(Cyclo­butane-1,1-dicarboxyl­ato-κ²O,O′)(di-2-pyridylamine-κ²N,N′)palladium(II)

In the title complex, [Pd(C₆H₆O₂)(C₁₀H₉N₃)], the Pd atom has a distorted cis-square-planar geometry defined by bidentate di-2-pyridylamine and cyclo­butane-1,1-dicarboxyl­ate ligands. The complexes inter­act with each other via N—H...O hydrogen bonds, forming a head-to-tail polymeric chain along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• Disorder in main residue
• R factor = 0.020
• wR factor = 0.074
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT390_ALERT_3_A Deviating Methyl C14A    X-C-H Bond Angle ......      91.50 Deg.

Author Response: 91.50Deg. is belong to C13-C14A-C15 and 90.20 Deg. is belong to C13-C14B-C15

PLAT390_ALERT_3_A Deviating Methyl C14B    X-C-H Bond Angle ......      90.20 Deg.

Author Response: 91.50Deg. is belong to C13-C14A-C15 and 90.20 Deg. is belong to C13-C14B-C15

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C14A
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

---

Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2005) and CRYSTALS (Betteridge et al., 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: CrystalStructure.

(Cyclobutane-1,1-dicarboxylato-κ²O,O')(di-2-pyridylamine- κ²N,N')palladium(II)

Crystal data

[Pd(C6H6O2)(C10H9N3)]	Z = 2
Mr = 419.73	F(000) = 420
Triclinic, P1	Dx = 1.844 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 9.115 (6) Å	Cell parameters from 7195 reflections
b = 9.698 (8) Å	θ = 3.0–27.5°
c = 10.227 (6) Å	µ = 1.25 mm^−1
α = 67.92 (3)°	T = 296 K
β = 67.30 (2)°	Platelet, yellow
γ = 71.21 (3)°	0.30 × 0.30 × 0.10 mm
V = 756.1 (9) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	3244 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.013
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
Tmin = 0.702, Tmax = 0.882	k = −12→12
7482 measured reflections	l = −13→13
3425 independent reflections

Refinement

Refinement on F^2	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.020	w = 1/[σ^2(Fo^2) + (0.0453P)^2 + 0.0721P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.074	(Δ/σ)max < 0.001
S = 1.27	Δρmax = 0.54 e Å^−3
3425 reflections	Δρmin = −0.49 e Å^−3
227 parameters

