10,16-Dichloro-6,20-dioxa-3,23-diaza­tetra­cyclo­[23.3.1.07,12.014,19]nona­cosa-1(29),7,9,11,14(19),15,17,25,27-nona­ene-4,22-dione methanol monosolvate

Pojarová, M.; Dušek, M.; Sedláková, Z.; Makrlík, E.

doi:10.1107/S1600536812007052

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o805-o806

doi:10.1107/S1600536812007052

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10,16-Dichloro-6,20-dioxa-3,23-diazatetracyclo[23.3.1.0^7,12.0^14,19]nonacosa-1(29),7,9,11,14(19),15,17,25,27-nonaene-4,22-dione methanol monosolvate

Michaela Pojarová,^a ^* Michal Dušek,^a Zdeňka Sedláková ^b and Emanuel Makrlík ^c

^aInstitute of Physics of the ASCR, Na Slovance 2, 182 21 Prague 8, Czech Republic, ^bInstitue of Macromolecular Chemistry, ASCR v.v.i., Heyrovského nám. 2, 16202 Prague 6, Czech Republic, and ^cFaculty of Environmental Sciences, Czech University of Life Sciences, Kamýcká 129, 165 21 Prague 6, Czech Republic
^*Correspondence e-mail: pojarova@fzu.cz

(Received 6 February 2012; accepted 16 February 2012; online 24 February 2012)

In the title compound, C₂₅H₂₂Cl₂N₂O₄·CH₃OH, the macrocyclic molecule adopts a slightly distorted C₂-symmetric conformation. The macrocyclic molecules are linked via N—H⋯O hydrogen bonds between the amide groups into chains extending along the [010] direction. The methanol molecules bridge these chains via N—H⋯O and O—H⋯O hydrogen bonds with the formation of a two-dimensional polymeric structure parallel to (001). The methanol molecule is disordered over two positions with the occupancy ratio of 9:1. The disorder of the solvent molecule is caused by weak intermolecular C—H⋯Cl hydrogen bonding.

Related literature

For application of macrocycles, see: Hayvali & Hayvali (2005 ); Kleinpeter et al. (1997 ); Jaiyu et al. (2007 ); Christensen et al. (1997 ); Alexander (1995 ). For the synthetic procedure, see: Ertul et al. (2009 ).

Experimental

Crystal data

C₂₅H₂₂Cl₂N₂O₄·CH₄O
M_r = 517.39
Orthorhombic, P b c a
a = 21.9905 (3) Å
b = 8.1864 (1) Å
c = 26.6760 (3) Å
V = 4802.29 (10) Å³
Z = 8
Cu Kα radiation
μ = 2.78 mm⁻¹
T = 120 K
0.30 × 0.11 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur A Gemini Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.826, T_max = 1.000
42959 measured reflections
4099 independent reflections
3364 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.082
S = 1.03
4099 reflections
326 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O5	0.98	2.31	3.039 (3)	130
N2—H1N2⋯O1ⁱ	0.93	2.20	2.860 (2)	128
O5—H1O5⋯O4ⁱⁱ	0.82	2.05	2.789 (3)	150
C26A—H26F⋯Cl2ⁱⁱⁱ	0.96	2.74	3.616 (3)	149
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) -x+2, -y, -z+1; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ) and ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812007052/gk2457sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812007052/gk2457Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812007052/gk2457Isup3.cml

checkCIF report

Comment top

Polyazalactones together with polyoxalactones and polyethers are studied for their ability to act as multidentate ligands to complex various cations. Polyazalactones can incorporate transition metals into their cavities via an ion-dipole interaction (Hayvali & Hayvali, 2005; Kleinpeter et al., 1997). They are studied for their role in bioprocesses, catalysis, material science, transport and separation (Jaiyu et al., 2007; Christensen et al., 1997; Alexander, 1995). In this paper, we report the crystal structure of a lactam ionophore (Fig.1). The macrocycle consists of three benzene rings, two of them substituted with chlorine atom in para position to O atom. The neighboring molecules are connected via hydrogen bonds between amide groups (Table 1). The crystal contains methanol molecule disordered over two positions with partial occupancies of 0.90 and 0.10. The hydroxyl group of the solvent forms hydrogen bond to the oxygen atom of the amide group (Table 1). The methyl group of the methanol in second position is also weakly bound to the chlorine atoms of neighboring molecule. This weak interaction competes with the stronger hydrogen bond to amide group and causes the solvent disorder.

