Copper-mediated tandem ring-opening/cyclization reactions of cyclopropanols with aryldiazonium salts: synthesis of N-arylpyrazoles.
Liu, Jidan; Xu, Erjie; Jiang, Jinyuan; Huang, Zeng; Zheng, Liyao; Liu, Zhao-Qing; Chemical communications (Cambridge, England) 56 (2020) 2202–2205; doi:10.1039/c9cc09657d

data_7125822
_publ_section_title
;
 Copper-mediated tandem ring-opening/cyclization reactions of
 cyclopropanols with aryldiazonium salts: synthesis of N-arylpyrazoles.
;
_journal_issue                   14
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2202
_journal_page_last               2205
_journal_paper_doi               10.1039/c9cc09657d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C16 H13 Cl N2'
_chemical_formula_sum            'C16 H13 Cl N2'
_chemical_formula_weight         268.73
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-10-12 deposited with the CCDC.	2020-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 123.697(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.4385(9)
_cell_length_b                   9.3554(3)
_cell_length_c                   17.4150(8)
_cell_measurement_reflns_used    6241
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.398
_cell_measurement_theta_min      2.515
_cell_volume                     2634.9(2)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 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      170.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_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  0.0485
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14816
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         2.515
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1567 before and 0.0532 after correction. The Ratio of minimum to maximum transmission is 0.9076. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2684
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0367
_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^)+(0.0478P)^2^+2.9361P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1005
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2275
_reflns_number_total             2684
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09657d2.cif
_cod_data_source_block           zz
_cod_depositor_comments          'Adding full bibliography for 7125822.cif.'
_cod_database_code               7125822
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C2(H2), C16(H16), C12(H12), C4(H4), C8(H8), C15(H15),
 C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_olex2_submission_special_instructions 'No special instructions were received'