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_1563162
_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 F2 O2'
_chemical_formula_sum            'C17 H10 F2 O2'
_chemical_formula_weight         284.25
_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             2020-11-26
_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                 97.2906(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.16235(12)
_cell_length_b                   18.5749(4)
_cell_length_c                   11.4059(2)
_cell_measurement_reflns_used    6933
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.6310
_cell_measurement_theta_min      4.5290
_cell_volume                     1295.02(4)
_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 10.2665
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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   -114.00 -89.00   1.00    1.00    --  -43.13-143.00 -19.00   25
  2  \w    -87.00 -13.00   1.00    1.00    --  -43.13 127.00-133.00   74
  3  \w    -78.00 -53.00   1.00    1.00    --  -43.13 143.00  36.00   25
  4  \w     49.00  74.00   1.00    1.00    --   43.13-143.00 -19.00   25
  5  \w     64.00  89.00   1.00    1.00    --   43.13-127.00 150.00   25
  6  \w     60.00 114.00   1.00    4.00    --  103.80-127.00 150.00   54
  7  \w    105.00 130.00   1.00    4.00    --  103.80 143.00  36.00   25
  8  \w    112.00 137.00   1.00    4.00    --  103.80 127.00-133.00   25
  9  \w     72.00 107.00   1.00    4.00    --  103.80-143.00 -19.00   35
 10  \w   -102.00 -20.00   1.00    1.00    --  -43.13 -37.00  30.00   82
 11  \w   -122.00 -12.00   1.00    1.00    --  -43.13 -19.00 120.00  110
 12  \w     12.00  40.00   1.00    1.00    --   43.13  81.00  23.21   28
 13  \w     46.00 129.00   1.00    4.00    --  103.80 -45.00 120.00   83
 14  \w     43.00  69.00   1.00    4.00    --  103.80 -77.00 -60.00   26
 15  \w     22.00 106.00   1.00    4.00    --  103.80 -94.00 150.00   84
 16  \w     67.00  92.00   1.00    4.00    --  103.80 178.00 -30.00   25
 17  \w    104.00 170.00   1.00    4.00    --  103.80  77.00  90.00   66
 18  \w    104.00 131.00   1.00    4.00    --  103.80  77.00-180.00   27
 19  \w    113.00 144.00   1.00    4.00    --  103.80 178.00 -30.00   31
 20  \w     28.00  83.00   1.00    4.00    --  103.80-111.00  60.00   55
 21  \w     77.00 150.00   1.00    4.00    --  103.80  30.00  90.00   73
 22  \w    104.00 130.00   1.00    4.00    --  103.80  77.00-120.00   26
 23  \w    149.00 174.00   1.00    4.00    --  103.80  77.00-120.00   25
 24  \w    116.00 177.00   1.00    4.00    --  103.80 111.00 120.00   61
 25  \w     28.00 108.00   1.00    4.00    --  103.80-111.00 -30.00   80
 26  \w     51.00 108.00   1.00    4.00    --  103.80-111.00  90.00   57
 27  \w     78.00 173.00   1.00    4.00    --  103.80  30.00-180.00   95
;
_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      0.0397285000
_diffrn_orient_matrix_UB_12      -0.0817994000
_diffrn_orient_matrix_UB_13      -0.0034888000
_diffrn_orient_matrix_UB_21      -0.1947620000
_diffrn_orient_matrix_UB_22      -0.0126400000
_diffrn_orient_matrix_UB_23      0.0698771000
_diffrn_orient_matrix_UB_31      -0.1549109000
_diffrn_orient_matrix_UB_32      -0.0050878000
_diffrn_orient_matrix_UB_33      -0.1168555000
_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  0.0220
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11023
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.568
_diffrn_reflns_theta_min         4.576
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.340
_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    1.458
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0015(3)
_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   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0348P)^2^+0.3304P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0784
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2298
_reflns_number_total             2543
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02583j2.cif
_cod_data_source_block           jft-r318
_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        1295.03(4)
_cod_database_code               1563162
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C17 H10 F2 O2'
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.710
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C16(H16), C17(H17)
;
_shelx_res_checksum              18339
_shelx_hkl_checksum              79233
_olex2_date_sample_data_collection 2020-11-26
_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 1.520
_oxdiff_exptl_absorpt_empirical_full_min 0.668