(5,6:19,20-Dibenzo-1,4,11,14-tetra­oxa-8,17-diaza­cyclo­eicosane-κ4N8,O11,O14,N17)dinitrato-κ4O,O′-cadmium(II)

Han, T.-T.; Ma, J.-F.; Zhang, L.-P.; Li, Q.-J.

doi:10.1107/S1600536807056541

(5,6:19,20-Dibenzo-1,4,11,14-tetraoxa-8,17-diazacycloeicosane-κ⁴N⁸,O¹¹,O¹⁴,N¹⁷)dinitrato-κ⁴O,O′-cadmium(II)

T.-T. Han, J.-F. Ma, L.-P. Zhang and Q.-J. Li

In the title compound, [Cd(NO₃)₂(C₂₂H₃₀N₂O₄)], the Cd^II atom is eight-coordinated by two amine N atoms and two O atoms from the 5,6:19,20-dibenzo-1,4,11,14-tetraoxa-8,17-diazacycloeicosane ligand and four O atoms from two nitrate groups. The coordination geometry about Cd is antiprismatic. One nitro O atom is disordered equally over two positions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056541/cs2056sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056541/cs2056Isup2.hkl Contains datablock I

CCDC reference: 677437

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R factor = 0.042
wR factor = 0.105
Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        O10
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         C7
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         C8

Alert level C
PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.68 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O8
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        O11
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Cd1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT793_ALERT_1_G Check the Absolute Configuration of N1     = ...          S
PLAT793_ALERT_1_G Check the Absolute Configuration of N2     = ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  12 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

In the last few decades, the modification of the macrocycles to control and tune the properties of coordinated metal atoms has been the subject of much interest (Meyerstein, 1990; Vicente et al., 2003). We are involved in studies of oxaaza-macrocycles and their metal coordination compounds. In this paper, we report the preparation and crystal structure of the title macrocyclic complex of Cd^II.

In the structure of the title compound, Cd^II is eight-coordinated by two N atoms and two O atoms from ligand L and four O atoms from two nitrate groups. The title compound displays an antiprismatic geometry (Fig. 1). The bond distances and angles around the Cd atom are nomal (Popović et al., 2006).

Related literature top

For related literature, see: López-Deber et al. (2005); Vicente et al. (2003); Meyerstein (1990); Popović et al. (2006).

Experimental top

Ligand L was synthesized according to the reported method (López-Deber et al., 2005). A solution of Cd(NO₃)₂.4H₂O (0.03 g, 0.10 mmol) in 5 ml e thanol was added dropwise to a solution of H₂L (0.039 g, 0.10 mmol) in 6 ml e thanol. After stirring for 30 min, the mixture was filtered. Colorless crystals were obtained by evaporating the filtrate at room temperature (yield 50%).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. A view of the molecule of I. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. Only one disorder site is shown for a nitrate.

[5,6:19,20-Dibenzo-1,4,11,14-tetraoxa-8,17-diazacycloeicosane- κ⁴N⁸,O¹¹,O¹⁴,N¹⁷]dinitrato-κ⁴O,O'-cadmium(II) top

Crystal data top

[Cd(NO₃)₂(C₂₂H₃₀N₂O₄)]	F(000) = 1272
M_r = 622.90	D_x = 1.625 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 3767 reflections
a = 13.167 (3) Å	θ = 1.6–25.2°
b = 7.6750 (15) Å	µ = 0.92 mm⁻¹
c = 25.227 (5) Å	T = 293 K
β = 92.568 (4)°	Block, colourless
V = 2546.8 (9) Å³	0.22 × 0.21 × 0.19 mm
Z = 4

Data collection top

Bruker APEX CCD area-detector diffractometer	4558 independent reflections
Radiation source: fine-focus sealed tube	3767 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ω scans	θ_max = 25.2°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
T_min = 0.82, T_max = 0.84	k = −9→8
12190 measured reflections	l = −30→23

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0554P)² + 0.8726P] where P = (F_o² + 2F_c²)/3
4558 reflections	(Δ/σ)_max < 0.001
349 parameters	Δρ_max = 1.00 e Å⁻³
1 restraint	Δρ_min = −1.00 e Å⁻³

