Stereoselective Synthesis of Oxabicyclo[2.2.1]heptenes via a Tandem Dirhodium(II)-Catalyzed Triazole Denitrogenation and [3 + 2] Cycloaddition.
Yuan, Hao; Gong, Jianxian; Yang, Zhen; Organic letters 18 (2016) 5500–5503; doi:10.1021/acs.orglett.6b02703

data_1555855
_publ_section_title
;
 Stereoselective Synthesis of Oxabicyclo[2.2.1]heptenes via a Tandem
 Dirhodium(II)-Catalyzed Triazole Denitrogenation and [3 + 2]
 Cycloaddition.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5500
_journal_page_last               5503
_journal_paper_doi               10.1021/acs.orglett.6b02703
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C21 H23 N O3 S'
_chemical_formula_weight         369.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 93.165(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.264(3)
_cell_length_b                   17.364(5)
_cell_length_c                   21.635(7)
_cell_measurement_reflns_used    3758
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      22.8
_cell_volume                     3850(2)
_computing_cell_refinement       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.1275
_diffrn_reflns_av_unetI/netI     0.0747
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            29958
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         68.308
_diffrn_reflns_theta_min         3.265
_exptl_absorpt_coefficient_mu    1.654
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0029(6)
_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   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     470
_refine_ls_number_reflns         6880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.176
_refine_ls_R_factor_all          0.1310
_refine_ls_R_factor_gt           0.0915
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2809
_refine_ls_wR_factor_ref         0.3499
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4392
_reflns_number_total             6880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02703_si_003.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1555855
_shelxl_version_number           2014-3
_shelx_res_checksum              21203
_shelx_hkl_checksum              22934