Di­bromido­[N-(1-di­ethyl­amino-1-oxo-3-phenyl­propan-2-yl)-N′-(pyridin-2-yl)imidazol-2-yl­idene]palladium(II) di­chloro­methane monosolvate

Liu, Q.; Mao, P.; Yuan, J.; Xiao, Y.; Yang, L.

doi:10.1107/S241431461900899X

Dibromido[N-(1-diethylamino-1-oxo-3-phenylpropan-2-yl)-N′-(pyridin-2-yl)imidazol-2-ylidene]palladium(II) dichloromethane monosolvate

Q. Liu, P. Mao, J. Yuan, Y. Xiao and L. Yang

In the molecule of the title N,N′-disubstituted imidazol-2-ylidene palladium(II) complex, [PdBr₂(C₂₁H₂₄N₄O)]·CH₂Cl₂, the palladium(II) atom adopts a slightly distorted square-planar coordination (r.m.s. deviation = 0.0145 Å), and the five-membered chelate ring is almost planar [maximum displacement = 0.015 (8) Å]. The molecular conformation is enforced by intramolecular C—H

Br hydrogen bonds. In the crystal, complex molecules and dichloromethane molecules are linked into a three-dimensional network by C—H

O and C—H

Br hydrogen bonds.

Keywords: crystal structure; imidazol-2-ylidene; palladium.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S241431461900899X/rz4032sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S241431461900899X/rz4032Isup2.hkl Contains datablock I

