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_7123271
_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         'C26 H23 N O2, C H2 Cl2'
_chemical_formula_sum            'C27 H25 Cl2 N O2'
_chemical_formula_weight         466.38
_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
_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                 91.871(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3898(6)
_cell_length_b                   14.8000(9)
_cell_length_c                   18.8914(12)
_cell_measurement_reflns_used    9836
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      35.93
_cell_measurement_theta_min      2.43
_cell_volume                     2344.5(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 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0468
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            102888
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         36.436
_diffrn_reflns_theta_min         2.429
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.9677
_exptl_absorpt_correction_T_min  0.9178
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'apex3 BRUKER'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.956
_refine_diff_density_min         -0.933
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         11417
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0534P)^2^+1.3625P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1332
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8149
_reflns_number_total             11417
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc01197h2.cif
_cod_data_source_block           10
_cod_database_code               7123271
_shelx_estimated_absorpt_t_min   0.960
_shelx_estimated_absorpt_t_max   0.968
_shelx_res_checksum              16183
_shelx_hkl_checksum              54322