Synthesis of 2,3-dihydro-1H-pyrroles by intramolecular cyclization of N-(3-butynyl)-sulfonamides.
Chung, Min-Ching; Chan, Yung-Hsiang; Chang, Wen-Jung; Hou, Duen-Ren; Organic & biomolecular chemistry 15 (2017) 3783–3790; doi:10.1039/c7ob00528h

data_7155560
_publ_section_title
;
 Synthesis of 2,3-dihydro-1H-pyrroles by intramolecular cyclization of
 N-(3-butynyl)-sulfonamides.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3783
_journal_page_last               3790
_journal_paper_doi               10.1039/c7ob00528h
_journal_volume                  15
_journal_year                    2017
_chemical_formula_sum            'C21 H25 N O2 S'
_chemical_formula_weight         355.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-12-13 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8441(4)
_cell_length_b                   11.9103(5)
_cell_length_c                   13.4579(5)
_cell_measurement_reflns_used    9893
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.25
_cell_measurement_theta_min      2.29
_cell_volume                     1898.46(12)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'Bruker APEX2 (Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_molecular_graphics    'SHELXS-97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker KAPPA APEX II diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25711
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.408
_diffrn_reflns_theta_min         2.283
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       Block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1087 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.48(2)
_refine_ls_extinction_coef       none
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         25711
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0379
_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^)+(0.0350P)^2^+0.2445P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                20461
_reflns_number_total             25711
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00528h2.cif
_cod_data_source_block           16AU09_0m
_cod_depositor_comments          'Adding full bibliography for 7155560.cif.'
_cod_database_code               7155560
_shelx_estimated_absorpt_t_min   0.947
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-2
_shelx_res_checksum              95798