#------------------------------------------------------------------------------
#$Date: 2025-01-13 17:52:54 +0200 (Mon, 13 Jan 2025) $
#$Revision: 297302 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/99/7159917.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_7159917
loop_
_publ_author_name
'Wang, Qing'
'Shao, Chukai'
'Hua, Ruirui'
'Yin, Hongquan'
'Chen, Fu-Xue'
_publ_section_title
;
Me3SiBr-promoted cascade electrophilic
thiocyanation/cyclization of ortho-alkynylanilines to synthesize
indole derivatives.
;
_journal_issue 20
_journal_name_full 'Organic & biomolecular chemistry'
_journal_page_first 4031
_journal_page_last 4035
_journal_paper_doi 10.1039/d4ob00367e
_journal_volume 22
_journal_year 2024
_chemical_formula_sum 'C19 H15 Ca N2 O S'
_chemical_formula_weight 359.47
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_Hall '-P 2yn'
_space_group_name_H-M_alt 'P 1 21/n 1'
_atom_sites_solution_hydrogens geom
_audit_creation_method SHELXL-2019/3
_audit_update_record
;
2023-12-22 deposited with the CCDC. 2024-04-25 downloaded from the CCDC.
;
_cell_angle_alpha 90
_cell_angle_beta 102.255(2)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 9.39200(10)
_cell_length_b 12.6535(2)
_cell_length_c 14.9156(2)
_cell_measurement_reflns_used 7890
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 99
_cell_measurement_theta_min 3
_cell_volume 1732.20(4)
_computing_cell_refinement 'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_collection 'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_data_reduction 'CrysAlisPro 1.171.42.59a (Rigaku OD, 2022)'
_computing_structure_refinement 'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature 296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0304
_diffrn_reflns_av_unetI/netI 0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 18
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 16805
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 76.201
_diffrn_reflns_theta_min 4.628
_diffrn_source 'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu 4.304
_exptl_absorpt_correction_T_max 0.999
_exptl_absorpt_correction_T_min 0.666
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.378
_exptl_crystal_description clear_block
_exptl_crystal_F_000 748
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.15
_refine_diff_density_max 0.857
_refine_diff_density_min -0.932
_refine_diff_density_rms 0.097
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.081
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 218
_refine_ls_number_reflns 3506
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.081
_refine_ls_R_factor_all 0.0834
_refine_ls_R_factor_gt 0.0788
_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^)+(0.1639P)^2^+1.1485P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2472
_refine_ls_wR_factor_ref 0.2539
_reflns_Friedel_coverage 0.000
_reflns_number_gt 3143
_reflns_number_total 3506
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file d4ob00367e2.cif
