#=============================================================================
data_global
loop_
_journal_name_full                 'European Journal of Chemistry'
_journal_coden_ASTM                EJCUA9
_journal_volume                    15
_journal_issue                     4
_journal_year                      2024
_journal_page_first                320
_journal_page_last                 324
#=============================================================================  
data_bmy156_0m
_audit_creation_date               2024-10-17
_audit_creation_method
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_chemical_name_common              ?
_chemical_name_systematic
;
 N-(3-Chloropropionyl)-N'-(4-Methoxyphenyl)thiourea 
;
_chemical_formula_moiety           'C11 H13 Cl N2 O2 S'
_chemical_formula_sum              'C11 H13 Cl N2 O2 S'
_chemical_formula_weight           272.74
_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' 0.0033 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'
 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system        'triclinic'
_space_group_IT_number             2
_space_group_name_H-M_alt          'P -1'
_space_group_name_Hall             '-P 1'
loop_
  _space_group_symop_id
  _space_group_symop_operation_xyz
 1 'x, y, z'
 2 '-x, -y, -z'

_cell_length_a                     10.2262(6)
_cell_length_b                     11.5007(7)
_cell_length_c                     12.6116(8)
_cell_angle_alpha                  72.253(2)
_cell_angle_beta                   66.348(2)
_cell_angle_gamma                  88.099(2)
_cell_volume                       1287.22(14)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      6434
_cell_measurement_temperature      296(2)
_cell_measurement_theta_max        28.4
_cell_measurement_theta_min        3.02
_exptl_absorpt_coefficient_mu      0.450
_exptl_absorpt_correction_T_max    0.8768
_exptl_absorpt_correction_T_min    0.8062
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS (Bruker, 2009)'
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.407
_exptl_crystal_density_meas        'not measured'
_exptl_crystal_density_method      'not measured'
_exptl_crystal_description         block
_exptl_crystal_F_000               568
_exptl_crystal_size_max            0.5
_exptl_crystal_size_mid            0.32
_exptl_crystal_size_min            0.3
_exptl_special_details
;
 ? 
;
_diffrn_reflns_av_R_equivalents    0.0360
_diffrn_reflns_av_unetI/netI       0.0275
_diffrn_reflns_limit_h_max         13
_diffrn_reflns_limit_h_min         -13
_diffrn_reflns_limit_k_max         15
_diffrn_reflns_limit_k_min         -15
_diffrn_reflns_limit_l_max         16
_diffrn_reflns_limit_l_min         -16
_diffrn_reflns_number              33072
_diffrn_reflns_theta_full          28.40
_diffrn_reflns_theta_max           28.40
_diffrn_reflns_theta_min           3.02
_diffrn_ambient_temperature        296(2)
_diffrn_detector_area_resol_mean   83.66
_diffrn_measured_fraction_theta_full  0.995
_diffrn_measured_fraction_theta_max  0.995
_diffrn_measurement_device_type
;
Bruker SMART APEX CCD area-detector diffractometer
;
_diffrn_measurement_method         '\w scan'
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'fine-focus sealed tube'
_reflns_number_gt                  4763
_reflns_number_total               6434
_reflns_threshold_expression       >2sigma(I)
_computing_cell_refinement         'SAINT (Bruker, 2009)'
_computing_data_collection         'SMART (Bruker, 2009)'
_computing_data_reduction          SAINT
_computing_molecular_graphics      'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution      'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max           0.461
_refine_diff_density_min           -0.368
_refine_diff_density_rms           0.080
_refine_ls_extinction_coef         ?
