A Protocol for the Synthesis of CF<sub>2</sub>H-Containing Pyrazolo[1,5- c]quinazolines from 3-Ylideneoxindoles and in Situ Generated CF<sub>2</sub>HCHN<sub>2</sub>.
Han, Wen-Yong; Wang, Jian-Shu; Zhao, Jia; Long, Lin; Cui, Bao-Dong; Wan, Nan-Wei; Chen, Yong-Zheng; The Journal of organic chemistry 83 (2018) 6556–6565; doi:10.1021/acs.joc.8b00866

data_4035834
_publ_section_title
;
 A Protocol for the Synthesis of CF<sub>2</sub>H-Containing Pyrazolo[1,5-
 c]quinazolines from 3-Ylideneoxindoles and in Situ Generated
 CF<sub>2</sub>HCHN<sub>2</sub>.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6556
_journal_page_last               6565
_journal_paper_doi               10.1021/acs.joc.8b00866
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C15 H13 F2 N3 O3'
_chemical_formula_sum            'C15 H13 F2 N3 O3'
_chemical_formula_weight         321.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 108.024(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2544(15)
_cell_length_b                   17.5322(14)
_cell_length_c                   7.5684(10)
_cell_measurement_reflns_used    902
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.5240
_cell_measurement_theta_min      4.0430
_cell_volume                     1420.1(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku RIPIDII'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9459
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         3.973
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0649P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1563
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1537
_reflns_number_total             2893
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00866_si_001.cif
_cod_data_source_block           zj-2-dj
_cod_database_code               4035834
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.953
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0(10)
 1(10)
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 Ternary CH refined with riding coordinates:
 C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C2(H2)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              20643
_shelx_hkl_checksum              6870
_olex2_submission_special_instructions 'No special instructions were received'