# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_songnz_220307_2_auto
_database_code_depnum_ccdc_archive 'CCDC 2308902'
loop_
_audit_author_name
_audit_author_address
'Liping Zhu'
;Guangzhou University of Chinese Medicine, Guangzhou, Guang Dong
China
;
_audit_update_record             
;
2023-11-19 deposited with the CCDC.	2024-02-06 downloaded from the CCDC.
;
_audit_creation_date             2022-03-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
3-benzoyl-1-(4-fluorophenyl)-9-methyl-1,5,6,10b-tetrahydro-[1,2,4]triazolo[5,1-a]isoquinolin-2(3H)-one
_chemical_formula_moiety         'C24 H20 F N3 O2'
_chemical_formula_sum            'C24 H20 F N3 O2'
_chemical_formula_weight         401.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
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'
F F 0.0727 0.0534 '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'

_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                   9.5606(2)
_cell_length_b                   22.0542(4)
_cell_length_c                   9.7194(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.419(2)
_cell_angle_gamma                90
_cell_volume                     1944.36(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8871
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7380
_cell_measurement_theta_min      3.9760
_shelx_estimated_absorpt_T_max   0.892
_shelx_estimated_absorpt_T_min   0.829
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13017
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.860
_diffrn_reflns_theta_min         4.009
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00  61.00   0.50    0.10    --   45.78  41.00 -62.00   58
  2  ω     65.00 106.00   0.50    0.10    --   45.78  41.00 -62.00   82
  3  ω    103.00 129.00   0.50    0.40    --  105.53  41.00 -62.00   52
  4  ω    152.00 177.00   0.50    0.40    --  105.53  41.00 -62.00   50
  5  ω     96.00 177.00   0.50    0.40    --  105.53  30.00  30.00  162
  6  ω      1.00  45.00   0.50    0.10    --   45.78 -41.00 144.00   88
  7  ω     32.00  64.00   0.50    0.40    --  105.53 -61.00 150.00   64
  8  ω     32.00  73.00   0.50    0.40    --  105.53 -61.00  90.00   82
  9  ω    -26.00   0.00   0.50    0.10    --   45.78 -41.00 144.00   52
 10  ω     33.00  72.00   0.50    0.40    --  105.53 -61.00  30.00   78
 11  ω     38.00  67.00   0.50    0.40    --  105.53 -61.00   0.00   58
 12  ω     66.00 107.00   0.50    0.40    --  105.53 -77.00-120.00   82
 13  ω     33.00  71.00   0.50    0.40    --  105.53 -61.00-150.00   76
 14  ω    -42.00  28.00   0.50    0.10    --  -45.78  41.00 -62.00  140
 15  ω    -60.00 -30.00   0.50    0.40    -- -100.00  61.00-120.00   60
 16  ω    -69.00 -34.00   0.50    0.40    -- -100.00  61.00 -60.00   70
 17  ω    -93.00 -14.00   0.50    0.10    --  -45.78 125.00  30.00  158
 18  ω     36.00  94.00   0.50    0.40    --  105.53 -94.00   0.00  116
 19  ω    -67.00 -27.00   0.50    0.40    -- -100.00  61.00 120.00   80
 20  ω   -122.00 -95.00   0.50    0.40    -- -100.00 -30.00  60.00   54
 21  ω    -84.00 -58.00   0.50    0.10    --  -45.78 -41.00 144.00   52
 22  ω   -173.00 -86.00   0.50    0.40    -- -100.00 -41.00 144.00  174
 23  ω   -172.00-147.00   0.50    0.40    -- -100.00 -30.00  60.00   50
 24  ω   -166.00-100.00   0.50    0.40    -- -100.00 -94.00-120.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0179255000
_diffrn_orient_matrix_UB_12      -0.0271833000
_diffrn_orient_matrix_UB_13      0.1395078000
_diffrn_orient_matrix_UB_21      -0.1540775000
_diffrn_orient_matrix_UB_22      -0.0237424000
_diffrn_orient_matrix_UB_23      -0.0873351000
_diffrn_orient_matrix_UB_31      0.0691297000
_diffrn_orient_matrix_UB_32      -0.0598022000
_diffrn_orient_matrix_UB_33      -0.0287806000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3372
_reflns_number_total             3860
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3860
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.061
_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)+(0.0602P)²+0.4290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1118
_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.a Ternary CH refined with riding coordinates:
 C00E(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00L(H00C,H00F), C00O(H00G,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00D(H00D), C00I(H00I), C00J(H00J),
 C00M(H00M), C00N(H00N), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T)
2.d Idealised Me refined as rotating group:
 C00U(H00K,H00L,H00O)
;
_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
F001 F 0.53211(10) 0.51022(3) 0.31937(9) 0.0343(2) Uani 1 1 d . . . . .
