2,6-Dicyano-4-pyrone as a Novel and Multifarious Building Block for the Synthesis of 2,6-Bis(hetaryl)-4-pyrones and 2,6-Bis(hetaryl)-4-pyridinols
Obydennov, Dmitrii L.; Simbirtseva, Alena E.; Piksin, Sergey E.; Sosnovskikh, Vyacheslav Y.; ACS Omega 5 (2020) 33406–33420; doi:10.1021/acsomega.0c05357

data_4518324
_publ_section_title
;
 2,6-Dicyano-4-pyrone as a Novel and Multifarious Building Block for the
 Synthesis of 2,6-Bis(hetaryl)-4-pyrones and 2,6-Bis(hetaryl)-4-pyridinols
;
_journal_issue                   51
_journal_name_full               'ACS Omega'
_journal_page_first              33406
_journal_page_last               33420
_journal_paper_doi               10.1021/acsomega.0c05357
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C11 H8 N4 O4'
_chemical_formula_sum            'C11 H8 N4 O4'
_chemical_formula_weight         260.21
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-11-18
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.360(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4140(14)
_cell_length_b                   10.9106(9)
_cell_length_c                   9.0833(11)
_cell_measurement_reflns_used    1378
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.1410
_cell_measurement_theta_min      4.1420
_cell_volume                     1112.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.961
_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    -29.00  61.00   1.00   65.00    --   22.05 -95.00  82.00   90
  2  \w    -23.00  26.00   1.00   65.00    --  -23.77  95.00-168.00   49
  3  \w    -57.00 -31.00   1.00   65.00    --  -23.77  95.00-168.00   26
  4  \w     32.00  99.00   1.00   65.00    --   22.05-178.00   0.00   67
  5  \w     -6.00  92.00   1.00   65.00    --   22.05  77.00   0.00   98
  6  \w    -17.00   8.00   1.00   65.00    --   22.05  95.00-168.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0335365000
_diffrn_orient_matrix_UB_12      -0.0443645000
_diffrn_orient_matrix_UB_13      0.0316618000
_diffrn_orient_matrix_UB_21      -0.0488294000
_diffrn_orient_matrix_UB_22      0.0411171000
_diffrn_orient_matrix_UB_23      -0.0076978000
_diffrn_orient_matrix_UB_31      -0.0219433000
_diffrn_orient_matrix_UB_32      -0.0237314000
_diffrn_orient_matrix_UB_33      -0.0724379000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8120
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.120
_diffrn_reflns_theta_min         3.629
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light brown'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       prism
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0704
_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^)+(0.1010P)^2^+0.0500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1705
_refine_ls_wR_factor_ref         0.2384
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1442
_reflns_number_total             2882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c05357_si_002.cif
_cod_data_source_block           exp_633
_cod_depositor_comments          'Adding full bibliography for 4518324.cif.'
_cod_database_code               4518324
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.948
_reflns_odcompleteness_completeness 99.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.22
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_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 2.870
_oxdiff_exptl_absorpt_empirical_full_min 0.526