Crystal structures of di­bromido­{N-[(pyridin-2-yl-κN)methyl­idene]picolinohydrazide-κ²N′,O}cadmium methanol monosolvate and di­iodido{N-[(pyridin-2-yl-κN)methyl­idene]picolinohydrazide-κ²N′,O}cadmium

The title compounds are cadmium bromide and cadmium iodide complexes of the ligand N′-(pyridin-2-yl­methyl­ene)picolinohydrazide. In both compounds, the Cd²⁺ ion is ligated by one O atom and two N atoms of the tridentate ligand, and by two halide ions. Both have fivefold coordination spheres with a distorted square-pyramidal geometry.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 130 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.034
• wR factor = 0.078
• Data-to-parameter ratio = 17.2

Structure: II

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.023
• wR factor = 0.058
• Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          3 Report

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         88 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Note

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: II


Alert level G
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I1A    --  Cd1     ..        9.7 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  I2A    --  Cd1     ..        6.7 s.u.
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Cd1    --  N2      ..        5.2 s.u.
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..         10 % Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         72 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Note

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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: CrysAlis PRO (Agilent, 2011) for (I); APEX3 (Bruker, 2016) for (II). Cell refinement: CrysAlis PRO (Agilent, 2011) for (I); SAINT-Plus (Bruker, 2016) for (II). Data reduction: CrysAlis PRO (Agilent, 2011) for (I); SAINT-Plus (Bruker, 2016) for (II). Program(s) used to solve structure: SHELXS2014/7 (Sheldrick, 2008) for (I); SHELXT (Sheldrick, 2015a) for (II). Program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b) for (I); SHELXL2014 (Sheldrick, 2015b) for (II). Molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) for (I); Mercury (Macrae et al., 2008) for (II). Software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009) for (I); SHELXL2014 (Sheldrick, 2015b) for (II).

(I) Dibromido{N-[(pyridin-2-yl-κN)methylidene]picolinohydrazide-κ²N',O}cadmium methanol monosolvate

Crystal data

[CdBr2(C12H10N4O)]·CH4O	F(000) = 1016
Mr = 530.50	Dx = 2.032 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.5418 Å
a = 7.5482 (4) Å	Cell parameters from 2435 reflections
b = 15.7571 (8) Å	θ = 3.0–74.4°
c = 14.6407 (6) Å	µ = 15.59 mm^−1
β = 95.132 (4)°	T = 130 K
V = 1734.35 (15) Å^3	Prism, light yellow
Z = 4	0.08 × 0.05 × 0.04 mm

Data collection

Agilent SuperNova, Dual, Cu at zero, Atlas diffractometer	3458 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2764 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
ω scans	θmax = 74.6°, θmin = 4.1°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −9→9
Tmin = 0.561, Tmax = 1.000	k = −18→19
6773 measured reflections	l = −18→10

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0275P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3458 reflections	Δρmax = 0.63 e Å^−3
201 parameters	Δρmin = −0.76 e Å^−3