O002 O 0.45336(10) 0.23437(4) 0.33685(9) 0.0240(2) Uani 1 1 d . . . . .
O003 O 0.56078(12) 0.08467(4) 0.61558(11) 0.0339(3) Uani 1 1 d . . . . .
N004 N 0.51489(12) 0.28401(4) 0.55899(11) 0.0213(2) Uani 1 1 d . . . . .
N005 N 0.54777(12) 0.18439(5) 0.55999(12) 0.0241(3) Uani 1 1 d . . . . .
N006 N 0.56187(12) 0.20009(5) 0.70678(12) 0.0246(2) Uani 1 1 d . . . . .
C007 C 0.51982(14) 0.34352(5) 0.50090(13) 0.0204(3) Uani 1 1 d . . . . .
C008 C 0.49902(14) 0.23496(5) 0.46819(13) 0.0206(3) Uani 1 1 d . . . . .
C009 C 0.39020(15) 0.36957(6) 0.41319(13) 0.0224(3) Uani 1 1 d . . . . .
H009 H 0.299142 0.348792 0.395356 0.027 Uiso 1 1 calc R U . . .
C00A C 0.65424(15) 0.37315(6) 0.52564(14) 0.0232(3) Uani 1 1 d . . . . .
H00A H 0.742941 0.354569 0.583584 0.028 Uiso 1 1 calc R U . . .
C00B C 0.39397(15) 0.42628(6) 0.35137(14) 0.0247(3) Uani 1 1 d . . . . .
H00B H 0.306094 0.444692 0.291158 0.030 Uiso 1 1 calc R U . . .
C00C C 0.52773(16) 0.45503(5) 0.37944(14) 0.0253(3) Uani 1 1 d . . . . .
C00D C 0.65809(16) 0.43005(6) 0.46520(14) 0.0259(3) Uani 1 1 d . . . . .
H00D H 0.748619 0.451189 0.482693 0.031 Uiso 1 1 calc R U . . .
C00E C 0.60196(14) 0.26439(6) 0.70854(13) 0.0221(3) Uani 1 1 d . . . . .
H00E H 0.709120 0.267153 0.718508 0.026 Uiso 1 1 calc R U . . .
C00F C 0.55951(15) 0.12373(6) 0.52610(16) 0.0270(3) Uani 1 1 d . . . . .
C00G C 0.57573(14) 0.29867(6) 0.83303(14) 0.0255(3) Uani 1 1 d . . . . .
C00H C 0.57905(15) 0.10910(6) 0.38372(15) 0.0270(3) Uani 1 1 d . . . . .
C00I C 0.63387(15) 0.35688(6) 0.86649(14) 0.0274(3) Uani 1 1 d . . . . .
H00I H 0.684164 0.374984 0.806881 0.033 Uiso 1 1 calc R U . . .
C00J C 0.66870(15) 0.14402(6) 0.32648(16) 0.0291(3) Uani 1 1 d . . . . .
H00J H 0.708571 0.181073 0.372027 0.035 Uiso 1 1 calc R U . . .
C00K C 0.50375(16) 0.27098(7) 0.92150(15) 0.0310(3) Uani 1 1 d . . . . .
C00L C 0.41730(16) 0.19161(7) 0.73082(15) 0.0296(3) Uani 1 1 d . . . . .
H00C H 0.385216 0.148835 0.713309 0.036 Uiso 1 1 calc R U . . .
H00F H 0.341646 0.217665 0.663767 0.036 Uiso 1 1 calc R U . . .
C00M C 0.52070(17) 0.05472(6) 0.31671(17) 0.0329(3) Uani 1 1 d . . . . .
H00M H 0.461203 0.030174 0.356262 0.040 Uiso 1 1 calc R U . . .
C00N C 0.70021(17) 0.12506(7) 0.20333(17) 0.0343(3) Uani 1 1 d . . . . .
H00N H 0.762719 0.148721 0.165595 0.041 Uiso 1 1 calc R U . . .
C00O C 0.43705(18) 0.20891(7) 0.88640(16) 0.0362(3) Uani 1 1 d . . . . .