Related literature top

For application of macrocycles, see: Hayvali & Hayvali (2005); Kleinpeter et al. (1997); Jaiyu et al. (2007); Christensen et al. (1997); Alexander (1995). For the synthetic procedure, see: Ertul et al. (2009).

Experimental top

All chemicals used were purchased from Fluka and used without further purification. The title compound was synthesized according to the method reported by Ertul et al. (2009). Single crystals were prepared by slow evaporation of methanol solution.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. View of the asymmetric unit of the title compound with displacement ellipsoids shown at the 50% probability level. C-bound H atoms have been omitted for clarity.
	Fig. 2. Projection along the b axis with highlighted hydrogen bonds between the molecules. Hydrogen atoms not involved in hydrgen bonding have been omitted.

10,16-Dichloro-6,20-dioxa-3,23- diazatetracyclo[23.3.1.0^7,12.0^14,19]nonacosa- 1(29),7,9,11,14 (19),15,17,25,27-nonaene-4,22-dione methanol monosolvate top

Crystal data top

C₂₅H₂₂Cl₂N₂O₄·CH₄O	D_x = 1.431 Mg m⁻³
M_r = 517.39	Melting point = 316–318 K
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6415 reflections
a = 21.9905 (3) Å	θ = 3.3–67.1°
b = 8.1864 (1) Å	µ = 2.78 mm⁻¹
c = 26.6760 (3) Å	T = 120 K
V = 4802.29 (10) Å³	Prism, colourless
Z = 8	0.30 × 0.11 × 0.08 mm
F(000) = 2160

Data collection top

Oxford Diffraction Xcalibur A Gemini Ultra diffractometer	4099 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	3364 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.070
Detector resolution: 10.3784 pixels mm^-1	θ_max = 65.1°, θ_min = 3.3°
ω scan	h = −22→25
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→9
T_min = 0.826, T_max = 1.000	l = −29→31
42959 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0358P)² + 2.1383P] where P = (F_o² + 2F_c²)/3
4099 reflections	(Δ/σ)_max = 0.002
326 parameters	Δρ_max = 0.20 e Å⁻³
4 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₅H₂₂Cl₂N₂O₄·CH₄O	V = 4802.29 (10) Å³
M_r = 517.39	Z = 8
Orthorhombic, Pbca	Cu Kα radiation
a = 21.9905 (3) Å	µ = 2.78 mm⁻¹
b = 8.1864 (1) Å	T = 120 K
c = 26.6760 (3) Å	0.30 × 0.11 × 0.08 mm