Crystal data top

[Cd(NO₃)₂(C₂₂H₃₀N₂O₄)]	V = 2546.8 (9) Å³
M_r = 622.90	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.167 (3) Å	µ = 0.92 mm⁻¹
b = 7.6750 (15) Å	T = 293 K
c = 25.227 (5) Å	0.22 × 0.21 × 0.19 mm
β = 92.568 (4)°

Data collection top

Bruker APEX CCD area-detector diffractometer	4558 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3767 reflections with I > 2σ(I)
T_min = 0.82, T_max = 0.84	R_int = 0.056
12190 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 1.00 e Å⁻³
4558 reflections	Δρ_min = −1.00 e Å⁻³
349 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cd1	0.237559 (19)	0.06536 (3)	0.068001 (9)	0.03453 (12)
C1	0.3037 (3)	0.2975 (5)	0.26599 (15)	0.0463 (9)
C2	0.3327 (4)	0.3662 (6)	0.31505 (16)	0.0567 (11)
H2	0.2898	0.4418	0.3323	0.068*
C3	0.4250 (3)	0.3218 (6)	0.33784 (16)	0.0556 (11)
H3	0.4448	0.3669	0.3709	0.067*
C4	0.4888 (3)	0.2114 (6)	0.31257 (17)	0.0566 (11)
H4	0.5522	0.1839	0.3281	0.068*
C5	0.4585 (3)	0.1415 (5)	0.26411 (16)	0.0501 (10)
H5	0.5020	0.0665	0.2471	0.060*
C6	0.3642 (3)	0.1809 (5)	0.24025 (14)	0.0422 (9)
C7	0.1505 (5)	0.4558 (8)	0.2560 (3)	0.110 (3)
H7A	0.1873	0.5651	0.2544	0.132*
H7B	0.1373	0.4350	0.2930	0.132*
C8	0.0537 (3)	0.4785 (6)	0.22754 (19)	0.0597 (12)
H8A	0.0022	0.5032	0.2528	0.072*
H8B	0.0579	0.5785	0.2042	0.072*
C9	−0.0699 (3)	0.3258 (5)	0.17268 (16)	0.0460 (9)
C10	−0.1521 (3)	0.4239 (5)	0.18653 (18)	0.0552 (11)
H10	−0.1454	0.5067	0.2134	0.066*
C11	−0.2452 (3)	0.3972 (6)	0.15981 (19)	0.0587 (11)
H11	−0.3015	0.4611	0.1695	0.070*
C12	−0.2557 (3)	0.2788 (6)	0.11950 (17)	0.0550 (10)
H12	−0.3181	0.2642	0.1014	0.066*
C13	−0.1727 (3)	0.1810 (5)	0.10590 (16)	0.0479 (9)
H13	−0.1798	0.0994	0.0787	0.057*
C14	−0.0788 (3)	0.2032 (5)	0.13236 (14)	0.0414 (8)
C15	0.3261 (3)	0.0939 (5)	0.18976 (15)	0.0454 (9)
H15A	0.3732	0.0017	0.1814	0.054*
H15B	0.2612	0.0397	0.1960	0.054*
C16	0.0130 (3)	0.1004 (4)	0.11704 (16)	0.0412 (8)
H16A	0.0521	0.0678	0.1490	0.049*
H16B	−0.0097	−0.0059	0.0994	0.049*
C17	0.4099 (3)	0.2851 (5)	0.12706 (16)	0.0478 (9)
H17A	0.4557	0.1927	0.1173	0.057*
H17B	0.4415	0.3482	0.1567	0.057*