H00G H 0.340088 0.208123 0.902988 0.043 Uiso 1 1 calc R U . . .
H00H H 0.501619 0.178809 0.952065 0.043 Uiso 1 1 calc R U . . .
C00P C 0.62025(16) 0.38922(7) 0.98492(15) 0.0341(3) Uani 1 1 d . . . . .
C00Q C 0.55016(18) 0.03667(6) 0.19172(18) 0.0378(4) Uani 1 1 d . . . . .
H00Q H 0.508358 0.000206 0.144311 0.045 Uiso 1 1 calc R U . . .
C00R C 0.64014(18) 0.07150(7) 0.13563(17) 0.0376(4) Uani 1 1 d . . . . .
H00R H 0.660614 0.058609 0.050702 0.045 Uiso 1 1 calc R U . . .
C00S C 0.49594(17) 0.30246(9) 1.04353(16) 0.0398(4) Uani 1 1 d . . . . .
H00S H 0.451551 0.283615 1.107260 0.048 Uiso 1 1 calc R U . . .
C00T C 0.55134(17) 0.36024(8) 1.07309(16) 0.0405(4) Uani 1 1 d . . . . .
H00T H 0.542329 0.380847 1.155708 0.049 Uiso 1 1 calc R U . . .
C00U C 0.68171(19) 0.45222(8) 1.01777(18) 0.0429(4) Uani 1 1 d . . . . .
H00K H 0.787918 0.451504 1.032357 0.064 Uiso 1 1 calc R U . . .
H00L H 0.664312 0.467152 1.105933 0.064 Uiso 1 1 calc R U . . .
H00O H 0.632976 0.479096 0.936440 0.064 Uiso 1 1 calc R U . . .


_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
F001 C00C 1.3563(14) . ?
O002 C008 1.2117(15) . ?
O003 C00F 1.2214(17) . ?
N004 C007 1.4355(15) . ?
N004 C008 1.3738(15) . ?
N004 C00E 1.4927(16) . ?
N005 N006 1.4325(15) . ?
N005 C008 1.4123(16) . ?
N005 C00F 1.3907(16) . ?
N006 C00E 1.4677(16) . ?
N006 C00L 1.4846(18) . ?
C007 C009 1.3874(18) . ?
C007 C00A 1.3933(18) . ?
C009 H009 0.9500 . ?
C009 C00B 1.3930(17) . ?
C00A H00A 0.9500 . ?
C00A C00D 1.3908(18) . ?
C00B H00B 0.9500 . ?
C00B C00C 1.375(2) . ?
C00C C00D 1.377(2) . ?
C00D H00D 0.9500 . ?
C00E H00E 1.0000 . ?
C00E C00G 1.5133(17) . ?
C00F C00H 1.489(2) . ?
C00G C00I 1.396(2) . ?
C00G C00K 1.4000(19) . ?
C00H C00J 1.392(2) . ?
C00H C00M 1.3944(19) . ?
C00I H00I 0.9500 . ?
C00I C00P 1.3947(19) . ?
C00J H00J 0.9500 . ?
C00J C00N 1.388(2) . ?
C00K C00O 1.503(2) . ?
C00K C00S 1.397(2) . ?
C00L H00C 0.9900 . ?
C00L H00F 0.9900 . ?
C00L C00O 1.512(2) . ?
C00M H00M 0.9500 . ?
C00M C00Q 1.389(2) . ?
C00N H00N 0.9500 . ?
C00N C00R 1.385(2) . ?
C00O H00G 0.9900 . ?
C00O H00H 0.9900 . ?
C00P C00T 1.391(2) . ?
C00P C00U 1.503(2) . ?
C00Q H00Q 0.9500 . ?
C00Q C00R 1.387(3) . ?
C00R H00R 0.9500 . ?
C00S H00S 0.9500 . ?
C00S C00T 1.375(3) . ?
C00T H00T 0.9500 . ?
C00U H00K 0.9800 . ?
C00U H00L 0.9800 . ?
C00U H00O 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
C007 N004 C00E 124.79(10) . . ?
C008 N004 C007 118.55(10) . . ?
C008 N004 C00E 108.17(10) . . ?
C008 N005 N006 110.29(10) . . ?
C00F N005 N006 118.63(10) . . ?
C00F N005 C008 130.19(11) . . ?
N005 N006 C00E 100.79(9) . . ?
N005 N006 C00L 109.09(10) . . ?
C00E N006 C00L 111.87(11) . . ?
C009 C007 N004 119.10(11) . . ?
