cis-Bis­(dicyan­amido)bis(1,10-phen­an­throline)­manganese(II) and cis-bis(dicyan­amido)­bis(1,10-phen­an­thro­line)­zinc(II)

The title compounds are isomorphous, comprised of neutral monomeric [M(phen)₂(dca)₂] [(I): M = Mn, (II): M = Zn; phen is 1,10-phenanthroline, C₁₂H₈N₂; dca is dicyan­amide, C₂N₃] mol­ecules. In the mol­ecule, the divalent metal ion is in a distorted octahedral coordination environment formed by six N atoms from the phen and dca ligands. The Mn-N [2.144 (2)-2.319 (2) Å] and Zn-N [2.075 (2)-2.245 (2) Å] distances are in agreement with the difference in size of the two divalent ions.

Computing details

For both compounds, data collection: KappaCCD Software (Nonius, 1998); cell refinement: HKL SCALEPAK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

[Mn(C12H8N2)2(C2N3)2]	F(000) = 1116
Mr = 547.45	Dx = 1.441 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.7989 (2) Å	Cell parameters from 46192 reflections
b = 15.0160 (5) Å	θ = 3.5–27.9°
c = 17.7189 (5) Å	µ = 0.56 mm^−1
β = 104.5946 (16)°	T = 293 K
V = 2523.04 (12) Å^3	Block, brown
Z = 4	0.33 × 0.30 × 0.15 mm

Data collection

NONIUS KappaCCD diffractometer	6007 independent reflections
Radiation source: fine-focus sealed tube	3898 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
Detector resolution: 0.76 pixels mm^-1	θmax = 27.9°, θmin = 3.5°
CCD scans	h = −12→12
Absorption correction: empirical (using intensity measurements) (Blessing, 1995, 1997)	k = −19→19
Tmin = 0.892, Tmax = 0.922	l = −23→23
46192 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	All H-atom parameters refined
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0474P)^2 + 0.7644P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
6007 reflections	Δρmax = 0.41 e Å^−3
417 parameters	Δρmin = −0.37 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0037 (8)

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.

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.