C18	0.3922 (4)	0.4067 (5)	0.08089 (18)	0.0577 (11)
H18A	0.3528	0.5068	0.0914	0.069*
H18B	0.4565	0.4476	0.0683	0.069*
C19	0.3169 (4)	0.4064 (5)	−0.00699 (17)	0.0543 (11)
H19A	0.3795	0.4405	−0.0230	0.065*
H19B	0.2782	0.5105	0.0003	0.065*
C20	0.2563 (3)	0.2872 (6)	−0.04333 (15)	0.0541 (10)
H20A	0.2293	0.3534	−0.0735	0.065*
H20B	0.3008	0.1979	−0.0565	0.065*
C21	0.0930 (3)	0.3238 (5)	−0.00682 (16)	0.0474 (9)
H21A	0.0550	0.3526	−0.0395	0.057*
H21B	0.1202	0.4308	0.0086	0.057*
C22	0.0255 (3)	0.2383 (5)	0.03056 (15)	0.0445 (9)
H22A	−0.0314	0.3145	0.0370	0.053*
H22B	−0.0012	0.1316	0.0148	0.053*
N1	0.3131 (2)	0.2088 (4)	0.14301 (11)	0.0380 (7)
N2	0.0799 (2)	0.1973 (4)	0.08151 (12)	0.0362 (7)
N3	0.1614 (3)	−0.2792 (4)	0.09950 (14)	0.0510 (8)
N4	0.3934 (3)	−0.1361 (4)	0.02528 (15)	0.0504 (8)
O1	0.2109 (2)	0.3313 (4)	0.24031 (13)	0.0725 (10)
O2	0.0240 (2)	0.3344 (4)	0.19770 (14)	0.0711 (10)
O3	0.3384 (2)	0.3117 (3)	0.04042 (10)	0.0510 (7)
O4	0.1745 (2)	0.2061 (3)	−0.01765 (9)	0.0444 (6)
O5	0.3898 (3)	−0.1102 (5)	0.07408 (14)	0.0717 (9)
O6	0.3226 (3)	−0.0730 (4)	−0.00288 (13)	0.0649 (9)
O7	0.4605 (3)	−0.2216 (5)	0.00709 (18)	0.0926 (12)
O8	0.1473 (3)	−0.2092 (4)	0.05524 (13)	0.0673 (8)
O9	0.1617 (10)	−0.439 (3)	0.1075 (11)	0.067 (4)	0.50
O10	0.1959 (3)	−0.1895 (4)	0.13589 (14)	0.0847 (11)
O11	0.1198 (10)	−0.424 (3)	0.1043 (11)	0.075 (4)	0.50
H1N	0.272 (4)	0.298 (7)	0.150 (2)	0.090*
H2N	0.098 (4)	0.287 (8)	0.096 (2)	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.04017 (18)	0.02992 (17)	0.03375 (17)	0.00307 (10)	0.00432 (12)	−0.00144 (9)
C1	0.049 (2)	0.047 (2)	0.043 (2)	−0.0025 (18)	0.0002 (18)	−0.0047 (17)
C2	0.070 (3)	0.055 (2)	0.045 (2)	−0.006 (2)	0.001 (2)	−0.0145 (19)
C3	0.067 (3)	0.062 (3)	0.037 (2)	−0.019 (2)	−0.004 (2)	−0.0040 (19)
C4	0.061 (3)	0.052 (2)	0.055 (2)	−0.013 (2)	−0.015 (2)	0.011 (2)
C5	0.056 (2)	0.043 (2)	0.051 (2)	0.0012 (19)	0.000 (2)	0.0005 (17)
C6	0.054 (2)	0.0334 (19)	0.0387 (19)	−0.0028 (17)	−0.0029 (18)	−0.0004 (15)
C7	0.088 (4)	0.077 (4)	0.160 (6)	0.035 (3)	−0.051 (4)	−0.068 (4)
C8	0.069 (3)	0.045 (2)	0.065 (3)	0.012 (2)	−0.002 (2)	−0.021 (2)
