Crystal structure and Hirshfeld surface analysis of di­iodido­{N′-[(E)-(phen­yl)(pyridin-2-yl-κN)methylidene]pyridine-2-carbohydrazide-κ²N′,O}cadmium(II)

The title compound contains two mol­ecules in the asymmetric unit: both feature a distorted square-pyramidal CdN₂OI₂ coordination polyhedron and an intra­molecular N—H...N hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.027
• wR factor = 0.064
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.27 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         11 Report
PLAT973_ALERT_2_C Check Calcd Positive Resid. Density on       Cd1       1.04 eA-3
PLAT975_ALERT_2_C Check Calcd Resid. Dens.  1.09A   From O1              0.49 eA-3
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       5.71 Why ?
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I3       --Cd2      .        6.6 s.u.
PLAT794_ALERT_5_G Tentative Bond Valency for Cd1       (II)      .       2.24 Info
PLAT794_ALERT_5_G Tentative Bond Valency for Cd2       (II)      .       2.26 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        873 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          9 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   3 ALERT type 5 Informative message, check

---

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2015).

Diiodido{N'-[(E)-(phenyl)(pyridin-2-yl-κN)methylidene]pyridine-2-carbohydrazide-κ²N',O}cadmium(II)

Crystal data

[CdI2(C18H14N4O)]	F(000) = 2496
Mr = 668.53	Dx = 2.200 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.9158 (15) Å	Cell parameters from 9930 reflections
b = 11.7252 (9) Å	θ = 2.2–27.8°
c = 17.8349 (14) Å	µ = 4.16 mm^−1
β = 104.207 (1)°	T = 100 K
V = 4037.4 (5) Å^3	Hexagonal prism, yellow
Z = 8	0.34 × 0.33 × 0.17 mm

Data collection

Bruker SMART APEX diffractometer	7948 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 28.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −26→25
Tmin = 0.600, Tmax = 0.746	k = −15→12
24216 measured reflections	l = −20→22
9018 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.027	H-atom parameters constrained
wR(F^2) = 0.064	w = 1/[σ^2(Fo^2) + (0.0306P)^2 + 5.7109P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
9018 reflections	Δρmax = 1.26 e Å^−3
469 parameters	Δρmin = −0.56 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
C1	−0.15988 (18)	0.7689 (3)	0.5679 (2)	0.0265 (8)