Data collection top

Oxford Diffraction Xcalibur A Gemini Ultra diffractometer	4099 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3364 reflections with I > 2σ(I)
T_min = 0.826, T_max = 1.000	R_int = 0.070
42959 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	4 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.03	Δρ_max = 0.20 e Å⁻³
4099 reflections	Δρ_min = −0.21 e Å⁻³
326 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 > 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. Positions of disordered groups were found from electron density maps. The disordered fragments were then placed in appropriate positions, and all distances between neighbouring atoms were fixed. Site occupancies were refined for the different parts with the same thermal parameters for same atoms in various fragments. At the end of the refinement, site occupancies were fixed at values 0.90 and 0.10 and hydrogen atoms were placed into calculated positions. All hydrogen atoms could be found from maps of difference electron density, but those, attached to carbon atoms, were placed into calculated positions. The distance between N and H atoms were restrained to 1.00 Å with σ=0.02. The isotropic temperature parameters of hydrogen atoms were calculated as 1.2*U_eq of the parent atom.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	1.11069 (2)	0.02416 (7)	0.213524 (18)	0.03911 (14)
Cl2	0.84287 (2)	−0.21013 (7)	0.147714 (18)	0.03856 (14)
O1	0.70542 (6)	0.38705 (18)	0.40933 (5)	0.0367 (3)
O2	0.80594 (5)	0.19883 (17)	0.32491 (5)	0.0305 (3)
O3	0.96571 (6)	−0.16498 (18)	0.38954 (5)	0.0322 (3)
O4	0.98144 (6)	−0.1787 (2)	0.52219 (5)	0.0406 (4)
N1	0.80833 (7)	0.38887 (19)	0.40351 (6)	0.0277 (3)
H1N2	0.8870	−0.1436	0.4391	0.033*
N2	0.89913 (7)	−0.14110 (19)	0.47251 (5)	0.0262 (3)
H1N1	0.8439	0.3425	0.3862	0.031*
C1	0.81828 (9)	0.4614 (2)	0.45255 (7)	0.0315 (4)
H1A	0.7853	0.5366	0.4597	0.038*
H1B	0.8557	0.5239	0.4517	0.038*
C2	0.75257 (8)	0.3497 (2)	0.38745 (7)	0.0266 (4)
C3	0.74788 (8)	0.2590 (2)	0.33841 (7)	0.0265 (4)
H3A	0.7195	0.1690	0.3417	0.032*
H3B	0.7329	0.3318	0.3125	0.032*
C4	0.81162 (8)	0.1097 (2)	0.28177 (6)	0.0240 (4)
C5	0.76696 (8)	0.0977 (2)	0.24538 (7)	0.0267 (4)
H5	0.7306	0.1547	0.2489	0.032*
C6	0.77682 (8)	0.0000 (2)	0.20357 (7)	0.0289 (4)
H6	0.7472	−0.0093	0.1788	0.035*
C7	0.83113 (8)	−0.0828 (2)	0.19935 (7)	0.0276 (4)
C8	0.87611 (8)	−0.0703 (2)	0.23554 (7)	0.0255 (4)
H8	0.9124	−0.1273	0.2317	0.031*
C9	0.86718 (8)	0.0266 (2)	0.27735 (7)	0.0242 (4)
C10	0.91217 (8)	0.0476 (3)	0.31990 (7)	0.0338 (5)
H10A	0.9167	0.1636	0.3263	0.041*
H10B	0.8947	−0.0011	0.3498	0.041*
C11	0.97467 (8)	−0.0239 (2)	0.31231 (7)	0.0283 (4)
C12	1.00962 (8)	0.0216 (2)	0.27119 (7)	0.0296 (4)
H12	0.9936	0.0927	0.2474	0.035*
C13	1.06813 (8)	−0.0383 (2)	0.26540 (7)	0.0298 (4)
C14	1.09288 (8)	−0.1440 (3)	0.29985 (7)	0.0317 (4)
H14	1.1320	−0.1849	0.2953	0.038*
C15	1.05893 (9)	−0.1890 (3)	0.34134 (7)	0.0313 (4)
H15	1.0753	−0.2604	0.3649	0.038*
C16	1.00041 (8)	−0.1277 (2)	0.34793 (7)	0.0275 (4)
C17	0.99810 (9)	−0.1964 (3)	0.43499 (7)	0.0345 (5)
H17A	1.0330	−0.1243	0.4370	0.041*
H17B	1.0128	−0.3081	0.4348	0.041*
C18	0.95804 (9)	−0.1705 (2)	0.48030 (7)	0.0291 (4)
C19	0.85686 (9)	−0.1157 (2)	0.51386 (7)	0.0287 (4)
H19A	0.8741	−0.1632	0.5440	0.034*
H19B	0.8194	−0.1736	0.5066	0.034*
C20	0.84194 (8)	0.0621 (2)	0.52404 (7)	0.0261 (4)
C21	0.82821 (8)	0.1118 (3)	0.57256 (7)	0.0307 (4)
H21	0.8297	0.0368	0.5987	0.037*
C22	0.81235 (9)	0.2726 (3)	0.58206 (7)	0.0350 (5)
H22	0.8037	0.3052	0.6147	0.042*
C23	0.80922 (8)	0.3850 (3)	0.54350 (8)	0.0321 (4)
H23	0.7985	0.4927	0.5503	0.039*
C24	0.82213 (8)	0.3373 (2)	0.49450 (7)	0.0271 (4)
C25	0.83856 (8)	0.1760 (2)	0.48543 (7)	0.0264 (4)
H25	0.8475	0.1435	0.4528	0.032*
O5	0.94522 (11)	0.3414 (4)	0.40875 (11)	0.0418 (7)	0.90
H1O5	0.9545	0.2931	0.4346	0.050*	0.90
C26	0.99892 (15)	0.3791 (5)	0.38117 (9)	0.0415 (7)	0.90
H26A	0.9904	0.4652	0.3578	0.050*	0.90
H26B	1.0123	0.2838	0.3633	0.050*	0.90
H26C	1.0303	0.4138	0.4039	0.050*	0.90
O5A	0.9587 (14)	0.374 (5)	0.4090 (12)	0.0418 (7)	0.10
H2O5	0.9634	0.2905	0.4254	0.050*	0.10
C26A	0.9961 (18)	0.367 (6)	0.3651 (11)	0.0415 (7)	0.10
H26D	0.9888	0.4625	0.3449	0.050*	0.10
H26E	0.9863	0.2711	0.3462	0.050*	0.10
H26F	1.0381	0.3642	0.3748	0.050*	0.10

