The structure of the title compound, [PdBr
2(C
23H
24N
4O
2)], was determined at 273 K. It crystallizes in the non-centrosymmetric trigonal space group
P3
2. Non-classical hydrogen bonds of types C—H
Br and C—H
O exist in the structure.
Supporting information
CCDC reference: 251599
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.014 Å
- R factor = 0.052
- wR factor = 0.113
- Data-to-parameter ratio = 20.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT213_ALERT_2_B Atom C2 has ADP max/min Ratio ............. 4.70 oblate
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.20 Ratio
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.66 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.33 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors for O1
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14
PLAT732_ALERT_1_C Angle Calc 92.84(3), Rep 92.84(12) ...... 4.00 su-Rat
BR1 -PD1 -BR2 1.555 1.555 1.555
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 28.36
From the CIF: _reflns_number_total 5870
Count of symmetry unique reflns 2956
Completeness (_total/calc) 198.58%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 2914
Fraction of Friedel pairs measured 0.986
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
5 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
4 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
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Dibromo[2,2',3,3'-tetrahydro-3,3'-bis(4-methoxylbenzyl)-1,1'-methylenedi-
1
H-imidazole-
κ2C2,
C2']palladium(II)
top
Crystal data top
[PdBr2(C23H24N4O2)] | Dx = 1.840 Mg m−3 |
Mr = 654.68 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, P32 | Cell parameters from 3022 reflections |
Hall symbol: P 32 | θ = 2.6–28.8° |
a = 15.41 (3) Å | µ = 4.20 mm−1 |
c = 8.617 (12) Å | T = 273 K |
V = 1772 (5) Å3 | Prism, colorless |
Z = 3 | 0.23 × 0.20 × 0.19 mm |
F(000) = 966 | |
Data collection top
Bruker SMART 1000 diffractometer | 5870 independent reflections |
Radiation source: fine-focus sealed tube | 4809 reflections with I > 2σ |
Graphite monochromator | Rint = 0.064 |
ω scans | θmax = 28.4°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −20→20 |
Tmin = 0.401, Tmax = 0.453 | k = −14→20 |
13263 measured reflections | l = −11→11 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0373P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.002 |
5870 reflections | Δρmax = 1.19 e Å−3 |
