NIS-promoted three-component reaction of 3-oxo-3-arylpropanenitriles with arylsulfonyl hydrazides.
Wei, Yueting; Liu, Ping; Liu, Yali; He, Jing; Li, Xuezhen; Li, Shiwu; Zhao, Jixing; Organic & biomolecular chemistry 19 (2021) 3932–3939; doi:10.1039/d1ob00438g

data_7157994
_publ_section_title
;
 NIS-promoted three-component reaction of 3-oxo-3-arylpropanenitriles with
 arylsulfonyl hydrazides.
;
_journal_issue                   17
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3932
_journal_page_last               3939
_journal_paper_doi               10.1039/d1ob00438g
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C H Cl3, 3(C16 H12 F3 N3 S)'
_chemical_formula_sum            'C49 H37 Cl3 F9 N9 S3'
_chemical_formula_weight         1125.40
_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             2020-08-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-05 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;
_cell_angle_alpha                106.397(2)
_cell_angle_beta                 108.593(2)
_cell_angle_gamma                108.531(2)
_cell_formula_units_Z            2
_cell_length_a                   13.8799(8)
_cell_length_b                   14.9130(8)
_cell_length_c                   14.9991(7)
_cell_measurement_reflns_used    9830
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.72
_cell_measurement_theta_min      2.68
_cell_volume                     2523.1(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      173.0
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            32090
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.766
_diffrn_reflns_theta_min         2.294
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.385
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       block
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.931
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     719
_refine_ls_number_reflns         10688
_refine_ls_number_restraints     219
_refine_ls_restrained_S_all      1.169
_refine_ls_R_factor_all          0.0850
_refine_ls_R_factor_gt           0.0712
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0571P)^2^+6.9390P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1744
_refine_ls_wR_factor_ref         0.1828
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8785
_reflns_number_total             10688
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00438g1.cif
_cod_data_source_block           11_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7157992--7157994.cif.'
_cod_database_code               7157994
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.930
_shelx_estimated_absorpt_t_min   0.920
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C49A-Cl3A \\sim C49-Cl3
 with sigma of 0.02
 Cl1A-C49A \\sim Cl1-C49
 with sigma of 0.02
 Cl1A-Cl3A \\sim Cl1-Cl3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Cl1 \\sim Cl1A \\sim Cl2 \\sim Cl2A \\sim Cl3 \\sim Cl3A \\sim C49 \\sim C49A:
within 3.8A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F2) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F8) \\sim Ueq: with sigma of
0.002 and sigma for terminal atoms of 0.004
4. Rigid body (RIGU) restrains
 Cl1, Cl2, Cl3, C49
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl1A, Cl2A, Cl3A, C49A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Cl1A)=Sof(Cl2A)=Sof(Cl3A)=Sof(C49A)=Sof(H49A)=1-FVAR(1)
 Sof(Cl1)=Sof(Cl2)=Sof(Cl3)=Sof(C49)=Sof(H49)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C49(H49), C49A(H49A)
6.b Aromatic/amide H refined with riding coordinates:
 N5(H5), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28),
 C30(H30), C31(H31), N8(H8), C37(H37), C38(H38), C39(H39), C40(H40), C41(H41),
 C43(H43), C44(H44), C46(H46), C47(H47), N2(H2), C5(H5A), C6(H6), C7(H7),
 C8(H8A), C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
;
_shelx_res_checksum              77646
_olex2_submission_special_instructions 'No special instructions were received'