trans-Bis[(S)-(−)-2-aminomethyl-1-ethylpyrrolidine-κ²N]palladium(II) dichloride methanol trisolvate

The crystal structure of the title compound, [Pd(C₇H₁₆N₂)₂]Cl₂·3CH₃OH, has been determined at 180 (2) K in the non-centrosymmetric space group P2₁2₁2₁. The structure contains only one crystallographically unique Pd metal centre, showing a slightly distorted square-planar geometry, in which the two chiral (S)-(−)-2-amino­methyl-1-ethyl­pyrrolidine di­amines are coordinated with a trans configuration in order to minimize the steric interaction between neighbouring substituent ethyl groups. [Pd(C₇H₁₆N₂)₂]²⁺ complex cations are strongly hydrogen-bonded to the Cl⁻ anions and methanol mol­ecules, forming supramolecular tapes running along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 180 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.036
• wR factor = 0.075
• Data-to-parameter ratio = 21.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.98

Alert level B
PLAT415_ALERT_2_B Short Inter D-H..H-X       H4C    ..  H17F     =       2.06 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      20.00 Perc.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              C H4 O

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.45
           From the CIF: _reflns_number_total               5324
           Count of symmetry unique reflns         3239
           Completeness (_total/calc)            164.37%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2085
           Fraction of Friedel pairs measured     0.644
           Are heavy atom types Z>Si present          yes

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

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

trans-Bis[(S)-(-)-2-aminomethyl-1-ethylpyrrolidine-κ²N]palladium(II) dichloride methanol trisolvate

Crystal data

[Pd(C7H16N2)2]Cl2·3CH4O	F(000) = 1112
Mr = 529.86	Dx = 1.417 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 14842 reflections
a = 7.3092 (1) Å	θ = 1.0–27.5°
b = 12.9075 (2) Å	µ = 0.99 mm^−1
c = 26.3277 (6) Å	T = 180 K
V = 2483.85 (8) Å^3	Block, yellow
Z = 4	0.23 × 0.10 × 0.10 mm

Data collection

Nonius Kappa CCD area-detector diffractometer	4721 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
thin slice ω and φ scans	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −9→9
Tmin = 0.843, Tmax = 0.906	k = −16→16
14487 measured reflections	l = −29→34
5324 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.075	w = 1/[σ^2(Fo^2) + (0.0286P)^2 + 1.4529P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.002
5324 reflections	Δρmax = 0.52 e Å^−3
243 parameters	Δρmin = −1.10 e Å^−3
0 restraints	Absolute structure: Flack (1983), 2149 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.02 (3)

Special details

Experimental. -OH hydrogen atoms were not located in difference Fourier maps and were instead placed in calculated positions with AFIX 14 instructions.

