2,17-Dichloro-8,9,10,11-tetra­hydro-19H-dibenzo[k,n][1,10,4,7]dioxadiaza­cyclo­penta­decine-7,12(6H,13H)-dione

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

doi:10.1107/S1600536812020351

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Pages o1698-o1699

doi:10.1107/S1600536812020351

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2,17-Dichloro-8,9,10,11-tetrahydro-19H-dibenzo[k,n][1,10,4,7]dioxadiazacyclopentadecine-7,12(6H,13H)-dione

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

^aInstitute of Physics, AS CR, v.v.i., Na Slovance 2, 182 21 Prague 8, Czech Republic, ^bInstitute of Macromolecular Chemistry, AS CR v.v.i., Heyrovského nám. 2, 162 06 Prague 6, Czech Republic, and ^cFaculty of Environmental Sciences, Czech University of Life Sciences, Prague, Kamýcká 129, 165 21 Prague 6, Czech Republic
^*Correspondence e-mail: pojarova@fzu.cz

(Received 12 April 2012; accepted 6 May 2012; online 12 May 2012)

In the crystal structure of the title compound, C₁₉H₁₈Cl₂N₂O₄, N—H⋯O hydrogen bonds link the molecules into infinite chains along the b axis. The structure also features weak C—H⋯O and C—H⋯Cl hydrogen bonds and C—H⋯π and (lone pair)⋯π interactions [Cl⋯centroid = 3.5871 (7) Å]. An intramolecular N—H⋯O bond occurs.

Related literature

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

Experimental

Crystal data

C₁₉H₁₈Cl₂N₂O₄
M_r = 409.25
Monoclinic, P 2₁ /c
a = 12.0877 (3) Å
b = 8.73462 (15) Å
c = 17.3712 (4) Å
β = 93.588 (2)°
V = 1830.48 (7) Å³
Z = 4
Cu Kα radiation
μ = 3.44 mm⁻¹
T = 120 K
0.31 × 0.22 × 0.21 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010 ) T_min = 0.175, T_max = 0.342
19596 measured reflections
3271 independent reflections
3210 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.074
S = 1.07
3271 reflections
244 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2ⁱ	0.89	2.05	2.8945 (15)	158
C14—H14A⋯O3ⁱ	0.97	2.54	3.5026 (17)	172
C14—H14B⋯O3ⁱⁱ	0.97	2.34	3.2934 (17)	167
C16—H16B⋯O1ⁱⁱⁱ	0.97	2.59	3.2843 (17)	129
C19—H19A⋯Cl2^iv	0.97	2.81	3.6201 (14)	142
C9—H9⋯Cg1^v	0.93	2.88	3.8006 (14)	174
N1—H1N1⋯O1	0.90	2.16	2.5935 (15)	109
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812020351/aa2058sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812020351/aa2058Isup2.hkl

checkCIF report

Comment top

Polyazalactones together with polyoxalactones and polyethers are studied for their ability to act as multidentate ligands and to complex various cations. Polyazalactones can incorporate transition metals into their cavities via an ion-dipole interaction (Hayvali et al., 2005; Kleinpeter et al., 1997). They are studied for their role in bioprocesses, catalysis, material science, and transport and separation (Jaiyu et al., 2007; Christensen et al., 1997; Alexander, 1995). In this paper, we report a crystal structure of lactam ionophore (Fig. 1 and Scheme). The macrocycle consists of two phenyl rings substituted with chlorine atom in para position. The neighbouring molecules are connected via hydrogen bonds between amide groups (Fig. 1 and Table 1). Weaker hydrogen bonds can be found between methylene groups and oxygen or chlorine atoms. The arrangement of the molecules in the crystal is influenced by the C—H···π interactions between the aromatic rings (C9—H9··· C1→C6 (Cg1)) and lone pair···π interaction between the chlorine atom Cl1 and neighbouring aromatic ring C8→C13(Cg2) (the distance between Cl1 and Cg2 is 3.5871 (7) Å).

Related literature top

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

Experimental top

All chemicals used were purchased from Fluka and used without further purification. The title compound was synthesized by means of method published by Ertul et al. (2009). Crystals were prepared by slow evaporation from methanol.

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 title compound, together with atom-labelling scheme. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. Projection along the b axis with highlighted hydrogen bonds between the molecules.