C9	0.049 (2)	0.040 (2)	0.049 (2)	0.0082 (18)	0.0055 (19)	−0.0021 (17)
C10	0.058 (3)	0.051 (2)	0.057 (3)	0.014 (2)	0.010 (2)	−0.0077 (19)
C11	0.052 (3)	0.058 (3)	0.068 (3)	0.020 (2)	0.015 (2)	0.003 (2)
C12	0.045 (2)	0.060 (3)	0.060 (3)	0.003 (2)	0.008 (2)	0.004 (2)
C13	0.047 (2)	0.046 (2)	0.051 (2)	−0.0023 (18)	0.0070 (19)	−0.0009 (17)
C14	0.045 (2)	0.0354 (19)	0.044 (2)	0.0011 (16)	0.0102 (17)	0.0007 (16)
C15	0.058 (2)	0.036 (2)	0.041 (2)	0.0021 (17)	−0.0024 (19)	−0.0043 (15)
C16	0.047 (2)	0.0306 (18)	0.046 (2)	0.0049 (16)	0.0073 (18)	−0.0012 (15)
C17	0.043 (2)	0.050 (2)	0.050 (2)	−0.0066 (18)	0.0027 (18)	−0.0054 (18)
C18	0.067 (3)	0.048 (2)	0.057 (3)	−0.013 (2)	0.003 (2)	0.0000 (19)
C19	0.055 (2)	0.057 (3)	0.052 (2)	−0.002 (2)	0.020 (2)	0.0180 (19)
C20	0.063 (3)	0.063 (3)	0.038 (2)	0.006 (2)	0.0227 (19)	0.0073 (19)
C21	0.056 (2)	0.039 (2)	0.047 (2)	0.0117 (18)	−0.0001 (19)	0.0057 (17)
C22	0.047 (2)	0.037 (2)	0.050 (2)	0.0064 (17)	−0.0003 (18)	0.0011 (16)
N1	0.0424 (17)	0.0356 (16)	0.0361 (16)	0.0006 (13)	0.0027 (14)	−0.0016 (13)
N2	0.0402 (16)	0.0287 (15)	0.0401 (16)	0.0027 (13)	0.0037 (13)	−0.0051 (12)
N3	0.064 (2)	0.0343 (18)	0.055 (2)	−0.0062 (17)	0.0082 (18)	−0.0069 (16)
N4	0.051 (2)	0.0383 (18)	0.063 (2)	0.0029 (16)	0.0114 (18)	−0.0043 (16)
O1	0.0618 (19)	0.079 (2)	0.074 (2)	0.0264 (17)	−0.0188 (17)	−0.0395 (18)
O2	0.0611 (19)	0.0554 (19)	0.095 (2)	0.0182 (15)	−0.0221 (18)	−0.0349 (17)
O3	0.0648 (18)	0.0436 (15)	0.0444 (14)	−0.0110 (13)	0.0024 (13)	0.0079 (12)
O4	0.0554 (16)	0.0399 (14)	0.0385 (13)	0.0078 (12)	0.0076 (12)	−0.0001 (11)
O5	0.076 (2)	0.074 (2)	0.063 (2)	0.0211 (18)	−0.0111 (19)	−0.0101 (17)
O6	0.071 (2)	0.065 (2)	0.0579 (19)	0.0131 (16)	−0.0053 (17)	−0.0043 (14)
O7	0.075 (2)	0.071 (2)	0.135 (3)	0.0246 (19)	0.044 (2)	−0.018 (2)
O8	0.079 (2)	0.0600 (19)	0.0618 (19)	−0.0019 (16)	−0.0068 (17)	0.0067 (16)
O9	0.076 (9)	0.036 (5)	0.091 (7)	−0.017 (8)	0.008 (9)	−0.002 (4)
O10	0.122 (3)	0.054 (2)	0.075 (2)	−0.0126 (19)	−0.023 (2)	−0.0153 (17)
O11	0.090 (11)	0.048 (7)	0.087 (7)	−0.031 (9)	0.006 (11)	−0.004 (5)