283 parameters | Δρmin = −1.49 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2914 Friedel pairs [CHECK] |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.029 (11) |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | −0.00794 (6) | 0.46493 (6) | 0.06749 (8) | 0.01902 (16) | |
Br2 | 0.22881 (6) | 0.48733 (6) | −0.02795 (8) | 0.02409 (19) | |
N1 | −0.0466 (5) | 0.3512 (5) | 0.4448 (7) | 0.0183 (13) | |
N2 | 0.0922 (5) | 0.4707 (5) | 0.5338 (7) | 0.0189 (14) | |
N3 | 0.2486 (4) | 0.4903 (5) | 0.4767 (7) | 0.0157 (12) | |
N4 | 0.2671 (5) | 0.3862 (5) | 0.3371 (6) | 0.0161 (13) | |
O1 | −0.1127 (6) | −0.0871 (6) | 0.3691 (11) | 0.063 (2) | |
O2 | 0.5966 (4) | 0.2918 (4) | 0.1048 (6) | 0.0234 (12) | |
Pd1 | 0.12109 (4) | 0.44651 (4) | 0.20684 (5) | 0.01489 (12) | |
C1 | 0.0463 (5) | 0.4184 (5) | 0.4009 (7) | 0.0119 (14) | |
C2 | −0.0586 (7) | 0.3584 (7) | 0.6028 (8) | 0.0281 (19) | |
H2A | −0.1162 | 0.3182 | 0.6601 | 0.034* | |
C3 | 0.0267 (6) | 0.4328 (6) | 0.6574 (8) | 0.0220 (17) | |
H3A | 0.0399 | 0.4552 | 0.7595 | 0.026* | |
C4 | 0.1967 (6) | 0.5417 (6) | 0.5383 (8) | 0.0172 (16) | |
H4A | 0.2180 | 0.5639 | 0.6439 | 0.021* | |
H4B | 0.2117 | 0.5997 | 0.4751 | 0.021* | |
C5 | 0.2198 (6) | 0.4381 (6) | 0.3416 (8) | 0.0175 (15) | |
C6 | 0.3119 (6) | 0.4687 (6) | 0.5565 (9) | 0.0222 (17) | |
H6A | 0.3405 | 0.4938 | 0.6530 | 0.027* | |
C7 | 0.3252 (6) | 0.4041 (7) | 0.4687 (10) | 0.0284 (19) | |
H7A | 0.3655 | 0.3767 | 0.4918 | 0.034* | |
C8 | −0.1226 (6) | 0.2731 (6) | 0.3451 (9) | 0.0238 (17) | |
H8A | −0.1112 | 0.2968 | 0.2387 | 0.029* | |
H8B | −0.1882 | 0.2611 | 0.3758 | 0.029* | |
C9 | −0.1218 (7) | 0.1770 (6) | 0.3524 (9) | 0.0280 (19) | |
C10 | −0.1985 (7) | 0.0946 (7) | 0.4182 (9) | 0.032 (2) | |
H10A | −0.2520 | 0.0990 | 0.4591 | 0.038* | |
C11 | −0.2005 (8) | 0.0029 (7) | 0.4272 (11) | 0.039 (2) | |
H11A | −0.2536 | −0.0524 | 0.4746 | 0.047* | |
C12 | −0.1220 (9) | −0.0027 (8) | 0.3641 (13) | 0.043 (2) | |
C13 | −0.0442 (8) | 0.0800 (8) | 0.2922 (14) | 0.050 (3) | |
H13A | 0.0085 | 0.0757 | 0.2475 | 0.060* | |
C14 | −0.0455 (7) | 0.1685 (7) | 0.2876 (12) | 0.038 (2) | |
H14A | 0.0069 | 0.2239 | 0.2393 | 0.046* | |
C15 | −0.1918 (8) | −0.1744 (8) | 0.4152 (15) | 0.0470 (19) | |
H15A | −0.1744 | −0.2261 | 0.4127 | 0.070* | |
H15B | −0.2473 | −0.1918 | 0.3467 | 0.070* | |
H15C | −0.2101 | −0.1675 | 0.5190 | 0.070* | |
C16 | 0.2477 (6) | 0.3091 (6) | 0.2253 (9) | 0.0223 (17) | |
H16A | 0.2237 | 0.3233 | 0.1299 | 0.027* | |