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.069
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       325
_refine_ls_number_reflns           6434
_refine_ls_number_restraints       4
_refine_ls_R_factor_all            0.0837
_refine_ls_R_factor_gt             0.0572
_refine_ls_restrained_S_all        1.069
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'calc w=1/[\s^2^(Fo^2^)+(0.0499P)^2^+1.6566P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1281
_refine_ls_wR_factor_ref           0.1508
_refine_special_details
;
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H1A(0.05) H1B(0.05) H2A(0.049) H2B(0.049) H6(0.069) H7(0.079)
 H9(0.063) H10(0.053) H11A(0.165) H11B(0.165) H11C(0.165) H12A(0.054)
 H12B(0.054) H13A(0.046) H13B(0.046) H17(0.05) H18(0.055) H20(0.056) H21(0.05)
 H22A(0.113) H22B(0.113) H22C(0.113)
 Fixed X: H1A(0.7255) H1B(0.8337) H2A(0.831) H2B(0.9436) H6(0.6047) H7(0.4342)
 H9(0.1665) H10(0.3358) H11A(0.1984) H11B(0.0929) H11C(0.259) H12A(0.2851)
 H12B(0.221) H13A(0.0322) H13B(0.0798) H17(0.399) H18(0.5435) H20(0.6329)
 H21(0.4851) H22A(0.7006) H22B(0.813) H22C(0.8334)
 Fixed Y: H1A(1.1172) H1B(1.0179) H2A(1.176) H2B(1.0806) H6(0.6087) H7(0.4773)
 H9(0.7363) H10(0.8682) H11A(0.3648) H11B(0.3649) H11C(0.388) H12A(0.6203)
 H12B(0.587) H13A(0.7034) H13B(0.7269) H17(1.1128) H18(1.2779) H20(1.4)
 H21(1.2346) H22A(1.5744) H22B(1.5996) H22C(1.4985)
 Fixed Z: H1A(-0.0183) H1B(-0.0402) H2A(0.0932) H2B(0.0684) H6(0.5525)
 H7(0.7334) H9(0.749) H10(0.5713) H11A(0.847) H11B(0.9778) H11C(0.9358)
 H12A(0.4897) H12B(0.4073) H13A(0.4657) H13B(0.562) H17(-0.0247) H18(-0.1859)
 H20(0.045) H21(0.2075) H22A(-0.1165) H22B(-0.2516) H22C(-0.145)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       direct
_atom_sites_solution_secondary     difmap
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_symmetry_multiplicity
  _atom_site_calc_flag
  _atom_site_refinement_flags
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 C1 C 0.8224(3) 1.0983(3) -0.0295(2) 0.0415(6) Uani 1 1 d . . .
 H1A H 0.7255 1.1172 -0.0183 0.050 Uiso 1 1 calc R . .
 H1B H 0.8337 1.0179 -0.0402 0.050 Uiso 1 1 calc R . .
 C2 C 0.8455(3) 1.0964(3) 0.0811(2) 0.0411(6) Uani 1 1 d . . .
 H2A H 0.8310 1.1760 0.0932 0.049 Uiso 1 1 calc R . .
 H2B H 0.9436 1.0806 0.0684 0.049 Uiso 1 1 calc R . .
 C3 C 0.7435(3) 0.9987(2) 0.1937(2) 0.0372(5) Uani 1 1 d . . .
 C4 C 0.7076(3) 0.8865(2) 0.4070(2) 0.0348(5) Uani 1 1 d . . .
 C5 C 0.4865(3) 0.7511(2) 0.5439(2) 0.0374(5) Uani 1 1 d . . .
 C6 C 0.5165(3) 0.6349(3) 0.5919(3) 0.0576(8) Uani 1 1 d . . .
 H6 H 0.6047 0.6087 0.5525 0.069 Uiso 1 1 calc R . .
 C7 C 0.4141(4) 0.5562(3) 0.7002(3) 0.0660(10) Uani 1 1 d . . .
 H7 H 0.4342 0.4773 0.7334 0.079 Uiso 1 1 calc R . .
 C8 C 0.2838(3) 0.5946(3) 0.7577(3) 0.0544(8) Uani 1 1 d . . .
 C9 C 0.2549(3) 0.7102(3) 0.7098(3) 0.0521(7) Uani 1 1 d . . .
 H9 H 0.1665 0.7363 0.7490 0.063 Uiso 1 1 calc R . .
 C10 C 0.3560(3) 0.7890(3) 0.6032(3) 0.0438(6) Uani 1 1 d . . .
