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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1452.
Published online 2008 July 9. doi:  10.1107/S1600536808020746
PMCID: PMC2962083

N′-(3,5-Di-tert-butyl-4-hydroxy­benzyl­idene)-2-hydroxy­benzohydrazide methanol solvate

Abstract

The asymmetric unit of the title compound, C22H28N2O3·CH4O, consists of two independent Schiff base mol­ecules and two independent methanol solvent mol­ecules. In one Schiff base mol­ecule, the 2-hydr­oxy group forms an intra­molecular hydrogen bond with the amide O atom, whereas in the other Schiff base mol­ecule, the 2-hydr­oxy-substituted benzene ring is oriented so that the 2-hydr­oxy group serves as hydrogen-bond acceptor for the amide NH group. In the crystal structure, Schiff base mol­ecules inter­act with methanol solvent to furnish a hydrogen-bonded chain.

Related literature

For references to other crystal structures of substituted benzyl­idene-2-hydroxy­benzohydrazides, see: Yehye et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1452-scheme1.jpg

Experimental

Crystal data

  • C22H28N2O3·CH4O
  • M r = 400.51
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1452-efi1.jpg
  • a = 24.184 (4) Å
  • b = 11.198 (2) Å
  • c = 33.112 (5) Å
  • β = 96.389 (3)°
  • V = 8911 (2) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 100 (2) K
  • 0.35 × 0.20 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 22590 measured reflections
  • 7825 independent reflections
  • 4711 reflections with I > 2σ(I)
  • R int = 0.090

Refinement

  • R[F 2 > 2σ(F 2)] = 0.074
  • wR(F 2) = 0.239
  • S = 1.09
  • 7825 reflections
  • 529 parameters
  • H-atom parameters constrained
  • Δρmax = 0.74 e Å−3
  • Δρmin = −0.58 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020746/lh2656sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020746/lh2656Isup2.hkl

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

Acknowledgments

The authors acknowledge th SAGA grant (No. 06-02-03-0147) for supporting this study, and the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

The crystal structures of a number of substituted benzylidene-2-hydroxybenzohydrazides have been reported, along with that of the 2,4-dimethoxy derivative, which crystallizes as an ethanol solvate (Yehye et al., 2008 and references cited within). In the title compound , the asymmetric unit consists of two Schiff-base and two solvent molecules. In one Schiff base molecule, the hydroxy group forms an intramolecular hydrogen bond with the amido C=O oxygen atom whereas in the other Schiff base molecule, the phenylene ring is rotated so that the 2-hydroxy group now serves as hydrogen-bond acceptor to the amido NH nitrogen atom (Fig. 1). The Schiff-base molecules interact with the two lattice methanol molecules to furnish a hydrogen-bonded chain.

Experimental

2-Hydroxybenzohydrazide (0.5 g, 4 mmol) and 3,5-di-tert-butyl-4-hydroxybenzaldehyde (0.9 g, 4 mmol) were heated in ethanol (30 ml) for 2 h. The solvent was removed by evaporation and the product recrystallized from methanol.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5 U(C).

The oxygen- and nitrogen-bound H-atoms were similarly treated as riding (O–H 0.84 Å, N–H 0.88 Å).

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C21H26N2O3.CH3OH at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radiius.

Crystal data

C22H28N2O3·CH4OF000 = 3456
Mr = 400.51Dx = 1.194 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2005 reflections
a = 24.184 (4) Åθ = 2.3–19.8º
b = 11.198 (2) ŵ = 0.08 mm1
c = 33.112 (5) ÅT = 100 (2) K
β = 96.389 (3)ºBlock, colorless
V = 8911 (2) Å30.35 × 0.20 × 0.15 mm
Z = 16

