Copper(I)-Y zeolite catalyzed N-sulfonylketenimine mediated annulation of hydroxynaphthoquinones: syntheses of naphtho[2,1-b]furan-2,5-diones and benzo[de]chromene-2,6-diones
Devenderan Ramanathan; Kayambu Namitharan; Kasi Pitchumani; Chem.Commun. 52 (2016) 8436–; doi:

data_7119677
_publ_section_title
;
 Copper(I)-Y zeolite catalyzed N-sulfonylketenimine mediated annulation of
 hydroxynaphthoquinones: syntheses of naphtho[2,1-b]furan-2,5-diones and
 benzo[de]chromene-2,6-diones
;
_journal_name_full               Chem.Commun.
_journal_page_first              8436
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C19 H12 O4'
_chemical_formula_weight         304.29
_chemical_name_common            3-(2-methoxyphenyl)benzo[de]chromene-2,6-dione
_chemical_name_systematic        3-(2-methoxyphenyl)benzo[de]chromene-2,6-dione
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-02-27 deposited with the CCDC.
2016-06-06 downloaded from the CCDC.
;
_cell_angle_alpha                100.217(2)
_cell_angle_beta                 105.699(2)
_cell_angle_gamma                108.9389(19)
_cell_formula_units_Z            4
_cell_length_a                   8.4472(4)
_cell_length_b                   12.7834(5)
_cell_length_c                   15.0002(6)
_cell_measurement_reflns_used    4755
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.60
_cell_volume                     1411.00(11)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20230
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.474
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       Square
_exptl_crystal_F_000             632
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0039(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         4954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0367P)^2^+1.4698P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3545
_reflns_number_total             4954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc03571j2.cif
_cod_data_source_block           5hc7
_cod_database_code               7119677
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.975
_shelx_estimated_absorpt_t_max   0.984
_shelx_res_checksum              50558
_solvent_exptl_crystal_recrystallization_method Acetonitrile