# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_cu_csh250_0m
_database_code_depnum_ccdc_archive 'CCDC 1563998'
_audit_update_record             
;
2017-07-23 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_audit_creation_date             2017-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H14 N2 O6, 2(C2 H6 O S)'
_chemical_formula_sum            'C31 H26 N2 O8 S2'
_chemical_formula_weight         618.66
_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 0.0181 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'
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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.102(7)
_cell_length_b                   8.688(3)
_cell_length_c                   18.461(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.011(7)
_cell_angle_gamma                90
_cell_volume                     2716.3(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3020
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.28
_cell_measurement_theta_min      4.84
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.528
_exptl_absorpt_coefficient_mu    2.286
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6049
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1051 before and 0.0657 after correction. The Ratio of minimum to maximum transmission is 0.8032. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            13190
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.147
_diffrn_reflns_theta_min         4.838
_diffrn_ambient_temperature      99.98
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1973
_reflns_number_total             2481
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2481
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1051P)²+0.9485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1450
_refine_ls_wR_factor_ref         0.1584
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 S2-O5 \\sim S1-O4 \\sim S3-O6
 with sigma of 0.01
 S2-C20 \\sim S3-C17 \\sim S1-C15 \\sim S2-C18 \\sim S3-C19 \\sim S1-C16
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C18) = Uanis(C19)
Uanis(C20) = Uanis(C17)
Uanis(O4) = Uanis(O5) = Uanis(O6)
4. Others
 Fixed Sof: H13A(0.5) H13B(0.5) S1(0.5) S2(0.25) S3(0.25) O4(0.5) O5(0.25)
 O6(0.25) C15(0.5) H15A(0.5) H15B(0.5) H15C(0.5) C16(0.5) H16A(0.5) H16B(0.5)
 H16C(0.5) C17(0.25) H17A(0.25) H17B(0.25) H17C(0.25) C18(0.25) H18A(0.25)
 H18B(0.25) H18C(0.25) C19(0.25) H19A(0.25) H19B(0.25) H19C(0.25) C20(0.25)
 H20A(0.25) H20B(0.25) H20C(0.25)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C9(H9)
5.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O1 O 0.67139(13) 0.8355(2) 0.55048(11) 0.0623(5) Uani 1 1 d . . . . .
N1 N 0.44379(11) 0.3743(2) 0.70199(10) 0.0395(4) Uani 1 1 d . . . . .
C1 C 0.48135(18) 0.8316(3) 0.45020(13) 0.0538(7) Uani 1 1 d . . . . .
O2 O 0.56001(13) 0.8628(2) 0.47535(9) 0.0584(5) Uani 1 1 d . . . . .
C2 C 0.43935(16) 0.7229(3) 0.49251(12) 0.0480(6) Uani 1 1 d . . . . .
O3 O 0.45319(15) 0.8971(2) 0.39535(9) 0.0648(6) Uani 1 1 d . . . . .
C3 C 0.36086(17) 0.6882(3) 0.46959(12) 0.0514(6) Uani 1 1 d . . . . .
H3 H 0.3335 0.7358 0.4271 0.062 Uiso 1 1 calc R . . . .
C4 C 0.32188(16) 0.5824(3) 0.50949(13) 0.0499(6) Uani 1 1 d . . . . .
H4 H 0.2681 0.5576 0.4936 0.060 Uiso 1 1 calc R . . . .
C5 C 0.36113(14) 0.5138(3) 0.57189(12) 0.0445(5) Uani 1 1 d . . . . .
H5 H 0.3341 0.4415 0.5980 0.053 Uiso 1 1 calc R . . . .
C6 C 0.44084(14) 0.5497(2) 0.59731(12) 0.0409(5) Uani 1 1 d . . . . .
C7 C 0.48392(13) 0.4815(2) 0.66180(11) 0.0388(5) Uani 1 1 d . . . . .
C8 C 0.56319(14) 0.5171(2) 0.68286(12) 0.0404(5) Uani 1 1 d . . . . .
C9 C 0.60112(14) 0.6213(2) 0.64137(13) 0.0432(5) Uani 1 1 d . . . . .
H9 H 0.6552 0.6452 0.6562 0.052 Uiso 1 1 calc R . . . .
C10 C 0.56173(15) 0.6896(2) 0.57950(12) 0.0448(5) Uani 1 1 d . . . . .
C11 C 0.60376(17) 0.7974(3) 0.53735(13) 0.0522(6) Uani 1 1 d . . . . .
C12 C 0.48097(15) 0.6555(2) 0.55642(12) 0.0429(5) Uani 1 1 d . . . . .
C13 C 0.5000 0.2801(3) 0.7500 0.0415(7) Uani 1 2 d S T P . .
H13A H 0.5293 0.2131 0.7198 0.050 Uiso 0.5 1 calc R . . . .
