# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_mo_b0419_0m
_database_code_depnum_ccdc_archive 'CCDC 2097365'
loop_
_audit_author_name
_audit_author_address
'Christopher Golz'
;Georg August University Goettingen
Germany
;
_audit_update_record             
;
2021-07-19 deposited with the CCDC.	2022-09-08 downloaded from the CCDC.
;
_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
4''-((E)-4-fluorobenzylidene)-1'-(4-fluorophenyl)-5-nitro-1'',4'',5',6',7',7a'-hexahydro-1'H,3''H-dispiro[indoline-3,3'-pyrrolizine-2',2''-naphthalene]-2,3''-dione
_chemical_formula_moiety         'C36 H27 F2 N3 O4, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C38 H31 F2 N3 O5'
_chemical_formula_weight         647.66
_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 0.0033 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'
F F 0.0171 0.0103 '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                   8.244(4)
_cell_length_b                   12.956(6)
_cell_length_c                   15.359(8)
_cell_angle_alpha                75.195(19)
_cell_angle_beta                 80.54(2)
_cell_angle_gamma                77.813(17)
_cell_volume                     1539.6(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9146
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.72
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1392 before and 0.0436 after correction.
The Ratio of minimum to maximum transmission is 0.9060.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.082
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20681
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.616
_diffrn_reflns_theta_min         2.778
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 10.4167
_diffrn_detector_type            'CMOS PHOTON100 area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6154
_reflns_number_total             8000
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0081(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         8000
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0470
_refine_ls_restrained_S_all      1.037
_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)+(0.0578P)²+0.6962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1271
_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. Restrained distances
 O6-C37
 1.32 with sigma of 0.02
 O6-C39
 1.46 with sigma of 0.02
 O5-C37
 1.22 with sigma of 0.02
 C38-C37
 1.49 with sigma of 0.02
 C39-C40
 1.5 with sigma of 0.02
 O6-C38
 2.35 with sigma of 0.04
 O5-C38
 2.4 with sigma of 0.04
 O6-O5
 2.24 with sigma of 0.04
 O6-C40
 2.38 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C37, C38, O5, O6, C39, C40
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O5(0.5) O6(0.5) C37(0.5) C38(0.5) H38A(0.5) H38B(0.5) H38C(0.5)
 C39(0.5) H39A(0.5) H39B(0.5) C40(0.5) H40A(0.5) H40B(0.5) H40C(0.5)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C25(H25A,H25B), C39(H39A,H39B)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C8(H8), C16(H16), C17(H17), C19(H19), C20(H20),
 C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C35(H35),
  C36(H36)
5.d Idealised Me refined as rotating group:
 C38(H38A,H38B,H38C), C40(H40A,H40B,H40C)
;
_atom_sites_solution_hydrogens   geom
_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
F1 F -0.02155(12) 0.92537(7) 0.65544(7) 0.0286(2) Uani 1 1 d . . . . .
F2 F 0.37362(12) 0.00618(8) 0.36430(6) 0.0288(2) Uani 1 1 d . . . . .
O1 O 0.71564(13) 0.49361(9) 0.78904(7) 0.0228(2) Uani 1 1 d . . . . .
O2 O 0.15239(12) 0.34539(9) 0.76709(7) 0.0213(2) Uani 1 1 d . . . . .
O3 O 0.33304(18) 0.00664(11) 0.80062(11) 0.0446(4) Uani 1 1 d . . . . .
O4 O 0.5477(2) -0.11927(10) 0.83155(9) 0.0430(4) Uani 1 1 d . . . . .
N1 N 0.81570(15) 0.31282(11) 0.79400(9) 0.0210(3) Uani 1 1 d . . . . .
H1 H 0.923231 0.314873 0.786245 0.025 Uiso 1 1 calc R U . . .
N2 N 0.46491(14) 0.37703(9) 0.91391(8) 0.0160(2) Uani 1 1 d . . . . .
N3 N 0.4781(2) -0.02390(11) 0.81808(9) 0.0307(3) Uani 1 1 d . . . . .
C1 C 0.69275(17) 0.40173(12) 0.79782(9) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.52167(16) 0.36098(11) 0.82117(9) 0.0147(3) Uani 1 1 d . . . . .
