Water-promoted defluorinative synthesis of fluoroalkylated 1,5-diazapentadienes by using (NH4)2CO3 as an NH2 and NH source
Han, Wei; Chen, Yu-Lan; Tang, Xi; Zhou, Jie; Ma, Mengtao; Shen, Zhi-Liang; Chu, Xue-Qiang; Green Chemistry 25 (2023) 9672–9679; doi:10.1039/D3GC03717G

data_7247704
_publ_section_title
;
 Water-promoted defluorinative synthesis of fluoroalkylated
 1,5-diazapentadienes by using (NH4)2CO3 as an NH2 and NH source
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              9672
_journal_page_last               9679
_journal_paper_doi               10.1039/D3GC03717G
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C19 H14 F7 N O3 S'
_chemical_formula_sum            'C19 H14 F7 N O3 S'
_chemical_formula_weight         469.37
_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     direct
_audit_creation_date             2023-07-07
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-07-07 deposited with the CCDC.	2023-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                81.051(7)
_cell_angle_beta                 85.123(9)
_cell_angle_gamma                84.276(11)
_cell_formula_units_Z            2
_cell_length_a                   6.2755(10)
_cell_length_b                   8.1410(9)
_cell_length_c                   19.0094(12)
_cell_measurement_reflns_used    3018
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.2190
_cell_measurement_theta_min      4.6970
_cell_volume                     952.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -63.00  30.00   1.00    1.00    --  -40.73  38.00  30.00   93
  2  \w    -72.00  23.00   1.00    1.00    --  -40.73  77.00 120.00   95
  3  \w     33.00  76.00   1.00    1.00    --   40.73-125.00 -90.00   43
  4  \w     59.00  85.00   1.00    1.00    --   40.73-125.00   0.00   26
  5  \w     52.00 120.00   1.00    1.00    --  106.95 -45.00 120.00   68
  6  \w     83.00 178.00   1.00    1.00    --  106.95  30.00  60.00   95
  7  \w    151.00 177.00   1.00    1.00    --  106.95 125.00 -30.00   26
  8  \w    114.00 155.00   1.00    1.00    --  106.95 125.00 -90.00   41
  9  \w     99.00 130.00   1.00    1.00    --  106.95 125.00 -30.00   31
 10  \w     95.00 165.00   1.00    1.00    --  106.95 125.00  60.00   70
 11  \w    100.00 172.00   1.00    1.00    --  106.95  30.00 -30.00   72
 12  \w     82.00 133.00   1.00    1.00    --  106.95 -45.00-120.00   51
 13  \w     79.00 109.00   1.00    1.00    --  106.95 -95.00 -60.00   30
 14  \w     44.00 108.00   1.00    1.00    --  106.95 -95.00  30.00   64
 15  \w     60.00 103.00   1.00    1.00    --  106.95 -95.00 120.00   43
 16  \w     47.00 130.00   1.00    1.00    --  106.95 -45.00   0.00   83
 17  \w     41.00 121.00   1.00    1.00    --  106.95-125.00 -60.00   80
 18  \w   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00-150.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1955539000
_diffrn_orient_matrix_UB_12      -0.0722113000
_diffrn_orient_matrix_UB_13      0.0442336000
_diffrn_orient_matrix_UB_21      -0.1098218000
_diffrn_orient_matrix_UB_22      0.1778479000
_diffrn_orient_matrix_UB_23      0.0001700000
_diffrn_orient_matrix_UB_31      -0.1042735000
_diffrn_orient_matrix_UB_32      -0.0117916000
_diffrn_orient_matrix_UB_33      -0.0693388000
_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  0.0882
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5808
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         2.359
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.365
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.906
_refine_diff_density_min         -1.187
_refine_diff_density_rms         0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3370
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0955
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2680
_refine_ls_wR_factor_ref         0.2865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2707
_reflns_number_total             3370
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3gc03717g2.cif
_cod_data_source_block           3004
_cod_depositor_comments
'Adding full bibliography for 7247703--7247704.cif.'
_cod_database_code               7247704
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C14(H14), C15(H15),
 C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              85108
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.707
_oxdiff_exptl_absorpt_empirical_full_min 0.312