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_1547628
_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         'C16 H10 F6 N4 O2 S'
_chemical_formula_sum            'C16 H10 F6 N4 O2 S'
_chemical_formula_weight         436.34
_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   geom
_audit_creation_date             2015-05-28
_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                 93.794(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2715(14)
_cell_length_b                   8.4441(10)
_cell_length_c                   16.4877(19)
_cell_measurement_reflns_used    7131
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      25.03
_cell_measurement_theta_min      2.89
_cell_volume                     1704.7(3)
_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)'
_diffrn_ambient_temperature      122
_diffrn_measured_fraction_theta_full 0.994
_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  0.0702
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22730
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.147
_diffrn_reflns_theta_max         25.147
_diffrn_reflns_theta_min         2.476
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1220 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.8319.
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    1.700
_exptl_crystal_description       prism
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.115
_refine_diff_density_max         1.302
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0575
_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^)+(0.0764P)^2^+3.9500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1435
_refine_ls_wR_factor_ref         0.1555
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2404
_reflns_number_total             3029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7sc03366d2.cif
_cod_data_source_block           mo_d8v1111_0m
_cod_database_code               1547628
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C1(H1A), C3(H3), C6(H6), C8(H8), C9(H9), C14(H14), C15(H15),
 C16(H16)
;
_shelx_res_checksum              16120
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'