Data collection

Bruker SMART APEX diffractometer4711 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.091
Monochromator: graphiteθmax = 27.5º
T = 100(2) Kθmin = 1.2º
ω scansh = −29→31
Absorption correction: nonek = −14→14
22590 measured reflectionsl = −37→43
7825 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.074H-atom parameters constrained
wR(F2) = 0.239  w = 1/[σ2(Fo2) + (0.1232P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
7825 reflectionsΔρmax = 0.74 e Å3
529 parametersΔρmin = −0.58 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.41029 (12)0.4254 (2)0.44485 (9)0.0356 (7)
H1O0.38710.42000.42410.053*
O20.34515 (11)0.3243 (2)0.39032 (8)0.0342 (7)
O30.11317 (11)0.0188 (2)0.20608 (8)0.0353 (7)
H3O0.07850.02100.20010.053*
O40.22728 (12)0.6204 (2)0.44067 (10)0.0429 (8)
H4O0.21220.55280.43900.064*
O50.26877 (11)0.9807 (2)0.44825 (8)0.0294 (6)
O60.57906 (11)0.8192 (2)0.34770 (9)0.0386 (7)
H6O0.58390.81500.32300.058*
O70.23156 (15)0.3840 (3)0.35578 (11)0.0607 (10)
H7O0.25580.33100.35400.091*
O80.19213 (18)0.4046 (3)0.42874 (13)0.0748 (12)
H8O0.19110.37520.40530.112*
N10.31735 (12)0.1345 (2)0.39729 (9)0.0227 (7)
H1N0.32060.06650.41070.027*
N20.27940 (12)0.1464 (3)0.36298 (9)0.0231 (7)
N30.29514 (12)0.7952 (3)0.43174 (9)0.0238 (7)
H3N0.28740.71840.43100.029*
N40.34361 (12)0.8351 (2)0.41793 (9)0.0225 (7)
C10.41722 (15)0.3175 (3)0.46271 (12)0.0259 (9)
C20.45363 (16)0.3079 (3)0.49784 (12)0.0307 (9)
H20.47230.37700.50900.037*
C30.46304 (15)0.1999 (3)0.51663 (12)0.0304 (9)
H30.48780.19480.54090.036*
C40.43671 (16)0.0973 (3)0.50049 (11)0.0294 (9)
H40.44430.02220.51320.035*
C50.39967 (15)0.1052 (3)0.46608 (11)0.0269 (9)
H50.38140.03530.45520.032*
C60.38847 (15)0.2155 (3)0.44670 (11)0.0212 (8)
C70.34899 (15)0.2288 (3)0.40966 (11)0.0244 (8)
C80.25488 (15)0.0499 (3)0.35060 (11)0.0219 (8)
H80.2634−0.02170.36540.026*
C90.21440 (14)0.0456 (3)0.31464 (11)0.0221 (8)
C100.19724 (14)0.1480 (3)0.29246 (11)0.0233 (8)
H100.20970.22410.30240.028*
C110.16278 (15)0.1412 (3)0.25655 (11)0.0247 (8)
C120.14477 (15)0.0285 (3)0.24271 (11)0.0266 (9)
C130.15856 (14)−0.0763 (3)0.26509 (11)0.0231 (8)
C140.19380 (14)−0.0637 (3)0.30063 (11)0.0224 (8)
H140.2043−0.13310.31610.027*
C150.14478 (16)0.2559 (3)0.23255 (12)0.0304 (9)
C160.16803 (18)0.3676 (3)0.25461 (13)0.0392 (11)
H16A0.20870.36310.25850.059*
H16B0.15380.37310.28110.059*
H16C0.15650.43830.23840.059*
C170.16714 (17)0.2539 (4)0.19088 (12)0.0355 (10)
H17A0.20770.24600.19470.053*
H17B0.15690.32830.17640.053*
H17C0.15100.18600.17500.053*
C180.08109 (17)0.2675 (4)0.22733 (13)0.0438 (11)
H18A0.06740.26840.25410.066*
H18B0.06480.19960.21160.066*
H18C0.07040.34200.21300.066*
C190.13496 (15)−0.1998 (3)0.25148 (12)0.0264 (9)
C200.15632 (18)−0.2376 (4)0.21133 (13)0.0435 (11)
H20A0.1971−0.23850.21480.065*
H20B0.1431−0.18070.18990.065*
H20C0.1424−0.31760.20380.065*
C210.15297 (17)−0.2956 (3)0.28285 (13)0.0360 (10)
H21A0.1937−0.30010.28680.054*
H21B0.1377−0.37290.27330.054*
H21C0.1391−0.27540.30870.054*
