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_4130991
_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         'C19 H27 N O3 S'
_chemical_formula_sum            'C19 H27 N O3 S'
_chemical_formula_weight         349.47
_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
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-06-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.444(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.7207(9)
_cell_length_b                   12.1769(3)
_cell_length_c                   10.4303(3)
_cell_measurement_reflns_used    2248
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.45
_cell_measurement_theta_min      2.61
_cell_volume                     3617.04(18)
_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(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0596
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15701
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.939
_diffrn_reflns_theta_min         1.819
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0659 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.7778.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_description       plate
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4345
_refine_ls_number_restraints     132
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0519
_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^)+(0.0544P)^2^+3.6940P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1312
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2987
_reflns_number_total             4345
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b08608_si_008.cif
_cod_data_source_block           testm1
_cod_database_code               4130991
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C6A
 1.53 with sigma of 0.01
 C6A-C5
 1.59 with sigma of 0.01
 C9A-C10A = C9A-C6A
 1.55 with sigma of 0.01
 C11A-C10A = C12A-C11A
 1.55 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C6 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C6A \\sim C9A \\sim C10A \\sim
C12A \\sim C11A: within 2A with sigma of 0.003 and sigma for terminal atoms of
0.006
Uanis(C11) = Uanis(C11A)
4. Others
 Fixed Sof: H5AA(0.79981) H5AB(0.79981) H5BC(0.20019) H5BD(0.20019)
 C6(0.79981) H6(0.79981) C9(0.79981) H9A(0.79981) H9B(0.79981) C10(0.79981)
 H10A(0.79981) H10B(0.79981) C11(0.79981) H11A(0.79981) H11B(0.79981)
 C12(0.79981) H12A(0.79981) H12B(0.79981) H12C(0.79981) C6A(0.20019)
 H6A(0.20019) C9A(0.20019) H9AA(0.20019) H9AB(0.20019) C10A(0.20019)
 H10C(0.20019) H10D(0.20019) C12A(0.20019) H12D(0.20019) H12E(0.20019)
 H12F(0.20019) C11A(0.20019) H11C(0.20019) H11D(0.20019)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C6A(H6A)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5AA,H5AB), C5(H5BC,H5BD), C8(H8A,H8B), C9(H9A,
 H9B), C10(H10A,H10B), C11(H11A,H11B), C9A(H9AA,H9AB), C10A(H10C,H10D),
 C11A(H11C,H11D)
5.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C17(H17), C18(H18)
5.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C), C12A(H12D,H12E,H12F)
;
_shelx_res_checksum              81948
_shelx_hkl_checksum              40091
_olex2_submission_special_instructions 'No special instructions were received'