A competitive and highly selective 7-, 6- and 5-annulation with 1,3-migration through C-H and N-H - alkyne coupling.
Ajarul, Sk; Kayet, Anirban; Pati, Tanmay K.; Maiti, Dilip K.; Chemical communications (Cambridge, England) 56 (2020) 474–477; doi:10.1039/c9cc07360d

data_7125638
_publ_section_title
;
 A competitive and highly selective 7-, 6- and 5-annulation with
 1,3-migration through C-H and N-H - alkyne coupling.
;
_journal_issue                   3
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              474
_journal_page_last               477
_journal_paper_doi               10.1039/c9cc07360d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C23 H17 N O2'
_chemical_formula_weight         339.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2019-04-19 deposited with the CCDC.	2019-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                73.867(4)
_cell_angle_beta                 70.650(4)
_cell_angle_gamma                78.883(4)
_cell_formula_units_Z            2
_cell_length_a                   9.2441(16)
_cell_length_b                   9.5954(16)
_cell_length_c                   10.6672(18)
_cell_measurement_reflns_used    890
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.176
_cell_measurement_theta_min      2.223
_cell_volume                     852.3(3)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21150
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.176
_diffrn_reflns_theta_min         2.223
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABAS
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             356
_exptl_transmission_factor_max   0.755
_exptl_transmission_factor_min   0.639
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0632P)^2^+0.3097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1445
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3048
_reflns_number_total             3744
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07360d2.cif
_cod_data_source_block           shelx
_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/RSC/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 

 Adding full bibliography for 7125638--7125639.cif.
;
_cod_database_code               7125638
_shelx_shelxl_version_number     2017/1
_shelx_res_checksum              88873