H1	−0.200797	0.761245	0.527529	0.032*
C2	−0.1651 (2)	0.8147 (3)	0.6379 (2)	0.0296 (8)
H2	−0.208603	0.839406	0.644720	0.036*
C3	−0.1066 (2)	0.8238 (3)	0.6971 (2)	0.0295 (8)
H3A	−0.108958	0.855873	0.745277	0.035*
C4	−0.04377 (18)	0.7855 (3)	0.6858 (2)	0.0245 (7)
H4	−0.002709	0.789869	0.726250	0.029*
C5	−0.04221 (17)	0.7409 (3)	0.6145 (2)	0.0218 (7)
C6	0.02285 (17)	0.6967 (3)	0.59802 (19)	0.0205 (7)
C7	0.08845 (17)	0.6963 (3)	0.65920 (19)	0.0210 (7)
C8	0.09709 (19)	0.6246 (3)	0.7225 (2)	0.0292 (8)
H8	0.060605	0.575262	0.727562	0.035*
C9	0.1594 (2)	0.6251 (4)	0.7788 (2)	0.0352 (9)
H9	0.165419	0.575842	0.822230	0.042*
C10	0.2129 (2)	0.6974 (4)	0.7716 (2)	0.0342 (9)
H10	0.255585	0.697081	0.809828	0.041*
C11	0.2035 (2)	0.7697 (4)	0.7086 (2)	0.0339 (9)
H11	0.239690	0.820040	0.703963	0.041*
C12	0.1420 (2)	0.7691 (3)	0.6523 (2)	0.0306 (8)
H12	0.136162	0.818266	0.608864	0.037*
C13	0.06053 (17)	0.5883 (3)	0.4289 (2)	0.0214 (7)
C14	0.12412 (17)	0.5528 (3)	0.4049 (2)	0.0216 (7)
C15	0.11899 (18)	0.5094 (3)	0.3316 (2)	0.0242 (7)
H15	0.075311	0.501950	0.295562	0.029*
C16	0.17994 (19)	0.4772 (3)	0.3122 (2)	0.0283 (8)
H16	0.178904	0.447717	0.262261	0.034*
C17	0.24142 (18)	0.4888 (3)	0.3667 (2)	0.0304 (8)
H17	0.283676	0.466404	0.355316	0.036*
C18	0.24135 (18)	0.5336 (3)	0.4386 (2)	0.0279 (8)
H18	0.284391	0.541529	0.475719	0.033*
Cd1	−0.08166 (2)	0.70487 (2)	0.42925 (2)	0.02325 (6)
I1	−0.02803 (2)	0.89997 (2)	0.38096 (2)	0.02834 (6)
I2	−0.20450 (2)	0.60932 (2)	0.36168 (2)	0.03106 (7)
N1	−0.09966 (14)	0.7350 (3)	0.55485 (17)	0.0232 (6)
N2	0.01685 (14)	0.6622 (2)	0.52758 (16)	0.0215 (6)
N3	0.07222 (14)	0.6208 (3)	0.50403 (16)	0.0226 (6)
H3	0.113503	0.615314	0.535951	0.027*
N4	0.18386 (15)	0.5661 (3)	0.45830 (18)	0.0253 (6)
O1	0.00248 (12)	0.5878 (2)	0.38410 (14)	0.0256 (5)
C19	0.47181 (19)	0.5871 (3)	0.5866 (2)	0.0270 (8)
H19	0.511452	0.549614	0.577806	0.032*
C20	0.4403 (2)	0.5409 (3)	0.6405 (2)	0.0314 (8)
H20	0.457550	0.472829	0.667323	0.038*
C21	0.3830 (2)	0.5955 (3)	0.6547 (2)	0.0303 (8)
H21	0.359945	0.565392	0.691081	0.036*
C22	0.36007 (19)	0.6954 (3)	0.6145 (2)	0.0261 (7)
H22	0.321326	0.735372	0.623582	0.031*
C23	0.39437 (17)	0.7359 (3)	0.5611 (2)	0.0224 (7)
C24	0.37348 (17)	0.8435 (3)	0.5184 (2)	0.0225 (7)
C25	0.30874 (18)	0.9009 (3)	0.5247 (2)	0.0255 (8)
C26	0.3113 (2)	0.9956 (4)	0.5723 (3)	0.0385 (10)
H26	0.354632	1.025469	0.599897	0.046*
C27	0.2505 (3)	1.0457 (4)	0.5790 (3)	0.0543 (13)
