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_1517915
_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         'C13 H12 Br N3 O'
_chemical_formula_sum            'C13 H12 Br N3 O'
_chemical_formula_weight         306.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-04-24
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Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
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_cell_angle_alpha                90
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_cell_length_a                   8.6857(4)
_cell_length_b                   5.5312(3)
_cell_length_c                   26.9976(15)
_cell_measurement_reflns_used    2384
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.2200
_cell_measurement_theta_min      3.7510
_cell_volume                     1291.74(12)
_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)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0356
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0563143000
_diffrn_orient_matrix_UB_12      -0.0103738000
_diffrn_orient_matrix_UB_13      0.0173338000
_diffrn_orient_matrix_UB_21      -0.0589554000
_diffrn_orient_matrix_UB_22      -0.0088635000
_diffrn_orient_matrix_UB_23      -0.0198849000
_diffrn_orient_matrix_UB_31      0.0086923000
_diffrn_orient_matrix_UB_32      -0.1275254000
_diffrn_orient_matrix_UB_33      -0.0000326000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            14749
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.946
_diffrn_reflns_theta_min         3.030
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.173
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41345
_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    1.574
_exptl_crystal_description
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_exptl_crystal_F_000             616
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_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3162
_refine_ls_number_restraints     0
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_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
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 w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.2097P]
 where P=(Fo^2^+2Fc^2^)/3
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_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
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_reflns_number_gt                1634
_reflns_number_total             3162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol502437y_si_001.cif
_cod_data_source_block           exp_8107
_cod_original_cell_volume        1291.75(12)
_cod_database_code               1517915
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_chemical_oxdiff_formula         'C N O H'
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_olex2_refinement_description
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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:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C13(H13), C6(H6), C10(H10), C3(H3), C9(H9), C12(H12)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;