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

	x	y	z	Uiso*/Ueq
Mn1	0.71103 (3)	0.72359 (2)	0.486394 (19)	0.04122 (13)
N1	0.86098 (19)	0.72104 (12)	0.40581 (10)	0.0453 (4)
N2	0.89337 (17)	0.63379 (11)	0.54242 (10)	0.0413 (4)
N3	0.84386 (19)	0.84409 (12)	0.54555 (10)	0.0457 (4)
N4	0.60111 (18)	0.84832 (13)	0.43119 (10)	0.0485 (5)
N5	0.5741 (2)	0.63532 (16)	0.40665 (14)	0.0661 (6)
N6	0.4986 (3)	0.5176 (2)	0.3135 (2)	0.1203 (13)
N7	0.2665 (3)	0.45710 (16)	0.25409 (14)	0.0746 (7)
N8	0.6149 (2)	0.71223 (15)	0.58252 (13)	0.0628 (6)
N9	0.5191 (3)	0.7424 (2)	0.69338 (15)	0.0959 (9)
N10	0.2761 (3)	0.7491 (2)	0.70152 (17)	0.1014 (10)
C1	0.8411 (3)	0.76041 (19)	0.33692 (15)	0.0604 (7)
C2	0.9435 (4)	0.7617 (2)	0.29475 (19)	0.0776 (9)
C3	1.0706 (4)	0.7235 (2)	0.32593 (19)	0.0744 (9)
C4	1.0970 (3)	0.68086 (16)	0.39926 (16)	0.0571 (6)
C5	1.2279 (3)	0.6394 (2)	0.4376 (2)	0.0763 (9)
C6	1.2447 (3)	0.5984 (2)	0.5055 (2)	0.0766 (9)
C7	1.1333 (2)	0.59253 (17)	0.54401 (15)	0.0556 (6)
C8	1.1427 (3)	0.54747 (19)	0.61476 (18)	0.0689 (8)
C9	1.0304 (3)	0.54472 (18)	0.64639 (17)	0.0649 (7)
C10	0.9074 (3)	0.58880 (16)	0.60893 (14)	0.0519 (6)
C11	1.0046 (2)	0.63442 (14)	0.50956 (13)	0.0413 (5)
C12	0.9862 (2)	0.68053 (14)	0.43641 (13)	0.0427 (5)
C13	0.9631 (3)	0.84234 (19)	0.60152 (15)	0.0555 (6)
C14	1.0345 (3)	0.91802 (19)	0.63543 (17)	0.0656 (7)
C15	0.9802 (3)	0.9990 (2)	0.61036 (18)	0.0692 (8)
C16	0.8547 (3)	1.00534 (16)	0.55092 (15)	0.0578 (6)
C17	0.7914 (4)	1.08754 (19)	0.5204 (2)	0.0740 (8)
C18	0.6719 (4)	1.0899 (2)	0.4638 (2)	0.0764 (9)
C19	0.6023 (3)	1.01021 (18)	0.43127 (15)	0.0593 (7)
C20	0.4762 (4)	1.0080 (2)	0.37157 (18)	0.0743 (9)
C21	0.4180 (3)	0.9297 (3)	0.34394 (18)	0.0737 (9)
C22	0.4822 (3)	0.8501 (2)	0.37460 (15)	0.0602 (7)
C23	0.6610 (3)	0.92722 (16)	0.45911 (13)	0.0483 (5)
C24	0.7899 (2)	0.92522 (15)	0.51997 (13)	0.0466 (5)
C25	0.5298 (2)	0.58158 (19)	0.36229 (16)	0.0597 (7)
C26	0.3705 (3)	0.48863 (18)	0.28341 (15)	0.0590 (6)
C27	0.5627 (2)	0.72443 (17)	0.63229 (15)	0.0560 (6)
C28	0.3860 (3)	0.74410 (19)	0.69310 (15)	0.0643 (7)
H1	0.751 (3)	0.7904 (19)	0.3172 (16)	0.076 (9)*
H2	0.920 (3)	0.792 (2)	0.248 (2)	0.098 (11)*
H3	1.136 (3)	0.7199 (19)	0.2984 (17)	0.087 (9)*
H4	1.296 (3)	0.642 (2)	0.4112 (17)	0.090 (10)*
H5	1.329 (3)	0.573 (2)	0.5300 (17)	0.086 (10)*
H6	1.230 (3)	0.519 (2)	0.6394 (17)	0.086 (9)*
H7	1.036 (3)	0.5115 (17)	0.6949 (15)	0.060 (7)*
H8	0.833 (3)	0.5885 (17)	0.6305 (15)	0.064 (8)*
H9	1.003 (3)	0.7840 (17)	0.6165 (15)	0.060 (7)*
H10	1.118 (3)	0.9119 (19)	0.6791 (17)	0.085 (9)*
H11	1.023 (3)	1.051 (2)	0.6309 (17)	0.084 (9)*
H12	0.836 (3)	1.142 (2)	0.5406 (18)	0.099 (11)*
H13	0.634 (3)	1.143 (2)	0.4435 (17)	0.087 (10)*
H14	0.439 (3)	1.065 (2)	0.3524 (17)	0.089 (10)*
H15	0.335 (3)	0.9231 (19)	0.3047 (17)	0.080 (9)*
H16	0.440 (2)	0.7933 (17)	0.3586 (14)	0.052 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mn1	0.03361 (17)	0.0468 (2)	0.0450 (2)	0.00354 (15)	0.01329 (13)	−0.00186 (15)