H13B H 0.4707 0.2131 0.7802 0.050 Uiso 0.5 1 calc R . . . .
C14 C 0.39066(13) 0.4494(3) 0.74816(12) 0.0414(5) Uani 1 1 d . . . . .
H14A H 0.3524 0.3729 0.7618 0.050 Uiso 1 1 calc R . . . .
H14B H 0.3606 0.5322 0.7199 0.050 Uiso 1 1 calc R . . . .
S1 S 0.34296(6) -0.11829(14) 0.65381(6) 0.0375(3) Uani 0.5 1 d D . . A 1
S2 S 0.28972(14) -0.0814(3) 0.69193(13) 0.0490(6) Uani 0.25 1 d D . . B 2
S3 S 0.34080(12) -0.1456(2) 0.70896(12) 0.0351(4) Uani 0.25 1 d D . . C 3
O4 O 0.2863(6) -0.2123(9) 0.6916(8) 0.0476(11) Uani 0.5 1 d D . . A 1
O5 O 0.2747(11) -0.2520(13) 0.6924(14) 0.0476(11) Uani 0.25 1 d D . . B 2
O6 O 0.2611(6) -0.2120(18) 0.6826(10) 0.0476(11) Uani 0.25 1 d D . . C 3
C15 C 0.3194(3) 0.0809(5) 0.6610(3) 0.0431(10) Uani 0.5 1 d D . . A 1
H15A H 0.2746 0.1068 0.6239 0.065 Uiso 0.5 1 calc GR . . A 1
H15B H 0.3652 0.1434 0.6531 0.065 Uiso 0.5 1 calc GR . . A 1
H15C H 0.3056 0.1017 0.7098 0.065 Uiso 0.5 1 calc GR . . A 1
C16 C 0.4322(3) -0.1143(5) 0.7176(2) 0.0408(9) Uani 0.5 1 d D . . A 1
H16A H 0.4219 -0.0654 0.7632 0.061 Uiso 0.5 1 calc GR . . A 1
H16B H 0.4726 -0.0555 0.6967 0.061 Uiso 0.5 1 calc GR . . A 1
H16C H 0.4509 -0.2197 0.7278 0.061 Uiso 0.5 1 calc GR . . A 1
C17 C 0.325(3) -0.009(6) 0.7775(18) 0.048(3) Uani 0.25 1 d D . . C 3
H17A H 0.2902 0.0731 0.7553 0.071 Uiso 0.25 1 calc GR . . C 3
H17B H 0.3752 0.0341 0.7995 0.071 Uiso 0.25 1 calc GR . . C 3
H17C H 0.2992 -0.0608 0.8154 0.071 Uiso 0.25 1 calc GR . . C 3
C18 C 0.3736(9) -0.040(4) 0.6485(15) 0.057(4) Uani 0.25 1 d D . . B 2
H18A H 0.3781 0.0717 0.6425 0.085 Uiso 0.25 1 calc GR . . B 2
H18B H 0.3678 -0.0897 0.6005 0.085 Uiso 0.25 1 calc GR . . B 2
H18C H 0.4212 -0.0788 0.6787 0.085 Uiso 0.25 1 calc GR . . B 2
C19 C 0.3483(11) -0.009(3) 0.6394(15) 0.057(4) Uani 0.25 1 d D . . C 3
H19A H 0.3619 -0.0611 0.5959 0.085 Uiso 0.25 1 calc GR . . C 3
H19B H 0.3895 0.0663 0.6567 0.085 Uiso 0.25 1 calc GR . . C 3
H19C H 0.2976 0.0444 0.6272 0.085 Uiso 0.25 1 calc GR . . C 3
C20 C 0.326(3) -0.022(6) 0.7827(17) 0.048(3) Uani 0.25 1 d D . . B 2
H20A H 0.3787 -0.0665 0.7974 0.071 Uiso 0.25 1 calc GR . . B 2
H20B H 0.2902 -0.0569 0.8161 0.071 Uiso 0.25 1 calc GR . . B 2
H20C H 0.3300 0.0907 0.7844 0.071 Uiso 0.25 1 calc GR . . B 2


_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
O1 C11 1.195(3) . ?
N1 C7 1.425(3) . ?
N1 C13 1.463(3) . ?
N1 C14 1.481(3) . ?
C1 O2 1.387(4) . ?
C1 C2 1.474(3) . ?
C1 O3 1.202(3) . ?
O2 C11 1.398(3) . ?
C2 C3 1.383(4) . ?
C2 C12 1.417(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.403(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.413(3) . ?
C6 C7 1.438(3) . ?
C6 C12 1.425(3) . ?
C7 C8 1.392(3) . ?
C8 C9 1.401(3) . ?
C8 C14 1.520(3) 2_656 ?
C9 H9 0.9500 . ?
C9 C10 1.377(3) . ?
C10 C11 1.468(3) . ?