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0270 (2)	0.0524 (3)	0.0380 (3)	−0.0081 (2)	0.00832 (19)	−0.0091 (2)
Cl2	0.0337 (3)	0.0480 (3)	0.0339 (3)	−0.0041 (2)	0.00026 (19)	−0.0116 (2)
O1	0.0250 (7)	0.0434 (9)	0.0417 (8)	0.0047 (6)	0.0079 (6)	−0.0067 (7)
O2	0.0183 (6)	0.0437 (8)	0.0294 (7)	0.0064 (6)	0.0010 (5)	−0.0059 (6)
O3	0.0221 (6)	0.0499 (9)	0.0245 (6)	0.0021 (6)	−0.0020 (5)	−0.0013 (6)
O4	0.0343 (8)	0.0595 (10)	0.0279 (7)	0.0096 (7)	−0.0066 (6)	0.0019 (7)
N1	0.0236 (8)	0.0284 (8)	0.0311 (8)	0.0029 (7)	0.0014 (6)	0.0015 (7)
N2	0.0254 (8)	0.0302 (9)	0.0230 (7)	0.0009 (7)	−0.0009 (6)	−0.0013 (6)
C1	0.0290 (10)	0.0283 (10)	0.0372 (11)	0.0017 (8)	−0.0014 (8)	−0.0044 (8)
C2	0.0242 (9)	0.0240 (10)	0.0315 (9)	0.0042 (8)	0.0035 (8)	0.0059 (8)
C3	0.0185 (8)	0.0298 (10)	0.0313 (9)	0.0057 (8)	0.0024 (7)	0.0050 (8)
C4	0.0216 (9)	0.0264 (9)	0.0241 (9)	−0.0010 (8)	0.0028 (7)	0.0051 (7)
C5	0.0184 (9)	0.0314 (10)	0.0302 (10)	0.0002 (8)	0.0002 (7)	0.0092 (8)
C6	0.0232 (9)	0.0359 (11)	0.0276 (10)	−0.0049 (8)	−0.0033 (7)	0.0064 (8)
C7	0.0261 (9)	0.0306 (10)	0.0260 (9)	−0.0053 (8)	0.0020 (7)	0.0013 (8)
C8	0.0208 (9)	0.0279 (10)	0.0277 (9)	−0.0002 (8)	0.0029 (7)	0.0043 (8)
C9	0.0194 (8)	0.0284 (10)	0.0247 (9)	−0.0012 (8)	0.0021 (7)	0.0058 (7)
C10	0.0218 (9)	0.0515 (13)	0.0280 (10)	0.0097 (9)	−0.0010 (8)	−0.0040 (9)
C11	0.0196 (9)	0.0398 (11)	0.0256 (9)	0.0026 (8)	−0.0024 (7)	−0.0082 (8)
C12	0.0233 (9)	0.0364 (11)	0.0290 (9)	0.0024 (8)	−0.0018 (8)	−0.0056 (8)
C13	0.0212 (9)	0.0383 (11)	0.0300 (10)	−0.0042 (8)	0.0019 (7)	−0.0109 (8)
C14	0.0186 (9)	0.0406 (12)	0.0359 (10)	0.0022 (8)	−0.0019 (8)	−0.0131 (9)
C15	0.0248 (10)	0.0374 (11)	0.0317 (10)	0.0055 (8)	−0.0048 (8)	−0.0076 (8)
C16	0.0207 (9)	0.0356 (11)	0.0262 (9)	−0.0002 (8)	−0.0017 (7)	−0.0074 (8)
C17	0.0294 (10)	0.0463 (13)	0.0278 (10)	0.0091 (9)	−0.0037 (8)	−0.0014 (9)
C18	0.0291 (10)	0.0313 (11)	0.0271 (10)	0.0028 (8)	−0.0027 (8)	0.0004 (8)
C19	0.0264 (9)	0.0326 (11)	0.0270 (9)	−0.0017 (8)	0.0027 (7)	0.0020 (8)
C20	0.0177 (8)	0.0335 (10)	0.0271 (9)	−0.0020 (8)	−0.0015 (7)	−0.0035 (8)
C21	0.0236 (9)	0.0434 (12)	0.0251 (9)	−0.0008 (9)	−0.0002 (7)	0.0004 (8)
C22	0.0286 (10)	0.0494 (13)	0.0271 (10)	0.0025 (9)	0.0009 (8)	−0.0109 (9)
C23	0.0235 (9)	0.0346 (11)	0.0383 (11)	0.0034 (9)	−0.0017 (8)	−0.0098 (9)
C24	0.0176 (9)	0.0334 (11)	0.0301 (10)	−0.0008 (8)	−0.0022 (7)	−0.0048 (8)
C25	0.0215 (9)	0.0334 (11)	0.0245 (9)	−0.0007 (8)	0.0011 (7)	−0.0047 (8)
O5	0.0243 (15)	0.0620 (19)	0.0390 (8)	0.0036 (10)	−0.0010 (10)	0.0116 (10)
C26	0.0367 (13)	0.0549 (17)	0.0330 (17)	−0.0057 (12)	−0.0024 (16)	0.0023 (19)
O5A	0.0243 (15)	0.0620 (19)	0.0390 (8)	0.0036 (10)	−0.0010 (10)	0.0116 (10)
C26A	0.0367 (13)	0.0549 (17)	0.0330 (17)	−0.0057 (12)	−0.0024 (16)	0.0023 (19)

