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_1563161
_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         'C20 H25 N3 O2'
_chemical_formula_sum            'C20 H25 N3 O2'
_chemical_formula_weight         339.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-12-10
_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                109.270(6)
_cell_angle_beta                 97.031(5)
_cell_angle_gamma                111.857(6)
_cell_formula_units_Z            4
_cell_length_a                   10.4488(6)
_cell_length_b                   13.1778(8)
_cell_length_c                   15.6415(10)
_cell_measurement_reflns_used    3996
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      71.6530
_cell_measurement_theta_min      3.0840
_cell_volume                     1811.5(2)
_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 0.998
_diffrn_measured_fraction_theta_max 0.971
_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    -60.00 -15.00   1.00    1.50    --  -43.01  95.00-174.00   45
  2  \w     23.00  69.00   1.00    1.50    --   43.01 -95.00  75.00   46
  3  \w     60.00 106.00   1.00    6.00    --  103.80 -95.00  75.00   46
  4  \w    104.00 171.00   1.00    6.00    --  103.80  95.00-174.00   67
  5  \w   -105.00 -17.00   1.00    1.50    --  -43.01 -57.00-120.00   88
  6  \w    -79.00  -8.00   1.00    1.50    --  -43.01 125.00  60.00   71
  7  \w   -112.00 -20.00   1.00    1.50    --  -43.01 -57.00   0.00   92
  8  \w     19.00 100.00   1.00    1.50    --   43.01  37.00   0.00   81
  9  \w     76.00 168.00   1.00    6.00    --  103.80  30.00-180.00   92
 10  \w     30.00  57.00   1.00    6.00    --  103.80-111.00-120.00   27
 11  \w    103.00 176.00   1.00    6.00    --  103.80  77.00-120.00   73
 12  \w     29.00 108.00   1.00    6.00    --  103.80-111.00 -30.00   79
 13  \w     37.00 106.00   1.00    6.00    --  103.80-111.00  60.00   69
 14  \w     76.00 103.00   1.00    6.00    --  103.80  30.00 120.00   27
 15  \w    116.00 176.00   1.00    6.00    --  103.80  30.00 120.00   60
 16  \w    141.00 166.00   1.00    6.00    --  103.80 111.00-120.00   25
 17  \w     42.00  95.00   1.00    6.00    --  103.80-111.00-180.00   53
 18  \w     67.00 108.00   1.00    6.00    --  103.80-111.00-120.00   41
 19  \w     73.00 124.00   1.00    6.00    --  103.80 178.00  90.00   51
 20  \w     55.00 130.00   1.00    6.00    --  103.80 -45.00 120.00   75
 21  \w    108.00 168.00   1.00    6.00    --  103.80 111.00  30.00   60
 22  \w    129.00 178.00   1.00    6.00    --  103.80  77.00  90.00   49
;
_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      0.0577797000
_diffrn_orient_matrix_UB_12      0.1331357000
_diffrn_orient_matrix_UB_13      0.0661456000
_diffrn_orient_matrix_UB_21      -0.0813410000
_diffrn_orient_matrix_UB_22      0.0198889000
_diffrn_orient_matrix_UB_23      -0.0772177000
_diffrn_orient_matrix_UB_31      -0.1320102000
_diffrn_orient_matrix_UB_32      -0.0301497000
_diffrn_orient_matrix_UB_33      0.0383940000
_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  0.0446
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15128
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.679
_diffrn_reflns_theta_min         3.118
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.664
_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 light yellow'
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       irregular
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.122
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     648
_refine_ls_number_reflns         7000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0654
_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^)+(0.0917P)^2^+0.5831P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5303
_reflns_number_total             7000
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02583j2.cif
_cod_data_source_block           jft-r352
_cod_database_code               1563161
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C20 H25 N3 O2'
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.862
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
;
_shelx_res_checksum              57762
_shelx_hkl_checksum              33295
_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 2.437
_oxdiff_exptl_absorpt_empirical_full_min 0.654