Synthesis and Reactivity of 1-Allenyltriazenes.
Jeanbourquin, Loïc N; Scopelliti, Rosario; Fadaei Tirani, Farzaneh; Severin, Kay; Organic letters 19 (2017) 2070–2073; doi:10.1021/acs.orglett.7b00671

data_1545937
_publ_section_title
;
 Synthesis and Reactivity of 1-Allenyltriazenes.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              2070
_journal_page_last               2073
_journal_paper_doi               10.1021/acs.orglett.7b00671
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H23 N3'
_chemical_formula_sum            'C16 H23 N3'
_chemical_formula_weight         257.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2016-11-25 # Formatted by publCIF

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4082(5)
_cell_length_b                   7.7785(3)
_cell_length_c                   19.6994(9)
_cell_measurement_reflns_used    5545
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.1150
_cell_measurement_theta_min      4.4480
_cell_volume                     1594.87(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Mercury 3.9 (CCDC, 2016)'
_computing_publication_material
'CIF Tools (WinGX 2014.1, L.J. Farruggia, 2012)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1333
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -67.00  26.00   1.00    5.00    --  -42.26  37.00   0.00   93
  2  \w   -114.00 -21.00   1.00    5.00    --  -42.26 -37.00-180.00   93
  3  \w   -112.00 -18.00   1.00    5.00    --  -42.26 -57.00  90.00   94
  4  \w      3.00  57.00   1.00    5.00    --   42.26 -99.00  60.00   54
  5  \w     52.00  79.00   1.00    5.00    --   42.26 -99.00 120.00   27
  6  \w     60.00  90.00   1.00    5.00    --   42.26-125.00 -60.00   30
  7  \w    136.00 162.00   1.00   30.00    --  109.26  77.00 -30.00   26
  8  \w     99.00 126.00   1.00   30.00    --  109.26  77.00 -30.00   27
  9  \w     37.00  90.00   1.00   30.00    --  109.26 -61.00 -60.00   53
 10  \w     84.00 178.00   1.00   30.00    --  109.26  30.00 150.00   94
 11  \w     57.00 116.00   1.00   30.00    --  109.26-111.00  60.00   59
 12  \w     40.00 138.00   1.00   30.00    --  109.26 -61.00-180.00   98
 13  \w     33.00 122.00   1.00   30.00    --  109.26 -30.00 -30.00   89
 14  \w     40.00 136.00   1.00   30.00    --  109.26 -61.00  60.00   96
 15  \w     79.00 114.00   1.00   30.00    --  109.26-111.00 -60.00   35
 16  \w     78.00 114.00   1.00   30.00    --  109.26-111.00-180.00   36
 17  \w     33.00 156.00   1.00   30.00    --  109.26 -15.00 150.00  123
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10238
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.317
_diffrn_reflns_theta_min         4.489
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.495
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.447
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.239
_refine_diff_density_max         0.095
_refine_diff_density_min         -0.084
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details
;
 Flack x determined using 1286 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0318P)^2^+0.0866P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0743
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.919
_reflns_number_gt                2921
_reflns_number_total             3152
_reflns_threshold_expression     'I > 2\s(I)'
_publcif_datablock.id            {751d6b01-a9d7-45b2-947a-c622e7b9566d}
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_cod_data_source_file            ol7b00671_si_003.cif
_cod_data_source_block           shelx
_cod_database_code               1545937
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.809
_shelx_estimated_absorpt_t_max   0.891
_shelx_res_checksum              80636
_shelx_hkl_checksum              15183