Oxidative Esterification of Aldehydes Using Mesoionic 1,2,3-Triazolyl Carbene Organocatalysts.
Berry, Matthew T.; Castrejon, Disnay; Hein, Jason E.; Organic letters 16 (2014) 3676–; doi:10.1021/ol501458p

data_1516774
_publ_section_title
;
 Oxidative Esterification of Aldehydes Using Mesoionic 1,2,3-Triazolyl
 Carbene Organocatalysts.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3676
_journal_paper_doi               10.1021/ol501458p
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C21 H23 Cl N3 O, C2 F6 N O4 S2'
_chemical_formula_sum            'C23 H23 Cl F6 N4 O5 S2'
_chemical_formula_weight         649.02
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-10-16
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.1755(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7957(4)
_cell_length_b                   24.5476(11)
_cell_length_c                   12.6500(5)
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.165
_cell_measurement_theta_min      2.318
_cell_volume                     2715.5(2)
_computing_cell_refinement       'SAINT v8.32B (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.32B (Bruker, 2013)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41773
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.408
_diffrn_reflns_theta_min         1.819
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.379
_exptl_absorpt_correction_T_max  0.2602
_exptl_absorpt_correction_T_min  0.2217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0712 before and 0.0510 after correction. The Ratio of minimum to maximum transmission is 0.8520. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_description       Block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.434
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5562
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0374
_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^)+(0.0296P)^2^+3.1162P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4675
_reflns_number_total             5562
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol501458p_si_001.cif
_cod_data_source_block           Hein02
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1516774.cif.
;
_cod_database_code               1516774
_shelxl_version_number           2013-3
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.922
_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. Restrained distances
 O1B-C6B
 1.45 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C6) = Uanis(C6B)
Uanis(O1B) = Uanis(O1)
4. Others
 Sof(O1B)=Sof(H1B)=Sof(C6B)=Sof(H6B)=1-FVAR(1)
 Sof(O1)=Sof(H1)=Sof(C6)=Sof(H6)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C6(H6), C6B(H6B)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1C), C2(H2A,H2B), C3(H3A,H3B)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C15(H15), C17(H17)
5.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
5.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1B(H1B)
;
_shelx_res_checksum              26233
_shelx_hkl_checksum              47190