_cod_data_source_block test
_cod_depositor_comments 'Adding full bibliography for 7159917.cif.'
_cod_original_sg_symbol_H-M 'P 21/n'
_cod_database_code 7159917
_shelx_shelxl_version_number 2019/3
_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_res_file
;
TITL samp7423_autored_a.res in P2(1)/n
test.res
created by SHELXL-2019/3 at 17:29:45 on 21-Dec-2023
REM Old TITL samp7423_autored in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.226, Rweak 0.127, Alpha 0.030
REM 2.800 for 177 systematic absences, Orientation as input
REM Formula found by SHELXT: C9 N O3 Cl2
CELL 1.54184 9.392 12.6535 14.9156 90 102.255 90
ZERR 4 0.0001 0.0002 0.0002 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Ca N O S
UNIT 76 60 4 8 4 4
L.S. 55
PLAN 5
TEMP 22.85
CONF
FREE Ca1 C6
FREE Ca1 C8
FREE Ca1 C7
list 4
MORE -1
HTAB
BOND $H
fmap 2
acta
OMIT 1 1 0
REM
REM
REM
WGHT 0.163900 1.148500
FVAR 0.63351
CA1 3 0.827593 -0.054292 0.580745 11.00000 0.06578 0.05704 =
0.06167 0.00211 0.00890 0.01781
S11 6 0.415330 0.332275 0.260960 11.00000 0.07486 0.13637 =
0.05524 0.00341 0.01395 -0.01398
O23 5 -0.009094 0.653928 0.417633 11.00000 0.05709 0.08767 =
0.10752 0.01057 0.00764 0.00180
N2 4 0.438934 0.255885 0.520118 11.00000 0.05477 0.07331 =
0.05504 -0.00421 0.01463 -0.00145
N13 4 0.696531 0.403698 0.250602 11.00000 0.09744 0.25937 =
0.08224 0.02393 0.02145 -0.05559
C3 1 0.386358 0.316835 0.443046 11.00000 0.05331 0.07081 =
0.05509 -0.00034 0.01108 -0.00947
C4 1 0.449951 0.279522 0.372710 11.00000 0.06116 0.08705 =
0.05720 -0.00427 0.01484 -0.01556
C5 1 0.635695 0.130104 0.367543 11.00000 0.07062 0.09472 =
0.07802 -0.02116 0.02508 -0.00674
AFIX 43
H5 2 0.641596 0.137790 0.306429 11.00000 -1.20000
AFIX 0
C6 1 0.716492 0.054959 0.422137 11.00000 0.07331 0.09296 =
0.10233 -0.04039 0.02894 -0.00961
AFIX 43
H6 2 0.778326 0.010977 0.398033 11.00000 -1.20000
AFIX 0
C7 1 0.706416 0.044226 0.513248 11.00000 0.06065 0.07601 =
0.10053 -0.01885 0.01284 -0.00386
C8 1 0.616374 0.106372 0.554117 11.00000 0.06460 0.07295 =
0.07424 -0.01144 0.01129 -0.00534
AFIX 43
H8 2 0.610634 0.097381 0.615131 11.00000 -1.20000
AFIX 0
C9 1 0.535985 0.182109 0.499287 11.00000 0.05284 0.07054 =
0.06676 -0.01102 0.01296 -0.00639
C10 1 0.543540 0.195307 0.406601 11.00000 0.06243 0.07984 =
0.06250 -0.01730 0.02082 -0.01556
C12 1 0.584037 0.375215 0.256521 11.00000 0.09252 0.13099 =
0.06183 0.00446 0.02764 -0.02197
C14 1 0.386398 0.256808 0.605231 11.00000 0.06026 0.08157 =
0.06323 0.00693 0.02105 0.00274
AFIX 23
H14A 2 0.367653 0.184578 0.621204 11.00000 -1.20000
H14B 2 0.294494 0.294596 0.594838 11.00000 -1.20000
AFIX 0
C15 1 0.488522 0.306339 0.684766 11.00000 0.07834 0.09883 =
0.05379 -0.00145 0.01415 0.00992
AFIX 43
H15 2 0.458184 0.308633 0.740171 11.00000 -1.20000
AFIX 0
C16 1 0.616076 0.346634 0.683877 11.00000 0.07935 0.10702 =
0.07345 -0.00941 0.00595 -0.00530
AFIX 93
H16A 2 0.651089 0.346162 0.630048 11.00000 -1.20000
H16B 2 0.671990 0.375828 0.737072 11.00000 -1.20000
