Highly N2-selective allylation of NH-1,2,3-triazoles with allenamides mediated by N-iodosuccinimide
Re He Man, Xi Jia Ai Ti; Liu, Yong Chun; Li, Xiao Xiao; Zhao, Zhi Gang; New Journal of Chemistry 43 (2019) 14739–; doi:10.1039/C9NJ03014J

data_7058767
_publ_section_title
;
 Highly N2-selective allylation of NH-1,2,3-triazoles with allenamides
 mediated by N-iodosuccinimide
;
_journal_issue                   37
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14739
_journal_paper_doi               10.1039/C9NJ03014J
_journal_volume                  43
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C26 H24 F I N4 O2 S'
_chemical_formula_sum            'C26 H24 F I N4 O2 S'
_chemical_formula_weight         602.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-11 deposited with the CCDC.    2019-08-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6016(4)
_cell_length_b                   24.2609(6)
_cell_length_c                   6.07906(11)
_cell_measurement_reflns_used    3534
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.4600
_cell_measurement_theta_min      6.0780
_cell_volume                     2448.46(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega  -31.00   53.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000   30.0000 84

  2 omega   10.00  104.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   77.0000   60.0000 94

  3 omega   20.00  104.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000  -60.0000 84

  4 omega   57.00   94.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 37

  5 omega   23.00   90.00   1.0000    1.4000
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000 -180.0000 67

  6 omega   57.00  150.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 93

  7 omega  117.00  149.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 32

  8 omega   90.00  177.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000 -120.0000 87

  9 omega   71.00  109.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -150.0000 38

 10 omega   46.00  120.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000   90.0000 74

 11 omega   48.00   74.00   1.0000    5.5900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0878534000
_diffrn_orient_matrix_UB_12      -0.0201753000
_diffrn_orient_matrix_UB_13      -0.0141549000
_diffrn_orient_matrix_UB_21      -0.0298182000
_diffrn_orient_matrix_UB_22      0.0598794000
_diffrn_orient_matrix_UB_23      0.0208108000
_diffrn_orient_matrix_UB_31      0.0024176000
_diffrn_orient_matrix_UB_32      0.0060537000
_diffrn_orient_matrix_UB_33      -0.2522354000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7874
_diffrn_reflns_point_group_measured_fraction_full 0.758
_diffrn_reflns_point_group_measured_fraction_max 0.732
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.618
_diffrn_reflns_theta_min         5.329
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.406
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_description       needle
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.587
_refine_diff_density_min         -1.247
_refine_diff_density_rms         0.166
_refine_ls_abs_structure_details
;
 Flack x determined using 855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.021(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3571
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0575
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1226P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1498
_refine_ls_wR_factor_ref         0.1522
_reflns_Friedel_coverage         0.367
_reflns_Friedel_fraction_full    0.466
_reflns_Friedel_fraction_max     0.437
_reflns_number_gt                3432
_reflns_number_total             3571
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9nj03014j2.cif
_cod_data_source_block           lxx-190305-150k
_cod_depositor_comments          'Adding full bibliography for 7058767.cif.'
_cod_original_cell_volume        2448.47(10)
_cod_database_code               7058767
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.30
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C5(H5), C1(H1), C12(H12), C16(H16), C4(H4), C2(H2), C15(H15),
 C13(H13), C22(H22), C25(H25), C24(H24), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              52799
_olex2_submission_special_instructions 'No special instructions were received'