Highly efficient regioselective synthesis of pyrroles via a tandem enamine formation‒Michael addition‒cyclization sequence under catalyst- and solvent-free conditions
Vivekanand, Thavaraj; Vinoth, Perumal; Agieshkumar, B.; Sampath, Natarajan; Sudalai, Arumugam; Menéndez, J. Carlos; Sridharan, Vellaisamy; Green Chem. 17 (2015) 3415–; doi:10.1039/C5GC00365B

data_7220409
_publ_section_title
;
 Highly efficient regioselective synthesis of pyrroles via a tandem
 enamine formation--Michael addition--cyclization sequence under catalyst-
 and solvent-free conditions
;
_journal_issue                   6
_journal_name_full               'Green Chem.'
_journal_page_first              3415
_journal_paper_doi               10.1039/C5GC00365B
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C29 H25 Cl N2 O3'
_chemical_formula_sum            'C29 H25 Cl N2 O3'
_chemical_formula_weight         484.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-02-09
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-02-09 deposited with the CCDC.
2015-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.880(7)
_cell_length_b                   16.051(8)
_cell_length_c                   26.140(13)
_cell_measurement_reflns_used    69152
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.591
_cell_measurement_theta_min      1.489
_cell_volume                     4985(5)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type
;
Goniometer Xcalibur, detector: Ruby
Oxford Diffraction (2007). Oxford Diffraction Ltd.,
Xcalibur CCD system
;
_diffrn_measurement_method       'w\ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1004
_diffrn_reflns_av_unetI/netI     0.1624
_diffrn_reflns_laue_measured_fraction_full 0.999
_diffrn_reflns_laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            69152
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.591
_diffrn_reflns_theta_min         1.489
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             2028
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_coef       0.0038(5)
_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   0.869
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     637
_refine_ls_number_reflns         12410
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.869
_refine_ls_R_factor_all          0.2031
_refine_ls_R_factor_gt           0.0466
_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^)+(0.0557P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1327
_reflns_Friedel_coverage         0.818
_reflns_friedel_fraction_full    1.000
_reflns_friedel_fraction_max     0.975
_reflns_number_gt                4635
_reflns_number_total             12410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5gc00365b2.cif
_cod_data_source_block           ms
_cod_depositor_comments          'Adding full bibliography for 7220409.cif.'
_cod_database_code               7220409
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.00(9) -0.00(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Riding coordinates:
 N2A(H2A), N2B(H2B)
3.b Ternary CH refined with riding coordinates:
 C18A(H18A), C18B(H18B)
3.c Secondary CH2 refined with riding coordinates:
 C11A(H11A,H11B), C28A(H28A,H28B), C11B(H11C,H11D)
3.d Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C7A(H7A), C9A(H9A), C10A(H10A), C13A(H13A), C14A(H14A), C15A(H15A),
 C16A(H16A), C17A(H17A), C22A(H22A), C23A(H23A), C24A(H24A), C25A(H25A),
 C6B(H6B), C7B(H7B), C9B(H9B), C10B(H10B), C13B(H13B), C14B(H14B), C15B(H15B),
 C16B(H16B), C17B(H17B), C22B(H22B), C23B(H23B), C24B(H24B), C25B(H25B),
 C28B(H28C)
3.e Idealised Me refined as rotating group:
 C26A(H26A,H26B,H26C), C29A(H29A,H29B,H29C), C26B(H26D,H26E,H26F), C29B(H29D,
 H29E,H29F)
;
_olex2_submission_special_instructions 'No special instructions were received'