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	0.3542 (9)	0.3896 (4)	0.5136 (4)	0.0494 (16)
H1	0.3566	0.4180	0.4565	0.059*
C2	0.2666 (9)	0.4292 (4)	0.5819 (4)	0.0482 (16)
H2	0.2058	0.4814	0.5708	0.058*
C3	0.2712 (8)	0.3898 (4)	0.6662 (3)	0.0376 (12)
H3	0.2154	0.4151	0.7150	0.045*
C4	0.3584 (7)	0.3128 (3)	0.6786 (3)	0.0315 (11)
H4	0.3643	0.2850	0.7364	0.038*
C5	0.4375 (6)	0.2763 (3)	0.6056 (3)	0.0259 (10)
C6	0.5190 (6)	0.1927 (3)	0.6130 (3)	0.0257 (9)
H6	0.5270	0.1620	0.6690	0.031*
C7	0.7080 (6)	0.0589 (3)	0.4588 (3)	0.0239 (9)
C8	0.7879 (6)	−0.0271 (3)	0.4567 (3)	0.0261 (10)
C9	0.8393 (6)	−0.0581 (3)	0.3740 (3)	0.0311 (11)
H9	0.8205	−0.0258	0.3192	0.037*
C10	0.9185 (7)	−0.1374 (4)	0.3737 (3)	0.0338 (11)
H10	0.9544	−0.1609	0.3185	0.041*
C11	0.9440 (6)	−0.1815 (3)	0.4546 (3)	0.0306 (11)
H11	1.0005	−0.2354	0.4566	0.037*
C12	0.8857 (7)	−0.1459 (3)	0.5335 (3)	0.0321 (11)
H12	0.9033	−0.1772	0.5890	0.039*
C13	0.2406 (12)	0.4864 (5)	0.2809 (5)	0.083 (3)
H13A	0.3593	0.5002	0.2631	0.124*
H13B	0.2374	0.4268	0.2999	0.124*
H13C	0.2133	0.5229	0.3321	0.124*
N1	0.4340 (6)	0.3153 (3)	0.5234 (3)	0.0333 (10)
N2	0.5791 (5)	0.1625 (3)	0.5414 (2)	0.0240 (8)
N3	0.6507 (5)	0.0828 (3)	0.5400 (2)	0.0265 (8)
H3N	0.6589	0.0495	0.5884	0.032*
N4	0.8071 (5)	−0.0709 (3)	0.5358 (2)	0.0267 (8)
O1	0.6971 (5)	0.1057 (2)	0.3907 (2)	0.0291 (7)
O2	0.1154 (6)	0.4997 (3)	0.2070 (2)	0.0401 (9)
H2A	0.1202	0.5505	0.1898	0.060*
Cd1	0.57044 (5)	0.24361 (2)	0.40754 (2)	0.02814 (10)
Br1	0.34115 (7)	0.21728 (4)	0.27099 (3)	0.03309 (13)
Br2	0.82753 (8)	0.34184 (4)	0.37807 (4)	0.03634 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.081 (5)	0.035 (4)	0.033 (3)	0.020 (3)	0.011 (3)	0.004 (2)
C2	0.076 (4)	0.028 (3)	0.041 (3)	0.024 (3)	0.012 (3)	−0.003 (2)
C3	0.049 (3)	0.027 (3)	0.038 (3)	0.003 (2)	0.009 (2)	−0.011 (2)
C4	0.042 (3)	0.024 (3)	0.029 (2)	−0.004 (2)	0.006 (2)	−0.001 (2)
C5	0.031 (2)	0.021 (3)	0.026 (2)	−0.003 (2)	0.0001 (17)	−0.0046 (18)
C6	0.031 (2)	0.022 (3)	0.024 (2)	−0.003 (2)	0.0019 (17)	0.0018 (18)
C7	0.022 (2)	0.017 (2)	0.032 (2)	−0.0017 (18)	−0.0005 (17)	−0.0006 (19)
C8	0.026 (2)	0.023 (3)	0.029 (2)	−0.0033 (19)	−0.0015 (17)	−0.0036 (19)
C9	0.031 (2)	0.032 (3)	0.030 (2)	0.003 (2)	0.0019 (19)	−0.001 (2)
C10	0.034 (3)	0.030 (3)	0.039 (3)	0.002 (2)	0.008 (2)	−0.001 (2)
C11	0.027 (2)	0.020 (3)	0.045 (3)	0.0005 (19)	0.003 (2)	−0.002 (2)
C12	0.031 (2)	0.025 (3)	0.039 (2)	0.000 (2)	0.001 (2)	0.003 (2)
C13	0.123 (8)	0.050 (5)	0.065 (4)	0.023 (5)	−0.045 (5)	−0.006 (4)
N1	0.050 (3)	0.025 (2)	0.0260 (18)	0.004 (2)	0.0066 (17)	−0.0026 (17)
N2	0.0269 (19)	0.023 (2)	0.0222 (16)	−0.0018 (16)	0.0007 (14)	−0.0002 (15)
N3	0.033 (2)	0.021 (2)	0.0258 (18)	0.0001 (17)	0.0004 (15)	0.0017 (16)
N4	0.0272 (19)	0.024 (2)	0.0295 (18)	0.0008 (17)	0.0035 (15)	−0.0002 (16)
O1	0.0388 (19)	0.0215 (19)	0.0274 (16)	0.0022 (15)	0.0046 (13)	0.0044 (14)
O2	0.060 (2)	0.032 (2)	0.0284 (17)	0.0022 (19)	0.0041 (16)	−0.0001 (15)
Cd1	0.03855 (18)	0.0225 (2)	0.02370 (15)	0.00179 (15)	0.00451 (12)	0.00180 (13)
Br1	0.0344 (3)	0.0331 (3)	0.0313 (2)	−0.0030 (2)	0.00060 (19)	0.0069 (2)
Br2	0.0439 (3)	0.0243 (3)	0.0413 (3)	−0.0036 (2)	0.0063 (2)	−0.0008 (2)