AFIX 0
C17 1 0.282043 0.404127 0.441218 11.00000 0.05285 0.07731 =
0.05451 0.00116 0.01197 -0.01019
C18 1 0.305619 0.482772 0.506480 11.00000 0.05251 0.08030 =
0.05848 0.00222 0.00375 -0.00398
AFIX 43
H18 2 0.386787 0.479118 0.554524 11.00000 -1.20000
AFIX 0
C19 1 0.210609 0.567178 0.501820 11.00000 0.05837 0.07625 =
0.06830 -0.00456 0.01185 -0.00555
AFIX 43
H19 2 0.227458 0.619465 0.546646 11.00000 -1.20000
AFIX 0
C20 1 0.088843 0.573321 0.429097 11.00000 0.05341 0.07585 =
0.07291 0.00726 0.01298 -0.00790
C21 1 0.063273 0.492816 0.364890 11.00000 0.05778 0.08740 =
0.07123 0.00533 0.00027 -0.00743
AFIX 43
H21 2 -0.019026 0.494987 0.317562 11.00000 -1.20000
AFIX 0
C22 1 0.157866 0.410609 0.370683 11.00000 0.06346 0.08117 =
0.06337 -0.00313 0.00572 -0.01091
AFIX 43
H22 2 0.139551 0.357433 0.326694 11.00000 -1.20000
AFIX 0
C24 1 0.024782 0.742766 0.473486 11.00000 0.07138 0.07643 =
0.12215 0.00229 0.02312 0.00090
AFIX 137
H24A 2 -0.045331 0.797421 0.452651 11.00000 -1.50000
H24B 2 0.120302 0.767564 0.470589 11.00000 -1.50000
H24C 2 0.022686 0.724446 0.535650 11.00000 -1.50000
AFIX 0
HKLF 4
REM samp7423_autored_a.res in P2(1)/n
REM wR2 = 0.2539, GooF = S = 1.081, Restrained GooF = 1.081 for all data
REM R1 = 0.0788 for 3143 Fo > 4sig(Fo) and 0.0834 for all 3506 data
REM 218 parameters refined using 0 restraints
END
WGHT 0.1636 1.1947
REM No hydrogen bonds found for HTAB generation
REM Highest difference peak 0.857, deepest hole -0.932, 1-sigma level 0.097
Q1 1 0.4568 0.2633 0.2798 11.00000 0.05 0.42
Q2 1 -0.1436 0.5381 0.3249 11.00000 0.05 0.20
Q3 1 0.6903 0.0006 0.5659 11.00000 0.05 0.18
Q4 1 0.5131 0.4032 0.5488 11.00000 0.05 0.17
Q5 1 0.6853 0.3454 0.3129 11.00000 0.05 0.17
;
_shelx_res_checksum 30896
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Ca1 Ca 0.82759(9) -0.05429(6) 0.58075(5) 0.0622(3) Uani 1 1 d . . . . .
S11 S 0.41533(14) 0.33227(14) 0.26096(8) 0.0888(5) Uani 1 1 d . . . . .
O23 O -0.0091(3) 0.6539(3) 0.4176(3) 0.0855(9) Uani 1 1 d . . . . .
N2 N 0.4389(3) 0.2559(3) 0.5201(2) 0.0606(7) Uani 1 1 d . . . . .
N13 N 0.6965(7) 0.4037(8) 0.2506(4) 0.146(3) Uani 1 1 d . . . . .
C3 C 0.3864(4) 0.3168(3) 0.4430(3) 0.0598(9) Uani 1 1 d . . . . .
C4 C 0.4500(4) 0.2795(4) 0.3727(3) 0.0681(10) Uani 1 1 d . . . . .
C5 C 0.6357(5) 0.1301(4) 0.3675(4) 0.0797(12) Uani 1 1 d . . . . .
H5 H 0.641596 0.137790 0.306429 0.096 Uiso 1 1 calc R U . . .
C6 C 0.7165(6) 0.0550(4) 0.4221(4) 0.0880(16) Uani 1 1 d . . . . .
H6 H 0.778326 0.010977 0.398033 0.106 Uiso 1 1 calc R U . . .
C7 C 0.7064(5) 0.0442(4) 0.5132(4) 0.0797(13) Uani 1 1 d . . . . .
C8 C 0.6164(5) 0.1064(4) 0.5541(3) 0.0711(10) Uani 1 1 d . . . . .
H8 H 0.610634 0.097381 0.615131 0.085 Uiso 1 1 calc R U . . .
C9 C 0.5360(4) 0.1821(3) 0.4993(3) 0.0633(9) Uani 1 1 d . . . . .
C10 C 0.5435(4) 0.1953(4) 0.4066(3) 0.0671(10) Uani 1 1 d . . . . .
C12 C 0.5840(6) 0.3752(6) 0.2565(3) 0.0934(16) Uani 1 1 d . . . . .
C14 C 0.3864(4) 0.2568(4) 0.6052(3) 0.0672(10) Uani 1 1 d . . . . .
