Single-carbon-atom transfer to <i>para</i>-quinone methides from TMSCF<sub>2</sub>Br.
Sun, Ruikang; Zhang, Pei; Yan, Yong; Zhu, Jie; Chen, Qirui; Yang, Chi; Lin, Aijun; Li, Xuanyi; Gao, Shang; Yao, Hequan; Chemical science 16 (2025) 12324–12331; doi:10.1039/d5sc03234b

data_1574802
_publ_section_title
;
 Single-carbon-atom transfer to <i>para</i>-quinone methides from
 TMSCF<sub>2</sub>Br.
;
_journal_issue                   27
_journal_name_full               'Chemical science'
_journal_page_first              12324
_journal_page_last               12331
_journal_paper_doi               10.1039/d5sc03234b
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C29 H40 O4'
_chemical_formula_sum            'C29 H40 O4'
_chemical_formula_weight         452.61
_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             2024-05-18
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-18 deposited with the CCDC.	2025-06-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.188(2)
_cell_angle_beta                 102.380(2)
_cell_angle_gamma                104.147(2)
_cell_formula_units_Z            4
_cell_length_a                   10.6394(6)
_cell_length_b                   10.7112(6)
_cell_length_c                   23.9695(13)
_cell_measurement_reflns_used    5302
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.352
_cell_measurement_theta_min      2.195
_cell_volume                     2582.7(3)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.1508
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_number            10326
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_min         1.964
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.8562
_exptl_absorpt_correction_T_min  0.5236
_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 0.0924 before and 0.0591 after correction.
 
For component 2:
 wR2(int) was 0.1476 before and 0.0673 after correction.
 The Ratio of minimum to maximum transmission is 0.74.

Final HKLF 4 output contains 34364 reflections, Rint = 0.0678
 (16816 with I > 3sig(I), Rint = 0.0559)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.070
_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     615
_refine_ls_number_reflns         10326
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.1420
_refine_ls_R_factor_gt           0.0866
_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^)+(0.1206P)^2^+1.8926P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2220
_refine_ls_wR_factor_ref         0.2458
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6371
_reflns_number_total             10326
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc03234b2.cif
_cod_data_source_block           mo_20240958_0m_4
_cod_depositor_comments          'Adding full bibliography for 1574802.cif.'
_cod_database_code               1574802
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.989
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C8(H8), C12(H12), C42(H42), C46(H46), C44(H44)
2.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C57(H57A,H57B)
2.c Aromatic/amide H refined with riding coordinates:
 C39(H39), C41(H41), C6(H6), C26(H26), C48(H48), C14(H14), C18(H18), C49(H49),
 C17(H17), C52(H52), C16(H16), C51(H51), C50(H50), C15(H15)
2.d Idealised Me refined as rotating group:
 C53(H53A,H53B,H53C), C61(H61A,H61B,H61C), C33(H33A,H33B,H33C), C19(H19A,H19B,
 H19C), C25(H25A,H25B,H25C), C1(H1A,H1B,H1C), C63(H63A,H63B,H63C), C32(H32A,
 H32B,H32C), C28(H28A,H28B,H28C), C62(H62A,H62B,H62C), C66(H66A,H66B,H66C),
 C30(H30A,H30B,H30C), C65(H65A,H65B,H65C), C29(H29A,H29B,H29C), C59(H59A,H59B,
 H59C), C34(H34A,H34B,H34C), C24(H24A,H24B,H24C), C58(H58A,H58B,H58C)
2.e Idealised tetrahedral OH refined as rotating group:
 O31(H31), O64(H64)
;
_olex2_submission_special_instructions 'No special instructions were received'