Geometric parameters (Å, º) top

Cl1—C13	1.7470 (19)	C11—C16	1.395 (3)
Cl2—C7	1.7466 (19)	C12—C13	1.386 (3)
O1—C2	1.229 (2)	C12—H12	0.9300
O2—C4	1.368 (2)	C13—C14	1.375 (3)
O2—C3	1.415 (2)	C14—C15	1.385 (3)
O3—C16	1.381 (2)	C14—H14	0.9300
O3—C17	1.430 (2)	C15—C16	1.392 (3)
O4—C18	1.232 (2)	C15—H15	0.9300
N1—C2	1.338 (2)	C17—C18	1.511 (3)
N1—C1	1.453 (2)	C17—H17A	0.9700
N1—H1N1	0.9840	C17—H17B	0.9700
N2—C18	1.334 (2)	C19—C20	1.517 (3)
N2—C19	1.458 (2)	C19—H19A	0.9700
N2—H1N2	0.9295	C19—H19B	0.9700
C1—C24	1.514 (3)	C20—C21	1.390 (3)
C1—H1A	0.9700	C20—C25	1.391 (3)
C1—H1B	0.9700	C21—C22	1.385 (3)
C2—C3	1.507 (3)	C21—H21	0.9300
C3—H3A	0.9700	C22—C23	1.382 (3)
C3—H3B	0.9700	C22—H22	0.9300
C4—C5	1.384 (3)	C23—C24	1.394 (3)
C4—C9	1.404 (3)	C23—H23	0.9300
C5—C6	1.389 (3)	C24—C25	1.391 (3)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.378 (3)	O5—C26	1.425 (3)
C6—H6	0.9300	O5—H1O5	0.8200
C7—C8	1.386 (3)	C26—H26A	0.9600
C8—C9	1.383 (3)	C26—H26B	0.9600
C8—H8	0.9300	C26—H26C	0.9600
C9—C10	1.516 (3)	O5A—C26A	1.430 (19)
C10—C11	1.508 (3)	O5A—H2O5	0.8200
C10—H10A	0.9700	C26A—H26D	0.9600
C10—H10B	0.9700	C26A—H26E	0.9600
C11—C12	1.390 (3)	C26A—H26F	0.9600