C10 C12 1.419(4) . ?
C13 N1 1.463(3) 2_656 ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C8 1.520(3) 2_656 ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
S1 O4 1.510(8) . ?
S1 C15 1.785(4) . ?
S1 C16 1.794(4) . ?
S2 O5 1.504(9) . ?
S2 C18 1.775(13) . ?
S2 C20 1.781(16) . ?
S3 O6 1.497(8) . ?
S3 C17 1.782(16) . ?
S3 C19 1.768(13) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
C7 N1 C13 110.94(16) . . ?
C7 N1 C14 112.95(16) . . ?
C13 N1 C14 107.56(15) . . ?
O2 C1 C2 118.0(2) . . ?
O3 C1 O2 116.4(2) . . ?
O3 C1 C2 125.6(3) . . ?
C1 O2 C11 125.29(19) . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 C12 121.2(2) . . ?
C12 C2 C1 118.7(2) . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 122.9(2) . . ?
C5 C6 C12 118.7(2) . . ?
C12 C6 C7 118.4(2) . . ?
N1 C7 C6 118.2(2) . . ?
C8 C7 N1 121.4(2) . . ?
C8 C7 C6 120.4(2) . . ?
C7 C8 C9 119.9(2) . . ?
C7 C8 C14 121.30(19) . 2_656 ?
C9 C8 C14 118.8(2) . 2_656 ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 C12 120.1(2) . . ?
C12 C10 C11 120.1(2) . . ?
O1 C11 O2 116.5(2) . . ?
O1 C11 C10 126.9(3) . . ?
O2 C11 C10 116.6(2) . . ?
C2 C12 C6 119.0(2) . . ?
C2 C12 C10 121.2(2) . . ?
C10 C12 C6 119.8(2) . . ?
N1 C13 N1 112.0(2) . 2_656 ?
N1 C13 H13A 109.2 . . ?
N1 C13 H13A 109.2 2_656 . ?
N1 C13 H13B 109.2 . . ?
N1 C13 H13B 109.2 2_656 . ?
H13A C13 H13B 107.9 . . ?
N1 C14 C8 111.35(18) . 2_656 ?
N1 C14 H14A 109.4 . . ?
N1 C14 H14B 109.4 . . ?
C8 C14 H14A 109.4 2_656 . ?
C8 C14 H14B 109.4 2_656 . ?
H14A C14 H14B 108.0 . . ?
O4 S1 C15 108.9(4) . . ?
O4 S1 C16 104.4(5) . . ?
C15 S1 C16 96.5(2) . . ?
O5 S2 C18 110.6(14) . . ?
O5 S2 C20 109(2) . . ?
C18 S2 C20 100(2) . . ?
O6 S3 C17 105(2) . . ?
O6 S3 C19 100.2(11) . . ?
C19 S3 C17 96(2) . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
S3 C17 H17A 109.5 . . ?
S3 C17 H17B 109.5 . . ?
S3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
S2 C18 H18A 109.5 . . ?
S2 C18 H18B 109.5 . . ?
S2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
S3 C19 H19A 109.5 . . ?
S3 C19 H19B 109.5 . . ?
S3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
S2 C20 H20A 109.5 . . ?
S2 C20 H20B 109.5 . . ?
S2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TB-3
_database_code_depnum_ccdc_archive 'CCDC 1564000'
_audit_update_record             
;
2017-07-23 deposited with the CCDC.
2017-08-14 downloaded from the CCDC.
;
_audit_creation_date             2017-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled Mar 28 2017 19:26:29 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
'N-Phenyl-1,8-naphthalimide Derived Trogers base'
_chemical_formula_moiety         'C39 H24 N4 O4, C H2 Cl2'
_chemical_formula_sum            'C40 H26 Cl2 N4 O4'
_chemical_formula_weight         697.55
_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'
Cl Cl 0.1484 0.1585 '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'

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

_cell_length_a                   10.406(2)
_cell_length_b                   11.383(3)
_cell_length_c                   13.621(3)
_cell_angle_alpha                83.448(9)
_cell_angle_beta                 87.0820(10)
_cell_angle_gamma                78.674(10)
_cell_volume                     1571.0(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3899
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.5
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   CrystalClear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12875
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.497
_diffrn_reflns_theta_min         2.439
_diffrn_ambient_temperature      100.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5104
_reflns_number_total             5827
_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       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         5827
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.048
_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)+(0.0940P)²+1.6293P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1644
_refine_ls_wR_factor_ref         0.1702
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C21(H21A,H21B), C40(H40A,H40B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C11(H11), C15(H15), C10(H10),
 C23(H23), C27(H27), C28(H28), C29(H29), C35(H35), C36(H36), C37(H37), C38(H38),
  C39(H39)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.03431(8) 0.83640(7) 0.02512(7) 0.0434(2) Uani 1 1 d . . . . .
