MeOTf-Mediated Annulation of Alkylnitriles and Arylalkynes Leading to Polysubstituted NH-Pyrroles.
Liu, Yu; Yi, Xiangli; Luo, Xuewei; Xi, Chanjuan; The Journal of organic chemistry 82 (2017) 11391–11398; doi:10.1021/acs.joc.7b01845

data_4033020
_publ_section_title
;
 MeOTf-Mediated Annulation of Alkylnitriles and Arylalkynes Leading to
 Polysubstituted NH-Pyrroles.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11391
_journal_page_last               11398
_journal_paper_doi               10.1021/acs.joc.7b01845
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C20 H18 Cl N O'
_chemical_formula_sum            'C20 H18 Cl N O'
_chemical_formula_weight         323.80
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                85.20(3)
_cell_angle_beta                 78.12(3)
_cell_angle_gamma                89.03(3)
_cell_formula_units_Z            2
_cell_length_a                   7.6298(15)
_cell_length_b                   8.2139(16)
_cell_length_c                   13.786(3)
_cell_measurement_reflns_used    2765
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4817
_cell_measurement_theta_min      1.5146
_cell_volume                     842.5(3)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
????
;
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 270.0000
                 XTD: 44.9276
              2theta: -19.9373
scan:
    Number of images: 360
               Slice: -110.0000 - 70.0000
         Image width: 0.5000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 44.9276
              2theta: -19.9373
scan:
    Number of images: 302
               Slice: -110.0000 - 41.0000
         Image width: 0.5000
            Exp time: 3.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 44.9276
              2theta: -19.9373
;
_diffrn_measurement_device
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.1161
_diffrn_orient_matrix_UB_12      0.0582
_diffrn_orient_matrix_UB_13      0.0327
_diffrn_orient_matrix_UB_21      0.0604
_diffrn_orient_matrix_UB_22      0.0989
_diffrn_orient_matrix_UB_23      0.0387
_diffrn_orient_matrix_UB_31      0.0059
_diffrn_orient_matrix_UB_32      0.0171
_diffrn_orient_matrix_UB_33      -0.0721
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9171
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         2.728
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6029
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.798
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.494
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3780
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0519
_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^)+(0.0740P)^2^+0.3880P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1474
_refine_ls_wR_factor_ref         0.1505
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3536
_reflns_number_total             3780
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01845_si_003.cif
_cod_data_source_block           a
_cod_depositor_comments
'Adding full bibliography for 4033019--4033020.cif.'
_cod_database_code               4033020
_diffrn_number_total             3780
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C13(H13), C20(H20), C17(H17), C9(H9), C19(H19), C12(H12), C10(H10),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C14(H14A,H14B,H14C), C7(H7A,H7B,H7C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'