 H10 H 0.3358 0.8682 0.5713 0.053 Uiso 1 1 calc R . .
 C11 C 0.1819(6) 0.4014(4) 0.9097(5) 0.1101(19) Uani 1 1 d . . .
 H11A H 0.1984 0.3648 0.8470 0.165 Uiso 1 1 calc R . .
 H11B H 0.0929 0.3649 0.9778 0.165 Uiso 1 1 calc R . .
 H11C H 0.2590 0.3880 0.9358 0.165 Uiso 1 1 calc R . .
 C12 C 0.1965(3) -0.3962(2) 0.4835(3) 0.0450(6) Uani 1 1 d . . .
 H12A H 0.2851 -0.3797 0.4897 0.054 Uiso 1 1 calc R . .
 H12B H 0.2210 -0.4130 0.4073 0.054 Uiso 1 1 calc R . .
 C13 C 0.1145(3) -0.2846(2) 0.4825(2) 0.0387(6) Uani 1 1 d . . .
 H13A H 0.0322 -0.2966 0.4657 0.046 Uiso 1 1 calc R . .
 H13B H 0.0798 -0.2731 0.5620 0.046 Uiso 1 1 calc R . .
 C14 C 0.2103(2) -0.1724(2) 0.3864(2) 0.0327(5) Uani 1 1 d . . .
 C15 C 0.2022(2) 0.0359(2) 0.2577(2) 0.0300(5) Uani 1 1 d . . .
 C16 C 0.4266(2) 0.1593(2) 0.1071(2) 0.0330(5) Uani 1 1 d . . .
 C17 C 0.4451(3) 0.1711(2) -0.0105(2) 0.0413(6) Uani 1 1 d . . .
 H17 H 0.3990 0.1128 -0.0247 0.050 Uiso 1 1 calc R . .
 C18 C 0.5319(3) 0.2694(3) -0.1068(3) 0.0457(6) Uani 1 1 d . . .
 H18 H 0.5435 0.2779 -0.1859 0.055 Uiso 1 1 calc R . .
 C19 C 0.6018(3) 0.3554(2) -0.0856(3) 0.0424(6) Uani 1 1 d . . .
 C20 C 0.5853(3) 0.3428(2) 0.0309(3) 0.0464(6) Uani 1 1 d . . .
 H20 H 0.6329 0.4000 0.0450 0.056 Uiso 1 1 calc R . .
 C21 C 0.4966(3) 0.2435(2) 0.1283(2) 0.0419(6) Uani 1 1 d . . .
 H21 H 0.4851 0.2346 0.2075 0.050 Uiso 1 1 calc R . .
 C22 C 0.7642(4) 0.5375(3) -0.1740(4) 0.0753(12) Uani 1 1 d . . .
 H22A H 0.7006 0.5744 -0.1165 0.113 Uiso 1 1 calc R . .
 H22B H 0.8130 0.5996 -0.2516 0.113 Uiso 1 1 calc R . .
 H22C H 0.8334 0.4985 -0.1450 0.113 Uiso 1 1 calc R . .
 N1 N 0.7820(2) 0.9682(2) 0.29057(19) 0.0353(4) Uani 1 1 d D . .
 N2 N 0.5829(2) 0.8329(2) 0.4286(2) 0.0414(5) Uani 1 1 d D . .
 N3 N 0.1411(2) -0.07523(18) 0.34915(19) 0.0327(4) Uani 1 1 d D . .
 N4 N 0.3438(2) 0.05368(19) 0.20614(19) 0.0356(5) Uani 1 1 d D . .
 O1 O 0.6356(2) 0.9544(2) 0.19738(18) 0.0567(6) Uani 1 1 d . . .
 O2 O 0.1756(3) 0.5260(3) 0.8642(2) 0.0861(9) Uani 1 1 d . . .
 O3 O 0.34096(19) -0.16932(17) 0.34614(18) 0.0455(5) Uani 1 1 d . . .
