data_global

#==========================================================================

# SUBMISSION DETAILS


_publ_contact_author_name         'Pro. Sheng-Jiao Yan'
_publ_contact_author_address
;
Key Laboratory of Medicinal Chemistry for Natural Resource, 
Ministry of Education, School of Chemical Science and
Technology, Yunnan University, Kunming, 650091, P. R. China
;
_publ_contact_author_email         yansj@ynu.edu.cn
_publ_contact_author_fax          '+86 871 65031633'
_publ_contact_author_phone        '+86 871 65031633'

_publ_requested_journal           ' ACS Combinatorial Science'
_publ_requested_category          ?
_publ_requested_coeditor_name     ?

#==========================================================================

# TITLE AND AUTHOR LIST

_publ_section_title
;

Cascade Reaction of 1,1-Enediamines with 2-Benzylidene-
1H-indene-1,3(2H)-diones: Selective Synthesis of 
Indenodihydropyridine and Indenopyridine Compounds

;

_publ_section_title_footnote
.

loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
' Qin Luo'  .
;Key Laboratory of Medicinal Chemistry for Natural Resource, 
Ministry of Education, School of Chemical Science and
Technology, Yunnan University, Kunming, 650091, P. R. China
;
' Qiang Xiao'  .
;Key Laboratory of Medicinal Chemistry for Natural Resource, 
Ministry of Education, School of Chemical Science and
Technology, Yunnan University, Kunming, 650091, P. R. China
;
' Ling-Bin Kong'  .
;Key Laboratory of Medicinal Chemistry for Natural Resource, 
Ministry of Education, School of Chemical Science and
Technology, Yunnan University, Kunming, 650091, P. R. China
;
'Jun Lin^*^'  .
;Key Laboratory of Medicinal Chemistry for Natural Resource, 
Ministry of Education, School of Chemical Science and
Technology, Yunnan University, Kunming, 650091, P. R. China
;
' Sheng-Jiao Yan ^*^'  .
;Key Laboratory of Medicinal Chemistry for Natural Resource, 
Ministry of Education, School of Chemical Science and
Technology, Yunnan University, Kunming, 650091, P. R. China
;
#==========================================================================  


# TEXT

_publ_section_abstract
;
A concise and environmental friendly route for the synthesis of diverse 
indenodihydro-pyridines (3) via a cascade reaction of 1,1-eneamines (1) 
with benzylidene-1H-indene-1,3(2H)-diones (BIDs) (2) in ethanol media 
has been developed. The targeted compounds were efficiently obtained 
by filtration only, without any further post-treatment. In the one-step 
cascade reaction, C-C and C-N bonds were constructed. In addition, 
when 1,4-dioxane was used as solvent and the mixture of 1,1-eneamines 
(1) was refluxed with benzylidene-1H-indene-1,3(2H)-diones (BIDs) (2) for 
about 12 hours, indenopyridine compounds (4) were produced. Two kinds 
of indenopyridine derivatives 3-4 were obtained through alternative solvents 
and temperatures. The reaction has the following features: mild temperature, 
atom economy, high yields, and potential biological activity of the product.
;  

data_mo_0319_7_0m
_audit_creation_date               2018-03-21
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.02.02 svn.r3481 for OlexSys, GUI svn.r5480)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.
Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C26 H18 Cl N3 O3, C2 H6 O S'
_chemical_formula_sum              'C28 H24 Cl N3 O4 S'
_chemical_formula_weight           534.01
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0030 0.0020 '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'
 'Cl' 'Cl' 0.1480 0.1590 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S' 'S' 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
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'

