Direct oxidative coupling of N-acyl pyrroles with alkenes by ruthenium(ii)-catalyzed regioselective C2-alkenylation.
Chen, Weiqiang; Li, Hui-Jing; Li, Qin-Ying; Wu, Yan-Chao; Organic & biomolecular chemistry 18 (2020) 500–513; doi:10.1039/c9ob02421b

data_7157296
_publ_section_title
;
 Direct oxidative coupling of N-acyl pyrroles with alkenes by
 ruthenium(ii)-catalyzed regioselective C2-alkenylation.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              500
_journal_page_last               513
_journal_paper_doi               10.1039/c9ob02421b
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C17 H17 N O4'
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-09 deposited with the CCDC.	2019-12-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.662(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2856(5)
_cell_length_b                   13.4694(6)
_cell_length_c                   11.2174(5)
_cell_measurement_reflns_used    2543
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3630
_cell_measurement_theta_min      5.1310
_cell_volume                     1553.96(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     20.00  55.00   1.00    1.00    --    0.00  57.00-120.00   35
  2  \w    -21.00  24.00   1.00    1.00    --    0.00  57.00-180.00   45
  3  \w    -39.00 -14.00   1.00    1.00    --    0.00 128.00  67.00   25
  4  \w    -11.00  65.00   1.00    1.00    --   54.00 -57.00 120.00   76
  5  \w     33.00 111.00   1.00    1.00    --   54.00-125.00  30.00   78
  6  \w     62.00 108.00   1.00    1.00    --   54.00  57.00 -60.00   46
  7  \w     27.00 108.00   1.00    1.00    --   54.00  37.00 -90.00   81
  8  \w     53.00  78.00   1.00    1.00    --  108.00 -37.00  60.00   25
  9  \w     81.00 107.00   1.00    1.00    --  108.00-111.00 -90.00   26
 10  \w     36.00 112.00   1.00    1.00    --  108.00-111.00  60.00   76
 11  \w    100.00 171.00   1.00    1.00    --  108.00 111.00  60.00   71
 12  \w    103.00 128.00   1.00    1.00    --  108.00 111.00-180.00   25
 13  \w     88.00 127.00   1.00    1.00    --  108.00 -37.00  60.00   39
 14  \w    108.00 148.00   1.00    1.00    --  108.00 111.00 -90.00   40
 15  \w     81.00 177.00   1.00    1.00    --  108.00  37.00-120.00   96
 16  \w    112.00 166.00   1.00    1.00    --  108.00 111.00 120.00   54
 17  \w     66.00 140.00   1.00    1.00    --  108.00 -77.00  60.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0561952000
_diffrn_orient_matrix_UB_12      0.0991285000
_diffrn_orient_matrix_UB_13      0.0445004000
_diffrn_orient_matrix_UB_21      0.0872735000
_diffrn_orient_matrix_UB_22      0.0567664000
_diffrn_orient_matrix_UB_23      -0.0875056000
_diffrn_orient_matrix_UB_31      -0.1080406000
_diffrn_orient_matrix_UB_32      -0.0057735000
_diffrn_orient_matrix_UB_33      -0.0960011000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5677
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.080
_diffrn_reflns_theta_max         67.080
_diffrn_reflns_theta_min         5.131
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2779
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0626P)^2^+0.1784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1066
_refine_ls_wR_factor_ref         0.1170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2303
_reflns_number_total             2779
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ob02421b2.cif
_cod_data_source_block           zx-190331
_cod_depositor_comments          'Adding full bibliography for 7157296.cif.'
_cod_original_cell_volume        1553.98(12)
_cod_database_code               7157296
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHON
_chemical_oxdiff_usercomment     'C H O N'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C8(H8), C2(H2), C10(H10), C6(H6), C9(H9), C3(H3), C5(H5),
 C4(H4)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              69350
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.505
_oxdiff_exptl_absorpt_empirical_full_min 0.771