Cl2 Cl -0.16088(8) 0.76871(8) -0.09290(8) 0.0513(3) Uani 1 1 d . . . . .
O1 O 1.08275(18) 0.87501(18) 0.55285(14) 0.0294(4) Uani 1 1 d . . . . .
N1 N 1.1536(2) 0.76938(19) 0.42147(15) 0.0193(4) Uani 1 1 d . . . . .
C1 C 1.2471(3) 0.9169(2) 0.31068(19) 0.0241(6) Uani 1 1 d . . . . .
H1 H 1.1744 0.9248 0.2693 0.029 Uiso 1 1 calc R . . . .
O2 O 1.24227(16) 0.64087(16) 0.30854(13) 0.0233(4) Uani 1 1 d . . . . .
N2 N 0.67756(19) 0.48779(18) 0.38564(15) 0.0175(4) Uani 1 1 d . . . . .
C2 C 1.3447(3) 0.9840(2) 0.2849(2) 0.0271(6) Uani 1 1 d . . . . .
H2 H 1.3390 1.0374 0.2257 0.032 Uiso 1 1 calc R . . . .
N3 N 0.74053(19) 0.40553(18) 0.22940(15) 0.0168(4) Uani 1 1 d . . . . .
O3 O 0.33022(17) 0.88058(16) 0.06399(13) 0.0235(4) Uani 1 1 d . . . . .
C3 C 1.4501(3) 0.9723(2) 0.3458(2) 0.0265(6) Uani 1 1 d . . . . .
H3 H 1.5159 1.0189 0.3289 0.032 Uiso 1 1 calc R . . . .
O4 O 0.50701(16) 0.75590(16) -0.22875(12) 0.0207(4) Uani 1 1 d . . . . .
N4 N 0.41843(19) 0.81864(17) -0.08251(14) 0.0161(4) Uani 1 1 d . . . . .
C4 C 1.4600(3) 0.8935(3) 0.4308(2) 0.0285(6) Uani 1 1 d . . . . .
H4 H 1.5333 0.8850 0.4715 0.034 Uiso 1 1 calc R . . . .
C5 C 1.3628(3) 0.8258(3) 0.4575(2) 0.0273(6) Uani 1 1 d . . . . .
H5 H 1.3695 0.7718 0.5163 0.033 Uiso 1 1 calc R . . . .
C6 C 1.2564(2) 0.8384(2) 0.39710(18) 0.0198(5) Uani 1 1 d . . . . .
C7 C 1.0636(2) 0.8019(2) 0.49955(19) 0.0210(5) Uani 1 1 d . . . . .
C8 C 0.9475(2) 0.7437(2) 0.51109(18) 0.0187(5) Uani 1 1 d . . . . .
C9 C 0.8527(2) 0.7759(2) 0.58270(18) 0.0219(5) Uani 1 1 d . . . . .
H9 H 0.8630 0.8339 0.6251 0.026 Uiso 1 1 calc R . . . .
C11 C 0.7221(2) 0.6422(2) 0.52981(18) 0.0199(5) Uani 1 1 d . . . . .
H11 H 0.6456 0.6079 0.5375 0.024 Uiso 1 1 calc R . . . .
C12 C 0.8159(2) 0.6095(2) 0.45320(17) 0.0171(5) Uani 1 1 d . . . . .
C13 C 0.7986(2) 0.5299(2) 0.38285(17) 0.0164(5) Uani 1 1 d . . . . .
C14 C 0.8975(2) 0.4949(2) 0.31405(17) 0.0165(5) Uani 1 1 d . . . . .
C15 C 1.0151(2) 0.5390(2) 0.31303(17) 0.0170(5) Uani 1 1 d . . . . .
H15 H 1.0840 0.5120 0.2676 0.020 Uiso 1 1 calc R . . . .
C16 C 1.0323(2) 0.6201(2) 0.37628(17) 0.0166(5) Uani 1 1 d . . . . .
C18 C 1.1516(2) 0.6735(2) 0.36487(17) 0.0178(5) Uani 1 1 d . . . . .
C17 C 0.9321(2) 0.6575(2) 0.44680(17) 0.0165(5) Uani 1 1 d . . . . .
C10 C 0.7409(2) 0.7231(2) 0.59306(18) 0.0228(5) Uani 1 1 d . . . . .
H10 H 0.6777 0.7434 0.6442 0.027 Uiso 1 1 calc R . . . .
C19 C 0.8794(2) 0.4156(2) 0.23542(18) 0.0177(5) Uani 1 1 d . . . . .
H19A H 0.9103 0.4500 0.1705 0.021 Uiso 1 1 calc R . . . .
H19B H 0.9334 0.3343 0.2509 0.021 Uiso 1 1 calc R . . . .
C21 C 0.5687(2) 0.5810(2) 0.34204(17) 0.0175(5) Uani 1 1 d . . . . .