_cell_length_a                     12.2079(8)
_cell_length_b                     9.6867(6)
_cell_length_c                     21.9929(15)
_cell_angle_alpha                  90
_cell_angle_beta                   95.115(3)
_cell_angle_gamma                  90
_cell_volume                       2590.4(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      6976
_cell_measurement_temperature      298.01
_cell_measurement_theta_max        26.39
_cell_measurement_theta_min        2.30
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.268
_exptl_absorpt_correction_T_max    0.7454
_exptl_absorpt_correction_T_min    0.6230
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0683 before and 0.0543 after correction. The Ratio of minimum to maximum transmission is 0.8358. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.369
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1112
_exptl_crystal_size_max            0.28
_exptl_crystal_size_mid            0.26
_exptl_crystal_size_min            0.24
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0657
_diffrn_reflns_av_unetI/netI       0.0395
_diffrn_reflns_Laue_measured_fraction_full  0.994
_diffrn_reflns_Laue_measured_fraction_max  0.993
_diffrn_reflns_limit_h_max         15
_diffrn_reflns_limit_h_min         -15
_diffrn_reflns_limit_k_max         12
_diffrn_reflns_limit_k_min         -12
_diffrn_reflns_limit_l_max         27
_diffrn_reflns_limit_l_min         -27
_diffrn_reflns_number              34050
_diffrn_reflns_point_group_measured_fraction_full  0.994
_diffrn_reflns_point_group_measured_fraction_max  0.993
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           26.440
_diffrn_reflns_theta_min           2.299
_diffrn_ambient_temperature        298.01
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.994
_diffrn_measured_fraction_theta_max  0.993
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_special_details            ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  3273
_reflns_number_total               5308
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.599
_refine_diff_density_min           -0.663
_refine_diff_density_rms           0.051
_refine_ls_extinction_coef         0.0060(10)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref     1.025
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       337
_refine_ls_number_reflns           5308
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.1035
_refine_ls_R_factor_gt             0.0570
_refine_ls_restrained_S_all        1.025
_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)+(0.0714P)²+1.8645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1404
_refine_ls_wR_factor_ref           0.1686
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C25(H25), C3(H3A), C21(H21), C2(H2), C13(H13), C26(H26), C22(H22),