H14A H 0.367653 0.184578 0.621204 0.081 Uiso 1 1 calc R U . . .
H14B H 0.294494 0.294596 0.594838 0.081 Uiso 1 1 calc R U . . .
C15 C 0.4885(5) 0.3063(4) 0.6848(3) 0.0770(12) Uani 1 1 d . . . . .
H15 H 0.458184 0.308633 0.740171 0.092 Uiso 1 1 calc R U . . .
C16 C 0.6161(6) 0.3466(5) 0.6839(4) 0.0881(14) Uani 1 1 d . . . . .
H16A H 0.651089 0.346162 0.630048 0.106 Uiso 1 1 calc R U . . .
H16B H 0.671990 0.375828 0.737072 0.106 Uiso 1 1 calc R U . . .
C17 C 0.2820(4) 0.4041(3) 0.4412(3) 0.0615(9) Uani 1 1 d . . . . .
C18 C 0.3056(4) 0.4828(4) 0.5065(3) 0.0650(9) Uani 1 1 d . . . . .
H18 H 0.386787 0.479118 0.554524 0.078 Uiso 1 1 calc R U . . .
C19 C 0.2106(5) 0.5672(4) 0.5018(3) 0.0679(10) Uani 1 1 d . . . . .
H19 H 0.227458 0.619465 0.546646 0.081 Uiso 1 1 calc R U . . .
C20 C 0.0888(4) 0.5733(4) 0.4291(3) 0.0675(10) Uani 1 1 d . . . . .
C21 C 0.0633(5) 0.4928(4) 0.3649(3) 0.0741(11) Uani 1 1 d . . . . .
H21 H -0.019026 0.494987 0.317562 0.089 Uiso 1 1 calc R U . . .
C22 C 0.1579(5) 0.4106(4) 0.3707(3) 0.0705(10) Uani 1 1 d . . . . .
H22 H 0.139551 0.357433 0.326694 0.085 Uiso 1 1 calc R U . . .
C24 C 0.0248(6) 0.7428(4) 0.4735(4) 0.0896(15) Uani 1 1 d . . . . .
H24A H -0.045331 0.797421 0.452651 0.134 Uiso 1 1 calc R U . . .
H24B H 0.120302 0.767564 0.470589 0.134 Uiso 1 1 calc R U . . .
H24C H 0.022686 0.724446 0.535650 0.134 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ca1 0.0658(5) 0.0570(5) 0.0617(5) 0.0021(3) 0.0089(4) 0.0178(3)
S11 0.0749(7) 0.1364(12) 0.0552(6) 0.0034(6) 0.0140(5) -0.0140(7)
O23 0.0571(16) 0.088(2) 0.108(3) 0.0106(18) 0.0076(16) 0.0018(14)
N2 0.0548(15) 0.0733(19) 0.0550(16) -0.0042(13) 0.0146(13) -0.0014(14)
N13 0.097(4) 0.259(9) 0.082(3) 0.024(4) 0.021(3) -0.056(5)
C3 0.0533(18) 0.071(2) 0.0551(18) -0.0003(15) 0.0111(15) -0.0095(16)
C4 0.061(2) 0.087(3) 0.057(2) -0.0043(18) 0.0148(16) -0.016(2)
C5 0.071(2) 0.095(3) 0.078(3) -0.021(2) 0.025(2) -0.007(2)
C6 0.073(3) 0.093(4) 0.102(4) -0.040(3) 0.029(3) -0.010(2)
C7 0.061(2) 0.076(3) 0.101(4) -0.019(2) 0.013(2) -0.0039(19)
C8 0.065(2) 0.073(2) 0.074(2) -0.0114(19) 0.0113(19) -0.0053(19)
C9 0.0528(18) 0.071(2) 0.067(2) -0.0110(17) 0.0130(16) -0.0064(16)
C10 0.062(2) 0.080(3) 0.063(2) -0.0173(18) 0.0208(17) -0.0156(19)
C12 0.093(3) 0.131(5) 0.062(2) 0.004(3) 0.028(2) -0.022(3)
C14 0.060(2) 0.082(3) 0.063(2) 0.0069(18) 0.0211(17) 0.0027(18)
C15 0.078(3) 0.099(3) 0.054(2) -0.001(2) 0.0142(19) 0.010(2)
C16 0.079(3) 0.107(4) 0.073(3) -0.009(3) 0.006(2) -0.005(3)
C17 0.0529(18) 0.077(2) 0.0545(18) 0.0012(16) 0.0120(14) -0.0102(17)
