Carbon Isotope Labeling Strategy for β-Amino Acid Derivatives via Carbonylation of Azanickellacycles.
Ravn, Anne K.; Vilstrup, Maria B. T.; Noerby, Peter; Nielsen, Dennis U.; Daasbjerg, Kim; Skrydstrup, Troels; Journal of the American Chemical Society 141 (2019) 11821–11826; doi:10.1021/jacs.9b05934

data_4128549
_publ_section_title
;
 Carbon Isotope Labeling Strategy for \b-Amino Acid Derivatives via
 Carbonylation of Azanickellacycles.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11821
_journal_page_last               11826
_journal_paper_doi               10.1021/jacs.9b05934
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C29 H25 N3 Ni O3 S'
_chemical_formula_sum            'C29 H25 N3 Ni O3 S'
_chemical_formula_weight         554.29
_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             2018-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                84.176(3)
_cell_angle_beta                 83.985(3)
_cell_angle_gamma                71.067(3)
_cell_formula_units_Z            2
_cell_length_a                   10.6334(8)
_cell_length_b                   10.7865(8)
_cell_length_c                   11.1203(8)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.62
_cell_measurement_theta_min      2.25
_cell_volume                     1196.73(15)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            98985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         27.083
_diffrn_reflns_theta_min         1.457
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.496
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0912 before and 0.0524 after correction. The Ratio of minimum to maximum transmission is 0.9529. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'lusterous dark red'
_exptl_crystal_colour_lustre     lusterous
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.266
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         10684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0337
_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^)+(0.0349P)^2^+0.6927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0859
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9140
_reflns_number_total             10684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05934_si_002.cif
_cod_data_source_block           JACS_AnneRavn_16
_cod_database_code               4128549
_shelx_shelxl_version_number     2016/6
_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:
 C00J(H00J)
2.b Secondary CH2 refined with riding coordinates:
 C00O(H00A,H00B), C00R(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00G(H00G), C00H(H00H), C00I(H00I), C00L(H00L), C00M(H00M),
 C00N(H00N), C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010)
2.d Idealised Me refined as rotating group:
 C011(H01A,H01B,H01C)
;
_olex2_date_sample_data_collection 2018-12-06
_olex2_submission_special_instructions 'No special instructions were received'