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_1570013
_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         'C14 H8 Cl I N4 O'
_chemical_formula_sum            'C14 H8 Cl I N4 O'
_chemical_formula_weight         410.59
_chemical_name_systematic
;
6-chloro-8-iodo-2-(4-methoxyphenyl)imidazo[1,2-a]pyrazine-3-carbonitrile
;
_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   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                75.6990(10)
_cell_angle_beta                 74.5870(10)
_cell_angle_gamma                80.1380(10)
_cell_formula_units_Z            2
_cell_length_a                   8.9084(3)
_cell_length_b                   8.9556(3)
_cell_length_c                   9.5787(3)
_cell_measurement_reflns_used    8936
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      35.8900
_cell_measurement_theta_min      2.8760
_cell_volume                     709.30(4)
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v3.0.21'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_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      173(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'mix of omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10790
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         3.163
_diffrn_source                   'rotating anode generator'
_exptl_absorpt_coefficient_mu    2.449
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_correction_T_min  0.6067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.922
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         1.195
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0246
_refine_ls_R_factor_gt           0.0220
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0253P)^2^+0.5053P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0551
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2610
_reflns_number_total             2820
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02893c2.cif
_cod_data_source_block           test2
_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 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1570012--1570015.cif.
;
_cod_database_code               1570013
_shelx_estimated_absorpt_t_min   0.441
_shelx_estimated_absorpt_t_max   0.710
_shelxl_version_number           2014-3
_shelx_res_checksum              676