Tetraarylphosphonium salt-catalyzed formal [3+2] cycloaddition between epoxides and trichloroacetonitrile for the synthesis of β-amino alcohol derivatives.
Toda, Yasunori; Shiokawa, Ryota; Iwasaki, Masaya; Yamaguchi, Daisuke; Kawamura, Keisuke; Sukegawa, Kimiya; Suga, Hiroyuki; Chemical communications (Cambridge, England)  (2022) –; doi:10.1039/d2cc03782c

data_7130788
_publ_section_title
;
 Tetraarylphosphonium salt-catalyzed formal [3+2] cycloaddition between
 epoxides and trichloroacetonitrile for the synthesis of \b-amino alcohol
 derivatives.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d2cc03782c
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C11 H12 Cl3 N O3'
_chemical_formula_weight         312.56
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2022-09-12 deposited with the CCDC.	2022-09-22 downloaded from the CCDC.
;
_cell_angle_alpha                80.5156(16)
_cell_angle_beta                 88.5593(16)
_cell_angle_gamma                80.2619(16)
_cell_formula_units_Z            4
_cell_length_a                   5.8297(7)
_cell_length_b                   14.5160(18)
_cell_length_c                   17.059(2)
_cell_measurement_reflns_used    2994
_cell_measurement_temperature    93.(2)
_cell_measurement_theta_max      24.0027
_cell_measurement_theta_min      2.4210
_cell_volume                     1403.3(3)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service v2010.11.0.0'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  'Generate Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      93.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0126
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8423
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         27.72
_diffrn_reflns_theta_min         1.44
_diffrn_source                   'sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.50
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.388
_exptl_crystal_size_min          0.286
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.322
_refine_ls_abs_structure_details
;

Flack x determined using 721 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.250
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         7201
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.249
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0334P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0809
_refine_ls_wR_factor_ref         0.0876
_reflns_Friedel_coverage         0.132
_reflns_Friedel_fraction_full    0.162
_reflns_Friedel_fraction_max     0.127
_reflns_number_gt                5826
_reflns_number_total             7201
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc03782c2.cif
_cod_data_source_block           220725_17RS106_4
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C44 H48 Cl12 N4 O12'
_cod_original_formula_weight         1250.26
_cod_original_formula_units_Z            1
_cod_database_code               7130788
_shelx_res_checksum              82121
_shelx_hkl_checksum              33935