C220.07069 (15)−0.1977 (3)0.24675 (12)0.0300 (9)
H22A0.0564−0.27660.23820.045*
H22B0.0572−0.13820.22630.045*
H22C0.0576−0.17680.27280.045*
C230.19310 (15)0.6993 (3)0.45657 (11)0.0242 (8)
C240.14403 (15)0.6612 (3)0.46956 (11)0.0273 (9)
H240.13450.57900.46770.033*
C250.10856 (16)0.7406 (4)0.48518 (12)0.0321 (9)
H250.07430.71320.49330.038*
C260.12249 (16)0.8591 (4)0.48915 (12)0.0317 (9)
H260.09820.91340.50040.038*
C270.17232 (15)0.8997 (3)0.47672 (11)0.0260 (9)
H270.18200.98170.47970.031*
C280.20813 (15)0.8210 (3)0.45986 (11)0.0234 (8)
C290.25946 (15)0.8724 (3)0.44643 (10)0.0234 (8)
C300.37778 (15)0.7511 (3)0.41175 (10)0.0239 (8)
H300.36830.67150.41820.029*
C310.43033 (14)0.7719 (3)0.39532 (10)0.0211 (8)
C320.44696 (14)0.8847 (3)0.38361 (10)0.0224 (8)
H320.42340.95130.38660.027*
C330.49662 (14)0.9020 (3)0.36783 (10)0.0230 (8)
C340.53000 (15)0.8001 (3)0.36417 (11)0.0246 (8)
C350.51542 (15)0.6862 (3)0.37589 (11)0.0245 (8)
C360.46473 (15)0.6753 (3)0.39136 (11)0.0239 (8)
H360.45330.59870.39950.029*
C370.51376 (15)1.0271 (3)0.35460 (11)0.0273 (9)
C380.47007 (19)1.1200 (3)0.36147 (14)0.0432 (12)
H38A0.48231.19850.35280.065*
H38B0.46491.12270.39040.065*
H38C0.43481.09890.34560.065*
C390.56875 (19)1.0644 (4)0.37960 (15)0.0524 (13)
H39A0.57961.14400.37110.079*
H39B0.59801.00690.37510.079*
H39C0.56361.06590.40850.079*
C400.52080 (17)1.0296 (3)0.30912 (12)0.0343 (10)
H40A0.53191.11000.30150.051*
H40B0.48551.00830.29330.051*
H40C0.54950.97220.30350.051*
C410.55184 (16)0.5756 (3)0.37138 (12)0.0329 (10)
C420.60992 (17)0.5924 (4)0.39523 (13)0.0435 (11)
H42A0.60590.60710.42390.065*
H42B0.62860.66070.38410.065*
H42C0.63220.52010.39280.065*
C430.55643 (18)0.5518 (4)0.32594 (13)0.0442 (11)
H43A0.51910.54040.31160.066*
H43B0.57870.47970.32320.066*
H43C0.57440.62010.31430.066*
C440.52758 (19)0.4641 (3)0.38890 (16)0.0502 (13)
H44A0.49050.44870.37470.075*
H44B0.52470.47610.41790.075*
H44C0.55190.39580.38530.075*
C450.2538 (2)0.4987 (4)0.34603 (17)0.0684 (16)
H45A0.22500.55990.34670.103*
H45B0.26600.49570.31880.103*
H45C0.28550.51840.36600.103*
C460.2127 (4)0.3167 (6)0.4583 (2)0.123 (3)
H46A0.24610.34740.47450.185*
H46B0.22190.24330.44440.185*
H46C0.18410.29950.47630.185*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0406 (18)0.0229 (14)0.0412 (18)−0.0045 (12)−0.0040 (13)0.0005 (13)
O20.0429 (18)0.0181 (14)0.0379 (17)−0.0037 (12)−0.0116 (13)0.0051 (12)
O30.0337 (17)0.0385 (16)0.0287 (16)−0.0108 (12)−0.0179 (12)0.0070 (13)
O40.0356 (18)0.0349 (16)0.061 (2)−0.0053 (13)0.0162 (15)−0.0083 (16)
O50.0300 (16)0.0244 (14)0.0346 (16)−0.0022 (11)0.0070 (12)0.0019 (12)
O60.0275 (16)0.0450 (17)0.0456 (18)0.0027 (13)0.0147 (13)0.0094 (14)
O70.077 (3)0.0436 (19)0.056 (2)0.0226 (17)−0.0180 (19)−0.0070 (17)
O80.080 (3)0.046 (2)0.102 (3)−0.0073 (19)0.029 (3)−0.001 (2)
N10.0246 (17)0.0208 (16)0.0208 (16)−0.0034 (13)−0.0066 (13)0.0035 (13)
N20.0212 (17)0.0249 (16)0.0213 (16)−0.0027 (13)−0.0057 (13)0.0034 (14)
N30.0200 (17)0.0213 (16)0.0303 (18)−0.0023 (13)0.0042 (14)0.0023 (14)
N40.0185 (16)0.0253 (16)0.0238 (17)−0.0022 (13)0.0027 (13)0.0013 (14)