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	Occ. (<1)
Pd1	0.45964 (3)	0.68757 (2)	0.129037 (10)	0.01785 (7)
Cl1	0.86106 (13)	0.04170 (8)	0.23553 (4)	0.0327 (2)
Cl2	0.90153 (12)	0.61434 (8)	0.02073 (4)	0.0316 (2)
N1	0.4681 (4)	0.8453 (2)	0.13970 (10)	0.0185 (6)
C1	0.8075 (5)	0.8488 (3)	0.12406 (18)	0.0323 (10)
H1A	0.9040	0.8880	0.1067	0.048*
H1B	0.8048	0.7778	0.1109	0.048*
H1C	0.8323	0.8475	0.1606	0.048*
N2	0.4355 (4)	0.6835 (2)	0.20626 (10)	0.0225 (6)
H2A	0.3571	0.6313	0.2158	0.027*
H2B	0.5478	0.6713	0.2209	0.027*
C2	0.6253 (5)	0.8999 (3)	0.11461 (16)	0.0255 (9)
H2C	0.6304	0.9721	0.1272	0.031*
H2D	0.6030	0.9025	0.0775	0.031*
N3	0.4224 (4)	0.5312 (2)	0.11751 (11)	0.0212 (7)
C3	0.2921 (5)	0.8920 (3)	0.12177 (16)	0.0242 (9)
H3A	0.1879	0.8455	0.1295	0.029*
H3B	0.2959	0.9045	0.0847	0.029*
N4	0.4974 (3)	0.6908 (2)	0.05212 (10)	0.0209 (6)
H4A	0.4475	0.7502	0.0387	0.025*
H4B	0.6203	0.6898	0.0446	0.025*
C4	0.2737 (5)	0.9943 (3)	0.15075 (15)	0.0300 (9)
H4C	0.3316	1.0516	0.1316	0.036*
H4D	0.1433	1.0115	0.1565	0.036*
C5	0.3721 (5)	0.9766 (3)	0.20123 (15)	0.0297 (9)
H5A	0.2835	0.9757	0.2297	0.036*
H5B	0.4630	1.0320	0.2075	0.036*
C6	0.4680 (5)	0.8702 (3)	0.19618 (13)	0.0216 (7)
H6	0.5961	0.8742	0.2093	0.026*
C7	0.3630 (5)	0.7854 (3)	0.22326 (14)	0.0256 (9)
H7A	0.3778	0.7926	0.2605	0.031*
H7B	0.2311	0.7906	0.2151	0.031*
C8	0.7377 (5)	0.4915 (3)	0.15137 (16)	0.0331 (10)
H8A	0.8048	0.4429	0.1731	0.050*
H8B	0.7531	0.5621	0.1644	0.050*
H8C	0.7854	0.4876	0.1166	0.050*
C9	0.5354 (5)	0.4634 (3)	0.15137 (14)	0.0263 (8)
H9A	0.5218	0.3905	0.1402	0.032*
H9B	0.4880	0.4685	0.1865	0.032*
C10	0.2238 (5)	0.5038 (3)	0.12357 (17)	0.0258 (8)
H10A	0.1451	0.5604	0.1106	0.031*
H10B	0.1940	0.4918	0.1598	0.031*
C11	0.1951 (6)	0.4051 (3)	0.09266 (16)	0.0340 (10)
H11A	0.0705	0.4032	0.0780	0.041*
H11B	0.2126	0.3429	0.1142	0.041*
C12	0.3395 (6)	0.4096 (3)	0.05078 (16)	0.0337 (10)
H12A	0.2806	0.4162	0.0171	0.040*
H12B	0.4151	0.3459	0.0510	0.040*
C13	0.4581 (5)	0.5052 (3)	0.06218 (13)	0.0223 (7)
H13	0.5903	0.4882	0.0571	0.027*
C14	0.4063 (5)	0.5983 (3)	0.03029 (15)	0.0242 (8)
H14A	0.4463	0.5879	−0.0053	0.029*
H14B	0.2719	0.6078	0.0305	0.029*
C15	1.1732 (6)	0.2558 (4)	0.2127 (2)	0.0458 (12)
H15A	1.1593	0.3290	0.2218	0.055*
H15B	1.0679	0.2338	0.1923	0.055*
H15C	1.2856	0.2467	0.1929	0.055*
O1	1.1830 (4)	0.1947 (3)	0.25769 (11)	0.0411 (7)
H1	1.1013	0.1490	0.2569	0.049*
C16	0.7675 (7)	0.1925 (5)	0.1078 (2)	0.0575 (13)
H16A	0.8281	0.2600	0.1050	0.069*
H16B	0.6840	0.1831	0.0790	0.069*
