#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:29:23 +0300 (Fri, 05 May 2023) $
#$Revision: 283492 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/90/7159045.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159045
loop_
_publ_author_name
'Grundke, Caroline'
'Groß, Jonathan'
'Vierengel, Nina'
'Sirleaf, Jason'
'Schmitz, Matthias'
'Krieger, Leonie'
'Opatz, Till'
_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 & 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, ω 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/[σ²(Fo²)+(0.0217P)²+4.7807P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.361
_shelx_estimated_absorpt_t_max   0.936
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.57491(17) 0.8306(5) 0.6390(3) 0.0442(8) Uani 1 1 d . . . . .
C2 C 0.60525(17) 0.6886(5) 0.6611(2) 0.0294(7) Uani 1 1 d . . . . .
S3 S 0.64907(4) 0.47819(12) 0.69310(6) 0.02713(17) Uani 1 1 d . . . . .
C4 C 0.57551(17) 0.3158(5) 0.6943(2) 0.0259(6) Uani 1 1 d . . . . .
H4A H 0.5958(19) 0.198(6) 0.714(2) 0.033(7) Uiso 1 1 d . U . . .
H4B H 0.5496(19) 0.364(6) 0.736(3) 0.033(7) Uiso 1 1 d . U . . .
C5 C 0.53352(17) 0.2960(5) 0.5983(2) 0.0277(7) Uani 1 1 d . . . . .
H5A H 0.5167(19) 0.425(6) 0.577(3) 0.034(7) Uiso 1 1 d . U . . .
H5B H 0.5610(19) 0.251(6) 0.556(3) 0.034(7) Uiso 1 1 d . U . . .
N6 N 0.47634(14) 0.1630(4) 0.59747(19) 0.0253(5) Uani 1 1 d . . . . .
H6 H 0.484(2) 0.048(6) 0.602(3) 0.035(11) Uiso 1 1 d . . . . .
C7 C 0.41192(16) 0.2261(5) 0.5842(2) 0.0236(6) Uani 1 1 d . . . . .
O8 O 0.39587(13) 0.4035(3) 0.57851(18) 0.0363(6) Uani 1 1 d . . . . .
C9 C 0.35782(15) 0.0674(5) 0.57676(19) 0.0216(6) Uani 1 1 d . . . . .
N10 N 0.37972(13) -0.1118(4) 0.57602(17) 0.0213(5) Uani 1 1 d . . . . .
O11 O 0.32734(12) -0.2511(4) 0.56738(16) 0.0267(5) Uani 1 1 d . . . . .
H11 H 0.348(3) -0.358(8) 0.569(3) 0.069(17) Uiso 1 1 d . . . . .
C12 C 0.28514(16) 0.1323(5) 0.5697(2) 0.0249(6) Uani 1 1 d . . . . .
H12A H 0.2836(19) 0.239(6) 0.606(3) 0.033(10) Uiso 1 1 d . . . . .
H12B H 0.2607(17) 0.024(5) 0.593(2) 0.023(9) Uiso 1 1 d . . . . .
C13 C 0.25146(15) 0.1808(5) 0.4712(2) 0.0232(6) Uani 1 1 d . . . . .
C14 C 0.25806(15) 0.0506(5) 0.3995(2) 0.0230(6) Uani 1 1 d . . . . .
H14 H 0.2819(16) -0.076(5) 0.414(2) 0.021(8) Uiso 1 1 d . . . . .
C15 C 0.22704(15) 0.0948(5) 0.3098(2) 0.0230(6) Uani 1 1 d . . . . .
Br16 Br 0.23843(2) -0.08463(5) 0.21417(2) 0.02936(10) Uani 1 1 d . . . . .
C17 C 0.18932(15) 0.2687(5) 0.2889(2) 0.0241(6) Uani 1 1 d . . . . .
O18 O 0.15945(12) 0.3032(4) 0.19895(16) 0.0311(5) Uani 1 1 d . . . . .
H18 H 0.143(2) 0.410(7) 0.200(3) 0.047 Uiso 1 1 d . U . . .
C19 C 0.18351(17) 0.3980(5) 0.3603(2) 0.0290(7) Uani 1 1 d . . . . .
H19 H 0.1600(19) 0.514(6) 0.345(3) 0.034(10) Uiso 1 1 d . . . . .
C20 C 0.21462(17) 0.3550(5) 0.4501(2) 0.0280(7) Uani 1 1 d . . . . .
