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_1563159
_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         'C18 H21 N3 O2'
_chemical_formula_sum            'C18 H21 N3 O2'
_chemical_formula_weight         311.38
_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             2020-12-08
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-04-06 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.1940(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.40586(17)
_cell_length_b                   28.8016(4)
_cell_length_c                   11.4833(2)
_cell_measurement_reflns_used    10150
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.6240
_cell_measurement_theta_min      4.7430
_cell_volume                     3250.29(10)
_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 5.2817
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_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    -66.00  12.00   1.00    5.00    --  -40.91  98.00-118.00   78
  2  \w     20.00  79.00   1.00    5.00    --   40.91 -98.00 134.00   59
  3  \w    114.00 161.00   1.00   20.00    --  105.15  98.00-118.00   47
  4  \w     56.00 107.00   1.00   20.00    --  105.15 -98.00 134.00   51
  5  \w      4.00  31.00   1.00    5.00    --  -40.91  38.00  30.00   27
  6  \w    -42.00 -16.00   1.00    5.00    --  -40.91  38.00  30.00   26
  7  \w   -111.00 -16.00   1.00    5.00    --  -40.91 -38.00  90.00   95
  8  \w   -113.00 -17.00   1.00    5.00    --  -40.91 -57.00   0.00   96
  9  \w     88.00 113.00   1.00    5.00    --   40.91  57.00  30.00   25
 10  \w     52.00 105.00   1.00   20.00    --  105.15 -94.00-150.00   53
 11  \w    108.00 133.00   1.00   20.00    --  105.15 -61.00 120.00   25
 12  \w     28.00 105.00   1.00   20.00    --  105.15 -94.00 -60.00   77
 13  \w     33.00  87.00   1.00   20.00    --  105.15 -61.00 120.00   54
 14  \w     26.00  72.00   1.00   20.00    --  105.15 -94.00  30.00   46
 15  \w    104.00 177.00   1.00   20.00    --  105.15 111.00-180.00   73
 16  \w    103.00 154.00   1.00   20.00    --  105.15  77.00 -30.00   51
 17  \w    105.00 134.00   1.00   20.00    --  105.15 111.00 -30.00   29
 18  \w     37.00  63.00   1.00   20.00    --  105.15-111.00 -60.00   26
 19  \w     84.00 109.00   1.00   20.00    --  105.15-111.00 -30.00   25
 20  \w    105.00 174.00   1.00   20.00    --  105.15 111.00-150.00   69
 21  \w     80.00 178.00   1.00   20.00    --  105.15  45.00 -60.00   98
 22  \w     43.00 133.00   1.00   20.00    --  105.15 -30.00 120.00   90
 23  \w     72.00 109.00   1.00   20.00    --  105.15-111.00  60.00   37
 24  \w     34.00 129.00   1.00   20.00    --  105.15 -45.00 -90.00   95
;
_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      -0.0280882000
_diffrn_orient_matrix_UB_12      -0.0500528000
_diffrn_orient_matrix_UB_13      0.0323177000
_diffrn_orient_matrix_UB_21      -0.0992574000
_diffrn_orient_matrix_UB_22      -0.0067633000
_diffrn_orient_matrix_UB_23      -0.1319995000
_diffrn_orient_matrix_UB_31      0.1180218000
_diffrn_orient_matrix_UB_32      -0.0176191000
_diffrn_orient_matrix_UB_33      -0.0413341000
_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     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8186
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.781
_diffrn_reflns_theta_min         3.069
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.600
_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    1.273
_exptl_crystal_description       prism
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.431
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0017(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   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     586
_refine_ls_number_reflns         8186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0856P)^2^+0.0670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1136
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7212
_reflns_number_total             8186
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by -179.9244\% 
around [0.00 -0.00 1.00] (reciprocal) or [0.34 -0.00 0.94] (direct)
Component 3 rotated by 178.8065\% 
around [-0.01 1.00 0.07] (reciprocal) or [0.11 0.90 0.42] (direct)
;
_cod_data_source_file            d1sc02583j2.cif
_cod_data_source_block           jft-r348
_cod_database_code               1563159
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C18 H21 N3 O2'
_shelx_estimated_absorpt_t_max   0.940
_shelx_estimated_absorpt_t_min   0.758
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5832(16)
 0.3779(13) 0.0389(9)
;
_shelx_res_checksum              24588
_shelx_hkl_checksum              78365
_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 2.730
_oxdiff_exptl_absorpt_empirical_full_min 0.291
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               3