#------------------------------------------------------------------------------
#$Date: 2024-07-05 20:57:11 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293256 $
#$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) . . . . ?