Three component hydroxyletherification and hydroxylazidation of (trifluoromethyl)alkenes: access to α-trifluoromethyl β-heteroatom substituted tertiary alcohols.
Zeng, Hao; Zhu, Chuanle; Liu, Chi; Cai, Yingying; Chen, Fulin; Jiang, Huanfeng; Chemical communications (Cambridge, England) 56 (2020) 6241–6244; doi:10.1039/d0cc02550j

data_7126457
_publ_section_title
;
 Three component hydroxyletherification and hydroxylazidation of
 (trifluoromethyl)alkenes: access to \a-trifluoromethyl \b-heteroatom
 substituted tertiary alcohols.
;
_journal_issue                   46
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6241
_journal_page_last               6244
_journal_paper_doi               10.1039/d0cc02550j
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C15 H14 F3 N O2 S'
_chemical_formula_sum            'C15 H14 F3 N O2 S'
_chemical_formula_weight         329.33
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-12-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-27 deposited with the CCDC.	2020-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.176(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.516(3)
_cell_length_b                   5.6738(5)
_cell_length_c                   21.937(2)
_cell_measurement_reflns_used    1197
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.012
_cell_measurement_theta_min      3.022
_cell_volume                     2981.0(5)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_av_unetI/netI     0.1074
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            10820
_diffrn_reflns_theta_full        25.93
_diffrn_reflns_theta_max         25.93
_diffrn_reflns_theta_min         3.02
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0944 before and 0.0594 after correction. The Ratio of minimum to maximum transmission is 0.8634. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1356
_refine_ls_R_factor_gt           0.0621
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0268P)^2^+7.0399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1313
_reflns_number_gt                1630
_reflns_number_total             2829
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d0cc02550j2.cif
_cod_data_source_block           zz
_cod_depositor_comments          'Adding full bibliography for 7126457.cif.'
_cod_database_code               7126457
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C11(H11), C12(H12), C15(H15), C14(H14), C3(H3), C2(H2A), C1(H1)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'