N1	0.0455 (9)	0.0506 (11)	0.0435 (10)	0.0006 (9)	0.0179 (8)	−0.0001 (9)
N2	0.0403 (9)	0.0399 (9)	0.0464 (10)	0.0016 (8)	0.0157 (8)	−0.0017 (8)
N3	0.0463 (10)	0.0462 (10)	0.0450 (10)	0.0016 (9)	0.0119 (8)	−0.0027 (8)
N4	0.0441 (10)	0.0598 (12)	0.0424 (11)	0.0101 (9)	0.0125 (8)	0.0020 (9)
N5	0.0442 (11)	0.0751 (15)	0.0780 (16)	−0.0076 (11)	0.0136 (11)	−0.0209 (13)
N6	0.0547 (15)	0.149 (3)	0.150 (3)	−0.0025 (17)	0.0132 (16)	−0.094 (2)
N7	0.0645 (14)	0.0774 (16)	0.0728 (16)	−0.0117 (13)	0.0004 (12)	0.0044 (13)
N8	0.0545 (11)	0.0797 (15)	0.0632 (14)	0.0098 (11)	0.0316 (11)	0.0073 (11)
N9	0.0704 (15)	0.166 (3)	0.0566 (15)	0.0325 (17)	0.0260 (13)	−0.0017 (16)
N10	0.0836 (18)	0.151 (3)	0.087 (2)	0.0352 (18)	0.0542 (16)	0.0207 (18)
C1	0.0712 (17)	0.0678 (17)	0.0462 (15)	0.0025 (14)	0.0219 (13)	0.0074 (12)
C2	0.106 (3)	0.082 (2)	0.0574 (19)	−0.0040 (19)	0.0429 (18)	0.0055 (16)
C3	0.089 (2)	0.0702 (18)	0.086 (2)	−0.0151 (17)	0.0638 (19)	−0.0118 (16)
C4	0.0553 (14)	0.0528 (14)	0.0760 (18)	−0.0091 (12)	0.0406 (13)	−0.0137 (13)
C5	0.0513 (15)	0.079 (2)	0.115 (3)	−0.0031 (15)	0.0505 (18)	−0.0166 (19)
C6	0.0377 (13)	0.084 (2)	0.110 (3)	0.0111 (14)	0.0225 (15)	−0.0106 (19)
C7	0.0395 (12)	0.0542 (14)	0.0706 (17)	0.0066 (11)	0.0089 (11)	−0.0098 (12)
C8	0.0566 (15)	0.0645 (17)	0.075 (2)	0.0187 (14)	−0.0028 (14)	0.0005 (15)
C9	0.0771 (19)	0.0583 (16)	0.0546 (17)	0.0134 (14)	0.0083 (14)	0.0074 (13)
C10	0.0581 (14)	0.0503 (13)	0.0489 (14)	0.0043 (12)	0.0166 (12)	0.0032 (11)
C11	0.0341 (10)	0.0394 (11)	0.0515 (13)	0.0001 (9)	0.0126 (9)	−0.0093 (9)
C12	0.0386 (10)	0.0429 (12)	0.0516 (13)	−0.0050 (10)	0.0210 (9)	−0.0105 (10)
C13	0.0508 (13)	0.0574 (15)	0.0547 (15)	0.0013 (12)	0.0066 (11)	−0.0083 (12)
C14	0.0601 (16)	0.0667 (18)	0.0647 (18)	−0.0089 (14)	0.0058 (14)	−0.0132 (14)
C15	0.0763 (19)	0.0630 (18)	0.0693 (19)	−0.0206 (16)	0.0204 (15)	−0.0179 (15)
C16	0.0733 (17)	0.0476 (14)	0.0596 (16)	−0.0025 (13)	0.0299 (14)	−0.0050 (12)
C17	0.107 (3)	0.0470 (15)	0.074 (2)	−0.0002 (17)	0.0341 (19)	0.0000 (15)
C18	0.120 (3)	0.0460 (15)	0.074 (2)	0.0210 (17)	0.044 (2)	0.0159 (15)
C19	0.0745 (17)	0.0597 (16)	0.0505 (15)	0.0212 (13)	0.0285 (13)	0.0116 (12)
C20	0.089 (2)	0.078 (2)	0.0625 (19)	0.0384 (19)	0.0300 (17)	0.0235 (17)
C21	0.0603 (17)	0.104 (3)	0.0540 (17)	0.0289 (18)	0.0090 (14)	0.0167 (17)
C22	0.0509 (14)	0.0784 (19)	0.0500 (15)	0.0122 (14)	0.0102 (12)	0.0039 (14)
C23	0.0586 (13)	0.0506 (13)	0.0426 (13)	0.0112 (11)	0.0253 (11)	0.0027 (10)
C24	0.0531 (12)	0.0462 (12)	0.0456 (13)	0.0037 (11)	0.0222 (10)	−0.0007 (10)
C25	0.0343 (11)	0.0750 (18)	0.0695 (17)	0.0032 (12)	0.0124 (11)	−0.0169 (15)
C26	0.0544 (14)	0.0617 (16)	0.0575 (16)	0.0017 (13)	0.0077 (13)	−0.0093 (12)
C27	0.0468 (12)	0.0686 (16)	0.0550 (15)	0.0163 (12)	0.0175 (11)	0.0104 (13)
C28	0.0688 (17)	0.0821 (19)	0.0505 (15)	0.0249 (15)	0.0306 (13)	0.0146 (13)

