Complementary mechanochemical and biphasic approaches for the synthesis of organic thiocyanates using hexacyanoferrates as non-toxic cyanide sources.
Grundke, Caroline; Groß, Jonathan; Vierengel, Nina; Sirleaf, Jason; Schmitz, Matthias; Krieger, Leonie; Opatz, Till; Organic & biomolecular chemistry 21 (2023) 644–650; doi:10.1039/d2ob02216h

data_7159045
_publ_section_title
;
 Complementary mechanochemical and biphasic approaches for the synthesis
 of organic thiocyanates using hexacyanoferrates as non-toxic cyanide
 sources.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              644
_journal_page_last               650
_journal_paper_doi               10.1039/d2ob02216h
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C12 H12 Br N3 O3 S, C4 H8 O2'
_chemical_formula_sum            'C16 H20 Br N3 O5 S'
_chemical_formula_weight         446.32
_chemical_name_common            'Psammaplin B'
_chemical_name_systematic
'(E)-3-(3'-bromo-4'-hydroxyphenyl)-2-(hydroxyimino)-N-(2''-thiocyanatoethyl)proppanamide ethyl acetate'
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-09-12 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.337(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9760(12)
_cell_length_b                   6.7233(3)
_cell_length_c                   14.7489(10)
_cell_measurement_reflns_used    13589
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.70
_cell_volume                     1948.7(2)
_computing_cell_refinement       'X-Area Recipe 1.36.0.0 (STOE, 2020)'
_computing_data_collection       'X-Area WinXpose 2.0.22.0 (STOE, 2016)'
_computing_data_reduction        'X-Area Integrate 1.77.0.0 (STOE, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Shelxdrick, 2015)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9405
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.017
_diffrn_reflns_theta_min         2.813
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    2.248
_exptl_absorpt_correction_T_max  0.8995
_exptl_absorpt_correction_T_min  0.5126
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOAc/Penthan'
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.646
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0217P)^2^+4.7807P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0869
_refine_ls_wR_factor_ref         0.0966
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3789
_reflns_number_total             4610
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02216h2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Dual' was changed to
'dual' 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 

 Adding full bibliography for 7159045.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7159045
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.361
_shelx_estimated_absorpt_t_max   0.936
_shelx_res_checksum              3414