Photooxygenation of 2-Propargylfurans: a Path to Structurally Diverse Nitrogen-Containing 5-Membered Rings
Marin, Lucile; Force, Guillaume; Guillot, Régis; Gandon, Vincent; Schulz, Emmanuelle; Leboeuf, David; Chemical Communications  (2019) –; doi:10.1039/C9CC01197H

data_7123270
_publ_section_title
;
 Photooxygenation of 2-Propargylfurans: a Path to Structurally Diverse
 Nitrogen-Containing 5-Membered Rings
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC01197H
_journal_year                    2019
_chemical_formula_moiety         'C23 H21 N O3'
_chemical_formula_sum            'C23 H21 N O3'
_chemical_formula_weight         359.41
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-01-23 deposited with the CCDC.    2019-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                74.5430(10)
_cell_angle_beta                 70.1210(10)
_cell_angle_gamma                76.3680(10)
_cell_formula_units_Z            2
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_cell_length_b                   10.7510(2)
_cell_length_c                   11.9840(3)
_cell_measurement_reflns_used    9920
_cell_measurement_temperature    100(1)
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_cell_measurement_theta_min      2.42
_cell_volume                     942.88(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
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_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24636
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         36.381
_diffrn_reflns_theta_min         1.846
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS apex2'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         8644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0409
_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^)+(0.0685P)^2^+0.1554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1246
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7160
_reflns_number_total             8644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01197h2.cif
_cod_data_source_block           20
_cod_database_code               7123270
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.991
_shelx_res_checksum              66735
_shelx_hkl_checksum              61243