Solid-state melt reaction for the domino process: highly efficient synthesis of fused tetracyclic chromenopyran pyrimidinediones using Baylis-Hillman derivatives.
Bakthadoss, Manickam; Sivakumar, Govindan; Kannan, Damodharan; Organic letters 11 (2009) 4466–4469; doi:10.1021/ol901228j

data_1504036
_publ_section_title
;
 Solid-state melt reaction for the domino process: highly efficient
 synthesis of fused tetracyclic chromenopyran pyrimidinediones using
 Baylis-Hillman derivatives.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4466
_journal_page_last               4469
_journal_paper_doi               10.1021/ol901228j
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C24 H22 N2 O6'
_chemical_formula_sum            'C24 H22 N2 O6'
_chemical_formula_weight         434.44
_chemical_melting_point          211(1)
_chemical_name_common            'Compound 4a'
_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                102.951(2)
_cell_angle_beta                 104.668(2)
_cell_angle_gamma                104.178(2)
_cell_formula_units_Z            2
_cell_length_a                   9.9987(5)
_cell_length_b                   10.4124(4)
_cell_length_c                   11.1163(5)
_cell_measurement_reflns_used    6739
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.64
_cell_measurement_theta_min      1.99
_cell_volume                     1033.75(8)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD diffractometer'
_diffrn_measurement_method       '\w and \f scan'
_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  0.0221
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27288
_diffrn_reflns_theta_full        31.64
_diffrn_reflns_theta_max         31.64
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9741
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.015(3)
_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   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         6923
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0821P)^2^+0.1661P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1366
_refine_ls_wR_factor_ref         0.1539
_reflns_number_gt                5109
_reflns_number_total             6923
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol901228j_si_002.cif
_cod_data_source_block           mg41
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1504036