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_4130996
_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         'C16 H19 N O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_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             2014-03-13
_audit_creation_method
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.078(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7899(4)
_cell_length_b                   11.2965(5)
_cell_length_c                   13.9729(7)
_cell_measurement_reflns_used    2456
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      22.76
_cell_measurement_theta_min      2.35
_cell_volume                     1370.06(11)
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0660
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17705
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.501
_diffrn_reflns_theta_min         2.330
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0596 before and 0.0529 after correction.
The Ratio of minimum to maximum transmission is 0.9078.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     49
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0523
_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^)+(0.0334P)^2^+1.1366P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1998
_reflns_number_total             2820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b08608_si_001.cif
_cod_data_source_block           testm1
_cod_database_code               4130996
_shelxl_version_number           2013-3
_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
2. Restrained distances
 O1A-C5 \\sim O1A-C5
 with sigma of 0.003
 C7A-C6 \\sim C7B-C6
 with sigma of 0.003
 C8-C7A \\sim C8-C7B
 with sigma of 0.003
 C3-C2B \\sim C3-C2A
 with sigma of 0.003
 C2B-C1 \\sim C2A-C1
 with sigma of 0.003
 C7B-C2B \\sim C7A-C2A
 with sigma of 0.003
 C5-C4B \\sim C5-C4A
 with sigma of 0.003
 C3-C4B \\sim C4A-C3
 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
O1A \\sim O1A: within 1.7A with sigma of 0.003 and sigma for terminal atoms of
0.006
C7B \\sim C7A \\sim C3: within 1.7A with sigma of 0.003 and sigma for terminal
atoms of 0.006
C2B \\sim C2A \\sim C7B \\sim C7A: within 1.7A with sigma of 0.003 and sigma
for terminal atoms of 0.006
C4B \\sim C4A: within 1.7A with sigma of 0.003 and sigma for terminal atoms of
0.006
4. Others
 Fixed Sof: O1A(0.92347) H6AA(0.92347) H6AB(0.92347) H6BC(0.07653)
 H6BD(0.07653) H8AA(0.92347) H8AB(0.92347) H8BC(0.07653) H8BD(0.07653)
 C4A(0.92347) H4AA(0.92347) H4AB(0.92347) H3AA(0.92347) H3AB(0.92347)
 H3BC(0.07653) H3BD(0.07653) C7A(0.92347) H7A(0.92347) C2A(0.92347)
 H2A(0.92347) C2B(0.07653) H2B(0.07653) C7B(0.07653) H7B(0.07653) O1B(0.07653)
 C4B(0.07653) H4BA(0.07653) H4BB(0.07653)
5.a Ternary CH refined with riding coordinates:
 C7A(H7A), C2A(H2A), C2B(H2B), C7B(H7B)
5.b Secondary CH2 refined with riding coordinates:
 C6(H6AA,H6AB), C6(H6BC,H6BD), C1(H1A,H1B), C8(H8AA,H8AB), C8(H8BC,H8BD),
 C10(H10A,H10B), C4A(H4AA,H4AB), C3(H3AA,H3AB), C3(H3BC,H3BD), C4B(H4BA,H4BB)
5.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C14(H14), C13(H13), C15(H15)
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_shelx_res_checksum              20738
_shelx_hkl_checksum              80683