C4—O2—C3	118.82 (14)	C14—C13—C12	121.06 (18)
C16—O3—C17	116.49 (14)	C14—C13—Cl1	120.10 (14)
C2—N1—C1	121.63 (16)	C12—C13—Cl1	118.83 (16)
C2—N1—H1N1	119.0	C13—C14—C15	119.22 (17)
C1—N1—H1N1	117.4	C13—C14—H14	120.4
C18—N2—C19	121.82 (15)	C15—C14—H14	120.4
C18—N2—H1N2	115.1	C14—C15—C16	120.21 (19)
C19—N2—H1N2	123.0	C14—C15—H15	119.9
N1—C1—C24	113.56 (16)	C16—C15—H15	119.9
N1—C1—H1A	108.9	O3—C16—C15	122.18 (17)
C24—C1—H1A	108.9	O3—C16—C11	117.25 (16)
N1—C1—H1B	108.9	C15—C16—C11	120.58 (18)
C24—C1—H1B	108.9	O3—C17—C18	111.27 (15)
H1A—C1—H1B	107.7	O3—C17—H17A	109.4
O1—C2—N1	124.17 (18)	C18—C17—H17A	109.4
O1—C2—C3	118.49 (17)	O3—C17—H17B	109.4
N1—C2—C3	117.30 (16)	C18—C17—H17B	109.4
O2—C3—C2	109.29 (15)	H17A—C17—H17B	108.0
O2—C3—H3A	109.8	O4—C18—N2	123.83 (18)
C2—C3—H3A	109.8	O4—C18—C17	118.33 (17)
O2—C3—H3B	109.8	N2—C18—C17	117.84 (16)
C2—C3—H3B	109.8	N2—C19—C20	114.22 (15)
H3A—C3—H3B	108.3	N2—C19—H19A	108.7
O2—C4—C5	124.25 (16)	C20—C19—H19A	108.7
O2—C4—C9	114.12 (15)	N2—C19—H19B	108.7
C5—C4—C9	121.62 (17)	C20—C19—H19B	108.7
C4—C5—C6	119.53 (17)	H19A—C19—H19B	107.6
C4—C5—H5	120.2	C21—C20—C25	118.80 (18)
C6—C5—H5	120.2	C21—C20—C19	119.64 (17)
C7—C6—C5	118.96 (17)	C25—C20—C19	121.47 (16)
C7—C6—H6	120.5	C22—C21—C20	120.21 (19)
C5—C6—H6	120.5	C22—C21—H21	119.9
C6—C7—C8	121.69 (18)	C20—C21—H21	119.9
C6—C7—Cl2	119.10 (14)	C23—C22—C21	120.62 (18)
C8—C7—Cl2	119.19 (15)	C23—C22—H22	119.7
C9—C8—C7	120.19 (17)	C21—C22—H22	119.7
C9—C8—H8	119.9	C22—C23—C24	120.08 (19)
C7—C8—H8	119.9	C22—C23—H23	120.0
C8—C9—C4	118.01 (16)	C24—C23—H23	120.0
C8—C9—C10	125.23 (16)	C25—C24—C23	118.84 (18)
C4—C9—C10	116.75 (16)	C25—C24—C1	121.56 (17)
C11—C10—C9	116.76 (16)	C23—C24—C1	119.60 (18)
C11—C10—H10A	108.1	C24—C25—C20	121.43 (17)
C9—C10—H10A	108.1	C24—C25—H25	119.3
C11—C10—H10B	108.1	C20—C25—H25	119.3
C9—C10—H10B	108.1	C26—O5—H1O5	109.5
H10A—C10—H10B	107.3	C26A—O5A—H2O5	109.5
C12—C11—C16	118.45 (17)	O5A—C26A—H26D	109.5
C12—C11—C10	120.39 (18)	O5A—C26A—H26E	109.5
C16—C11—C10	121.00 (17)	H26D—C26A—H26E	109.5
C13—C12—C11	120.43 (19)	O5A—C26A—H26F	109.5
C13—C12—H12	119.8	H26D—C26A—H26F	109.5
C11—C12—H12	119.8	H26E—C26A—H26F	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O5	0.98	2.31	3.039 (3)	130
N2—H1N2···O1ⁱ	0.93	2.20	2.860 (2)	128
O5—H1O5···O4ⁱⁱ	0.82	2.05	2.789 (3)	150
C26A—H26F···Cl2ⁱⁱⁱ	0.96	2.74	3.616 (3)	149

