Bis[1,3-bis­(1H-benzimidazol-2-yl)­benzene-κN3]bis­(nitrato-κ2O,O′)­cadmium(II) dihydrate

Meng, F.-Y.; Zhang, Y.-M.; Ng, S.W.

doi:10.1107/S1600536807050210

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Bis[1,3-bis(1H-benzimidazol-2-yl)benzene-κN³]bis(nitrato-κ²O,O′)cadmium(II) dihydrate

F.-Y. Meng, Y.-M. Zhang and S. W. Ng

In the title complex, [Cd(NO₃)₂(C₂₀H₁₄N₄)₂]·2H₂O, the Cd^II ion, which lies on a crystallographic twofold axis, is bis-chelated by two nitrate ligands and is coordinated by one tertiary N atom from each of two 1,3-bis(1H-benzimidazol-2-ylmethyl)benzene ligands in a distorted octahedral geometry. In the crystal structure, complex molecules and solvent water molecules are connected via hydrogen bonds to form a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050210/lh2532sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050210/lh2532Isup2.hkl Contains datablock I

CCDC reference: 667177

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.035
wR factor = 0.111
Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O1     -   N5      ..      11.87 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O2     -   N5      ..      13.54 su

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        100 Ang.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cd1    -   O1      ..       9.80 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Cd1    -   O2      ..       8.14 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N5

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Cd1         (2)       2.25

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

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

Comment top

We have reported the zinc terephthalate and zinc succinate adducts of 1,3-bis(benzimidazol-2-ylmethyl)benzene, an N-heterocycle that is capable of binding through two nitrogen sites (Meng, Dong & Ng, 2007; Meng, Liu & Ng, 2007). In the title cadmium nitrate adduct, the two ligands bind in a unidentate manner as the two nitrate groups are chelated to the metal (see Fig. 1). The Lewis-basic amino sites of the molecule engage in hydrogen bonding interactions with the lattice water molecule to furnish a three-dimensional network structure.

Related literature top

For the structure of the related adduct of 1,3-bis(benzimidazol-2-ylmethyl)benzene with zinc terephthalate, see Meng, Liu & Ng (2007), and for the zinc succinate adduct, see Meng, Dong & Ng (2007). For the synthesis of 1,3-bis(benzimidazol-2-ylmethyl)benzene, see Chawla & Gill (1997).

Experimental top

1,3-Bis(benzimidazol-2-ylmethyl)benzene was prepared according to a reported procedure (Chawla & Gill, 1997). Cadmium nitrate tetrahydrate (0.08 g, 0.25 mmol), 1,3-bis(benzimidazol-2-ylmethyl)benzene (0.15 g, 0.5 mmol), ethanol (2 ml) and water (15 ml) were placed in a 23-ml, Teflon-lined, stainless -steel Parr bomb. The bomb was heated at 433 K for 5 days and cooled to room temperature at 5 K h^-1. Colorless crystals were obtained in 10% yield. A somewhat large block was used in the diffraction measurements.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top

Fig. 1. The molecular structure with displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. [Symmery code (i): –x, y, 1/2 – z.]

Bis[1,3-bis(1H-benzimidazol-2-yl)benzene-κN³]bis(nitrato- κ²O,O')cadmium(II) dihydrate top

Crystal data top

[Cd(NO₃)₂(C₂₀H₁₄N₄)₂]·2H₂O	F(000) = 1816
M_r = 893.16	D_x = 1.465 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 5514 reflections
a = 14.359 (1) Å	θ = 2.7–27.6°
b = 16.809 (1) Å	µ = 0.60 mm⁻¹
c = 16.780 (1) Å	T = 293 K
V = 4049.8 (5) Å³	Block, colorless
Z = 4	0.49 × 0.36 × 0.25 mm

Data collection top

Bruker APEXII area-detector diffractometer	4651 independent reflections
Radiation source: fine-focus sealed tube	3699 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 27.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
T_min = 0.735, T_max = 0.863	k = −21→21
33964 measured reflections	l = −21→21