CCDC reference: 1935988

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.016 Å
R factor = 0.049
wR factor = 0.138
Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.29 Report
PLAT241_ALERT_2_C High   'MainMol' Ueq as Compared to Neighbors of        C15 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        Pd1 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N4 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C18 Check
PLAT244_ALERT_4_C Low    'Solvent' Ueq as Compared to Neighbors of        C22 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       Cl1      0.187 Check
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.01587 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H9       ..H18A     .       1.98 Ang.
                                                      x,y,z  =      1_555 Check
PLAT741_ALERT_1_C Bond    Calc    1.391(9), Rep     1.39000 ......    Missing s.u.
              C5       -C4              1.555   1.555 ........     #    3 Check
PLAT741_ALERT_1_C Bond    Calc    1.390(8), Rep     1.39000 ......    Missing s.u.
              C5       -N1              1.555   1.555 ........     #    4 Check
PLAT741_ALERT_1_C Bond    Calc   1.390(12), Rep     1.39000 ......    Missing s.u.
              C4       -C3              1.555   1.555 ........     #    7 Check
PLAT741_ALERT_1_C Bond    Calc   1.389(11), Rep     1.39000 ......    Missing s.u.
              C3       -C2              1.555   1.555 ........     #    9 Check
PLAT741_ALERT_1_C Bond    Calc   1.390(11), Rep     1.39000 ......    Missing s.u.
              C2       -C1              1.555   1.555 ........     #   11 Check
PLAT741_ALERT_1_C Bond    Calc    1.391(9), Rep     1.39000 ......    Missing s.u.
              C1       -N1              1.555   1.555 ........     #   13 Check
PLAT741_ALERT_1_C Bond    Calc   1.389(15), Rep     1.39000 ......    Missing s.u.
              C11      -C16             1.555   1.555 ........     #   30 Check
PLAT741_ALERT_1_C Bond    Calc   1.390(12), Rep     1.39000 ......    Missing s.u.
              C11      -C12             1.555   1.555 ........     #   31 Check
PLAT741_ALERT_1_C Bond    Calc   1.391(15), Rep     1.39000 ......    Missing s.u.
              C16      -C15             1.555   1.555 ........     #   33 Check
PLAT741_ALERT_1_C Bond    Calc   1.389(17), Rep     1.39000 ......    Missing s.u.
              C15      -C14             1.555   1.555 ........     #   35 Check
PLAT741_ALERT_1_C Bond    Calc   1.389(18), Rep     1.39000 ......    Missing s.u.
              C14      -C13             1.555   1.555 ........     #   37 Check
PLAT741_ALERT_1_C Bond    Calc   1.390(15), Rep     1.39000 ......    Missing s.u.
              C13      -C12             1.555   1.555 ........     #   39 Check
PLAT742_ALERT_1_C Angle   Calc    120.0(6), Rep      120.00 ......    Missing s.u.
              C4      -C5      -N1         1.555  1.555  1.555     #    1 Check
PLAT742_ALERT_1_C Angle   Calc    120.0(6), Rep      120.00 ......    Missing s.u.
              C3      -C4      -C5         1.555  1.555  1.555     #    5 Check
PLAT742_ALERT_1_C Angle   Calc    120.1(6), Rep      120.00 ......    Missing s.u.
              C4      -C3      -C2         1.555  1.555  1.555     #    8 Check
PLAT742_ALERT_1_C Angle   Calc    120.0(6), Rep      120.00 ......    Missing s.u.
              C1      -C2      -C3         1.555  1.555  1.555     #   11 Check
PLAT742_ALERT_1_C Angle   Calc    120.0(6), Rep      120.00 ......    Missing s.u.
              C2      -C1      -N1         1.555  1.555  1.555     #   14 Check
PLAT742_ALERT_1_C Angle   Calc    120.0(5), Rep      120.00 ......    Missing s.u.
              C1      -N1      -C5         1.555  1.555  1.555     #   17 Check
PLAT742_ALERT_1_C Angle   Calc    120.0(9), Rep      120.00 ......    Missing s.u.
              C16     -C11     -C12        1.555  1.555  1.555     #   41 Check
PLAT742_ALERT_1_C Angle   Calc    120.0(8), Rep      120.00 ......    Missing s.u.
              C15     -C16     -C11        1.555  1.555  1.555     #   44 Check
PLAT742_ALERT_1_C Angle   Calc    120.0(9), Rep      120.00 ......    Missing s.u.
              C16     -C15     -C14        1.555  1.555  1.555     #   47 Check
PLAT742_ALERT_1_C Angle   Calc   120.1(10), Rep      120.00 ......    Missing s.u.
              C13     -C14     -C15        1.555  1.555  1.555     #   50 Check
PLAT742_ALERT_1_C Angle   Calc    120.0(8), Rep      120.00 ......    Missing s.u.
              C12     -C13     -C14        1.555  1.555  1.555     #   53 Check
PLAT742_ALERT_1_C Angle   Calc   120.0(10), Rep      120.00 ......    Missing s.u.
              C13     -C12     -C11        1.555  1.555  1.555     #   56 Check
PLAT743_ALERT_1_C Torsion Calc     0.1(12), Rep        0.00 ......    Missing s.u.
              C4  -C5  -N1  -C1     1.555   1.555   1.555   1.555  #    2 Check
PLAT743_ALERT_1_C Torsion Calc    -0.1(13), Rep        0.00 ......    Missing s.u.
              C2  -C1  -N1  -C5     1.555   1.555   1.555   1.555  #    8 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.597          2 Report
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage         79 %
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density.          0 Info

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT791_ALERT_4_G Model has Chirality at C9          (Chiral SPGR)          S Verify
PLAT794_ALERT_5_G Tentative Bond Valency for Pd1       (II)      .       2.11 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        76% Note

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

  26 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 164
              palladium(II)complex, [PdBr~2~(C~21~H~24~2~N~4~O)]\\cdotCH~2~Cl~2~, the
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   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 top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Dibromido[N-(1-diethylamino-1-oxo-3-phenylpropan-2-yl)-N'-(pyridin-2-yl)imidazol-2-ylidene]palladium(II) dichloromethane monosolvate top