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 using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
Pd1	0.169224 (18)	0.375556 (16)	0.393389 (16)	0.02605 (8)
O1	0.2241 (2)	0.4938 (2)	0.48770 (19)	0.0367 (4)
O2	0.2902 (3)	0.7033 (2)	0.4643 (2)	0.0453 (4)
O3	0.1963 (3)	0.7820 (2)	0.0782 (2)	0.0483 (5)
O4	0.1313 (2)	0.56613 (19)	0.2316 (2)	0.0379 (4)
N1	0.1015 (2)	0.2661 (2)	0.3010 (2)	0.0282 (4)
N2	0.2479 (2)	0.0244 (2)	0.4058 (2)	0.0327 (4)
H5	0.3042	−0.0591	0.3854	0.039*
N3	0.2170 (2)	0.1812 (2)	0.5500 (2)	0.0276 (4)
C1	0.0044 (3)	0.3489 (3)	0.2129 (3)	0.0357 (5)
H1	−0.0392	0.4508	0.2090	0.043*
C2	−0.0319 (3)	0.2901 (3)	0.1304 (3)	0.0385 (5)
H2	−0.0964	0.3513	0.0696	0.046*
C3	0.0291 (3)	0.1366 (3)	0.1384 (3)	0.0377 (5)
H3	0.0077	0.0940	0.0817	0.045*
C4	0.1216 (3)	0.0495 (3)	0.2317 (3)	0.0362 (5)
H4	0.1619	−0.0536	0.2401	0.043*
C5	0.1547 (3)	0.1169 (2)	0.3139 (2)	0.0282 (4)
C6	0.2648 (3)	0.0447 (2)	0.5250 (2)	0.0276 (4)
C7	0.3362 (3)	−0.0838 (3)	0.6194 (3)	0.0343 (5)
H6	0.3755	−0.1761	0.5972	0.041*
C8	0.3478 (3)	−0.0724 (3)	0.7440 (3)	0.0384 (5)
H7	0.3959	−0.1566	0.8070	0.046*
C9	0.2872 (3)	0.0661 (3)	0.7759 (3)	0.0381 (5)
H8	0.2891	0.0749	0.8627	0.046*
C10	0.2247 (3)	0.1893 (3)	0.6773 (3)	0.0339 (5)
H9	0.1860	0.2825	0.6979	0.041*
C11	0.2859 (3)	0.6127 (2)	0.4091 (3)	0.0297 (4)
C12	0.3576 (3)	0.6365 (2)	0.2417 (3)	0.0298 (4)
C13	0.5033 (3)	0.5061 (3)	0.1996 (3)	0.0445 (6)
H13A	0.5175	0.4184	0.2833	0.053*
H13B	0.5025	0.4758	0.1197	0.053*
C14A	0.6161 (12)	0.6093 (14)	0.1521 (12)	0.067 (3)	0.50
H14A	0.6914	0.6150	0.0534	0.081*	0.50
H14B	0.6737	0.5873	0.2224	0.081*	0.50
C14B	0.6014 (12)	0.6315 (12)	0.0897 (9)	0.0517 (19)	0.50
H14C	0.7067	0.6152	0.1019	0.062*	0.50
H14D	0.6115	0.6497	−0.0131	0.062*	0.50
C15	0.4738 (3)	0.7484 (3)	0.1584 (3)	0.0417 (6)
H15A	0.4624	0.8122	0.0622	0.050*
H15B	0.4723	0.8084	0.2165	0.050*
C16	0.2197 (3)	0.6673 (2)	0.1765 (2)	0.0307 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.03318 (11)	0.01760 (10)	0.03135 (11)	−0.00700 (7)	−0.01305 (8)	−0.00642 (7)
O1	0.0565 (11)	0.0259 (8)	0.0339 (8)	−0.0160 (8)	−0.0147 (8)	−0.0080 (7)
O2	0.0746 (13)	0.0310 (9)	0.0431 (10)	−0.0207 (9)	−0.0208 (10)	−0.0130 (8)
O3	0.0732 (13)	0.0356 (10)	0.0461 (10)	−0.0221 (9)	−0.0367 (10)	0.0061 (8)
O4	0.0490 (10)	0.0238 (8)	0.0482 (10)	−0.0123 (7)	−0.0281 (8)	−0.0002 (7)
N1	0.0311 (9)	0.0229 (9)	0.0345 (9)	−0.0075 (7)	−0.0127 (8)	−0.0078 (7)
N2	0.0432 (10)	0.0210 (9)	0.0406 (10)	−0.0029 (8)	−0.0191 (9)	−0.0126 (8)
N3	0.0343 (9)	0.0212 (9)	0.0292 (9)	−0.0088 (7)	−0.0105 (8)	−0.0058 (7)
C1	0.0392 (12)	0.0266 (11)	0.0461 (13)	−0.0063 (9)	−0.0211 (11)	−0.0074 (10)
C2	0.0377 (12)	0.0427 (14)	0.0435 (13)	−0.0117 (10)	−0.0211 (11)	−0.0093 (11)
C3	0.0366 (12)	0.0458 (14)	0.0441 (13)	−0.0132 (10)	−0.0147 (11)	−0.0210 (11)
C4	0.0397 (12)	0.0314 (12)	0.0472 (13)	−0.0060 (10)	−0.0165 (11)	−0.0192 (11)
C5	0.0300 (10)	0.0251 (10)	0.0329 (10)	−0.0078 (8)	−0.0093 (9)	−0.0102 (9)
C6	0.0310 (10)	0.0225 (10)	0.0305 (10)	−0.0088 (8)	−0.0090 (9)	−0.0065 (8)
C7	0.0390 (12)	0.0235 (11)	0.0389 (12)	−0.0074 (9)	−0.0131 (10)	−0.0050 (9)
C8	0.0469 (13)	0.0301 (12)	0.0366 (12)	−0.0102 (10)	−0.0200 (11)	0.0015 (10)
C9	0.0490 (14)	0.0399 (13)	0.0304 (11)	−0.0166 (11)	−0.0145 (10)	−0.0066 (10)
C10	0.0438 (13)	0.0303 (12)	0.0323 (11)	−0.0120 (10)	−0.0107 (10)	−0.0111 (9)
C11	0.0371 (11)	0.0214 (10)	0.0356 (11)	−0.0056 (9)	−0.0163 (10)	−0.0085 (8)
C12	0.0353 (11)	0.0217 (10)	0.0348 (11)	−0.0054 (8)	−0.0133 (9)	−0.0084 (8)
C13	0.0454 (14)	0.0358 (13)	0.0492 (14)	0.0042 (11)	−0.0157 (12)	−0.0181 (12)
C14A	0.039 (4)	0.068 (6)	0.083 (7)	−0.007 (3)	−0.009 (5)	−0.023 (6)
C14B	0.042 (4)	0.058 (5)	0.048 (4)	−0.013 (3)	−0.004 (4)	−0.015 (4)
C15	0.0387 (13)	0.0410 (14)	0.0464 (14)	−0.0174 (11)	−0.0100 (11)	−0.0087 (11)
C16	0.0414 (12)	0.0227 (10)	0.0322 (10)	−0.0077 (9)	−0.0146 (10)	−0.0078 (8)

