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_4130995
_publ_section_title
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 New Initiation Modes for Directed Carbonylative C-C Bond Activation:
 Rhodium-Catalyzed (3 + 1 + 2) Cycloadditions of Aminomethylcyclopropanes.
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_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         'C15 H21 N O3 S'
_chemical_formula_sum            'C15 H21 N O3 S'
_chemical_formula_weight         295.39
_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             2016-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.9091(13)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.1147(4)
_cell_length_b                   9.2175(2)
_cell_length_c                   18.0021(4)
_cell_measurement_reflns_used    5260
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.31
_cell_volume                     2929.88(11)
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0240
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13092
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.934
_diffrn_reflns_theta_min         2.307
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0471 before and 0.0373 after correction.
The Ratio of minimum to maximum transmission is 0.9370.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.416
_exptl_crystal_size_min          0.262
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3507
_refine_ls_number_restraints     276
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0375
_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^)+(0.0575P)^2^+3.0571P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2999
_reflns_number_total             3507
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b08608_si_010.cif
_cod_data_source_block           testm1
_cod_database_code               4130995
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.891
_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, All O(H) groups
2. Restrained distances
 C5-C2 \\sim C5A-C2A \\sim C3-C2 \\sim C3A-C2A \\sim C8A-C3A \\sim C8-C3 \\sim
C8-C7 \\sim C8A-C7A \\sim C7A-
 C6A \\sim C7-C6 \\sim C6-C5 \\sim C6A-C5A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O3 \\sim C8 \\sim C5 \\sim C2 \\sim C6 \\sim C7 \\sim C3 \\sim C2A \\sim C3A
\\sim C6A \\sim C7A \\sim O3A \\sim C8A \\sim C5A: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.008
4. Others
 Fixed Sof: O3(0.65128) H3(0.65128) H4AA(0.65128) H4AB(0.65128) H4BC(0.34872)
 H4BD(0.34872) H1AA(0.65128) H1AB(0.65128) H1BC(0.34872) H1BD(0.34872)
 C8(0.65128) H8A(0.65128) H8B(0.65128) C5(0.65128) H5A(0.65128) H5B(0.65128)
 C2(0.65128) H2(0.65128) C6(0.65128) H6A(0.65128) H6B(0.65128) C7(0.65128)
 H7(0.65128) C3(0.65128) H3A(0.65128) C2A(0.34872) H2A(0.34872) C3A(0.34872)
 H3AA(0.34872) C6A(0.34872) H6AA(0.34872) H6AB(0.34872) C7A(0.34872)
 H7A(0.34872) O3A(0.34872) H3AB(0.34872) C8A(0.34872) H8AA(0.34872)
 H8AB(0.34872) C5A(0.34872) H5AA(0.34872) H5AB(0.34872)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7), C3(H3A), C2A(H2A), C3A(H3AA), C7A(H7A)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4AA,H4AB), C4(H4BC,H4BD), C1(H1AA,H1AB), C1(H1BC,H1BD), C8(H8A,H8B),
 C5(H5A,H5B), C6(H6A,H6B), C6A(H6AA,H6AB), C8A(H8AA,H8AB), C5A(H5AA,H5AB)
5.c Aromatic/amide H refined with riding coordinates:
 C0AA(H0AA), C11(H11), C14(H14), C13(H13)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
5.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O3A(H3AB)
;
_shelx_res_checksum              71489
_shelx_hkl_checksum              98082
_olex2_submission_special_instructions 'No special instructions were received'