Nickel-Catalyzed Oxidative C-H/N-H Annulation of N-Heteroaromatic Compounds with Alkynes
Obata, Atsushi; Sasagawa, Akane; Yamazaki, Ken; Ano, Yusuke; Chatani, Naoto; Chemical Science  (2019) –; doi:10.1039/C8SC05063E

data_1550555
_publ_section_title
;
 Nickel-Catalyzed Oxidative C-H/N-H Annulation of N-Heteroaromatic
 Compounds with Alkynes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC05063E
_journal_year                    2019
_chemical_formula_moiety         'C22 H16 N2, 0.5(H2 O)'
_chemical_formula_sum            'C22 H17 N2 O0.5'
_chemical_formula_weight         317.39
_chemical_name_systematic        4j
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2018-09-18 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.390(4)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   19.1394(8)
_cell_length_b                   8.9002(3)
_cell_length_c                   19.2392(8)
_cell_measurement_reflns_used    8522
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.61
_cell_measurement_theta_min      2.24
_cell_volume                     3127.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      123
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.816
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15421
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        30.630
_diffrn_reflns_theta_max         30.630
_diffrn_reflns_theta_min         2.219
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            paleyellow
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1336.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.69
_refine_diff_density_min         -0.46
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0531
_refine_ls_shift/su_max          0.012
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0838P)^2^+3.7009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1453
_refine_ls_wR_factor_ref         0.1548
_reflns_number_gt                3530
_reflns_number_total             3947
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            c8sc05063e2.cif
_cod_data_source_block           xcalibur
_cod_depositor_comments
;

2019-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C44 H34 N4 O'
_cod_original_formula_weight         634.78
_cod_original_formula_moiety         'C44 H34 N4 O'
_cod_original_formula_units_Z            4
_cod_database_code               1550555