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_4130994
_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         'C23 H27 N O4 S'
_chemical_formula_sum            'C23 H27 N O4 S'
_chemical_formula_weight         413.51
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.2982(5)
_cell_length_b                   17.6122(11)
_cell_length_c                   25.4699(15)
_cell_measurement_reflns_used    3978
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.27
_cell_measurement_theta_min      2.31
_cell_volume                     4171.0(4)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.963
_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  0.1500
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            58820
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.674
_diffrn_reflns_theta_min         1.599
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0921 before and 0.0714 after correction.
The Ratio of minimum to maximum transmission is 0.7997.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_description       plate
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.339
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3955
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0487
_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^)+(0.0496P)^2^+2.6515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2630
_reflns_number_total             3955
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b08608_si_004.cif
_cod_data_source_block           testo1
_cod_database_code               4130994
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.940
_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. Uiso/Uaniso restraints and constraints
Uanis(C9) = Uanis(C9A)
3. Others
 Fixed Sof: H8AA(0.89098) H8AB(0.89098) H8BC(0.10902) H8BD(0.10902)
 C9(0.89098) H9(0.89098) H10(0.89098) H10A(0.10902) H12A(0.89098) H12B(0.89098)
 H12C(0.10902) H12D(0.10902) C9A(0.10902) H9A(0.10902)
4.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C10(H10A), C11(H11), C9A(H9A)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8AA,H8AB), C8(H8BC,H8BD), C12(H12A,H12B), C12(H12C,H12D), C13(H13A,H13B),
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23)
4.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              39887
_shelx_hkl_checksum              65064
_olex2_submission_special_instructions 'No special instructions were received'