H21A H 0.5733 0.6598 0.3643 0.021 Uiso 1 1 calc R . . . .
H21B H 0.4839 0.5601 0.3662 0.021 Uiso 1 1 calc R . . . .
C22 C 0.5746(2) 0.5917(2) 0.22966(17) 0.0156(5) Uani 1 1 d . . . . .
C23 C 0.4919(2) 0.6894(2) 0.17649(17) 0.0159(5) Uani 1 1 d . . . . .
H23 H 0.4322 0.7452 0.2116 0.019 Uiso 1 1 calc R . . . .
C24 C 0.4967(2) 0.7047(2) 0.07472(17) 0.0156(5) Uani 1 1 d . . . . .
C25 C 0.5840(2) 0.6208(2) 0.02131(17) 0.0150(5) Uani 1 1 d . . . . .
C26 C 0.5866(2) 0.6333(2) -0.08362(17) 0.0157(5) Uani 1 1 d . . . . .
C27 C 0.6665(2) 0.5483(2) -0.13507(18) 0.0176(5) Uani 1 1 d . . . . .
H27 H 0.6676 0.5571 -0.2053 0.021 Uiso 1 1 calc R . . . .
C28 C 0.7465(2) 0.4484(2) -0.08388(18) 0.0187(5) Uani 1 1 d . . . . .
H28 H 0.8002 0.3894 -0.1197 0.022 Uiso 1 1 calc R . . . .
C29 C 0.7474(2) 0.4357(2) 0.01770(18) 0.0171(5) Uani 1 1 d . . . . .
H29 H 0.8028 0.3684 0.0514 0.021 Uiso 1 1 calc R . . . .
C30 C 0.6665(2) 0.5216(2) 0.07278(17) 0.0154(5) Uani 1 1 d . . . . .
C31 C 0.6606(2) 0.5092(2) 0.17875(17) 0.0152(5) Uani 1 1 d . . . . .
C32 C 0.4083(2) 0.8074(2) 0.02191(18) 0.0166(5) Uani 1 1 d . . . . .
C33 C 0.5037(2) 0.7377(2) -0.13863(18) 0.0160(5) Uani 1 1 d . . . . .
C34 C 0.3347(2) 0.9205(2) -0.13642(17) 0.0168(5) Uani 1 1 d . . . . .
C35 C 0.2432(2) 0.8994(2) -0.19952(18) 0.0209(5) Uani 1 1 d . . . . .
H35 H 0.2332 0.8194 -0.2056 0.025 Uiso 1 1 calc R . . . .
C36 C 0.1659(3) 0.9966(3) -0.2539(2) 0.0278(6) Uani 1 1 d . . . . .
H36 H 0.1048 0.9831 -0.2989 0.033 Uiso 1 1 calc R . . . .
C37 C 0.1787(3) 1.1137(2) -0.2418(2) 0.0291(6) Uani 1 1 d . . . . .
H37 H 0.1253 1.1802 -0.2780 0.035 Uiso 1 1 calc R . . . .
C38 C 0.2685(3) 1.1335(2) -0.1774(2) 0.0284(6) Uani 1 1 d . . . . .
H38 H 0.2757 1.2135 -0.1686 0.034 Uiso 1 1 calc R . . . .
C39 C 0.3486(2) 1.0368(2) -0.1255(2) 0.0233(5) Uani 1 1 d . . . . .
H39 H 0.4123 1.0503 -0.0827 0.028 Uiso 1 1 calc R . . . .
C40 C -0.0885(3) 0.8875(3) -0.0627(3) 0.0402(8) Uani 1 1 d . . . . .
H40A H -0.0497 0.9248 -0.1234 0.048 Uiso 1 1 calc R . . . .
H40B H -0.1570 0.9500 -0.0360 0.048 Uiso 1 1 calc R . . . .
C20 C 0.6901(2) 0.3821(2) 0.33085(18) 0.0192(5) Uani 1 1 d . . . . .
H20A H 0.7501 0.3135 0.3658 0.023 Uiso 1 1 calc R . . . .
H20B H 0.6032 0.3594 0.3290 0.023 Uiso 1 1 calc R . . . .


_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 C40 1.762(3) . ?
Cl2 C40 1.768(3) . ?
O1 C7 1.215(3) . ?
N1 C6 1.452(3) . ?
N1 C7 1.413(3) . ?
N1 C18 1.410(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.396(4) . ?
C1 C6 1.389(4) . ?
O2 C18 1.213(3) . ?
N2 C13 1.431(3) . ?
N2 C21 1.488(3) . ?
N2 C20 1.468(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
N3 C19 1.479(3) . ?
N3 C31 1.431(3) . ?
N3 C20 1.467(3) . ?
O3 C32 1.216(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(4) . ?
O4 C33 1.221(3) . ?
N4 C32 1.414(3) . ?