H27	0.251823	1.110396	0.611406	0.065*
C28	0.1876 (3)	1.0018 (4)	0.5387 (3)	0.0526 (14)
H28	0.145841	1.036347	0.544022	0.063*
C29	0.1845 (2)	0.9088 (4)	0.4909 (3)	0.0438 (11)
H29	0.140978	0.879841	0.462879	0.053*
C30	0.2457 (2)	0.8577 (4)	0.4840 (3)	0.0350 (9)
H30	0.244173	0.793135	0.451413	0.042*
C31	0.43945 (18)	1.0017 (3)	0.3850 (2)	0.0245 (7)
C32	0.41803 (18)	1.1068 (3)	0.3382 (2)	0.0238 (7)
C33	0.4640 (2)	1.1575 (3)	0.3007 (2)	0.0269 (8)
H33	0.508151	1.124917	0.303051	0.032*
C34	0.4431 (2)	1.2568 (3)	0.2598 (2)	0.0307 (8)
H34	0.472542	1.294272	0.233131	0.037*
C35	0.3784 (2)	1.3003 (3)	0.2587 (2)	0.0304 (8)
H35	0.363169	1.369376	0.232195	0.036*
C36	0.3361 (2)	1.2419 (3)	0.2967 (2)	0.0294 (8)
H36	0.291160	1.271413	0.293948	0.035*
Cd2	0.49190 (2)	0.75304 (2)	0.44240 (2)	0.02348 (6)
I3	0.39729 (2)	0.65574 (2)	0.32031 (2)	0.02644 (6)
I4	0.62809 (2)	0.71202 (2)	0.47863 (2)	0.03079 (7)
N5	0.44979 (15)	0.6813 (3)	0.54638 (17)	0.0241 (6)
N6	0.41289 (15)	0.8790 (2)	0.47642 (17)	0.0233 (6)
N7	0.39722 (15)	0.9746 (2)	0.43223 (17)	0.0246 (6)
H7	0.361299	1.017289	0.434038	0.030*
N8	0.35512 (15)	1.1468 (3)	0.33692 (18)	0.0266 (6)
O2	0.49091 (13)	0.9444 (2)	0.38286 (15)	0.0294 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0237 (17)	0.030 (2)	0.0272 (19)	0.0041 (15)	0.0095 (15)	0.0072 (15)
C2	0.0316 (19)	0.033 (2)	0.029 (2)	0.0070 (16)	0.0171 (16)	0.0084 (16)
C3	0.041 (2)	0.030 (2)	0.0241 (19)	0.0062 (16)	0.0192 (17)	0.0042 (15)
C4	0.0274 (17)	0.0256 (19)	0.0219 (18)	0.0009 (14)	0.0085 (14)	0.0011 (14)
C5	0.0210 (16)	0.0223 (17)	0.0244 (18)	−0.0003 (13)	0.0101 (14)	0.0030 (14)
C6	0.0209 (16)	0.0217 (17)	0.0199 (17)	−0.0009 (13)	0.0066 (13)	−0.0004 (13)
C7	0.0193 (15)	0.0247 (18)	0.0190 (16)	−0.0002 (13)	0.0049 (13)	−0.0033 (13)
C8	0.0287 (18)	0.029 (2)	0.029 (2)	−0.0017 (15)	0.0043 (15)	0.0055 (15)
C9	0.035 (2)	0.036 (2)	0.030 (2)	−0.0039 (17)	−0.0013 (17)	0.0058 (17)
C10	0.0255 (18)	0.042 (2)	0.032 (2)	−0.0019 (17)	0.0016 (16)	−0.0077 (18)
C11	0.0280 (19)	0.042 (2)	0.035 (2)	−0.0105 (17)	0.0130 (17)	−0.0033 (18)
C12	0.034 (2)	0.036 (2)	0.0242 (19)	−0.0050 (17)	0.0111 (16)	0.0030 (16)
C13	0.0248 (17)	0.0197 (17)	0.0212 (17)	0.0010 (13)	0.0084 (14)	0.0022 (13)
C14	0.0220 (16)	0.0196 (17)	0.0241 (18)	0.0013 (13)	0.0075 (14)	0.0027 (13)
C15	0.0246 (17)	0.0250 (18)	0.0234 (18)	−0.0014 (14)	0.0069 (14)	0.0001 (14)