 C24(H24), C16(H16), C14(H14), C23(H23), C15(H15)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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
 Cl1 Cl 0.30053(8) 0.62456(11) 0.08026(4) 0.0789(3) Uani 1 1 d . . . . .
 O3 O 0.62473(18) 0.3012(3) 0.24269(10) 0.0647(6) Uani 1 1 d . . . . .
 O1 O 0.21977(17) 0.4860(3) 0.33164(11) 0.0678(7) Uani 1 1 d . . . . .
 O2 O 0.2724(2) 0.5948(3) 0.41344(11) 0.0817(8) Uani 1 1 d . . . . .
 N2 N 0.52342(17) 0.3039(2) 0.44657(9) 0.0377(5) Uani 1 1 d . . . . .
 N3 N 0.37751(19) 0.3989(2) 0.48985(9) 0.0409(5) Uani 1 1 d . . . . .
 H3 H 0.3190 0.4486 0.4875 0.049 Uiso 1 1 d R . . . .
 N1 N 0.28666(18) 0.5075(2) 0.37484(10) 0.0435(6) Uani 1 1 d . . . . .
 C7 C 0.4288(2) 0.3784(3) 0.43944(11) 0.0353(6) Uani 1 1 d . . . . .
 C6 C 0.3879(2) 0.4277(3) 0.38052(11) 0.0350(6) Uani 1 1 d . . . . .
 C4 C 0.4052(2) 0.4581(3) 0.26715(11) 0.0366(6) Uani 1 1 d . . . . .
 C5 C 0.4428(2) 0.4025(3) 0.32872(11) 0.0357(6) Uani 1 1 d . . . . .
 C8 C 0.5750(2) 0.2833(3) 0.39738(12) 0.0369(6) Uani 1 1 d . . . . .
 C12 C 0.6794(2) 0.2069(3) 0.39662(13) 0.0406(6) Uani 1 1 d . . . . .
 C9 C 0.5404(2) 0.3273(3) 0.33845(12) 0.0381(6) Uani 1 1 d . . . . .
 C19 C 0.4234(2) 0.1344(3) 0.61734(12) 0.0420(6) Uani 1 1 d . . . . .
 C10 C 0.6224(2) 0.2809(3) 0.29649(13) 0.0454(7) Uani 1 1 d . . . . .
 C11 C 0.7078(2) 0.2024(3) 0.33674(14) 0.0447(7) Uani 1 1 d . . . . .
 C17 C 0.4171(2) 0.3400(3) 0.54890(12) 0.0428(7) Uani 1 1 d . . . . .
 H17A H 0.3904 0.3957 0.5811 0.051 Uiso 1 1 calc R . . . .
 H17B H 0.4968 0.3435 0.5534 0.051 Uiso 1 1 calc R . . . .
 C20 C 0.3671(2) 0.1535(3) 0.66825(13) 0.0471(7) Uani 1 1 d . . . . .
 H20 H 0.3018 0.2036 0.6649 0.056 Uiso 1 1 calc R . . . .
 C1 C 0.3415(2) 0.5590(3) 0.15257(12) 0.0467(7) Uani 1 1 d . . . . .
 C25 C 0.4047(2) 0.5980(3) 0.25642(12) 0.0455(7) Uani 1 1 d . . . . .
 H25 H 0.4263 0.6586 0.2880 0.055 Uiso 1 1 calc R . . . .
 C3 C 0.3728(2) 0.3683(3) 0.21936(12) 0.0456(7) Uani 1 1 d . . . . .
 H3A H 0.3730 0.2736 0.2263 0.055 Uiso 1 1 calc R . . . .
 C21 C 0.4057(3) 0.0997(3) 0.72421(13) 0.0523(8) Uani 1 1 d . . . . .
 H21 H 0.3659 0.1126 0.7579 0.063 Uiso 1 1 calc R . . . .
 C2 C 0.3403(2) 0.4188(3) 0.16196(13) 0.0491(7) Uani 1 1 d . . . . .
 H2 H 0.3180 0.3590 0.1301 0.059 Uiso 1 1 calc R . . . .
 C13 C 0.7441(2) 0.1442(3) 0.44334(15) 0.0523(8) Uani 1 1 d . . . . .
 H13 H 0.7266 0.1496 0.4836 0.063 Uiso 1 1 calc R . . . .
 C26 C 0.3721(2) 0.6493(3) 0.19869(13) 0.0506(7) Uani 1 1 d . . . . .
 H26 H 0.3712 0.7439 0.1915 0.061 Uiso 1 1 calc R . . . .
 C18 C 0.3804(3) 0.1920(3) 0.55625(13) 0.0516(8) Uani 1 1 d . . . . .
 H18A H 0.3007 0.1881 0.5524 0.062 Uiso 1 1 calc R . . . .
 H18B H 0.4067 0.1359 0.5241 0.062 Uiso 1 1 calc R . . . .