C009 C007 C00A 120.53(11) . . ?
C00A C007 N004 120.27(11) . . ?
O002 C008 N004 127.97(11) . . ?
O002 C008 N005 126.45(11) . . ?
N004 C008 N005 105.58(10) . . ?
C007 C009 H009 120.1 . . ?
C007 C009 C00B 119.80(12) . . ?
C00B C009 H009 120.1 . . ?
C007 C00A H00A 120.1 . . ?
C00D C00A C007 119.75(12) . . ?
C00D C00A H00A 120.1 . . ?
C009 C00B H00B 120.7 . . ?
C00C C00B C009 118.52(12) . . ?
C00C C00B H00B 120.7 . . ?
F001 C00C C00B 118.79(12) . . ?
F001 C00C C00D 118.33(12) . . ?
C00B C00C C00D 122.88(12) . . ?
C00A C00D H00D 120.8 . . ?
C00C C00D C00A 118.49(12) . . ?
C00C C00D H00D 120.8 . . ?
N004 C00E H00E 108.4 . . ?
N004 C00E C00G 116.84(10) . . ?
N006 C00E N004 101.85(9) . . ?
N006 C00E H00E 108.4 . . ?
N006 C00E C00G 112.54(10) . . ?
C00G C00E H00E 108.4 . . ?
O003 C00F N005 119.55(13) . . ?
O003 C00F C00H 122.20(12) . . ?
N005 C00F C00H 118.14(11) . . ?
C00I C00G C00E 119.43(12) . . ?
C00I C00G C00K 119.67(13) . . ?
C00K C00G C00E 120.73(13) . . ?
C00J C00H C00F 121.69(12) . . ?
C00J C00H C00M 119.67(13) . . ?
C00M C00H C00F 118.12(13) . . ?
C00G C00I H00I 119.0 . . ?
C00P C00I C00G 121.90(14) . . ?
C00P C00I H00I 119.0 . . ?
C00H C00J H00J 119.8 . . ?
C00N C00J C00H 120.45(13) . . ?
C00N C00J H00J 119.8 . . ?
C00G C00K C00O 120.90(13) . . ?
C00S C00K C00G 118.25(15) . . ?
C00S C00K C00O 120.85(13) . . ?
N006 C00L H00C 110.3 . . ?
N006 C00L H00F 110.3 . . ?
N006 C00L C00O 107.29(12) . . ?
H00C C00L H00F 108.5 . . ?
C00O C00L H00C 110.3 . . ?
C00O C00L H00F 110.3 . . ?
C00H C00M H00M 120.2 . . ?
C00Q C00M C00H 119.55(14) . . ?
C00Q C00M H00M 120.2 . . ?
C00J C00N H00N 120.1 . . ?
C00R C00N C00J 119.75(15) . . ?
C00R C00N H00N 120.1 . . ?
C00K C00O C00L 111.51(12) . . ?
C00K C00O H00G 109.3 . . ?
C00K C00O H00H 109.3 . . ?
C00L C00O H00G 109.3 . . ?
C00L C00O H00H 109.3 . . ?
H00G C00O H00H 108.0 . . ?
C00I C00P C00U 121.06(15) . . ?
C00T C00P C00I 117.35(15) . . ?
C00T C00P C00U 121.56(14) . . ?
C00M C00Q H00Q 119.8 . . ?
C00R C00Q C00M 120.50(14) . . ?
C00R C00Q H00Q 119.8 . . ?
C00N C00R C00Q 120.06(15) . . ?
C00N C00R H00R 120.0 . . ?
C00Q C00R H00R 120.0 . . ?
C00K C00S H00S 119.4 . . ?
C00T C00S C00K 121.18(14) . . ?
C00T C00S H00S 119.4 . . ?
C00P C00T H00T 119.2 . . ?
C00S C00T C00P 121.56(14) . . ?
C00S C00T H00T 119.2 . . ?
C00P C00U H00K 109.5 . . ?
C00P C00U H00L 109.5 . . ?
C00P C00U H00O 109.5 . . ?
H00K C00U H00L 109.5 . . ?
H00K C00U H00O 109.5 . . ?
H00L C00U H00O 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
F001 C00C C00D C00A -179.28(11) . . . . ?
O003 C00F C00H C00J -136.91(14) . . . . ?
O003 C00F C00H C00M 34.81(19) . . . . ?
N004 C007 C009 C00B -177.50(11) . . . . ?
N004 C007 C00A C00D 178.09(11) . . . . ?
