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_4027589
_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 H34 Cl N3 O10'
_chemical_formula_weight         656.07
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.019(4)
_cell_length_b                   15.495(3)
_cell_length_c                   23.592(5)
_cell_measurement_reflns_used    20494
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      24.61
_cell_measurement_theta_min      1.31
_cell_volume                     6587(2)
_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 0.998
_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  0.0734
_diffrn_reflns_av_sigmaI/netI    0.0523
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            34767
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.127
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.107
_refine_ls_extinction_coef       0.0020(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   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5792
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.1753
_refine_ls_R_factor_gt           0.1529
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0261P)^2^+90.1831P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3297
_refine_ls_wR_factor_ref         0.3380
_reflns_number_gt                4243
_reflns_number_total             5792
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3014947_si_004.cif
_cod_data_source_block           pbca
_cod_database_code               4027589