N4 C33 1.411(3) . ?
N4 C34 1.455(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(4) . ?
C7 C8 1.482(3) . ?
C8 C9 1.379(3) . ?
C8 C17 1.423(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.404(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.422(3) . ?
C11 C10 1.378(4) . ?
C12 C13 1.432(3) . ?
C12 C17 1.417(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.410(3) . ?
C14 C19 1.518(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.375(3) . ?
C16 C18 1.480(3) . ?
C16 C17 1.418(3) . ?
C10 H10 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.521(3) . ?
C22 C23 1.416(3) . ?
C22 C31 1.386(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.377(3) . ?
C24 C25 1.420(3) . ?
C24 C32 1.477(3) . ?
C25 C26 1.419(3) . ?
C25 C30 1.416(3) . ?
C26 C27 1.378(3) . ?
C26 C33 1.476(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.406(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.375(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.417(3) . ?
C30 C31 1.433(3) . ?
C34 C35 1.387(4) . ?
C34 C39 1.385(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.394(4) . ?
C36 H36 0.9500 . ?
C36 C37 1.395(4) . ?
C37 H37 0.9500 . ?
C37 C38 1.380(4) . ?
C38 H38 0.9500 . ?
C38 C39 1.388(4) . ?
C39 H39 0.9500 . ?
C40 H40A 0.9900 . ?
C40 H40B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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
C7 N1 C6 118.4(2) . . ?
C18 N1 C6 116.88(19) . . ?
C18 N1 C7 124.7(2) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.8(2) . . ?
C13 N2 C21 112.44(18) . . ?
C13 N2 C20 111.03(19) . . ?
C20 N2 C21 107.46(18) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C31 N3 C19 113.96(18) . . ?
C31 N3 C20 110.70(19) . . ?
C20 N3 C19 107.38(18) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C32 N4 C34 117.95(19) . . ?
C33 N4 C32 124.69(19) . . ?
C33 N4 C34 117.36(19) . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 N1 118.4(2) . . ?
C5 C6 N1 121.3(2) . . ?
C5 C6 C1 120.3(2) . . ?
O1 C7 N1 120.2(2) . . ?
O1 C7 C8 123.1(2) . . ?
N1 C7 C8 116.7(2) . . ?
C9 C8 C7 119.6(2) . . ?
C9 C8 C17 120.2(2) . . ?
C17 C8 C7 120.2(2) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(2) . . ?
C11 C12 C13 123.1(2) . . ?
C17 C12 C11 118.3(2) . . ?
C17 C12 C13 118.6(2) . . ?
N2 C13 C12 118.4(2) . . ?
C14 C13 N2 121.2(2) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 C19 121.6(2) . . ?
C15 C14 C19 118.8(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 C14 121.5(2) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C18 119.2(2) . . ?
C15 C16 C17 119.7(2) . . ?
C17 C16 C18 120.9(2) . . ?
N1 C18 C16 116.2(2) . . ?
O2 C18 N1 120.6(2) . . ?
O2 C18 C16 123.2(2) . . ?
C12 C17 C8 119.8(2) . . ?
C12 C17 C16 120.0(2) . . ?
C16 C17 C8 120.2(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
N3 C19 C14 111.58(19) . . ?
N3 C19 H19A 109.3 . . ?
N3 C19 H19B 109.3 . . ?
C14 C19 H19A 109.3 . . ?
C14 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
N2 C21 H21A 109.2 . . ?
N2 C21 H21B 109.2 . . ?
N2 C21 C22 112.00(19) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C23 C22 C21 119.0(2) . . ?
C31 C22 C21 121.3(2) . . ?
C31 C22 C23 119.7(2) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.0(2) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 C25 120.1(2) . . ?
C23 C24 C32 119.4(2) . . ?
C25 C24 C32 120.5(2) . . ?
C26 C25 C24 120.6(2) . . ?
C30 C25 C24 120.0(2) . . ?
C30 C25 C26 119.4(2) . . ?
C25 C26 C33 120.2(2) . . ?
C27 C26 C25 120.4(2) . . ?
C27 C26 C33 119.4(2) . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.2(2) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(2) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 119.6 . . ?
C28 C29 C30 120.8(2) . . ?
C30 C29 H29 119.6 . . ?
C25 C30 C29 118.8(2) . . ?
C25 C30 C31 118.6(2) . . ?
C29 C30 C31 122.5(2) . . ?
N3 C31 C30 117.8(2) . . ?
C22 C31 N3 121.5(2) . . ?
C22 C31 C30 120.6(2) . . ?
O3 C32 N4 120.1(2) . . ?
O3 C32 C24 123.2(2) . . ?
N4 C32 C24 116.8(2) . . ?
O4 C33 N4 120.0(2) . . ?
O4 C33 C26 122.9(2) . . ?
N4 C33 C26 117.1(2) . . ?