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0609P)² + 3.0327P] where P = (F_o² + 2F_c²)/3
4651 reflections	(Δ/σ)_max = 0.001
267 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Cd(NO₃)₂(C₂₀H₁₄N₄)₂]·2H₂O	V = 4049.8 (5) Å³
M_r = 893.16	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 14.359 (1) Å	µ = 0.60 mm⁻¹
b = 16.809 (1) Å	T = 293 K
c = 16.780 (1) Å	0.49 × 0.36 × 0.25 mm

Data collection top

Bruker APEXII area-detector diffractometer	4651 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3699 reflections with I > 2σ(I)
T_min = 0.735, T_max = 0.863	R_int = 0.026
33964 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.01	Δρ_max = 0.40 e Å⁻³
4651 reflections	Δρ_min = −0.59 e Å⁻³
267 parameters

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

	x	y	z	U_iso*/U_eq
Cd1	0.0000	0.812267 (14)	0.2500	0.04011 (10)
O1	−0.06502 (14)	0.86543 (10)	0.36422 (11)	0.0525 (5)
O2	−0.11506 (18)	0.91958 (13)	0.25262 (11)	0.0589 (5)
O3	−0.1546 (3)	0.9858 (2)	0.3759 (2)	0.1299 (13)
O4	0.23158 (19)	0.46184 (12)	0.35459 (15)	0.0817 (8)
H1W	0.2820	0.4507	0.3332	0.098*
H2W	0.2029	0.4217	0.3686	0.098*
N1	0.10316 (14)	0.72662 (11)	0.30585 (11)	0.0385 (4)
N2	0.15475 (15)	0.60964 (12)	0.34838 (12)	0.0442 (5)
H2n	0.1704	0.5602	0.3479	0.053*
N3	0.09189 (15)	0.76740 (12)	−0.00421 (12)	0.0447 (5)
H3n	0.0810	0.7946	0.0382	0.054*
N4	0.12082 (18)	0.66241 (14)	−0.08129 (13)	0.0516 (5)
N5	−0.11018 (19)	0.91902 (15)	0.32757 (18)	0.0629 (7)
C1	0.12630 (16)	0.73325 (14)	0.38599 (14)	0.0394 (5)
C2	0.1238 (2)	0.79860 (17)	0.43769 (16)	0.0495 (6)
H2	0.1043	0.8485	0.4204	0.059*
C3	0.1513 (2)	0.78597 (19)	0.51496 (17)	0.0579 (7)
H3	0.1502	0.8284	0.5505	0.069*
C4	0.1808 (2)	0.7120 (2)	0.54192 (17)	0.0637 (8)
H4	0.1980	0.7060	0.5950	0.076*
C5	0.1852 (2)	0.64744 (19)	0.49195 (16)	0.0571 (7)
H5	0.2053	0.5980	0.5098	0.069*
C6	0.15785 (17)	0.65970 (15)	0.41296 (15)	0.0422 (5)
C7	0.12274 (16)	0.65194 (14)	0.28564 (14)	0.0381 (5)
C8	0.11145 (17)	0.61731 (14)	0.20567 (14)	0.0397 (5)
C9	0.09638 (18)	0.53648 (15)	0.19548 (16)	0.0465 (6)
H9	0.0941	0.5031	0.2396	0.056*
C10	0.0848 (2)	0.50543 (16)	0.11971 (17)	0.0520 (6)
H10	0.0746	0.4512	0.1133	0.062*
C11	0.08827 (19)	0.55436 (16)	0.05356 (16)	0.0494 (6)
H11	0.0806	0.5329	0.0029	0.059*
C12	0.10332 (17)	0.63595 (15)	0.06270 (15)	0.0418 (5)
C13	0.11557 (18)	0.66654 (15)	0.13896 (14)	0.0404 (5)
H13	0.1267	0.7207	0.1455	0.048*
C14	0.10567 (18)	0.68767 (14)	−0.00786 (15)	0.0428 (5)
C15	0.1167 (2)	0.73083 (17)	−0.12796 (16)	0.0507 (6)
C16	0.1305 (3)	0.7409 (2)	−0.21018 (18)	0.0707 (9)
H16	0.1434	0.6978	−0.2432	0.085*
