Graphene oxide-catalyzed trifluoromethylation of alkynes with quinoxalinones and Langlois' reagent
Li, Hong; Peng, Xiangjun; Nie, Liang; Zhou, Lin; Yang, Ming; Li, Fan; Hu, Jian; Yao, Zhiyang; Liu, Liangxian; RSC Advances 11 (2021) 38667–38673; doi:10.1039/D1RA07014B

data_7243982
_publ_section_title
;
 Graphene oxide-catalyzed trifluoromethylation of alkynes with
 quinoxalinones and Langlois' reagent
;
_journal_issue                   61
_journal_name_full               'RSC Advances'
_journal_page_first              38667
_journal_page_last               38673
_journal_paper_doi               10.1039/D1RA07014B
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C19 H15 F3 N2 O'
_chemical_formula_sum            'C19 H15 F3 N2 O'
_chemical_formula_weight         344.33
_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     direct
_audit_creation_date             2020-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-07 deposited with the CCDC.	2021-11-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 118.7457(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2095(6)
_cell_length_b                   12.2629(6)
_cell_length_c                   12.3037(6)
_cell_measurement_reflns_used    6979
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.477
_cell_measurement_theta_min      3.263
_cell_volume                     1615.14(14)
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 QUEST'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71076
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23123
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.243
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_min         3.263
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0713
_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^)+(0.0410P)^2^+1.1607P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1474
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2475
_reflns_number_total             3703
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra07014b2.cif
_cod_data_source_block           20200923_lh_110_2_0m
_cod_original_cell_volume        1615.13(14)
_cod_database_code               7243982
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.972
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4AA(H4AA,H4AB)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C15(H15), C5AA(H5AA),
 C6AA(H6AA), C7AA(H7AA)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_olex2_submission_special_instructions 'No special instructions were received'