 O4 O 0.6839(2) 0.44854(19) -0.1874(2) 0.0619(6) Uani 1 1 d . . .
 S1 S 0.77664(8) 0.86728(8) 0.50994(6) 0.0490(2) Uani 1 1 d . . .
 S2 S 0.09416(7) 0.13686(6) 0.22018(7) 0.04584(19) Uani 1 1 d . . .
 Cl1 Cl 0.94719(10) 1.20954(8) -0.16120(7) 0.0635(2) Uani 1 1 d . . .
 Cl2 Cl 0.09484(10) -0.52642(7) 0.60695(8) 0.0621(2) Uani 1 1 d . . .
 H1 H 0.8639(17) 1.002(2) 0.278(3) 0.038(7) Uiso 1 1 d D . .
 H3 H 0.0477(11) -0.089(3) 0.387(3) 0.053(9) Uiso 1 1 d D . .
 H2 H 0.559(3) 0.851(3) 0.367(2) 0.057(10) Uiso 1 1 d D . .
 H4 H 0.390(3) -0.003(2) 0.236(3) 0.045(8) Uiso 1 1 d D . .

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
 C1 0.0378(13) 0.0455(14) 0.0354(13) -0.0073(11) -0.0127(11) -0.0033(11)
 C2 0.0353(13) 0.0465(14) 0.0358(13) -0.0036(11) -0.0149(11) -0.0086(11)
 C3 0.0297(12) 0.0421(13) 0.0346(12) -0.0044(10) -0.0132(10) -0.0025(10)
 C4 0.0298(12) 0.0373(12) 0.0334(12) -0.0072(10) -0.0123(10) 0.0032(9)
 C5 0.0300(12) 0.0411(13) 0.0371(12) -0.0027(10) -0.0165(10) -0.0041(10)
 C6 0.0377(15) 0.0494(17) 0.068(2) 0.0007(15) -0.0186(14) 0.0062(13)
 C7 0.066(2) 0.0461(17) 0.072(2) 0.0084(16) -0.0339(19) -0.0011(15)
 C8 0.0449(16) 0.065(2) 0.0424(15) -0.0001(14) -0.0179(13) -0.0140(14)
 C9 0.0403(15) 0.071(2) 0.0413(15) -0.0193(14) -0.0115(12) 0.0029(14)
 C10 0.0440(15) 0.0447(15) 0.0431(14) -0.0134(12) -0.0188(12) 0.0035(12)
 C11 0.121(4) 0.089(3) 0.083(3) 0.025(3) -0.039(3) -0.047(3)
 C12 0.0423(14) 0.0356(13) 0.0430(14) -0.0015(11) -0.0108(12) -0.0055(11)
 C13 0.0305(12) 0.0359(13) 0.0393(13) 0.0023(10) -0.0137(10) -0.0058(10)
 C14 0.0297(12) 0.0327(11) 0.0324(11) -0.0034(9) -0.0142(9) -0.0039(9)
 C15 0.0297(11) 0.0287(11) 0.0321(11) -0.0048(9) -0.0162(9) -0.0040(9)
 C16 0.0264(11) 0.0313(11) 0.0345(12) 0.0000(9) -0.0132(9) -0.0013(9)
 C17 0.0407(14) 0.0409(14) 0.0418(14) -0.0060(11) -0.0207(11) -0.0080(11)
 C18 0.0477(15) 0.0470(15) 0.0348(13) -0.0047(11) -0.0148(12) -0.0030(12)
 C19 0.0346(13) 0.0325(12) 0.0429(14) -0.0001(10) -0.0069(11) -0.0032(10)
 C20 0.0462(15) 0.0362(13) 0.0498(16) -0.0092(12) -0.0149(13) -0.0107(11)
 C21 0.0428(14) 0.0407(14) 0.0372(13) -0.0076(11) -0.0140(11) -0.0065(11)
 C22 0.059(2) 0.0448(18) 0.081(3) -0.0058(17) 0.0037(18) -0.0181(15)
