Cyclopropeniminium Ions Exhibit Unique Reactivity Profiles with Bioorthogonal Phosphines.
Heiss, Tyler K.; Prescher, Jennifer A.; The Journal of organic chemistry 84 (2019) 7443–7448; doi:10.1021/acs.joc.9b00518

data_4034634
_publ_section_title
;
 Cyclopropeniminium Ions Exhibit Unique Reactivity Profiles with
 Bioorthogonal Phosphines.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7443
_journal_page_last               7448
_journal_paper_doi               10.1021/acs.joc.9b00518
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C29 H35 B F4 N P S'
_chemical_formula_weight         547.42
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                77.916(2)
_cell_angle_beta                 79.1443(19)
_cell_angle_gamma                89.242(2)
_cell_formula_units_Z            2
_cell_length_a                   9.3487(15)
_cell_length_b                   10.2759(16)
_cell_length_c                   14.892(2)
_cell_measurement_reflns_used    8706
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.84
_cell_measurement_theta_min      2.22
_cell_volume                     1373.4(4)
_computing_cell_refinement       'Bruker SAINT 8.34a, 2013'
_computing_data_collection       'Bruker APEX2 2014.11-0, 2014'
_computing_data_reduction        'Bruker SAINT 8.34a, 2013'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL 2014/4'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15421
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         28.841
_diffrn_reflns_theta_min         1.424
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.8015
_exptl_absorpt_correction_T_min  0.6943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS 2014/5'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    not_measured
_exptl_crystal_description       irregular
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.367
_exptl_crystal_size_mid          0.255
_exptl_crystal_size_min          0.227
_refine_diff_density_max         1.002
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     474
_refine_ls_number_reflns         6528
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0465
_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^)+(0.0598P)^2^+1.3602P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1175
_refine_ls_wR_factor_ref         0.1232
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5560
_reflns_number_total             6528
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b00518_si_002.cif
_cod_data_source_block           jap1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not_measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1373.3(4)
_cod_database_code               4034634
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.951
_exptl_absorpt_special_details
; 
Reflections not merged 
15421 Corrected reflections written to file jap1s.hkl 
Estimated minimum and maximum transmission:  0.6943  0.8015 
The ratio (0.8663A) of these values is more reliable than their absolute values 
Additional spherical absorption correction applied with mu*r =  0.1500 
Lambda/2 correction factor = 0.00150 
;
_shelx_res_checksum              27815
_shelx_hkl_checksum              32078