Geometric parameters (Å, º)

Mn1—N5	2.144 (2)	C5—H4	0.90 (3)
Mn1—N8	2.151 (2)	C6—C7	1.429 (4)
Mn1—N4	2.2569 (19)	C6—H5	0.92 (3)
Mn1—N2	2.2588 (17)	C7—C11	1.404 (3)
Mn1—N1	2.2927 (17)	C7—C8	1.407 (4)
Mn1—N3	2.3192 (19)	C8—C9	1.356 (4)
N1—C1	1.326 (3)	C8—H6	0.96 (3)
N1—C12	1.355 (3)	C9—C10	1.388 (4)
N2—C10	1.335 (3)	C9—H7	0.98 (3)
N2—C11	1.359 (2)	C10—H8	0.91 (2)
N3—C13	1.329 (3)	C11—C12	1.440 (3)
N3—C24	1.360 (3)	C13—C14	1.389 (4)
N4—C22	1.332 (3)	C13—H9	0.97 (3)
N4—C23	1.359 (3)	C14—C15	1.357 (4)
N5—C25	1.134 (3)	C14—H10	0.98 (3)
N6—C25	1.277 (4)	C15—C16	1.407 (4)
N6—C26	1.308 (4)	C15—H11	0.92 (3)
N7—C26	1.125 (3)	C16—C24	1.405 (3)
N8—C27	1.140 (3)	C16—C17	1.425 (4)
N9—C27	1.288 (3)	C17—C18	1.337 (5)
N9—C28	1.304 (4)	C17—H12	0.95 (3)
N10—C28	1.126 (3)	C18—C19	1.425 (4)
C1—C2	1.394 (4)	C18—H13	0.91 (3)
C1—H1	0.97 (3)	C19—C23	1.409 (3)
C2—C3	1.356 (5)	C19—C20	1.410 (4)
C2—H2	0.92 (3)	C20—C21	1.344 (5)
C3—C4	1.413 (4)	C20—H14	0.95 (3)
C3—H3	0.90 (3)	C21—C22	1.396 (4)
C4—C12	1.404 (3)	C21—H15	0.93 (3)
C4—C5	1.434 (4)	C22—H16	0.96 (2)
C5—C6	1.324 (5)	C23—C24	1.439 (3)
N5—Mn1—N8	98.44 (9)	C7—C8—H6	118.1 (18)
N5—Mn1—N4	94.38 (8)	C8—C9—C10	119.0 (3)
N8—Mn1—N4	98.78 (7)	C8—C9—H7	120.1 (14)
N5—Mn1—N2	102.40 (8)	C10—C9—H7	120.9 (15)
N8—Mn1—N2	93.46 (7)	N2—C10—C9	123.2 (2)
N4—Mn1—N2	157.54 (7)	N2—C10—H8	117.4 (16)
N5—Mn1—N1	88.39 (7)	C9—C10—H8	119.4 (16)
N8—Mn1—N1	165.73 (7)	N2—C11—C7	122.7 (2)
N4—Mn1—N1	93.13 (6)	N2—C11—C12	117.18 (18)
N2—Mn1—N1	72.76 (6)	C7—C11—C12	120.12 (19)
N5—Mn1—N3	165.18 (8)	N1—C12—C4	122.7 (2)
N8—Mn1—N3	90.68 (8)	N1—C12—C11	118.13 (17)
N4—Mn1—N3	72.58 (7)	C4—C12—C11	119.2 (2)
N2—Mn1—N3	88.60 (6)	N3—C13—C14	124.0 (3)
N1—Mn1—N3	85.40 (6)	N3—C13—H9	116.1 (15)
C1—N1—C12	118.5 (2)	C14—C13—H9	119.8 (15)
C1—N1—Mn1	126.67 (17)	C15—C14—C13	118.6 (3)
C12—N1—Mn1	114.61 (13)	C15—C14—H10	121.6 (18)
C10—N2—C11	117.79 (19)	C13—C14—H10	119.7 (18)
C10—N2—Mn1	125.75 (15)	C14—C15—C16	120.2 (3)
C11—N2—Mn1	116.01 (14)	C14—C15—H11	122.3 (19)
C13—N3—C24	117.5 (2)	C16—C15—H11	117.5 (19)
C13—N3—Mn1	127.57 (17)	C24—C16—C15	117.3 (2)
C24—N3—Mn1	114.93 (15)	C24—C16—C17	118.9 (3)
C22—N4—C23	118.2 (2)	C15—C16—C17	123.9 (3)
C22—N4—Mn1	125.05 (19)	C18—C17—C16	121.5 (3)
C23—N4—Mn1	116.77 (15)	C18—C17—H12	119 (2)
C25—N5—Mn1	164.47 (19)	C16—C17—H12	119 (2)
C25—N6—C26	124.6 (3)	C17—C18—C19	121.4 (3)
C27—N8—Mn1	166.2 (2)	C17—C18—H13	121 (2)
C27—N9—C28	123.0 (3)	C19—C18—H13	118 (2)
N1—C1—C2	122.8 (3)	C23—C19—C20	116.5 (3)
N1—C1—H1	116.6 (16)	C23—C19—C18	119.3 (3)
C2—C1—H1	120.7 (16)	C20—C19—C18	124.2 (3)
C3—C2—C1	119.1 (3)	C21—C20—C19	120.3 (3)
C3—C2—H2	125 (2)	C21—C20—H14	124.3 (19)
C1—C2—H2	116 (2)	C19—C20—H14	115.4 (19)
C2—C3—C4	120.2 (2)	C20—C21—C22	120.0 (3)
C2—C3—H3	121 (2)	C20—C21—H15	125.1 (19)
C4—C3—H3	119 (2)	C22—C21—H15	114.9 (19)
C12—C4—C3	116.7 (2)	N4—C22—C21	122.2 (3)
C12—C4—C5	118.8 (3)	N4—C22—H16	115.7 (15)
C3—C4—C5	124.6 (2)	C21—C22—H16	122.0 (15)
C6—C5—C4	121.7 (2)	N4—C23—C19	122.9 (2)
C6—C5—H4	123 (2)	N4—C23—C24	118.1 (2)
C4—C5—H4	115 (2)	C19—C23—C24	119.0 (2)
C5—C6—C7	121.8 (3)	N3—C24—C16	122.5 (2)
C5—C6—H5	121.3 (19)	N3—C24—C23	117.5 (2)
C7—C6—H5	116.9 (19)	C16—C24—C23	119.9 (2)
C11—C7—C8	116.9 (2)	N5—C25—N6	171.6 (3)
C11—C7—C6	118.4 (3)	N7—C26—N6	173.0 (3)
C8—C7—C6	124.7 (3)	N8—C27—N9	172.6 (3)
C9—C8—C7	120.3 (2)	N10—C28—N9	171.9 (3)
C9—C8—H6	121.5 (18)