2,17-Dichloro-8,9,10,11-tetrahydro-19H- dibenzo[k,n][1,10,4,7]dioxadiazacyclopentadecine- 7,12(6H,13H)-dione top

Crystal data top

C₁₉H₁₈Cl₂N₂O₄	F(000) = 848
M_r = 409.25	D_x = 1.484 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 16650 reflections
a = 12.0877 (3) Å	θ = 3.7–67.1°
b = 8.73462 (15) Å	µ = 3.44 mm⁻¹
c = 17.3712 (4) Å	T = 120 K
β = 93.588 (2)°	Prism, colourless
V = 1830.48 (7) Å³	0.31 × 0.22 × 0.21 mm
Z = 4

Data collection top

Agilent Xcalibur Atlas Gemini ultra diffractometer	3271 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	3210 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 10.3784 pixels mm^-1	θ_max = 67.1°, θ_min = 3.7°
Rotation method data acquisition using ω scans	h = −14→14
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	k = −8→10
T_min = 0.175, T_max = 0.342	l = −20→20
19596 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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.074	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0376P)² + 0.7612P] where P = (F_o² + 2F_c²)/3
3271 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.20 e Å⁻³
2 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₉H₁₈Cl₂N₂O₄	V = 1830.48 (7) Å³
M_r = 409.25	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.0877 (3) Å	µ = 3.44 mm⁻¹
b = 8.73462 (15) Å	T = 120 K
c = 17.3712 (4) Å	0.31 × 0.22 × 0.21 mm
β = 93.588 (2)°