Geometric parameters (Å, º)

C1—N1	1.319 (7)	C9—H9	0.9500
C1—C2	1.394 (7)	C10—C11	1.370 (7)
C1—H1	0.9500	C10—H10	0.9500
C2—C3	1.378 (8)	C11—C12	1.391 (7)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.385 (8)	C12—N4	1.324 (7)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.395 (6)	C13—O2	1.388 (7)
C4—H4	0.9500	C13—H13A	0.9800
C5—N1	1.349 (6)	C13—H13B	0.9800
C5—C6	1.453 (7)	C13—H13C	0.9800
C6—N2	1.271 (6)	N1—Cd1	2.351 (4)
C6—H6	0.9500	N2—N3	1.368 (6)
C7—O1	1.236 (5)	N2—Cd1	2.336 (4)
C7—N3	1.354 (6)	N3—H3N	0.8800
C7—C8	1.485 (7)	O1—Cd1	2.396 (3)
C8—N4	1.344 (6)	O2—H2A	0.8400
C8—C9	1.393 (6)	Cd1—Br2	2.5490 (7)
C9—C10	1.385 (7)	Cd1—Br1	2.5585 (6)
N1—C1—C2	124.1 (5)	C12—C11—H11	120.6
N1—C1—H1	118.0	N4—C12—C11	123.9 (5)
C2—C1—H1	118.0	N4—C12—H12	118.1
C3—C2—C1	117.7 (5)	C11—C12—H12	118.1
C3—C2—H2	121.1	O2—C13—H13A	109.5
C1—C2—H2	121.1	O2—C13—H13B	109.5
C2—C3—C4	119.1 (5)	H13A—C13—H13B	109.5
C2—C3—H3	120.5	O2—C13—H13C	109.5
C4—C3—H3	120.5	H13A—C13—H13C	109.5
C3—C4—C5	119.4 (5)	H13B—C13—H13C	109.5
C3—C4—H4	120.3	C1—N1—C5	118.3 (4)
C5—C4—H4	120.3	C1—N1—Cd1	125.0 (3)
N1—C5—C4	121.3 (5)	C5—N1—Cd1	116.7 (3)
N1—C5—C6	117.0 (4)	C6—N2—N3	121.8 (4)
C4—C5—C6	121.6 (4)	C6—N2—Cd1	120.1 (3)
N2—C6—C5	117.3 (4)	N3—N2—Cd1	118.1 (3)
N2—C6—H6	121.4	C7—N3—N2	115.3 (4)
C5—C6—H6	121.4	C7—N3—H3N	122.4
O1—C7—N3	122.6 (4)	N2—N3—H3N	122.4
O1—C7—C8	121.7 (4)	C12—N4—C8	116.7 (4)
N3—C7—C8	115.7 (4)	C7—O1—Cd1	117.1 (3)
N4—C8—C9	123.5 (5)	C13—O2—H2A	109.5
N4—C8—C7	117.6 (4)	N2—Cd1—N1	68.80 (14)
C9—C8—C7	118.9 (4)	N2—Cd1—O1	66.95 (12)
C10—C9—C8	118.2 (5)	N1—Cd1—O1	135.60 (13)
C10—C9—H9	120.9	N2—Cd1—Br2	120.65 (9)
C8—C9—H9	120.9	N1—Cd1—Br2	102.70 (12)
C11—C10—C9	118.8 (5)	O1—Cd1—Br2	102.51 (8)
C11—C10—H10	120.6	N2—Cd1—Br1	122.22 (9)
C9—C10—H10	120.6	N1—Cd1—Br1	109.42 (11)
C10—C11—C12	118.9 (5)	O1—Cd1—Br1	91.20 (8)
C10—C11—H11	120.6	Br2—Cd1—Br1	115.99 (2)
N1—C1—C2—C3	3.2 (11)	C2—C1—N1—Cd1	176.8 (5)
C1—C2—C3—C4	−1.3 (10)	C4—C5—N1—C1	0.4 (8)
C2—C3—C4—C5	−0.8 (8)	C6—C5—N1—C1	177.2 (5)
C3—C4—C5—N1	1.4 (8)	C4—C5—N1—Cd1	−179.2 (4)
C3—C4—C5—C6	−175.4 (5)	C6—C5—N1—Cd1	−2.3 (6)
N1—C5—C6—N2	−0.6 (7)	C5—C6—N2—N3	−176.9 (4)
C4—C5—C6—N2	176.2 (5)	C5—C6—N2—Cd1	3.4 (6)
O1—C7—C8—N4	174.9 (4)	O1—C7—N3—N2	0.2 (6)
N3—C7—C8—N4	−4.3 (6)	C8—C7—N3—N2	179.3 (4)
O1—C7—C8—C9	−5.0 (7)	C6—N2—N3—C7	179.5 (4)
N3—C7—C8—C9	175.9 (4)	Cd1—N2—N3—C7	−0.8 (5)
N4—C8—C9—C10	−1.7 (7)	C11—C12—N4—C8	−1.6 (7)
C7—C8—C9—C10	178.1 (4)	C9—C8—N4—C12	2.7 (7)
C8—C9—C10—C11	−0.5 (7)	C7—C8—N4—C12	−177.1 (4)
C9—C10—C11—C12	1.5 (7)	N3—C7—O1—Cd1	0.5 (6)
C10—C11—C12—N4	−0.5 (8)	C8—C7—O1—Cd1	−178.6 (3)
C2—C1—N1—C5	−2.7 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2^i	0.88	1.96	2.803 (5)	161
O2—H2A···Br1^ii	0.84	2.70	3.456 (4)	150
C2—H2···Br2^iii	0.95	2.90	3.734 (6)	147
C4—H4···Br2^iv	0.95	2.91	3.826 (5)	162
C10—H10···Br1^v	0.95	2.85	3.703 (5)	149

