Synthesis of homopropargylamines from 2-cyanoazetidines.
Quinodoz, P.; Wright, K.; Drouillat, B.; David, O.; Marrot, J.; Couty, F.; Chemical communications (Cambridge, England) 52 (2016) 10072–10075; doi:10.1039/c6cc05713f

data_7124930
_publ_section_title
;
 Synthesis of homopropargylamines from 2-cyanoazetidines.
;
_journal_issue                   65
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              10072
_journal_page_last               10075
_journal_paper_doi               10.1039/c6cc05713f
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C29 H33 N3 O2'
_chemical_formula_weight         455.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-02-11 deposited with the CCDC.
2016-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                87.115(2)
_cell_angle_beta                 71.784(2)
_cell_angle_gamma                82.973(2)
_cell_formula_units_Z            2
_cell_length_a                   9.6437(4)
_cell_length_b                   11.6855(5)
_cell_length_c                   12.1217(6)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.53
_cell_measurement_theta_min      2.38
_cell_volume                     1287.70(10)
_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  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            73096
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.069
_diffrn_reflns_theta_min         2.385
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2014/5)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_transmission_factor_max   0.7460
_exptl_transmission_factor_min   0.7007
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.184
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     314
_refine_ls_number_reflns         7537
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0511
_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^)+(0.1056P)^2^+0.1933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1632
_refine_ls_wR_factor_ref         0.1960
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5739
_reflns_number_total             7537
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc05713f2.cif
_cod_data_source_block           pq255_a
_cod_database_code               7124930
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.991
_exptl_absorpt_special_details   'Blessing, Acta Cryst. (1995) A51, 33-38'
_shelx_res_checksum              40492
_shelx_hkl_checksum              36954