One-Pot Five-Component Synthesis of Spirocyclopenta[b]chromene Derivatives and Their Acid-Catalyzed Rearrangement
Michael A. Terzidis; Tryfon Zarganes-Tzitzikas; Constantinos Tsimenidis; Julia Stephanidou-Stephanatou; Constantinos A. Tsoleridis; George E. Kostakis; Journal of Organic Chemistry 77 (2012) 9018–9028; doi:10.1021/jo3014947

data_4027590
_publ_section_title
;
 One-Pot Five-Component Synthesis of Spirocyclopenta[b]chromene
 Derivatives and Their Acid-Catalyzed Rearrangement
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9018
_journal_page_last               9028
_journal_paper_doi               10.1021/jo3014947
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C32 H35 N3 O10'
_chemical_formula_weight         621.63
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 104.630(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4645(13)
_cell_length_b                   14.0496(10)
_cell_length_c                   18.536(2)
_cell_measurement_reflns_used    7896
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.60
_cell_measurement_theta_min      1.69
_cell_volume                     3140.8(5)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_detector                 'image plate ( 34 cm diameter )'
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_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  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0906
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16575
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.65
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9729
_exptl_absorpt_correction_T_min  0.9617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         5891
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0305P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                2918
_reflns_number_total             5891
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3014947_si_005.cif
_cod_data_source_block           t572
_cod_original_cell_volume        3140.7(5)
_cod_database_code               4027590