A general synthesis of unnatural α-amino acids by iron-catalysed olefin–olefin coupling via generated radicals
Larionov, Vladimir A.; Stoletova, Nadezhda V.; Kovalev, Vladislav I.; Smol'yakov, Alexander F.; Savel'yeva, Tat'yana F.; Maleev, Victor I.; Organic Chemistry Frontiers 6 (2019) 1094–; doi:10.1039/C9QO00108E

data_1554736
_publ_section_title
;
 A general synthesis of unnatural \a-amino acids by iron-catalysed
 olefin--olefin coupling via generated radicals
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1094
_journal_paper_doi               10.1039/C9QO00108E
_journal_volume                  6
_journal_year                    2019
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C37 H37 N3 Ni O3, H2 O'
_chemical_formula_sum            'C37 H39 N3 Ni O4'
_chemical_formula_weight         648.42
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-22 deposited with the CCDC.	2019-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.1810(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8460(4)
_cell_length_b                   12.0451(5)
_cell_length_c                   14.2648(6)
_cell_measurement_reflns_used    6177
_cell_measurement_temperature    120
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      2.20
_cell_volume                     1587.89(11)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20201
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.683
_diffrn_reflns_theta_min         1.521
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0675 before and 0.0565 after correction. The Ratio of minimum to maximum transmission is 0.9241. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       prism
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.774
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 3368 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         8940
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0447P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.908
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                7901
_reflns_number_total             8940
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00108e2.cif
_cod_data_source_block           p
_cod_depositor_comments
;

2025-06-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         324.21
_cod_original_formula_moiety         '0.5(C37 H37 N3 Ni O3), 0.5(H2 O)'
_cod_original_formula_units_Z            4
_cod_original_formula_sum        'C18.50 H19.50 N1.50 Ni0.50 O2'
_cod_database_code               1554736
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.914
_shelx_estimated_absorpt_t_min   0.853
_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, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C27(H27)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B)
2.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C33(H33), C34(H34),
  C35(H35), C36(H36), C37(H37)
2.e Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              6735
_shelx_hkl_checksum              46961
_olex2_submission_special_instructions 'No special instructions were received'