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_7123269
_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_absolute_configuration ad
_chemical_formula_moiety         'C19 H17 N O2'
_chemical_formula_sum            'C19 H17 N O2'
_chemical_formula_weight         291.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_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                90
_cell_angle_beta                 107.380(16)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.358(2)
_cell_length_b                   5.3966(14)
_cell_length_c                   15.126(3)
_cell_measurement_reflns_used    4032
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      66.81
_cell_measurement_theta_min      3.06
_cell_volume                     729.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_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 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_unetI/netI     0.0739
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            8823
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        66.928
_diffrn_reflns_theta_max         66.928
_diffrn_reflns_theta_min         3.061
_exptl_absorpt_coefficient_mu    0.686
_exptl_absorpt_correction_T_max  0.9901
_exptl_absorpt_correction_T_min  0.9681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'apex3 Bruker'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2488
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0501
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0254P)^2^+0.3502P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1077
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.915
_reflns_Friedel_fraction_max     0.915
_reflns_number_gt                2081
_reflns_number_total             2488
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01197h2.cif
_cod_data_source_block           3aa
_cod_database_code               7123269
_shelx_estimated_absorpt_t_min   0.863
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              81511
_shelx_hkl_checksum              62260