Direct C-H magnesiation of thiophenes with a Mg-Mg-bonded compound
Yang, Li; Sun, Zhenzhou; Wang, Lin; Geng, Jianqi; Wu, Biao; Yang, Xiao-Juan; Chemical Communications  (2026) –; doi:10.1039/D6CC00381H

data_7135620
_publ_section_title
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 Direct C-H magnesiation of thiophenes with an Mg-Mg-bonded compound.
;
_journal_issue                   27
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7172
_journal_page_last               7175
_journal_paper_doi               10.1039/d6cc00381h
_journal_volume                  62
_journal_year                    2026
_chemical_formula_moiety         'C40 H53 K Mg N2 O S'
_chemical_formula_sum            'C40 H53 K Mg N2 O S'
_chemical_formula_weight         673.31
_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
_audit_creation_date             2025-04-15
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2026-01-16 deposited with the CCDC.	2026-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.559(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   38.2556(19)
_cell_length_b                   10.5263(6)
_cell_length_c                   19.3654(11)
_cell_measurement_reflns_used    9963
_cell_measurement_temperature    180.00
_cell_measurement_theta_max      22.74
_cell_measurement_theta_min      2.25
_cell_volume                     7783.2(7)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      180.00
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0633
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            65196
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.436
_diffrn_reflns_theta_min         2.251
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6927
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0998 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.9295.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_description       block
_exptl_crystal_F_000             2896
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         7162
_refine_ls_number_restraints     190
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0897
_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^)+(0.0906P)^2^+30.2739P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2285
_refine_ls_wR_factor_ref         0.2519
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4880
_reflns_number_total             7162
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6cc00381h2.cif
_cod_data_source_block           1_a_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7135613--7135622.cif.'
_cod_database_code               7135620
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.970
_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. Restrained distances
 S1-C32 = S1-C29
 1.695 with sigma of 0.02
 S1-C29 = S1-C32
 1.695 with sigma of 0.02
 C30-C29
 1.37 with sigma of 0.02
 C31-C30
 1.42 with sigma of 0.02
 S1-C29 \\sim S1-C32
 with sigma of 0.02
 S1-C32 \\sim S1A-C32A
 with sigma of 0.02
 C33-C34 \\sim C33A-C34A
 with sigma of 0.02
 C33-C32 \\sim C33A-C32A
 with sigma of 0.02
 C34-C35 \\sim C34A-C35A
 with sigma of 0.02
 C35-C36 \\sim C35A-C36A
 with sigma of 0.02
 C36-C31 \\sim C36A-C31A
 with sigma of 0.02
 C31-C32 \\sim C31A-C32A
 with sigma of 0.02
 Mg1-S1 \\sim Mg1-S1A
 with sigma of 0.04
 S1-C33 \\sim S1A-C33A
 with sigma of 0.04
 S1-C31 \\sim S1A-C31A
 with sigma of 0.04
 C33-C35 \\sim C33A-C35A
 with sigma of 0.04
 C33-C31 \\sim C33A-C31A
 with sigma of 0.04
 C34-C36 \\sim C34A-C36A
 with sigma of 0.04
 C34-C32 \\sim C34A-C32A
 with sigma of 0.04
 C35-C31 \\sim C35A-C31A
 with sigma of 0.04
 C36-C32 \\sim C36A-C32A
 with sigma of 0.04
3. Rigid bond restraints
 C32A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
S1 \\sim C29 \\sim C30 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim
C36: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 S1, C29, C30, C31, C32, C33, C34, C35, C36
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S1A, C31A, C32A, C33A, C34A, C35A, C36A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(S1A)=Sof(C33A)=Sof(H33A)=Sof(C34A)=Sof(H34A)=Sof(C35A)=Sof(H35A)=
 Sof(C36A)=Sof(H36A)=Sof(C31A)=Sof(C32A)=1-FVAR(1)
 Sof(S1)=Sof(C33)=Sof(H33)=Sof(C34)=Sof(H34)=Sof(C35)=Sof(H35)=Sof(C36)=
 Sof(H36)=Sof(C31)=Sof(C32)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C23(H23), C26(H26)
7.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B)
7.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C19(H19), C20(H20), C21(H21), C30(H30), C33(H33),
 C34(H34), C35(H35), C36(H36), C33A(H33A), C34A(H34A), C35A(H35A), C36A(H36A)
7.d Fitted hexagon refined as free rotating group:
 C33(C34,C35,C36,C31,C32), C33A(C34A,C35A,C36A,C31A,C32A)
7.e Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'