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) −x+2, −y, −z+1; (iii) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₂Cl₂N₂O₄·CH₄O
M_r	517.39
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	120
a, b, c (Å)	21.9905 (3), 8.1864 (1), 26.6760 (3)
V (Å³)	4802.29 (10)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	2.78
Crystal size (mm)	0.30 × 0.11 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur A Gemini Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.826, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	42959, 4099, 3364
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.588

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.082, 1.03
No. of reflections	4099
No. of parameters	326
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006) and ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O5	0.98	2.31	3.039 (3)	130
N2—H1N2···O1ⁱ	0.93	2.20	2.860 (2)	128
O5—H1O5···O4ⁱⁱ	0.82	2.05	2.789 (3)	150
C26A—H26F···Cl2ⁱⁱⁱ	0.96	2.74	3.616 (3)	149

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) −x+2, −y, −z+1; (iii) −x+2, y+1/2, −z+1/2.

Acknowledgements

This study was financially supported by the Institutional Research Plan No. AVOZ10100521 of the Institute of Physics, the project Praemium Academiae of the Academy of Science of the Czech Republic, the Grant Agency of the Faculty of Environmental Sciences, Czech University of Life Sciences, Prague (project No. 42900/1312/3114 `Environmental Aspects of Sustainable Development of Society'), and the Czech Ministry of Education, Youth and Sports (Project MSM 6046137307).

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Alexander, V. (1995). Chem. Rev. 95, 273–342. CrossRef CAS Web of Science Google Scholar
Christensen, A., Jensen, H. S., McKee, V., Mckenzie, C. J. & Munch, M. (1997). Inorg. Chem. 36, 6080–6085. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ertul, S., Tombak, A. H., Bayrakci, M. & Merter, O. (2009). Acta Chim. Slov. 56, 878–884. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hayvali, M. & Hayvali, Z. (2005). Synth. React. Inorg. Met. Org. Chem. 34, 713–732. Google Scholar
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Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 68| Part 3| March 2012| Pages o805-o806

doi:10.1107/S1600536812007052

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

10,16-Di­chloro-6,20-dioxa-3,23-di­aza­tetra­cyclo­[23.3.1.07,12.014,19]nona­cosa-1(29),7,9,11,14(19),15,17,25,27-nona­ene-4,22-dione methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

10,16-Dichloro-6,20-dioxa-3,23-diazatetracyclo[23.3.1.0^7,12.0^14,19]nonacosa-1(29),7,9,11,14(19),15,17,25,27-nonaene-4,22-dione methanol monosolvate