Direct Synthesis of Butadiynyl-Substituted Pyrroles under Solvent- and Transition Metal-Free Conditions. The First Formal Inverse Sonogashira Coupling for 1-Halobutadiynes
Tomilin, Denis; Pigulski, Bartłomiej; Gulia, Nurbey; Arendt, Agata; Sobenina, Luybov; Mikhaleva, Al'bina; Szafert, Slawomir; Trofimov, Boris; RSC Adv.  (2015) –; doi:10.1039/C5RA08820H

data_7221814
_publ_section_title
;
 Direct Synthesis of Butadiynyl-Substituted Pyrroles under Solvent- and
 Transition Metal-Free Conditions. The First Formal Inverse Sonogashira
 Coupling for 1-Halobutadiynes
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA08820H
_journal_year                    2015
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.30
_chemical_name_systematic
;
Ethyl 5-(1-methyl-4,5,6,7-tetrahydro-1H-indol-2-yl)penta-2,4-diynoate
;
_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-2013
_audit_update_record
;
2014-12-05 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                106.45(4)
_cell_angle_beta                 104.02(3)
_cell_angle_gamma                103.26(3)
_cell_formula_units_Z            2
_cell_length_a                   7.685(2)
_cell_length_b                   9.000(3)
_cell_length_c                   11.089(4)
_cell_measurement_reflns_used    3727
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.4787
_cell_measurement_theta_min      2.8781
_cell_volume                     676.1(5)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.650
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.650
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6145
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.650
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         32.552
_diffrn_reflns_theta_min         2.884
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2/hexane'
_exptl_crystal_size_max          0.990
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0519
_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^)+(0.0996P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1401
_refine_ls_wR_factor_ref         0.1474
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2525
_reflns_number_total             3201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra08820h2.cif
_cod_data_source_block           tom3abs
_cod_original_cell_volume        676.1(4)
_cod_database_code               7221814
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-4
_shelx_res_checksum              99231