H16C	0.8598	0.1374	0.1075	0.069*
O2	0.6691 (5)	0.1881 (3)	0.15290 (15)	0.0704 (11)
H2	0.7239	0.1496	0.1736	0.084*
C17	0.7291 (8)	0.3567 (5)	0.9689 (3)	0.0661 (11)*	0.50
H17A	0.6901	0.3154	0.9982	0.079*	0.50
H17B	0.7197	0.3147	0.9379	0.079*	0.50
H17C	0.6504	0.4178	0.9657	0.079*	0.50
O3	0.9132 (10)	0.3886 (6)	0.9758 (3)	0.0661 (11)*	0.50
H3	0.9179	0.4342	0.9985	0.079*	0.50
C17'	0.7291 (8)	0.3567 (5)	0.9689 (3)	0.0661 (11)*	0.50
H17D	0.6040	0.3744	0.9790	0.079*	0.50
H17E	0.7328	0.2847	0.9571	0.079*	0.50
H17F	0.7683	0.4027	0.9413	0.079*	0.50
O3'	0.8417 (10)	0.3681 (6)	1.0087 (3)	0.0661 (11)*	0.50
H3'	0.9014	0.4233	1.0055	0.079*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.01594 (12)	0.01959 (13)	0.01803 (12)	−0.00027 (11)	0.00031 (11)	0.00015 (13)
Cl1	0.0293 (5)	0.0354 (6)	0.0334 (5)	−0.0040 (4)	0.0063 (4)	−0.0062 (5)
Cl2	0.0254 (5)	0.0362 (6)	0.0334 (5)	0.0024 (4)	0.0042 (4)	0.0104 (5)
N1	0.0151 (13)	0.0190 (14)	0.0215 (15)	−0.0010 (12)	0.0027 (12)	−0.0014 (12)
C1	0.0198 (19)	0.044 (3)	0.033 (2)	−0.0045 (16)	0.0013 (17)	−0.003 (2)
N2	0.0248 (16)	0.0233 (16)	0.0195 (14)	−0.0014 (16)	0.0008 (12)	−0.0013 (15)
C2	0.0207 (19)	0.028 (2)	0.028 (2)	−0.0066 (15)	0.0046 (15)	0.0028 (18)
N3	0.0217 (16)	0.0215 (16)	0.0204 (16)	−0.0011 (11)	0.0004 (12)	0.0016 (13)
C3	0.0174 (18)	0.027 (2)	0.029 (2)	0.0056 (15)	−0.0029 (16)	−0.0010 (19)
N4	0.0212 (16)	0.0218 (15)	0.0197 (14)	0.0022 (13)	0.0023 (10)	0.0022 (15)
C4	0.029 (2)	0.028 (2)	0.033 (2)	0.0106 (17)	−0.0019 (17)	−0.002 (2)
C5	0.032 (2)	0.029 (2)	0.028 (2)	0.0028 (18)	0.0013 (17)	−0.0060 (19)
C6	0.0196 (16)	0.0251 (19)	0.0201 (17)	−0.0008 (17)	−0.0016 (16)	−0.0024 (16)
C7	0.0273 (19)	0.030 (2)	0.0197 (19)	0.0031 (16)	0.0014 (15)	−0.0020 (17)
C8	0.030 (2)	0.037 (3)	0.033 (2)	0.0056 (18)	−0.0033 (18)	0.001 (2)
C9	0.0306 (19)	0.0218 (19)	0.0266 (18)	0.0040 (18)	−0.0030 (18)	0.0026 (16)
C10	0.0218 (19)	0.031 (2)	0.025 (2)	−0.0057 (15)	0.0041 (17)	−0.0011 (19)
C11	0.035 (2)	0.036 (3)	0.031 (2)	−0.0155 (18)	0.0043 (18)	−0.002 (2)
C12	0.042 (2)	0.029 (2)	0.029 (2)	−0.0080 (18)	0.0054 (18)	−0.005 (2)
C13	0.0201 (16)	0.0251 (19)	0.0218 (17)	−0.0024 (17)	0.0021 (17)	−0.0026 (16)
C14	0.025 (2)	0.027 (2)	0.0202 (18)	−0.0019 (14)	0.0008 (14)	−0.0037 (17)
C15	0.050 (3)	0.035 (3)	0.052 (3)	−0.009 (2)	−0.021 (2)	0.007 (2)
O1	0.0420 (16)	0.0391 (18)	0.0424 (18)	−0.0111 (14)	−0.0157 (13)	0.0078 (17)
C16	0.072 (3)	0.054 (3)	0.046 (3)	−0.011 (3)	0.005 (3)	0.005 (3)
O2	0.078 (3)	0.077 (3)	0.057 (2)	0.020 (2)	0.0108 (19)	0.013 (2)