Data collection top

Agilent Xcalibur Atlas Gemini ultra diffractometer	3271 independent reflections
Absorption correction: analytical (CrysAlis PRO; Agilent, 2010)	3210 reflections with I > 2σ(I)
T_min = 0.175, T_max = 0.342	R_int = 0.028
19596 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	2 restraints
wR(F²) = 0.074	H-atom parameters constrained
S = 1.07	Δρ_max = 0.20 e Å⁻³
3271 reflections	Δρ_min = −0.29 e Å⁻³
244 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The distance between hydrogen atoms and nitrogen atoms was restrained. The bond length was set to 0.87 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
Cl1	0.86335 (3)	1.01411 (4)	0.16078 (2)	0.03147 (11)
Cl2	1.00225 (3)	0.24819 (5)	−0.01843 (2)	0.03989 (12)
O4	0.78538 (8)	0.52610 (11)	0.38371 (5)	0.0251 (2)
O1	0.64125 (7)	0.49162 (11)	0.15585 (5)	0.0248 (2)
O3	0.58083 (8)	0.72265 (11)	0.47012 (6)	0.0306 (2)
O2	0.39104 (8)	0.69986 (11)	0.15386 (6)	0.0291 (2)
N2	0.55581 (9)	0.49941 (13)	0.40482 (6)	0.0247 (2)
H1N2	0.5904	0.4132	0.3923	0.030*
C19	0.74034 (11)	0.56132 (16)	0.45584 (8)	0.0262 (3)
H19A	0.7809	0.6463	0.4799	0.031*
H19B	0.7490	0.4736	0.4899	0.031*
C3	0.79942 (11)	0.91308 (16)	0.29832 (8)	0.0269 (3)
H3	0.7880	1.0154	0.3102	0.032*
C5	0.84978 (11)	0.71987 (16)	0.20783 (8)	0.0241 (3)
H5	0.8732	0.6951	0.1594	0.029*
C11	0.79350 (12)	0.34870 (16)	−0.00686 (8)	0.0276 (3)
H11	0.7834	0.3274	−0.0593	0.033*
C8	0.82559 (11)	0.40890 (14)	0.15178 (8)	0.0222 (3)
C1	0.79727 (10)	0.64599 (15)	0.33323 (8)	0.0230 (3)
C6	0.82934 (10)	0.60427 (15)	0.25987 (8)	0.0223 (3)
C7	0.83966 (11)	0.43695 (15)	0.23779 (8)	0.0237 (3)
H7A	0.9119	0.3998	0.2567	0.028*
H7B	0.7842	0.3784	0.2631	0.028*
C13	0.72294 (11)	0.43609 (15)	0.11165 (8)	0.0228 (3)
C9	0.91159 (11)	0.35413 (15)	0.11042 (8)	0.0248 (3)
H9	0.9809	0.3374	0.1352	0.030*
C12	0.70686 (11)	0.40584 (16)	0.03341 (8)	0.0268 (3)
H12	0.6381	0.4238	0.0079	0.032*
N1	0.49166 (10)	0.57462 (14)	0.24811 (7)	0.0271 (3)
H1N1	0.5560	0.5268	0.2600	0.033*
C15	0.46922 (10)	0.61525 (15)	0.17506 (8)	0.0230 (3)
C14	0.54225 (11)	0.54793 (16)	0.11649 (8)	0.0242 (3)
H14A	0.5038	0.4652	0.0889	0.029*
H14B	0.5604	0.6256	0.0794	0.029*
C18	0.61793 (11)	0.60295 (15)	0.44482 (7)	0.0242 (3)
C2	0.78030 (11)	0.79873 (16)	0.35175 (8)	0.0263 (3)
H2	0.7562	0.8245	0.3999	0.032*
C4	0.83550 (11)	0.87211 (16)	0.22751 (8)	0.0250 (3)
C17	0.44063 (11)	0.52947 (16)	0.38020 (8)	0.0270 (3)
H17A	0.4034	0.5749	0.4225	0.032*
H17B	0.4038	0.4337	0.3666	0.032*
C10	0.89470 (11)	0.32410 (16)	0.03211 (8)	0.0268 (3)
C16	0.43191 (11)	0.63655 (16)	0.31133 (8)	0.0276 (3)
H16A	0.3546	0.6506	0.2945	0.033*
H16B	0.4624	0.7357	0.3262	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0375 (2)	0.02398 (18)	0.0333 (2)	−0.00168 (13)	0.00512 (14)	0.00670 (13)
Cl2	0.0333 (2)	0.0531 (2)	0.0343 (2)	0.01109 (16)	0.00956 (15)	−0.00592 (16)
O4	0.0283 (5)	0.0241 (5)	0.0232 (5)	0.0001 (4)	0.0043 (4)	0.0026 (4)
O1	0.0209 (5)	0.0307 (5)	0.0227 (5)	0.0044 (4)	0.0010 (4)	0.0008 (4)
O3	0.0355 (5)	0.0277 (5)	0.0291 (5)	0.0002 (4)	0.0056 (4)	−0.0042 (4)
O2	0.0259 (5)	0.0293 (5)	0.0323 (5)	0.0061 (4)	0.0027 (4)	0.0076 (4)
N2	0.0253 (6)	0.0234 (6)	0.0255 (6)	0.0011 (4)	0.0013 (5)	0.0001 (4)
C19	0.0294 (7)	0.0287 (7)	0.0205 (6)	−0.0023 (6)	0.0020 (5)	0.0012 (5)
C3	0.0283 (7)	0.0210 (7)	0.0313 (7)	0.0004 (5)	0.0005 (5)	−0.0014 (5)
C5	0.0233 (6)	0.0260 (7)	0.0232 (6)	−0.0011 (5)	0.0025 (5)	0.0002 (5)
C11	0.0333 (7)	0.0268 (7)	0.0227 (7)	0.0004 (6)	0.0034 (5)	0.0003 (5)
C8	0.0246 (6)	0.0161 (6)	0.0258 (7)	−0.0012 (5)	0.0014 (5)	0.0019 (5)
C1	0.0198 (6)	0.0244 (7)	0.0245 (6)	−0.0019 (5)	−0.0006 (5)	0.0030 (5)
C6	0.0181 (6)	0.0226 (6)	0.0259 (7)	−0.0004 (5)	−0.0008 (5)	0.0004 (5)
C7	0.0239 (6)	0.0224 (6)	0.0248 (7)	0.0012 (5)	0.0004 (5)	0.0013 (5)
C13	0.0235 (6)	0.0201 (6)	0.0251 (7)	0.0004 (5)	0.0041 (5)	0.0011 (5)
C9	0.0231 (6)	0.0213 (6)	0.0299 (7)	−0.0002 (5)	0.0015 (5)	0.0019 (5)
C12	0.0257 (7)	0.0284 (7)	0.0261 (7)	0.0022 (5)	−0.0001 (5)	0.0016 (5)
N1	0.0258 (6)	0.0309 (6)	0.0247 (6)	0.0087 (5)	0.0016 (4)	0.0007 (5)
C15	0.0211 (6)	0.0195 (6)	0.0283 (7)	−0.0029 (5)	0.0007 (5)	0.0018 (5)
C14	0.0222 (6)	0.0256 (7)	0.0244 (7)	0.0016 (5)	−0.0008 (5)	0.0036 (5)
C18	0.0301 (7)	0.0246 (7)	0.0183 (6)	−0.0015 (5)	0.0042 (5)	0.0030 (5)
C2	0.0267 (7)	0.0278 (7)	0.0248 (7)	0.0005 (5)	0.0034 (5)	−0.0028 (6)
C4	0.0240 (6)	0.0231 (7)	0.0278 (7)	−0.0014 (5)	0.0001 (5)	0.0045 (5)
C17	0.0244 (7)	0.0300 (7)	0.0268 (7)	−0.0005 (5)	0.0031 (5)	0.0003 (6)
C10	0.0279 (7)	0.0237 (7)	0.0295 (7)	0.0020 (5)	0.0082 (5)	0.0001 (5)
C16	0.0277 (7)	0.0292 (7)	0.0262 (7)	0.0057 (6)	0.0030 (5)	−0.0006 (6)

