Cyclopentadiene-Phosphine/Palladium-Catalyzed Synthesis of Indolizines from Pyrrole and 1,4-Dibromo-1,3-butadienes.
Hao, Wei; Wang, Han; Ye, Qingyu; Zhang, Wen-Xiong; Xi, Zhenfeng; Organic letters 17 (2015) 5674–5677; doi:10.1021/acs.orglett.5b02959

data_1540598
_publ_section_title
;
 Cyclopentadiene-Phosphine/Palladium-Catalyzed Synthesis of Indolizines
 from Pyrrole and 1,4-Dibromo-1,3-butadienes.
;
_journal_issue                   22
_journal_name_full               'Organic letters'
_journal_page_first              5674
_journal_page_last               5677
_journal_paper_doi               10.1021/acs.orglett.5b02959
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C21 H21 N Si'
_chemical_formula_sum            'C21 H21 N Si'
_chemical_formula_weight         315.48
_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             2015-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                95.235(5)
_cell_angle_beta                 105.120(5)
_cell_angle_gamma                108.782(5)
_cell_formula_units_Z            4
_cell_length_a                   10.2204(5)
_cell_length_b                   10.3756(7)
_cell_length_c                   18.4485(12)
_cell_measurement_reflns_used    3753
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      27.0190
_cell_measurement_theta_min      3.1820
_cell_volume                     1754.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -68.00   35.00   1.0000    3.0400
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -77.0000   30.0000 103

  2 omega   -6.00   81.00   1.0000    3.0400
omega____ theta____ kappa____ phi______ frames
    -       10.7017   57.0000  150.0000 87

  3 omega  -74.00   22.00   1.0000    3.0400
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -77.0000 -120.0000 96

  4 omega  -19.00    6.00   1.0000    3.0400
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -99.0000  150.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0080603000
_diffrn_orient_matrix_UB_12      -0.0422372000
_diffrn_orient_matrix_UB_13      0.0278675000
_diffrn_orient_matrix_UB_21      -0.0739141000
_diffrn_orient_matrix_UB_22      -0.0361409000
_diffrn_orient_matrix_UB_23      -0.0215584000
_diffrn_orient_matrix_UB_31      0.0201900000
_diffrn_orient_matrix_UB_32      -0.0481948000
_diffrn_orient_matrix_UB_33      -0.0201320000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13052
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.800
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic yellowish white'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6896
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0662
_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^)+(0.0556P)^2^+1.4132P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1487
_refine_ls_wR_factor_ref         0.1689
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4804
_reflns_number_total             6896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b02959_si_002.cif
_cod_data_source_block           2g
_cod_database_code               1540598
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C21 H21 N1 Si1'
_shelx_estimated_absorpt_t_max   0.987
_shelx_estimated_absorpt_t_min   0.987
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C32, C31, C33
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C41)
\\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(C40) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C27(H27), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39)
4.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C40(H40A,H40B,
 H40C), C41(H41A,H41B,H41C), C42(H42A,H42B,H42C)
;
_olex2_date_sample_data_collection 2015-06-11
_olex2_submission_special_instructions 'No special instructions were received'