Mechanochemistry allows carrying out sensitive organometallic reactions in air: Glove-box-and-Schlenk-line-free synthesis of oxidative addition complexes from aryl halides and palladium(0)
Kubota, Koji; Takahashi, Rina; Ito, Hajime; Chemical Science  (2019) –; doi:10.1039/C9SC01711A

data_1550991
_publ_section_title
;
 Mechanochemistry allows carrying out sensitive organometallic reactions
 in air: Glove-box-and-Schlenk-line-free synthesis of oxidative addition
 complexes from aryl halides and palladium(0)
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01711A
_journal_year                    2019
_chemical_formula_moiety         'C136 H178 Br4 O8 P4 Pd4, 5(C H2 Cl2)'
_chemical_formula_sum            'C141 H188 Br4 Cl10 O8 P4 Pd4'
_chemical_formula_weight         3234.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-05 deposited with the CCDC.    2019-05-06 downloaded from the CCDC.
;
_cell_angle_alpha                95.3210(10)
_cell_angle_beta                 96.5900(10)
_cell_angle_gamma                92.1880(10)
_cell_formula_units_Z            2
_cell_length_a                   13.8478(2)
_cell_length_b                   18.2868(2)
_cell_length_c                   28.8141(2)
_cell_measurement_reflns_used    38370
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.3890
_cell_measurement_theta_min      2.4390
_cell_volume                     7208.41(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -16.00  12.00   0.50   17.86    --    5.00  29.00 -90.00   56
  2  \w    -74.00 -18.00   0.50   17.86    --    5.00  60.00-180.00  112
  3  \w     37.00  92.00   0.50   17.86    --    5.00  29.00 -90.00  110
  4  \w    -77.00 -25.00   0.50   17.86    --    5.00  29.00 -90.00  104
  5  \w     14.00  86.00   0.50   17.86    --    5.00  60.00-180.00  144
  6  \w   -180.00-136.00   0.50   17.86    --  -96.30  60.00   0.00   88
  7  \w    -53.00  -7.00   0.50   17.86    --  -96.30  60.00-120.00   92
  8  \w   -186.00 -76.00   0.50   17.86    --  -96.30  43.00  60.00  220
  9  \w    -94.00 -11.00   0.50   17.86    --  -96.30  60.00 150.00  166
 10  \w   -186.00-101.00   0.50   17.86    --  -96.30  60.00-120.00  170
 11  \w   -172.00-106.00   0.50   17.86    --  -96.30  60.00 150.00  132
 12  \w   -186.00 -76.00   0.50   17.86    --  -96.30  60.00  60.00  220
 13  \w   -186.00  -7.00   0.50   17.86    --  -96.30  14.00 -90.00  358
 14  \w   -182.00 -55.00   0.50   17.86    --  -96.30  43.00-120.00  254
 15  \w    -47.00 -14.00   0.50   17.86    --  -96.30  43.00-120.00   66
 16  \w    -95.00 -46.00   0.50   17.86    --  -96.30  60.00   0.00   98
 17  \w    -68.00  -7.00   0.50   17.86    --  -96.30  60.00  60.00  122
 18  \w    -34.00  -7.00   0.50   17.86    --  -96.30  43.00  60.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0286807000
_diffrn_orient_matrix_UB_12      0.0206914000
_diffrn_orient_matrix_UB_13      0.0529772000
_diffrn_orient_matrix_UB_21      -0.0227059000
_diffrn_orient_matrix_UB_22      -0.0800757000
_diffrn_orient_matrix_UB_23      0.0093570000
_diffrn_orient_matrix_UB_31      0.1059910000
_diffrn_orient_matrix_UB_32      -0.0183297000
_diffrn_orient_matrix_UB_33      -0.0055287000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            66930
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.851
_diffrn_reflns_theta_min         2.430
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    7.801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_description       plate
_exptl_crystal_F_000             3304
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.710
_refine_diff_density_min         -1.672
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1619
_refine_ls_number_reflns         27857
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0538