 C22 C 0.5020(3) 0.0276(3) 0.73033(14) 0.0544(8) Uani 1 1 d . . . . .
 H22 H 0.5278 -0.0091 0.7680 0.065 Uiso 1 1 calc R . . . .
 C24 C 0.5216(3) 0.0623(3) 0.62449(16) 0.0584(8) Uani 1 1 d . . . . .
 H24 H 0.5619 0.0492 0.5910 0.070 Uiso 1 1 calc R . . . .
 C16 C 0.7991(2) 0.1309(3) 0.32165(16) 0.0569(8) Uani 1 1 d . . . . .
 H16 H 0.8172 0.1268 0.2815 0.068 Uiso 1 1 calc R . . . .
 C14 C 0.8366(3) 0.0725(3) 0.42789(18) 0.0632(9) Uani 1 1 d . . . . .
 H14 H 0.8815 0.0284 0.4583 0.076 Uiso 1 1 calc R . . . .
 C23 C 0.5605(3) 0.0096(3) 0.68054(17) 0.0630(9) Uani 1 1 d . . . . .
 H23 H 0.6268 -0.0383 0.6846 0.076 Uiso 1 1 calc R . . . .
 C15 C 0.8627(3) 0.0657(3) 0.36774(19) 0.0639(9) Uani 1 1 d . . . . .
 H15 H 0.9243 0.0162 0.3585 0.077 Uiso 1 1 calc R . . . .
 S1 S 0.12714(9) 0.46030(14) 0.59006(6) 0.0945(4) Uani 1 1 d . . . . .
 O4 O 0.1646(2) 0.4709(4) 0.52774(15) 0.1072(11) Uani 1 1 d . . . . .
 C27 C 0.0251(4) 0.5853(5) 0.5944(2) 0.0937(13) Uani 1 1 d . . . . .
 H27A H 0.0571 0.6756 0.5921 0.141 Uiso 1 1 calc GR . . . .
 H27B H -0.0075 0.5758 0.6323 0.141 Uiso 1 1 calc GR . . . .
 H27C H -0.0304 0.5734 0.5610 0.141 Uiso 1 1 calc GR . . . .
 C28 C 0.0380(5) 0.3160(5) 0.5887(3) 0.137(2) Uani 1 1 d . . . . .
 H28A H -0.0222 0.3299 0.5581 0.206 Uiso 1 1 calc GR . . . .
 H28B H 0.0103 0.3055 0.6279 0.206 Uiso 1 1 calc GR . . . .
 H28C H 0.0777 0.2344 0.5792 0.206 Uiso 1 1 calc GR . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
 Cl1 C1 1.744(3) . ?
 O3 C10 1.203(3) . ?
 O1 N1 1.214(3) . ?
 O2 N1 1.222(3) . ?
 N2 C7 1.359(3) . ?
 N2 C8 1.315(3) . ?
 N3 H3 0.8591 . ?
 N3 C7 1.336(3) . ?
 N3 C17 1.461(3) . ?
 N1 C6 1.453(3) . ?
 C7 C6 1.429(3) . ?
 C6 C5 1.394(3) . ?
 C4 C5 1.491(3) . ?
 C4 C25 1.376(4) . ?
 C4 C3 1.394(4) . ?
 C5 C9 1.397(4) . ?
 C8 C12 1.475(4) . ?
 C8 C9 1.394(4) . ?
 C12 C11 1.392(4) . ?
 C12 C13 1.379(4) . ?
 C9 C10 1.490(4) . ?
 C19 C20 1.378(4) . ?
 C19 C18 1.505(4) . ?
 C19 C24 1.384(4) . ?
 C10 C11 1.511(4) . ?
 C11 C16 1.378(4) . ?
 C17 H17A 0.9700 . ?
 C17 H17B 0.9700 . ?
 C17 C18 1.515(4) . ?
 C20 H20 0.9300 . ?
 C20 C21 1.380(4) . ?
 C1 C2 1.374(4) . ?
 C1 C26 1.366(4) . ?
 C25 H25 0.9300 . ?
 C25 C26 1.388(4) . ?
 C3 H3A 0.9300 . ?
 C3 C2 1.379(4) . ?
 C21 H21 0.9300 . ?
 C21 C22 1.364(4) . ?
 C2 H2 0.9300 . ?
 C13 H13 0.9300 . ?
 C13 C14 1.394(4) . ?
 C26 H26 0.9300 . ?
 C18 H18A 0.9700 . ?
 C18 H18B 0.9700 . ?
 C22 H22 0.9300 . ?
 C22 C23 1.371(5) . ?
 C24 H24 0.9300 . ?
 C24 C23 1.379(4) . ?
 C16 H16 0.9300 . ?
 C16 C15 1.374(5) . ?
 C14 H14 0.9300 . ?
 C14 C15 1.390(5) . ?
 C23 H23 0.9300 . ?
 C15 H15 0.9300 . ?
 S1 O4 1.486(3) . ?
 S1 C27 1.746(4) . ?
 S1 C28 1.770(5) . ?
 C27 H27A 0.9600 . ?
 C27 H27B 0.9600 . ?
 C27 H27C 0.9600 . ?
 C28 H28A 0.9600 . ?
 C28 H28B 0.9600 . ?
 C28 H28C 0.9600 . ?