C10.022 (2)0.026 (2)0.030 (2)−0.0014 (16)0.0063 (17)−0.0043 (17)
C20.029 (2)0.033 (2)0.029 (2)−0.0069 (18)0.0001 (18)−0.0107 (18)
C30.021 (2)0.043 (2)0.026 (2)−0.0047 (18)−0.0007 (17)−0.0019 (19)
C40.029 (2)0.032 (2)0.026 (2)−0.0021 (17)−0.0017 (17)0.0058 (18)
C50.027 (2)0.0259 (19)0.027 (2)−0.0027 (16)−0.0010 (17)−0.0036 (17)
C60.022 (2)0.0194 (18)0.0213 (19)0.0016 (15)−0.0001 (15)−0.0025 (15)
C70.027 (2)0.023 (2)0.023 (2)−0.0003 (16)0.0025 (16)−0.0023 (17)
C80.024 (2)0.0210 (19)0.0204 (19)0.0012 (16)0.0023 (15)0.0044 (16)
C90.020 (2)0.0210 (19)0.026 (2)−0.0012 (15)0.0026 (15)−0.0006 (16)
C100.024 (2)0.0194 (18)0.026 (2)−0.0029 (15)−0.0011 (16)−0.0004 (16)
C110.021 (2)0.026 (2)0.027 (2)0.0027 (16)0.0015 (16)0.0069 (17)
C120.021 (2)0.034 (2)0.024 (2)−0.0065 (16)−0.0014 (16)0.0038 (17)
C130.0173 (19)0.030 (2)0.022 (2)−0.0030 (15)0.0012 (15)0.0012 (16)
C140.022 (2)0.0202 (18)0.026 (2)0.0023 (15)0.0040 (16)0.0021 (16)
C150.030 (2)0.031 (2)0.029 (2)0.0032 (17)−0.0061 (17)0.0083 (18)
C160.049 (3)0.026 (2)0.039 (3)0.0062 (19)−0.010 (2)0.0105 (19)
C170.034 (2)0.038 (2)0.033 (2)−0.0044 (19)−0.0040 (19)0.0092 (19)
C180.033 (3)0.053 (3)0.043 (3)0.014 (2)−0.003 (2)0.014 (2)
C190.017 (2)0.028 (2)0.033 (2)−0.0039 (16)0.0008 (16)−0.0062 (18)
C200.035 (3)0.052 (3)0.044 (3)−0.015 (2)0.010 (2)−0.019 (2)
C210.033 (2)0.025 (2)0.048 (3)0.0001 (18)−0.005 (2)−0.0034 (19)
C220.021 (2)0.032 (2)0.036 (2)−0.0071 (17)0.0010 (17)−0.0039 (19)
C230.022 (2)0.031 (2)0.020 (2)0.0029 (16)0.0006 (16)−0.0010 (16)
C240.023 (2)0.033 (2)0.026 (2)−0.0068 (17)0.0013 (17)0.0020 (17)
C250.022 (2)0.044 (2)0.030 (2)−0.0017 (18)0.0005 (17)0.0029 (19)
C260.023 (2)0.042 (2)0.030 (2)0.0068 (18)0.0046 (17)−0.0001 (19)
C270.026 (2)0.029 (2)0.023 (2)0.0053 (16)0.0026 (16)0.0045 (17)
C280.022 (2)0.030 (2)0.0177 (19)0.0012 (16)−0.0013 (15)0.0031 (16)
C290.021 (2)0.031 (2)0.0180 (19)0.0009 (16)−0.0013 (15)0.0035 (16)
C300.022 (2)0.0259 (19)0.024 (2)−0.0046 (16)0.0017 (16)0.0044 (16)
C310.018 (2)0.0246 (19)0.0192 (19)−0.0032 (15)−0.0018 (15)−0.0006 (16)
C320.021 (2)0.0246 (19)0.0201 (19)0.0030 (15)−0.0031 (15)0.0002 (16)
C330.019 (2)0.031 (2)0.0181 (19)−0.0037 (16)−0.0034 (15)−0.0027 (16)
C340.019 (2)0.034 (2)0.020 (2)−0.0005 (16)0.0015 (15)0.0047 (17)
C350.024 (2)0.027 (2)0.022 (2)0.0036 (16)−0.0019 (16)0.0047 (16)
C360.027 (2)0.0233 (19)0.020 (2)−0.0038 (16)−0.0003 (16)0.0019 (16)
C370.026 (2)0.027 (2)0.028 (2)−0.0081 (16)−0.0010 (16)0.0027 (17)
C380.052 (3)0.023 (2)0.058 (3)−0.0012 (19)0.020 (2)0.006 (2)
C390.048 (3)0.052 (3)0.053 (3)−0.029 (2)−0.015 (2)0.008 (2)
C400.038 (3)0.029 (2)0.036 (2)−0.0051 (18)0.0030 (19)0.0038 (19)
C410.030 (2)0.030 (2)0.039 (2)0.0071 (17)0.0091 (19)0.0029 (19)
C420.039 (3)0.052 (3)0.039 (3)0.018 (2)0.000 (2)0.010 (2)
C430.039 (3)0.052 (3)0.042 (3)0.013 (2)0.008 (2)−0.009 (2)
C440.050 (3)0.027 (2)0.077 (4)0.014 (2)0.026 (3)0.004 (2)
C450.097 (5)0.037 (3)0.066 (4)0.020 (3)−0.012 (3)0.007 (3)
C460.203 (9)0.065 (4)0.103 (6)0.038 (5)0.022 (6)0.030 (4)