(II)

Crystal data

[Zn(C12H8N2)2(C2N3)2]	F(000) = 1136
Mr = 557.88	Dx = 1.482 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.6800 (3) Å	Cell parameters from 35401 reflections
b = 15.0697 (7) Å	θ = 3.5–27.9°
c = 17.7166 (8) Å	µ = 1.02 mm^−1
β = 104.628 (2)°	T = 293 K
V = 2500.64 (18) Å^3	Block, colourless
Z = 4	0.20 × 0.20 × 0.18 mm

Data collection

NONIUS KappaCCD diffractometer	5913 independent reflections
Radiation source: fine-focus sealed tube	3976 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
Detector resolution: 0.76 pixels mm^-1	θmax = 27.9°, θmin = 3.5°
CCD scans	h = −12→12
Absorption correction: empirical (using intensity measurements) (Blessing, 1995, 1997)	k = −19→19
Tmin = 0.799, Tmax = 0.837	l = −23→23
35401 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	All H-atom parameters refined
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0214P)^2 + 1.5124P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
5913 reflections	Δρmax = 0.32 e Å^−3
417 parameters	Δρmin = −0.34 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0008 (4)

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.

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.

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

	x	y	z	Uiso*/Ueq
Zn1	0.71624 (3)	0.727063 (19)	0.483045 (16)	0.04251 (11)
N1	0.8608 (2)	0.72781 (14)	0.40357 (11)	0.0459 (5)
N2	0.88633 (19)	0.63846 (13)	0.53747 (11)	0.0419 (5)
N3	0.8484 (2)	0.84056 (13)	0.54461 (11)	0.0448 (5)
N4	0.6051 (2)	0.84345 (14)	0.42968 (11)	0.0467 (5)
N5	0.5856 (2)	0.63798 (18)	0.40835 (15)	0.0628 (6)
N6	0.5054 (3)	0.5193 (3)	0.3174 (2)	0.1236 (14)
N7	0.2690 (3)	0.46096 (19)	0.25924 (16)	0.0775 (8)
N8	0.6169 (2)	0.71642 (16)	0.57402 (14)	0.0595 (6)
N9	0.5249 (3)	0.7459 (2)	0.68673 (15)	0.0981 (11)
N10	0.2824 (3)	0.7482 (2)	0.69980 (17)	0.1033 (11)
C1	0.8434 (3)	0.7671 (2)	0.33503 (16)	0.0598 (7)
C2	0.9483 (4)	0.7674 (2)	0.2940 (2)	0.0752 (9)
C3	1.0743 (4)	0.7275 (2)	0.3245 (2)	0.0740 (10)
C4	1.0990 (3)	0.68420 (19)	0.39786 (17)	0.0576 (7)
C5	1.2297 (3)	0.6412 (2)	0.4364 (2)	0.0769 (10)
C6	1.2439 (3)	0.5988 (3)	0.5041 (2)	0.0760 (10)
C7	1.1285 (3)	0.59430 (19)	0.54145 (17)	0.0560 (7)
C8	1.1343 (4)	0.5484 (2)	0.6115 (2)	0.0696 (9)
C9	1.0185 (3)	0.5471 (2)	0.64140 (18)	0.0641 (8)
