One-Pot Synthesis of 2-Cyano-1,4-diketones: Applications to Synthesis of Cyanosubstituted Furans, Pyrroles, and Dihydropyridazines.
Chan, Chieh-Kai; Chan, Yi-Ling; Tsai, Yu-Lin; Chang, Meng-Yang; The Journal of organic chemistry 81 (2016) 8112–8120; doi:10.1021/acs.joc.6b01672

data_4037185
_publ_section_title
;
 One-Pot Synthesis of 2-Cyano-1,4-diketones: Applications to Synthesis of
 Cyanosubstituted Furans, Pyrroles, and Dihydropyridazines.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8112
_journal_page_last               8120
_journal_paper_doi               10.1021/acs.joc.6b01672
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C17 H11 F2 N3'
_chemical_formula_weight         295.29
_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
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 97.264(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.100(4)
_cell_length_b                   7.4176(12)
_cell_length_c                   6.8847(11)
_cell_measurement_reflns_used    2731
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.0780
_cell_measurement_theta_min      2.2732
_cell_volume                     1372.8(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.754
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.754
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            11369
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.754
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.466
_diffrn_reflns_theta_min         0.757
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_correction_T_min  0.8960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Lump
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.032
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.185
_refine_ls_extinction_coef       0.030(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1825
_refine_ls_R_factor_gt           0.1715
_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^)+(0.1645P)^2^+38.8349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4660
_refine_ls_wR_factor_ref         0.4718
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2451
_reflns_number_total             2843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01672_si_003.cif
_cod_data_source_block           150434LT
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037185
_shelxl_version_number           2014/6
_shelx_res_checksum              84354
_shelx_hkl_checksum              91937