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

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

Crystal data

[CdI2(C12H10N4O)]	F(000) = 1088
Mr = 592.44	Dx = 2.409 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.5264 (7) Å	Cell parameters from 6468 reflections
b = 13.1325 (12) Å	θ = 2.5–28.0°
c = 16.5718 (15) Å	µ = 5.12 mm^−1
β = 94.384 (1)°	T = 296 K
V = 1633.2 (3) Å^3	Plate, light yellow
Z = 4	0.48 × 0.20 × 0.02 mm

Data collection

Bruker D8 Venture diffractometer with Photon 100 CMOS detector	3946 independent reflections
Radiation source: fine-focus sealed tube	3193 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.3 pixels mm^-1	θmax = 28.2°, θmin = 2.0°
Sets of exposures each taken over 0.5° ω rotation scans	h = −9→10
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −17→17
Tmin = 0.616, Tmax = 0.903	l = −21→21
3946 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.058	w = 1/[σ^2(Fo^2) + (0.0256P)^2 + 0.6207P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
3946 reflections	Δρmax = 0.65 e Å^−3
204 parameters	Δρmin = −0.39 e Å^−3

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	Occ. (<1)
C1	0.5553 (5)	0.3164 (3)	0.9481 (2)	0.0622 (9)
H1	0.5027	0.2525	0.9506	0.075*
C2	0.6695 (5)	0.3481 (3)	1.0130 (2)	0.0691 (10)
H2	0.6933	0.3064	1.0578	0.083*
C3	0.7462 (5)	0.4426 (3)	1.0092 (2)	0.0662 (9)
H3	0.8220	0.4664	1.0520	0.079*
C4	0.7095 (4)	0.5017 (3)	0.9414 (2)	0.0591 (8)
H4	0.7609	0.5657	0.9376	0.071*
C5	0.5948 (4)	0.4646 (2)	0.87896 (18)	0.0481 (7)
C6	0.5559 (4)	0.5222 (2)	0.80398 (18)	0.0503 (7)
H6	0.5999	0.5879	0.7986	0.060*
C7	0.3276 (4)	0.4766 (2)	0.61592 (18)	0.0488 (7)
C8	0.2989 (4)	0.5342 (2)	0.53845 (18)	0.0498 (7)
C9	0.2074 (5)	0.4925 (3)	0.4719 (2)	0.0635 (9)
H9	0.1609	0.4269	0.4732	0.076*
C10	0.1865 (5)	0.5520 (3)	0.4020 (2)	0.0695 (10)
H10	0.1230	0.5271	0.3558	0.083*
C11	0.2590 (5)	0.6460 (3)	0.4019 (2)	0.0692 (10)
H11	0.2461	0.6865	0.3558	0.083*
C12	0.3516 (6)	0.6809 (3)	0.4704 (2)	0.0727 (11)
H12	0.4031	0.7453	0.4695	0.101 (15)*
N1	0.5174 (3)	0.3727 (2)	0.88258 (15)	0.0496 (6)
N2	0.4609 (3)	0.48064 (19)	0.74667 (15)	0.0473 (6)
