Metal-free four-component coupling of cyclic diarylchloronium salts, tetrahydrothiophene, amines and carbon dioxide.
Kang, Bangxiong; Li, Wei; Jiang, Huanfeng; Qi, Chaorong; Chemical communications (Cambridge, England) 61 (2025) 3395–3398; doi:10.1039/d4cc05919k

data_7134196
_publ_section_title
;
 Metal-free four-component coupling of cyclic diarylchloronium salts,
 tetrahydrothiophene, amines and carbon dioxide.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3395
_journal_page_last               3398
_journal_paper_doi               10.1039/d4cc05919k
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C23 H30 Cl N O2 S'
_chemical_formula_sum            'C23 H30 Cl N O2 S'
_chemical_formula_weight         419.99
_chemical_name_systematic
'4-((2'-chloro-4,4'-dimethyl-[1,1'-biphenyl]-3-yl)thio)butyl butylcarbamate'
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-01
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_audit_update_record
;
2024-08-03 deposited with the CCDC.	2025-01-24 downloaded from the CCDC.
;
_cell_angle_alpha                98.541(2)
_cell_angle_beta                 98.294(2)
_cell_angle_gamma                90.455(2)
_cell_formula_units_Z            12
_cell_length_a                   14.5277(6)
_cell_length_b                   14.8392(6)
_cell_length_c                   32.2982(14)
_cell_measurement_reflns_used    5256
_cell_measurement_temperature    100
_cell_measurement_theta_max      63.822
_cell_measurement_theta_min      2.797
_cell_volume                     6810.5(5)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.1196
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            21724
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        63.984
_diffrn_reflns_theta_max         63.983
_diffrn_reflns_theta_min         2.797
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.481
_exptl_absorpt_correction_T_max  0.7856
_exptl_absorpt_correction_T_min  0.5623
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1469 before and 0.0814 after correction.
 
For component 2:
 wR2(int) was 0.1511 before and 0.0814 after correction.
 The Ratio of minimum to maximum transmission is 0.61.

Final HKLF 4 output contains 79988 reflections, Rint = 0.1421
 (36823 with I > 3sig(I), Rint = 0.1122)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       needle
_exptl_crystal_F_000             2688
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Dichloromethane/n-Hexane'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.564
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1532
_refine_ls_number_reflns         21724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.1397
_refine_ls_R_factor_gt           0.1021
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1217P)^2^+21.3606P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2603
_refine_ls_wR_factor_ref         0.2948
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15417
_reflns_number_total             21724
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc05919k2.cif
_cod_data_source_block           kb_0m_4
_cod_depositor_comments          'Adding full bibliography for 7134196.cif.'
_cod_database_code               7134196
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.952
_shelx_estimated_absorpt_t_min   0.692
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.6032(14)
 0.3968(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Secondary CH2 refined with riding coordinates:
 C014(H01A,H01B), C017(H01O,H01P), C018(H01Q,H01R), C18(H18A,H18B), C01B(H01C,
 H01D), C01D(H01E,H01F), C01F(H01G,H01H), C01G(H01S,H01T), C01I(H01V,H01W),
 C01J(H01Z,H), C01K(H01I,H01J), C01L(H01,HA), C16(H16A,H16B), C01N(H01K,H01L),
 C01O(H01M,H01N), C17(H17A,H17B), C15(H15A,H15B), C01W(H01X,H01Y), C01Y(H2,HB),
 C01Z(H5,HC), C028(H02Q,H02R), C02O(H02L,H02O), C02R(H02E,H02F), C02U(H02A,
 H02B), C02Y(H02C,H02D), C030(H03A,H03B), C032(H03P,H03Q), C20(H20A,H20B),
 C036(H03C,H03D), C03A(H03X,H03Y), C03D(H03M,H03N), C03L(H03K,H03L), C21(H21A,
 H21B), C03N(H14,HD), C03U(H16,HE), C03W(H17,HF), C22(H22A,H22B), C043(H04A,
 H04B), C046(H6,HI), C047(H04K,H04L), C04B(H18,HL), C04I(H04V,H04W)
3.b Aromatic/amide H refined with riding coordinates:
 N00P(H00P), N1(H1), N3(H3A), N00T(H00T), N00U(H00U), C00X(H00X), N2(H2A),
 C010(H010), C012(H012), C7(H7), C01U(H01U), C11(H11), C022(H022), C10(H10),
 C4(H4), C02B(H02J), C02G(H02S), C02I(H02K), C9(H9), C02M(H02M), C02N(H02N),
 C02P(H02P), C3(H3), C02X(H02X), C02Z(H02Z), C034(H034), C038(H038), C03B(H03),
 C03E(H03H), C03H(H13), C03I(H03I), C03J(H03J), C03O(H03O), C03P(H15),
 C03S(H03S), C03T(H03T), C03V(H03V), C03Z(H03Z), C044(H044), C048(H048),
 C04C(H04C), C04D(H04D)
3.c Idealised Me refined as rotating group:
 C02T(H02G,H02H,H02I), C14(H14A,H14B,H14C), C039(H03R,H03U,H03W), C1(H1A,H1B,
 H1C), C03Y(H03E,H03F,H03G), C042(H04,HG,HH), C049(H04M,H04N,H04O), C04A(H8,HJ,
 HK), C04E(H04S,H04T,H04U), C04F(H04P,H04Q,H04R), C04G(H04E,H04F,H04G),
 C04H(H19,HM,HN), C04J(H04H,H04I,H04J), C04K(H04X,H04Y,HO), C04L(H12,HP,HQ),
 C04M(H20,HR,HS), C23(H23A,H23B,H23C), C04O(H04Z,HT,HU)
;
_olex2_submission_special_instructions 'No special instructions were received'