Geometric parameters (Å, º) top

Cl1—C4	1.7451 (14)	C8—C13	1.4050 (18)
Cl2—C10	1.7448 (14)	C8—C7	1.5132 (18)
O4—C1	1.3794 (16)	C1—C2	1.391 (2)
O4—C19	1.4306 (16)	C1—C6	1.4031 (19)
O1—C13	1.3766 (16)	C6—C7	1.5185 (19)
O1—C14	1.4282 (15)	C7—H7A	0.9700
O3—C18	1.2300 (17)	C7—H7B	0.9700
O2—C15	1.2377 (16)	C13—C12	1.3864 (19)
N2—C18	1.3417 (18)	C9—C10	1.388 (2)
N2—C17	1.4548 (17)	C9—H9	0.9300
N2—H1N2	0.8948	C12—H12	0.9300
C19—C18	1.5243 (19)	N1—C15	1.3292 (18)
C19—H19A	0.9700	N1—C16	1.4560 (18)
C19—H19B	0.9700	N1—H1N1	0.8962
C3—C4	1.378 (2)	C15—C14	1.5077 (19)
C3—C2	1.393 (2)	C14—H14A	0.9700
C3—H3	0.9300	C14—H14B	0.9700
C5—C6	1.3880 (19)	C2—H2	0.9300
C5—C4	1.387 (2)	C17—C16	1.5171 (19)
C5—H5	0.9300	C17—H17A	0.9700
C11—C10	1.377 (2)	C17—H17B	0.9700
C11—C12	1.388 (2)	C16—H16A	0.9700
C11—H11	0.9300	C16—H16B	0.9700
C8—C9	1.3856 (19)