H20 H 0.2115(19) 0.440(6) 0.498(3) 0.039(11) Uiso 1 1 d . . . . .
C1A C 0.0242(2) 0.9544(6) 0.1528(3) 0.0428(9) Uani 1 1 d . . . . .
H1AA H 0.057949 1.061043 0.166680 0.075(9) Uiso 1 1 calc R U . . .
H1AB H 0.002123 0.932539 0.206112 0.075(9) Uiso 1 1 calc R U . . .
H1AC H -0.010044 0.992148 0.099366 0.075(9) Uiso 1 1 calc R U . . .
C2A C 0.05894(17) 0.7668(5) 0.1316(2) 0.0310(7) Uani 1 1 d . . . . .
O3A O 0.07982(13) 0.6407(4) 0.18787(17) 0.0372(6) Uani 1 1 d . . . . .
O4A O 0.06259(14) 0.7530(4) 0.04285(16) 0.0407(6) Uani 1 1 d . . . . .
C5A C 0.0946(2) 0.5739(6) 0.0141(3) 0.0412(9) Uani 1 1 d . . . . .
H5AA H 0.074281 0.453768 0.036942 0.052(9) Uiso 1 1 calc R U . . .
H5AB H 0.144004 0.574561 0.039395 0.052(9) Uiso 1 1 calc R U . . .
C6A C 0.0830(2) 0.5738(6) -0.0885(3) 0.0402(8) Uani 1 1 d . . . . .
H6AA H 0.101481 0.451214 -0.110165 0.052(7) Uiso 1 1 calc R U . . .
H6AB H 0.105758 0.688904 -0.110100 0.052(7) Uiso 1 1 calc R U . . .
H6AC H 0.034031 0.581039 -0.112629 0.052(7) Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C2 S3 179.3(4) . . ?
C2 S3 C4 97.22(16) . . ?
C5 C4 S3 110.7(2) . . ?
C5 C4 H4A 111(2) . . ?
S3 C4 H4A 102(2) . . ?
C5 C4 H4B 112(2) . . ?
S3 C4 H4B 110(2) . . ?
H4A C4 H4B 111(3) . . ?
N6 C5 C4 111.4(3) . . ?
N6 C5 H5A 109(2) . . ?
C4 C5 H5A 109(2) . . ?
N6 C5 H5B 110(2) . . ?
C4 C5 H5B 110(2) . . ?
H5A C5 H5B 106(3) . . ?
C7 N6 C5 122.9(3) . . ?
C7 N6 H6 119(3) . . ?
C5 N6 H6 118(3) . . ?
O8 C7 N6 123.3(3) . . ?
O8 C7 C9 120.3(3) . . ?
N6 C7 C9 116.4(3) . . ?
N10 C9 C12 126.8(3) . . ?
N10 C9 C7 115.1(3) . . ?
C12 C9 C7 118.1(3) . . ?
C9 N10 O11 112.4(2) . . ?
N10 O11 H11 103(4) . . ?
C9 C12 C13 112.6(2) . . ?
C9 C12 H12A 109(2) . . ?
C13 C12 H12A 110(2) . . ?
C9 C12 H12B 107(2) . . ?
C13 C12 H12B 109.8(19) . . ?
H12A C12 H12B 108(3) . . ?
C20 C13 C14 118.5(3) . . ?
C20 C13 C12 121.3(3) . . ?
C14 C13 C12 120.1(3) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.8(19) . . ?
C13 C14 H14 119.0(19) . . ?
C14 C15 C17 121.3(3) . . ?
C14 C15 Br16 118.6(2) . . ?
C17 C15 Br16 120.0(2) . . ?
O18 C17 C19 123.2(3) . . ?
O18 C17 C15 118.6(3) . . ?
C19 C17 C15 118.2(3) . . ?
C17 O18 H18 104(3) . . ?
C17 C19 C20 120.7(3) . . ?
C17 C19 H19 117(2) . . ?
C20 C19 H19 122(2) . . ?
C13 C20 C19 121.2(3) . . ?
C13 C20 H20 117(2) . . ?
C19 C20 H20 121(2) . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
O3A C2A O4A 123.7(3) . . ?
O3A C2A C1A 124.3(3) . . ?
O4A C2A C1A 111.9(3) . . ?
C2A O4A C5A 116.6(3) . . ?
O4A C5A C6A 107.4(3) . . ?
O4A C5A H5AA 110.2 . . ?
C6A C5A H5AA 110.2 . . ?
