Expansion of Azulenes as Nonbenzenoid Aromatic Compounds for C–H Activation: Rhodium- and Iridium-Catalyzed Oxidative Cyclization of Azulene Carboxylic Acids with Alkynes for the Synthesis of Azulenolactones and Benzoazulenes
Maeng, Chanyoung; Son, Jeong-Yu; Lee, Seung Cheol; Baek, Yonghyeon; Um, Kyusik; Han, Sang Hoon; Ko, Gi Hoon; Han, Gi Uk; Lee, Kyungsup; Lee, Kooyeon; Lee, Phil Ho; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.9b03448

data_4037909
_publ_section_title
;
 Expansion of Azulenes as Nonbenzenoid Aromatic Compounds for C--H
 Activation: Rhodium- and Iridium-Catalyzed Oxidative Cyclization of
 Azulene Carboxylic Acids with Alkynes for the Synthesis of
 Azulenolactones and Benzoazulenes
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03448
_journal_year                    2020
_chemical_formula_sum            'C38 H26'
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_atom_sites_solution_hydrogens   geom
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_cell_length_b                   14.175(4)
_cell_length_c                   16.004(5)
_cell_measurement_reflns_used    5853
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      22.03
_cell_measurement_theta_min      2.44
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_computing_cell_refinement       'Bruker APEXIII'
_computing_data_collection       'Bruker APEXIII'
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_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Photon 100 CMOS detector'
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_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_point_group_measured_fraction_max 0.998
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_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.437
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       rod
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.343
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.098
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.237
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_refine_ls_extinction_method     none
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_refine_ls_number_reflns         10261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.1422
_refine_ls_R_factor_gt           0.0678
_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^)+(0.0622P)^2^+2.3662P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5622
_reflns_number_total             10261
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03448_si_003.cif
_cod_data_source_block           A19042O_002_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        2614.8(14)
_cod_database_code               4037909
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              85306
_shelx_hkl_checksum              87361
_shelx_fab_checksum              64469