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_1563163
_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 H11 Cl O2'
_chemical_formula_sum            'C17 H11 Cl O2'
_chemical_formula_weight         282.71
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-02-23
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-04-06 deposited with the CCDC.	2021-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                83.587(2)
_cell_angle_beta                 81.245(3)
_cell_angle_gamma                85.103(3)
_cell_formula_units_Z            4
_cell_length_a                   7.9105(3)
_cell_length_b                   9.8857(3)
_cell_length_c                   17.5630(4)
_cell_measurement_reflns_used    5533
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      72.3910
_cell_measurement_theta_min      4.9550
_cell_volume                     1345.67(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (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 0.996
_diffrn_measured_fraction_theta_max 0.970
_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    -65.00  30.00   1.00    3.00    --  -40.91  34.00 154.00   95
  2  \w    -89.00 -42.00   1.00    3.00    --  -40.91 -34.00  -3.00   47
  3  \w     -8.00  17.00   1.00    3.00    --   40.91 -34.00  -3.00   25
  4  \w     42.00  67.00   1.00    3.00    --   40.91  34.00 154.00   25
  5  \w     31.00 128.00   1.00   12.00    --  105.15 -34.00  -3.00   97
  6  \w    105.00 142.00   1.00   12.00    --  105.15  34.00 154.00   37
  7  \w    -78.00  -6.00   1.00    3.00    --  -40.91 125.00-180.00   72
  8  \w     44.00  71.00   1.00    3.00    --   40.91-125.00-180.00   27
  9  \w     27.00  67.00   1.00    3.00    --   40.91-125.00 -60.00   40
 10  \w     46.00  95.00   1.00    3.00    --   40.91-125.00  30.00   49
 11  \w     16.00 115.00   1.00    3.00    --   40.91  38.00   0.00   99
 12  \w     31.00  58.00   1.00   12.00    --  105.15-111.00-180.00   27
 13  \w    104.00 162.00   1.00   12.00    --  105.15  77.00   0.00   58
 14  \w     43.00 134.00   1.00   12.00    --  105.15 -61.00  90.00   91
 15  \w    111.00 178.00   1.00   12.00    --  105.15  77.00  30.00   67
 16  \w    140.00 170.00   1.00   12.00    --  105.15 111.00  90.00   30
 17  \w    120.00 176.00   1.00   12.00    --  105.15  77.00 150.00   56
 18  \w     30.00 107.00   1.00   12.00    --  105.15-111.00  30.00   77
 19  \w     55.00 107.00   1.00   12.00    --  105.15-111.00  90.00   52
 20  \w     68.00 105.00   1.00   12.00    --  105.15-111.00 -60.00   37
 21  \w     89.00 176.00   1.00   12.00    --  105.15  45.00 -30.00   87
 22  \w     80.00 109.00   1.00   12.00    --  105.15-111.00-180.00   29
 23  \w    115.00 178.00   1.00   12.00    --  105.15  77.00  60.00   63
 24  \w     45.00  90.00   1.00   12.00    --  105.15 -94.00-120.00   45
;
_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      -0.0635383000
_diffrn_orient_matrix_UB_12      -0.1391484000
_diffrn_orient_matrix_UB_13      -0.0099117000
_diffrn_orient_matrix_UB_21      0.1819910000
_diffrn_orient_matrix_UB_22      -0.0472312000
_diffrn_orient_matrix_UB_23      -0.0365385000
_diffrn_orient_matrix_UB_31      0.0430999000
_diffrn_orient_matrix_UB_32      -0.0558456000
_diffrn_orient_matrix_UB_33      0.0807669000
_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  0.0232
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10445
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.527
_diffrn_reflns_theta_min         4.512
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.492
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.482
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.93a (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    1.395
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0347
_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^)+(0.0516P)^2^+0.1922P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0888
_refine_ls_wR_factor_ref         0.0938
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4471
_reflns_number_total             5170
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02583j2.cif
_cod_data_source_block           jft-r386
_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        1345.68(8)
_cod_database_code               1563163
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C17 H11 Cl O2'
_shelx_estimated_absorpt_t_max   0.929
_shelx_estimated_absorpt_t_min   0.623
_reflns_odcompleteness_completeness 99.69
_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),
 C15(H15), C16(H16), C17(H17), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27),
  C28(H28), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34)
;
_shelx_res_checksum              30829
_shelx_hkl_checksum              89461
_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 1.976
_oxdiff_exptl_absorpt_empirical_full_min 0.505