C17	0.1241 (4)	0.8167 (2)	−0.23986 (19)	0.0782 (12)
H17	0.1330	0.8249	−0.2941	0.094*
C18	0.1049 (2)	0.8813 (2)	−0.1919 (2)	0.0689 (9)
H18	0.1010	0.9316	−0.2148	0.083*
C19	0.0915 (2)	0.87329 (18)	−0.11142 (18)	0.0587 (7)
H19	0.0784	0.9169	−0.0792	0.070*
C20	0.09844 (19)	0.79700 (16)	−0.08038 (15)	0.0461 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.05074 (17)	0.03035 (15)	0.03923 (16)	0.000	−0.00704 (10)	0.000
O1	0.0681 (12)	0.0402 (9)	0.0492 (10)	0.0111 (9)	−0.0009 (9)	0.0097 (8)
O2	0.0788 (15)	0.0489 (11)	0.0491 (11)	0.0134 (10)	−0.0123 (9)	0.0037 (8)
O3	0.155 (3)	0.110 (2)	0.126 (3)	0.045 (2)	0.046 (2)	0.003 (2)
O4	0.0975 (18)	0.0449 (11)	0.1028 (19)	0.0213 (11)	0.0434 (15)	0.0257 (12)
N1	0.0452 (11)	0.0350 (10)	0.0354 (10)	0.0008 (8)	−0.0050 (8)	0.0005 (8)
N2	0.0534 (12)	0.0371 (10)	0.0421 (11)	0.0076 (9)	0.0022 (9)	0.0071 (9)
N3	0.0537 (12)	0.0446 (11)	0.0359 (10)	0.0004 (10)	0.0009 (9)	−0.0019 (9)
N4	0.0656 (15)	0.0520 (13)	0.0373 (11)	0.0026 (11)	0.0037 (10)	−0.0036 (10)
N5	0.0662 (16)	0.0482 (13)	0.0744 (18)	−0.0002 (12)	0.0051 (13)	0.0069 (12)
C1	0.0377 (12)	0.0433 (13)	0.0373 (12)	−0.0023 (10)	−0.0029 (9)	0.0026 (10)
C2	0.0521 (15)	0.0494 (14)	0.0471 (14)	−0.0016 (12)	−0.0066 (12)	−0.0045 (11)
C3	0.0591 (17)	0.0701 (19)	0.0445 (15)	−0.0026 (15)	−0.0054 (13)	−0.0129 (14)
C4	0.0650 (19)	0.091 (2)	0.0356 (14)	−0.0044 (17)	−0.0078 (13)	0.0055 (15)
C5	0.0619 (17)	0.0670 (18)	0.0424 (14)	0.0025 (14)	−0.0019 (12)	0.0190 (13)
C6	0.0414 (13)	0.0466 (13)	0.0388 (12)	0.0005 (11)	0.0011 (10)	0.0068 (10)
C7	0.0394 (12)	0.0364 (12)	0.0385 (12)	0.0013 (9)	0.0023 (9)	0.0042 (10)
C8	0.0409 (12)	0.0367 (12)	0.0416 (13)	0.0033 (9)	0.0022 (10)	−0.0018 (10)
C9	0.0526 (14)	0.0371 (12)	0.0497 (14)	0.0020 (11)	0.0061 (12)	0.0029 (11)
C10	0.0632 (17)	0.0368 (13)	0.0560 (16)	−0.0061 (12)	0.0062 (13)	−0.0087 (11)
C11	0.0578 (15)	0.0448 (14)	0.0454 (14)	−0.0062 (12)	0.0049 (12)	−0.0093 (11)
C12	0.0424 (13)	0.0413 (13)	0.0417 (13)	0.0000 (10)	0.0048 (10)	−0.0042 (10)
C13	0.0459 (13)	0.0357 (11)	0.0396 (12)	0.0009 (10)	0.0026 (10)	−0.0014 (9)
C14	0.0440 (13)	0.0453 (13)	0.0392 (13)	−0.0012 (10)	0.0010 (10)	−0.0044 (10)
C15	0.0561 (16)	0.0561 (16)	0.0400 (13)	0.0003 (12)	0.0014 (11)	0.0005 (11)
C16	0.096 (3)	0.075 (2)	0.0408 (16)	0.0062 (19)	0.0077 (16)	−0.0025 (15)
C17	0.105 (3)	0.087 (3)	0.0428 (18)	0.002 (2)	0.0052 (17)	0.0148 (16)
C18	0.082 (2)	0.066 (2)	0.0584 (18)	−0.0030 (17)	−0.0055 (16)	0.0194 (16)
C19	0.0693 (19)	0.0529 (16)	0.0537 (16)	−0.0031 (14)	−0.0047 (14)	0.0043 (13)
C20	0.0451 (14)	0.0531 (15)	0.0399 (13)	−0.0019 (11)	−0.0019 (11)	0.0011 (11)

