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_4130998
_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 H25 N O3'
_chemical_formula_sum            'C23 H25 N O3'
_chemical_formula_weight         363.44
_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             2016-04-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.593(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8941(3)
_cell_length_b                   18.9753(10)
_cell_length_c                   16.8998(9)
_cell_measurement_reflns_used    2798
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.13
_cell_measurement_theta_min      2.42
_cell_volume                     1886.40(17)
_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 0.996
_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  0.0833
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25803
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.040
_diffrn_reflns_theta_min         1.615
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0703 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.7948.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4561
_refine_ls_number_restraints     222
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0549
_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^)+(0.0673P)^2^+0.4427P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2609
_reflns_number_total             4561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b08608_si_007.cif
_cod_data_source_block           testm1
_cod_database_code               4130998
_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
2. Restrained distances
 C16-C15A \\sim C16-C15 \\sim C15-C14 \\sim C15A-C14
 with sigma of 0.01
 C18-C17 \\sim C17-C16 \\sim C17A-C16 \\sim C18A-C17A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C23 \\sim C17A
\\sim C18A \\sim C19A \\sim C20A \\sim C21A \\sim C22A \\sim C23A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C15A) = Uanis(C15)
4. Others
 Fixed Sof: C15(0.83194) H15A(0.83194) H15B(0.83194) H16(0.83194)
 H16A(0.16806) C17(0.83194) H17A(0.83194) H17B(0.83194) C18(0.83194)
 C19(0.83194) H19(0.83194) C20(0.83194) H20(0.83194) C21(0.83194) H21(0.83194)
 C22(0.83194) H22(0.83194) C23(0.83194) H23(0.83194) C17A(0.16806)
 H17C(0.16806) H17D(0.16806) C15A(0.16806) H15C(0.16806) H15D(0.16806)
 C18A(0.16806) C19A(0.16806) H19A(0.16806) C20A(0.16806) H20A(0.16806)
 C21A(0.16806) H21A(0.16806) C22A(0.16806) H22A(0.16806) C23A(0.16806)
 H23A(0.16806)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11), C16(H16), C16(H16A)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,H15B),
 C17(H17A,H17B), C17A(H17C,H17D), C15A(H15C,H15D)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A)
5.d Fitted hexagon refined as free rotating group:
 C18A(C19A,C20A,C21A,C22A,C23A)
;
_shelx_res_checksum              99034
_shelx_hkl_checksum              59334
_olex2_submission_special_instructions 'No special instructions were received'