C1—O4—C19	117.00 (10)	C10—C9—H9	119.9
C13—O1—C14	117.60 (10)	C13—C12—C11	119.91 (13)
C18—N2—C17	121.67 (12)	C13—C12—H12	120.0
C18—N2—H1N2	116.0	C11—C12—H12	120.0
C17—N2—H1N2	122.3	C15—N1—C16	122.65 (11)
O4—C19—C18	111.17 (10)	C15—N1—H1N1	117.8
O4—C19—H19A	109.4	C16—N1—H1N1	117.7
C18—C19—H19A	109.4	O2—C15—N1	123.36 (12)
O4—C19—H19B	109.4	O2—C15—C14	120.06 (12)
C18—C19—H19B	109.4	N1—C15—C14	116.55 (11)
H19A—C19—H19B	108.0	O1—C14—C15	108.66 (10)
C4—C3—C2	118.92 (13)	O1—C14—H14A	110.0
C4—C3—H3	120.5	C15—C14—H14A	110.0
C2—C3—H3	120.5	O1—C14—H14B	110.0
C6—C5—C4	120.49 (13)	C15—C14—H14B	110.0
C6—C5—H5	119.8	H14A—C14—H14B	108.3
C4—C5—H5	119.8	O3—C18—N2	123.61 (13)
C10—C11—C12	118.92 (13)	O3—C18—C19	122.07 (12)
C10—C11—H11	120.5	N2—C18—C19	114.31 (12)
C12—C11—H11	120.5	C1—C2—C3	120.07 (13)
C9—C8—C13	118.00 (12)	C1—C2—H2	120.0
C9—C8—C7	121.76 (12)	C3—C2—H2	120.0
C13—C8—C7	120.24 (12)	C3—C4—C5	121.37 (12)
O4—C1—C2	123.97 (12)	C3—C4—Cl1	119.56 (11)
O4—C1—C6	115.20 (12)	C5—C4—Cl1	119.08 (11)
C2—C1—C6	120.83 (12)	N2—C17—C16	111.17 (11)
C5—C6—C1	118.23 (12)	N2—C17—H17A	109.4
C5—C6—C7	121.01 (12)	C16—C17—H17A	109.4
C1—C6—C7	120.75 (12)	N2—C17—H17B	109.4
C8—C7—C6	113.54 (11)	C16—C17—H17B	109.4
C8—C7—H7A	108.9	H17A—C17—H17B	108.0
C6—C7—H7A	108.9	C11—C10—C9	121.58 (13)
C8—C7—H7B	108.9	C11—C10—Cl2	118.62 (11)
C6—C7—H7B	108.9	C9—C10—Cl2	119.77 (11)
H7A—C7—H7B	107.7	N1—C16—C17	110.63 (11)
O1—C13—C12	123.54 (12)	N1—C16—H16A	109.5
O1—C13—C8	115.16 (11)	C17—C16—H16A	109.5
C12—C13—C8	121.29 (12)	N1—C16—H16B	109.5
C8—C9—C10	120.29 (12)	C17—C16—H16B	109.5
C8—C9—H9	119.9	H16A—C16—H16B	108.1

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.89	2.05	2.8945 (15)	158
C14—H14A···O3ⁱ	0.97	2.54	3.5026 (17)	172
C14—H14B···O3ⁱⁱ	0.97	2.34	3.2934 (17)	167
C16—H16B···O1ⁱⁱⁱ	0.97	2.59	3.2843 (17)	129
C19—H19A···Cl2^iv	0.97	2.81	3.6201 (14)	142
C9—H9···Cg1^v	0.93	2.88	3.8006 (14)	174
N1—H1N1···O1	0.90	2.16	2.5935 (15)	109

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈Cl₂N₂O₄
M_r	409.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	12.0877 (3), 8.73462 (15), 17.3712 (4)
β (°)	93.588 (2)
V (Å³)	1830.48 (7)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.44
Crystal size (mm)	0.31 × 0.22 × 0.21

Data collection
Diffractometer	Agilent Xcalibur Atlas Gemini ultra diffractometer
Absorption correction	Analytical (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.175, 0.342
No. of measured, independent and observed [I > 2σ(I)] reflections	19596, 3271, 3210
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.074, 1.07
No. of reflections	3271
No. of parameters	244
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.29

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

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2ⁱ	0.89	2.05	2.8945 (15)	158
C14—H14A···O3ⁱ	0.97	2.54	3.5026 (17)	172
C14—H14B···O3ⁱⁱ	0.97	2.34	3.2934 (17)	167
C16—H16B···O1ⁱⁱⁱ	0.97	2.59	3.2843 (17)	129
C19—H19A···Cl2^iv	0.97	2.81	3.6201 (14)	142
C9—H9···Cg1^v	0.93	2.88	3.8006 (14)	174
N1—H1N1···O1	0.90	2.16	2.5935 (15)	109

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

Acknowledgements

This study was supported financially by 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 ME09058).

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, 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
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Volume 68| Part 6| June 2012| Pages o1698-o1699

doi:10.1107/S1600536812020351

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

2,17-Di­chloro-8,9,10,11-tetra­hydro-19H-dibenzo[k,n][1,10,4,7]dioxadi­aza­cyclo­penta­decine-7,12(6H,13H)-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,17-Dichloro-8,9,10,11-tetrahydro-19H-dibenzo[k,n][1,10,4,7]dioxadiazacyclopentadecine-7,12(6H,13H)-dione