Geometric parameters (Å, º) top

Cd1—N1ⁱ	2.2682 (19)	C4—C5	1.373 (5)
Cd1—N1	2.2682 (19)	C4—H4	0.9300
Cd1—O1	2.3116 (19)	C5—C6	1.397 (4)
Cd1—O1ⁱ	2.3116 (19)	C5—H5	0.9300
Cd1—O2ⁱ	2.446 (2)	C7—C8	1.472 (3)
Cd1—O2	2.446 (2)	C8—C9	1.386 (3)
O1—N5	1.269 (3)	C8—C13	1.393 (3)
O2—N5	1.260 (3)	C9—C10	1.384 (4)
O3—N5	1.525 (4)	C9—H9	0.9300
O4—H1W	0.8298	C10—C11	1.382 (4)
O4—H2W	0.8250	C10—H10	0.9300
N1—C7	1.330 (3)	C11—C12	1.397 (3)
N1—C1	1.390 (3)	C11—H11	0.9300
N2—C7	1.351 (3)	C12—C13	1.390 (3)
N2—C6	1.373 (3)	C12—C14	1.469 (3)
N2—H2n	0.8600	C13—H13	0.9300
N3—C14	1.356 (3)	C15—C20	1.394 (4)
N3—C20	1.375 (3)	C15—C16	1.404 (4)
N3—H3n	0.8600	C16—C17	1.372 (5)
N4—C14	1.321 (3)	C16—H16	0.9300
N4—C15	1.393 (4)	C17—C18	1.379 (5)
C1—C6	1.392 (3)	C17—H17	0.9300
C1—C2	1.400 (4)	C18—C19	1.371 (4)
C2—C3	1.372 (4)	C18—H18	0.9300
C2—H2	0.9300	C19—C20	1.388 (4)
C3—C4	1.390 (4)	C19—H19	0.9300
C3—H3	0.9300

