Access to distal <i>meta</i>-C-H functionalization of arylmethanesulfonic acid derivatives.
Srinivas, Dasari; Mounika, Kurella; Satyanarayana, Gedu; Chemical communications (Cambridge, England)  (2023) –; doi:10.1039/d3cc02260a

data_7131841
_publ_section_title
;
 Access to distal <i>meta</i>-C-H functionalization of arylmethanesulfonic
 acid derivatives.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc02260a
_journal_year                    2023
_chemical_formula_moiety         'C22 H29 Cl2 N O5 S'
_chemical_formula_sum            'C22 H29 Cl2 N O5 S'
_chemical_formula_weight         490.42
_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             2023-03-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-04-13 deposited with the CCDC.	2023-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                83.955(3)
_cell_angle_beta                 85.127(3)
_cell_angle_gamma                77.934(3)
_cell_formula_units_Z            2
_cell_length_a                   6.3605(5)
_cell_length_b                   11.1325(10)
_cell_length_c                   18.2872(15)
_cell_measurement_reflns_used    4195
_cell_measurement_temperature    299
_cell_measurement_theta_max      21.55
_cell_measurement_theta_min      2.24
_cell_volume                     1256.60(18)
_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)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      299
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_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  0.0765
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24035
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.149
_diffrn_reflns_theta_min         1.878
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1204 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.8983.
The \l/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.056
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.023
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         5525
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1284
_refine_ls_R_factor_gt           0.0551
_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^)+(0.0572P)^2^+0.2815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1484
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2947
_reflns_number_total             5525
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc02260a2.cif
_cod_data_source_block           mo_gs_ds_1_km_340_3_0m
_cod_database_code               7131841
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.979
_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.a Ternary CH refined with riding coordinates:
 C20(H20), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C12(H12A,H12B), C11(H11A,H11B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3), C10(H10)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C1(H1A,H1B,H1C), C21(H21A,H21B,H21C), C17(H17A,H17B,
 H17C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              46999
_shelx_hkl_checksum              41607
_olex2_exptl_crystal_mounting_method 'Nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'