N004 C00E C00G C00I -74.86(15) . . . . ?
N004 C00E C00G C00K 110.03(14) . . . . ?
N005 N006 C00E N004 35.13(11) . . . . ?
N005 N006 C00E C00G 161.04(10) . . . . ?
N005 N006 C00L C00O -179.76(10) . . . . ?
N005 C00F C00H C00J 39.45(18) . . . . ?
N005 C00F C00H C00M -148.83(13) . . . . ?
N006 N005 C008 O002 -167.00(12) . . . . ?
N006 N005 C008 N004 13.16(14) . . . . ?
N006 N005 C00F O003 10.15(19) . . . . ?
N006 N005 C00F C00H -166.31(11) . . . . ?
N006 C00E C00G C00I 167.79(11) . . . . ?
N006 C00E C00G C00K -7.31(17) . . . . ?
N006 C00L C00O C00K 52.79(16) . . . . ?
C007 N004 C008 O002 -19.5(2) . . . . ?
C007 N004 C008 N005 160.37(11) . . . . ?
C007 N004 C00E N006 -176.88(11) . . . . ?
C007 N004 C00E C00G 60.08(16) . . . . ?
C007 C009 C00B C00C 0.05(18) . . . . ?
C007 C00A C00D C00C -1.30(18) . . . . ?
C008 N004 C007 C009 75.12(15) . . . . ?
C008 N004 C007 C00A -101.24(14) . . . . ?
C008 N004 C00E N006 -29.69(12) . . . . ?
C008 N004 C00E C00G -152.73(11) . . . . ?
C008 N005 N006 C00E -31.24(13) . . . . ?
C008 N005 N006 C00L 86.61(12) . . . . ?
C008 N005 C00F O003 -157.87(13) . . . . ?
C008 N005 C00F C00H 25.7(2) . . . . ?
C009 C007 C00A C00D 1.77(18) . . . . ?
C009 C00B C00C F001 179.91(11) . . . . ?
C009 C00B C00C C00D 0.41(19) . . . . ?
C00A C007 C009 C00B -1.14(18) . . . . ?
C00B C00C C00D C00A 0.2(2) . . . . ?
C00E N004 C007 C009 -140.77(12) . . . . ?
C00E N004 C007 C00A 42.86(17) . . . . ?
C00E N004 C008 O002 -169.02(13) . . . . ?
C00E N004 C008 N005 10.82(13) . . . . ?
C00E N006 C00L C00O -69.12(13) . . . . ?
C00E C00G C00I C00P -176.35(12) . . . . ?
C00E C00G C00K C00O -6.3(2) . . . . ?
C00E C00G C00K C00S 173.52(12) . . . . ?
C00F N005 N006 C00E 158.50(11) . . . . ?
C00F N005 N006 C00L -83.65(14) . . . . ?
C00F N005 C008 O002 1.8(2) . . . . ?
C00F N005 C008 N004 -178.05(13) . . . . ?
C00F C00H C00J C00N 171.61(13) . . . . ?
C00F C00H C00M C00Q -173.28(13) . . . . ?
C00G C00I C00P C00T 2.6(2) . . . . ?
C00G C00I C00P C00U -179.08(13) . . . . ?
C00G C00K C00O C00L -17.35(19) . . . . ?
C00G C00K C00S C00T 2.9(2) . . . . ?
C00H C00J C00N C00R 1.0(2) . . . . ?
C00H C00M C00Q C00R 1.7(2) . . . . ?
C00I C00G C00K C00O 178.62(12) . . . . ?
C00I C00G C00K C00S -1.6(2) . . . . ?
C00I C00P C00T C00S -1.3(2) . . . . ?
C00J C00H C00M C00Q -1.4(2) . . . . ?
C00J C00N C00R C00Q -0.7(2) . . . . ?
C00K C00G C00I C00P -1.2(2) . . . . ?
C00K C00S C00T C00P -1.5(2) . . . . ?
C00L N006 C00E N004 -80.67(12) . . . . ?
C00L N006 C00E C00G 45.25(14) . . . . ?
C00M C00H C00J C00N 0.0(2) . . . . ?
C00M C00Q C00R C00N -0.7(2) . . . . ?
C00O C00K C00S C00T -177.30(14) . . . . ?
C00S C00K C00O C00L 162.86(13) . . . . ?
C00U C00P C00T C00S -179.59(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.840
_oxdiff_exptl_absorpt_empirical_full_min 0.399
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
