Conversion of Arylboronic Acids to Tetrazoles Catalyzed by ONO Pincer-Type Palladium Complex.
Vignesh, Arumugam; Bhuvanesh, Nattamai S. P.; Dharmaraj, Nallasamy; The Journal of organic chemistry 82 (2017) 887–892; doi:10.1021/acs.joc.6b02277

data_4032101
_publ_section_title
;
 Conversion of Arylboronic Acids to Tetrazoles Catalyzed by ONO
 Pincer-Type Palladium Complex.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              887
_journal_page_last               892
_journal_paper_doi               10.1021/acs.joc.6b02277
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C37 H35 N2 O2 P Pd'
_chemical_formula_sum            'C37 H35 N2 O2 P Pd'
_chemical_formula_weight         677.04
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-10-29
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_audit_update_record
;
2016-05-02 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.275(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.702(3)
_cell_length_b                   19.376(6)
_cell_length_c                   18.853(6)
_cell_measurement_reflns_used    3716
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      21.027
_cell_measurement_theta_min      2.178
_cell_volume                     3153.2(18)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      110.15
_diffrn_measured_fraction_theta_full 0.597
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1320
_diffrn_reflns_av_unetI/netI     0.0859
_diffrn_reflns_Laue_measured_fraction_full 0.597
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20665
_diffrn_reflns_point_group_measured_fraction_full 0.597
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         21.058
_diffrn_reflns_theta_min         2.102
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.675
_exptl_absorpt_correction_T_max  0.7440
_exptl_absorpt_correction_T_min  0.6423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0892 before and 0.0771 after correction.
The Ratio of minimum to maximum transmission is 0.8633.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.822
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         3407
_refine_ls_number_restraints     90
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0169P)^2^+14.3503P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0982
_refine_ls_wR_factor_ref         0.1133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2342
_reflns_number_total             3407
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02277_si_002.cif
_cod_data_source_block           pddsbh
_cod_depositor_comments          'Adding full bibliography for 4032101.cif.'
_cod_original_cell_volume        3153.0(16)
_cod_database_code               4032101
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.917
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9A-C8 = C9-C8 = C9-C10 = C9A-C10A = C8-C11 = C8-C11A = C12-C11 = C12A-C11A
 1.54 with sigma of 0.01
 C8-C10 = C8-C10A = C8-C12 = C8-C12A
 2.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C11A \\sim C9A \\sim C10A \\sim C10 \\sim C9 \\sim C12 \\sim C12A \\sim C11:
within 1.7A with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 C11A, C9A, C10A, C10, C9, C12, C12A, C11
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
5. Others
 Sof(H8B)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=
 Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(H12D)=Sof(H12E)=Sof(H12F)=1-FVAR(1)
 Sof(H8A)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C8(H8A), C8(H8B)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C9A(H9AA,H9AB), C11A(H11C,H11D)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C6(H6), C7(H7), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28),
  C29(H29), C30(H30), C31(H31), C33(H33), C34(H34), C35(H35), C36(H36), C37(H37)
6.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C10A(H10D,H10E,H10F), C12A(H12D,
 H12E,H12F)
;
_shelx_res_checksum              7711
_olex2_submission_special_instructions 'No special instructions were received'