Synthesis of medium-sized (6-7-6) ring compounds by iron-catalyzed C-H activation/annulation [corrected].
Panda, Niranjan; Mattan, Irshad; Ojha, Subhadra; Purohit, Chandra Shekhar; Organic & biomolecular chemistry 16 (2018) 7861–7870; doi:10.1039/c8ob01496e

data_7156466
_publ_section_title
;
 Synthesis of medium-sized (6-7-6) ring compounds by iron-catalyzed C-H
 activation/annulation [corrected].
;
_journal_issue                   42
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7861
_journal_page_last               7870
_journal_paper_doi               10.1039/c8ob01496e
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C20 H13 N O3'
_chemical_formula_sum            'C20 H13 N O3'
_chemical_formula_weight         315.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc204bs9
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_audit_update_record
;
2018-09-26 deposited with the CCDC.
2018-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.408(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2086(2)
_cell_length_b                   12.6711(4)
_cell_length_c                   8.3699(3)
_cell_measurement_reflns_used    5021
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      79.1610
_cell_measurement_theta_min      6.1990
_cell_volume                     756.30(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6678
_diffrn_reflns_point_group_measured_fraction_full 0.861
_diffrn_reflns_point_group_measured_fraction_max 0.814
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.882
_diffrn_reflns_theta_min         5.342
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.765
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_description       needle
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 875 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.33(19)
_refine_ls_extinction_coef       0.008(2)
_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   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0771P)^2^+0.0207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1204
_reflns_Friedel_coverage         0.593
_reflns_Friedel_fraction_full    0.708
_reflns_Friedel_fraction_max     0.635
_reflns_number_gt                2509
_reflns_number_total             2685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01496e2.cif
_cod_data_source_block           np_no2
_cod_depositor_comments          'Adding full bibliography for 7156466.cif.'
_cod_database_code               7156466
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              9883