Geometric parameters (Å, º)

Pd1—N2	2.041 (3)	C8—C9	1.522 (6)
Pd1—N4	2.044 (3)	C8—H8A	0.980
Pd1—N1	2.056 (3)	C8—H8B	0.980
Pd1—N3	2.059 (3)	C8—H8C	0.980
N1—C3	1.496 (4)	C9—H9A	0.990
N1—C2	1.501 (4)	C9—H9B	0.990
N1—C6	1.521 (4)	C10—C11	1.527 (6)
C1—C2	1.507 (5)	C10—H10A	0.990
C1—H1A	0.980	C10—H10B	0.990
C1—H1B	0.980	C11—C12	1.527 (5)
C1—H1C	0.980	C11—H11A	0.990
N2—C7	1.487 (4)	C11—H11B	0.990
N2—H2A	0.920	C12—C13	1.539 (5)
N2—H2B	0.920	C12—H12A	0.990
C2—H2C	0.990	C12—H12B	0.990
C2—H2D	0.990	C13—C14	1.513 (5)
N3—C9	1.498 (4)	C13—H13	1.000
N3—C10	1.503 (5)	C14—H14A	0.990
N3—C13	1.517 (4)	C14—H14B	0.990
C3—C4	1.532 (5)	C15—O1	1.425 (5)
C3—H3A	0.990	C15—H15A	0.980
C3—H3B	0.990	C15—H15B	0.980
N4—C14	1.484 (4)	C15—H15C	0.980
N4—H4A	0.920	O1—H1	0.840
N4—H4B	0.920	C16—O2	1.390 (6)
C4—C5	1.529 (5)	C16—H16A	0.980
C4—H4C	0.990	C16—H16B	0.980
C4—H4D	0.990	C16—H16C	0.980
C5—C6	1.547 (5)	O2—H2	0.840
C5—H5A	0.990	C17—O3	1.419 (9)
C5—H5B	0.990	C17—H17A	0.980
C6—C7	1.515 (5)	C17—H17B	0.980
C6—H6	1.000	C17—H17C	0.980
C7—H7A	0.990	O3—H3	0.840
C7—H7B	0.990	O3'—H3'	0.840
N2—Pd1—N4	177.17 (11)	C5—C6—H6	110.4
N2—Pd1—N1	83.80 (12)	N2—C7—C6	108.5 (3)
N4—Pd1—N1	96.36 (12)	N2—C7—H7A	110.0
N2—Pd1—N3	96.33 (12)	C6—C7—H7A	110.0
N4—Pd1—N3	83.80 (12)	N2—C7—H7B	110.0
N1—Pd1—N3	174.09 (12)	C6—C7—H7B	110.0
C3—N1—C2	109.3 (3)	H7A—C7—H7B	108.4
C3—N1—C6	102.9 (3)	C9—C8—H8A	109.5
C2—N1—C6	109.4 (3)	C9—C8—H8B	109.5
C3—N1—Pd1	109.2 (2)	H8A—C8—H8B	109.5
C2—N1—Pd1	115.3 (2)	C9—C8—H8C	109.5
C6—N1—Pd1	110.02 (19)	H8A—C8—H8C	109.5
C2—C1—H1A	109.5	H8B—C8—H8C	109.5
C2—C1—H1B	109.5	N3—C9—C8	113.3 (3)
H1A—C1—H1B	109.5	N3—C9—H9A	108.9
C2—C1—H1C	109.5	C8—C9—H9A	108.9
H1A—C1—H1C	109.5	N3—C9—H9B	108.9
H1B—C1—H1C	109.5	C8—C9—H9B	108.9
C7—N2—Pd1	107.9 (2)	H9A—C9—H9B	107.7
C7—N2—H2A	110.1	N3—C10—C11	105.8 (3)
Pd1—N2—H2A	110.1	N3—C10—H10A	110.6
C7—N2—H2B	110.1	C11—C10—H10A	110.6
Pd1—N2—H2B	110.1	N3—C10—H10B	110.6
H2A—N2—H2B	108.4	C11—C10—H10B	110.6
N1—C2—C1	113.5 (3)	H10A—C10—H10B	108.7
N1—C2—H2C	108.9	C10—C11—C12	105.0 (3)
C1—C2—H2C	108.9	C10—C11—H11A	110.8
N1—C2—H2D	108.9	C12—C11—H11A	110.8
C1—C2—H2D	108.9	C10—C11—H11B	110.8
H2C—C2—H2D	107.7	C12—C11—H11B	110.8
C9—N3—C10	109.4 (3)	H11A—C11—H11B	108.8
C9—N3—C13	110.3 (3)	C11—C12—C13	106.2 (3)
C10—N3—C13	102.5 (3)	C11—C12—H12A	110.5
C9—N3—Pd1	114.4 (2)	C13—C12—H12A	110.5
C10—N3—Pd1	110.0 (2)	C11—C12—H12B	110.5
C13—N3—Pd1	109.6 (2)	C13—C12—H12B	110.5
N1—C3—C4	105.4 (3)	H12A—C12—H12B	108.7
N1—C3—H3A	110.7	C14—C13—N3	108.3 (3)
C4—C3—H3A	110.7	C14—C13—C12	112.8 (3)
N1—C3—H3B	110.7	N3—C13—C12	105.5 (3)
