New Initiation Modes for Directed Carbonylative C-C Bond Activation: Rhodium-Catalyzed (3 + 1 + 2) Cycloadditions of Aminomethylcyclopropanes.
Wang, Gang-Wei; McCreanor, Niall G.; Shaw, Megan H.; Whittingham, William G.; Bower, John F.; Journal of the American Chemical Society 138 (2016) 13501–13504; doi:10.1021/jacs.6b08608

data_4130992
_publ_section_title
;
 New Initiation Modes for Directed Carbonylative C-C Bond Activation:
 Rhodium-Catalyzed (3 + 1 + 2) Cycloadditions of Aminomethylcyclopropanes.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13501
_journal_page_last               13504
_journal_paper_doi               10.1021/jacs.6b08608
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C16 H21 N O3 S'
_chemical_formula_sum            'C16 H21 N O3 S'
_chemical_formula_weight         307.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-04-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.722(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6580(8)
_cell_length_b                   5.6045(3)
_cell_length_c                   20.1680(13)
_cell_measurement_reflns_used    3037
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.12
_cell_measurement_theta_min      2.37
_cell_volume                     1529.79(16)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16726
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.295
_diffrn_reflns_theta_min         1.505
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0643 before and 0.0522 after correction.
The Ratio of minimum to maximum transmission is 0.8657.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.383
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         3085
_refine_ls_number_restraints     509
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0371P)^2^+0.7550P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1011
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2439
_reflns_number_total             3085
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b08608_si_009.cif
_cod_data_source_block           wgw2154
_cod_database_code               4130992
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Restrained distances
 C14-C15 \\sim C14A-C15A
 with sigma of 0.01
 C8-C14 \\sim C8A-C14A
 with sigma of 0.01
 C8-C15 \\sim C8A-C15A
 with sigma of 0.01
 C8-C10 \\sim C8A-C10A
 with sigma of 0.01
 C10-C14 \\sim C10A-C14A
 with sigma of 0.01
 C8-C9 \\sim C8A-C9A
 with sigma of 0.01
 C9-C14 \\sim C9A-C14A
 with sigma of 0.01
 C9-C15 \\sim C9A-C15A
 with sigma of 0.01
 C9-C10 \\sim C9A-C10A
 with sigma of 0.01
 C10-C11 \\sim C10A-C11A
 with sigma of 0.01
 C9-C11 \\sim C9A-C11A
 with sigma of 0.01
 C13-C14 \\sim C13A-C14A
 with sigma of 0.01
 C9-C13 \\sim C9A-C13A
 with sigma of 0.01
 C13-C15 \\sim C13A-C15A
 with sigma of 0.01
 C11-C13 \\sim C11A-C13A
 with sigma of 0.01
 C12-C14 \\sim C12A-C14A
 with sigma of 0.01
 C10-C12 \\sim C10A-C12A
 with sigma of 0.01
 C11-C12 \\sim C11A-C12A
 with sigma of 0.01
 C12-C13 \\sim C12A-C13A
 with sigma of 0.01
 N1-C8 \\sim N1A-C8A
 with sigma of 0.01
 C15-N1 \\sim C15A-N1A
 with sigma of 0.01
 C14-N1 \\sim C14A-N1A
 with sigma of 0.01
 C9-N1 \\sim C9A-N1A
 with sigma of 0.01
 S1-N1 \\sim S1A-N1A
 with sigma of 0.01
 S1-O1 \\sim S1A-O1A
 with sigma of 0.01
 S1-O2 \\sim S1A-O2A
 with sigma of 0.01
 C12-O3 \\sim C12A-O3A
 with sigma of 0.01
 C11-O3 \\sim C11A-O3A \\sim C13-O3 \\sim C13A-O3A
 with sigma of 0.01
 C13-C16 \\sim C13A-C16A
 with sigma of 0.01
 C16-O3 \\sim C16A-O3A
 with sigma of 0.01
 C12-C16 \\sim C12A-C16A \\sim C14-C16 \\sim C14A-C16A
 with sigma of 0.01
2. Uiso/Uaniso restraints and constraints
C8 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim
C16 \\sim N1 \\sim O1 \\sim O2 \\sim O3 \\sim S1 \\sim C8A \\sim C9A \\sim C10A
\\sim C11A \\sim C12A \\sim C13A \\sim C14A \\sim C15A \\sim C16A \\sim N1A
\\sim O1A \\sim O2A \\sim O3A \\sim S1A: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
3. Others
 Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10C)=Sof(H10D)=
 Sof(C11A)=Sof(H11C)=Sof(H11D)=Sof(C12A)=Sof(C13A)=Sof(H13A)=Sof(C14A)=
 Sof(H14A)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16D)=Sof(H16E)=
 Sof(H16F)=Sof(N1A)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(S1A)=1-FVAR(1)
 Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10A)=Sof(H10B)=
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(N1)=
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(S1)=FVAR(1)
;
_shelx_res_checksum              2932
_shelx_hkl_checksum              56987
_olex2_submission_special_instructions 'No special instructions were received'