H16B | 0.1951 | 0.2454 | 0.2646 | 0.027* | |
C17 | 0.3393 (6) | 0.3004 (6) | 0.1895 (8) | 0.0185 (16) | |
C18 | 0.3527 (6) | 0.2292 (6) | 0.2648 (9) | 0.0201 (16) | |
H18A | 0.3043 | 0.1849 | 0.3338 | 0.024* | |
C19 | 0.4382 (6) | 0.2236 (6) | 0.2376 (8) | 0.0203 (16) | |
H19A | 0.4467 | 0.1748 | 0.2872 | 0.024* | |
C20 | 0.5102 (6) | 0.2891 (6) | 0.1386 (8) | 0.0178 (16) | |
C21 | 0.4935 (6) | 0.3587 (6) | 0.0588 (8) | 0.0215 (17) | |
H21A | 0.5401 | 0.4017 | −0.0132 | 0.026* | |
C22 | 0.4088 (6) | 0.3633 (6) | 0.0870 (8) | 0.0197 (16) | |
H22A | 0.3986 | 0.4103 | 0.0349 | 0.024* | |
C23 | 0.6212 (8) | 0.2274 (8) | 0.1914 (14) | 0.0470 (19) | |
H23A | 0.6844 | 0.2366 | 0.1563 | 0.070* | |
H23B | 0.5701 | 0.1589 | 0.1761 | 0.070* | |
H23C | 0.6257 | 0.2437 | 0.2997 | 0.070* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0210 (4) | 0.0267 (4) | 0.0102 (3) | 0.0125 (4) | 0.0011 (3) | 0.0027 (3) |
Br2 | 0.0229 (4) | 0.0414 (5) | 0.0092 (3) | 0.0170 (4) | 0.0027 (3) | 0.0017 (3) |
N1 | 0.026 (4) | 0.019 (3) | 0.009 (3) | 0.011 (3) | 0.003 (3) | 0.000 (2) |
N2 | 0.024 (4) | 0.024 (4) | 0.009 (3) | 0.012 (3) | 0.002 (2) | −0.004 (2) |
N3 | 0.022 (3) | 0.019 (3) | 0.006 (2) | 0.010 (3) | −0.001 (2) | −0.001 (2) |
N4 | 0.018 (3) | 0.025 (3) | 0.006 (2) | 0.011 (3) | −0.002 (2) | −0.002 (2) |
O1 | 0.064 (6) | 0.033 (4) | 0.096 (7) | 0.027 (4) | −0.008 (5) | −0.011 (4) |
O2 | 0.025 (3) | 0.028 (3) | 0.019 (3) | 0.014 (3) | 0.007 (2) | 0.009 (2) |
Pd1 | 0.0180 (3) | 0.0210 (3) | 0.0063 (2) | 0.0102 (3) | 0.0006 (2) | −0.0002 (2) |
C1 | 0.017 (4) | 0.012 (3) | 0.009 (3) | 0.009 (3) | −0.003 (3) | −0.003 (3) |
C2 | 0.039 (5) | 0.048 (6) | 0.006 (3) | 0.028 (5) | 0.010 (3) | 0.002 (3) |
C3 | 0.025 (4) | 0.031 (5) | 0.011 (3) | 0.014 (4) | 0.005 (3) | −0.005 (3) |
C4 | 0.026 (4) | 0.018 (4) | 0.008 (3) | 0.011 (3) | −0.001 (3) | −0.005 (3) |
C5 | 0.020 (4) | 0.023 (4) | 0.015 (3) | 0.016 (3) | 0.007 (3) | 0.007 (3) |
C6 | 0.025 (4) | 0.027 (4) | 0.010 (3) | 0.010 (4) | 0.000 (3) | 0.000 (3) |
C7 | 0.026 (5) | 0.042 (5) | 0.021 (4) | 0.020 (4) | −0.005 (3) | −0.002 (4) |
C8 | 0.029 (5) | 0.019 (4) | 0.020 (4) | 0.010 (4) | 0.001 (3) | 0.000 (3) |
C9 | 0.034 (5) | 0.026 (5) | 0.022 (4) | 0.013 (4) | −0.007 (4) | 0.003 (3) |
C10 | 0.039 (5) | 0.042 (5) | 0.013 (3) | 0.020 (5) | 0.003 (4) | −0.002 (3) |
C11 | 0.040 (6) | 0.028 (5) | 0.035 (5) | 0.006 (5) | 0.003 (4) | 0.010 (4) |
C12 | 0.048 (6) | 0.028 (5) | 0.056 (6) | 0.021 (5) | −0.009 (5) | −0.012 (5) |
