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_4037908
_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            'C25 H16 O2'
_chemical_formula_weight         348.38
_space_group_crystal_system      triclinic
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_atom_sites_solution_hydrogens   geom
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_cell_length_b                   13.2340(6)
_cell_length_c                   14.8269(7)
_cell_measurement_reflns_used    9892
_cell_measurement_temperature    120(2)
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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
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_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Photon 100 CMOS detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_limit_l_min       -18
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_diffrn_reflns_theta_max         27.081
_diffrn_reflns_theta_min         1.429
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       plate
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_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.214
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_refine_ls_extinction_method     none
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_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0398P)^2^+0.4098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0963
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5669
_reflns_number_total             7738
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03448_si_001.cif
_cod_data_source_block           A149O_002
_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_database_code               4037908
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              61128
_shelx_hkl_checksum              1872