 N1 0.0262(10) 0.0420(11) 0.0337(10) -0.0044(9) -0.0132(8) -0.0056(8)
 N2 0.0326(11) 0.0487(13) 0.0362(11) 0.0008(10) -0.0169(9) -0.0076(9)
 N3 0.0254(10) 0.0313(10) 0.0373(10) -0.0026(8) -0.0143(8) -0.0037(8)
 N4 0.0266(10) 0.0331(10) 0.0396(11) 0.0024(8) -0.0158(9) -0.0029(8)
 O1 0.0434(11) 0.0748(15) 0.0425(11) 0.0047(10) -0.0232(9) -0.0221(10)
 O2 0.0721(17) 0.094(2) 0.0555(15) 0.0119(14) -0.0138(13) -0.0276(15)
 O3 0.0273(9) 0.0427(10) 0.0508(11) 0.0053(8) -0.0150(8) -0.0028(7)
 O4 0.0586(13) 0.0449(12) 0.0498(12) 0.0064(9) -0.0045(10) -0.0163(10)
 S1 0.0388(4) 0.0683(5) 0.0356(3) -0.0047(3) -0.0184(3) -0.0087(3)
 S2 0.0333(3) 0.0352(3) 0.0616(4) -0.0012(3) -0.0223(3) 0.0007(2)
 Cl1 0.0658(5) 0.0656(5) 0.0381(4) -0.0022(3) -0.0095(3) -0.0167(4)
 Cl2 0.0683(5) 0.0395(4) 0.0601(5) 0.0083(3) -0.0245(4) -0.0121(3)

_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
 C1 H1A 0.9700 . ?
 C1 H1B 0.9700 . ?
 C1 C2 1.501(4) . ?
 C1 Cl1 1.771(3) . ?
 C2 H2A 0.9700 . ?
 C2 H2B 0.9700 . ?
 C2 C3 1.511(3) . ?
 C3 N1 1.374(3) . ?
 C3 O1 1.209(3) . ?
 C4 N1 1.388(3) . ?
 C4 N2 1.324(3) . ?
 C4 S1 1.669(3) . ?
 C5 C6 1.369(4) . ?
 C5 C10 1.374(4) . ?
 C5 N2 1.431(3) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.394(4) . ?
 C7 H7 0.9300 . ?
 C7 C8 1.370(5) . ?
 C8 C9 1.360(5) . ?
 C8 O2 1.368(4) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.379(4) . ?
 C10 H10 0.9300 . ?
 C11 H11A 0.9600 . ?
 C11 H11B 0.9600 . ?
 C11 H11C 0.9600 . ?
 C11 O2 1.381(6) . ?
 C12 H12A 0.9700 . ?
 C12 H12B 0.9700 . ?
 C12 C13 1.509(4) . ?
 C12 Cl2 1.769(3) . ?
 C13 H13A 0.9700 . ?
 C13 H13B 0.9700 . ?
 C13 C14 1.507(3) . ?
 C14 N3 1.365(3) . ?
 C14 O3 1.221(3) . ?
 C15 N3 1.389(3) . ?
 C15 N4 1.321(3) . ?
 C15 S2 1.671(2) . ?
 C16 C17 1.381(4) . ?
 C16 C21 1.371(4) . ?
 C16 N4 1.431(3) . ?
 C17 H17 0.9300 . ?
 C17 C18 1.381(4) . ?
 C18 H18 0.9300 . ?
 C18 C19 1.386(4) . ?
 C19 C20 1.371(4) . ?
 C19 O4 1.363(3) . ?
 C20 H20 0.9300 . ?
 C20 C21 1.398(4) . ?
 C21 H21 0.9300 . ?
 C22 H22A 0.9600 . ?
 C22 H22B 0.9600 . ?
 C22 H22C 0.9600 . ?
 C22 O4 1.421(4) . ?
 N1 H1 0.870(10) . ?
 N2 H2 0.878(10) . ?
 N3 H3 0.874(10) . ?
 N4 H4 0.873(10) . ?

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
 H1A C1 H1B 108.1 . . ?
