Diastereoselective Pd(II)-Catalyzed sp<sup>3</sup> C-H Arylation Followed by Ring Opening of Cyclopropanecarboxamides: Construction of anti β-Acyloxy Carboxamide Derivatives.
Gopalakrishnan, Bojan; Mohan, Sruthi; Parella, Ramarao; Babu, Srinivasarao Arulananda; The Journal of organic chemistry 81 (2016) 8988–9005; doi:10.1021/acs.joc.6b01635

data_4037162
_publ_section_title
;
 Diastereoselective Pd(II)-Catalyzed sp<sup>3</sup> C-H Arylation Followed
 by Ring Opening of Cyclopropanecarboxamides: Construction of anti
 \b-Acyloxy Carboxamide Derivatives.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8988
_journal_page_last               9005
_journal_paper_doi               10.1021/acs.joc.6b01635
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C39 H41 N2 O3'
_chemical_formula_sum            'C39 H41 N2 O3'
_chemical_formula_weight         585.74
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-21
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_cell_angle_alpha                82.610(12)
_cell_angle_beta                 78.913(13)
_cell_angle_gamma                66.044(9)
_cell_formula_units_Z            2
_cell_length_a                   11.085
_cell_length_b                   12.4569(4)
_cell_length_c                   13.1946(6)
_cell_measurement_temperature    298
_cell_volume                     1631.35(16)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14457
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.023
_diffrn_reflns_theta_min         3.152
_diffrn_source                   'Sealed Tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       block
_exptl_crystal_F_000             626
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.198
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0799
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1638P)^2^+0.4665P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2384
_refine_ls_wR_factor_ref         0.2582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4464
_reflns_number_total             5757
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01635_si_003.cif
_cod_data_source_block           shelxl
_cod_database_code               4037162
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4A), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C40(H40A,H40B), C1(H1A,H1B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4), C2(H2), C8(H8), C9(H9), C12(H12), C13(H13), C17(H17), C21(H21),
 C22(H22), C24(H24), C25(H25), C27(H27), C28(H28), C31(H31), C32(H32), C33(H33),
  C34(H34), C35(H35)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C30(H30A,H30B,H30C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C)
;
_shelx_res_checksum              82201
_shelx_hkl_checksum              13742
_olex2_submission_special_instructions 'No special instructions were received'