An efficient microwave-assisted synthesis of cotinine and iso-cotinine analogs from an Ugi-4CR approach.
Polindara-García, Luis A; Montesinos-Miguel, Dario; Vazquez, Alfredo; Organic & biomolecular chemistry 13 (2015) 9065–9071; doi:10.1039/c5ob01170a

data_7154597
_publ_section_title
;
 An efficient microwave-assisted synthesis of cotinine and iso-cotinine
 analogs from an Ugi-4CR approach.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9065
_journal_page_last               9071
_journal_paper_doi               10.1039/c5ob01170a
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C22 H26 Cl N3 O2'
_chemical_formula_sum            'C22 H26 Cl N3 O2'
_chemical_formula_weight         399.913
_chemical_melting_point          433.0(10)
_chemical_name_systematic
'N-(tert-butyl)-1-(4-chlorophenethyl)-5-oxo-2-(pyridin-3-yl)pyrrolidine-2-carboxamide '
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-04-06T17:43:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-06-08 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.623(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6870(4)
_cell_length_b                   9.1043(3)
_cell_length_c                   21.0968(6)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     1.54184
_cell_volume                     2029.47(12)
_computing_cell_refinement
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
        (compiled Oct 27 2011,15:02:11) 
;
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.97
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            8247
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.97
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.417
_diffrn_reflns_theta_min         4.184
_exptl_absorpt_coefficient_mu    1.845
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method 'Slow evaporation of CDCl3 solution'
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     357
_refine_ls_number_reflns         3967
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0655P)^2^+0.7462P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1276
_reflns_number_gt                3277
_reflns_number_total             3967
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob01170a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '432-434' was changed to '433.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7154597.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7154597