Copper-catalysed decarboxylative alkynylation-cyclization reaction of propargylic cyclic carbonates with nitrile imines to access tetrasubstituted pyrazoles.
Yu, Xiaowen; Li, Jinxia; Duan, Jiongjiong; Fan, Feifei; Xie, Huanping; Huang, Yanfan; Shi, Shukui; Kong, Weiguang; Li, Ting; Chemical communications (Cambridge, England) 62 (2026) 6600–6603; doi:10.1039/d5cc06713h

data_7135570
_publ_section_title
;
 Copper-catalysed decarboxylative alkynylation-cyclization reaction of
 propargylic cyclic carbonates with nitrile imines to access
 tetrasubstituted pyrazoles.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6600
_journal_page_last               6603
_journal_paper_doi               10.1039/d5cc06713h
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C29 H21 Cl N2 O3'
_chemical_formula_sum            'C29 H21 Cl N2 O3'
_chemical_formula_weight         480.93
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-07-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2025-07-26 deposited with the CCDC.	2026-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.3289(9)
_cell_length_b                   17.9535(8)
_cell_length_c                   7.4598(3)
_cell_measurement_reflns_used    7515
_cell_measurement_temperature    299(2)
_cell_measurement_theta_max      22.401
_cell_measurement_theta_min      2.223
_cell_volume                     2454.78(19)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      299.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0799
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            36300
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.320
_diffrn_reflns_theta_min         2.222
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6771
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1445 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.9080.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1455 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5812
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0490
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0563P)^2^+0.8334P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1400
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_full    0.927
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                4242
_reflns_number_total             5812
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06713h2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7135569--7135570.cif.'
_cod_database_code               7135570
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.958
_olex2_refinement_description
;
1. 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
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C4(H4), C16(H16), C12(H12), C25(H25), C3(H3), C14(H14),
 C27(H27), C13(H13), C29(H29), C26(H26), C15(H15), C28(H28)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              56618
_shelx_hkl_checksum              49903
_olex2_submission_special_instructions 'No special instructions were received'