C3 C 0.57593(17) 0.24219(11) 0.81854(9) 0.0159(3) Uani 1 1 d . . . . .
C4 C 0.75151(17) 0.21933(12) 0.80372(9) 0.0188(3) Uani 1 1 d . . . . .
C5 C 0.83836(19) 0.11602(13) 0.80004(10) 0.0248(3) Uani 1 1 d . . . . .
H5 H 0.957047 0.101396 0.792137 0.030 Uiso 1 1 calc R U . . .
C6 C 0.7474(2) 0.03484(13) 0.80821(10) 0.0269(3) Uani 1 1 d . . . . .
H6 H 0.803083 -0.036757 0.806188 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5742(2) 0.05908(12) 0.81938(10) 0.0224(3) Uani 1 1 d . . . . .
C8 C 0.48568(18) 0.16095(12) 0.82635(9) 0.0180(3) Uani 1 1 d . . . . .
H8 H 0.367051 0.174428 0.836170 0.022 Uiso 1 1 calc R U . . .
C9 C 0.38424(16) 0.43527(11) 0.75772(9) 0.0140(3) Uani 1 1 d . . . . .
C10 C 0.26739(16) 0.50148(11) 0.82288(9) 0.0148(3) Uani 1 1 d . . . . .
H10 H 0.171448 0.462418 0.848114 0.018 Uiso 1 1 calc R U . . .
C11 C 0.36783(17) 0.48825(11) 0.90280(9) 0.0168(3) Uani 1 1 d . . . . .
H11 H 0.443609 0.542816 0.888299 0.020 Uiso 1 1 calc R U . . .
C12 C 0.25952(19) 0.49068(13) 0.99419(10) 0.0222(3) Uani 1 1 d . . . . .
H12A H 0.142257 0.524253 0.984923 0.027 Uiso 1 1 calc R U . . .
H12B H 0.302856 0.532017 1.028550 0.027 Uiso 1 1 calc R U . . .
C13 C 0.2720(2) 0.37010(13) 1.04488(10) 0.0248(3) Uani 1 1 d . . . . .
H13A H 0.342886 0.352948 1.094651 0.030 Uiso 1 1 calc R U . . .
H13B H 0.159934 0.353080 1.070583 0.030 Uiso 1 1 calc R U . . .
C14 C 0.35128(18) 0.30614(12) 0.97271(10) 0.0197(3) Uani 1 1 d . . . . .
H14A H 0.413935 0.234188 1.000051 0.024 Uiso 1 1 calc R U . . .
H14B H 0.265897 0.296328 0.938553 0.024 Uiso 1 1 calc R U . . .
C15 C 0.19256(17) 0.61626(11) 0.77945(9) 0.0159(3) Uani 1 1 d . . . . .
C16 C 0.26585(19) 0.70510(12) 0.77510(11) 0.0244(3) Uani 1 1 d . . . . .
H16 H 0.367315 0.694151 0.800600 0.029 Uiso 1 1 calc R U . . .
C17 C 0.1934(2) 0.80960(13) 0.73412(12) 0.0254(3) Uani 1 1 d . . . . .
H17 H 0.243321 0.870084 0.731899 0.030 Uiso 1 1 calc R U . . .
C18 C 0.04783(18) 0.82302(12) 0.69698(10) 0.0207(3) Uani 1 1 d . . . . .
C19 C -0.03046(19) 0.73765(13) 0.70078(12) 0.0264(3) Uani 1 1 d . . . . .
H19 H -0.131889 0.749431 0.675062 0.032 Uiso 1 1 calc R U . . .
C20 C 0.04226(18) 0.63423(13) 0.74298(11) 0.0222(3) Uani 1 1 d . . . . .
H20 H -0.011125 0.574657 0.747131 0.027 Uiso 1 1 calc R U . . .
C21 C 0.28923(16) 0.36303(11) 0.72770(9) 0.0153(3) Uani 1 1 d . . . . .
C22 C 0.36933(17) 0.31484(11) 0.64816(9) 0.0159(3) Uani 1 1 d . . . . .
C23 C 0.53940(17) 0.33633(11) 0.60892(9) 0.0163(3) Uani 1 1 d . . . . .
C24 C 0.58309(17) 0.43336(12) 0.61557(9) 0.0172(3) Uani 1 1 d . . . . .
