Condensation of malononitrile with salicylaldehydes and o-aminobenzaldehydes revisited: solvent and catalyst free synthesis of 4H-chromenes and quinolines
Bhat, Subrahmanya Ishwar; Choudhury, Angshuman Roy; Trivedi, Darshak R.; RSC Advances 2 (2012) 10556–; doi:10.1039/c2ra21849f

data_7238747
_publ_section_title
;
 Condensation of malononitrile with salicylaldehydes and
 o-aminobenzaldehydes revisited: solvent and catalyst free synthesis of
 4H-chromenes and quinolines
;
_journal_issue                   28
_journal_name_full               'RSC Advances'
_journal_page_first              10556
_journal_paper_doi               10.1039/c2ra21849f
_journal_volume                  2
_journal_year                    2012
_chemical_formula_moiety         'C13 H8 N4 O'
_chemical_formula_sum            'C13 H8 N4 O'
_chemical_formula_weight         236.23
_chemical_melting_point          152
_chemical_name_systematic        (2-Amino-3-cyano-4H-chromene-4-yl)malononitrile
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                103.057(7)
_cell_angle_beta                 90.883(8)
_cell_angle_gamma                96.555(8)
_cell_formula_units_Z            2
_cell_length_a                   5.6073(8)
_cell_length_b                   8.1748(11)
_cell_length_c                   12.5000(17)
_cell_measurement_temperature    296(2)
_cell_volume                     554.02(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.938
_diffrn_measured_fraction_theta_max 0.938
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1222
_diffrn_reflns_av_sigmaI/netI    0.0804
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3766
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.67
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.11(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         1846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0540
_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^)+(0.1063P)^2^+0.0153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1526
_reflns_number_gt                1594
_reflns_number_total             1846
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ra21849f.txt
_cod_data_source_block           e113_0m
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7238747