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
 C8 N2 C7 116.8(2) . . ?
 C7 N3 H3 118.8 . . ?
 C7 N3 C17 122.5(2) . . ?
 C17 N3 H3 118.7 . . ?
 O1 N1 O2 122.3(2) . . ?
 O1 N1 C6 118.9(2) . . ?
 O2 N1 C6 118.8(2) . . ?
 N2 C7 C6 120.5(2) . . ?
 N3 C7 N2 116.1(2) . . ?
 N3 C7 C6 123.4(2) . . ?
 C7 C6 N1 118.8(2) . . ?
 C5 C6 N1 119.3(2) . . ?
 C5 C6 C7 121.8(2) . . ?
 C25 C4 C5 120.5(2) . . ?
 C25 C4 C3 119.2(2) . . ?
 C3 C4 C5 120.2(2) . . ?
 C6 C5 C4 123.2(2) . . ?
 C6 C5 C9 115.6(2) . . ?
 C9 C5 C4 121.1(2) . . ?
 N2 C8 C12 124.3(2) . . ?
 N2 C8 C9 126.2(2) . . ?
 C9 C8 C12 109.5(2) . . ?
 C11 C12 C8 108.3(2) . . ?
 C13 C12 C8 130.5(3) . . ?
 C13 C12 C11 121.1(3) . . ?
 C5 C9 C10 132.3(2) . . ?
 C8 C9 C5 119.1(2) . . ?
 C8 C9 C10 108.6(2) . . ?
 C20 C19 C18 121.0(3) . . ?
 C20 C19 C24 117.7(3) . . ?
 C24 C19 C18 121.2(3) . . ?
 O3 C10 C9 129.5(3) . . ?
 O3 C10 C11 125.7(3) . . ?
 C9 C10 C11 104.8(2) . . ?
 C12 C11 C10 108.8(2) . . ?
 C16 C11 C12 121.2(3) . . ?
 C16 C11 C10 130.0(3) . . ?
 N3 C17 H17A 109.0 . . ?
 N3 C17 H17B 109.0 . . ?
 N3 C17 C18 112.8(2) . . ?
 H17A C17 H17B 107.8 . . ?
 C18 C17 H17A 109.0 . . ?
 C18 C17 H17B 109.0 . . ?
 C19 C20 H20 119.4 . . ?
 C19 C20 C21 121.2(3) . . ?
 C21 C20 H20 119.4 . . ?
 C2 C1 Cl1 119.4(2) . . ?
 C26 C1 Cl1 118.8(2) . . ?
 C26 C1 C2 121.8(3) . . ?
 C4 C25 H25 119.8 . . ?
 C4 C25 C26 120.4(3) . . ?
 C26 C25 H25 119.8 . . ?
 C4 C3 H3A 119.7 . . ?
 C2 C3 C4 120.5(3) . . ?
 C2 C3 H3A 119.7 . . ?
 C20 C21 H21 119.8 . . ?
 C22 C21 C20 120.3(3) . . ?
 C22 C21 H21 119.8 . . ?
 C1 C2 C3 118.8(3) . . ?
 C1 C2 H2 120.6 . . ?
 C3 C2 H2 120.6 . . ?
 C12 C13 H13 121.3 . . ?
 C12 C13 C14 117.4(3) . . ?
 C14 C13 H13 121.3 . . ?
 C1 C26 C25 119.1(3) . . ?
 C1 C26 H26 120.4 . . ?
 C25 C26 H26 120.4 . . ?
 C19 C18 C17 111.3(2) . . ?
 C19 C18 H18A 109.4 . . ?
 C19 C18 H18B 109.4 . . ?
 C17 C18 H18A 109.4 . . ?
 C17 C18 H18B 109.4 . . ?
 H18A C18 H18B 108.0 . . ?
 C21 C22 H22 120.3 . . ?
 C21 C22 C23 119.5(3) . . ?
 C23 C22 H22 120.3 . . ?
 C19 C24 H24 119.5 . . ?
 C23 C24 C19 120.9(3) . . ?
 C23 C24 H24 119.5 . . ?
 C11 C16 H16 121.0 . . ?
 C15 C16 C11 118.0(3) . . ?
 C15 C16 H16 121.0 . . ?
 C13 C14 H14 119.5 . . ?
 C15 C14 C13 121.0(3) . . ?
 C15 C14 H14 119.5 . . ?
 C22 C23 C24 120.3(3) . . ?
 C22 C23 H23 119.8 . . ?
 C24 C23 H23 119.8 . . ?
 C16 C15 C14 121.2(3) . . ?
 C16 C15 H15 119.4 . . ?
 C14 C15 H15 119.4 . . ?
 O4 S1 C27 106.4(2) . . ?
 O4 S1 C28 106.1(3) . . ?
 C27 S1 C28 96.2(2) . . ?
 S1 C27 H27A 109.5 . . ?
 S1 C27 H27B 109.5 . . ?
 S1 C27 H27C 109.5 . . ?
 H27A C27 H27B 109.5 . . ?
 H27A C27 H27C 109.5 . . ?
 H27B C27 H27C 109.5 . . ?
 S1 C28 H28A 109.5 . . ?
 S1 C28 H28B 109.5 . . ?
 S1 C28 H28C 109.5 . . ?
 H28A C28 H28B 109.5 . . ?
 H28A C28 H28C 109.5 . . ?
 H28B C28 H28C 109.5 . . ?

