Synthesis of Acridines and Persubstituted Phenols from Cyclobutenones and Active Methylene Ketones
Xiao-Dan Han; Yu-Long Zhao; Jia Meng; Chuan-Qing Ren; Qun Liu; Journal of Organic Chemistry 77 (2012) 5173–5178; doi:10.1021/jo300615t

data_4027234
_publ_section_title
;
 Synthesis of Acridines and Persubstituted Phenols from Cyclobutenones and
 Active Methylene Ketones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5173
_journal_page_last               5178
_journal_paper_doi               10.1021/jo300615t
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C20 H23 N O4'
_chemical_formula_weight         341.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.108(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5109(12)
_cell_length_b                   17.890(2)
_cell_length_c                   10.9068(13)
_cell_measurement_reflns_used    3250
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.21
_cell_volume                     1832.4(4)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_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  0.0506
_diffrn_reflns_av_sigmaI/netI    0.0537
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11004
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_description       blcok
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3205
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1289
_refine_ls_R_factor_gt           0.0720
_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^)+(0.0960P)^2^+0.7745P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1749
_refine_ls_wR_factor_ref         0.2117
_reflns_number_gt                1834
_reflns_number_total             3205
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300615t_si_002.cif
_cod_data_source_block           p21n
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               4027234