 C2 C1 H1A 109.6 . . ?
 C2 C1 H1B 109.6 . . ?
 C2 C1 Cl1 110.29(18) . . ?
 Cl1 C1 H1A 109.6 . . ?
 Cl1 C1 H1B 109.6 . . ?
 C1 C2 H2A 109.4 . . ?
 C1 C2 H2B 109.4 . . ?
 C1 C2 C3 111.0(2) . . ?
 H2A C2 H2B 108.0 . . ?
 C3 C2 H2A 109.4 . . ?
 C3 C2 H2B 109.4 . . ?
 N1 C3 C2 114.4(2) . . ?
 O1 C3 C2 121.9(2) . . ?
 O1 C3 N1 123.7(2) . . ?
 N1 C4 S1 118.62(18) . . ?
 N2 C4 N1 116.4(2) . . ?
 N2 C4 S1 124.91(19) . . ?
 C6 C5 C10 119.7(3) . . ?
 C6 C5 N2 122.1(3) . . ?
 C10 C5 N2 118.1(2) . . ?
 C5 C6 H6 120.2 . . ?
 C5 C6 C7 119.6(3) . . ?
 C7 C6 H6 120.2 . . ?
 C6 C7 H7 119.9 . . ?
 C8 C7 C6 120.2(3) . . ?
 C8 C7 H7 119.9 . . ?
 C9 C8 C7 119.9(3) . . ?
 C9 C8 O2 114.7(3) . . ?
 O2 C8 C7 125.4(3) . . ?
 C8 C9 H9 119.9 . . ?
 C8 C9 C10 120.3(3) . . ?
 C10 C9 H9 119.9 . . ?
 C5 C10 C9 120.3(3) . . ?
 C5 C10 H10 119.8 . . ?
 C9 C10 H10 119.8 . . ?
 H11A C11 H11B 109.5 . . ?
 H11A C11 H11C 109.5 . . ?
 H11B C11 H11C 109.5 . . ?
 O2 C11 H11A 109.5 . . ?
 O2 C11 H11B 109.5 . . ?
 O2 C11 H11C 109.5 . . ?
 H12A C12 H12B 108.0 . . ?
 C13 C12 H12A 109.3 . . ?
 C13 C12 H12B 109.3 . . ?
 C13 C12 Cl2 111.47(19) . . ?
 Cl2 C12 H12A 109.3 . . ?
 Cl2 C12 H12B 109.3 . . ?
 C12 C13 H13A 109.6 . . ?
 C12 C13 H13B 109.6 . . ?
 H13A C13 H13B 108.2 . . ?
 C14 C13 C12 110.1(2) . . ?
 C14 C13 H13A 109.6 . . ?
 C14 C13 H13B 109.6 . . ?
 N3 C14 C13 115.5(2) . . ?
 O3 C14 C13 121.6(2) . . ?
 O3 C14 N3 122.8(2) . . ?
 N3 C15 S2 118.78(17) . . ?
 N4 C15 N3 116.7(2) . . ?
 N4 C15 S2 124.56(17) . . ?
 C17 C16 N4 120.0(2) . . ?
 C21 C16 C17 120.3(2) . . ?
 C21 C16 N4 119.5(2) . . ?
 C16 C17 H17 120.0 . . ?
 C18 C17 C16 119.9(2) . . ?
 C18 C17 H17 120.0 . . ?
 C17 C18 H18 120.0 . . ?
 C17 C18 C19 120.0(3) . . ?
 C19 C18 H18 120.0 . . ?
 C20 C19 C18 120.1(2) . . ?
 O4 C19 C18 114.8(3) . . ?
 O4 C19 C20 125.1(3) . . ?
 C19 C20 H20 120.1 . . ?
 C19 C20 C21 119.7(3) . . ?
 C21 C20 H20 120.1 . . ?
 C16 C21 C20 119.9(2) . . ?
 C16 C21 H21 120.0 . . ?
 C20 C21 H21 120.0 . . ?
 H22A C22 H22B 109.5 . . ?