Geometric parameters (Å, º) top

Cd1—N2	2.348 (3)	C14—C16	1.508 (5)
Cd1—N1	2.369 (3)	C15—N1	1.476 (5)
Cd1—O6	2.399 (3)	C15—H15A	0.9700
Cd1—O5	2.415 (3)	C15—H15B	0.9700
Cd1—O3	2.430 (3)	C16—N2	1.484 (5)
Cd1—O8	2.433 (3)	C16—H16A	0.9700
Cd1—O4	2.523 (2)	C16—H16B	0.9700
Cd1—O10	2.673 (2)	C17—N1	1.475 (5)
C1—C6	1.380 (5)	C17—C18	1.503 (6)
C1—O1	1.382 (5)	C17—H17A	0.9700
C1—C2	1.383 (5)	C17—H17B	0.9700
C2—C3	1.364 (6)	C18—O3	1.418 (5)
C2—H2	0.9300	C18—H18A	0.9700
C3—C4	1.370 (6)	C18—H18B	0.9700
C3—H3	0.9300	C19—O3	1.417 (5)
C4—C5	1.378 (6)	C19—C20	1.499 (6)
C4—H4	0.9300	C19—H19A	0.9700
C5—C6	1.389 (5)	C19—H19B	0.9700
C5—H5	0.9300	C20—O4	1.425 (5)
C6—C15	1.504 (5)	C20—H20A	0.9700
C7—O1	1.315 (6)	C20—H20B	0.9700
C7—C8	1.445 (6)	C21—O4	1.439 (4)
C7—H7A	0.9700	C21—C22	1.477 (6)
C7—H7B	0.9700	C21—H21A	0.9700
C8—O2	1.384 (5)	C21—H21B	0.9700
C8—H8A	0.9700	C22—N2	1.477 (5)
C8—H8B	0.9700	C22—H22A	0.9700
C9—O2	1.364 (5)	C22—H22B	0.9700
C9—C10	1.377 (6)	N1—H1N	0.90 (6)
C9—C14	1.387 (5)	N2—H2N	0.81 (6)
C10—C11	1.387 (6)	N3—O10	1.219 (4)
C10—H10	0.9300	N3—O9	1.24 (2)
C11—C12	1.366 (6)	N3—O8	1.245 (4)
C11—H11	0.9300	N3—O11	1.25 (2)
C12—C13	1.381 (6)	N4—O7	1.207 (4)
C12—H12	0.9300	N4—O6	1.245 (4)
C13—C14	1.389 (5)	N4—O5	1.250 (5)
C13—H13	0.9300	O9—O11	0.57 (2)