C25 C 0.45988(17) 0.50515(11) 0.66861(9) 0.0168(3) Uani 1 1 d . . . . .
H25A H 0.369496 0.546475 0.631618 0.020 Uiso 1 1 calc R U . . .
H25B H 0.516950 0.557693 0.683024 0.020 Uiso 1 1 calc R U . . .
C26 C 0.66085(18) 0.26135(12) 0.57161(10) 0.0202(3) Uani 1 1 d . . . . .
H26 H 0.635109 0.193629 0.570501 0.024 Uiso 1 1 calc R U . . .
C27 C 0.81829(18) 0.28481(13) 0.53626(11) 0.0243(3) Uani 1 1 d . . . . .
H27 H 0.899295 0.233451 0.510705 0.029 Uiso 1 1 calc R U . . .
C28 C 0.85802(19) 0.38344(14) 0.53811(11) 0.0258(3) Uani 1 1 d . . . . .
H28 H 0.964386 0.400641 0.511704 0.031 Uiso 1 1 calc R U . . .
C29 C 0.74135(18) 0.45674(13) 0.57879(10) 0.0218(3) Uani 1 1 d . . . . .
H29 H 0.769575 0.523143 0.581556 0.026 Uiso 1 1 calc R U . . .
C30 C 0.27876(17) 0.25221(11) 0.62479(9) 0.0171(3) Uani 1 1 d . . . . .
H30 H 0.176842 0.245207 0.663076 0.020 Uiso 1 1 calc R U . . .
C31 C 0.30588(17) 0.19302(11) 0.55250(9) 0.0168(3) Uani 1 1 d . . . . .
C32 C 0.39458(18) 0.22465(12) 0.46663(10) 0.0200(3) Uani 1 1 d . . . . .
H32 H 0.440716 0.289090 0.452134 0.024 Uiso 1 1 calc R U . . .
C33 C 0.41536(19) 0.16253(13) 0.40278(10) 0.0221(3) Uani 1 1 d . . . . .
H33 H 0.474749 0.183990 0.344586 0.027 Uiso 1 1 calc R U . . .
C34 C 0.34779(18) 0.06875(12) 0.42570(10) 0.0206(3) Uani 1 1 d . . . . .
C35 C 0.25439(19) 0.03645(12) 0.50752(10) 0.0207(3) Uani 1 1 d . . . . .
H35 H 0.206535 -0.027192 0.520581 0.025 Uiso 1 1 calc R U . . .
C36 C 0.23255(18) 0.10019(12) 0.57038(10) 0.0190(3) Uani 1 1 d . . . . .
H36 H 0.166453 0.080453 0.626750 0.023 Uiso 1 1 calc R U . . .
O5 O 0.1195(5) 0.1300(3) 0.9358(3) 0.0740(12) Uani 0.5 1 d D . P A -1
O6 O -0.0330(4) 0.0033(5) 1.0080(4) 0.0389(9) Uani 0.5 1 d D . P A -1
C37 C 0.0006(5) 0.1047(4) 0.9864(3) 0.0425(9) Uani 0.5 1 d D . P A -1
C38 C -0.1315(7) 0.1810(4) 1.0272(3) 0.0509(11) Uani 0.5 1 d D . P A -1
H38A H -0.229894 0.198138 0.994520 0.076 Uiso 0.5 1 calc R U P A -1
H38B H -0.089862 0.247840 1.022938 0.076 Uiso 0.5 1 calc R U P A -1
H38C H -0.162008 0.147615 1.091030 0.076 Uiso 0.5 1 calc R U P A -1
C39 C 0.0880(5) -0.0782(4) 0.9709(3) 0.0416(9) Uani 0.5 1 d D . P A -1
H39A H 0.192895 -0.093736 0.999000 0.050 Uiso 0.5 1 calc R U P A -1
H39B H 0.113766 -0.052062 0.904598 0.050 Uiso 0.5 1 calc R U P A -1
C40 C 0.0127(7) -0.1787(4) 0.9911(3) 0.0464(10) Uani 0.5 1 d D . P A -1
H40A H -0.092888 -0.161859 0.964717 0.070 Uiso 0.5 1 calc R U P A -1
H40B H -0.008285 -0.205467 1.056931 0.070 Uiso 0.5 1 calc R U P A -1
H40C H 0.090051 -0.234497 0.964940 0.070 Uiso 0.5 1 calc R U P A -1


_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
F1 C18 1.3637(17) . ?