C18 0.0525(18) 0.080(2) 0.058(2) 0.0022(18) 0.0038(15) -0.0040(17)
C19 0.058(2) 0.076(2) 0.068(2) -0.0046(18) 0.0118(18) -0.0055(17)
C20 0.0534(19) 0.076(2) 0.073(2) 0.0073(19) 0.0130(17) -0.0079(17)
C21 0.058(2) 0.087(3) 0.071(2) 0.005(2) 0.0003(18) -0.007(2)
C22 0.063(2) 0.081(3) 0.063(2) -0.0031(19) 0.0057(17) -0.011(2)
C24 0.071(3) 0.076(3) 0.122(4) 0.002(3) 0.023(3) 0.001(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Ca Ca 0.3641 1.2855 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C12 S11 C4 99.9(2) . . ?
C20 O23 C24 117.8(4) . . ?
C3 N2 C9 108.9(3) . . ?
C3 N2 C14 126.3(3) . . ?
C9 N2 C14 124.2(4) . . ?
N2 C3 C4 107.5(4) . . ?
N2 C3 C17 123.5(3) . . ?
C4 C3 C17 129.0(4) . . ?
C3 C4 C10 108.7(4) . . ?
C3 C4 S11 124.1(4) . . ?
C10 C4 S11 127.1(3) . . ?
C6 C5 C10 118.1(5) . . ?
C6 C5 H5 120.9 . . ?
C10 C5 H5 120.9 . . ?
C5 C6 C7 120.3(5) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 123.3(5) . . ?
C9 C8 C7 116.2(5) . . ?
C9 C8 H8 121.9 . . ?
C7 C8 H8 121.9 . . ?
C8 C9 N2 129.8(4) . . ?
C8 C9 C10 122.0(4) . . ?
N2 C9 C10 108.2(4) . . ?
C4 C10 C5 133.5(4) . . ?
C4 C10 C9 106.5(3) . . ?
C5 C10 C9 120.0(5) . . ?
N13 C12 S11 177.8(5) . . ?
N2 C14 C15 114.6(4) . . ?
N2 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
N2 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 126.3(4) . . ?
C16 C15 H15 116.9 . . ?
C14 C15 H15 116.9 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C18 C17 C22 118.2(4) . . ?
C18 C17 C3 121.5(3) . . ?
C22 C17 C3 120.2(4) . . ?
C17 C18 C19 121.1(4) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C18 C19 C20 119.6(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
O23 C20 C21 116.9(4) . . ?
O23 C20 C19 123.9(4) . . ?
C21 C20 C19 119.2(4) . . ?
C22 C21 C20 120.3(4) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 121.5(4) . . ?
C21 C22 H22 119.2 . . ?
C17 C22 H22 119.2 . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
S11 C12 1.690(6) . ?
S11 C4 1.761(4) . ?
O23 C20 1.360(6) . ?
O23 C24 1.395(7) . ?
N2 C3 1.385(5) . ?
N2 C9 1.385(5) . ?
N2 C14 1.456(5) . ?
N13 C12 1.137(7) . ?
C3 C4 1.395(6) . ?
C3 C17 1.473(6) . ?
C4 C10 1.405(7) . ?
C5 C6 1.371(8) . ?
C5 C10 1.408(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.387(7) . ?
C8 C9 1.377(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.409(6) . ?
C14 C15 1.496(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.305(8) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9300 . ?
C16 H16B 0.9300 . ?
C17 C18 1.377(6) . ?
C17 C22 1.397(6) . ?
