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_1570015
_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         'C7 H2 Cl I N4'
_chemical_formula_sum            'C7 H2 Cl I N4'
_chemical_formula_weight         304.48
_chemical_name_systematic
;
6-chloro-2-iodoimidazo[1,2-a]pyrazine-3-carbonitrile
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 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                 99.8020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2171(2)
_cell_length_b                   5.69960(10)
_cell_length_c                   18.6448(5)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      36.3227
_cell_measurement_theta_min      2.5704
_cell_volume                     860.47(3)
_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 0.992
_diffrn_measured_fraction_theta_max 0.995
_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  0.0344
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18326
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.506
_diffrn_reflns_theta_min         3.743
_diffrn_source                   'rotating anode generator'
_exptl_absorpt_coefficient_mu    3.983
_exptl_absorpt_correction_T_max  0.7410
_exptl_absorpt_correction_T_min  0.6679
_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    2.350
_exptl_crystal_description       platelet
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2609
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0184
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0022P)^2^+0.9066P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0369
_refine_ls_wR_factor_ref         0.0386
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2296
_reflns_number_total             2609
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc02893c2.cif
_cod_data_source_block           test1_CCDC2
_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_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1570015
_shelx_estimated_absorpt_t_min   0.691
_shelx_estimated_absorpt_t_max   0.925
_shelxl_version_number           2014-3
_shelx_res_checksum              84725