Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins.
Li, Hongze; Shen, Shou-Jie; Zhu, Cheng-Liang; Xu, Hao; Journal of the American Chemical Society 141 (2019) 9415–9421; doi:10.1021/jacs.9b04381

data_4128710
_publ_section_title
;
 Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated
 Olefins.
;
_journal_issue                   23
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9415
_journal_page_last               9421
_journal_paper_doi               10.1021/jacs.9b04381
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C16 H22 N2 O4 S'
_chemical_formula_sum            'C16 H22 N2 O4 S'
_chemical_formula_weight         338.41
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-27
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.06.07 svn.r3419 for OlexSys, GUI svn.r5353)
;
_cell_angle_alpha                82.378(3)
_cell_angle_beta                 86.980(3)
_cell_angle_gamma                87.899(3)
_cell_formula_units_Z            2
_cell_length_a                   7.247(2)
_cell_length_b                   10.734(3)
_cell_length_c                   10.837(3)
_cell_measurement_reflns_used    8484
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.44
_cell_measurement_theta_min      2.82
_cell_volume                     834.0(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0229
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13524
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.442
_diffrn_reflns_theta_min         1.898
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0520 before and 0.0393 after correction. The Ratio of minimum to maximum transmission is 0.9261. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.434
_exptl_crystal_size_mid          0.319
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.011
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0882
_refine_ls_R_factor_gt           0.0830
_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^)+(0.1446P)^2^+1.4825P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2466
_refine_ls_wR_factor_ref         0.2523
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2766
_reflns_number_total             3073
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04381_si_002.cif
_cod_data_source_block           hx617a
_cod_database_code               4128710
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.912
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N1(H1)
2.b Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C6(H6)
2.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B)
2.d Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C15(H15), C16(H16)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id HL-5-115
_olex2_submission_special_instructions 'No special instructions were received'