
C6—C7—C12—N11.8 (2)C38—C33—C34—C352.4 (3)
C1—N1—C13—C1857.1 (3)N2—C33—C34—C35177.66 (18)
C12—N1—C13—C18108.6 (2)C33—C34—C35—C361.1 (3)
C1—N1—C13—C14123.2 (2)C33—C34—C35—C39178.31 (17)
C12—N1—C13—C1471.1 (3)C34—C35—C36—C371.2 (3)
C18—C13—C14—C151.1 (3)C39—C35—C36—C37175.98 (17)
N1—C13—C14—C15179.23 (17)C35—C36—C37—C382.3 (3)
C13—C14—C15—C160.3 (3)C35—C36—C37—C40175.25 (17)
C13—C14—C15—C19176.94 (17)C34—C33—C38—C371.2 (3)
C14—C15—C16—C170.9 (3)N2—C33—C38—C37178.79 (18)
C19—C15—C16—C17178.11 (17)C36—C37—C38—C331.1 (3)
C15—C16—C17—C181.2 (3)C40—C37—C38—C33176.43 (17)
C15—C16—C17—C20179.98 (17)C34—C35—C39—O514.1 (3)
C14—C13—C18—C170.7 (3)C36—C35—C39—O5163.01 (18)
N1—C13—C18—C17179.58 (17)C34—C35—C39—O6166.52 (18)
C16—C17—C18—C130.4 (3)C36—C35—C39—O616.3 (3)
C20—C17—C18—C13179.24 (17)O6—C39—O5—Zn228.8 (3)
C16—C15—C19—O210.1 (3)C35—C39—O5—Zn2150.43 (14)
C14—C15—C19—O2167.10 (17)O5—C39—O6—Zn16.2 (3)
C16—C15—C19—O1170.02 (17)C35—C39—O6—Zn1173.02 (12)
C14—C15—C19—O112.7 (3)C36—C37—C40—O75.3 (3)
O2—C19—O1—Zn1iii3.8 (2)C38—C37—C40—O7177.10 (17)
C15—C19—O1—Zn1iii175.98 (13)C36—C37—C40—O8172.62 (17)
O1—C19—O2—Zn2iii3.9 (8)C38—C37—C40—O84.9 (3)
C15—C19—O2—Zn2iii175.9 (6)O8—C40—O7—Zn2iv59.3 (3)
C16—C17—C20—O311.8 (3)C37—C40—O7—Zn2iv122.99 (16)
C18—C17—C20—O3166.93 (17)O7—C40—O8—Zn1iv8.6 (3)
C16—C17—C20—O4167.72 (17)C37—C40—O8—Zn1iv169.16 (12)
C18—C17—C20—O413.5 (2)C41—N3—C43—O96.4 (4)
O3—C20—O4—Zn15.5 (2)C42—N3—C43—O9178.5 (2)
C17—C20—O4—Zn1174.97 (12)N3—C43—O9—Zn2149.88 (19)
C32—N2—C21—C22174.83 (19)C44—N4—C46—O100.8 (3)
C33—N2—C21—C225.6 (3)C45—N4—C46—O10174.8 (2)
C32—N2—C21—C261.7 (2)N4—C46—O10—Zn2150.09 (18)
C33—N2—C21—C26170.93 (17)C47—N5—C49—O111.9 (3)
N2—C21—C22—C23174.29 (19)C48—N5—C49—O11178.5 (2)
Symmetry codes: (i) x+1, y+1/2, z+3/2; (ii) x1, y, z; (iii) x+1, y, z; (iv) x+1, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg3, Cg4 and Cg6 are the centroids of the N1/C1/C6/C7/C12, C1–C6, C7–C12 and C21–C26 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O12—H12O···O110.761.932.696 (2)174
C42—H42B···O11v0.982.523.327 (3)139
C43—H43···O100.952.443.028 (3)120
C46—H46···O50.952.392.995 (2)121
C47—H47B···O3iv0.982.613.417 (3)140
C47—H47C···O9vi0.982.653.608 (3)165
C2—H2···Cg6vii0.952.643.517 (2)153
C10—H10···Cg3viii0.952.643.418 (2)139
C44—H44B···Cg4ix0.982.913.596 (2)128
C45—H45B···Cg1ix0.982.853.411 (2)117
Symmetry codes: (iv) x+1, y1/2, z+3/2; (v) x, y+1/2, z+3/2; (vi) x, y1/2, z+3/2; (vii) x+3/2, y+2, z1/2; (viii) x+1/2, y+3/2, z+1; (ix) x+3/2, y+2, z+1/2.
Hydrogen-bond geometry (Å, º) top
Cg1, Cg3, Cg4 and Cg6 are the centroids of the N1/C1/C6/C7/C12, C1–C6, C7–C12 and C21–C26 rings, respectively.
D—H···AD—HH···AD···AD—H···A
O12—H12O···O110.761.932.696 (2)173.7
C42—H42B···O11i0.982.523.327 (3)139.2
C43—H43···O100.952.443.028 (3)119.7
C46—H46···O50.952.392.995 (2)121.3
C47—H47B···O3ii0.982.613.417 (3)140.1
C47—H47C···O9iii0.982.653.608 (3)165.0
C2—H2···Cg6iv0.952.643.517 (2)153
C10—H10···Cg3v0.952.643.418 (2)139
C44—H44B···Cg4vi0.982.913.596 (2)128
C45—H45B···Cg1vi0.982.853.411 (2)117
Symmetry codes: (i) x, y+1/2, z+3/2; (ii) x+1, y1/2, z+3/2; (iii) x, y1/2, z+3/2; (iv) x+3/2, y+2, z1/2; (v) x+1/2, y+3/2, z+1; (vi) x+3/2, y+2, z+1/2.
 

Acknowledgements

This work was supported by Bowling Green State University and the BGSU Building Strength program.

References

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