Selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles via tandem reactions of alkynones with pyrrole derivatives
Zhao, Yu-Lei; Yuan, Yang; Xu, Murong; Zheng, Zhong; Zhang, Runhua; LI, Yanzhong; Org. Biomol. Chem.  (2017) –; doi:10.1039/C7OB01516J

data_7155763
_publ_section_title
;
 Selective synthesis of pyrrolo[1,2-a]azepines or 4,6-dicarbonyl indoles
 via tandem reactions of alkynones with pyrrole derivatives
;
_journal_name_full               'Org. Biomol. Chem.'
_journal_paper_doi               10.1039/C7OB01516J
_journal_year                    2017
_chemical_formula_moiety         'C29 H22 N2 O3'
_chemical_formula_sum            'C29 H22 N2 O3'
_chemical_formula_weight         446.49
_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             2016-08-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-01-17 deposited with the CCDC.
2017-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                81.864(6)
_cell_angle_beta                 89.495(5)
_cell_angle_gamma                89.905(5)
_cell_formula_units_Z            4
_cell_length_a                   10.396(3)
_cell_length_b                   12.966(4)
_cell_length_c                   16.944(5)
_cell_measurement_reflns_used    1651
_cell_measurement_temperature    296
_cell_measurement_theta_max      20.908
_cell_measurement_theta_min      2.314
_cell_volume                     2260.9(12)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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      296
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.1016
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            15906
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.587
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0703 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.8213.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0118(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     616
_refine_ls_number_reflns         8408
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.1584
_refine_ls_R_factor_gt           0.0724
_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^)+(0.1030P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1784
_refine_ls_wR_factor_ref         0.2253
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3880
_reflns_number_total             8408
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob01516j2.cif
_cod_data_source_block           mo_dm16500_0m
_cod_database_code               7155763
_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:
 C1(H1A,H1B), C30(H30A,H30B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26), C27(H27), C28(H28),
  C29(H29), C31(H31), C34(H34), C37(H37), C40(H40), C41(H41), C42(H42),
 C43(H43), C44(H44), C48(H48), C49(H49), C51(H51), C52(H52), C54(H54), C55(H55),
  C56(H56), C57(H57), C58(H58)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C45(H45A,H45B,H45C)
;
_shelx_res_checksum              3210
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'