Accessing 1,3-Dienes via Palladium-Catalyzed Allylic Alkylation of Pronucleophiles with Skipped Enynes.
Gao, Shang; Liu, Hao; Yang, Chi; Fu, Zhiyuan; Yao, Hequan; Lin, Aijun; Organic letters 19 (2017) 4710–4713; doi:10.1021/acs.orglett.7b01960

data_1547557
_publ_section_title
;
 Accessing 1,3-Dienes via Palladium-Catalyzed Allylic Alkylation of
 Pronucleophiles with Skipped Enynes.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4710
_journal_page_last               4713
_journal_paper_doi               10.1021/acs.orglett.7b01960
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C37 H32 N2 O3'
_chemical_formula_sum            'C37 H32 N2 O3'
_chemical_formula_weight         552.64
_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
_audit_creation_date             2017-04-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                113.245(5)
_cell_angle_beta                 93.815(2)
_cell_angle_gamma                94.009(4)
_cell_formula_units_Z            2
_cell_length_a                   7.3961(5)
_cell_length_b                   14.159(2)
_cell_length_c                   14.7965(10)
_cell_measurement_reflns_used    826
_cell_measurement_temperature    205
_cell_measurement_theta_max      68.27
_cell_measurement_theta_min      38.492
_cell_volume                     1412.7(2)
_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  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      205
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13633
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        61.160
_diffrn_reflns_theta_max         61.160
_diffrn_reflns_theta_min         5.601
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0732 before and 0.0386 after correction. The Ratio of minimum to maximum transmission is 0.8758. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0396
_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^)+(0.0616P)^2^+0.3071P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3916
_reflns_number_total             4140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01960_si_003.cif
_cod_data_source_block           cu_2017209_0m_a
_cod_original_cell_volume        1412.7(3)
_cod_database_code               1547557
_shelx_shelxl_version_number     2014/7
_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. Rigid bond restraints
 C24, O3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
O3 \\sim C24: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4.a Ternary CH refined with riding coordinates:
 C21(H21), C17(H17), C22(H22), C20(H20)
4.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C31(H31A,H31B)
4.c Aromatic/amide H refined with riding coordinates:
 C37(H37), C18(H18), C19(H19), C1(H1), C9(H9), C36(H36), C29(H29), C33(H33),
 C5(H5), C10(H10), C30(H30), C3(H3), C12(H12), C4(H4), C2(H2), C26(H26),
 C34(H34), C28(H28), C11(H11), C27(H27), C35(H35)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'