Electrophilic alkylation of arenes with 5-bromopyrimidine en route to 4-aryl-5-alkynylpyrimidines
Shcherbakov, Stanislav S.; Magometov, Artyom Yu.; Shcherbakova, Viktoriia Yu.; Aksenov, Alexander V.; Domenyuk, Dmitriy A.; Zelensky, Vladimir A.; Rubin, Michael; RSC Advances 10 (2020) 10315–10321; doi:10.1039/D0RA01335H

data_7240105
_publ_section_title
;
 Electrophilic alkylation of arenes with 5-bromopyrimidine en route to
 4-aryl-5-alkynylpyrimidines
;
_journal_issue                   17
_journal_name_full               'RSC Advances'
_journal_page_first              10315
_journal_page_last               10321
_journal_paper_doi               10.1039/D0RA01335H
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C10 H7 Br N2 O'
_chemical_formula_sum            'C10 H7 Br N2 O'
_chemical_formula_weight         251.09
_chemical_name_systematic        4-(5-bromopyrimidin-4-yl)phenol
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-02-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-10 deposited with the CCDC.	2020-03-05 downloaded from the CCDC.
;
_cell_angle_alpha                77.439(2)
_cell_angle_beta                 76.725(2)
_cell_angle_gamma                87.542(2)
_cell_formula_units_Z            4
_cell_length_a                   9.0376(2)
_cell_length_b                   9.5049(2)
_cell_length_c                   11.5608(2)
_cell_measurement_reflns_used    15528
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      75.9270
_cell_measurement_theta_min      3.9860
_cell_volume                     943.39(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -116.00 -17.00   1.00    1.00    --  -41.35 -38.00  60.00   99
  2  \w   -116.00 -17.00   1.00    1.00    --  -41.35 -38.00 -60.00   99
  3  \w    -66.00  33.00   1.00    1.00    --  -41.35  38.00-120.00   99
  4  \w     23.00  97.00   1.00    1.00    --   41.35-125.00-120.00   74
  5  \w      1.00  82.00   1.00    1.00    --   41.35 -99.00 -30.00   81
  6  \w     23.00  97.00   1.00    1.00    --   41.35-125.00 120.00   74
  7  \w     79.00 178.00   1.00    1.00    --  112.00  77.00-120.00   99
  8  \w     86.00 178.00   1.00    1.00    --  112.00  45.00 -30.00   92
  9  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00 150.00   99
 10  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00-180.00  109
 11  \w     30.00 165.00   1.00    1.00    --  112.00 -15.00 -30.00  135
 12  \w     79.00 178.00   1.00    1.00    --  112.00  77.00 -90.00   99
 13  \w     36.00 116.00   1.00    1.00    --  112.00-111.00 -90.00   80
 14  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00   0.00  101
 15  \w     84.00 178.00   1.00    1.00    --  112.00  30.00-120.00   94
 16  \w    100.00 178.00   1.00    1.00    --  112.00 111.00  90.00   78
 17  \w     86.00 178.00   1.00    1.00    --  112.00  45.00-180.00   92
 18  \w     36.00 116.00   1.00    1.00    --  112.00-111.00   0.00   80
 19  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00   0.00   80
 20  \w     36.00 116.00   1.00    1.00    --  112.00-111.00-150.00   80
 21  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00-180.00   80
 22  \w     84.00 178.00   1.00    1.00    --  112.00  30.00 -60.00   94
 23  \w     39.00 138.00   1.00    1.00    --  112.00 -45.00  90.00   99
 24  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00   0.00  109
 25  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00  90.00  109
 26  \w     36.00 116.00   1.00    1.00    --  112.00-111.00 120.00   80
 27  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00  60.00   80
 28  \w     83.00 178.00   1.00    1.00    --  112.00  61.00  90.00   95
 29  \w     40.00 141.00   1.00    1.00    --  112.00 -61.00-150.00  101
 30  \w     36.00 145.00   1.00    1.00    --  112.00 -77.00-120.00  109
 31  \w    100.00 178.00   1.00    1.00    --  112.00 111.00-150.00   78
 32  \w     29.00 109.00   1.00    1.00    --  112.00 -94.00 120.00   80
 33  \w     83.00 178.00   1.00    1.00    --  112.00  61.00 150.00   95
 34  \w   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00-150.00  108
 35  \w   -117.00  -9.00   1.00    1.00    --  -41.35 -77.00 -90.00  108
 36  \w      9.00  71.00   1.00    1.00    --   41.35  77.00  30.00   62
 37  \w      6.00  34.00   1.00    1.00    --   41.35  87.00 112.93   28
 38  \w     30.00  56.00   1.00    1.00    --  112.00 -94.00 -90.00   26
 39  \w     73.00  99.00   1.00    1.00    --  112.00 -94.00 -90.00   26
 40  \w     35.00  61.00   1.00    1.00    --  112.00 -94.00  30.00   26
 41  \w     79.00 105.00   1.00    1.00    --  112.00-111.00-120.00   26
 42  \w     80.00 106.00   1.00    1.00    --  112.00 178.00 -60.00   26
 43  \w    153.00 178.00   1.00    1.00    --  112.00   0.00 -30.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1048254000
_diffrn_orient_matrix_UB_12      -0.0147954000
_diffrn_orient_matrix_UB_13      -0.0846953000
_diffrn_orient_matrix_UB_21      0.0675192000
_diffrn_orient_matrix_UB_22      -0.1493290000
_diffrn_orient_matrix_UB_23      -0.0112391000
_diffrn_orient_matrix_UB_31      -0.1230006000
_diffrn_orient_matrix_UB_32      -0.0711181000
_diffrn_orient_matrix_UB_33      0.1110948000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19731
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.180
_diffrn_reflns_theta_min         4.022
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.662
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.214
_refine_diff_density_max         0.685
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       0.0035(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3943
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0295
_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^)+(0.0393P)^2^+1.3812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0780
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3850
_reflns_number_total             3943
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra01335h2.cif
_cod_data_source_block           anna_stas99604_5
_cod_depositor_comments          'Adding full bibliography for 7240105.cif.'
_cod_database_code               7240105
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 98.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     76.86
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C12(H12), C11(H11), C6(H6), C19(H19), C7(H7), C1(H1A),
 C10(H10), C20(H20), C2(H2A), C9(H9)
;
_shelx_res_checksum              20221
_olex2_date_sample_data_collection 2019-10-30
_olex2_exptl_crystal_mounting_method
'Mounted on the glass stick by acrylic glue'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.974
_oxdiff_exptl_absorpt_empirical_full_min 0.654