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_1571811
_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         'C39 H63 N5 O2 Si Zr, C7 H8'
_chemical_formula_sum            'C46 H71 N5 O2 Si Zr'
_chemical_formula_weight         845.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-10-28
_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                90
_cell_angle_beta                 111.514(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   34.527(4)
_cell_length_b                   10.5749(13)
_cell_length_c                   27.352(3)
_cell_measurement_reflns_used    9264
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.26
_cell_volume                     9291.0(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 0.998
_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  0.0661
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_number            14182
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.527
_diffrn_reflns_theta_min         1.268
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 240133 reflections, Rint = 0.0656
 (97937 with I > 3sig(I), Rint = 0.0429)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       irregular
_exptl_crystal_F_000             3616
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         14182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0336P)^2^+14.1533P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0875
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11412
_reflns_number_total             14182
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00636d2.cif
_cod_data_source_block           mo_ls938_0m_4dom2
_cod_depositor_comments
'Adding full bibliography for 1571809--1571811.cif.'
_cod_original_cell_volume        9291(2)
_cod_database_code               1571811
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.931
_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), C3(H3), C28(H28), C1(H1), C37(H37), C31(H31), C5(H5), C34(H34)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C2(H2A,H2B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C13(H13), C11(H11), C17(H17), C15(H15), C16(H16), C42(H42), C8(H8),
 C9(H9), C14(H14), C10(H10), C44(H44), C46(H46), C45(H45), C43(H43)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C26(H26A,H26B,H26C), C35(H35A,H35B,H35C), C30(H30A,H30B,
 H30C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C), C39(H39A,H39B,H39C), C32(H32A,
 H32B,H32C), C33(H33A,H33B,H33C), C19(H19A,H19B,H19C), C29(H29A,H29B,H29C),
 C38(H38A,H38B,H38C), C36(H36A,H36B,H36C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              46196
_shelx_hkl_checksum              70027
_olex2_submission_special_instructions 'No special instructions were received'