N2—Cd1—N1	91.47 (10)	N2—C16—C14	113.4 (3)
N2—Cd1—O6	138.07 (10)	N2—C16—H16A	108.9
N1—Cd1—O6	127.43 (11)	C14—C16—H16A	108.9
N2—Cd1—O5	165.52 (12)	N2—C16—H16B	108.9
N1—Cd1—O5	83.75 (11)	C14—C16—H16B	108.9
O6—Cd1—O5	52.16 (11)	H16A—C16—H16B	107.7
N2—Cd1—O3	101.75 (10)	N1—C17—C18	110.6 (3)
N1—Cd1—O3	69.64 (10)	N1—C17—H17A	109.5
O6—Cd1—O3	81.48 (10)	C18—C17—H17A	109.5
O5—Cd1—O3	89.42 (12)	N1—C17—H17B	109.5
N2—Cd1—O8	87.88 (11)	C18—C17—H17B	109.5
N1—Cd1—O8	133.87 (10)	H17A—C17—H17B	108.1
O6—Cd1—O8	76.09 (12)	O3—C18—C17	107.1 (3)
O5—Cd1—O8	85.66 (11)	O3—C18—H18A	110.3
O3—Cd1—O8	154.93 (10)	C17—C18—H18A	110.3
N2—Cd1—O4	71.36 (9)	O3—C18—H18B	110.3
N1—Cd1—O4	126.54 (10)	C17—C18—H18B	110.3
O6—Cd1—O4	72.42 (9)	H18A—C18—H18B	108.6
O5—Cd1—O4	122.27 (10)	O3—C19—C20	106.5 (3)
O3—Cd1—O4	65.46 (8)	O3—C19—H19A	110.4
O8—Cd1—O4	96.74 (9)	C20—C19—H19A	110.4
C6—C1—O1	114.7 (3)	O3—C19—H19B	110.4
C6—C1—C2	121.8 (4)	C20—C19—H19B	110.4
O1—C1—C2	123.4 (4)	H19A—C19—H19B	108.6
C3—C2—C1	119.1 (4)	O4—C20—C19	112.4 (3)
C3—C2—H2	120.4	O4—C20—H20A	109.1
C1—C2—H2	120.4	C19—C20—H20A	109.1
C2—C3—C4	120.8 (4)	O4—C20—H20B	109.1
C2—C3—H3	119.6	C19—C20—H20B	109.1
C4—C3—H3	119.6	H20A—C20—H20B	107.9
C3—C4—C5	119.6 (4)	O4—C21—C22	108.5 (3)
C3—C4—H4	120.2	O4—C21—H21A	110.0
C5—C4—H4	120.2	C22—C21—H21A	110.0
C4—C5—C6	121.1 (4)	O4—C21—H21B	110.0
C4—C5—H5	119.4	C22—C21—H21B	110.0
C6—C5—H5	119.4	H21A—C21—H21B	108.4
C1—C6—C5	117.5 (3)	N2—C22—C21	111.6 (3)
C1—C6—C15	120.6 (3)	N2—C22—H22A	109.3
C5—C6—C15	121.9 (4)	C21—C22—H22A	109.3
O1—C7—C8	118.0 (4)	N2—C22—H22B	109.3
O1—C7—H7A	107.8	C21—C22—H22B	109.3
C8—C7—H7A	107.8	H22A—C22—H22B	108.0
O1—C7—H7B	107.8	C17—N1—C15	112.6 (3)
C8—C7—H7B	107.8	C17—N1—Cd1	107.7 (2)
H7A—C7—H7B	107.1	C15—N1—Cd1	113.0 (2)
O2—C8—C7	113.3 (4)	C17—N1—H1N	107 (4)
O2—C8—H8A	108.9	C15—N1—H1N	110 (4)
C7—C8—H8A	108.9	Cd1—N1—H1N	106 (3)
O2—C8—H8B	108.9	C22—N2—C16	110.8 (3)
C7—C8—H8B	108.9	C22—N2—Cd1	111.3 (2)
H8A—C8—H8B	107.7	C16—N2—Cd1	115.1 (2)
O2—C9—C10	124.3 (4)	C22—N2—H2N	110 (4)
O2—C9—C14	114.7 (3)	C16—N2—H2N	109 (4)
C10—C9—C14	121.0 (4)	Cd1—N2—H2N	101 (4)
C9—C10—C11	118.9 (4)	O10—N3—O9	115.9 (12)
C9—C10—H10	120.5	O10—N3—O8	117.9 (3)
C11—C10—H10	120.5	O9—N3—O8	124.8 (13)
C12—C11—C10	121.1 (4)	O10—N3—O11	125.5 (13)
C12—C11—H11	119.4	O8—N3—O11	115.0 (12)
C10—C11—H11	119.4	O7—N4—O6	122.5 (4)
C11—C12—C13	119.5 (4)	O7—N4—O5	121.5 (4)
C11—C12—H12	120.3	O6—N4—O5	116.0 (4)
C13—C12—H12	120.3	C7—O1—C1	121.9 (3)
C12—C13—C14	120.7 (4)	C9—O2—C8	121.2 (3)
C12—C13—H13	119.6	C19—O3—C18	114.7 (3)
C14—C13—H13	119.6	C19—O3—Cd1	123.4 (2)
C9—C14—C13	118.7 (4)	C18—O3—Cd1	117.1 (2)
C9—C14—C16	120.0 (3)	C20—O4—C21	113.4 (3)
C13—C14—C16	121.3 (3)	C20—O4—Cd1	110.5 (2)
N1—C15—C6	115.7 (3)	C21—O4—Cd1	109.0 (2)
N1—C15—H15A	108.4	N4—O5—Cd1	95.4 (2)
C6—C15—H15A	108.4	N4—O6—Cd1	96.3 (2)
N1—C15—H15B	108.4	N3—O8—Cd1	101.7 (2)
C6—C15—H15B	108.4	O11—O9—N3	77 (5)
H15A—C15—H15B	107.4	O9—O11—N3	77 (4)