Crystal data top

[PdBr₂(C₂₁H₂₄N₄O)]·CH₂Cl₂	D_x = 1.737 Mg m⁻³
M_r = 699.59	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 2891 reflections
a = 17.6670 (4) Å	θ = 3.8–70.6°
b = 12.8871 (3) Å	µ = 11.11 mm⁻¹
c = 11.7476 (3) Å	T = 293 K
V = 2674.65 (11) Å³	, light yellow
Z = 4	0.33 × 0.17 × 0.07 mm
F(000) = 1376

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	4332 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3852 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 16.2312 pixels mm^-1	θ_max = 67.1°, θ_min = 4.3°
ω scans	h = −10→21
Absorption correction: gaussian (CrysAlis PRO; Agilent, 2014)	k = −15→9
T_min = 0.149, T_max = 0.607	l = −12→14
7177 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.0803P)² + 0.2381P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.138	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 1.01 e Å⁻³
4332 reflections	Δρ_min = −0.44 e Å⁻³
267 parameters	Absolute structure: Flack x determined using 1279 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.009 (13)
Primary atom site location: iterative

Special details top

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.

Refinement. All H atoms were placed geometrically and refined using a riding atom approximation, with C–H = 0.93-0.98 Å, and with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C) for methyl H atoms. A rotating model was used for the methyl groups.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.59851 (6)	0.56133 (8)	0.49147 (12)	0.0705 (3)
Br2	0.60329 (6)	0.82311 (9)	0.4899 (2)	0.0984 (6)
C5	0.3460 (3)	0.6459 (4)	0.4318 (7)	0.072 (3)
C4	0.2814 (3)	0.5863 (7)	0.4143 (9)	0.092 (4)
H4	0.2352	0.6185	0.4005	0.110*
C3	0.2860 (4)	0.4787 (6)	0.4174 (10)	0.099 (5)
H3	0.2428	0.4389	0.4056	0.119*
C2	0.3550 (5)	0.4306 (4)	0.4379 (9)	0.096 (4)
H2	0.3581	0.3586	0.4400	0.115*
C1	0.4196 (4)	0.4901 (5)	0.4554 (8)	0.081 (3)
H1	0.4658	0.4580	0.4692	0.098*
N1	0.4151 (3)	0.5978 (5)	0.4524 (6)	0.064 (2)
C6	0.4184 (5)	0.7990 (9)	0.4476 (8)	0.060 (2)
C7	0.2929 (7)	0.8202 (11)	0.4163 (13)	0.086 (4)
H7	0.2423	0.8042	0.4026	0.104*
C8	0.3227 (7)	0.9141 (11)	0.4248 (13)	0.083 (4)
H8	0.2966	0.9766	0.4203	0.100*
C9	0.4565 (7)	0.9878 (8)	0.4515 (9)	0.061 (2)
H9	0.5008	0.9641	0.4944	0.074*
C10	0.4826 (9)	1.0268 (10)	0.3327 (10)	0.081 (4)
H10A	0.5024	0.9687	0.2892	0.097*
H10B	0.4394	1.0546	0.2918	0.097*
C11	0.5431 (6)	1.1098 (6)	0.3424 (8)	0.083 (4)
C16	0.6182 (6)	1.0813 (6)	0.3583 (10)	0.104 (5)
H16	0.6317	1.0116	0.3589	0.125*
C15	0.6733 (5)	1.1572 (10)	0.3732 (12)	0.145 (9)
H15	0.7236	1.1381	0.3838	0.174*
C14	0.6532 (7)	1.2614 (9)	0.3722 (11)	0.124 (7)
H14	0.6901	1.3122	0.3822	0.149*
C13	0.5781 (8)	1.2899 (5)	0.3563 (9)	0.114 (6)
H13	0.5647	1.3597	0.3556	0.137*
C12	0.5230 (6)	1.2141 (7)	0.3414 (8)	0.096 (5)
H12	0.4727	1.2331	0.3307	0.116*
C17	0.4186 (7)	1.0784 (8)	0.5167 (11)	0.069 (3)
C18	0.4815 (7)	1.0208 (10)	0.6941 (9)	0.074 (3)
H18A	0.4820	0.9524	0.6597	0.089*
H18B	0.4592	1.0140	0.7692	0.089*
C19	0.5616 (10)	1.0567 (14)	0.7076 (17)	0.118 (6)
