A formal [3 + 2] annulation reaction of propargyl sulfonium compounds and <i>N</i>-ylides: access to pyrrolo[2,1-<i>a</i>]quinolines, pyrrolo[2,1-<i>a</i>]phthalazines and indolizines.
Zheng, Jing; He, Xiaojie; Xu, Hong; Liu, Hua; Yang, Weiran; Organic & biomolecular chemistry 18 (2020) 8867–8875; doi:10.1039/d0ob01739f

data_7157800
_publ_section_title
;
 A formal [3 + 2] annulation reaction of propargyl sulfonium compounds and
 <i>N</i>-ylides: access to pyrrolo[2,1-<i>a</i>]quinolines,
 pyrrolo[2,1-<i>a</i>]phthalazines and indolizines.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8867
_journal_page_last               8875
_journal_paper_doi               10.1039/d0ob01739f
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C20 H14 Cl N O'
_chemical_formula_weight         319.77
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-08-10 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                75.7790(10)
_cell_angle_beta                 69.4490(10)
_cell_angle_gamma                67.4610(10)
_cell_formula_units_Z            2
_cell_length_a                   8.0991(3)
_cell_length_b                   10.0866(3)
_cell_length_c                   10.5705(3)
_cell_measurement_reflns_used    6263
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      53.86
_cell_measurement_theta_min      3.92
_cell_volume                     740.63(4)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9190
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.902
_diffrn_reflns_theta_min         3.918
_exptl_absorpt_coefficient_mu    1.517
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2690
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0504P)^2^+0.4286P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2418
_reflns_number_total             2690
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob01739f2.cif
_cod_data_source_block           20200702LI_ZNZ5223_2_0m_a
_cod_database_code               7157800
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.839
_shelx_estimated_absorpt_t_max   0.888
_shelx_res_checksum              73489