Synthesis of Bi-, Ter-, and Quaterpyridinecarboxylates via Propargylisoxazole-Pyridine Rearrangement.
Galenko, Ekaterina E.; Kryukova, Mariya A.; Novikov, Mikhail S.; Khlebnikov, Alexander F.; The Journal of organic chemistry 85 (2020) 6109–6122; doi:10.1021/acs.joc.0c00611

data_4038260
_publ_section_title
;
 Synthesis of Bi-, Ter-, and Quaterpyridinecarboxylates via
 Propargylisoxazole-Pyridine Rearrangement.
;
_journal_issue                   9
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6109
_journal_page_last               6122
_journal_paper_doi               10.1021/acs.joc.0c00611
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C24 H18 N4 O4'
_chemical_formula_sum            'C24 H18 N4 O4'
_chemical_formula_weight         426.42
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.031(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.80570(10)
_cell_length_b                   9.6433(2)
_cell_length_c                   26.0047(5)
_cell_measurement_reflns_used    12398
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      77.3330
_cell_measurement_theta_min      3.3450
_cell_volume                     1957.13(6)
_computing_cell_refinement       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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    -43.00 -10.00   0.50    0.13    --  -47.20  42.00 -40.00   66
  2  \w    -68.00 -42.00   0.50    0.53    -- -106.00  61.00  90.00   52
  3  \w    -71.00 -41.00   0.50    0.53    -- -106.00  61.00 150.00   60
  4  \w    -70.00 -40.00   0.50    0.53    -- -106.00  61.00 120.00   60
  5  \w    -71.00 -33.00   0.50    0.53    -- -106.00  61.00  60.00   76
  6  \w    -71.00 -45.00   0.50    0.53    -- -106.00  61.00 -30.00   52
  7  \w    -70.00 -34.00   0.50    0.53    -- -106.00  61.00-120.00   72
  8  \w    -70.00 -44.00   0.50    0.53    -- -106.00  61.00-180.00   52
  9  \w   -127.00 -90.00   0.50    0.53    -- -106.00 -61.00 -90.00   74
 10  \w   -172.00 -95.00   0.50    0.53    -- -106.00 -45.00-120.00  154
 11  \w   -177.00-134.00   0.50    0.53    -- -106.00 -61.00 -90.00   86
 12  \w   -119.00 -41.00   0.50    0.13    --  -47.20 -42.00 167.00  156
 13  \w     45.00 110.00   0.50    0.13    --   47.20  42.00 -40.00  130
 14  \w     99.00 136.00   0.50    0.53    --  107.75  42.00 -40.00   74
 15  \w    106.00 175.00   0.50    0.53    --  107.75  30.00  90.00  138
 16  \w     74.00 103.00   0.50    0.53    --  107.75 -77.00 -30.00   58
 17  \w     62.00 102.00   0.50    0.53    --  107.75 -94.00  30.00   80
 18  \w     36.00  66.00   0.50    0.53    --  107.75 -77.00 -30.00   60
 19  \w     62.00  87.00   0.50    0.53    --  107.75 -77.00-120.00   50
 20  \w     47.00  72.00   0.50    0.53    --  107.75-125.00-150.00   50
 21  \w     78.00 112.00   0.50    0.53    --  107.75-125.00-150.00   68
 22  \w     35.00  60.00   0.50    0.53    --  107.75 -61.00-150.00   50
 23  \w    -26.00  26.00   0.50    0.13    --   47.20 -19.00   0.00  104
 24  \w    -10.00  23.00   0.50    0.13    --   47.20 -19.00  30.00   66
 25  \w    -16.00  31.00   0.50    0.13    --   47.20 -42.00 167.00   94
 26  \w     37.00  63.00   0.50    0.53    --  107.75 -61.00 120.00   52
 27  \w   -158.00 -93.00   0.50    0.53    -- -106.00 -42.00 167.00  130
 28  \w    138.00 164.00   0.50    0.53    --  107.75  42.00 -40.00   52
 29  \w     37.00  87.00   0.50    0.13    --   47.20  57.00 120.00  100
 30  \w     94.00 120.00   0.50    0.13    --   47.20 125.00-120.00   52
 31  \w     38.00  89.00   0.50    0.13    --   47.20  57.00  60.00  102
 32  \w    -14.00  11.00   0.50    0.13    --   47.20 -19.00-180.00   50
 33  \w   -153.00 -92.00   0.50    0.53    -- -106.00 -54.00  48.63  122
 34  \w   -119.00 -92.00   0.50    0.53    -- -106.00 -43.00  70.75   54
 35  \w    -61.00 -35.00   0.50    0.53    -- -106.00  61.00  90.00   52
 36  \w   -173.00-147.00   0.50    0.53    -- -106.00 -61.00 -60.00   52
 37  \w   -120.00 -87.00   0.50    0.53    -- -106.00 -68.00  27.38   66
 38  \w   -115.00 -83.00   0.50    0.53    -- -106.00 -77.00  60.00   64
 39  \w   -161.00-135.00   0.50    0.53    -- -106.00 -77.00 120.00   52
