A new route for the synthesis of highly substituted 4-aminoquinoline drug like molecules via aza hetero-Diels-Alder reaction.
Vidyacharan, Shinde; Sagar, A.; Sharada, Duddu S.; Organic & biomolecular chemistry 13 (2015) 7614–7618; doi:10.1039/c5ob01023c

data_7154547
_publ_section_title
;
 A new route for the synthesis of highly substituted 4-aminoquinoline drug
 like molecules via aza hetero-Diels-Alder reaction.
;
_journal_issue                   28
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7614
_journal_page_last               7618
_journal_paper_doi               10.1039/c5ob01023c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C20 H18 N2 O4'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36
_chemical_melting_point          354.1(10)
_chemical_name_common            4-aminoquinoline
_chemical_name_systematic
'dimethyl 4-(benzylamino)quinoline-2,3-dicarboxylate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-12-31
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_audit_update_record
;
2015-04-12 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.958(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.3579(11)
_cell_length_b                   10.6509(6)
_cell_length_c                   16.8297(14)
_cell_measurement_reflns_used    1936
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      70.5803
_cell_measurement_theta_min      4.5815
_cell_volume                     3456.9(4)
_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
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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
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega   -5.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   12.0000   90.0000 34

  2 omega  -77.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  111.0000   90.0000 52

  3 omega  -63.00  -10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   12.0000   90.0000 53

  4 omega  -10.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -120.0000 82

  5 omega  -16.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000   30.0000 98

  6 omega   67.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   30.0000 25

  7 omega   86.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  160.0000  -41.0000 26

  8 omega   46.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -30.0000 33

  9 omega  100.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 78

 10 omega   88.00  132.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -120.0000 44

 11 omega   39.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 58

 12 omega   89.00  167.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -60.0000 78

 13 omega   80.00  158.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 78

 14 omega   60.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 25

 15 omega   44.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 70

 16 omega   79.00  134.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 55
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0098092000
_diffrn_orient_matrix_UB_12      0.0777992000
_diffrn_orient_matrix_UB_13      0.0754225000
_diffrn_orient_matrix_UB_21      0.0191828000
_diffrn_orient_matrix_UB_22      0.1201429000
_diffrn_orient_matrix_UB_23      -0.0440123000
_diffrn_orient_matrix_UB_31      -0.0769290000
_diffrn_orient_matrix_UB_32      0.0201805000
_diffrn_orient_matrix_UB_33      -0.0287784000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6934
_diffrn_reflns_theta_full        70.67
_diffrn_reflns_theta_max         70.67
_diffrn_reflns_theta_min         4.59
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.780
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74363
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1472
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0564
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1702
_reflns_number_gt                2067
_reflns_number_total             3258
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01023c2.cif
_cod_data_source_block           exp_2959_216
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '80-82 degree celcius' was changed to
'354.1(10)' - it was converted from degrees Celsius(C) to Kelvins(K),
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 7154546--7154547.cif.
;
_cod_database_code               7154547
_chemical_oxdiff_formula         'C20 H18 N2 O4'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97