Sequential σ-Bond Insertion/Benzannulation Involving Arynes: Selective Synthesis of Polysubstituted Naphthalenes.
Shu, Wen-Ming; Liu, Shan; He, Jian-Xin; Wang, Shuai; Wu, An-Xin; The Journal of organic chemistry 83 (2018) 9156–9165; doi:10.1021/acs.joc.8b01207

data_4035360
_publ_section_title
;
 Sequential \s-Bond Insertion/Benzannulation Involving Arynes: Selective
 Synthesis of Polysubstituted Naphthalenes.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9156
_journal_page_last               9165
_journal_paper_doi               10.1021/acs.joc.8b01207
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C21 H15 N O4'
_chemical_formula_weight         345.34
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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                 97.342(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.228(2)
_cell_length_b                   8.9299(14)
_cell_length_c                   14.873(2)
_cell_measurement_reflns_used    3244
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      29.18
_cell_measurement_theta_min      2.21
_cell_volume                     1742.5(4)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
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_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15568
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9891
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.212
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_refine_ls_extinction_method     none
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_refine_ls_number_parameters     237
_refine_ls_number_reflns         5058
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0517
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0848P)^2^+0.1524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1720
_reflns_number_gt                3049
_reflns_number_total             5058
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01207_si_003.cif
_cod_data_source_block           mo_150529f_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1742.5(5)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4035360