Formal Substitution of Bromocyclopropanes with Nitrogen Nucleophiles
Joseph E. Banning; Jacob Gentillon; Pavel G. Ryabchuk; Anthony R. Prosser; Andrew Rogers; Andrew Edwards; Andrew Holtzen; Ivan A. Babkov; Marina Rubina; Michael Rubin; Journal of Organic Chemistry 78 (2013) 7601–7616; doi:10.1021/jo4011798

data_4028468
_publ_section_title
;
 Formal Substitution of Bromocyclopropanes with Nitrogen Nucleophiles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7601
_journal_page_last               7616
_journal_paper_doi               10.1021/jo4011798
_journal_volume                  78
_journal_year                    2013
_chemical_formula_sum            'C19 H30 N2 O3 S'
_chemical_formula_weight         366.51
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                70.290(4)
_cell_angle_beta                 75.181(5)
_cell_angle_gamma                85.869(4)
_cell_formula_units_Z            4
_cell_length_a                   9.8452(16)
_cell_length_b                   12.615(2)
_cell_length_c                   17.535(3)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.94
_cell_measurement_theta_min      2.76
_cell_volume                     1981.8(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Helios multilayer optics'
_diffrn_radiation_source         'Bruker MicroStar microfocus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            23448
_diffrn_reflns_theta_full        66.00
_diffrn_reflns_theta_max         69.45
_diffrn_reflns_theta_min         2.76
_exptl_absorpt_coefficient_mu    1.606
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.820
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     692
_refine_ls_number_reflns         6812
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0428P)^2^+0.9651P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0852
_reflns_number_gt                6782
_reflns_number_total             6812
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4011798_si_003.cif
_cod_data_source_block           q06c
_cod_database_code               4028468