Palladium/Norbornene Cooperative Catalysis To Access Tetrahydronaphthalenes and Indanes with a Quaternary Center
Liu, Ze-Shui; Qian, Guangyin; Gao, Qianwen; Wang, Peng; Cheng, Hong-Gang; Wei, Qiang; Liu, Qi; Zhou, Qianghui; ACS Catalysis 8 (2018) 4783–; doi:10.1021/acscatal.8b00975

data_4515635
_publ_section_title
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 Palladium/Norbornene Cooperative Catalysis To Access
 Tetrahydronaphthalenes and Indanes with a Quaternary Center
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              4783
_journal_paper_doi               10.1021/acscatal.8b00975
_journal_volume                  8
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Br, C15 H22 N O'
_chemical_formula_sum            'C15 H22 Br N O'
_chemical_formula_weight         312.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.736(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5964(3)
_cell_length_b                   16.0907(6)
_cell_length_c                   12.1098(5)
_cell_measurement_reflns_used    9505
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.40
_cell_measurement_theta_min      2.72
_cell_volume                     1458.88(10)
_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)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            64689
_diffrn_reflns_theta_full        37.69
_diffrn_reflns_theta_max         37.69
_diffrn_reflns_theta_min         1.71
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.807
_exptl_absorpt_correction_T_max  0.7474
_exptl_absorpt_correction_T_min  0.6081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.780
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         15437
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.0750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0963
_reflns_number_gt                9304
_reflns_number_total             15437
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cs8b00975_si_003.cif
_cod_data_source_block           1
_cod_database_code               4515635
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), N1(H1), C23(H23), N2(H2B)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C7(H7A,H7B), C13(H13A,H13B), C9(H9A,H9B), C12(H12A,H12B),
 C24(H24A,H24B), C29(H29A,H29B), C22(H22A,H22B), C27(H27A,H27B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C17(H17), C20(H20), C21(H21), C3(H3), C2(H2)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C26(H26A,H26B,H26C), C15(H15A,H15B,H15C), C30(H30A,H30B,
 H30C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O1(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'