Efficient synthesis of functionalized dihydroquinolines, quinolines and dihydrobenzo[b]azepine via an iron(iii) chloride-catalyzed intramolecular alkyne-carbonyl metathesis of alkyne tethered 2-amino benzaldehyde/acetophenone derivatives.
Jalal, Swapnadeep; Bera, Krishnendu; Sarkar, Soumen; Paul, Kartick; Jana, Umasish; Organic & biomolecular chemistry 12 (2014) 1759–1770; doi:10.1039/c3ob42292e

data_7153607
_publ_section_title
;
 Efficient synthesis of functionalized dihydroquinolines, quinolines and
 dihydrobenzo[b]azepine via an iron(iii) chloride-catalyzed intramolecular
 alkyne-carbonyl metathesis of alkyne tethered 2-amino
 benzaldehyde/acetophenone derivatives.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1759
_journal_page_last               1770
_journal_paper_doi               10.1039/c3ob42292e
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C24 H21 N O3 S'
_chemical_formula_weight         403.48
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.100(3)
_cell_angle_beta                 90.343(3)
_cell_angle_gamma                93.898(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3806(3)
_cell_length_b                   11.1445(4)
_cell_length_c                   13.0469(5)
_cell_measurement_reflns_used    250
_cell_measurement_temperature    278(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      1.6
_cell_volume                     1161.56(8)
_computing_cell_refinement       'SMART APEX II'
_computing_data_collection       'SMART APEX II (Bruker,2010)'
_computing_data_reduction        'SAINT (Bruker,2000)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      278(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19204
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_diffrn_reflns_theta_max         27.17
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.9482
_exptl_absorpt_correction_T_min  0.8573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
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_exptl_crystal_size_max          0.08
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_platon_squeeze_details
;
;
_refine_diff_density_max         0.191
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_refine_ls_matrix_type           full
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_refine_ls_number_reflns         5125
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0922
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_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1290
_reflns_number_gt                2939
_reflns_number_total             5125
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            c3ob42292e.txt
_cod_data_source_block           UJ1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1161.55(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7153607