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_1571809
_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         'C42 H59 N5 O2 Zr'
_chemical_formula_sum            'C42 H59 N5 O2 Zr'
_chemical_formula_weight         757.16
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2024-05-25 deposited with the CCDC.	2024-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                79.490(2)
_cell_angle_beta                 72.182(2)
_cell_angle_gamma                67.933(2)
_cell_formula_units_Z            2
_cell_length_a                   10.6003(6)
_cell_length_b                   13.7655(7)
_cell_length_c                   15.6971(8)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.18
_cell_volume                     2014.97(19)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0484
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            59696
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.568
_diffrn_reflns_theta_min         1.601
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7222
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0512 before and 0.0486 after correction.
The Ratio of minimum to maximum transmission is 0.9680.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_description       prism
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         12351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0303P)^2^+0.7671P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0691
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10307
_reflns_number_total             12351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00636d2.cif
_cod_data_source_block           ls926
_cod_depositor_comments
'Adding full bibliography for 1571809--1571811.cif.'
_cod_database_code               1571809
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.964
_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:
 C4(H4), C1(H1), C34(H34), C31(H31), C37(H37), C40(H40)
2.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C26(H26A,H26B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C23(H23), C11(H11), C17(H17), C9(H9), C19(H19), C20(H20),
 C7(H7), C8(H8), C21(H21), C22(H22), C14(H14), C16(H16), C15(H15)
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C36(H36A,H36B,H36C), C42(H42A,H42B,H42C), C38(H38A,H38B,
 H38C), C33(H33A,H33B,H33C), C32(H32A,H32B,H32C), C30(H30A,H30B,H30C), C29(H29A,
 H29B,H29C), C41(H41A,H41B,H41C), C35(H35A,H35B,H35C)
;
_shelx_res_checksum              51413
_shelx_hkl_checksum              59222
_olex2_submission_special_instructions 'No special instructions were received'