N3	0.4243 (4)	0.5284 (2)	0.67483 (16)	0.0508 (6)
H3N	0.461 (5)	0.590 (3)	0.668 (2)	0.061*
N4	0.3717 (5)	0.6265 (2)	0.53900 (18)	0.0659 (8)
O1	0.2696 (3)	0.39087 (18)	0.62576 (14)	0.0592 (6)
Cd1	0.32992 (3)	0.32196 (2)	0.76532 (2)	0.05080 (8)
I1A	0.4779 (3)	0.1408 (2)	0.7239 (2)	0.0549 (3)	0.75 (2)
I2A	−0.0093 (3)	0.31832 (13)	0.81000 (15)	0.0555 (4)	0.75 (2)
I1B	0.4749 (10)	0.1451 (7)	0.7364 (9)	0.0654 (16)	0.25 (2)
I2B	0.0012 (11)	0.3249 (6)	0.8180 (7)	0.0787 (18)	0.25 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.071 (2)	0.060 (2)	0.055 (2)	0.0027 (17)	0.0032 (17)	0.0053 (16)
C2	0.073 (2)	0.081 (3)	0.053 (2)	0.018 (2)	−0.0004 (17)	0.0083 (18)
C3	0.058 (2)	0.088 (3)	0.0519 (19)	0.0085 (19)	−0.0055 (15)	−0.0109 (18)
C4	0.0529 (18)	0.065 (2)	0.0587 (19)	−0.0021 (16)	0.0016 (15)	−0.0105 (16)
C5	0.0423 (15)	0.0520 (18)	0.0500 (16)	0.0055 (13)	0.0039 (12)	−0.0044 (13)
C6	0.0490 (17)	0.0468 (18)	0.0551 (18)	−0.0015 (13)	0.0048 (13)	−0.0003 (14)
C7	0.0480 (16)	0.0503 (18)	0.0485 (16)	0.0069 (13)	0.0062 (13)	−0.0016 (13)
C8	0.0491 (17)	0.0503 (17)	0.0502 (17)	0.0049 (13)	0.0059 (13)	0.0020 (13)
C9	0.067 (2)	0.065 (2)	0.058 (2)	−0.0120 (17)	0.0011 (16)	−0.0026 (17)
C10	0.071 (2)	0.088 (3)	0.0490 (19)	−0.004 (2)	−0.0041 (16)	0.0038 (18)
C11	0.075 (2)	0.077 (3)	0.055 (2)	0.006 (2)	0.0017 (17)	0.0150 (18)
C12	0.096 (3)	0.058 (2)	0.063 (2)	−0.003 (2)	−0.001 (2)	0.0137 (18)
N1	0.0526 (15)	0.0482 (15)	0.0478 (14)	0.0044 (11)	0.0029 (11)	−0.0017 (11)
N2	0.0469 (14)	0.0479 (15)	0.0473 (13)	0.0069 (11)	0.0043 (11)	0.0008 (11)
N3	0.0601 (16)	0.0426 (14)	0.0494 (14)	0.0027 (12)	0.0028 (12)	0.0037 (11)
N4	0.088 (2)	0.0536 (18)	0.0547 (17)	−0.0011 (15)	−0.0024 (15)	0.0027 (13)
O1	0.0695 (15)	0.0508 (13)	0.0565 (13)	−0.0077 (11)	−0.0013 (11)	0.0046 (10)
Cd1	0.05478 (14)	0.04400 (13)	0.05349 (14)	−0.00171 (9)	0.00328 (10)	−0.00142 (9)
I1A	0.0610 (5)	0.0468 (4)	0.0568 (7)	0.0081 (3)	0.0034 (5)	−0.0055 (4)
I2A	0.0516 (5)	0.0512 (7)	0.0641 (5)	0.0071 (3)	0.0069 (4)	0.0103 (3)
I1B	0.0736 (17)	0.0486 (12)	0.077 (4)	0.0009 (11)	0.0232 (18)	−0.0098 (15)
I2B	0.065 (2)	0.097 (3)	0.077 (2)	0.0126 (15)	0.0233 (17)	0.0117 (15)