C35 C34 N4 119.3(2) . . ?
C39 C34 N4 119.8(2) . . ?
C39 C34 C35 120.9(2) . . ?
C34 C35 H35 120.2 . . ?
C34 C35 C36 119.5(2) . . ?
C36 C35 H35 120.2 . . ?
C35 C36 H36 120.2 . . ?
C35 C36 C37 119.5(2) . . ?
C37 C36 H36 120.2 . . ?
C36 C37 H37 119.8 . . ?
C38 C37 C36 120.3(2) . . ?
C38 C37 H37 119.8 . . ?
C37 C38 H38 119.9 . . ?
C37 C38 C39 120.3(3) . . ?
C39 C38 H38 119.9 . . ?
C34 C39 C38 119.5(2) . . ?
C34 C39 H39 120.3 . . ?
C38 C39 H39 120.3 . . ?
Cl1 C40 Cl2 111.68(18) . . ?
Cl1 C40 H40A 109.3 . . ?
Cl1 C40 H40B 109.3 . . ?
Cl2 C40 H40A 109.3 . . ?
Cl2 C40 H40B 109.3 . . ?
H40A C40 H40B 107.9 . . ?
N2 C20 H20A 109.3 . . ?
N2 C20 H20B 109.3 . . ?
N3 C20 N2 111.80(19) . . ?
N3 C20 H20A 109.3 . . ?
N3 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?

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
O1 C7 C8 C9 2.7(4) . . . . ?
O1 C7 C8 C17 -179.2(2) . . . . ?
N1 C7 C8 C9 -176.8(2) . . . . ?
N1 C7 C8 C17 1.4(3) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
N2 C13 C14 C15 179.5(2) . . . . ?
N2 C13 C14 C19 3.2(3) . . . . ?
N2 C21 C22 C23 -169.5(2) . . . . ?
N2 C21 C22 C31 9.4(3) . . . . ?
C2 C1 C6 N1 -179.6(2) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 0.4(4) . . . . ?
N4 C34 C35 C36 -177.8(2) . . . . ?
N4 C34 C39 C38 179.8(2) . . . . ?
C4 C5 C6 N1 179.6(2) . . . . ?
C4 C5 C6 C1 0.4(4) . . . . ?
C6 N1 C7 O1 -9.6(4) . . . . ?
C6 N1 C7 C8 169.9(2) . . . . ?
C6 N1 C18 O2 10.0(3) . . . . ?
C6 N1 C18 C16 -168.0(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C7 N1 C6 C1 -107.1(3) . . . . ?
C7 N1 C6 C5 73.7(3) . . . . ?
C7 N1 C18 O2 -169.8(2) . . . . ?
C7 N1 C18 C16 12.2(3) . . . . ?
C7 C8 C9 C10 178.7(2) . . . . ?
C7 C8 C17 C12 -175.0(2) . . . . ?
C7 C8 C17 C16 4.8(3) . . . . ?
C8 C9 C10 C11 -2.4(4) . . . . ?
C9 C8 C17 C12 3.2(3) . . . . ?
C9 C8 C17 C16 -177.0(2) . . . . ?
C11 C12 C13 N2 4.3(3) . . . . ?
C11 C12 C13 C14 -175.5(2) . . . . ?
C11 C12 C17 C8 -5.0(3) . . . . ?
C11 C12 C17 C16 175.2(2) . . . . ?
C12 C11 C10 C9 0.6(4) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C12 C13 C14 C19 -176.9(2) . . . . ?
C13 N2 C21 C22 78.9(2) . . . . ?
C13 N2 C20 N3 -54.0(3) . . . . ?
C13 C12 C17 C8 175.4(2) . . . . ?
C13 C12 C17 C16 -4.4(3) . . . . ?
C13 C14 C15 C16 -2.7(3) . . . . ?
C13 C14 C19 N3 12.3(3) . . . . ?
C14 C15 C16 C18 -173.4(2) . . . . ?
C14 C15 C16 C17 2.3(3) . . . . ?
C15 C14 C19 N3 -164.1(2) . . . . ?
C15 C16 C18 N1 170.4(2) . . . . ?
C15 C16 C18 O2 -7.5(4) . . . . ?
C15 C16 C17 C8 -178.5(2) . . . . ?
C15 C16 C17 C12 1.3(3) . . . . ?
C18 N1 C6 C1 73.1(3) . . . . ?
C18 N1 C6 C5 -106.0(3) . . . . ?
C18 N1 C7 O1 170.1(2) . . . . ?
C18 N1 C7 C8 -10.4(3) . . . . ?
C18 C16 C17 C8 -2.9(3) . . . . ?
C18 C16 C17 C12 176.9(2) . . . . ?
C17 C8 C9 C10 0.5(4) . . . . ?
C17 C12 C13 N2 -176.1(2) . . . . ?