F2 C34 1.3578(17) . ?
O1 C1 1.2146(19) . ?
O2 C21 1.2266(17) . ?
O3 N3 1.229(2) . ?
O4 N3 1.2278(19) . ?
N1 H1 0.8800 . ?
N1 C1 1.371(2) . ?
N1 C4 1.386(2) . ?
N2 C2 1.4772(19) . ?
N2 C11 1.4758(19) . ?
N2 C14 1.4826(18) . ?
N3 C7 1.469(2) . ?
C1 C2 1.5645(19) . ?
C2 C3 1.518(2) . ?
C2 C9 1.6072(19) . ?
C3 C4 1.407(2) . ?
C3 C8 1.383(2) . ?
C4 C5 1.388(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.385(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.387(2) . ?
C7 C8 1.388(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.5615(19) . ?
C9 C21 1.5332(19) . ?
C9 C25 1.551(2) . ?
C10 H10 1.0000 . ?
C10 C11 1.545(2) . ?
C10 C15 1.509(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.539(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.547(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.531(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.391(2) . ?
C15 C20 1.394(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.372(2) . ?
C18 C19 1.378(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.506(2) . ?
C22 C23 1.486(2) . ?
C22 C30 1.356(2) . ?
C23 C24 1.410(2) . ?
C23 C26 1.400(2) . ?
C24 C25 1.509(2) . ?
C24 C29 1.397(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26 0.9500 . ?
C26 C27 1.386(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.393(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.392(2) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C30 C31 1.467(2) . ?
C31 C32 1.405(2) . ?
C31 C36 1.404(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.389(2) . ?
C33 H33 0.9500 . ?
C33 C34 1.383(2) . ?
C34 C35 1.377(2) . ?
C35 H35 0.9500 . ?
C35 C36 1.391(2) . ?
C36 H36 0.9500 . ?
O5 C37 1.195(5) . ?
O6 C37 1.346(7) . ?
O6 C39 1.453(7) . ?
C37 C38 1.481(6) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C39 C40 1.499(6) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 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
C1 N1 H1 123.8 . . ?
C1 N1 C4 112.38(12) . . ?
C4 N1 H1 123.8 . . ?
C2 N2 C14 117.41(11) . . ?
C11 N2 C2 105.83(11) . . ?
C11 N2 C14 105.30(11) . . ?
O3 N3 C7 117.84(14) . . ?
O4 N3 O3 123.41(15) . . ?
O4 N3 C7 118.71(16) . . ?
O1 C1 N1 125.44(13) . . ?
O1 C1 C2 127.19(13) . . ?
N1 C1 C2 107.27(12) . . ?
N2 C2 C1 103.01(10) . . ?
N2 C2 C3 112.81(11) . . ?
N2 C2 C9 107.01(11) . . ?
C1 C2 C9 112.42(11) . . ?
C3 C2 C1 101.55(11) . . ?
C3 C2 C9 118.93(11) . . ?
C4 C3 C2 108.57(12) . . ?
C8 C3 C2 131.88(13) . . ?
C8 C3 C4 119.53(13) . . ?
N1 C4 C3 109.89(13) . . ?
N1 C4 C5 128.16(14) . . ?
C5 C4 C3 121.95(14) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 C4 118.25(15) . . ?
C6 C5 H5 120.9 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.38(14) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 N3 119.23(14) . . ?
C6 C7 C8 123.03(14) . . ?
C8 C7 N3 117.62(15) . . ?
C3 C8 C7 117.77(14) . . ?
C3 C8 H8 121.1 . . ?
C7 C8 H8 121.1 . . ?
C10 C9 C2 102.45(11) . . ?
C21 C9 C2 109.73(11) . . ?
C21 C9 C10 110.99(11) . . ?
C21 C9 C25 105.32(11) . . ?
C25 C9 C2 113.69(11) . . ?
C25 C9 C10 114.75(11) . . ?
C9 C10 H10 106.3 . . ?
C11 C10 C9 105.27(11) . . ?
C11 C10 H10 106.3 . . ?
C15 C10 C9 115.82(12) . . ?