C10	0.8969 (3)	0.59265 (18)	0.60362 (16)	0.0528 (7)
C11	1.0004 (2)	0.63830 (15)	0.50637 (14)	0.0426 (6)
C12	0.9858 (2)	0.68508 (17)	0.43421 (14)	0.0443 (6)
C13	0.9679 (3)	0.8393 (2)	0.60136 (16)	0.0557 (7)
C14	1.0370 (3)	0.9149 (2)	0.63649 (19)	0.0662 (8)
C15	0.9817 (4)	0.9952 (3)	0.6118 (2)	0.0691 (9)
C16	0.8554 (3)	1.00152 (18)	0.55181 (17)	0.0575 (7)
C17	0.7898 (5)	1.0828 (2)	0.5218 (2)	0.0739 (9)
C18	0.6708 (5)	1.0847 (2)	0.4643 (2)	0.0752 (10)
C19	0.6023 (3)	1.0045 (2)	0.43052 (16)	0.0583 (7)
C20	0.4769 (4)	1.0018 (3)	0.3699 (2)	0.0736 (10)
C21	0.4203 (4)	0.9235 (3)	0.3415 (2)	0.0730 (10)
C22	0.4860 (3)	0.8445 (2)	0.37253 (17)	0.0576 (7)
C23	0.6624 (3)	0.92270 (18)	0.45827 (15)	0.0478 (6)
C24	0.7926 (3)	0.92107 (17)	0.52026 (15)	0.0478 (6)
C25	0.5398 (3)	0.5841 (2)	0.36520 (18)	0.0602 (8)
C26	0.3754 (3)	0.4912 (2)	0.28837 (17)	0.0614 (7)
C27	0.5659 (3)	0.7280 (2)	0.62460 (16)	0.0565 (7)
C28	0.3919 (3)	0.7446 (2)	0.68922 (16)	0.0667 (9)
H1	0.754 (3)	0.798 (2)	0.3159 (17)	0.078 (10)*
H2	0.926 (3)	0.795 (2)	0.2433 (19)	0.083 (10)*
H3	1.143 (3)	0.727 (2)	0.2996 (18)	0.083 (10)*
H4	1.309 (4)	0.643 (2)	0.411 (2)	0.117 (13)*
H5	1.328 (3)	0.568 (2)	0.5289 (18)	0.083 (10)*
H6	1.218 (3)	0.518 (2)	0.6371 (18)	0.090 (10)*
H7	1.025 (3)	0.5167 (19)	0.6905 (17)	0.069 (9)*
H8	0.817 (3)	0.5944 (17)	0.6256 (15)	0.065 (8)*
H9	1.008 (3)	0.781 (2)	0.6168 (16)	0.066 (9)*
H10	1.126 (3)	0.908 (2)	0.6755 (17)	0.079 (10)*
H11	1.017 (3)	1.045 (2)	0.6331 (17)	0.074 (10)*
H12	0.836 (3)	1.136 (2)	0.5428 (19)	0.094 (12)*
H13	0.630 (3)	1.135 (2)	0.4465 (17)	0.080 (10)*
H14	0.440 (3)	1.056 (2)	0.3526 (18)	0.082 (10)*
H15	0.348 (3)	0.915 (2)	0.3069 (18)	0.071 (10)*
H16	0.449 (3)	0.7885 (17)	0.3557 (14)	0.046 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.03497 (16)	0.04828 (18)	0.04554 (18)	0.00387 (14)	0.01247 (12)	−0.00111 (15)
N1	0.0463 (11)	0.0495 (12)	0.0435 (12)	−0.0006 (10)	0.0146 (9)	−0.0005 (11)
N2	0.0378 (10)	0.0440 (12)	0.0458 (12)	0.0012 (9)	0.0142 (9)	−0.0038 (10)
N3	0.0448 (11)	0.0456 (13)	0.0437 (12)	0.0013 (10)	0.0105 (10)	−0.0043 (10)
N4	0.0413 (11)	0.0573 (14)	0.0415 (12)	0.0110 (10)	0.0104 (10)	0.0017 (10)
N5	0.0439 (13)	0.0716 (17)	0.0715 (17)	−0.0055 (12)	0.0119 (12)	−0.0195 (14)
N6	0.0552 (17)	0.147 (3)	0.159 (3)	−0.0003 (19)	0.0094 (19)	−0.100 (3)