H19A	0.5861	1.0570	0.6346	0.177*
H19B	0.5881	1.0105	0.7579	0.177*
H19C	0.5621	1.1255	0.7388	0.177*
C20	0.3960 (13)	1.1763 (13)	0.6898 (12)	0.120 (7)
H20A	0.3452	1.1870	0.6607	0.144*
H20B	0.3921	1.1579	0.7696	0.144*
C21	0.4391 (16)	1.2722 (13)	0.679 (2)	0.179 (13)
H21A	0.4528	1.2822	0.6003	0.269*
H21B	0.4840	1.2679	0.7242	0.269*
H21C	0.4087	1.3295	0.7038	0.269*
N2	0.3517 (5)	0.7504 (7)	0.4316 (8)	0.066 (2)
N3	0.4022 (5)	0.9018 (7)	0.4421 (8)	0.065 (2)
N4	0.4331 (6)	1.0885 (8)	0.6254 (8)	0.072 (3)
O1	0.3743 (6)	1.1351 (7)	0.4652 (7)	0.090 (3)
Pd1	0.50333 (3)	0.70009 (5)	0.46982 (5)	0.0533 (2)
C22	0.7655 (10)	0.3250 (16)	0.7695 (17)	0.121 (6)
H22A	0.8019	0.3344	0.8304	0.146*
H22B	0.7934	0.3225	0.6984	0.146*
Cl1	0.7074 (5)	0.4286 (8)	0.7666 (10)	0.253 (6)
Cl2	0.7195 (5)	0.2046 (6)	0.7892 (5)	0.186 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0626 (6)	0.0614 (6)	0.0876 (8)	0.0079 (4)	−0.0037 (6)	−0.0007 (5)
Br2	0.0518 (5)	0.0620 (6)	0.1813 (18)	−0.0015 (4)	−0.0171 (9)	0.0036 (9)
C5	0.039 (4)	0.099 (8)	0.076 (7)	0.001 (5)	0.012 (5)	−0.017 (6)
C4	0.058 (6)	0.111 (10)	0.107 (10)	−0.012 (6)	0.011 (7)	−0.037 (9)
C3	0.072 (7)	0.100 (10)	0.124 (12)	−0.028 (7)	0.009 (9)	−0.022 (9)
C2	0.085 (8)	0.087 (9)	0.115 (11)	−0.017 (7)	0.009 (9)	−0.012 (8)
C1	0.077 (7)	0.066 (7)	0.101 (9)	−0.010 (5)	−0.001 (7)	0.002 (6)
N1	0.047 (4)	0.079 (5)	0.066 (5)	−0.002 (4)	0.004 (4)	−0.013 (5)
C6	0.053 (4)	0.065 (6)	0.061 (5)	0.014 (4)	−0.001 (4)	−0.013 (5)
C7	0.055 (5)	0.095 (9)	0.109 (9)	0.013 (6)	−0.015 (7)	−0.024 (8)
C8	0.061 (6)	0.093 (9)	0.096 (9)	0.017 (6)	−0.007 (6)	−0.011 (7)
C9	0.072 (6)	0.056 (5)	0.057 (5)	0.011 (4)	−0.003 (5)	−0.001 (4)
C10	0.105 (10)	0.076 (7)	0.062 (6)	0.004 (7)	−0.001 (7)	0.000 (5)
C11	0.123 (11)	0.072 (7)	0.053 (5)	0.011 (7)	0.007 (7)	0.009 (5)
C16	0.100 (10)	0.094 (10)	0.117 (12)	0.003 (9)	0.023 (10)	0.035 (9)
C15	0.127 (16)	0.125 (15)	0.18 (2)	−0.003 (13)	0.004 (17)	0.065 (15)
C14	0.153 (18)	0.108 (14)	0.112 (13)	−0.026 (13)	0.022 (14)	0.012 (10)
C13	0.173 (19)	0.064 (8)	0.105 (11)	−0.010 (11)	0.020 (12)	0.005 (7)
C12	0.136 (13)	0.070 (8)	0.083 (7)	0.022 (8)	0.022 (8)	0.013 (6)
C17	0.069 (6)	0.065 (6)	0.073 (6)	0.011 (5)	0.005 (6)	−0.001 (5)
C18	0.079 (8)	0.088 (8)	0.055 (5)	0.015 (6)	−0.005 (5)	−0.005 (5)
C19	0.102 (12)	0.119 (13)	0.133 (15)	−0.005 (10)	−0.035 (12)	−0.031 (11)
C20	0.180 (19)	0.106 (12)	0.074 (8)	0.056 (13)	−0.009 (11)	−0.024 (8)
C21	0.30 (4)	0.072 (11)	0.17 (2)	0.039 (15)	−0.06 (2)	−0.043 (12)
N2	0.048 (4)	0.078 (6)	0.072 (5)	0.002 (4)	0.003 (4)	−0.011 (5)
N3	0.059 (4)	0.071 (5)	0.064 (5)	0.009 (4)	−0.001 (4)	−0.005 (4)
N4	0.082 (6)	0.073 (6)	0.061 (5)	0.016 (5)	−0.009 (5)	−0.015 (4)
O1	0.111 (7)	0.086 (5)	0.072 (5)	0.047 (5)	−0.018 (5)	−0.008 (4)
Pd1	0.0455 (3)	0.0578 (4)	0.0565 (3)	0.0016 (3)	0.0020 (3)	−0.0010 (3)
C22	0.089 (9)	0.174 (18)	0.101 (11)	−0.006 (11)	0.012 (9)	0.031 (12)
Cl1	0.186 (7)	0.284 (10)	0.290 (11)	0.124 (7)	0.111 (8)	0.154 (9)
Cl2	0.210 (7)	0.217 (7)	0.130 (4)	−0.105 (7)	0.024 (5)	−0.039 (4)

