Understanding mechanism driven regioselectivity in zirconium-catalysed hydroaminoalkylation: homoallylic amines from conjugated dienes.
Nuñez Bahena, Erick; Hosseini, Kimia; Curto, Sheila Galván; Schafer, Laurel L.; Chemical science 15 (2024) 10571–10576; doi:10.1039/d4sc00636d

data_1571810
_publ_section_title
;
 Understanding mechanism driven regioselectivity in zirconium-catalysed
 hydroaminoalkylation: homoallylic amines from conjugated dienes.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              10571
_journal_page_last               10576
_journal_paper_doi               10.1039/d4sc00636d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C37 H57 N5 O2 Zr'
_chemical_formula_sum            'C37 H57 N5 O2 Zr'
_chemical_formula_weight         695.09
_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     dual
_audit_creation_date             2021-10-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2024-05-25 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                96.630(2)
_cell_angle_beta                 103.052(2)
_cell_angle_gamma                109.933(2)
_cell_formula_units_Z            2
_cell_length_a                   10.4694(7)
_cell_length_b                   13.7275(10)
_cell_length_c                   14.5277(11)
_cell_measurement_reflns_used    9931
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.59
_cell_measurement_theta_min      2.40
_cell_volume                     1869.4(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53872
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.639
_diffrn_reflns_theta_min         1.614
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0606 before and 0.0509 after correction.
The Ratio of minimum to maximum transmission is 0.8751.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_description       irregular
_exptl_crystal_F_000             740
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.887
_refine_diff_density_min         -0.843
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         11493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0458P)^2^+0.1789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9331
_reflns_number_total             11493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00636d2.cif
_cod_data_source_block           mo_ls933_0m
_cod_depositor_comments
'Adding full bibliography for 1571809--1571811.cif.'
_cod_database_code               1571810
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.871
_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.a Ternary CH refined with riding coordinates:
 C26(H26), C3(H3), C32(H32), C29(H29), C1(H1), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C5(H5A,H5B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C18(H18), C10(H10), C11(H11), C9(H9), C15(H15), C17(H17),
 C14(H14), C16(H16)
2.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C28(H28A,H28B,
 H28C), C25(H25A,H25B,H25C), C33(H33A,H33B,H33C), C24(H24A,H24B,H24C), C27(H27A,
 H27B,H27C), C37(H37A,H37B,H37C), C6(H6A,H6B,H6C), C36(H36A,H36B,H36C)
;
_shelx_res_checksum              30524
_shelx_hkl_checksum              63700
_olex2_submission_special_instructions 'No special instructions were received'