Ligandless Palladium-Catalyzed Regioselective Direct C-H Arylation of Imidazo[1,2-a]imidazole Derivatives.
Grosse, Sandrine; Pillard, Christelle; Massip, Stéphane; Marchivie, Mathieu; Jarry, Christian; Bernard, Philippe; Guillaumet, Gérald; The Journal of organic chemistry 80 (2015) 8539–8551; doi:10.1021/acs.joc.5b00534

data_4036202
_publ_section_title
;
 Ligandless Palladium-Catalyzed Regioselective Direct C-H Arylation of
 Imidazo[1,2-a]imidazole Derivatives.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8539
_journal_page_last               8551
_journal_paper_doi               10.1021/acs.joc.5b00534
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C28 H27 N3 O'
_chemical_formula_sum            'C28 H27 N3 O'
_chemical_formula_weight         421.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2013-09-30
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_audit_update_record
;
????
;
_cell_angle_alpha                90
_cell_angle_beta                 92.902(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.5931(2)
_cell_length_b                   10.9324(2)
_cell_length_c                   18.2371(13)
_cell_measurement_temperature    293
_cell_volume                     2308.41(18)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Rigaku RAXIS Rapid'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            46605
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.209
_diffrn_reflns_theta_min         7.267
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku/MSC Inc., 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.239
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.177
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0790
_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^)+(0.0500P)^2^+1.8000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1781
_refine_ls_wR_factor_ref         0.1897
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2785
_reflns_number_total             4201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00534_si_002.cif
_cod_data_source_block           san758
_cod_database_code               4036202
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.904
_shelx_estimated_absorpt_t_min   0.873
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H24c)=Sof(H24d)=Sof(C32b)=Sof(H32a)=Sof(H32b)=Sof(H32c)=Sof(O31b)=
 Sof(C25b)=Sof(C30b)=Sof(H30b)=Sof(C29b)=Sof(H29b)=Sof(C28b)=Sof(C27b)=
 Sof(H27b)=Sof(C26b)=Sof(H26b)=1-FVAR(1)
 Sof(C25a)=Sof(C30a)=Sof(H30a)=Sof(C29a)=Sof(H29a)=Sof(C28a)=Sof(C27a)=
 Sof(H27a)=Sof(C26a)=Sof(H26a)=Sof(H24a)=Sof(H24b)=Sof(O31a)=Sof(C32a)=
 Sof(H32d)=Sof(H32e)=Sof(H32f)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C24(H24a,H24b), C24(H24c,H24d)
3.b Aromatic/amide H refined with riding coordinates:
 C30a(H30a), C29a(H29a), C27a(H27a), C26a(H26a), C6(H6), C22(H22), C21(H21),
 C11(H11), C18(H18), C12(H12), C19(H19), C14(H14), C15(H15), C30b(H30b),
 C29b(H29b), C27b(H27b), C26b(H26b)
3.c Fitted hexagon refined as free rotating group:
 C25a(C30a,C29a,C28a,C27a,C26a), C25b(C30b,C29b,C28b,C27b,C26b)
3.d Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C16(H16a,H16b,H16c), C23(H23a,H23b,H23c), C32b(H32a,H32b,
 H32c), C32a(H32d,H32e,H32f)
;