C16	0.0298 (18)	0.028 (2)	0.031 (2)	0.0020 (15)	0.0164 (16)	0.0002 (16)
C17	0.0232 (17)	0.028 (2)	0.043 (2)	0.0032 (15)	0.0142 (16)	−0.0020 (17)
C18	0.0197 (16)	0.0265 (19)	0.037 (2)	−0.0008 (14)	0.0063 (15)	−0.0052 (16)
Cd1	0.01973 (12)	0.03217 (15)	0.01853 (13)	0.00340 (10)	0.00597 (10)	0.00226 (10)
I1	0.02828 (12)	0.03337 (14)	0.02603 (13)	0.00073 (10)	0.01178 (10)	0.00283 (10)
I2	0.02091 (11)	0.04454 (16)	0.02837 (13)	−0.00209 (10)	0.00728 (9)	−0.00054 (11)
N1	0.0219 (14)	0.0293 (16)	0.0201 (15)	0.0026 (12)	0.0087 (12)	0.0045 (12)
N2	0.0196 (13)	0.0252 (15)	0.0218 (15)	0.0054 (11)	0.0087 (11)	0.0014 (12)
N3	0.0195 (13)	0.0299 (16)	0.0186 (14)	0.0059 (12)	0.0052 (11)	−0.0005 (12)
N4	0.0235 (14)	0.0240 (15)	0.0282 (16)	0.0021 (12)	0.0056 (12)	−0.0024 (12)
O1	0.0227 (12)	0.0337 (14)	0.0206 (12)	0.0040 (10)	0.0057 (10)	−0.0023 (10)
C19	0.0298 (18)	0.0232 (18)	0.0265 (19)	0.0055 (15)	0.0038 (15)	0.0003 (14)
C20	0.044 (2)	0.029 (2)	0.0211 (18)	0.0063 (17)	0.0077 (16)	0.0018 (15)
C21	0.041 (2)	0.030 (2)	0.0222 (19)	0.0011 (16)	0.0106 (16)	0.0025 (15)
C22	0.0300 (18)	0.0263 (19)	0.0239 (18)	0.0039 (15)	0.0100 (15)	0.0004 (15)
C23	0.0252 (17)	0.0218 (17)	0.0198 (17)	0.0017 (14)	0.0046 (14)	−0.0012 (13)
C24	0.0243 (16)	0.0219 (17)	0.0219 (17)	0.0028 (14)	0.0067 (14)	−0.0026 (14)
C25	0.0300 (18)	0.0250 (19)	0.0268 (19)	0.0060 (14)	0.0172 (15)	0.0085 (14)
C26	0.047 (2)	0.031 (2)	0.042 (2)	0.0089 (18)	0.019 (2)	−0.0008 (18)
C27	0.073 (3)	0.042 (3)	0.061 (3)	0.023 (3)	0.042 (3)	0.004 (2)
C28	0.052 (3)	0.046 (3)	0.075 (4)	0.025 (2)	0.045 (3)	0.033 (3)
C29	0.027 (2)	0.048 (3)	0.059 (3)	0.0041 (18)	0.017 (2)	0.027 (2)
C30	0.0312 (19)	0.034 (2)	0.044 (2)	0.0024 (17)	0.0165 (18)	0.0093 (18)
C31	0.0306 (18)	0.0219 (18)	0.0230 (18)	−0.0023 (14)	0.0102 (15)	−0.0020 (14)
C32	0.0310 (18)	0.0215 (18)	0.0196 (17)	−0.0063 (14)	0.0076 (14)	−0.0062 (13)
C33	0.0352 (19)	0.0255 (19)	0.0213 (18)	−0.0065 (15)	0.0098 (15)	−0.0066 (14)
C34	0.043 (2)	0.027 (2)	0.0218 (19)	−0.0086 (17)	0.0082 (16)	−0.0013 (15)
C35	0.042 (2)	0.0246 (19)	0.0251 (19)	0.0006 (16)	0.0099 (17)	0.0026 (15)
C36	0.0334 (19)	0.0263 (19)	0.029 (2)	0.0031 (15)	0.0077 (16)	0.0028 (15)
Cd2	0.02161 (12)	0.02587 (14)	0.02434 (13)	0.00368 (10)	0.00830 (10)	−0.00026 (10)
I3	0.01929 (11)	0.03300 (13)	0.02632 (12)	0.00173 (9)	0.00425 (9)	0.00129 (10)
I4	0.02047 (11)	0.03842 (15)	0.03207 (14)	0.00249 (10)	0.00375 (10)	−0.00371 (10)