N7	0.0678 (17)	0.0818 (19)	0.0729 (18)	−0.0156 (15)	−0.0009 (15)	0.0022 (15)
N8	0.0502 (13)	0.0711 (17)	0.0646 (15)	0.0068 (12)	0.0286 (12)	0.0037 (13)
N9	0.0714 (18)	0.175 (3)	0.0541 (16)	0.0303 (19)	0.0274 (14)	0.0007 (18)
N10	0.085 (2)	0.156 (3)	0.085 (2)	0.040 (2)	0.0525 (18)	0.024 (2)
C1	0.0689 (19)	0.0657 (19)	0.0468 (16)	−0.0005 (17)	0.0184 (15)	0.0059 (15)
C2	0.102 (3)	0.077 (2)	0.056 (2)	0.000 (2)	0.038 (2)	0.0089 (18)
C3	0.091 (2)	0.076 (2)	0.076 (2)	−0.013 (2)	0.058 (2)	−0.0101 (19)
C4	0.0517 (16)	0.0549 (17)	0.076 (2)	−0.0083 (14)	0.0350 (15)	−0.0145 (15)
C5	0.0526 (18)	0.080 (2)	0.112 (3)	0.0005 (17)	0.047 (2)	−0.009 (2)
C6	0.0396 (17)	0.085 (2)	0.105 (3)	0.0126 (16)	0.0196 (18)	−0.006 (2)
C7	0.0435 (14)	0.0560 (17)	0.0666 (19)	0.0074 (13)	0.0105 (13)	−0.0080 (14)
C8	0.0616 (19)	0.068 (2)	0.070 (2)	0.0201 (16)	−0.0008 (17)	0.0012 (17)
C9	0.074 (2)	0.063 (2)	0.0519 (18)	0.0113 (16)	0.0091 (16)	0.0082 (16)
C10	0.0583 (17)	0.0519 (17)	0.0507 (16)	0.0049 (14)	0.0183 (14)	0.0014 (13)
C11	0.0398 (12)	0.0403 (14)	0.0487 (14)	0.0004 (11)	0.0131 (11)	−0.0084 (11)
C12	0.0414 (13)	0.0454 (14)	0.0505 (15)	−0.0037 (11)	0.0197 (12)	−0.0090 (12)
C13	0.0564 (17)	0.0565 (19)	0.0513 (17)	0.0014 (15)	0.0082 (14)	−0.0062 (15)
C14	0.0594 (19)	0.070 (2)	0.063 (2)	−0.0085 (17)	0.0032 (16)	−0.0145 (17)
C15	0.078 (2)	0.061 (2)	0.068 (2)	−0.0193 (19)	0.0182 (18)	−0.0187 (18)
C16	0.0729 (19)	0.0462 (16)	0.0587 (18)	−0.0023 (15)	0.0265 (16)	−0.0052 (14)
C17	0.106 (3)	0.0484 (19)	0.071 (2)	−0.003 (2)	0.029 (2)	−0.0023 (19)
C18	0.115 (3)	0.046 (2)	0.073 (2)	0.019 (2)	0.040 (2)	0.0117 (18)
C19	0.0690 (18)	0.0629 (19)	0.0481 (17)	0.0218 (16)	0.0242 (15)	0.0135 (14)
C20	0.091 (3)	0.075 (3)	0.061 (2)	0.033 (2)	0.0297 (19)	0.022 (2)
C21	0.063 (2)	0.099 (3)	0.054 (2)	0.026 (2)	0.0083 (17)	0.015 (2)
C22	0.0519 (17)	0.068 (2)	0.0510 (17)	0.0108 (16)	0.0090 (14)	0.0019 (16)
C23	0.0556 (15)	0.0499 (16)	0.0438 (15)	0.0112 (13)	0.0237 (13)	0.0028 (12)
C24	0.0557 (15)	0.0479 (15)	0.0450 (14)	0.0023 (14)	0.0225 (13)	−0.0037 (13)
C25	0.0353 (14)	0.075 (2)	0.069 (2)	0.0074 (14)	0.0105 (14)	−0.0151 (18)
C26	0.0573 (18)	0.065 (2)	0.0569 (18)	0.0009 (16)	0.0053 (15)	−0.0080 (15)
C27	0.0448 (14)	0.0692 (18)	0.0571 (17)	0.0166 (14)	0.0158 (13)	0.0125 (15)
C28	0.070 (2)	0.090 (2)	0.0489 (16)	0.0273 (17)	0.0306 (15)	0.0168 (15)

