Palladium-catalyzed arylation of β-methylene C(sp3)–H bonds at room temperature: desymmetrization of simple cycloalkyl carboxylic acids
Nack, W. A.; Wang, B.; Wu, X.; Jiao, R.; He, G.; Chen, G.; Organic Chemistry Frontiers 3 (2016) 561–; doi:10.1039/C5QO00421G

data_1553230
_publ_section_title
;
 Palladium-catalyzed arylation of \b-methylene C(sp3)--H bonds at room
 temperature: desymmetrization of simple cycloalkyl carboxylic acids
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              561
_journal_paper_doi               10.1039/C5QO00421G
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C20 H15 N3 O3'
_chemical_formula_sum            'C20 H15 N3 O3'
_chemical_formula_weight         345.35
_chemical_name_systematic        Wun1m
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-01-15
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-02-01 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.915(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.6461(19)
_cell_length_b                   10.7230(15)
_cell_length_c                   22.268(4)
_cell_measurement_reflns_used    3041
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.023
_cell_measurement_theta_min      2.416
_cell_volume                     3258.0(9)
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  Parallel,graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12321
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.83
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           32.0
_diffrn_source_power             1.6
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.678210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
? was used for absorption correction.
R(int) was 0.0374 before and 0.0234 after correction.
The Ratio of minimum to maximum transmission is 0.6782.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4046
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.199
_refine_ls_R_factor_all          0.1590
_refine_ls_R_factor_gt           0.1530
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3373
_refine_ls_wR_factor_ref         0.3402
_reflns_number_gt                3836
_reflns_number_total             4046
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5qo00421g2.cif
_cod_data_source_block           wun1m
_cod_database_code               1553230
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C12(H12), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C2(H2), C4(H4), C9(H9), C8(H8), C7(H7), C18(H18), C3(H3), C17(H17),
 C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'