Calculation-assisted regioselective functionalization of the imidazo[1,2-<i>a</i>]pyrazine scaffold <i>via</i> zinc and magnesium organometallic intermediates.
Kastrati, Agonist; Kremsmair, Alexander; Sunagatullina, Alisa S.; Korotenko, Vasilii; Guersoy, Yusuf C.; Rout, Saroj K.; Lima, Fabio; Brocklehurst, Cara E.; Karaghiosoff, Konstantin; Zipse, Hendrik; Knochel, Paul; Chemical science 14 (2023) 11261–11266; doi:10.1039/d3sc02893c

data_1570014
_publ_section_title
;
 Calculation-assisted regioselective functionalization of the
 imidazo[1,2-<i>a</i>]pyrazine scaffold <i>via</i> zinc and magnesium
 organometallic intermediates.
;
_journal_issue                   40
_journal_name_full               'Chemical science'
_journal_page_first              11261
_journal_page_last               11266
_journal_paper_doi               10.1039/d3sc02893c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C9 H8 Cl N3'
_chemical_formula_sum            'C9 H8 Cl N3'
_chemical_formula_weight         193.63
_chemical_name_systematic
;
5-allyl-6-chloroimidazo[1,2-a]pyrazine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2023-04-25 deposited with the CCDC.	2023-09-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.538(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2253(10)
_cell_length_b                   7.3421(4)
_cell_length_c                   9.4392(6)
_cell_measurement_reflns_used    3079
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.5660
_cell_measurement_theta_min      2.2090
_cell_volume                     878.64(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
;
_computing_publication_material
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
;
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14527
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.278
_diffrn_reflns_theta_min         3.206
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86303
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2173
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0520P)^2^+0.3383P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1163
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1735
_reflns_number_total             2173
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02893c2.cif
_cod_data_source_block           test1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 1570012--1570015.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1570014
_shelx_estimated_absorpt_t_min   0.861
_shelx_estimated_absorpt_t_max   0.981
_shelxl_version_number           2014-3
_shelx_res_checksum              12555