Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl triazenes from alkynyl triazenes
Tan, Jin-Fay; Bormann, Carl Thomas; Severin, Kay; Cramer, Nicolai; Chemical Science  (2022) –; doi:10.1039/D2SC00294A

data_1566363
_publ_section_title
;
 Chemo- and regio-divergent access to fluorinated 1-alkyl and 1-acyl
 triazenes from alkynyl triazenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00294A
_journal_year                    2022
_chemical_formula_moiety         'C18 H21 F4 N3'
_chemical_formula_sum            'C18 H21 F4 N3'
_chemical_formula_weight         355.38
_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   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-07-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2022-01-13 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.4811(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.21581(8)
_cell_length_b                   14.44752(14)
_cell_length_c                   13.23644(14)
_cell_measurement_reflns_used    11336
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      75.5750
_cell_measurement_theta_min      3.0440
_cell_volume                     1761.78(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.76a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.76a (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 1.000
_diffrn_measured_fraction_theta_max 0.994
_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    -72.00  33.00   1.00    1.00    --  -40.91  72.00-145.00  105
  2  \w    -98.00 -19.00   1.00    1.00    --  -40.91 -72.00  84.00   79
  3  \w     38.00  63.00   1.00    1.00    --   40.91  72.00-145.00   25
  4  \w     -5.00  20.00   1.00    1.00    --   40.91 -72.00  84.00   25
  5  \w     51.00  92.00   1.00    4.00    --  112.00 -72.00  84.00   41
  6  \w    131.00 158.00   1.00    4.00    --  112.00  72.00-145.00   27
  7  \w      7.00  32.00   1.00    1.00    --  -40.91  57.00   0.00   25
  8  \w     20.00 113.00   1.00    1.00    --   40.91  38.00 -30.00   93
  9  \w     42.00  97.00   1.00    1.00    --   40.91-125.00   0.00   55
 10  \w    -31.00  63.00   1.00    1.00    --   40.91 -38.00 -30.00   94
 11  \w     43.00  89.00   1.00    4.00    --  112.00-111.00  60.00   46
 12  \w     98.00 178.00   1.00    4.00    --  112.00  45.00 -30.00   80
 13  \w    103.00 178.00   1.00    4.00    --  112.00  77.00-180.00   75
 14  \w     71.00 108.00   1.00    4.00    --  112.00-111.00 -90.00   37
 15  \w    107.00 139.00   1.00    4.00    --  112.00 111.00  60.00   32
 16  \w    149.00 175.00   1.00    4.00    --  112.00 111.00  60.00   26
 17  \w    127.00 165.00   1.00    4.00    --  112.00  30.00  30.00   38
 18  \w     53.00 109.00   1.00    4.00    --  112.00-111.00  90.00   56
 19  \w     84.00 111.00   1.00    4.00    --  112.00  61.00  90.00   27
 20  \w     42.00 108.00   1.00    4.00    --  112.00-111.00-150.00   66
 21  \w     78.00 103.00   1.00    4.00    --  112.00-111.00 150.00   25
 22  \w     53.00  94.00   1.00    4.00    --  112.00-111.00   0.00   41
 23  \w    101.00 177.00   1.00    4.00    --  112.00  61.00-120.00   76
 24  \w     36.00 109.00   1.00    4.00    --  112.00-111.00-180.00   73
 25  \w     36.00  68.00   1.00    4.00    --  112.00-111.00 150.00   32
 26  \w     36.00  61.00   1.00    4.00    --  112.00 -94.00  30.00   25
 27  \w     82.00 109.00   1.00    4.00    --  112.00-111.00 120.00   27
 28  \w     86.00 113.00   1.00    4.00    --  112.00  30.00  30.00   27
 29  \w     37.00  88.00   1.00    4.00    --  112.00-111.00 -60.00   51
 30  \w     68.00 109.00   1.00    4.00    --  112.00-111.00 -30.00   41
 31  \w     63.00 135.00   1.00    4.00    --  112.00 178.00 -30.00   72
 32  \w     83.00 171.00   1.00    4.00    --  112.00  61.00 -60.00   88
 33  \w    113.00 155.00   1.00    4.00    --  112.00  30.00 -60.00   42
 34  \w    119.00 146.00   1.00    4.00    --  112.00  61.00  90.00   27
 35  \w     36.00  63.00   1.00    4.00    --  112.00-111.00-120.00   27
 36  \w     69.00 108.00   1.00    4.00    --  112.00-111.00  30.00   39
 37  \w     66.00 118.00   1.00    4.00    --  112.00 178.00  90.00   52
;
_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      -0.0888151000
_diffrn_orient_matrix_UB_12      -0.0738516000
_diffrn_orient_matrix_UB_13      -0.0583107000
_diffrn_orient_matrix_UB_21      0.0435588000
_diffrn_orient_matrix_UB_22      0.0441369000
_diffrn_orient_matrix_UB_23      -0.1007951000
_diffrn_orient_matrix_UB_31      0.1349445000
_diffrn_orient_matrix_UB_32      -0.0628288000
_diffrn_orient_matrix_UB_33      -0.0020951000
_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  0.0214
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18746
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.037
_diffrn_reflns_theta_min         4.531
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.941
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.399
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.41.76a (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    1.340
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.358
_exptl_crystal_size_mid          0.247
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3665
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0630P)^2^+0.3431P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1065
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3433
_reflns_number_total             3665
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00294a2.cif
_cod_data_source_block           jft-01-537
_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        1761.79(3)
_cod_database_code               1566363
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C18 H21 F4 N3'
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.729
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C)
;
_shelx_res_checksum              92404
_shelx_hkl_checksum              90765
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.841
_oxdiff_exptl_absorpt_empirical_full_min 0.564