Geometric parameters (Å, º)

C1—N1	1.326 (4)	C9—C10	1.396 (5)
C1—C2	1.389 (5)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.350 (6)
C2—C3	1.372 (6)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.365 (6)
C3—C4	1.376 (5)	C11—H11	0.9300
C3—H3	0.9300	C12—N4	1.341 (5)
C4—C5	1.384 (5)	C12—H12	0.9300
C4—H4	0.9300	N1—Cd1	2.407 (3)
C5—N1	1.343 (4)	N2—N3	1.355 (4)
C5—C6	1.465 (4)	N2—Cd1	2.336 (3)
C6—N2	1.268 (4)	N3—H3N	0.86 (4)
C6—H6	0.9300	O1—Cd1	2.493 (2)
C7—O1	1.223 (4)	Cd1—I1B	2.626 (10)
C7—N3	1.355 (4)	Cd1—I2B	2.687 (6)
C7—C8	1.492 (4)	Cd1—I2A	2.7128 (19)
C8—N4	1.329 (4)	Cd1—I1A	2.736 (3)
C8—C9	1.370 (5)
N1—C1—C2	123.2 (4)	C12—C11—H11	120.4
N1—C1—H1	118.4	N4—C12—C11	122.9 (4)
C2—C1—H1	118.4	N4—C12—H12	118.6
C3—C2—C1	118.3 (4)	C11—C12—H12	118.6
C3—C2—H2	120.8	C1—N1—C5	118.1 (3)
C1—C2—H2	120.8	C1—N1—Cd1	125.6 (2)
C2—C3—C4	119.2 (3)	C5—N1—Cd1	116.3 (2)
C2—C3—H3	120.4	C6—N2—N3	121.6 (3)
C4—C3—H3	120.4	C6—N2—Cd1	120.3 (2)
C3—C4—C5	119.1 (4)	N3—N2—Cd1	118.0 (2)
C3—C4—H4	120.5	N2—N3—C7	117.6 (3)
C5—C4—H4	120.5	N2—N3—H3N	120 (2)
N1—C5—C4	122.1 (3)	C7—N3—H3N	122 (2)
N1—C5—C6	116.3 (3)	C8—N4—C12	117.4 (3)
C4—C5—C6	121.6 (3)	C7—O1—Cd1	114.6 (2)
N2—C6—C5	118.5 (3)	N2—Cd1—N1	68.43 (9)
N2—C6—H6	120.7	N2—Cd1—O1	66.56 (8)
C5—C6—H6	120.7	N1—Cd1—O1	134.63 (8)
O1—C7—N3	122.9 (3)	N2—Cd1—I1B	125.4 (2)
O1—C7—C8	123.5 (3)	N1—Cd1—I1B	99.6 (3)
N3—C7—C8	113.6 (3)	O1—Cd1—I1B	101.6 (3)
N4—C8—C9	123.5 (3)	N2—Cd1—I2B	116.02 (18)
N4—C8—C7	115.1 (3)	N1—Cd1—I2B	103.4 (3)
C9—C8—C7	121.4 (3)	O1—Cd1—I2B	100.9 (2)
C8—C9—C10	117.5 (3)	I1B—Cd1—I2B	118.5 (2)
C8—C9—H9	121.3	N2—Cd1—I2A	117.87 (7)
C10—C9—H9	121.3	N1—Cd1—I2A	106.89 (9)
C11—C10—C9	119.5 (4)	O1—Cd1—I2A	98.69 (7)
C11—C10—H10	120.2	N2—Cd1—I1A	123.94 (9)
C9—C10—H10	120.2	N1—Cd1—I1A	102.63 (9)
C10—C11—C12	119.2 (4)	O1—Cd1—I1A	97.56 (9)
C10—C11—H11	120.4	I2A—Cd1—I1A	117.57 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···I2A^i	0.87 (4)	3.04 (4)	3.866 (3)	161 (3)

Symmetry code: (i) −x+1/2, y+1/2, −z+3/2.