C17 C12 C13 C14 4.1(3) . . . . ?
C17 C16 C18 N1 -5.2(3) . . . . ?
C17 C16 C18 O2 176.8(2) . . . . ?
C10 C11 C12 C13 -177.3(2) . . . . ?
C10 C11 C12 C17 3.1(3) . . . . ?
C19 N3 C31 C22 -103.8(2) . . . . ?
C19 N3 C31 C30 79.7(3) . . . . ?
C19 N3 C20 N2 69.7(2) . . . . ?
C19 C14 C15 C16 173.8(2) . . . . ?
C21 N2 C13 C12 76.5(3) . . . . ?
C21 N2 C13 C14 -103.7(2) . . . . ?
C21 N2 C20 N3 69.4(2) . . . . ?
C21 C22 C23 C24 178.0(2) . . . . ?
C21 C22 C31 N3 4.7(3) . . . . ?
C21 C22 C31 C30 -179.0(2) . . . . ?
C22 C23 C24 C25 1.1(3) . . . . ?
C22 C23 C24 C32 179.6(2) . . . . ?
C23 C22 C31 N3 -176.4(2) . . . . ?
C23 C22 C31 C30 -0.1(3) . . . . ?
C23 C24 C25 C26 177.8(2) . . . . ?
C23 C24 C25 C30 -0.4(3) . . . . ?
C23 C24 C32 O3 0.1(4) . . . . ?
C23 C24 C32 N4 179.7(2) . . . . ?
C24 C25 C26 C27 -176.7(2) . . . . ?
C24 C25 C26 C33 3.4(3) . . . . ?
C24 C25 C30 C29 176.6(2) . . . . ?
C24 C25 C30 C31 -0.6(3) . . . . ?
C25 C24 C32 O3 178.7(2) . . . . ?
C25 C24 C32 N4 -1.8(3) . . . . ?
C25 C26 C27 C28 -0.2(3) . . . . ?
C25 C26 C33 O4 176.3(2) . . . . ?
C25 C26 C33 N4 -3.4(3) . . . . ?
C25 C30 C31 N3 177.30(19) . . . . ?
C25 C30 C31 C22 0.8(3) . . . . ?
C26 C25 C30 C29 -1.6(3) . . . . ?
C26 C25 C30 C31 -178.8(2) . . . . ?
C26 C27 C28 C29 -1.1(4) . . . . ?
C27 C26 C33 O4 -3.7(3) . . . . ?
C27 C26 C33 N4 176.6(2) . . . . ?
C27 C28 C29 C30 1.0(4) . . . . ?
C28 C29 C30 C25 0.4(3) . . . . ?
C28 C29 C30 C31 177.4(2) . . . . ?
C29 C30 C31 N3 0.2(3) . . . . ?
C29 C30 C31 C22 -176.3(2) . . . . ?
C30 C25 C26 C27 1.5(3) . . . . ?
C30 C25 C26 C33 -178.5(2) . . . . ?
C31 N3 C19 C14 77.2(2) . . . . ?
C31 N3 C20 N2 -55.2(2) . . . . ?
C31 C22 C23 C24 -0.9(3) . . . . ?
C32 N4 C33 O4 -178.9(2) . . . . ?
C32 N4 C33 C26 0.8(3) . . . . ?
C32 N4 C34 C35 -117.8(2) . . . . ?
C32 N4 C34 C39 63.3(3) . . . . ?
C32 C24 C25 C26 -0.7(3) . . . . ?
C32 C24 C25 C30 -178.9(2) . . . . ?
C33 N4 C32 O3 -178.7(2) . . . . ?
C33 N4 C32 C24 1.7(3) . . . . ?
C33 N4 C34 C35 61.9(3) . . . . ?
C33 N4 C34 C39 -117.0(2) . . . . ?
C33 C26 C27 C28 179.8(2) . . . . ?
C34 N4 C32 O3 1.0(3) . . . . ?
C34 N4 C32 C24 -178.60(19) . . . . ?
C34 N4 C33 O4 1.4(3) . . . . ?
C34 N4 C33 C26 -178.87(19) . . . . ?
C34 C35 C36 C37 -2.0(4) . . . . ?
C35 C34 C39 C38 0.9(4) . . . . ?
C35 C36 C37 C38 0.9(4) . . . . ?
C36 C37 C38 C39 1.1(4) . . . . ?
C37 C38 C39 C34 -2.0(4) . . . . ?
C39 C34 C35 C36 1.2(4) . . . . ?
C20 N2 C13 C12 -163.1(2) . . . . ?
C20 N2 C13 C14 16.8(3) . . . . ?
C20 N2 C21 C22 -43.6(2) . . . . ?
C20 N3 C19 C14 -45.8(2) . . . . ?
C20 N3 C31 C22 17.3(3) . . . . ?
C20 N3 C31 C30 -159.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