Geometric parameters (Å, º)

Pd1—O1	2.0169 (19)	C7—C8	1.366 (3)
Pd1—O4	2.001 (2)	C7—H6	0.9300
Pd1—N1	2.007 (2)	C8—C9	1.389 (4)
Pd1—N3	2.012 (2)	C8—H7	0.9300
O1—C11	1.291 (3)	C9—C10	1.367 (4)
O2—C11	1.227 (3)	C9—H8	0.9300
O3—C16	1.211 (3)	C10—H9	0.9300
O4—C16	1.293 (3)	C11—C12	1.532 (3)
N1—C5	1.341 (3)	C12—C16	1.539 (3)
N1—C1	1.362 (3)	C12—C15	1.541 (3)
N2—C6	1.377 (3)	C12—C13	1.560 (3)
N2—C5	1.378 (3)	C13—C14A	1.486 (13)
N2—H5	0.8600	C13—C14B	1.562 (11)
N3—C6	1.343 (3)	C13—H13A	0.9700
N3—C10	1.363 (3)	C13—H13B	0.9700
C1—C2	1.358 (4)	C14A—C15	1.542 (11)
C1—H1	0.9300	C14A—H14A	0.9700
C2—C3	1.394 (4)	C14A—H14B	0.9700
C2—H2	0.9300	C14B—C15	1.500 (11)
C3—C4	1.375 (3)	C14B—H14C	0.9700
C3—H3	0.9300	C14B—H14D	0.9700
C4—C5	1.401 (3)	C15—H15A	0.9700
C4—H4	0.9300	C15—H15B	0.9700
C6—C7	1.402 (3)
O1—Pd1—O4	89.60 (9)	N3—C10—H9	118.7
O1—Pd1—N1	176.60 (7)	C9—C10—H9	118.7
O1—Pd1—N3	90.90 (9)	O2—C11—O1	122.3 (2)
O4—Pd1—N1	88.71 (10)	O2—C11—C12	120.4 (2)
O4—Pd1—N3	177.47 (7)	O1—C11—C12	117.35 (19)
N1—Pd1—N3	90.92 (10)	C11—C12—C16	109.09 (19)
C11—O1—Pd1	121.20 (15)	C11—C12—C15	115.65 (19)
C16—O4—Pd1	122.66 (15)	C16—C12—C15	115.0 (2)
C5—N1—C1	118.0 (2)	C11—C12—C13	113.05 (19)
C5—N1—Pd1	123.49 (16)	C16—C12—C13	114.18 (19)
C1—N1—Pd1	118.39 (16)	C15—C12—C13	88.8 (2)
C6—N2—C5	130.2 (2)	C14A—C13—C12	89.2 (5)
C6—N2—H5	114.9	C12—C13—C14B	87.7 (4)
C5—N2—H5	114.9	C14A—C13—H13A	113.8
C6—N3—C10	118.3 (2)	C12—C13—H13A	113.8
C6—N3—Pd1	122.14 (16)	C14B—C13—H13A	135.8
C10—N3—Pd1	118.83 (16)	C14A—C13—H13B	113.8
C2—C1—N1	123.2 (2)	C12—C13—H13B	113.8
C2—C1—H1	118.4	C14B—C13—H13B	92.3
N1—C1—H1	118.4	H13A—C13—H13B	111.0
C1—C2—C3	118.9 (2)	C13—C14A—C15	91.5 (6)
C1—C2—H2	120.5	C13—C14A—H14A	113.4
C3—C2—H2	120.5	C15—C14A—H14A	113.4
C4—C3—C2	118.7 (2)	C13—C14A—H14B	113.4
C4—C3—H3	120.6	C15—C14A—H14B	113.4
C2—C3—H3	120.6	H14A—C14A—H14B	110.7
C3—C4—C5	119.6 (2)	C15—C14B—C13	90.2 (5)
C3—C4—H4	120.2	C15—C14B—H14C	113.6
C5—C4—H4	120.2	C13—C14B—H14C	113.6
N1—C5—N2	121.37 (19)	C15—C14B—H14D	113.6
N1—C5—C4	121.4 (2)	C13—C14B—H14D	113.6
N2—C5—C4	117.2 (2)	H14C—C14B—H14D	110.9
N3—C6—N2	121.9 (2)	C14B—C15—C12	90.7 (4)
N3—C6—C7	121.1 (2)	C14A—C15—C12	87.9 (5)
N2—C6—C7	117.0 (2)	C14B—C15—H15A	90.8