Geometric parameters (Å, °)

O1—C11.348 (4)C20—H20B0.9800
O1—H1O0.8400C20—H20C0.9800
O2—C71.245 (4)C21—H21A0.9800
O3—C121.364 (4)C21—H21B0.9800
O3—H3O0.8402C21—H21C0.9800
O4—C231.356 (4)C22—H22A0.9800
O4—H4O0.8400C22—H22B0.9800
O5—C291.233 (4)C22—H22C0.9800
O6—C341.377 (4)C23—C241.374 (5)
O6—H6O0.8400C23—C281.411 (5)
O7—C451.443 (6)C24—C251.376 (5)
O7—H7O0.8400C24—H240.9500
O8—C461.438 (7)C25—C261.371 (6)
O8—H8O0.8400C25—H250.9500
N1—C71.341 (4)C26—C271.393 (5)
N1—N21.385 (4)C26—H260.9500
N1—H1N0.8800C27—C281.395 (5)
N2—C81.278 (4)C27—H270.9500
N3—C291.350 (4)C28—C291.481 (5)
N3—N41.379 (4)C30—C311.456 (5)
N3—H3N0.8800C30—H300.9500
N4—C301.284 (4)C31—C361.380 (5)
C1—C21.383 (5)C31—C321.393 (5)
C1—C61.409 (5)C32—C331.376 (5)
C2—C31.368 (5)C32—H320.9500
C2—H20.9500C33—C341.410 (5)
C3—C41.391 (5)C33—C371.539 (5)
C3—H30.9500C34—C351.390 (5)
C4—C51.371 (5)C35—C361.386 (5)
C4—H40.9500C35—C411.537 (5)
C5—C61.404 (5)C36—H360.9500
C5—H50.9500C37—C381.518 (5)
C6—C71.476 (5)C37—C401.534 (5)
C8—C91.456 (5)C37—C391.544 (5)
C8—H80.9500C38—H38A0.9800
C9—C141.382 (5)C38—H38B0.9800
C9—C101.400 (5)C38—H38C0.9800
C10—C111.376 (5)C39—H39A0.9800
C10—H100.9500C39—H39B0.9800
C11—C121.396 (5)C39—H39C0.9800
C11—C151.547 (5)C40—H40A0.9800
C12—C131.409 (5)C40—H40B0.9800
C13—C141.381 (5)C40—H40C0.9800
C13—C191.544 (5)C41—C441.521 (5)
C14—H140.9500C41—C431.544 (6)
C15—C161.523 (5)C41—C421.544 (6)
C15—C181.536 (5)C42—H42A0.9800
C15—C171.537 (5)C42—H42B0.9800
C16—H16A0.9800C42—H42C0.9800
C16—H16B0.9800C43—H43A0.9800
C16—H16C0.9800C43—H43B0.9800
C17—H17A0.9800C43—H43C0.9800
C17—H17B0.9800C44—H44A0.9800
C17—H17C0.9800C44—H44B0.9800
C18—H18A0.9800C44—H44C0.9800
C18—H18B0.9800C45—H45A0.9800
C18—H18C0.9800C45—H45B0.9800
C19—C211.522 (5)C45—H45C0.9800
C19—C201.538 (5)C46—H46A0.9800
C19—C221.545 (5)C46—H46B0.9800
C20—H20A0.9800C46—H46C0.9800
C1—O1—H1O109.5H22B—C22—H22C109.5
C12—O3—H3O130.8O4—C23—C24120.3 (3)
C23—O4—H4O109.5O4—C23—C28119.7 (3)
C34—O6—H6O126.7C24—C23—C28120.0 (3)
C45—O7—H7O109.5C23—C24—C25120.9 (4)
C46—O8—H8O109.5C23—C24—H24119.6
C7—N1—N2118.5 (3)C25—C24—H24119.6
