Visible-light-induced mesoporous graphitic carbon nitride-catalyzed trifluoromethylation and perfluoroalkylation of 4-aminocoumarins
Li, Ning-Bo; Gu, Shuo; Hu, Chu-Qian; Wang, Yu-Xin; Zhou, Xue; Qiao, Jie; Jiang, Jun; Ji, Hong-Tao; He, Wei-Min; New Journal of Chemistry 47 (2023) 660–665; doi:10.1039/D2NJ05304G

data_7062139
_publ_section_title
;
 Visible-light-induced mesoporous graphitic carbon nitride-catalyzed
 trifluoromethylation and perfluoroalkylation of 4-aminocoumarins
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              660
_journal_page_last               665
_journal_paper_doi               10.1039/D2NJ05304G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C12 H6 F7 N O2'
_chemical_formula_sum            'C12 H6 F7 N O2'
_chemical_formula_weight         329.18
_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     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2c18xm
_audit_creation_date             2022-01-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-31 deposited with the CCDC.	2022-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                80.950(5)
_cell_angle_beta                 85.782(5)
_cell_angle_gamma                80.900(5)
_cell_formula_units_Z            2
_cell_length_a                   7.2140(12)
_cell_length_b                   7.4875(12)
_cell_length_c                   11.7137(18)
_cell_measurement_reflns_used    4715
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.90
_cell_measurement_theta_min      3.07
_cell_volume                     616.20(17)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12962
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.571
_diffrn_reflns_theta_min         3.069
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0849 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.8767.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2850
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0604
_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^)+(0.1006P)^2^+0.2153P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1639
_refine_ls_wR_factor_ref         0.1913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1767
_reflns_number_total             2850
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj05304g2.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 7062139.cif.'
_cod_database_code               7062139
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Rigid bond restraints
 F2, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C11(H11)
3.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_shelx_res_checksum              69892
_olex2_submission_special_instructions 'No special instructions were received'