Geometric parameters (Å, º) top

Br1—Pd1	2.4678 (12)	C11—C12	1.3900
Br2—Pd1	2.3849 (12)	C16—H16	0.9300
C5—C4	1.3900	C16—C15	1.3900
C5—N1	1.3900	C15—H15	0.9300
C5—N2	1.350 (11)	C15—C14	1.3900
C4—H4	0.9300	C14—H14	0.9300
C4—C3	1.3900	C14—C13	1.3900
C3—H3	0.9300	C13—H13	0.9300
C3—C2	1.3900	C13—C12	1.3900
C2—H2	0.9300	C12—H12	0.9300
C2—C1	1.3900	C17—N4	1.309 (16)
C1—H1	0.9300	C17—O1	1.229 (14)
C1—N1	1.3900	C18—H18A	0.9700
N1—Pd1	2.052 (5)	C18—H18B	0.9700
C6—N2	1.347 (13)	C18—C19	1.497 (19)
C6—N3	1.357 (14)	C18—N4	1.464 (15)
C6—Pd1	1.986 (9)	C19—H19A	0.9600
C7—H7	0.9300	C19—H19B	0.9600
C7—C8	1.323 (19)	C19—H19C	0.9600
C7—N2	1.387 (14)	C20—H20A	0.9700
C8—H8	0.9300	C20—H20B	0.9700
C8—N3	1.429 (14)	C20—C21	1.46 (3)
C9—H9	0.9800	C20—N4	1.511 (16)
C9—C10	1.554 (16)	C21—H21A	0.9600
C9—C17	1.549 (14)	C21—H21B	0.9600
C9—N3	1.469 (14)	C21—H21C	0.9600
C10—H10A	0.9700	C22—H22A	0.9700
C10—H10B	0.9700	C22—H22B	0.9700
C10—C11	1.516 (16)	C22—Cl1	1.684 (19)
C11—C16	1.3900	C22—Cl2	1.766 (19)

