Synthesis of di/trifluoromethyl cyclopropane-dicarbonitriles via [2 + 1] annulation of fluoro-based diazoethanes with (alkylidene)malononitriles
Gao, Cheng-Feng; Chen, Yue-Ji; Nie, Jing; Zhang, Fa-Guang; Cheung, Chi Wai; Ma, Jun-An; Chemical Communications  (2023) –; doi:10.1039/D3CC03897A

data_7132079
_publ_section_title
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 Synthesis of di/trifluoromethyl cyclopropane-dicarbonitriles via [2 + 1]
 annulation of fluoro-based diazoethanes with (alkylidene)malononitriles
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_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03897A
_journal_year                    2023
_chemical_formula_moiety         'C18 H14 F2 N2 O3 S'
_chemical_formula_sum            'C18 H14 F2 N2 O3 S'
_chemical_formula_weight         376.37
_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     dual
_audit_creation_date             2021-10-10
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_audit_update_record
;
2022-04-05 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.105(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.160(2)
_cell_length_b                   5.2325(5)
_cell_length_c                   20.233(2)
_cell_measurement_reflns_used    4075
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.75
_cell_measurement_theta_min      2.19
_cell_volume                     1671.0(3)
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1047
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            34639
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.621
_diffrn_reflns_theta_min         2.059
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1342 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.9347.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         4685
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.2442P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2872
_reflns_number_total             4685
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03897a2.cif
_cod_data_source_block           cyj913
_cod_database_code               7132079
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.924
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009), C00E(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q)
2.c X=CH2 refined with riding coordinates:
 N008(H00A,H00B)
;
_shelx_res_checksum              44147
_shelx_hkl_checksum              58888
_olex2_submission_special_instructions 'No special instructions were received'