C7—N1—H1N120.7C26—C25—C24120.3 (4)
N2—N1—H1N120.7C26—C25—H25119.9
C8—N2—N1115.0 (3)C24—C25—H25119.9
C29—N3—N4120.9 (3)C25—C26—C27119.9 (4)
C29—N3—H3N119.6C25—C26—H26120.0
N4—N3—H3N119.6C27—C26—H26120.0
C30—N4—N3113.7 (3)C26—C27—C28120.5 (4)
O1—C1—C2118.4 (3)C26—C27—H27119.7
O1—C1—C6122.0 (3)C28—C27—H27119.7
C2—C1—C6119.7 (3)C27—C28—C23118.4 (3)
C3—C2—C1120.6 (4)C27—C28—C29116.9 (3)
C3—C2—H2119.7C23—C28—C29124.7 (3)
C1—C2—H2119.7O5—C29—N3121.8 (3)
C2—C3—C4120.6 (4)O5—C29—C28121.5 (3)
C2—C3—H3119.7N3—C29—C28116.7 (3)
C4—C3—H3119.7N4—C30—C31123.1 (3)
C5—C4—C3119.7 (4)N4—C30—H30118.4
C5—C4—H4120.2C31—C30—H30118.4
C3—C4—H4120.2C36—C31—C32119.2 (3)
C4—C5—C6120.8 (3)C36—C31—C30118.1 (3)
C4—C5—H5119.6C32—C31—C30122.7 (3)
C6—C5—H5119.6C33—C32—C31121.6 (3)
C5—C6—C1118.6 (3)C33—C32—H32119.2
C5—C6—C7122.9 (3)C31—C32—H32119.2
C1—C6—C7118.5 (3)C32—C33—C34116.8 (3)
O2—C7—N1120.8 (3)C32—C33—C37120.7 (3)
O2—C7—C6121.2 (3)C34—C33—C37122.5 (3)
N1—C7—C6118.0 (3)O6—C34—C35120.7 (3)
N2—C8—C9122.4 (3)O6—C34—C33115.8 (3)
N2—C8—H8118.8C35—C34—C33123.5 (3)
C9—C8—H8118.8C36—C35—C34116.5 (3)
C14—C9—C10118.4 (3)C36—C35—C41120.4 (3)
C14—C9—C8119.2 (3)C34—C35—C41123.1 (3)
C10—C9—C8122.4 (3)C31—C36—C35122.3 (3)
C11—C10—C9121.6 (3)C31—C36—H36118.9
C11—C10—H10119.2C35—C36—H36118.9
C9—C10—H10119.2C38—C37—C40106.8 (3)
C10—C11—C12118.1 (3)C38—C37—C33111.6 (3)
C10—C11—C15120.4 (3)C40—C37—C33111.0 (3)
C12—C11—C15121.5 (3)C38—C37—C39107.9 (4)
O3—C12—C11119.2 (3)C40—C37—C39109.8 (3)
O3—C12—C13118.5 (3)C33—C37—C39109.7 (3)
C11—C12—C13122.3 (3)C37—C38—H38A109.5
C14—C13—C12116.8 (3)C37—C38—H38B109.5
C14—C13—C19120.9 (3)H38A—C38—H38B109.5
C12—C13—C19122.3 (3)C37—C38—H38C109.5
C13—C14—C9122.8 (3)H38A—C38—H38C109.5
C13—C14—H14118.6H38B—C38—H38C109.5
C9—C14—H14118.6C37—C39—H39A109.5
C16—C15—C18107.3 (3)C37—C39—H39B109.5
C16—C15—C17107.2 (3)H39A—C39—H39B109.5
C18—C15—C17110.4 (3)C37—C39—H39C109.5
C16—C15—C11111.5 (3)H39A—C39—H39C109.5
C18—C15—C11110.4 (3)H39B—C39—H39C109.5
C17—C15—C11110.0 (3)C37—C40—H40A109.5
C15—C16—H16A109.5C37—C40—H40B109.5
C15—C16—H16B109.5H40A—C40—H40B109.5
H16A—C16—H16B109.5C37—C40—H40C109.5