C4—C5—N1	120.0	C12—C13—H13	120.0
N2—C5—C4	127.7 (6)	C11—C12—H12	120.0
N2—C5—N1	112.3 (6)	C13—C12—C11	120.0
C5—C4—H4	120.0	C13—C12—H12	120.0
C3—C4—C5	120.0	N4—C17—C9	118.2 (10)
C3—C4—H4	120.0	O1—C17—C9	118.6 (11)
C4—C3—H3	120.0	O1—C17—N4	123.2 (11)
C4—C3—C2	120.0	H18A—C18—H18B	107.5
C2—C3—H3	120.0	C19—C18—H18A	108.5
C3—C2—H2	120.0	C19—C18—H18B	108.5
C1—C2—C3	120.0	N4—C18—H18A	108.5
C1—C2—H2	120.0	N4—C18—H18B	108.5
C2—C1—H1	120.0	N4—C18—C19	115.2 (13)
C2—C1—N1	120.0	C18—C19—H19A	109.5
N1—C1—H1	120.0	C18—C19—H19B	109.5
C5—N1—Pd1	113.4 (4)	C18—C19—H19C	109.5
C1—N1—C5	120.0	H19A—C19—H19B	109.5
C1—N1—Pd1	126.5 (4)	H19A—C19—H19C	109.5
N2—C6—N3	105.3 (9)	H19B—C19—H19C	109.5
N2—C6—Pd1	112.4 (8)	H20A—C20—H20B	108.0
N3—C6—Pd1	142.3 (8)	C21—C20—H20A	109.4
C8—C7—H7	126.7	C21—C20—H20B	109.4
C8—C7—N2	106.6 (11)	C21—C20—N4	111.3 (17)
N2—C7—H7	126.7	N4—C20—H20A	109.4
C7—C8—H8	126.2	N4—C20—H20B	109.4
C7—C8—N3	107.5 (11)	C20—C21—H21A	109.5
N3—C8—H8	126.2	C20—C21—H21B	109.5
C10—C9—H9	109.0	C20—C21—H21C	109.5
C17—C9—H9	109.0	H21A—C21—H21B	109.5
C17—C9—C10	109.2 (9)	H21A—C21—H21C	109.5
N3—C9—H9	109.0	H21B—C21—H21C	109.5
N3—C9—C10	111.7 (9)	C5—N2—C7	126.3 (9)
N3—C9—C17	108.9 (9)	C6—N2—C5	121.9 (9)
C9—C10—H10A	109.3	C6—N2—C7	111.8 (9)
C9—C10—H10B	109.3	C6—N3—C8	108.7 (10)
H10A—C10—H10B	107.9	C6—N3—C9	126.6 (9)
C11—C10—C9	111.7 (9)	C8—N3—C9	124.7 (10)
C11—C10—H10A	109.3	C17—N4—C18	126.4 (10)
C11—C10—H10B	109.3	C17—N4—C20	118.5 (11)
C16—C11—C10	119.8 (8)	C18—N4—C20	115.1 (10)
C16—C11—C12	120.0	Br2—Pd1—Br1	88.10 (4)
C12—C11—C10	120.1 (8)	N1—Pd1—Br1	93.58 (18)
C11—C16—H16	120.0	N1—Pd1—Br2	178.31 (18)
C15—C16—C11	120.0	C6—Pd1—Br1	173.4 (3)
C15—C16—H16	120.0	C6—Pd1—Br2	98.4 (3)
C16—C15—H15	120.0	C6—Pd1—N1	79.9 (4)
C16—C15—C14	120.0	H22A—C22—H22B	107.5
C14—C15—H15	120.0	Cl1—C22—H22A	108.6
C15—C14—H14	120.0	Cl1—C22—H22B	108.6
C13—C14—C15	120.0	Cl1—C22—Cl2	114.8 (10)
C13—C14—H14	120.0	Cl2—C22—H22A	108.6
C14—C13—H13	120.0	Cl2—C22—H22B	108.6
C12—C13—C14	120.0

