Preparation of pyridopyrazines through tandem Pd-catalyzed C-N/C-C coupling reactions of Ugi adducts.
Takallou, Ahmad; Al-Siyabi, Munir; Al-Shidhani, Sulaiman; Lotfi Nosood, Yazdanbakhsh; Habibi, Azizollah; Almaani, Alhajaj; Anwar, Muhammad U.; Al-Harrasi, Ahmed; Organic & biomolecular chemistry 21 (2023) 9530–9533; doi:10.1039/d3ob01768k

data_7159692
_publ_section_title
;
 Preparation of pyridopyrazines through tandem Pd-catalyzed C-N/C-C
 coupling reactions of Ugi adducts.
;
_journal_issue                   48
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              9530
_journal_page_last               9533
_journal_paper_doi               10.1039/d3ob01768k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C25 H21 F N2 O2'
_chemical_formula_weight         400.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method
;FinalCif V121 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-05-28 deposited with the CCDC.	2023-11-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.6450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.9745(6)
_cell_length_b                   20.9846(8)
_cell_length_c                   7.8209(4)
_cell_measurement_reflns_used    6167
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.344
_cell_measurement_theta_min      2.7865
_cell_volume                     1993.27(15)
_computing_cell_refinement       'SAINT V8.40B'
_computing_data_collection
'Bruker BIS V6.2.16/2021-10-23 && APEX4 2022.10-0'
_computing_data_reduction        'SAINT V8.40B'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEXII'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 QUAZAR'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11556
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.392
_diffrn_reflns_theta_min         2.786
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction: 
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 
(2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.483
_exptl_crystal_size_mid          0.123
_exptl_crystal_size_min          0.045
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
;
 Flack x determined using 1538 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(4)
_refine_ls_extinction_coef       0.0093(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         4066
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0350
_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^)+(0.0357P)^2^+0.5586P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0877
_reflns_Friedel_coverage         0.986
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3500
_reflns_number_total             4066
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01768k2.cif
_cod_data_source_block           MU39_P_R1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7159692--7159693.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7159692
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.996
_diffrn_measurement_ambient_temperature_device_make '296 K'
_shelx_res_checksum              13299
_shelx_hkl_checksum              85924