NIS-mediated regioselective addition of allenamides with pyrazoles: synthesis of iodo-substituted allylic pyrazoles
Cheng, Song; Gu, Wen; Zhao, Kun; Zhang, Shu Ting; Yang, Lan; Liu, Qing Song; Li, Xiao Xiao; Zhao, Zhi Gang; New Journal of Chemistry 47 (2023) 19698–19708; doi:10.1039/D3NJ03326K

data_7062858
_publ_section_title
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 NIS-mediated regioselective addition of allenamides with pyrazoles:
 synthesis of iodo-substituted allylic pyrazoles
;
_journal_issue                   42
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19698
_journal_page_last               19708
_journal_paper_doi               10.1039/D3NJ03326K
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C25 H22 I N3 O2 S'
_chemical_formula_sum            'C25 H22 I N3 O2 S'
_chemical_formula_weight         555.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-04 deposited with the CCDC.	2023-09-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.101(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2348(6)
_cell_length_b                   23.802(2)
_cell_length_c                   10.5882(9)
_cell_measurement_reflns_used    4107
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.97
_cell_measurement_theta_min      2.59
_cell_volume                     2298.1(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_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  0.0606
_diffrn_reflns_av_unetI/netI     0.0671
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15553
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.506
_diffrn_reflns_theta_min         2.128
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.512
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6606
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0919 before and 0.0549 after correction.
The Ratio of minimum to maximum transmission is 0.8860.
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    1.605
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.323
_refine_diff_density_min         -0.924
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         5225
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0414P)^2^+4.2486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3548
_reflns_number_total             5225
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03326k2.cif
_cod_data_source_block           mo_lxx_230328_150k_0m_a
_cod_database_code               7062858
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.704
_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. Rigid bond restraints
 C008, C00V
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C008, C00N
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
C008 \\sim C00V: within 2A with sigma of 0.01 and sigma for terminal atoms of
0.02 within 2A
C008 \\sim C00N: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02 within 2A
Uanis(C008) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C00D(H00D)
4.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00C(H00C), C00F(H00F), C00H(H00H), C00J(H00J), C00K(H00K),
 C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V)
4.c X=CH2 refined with riding coordinates:
 C00M(H00A,H00B)
4.d Idealised Me refined as rotating group:
 C00W(H00E,H00G,H00I)
;
_shelx_res_checksum              84496
_olex2_submission_special_instructions 'No special instructions were received'