C13 | 0.041 (6) | 0.039 (6) | 0.070 (8) | 0.021 (5) | 0.002 (6) | −0.016 (6) |
C14 | 0.027 (5) | 0.024 (5) | 0.054 (6) | 0.005 (4) | 0.004 (4) | −0.004 (4) |
C15 | 0.044 (4) | 0.030 (4) | 0.067 (5) | 0.018 (3) | −0.006 (4) | −0.003 (4) |
C16 | 0.029 (4) | 0.026 (4) | 0.017 (4) | 0.017 (4) | −0.002 (3) | −0.001 (3) |
C17 | 0.019 (4) | 0.020 (4) | 0.015 (3) | 0.009 (3) | −0.001 (3) | −0.011 (3) |
C18 | 0.019 (4) | 0.020 (4) | 0.020 (4) | 0.009 (3) | 0.003 (3) | −0.004 (3) |
C19 | 0.028 (4) | 0.023 (4) | 0.015 (3) | 0.017 (4) | 0.002 (3) | 0.001 (3) |
C20 | 0.020 (4) | 0.020 (4) | 0.010 (3) | 0.007 (3) | 0.002 (3) | 0.000 (3) |
C21 | 0.025 (4) | 0.022 (4) | 0.013 (3) | 0.008 (3) | 0.006 (3) | 0.003 (3) |
C22 | 0.032 (4) | 0.018 (4) | 0.010 (3) | 0.013 (4) | −0.007 (3) | −0.002 (3) |
C23 | 0.044 (4) | 0.030 (4) | 0.067 (5) | 0.018 (3) | −0.006 (4) | −0.003 (4) |
Geometric parameters (Å, º) top
Br1—Pd1 | 2.458 (4) | C8—H8B | 0.9700 |
Br2—Pd1 | 2.490 (3) | C9—C10 | 1.353 (12) |
N1—C1 | 1.335 (10) | C9—C14 | 1.367 (13) |
N1—C2 | 1.386 (9) | C10—C11 | 1.400 (13) |
N1—C8 | 1.466 (10) | C10—H10A | 0.9300 |
N2—C1 | 1.374 (9) | C11—C12 | 1.368 (15) |
N2—C3 | 1.380 (9) | C11—H11A | 0.9300 |
N2—C4 | 1.425 (10) | C12—C13 | 1.385 (15) |
N3—C5 | 1.357 (10) | C13—C14 | 1.374 (14) |
N3—C6 | 1.364 (10) | C13—H13A | 0.9300 |
N3—C4 | 1.478 (10) | C14—H14A | 0.9300 |
N4—C5 | 1.325 (10) | C15—H15A | 0.9600 |
N4—C7 | 1.385 (10) | C15—H15B | 0.9600 |
N4—C16 | 1.441 (10) | C15—H15C | 0.9600 |
O1—C15 | 1.347 (13) | C16—C17 | 1.516 (11) |
O1—C12 | 1.379 (12) | C16—H16A | 0.9700 |
O2—C20 | 1.344 (9) | C16—H16B | 0.9700 |
O2—C23 | 1.436 (12) | C17—C22 | 1.352 (11) |
Pd1—C1 | 1.953 (7) | C17—C18 | 1.376 (11) |
Pd1—C5 | 1.969 (8) | C18—C19 | 1.383 (11) |
C2—C3 | 1.326 (12) | C18—H18A | 0.9300 |
C2—H2A | 0.9300 | C19—C20 | 1.362 (11) |
C3—H3A | 0.9300 | C19—H19A | 0.9300 |
C4—H4A | 0.9700 | C20—C21 | 1.402 (11) |
C4—H4B | 0.9700 | C21—C22 | 1.363 (11) |
C6—C7 | 1.346 (12) | C21—H21A | 0.9300 |
C6—H6A | 0.9300 | C22—H22A | 0.9300 |
C7—H7A | 0.9300 | C23—H23A | 0.9600 |
C8—C9 | 1.487 (12) | C23—H23B | 0.9600 |
C8—H8A | 0.9700 | C23—H23C | 0.9600 |
| | | |
C1—N1—C2 | 110.5 (7) | C14—C9—C8 | 120.9 (8) |
C1—N1—C8 | 125.3 (6) | C9—C10—C11 | 122.6 (9) |
C2—N1—C8 | 123.9 (7) | C9—C10—H10A | 118.7 |
C1—N2—C3 | 110.0 (6) | C11—C10—H10A | 118.7 |
C1—N2—C4 | 121.7 (6) | C12—C11—C10 | 117.9 (9) |
C3—N2—C4 | 127.6 (6) | C12—C11—H11A | 121.0 |