C6—C1—C2—C3	2.1 (7)	C10—C9—O2—C8	−20.9 (7)
O1—C1—C2—C3	178.4 (4)	C14—C9—O2—C8	161.5 (4)
C1—C2—C3—C4	0.4 (7)	C7—C8—O2—C9	173.2 (6)
C2—C3—C4—C5	−1.4 (7)	C20—C19—O3—C18	−177.5 (3)
C3—C4—C5—C6	0.0 (6)	C20—C19—O3—Cd1	−22.8 (4)
O1—C1—C6—C5	−180.0 (4)	C17—C18—O3—C19	−178.7 (4)
C2—C1—C6—C5	−3.4 (6)	C17—C18—O3—Cd1	24.9 (4)
O1—C1—C6—C15	−3.1 (6)	N2—Cd1—O3—C19	−64.3 (3)
C2—C1—C6—C15	173.5 (4)	N1—Cd1—O3—C19	−151.5 (3)
C4—C5—C6—C1	2.3 (6)	O6—Cd1—O3—C19	73.2 (3)
C4—C5—C6—C15	−174.6 (4)	O5—Cd1—O3—C19	125.0 (3)
O1—C7—C8—O2	18.3 (10)	O8—Cd1—O3—C19	46.5 (4)
O2—C9—C10—C11	−176.8 (4)	O4—Cd1—O3—C19	−1.3 (3)
C14—C9—C10—C11	0.7 (7)	N2—Cd1—O3—C18	89.8 (3)
C9—C10—C11—C12	−1.5 (7)	N1—Cd1—O3—C18	2.7 (3)
C10—C11—C12—C13	1.5 (7)	O6—Cd1—O3—C18	−132.7 (3)
C11—C12—C13—C14	−0.7 (6)	O5—Cd1—O3—C18	−80.9 (3)
O2—C9—C14—C13	177.8 (4)	O8—Cd1—O3—C18	−159.3 (3)
C10—C9—C14—C13	0.1 (6)	O4—Cd1—O3—C18	152.8 (3)
O2—C9—C14—C16	−3.8 (5)	C19—C20—O4—C21	71.5 (4)
C10—C9—C14—C16	178.5 (4)	C19—C20—O4—Cd1	−51.3 (4)
C12—C13—C14—C9	−0.1 (6)	C22—C21—O4—C20	−166.5 (3)
C12—C13—C14—C16	−178.5 (4)	C22—C21—O4—Cd1	−43.0 (3)
C1—C6—C15—N1	68.8 (5)	N2—Cd1—O4—C20	140.1 (2)
C5—C6—C15—N1	−114.5 (4)	N1—Cd1—O4—C20	62.6 (3)
C9—C14—C16—N2	−80.7 (4)	O6—Cd1—O4—C20	−61.4 (2)
C13—C14—C16—N2	97.7 (4)	O5—Cd1—O4—C20	−45.4 (3)
N1—C17—C18—O3	−54.4 (5)	O3—Cd1—O4—C20	27.1 (2)
O3—C19—C20—O4	48.3 (5)	O8—Cd1—O4—C20	−134.5 (2)
O4—C21—C22—N2	61.4 (4)	N2—Cd1—O4—C21	14.8 (2)
C18—C17—N1—C15	−177.6 (3)	N1—Cd1—O4—C21	−62.7 (2)
C18—C17—N1—Cd1	57.3 (3)	O6—Cd1—O4—C21	173.3 (2)
C6—C15—N1—C17	63.5 (4)	O5—Cd1—O4—C21	−170.7 (2)
C6—C15—N1—Cd1	−174.3 (3)	O3—Cd1—O4—C21	−98.2 (2)
N2—Cd1—N1—C17	−132.3 (2)	O8—Cd1—O4—C21	100.2 (2)
O6—Cd1—N1—C17	30.8 (3)	O7—N4—O5—Cd1	179.6 (4)
O5—Cd1—N1—C17	61.4 (2)	O6—N4—O5—Cd1	−2.4 (4)
O3—Cd1—N1—C17	−30.3 (2)	N2—Cd1—O5—N4	140.9 (4)
O8—Cd1—N1—C17	139.2 (2)	N1—Cd1—O5—N4	−147.8 (3)
O4—Cd1—N1—C17	−64.6 (3)	O6—Cd1—O5—N4	1.4 (2)
N2—Cd1—N1—C15	102.8 (3)	O3—Cd1—O5—N4	−78.2 (3)
O6—Cd1—N1—C15	−94.1 (3)	O8—Cd1—O5—N4	77.1 (3)
O5—Cd1—N1—C15	−63.5 (3)	O4—Cd1—O5—N4	−18.1 (3)
O3—Cd1—N1—C15	−155.2 (3)	O7—N4—O6—Cd1	−179.6 (4)
O8—Cd1—N1—C15	14.3 (3)	O5—N4—O6—Cd1	2.4 (4)
O4—Cd1—N1—C15	170.5 (2)	N2—Cd1—O6—N4	−167.3 (2)
C21—C22—N2—C16	−176.0 (3)	N1—Cd1—O6—N4	38.4 (3)
C21—C22—N2—Cd1	−46.6 (3)	O5—Cd1—O6—N4	−1.4 (2)
C14—C16—N2—C22	−62.8 (4)	O3—Cd1—O6—N4	94.5 (2)
C14—C16—N2—Cd1	169.9 (2)	O8—Cd1—O6—N4	−96.8 (2)
N1—Cd1—N2—C22	144.3 (2)	O4—Cd1—O6—N4	161.4 (2)
O6—Cd1—N2—C22	−15.5 (3)	O10—N3—O8—Cd1	12.1 (4)
O5—Cd1—N2—C22	−145.3 (4)	O9—N3—O8—Cd1	−153.4 (9)
O3—Cd1—N2—C22	74.8 (2)	O11—N3—O8—Cd1	178.3 (10)
O8—Cd1—N2—C22	−81.9 (2)	N2—Cd1—O8—N3	−99.4 (3)
O4—Cd1—N2—C22	16.0 (2)	N1—Cd1—O8—N3	−9.4 (3)
N1—Cd1—N2—C16	−88.7 (2)	O6—Cd1—O8—N3	119.7 (3)
O6—Cd1—N2—C16	111.5 (2)	O5—Cd1—O8—N3	67.6 (3)
O5—Cd1—N2—C16	−18.3 (5)	O3—Cd1—O8—N3	146.9 (3)
O3—Cd1—N2—C16	−158.2 (2)	O4—Cd1—O8—N3	−170.4 (3)
O8—Cd1—N2—C16	45.2 (2)	O10—N3—O9—O11	118 (5)
O4—Cd1—N2—C16	143.0 (2)	O8—N3—O9—O11	−76 (6)
C8—C7—O1—C1	−178.4 (5)	O10—N3—O11—O9	−76 (6)
C6—C1—O1—C7	−170.9 (6)	O8—N3—O11—O9	118 (5)
C2—C1—O1—C7	12.6 (8)