C15—C16—H16C109.5H40A—C40—H40C109.5
H16A—C16—H16C109.5H40B—C40—H40C109.5
H16B—C16—H16C109.5C44—C41—C35112.0 (3)
C15—C17—H17A109.5C44—C41—C43107.6 (4)
C15—C17—H17B109.5C35—C41—C43109.8 (3)
H17A—C17—H17B109.5C44—C41—C42105.8 (4)
C15—C17—H17C109.5C35—C41—C42110.5 (3)
H17A—C17—H17C109.5C43—C41—C42111.1 (3)
H17B—C17—H17C109.5C41—C42—H42A109.5
C15—C18—H18A109.5C41—C42—H42B109.5
C15—C18—H18B109.5H42A—C42—H42B109.5
H18A—C18—H18B109.5C41—C42—H42C109.5
C15—C18—H18C109.5H42A—C42—H42C109.5
H18A—C18—H18C109.5H42B—C42—H42C109.5
H18B—C18—H18C109.5C41—C43—H43A109.5
C21—C19—C20107.3 (3)C41—C43—H43B109.5
C21—C19—C13111.3 (3)H43A—C43—H43B109.5
C20—C19—C13110.5 (3)C41—C43—H43C109.5
C21—C19—C22106.8 (3)H43A—C43—H43C109.5
C20—C19—C22110.3 (3)H43B—C43—H43C109.5
C13—C19—C22110.5 (3)C41—C44—H44A109.5
C19—C20—H20A109.5C41—C44—H44B109.5
C19—C20—H20B109.5H44A—C44—H44B109.5
H20A—C20—H20B109.5C41—C44—H44C109.5
C19—C20—H20C109.5H44A—C44—H44C109.5
H20A—C20—H20C109.5H44B—C44—H44C109.5
H20B—C20—H20C109.5O7—C45—H45A109.5
C19—C21—H21A109.5O7—C45—H45B109.5
C19—C21—H21B109.5H45A—C45—H45B109.5
H21A—C21—H21B109.5O7—C45—H45C109.5
C19—C21—H21C109.5H45A—C45—H45C109.5
H21A—C21—H21C109.5H45B—C45—H45C109.5
H21B—C21—H21C109.5O8—C46—H46A109.5
C19—C22—H22A109.5O8—C46—H46B109.5
C19—C22—H22B109.5H46A—C46—H46B109.5
H22A—C22—H22B109.5O8—C46—H46C109.5
C19—C22—H22C109.5H46A—C46—H46C109.5
H22A—C22—H22C109.5H46B—C46—H46C109.5
C7—N1—N2—C8173.1 (3)C12—C13—C19—C22−57.0 (4)
C29—N3—N4—C30168.2 (3)O4—C23—C24—C25−179.0 (4)
O1—C1—C2—C3−178.6 (3)C28—C23—C24—C251.2 (6)
C6—C1—C2—C31.6 (6)C23—C24—C25—C26−1.9 (6)
C1—C2—C3—C40.8 (6)C24—C25—C26—C271.1 (6)
C2—C3—C4—C5−2.0 (6)C25—C26—C27—C280.6 (6)
C3—C4—C5—C60.7 (6)C26—C27—C28—C23−1.3 (5)
C4—C5—C6—C11.7 (5)C26—C27—C28—C29178.4 (3)
C4—C5—C6—C7−180.0 (3)O4—C23—C28—C27−179.4 (3)
O1—C1—C6—C5177.4 (3)C24—C23—C28—C270.4 (5)
C2—C1—C6—C5−2.8 (5)O4—C23—C28—C291.0 (6)
O1—C1—C6—C7−1.1 (5)C24—C23—C28—C29−179.2 (3)
C2—C1—C6—C7178.7 (3)N4—N3—C29—O5−0.3 (5)
N2—N1—C7—O2−1.4 (5)N4—N3—C29—C28179.0 (3)
N2—N1—C7—C6178.9 (3)C27—C28—C29—O5−3.4 (5)
C5—C6—C7—O2−170.8 (3)C23—C28—C29—O5176.2 (3)