C18 C19 1.384(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.401(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(7) . ?
C21 C22 1.359(7) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
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
C9 N2 C3 C4 0.9(4) . . . . ?
C14 N2 C3 C4 -170.5(4) . . . . ?
C9 N2 C3 C17 -179.1(3) . . . . ?
C14 N2 C3 C17 9.5(6) . . . . ?
N2 C3 C4 C10 -0.4(4) . . . . ?
C17 C3 C4 C10 179.6(4) . . . . ?
N2 C3 C4 S11 179.7(3) . . . . ?
C17 C3 C4 S11 -0.3(6) . . . . ?
C12 S11 C4 C3 117.7(4) . . . . ?
C12 S11 C4 C10 -62.2(5) . . . . ?
C10 C5 C6 C7 0.1(7) . . . . ?
C5 C6 C7 C8 0.3(8) . . . . ?
C6 C7 C8 C9 -0.6(7) . . . . ?
C7 C8 C9 N2 -179.3(4) . . . . ?
C7 C8 C9 C10 0.6(6) . . . . ?
C3 N2 C9 C8 178.9(4) . . . . ?
C14 N2 C9 C8 -9.5(6) . . . . ?
C3 N2 C9 C10 -0.9(4) . . . . ?
C14 N2 C9 C10 170.7(4) . . . . ?
C3 C4 C10 C5 -179.0(5) . . . . ?
S11 C4 C10 C5 0.9(7) . . . . ?
C3 C4 C10 C9 -0.1(4) . . . . ?
S11 C4 C10 C9 179.7(3) . . . . ?
C6 C5 C10 C4 178.5(5) . . . . ?
C6 C5 C10 C9 -0.2(7) . . . . ?
C8 C9 C10 C4 -179.2(4) . . . . ?
N2 C9 C10 C4 0.6(4) . . . . ?
C8 C9 C10 C5 -0.2(6) . . . . ?
N2 C9 C10 C5 179.7(4) . . . . ?
C3 N2 C14 C15 -108.6(5) . . . . ?
C9 N2 C14 C15 81.2(5) . . . . ?
N2 C14 C15 C16 -0.4(8) . . . . ?
N2 C3 C17 C18 51.0(5) . . . . ?
C4 C3 C17 C18 -129.0(5) . . . . ?
N2 C3 C17 C22 -131.0(4) . . . . ?
C4 C3 C17 C22 49.0(6) . . . . ?
C22 C17 C18 C19 -1.1(6) . . . . ?
C3 C17 C18 C19 176.9(4) . . . . ?
C17 C18 C19 C20 -0.5(6) . . . . ?
C24 O23 C20 C21 -171.2(4) . . . . ?
C24 O23 C20 C19 9.7(6) . . . . ?
C18 C19 C20 O23 -178.7(4) . . . . ?
C18 C19 C20 C21 2.2(6) . . . . ?
O23 C20 C21 C22 178.7(4) . . . . ?
C19 C20 C21 C22 -2.2(7) . . . . ?
C20 C21 C22 C17 0.5(7) . . . . ?
C18 C17 C22 C21 1.1(6) . . . . ?
C3 C17 C22 C21 -176.9(4) . . . . ?
loop_
_cod_entry_issue_id
_cod_entry_issue_origin
_cod_entry_issue_severity
_cod_entry_issue_description
_cod_entry_issue_author
_cod_entry_issue_date
1 experiment error
;
The presence of the calcium atom is unexplained in the original publication
as none of the reported compounds nor their synthesis mention calcium atoms
at all. Furthermore, the main text claims that the crystal structures is of
compound 3b while the supplementary PDF file associates it with compound 3c.
Replacing the calcium atom with a hydrogen atom does result in the 3b compound,
however, the distance between the calcium atom and the nearest aromatic carbon
atom is extremely long for a C-H bond (1.84 A) and looks more like C-Cl bond.
For a full discussion, see https://projects.ibt.lt/repositories/issues/1557.
;
'Vaitkus, Antanas' 2025-01-13T17:50:20+02:00