N5	0.0261 (15)	0.0262 (16)	0.0203 (15)	0.0034 (12)	0.0061 (12)	0.0000 (12)
N6	0.0266 (15)	0.0211 (15)	0.0233 (15)	0.0016 (12)	0.0086 (12)	0.0016 (12)
N7	0.0315 (15)	0.0195 (15)	0.0266 (16)	0.0056 (12)	0.0143 (13)	0.0052 (12)
N8	0.0280 (15)	0.0262 (16)	0.0277 (16)	−0.0005 (13)	0.0107 (13)	−0.0019 (13)
O2	0.0292 (13)	0.0266 (14)	0.0361 (15)	0.0038 (11)	0.0152 (11)	0.0024 (11)

Geometric parameters (Å, º)

C1—N1	1.337 (4)	C19—N5	1.331 (5)
C1—C2	1.385 (5)	C19—C20	1.382 (5)
C1—H1	0.9500	C19—H19	0.9500
C2—C3	1.371 (5)	C20—C21	1.384 (5)
C2—H2	0.9500	C20—H20	0.9500
C3—C4	1.389 (5)	C21—C22	1.391 (5)
C3—H3A	0.9500	C21—H21	0.9500
C4—C5	1.381 (5)	C22—C23	1.385 (5)
C4—H4	0.9500	C22—H22	0.9500
C5—N1	1.360 (4)	C23—N5	1.356 (4)
C5—C6	1.491 (5)	C23—C24	1.480 (5)
C6—N2	1.297 (4)	C24—N6	1.280 (5)
C6—C7	1.482 (4)	C24—C25	1.483 (5)
C7—C8	1.385 (5)	C25—C30	1.383 (5)
C7—C12	1.395 (5)	C25—C26	1.391 (6)
C8—C9	1.391 (5)	C26—C27	1.377 (6)
C8—H8	0.9500	C26—H26	0.9500
C9—C10	1.392 (6)	C27—C28	1.382 (8)
C9—H9	0.9500	C27—H27	0.9500
C10—C11	1.385 (6)	C28—C29	1.376 (7)
C10—H10	0.9500	C28—H28	0.9500
C11—C12	1.380 (5)	C29—C30	1.391 (6)
C11—H11	0.9500	C29—H29	0.9500
C12—H12	0.9500	C30—H30	0.9500
C13—O1	1.233 (4)	C31—O2	1.234 (4)
C13—N3	1.357 (4)	C31—N7	1.366 (4)
C13—C14	1.492 (5)	C31—C32	1.491 (5)
C14—N4	1.338 (4)	C32—N8	1.332 (5)
C14—C15	1.384 (5)	C32—C33	1.393 (5)
C15—C16	1.394 (5)	C33—C34	1.382 (5)
C15—H15	0.9500	C33—H33	0.9500
C16—C17	1.371 (5)	C34—C35	1.380 (6)
C16—H16	0.9500	C34—H34	0.9500
C17—C18	1.387 (5)	C35—C36	1.385 (5)
C17—H17	0.9500	C35—H35	0.9500
C18—N4	1.333 (4)	C36—N8	1.330 (5)
C18—H18	0.9500	C36—H36	0.9500
Cd1—N2	2.342 (3)	Cd2—N6	2.344 (3)
Cd1—N1	2.380 (3)	Cd2—N5	2.369 (3)
Cd1—O1	2.450 (2)	Cd2—O2	2.481 (3)
Cd1—I2	2.6917 (4)	Cd2—I4	2.6732 (4)
Cd1—I1	2.7509 (4)	Cd2—I3	2.7530 (4)
N2—N3	1.362 (4)	N6—N7	1.362 (4)
N3—H3	0.8800	N7—H7	0.8800
N1—C1—C2	122.7 (3)	N5—C19—C20	123.7 (3)
N1—C1—H1	118.6	N5—C19—H19	118.1
C2—C1—H1	118.6	C20—C19—H19	118.1
C3—C2—C1	119.1 (3)	C19—C20—C21	118.8 (4)
C3—C2—H2	120.4	C19—C20—H20	120.6
C1—C2—H2	120.4	C21—C20—H20	120.6
C2—C3—C4	119.2 (3)	C20—C21—C22	118.5 (4)
C2—C3—H3A	120.4	C20—C21—H21	120.8
C4—C3—H3A	120.4	C22—C21—H21	120.8
C5—C4—C3	118.7 (3)	C23—C22—C21	119.2 (3)
C5—C4—H4	120.7	C23—C22—H22	120.4
C3—C4—H4	120.7	C21—C22—H22	120.4
N1—C5—C4	122.3 (3)	N5—C23—C22	122.3 (3)
N1—C5—C6	115.6 (3)	N5—C23—C24	116.2 (3)
C4—C5—C6	122.0 (3)	C22—C23—C24	121.5 (3)
