Conversion of 2-Furylcarbinols with Alkyl or Aryl Azides to Highly Functionalized 1,2,3-Triazoles via Cascade Formal [3 + 2] Cycloaddition/Ring-Opening.
Guo, Jiawei; Yu, Binxun; Wang, Ya-Nan; Duan, Dongyu; Ren, Li-Li; Gao, Ziwei; Gou, Jing; Organic letters 16 (2014) 5088–5091; doi:10.1021/ol502437y

data_1517916
_publ_section_title
;
 Conversion of 2-Furylcarbinols with Alkyl or Aryl Azides to Highly
 Functionalized 1,2,3-Triazoles via Cascade Formal [3 + 2]
 Cycloaddition/Ring-Opening.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5088
_journal_page_last               5091
_journal_paper_doi               10.1021/ol502437y
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C9 H13 N3 O'
_chemical_formula_sum            'C9 H13 N3 O'
_chemical_formula_weight         179.22
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3'
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_atom_sites_solution_hydrogens   geom
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Olex2 1.2
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_cell_length_c                   5.4546(5)
_cell_measurement_reflns_used    1991
_cell_measurement_temperature    293(2)
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_cell_measurement_theta_min      4.2340
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_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_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
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
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_diffrn_ambient_temperature      293(2)
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_diffrn_measured_fraction_theta_full 0.998
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_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0224485000
_diffrn_orient_matrix_UB_12      0.0229514000
_diffrn_orient_matrix_UB_13      0.0112161000
_diffrn_orient_matrix_UB_21      0.0133465000
_diffrn_orient_matrix_UB_22      -0.0128695000
_diffrn_orient_matrix_UB_23      0.0123277000
_diffrn_orient_matrix_UB_31      0.0032459000
_diffrn_orient_matrix_UB_32      0.0007945000
_diffrn_orient_matrix_UB_33      -0.1289669000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -41
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_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11226
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.973
_diffrn_reflns_theta_min         3.465
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour
;
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_exptl_crystal_density_diffrn    1.171
_exptl_crystal_description
;
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_exptl_crystal_F_000             1728
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0005(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0667
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0788P)^2^+3.6075P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1416
_reflns_number_total             2443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502437y_si_002.cif
_cod_data_source_block           exp_8488
_cod_original_cell_volume        4573.0(10)
_cod_database_code               1517916
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_chemical_oxdiff_formula         'C H N O'
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_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 Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8B,H8A)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C)
;
_shelx_res_checksum              84338
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