O4A C5A H5AB 110.2 . . ?
C6A C5A H5AB 110.2 . . ?
H5AA C5A H5AB 108.5 . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
C5A C6A H6AC 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.146(4) . ?
C2 S3 1.686(3) . ?
S3 C4 1.833(3) . ?
C4 C5 1.516(4) . ?
C4 H4A 0.91(4) . ?
C4 H4B 0.93(4) . ?
C5 N6 1.449(4) . ?
C5 H5A 0.96(4) . ?
C5 H5B 0.94(4) . ?
N6 C7 1.336(4) . ?
N6 H6 0.79(4) . ?
C7 O8 1.234(4) . ?
C7 C9 1.509(4) . ?
C9 N10 1.283(4) . ?
C9 C12 1.502(4) . ?
N10 O11 1.393(3) . ?
O11 H11 0.82(5) . ?
C12 C13 1.523(4) . ?
C12 H12A 0.90(4) . ?
C12 H12B 0.97(4) . ?
C13 C20 1.388(4) . ?
C13 C14 1.396(4) . ?
C14 C15 1.390(4) . ?
C14 H14 0.98(3) . ?
C15 C17 1.395(4) . ?
C15 Br16 1.900(3) . ?
C17 O18 1.373(4) . ?
C17 C19 1.387(5) . ?
O18 H18 0.79(4) . ?
C19 C20 1.388(5) . ?
C19 H19 0.92(4) . ?
C20 H20 0.92(4) . ?
C1A C2A 1.499(5) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C2A O3A 1.207(4) . ?
C2A O4A 1.327(4) . ?
O4A C5A 1.461(4) . ?
C5A C6A 1.489(5) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4A N1 0.91(4) 2.71(4) 3.362(5) 129(3) 1_545 yes
C5 H5B N10 0.94(4) 2.63(4) 3.570(4) 171(3) 3_656 yes
N6 H6 N1 0.79(4) 2.32(4) 2.969(4) 140(4) 1_545 yes
O11 H11 O8 0.82(5) 1.86(5) 2.686(3) 177(5) 1_545 yes
C12 H12A Br16 0.90(4) 3.05(4) 3.921(3) 165(3) 4_566 yes
C14 H14 O11 0.98(3) 2.57(3) 3.306(4) 132(2) . yes
O18 H18 O3A 0.79(4) 1.99(5) 2.759(3) 165(4) . yes
C1A H1AA O18 0.98 2.58 3.550(5) 171.6 1_565 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 S3 C4 C5 64.2(3) . . . . ?
S3 C4 C5 N6 178.2(2) . . . . ?
C4 C5 N6 C7 110.0(3) . . . . ?
C5 N6 C7 O8 -5.6(5) . . . . ?
C5 N6 C7 C9 174.7(3) . . . . ?
O8 C7 C9 N10 174.5(3) . . . . ?
N6 C7 C9 N10 -5.8(4) . . . . ?
O8 C7 C9 C12 -4.7(4) . . . . ?
N6 C7 C9 C12 175.1(3) . . . . ?
C12 C9 N10 O11 0.1(4) . . . . ?
C7 C9 N10 O11 -178.9(2) . . . . ?
N10 C9 C12 C13 -94.3(4) . . . . ?
C7 C9 C12 C13 84.7(3) . . . . ?
C9 C12 C13 C20 -132.0(3) . . . . ?
C9 C12 C13 C14 47.0(4) . . . . ?
C20 C13 C14 C15 -1.2(5) . . . . ?
C12 C13 C14 C15 179.7(3) . . . . ?
C13 C14 C15 C17 0.4(5) . . . . ?
C13 C14 C15 Br16 179.1(2) . . . . ?
C14 C15 C17 O18 -179.5(3) . . . . ?
Br16 C15 C17 O18 1.8(4) . . . . ?
C14 C15 C17 C19 0.1(5) . . . . ?
Br16 C15 C17 C19 -178.5(2) . . . . ?
O18 C17 C19 C20 179.7(3) . . . . ?
C15 C17 C19 C20 0.1(5) . . . . ?
C14 C13 C20 C19 1.5(5) . . . . ?
C12 C13 C20 C19 -179.5(3) . . . . ?
C17 C19 C20 C13 -0.9(5) . . . . ?
O3A C2A O4A C5A -0.6(5) . . . . ?
C1A C2A O4A C5A -179.1(3) . . . . ?
C2A O4A C5A C6A 170.8(3) . . . . ?
