Late Stage Azidation of Complex Molecules.
Karimov, Rashad R.; Sharma, Ankit; Hartwig, John F.; ACS central science 2 (2016) 715–724; doi:10.1021/acscentsci.6b00214

data_4516770
_publ_section_title
;
 Late Stage Azidation of Complex Molecules.
;
_journal_issue                   10
_journal_name_full               'ACS central science'
_journal_page_first              715
_journal_page_last               724
_journal_paper_doi               10.1021/acscentsci.6b00214
_journal_volume                  2
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H23 N3 O3'
_chemical_formula_weight         293.36
_chemical_name_common            azide_3f
_chemical_name_systematic        azide_3f
_space_group.centring_type       primitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.773(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1594(5)
_cell_length_b                   6.5226(3)
_cell_length_c                   11.7589(5)
_cell_measurement_reflns_used    6295
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      68.07
_cell_measurement_theta_min      3.83
_cell_volume                     765.48(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP-32
_computing_publication_material  WinGX
_computing_structure_refinement  SHELXL-2014
_computing_structure_solution    SHELXT-2014
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_refln_scan_rate          2
_diffrn_refln_scan_width         2.0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12040
_diffrn_reflns_point_group_measured_fraction_full 0.923
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         68.341
_diffrn_reflns_theta_min         3.826
_diffrn_source                   'microfocus rotating anode'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  0.929
_exptl_absorpt_correction_T_min  0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_description       plate
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
; 
 Flack x determined using 800 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2578
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0616P)^2^+0.1644P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.689
_reflns_Friedel_fraction_full    0.834
_reflns_Friedel_fraction_max     0.829
_reflns_number_gt                2215
_reflns_number_total             2578
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            oc6b00214_si_002.cif
_cod_data_source_block           azide3f
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4516770
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_checksum              28116
_shelx_hkl_checksum              3285