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_1563160
_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 H10 Cl F O2'
_chemical_formula_sum            'C17 H10 Cl F O2'
_chemical_formula_weight         300.70
_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     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-11-11
_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                 92.745(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.82517(17)
_cell_length_b                   19.3273(5)
_cell_length_c                   11.7017(3)
_cell_measurement_reflns_used    10067
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.6510
_cell_measurement_theta_min      4.4090
_cell_volume                     1315.92(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.89a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.89a (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 2018/2 (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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    -95.00 -59.00   1.00    2.00    --  -40.66 -71.00  45.00   36
  2  \w    -38.00 -11.00   1.00    2.00    --  -40.66 -71.00  45.00   27
  3  \w     10.00  69.00   1.00    2.00    --   40.66  71.00 176.00   59
  4  \w    113.00 140.00   1.00    8.00    --  105.15  71.00 176.00   27
  5  \w     76.00 103.00   1.00    8.00    --  105.15  71.00 176.00   27
  6  \w     53.00 121.00   1.00    8.00    --  105.15 -71.00  45.00   68
  7  \w     -3.00  22.00   1.00    2.00    --   34.00  89.00  67.48   25
  8  \w      2.00  27.00   1.00    2.00    --   38.00  88.00 -47.06   25
  9  \w   -114.00 -16.00   1.00    2.00    --  -40.66 -38.00  60.00   98
 10  \w    -70.00  32.00   1.00    2.00    --  -40.66  71.00 176.00  102
 11  \w    -18.00  56.00   1.00    2.00    --   40.66 -71.00  45.00   74
 12  \w     27.00  95.00   1.00    2.00    --   40.66-125.00 -30.00   68
 13  \w     84.00 115.00   1.00    2.00    --   40.66  71.00 176.00   31
 14  \w     13.00  38.00   1.00    2.00    --   46.00  82.00 138.73   25
 15  \w     16.00  41.00   1.00    2.00    --   50.00  82.00  -7.66   25
 16  \w     16.00  41.00   1.00    2.00    --   50.00  81.00  82.71   25
 17  \w     16.00  41.00   1.00    2.00    --   50.00  82.00 -74.34   25
 18  \w     16.00  42.00   1.00    2.00    --   50.00  81.00-178.86   26
 19  \w     26.00  58.00   1.00    2.00    --   58.00  73.00-123.00   32
 20  \w     34.00  64.00   1.00    2.00    --   58.00  71.00 113.05   30
 21  \w     98.00 132.00   1.00    2.00    --   58.00  71.00 113.05   34
 22  \w     39.00 110.00   1.00    2.00    --   66.00  73.00  25.16   71
 23  \w    102.00 127.00   1.00    2.00    --   66.00  72.00  80.97   25
 24  \w     38.00 101.00   1.00    2.00    --   66.00  73.00 -53.00   63
 25  \w     35.00  75.00   1.00    2.00    --   66.00  72.00  80.97   40
 26  \w     38.00 101.00   1.00    2.00    --   70.00  73.00 -83.24   63
 27  \w     38.00  65.00   1.00    2.00    --   70.00  74.00 157.79   27
 28  \w     39.00  73.00   1.00    2.00    --   70.00  73.00  -7.86   34
 29  \w     48.00  93.00   1.00    8.00    --   78.00  69.00-133.62   45
 30  \w     50.00  76.00   1.00    8.00    --   82.00  74.00-164.53   26
 31  \w     52.00  78.00   1.00    8.00    --   82.00  64.00 172.68   26
 32  \w     59.00  85.00   1.00    8.00    --   86.00  52.00 141.36   26
 33  \w     76.00 174.00   1.00    8.00    --  105.15  61.00 -90.00   98
 34  \w     99.00 136.00   1.00    8.00    --  105.15 178.00  60.00   37
 35  \w     76.00 177.00   1.00    8.00    --  105.15  61.00  90.00  101
 36  \w     76.00 106.00   1.00    8.00    --  105.15  61.00  60.00   30
 37  \w     63.00  92.00   1.00    8.00    --  105.15 178.00  60.00   29
 38  \w    120.00 177.00   1.00    8.00    --  105.15  61.00 -60.00   57
 39  \w     29.00 109.00   1.00    8.00    --  105.15-111.00  60.00   80
 40  \w     76.00 104.00   1.00    8.00    --  105.15  61.00 -60.00   28
 41  \w     31.00 109.00   1.00    8.00    --  105.15-111.00-150.00   78
 42  \w     77.00 175.00   1.00    8.00    --  105.15  61.00-150.00   98
 43  \w    121.00 157.00   1.00    8.00    --  105.15  61.00  30.00   36
 44  \w     79.00 119.00   1.00    8.00    --  105.15  61.00 120.00   40
 45  \w     77.00 104.00   1.00    8.00    --  105.15  61.00  30.00   27
 46  \w     64.00 146.00   1.00    8.00    --  105.15 178.00  90.00   82
 47  \w     79.00 162.00   1.00    8.00    --  105.15  61.00 150.00   83
 48  \w    128.00 176.00   1.00    8.00    --  105.15  61.00-120.00   48
 49  \w     76.00 103.00   1.00    8.00    --  105.15  61.00-120.00   27
 50  \w     76.00 145.00   1.00    8.00    --  105.15  61.00 -30.00   69
 51  \w     76.00 165.00   1.00    8.00    --  105.15  61.00   0.00   89
 52  \w     69.00 108.00   1.00    8.00    --  105.15-111.00 -90.00   39
 53  \w    118.00 147.00   1.00    8.00    --  105.15  61.00  60.00   29
 54  \w     34.00 117.00   1.00    8.00    --  105.15 -45.00-180.00   83
;
_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      -0.1389651000
_diffrn_orient_matrix_UB_12      -0.0227323000
_diffrn_orient_matrix_UB_13      0.1022243000
_diffrn_orient_matrix_UB_21      -0.1713934000
_diffrn_orient_matrix_UB_22      0.0594857000
_diffrn_orient_matrix_UB_23      -0.0248949000
_diffrn_orient_matrix_UB_31      -0.1463021000
_diffrn_orient_matrix_UB_32      -0.0479447000
_diffrn_orient_matrix_UB_33      -0.0793946000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_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       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3810
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.602
_diffrn_reflns_theta_min         4.421
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.700
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.405
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.41.89a (Rigaku Oxford Diffraction, 2020)
 Numerical absorption correction based on Gaussian integration over
 a multifaceted crystal model.
 Empirical absorption correction using spherical harmonics
 as implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3810
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0578P)^2^+0.1151P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0903
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3335
_reflns_number_total             3810
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.8479\% 
around [-0.00 1.00 -0.04] (reciprocal) or [-0.02 0.99 -0.10] (direct)
;
_cod_data_source_file            d1sc02583j2.cif
_cod_data_source_block           jft-r292_twin_hklf5
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Gaussian' was
changed to 'gaussian' 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 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1315.92(7)
_cod_database_code               1563160
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C17 H10 Cl F O2'
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.442
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.4948(15)
 0.5052(15)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_shelx_res_checksum              52679
_shelx_hkl_checksum              58440
_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 1.778
_oxdiff_exptl_absorpt_empirical_full_min 0.539
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2