C15 C10 H10 106.3 . . ?
C15 C10 C11 115.99(11) . . ?
N2 C11 C10 104.31(11) . . ?
N2 C11 H11 110.9 . . ?
N2 C11 C12 105.31(12) . . ?
C10 C11 H11 110.9 . . ?
C12 C11 C10 114.22(12) . . ?
C12 C11 H11 110.9 . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
C11 C12 C13 104.65(12) . . ?
H12A C12 H12B 108.9 . . ?
C13 C12 H12A 110.8 . . ?
C13 C12 H12B 110.8 . . ?
C12 C13 H13A 110.8 . . ?
C12 C13 H13B 110.8 . . ?
H13A C13 H13B 108.8 . . ?
C14 C13 C12 104.87(12) . . ?
C14 C13 H13A 110.8 . . ?
C14 C13 H13B 110.8 . . ?
N2 C14 C13 102.16(12) . . ?
N2 C14 H14A 111.3 . . ?
N2 C14 H14B 111.3 . . ?
C13 C14 H14A 111.3 . . ?
C13 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
C16 C15 C10 122.95(13) . . ?
C16 C15 C20 118.51(14) . . ?
C20 C15 C10 118.54(12) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.23(14) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.9 . . ?
C18 C17 C16 118.20(14) . . ?
C18 C17 H17 120.9 . . ?
F1 C18 C17 118.12(14) . . ?
F1 C18 C19 119.29(14) . . ?
C17 C18 C19 122.59(14) . . ?
C18 C19 H19 120.8 . . ?
C18 C19 C20 118.44(14) . . ?
C20 C19 H19 120.8 . . ?
C15 C20 H20 119.5 . . ?
C19 C20 C15 121.00(14) . . ?
C19 C20 H20 119.5 . . ?
O2 C21 C9 121.01(12) . . ?
O2 C21 C22 121.22(12) . . ?
C22 C21 C9 117.77(11) . . ?
C23 C22 C21 116.68(12) . . ?
C30 C22 C21 114.88(12) . . ?
C30 C22 C23 128.35(13) . . ?
C24 C23 C22 118.13(12) . . ?
C26 C23 C22 122.83(13) . . ?
C26 C23 C24 118.89(13) . . ?
C23 C24 C25 118.18(12) . . ?
C29 C24 C23 119.74(13) . . ?
C29 C24 C25 121.94(13) . . ?
C9 C25 H25A 109.6 . . ?
C9 C25 H25B 109.6 . . ?
C24 C25 C9 110.05(12) . . ?
C24 C25 H25A 109.6 . . ?
C24 C25 H25B 109.6 . . ?
H25A C25 H25B 108.2 . . ?
C23 C26 H26 119.6 . . ?
C27 C26 C23 120.74(14) . . ?
C27 C26 H26 119.6 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.19(14) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.77(14) . . ?
C29 C28 H28 120.1 . . ?
C24 C29 H29 119.8 . . ?
C28 C29 C24 120.47(14) . . ?
C28 C29 H29 119.8 . . ?
C22 C30 H30 113.4 . . ?
C22 C30 C31 133.16(13) . . ?
C31 C30 H30 113.4 . . ?
C32 C31 C30 124.74(13) . . ?
C36 C31 C30 116.88(13) . . ?
C36 C31 C32 118.35(13) . . ?
C31 C32 H32 119.7 . . ?
C33 C32 C31 120.58(14) . . ?
C33 C32 H32 119.7 . . ?
C32 C33 H33 120.7 . . ?
C34 C33 C32 118.61(14) . . ?
C34 C33 H33 120.7 . . ?
F2 C34 C33 118.42(14) . . ?
F2 C34 C35 118.52(14) . . ?
C35 C34 C33 123.06(14) . . ?
C34 C35 H35 121.1 . . ?
C34 C35 C36 117.71(14) . . ?
C36 C35 H35 121.1 . . ?
C31 C36 H36 119.2 . . ?
C35 C36 C31 121.56(14) . . ?
C35 C36 H36 119.2 . . ?
C37 O6 C39 117.1(3) . . ?
O5 C37 O6 122.9(4) . . ?
O5 C37 C38 124.6(4) . . ?
O6 C37 C38 112.4(4) . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O6 C39 H39A 110.2 . . ?
