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_7132080
_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 H16 F2 N2 O2 S'
_chemical_formula_sum            'C18 H16 F2 N2 O2 S'
_chemical_formula_weight         362.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-07-31
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
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_audit_update_record
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2023-07-31 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                76.0700(10)
_cell_angle_beta                 88.9940(10)
_cell_angle_gamma                82.2600(10)
_cell_formula_units_Z            4
_cell_length_a                   11.4509(2)
_cell_length_b                   11.4766(3)
_cell_length_c                   14.0514(3)
_cell_measurement_reflns_used    7303
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      74.74
_cell_measurement_theta_min      3.24
_cell_volume                     1775.75(7)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23977
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.921
_diffrn_reflns_theta_min         3.241
_diffrn_source_current           0.95
_diffrn_source_power             0.0475
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.926
_exptl_absorpt_correction_T_max  0.0872
_exptl_absorpt_correction_T_min  0.0097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1176 before and 0.0570 after correction.
The Ratio of minimum to maximum transmission is 0.1112.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.823
_refine_diff_density_min         -0.571
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         7255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0762
_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^)+(0.1565P)^2^+0.0133P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1938
_refine_ls_wR_factor_ref         0.2037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6257
_reflns_number_total             7255
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03897a2.cif
_cod_data_source_block           cu_0710_14_0m
_cod_database_code               7132080
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.831
_shelx_estimated_absorpt_t_min   0.699
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N00B(H00D), N00C(H00C)
2.b Ternary CH refined with riding coordinates:
 C00H(H00H), C00J(H00J), C00N(H00N), C00P(H00P)
2.c Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B), C00W(H00E,H00F)
2.d Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00M(H00M), C00S(H00S), C00T(H00T), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014),
 C015(H015), C016(H016), C017(H017), C018(H018), C019(H019), C01A(H01A),
 C01B(H01B), C01C(H01C), C01D(H01D), C01E(H01E)
;
_shelx_res_checksum              29586
_shelx_hkl_checksum              71552
_olex2_submission_special_instructions 'No special instructions were received'