 H22A C22 H22C 109.5 . . ?
 H22B C22 H22C 109.5 . . ?
 O4 C22 H22A 109.5 . . ?
 O4 C22 H22B 109.5 . . ?
 O4 C22 H22C 109.5 . . ?
 C3 N1 C4 127.9(2) . . ?
 C3 N1 H1 117.0(19) . . ?
 C4 N1 H1 115.1(19) . . ?
 C4 N2 C5 125.2(2) . . ?
 C4 N2 H2 116(2) . . ?
 C5 N2 H2 119(2) . . ?
 C14 N3 C15 127.5(2) . . ?
 C14 N3 H3 114(2) . . ?
 C15 N3 H3 119(2) . . ?
 C15 N4 C16 125.1(2) . . ?
 C15 N4 H4 117(2) . . ?
 C16 N4 H4 118(2) . . ?
 C8 O2 C11 119.7(4) . . ?
 C19 O4 C22 118.2(3) . . ?

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
 C1 C2 C3 N1 163.2(2) . . . . ?
 C1 C2 C3 O1 -18.5(4) . . . . ?
 C2 C3 N1 C4 176.9(2) . . . . ?
 C5 C6 C7 C8 0.4(6) . . . . ?
 C6 C5 C10 C9 -0.8(4) . . . . ?
 C6 C5 N2 C4 -71.0(4) . . . . ?
 C6 C7 C8 C9 -0.6(5) . . . . ?
 C6 C7 C8 O2 -179.7(3) . . . . ?
 C7 C8 C9 C10 0.1(5) . . . . ?
 C7 C8 O2 C11 -12.4(6) . . . . ?
 C8 C9 C10 C5 0.6(4) . . . . ?
 C9 C8 O2 C11 168.5(4) . . . . ?
 C10 C5 C6 C7 0.3(5) . . . . ?
 C10 C5 N2 C4 113.3(3) . . . . ?
 C12 C13 C14 N3 160.0(2) . . . . ?
 C12 C13 C14 O3 -20.8(4) . . . . ?
 C13 C14 N3 C15 -176.0(2) . . . . ?
 C16 C17 C18 C19 0.8(4) . . . . ?
 C17 C16 C21 C20 1.0(4) . . . . ?
 C17 C16 N4 C15 -77.5(3) . . . . ?
 C17 C18 C19 C20 0.2(4) . . . . ?
 C17 C18 C19 O4 -179.7(3) . . . . ?
 C18 C19 C20 C21 -0.6(4) . . . . ?
 C18 C19 O4 C22 -177.2(3) . . . . ?
 C19 C20 C21 C16 0.0(4) . . . . ?
 C20 C19 O4 C22 2.9(4) . . . . ?
 C21 C16 C17 C18 -1.4(4) . . . . ?
 C21 C16 N4 C15 107.7(3) . . . . ?
 N1 C4 N2 C5 -176.5(2) . . . . ?
 N2 C4 N1 C3 -1.5(4) . . . . ?
 N2 C5 C6 C7 -175.3(3) . . . . ?
 N2 C5 C10 C9 175.0(2) . . . . ?
 N3 C15 N4 C16 177.1(2) . . . . ?
 N4 C15 N3 C14 -5.1(4) . . . . ?
 N4 C16 C17 C18 -176.2(2) . . . . ?
 N4 C16 C21 C20 175.8(2) . . . . ?
 O1 C3 N1 C4 -1.4(5) . . . . ?
 O2 C8 C9 C10 179.3(3) . . . . ?
 O3 C14 N3 C15 4.7(4) . . . . ?
 O4 C19 C20 C21 179.3(3) . . . . ?
 S1 C4 N1 C3 -178.9(2) . . . . ?
 S1 C4 N2 C5 0.8(4) . . . . ?
 S2 C15 N3 C14 174.8(2) . . . . ?
 S2 C15 N4 C16 -2.8(4) . . . . ?
 Cl1 C1 C2 C3 -177.93(19) . . . . ?
 Cl2 C12 C13 C14 172.91(18) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'