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_1563157
_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         'C23 H25 N3 O2'
_chemical_formula_sum            'C23 H25 N3 O2'
_chemical_formula_weight         375.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-11-02
_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                 96.950(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4016(3)
_cell_length_b                   9.5092(2)
_cell_length_c                   19.0932(4)
_cell_measurement_reflns_used    5393
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      76.4150
_cell_measurement_theta_min      3.8580
_cell_volume                     2054.88(8)
_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 0.989
_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   -116.00 -13.00   1.00    1.00    --  -43.01 -66.00-138.00  103
  2  \w    -62.00  23.00   1.00    1.00    --  -43.01  66.00  -3.00   85
  3  \w     93.00 177.00   1.00    4.00    --  112.00  66.00  -3.00   84
  4  \w     39.00 102.00   1.00    4.00    --  112.00 -66.00-138.00   63
  5  \w     47.00  84.00   1.00    1.00    --   43.01-125.00 150.00   37
  6  \w     21.00  77.00   1.00    1.00    --   43.01 -99.00  60.00   56
  7  \w    104.00 145.00   1.00    4.00    --  112.00  77.00 -60.00   41
  8  \w    144.00 176.00   1.00    4.00    --  112.00  77.00-120.00   32
  9  \w    109.00 135.00   1.00    4.00    --  112.00  30.00 -30.00   26
 10  \w    146.00 175.00   1.00    4.00    --  112.00  30.00 -30.00   29
 11  \w    125.00 160.00   1.00    4.00    --  112.00 111.00-150.00   35
 12  \w     40.00 109.00   1.00    4.00    --  112.00-111.00-120.00   69
 13  \w     39.00 108.00   1.00    4.00    --  112.00-111.00-150.00   69
 14  \w     41.00 127.00   1.00    4.00    --  112.00 -61.00 -90.00   86
 15  \w    123.00 175.00   1.00    4.00    --  112.00 111.00-180.00   52
 16  \w    131.00 156.00   1.00    4.00    --  112.00  77.00-180.00   25
 17  \w    104.00 176.00   1.00    4.00    --  112.00  77.00 -90.00   72
;
_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      0.0417568000
_diffrn_orient_matrix_UB_12      -0.0397535000
_diffrn_orient_matrix_UB_13      -0.0712166000
_diffrn_orient_matrix_UB_21      -0.0783598000
_diffrn_orient_matrix_UB_22      0.1167764000
_diffrn_orient_matrix_UB_23      -0.0367277000
_diffrn_orient_matrix_UB_31      0.1031231000
_diffrn_orient_matrix_UB_32      0.1049614000
_diffrn_orient_matrix_UB_33      0.0138737000
_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  0.0226
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11847
_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         76.556
_diffrn_reflns_theta_min         3.906
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.530
_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 intense yellow'
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.254
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4260
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0452
_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^)+(0.0880P)^2^+0.2554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1321
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3775
_reflns_number_total             4260
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02583j2.cif
_cod_data_source_block           r232
_cod_original_cell_volume        2054.86(9)
_cod_database_code               1563157
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C23 H25 N3 O2'
_shelx_estimated_absorpt_t_max   0.857
_shelx_estimated_absorpt_t_min   0.787
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C25-C21 \\sim C24-C21 \\sim C21-C22 \\sim C23-C21
 with sigma of 0.02
 C25-C23 \\sim C24-C22
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C21 \\sim C22 \\sim C23 \\sim C24 \\sim C25: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 C22, C21, C23, C24, C25
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H21A)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C24)=Sof(H24A)=Sof(H24B)=
 Sof(H24C)=1-FVAR(1)
 Sof(H21)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C25)=Sof(H25A)=Sof(H25B)=
 Sof(H25C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C21(H21A), C21(H21)
6.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C)
;
_shelx_res_checksum              16196
_shelx_hkl_checksum              83120
_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 1.974
_oxdiff_exptl_absorpt_empirical_full_min 0.618