Reactions of α-haloacroleins with azides: highly regioselective synthesis of formyl triazoles
Zhang, Dongsheng; Fan, Yingzhu; Yan, Zhongliang; Nie, Yi; Xiong, Xingquan; Gao, Lizhu; Green Chemistry 21 (2019) 4211–; doi:10.1039/C9GC01129C

data_7233071
_publ_section_title
;
 Reactions of \a-haloacroleins with azides: highly regioselective
 synthesis of formyl triazoles
;
_journal_issue                   15
_journal_name_full               'Green Chemistry'
_journal_page_first              4211
_journal_paper_doi               10.1039/C9GC01129C
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C10 H9 N3 O'
_chemical_formula_sum            'C10 H9 N3 O'
_chemical_formula_weight         187.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-08-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2018-08-27 deposited with the CCDC.    2019-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.5391(9)
_cell_length_b                   9.1500(14)
_cell_length_c                   19.861(2)
_cell_measurement_reflns_used    2890
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.8370
_cell_measurement_theta_min      3.8520
_cell_volume                     1915.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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      173.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -45.00  83.00   1.00    5.00    --   15.49   0.00 -30.00  128
  2  \w    -11.00  14.00   1.00    5.00    --  -16.28 -99.00 -90.00   25
  3  \w    -50.00  32.00   1.00    5.00    --   15.49 -38.00 -60.00   82
  4  \w    -24.00  21.00   1.00    5.00    --  -16.28 -99.00  90.00   45
  5  \w    -71.00 -33.00   1.00    5.00    --  -16.28 131.00 169.00   38
  6  \w    -62.00 -37.00   1.00    5.00    --  -16.28 138.00 -15.00   25
  7  \w     44.00  70.00   1.00    5.00    --   15.49 178.00-120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0064232000
_diffrn_orient_matrix_UB_12      -0.0550488000
_diffrn_orient_matrix_UB_13      -0.0249390000
_diffrn_orient_matrix_UB_21      0.0041287000
_diffrn_orient_matrix_UB_22      -0.0539134000
_diffrn_orient_matrix_UB_23      0.0255732000
_diffrn_orient_matrix_UB_31      -0.0668232000
_diffrn_orient_matrix_UB_32      -0.0086111000
_diffrn_orient_matrix_UB_33      -0.0008222000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12309
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.59
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.683
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1687
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.683
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1630P)^2^+1.2900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1410
_refine_ls_wR_factor_ref         0.1777
_reflns_number_gt                1281
_reflns_number_total             1687
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9gc01129c2.cif
_cod_data_source_block           exp_5228
_cod_depositor_comments          'Adding full bibliography for 7233071.cif.'
_cod_database_code               7233071
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C10(H10), C9(H9), C8(H8), C7(H7), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.521
_oxdiff_exptl_absorpt_empirical_full_min 0.470