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
 Cl1 C1 C2 C3 -179.9(2) . . . . ?
 Cl1 C1 C26 C25 179.9(2) . . . . ?
 O3 C10 C11 C12 176.9(3) . . . . ?
 O3 C10 C11 C16 -5.1(5) . . . . ?
 O1 N1 C6 C7 -138.7(3) . . . . ?
 O1 N1 C6 C5 41.9(4) . . . . ?
 O2 N1 C6 C7 42.0(4) . . . . ?
 O2 N1 C6 C5 -137.4(3) . . . . ?
 N2 C7 C6 N1 -179.8(2) . . . . ?
 N2 C7 C6 C5 -0.4(4) . . . . ?
 N2 C8 C12 C11 178.3(2) . . . . ?
 N2 C8 C12 C13 -0.5(5) . . . . ?
 N2 C8 C9 C5 1.1(4) . . . . ?
 N2 C8 C9 C10 -179.4(2) . . . . ?
 N3 C7 C6 N1 1.6(4) . . . . ?
 N3 C7 C6 C5 -179.0(2) . . . . ?
 N3 C17 C18 C19 179.6(2) . . . . ?
 N1 C6 C5 C4 2.4(4) . . . . ?
 N1 C6 C5 C9 178.9(2) . . . . ?
 C7 N2 C8 C12 179.0(2) . . . . ?
 C7 N2 C8 C9 -1.9(4) . . . . ?
 C7 N3 C17 C18 -83.0(3) . . . . ?
 C7 C6 C5 C4 -177.0(2) . . . . ?
 C7 C6 C5 C9 -0.5(4) . . . . ?
 C6 C5 C9 C8 0.2(4) . . . . ?
 C6 C5 C9 C10 -179.2(3) . . . . ?
 C4 C5 C9 C8 176.8(2) . . . . ?
 C4 C5 C9 C10 -2.6(4) . . . . ?
 C4 C25 C26 C1 -0.6(4) . . . . ?
 C4 C3 C2 C1 0.6(4) . . . . ?
 C5 C4 C25 C26 178.5(2) . . . . ?
 C5 C4 C3 C2 -178.5(3) . . . . ?
 C5 C9 C10 O3 2.0(5) . . . . ?
 C5 C9 C10 C11 -179.4(3) . . . . ?
 C8 N2 C7 N3 -179.8(2) . . . . ?
 C8 N2 C7 C6 1.5(4) . . . . ?
 C8 C12 C11 C10 1.7(3) . . . . ?
 C8 C12 C11 C16 -176.5(3) . . . . ?
 C8 C12 C13 C14 176.6(3) . . . . ?
 C8 C9 C10 O3 -177.4(3) . . . . ?
 C8 C9 C10 C11 1.2(3) . . . . ?
 C12 C8 C9 C5 -179.7(2) . . . . ?
 C12 C8 C9 C10 -0.2(3) . . . . ?
 C12 C11 C16 C15 -1.0(4) . . . . ?
 C12 C13 C14 C15 0.5(5) . . . . ?
 C9 C8 C12 C11 -0.9(3) . . . . ?
 C9 C8 C12 C13 -179.7(3) . . . . ?
 C9 C10 C11 C12 -1.7(3) . . . . ?
 C9 C10 C11 C16 176.2(3) . . . . ?
 C19 C20 C21 C22 0.9(5) . . . . ?
 C19 C24 C23 C22 0.2(5) . . . . ?
 C10 C11 C16 C15 -178.8(3) . . . . ?
 C11 C12 C13 C14 -2.0(4) . . . . ?
 C11 C16 C15 C14 -0.6(5) . . . . ?
 C17 N3 C7 N2 -2.7(4) . . . . ?
 C17 N3 C7 C6 175.9(2) . . . . ?
 C20 C19 C18 C17 86.2(3) . . . . ?
 C20 C19 C24 C23 1.0(5) . . . . ?
 C20 C21 C22 C23 0.4(5) . . . . ?
 C25 C4 C5 C6 64.9(4) . . . . ?
 C25 C4 C5 C9 -111.4(3) . . . . ?
 C25 C4 C3 C2 -0.1(4) . . . . ?
 C3 C4 C5 C6 -116.7(3) . . . . ?
 C3 C4 C5 C9 67.0(3) . . . . ?
 C3 C4 C25 C26 0.1(4) . . . . ?
 C21 C22 C23 C24 -0.9(5) . . . . ?
 C2 C1 C26 C25 1.1(4) . . . . ?
 C13 C12 C11 C10 -179.4(3) . . . . ?
 C13 C12 C11 C16 2.4(4) . . . . ?
 C13 C14 C15 C16 0.8(5) . . . . ?
 C26 C1 C2 C3 -1.1(4) . . . . ?
 C18 C19 C20 C21 179.3(3) . . . . ?
 C18 C19 C24 C23 -179.9(3) . . . . ?
 C24 C19 C20 C21 -1.6(4) . . . . ?
 C24 C19 C18 C17 -92.9(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'
