Exploiting natural complexity for substrate controlled regioselectivity and stereoselectivity in tantalum catalysed hydroaminoalkylation
Zheng, Cameron H. M.; Nadeau, Ben E.; Trajano, Heather L.; Schafer, Laurel L.; Green Chemistry 26 (2024) 9729–9736; doi:10.1039/D4GC01614A

data_7249254
_publ_section_title
;
 Exploiting natural complexity for substrate controlled regioselectivity
 and stereoselectivity in tantalum catalysed hydroaminoalkylation
;
_journal_issue                   18
_journal_name_full               'Green Chemistry'
_journal_page_first              9729
_journal_page_last               9736
_journal_paper_doi               10.1039/D4GC01614A
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'Cl, C21.924 H34.772 Cl0.91 N'
_chemical_formula_sum            'C22 H35 Cl2 N'
_chemical_formula_weight         384.41
_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
_audit_creation_date             2024-03-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-03-29 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.880(2)
_cell_angle_beta                 100.392(2)
_cell_angle_gamma                102.199(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6390(5)
_cell_length_b                   9.6446(5)
_cell_length_c                   15.2699(9)
_cell_measurement_reflns_used    9917
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.41
_cell_measurement_theta_min      2.49
_cell_volume                     1079.90(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.999
_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_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3562
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.435
_diffrn_reflns_theta_max         24.435
_diffrn_reflns_theta_min         1.358
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.306
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0423 before and 0.0376 after correction.
 
For component 2:
 wR2(int) was 0.0580 before and 0.0462 after correction.
 The Ratio of minimum to maximum transmission is 0.82.

Final HKLF 4 output contains 25931 reflections, Rint = 0.0487
 (14021 with I > 3sig(I), Rint = 0.0377)
;
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3562
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0496
_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^)+(0.0460P)^2^+1.0791P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2910
_reflns_number_total             3562
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4gc01614a2.cif
_cod_data_source_block           mo_ls999_0m
_cod_depositor_comments
'Adding full bibliography for 7249254--7249255.cif.'
_cod_database_code               7249254
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.947
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.643(2)
 0.357(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 C7-C8A \\sim C7-C8B
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C8B) = Uanis(Cl2)
5. Others
 Sof(C8B)=Sof(H8BA)=Sof(H8BB)=Sof(H8BC)=FVAR(1)
 Fixed Sof: Cl2(0.71) C8A(0.62) H8AA(0.62) H8AB(0.62) H8AC(0.62) Cl2B(0.2)
6.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C4(H4A,H4B), C5(H5A,H5B), C16(H16A,H16B), C10(H10A,
 H10B), C9(H9A,H9B), C6(H6A,H6B)
6.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C22(H22), C19(H19), C21(H21), C20(H20), C15(H15), C14(H14)
6.c Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C3(H3A,H3B,H3C), C13(H13A,H13B,H13C), C12(H12A,H12B,
 H12C), C8B(H8BA,H8BB,H8BC)
;
_shelx_res_checksum              90594
_shelx_hkl_checksum              83878
_olex2_submission_special_instructions 'No special instructions were received'