In situ generated CF3CHN2 with 3-ylideneoxindoles to access CF3-containing pyrazolo[1,5-c]quinazolines derivatives
Hu, Ming-Cheng; Zhou, Hai-Tao; Fang, Yu-Chen; Zhang, Li-Ren; Cui, Bao-Dong; Chen, Yong-Zheng; Bai, Mei; RSC Advances 14 (2024) 36410–36415; doi:10.1039/D4RA06651K

data_7249594
_publ_section_title
;
 In situ generated CF3CHN2 with 3-ylideneoxindoles to access
 CF3-containing pyrazolo[1,5-c]quinazolines derivatives
;
_journal_issue                   49
_journal_name_full               'RSC Advances'
_journal_page_first              36410
_journal_page_last               36415
_journal_paper_doi               10.1039/D4RA06651K
_journal_volume                  14
_journal_year                    2024
_chemical_formula_moiety         'C15 H12 F3 N3 O3'
_chemical_formula_sum            'C15 H12 F3 N3 O3'
_chemical_formula_weight         339.28
_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             2023-07-28
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2024-04-21 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.535(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.8074(13)
_cell_length_b                   4.65278(14)
_cell_length_c                   26.1585(13)
_cell_measurement_reflns_used    7252
_cell_measurement_temperature    99.97(15)
_cell_measurement_theta_max      73.9710
_cell_measurement_theta_min      3.7910
_cell_volume                     2810.1(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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      99.97(15)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.964
_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    -32.00  -6.00   0.50    0.50    --    0.00 -82.00-120.00   52
  2  \w    -23.00   5.00   0.50    0.50    --    0.00 -82.00-180.00   56
  3  \w    -88.00  21.00   0.50    0.50    --    0.00 -57.00  90.00  218
  4  \w    -13.00  12.00   0.50    0.50    --    0.00 -82.00 150.00   50
  5  \w    -23.00   8.00   0.50    0.50    --    0.00 -82.00-150.00   62
  6  \w     49.00  99.00   0.50    0.80    --   95.80 -45.00-150.00  100
  7  \w      8.00  34.00   0.50    0.80    --   95.80 -45.00-150.00   52
  8  \w     84.00 121.00   0.50    0.80    --   95.80  30.00 -30.00   74
  9  \w     19.00 125.00   0.50    0.80    --   95.80 -77.00  30.00  212
 10  \w     84.00 147.00   0.50    0.80    --   95.80  30.00   0.00  126
 11  \w     78.00 176.00   0.50    0.80    --   95.80  15.00-120.00  196
 12  \w      6.00 110.00   0.50    0.80    --   95.80 -61.00  30.00  208
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0383205000
_diffrn_orient_matrix_UB_12      -0.0741146000
_diffrn_orient_matrix_UB_13      -0.0632679000
_diffrn_orient_matrix_UB_21      0.0542809000
_diffrn_orient_matrix_UB_22      -0.0865292000
_diffrn_orient_matrix_UB_23      -0.0066725000
_diffrn_orient_matrix_UB_31      -0.0059473000
_diffrn_orient_matrix_UB_32      -0.3108719000
_diffrn_orient_matrix_UB_33      0.0169483000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            5524
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.296
_diffrn_reflns_theta_min         3.234
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.219
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         5524
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.1181
_refine_ls_R_factor_gt           0.1144
_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^)+(0.1017P)^2^+29.6990P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3068
_refine_ls_wR_factor_ref         0.3085
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5101
_reflns_number_total             5524
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ra06651k2.cif
_cod_data_source_block           1b_2
_cod_database_code               7249594
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S F'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.735(7)
 0.265(7)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C29(H29A,H29B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C30(H30A,H30B,
 H30C)
;
_shelx_res_checksum              47728
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.942
_oxdiff_exptl_absorpt_empirical_full_min 0.560