C4—C3—H3B	110.7	C14—C13—H13	110.0
H3A—C3—H3B	108.8	N3—C13—H13	110.0
C14—N4—Pd1	107.8 (2)	C12—C13—H13	110.0
C14—N4—H4A	110.1	N4—C14—C13	108.2 (3)
Pd1—N4—H4A	110.1	N4—C14—H14A	110.1
C14—N4—H4B	110.1	C13—C14—H14A	110.1
Pd1—N4—H4B	110.1	N4—C14—H14B	110.1
H4A—N4—H4B	108.5	C13—C14—H14B	110.1
C5—C4—C3	105.2 (3)	H14A—C14—H14B	108.4
C5—C4—H4C	110.7	O1—C15—H15A	109.5
C3—C4—H4C	110.7	O1—C15—H15B	109.5
C5—C4—H4D	110.7	H15A—C15—H15B	109.5
C3—C4—H4D	110.7	O1—C15—H15C	109.5
H4C—C4—H4D	108.8	H15A—C15—H15C	109.5
C4—C5—C6	105.7 (3)	H15B—C15—H15C	109.5
C4—C5—H5A	110.6	C15—O1—H1	109.5
C6—C5—H5A	110.6	O2—C16—H16A	109.5
C4—C5—H5B	110.6	O2—C16—H16B	109.5
C6—C5—H5B	110.6	H16A—C16—H16B	109.5
H5A—C5—H5B	108.7	O2—C16—H16C	109.5
C7—C6—N1	107.9 (3)	H16A—C16—H16C	109.5
C7—C6—C5	111.8 (3)	H16B—C16—H16C	109.5
N1—C6—C5	105.8 (3)	C16—O2—H2	109.5
C7—C6—H6	110.4	C17—O3—H3	109.5
N1—C6—H6	110.4
N2—Pd1—N1—C3	−107.7 (2)	C3—N1—C6—C5	−33.8 (3)
N4—Pd1—N1—C3	75.1 (2)	C2—N1—C6—C5	82.3 (3)
N2—Pd1—N1—C2	128.8 (2)	Pd1—N1—C6—C5	−150.1 (2)
N4—Pd1—N1—C2	−48.4 (2)	C4—C5—C6—C7	−101.5 (4)
N2—Pd1—N1—C6	4.5 (2)	C4—C5—C6—N1	15.7 (4)
N4—Pd1—N1—C6	−172.6 (2)	Pd1—N2—C7—C6	−45.9 (3)
N1—Pd1—N2—C7	22.7 (2)	N1—C6—C7—N2	50.1 (4)
N3—Pd1—N2—C7	−151.4 (2)	C5—C6—C7—N2	166.0 (3)
C3—N1—C2—C1	−171.5 (3)	C10—N3—C9—C8	−175.0 (3)
C6—N1—C2—C1	76.6 (4)	C13—N3—C9—C8	73.0 (4)
Pd1—N1—C2—C1	−48.0 (4)	Pd1—N3—C9—C8	−51.1 (4)
N2—Pd1—N3—C9	−48.0 (2)	C9—N3—C10—C11	−78.2 (4)
N4—Pd1—N3—C9	129.1 (2)	C13—N3—C10—C11	38.9 (4)
N2—Pd1—N3—C10	75.6 (3)	Pd1—N3—C10—C11	155.4 (3)
N4—Pd1—N3—C10	−107.3 (3)	N3—C10—C11—C12	−27.7 (4)
N2—Pd1—N3—C13	−172.5 (2)	C10—C11—C12—C13	5.4 (4)
N4—Pd1—N3—C13	4.7 (2)	C9—N3—C13—C14	−157.6 (3)
C2—N1—C3—C4	−76.9 (4)	C10—N3—C13—C14	86.0 (3)
C6—N1—C3—C4	39.2 (3)	Pd1—N3—C13—C14	−30.8 (3)
Pd1—N1—C3—C4	156.1 (2)	C9—N3—C13—C12	81.4 (4)
N1—Pd1—N4—C14	−151.3 (2)	C10—N3—C13—C12	−35.0 (4)
N3—Pd1—N4—C14	22.8 (2)	Pd1—N3—C13—C12	−151.8 (2)
N1—C3—C4—C5	−29.6 (4)	C11—C12—C13—C14	−99.7 (4)
C3—C4—C5—C6	8.2 (4)	C11—C12—C13—N3	18.4 (4)
C3—N1—C6—C7	86.0 (3)	Pd1—N4—C14—C13	−46.1 (3)
C2—N1—C6—C7	−157.9 (3)	N3—C13—C14—N4	50.8 (4)
Pd1—N1—C6—C7	−30.3 (3)	C12—C13—C14—N4	167.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl1^i	0.92	2.35	3.225 (3)	159
N2—H2B···O1^ii	0.92	2.07	2.949 (4)	160
N4—H4A···Cl2^iii	0.92	2.37	3.240 (3)	158
N4—H4B···Cl2	0.92	2.36	3.222 (3)	156
O1—H1···Cl1	0.84	2.31	3.127 (3)	166
O2—H2···Cl1	0.84	2.37	3.205 (4)	176
O3—H3···Cl2^iv	0.84	2.40	3.146 (8)	148
O3′—H3′···Cl2^iv	0.84	2.50	3.224 (8)	145

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