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0887P)^2^+12.5039P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1505
_refine_ls_wR_factor_ref         0.1539
_reflns_Friedel_coverage         0.000
_reflns_number_gt                24289
_reflns_number_total             27857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01711a2.cif
_cod_data_source_block           kbt-002-2
_cod_database_code               1550991
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'Pd P Br C H O'
_shelx_estimated_absorpt_t_max   0.860
_shelx_estimated_absorpt_t_min   0.334
_reflns_odcompleteness_completeness 98.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1AA-Cl2B
 1.73 with sigma of 0.02
 Cl2A-C1AA
 1.73 with sigma of 0.02
 C1AA-Cl1
 1.73 with sigma of 0.02
 C3-Cl3A
 1.73 with sigma of 0.02
 Cl2-C3
 1.73 with sigma of 0.02
 Cl3B-C3A
 1.73 with sigma of 0.02
 Cl6A-C3A
 1.73 with sigma of 0.02
 Cl2B-Cl1
 2.9 with sigma of 0.04
 Cl2A-Cl1
 2.9 with sigma of 0.04
 Cl3A-Cl2
 2.9 with sigma of 0.04
 Cl3B-Cl6A
 2.9 with sigma of 0.04
3. Others
 Sof(HS)=Sof(C2A)=Sof(H2AB)=Sof(H2AC)=Sof(H2AD)=Sof(C1A)=Sof(H1AB)=Sof(H1AC)=
 Sof(H1AD)=1-FVAR(1)
 Sof(H04)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=
 Sof(H2C)=FVAR(1)
 Fixed Sof: Cl4(0.5) Cl5(0.5) C4(0.5) H4A(0.5) H4B(0.5) Cl0A(0.5) Cl1A(0.5)
 C5(0.5) H5A(0.5) H5B(0.5) H1AE(0.33333) H1AF(0.33333) H1AG(0.33333)
 H1AH(0.33333) H1AI(0.33333) H1AJ(0.33333) Cl2A(0.33333) Cl2B(0.33333)
 Cl9(0.33333) Cl3A(0.5) Cl2(0.5) C3(0.5) H3A(0.5) H3B(0.5) Cl3B(0.5) C3A(0.5)
 H3AB(0.5) H3AC(0.5) Cl6A(0.5)
4.a Free rotating group:
 C04Q(Cl00)
4.b Ternary CH refined with riding coordinates:
 C015(H015), C01C(H01I), C01G(H01M), C01Z(H01Z), C027(H027), C02A(H02G),
 C02F(H02J), C02U(H1AA), C034(H034), C03F(H03U), C03I(H03Y), C03J(H03Z),
 C03Q(H0BA), C03S(H2BA), C044(H044), C04F(H04), C04F(HS)
4.c Secondary CH2 refined with riding coordinates:
 C010(H01A,H01B), C017(H01C,H01D), C018(H01E,H01F), C01A(H01G,H01H), C01D(H01J,
 H01K), C01X(H01S,H01U), C021(H02A,H02B), C026(H02C,H02D), C029(H02E,H02F),
 C02I(H02L,H02M), C02L(H02R,H02S), C02M(H02T,H02U), C02P(H02W,H02X), C02Q(H02Y,
 H), C02V(H2AA,HA), C02Z(H4AA,HB), C030(H03A,H03B), C031(H03C,H03D), C032(H03E,
 H03F), C035(H03G,H03H), C036(H03I,H03J), C039(H03K,H03L), C03A(H03M,H03N),
 C03B(H03O,H03P), C03C(H03Q,H03R), C03H(H03W,H03X), C03K(H03,HC), C03M(H6AA,HD),
  C03N(H7AA,HE), C03O(H8AA,HF), C03T(H3BA,HI), C03U(H4BA,HJ), C03V(H5BA,HK),
 C03W(H6BA,HL), C03Y(H8BA,HM), C042(H04D,H04E), C043(H04F,H04G), C048(H04K,
 H04L), C04A(H04P,H04Q), C04I(H2CA,HX), C04Q(H5CA,H8CA), C4(H4A,H4B), C5(H5A,
 H5B), C0AA(H0AB,H0AC), C1AA(H1AE,H1AF), C1AA(H1AG,H1AH), C1AA(H1AI,H1AJ),
 C3(H3A,H3B), C3A(H3AB,H3AC)
4.d Aromatic/amide H refined with riding coordinates:
 C012(H012), C01E(H01L), C01I(H01N), C01M(H01O), C01O(H01P), C01Q(H01Q),
 C01R(H01R), C01T(H01T), C01V(H01V), C01W(H01W), C01Y(H01Y), C020(H020),
 C023(H023), C025(H025), C02C(H02H), C02D(H02I), C02H(H02K), C02J(H02N),
 C02O(H02V), C02R(H02Z), C02S(H02), C02T(H0AA), C02X(H3AA), C033(H033),
 C037(H037), C038(H038), C03D(H03S), C03E(H03T), C03G(H03V), C03L(H5AA),
 C03P(H9AA), C03X(H7BA), C046(H046), C047(H047)
4.e Idealised Me refined as rotating group:
 C02K(H02O,H02P,H02Q), C03R(H1BA,HG,HH), C03Z(H9BA,HN,HO), C040(H04A,H04B,
 H04C), C045(H04H,H04I,H04J), C049(H04M,H04N,H04O), C04B(H04R,H04S,H04T),
 C04C(H04U,H04V,H04W), C04D(H04X,H04Y,HP), C04E(H04Z,HQ,HR), C04G(H0CA,HT,HU),
 C04H(H1CA,HV,HW), C04J(H3CA,HY,HZ), C04K(H4CA,H6CA,H7CA), C1(H1A,H1B,H1C),
 C2(H2A,H2B,H2C), C2A(H2AB,H2AC,H2AD), C1A(H1AB,H1AC,H1AD)
;
_shelx_res_checksum              15161
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.448
_oxdiff_exptl_absorpt_empirical_full_min 0.307