O6 C39 H39B 110.2 . . ?
O6 C39 C40 107.6(4) . . ?
H39A C39 H39B 108.5 . . ?
C40 C39 H39A 110.2 . . ?
C40 C39 H39B 110.2 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.88 1.97 2.8429(19) 170.6 1_655

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
F1 C18 C19 C20 179.77(14) . . . . ?
F2 C34 C35 C36 178.52(12) . . . . ?
O1 C1 C2 N2 -65.27(17) . . . . ?
O1 C1 C2 C3 177.77(14) . . . . ?
O1 C1 C2 C9 49.57(19) . . . . ?
O2 C21 C22 C23 -176.59(13) . . . . ?
O2 C21 C22 C30 0.1(2) . . . . ?
O3 N3 C7 C6 -158.46(15) . . . . ?
O3 N3 C7 C8 17.7(2) . . . . ?
O4 N3 C7 C6 19.3(2) . . . . ?
O4 N3 C7 C8 -164.54(14) . . . . ?
N1 C1 C2 N2 111.30(12) . . . . ?
N1 C1 C2 C3 -5.67(13) . . . . ?
N1 C1 C2 C9 -133.87(12) . . . . ?
N1 C4 C5 C6 -177.54(14) . . . . ?
N2 C2 C3 C4 -105.23(13) . . . . ?
N2 C2 C3 C8 75.95(18) . . . . ?
N2 C2 C9 C10 7.40(13) . . . . ?
N2 C2 C9 C21 -110.57(12) . . . . ?
N2 C2 C9 C25 131.80(12) . . . . ?
N2 C11 C12 C13 -13.27(15) . . . . ?
N3 C7 C8 C3 -173.71(12) . . . . ?
C1 N1 C4 C3 -2.36(17) . . . . ?
C1 N1 C4 C5 177.46(14) . . . . ?
C1 C2 C3 C4 4.36(14) . . . . ?
C1 C2 C3 C8 -174.46(14) . . . . ?
C1 C2 C9 C10 -104.99(12) . . . . ?
C1 C2 C9 C21 137.05(12) . . . . ?
C1 C2 C9 C25 19.41(16) . . . . ?
C2 N2 C11 C10 39.82(13) . . . . ?
C2 N2 C11 C12 160.39(11) . . . . ?
C2 N2 C14 C13 -160.40(12) . . . . ?
C2 C3 C4 N1 -1.66(16) . . . . ?
C2 C3 C4 C5 178.51(13) . . . . ?
C2 C3 C8 C7 178.92(14) . . . . ?
C2 C9 C10 C11 16.10(13) . . . . ?
C2 C9 C10 C15 145.64(11) . . . . ?
C2 C9 C21 O2 98.14(15) . . . . ?
C2 C9 C21 C22 -82.05(14) . . . . ?
C2 C9 C25 C24 56.97(15) . . . . ?
C3 C2 C9 C10 136.62(12) . . . . ?
C3 C2 C9 C21 18.66(16) . . . . ?
C3 C2 C9 C25 -98.98(14) . . . . ?
C3 C4 C5 C6 2.3(2) . . . . ?
C4 N1 C1 O1 -178.18(14) . . . . ?
C4 N1 C1 C2 5.18(16) . . . . ?
C4 C3 C8 C7 0.2(2) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C5 C6 C7 N3 173.40(13) . . . . ?
C5 C6 C7 C8 -2.6(2) . . . . ?
C6 C7 C8 C3 2.3(2) . . . . ?
C8 C3 C4 N1 177.33(12) . . . . ?
C8 C3 C4 C5 -2.5(2) . . . . ?
C9 C2 C3 C4 128.25(13) . . . . ?
C9 C2 C3 C8 -50.6(2) . . . . ?
C9 C10 C11 N2 -34.53(13) . . . . ?
C9 C10 C11 C12 -148.95(12) . . . . ?
C9 C10 C15 C16 -93.10(17) . . . . ?
C9 C10 C15 C20 87.66(16) . . . . ?
C9 C21 C22 C23 3.60(18) . . . . ?
C9 C21 C22 C30 -179.73(12) . . . . ?
C10 C9 C21 O2 -14.38(18) . . . . ?
C10 C9 C21 C22 165.43(11) . . . . ?
