Formation of Cyclopenta[c]pyridine Derivatives from 2,5-Disubstituted Pyrroles and 1,4-Dibromo-1,3-butadienes via Pyrrole-Ring One-Carbon Expansion.
Yin, Jianhao; Ye, Qingyu; Hao, Wei; Du, Shuaijing; Gu, Yucheng; Zhang, Wen-Xiong; Xi, Zhenfeng; Organic letters 19 (2017) 138–141; doi:10.1021/acs.orglett.6b03431

data_1544948
_publ_section_title
;
 Formation of Cyclopenta[c]pyridine Derivatives from 2,5-Disubstituted
 Pyrroles and 1,4-Dibromo-1,3-butadienes via Pyrrole-Ring One-Carbon
 Expansion.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              138
_journal_page_last               141
_journal_paper_doi               10.1021/acs.orglett.6b03431
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C28 H29 N'
_chemical_formula_sum            'C28 H29 N'
_chemical_formula_weight         379.52
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-10-22
_audit_creation_method
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Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
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_cell_angle_alpha                90.00
_cell_angle_beta                 102.139(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.7589(12)
_cell_length_b                   10.4662(8)
_cell_length_c                   26.8462(16)
_cell_measurement_reflns_used    5229
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      27.2880
_cell_measurement_theta_min      3.4940
_cell_volume                     4328.9(5)
_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
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
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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, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega   38.00   85.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   77.0000   30.0000 47

  2 omega  -62.00   -1.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -57.0000   30.0000 61

  3 omega   45.00   72.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017 -178.0000   30.0000 27

  4 omega   61.00   99.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017 -178.0000   60.0000 38

  5 omega  -85.00  -30.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -38.0000   60.0000 55

  6 omega   -7.00   29.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -99.0000  -90.0000 36

  7 omega  -18.00   14.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -38.0000   60.0000 32
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0109140000
_diffrn_orient_matrix_UB_12      0.0624051000
_diffrn_orient_matrix_UB_13      -0.0095801000
_diffrn_orient_matrix_UB_21      0.0380671000
_diffrn_orient_matrix_UB_22      0.0242892000
_diffrn_orient_matrix_UB_23      0.0161123000
_diffrn_orient_matrix_UB_31      0.0234310000
_diffrn_orient_matrix_UB_32      -0.0105723000
_diffrn_orient_matrix_UB_33      -0.0194750000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1180
_diffrn_reflns_av_unetI/netI     0.1269
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            27606
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.91
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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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            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0042(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         8461
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.1495
_refine_ls_R_factor_gt           0.0834
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0970P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1967
_refine_ls_wR_factor_ref         0.2336
_reflns_number_gt                4360
_reflns_number_total             8461
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03431_si_002.cif
_cod_data_source_block           exp_3g
_cod_depositor_comments          'Adding full bibliography for 1544948.cif.'
_cod_database_code               1544948
_chemical_oxdiff_formula         'C1 H1 n1'
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C39(H39A,
 H39B), C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C16(H16), C17(H17), C19(H19), C20(H20), C23(H23), C24(H24), C26(H26),
 C27(H27), C32(H32), C44(H44), C45(H45), C47(H47), C48(H48), C51(H51), C52(H52),
  C54(H54), C55(H55)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C),
 C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C49(H49A,H49B,H49C), C56(H56A,H56B,
 H56C)
;
_olex2_date_sample_data_collection 2016-10-20
_olex2_submission_special_instructions 'No special instructions were received'