N1ⁱ—Cd1—N1	101.21 (10)	N2—C6—C1	106.1 (2)
N1ⁱ—Cd1—O1	108.92 (7)	N2—C6—C5	131.9 (3)
N1—Cd1—O1	99.58 (7)	C1—C6—C5	122.0 (3)
N1ⁱ—Cd1—O1ⁱ	99.58 (7)	N1—C7—N2	111.7 (2)
N1—Cd1—O1ⁱ	108.92 (7)	N1—C7—C8	125.6 (2)
O1—Cd1—O1ⁱ	134.52 (9)	N2—C7—C8	122.7 (2)
N1ⁱ—Cd1—O2ⁱ	154.36 (7)	C9—C8—C13	119.3 (2)
N1—Cd1—O2ⁱ	91.97 (8)	C9—C8—C7	121.2 (2)
O1—Cd1—O2ⁱ	90.15 (7)	C13—C8—C7	119.5 (2)
O1ⁱ—Cd1—O2ⁱ	55.07 (6)	C8—C9—C10	120.1 (2)
N1ⁱ—Cd1—O2	91.97 (8)	C8—C9—H9	120.0
N1—Cd1—O2	154.36 (7)	C10—C9—H9	120.0
O1—Cd1—O2	55.07 (6)	C11—C10—C9	120.6 (2)
O1ⁱ—Cd1—O2	90.15 (7)	C11—C10—H10	119.7
O2ⁱ—Cd1—O2	85.00 (12)	C9—C10—H10	119.7
N5—O1—Cd1	94.53 (17)	C10—C11—C12	120.1 (2)
N5—O2—Cd1	88.56 (16)	C10—C11—H11	119.9
H1W—O4—H2W	111.9	C12—C11—H11	119.9
C7—N1—C1	105.78 (19)	C13—C12—C11	118.9 (2)
C7—N1—Cd1	129.17 (15)	C13—C12—C14	121.3 (2)
C1—N1—Cd1	120.34 (15)	C11—C12—C14	119.7 (2)
C7—N2—C6	107.7 (2)	C12—C13—C8	121.0 (2)
C7—N2—H2n	126.2	C12—C13—H13	119.5
C6—N2—H2n	126.2	C8—C13—H13	119.5
C14—N3—C20	107.8 (2)	N4—C14—N3	112.6 (2)
C14—N3—H3n	126.1	N4—C14—C12	124.4 (2)
C20—N3—H3n	126.1	N3—C14—C12	123.0 (2)
C14—N4—C15	104.6 (2)	N4—C15—C20	110.2 (2)
O2—N5—O1	121.2 (3)	N4—C15—C16	130.2 (3)
O2—N5—O3	120.1 (3)	C20—C15—C16	119.6 (3)
O1—N5—O3	118.6 (3)	C17—C16—C15	117.3 (3)
N1—C1—C6	108.7 (2)	C17—C16—H16	121.3
N1—C1—C2	131.0 (2)	C15—C16—H16	121.3
C6—C1—C2	120.2 (2)	C16—C17—C18	122.2 (3)
C3—C2—C1	117.2 (3)	C16—C17—H17	118.9
C3—C2—H2	121.4	C18—C17—H17	118.9
C1—C2—H2	121.4	C19—C18—C17	121.7 (3)
C2—C3—C4	122.3 (3)	C19—C18—H18	119.2
C2—C3—H3	118.9	C17—C18—H18	119.2
C4—C3—H3	118.9	C18—C19—C20	116.8 (3)
C3—C4—C5	121.5 (3)	C18—C19—H19	121.6
C3—C4—H4	119.3	C20—C19—H19	121.6
C5—C4—H4	119.3	N3—C20—C19	132.7 (3)
C4—C5—C6	116.8 (3)	N3—C20—C15	104.9 (2)
C4—C5—H5	121.6	C19—C20—C15	122.4 (3)
C6—C5—H5	121.6