N2—C6—C7	124.6 (3)	N6—C24—C23	116.3 (3)
N2—C6—C5	115.0 (3)	N6—C24—C25	124.4 (3)
C7—C6—C5	120.5 (3)	C23—C24—C25	119.2 (3)
C8—C7—C12	119.9 (3)	C30—C25—C26	120.3 (4)
C8—C7—C6	120.8 (3)	C30—C25—C24	119.2 (3)
C12—C7—C6	119.3 (3)	C26—C25—C24	120.4 (4)
C7—C8—C9	119.7 (4)	C27—C26—C25	119.5 (4)
C7—C8—H8	120.1	C27—C26—H26	120.2
C9—C8—H8	120.1	C25—C26—H26	120.2
C8—C9—C10	120.3 (4)	C26—C27—C28	120.0 (5)
C8—C9—H9	119.9	C26—C27—H27	120.0
C10—C9—H9	119.9	C28—C27—H27	120.0
C11—C10—C9	119.6 (4)	C29—C28—C27	121.0 (4)
C11—C10—H10	120.2	C29—C28—H28	119.5
C9—C10—H10	120.2	C27—C28—H28	119.5
C12—C11—C10	120.4 (4)	C28—C29—C30	119.3 (4)
C12—C11—H11	119.8	C28—C29—H29	120.4
C10—C11—H11	119.8	C30—C29—H29	120.4
C11—C12—C7	120.1 (4)	C25—C30—C29	119.9 (4)
C11—C12—H12	120.0	C25—C30—H30	120.1
C7—C12—H12	120.0	C29—C30—H30	120.1
O1—C13—N3	123.2 (3)	O2—C31—N7	122.3 (3)
O1—C13—C14	122.7 (3)	O2—C31—C32	124.0 (3)
N3—C13—C14	114.1 (3)	N7—C31—C32	113.7 (3)
N4—C14—C15	124.2 (3)	N8—C32—C33	124.6 (3)
N4—C14—C13	115.7 (3)	N8—C32—C31	116.0 (3)
C15—C14—C13	120.2 (3)	C33—C32—C31	119.3 (3)
C14—C15—C16	117.9 (3)	C34—C33—C32	117.6 (4)
C14—C15—H15	121.1	C34—C33—H33	121.2
C16—C15—H15	121.1	C32—C33—H33	121.2
C17—C16—C15	118.5 (3)	C35—C34—C33	118.6 (4)
C17—C16—H16	120.7	C35—C34—H34	120.7
C15—C16—H16	120.7	C33—C34—H34	120.7
C16—C17—C18	119.4 (3)	C34—C35—C36	119.2 (4)
C16—C17—H17	120.3	C34—C35—H35	120.4
C18—C17—H17	120.3	C36—C35—H35	120.4
N4—C18—C17	123.2 (3)	N8—C36—C35	123.5 (4)
N4—C18—H18	118.4	N8—C36—H36	118.3
C17—C18—H18	118.4	C35—C36—H36	118.3
N2—Cd1—N1	67.60 (9)	N6—Cd2—N5	68.41 (10)
N2—Cd1—O1	67.15 (9)	N6—Cd2—O2	66.77 (9)
N1—Cd1—O1	131.72 (9)	N5—Cd2—O2	133.56 (9)
N2—Cd1—I2	138.47 (7)	N6—Cd2—I4	139.16 (7)
N1—Cd1—I2	98.79 (7)	N5—Cd2—I4	106.26 (7)
O1—Cd1—I2	103.85 (6)	O2—Cd2—I4	99.62 (6)
N2—Cd1—I1	95.38 (7)	N6—Cd2—I3	95.35 (7)
N1—Cd1—I1	109.34 (7)	N5—Cd2—I3	99.61 (7)
O1—Cd1—I1	90.77 (6)	O2—Cd2—I3	95.99 (6)
I2—Cd1—I1	125.873 (12)	I4—Cd2—I3	124.998 (12)
C1—N1—C5	117.8 (3)	C19—N5—C23	117.6 (3)
C1—N1—Cd1	123.8 (2)	C19—N5—Cd2	125.7 (2)
C5—N1—Cd1	116.9 (2)	C23—N5—Cd2	116.4 (2)
C6—N2—N3	121.4 (3)	C24—N6—N7	121.4 (3)
C6—N2—Cd1	121.3 (2)	C24—N6—Cd2	119.5 (2)
N3—N2—Cd1	116.0 (2)	N7—N6—Cd2	116.2 (2)
C13—N3—N2	116.7 (3)	N6—N7—C31	117.4 (3)
C13—N3—H3	121.7	N6—N7—H7	121.3
N2—N3—H3	121.7	C31—N7—H7	121.3
C18—N4—C14	116.8 (3)	C36—N8—C32	116.5 (3)
C13—O1—Cd1	113.1 (2)	C31—O2—Cd2	113.5 (2)
N1—C1—C2—C3	−1.4 (6)	N5—C19—C20—C21	−0.9 (6)
