Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.
Porter, Matthew R.; Shaker, Rami M.; Calcanas, Cristian; Topczewski, Joseph J.; Journal of the American Chemical Society  (2018) –; doi:10.1021/jacs.7b11299

data_4127024
_publ_section_title
;
 Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of
 Tetralins, Chromanes, and Tetrahydroquinolines.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b11299
_journal_year                    2018
_chemical_formula_moiety         'C13 H14 Br N3'
_chemical_formula_sum            'C13 H14 Br N3'
_chemical_formula_weight         292.18
_chemical_name_common            MRP2046
_chemical_name_systematic        MRP2046
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
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_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                104.663(2)
_cell_angle_beta                 94.770(2)
_cell_angle_gamma                91.695(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4813(14)
_cell_length_b                   8.7430(16)
_cell_length_c                   9.9454(18)
_cell_measurement_reflns_used    3489
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.74
_cell_volume                     626.3(2)
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_collection       'APEX II, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_molecular_graphics    'Shelxle-(Rev. 825)(Huebschle, C. B., 2011)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker 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  0.0263
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
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_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7268
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.431
_diffrn_reflns_theta_min         2.126
_diffrn_source                   normal
_exptl_absorpt_coefficient_mu    3.263
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_description       Plates
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.232
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_exptl_transmission_factor_max   0.7455
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_refine_diff_density_max         0.370
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0295P)^2^+0.1053P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0607
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2458
_reflns_number_total             2817
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b11299_si_002.cif
_cod_data_source_block           17079_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4127024
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              22190
_shelx_hkl_checksum              56006