 40  \w   -116.00 -90.00   0.50    0.53    -- -106.00 -61.00 -60.00   52
 41  \w   -144.00 -96.00   0.50    0.53    -- -106.00 -61.00  30.00   96
 42  \w   -155.00-127.00   0.50    0.53    -- -106.00 -79.00  97.89   56
 43  \w   -127.00 -93.00   0.50    0.53    -- -106.00 -46.00 112.49   68
 44  \w   -107.00 -81.00   0.50    0.53    -- -106.00 -81.00 102.80   52
 45  \w   -173.00-148.00   0.50    0.53    -- -106.00 -46.00 112.49   50
 46  \w   -106.00 -81.00   0.50    0.53    -- -106.00 -91.00  43.11   50
 47  \w   -108.00 -83.00   0.50    0.53    -- -106.00 -77.00  90.00   50
 48  \w   -175.00-148.00   0.50    0.53    -- -106.00 -77.00  60.00   54
 49  \w    -66.00 -40.00   0.50    0.53    -- -106.00  61.00 -30.00   52
 50  \w   -173.00-147.00   0.50    0.53    -- -106.00 -51.00 104.15   52
 51  \w   -128.00 -92.00   0.50    0.53    -- -106.00 -51.00 104.15   72
 52  \w   -120.00 -91.00   0.50    0.53    -- -106.00 -61.00   0.00   58
 53  \w   -108.00 -83.00   0.50    0.53    -- -106.00 -77.00 120.00   50
 54  \w   -114.00 -89.00   0.50    0.53    -- -106.00 -65.00  57.04   50
 55  \w   -111.00 -86.00   0.50    0.53    -- -106.00 -69.00  91.99   50
 56  \w   -119.00 -85.00   0.50    0.53    -- -106.00 -74.00  80.27   68
 57  \w   -125.00 -84.00   0.50    0.53    -- -106.00 -79.00  52.97   82
 58  \w   -164.00-129.00   0.50    0.53    -- -106.00 -74.00  80.27   70
 59  \w   -108.00 -83.00   0.50    0.53    -- -106.00 -79.00  97.89   50
 60  \w   -117.00 -91.00   0.50    0.53    -- -106.00 -61.00  90.00   52
 61  \w     79.00 105.00   0.50    0.53    --  107.75 -77.00-120.00   52
 62  \w     40.00  68.00   0.50    0.53    --  107.75 -61.00-180.00   56
 63  \w     98.00 124.00   0.50    0.53    --  107.75  45.00 120.00   52
 64  \w    149.00 175.00   0.50    0.53    --  107.75  30.00 -90.00   52
 65  \w    102.00 128.00   0.50    0.53    --  107.75  30.00 -90.00   52
 66  \w     98.00 124.00   0.50    0.53    --  107.75  45.00-180.00   52
 67  \w     81.00 106.00   0.50    0.53    --  107.75 -94.00-150.00   50
 68  \w     35.00  60.00   0.50    0.53    --  107.75 -61.00  30.00   50
 69  \w    139.00 176.00   0.50    0.53    --  107.75  45.00 120.00   74
 70  \w    102.00 145.00   0.50    0.53    --  107.75  30.00  30.00   86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0405505000
_diffrn_orient_matrix_UB_12      -0.0378052000
_diffrn_orient_matrix_UB_13      0.0560560000
_diffrn_orient_matrix_UB_21      -0.1635228000
_diffrn_orient_matrix_UB_22      -0.0759005000
_diffrn_orient_matrix_UB_23      -0.0184607000
_diffrn_orient_matrix_UB_31      0.1028977000
_diffrn_orient_matrix_UB_32      -0.1353680000
_diffrn_orient_matrix_UB_33      -0.0052807000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            1956
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.974
_diffrn_reflns_theta_min         3.400
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.69a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       plate
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1956
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0197P)^2^+7.5528P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1313
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1873
_reflns_number_total             1956
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00611_si_002.cif
_cod_data_source_block           15444_15.9_pl
_cod_depositor_comments
'Adding full bibliography for 4038260--4038261.cif.'
_cod_database_code               4038260
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C24 H18 N4 O4 '
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.885
_diffrn_oxdiff_digest_frames
;
016b6717ad8fe9f01a1a3ddbcb40c2d55b000622446
;
_diffrn_oxdiff_digest_hkl
;
013abd6add391efd7e4e6e4a6bdb5ae05ffc53
;
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.773(5)
 0.227(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C9(H9), C3(H3), C4(H4), C2(H2)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_shelx_res_checksum              42746
_shelx_hkl_checksum              69214
_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 2.024
_oxdiff_exptl_absorpt_empirical_full_min 0.676