Experimental details

Crystal data
Chemical formula	[Cd(NO₃)₂(C₂₂H₃₀N₂O₄)]
M_r	622.90
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.167 (3), 7.6750 (15), 25.227 (5)
β (°)	92.568 (4)
V (Å³)	2546.8 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.92
Crystal size (mm)	0.22 × 0.21 × 0.19

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.82, 0.84
No. of measured, independent and observed [I > 2σ(I)] reflections	12190, 4558, 3767
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.105, 1.04
No. of reflections	4558
No. of parameters	349
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.00, −1.00

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).

Selected geometric parameters (Å, º) top

Cd1—N2	2.348 (3)	Cd1—O3	2.430 (3)
Cd1—N1	2.369 (3)	Cd1—O8	2.433 (3)
Cd1—O6	2.399 (3)	Cd1—O4	2.523 (2)
Cd1—O5	2.415 (3)	Cd1—O10	2.673 (2)

N2—Cd1—N1	91.47 (10)	N1—Cd1—O8	133.87 (10)
N2—Cd1—O6	138.07 (10)	O6—Cd1—O8	76.09 (12)
N1—Cd1—O6	127.43 (11)	O5—Cd1—O8	85.66 (11)
N2—Cd1—O5	165.52 (12)	O3—Cd1—O8	154.93 (10)
N1—Cd1—O5	83.75 (11)	N2—Cd1—O4	71.36 (9)
O6—Cd1—O5	52.16 (11)	N1—Cd1—O4	126.54 (10)
N2—Cd1—O3	101.75 (10)	O6—Cd1—O4	72.42 (9)
N1—Cd1—O3	69.64 (10)	O5—Cd1—O4	122.27 (10)
O6—Cd1—O3	81.48 (10)	O3—Cd1—O4	65.46 (8)
O5—Cd1—O3	89.42 (12)	O8—Cd1—O4	96.74 (9)
N2—Cd1—O8	87.88 (11)

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(5,6:19,20-Dibenzo-1,4,11,14-tetra­oxa-8,17-diaza­cyclo­eicosane-κ4N8,O11,O14,N17)dinitrato-κ4O,O′-cadmium(II)

Supporting information

Key indicators

checkCIF/PLATON results

(5,6:19,20-Dibenzo-1,4,11,14-tetraoxa-8,17-diazacycloeicosane-κ⁴N⁸,O¹¹,O¹⁴,N¹⁷)dinitrato-κ⁴O,O′-cadmium(II)