Alkynyl Triazenes Enable Divergent Syntheses of 2-Pyrones
Tan, Jin-Fay; Bormann, Carl Thomas; Severin, Kay; Cramer, Nicolai; Chemical Science  (2021) –; doi:10.1039/D1SC02583J

data_1563158
_publ_section_title
;
 Alkynyl Triazenes Enable Divergent Syntheses of 2-Pyrones
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02583J
_journal_year                    2021
_chemical_formula_moiety         'C17 H11 F O2'
_chemical_formula_sum            'C17 H11 F O2'
_chemical_formula_weight         266.26
_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   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-11-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-04-06 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.117(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.12164(16)
_cell_length_b                   18.5825(5)
_cell_length_c                   11.3690(2)
_cell_measurement_reflns_used    6150
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      76.5240
_cell_measurement_theta_min      4.5500
_cell_volume                     1283.32(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_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    -98.00 -49.00   1.00    1.50    --  -43.01-165.00 -21.00   49
  2  \w    -84.00 -37.00   1.00    1.50    --  -43.01 116.00-145.00   47
  3  \w    -95.00 -70.00   1.00    1.50    --  -43.01 165.00   2.00   25
  4  \w     33.00  58.00   1.00    1.50    --   43.01-116.00 126.00   25
  5  \w     92.00 124.00   1.00    1.50    --   43.01-165.00 -21.00   32
  6  \w     73.00  98.00   1.00    6.00    --  112.00-116.00 126.00   25
  7  \w     76.00 101.00   1.00    6.00    --  112.00-165.00 -21.00   25
  8  \w     89.00 114.00   1.00    6.00    --  112.00 165.00   2.00   25
  9  \w    104.00 139.00   1.00    6.00    --  112.00 116.00-145.00   35
 10  \w    -53.00 -19.00   1.00    1.50    --  -43.01 -37.00 -60.00   34
 11  \w   -115.00 -58.00   1.00    1.50    --  -43.01 -37.00 -60.00   57
 12  \w    -31.00  67.00   1.00    1.50    --   43.01 -37.00-180.00   98
 13  \w     16.00  60.00   1.00    1.50    --   43.01 -37.00 -30.00   44
 14  \w    -21.00   4.00   1.00    1.50    --   43.01 -37.00 -30.00   25
 15  \w     13.00  66.00   1.00    1.50    --   43.01 -99.00 150.00   53
 16  \w    137.00 163.00   1.00    6.00    --  112.00 111.00-180.00   26
 17  \w     36.00 109.00   1.00    6.00    --  112.00-111.00 150.00   73
 18  \w    153.00 178.00   1.00    6.00    --  112.00  61.00-180.00   25
 19  \w    109.00 175.00   1.00    6.00    --  112.00  77.00  60.00   66
 20  \w     62.00 101.00   1.00    6.00    --  112.00-111.00 -60.00   39
 21  \w     69.00 109.00   1.00    6.00    --  112.00-111.00-150.00   40
 22  \w     32.00  67.00   1.00    6.00    --  112.00 -94.00 120.00   35
 23  \w     63.00  96.00   1.00    6.00    --  112.00-111.00 -30.00   33
 24  \w    109.00 178.00   1.00    6.00    --  112.00 111.00 -90.00   69
 25  \w     30.00  64.00   1.00    6.00    --  112.00 -94.00 -30.00   34
 26  \w     98.00 174.00   1.00    6.00    --  112.00  45.00  30.00   76
 27  \w     59.00  85.00   1.00    6.00    --  112.00-111.00  60.00   26
 28  \w    104.00 171.00   1.00    6.00    --  112.00 111.00 120.00   67
 29  \w    107.00 177.00   1.00    6.00    --  112.00  45.00   0.00   70
 30  \w     39.00 106.00   1.00    6.00    --  112.00 -45.00 120.00   67
 31  \w     73.00  99.00   1.00    6.00    --  112.00-111.00-120.00   26
 32  \w    110.00 150.00   1.00    6.00    --  112.00  77.00 -90.00   40
 33  \w     46.00 109.00   1.00    6.00    --  112.00-111.00   0.00   63
 34  \w     37.00  62.00   1.00    6.00    --  112.00-111.00  90.00   25
 35  \w     65.00 106.00   1.00    6.00    --  112.00-111.00  90.00   41
 36  \w    103.00 128.00   1.00    6.00    --  112.00  61.00-180.00   25
 37  \w     82.00 107.00   1.00    6.00    --  112.00 -94.00 120.00   25
 38  \w     77.00 108.00   1.00    6.00    --  112.00-111.00  30.00   31
 39  \w     42.00 109.00   1.00    6.00    --  112.00-111.00 -90.00   67
 40  \w    125.00 165.00   1.00    6.00    --  112.00 111.00 150.00   40
 41  \w    106.00 152.00   1.00    6.00    --  112.00  77.00 120.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0145070000
_diffrn_orient_matrix_UB_12      -0.0808125000
_diffrn_orient_matrix_UB_13      0.0283651000
_diffrn_orient_matrix_UB_21      -0.2124182000
_diffrn_orient_matrix_UB_22      0.0136544000
_diffrn_orient_matrix_UB_23      0.0563713000
_diffrn_orient_matrix_UB_31      -0.1377147000
_diffrn_orient_matrix_UB_32      -0.0125896000
_diffrn_orient_matrix_UB_33      -0.1211002000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14068
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.661
_diffrn_reflns_theta_min         4.585
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.503
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.609
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.083
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0020(4)
_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   1.035
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0328
_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^)+(0.0524P)^2^+0.1936P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2402
_reflns_number_total             2685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02583j2.cif
_cod_data_source_block           jft-r263
_cod_original_cell_volume        1283.32(6)
_cod_database_code               1563158
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H11 O2 F1'
_shelx_estimated_absorpt_t_max   0.935
_shelx_estimated_absorpt_t_min   0.634
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
;
_shelx_res_checksum              28481
_shelx_hkl_checksum              85629
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.092
_oxdiff_exptl_absorpt_empirical_full_min 0.679