Thiosemicarbazone organocatalysis: tetrahydropyranylation and 2-deoxygalactosylation reactions and kinetics-based mechanistic investigation
Larsen, Dennis; Langhorn, Line M.; Akselsen, Olivia M.; Nielsen, Bjarne E.; Pittelkow, Michael; Chem. Sci.  (2017) –; doi:10.1039/C7SC03366D

data_1547630
_publ_section_title
;
 Thiosemicarbazone organocatalysis: tetrahydropyranylation and
 2-deoxygalactosylation reactions and kinetics-based mechanistic
 investigation
;
_journal_name_full               'Chem. Sci.'
_journal_paper_doi               10.1039/C7SC03366D
_journal_year                    2017
_chemical_formula_moiety         'C18 H13 F6 N3 O2 S'
_chemical_formula_sum            'C18 H13 F6 N3 O2 S'
_chemical_formula_weight         449.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-04-13 deposited with the CCDC.
2017-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.897(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2731(16)
_cell_length_b                   9.2592(14)
_cell_length_c                   16.180(3)
_cell_measurement_reflns_used    9835
_cell_measurement_temperature    100(30)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.53
_cell_volume                     1837.7(5)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker Instrument Service'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_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  0.0585
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22131
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.479
_diffrn_reflns_theta_min         2.519
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.257
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6720
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1321 before and 0.0773 after correction.
The Ratio of minimum to maximum transmission is 0.9015.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       cube
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.481
_exptl_crystal_size_mid          0.338
_exptl_crystal_size_min          0.325
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0300P)^2^+1.3410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.0907
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3274
_reflns_number_total             3785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03366d2.cif
_cod_data_source_block           mo_d8v1154_0m
_cod_database_code               1547630
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C16(H16), C17(H17), C19(H19), C20(H20), C23(H23), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_shelx_res_checksum              46502
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'