Stereoselective construction of functionalized tetracyclic and pentacyclic coumarinopyranpyrazole/pyrimidinedione/coumarin scaffolds using a solid-state melt reaction.
Bakthadoss, Manickam; Kannan, Damodharan; Sivakumar, Nagappan; Malathi, Palani; Manikandan, Vasudevan; Organic & biomolecular chemistry 13 (2015) 5597–5601; doi:10.1039/c5ob00442j

data_7154429
_publ_section_title
;
 Stereoselective construction of functionalized tetracyclic and
 pentacyclic coumarinopyranpyrazole/pyrimidinedione/coumarin scaffolds
 using a solid-state melt reaction.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5597
_journal_page_last               5601
_journal_paper_doi               10.1039/c5ob00442j
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         C22H18N2O5
_chemical_formula_sum            'C22 H18 N2 O5'
_chemical_formula_weight         390.38
_chemical_melting_point          512.1(10)
_chemical_name_common            'coumarinopyran pyrimidinedione'
_chemical_name_systematic
'4,6-dimethyl-9-phenyl-8,12-dioxa-4,6-diazatetracyclo[8.8.0.02,7.013,18]octadeca-2(7),13,15, 17-tetraene-3,5,11-trione'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-03-03 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.113(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.2039(8)
_cell_length_b                   12.3888(6)
_cell_length_c                   9.8162(5)
_cell_measurement_reflns_used    4875
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.51
_cell_measurement_theta_min      2.65
_cell_volume                     1830.46(16)
_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 (Macrae et al., 2008)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14679
_diffrn_reflns_theta_full        24.19
_diffrn_reflns_theta_max         24.19
_diffrn_reflns_theta_min         1.35
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_correction_T_min  0.9001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane, Ethyl acetate'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         2932
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0878P)^2^+0.8077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1598
_reflns_number_gt                2173
_reflns_number_total             2932
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob00442j2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '238-240 C' was changed to
'512.1(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 7154429.cif.
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7154429