Taming chlorine azide: access to 1,2-azidochlorides from alkenes.
Valiulin, Roman A.; Mamidyala, Sreeman; Finn, M. G.; The Journal of organic chemistry 80 (2015) 2740–2755; doi:10.1021/acs.joc.5b00009

data_4030727
_publ_section_title
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 Taming chlorine azide: access to 1,2-azidochlorides from alkenes.
;
_journal_issue                   5
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2740
_journal_page_last               2755
_journal_paper_doi               10.1021/acs.joc.5b00009
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C16 H16 Cl N3 O4'
_chemical_formula_sum            'C16 H16 Cl N3 O4'
_chemical_formula_weight         349.77
_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'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-01-27
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_cell_angle_alpha                116.439(2)
_cell_angle_beta                 93.526(3)
_cell_angle_gamma                110.517(2)
_cell_formula_units_Z            2
_cell_length_a                   8.9484(19)
_cell_length_b                   10.234(2)
_cell_length_c                   11.213(2)
_cell_measurement_reflns_used    3575
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.605
_cell_measurement_theta_min      2.299
_cell_volume                     831.7(3)
_computing_cell_refinement       'SAINT v8.32B (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.32B (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II'
_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  0.0327
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13534
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.037
_diffrn_reflns_theta_min         2.100
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0608 before and 0.0390 after correction.
The Ratio of minimum to maximum transmission is 0.9296.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of DCM, hexanes and ethanol'
_exptl_crystal_size_max          0.626
_exptl_crystal_size_mid          0.557
_exptl_crystal_size_min          0.324
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5242
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.3437P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1429
_refine_ls_wR_factor_ref         0.1714
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2990
_reflns_number_total             5242
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00009_si_005.cif
_cod_data_source_block           mgrav3052
_cod_depositor_comments          'Adding full bibliography for 4030727.cif.'
_cod_original_cell_volume        831.6(3)
_cod_database_code               4030727
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.922
_shelx_estimated_absorpt_t_min   0.857
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C16-H16B
 0.995 with sigma of 0.02
 C9-H9
 0.985 with sigma of 0.02
 C3-H3
 0.999 with sigma of 0.02
 C5-H5A = C5-H5B
 0.985 with sigma of 0.02
 C6-H6A = C6-H6B
 0.985 with sigma of 0.02
 C16-H16B \\sim C16-H16C \\sim C16-H16A
 with sigma of 0.005
 H16C-H16B \\sim H16C-H16A \\sim H16B-H16A
 with sigma of 0.005
 C12-H12 \\sim C11-H11 \\sim C10-H10 \\sim C9-H9
 with sigma of 0.005
 C5-H5A \\sim C5-H5B
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uiso(H16A) = Uiso(H16B) = Uiso(H16C)
Uiso(H9) = Uiso(H10) = Uiso(H11) = Uiso(H12)
4.a Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;