C8—C7—C6	119.6 (2)	C14A—C15—H15A	114.0
C8—C7—H6	120.2	C12—C15—H15A	114.0
C6—C7—H6	120.2	C14B—C15—H15B	133.7
C7—C8—C9	119.3 (2)	C14A—C15—H15B	114.0
C7—C8—H7	120.3	C12—C15—H15B	114.0
C9—C8—H7	120.3	H15A—C15—H15B	111.2
C10—C9—C8	118.8 (2)	O3—C16—O4	122.3 (2)
C10—C9—H8	120.6	O3—C16—C12	120.6 (2)
C8—C9—H8	120.6	O4—C16—C12	117.10 (19)
N3—C10—C9	122.6 (2)
O4—Pd1—O1—C11	−28.75 (19)	C6—N3—C10—C9	3.7 (3)
N3—Pd1—O1—C11	148.76 (19)	Pd1—N3—C10—C9	−166.75 (19)
N1—Pd1—O4—C16	−145.1 (2)	C8—C9—C10—N3	1.1 (4)
O1—Pd1—O4—C16	37.8 (2)	Pd1—O1—C11—O2	165.05 (19)
O4—Pd1—N1—C5	152.17 (19)	Pd1—O1—C11—C12	−15.9 (3)
N3—Pd1—N1—C5	−25.33 (19)	O2—C11—C12—C16	−114.7 (2)
O4—Pd1—N1—C1	−23.57 (19)	O1—C11—C12—C16	66.2 (3)
N3—Pd1—N1—C1	158.94 (19)	O2—C11—C12—C15	16.8 (3)
N1—Pd1—N3—C6	29.41 (18)	O1—C11—C12—C15	−162.3 (2)
O1—Pd1—N3—C6	−153.47 (18)	O2—C11—C12—C13	117.1 (3)
N1—Pd1—N3—C10	−160.57 (18)	O1—C11—C12—C13	−62.0 (3)
O1—Pd1—N3—C10	16.56 (18)	C11—C12—C13—C14A	−105.1 (5)
C5—N1—C1—C2	−4.5 (4)	C16—C12—C13—C14A	129.4 (5)
Pd1—N1—C1—C2	171.5 (2)	C15—C12—C13—C14A	12.4 (5)
N1—C1—C2—C3	1.7 (4)	C11—C12—C13—C14B	−129.3 (4)
C1—C2—C3—C4	1.2 (4)	C16—C12—C13—C14B	105.2 (4)
C2—C3—C4—C5	−1.2 (4)	C15—C12—C13—C14B	−11.9 (4)
C1—N1—C5—N2	−177.3 (2)	C12—C13—C14A—C15	−12.4 (5)
Pd1—N1—C5—N2	6.9 (3)	C12—C13—C14B—C15	12.2 (4)
C1—N1—C5—C4	4.4 (3)	C13—C14B—C15—C12	−12.3 (4)
Pd1—N1—C5—C4	−171.35 (18)	C13—C14A—C15—C12	12.5 (5)
C6—N2—C5—N1	20.9 (4)	C11—C12—C15—C14B	127.4 (4)
C6—N2—C5—C4	−160.8 (2)	C16—C12—C15—C14B	−103.9 (4)
C3—C4—C5—N1	−1.7 (4)	C13—C12—C15—C14B	12.3 (4)
C3—C4—C5—N2	180.0 (2)	C11—C12—C15—C14A	103.2 (5)
C10—N3—C6—N2	174.3 (2)	C16—C12—C15—C14A	−128.2 (5)
Pd1—N3—C6—N2	−15.6 (3)	C13—C12—C15—C14A	−11.9 (5)
C10—N3—C6—C7	−6.4 (3)	Pd1—O4—C16—O3	179.70 (19)
Pd1—N3—C6—C7	163.71 (17)	Pd1—O4—C16—C12	−0.5 (3)
C5—N2—C6—N3	−16.0 (4)	C11—C12—C16—O3	123.5 (2)
C5—N2—C6—C7	164.7 (2)	C15—C12—C16—O3	−8.4 (3)
N3—C6—C7—C8	4.3 (4)	C13—C12—C16—O3	−109.0 (3)
N2—C6—C7—C8	−176.3 (2)	C11—C12—C16—O4	−56.3 (3)
C6—C7—C8—C9	0.6 (4)	C15—C12—C16—O4	171.8 (2)
C7—C8—C9—C10	−3.2 (4)	C13—C12—C16—O4	71.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H5···O2^i	0.86	2.17	2.865 (4)	138

Symmetry code: (i) x, y−1, z.