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_1566364
_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         'C15 H21 F2 N3 O'
_chemical_formula_sum            'C15 H21 F2 N3 O'
_chemical_formula_weight         297.35
_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             2021-07-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2022-01-13 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                104.216(2)
_cell_angle_beta                 114.117(2)
_cell_angle_gamma                101.164(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5957(2)
_cell_length_b                   9.9111(3)
_cell_length_c                   10.2433(2)
_cell_measurement_reflns_used    8522
_cell_measurement_temperature    140.00(10)
_cell_measurement_theta_max      74.4200
_cell_measurement_theta_min      4.8760
_cell_volume                     812.95(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.976
_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     44.00  88.00   0.50    0.50    --   65.75  15.00 120.00   88
  2  \w     49.00  88.00   0.50    1.00    --   76.97  15.00  90.00   78
  3  \w     54.00 108.00   0.50    1.00    --   76.97  15.00  30.00  108
  4  \w     67.00  93.00   0.50    1.00    --   76.97  15.00 -30.00   52
  5  \w     65.00 110.00   0.50    1.00    --   76.97   0.00 -90.00   90
  6  \w     40.00 106.00   0.50    0.50    --   65.75  15.00-120.00  132
  7  \w     39.00 100.00   0.50    0.50    --   65.75   0.00-150.00  122
  8  \w     53.00 117.00   0.50    1.00    --   76.97  15.00-180.00  128
  9  \w     39.00  86.00   0.50    0.50    --   65.75   0.00 -90.00   94
 10  \w     43.00  97.00   0.50    0.50    --   65.75   0.00 -30.00  108
 11  \w     49.00 108.00   0.50    1.00    --   76.97   0.00 -30.00  118
 12  \w     40.00  91.00   0.50    1.00    --   76.97-111.00  77.00  102
 13  \w     52.00  93.00   0.50    1.00    --   76.97-125.00 150.00   82
 14  \w     73.00  98.00   0.50    0.50    --   73.19-125.00 120.00   50
 15  \w     55.00 102.00   0.50    1.00    --   76.97-125.00  60.00   94
 16  \w     42.00  71.00   0.50    1.00    --   76.97-125.00  30.00   58
 17  \w     36.00 101.00   0.50    1.00    --   76.97-125.00 -30.00  130
 18  \w     31.00  63.00   0.50    0.50    --   65.75-125.00 -60.00   64
 19  \w     52.00 102.00   0.50    1.00    --   76.97-125.00   0.00  100
 20  \w     42.00 100.00   0.50    1.00    --   76.97-125.00 -60.00  116
 21  \w     37.00 101.00   0.50    1.00    --   76.97-125.00 -90.00  128
 22  \w     36.00 101.00   0.50    1.00    --   76.97-125.00-150.00  130
 23  \w     49.00 102.00   0.50    1.00    --   76.97-125.00-180.00  106
 24  \w     71.00 102.00   0.50    1.00    --   76.97-125.00-120.00   62
 25  \w     41.00  66.00   0.50    1.00    --   76.97-125.00-120.00   50
 26  \w     76.00 102.00   0.50    1.00    --   76.97-125.00  30.00   52
 27  \w     38.00  63.00   0.50    0.50    --   73.19-111.00  77.00   50
 28  \w     35.00  79.00   0.50    0.50    --   65.75-111.00  77.00   88
 29  \w     36.00 102.00   0.50    1.00    --   76.97-125.00 120.00  132
 30  \w   -111.00 -62.00   0.50    0.50    --  -73.25 147.00 125.61   98
 31  \w   -108.00 -79.00   0.50    0.50    --  -73.25 146.00  73.70   58
 32  \w    -64.00 -38.00   0.50    0.50    --  -67.30 125.00  60.00   52
 33  \w    -80.00 -55.00   0.50    0.50    --  -67.30 111.00 171.00   50
 34  \w    -92.00 -28.00   0.50    0.50    --  -67.30 125.00 -60.00  128
 35  \w    -92.00 -46.00   0.50    0.50    --  -67.30 125.00 -90.00   92
 36  \w    -92.00 -58.00   0.50    0.50    --  -67.30 125.00-120.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix-Arc 150'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0770561000
_diffrn_orient_matrix_UB_12      0.0944699000
_diffrn_orient_matrix_UB_13      0.0738742000
_diffrn_orient_matrix_UB_21      -0.0943365000
_diffrn_orient_matrix_UB_22      -0.1370443000
_diffrn_orient_matrix_UB_23      0.0118288000
_diffrn_orient_matrix_UB_31      0.1412205000
_diffrn_orient_matrix_UB_32      0.0345936000
_diffrn_orient_matrix_UB_33      0.1602057000
_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  0.0085
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12419
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.125
_diffrn_reflns_theta_min         4.880
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.685
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
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    1.215
_exptl_crystal_description       prism
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0030(5)
_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   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0433P)^2^+0.2384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3033
_reflns_number_total             3276
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00294a2.cif
_cod_data_source_block           jft-r478
_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_database_code               1566364
_shelx_shelxl_version_number     2018/3
_audit_contact_author            'Farzaneh Fadaei Tirani'
_chemical_oxdiff_formula         'C15 H21 F2 N3 O'
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.793
_reflns_odcompleteness_completeness 98.11
_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:
 C10(H10), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              35333
_shelx_hkl_checksum              91836
_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 1.275
_oxdiff_exptl_absorpt_empirical_full_min 0.839