C1—C2—C3—C4	−0.9 (6)	C19—C20—C21—C22	−0.6 (6)
C2—C3—C4—C5	1.0 (5)	C20—C21—C22—C23	0.9 (6)
C3—C4—C5—N1	1.1 (5)	C21—C22—C23—N5	0.1 (5)
C3—C4—C5—C6	−179.2 (3)	C21—C22—C23—C24	−178.2 (3)
N1—C5—C6—N2	2.6 (4)	N5—C23—C24—N6	−5.3 (5)
C4—C5—C6—N2	−177.1 (3)	C22—C23—C24—N6	173.1 (3)
N1—C5—C6—C7	−178.6 (3)	N5—C23—C24—C25	173.1 (3)
C4—C5—C6—C7	1.7 (5)	C22—C23—C24—C25	−8.5 (5)
N2—C6—C7—C8	−112.8 (4)	N6—C24—C25—C30	101.6 (4)
C5—C6—C7—C8	68.6 (5)	C23—C24—C25—C30	−76.6 (4)
N2—C6—C7—C12	67.0 (5)	N6—C24—C25—C26	−79.8 (5)
C5—C6—C7—C12	−111.7 (4)	C23—C24—C25—C26	101.9 (4)
C12—C7—C8—C9	−0.4 (6)	C30—C25—C26—C27	0.4 (6)
C6—C7—C8—C9	179.4 (4)	C24—C25—C26—C27	−178.1 (4)
C7—C8—C9—C10	0.1 (6)	C25—C26—C27—C28	0.0 (7)
C8—C9—C10—C11	0.6 (6)	C26—C27—C28—C29	−0.6 (7)
C9—C10—C11—C12	−1.0 (6)	C27—C28—C29—C30	0.8 (7)
C10—C11—C12—C7	0.8 (6)	C26—C25—C30—C29	−0.2 (6)
C8—C7—C12—C11	−0.1 (6)	C24—C25—C30—C29	178.3 (4)
C6—C7—C12—C11	−179.8 (3)	C28—C29—C30—C25	−0.4 (6)
O1—C13—C14—N4	175.1 (3)	O2—C31—C32—N8	168.5 (3)
N3—C13—C14—N4	−5.0 (4)	N7—C31—C32—N8	−12.5 (5)
O1—C13—C14—C15	−4.8 (5)	O2—C31—C32—C33	−12.7 (5)
N3—C13—C14—C15	175.1 (3)	N7—C31—C32—C33	166.3 (3)
N4—C14—C15—C16	0.3 (5)	N8—C32—C33—C34	0.7 (5)
C13—C14—C15—C16	−179.8 (3)	C31—C32—C33—C34	−178.0 (3)
C14—C15—C16—C17	0.7 (5)	C32—C33—C34—C35	0.2 (5)
C15—C16—C17—C18	−0.9 (6)	C33—C34—C35—C36	−1.6 (6)
C16—C17—C18—N4	0.3 (6)	C34—C35—C36—N8	2.2 (6)
C2—C1—N1—C5	3.4 (5)	C20—C19—N5—C23	1.9 (5)
C2—C1—N1—Cd1	−162.4 (3)	C20—C19—N5—Cd2	−171.9 (3)
C4—C5—N1—C1	−3.3 (5)	C22—C23—N5—C19	−1.5 (5)
C6—C5—N1—C1	177.1 (3)	C24—C23—N5—C19	176.9 (3)
C4—C5—N1—Cd1	163.5 (3)	C22—C23—N5—Cd2	172.8 (3)
C6—C5—N1—Cd1	−16.2 (4)	C24—C23—N5—Cd2	−8.8 (4)
C7—C6—N2—N3	0.6 (5)	C23—C24—N6—N7	177.4 (3)
C5—C6—N2—N3	179.3 (3)	C25—C24—N6—N7	−0.9 (5)
C7—C6—N2—Cd1	−165.7 (3)	C23—C24—N6—Cd2	17.4 (4)
C5—C6—N2—Cd1	13.0 (4)	C25—C24—N6—Cd2	−160.9 (3)
O1—C13—N3—N2	−4.9 (5)	C24—N6—N7—C31	−175.4 (3)
C14—C13—N3—N2	175.2 (3)	Cd2—N6—N7—C31	−14.7 (4)
C6—N2—N3—C13	−179.2 (3)	O2—C31—N7—N6	−1.6 (5)
Cd1—N2—N3—C13	−12.2 (4)	C32—C31—N7—N6	179.4 (3)
C17—C18—N4—C14	0.6 (5)	C35—C36—N8—C32	−1.3 (6)
C15—C14—N4—C18	−0.9 (5)	C33—C32—N8—C36	−0.2 (5)
C13—C14—N4—C18	179.1 (3)	C31—C32—N8—C36	178.6 (3)
N3—C13—O1—Cd1	18.3 (4)	N7—C31—O2—Cd2	15.8 (4)
C14—C13—O1—Cd1	−161.9 (3)	C32—C31—O2—Cd2	−165.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N4	0.88	2.27	2.629 (4)	104
N7—H7···N8	0.88	2.28	2.640 (4)	104