Synthesis of new chromeno-annulated cis-fused pyrano[3,4-c]pyran derivatives via domino Knoevenagel–hetero-Diels–Alder reactions and their biological evaluation towards antiproliferative activity
Venkatesham, A.; Rao, R. Srinivasa; Nagaiah, K.; Yadav, J. S.; RoopaJones, G.; Basha, S. J.; Sridhar, B.; Addlagatta, A.; MedChemComm 3 (2012) 652–; doi:10.1039/c2md20023f

data_7112571
_publ_section_title
;
 Synthesis of new chromeno-annulated cis-fused pyrano[3,4-c]pyran
 derivatives via domino Knoevenagel--hetero-Diels--Alder reactions and
 their biological evaluation towards antiproliferative activity
;
_journal_issue                   6
_journal_name_full               MedChemComm
_journal_page_first              652
_journal_paper_doi               10.1039/c2md20023f
_journal_volume                  3
_journal_year                    2012
_chemical_formula_moiety         'C22 H22 O5'
_chemical_formula_sum            'C22 H22 O5'
_chemical_formula_weight         366.40
_chemical_name_systematic
;
2,2,8,-Trimethyl-2a,3,10c,12,13,14-hexahydro-2H-1,4,10-trioxa-dibenzo[c.g]
phenanthrene-7,11-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.214(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.4539(11)
_cell_length_b                   7.4613(5)
_cell_length_c                   16.2148(11)
_cell_measurement_reflns_used    9849
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      2.59
_cell_volume                     1795.3(2)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w 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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16576
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.14
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0732P)^2^+0.7442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                2889
_reflns_number_total             3161
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            c2md20023f.txt
_cod_data_source_block           af24m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7112571