C5—N3—C6 | 110.5 (6) | C10—C11—H11A | 121.0 |
C5—N3—C4 | 121.4 (6) | C11—C12—O1 | 124.1 (10) |
C6—N3—C4 | 126.5 (6) | C11—C12—C13 | 120.4 (9) |
C5—N4—C7 | 110.7 (6) | O1—C12—C13 | 115.6 (10) |
C5—N4—C16 | 124.6 (6) | C14—C13—C12 | 119.4 (10) |
C7—N4—C16 | 123.9 (7) | C14—C13—H13A | 120.3 |
C15—O1—C12 | 118.8 (9) | C12—C13—H13A | 120.3 |
C20—O2—C23 | 117.8 (7) | C9—C14—C13 | 121.6 (9) |
C1—Pd1—C5 | 82.5 (3) | C9—C14—H14A | 119.2 |
C1—Pd1—Br1 | 91.3 (2) | C13—C14—H14A | 119.2 |
C5—Pd1—Br1 | 172.8 (2) | O1—C15—H15A | 109.5 |
C1—Pd1—Br2 | 175.4 (2) | O1—C15—H15B | 109.5 |
C5—Pd1—Br2 | 93.3 (2) | H15A—C15—H15B | 109.5 |
Br1—Pd1—Br2 | 92.84 (12) | O1—C15—H15C | 109.5 |
N1—C1—N2 | 104.9 (6) | H15A—C15—H15C | 109.5 |
N1—C1—Pd1 | 134.4 (5) | H15B—C15—H15C | 109.5 |
N2—C1—Pd1 | 120.6 (5) | N4—C16—C17 | 113.0 (6) |
C3—C2—N1 | 107.6 (7) | N4—C16—H16A | 109.0 |
C3—C2—H2A | 126.2 | C17—C16—H16A | 109.0 |
N1—C2—H2A | 126.2 | N4—C16—H16B | 109.0 |
C2—C3—N2 | 106.9 (6) | C17—C16—H16B | 109.0 |
C2—C3—H3A | 126.5 | H16A—C16—H16B | 107.8 |
N2—C3—H3A | 126.5 | C22—C17—C18 | 120.0 (7) |
N2—C4—N3 | 106.6 (6) | C22—C17—C16 | 120.5 (7) |
N2—C4—H4A | 110.4 | C18—C17—C16 | 119.5 (7) |
N3—C4—H4A | 110.4 | C17—C18—C19 | 119.7 (7) |
N2—C4—H4B | 110.4 | C17—C18—H18A | 120.1 |
N3—C4—H4B | 110.4 | C19—C18—H18A | 120.1 |
H4A—C4—H4B | 108.6 | C20—C19—C18 | 120.6 (7) |
N4—C5—N3 | 105.5 (6) | C20—C19—H19A | 119.7 |
N4—C5—Pd1 | 134.3 (6) | C18—C19—H19A | 119.7 |
N3—C5—Pd1 | 120.1 (5) | O2—C20—C19 | 125.8 (7) |
C7—C6—N3 | 106.8 (7) | O2—C20—C21 | 115.4 (6) |
C7—C6—H6A | 126.6 | C19—C20—C21 | 118.7 (7) |
N3—C6—H6A | 126.6 | C22—C21—C20 | 119.9 (7) |
C6—C7—N4 | 106.5 (7) | C22—C21—H21A | 120.0 |
C6—C7—H7A | 126.7 | C20—C21—H21A | 120.0 |
N4—C7—H7A | 126.7 | C17—C22—C21 | 120.9 (7) |
N1—C8—C9 | 113.1 (7) | C17—C22—H22A | 119.5 |
N1—C8—H8A | 109.0 | C21—C22—H22A | 119.5 |
C9—C8—H8A | 109.0 | O2—C23—H23A | 109.5 |
N1—C8—H8B | 109.0 | O2—C23—H23B | 109.5 |
C9—C8—H8B | 109.0 | H23A—C23—H23B | 109.5 |
H8A—C8—H8B | 107.8 | O2—C23—H23C | 109.5 |
C10—C9—C14 | 118.1 (9) | H23A—C23—H23C | 109.5 |
C10—C9—C8 | 120.9 (8) | H23B—C23—H23C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···Br1i | 0.93 | 2.78 | 3.645 (9) | 155 |
C4—H4B···Br2ii | 0.97 | 2.78 | 3.751 (9) | 177 |
C23—H23B···Br1iii | 0.96 | 2.81 | 3.491 (12) | 128 |
C23—H23C···O2iv | 0.96 | 2.45 | 3.175 (13) | 133 |
Symmetry codes: (i) x, y, z+1; (ii) −x+y, −x+1, z+1/3; (iii) −x+y, −x, z+1/3; (iv) −x+y+1, −x+1, z+1/3. |