Geometric parameters (Å, º)

Zn1—N5	2.075 (3)	C5—H4	0.98 (4)
Zn1—N8	2.081 (2)	C6—C7	1.437 (4)
Zn1—N4	2.148 (2)	C6—H5	0.94 (3)
Zn1—N2	2.1498 (19)	C7—C11	1.405 (3)
Zn1—N1	2.2217 (19)	C7—C8	1.410 (4)
Zn1—N3	2.246 (2)	C8—C9	1.355 (4)
N1—C1	1.323 (3)	C8—H6	0.94 (3)
N1—C12	1.357 (3)	C9—C10	1.381 (4)
N2—C10	1.342 (3)	C9—H7	0.97 (3)
N2—C11	1.353 (3)	C10—H8	0.95 (3)
N3—C13	1.328 (3)	C11—C12	1.435 (3)
N3—C24	1.353 (3)	C13—C14	1.386 (4)
N4—C22	1.329 (3)	C13—H9	0.97 (3)
N4—C23	1.360 (3)	C14—C15	1.351 (5)
N5—C25	1.127 (3)	C14—H10	0.97 (3)
N6—C25	1.280 (4)	C15—C16	1.406 (4)
N6—C26	1.304 (4)	C15—H11	0.86 (3)
N7—C26	1.126 (3)	C16—C24	1.407 (4)
N8—C27	1.140 (3)	C16—C17	1.420 (4)
N9—C27	1.289 (4)	C17—C18	1.332 (5)
N9—C28	1.300 (4)	C17—H12	0.94 (3)
N10—C28	1.123 (4)	C18—C19	1.435 (5)
C1—C2	1.390 (4)	C18—H13	0.88 (3)
C1—H1	0.97 (3)	C19—C23	1.399 (4)
C2—C3	1.345 (5)	C19—C20	1.404 (4)
C2—H2	0.96 (3)	C20—C21	1.344 (5)
C3—C4	1.420 (4)	C20—H14	0.91 (3)
C3—H3	0.89 (3)	C21—C22	1.395 (5)
C4—C12	1.404 (3)	C21—H15	0.82 (3)
C4—C5	1.432 (4)	C22—H16	0.93 (2)
C5—C6	1.335 (5)	C23—C24	1.448 (4)
N5—Zn1—N8	96.76 (9)	C7—C8—H6	120 (2)
N5—Zn1—N4	95.21 (9)	C8—C9—C10	119.4 (3)
N8—Zn1—N4	97.23 (8)	C8—C9—H7	119.1 (16)
N5—Zn1—N2	99.12 (9)	C10—C9—H7	121.4 (16)
N8—Zn1—N2	93.22 (8)	N2—C10—C9	123.1 (3)
N4—Zn1—N2	161.14 (8)	N2—C10—H8	116.9 (16)
N5—Zn1—N1	88.79 (8)	C9—C10—H8	119.9 (16)
N8—Zn1—N1	168.35 (8)	N2—C11—C7	122.7 (2)
N4—Zn1—N1	92.44 (7)	N2—C11—C12	117.1 (2)
N2—Zn1—N1	75.75 (7)	C7—C11—C12	120.2 (2)
N5—Zn1—N3	169.30 (9)	N1—C12—C4	122.8 (2)
N8—Zn1—N3	90.02 (8)	N1—C12—C11	117.8 (2)
N4—Zn1—N3	75.67 (8)	C4—C12—C11	119.4 (2)
N2—Zn1—N3	88.71 (8)	N3—C13—C14	123.9 (3)
N1—Zn1—N3	86.07 (7)	N3—C13—H9	116.0 (17)
C1—N1—C12	118.3 (2)	C14—C13—H9	120.0 (17)
C1—N1—Zn1	128.98 (19)	C15—C14—C13	118.9 (3)
C12—N1—Zn1	112.63 (15)	C15—C14—H10	122.5 (19)
C10—N2—C11	117.7 (2)	C13—C14—H10	118.4 (19)
C10—N2—Zn1	126.31 (17)	C14—C15—C16	120.2 (3)
C11—N2—Zn1	115.46 (16)	C14—C15—H11	123 (2)
C13—N3—C24	117.1 (2)	C16—C15—H11	116 (2)
C13—N3—Zn1	129.61 (19)	C15—C16—C24	116.6 (3)
C24—N3—Zn1	113.29 (17)	C15—C16—C17	124.2 (3)
C22—N4—C23	117.9 (2)	C24—C16—C17	119.2 (3)
C22—N4—Zn1	125.9 (2)	C18—C17—C16	121.6 (3)
C23—N4—Zn1	116.19 (16)	C18—C17—H12	121 (2)
C25—N5—Zn1	166.2 (2)	C16—C17—H12	118 (2)
C25—N6—C26	124.9 (3)	C17—C18—C19	121.3 (3)
C27—N8—Zn1	166.7 (2)	C17—C18—H13	121 (2)
C27—N9—C28	123.2 (3)	C19—C18—H13	118 (2)
N1—C1—C2	122.7 (3)	C23—C19—C20	116.4 (3)
N1—C1—H1	115.8 (18)	C23—C19—C18	119.3 (3)
C2—C1—H1	121.5 (18)	C20—C19—C18	124.3 (3)
C3—C2—C1	119.9 (3)	C21—C20—C19	120.3 (3)
C3—C2—H2	122.4 (18)	C21—C20—H14	125 (2)
C1—C2—H2	117.7 (19)	C19—C20—H14	115 (2)
C2—C3—C4	119.9 (3)	C20—C21—C22	119.9 (4)
C2—C3—H3	122 (2)	C20—C21—H15	128 (2)
C4—C3—H3	118 (2)	C22—C21—H15	112 (2)
C12—C4—C3	116.4 (3)	N4—C22—C21	122.1 (3)
C12—C4—C5	118.9 (3)	N4—C22—H16	114.7 (16)
C3—C4—C5	124.7 (3)	C21—C22—H16	123.1 (16)
C6—C5—C4	121.6 (3)	N4—C23—C19	123.3 (3)
C6—C5—H4	120 (2)	N4—C23—C24	117.6 (2)
C4—C5—H4	118 (2)	C19—C23—C24	119.1 (3)
C5—C6—C7	121.4 (3)	N3—C24—C16	123.2 (3)
C5—C6—H5	122.2 (19)	N3—C24—C23	117.2 (2)
C7—C6—H5	116.4 (19)	C16—C24—C23	119.5 (2)
C11—C7—C8	117.1 (3)	N5—C25—N6	172.2 (3)
C11—C7—C6	118.4 (3)	N7—C26—N6	173.1 (3)
C8—C7—C6	124.4 (3)	N8—C27—N9	172.1 (3)
C9—C8—C7	119.9 (3)	N10—C28—N9	171.8 (4)
C9—C8—H6	120 (2)