C1—C6—C7—O27.5 (5)C27—C28—C29—N3177.3 (3)
C5—C6—C7—N19.0 (5)C23—C28—C29—N3−3.1 (5)
C1—C6—C7—N1−172.7 (3)N3—N4—C30—C31176.9 (3)
N1—N2—C8—C9−179.0 (3)N4—C30—C31—C36177.6 (3)
N2—C8—C9—C14173.4 (3)N4—C30—C31—C32−2.3 (6)
N2—C8—C9—C10−3.7 (5)C36—C31—C32—C330.6 (5)
C14—C9—C10—C11−3.0 (5)C30—C31—C32—C33−179.4 (3)
C8—C9—C10—C11174.1 (3)C31—C32—C33—C34−0.2 (5)
C9—C10—C11—C120.5 (5)C31—C32—C33—C37179.2 (3)
C9—C10—C11—C15−179.6 (3)C32—C33—C34—O6179.0 (3)
C10—C11—C12—O3−176.3 (3)C37—C33—C34—O6−0.4 (5)
C15—C11—C12—O33.8 (5)C32—C33—C34—C35−0.6 (5)
C10—C11—C12—C133.0 (5)C37—C33—C34—C35180.0 (3)
C15—C11—C12—C13−176.9 (3)O6—C34—C35—C36−178.7 (3)
O3—C12—C13—C14175.6 (3)C33—C34—C35—C360.9 (6)
C11—C12—C13—C14−3.7 (5)O6—C34—C35—C41−0.2 (6)
O3—C12—C13—C19−5.6 (5)C33—C34—C35—C41179.4 (3)
C11—C12—C13—C19175.1 (3)C32—C31—C36—C35−0.3 (5)
C12—C13—C14—C91.1 (5)C30—C31—C36—C35179.7 (3)
C19—C13—C14—C9−177.8 (3)C34—C35—C36—C31−0.4 (5)
C10—C9—C14—C132.2 (5)C41—C35—C36—C31−178.9 (3)
C8—C9—C14—C13−175.0 (3)C32—C33—C37—C380.1 (5)
C10—C11—C15—C16−2.1 (5)C34—C33—C37—C38179.4 (3)
C12—C11—C15—C16177.9 (3)C32—C33—C37—C40−119.0 (4)
C10—C11—C15—C18−121.2 (4)C34—C33—C37—C4060.4 (5)
C12—C11—C15—C1858.7 (5)C32—C33—C37—C39119.5 (4)
C10—C11—C15—C17116.7 (4)C34—C33—C37—C39−61.1 (5)
C12—C11—C15—C17−63.4 (4)C36—C35—C41—C44−4.9 (5)
C14—C13—C19—C213.3 (5)C34—C35—C41—C44176.6 (4)
C12—C13—C19—C21−175.5 (3)C36—C35—C41—C43114.5 (4)
C14—C13—C19—C20−115.8 (4)C34—C35—C41—C43−63.9 (5)
C12—C13—C19—C2065.4 (4)C36—C35—C41—C42−122.7 (4)
C14—C13—C19—C22121.8 (4)C34—C35—C41—C4258.9 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1o···O20.841.782.528 (4)147
O4—H4o···O80.841.752.578 (4)167
N1—H1n···O5i0.882.102.763 (4)132
N3—H3n···O40.881.882.592 (4)137
O7—H7o···N20.842.162.900 (4)148
O8—H8o···O70.842.002.704 (5)140

Symmetry codes: (i) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2656).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.
  • Yehye, W. A., Ariffin, A. & Ng, S. W. (2008). Acta Cryst. E64, o961. [PMC free article] [PubMed]

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