Polyfluoroalkylated antipyrines in Pd-catalyzed transformations
Shchegolkov, Evgeny V.; Burgart, Yanina V.; Matsneva, Daria A.; Borisevich, Sophia S.; Kadyrova, Renata A.; Orshanskaya, Iana R.; Zarubaev, Vladimir V.; Saloutin, Victor I.; RSC Advances 11 (2021) 35174–35181; doi:10.1039/D1RA06967E

data_7243810
_publ_section_title
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 Polyfluoroalkylated antipyrines in Pd-catalyzed transformations
;
_journal_issue                   56
_journal_name_full               'RSC Advances'
_journal_page_first              35174
_journal_page_last               35181
_journal_paper_doi               10.1039/D1RA06967E
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C18 H12 F6 N2 O'
_chemical_formula_sum            'C18 H12 F6 N2 O'
_chemical_formula_weight         386.30
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-17 deposited with the CCDC.	2021-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                93.734(6)
_cell_angle_beta                 90.935(6)
_cell_angle_gamma                95.221(6)
_cell_formula_units_Z            4
_cell_length_a                   8.6416(7)
_cell_length_b                   11.0188(9)
_cell_length_c                   18.0722(14)
_cell_measurement_reflns_used    2223
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      22.5630
_cell_measurement_theta_min      3.7390
_cell_volume                     1709.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)'
_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, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.5253
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.987
_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    -39.00   5.00   1.00   50.00    --   22.52 -87.00  20.00   44
  2  \w    -11.00  14.00   1.00   50.00    --   22.52  87.00 137.00   25
  3  \w    -60.00  39.00   1.00   50.00    --  -23.92  87.00 137.00   99
  4  \w    -26.00   0.00   1.00   50.00    --  -23.92 -87.00  20.00   26
  5  \w     35.00  98.00   1.00   50.00    --   22.52 178.00 150.00   63
  6  \w    -25.00  64.00   1.00   50.00    --   22.52 -99.00 -30.00   89
  7  \w     -3.00  95.00   1.00   50.00    --   22.52  38.00 -60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0896
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15737
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.276
_diffrn_reflns_theta_min         3.612
_exptl_absorpt_coefficient_mu    0.139
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63424
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       prism
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     584
_refine_ls_number_reflns         8397
_refine_ls_number_restraints     66
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0569
_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^)+(0.0565P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1816
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3326
_reflns_number_total             8397
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra06967e2.cif
_cod_data_source_block           exp_1081
_cod_database_code               7243810
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.948
_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. Restrained distances
 C11B-C10B
 1.4 with sigma of 0.02
 C9-C8B
 1.4 with sigma of 0.02
 C8B-C7B
 1.4 with sigma of 0.02
 C10B-C9
 1.4 with sigma of 0.02
 C7B-C6
 1.4 with sigma of 0.02
 C11B-C6
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F4A) \\sim Ueq, Uanis(F6B) \\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F5B)
\\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F4B) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C10B) \\sim Ueq, Uanis(C11B) \\sim Ueq, Uanis(C8B) \\sim Ueq, Uanis(C7B)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: C7(0.93) H7(0.93) C8(0.93) H8(0.93) C10(0.93) H10(0.93) C11(0.93)
 H11(0.93) F4A(0.4) F5A(0.4) F6A(0.4) F4B(0.6) F5B(0.6) F6B(0.6) C8B(0.07)
 H8B(0.07) C7B(0.07) H7B(0.07) C11B(0.07) H11B(0.07) C10B(0.07) H10B(0.07)
5.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C17A(H17A), C8B(H8B), C7B(H7B), C11B(H11B), C10B(H10B)
5.b Idealised Me refined as rotating group:
 C01E(H01A,H01B,H01C), C019(H01D,H01E,H01F)
;
_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
;