C5—C4—C3—C2	0.0	C16—C15—C14—C13	0.0
C4—C5—N1—C1	0.0	C15—C14—C13—C12	0.0
C4—C5—N1—Pd1	177.8 (5)	C14—C13—C12—C11	0.0
C4—C5—N2—C6	−178.7 (8)	C12—C11—C16—C15	0.0
C4—C5—N2—C7	1.6 (16)	C17—C9—C10—C11	63.9 (13)
C4—C3—C2—C1	0.0	C17—C9—N3—C6	−143.5 (10)
C3—C2—C1—N1	0.0	C17—C9—N3—C8	36.9 (15)
C2—C1—N1—C5	0.0	C19—C18—N4—C17	95.2 (16)
C2—C1—N1—Pd1	−177.5 (6)	C19—C18—N4—C20	−86.2 (17)
N1—C5—C4—C3	0.0	C21—C20—N4—C17	−85 (2)
N1—C5—N2—C6	1.3 (13)	C21—C20—N4—C18	96.5 (16)
N1—C5—N2—C7	−178.4 (11)	N2—C5—C4—C3	179.9 (9)
C7—C8—N3—C6	−2.1 (16)	N2—C5—N1—C1	−180.0 (8)
C7—C8—N3—C9	177.6 (11)	N2—C5—N1—Pd1	−2.1 (8)
C8—C7—N2—C5	178.6 (11)	N2—C6—N3—C8	1.4 (13)
C8—C7—N2—C6	−1.1 (16)	N2—C6—N3—C9	−178.3 (9)
C9—C10—C11—C16	82.4 (12)	N2—C7—C8—N3	1.9 (16)
C9—C10—C11—C12	−94.2 (11)	N3—C6—N2—C5	−179.9 (9)
C9—C17—N4—C18	−1.1 (19)	N3—C6—N2—C7	−0.2 (13)
C9—C17—N4—C20	−179.7 (13)	N3—C9—C10—C11	−175.6 (9)
C10—C9—C17—N4	−139.3 (12)	N3—C9—C17—N4	98.5 (12)
C10—C9—C17—O1	43.3 (15)	N3—C9—C17—O1	−79.0 (13)
C10—C9—N3—C6	95.8 (12)	O1—C17—N4—C18	176.2 (12)
C10—C9—N3—C8	−83.8 (14)	O1—C17—N4—C20	−2 (2)
C10—C11—C16—C15	−176.6 (9)	Pd1—C6—N2—C5	0.3 (13)
C10—C11—C12—C13	176.6 (9)	Pd1—C6—N2—C7	180.0 (9)
C11—C16—C15—C14	0.0	Pd1—C6—N3—C8	−178.9 (10)
C16—C11—C12—C13	0.0	Pd1—C6—N3—C9	1.4 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Br2ⁱ	0.93	2.77	3.540 (7)	141
C9—H9···Br2	0.98	2.57	3.381 (12)	141
C16—H16···Br2	0.93	2.92	3.678 (9)	140
C22—H22A···Br1ⁱⁱ	0.97	2.91	3.836 (19)	160
C22—H22B···O1ⁱⁱⁱ	0.97	2.46	3.40 (2)	164

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

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Di­bromido­[N-(1-di­ethyl­amino-1-oxo-3-phenyl­propan-2-yl)-N′-(pyridin-2-yl)imidazol-2-yl­idene]palladium(II) di­chloro­methane monosolvate

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Key indicators

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Dibromido[N-(1-diethylamino-1-oxo-3-phenylpropan-2-yl)-N′-(pyridin-2-yl)imidazol-2-ylidene]palladium(II) dichloromethane monosolvate