C10 C9 C25 C24 174.46(11) . . . . ?
C10 C11 C12 C13 100.56(14) . . . . ?
C10 C15 C16 C17 179.70(14) . . . . ?
C10 C15 C20 C19 -178.76(14) . . . . ?
C11 N2 C2 C1 89.28(12) . . . . ?
C11 N2 C2 C3 -162.05(11) . . . . ?
C11 N2 C2 C9 -29.41(13) . . . . ?
C11 N2 C14 C13 -42.98(14) . . . . ?
C11 C10 C15 C16 31.04(19) . . . . ?
C11 C10 C15 C20 -148.19(13) . . . . ?
C11 C12 C13 C14 -12.56(15) . . . . ?
C12 C13 C14 N2 33.55(15) . . . . ?
C14 N2 C2 C1 -153.58(12) . . . . ?
C14 N2 C2 C3 -44.92(16) . . . . ?
C14 N2 C2 C9 87.73(14) . . . . ?
C14 N2 C11 C10 -85.19(13) . . . . ?
C14 N2 C11 C12 35.39(13) . . . . ?
C15 C10 C11 N2 -163.97(11) . . . . ?
C15 C10 C11 C12 81.60(15) . . . . ?
C15 C16 C17 C18 -0.7(2) . . . . ?
C16 C15 C20 C19 2.0(2) . . . . ?
C16 C17 C18 F1 -178.89(14) . . . . ?
C16 C17 C18 C19 1.6(2) . . . . ?
C17 C18 C19 C20 -0.7(2) . . . . ?
C18 C19 C20 C15 -1.1(2) . . . . ?
C20 C15 C16 C17 -1.1(2) . . . . ?
C21 C9 C10 C11 133.16(12) . . . . ?
C21 C9 C10 C15 -97.30(13) . . . . ?
C21 C9 C25 C24 -63.18(14) . . . . ?
C21 C22 C23 C24 -29.04(18) . . . . ?
C21 C22 C23 C26 146.38(14) . . . . ?
C21 C22 C30 C31 178.38(14) . . . . ?
C22 C23 C24 C25 4.83(19) . . . . ?
C22 C23 C24 C29 -179.46(13) . . . . ?
C22 C23 C26 C27 -179.60(14) . . . . ?
C22 C30 C31 C32 -30.6(2) . . . . ?
C22 C30 C31 C36 151.54(16) . . . . ?
C23 C22 C30 C31 -5.4(3) . . . . ?
C23 C24 C25 C9 42.99(17) . . . . ?
C23 C24 C29 C28 -2.0(2) . . . . ?
C23 C26 C27 C28 0.5(2) . . . . ?
C24 C23 C26 C27 -4.2(2) . . . . ?
C25 C9 C10 C11 -107.60(13) . . . . ?
C25 C9 C10 C15 21.94(16) . . . . ?
C25 C9 C21 O2 -139.13(13) . . . . ?
C25 C9 C21 C22 40.68(15) . . . . ?
C25 C24 C29 C28 173.55(14) . . . . ?
C26 C23 C24 C25 -170.78(13) . . . . ?
C26 C23 C24 C29 4.9(2) . . . . ?
C26 C27 C28 C29 2.5(2) . . . . ?
C27 C28 C29 C24 -1.8(2) . . . . ?
C29 C24 C25 C9 -132.62(14) . . . . ?
C30 C22 C23 C24 154.80(14) . . . . ?
C30 C22 C23 C26 -29.8(2) . . . . ?
C30 C31 C32 C33 179.26(13) . . . . ?
C30 C31 C36 C35 -178.15(13) . . . . ?
C31 C32 C33 C34 -0.4(2) . . . . ?
C32 C31 C36 C35 3.9(2) . . . . ?
C32 C33 C34 F2 -177.63(13) . . . . ?
C32 C33 C34 C35 3.0(2) . . . . ?
C33 C34 C35 C36 -2.1(2) . . . . ?
C34 C35 C36 C31 -1.4(2) . . . . ?
C36 C31 C32 C33 -2.9(2) . . . . ?
C37 O6 C39 C40 -171.2(5) . . . . ?
C39 O6 C37 O5 3.5(8) . . . . ?
C39 O6 C37 C38 179.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethylacetate and cyclohexane'
