Naphthoquinone-directed C-h annulation and csp(3)-h bond cleavage: one-pot synthesis of tetracyclic naphthoxazoles.
Wang, Meining; Zhang, Chi; Sun, Li-Ping; Ding, Chunyong; Zhang, Ao; The Journal of organic chemistry 79 (2014) 4553–4560; doi:10.1021/jo500572u

data_4029378
_publ_section_title
;
 Naphthoquinone-directed C-h annulation and csp(3)-h bond cleavage:
 one-pot synthesis of tetracyclic naphthoxazoles.
;
_journal_issue                   10
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4553
_journal_page_last               4560
_journal_paper_doi               10.1021/jo500572u
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C27 H19 N O2'
_chemical_formula_weight         389.43
_space_group_IT_number           2
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_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                77.753(4)
_cell_angle_beta                 86.780(4)
_cell_angle_gamma                80.766(4)
_cell_formula_units_Z            2
_cell_length_a                   5.7246(10)
_cell_length_b                   10.9332(18)
_cell_length_c                   16.289(3)
_cell_measurement_reflns_used    1209
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.030
_cell_measurement_theta_min      5.119
_cell_volume                     983.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5750
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.93
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10661
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.231
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.121
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0946P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1787
_reflns_number_gt                2263
_reflns_number_total             3631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo500572u_si_002.cif
_cod_data_source_block           cd213380
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029378.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4029378