N1ⁱ—Cd1—O1—N5	−83.37 (16)	Cd1—N1—C7—N2	−153.49 (17)
N1—Cd1—O1—N5	171.20 (16)	C1—N1—C7—C8	−178.7 (2)
O1ⁱ—Cd1—O1—N5	42.36 (14)	Cd1—N1—C7—C8	26.2 (3)
O2ⁱ—Cd1—O1—N5	79.17 (16)	C6—N2—C7—N1	−1.1 (3)
O2—Cd1—O1—N5	−4.61 (16)	C6—N2—C7—C8	179.2 (2)
N1ⁱ—Cd1—O2—N5	116.45 (17)	N1—C7—C8—C9	−153.4 (2)
N1—Cd1—O2—N5	−4.9 (3)	N2—C7—C8—C9	26.3 (4)
O1—Cd1—O2—N5	4.63 (16)	N1—C7—C8—C13	26.4 (4)
O1ⁱ—Cd1—O2—N5	−143.95 (18)	N2—C7—C8—C13	−154.0 (2)
O2ⁱ—Cd1—O2—N5	−89.06 (17)	C13—C8—C9—C10	−0.6 (4)
N1ⁱ—Cd1—N1—C7	25.06 (18)	C7—C8—C9—C10	179.2 (2)
O1—Cd1—N1—C7	136.7 (2)	C8—C9—C10—C11	0.1 (4)
O1ⁱ—Cd1—N1—C7	−79.3 (2)	C9—C10—C11—C12	−0.2 (4)
O2ⁱ—Cd1—N1—C7	−132.8 (2)	C10—C11—C12—C13	0.6 (4)
O2—Cd1—N1—C7	144.7 (2)	C10—C11—C12—C14	−179.2 (3)
N1ⁱ—Cd1—N1—C1	−126.94 (19)	C11—C12—C13—C8	−1.1 (4)
O1—Cd1—N1—C1	−15.31 (18)	C14—C12—C13—C8	178.7 (2)
O1ⁱ—Cd1—N1—C1	128.74 (17)	C9—C8—C13—C12	1.0 (4)
O2ⁱ—Cd1—N1—C1	75.18 (18)	C7—C8—C13—C12	−178.7 (2)
O2—Cd1—N1—C1	−7.3 (3)	C15—N4—C14—N3	0.2 (3)
Cd1—O2—N5—O1	−8.1 (3)	C15—N4—C14—C12	179.9 (3)
Cd1—O2—N5—O3	168.7 (3)	C20—N3—C14—N4	−0.1 (3)
Cd1—O1—N5—O2	8.6 (3)	C20—N3—C14—C12	−179.8 (2)
Cd1—O1—N5—O3	−168.2 (2)	C13—C12—C14—N4	160.1 (3)
C7—N1—C1—C6	−1.5 (3)	C11—C12—C14—N4	−20.1 (4)
Cd1—N1—C1—C6	156.26 (16)	C13—C12—C14—N3	−20.2 (4)
C7—N1—C1—C2	177.2 (3)	C11—C12—C14—N3	159.6 (3)
Cd1—N1—C1—C2	−25.0 (4)	C14—N4—C15—C20	−0.2 (3)
N1—C1—C2—C3	179.8 (3)	C14—N4—C15—C16	177.7 (3)
C6—C1—C2—C3	−1.5 (4)	N4—C15—C16—C17	−178.4 (4)
C1—C2—C3—C4	0.1 (5)	C20—C15—C16—C17	−0.7 (5)
C2—C3—C4—C5	0.9 (5)	C15—C16—C17—C18	0.0 (7)
C3—C4—C5—C6	−0.5 (5)	C16—C17—C18—C19	0.3 (7)
C7—N2—C6—C1	0.1 (3)	C17—C18—C19—C20	0.2 (5)
C7—N2—C6—C5	−179.9 (3)	C14—N3—C20—C19	−179.2 (3)
N1—C1—C6—N2	0.9 (3)	C14—N3—C20—C15	−0.1 (3)
C2—C1—C6—N2	−178.0 (2)	C18—C19—C20—N3	178.0 (3)
N1—C1—C6—C5	−179.1 (2)	C18—C19—C20—C15	−1.0 (5)
C2—C1—C6—C5	2.0 (4)	N4—C15—C20—N3	0.2 (3)
C4—C5—C6—N2	179.1 (3)	C16—C15—C20—N3	−178.0 (3)
C4—C5—C6—C1	−1.0 (4)	N4—C15—C20—C19	179.4 (3)
C1—N1—C7—N2	1.6 (3)	C16—C15—C20—C19	1.2 (5)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O4	0.86	1.88	2.720 (3)	167
N3—H3n···O1ⁱ	0.86	2.04	2.895 (3)	175
O4—H1W···O2ⁱⁱ	0.83	2.13	2.931 (3)	163
O4—H2W···N4ⁱⁱⁱ	0.83	2.02	2.837 (3)	169

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

Experimental details

Crystal data
Chemical formula	[Cd(NO₃)₂(C₂₀H₁₄N₄)₂]·2H₂O
M_r	893.16
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	293
a, b, c (Å)	14.359 (1), 16.809 (1), 16.780 (1)
V (Å³)	4049.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.49 × 0.36 × 0.25

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.735, 0.863
No. of measured, independent and observed [I > 2σ(I)] reflections	33964, 4651, 3699
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.111, 1.01
No. of reflections	4651
No. of parameters	267
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.59

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), publCIF (Westrip, 2007).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O4	0.86	1.88	2.720 (3)	167
N3—H3n···O1ⁱ	0.86	2.04	2.895 (3)	175
O4—H1W···O2ⁱⁱ	0.83	2.13	2.931 (3)	163
O4—H2W···N4ⁱⁱⁱ	0.83	2.02	2.837 (3)	169

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

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