The Baylis–Hillman acetates in organic synthesis: Unprecedented sodium nitrite induced intramolecular Friedel–Crafts cyclization of secondary nitro compounds
Basavaiah, Deevi; Reddy, Daggula Mallikarjuna; RSC Adv. 4 (2014) 23966–; doi:10.1039/C4RA03573A

data_7235696
_publ_section_title
;
 The Baylis--Hillman acetates in organic synthesis: Unprecedented sodium
 nitrite induced intramolecular Friedel--Crafts cyclization of secondary
 nitro compounds
;
_journal_issue                   46
_journal_name_full               'RSC Adv.'
_journal_page_first              23966
_journal_paper_doi               10.1039/C4RA03573A
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C20 H18 O3'
_chemical_formula_sum            'C20 H18 O3'
_chemical_formula_weight         306.34
_chemical_melting_point          363(1)
_chemical_name_common            naphthalane
_chemical_name_systematic
; 
 methyl 4-benzyl-5-methoxynaphthalene-2-carboxylate 
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.098(15)
_cell_angle_beta                 80.854(12)
_cell_angle_gamma                89.732(16)
_cell_formula_units_Z            2
_cell_length_a                   8.1761(14)
_cell_length_b                   8.3698(19)
_cell_length_c                   12.1493(14)
_cell_measurement_reflns_used    1628
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.2760
_cell_measurement_theta_min      3.4980
_cell_volume                     796.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_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  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0410
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4790
_diffrn_reflns_theta_full        24.70
_diffrn_reflns_theta_max         24.70
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9749
_exptl_absorpt_correction_T_min  0.9668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       black
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2712
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.003
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0846P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1566
_reflns_number_gt                1812
_reflns_number_total             2712
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra03573a2.cif
_cod_data_source_block           4c-o
_cod_original_cell_volume        796.3(2)
_cod_database_code               7235696